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#$Date: 2025-08-22 15:50:14 +0300 (Fri, 22 Aug 2025) $
#$Revision: 301863 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/20/29/7202970.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_7202970
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         'C14 H10 S2, C10 H8 N2'
_chemical_formula_sum            'C24 H18 N2 O4 S2'
_chemical_formula_weight         462.52
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 1 21/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                 95.04(3)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   9.1441(18)
_cell_length_b                   13.157(3)
_cell_length_c                   17.564(4)
_cell_measurement_reflns_used    6696
_cell_measurement_temperature    173(2)
_cell_measurement_theta_max      27.5
_cell_measurement_theta_min      2.2
_cell_volume                     2104.9(8)
_computing_cell_refinement       CrystalClear
_computing_data_collection       'CrystalClear (Rigaku, 2005)'
_computing_data_reduction        CrystalClear
_computing_molecular_graphics
'ORTEPII (Johnson, 1976) & DIAMOND (Crystal Impact, 2006)'
_computing_publication_material  SHELXL97
_computing_structure_refinement  'SHELXL97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 1997)'
_diffrn_ambient_temperature      173(2)
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type  AFC12Κ/SATURN724
_diffrn_measurement_method       ω
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71070
_diffrn_reflns_av_R_equivalents  0.061
_diffrn_reflns_av_sigmaI/netI    0.034
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_number            33721
_diffrn_reflns_theta_full        26.5
_diffrn_reflns_theta_max         26.5
_diffrn_reflns_theta_min         2.2
_diffrn_standards_decay_%        '< 1'
_diffrn_standards_interval_count 0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.289
_exptl_absorpt_correction_T_max  1
_exptl_absorpt_correction_T_min  0.789
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'ABSCOR (Higashi, 1995)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.460
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             960
_exptl_crystal_size_max          0.41
_exptl_crystal_size_mid          0.22
_exptl_crystal_size_min          0.11
_refine_diff_density_max         0.26
_refine_diff_density_min         -0.26
_refine_diff_density_rms         0.056
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.13
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     295
_refine_ls_number_reflns         4366
_refine_ls_number_restraints     2
_refine_ls_restrained_S_all      1.13
_refine_ls_R_factor_all          0.050
_refine_ls_R_factor_gt           0.045
_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)+(0.0342P)²+1.4641P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.094
_refine_ls_wR_factor_ref         0.097
_reflns_number_gt                4099
_reflns_number_total             4366
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            b707690h.txt
_cod_data_source_block           (HO2C)C6H4SSC6H4(CO2H).4,4'-bipyridine(1)
_cod_original_sg_symbol_H-M      P21/c
_cod_database_code               7202970
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -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 -0.12692(5) 0.34943(4) 0.32808(3) 0.01857(13) Uani 1 1 d . . .
S2 S -0.31684(5) 0.30571(4) 0.37367(3) 0.01858(13) Uani 1 1 d . . .
O1 O 0.15671(16) 0.53225(12) 0.18889(9) 0.0323(4) Uani 1 1 d D . .
H1O H 0.2363(16) 0.5037(19) 0.1812(16) 0.048 Uiso 1 1 d D . .
O2 O 0.11992(14) 0.39628(10) 0.26144(8) 0.0213(3) Uani 1 1 d . . .
O3 O -0.65781(15) 0.29764(12) 0.53707(8) 0.0259(3) Uani 1 1 d D . .
H3O H -0.7338(16) 0.2637(16) 0.5242(14) 0.039 Uiso 1 1 d D . .
O4 O -0.56356(16) 0.23810(11) 0.43270(8) 0.0268(3) Uani 1 1 d . . .
N1 N 0.40546(17) 0.45635(13) 0.15422(10) 0.0220(4) Uani 1 1 d . . .
N2 N 1.08367(19) 0.29069(14) 0.03087(10) 0.0250(4) Uani 1 1 d . . .
C1 C 0.4596(2) 0.36501(16) 0.17421(12) 0.0241(4) Uani 1 1 d . . .
H1 H 0.4046 0.3224 0.2048 0.029 Uiso 1 1 calc R . .
C2 C 0.5919(2) 0.32955(15) 0.15254(12) 0.0215(4) Uani 1 1 d . . .
H2 H 0.6273 0.2645 0.1689 0.026 Uiso 1 1 calc R . .
C3 C 0.6732(2) 0.39012(15) 0.10636(10) 0.0172(4) Uani 1 1 d . . .
C4 C 0.6172(2) 0.48559(15) 0.08659(11) 0.0196(4) Uani 1 1 d . . .
H4 H 0.6696 0.5299 0.0560 0.023 Uiso 1 1 calc R . .
C5 C 0.4848(2) 0.51583(15) 0.11166(11) 0.0210(4) Uani 1 1 d . . .
