# Supplementary Material (ESI) for Journal of Materials Chemistry # This journal is © The Royal Society of Chemistry 2005 data_global _journal_coden_Cambridge 1145 loop_ _publ_author_name 'Peter Skabara' 'Simon J. Coles' 'Mark Giles' 'Michael B. Hursthouse' 'Iain McCulloch' 'Howard J. Spencer' _publ_contact_author_name 'Peter Skabara' _publ_contact_author_address ; Department of Chemistry The University of Manchester Oxford Road Manchester M13 9PL UNITED KINGDOM ; _publ_contact_author_email PETER.SKABARA@MANCHESTER.AC.UK _publ_requested_journal 'Journal of Materials Chemistry' _publ_section_title ; The first direct experimental comparison between the hugely contrasting properties of PEDOT and the all-sulfur analogue PEDTT by analogy with well-defined EDTT-EDOT copolymers ; data_OSO _database_code_depnum_ccdc_archive 'CCDC 280116' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C18 H14 O4 S5' _chemical_formula_weight 454.59 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' O O 0.0106 0.0060 '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 P2(1) loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z' _cell_length_a 9.9758(7) _cell_length_b 7.6623(3) _cell_length_c 12.8922(9) _cell_angle_alpha 90.00 _cell_angle_beta 112.418(5) _cell_angle_gamma 90.00 _cell_volume 910.97(10) _cell_formula_units_Z 2 _cell_measurement_temperature 120(2) _cell_measurement_reflns_used 4806 _cell_measurement_theta_min 2.91 _cell_measurement_theta_max 27.48 _exptl_crystal_description block _exptl_crystal_colour yellow _exptl_crystal_size_max 0.40 _exptl_crystal_size_mid 0.40 _exptl_crystal_size_min 0.20 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.657 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 468 _exptl_absorpt_coefficient_mu 0.660 _exptl_absorpt_correction_type multi-scans _exptl_absorpt_correction_T_min 0.7782 _exptl_absorpt_correction_T_max 0.8793 _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 120(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'Bruker-Nonius FR591 rotating anode' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Bruker-Nonius KappaCCD Area Detector' _diffrn_measurement_method '\f and \w scans to fill Ewald Sphere' _diffrn_detector_area_resol_mean 9.091 _diffrn_standards_decay_% negligible _diffrn_reflns_number 7732 _diffrn_reflns_av_R_equivalents 0.0371 _diffrn_reflns_av_sigmaI/netI 0.0469 _diffrn_reflns_limit_h_min -12 _diffrn_reflns_limit_h_max 12 _diffrn_reflns_limit_k_min -9 _diffrn_reflns_limit_k_max 9 _diffrn_reflns_limit_l_min -16 _diffrn_reflns_limit_l_max 