#------------------------------------------------------------------------------
#$Date: 2017-10-13 14:42:48 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201982 $
#$URL: file:///home/coder/svn-repositories/cod/cif/4/50/51/4505189.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_4505189
loop_
_publ_author_name
'Succaw, Gary L.'
'Weakley, Timothy J. R.'
'Han, Fusan'
'Doxsee, Kenneth M.'
_publ_section_title
;
 Crystal Engineering with Bis(thiourea) Derivatives†
;
_journal_issue                   6
_journal_name_full               'Crystal Growth & Design'
_journal_page_first              2288
_journal_paper_doi               10.1021/cg050162c
_journal_volume                  5
_journal_year                    2005
_chemical_formula_moiety         'C12 H18 N4 S2 '
_chemical_formula_sum            'C12 H18 N4 S2'
_chemical_formula_weight         282.42
_space_group_IT_number           61
_symmetry_cell_setting           orthorhombic
_symmetry_Int_Tables_number      61
_symmetry_space_group_name_Hall  '-P 2ac 2ab'
_symmetry_space_group_name_H-M   'P b c a'
_audit_creation_date             2003-09-05
_audit_creation_method           'by teXsan v1.8'
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   14.741(2)
_cell_length_b                   9.1370(15)
_cell_length_c                   20.542(2)
_cell_measurement_reflns_used    25
_cell_measurement_temperature    296
_cell_measurement_theta_max      10.8
_cell_measurement_theta_min      9.6
_cell_volume                     2766.8(6)
_computing_cell_refinement       'CAD4/PC (Enraf-Nonius, 1993)'
_computing_data_collection       'CAD4/PC (Enraf-Nonius, 1993)'
_computing_data_reduction        'TEXSAN (Molecular Structure Corp., 1997)'
_computing_publication_material  'TEXSAN (Molecular Structure Corp., 1997)'
_computing_structure_refinement  'TEXSAN (Molecular Structure Corp., 1997)'
_computing_structure_solution    'TEXSAN (Molecular Structure Corp., 1997)'
_diffrn_ambient_temperature      296
_diffrn_measurement_device_type  'Nonius CAD-4 serial diffractometer'
_diffrn_measurement_method       ω-θ
_diffrn_orient_matrix_UB_11      -0.04438
_diffrn_orient_matrix_UB_12      -0.08266
_diffrn_orient_matrix_UB_13      -0.00234
_diffrn_orient_matrix_UB_21      0.01794
_diffrn_orient_matrix_UB_22      -0.01841
_diffrn_orient_matrix_UB_23      -0.04622
_diffrn_orient_matrix_UB_31      0.04806
_diffrn_orient_matrix_UB_32      -0.06932
_diffrn_orient_matrix_UB_33      0.01507
_diffrn_radiation_detector       'scintillation counter'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'sealed X-ray tube'
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.00000
_diffrn_reflns_av_sigmaI/netI    0.130
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_h_min       0
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       0
_diffrn_reflns_limit_l_max       0
_diffrn_reflns_limit_l_min       -24
_diffrn_reflns_number            2774
_diffrn_reflns_reduction_process 'Lp corrections applied'
_diffrn_reflns_theta_max         25.0
_diffrn_reflns_theta_min         1.7
_diffrn_standards_decay_%        0.00
_diffrn_standards_interval_count 300
_diffrn_standards_number         3
_exptl_absorpt_coefficient_mu    0.373
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.356
_exptl_crystal_density_meas      ?
_exptl_crystal_description       prism
_exptl_crystal_F_000             1200
_exptl_crystal_size_max          0.29
_exptl_crystal_size_mid          0.16
_exptl_crystal_size_min          0.12
_refine_diff_density_max         0.51
_refine_diff_density_min         -0.59
_refine_ls_abs_structure_details 'not applicable'
_refine_ls_extinction_coef       0.000000
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_all   1.08
_refine_ls_goodness_of_fit_ref   1.14
_refine_ls_hydrogen_treatment    refall
_refine_ls_matrix_type           full
_refine_ls_number_constraints    0
_refine_ls_number_parameters     235
_refine_ls_number_reflns         2420
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.072
_refine_ls_R_factor_gt           0.044
_refine_ls_shift/su_max          0.0010
_refine_ls_shift/su_mean         0.0000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     'w = 4Fₒ²/[σ²(I) + (0.025I)²]'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_all         0.093
_refine_ls_wR_factor_ref         0.042
_reflns_number_gt                1575
_reflns_number_total             2774
_reflns_threshold_expression     I>1.00σ(I)
_cod_data_source_file            cg050162csi20050909_024735.cif
_cod_data_source_block           GS0600
_cod_depositor_comments
;
The following automatic conversions were performed:

'_exptl_crystal_density_meas' value 'not measured' was changed to '?'
