#------------------------------------------------------------------------------
#$Date: 2017-10-13 12:31:46 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201979 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/23/21/2232145.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_2232145
loop_
_publ_author_name
'Wen, Hua-wen'
'Fang, Qi'
_publ_section_title
;
 Thieno[3,4-d][1,3]dithiole-2-thione
;
_journal_coeditor_code           BG2422
_journal_issue                   11
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o3097
_journal_paper_doi               10.1107/S1600536811044084
_journal_volume                  67
_journal_year                    2011
_chemical_formula_iupac          'C5 H2 S4'
_chemical_formula_moiety         'C5 H2 S4'
_chemical_formula_sum            'C5 H2 S4'
_chemical_formula_weight         190.31
_chemical_name_systematic
;
Thieno[3,4-d][1,3]dithiole-2-thione
;
_space_group_IT_number           19
_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_Hall  'P 2ac 2ab'
_symmetry_space_group_name_H-M   'P 21 21 21'
_atom_sites_solution_hydrogens   difmap
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   3.94250(10)
_cell_length_b                   9.2588(2)
_cell_length_c                   19.2368(3)
_cell_measurement_reflns_used    6079
_cell_measurement_temperature    294(2)
_cell_measurement_theta_max      26.57
_cell_measurement_theta_min      2.44
_cell_volume                     702.20(3)
_computing_cell_refinement       'SAINT (Bruker, 2005)'
_computing_data_collection       'APEX2 (Bruker, 2005)'
_computing_data_reduction        'SAINT (Bruker, 2005)'
_computing_molecular_graphics    'SHELXTL (Sheldrick, 2008)'
_computing_publication_material  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      294(2)
_diffrn_detector_area_resol_mean 8.3
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_device_type  'Bruker APEX2 CCD area-detector'
_diffrn_measurement_method       'phi and omega scans'
_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  0.0298
_diffrn_reflns_av_sigmaI/netI    0.0148
_diffrn_reflns_limit_h_max       5
_diffrn_reflns_limit_h_min       -5
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       25
_diffrn_reflns_limit_l_min       -24
_diffrn_reflns_number            17824
_diffrn_reflns_theta_full        27.49
_diffrn_reflns_theta_max         27.49
_diffrn_reflns_theta_min         2.44
_exptl_absorpt_coefficient_mu    1.246
_exptl_absorpt_correction_T_max  0.9624
_exptl_absorpt_correction_T_min  0.7923
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SADABS; Bruker, 2005)'
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.800
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       bar
_exptl_crystal_F_000             384
_exptl_crystal_size_max          0.20
_exptl_crystal_size_mid          0.06
_exptl_crystal_size_min          0.03
_refine_diff_density_max         0.248
_refine_diff_density_min         -0.134
_refine_ls_abs_structure_details 'Flack (1983), 618 Friedel pairs'
_refine_ls_abs_structure_Flack   0.18(10)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.050
_refine_ls_hydrogen_treatment    refall
_refine_ls_matrix_type           full
_refine_ls_number_parameters     90
_refine_ls_number_reflns         1601
