#------------------------------------------------------------------------------
#$Date: 2016-02-21 02:03:34 +0200 (Sun, 21 Feb 2016) $
#$Revision: 176798 $
#$URL: svn://www.crystallography.net/cod/cif/2/23/14/2231429.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/. The original data for this entry
# were provided by IUCr Journals, http://journals.iucr.org/.
#
# The file may be used within the scientific community so long as
# proper attribution is given to the journal article from which the
# data were obtained.
#
data_2231429
loop_
_publ_author_name
'Asiri, Abdullah M.'
'Faidallah, Hassan M.'
'Al-Youbi, Abdulrahman O.'
'Sobahi, Tarik R.'
'Ng, Seik Weng'
_publ_section_title
;
 (Z)-2-Sulfanylidene-5-(thiophen-2-ylmethylidene)imidazolidin-4-one
;
_journal_coeditor_code           BT5612
_journal_issue                   9
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o2429
_journal_paper_doi               10.1107/S1600536811033034
_journal_volume                  67
_journal_year                    2011
_chemical_formula_iupac          'C8 H6 N2 O S2'
_chemical_formula_moiety         'C8 H6 N2 O S2'
_chemical_formula_sum            'C8 H6 N2 O S2'
_chemical_formula_weight         210.27
_chemical_name_systematic
;
(Z)-2-Sulfanylidene-5-(thiophen-2-ylmethylidene)imidazolidin-4-one
;
_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                72.582(11)
_cell_angle_beta                 76.116(10)
_cell_angle_gamma                75.640(9)
_cell_formula_units_Z            2
_cell_length_a                   6.1022(6)
_cell_length_b                   7.0806(8)
_cell_length_c                   11.0425(13)
_cell_measurement_reflns_used    1386
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      73.92
_cell_measurement_theta_min      4.26
_cell_volume                     433.87(9)
_computing_cell_refinement       'CrysAlis PRO (Agilent, 2010)'
_computing_data_collection       'CrysAlis PRO (Agilent, 2010)'
_computing_data_reduction        'CrysAlis PRO (Agilent, 2010)'
_computing_molecular_graphics    'X-SEED (Barbour, 2001)'
_computing_publication_material  'publCIF (Westrip, 2010)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      100(2)
_diffrn_detector_area_resol_mean 10.4041
_diffrn_measured_fraction_theta_full 0.950
_diffrn_measured_fraction_theta_max 0.950
_diffrn_measurement_device_type
'Agilent SuperNova Dual diffractometer with an Atlas detector'
_diffrn_measurement_method       ω
_diffrn_radiation_monochromator  Mirror
_diffrn_radiation_source         'SuperNova (Cu) X-ray Source'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0273
_diffrn_reflns_av_sigmaI/netI    0.0376
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -4
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_number            2599
_diffrn_reflns_theta_full        74.09
_diffrn_reflns_theta_max         74.09
_diffrn_reflns_theta_min         4.27
_diffrn_standards_decay_%        0
_diffrn_standards_interval_count 0
_diffrn_standards_interval_time  0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    5.215
_exptl_absorpt_correction_T_max  0.9029
_exptl_absorpt_correction_T_min  0.3555
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(CrysAlis PRO; Agilent, 2010)'
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.610
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             216
_exptl_crystal_size_max          0.25
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.02
_refine_diff_density_max         0.329
_refine_diff_density_min         -0.443
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.039
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     134
_refine_ls_number_reflns         1677
_refine_ls_number_restraints     6
_refine_ls_restrained_S_all      1.038
_refine_ls_R_factor_all          0.0466
_refine_ls_R_factor_gt           0.0431
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.001
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0832P)²+0.1141P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1176
_refine_ls_wR_factor_ref         0.1224
_reflns_number_gt                1519
_reflns_number_total             1677
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            bt5612.cif
_cod_data_source_block           I
_cod_original_cell_volume        433.87(8)
_cod_database_code               2231429
_cod_database_fobs_code          2231429
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'
loop_
_atom_site_type_symbol
_atom_site_label
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_disorder_assembly
_atom_site_disorder_group
S S1 0.82425(8) 0.32671(8) 0.07136(5) 0.0212(2) Uani d . 1 1 . .
S S2 0.7731(2) 0.1352(3) 0.61560(16) 0.0177(3) Uani d PD 0.683(3) 1 A 1
O O1 0.0398(3) 0.3931(2) 0.34150(16) 0.0214(4) Uani d . 1 1 . .
N N1 0.3814(3) 0.3582(3) 0.19518(18) 0.0165(4) Uani d . 1 1 . .
H H1 0.3243 0.3831 0.1247 0.020 Uiso calc R 1 1 . .
N N2 0.6346(3) 0.2730(3) 0.32364(17) 0.0155(4) Uani d . 1 1 . .
H H2 0.7665 0.2340 0.3513 0.019 Uiso calc R 1 1 . .
C C1 0.6123(4) 0.3176(3) 0.1982(2) 0.0161(4) Uani d . 1 1 . .
C C2 0.2501(4) 0.3552(3) 0.3155(2) 0.0165(5) Uani d . 1 1 . .
C C3 0.4173(3) 0.2981(3) 0.4032(2) 0.0153(4) Uani d . 1 1 A .
C C4 0.3529(4) 0.2791(3) 0.5309(2) 0.0172(5) Uani d D 1 1 . .
