# Electronic Supplementary Material (ESI) for Journal of Materials Chemistry # This journal is © The Royal Society of Chemistry 2012 data_global _journal_name_full J.Mater.Chem. _journal_coden_Cambridge 1145 _journal_volume ? _journal_page_first ? _journal_year ? _publ_contact_author_name 'Dr William G. Skene' _publ_contact_author_email w.skene@umontreal.ca _publ_section_title ; Chemical Doping of EDOT Azomethine Derivatives: Insight into the Oxidative and Hydrolytic Stability ; loop_ _publ_author_name A.Bolduc S.Dufresne W.G.Skene # Attachment '- Copie de SKEN41.CIF' data_sken41 _database_code_depnum_ccdc_archive 'CCDC 842501' #TrackingRef '- Copie de SKEN41.CIF' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C22 H20 N2 O6 S3, C1 H2 Cl2' _chemical_formula_sum 'C23 H22 Cl2 N2 O6 S3' _chemical_formula_weight 589.78 _chemical_compound_source 'Synthesized by the authors. See text' loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0181 0.0091 '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' N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' S S 0.3331 0.5567 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Cl Cl 0.3639 0.7018 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Triclinic _symmetry_space_group_name_H-M P-1 _symmetry_space_group_name_hall '-P 1' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 8.9605(2) _cell_length_b 10.9189(3) _cell_length_c 14.3701(4) _cell_angle_alpha 68.1220(10) _cell_angle_beta 84.327(2) _cell_angle_gamma 85.734(2) _cell_volume 1297.23(6) _cell_formula_units_Z 2 _cell_measurement_temperature 150(2) _cell_measurement_reflns_used 25 _cell_measurement_theta_min 15.00 _cell_measurement_theta_max 30.00 _exptl_crystal_description platelet _exptl_crystal_colour red _exptl_crystal_size_max 0.10 _exptl_crystal_size_mid 0.05 _exptl_crystal_size_min 0.04 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.510 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 608.2 _exptl_absorpt_coefficient_mu 4.884 _exptl_absorpt_correction_Type multi-scan _exptl_absorpt_correction_T_min 0.7400 _exptl_absorpt_correction_T_max 0.82500 _exptl_absorpt_process_details 'Sadabs (Sheldrick, 1996)' _diffrn_ambient_temperature 150(2) _diffrn_radiation_wavelength 1.54178 _diffrn_radiation_type CuK\a _diffrn_radiation_source 'Micro source' _diffrn_radiation_monochromator 'Helios optics' _diffrn_measurement_device_type 'Bruker Microstar' _diffrn_measurement_method \w _diffrn_detector_area_resol_mean 5.5 _diffrn_standards_number 5 _diffrn_standards_interval_count ? _diffrn_standards_interval_time 1080 _diffrn_standards_decay_% 0.00 _diffrn_reflns_number 20840 _diffrn_reflns_av_R_equivalents 0.052 _diffrn_reflns_av_sigmaI/netI 0.0449 _diffrn_reflns_limit_h_min -9 _diffrn_reflns_limit_h_max 10 _diffrn_reflns_limit_k_min -13 _diffrn_reflns_limit_k_max 13 _diffrn_reflns_limit_l_min -17 _diffrn_reflns_limit_l_max 17 _diffrn_reflns_theta_min 3.32 _diffrn_reflns_theta_max 68.22 _reflns_number_total 4754 _reflns_number_gt 2961 _reflns_threshold_expression I>2\s(I) _computing_data_collection 'SMART (Bruker, 2003)' _computing_cell_refinement 'SMART (Bruker, 2003)' _computing_data_reduction 'SAINT (Bruker, 2004)' _computing_structure_solution 'SHELXS97 (Sheldrick, 1997)' _computing_structure_refinement 'SHELXL97 (Sheldrick, 1997)' _computing_molecular_graphics 'SHELXTL (Bruker, 1997)' _computing_publication_material 'UdMX (local program)' _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^)+(0.1153P)^2^+1.4138P] 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 4100 _refine_ls_number_parameters 337 _refine_ls_number_restraints 39 _refine_ls_R_factor_all 0.0895 _refine_ls_R_factor_gt 0.0674 _refine_ls_wR_factor_ref 0.2004 _refine_ls_wR_factor_gt 0.1864 _refine_ls_goodness_of_fit_ref 1.077 _refine_ls_restrained_S_all 1.072 _refine_ls_shift/su_max 0.000 _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 S2 S 0.01308(15) 1.05162(11) 0.13190(8) 0.0310(3) Uani 1 1 d . . . S3 S 0.49233(16) 0.76687(11) 0.00634(9) 0.0373(4) Uani 1 1 d . . . S1 S -0.43795(18) 1.23743(12) 0.35710(10) 0.0467(4) Uani 1 1 d . . . O6 O 0.1336(4) 0.6835(3) 0.4345(2) 0.0354(8) Uani 1 1 d . . . O4 O -0.0952(4) 0.9217(3) 0.4698(2) 0.0368(9) Uani 1 1 d . . . O1 O 0.3635(4) 1.1077(3) -0.1820(2) 0.0356(8) Uani 1 1 d . . . N2 N 0.2285(5) 0.8643(4) 0.1199(3) 0.0289(9) Uani 1 1 d . . . O5 O 0.2107(5) 0.6253(3) 0.3032(3) 0.0450(10) Uani 1 1 d . . . O3 O -0.2120(4) 0.7598(3) 0.4484(2) 0.0358(9) Uani 1 1 d . . . O2 O 0.6197(4) 0.9950(3) -0.2656(2) 0.0380(9) Uani 1 1 d . . . C17 C -0.1246(6) 0.8485(4) 0.4192(3) 0.0297(11) Uani 1 1 d . . . N1 N -0.2012(5) 1.0960(3) 0.2712(3) 0.0303(10) Uani 1 1 d . . . C7 C -0.0444(6) 0.8971(4) 0.3163(3) 0.0262(11) Uani 1 1 d . . . C8 C 0.0716(6) 0.8298(4) 0.2767(3) 0.0275(11) Uani 1 1 d . . . C20 C 0.1470(6) 0.7025(4) 0.3362(3) 0.0304(11) Uani 1 1 d . . . C10 C 0.2641(6) 0.9421(4) 0.0279(3) 0.0289(11) Uani 1 1 d . . . H10 H 0.2093 1.0238 0.0011 0.035 Uiso 1 1 calc R . . C11 C 0.3808(6) 0.9103(4) -0.0340(3) 0.0299(11) Uani 1 1 d . . . C12 C 0.4295(6) 0.9894(4) -0.1310(3) 0.0294(12) Uani 1 1 d . . . C13 C 0.5548(6) 0.9327(4) -0.1717(3) 0.0303(12) Uani 1 1 d . . . C5 C -0.2356(6) 1.2117(4) 0.2094(4) 0.0319(12) Uani 1 1 d . . . H5 H -0.1852 1.2437 0.1441 0.038 Uiso 1 1 calc R . . C9 C 0.1155(6) 0.9012(4) 0.1771(3) 0.0282(11) Uani 1 1 d . . . C6 C -0.0878(6) 1.0161(4) 0.2482(3) 0.0293(11) Uani 1 1 d . . . C4 C -0.3498(6) 1.2934(4) 0.2379(4) 0.0339(12) Uani 1 1 d . . . C16 C 0.4560(7) 1.1845(5) -0.2704(3) 0.0393(13) Uani 1 1 d . . . H16A H 0.5373 1.2232 -0.2497 0.047 Uiso 1 1 calc R . . H16B H 0.3942 1.2578 -0.3150 0.047 Uiso 1 1 calc R . . C18 C -0.1827(7) 0.9038(6) 0.5641(4) 0.0461(15) Uani 1 1 d . . . H18A H -0.2874 0.8858 