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