#------------------------------------------------------------------------------
#$Date: 2016-03-26 16:26:43 +0200 (Sat, 26 Mar 2016) $
#$Revision: 180339 $
#$URL: svn://www.crystallography.net/cod/cif/7/20/08/7200824.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_7200824
loop_
_publ_author_name
'Ellis, Carol A.'
'Miller, Michael A.'
'Spencer, James'
'Zukerman-Schpector, Julio'
'Tiekink, Edward R. T.'
_publ_section_title
;
 Co-crystallization experiments of thiocarbamides with bipyridine-type
 molecules
;
_journal_issue                   7
_journal_name_full               CrystEngComm
_journal_page_first              1352
_journal_paper_doi               10.1039/b822555a
_journal_volume                  11
_journal_year                    2009
_chemical_formula_moiety         'C12 H10 N2, 2(C9 H11 N O S)'
_chemical_formula_sum            'C30 H32 N4 O2 S2'
_chemical_formula_weight         544.72
_chemical_name_systematic
;
?
;
_space_group_IT_number           2
_symmetry_cell_setting           triclinic
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                98.324(7)
_cell_angle_beta                 110.766(5)
_cell_angle_gamma                91.310(2)
_cell_formula_units_Z            1
_cell_length_a                   8.0156(17)
_cell_length_b                   9.3410(17)
_cell_length_c                   9.916(3)
_cell_measurement_reflns_used    1417
_cell_measurement_temperature    120(2)
_cell_measurement_theta_max      30.1
_cell_measurement_theta_min      2.7
_cell_volume                     684.7(3)
_computing_cell_refinement       CrystalClear
_computing_data_collection       'CrystalClear (Rigaku, 2005)'
_computing_data_reduction        CrystalClear
_computing_molecular_graphics    'ORTEPII (Johnson, 1976)'
_computing_publication_material  SHELXL97
_computing_structure_refinement  'SHELXL97 (Sheldrick, 1997)'
_computing_structure_solution    'SIR-92 (Altomare et al., 1994)'
_diffrn_ambient_temperature      120(2)
_diffrn_measured_fraction_theta_full 0.995
_diffrn_measured_fraction_theta_max 0.995
_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  0.024
_diffrn_reflns_av_sigmaI/netI    0.026
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            7075
_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    0.230
_exptl_absorpt_correction_T_max  1
_exptl_absorpt_correction_T_min  0.913
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'ABSCOR (Higashi, 1995)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.321
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             288
_exptl_crystal_size_max          0.35
_exptl_crystal_size_mid          0.30
_exptl_crystal_size_min          0.15
_refine_diff_density_max         0.29
_refine_diff_density_min         -0.27
_refine_diff_density_rms         0.048
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.05
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     172
_refine_ls_number_reflns         2810
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.05
_refine_ls_R_factor_all          0.046
_refine_ls_R_factor_gt           0.043
_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)+(0.0594P)²+0.2824P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.111
_refine_ls_wR_factor_ref         0.115
_reflns_number_gt                2625
_reflns_number_total             2810
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            b822555a.txt
_cod_data_source_block           shelxl3
_cod_database_code               7200824
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'
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 0.33095(6) 0.66931(4) 0.68643(4) 0.03339(15) Uani 1 1 d . . .
O1 O 0.34482(15) 0.40446(12) 0.55227(12) 0.0296(3) Uani 1 1 d . . .
N1 N 0.54365(17) 0.46298(14) 0.77869(13) 0.0274(3) Uani 1 1 d . . .
H1N H 0.5968 0.5309 0.8548 0.033 Uiso 1 1 calc R . .
N2 N 0.74042(18) 0.68024(14) 1.05189(14) 0.0315(3) Uani 1 1 d . . .
C1 C 0.4083(2) 0.50596(16) 0.67085(16) 0.0261(3) Uani 1 1 d . . .
C2 C 0.6148(2) 0.32521(16) 0.78959(16) 0.0258(3) Uani 1 1 d . . .
C3 C 0.5997(2) 0.21771(17) 0.67179(17) 0.0298(3) Uani 1 1 d . . .
H3 H 0.5393 0.2340 0.5745 0.036 Uiso 1 1 calc R . .
C4 C 0.6735(2) 0.08643(18) 0.69756(18) 0.0337(4) Uani 1 1 d . . .
