#------------------------------------------------------------------------------
#$Date: 2016-03-26 16:26:43 +0200 (Sat, 26 Mar 2016) $
#$Revision: 180339 $
#$URL: svn://www.crystallography.net/cod/cif/7/20/08/7200826.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_7200826
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         'C10 H13 N O S, 0.5(C12 H10 N2)'
_chemical_formula_sum            'C16 H18 N2 O S'
_chemical_formula_weight         286.39
_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                 95.738(11)
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   11.454(4)
_cell_length_b                   14.950(6)
_cell_length_c                   17.707(7)
_cell_measurement_reflns_used    9397
_cell_measurement_temperature    98(2)
_cell_measurement_theta_max      30.5
_cell_measurement_theta_min      1.8
_cell_volume                     3017(2)
_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    'SHELXS97 (Sheldrick, 1997)'
_diffrn_ambient_temperature      98(2)
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.997
_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  0.043
_diffrn_reflns_av_sigmaI/netI    0.032
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_number            13387
_diffrn_reflns_theta_full        25.0
_diffrn_reflns_theta_max         25.0
_diffrn_reflns_theta_min         2.3
_diffrn_standards_decay_%        '< 1'
_diffrn_standards_interval_count 0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.212
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.261
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             1216
_exptl_crystal_size_max          0.35
_exptl_crystal_size_mid          0.30
_exptl_crystal_size_min          0.30
_refine_diff_density_max         0.40
_refine_diff_density_min         -0.41
_refine_diff_density_rms         0.079
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.20
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     181
_refine_ls_number_reflns         2658
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.20
_refine_ls_R_factor_all          0.078
_refine_ls_R_factor_gt           0.072
_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)+(0.1181P)²+3.524P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.201
_refine_ls_wR_factor_ref         0.214
_reflns_number_gt                2496
_reflns_number_total             2658
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            b822555a.txt
_cod_data_source_block           5
_cod_original_sg_symbol_H-M      'C 2/c'
_cod_database_code               7200826
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 0.45389(6) 0.75096(4) 0.47674(4) 0.0367(3) Uani 1 1 d . . .
O1 O 0.28641(17) 0.63188(13) 0.43279(11) 0.0391(5) Uani 1 1 d . . .
N1 N 0.3807(2) 0.60880(14) 0.54661(13) 0.0332(6) Uani 1 1 d . . .
H1N H 0.4352 0.6245 0.5828 0.040 Uiso 1 1 calc R . .
N2 N 0.6023(2) 0.61951(16) 0.65296(14) 0.0407(6) Uani 1 1 d . . .
C1 C 0.3692(2) 0.66122(18) 0.48496(16) 0.0342(6) Uani 1 1 d . . .
C2 C 0.3148(2) 0.53061(17) 0.56047(15) 0.0331(6) Uani 1 1 d . . .
C3 C 0.1930(3) 0.52920(19) 0.54888(18) 0.0408(7) Uani 1 1 d . . .
H3 H 0.1510 0.5801 0.5289 0.049 Uiso 1 1 calc R . .
C4 C 0.1336(3) 0.45288(19) 0.56681(17) 0.0404(7) Uani 1 1 d . . .
H4 H 0.0504 0.4518 0.5589 0.048 Uiso 1 1 calc R . .
C5 C 0.1930(3) 0.37796(19) 0.59603(16) 0.0379(7) Uani 1 1 d . . .
H5 H 0.1512 0.3258 0.6079 0.046 Uiso 1 1 calc R . .
C6 C 0.3140(3) 0.38018(19) 0.60771(16) 0.0364(7) Uani 1 1 d . . .
H6 H 0.3558 0.3291 0.6276 0.044 Uiso 1 1 calc R . .
C7 C 0.3749(2) 0.45663(18) 0.59062(15) 0.0337(6) Uani 1 1 d . . .
H7 H 0.4581 0.4581 0.5997 0.040 Uiso 1 1 calc R . .
C8 C 0.2587(3) 0.6825(2) 0.36215(16) 0.0435(7) Uani 1 1 d . . .