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.050
_refine_ls_R_factor_all          0.0248
_refine_ls_R_factor_gt           0.0213
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0337P)²+0.0176P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0512
_refine_ls_wR_factor_ref         0.0525
_reflns_number_gt                1486
_reflns_number_total             1601
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            bg2422.cif
_cod_data_source_block           I
_cod_database_code               2232145
_cod_database_fobs_code          2232145
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'-x, y+1/2, -z+1/2'
'x+1/2, -y+1/2, -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_occupancy
_atom_site_symmetry_multiplicity
S S1 0.00458(13) -0.19316(5) 0.07833(3) 0.04533(13) Uani d 1 1
S S2 -0.01295(11) 0.26695(5) 0.07145(2) 0.03376(11) Uani d 1 1
S S3 0.28209(12) 0.16829(5) 0.20312(2) 0.03822(12) Uani d 1 1
S S4 0.25260(16) 0.48015(5) 0.17223(3) 0.05033(14) Uani d 1 1
C C1 -0.0743(5) -0.0312(2) 0.03940(10) 0.0403(4) Uani d 1 1
C C2 0.0144(4) 0.08048(18) 0.08177(8) 0.0306(3) Uani d 1 1
C C3 0.1522(4) 0.03202(19) 0.14643(9) 0.0321(3) Uani d 1 1
C C4 0.1774(4) 0.31270(18) 0.15017(8) 0.0313(4) Uani d 1 1
C C5 0.1610(5) -0.1139(2) 0.15177(11) 0.0415(4) Uani d 1 1
H H1 -0.168(5) -0.030(2) -0.0057(13) 0.060(7) Uiso d 1 1
H H2 0.230(5) -0.162(2) 0.1886(10) 0.045(5) Uiso d 1 1
loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_12
_atom_site_aniso_U_13
_atom_site_aniso_U_23
S1 0.0560(3) 0.0293(2) 0.0507(3) 0.0022(2) -0.0044(3) -0.00404(19)
S2 0.0428(2) 0.0297(2) 0.0288(2) 0.0009(2) -0.00395(19) 0.00159(16)
S3 0.0476(2) 0.0372(2) 0.0299(2) 0.0011(2) -0.00840(19) 0.00048(17)
S4 0.0692(3) 0.0328(2) 0.0490(3) -0.0045(3) -0.0055(3) -0.0084(2)
C1 0.0485(11) 0.0348(9) 0.0377(10) 0.0017(9) -0.0078(8) -0.0023(8)
C2 0.0331(8) 0.0292(8) 0.0296(8) 0.0024(7) 0.0005(8) 0.0003(6)
C3 0.0336(8) 0.0323(9) 0.0303(8) 0.0014(7) 0.0015(6) 0.0023(7)
C4 0.0323(8) 0.0327(9) 0.0289(8) -0.0002(7) 0.0016(6) -0.0017(7)
C5 0.0527(11) 0.0326(10) 0.0391(10) 0.0054(8) -0.0018(8) 0.0027(8)
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'
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
C1 S1 C5 92.94(9)
C2 S2 C4 96.62(8)
C4 S3 C3 96.94(8)
C1 C2 C3 112.34(16)
C1 C2 S2 131.94(14)
C3 C2 S2 115.72(12)
C5 C3 C2 112.87(17)
C5 C3 S3 131.76(15)
C2 C3 S3 115.37(13)
C3 C5 S1 110.88(15)
C3 C5 H2 125.0(13)
S1 C5 H2 124.0(12)
C2 C1 S1 110.97(14)
C2 C1 H1 129.9(14)
S1 C1 H1 119.2(14)
S4 C4 S3 122.45(10)
S4 C4 S2 122.31(10)
S3 C4 S2 115.24(9)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
S1 C1 1.705(2)
S1 C5 1.707(2)
S2 C2 1.7412(17)
S2 C4 1.7422(17)
S3 C4 1.7308(17)
S3 C3 1.7445(18)
S4 C4 1.6345(17)
C2 C1 1.362(2)
C2 C3 1.429(2)
C3 C5 1.355(2)
C5 H2 0.879(19)
C1 H1 0.94(2)
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
C4 S2 C2 C1 -177.48(19)
C4 S2 C2 C3 3.09(15)
C1 C2 C3 C5 -0.7(2)
S2 C2 C3 C5 178.87(14)
C1 C2 C3 S3 178.54(13)
S2 C2 C3 S3 -1.92(18)
C4 S3 C3 C5 178.7(2)
C4 S3 C3 C2 -0.32(14)
C2 C3 C5 S1 0.3(2)
S3 C3 C5 S1 -178.73(11)
C1 S1 C5 C3 0.08(16)
C3 C2 C1 S1 0.7(2)
S2 C2 C1 S1 -178.73(12)
C5 S1 C1 C2 -0.46(16)
C3 S3 C4 S4 -177.35(11)
C3 S3 C4 S2 2.45(10)
C2 S2 C4 S4 176.50(11)
C2 S2 C4 S3 -3.29(11)
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 329771
