#------------------------------------------------------------------------------
#$Date: 2018-12-12 05:37:30 +0200 (Wed, 12 Dec 2018) $
#$Revision: 212550 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/02/14/2021414.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/. The original data for this entry
# were provided by IUCr Journals, http://journals.iucr.org/.
#
# The file may be used within the scientific community so long as
# proper attribution is given to the journal article from which the
# data were obtained.
#
data_2021414
loop_
_publ_author_name
'Tan, Sang Loon'
'Tiekink, Edward R. T.'
_publ_section_title
;
 A 1:2 co-crystal of 2,2′-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 et al.,
2009)
and Mercury (Macrae et al., 2006)
;
_computing_publication_material
;
publCIF (Westrip, 2010)
;
_computing_structure_refinement
;
SHELXL (Sheldrick, 2015a)
;
_computing_structure_solution
;
SHELXT (Sheldrick, 2015b)
;
_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       'ω 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/[σ²(Fo²)+(0.0597P)²+4.0853P] where P=(Fo²+2Fc²)/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 > 2σ(I)'
_cod_data_source_file            hb7790sup1.cif
_cod_data_source_block           I
_cod_database_code               2021414
_shelx_space_group_comment
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y, -z+1/2'
'x+1/2, y+1/2, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y, z-1/2'
'-x+1/2, -y+1/2, -z'
'x+1/2, -y+1/2, z-1/2'
loop_
_atom_site_type_symbol
_atom_site_label
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_calc_flag
_atom_site_occupancy
S S1 0.50125(5) 0.53534(3) 0.29507(2) 0.01870(14) Uani d 1
O O1 0.29643(16) 0.49404(10) 0.46525(5) 0.0239(3) Uani d 1
H H1o 0.328(3) 0.544(2) 0.4890(12) 0.042(7) Uiso d 1
O O2 0.46078(15) 0.57402(9) 0.40809(5) 0.0213(3) Uani d 1
O O3 0.52518(17) 0.72548(10) 0.48274(6) 0.0260(3) Uani d 1
H H3o 0.502(4) 0.676(2) 0.4589(13) 0.053(8) Uiso d 1
O O4 0.35583(16) 0.64485(9) 0.53788(5) 0.0237(3) Uani d 1
C C1 0.3639(2) 0.50608(12) 0.41556(7) 0.0179(3) Uani d 1
C C2 0.3123(2) 0.43148(12) 0.36912(7) 0.0175(3) Uani d 1
C C3 0.3622(2) 0.43865(12) 0.31172(7) 0.0172(3) Uani d 1
C C4 0.3046(2) 0.36819(13) 0.26917(7) 0.0192(3) Uani d 1
H H4 0.336143 0.372512 0.231068 0.023 Uiso calc 1
C C5 0.2004(2) 0.29140(13) 0.28321(8) 0.0213(4) Uani d 1
H H5 0.162961 0.244879 0.254423 0.026 Uiso calc 1
C C6 0.1519(2) 0.28379(13) 0.33971(8) 0.0220(4) Uani d 1
H H6 0.083137 0.232083 0.349054 0.026 Uiso calc 1
C C7 0.2070(2) 0.35389(13) 0.38213(8) 0.0208(3) Uani d 1
H H7 0.173415 0.349359 0.419926 0.025 Uiso calc 1
C C8 0.4462(2) 0.71641(13) 0.53011(7) 0.0195(3) Uani d 1
C C9 0.4761(2) 0.79789(13) 0.57426(7) 0.0196(3) Uani d 1
C C10 0.4020(2) 0.79189(13) 0.62667(7) 0.0212(4) Uani d 1
