PATENT ABSTRACT
Disclosed are methods of purifying the compound (20R)-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.

PATENT DESCRIPTION
CROSS-REFERENCE TO RELATED PATENT APPLICATIONS 
       [0001]    The present application claims the benefit under 35 U.S.C. §119(e) to U.S. Provisional Patent Application No. 61/652,949, filed on May 30, 2012, the content of which is incorporated herein by reference in its entirety. 
     
    
     STATEMENT REGARDING FEDERALLY SPONSORED RESEARCH OR DEVELOPMENT 
       [0002]    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 
       [0003]    The field of the present invention relates to purification of organic compounds, and more particularly to the purification of the compound (20R)-19-nor-24-difluoro-1α, 25-dihydroxyvitamin D 3  (referred to herein as “24F2-DM”) by preparing the compound in crystalline form. 
         [0004]    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. 
         [0005]    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 Nevinckx et al.,  Tetrahedron  47, 9419 (1991); Vanmaele et al.,  Tetrahedron  41, 141 (1985) and 40, 1179 (1994); Vanmaele et 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. Sci. 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-hydroxyvitamin 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. 
         [0006]    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. 
         [0007]    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 24F2-DM is required. 
       SUMMARY 
       [0008]    Disclosed herein are methods of purifying 24F2-DM by means of crystallization to obtain 24F2-DM 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 24F2-DM, the most appropriate solvent and/or solvent system is characterized by the following factors: 
         [0009]    (1) low toxicity; 
         [0010]    (2) low boiling point; 
         [0011]    (3) significant dependence of solubility properties with regard to temperature (condition necessary for providing satisfactory crystallization yield); and 
         [0012]    (4) relatively low cost. 
         [0013]    Interestingly, hexane, so frequently used for crystallization purposes, was found less suitable as the sole solvent for crystallization of 24F2-DM. However, it was found that a mixture of 2-propanol and hexane was most useful for the crystallization of 24F2-DM. 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. 
         [0014]    Accordingly, the present invention provides a compound having the formula: 
         [0000]    
       
                 
         
             
             
         
       
     
         [0000]    in crystalline form. More specifically, the compound may be referred to as (20R)-19-nor-24-difluoro-1α,25-dihydroxyvitamin D 3  or “24F2-DM” in crystalline form. 
     
    
     
       BRIEF DESCRIPTION OF THE DRAWINGS 
         [0015]      FIG. 1  is an illustration of the three dimensional molecular structure for 24F2-DM as defined by the atomic positional parameters discovered and set forth herein. 
       
    
    
     DETAILED DESCRIPTION 
       [0016]    Disclosed herein is the compound (20R)-19-nor-24-difluoro-1α,25-dihydroxyvitamin D3 (24F2-DM) in crystalline form, a pharmacologically important compound, characterized by the formula I shown below: 
         [0000]    
       
                 
         
             
             
         
       
     
         [0017]    Also disclosed are methods of purifying 24F2-DM. The purification technique involves obtaining the 24F2-DM 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 24F2-DM. 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 24F2-DM 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 24F2-DM to be purified. 
       EXAMPLES 
       [0018]    The following examples are illustrative and should not be interpreted as limiting the claimed subject matter. 
         [0019]    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 182-183° C. (24F2-DM). 
         [0020]    The described crystallization process of the synthetic 24F2-DM 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)-19-nor-24-difluoro-1α25-dihydroxyvitamin D 3  (24F2-DM) 
       [0021]    Crystallization from 2-Propanol/Hexane. 
         [0022]    (20R)-19-nor-24-difluoro-1α,25-dihydroxyvitamin D 3  (24F2-DM) (6 mg), was suspended in hexane (3 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). 
         [0023]    Experimental. 
         [0024]    A colorless prism-shaped crystal of dimensions 0.56×0.24×0.21 mm was selected for structural analysis. Intensity data were collected using a Bruker AXS Platinum 135 CCD detector controlled with the PROTEUM software suite (Bruker AXS Inc., Madison, Wis.). The x-ray source was CuKα radiation (1.54178 Å) 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 7.06 A (Bruker AXS Inc.) and internally scaled with SADABS version 2005/1 (Bruker AXS Inc.). The sample was mounted in a quartz capillary and diffraction data collected at 298 K. The intensity data were measured as a series of phi and omega oscillation frames each of 1° for 30-60 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 5115 peaks in the range of 3.0&lt;theta&lt;61.5°. The data were merged to form a set of 2949 independent data with R(int)=0.0658. 
         [0025]    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, Bruker AXS Inc.; (b)  International Tables for Crysuallography, 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 280 parameters were refined against 1 restraint and 2949 data to give wR2=0.1794 and S=1.027 for weights of w=1/[s 2 (F 2 )+(0.1196P) 2 ], where P=[F o   2 +2F 2 ]/3. The final R(F) was 0.0669 for the 2949 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 0.228 and −0.200 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). 
         [0026]    The three dimensional structure of 24F2-DM as defined by the following physical data and atomic positional parameters described and calculated herein (Tables 1-8) is illustrated in  FIG. 1 . 
         [0000]    
       
         
               
             
               
               
             
               
               
               
             
               
               
             
           
               
                 TABLE 1 
               
               
                   
               
               
                 Crystal data and structure refinement for 24F2-DM. 
               
               
                   
               
             
             
               
                   
               
             
          
           
               
                 Identification code 
                 2007 feb. 11 
               
               
                 Empirical formula 
                 C26H42F2O3 
               
               
                 Formula weight 
                  440.60 
               
               
                 Temperature 
                 298(2) K 
               
               
                 Wavelength 
                 1.54178 Å 
               
               
                 Crystal system 
                 Monoclinic 
               
               
                 Space group 
                 C2 
               
             
          
           
               
                 Unit cell dimensions 
                 a = 23.882(5) Å 
                 α = 90° 
               
               
                   
                 b = 6.1654(12) Å 
                 β = 121.83(3)° 
               
               
                   
                 c = 19.632(4) Å 
                 γ = 90° 
               
             
          
           
               
                 Volume 
                 2456.0(8) Å 3   
               
               
                 Z 
                   4 
               
               
                 Density (calculated) 
                 1.192 Mg/m 3   
               
               
                 Absorption coefficient 
                 0.696 mm −1   
               
               
                 F(000) 
                  960 
               
               
                 Crystal size 
                 0.70 × 0.20 × 0.01 mm 
               
               
                 Theta range for data collection 
                 2.65 to 62.79° 
               
               
                 Limiting indices 
                 −27 &lt; h &lt; 26, −7 &lt; k &lt; 5, −22 &lt; l &lt; 20 
               
               
                 Reflections collected 
                 5115 
               
               
                 Independent reflections 
                 2949 (R(int) = 0.0658) 
               
               
                 Completeness to Theta = 62.79 
                 97.4% 
               
               
                 Max. and min. transmission 
                 0.9931 and 0.6415 
               
               
                 Refinement method 
                 Full-matrix least-squares on F 2   
               
               
                 Data/restraints/parameters 
                 2949/1/280 
               
               
                 Goodness-of-fit on F 2   
                   1.027 
               
               
                 Final R indices [I &gt; 2σ(I)] 
                 R1 = 0.0669, wR2 = 0.1794 
               
               
                 R indices (all data) 
                 R1 = 0.0812, wR2 = 0.1938 
               
               
                 Largest diff. peak and hole 
                 0.228 and −0.200 e − /Å 3   
               
               
                   
               
             
          
         
       
     
         [0000]    
       
         
               
             
               
               
               
               
               
             
               
               
               
               
               
               
             
           
               
                 TABLE 2 
               
             
             
               
                   
               
               
                 Atomic coordinates (Å 2  × 10 4 ) and equivalent isotropic 
               
               
                 displacement parameters (Å 2  × 10 3 ) for 24F2-DM U(eq) 
               
               
                 is defined as one third of the trace of the orthogonalized Uij tensor. 
               
