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_7249782
_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         'C3 H3 N3 S3, C4 H4 N2 O'
_chemical_formula_sum            'C7 H7 N5 O S3'
_chemical_formula_weight         273.36
_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   mixed
_atom_sites_solution_primary     dual
_audit_creation_date             2024-07-13
_audit_creation_method
;
Olex2 1.5
(compiled 2024.02.16 svn.r378c4104 for OlexSys, GUI svn.r6928)
;
_audit_update_record
;
2024-07-13 deposited with the CCDC.	2024-12-27 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 96.579(2)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   4.49550(10)
_cell_length_b                   16.5288(3)
_cell_length_c                   14.9573(3)
_cell_measurement_reflns_used    14763
_cell_measurement_temperature    149.99(10)
_cell_measurement_theta_max      30.9710
_cell_measurement_theta_min      2.4580
_cell_volume                     1104.09(4)
_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      N~2~
_diffrn_ambient_temperature      149.99(10)
_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 0.872
_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    -29.00  26.00   0.50   16.69    --   -5.34 -96.00 -33.00  110
  2  \w    -29.00  37.00   0.50   16.69    --    5.49 -96.00 -33.00  132
  3  \w    -23.00  28.00   0.50   16.69    --   -5.34 -99.00-120.00  102
  4  \w    -23.00  39.00   0.50   16.69    --    5.49 -99.00-150.00  124
  5  \w    -67.00  21.00   0.50   16.69    --    5.49 -57.00 -30.00  176
  6  \w    -23.00  27.00   0.50   16.69    --    5.49 -99.00  60.00  100
  7  \w    -23.00  39.00   0.50   16.69    --    5.49 -99.00 150.00  124
  8  \w    -81.00  -9.00   0.50   16.69    --   -5.34 -19.00 150.00  144
  9  \w    -17.00  78.00   0.50   16.69    --    5.49  77.00   0.00  190
 10  \w    -70.00  -9.00   0.50   16.69    --    5.49 -19.00-120.00  122
;
_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      0.0359591000
_diffrn_orient_matrix_UB_12      0.0373472000
_diffrn_orient_matrix_UB_13      -0.0195087000
_diffrn_orient_matrix_UB_21      0.0582374000
_diffrn_orient_matrix_UB_22      0.0145831000
_diffrn_orient_matrix_UB_23      0.0430774000
_diffrn_orient_matrix_UB_31      0.1433029000
_diffrn_orient_matrix_UB_32      -0.0153060000
_diffrn_orient_matrix_UB_33      -0.0065398000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0337
_diffrn_reflns_av_unetI/netI     0.0199
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.872
_diffrn_reflns_limit_h_max       5
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_k_max       21
_diffrn_reflns_limit_k_min       -23
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            25107
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.872
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         31.065
_diffrn_reflns_theta_min         2.464
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'PhotonJet (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    0.656
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.639
_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            yellow
_exptl_crystal_density_diffrn    1.645
_exptl_crystal_description       block
_exptl_crystal_F_000             560
_exptl_crystal_size_max          0.259
_exptl_crystal_size_mid          0.06
_exptl_crystal_size_min          0.045
_refine_diff_density_max         0.338
_refine_diff_density_min         -0.249
_refine_diff_density_rms         0.052
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.108
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     166
_refine_ls_number_reflns         3086
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.108
_refine_ls_R_factor_all          0.0313
_refine_ls_R_factor_gt           0.0254
_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^)+(0.0287P)^2^+0.3155P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0629
_refine_ls_wR_factor_ref         0.0646
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2680
_reflns_number_total             3086
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d4ce01153h2.cif
_cod_data_source_block           exp_69
_cod_depositor_comments
'Adding full bibliography for 7249780--7249783.cif.'
_cod_database_code               7249782
_shelx_shelxl_version_number     2018/3
_chemical_oxdiff_formula         'C11 H10 N O'
_reflns_odcompleteness_completeness 99.87
_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. Others
 Fixed Sof: S4(0.5) S1(0.5)
3.a Aromatic/amide H refined with riding coordinates:
 C16(H16), C15(H15), C12(H12), C13(H13)
;
_shelx_res_checksum              68735
_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 1.181
_oxdiff_exptl_absorpt_empirical_full_min 0.913