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_4028354
_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         'C60 H63 Cl9 O15'
_chemical_formula_sum            'C60 H63 Cl9 O15'
_chemical_formula_weight         1343.22
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2yn'
_symmetry_space_group_name_H-M   'P 1 21/n 1'
_atom_sites_solution_hydrogens   difmap
_atom_sites_solution_primary     direct
_cell_angle_alpha                90
_cell_angle_beta                 102.3363(8)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   21.2637(2)
_cell_length_b                   13.10460(10)
_cell_length_c                   21.9793(2)
_cell_measurement_reflns_used    32491
_cell_measurement_temperature    100
_cell_measurement_theta_max      66.7733
_cell_measurement_theta_min      3.2582
_cell_volume                     5983.17(9)
_computing_cell_refinement
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.21c (release 23-05-2012 CrysAlis171 .NET)
(compiled May 23 2012,12:53:54)
;
_computing_data_collection
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.21c (release 23-05-2012 CrysAlis171 .NET)
(compiled May 23 2012,12:53:54)
;
_computing_data_reduction
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.21c (release 23-05-2012 CrysAlis171 .NET)
(compiled May 23 2012,12:53:54)
;
_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 0.995
_diffrn_measured_fraction_theta_max 0.995
_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  0.035
_diffrn_reflns_limit_h_max       21
_diffrn_reflns_limit_h_min       -25
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       26
_diffrn_reflns_limit_l_min       -25
_diffrn_reflns_number            67563
_diffrn_reflns_theta_full        66.881
_diffrn_reflns_theta_max         66.881
_diffrn_reflns_theta_min         3.261
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    4.423
_exptl_absorpt_correction_T_max  0.492
_exptl_absorpt_correction_T_min  0.157
_exptl_absorpt_correction_type   analytical
_exptl_absorpt_process_details
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.21c (release 23-05-2012 CrysAlis171 .NET)
(compiled May 23 2012,12:53:54)
Analytical numeric absorption correction using a multifaceted crystal
            model based on expressions derived by R.C. Clark & J.S. Reid.
(Clark, R. C. & Reid, J. S. (1995). Acta Cryst. A51, 887-897)
;
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.491
_exptl_crystal_description       plate
_exptl_crystal_F_000             2784
_exptl_crystal_size_max          0.602
_exptl_crystal_size_mid          0.419
_exptl_crystal_size_min          0.191
_refine_diff_density_max         1.47
_refine_diff_density_min         -1.32
_refine_ls_extinction_coef       18(3)
_refine_ls_extinction_method     'Larson (1970), Equation 22'
_refine_ls_goodness_of_fit_ref   0.9885
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     785
_refine_ls_number_reflns         10596
_refine_ls_number_restraints     19
_refine_ls_R_factor_all          0.0569
_refine_ls_R_factor_gt           0.0543
_refine_ls_shift/su_max          0.0006034
_refine_ls_shift/su_mean         0.0000325
_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: 
 0.223E+04 0.375E+04 0.229E+04 941. 210. 
;
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_all         0.1514
_refine_ls_wR_factor_gt          0.1485
_refine_ls_wR_factor_ref         0.1514
_reflns_limit_h_max              24
_reflns_limit_h_min              -25
_reflns_limit_k_max              15
_reflns_limit_k_min              0
_reflns_limit_l_max              26
_reflns_limit_l_min              0
_reflns_number_gt                9820
_reflns_number_total             10596
_reflns_threshold_expression     I>2.0\s(I)
_oxford_diffrn_Wilson_B_factor   3.51
_oxford_diffrn_Wilson_scale      0.09
_oxford_refine_ls_r_factor_ref   0.0569
_oxford_refine_ls_scale          1.895(12)
_oxford_reflns_number_all        10596
_oxford_reflns_threshold_expression_ref I>-10.0\s(I)
_cod_data_source_file            jo4007738_si_001_3.cif
_cod_data_source_block           2
_cod_original_sg_symbol_H-M      'P 21/n '
_cod_database_code               4028354
_iucr_refine_instruction_details_constraints
;
BLOCK SCALE X'S, U'S 
CONT EXTPARAM 
RIDE C   (   2,X'S) H   (  21,X'S) 
RIDE C   (   3,X'S) H   (  31,X'S) 
RIDE C   (   7,X'S) H   (  71,X'S) 
RIDE C   (  11,X'S) H   ( 111,X'S) 
RIDE C   (  18,X'S) H   ( 181,X'S) H   ( 182,X'S) 
RIDE C   (  21,X'S) H   ( 211,X'S) 
RIDE C   (  24,X'S) H   ( 243,X'S) H   ( 242,X'S) H   ( 241,X'S) 
RIDE C   (  28,X'S) H   ( 282,X'S) H   ( 281,X'S) H   ( 283,X'S) 
RIDE C   (  30,X'S) H   ( 301,X'S) H   ( 302,X'S) 
RIDE C   (  31,X'S) H   ( 311,X'S) H   ( 312,X'S) 
RIDE C   (  36,X'S) H   ( 363,X'S) H   ( 362,X'S) H   ( 361,X'S) 
RIDE C   (  37,X'S) H   ( 371,X'S) 
RIDE C   (  39,X'S) H   ( 392,X'S) H   ( 391,X'S) 
RIDE C   (  42,X'S) H   ( 421,X'S) H   ( 422,X'S) 
RIDE C   (  45,X'S) H   ( 451,X'S) 
RIDE C   (  48,X'S) H   ( 483,X'S) H   ( 481,X'S) H   ( 482,X'S) 
RIDE C   (  50,X'S) H   ( 501,X'S) 
RIDE C   (  52,X'S) H   ( 521,X'S) H   ( 522,X'S) 
RIDE C   (  53,X'S) H   ( 531,X'S) H   ( 532,X'S) 
RIDE C   (  57,X'S) H   ( 571,X'S) 
RIDE C   (  59,X'S) H   ( 593,X'S) H   ( 591,X'S) H   ( 592,X'S) 
RIDE C   (  60,X'S) H   ( 602,X'S) H   ( 601,X'S) 
RIDE C   (  62,X'S) H   ( 621,X'S) 
RIDE C   (  63,X'S) H   ( 631,X'S) 
RIDE C   (  66,X'S) H   ( 662,X'S) H   ( 661,X'S) H   ( 663,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   (  71,X'S) H   ( 711,X'S) H   ( 712,X'S) 
RIDE C   (  72,X'S) H   ( 721,X'S) H   ( 722,X'S) 
RIDE C   (  73,X'S) H   ( 731,X'S) H   ( 732,X'S) 
RIDE C   (  78,X'S) H   ( 783,X'S) H   ( 782,X'S) H   ( 781,X'S) 
RIDE C   (  80,X'S) H   ( 802,X'S) H   ( 801,X'S) 
RIDE C   (  82,X'S) H   ( 822,X'S) H   ( 821,X'S) 
RIDE C   (  83,X'S) H   ( 831,X'S) 
RIDE C   (  86,X'S) H   ( 863,X'S) H   ( 861,X'S) H   ( 862,X'S) 
RIDE C   (  87,X'S) H   ( 872,X'S) H   ( 871,X'S) H   ( 873,X'S) 
END                                                                             
;
_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, 0.010000 = C(70) TO C(71) 
U(IJ)'S  0.0, 0.010000 = C(72) TO C(73) 
DISTANCE 1.550000 , 0.050000 = C(70) TO C(73) 
U(IJ)'S  0.0, 0.010000 = C(2) TO C(3) 
END                                                                             
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