#------------------------------------------------------------------------------
#$Date: 2017-10-13 14:42:48 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201982 $
#$URL: file:///home/coder/svn-repositories/cod/cif/4/02/37/4023765.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_4023765
loop_
_publ_author_name
'Lidaris San Miguel'
'Adam J. Matzger'
_publ_section_title
;
 Regiochemical Effects of Sulfur Oxidation on the Electronic
 and Solid-State Properties of Planarized Oligothiophenes
 Containing Thieno[3,2-b]thiophene Units
;
_journal_name_full               'Journal of Organic Chemistry'
_journal_page_first              7882
_journal_page_last               7888
_journal_paper_doi               10.1021/jo801619q
_journal_volume                  73
_journal_year                    2008
_chemical_formula_moiety         'C12 H6 O2 S4'
_chemical_formula_sum            'C12 H6 O2 S4'
_chemical_formula_weight         310.41
_chemical_name_systematic
; 
[2,2']Bi[thieno[3,2-b]thiophenyl] 4,4-dioxide
;
_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'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 93.253(5)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   8.4033(6)
_cell_length_b                   10.5626(8)
_cell_length_c                   13.6778(12)
_cell_measurement_reflns_used    3903
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      66.6
_cell_measurement_theta_min      6.7
_cell_volume                     1212.10(17)
_computing_cell_refinement       PROCESS-AUTO
_computing_data_collection       PROCESS-AUTO
_computing_data_reduction        'CrystalStructure 3.8'
_computing_publication_material  'CrystalStructure 3.8'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    SIR2004
_diffrn_ambient_temperature      100(2)
_diffrn_detector_area_resol_mean 10.00
_diffrn_measured_fraction_theta_full 0.995
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measurement_device_type  'Rigaku RAXIS-Spider'
_diffrn_measurement_method       ω
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54187
_diffrn_reflns_av_R_equivalents  0.0278
_diffrn_reflns_av_sigmaI/netI    0.0157
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            20908
_diffrn_reflns_theta_full        66.62
_diffrn_reflns_theta_max         66.62
_diffrn_reflns_theta_min         6.74
_exptl_absorpt_coefficient_mu    7.118
_exptl_absorpt_correction_T_max  0.8707
_exptl_absorpt_correction_T_min  0.5997
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
    Higashi, T. (1995). Program for Absorption Correction.
    Rigaku Corporation, Tokyo, Japan.
;
_exptl_crystal_colour            Yellow
_exptl_crystal_density_diffrn    1.701
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             632
_exptl_crystal_size_max          0.08
_exptl_crystal_size_mid          0.08
_exptl_crystal_size_min          0.02
_refine_diff_density_max         0.469
_refine_diff_density_min         -0.277
_refine_diff_density_rms         0.071
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.093
_refine_ls_hydrogen_treatment    riding
_refine_ls_matrix_type           full
_refine_ls_number_parameters     164
_refine_ls_number_reflns         2125
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.093
_refine_ls_R_factor_all          0.0327
_refine_ls_R_factor_gt           0.0310
_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)+(0.0430P)²+1.3648P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0833
_refine_ls_wR_factor_ref         0.0844
_reflns_number_gt                1989
_reflns_number_total             2125
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jo801619q_si_002.cif
_cod_data_source_block           O2T2-T2_compound_2
_cod_original_sg_symbol_H-M      'P 21/a'
_cod_database_code               4023765
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_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 0.14084(6) 0.49301(5) 0.38453(4) 0.01472(16) Uani 1 1 d . . .
S2 S 0.38311(7) 0.25610(5) 0.20361(4) 0.01793(16) Uani 1 1 d . . .
S3 S 0.25096(6) 0.48716(5) -0.05599(4) 0.01725(16) Uani 1 1 d . . .
S4 S 0.54455(6) 0.26346(5) -0.21920(4) 0.01906(16) Uani 1 1 d . . .
O1 O -0.03037(18) 0.48521(15) 0.37766(12) 0.0216(4) Uani 1 1 d . . .
O2 O 0.21086(19) 0.61232(14) 0.41239(11) 0.0220(4) Uani 1 1 d . . .
