# Supplementary Material (ESI) for Journal of Materials Chemistry
# This journal is (C) The Royal Society of Chemistry 2009

data_global
_journal_name_full               J.Mater.Chem.

_journal_coden_Cambridge         1145

_publ_contact_author_name        'Clara Santato'
_publ_contact_author_email       CLARA.SANTATO@POLYMTL.CA

_publ_section_title              
;
Influence of the oxidation level on the electronic,
morphological and charge transport properties of novel
dithienothiophene-S-oxide and -S,S-dioxide inner core oligomers
;
_publ_author_name                'Clara Santato'

data_red_0m
_database_code_depnum_ccdc_archive 'CCDC 741027'
_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C30 H36 O2 S5'
_chemical_formula_weight         588.89
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           Triclinic
_symmetry_space_group_name_H-M   P-1
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'
_cell_length_a                   9.2754(15)
_cell_length_b                   11.6067(19)
_cell_length_c                   14.374(2)
_cell_angle_alpha                80.407(2)
_cell_angle_beta                 87.018(2)
_cell_angle_gamma                88.813(2)
_cell_volume                     1523.7(4)
_cell_formula_units_Z            2
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    ?
_cell_measurement_theta_min      ?
_cell_measurement_theta_max      ?
_exptl_crystal_description       Needle
_exptl_crystal_colour            red
_exptl_crystal_size_max          0.200
_exptl_crystal_size_mid          0.06
_exptl_crystal_size_min          0.05
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.284
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             624
_exptl_absorpt_coefficient_mu    0.406
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_correction_T_min  0.922
_exptl_absorpt_correction_T_max  0.976
_exptl_absorpt_process_details   SADABS
_exptl_special_details           
;
?
;
_diffrn_ambient_temperature      296(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  ?
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            16795
_diffrn_reflns_av_R_equivalents  0.0359
_diffrn_reflns_av_sigmaI/netI    0.0581
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_theta_min         1.44
_diffrn_reflns_theta_max         28.56
_reflns_number_total             7060
_reflns_number_gt                3156
_reflns_threshold_expression     >2sigma(I)
_computing_data_collection       SMART
_computing_cell_refinement       SMART
_computing_data_reduction        SAINT
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    'SCHAKAL99 (Keller 1999)'
_computing_publication_material  'SHELXL-97 (Sheldrick, 1997)'
_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 Rfactors
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^)+(0.0830P)^2^+0.3846P] 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    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         7060
_refine_ls_number_parameters     338
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.1439
_refine_ls_R_factor_gt           0.0604
_refine_ls_wR_factor_ref         0.1924
_refine_ls_wR_factor_gt          0.1481
_refine_ls_goodness_of_fit_ref   1.003
_refine_ls_restrained_S_all      1.015
_refine_ls_shift/su_max          0.012
_refine_ls_shift/su_mean         0.001
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 0.62245(10) 0.33743(8) 1.00884(7) 0.0686(3) Uani 1 1 d . . .
S2 S 0.86500(11) 0.53403(9) 1.12365(7) 0.0691(3) Uani 1 1 d . . .
S3 S 0.75987(11) 0.64842(9) 0.84732(7) 0.0718(3) Uani 1 1 d . . .
S4 S 1.11950(13) 0.84195(11) 1.14080(9) 0.0935(4) Uani 1 1 d . . .
S5 S 0.38908(12) 0.23001(11) 0.78176(9) 0.0885(4) Uani 1 1 d . . .
O1 O 0.6559(3) 0.7415(2) 0.8315(2) 0.0887(8) Uani 1 1 d . . .
O2 O 0.8694(3) 0.6422(3) 0.77418(19) 0.0873(8) Uani 1 1 d . . .
C10 C 1.0341(4) 0.7102(4) 1.1597(3) 0.0743(11) Uani 1 1 d . . .
C7 C 1.1816(5) 0.8222(5) 1.2517(4) 0.0979(15) Uani 1 1 d . . .
C4 C 1.2772(5) 1.0672(4) 1.3882(3) 0.1037(15) Uani 1 1 d . . .
