#------------------------------------------------------------------------------
#$Date: 2016-03-26 16:52:31 +0200 (Sat, 26 Mar 2016) $
#$Revision: 180360 $
#$URL: svn://www.crystallography.net/cod/cif/7/20/29/7202976.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_7202976
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         'C20 H16 N O4 S2'
_chemical_formula_sum            'C20 H16 N O4 S2'
_chemical_formula_weight         398.46
_chemical_name_systematic
;
?
;
_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                 100.80(3)
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   19.734(4)
_cell_length_b                   7.8916(16)
_cell_length_c                   23.226(5)
_cell_measurement_reflns_used    7576
_cell_measurement_temperature    173(2)
_cell_measurement_theta_max      30.7
_cell_measurement_theta_min      3.
_cell_volume                     3553.0(13)
_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 0.994
_diffrn_measured_fraction_theta_max 0.994
_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  0.031
_diffrn_reflns_av_sigmaI/netI    0.028
_diffrn_reflns_limit_h_max       25
_diffrn_reflns_limit_h_min       -25
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       25
_diffrn_reflns_limit_l_min       -30
_diffrn_reflns_number            12762
_diffrn_reflns_theta_full        27.5
_diffrn_reflns_theta_max         27.5
_diffrn_reflns_theta_min         3.2
_diffrn_standards_decay_%        '< 1'
_diffrn_standards_interval_count 0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.327
_exptl_absorpt_correction_T_max  1
_exptl_absorpt_correction_T_min  0.833
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'ABSCOR (Higashi, 1995)'
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.490
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             1656
_exptl_crystal_size_max          0.39
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.08
_refine_diff_density_max         0.31
_refine_diff_density_min         -0.22
_refine_diff_density_rms         0.049
_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     253
_refine_ls_number_reflns         4046
_refine_ls_number_restraints     3
_refine_ls_restrained_S_all      1.09
_refine_ls_R_factor_all          0.041
_refine_ls_R_factor_gt           0.040
_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)+(0.0347P)²+4.5253P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.093
_refine_ls_wR_factor_ref         0.094
_reflns_number_gt                3863
_reflns_number_total             4046
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            b707690h.txt
_cod_data_source_block
'[(HO2C)C6H4SSC6H4(CO2)].[1,2-bis(pyridineH)ethane]0.5(7)'
_cod_original_sg_symbol_H-M      C2/c
_cod_database_code               7202976
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 0.41225(2) 0.50108(5) -0.123251(18) 0.02653(11) Uani 1 1 d . . .
S2 S 0.38983(2) 0.54004(5) -0.041615(17) 0.02616(11) Uani 1 1 d . . .
O1 O 0.44730(7) 0.44633(18) -0.22832(6) 0.0390(3) Uani 1 1 d D . .
H1O H 0.4839(16) 0.435(6) -0.241(2) 0.059 Uiso 0.50 1 d PD . .
O2 O 0.40570(7) 0.23534(19) -0.28713(6) 0.0423(3) Uani 1 1 d . . .
O3 O 0.34991(7) 0.84954(17) 0.10676(5) 0.0364(3) Uani 1 1 d D . .
H3O H 0.3677(11) 0.808(3) 0.1394(5) 0.055 Uiso 1 1 d D . .
O4 O 0.38667(8) 0.61087(17) 0.07140(6) 0.0403(3) Uani 1 1 d . . .
N1 N 0.50985(8) -0.1718(2) -0.19121(6) 0.0314(3) Uani 1 1 d D . .
H1N H 0.512(2) -0.183(5) -0.2285(5) 0.047 Uiso 0.50 1 d PD . .
C1 C 0.47901(11) -0.0351(2) -0.17431(8) 0.0384(4) Uani 1 1 d . . .
H1 H 0.4551 0.0390 -0.2034 0.046 Uiso 1 1 calc R . .
C2 C 0.48057(10) 0.0026(2) -0.11587(8) 0.0352(4) Uani 1 1 d . . .