H H10 0.331481 0.739174 0.632630 0.025 Uiso calc 1
C C11 0.4340(2) 0.86479(14) 0.66992(8) 0.0234(4) Uani d 1
H H11 0.384929 0.860972 0.704986 0.028 Uiso calc 1
C C12 0.5395(2) 0.94372(14) 0.66082(8) 0.0238(4) Uani d 1
H H12 0.561938 0.992032 0.690087 0.029 Uiso calc 1
C C13 0.6111(2) 0.95056(14) 0.60843(8) 0.0247(4) Uani d 1
H H13 0.680059 1.004025 0.602298 0.030 Uiso calc 1
C C14 0.5801(2) 0.87766(13) 0.56496(8) 0.0225(4) Uani d 1
H H14 0.628625 0.882052 0.529801 0.027 Uiso calc 1
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.3331 0.5567 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
-4 5 0 0.0374
0 0 -1 0.0317
-1 -1 5 0.0513
1 1 -5 0.0591
0 0 1 0.0307
-5 -2 -4 0.0728
0 -5 1 0.0965
0 5 -1 0.0599
-1 -1 -5 0.0569
5 2 4 0.0753
-3 5 -3 0.0376
0 -5 -1 0.0977
-5 -3 -2 0.0829
5 1 2 0.0692
3 -5 -1 0.0683
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle_site_symmetry_3
_geom_angle
C3 S1 S1 2_655 105.68(6)
C1 O1 H1o . 107.9(18)
C8 O3 H3o . 110(2)
O1 C1 C2 . 114.38(14)
O2 C1 O1 . 122.96(15)
O2 C1 C2 . 122.65(15)
C3 C2 C1 . 121.58(15)
C7 C2 C1 . 119.01(15)
C7 C2 C3 . 119.38(15)
C2 C3 S1 . 119.84(12)
C4 C3 S1 . 121.18(13)
C4 C3 C2 . 118.96(15)
C3 C4 H4 . 119.7
C5 C4 C3 . 120.63(16)
C5 C4 H4 . 119.7
C4 C5 H5 . 119.7
C6 C5 C4 . 120.52(16)
C6 C5 H5 . 119.7
C5 C6 H6 . 120.3
C7 C6 C5 . 119.36(16)
C7 C6 H6 . 120.3
C2 C7 H7 . 119.4
C6 C7 C2 . 121.15(16)
C6 C7 H7 . 119.4
O3 C8 C9 . 115.08(15)
O4 C8 O3 . 122.88(16)
O4 C8 C9 . 122.04(15)
C10 C9 C8 . 118.64(16)
C10 C9 C14 . 120.14(16)
C14 C9 C8 . 121.19(15)
C9 C10 H10 . 120.1
C11 C10 C9 . 119.78(17)
C11 C10 H10 . 120.1
C10 C11 H11 . 120.0
C10 C11 C12 . 119.96(17)
C12 C11 H11 . 120.0
C11 C12 H12 . 119.9
C13 C12 C11 . 120.29(17)
C13 C12 H12 . 119.9
C12 C13 H13 . 120.0
C12 C13 C14 . 120.09(17)
C14 C13 H13 . 120.0
C9 C14 H14 . 120.1
C13 C14 C9 . 119.73(16)
C13 C14 H14 . 120.1
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_site_symmetry_2
_geom_bond_distance
S1 S1 2_655 2.0446(8)
S1 C3 . 1.7889(17)
O1 H1o . 0.88(3)
O1 C1 . 1.317(2)
O2 C1 . 1.229(2)
O3 H3o . 0.87(3)
O3 C8 . 1.318(2)
O4 C8 . 1.233(2)
C1 C2 . 1.479(2)
C2 C3 . 1.409(2)
C2 C7 . 1.400(2)
C3 C4 . 1.395(2)
C4 H4 . 0.9300
C4 C5 . 1.393(2)
C5 H5 . 0.9300
C5 C6 . 1.385(2)
C6 H6 . 0.9300
C6 C7 . 1.384(2)
C7 H7 . 0.9300
C8 C9 . 1.481(2)
C9 C10 . 1.393(2)
C9 C14 . 1.395(2)
C10 H10 . 0.9300
C10 C11 . 1.387(2)
C11 H11 . 0.9300
C11 C12 . 1.393(3)
C12 H12 . 0.9300
C12 C13 . 1.383(3)
C13 H13 . 0.9300
C13 C14 . 1.390(3)
C14 H14 . 0.9300
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_site_symmetry_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
O1 H1O O4 . 0.88(3) 1.74(3) 2.6134(17) 170(2)
O3 H3O O2 . 0.86(3) 1.79(3) 2.6535(18) 178(4)
C7 H7 O3 3_445 0.93 2.57 3.329(2) 139
C14 H14 O1 3 0.93 2.59 3.395(2) 145

_cod_database_fobs_code 2021414
