# Supplementary Material (ESI) for Journal of Materials Chemistry # This journal is © The Royal Society of Chemistry 2002 data_s92 _database_code_CSD 158840 _journal_coden_Cambridge 1145 _publ_requested_journal 'Journal of Materials Chemistry' loop_ _publ_author_name 'Coles, Simon J.' 'Cravino, Antonio' 'Hursthouse, Michael B.' 'Khan, Tahir' 'Light, Mark E.' 'McDouall, Joseph J.W.' 'Neugebauer, Helmut' 'Pozo-Gonzalo, Cristina' 'Roberts, Donna M.' 'Sariciftci, N Serdar' 'Skabara, Peter' _publ_contact_author_name 'Dr Peter Skabara' _publ_contact_author_address ; Department of Chemistry University of Manchester Oxford Road Manchester M13 9PL UNITED KINGDOM ; _publ_contact_author_email 'PETER.SKABARA@MAN.AC.UK' _publ_section_title ; Synthesis and electropolymerisation of 3',4'-Bis(alkylsulfanyl)terthiophenes and the significance of the fused dithiin ring in 2,5-bithienyl-3,4-ethylenedithiothiophene (BT-EDTT) ; _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_formula_moiety ? _chemical_formula_sum 'C14 H10 S5' _chemical_formula_weight 338.52 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 Orthorhombic _symmetry_space_group_name_H-M Cmc21 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, z+1/2' 'x, -y, z+1/2' '-x, y, z' 'x+1/2, y+1/2, z' '-x+1/2, -y+1/2, z+1/2' 'x+1/2, -y+1/2, z+1/2' '-x+1/2, y+1/2, z' _cell_length_a 20.6948(7) _cell_length_b 8.7890(3) _cell_length_c 7.7472(3) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 1409.11(9) _cell_formula_units_Z 4 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 6285 _cell_measurement_theta_min 3.64 _cell_measurement_theta_max 25.01 _exptl_crystal_description Blocks _exptl_crystal_colour Orange _exptl_crystal_size_max 0.15 _exptl_crystal_size_mid 0.1 _exptl_crystal_size_min 0.1 _exptl_crystal_density_meas 'not measured' _exptl_crystal_density_diffrn 1.596 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 696 _exptl_absorpt_coefficient_mu 0.803 _exptl_absorpt_correction_type 'multi-scan' _exptl_absorpt_correction_T_min 0.9393 _exptl_absorpt_correction_T_max 0.9843 _exptl_special_details ; SORTAV; Blessing, 1997 ; _diffrn_ambient_temperature 293(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 'Phi and Omega scans to fill asymmetric unit' _diffrn_detector_area_resol_mean '9.091 pixels/mm' _diffrn_standards_number 'not measured' _diffrn_standards_interval_count na _diffrn_standards_interval_time na _diffrn_standards_decay_% na _diffrn_reflns_number 6285 _diffrn_reflns_av_R_equivalents 0.0276 _diffrn_reflns_av_sigmaI/netI 0.0269 _diffrn_reflns_limit_h_min -24 _diffrn_reflns_limit_h_max 24 _diffrn_reflns_limit_k_min -10 _diffrn_reflns_limit_k_max 10 _diffrn_reflns_limit_l_min -9 _diffrn_reflns_limit_l_max 9 _diffrn_reflns_theta_min 3.64 _diffrn_reflns_theta_max 25.01 _reflns_number_total 1246 _reflns_number_gt 1222 _reflns_threshold_expression >2sigma(I) _computing_data_collection ; DENZO (Otwinowski and Minor, 1997), COLLECT (Hooft, 