#------------------------------------------------------------------------------
#$Date: 2016-02-16 22:30:59 +0200 (Tue, 16 Feb 2016) $
#$Revision: 176467 $
#$URL: svn://www.crystallography.net/cod/cif/4/50/51/4505190.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_4505190
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         'C16 H26 N4 S2 '
_chemical_formula_sum            'C16 H26 N4 S2'
_chemical_formula_weight         338.53
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_Int_Tables_number      14
_symmetry_space_group_name_Hall  '-P 2yab'
_symmetry_space_group_name_H-M   'P 1 21/a 1'
_audit_creation_date             2002-11-22
_audit_creation_method           'by teXsan v1.8'
_cell_angle_alpha                90
_cell_angle_beta                 96.51(2)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   8.834(4)
_cell_length_b                   12.4201(18)
_cell_length_c                   17.0105(17)
_cell_measurement_reflns_used    25
_cell_measurement_temperature    296
_cell_measurement_theta_max      11.1
_cell_measurement_theta_min      7.7
_cell_volume                     1854.3(9)
_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  'NoniusCAD-4 serial diffractometer'
_diffrn_measurement_method       ω-2θ
_diffrn_orient_matrix_UB_11      0.01651
_diffrn_orient_matrix_UB_12      0.07833
_diffrn_orient_matrix_UB_13      0.01167
_diffrn_orient_matrix_UB_21      0.00724
_diffrn_orient_matrix_UB_22      -0.01551
_diffrn_orient_matrix_UB_23      0.05797
_diffrn_orient_matrix_UB_31      0.11250
_diffrn_orient_matrix_UB_32      -0.01042
_diffrn_orient_matrix_UB_33      0.00134
_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  0.0425
_diffrn_reflns_av_sigmaI/netI    0.140
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       0
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       0
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            2921
_diffrn_reflns_reduction_process 'Lp corrections applied'
_diffrn_reflns_theta_max         23.0
_diffrn_reflns_theta_min         1.6
_diffrn_standards_decay_%        4.0
_diffrn_standards_interval_time  60
_diffrn_standards_number         3
_exptl_absorpt_coefficient_mu    0.289
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.212
_exptl_crystal_density_meas      ?
_exptl_crystal_description       plate
_exptl_crystal_F_000             728.00
_exptl_crystal_size_max          0.47
_exptl_crystal_size_mid          0.22
_exptl_crystal_size_min          0.04
_refine_diff_density_max         0.70
_refine_diff_density_min         -0.62
_refine_ls_abs_structure_details 'not applicable'
_refine_ls_extinction_coef       0.00000
