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_1551073
_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_absolute_configuration rm
_chemical_formula_moiety         'C36 H27 Br N2 O2, C3 H8 O'
_chemical_formula_sum            'C39 H35 Br N2 O3'
_chemical_formula_weight         659.60
_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'
_symmetry_space_group_name_Hall  'P 2ac 2ab'
_symmetry_space_group_name_H-M   'P 21 21 21'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2019-01-19
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_audit_update_record
;
2019-01-19 deposited with the CCDC.    2019-05-20 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   11.153(2)
_cell_length_b                   11.570(2)
_cell_length_c                   25.918(4)
_cell_measurement_reflns_used    2717
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      19.497
_cell_measurement_theta_min      2.359
_cell_volume                     3344.5(10)
_computing_cell_refinement       'SAINT v7.68A (Bruker, 2009)'
_computing_data_collection       '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 1.000
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0528
_diffrn_reflns_av_unetI/netI     0.0949
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       26
_diffrn_reflns_limit_l_min       -32
_diffrn_reflns_number            18279
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.989
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.339
_diffrn_reflns_theta_min         1.571
_exptl_absorpt_coefficient_mu    1.269
_exptl_absorpt_correction_T_max  0.7454
_exptl_absorpt_correction_T_min  0.5134
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
'SADABS-2008/1 (Bruker,2008) was used for absorption correction. wR2(int) was 0.0929 before and 0.0645 after correction. The Ratio of minimum to maximum transmission is 0.6888. The \l/2 correction factor is 0.0015.'
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.310
_exptl_crystal_description       block
_exptl_crystal_F_000             1368
_exptl_crystal_size_max          0.05
_exptl_crystal_size_mid          0.04
_exptl_crystal_size_min          0.03
_refine_diff_density_max         0.719
_refine_diff_density_min         -0.576
_refine_diff_density_rms         0.049
_refine_ls_abs_structure_details
;
 Flack x determined using 1122 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.036(7)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.030
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     411
_refine_ls_number_reflns         6740
_refine_ls_number_restraints     6
_refine_ls_restrained_S_all      1.032
_refine_ls_R_factor_all          0.1314
_refine_ls_R_factor_gt           0.0597
_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^)+(0.0754P)^2^+0.3433P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1475
_refine_ls_wR_factor_ref         0.1773
_reflns_Friedel_coverage         0.764
_reflns_Friedel_fraction_full    0.998
_reflns_Friedel_fraction_max     0.978
_reflns_number_gt                3530
_reflns_number_total             6740
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c9sc00810a2.cif
_cod_data_source_block           xb1852
_cod_original_cell_volume        3344.4(10)
_cod_database_code               1551073
_shelx_shelxl_version_number     2018/3
_shelx_estimated_absorpt_t_max   0.963
_shelx_estimated_absorpt_t_min   0.939
_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, All O(H) groups
2. Uiso/Uaniso restraints and constraints
Uanis(C39) \\sim Ueq: with sigma of 0.01 and sigma for terminal atoms of 0.02
3.a Ternary CH refined with riding coordinates:
 C1(H1), C2(H2B), C37(H37)
3.b Aromatic/amide H refined with riding coordinates:
 N2(H2A), C5(H5), C6(H6), C8(H8), C10(H10), C11(H11), C15(H15), C16(H16),
 C17(H17), C18(H18), C19(H19), C22(H22), C23(H23), C25(H25), C26(H26), C27(H27),
  C28(H28), C32(H32), C33(H33), C34(H34), C35(H35)
3.c Idealised Me refined as rotating group:
 C36(H36A,H36B,H36C), C38(H38A,H38B,H38C), C39(H39A,H39B,H39C)
3.d Idealised tetrahedral OH refined as rotating group:
 O2(H2), O3(H3)
;
_shelx_res_checksum              64522
_olex2_submission_special_instructions 'No special instructions were received'