1998) ; _computing_cell_refinement ; DENZO (Otwinowski and Minor, 1997), COLLECT (Hooft, 1998) ; _computing_data_reduction ; DENZO (Otwinowski and Minor, 1997), COLLECT (Hooft, 1998), MAXUS (Mackay et al., 1998) ; _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'ORTEP-III (Burnett et al., 1996)' _computing_publication_material 'WINGX (Farrugia (1998)' _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 w=1/[\s^2^(Fo^2^)+(0.0314P)^2^+0.9895P] 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 0.0033(10) _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 0.03(9) _refine_ls_number_reflns 1246 _refine_ls_number_parameters 98 _refine_ls_number_restraints 1 _refine_ls_R_factor_all 0.0231 _refine_ls_R_factor_gt 0.0224 _refine_ls_wR_factor_ref 0.0583 _refine_ls_wR_factor_gt 0.0579 _refine_ls_goodness_of_fit_ref 1.047 _refine_ls_restrained_S_all 1.047 _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_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group S3 S 0.91480(3) 0.93577(5) 0.05319(8) 0.02761(18) Uani 1 d . . . S1 S 0.84920(3) 1.43856(6) -0.09728(8) 0.02858(18) Uani 1 d . . . S2 S 1.0000 1.37650(7) 0.03362(11) 0.01926(19) Uani 1 d S . . C6 C 0.96548(9) 1.0963(2) 0.0474(3) 0.0176(4) Uani 1 d . . . C5 C 0.93984(8) 1.2406(2) 0.0387(3) 0.0183(4) Uani 1 d . . . C3 C 0.82121(9) 1.2361(2) 0.1316(3) 0.0239(5) Uani 1 d . . . H3 H 0.8241 1.1571 0.2111 0.029 Uiso 1 calc R . . C4 C 0.87245(9) 1.2895(2) 0.0341(3) 0.0194(4) Uani 1 d . . . C1 C 0.77131(11) 1.4299(2) -0.0234(3) 0.0297(5) Uani 1 d . . . H1 H 0.7384 1.4945 -0.0598 0.036 Uiso 1 calc R . . C2 C 0.76336(10) 1.3181(2) 0.0941(3) 0.0279(5) Uani 1 d . . . H2 H 0.7239 1.2965 0.1458 0.033 Uiso 1 calc R . . C7A C 0.9692(3) 0.7883(6) -0.0083(11) 0.0310(11) Uani 0.50 d P . . H7A1 H 0.9473 0.6913 0.0040 0.037 Uiso 0.50 calc PR . . H7A2 H 0.9798 0.8009 -0.1294 0.037 Uiso 0.50 calc PR . . C7B C 0.9688(3) 0.7824(7) 0.0934(10) 0.0281(11) Uani 0.50 d P . . H7B1 H 0.9566 0.7438 0.2061 0.034 Uiso 0.50 calc PR . . H7B2 H 0.9566 0.7041 0.0114 0.034 Uiso 0.50 calc PR . . 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 S3 0.0225(3) 0.0142(3) 0.0462(4) 0.0002(3) 0.0004(2) -0.00390(17) S1 0.0275(3) 0.0245(3) 0.0338(3) 0.0052(3) -0.0024(2) 0.0062(2) S2 0.0195(3) 0.0109(3) 0.0274(4) 0.0001(3) 0.000 0.000 C6 0.0196(9) 0.0140(8) 0.0192(9) -0.0005(10) 0.0004(9) -0.0015(7) C5 0.0183(9) 0.0148(9) 0.0217(9) 0.0003(10) -0.0011(9) -0.0026(7) C3 0.0166(10) 0.0179(10) 0.0373(12) -0.0033(10) -0.0006(9) -0.0006(8) C4 0.0196(9) 0.0143(8) 0.0242(10) -0.0024(9) -0.0019(9) 0.0018(7) C1 0.0248(11) 0.0278(11) 0.0367(13) -0.0069(9) -0.0075(10) 0.0087(9) C2 0.0170(10) 0.0257(12) 0.0410(14) -0.0079(10) 0.0004(9) 0.0012(8) C7A 0.035(3) 0.010(2) 0.048(4) -0.005(3) -0.008(3) -0.002(2) C7B 0.036(3) 0.017(3) 0.031(3) 0.006(3) 0.005(3) -0.0007(19) _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 S3 C6 1.7586(18) . ? S3 C7B 1.778(6) . ? S3 C7A 1.782(6) . ? S1 C1 1.712(2) . ? S1 C4 1.727(2) . ? S2 C5 1.7259(18) . ? S2 C5 1.7259(17) 4_755 ? C6 C5 1.376(2) . ? C6 C6 1.429(4) 4_755 ? C5 C4 1.460(2) . ? C3 C4 1.384(3) . ? C3 C2 1.427(3) . ? C1 C2 1.350(3) . ? C7A C7B 1.507(5) 4_755 ? C7B C7B 1.293(11) 4_755 ? 