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

data_global
_journal_name_full               J.Mater.Chem.

_journal_coden_Cambridge         1145
_journal_volume                  ?
_journal_page_first              ?
_journal_year                    ?

_publ_contact_author_name        'Roncali, J.'
_publ_contact_author_email       Jean.Roncali@univ-angers.fr

_publ_section_title              
;
Electropolymerizable 3D \"I-Conjugated Architectures
with Ethylenedioxythiophene (EDOT) End-groups as Precursors
of Electroactive Conjugated Networks
;
_publ_author_name                J.Roncali

# Attachment '- FP72cifdoc.cif'

data_fp72
_database_code_depnum_ccdc_archive 'CCDC 773448'
#TrackingRef '- FP72cifdoc.cif'

_audit_creation_date             2008-12-09T16:20:42-00:00
_audit_creation_method           'WinGX routine CIF_UPDATE'

#------------------ CHEMICAL INFORMATION ------------------------------------#

_chemical_formula_moiety         'C24 H14 S6'
_chemical_formula_sum            'C24 H14 S6'
_chemical_formula_weight         494.71
_chemical_absolute_configuration ad

#------------------ UNIT CELL INFORMATION -----------------------------------#

_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   'P 1 21 1'
_symmetry_space_group_name_Hall  'P 2yb'
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y+1/2, -z'

_cell_length_a                   12.010(1)
_cell_length_b                   6.0745(4)
_cell_length_c                   15.626(2)
_cell_angle_alpha                90
_cell_angle_beta                 104.14(1)
_cell_angle_gamma                90
_cell_volume                     1105.48(18)
_cell_formula_units_Z            2
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    8000
_cell_measurement_theta_min      1.8
_cell_measurement_theta_max      26

#------------------ CRYSTAL INFORMATION -------------------------------------#

_exptl_crystal_description       prism
_exptl_crystal_colour            yellow
_exptl_crystal_size_max          0.62
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.08
_exptl_crystal_density_diffrn    1.486
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             508
_exptl_absorpt_coefficient_mu    0.629
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_correction_T_min  0.8066
_exptl_absorpt_correction_T_max  0.9558
_exptl_absorpt_process_details   
;
PLATON-ABSGAUSS : Spek, A.L. (2003), J.Appl.Cryst. 36, 7-13
;

#------------------ DATA COLLECTION INFORMATION -----------------------------#

_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_probe          x-ray
_diffrn_measurement_device_type  'STOE IPDS'
_diffrn_measurement_method       'Oscillation Phi Incr 1.5 deg'
_diffrn_detector_area_resol_mean 6.66
_diffrn_reflns_number            15744
_diffrn_reflns_av_R_equivalents  0.0745
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_theta_min         1.75
_diffrn_reflns_theta_max         26.04
_diffrn_reflns_theta_full        26.04
_diffrn_measured_fraction_theta_max 0.985
_diffrn_measured_fraction_theta_full 0.985
_reflns_number_total             4289
_reflns_number_gt                3147
_reflns_threshold_expression     >2sigma(I)

#------------------ COMPUTER PROGRAMS USED ----------------------------------#

_computing_data_collection       'EXPOSE, STOE IPDS'
_computing_cell_refinement       'SELECT,CELL, STOE IPDS'
_computing_data_reduction        'INTEGRATE, STOE IPDS'
_computing_structure_solution    'Direct methods (Sir92,Altomare et al.,1993)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    'DIAMOND 3.1f (Crystal Impact GbR 2005)'
_computing_publication_material  'WinGX publication routines (Farrugia, 1999)'

#------------------ REFINEMENT INFORMATION ----------------------------------#

_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^)+(0.0910P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_number_reflns         4289
_refine_ls_number_parameters     309
_refine_ls_number_restraints     6
_refine_ls_R_factor_gt           0.0462
_refine_ls_wR_factor_ref         0.1424
_refine_ls_goodness_of_fit_ref   1.022
_refine_ls_restrained_S_all      1.022
_refine_ls_shift/su_max          0
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.06(12)
_refine_diff_density_max         0.421
_refine_diff_density_min         -0.434