             
          
           
               
                   
                 x 
                 y 
                 z 
                 U(eq) 
               
               
                   
                   
               
             
          
           
               
                   
                 O(1) 
                 7791(2) 
                  7357(6) 
                 9362(2) 
                 65(1) 
               
               
                   
                 O(2) 
                 8325(2) 
                 13611(6) 
                 10408(2)  
                 67(1) 
               
               
                   
                 C(13) 
                 9071(2) 
                 14375(7) 
                 6662(2) 
                 46(1) 
               
               
                   
                 F(2) 
                 7592(1) 
                 11566(8) 
                 2797(2) 
                 85(1) 
               
               
                   
                 C(5) 
                 8998(2) 
                 11683(8) 
                 9616(2) 
                 51(1) 
               
               
                   
                 F(1) 
                 8124(2) 
                  8914(7) 
                 3583(2) 
                 97(1) 
               
               
                   
                 C(14) 
                 8581(2) 
                 14018(8) 
                 6948(2) 
                 50(1) 
               
               
                   
                 C(3) 
                 8802(2) 
                 11904(8) 
                 10755(2)  
                 56(1) 
               
               
                   
                 C(2) 
                 8472(2) 
                  9722(8) 
                 10504(3)  
                 58(1) 
               
               
                   
                 O(25) 
                 8404(2) 
                 11739(8) 
                 2212(2) 
                 75(1) 
               
               
                   
                 C(4) 
                 9288(2) 
                  12202(10) 
                 10482(2)  
                 59(1) 
               
               
                   
                 C(8) 
                 8875(2) 
                 14304(8) 
                 7829(2) 
                 50(1) 
               
               
                   
                 C(10) 
                 8646(3) 
                  9530(8) 
                 9360(3) 
                 60(1) 
               
               
                   
                 C(11) 
                 9669(3) 
                 17024(9) 
                 7815(2) 
                 64(1) 
               
               
                   
                 C(1) 
                 8146(2) 
                  9375(8) 
                 9611(3) 
                 54(1) 
               
               
                   
                 C(7) 
                 8823(2) 
                 12846(8) 
                 8292(2) 
                 52(1) 
               
               
                   
                 C(6) 
                 9065(2) 
                 13067(8) 
                 9137(3) 
                 54(1) 
               
               
                   
                 C(12) 
                 9342(2) 
                 16680(8) 
                 6912(2) 
                 57(1) 
               
               
                   
                 C(18) 
                 9627(2) 
                 12723(8) 
                 7044(2) 
                 54(1) 
               
               
                   
                 C(15) 
                 8230(2) 
                  11923(10) 
                 6537(3) 
                 61(1) 
               
               
                   
                 C(17) 
                 8612(2) 
                 13954(8) 
                 5760(2) 
                 52(1) 
               
               
                   
                 C(9) 
                 9199(3) 
                 16504(9) 
                 8103(3) 
                 64(1) 
               
               
                   
                 C(20) 
                 8910(2) 
                 13579(9) 
                 5242(2) 
                 57(1) 
               
               
                   
                 C(27) 
                 9084(3) 
                  9004(14) 
                 3081(3) 
                 88(2) 
               
               
                   
                 C(16) 
                 8177(2) 
                  12029(10) 
                 5721(2) 
                 64(1) 
               
               
                   
                 C(23) 
                 8654(2) 
                  12262(10) 
                 3874(3) 
                 68(2) 
               
               
                   
                 C(24) 
                 8202(2) 
                  10696(10) 
                 3226(3) 
                 63(1) 
               
               
                   
                 C(25) 
                 8401(2) 
                  9895(10) 
                 2645(3) 
                 63(1) 
               
               
                   
                 C(22) 
                 8382(2) 
                  12996(12) 
                 4384(2) 
                 71(2) 
               
               
                   
                 C(26) 
                 7907(3) 
                  8192(12) 
                 2071(3) 
                 82(2) 
               
               
                   
                 C(21) 
                 9300(4) 
                  15514(14) 
                 5254(3) 
                 99(2) 
               
               
                   
                   
               
             
          
         
       
     
         [0000]    
       
         
               
             
               
               
               
             
           
               
                 TABLE 3 
               
               
                   
               
               
                 Bond lengths [Å] for 24F2-DM. 
               
               
                   
               
             
             
               
                   
               
             
          
           
               
                   
                 O(1)—C(1) 
                 1.439(6) 
               
               
                   
                 O(1)—H(1A) 
                 0.8200 
               
               
                   
                 O(2)—C(3) 
                 1.432(6) 
               
               
                   
                 O(2)—H(2A) 
                 0.8200 
               
               
                   
                 C(13)—C(18) 
                 1.521(6) 
               
               
                   
                 C(13)—C(17) 
                 1.537(6) 
               
               
                   
                 C(13)—C(12) 
                 1.531(6) 
               
               
                   
                 C(13)—C(14) 
                 1.558(6) 
               
               
                   
                 F(2)—C(24) 
                 1.353(6) 
               
               
                   
                 C(5)—C(6) 
                 1.341(7) 
               
               
                   
                 C(5)—C(4) 
                 1.493(6) 
               
               
                   
                 C(5)—C(10) 
                 1.508(7) 
               
               
                   
                 F(1)—C(24) 
                 1.368(7) 
               
               
                   
                 C(14)—C(8) 
                 1.494(6) 
               
               
                   
                 C(14)—C(15) 
                 1.519(7) 
               
               
                   
                 C(14)—H(14A) 
                 0.9800 
               
               
                   
                 C(3)—C(2) 
                 1.505(7) 
               
               
                   
                 C(3)—C(4) 
                 1.524(6) 
               
               
                   
                 C(3)—H(3A) 
                 0.9800 
               
               
                   
                 C(2)—C(1) 
                 1.511(6) 
               
               
                   
                 C(2)—H(2B) 
                 0.9700 
               
               
                   
                 O(2)—H(2C) 
                 0.9700 
               
               
                   
                 O(25)—C(25) 
                 1.422(7) 
               
               
                   
                 O(25)—H(25A) 
                 0.8200 
               
               
                   
                 C(4)—H(4A) 
                 0.9700 
               
               
                   
                 C(4)—H(4B) 
                 0.9700 
               
               
                   
                 C(8)—C(7) 
                 1.330(6) 
               
               
                   
                 C(8)—C(9) 
                 1.513(7) 
               
               
                   
                 C(10)—C(1) 
                 1.517(6) 
               
               
                   
                 C(10)—H(10A) 
                 0.9700 
               
               
                   
                 C(10)—H(10B) 
                 0.9700 
               
               
                   
                 C(11)—C(9) 
                 1.532(7) 
               
               
                   
                 C(11)—C(12) 
                 1.529(6) 
               
               
                   
                 C(11)—H(11A) 
                 0.9700 
               
               
                   
                 C(11)—H(11B) 
                 0.9700 
               
               
                   
                 C(1)—H(1B) 
                 0.9800 
               
               
                   
                 C(7)—C(6) 
                 1.446(6) 
               
               
                   
                 C(7)—H(7A) 
                 0.9300 
               
               
                   
                 C(6)—H(6A) 
                 0.9300 
               
               
                   
                 C(12)—H(12A) 
                 0.9700 
               
               
                   
                 C(12)—H(12B) 
                 0.9700 
               
               
                   
                 C(18)—H(18A) 
                 0.9600 
               
               
                   
                 C(18)—H(18B) 
                 0.9600 
               
               
                   
                 C(18)—H(18C) 
                 0.9600 
               
               
                   
                 C(15)—C(16) 
                 1.541(6) 
               
               
                   
                 C(15)—H(15A) 
                 0.9700 
               
               
                   
                 C(15)—H(15B) 
                 0.9700 
               
               
                   
                 C(17)—C(20) 
                 1.536(6) 
               
               
                   
                 C(17)—C(16) 
                 1.552(7) 
               
               
                   
                 C(17)—H(17A) 
                 0.9800 
               
               
                   
                 C(9)—H(9A) 
                 0.9700 
               
               
                   
                 C(9)—H(9B) 
                 0.9700 
               
               
                   
                 C(20)—C(21) 
                 1.506(8) 
               
               
                   
                 C(20)—C(22) 
                 1.522(6) 
               
               
                   
                 C(20)—H(20A) 
                 0.9800 
               
               
                   
                 C(27)—C(25) 
                 1.489(8) 
               
               
                   
                 C(27)—H(27A) 
                 0.9600 
               
               
                   
                 C(27)—H(27B) 
                 0.9600 
               
               
                   
                 C(27)—H(27C) 
                 0.9600 
               
               
                   
                 C(16)—H(16A) 
                 0.9700 
               
               
                   
                 C(16)—H(16B) 
                 0.9700 
               
               
                   
                 C(23)—C(24) 
                 1.505(7) 
               
               
                   
                 C(23)—C(22) 
                 1.520(6) 
               
               
                   
                 C(23)—H(23A) 
                 0.9700 
               
               
                   
                 C(23)—H(23B) 
                 0.9700 
               
               
                   
                 C(24)—C(25) 
                 1.530(7) 
               
               
                   
                 C(25)—C(26) 
                 1.537(8) 
               
               
                   
                 C(22)—H(22A) 
                 0.9700 
               
               
                   
                 C(22)—H(22B) 
                 0.9700 
               
               
                   
                 C(26)—H(26A) 
                 0.9600 
               
               
                   
                 C(26)—H(26B) 
                 0.9600 
               
               
                   
                 C(26)—H(26C) 
                 0.9600 
               
               
                   
                 C(21)—H(21A) 
                 0.9600 
               
               
                   
                 C(21)—H(21B) 
                 0.9600 
               
               
                   
                 C(21)—H(21C) 
                 0.9600 
               
               
                   
                   
               
             
          
         
       
     
         [0000]    
       
         
               
             
               
               
               
             
           
               
                 TABLE 4 
               
               
                   
               
               
                 Bond angles [°] for 24F2-DM. 
               
