#------------------------------------------------------------------------------
#$Date: 2025-08-22 15:50:14 +0300 (Fri, 22 Aug 2025) $
#$Revision: 301863 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/20/29/7202972.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/
#
# All data on this site have been placed in the public domain by the
# contributors.
#
data_7202972
loop_
_publ_author_name
'Broker, Grant A.'
'Tiekink, Edward R. T.'
_publ_section_title
;
 Co-crystal formation between 2,2′-dithiodibenzoic acid and each
 of 4,4′-bipyridine, trans-1,2-bis(4-pyridyl)ethene and
 1,2-bis(4-pyridyl)ethane
;
_journal_issue                   11
_journal_name_full               CrystEngComm
_journal_page_first              1096
_journal_paper_doi               10.1039/b707690h
_journal_volume                  9
_journal_year                    2007
_chemical_formula_moiety         'C26 H22 N2 O4 S2'
_chemical_formula_sum            'C26 H22 N2 O4 S2'
_chemical_formula_weight         490.58
_space_group_IT_number           15
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-C 2yc'
_symmetry_space_group_name_H-M   'C 1 2/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90
_cell_angle_beta                 125.715(2)
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   28.8615(9)
_cell_length_b                   10.1880(4)
_cell_length_c                   19.9562(8)
_cell_measurement_reflns_used    5604
_cell_measurement_temperature    120(2)
_cell_measurement_theta_max      27.5
_cell_measurement_theta_min      1.0
_cell_volume                     4764.4(3)
_computing_cell_refinement
'DENZO (Otwinowski & Minor, 1997) & COLLECT (Hooft, R.W.W., 1998)'
_computing_data_collection       'COLLECT (Hooft, R.W.W., 1998)'
_computing_data_reduction
'DENZO (Otwinowski & Minor, 1997) & COLLECT (Hooft, R.W.W., 1998)'
_computing_molecular_graphics
'ORTEPII (Johnson, 1976) and DIAMOND (Crystal Impact, 2006'
_computing_publication_material  SHELXL97
_computing_structure_refinement  'SHELXL97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 1997)'
_diffrn_ambient_temperature      120(2)
_diffrn_detector_area_resol_mean 9.091
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type  'Bruker-Nonius 95mm CCD camera on κ-goniostat'
_diffrn_measurement_method       'φ & ω scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'Bruker-Nonius FR591 rotating anode'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71069
_diffrn_reflns_av_R_equivalents  0.064
_diffrn_reflns_av_sigmaI/netI    0.056
_diffrn_reflns_limit_h_max       34
_diffrn_reflns_limit_h_min       -36
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       24
_diffrn_reflns_limit_l_min       -25
_diffrn_reflns_number            27316
_diffrn_reflns_theta_full        26.5
_diffrn_reflns_theta_max         26.5
_diffrn_reflns_theta_min         1.7
_diffrn_standards_decay_%        0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.260
_exptl_absorpt_correction_T_max  1
_exptl_absorpt_correction_T_min  0.736
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS V2.10 (Sheldrick, 2003)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.368
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             2048
_exptl_crystal_size_max          0.20
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.08
_refine_diff_density_max         0.62
_refine_diff_density_min         -0.32
_refine_diff_density_rms         0.075
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.06
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     350
_refine_ls_number_reflns         4938
_refine_ls_number_restraints     2
_refine_ls_restrained_S_all      1.06
_refine_ls_R_factor_all          0.096
_refine_ls_R_factor_gt           0.053
_refine_ls_shift/su_max          <0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0769P)²+3.6574P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.130
_refine_ls_wR_factor_ref         0.153
_reflns_number_gt                3297
_reflns_number_total             4938
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            b707690h.txt
_cod_data_source_block
(HO2C)C6H4SSC6H4(CO2H).{1,2-bis(pyridine)ethane}(3)
_cod_original_sg_symbol_H-M      C2/c
_cod_database_code               7202972
loop_
_symmetry_equiv_pos_as_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_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
S1 S 0.11207(3) 0.86354(7) 0.43387(4) 0.0388(2) Uani 1 1 d . . .
S2 S 0.12251(3) 1.04926(7) 0.40438(5) 0.0418(2) Uani 1 1 d . . .
