# Supplementary Material (ESI) for Journal of Materials Chemistry # This journal is (c) The Royal Society of Chemistry 2010 data_global _journal_coden_Cambridge 1145 loop_ _publ_author_name 'Chunyan Chi' 'Hardy S O Chan' 'Jing Luo' 'Baomin Zhao' _publ_contact_author_name 'Chunyan Chi' _publ_contact_author_email CHMCC@NUS.EDU.SG _publ_section_title ; Synthesis, Physical Properties and Self-assembly of Star-shaped Oligothiophenes-Substituted and Fused Triphenylenes ; # Attachment 'TTP-9145.cif' data_9145 _database_code_depnum_ccdc_archive 'CCDC 756943' #TrackingRef 'TTP-9145.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C42 H24 S6' _chemical_formula_weight 720.97 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 C2/c loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y, -z+1/2' 'x+1/2, y+1/2, z' '-x+1/2, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y, z-1/2' '-x+1/2, -y+1/2, -z' 'x+1/2, -y+1/2, z-1/2' _cell_length_a 28.047(3) _cell_length_b 16.0284(13) _cell_length_c 7.4162(6) _cell_angle_alpha 90.00 _cell_angle_beta 101.761(2) _cell_angle_gamma 90.00 _cell_volume 3264.0(5) _cell_formula_units_Z 4 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 2567 _cell_measurement_theta_min 2.54 _cell_measurement_theta_max 26.50 _exptl_crystal_description Block _exptl_crystal_colour Yellow _exptl_crystal_size_max 0.70 _exptl_crystal_size_mid 0.30 _exptl_crystal_size_min 0.02 _exptl_crystal_density_meas 'Not Measured' _exptl_crystal_density_diffrn 1.467 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1488 _exptl_absorpt_coefficient_mu 0.452 _exptl_absorpt_correction_type Multi-scan _exptl_absorpt_correction_T_min 0.7425 _exptl_absorpt_correction_T_max 0.9910 _exptl_absorpt_process_details 'Sadabs, (Sheldrick 2001)' _exptl_special_details ; ? ; _diffrn_ambient_temperature 293(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 'CCD area detector' _diffrn_measurement_method 'phi and omega scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 11356 _diffrn_reflns_av_R_equivalents 0.0384 _diffrn_reflns_av_sigmaI/netI 0.0436 _diffrn_reflns_limit_h_min -29 _diffrn_reflns_limit_h_max 36 _diffrn_reflns_limit_k_min -20 _diffrn_reflns_limit_k_max 17 _diffrn_reflns_limit_l_min -9 _diffrn_reflns_limit_l_max 9 _diffrn_reflns_theta_min 1.47 _diffrn_reflns_theta_max 27.50 _reflns_number_total 3755 _reflns_number_gt 3047 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SMART' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _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^)+(0.0850P)^2^+3.6455P] 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 3755 _refine_ls_number_parameters 217 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0763 _refine_ls_R_factor_gt 0.0624 _refine_ls_wR_factor_ref 0.1617 _refine_ls_wR_factor_gt 0.1536 _refine_ls_goodness_of_fit_ref 1.067 _refine_ls_restrained_S_all 1.067 _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 0.18343(3) 