               
                   
               
             
             
               
                   
               
             
          
           
               
                   
                 C(1)—O(1)—H(1A) 
                 109.5 
               
               
                   
                 C(3)—O(2)—H(2A) 
                 109.5 
               
               
                   
                 C(18)—C(13)—C(17) 
                 111.2(4) 
               
               
                   
                 C(18)—C(13)—C(12) 
                 110.6(4) 
               
               
                   
                 C(17)—C(13)—C(12) 
                 116.8(4) 
               
               
                   
                 C(18)—C(13)—C(14) 
                 110.8(3) 
               
               
                   
                 C(17)—C(13)—C(14) 
                 100.1(3) 
               
               
                   
                 C(12)—C(13)—C(14) 
                 106.6(3) 
               
               
                   
                 C(6)—C(5)—C(4) 
                 120.5(5) 
               
               
                   
                 C(6)—C(5)—C(10) 
                 125.2(4) 
               
               
                   
                 C(4)—C(5)—C(10) 
                 114.3(4) 
               
               
                   
                 C(8)—C(14)—C(15) 
                 120.4(4) 
               
               
                   
                 C(8)—C(14)—C(13) 
                 114.5(3) 
               
               
                   
                 C(15)—C(14)—C(13) 
                 103.7(3) 
               
               
                   
                 C(8)—C(14)—H(14A) 
                 105.7 
               
               
                   
                 C(15)—C(14)—H(14A) 
                 105.7 
               
               
                   
                 C(13)—C(14)—H(14A) 
                 105.7 
               
               
                   
                 O(2)—C(3)—C(2) 
                 110.7(3) 
               
               
                   
                 O(2)—C(3)—C(4) 
                 107.7(4) 
               
               
                   
                 C(2)—C(3)—C(4) 
                 110.9(4) 
               
               
                   
                 O(2)—C(3)—H(3A) 
                 109.2 
               
               
                   
                 C(2)—C(3)—H(3A) 
                 109.2 
               
               
                   
                 C(4)—C(3)—H(3A) 
                 109.2 
               
               
                   
                 C(1)—C(2)—C(3) 
                 111.5(4) 
               
               
                   
                 C(1)—C(2)—H(2B) 
                 109.3 
               
               
                   
                 C(3)—C(2)—H(2B) 
                 109.3 
               
               
                   
                 C(1)—C(2)—H(2C) 
                 109.3 
               
               
                   
                 C(3)—C(2)—H(2C) 
                 109.3 
               
               
                   
                 H(2B)—C(2)—H(2C) 
                 108.0 
               
               
                   
                 C(25)—O(25)—H(25A) 
                 109.5 
               
               
                   
                 C(5)—C(4)—C(3) 
                 113.2(4) 
               
               
                   
                 C(5)—C(4)—H(4A) 
                 108.9 
               
               
                   
                 C(3)—C(4)—H(4A) 
                 108.9 
               
               
                   
                 C(5)—C(4)—H(4B) 
                 108.9 
               
               
                   
                 C(3)—C(4)—H(4B) 
                 108.9 
               
               
                   
                 H(4A)—C(4)—H(4B) 
                 107.8 
               
               
                   
                 C(7)—C(8)—C(14) 
                 123.7(4) 
               
               
                   
                 C(7)—C(8)—C(9) 
                 125.2(4) 
               
               
                   
                 C(14)—C(8)—C(9) 
                 111.0(4) 
               
               
                   
                 C(5)—C(10)—C(1) 
                 110.0(4) 
               
               
                   
                 C(5)—C(10)—H(10A) 
                 109.7 
               
               
                   
                 C(1)—C(10)—H(10A) 
                 109.7 
               
               
                   
                 C(5)—C(10)—H(10B) 
                 109.7 
               
               
                   
                 C(1)—C(10)—H(10B) 
                 109.7 
               
               
                   
                 H(10A)—C(10)—H(10B) 
                 108.2 
               
               
                   
                 C(9)—C(11)—C(12) 
                 111.8(4) 
               
               
                   
                 C(9)—C(11)—H(11A) 
                 109.3 
               
               
                   
                 C(12)—C(11)—H(11A) 
                 109.3 
               
               
                   
                 C(9)—C(11)—H(11B) 
                 109.2 
               
               
                   
                 C(12)—C(11)—H(11B) 
                 109.3 
               
               
                   
                 H(11A)—C(11)—H(11B) 
                 107.9 
               
               
                   
                 O(1)—C(1)—C(2) 
                 111.6(4) 
               
               
                   
                 O(1)—C(1)—C(10) 
                 111.5(4) 
               
               
                   
                 C(2)—C(1)—C(10) 
                 110.9(4) 
               
               
                   
                 O(1)—C(1)—H(1B) 
                 107.5 
               
               
                   
                 C(2)—C(1)—H(1B) 
                 107.5 
               
               
                   
                 C(10)—C(1)—H(1B) 
                 107.5 
               
               
                   
                 C(8)—C(7)—C(6) 
                 126.6(5) 
               
               
                   
                 C(8)—C(7)—H(7A) 
                 116.7 
               
               
                   
                 C(6)—C(7)—H(7A) 
                 116.7 
               
               
                   
                 C(5)—C(6)—C(7) 
                 128.4(5) 
               
               
                   
                 C(5)—C(6)—H(6A) 
                 115.8 
               
               
                   
                 C(7)—C(6)—H(6A) 
                 115.8 
               
               
                   
                 C(11)—C(12)—C(13) 
                 111.8(4) 
               
               
                   
                 C(11)—C(12)—H(12A) 
                 109.2 
               
               
                   
                 C(13)—C(12)—H(12A) 
                 109.2 
               
               
                   
                 C(11)—C(12)—H(12B) 
                 109.2 
               
               
                   
                 C(13)—C(12)—H(12B) 
                 109.2 
               
               
                   
                 H(12A)—C(12)—H(12B) 
                 107.9 
               
               
                   
                 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(14)—C(15)—C(16) 
                 103.7(4) 
               
               
                   
                 C(14)—C(15)—H(15A) 
                 111.0 
               
               
                   
                 C(16)—C(15)—H(15A) 
                 111.0 
               
               
                   
                 C(14)—C(15)—H(15B) 
                 111.0 
               
               
                   
                 C(16)—C(15)—H(15B) 
                 111.0 
               
               
                   
                 H(15A)—C(15)—H(15B) 
                 109.0 
               
               
                   
                 C(13)—C(17)—C(20) 
                 119.4(4) 
               
               
                   
                 C(13)—C(17)—C(16) 
                 103.8(3) 
               
               
                   
                 C(20)—C(17)—C(16) 
                 112.6(4) 
               
               
                   
                 C(13)—C(17)—H(17A) 
                 106.8 
               
               
                   
                 C(20)—C(17)—H(17A) 
                 106.8 
               
               
                   
                 C(16)—C(17)—H(17A) 
                 106.8 
               
               
                   
                 C(8)—C(9)—C(11) 
                 113.2(4) 
               
               
                   
                 C(8)—C(9)—H(9A) 
                 108.9 
               
               
                   
                 C(11)—C(9)—H(9B) 
                 108.9 
               
               
                   
                 C(8)—C(9)—H(9B) 
                 108.9 
               
               
                   
                 C(11)—C(9)—H(9B) 
                 108.9 
               
               
                   
                 H(9A)—C(9)—H(9B) 
                 107.8 
               
               
                   
                 C(21)—C(20)—C(22) 
                 110.4(4) 
               
               
                   
                 C(21)—C(20)—C(17) 
                 111.7(4) 
               
               
                   
                 C(22)—C(20)—C(17) 
                 111.5(4) 
               
               
                   
                 C(21)—C(20)—H(20A) 
                 107.7 
               
               
                   
                 C(22)—C(20)—H(20A) 
                 107.7 
               
               
                   
                 C(17)—C(20)—H(20A) 
                 107.7 
               
               
                   
                 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(15)—C(16)—C(17) 
                 107.2(4) 
               
               
                   
                 C(15)—C(16)—H(16A) 
                 110.3 
               
               
                   
                 C(17)—C(16)—H(16A) 
                 110.3 
               
               
                   
                 C(15)—C(16)—H(16B) 
                 110.3 
               
               
                   
                 C(17)—C(16)—H(16B) 
                 110.3 
               
               
                   