H2 H 0.4581 0.1011 -0.1053 0.042 Uiso 1 1 calc R . .
C3 C 0.51524(8) -0.1045(2) -0.07286(7) 0.0253(3) Uani 1 1 d . . .
C4 C 0.54874(9) -0.2434(2) -0.09173(7) 0.0275(3) Uani 1 1 d . . .
H4 H 0.5747 -0.3173 -0.0637 0.033 Uiso 1 1 calc R . .
C5 C 0.54464(9) -0.2748(2) -0.15029(8) 0.0290(4) Uani 1 1 d . . .
H5 H 0.5670 -0.3719 -0.1621 0.035 Uiso 1 1 calc R . .
C6 C 0.51710(9) -0.0804(2) -0.00820(7) 0.0265(3) Uani 1 1 d . . .
H6A H 0.5659 -0.0803 0.0122 0.032 Uiso 1 1 calc R . .
H6B H 0.4943 -0.1788 0.0065 0.032 Uiso 1 1 calc R . .
C7 C 0.40063(9) 0.3386(2) -0.24827(7) 0.0265(3) Uani 1 1 d . . .
C8 C 0.33721(8) 0.3418(2) -0.22133(7) 0.0230(3) Uani 1 1 d . . .
C9 C 0.33520(8) 0.41503(19) -0.16642(7) 0.0217(3) Uani 1 1 d . . .
C10 C 0.27262(9) 0.4213(2) -0.14706(7) 0.0259(3) Uani 1 1 d . . .
H10 H 0.2707 0.4721 -0.1103 0.031 Uiso 1 1 calc R . .
C11 C 0.21301(9) 0.3545(2) -0.18053(8) 0.0293(4) Uani 1 1 d . . .
H11 H 0.1706 0.3616 -0.1669 0.035 Uiso 1 1 calc R . .
C12 C 0.21516(9) 0.2777(2) -0.23372(8) 0.0316(4) Uani 1 1 d . . .
H12 H 0.1746 0.2297 -0.2564 0.038 Uiso 1 1 calc R . .
C13 C 0.27711(9) 0.2716(2) -0.25341(7) 0.0294(4) Uani 1 1 d . . .
H13 H 0.2787 0.2182 -0.2898 0.035 Uiso 1 1 calc R . .
C14 C 0.34773(8) 0.7423(2) -0.04631(7) 0.0230(3) Uani 1 1 d . . .
C15 C 0.33581(8) 0.8237(2) 0.00482(7) 0.0232(3) Uani 1 1 d . . .
C16 C 0.30209(9) 0.9801(2) -0.00008(8) 0.0302(4) Uani 1 1 d . . .
H16 H 0.2943 1.0357 0.0344 0.036 Uiso 1 1 calc R . .
C17 C 0.27979(10) 1.0558(2) -0.05387(9) 0.0359(4) Uani 1 1 d . . .
H17 H 0.2561 1.1612 -0.0565 0.043 Uiso 1 1 calc R . .
C18 C 0.29236(10) 0.9764(2) -0.10383(8) 0.0350(4) Uani 1 1 d . . .
H18 H 0.2779 1.0282 -0.1410 0.042 Uiso 1 1 calc R . .
C19 C 0.32592(9) 0.8220(2) -0.10000(7) 0.0290(4) Uani 1 1 d . . .
H19 H 0.3343 0.7692 -0.1348 0.035 Uiso 1 1 calc R . .
C20 C 0.36019(8) 0.7490(2) 0.06359(7) 0.0257(3) 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
C9 S1 S2 105.49(6) . . ?
C14 S2 S1 104.78(6) . . ?
C7 O1 H1O 114(3) . . ?
C20 O3 H3O 110.7(17) . . ?
C1 N1 C5 118.93(15) . . ?
C1 N1 H1N 119(3) . . ?
C5 N1 H1N 122(3) . . ?
