Abstract:
Disclosed are methods of purifying the compound (20R)-2-methylene-19-nor-24-difluoro-1α,25-dihydroxyvitamin D 3  to obtain the compound in crystalline form. The methods typically include the steps of dissolving a product containing the compound in a solvent comprising hexane and 2-propanol, cooling the solvent and dissolved product below ambient temperature for a sufficient amount of time to form a precipitate of crystals, and recovering the crystals.

Description:
CROSS-REFERENCE TO RELATED PATENT APPLICATIONS 
     The present application claims the benefit under 35 U.S.C. §119(e) to U.S. Provisional Patent Application Ser. No. 61/652,959, filed on May 30,2012, the content of which is incorporated herein by reference in its entirety. 
    
    
     STATEMENT REGARDING FEDERALLY SPONSORED RESEARCH OR DEVELOPMENT 
     This invention was made with government support under DK047814 awarded by the National Institutes of Health. The government has certain rights in the invention. 
    
    
     BACKGROUND 
     The field of the present invention relates to purification of organic compounds, and more particularly to the purification of the compound (20R)-2-methylene-19-nor-24-difluoro-1α,25-dihydroxyvitamin D 3  (referred to herein as “F-24”) by preparing the compound in crystalline form. 
     Purification of organic compounds, especially those designated for pharmaceutical use, is of considerable importance for chemists synthesizing such compounds. Preparation of the compound usually requires many synthetic steps and, therefore, the final product can be contaminated not only with side-products derived from the last synthetic step of the procedure but also with compounds that were formed in previous steps. Even chromatographic purification, which is a very efficient but relatively time-consuming process, does not usually provide compounds which are sufficiently pure to be used as drugs. 
     Depending on the method used to synthesize 1α-hydroxyvitamin D compounds, different minor undesirable compounds can accompany the final product. Thus, for example, if direct C-1 hydroxylation of the 5,6-trans geometric isomer of vitamin D is performed, followed by SeO 2 /NMO oxidation and photochemical irradiation, (see Andrews et al.,  J. Org. Chem.  51, 1635 (1986); Calverley et al.,  Tetrahedron  43, 4609 (1987); Choudry et al.,  J. Org. Chem.  58, 1496 (1993)), the final 1α-hydroxyvitamin D product can be contaminated with 1β-hydroxy- as well as 5,6-trans isomers. If the method consists of C-1 allylic oxidation of the 4-phenyl-1,2,4-triazoline-3,5-dione adduct of the pre-vitamin D compound, followed by cycloreversion of the modified adduct under basic conditions, (see Nevinekx et al.,  Tetrahedron  47, 9419 (1991); Vanmaele et al.,  Tetrahedron  41, 141 (1985) and 40, 1179 (1994); Vanmaele el al.,  Tetrahedron Lett.  23, 995 (1982)), one can expect that the desired 1α-hydroxyvitamin can be contaminated with the pre-vitamin 5(10), 6,8-triene and 1β-hydroxy isomer. One of the most useful C-1 hydroxylation methods, of very broad scope and numerous applications, is the experimentally simple procedure elaborated by Paaren et al.,  J. Org. Chem.  45, 3253 (1980); and  Proc. Natl. Acad. Set U.S.A.  75, 2080 (1978). This method consists of allylic oxidation of 3,5-cyclovitamin D derivatives, readily obtained from the buffered solvolysis of vitamin D tosylates, with SeO 2 /t-BuOOH and subsequent acid-catalyzed cycloreversion to the desired 1α-hydroxy compounds. Taking into account this synthetic path it is reasonable to assume that the final product can be contaminated with the 1α-hydroxy epimer, the 5,6-trans isomer and the pre-vitamin D form. 1α-hydroxyvitamin D 4  is another undesirable contaminant found in 1α-hydroxyvitamin D compounds synthesized from vitamin D 2  or from ergosterol. 1α-hydroxy vitamin D 4  results from C-1 oxidation of vitamin D 4 , which in turn is derived from contamination of the commercial ergosterol material. Typically, the final product may contain up to about 1.5% by weight 1α-hydroxyvitamin D 4 . Thus, a purification technique that would eliminate or substantially reduce the amount of 1α-hydroxyvitamin D 4  in the final product to less than about 0.1-0.2% would be highly desirable. 
     The vitamin D conjugated triene system is not only heat- and light-sensitive but it is also prone to oxidation, leading to the complex mixture of very polar compounds. Oxidation usually happens when a vitamin D compound has been stored for a prolonged time. Other types of processes that can lead to a partial decomposition of vitamin D compounds consist of some water-elimination reactions. The driving force for these reactions is the allylic (1α-) and homoallylic (3β-) position of the hydroxy groups. The presence of such above-mentioned oxidation and elimination products can be easily detected by thin-layer chromatography. 
     Usually, all 1α-hydroxylatation procedures require at least one chromatographic purification. However, even chromatographically purified 1α-hydroxyvitamin D compounds, although showing consistent spectroscopic data that suggests homogeneity, do not meet the purity criteria required for therapeutic agents that can be orally, parenterally or transdermally administered. Therefore, it is evident that a suitable method of purification of the 1α-hydroxylated vitamin D compound F-24 is required. 
     SUMMARY 
     Disclosed herein are methods of purifying F-24 by means of crystallization to obtain F-24 in crystalline form. The solvent plays an important role in the crystallization process, and is typically an individual liquid substance or a suitable mixture of different liquids. For crystallizing F-24, the most appropriate solvent and/or solvent system is characterized by the following factors;
         (1) low toxicity;   (2) low boiling point;   (3) significant dependence of solubility properties with regard to temperature (condition necessary for providing satisfactory crystallization yield); and   (4) relatively low cost.       

     Interestingly, hexane, so frequently used for crystallization purposes, was found less suitable as the sole solvent for crystallization of F-24. However, it was found that a mixture of 2-propanol and hexane was most useful for the crystallization of F-24. In particular, it was determined that a mixture of about 10% to about 20% 2-propanol (v/v) with about 90% to about 80% hexane (v/v) (and preferably 15% 2-propanol (v/v) with about 85% hexane (v/v)) performed well. The 2-propanol/hexane solvent mixture also was easy to remove by evaporation or other well-known methods. In all cases, the crystallization process occurred easily and efficiently. The precipitated crystals were sufficiently large to assure their recovery by filtration or other means, and thus were suitable for x-ray analysis. 
     Accordingly, disclosed herein is a compound having the formula: 
                                
in crystalline form. More specifically, the compound may be referred to as (20R)-2-methylene-19-nor-24-difluoro-1a-25-dihydroxyvitamin D 3  or “F-24” in crystalline form.
 
    
    
     
       BRIEF DESCRIPTION OF THE DRAWINGS 
         FIG. 1  is an illustration of the three dimensional molecular structure for F-24 as defined by the atomic positional parameters discovered and set forth herein, 
     
    
    
     DETAILED DESCRIPTION 
     Disclosed herein is the compound (20R)-2-methylene-19-nor-24-difluoro-1α,25-dihydroxyvitamin D3 (F-24) in crystalline form, a pharmacologically important compound, characterized by the formula I shown below: 
     
       
                 
         
             
             
         
      
     
     Also disclosed are methods of purifying F-24. The purification technique involves obtaining the F-24 product in crystalline form by utilizing a crystallization procedure wherein the material to be purified is dissolved using as the solvent a mixture comprised of 2-propanol and hexane to obtain F-24. Preferably the mixture comprises from about 10% to about 20% 2-propanol and about 90% to about 80% hexane, and preferably about 15% 2-propanol and about 85% hexane (by volume). Thereafter, the solvent can be removed by evaporation, with or without vacuum, or other means as is well known, or the resultant crystals may be filtered from the mother liquor. The technique can be used to purify a wide range of final products containing F-24 obtained from any known synthesis thereof, and in varying concentrations, ranging from microgram amounts to kilogram amounts. As is well known to those skilled in this art, the amount of solvent utilized may be modulated according to the amount of F-24 to be purified. 
     EXAMPLES 
     The following examples are illustrative and should not be interpreted as limiting the claimed subject matter. 
     The usefulness and advantages of the present crystallization procedure is shown in the following specific Examples. After crystallization, the precipitated material was observed under a microscope to confirm its crystalline form. Yields of crystals were relatively high and the obtained crystals showed a relatively sharp melting point of 163-164° C. (F-24). 
     The described crystallization process of the synthetic F-24 product represents a valuable purification method, which can remove most side products derived from the synthetic path. Such impurity is the result of the contamination of starting raw materials. The crystallization process occurred easily and efficiently. The precipitated crystals were sufficiently large to assure their recovery by filtration, or other means, and thus were suitable for x-ray analysis, 
     Example  1   
     Crystallization of (20R)-2-methylene-19-nor-24-difluoro-1α,25-dihydroxyvitamin D 3  (F-24) 
     Crystallization from 2-propanol/hexane, (20R)-2-methylene-19-nor-24-difluoro-1α,25-dihydroxyvitamin D3 (9 mg), was suspended in hexane (4 mL) and then 2-propanol was added dropwise to the suspension. The mixture was heated in a water bath to dissolve the vitamin, then was left at room temperature for about 1 hour, and finally was kept in a refrigerator for about 48 hours. The precipitated crystals were filtered off, washed with a small volume of a cold (0° C.) 2-propanol/hexane (3:1) mixture, and dried to give crystalline material. It should be noted that an excess of 2-propanol should be avoided to get the point of saturation, (i.e., only about 1 mole or less of 2-propanol should be added). 
     Experimental. A colorless prism-shaped crystal of dimensions 0.42×0.01×0.01 mm was selected for structural analysis. Intensity data were collected using a Broker AXS Platinum 135 CCD detector controlled with the PROTEUM software suite (Broker AXS Inc., Madison, Wis.). The x-ray source was CuKα radiation (1.54178Å) from a Rigaku RU200 x-ray generator equipped with Montel optics, operated at 50 kV and 90 mA. The x-ray data were processed with SAINT version 7.06A. (Broker AXS Inc.) and internally scaled with SADABS version 2005/1 (Broker AXS Inc.). The sample was mounted in a glass fiber and diffraction data collected at 100 K. The intensity data were measured as a series of phi and omega oscillation frames each of 1° for 90-180 sec/frame. The detector was operated in 1024×1024 mode and was positioned 5.0 cm from the sample. Cell parameters were determined from a non-linear least squares fit of 8490 peaks in the range of 2.65&lt;theta&lt;49.14°. The data were merged to form a set of 1.310 independent data with R(int)=0.0920. 
     The monoclinic space group C2 was determined by systematic absences and statistical tests and verified by subsequent refinement. The structure was solved by direct methods and refined by full-matrix least-squares methods on F 2 , (a) G. M. Sheldrick (1994), SHELXTL Version 5 Reference Manual, Broker AXS Inc.; (b)  International Tables for Crystallography, Vol. C , Kluwer: Boston (1995). Hydrogen atom positions were determined from difference peaks and ultimately refined by a riding model with idealized geometry. Non-hydrogen atoms were refined with anisotropic displacement parameters. A total of 290 parameters were refined against 1 restraint and 1310 data to give wR2=0.1867 and S=1.022 for weights of w=1/[s 2 (F 2 )+(0.1.139P) 2 ], where P=[F o   2 +2F c   2 ]/3. The final R(F) was 0.0669 for the 1310 observed data. The largest shift/s.u. was 0.001 in the final refinement cycle and the final difference map had maxima and minima of 0.256 and −0.238 e/Å 3 , respectively. The absolute structure was determined by refinement of the Flack parameter, H. D. Flack,  Acta Cryst. A , vol. 39, 876-881 (1983). 
     The three dimensional structure of F-24 as defined by the following physical data and atomic positional parameters described and calculated herein (Tables 1-8) is illustrated in  FIG. 1 . 
     