                 H(16A)—C(16)—H(16B) 
                 108.5 
               
               
                   
                 C(24)—C(23)—C(22) 
                 112.5(4) 
               
               
                   
                 C(24)—C(23)—H(23A) 
                 109.1 
               
               
                   
                 C(22)—C(23)—H(23A) 
                 109.1 
               
               
                   
                 C(24)—C(23)—H(23B) 
                 109.1 
               
               
                   
                 C(22)—C(23)—H(23B) 
                 109.1 
               
               
                   
                 H(23A)—C(23)—H(23B) 
                 107.8 
               
               
                   
                 F(2)—C(24)—F(1) 
                 104.1(4) 
               
               
                   
                 F(2)—C(24)—C(23) 
                 109.2(5) 
               
               
                   
                 F(1)—C(24)—C(23) 
                 108.2(4) 
               
               
                   
                 F(2)—C(24)—C(25) 
                 108.7(3) 
               
               
                   
                 F(1)—C(24)—C(25) 
                 107.6(5) 
               
               
                   
                 C(23)—C(24)—C(25) 
                 118.1(4) 
               
               
                   
                 O(25)—C(25)—C(27) 
                 106.9(5) 
               
               
                   
                 O(25)—C(25)—C(24) 
                 106.8(5) 
               
               
                   
                 C(27)—C(25)—C(24) 
                 111.5(4) 
               
               
                   
                 O(25)—C(25)—C(26) 
                 110.6(4) 
               
               
                   
                 C(27)—C(25)—C(26) 
                 110.8(5) 
               
               
                   
                 C(24)—C(25)—C(26) 
                 110.2(4) 
               
               
                   
                 C(23)—C(22)—C(20) 
                 114.0(4) 
               
               
                   
                 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(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(26C) 
                 109.5 
               
               
                   
                 H(26A)—C(26)—H(26C) 
                 109.5 
               
               
                   
                 H(26B)—C(26)—H(26C) 
                 109.5 
               
               
                   
                 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(21C) 
                 109.5 
               
               
                   
                 H(21A)—C(21)—H(21C) 
                 109.5 
               
               
                   
                 H(21B)—C(21)—H(21C) 
                 109.5 
               
               
                   
                   
               
             
          
         
       
     
         [0000]    
       
         
               
             
               
               
               
               
               
               
               
             
           
               
                 TABLE 5 
               
             
             
               
                   
               
               
                 Anisotropic displacement parameters (Å 2  × 
               
               
                 10 3 ) for 24F2-DM. The anisotropic displacement factor exponent takes the 
               
               
                 form: −2π 2 [h 2 a* 2 U 11  + . . . + 2hka*b*U 12 . 
               
             
          
           
               
                   
                 U11 
                 U22 
                 U33 
                 U23 
                 U13 
                 U12 
               
               
                   
               
               
                 O(1) 
                 75 (2) 
                 56 (2) 
                 64 (2) 
                 0 (2) 
                 37 (2) 
                 −12 (2)  
               
               
                 O(2) 
                 85 (2) 
                 55 (2) 
                 82 (2) 
                 4 (2) 
                 57 (2) 
                  1 (2) 
               
               
                 C(13) 
                 53 (2) 
                 40 (2) 
                 49 (2) 
                 2 (2) 
                 30 (2) 
                  3 (2) 
               
               
                 F(2) 
                 60 (2) 
                 125 (3)  
                 63 (1) 
                 −17 (2)  
                 28 (1) 
                  1 (2) 
               
               
                 C(5) 
                 55 (2) 
                 52 (3) 
                 58 (2) 
                 −1 (2)  
                 37 (2) 
                 −4 (2) 
               
               
                 F(1) 
                 127 (3)  
                 100 (3)  
                 91 (2) 
                 3 (2) 
                 75 (2) 
                 −28 (2)  
               
               
                 C(14) 
                 54 (2) 
                 44 (2) 
                 58 (2) 
                 2 (2) 
                 34 (2) 
                  0 (2) 
               
               
                 C(3) 
                 62 (2) 
                 56 (3) 
                 54 (2) 
                 4 (2) 
                 34 (2) 
                 −1 (2) 
               
               
                 C(2) 
                 63 (2) 
                 54 (3) 
                 58 (2) 
                 11 (2)  
                 38 (2) 
                 −1 (2) 
               
               
                 O(25) 
                 90 (2) 
                 83 (3) 
                 60 (2) 
                 6 (2) 
                 45 (2) 
                 −5 (2) 
               
               
                 C(4) 
                 56 (2) 
                 72 (3) 
                 49 (2) 
                 2 (2) 
                 28 (2) 
                 −4 (2) 
               
               
                 C(8) 
                 57 (2) 
                 47 (3) 
                 59 (2) 
                 1 (2) 
                 38 (2) 
                  3 (2) 
               
               
                 C(10) 
                 80 (3) 
                 54 (3) 
                 62 (2) 
                 −1 (2)  
                 48 (2) 
                 −1 (3) 
               
               
                 C(11) 
                 90 (3) 
                 49 (3) 
                 56 (2) 
                 −4 (2)  
                 40 (2) 
                 −17 (3)  
               
               
                 C(1) 
                 63 (2) 
                 45 (3) 
                 61 (2) 
                 8 (2) 
                 37 (2) 
                  0 (2) 
               
               
                 C(7) 
                 62 (2) 
                 50 (3) 
                 58 (2) 
                 −2 (2)  
                 42 (2) 
                 −3 (2) 
               
               
                 C(6) 
                 56 (2) 
                 52 (3) 
                 62 (2) 
                 −1 (2)  
                 36 (2) 
                  0 (2) 
               
               
                 C(12) 
                 71 (3) 
                 42 (3) 
                 63 (2) 
                 0 (2) 
                 40 (2) 
                 −9 (3) 
               
               
                 C(18) 
                 55 (2) 
                 53 (3) 
                 52 (2) 
                 −1 (2)  
                 26 (2) 
                  3 (2) 
               
               
                 C(15) 
                 63 (2) 
                 66 (3) 
                 67 (2) 
                 −6 (3)  
                 42 (2) 
                 −12 (3)  
               
               
                 C(17) 
                 57 (2) 
                 52 (3) 
                 50 (2) 
                 1 (2) 
                 31 (2) 
                  5 (2) 
               
               
                 C(9) 
                 94 (3) 
                 46 (3) 
                 59 (2) 
                 −9 (2)  
                 44 (2) 
                 −6 (3) 
               
               
                 C(20) 
                 58 (2) 
                 67 (3) 
                 52 (2) 
                 −5 (2)  
                 32 (2) 
                 −5 (2) 
               
               
                 C(27) 
                 81 (3) 
                 109 (6)  
                 76 (3) 
                 6 (4) 
                 43 (3) 
                  8 (4) 
               
               
                 C(16) 
                 69 (3) 
                 66 (3) 
                 59 (2) 
                 −3 (3)  
                 35 (2) 
                 −6 (3) 
               
               
                 C(23) 
                 70 (3) 
                 89 (4) 
                 53 (2) 
                 −11 (3)  
                 39 (2) 
                 −10 (3)  
               
               
                 C(24) 
                 61 (3) 
                 85 (4) 
                 46 (2) 
                 1 (2) 
                 30 (2) 
                 −7 (3) 
               
               
                 C(25) 
                 64 (3) 
                 73 (4) 
                 55 (2) 
                 3 (3) 
                 33 (2) 
                 −4 (3) 
               
               
                 C(22) 
                 66 (3) 
                 98 (4) 
                 49 (2) 
                 −8 (3)  
                 31 (2) 
                 −1 (3) 
               
               
                 C(26) 
                 95 (4) 
                 80 (4) 
                 75 (3) 
                 −13 (3)  
                 48 (3) 
                 −19 (3)  
               
               
                 C(21) 
                 122 (5)  
                 124 (6)  
                 75 (3) 
                 −26 (4)  
                 68 (3) 
                 −49 (5)  
               
               
                   
               
             
          
         
       
     
         [0000]    
       
         
               
             
               
               
               
               
               
             
               
               
               
               
               
               
             
           
               
                 TABLE 6 
               
             
             
               
                   
               
               
                 Hydrogen coordinates (Å 2  × 10 4 ) and isotropic displacement 
               
               
                 parameters (Å 2  × 10 3 ) for 24F2-DM. 
               