13 _diffrn_reflns_theta_min 3.16 _diffrn_reflns_theta_max 27.50 _reflns_number_total 4040 _reflns_number_gt 3872 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'DENZO (Otwinowski & Minor, 1997) & COLLECT (Hooft, 1998)' _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 'PLATON (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^)+(0.0214P)^2^+0.2735P] 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 SHELXL _refine_ls_extinction_coef 0.0044(15) _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _refine_ls_abs_structure_Flack 0.04(5) _refine_ls_number_reflns 4040 _refine_ls_number_parameters 245 _refine_ls_number_restraints 1 _refine_ls_R_factor_all 0.0294 _refine_ls_R_factor_gt 0.0265 _refine_ls_wR_factor_ref 0.0615 _refine_ls_wR_factor_gt 0.0600 _refine_ls_goodness_of_fit_ref 1.033 _refine_ls_restrained_S_all 1.033 _refine_ls_shift/su_max 0.006 _refine_ls_shift/su_mean 0.001 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 C1 C 0.2085(2) 0.6326(3) 0.24550(16) 0.0167(4) Uani 1 1 d . . . C2 C 0.1018(2) 0.7399(3) 0.17668(16) 0.0155(4) Uani 1 1 d . . . C3 C -0.0411(2) 0.6767(3) 0.15508(16) 0.0165(4) Uani 1 1 d . . . C4 C -0.0406(2) 0.5202(3) 0.20823(16) 0.0162(4) Uani 1 1 d . . . C5 C -0.0144(2) 1.0605(3) 0.10829(19) 0.0248(5) Uani 1 1 d . . . H5A H -0.0196 1.0712 0.1832 0.030 Uiso 1 1 calc R . . H5B H -0.0044 1.1793 0.0820 0.030 Uiso 1 1 calc R . . C6 C -0.1526(2) 0.9800(3) 0.0283(2) 0.0280(5) Uani 1 1 d . . . H6A H -0.1415 0.9562 -0.0435 0.034 Uiso 1 1 calc R . . H6B H -0.2318 1.0661 0.0129 0.034 Uiso 1 1 calc R . . C7 C -0.16076(19) 0.4123(3) 0.20660(16) 0.0167(4) Uani 1 1 d . . . C8 C -0.1610(2) 0.2959(3) 0.28757(17) 0.0179(4) Uani 1 1 d . . . C9 C -0.2927(2) 0.2022(3) 0.25911(18) 0.0218(4) Uani 1 1 d . . . C10 C -0.3922(2) 0.2456(3) 0.15715(19) 0.0256(5) Uani 1 1 d . . . H10 H -0.4864 0.1961 0.1248 0.031 Uiso 1 1 calc R . . C11 C -0.0788(2) 0.1693(3) 0.46642(18) 0.0241(5) Uani 1 1 d . . . H11A H -0.1265 0.2463 0.5037 0.029 Uiso 1 1 calc R . . H11B H 0.0113 0.1233 0.5245 0.029 Uiso 1 1 calc R . . C12 C -0.1777(2) 0.0207(3) 0.41104(19) 0.0260(5) Uani 1 1 d . . . H12A H -0.1303 -0.0557 0.3732 0.031 Uiso 1 1 calc R . . H12B H -0.1961 -0.0496 0.4687 0.031 Uiso 1 1 calc R . . C13 C 0.3657(2) 0.6459(3) 0.28317(17) 0.0167(4) Uani 1 1 d . . . C14 C 0.4692(2) 0.6037(3) 0.38566(17) 0.0170(4) Uani 1 1 d . . . C15 C 0.6127(2) 0.6222(3) 0.38964(17) 0.0179(4) Uani 1 1 d . . . C16 C 0.6179(2) 0.6779(3) 0.29216(17) 0.0202(4) Uani 1 1 d . . . H16 H 0.7050 0.6977 0.2803 0.024 