#------------------------------------------------------------------------------
#$Date: 2016-02-16 22:30:59 +0200 (Tue, 16 Feb 2016) $
#$Revision: 176467 $
#$URL: svn://www.crystallography.net/cod/cif/4/50/51/4505192.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_4505192
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         'C15 H24 N4 S2 '
_chemical_formula_sum            'C15 H24 N4 S2'
_chemical_formula_weight         324.50
_space_group_IT_number           15
_symmetry_cell_setting           monoclinic
_symmetry_Int_Tables_number      15
_symmetry_space_group_name_Hall  '-C 2yc'
_symmetry_space_group_name_H-M   'C 1 2/c 1'
_audit_creation_date             2001-05-14
_audit_creation_method           'by teXsan v1.7'
_cell_angle_alpha                90
_cell_angle_beta                 107.38(1)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   23.056(2)
_cell_length_b                   8.6042(9)
_cell_length_c                   9.450(1)
_cell_measurement_reflns_used    25
_cell_measurement_temperature    296
_cell_measurement_theta_max      13.5
_cell_measurement_theta_min      12.5
_cell_volume                     1789.1(3)
_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  'Enraf-Nonius CAD-4 diffractometer'
_diffrn_measurement_method       ω
_diffrn_orient_matrix_UB_11      0.03164
_diffrn_orient_matrix_UB_12      0.07391
_diffrn_orient_matrix_UB_13      0.05834
_diffrn_orient_matrix_UB_21      -0.03223
_diffrn_orient_matrix_UB_22      0.07916
_diffrn_orient_matrix_UB_23      -0.00430
_diffrn_orient_matrix_UB_31      -0.00508
_diffrn_orient_matrix_UB_32      -0.04217
_diffrn_orient_matrix_UB_33      0.09420
_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  0.013
_diffrn_reflns_av_sigmaI/netI    0.060
_diffrn_reflns_limit_h_max       26
_diffrn_reflns_limit_h_min       -27
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       0
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_limit_l_min       0
_diffrn_reflns_number            1801
_diffrn_reflns_reduction_process 'Lp corrections applied'
_diffrn_reflns_theta_max         25.0
_diffrn_reflns_theta_min         1.9
_diffrn_standards_decay_%        0.00
_diffrn_standards_interval_time  60300
_diffrn_standards_number         3
_exptl_absorpt_coefficient_mu    0.297
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.205
_exptl_crystal_density_meas      ?
_exptl_crystal_description       tallet
_exptl_crystal_F_000             696.00
_exptl_crystal_size_max          0.27
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.05
_refine_diff_density_max         0.42
_refine_diff_density_min         -0.36
_refine_ls_abs_structure_details 'not applicable'
_refine_ls_extinction_coef       zero
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_all   3.24
_refine_ls_goodness_of_fit_ref   3.52