- the value is perceived as not measured.

Automatic conversion script
Id: cif_fix_values 3008 2015-01-20 13:52:24Z robertas 
;
_cod_original_cell_volume        2766.7(6)
_cod_original_sg_symbol_H-M      'P b c a    '
_cod_original_formula_sum        'C12 H18 N4 S2 '
_cod_database_code               4505189
loop_
_symmetry_equiv_pos_as_xyz
'   +x,   +y,   +z'
'1/2+x,1/2-y,   -z'
'   -x,1/2+y,1/2-z'
'1/2-x,   -y,1/2+z'
'   -x,   -y,   -z'
'1/2-x,1/2+y,   +z'
'   +x,1/2-y,1/2+z'
'1/2+x,   +y,1/2-z'
loop_
_atom_site_label
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_occupancy
_atom_site_adp_type
_atom_site_calc_flag
S(1) 0.61438(5) 0.71768(9) 0.33522(4) 0.0386(2) 1.000 Uani d
S(2) 0.49670(6) 0.07879(9) 0.36020(4) 0.0457(3) 1.000 Uani d
N(1) 0.6426(2) 0.4823(3) 0.26332(13) 0.0434(9) 1.000 Uani d
N(2) 0.73350(17) 0.4987(3) 0.35238(12) 0.0341(8) 1.000 Uani d
N(3) 0.44171(18) 0.3111(3) 0.42787(12) 0.0375(8) 1.000 Uani d
N(4) 0.4233(2) 0.3237(3) 0.31824(13) 0.0430(8) 1.000 Uani d
C(1) 0.6657(3) 0.3313(4) 0.2481(2) 0.0524(12) 1.000 Uani d
C(2) 0.6671(2) 0.5561(3) 0.31622(13) 0.0325(8) 1.000 Uani d
C(3) 0.7558(3) 0.5434(4) 0.41863(15) 0.0379(10) 1.000 Uani d
C(4) 0.7098(2) 0.4456(3) 0.46798(13) 0.0299(8) 1.000 Uani d
C(5) 0.7548(2) 0.3963(4) 0.52291(14) 0.0372(9) 1.000 Uani d
C(6) 0.7116(2) 0.3023(4) 0.56549(15) 0.0454(10) 1.000 Uani d
C(7) 0.6234(2) 0.2574(4) 0.55455(14) 0.0418(10) 1.000 Uani d
C(8) 0.5767(2) 0.3069(3) 0.50009(13) 0.0311(8) 1.000 Uani d
C(9) 0.6213(2) 0.4003(3) 0.45747(14) 0.0324(8) 1.000 Uani d
C(10) 0.4804(2) 0.2573(4) 0.48791(16) 0.0411(10) 1.000 Uani d
C(11) 0.45189(19) 0.2481(3) 0.36977(14) 0.0337(8) 1.000 Uani d
C(12) 0.3898(3) 0.4735(4) 0.3178(2) 0.0558(13) 1.000 Uani d
H(1) 0.627(2) 0.300(4) 0.2119(17) 0.077(10) 1.000 Uiso d
H(2) 0.726(3) 0.318(4) 0.2382(16) 0.067(10) 1.000 Uiso d
H(3) 0.650(3) 0.263(4) 0.2855(18) 0.087(10) 1.000 Uiso d
H(4) 0.6023(19) 0.518(3) 0.2405(14) 0.033(8) 1.000 Uiso d
H(5) 0.758(2) 0.426(3) 0.3385(14) 0.040(9) 1.000 Uiso d
H(6) 0.736(2) 0.648(4) 0.4228(13) 0.045(8) 1.000 Uiso d
H(7) 0.8158(19) 0.531(3) 0.4245(12) 0.024(7) 1.000 Uiso d
H(8) 0.814(2) 0.427(3) 0.5301(14) 0.044(9) 1.000 Uiso d
H(9) 0.7429(19) 0.272(3) 0.6038(13) 0.045(8) 1.000 Uiso d
H(10) 0.593(2) 0.186(4) 0.5852(15) 0.065(9) 1.000 Uiso d
H(11) 0.5914(18) 0.438(3) 0.4191(13) 0.036(8) 1.000 Uiso d
H(12) 0.442(2) 0.283(3) 0.5262(14) 0.050(8) 1.000 Uiso d
H(13) 0.4818(18) 0.153(3) 0.4866(12) 0.031(8) 1.000 Uiso d
