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_4028353
_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         'C36 H42 O9'
_chemical_formula_sum            'C36 H42 O9'
_chemical_formula_weight         618.70
_space_group_IT_number           2
_symmetry_cell_setting           triclinic
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   difmap
_atom_sites_solution_primary     direct
_cell_angle_alpha                78.786(3)
_cell_angle_beta                 82.948(3)
_cell_angle_gamma                63.226(4)
_cell_formula_units_Z            4
_cell_length_a                   11.3285(5)
_cell_length_b                   12.4990(5)
_cell_length_c                   25.8161(8)
_cell_measurement_reflns_used    28269
_cell_measurement_temperature    120
_cell_measurement_theta_max      66.6979
_cell_measurement_theta_min      3.4908
_cell_volume                     3198.6(2)
_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      120
_diffrn_detector_area_resol_mean 10.4678
_diffrn_measured_fraction_theta_full 0.996
_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  0.042
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       30
_diffrn_reflns_limit_l_min       -30
_diffrn_reflns_number            69247
_diffrn_reflns_theta_full        66.791
_diffrn_reflns_theta_max         66.791
_diffrn_reflns_theta_min         3.494
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.750
_exptl_absorpt_correction_T_max  0.877
_exptl_absorpt_correction_T_min  0.757
_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    1.285
_exptl_crystal_description       plate
_exptl_crystal_F_000             1320
_exptl_crystal_size_max          0.503
_exptl_crystal_size_mid          0.331
_exptl_crystal_size_min          0.202
_refine_diff_density_max         0.49
_refine_diff_density_min         -0.32
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.9222
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     865
_refine_ls_number_reflns         11295
_refine_ls_number_restraints     39
_refine_ls_R_factor_all          0.0440
_refine_ls_R_factor_gt           0.0396
_refine_ls_shift/su_max          0.0013129
_refine_ls_shift/su_mean         0.0000528
_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: 
 760. 0.117E+04 582. 142. 
;
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_all         0.0754
_refine_ls_wR_factor_gt          0.0716
_refine_ls_wR_factor_ref         0.0754
_reflns_limit_h_max              13
_reflns_limit_h_min              -13
_reflns_limit_k_max              14
_reflns_limit_k_min              -14
_reflns_limit_l_max              30
_reflns_limit_l_min              0
_reflns_number_gt                10100
_reflns_number_total             11295
_reflns_threshold_expression     I>2.0\s(I)
_oxford_diffrn_Wilson_B_factor   2.33
_oxford_diffrn_Wilson_scale      0.07
_oxford_refine_ls_r_factor_ref   0.0440
_oxford_refine_ls_scale          3.738(16)
_oxford_reflns_number_all        11295
_oxford_reflns_threshold_expression_ref I>-10.0\s(I)
_cod_data_source_file            jo4007738_si_001_2.cif
_cod_data_source_block           1
_cod_original_sg_symbol_H-M      'P -1 '
_cod_database_code               4028353
_iucr_refine_instruction_details_constraints