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_constraints    48
_refine_ls_number_parameters     97
_refine_ls_number_reflns         1567
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.089
_refine_ls_R_factor_gt           0.062
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.0010
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     'w = 4Fₒ²/[σ²(I) + (0.020I)²]'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_all         0.178
_refine_ls_wR_factor_ref         0.088
_reflns_number_gt                1190
_reflns_number_total             1567
_reflns_threshold_expression     I>1.00σ(I)
_cod_data_source_file            cg050162csi20050909_024735.cif
_cod_data_source_block           GS0501C
_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        1789.0(4)
_cod_original_sg_symbol_H-M      'C 2/c      '
_cod_original_formula_sum        'C15 H24 N4 S2 '
_cod_database_code               4505192
loop_
_symmetry_equiv_pos_as_xyz
'   +x,   +y,   +z'
'1/2+x,1/2+y,   +z'
'   -x,   +y,1/2-z'
1/2-x,1/2+y,1/2-z
'   -x,   -y,   -z'
'1/2-x,1/2-y,   -z'
'   +x,   -y,1/2+z'
1/2+x,1/2-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_refinement_flags
_atom_site_adp_type
_atom_site_calc_flag
S 0.65559(5) 0.2079(2) 0.4537(1) 0.0529(4) 1.000 . Uani d
N(1) 0.6462(1) 0.0608(5) 0.6947(4) 0.050(1) 1.000 . Uani d
N(2) 0.7408(1) 0.1428(5) 0.7033(4) 0.053(1) 1.000 . Uani d
C(1) 0.5000 0.535(1) 0.7500 0.107(4) 0.500 ST Uani d
C(2) 0.5000 0.3617(9) 0.7500 0.069(2) 0.500 ST Uani d
C(3) 0.5398(2) 0.2770(6) 0.6930(6) 0.061(2) 1.000 . Uani d
C(4) 0.5401(2) 0.1174(5) 0.6932(5) 0.046(1) 1.000 . Uani d
C(5) 0.5000 0.0386(7) 0.7500 0.044(2) 0.500 ST Uani d
C(6) 0.5816(2) 0.0275(6) 0.6249(5) 0.054(1) 1.000 . Uani d
C(7) 0.6821(2) 0.1323(5) 0.6268(5) 0.043(1) 1.000 . Uani d
C(8) 0.7698(2) 0.0857(7) 0.8511(6) 0.070(2) 1.000 . Uani d
C(9) 0.8333(3) 0.1423(8) 0.9132(8) 0.112(3) 1.000 . Uani d
H(1) 0.4772 0.5717 0.6548 0.131 0.500 . Uiso d
H(2) 0.5406 0.5717 0.7730 0.131 0.500 . Uiso d
H(3) 0.4822 0.5716 0.8222 0.131 1.000 . Uiso c
H(4) 0.5673 0.3312 0.6531 0.074 1.000 . Uiso c
H(5) 0.5000 -0.0718 0.7500 0.053 0.500 S Uiso d
H(6) 0.5750 -0.0805 0.6348 0.065 1.000 . Uiso c
H(7) 0.5715 0.0536 0.5227 0.065 1.000 . Uiso c
H(8) 0.6638 0.0297 0.7948 0.059 1.000 . Uiso c
H(9) 0.7663 0.1934 0.6552 0.064 1.000 . Uiso c
H(10) 0.7469 0.1193 0.9141 0.085 1.000 . Uiso c
H(11) 0.7702 -0.0246 0.8485 0.085 1.000 . Uiso c
H(12) 0.8601 0.0746 0.8833 0.134 1.000 . Uiso c
H(13) 0.8439 0.1440 1.0184 0.134 1.000 . Uiso c
H(14) 0.8365 0.2441 0.8775 0.134 1.000 . Uiso c
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 60 0.002 0.002
;International Tables for Crystallography
(1992, Vol. C, Tables 4.2.6.8 and 6.1.1.1)
;
H 0 96 0.000 0.000
;International Tables for Crystallography
(1992, Vol. C, Table 6.1.1.2)
;
N 0 16 0.004 0.003
;International Tables for Crystallography