O1 O 0.10724(10) 0.5484(2) 0.57932(14) 0.0488(5) Uani 1 1 d D . .
H1O H 0.0866(13) 0.487(3) 0.5479(19) 0.073 Uiso 1 1 d D . .
O2 O 0.08147(8) 0.6373(2) 0.46002(13) 0.0457(5) Uani 1 1 d . . .
O3 O 0.19967(10) 1.36825(19) 0.35201(14) 0.0465(5) Uani 1 1 d D . .
H3O H 0.1748(11) 1.427(3) 0.328(2) 0.070 Uiso 1 1 d D . .
O4 O 0.12529(8) 1.2792(2) 0.34296(12) 0.0471(5) Uani 1 1 d . . .
N2 N -0.14157(11) -0.4173(2) 0.20588(15) 0.0464(6) Uani 1 1 d . A .
N1 N 0.04568(12) 0.3528(2) 0.48400(18) 0.0478(7) Uani 0.731(5) 1 d P A 1
C3 C -0.02919(14) 0.1518(3) 0.3831(2) 0.0468(8) Uani 0.731(5) 1 d P A 1
C1 C 0.02789(19) 0.3356(5) 0.4028(3) 0.0437(12) Uani 0.731(5) 1 d P A 1
H1 H 0.0417 0.3946 0.3814 0.052 Uiso 0.731(5) 1 calc PR A 1
C2 C -0.0090(2) 0.2363(5) 0.3521(3) 0.0431(12) Uani 0.731(5) 1 d P A 1
H2 H -0.0199 0.2269 0.2972 0.052 Uiso 0.731(5) 1 calc PR A 1
C4 C -0.01365(16) 0.1698(4) 0.4614(2) 0.0379(11) Uani 0.731(5) 1 d P A 1
H4 H -0.0282 0.1139 0.4832 0.045 Uiso 0.731(5) 1 calc PR A 1
C5 C 0.02335(17) 0.2700(4) 0.5085(2) 0.0396(11) Uani 0.731(5) 1 d P A 1
H5 H 0.0336 0.2803 0.5629 0.048 Uiso 0.731(5) 1 calc PR A 1
N1' N 0.04568(12) 0.3528(2) 0.48400(18) 0.0478(7) Uani 0.269(5) 1 d P A 2
C3' C -0.02919(14) 0.1518(3) 0.3831(2) 0.0468(8) Uani 0.269(5) 1 d P A 2
C1A C 0.0041(7) 0.3761(13) 0.4233(11) 0.069(5) Uani 0.269(5) 1 d P A 2
H1A H -0.0080 0.4647 0.4086 0.083 Uiso 0.269(5) 1 calc PR A 2
C2A C -0.0296(7) 0.2749(15) 0.3699(11) 0.075(5) Uani 0.269(5) 1 d P A 2
H2A H -0.0574 0.3015 0.3145 0.090 Uiso 0.269(5) 1 calc PR A 2
C4A C 0.0313(7) 0.1258(13) 0.4656(12) 0.082(5) Uani 0.269(5) 1 d P A 2
H4A H 0.0443 0.0377 0.4795 0.098 Uiso 0.269(5) 1 calc PR A 2
C5A C 0.0676(6) 0.2273(13) 0.5205(9) 0.064(4) Uani 0.269(5) 1 d P A 2
H5A H 0.1016 0.2132 0.5741 0.077 Uiso 0.269(5) 1 calc PR A 2
C6 C -0.07091(14) 0.0441(3) 0.3292(2) 0.0494(8) Uani 1 1 d . . .
H6A H -0.0890 0.0098 0.3552 0.059 Uiso 1 1 calc R A 1
H6B H -0.1013 0.0815 0.2749 0.059 Uiso 1 1 calc R A 1
C7 C -0.04247(13) -0.0667(3) 0.3168(2) 0.0497(8) Uani 1 1 d . A .
H7A H -0.0077 -0.0917 0.3712 0.060 Uiso 1 1 calc R . .
H7B H -0.0302 -0.0344 0.2826 0.060 Uiso 1 1 calc R . .
C8 C -0.07820(12) -0.1876(3) 0.27654(18) 0.0424(7) Uani 1 1 d . . .
