A 1:1:1 co-crystal solvate comprising 2,2'-dithiodibenzoic acid, 2-chlorobenzoic acid and <i>N</i>,<i>N</i>-dimethylformamide: crystal structure, Hirshfeld surface analysis and computational study
Tan, Sang Loon; Tiekink, Edward R. T.; Acta Crystallographica Section E 75 (2019) 475–481; doi:10.1107/S205698901900375X

data_2242879
_publ_section_title
;
 A 1:1:1 co-crystal solvate comprising 2,2'-dithiodibenzoic acid,
 2-chlorobenzoic acid and <i>N</i>,<i>N</i>-dimethylformamide: crystal
 structure, Hirshfeld surface analysis and computational study
;
_journal_coeditor_code           HB7808
_journal_issue                   4
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              475
_journal_page_last               481
_journal_paper_doi               10.1107/S205698901900375X
_journal_volume                  75
_journal_year                    2019
_chemical_formula_iupac          'C14 H10 O4 S2, C7 H5 Cl O2, C3 H7 N O'
_chemical_formula_moiety         'C14 H10 O4 S2, C7 H5 Cl O2, C3 H7 N O'
_chemical_formula_sum            'C24 H22 Cl N O7 S2'
_chemical_formula_weight         536.00
_chemical_name_systematic
'2,2'-Dithiodibenzoic acid--2-chlorobenzoic acid--<i>N</i>,<i>N</i>-dimethylformamide (1/1/1)'
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     dual
_audit_creation_method
;
Olex2 1.2-ac3
(compiled 2017.08.10 svn.r3458 for OlexSys, GUI svn.r5381)
;
_cell_angle_alpha                86.136(3)
_cell_angle_beta                 88.693(2)
_cell_angle_gamma                65.080(4)
_cell_formula_units_Z            2
_cell_length_a                   7.7487(3)
_cell_length_b                   7.8575(3)
_cell_length_c                   21.4486(6)
_cell_measurement_reflns_used    21119
_cell_measurement_temperature    99.97(15)
_cell_measurement_theta_max      76.0820
_cell_measurement_theta_min      4.0420
_cell_volume                     1181.61(8)
_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), <i>OLEX2</i> (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      99.97(15)
_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  0.0569
_diffrn_reflns_av_unetI/netI     0.0235
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       26
_diffrn_reflns_limit_l_min       -24
_diffrn_reflns_number            40239
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         76.106
_diffrn_reflns_theta_min         4.132
_diffrn_source                   'micro-focus sealed X-ray tube'
_exptl_absorpt_coefficient_mu    3.496
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.413
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details
;
(CrysAlisPro; Rigaku OD, 2018)
;
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.506
_exptl_crystal_description       plate
_exptl_crystal_F_000             556
_exptl_crystal_size_max          0.193
_exptl_crystal_size_mid          0.117
_exptl_crystal_size_min          0.025
_refine_diff_density_max         1.213
_refine_diff_density_min         -0.834
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.097
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     330
_refine_ls_number_reflns         4915
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.097
_refine_ls_R_factor_all          0.0704
_refine_ls_R_factor_gt           0.0667
_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^)+(0.1187P)^2^+2.0348P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1990
_refine_ls_wR_factor_ref         0.2025
_reflns_number_gt                4507
_reflns_number_total             4915
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            hb7808sup1.cif
_cod_data_source_block           I
_cod_database_code               2242879
_cod_database_fobs_code          2242879
_shelx_hkl_checksum              5851
_shelx_res_checksum              16345