Supplementary Material (ESI) for Journal of Materials Chemistry
This journal is (c) The Royal Society of Chemistry 2004

data_global

_journal_coden_Cambridge         1145

loop_
_publ_author_name
'Peter John, Skabara'

_publ_contact_author_name        'Dr Peter John Skabara'
_publ_contact_author_address     
;
Chemistry
University of Manchester
Oxford Road
Manchester
M13 9PL
UNITED KINGDOM
;

_publ_contact_author_email       PETER.SKABARA@MAN.AC.UK

_publ_requested_journal          'Journal of Materials Chemistry'

_publ_section_title              
;
The electroactivity of tetrathiafulvalene vs
polythiophene: synthesis and characterisation of a fused thieno-TTF
polymer
;

data_s92
_database_code_depnum_ccdc_archive 'CCDC 229182'

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C20 H26 Br2 S7'
_chemical_formula_weight         650.65

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'
S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Br Br -0.2901 2.4595 '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                   7.7910(16)
_cell_length_b                   11.819(2)
_cell_length_c                   15.064(3)
_cell_angle_alpha                96.69(3)
_cell_angle_beta                 98.74(3)
_cell_angle_gamma                104.21(3)
_cell_volume                     1311.9(5)
_cell_formula_units_Z            2
_cell_measurement_temperature    150(2)
_cell_measurement_reflns_used    14353
_cell_measurement_theta_min      2.09
_cell_measurement_theta_max      27.44

_exptl_crystal_description       needle
_exptl_crystal_colour            orange
_exptl_crystal_size_max          0.55
_exptl_crystal_size_mid          0.075
_exptl_crystal_size_min          0.025
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.647
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             656
_exptl_absorpt_coefficient_mu    3.654
_exptl_absorpt_correction_type   multi-scans
_exptl_absorpt_correction_T_min  0.755
_exptl_absorpt_correction_T_max  0.939
_exptl_absorpt_process_details   ?

_exptl_special_details           
;
?
;

_diffrn_ambient_temperature      150(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'Nonius FR591 rotating anode'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Nonius KappaCCD Area Detector'
_diffrn_measurement_method       'Phi and Omega scans to fill Ewald Sphere'
_diffrn_detector_area_resol_mean 9.091
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            14353
_diffrn_reflns_av_R_equivalents  0.0720
_diffrn_reflns_av_sigmaI/netI    0.0737
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_theta_min         2.09
_diffrn_reflns_theta_max         27.44
_reflns_number_total             5919
_reflns_number_gt                4738
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       ?
_computing_cell_refinement       'DENZO, COLLECT'
_computing_data_reduction        'DENZO, COLLECT'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1997)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    'CAMERON (Watkin, Pearce 1995)'
_computing_publication_material  ?

_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^)+(0.1000P)^2^+0.0000P] 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     SHELXL
_refine_ls_extinction_coef       0.0112(12)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_number_reflns         5919
_refine_ls_number_parameters     275
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0595
_refine_ls_R_factor_gt           0.0430
_refine_ls_wR_factor_ref         0.1308
_refine_ls_wR_factor_gt          0.1149
_refine_ls_goodness_of_fit_ref   0.860
_refine_ls_restrained_S_all      0.860
_refine_ls_shift/su_max          0.358
_refine_ls_shift/su_mean         0.019

