Enantioselective sulfonylation to construct 3-sulfonylated oxindoles.
Li, Hongye; Zhou, Yuqiao; Tan, Zheng; Wang, Xiangyu; Zhang, Yuxin; Wang, Fei; Feng, Xiaoming; Liu, Xiaohua; Chemical communications (Cambridge, England) 60 (2024) 4354–4357; doi:10.1039/d4cc00802b

data_7132885
_publ_section_title
;
 Enantioselective sulfonylation to construct 3-sulfonylated oxindoles.
;
_journal_issue                   32
_journal_name_full               'Chemical communications (Cambridge, England)'
_journal_page_first              4354
_journal_page_last               4357
_journal_paper_doi               10.1039/d4cc00802b
_journal_volume                  60
_journal_year                    2024
_chemical_absolute_configuration ad
_chemical_formula_moiety         'C21 H23 N O3 S'
_chemical_formula_sum            'C21 H23 N O3 S'
_chemical_formula_weight         369.46
_space_group_crystal_system      monoclinic
_space_group_IT_number           4
_space_group_name_Hall           'P 2yb'
_space_group_name_H-M_alt        'P 1 21 1'
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-2019/1
_audit_update_record
;
2023-07-26 deposited with the CCDC.	2024-03-22 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 113.0000(10)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   10.5669(3)
_cell_length_b                   8.0829(2)
_cell_length_c                   11.7127(3)
_cell_measurement_reflns_used    9871
_cell_measurement_temperature    173(2)
_cell_measurement_theta_max      68.26
_cell_measurement_theta_min      4.10
_cell_volume                     920.87(4)
_computing_cell_refinement       'Bruker SAINT'
_computing_data_collection       'Bruker APEX3'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-2019/1 (Sheldrick, 2019)'
_computing_structure_solution    'SHELXT (Sheldrick 2008)'
_diffrn_ambient_temperature      173(2)
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device_type  'Bruker D8 Venture Photon II'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0378
_diffrn_reflns_av_unetI/netI     0.0331
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            14671
_diffrn_reflns_point_group_measured_fraction_full 0.972
_diffrn_reflns_point_group_measured_fraction_max 0.972
_diffrn_reflns_theta_full        67.679
_diffrn_reflns_theta_max         68.254
_diffrn_reflns_theta_min         4.100
_exptl_absorpt_coefficient_mu    1.728
_exptl_absorpt_correction_T_max  0.9619
_exptl_absorpt_correction_T_min  0.7054
_exptl_absorpt_correction_type   numerical
_exptl_absorpt_process_details   'SADABS (Krause et al., 2015)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.332
_exptl_crystal_description       block
_exptl_crystal_F_000             392
_exptl_crystal_recrystallization_method
'Re-crystallisation from solvent: CDCl3, PE'
_exptl_crystal_size_max          0.357
_exptl_crystal_size_mid          0.133
_exptl_crystal_size_min          0.072
_refine_diff_density_max         0.427
_refine_diff_density_min         -0.233
_refine_diff_density_rms         0.035
_refine_ls_abs_structure_details
; 
 Flack x determined using 1406 quotients [(I+)-(I-)]/[(I+)+(I-)] 
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259). 
;
_refine_ls_abs_structure_Flack   0.048(6)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.065
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     239
_refine_ls_number_reflns         3277
_refine_ls_number_restraints     2
_refine_ls_restrained_S_all      1.065
_refine_ls_R_factor_all          0.0261
_refine_ls_R_factor_gt           0.0257
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0298P)^2^+0.1718P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0633
_refine_ls_wR_factor_ref         0.0636
_reflns_Friedel_coverage         0.809
_reflns_Friedel_fraction_full    0.942
_reflns_Friedel_fraction_max     0.942
_reflns_number_gt                3233
_reflns_number_total             3277
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d4cc00802b2.cif
_cod_data_source_block           lzj037
_cod_depositor_comments          'Adding full bibliography for 7132885.cif.'
_cod_original_sg_symbol_H-M      'P 21'
_cod_database_code               7132885
_shelx_shelxl_version_number     2019/1
_shelx_estimated_absorpt_t_min   0.577
_shelx_estimated_absorpt_t_max   0.886
_shelx_res_checksum              73565
_shelx_hkl_checksum              30178