Halopyridinium cations as bifunctional donors of halogen and hydrogen bonds in salts with benzenesulfonic and p-toluenesulfonic acids
Čulig, Matija; Nemec, Vinko; Bregović, Nikola; Cinčić, Dominik; CrystEngComm 27 (2025) 7638–7643; doi:10.1039/D5CE00870K

data_7251070
_publ_section_title
;
 Halopyridinium cations as bifunctional donors of halogen and hydrogen
 bonds in salts with benzenesulfonic and p-toluenesulfonic acids
;
_journal_issue                   47
_journal_name_full               CrystEngComm
_journal_page_first              7638
_journal_page_last               7643
_journal_paper_doi               10.1039/D5CE00870K
_journal_volume                  27
_journal_year                    2025
_chemical_formula_moiety         'C7 H7 O3 S, C5 H5 Br N'
_chemical_formula_sum            'C12 H12 Br N O3 S'
_chemical_formula_weight         330.20
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2yn'
_space_group_name_H-M_alt        'P 1 21/n 1'
_atom_sites_solution_hydrogens   geom
_audit_creation_method           SHELXL-2019/3
_audit_update_record
;
2025-09-02 deposited with the CCDC.	2025-10-23 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 111.921(14)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   7.5180(10)
_cell_length_b                   19.441(3)
_cell_length_c                   9.7450(12)
_cell_measurement_reflns_used    1358
_cell_measurement_temperature    295
_cell_measurement_theta_max      24.3860
_cell_measurement_theta_min      4.4050
_cell_volume                     1321.3(3)
_computing_structure_refinement  'SHELXL-2019/2 (Sheldrick, 2019)'
_diffrn_ambient_temperature      295
_diffrn_detector_area_resol_mean 16.3426
_diffrn_measured_fraction_theta_full 0.995
_diffrn_measured_fraction_theta_max 0.994
_diffrn_measurement_device_type  'Xcalibur, Sapphire3'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0595
_diffrn_reflns_av_unetI/netI     0.0751
_diffrn_reflns_Laue_measured_fraction_full 0.995
_diffrn_reflns_Laue_measured_fraction_max 0.994
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       24
_diffrn_reflns_limit_k_min       -20
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            8423
_diffrn_reflns_point_group_measured_fraction_full 0.995
_diffrn_reflns_point_group_measured_fraction_max 0.994
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.995
_diffrn_reflns_theta_min         4.193
_diffrn_source                   'fine-focus sealed X-ray tube'
_exptl_absorpt_coefficient_mu    3.268
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.47468
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.41.95a (Rigaku Oxford Diffraction, 2021)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.660
_exptl_crystal_description       plate
_exptl_crystal_F_000             664
_exptl_crystal_size_max          0.60
_exptl_crystal_size_mid          0.34
_exptl_crystal_size_min          0.12
_refine_diff_density_max         0.301
_refine_diff_density_min         -0.429
_refine_diff_density_rms         0.096
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.994
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     164
_refine_ls_number_reflns         2872
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.994
_refine_ls_R_factor_all          0.1162
_refine_ls_R_factor_gt           0.0480
_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^)+(0.0314P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0827
_refine_ls_wR_factor_ref         0.1065
_reflns_Friedel_coverage         0.000
_reflns_number_gt                1529
_reflns_number_total             2872
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d5ce00870k2.cif
_cod_data_source_block           ptsa_3BrpyH
_cod_depositor_comments
'Adding full bibliography for 7251062--7251071.cif.'
_cod_original_sg_symbol_H-M      'P 21/n'
_cod_database_code               7251070
_shelx_shelxl_version_number     2019/3
_shelx_res_checksum              32246