H4A H 1.3415 1.0200 1.4307 0.124 Uiso 1 1 calc R . .
H4B H 1.3365 1.1136 1.3388 0.124 Uiso 1 1 calc R . .
C5 C 1.1848(5) 0.9864(4) 1.3436(4) 0.0997(14) Uani 1 1 d . . .
H5A H 1.1303 0.9362 1.3933 0.120 Uiso 1 1 calc R . .
H5B H 1.1162 1.0333 1.3043 0.120 Uiso 1 1 calc R . .
C9 C 1.0562(6) 0.6558(5) 1.2470(4) 0.1101(16) Uani 1 1 d . . .
H9 H 1.0191 0.5825 1.2714 0.132 Uiso 1 1 calc R . .
C3 C 1.1941(7) 1.1458(5) 1.4408(4) 0.1265(19) Uani 1 1 d . . .
H3A H 1.1384 1.0997 1.4922 0.152 Uiso 1 1 calc R . .
H3B H 1.1266 1.1907 1.3992 0.152 Uiso 1 1 calc R . .
C6 C 1.2686(5) 0.9131(5) 1.2859(4) 0.1153(18) Uani 1 1 d . . .
H6A H 1.3456 0.8743 1.3228 0.138 Uiso 1 1 calc R . .
H6B H 1.3130 0.9631 1.2316 0.138 Uiso 1 1 calc R . .
C8 C 1.1398(6) 0.7182(6) 1.2986(4) 0.1185(18) Uani 1 1 d . . .
H8 H 1.1642 0.6899 1.3603 0.142 Uiso 1 1 calc R . .
C2 C 1.2893(9) 1.2303(6) 1.4812(5) 0.164(3) Uani 1 1 d . . .
H2A H 1.3498 1.1857 1.5276 0.196 Uiso 1 1 calc R . .
H2B H 1.3522 1.2706 1.4306 0.196 Uiso 1 1 calc R . .
C1 C 1.2076(11) 1.3156(8) 1.5248(7) 0.244(5) Uani 1 1 d . . .
H1A H 1.1471 1.3601 1.4793 0.366 Uiso 1 1 calc R . .
H1B H 1.2726 1.3671 1.5471 0.366 Uiso 1 1 calc R . .
H1C H 1.1487 1.2766 1.5770 0.366 Uiso 1 1 calc R . .
C15 C 0.7949(3) 0.5427(3) 1.0167(3) 0.0612(9) Uani 1 1 d . . .
C12 C 0.8346(4) 0.6416(3) 0.9578(3) 0.0657(9) Uani 1 1 d . . .
C16 C 0.6752(4) 0.5121(3) 0.8827(3) 0.0647(9) Uani 1 1 d . . .
C18 C 0.5859(4) 0.4430(3) 0.8383(3) 0.0674(10) Uani 1 1 d . . .
C17 C 0.5472(4) 0.3430(3) 0.9002(3) 0.0649(9) Uani 1 1 d . . .
C13 C 0.9240(4) 0.7156(3) 0.9979(3) 0.0683(10) Uani 1 1 d . . .
C11 C 0.9508(4) 0.6679(3) 1.0889(3) 0.0664(10) Uani 1 1 d . . .
C20 C 0.4591(4) 0.2450(3) 0.8873(3) 0.0706(10) Uani 1 1 d . . .
C19 C 0.5415(5) 0.4769(4) 0.7391(3) 0.0979(14) Uani 1 1 d . . .
H19A H 0.5873 0.4254 0.7004 0.147 Uiso 1 1 calc R . .
H19B H 0.5700 0.5558 0.7155 0.147 Uiso 1 1 calc R . .
H19C H 0.4386 0.4712 0.7375 0.147 Uiso 1 1 calc R . .
C14 C 0.9802(5) 0.8291(4) 0.9441(3) 0.0964(14) Uani 1 1 d . . .
H14A H 0.9514 0.8915 0.9774 0.145 Uiso 1 1 calc R . .
H14B H 0.9416 0.8432 0.8825 0.145 Uiso 1 1 calc R . .