N1 C1 C2 122.37(17) . . ?
N1 C1 H1 118.8 . . ?
C2 C1 H1 118.8 . . ?
C1 C2 C3 119.48(17) . . ?
C1 C2 H2 120.3 . . ?
C3 C2 H2 120.3 . . ?
C2 C3 C4 116.89(16) . . ?
C2 C3 C6 123.88(15) . . ?
C4 C3 C6 119.22(15) . . ?
C5 C4 C3 120.76(16) . . ?
C5 C4 H4 119.6 . . ?
C3 C4 H4 119.6 . . ?
N1 C5 C4 121.50(16) . . ?
N1 C5 H5 119.2 . . ?
C4 C5 H5 119.2 . . ?
C3 C6 C6 115.20(18) . 5_655 ?
C3 C6 H6A 108.5 . . ?
C6 C6 H6A 108.5 5_655 . ?
C3 C6 H6B 108.5 . . ?
C6 C6 H6B 108.5 5_655 . ?
H6A C6 H6B 107.5 . . ?
O2 C7 O1 123.66(16) . . ?
O2 C7 C8 120.29(16) . . ?
O1 C7 C8 116.05(14) . . ?
C13 C8 C9 118.86(15) . . ?
C13 C8 C7 117.61(14) . . ?
C9 C8 C7 123.51(15) . . ?
C10 C9 C8 118.98(15) . . ?
C10 C9 S1 121.15(12) . . ?
C8 C9 S1 119.86(12) . . ?
C11 C10 C9 121.08(15) . . ?
C11 C10 H10 119.5 . . ?
C9 C10 H10 119.5 . . ?
C12 C11 C10 120.14(16) . . ?
C12 C11 H11 119.9 . . ?
C10 C11 H11 119.9 . . ?
C13 C12 C11 119.14(16) . . ?
C13 C12 H12 120.4 . . ?
C11 C12 H12 120.4 . . ?
C12 C13 C8 121.74(16) . . ?
C12 C13 H13 119.1 . . ?
C8 C13 H13 119.1 . . ?
C19 C14 C15 118.53(15) . . ?
C19 C14 S2 121.26(13) . . ?
C15 C14 S2 120.21(12) . . ?
C16 C15 C14 119.11(15) . . ?
C16 C15 C20 119.61(15) . . ?
C14 C15 C20 121.26(14) . . ?
C17 C16 C15 121.49(16) . . ?
C17 C16 H16 119.3 . . ?
C15 C16 H16 119.3 . . ?
C16 C17 C18 119.14(17) . . ?
C16 C17 H17 120.4 . . ?
C18 C17 H17 120.4 . . ?
C17 C18 C19 120.35(17) . . ?
C17 C18 H18 119.8 . . ?
C19 C18 H18 119.8 . . ?
C18 C19 C14 121.37(16) . . ?
C18 C19 H19 119.3 . . ?
C14 C19 H19 119.3 . . ?
O4 C20 O3 123.42(16) . . ?
O4 C20 C15 123.64(15) . . ?
O3 C20 C15 112.94(14) . . ?
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 C9 1.7909(17) . ?
S1 S2 2.0494(7) . ?
S2 C14 1.7935(16) . ?
O1 C7 1.275(2) . ?
O1 H1O 0.8400(11) . ?
O2 C7 1.234(2) . ?
O3 C20 1.324(2) . ?
O3 H3O 0.8400(11) . ?
O4 C20 1.208(2) . ?
N1 C1 1.333(2) . ?
N1 C5 1.338(2) . ?
N1 H1N 0.8800(11) . ?
C1 C2 1.384(3) . ?
C1 H1 0.9500 . ?
C2 C3 1.387(2) . ?
C2 H2 0.9500 . ?
C3 C4 1.393(2) . ?
C3 C6 1.507(2) . ?
C4 C5 1.370(2) . ?
C4 H4 0.9500 . ?
C5 H5 0.9500 . ?