             
          
           
               
                   
                 x 
                 y 
                 z 
                 U(eq) 
               
               
                   
                   
               
             
          
           
               
                   
                 H(1A) 
                 7993 
                 6436 
                 9709 
                 98 
               
               
                   
                 H(2A) 
                 8012 
                 13327 
                 10455 
                 101 
               
               
                   
                 H(14A) 
                 8249 
                 15164 
                 6691 
                 60 
               
               
                   
                 H(3A) 
                 9039 
                 12019 
                 11341 
                 67 
               
               
                   
                 H(2B) 
                 8797 
                 8593 
                 10787 
                 66 
               
               
                   
                 H(2C) 
                 8143 
                 9613 
                 10650 
                 66 
               
               
                   
                 H(25A) 
                 8055 
                 11798 
                 1779 
                 113 
               
               
                   
                 H(4A) 
                 9440 
                 13693 
                 10577 
                 71 
               
               
                   
                 H(4B) 
                 9667 
                 11276 
                 10802 
                 71 
               
               
                   
                 H(10A) 
                 8964 
                 8360 
                 9604 
                 73 
               
               
                   
                 H(10B) 
                 8424 
                 9384 
                 8782 
                 73 
               
               
                   
                 H(11A) 
                 10056 
                 16104 
                 8096 
                 77 
               
               
                   
                 H(11B) 
                 9813 
                 18520 
                 7945 
                 77 
               
               
                   
                 H(1B) 
                 7826 
                 10546 
                 9341 
                 65 
               
               
                   
                 H(7A) 
                 8610 
                 11555 
                 8049 
                 62 
               
               
                   
                 H(6A) 
                 9297 
                 14334 
                 9379 
                 65 
               
               
                   
                 H(12A) 
                 9661 
                 16953 
                 6760 
                 68 
               
               
                   
                 H(12B) 
                 8984 
                 17711 
                 6630 
                 68 
               
               
                   
                 H(18A) 
                 9923 
                 12972 
                 6860 
                 82 
               
               
                   
                 H(18B) 
                 9447 
                 11287 
                 6895 
                 82 
               
               
                   
                 H(18C) 
                 9862 
                 12868 
                 7616 
                 82 
               
               
                   
                 H(15A) 
                 7797 
                 11855 
                 6468 
                 73 
               
               
                   
                 H(15B) 
                 8484 
                 10670 
                 6843 
                 73 
               
               
                   
                 H(17A) 
                 8321 
                 15218 
                 5536 
                 63 
               
               
                   
                 H(9A) 
                 9443 
                 16555 
                 8684 
                 77 
               
               
                   
                 H(9B) 
                 8860 
                 17610 
                 7905 
                 77 
               
               
                   
                 H(20A) 
                 9214 
                 12348 
                 5470 
                 69 
               
               
                   
                 H(27A) 
                 9385 
                 10090 
                 3436 
                 132 
               
               
                   
                 H(27B) 
                 9202 
                 8588 
                 2702 
                 132 
               
               
                   
                 H(27C) 
                 9104 
                 7759 
                 3387 
                 132 
               
               
                   
                 H(16A) 
                 7722 
                 12257 
                 5293 
                 76 
               
               
                   
                 H(16B) 
                 8331 
                 10685 
                 5618 
                 76 
               
               
                   
                 H(23A) 
                 8721 
                 13521 
                 3629 
                 81 
               
               
                   
                 H(23B) 
                 9079 
                 11576 
                 4216 
                 81 
               
               
                   
                 H(22A) 
                 8110 
                 11847 
                 4395 
                 85 
               
               
                   
                 H(22B) 
                 8102 
                 14250 
                 4132 
                 123 
               
               
                   
                 H(26A) 
                 7472 
                 8808 
                 1788 
                 123 
               
               
                   
                 H(26B) 
                 7913 
                 6956 
                 2373 
                 123 
               
               
                   
                 H(26C) 
                 8025 
                 7751 
                 1695 
                 123 
               
               
                   
                 H(21A) 
                 9629 
                 15868 
                 5799 
                 148 
               
               
                   
                 H(21B) 
                 9010 
                 16728 
                 5007 
                 148 
               
               
                   
                 H(21C) 
                 9511 
                 15179 
                 4964 
                 148 
               
               
                   
                   
               
             
          
         
       
     
         [0000]    
       
         
               
             
               
               
               
             
           
               
                 TABLE 7 
               
               
                   
               
               
                 Torsion angles [deg] for 24F2-DM. 
               
               
                   
               
             
             
               
                   
               
             
          
           
               
                   
                 C(18)—C(13)—C(14)—C(8) 
                 62.4(5) 
               
               
                   
                 C(17)—C(13)—C(14)—C(8) 
                 179.8(4) 
               
               
                   
                 C(12)—C(13)—C(14)—C(8) 
                 −58.1(5) 
               
               
                   
                 C(18)—C(13)—C(14)—C(15) 
                 −70.8(4) 
               
               
                   
                 C(17)—C(13)—C(14)—C(15) 
                 46.7(4) 
               
               
                   
                 C(12)—C(13)—C(14)—C(15) 
                 168.7(4) 
               
               
                   
                 O(2)—C(3)—C(2)—C(1) 
                 64.7(5) 
               
               
                   
                 C(4)—C(3)—C(2)—C(1) 
                 −54.8(5) 
               
               
                   
                 C(6)—C(5)—C(4)—C(3) 
                 130.9(5) 
               
               
                   
                 C(10)—C(5)—C(4)—C(3) 
                 −49.6(6) 
               
               
                   
                 O(2)—C(3)—C(4)—C(5) 
                 −71.4(5) 
               
               
                   
                 C(2)—C(3)—C(4)—C(5) 
                 49.9(6) 
               
               
                   
                 C(15)—C(14)—C(8)—C(7) 
                 −3.6(7) 
               
               
                   
                 C(13)—C(14)—C(8)—C(7) 
                 −128.4(5) 
               
               
                   
                 C(15)—C(14)—C(8)—C(9) 
                 179.7(4) 
               
               
                   
                 C(13)—C(14)—C(8)—C(9) 
                 54.9(5) 
               
               
                   
                 C(6)—C(5)—C(10)—C(1) 
                 −128.4(5) 
               
               
                   
                 C(4)—C(5)—C(10)—C(1) 
                 52.1(5) 
               
               
                   
                 C(3)—C(2)—C(1)—O(1) 
                 −175.9(4) 
               
               
                   
                 C(3)—C(2)—C(1)—C(10) 
                 59.1(6) 
               
               
                   
                 C(5)—C(10)—C(1)—O(1) 
                 178.8(3) 
               
               
                   
                 C(5)—C(10)—C(1)—C(2) 
                 −56.1(5) 
               
               
                   
                 C(14)—C(8)—C(7)—C(6) 
                 −176.5(4) 
               
               
                   
                 C(9)—C(8)—C(7)—C(6) 
                 −0.3(7) 
               
               
                   
                 C(4)—C(5)—C(6)—C(7) 
                 179.8(4) 
               
               
                   
                 C(10)—C(5)—C(6)—C(7) 
                 0.3(8) 
               
               
                   
                 C(8)—C(7)—C(6)—C(5) 
                 176.8(5) 
               
               
                   
                 C(9)—C(11)—C(12)—C(13) 
                 −56.0(6) 
               
               
                   
                 C(18)—C(13)—C(12)—C(11) 
                 −63.4(5) 
               
               
                   
                 C(17)—C(13)—C(12)—C(11) 
                 168.1(4) 
               
               
                   
                 C(14)—C(13)—C(12)—C(11) 
                 57.2(5) 
               
               
                   
                 C(8)—C(14)—C(15)—C(16) 
                 −164.9(4) 
               
               
                   
                 C(13)—C(14)—C(15)—C(16) 
                 −35.2(5) 
               
               
                   
                 C(18)—C(13)—C(17)—C(20) 
                 −48.2(6) 
               
               
                   
                 C(12)—C(13)—C(17)—C(20) 
                 80.1(5) 
               
               
                   
                 C(14)—C(13)—C(17)—C(20) 
                 −165.3(4) 
               
               
                   
                 C(18)—C(13)—C(17)—C(16) 
                 78.2(4) 
               
               
                   
                 C(12)—C(13)—C(17)—C(16) 
                 −153.6(4) 
               
               
                   
                 C(14)—C(13)—C(17)—C(16) 
                 −39.0(4) 
               
               
                   
                 C(7)—C(8)—C(9)—C(11) 
                 133.5(5) 
               
               
                   
                 C(14)—C(8)—C(9)—C(11) 
                 −49.9(5) 
               
               
                   
                 C(12)—C(11)—C(9)—C(8) 
                 51.1(6) 
               
               
                   
                 C(13)—C(17)—C(20)—C(21) 
                 −61.0(6) 
               
               
                   
                 C(16)—C(17)—C(20)—C(21) 
                 177.0(4) 
               
               
                   
                 C(13)—C(17)—C(20)—C(22) 
                 175.0(5) 
               
               
                   
                 C(16)—C(17)—C(20)—C(22) 
                 53.0(6) 
               
               
                   