Uiso 1 1 calc R . . C17 C 0.5635(2) 0.5713(3) 0.57950(17) 0.0228(5) Uani 1 1 d . . . H17A H 0.5464 0.5111 0.6413 0.027 Uiso 1 1 calc R . . H17B H 0.5786 0.6969 0.5984 0.027 Uiso 1 1 calc R . . C18 C 0.6965(2) 0.4968(3) 0.56730(18) 0.0250(5) Uani 1 1 d . . . H18A H 0.7791 0.5020 0.6406 0.030 Uiso 1 1 calc R . . H18B H 0.6790 0.3727 0.5448 0.030 Uiso 1 1 calc R . . O1 O -0.04321(14) 0.2691(2) 0.38506(12) 0.0213(3) Uani 1 1 d . . . O2 O -0.31408(15) 0.0829(2) 0.32976(14) 0.0282(4) Uani 1 1 d . . . O3 O 0.43797(14) 0.5494(2) 0.47556(12) 0.0196(3) Uani 1 1 d . . . O4 O 0.73309(15) 0.5909(2) 0.48494(12) 0.0236(3) Uani 1 1 d . . . S1 S 0.13518(5) 0.45196(6) 0.28426(4) 0.01715(11) Uani 1 1 d . . . S2 S 0.14278(5) 0.93327(6) 0.12031(4) 0.02026(12) Uani 1 1 d . . . S3 S -0.20557(6) 0.78066(7) 0.07628(5) 0.02854(14) Uani 1 1 d . . . S4 S -0.32621(5) 0.40165(7) 0.09385(4) 0.02189(12) Uani 1 1 d . . . S5 S 0.44812(5) 0.70830(7) 0.19260(4) 0.02178(13) Uani 1 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 0.0188(9) 0.0163(10) 0.0131(9) -0.0001(8) 0.0039(7) 0.0013(8) C2 0.0190(9) 0.0163(10) 0.0115(9) -0.0008(7) 0.0061(7) -0.0007(8) C3 0.0175(9) 0.0180(9) 0.0135(9) 0.0002(8) 0.0054(7) 0.0034(8) C4 0.0143(9) 0.0176(9) 0.0156(10) 0.0016(8) 0.0044(7) 0.0029(8) C5 0.0304(11) 0.0153(10) 0.0272(12) 0.0035(9) 0.0092(9) 0.0037(9) C6 0.0267(11) 0.0230(12) 0.0306(12) 0.0125(10) 0.0067(9) 0.0065(9) C7 0.0146(8) 0.0182(10) 0.0172(9) -0.0014(8) 0.0058(7) 0.0004(8) C8 0.0153(9) 0.0196(10) 0.0191(10) -0.0001(8) 0.0069(8) 0.0014(8) C9 0.0178(9) 0.0225(10) 0.0258(11) 0.0012(9) 0.0089(8) -0.0007(9) C10 0.0182(9) 0.0308(12) 0.0261(12) 0.0013(10) 0.0065(8) -0.0043(9) C11 0.0235(10) 0.0279(11) 0.0205(11) 0.0066(9) 0.0081(9) -0.0010(9) C12 0.0224(10) 0.0277(11) 0.0272(12) 0.0079(10) 0.0085(9) -0.0031(9) C13 0.0169(9) 0.0158(9) 0.0181(10) -0.0002(8) 0.0075(8) -0.0013(8) C14 0.0174(9) 0.0166(9) 0.0170(10) 0.0005(8) 0.0066(8) -0.0009(8) C15 0.0160(9) 0.0184(10) 0.0169(10) -0.0002(8) 0.0035(8) -0.0016(8) C16 0.0172(9) 0.0240(11) 0.0193(10) -0.0017(9) 0.0067(8) -0.0036(8) C17 0.0190(9) 0.0301(12) 0.0170(10) 0.0049(9) 0.0043(8) 0.0013(9) C18 0.0203(10) 0.0327(12) 0.0201(10) 0.0119(9) 0.0057(8) 0.0052(9) O1 0.0160(6) 0.0249(7) 0.0195(7) 0.0087(6) 0.0028(6) -0.0022(6) O2 0.0203(7) 0.0316(8) 0.0312(9) 0.0110(7) 0.0082(7) -0.0029(7) O3 0.0132(6) 0.0292(8) 0.0142(7) 0.0065(6) 0.0028(5) 0.0001(6) O4 0.0168(6) 0.0319(8) 0.0206(8) 0.0048(7) 0.0056(6) -0.0024(7) S1 0.0139(2) 0.0159(2) 0.0187(2) 0.00371(19) 0.00297(17) -0.00003(19) S2 0.0244(2) 