#------------------------------------------------------------------------------
#$Date: 2017-10-14 22:27:35 +0300 (Sat, 14 Oct 2017) $
#$Revision: 202017 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/20/56/7205695.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_7205695
loop_
_publ_author_name
'Lenthall, Joseph T.'
'Foster, Jonathan A.'
'Anderson, Kirsty M.'
'Probert, Michael R.'
'Howard, Judith A. K.'
'Steed, Jonathan W.'
_publ_section_title
;
 Hydrogen bonding interactions with the thiocarbonyl π-system
;
_journal_issue                   9
_journal_name_full               CrystEngComm
_journal_page_first              3202
_journal_paper_doi               10.1039/c0ce00680g
_journal_volume                  13
_journal_year                    2011
_chemical_formula_moiety         'C14 H22 N4 S2'
_chemical_formula_sum            'C14 H22 N4 S2'
_chemical_formula_weight         310.48
_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                78.9840(10)
_cell_angle_beta                 66.4850(10)
_cell_angle_gamma                65.0450(10)
_cell_formula_units_Z            2
_cell_length_a                   9.4599(6)
_cell_length_b                   9.5946(6)
_cell_length_c                   11.0971(7)
_cell_measurement_temperature    120(2)
_cell_volume                     837.03(9)
_computing_cell_refinement       SMART
_computing_data_collection       SMART
_computing_data_reduction        SAINT
_computing_molecular_graphics    XP
_computing_publication_material  XP
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      120(2)
_diffrn_measured_fraction_theta_full 0.919
_diffrn_measured_fraction_theta_max 0.919
_diffrn_measurement_device_type  'SMART 1k'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0439
_diffrn_reflns_av_sigmaI/netI    0.0479
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            8785
_diffrn_reflns_theta_full        30.04
_diffrn_reflns_theta_max         30.04
_diffrn_reflns_theta_min         2.00
_exptl_absorpt_coefficient_mu    0.315
_exptl_absorpt_correction_T_max  0.963
_exptl_absorpt_correction_T_min  0.924
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   SADABS
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.232
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             332
_exptl_crystal_size_max          0.28
_exptl_crystal_size_mid          0.21
_exptl_crystal_size_min          0.12
_refine_diff_density_max         0.358
_refine_diff_density_min         -0.349
_refine_diff_density_rms         0.055
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.018
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     181
_refine_ls_number_reflns         4507
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.018
_refine_ls_R_factor_all          0.0531
_refine_ls_R_factor_gt           0.0392
_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)+(0.0342P)²+0.4676P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0918
_refine_ls_wR_factor_ref         0.0986
_reflns_number_gt                3673
_reflns_number_total             4507
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            c0ce00680g.txt
_cod_data_source_block           x:\groupc~1\joelen~1\06srv2~1\frm_m
_cod_depositor_comments
;
The following automatic conversions were performed:
'_symmetry_cell_setting' value 'Triclinic' changed to 'triclinic'
according to '/home/saulius/struct/CIF-dictionaries/cif_core.dic'
dictionary named 'cif_core.dic' version 2.4.1 from 2010-06-29.

Automatic conversion script
Id: cif_fix_enum 1555 2011-01-17 13:19:09Z saulius 
;
_cod_original_sg_symbol_H-M      P-1
_cod_database_code               7205695
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 0.39540(5) 0.54798(4) 0.34386(4) 0.01968(10) Uani 1 1 d . . .
S2 S -0.26011(5) 0.94895(5) 0.65841(4) 0.02222(10) Uani 1 1 d . . .
N1 N 0.09372(16) 0.76393(15) 0.46540(12) 0.0183(3) Uani 1 1 d . . .
H1N H 0.0277 0.8287 0.5299 0.022 Uiso 1 1 calc R . .
N2 N 0.29778(17) 0.70957(15) 0.54894(13) 0.0205(3) Uani 1 1 d . . .
H2N H 0.4023 0.6563 0.5425 0.025 Uiso 1 1 calc R . .
N3 N -0.19003(17) 0.68085(16) 0.56058(13) 0.0217(3) Uani 1 1 d . . .
H3N H -0.1979 0.5904 0.5774 0.026 Uiso 1 1 calc R . .
N4 N -0.29609(18) 0.69146(17) 0.78216(13) 0.0246(3) Uani 1 1 d . . .