                 C(14)—C(15)—C(16)—C(17) 
                 10.4(5) 
               
               
                   
                 C(13)—C(17)—C(16)—C(15) 
                 18.5(5) 
               
               
                   
                 C(20)—C(17)—C(16)—C(15) 
                 149.0(4) 
               
               
                   
                 C(22)—C(23)—C(24)—F(2) 
                 52.8(6) 
               
               
                   
                 C(22)—C(23)—C(24)—F(1) 
                 −60.0(6) 
               
               
                   
                 C(22)—C(23)—C(24)—C(25) 
                 177.5(5) 
               
               
                   
                 F(2)—C(24)—C(25)—O(25) 
                 61.0(5) 
               
               
                   
                 F(1)—C(24)—O(25)—O(25) 
                 173.2(4) 
               
               
                   
                 C(23)—C(24)—C(25)—O(25) 
                 −64.0(5) 
               
               
                   
                 F(2)—C(24)—C(25)—C(27) 
                 177.4(5) 
               
               
                   
                 F(1)—C(24)—C(25)—C(27) 
                 −70.4(6) 
               
               
                   
                 C(23)—C(24)—C(25)—C(27) 
                 52.4(7) 
               
               
                   
                 F(2)—C(24)—C(25)—C(26) 
                 −59.1(6) 
               
               
                   
                 F(1)—C(24)—C(25)—C(26) 
                 53.1(5) 
               
               
                   
                 C(23)—C(24)—C(25)—C(26) 
                 175.9(5) 
               
               
                   
                 C(24)—C(23)—C(22)—C(20) 
                 150.8(5) 
               
               
                   
                 C(21)—C(20)—C(22)—C(23) 
                 64.3(7) 
               
               
                   
                 C(17)—C(20)—C(22)—C(23) 
                 −170.9(5) 
               
               
                   
                   
               
             
          
         
       
     
         [0000]    
       
         
               
             
               
               
               
               
               
               
               
             
               
               
               
               
               
               
               
             
           
               
                 TABLE 8 
               
             
             
               
                   
               
               
                 Observed and calculated structure factors for 24F2-DM. 
               
             
          
           
               
                   
                 h 
                 k 
                 l 
                 10Fc 
                 10Fc 
                 10s 
               
               
                   
               
             
          
           
               
                   
                 1 
                 −7 
                 0 
                 41 
                 42 
                 4 
               
               
                   
                 3 
                 −7 
                 0 
                 38 
                 34 
                 6 
               
               
                   
                 0 
                 −6 
                 0 
                 53 
                 41 
                 8 
               
               
                   
                 2 
                 −6 
                 0 
                 43 
                 53 
                 10 
               
               
                   
                 4 
                 −6 
                 0 
                 11 
                 27 
                 10 
               
               
                   
                 6 
                 −6 
                 0 
                 63 
                 68 
                 4 
               
               
                   
                 10 
                 −6 
                 0 
                 0 
                 31 
                 1 
               
               
                   
                 1 
                 −5 
                 0 
                 65 
                 57 
                 6 
               
               
                   
                 3 
                 −5 
                 0 
                 310 
                 315 
                 8 
               
               
                   
                 5 
                 −5 
                 0 
                 131 
                 133 
                 8 
               
               
                   
                 7 
                 −5 
                 0 
                 143 
                 185 
                 7 
               
               
                   
                 9 
                 −5 
                 0 
                 23 
                 18 
                 23 
               
               
                   
                 11 
                 −5 
                 0 
                 36 
                 47 
                 8 
               
               
                   
                 13 
                 −5 
                 0 
                 91 
                 67 
                 10 
               
               
                   
                 15 
                 −5 
                 0 
                 82 
                 62  
                 10 
               
               
                   
                 0 
                 −4 
                 0 
                 683 
                 673 
                 48 
               
               
                   
                 2 
                 −4 
                 0 
                 87 
                 87 
                 4 
               
               
                   
                 4 
                 −4 
                 0 
                 282 
                 277 
                 6 
               
               
                   
                 6 
                 −4 
                 0 
                 31 
                 27 
                 8 
               
               
                   
                 8 
                 −4 
                 0 
                 0 
                 13 
                 1 
               
               
                   
                 10 
                 −4 
                 0 
                 59 
                 60 
                 8 
               
               
                   
                 12 
                 −4 
                 0 
                 81 
                 99 
                 10 
               
               
                   
                 14 
                 −4 
                 0 
                 14 
                 30 
                 14 
               
               
                   
                 16 
                 −4 
                 0 
                 64 
                 55 
                 5 
               
               
                   
                 18 
                 −4 
                 0 
                 55 
                 51 
                 16 
               
               
                   
                 1 
                 −3 
                 0 
                 313 
                 323 
                 15 
               
               
                   
                 3 
                 −3 
                 0 
                 73 
                 82 
                 5 
               
               
                   
                 7 
                 −3 
                 0 
                 185 
                 179 
                 6 
               
               
                   
                 9 
                 −3 
                 0 
                 258 
                 262 
                 7 
               
               
                   
                 11 
                 −3 
                 0 
                 211 
                 177 
                 6 
               
               
                   
                 13 
                 −3 
                 0 
                 88 
                 89 
                 6 
               
               
                   
                 15 
                 −3 
                 0 
                 55 
                 68 
                 7 
               
               
                   
                 17 
                 −3 
                 0 
                 78 
                 92 
                 5 
               
               
                   
                 19 
                 −3 
                 0 
                 71 
                 65 
                 6 
               
               
                   
                 21 
                 −3 
                 0 
                 28  
                 28 
                 8 
               
               
                   
                 0 
                 −2 
                 0 
                 1114 
                 1129 
                 40 
               
               
                   
                 2 
                 −2 
                 0 
                 208 
                 206 
                 13 
               
               
                   
                 4 
                 −2 
                 0 
                 795 
                 756 
                 34 
               
               
                   
                 6 
                 −2 
                 0 
                 512 
                 529 
                 28 
               
               
                   
                 8 
                 −2 
                 0 
                 210 
                 179 
                 11 
               
               
                   
                 10 
                 −2 
                 0 
                 246 
                 231 
                 8 
               
               
                   
                 12 
                 −2 
                 0 
                 174 
                 177 
                 6 
               
               
                   
                 14 
                 −2 
                 0 
                 85 
                 84 
                 5 
               
               
                   
                 16 
                 −2 
                 0 
                 87 
                 99 
                 7 
               
               
                   
                 18 
                 −2 
                 0 
                 41 
                 48 
                 14 
               
               
                   
                 20 
                 −2 
                 0 
                 114 
                 102 
                 8 
               
               
                   
                 22 
                 −2 
                 0 
                 31 
                 33 
                 14 
               
               
                   
                 1 
                 −1 
                 0 
                 1222  
                 1167 
                 35 
               
               
                   
                 3 
                 −1 
                 0 
                 1786 
                 1655 
                 83 
               
               
                   
                 5 
                 −1 
                 0 
                 1028 
                 1026 
                 42 
               
               
                   
                 7 
                 −1 
                 0 
                 657 
                 823 
                 39 
               
               
                   
                 9 
                 −1 
                 0 
                 202 
                 252 
                 11 
               
               
                   
                 11 
                 −1 
                 0 
                 128 
                 136 
                 10 
               
               
                   
                 13 
                 −1 
                 0 
                 46 
                 36 
                 12 
               
               
                   
                 15 
                 −1 
                 0 
                 225 
                 216 
                 7 
               
               
                   
                 17 
                 −1 
                 0 
                 149 
                 139 
                 5 
               
               
                   
                 19 
                 −1 
                 0 
                 41 
                 51 
                 17 
               
               
                   
                 21 
                 −1 
                 0 
                 42 
                 40 
                 14 
               
               
                   
                 2 
                 0 
                 0 
                 866 
                 876 
                 44 
               
               
                   
                 4 
                 0 
                 0 
                 2245 
                 2228 
                 115 
               
               
                   
                 6 
                 0 
                 0 
                 185 
                 242 
                 10 
               
               
                   
                 8 
                 0 
                 0 
                 305 
                 354 
                 16 
               
               
                   
                 10 
                 0 
                 0 
                 38 
                 24 
                 21 
               
               
                   
                 12 
                 0 
                 0 
                 306 
                 301 
                 11 
               
               
                   
                 14 
                 0 
                 0 
                 213 
                 215 
                 6 
               
               
                   
                 16 
                 0 
                 0 
                 62 
                 62 
                 15 
               
               
                   
                 18 
                 0 
                 0 
                 0 
                 5 
                 1 
               
               
                   
                 20 
                 0 
                 0 
                 27 
                 30 
                 26 
               
               
                   
                 1 
                 1 
                 0 
                 1218 
                 1167 
                 63 
               
