# 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 'Zhaohui Wang' _publ_contact_author_email WANGZHAOHUI@ICCAS.AC.CN _publ_section_title ; Synthesis, Packing Arrangement and Transistor Performance Based on Dimmers of Dithienothiophenes ; loop_ _publ_author_name 'Zhaohui Wang' 'Wenping Hu' 'Lin Tan' 'Lei Zhang' # Attachment '4.cif' data_shelxl _database_code_depnum_ccdc_archive 'CCDC 680799' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C18 H8 S6' _chemical_formula_sum 'C18 H8 S6' _chemical_formula_weight 416.60 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' _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M 'P 1 21/n 1' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, y+1/2, -z+1/2' '-x, -y, -z' 'x-1/2, -y-1/2, z-1/2' _cell_length_a 6.1973(12) _cell_length_b 4.7149(7) _cell_length_c 27.494(5) _cell_angle_alpha 90.00 _cell_angle_beta 95.383(11) _cell_angle_gamma 90.00 _cell_volume 799.8(2) _cell_formula_units_Z 2 _cell_measurement_temperature 113(2) _cell_measurement_reflns_used 1502 _cell_measurement_theta_min 3.0 _cell_measurement_theta_max 25.0 _exptl_crystal_description platelet _exptl_crystal_colour yellow _exptl_crystal_size_max 0.14 _exptl_crystal_size_mid 0.12 _exptl_crystal_size_min 0.01 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.730 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 424 _exptl_absorpt_coefficient_mu 0.851 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.8901 _exptl_absorpt_correction_T_max 0.9915 _exptl_absorpt_process_details crystalclear _exptl_special_details ; ? ; _diffrn_ambient_temperature 113(2) _diffrn_radiation_wavelength 0.71070 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'rotating anode' _diffrn_radiation_monochromator confocal _diffrn_measurement_device_type 'Rigaku Saturn' _diffrn_measurement_method \w _diffrn_detector_area_resol_mean 7.31 _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 6967 _diffrn_reflns_av_R_equivalents 0.0458 _diffrn_reflns_av_sigmaI/netI 0.0452 _diffrn_reflns_limit_h_min -8 _diffrn_reflns_limit_h_max 8 _diffrn_reflns_limit_k_min -6 _diffrn_reflns_limit_k_max 6 _diffrn_reflns_limit_l_min -36 _diffrn_reflns_limit_l_max 36 _diffrn_reflns_theta_min 2.98 _diffrn_reflns_theta_max 27.85 _reflns_number_total 1886 _reflns_number_gt 1616 _reflns_threshold_expression >2sigma(I) _computing_data_collection CrystalClear _computing_cell_refinement CrystalClear _computing_data_reduction CrystalClear _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics ? _computing_publication_material 'CrystalStructure 3.7.0' _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^)+(0.0339P)^2^+0.6239P] 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 1886 _refine_ls_number_parameters 110 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0545 _refine_ls_R_factor_gt 0.0419 _refine_ls_wR_factor_ref 0.0898 _refine_ls_wR_factor_gt 0.0837 _refine_ls_goodness_of_fit_ref 1.104 _refine_ls_restrained_S_all 1.104 _refine_ls_shift/su_max 0.001 _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 0.57892(9) 0.61523(14) 0.58281(2) 0.01502(16) Uani 1 1 d . . . S2 S 0.01138(10) 0.21155(14) 0.61639(2) 0.01700(17) Uani 1 1 d . . . S3 S 0.61610(10) 0.07555(14) 0.69281(2) 0.01799(17) Uani 1 1 d . . . C1 C 0.4045(4) 0.9409(6) 0.50392(8) 0.0168(5) Uani 1 1 d . . . H1 H 0.2822 0.9948 0.4825 0.020 Uiso 1 1 calc R . . C2 C 0.3680(4) 0.7398(5) 0.54183(8) 0.0145(5) Uani 1 1 d . . . C3 C 0.1736(4) 0.6216(5) 0.55039(8) 0.0148(5) Uani 1 1 d . . . H3 H 0.0402 0.6650 0.5320 0.018 Uiso 1 1 calc R . . C4 C 0.1935(4) 0.4283(5) 0.58957(8) 0.0152(5) Uani 1 1 d . . . C5 C 0.4039(4) 0.4010(5) 0.61126(8) 0.0144(5) Uani 1 