       
         
               
             
               
               
             
           
               
                 TABLE 1 
               
               
                   
               
               
                 Crystal data and structure refinement for F-24. 
               
               
                   
               
             
             
               
                   
               
             
          
           
               
                 Identification code 
                 03dec2010 
               
               
                 Empirical formula 
                 C27H42F2O3 
               
               
                 Formula weight 
                  452.61 
               
               
                 Temperature 
                 100 (1) K 
               
               
                 Wavelength 
                   1.54178 Å 
               
               
                 Crystal system 
                 Monoclinic 
               
               
                 Space group 
                 C2 
               
               
                 Unit cell dimensions 
                 a = 23.845 (5) Å α = 90° 
               
               
                   
                 b = 6.2760 (13) Å β = 126.52 (3)° 
               
               
                   
                 c = 20.711 (4) Å γ = 90° 
               
               
                 Volume 
                 2490.9 (9) Å 3   
               
               
                 z 
                   4 
               
               
                 Density (calculated) 
                   1.207 Mg/m 3   
               
               
                 Absorption coefficient 
                   0.701 mm −1   
               
               
                 F (000) 
                  984 
               
               
                 Crystal size 
                 0.40 × 0.01 × 0.01 mm 
               
               
                 Theta range for data collection 
                 2.65 to 49.14° 
               
               
                 Limiting indices 
                 −23 &lt;= h &lt;= 18, 0 &lt;= k &lt;= 5, 0 &lt;= &lt;= 20 
               
               
                 Reflections collected 
                 8490 
               
               
                 Independent reflections 
                 1310 (R (int) = 0.0920) 
               
               
                 Completeness to Theta = 25.00 
                  100.0% 
               
               
                 Max. and min. transmission 
                 0.9930 and 0.7669 
               
               
                 Refinement method 
                 Full-matrix least-squares on F 2   
               
               
                 Data/restraints/parameters 
                 1310/1/290 
               
               
                 Goodness-of-fit on F 2   
                   1.022 
               
               
                 Final R indices [ I &gt; 2σ (I) ] 
                 R1 = 0.0825, wR2 = 0.1867 
               
               
                 R indices (all data) 
                 R1 = 0.1443, wR2 = 0.2297 
               
               
                 Largest diff. peak and hole 
                 0.256 and −0.238 e/Å 3   
               
               
                   
               
             
          
         
       
     
     
       
         
               
             
               
               
               
               
               
             
               
               
               
               
               
               
               
             
           
               
                 TABLE 2 
               
             
             
               
                   
               
               
                 Atomic coordinates (Å 2  × 10 4 ) and equivalent isotropic displacement parameters (Å 2  × 
               
               
                 10 3 ) for F-24 U(eq) is defined as one third of the trace of the orthogonalized Uij tensor. 
               
             
          
           
               
                   
                 x 
                 y 
                 z 
                 U (eq) 
               
               
                   
               
             
          
           
               
                 F (1) 
                 4444  
                 (4) 
                 7976 (17) 
                 1353  
                 (5) 
                 95 (3) 
               
               
                 F (2) 
                 4760  
                 (4) 
                 5304 (17) 
                 2162  
                 (5) 
                 90 (3) 
               
               
                 O (1) 
                 −1550  
                 (4) 
                 9715 (18) 
                 −4277  
                 (5) 
                 77 (3) 
               
               
                 O (3) 
                 −1985  
                 (5) 
                 3588 (18) 
                 −5182 
                 (6) 
                 83 (4) 
               
               
                 O (25) 
                 6102  
                 (5) 
                 5430 (20) 
                 2627  
                 (6) 
                 82 (3) 
               
               
                 C (14) 
                 1622  
                 (7) 
                 3190 (30) 
                 −1945  
                 (9) 
                 63 (4) 
               
               
                 C (13) 
                 2367 
                 (7) 
                 2780 (30) 
                 −1733  
                 (8) 
                 59 (5) 
               
               
                 C (4) 
                 −1165  
                 (7) 
                 4840 (30) 
                 −5413  
                 (8) 
                 74 (5) 
               
               
                 C (10) 
                 −681 
                 (7) 
                 7630 (30) 
                 −4283 
                 (8) 
                 72 (5) 
               
               
                 C (5) 
                 −578  
                 (7) 
                 5360 (30) 
                 −4551  
                 (9) 
                 69 (5) 
               
               
                 C (9) 
                 1057  
                 (7) 
                  680 (30) 
                 −3085 
                 (9) 
                 69 (5) 
               
               
                 C (27) 
                 5839  
                 (7) 
                 8160 (30) 
                 1701  
                 (8) 
                 88 (6) 
               
               
                 C (17) 
                 2833 
                 (7) 
                 3210 (30) 
                 −814  
                 (8) 
                 66 (4) 
               
               
                 C (1) 
                 −1423  
                 (8) 
                 7730 (30) 
                 −4521  
                 (9) 
                 68 (5) 
               
               
                 C (2) 
                 −1957  
                 (8) 
                 7350 (30) 
                 −5422  
                 (10) 
                 70 (6) 
               
               
                 C (19) 
                 −2400  
                 (8) 
                 8730 (30) 
                 −5961  
                 (9)  
                 80 (5) 
               
               
                 C (12) 
                 2369  
                 (7) 
                  510 (30) 
                 −1988  
                 (9) 
                 70 (5) 
               
               
                 C (11) 
                 1770  
                 (7) 
                  150 (30) 
                 −2865  
                 (8) 
                 73 (5) 
               
               
                 C (15) 
                 1707  
                 (7) 
                 5230 (30) 
                 −1516  
                 (9) 
                 80 (5) 
               
               
                 C (6) 
                 −46  
                 (8) 
                 4130 (30) 
                 −4071 
                 (9) 
                 65 (5) 
               
               
                 C (26) 
                 5691  
                 (7) 
                 8780 (30) 
                 2800  
                 (9) 
                 88 (6) 
               
               
                 C (8) 
                 1030  
                 (7) 
                 2920 (30) 
                 −2802  
                 (8)  
                 66 (5) 
               
               
                 C (18) 
                 2523  
                 (7) 
                 4320 (30) 
                 −2154  
                 (8) 
                 73 (5) 
               
               
                 C (20) 
                 3602  
                 (7) 
                 3590 (30) 
                 −353 
                 (9) 
                 70 (5) 
               
               
                 C (3) 
                 −1896 
                 (7) 
                 5020 (30) 
                 −5628  
                 (9) 
                 72 (5) 
               
               
                 C (25) 
                 5644  
                 (8) 
                 7180 (30) 
                 2222  
                 (11) 
                 78 (5) 
               
               
                 C (7) 
                 531  
                 (8) 
                 4390 (30) 
                 −3271  
                 (10) 
                 70 (5) 
               
               
                 C (23) 
                 4709  
                 (7) 
                 4800 (30) 
                 1009 
                 (8) 
                 74 (5) 
               
               
                 C (22) 
                 3957 
                 (7) 
                 4050 (30) 
                 548  
                 (8) 
                 79 (5) 
               
               
                 C (21) 
                 3963 
                 (8) 
                 1690 (30) 
                 −441  
                 (10) 
                 105 (7)  
               
               
                 C (16) 
                 2465 
                 (7) 
                 5150 (30) 
                 −720  
                 (9) 
                 80 (5) 
               
               
                 C (24) 
                 4898  
                 (8) 
                 6230 (30) 
                 1673  
                 (11) 
                 79 (5) 
               
               
                   
               
             
          
         
       
     
     
       
         
               
             
               
               
               
             
           
               
                 TABLE 3 
               
               
                   
               
               
                 Bond lengths [Å] for F-24. 
               
