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_1554357
_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         'C15 H13 N S2'
_chemical_formula_sum            'C15 H13 N S2'
_chemical_formula_weight         271.38
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2ybc'
_space_group_name_H-M_alt        'P 1 21/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_block_doi                 10.5517/ccdc.csd.cc1yzmbw
_audit_creation_date             2018-01-09
_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                 95.618(2)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   8.3766(2)
_cell_length_b                   6.28950(10)
_cell_length_c                   25.7206(6)
_cell_measurement_reflns_used    5170
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      73.4510
_cell_measurement_theta_min      5.2880
_cell_volume                     1348.57(5)
_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 0.998
_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     50.00  77.00   1.00    1.00    --    0.00  38.00 -30.00   27
  2  \w    -59.00  -5.00   1.00    1.00    --    0.00 -38.00-150.00   54
  3  \w    -86.00 -55.00   1.00    1.00    --    0.00 -38.00  60.00   31
  4  \w    -49.00  18.00   1.00    1.00    --    0.00 -38.00  60.00   67
  5  \w    -84.00  13.00   1.00    1.00    --    0.00 -38.00 -30.00   97
  6  \w      6.00 118.00   1.00    3.00    --   95.80 -82.00 150.00  112
  7  \w      6.00 100.00   1.00    3.00    --   95.80 -82.00   0.00   94
  8  \w    143.00 185.00   1.00    3.00    --   95.80  61.00  90.00   42
  9  \w      6.00  94.00   1.00    3.00    --   95.80 -30.00  30.00   88
 10  \w     91.00 126.00   1.00    3.00    --   95.80 -82.00-180.00   35
 11  \w     81.00 116.00   1.00    3.00    --   95.80 -82.00 -90.00   35
 12  \w     21.00  47.00   1.00    3.00    --   95.80 -82.00-150.00   26
 13  \w     93.00 124.00   1.00    3.00    --   95.80 -82.00-150.00   31
 14  \w     70.00  96.00   1.00    3.00    --   95.80 -30.00 -60.00   26
 15  \w     87.00 118.00   1.00    3.00    --   95.80 -82.00  30.00   31
 16  \w     76.00 180.00   1.00    3.00    --   95.80  15.00 -90.00  104
 17  \w      6.00  38.00   1.00    3.00    --   95.80 -30.00 -60.00   32
 18  \w     37.00  63.00   1.00    3.00    --   95.80 -82.00 -90.00   26
 19  \w     10.00 112.00   1.00    3.00    --   95.80 -30.00 150.00  102
 20  \w     16.00  80.00   1.00    3.00    --   95.80 -61.00 150.00   64
 21  \w     19.00 119.00   1.00    3.00    --   95.80 -61.00   0.00  100
;
_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      -0.1748475000
_diffrn_orient_matrix_UB_12      -0.0554834000
_diffrn_orient_matrix_UB_13      0.0082691000
_diffrn_orient_matrix_UB_21      -0.0499387000
_diffrn_orient_matrix_UB_22      0.0393413000
_diffrn_orient_matrix_UB_23      -0.0584703000
_diffrn_orient_matrix_UB_31      0.0328750000
_diffrn_orient_matrix_UB_32      -0.2352328000
_diffrn_orient_matrix_UB_33      -0.0117359000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0552
_diffrn_reflns_av_unetI/netI     0.0365
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       4
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_l_max       28
_diffrn_reflns_limit_l_min       -30
_diffrn_reflns_number            11187
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_theta_full        67.055
_diffrn_reflns_theta_max         67.055
_diffrn_reflns_theta_min         5.306
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_source_type              'Enhance (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    3.402
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.66747
_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 yellow'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.337
_exptl_crystal_description       block
_exptl_crystal_F_000             568
_exptl_crystal_size_max          0.36
_exptl_crystal_size_mid          0.27
_exptl_crystal_size_min          0.25
_refine_diff_density_max         0.224
_refine_diff_density_min         -0.239
_refine_diff_density_rms         0.037
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.043
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     163
_refine_ls_number_reflns         2408
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.043
_refine_ls_R_factor_all          0.0488
_refine_ls_R_factor_gt           0.0420
_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^)+(0.0500P)^2^+0.3970P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1073
_refine_ls_wR_factor_ref         0.1121
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2083
_reflns_number_total             2408
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c8qo00481a2.cif
_cod_data_source_block           exp_203
_cod_database_code               1554357
_shelx_shelxl_version_number     2016/6
_shelx_estimated_absorpt_t_max   0.483
_shelx_estimated_absorpt_t_min   0.374
_reflns_odcompleteness_completeness 99.85
_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:
 C1(H1A,H1B), C9(H9A,H9B)
2.b Aromatic/amide H refined with riding coordinates:
 C3(H3), C4(H4), C5(H5), C6(H6), C10(H10), C11(H11), C12(H12), C13(H13),
 C14(H14)
;
_shelx_res_checksum              86658
_shelx_hkl_checksum              59154
_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 2.838
_oxdiff_exptl_absorpt_empirical_full_min 0.437