H14C H 1.0837 0.8251 0.9379 0.145 Uiso 1 1 calc R . .
C23 C 0.3118(5) 0.0992(4) 0.8278(4) 0.0878(13) Uani 1 1 d . . .
C21 C 0.4199(5) 0.1525(4) 0.9539(3) 0.0900(13) Uani 1 1 d . . .
H21 H 0.4446 0.1442 1.0165 0.108 Uiso 1 1 calc R . .
C24 C 0.2311(5) 0.0328(4) 0.7666(4) 0.1064(16) Uani 1 1 d . . .
H24A H 0.1412 0.0061 0.8000 0.128 Uiso 1 1 calc R . .
H24B H 0.2071 0.0857 0.7098 0.128 Uiso 1 1 calc R . .
C22 C 0.3379(5) 0.0704(4) 0.9185(4) 0.0972(14) Uani 1 1 d . . .
H22 H 0.3048 0.0017 0.9555 0.117 Uiso 1 1 calc R . .
C25 C 0.3096(6) -0.0685(5) 0.7392(4) 0.1212(19) Uani 1 1 d . . .
H25A H 0.3357 -0.1202 0.7962 0.145 Uiso 1 1 calc R . .
H25B H 0.3985 -0.0412 0.7048 0.145 Uiso 1 1 calc R . .
C26 C 0.2292(6) -0.1382(5) 0.6794(4) 0.1243(19) Uani 1 1 d . . .
H26A H 0.1398 -0.1639 0.7139 0.149 Uiso 1 1 calc R . .
H26B H 0.2035 -0.0858 0.6227 0.149 Uiso 1 1 calc R . .
C27 C 0.2976(9) -0.2361(7) 0.6515(7) 0.235(5) Uani 1 1 d . . .
H27A H 0.3231 -0.2892 0.7079 0.282 Uiso 1 1 calc R . .
H27B H 0.3868 -0.2110 0.6165 0.282 Uiso 1 1 calc R . .
C28 C 0.2117(9) -0.3036(8) 0.5913(6) 0.204(4) Uani 1 1 d D . .
H28A H 0.1330 -0.3430 0.6303 0.245 Uiso 1 1 calc R . .
H28B H 0.1696 -0.2485 0.5414 0.245 Uiso 1 1 calc R . .
C29 C 0.2942(14) -0.3867(10) 0.5504(8) 0.350(9) Uani 1 1 d D . .
H29A H 0.3845 -0.3531 0.5250 0.525 Uiso 1 1 calc R . .
H29B H 0.2425 -0.4102 0.5007 0.525 Uiso 1 1 calc R . .
H29C H 0.3120 -0.4536 0.5977 0.525 Uiso 1 1 calc R . .
C30 C 0.7041(4) 0.4677(3) 0.9721(3) 0.0619(9) Uani 1 1 d . . .