               
                   
               
             
             
               
                   
               
             
          
           
               
                   
                 F(1)—C(24) 
                 1.397 (19) 
               
               
                   
                 F(2)—C(24) 
                 1.368 (17) 
               
               
                   
                 O(1)—C(1) 
                 1.441 (18) 
               
               
                   
                 O(1)—H(1A) 
                 0.8400 
               
               
                   
                 O(3)—C(3) 
                 1.392 (18) 
               
               
                   
                 O(3)—H(3A) 
                 0.8400 
               
               
                   
                 O(25)—C(25) 
                 1.420 (18) 
               
               
                   
                 O(25)—H(25A) 
                 0.8400 
               
               
                   
                 C(14)—C(8) 
                 1.479 (19) 
               
               
                   
                 C(14)—C(15) 
                 1.50 (2) 
               
               
                   
                 C(14)—C(13) 
                 1.577 (19) 
               
               
                   
                 C(14)—H(14A) 
                 1.0000 
               
               
                   
                 C(13)—C(18) 
                 1.49 (2) 
               
               
                   
                 C(13)—C(12) 
                 1.52 (2) 
               
               
                   
                 C(13)—C(17) 
                 1.553 (18) 
               
               
                   
                 C(4)—C(5) 
                 1.510 (18) 
               
               
                   
                 C(4)—C(3) 
                 1.525 (18) 
               
               
                   
                 C(4)—H(4A) 
                 0.9900 
               
               
                   
                 C(4)—H(4B) 
                 0.9900 
               
               
                   
                 C(10)—C(1) 
                 1.530 (19) 
               
               
                   
                 C(10)—C(5) 
                 1.60 (2) 
               
               
                   
                 C(10)—H(10A) 
                 0.9900 
               
               
                   
                 C(10)—H(10B) 
                 0.9990 
               
               
                   
                 C(5)—C(6) 
                 1.30 (2) 
               
               
                   
                 C(9)—C(11) 
                 1.513 (18) 
               
               
                   
                 C(9)—C(8) 
                 1.54 (2) 
               
               
                   
                 C(9)—H(9A) 
                 0.9900 
               
               
                   
                 C(9)—H(9B) 
                 0.9900 
               
               
                   
                 C(27)—C(25) 
                 1.53 (2) 
               
               
                   
                 C(27)—H(27A) 
                 0.9800 
               
               
                   
                 C(27)—H(27B) 
                 0.9800 
               
               
                   
                 C(27)—H(27C) 
                 0.9800 
               
               
                   
                 C(17)—C(20) 
                 1.498 (18) 
               
               
                   
                 C(17)—C(16) 
                 1.58 (2) 
               
               
                   
                 C(17)—H(17A) 
                 1.0000 
               
               
                   
                 C(1)—C(2) 
                 1.53 (2) 
               
               
                   
                 C(1)—H(1B) 
                 1.0000 
               
               
                   
                 C(2)—C(19) 
                 1.31 (2) 
               
               
                   
                 C(2)—C(3) 
                 1.55 (2) 
               
               
                   
                 C(19)—H(19A) 
                 0.9500 
               
               
                   
                 C(19)—H(19B) 
                 0.9500 
               
               
                   
                 C(12)—C(11)  
                 1.517 (17) 
               
               
                   
                 C(12)—H(12A) 
                 0.9900 
               
               
                   
                 C(12)—H(12B) 
                 0.9900 
               
               
                   
                 C(11)—H(11A) 
                 0.9900 
               
               
                   
                 C(11)—H(11B) 
                 0.9900 
               
               
                   
                 C(15)—C(16) 
                 1.562 (18) 
               
               
                   
                 C(15)—H(15A) 
                 0.9900 
               
               
                   
                 C(15)—H(15B) 
                 0.9900 
               
               
                   
                 C(6)—C(7) 
                 1.397 (18) 
               
               
                   
                 C(6)—H(6A) 
                 0.9500 
               
               
                   
                 C(26)—C(25) 
                 1.51 (2) 
               
               
                   
                 C(26)—H(26A) 
                 0.9800 
               
               
                   
                 C(26)—H(26B) 
                 0.9800 
               
               
                   
                 C(26)—H(26C) 
                 0.9800 
               
               
                   
                 C(8)—C(7) 
                 1.35 (2) 
               
               
                   
                 C(18)—H(18A) 
                 0.9800 
               
               
                   
                 C(18)—H(18B) 
                 0.9800 
               
               
                   
                 C(18)—H(18C) 
                 0.9800 
               
               
                   
                 C(20)—C(21) 
                 1.54 (2) 
               
               
                   
                 C(20)—C(22) 
                 1.550 (18) 
               
               
                   
                 C(20)—H(20A) 
                 1.0000 
               
               
                   
                 C(3)—H(3B) 
                 1.0000 
               
               
                   
                 C(25)—C(24) 
                 1.55 (2) 
               
               
                   
                 C(7)—H(7A) 
                 0.9500 
               
               
                   
                 C(23)—C(24) 
                 1.47 (2) 
               
               
                   
                 C(23)—C(22) 
                 1.519 (18) 
               
               
                   
                 C(23)—H(23A) 
                 0.9900 
               
               
                   
                 C(23)—H(23B) 
                 0.9900 
               
               
                   
                 C(22)—H(22A) 
                 0.9900 
               
               
                   
                 C(22)—H(22B) 
                 0.9900 
               
               
                   
                 C(21)—H(21A) 
                 0.9800 
               
               
                   
                 C(21)—H(21B) 
                 0.9800 
               
               
                   
                 C(21)—H(21C) 
                 0.9800 
               
               
                   
                 C(16)—H(16A) 
                 0.9900 
               
               
                   
                 C(16)—H(16B) 
                 0.9900 
               
               
                   
                   
               
             
          
         
       
     
     
       
         
               
             
               
               
               
             
           
               
                 TABLE 4 
               
               
                   
               
               
                 bond angles [°] for F-24. 
               
               
                   
               
             
             
               
                   
               
             
          
           
               
                   
                 C(1)—O(1)—H(1A) 
                 109.5 
               
               
                   
                 C(3)—O(3)—H(3A) 
                 109.5 
               
               
                   
                 C(25)—O(25)—H(25A) 
                 109.5 
               
               
                   
                 C(8)—C(14)—C(15) 
                 120.2 (14) 
               
               
                   
                 C(8)—C(14)—C(13) 
                 115.3 (12) 
               
               
                   
                 C(15)—C(14)—C(13) 
                 104.0 (12) 
               
               
                   
                 C(8)—C(14)—H(14A) 
                 105.4 
               
               
                   
                 C(15)—C(14)—H(14A) 
                 105.4 
               
               
                   
                 C(13)—C(14)—H(14A) 
                 105.4 
               
               
                   
                 C(18)—C(13)—C(12) 
                 110.5 (12) 
               
               
                   
                 C(18)—C(13)—C(17) 
                 110.9 (13) 
               
               
                   
                 C(12)—C(13)—C(17) 
                 116.3 (13) 
               
               
                   
                 C(18)—C(13)—C(14) 
                 111.3 (13) 
               
               
                   
                 C(12)—C(13)—C(14) 
                 107.1 (12) 
               
               
                   
                 C(17)—C(13)—C(14) 
                 100.3 (11) 
               
               
                   
                 C(5)—C(4)—C(3) 
                 115.1 (12) 
               
               
                   
                 C(5)—C(4)—H(4A) 
                 108.5 
               
               
                   
                 C(3)—C(4)—H(4A) 
                 108.5 
               
               
                   
                 C(5)—C(4)—H(4B) 
                 108.5 
               
               
                   
                 C(3)—C(4)—H(4B) 
                 108.5 
               
               
                   
                 H(4A)—C(4)—H(4B) 
                 107.5 
               
               
                   
                 C(1)—C(10)—C(5) 
                 108.1 (13) 
               
               
                   
                 C(1)—C(10)—H(10A) 
                 110.1 
               
               
                   
                 C(5)—C(10)—H(10A) 
                 110.1 
               
               
                   
                 C(1)—C(10)—H(10B) 
                 110.1 
               
               
                   
                 C(5)—C(10)—H(10B) 
                 110.1 
               
               
                   
                 H(10A)—C(10)—H(10B) 
                 108.4 
               
               
                   
                 C(6)—C(5)—C(4) 
                 124.7 (18) 
               
               
                   
                 C(6)—C(5)—C(10) 
                 123.1 (14) 
               
               
                   
                 C(4)—C(5)—C(10) 
                 112.2 (15) 
               
               
                   
                 C(11)—C(9)—C(8) 
                 112.2 (13) 
               
               
                   
                 C(11)—C(9)—H(9A) 
                 109.2 
               
               
                   
                 C(8)—C(9)—H(9A) 
                 109.2 
               
               
                   
                 C(11)—C(9)—H(9B) 
                 109.2 
               
               
                   
                 C(8)—C(9)—H(9B) 
                 109.2 
               
               
                   
                 H(9A)—C(9)—H(9B) 
                 107.9 
               
               
                   
                 C(25)—C(27)—H(27A) 
                 109.5 
               
               
                   
                 C(25)—C(27)—H(27B) 
                 109.5 
               
               
                   
                 H(27A)—C(27)—H(27B) 
                 109.5 
               
               
                   
                 C(25)—C(27)—H(27C) 
                 109.5 
               
               
                   
                 H(27A)—C(27)—H(27C) 
                 109.5 
               
               
                   
                 H(27B)—C(27)—H(27C) 
                 109.5 
               
               
                   
                 C(20)—C(17)—C(13) 
                 121.4 (12) 
               
               
                   
                 C(20)—C(17)—C(16) 
                 111.1 (13) 
               
               
                   
                 C(13)—C(17)—C(16) 
                 104.0 (12) 
               
               
                   
                 C(20)—C(17)—H(17A) 
                 106.5 
               
               
                   
                 C(13)—C(17)—H(17A) 
                 106.5 
               
               
                   
                 C(16)—C(17)—H(17A) 
                 106.5 
               
               
                   
                 O(1)—C(1)—C(2) 
                 111.7 (13) 
               
               
                   
                 O(1)—C(1)—C(10) 
                 111.5 (12) 
               
               
                   
                 C(2)—C(1)—C(10) 
                 110.4 (13) 
               
               
                   
                 O(1)—C(1)—H(1B) 
                 107.7 
               
               
                   
                 C(2)—C(1)—H(1B) 
                 107.7 
               
               
                   
                 C(10)—C(1)—H(1B) 
                 107.7 
               
               
                   
                 C(19)—C(2)—C(1) 
                 126.8 (17) 
               
               
                   
                 C(19)—C(2)—C(3) 
                 123.4 (16) 
               
               
                   
                 C(1)—C(2)—C(3) 
                 109.8 (15) 
               
               
                   
                 C(2)—C(19)—H(19A) 
                 120.0 
               
               
                   
                 C(2)—C(19)—H(19B) 
                 120.0 
               
               
                   
                 H(19A)—C(19)—H(19B) 
                 120.0 
               
               
                   
                 C(13)—C(12)—C(11) 
                 111.2 (12) 
               
               
                   
                 C(13)—C(12)—H(12A) 
                 109.4 
               
               
                   
                 C(11)—C(12)—H(12A) 
                 109.4 
               
               
                   
                 C(13)—C(12)—H(12B) 
                 109.4 
               
               
                   
                 C(11)—C(12)—H(12B) 
                 109.4 
               
               
                   
                 H(12A)—C(12)—H(12B) 
                 108.0 
               
               
                   
                 C(9)—C(11)—C(12) 
                 114.6 (13) 
               
               
                   
                 C(9)—C(11)—H(11A) 
                 108.6 
               
               
                   
                 C(12)—C(11)—H(11A) 
                 108.6 
               
               
                   
                 C(9)—C(11)—H(11B) 
                 108.6 
               
               
                   
