#Supplementary Material (ESI) for Journal of Materials Chemistry
#This journal is (c) The Royal Society of Chemistry 2010

data_global

_journal_coden_Cambridge         1145

loop_
_publ_author_name
'Wijsboom, Yair'
'Sheynin, Yana'
'Patra, Asit'
'Zamoshchik, Natalia'
'Vardimon, Ran'
'Leitusw, Gregory'
'Bendikov, Michael'

_publ_contact_author_name        'Bendikov, Michael'
_publ_contact_author_email       michael.bendikov@weizmann.ac.il

_publ_section_title              
;
Tuning of Electronic Properties and Rigidity in PEDOT Analogs
;

# Attachment '- bd69_1.cif'

data_bd69_1
_database_code_depnum_ccdc_archive 'CCDC 789741'
#TrackingRef '- bd69_1.cif'

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C12 H10 O2 S4'
_symmetry_space_group_name_Hall  -P2ybc
_chemical_formula_sum            'C12 H10 O2 S4'
_chemical_formula_weight         314.44

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'
O O 0.0106 0.0060 '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'

_symmetry_cell_setting           Monoclinic
_symmetry_space_group_name_H-M   P21/c

loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'

_cell_length_a                   9.4415(3)
_cell_length_b                   8.0573(3)
_cell_length_c                   8.1969(3)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.410(2)
_cell_angle_gamma                90.00
_cell_volume                     623.55(4)
_cell_formula_units_Z            2
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    8384
_cell_measurement_theta_min      4.2
_cell_measurement_theta_max      35.19

_exptl_crystal_description       plate
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.50
_exptl_crystal_size_mid          0.50
_exptl_crystal_size_min          0.20
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.675
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             324
_exptl_absorpt_coefficient_mu    0.750
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.7056
_exptl_absorpt_correction_T_max  0.8645
_exptl_absorpt_process_details   'Bruker SHELXTL'

_exptl_special_details           
;
?
;

_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Bruker Kappa Apex2 CCD'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            8384
_diffrn_reflns_av_R_equivalents  0.0281
_diffrn_reflns_av_sigmaI/netI    0.0150
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_theta_min         3.32
_diffrn_reflns_theta_max         26.02
_reflns_number_total             1217
_reflns_number_gt                1194
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Bruker Apex2'
_computing_cell_refinement       'Bruker Apex2'
_computing_data_reduction        'Bruker Apex2'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'

_refine_special_details          
;
Refinement of F^2^ against ALL reflections. The weighted R-factor wR and
goodness of fit S are based on F^2^, conventional R-factors R are based
on F, with F set to zero for negative F^2^. The threshold expression of
F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is
not relevant to the choice of reflections for refinement. R-factors based
on F^2^ are statistically about twice as large as those based on F, and R-
factors based on ALL data will be even larger.
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[\s^2^(Fo^2^)+(0.0000P)^2^+2.3105P] where P=(Fo^2^+2Fc^2^)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         1217
_refine_ls_number_parameters     114
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0636
_refine_ls_R_factor_gt           0.0628
_refine_ls_wR_factor_ref         0.1304
_refine_ls_wR_factor_gt          0.1300
_refine_ls_goodness_of_fit_ref   1.373
_refine_ls_restrained_S_all      1.373
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

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 0.31634(11) 0.61517(14) -0.12335(14) 0.0302(3) Uani 1 1 d . A .
S2 S 0.0850(4) 0.4774(5) 0.3122(5) 0.0295(12) Uani 0.496(11) 1 d P A 1
O1 O 0.4163(19) 0.398(2) 0.295(2) 0.035(5) Uiso 0.496(11) 1 d P A 1
S2A S 0.4212(7) 0.3793(9) 0.3196(8) 0.0422(14) Uani 0.504(11) 1 d P A 2
O1A O 0.1069(11) 0.5161(14) 0.2524(16) 0.038(2) Uani 0.504(11) 1 d P A 2
C1 C 0.1738(5) 0.6027(6) 0.0041(6) 0.0348(11) Uani 1 1 d . A .
H1 H 0.0824 0.6445 -0.0222 0.042 Uiso 1 1 calc R . .
C2 C 0.2064(4) 0.5266(5) 0.1465(5) 0.0282(9) Uani 1 1 d . . .
C3 C 0.3517(4) 0.4792(5) 0.1567(5) 0.0260(9) Uani 1 1 d . A .
C4 C 0.4260(4) 0.5156(5) 0.0174(5) 0.0203(8) Uani 1 1 d . . .
C5 C 0.1981(17) 0.3477(17) 0.4406(16) 0.040(3) Uani 0.496(11) 1 d P A 1
H5A H 0.1597 0.3450 0.5526 0.048 Uiso 0.496(11) 1 calc PR A 1
H5B H 0.1980 0.2328 0.3977 0.048 Uiso 0.496(11) 1 calc PR A 1
C6 C 0.3461(14) 0.4118(19) 0.4455(17) 0.039(3) Uani 0.496(11) 1 d P A 1
H6A H 0.3445 0.5298 0.4788 0.046 Uiso 0.496(11) 1 calc PR A 1
H6B H 0.4004 0.3495 0.5291 0.046 Uiso 0.496(11) 1 calc PR A 1
C5A C 0.1367(18) 0.3826(16) 0.370(2) 0.054(4) Uani 0.504(11) 1 d P A 2
H5C H 0.1410 0.2750 0.3124 0.065 Uiso 0.504(11) 1 calc PR A 2
H5D H 0.0589 0.3766 0.4506 0.065 Uiso 0.504(11) 1 calc PR A 2
C6A C 0.273(2) 0.4119(18) 0.4578(15) 0.045(4) Uani 0.504(11) 1 d P A 2
H6C H 0.2814 0.3350 0.5516 0.054 Uiso 0.504(11) 1 calc PR A 2
H6D H 0.2758 0.5269 0.5003 0.054 Uiso 0.504(11) 1 calc PR A 2

loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
S1 0.0267(5) 0.0304(6) 0.0332(6) 0.0020(5) -0.0083(4) 0.0062(4)
S2 0.0256(15) 0.032(2) 0.031(2) -0.0012(15) 0.0041(13) 0.0021(13)
S2A 0.050(2) 0.045(2) 0.032(2) 0.0100(18) 0.0131(16) 0.0116(16)
O1A 0.039(5) 0.035(5) 0.040(6) -0.005(4) 0.015(4) -0.010(4)
C1 0.023(2) 0.032(2) 0.049(3) -0.009(2) -0.0062(19) 0.0041(18)
C2 0.026(2) 0.021(2) 0.037(2) -0.0105(18) 0.0038(18) -0.0022(17)
C3 0.030(2) 0.019(2) 0.030(2) -0.0039(16) -0.0026(17) 0.0000(17)
C4 0.0192(19) 0.0191(19) 0.0226(19) -0.0003(15) -0.0026(14) 0.0001(15)
C5 0.054(9) 0.029(7) 0.036(6) 0.004(5) 0.004(6) -0.002(7)
C6 0.034(6) 0.040(6) 0.042(7) 0.014(5) -0.003(6) -0.017(7)
C5A 0.066(10) 0.029(7) 0.068(10) 0.002(8) 0.046(8) -0.004(8)
C6A 0.073(11) 0.033(7) 0.029(6) 0.014(5) 0.011(9) -0.021(10)

_geom_special_details            
;
All esds (except the esd in the dihedral angle between two l.s. planes)
are estimated using the full covariance matrix. The cell esds are taken
into account individually in the estimation of esds in distances, angles
and torsion angles; correlations between esds in cell parameters are only
used when they are defined by crystal symmetry. An approximate (isotropic)
treatment of cell esds is used for estimating esds involving l.s. planes.
;

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 C1 1.712(5) . ?
S1 C4 1.741(4) . ?
S2 C5 1.823(14) . ?
S2 C2 1.827(6) . ?
O1 C6 1.41(2) . ?
O1 C3 1.436(16) . ?
S2A C3 1.688(8) . ?
S2A C6A 1.824(18) . ?
O1A C2 1.286(13) . ?
O1A C5A 1.472(19) . ?
C1 C2 1.352(7) . ?
C1 H1 0.9500 . ?
C2 C3 1.426(6) . ?
C3 C4 1.376(6) . ?
C4 C4 1.450(7) 3_665 ?
C5 C6 1.491(16) . ?
C5 H5A 0.9900 . ?
C5 H5B 0.9900 . ?
C6 H6A 0.9900 . ?
C6 H6B 0.9900 . ?
C5A C6A 1.49(2) . ?
C5A H5C 0.9900 . ?
C5A H5D 0.9900 . ?
C6A H6C 0.9900 . ?
C6A H6D 0.9900 . ?