H8 H 0.2641 0.7480 0.3732 0.052 Uiso 1 1 calc R . .
C9 C 0.3449(3) 0.6579(3) 0.30596(19) 0.0564(9) Uani 1 1 d . . .
H9A H 0.4240 0.6765 0.3260 0.085 Uiso 1 1 calc R . .
H9B H 0.3228 0.6883 0.2576 0.085 Uiso 1 1 calc R . .
H9C H 0.3436 0.5930 0.2980 0.085 Uiso 1 1 calc R . .
C10 C 0.1338(3) 0.6583(3) 0.3352(2) 0.0574(9) Uani 1 1 d . . .
H10A H 0.0821 0.6772 0.3731 0.086 Uiso 1 1 calc R . .
H10B H 0.1275 0.5934 0.3280 0.086 Uiso 1 1 calc R . .
H10C H 0.1104 0.6885 0.2870 0.086 Uiso 1 1 calc R . .
C11 C 0.6469(3) 0.6061(3) 0.72474(19) 0.0652(12) Uani 1 1 d . . .
H11 H 0.5937 0.5985 0.7621 0.078 Uiso 1 1 calc R . .
C12 C 0.7649(3) 0.6026(3) 0.74796(18) 0.0585(10) Uani 1 1 d . . .
H12 H 0.7910 0.5925 0.7999 0.070 Uiso 1 1 calc R . .
C13 C 0.8460(2) 0.61363(16) 0.69551(15) 0.0313(6) Uani 1 1 d . . .
C14 C 0.8005(2) 0.6268(2) 0.62057(16) 0.0361(7) Uani 1 1 d . . .
H14 H 0.8518 0.6341 0.5820 0.043 Uiso 1 1 calc R . .
C15 C 0.6802(2) 0.62927(19) 0.60237(16) 0.0359(7) Uani 1 1 d . . .
H15 H 0.6514 0.6385 0.5508 0.043 Uiso 1 1 calc R . .
C16 C 0.9734(2) 0.61271(17) 0.71509(16) 0.0333(6) Uani 1 1 d . . .
H16 H 1.0215 0.6121 0.6744 0.040 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 120.0(2) . . ?
C1 N1 C2 127.6(2) . . ?
C1 N1 H1N 116.2 . . ?
C2 N1 H1N 116.2 . . ?
C15 N2 C11 115.9(3) . . ?
O1 C1 N1 112.2(2) . . ?
O1 C1 S1 125.7(2) . . ?
N1 C1 S1 122.0(2) . . ?
C7 C2 C3 119.9(3) . . ?
C7 C2 N1 118.1(2) . . ?
C3 C2 N1 121.8(2) . . ?
C4 C3 C2 119.2(3) . . ?
C4 C3 H3 120.4 . . ?
C2 C3 H3 120.4 . . ?
C3 C4 C5 121.3(3) . . ?
C3 C4 H4 119.3 . . ?
C5 C4 H4 119.3 . . ?
C6 C5 C4 119.0(3) . . ?
C6 C5 H5 120.5 . . ?
C4 C5 H5 120.5 . . ?
C5 C6 C7 120.4(3) . . ?
C5 C6 H6 119.8 . . ?
C7 C6 H6 119.8 . . ?
C2 C7 C6 120.1(3) . . ?
C2 C7 H7 119.9 . . ?
C6 C7 H7 119.9 . . ?
O1 C8 C10 105.3(3) . . ?
O1 C8 C9 109.6(3) . . ?
C10 C8 C9 113.2(3) . . ?
O1 C8 H8 109.5 . . ?
C10 C8 H8 109.5 . . ?
C9 C8 H8 109.5 . . ?
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 . . ?
C8 C10 H10A 109.5 . . ?
C8 C10 H10B 109.5 . . ?
H10A C10 H10B 109.5 . . ?
C8 C10 H10C 109.5 . . ?
H10A C10 H10C 109.5 . . ?
H10B C10 H10C 109.5 . . ?
N2 C11 C12 124.2(3) . . ?