                 C(12)—C(11)—H(11B) 
                 108.6 
               
               
                   
                 H(11A)—C(11)—H(11B) 
                 107.6 
               
               
                   
                 C(14)—C(15)—C(16) 
                 105.3 (13) 
               
               
                   
                 C(14)—C(15)—H(15A) 
                 110.7 
               
               
                   
                 C(16)—C(15)—H(15A) 
                 110.7 
               
               
                   
                 C(14)—C(15)—H(15B) 
                 110.7 
               
               
                   
                 C(16)—C(15)—H(15B) 
                 110.7 
               
               
                   
                 H(15A)—C(15)—H(15B) 
                 108.8 
               
               
                   
                 C(5)—C(6)—C(7) 
                 131.2 (17) 
               
               
                   
                 C(5)—C(6)—H(6A) 
                 114.4 
               
               
                   
                 C(7)—C(6)—H(6A) 
                 114.4 
               
               
                   
                 C(25)—C(26)—H(26A) 
                 109.5 
               
               
                   
                 C(25)—C(26)—H(26B) 
                 109.5 
               
               
                   
                 H(26A)—C(26)—H(26B) 
                 109.5 
               
               
                   
                 C(25)—C(26)—H(26B) 
                 109.5 
               
               
                   
                 H(26A)—C(26)—H(26C) 
                 109.5 
               
               
                   
                 H(26B)—C(26)—H(26C) 
                 109.5 
               
               
                   
                 C(7)—C(8)—C(14) 
                 126.0 (17) 
               
               
                   
                 C(7)—C(8)—C(9) 
                 124.5 (13) 
               
               
                   
                 C(14)—C(8)—C(9) 
                 109.5 (14) 
               
               
                   
                 C(13)—C(18)—H(18A) 
                 109.5 
               
               
                   
                 C(13)—C(18)—H(18B) 
                 109.5 
               
               
                   
                 H(18A)—C(18)—H(18B) 
                 109.5 
               
               
                   
                 C(13)—C(18)—H(18C) 
                 109.5 
               
               
                   
                 H(18A)—C(18)—H(18C) 
                 109.5 
               
               
                   
                 H(18B)—C(18)—H(18C) 
                 109.5 
               
               
                   
                 C(17)—C(20)—C(21) 
                 111.2 (13) 
               
               
                   
                 C(17)—C(20)—C(22) 
                 112.4 (12) 
               
               
                   
                 C(21)—C(20)—C(22) 
                 110.0 (13) 
               
               
                   
                 C(17)—C(20)—H(20A) 
                 107.7 
               
               
                   
                 C(21)—C(20)—H(20A) 
                 107.7 
               
               
                   
                 C(22)—C(20)—H(20A) 
                 107.7 
               
               
                   
                 O(3)—C(3)—C(4) 
                 110.8 (13) 
               
               
                   
                 O(3)—C(3)—C(2) 
                 110.5 (13) 
               
               
                   
                 C(4)—C(3)—C(2) 
                 105.5 (14) 
               
               
                   
                 O(3)—C(3)—H(3B) 
                 110.0 
               
               
                   
                 C(4)—C(3)—H(3B) 
                 110.0 
               
               
                   
                 C(2)—C(3)—H(3B) 
                 110.0 
               
               
                   
                 O(25)—C(25)—C(26) 
                 112.2 (14) 
               
               
                   
                 O(25)—C(25)—C(27) 
                 106.0 (14) 
               
               
                   
                 C(26)—C(25)—C(27) 
                 112.3 (15) 
               
               
                   
                 O(25)—C(25)—C(24) 
                 106.3 (14) 
               
               
                   
                 C(26)—C(25)—C(24) 
                 110.3 (14) 
               
               
                   
                 C(27)—C(25)—C(24) 
                 109.5 (14) 
               
               
                   
                 C(8)—C(7)—C(6) 
                 126.5 (16) 
               
               
                   
                 C(8)—C(7)—H(7A) 
                 116.8 
               
               
                   
                 C(6)—C(7)—H(7A) 
                 116.8 
               
               
                   
                 C(24)—C(23)—C(22) 
                 111.6 (12) 
               
               
                   
                 C(24)—C(23)—H(23A) 
                 109.3 
               
               
                   
                 C(22)—C(23)—H(23A) 
                 109.3 
               
               
                   
                 C(24)—C(23)—H(23B) 
                 109.3 
               
               
                   
                 C(22)—C(23)—H(23B) 
                 109.3 
               
               
                   
                 H(23A)—C(23)—H(23B) 
                 108.0 
               
               
                   
                 C(23)—C(22)—C(20) 
                 114.2 (12) 
               
               
                   
                 C(23)—C(22)—H(22A) 
                 108.7 
               
               
                   
                 C(20)—C(22)—H(22A) 
                 108.7 
               
               
                   
                 C(23)—C(22)—H(22B) 
                 108.7 
               
               
                   
                 C(20)—C(22)—H(22B) 
                 108.7 
               
               
                   
                 H(22A)—C(22)—H(22B) 
                 107.6 
               
               
                   
                 C(20)—C(21)—H(21A) 
                 109.5 
               
               
                   
                 C(20)—C(21)—H(21B) 
                 109.5 
               
               
                   
                 H(21A)—C(21)—H(21B) 
                 109.5 
               
               
                   
                 C(20)—C(21)—H(21B) 
                 109.5 
               
               
                   
                 H(21A)—C(21)—H(21C) 
                 109.5 
               
               
                   
                 H(21B)—C(21)—H(21C) 
                 109.5 
               
               
                   
                 C(15)—C(16)—C(17) 
                 105.7 (12) 
               
               
                   
                 C(15)—C(16)—H(16A) 
                 110.6 
               
               
                   
                 C(17)—C(16)—H(16A) 
                 110.6 
               
               
                   
                 C(15)—C(16)—H(16B) 
                 110.6 
               
               
                   
                 C(17)—C(16)—H(16B) 
                 110.6 
               
               
                   
                 H(16A)—C(16)—H(16B) 
                 108.7 
               
               
                   
                 F(2)—C(24)—F(1) 
                 103.0 (13) 
               
               
                   
                 F(2)—C(24)—C(23) 
                 110.8 (15) 
               
               
                   
                 F(1)—C(24)—C(23) 
                 108.4 (13) 
               
               
                   
                 F(2)—C(24)—C(25) 
                 107.3 (14) 
               
               
                   
                 F(1)—C(24)—C(25) 
                 106.0 (15) 
               
               
                   
                 C(23)—C(24)—C(25) 
                 119.9 (14) 
               
               
                   
                   
               
             
          
         
       
     
     
       
         
               
             
               
               
               
               
               
               
               
             
               
               
               
               
               
               
               
               
               
               
               
               
               
             
           
               
                 TABLE 5 
               
             
             
               
                   
               
               
                 Anisotropic displacement parameters (Å 2  × 10 3 ) for F-24. The anisotropic 
               
               
                 displacement factor exponent takes the form ″−2π 2 [h 2 a*2U 11  + +2hka*b*U 12 ] 
               
             
          
           
               
                   
                 U11 
                 U22 
                 U33 
                 U23 
                 U13 
                 U12 
               
               
                   
                   
               
             
          
           
               
                 F(1) 
                 80 
                 (6) 
                 86 
                 (9) 
                 104 
                 (7) 
                 4 
                 (6) 
                 47 
                 (5) 
                 17 
                 (6) 
               
               
                 F(2) 
                 91 
                 (6) 
                 97 
                 (9) 
                 88 
                 (6) 
                 −16 
                 (6) 
                 57 
                 (5) 
                 −22 
                 (6) 
               
               
                 O(1) 
                 88 
                 (7) 
                 53 
                 (10) 
                 76 
                 (6) 
                 −5 
                 (6) 
                 41 
                 (6) 
                 1 
                 (6) 
               
               
                 O(3) 
                 96 
                 (8) 
                 56 
                 (9) 
                 101 
                 (8) 
                 8 
                 (7) 
                 60 
                 (7) 
                 −8 
                 (7) 
               
               
                 O(25) 
                 76 
                 (6) 
                 76 
                 (9) 
                 89 
                 (7) 
                 1 
                 (7) 
                 47 
                 (5) 
                 −3 
                 (7) 
               
               
                 C(14) 
                 88 
                 (11) 
                 5 
                 (10) 
                 90 
                 (11) 
                 −11 
                 (9) 
                 50 
                 (9) 
                 −10 
                 (8) 
               
               
                 C(13) 
                 63 
                 (10) 
                 56 
                 (15) 
                 68 
                 (10) 
                 −1 
                 (10) 
                 45 
                 (9) 
                 −11 
                 (9) 
               
               
                 C(4) 
                 76 
                 (10) 
                 61 
                 (15) 
                 91 
                 (12) 
                 23 
                 (11) 
                 52 
                 (10) 
                 25 
                 (10) 
               
               
                 C(10) 
                 79 
                 (12) 
                 52 
                 (15) 
                 72 
                 (9) 
                 −3 
                 (10) 
                 38 
                 (9) 
                 −5 
                 (9) 
               
               
                 C(5) 
                 52 
                 (10) 
                 78 
                 (15) 
                 74 
                 (11) 
                 −2 
                 (11) 
                 36 
                 (9) 
                 −22 
                 (11) 
               
               
                 C(9) 
                 68 
                 (10) 
                 36 
                 (13) 
                 88 
                 (10) 
                 −15 
                 (10) 
                 39 
                 (8) 
                 −10 
                 (9) 
               
               
                 C(27) 
                 73 
                 (10) 
                 97 
                 (17) 
                 86 
                 (11) 
                 26 
                 (12) 
                 42 
                 (9) 
                 8 
                 (11) 
               
               
                 C(17) 
                 84 
                 (11) 
                 42 
                 (12) 
                 84 
                 (11) 
                 4 
                 (9) 
                 57 
                 (10) 
                 11 
                 (9) 
               
               
                 C(1) 
                 84 
                 (12) 
                 13 
                 (12) 
                 94 
                 (12) 
                 −18 
                 (9) 
                 46 
                 (10) 
                 −16 
                 (9) 
               
               
                 C(2) 
                 64 
                 (11) 
                 54 
                 (16) 
                 75 
                 (13) 
                 0 
                 (11) 
                 32 
                 (11) 
                 −12 
                 (9) 
               
               
                 C(19) 
                 83 
                 (11) 
                 80 
                 (17) 
                 85 
                 (12) 
                 −12 
                 (12) 
                 54 
                 (10) 
                 −10 
                 (12) 
               
