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_7156720
_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         'C16 H8 F3 N S3'
_chemical_formula_sum            'C16 H8 F3 N S3'
_chemical_formula_weight         367.41
_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             2018-06-19
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_audit_update_record
;
2018-09-11 deposited with the CCDC.    2019-03-04 downloaded from the CCDC.
;
_cell_angle_alpha                77.893(5)
_cell_angle_beta                 87.653(5)
_cell_angle_gamma                86.789(5)
_cell_formula_units_Z            2
_cell_length_a                   4.2674(3)
_cell_length_b                   12.9135(8)
_cell_length_c                   13.4730(8)
_cell_measurement_reflns_used    3770
_cell_measurement_temperature    100.00(10)
_cell_measurement_theta_max      29.0520
_cell_measurement_theta_min      2.4690
_cell_volume                     724.48(8)
_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 0.999
_diffrn_measured_fraction_theta_max 0.999
_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    -60.00  40.00   1.00    1.00    --   11.74 -57.00 -90.00  100
  2  \w    -21.00  88.00   1.00    1.00    --   11.74  77.00-180.00  109
  3  \w    -16.00  85.00   1.00    1.00    --   11.74  57.00  60.00  101
  4  \w    -62.00 -15.00   1.00    1.00    --  -11.59 115.00 161.00   47
  5  \w    -16.00  27.00   1.00    1.00    --   11.74  57.00 -60.00   43
;
_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      0.0431084000
_diffrn_orient_matrix_UB_12      0.0406810000
_diffrn_orient_matrix_UB_13      0.0241493000
_diffrn_orient_matrix_UB_21      -0.0023403000
_diffrn_orient_matrix_UB_22      0.0365255000
_diffrn_orient_matrix_UB_23      -0.0473346000
_diffrn_orient_matrix_UB_31      -0.1608564000
_diffrn_orient_matrix_UB_32      0.0131972000
_diffrn_orient_matrix_UB_33      0.0088294000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0275
_diffrn_reflns_av_unetI/netI     0.0387
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       5
_diffrn_reflns_limit_h_min       -5
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            6627
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_theta_full        25.000
_diffrn_reflns_theta_max         25.000
_diffrn_reflns_theta_min         1.990
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    0.541
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.91018
_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            red
_exptl_crystal_colour_primary    red
_exptl_crystal_density_diffrn    1.684
_exptl_crystal_description       block
_exptl_crystal_F_000             372
_exptl_crystal_size_max          0.13
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.11
_refine_diff_density_max         0.448
_refine_diff_density_min         -0.366
_refine_diff_density_rms         0.064
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.055
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     208
_refine_ls_number_reflns         2536
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.055
_refine_ls_R_factor_all          0.0402
_refine_ls_R_factor_gt           0.0350
_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^)+(0.0361P)^2^+0.4797P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0812
_refine_ls_wR_factor_ref         0.0855
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2237
_reflns_number_total             2536
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c9ob00377k2.cif
_cod_data_source_block           3s
_cod_depositor_comments
'Adding full bibliography for 7156719--7156720.cif.'
_cod_database_code               7156720
_shelx_shelxl_version_number     2018/3
_shelx_estimated_absorpt_t_max   0.943
_shelx_estimated_absorpt_t_min   0.933
_reflns_odcompleteness_completeness 99.93
_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), C2(H2), C11(H11), C15(H15), C14(H14), C3(H3), C13(H13), C12(H12)
;
_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 1.187
_oxdiff_exptl_absorpt_empirical_full_min 0.807