0.74470(5) 0.42667(12) 0.0443(2) Uani 1 1 d . . . S2 S 0.18738(3) 0.66080(5) -0.00987(13) 0.0463(2) Uani 1 1 d . . . S3 S 0.01413(3) 0.12855(5) 0.02810(13) 0.0476(3) Uani 1 1 d . . . C1 C 0.10023(9) 0.66395(16) 0.2332(4) 0.0277(5) Uani 1 1 d . . . C2 C 0.12165(9) 0.58888(15) 0.1835(4) 0.0270(5) Uani 1 1 d . . . C3 C 0.09602(9) 0.51523(16) 0.1791(4) 0.0281(5) Uani 1 1 d . . . H3 H 0.1107 0.4661 0.1518 0.034 Uiso 1 1 calc R . . C4 C 0.04864(9) 0.51127(15) 0.2141(3) 0.0251(5) Uani 1 1 d . . . C5 C 0.02528(9) 0.58739(15) 0.2394(3) 0.0258(5) Uani 1 1 d . . . C6 C 0.05249(9) 0.66184(16) 0.2533(4) 0.0283(5) Uani 1 1 d . . . H6 H 0.0377 0.7114 0.2769 0.034 Uiso 1 1 calc R . . C7 C 0.02333(9) 0.43258(15) 0.2277(3) 0.0250(5) Uani 1 1 d . . . C8 C 0.04452(9) 0.35559(15) 0.2004(3) 0.0269(5) Uani 1 1 d . . . H8 H 0.0748 0.3554 0.1675 0.032 Uiso 1 1 calc R . . C9 C 0.02240(9) 0.27977(16) 0.2202(3) 0.0271(5) Uani 1 1 d . . . C10 C 0.12855(9) 0.74251(16) 0.2702(4) 0.0294(6) Uani 1 1 d . . . C11 C 0.11785(11) 0.81806(19) 0.1956(5) 0.0430(7) Uani 1 1 d . . . H11 H 0.0894 0.8299 0.1104 0.052 Uiso 1 1 calc R . . C12 C 0.15463(13) 0.8783(2) 0.2607(6) 0.0558(9) Uani 1 1 d . . . H12 H 0.1529 0.9335 0.2209 0.067 Uiso 1 1 calc R . . C13 C 0.19186(12) 0.8476(2) 0.3848(5) 0.0487(8) Uani 1 1 d . . . H13 H 0.2189 0.8784 0.4411 0.058 Uiso 1 1 calc R . . C14 C 0.17125(10) 0.58900(15) 0.1408(4) 0.0298(6) Uani 1 1 d . . . C15 C 0.20926(11) 0.53892(19) 0.2108(4) 0.0407(7) Uani 1 1 d . . . H15 H 0.2076 0.4951 0.2914 0.049 Uiso 1 1 calc R . . C16 C 0.25205(11) 0.5607(2) 0.1474(5) 0.0512(8) Uani 1 1 d . . . H16 H 0.2816 0.5332 0.1846 0.061 Uiso 1 1 calc R . . C17 C 0.24578(12) 0.6248(2) 0.0286(5) 0.0499(9) Uani 1 1 d . . . H17 H 0.2701 0.6468 -0.0258 0.060 Uiso 1 1 calc R . . C18 C 0.04608(9) 0.20236(15) 0.1718(4) 0.0278(5) Uani 1 1 d . . . C19 C 0.09373(11) 0.18064(19) 0.2175(5) 0.0435(7) Uani 1 1 d . . . H19 H 0.1173 0.2133 0.2914 0.052 Uiso 1 1 calc R . . C20 C 0.10383(13) 0.1037(2) 0.1418(6) 0.0575(10) Uani 1 1 d . . . H20 H 0.1348 0.0802 0.1619 0.069 Uiso 1 1 calc R . . C21 C 0.06447(13) 0.06773(19) 0.0379(5) 0.0508(8) Uani 1 1 d . . . H21 H 0.0646 0.0165 -0.0209 0.061 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 0.0351(4) 0.0379(4) 0.0541(5) -0.0020(3) -0.0050(3) -0.0031(3) S2 0.0470(5) 0.0334(4) 0.0660(6) 0.0115(3) 0.0291(4) 0.0043(3) S3 0.0383(4) 0.0378(4) 0.0644(6) -0.0204(4) 0.0052(4) -0.0019(3) C1 0.0274(12) 0.0254(12) 0.0299(13) 0.0016(10) 0.0045(10) -0.0001(10) C2 0.0247(12) 0.0256(12) 0.0306(13) 0.0026(10) 0.0051(10) 0.0007(10) C3 0.0262(12) 0.0244(12) 0.0339(14) 0.0008(10) 0.0063(10) 0.0026(10) C4 0.0261(12) 0.0250(12) 0.0238(12) 0.0015(9) 0.0042(9) 0.0003(10) C5 0.0277(13) 0.0252(12) 0.0242(12) 0.0011(9) 0.0042(10) 0.0009(10) C6 0.0285(13) 0.0238(12) 0.0318(13) -0.0004(10) 0.0046(10) 0.0023(10) C7 0.0278(12) 0.0231(12) 0.0235(12) 0.0007(9) 0.0040(9) -0.0012(10) C8 0.0241(12) 0.0273(13) 