#------------------------------------------------------------------------------
#$Date: 2017-10-14 22:27:35 +0300 (Sat, 14 Oct 2017) $
#$Revision: 202017 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/20/29/7202971.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_7202971
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 H20 N2 O4 S2'
_chemical_formula_sum            'C26 H20 N2 O4 S2'
_chemical_formula_weight         488.56
_chemical_name_systematic
;
?
;
_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                 90.323(1)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   10.6070(2)
_cell_length_b                   12.3972(2)
_cell_length_c                   17.3834(4)
_cell_measurement_reflns_used    5450
_cell_measurement_temperature    120(2)
_cell_measurement_theta_max      27.5
_cell_measurement_theta_min      1.0
_cell_volume                     2285.83(8)
_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  0.042
_diffrn_reflns_av_sigmaI/netI    0.034
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_number            28252
_diffrn_reflns_theta_full        26.5
_diffrn_reflns_theta_max         26.5
_diffrn_reflns_theta_min         1.9
_diffrn_standards_decay_%        0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.270
_exptl_absorpt_correction_T_max  1
_exptl_absorpt_correction_T_min  0.893
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS V2.10 (Sheldrick, 2003)'
_exptl_crystal_colour            light-tan
_exptl_crystal_density_diffrn    1.420
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             1016
_exptl_crystal_size_max          0.48
_exptl_crystal_size_mid          0.40
_exptl_crystal_size_min          0.16
_refine_diff_density_max         0.31
_refine_diff_density_min         -0.45
_refine_diff_density_rms         0.071
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.09
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     313
_refine_ls_number_reflns         4740
_refine_ls_number_restraints     2
_refine_ls_restrained_S_all      1.08
_refine_ls_R_factor_all          0.056
_refine_ls_R_factor_gt           0.037
_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)+(0.0684P)²+0.4034P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.097
_refine_ls_wR_factor_ref         0.115
_reflns_number_gt                3710
_reflns_number_total             4740
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            b707690h.txt
_cod_data_source_block
(HO2C)C6H4SSC6H4(CO2H).{1,2-bis(pyridine)ethene}(2)
_cod_original_sg_symbol_H-M      P21/c
_cod_database_code               7202971
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 0.21830(4) 0.29155(4) 0.39495(3) 0.02451(14) Uani 1 1 d . . .
S2 S 0.38056(4) 0.33541(4) 0.33878(3) 0.02332(14) Uani 1 1 d . . .
O1 O -0.10525(12) 0.34508(11) 0.54855(8) 0.0278(3) Uani 1 1 d D . .
H1O H -0.1696(13) 0.3071(15) 0.5405(13) 0.042 Uiso 1 1 d D . .
O2 O -0.01134(12) 0.24622(11) 0.45761(8) 0.0305(3) Uani 1 1 d . . .
O3 O 0.62141(12) 0.52928(12) 0.18393(9) 0.0357(4) Uani 1 1 d D . .
H3O H 0.6950(9) 0.5052(19) 0.1789(14) 0.054 Uiso 1 1 d D . .
O4 O 0.59455(11) 0.38962(10) 0.26406(7) 0.0237(3) Uani 1 1 d . . .
N1 N -0.32285(14) 0.24750(13) 0.54013(9) 0.0257(4) Uani 1 1 d . . .
N2 N -1.15047(14) 0.03841(13) 0.65754(9) 0.0274(4) Uani 1 1 d . . .
C1 C -0.37462(19) 0.18065(17) 0.48859(12) 0.0308(5) Uani 1 1 d . . .
H1 H -0.3259 0.1595 0.4455 0.037 Uiso 1 1 calc R . .
C2 C -0.49595(18) 0.14077(16) 0.49512(11) 0.0285(4) Uani 1 1 d . . .
H2 H -0.5293 0.0942 0.4567 0.034 Uiso 1 1 calc R . .
C3 C -0.56861(17) 0.16914(14) 0.55802(10) 0.0213(4) Uani 1 1 d . . .
C4 C -0.51410(17) 0.23852(16) 0.61167(11) 0.0270(4) Uani 1 1 d . . .
H4 H -0.5600 0.2601 0.6559 0.032 Uiso 1 1 calc R . .
C5 C -0.39323(18) 0.27568(16) 0.60031(11) 0.0279(4) Uani 1 1 d . . .
H5 H -0.3582 0.3238 0.6372 0.034 Uiso 1 1 calc R . .
C6 C -0.69670(17) 0.12482(15) 0.56678(11) 0.0237(4) Uani 1 1 d . . .
H6 H -0.7220 0.0693 0.5324 0.028 Uiso 1 1 calc R . .
C7 C -0.77861(17) 0.15648(14) 0.61874(11) 0.0226(4) Uani 1 1 d . . .
H7 H -0.7525 0.2127 0.6524 0.027 Uiso 1 1 calc R . .