(1992, Vol. C, Tables 4.2.6.8 and 6.1.1.1)
;
S 0 8 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
-1 5 -2
1 -5 2
-1 -5 -2
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
C(6) N(1) C(7) 124.4(4) . . yes
C(6) N(1) H(8) 117.8 . . no
C(7) N(1) H(8) 117.8 . . no
C(7) N(2) C(8) 127.1(4) . . yes
C(7) N(2) H(9) 116.4 . . no
C(8) N(2) H(9) 116.4 . . no
C(2) C(1) H(1) 109.5 . . no
C(2) C(1) H(1) 109.5 . 2_656 no
C(2) C(1) H(2) 109.5 . . no
C(2) C(1) H(2) 109.5 . 2_656 no
C(2) C(1) H(3) 109.5 . . no
C(2) C(1) H(3) 109.5 . 2_656 no
H(1) C(1) H(1) 141.0 . 2_656 no
H(1) C(1) H(2) 109.4 . . no
H(1) C(1) H(2) 56.2 . 2_656 no
H(1) C(1) H(3) 109.5 . . no
H(1) C(1) H(3) 56.2 . 2_656 no
H(1) C(1) H(2) 56.2 2_656 . no
H(1) C(1) H(2) 109.4 2_656 2_656 no
H(1) C(1) H(3) 56.2 2_656 . no
H(1) C(1) H(3) 109.5 2_656 2_656 no
H(2) C(1) H(2) 141.0 . 2_656 no
H(2) C(1) H(3) 109.4 . . no
H(2) C(1) H(3) 56.2 . 2_656 no
H(2) C(1) H(3) 56.2 2_656 . no
H(2) C(1) H(3) 109.4 2_656 2_656 no
H(3) C(1) H(3) 141.0 . 2_656 no
C(1) C(2) C(3) 121.4(3) . . yes
C(1) C(2) C(3) 121.4(3) . 2_656 yes
C(3) C(2) C(3) 117.2(7) . 2_656 yes
C(2) C(3) C(4) 121.5(5) . . yes
C(2) C(3) H(4) 119.2 . . no
C(4) C(3) H(4) 119.2 . . no
C(3) C(4) C(5) 119.3(5) . . yes
C(3) C(4) C(6) 120.8(4) . . yes
C(5) C(4) C(6) 119.8(4) . . yes
C(4) C(5) C(4) 121.1(6) . 2_656 yes
C(4) C(5) H(5) 119.5 . . no
C(4) C(5) H(5) 119.5 2_656 . no
N(1) C(6) C(4) 113.2(4) . . yes
N(1) C(6) H(6) 108.5 . . no
N(1) C(6) H(7) 108.5 . . no
C(4) C(6) H(6) 108.5 . . no
C(4) C(6) H(7) 108.5 . . no
H(6) C(6) H(7) 109.5 . . no
S C(7) N(1) 122.9(3) . . yes
S C(7) N(2) 120.8(3) . . yes
N(1) C(7) N(2) 116.3(4) . . yes
N(2) C(8) C(9) 112.8(4) . . yes
N(2) C(8) H(10) 108.6 . . no
N(2) C(8) H(11) 108.7 . . no
C(9) C(8) H(10) 108.6 . . no
C(9) C(8) H(11) 108.7 . . no
H(10) C(8) H(11) 109.4 . . no
C(8) C(9) H(12) 109.5 . . no
C(8) C(9) H(13) 109.5 . . no
C(8) C(9) H(14) 109.5 . . no
H(12) C(9) H(13) 109.4 . . no
H(12) C(9) H(14) 109.5 . . no
H(13) C(9) H(14) 109.5 . . no
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
S C(7) 1.696(4) . yes
N(1) C(6) 1.466(5) . yes
N(1) C(7) 1.338(5) . yes
N(1) H(8) 0.95 . no
N(2) C(7) 1.333(5) . yes
N(2) C(8) 1.443(6) . yes
N(2) H(9) 0.95 . no
C(1) C(2) 1.49(1) . yes
C(1) H(1) 0.95 . no
C(1) H(1) 0.95 2_656 no
C(1) H(2) 0.95 . no
C(1) H(2) 0.95 2_656 no
C(1) H(3) 0.95 . no
C(1) H(3) 0.95 2_656 no
C(2) C(3) 1.400(6) . yes
C(2) C(3) 1.400(6) 2_656 yes
C(3) C(4) 1.373(6) . yes
C(3) H(4) 0.95 . no
C(4) C(5) 1.378(5) . yes
C(4) C(6) 1.517(6) . yes
C(5) H(5) 0.95 . no
C(6) H(6) 0.95 . no
C(6) H(7) 0.95 . no
C(8) C(9) 1.488(7) . yes
C(8) H(10) 0.95 . no
C(8) H(11) 0.95 . no
C(9) H(12) 0.95 . no
C(9) H(13) 0.95 . no
C(9) H(14) 0.95 . 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 N(1) 3.326(4) 4_554 no
S N(2) 3.418(4) 7_656 no
C(5) C(6) 3.526(5) 3_656 no
C(5) C(6) 3.526(5) 4 no