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
Br1 Br 0.06593(4) 0.86891(3) 0.49339(2) 0.02936(13) Uani 1 1 d . . .
Br2 Br -0.18425(6) 0.43698(3) 0.19855(3) 0.04179(14) Uani 1 1 d . . .
S1 S -0.02018(11) 0.68973(7) 0.31233(6) 0.0273(2) Uani 1 1 d . . .
S2 S -0.18778(11) 0.60520(7) 0.56058(6) 0.02568(19) Uani 1 1 d . . .
S3 S -0.31100(11) 0.39028(7) 0.41446(6) 0.0269(2) Uani 1 1 d . . .
S4 S -0.37561(11) 0.44901(7) 0.69923(6) 0.02660(19) Uani 1 1 d . . .
S5 S -0.49446(11) 0.23894(7) 0.55550(6) 0.02637(19) Uani 1 1 d . . .
S6 S -0.53734(11) 0.31920(8) 0.83879(6) 0.0314(2) Uani 1 1 d . . .
S7 S -0.66708(10) 0.07922(7) 0.67549(7) 0.0302(2) Uani 1 1 d . . .
C1 C -0.0367(4) 0.7195(3) 0.4248(2) 0.0227(6) Uani 1 1 d . . .
C2 C -0.1390(4) 0.5440(3) 0.3054(2) 0.0249(7) Uani 1 1 d . . .
C3 C -0.1884(4) 0.5206(3) 0.3855(2) 0.0232(6) Uani 1 1 d . . .
C4 C -0.1301(4) 0.6223(3) 0.4546(2) 0.0223(6) Uani 1 1 d . . .
C5 C -0.2996(4) 0.4532(3) 0.5283(2) 0.0233(6) Uani 1 1 d . . .
C6 C -0.3753(4) 0.3889(3) 0.5869(2) 0.0229(6) Uani 1 1 d . . .
C7 C -0.4842(4) 0.3141(3) 0.7301(2) 0.0241(7) Uani 1 1 d . . .
C8 C -0.5368(4) 0.2188(3) 0.6648(2) 0.0235(7) Uani 1 1 d . . .
C9 C -0.3146(5) 0.3707(3) 0.9107(3) 0.0334(8) Uani 1 1 d . . .
H9A H -0.2479 0.4411 0.8911 0.040 Uiso 1 1 calc R . .
H9B H -0.3281 0.3929 0.9728 0.040 Uiso 1 1 calc R . .
C10 C -0.2055(4) 0.2804(3) 0.9094(3) 0.0311(7) Uani 1 1 d . . .
H10A H -0.2741 0.2085 0.9263 0.037 Uiso 1 1 calc R . .
H10B H -0.1860 0.2613 0.8480 0.037 Uiso 1 1 calc R . .
C11 C -0.0244(5) 0.3239(3) 0.9736(3) 0.0355(8) Uani 1 1 d . . .
H11A H 0.0444 0.3955 0.9563 0.043 Uiso 1 1 calc R . .
H11B H -0.0442 0.3440 1.0348 0.043 Uiso 1 1 calc R . .
C12 C 0.0854(5) 0.2344(4) 0.9738(3) 0.0388(9) Uani 1 1 d . B .
H12A H 0.0139 0.1613 0.9877 0.047 Uiso 1 1 calc R . .
H12B H 0.1108 0.2177 0.9133 0.047 Uiso 1 1 calc R . .
C13 C 0.2615(5) 0.2747(5) 1.0414(3) 0.0521(11) Uani 1 1 d . . .
H13A H 0.3299 0.3479 1.0263 0.062 Uiso 1 1 calc R A 1
H13B H 0.2327 0.2941 1.1008 0.062 Uiso 1 1 calc R A 1
C14 C 0.382(4) 0.198(3) 1.051(2) 0.051(6) Uani 0.50 1 d P B 1
H14A H 0.3155 0.1219 1.0610 0.076 Uiso 0.50 1 calc PR B 1
H14B H 0.4780 0.2325 1.1023 0.076 Uiso 0.50 1 calc PR B 1
H14C H 0.4309 0.1889 0.9970 0.076 Uiso 0.50 1 calc PR B 1
C14 C 0.354(4) 0.170(3) 1.034(2) 0.054(6) Uani 0.50 1 d P B 2
H14D H 0.4710 0.1934 1.0723 0.082 Uiso 0.50 1 calc PR B 2
H14E H 0.3672 0.1501 0.9717 0.082 Uiso 0.50 1 calc PR B 2
H14F H 0.2810 0.1017 1.0518 0.082 Uiso 0.50 1 calc PR B 2
C15 C -0.5193(5) -0.0153(3) 0.6525(3) 0.0323(8) Uani 1 1 d . . .
H15A H -0.5857 -0.0972 0.6491 0.039 Uiso 1 1 calc R . .
H15B H -0.4869 -0.0060 0.5936 0.039 Uiso 1 1 calc R . .
C16 C -0.3492(4) 0.0109(3) 0.7228(3) 0.0310(7) Uani 1 1 d . . .
H16A H -0.3801 0.0114 0.7828 0.037 Uiso 1 1 calc R . .
H16B H -0.2744 0.0890 0.7207 0.037 Uiso 1 1 calc R . .
C17 C -0.2423(5) -0.0792(3) 0.7080(3) 0.0349(8) Uani 1 1 d . . .
H17A H -0.2129 -0.0806 0.6477 0.042 Uiso 1 1 calc R . .
H17B H -0.3163 -0.1571 0.7111 0.042 Uiso 1 1 calc R . .
C18 C -0.0692(5) -0.0512(3) 0.7783(3) 0.0361(8) Uani 1 1 d . . .
H18A H 0.0056 0.0259 0.7737 0.043 Uiso 1 1 calc R . .
H18B H -0.0992 -0.0467 0.8386 0.043 Uiso 1 1 calc R . .
C19 C 0.0391(5) -0.1414(4) 0.7681(3) 0.0445(10) Uani 1 1 d . . .
H19A H 0.0723 -0.1449 0.7085 0.053 Uiso 1 1 calc R . .
H19B H -0.0353 -0.2189 0.7720 0.053 Uiso 1 1 calc R . .
C20 C 0.2094(5) -0.1104(4) 0.8413(4) 0.0537(12) Uani 1 1 d . . .
H20A H 0.2832 -0.0337 0.8377 0.081 Uiso 1 1 calc R . .
H20B H 0.2754 -0.1682 0.8319 0.081 Uiso 1 1 calc R . .
H20C H 0.1767 -0.1100 0.9002 0.081 Uiso 1 1 calc R . .