               
                 C(12) 
                 79 
                 (10) 
                 32 
                 (13) 
                 94 
                 (12) 
                 13 
                 (10) 
                 49 
                 (10) 
                 13 
                 (9) 
               
               
                 C(11) 
                 79 
                 (10) 
                 33 
                 (12) 
                 85 
                 (11) 
                 −18 
                 (9) 
                 36 
                 (9) 
                 −6 
                 (9) 
               
               
                 C(15) 
                 79 
                 (11) 
                 49 
                 (14) 
                 115 
                 (12) 
                 6 
                 (12) 
                 59 
                 (10) 
                 6 
                 (10) 
               
               
                 C(6) 
                 50 
                 (9) 
                 61 
                 (13) 
                 74 
                 (11) 
                 4 
                 (9) 
                 31 
                 (9) 
                 8 
                 (9) 
               
               
                 C(26) 
                 82 
                 (11) 
                 76 
                 (15) 
                 98 
                 (12) 
                 −8 
                 (11) 
                 50 
                 (10) 
                 −7 
                 (10) 
               
               
                 C(8) 
                 59 
                 (10) 
                 67 
                 (15) 
                 58 
                 (10) 
                 −11 
                 (10) 
                 28 
                 (9) 
                 −13 
                 (10) 
               
               
                 C(18) 
                 99 
                 (11) 
                 52 
                 (13) 
                 84 
                 (10) 
                 −1 
                 (9) 
                 64 
                 (10) 
                 −15 
                 (9) 
               
               
                 C(20) 
                 58 
                 (10) 
                 44 
                 (13) 
                 92 
                 (12) 
                 −1 
                 (10) 
                 36 
                 (9) 
                 13 
                 (9) 
               
               
                 C(3) 
                 74 
                 (11) 
                 58 
                 (16) 
                 73 
                 (10) 
                 −15 
                 (11) 
                 37 
                 (9) 
                 −4 
                 (10) 
               
               
                 C(25) 
                 77 
                 (13) 
                 44 
                 (15) 
                 98 
                 (13) 
                 14 
                 (11) 
                 45 
                 (11) 
                 24 
                 (10) 
               
               
                 C(7) 
                 66 
                 (10) 
                 48 
                 (12) 
                 78 
                 (11) 
                 19 
                 (10) 
                 33 
                 (10) 
                 10 
                 (10) 
               
               
                 C(23) 
                 89 
                 (12) 
                 61 
                 (14) 
                 73 
                 (10) 
                 −20 
                 (10) 
                 48 
                 (9) 
                 −3 
                 (10) 
               
               
                 C(22) 
                 76 
                 (11) 
                 79 
                 (14) 
                 77 
                 (11) 
                 −6 
                 (10) 
                 43 
                 (9) 
                 −6 
                 (10) 
               
               
                 C(21) 
                 78 
                 (12) 
                 110 
                 (19) 
                 99 
                 (12) 
                 −15 
                 (12) 
                 37 
                 (10) 
                 −8 
                 (12) 
               
               
                 C(16) 
                 94 
                 (12) 
                 52 
                 (13) 
                 107 
                 (12) 
                 −33 
                 (11) 
                 67 
                 (11) 
                 −13 
                 (11) 
               
               
                 C(24) 
                 66 
                 (12) 
                 88 
                 (17) 
                 91 
                 (13) 
                 14 
                 (13) 
                 52 
                 (11) 
                 12 
                 (11) 
               
               
                   
               
             
          
         
       
     
     
       
         
               
             
               
               
               
               
               
             
               
               
               
               
               
             
           
               
                 TABLE 6 
               
             
             
               
                   
               
               
                 Hydrogen coordinates (Å 2  × 10 4 ) and isotropic displacement  
               
               
                 parameters (Å 2  × 10 3 ) for F-24. 
               
             
          
           
               
                   
                 x 
                 y 
                 z 
                 U (eq) 
               
               
                   
               
             
          
           
               
                 H (1A) 
                 −1670 
                 10649 
                 −4627 
                 115 
               
               
                 H (3A) 
                 −2379 
                 3772 
                 −5284 
                 125 
               
               
                 H (25A) 
                 6210 
                 5340 
                 3093 
                 123 
               
               
                 H (14A) 
                 1558 
                 2057 
                 −1654 
                 76 
               
               
                 H (4A) 
                 −1099 
                 3363 
                 −5526 
                 89 
               
               
                 H (4B) 
                 −1132 
                 5802 
                 −5767 
                 89 
               
               
                 H (10A) 
                 −337 
                 7817 
                 −3695 
                 86 
               
               
                 H (10B) 
                 −610 
                 8789 
                 −4554 
                 86 
               
               
                 H (9A) 
                 931 
                 −389 
                 −2838 
                 83 
               
               
                 H (9B) 
                 707 
                 584 
                 −3675 
                 83 
               
               
                 H (27A) 
                 6307 
                 8780 
                 2048 
                 133 
               
               
                 H (27B) 
                 5501 
                 9273 
                 1358 
                 133 
               
               
                 H (27C) 
                 5832 
                 7048 
                 1364 
                 133 
               
               
                 H (17A) 
                 2777 
                 1957 
                 −560 
                 79 
               
               
                 H (1B) 
                 −1473 
                 6556 
                 −4233 
                 81 
               
               
                 H (19A) 
                 −2411 
                 10144 
                 −5804 
                 96 
               
               
                 H (19B) 
                 −2711 
                 8324 
                 −6509 
                 96 
               
               
                 H (12A) 
                 2328 
                 −498 
                 −1651 
                 84 
               
               
                 H (12B) 
                 2817 
                 232 
                 −1904 
                 84 
               
               
                 H (11A) 
                 1850 
                 1033 
                 −3200 
                 88 
               
               
                 H (11B) 
                 1774 
                 −1359 
                 −2999 
                 88 
               
               
                 H (15A) 
                 1361 
                 5317 
                 −1400 
                 96 
               
               
                 H (15B) 
                 1647 
                 6473 
                 −1846 
                 96 
               
               
                 H (6A) 
                 −50 
                 2820 
                 −4306 
                 79 
               
               
                 H (26A) 
                 5565 
                 8086 
                 3121 
                 132 
               
               
                 H (26B) 
                 5370 
                 9964 
                 2496 
                 132 
               
               
                 H (26C) 
                 6169 
                 9327 
                 3156 
                 132 
               
               
                 H (18A) 
                 2989 
                 4030 
                 −2009 
                 109 
               
               
                 H (18B) 
                 2508 
                 5774 
                 −1994 
                 109 
               
               
                 H (18C) 
                 2176 
                 4166 
                 −2736 
                 109 
               
               
                 H (20A) 
                 3668 
                 4870 
                 −588 
                 83 
               
               
                 H (3B) 
                 −2254 
                 4751 
                 −6215 
                 86 
               
               
                 H (7A) 
                 578 
                 5736 
                 −3033 
                 85 
               
               
                 H (23A) 
                 5023 
                 3547 
                 1228 
                 89 
               
               
                 H (23B) 
                 4774 
                 5551 
                 638 
                 89 
               
               
                 H (22A) 
                 3684 
                 5148 
                 591 
                 95 
               
               
                 H (22B) 
                 3946 
                 2733 
                 804 
                 95 
               
               
                 H (21A) 
                 3749 
                 1454 
                 −1011 
                 158 
               
               
                 H (21B) 
                 3909 
                 413 
                 −211 
                 158 
               
               
                 H (21C) 
                 4460 
                 2010 
                 −155 
                 158 
               
               
                 H (16A)  
                 2456 
                 4936 
                 −253 
                 96 
               
               
                 H (16B) 
                 2715 
                 6497 
                 −643 
                 96 
               
               
                   
               
             
          
         
       
     
     
       
         
               
             
               
               
               
               
             
           
               
                 TABLE 7 
               
               
                   
               
               
                 Torsion angles [deg] for F-24. 
               
               
                   
               
             
             
               
                   
               
             
          
           
               
                   
                 C(8)—C(14)—C(13)—C(18) 
                 62.3  
                 (18) 
               
               
                   
                 C(15)—C(14)—C(13)—C(18) 
                 −71.4  
                 (15) 
               
               
                   
                 C(8)—C(14)—C(13)—C(12) 
                 −58.5  
                 (17) 
               
               
                   
                 C(15)—C(14)—C(13)—C(12) 
                 167.8 
                 (12) 
               
               
                   
                 C(8)—C(14)—C(13)—C(17) 
                 179.7  
                 (14) 
               
               
                   
                 C(15)—C(14)—C(13)—C(17) 
                 45.9  
                 (15) 
               
               
                   
                 C(3)—C(4)—C(5)—C(6) 
                 127.4  
                 (17) 
               
               
                   
                 C(3)—C(4)—C(5)—C(10) 
                 −52.6  
                 (19) 
               
               
                   
                 C(1)—C(10)—C(5)—C(6) 
                 −130.4  
                 (15) 
               
               
                   
                 C(1)—C(10)—C(5)—C(4) 
                 49.7 
                 (15) 
               
               
                   
                 C(18)—C(13)—C(17)—C(20) 
                 −46 
                 (2) 
               
               
                   
                 C(12)—C(13)—C(17)—C(20) 
                 81.1  
                 (19) 
               
               
                   
                 C(14)—C(13)—C(17)—C(20) 
                 −163.9  
                 (14) 
               
               
                   
                 C(18)—C(13)—C(17)—C(16) 
                 79.6  
                 (14) 
               
               
                   
                 C(12)—C(13)—C(17)—C(16) 
                 −153.1  
                 (13) 
               
               
                   
                 C(14)—C(13)—C(17)—C(16) 
                 −38.0  
                 (14) 
               
               
                   
                 C(5)—C(10)—C(1)—O(1) 
                 178.2  
                 (11) 
               
               
                   
                 C(5)—C(10)—C(1)—C(2) 
                 −57.1  
                 (17) 
               
               
                   
                 O(1)—C(1)—C(2)—C(19) 
                 12  
                 (2) 
               
               
                   
                 C(10)—C(1)—C(2)—C(19) 
                 −112.3 
                 (19) 
               
               
                   
                 O(1)—C(1)—C(2)—C(3) 
                 −168.5  
                 (13) 
               
               
                   
                 C(10)—C(1)—C(2)—C(3) 
                 66.9  
                 (17) 
               
               
                   
