A catalyst-free method for the synthesis of 1,4,2-dithiazoles from isothiocyanates and hydroxylamine triflic acid salts.
An, Zhenyu; Wang, Ting; Liu, Yafeng; Ren, Yi; Yan, Rulong; Organic & biomolecular chemistry 19 (2021) 6206–6209; doi:10.1039/d1ob00938a

data_7158149
_publ_section_title
;
 A catalyst-free method for the synthesis of 1,4,2-dithiazoles from
 isothiocyanates and hydroxylamine triflic acid salts.
;
_journal_issue                   28
_journal_name_full               'Organic &amp; biomolecular chemistry'
_journal_page_first              6206
_journal_page_last               6209
_journal_paper_doi               10.1039/d1ob00938a
_journal_volume                  19
_journal_year                    2021
_chemical_formula_moiety         'C14 H11 N3 S2'
_chemical_formula_sum            'C14 H11 N3 S2'
_chemical_formula_weight         285.37
_space_group_crystal_system      monoclinic
_space_group_IT_number           15
_space_group_name_Hall           '-C 2yc'
_space_group_name_H-M_alt        'C 1 2/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_audit_creation_date             2019-12-20
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_audit_update_record
;
2020-09-15 deposited with the CCDC.	2021-06-24 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 99.6071(19)
_cell_angle_gamma                90
_cell_formula_units_Z            16
_cell_length_a                   16.8782(3)
_cell_length_b                   17.0499(3)
_cell_length_c                   19.0329(4)
_cell_measurement_reflns_used    5001
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      69.5940
_cell_measurement_theta_min      4.1260
_cell_volume                     5400.31(18)
_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    'ShelXS (Sheldrick, 2008)'
_diffrn_ambient_temperature      293(2)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 16.0733
_diffrn_detector_type            Eos
_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     35.00 102.00   1.00    3.00    --   54.00  57.00 -60.00   67
  2  \w     95.00 174.00   1.00    4.00    --  108.00  63.00  30.00   79
  3  \w    113.00 177.00   1.00    4.00    --  108.00 111.00   0.00   64
  4  \w    140.00 166.00   1.00    4.00    --  108.00  38.00-120.00   26
  5  \w    101.00 175.00   1.00    4.00    --  108.00 111.00 -30.00   74
  6  \w     83.00 175.00   1.00    4.00    --  108.00  77.00 150.00   92
  7  \w     38.00 119.00   1.00    3.00    --   54.00  57.00 150.00   81
  8  \w     34.00  80.00   1.00    3.00    --   54.00 -38.00   0.00   46
  9  \w     54.00 116.00   1.00    4.00    --  108.00-111.00  60.00   62
 10  \w     42.00 120.00   1.00    4.00    --  108.00 -77.00  60.00   78
 11  \w     65.00 118.00   1.00    4.00    --  108.00 -63.00-150.00   53
 12  \w     37.00  63.00   1.00    3.00    --   54.00-125.00-180.00   26
 13  \w      6.00  95.00   1.00    3.00    --   54.00 -99.00   0.00   89
 14  \w    -20.00  58.00   1.00    1.50    --    0.00  57.00  90.00   78
 15  \w    -71.00 -20.00   1.00    1.50    --    0.00 -19.00 150.00   51
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, Eos'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0297618000
_diffrn_orient_matrix_UB_12      -0.0080311000
_diffrn_orient_matrix_UB_13      -0.0719410000
_diffrn_orient_matrix_UB_21      -0.0217555000
_diffrn_orient_matrix_UB_22      -0.0878076000
_diffrn_orient_matrix_UB_23      -0.0023818000
_diffrn_orient_matrix_UB_31      -0.0848855000
_diffrn_orient_matrix_UB_32      0.0196398000
_diffrn_orient_matrix_UB_33      -0.0395717000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0199
_diffrn_reflns_av_unetI/netI     0.0245
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       19
_diffrn_reflns_limit_h_min       -20
_diffrn_reflns_limit_k_max       20
_diffrn_reflns_limit_k_min       -20
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_number            10491
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_theta_full        66.599
_diffrn_reflns_theta_max         66.599
_diffrn_reflns_theta_min         3.712
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    3.474
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.50920
_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            'clear light colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.404
_exptl_crystal_description       block
_exptl_crystal_F_000             2368
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.16
_exptl_crystal_size_min          0.12
_refine_diff_density_max         0.256
_refine_diff_density_min         -0.259
_refine_diff_density_rms         0.036
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.052
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     343
_refine_ls_number_reflns         4766
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.052
_refine_ls_R_factor_all          0.0459
_refine_ls_R_factor_gt           0.0376
_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^)+(0.0482P)^2^+2.3825P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0978
_refine_ls_wR_factor_ref         0.1059
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3994
_reflns_number_total             4766
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d1ob00938a2.cif
_cod_data_source_block           wangt_1218
_cod_depositor_comments
;
        Adding full bibliography for 7158149.cif.

2024-10-30
Z value and formula fixed to values more according to usual
chemical conventions.                 miguel
;
_cod_original_formula_sum            'C28 H22 N6 S4'
_cod_original_formula_weight         570.75
_cod_original_formula_moiety         '2(C14 H11 N3 S2)'
_cod_original_formula_units_Z            8
_cod_original_cell_volume        5400.32(18)
_cod_database_code               7158149
_shelx_shelxl_version_number     2018/3
_shelx_estimated_absorpt_t_max   0.681
_shelx_estimated_absorpt_t_min   0.543
_reflns_odcompleteness_completeness 99.92
_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 N(H) groups
2.a Aromatic/amide H refined with riding coordinates:
 N7(H7), C18(H18), C21(H21), C22(H22), C24(H24), C26(H26), C27(H27), C29(H29),
 C31(H31), C32(H32), C33(H33), N14(H14), C15(H15), C16(H16), C17(H17), C19(H19),
  C20(H20), C23(H23), C25(H25), C28(H28), C30(H30), C34(H34)
;
_shelx_res_checksum              66779
_shelx_hkl_checksum              38330
_olex2_date_sample_data_collection 2019-12-19
_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 1.673
_oxdiff_exptl_absorpt_empirical_full_min 0.594