H5 H 0.4485 0.5816 0.0981 0.025 Uiso 1 1 calc R . .
C6 C 0.8150(2) 0.35433(15) 0.08003(11) 0.0191(4) Uani 1 1 d . . .
C7 C 0.8639(2) 0.38953(16) 0.01193(11) 0.0224(4) Uani 1 1 d . . .
H7 H 0.8061 0.4362 -0.0191 0.027 Uiso 1 1 calc R . .
C8 C 0.9972(2) 0.35609(17) -0.01020(12) 0.0247(5) Uani 1 1 d . . .
H8 H 1.0288 0.3808 -0.0569 0.030 Uiso 1 1 calc R . .
C9 C 1.0353(2) 0.25594(18) 0.09573(12) 0.0273(5) Uani 1 1 d . . .
H9 H 1.0950 0.2089 0.1254 0.033 Uiso 1 1 calc R . .
C10 C 0.9037(2) 0.28467(16) 0.12192(12) 0.0236(4) Uani 1 1 d . . .
H10 H 0.8739 0.2572 0.1681 0.028 Uiso 1 1 calc R . .
C11 C 0.0793(2) 0.47734(15) 0.23339(11) 0.0192(4) Uani 1 1 d . . .
C12 C -0.0655(2) 0.52332(14) 0.24572(10) 0.0171(4) Uani 1 1 d . . .
C13 C -0.1696(2) 0.47132(14) 0.28548(10) 0.0163(4) Uani 1 1 d . . .
C14 C -0.3062(2) 0.51671(15) 0.29136(11) 0.0184(4) Uani 1 1 d . . .
H14 H -0.3778 0.4824 0.3178 0.022 Uiso 1 1 calc R . .
C15 C -0.3385(2) 0.61072(15) 0.25921(11) 0.0192(4) Uani 1 1 d . . .
H15 H -0.4330 0.6395 0.2629 0.023 Uiso 1 1 calc R . .
C16 C -0.2356(2) 0.66369(15) 0.22173(11) 0.0198(4) Uani 1 1 d . . .
H16 H -0.2577 0.7289 0.2005 0.024 Uiso 1 1 calc R . .
C17 C -0.0998(2) 0.61962(15) 0.21588(10) 0.0184(4) Uani 1 1 d . . .
H17 H -0.0279 0.6558 0.1909 0.022 Uiso 1 1 calc R . .
C18 C -0.3147(2) 0.37448(14) 0.46227(10) 0.0169(4) Uani 1 1 d . . .
C19 C -0.4302(2) 0.36177(14) 0.50921(11) 0.0163(4) Uani 1 1 d . . .
C20 C -0.4287(2) 0.41719(15) 0.57692(11) 0.0201(4) Uani 1 1 d . . .
H20 H -0.5063 0.4082 0.6089 0.024 Uiso 1 1 calc R . .
C21 C -0.3172(2) 0.48484(16) 0.59877(11) 0.0223(4) Uani 1 1 d . . .
H21 H -0.3179 0.5219 0.6452 0.027 Uiso 1 1 calc R . .
C22 C -0.2049(2) 0.49767(16) 0.55196(12) 0.0230(4) Uani 1 1 d . . .
H22 H -0.1277 0.5441 0.5663 0.028 Uiso 1 1 calc R . .
C23 C -0.2035(2) 0.44353(15) 0.48439(11) 0.0210(4) Uani 1 1 d . . .
H23 H -0.1258 0.4536 0.4527 0.025 Uiso 1 1 calc R . .
C24 C -0.5561(2) 0.29282(14) 0.48845(11) 0.0188(4) 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
C13 S1 S2 104.56(7) . . ?
C18 S2 S1 104.51(7) . . ?
C11 O1 H1O 111.6(19) . . ?
C24 O3 H3O 114.4(18) . . ?
C5 N1 C1 117.81(17) . . ?
C9 N2 C8 117.11(18) . . ?
N1 C1 C2 123.04(19) . . ?
N1 C1 H1 118.5 . . ?
C2 C1 H1 118.5 . . ?
C1 C2 C3 119.42(19) . . ?
C1 C2 H2 120.3 . . ?
C3 C2 H2 120.3 . . ?
C4 C3 C2 117.22(18) . . ?
C4 C3 C6 121.32(18) . . ?
C2 C3 C6 121.45(18) . . ?
C3 C4 C5 119.64(18) . . ?
C3 C4 H4 120.2 . . ?
C5 C4 H4 120.2 . . ?
N1 C5 C4 122.83(19) . . ?
N1 C5 H5 118.6 . . ?
C4 C5 H5 118.6 . . ?
C7 C6 C10 117.19(18) . . ?
C7 C6 C3 121.01(18) . . ?