;
BLOCK SCALE X'S, U'S 
RIDE C   (   5,X'S) H   (  51,X'S) H   (  52,X'S) H   (  53,X'S) 
RIDE C   (   8,X'S) H   (  81,X'S) H   (  82,X'S) 
RIDE C   (  12,X'S) H   ( 123,X'S) H   ( 122,X'S) H   ( 121,X'S) 
RIDE C   (  15,X'S) H   ( 151,X'S) H   ( 152,X'S) 
RIDE C   (  16,X'S) H   ( 162,X'S)  H   ( 161,X'S) 
RIDE C   (  17,X'S) H   ( 171,X'S) H   ( 172,X'S) 
RIDE C   (  18,X'S) H   ( 182,X'S) H   ( 181,X'S) 
RIDE C   (  21,X'S) H   ( 211,X'S) H   ( 212,X'S) H   ( 213,X'S) 
RIDE C   (  22,X'S) H   ( 221,X'S) 
RIDE C   (  24,X'S) H   ( 242,X'S) H   ( 241,X'S) 
RIDE C   (  28,X'S) H   ( 283,X'S) H   ( 281,X'S) H   ( 282,X'S) 
RIDE C   (  31,X'S) H   ( 311,X'S) H   ( 312,X'S) 
RIDE C   (  32,X'S) H   ( 321,X'S) 
RIDE C   (  33,X'S) H   ( 331,X'S) H   ( 332,X'S) 
RIDE C   (  36,X'S) H   ( 361,X'S) H   ( 362,X'S) H   ( 363,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   (  40,X'S) H   ( 401,X'S) 
RIDE C   (  43,X'S) H   ( 431,X'S) H   ( 433,X'S) H   ( 432,X'S) 
RIDE C   (  44,X'S) H   ( 442,X'S) H   ( 441,X'S) 
RIDE C   (  45,X'S) H   ( 451,X'S) 
RIDE C   (  46,X'S) H   ( 462,X'S) H   ( 461,X'S) 
RIDE C   (  51,X'S) H   ( 511,X'S) 
RIDE C   (  55,X'S) H   ( 551,X'S) H   ( 552,X'S) H   ( 553,X'S) H   ( 554,X'S) 
RIDE C   (  56,X'S) H   ( 561,X'S) 
RIDE C   (  57,X'S) H   ( 571,X'S) 
RIDE C   (  58,X'S) H   ( 581,X'S) H   ( 582,X'S) 
RIDE C   (  59,X'S) H   ( 591,X'S) H   ( 592,X'S) 
RIDE C   (  61,X'S) H   ( 612,X'S) H   ( 613,X'S) H   ( 611,X'S) 
RIDE C   (  62,X'S) H   ( 622,X'S) H   ( 621,X'S) 
RIDE C   (  66,X'S) H   ( 661,X'S) H   ( 662,X'S) H   ( 663,X'S) 
RIDE C   (  69,X'S) H   ( 691,X'S) H   ( 692,X'S) 
RIDE C   (  70,X'S) H   ( 701,X'S) 
RIDE C   (  71,X'S) H   ( 711,X'S) H   ( 712,X'S) 
RIDE C   (  74,X'S) H   ( 742,X'S) H   ( 741,X'S) H   ( 743,X'S) 
RIDE C   (  75,X'S) H   ( 751,X'S) 
RIDE C   (  77,X'S) H   ( 772,X'S) H   ( 771,X'S) 
RIDE C   (  81,X'S) H   ( 811,X'S) H   ( 813,X'S) H   ( 812,X'S) 
RIDE C   (  84,X'S) H   ( 841,X'S) H   ( 842,X'S) 
RIDE C   (  85,X'S) H   ( 851,X'S) H   ( 852,X'S) 
RIDE C   (  86,X'S) H   ( 861,X'S) 
RIDE C   (  87,X'S) H   ( 871,X'S) 
RIDE C   (  88,X'S) H   ( 881,X'S) H   ( 882,X'S) 
RIDE C   (  89,X'S) H   ( 891,X'S) H   ( 892,X'S) 
RIDE C   (  92,X'S) H   ( 921,X'S) H   ( 922,X'S) H   ( 923,X'S) 
RIDE C   (  93,X'S) H   ( 931,X'S) 
RIDE C   (  95,X'S) H   ( 952,X'S) H   ( 951,X'S) 
RIDE C   (  96,X'S) H   ( 961,X'S) H   ( 962,X'S) H   ( 963,X'S) 
END                                                                             
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_iucr_refine_instruction_details_restraints
;
NO 
DISTANCE 1.500000 , 0.0050000 = C(55) TO C(57) 
DISTANCE 1.500000 , 0.0050000 = C(55) TO C(56) 
U(IJ)'S  0.0, 0.0010000 = C(55) TO C(57) 
U(IJ)'S  0.0, 0.0010000 = C(55) TO C(56) 
REM   HREST   START (DO NOT REMOVE THIS LINE) 
REM   HREST   END (DO NOT REMOVE THIS LINE) 
U(IJ)'S  0.0, 0.0050000 = C(84) TO C(85) 
U(IJ)'S  0.0, 0.010000 = C(86) TO C(87) 
U(IJ)'S  0.0, 0.0010000 = C(86) TO C(88) 
U(IJ)'S  0.0, 0.0010000 = C(87) TO C(89) 
DISTANCE 1.350000 , 0.0050000 = C(87) TO C(89) 
END                                                                             
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