Oxidative Coupling of Carbazoles: A Substituent-Governed Regioselectivity Profile.
Mallick, Sudesh; Maddala, Sudhakar; Kollimalayan, Kalidass; Venkatakrishnan, Parthasarathy; The Journal of organic chemistry 84 (2019) 73–93; doi:10.1021/acs.joc.8b02322

data_4035892
_publ_section_title
;
 Oxidative Coupling of Carbazoles: A Substituent-Governed Regioselectivity
 Profile.
;
_journal_issue                   1
_journal_name_full               'The Journal of organic chemistry'
_journal_page_first              73
_journal_page_last               93
_journal_paper_doi               10.1021/acs.joc.8b02322
_journal_volume                  84
_journal_year                    2019
_chemical_formula_sum            'C18 H19 Br N'
_chemical_formula_weight         329.25
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_space_group_name_Hall           '-P 2ybc'
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_atom_sites_solution_hydrogens   geom
_audit_creation_method           SHELXL-2014/7
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_cell_angle_beta                 90.1024(19)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   7.5531(3)
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_cell_length_c                   13.9311(6)
_cell_measurement_reflns_used    5133
_cell_measurement_temperature    296(2)
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_cell_measurement_theta_min      2.70
_cell_volume                     1515.02(11)
_computing_cell_refinement       'Bruker SAINT'
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_computing_structure_solution    'SHELXS-97 (Sheldrick 2008)'
_diffrn_ambient_temperature      296(2)
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       '\f and \w scans'
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_diffrn_reflns_av_R_equivalents  0.0291
_diffrn_reflns_av_unetI/netI     0.0268
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
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_diffrn_reflns_limit_k_min       -17
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_diffrn_reflns_limit_l_min       -16
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_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 1.000
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_diffrn_reflns_theta_max         24.997
_diffrn_reflns_theta_min         2.034
_exptl_absorpt_coefficient_mu    2.703
_exptl_absorpt_correction_T_max  0.774
_exptl_absorpt_correction_T_min  0.551
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS V2014/5(Bruker AXS.Inc)'
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.444
_exptl_crystal_description       Block
_exptl_crystal_F_000             676
_exptl_crystal_size_max          0.250
_exptl_crystal_size_mid          0.220
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_refine_diff_density_max         0.281
_refine_diff_density_min         -0.413
_refine_diff_density_rms         0.061
_refine_ls_extinction_method     none
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_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     182
_refine_ls_number_reflns         2661
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.045
_refine_ls_R_factor_all          0.0469
_refine_ls_R_factor_gt           0.0319
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0426P)^2^+0.8782P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0791
_refine_ls_wR_factor_ref         0.0859
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2153
_reflns_number_total             2661
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            jo8b02322_si_003.cif
_cod_data_source_block           10
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               4035892
_shelx_shelxl_version_number     2014/7
_shelx_estimated_absorpt_t_min   0.551
_shelx_estimated_absorpt_t_max   0.774
_shelx_res_checksum              55351
_shelx_hkl_checksum              24559