0.0170(2) 0.0205(2) 0.0039(2) 0.00991(19) 0.0005(2) S3 0.0178(2) 0.0262(3) 0.0365(3) 0.0149(2) 0.0047(2) 0.0049(2) S4 0.0168(2) 0.0269(3) 0.0180(2) 0.0011(2) 0.00234(18) -0.0019(2) S5 0.0194(2) 0.0311(3) 0.0150(2) 0.0018(2) 0.00674(19) -0.0031(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 C1 C2 1.370(3) . ? C1 C13 1.457(3) . ? C1 S1 1.726(2) . ? C2 C3 1.428(3) . ? C2 S2 1.766(2) . ? C3 C4 1.380(3) . ? C3 S3 1.757(2) . ? C4 C7 1.450(3) . ? C4 S1 1.7314(19) . ? C5 C6 1.503(3) . ? C5 S2 1.802(2) . ? C6 S3 1.801(2) . ? C7 C8 1.374(3) . ? C7 S4 1.7360(19) . ? C8 O1 1.370(2) . ? C8 C9 1.417(3) . ? C9 C10 1.352(3) . ? C9 O2 1.364(3) . ? C10 S4 1.714(2) . ? C11 O1 1.448(2) . ? C11 C12 1.498(3) . ? C12 O2 1.445(2) . ? C13 C14 1.370(3) . ? C13 S5 1.732(2) . ? C14 O3 1.374(2) . ? C14 C15 1.419(3) . ? C15 C16 1.347(3) . ? C15 O4 1.373(2) . ? C16 S5 1.707(2) . ? C17 O3 1.453(2) . ? C17 C18 1.507(3) . ? C18 O4 1.441(3) . ? 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 C13 130.23(18) . . ? C2 C1 S1 110.98(14) . . ? C13 C1 S1 118.72(15) . . ? C1 C2 C3 113.23(17) . . ? C1 C2 S2 121.68(15) . . ? C3 C2 S2 125.08(15) . . ? C4 C3 C2 112.53(17) . . ? C4 C3 S3 120.44(15) . . ? C2 C3 S3 126.98(16) . . ? C3 C4 C7 129.94(17) . . ? C3 C4 S1 110.78(15) . . ? C7 C4 S1 119.28(15) . . ? C6 C5 S2 112.15(16) . . ? C5 C6 S3 115.11(16) . . ? C8 C7 C4 126.90(17) . . ? C8 C7 S4 109.22(14) . . ? C4 C7 S4 123.76(15) . . ? O1 C8 C7 123.02(17) . . ? O1 C8 C9 123.24(18) . . ? C7 C8 C9 113.71(18) . . ? C10 C9 O2 124.75(19) . . ? C10 C9 C8 113.1(2) . . ? O2 C9 C8 122.18(19) . . ? C9 C10 S4 111.17(16) . . ? O1 C11 C12 110.83(18) . . ? O2 C12 C11 111.18(18) . . ? C14 C13 C1 128.65(18) . . ? C14 C13 S5 109.77(14) . . ? C1 C13 S5 121.44(15) . . ? C13 C14 O3 123.70(17) . . ? C13 C14 C15 112.96(18) . . ? O3 C14 C15 123.34(17) . . ? C16 C15 O4 123.93(18) . . ? C16 C15 C14 113.29(18) . . ? O4 C15 C14 122.75(18) . . ? C15 C16 S5 111.37(16) . . ? O3 C17 C18 110.08(18) . . ? O4 C18 C17 111.60(17) . . ? C8 O1 C11 112.47(15) . . ? C9 O2 C12 111.21(15) . . ? C14 O3 C17 110.49(14) . . ? C15 O4 C18 111.45(15) . . ? C1 S1 C4 92.48(10) . . ? C2 S2 C5 99.13(10) . . ? C3 S3 C6 104.55(10) . . ? C10 S4 C7 92.82(10) . . ? C16 S5 C13 92.61(10) . . ? _diffrn_measured_fraction_theta_max 0.995 _diffrn_reflns_theta_full 27.50 _diffrn_measured_fraction_theta_full 0.995 _refine_diff_density_max 0.284 _refine_diff_density_min -0.259 _refine_diff_density_rms 0.051 data_SOS _database_code_depnum_ccdc_archive 'CCDC 280117' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C18 