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
C1 S1 C4 92.0(2) . . ?
C5 S2 C2 100.7(5) . . ?
C6 O1 C3 117.1(14) . . ?
C3 S2A C6A 97.3(6) . . ?
C2 O1A C5A 110.7(8) . . ?
C2 C1 S1 112.3(3) . . ?
C2 C1 H1 123.9 . . ?
S1 C1 H1 123.9 . . ?
O1A C2 C1 116.7(7) . . ?
O1A C2 C3 130.5(7) . . ?
C1 C2 C3 112.6(4) . . ?
C1 C2 S2 126.9(3) . . ?
C3 C2 S2 120.5(4) . . ?
C4 C3 C2 113.0(4) . . ?
C4 C3 O1 122.2(8) . . ?
C2 C3 O1 124.8(8) . . ?
C4 C3 S2A 124.1(4) . . ?
C2 C3 S2A 122.8(4) . . ?
C3 C4 C4 128.6(4) . 3_665 ?
C3 C4 S1 110.1(3) . . ?
C4 C4 S1 121.2(4) 3_665 . ?
C6 C5 S2 111.2(10) . . ?
C6 C5 H5A 109.4 . . ?
S2 C5 H5A 109.4 . . ?
C6 C5 H5B 109.4 . . ?
S2 C5 H5B 109.4 . . ?
H5A C5 H5B 108.0 . . ?
O1 C6 C5 113.3(13) . . ?
O1 C6 H6A 108.9 . . ?
C5 C6 H6A 108.9 . . ?
O1 C6 H6B 108.9 . . ?
C5 C6 H6B 108.9 . . ?
H6A C6 H6B 107.7 . . ?
O1A C5A C6A 111.2(10) . . ?
O1A C5A H5C 109.4 . . ?
C6A C5A H5C 109.4 . . ?
O1A C5A H5D 109.4 . . ?
C6A C5A H5D 109.4 . . ?
H5C C5A H5D 108.0 . . ?
C5A C6A S2A 110.0(9) . . ?
C5A C6A H6C 109.7 . . ?
S2A C6A H6C 109.7 . . ?
C5A C6A H6D 109.7 . . ?
S2A C6A H6D 109.7 . . ?
H6C C6A H6D 108.2 . . ?

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
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C4 S1 C1 C2 -0.2(4) . . . . ?
C5A O1A C2 C1 159.1(8) . . . . ?
C5A O1A C2 C3 -25.1(13) . . . . ?
C5A O1A C2 S2 3(2) . . . . ?
S1 C1 C2 O1A 177.9(6) . . . . ?
S1 C1 C2 C3 1.4(5) . . . . ?
S1 C1 C2 S2 -176.6(3) . . . . ?
C5 S2 C2 O1A -163(3) . . . . ?
C5 S2 C2 C1 170.7(6) . . . . ?
C5 S2 C2 C3 -7.1(6) . . . . ?
O1A C2 C3 C4 -178.1(7) . . . . ?
C1 C2 C3 C4 -2.2(5) . . . . ?
S2 C2 C3 C4 175.9(3) . . . . ?
O1A C2 C3 O1 3.2(13) . . . . ?
C1 C2 C3 O1 179.1(9) . . . . ?
S2 C2 C3 O1 -2.8(10) . . . . ?
O1A C2 C3 S2A 5.1(9) . . . . ?
C1 C2 C3 S2A -179.0(4) . . . . ?
S2 C2 C3 S2A -1.0(6) . . . . ?
C6 O1 C3 C4 161.3(11) . . . . ?
C6 O1 C3 C2 -20.2(19) . . . . ?
C6 O1 C3 S2A -59(22) . . . . ?
C6A S2A C3 C4 170.7(6) . . . . ?
C6A S2A C3 C2 -12.9(7) . . . . ?
C6A S2A C3 O1 129(22) . . . . ?
C2 C3 C4 C4 -179.3(5) . . . 3_665 ?
O1 C3 C4 C4 -0.6(11) . . . 3_665 ?
S2A C3 C4 C4 -2.5(8) . . . 3_665 ?
C2 C3 C4 S1 2.0(4) . . . . ?
O1 C3 C4 S1 -179.3(9) . . . . ?
S2A C3 C4 S1 178.8(4) . . . . ?
C1 S1 C4 C3 -1.1(3) . . . . ?
C1 S1 C4 C4 -179.9(5) . . . 3_665 ?
C2 S2 C5 C6 38.6(10) . . . . ?
C3 O1 C6 C5 57.7(19) . . . . ?
S2 C5 C6 O1 -67.4(15) . . . . ?
C2 O1A C5A C6A 59.1(13) . . . . ?
O1A C5A C6A S2A -71.2(12) . . . . ?
C3 S2A C6A C5A 43.2(11) . . . . ?

_diffrn_measured_fraction_theta_max 0.990
_diffrn_reflns_theta_full        26.02
_diffrn_measured_fraction_theta_full 0.990
_refine_diff_density_max         0.335
_refine_diff_density_min         -0.408
_refine_diff_density_rms         0.080