The N–H⋯S hydrogen bonding pattern in trithiocyanuric acid in crystalline state: geometric, topological, and energetic analysis of trithiocyanuric acid cocrystals
Wzgarda-Raj, Kinga; Rybarczyk-Pirek, Agnieszka J.; Palusiak, Marcin; CrystEngComm 27 (2025) 784–794; doi:10.1039/D4CE01153H

data_7249783
_publ_section_title
;
 The N--H&#x22EF;S hydrogen bonding pattern in trithiocyanuric acid in
 crystalline state: geometric, topological, and energetic analysis of
 trithiocyanuric acid cocrystals
;
_journal_issue                   6
_journal_name_full               CrystEngComm
_journal_page_first              784
_journal_page_last               794
_journal_paper_doi               10.1039/D4CE01153H
_journal_volume                  27
_journal_year                    2025
_chemical_formula_moiety         'C8 H6 N4 S2, 2(C3 H3 N3 S3)'
_chemical_formula_sum            'C14 H12 N10 S8'
_chemical_formula_weight         576.82
_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   mixed
_atom_sites_solution_primary     dual
_audit_creation_date             2024-01-23
_audit_creation_method
;
Olex2 1.5
(compiled 2023.08.24 svn.re1ec1418 for OlexSys, GUI svn.r6817)
;
_audit_update_record
;
2024-07-13 deposited with the CCDC.	2024-12-27 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 111.7533(8)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   19.96872(14)
_cell_length_b                   5.45162(3)
_cell_length_c                   23.70011(17)
_cell_measurement_reflns_used    24710
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      76.3070
_cell_measurement_theta_min      3.9930
_cell_volume                     2396.31(3)
_computing_cell_refinement       'CrysAlisPro 1.171.40.78a (Rigaku OD, 2020)'
_computing_data_collection       'CrysAlisPro 1.171.40.78a (Rigaku OD, 2020)'
_computing_data_reduction        'CrysAlisPro 1.171.40.78a (Rigaku OD, 2020)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_diffrn_ambient_environment      air
_diffrn_ambient_temperature      293(1)
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            HyPix
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.991
_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    -12.00  28.00   0.50    2.00    --  -47.45  19.00  30.00   80
  2  \w    -49.00 -14.00   0.50    6.80    --  -86.25  45.00 -60.00   70
  3  \w    -49.00 -14.00   0.50    6.80    --  -86.25  45.00 -90.00   70
  4  \w    -75.00 -13.00   0.50    6.80    --  -86.25  61.00 -60.00  124
  5  \w    -77.00  25.00   0.50    2.00    --  -47.45  92.00 102.00  204
  6  \w    -19.00  77.00   0.50    2.00    --   47.45 -92.00 -10.00  192
  7  \w     33.00 106.00   0.50    6.80    --  105.86 -92.00 -10.00  146
  8  \w     39.00 118.00   0.50    6.80    --  105.86-133.00-125.28  158
  9  \w     33.00 105.00   0.50    6.80    --  105.86 -95.00-120.00  144
 10  \w     34.00 112.00   0.50    6.80    --  105.86-125.00-150.00  156
 11  \w     33.00 105.00   0.50    6.80    --  105.86 -95.00-180.00  144
 12  \w     33.00 105.00   0.50    6.80    --  105.86 -95.00-150.00  144
 13  \w     33.00  75.00   0.50    6.80    --  105.86 -61.00   0.00   84
 14  \w     33.00 105.00   0.50    6.80    --  105.86 -95.00 -30.00  144
 15  \w     33.00 105.00   0.50    6.80    --  105.86 -95.00  90.00  144
 16  \w     38.00 116.00   0.50    6.80    --  105.86-131.00 150.88  156
 17  \w     33.00 105.00   0.50    6.80    --  105.86 -95.00 120.00  144
 18  \w     92.00 176.00   0.50    6.80    --  105.86  15.00  60.00  168
 19  \w     93.00 178.00   0.50    6.80    --  105.86  30.00 150.00  170
 20  \w     95.00 178.00   0.50    6.80    --  105.86 125.00  60.00  166
 21  \w    102.00 178.00   0.50    6.80    --  105.86  92.00 102.00  152
 22  \w     92.00 176.00   0.50    6.80    --  105.86  15.00   0.00  168
 23  \w     93.00 178.00   0.50    6.80    --  105.86  30.00-120.00  170
 24  \w     33.00 105.00   0.50    6.80    --  105.86 -95.00 -60.00  144
 25  \w     33.00  75.00   0.50    6.80    --  105.86 -61.00 150.00   84
 26  \w    -27.00  12.00   0.50    2.00    --   47.45 -19.00  90.00   78
 27  \w    -27.00  12.00   0.50    2.00    --   47.45 -19.00 120.00   78
 28  \w    -24.00  62.00   0.50    2.00    --   47.45 -57.00   0.00  172
 29  \w    -27.00  12.00   0.50    2.00    --   47.45 -19.00 -90.00   78
 30  \w     25.00 120.00   0.50    2.00    --   47.45  77.00  30.00  190
 31  \w     25.00 120.00   0.50    2.00    --   47.45  77.00-120.00  190
 32  \w     25.00 120.00   0.50    2.00    --   47.45  77.00 -60.00  190
 33  \w     25.00 120.00   0.50    2.00    --   47.45  77.00  90.00  190
 34  \w     25.00 120.00   0.50    2.00    --   47.45  77.00 -30.00  190