H14 O2 S7' _chemical_formula_weight 486.71 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' O O 0.0106 0.0060 '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 Orthorhombic _symmetry_space_group_name_H-M P2(1)2(1)2(1) loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, -y, z+1/2' '-x, y+1/2, -z+1/2' 'x+1/2, -y+1/2, -z' _cell_length_a 8.1677(13) _cell_length_b 8.4673(15) _cell_length_c 27.674(5) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 1913.9(6) _cell_formula_units_Z 4 _cell_measurement_temperature 120(2) _cell_measurement_reflns_used 4683 _cell_measurement_theta_min 2.91 _cell_measurement_theta_max 27.48 _exptl_crystal_description plate _exptl_crystal_colour 'pale green' _exptl_crystal_size_max 0.05 _exptl_crystal_size_mid 0.04 _exptl_crystal_size_min 0.01 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.689 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1000 _exptl_absorpt_coefficient_mu 0.837 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.9593 _exptl_absorpt_correction_T_max 0.9917 _exptl_absorpt_process_details 'SADABS V2.10 (Sheldrick, G.M., 2003)' _exptl_special_details ; ? ; _diffrn_ambient_temperature 120(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'Bruker-Nonius FR591 rotating anode' _diffrn_radiation_monochromator '10cm confocal mirrors' _diffrn_measurement_device_type 'Bruker-Nonius KappaCCD Area Detector' _diffrn_measurement_method '\f and \w scans' _diffrn_detector_area_resol_mean 9.091 _diffrn_standards_number none _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% negligible _diffrn_reflns_number 40953 _diffrn_reflns_av_R_equivalents 0.1394 _diffrn_reflns_av_sigmaI/netI 0.0817 _diffrn_reflns_limit_h_min -10 _diffrn_reflns_limit_h_max 10 _diffrn_reflns_limit_k_min -10 _diffrn_reflns_limit_k_max 10 _diffrn_reflns_limit_l_min -35 _diffrn_reflns_limit_l_max 35 _diffrn_reflns_theta_min 2.90 _diffrn_reflns_theta_max 27.50 _reflns_number_total 4382 _reflns_number_gt 3389 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'DENZO (Otwinowski & Minor, 1997) & COLLECT (Hooft, 1998)' _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 'PLATON (Spek, 1990)' _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^)+(0.0626P)^2^+1.5975P] 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_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _refine_ls_abs_structure_Flack -0.07(16) _refine_ls_number_reflns 4382 _refine_ls_number_parameters 245 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0986 _refine_ls_R_factor_gt 