Synthesis of Highly Substituted Cryptophane Derivatives
Thierry Brotin; Dominique Cavagnat; Erwann Jeanneau; Thierry Buffeteau; Journal of Organic Chemistry 78 (2013) 6143–6153; doi:10.1021/jo4007738

data_4028356
_publ_section_title
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 Synthesis of Highly Substituted Cryptophane Derivatives
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_journal_name_full               'Journal of Organic Chemistry'
_journal_page_first              6143
_journal_page_last               6153
_journal_paper_doi               10.1021/jo4007738
_journal_volume                  78
_journal_year                    2013
_chemical_formula_moiety         'C57 H60 O15, C H2 Cl2'
_chemical_formula_sum            'C58 H62 Cl2 O15'
_chemical_formula_weight         1069.98
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 1 21/c 1'
_atom_sites_solution_hydrogens   difmap
_atom_sites_solution_primary     direct
_cell_angle_alpha                90
_cell_angle_beta                 90.932(2)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   18.7181(4)
_cell_length_b                   12.5131(3)
_cell_length_c                   21.9113(6)
_cell_measurement_reflns_used    11941
_cell_measurement_temperature    100
_cell_measurement_theta_max      66.7906
_cell_measurement_theta_min      3.1278
_cell_volume                     5131.4(2)
_computing_cell_refinement
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.20 (release 27-06-2012 CrysAlis171 .NET)
(compiled Jul 11 2012,15:38:31)
;
_computing_data_collection
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.20 (release 27-06-2012 CrysAlis171 .NET)
(compiled Jul 11 2012,15:38:31)
;
_computing_data_reduction
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.20 (release 27-06-2012 CrysAlis171 .NET)
(compiled Jul 11 2012,15:38:31)
;
_computing_molecular_graphics    'CAMERON (Watkin et al., 1996)'
_computing_publication_material  'CRYSTALS (Betteridge et al., 2003)'
_computing_structure_refinement  'CRYSTALS (Betteridge et al., 2003)'
_computing_structure_solution    'SIR97 (Altomare et al., 1999)'
_diffrn_ambient_temperature      100
_diffrn_detector_area_resol_mean 10.4678
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measurement_device_type  'Xcalibur, Atlas, Gemini ultra'
_diffrn_measurement_method       \w
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_source         'Enhance Ultra (Cu) x-ray Source'
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.5418
_diffrn_reflns_av_R_equivalents  0.059
_diffrn_reflns_limit_h_max       22
_diffrn_reflns_limit_h_min       -22
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_limit_l_min       -26
_diffrn_reflns_number            42909
_diffrn_reflns_theta_full        66.759
_diffrn_reflns_theta_max         66.898
_diffrn_reflns_theta_min         4.036
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    1.738
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.72187
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.20 (release 27-06-2012 CrysAlis171 .NET)
(compiled Jul 11 2012,15:38:31)
empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.385
_exptl_crystal_description       block
_exptl_crystal_F_000             2256.000
_exptl_crystal_size_max          0.215
_exptl_crystal_size_mid          0.199
_exptl_crystal_size_min          0.126
_refine_diff_density_max         0.88
_refine_diff_density_min         -1.87
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.0159
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     703
_refine_ls_number_reflns         9080
_refine_ls_number_restraints     19
_refine_ls_R_factor_all          0.0931
_refine_ls_R_factor_gt           0.0783
_refine_ls_shift/su_max          0.0052286
_refine_ls_shift/su_mean         0.0006324
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
;
 Method, part 1, Chebychev polynomial, (Watkin, 1994, Prince, 1982) 
 [weight] = 1.0/[A~0~*T~0~(x)+A~1~*T~1~(x) ... +A~n-1~]*T~n-1~(x)] 
 where A~i~ are the Chebychev coefficients listed below and x= Fcalc/Fmax 
 Method = Robust Weighting (Prince, 1982) 
 W = [weight] * [1-(deltaF/6*sigmaF)^2^]^2^ 
 A~i~ are: 
 0.334E+04 0.563E+04 0.351E+04 0.149E+04 341. 