0.0296(13) -0.0005(10) 0.0061(10) 0.0004(10) C9 0.0276(12) 0.0234(12) 0.0290(13) -0.0014(10) 0.0028(10) 0.0007(10) C10 0.0231(12) 0.0294(13) 0.0358(14) -0.0031(10) 0.0061(10) -0.0015(10) C11 0.0317(14) 0.0341(15) 0.060(2) 0.0015(14) 0.0025(13) -0.0029(12) C12 0.0485(19) 0.0278(15) 0.088(3) 0.0021(16) 0.0072(18) -0.0072(14) C13 0.0351(16) 0.0371(16) 0.073(2) -0.0137(15) 0.0089(15) -0.0094(13) C14 0.0315(13) 0.0233(12) 0.0356(14) -0.0010(10) 0.0092(11) -0.0046(10) C15 0.0368(15) 0.0366(16) 0.0486(17) 0.0035(13) 0.0080(13) 0.0007(12) C16 0.0276(15) 0.0478(18) 0.076(2) -0.0107(17) 0.0052(15) 0.0073(13) C17 0.0386(16) 0.0415(17) 0.077(2) -0.0180(16) 0.0288(16) -0.0113(13) C18 0.0295(13) 0.0212(12) 0.0326(14) 0.0014(10) 0.0059(10) -0.0009(10) C19 0.0346(15) 0.0323(15) 0.062(2) -0.0048(14) 0.0054(14) 0.0027(12) C20 0.0409(18) 0.0384(18) 0.094(3) -0.0028(18) 0.0155(18) 0.0119(14) C21 0.055(2) 0.0259(14) 0.077(2) -0.0096(14) 0.0263(18) 0.0047(13) _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 C13 1.703(3) . ? S1 C10 1.729(3) . ? S2 C17 1.705(3) . ? S2 C14 1.727(3) . ? S3 C21 1.705(3) . ? S3 C18 1.717(3) . ? C1 C6 1.378(4) . ? C1 C2 1.426(4) . ? C1 C10 1.484(3) . ? C2 C3 1.379(4) . ? C2 C14 1.489(4) . ? C3 C4 1.406(3) . ? C4 C5 1.415(3) . ? C4 C7 1.461(3) . ? C5 C6 1.409(3) . ? C5 C5 1.458(5) 2 ? C7 C8 1.402(3) . ? C7 C7 1.414(5) 2 ? C8 C9 1.386(3) . ? C9 C9 1.414(5) 2 ? C9 C18 1.486(3) . ? C10 C11 1.340(4) . ? C11 C12 1.424(4) . ? C12 C13 1.338(5) . ? C14 C15 1.351(4) . ? C15 C16 1.419(5) . ? C16 C17 1.341(5) . ? C18 C19 1.355(4) . ? C19 C20 1.407(5) . ? C20 C21 1.341(5) . ? 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 C13 S1 C10 92.01(15) . . ? C17 S2 C14 92.06(16) . . ? C21 S3 C18 92.55(15) . . ? C6 C1 C2 118.5(2) . . ? C6 C1 C10 119.7(2) . . ? C2 C1 C10 121.7(2) . . ? C3 C2 C1 118.9(2) . . ? C3 C2 C14 120.1(2) . . ? C1 C2 C14 121.0(2) . . ? C2 C3 C4 122.8(2) . . ? C3 C4 C5 117.8(2) . . ? C3 C4 C7 122.9(2) . . ? C5 C4 C7 119.4(2) . . ? C6 C5 C4 118.8(2) . . ? C6 C5 C5 121.10(15) . 2 ? C4 C5 C5 120.06(14) . 2 ? C1 C6 C5 122.5(2) . . ? C8 C7 C7 118.27(14) . 2 ? C8 C7 C4 121.6(2) . . ? C7 C7 C4 120.15(14) 2 . ? C9 C8 C7 123.0(2) . . ? C8 C9 C9 118.60(15) . 2 ? C8 C9 C18 118.3(2) . . ? C9 C9 C18 123.02(14) 2 . ? C11 C10 C1 128.6(2) . . ? C11 C10 S1 110.6(2) . . ? C1 C10 S1 120.73(19) . . ? C10 C11 C12 112.8(3) . . ? C13 C12 C11 113.2(3) . . ? C12 C13 S1 111.4(2) . . ? C15 C14 C2 128.0(2) . . ? C15 C14 S2 110.7(2) . . ? C2 C14 S2 121.20(19) . . ? C14 C15 C16 112.4(3) . . ? C17 C16 C15 113.6(3) . . ? C16 C17 S2 111.2(2) . . ? C19 C18 C9 128.4(2) . . ? C19 C18 S3 110.0(2) . . ? C9 C18 S3 121.52(19) . . ? C18 C19 C20 113.2(3) . . ? C21 C20 C19 113.4(3) . . ? C20 C21 S3 110.9(2) . . ? _diffrn_measured_fraction_theta_max 1.000 _diffrn_reflns_theta_full 27.50 _diffrn_measured_fraction_theta_full 1.000 _refine_diff_density_max 0.512 _refine_diff_density_min -0.254 _refine_diff_density_rms 0.090