C1 C 0.2209(3) 0.3684(2) 0.45912(16) 0.0186(5) Uani 1 1 d . . .
H1 H 0.2081 0.3609 0.5274 0.022 Uiso 1 1 calc R . .
C2 C 0.3017(3) 0.2868(2) 0.40641(16) 0.0203(5) Uani 1 1 d . . .
H2 H 0.3532 0.2134 0.4329 0.024 Uiso 1 1 calc R . .
C3 C 0.3017(3) 0.3232(2) 0.30312(16) 0.0166(4) Uani 1 1 d . . .
C4 C 0.2205(2) 0.43097(19) 0.27785(15) 0.0141(4) Uani 1 1 d . . .
C5 C 0.2210(2) 0.4636(2) 0.17769(16) 0.0144(4) Uani 1 1 d . . .
H3 H 0.1696 0.5358 0.1491 0.017 Uiso 1 1 calc R . .
C6 C 0.3061(2) 0.37623(19) 0.12719(15) 0.0144(4) Uani 1 1 d . . .
C7 C 0.3397(2) 0.37483(19) 0.02469(15) 0.0145(4) Uani 1 1 d . . .
C8 C 0.4407(3) 0.2935(2) -0.02141(15) 0.0165(4) Uani 1 1 d . . .
H4 H 0.4980 0.2260 0.0100 0.020 Uiso 1 1 calc R . .
C9 C 0.4471(2) 0.3252(2) -0.12269(15) 0.0153(4) Uani 1 1 d . . .
C10 C 0.3528(2) 0.4275(2) -0.15197(16) 0.0150(4) Uani 1 1 d . . .
C11 C 0.3588(2) 0.4581(2) -0.25422(15) 0.0151(4) Uani 1 1 d . . .
H5 H 0.3030 0.5257 -0.2866 0.018 Uiso 1 1 calc R . .
C12 C 0.4573(2) 0.3744(2) -0.29764(16) 0.0181(5) Uani 1 1 d . . .
H6 H 0.4761 0.3773 -0.3654 0.022 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 0.0181 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'
S S 0.3331 0.5567 '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'
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
O2 S1 O1 117.49(9) . . ?
O2 S1 C4 112.14(9) . . ?
O1 S1 C4 110.45(10) . . ?
O2 S1 C1 111.26(10) . . ?
O1 S1 C1 109.91(10) . . ?
C4 S1 C1 92.90(10) . . ?
C3 S2 C6 91.38(10) . . ?
C10 S3 C7 91.15(10) . . ?
C9 S4 C12 90.91(11) . . ?
C2 C1 S1 110.89(17) . . ?
C2 C1 H1 124.6 . . ?
S1 C1 H1 124.6 . . ?
C1 C2 C3 112.3(2) . . ?
C1 C2 H2 123.8 . . ?
C3 C2 H2 123.8 . . ?
C4 C3 C2 115.89(19) . . ?
C4 C3 S2 111.19(16) . . ?
C2 C3 S2 132.92(17) . . ?
C3 C4 C5 114.90(19) . . ?
C3 C4 S1 107.97(16) . . ?
C5 C4 S1 137.13(17) . . ?
C6 C5 C4 110.68(19) . . ?
C6 C5 H3 124.7 . . ?
C4 C5 H3 124.7 . . ?
C5 C6 C7 128.9(2) . . ?
C5 C6 S2 111.86(16) . . ?
C7 C6 S2 119.18(16) . . ?
C8 C7 C6 127.3(2) . . ?
C8 C7 S3 112.46(16) . . ?
C6 C7 S3 120.21(16) . . ?
C7 C8 C9 110.7(2) . . ?
C7 C8 H4 124.6 . . ?
C9 C8 H4 124.6 . . ?
C10 C9 C8 114.23(19) . . ?
C10 C9 S4 111.29(16) . . ?
C8 C9 S4 134.48(17) . . ?
C9 C10 C11 113.89(19) . . ?
C9 C10 S3 111.40(16) . . ?
C11 C10 S3 134.69(17) . . ?
C12 C11 C10 109.39(19) . . ?
C12 C11 H5 125.3 . . ?
C10 C11 H5 125.3 . . ?
C11 C12 S4 114.51(17) . . ?
