Conversion of Two Stereocenters to One or Two Chiral Axes: Atroposelective Synthesis of 2,3-Diarylbenzoindoles
Hu, Yu-Long; Wang, Zhe; Yang, Hui; Chen, Jie; Wu, Zi-Bo; Lei, Yibo; Zhou, Ling; Chemical Science  (2019) –; doi:10.1039/C9SC00810A

data_1551075
_publ_section_title
;
 Conversion of Two Stereocenters to One or Two Chiral Axes:
 Atroposelective Synthesis of 2,3-Diarylbenzoindoles
;
_journal_name_full               'Chemical Science'
_journal_paper_doi               10.1039/C9SC00810A
_journal_year                    2019
_chemical_formula_sum            'C35 H25 Br N2 O2'
_chemical_formula_weight         585.47
_space_group_IT_number           4
_symmetry_cell_setting           triclinic
_symmetry_space_group_name_Hall  'P 2yb'
_symmetry_space_group_name_H-M   'P 1 21 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_audit_update_record
;
2019-03-27 deposited with the CCDC.    2019-05-20 downloaded from the CCDC.
;
_cell_angle_alpha                90.00
_cell_angle_beta                 104.922(3)
_cell_angle_gamma                90.00
_cell_formula_units_Z            2
_cell_length_a                   8.5449(16)
_cell_length_b                   11.993(2)
_cell_length_c                   13.598(2)
_cell_measurement_reflns_used    2358
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      22.923
_cell_measurement_theta_min      2.305
_cell_volume                     1346.5(4)
_computing_cell_refinement       'Bruker SAINT'
_computing_data_collection       'Bruker APEX2'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      296(2)
_diffrn_measured_fraction_theta_full 0.995
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0238
_diffrn_reflns_av_sigmaI/netI    0.0771
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            7098
_diffrn_reflns_theta_full        25.99
_diffrn_reflns_theta_max         25.99
_diffrn_reflns_theta_min         1.55
_exptl_absorpt_coefficient_mu    1.562
_exptl_absorpt_correction_T_max  0.8918
_exptl_absorpt_correction_T_min  0.8407
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   sadaba
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.444
_exptl_crystal_density_meas      1.444
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             600
_exptl_crystal_size_max          0.23
_exptl_crystal_size_mid          0.18
_exptl_crystal_size_min          0.15
_refine_diff_density_max         0.301
_refine_diff_density_min         -0.283
_refine_diff_density_rms         0.045
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.005(8)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.963
_refine_ls_hydrogen_treatment    constra
_refine_ls_matrix_type           full
_refine_ls_number_parameters     362
_refine_ls_number_reflns         4936
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      0.963
_refine_ls_R_factor_all          0.0535
_refine_ls_R_factor_gt           0.0368
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0000P)^2^+0.0068P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0799
_refine_ls_wR_factor_ref         0.0859
_reflns_number_gt                3785
_reflns_number_total             5307
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            c9sc00810a2.cif
_cod_data_source_block           xb1847_0m
_cod_original_cell_volume        1346.4(4)
_cod_original_sg_symbol_H-M      P21
_cod_original_formula_sum        'C35 H25 Br1 N2 O2'
_cod_database_code               1551075