C10 C6 C3 121.80(18) . . ?
C6 C7 C8 119.54(19) . . ?
C6 C7 H7 120.2 . . ?
C8 C7 H7 120.2 . . ?
N2 C8 C7 123.18(19) . . ?
N2 C8 H8 118.4 . . ?
C7 C8 H8 118.4 . . ?
N2 C9 C10 123.6(2) . . ?
N2 C9 H9 118.2 . . ?
C10 C9 H9 118.2 . . ?
C9 C10 C6 119.34(19) . . ?
C9 C10 H10 120.3 . . ?
C6 C10 H10 120.3 . . ?
O2 C11 O1 124.01(18) . . ?
O2 C11 C12 122.71(17) . . ?
O1 C11 C12 113.28(17) . . ?
C13 C12 C17 119.20(17) . . ?
C13 C12 C11 121.59(17) . . ?
C17 C12 C11 119.19(17) . . ?
C12 C13 C14 118.52(17) . . ?
C12 C13 S1 120.57(14) . . ?
C14 C13 S1 120.91(14) . . ?
C15 C14 C13 120.92(18) . . ?
C15 C14 H14 119.5 . . ?
C13 C14 H14 119.5 . . ?
C14 C15 C16 121.03(18) . . ?
C14 C15 H15 119.5 . . ?
C16 C15 H15 119.5 . . ?
C15 C16 C17 118.50(18) . . ?
C15 C16 H16 120.7 . . ?
C17 C16 H16 120.7 . . ?
C12 C17 C16 121.77(18) . . ?
C12 C17 H17 119.1 . . ?
C16 C17 H17 119.1 . . ?
C23 C18 C19 118.78(17) . . ?
C23 C18 S2 121.46(15) . . ?
C19 C18 S2 119.72(14) . . ?
C18 C19 C20 119.12(18) . . ?
C18 C19 C24 122.33(17) . . ?
C20 C19 C24 118.54(17) . . ?
C21 C20 C19 121.70(18) . . ?
C21 C20 H20 119.1 . . ?
C19 C20 H20 119.1 . . ?
C20 C21 C22 118.83(18) . . ?
C20 C21 H21 120.6 . . ?
C22 C21 H21 120.6 . . ?
C23 C22 C21 120.68(19) . . ?
C23 C22 H22 119.7 . . ?
C21 C22 H22 119.7 . . ?
C18 C23 C22 120.88(18) . . ?
C18 C23 H23 119.6 . . ?
C22 C23 H23 119.6 . . ?
O4 C24 O3 123.98(18) . . ?
O4 C24 C19 123.22(18) . . ?
O3 C24 C19 112.79(16) . . ?
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 C13 1.7980(19) . ?
S1 S2 2.0573(8) . ?
S2 C18 1.7986(19) . ?
O1 C11 1.316(2) . ?
O1 H1O 0.8401(11) . ?
O2 C11 1.219(2) . ?
O3 C24 1.318(2) . ?
O3 H3O 0.8401(11) . ?
O4 C24 1.212(2) . ?
N1 C5 1.339(3) . ?
N1 C1 1.335(3) . ?
N2 C9 1.338(3) . ?
N2 C8 1.336(3) . ?
C1 C2 1.381(3) . ?
C1 H1 0.9500 . ?
C2 C3 1.397(3) . ?
C2 H2 0.9500 . ?
C3 C4 1.389(3) . ?
C3 C6 1.490(3) . ?
C4 C5 1.383(3) . ?
C4 H4 0.9500 . ?
C5 H5 0.9500 . ?
C6 C7 1.393(3) . ?
C6 C10 1.391(3) . ?
C7 C8 1.384(3) . ?
C7 H7 0.9500 . ?
C8 H8 0.9500 . ?
C9 C10 1.378(3) . ?
C9 H9 0.9500 . ?
C10 H10 0.9500 . ?
C11 C12 1.488(3) . ?
C12 C13 1.407(3) . ?
C12 C17 1.396(3) . ?
C13 C14 1.396(3) . ?
C14 C15 1.381(3) . ?
C14 H14 0.9500 . ?
C15 C16 1.384(3) . ?
C15 H15 0.9500 . ?
C16 C17 1.382(3) . ?
C16 H16 0.9500 . ?
C17 H17 0.9500 . ?
C18 C23 1.393(3) . ?
C18 C19 1.406(3) . ?
C19 C20 1.394(3) . ?
C19 C24 1.486(3) . ?
C20 C21 1.382(3) . ?
C20 H20 0.9500 . ?
C21 C22 1.382(3) . ?
C21 H21 0.9500 . ?
C22 C23 1.385(3) . ?
C22 H22 0.9500 . ?
C23 H23 0.9500 . ?
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 21132241
2 PubChem 139065516
