Oxidative N-Arylation for Carbazole Synthesis by C-C Bond Activation.
Maiti, Saikat; Bose, Anima; Mal, Prasenjit; The Journal of organic chemistry 83 (2018) 8127–8138; doi:10.1021/acs.joc.8b00921

data_4035581
_publ_section_title
;
 Oxidative N-Arylation for Carbazole Synthesis by C-C Bond Activation.
;
_journal_issue                   15
_journal_name_full               'The Journal of organic chemistry'
_journal_page_first              8127
_journal_page_last               8138
_journal_paper_doi               10.1021/acs.joc.8b00921
_journal_volume                  83
_journal_year                    2018
_chemical_formula_moiety         'C18 H20 Br N O2 S'
_chemical_formula_sum            'C18 H20 Br N O2 S'
_chemical_formula_weight         394.32
_space_group_crystal_system      orthorhombic
_space_group_IT_number           61
_space_group_name_Hall           '-P 2ac 2ab'
_space_group_name_H-M_alt        'P b c a'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_audit_creation_date             2018-04-17
_audit_creation_method
;
Olex2 1.2-alpha
(compiled 2016.02.24 svn.r3266 for OlexSys, GUI svn.r5155)
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   16.2482(3)
_cell_length_b                   8.3987(2)
_cell_length_c                   25.8000(6)
_cell_measurement_reflns_used    1870
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      19.71
_cell_measurement_theta_min      2.40
_cell_volume                     3520.76(13)
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_diffrn_ambient_temperature      296.15
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.995
_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  0.0607
_diffrn_reflns_av_unetI/netI     0.0267
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.995
_diffrn_reflns_limit_h_max       21
_diffrn_reflns_limit_h_min       -21
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       34
_diffrn_reflns_limit_l_min       -34
_diffrn_reflns_number            50582
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.995
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         28.705
_diffrn_reflns_theta_min         2.842
_exptl_absorpt_coefficient_mu    2.462
_exptl_absorpt_correction_T_max  0.7452
_exptl_absorpt_correction_T_min  0.6581
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2008/1 (Bruker,2008) was used for absorption correction.
wR2(int) was 0.0968 before and 0.0740 after correction.
The Ratio of minimum to maximum transmission is 0.8831.
The \l/2 correction factor is 0.0015.
;
_exptl_crystal_colour            'clear whiteish white'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   whiteish
_exptl_crystal_colour_primary    white
_exptl_crystal_density_diffrn    1.488
_exptl_crystal_description       needle
_exptl_crystal_F_000             1616
_exptl_crystal_size_max          0.15
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.1
_refine_diff_density_max         0.356
_refine_diff_density_min         -0.521
_refine_diff_density_rms         0.056
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.011
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     213
_refine_ls_number_reflns         4537
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.011
_refine_ls_R_factor_all          0.0665
_refine_ls_R_factor_gt           0.0356
_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^)+(0.0450P)^2^+1.3320P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0826
_refine_ls_wR_factor_ref         0.0961
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3066
_reflns_number_total             4537
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            jo8b00921_si_002.cif
_cod_data_source_block           pmal_sm_2_764
_cod_original_cell_volume        3520.77(13)
_cod_database_code               4035581
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C9(H9), C11(H11), C5(H5), C2(H2), C3(H3)
2.b Idealised Me refined as rotating group:
 C13(H13A,H13B,H13C), C18(H18A,H18B,H18C), C17(H17A,H17B,H17C), C15(H15A,H15B,
 H15C), C16(H16A,H16B,H16C)
;
_shelx_res_checksum              4210
_shelx_hkl_checksum              13113
_shelx_shelxl_version_number     2016/4
_olex2_submission_special_instructions 'No special instructions were received'