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
Br1 0.02968(19) 0.01936(19) 0.0373(2) 0.00295(15) 0.00624(15) 0.00399(13)
Br2 0.0601(3) 0.0365(2) 0.0274(2) -0.00208(17) 0.01310(18) 0.01060(18)
S1 0.0300(4) 0.0258(4) 0.0288(5) 0.0081(3) 0.0117(3) 0.0067(3)
S2 0.0310(4) 0.0209(4) 0.0239(4) 0.0023(3) 0.0084(3) 0.0034(3)
S3 0.0327(4) 0.0205(4) 0.0254(5) 0.0033(3) 0.0080(3) 0.0017(3)
S4 0.0311(4) 0.0230(4) 0.0258(5) 0.0042(3) 0.0084(3) 0.0057(3)
S5 0.0309(4) 0.0211(4) 0.0268(5) 0.0050(3) 0.0085(3) 0.0041(3)
S6 0.0271(4) 0.0437(5) 0.0262(5) 0.0094(4) 0.0097(3) 0.0102(4)
S7 0.0245(4) 0.0269(4) 0.0400(5) 0.0125(4) 0.0084(3) 0.0039(3)
C1 0.0213(14) 0.0204(15) 0.0282(18) 0.0067(13) 0.0057(12) 0.0071(11)
C2 0.0251(15) 0.0219(15) 0.0291(19) 0.0036(14) 0.0100(13) 0.0060(12)
C3 0.0200(14) 0.0218(15) 0.0272(18) 0.0024(13) 0.0048(12) 0.0050(12)
C4 0.0237(14) 0.0200(15) 0.0247(17) 0.0054(13) 0.0063(12) 0.0067(12)
C5 0.0223(14) 0.0222(15) 0.0265(18) 0.0073(13) 0.0045(12) 0.0065(12)
C6 0.0205(14) 0.0223(15) 0.0279(18) 0.0064(13) 0.0060(12) 0.0076(12)
C7 0.0198(14) 0.0290(17) 0.0257(18) 0.0098(14) 0.0058(12) 0.0072(12)
C8 0.0204(14) 0.0246(16) 0.0286(18) 0.0105(14) 0.0080(12) 0.0070(12)
C9 0.0342(17) 0.0394(19) 0.027(2) 0.0063(16) 0.0056(14) 0.0108(15)
C10 0.0293(17) 0.0329(18) 0.0293(19) 0.0004(15) 0.0063(14) 0.0067(14)
C11 0.0323(18) 0.045(2) 0.029(2) 0.0051(17) 0.0063(15) 0.0090(15)
C12 0.0331(18) 0.051(2) 0.034(2) 0.0118(18) 0.0102(16) 0.0107(16)
C13 0.042(2) 0.085(3) 0.034(2) 0.014(2) 0.0035(18) 0.025(2)
C14 0.021(6) 0.060(12) 0.064(13) 0.011(8) -0.012(6) 0.008(7)
C14 0.038(11) 0.082(17) 0.049(11) 0.029(12) 0.009(9) 0.016(9)
C15 0.0350(17) 0.0237(16) 0.038(2) 0.0052(15) 0.0055(15) 0.0090(14)
C16 0.0325(17) 0.0267(17) 0.035(2) 0.0075(15) 0.0078(15) 0.0073(14)
C17 0.0362(18) 0.0276(18) 0.041(2) 0.0049(16) 0.0047(16) 0.0108(14)
C18 0.0348(18) 0.038(2) 0.039(2) 0.0117(17) 0.0105(16) 0.0122(15)
C19 0.038(2) 0.040(2) 0.063(3) 0.021(2) 0.0129(19) 0.0160(17)
C20 0.041(2) 0.060(3) 0.068(3) 0.034(3) 0.008(2) 0.018(2)

