# Supplementary Material (ESI) for Journal of Materials Chemistry # This journal is © The Royal Society of Chemistry 2004 data_global _publ_contact_author_email JEAN.RONCALI@UNIV-ANGERS.FR _publ_contact_author_name 'Dr Jean Roncali' _journal_name_full J.Mater.Chem. _journal_coden_Cambridge 1145 #=============================================================================== _audit_creation_date 20-10-99 _publ_contact_author_address ; Groupe systemes conjugues lineaires CNRS UMR 6501 Universite d'Angers 2 bd Lavoisier Angers 49045 FRANCE ; _publ_section_title ; Electrogenerated Poly(thiophenes) Derivatized by Bipyridine Ligands and Metal Complexes ; loop_ _publ_author_name 'Jean Roncali' 'Magali Allain' 'Philippe Blanchard' 'Bruno Jousselme' 'Eric Levillain' ; M.Ocafrain ; data_pbf01 _database_code_depnum_ccdc_archive 'CCDC 222438' #============================================================================ # 5. CHEMICAL DATA _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_formula_moiety 'C13 H11 N O2 S3' _chemical_formula_structural ? _chemical_formula_analytical ? _chemical_formula_sum 'C13 H11 N O2 S3' _chemical_formula_weight 309.43 _chemical_melting_point ? _chemical_compound_source ? loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C ? 0.002 0.002 International_Tables_Vol_IV_Table_2.3.1 H ? 0.000 0.000 International_Tables_Vol_IV_Table_2.3.1 N ? 0.004 0.003 International_Tables_Vol_IV_Table_2.3.1 O ? 0.008 0.006 International_Tables_Vol_IV_Table_2.3.1 S ? 0.110 0.124 International_Tables_Vol_IV_Table_2.3.1 #============================================================================ # 6. CRYSTAL DATA _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M 'P 1 21/n 1' _symmetry_space_group_name_Hall '-P 2yn' loop_ _symmetry_equiv_pos_as_xyz x,y,z 1/2-x,1/2+y,1/2-z -x,-y,-z 1/2+x,1/2-y,1/2+z _cell_length_a 12.667(6) _cell_length_b 4.874(5) _cell_length_c 22.85(1) _cell_angle_alpha 90 _cell_angle_beta 103.26(3) _cell_angle_gamma 90 _cell_volume 1373(2) _cell_formula_units_Z 4 _cell_measurement_temperature 294 _cell_measurement_reflns_used 25 _cell_measurement_theta_min ? _cell_measurement_theta_max ? _cell_special_details ; ? ; _exptl_crystal_description needle _exptl_crystal_colour colorless _exptl_crystal_size_max 1 _exptl_crystal_size_mid 0.25 _exptl_crystal_size_min 0.1 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.49 _exptl_crystal_density_method none _exptl_crystal_F_000 640 _exptl_absorpt_coefficient_mu 0.534 _exptl_absorpt_correction_type refdelf_(Walker_&_Stuart,_1983) _exptl_absorpt_correction_T_min 0.4638 _exptl_absorpt_correction_T_max 1.0000 #=============================================================================== # 7. EXPERIMENTAL DATA _diffrn_special_details ; ? ; _diffrn_ambient_temperature 294 _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type Mo-K\a _diffrn_source xray_tube _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type Enraf_Nonius_CAD4 _diffrn_measurement_method w _diffrn_standards_number 3 _diffrn_standards_interval_count ? _diffrn_standards_interval_time 120 _diffrn_standards_decay_% 0 loop_ _diffrn_standard_refln_index_h _diffrn_standard_refln_index_k _diffrn_standard_refln_index_l -3 -1 6 -3 -1 -3 -2 -1 -3 _diffrn_reflns_number 4560 _diffrn_reflns_av_R_equivalents 0.06 _diffrn_reflns_av_sigmaI/netI 0.333 _diffrn_reflns_limit_h_min 0 _diffrn_reflns_limit_h_max 17 _diffrn_reflns_limit_k_min 0 _diffrn_reflns_limit_k_max 6 _diffrn_reflns_limit_l_min -32 _diffrn_reflns_limit_l_max 31 _diffrn_reflns_theta_min 2.5 _diffrn_reflns_theta_max 29.97 _reflns_number_total 4412 _reflns_number_gt 1913 _reflns_threshold_expression >3.0\s(I) _computing_data_collection CAD4_(Enraf-Nonius,_1994) _computing_cell_refinement CAD4_(Enraf-Nonius,_1994) _computing_data_reduction process_OpenMoleN_(_1997) _computing_structure_solution Direct_methods_(SIR,_Burla_et_al.,_1989) _computing_structure_refinement LSFM_OpenMoleN_(_1997) _computing_molecular_graphics ? _computing_publication_material CIFGEN_IN_OpenMoleN_(_1997) #=============================================================================== # 8. REFINEMENT DATA _refine_ls_structure_factor_coef F _refine_ls_matrix_type full _refine_ls_weighting_scheme '4Fo^2^/(\s^2^(Fo^2^) + 0.0064 Fo^4^)' _refine_ls_hydrogen_treatment noref _refine_ls_extinction_method none _refine_ls_extinction_expression ? _refine_ls_extinction_coef ? _refine_ls_abs_structure_Flack ? _refine_ls_number_reflns 1913 _refine_ls_number_parameters 172 _refine_ls_number_restraints 0 _refine_ls_number_constraints 0 _refine_ls_R_factor_all 0.133 _refine_ls_R_factor_gt 0.043 _refine_ls_wR_factor_all 0.097 _refine_ls_wR_factor_ref 0.057 _refine_ls_goodness_of_fit_all 1.625 _refine_ls_goodness_of_fit_ref 1.051 _refine_ls_shift/su_max 0.158 _refine_ls_shift/esd_mean 0.009 _refine_diff_density_max 0.376 _refine_diff_density_min -0.392 #=============================================================================== # 9. ATOMIC COORDINATES AND THERMAL PARAMETERS loop_ _atom_site_label _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_calc_flag _atom_site_calc_attached_atom _atom_site_type_symbol S1 0.38161(6) -0.1090(2) 0.20911(3) 0.0449(4) Uani ? ? S S2 0.65016(6) 0.4836(2) 0.22515(4) 0.0477(4) Uani ? ? S S3 0.47191(7) -0.0483(2) 0.08852(4) 0.0537(4) Uani ? ? S O1 0.4023(2) 0.0996(6) 0.37509(9) 0.064(1) Uani ? ? O O2 0.5597(2) 0.3806(5) 0.32347(9) 0.052(1) Uani ? ? O N 0.1914(3) 0.6881(8) 0.0004(1) 0.076(2) Uani ? ? N