 35  \w     25.00 120.00   0.50    2.00    --   47.45  77.00-180.00  190
 36  \w     25.00 120.00   0.50    2.00    --   47.45  77.00 150.00  190
 37  \w    -80.00 -13.00   0.50    6.80    --  -86.25  92.00 102.00  134
 38  \w    -86.00 -13.00   0.50    6.80    --  -86.25 125.00 -30.00  146
 39  \w   -120.00 -32.00   0.50    2.00    --  -47.45 -58.00  76.13  176
 40  \w   -120.00 -73.00   0.50    2.00    --  -47.45-125.00 120.00   94
 41  \w   -159.00 -80.00   0.50    6.80    --  -86.25 -92.00 -10.00  158
 42  \w   -159.00 -65.00   0.50    6.80    --  -86.25 -72.00  61.10  188
 43  \w   -159.00 -63.00   0.50    6.80    --  -86.25 -77.00  23.47  192
 44  \w   -159.00 -70.00   0.50    6.80    --  -86.25 -61.00-180.00  178
 45  \w   -159.00 -63.00   0.50    6.80    --  -86.25 -77.00 -30.00  192
 46  \w   -159.00 -62.00   0.50    6.80    --  -86.25 -80.00-122.96  194
 47  \w   -159.00 -64.00   0.50    6.80    --  -86.25 -75.00 -72.00  190
 48  \w   -159.00 -63.00   0.50    6.80    --  -86.25 -77.00 120.00  192
 49  \w   -159.00 -63.00   0.50    6.80    --  -86.25 -77.00 150.00  192
 50  \w   -159.00 -63.00   0.50    6.80    --  -86.25 -77.00  90.00  192
 51  \w   -159.00 -63.00   0.50    6.80    --  -86.25 -77.00 -90.00  192
 52  \w   -159.00 -64.00   0.50    6.80    --  -86.25 -76.00-176.76  190
 53  \w   -159.00 -63.00   0.50    6.80    --  -86.25 -78.00   6.82  192
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB Synergy, Dualflex, HyPix'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0220541000
_diffrn_orient_matrix_UB_12      0.1620646000
_diffrn_orient_matrix_UB_13      -0.0434874000
_diffrn_orient_matrix_UB_21      -0.0775319000
_diffrn_orient_matrix_UB_22      -0.0138078000
_diffrn_orient_matrix_UB_23      -0.0473327000
_diffrn_orient_matrix_UB_31      -0.0200936000
_diffrn_orient_matrix_UB_32      0.2310873000
_diffrn_orient_matrix_UB_33      0.0276663000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0279
_diffrn_reflns_av_unetI/netI     0.0103
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.991
_diffrn_reflns_limit_h_max       24
_diffrn_reflns_limit_h_min       -23
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_l_max       29
_diffrn_reflns_limit_l_min       -29
_diffrn_reflns_number            34136
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.991
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         76.539
_diffrn_reflns_theta_min         4.017
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'PhotonJet (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    7.137
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.910
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.40.78a (Rigaku Oxford Diffraction, 2020)
Numerical absorption correction based on gaussian integration over
			a multifaceted crystal model
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.599
_exptl_crystal_description       plate
_exptl_crystal_F_000             1176
_exptl_crystal_size_max          0.110
_exptl_crystal_size_mid          0.044
_exptl_crystal_size_min          0.019
_refine_diff_density_max         0.271
_refine_diff_density_min         -0.247
_refine_diff_density_rms         0.036
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.071
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     157
_refine_ls_number_reflns         2490
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.071
_refine_ls_R_factor_all          0.0238
_refine_ls_R_factor_gt           0.0226
_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^)+(0.0315P)^2^+1.3515P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0620
_refine_ls_wR_factor_ref         0.0628
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2384
_reflns_number_total             2490
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d4ce01153h2.cif
_cod_data_source_block           exp_19
_cod_depositor_comments
'Adding full bibliography for 7249780--7249783.cif.'
_cod_database_code               7249783
_shelx_shelxl_version_number     2018/3
_chemical_oxdiff_formula         'C11 H10 N O'
_reflns_odcompleteness_completeness 99.96
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
2. Rigid bond restraints
 S2, S4
 with sigma for 1-2 distances of 0.1 and sigma for 1-3 distances of 0.1
3. Uiso/Uaniso restraints and constraints
S2 \\sim S4: within 2A with sigma of 0.01 and sigma for terminal atoms of 0.02
within 2A
4.a Aromatic/amide H refined with riding coordinates:
 C12(H12), C16(H16), C15(H15)
;
_shelx_res_checksum              40097
_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 1.424
_oxdiff_exptl_absorpt_empirical_full_min 0.872