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_all   1.58
_refine_ls_goodness_of_fit_ref   1.93
_refine_ls_hydrogen_treatment    noref
_refine_ls_matrix_type           full
_refine_ls_number_constraints    0
_refine_ls_number_parameters     197
_refine_ls_number_reflns         2571
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.138
_refine_ls_R_factor_gt           0.078
_refine_ls_shift/su_max          0.0420
_refine_ls_shift/su_mean         0.0030
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     'w = 4F`o`²/[σ²(I) + (0.025I)²]'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_all         0.156
_refine_ls_wR_factor_ref         0.074
_reflns_number_gt                1636
_reflns_number_total             2728
_reflns_threshold_expression     I>1.00σ(I)
_cod_data_source_file            cg050162csi20050909_024735.cif
_cod_data_source_block           GS1102B
_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        1854.4(6)
_cod_original_sg_symbol_H-M      'P 21/a     '
_cod_original_formula_sum        'C16 H26 N4 S2 '
_cod_database_code               4505190
loop_
_symmetry_equiv_pos_as_xyz
'   +x,   +y,   +z'
'1/2-x,1/2+y,   -z'
'   -x,   -y,   -z'
'1/2+x,1/2-y,   +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) 0.0998(2) 0.08406(14) 0.62896(10) 0.0474(6) 1.000 Uani d
S(2) 0.1866(2) 0.42339(16) 0.14813(10) 0.0530(6) 1.000 Uani d
N(1) 0.3528(6) 0.1267(4) 0.7211(3) 0.0446(17) 1.000 Uani d
N(2) 0.3150(5) 0.2299(4) 0.6087(3) 0.0394(17) 1.000 Uani d
N(3) 0.4217(6) 0.3709(4) 0.2491(3) 0.0411(17) 1.000 Uani d
N(4) 0.3532(6) 0.2451(4) 0.1526(3) 0.0538(19) 1.000 Uani d
C(1) 0.4592(13) 0.2228(9) 0.8873(6) 0.132(5) 1.000 Uani d
C(2) 0.4945(11) 0.2600(9) 0.8083(6) 0.113(4) 1.000 Uani d
C(3) 0.5009(9) 0.1723(6) 0.7497(4) 0.061(3) 1.000 Uani d
C(4) 0.2681(7) 0.1523(5) 0.6540(4) 0.038(2) 1.000 Uani d
C(5) 0.2458(7) 0.2594(5) 0.5298(4) 0.043(2) 1.000 Uani d
C(6) 0.3252(7) 0.2093(5) 0.4656(3) 0.036(2) 1.000 Uani d
C(7) 0.3375(8) 0.0993(5) 0.4588(4) 0.048(2) 1.000 Uani d
C(8) 0.4136(9) 0.0547(5) 0.4003(4) 0.061(3) 1.000 Uani d
C(9) 0.4772(8) 0.1214(6) 0.3471(4) 0.054(3) 1.000 Uani d
C(10) 0.4656(7) 0.2315(5) 0.3523(3) 0.036(2) 1.000 Uani d
C(11) 0.3883(7) 0.2732(5) 0.4122(3) 0.0353(19) 1.000 Uani d
C(12) 0.5338(7) 0.3043(5) 0.2952(4) 0.045(2) 1.000 Uani d
C(13) 0.3298(7) 0.3403(5) 0.1850(4) 0.037(2) 1.000 Uani d
C(14) 0.2682(11) 0.2070(7) 0.0773(5) 0.089(3) 1.000 Uani d
C(15a) 0.194(5) 0.095(4) 0.093(3) 0.160(16) 0.400 Uiso d
C(15) 0.268(3) 0.093(2) 0.0647(13) 0.136(8) 0.600 Uiso d
C(16) 0.2125(19) 0.0356(13) 0.1211(9) 0.088(5) 0.600 Uiso d
