A 1:2 co-crystal of 2,2′-dithiodibenzoic acid and benzoic acid: crystal structure, Hirshfeld surface analysis and computational study
Tan, Sang Loon; Tiekink, Edward R. T.; Acta Crystallographica Section E Crystallographic Communications 75 (2019) 1–; doi:10.1107/S2056989018017097

data_2021414
_publ_section_title
;
 A 1:2 co-crystal of 2,2&#x2032;-dithiodibenzoic acid and benzoic acid:
 crystal structure, Hirshfeld surface analysis and computational study
;
_journal_coeditor_code           HB7790
_journal_issue                   1
_journal_name_full
'Acta Crystallographica Section E Crystallographic Communications'
_journal_page_first              1
_journal_paper_doi               10.1107/S2056989018017097
_journal_volume                  75
_journal_year                    2019
_chemical_formula_iupac          'C14 H10 O4 S2, 2C7 H6 O2'
_chemical_formula_moiety         'C14 H10 O4 S2, 2(C7 H6 O2)'
_chemical_formula_sum            'C28 H22 O8 S2'
_chemical_formula_weight         550.58
_chemical_name_systematic
;
2,2'-Dithiodibenzoic acid--benzoic acid (1/2)
;
_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'
_symmetry_space_group_name_Hall  '-C 2yc'
_symmetry_space_group_name_H-M   'C 1 2/c 1'
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     dual
_cell_angle_alpha                90
_cell_angle_beta                 95.864(2)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   8.23110(10)
_cell_length_b                   13.3220(2)
_cell_length_c                   22.7038(3)
_cell_measurement_reflns_used    18092
_cell_measurement_temperature    100.00(10)
_cell_measurement_theta_max      76.1700
_cell_measurement_theta_min      3.8970
_cell_volume                     2476.55(6)
_computing_cell_refinement
;
CrysAlis PRO (Rigaku OD, 2018)
;
_computing_data_collection
;
CrysAlis PRO (Rigaku OD, 2018)
;
_computing_data_reduction
;
CrysAlis PRO (Rigaku OD, 2018)
;
_computing_molecular_graphics
;
ORTEP-3 for Windows (Farrugia, 2012), OLEX2 (Dolomanov <i>et al.</i>,
2009)
and Mercury (Macrae <i>et al.</i>, 2006)
;
_computing_publication_material
;
publCIF (Westrip, 2010)
;
_computing_structure_refinement
;
SHELXL (Sheldrick, 2015<i>a</i>)
;
_computing_structure_solution
;
SHELXT (Sheldrick, 2015<i>b</i>)
;
_diffrn_ambient_temperature      100.00(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 5.2558
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB Synergy, Dualflex, AtlasS2'
_diffrn_measurement_method       '\w scans'
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0390
_diffrn_reflns_av_unetI/netI     0.0132
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       28
_diffrn_reflns_limit_l_min       -28
_diffrn_reflns_number            32177
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         76.190
_diffrn_reflns_theta_min         3.915
_diffrn_source                   'micro-focus sealed X-ray tube'
_exptl_absorpt_coefficient_mu    2.407
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.643
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details
;
(CrysAlis PRO; Rigaku OD, 2018)
;
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.477
_exptl_crystal_description       prism
_exptl_crystal_F_000             1144
_exptl_crystal_size_max          0.198
_exptl_crystal_size_mid          0.112
_exptl_crystal_size_min          0.062
_refine_diff_density_max         0.663
_refine_diff_density_min         -0.490
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.082
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     180
_refine_ls_number_reflns         2589
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.082
_refine_ls_R_factor_all          0.0401
_refine_ls_R_factor_gt           0.0392
_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^)+(0.0597P)^2^+4.0853P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1082
_refine_ls_wR_factor_ref         0.1091
_reflns_number_gt                2511
_reflns_number_total             2589
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            hb7790sup1.cif
_cod_data_source_block           I
_cod_database_code               2021414
_cod_database_fobs_code          2021414
_shelx_hkl_checksum              44094
_shelx_res_checksum              69765