#------------------ ATOMIC TYPES, COORDINATES AND THERMAL PARAMETERS --------#

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 0 '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_
_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_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_group
_atom_site_disorder_assembly
C1 C -0.2046(4) 0.9524(12) 0.9318(4) 0.0747(17) Uani 1 d . . .
H1 H -0.2694 0.9909 0.951 0.09 Uiso 1 calc R . .
C2 C -0.1493(4) 0.7682(12) 0.9545(4) 0.0737(18) Uani 1 d . . .
H2 H -0.1718 0.6673 0.9918 0.088 Uiso 1 calc R . .
C3 C -0.0472(3) 0.7286(10) 0.9171(3) 0.0571(13) Uani 1 d . . .
H3 H 0.0014 0.6072 0.9244 0.068 Uiso 1 calc R . .
C4 C -0.0433(4) 0.9316(9) 0.8657(3) 0.0530(12) Uani 1 d . . .
C5 C 0.0433(3) 0.9779(8) 0.8159(3) 0.0495(11) Uani 1 d . . .
C6 C 0.0360(3) 1.1249(9) 0.7496(3) 0.0484(10) Uani 1 d . . .
H6 H -0.028 1.214 0.729 0.058 Uiso 1 calc R . .
C7 C 0.1346(3) 1.1318(8) 0.7138(3) 0.0450(10) Uani 1 d . . B
C8 C 0.2165(3) 0.9838(7) 0.7559(3) 0.0439(10) Uani 1 d . . .
C9 C 0.3302(3) 0.9387(7) 0.7401(3) 0.0414(9) Uani 1 d . . A
C10 C 0.4312(3) 1.0575(7) 0.7700(3) 0.0416(9) Uani 1 d . . .
C11 C 0.5226(3) 0.9599(8) 0.7391(3) 0.0458(10) Uani 1 d . . .
H11 H 0.5962 1.0189 0.7507 0.055 Uiso 1 calc R . .
C12 C 0.4923(4) 0.7748(8) 0.6917(3) 0.0457(10) Uani 1 d . . A
C13 C 0.5665(4) 0.6305(9) 0.6539(3) 0.0529(11) Uani 1 d . . .
C14 C 0.536(3) 0.435(9) 0.602(3) 0.102(15) Uani 0.650(9) d PD 1 A
H14 H 0.4626 0.3725 0.5858 0.122 Uiso 0.650(9) calc PR 1 A
C15 C 0.6397(6) 0.3495(13) 0.5799(4) 0.090(2) Uani 1 d D . .
H15A H 0.64 0.2341 0.5408 0.108 Uiso 0.650(9) calc PR 1 A
H15B H 0.6471 0.221 0.5494 0.108 Uiso 0.350(9) d PR 2 A
C16 C 0.7317(5) 0.4555(13) 0.6215(5) 0.085(2) Uani 1 d D . A
H16A H 0.8046 0.4129 0.6173 0.103 Uiso 0.650(9) calc PR 1 A
H16B H 0.8066 0.4356 0.6164 0.103 Uiso 0.350(9) d PR 2 A
C17 C 0.6844(17) 0.650(5) 0.659(2) 0.093(14) Uani 0.350(9) d PD 2 A
H17 H 0.7282 0.7715 0.6822 0.112 Uiso 0.350(9) calc PR 2 A
C18 C 0.1405(3) 1.2748(8) 0.6389(3) 0.0468(10) Uani 1 d D . .
C19 C 0.083(4) 1.466(5) 0.611(2) 0.059(12) Uani 0.318(8) d PD 4 B
H19 H 0.035 1.5313 0.6426 0.071 Uiso 0.318(8) calc PR 4 B
C20 C 0.1011(4) 1.5646(10) 0.5300(4) 0.0676(15) Uani 1 d D . .
H20A H 0.0756 1.6891 0.4962 0.081 Uiso 0.682(8) calc PR 3 B
H20B H 0.0776 1.6959 0.5005 0.081 Uiso 0.318(8) d PR 4 B
C21 C 0.1691(5) 1.4149(10) 0.5060(3) 0.0664(15) Uani 1 d D . B
H21A H 0.1981 1.4247 0.4561 0.08 Uiso 0.682(8) calc PR 3 B
H21B H 0.1927 1.4355 0.4541 0.08 Uiso 0.318(8) d PR 4 B
C22 C 0.192(2) 1.230(4) 0.5705(17) 0.057(8) Uani 0.682(8) d PD 3 B
H22 H 0.2337 1.1039 0.5656 0.068 Uiso 0.682(8) calc PR 3 B
C23 C 0.4483(3) 1.2496(7) 0.8271(3) 0.0445(10) Uani 1 d . . .
C24 C 0.5556(4) 1.3765(7) 0.8524(3) 0.0461(9) Uani 1 d . . .
H24 H 0.6229 1.3488 0.8348 0.055 Uiso 1 calc R . .