H(14) 0.418(2) 0.392(3) 0.4294(14) 0.033(9) 1.000 Uiso d
H(15) 0.435(2) 0.284(4) 0.2826(15) 0.047(9) 1.000 Uiso d
H(16) 0.383(3) 0.511(4) 0.2724(19) 0.095(10) 1.000 Uiso d
H(17) 0.433(2) 0.535(4) 0.3392(16) 0.060(9) 1.000 Uiso d
H(18) 0.334(3) 0.484(4) 0.3392(18) 0.084(10) 1.000 Uiso d
loop_
_atom_type_symbol
_atom_type_oxidation_number
_atom_type_number_in_cell
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C 0 96 0.002 0.002
;International Tables for Crystallography
(1992, Vol. C, Tables 4.2.6.8 and 6.1.1.1)
;
H 0 144 0.000 0.000
;International Tables for Crystallography
(1992, Vol. C, Table 6.1.1.2)
;
N 0 32 0.004 0.003
;International Tables for Crystallography
(1992, Vol. C, Tables 4.2.6.8 and 6.1.1.1)
;
S 0 16 0.110 0.124
;International Tables for Crystallography
(1992, Vol. C, Tables 4.2.6.8 and 6.1.1.1)
;
loop_
_diffrn_standard_refln_index_h
_diffrn_standard_refln_index_k
_diffrn_standard_refln_index_l
0 0 10
0 0 -10
0 4 8
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_publ_flag
C(1) N(1) C(2) 126.4(3) yes
C(1) N(1) H(4) 115.1(21) no
C(2) N(1) H(4) 117.3(21) no
C(2) N(2) C(3) 125.0(3) yes
C(2) N(2) H(5) 117.1(22) no
C(3) N(2) H(5) 117.3(22) no
C(10) N(3) C(11) 124.9(3) yes
C(10) N(3) H(14) 116.3(21) no
C(11) N(3) H(14) 118.2(21) no
C(11) N(4) C(12) 126.9(3) yes
C(11) N(4) H(15) 113.8(22) no
C(12) N(4) H(15) 118.3(22) no
N(1) C(1) H(1) 107.7(22) no
N(1) C(1) H(2) 113.3(23) no
N(1) C(1) H(3) 111.7(22) no
H(1) C(1) H(2) 110.8(30) no
H(1) C(1) H(3) 105.2(30) no
H(2) C(1) H(3) 107.9(31) no
S(1) C(2) N(1) 120.0(2) yes
S(1) C(2) N(2) 123.0(2) yes
N(1) C(2) N(2) 117.0(3) yes
N(2) C(3) C(4) 111.0(3) yes
N(2) C(3) H(6) 106.3(16) no
N(2) C(3) H(7) 108.1(16) no
C(4) C(3) H(6) 112.1(16) no
C(4) C(3) H(7) 105.8(17) no
H(6) C(3) H(7) 113.6(24) no
C(3) C(4) C(5) 121.6(3) yes
C(3) C(4) C(9) 119.6(3) yes
C(5) C(4) C(9) 118.7(3) yes
C(4) C(5) C(6) 119.8(3) yes
C(4) C(5) H(8) 118.8(18) no
C(6) C(5) H(8) 121.3(18) no
C(5) C(6) C(7) 121.0(3) yes
C(5) C(6) H(9) 118.7(18) no
C(7) C(6) H(9) 120.2(18) no
C(6) C(7) C(8) 120.1(3) yes
C(6) C(7) H(10) 120.1(19) no
C(8) C(7) H(10) 119.8(19) no
C(7) C(8) C(9) 118.2(3) yes
C(7) C(8) C(10) 120.1(3) yes
C(9) C(8) C(10) 121.7(3) yes
C(4) C(9) C(8) 122.1(3) yes
C(4) C(9) H(11) 116.8(16) no
C(8) C(9) H(11) 121.1(16) no
N(3) C(10) C(8) 114.2(3) yes
N(3) C(10) H(12) 111.4(17) no
N(3) C(10) H(13) 108.9(16) no
C(8) C(10) H(12) 109.7(17) no
C(8) C(10) H(13) 106.5(17) no
H(12) C(10) H(13) 105.7(24) no
S(2) C(11) N(3) 122.8(3) yes
