Highly enantioselective addition of sulfur-containing heterocycles to isatin-derived ketimines.
Franc, Michael; Urban, Michal; Císařová, Ivana; Veselý, Jan; Organic & biomolecular chemistry 17 (2019) 7309–7314; doi:10.1039/c9ob01338e

data_7156993
_publ_section_title
;
 Highly enantioselective addition of sulfur-containing heterocycles to
 isatin-derived ketimines.
;
_journal_issue                   31
_journal_name_full               'Organic &amp; biomolecular chemistry'
_journal_page_first              7309
_journal_page_last               7314
_journal_paper_doi               10.1039/c9ob01338e
_journal_volume                  17
_journal_year                    2019
_chemical_absolute_configuration ad
_chemical_compound_source        'synthesized by the authors'
_chemical_formula_moiety         'C35 H31 Br N2 O4 S'
_chemical_formula_sum            'C35 H31 Br N2 O4 S'
_chemical_formula_weight         655.59
_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'
_symmetry_space_group_name_Hall  'P 2ac 2ab'
_symmetry_space_group_name_H-M   'P 21 21 21'
_atom_sites_solution_hydrogens   mixed
_audit_creation_method           SHELXL-2018/1
_audit_update_record
;
2018-07-01 deposited with the CCDC.    2019-07-10 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   7.2208(4)
_cell_length_b                   16.3286(9)
_cell_length_c                   27.1076(12)
_cell_measurement_reflns_used    7766
_cell_measurement_temperature    150(2)
_cell_measurement_theta_max      25.8598
_cell_measurement_theta_min      2.4947
_cell_volume                     3196.1(3)
_computing_cell_refinement       'SAINT V8.38A (Bruker AXS Inc., 2017)'
_computing_data_collection       'Bruker Instrument Service vV6.2.6'
_computing_data_reduction        'SAINT V8.38A (Bruker AXS Inc., 2017)'
_computing_structure_refinement  'SHELXL-2018/1 (Sheldrick, 2018)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_diffrn_ambient_temperature      150(2)
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measurement_device_type  'Bruker D8 VENTURE Kappa Duo PHOTON 100 CMOS'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_monochromator  'Quazar Mo multilayer optic'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0638
_diffrn_reflns_av_unetI/netI     0.0510
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       20
_diffrn_reflns_limit_k_min       -19
_diffrn_reflns_limit_l_max       33
_diffrn_reflns_limit_l_min       -33
_diffrn_reflns_number            32635
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.018
_diffrn_reflns_theta_min         2.495
_diffrn_source                   'I\mS  micro-focus sealed tube'
_exptl_absorpt_coefficient_mu    1.392
_exptl_absorpt_correction_T_max  0.91
_exptl_absorpt_correction_T_min  0.74
_exptl_absorpt_correction_type   'Numerical Mu From Formula'
_exptl_absorpt_process_details
;
SADABS-2016/2 - Bruker AXS area detector scaling and absorption correction
;
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.362
_exptl_crystal_description       prism
_exptl_crystal_F_000             1352
_exptl_crystal_size_max          0.305
_exptl_crystal_size_mid          0.087
_exptl_crystal_size_min          0.073
_refine_diff_density_max         0.290
_refine_diff_density_min         -0.404
_refine_diff_density_rms         0.055
_refine_ls_abs_structure_details
;
 Flack x determined using 1839 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.002(4)
_refine_ls_extinction_coef       0.0036(4)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2018/1 (Sheldrick 2018)'
_refine_ls_goodness_of_fit_ref   1.036
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     392
_refine_ls_number_reflns         6251
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.036
_refine_ls_R_factor_all          0.0578
_refine_ls_R_factor_gt           0.0355
_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^)+(0.0265P)^2^+1.1717P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0661
_refine_ls_wR_factor_ref         0.0717
_reflns_Friedel_coverage         0.757
_reflns_Friedel_fraction_full    1.000
_reflns_Friedel_fraction_max     0.998
_reflns_number_gt                5023
_reflns_number_total             6251
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c9ob01338e2.cif
_cod_data_source_block           mo_fm309_vesely
_cod_depositor_comments          'Adding full bibliography for 7156993.cif.'
_cod_database_code               7156993
_shelx_shelxl_version_number     2018/1
_shelx_estimated_absorpt_t_min   0.676
_shelx_estimated_absorpt_t_max   0.905
_shelx_res_checksum              88676