               
                   
                 3 
                 1 
                 0 
                 1655 
                 1656 
                 94 
               
               
                   
                 5 
                 1 
                 0 
                 989 
                 1026 
                 55 
               
               
                   
                 9 
                 1 
                 0 
                 210 
                 231 
                 11 
               
               
                   
                 11 
                 1 
                 0 
                 138 
                 136 
                 11 
               
               
                   
                 13 
                 1 
                 0 
                 35 
                 36 
                 29 
               
               
                   
                 15 
                 1 
                 0 
                 219 
                 216 
                 11 
               
               
                   
                 17 
                 1 
                 0 
                 126 
                 140 
                 10 
               
               
                   
                 19 
                 1 
                 0 
                 39 
                 51 
                 32 
               
               
                   
                 21 
                 1 
                 0 
                 53 
                 41 
                 16 
               
               
                   
                 2 
                 2 
                 0 
                 224 
                 209 
                 11 
               
               
                   
                 4 
                 2 
                 0 
                 758 
                 755 
                 41 
               
               
                   
                 6 
                 2 
                 0 
                 550 
                 532 
                 26 
               
               
                   
                 8 
                 2 
                 0 
                 204 
                 180 
                 12 
               
               
                   
                 10 
                 2 
                 0 
                 242 
                 328 
                 14 
               
               
                   
                 12 
                 2 
                 0 
                 183 
                 176 
                 13 
               
               
                   
                 14 
                 2 
                 0 
                 91 
                 84 
                 12 
               
               
                   
                 16 
                 2 
                 0 
                 89 
                 99 
                 12 
               
               
                   
                 18 
                 2 
                 0 
                 44 
                 47 
                 25 
               
               
                   
                 −6 
                 2 
                 2 
                 749 
                 742 
                 35 
               
               
                   
                 −4 
                 2 
                 2 
                 169 
                 161 
                 9 
               
               
                   
                 −2 
                 2 
                 2 
                 211 
                 214 
                 9 
               
               
                   
                 0 
                 2 
                 2 
                 489 
                 463 
                 25 
               
               
                   
                 2 
                 2 
                 2 
                 576 
                 530 
                 25 
               
               
                   
                 4 
                 2 
                 2 
                 467 
                 442 
                 24 
               
               
                   
                 6 
                 2 
                 2 
                 234 
                 218 
                 13 
               
               
                   
                 8 
                 2 
                 2 
                 170 
                 152 
                 13 
               
               
                   
                 10 
                 2 
                 2 
                 142 
                 130 
                 7 
               
               
                   
                 12 
                 2 
                 2 
                 209 
                 212 
                 13 
               
               
                   
                 14 
                 2 
                 2 
                 104 
                 96 
                 10 
               
               
                   
                 16 
                 2 
                 2 
                 100 
                 107 
                 10 
               
               
                   
                 20 
                 2 
                 2 
                 49 
                 49 
                 15 
               
               
                   
                 −21 
                 3 
                 2 
                 18 
                 33 
                 18 
               
               
                   
                 −19 
                 3 
                 2 
                 178 
                 160 
                 12 
               
               
                   
                 −17 
                 3 
                 2 
                 65 
                 59 
                 17 
               
               
                   
                 −15 
                 3 
                 2 
                 153 
                 162 
                 10 
               
               
                   
                 −13 
                 3 
                 2 
                 101 
                 125 
                 12 
               
               
                   
                 9 
                 3 
                 2 
                 189 
                 167 
                 11 
               
               
                   
                 11 
                 3 
                 2 
                 93 
                 78 
                 11 
               
               
                   
                 13 
                 3 
                 2 
                 0 
                 30 
                 1 
               
               
                   
                 15 
                 3 
                 2 
                 41 
                 64 
                 35 
               
               
                   
                 19 
                 3 
                 2 
                 43 
                 35 
                 20 
               
               
                   
                 16 
                 4 
                 2 
                 41 
                 37 
                 26 
               
               
                   
                 −3 
                 −7 
                 3 
                 41 
                 44 
                 4 
               
               
                   
                 −1 
                 −7 
                 3 
                 20 
                 15 
                 20 
               
               
                   
                 −12 
                 −6 
                 3 
                 44 
                 44 
                 6 
               
               
                   
                 −10 
                 −6 
                 3 
                 34 
                 29 
                 9 
               
               
                   
                 −8 
                 −6 
                 3 
                 30 
                 19 
                 11 
               
               
                   
                 −6 
                 −6 
                 3 
                 57 
                 59 
                 5 
               
               
                   
                 −4 
                 −6 
                 3 
                 84 
                 79 
                 4 
               
               
                   
                 −2 
                 −6 
                 3 
                 80 
                 81 
                 4 
               
               
                   
                 0 
                 −6 
                 3 
                 70 
                 69 
                 4 
               
               
                   
                 2 
                 −6 
                 3 
                 19 
                 13 
                 18 
               
               
                   
                 4 
                 −6 
                 3 
                 25 
                 28 
                 24 
               
               
                   
                 6 
                 −6 
                 3 
                 0 
                 18 
                 1 
               
               
                   
                 8 
                 −6 
                 3 
                 0 
                 15 
                 1 
               
               
                   
                 −17 
                 −5 
                 3 
                 28 
                 24 
                 10 
               
               
                   
                 −15 
                 −5 
                 3 
                 39 
                 35 
                 9 
               
               
                   
                 −13 
                 −5 
                 3 
                 50 
                 64 
                 7 
               
               
                   
                 −11 
                 −5 
                 3 
                 66 
                 72 
                 20 
               
               
                   
                 −9 
                 −5 
                 3 
                 87 
                 82 
                 7 
               
               
                   
                 −7 
                 −5 
                 3 
                 288 
                 270 
                 8 
               
               
                   
                 −5 
                 −5 
                 3 
                 155 
                 129 
                 9 
               
               
                   
                 −3 
                 −5 
                 3 
                 106 
                 88 
                 7 
               
               
                   
                 −1 
                 −5 
                 3 
                 156 
                 154 
                 5 
               
               
                   
                 1 
                 −5 
                 3 
                 153 
                 160 
                 6 
               
               
                   
                 3 
                 −5 
                 3 
                 162 
                 160 
                 6 
               
               
                   
                 5 
                 −5 
                 3 
                 75 
                 69 
                 10 
               
               
                   
                 7 
                 −5 
                 3 
                 78 
                 93 
                 10 
               
               
                   
                 9 
                 −5 
                 3 
                 1 
                 48 
                 1 
               
               
                   
                 11 
                 −5 
                 3 
                 27 
                 8 
                 27 
               
               
                   
                 13 
                 −5 
                 3 
                 22 
                 9 
                 22 
               
               
                   
                 −20 
                 −4 
                 3 
                 35 
                 23 
                 10 
               
               
                   
                 −18 
                 −4 
                 3 
                 0 
                 24 
                 1 
               
               
                   
                 −16 
                 −4 
                 3 
                 59 
                 75 
                 13 
               
               
                   
                 −14 
                 −4 
                 3 
                 103 
                 134 
                 12 
               
               
                   
                 −12 
                 −4 
                 3 
                 33 
                 32 
                 14 
               
               
                   
                 −10 
                 −4 
                 3 
                 83 
                 82 
                 5 
               
               
                   
                 −8 
                 −4 
                 3 
                 140 
                 136 
                 4 
               
               
                   
                 −6 
                 −4 
                 3 
                 104 
                 102 
                 3 
               
               
                   
                 −4 
                 −4 
                 3 
                 470 
                 447 
                 9 
               
               
                   
                 −2 
                 −4 
                 3 
                 140 
                 128 
                 3 
               
               
                   
                 0 
                 −4 
                 3 
                 329 
                 319 
                 8 
               
               
                   
                 2 
                 −4 
                 3 
                 83  
                 78 
                 4 
               
               
                   
                 4 
                 −4 
                 3 
                 209 
                 203 
                 6 
               
               
                   
                 6 
                 −4 
                 3 
                 209 
                 203 
                 9 
               
               
                   
                 8 
                 −4 
                 3 
                 139 
                 143 
                 9 
               
               
                   
                 10 
                 −4 
                 3 
                 111 
                 120 
                 10 
               
               
                   
                 12 
                 −4 
                 3 
                 0 
                 46 
                 1 
               
               
                   
                 14 
                 −4 
                 3 
                 28 
                 21 
                 27 
               
               
                   
                 16 
                 −4 
                 3 
                 27 
                 40 
                 27 
               
               
                   
                 −21 
                 −3 
                 3 
                 53 
                 52 
                 8 
               
               
                   
                 −19 
                 −3 
                 3 
                 66 
                 60 
                 7 
               
               
                   
                 −17 
                 −3 
                 3 
                 54 
                 12 
                 16 
               
