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_4037404
_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_formula_sum            'C26 H21 N3 O'
_chemical_formula_weight         391.46
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2yn'
_space_group_name_H-M_alt        'P 1 21/n 1'
_atom_sites_solution_hydrogens   geom
_audit_creation_method           SHELXL-2014
_cell_angle_alpha                90
_cell_angle_beta                 105.516(2)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   10.0804(4)
_cell_length_b                   13.1042(6)
_cell_length_c                   15.9458(7)
_cell_measurement_reflns_used    6183
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      26.81
_cell_measurement_theta_min      3.38
_cell_volume                     2029.60(15)
_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 0.998
_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  0.0308
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_diffrn_reflns_Laue_measured_fraction_full 0.999
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_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -19
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_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.506
_diffrn_reflns_theta_min         2.043
_exptl_absorpt_coefficient_mu    0.080
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_correction_T_min  0.6657
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   SADABS
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.281
_exptl_crystal_F_000             824
_exptl_crystal_size_max          0.260
_exptl_crystal_size_mid          0.220
_exptl_crystal_size_min          0.150
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_refine_ls_extinction_method     none
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_refine_ls_number_reflns         4651
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.061
_refine_ls_R_factor_all          0.0774
_refine_ls_R_factor_gt           0.0490
_refine_ls_shift/su_max          0.009
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0822P)^2^+0.2512P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1306
_refine_ls_wR_factor_ref         0.1539
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3209
_reflns_number_total             4651
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            jo6b02201_si_002.cif
_cod_data_source_block           SF140627_TW_0m
_cod_depositor_comments
;
The following automatic conversions were performed:

data item '_exptl_absorpt_correction_type' value 'MULTI-SCAN' was
changed to 'multi-scan' in accordance with the
/home/saulius/struct/COD-crude-data/automatic-downloads/DataCite-retrospective/ACS/depositions/lib/dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.2 last updated on
2011-04-26.

Automatic conversion script
Id: cif_fix_values 6909 2019-04-08 15:41:33Z antanas 
;
_cod_original_sg_symbol_H-M      'P 21/n'
_cod_database_code               4037404
_shelx_estimated_absorpt_t_min   0.980
_shelx_estimated_absorpt_t_max   0.988
_shelxl_version_number           2014-3
_shelx_res_checksum              46391
_shelx_hkl_checksum              13605