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 0.0724(6) 0.0608(6) 0.0722(6) -0.0095(5) -0.0032(5) 0.0003(5)
S2 0.0729(6) 0.0684(6) 0.0664(6) -0.0121(5) -0.0038(5) 0.0017(5)
S3 0.0719(6) 0.0695(6) 0.0708(7) -0.0021(5) -0.0044(5) -0.0009(5)
S4 0.0863(8) 0.0956(9) 0.1047(9) -0.0336(7) -0.0017(6) -0.0170(6)
S5 0.0867(8) 0.0883(8) 0.0952(8) -0.0257(6) -0.0133(6) -0.0063(6)
O1 0.0860(19) 0.0740(18) 0.099(2) 0.0065(15) -0.0129(16) 0.0115(15)
O2 0.0854(18) 0.099(2) 0.0720(18) -0.0011(15) 0.0052(15) -0.0065(16)
C10 0.066(2) 0.082(3) 0.080(3) -0.030(2) -0.001(2) 0.004(2)
C7 0.076(3) 0.123(4) 0.106(4) -0.053(3) 0.002(3) -0.004(3)
C4 0.118(4) 0.109(4) 0.089(3) -0.030(3) -0.003(3) -0.022(3)
C5 0.093(3) 0.105(4) 0.109(4) -0.040(3) 0.001(3) -0.008(3)
C9 0.143(4) 0.105(4) 0.086(4) -0.015(3) -0.031(3) -0.030(3)
C3 0.161(5) 0.119(4) 0.105(4) -0.035(4) -0.003(4) -0.022(4)
C6 0.082(3) 0.146(5) 0.135(5) -0.069(4) 0.000(3) -0.018(3)
C8 0.141(5) 0.136(5) 0.087(4) -0.032(3) -0.037(3) -0.018(4)
C2 0.220(7) 0.145(6) 0.144(6) -0.073(5) -0.001(5) -0.023(5)
C1 0.318(13) 0.204(9) 0.243(11) -0.117(9) -0.062(9) 0.010(9)
C15 0.056(2) 0.061(2) 0.067(2) -0.0139(19) 0.0001(17) 0.0066(17)
C12 0.064(2) 0.060(2) 0.072(2) -0.0089(19) 0.0033(18) 0.0024(18)
C16 0.066(2) 0.063(2) 0.065(2) -0.0073(18) -0.0056(18) 0.0049(18)
C18 0.058(2) 0.072(3) 0.072(3) -0.013(2) -0.0057(19) 0.0084(19)
C17 0.059(2) 0.060(2) 0.077(3) -0.016(2) -0.0025(18) 0.0053(18)
C13 0.060(2) 0.065(2) 0.081(3) -0.016(2) 0.004(2) -0.0010(18)
C11 0.060(2) 0.067(2) 0.074(3) -0.019(2) 0.0035(19) 0.0067(18)
C20 0.057(2) 0.068(3) 0.090(3) -0.025(2) -0.001(2) 0.0071(19)
C19 0.105(3) 0.101(3) 0.086(3) -0.001(3) -0.025(3) -0.012(3)
C14 0.109(3) 0.085(3) 0.092(3) -0.002(2) -0.007(3) -0.026(3)
C23 0.075(3) 0.083(3) 0.112(4) -0.035(3) -0.008(3) -0.003(2)
C21 0.100(3) 0.079(3) 0.093(3) -0.015(3) -0.008(3) -0.016(3)
C24 0.095(3) 0.099(4) 0.134(4) -0.042(3) -0.008(3) -0.019(3)
C22 0.102(3) 0.075(3) 0.116(4) -0.014(3) -0.010(3) -0.019(3)
C25 0.111(4) 0.116(4) 0.156(5) -0.075(4) -0.025(4) 0.009(3)
C26 0.125(4) 0.125(5) 0.137(5) -0.056(4) -0.017(4) -0.007(4)
C27 0.243(9) 0.192(8) 0.327(12) -0.181(9) -0.144(9) 0.092(7)
C28 0.256(9) 0.173(7) 0.223(9) -0.123(7) -0.107(7) 0.052(7)
C29 0.54(2) 0.256(13) 0.306(15) -0.142(12) -0.290(16) 0.128(14)
C30 0.056(2) 0.059(2) 0.071(3) -0.0135(19) 0.0006(18) 0.0069(17)
_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 C30 1.696(4) . ?
S1 C17 1.735(4) . ?
S2 C15 1.687(4) . ?
S2 C11 1.746(4) . ?
S3 O1 1.431(3) . ?
S3 O2 1.433(3) . ?
S3 C12 1.755(4) . ?
S3 C16 1.766(4) . ?
S4 C7 1.701(5) . ?
S4 C10 1.712(4) . ?
S5 C23 1.708(5) . ?
S5 C20 1.717(4) . ?
C10 C9 1.332(6) . ?
C10 C11 1.462(5) . ?
C7 C8 1.336(7) . ?
C7 C6 1.502(6) . ?
C4 C3 1.462(6) . ?
C4 C5 1.522(6) . ?
C5 C6 1.468(6) . ?
C9 C8 1.392(7) . ?
C3 C2 1.536(8) . ?
C2 C1 1.440(9) . ?
