Gallium Bromide-Promoted Dearomative Indole Insertion in 3-Indolylmethanols: Chemoselective and (Z/E)-Selective Synthesis of 3,3'-Bisindole Derivatives.
Wang, Cong-Shuai; Fan, Tao; Zhang, Hong-Hao; Li, Can; Shen, Yang; Mei, Guang-Jian; Shi, Feng; The Journal of organic chemistry 81 (2016) 11734–11742; doi:10.1021/acs.joc.6b02201

data_4037403
_publ_section_title
;
 Gallium Bromide-Promoted Dearomative Indole Insertion in
 3-Indolylmethanols: Chemoselective and (Z/E)-Selective Synthesis of
 3,3'-Bisindole Derivatives.
;
_journal_issue                   23
_journal_name_full               'The Journal of organic chemistry'
_journal_page_first              11734
_journal_page_last               11742
_journal_paper_doi               10.1021/acs.joc.6b02201
_journal_volume                  81
_journal_year                    2016
_chemical_absolute_configuration ad
_chemical_formula_sum            'C26 H21 N3 O'
_chemical_formula_weight         391.46
_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'
_atom_sites_solution_hydrogens   geom
_audit_creation_method           SHELXL-2014
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   9.2510(11)
_cell_length_b                   11.3325(13)
_cell_length_c                   20.531(2)
_cell_measurement_reflns_used    5267
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      24.32
_cell_measurement_theta_min      2.41
_cell_volume                     2152.4(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-2014 (Sheldrick, 2014)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      296(2)
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.957
_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  0.0256
_diffrn_reflns_av_unetI/netI     0.0267
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.957
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       24
_diffrn_reflns_limit_l_min       -24
_diffrn_reflns_number            16741
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.931
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.182
_diffrn_reflns_theta_min         2.677
_exptl_absorpt_coefficient_mu    0.075
_exptl_absorpt_correction_T_max  0.7461
_exptl_absorpt_correction_T_min  0.6923
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   sadabs
_exptl_crystal_colour            red
_exptl_crystal_density_diffrn    1.208
_exptl_crystal_F_000             824
_exptl_crystal_size_max          0.220
_exptl_crystal_size_mid          0.200
_exptl_crystal_size_min          0.165
_refine_diff_density_max         0.151
_refine_diff_density_min         -0.167
_refine_diff_density_rms         0.042
_refine_ls_abs_structure_details
; 
 Flack x determined using 1272 quotients [(I+)-(I-)]/[(I+)+(I-)] 
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259). 
;
_refine_ls_abs_structure_Flack   0.0(7)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.057
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     273
_refine_ls_number_reflns         4462
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.057
_refine_ls_R_factor_all          0.0596
_refine_ls_R_factor_gt           0.0396
_refine_ls_shift/su_max          0.014
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0602P)^2^+0.0625P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0979
_refine_ls_wR_factor_ref         0.1095
_reflns_Friedel_coverage         0.712
_reflns_Friedel_fraction_full    0.999
_reflns_Friedel_fraction_max     0.898
_reflns_number_gt                3436
_reflns_number_total             4462
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            jo6b02201_si_003.cif
_cod_data_source_block           SF140708_ZHH_0m
_cod_database_code               4037403
_shelx_estimated_absorpt_t_min   0.984
_shelx_estimated_absorpt_t_max   0.988
_shelxl_version_number           2014-3
_shelx_res_checksum              34065
_shelx_hkl_checksum              98942