Enantioselective construction of triaryl-substituted all-carbon quaternary stereocenters via organocatalytic arylation of oxindoles with azonaphthalenes
Chen, Pengquan; Lv, Mei-Jun; Cheng, Jun Kee; Xiang, Shao-Hua; Ren, Xiang-Zhong; Zhang, Junmin; Tan, Bin; Chemical Science 14 (2023) 2330–2335; doi:10.1039/D2SC07103G

data_1568421
_publ_section_title
;
 Enantioselective construction of triaryl-substituted all-carbon
 quaternary stereocenters via organocatalytic arylation of oxindoles with
 azonaphthalenes
;
_journal_issue                   9
_journal_name_full               'Chemical Science'
_journal_page_first              2330
_journal_page_last               2335
_journal_paper_doi               10.1039/D2SC07103G
_journal_volume                  14
_journal_year                    2023
_chemical_absolute_configuration ad
_chemical_formula_moiety         'C31 H26 Cl3 N3 O5'
_chemical_formula_sum            'C31 H26 Cl3 N3 O5'
_chemical_formula_weight         626.90
_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   mixed
_atom_sites_solution_primary     iterative
_audit_creation_date             2022-11-09
_audit_creation_method
;
Olex2 1.3
(compiled 2020.11.12 svn.r5f609507 for OlexSys, GUI svn.r6408)
;
_audit_update_record
;
2022-12-13 deposited with the CCDC.	2023-02-06 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   9.9368(2)
_cell_length_b                   17.0962(3)
_cell_length_c                   17.1478(3)
_cell_measurement_reflns_used    9423
_cell_measurement_temperature    100.0(2)
_cell_measurement_theta_max      68.21
_cell_measurement_theta_min      3.65
_cell_volume                     2913.09(9)
_computing_cell_refinement       'SAINT V8.40A (Bruker, 2019)'
_computing_data_collection       'Apex3 (Bruker 2018)'
_computing_data_reduction        'SAINT V8.40A (Bruker, 2019)'
_computing_molecular_graphics    'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL  (Sheldrick, 2008)'
_computing_structure_solution    'olex2.solve 1.3 (Bourhis et al., 2015)'
_diffrn_ambient_temperature      100.0(2)
_diffrn_detector                 'Bruker PHOTON 100 area detector'
_diffrn_detector_area_resol_mean 7.9
_diffrn_detector_type            'CMOS area detector'
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_device       'three-circle diffractometer'
_diffrn_measurement_device_type  'Bruker D8 venture microsource'
_diffrn_measurement_method       '\w and \f scans'
_diffrn_radiation_monochromator  'mirror optics'
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0324
_diffrn_reflns_av_unetI/netI     0.0206
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       20
_diffrn_reflns_limit_k_min       -20
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            45400
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_theta_full        67.679
_diffrn_reflns_theta_max         68.207
_diffrn_reflns_theta_min         3.651
_diffrn_source                   'microfocus sealed X-ray tube'
_diffrn_source_current           1.11
_diffrn_source_power             0.0555
_diffrn_source_type              'Incoatec I\ms'
_diffrn_source_voltage           50.0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    3.235
_exptl_absorpt_correction_T_max  0.7531
_exptl_absorpt_correction_T_min  0.5671
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   SADABS
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.429
_exptl_crystal_description       block
_exptl_crystal_F_000             1296
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.1
_refine_diff_density_max         0.181
_refine_diff_density_min         -0.175
_refine_diff_density_rms         0.031
_refine_ls_abs_structure_details
;
 Flack x determined using 2262 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.019(2)
_refine_ls_extinction_coef       0.00229(11)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2018/3 (Sheldrick 2018)'
_refine_ls_goodness_of_fit_ref   1.056
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     388
_refine_ls_number_reflns         5328
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.056
_refine_ls_R_factor_all          0.0187
_refine_ls_R_factor_gt           0.0184
_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^)+(0.0185P)^2^+0.7504P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0464
_refine_ls_wR_factor_ref         0.0465
_reflns_Friedel_coverage         0.769
_reflns_Friedel_fraction_full    0.999
_reflns_Friedel_fraction_max     0.998
_reflns_number_gt                5277
_reflns_number_total             5328
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d2sc07103g2.cif
_cod_data_source_block           111
_cod_depositor_comments          'Adding full bibliography for 1568421.cif.'
_cod_database_code               1568421
_shelx_shelxl_version_number     2018/3
_shelx_estimated_absorpt_t_max   0.738
_shelx_estimated_absorpt_t_min   0.564
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All N(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Aromatic/amide H refined with riding coordinates:
 N3(H3), C12(H12), C14(H14), C15(H15), C17(H17), C19(H19), C21(H21), C23(H23),
 C24(H24), C26(H26), C27(H27), C28(H28), C29(H29)
2.b Idealised Me refined as rotating group:
 C1(H1A,H1B,H1C), C9(H9A,H9B,H9C), C10(H10A,H10B,H10C), C11(H11A,H11B,H11C)
;
_shelx_res_checksum              66706
_shelx_hkl_checksum              5279
_olex2_submission_special_instructions 'No special instructions were received'