               
                   
                 −15 
                 −3 
                 3 
                 95 
                 92 
                 5 
               
               
                   
                 −13 
                 −3 
                 3 
                 51 
                 62 
                 7 
               
               
                   
                 −11 
                 −3 
                 3 
                 73 
                 77 
                 6 
               
               
                   
                 −9 
                 −3 
                 3 
                 3 
                 329 
                 7 
               
               
                   
                 −7 
                 −3 
                 3 
                 191 
                 185 
                 11 
               
               
                   
                 −5 
                 −3 
                 3 
                 213 
                 213 
                 12 
               
               
                   
                 −3 
                 −3 
                 3 
                 169 
                 199 
                 10 
               
               
                   
                 −1 
                 −3 
                 3 
                 309 
                 290 
                 16 
               
               
                   
                 1 
                 −3 
                 3 
                 155 
                 167 
                 11 
               
               
                   
                 3 
                 −3 
                 3 
                 258 
                 237 
                 15 
               
               
                   
                 5 
                 −3 
                 3 
                 406 
                 389 
                 14 
               
               
                   
                 7 
                 −3 
                 3 
                 264 
                 260 
                 7 
               
               
                   
                 −7 
                 −3 
                 5 
                 281 
                 266 
                 10 
               
               
                   
                 −5 
                 −3 
                 5 
                 242 
                 228 
                 13 
               
               
                   
                 −3 
                 −3 
                 5 
                 289 
                 263 
                 10 
               
               
                   
                 −1 
                 −3 
                 5 
                 229 
                 180 
                 13 
               
               
                   
                 1 
                 −3 
                 5 
                 131 
                 106 
                 12 
               
               
                   
                 3 
                 −3 
                 5 
                 268 
                 265 
                 10 
               
               
                   
                 5 
                 −3 
                 5 
                 218 
                 195 
                 8 
               
               
                   
                 7 
                 −3 
                 5 
                 119 
                 121 
                 9 
               
               
                   
                 9 
                 −3 
                 5 
                 98 
                 80 
                 10 
               
               
                   
                 11 
                 −3 
                 5 
                 92 
                 91 
                 5 
               
               
                   
                 13 
                 −3 
                 5 
                 47 
                 28 
                 8 
               
               
                   
                 −24 
                 −2 
                 5 
                 60 
                 50 
                 8 
               
               
                   
                 −22 
                 −2 
                 5 
                 51 
                 61 
                 10 
               
               
                   
                 −20 
                 −2 
                 5 
                 150 
                 133 
                 5 
               
               
                   
                 −18 
                 −2 
                 5 
                 355 
                 342 
                 9 
               
               
                   
                 −16 
                 −2 
                 5 
                 268 
                 264 
                 7 
               
               
                   
                 −14 
                 −2 
                 5 
                 386 
                 397 
                 8 
               
               
                   
                 −12 
                 −2 
                 5 
                 117 
                 119 
                 5 
               
               
                   
                 −10 
                 −2 
                 5 
                 72 
                 33 
                 11 
               
               
                   
                 −8 
                 −2 
                 5 
                 252 
                 257 
                 14 
               
               
                   
                 −6 
                 −2 
                 5 
                 352 
                 405 
                 18 
               
               
                   
                 −4 
                 −2 
                 5 
                 451 
                 472 
                 25 
               
               
                   
                 −2 
                 −2 
                 5 
                 447 
                 420 
                 22 
               
               
                   
                 0 
                 −2 
                 5 
                 309 
                 277 
                 16 
               
               
                   
                 2 
                 −2 
                 5 
                 514 
                 461 
                 25 
               
               
                   
                 4 
                 −2 
                 5 
                 377 
                 363 
                 20 
               
               
                   
                 6 
                 −2 
                 5 
                 177 
                 197 
                 8 
               
               
                   
                 8 
                 −2 
                 5 
                 0 
                 31 
                 1 
               
               
                   
                 10 
                 −2 
                 5 
                 164 
                 167 
                 8 
               
               
                   
                 12 
                 −2 
                 5 
                 36 
                 53 
                 12 
               
               
                   
                 14 
                 −2 
                 5 
                 66 
                 77 
                 7 
               
               
                   
                 16 
                 −2 
                 5 
                 87 
                 90 
                 6 
               
               
                   
                 18 
                 −2 
                 5 
                 61 
                 78 
                 5 
               
               
                   
                 −23 
                 −1 
                 5 
                 140 
                 113 
                 10 
               
               
                   
                 −21 
                 −1 
                 5 
                 89 
                 84 
                 10 
               
               
                   
                 −19 
                 −1 
                 5 
                 102 
                 99 
                 10 
               
               
                   
                 −17 
                 −1 
                 5 
                 82 
                 97 
                 8 
               
               
                   
                 −15 
                 −1 
                 5 
                 188 
                 189 
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                 −21 
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                 1 
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                 0 
                 2 
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                 28 
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                 28 
               
               
                   
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                 88 
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                 0 
                 23 
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                 16 
                 0 
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                 1 
               
               
                   
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                 40 
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                 3 
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                 0 
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                 0 
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                 22 
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                 50 
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                 20 
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                 32 
               
               
                   
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                 0 
                 15 
                 1 
               
               
                   
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                 3 
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                 12 
                 16 
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                 0 
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                 19 
                 9 
               
               
                   
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                 25 
                 11 
               
               
                   
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                 17 
                 4 
                 17 
               
               
                   
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                 21 
                 26 
                 23 
                 26 
               
               
                   
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                 −7 
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                 40 
                 35 
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                 4 
                 25 
               
               
                   
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                 10 
                 25 
               
               
                   
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                 0 
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                 1 
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                 0 
                 21 
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                 0 
                 21 
                 41 
                 46 
                 12 
               
               
                   
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                 0 
                 21 
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                 0 
                 21 
                 20 
                 16 
                 20 
               
               
                   
                 −6 
                 0 
                 21 
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                 9 
                 14 
               
               
                   
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                 1 
                 21 
                 44 
                 33 
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                 1 
                 21 
                 36 
                 46 
                 20 
               
               
                   
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                 1 
                 21 
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                 59 
                 7 
               
               
                   
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                 1 
                 21 
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                 6 
               
               
                   
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                 1 
                 21 
                 50 
                 54 
                 10 
               
               
                   
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                 1 
                 21 
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                 1 
                 21 
                 44 
                 30 
                 10 
               
               
                   
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                 1 
                 21 
                 27 
                 35 
                 27 
               
               
                   
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                 2 
                 21 
                 27 
                 32 
                 26 
               
               
                   
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                 21 
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                 37 
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                 2 
                 21 
                 0 
                 18 
                 1 
               
               
                   
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                 2 
                 21 
                 23 
                 25 
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                 2 
                 21 
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                 4 
                 1 
               
               
                   
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                 2 
                 21 
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                 23 
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                 0 
                 22 
                 16 
                 31 
                 16 
               
               
                   
                 −16 
                 0 
                 22 
                 40 
                 40 
                 40 
               
               
                   
                 −14 
                 0 
                 22 
                 29 
                 7 
                 28 
               
               
                   
                 −17 
                 1 
                 22 
                 33 
                 31 
                 14 
               
               
                   
                 −15 
                 1 
                 22 
                 68 
                 34 
                 10 
               
               
                   
                 −13 
                 1 
                 22 
                 86 
                 76 
                 6 
               
               
                   
                 −11 
                 1 
                 22 
                 68 
                 71 
                 8 
               
               
                   
               
             
          
         
       
     
       REFERENCES 
       [0000]    
       
         1. CrysAlis RED, Oxford Diffraction Ltd., Version 1.171.28 cycle2 beta (release 25-10-2005 CrysAlis171.NET) (compiled Oct. 25 2005, 08:50:05). Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm. 
         2. CrysAlis CCD, Oxford Diffraction Ltd., Version 1.171.28 cycle2 beta; CrysAlis RED, Oxford Diffraction Ltd., Version 1.171.28 cycle2 beta. 
         3. G. M. Sheidrick, Acta Crystallogr. 1990, A46, 467-473. 
         4. G. M. Sheldrick, SHELXL93 . Program for the Reminement of Crystal Structures , Univ. of Götttingen, Germany. 
         5 . International Tables for Crystallography , Ed. A. J. C. Wilson, Kluwer:Dordrecth, 1992, Vol. C. 
       
     
       Example 2 
     Synthesis of 24F2-DM 
       [0032]    The preparation of 24F2-DM 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 I (24F2-DM). 
         [0000]    
       
                 
         
             
             
         
       
     
         [0033]    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. 
         [0034]    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. 5,086,191 which are hereby incorporated by reference in their entirety as if fully set forth herein. 
         [0035]    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.