Enantioselective access to 3,3'-disubstituted oxindole derivatives by N-heterocyclic carbene catalysis.
Wang, Xiaomei; Zeng, Weixing; Li, Shi-Wu; Pian, Jixin; Zhao, Zhifei; Organic & biomolecular chemistry 23 (2025) 5527–5532; doi:10.1039/d5ob00374a

data_7160504
_publ_section_title
;
 Enantioselective access to 3,3'-disubstituted oxindole derivatives by
 N-heterocyclic carbene catalysis.
;
_journal_issue                   23
_journal_name_full               'Organic &amp; biomolecular chemistry'
_journal_page_first              5527
_journal_page_last               5532
_journal_paper_doi               10.1039/d5ob00374a
_journal_volume                  23
_journal_year                    2025
_chemical_absolute_configuration ad
_chemical_formula_moiety         'C30 H25 N O7'
_chemical_formula_sum            'C30 H25 N O7'
_chemical_formula_weight         511.51
_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   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2024-09-18
_audit_creation_method
;
Olex2 1.3
(compiled 2020.11.12 svn.r5f609507 for OlexSys, GUI svn.r6408)
;
_audit_update_record
;
2024-12-05 deposited with the CCDC.	2025-04-11 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 102.057(2)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   9.0595(3)
_cell_length_b                   9.2127(3)
_cell_length_c                   15.4455(5)
_cell_measurement_reflns_used    9872
_cell_measurement_temperature    173.0
_cell_measurement_theta_max      72.06
_cell_measurement_theta_min      5.23
_cell_volume                     1260.68(7)
_computing_cell_refinement       'SAINT V8.38A (Bruker, 2018)'
_computing_data_reduction        'SAINT V8.38A (Bruker, 2018)'
_computing_molecular_graphics    'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2019/2 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_diffrn_ambient_temperature      173.0
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.993
_diffrn_measurement_device_type  'Bruker D8 Venture'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0426
_diffrn_reflns_av_unetI/netI     0.0354
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.993
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            16713
_diffrn_reflns_point_group_measured_fraction_full 0.993
_diffrn_reflns_point_group_measured_fraction_max 0.984
_diffrn_reflns_theta_full        67.679
_diffrn_reflns_theta_max         72.052
_diffrn_reflns_theta_min         4.992
_diffrn_source_current           1.1
_diffrn_source_power             0.055
_diffrn_source_voltage           50.0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.796
_exptl_absorpt_correction_T_max  0.7536
_exptl_absorpt_correction_T_min  0.6778
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.1202 before and 0.0675 after correction.
The Ratio of minimum to maximum transmission is 0.8994.
The \l/2 correction factor is Not present.
;
_exptl_crystal_density_diffrn    1.347
_exptl_crystal_description       block
_exptl_crystal_F_000             536
_exptl_crystal_size_max          0.14
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.11
_refine_diff_density_max         0.233
_refine_diff_density_min         -0.163
_refine_diff_density_rms         0.032
_refine_ls_abs_structure_details
;
 Flack x determined using 1951 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.03(9)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.044
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     345
_refine_ls_number_reflns         4871
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.044
_refine_ls_R_factor_all          0.0387
_refine_ls_R_factor_gt           0.0344
_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^)+(0.0321P)^2^+0.2582P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0785
_refine_ls_wR_factor_ref         0.0811
_reflns_Friedel_coverage         0.859
_reflns_Friedel_fraction_full    0.988
_reflns_Friedel_fraction_max     0.974
_reflns_number_gt                4528
_reflns_number_total             4871
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d5ob00374a2.cif
_cod_data_source_block           11
_cod_depositor_comments          'Adding full bibliography for 7160504.cif.'
_cod_database_code               7160504
_shelx_shelxl_version_number     2019/2
_shelx_estimated_absorpt_t_max   0.918
_shelx_estimated_absorpt_t_min   0.897
_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:
 C2(H2A,H2B), C15(H15A,H15B), C18(H18A,H18B)
2.b Aromatic/amide H refined with riding coordinates:
 C8(H8), C9(H9), C11(H11), C12(H12), C20(H20), C21(H21), C22(H22), C23(H23),
 C24(H24), C26(H26), C27(H27), C28(H28), C29(H29)
2.c Idealised Me refined as rotating group:
 C1(H1A,H1B,H1C), C13(H13A,H13B,H13C)
;
_shelx_res_checksum              16481
_olex2_submission_special_instructions 'No special instructions were received'