Catalytic Asymmetric Conjugate Addition and Sulfenylation of Diarylthiazolidin-2,4-diones.
Jiao, Lihui; Bu, Liwei; Ye, Xinyi; Zhao, Xiaowei; Jiang, Zhiyong; The Journal of organic chemistry 81 (2016) 9620–9629; doi:10.1021/acs.joc.6b01637

data_4037166
_publ_section_title
;
 Catalytic Asymmetric Conjugate Addition and Sulfenylation of
 Diarylthiazolidin-2,4-diones.
;
_journal_issue                   20
_journal_name_full               'The Journal of organic chemistry'
_journal_page_first              9620
_journal_page_last               9629
_journal_paper_doi               10.1021/acs.joc.6b01637
_journal_volume                  81
_journal_year                    2016
_chemical_absolute_configuration ad
_chemical_formula_moiety         'C23 H19 N O5 S2'
_chemical_formula_sum            'C23 H19 N O5 S2'
_chemical_formula_weight         453.51
_space_group_crystal_system      orthorhombic
_space_group_IT_number           19
_space_group_name_Hall           'P 2ac 2ab'
_space_group_name_H-M_alt        'P 21 21 21'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_audit_creation_date             2016-06-28
_audit_creation_method
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Olex2 1.2
(compiled 2016.02.19 svn.r3266 for OlexSys, GUI svn.r5155)
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_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   8.62184(14)
_cell_length_b                   15.2120(3)
_cell_length_c                   16.4772(2)
_cell_measurement_reflns_used    4044
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      70.5990
_cell_measurement_theta_min      3.9350
_cell_volume                     2161.07(6)
_computing_cell_refinement
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_computing_data_collection
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CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_computing_data_reduction
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXS (Sheldrick, 2008)'
_diffrn_ambient_temperature      293(2)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 16.2312
_diffrn_detector_type            Eos
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.987
_diffrn_measurement_details
;
  1 omega  -52.00   24.00   1.0000    2.5000
omega____ theta____ kappa____ phi______ frames
    -      -33.5000   57.0000  -90.0000 76

  2 omega    0.00   35.00   1.0000    2.5000
omega____ theta____ kappa____ phi______ frames
    -      -33.5000   57.0000   30.0000 35

  3 omega   12.00  104.00   1.0000    2.5000
omega____ theta____ kappa____ phi______ frames
    -       36.4734   77.0000   60.0000 92

  4 omega   57.00  105.00   1.0000    2.5000
omega____ theta____ kappa____ phi______ frames
    -       36.4734  178.0000   30.0000 48

  5 omega   44.00   73.00   1.0000    2.5000
omega____ theta____ kappa____ phi______ frames
    -       36.4734  -99.0000  -30.0000 29

  6 omega   65.00   92.00   1.0000    2.5000
omega____ theta____ kappa____ phi______ frames
    -       36.4734   57.0000  150.0000 27

  7 omega   27.00   60.00   1.0000    2.5000
omega____ theta____ kappa____ phi______ frames
    -       36.4734   57.0000  150.0000 33

  8 omega   58.00   86.00   1.0000    2.5000
omega____ theta____ kappa____ phi______ frames
    -       36.4734  178.0000   60.0000 28

  9 omega   38.00   91.00   1.0000   12.5000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -30.0000 -180.0000 53

 10 omega   41.00   91.00   1.0000   12.5000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -30.0000  -30.0000 50

 11 omega   37.00   88.00   1.0000   12.5000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -30.0000 -120.0000 51

 12 omega   46.00   87.00   1.0000   12.5000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -45.0000   30.0000 41

 13 omega   89.00  177.00   1.0000   12.5000
omega____ theta____ kappa____ phi______ frames
    -      108.0000   45.0000  -60.0000 88

 14 omega   47.00  108.00   1.0000   12.5000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -94.0000   60.0000 61

 15 omega   40.00   66.00   1.0000   12.5000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -30.0000 -150.0000 26

 16 omega   63.00  177.00   1.0000   12.5000
omega____ theta____ kappa____ phi______ frames
    -      108.0000   15.0000 -180.0000 114
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Xcalibur, Eos, Gemini'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_UB_11      -0.0423565000
_diffrn_orient_matrix_UB_12      -0.0893031000
_diffrn_orient_matrix_UB_13      0.0381393000
_diffrn_orient_matrix_UB_21      0.0929926000
_diffrn_orient_matrix_UB_22      -0.0475692000
_diffrn_orient_matrix_UB_23      -0.0667407000
_diffrn_orient_matrix_UB_31      0.1465664000
_diffrn_orient_matrix_UB_32      0.0043559000
_diffrn_orient_matrix_UB_33      0.0532270000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0294
_diffrn_reflns_av_unetI/netI     0.0385
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.987
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            8178
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.979
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         70.915
_diffrn_reflns_theta_min         3.955
_diffrn_source                   'Enhance (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    2.538
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.74719
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.394
_exptl_crystal_description       prism
_exptl_crystal_F_000             944
_exptl_crystal_size_max          0.15
_exptl_crystal_size_mid          0.1
_exptl_crystal_size_min          0.08
_refine_diff_density_max         0.189
_refine_diff_density_min         -0.227
_refine_diff_density_rms         0.043
_refine_ls_abs_structure_details
;
 Flack x determined using 1527 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.015(10)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.033
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     281
_refine_ls_number_reflns         4097
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.033
_refine_ls_R_factor_all          0.0381
_refine_ls_R_factor_gt           0.0348
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0551P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0886
_refine_ls_wR_factor_ref         0.0913
_reflns_Friedel_coverage         0.737
_reflns_Friedel_fraction_full    0.998
_reflns_Friedel_fraction_max     0.969
_reflns_number_gt                3827
_reflns_number_total             4097
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            jo6b01637_si_002.cif
_cod_data_source_block           blwyanghua
_cod_original_cell_volume        2161.08(6)
_cod_database_code               4037166
_chemical_oxdiff_formula         C1H1O1N1S2
_reflns_odcompleteness_completeness 99.91
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Secondary CH2 refined with riding coordinates:
 C10(H10A,H10B)
2.b Aromatic/amide H refined with riding coordinates:
 C5(H5), C6(H6), C7(H7), C8(H8), C9(H9), C12(H12), C13(H13), C14(H14),
 C15(H15), C16(H16), C18(H18), C19(H19), C21(H21), C22(H22)
2.c Idealised Me refined as rotating group:
 C23(H23A,H23B,H23C)
;
_shelx_res_checksum              38692
_shelx_hkl_checksum              11421
_shelx_shelxl_version_number     2014/7
_olex2_submission_special_instructions 'No special instructions were received'