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_7251065
_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
'C10 H8 Br2 I2 N2, 6(C6 H5 O3 S), 4(C5 H4 Br I N)'
_chemical_formula_sum            'C66 H54 Br6 I6 N6 O18 S6'
_chemical_formula_weight         2652.37
_space_group_crystal_system      orthorhombic
_space_group_IT_number           62
_space_group_name_Hall           '-P 2ac 2n'
_space_group_name_H-M_alt        'P n m a'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   dual
_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
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_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   16.0430(6)
_cell_length_b                   37.2257(16)
_cell_length_c                   6.8695(2)
_cell_measurement_reflns_used    12325
_cell_measurement_temperature    295
_cell_measurement_theta_max      32.4140
_cell_measurement_theta_min      3.0140
_cell_volume                     4102.5(3)
_computing_molecular_graphics    'Ortep for Windows (Farrugia, 2012)'
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_diffrn_detector_area_resol_mean 10.0000
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type  'XtaLAB Synergy, Dualflex, HyPix'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0835
_diffrn_reflns_av_unetI/netI     0.0473
_diffrn_reflns_Laue_measured_fraction_full 0.998
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_diffrn_reflns_limit_k_max       47
_diffrn_reflns_limit_k_min       -47
_diffrn_reflns_limit_l_max       8
_diffrn_reflns_limit_l_min       -8
_diffrn_reflns_number            32732
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.000
_diffrn_reflns_theta_min         3.015
_diffrn_source                   'micro-focus sealed X-ray tube'
_exptl_absorpt_coefficient_mu    5.415
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.26791
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.41.92a (Rigaku Oxford Diffraction, 2020)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    2.147
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             2520
_exptl_crystal_size_max          0.56
_exptl_crystal_size_mid          0.37
_exptl_crystal_size_min          0.10
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_refine_ls_number_reflns         4545
_refine_ls_number_restraints     26
_refine_ls_restrained_S_all      1.270
_refine_ls_R_factor_all          0.0967
_refine_ls_R_factor_gt           0.0729
_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^)+(0.0201P)^2^+36.5582P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1259
_refine_ls_wR_factor_ref         0.1327
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3593
_reflns_number_total             4545
_reflns_threshold_expression     'I > 2\s(I)'
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_cod_depositor_comments
'Adding full bibliography for 7251062--7251071.cif.'
_cod_database_code               7251065
_shelx_shelxl_version_number     2019/3
_shelx_res_checksum              80601