0.0710 _refine_ls_wR_factor_ref 0.1501 _refine_ls_wR_factor_gt 0.1402 _refine_ls_goodness_of_fit_ref 1.124 _refine_ls_restrained_S_all 1.124 _refine_ls_shift/su_max 0.072 _refine_ls_shift/su_mean 0.017 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 C1 C 0.7307(7) 0.3923(8) 0.1936(2) 0.0346(14) Uani 1 1 d . . . H1A H 0.8300 0.4455 0.2061 0.042 Uiso 1 1 calc R . . H1B H 0.7468 0.2769 0.1970 0.042 Uiso 1 1 calc R . . C2 C 0.7097(8) 0.4323(8) 0.1409(2) 0.0411(16) Uani 1 1 d . . . H2A H 0.8164 0.4202 0.1243 0.049 Uiso 1 1 calc R . . H2B H 0.6762 0.5443 0.1380 0.049 Uiso 1 1 calc R . . C3 C 0.4049(7) 0.2801(7) 0.1545(2) 0.0274(13) Uani 1 1 d . . . C4 C 0.4043(7) 0.3341(6) 0.2036(2) 0.0263(13) Uani 1 1 d . . . C5 C 0.2705(7) 0.1976(8) 0.1437(2) 0.0355(15) Uani 1 1 d . . . H5 H 0.2521 0.1516 0.1129 0.043 Uiso 1 1 calc R . . C6 C 0.2629(7) 0.2883(7) 0.22807(19) 0.0246(12) Uani 1 1 d . . . C7 C 0.2184(7) 0.3161(7) 0.2777(2) 0.0274(13) Uani 1 1 d . . . C8 C 0.0747(7) 0.2743(6) 0.29942(19) 0.0233(12) Uani 1 1 d . . . C9 C 0.0658(7) 0.3083(7) 0.34926(19) 0.0284(12) Uani 1 1 d . . . C10 C 0.1985(7) 0.3837(7) 0.3665(2) 0.0286(13) Uani 1 1 d . . . C11 C -0.1957(7) 0.1975(8) 0.3024(2) 0.0352(14) Uani 1 1 d . . . H11A H -0.2755 0.1241 0.2875 0.042 Uiso 1 1 calc R . . H11B H -0.2435 0.3049 0.3018 0.042 Uiso 1 1 calc R . . C12 C -0.1643(8) 0.1488(8) 0.3540(2) 0.0403(16) Uani 1 1 d . . . H12A H -0.2696 0.1357 0.3713 0.048 Uiso 1 1 calc R . . H12B H -0.1054 0.0467 0.3547 0.048 Uiso 1 1 calc R . . C13 C 0.2252(7) 0.4448(7) 0.4156(2) 0.0311(14) Uani 1 1 d . . . C14 C 0.3629(7) 0.4419(7) 0.44340(19) 0.0293(13) Uani 1 1 d . . . C15 C 0.3383(8) 0.5233(7) 0.48829(19) 0.0330(14) Uani 1 1 d . . . C16 C 0.1883(8) 0.5858(9) 0.4925(2) 0.0465(18) Uani 1 1 d . . . H16 H 0.1516 0.6434 0.5199 0.056 Uiso 1 1 calc R . . C17 C 0.6568(9) 0.3290(8) 0.4782(2) 0.0458(17) Uani 1 1 d . . . H17A H 0.6035 0.2448 0.4973 0.055 Uiso 1 1 calc R . . H17B H 0.7684 0.2921 0.4699 0.055 Uiso 1 1 calc R . . C18 C 0.6711(9) 0.4736(11) 0.5090(3) 0.062(2) Uani 1 1 d . . . H18A H 0.7130 0.5616 0.4889 0.075 Uiso 1 1 calc R . . H18B H 0.7520 0.4535 0.5349 0.075 Uiso 1 1 calc R . . O1 O -0.0495(5) 0.1961(5) 0.27548(13) 0.0348(10) Uani 1 1 d . . . O2 O -0.0678(5) 0.2686(5) 0.37724(13) 0.0352(10) Uani 1 1 d . . . S1 S 0.55691(17) 0.45148(18) 0.22918(5) 0.0298(3) Uani 1 1 d . . . S2 S 0.5588(2) 0.3090(2) 0.11080(5) 0.0388(4) Uani 1 1 d . . . S3 S 0.13445(18) 0.18192(19) 0.19051(5) 0.0331(4) Uani 1 1 d . . . S4 S 0.34137(17) 0.41157(18) 0.32039(5) 