C8 C -0.90631(16) 0.11355(14) 0.62991(10) 0.0212(4) Uani 1 1 d . . .
C9 C -0.98821(18) 0.16819(15) 0.67838(12) 0.0290(5) Uani 1 1 d . . .
H9 H -0.9615 0.2324 0.7034 0.035 Uiso 1 1 calc R . .
C10 C -1.10820(18) 0.12901(16) 0.69005(12) 0.0308(5) Uani 1 1 d . . .
H10 H -1.1632 0.1683 0.7227 0.037 Uiso 1 1 calc R . .
C11 C -1.07189(17) -0.01561(15) 0.61156(11) 0.0253(4) Uani 1 1 d . . .
H11 H -1.1006 -0.0806 0.5885 0.030 Uiso 1 1 calc R . .
C12 C -0.95062(17) 0.01897(15) 0.59608(10) 0.0230(4) Uani 1 1 d . . .
H12 H -0.8981 -0.0215 0.5627 0.028 Uiso 1 1 calc R . .
C13 C -0.00897(17) 0.31706(14) 0.50611(11) 0.0211(4) Uani 1 1 d . . .
C14 C 0.10680(16) 0.38088(14) 0.52442(10) 0.0205(4) Uani 1 1 d . . .
C15 C 0.21582(16) 0.37595(14) 0.47889(10) 0.0209(4) Uani 1 1 d . . .
C16 C 0.32033(17) 0.43743(16) 0.50037(11) 0.0274(4) Uani 1 1 d . . .
H16 H 0.3939 0.4359 0.4695 0.033 Uiso 1 1 calc R . .
C17 C 0.31859(18) 0.50044(17) 0.56584(12) 0.0308(5) Uani 1 1 d . . .
H17 H 0.3913 0.5408 0.5799 0.037 Uiso 1 1 calc R . .
C18 C 0.21224(18) 0.50530(16) 0.61100(11) 0.0289(4) Uani 1 1 d . . .
H18 H 0.2112 0.5486 0.6561 0.035 Uiso 1 1 calc R . .
C19 C 0.10747(17) 0.44637(15) 0.58976(11) 0.0245(4) Uani 1 1 d . . .
H19 H 0.0337 0.4504 0.6204 0.029 Uiso 1 1 calc R . .
C20 C 0.33664(16) 0.45691(14) 0.28932(10) 0.0185(4) Uani 1 1 d . . .
C21 C 0.42445(16) 0.51194(14) 0.24340(10) 0.0185(4) Uani 1 1 d . . .
C22 C 0.38779(17) 0.60633(15) 0.20581(10) 0.0225(4) Uani 1 1 d . . .
H22 H 0.4480 0.6449 0.1764 0.027 Uiso 1 1 calc R . .
C23 C 0.26560(18) 0.64522(15) 0.21039(11) 0.0248(4) Uani 1 1 d . . .
H23 H 0.2413 0.7083 0.1831 0.030 Uiso 1 1 calc R . .
C24 C 0.17988(17) 0.59060(15) 0.25543(11) 0.0241(4) Uani 1 1 d . . .
H24 H 0.0958 0.6165 0.2592 0.029 Uiso 1 1 calc R . .
C25 C 0.21508(17) 0.49876(15) 0.29501(10) 0.0222(4) Uani 1 1 d . . .
H25 H 0.1553 0.4634 0.3267 0.027 Uiso 1 1 calc R . .
C26 C 0.55524(17) 0.47048(14) 0.23216(10) 0.0213(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
C15 S1 S2 104.35(6) . . ?
C20 S2 S1 103.51(6) . . ?
C13 O1 H1O 113.1(16) . . ?
C26 O3 H3O 111.6(18) . . ?
C1 N1 C5 117.27(16) . . ?
C10 N2 C11 117.75(17) . . ?
N1 C1 C2 123.05(19) . . ?
N1 C1 H1 118.5 . . ?
C2 C1 H1 118.5 . . ?
C3 C2 C1 119.70(18) . . ?
C3 C2 H2 120.2 . . ?
C1 C2 H2 120.2 . . ?
C4 C3 C2 117.02(17) . . ?
C4 C3 C6 122.73(17) . . ?
C2 C3 C6 120.24(17) . . ?
C3 C4 C5 119.60(18) . . ?
C3 C4 H4 120.2 . . ?
C5 C4 H4 120.2 . . ?
N1 C5 C4 123.35(18) . . ?
N1 C5 H5 118.3 . . ?
C4 C5 H5 118.3 . . ?
C7 C6 C3 124.88(18) . . ?
C7 C6 H6 117.6 . . ?
C3 C6 H6 117.6 . . ?
C6 C7 C8 126.52(18) . . ?
C6 C7 H7 116.7 . . ?
C8 C7 H7 116.7 . . ?
C9 C8 C12 117.11(17) . . ?
C9 C8 C7 118.91(17) . . ?