S(2) C(11) N(4) 120.3(2) yes
N(3) C(11) N(4) 116.8(3) yes
N(4) C(12) H(16) 111.6(23) no
N(4) C(12) H(17) 108.6(20) no
N(4) C(12) H(18) 113.1(26) no
H(16) C(12) H(17) 107.1(29) no
H(16) C(12) H(18) 108.0(32) no
H(17) C(12) H(18) 108.1(31) no
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_publ_flag
S(1) C(2) 1.713(3) yes
S(2) C(11) 1.694(3) yes
N(1) C(1) 1.455(4) yes
N(1) C(2) 1.329(4) yes
N(1) H(4) 0.83(3) no
N(2) C(2) 1.336(4) yes
N(2) C(3) 1.459(4) yes
N(2) H(5) 0.81(3) no
N(3) C(10) 1.445(4) yes
N(3) C(11) 1.334(4) yes
N(3) H(14) 0.82(3) no
N(4) C(11) 1.333(4) yes
N(4) C(12) 1.454(4) yes
N(4) H(15) 0.84(3) no
C(1) H(1) 0.98(4) no
C(1) H(2) 0.91(4) no
C(1) H(3) 1.02(4) no
C(3) C(4) 1.512(4) yes
C(3) H(6) 1.00(3) no
C(3) H(7) 0.90(3) no
C(4) C(5) 1.384(4) yes
C(4) C(9) 1.386(4) yes
C(5) C(6) 1.382(4) yes
C(5) H(8) 0.93(3) no
C(6) C(7) 1.382(4) yes
C(6) H(9) 0.95(3) no
C(7) C(8) 1.389(4) yes
C(7) H(10) 1.01(3) no
C(8) C(9) 1.388(4) yes
C(8) C(10) 1.510(4) yes
C(9) H(11) 0.97(3) no
C(10) H(12) 1.00(3) no
C(10) H(13) 0.95(3) no
C(12) H(16) 1.00(4) no
C(12) H(17) 0.96(3) no
C(12) H(18) 0.94(4) no
loop_
_geom_contact_atom_site_label_1
_geom_contact_atom_site_label_2
_geom_contact_distance
_geom_contact_site_symmetry_2
_geom_contact_publ_flag
S(1) N(4) 3.344(3) 3_655 no
S(1) N(2) 3.427(3) 6_655 no
S(2) N(1) 3.381(3) 3_645 no
N(1) N(4) 3.672(4) 3_655 no
N(3) C(5) 3.494(4) 2_456 no
N(3) C(6) 3.550(4) 2_456 no
N(3) C(9) 3.656(4) 5_666 no
C(1) C(12) 3.632(5) 3_645 no
C(5) C(10) 3.616(5) 2_556 no
C(6) C(12) 3.491(5) 5_666 no
C(7) C(12) 3.601(5) 5_666 no
C(9) C(10) 3.646(5) 5_666 no
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_publ_flag
S(1) C(2) N(1) C(1) -165.6(3) no
S(1) C(2) N(2) C(3) 14.9(4) no
S(2) C(11) N(3) C(10) 11.1(4) no
S(2) C(11) N(4) C(12) -175.0(3) no
N(1) C(2) N(2) C(3) -165.3(3) no
N(2) C(2) N(1) C(1) 14.7(5) no
N(2) C(3) C(4) C(5) 137.9(3) no
N(2) C(3) C(4) C(9) -40.4(4) no
N(3) C(10) C(8) C(7) -177.0(3) no
N(3) C(10) C(8) C(9) 2.1(4) no
N(3) C(11) N(4) C(12) 6.3(5) no
N(4) C(11) N(3) C(10) -170.2(3) no
C(2) N(2) C(3) C(4) 95.3(4) no
C(3) C(4) C(5) C(6) -177.4(3) no
C(3) C(4) C(9) C(8) 178.0(3) no
C(4) C(5) C(6) C(7) -0.7(5) no
C(4) C(9) C(8) C(7) -0.4(4) no
C(4) C(9) C(8) C(10) -179.5(3) no
C(5) C(4) C(9) C(8) -0.3(4) no
C(5) C(6) C(7) C(8) -0.0(5) no
C(6) C(5) C(4) C(9) 0.8(4) no
C(6) C(7) C(8) C(9) 0.6(4) no
C(6) C(7) C(8) C(10) 179.7(3) no
C(8) C(10) N(3) C(11) 85.2(4) no
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 4301935