C9 C -0.13709(12) -0.1888(3) 0.23465(18) 0.0418(7) Uani 1 1 d . A .
H9 H -0.1568 -0.1106 0.2298 0.050 Uiso 1 1 calc R . .
C10 C -0.16667(13) -0.3039(3) 0.20018(18) 0.0422(7) Uani 1 1 d . . .
H10 H -0.2070 -0.3025 0.1709 0.051 Uiso 1 1 calc R A .
C11 C -0.08528(15) -0.4157(4) 0.2446(2) 0.0650(10) Uani 1 1 d . . .
H11 H -0.0668 -0.4948 0.2475 0.078 Uiso 1 1 calc R A .
C12 C -0.05277(14) -0.3052(4) 0.2805(2) 0.0612(10) Uani 1 1 d . A .
H12 H -0.0126 -0.3094 0.3082 0.073 Uiso 1 1 calc R . .
C14 C 0.14376(10) 0.7576(3) 0.58333(17) 0.0340(6) Uani 1 1 d . . .
C15 C 0.14798(10) 0.8662(3) 0.54341(17) 0.0330(6) Uani 1 1 d . . .
C16 C 0.18199(11) 0.9718(3) 0.59103(18) 0.0379(7) Uani 1 1 d . . .
H16 H 0.1853 1.0453 0.5648 0.045 Uiso 1 1 calc R . .
C17 C 0.21100(13) 0.9715(3) 0.67556(19) 0.0462(8) Uani 1 1 d . . .
H17 H 0.2338 1.0449 0.7069 0.055 Uiso 1 1 calc R . .
C18 C 0.20716(13) 0.8645(3) 0.71518(19) 0.0477(8) Uani 1 1 d . . .
H18 H 0.2274 0.8640 0.7735 0.057 Uiso 1 1 calc R . .
C19 C 0.17356(12) 0.7586(3) 0.66880(18) 0.0411(7) Uani 1 1 d . . .
H19 H 0.1708 0.6854 0.6957 0.049 Uiso 1 1 calc R . .
C13 C 0.10760(11) 0.6425(3) 0.53468(19) 0.0379(7) Uani 1 1 d . . .
C21 C 0.21204(12) 1.1594(3) 0.40913(16) 0.0329(6) Uani 1 1 d . . .
C20 C 0.19305(11) 1.0486(3) 0.42846(16) 0.0334(6) Uani 1 1 d . . .
C22 C 0.26830(13) 1.1611(3) 0.43336(18) 0.0403(7) Uani 1 1 d . . .
H22 H 0.2816 1.2357 0.4208 0.048 Uiso 1 1 calc R . .
C23 C 0.30490(12) 1.0574(3) 0.47496(18) 0.0395(7) Uani 1 1 d . . .
H23 H 0.3432 1.0612 0.4917 0.047 Uiso 1 1 calc R . .
C24 C 0.28530(12) 0.9478(3) 0.49209(17) 0.0377(7) Uani 1 1 d . . .
H24 H 0.3099 0.8750 0.5196 0.045 Uiso 1 1 calc R . .
C25 C 0.22989(11) 0.9438(3) 0.46928(16) 0.0366(7) Uani 1 1 d . . .
H25 H 0.2169 0.8683 0.4817 0.044 Uiso 1 1 calc R . .
C26 C 0.17443(13) 1.2739(3) 0.36472(16) 0.0373(7) Uani 1 1 d . . .
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 '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'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C15 S1 S2 104.97(9) . . ?
C20 S2 S1 104.63(9) . . ?
C10 N2 C11 117.2(3) . . ?
C5 N1 C1 115.0(3) . . ?
C4 C3 C2 119.3(3) . . ?
C4 C3 C6 120.3(3) . . ?
C2 C3 C6 120.3(3) . . ?
C2 C1 N1 123.1(4) . . ?
C3 C2 C1 118.3(4) . . ?
C3 C4 C5 119.2(3) . . ?
N1 C5 C4 125.0(4) . . ?
C1A N1 C5A 128.0(9) . . ?
C2A C3 C6 130.9(7) . . ?
C2A C3 C4A 104.6(8) . . ?
C6 C3 C4A 123.9(5) . . ?