H4 H 0.6614 0.0126 0.6172 0.040 Uiso 1 1 calc R . .
C5 C 0.7644(2) 0.06181(18) 0.83871(19) 0.0353(4) Uani 1 1 d . . .
H5 H 0.8144 -0.0281 0.8553 0.042 Uiso 1 1 calc R . .
C6 C 0.7812(2) 0.16961(18) 0.95503(18) 0.0349(4) Uani 1 1 d . . .
H6 H 0.8443 0.1538 1.0520 0.042 Uiso 1 1 calc R . .
C7 C 0.7070(2) 0.30076(17) 0.93157(17) 0.0303(3) Uani 1 1 d . . .
H7 H 0.7191 0.3740 1.0124 0.036 Uiso 1 1 calc R . .
C8 C 0.2021(2) 0.43604(17) 0.42439(17) 0.0300(3) Uani 1 1 d . . .
H8A H 0.2382 0.5227 0.3913 0.036 Uiso 1 1 calc R . .
H8B H 0.0927 0.4545 0.4466 0.036 Uiso 1 1 calc R . .
C9 C 0.1686(2) 0.30400(18) 0.30851(18) 0.0347(4) Uani 1 1 d . . .
H9A H 0.0727 0.3198 0.2190 0.052 Uiso 1 1 calc R . .
H9B H 0.1332 0.2193 0.3430 0.052 Uiso 1 1 calc R . .
H9C H 0.2782 0.2870 0.2882 0.052 Uiso 1 1 calc R . .
C10 C 0.8717(2) 0.65593(18) 1.17380(18) 0.0336(4) Uani 1 1 d . . .
H10 H 0.9224 0.5651 1.1714 0.040 Uiso 1 1 calc R . .
C11 C 0.9376(2) 0.75424(17) 1.30206(17) 0.0300(3) Uani 1 1 d . . .
H11 H 1.0307 0.7306 1.3846 0.036 Uiso 1 1 calc R . .
C12 C 0.8661(2) 0.88904(16) 1.30950(16) 0.0257(3) Uani 1 1 d . . .
C13 C 0.7303(2) 0.91505(17) 1.18376(17) 0.0299(3) Uani 1 1 d . . .
H13 H 0.6766 1.0047 1.1832 0.036 Uiso 1 1 calc R . .
C14 C 0.6734(2) 0.81026(17) 1.05940(17) 0.0317(4) Uani 1 1 d . . .
H14 H 0.5819 0.8316 0.9746 0.038 Uiso 1 1 calc R . .
C15 C 0.9283(2) 1.00159(16) 1.43969(16) 0.0275(3) Uani 1 1 d . . .
H15 H 0.8609 1.0841 1.4383 0.033 Uiso 1 1 calc R . .
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
C1 O1 C8 119.26(12) . . ?
C1 N1 C2 130.32(13) . . ?
C1 N1 H1N 114.8 . . ?
C2 N1 H1N 114.8 . . ?
C14 N2 C10 115.99(13) . . ?
O1 C1 N1 112.58(13) . . ?
O1 C1 S1 124.54(11) . . ?
N1 C1 S1 122.88(11) . . ?
C7 C2 C3 119.48(14) . . ?
C7 C2 N1 115.23(13) . . ?
C3 C2 N1 125.29(13) . . ?
C2 C3 C4 119.57(14) . . ?
C2 C3 H3 120.2 . . ?
C4 C3 H3 120.2 . . ?
C5 C4 C3 120.95(15) . . ?
C5 C4 H4 119.5 . . ?
C3 C4 H4 119.5 . . ?
C4 C5 C6 119.21(15) . . ?
C4 C5 H5 120.4 . . ?
C6 C5 H5 120.4 . . ?
C7 C6 C5 120.67(15) . . ?
C7 C6 H6 119.7 . . ?
C5 C6 H6 119.7 . . ?
C2 C7 C6 120.10(15) . . ?
C2 C7 H7 120.0 . . ?
C6 C7 H7 120.0 . . ?
O1 C8 C9 106.10(12) . . ?
O1 C8 H8A 110.5 . . ?
C9 C8 H8A 110.5 . . ?
O1 C8 H8B 110.5 . . ?
C9 C8 H8B 110.5 . . ?