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 C6 S3 C7B 103.77(19) . . ? C6 S3 C7A 101.55(19) . . ? C7B S3 C7A 25.63(18) . . ? C1 S1 C4 91.81(10) . . ? C5 S2 C5 92.33(12) . 4_755 ? C5 C6 C6 112.68(10) . 4_755 ? C5 C6 S3 120.70(14) . . ? C6 C6 S3 126.61(6) 4_755 . ? C6 C5 C4 129.87(16) . . ? C6 C5 S2 111.15(13) . . ? C4 C5 S2 118.98(13) . . ? C4 C3 C2 111.1(2) . . ? C3 C4 C5 128.2(2) . . ? C3 C4 S1 111.45(14) . . ? C5 C4 S1 120.26(15) . . ? C2 C1 S1 111.87(16) . . ? C1 C2 C3 113.8(2) . . ? C7B C7A S3 115.0(4) 4_755 . ? C7B C7B S3 128.91(17) 4_755 . ? _diffrn_measured_fraction_theta_max 0.496 _diffrn_reflns_theta_full 25.01 _diffrn_measured_fraction_theta_full 0.496 _refine_diff_density_max 0.237 _refine_diff_density_min -0.182 _refine_diff_density_rms 0.045 data_s92_b _database_code_CSD 171910 _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C15 H12 S5' _chemical_formula_weight 352.55 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 Orthorhombic _symmetry_space_group_name_H-M Pbca 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' '-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 15.721(3) _cell_length_b 8.8601(18) _cell_length_c 21.597(4) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 3008.2(10) _cell_formula_units_Z 8 _cell_measurement_temperature 150(2) _cell_measurement_reflns_used 33669 _cell_measurement_theta_min 2.91 _cell_measurement_theta_max 27.48 _exptl_crystal_description block _exptl_crystal_colour orange _exptl_crystal_size_max 0.30 _exptl_crystal_size_mid 0.30 _exptl_crystal_size_min 0.25 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.557 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1456 _exptl_absorpt_coefficient_mu 0.755 _exptl_absorpt_correction_type multi-scans _exptl_absorpt_correction_T_min 0.8051 _exptl_absorpt_correction_T_max 0.8336 _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 '\\f and \\w 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 14827 _diffrn_reflns_av_R_equivalents 0.0400 _diffrn_reflns_av_sigmaI/netI 0.0456 _diffrn_reflns_limit_h_min -20 _diffrn_reflns_limit_h_max 20 _diffrn_reflns_limit_k_min -11 _diffrn_reflns_limit_k_max 11 _diffrn_reflns_limit_l_min -27 _diffrn_reflns_limit_l_max 27 _diffrn_reflns_theta_min 3.21 _diffrn_reflns_theta_max 27.47 _reflns_number_total 3385 _reflns_number_gt 2642 _reflns_threshold_expression >2sigma(I) _computing_data_collection ? _computing_cell_refinement 'DENZO, COLLECT' _computing_data_reduction 'DENZO, COLLECT' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _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^)+(0.0387P)^2^+1.3629P] 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 0.0011(4) _refine_ls_extinction_expression 'Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^' _refine_ls_number_reflns 