Dehydrogenative Aromatic Ring Fusion for Carbazole Synthesis via C-C/C-N Bond Formation and Alkyl Migration.
Maiti, Saikat; Mal, Prasenjit; Organic letters 19 (2017) 2454–2457; doi:10.1021/acs.orglett.7b01117

data_1546230
_publ_section_title
;
 Dehydrogenative Aromatic Ring Fusion for Carbazole Synthesis via C-C/C-N
 Bond Formation and Alkyl Migration.
;
_journal_issue                   9
_journal_name_full               'Organic letters'
_journal_page_first              2454
_journal_page_last               2457
_journal_paper_doi               10.1021/acs.orglett.7b01117
_journal_volume                  19
_journal_year                    2017
_chemical_formula_moiety         'C25 H27 N O2 S'
_chemical_formula_sum            'C25 H27 N O2 S'
_chemical_formula_weight         405.53
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     direct
_audit_creation_date             2016-08-10
_audit_creation_method
;
Olex2 1.2-beta
(compiled 2016.02.19 svn.r3266 for OlexSys, GUI svn.r5155)
;
_cell_angle_alpha                109.313(4)
_cell_angle_beta                 100.073(4)
_cell_angle_gamma                97.026(4)
_cell_formula_units_Z            2
_cell_length_a                   5.9068(3)
_cell_length_b                   13.7441(7)
_cell_length_c                   14.5687(8)
_cell_measurement_reflns_used    4869
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      25.96
_cell_measurement_theta_min      2.88
_cell_volume                     1078.12(11)
_computing_cell_refinement       'SAINT v8.34A (Bruker, 2013)'
_computing_data_reduction        'SAINT v8.34A (Bruker, 2013)'
_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    'SIR2004 (Burla et al., 2007)'
_diffrn_ambient_temperature      296.15
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.996
_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
_diffrn_reflns_av_unetI/netI     0.0317
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            14079
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.996
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.052
_diffrn_reflns_theta_min         2.884
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.171
_exptl_absorpt_correction_T_max  0.7453
_exptl_absorpt_correction_T_min  0.6085
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2014/5 (Bruker,2014/5) was used for absorption correction.
wR2(int) was 0.1009 before and 0.0432 after correction.
The Ratio of minimum to maximum transmission is 0.8164.
The \l/2 correction factor is 0.00150.
;
_exptl_crystal_colour            'clear colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.249
_exptl_crystal_description       block
_exptl_crystal_F_000             432
_exptl_crystal_size_max          0.36
_exptl_crystal_size_mid          0.27
_exptl_crystal_size_min          0.22
_refine_diff_density_max         0.237
_refine_diff_density_min         -0.333
_refine_diff_density_rms         0.041
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.031
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     280
_refine_ls_number_reflns         4243
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.031
_refine_ls_R_factor_all          0.0558
_refine_ls_R_factor_gt           0.0433
_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^)+(0.0556P)^2^+0.3865P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1106
_refine_ls_wR_factor_ref         0.1185
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3394
_reflns_number_total             4243
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            ol7b01117_si_003.cif
_cod_data_source_block           mb_sm_541
_cod_original_cell_volume        1078.12(10)
_cod_database_code               1546230
_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:
 C18(H18), C9(H9), C20(H20), C11(H11), C12(H12), C7(H7)
2.b Idealised Me refined as rotating group:
 C23(H23A,H23B,H23C), C14(H14A,H14B,H14C), C25(H25A,H25B,H25C), C22(H22A,H22B,
 H22C), C24(H24A,H24B,H24C), C15(H15A,H15B,H15C)
;
_shelx_res_checksum              378
_shelx_hkl_checksum              49282
_shelx_shelxl_version_number     2014/7
_olex2_submission_special_instructions 'No special instructions were received'