H H4 0.1912 0.3066 0.5592 0.021 Uiso calc R 1 1 A 1
C C5 0.484(2) 0.225(8) 0.6318(12) 0.017(2) Uani d PD 0.683(3) 1 A 1
C C6 0.388(2) 0.234(2) 0.7571(9) 0.0201(7) Uani d PD 0.683(3) 1 A 1
H H6 0.2288 0.2766 0.7856 0.024 Uiso calc PR 0.683(3) 1 A 1
C C7 0.5563(7) 0.1717(7) 0.8394(5) 0.0218(9) Uani d PD 0.683(3) 1 A 1
H H7 0.5228 0.1714 0.9280 0.026 Uiso calc PR 0.683(3) 1 A 1
C C8 0.7709(9) 0.1127(9) 0.7737(4) 0.0227(12) Uani d PD 0.683(3) 1 A 1
H H8 0.9045 0.0645 0.8122 0.027 Uiso calc PR 0.683(3) 1 A 1
S S2' 0.3819(11) 0.2103(10) 0.7847(4) 0.0201(7) Uani d PD 0.317 1 A 2
C C5' 0.494(4) 0.210(17) 0.628(2) 0.017(2) Uani d PD 0.317 1 A 2
C C6' 0.731(3) 0.159(3) 0.6117(17) 0.0177(3) Uani d PD 0.317 1 A 2
H H6' 0.8277 0.1592 0.5304 0.021 Uiso calc PR 0.317(3) 1 A 2
C C7' 0.816(3) 0.106(2) 0.7307(10) 0.0227(12) Uani d PD 0.317 1 A 2
H H7' 0.9731 0.0609 0.7379 0.027 Uiso calc PR 0.317(3) 1 A 2
C C8' 0.6415(17) 0.1274(17) 0.8312(14) 0.0218(9) Uani d PD 0.317 1 A 2
H H8' 0.6628 0.0994 0.9177 0.026 Uiso calc PR 0.317(3) 1 A 2
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 '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 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.3331 0.5567 '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
C5 S2 C8 92.3(3)
C1 N1 C2 111.81(19)
C1 N1 H1 124.1
C2 N1 H1 124.1
C1 N2 C3 110.50(17)
C1 N2 H2 124.8
C3 N2 H2 124.8
N2 C1 N1 107.33(18)
N2 C1 S1 126.45(16)
N1 C1 S1 126.20(17)
O1 C2 N1 126.4(2)
O1 C2 C3 128.6(2)
N1 C2 C3 104.99(17)
C4 C3 N2 132.2(2)
C4 C3 C2 122.56(19)
N2 C3 C2 105.19(18)
C3 C4 C5' 128.4(9)
C3 C4 C5 131.6(5)
C3 C4 H4 114.2
C5' C4 H4 117.3
C5 C4 H4 114.2
C6 C5 C4 123.6(9)
C6 C5 S2 111.2(6)
C4 C5 S2 125.2(7)
C5 C6 C7 112.6(10)
C5 C6 H6 123.7
C7 C6 H6 123.7
C8 C7 C6 111.1(7)
C8 C7 H7 124.4
C6 C7 H7 124.4
C7 C8 S2 112.7(5)
C7 C8 H8 123.6
S2 C8 H8 123.6
C8' S2' C5' 93.5(8)
C6' C5' C4 128.4(16)
C6' C5' S2' 109.6(10)
C4 C5' S2' 121.5(14)
C5' C6' C7' 113.2(14)
C5' C6' H6' 123.4
C7' C6' H6' 123.4
C8' C7' C6' 111.3(16)
C8' C7' H7' 124.4
C6' C7' H7' 124.4
C7' C8' S2' 112.2(13)
C7' C8' H8' 123.9
S2' C8' H8' 123.9
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
S1 C1 1.660(2)
S2 C5 1.706(9)
S2 C8 1.702(5)
O1 C2 1.224(3)
N1 C1 1.373(3)
N1 C2 1.374(3)
N1 H1 0.8800
N2 C1 1.358(3)
N2 C3 1.407(3)
N2 H2 0.8800
C2 C3 1.476(3)
C3 C4 1.344(3)
C4 C5' 1.430(8)
C4 C5 1.431(5)
C4 H4 0.9500
C5 C6 1.380(13)
C6 C7 1.433(13)
C6 H6 0.9500
C7 C8 1.368(5)
C7 H7 0.9500
C8 H8 0.9500
S2' C8' 1.693(9)
S2' C5' 1.705(17)
C5' C6' 1.378(16)
C6' C7' 1.438(15)
C6' H6' 0.9500
C7' C8' 1.356(9)
C7' H7' 0.9500
C8' H8' 0.9500
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_site_symmetry_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_publ_flag
N2 H2 O1 1_655 0.88 2.20 2.873(2) 133 yes
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
C3 N2 C1 N1 -4.2(2)
C3 N2 C1 S1 174.52(16)
C2 N1 C1 N2 4.3(2)
C2 N1 C1 S1 -174.39(16)
C1 N1 C2 O1 177.1(2)
C1 N1 C2 C3 -2.7(2)
C1 N2 C3 C4 -177.4(2)
C1 N2 C3 C2 2.5(2)
O1 C2 C3 C4 0.3(3)
N1 C2 C3 C4 -179.96(19)
O1 C2 C3 N2 -179.7(2)
N1 C2 C3 N2 0.1(2)
C6 C7 C8 S2 1.0(8)
C5 S2 C8 C7 0.0(18)
C6' C7' C8' S2' -0.1(18)