                 C(18)—C(13)—C(12)—C(11) 
                 −66.7  
                 (16) 
               
               
                   
                 C(17)—C(13)—C(12)—C(11) 
                 165.8  
                 (12) 
               
               
                   
                 C(14)—C(13)—C(12)—C(11) 
                 54.6 
                 (15) 
               
               
                   
                 C(8)—C(9)—C(11)—C(12) 
                 51 
                 (2) 
               
               
                   
                 C(13)—C(12)—C(11)—C(9) 
                 −55.1  
                 (19) 
               
               
                   
                 C(8)—C(14)—C(15)—C(16) 
                 −166.0  
                 (13) 
               
               
                   
                 C(13)—C(14)—C(15)—C(16) 
                 −35.1  
                 (15) 
               
               
                   
                 C(4)—C(5)—C(6)—C(7) 
                 179.7 
                 (14) 
               
               
                   
                 C(10)—C(5)—C(6)—C(7) 
                 0  
                 (3) 
               
               
                   
                 C(15)—C(14)—C(8)—C(7) 
                 0  
                 (2) 
               
               
                   
                 C(13)—C(14)—C(8)—C(7) 
                 −125.3 
                 (16) 
               
               
                   
                 C(15)—C(14)—C(8)—C(9) 
                 −178.6  
                 (13) 
               
               
                   
                 C(13)—C(14)—C(8)—C(9) 
                 55.6  
                 (17) 
               
               
                   
                 C(11)—C(9)—C(8)—C(7) 
                 130.9 
                 (16) 
               
               
                   
                 C(11)—C(9)—C(8)—C(14) 
                 −50.0  
                 (17) 
               
               
                   
                 C(13)—C(17)—C(20)—C(21) 
                 −58 
                 (2) 
               
               
                   
                 C(16)—C(17)—C(20)—C(21) 
                 179.7  
                 (13) 
               
               
                   
                 C(13)—C(17)—C(20)—C(22) 
                 178.5  
                 (15) 
               
               
                   
                 C(16)—C(17)—C(20)—C(22) 
                 55.9 
                 (18) 
               
               
                   
                 C(5)—C(4)—C(3)—O(3) 
                 −62 
                 (2) 
               
               
                   
                 C(5)—C(4)—C(3)—C(2) 
                 57 
                 (2) 
               
               
                   
                 C(19)—C(2)—C(3)—O(3) 
                 −124.0  
                 (17) 
               
               
                   
                 C(1)—C(2)—C(3)—O(3)  
                 56.8  
                 (15) 
               
               
                   
                 C(19)—C(2)—C(3)—C(4) 
                 116.2 
                 (16) 
               
               
                   
                 C(1)—C(2)—C(3)—C(4) 
                 −63.0  
                 (17) 
               
               
                   
                 C(14)—C(8)—C(7)—C(6) 
                 −177.1  
                 (14) 
               
               
                   
                 C(9)—C(8)—C(7)—C(6)  
                 2  
                 (2) 
               
               
                   
                 C(5)—C(6)—C(7)—C(8) 
                 173.8  
                 (17) 
               
               
                   
                 C(24)—C(23)—C(22)—C(20) 
                 149.6 
                 (15) 
               
               
                   
                 C(17)—C(20)—C(22)—C(23) 
                 −170.3  
                 (14) 
               
               
                   
                 C(21)—C(20)—C(22)—C(23) 
                 65.2  
                 (19) 
               
               
                   
                 C(14)—C(15)—C(16)—C(17) 
                 10.7  
                 (16) 
               
               
                   
                 C(20)—C(17)—C(16)—C(15) 
                 150.1  
                 (13) 
               
               
                   
                 C(13)—C(17)—C(16)—C(15) 
                 18.0  
                 (15) 
               
               
                   
                 C(22)—C(23)—C(24)—F(2) 
                 54.0 
                 (18) 
               
               
                   
                 C(22)—C(23)—C(24)—F(1) 
                 −58.4  
                 (18) 
               
               
                   
                 C(22)—C(23)—C(24)—C(25) 
                 179.9 
                 (16) 
               
               
                   
                 O(25)—C(25)—C(24)—F(2) 
                 63.3 
                 (18) 
               
               
                   
                 C(26)—C(25)—C(24)—F(2) 
                 −58.5  
                 (18) 
               
               
                   
                 C(27)—C(25)—C(24)—F(2) 
                 177.4  
                 (15) 
               
               
                   
                 O(25)—C(25)—C(24)—F(1) 
                 172.9 
                 (14) 
               
               
                   
                 C(26)—C(25)—C(24)—F(1) 
                 51.1  
                 (18) 
               
               
                   
                 C(27)—C(25)—C(24)—F(1) 
                 −73.0  
                 (17) 
               
               
                   
                 O(25)—C(25)—C(24)—C(23)  
                 −64  
                 (2) 
               
               
                   
                 C(26)—C(25)—C(24)—C(23) 
                 174.0  
                 (16) 
               
               
                   
                 C(27)—C(25)—C(24)—C(23) 
                 50 
                 (2) 
               
               
                   
                   
               
             
          
         
       
     
     
       
         
               
             
               
               
               
               
               
               
               
             
               
               
               
               
               
               
               
             
           
               
                 TABLE 8 
               
             
             
               
                   
               
               
                 Observed and calculated structure factors for F-24. 
               
             
          
           
               
                   
                 h 
                 k 
                 l 
                 10Fo 
                 10Fc 
                 10s 
               
               
                   
                   
               
             
          
           
               
                   
                 2 
                 0 
                 0 
                 150 
                 131 
                 18 
               
               
                   
                 4 
                 0 
                 0 
                 0 
                 6 
                 1 
               
               
                   
                 6 
                 0 
                 0 
                 659 
                 675 
                 24 
               
               
                   
                 8 
                 0 
                 0 
                 186 
                 166 
                 12 
               
               
                   
                 10 
                 0 
                 0 
                 135 
                 143 
                 18 
               
               
                   
                 12 
                 0 
                 0 
                 116 
                 147 
                 21 
               
               
                   
                 14 
                 0 
                 0 
                 155 
                 138 
                 19 
               
               
                   
                 16 
                 0 
                 0 
                 162 
                 165 
                 32 
               
               
                   
                 18 
                 0 
                 0 
                 116 
                 101 
                 45 
               
               
                   
                 1 
                 1 
                 0 
                 759 
                 770 
                 36 
               
               
                   
                 3 
                 1 
                 0 
                 604 
                 662 
                 29 
               
               
                   
                 5 
                 1 
                 0 
                 0 
                 40 
                 1 
               
               
                   
                 7 
                 1 
                 0 
                 631 
                 680 
                 17 
               
               
                   
                 9 
                 1 
                 0 
                 417 
                 591 
                 11 
               
               
                   
                 11 
                 1 
                 0 
                 143 
                 142 
                 14 
               
               
                   
                 13 
                 1 
                 0 
                 14 
                 96 
                 14 
               
               
                   
                 15 
                 1 
                 0 
                 149 
                 202 
                 14 
               
               
                   
                 17 
                 1 
                 0 
                 179 
                 154 
                 17 
               
               
                   
                 0 
                 2 
                 0 
                 1468 
                 1367 
                 78 
               
               
                   
                 2 
                 2 
                 0 
                 369 
                 323 
                 11 
               
               
                   
                 4 
                 2 
                 0 
                 278 
                 249 
                 8 
               
               
                   
                 6 
                 2 
                 0 
                 377 
                 352 
                 11 
               
               
                   
                 8 
                 2 
                 0 
                 439 
                 426 
                 13 
               
               
                   
                 10 
                 2 
                 0 
                 165 
                 158 
                 11 
               
               
                   
                 12 
                 2 
                 0 
                 72 
                 35 
                 40 
               
               
                   
                 14 
                 2 
                 0 
                 366 
                 324 
                 14 
               
               
                   
                 16 
                 2 
                 0 
                 0 
                 25 
                 1 
               
               
                   
                 1 
                 3 
                 0 
                 586 
                 509 
                 25 
               
               
                   
                 3 
                 3 
                 0 
                 126 
                 112 
                 12 
               
               
                   
                 5 
                 3 
                 0 
                 210 
                 203 
                 11 
               
               
                   
                 7 
                 3 
                 0 
                 81 
                 72 
                 24 
               
               
                   
                 9 
                 3 
                 0 
                 194 
                 180 
                 11 
               
               
                   
                 11 
                 3 
                 0 
                 129 
                 137 
                 19 
               
               
                   
                 13 
                 3 
                 0 
                 118 
                 99 
                 29 
               
               
                   
                 15 
                 3 
                 0 
                 138 
                 161 
                 25 
               
               
                   
                 0 
                 4 
                 0 
                 985 
                 699 
                 72 
               
               
                   
                 2 
                 4 
                 0 
                 110 
                 133 
                 31 
               
               
                   
                 4 
                 4 
                 0 
                 84 
                 125 
                 40 
               
               
                   
                 6 
                 4 
                 0 
                 88 
                 93 
                 26 
               
               
                   
                 8 
                 4 
                 0 
                 110 
                 102 
                 24 
               
               
                   
                 10 
                 4 
                 0 
                 115 
                 128 
                 25 
               
               
                   
                 12 
                 4 
                 0 
                 0 
                 23 
                 1 
               
               
                   
                 14 
                 4 
                 0 
                 0 
                 94 
                 1 
               
               
                   
                 1 
                 5 
                 0 
                 0 
                 26 
                 1 
               
               
                   
                 3 
                 5 
                 0 
                 139 
                 142 
                 63 
               
               
                   
                 5 
                 5 
                 0 
                 95 
                 160 
                 94 
               
               
                   
                 7 
                 5 
                 0 
                 111 
                 59 
                 110 
               
               
                   
                 9 
                 5 
                 0 
                 169 
                 172 
                 48 
               
               
                   
                 −18 
                 0 
                 1 
                 71 
                 45 
                 70 
               
               
                   
                 −16 
                 0 
                 1 
                 0 
                 32 
                 1 
               
               
                   
                 −14 
                 0 
                 1 
                 257 
                 274 
                 15 
               
               
                   
                 −12 
                 0 
                 1 
                 210 
                 209 
                 14 
               
               
                   
                 −10 
                 0 
                 1 
                 360 
                 389 
                 14 
               
               
                   
                 −8 
                 0 
                 1 
                 137 
                 139 
                 14 
               
               
                   
                 −6 
                 0 
                 1 
                 1186 
                 1185 
                 57 
               