0.0280(3) Uani 1 1 d . . . S5 S 0.0710(2) 0.5492(2) 0.44261(6) 0.0485(5) Uani 1 1 d . . . S6 S 0.4794(2) 0.5332(2) 0.53629(5) 0.0428(5) Uani 1 1 d . . . S7 S 0.5452(2) 0.3549(2) 0.42379(6) 0.0456(5) Uani 1 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 0.019(3) 0.054(4) 0.031(3) -0.001(3) 0.002(2) -0.002(3) C2 0.039(4) 0.052(4) 0.033(3) -0.004(3) 0.003(3) -0.010(3) C3 0.019(3) 0.035(3) 0.028(3) -0.005(3) -0.005(2) 0.007(2) C4 0.032(3) 0.021(3) 0.026(3) 0.002(2) -0.005(2) -0.001(2) C5 0.032(3) 0.047(4) 0.027(3) -0.014(3) -0.003(3) 0.000(3) C6 0.024(3) 0.027(3) 0.023(3) -0.003(3) -0.008(2) 0.001(2) C7 0.024(3) 0.027(3) 0.031(3) -0.002(3) -0.006(2) 0.001(3) C8 0.018(3) 0.022(3) 0.029(3) 0.000(2) -0.009(2) 0.000(2) C9 0.028(3) 0.030(3) 0.027(3) 0.001(3) 0.002(3) 0.007(3) C10 0.023(3) 0.035(4) 0.028(3) 0.001(3) -0.003(2) -0.004(3) C11 0.027(3) 0.037(4) 0.042(4) 0.001(3) -0.001(3) -0.012(3) C12 0.028(3) 0.047(4) 0.045(4) 0.001(3) -0.006(3) -0.007(3) C13 0.027(3) 0.039(4) 0.027(3) 0.006(3) 0.004(2) -0.002(3) C14 0.031(3) 0.031(3) 0.027(3) 0.000(3) -0.001(3) -0.002(3) C15 0.034(3) 0.040(4) 0.025(3) 0.002(3) 0.000(3) -0.005(3) C16 0.045(4) 0.064(5) 0.031(3) -0.008(3) 0.005(3) 0.009(4) C17 0.041(4) 0.059(5) 0.037(3) -0.002(3) -0.012(3) 0.011(4) C18 0.041(4) 0.093(6) 0.053(4) -0.025(5) -0.006(4) 0.004(4) O1 0.026(2) 0.047(3) 0.032(2) 0.000(2) -0.0018(18) -0.009(2) O2 0.032(2) 0.043(3) 0.031(2) -0.0023(18) 0.0036(19) -0.005(2) S1 0.0239(7) 0.0366(8) 0.0290(7) -0.0055(6) -0.0008(6) -0.0030(7) S2 0.0348(8) 0.0570(11) 0.0248(7) -0.0056(7) 0.0003(7) -0.0021(9) S3 0.0268(7) 0.0436(9) 0.0290(7) -0.0084(7) -0.0040(6) -0.0080(7) S4 0.0249(7) 0.0355(9) 0.0235(7) -0.0046(6) -0.0025(6) -0.0054(6) S5 0.0333(9) 0.0692(13) 0.0430(9) -0.0176(9) -0.0031(8) 0.0164(10) S6 0.0435(10) 0.0609(11) 0.0241(7) -0.0060(8) -0.0040(7) -0.0078(9) S7 0.0353(9) 0.0713(13) 0.0302(8) -0.0070(8) -0.0067(7) 0.0153(9) _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 1.508(8) . ? C1 S1 1.799(6) . ? C1 H1A 0.9900 . ? C1 H1B 0.9900 . ? C2 S2 1.817(6) . ? C2 H2A 0.9900 . ? C2 H2B 0.9900 . ? C3 C5 1.335(8) . ? C3 C4 1.434(8) . ? C3 S2 1.761(6) . ? C4 C6 1.394(8) . ? C4 S1 1.745(6) . ? C5 S3 1.711(6) . ? C5 H5 0.9500 . ? C6 C7 1.440(8) . ? C6 S3 1.730(5) . ? C7 C8 1.366(8) . ? C7 S4 1.749(6) . ? C8 O1 1.381(6) . ? C8 C9 1.411(7) . ? C9 C10 1.345(8) . ? C9 O2 1.380(7) . ? C10 C13 1.471(8) . ? C10 S4 1.744(6) . ? C11 O1 1.408(7) . ? C11 C12 1.509(9) . ? C11 H11A 0.9900 . ? C11 H11B 0.9900 . ? C12 O2 1.437(7) . ? C12 H12A 0.9900 . ? C12 H12B 0.9900 . ? C13 C14 1.363(8) . ? C13 S5 1.711(6) . ? C14 C15 1.435(8) . ? C14 S7 1.747(6) . ? C15 C16 1.340(9) . ? C15 S6 1.761(6) . ? C16 S5 1.709(7) . ? C16 H16 0.9500 . ? C17 C18 1.497(10) . ? C17 S7 1.773(6) . ? C17 H17A 0.9900 . ? C17 H17B 0.9900 . ? C18 S6 1.810(7) . ? C18 H18A 0.9900 . ? C18 H18B 0.9900 . ? 