C(16a) 0.131(3) 0.029(2) 0.0375(16) 0.124(9) 0.400 Uiso d
H(1) 0.3131 0.0737 0.7534 0.054 1.000 Uiso c
H(2) 0.4020 0.2699 0.6298 0.047 1.000 Uiso c
H(3) 0.4127 0.4433 0.2659 0.049 1.000 Uiso c
H(4) 0.4284 0.1990 0.1789 0.065 1.000 Uiso c
H(5) 0.4532 0.2832 0.9211 0.159 1.000 Uiso c
H(6) 0.3644 0.1858 0.8818 0.159 1.000 Uiso c
H(7) 0.5373 0.1757 0.9095 0.159 1.000 Uiso c
H(8) 0.4180 0.3097 0.7881 0.136 1.000 Uiso c
H(9) 0.5906 0.2952 0.8147 0.136 1.000 Uiso c
H(10) 0.5632 0.1163 0.7737 0.073 1.000 Uiso c
H(11) 0.5454 0.2001 0.7056 0.073 1.000 Uiso c
H(12) 0.1426 0.2365 0.5238 0.051 1.000 Uiso c
H(13) 0.2498 0.3355 0.5246 0.051 1.000 Uiso c
H(14) 0.2931 0.0537 0.4947 0.058 1.000 Uiso c
H(15) 0.4227 -0.0213 0.3964 0.074 1.000 Uiso c
H(16) 0.5293 0.0905 0.3067 0.065 1.000 Uiso c
H(17) 0.3787 0.3491 0.4163 0.042 1.000 Uiso c
H(18) 0.5839 0.2612 0.2600 0.054 1.000 Uiso c
H(19) 0.6059 0.3501 0.3244 0.054 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 64 0.002 0.002
;International Tables for Crystallography
(1992, Vol. C, Tables 4.2.6.8 and 6.1.1.1)
;
H 0 104 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
4 3 -1
3 1 -7
-3 1 7
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(3) N(1) C(4) 126.2(6) yes
C(3) N(1) H(1) 116.9 no
C(4) N(1) H(1) 116.9 no
C(4) N(2) C(5) 126.2(5) yes
C(4) N(2) H(2) 116.9 no
C(5) N(2) H(2) 116.9 no
C(12) N(3) C(13) 126.3(5) yes
C(12) N(3) H(3) 116.8 no
C(13) N(3) H(3) 116.8 no
C(13) N(4) C(14) 123.6(6) yes
C(13) N(4) H(4) 118.2 no
C(14) N(4) H(4) 118.2 no
C(2) C(1) H(5) 109.5 no
C(2) C(1) H(6) 109.5 no
C(2) C(1) H(7) 109.5 no
H(5) C(1) H(6) 109.5 no
H(5) C(1) H(7) 109.5 no
H(6) C(1) H(7) 109.5 no
C(1) C(2) C(3) 114.0(9) yes
C(1) C(2) H(8) 108.3 no
C(1) C(2) H(9) 108.3 no
C(3) C(2) H(8) 108.3 no
C(3) C(2) H(9) 108.3 no
H(8) C(2) H(9) 109.5 no
N(1) C(3) C(2) 114.2(7) yes
N(1) C(3) H(10) 108.3 no
N(1) C(3) H(11) 108.3 no
C(2) C(3) H(10) 108.3 no
C(2) C(3) H(11) 108.3 no
H(10) C(3) H(11) 109.5 no
S(1) C(4) N(1) 118.7(5) yes
S(1) C(4) N(2) 122.1(5) yes
N(1) C(4) N(2) 119.2(6) yes
N(2) C(5) C(6) 112.6(5) yes
N(2) C(5) H(12) 108.7 no
N(2) C(5) H(13) 108.7 no
C(6) C(5) H(12) 108.7 no
C(6) C(5) H(13) 108.7 no
H(12) C(5) H(13) 109.5 no
C(5) C(6) C(7) 121.5(6) yes
C(5) C(6) C(11) 120.1(6) yes
C(7) C(6) C(11) 118.4(6) yes
C(6) C(7) C(8) 120.7(6) yes
C(6) C(7) H(14) 119.7 no
C(8) C(7) H(14) 119.7 no
C(7) C(8) C(9) 119.7(6) yes
C(7) C(8) H(15) 120.1 no
C(9) C(8) H(15) 120.1 no
C(8) C(9) C(10) 120.8(6) yes
C(8) C(9) H(16) 119.6 no
C(10) C(9) H(16) 119.6 no
C(9) C(10) C(11) 117.7(6) yes
C(9) C(10) C(12) 121.3(6) yes
C(11) C(10) C(12) 121.0(5) yes
C(6) C(11) C(10) 122.7(6) yes
C(6) C(11) H(17) 118.6 no