H8A C8 H8B 108.7 . . ?
C8 C9 H9A 109.5 . . ?
C8 C9 H9B 109.5 . . ?
H9A C9 H9B 109.5 . . ?
C8 C9 H9C 109.5 . . ?
H9A C9 H9C 109.5 . . ?
H9B C9 H9C 109.5 . . ?
N2 C10 C11 124.29(15) . . ?
N2 C10 H10 117.9 . . ?
C11 C10 H10 117.9 . . ?
C12 C11 C10 119.41(15) . . ?
C12 C11 H11 120.3 . . ?
C10 C11 H11 120.3 . . ?
C11 C12 C13 116.63(14) . . ?
C11 C12 C15 123.64(14) . . ?
C13 C12 C15 119.72(14) . . ?
C14 C13 C12 119.99(14) . . ?
C14 C13 H13 120.0 . . ?
C12 C13 H13 120.0 . . ?
N2 C14 C13 123.68(14) . . ?
N2 C14 H14 118.2 . . ?
C13 C14 H14 118.2 . . ?
C15 C15 C12 125.73(18) 2_778 . ?
C15 C15 H15 117.1 2_778 . ?
C12 C15 H15 117.1 . . ?
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 C1 1.6672(16) . ?
O1 C1 1.3309(18) . ?
O1 C8 1.4490(18) . ?
N1 C1 1.343(2) . ?
N1 C2 1.4225(19) . ?
N1 H1N 0.8800 . ?
N2 C14 1.342(2) . ?
N2 C10 1.345(2) . ?
C2 C7 1.394(2) . ?
C2 C3 1.393(2) . ?
C3 C4 1.391(2) . ?
C3 H3 0.9500 . ?
C4 C5 1.386(2) . ?
C4 H4 0.9500 . ?
C5 C6 1.382(2) . ?
C5 H5 0.9500 . ?
C6 C7 1.388(2) . ?
C6 H6 0.9500 . ?
C7 H7 0.9500 . ?
C8 C9 1.507(2) . ?
C8 H8A 0.9900 . ?
C8 H8B 0.9900 . ?
C9 H9A 0.9800 . ?
C9 H9B 0.9800 . ?
C9 H9C 0.9800 . ?
C10 C11 1.380(2) . ?
C10 H10 0.9500 . ?
C11 C12 1.399(2) . ?
C11 H11 0.9500 . ?
C12 C13 1.391(2) . ?
C12 C15 1.465(2) . ?
C13 C14 1.385(2) . ?
C13 H13 0.9500 . ?
C14 H14 0.9500 . ?
C15 C15 1.338(3) 2_778 ?
C15 H15 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
C8 O1 C1 N1 -178.01(13) . . . . ?
C8 O1 C1 S1 1.9(2) . . . . ?
C2 N1 C1 O1 -6.7(2) . . . . ?
C2 N1 C1 S1 173.39(12) . . . . ?
C1 N1 C2 C7 -157.24(16) . . . . ?
C1 N1 C2 C3 23.2(3) . . . . ?
C7 C2 C3 C4 1.3(2) . . . . ?
N1 C2 C3 C4 -179.08(14) . . . . ?
C2 C3 C4 C5 -1.0(3) . . . . ?
C3 C4 C5 C6 0.1(3) . . . . ?
C4 C5 C6 C7 0.6(3) . . . . ?
C3 C2 C7 C6 -0.7(2) . . . . ?
N1 C2 C7 C6 179.65(15) . . . . ?
C5 C6 C7 C2 -0.2(3) . . . . ?
C1 O1 C8 C9 176.95(13) . . . . ?
C14 N2 C10 C11 0.5(3) . . . . ?
N2 C10 C11 C12 0.0(3) . . . . ?
C10 C11 C12 C13 -0.1(2) . . . . ?
C10 C11 C12 C15 -179.11(15) . . . . ?
C11 C12 C13 C14 -0.4(2) . . . . ?
C15 C12 C13 C14 178.66(15) . . . . ?
C10 N2 C14 C13 -1.1(2) . . . . ?
C12 C13 C14 N2 1.0(3) . . . . ?
C11 C12 C15 C15 8.1(3) . . . 2_778 ?
C13 C12 C15 C15 -170.9(2) . . . 2_778 ?