C1 0.3475(2) -0.1113(7) 0.2778(1) 0.051(2) Uani ? ? C C2 0.4097(2) 0.0618(7) 0.3166(1) 0.046(2) Uani ? ? C C3 0.4876(2) 0.1996(6) 0.2913(1) 0.039(1) Uani ? ? C C4 0.4831(2) 0.1338(6) 0.2326(1) 0.036(1) Uani ? ? C C5 0.5532(2) 0.2394(6) 0.1954(1) 0.038(1) Uani ? ? C C6 0.5581(2) 0.1780(7) 0.1371(1) 0.045(1) Uani ? ? C C7 0.6419(3) 0.3259(8) 0.1185(1) 0.059(2) Uani ? ? C C8 0.6963(3) 0.4961(8) 0.1604(2) 0.062(2) Uani ? ? C C9 0.4688(4) 0.319(1) 0.4032(2) 0.122(3) Uani ? ? C C10 0.5606(4) 0.384(1) 0.3852(2) 0.093(3) Uani ? ? C C11 0.3846(3) 0.1976(7) 0.0410(1) 0.053(2) Uani ? ? C C12 0.3038(3) 0.3300(7) 0.0722(1) 0.052(2) Uani ? ? C C13 0.2384(3) 0.5317(8) 0.0327(1) 0.056(2) Uani ? ? C H1 0.2918 -0.2213 0.2871 0.0665 Uiso calc C1 H H2 0.6575 0.3052 0.0799 0.0743 Uiso calc C7 H H3 0.7538 0.6107 0.1549 0.0790 Uiso calc C8 H H4 0.4902 0.2762 0.4450 0.1705 Uiso calc C9 H H5 0.4244 0.4771 0.3978 0.1705 Uiso calc C9 H H6 0.5802 0.5632 0.3993 0.1269 Uiso calc C10 H H7 0.6152 0.2593 0.4044 0.1269 Uiso calc C10 H H8 0.3454 0.1069 0.0058 0.0700 Uiso calc C11 H H9 0.4288 0.3360 0.0298 0.0700 Uiso calc C11 H H10 0.3422 0.4171 0.1081 0.0677 Uiso calc C12 H H11 0.2574 0.1938 0.0822 0.0677 Uiso calc C12 H loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_12 _atom_site_aniso_U_13 _atom_site_aniso_U_23 _atom_site_aniso_type_symbol S1 0.0445(3) 0.0424(4) 0.0481(4) -0.0077(3) 0.0080(3) -0.0020(4) S S2 0.0382(3) 0.0500(5) 0.0570(4) -0.0070(4) 0.0097(3) 0.0012(4) S S3 0.0687(5) 0.0459(4) 0.0491(4) 0.0030(4) 0.0160(3) -0.0085(4) S O1 0.066(1) 0.090(2) 0.044(1) -0.012(1) 0.0214(9) -0.001(1) O O2 0.051(1) 0.063(1) 0.045(1) -0.015(1) 0.0096(9) -0.012(1) O N 0.078(2) 0.099(3) 0.058(2) 0.020(2) 0.013(2) 0.017(2) N C1 0.045(1) 0.054(2) 0.055(2) -0.006(2) 0.014(1) 0.010(2) C C2 0.041(1) 0.055(2) 0.041(1) 0.002(1) 0.009(1) 0.004(1) C C3 0.034(1) 0.041(1) 0.043(1) 0.001(1) 0.006(1) -0.002(1) C C4 0.030(1) 0.036(1) 0.042(1) 0.000(1) 0.006(1) -0.002(1) C C5 0.032(1) 0.036(1) 0.047(1) 0.005(1) 0.008(1) 0.002(1) C C6 0.042(1) 0.045(2) 0.048(1) 0.003(1) 0.015(1) 0.001(1) C C7 0.057(2) 0.064(2) 0.057(2) 0.005(2) 0.026(1) 0.005(2) C C8 0.049(1) 0.069(2) 0.069(2) -0.007(2) 0.024(1) 0.014(2) C C9 0.128(3) 0.208(5) 0.069(2) -0.095(3) 0.050(2) -0.060(3) C C10 0.114(3) 0.128(4) 0.055(2) -0.050(3) 0.028(2) -0.027(2) C C11 0.064(2) 0.058(2) 0.040(1) -0.002(2) 0.013(1) -0.006(2) C C12 0.060(2) 0.055(2) 0.041(1) 0.003(2) 0.013(1) 0.003(2) C C13 0.055(2) 0.070(2) 0.045(2) 0.003(2) 0.012(1) -0.001(2) C # 10. MOLECULAR GEOMETRY loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_1 _geom_bond_site_symmetry_2 _geom_bond_publ_flag S1 C1 1.720(4) . . ? S1 C4 1.739(3) . . ? S2 C5 1.734(3) . . ? S2 C8 1.711(4) . . ? S3 C6 1.756(3) . . ? S3 C11 