Catalytic Asymmetric Synthesis of 3,3'-Bisindoles Bearing Single Axial Chirality.
Chen, Ke-Wei; Wang, Zhao-Shan; Wu, Ping; Yan, Xin-Yu; Zhang, Shu; Zhang, Yu-Chen; Shi, Feng; The Journal of organic chemistry  (2020) –; doi:10.1021/acs.joc.0c01528

data_4038623
_publ_section_title
;
 Catalytic Asymmetric Synthesis of 3,3'-Bisindoles Bearing Single Axial
 Chirality.
;
_journal_name_full               'The Journal of organic chemistry'
_journal_paper_doi               10.1021/acs.joc.0c01528
_journal_year                    2020
_chemical_absolute_configuration rmad
_chemical_formula_moiety         'C46 H30 F N3 O2, C3 H6 O'
_chemical_formula_sum            'C49 H36 F N3 O3'
_chemical_formula_weight         733.81
_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   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2019-07-09
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_cell_angle_alpha                104.8820(10)
_cell_angle_beta                 91.1700(10)
_cell_angle_gamma                90.2450(10)
_cell_formula_units_Z            4
_cell_length_a                   12.9213(3)
_cell_length_b                   16.0170(3)
_cell_length_c                   20.8553(4)
_cell_measurement_reflns_used    9303
_cell_measurement_temperature    170(2)
_cell_measurement_theta_max      52.58
_cell_measurement_theta_min      3.501
_cell_volume                     4170.37(15)
_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 0.999
_diffrn_measured_fraction_theta_max 0.994
_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  0.0459
_diffrn_reflns_av_unetI/netI     0.0588
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.994
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_k_max       19
_diffrn_reflns_limit_k_min       -19
_diffrn_reflns_limit_l_max       25
_diffrn_reflns_limit_l_min       -25
_diffrn_reflns_number            75915
_diffrn_reflns_point_group_measured_fraction_full 0.984
_diffrn_reflns_point_group_measured_fraction_max 0.976
_diffrn_reflns_theta_full        53.594
_diffrn_reflns_theta_max         55.045
_diffrn_reflns_theta_min         2.715
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.392
_exptl_absorpt_correction_T_max  0.7508
_exptl_absorpt_correction_T_min  0.6032
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
'SADABS-2016/2 (Bruker,2016/2) was used for absorption correction. wR2(int) was 0.1176 before and 0.0617 after correction. The Ratio of minimum to maximum transmission is 0.8034. The \l/2 correction factor is Not present.'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.169
_exptl_crystal_description       block
_exptl_crystal_F_000             1536
_exptl_crystal_size_max          0.1
_exptl_crystal_size_mid          0.08
_exptl_crystal_size_min          0.03
_refine_diff_density_max         0.336
_refine_diff_density_min         -0.239
_refine_diff_density_rms         0.039
_refine_ls_abs_structure_details
;
 Flack x determined using 8978 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.07(7)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.033
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     2025
_refine_ls_number_reflns         31113
_refine_ls_number_restraints     3
_refine_ls_restrained_S_all      1.033
_refine_ls_R_factor_all          0.0736
_refine_ls_R_factor_gt           0.0508
_refine_ls_shift/su_max          0.003
_refine_ls_shift/su_mean         0.001
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0617P)^2^+0.2732P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1147
_refine_ls_wR_factor_ref         0.1286
_reflns_Friedel_coverage         0.965
_reflns_Friedel_fraction_full    0.969
_reflns_Friedel_fraction_max     0.958
_reflns_number_gt                23633
_reflns_number_total             31113
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            jo0c01528_si_002.cif
_cod_data_source_block           190709sf_0m
_cod_database_code               4038623
_shelx_shelxl_version_number     2016/6
_shelx_estimated_absorpt_t_max   0.988
_shelx_estimated_absorpt_t_min   0.962
_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 Ternary CH refined with riding coordinates:
 C34(H34), C34A(H34A), C34B(H34B), C34C(H34C)
2.b Aromatic/amide H refined with riding coordinates:
 N1(H1), N2(H2), N3(H3), C3(H3A), C5(H5), C6(H6), C7(H7), C8(H8), C12(H12),
 C13(H13), C14(H14), C15(H15), C21(H21), C23(H23), C24(H24), C28(H28), C29(H29),
  C30(H30), C31(H31), C36(H36), C37(H37), C38(H38), C39(H39), C40(H40),
 C42(H42), C43(H43), C44(H44), C45(H45), C46(H46), N1A(H1A), N2A(H2A),
 N3A(H3AA), C3A(H3AB), C5A(H5A), C6A(H6A), C7A(H7A), C8A(H8A), C12A(H12A),
 C13A(H13A), C14A(H14A), C15A(H15A), C21A(H21A), C23A(H23A), C24A(H24A),
 C28A(H28A), C29A(H29A), C30A(H30A), C31A(H31A), C36A(H36A), C37A(H37A),
 C38A(H38A), C39A(H39A), C40A(H40A), C42A(H42A), C43A(H43A), C44A(H44A),
 C45A(H45A), C46A(H46A), N1B(H1B), N2B(H2B), N3B(H3B), C3B(H3BA), C5B(H5B),
 C6B(H6B), C7B(H7B), C8B(H8B), C12B(H12B), C13B(H13B), C14B(H14B), C15B(H15B),
 C20B(H20B), C21B(H21B), C23B(H23B), C28B(H28B), C29B(H29B), C30B(H30B),
 C31B(H31B), C36B(H36B), C37B(H37B), C38B(H38B), C39B(H39B), C40B(H40B),
 C42B(H42B), C43B(H43B), C44B(H44B), C45B(H45B), C46B(H46B), N1C(H1C), N2C(H2C),
  N3C(H3C), C3C(H3CA), C5C(H5C), C6C(H6C), C7C(H7C), C8C(H8C), C12C(H12C),
 C13C(H13C), C14C(H14C), C15C(H15C), C21C(H21C), C23C(H23C), C24C(H24C),
 C28C(H28C), C29C(H29C), C30C(H30C), C31C(H31C), C36C(H36C), C37C(H37C),
 C38C(H38C), C39C(H39C), C40C(H40C), C42C(H42C), C43C(H43C), C44C(H44C),
 C45C(H45C), C46C(H46C)
2.c Idealised Me refined as rotating group:
 C1S(H1SA,H1SB,H1SC), C3S(H3SA,H3SB,H3SC), C4S(H4SA,H4SB,H4SC), C6S(H6SA,H6SB,
 H6SC), C10S(H10A,H10B,H10C), C12S(H12D,H12E,H12F), C7S(H7SA,H7SB,H7SC),
 C9S(H9SA,H9SB,H9SC)
;
_shelx_res_checksum              36462
_shelx_hkl_checksum              87542
_shelx_fab_checksum              36246
_olex2_submission_special_instructions 'No special instructions were received'