C15 C12 1.353(5) . ?
C15 C30 1.466(5) . ?
C12 C13 1.414(5) . ?
C16 C30 1.341(5) . ?
C16 C18 1.411(5) . ?
C18 C17 1.381(5) . ?
C18 C19 1.492(5) . ?
C17 C20 1.456(5) . ?
C13 C11 1.366(5) . ?
C13 C14 1.500(5) . ?
C20 C21 1.356(6) . ?
C23 C22 1.323(6) . ?
C23 C24 1.499(6) . ?
C21 C22 1.406(6) . ?
C24 C25 1.468(6) . ?
C25 C26 1.508(6) . ?
C26 C27 1.395(7) . ?
C27 C28 1.524(9) . ?
C28 C29 1.405(8) . ?
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
C30 S1 C17 91.35(18) . . ?
C15 S2 C11 91.25(19) . . ?
O1 S3 O2 117.31(17) . . ?
O1 S3 C12 110.92(18) . . ?
O2 S3 C12 111.50(17) . . ?
O1 S3 C16 111.30(17) . . ?
O2 S3 C16 111.08(18) . . ?
C12 S3 C16 91.93(18) . . ?
C7 S4 C10 93.2(3) . . ?
C23 S5 C20 92.9(2) . . ?
C9 C10 C11 127.1(4) . . ?
C9 C10 S4 109.2(3) . . ?
C11 C10 S4 123.7(3) . . ?
C8 C7 C6 128.4(5) . . ?
C8 C7 S4 109.5(4) . . ?
C6 C7 S4 122.1(5) . . ?
C3 C4 C5 114.0(4) . . ?
C6 C5 C4 113.6(4) . . ?
C10 C9 C8 114.2(5) . . ?
C4 C3 C2 113.0(5) . . ?
C5 C6 C7 114.2(4) . . ?
C7 C8 C9 114.0(5) . . ?
C1 C2 C3 113.2(7) . . ?
C12 C15 C30 112.8(3) . . ?
C12 C15 S2 112.0(3) . . ?
C30 C15 S2 135.2(3) . . ?
C15 C12 C13 114.5(4) . . ?
C15 C12 S3 110.9(3) . . ?
C13 C12 S3 134.6(3) . . ?
C30 C16 C18 115.2(4) . . ?
C30 C16 S3 110.6(3) . . ?
C18 C16 S3 134.3(3) . . ?
C17 C18 C16 110.0(3) . . ?
C17 C18 C19 126.6(4) . . ?
C16 C18 C19 123.4(4) . . ?
C18 C17 C20 130.7(4) . . ?
C18 C17 S1 111.8(3) . . ?
C20 C17 S1 117.6(3) . . ?
C11 C13 C12 110.5(4) . . ?
C11 C13 C14 126.8(4) . . ?
C12 C13 C14 122.7(4) . . ?
C13 C11 C10 131.5(4) . . ?
C13 C11 S2 111.8(3) . . ?
C10 C11 S2 116.7(3) . . ?
C21 C20 C17 126.8(4) . . ?
C21 C20 S5 109.4(3) . . ?
C17 C20 S5 123.8(3) . . ?
C22 C23 C24 129.0(5) . . ?
C22 C23 S5 110.4(4) . . ?
C24 C23 S5 120.6(4) . . ?
C20 C21 C22 113.1(4) . . ?
C25 C24 C23 114.7(4) . . ?
C23 C22 C21 114.3(5) . . ?
C24 C25 C26 115.7(4) . . ?
C27 C26 C25 118.4(5) . . ?
C26 C27 C28 116.3(6) . . ?
C29 C28 C27 113.8(8) . . ?
C16 C30 C15 113.7(3) . . ?
C16 C30 S1 111.7(3) . . ?
C15 C30 S1 134.5(3) . . ?
_diffrn_measured_fraction_theta_max 0.906
_diffrn_reflns_theta_full        28.56
_diffrn_measured_fraction_theta_full 0.906
_refine_diff_density_max         0.364
_refine_diff_density_min         -0.242
_refine_diff_density_rms         0.055