C12 C8 C7 123.95(17) . . ?
C8 C9 C10 119.89(18) . . ?
C8 C9 H9 120.1 . . ?
C10 C9 H9 120.1 . . ?
N2 C10 C9 122.88(19) . . ?
N2 C10 H10 118.6 . . ?
C9 C10 H10 118.6 . . ?
N2 C11 C12 122.97(18) . . ?
N2 C11 H11 118.5 . . ?
C12 C11 H11 118.5 . . ?
C11 C12 C8 119.39(17) . . ?
C11 C12 H12 120.3 . . ?
C8 C12 H12 120.3 . . ?
O2 C13 O1 124.62(17) . . ?
O2 C13 C14 122.92(17) . . ?
O1 C13 C14 112.46(16) . . ?
C19 C14 C15 118.87(16) . . ?
C19 C14 C13 118.80(16) . . ?
C15 C14 C13 122.32(16) . . ?
C16 C15 C14 118.72(17) . . ?
C16 C15 S1 121.38(14) . . ?
C14 C15 S1 119.90(13) . . ?
C17 C16 C15 121.05(18) . . ?
C17 C16 H16 119.5 . . ?
C15 C16 H16 119.5 . . ?
C16 C17 C18 120.57(18) . . ?
C16 C17 H17 119.7 . . ?
C18 C17 H17 119.7 . . ?
C19 C18 C17 119.02(18) . . ?
C19 C18 H18 120.5 . . ?
C17 C18 H18 120.5 . . ?
C14 C19 C18 121.76(18) . . ?
C14 C19 H19 119.1 . . ?
C18 C19 H19 119.1 . . ?
C25 C20 C21 118.39(16) . . ?
C25 C20 S2 121.07(14) . . ?
C21 C20 S2 120.54(13) . . ?
C22 C21 C20 119.29(16) . . ?
C22 C21 C26 118.96(16) . . ?
C20 C21 C26 121.73(16) . . ?
C21 C22 C23 121.56(17) . . ?
C21 C22 H22 119.2 . . ?
C23 C22 H22 119.2 . . ?
C24 C23 C22 118.76(17) . . ?
C24 C23 H23 120.6 . . ?
C22 C23 H23 120.6 . . ?
C23 C24 C25 120.66(17) . . ?
C23 C24 H24 119.7 . . ?
C25 C24 H24 119.7 . . ?
C20 C25 C24 121.28(17) . . ?
C20 C25 H25 119.4 . . ?
C24 C25 H25 119.4 . . ?
O4 C26 O3 124.28(17) . . ?
O4 C26 C21 122.66(16) . . ?
O3 C26 C21 113.06(15) . . ?
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 1.7958(18) . ?
S1 S2 2.0567(6) . ?
S2 C20 1.7946(18) . ?
O1 C13 1.310(2) . ?
O1 H1O 0.8400(10) . ?
O2 C13 1.218(2) . ?
O3 C26 1.317(2) . ?
O3 H3O 0.8402(10) . ?
O4 C26 1.218(2) . ?
N1 C1 1.336(2) . ?
N1 C5 1.335(2) . ?
N2 C10 1.334(3) . ?
N2 C11 1.338(2) . ?
C1 C2 1.384(3) . ?
C1 H1 0.9500 . ?
C2 C3 1.387(3) . ?
C2 H2 0.9500 . ?
C3 C4 1.392(3) . ?
C3 C6 1.474(2) . ?
C4 C5 1.378(3) . ?
C4 H4 0.9500 . ?
C5 H5 0.9500 . ?
C6 C7 1.317(3) . ?
C6 H6 0.9500 . ?
C7 C8 1.469(2) . ?
C7 H7 0.9500 . ?
C8 C9 1.390(3) . ?
C8 C12 1.392(3) . ?
C9 C10 1.378(3) . ?
C9 H9 0.9500 . ?
C10 H10 0.9500 . ?
C11 C12 1.384(3) . ?
C11 H11 0.9500 . ?
C12 H12 0.9500 . ?
C13 C14 1.494(2) . ?
C14 C19 1.396(3) . ?
C14 C15 1.406(2) . ?
C15 C16 1.394(2) . ?
C16 C17 1.381(3) . ?
C16 H16 0.9500 . ?
C17 C18 1.379(3) . ?
C17 H17 0.9500 . ?
C18 C19 1.379(3) . ?
C18 H18 0.9500 . ?
C19 H19 0.9500 . ?
C20 C25 1.394(2) . ?
C20 C21 1.407(2) . ?
C21 C22 1.395(3) . ?
C21 C26 1.493(2) . ?
C22 C23 1.386(3) . ?
C22 H22 0.9500 . ?
C23 C24 1.381(3) . ?
C23 H23 0.9500 . ?
C24 C25 1.381(3) . ?
C24 H24 0.9500 . ?
C25 H25 0.9500 . ?
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 30653662