3385 _refine_ls_number_parameters 200 _refine_ls_number_restraints 6 _refine_ls_R_factor_all 0.0508 _refine_ls_R_factor_gt 0.0337 _refine_ls_wR_factor_ref 0.0854 _refine_ls_wR_factor_gt 0.0768 _refine_ls_goodness_of_fit_ref 1.022 _refine_ls_restrained_S_all 1.021 _refine_ls_shift/su_max 0.340 _refine_ls_shift/su_mean 0.034 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 0.04078(13) -0.0250(2) 0.60120(9) 0.0230(4) Uani 1 1 d . . . H1A H -0.0020 -0.0002 0.6333 0.028 Uiso 1 1 calc R . . H1B H 0.0163 -0.1052 0.5747 0.028 Uiso 1 1 calc R . . C2 C 0.11950(13) -0.0875(2) 0.63312(9) 0.0232(4) Uani 1 1 d . . . H2A H 0.1077 -0.1927 0.6460 0.028 Uiso 1 1 calc R . . H2B H 0.1666 -0.0904 0.6028 0.028 Uiso 1 1 calc R . . C3 C 0.14854(14) 0.0007(2) 0.68925(9) 0.0242(4) Uani 1 1 d . . . H3A H 0.1917 -0.0600 0.7115 0.029 Uiso 1 1 calc R . . H3B H 0.0993 0.0136 0.7174 0.029 Uiso 1 1 calc R . . C4 C 0.10373(12) 0.3002(2) 0.66117(8) 0.0188(4) Uani 1 1 d . . . C5 C 0.04927(12) 0.2880(2) 0.60823(8) 0.0188(4) Uani 1 1 d . . . C6 C 0.08504(12) 0.4222(2) 0.69780(8) 0.0196(4) Uani 1 1 d . C . C7 C 0.12168(13) 0.4726(2) 0.75620(9) 0.0228(4) Uani 1 1 d . . . C8 C 0.18674(15) 0.4860(3) 0.85655(10) 0.0416(6) Uani 1 1 d . . . H8 H 0.2146 0.4557 0.8935 0.050 Uiso 1 1 calc R A 1 C9 C 0.16051(16) 0.6262(3) 0.84304(12) 0.0430(7) Uani 1 1 d . C . H9 H 0.1656 0.7107 0.8699 0.052 Uiso 1 1 calc R B 2 C11 C -0.00862(12) 0.4039(2) 0.60380(8) 0.0192(4) Uani 1 1 d . C . C12 C -0.07415(12) 0.4393(2) 0.55864(9) 0.0205(4) Uani 1 1 d . . . C13 C -0.11872(13) 0.5763(2) 0.55465(9) 0.0243(4) Uani 1 1 d . . . H13 H -0.1084 0.6613 0.5804 0.029 Uiso 1 1 calc R . . C14 C -0.18111(14) 0.5714(3) 0.50725(10) 0.0307(5) Uani 1 1 d . . . H14 H -0.2183 0.6532 0.4985 0.037 Uiso 1 1 calc R . . C15 C -0.18264(14) 0.4402(3) 0.47589(10) 0.0300(5) Uani 1 1 d . . . H15 H -0.2208 0.4193 0.4429 0.036 Uiso 1 1 calc R . . S1 S 0.05808(3) 0.14198(5) 0.55366(2) 0.02326(14) Uani 1 1 d . . . S2 S 0.19341(3) 0.18544(6) 0.67342(2) 0.02254(14) Uani 1 1 d . . . S3 S 0.00237(3) 0.52574(5) 0.66615(2) 0.02179(14) Uani 1 1 d . . . S5 S -0.10827(4) 0.31581(6) 0.50228(2) 0.03009(16) Uani 1 1 d . . . C10 C 0.1642(9) 0.3844(15) 0.8026(7) 0.025(3) Uani 0.50 1 d PU C 1 H10 H 0.1762 0.2795 0.7999 0.029 Uiso 0.50 1 calc PR C 1 S4' S 0.1702(2) 0.3588(4) 0.80648(15) 0.0300(6) Uani 0.50 1 d P C 1 C10' C 0.1204(13) 0.6307(18) 0.7770(9) 0.053(5) Uani 0.50 1 d P C 2 H10' H 0.0999 0.7163 0.7551 0.063 Uiso 0.50 1 calc PR C 2 S4 S 0.1154(3) 0.6497(4) 0.7804(2) 0.0276(7) Uani 0.50 1 d P C 2 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 0.0214(11) 0.0196(10) 0.0278(10) -0.0028(8) -0.0011(8) -0.0023(8) C2 0.0243(12) 0.0190(9) 0.0264(10) 0.0015(8) -0.0010(8) 0.0014(8) C3 0.0263(12) 0.0228(10) 0.0235(10) 0.0010(8) 0.0000(8) 0.0023(9) C4 0.0183(11) 0.0178(9) 0.0203(9) 0.0004(7) 0.0003(7) -0.0021(7) C5 0.0198(11) 0.0187(9) 0.0179(9) -0.0006(7) 0.0017(7) -0.0004(8) C6 0.0182(10) 