1 d . . . C6 C 0.4179(4) 0.2042(5) 0.65050(9) 0.0153(5) Uani 1 1 d . . . C7 C 0.2186(4) 0.0819(5) 0.65699(8) 0.0144(5) Uani 1 1 d . . . C8 C 0.2286(4) -0.1222(6) 0.69522(8) 0.0177(5) Uani 1 1 d . . . H8 H 0.1082 -0.2295 0.7039 0.021 Uiso 1 1 calc R . . C9 C 0.4318(4) -0.1434(6) 0.71758(9) 0.0189(5) Uani 1 1 d . . . H9 H 0.4695 -0.2670 0.7443 0.023 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 S1 0.0128(3) 0.0159(3) 0.0160(3) 0.0026(2) -0.0004(2) 0.0002(2) S2 0.0129(3) 0.0176(4) 0.0204(3) 0.0042(2) 0.0014(2) 0.0002(2) S3 0.0170(3) 0.0205(4) 0.0159(3) 0.0039(2) -0.0014(2) 0.0018(3) C1 0.0171(11) 0.0174(14) 0.0153(11) -0.0006(10) -0.0021(9) 0.0040(10) C2 0.0141(11) 0.0131(13) 0.0160(11) -0.0012(10) -0.0001(9) 0.0022(10) C3 0.0154(11) 0.0136(13) 0.0151(11) -0.0015(9) -0.0012(9) 0.0028(10) C4 0.0155(12) 0.0128(13) 0.0172(12) -0.0011(10) 0.0016(9) 0.0009(10) C5 0.0146(11) 0.0149(13) 0.0139(11) -0.0003(10) 0.0016(9) 0.0016(10) C6 0.0170(12) 0.0131(13) 0.0154(11) 0.0005(10) 0.0000(9) 0.0013(10) C7 0.0149(11) 0.0118(13) 0.0167(11) -0.0002(9) 0.0027(9) 0.0019(9) C8 0.0205(13) 0.0152(14) 0.0179(12) 0.0021(10) 0.0051(10) 0.0006(10) C9 0.0235(13) 0.0169(14) 0.0164(12) 0.0035(10) 0.0029(10) 0.0021(11) _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 C5 1.723(3) . ? S1 C2 1.746(2) . ? S2 C7 1.732(2) . ? S2 C4 1.737(3) . ? S3 C6 1.721(2) . ? S3 C9 1.726(3) . ? C1 C1 1.344(5) 3_676 ? C1 C2 1.443(3) . ? C1 H1 0.9500 . ? C2 C3 1.368(3) . ? C3 C4 1.407(3) . ? C3 H3 0.9500 . ? C4 C5 1.388(3) . ? C5 C6 1.420(3) . ? C6 C7 1.389(3) . ? C7 C8 1.422(3) . ? C8 C9 1.353(3) . ? C8 H8 0.9500 . ? C9 H9 0.9500 . ? 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 C5 S1 C2 91.43(12) . . ? C7 S2 C4 90.52(12) . . ? C6 S3 C9 91.19(12) . . ? C1 C1 C2 126.1(3) 3_676 . ? C1 C1 H1 117.0 3_676 . ? C2 C1 H1 117.0 . . ? C3 C2 C1 126.4(2) . . ? C3 C2 S1 111.73(18) . . ? C1 C2 S1 121.91(18) . . ? C2 C3 C4 112.3(2) . . ? C2 C3 H3 123.8 . . ? C4 C3 H3 123.8 . . ? C5 C4 C3 113.6(2) . . ? C5 C4 S2 112.63(18) . . ? C3 C4 S2 133.78(19) . . ? C4 C5 C6 112.0(2) . . ? C4 C5 S1 110.90(18) . . ? C6 C5 S1 137.07(19) . . ? C7 C6 C5 112.2(2) . . ? C7 C6 S3 110.71(18) . . ? C5 C6 S3 137.1(2) . . ? C6 C7 C8 113.5(2) . . ? C6 C7 S2 112.65(18) . . ? C8 C7 S2 133.89(19) . . ? C9 C8 C7 111.1(2) . . ? C9 C8 H8 124.4 . . ? C7 C8 H8 124.4 . . ? C8 C9 S3 113.5(2) . . ? C8 C9 H9 123.2 . . ? S3 C9 H9 123.2 . . ? 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 C1 C1 C2 C3 179.1(3) 3_676 . . . ? C1 C1 C2 S1 -1.6(5) 3_676 . . . ? C5 S1 C2 C3 0.4(2) . . . . ? C5 S1 C2 C1 -179.0(2) . . . . ? C1 C2 C3 C4 178.7(2) . . . . ? S1 C2 C3 C4 -0.6(3) . . . . ? C2 C3 C4 C5 0.6(3) . . . . ? C2 C3 C4 S2 -178.5(2) . . . . ? C7 S2 C4 C5 -0.2(2) . . . . ? C7 S2 C4 C3 178.9(3) . . . . ? C3 C4 C5 C6 -179.9(2) . . . . ? S2 C4 C5 C6 -0.6(3) . . . . ? C3 C4 C5 S1 -0.2(3) . . . . ? S2 C4 C5 S1 179.00(13) . . . . ? C2 S1 C5 C4 -0.10(19) . . . . ? C2 S1 C5 C6 179.4(3) . . . . ? C4 C5 C6 C7 1.4(3) . . . . ? S1 C5 C6 C7 -178.1(2) . . . . ? C4 C5 C6 S3 -178.3(2) . . . . ? S1 C5 C6 S3 2.2(5) . . . . ? C9 S3 C6 C7 1.1(2) . . . . ? C9 S3 C6 C5 -179.2(3) . . . . ? C5 C6 C7 C8 178.4(2) . . . . ? S3 C6 C7 C8 -1.9(3) . . . . ? C5 C6 C7 S2 -1.5(3) . . . . ? S3 C6 C7 S2 178.28(12) . . . . ? C4 S2 C7 C6 1.0(2) . . . . ? C4 S2 C7 C8 -178.9(3) . . . . ? C6 C7 C8 C9 1.8(3) . . . . ? S2 C7 C8 C9 -178.3(2) . . . . ? C7 C8 C9 S3 -1.0(3) . . . . ? C6 S3 C9 C8 -0.1(2) . . . . ? _diffrn_measured_fraction_theta_max 0.991 _diffrn_reflns_theta_full 27.85 _diffrn_measured_fraction_theta_full 0.991 _refine_diff_density_max 0.435 _refine_diff_density_min -0.294 _refine_diff_density_rms 0.084