1.814(3) . . ? O1 C2 1.373(4) . . ? O1 C9 1.419(6) . . ? O2 C3 1.358(3) . . ? O2 C10 1.408(5) . . ? N C13 1.130(5) . . ? C1 C2 1.341(4) . . ? C2 C3 1.422(4) . . ? C3 C4 1.368(4) . . ? C4 C5 1.457(4) . . ? C5 C6 1.381(4) . . ? C6 C7 1.426(5) . . ? C7 C8 1.334(5) . . ? C9 C10 1.357(7) . . ? C11 C12 1.519(5) . . ? C12 C13 1.458(5) . . ? loop_ _geom_contact_atom_site_label_1 _geom_contact_atom_site_label_2 _geom_contact_distance _geom_contact_site_symmetry_1 _geom_contact_site_symmetry_2 _geom_contact_publ_flag ? ? ? ? ? ? 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_2 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C1 S1 C4 92.6(1) . . . ? C5 S2 C8 92.1(2) . . . ? C6 S3 C11 99.7(2) . . . ? C2 O1 C9 112.1(3) . . . ? C3 O2 C10 113.5(3) . . . ? S1 C1 C2 111.5(3) . . . ? O1 C2 C1 124.6(3) . . . ? O1 C2 C3 122.7(3) . . . ? C1 C2 C3 112.6(3) . . . ? O2 C3 C2 122.0(3) . . . ? O2 C3 C4 123.7(3) . . . ? C2 C3 C4 114.3(2) . . . ? S1 C4 C3 108.9(2) . . . ? S1 C4 C5 124.5(2) . . . ? C3 C4 C5 126.6(2) . . . ? S2 C5 C4 119.0(2) . . . ? S2 C5 C6 110.0(2) . . . ? C4 C5 C6 130.9(3) . . . ? S3 C6 C5 125.9(2) . . . ? S3 C6 C7 121.8(2) . . . ? C5 C6 C7 112.3(3) . . . ? C6 C7 C8 113.4(3) . . . ? S2 C8 C7 112.1(3) . . . ? O1 C9 C10 119.9(4) . . . ? O2 C10 C9 119.4(3) . . . ? S3 C11 C12 112.5(2) . . . ? C11 C12 C13 110.1(3) . . . ? N C13 C12 176.6(4) . . . ? data_(NoName) _database_code_depnum_ccdc_archive 'CCDC 222439' #=============================================================================== # 5. CHEMICAL DATA _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_formula_moiety C32H24N2O4S6 _chemical_formula_structural ? _chemical_formula_analytical ? _chemical_formula_sum C32H24N2O4S6 _chemical_formula_weight 692.94 _chemical_melting_point ? _chemical_compound_source ? loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C ? 0.002 0.002 International_Tables_Vol_IV_Table_2.3.1 H ? 0.000 0.000 International_Tables_Vol_IV_Table_2.3.1 N ? 0.004 0.003 International_Tables_Vol_IV_Table_2.3.1 O ? 0.008 0.006 International_Tables_Vol_IV_Table_2.3.1 S ? 0.110 0.124 International_Tables_Vol_IV_Table_2.3.1 #=============================================================================== # 6. CRYSTAL DATA _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M 'P 1 21/a 1' _symmetry_space_group_name_Hall '-P 2yab' loop_ _symmetry_equiv_pos_as_xyz x,y,z 1/2-x,1/2+y,-z -x,-y,-z 1/2+x,1/2-y,+z _cell_length_a 11.679(7) _cell_length_b 7.704(2) _cell_length_c 16.835(4) _cell_angle_alpha 90 _cell_angle_beta 93.35(4) _cell_angle_gamma 90 _cell_volume 1512(1) _cell_formula_units_z 2 _cell_measurement_temperature 294 _cell_measurement_reflns_used 25 _cell_measurement_theta_min 11.0 _cell_measurement_theta_max 15.0 _cell_special_details ; ? ; _exptl_crystal_description plate _exptl_crystal_colour 'light green' _exptl_crystal_size_max 1.00 _exptl_crystal_size_mid 0.50 _exptl_crystal_size_min 0.10 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.52 _exptl_crystal_density_method none _exptl_crystal_F_000 716 _exptl_absorpt_coefficient_mu 0.475 _exptl_absorpt_correction_type none _exptl_absorpt_correction_T_min 0.5891 _exptl_absorpt_correction_T_max 1.0000 #=============================================================================== # 7. EXPERIMENTAL DATA _diffrn_special_details ; ? ; _diffrn_ambient_temperature 294 _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type Mo-K\a _diffrn_radiation_source xray_tube _diffrn_radiation_monochromator graphite _diffrn_measurement_device Enraf_Nonius_CAD4 _diffrn_measurement_method \q/2\q _diffrn_standards_number 2 _diffrn_standards_interval_count ? _diffrn_standards_interval_time 120 _diffrn_standards_decay_% 0 loop_ _diffrn_standard_refln_index_h _diffrn_standard_refln_index_k _diffrn_standard_refln_index_l 0 5 4 3 -2 8 _diffrn_reflns_number 2698 _diffrn_reflns_av_R_equivalents 0.017 _diffrn_reflns_av_sigmaI/netI 0.333 _diffrn_reflns_limit_h_min 0 _diffrn_reflns_limit_h_max 13 _diffrn_reflns_limit_k_min 0 _diffrn_reflns_limit_k_max 8 _diffrn_reflns_limit_l_min -19 _diffrn_reflns_limit_l_max 19 _diffrn_reflns_theta_min 2.5 _diffrn_reflns_theta_max 23.96 _reflns_number_total 2560 _reflns_number_observed 1554 _reflns_observed_criterion >3.0\s(I) _computing_data_collection CAD4_(Enraf-Nonius,_1994) _computing_cell_refinement CAD4_(Enraf-Nonius,_1994) _computing_data_reduction process_MolEN_(Fair,_1990) _computing_structure_solution Direct_methods_(SIR,_Burla_et_al.,_1989) _computing_structure_refinement LSFM_MolEN_(Fair,_1990) _computing_molecular_graphics ? _computing_publication_material BTABLE_PTABLE_CIF_IN_MolEN_(Fair,_1990) #=============================================================================== # 8. REFINEMENT DATA _refine_ls_structure_factor_coef F _refine_ls_matrix_type full _refine_ls_weighting_scheme '4Fo^2^/(\s^2^(Fo^2^) + 0.0064 Fo^4^)' _refine_ls_hydrogen_treatment included_not_refined _refine_ls_extinction_method none _refine_ls_extinction_expression ? _refine_ls_extinction_coef ? _refine_ls_abs_structure_Flack ? _refine_ls_number_reflns 1554 _refine_ls_number_parameters 199 _refine_ls_number_restraints 0 _refine_ls_number_constraints 0 _refine_ls_abs_structure_details ; ? ; _refine_ls_R_factor_all 0.076 _refine_ls_R_factor_obs 0.040 _refine_ls_wR_factor_all 0.072 _refine_ls_wR_factor_obs 0.056 _refine_ls_goodness_of_fit_all 1.431 _refine_ls_goodness_of_fit_obs 1.179 _refine_ls_shift/esd_max 0.008 _refine_ls_shift/esd_mean 0.001 _refine_diff_density_max 0.828 _refine_diff_density_min -0.752 #=============================================================================== # 9. ATOMIC COORDINATES AND THERMAL PARAMETERS loop_ _atom_site_label _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_thermal_displace_type _atom_site_calc_flag _atom_site_calc_attached_atom _atom_site_type_symbol S1 0.19646(8) 0.0439(1) 0.20524(5) 0.0660(5) Uij ? ? S S2 0.35441(8) 0.5082(1) 0.29557(6) 0.0613(5) Uij ? ? S S3 0.42263(8) -0.0537(1) 0.30119(6) 0.0643(5) Uij ? ? S O1 0.5243(2) 0.3720(3) 0.4049(1) 0.067(1) Uij ? ? O O2 0.6629(2) 0.0803(4) 0.4566(1) 0.090(2) Uij ? ? O N 0.1079(2) -0.3358(4) -0.0117(2) 0.063(2) Uij ? ? N C1 0.0169(2) -0.4147(4) 0.0176(2) 0.050(2) Uij ? ? C C2 -0.0424(3) -0.3412(5) 0.0777(2) 0.059(2) Uij ? ? C C3 -0.0083(3) -0.1820(5) 0.1076(2) 0.065(2) Uij ? ? C C4 0.0841(3) -0.0984(4) 0.0782(2) 0.056(2) Uij ? ? C C5 0.1385(3) -0.1806(5) 0.0191(2) 0.065(2) Uij ? ? C C6 0.1234(3) 0.0757(4) 0.1087(2) 0.068(2) Uij ? ? C C7 0.2455(3) 0.2539(4) 0.2296(2) 0.054(2) Uij ? ? C C8 0.1896(3) 0.4090(4) 0.2014(2) 0.067(2) Uij ? ? C C9 0.2410(4) 0.5519(4) 0.2318(2) 0.073(2) Uij ? ? C C10 0.3387(3) 0.2862(4) 0.2806(2) 0.048(2) Uij ? ? C C11 0.4199(2) 0.1667(4) 0.3206(2) 0.050(2) Uij ? ? C C12 0.5051(3) 0.2076(4) 0.3756(2) 0.055(2) Uij ? ? C C13 0.5730(3) 0.0631(4) 0.4025(2) 0.066(2) Uij ? ? C C14 0.5376(3) -0.0847(5) 0.3672(2) 0.076(2) Uij ? ? C C15 0.6728(4) 0.2478(6) 0.4896(3) 0.115(3) Uij ? ? C C16 0.6288(4) 0.3906(6) 0.4479(3) 0.123(3) Uij ? ? C H1 0.7508 0.2673 0.5058 0.1540 Uiso calc C15 H H2 0.6303 0.2456 0.5387 0.1540 Uiso calc C15 H H3 0.6267 0.4884 0.4809 0.1718 Uiso calc C16 H H4 0.6863 0.4160 0.4079 0.1718 Uiso calc C16 H H5 0.5749 -0.1969 0.3773 0.1028 Uiso calc C14 H H6 0.2158 0.6682 0.2191 0.1008 Uiso calc C9 H H7 0.1228 0.4109 0.1650 0.0907 Uiso calc C8 H H8 0.1719 0.1306 0.0721 0.0913 Uiso calc C6 H H9 0.0571 0.1531 0.1129 0.0913 Uiso calc C6 H H10 0.2046 -0.1236 -0.0031 0.0858 Uiso calc C5 H H11 -0.0511 -0.1283 0.1495 0.0852 Uiso calc C3 H H12 -0.1067 -0.4020 0.0989 0.0774 Uiso calc C2 H loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_12 _atom_site_aniso_U_13 _atom_site_aniso_U_23 _atom_site_aniso_type_symbol S1 0.0831(5) 0.0461(4) 0.0750(5) -0.0063(4) -0.0397(4) -0.0012(4) S S2 0.0712(5) 0.0412(4) 0.0786(5) -0.0060(4) -0.0148(4) -0.0050(4) S S3 0.0704(5) 0.0452(4) 0.0834(5) 0.0042(4) -0.0279(4) -0.0045(4) S O1 0.062(1) 0.063(1) 0.077(1) -0.001(1) -0.026(1) -0.018(1) O O2 0.079(2) 0.093(2) 0.099(2) 0.015(1) -0.045(1) -0.011(1) O N 0.058(2) 0.063(2) 0.068(2) -0.011(1) -0.005(1) -0.009(1) N C1 0.047(2) 0.054(2) 0.049(2) -0.002(1) -0.017(1) -0.001(1) C C2 0.050(2) 0.069(2) 0.058(2) -0.007(2) -0.005(2) -0.008(2) C C3 0.066(2) 