A 1:2 co-crystal of 2,2'-thiodibenzoic acid and triphenylphosphane oxide: crystal structure, Hirshfeld surface analysis and computational study
Tan, Sang Loon; Tiekink, Edward R. T.; Acta Crystallographica Section E 74 (2018) 1764–1771; doi:10.1107/S205698901801544X

data_2242725
_publ_section_title
;
 A 1:2 co-crystal of 2,2'-thiodibenzoic acid and triphenylphosphane oxide:
 crystal structure, Hirshfeld surface analysis and computational study
;
_journal_coeditor_code           HB7782
_journal_issue                   12
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              1764
_journal_page_last               1771
_journal_paper_doi               10.1107/S205698901801544X
_journal_volume                  74
_journal_year                    2018
_chemical_formula_iupac          '2C18 H15 O P, C14 H10 O4 S'
_chemical_formula_moiety         '2(C18 H15 O P), C14 H10 O4 S'
_chemical_formula_sum            'C50 H40 O6 P2 S'
_chemical_formula_weight         830.82
_chemical_name_common
;
2,2'-Thiodibenzoic acid--triphenylphosphane oxide (1/2)
;
_chemical_name_systematic
;
2-[(2-Carboxyphenyl)sulfanyl]benzoic acid--(diphenylphosphoryl)benzene (1/2)
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2ybc'
_space_group_name_H-M_alt        'P 1 21/c 1'
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 1 21/c 1'
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     dual
_cell_angle_alpha                90
_cell_angle_beta                 101.4900(10)
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   10.70850(10)
_cell_length_b                   41.9751(2)
_cell_length_c                   18.92680(10)
_cell_measurement_reflns_used    52739
_cell_measurement_temperature    100
_cell_measurement_theta_max      75.9320
_cell_measurement_theta_min      4.1620
_cell_volume                     8336.92(10)
_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>b</i>)
;
_computing_structure_solution
;
SHELXT (Sheldrick, 2015<i>a</i>)
;
_diffrn_ambient_temperature      100
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 5.2558
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.975
_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  0.0246
_diffrn_reflns_av_unetI/netI     0.0141
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       52
_diffrn_reflns_limit_k_min       -49
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_number            94929
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         76.239
_diffrn_reflns_theta_min         3.180
_diffrn_source                   'micro-focus sealed X-ray tube'
_exptl_absorpt_coefficient_mu    1.830
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.653
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details
;
(CrysAlis PRO; Rigaku OD, 2018)
;
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.324
_exptl_crystal_description       prism
_exptl_crystal_F_000             3472
_exptl_crystal_size_max          0.166
_exptl_crystal_size_mid          0.161
_exptl_crystal_size_min          0.085
_refine_diff_density_max         0.415
_refine_diff_density_min         -0.553
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.036
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     1079
_refine_ls_number_reflns         17036
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.036
_refine_ls_R_factor_all          0.0356
_refine_ls_R_factor_gt           0.0331
_refine_ls_shift/su_max          0.003
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0481P)^2^+3.5049P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0900
_refine_ls_wR_factor_ref         0.0921
_reflns_number_gt                15740
_reflns_number_total             17036
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            hb7782sup1.cif
_cod_data_source_block           I
_cod_depositor_comments
;

2019-09-02
Z value and formula fixed to values more according to usual
chemical conventions.                 miguel
;
_cod_original_formula_moiety     '4(C18 H15 O P), 2(C14 H10 O4 S)'
_cod_original_formula_iupac      '4C18 H15 O P, 2C14 H10 O4 S'
_cod_original_formula_sum        'C100 H80 O12 P4 S2'
_cod_original_formula_units_Z    4
_cod_original_formula_weight     1661.64
_cod_database_code               2242725
_cod_database_fobs_code          2242725
_shelx_hkl_checksum              41655
_shelx_res_checksum              65994