C25 C 0.5375(4) 1.5476(10) 0.9081(4) 0.0652(14) Uani 1 d . . .
H25 H 0.5941 1.6507 0.931 0.078 Uiso 1 calc R . .
C26 C 0.4351(5) 1.5542(10) 0.9262(3) 0.0635(13) Uani 1 d . . .
H26 H 0.4141 1.6593 0.9626 0.076 Uiso 1 calc R . .
S1 S -0.14998(12) 1.1136(3) 0.86564(11) 0.0789(5) Uani 1 d . . .
S2 S 0.17199(8) 0.8420(2) 0.83731(7) 0.0501(3) Uani 1 d . . .
S3 S 0.35078(9) 0.7137(2) 0.67936(8) 0.0514(3) Uani 1 d . . .
S4 S 0.5204(14) 0.442(5) 0.5826(14) 0.083(4) Uani 0.350(9) d P 2 A
S5 S 0.7127(4) 0.6667(7) 0.6813(3) 0.0757(13) Uani 0.650(9) d P 1 A
S6 S 0.0659(5) 1.5143(8) 0.6226(3) 0.0548(9) Uani 0.682(8) d P 3 B
S7 S 0.2117(16) 1.210(3) 0.5636(10) 0.054(3) Uani 0.318(8) d P 4 B
S8 S 0.34771(11) 1.3516(3) 0.87624(9) 0.0636(3) Uani 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
C1 0.045(3) 0.110(5) 0.076(3) 0.010(4) 0.028(2) 0.005(3)
C2 0.044(3) 0.107(5) 0.077(3) 0.030(3) 0.028(2) 0.002(3)
C3 0.0234(17) 0.094(4) 0.059(2) 0.030(3) 0.0209(17) -0.001(2)
C4 0.037(2) 0.070(3) 0.055(3) 0.007(2) 0.0158(19) -0.005(2)
C5 0.0317(19) 0.061(3) 0.057(2) 0.003(2) 0.0132(17) -0.0048(19)
C6 0.0275(17) 0.064(3) 0.056(2) 0.008(2) 0.0147(17) 0.0096(19)
C7 0.0328(19) 0.054(3) 0.049(2) -0.001(2) 0.0134(16) 0.0008(18)
C8 0.0293(19) 0.052(3) 0.051(2) -0.001(2) 0.0108(16) 0.0049(17)
C9 0.0321(19) 0.044(2) 0.050(2) 0.0051(19) 0.0137(16) 0.0031(16)
C10 0.0363(19) 0.043(2) 0.047(2) 0.0050(19) 0.0131(16) 0.0035(16)
C11 0.0304(18) 0.059(3) 0.051(2) 0.001(2) 0.0154(16) 0.0035(18)
C12 0.040(2) 0.053(3) 0.046(2) 0.003(2) 0.0140(17) 0.0089(18)
C13 0.051(2) 0.058(3) 0.055(3) 0.006(2) 0.024(2) 0.017(2)
C14 0.088(17) 0.067(15) 0.17(4) 0.01(2) 0.063(18) 0.030(13)
C15 0.099(5) 0.088(5) 0.086(4) -0.026(4) 0.029(3) 0.039(4)
C16 0.064(4) 0.109(5) 0.096(4) 0.008(4) 0.043(3) 0.034(4)
C17 0.007(8) 0.115(19) 0.14(3) -0.102(19) -0.007(8) 0.005(8)
C18 0.0332(18) 0.054(3) 0.051(2) 0.009(2) 0.0060(17) -0.0036(17)
C19 0.036(13) 0.07(2) 0.078(18) -0.020(13) 0.023(9) 0.009(10)
C20 0.058(3) 0.060(3) 0.078(4) 0.014(3) 0.002(3) -0.003(2)
C21 0.069(3) 0.080(4) 0.054(3) 0.006(3) 0.022(2) -0.014(3)
C22 0.050(11) 0.066(9) 0.064(10) 0.019(8) 0.032(5) 0.003(6)
C23 0.0350(19) 0.044(2) 0.055(2) 0.007(2) 0.0117(17) -0.0005(17)
C24 0.055(2) 0.036(2) 0.052(2) -0.003(2) 0.0230(18) -0.0011(19)
C25 0.053(3) 0.063(3) 0.077(3) -0.004(3) 0.011(2) -0.011(2)
C26 0.075(3) 0.058(3) 0.058(3) -0.012(3) 0.017(2) 0.002(3)
S1 0.0575(7) 0.0924(11) 0.0963(11) 0.0107(10) 0.0373(7) 0.0083(7)
S2 0.0382(5) 0.0573(7) 0.0583(6) 0.0110(6) 0.0187(4) 0.0069(5)
S3 0.0396(5) 0.0552(7) 0.0622(7) -0.0068(6) 0.0178(5) 0.0010(5)
S4 0.072(4) 0.089(10) 0.096(5) -0.020(5) 0.036(4) 0.018(4)
S5 0.042(2) 0.095(2) 0.094(2) -0.0158(19) 0.025(2) 0.0062(15)
S6 0.0452(17) 0.0560(18) 0.0643(16) 0.0081(16) 0.0153(12) 0.0060(13)
S7 0.047(5) 0.068(4) 0.052(3) 0.003(3) 0.021(4) -0.005(4)
S8 0.0575(7) 0.0671(8) 0.0713(7) -0.0095(7) 0.0251(6) 0.0012(7)