;
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_all         0.2487
_refine_ls_wR_factor_gt          0.2186
_refine_ls_wR_factor_ref         0.2487
_reflns_limit_h_max              22
_reflns_limit_h_min              -22
_reflns_limit_k_max              14
_reflns_limit_k_min              0
_reflns_limit_l_max              26
_reflns_limit_l_min              0
_reflns_number_gt                7167
_reflns_number_total             9080
_reflns_threshold_expression     I>2.0\s(I)
_oxford_diffrn_Wilson_B_factor   2.96
_oxford_diffrn_Wilson_scale      0.12
_oxford_refine_ls_r_factor_ref   0.0931
_oxford_refine_ls_scale          2.67(4)
_oxford_reflns_number_all        9080
_oxford_reflns_threshold_expression_ref I>-10.0\s(I)
_cod_data_source_file            jo4007738_si_001_5.cif
_cod_data_source_block           4
_cod_original_sg_symbol_H-M      'P 1 21/c 1 '
_cod_database_code               4028356
_iucr_refine_instruction_details_constraints
;
BLOCK SCALE X'S, U'S 
RIDE C   (   2,X'S) H   (  23,X'S) H   (  24,X'S)  H   (  21,X'S) H   (  22,X'S)
 
RIDE C   (   6,X'S) H   (  61,X'S) H   (  63,X'S) H   (  62,X'S) 
RIDE C   (   9,X'S) H   (  92,X'S) H   (  91,X'S) 
RIDE C   (  12,X'S) H   ( 122,X'S) H   ( 121,X'S) 
RIDE C   (  17,X'S) H   ( 171,X'S) H   ( 173,X'S) H   ( 172,X'S) 
RIDE C   (  20,X'S) H   ( 201,X'S) H   ( 202,X'S) 
RIDE C   (  21,X'S) H   ( 211,X'S) H   ( 212,X'S) 
RIDE C   (  24,X'S) H   ( 241,X'S) 
RIDE C   (  26,X'S) H   ( 261,X'S) H   ( 262,X'S) 
RIDE C   (  28,X'S) H   ( 281,X'S) 
RIDE C   (  31,X'S) H   ( 311,X'S) H   ( 312,X'S) H   ( 313,X'S) 
RIDE C   (  34,X'S) H   ( 341,X'S) H   ( 342,X'S) 
RIDE C   (  35,X'S) H   ( 351,X'S) H   ( 352,X'S) 
RIDE C   (  36,X'S) H   ( 361,X'S) H   ( 362,X'S) 
RIDE C   (  37,X'S) H   ( 371,X'S) H   ( 372,X'S) 
RIDE C   (  42,X'S) H   ( 421,X'S) H   ( 422,X'S) H   ( 423,X'S) 
RIDE C   (  44,X'S) H   ( 441,X'S) 
RIDE C   (  46,X'S) H   ( 461,X'S) H   ( 462,X'S) H   ( 463,X'S) 
RIDE C   (  47,X'S) H   ( 471,X'S) 
RIDE C   (  49,X'S) H   ( 491,X'S) H   ( 492,X'S) 
RIDE C   (  52,X'S) H   ( 521,X'S) H   ( 522,X'S) 
RIDE C   (  54,X'S) H   ( 541,X'S) 
RIDE C   (  57,X'S) H   ( 571,X'S) H   ( 572,X'S) H   ( 573,X'S) 
RIDE C   (  58,X'S) H   ( 581,X'S) 
RIDE C   (  61,X'S) H   ( 611,X'S) H   ( 612,X'S) 
RIDE C   (  62,X'S) H   ( 621,X'S) H   ( 622,X'S) 
RIDE C   (  67,X'S) H   ( 671,X'S) H   ( 672,X'S) H   ( 673,X'S) 
RIDE C   (  68,X'S) H   ( 681,X'S) 
RIDE C   (  70,X'S) H   ( 701,X'S) H   ( 702,X'S) 
RIDE C   (  72,X'S) H   ( 721,X'S) 
RIDE C   (  74,X'S) H   ( 742,X'S) H   ( 741,X'S) H   ( 743,X'S) 
RIDE C   (  76,X'S) H   ( 761,X'S) 
RIDE C   (  78,X'S) H   ( 783,X'S) H   ( 782,X'S) H   ( 781,X'S) 
END                                                                             
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_iucr_refine_instruction_details_restraints
;
NO 
REM   HREST   START (DO NOT REMOVE THIS LINE) 
REM   HREST   END (DO NOT REMOVE THIS LINE) 
U(IJ)'S  0.0, 0.0050000 = C(37) TO C(34) 
U(IJ)'S  0.0, 0.0050000 = C(35) TO C(36) 
DISTANCE 1.500000 , 0.010000 = C(35) TO C(37) 
U(IJ)'S  0.0, 0.005000 = CL(3) TO CL(5) 
END                                                                             
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