C6 C6 1.519(3) 5_655 ?
C6 H6A 0.9900 . ?
C6 H6B 0.9900 . ?
C7 C8 1.501(2) . ?
C8 C13 1.392(2) . ?
C8 C9 1.407(2) . ?
C9 C10 1.392(2) . ?
C10 C11 1.387(2) . ?
C10 H10 0.9500 . ?
C11 C12 1.384(2) . ?
C11 H11 0.9500 . ?
C12 C13 1.384(2) . ?
C12 H12 0.9500 . ?
C13 H13 0.9500 . ?
C14 C19 1.391(2) . ?
C14 C15 1.408(2) . ?
C15 C16 1.397(2) . ?
C15 C20 1.482(2) . ?
C16 C17 1.380(3) . ?
C16 H16 0.9500 . ?
C17 C18 1.382(3) . ?
C17 H17 0.9500 . ?
C18 C19 1.381(3) . ?
C18 H18 0.9500 . ?
C19 H19 0.9500 . ?
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
C9 S1 S2 C14 -83.86(8) . . . . ?
C5 N1 C1 C2 -1.2(3) . . . . ?
N1 C1 C2 C3 0.0(3) . . . . ?
C1 C2 C3 C4 1.9(3) . . . . ?
C1 C2 C3 C6 -176.72(18) . . . . ?
C2 C3 C4 C5 -2.7(2) . . . . ?
C6 C3 C4 C5 176.05(15) . . . . ?
C1 N1 C5 C4 0.5(3) . . . . ?
C3 C4 C5 N1 1.5(3) . . . . ?
C2 C3 C6 C6 -5.0(3) . . . 5_655 ?
C4 C3 C6 C6 176.36(17) . . . 5_655 ?
O2 C7 C8 C13 -21.8(2) . . . . ?
O1 C7 C8 C13 158.61(16) . . . . ?
O2 C7 C8 C9 159.73(16) . . . . ?
O1 C7 C8 C9 -19.9(2) . . . . ?
C13 C8 C9 C10 -2.6(2) . . . . ?
C7 C8 C9 C10 175.82(15) . . . . ?
C13 C8 C9 S1 178.29(12) . . . . ?
C7 C8 C9 S1 -3.2(2) . . . . ?
S2 S1 C9 C10 13.86(14) . . . . ?
S2 S1 C9 C8 -167.10(11) . . . . ?
C8 C9 C10 C11 1.0(2) . . . . ?
S1 C9 C10 C11 -179.98(13) . . . . ?
C9 C10 C11 C12 1.0(3) . . . . ?
C10 C11 C12 C13 -1.3(3) . . . . ?
C11 C12 C13 C8 -0.5(3) . . . . ?
C9 C8 C13 C12 2.4(3) . . . . ?
C7 C8 C13 C12 -176.13(16) . . . . ?
S1 S2 C14 C19 11.53(15) . . . . ?
S1 S2 C14 C15 -168.77(11) . . . . ?
C19 C14 C15 C16 0.6(2) . . . . ?
S2 C14 C15 C16 -179.14(12) . . . . ?
C19 C14 C15 C20 -177.56(15) . . . . ?
S2 C14 C15 C20 2.7(2) . . . . ?
C14 C15 C16 C17 0.5(3) . . . . ?
C20 C15 C16 C17 178.68(17) . . . . ?
C15 C16 C17 C18 -1.3(3) . . . . ?
C16 C17 C18 C19 0.9(3) . . . . ?
C17 C18 C19 C14 0.1(3) . . . . ?
C15 C14 C19 C18 -0.9(3) . . . . ?
S2 C14 C19 C18 178.81(14) . . . . ?
C16 C15 C20 O4 176.24(17) . . . . ?
C14 C15 C20 O4 -5.6(3) . . . . ?
C16 C15 C20 O3 -3.8(2) . . . . ?
C14 C15 C20 O3 174.35(15) . . . . ?
