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_4135232
_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_formula_moiety         'C45 H33 Cl N4 O3, C H2 Cl2'
_chemical_formula_sum            'C46 H35 Cl3 N4 O3'
_chemical_formula_weight         798.13
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2019-07-04
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_cell_angle_alpha                110.790(2)
_cell_angle_beta                 94.411(2)
_cell_angle_gamma                96.326(2)
_cell_formula_units_Z            2
_cell_length_a                   11.7169(15)
_cell_length_b                   13.0843(17)
_cell_length_c                   13.9715(18)
_cell_measurement_reflns_used    3756
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      26.71
_cell_measurement_theta_min      2.50
_cell_volume                     1974.7(4)
_computing_cell_refinement       'SAINT v7.68A (Bruker, 2009)'
_computing_data_reduction        'SAINT v7.68A (Bruker, 2009)'
_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      296.15
_diffrn_measured_fraction_theta_full 0.983
_diffrn_measured_fraction_theta_max 0.975
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0144
_diffrn_reflns_av_unetI/netI     0.0319
_diffrn_reflns_Laue_measured_fraction_full 0.983
_diffrn_reflns_Laue_measured_fraction_max 0.975
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            11079
_diffrn_reflns_point_group_measured_fraction_full 0.983
_diffrn_reflns_point_group_measured_fraction_max 0.975
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.372
_diffrn_reflns_theta_min         2.504
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.280
_exptl_absorpt_correction_T_max  0.7455
_exptl_absorpt_correction_T_min  0.6754
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
'SADABS-2008/1 (Bruker,2008) was used for absorption correction. wR2(int) was 0.0521 before and 0.0277 after correction. The Ratio of minimum to maximum transmission is 0.9060. The \l/2 correction factor is 0.0015.'
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.342
_exptl_crystal_description       block
_exptl_crystal_F_000             828
_refine_diff_density_max         0.994
_refine_diff_density_min         -0.602
_refine_diff_density_rms         0.050
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.045
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     505
_refine_ls_number_reflns         7872
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.045
_refine_ls_R_factor_all          0.0901
_refine_ls_R_factor_gt           0.0637
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0982P)^2^+1.0273P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1785
_refine_ls_wR_factor_ref         0.2009
_reflns_Friedel_coverage         0.000
_reflns_number_gt                5511
_reflns_number_total             7872
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            ja0c00208_si_003.cif
_cod_data_source_block           sf20190702b_0m
_cod_database_code               4135232
_shelx_shelxl_version_number     2016/6
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All N(H) groups
2.a Ternary CH refined with riding coordinates:
 C1(H1)
2.b Secondary CH2 refined with riding coordinates:
 C26(H26A,H26B), C46(H46A,H46B)
2.c Aromatic/amide H refined with riding coordinates:
 N2(H2), N3(H3), N4(H4), C4(H4A), C5(H5), C6(H6), C7(H7), C13(H13), C14(H14),
 C15(H15), C16(H16), C18(H18), C21(H21), C22(H22), C23(H23), C24(H24), C28(H28),
  C29(H29), C30(H30), C31(H31), C32(H32), C34(H34), C35(H35), C37(H37),
 C38(H38), C41(H41), C42(H42), C43(H43), C44(H44), C45(H45)
;
_shelx_res_checksum              57109
_shelx_hkl_checksum              5521
_olex2_submission_special_instructions 'No special instructions were received'