               
                   
                 −4 
                 0 
                 1 
                 900 
                 906 
                 64 
               
               
                   
                 −2 
                 0 
                 1 
                 243 
                 242 
                 18 
               
               
                   
                 0 
                 0 
                 1 
                 272 
                 292 
                 20 
               
               
                   
                 2 
                 0 
                 1 
                 688 
                 663 
                 44 
               
               
                   
                 4 
                 0 
                 1 
                 175 
                 201 
                 33 
               
               
                   
                 6 
                 0 
                 1 
                 109 
                 106 
                 18 
               
               
                   
                 8 
                 0 
                 1 
                 782 
                 767 
                 29 
               
               
                   
                 10 
                 0 
                 1 
                 24 
                 42 
                 24 
               
               
                   
                 12 
                 0 
                 1 
                 239 
                 273 
                 14 
               
               
                   
                 14 
                 0 
                 1 
                 74 
                 29 
                 73 
               
               
                   
                 16 
                 0 
                 1 
                 337 
                 318 
                 24 
               
               
                   
                 −17 
                 1 
                 1 
                 116 
                 130 
                 25 
               
               
                   
                 −15 
                 1 
                 1 
                 90 
                 97 
                 83 
               
               
                   
                 −13 
                 1 
                 1 
                 377 
                 376 
                 14 
               
               
                   
                 −11 
                 1 
                 1 
                 253 
                 267 
                 10 
               
               
                   
                 −9 
                 1 
                 1 
                 810 
                 820 
                 22 
               
               
                   
                 −7 
                 1 
                 1 
                 413 
                 399 
                 12 
               
               
                   
                 −5 
                 1 
                 1 
                 170 
                 134 
                 11 
               
               
                   
                 −3 
                 1 
                 1 
                 413 
                 410 
                 22 
               
               
                   
                 −1 
                 1 
                 1 
                 1228 
                 1147 
                 108 
               
               
                   
                 1 
                 1 
                 1 
                 757 
                 794 
                 48 
               
               
                   
                 3 
                 1 
                 1 
                 582 
                 574 
                 26 
               
               
                   
                 5 
                 1 
                 1 
                 641 
                 702 
                 19 
               
               
                   
                 7 
                 1 
                 1 
                 110 
                 115 
                 12 
               
               
                   
                 9 
                 1 
                 1 
                 360 
                 340 
                 12 
               
               
                   
                 11 
                 1 
                 1 
                 178 
                 179 
                 12 
               
               
                   
                 13 
                 1 
                 1 
                 113 
                 130 
                 23 
               
               
                   
                 15 
                 1 
                 1 
                 282 
                 245 
                 14 
               
               
                   
                 17 
                 1 
                 1 
                 101 
                 102 
                 29 
               
               
                   
                 −16 
                 2 
                 1 
                 157 
                 110 
                 22 
               
               
                   
                 −14 
                 2 
                 1 
                 156 
                 164 
                 16 
               
               
                   
                 −12 
                 2 
                 1 
                 55 
                 67 
                 54 
               
               
                   
                 12 
                 0 
                 5 
                 559 
                 502 
                 31 
               
               
                   
                 14 
                 0 
                 5 
                 132 
                 90 
                 35 
               
               
                   
                 −19 
                 1 
                 5 
                 168 
                 138 
                 17 
               
               
                   
                 −17 
                 1 
                 5 
                 64 
                 89 
                 64 
               
               
                   
                 −15 
                 1 
                 5 
                 240 
                 237 
                 11 
               
               
                   
                 −13 
                 1 
                 5 
                 307 
                 302 
                 10 
               
               
                   
                 −11 
                 1 
                 5 
                 265 
                 247 
                 9 
               
               
                   
                 −9 
                 1 
                 5 
                 174 
                 149 
                 11 
               
               
                   
                 −7 
                 1 
                 5 
                 993 
                 1009 
                 28 
               
               
                   
                 −5 
                 1 
                 5 
                 835 
                 917 
                 24 
               
               
                   
                 −3 
                 1 
                 5 
                 157 
                 163 
                 10 
               
               
                   
                 −1 
                 1 
                 5 
                 599 
                 623 
                 21 
               
               
                   
                 1 
                 1 
                 5 
                 440 
                 409 
                 12 
               
               
                   
                 3 
                 1 
                 5 
                 422 
                 426 
                 11 
               
               
                   
                 5 
                 1 
                 5 
                 301 
                 324 
                 9 
               
               
                   
                 7 
                 1 
                 5 
                 125 
                 124 
                 13 
               
               
                   
                 9 
                 1 
                 5 
                 95 
                 133 
                 23 
               
               
                   
                 11 
                 1 
                 5 
                 226 
                 221 
                 14 
               
               
                   
                 13 
                 1 
                 5 
                 94 
                 72 
                 34 
               
               
                   
                 −20 
                 2 
                 5 
                 91 
                 83 
                 39 
               
               
                   
                 −18 
                 2 
                 5 
                 163 
                 141 
                 17 
               
               
                   
                 −16 
                 2 
                 5 
                 126 
                 120 
                 19 
               
               
                   
                 −14 
                 2 
                 5 
                 138 
                 138 
                 18 
               
               
                   
                 −12 
                 2 
                 5 
                 133 
                 145 
                 12 
               
               
                   
                 −10 
                 2 
                 5 
                 145 
                 145 
                 11 
               
               
                   
                 −8 
                 2 
                 5 
                 819 
                 840 
                 35 
               
               
                   
                 −6 
                 2 
                 5 
                 282 
                 266 
                 11 
               
               
                   
                 −4 
                 2 
                 5 
                 329 
                 322 
                 15 
               
               
                   
                 −2 
                 2 
                 5 
                 472 
                 481 
                 15 
               
               
                   
                 0 
                 2 
                 5 
                 95 
                 28 
                 14 
               
               
                   
                 2 
                 2 
                 5 
                 142 
                 130 
                 11 
               
               
                   
                 4 
                 2 
                 5 
                 275 
                 289 
                 10 
               
               
                   
                 6 
                 2 
                 5 
                 149 
                 175 
                 13 
               
               
                   
                 8 
                 2 
                 5 
                 102 
                 93 
                 21 
               
               
                   
                 10 
                 2 
                 5 
                 104 
                 111 
                 33 
               
               
                   
                 12 
                 2 
                 5 
                 289 
                 246 
                 16 
               
               
                   
                 −19 
                 3 
                 5 
                 74 
                 16 
                 74 
               
               
                   
                 −17 
                 3 
                 5 
                 64 
                 117 
                 63 
               
               
                   
                 −15 
                 3 
                 5 
                 229 
                 246 
                 21 
               
               
                   
                 −13 
                 3 
                 5 
                 271 
                 279 
                 16 
               
               
                   
                 −11 
                 3 
                 5 
                 169 
                 191 
                 17 
               
               
                   
                 −9 
                 3 
                 5 
                 0 
                 89 
                 1 
               
               
                   
                 −7 
                 3 
                 5 
                 161 
                 189 
                 17 
               
               
                   
                 −5 
                 3 
                 5 
                 0 
                 51 
                 1 
               
               
                   
                 −3 
                 3 
                 5 
                 733 
                 705 
                 31 
               
               
                   
                 −1 
                 3 
                 5 
                 73 
                 96 
                 73 
               
               
                   
                 1 
                 3 
                 5 
                 141 
                 136 
                 11 
               
               
                   
                 3 
                 3 
                 5 
                 74 
                 81 
                 24 
               
               
                   
                 5 
                 3 
                 5 
                 105 
                 93 
                 16 
               
               
                   
                 7 
                 3 
                 5 
                 309 
                 314 
                 11 
               
               
                   
                 9 
                 3 
                 5 
                 28 
                 54 
                 28 
               
               
                   
                 11 
                 3 
                 5 
                 77 
                 72 
                 59 
               
               
                   
                 −16 
                 4 
                 5 
                 110 
                 116 
                 38 
               
               
                   
                 −14 
                 4 
                 5 
                 116 
                 123 
                 36 
               
               
                   
                 −12 
                 4 
                 5 
                 263 
                 215 
                 24 
               
               
                   
                 −10 
                 4 
                 5 
                 138 
                 126 
                 22 
               
               
                   
                 −8 
                 4 
                 5 
                 159 
                 158 
                 18 
               
               
                   
                 −6 
                 4 
                 5 
                 43 
                 80 
                 43 
               
               
                   
                 −4 
                 4 
                 5 
                 86 
                 79 
                 85 
               
               
                   
                 −2 
                 4 
                 5 
                 184 
                 155 
                 20 
               
               
                   
                 0 
                 4 
                 5 
                 138 
                 120 
                 21 
               
               
                   
                 2 
                 4 
                 5 
                 111 
                 118 
                 33 
               
               
                   
                 4 
                 4 
                 5 
                 115 
                 99 
                 41 
               
               
                   
                 6 
                 4 
                 5 
                 99 
                 68 
                 42 
               
               
                   
                 8 
                 4 
                 5 
                 107 
                 123 
                 34 
               
               
                   
                 −13 
                 5 
                 5 
                 0 
                 44 
                 1 
               
               
                   
                 −11 
                 5 
                 5 
                 21 
                 58 
                 21 
               
               
                   
                 −9 
                 5 
                 5 
                 0 
                 35 
                 1 
               
               
                   
                 −7 
                 5 
                 5 
                 149 
                 143 
                 59 
               
               
                   
                 −5 
                 5 
                 5 
                 92 
                 236 
                 91 
               
               
                   
                 −3 
                 5 
                 5 
                 190 
                 193 
                 38 
               
               
                   
                 −1 
                 5 
                 5 
                 294 
                 106 
                 84 
               
               
                   
                 1 
                 5 
                 5 
                 30 
                 83 
                 30 
               
               
                   
                 3 
                 5 
                 5 
                 131 
                 119 
                 88 
               
               
                   
                 5 
                 5 
                 5 
                 0 
                 80 
                 1 
               
               
                   
                 −20 
                 0 
                 6 
                 61 
                 26 
                 61 
               
               
                   
                 −18 
                 0 
                 6 
                 86 
                 62 
                 64 
               
               
                   
                 −16 
                 0 
                 6 
                 62 
                 41 
                 62 
               
               
                   
                 −14 
                 0 
                 6 
                 351 
                 381 
                 19 
               
               
                   
                 −12 
                 0 
                 6 
                 404 
                 410 
                 16 
               
               
                   
