Metal-Free Indole-Phenacyl Bromide Cyclization: A Regioselective Synthesis of 3,5-Diarylcarbazoles.
Debnath, Sudipto; Das, Tuluma; Pati, Tanmay K.; Majumdar, Swapan; Maiti, Dilip K.; The Journal of organic chemistry 85 (2020) 13272–13279; doi:10.1021/acs.joc.0c01670

data_4038863
_publ_section_title
;
 Metal-Free Indole-Phenacyl Bromide Cyclization: A Regioselective
 Synthesis of 3,5-Diarylcarbazoles.
;
_journal_issue                   20
_journal_name_full               'The Journal of organic chemistry'
_journal_page_first              13272
_journal_page_last               13279
_journal_paper_doi               10.1021/acs.joc.0c01670
_journal_volume                  85
_journal_year                    2020
_chemical_formula_moiety         'C26 H21 N O2'
_chemical_formula_sum            'C26 H21 N O2'
_chemical_formula_weight         379.45
_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'
_atom_sites_solution_hydrogens   geom
_audit_creation_method           SHELXL-2014/7
_cell_angle_alpha                90
_cell_angle_beta                 106.897(4)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   10.676(4)
_cell_length_b                   8.467(3)
_cell_length_c                   11.173(4)
_cell_measurement_reflns_used    1936
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      21.66
_cell_measurement_theta_min      3.07
_cell_volume                     966.4(6)
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_diffrn_ambient_temperature      296(2)
_diffrn_measured_fraction_theta_full 0.994
_diffrn_measured_fraction_theta_max 0.994
_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  0.0338
_diffrn_reflns_av_unetI/netI     0.0389
_diffrn_reflns_Laue_measured_fraction_full 0.994
_diffrn_reflns_Laue_measured_fraction_max 0.994
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            5350
_diffrn_reflns_point_group_measured_fraction_full 0.918
_diffrn_reflns_point_group_measured_fraction_max 0.918
_diffrn_reflns_theta_full        24.526
_diffrn_reflns_theta_max         24.526
_diffrn_reflns_theta_min         1.905
_diffrn_source                   'sealed tube'
_exptl_absorpt_coefficient_mu    0.082
_exptl_absorpt_correction_T_max  0.9694
_exptl_absorpt_correction_T_min  0.9443
_exptl_absorpt_correction_type   multi-scan
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.305
_exptl_crystal_description       crystalline
_exptl_crystal_F_000             400
_exptl_crystal_size_max          0.90
_exptl_crystal_size_mid          0.71
_exptl_crystal_size_min          0.51
_refine_diff_density_max         0.194
_refine_diff_density_min         -0.117
_refine_diff_density_rms         0.029
_refine_ls_abs_structure_details
;
 Flack x determined using 759 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.5(10)
_refine_ls_extinction_coef       0.017(4)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2014/7 (Sheldrick 2014'
_refine_ls_goodness_of_fit_ref   0.846
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     265
_refine_ls_number_reflns         2315
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      0.845
_refine_ls_R_factor_all          0.0422
_refine_ls_R_factor_gt           0.0358
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0709P)^2^+0.1383P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0915
_refine_ls_wR_factor_ref         0.0983
_reflns_Friedel_coverage         0.706
_reflns_Friedel_fraction_full    0.828
_reflns_Friedel_fraction_max     0.828
_reflns_number_gt                2051
_reflns_number_total             2315
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            jo0c01670_si_002.cif
_cod_data_source_block           td2_253
_cod_depositor_comments          'Adding full bibliography for 4038863.cif.'
_cod_original_sg_symbol_H-M      'P 21'
_cod_database_code               4038863
_shelx_shelxl_version_number     2014/7
_shelx_res_checksum              62878
_shelx_hkl_checksum              18664