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 112.2(4) . . ? C2 C1 H1A 109.2 . . ? S1 C1 H1A 109.2 . . ? C2 C1 H1B 109.2 . . ? S1 C1 H1B 109.2 . . ? H1A C1 H1B 107.9 . . ? C1 C2 S2 113.0(5) . . ? C1 C2 H2A 109.0 . . ? S2 C2 H2A 109.0 . . ? C1 C2 H2B 109.0 . . ? S2 C2 H2B 109.0 . . ? H2A C2 H2B 107.8 . . ? C5 C3 C4 112.0(5) . . ? C5 C3 S2 120.5(5) . . ? C4 C3 S2 127.5(4) . . ? C6 C4 C3 112.0(5) . . ? C6 C4 S1 123.6(4) . . ? C3 C4 S1 124.3(4) . . ? C3 C5 S3 114.0(4) . . ? C3 C5 H5 123.0 . . ? S3 C5 H5 123.0 . . ? C4 C6 C7 128.8(5) . . ? C4 C6 S3 110.8(4) . . ? C7 C6 S3 120.3(4) . . ? C8 C7 C6 126.5(5) . . ? C8 C7 S4 108.4(4) . . ? C6 C7 S4 125.1(4) . . ? C7 C8 O1 123.0(5) . . ? C7 C8 C9 114.9(5) . . ? O1 C8 C9 122.0(5) . . ? C10 C9 O2 123.7(5) . . ? C10 C9 C8 113.7(5) . . ? O2 C9 C8 122.6(5) . . ? C9 C10 C13 127.8(5) . . ? C9 C10 S4 110.2(4) . . ? C13 C10 S4 121.9(4) . . ? O1 C11 C12 110.8(5) . . ? O1 C11 H11A 109.5 . . ? C12 C11 H11A 109.5 . . ? O1 C11 H11B 109.5 . . ? C12 C11 H11B 109.5 . . ? H11A C11 H11B 108.1 . . ? O2 C12 C11 108.9(5) . . ? O2 C12 H12A 109.9 . . ? C11 C12 H12A 109.9 . . ? O2 C12 H12B 109.9 . . ? C11 C12 H12B 109.9 . . ? H12A C12 H12B 108.3 . . ? C14 C13 C10 129.6(5) . . ? C14 C13 S5 111.7(4) . . ? C10 C13 S5 118.5(4) . . ? C13 C14 C15 111.4(5) . . ? C13 C14 S7 122.4(4) . . ? C15 C14 S7 126.2(4) . . ? C16 C15 C14 113.1(5) . . ? C16 C15 S6 121.0(5) . . ? C14 C15 S6 125.8(5) . . ? C15 C16 S5 111.8(5) . . ? C15 C16 H16 124.1 . . ? S5 C16 H16 124.1 . . ? C18 C17 S7 115.0(5) . . ? C18 C17 H17A 108.5 . . ? S7 C17 H17A 108.5 . . ? C18 C17 H17B 108.5 . . ? S7 C17 H17B 108.5 . . ? H17A C17 H17B 107.5 . . ? C17 C18 S6 113.5(5) . . ? C17 C18 H18A 108.9 . . ? S6 C18 H18A 108.9 . . ? C17 C18 H18B 108.9 . . ? S6 C18 H18B 108.9 . . ? H18A C18 H18B 107.7 . . ? C8 O1 C11 111.4(4) . . ? C9 O2 C12 110.8(4) . . ? C4 S1 C1 100.5(3) . . ? C3 S2 C2 104.5(3) . . ? C5 S3 C6 91.2(3) . . ? C10 S4 C7 92.7(3) . . ? C16 S5 C13 92.0(3) . . ? C15 S6 C18 103.8(3) . . ? C14 S7 C17 103.1(3) . . ? _diffrn_measured_fraction_theta_max 0.998 _diffrn_reflns_theta_full 27.50 _diffrn_measured_fraction_theta_full 0.998 _refine_diff_density_max 0.701 _refine_diff_density_min -0.383 _refine_diff_density_rms 0.101