Rh(III)-Catalyzed Asymmetric Synthesis of Axially Chiral Biindolyls by Merging C-H Activation and Nucleophilic Cyclization.
Tian, Miaomiao; Bai, Dachang; Zheng, Guangfan; Chang, Junbiao; Li, Xingwei; Journal of the American Chemical Society 141 (2019) 9527–9532; doi:10.1021/jacs.9b04711

data_4127455
_publ_section_title
;
 Rh(III)-Catalyzed Asymmetric Synthesis of Axially Chiral Biindolyls by
 Merging C-H Activation and Nucleophilic Cyclization.
;
_journal_issue                   24
_journal_name_full               'Journal of the American Chemical Society'
_journal_page_first              9527
_journal_page_last               9532
_journal_paper_doi               10.1021/jacs.9b04711
_journal_volume                  141
_journal_year                    2019
_chemical_absolute_configuration ad
_chemical_formula_sum            'C40 H30 N4 O2 S'
_chemical_formula_weight         630.74
_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   geom
_audit_creation_method           SHELXL-2013
_cell_angle_alpha                90
_cell_angle_beta                 102.7440(10)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   9.4170(3)
_cell_length_b                   10.9955(4)
_cell_length_c                   15.6189(6)
_cell_measurement_reflns_used    9903
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      51.702
_cell_measurement_theta_min      4.569
_cell_volume                     1577.41(10)
_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-2013 (Sheldrick, 2013)'
_computing_structure_solution    'SHELXS-97 (Sheldrick 2008)'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0439
_diffrn_reflns_av_unetI/netI     0.0388
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            24323
_diffrn_reflns_point_group_measured_fraction_full 0.996
_diffrn_reflns_point_group_measured_fraction_max 0.996
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         25.999
_diffrn_reflns_theta_min         2.323
_exptl_absorpt_coefficient_mu    0.146
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_correction_T_min  0.5027
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   sadabs
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.328
_exptl_crystal_description       prismatic
_exptl_crystal_F_000             660
_exptl_crystal_size_max          0.180
_exptl_crystal_size_mid          0.150
_exptl_crystal_size_min          0.130
_refine_diff_density_max         0.143
_refine_diff_density_min         -0.160
_refine_diff_density_rms         0.025
_refine_ls_abs_structure_details
; 
 Flack x determined using 2213 quotients [(I+)-(I-)]/[(I+)+(I-)] 
 (Parsons and Flack (2004), Acta Cryst. A60, s61). 
;
_refine_ls_abs_structure_Flack   -0.02(3)
_refine_ls_extinction_coef       0.032(4)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   1.021
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     426
_refine_ls_number_reflns         6187
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.021
_refine_ls_R_factor_all          0.0450
_refine_ls_R_factor_gt           0.0358
_refine_ls_shift/su_max          0.003
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0466P)^2^+0.1024P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0857
_refine_ls_wR_factor_ref         0.0925
_reflns_Friedel_coverage         0.895
_reflns_Friedel_fraction_full    0.997
_reflns_Friedel_fraction_max     0.997
_reflns_number_gt                5370
_reflns_number_total             6187
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            ja9b04711_si_002.cif
_cod_data_source_block           mo_d8v19327_0m
_cod_database_code               4127455
_shelx_estimated_absorpt_t_min   0.974
_shelx_estimated_absorpt_t_max   0.981
_shelxl_version_number           2013-4
_shelx_res_checksum              8903
_shelx_hkl_checksum              10469