_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
Br1 C1 1.859(3) . ?
Br2 C2 1.857(3) . ?
S1 C1 1.720(3) . ?
S1 C2 1.727(3) . ?
S2 C4 1.744(3) . ?
S2 C5 1.767(3) . ?
S3 C3 1.743(3) . ?
S3 C5 1.768(4) . ?
S4 C6 1.758(4) . ?
S4 C7 1.763(3) . ?
S5 C6 1.758(3) . ?
S5 C8 1.759(3) . ?
S6 C7 1.746(3) . ?
S6 C9 1.819(4) . ?
S7 C8 1.752(3) . ?
S7 C15 1.832(3) . ?
C1 C4 1.365(4) . ?
C2 C3 1.359(5) . ?
C3 C4 1.425(5) . ?
C5 C6 1.341(5) . ?
C7 C8 1.340(5) . ?
C9 C10 1.520(5) . ?
C10 C11 1.517(5) . ?
C11 C12 1.515(5) . ?
C12 C13 1.513(5) . ?
C13 C14 1.46(4) . ?
C13 C14 1.59(4) . ?
C15 C16 1.507(5) . ?
C16 C17 1.520(5) . ?
C17 C18 1.522(5) . ?
C18 C19 1.521(5) . ?
C19 C20 1.528(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
C1 S1 C2 91.14(16) . . ?
C4 S2 C5 94.43(16) . . ?
C3 S3 C5 94.47(15) . . ?
C6 S4 C7 95.50(16) . . ?
C6 S5 C8 95.32(16) . . ?
C7 S6 C9 101.62(16) . . ?
C8 S7 C15 102.24(15) . . ?
C4 C1 S1 112.1(2) . . ?
C4 C1 Br1 126.3(3) . . ?
S1 C1 Br1 121.69(17) . . ?
C3 C2 S1 112.1(3) . . ?
C3 C2 Br2 126.6(2) . . ?
S1 C2 Br2 121.33(19) . . ?
C2 C3 C4 112.3(3) . . ?
C2 C3 S3 130.6(3) . . ?
C4 C3 S3 117.1(2) . . ?
C1 C4 C3 112.4(3) . . ?
C1 C4 S2 130.5(3) . . ?
C3 C4 S2 117.1(2) . . ?
C6 C5 S2 121.6(3) . . ?
C6 C5 S3 121.5(3) . . ?
S2 C5 S3 116.89(17) . . ?
C5 C6 S5 122.6(3) . . ?
C5 C6 S4 123.1(3) . . ?
S5 C6 S4 114.24(18) . . ?
C8 C7 S6 125.4(3) . . ?
C8 C7 S4 116.9(3) . . ?
S6 C7 S4 117.2(2) . . ?
C7 C8 S7 125.4(3) . . ?
C7 C8 S5 117.6(2) . . ?
S7 C8 S5 116.7(2) . . ?
C10 C9 S6 114.2(3) . . ?
C11 C10 C9 112.8(3) . . ?
C12 C11 C10 113.5(3) . . ?
C13 C12 C11 113.7(4) . . ?
C14 C13 C12 120.6(10) . . ?
C14 C13 C14 14.1(17) . . ?
C12 C13 C14 106.4(10) . . ?
C16 C15 S7 114.0(3) . . ?
C15 C16 C17 112.3(3) . . ?
C16 C17 C18 112.1(3) . . ?
C19 C18 C17 113.9(3) . . ?
C18 C19 C20 111.8(4) . . ?

_diffrn_measured_fraction_theta_max 0.987
_diffrn_reflns_theta_full        27.44
_diffrn_measured_fraction_theta_full 0.987
_refine_diff_density_max         1.024
_refine_diff_density_min         -0.880
_refine_diff_density_rms         0.122