C11 C12 H6 122.7 . . ?
S4 C12 H6 122.7 . . ?
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 O2 1.4332(16) . ?
S1 O1 1.4388(16) . ?
S1 C4 1.766(2) . ?
S1 C1 1.774(2) . ?
S2 C3 1.711(2) . ?
S2 C6 1.745(2) . ?
S3 C10 1.727(2) . ?
S3 C7 1.757(2) . ?
S4 C9 1.721(2) . ?
S4 C12 1.724(2) . ?
C1 C2 1.334(3) . ?
C1 H1 0.9500 . ?
C2 C3 1.464(3) . ?
C2 H2 0.9500 . ?
C3 C4 1.362(3) . ?
C4 C5 1.413(3) . ?
C5 C6 1.377(3) . ?
C5 H3 0.9500 . ?
C6 C7 1.446(3) . ?
C7 C8 1.385(3) . ?
C8 C9 1.429(3) . ?
C8 H4 0.9500 . ?
C9 C10 1.386(3) . ?
C10 C11 1.439(3) . ?
C11 C12 1.369(3) . ?
C11 H5 0.9500 . ?
C12 H6 0.9500 . ?
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_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
O2 S1 C1 C2 -115.09(18) . . . . ?
O1 S1 C1 C2 113.02(18) . . . . ?
C4 S1 C1 C2 0.04(18) . . . . ?
S1 C1 C2 C3 0.2(3) . . . . ?
C1 C2 C3 C4 -0.5(3) . . . . ?
C1 C2 C3 S2 -179.71(19) . . . . ?
C6 S2 C3 C4 0.14(17) . . . . ?
C6 S2 C3 C2 179.4(2) . . . . ?
C2 C3 C4 C5 -179.45(19) . . . . ?
S2 C3 C4 C5 -0.1(2) . . . . ?
C2 C3 C4 S1 0.5(2) . . . . ?
S2 C3 C4 S1 179.88(11) . . . . ?
O2 S1 C4 C3 114.06(16) . . . . ?
O1 S1 C4 C3 -112.82(16) . . . . ?
C1 S1 C4 C3 -0.31(17) . . . . ?
O2 S1 C4 C5 -66.0(2) . . . . ?
O1 S1 C4 C5 67.1(2) . . . . ?
C1 S1 C4 C5 179.6(2) . . . . ?
C3 C4 C5 C6 0.0(3) . . . . ?
S1 C4 C5 C6 -179.99(18) . . . . ?
C4 C5 C6 C7 -178.4(2) . . . . ?
C4 C5 C6 S2 0.1(2) . . . . ?
C3 S2 C6 C5 -0.16(16) . . . . ?
C3 S2 C6 C7 178.52(17) . . . . ?
C5 C6 C7 C8 172.0(2) . . . . ?
S2 C6 C7 C8 -6.5(3) . . . . ?
C5 C6 C7 S3 -6.6(3) . . . . ?
S2 C6 C7 S3 174.93(11) . . . . ?
C10 S3 C7 C8 -1.21(17) . . . . ?
C10 S3 C7 C6 177.59(17) . . . . ?
C6 C7 C8 C9 -177.7(2) . . . . ?
S3 C7 C8 C9 1.0(2) . . . . ?
C7 C8 C9 C10 -0.2(3) . . . . ?
C7 C8 C9 S4 -179.14(17) . . . . ?
C12 S4 C9 C10 -0.33(16) . . . . ?
C12 S4 C9 C8 178.7(2) . . . . ?
C8 C9 C10 C11 -179.46(18) . . . . ?
S4 C9 C10 C11 -0.2(2) . . . . ?
C8 C9 C10 S3 -0.8(2) . . . . ?
S4 C9 C10 S3 178.47(10) . . . . ?
C7 S3 C10 C9 1.09(16) . . . . ?
C7 S3 C10 C11 179.4(2) . . . . ?
C9 C10 C11 C12 0.9(3) . . . . ?
S3 C10 C11 C12 -177.44(18) . . . . ?
C10 C11 C12 S4 -1.1(2) . . . . ?
C9 S4 C12 C11 0.87(17) . . . . ?
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 30658771