C(10) C(11) H(17) 118.6 no
N(3) C(12) C(10) 113.2(5) yes
N(3) C(12) H(18) 108.5 no
N(3) C(12) H(19) 108.5 no
C(10) C(12) H(18) 108.5 no
C(10) C(12) H(19) 108.5 no
H(18) C(12) H(19) 109.5 no
S(2) C(13) N(3) 119.1(5) yes
S(2) C(13) N(4) 122.1(5) yes
N(3) C(13) N(4) 118.8(6) yes
N(4) C(14) C(15a) 108.5(17) yes
N(4) C(14) C(15) 115.9(11) yes
C(14) C(15a) C(16a) 125.7(35) yes
C(14) C(15) C(16) 114.7(18) yes
C(14) C(15) C(16a) 124.8(19) yes
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_publ_flag
S(1) C(4) 1.722(6) yes
S(2) C(13) 1.697(6) yes
N(1) C(3) 1.457(8) yes
N(1) C(4) 1.331(7) yes
N(1) H(1) 0.95 no
N(2) C(4) 1.329(7) yes
N(2) C(5) 1.458(7) yes
N(2) H(2) 0.95 no
N(3) C(12) 1.450(7) yes
N(3) C(13) 1.338(7) yes
N(3) H(3) 0.95 no
N(4) C(13) 1.330(7) yes
N(4) C(14) 1.486(8) yes
N(4) H(4) 0.95 no
C(1) C(2) 1.488(12) yes
C(1) H(5) 0.95 no
C(1) H(6) 0.95 no
C(1) H(7) 0.95 no
C(2) C(3) 1.482(11) yes
C(2) H(8) 0.95 no
C(2) H(9) 0.95 no
C(3) H(10) 0.95 no
C(3) H(11) 0.95 no
C(5) C(6) 1.498(8) yes
C(5) H(12) 0.95 no
C(5) H(13) 0.95 no
C(6) C(7) 1.375(8) yes
C(6) C(11) 1.372(8) yes
C(7) C(8) 1.379(9) yes
C(7) H(14) 0.95 no
C(8) C(9) 1.393(9) yes
C(8) H(15) 0.95 no
C(9) C(10) 1.375(8) yes
C(9) H(16) 0.95 no
C(10) C(11) 1.390(7) yes
C(10) C(12) 1.502(8) yes
C(11) H(17) 0.95 no
C(12) H(18) 0.95 no
C(12) H(19) 0.95 no
C(14) C(15a) 1.57(5) yes
C(14) C(15) 1.43(3) yes
C(15a) C(16a) 1.33(4) yes
C(15) C(16) 1.33(3) yes
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(3) 3.382(5) 2_546 no
S(1) N(2) 3.405(5) 4_455 no
S(2) N(1) 3.409(5) 2_556 no
C(5) C(11) 3.565(8) 4_455 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(4) N(1) C(3) 177.1(5) no
S(1) C(4) N(2) C(5) -7.9(9) no
S(2) C(13) N(3) C(12) 170.0(5) no
S(2) C(13) N(4) C(14) 6.4(9) no
N(1) C(3) C(2) C(1) 72.0(10) no
N(1) C(4) N(2) C(5) 172.6(5) no
N(2) C(4) N(1) C(3) -3.4(10) no
N(2) C(5) C(6) C(7) 59.4(8) no
N(2) C(5) C(6) C(11) -120.4(6) no
N(3) C(12) C(10) C(9) 118.8(7) no
N(3) C(12) C(10) C(11) -61.1(8) no
N(3) C(13) N(4) C(14) -174.1(7) no
N(4) C(13) N(3) C(12) -9.6(9) no
N(4) C(14) C(15a) C(16a) -168.1(34) no
N(4) C(14) C(15) C(16) 57.3(22) no
C(2) C(3) N(1) C(4) 97.7(8) no
C(4) N(2) C(5) C(6) -97.4(7) no
C(5) C(6) C(7) C(8) -178.7(6) no
C(5) C(6) C(11) C(10) 178.9(5) no
C(6) C(7) C(8) C(9) -0.8(11) no
C(6) C(11) C(10) C(9) 0.5(9) no
C(6) C(11) C(10) C(12) -179.6(6) no
C(7) C(6) C(11) C(10) -0.9(9) no
C(7) C(8) C(9) C(10) 0.3(11) no
C(8) C(7) C(6) C(11) 1.1(10) no
C(8) C(9) C(10) C(11) -0.1(10) no
C(8) C(9) C(10) C(12) 180.0(6) no
C(10) C(12) N(3) C(13) -79.9(7) no
C(13) N(4) C(14) C(15a) -124.9(18) no
C(13) N(4) C(14) C(15) -159.3(12) no
