Two stacking types of three-dimensional cocrystal structures based on multiple hydrogen bonds
Yan, Wenjin; Wang, Tianwei; Hu, Yingxin; Chen, Longming; Wang, Peng; Pang, Chaoran; Lu, Rongwen; Zhang, Shufen; CrystEngComm 27 (2025) 269–276; doi:10.1039/D4CE01071J

data_7249663
_publ_section_title
;
 Two stacking types of three-dimensional cocrystal structures based on
 multiple hydrogen bonds
;
_journal_issue                   2
_journal_name_full               CrystEngComm
_journal_page_first              269
_journal_page_last               276
_journal_paper_doi               10.1039/D4CE01071J
_journal_volume                  27
_journal_year                    2025
_chemical_formula_moiety         '2(C3 H3 N3 S3), 2(C6 H12 N4)'
_chemical_formula_sum            'C18 H30 N14 S6'
_chemical_formula_weight         634.92
_chemical_name_common            Phpm
_chemical_name_systematic        TAC-HMTA
_space_group_crystal_system      hexagonal
_space_group_IT_number           186
_space_group_name_Hall           'P 6c -2c'
_space_group_name_H-M_alt        'P 63 m c'
_atom_sites_solution_hydrogens   geom
_audit_creation_date             2024-04-15
_audit_creation_method
;
Olex2 1.5
(compiled 2024.02.16 svn.r378c4104 for OlexSys, GUI svn.r6928)
;
_audit_update_record
;
2024-07-08 deposited with the CCDC.	2024-12-02 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                120
_cell_formula_units_Z            2
_cell_length_a                   9.6534(18)
_cell_length_b                   9.6534(18)
_cell_length_c                   16.438(5)
_cell_measurement_reflns_used    3621
_cell_measurement_temperature    120.15
_cell_measurement_theta_max      24.768
_cell_measurement_theta_min      2.436
_cell_volume                     1326.6(5)
_computing_cell_refinement       'SAINT V8.40A (Bruker, 2019)'
_computing_data_reduction        'SAINT V8.40A (Bruker, 2019)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2019/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_diffrn_ambient_temperature      298.15
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0920
_diffrn_reflns_av_unetI/netI     0.0588
_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       -10
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            8697
_diffrn_reflns_point_group_measured_fraction_full 0.991
_diffrn_reflns_point_group_measured_fraction_max 0.991
_diffrn_reflns_theta_full        25.065
_diffrn_reflns_theta_max         25.065
_diffrn_reflns_theta_min         2.436
_diffrn_source_current           1.4
_diffrn_source_power             0.07
_diffrn_source_voltage           50.0
_exptl_absorpt_coefficient_mu    0.557
_exptl_absorpt_correction_T_max  0.7452
_exptl_absorpt_correction_T_min  0.5957
_exptl_absorpt_correction_type   none
_exptl_absorpt_process_details
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.1475 before and 0.0885 after correction.
The Ratio of minimum to maximum transmission is 0.7994.
The \l/2 correction factor is Not present.
;
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.589
_exptl_crystal_description       block
_exptl_crystal_F_000             664
_refine_diff_density_max         0.745
_refine_diff_density_min         -0.349
_refine_diff_density_rms         0.078
_refine_ls_abs_structure_details
;
 Refined as an inversion twin.
;
_refine_ls_abs_structure_Flack   0.0(4)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.057
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     74
_refine_ls_number_reflns         931
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.056
_refine_ls_R_factor_all          0.0598
_refine_ls_R_factor_gt           0.0455
_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^)+(0.0606P)^2^+1.3654P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1058
_refine_ls_wR_factor_ref         0.1140
_reflns_Friedel_coverage         0.912
_reflns_Friedel_fraction_full    0.984
_reflns_Friedel_fraction_max     0.984
_reflns_number_gt                773
_reflns_number_total             931
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d4ce01071j2.cif
_cod_data_source_block           4_pl
_cod_depositor_comments          'Adding full bibliography for 7249663.cif.'
_cod_original_cell_volume        1326.6(6)
_cod_database_code               7249663
_shelx_shelxl_version_number     2019/3
_olex2_refinement_description
;
1. Twinned data refinement
 Scales: 1.0(4)
 -0.0(4)
2. Fixed Uiso
 At 1.2 times of:
  All C(H,H) groups, All N(H) groups
3. Others
 Fixed Sof: H4A(0.5) H4B(0.5) H5A(0.5) H5B(0.5)
4.a Secondary CH2 refined with riding coordinates:
 C3(H3A,H3B), C4(H4A,H4B), C5(H5A,H5B), C6(H6A,H6B)
4.b Aromatic/amide H refined with riding coordinates:
 N1(H1), N2(H2)
;
_shelx_res_checksum              59059
_shelx_hkl_checksum              82509
_olex2_submission_special_instructions 'No special instructions were received'