Direct access to bis-S-heterocycles via copper-catalyzed three component tandem cyclization using S<sub>8</sub> as a sulfur source.
Zhou, Peiqi; Huang, Yubing; Wu, Wanqing; Yu, Wentao; Li, Jianxiao; Zhu, Zhongzhi; Jiang, Huanfeng; Organic & biomolecular chemistry 17 (2019) 3424–3432; doi:10.1039/c9ob00377k

data_7156719
_publ_section_title
;
 Direct access to bis-S-heterocycles via copper-catalyzed three component
 tandem cyclization using S<sub>8</sub> as a sulfur source.
;
_journal_issue                   13
_journal_name_full               'Organic &amp; biomolecular chemistry'
_journal_page_first              3424
_journal_page_last               3432
_journal_paper_doi               10.1039/c9ob00377k
_journal_volume                  17
_journal_year                    2019
_chemical_formula_moiety         'C15 H8 Br N S2'
_chemical_formula_sum            'C15 H8 Br N S2'
_chemical_formula_weight         346.25
_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   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2018-05-02
_audit_creation_method
;
Olex2 1.2
(compiled 2018.04.26 svn.r3504 for OlexSys, GUI svn.r5492)
;
_audit_update_record
;
2018-09-11 deposited with the CCDC.    2019-03-04 downloaded from the CCDC.
;
_cell_angle_alpha                88.344(3)
_cell_angle_beta                 89.963(3)
_cell_angle_gamma                79.153(4)
_cell_formula_units_Z            2
_cell_length_a                   6.8836(3)
_cell_length_b                   7.0346(3)
_cell_length_c                   13.5790(5)
_cell_measurement_reflns_used    6044
_cell_measurement_temperature    100.00(10)
_cell_measurement_theta_max      29.3270
_cell_measurement_theta_min      2.9210
_cell_volume                     645.52(5)
_computing_cell_refinement       'CrysAlisPro 1.171.38.43f (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.38.43f (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.43f (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    'ShelXT (Sheldrick, 2015)'
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      100.00(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 5.2684
_diffrn_detector_type            AtlasS2
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_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    -85.00  17.00   1.00    1.00    --  -11.59 -57.00 -60.00  102
  2  \w    -40.00  62.00   1.00    1.00    --  -11.59  57.00  90.00  102
  3  \w    -21.00  88.00   1.00    1.00    --   11.74  77.00-150.00  109
  4  \w     34.00  99.00   1.00    1.00    --   11.74-178.00  90.00   65
  5  \w    -20.00   5.00   1.00    1.00    --   11.74 -99.00-150.00   25
  6  \w    -63.00  36.00   1.00    1.00    --   11.74 -37.00-120.00   99
  7  \w    -85.00 -60.00   1.00    1.00    --  -11.59 151.00 -82.45   25
  8  \w    -88.00 -18.00   1.00    1.00    --  -11.59 -77.00 150.00   70
  9  \w    -85.00 -39.00   1.00    1.00    --  -11.59 151.00 133.38   46
 10  \w     23.00  52.00   1.00    1.00    --   11.74  37.00  90.00   29
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, AtlasS2'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0076339000
_diffrn_orient_matrix_UB_12      -0.0015222000
_diffrn_orient_matrix_UB_13      -0.0520763000
_diffrn_orient_matrix_UB_21      -0.1022269000
_diffrn_orient_matrix_UB_22      0.0403657000
_diffrn_orient_matrix_UB_23      -0.0042970000
_diffrn_orient_matrix_UB_31      0.0223396000
_diffrn_orient_matrix_UB_32      0.0944316000
_diffrn_orient_matrix_UB_33      -0.0006682000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0447
_diffrn_reflns_av_unetI/netI     0.0370
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            9909
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_theta_full        24.993
_diffrn_reflns_theta_max         24.993
_diffrn_reflns_theta_min         2.950
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    3.489
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.36968
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.38.43f (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    1.781
_exptl_crystal_description       block
_exptl_crystal_F_000             344
_exptl_crystal_size_max          0.13
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.11
_refine_diff_density_max         0.490
_refine_diff_density_min         -0.506
_refine_diff_density_rms         0.089
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.086
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     172
_refine_ls_number_reflns         2276
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.086
_refine_ls_R_factor_all          0.0289
_refine_ls_R_factor_gt           0.0268
_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^)+(0.0325P)^2^+0.1415P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0644
_refine_ls_wR_factor_ref         0.0657
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2140
_reflns_number_total             2276
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c9ob00377k2.cif
_cod_data_source_block           2pq-1
_cod_depositor_comments
'Adding full bibliography for 7156719--7156720.cif.'
_cod_database_code               7156719
_shelx_shelxl_version_number     2017/1
_reflns_odcompleteness_completeness 99.96
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     26.32
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C5(H5), C12(H12), C6(H6), C2(H2), C15(H15), C3(H3), C13(H13), C14(H14)
;
_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
- Detector area scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 2.106
_oxdiff_exptl_absorpt_empirical_full_min 0.615