#------------------ MOLECULAR GEOMETRY --------------------------------------#

_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
C1 C2 1.305(9) . ?
C1 S1 1.670(6) . ?
C2 C3 1.501(6) . ?
C3 C4 1.479(8) . ?
C4 C5 1.469(6) . ?
C4 S1 1.692(5) . ?
C5 C6 1.355(7) . ?
C5 S2 1.711(4) . ?
C6 C7 1.429(5) . ?
C7 C8 1.375(6) . ?
C7 C18 1.474(6) . ?
C8 C9 1.471(5) . ?
C8 S2 1.727(5) . ?
C9 C10 1.391(6) . ?
C9 S3 1.716(5) . ?
C10 C11 1.431(5) . ?
C10 C23 1.452(6) . ?
C11 C12 1.346(7) . ?
C12 C13 1.473(6) . ?
C12 S3 1.704(4) . ?
C13 C17 1.41(2) . ?
C13 C14 1.43(5) . ?
C13 S4 1.60(2) . ?
C13 S5 1.717(7) . ?
C14 C15 1.473(19) . ?
C15 C16 1.307(10) . ?
C15 S4 1.549(14) . ?
C16 C17 1.487(17) . ?
C16 S5 1.636(9) . ?
C18 C19 1.368(17) . ?
C18 C22 1.38(3) . ?
C18 S7 1.66(2) . ?
C18 S6 1.695(6) . ?
C19 C20 1.468(18) . ?
C20 C21 1.335(8) . ?
C20 S6 1.633(7) . ?
C21 C22 1.489(18) . ?
C21 S7 1.547(15) . ?
C23 C24 1.471(6) . ?
C23 S8 1.699(4) . ?
C24 C25 1.407(7) . ?
C25 C26 1.327(8) . ?
C26 S8 1.681(6) . ?