N2 C11 H11 117.9 . . ?
C12 C11 H11 117.9 . . ?
C11 C12 C13 120.0(3) . . ?
C11 C12 H12 120.0 . . ?
C13 C12 H12 120.0 . . ?
C12 C13 C14 116.3(3) . . ?
C12 C13 C16 123.9(3) . . ?
C14 C13 C16 119.8(2) . . ?
C15 C14 C13 119.7(2) . . ?
C15 C14 H14 120.1 . . ?
C13 C14 H14 120.1 . . ?
N2 C15 C14 123.9(3) . . ?
N2 C15 H15 118.0 . . ?
C14 C15 H15 118.0 . . ?
C16 C16 C13 125.2(3) 2_756 . ?
C16 C16 H16 117.4 2_756 . ?
C13 C16 H16 117.4 . . ?
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 1.671(3) . ?
O1 C1 1.330(3) . ?
O1 C8 1.469(4) . ?
N1 C1 1.339(4) . ?
N1 C2 1.426(3) . ?
N1 H1N 0.8800 . ?
N2 C15 1.335(4) . ?
N2 C11 1.337(4) . ?
C2 C7 1.381(4) . ?
C2 C3 1.391(4) . ?
C3 C4 1.381(4) . ?
C3 H3 0.9500 . ?
C4 C5 1.384(4) . ?
C4 H4 0.9500 . ?
C5 C6 1.381(4) . ?
C5 H5 0.9500 . ?
C6 C7 1.388(4) . ?
C6 H6 0.9500 . ?
C7 H7 0.9500 . ?
C8 C10 1.507(4) . ?
C8 C9 1.515(4) . ?
C8 H8 1.0000 . ?
C9 H9A 0.9800 . ?
C9 H9B 0.9800 . ?
C9 H9C 0.9800 . ?
C10 H10A 0.9800 . ?
C10 H10B 0.9800 . ?
C10 H10C 0.9800 . ?
C11 C12 1.374(5) . ?
C11 H11 0.9500 . ?
C12 C13 1.388(4) . ?
C12 H12 0.9500 . ?
C13 C14 1.390(4) . ?
C13 C16 1.465(4) . ?
C14 C15 1.384(4) . ?
C14 H14 0.9500 . ?
C15 H15 0.9500 . ?
C16 C16 1.323(6) 2_756 ?
C16 H16 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 178.1(2) . . . . ?
C8 O1 C1 S1 -3.4(3) . . . . ?
C2 N1 C1 O1 -1.1(4) . . . . ?
C2 N1 C1 S1 -179.7(2) . . . . ?
C1 N1 C2 C7 135.7(3) . . . . ?
C1 N1 C2 C3 -48.3(4) . . . . ?
C7 C2 C3 C4 -0.9(4) . . . . ?
N1 C2 C3 C4 -176.9(3) . . . . ?
C2 C3 C4 C5 0.0(5) . . . . ?
C3 C4 C5 C6 0.3(4) . . . . ?
C4 C5 C6 C7 0.3(4) . . . . ?
C3 C2 C7 C6 1.5(4) . . . . ?
N1 C2 C7 C6 177.6(2) . . . . ?
C5 C6 C7 C2 -1.2(4) . . . . ?
C1 O1 C8 C10 -154.8(3) . . . . ?
C1 O1 C8 C9 83.1(3) . . . . ?
C15 N2 C11 C12 0.4(6) . . . . ?
N2 C11 C12 C13 0.3(7) . . . . ?
C11 C12 C13 C14 -0.8(5) . . . . ?
C11 C12 C13 C16 178.7(3) . . . . ?
C12 C13 C14 C15 0.7(4) . . . . ?
C16 C13 C14 C15 -178.9(2) . . . . ?
C11 N2 C15 C14 -0.5(5) . . . . ?
C13 C14 C15 N2 -0.1(4) . . . . ?
C12 C13 C16 C16 -9.0(4) . . . 2_756 ?
C14 C13 C16 C16 170.53(18) . . . 2_756 ?