0.069(2) 0.060(2) 0.001(2) -0.006(2) -0.015(2) C C4 0.063(2) 0.054(2) 0.052(2) -0.000(2) -0.023(1) -0.002(1) C C5 0.054(2) 0.069(2) 0.073(2) -0.013(2) -0.012(2) -0.003(2) C C6 0.082(2) 0.056(2) 0.069(2) -0.003(2) -0.032(2) -0.004(2) C C7 0.061(2) 0.046(2) 0.057(2) 0.001(2) -0.017(1) -0.002(1) C C8 0.077(2) 0.051(2) 0.078(2) 0.013(2) -0.025(2) 0.000(2) C C9 0.090(3) 0.045(2) 0.094(3) 0.008(2) -0.021(2) 0.000(2) C C10 0.053(2) 0.039(1) 0.054(2) -0.003(1) -0.008(1) -0.003(1) C C11 0.050(2) 0.046(2) 0.054(2) -0.002(1) -0.009(1) -0.001(1) C C12 0.058(2) 0.054(2) 0.054(2) 0.002(2) -0.009(1) -0.007(2) C C13 0.061(2) 0.068(2) 0.069(2) 0.014(2) -0.020(2) -0.003(2) C C14 0.078(2) 0.059(2) 0.096(2) 0.015(2) -0.033(2) -0.002(2) C C15 0.121(3) 0.108(3) 0.118(3) -0.023(3) -0.071(2) -0.010(3) C C16 0.107(3) 0.095(3) 0.183(4) 0.024(3) -0.093(2) -0.058(3) C # 10. MOLECULAR GEOMETRY loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_1 _geom_bond_site_symmetry_2 _geom_bond_publ_flag S1 C6 1.807(4) . . ? S1 C7 1.757(3) . . ? S2 C9 1.690(4) . . ? S2 C10 1.737(3) . . ? S3 C11 1.730(3) . . ? S3 C14 1.709(4) . . ? O1 C12 1.373(4) . . ? O1 C16 1.390(5) . . ? O2 C13 1.355(4) . . ? O2 C15 1.407(6) . . ? N C1 1.343(4) . . ? N C5 1.342(4) . . ? C1 C2 1.380(4) . . ? C2 C3 1.376(5) . . ? C3 C4 1.373(5) . . ? C4 C5 1.368(5) . . ? C4 C6 1.499(4) . . ? C7 C8 1.430(4) . . ? C7 C10 1.368(4) . . ? C8 C9 1.341(5) . . ? C10 C11 1.459(4) . . ? C11 C12 1.356(4) . . ? C12 C13 1.425(5) . . ? C13 C14 1.339(5) . . ? C15 C16 1.387(7) . . ? loop_ _geom_contact_atom_site_label_1 _geom_contact_atom_site_label_2 _geom_contact_distance _geom_contact_site_symmetry_1 _geom_contact_site_symmetry_2 _geom_contact_publ_flag ? ? ? ? ? ? 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_2 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C6 S1 C7 102.5(1) . . . ? C9 S2 C10 91.8(2) . . . ? C11 S3 C14 92.1(2) . . . ? C12 O1 C16 113.7(3) . . . ? C13 O2 C15 113.4(3) . . . ? C1 N C5 117.4(3) . . . ? N C1 C2 121.7(3) . . . ? C1 C2 C3 119.1(3) . . . ? C2 C3 C4 120.2(3) . . . ? C3 C4 C5 116.9(3) . . . ? C3 C4 C6 121.9(3) . . . ? C5 C4 C6 121.2(3) . . . ? N C5 C4 124.6(3) . . . ? S1 C6 C4 107.8(2) . . . ? S1 C7 C8 123.7(2) . . . ? S1 C7 C10 123.4(2) . . . ? C8 C7 C10 112.8(3) . . . ? C7 C8 C9 112.0(3) . . . ? S2 C9 C8 113.3(3) . . . ? S2 C10 C7 110.1(2) . . . ? S2 C10 C11 119.6(2) . . . ? C7 C10 C11 130.3(3) . . . ? S3 C11 C10 123.4(2) . . . ? S3 C11 C12 109.6(2) . . . ? C10 C11 C12 126.9(3) . . . ? O1 C12 C11 123.9(3) . . . ? O1 C12 C13 122.0(3) . . . ? C11 C12 C13 114.1(3) . . . ? O2 C13 C12 122.1(3) . . . ? O2 C13 C14 126.1(3) . . . ? C12 C13 C14 111.8(3) . . . ? S3 C14 C13 112.3(3) . . . ? O2 C15 C16 120.6(4) . . . ? O1 C16 C15 118.0(4) . . . ?