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
C2 C1 S1 114.9(4) . . ?
C1 C2 C3 116.1(5) . . ?
C4 C3 C2 102.4(5) . . ?
C5 C4 C3 124.6(4) . . ?
C5 C4 S1 120.6(4) . . ?
C3 C4 S1 114.9(3) . . ?
C6 C5 C4 127.5(4) . . ?
C6 C5 S2 110.7(3) . . ?
C4 C5 S2 121.8(4) . . ?
C5 C6 C7 114.4(4) . . ?
C8 C7 C6 111.0(4) . . ?
C8 C7 C18 126.7(4) . . ?
C6 C7 C18 122.2(4) . . ?
C7 C8 C9 128.8(4) . . ?
C7 C8 S2 111.3(3) . . ?
C9 C8 S2 119.8(3) . . ?
C10 C9 C8 128.0(4) . . ?
C10 C9 S3 111.6(3) . . ?
C8 C9 S3 120.4(3) . . ?
C9 C10 C11 110.4(4) . . ?
C9 C10 C23 127.2(4) . . ?
C11 C10 C23 122.4(4) . . ?
C12 C11 C10 113.9(4) . . ?
C11 C12 C13 127.6(4) . . ?
C11 C12 S3 111.9(3) . . ?
C13 C12 S3 120.6(4) . . ?
C17 C13 C14 102.6(13) . . ?
C17 C13 C12 129.0(9) . . ?
C14 C13 C12 128.4(10) . . ?
C17 C13 S4 105.6(9) . . ?
C14 C13 S4 10(3) . . ?
C12 C13 S4 124.5(6) . . ?
C17 C13 S5 11.5(13) . . ?
C14 C13 S5 110.8(10) . . ?
C12 C13 S5 120.3(4) . . ?
S4 C13 S5 115.1(5) . . ?
C13 C14 C15 108(3) . . ?
C16 C15 C14 111.9(19) . . ?
C16 C15 S4 118.9(11) . . ?
C14 C15 S4 12(2) . . ?
C15 C16 C17 103.2(9) . . ?
C15 C16 S5 116.9(5) . . ?
C17 C16 S5 15.3(9) . . ?
C13 C17 C16 112.9(15) . . ?
C19 C18 C22 102.1(13) . . ?
C19 C18 C7 129.3(9) . . ?
C22 C18 C7 127.9(10) . . ?
C19 C18 S7 106.6(10) . . ?
C22 C18 S7 5.3(14) . . ?
C7 C18 S7 123.8(6) . . ?
C19 C18 S6 9.9(11) . . ?
C22 C18 S6 111.8(9) . . ?
C7 C18 S6 119.9(3) . . ?
S7 C18 S6 116.2(5) . . ?
C18 C19 C20 116.6(15) . . ?
C21 C20 C19 101.3(9) . . ?
C21 C20 S6 115.4(5) . . ?
C19 C20 S6 14.3(9) . . ?
C20 C21 C22 110.3(12) . . ?
C20 C21 S7 121.5(9) . . ?
C22 C21 S7 11.5(18) . . ?
C18 C22 C21 109.4(18) . . ?
C10 C23 C24 124.7(4) . . ?
C10 C23 S8 124.2(3) . . ?
C24 C23 S8 111.1(3) . . ?
C25 C24 C23 107.2(4) . . ?
C26 C25 C24 116.5(5) . . ?
C25 C26 S8 112.6(4) . . ?
C1 S1 C4 91.6(3) . . ?
C5 S2 C8 92.5(2) . . ?
C12 S3 C9 92.2(2) . . ?
C15 S4 C13 96.5(12) . . ?
C16 S5 C13 91.9(4) . . ?
C20 S6 C18 93.0(4) . . ?
C21 S7 C18 93.9(10) . . ?
C26 S8 C23 92.6(2) . . ?