#------------------------------------------------------------------------------
#$Date: 2017-10-13 02:08:28 +0200 (vie 13 de oct de 2017) $
#$Revision: 201955 $
#$URL: svn://www.crystallography.net/cod/cif/2/00/55/2005514.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_2005514
loop_
_publ_author_name
'Ozturk, T.'
'Wallis, J. D.'
_publ_section_title
;
 6-(4-Methoxyphenyl)thieno[2,3-d][1,3]dithiole-2-thione at 150K
;
_journal_issue                   10
_journal_name_full               'Acta Crystallographica Section C'
_journal_page_first              2552
_journal_page_last               2554
_journal_paper_doi               10.1107/S0108270196005264
_journal_volume                  52
_journal_year                    1996
_chemical_formula_sum            'C12 H8 O S4'
_chemical_formula_weight         296.42
_chemical_name_systematic
;
6-(4-Methoxyphenyl)thieno[2,3-d]-1,3-dithiole-2-thione
;
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2yab'
_symmetry_space_group_name_H-M   'P 1 21/a 1'
_audit_creation_method           SHELXL
_cell_angle_alpha                90.00
_cell_angle_beta                 104.38(1)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   7.495(1)
_cell_length_b                   12.180(1)
_cell_length_c                   13.750(1)
_cell_measurement_reflns_used    250
_cell_measurement_temperature    150(2)
_cell_measurement_theta_max      25.0
_cell_measurement_theta_min      2.3
_cell_volume                     1215.9(2)
_computing_cell_refinement       SADONL
_computing_data_collection       'SADONL (Pflugrath & Messerschmidt, 1989)'
_computing_data_reduction        SADONL
_computing_molecular_graphics    'ZORTEP (Johnson, 1965)'
_computing_publication_material  SHELXL93
_computing_structure_refinement  'SHELXL93 (Sheldrick, 1993)'
_computing_structure_solution    'SHELXS86 (Sheldrick, 1985)'
_diffrn_measurement_device       'Enraf Nonius FAST system'
_diffrn_measurement_method
'Method: see Danopoulos, Wilkinson, Hussain-Bates & Hursthouse (1991)'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'rotating anode source'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71069
_diffrn_reflns_av_R_equivalents  0.0754
_diffrn_reflns_av_sigmaI/netI    0.0742
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            4990
_diffrn_reflns_theta_max         25.03
_diffrn_reflns_theta_min         2.27
_exptl_absorpt_coefficient_mu    0.758
_exptl_absorpt_correction_T_max  1.00
_exptl_absorpt_correction_T_min  0.80
_exptl_absorpt_correction_type   'refdelf (Walker & Stuart, 1983)'
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.619
_exptl_crystal_density_meas      ?
_exptl_crystal_description       plate
_exptl_crystal_F_000             608
_exptl_crystal_size_max          0.42
_exptl_crystal_size_mid          0.27
_exptl_crystal_size_min          0.10
_refine_diff_density_max         0.927
_refine_diff_density_min         -0.616
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_all   1.011
_refine_ls_goodness_of_fit_obs   1.098
_refine_ls_hydrogen_treatment    refall
_refine_ls_matrix_type           full
_refine_ls_number_parameters     186
_refine_ls_number_reflns         1826
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.011
_refine_ls_restrained_S_obs      1.098
_refine_ls_R_factor_all          0.0632
_refine_ls_R_factor_obs          0.0551
_refine_ls_shift/esd_max         0.054
_refine_ls_shift/esd_mean        0.009
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w = 1/[σ²(Fo²)+(0.0885P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_all         0.1312
_refine_ls_wR_factor_obs         0.1288
_reflns_number_observed          1522
_reflns_number_total             1826
_reflns_observed_criterion       >2sigma(I)
_cod_data_source_file            ha1162.cif
_cod_data_source_block           turan2
_cod_depositor_comments
;
The following automatic conversions were performed:

'_diffrn_ambient_temperature' value 'no' was changed to '?' - the
value is undefined or not given.