N1 C1A C2A 119.9(13) . . ?
C3 C2A C1A 130.5(14) . . ?
C5A C4A C3 123.5(11) . . ?
C4A C5A N1 110.6(12) . . ?
C7 C6 C3 112.2(3) . . ?
C7 C6 C3 112.2(3) . . ?
C3 C6 C3 0.0(5) . . ?
C6 C7 C8 115.7(2) . . ?
C12 C8 C9 116.7(3) . . ?
C12 C8 C7 120.3(3) . . ?
C9 C8 C7 123.1(3) . . ?
C10 C9 C8 119.5(3) . . ?
N2 C10 C9 123.3(3) . . ?
N2 C11 C12 123.0(3) . . ?
C11 C12 C8 120.2(3) . . ?
C19 C14 C15 119.5(3) . . ?
C19 C14 C13 120.0(3) . . ?
C15 C14 C13 120.5(2) . . ?
C16 C15 C14 118.7(3) . . ?
C16 C15 S1 121.4(2) . . ?
C14 C15 S1 119.9(2) . . ?
C17 C16 C15 121.1(3) . . ?
C16 C17 C18 120.4(3) . . ?
C19 C18 C17 119.3(3) . . ?
C18 C19 C14 121.1(3) . . ?
O2 C13 O1 123.7(3) . . ?
O2 C13 C14 122.0(2) . . ?
O1 C13 C14 114.3(3) . . ?
C22 C21 C20 118.4(3) . . ?
C22 C21 C26 119.6(2) . . ?
C20 C21 C26 122.0(2) . . ?
C25 C20 C21 119.5(2) . . ?
C25 C20 S2 121.3(2) . . ?
C21 C20 S2 119.1(2) . . ?
C23 C22 C21 121.8(3) . . ?
C22 C23 C24 119.2(3) . . ?
C23 C24 C25 120.2(3) . . ?
C24 C25 C20 120.8(3) . . ?
O4 C26 O3 123.9(3) . . ?
O4 C26 C21 122.8(2) . . ?
O3 C26 C21 113.3(2) . . ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
S1 C15 1.791(3) . ?
S1 S2 2.0552(10) . ?
S2 C20 1.798(3) . ?
O1 C13 1.313(3) . ?
O2 C13 1.216(3) . ?
O3 C26 1.317(3) . ?
O4 C26 1.218(3) . ?
N2 C10 1.333(4) . ?
N2 C11 1.331(4) . ?
N1 C5 1.317(4) . ?
N1 C1 1.395(5) . ?
C3 C4 1.362(5) . ?
C3 C2 1.374(5) . ?
C3 C6 1.515(4) . ?
C1 C2 1.387(6) . ?
C4 C5 1.377(5) . ?
N1 C1A 1.125(15) . ?
N1 C5A 1.425(14) . ?
C3 C2A 1.281(15) . ?
C3 C6 1.515(4) . ?
C3 C4A 1.573(18) . ?
C1A C2A 1.391(19) . ?
C4A C5A 1.42(2) . ?
C6 C7 1.500(4) . ?
C7 C8 1.503(4) . ?
C8 C12 1.383(4) . ?
C8 C9 1.389(4) . ?
C9 C10 1.376(4) . ?
C11 C12 1.370(5) . ?
C14 C19 1.392(4) . ?
C14 C15 1.409(4) . ?
C14 C13 1.492(4) . ?
C15 C16 1.391(4) . ?
C16 C17 1.378(4) . ?
C17 C18 1.388(4) . ?
C18 C19 1.383(4) . ?
C21 C22 1.398(4) . ?
C21 C20 1.403(4) . ?
C21 C26 1.483(4) . ?
C20 C25 1.387(4) . ?
C22 C23 1.377(4) . ?
C23 C24 1.382(4) . ?
C24 C25 1.384(4) . ?
loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C15 S1 S2 C20 80.80(12) . . . . ?
C5 N1 C1 C2 -2.2(7) . . . . ?
C4 C3 C2 C1 1.5(7) . . . . ?
C6 C3 C2 C1 178.2(4) . . . . ?
N1 C1 C2 C3 0.6(8) . . . . ?