H4N H -0.2865 0.5971 0.7780 0.029 Uiso 1 1 calc R . .
C1 C 0.02309(19) 0.75434(17) 0.37740(15) 0.0180(3) Uani 1 1 d . . .
C2 C 0.0934(2) 0.78229(19) 0.24272(16) 0.0220(3) Uani 1 1 d . . .
H2 H 0.1860 0.8123 0.2102 0.026 Uiso 1 1 calc R . .
C3 C 0.0285(2) 0.7664(2) 0.15652(16) 0.0267(4) Uani 1 1 d . . .
H3 H 0.0778 0.7839 0.0649 0.032 Uiso 1 1 calc R . .
C4 C -0.1088(2) 0.7248(2) 0.20420(18) 0.0295(4) Uani 1 1 d . . .
H4 H -0.1515 0.7112 0.1448 0.035 Uiso 1 1 calc R . .
C5 C -0.1835(2) 0.7032(2) 0.33806(17) 0.0265(4) Uani 1 1 d . . .
H5 H -0.2794 0.6780 0.3703 0.032 Uiso 1 1 calc R . .
C6 C -0.11890(19) 0.71808(18) 0.42615(15) 0.0198(3) Uani 1 1 d . . .
C7 C 0.25212(19) 0.68330(16) 0.45940(14) 0.0168(3) Uani 1 1 d . . .
C8 C -0.24803(19) 0.76678(18) 0.66759(15) 0.0198(3) Uani 1 1 d . . .
C9 C 0.1938(2) 0.81731(19) 0.65737(17) 0.0264(4) Uani 1 1 d . . .
H9 H 0.1101 0.9081 0.6287 0.032 Uiso 1 1 calc R . .
C10 C 0.3082(3) 0.8715(2) 0.6843(2) 0.0420(5) Uani 1 1 d . . .
H10A H 0.3648 0.9193 0.6041 0.063 Uiso 1 1 calc R . .
H10B H 0.3914 0.7833 0.7118 0.063 Uiso 1 1 calc R . .
H10C H 0.2418 0.9467 0.7542 0.063 Uiso 1 1 calc R . .
C11 C 0.1010(3) 0.7410(3) 0.77769(19) 0.0419(5) Uani 1 1 d . . .
H11A H 0.0303 0.7075 0.7550 0.063 Uiso 1 1 calc R . .
H11B H 0.0311 0.8148 0.8486 0.063 Uiso 1 1 calc R . .
H11C H 0.1818 0.6518 0.8067 0.063 Uiso 1 1 calc R . .
C12 C -0.3630(2) 0.7532(2) 0.91327(16) 0.0254(3) Uani 1 1 d . . .
H12 H -0.3047 0.8204 0.9107 0.030 Uiso 1 1 calc R . .
C13 C -0.3214(3) 0.6183(2) 1.00801(18) 0.0373(4) Uani 1 1 d . . .
H13A H -0.2003 0.5605 0.9778 0.056 Uiso 1 1 calc R . .
H13B H -0.3769 0.5507 1.0114 0.056 Uiso 1 1 calc R . .
H13C H -0.3601 0.6568 1.0959 0.056 Uiso 1 1 calc R . .
C14 C -0.5493(2) 0.8494(2) 0.95571(18) 0.0347(4) Uani 1 1 d . . .
H14A H -0.5704 0.9348 0.8923 0.052 Uiso 1 1 calc R . .
H14B H -0.5890 0.8902 1.0428 0.052 Uiso 1 1 calc R . .
H14C H -0.6086 0.7851 0.9594 0.052 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'
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
C7 N1 C1 126.11(13) . . ?
C7 N1 H1N 116.9 . . ?
C1 N1 H1N 116.9 . . ?
C7 N2 C9 127.43(13) . . ?
C7 N2 H2N 116.3 . . ?
C9 N2 H2N 116.3 . . ?
C8 N3 C6 128.52(13) . . ?
C8 N3 H3N 115.7 . . ?
C6 N3 H3N 115.7 . . ?
C8 N4 C12 125.58(14) . . ?
C8 N4 H4N 117.2 . . ?
C12 N4 H4N 117.2 . . ?
C2 C1 C6 119.83(14) . . ?
C2 C1 N1 120.43(14) . . ?
C6 C1 N1 119.74(14) . . ?
C3 C2 C1 120.26(15) . . ?
C3 C2 H2 119.9 . . ?