Automatic conversion script
Id: cif_fix_values 1715 2011-07-08 13:25:40Z adriana 

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 

The following automatic conversions were performed:

'_refine_ls_weighting_scheme' value 'calc w =
1/[\s^2^(Fo^2^)+(0.0885P)^2^] where P=(Fo^2^+2Fc^2^)/3' was changed
to 'calc'. New tag '_refine_ls_weighting_details' was created. The
value of the new tag was set to 'w = 1/[\s^2^(Fo^2^)+(0.0885P)^2^]
where P=(Fo^2^+2Fc^2^)/3'.

Automatic conversion script
Id: cif_fix_values 3143 2015-03-26 13:38:13Z robertas 
;
_cod_original_sg_symbol_H-M      'P 21/a'
_cod_database_code               2005514
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, y+1/2, -z'
'-x, -y, -z'
'x-1/2, -y-1/2, z'
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 0.0217(5) 0.0323(6) 0.0186(5) 0.0005(3) 0.0041(4) 0.0037(4)
S2 0.0330(6) 0.0534(7) 0.0279(6) 0.0097(4) 0.0051(4) 0.0144(5)
S3 0.0238(5) 0.0519(7) 0.0173(5) 0.0023(4) 0.0023(4) -0.0020(4)
S4 0.0299(6) 0.0365(6) 0.0257(6) -0.0051(4) 0.0035(4) -0.0087(4)
O1 0.0312(13) 0.0303(15) 0.0168(14) -0.0015(10) 0.0011(10) 0.0004(11)
C1 0.015(2) 0.051(3) 0.024(2) 0.001(2) 0.011(2) 0.000(2)
C2 0.020(2) 0.038(2) 0.023(2) -0.0009(15) 0.0047(15) -0.005(2)
C3 0.023(2) 0.030(2) 0.027(2) -0.002(2) 0.009(2) 0.000(2)
C4 0.014(2) 0.029(2) 0.025(2) 0.0012(13) 0.0076(14) -0.004(2)
C5 0.017(2) 0.033(2) 0.026(2) -0.0001(14) 0.0077(15) -0.002(2)
C6 0.015(2) 0.024(2) 0.023(2) 0.0047(13) 0.0065(14) 0.0008(15)
C7 0.023(2) 0.021(2) 0.022(2) 0.0010(14) 0.0028(14) 0.003(2)
C8 0.026(2) 0.022(2) 0.019(2) 0.0043(14) 0.0077(15) 0.010(2)
C9 0.014(2) 0.029(2) 0.020(2) 0.0061(13) 0.0012(13) -0.001(2)
C10 0.015(2) 0.025(2) 0.023(2) 0.0000(14) 0.0048(14) 0.0040(15)
C11 0.021(2) 0.025(2) 0.019(2) 0.0008(14) 0.0083(14) 0.004(2)
C12 0.036(2) 0.051(3) 0.018(2) -0.003(2) 0.000(2) 0.006(2)
loop_
_atom_site_label
_atom_site_occupancy
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_thermal_displace_type
_atom_site_calc_flag
_atom_site_type_symbol
S1 1 0.09374(12) 0.26719(8) 0.72981(7) 0.0244(3) Uani d S
S2 1 -0.10318(13) 0.38504(9) 0.54524(7) 0.0386(3) Uani d S
S3 1 -0.11270(11) 0.14127(9) 0.55835(7) 0.0315(3) Uani d S
S4 1 -0.02150(12) -0.06915(8) 0.68906(7) 0.0313(3) Uani d S
O1 1 0.5550(3) 0.2029(2) 1.2154(2) 0.0269(6) Uani d O