C2 C3 C4 C5 -1.9(6) . . . . ?
C6 C3 C4 C5 -178.6(3) . . . . ?
C1 N1 C5 C4 1.8(6) . . . . ?
C3 C4 C5 N1 0.2(6) . . . . ?
C5A N1 C1A C2A -8(3) . . . . ?
C6 C3 C2A C1A 169.5(16) . . . . ?
C4A C3 C2A C1A -20(3) . . . . ?
N1 C1A C2A C3 18(4) . . . . ?
C2A C3 C4A C5A 15.6(19) . . . . ?
C6 C3 C4A C5A -172.6(11) . . . . ?
C3 C4A C5A N1 -9.5(19) . . . . ?
C1A N1 C5A C4A 5(2) . . . . ?
C4 C3 C6 C7 -108.7(4) . . . . ?
C2 C3 C6 C7 74.7(4) . . . . ?
C4 C3 C6 C3 0(100) . . . . ?
C2 C3 C6 C3 0(28) . . . . ?
C2A C3 C6 C7 124.5(15) . . . . ?
C4A C3 C6 C7 -45.0(8) . . . . ?
C2A C3 C6 C3 0(100) . . . . ?
C4A C3 C6 C3 0(100) . . . . ?
C3 C6 C7 C8 169.9(3) . . . . ?
C3 C6 C7 C8 169.9(3) . . . . ?
C6 C7 C8 C12 -163.9(3) . . . . ?
C6 C7 C8 C9 15.7(4) . . . . ?
C12 C8 C9 C10 0.3(4) . . . . ?
C7 C8 C9 C10 -179.4(3) . . . . ?
C11 N2 C10 C9 -2.5(5) . . . . ?
C8 C9 C10 N2 1.2(5) . . . . ?
C10 N2 C11 C12 2.4(5) . . . . ?
N2 C11 C12 C8 -1.0(6) . . . . ?
C9 C8 C12 C11 -0.3(5) . . . . ?
C7 C8 C12 C11 179.3(3) . . . . ?
C19 C14 C15 C16 0.0(4) . . . . ?
C13 C14 C15 C16 179.8(2) . . . . ?
C19 C14 C15 S1 177.6(2) . . . . ?
C13 C14 C15 S1 -2.6(3) . . . . ?
S2 S1 C15 C16 -9.5(2) . . . . ?
S2 S1 C15 C14 172.94(18) . . . . ?
C14 C15 C16 C17 -0.3(4) . . . . ?
S1 C15 C16 C17 -177.9(2) . . . . ?
C15 C16 C17 C18 0.5(4) . . . . ?
C16 C17 C18 C19 -0.5(4) . . . . ?
C17 C18 C19 C14 0.2(4) . . . . ?
C15 C14 C19 C18 0.1(4) . . . . ?
C13 C14 C19 C18 -179.7(3) . . . . ?
C19 C14 C13 O2 -179.1(3) . . . . ?
C15 C14 C13 O2 1.0(4) . . . . ?
C19 C14 C13 O1 0.1(4) . . . . ?
C15 C14 C13 O1 -179.7(2) . . . . ?
C22 C21 C20 C25 -1.2(4) . . . . ?
C26 C21 C20 C25 179.3(2) . . . . ?
C22 C21 C20 S2 175.64(19) . . . . ?
C26 C21 C20 S2 -3.9(3) . . . . ?
S1 S2 C20 C25 -8.2(2) . . . . ?
S1 S2 C20 C21 175.04(18) . . . . ?
C20 C21 C22 C23 0.3(4) . . . . ?
C26 C21 C22 C23 179.8(3) . . . . ?
C21 C22 C23 C24 1.1(4) . . . . ?
C22 C23 C24 C25 -1.4(4) . . . . ?
C23 C24 C25 C20 0.5(4) . . . . ?
C21 C20 C25 C24 0.8(4) . . . . ?
S2 C20 C25 C24 -175.9(2) . . . . ?
C22 C21 C26 O4 -179.0(3) . . . . ?
C20 C21 C26 O4 0.5(4) . . . . ?
C22 C21 C26 O3 0.6(3) . . . . ?
C20 C21 C26 O3 -179.9(2) . . . . ?
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 PubChem 139194962