                 −10 
                 0 
                 6 
                 212 
                 204 
                 14 
               
               
                   
                 −8 
                 0 
                 6 
                 904 
                 935 
                 39 
               
               
                   
                 −6 
                 0 
                 6 
                 293 
                 281 
                 15 
               
               
                   
                 −4 
                 0 
                 6 
                 339 
                 380 
                 18 
               
               
                   
                 −2 
                 0 
                 6 
                 450 
                 455 
                 21 
               
               
                   
                 0 
                 0 
                 6 
                 478 
                 476 
                 19 
               
               
                   
                 2 
                 0 
                 6 
                 462 
                 413 
                 16 
               
               
                   
                 −9 
                 1 
                 10 
                 232 
                 230 
                 9 
               
               
                   
                 −7 
                 1 
                 10 
                 100 
                 105 
                 14 
               
               
                   
                 −5 
                 1 
                 10 
                 129 
                 130 
                 11 
               
               
                   
                 −3 
                 1 
                 10 
                 557 
                 559 
                 15 
               
               
                   
                 −1 
                 1 
                 10 
                 227 
                 237 
                 10 
               
               
                   
                 1 
                 1 
                 10 
                 121 
                 108 
                 16 
               
               
                   
                 3 
                 1 
                 10 
                 81 
                 83 
                 26 
               
               
                   
                 5 
                 1 
                 10 
                 80 
                 76 
                 36 
               
               
                   
                 7 
                 1 
                 10 
                 163 
                 175 
                 16 
               
               
                   
                 9 
                 1 
                 10 
                 0 
                 27 
                 1 
               
               
                   
                 −20 
                 2 
                 10 
                 106 
                 33 
                 28 
               
               
                   
                 −18 
                 2 
                 10 
                 221 
                 227 
                 15 
               
               
                   
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                 21 
               
               
                   
                 −10 
                 0 
                 17 
                 248 
                 215 
                 21 
               
               
                   
                 −8 
                 0 
                 17 
                 140 
                 101 
                 29 
               
               
                   
                 −6 
                 0 
                 17 
                 61 
                 14 
                 61 
               
               
                   
                 −4 
                 0 
                 17 
                 0 
                 5 
                 1 
               
               
                   
                 −2 
                 0 
                 17 
                 63 
                 18 
                 68 
               
               
                   
                 −21 
                 1 
                 17 
                 0 
                 66 
                 1 
               
               
                   
                 −19 
                 1 
                 17 
                 54 
                 66 
                 54 
               
               
                   
                 −17 
                 1 
                 17 
                 138 
                 81 
                 21 
               
               
                   
                 −15 
                 1 
                 17 
                 85 
                 87 
                 85 
               
               
                   
                 −13 
                 1 
                 17 
                 153 
                 170 
                 17 
               
               
                   
                 −11 
                 1 
                 17 
                 85 
                 68 
                 31 
               
               
                   
                 −9 
                 1 
                 17 
                 172 
                 151 
                 15 
               
               
                   
                 −7 
                 1 
                 17 
                 137 
                 145 
                 17 
               
               
                   
                 −5 
                 1 
                 17 
                 42 
                 59 
                 42 
               
               
                   
                 −3 
                 1 
                 17 
                 0 
                 9 
                 1 
               
               
                   
                 −18 
                 2 
                 17 
                 0 
                 32 
                 1 
               
               
                   
                 −16 
                 2 
                 17 
                 152 
                 104 
                 25 
               
               
                   
                 −14 
                 2 
                 17 
                 182 
                 143 
                 22 
               
               
                   
                 −12 
                 2 
                 17 
                 0 
                 39 
                 1 
               
               
                   
                 −10 
                 2 
                 17 
                 116 
                 99 
                 28 
               
               
                   
                 −8 
                 2 
                 17 
                 178 
                 146 
                 17 
               
               
                   
                 −6 
                 2 
                 17 
                 0 
                 63 
                 1 
               
               
                   
                 −4 
                 2 
                 17 
                 0 
                 46 
                 1 
               
               
                   
                 −13 
                 3 
                 17 
                 47 
                 52 
                 47 
               
               
                   
                 −11 
                 3 
                 17 
                 0 
                 19 
                 1 
               
               
                   
                 −9 
                 3 
                 17 
                 0 
                 62 
                 1 
               
               
                   
                 −20 
                 0 
                 18 
                 0 
                 9 
                 1 
               
               
                   
                 −18 
                 0 
                 18 
                 146 
                 95 
                 29 
               
               
                   
                 −16 
                 0 
                 18 
                 158 
                 123 
                 26 
               
               
                   
                 −14 
                 0 
                 18 
                 128 
                 90 
                 33 
               
               
                   
                 −12 
                 0 
                 18 
                 37 
                 26 
                 37 
               
               
                   
                 −10 
                 0 
                 18 
                 56 
                 30 
                 65 
               
               
                   
                 −8 
                 0 
                 18 
                 0 
                 77 
                 1 
               
               
                   
                 −6 
                 0 
                 18 
                 84 
                 53 
                 58 
               
               
                   
                 −4 
                 0 
                 18 
                 0 
                 36 
                 1 
               
               
                   
                 −19 
                 1 
                 18 
                 106 
                 71 
                 31 
               
               
                   
                 −17 
                 1 
                 18 
                 0 
                 63 
                 1 
               
               
                   
                 −15 
                 1 
                 18 
                 31 
                 19 
                 30 
               
               
                   
                 −13 
                 1 
                 18 
                 0 
                 63 
                 1 
               
               
                   
                 −11 
                 1 
                 18 
                 127 
                 121 
                 19 
               
               
                   
                 −9 
                 1 
                 18 
                 0 
                 71 
                 1 
               
               
                   
                 −7 
                 1 
                 18 
                 69 
                 41 
                 46 
               
               
                   
                 −5 
                 1 
                 18 
                 112 
                 70 
                 48 
               
               
                   
                 −16 
                 2 
                 18 
                 84 
                 53 
                 58 
               
               
                   
                 −14 
                 2 
                 18 
                 191 
                 129 
                 26 
               
               
                   
                 −12 
                 2 
                 18 
                 122 
                 92 
                 31 
               
               
                   
                 −10 
                 2 
                 18 
                 66 
                 32 
                 65 
               
               
                   
                 −8 
                 2 
                 18 
                 0 
                 55 
                 1 
               
               
                   
                 −18 
                 0 
                 19 
                 86 
                 25 
                 62 
               
               
                   
                 −16 
                 0 
                 19 
                 0 
                 75 
                 1 
               
               
                   
                 −14 
                 0 
                 19 
                 71 
                 66 
                 71 
               
               
                   
                 −12 
                 0 
                 19 
                 105 
                 58 
                 39 
               
               
                   
                 −10 
                 0 
                 19 
                 0 
                 37 
                 1 
               
               
                   
                 −8 
                 0 
                 19 
                 42 
                 52 
                 42 
               
               
                   
                 −17 
                 1 
                 19 
                 76 
                 81 
                 64 
               
               
                   
                 −15 
                 1 
                 19 
                 132 
                 134 
                 20 
               
               
                   
                 −13 
                 1 
                 19 
                 0 
                 56 
                 1 
               
               
                   
                 −11 
                 1 
                 19 
                 90 
                 70 
                 30 
               
               
                   
                 −15 
                 1 
                 20 
                 153 
                 100 
                 74 
               
               
                   
                   
               
             
          
         
       
     
     References 
     1. CrysAlis RED, Oxford Diffraction Ltd., Version 1.171.28cycle2 beta (release 25-10-2005 CrysAlis171.NET) (compiled Oct. 25,2005, 08:50:05). Empirical absorption correction using spherical harmonics, implemented in SCALES ABSPACK scaling algorithm. 
     2. CrysAlis CCD, Oxford Diffraction Ltd., Version L171.28cycle2 beta; CrysAlis RED, Oxford Diffraction Ltd., Version l.171.29cycle2 beta. 
     3. G. M. Sheldrick, Acta Crystallogr. 1990, A46, 467-473. 
     4. G. M. Sheldrick, SHELXL93,  Program for the Reminement of Crystal Structures. , Univ., of Göttingen, Germany. 
     5.  International Tables far Crystallography , Ed. A. J. C. Wilson, Kluwer:Dordrecth, 1992, Vol.C. 
     Example 2 
     Synthesis of F-24. The preparation of F-24 having the basic structure I can be accomplished by a common general method otherwise referred to as the condensation of a bicyclic Windaus-Grundmann type ketone II with the allylic phosphine oxide III to the corresponding 19-nor-vitamin D analog IV followed by deprotection at C-1 and C-3 in the latter compound IV to obtain compound 1 (F-24). 
     
       
                 
         
             
             
         
      
     
     In phosphine oxide III, Y 1  and Y 2  are preferably hydroxy-protecting groups such as silyl protecting groups. The t-butyldimethylsilyl (TMDMS) group is an example of a particularly useful hydroxy-protecting group. The process described above represents an application of the convergent synthesis concept, which has been applied effectively to the preparation of numerous vitamin D compounds (see Lythgoe et al.,  J. Chem. Soc. Perkin Trans.  1, 590 (1978); Lythgoe,  Chem. Soc. Rev.  9, 449 (1983): Toh et al.,  J. Org. Chem.  48, 1414 (1983); Baggiolini et al.,  J. Org. Chem.  51, 3098 (1986); Sardina et al,  J. Org. Chem.  51, 1264 (1986);  J. Org. Chem.  51, 1269 (1986); DeLuca et al., U.S. Pat. No. 5,086,191; DeLuca et al., U.S. Pat. No. 5,536,713; and DeLuca et al., U.S. Pat. No. 5,843,928 all of which are hereby incorporated by reference in their entirety and for all purposes as if fully set forth herein. 
     Phosphine oxide III is a convenient reagent that can be used to prepare a large number of 19-nor-vitamin D compounds and is prepared according to the procedures described by Sicinski et al.,  J. Med. Chem.,  41, 4662 (1998), DeLuca et al., U.S. Pat. No. 5,843,928; Perlman et al.,  Tetrahedron Lett.  32, 7663 (1991); and DeLuca et al., U.S. Pat. No. 5,086,195 which are hereby incorporated by reference in their entirety as if fully set forth herein. 
     An overall process for the synthesis of compound I is illustrated and described more completely in U.S. Pat. No. 5,843,928 entitled “2-Alkylidene-19-Nor-Vitamin D Compounds,” the specification of which is specifically incorporated herein by reference.