Atroposelective Access to Oxindole-Based Axially Chiral Styrenes via the Strategy of Catalytic Kinetic Resolution.
Ma, Chun; Sheng, Feng-Tao; Wang, Hai-Qing; Deng, Shuang; Zhang, Yu-Chen; Jiao, Yinchun; Tan, Wei; Shi, Feng; Journal of the American Chemical Society  (2020) –; doi:10.1021/jacs.0c00208

data_4135233
_publ_section_title
;
 Atroposelective Access to Oxindole-Based Axially Chiral Styrenes via the
 Strategy of Catalytic Kinetic Resolution.
;
_journal_name_full               'Journal of the American Chemical Society'
_journal_paper_doi               10.1021/jacs.0c00208
_journal_year                    2020
_chemical_absolute_configuration rmad
_chemical_formula_moiety         'C30 H23 N3 O'
_chemical_formula_sum            'C30 H23 N3 O'
_chemical_formula_weight         441.51
_space_group_crystal_system      triclinic
_space_group_IT_number           1
_space_group_name_Hall           'P 1'
_space_group_name_H-M_alt        'P 1'
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     dual
_audit_creation_date             2019-01-08
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_cell_angle_alpha                86.4020(10)
_cell_angle_beta                 87.4260(10)
_cell_angle_gamma                65.9370(10)
_cell_formula_units_Z            4
_cell_length_a                   11.9932(3)
_cell_length_b                   12.6212(3)
_cell_length_c                   17.8528(4)
_cell_measurement_reflns_used    9926
_cell_measurement_temperature    170(2)
_cell_measurement_theta_max      54.98
_cell_measurement_theta_min      3.739
_cell_volume                     2462.09(10)
_computing_cell_refinement       'SAINT v8.37A (Bruker, 2015)'
_computing_data_reduction        'SAINT v8.37A (Bruker, 2015)'
_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    'ShelXT (Sheldrick, 2015)'
_diffrn_ambient_temperature      170.0
_diffrn_measured_fraction_theta_full 0.990
_diffrn_measured_fraction_theta_max 0.987
_diffrn_measurement_device_type  'Bruker D8 Venture'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_type           GaK\a
_diffrn_radiation_wavelength     1.34139
_diffrn_reflns_av_R_equivalents  0.0462
_diffrn_reflns_av_unetI/netI     0.0409
_diffrn_reflns_Laue_measured_fraction_full 0.990
_diffrn_reflns_Laue_measured_fraction_max 0.987
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_number            68127
_diffrn_reflns_point_group_measured_fraction_full 0.978
_diffrn_reflns_point_group_measured_fraction_max 0.972
_diffrn_reflns_theta_full        53.594
_diffrn_reflns_theta_max         54.970
_diffrn_reflns_theta_min         3.512
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.369
_exptl_absorpt_correction_T_max  0.7508
_exptl_absorpt_correction_T_min  0.6008
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
'SADABS-2016/2 (Bruker,2016/2) was used for absorption correction. wR2(int) was 0.1291 before and 0.0757 after correction. The Ratio of minimum to maximum transmission is 0.8002. The \l/2 correction factor is Not present.'
_exptl_crystal_colour            orange
_exptl_crystal_density_diffrn    1.191
_exptl_crystal_description       block
_exptl_crystal_F_000             928
_exptl_crystal_size_max          0.12
_exptl_crystal_size_mid          0.1
_exptl_crystal_size_min          0.05
_refine_diff_density_max         0.235
_refine_diff_density_min         -0.300
_refine_diff_density_rms         0.033
_refine_ls_abs_structure_details
;
 Flack x determined using 8038 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.01(9)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.042
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     1229
_refine_ls_number_reflns         18287
_refine_ls_number_restraints     3
_refine_ls_restrained_S_all      1.042
_refine_ls_R_factor_all          0.0454
_refine_ls_R_factor_gt           0.0435
_refine_ls_shift/su_max          0.003
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0704P)^2^+0.4216P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1186
_refine_ls_wR_factor_ref         0.1207
_reflns_Friedel_coverage         0.970
_reflns_Friedel_fraction_full    0.966
_reflns_Friedel_fraction_max     0.958
_reflns_number_gt                17393
_reflns_number_total             18287
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            ja0c00208_si_002.cif
_cod_data_source_block           20190108sf_0m
_cod_original_cell_volume        2462.10(10)
_cod_database_code               4135233
_shelx_shelxl_version_number     2016/6
_shelx_estimated_absorpt_t_max   0.982
_shelx_estimated_absorpt_t_min   0.957
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All N(H) groups, All N(H,H) groups
2.a Rotating group:
 N3(H3A,H3B), N3A(H3AA,H3AB), N3B(H3BA,H3BB), N3C(H3CA,H3CB)
2.b Secondary CH2 refined with riding coordinates:
 C9(H9A,H9B), C9A(H9AA,H9AB), C9B(H9BA,H9BB), C9C(H9CA,H9CB)
2.c Aromatic/amide H refined with riding coordinates:
 N2(H2), C4(H4), C5(H5), C6(H6), C7(H7), C11(H11), C12(H12), C13(H13),
 C14(H14), C15(H15), C18(H18), C20(H20), C21(H21), C22(H22), C23(H23), C27(H27),
  C28(H28), C29(H29), C30(H30), N2A(H2A), C4A(H4A), C5A(H5A), C6A(H6A),
 C7A(H7A), C11A(H11A), C12A(H12A), C13A(H13A), C14A(H14A), C15A(H15A),
 C18A(H18A), C20A(H20A), C21A(H21A), C22A(H22A), C23A(H23A), C27A(H27A),
 C28A(H28A), C29A(H29A), C30A(H30A), N2B(H2B), C4B(H4B), C5B(H5B), C6B(H6B),
 C7B(H7B), C11B(H11B), C12B(H12B), C13B(H13B), C14B(H14B), C15B(H15B),
 C18B(H18B), C20B(H20B), C21B(H21B), C22B(H22B), C23B(H23B), C27B(H27B),
 C28B(H28B), C29B(H29B), C30B(H30B), N2C(H2C), C4C(H4C), C5C(H5C), C6C(H6C),
 C7C(H7C), C11C(H11C), C12C(H12C), C13C(H13C), C14C(H14C), C15C(H15C),
 C18C(H18C), C20C(H20C), C21C(H21C), C22C(H22C), C23C(H23C), C27C(H27C),
 C28C(H28C), C29C(H29C), C30C(H30C)
;
_shelx_res_checksum              9249
_shelx_hkl_checksum              75780
_shelx_fab_checksum              49522
_olex2_submission_special_instructions 'No special instructions were received'