C1 1 -0.0464(5) 0.2706(3) 0.6073(3) 0.0289(9) Uani d C
C2 1 -0.0098(4) 0.0687(3) 0.6659(3) 0.0270(9) Uani d C
C3 1 0.1075(5) -0.0493(3) 0.8093(3) 0.0264(9) Uani d C
C4 1 0.1575(4) 0.0571(3) 0.8333(3) 0.0218(8) Uani d C
C5 1 0.0882(4) 0.1252(3) 0.7472(3) 0.0247(9) Uani d C
C6 1 0.2632(4) 0.0933(3) 0.9331(2) 0.0204(8) Uani d C
C7 1 0.2560(4) 0.0340(3) 1.0193(3) 0.0224(8) Uani d C
C8 1 0.3515(4) 0.0668(3) 1.1139(3) 0.0220(8) Uani d C
C9 1 0.4588(4) 0.1619(3) 1.1258(2) 0.0217(8) Uani d C
C10 1 0.4727(4) 0.2200(3) 1.0409(3) 0.0209(8) Uani d C
C11 1 0.3752(4) 0.1862(3) 0.9467(3) 0.0210(8) Uani d C
C12 1 0.5406(6) 0.1459(4) 1.3042(3) 0.0362(10) Uani d C
H3 1 0.1323(46) -0.1024(32) 0.8490(29) 0.027(11) Uiso d H
H7 1 0.1834(41) -0.0370(28) 1.0098(24) 0.016(8) Uiso d H
H8 1 0.3448(40) 0.0257(27) 1.1615(26) 0.011(9) Uiso d H
H10 1 0.5567(49) 0.2846(32) 1.0474(27) 0.031(10) Uiso d H
H11 1 0.3873(43) 0.2298(27) 0.8949(27) 0.013(9) Uiso d H
H121 1 0.6160(53) 0.1958(35) 1.3584(31) 0.041(11) Uiso d H
H122 1 0.5730(49) 0.0657(36) 1.3069(29) 0.035(11) Uiso d H
H123 1 0.4137(60) 0.1474(34) 1.3106(30) 0.050(13) Uiso d H
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 'Cromer and Mann (1968)'
H H 0.0000 0.0000 'Stewart, Davidson and Simpson (1965)'
O O 0.0106 0.0060 'Cromer and Mann (1968)'
S S 0.1246 0.1234 'Cromer and Mann (1968)'
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
C5 S1 C1 97.3(2)
C2 S3 C1 96.2(2)
C3 S4 C2 89.9(2)
C9 O1 C12 117.4(3)
S2 C1 S3 124.0(2)
S2 C1 S1 122.6(2)
S3 C1 S1 113.4(2)
C5 C2 S4 112.6(3)
C5 C2 S3 118.6(3)
S4 C2 S3 128.8(2)
C4 C3 S4 114.9(3)
C3 C4 C5 109.2(3)
C3 C4 C6 124.1(3)
C5 C4 C6 126.7(3)
C2 C5 C4 113.4(3)
C2 C5 S1 114.4(3)
C4 C5 S1 132.1(3)
C11 C6 C7 117.0(3)
C11 C6 C4 122.4(3)
C7 C6 C4 120.6(3)
C8 C7 C6 121.9(3)
C7 C8 C9 120.0(3)
O1 C9 C10 116.1(3)
O1 C9 C8 124.9(3)
C10 C9 C8 119.0(3)
C11 C10 C9 120.2(3)
C10 C11 C6 121.9(3)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
S1 C5 1.748(4)
S1 C1 1.751(4)
S2 C1 1.634(4)
S3 C2 1.730(4)
S3 C1 1.737(4)
S4 C3 1.713(4)
S4 C2 1.716(4)
O1 C9 1.359(4)
O1 C12 1.432(5)
C2 C5 1.362(5)
C3 C4 1.366(5)
C4 C5 1.433(5)
C4 C6 1.471(5)
C6 C11 1.394(5)
C6 C7 1.401(5)
C7 C8 1.379(5)
C8 C9 1.396(5)
C9 C10 1.391(5)
C10 C11 1.382(5)
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 9088746