C1 C2 H2 119.9 . . ?
C2 C3 C4 119.98(15) . . ?
C2 C3 H3 120.0 . . ?
C4 C3 H3 120.0 . . ?
C5 C4 C3 120.08(16) . . ?
C5 C4 H4 120.0 . . ?
C3 C4 H4 120.0 . . ?
C4 C5 C6 120.55(16) . . ?
C4 C5 H5 119.7 . . ?
C6 C5 H5 119.7 . . ?
C5 C6 C1 119.20(14) . . ?
C5 C6 N3 118.32(14) . . ?
C1 C6 N3 122.18(14) . . ?
N2 C7 N1 117.90(13) . . ?
N2 C7 S1 118.90(12) . . ?
N1 C7 S1 123.19(11) . . ?
N4 C8 N3 112.92(14) . . ?
N4 C8 S2 123.14(12) . . ?
N3 C8 S2 123.94(12) . . ?
N2 C9 C10 107.41(15) . . ?
N2 C9 C11 110.51(15) . . ?
C10 C9 C11 112.70(17) . . ?
N2 C9 H9 108.7 . . ?
C10 C9 H9 108.7 . . ?
C11 C9 H9 108.7 . . ?
C9 C10 H10A 109.5 . . ?
C9 C10 H10B 109.5 . . ?
H10A C10 H10B 109.5 . . ?
C9 C10 H10C 109.5 . . ?
H10A C10 H10C 109.5 . . ?
H10B C10 H10C 109.5 . . ?
C9 C11 H11A 109.5 . . ?
C9 C11 H11B 109.5 . . ?
H11A C11 H11B 109.5 . . ?
C9 C11 H11C 109.5 . . ?
H11A C11 H11C 109.5 . . ?
H11B C11 H11C 109.5 . . ?
N4 C12 C14 111.82(15) . . ?
N4 C12 C13 107.77(15) . . ?
C14 C12 C13 112.19(15) . . ?
N4 C12 H12 108.3 . . ?
C14 C12 H12 108.3 . . ?
C13 C12 H12 108.3 . . ?
C12 C13 H13A 109.5 . . ?
C12 C13 H13B 109.5 . . ?
H13A C13 H13B 109.5 . . ?
C12 C13 H13C 109.5 . . ?
H13A C13 H13C 109.5 . . ?
H13B C13 H13C 109.5 . . ?
C12 C14 H14A 109.5 . . ?
C12 C14 H14B 109.5 . . ?
H14A C14 H14B 109.5 . . ?
C12 C14 H14C 109.5 . . ?
H14A C14 H14C 109.5 . . ?
H14B C14 H14C 109.5 . . ?
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 C7 1.7121(15) . ?
S2 C8 1.6885(16) . ?
N1 C7 1.3455(19) . ?
N1 C1 1.4196(19) . ?
N1 H1N 0.8800 . ?
N2 C7 1.3296(19) . ?
N2 C9 1.469(2) . ?
N2 H2N 0.8800 . ?
N3 C8 1.3651(19) . ?
N3 C6 1.416(2) . ?
N3 H3N 0.8800 . ?
N4 C8 1.345(2) . ?
N4 C12 1.465(2) . ?
N4 H4N 0.8800 . ?
C1 C2 1.397(2) . ?
C1 C6 1.400(2) . ?
C2 C3 1.385(2) . ?
C2 H2 0.9500 . ?
C3 C4 1.391(3) . ?
C3 H3 0.9500 . ?
C4 C5 1.385(2) . ?
C4 H4 0.9500 . ?
C5 C6 1.398(2) . ?
C5 H5 0.9500 . ?
C9 C10 1.523(3) . ?
C9 C11 1.524(3) . ?
C9 H9 1.0000 . ?
C10 H10A 0.9800 . ?
C10 H10B 0.9800 . ?
C10 H10C 0.9800 . ?
C11 H11A 0.9800 . ?
C11 H11B 0.9800 . ?
C11 H11C 0.9800 . ?
C12 C14 1.520(3) . ?
C12 C13 1.522(3) . ?
C12 H12 1.0000 . ?
C13 H13A 0.9800 . ?
C13 H13B 0.9800 . ?
C13 H13C 0.9800 . ?
C14 H14A 0.9800 . ?
C14 H14B 0.9800 . ?
C14 H14C 0.9800 . ?
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 26667019
