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_1551074
_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_moiety         'C48 H33 Br N2 O4 S'
_chemical_formula_sum            'C48 H33 Br N2 O4 S'
_chemical_formula_weight         813.73
_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'
_symmetry_space_group_name_Hall  'P 2yb'
_symmetry_space_group_name_H-M   'P 1 21 1'
_atom_sites_solution_hydrogens   mixed
_audit_creation_date             2019-03-26
_audit_creation_method
;
Olex2 1.2-beta
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_audit_update_record
;
2019-03-26 deposited with the CCDC.    2019-05-20 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 93.392(6)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   15.033(5)
_cell_length_b                   8.026(2)
_cell_length_c                   18.952(6)
_cell_measurement_reflns_used    2071
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      18.62
_cell_measurement_theta_min      2.71
_cell_volume                     2282.6(12)
_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)'
_diffrn_ambient_temperature      296.15
_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_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0403
_diffrn_reflns_av_unetI/netI     0.1003
_diffrn_reflns_Laue_measured_fraction_full 0.995
_diffrn_reflns_Laue_measured_fraction_max 0.995
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_h_min       -17
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            11426
_diffrn_reflns_point_group_measured_fraction_full 0.891
_diffrn_reflns_point_group_measured_fraction_max 0.891
_diffrn_reflns_theta_full        24.997
_diffrn_reflns_theta_max         24.997
_diffrn_reflns_theta_min         1.076
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.988
_exptl_absorpt_correction_T_max  0.7454
_exptl_absorpt_correction_T_min  0.6361
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
'SADABS-2008/1 (Bruker,2008) was used for absorption correction. wR2(int) was 0.0854 before and 0.0627 after correction. The Ratio of minimum to maximum transmission is 0.8534. The \l/2 correction factor is 0.0015.'
_exptl_crystal_colour            'clear light colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.184
_exptl_crystal_description       block
_exptl_crystal_F_000             836
_exptl_crystal_size_max          0.21
_exptl_crystal_size_mid          0.11
_exptl_crystal_size_min          0.11
_refine_diff_density_max         0.935
_refine_diff_density_min         -0.379
_refine_diff_density_rms         0.149
_refine_ls_abs_structure_details
;
 Flack x determined using 1334 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.049(11)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.994
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     509
_refine_ls_number_reflns         7175
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      0.994
_refine_ls_R_factor_all          0.1054
_refine_ls_R_factor_gt           0.0640
_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^)+(0.1141P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1739
_refine_ls_wR_factor_ref         0.2060
_reflns_Friedel_coverage         0.661
_reflns_Friedel_fraction_full    0.769
_reflns_Friedel_fraction_max     0.769
_reflns_number_gt                4502
_reflns_number_total             7175
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c9sc00810a2.cif
_cod_data_source_block           xb1989_0m_sq
_cod_original_cell_volume        2282.5(12)
_cod_database_code               1551074
_shelx_shelxl_version_number     2014/7
_shelx_estimated_absorpt_t_max   0.899
_shelx_estimated_absorpt_t_min   0.819
_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:
 C2(H2), C3(H3), C7(H7), C8(H8), C10(H10), C12(H12), C13(H13), C14(H14),
 C15(H15), C16(H16), C19(H19), C20(H20), C21(H21), C22(H22), C27(H27), C28(H28),
  C29(H29), C30(H30), C32(H32), C33(H33), C36(H36), C37(H37), C39(H39),
 C40(H40), C44(H44), C45(H45), C46(H46), C47(H47), C48(H48)
2.b Idealised Me refined as rotating group:
 C41(H41A,H41B,H41C)
;
_shelx_res_checksum              68408
_olex2_submission_special_instructions 'No special instructions were received'
_platon_squeeze_void_probe_radius 1.20