0.0204(9) 0.0202(9) -0.0011(8) 0.0017(8) -0.0025(8) C7 0.0204(11) 0.0253(11) 0.0225(10) -0.0068(8) 0.0025(8) -0.0037(8) C8 0.0256(14) 0.0740(19) 0.0253(11) -0.0057(12) -0.0065(10) -0.0014(12) C9 0.0342(15) 0.0484(15) 0.0463(14) -0.0288(12) 0.0147(11) -0.0174(12) C11 0.0192(11) 0.0199(9) 0.0183(9) -0.0001(8) 0.0024(7) -0.0026(7) C12 0.0200(11) 0.0205(9) 0.0209(9) 0.0019(8) 0.0030(8) -0.0018(8) C13 0.0212(12) 0.0294(11) 0.0223(10) -0.0012(9) -0.0007(8) 0.0059(9) C14 0.0236(12) 0.0315(12) 0.0369(12) 0.0089(10) -0.0002(9) 0.0071(9) C15 0.0245(12) 0.0376(12) 0.0279(11) 0.0069(10) -0.0063(9) -0.0012(10) S1 0.0299(3) 0.0215(3) 0.0184(2) -0.00394(19) -0.00345(19) 0.0047(2) S2 0.0176(3) 0.0230(3) 0.0269(3) -0.0044(2) -0.00276(19) 0.00103(19) S3 0.0232(3) 0.0195(2) 0.0227(3) -0.00364(19) -0.00013(19) 0.00157(19) S5 0.0324(3) 0.0277(3) 0.0302(3) -0.0018(2) -0.0102(2) 0.0023(2) C10 0.025(3) 0.024(3) 0.025(3) -0.0006(10) -0.0002(10) 0.0007(10) S4' 0.0334(11) 0.0343(13) 0.0223(9) -0.0044(8) -0.0096(6) 0.0058(9) C10' 0.040(7) 0.089(12) 0.029(7) 0.014(7) 0.003(5) 0.000(7) S4 0.0325(14) 0.0239(8) 0.0265(12) -0.0075(8) 0.0055(9) -0.0059(7) _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 1.521(3) . ? C1 S1 1.8212(19) . ? C2 C3 1.513(3) . ? C3 S2 1.815(2) . ? C4 C6 1.371(3) . ? C4 C5 1.432(3) . ? C4 S2 1.758(2) . ? C5 C11 1.375(3) . ? C5 S1 1.7556(18) . ? C6 C7 1.457(3) . ? C6 S3 1.731(2) . ? C7 C10' 1.471(15) . ? C7 C10 1.436(12) . ? C7 S4' 1.667(4) . ? C7 S4 1.656(4) . ? C8 C9 1.341(4) . ? C8 C10 1.514(15) . ? C9 C10' 1.56(2) . ? C11 C12 1.453(3) . ? C11 S3 1.7345(19) . ? C12 C13 1.404(3) . ? C12 S5 1.722(2) . ? C13 C14 1.418(3) . ? C14 C15 1.346(3) . ? C15 S5 1.705(2) . ? 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 115.46(14) . . ? C3 C2 C1 114.85(16) . . ? C2 C3 S2 115.63(14) . . ? C6 C4 C5 113.07(17) . . ? C6 C4 S2 122.74(15) . . ? C5 C4 S2 123.76(14) . . ? C11 C5 C4 113.24(16) . . ? C11 C5 S1 123.76(14) . . ? C4 C5 S1 122.97(14) . . ? C4 C6 C7 131.03(18) . . ? C4 C6 S3 110.53(14) . . ? C7 C6 S3 118.44(14) . . ? C6 C7 C10' 123.4(9) . . ? C6 C7 C10 128.4(6) . . ? C10' C7 C10 108.1(11) . . ? C6 C7 S4' 124.01(19) . . ? C10' C7 S4' 112.6(9) . . ? C10 C7 S4' 4.4(7) . . ? C6 C7 S4 122.7(2) . . ? C10' C7 S4 2.7(9) . . ? C10 C7 S4 108.8(6) . . ? S4' C7 S4 113.2(2) . . ? C9 C8 C10 108.1(5) . . ? C8 C9 C10' 110.3(6) . . ? C5 C11 C12 132.61(17) . . ? C5 C11 S3 110.17(14) . . ? C12 C11 S3 117.23(14) . . ? C13 C12 C11 125.57(18) . . ? C13 C12 S5 110.51(15) . . ? C11 C12 S5 123.93(15) . . ? C12 C13 C14 111.30(19) . . ? C15 C14 C13 113.7(2) . . ? C14 C15 S5 112.22(16) . . ? C5 S1 C1 102.03(9) . . ? C4 S2 C3 103.78(10) . . ? C6 S3 C11 92.96(9) . . ? C15 S5 C12 92.24(11) . . ? C8 C10 C7 108.8(8) . . ? C7 C10' C9 104.4(12) . . ? _diffrn_measured_fraction_theta_max 0.980 _diffrn_reflns_theta_full 27.47 _diffrn_measured_fraction_theta_full 0.980 _refine_diff_density_max 0.394 _refine_diff_density_min -0.399 _refine_diff_density_rms 0.066