Green carbon disulfide surrogateviaa combination of potassium sulfide and chloroform for benzothiazine-thione and benzothiazole-thione construction
Tan, Wei; Wang, Cuihong; Jiang, Xuefeng; Organic Chemistry Frontiers 5 (2018) 2390–; doi:10.1039/C8QO00481A

data_1554356
_publ_section_title
;
 Green carbon disulfide surrogateviaa combination of potassium sulfide and
 chloroform for benzothiazine-thione and benzothiazole-thione construction
;
_journal_issue                   15
_journal_name_full               'Organic Chemistry Frontiers'
_journal_page_first              2390
_journal_paper_doi               10.1039/C8QO00481A
_journal_volume                  5
_journal_year                    2018
_chemical_formula_moiety         'C14 H11 N S2'
_chemical_formula_sum            'C14 H11 N S2'
_chemical_formula_weight         257.36
_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'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_block_doi                 10.5517/ccdc.csd.cc1yzm8t
_audit_creation_date             2017-12-22
_audit_creation_method
;
Olex2 1.2
(compiled 2017.08.10 svn.r3458 for OlexSys, GUI svn.r5381)
;
_audit_update_record
;
2018-01-15 deposited with the CCDC.
2018-07-02 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 94.546(2)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   7.26150(10)
_cell_length_b                   11.8328(2)
_cell_length_c                   14.2292(3)
_cell_measurement_reflns_used    7264
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      73.8950
_cell_measurement_theta_min      6.2570
_cell_volume                     1218.78(4)
_computing_cell_refinement       'CrysAlisPro 1.171.39.32a (Rigaku OD, 2017)'
_computing_data_collection       'CrysAlisPro 1.171.39.32a (Rigaku OD, 2017)'
_computing_data_reduction        'CrysAlisPro 1.171.39.32a (Rigaku OD, 2017)'
_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      293(2)
_diffrn_detector                 'CCD plate'
_diffrn_measured_fraction_theta_full 0.988
_diffrn_measured_fraction_theta_max 0.988
_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    -30.00  21.00   1.00    2.00    --    0.00  77.00  90.00   51
  2  \w     13.00  58.00   1.00    2.00    --    0.00  38.00  60.00   45
  3  \w    -14.00  12.00   1.00    2.00    --    0.00  38.00 -60.00   26
  4  \w     31.00  89.00   1.00    2.00    --    0.00  77.00  90.00   58
  5  \w    -18.00  10.00   1.00    2.00    --    0.00  38.00  60.00   28
  6  \w     55.00  87.00   1.00    2.00    --    0.00  38.00 -30.00   32
  7  \w     50.00  78.00   1.00    2.00    --    0.00  38.00 -60.00   28
  8  \w     -1.00  26.00   1.00    2.00    --    0.00  38.00 -30.00   27
  9  \w     13.00 126.00   1.00    4.00    --   95.80 -82.00   0.00  113
 10  \w     39.00  85.00   1.00    4.00    --   95.80 -77.00-150.00   46
 11  \w     61.00 113.00   1.00    4.00    --   95.80 -30.00-180.00   52
 12  \w     89.00 115.00   1.00    4.00    --   95.80 -77.00-150.00   26
 13  \w     32.00 127.00   1.00    4.00    --   95.80 -82.00 150.00   95
 14  \w     22.00  47.00   1.00    4.00    --   95.80 -82.00 -90.00   25
 15  \w      6.00  53.00   1.00    4.00    --   95.80 -30.00-180.00   47
 16  \w     80.00 110.00   1.00    4.00    --   95.80 -77.00  60.00   30
 17  \w      6.00  36.00   1.00    4.00    --   95.80 -77.00  60.00   30
 18  \w      6.00 116.00   1.00    4.00    --   95.80 -61.00   0.00  110
 19  \w     23.00 119.00   1.00    4.00    --   95.80 -15.00  60.00   96
 20  \w     80.00 106.00   1.00    4.00    --   95.80 -82.00 -90.00   26
 21  \w     20.00  73.00   1.00    4.00    --   95.80 -77.00 -30.00   53
 22  \w     68.00 182.00   1.00    4.00    --   95.80   0.00 150.00  114
 23  \w     34.00  60.00   1.00    4.00    --   95.80 -82.00-180.00   26
 24  \w     81.00 106.00   1.00    4.00    --   95.80 -82.00-180.00   25
 25  \w    153.00 178.00   1.00    4.00    --   95.80  30.00-150.00   25
 26  \w      6.00  46.00   1.00    4.00    --   95.80   0.00 150.00   40
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB AFC12 (RINC): Kappa dual home/near'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0342936000
_diffrn_orient_matrix_UB_12      0.1278995000
_diffrn_orient_matrix_UB_13      -0.0086031000
_diffrn_orient_matrix_UB_21      0.1538707000
_diffrn_orient_matrix_UB_22      -0.0072866000
_diffrn_orient_matrix_UB_23      0.0806978000
_diffrn_orient_matrix_UB_31      0.1429623000
_diffrn_orient_matrix_UB_32      -0.0231936000
_diffrn_orient_matrix_UB_33      -0.0721766000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0310
_diffrn_reflns_av_unetI/netI     0.0204
_diffrn_reflns_Laue_measured_fraction_full 0.988
_diffrn_reflns_Laue_measured_fraction_max 0.988
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            10496
_diffrn_reflns_point_group_measured_fraction_full 0.988
_diffrn_reflns_point_group_measured_fraction_max 0.988
_diffrn_reflns_theta_full        67.070
_diffrn_reflns_theta_max         67.070
_diffrn_reflns_theta_min         4.867
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_source_type              'Enhance (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    3.734
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.60000
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.39.32a (Rigaku Oxford Diffraction, 2017)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            'clear light colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.403
_exptl_crystal_description       block
_exptl_crystal_F_000             536
_exptl_crystal_size_max          0.25
_exptl_crystal_size_mid          0.24
_exptl_crystal_size_min          0.21
_refine_diff_density_max         0.178
_refine_diff_density_min         -0.241
_refine_diff_density_rms         0.046
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.071
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     154
_refine_ls_number_reflns         2151
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.071
_refine_ls_R_factor_all          0.0363
_refine_ls_R_factor_gt           0.0343
_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^)+(0.0540P)^2^+0.3000P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0940
_refine_ls_wR_factor_ref         0.0954
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2008
_reflns_number_total             2151
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c8qo00481a2.cif
_cod_data_source_block           exp_170
_cod_database_code               1554356
_shelx_shelxl_version_number     2016/6
_reflns_odcompleteness_completeness 99.65
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
2.a Secondary CH2 refined with riding coordinates:
 C7(H7A,H7B)
2.b Aromatic/amide H refined with riding coordinates:
 C13(H13), C5(H5), C12(H12), C10(H10), C1(H1), C11(H11), C4(H4), C3(H3), C2(H2)
;
_shelx_res_checksum              44328
_shelx_hkl_checksum              45573
_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 1.679
_oxdiff_exptl_absorpt_empirical_full_min 0.751