Silver-copper co-catalyzed cascade intramolecular cyclization/desulfinamide/dehydrogenation: one-pot synthesis of substituted carbazoles.
Huang, Yuanqiong; Guo, Zhonglin; Song, Hongjian; Liu, Yuxiu; Wang, Qingmin; Chemical communications (Cambridge, England) 54 (2018) 7143–7146; doi:10.1039/c8cc03600d

data_7121769
_publ_section_title
;
 Silver-copper co-catalyzed cascade intramolecular
 cyclization/desulfinamide/dehydrogenation: one-pot synthesis of
 substituted carbazoles.
;
_journal_issue                   52
_journal_name_full               'Chemical communications (Cambridge, England)'
_journal_page_first              7143
_journal_page_last               7146
_journal_paper_doi               10.1039/c8cc03600d
_journal_volume                  54
_journal_year                    2018
_chemical_formula_moiety         'C19 H15 N O3 S'
_chemical_formula_sum            'C19 H15 N O3 S'
_chemical_formula_weight         337.38
_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'
_symmetry_space_group_name_Hall  '-P 2yn'
_symmetry_space_group_name_H-M   'P 1 21/n 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_audit_creation_date             2018-03-06
_audit_creation_method
;
Olex2 1.2
(compiled 2017.08.10 svn.r3458 for OlexSys, GUI svn.r5381)
;
_audit_update_record
;
2018-03-06 deposited with the CCDC.
2018-05-29 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 99.753(2)
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   17.5290(4)
_cell_length_b                   10.1840(2)
_cell_length_c                   18.2727(4)
_cell_measurement_reflns_used    11241
_cell_measurement_temperature    113(2)
_cell_measurement_theta_max      30.8060
_cell_measurement_theta_min      3.5360
_cell_volume                     3214.81(12)
_computing_cell_refinement       'CrysAlisPro 1.171.39.28b (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.39.28b (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.39.28b (Rigaku OD, 2015)'
_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    'ShelXS (Sheldrick, 2008)'
_diffrn_ambient_temperature      113.15
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 5.814
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_details
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  t~exp~   \w     \q     \k     \f   Frames
  1  \w   -120.00  60.00   0.50    8.00    --  -30.00  45.00   0.00  360
  2  \w   -120.00  60.00   0.50    8.00    --  -30.00  45.00  90.00  360
  3  \w   -120.00  60.00   0.50    8.00    --  -30.00  45.00 180.00  360
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB AFC10 (RCD3): fixed-chi single'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0404697000
_diffrn_orient_matrix_UB_12      0.0091663000
_diffrn_orient_matrix_UB_13      0.0105725000
_diffrn_orient_matrix_UB_21      -0.0027418000
_diffrn_orient_matrix_UB_22      -0.0174611000
_diffrn_orient_matrix_UB_23      0.0370288000
_diffrn_orient_matrix_UB_31      0.0063107000
_diffrn_orient_matrix_UB_32      -0.0668264000
_diffrn_orient_matrix_UB_33      -0.0082423000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0390
_diffrn_reflns_av_unetI/netI     0.0280
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       23
_diffrn_reflns_limit_h_min       -23
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       24
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_number            32252
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.878
_diffrn_reflns_theta_min         3.527
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_source_type              'Enhance (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    0.218
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.73355
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.39.28b (Rigaku Oxford Diffraction, 2015)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.394
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             1408
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.18
_exptl_crystal_size_min          0.12
_refine_diff_density_max         0.172
_refine_diff_density_min         -0.336
_refine_diff_density_rms         0.038
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.044
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     435
_refine_ls_number_reflns         7652
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.044
_refine_ls_R_factor_all          0.0520
_refine_ls_R_factor_gt           0.0395
_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^)+(0.0546P)^2^+0.6439P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1065
_refine_ls_wR_factor_ref         0.1141
_reflns_Friedel_coverage         0.000
_reflns_number_gt                6071
_reflns_number_total             7652
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c8cc03600d2.cif
_cod_data_source_block           m20180117a
_cod_depositor_comments          'Adding full bibliography for 7121769.cif.'
_cod_original_cell_volume        3214.79(13)
_cod_database_code               7121769
_shelx_shelxl_version_number     2017/1
_shelx_estimated_absorpt_t_max   0.974
_shelx_estimated_absorpt_t_min   0.958
_reflns_odcompleteness_completeness 99.66
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     26.32
_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:
 C2(H2), C3(H3), C4(H4), C5(H5), C8(H8), C9(H9), C10(H10), C11(H11), C14(H14),
 C15(H15), C17(H17), C18(H18), C21(H21), C22(H22), C23(H23), C24(H24), C27(H27),
  C28(H28), C29(H29), C30(H30), C33(H33), C34(H34), C36(H36), C37(H37)
2.b Idealised Me refined as rotating group:
 C19(H19A,H19B,H19C), C38(H38A,H38B,H38C)
;
_shelx_res_checksum              58418
_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.509
_oxdiff_exptl_absorpt_empirical_full_min 0.712