0.5583 0.055 Uiso 1 1 calc R . . H18B H -0.1843 0.9862 0.5779 0.055 Uiso 1 1 calc R . . C21 C 0.2011(7) 0.5596(5) 0.4998(4) 0.0457(14) Uani 1 1 d . . . H21A H 0.3119 0.5614 0.4887 0.055 Uiso 1 1 calc R . . H21B H 0.1677 0.4850 0.4847 0.055 Uiso 1 1 calc R . . C3 C -0.4032(6) 1.4214(5) 0.1779(4) 0.0383(13) Uani 1 1 d . . . H3 H -0.3698 1.4692 0.1098 0.046 Uiso 1 1 calc R . . C15 C 0.5240(7) 1.0987(5) -0.3274(4) 0.0401(13) Uani 1 1 d . . . H15A H 0.4428 1.0597 -0.3480 0.048 Uiso 1 1 calc R . . H15B H 0.5828 1.1537 -0.3889 0.048 Uiso 1 1 calc R . . C2 C -0.5153(7) 1.4666(5) 0.2365(4) 0.0455(15) Uani 1 1 d . . . H2 H -0.5650 1.5510 0.2112 0.055 Uiso 1 1 calc R . . C1 C -0.5451(7) 1.3794(5) 0.3312(4) 0.0457(14) Uani 1 1 d . . . H1 H -0.6181 1.3959 0.3782 0.055 Uiso 1 1 calc R . . C22 C 0.1538(8) 0.5424(6) 0.6056(4) 0.0550(17) Uani 1 1 d . . . H22A H 0.1837 0.6183 0.6191 0.082 Uiso 1 1 calc R . . H22B H 0.2019 0.4614 0.6508 0.082 Uiso 1 1 calc R . . H22C H 0.0445 0.5361 0.6168 0.082 Uiso 1 1 calc R . . C14 C 0.5995(7) 0.8138(5) -0.1062(4) 0.0379(13) Uani 1 1 d . . . H14 H 0.6814 0.7617 -0.1208 0.045 Uiso 1 1 calc R . . C19 C -0.1197(8) 0.7930(6) 0.6489(4) 0.0563(17) Uani 1 1 d . . . H19A H -0.1402 0.7089 0.6438 0.084 Uiso 1 1 calc R . . H19B H -0.1662 0.7959 0.7127 0.084 Uiso 1 1 calc R . . H19C H -0.0110 0.8010 0.6462 0.084 Uiso 1 1 calc R . . Cl1 Cl 1.108(2) 0.3307(18) 0.8902(19) 0.062(2) Uani 0.543(4) 1 d PDU A 1 Cl2 Cl 0.8543(6) 0.4927(5) 0.9385(3) 0.1126(14) Uani 0.543(4) 1 d PDU A 1 C99 C 0.939(2) 0.4271(16) 0.8563(10) 0.086(5) Uani 0.543(4) 1 d PDU A 1 H99A H 0.9609 0.5004 0.7913 0.104 Uiso 0.543(4) 1 calc PR A 1 H99B H 0.8664 0.3711 0.8448 0.104 Uiso 0.543(4) 1 calc PR A 1 Cl1' Cl 1.107(3) 0.317(2) 0.884(2) 0.062(2) Uani 0.46 1 d PDU A 2 Cl2' Cl 0.9302(7) 0.5572(6) 0.8659(4) 0.1126(14) Uani 0.46 1 d PDU A 2 C99' C 0.925(3) 0.3887(14) 0.9036(14) 0.086(5) Uani 0.46 1 d PDU A 2 H99C H 0.8526 0.3665 0.8652 0.104 Uiso 0.457(4) 1 calc PR A 2 H99D H 0.8901 0.3510 0.9758 0.104 Uiso 0.457(4) 1 calc PR A 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 S2 0.0285(9) 0.0333(6) 0.0272(6) -0.0085(4) 0.0024(5) 0.0021(5) S3 0.0385(10) 0.0351(6) 0.0339(6) -0.0103(5) 0.0050(6) 0.0022(5) S1 0.0441(11) 0.0399(7) 0.0502(8) -0.0135(6) 0.0101(7) -0.0002(6) O6 0.037(2) 0.0369(16) 0.0294(16) -0.0104(13) -0.0025(16) 0.0070(15) O4 0.036(2) 0.0485(19) 0.0317(17) -0.0230(14) 0.0117(16) -0.0121(16) O1 0.032(2) 0.0401(17) 0.0315(17) -0.0113(14) 0.0001(16) 0.0038(15) N2 0.024(3) 0.0372(19) 0.0273(19) -0.0156(16) 0.0032(18) -0.0006(17) O5 0.050(3) 0.0391(18) 0.0399(19) -0.0134(15) 0.0071(19) 0.0143(17) O3 0.035(2) 0.0357(17) 0.0351(17) -0.0116(13) 0.0035(16) -0.0074(15) O2 0.031(2) 0.0482(19) 0.0327(17) -0.0151(14) 0.0092(16) -0.0036(16) C17 0.029(3) 0.030(2) 0.031(2) -0.0113(18) -0.003(2) -0.001(2) N1 0.028(3) 0.0292(18) 0.035(2) -0.0141(16) 0.0009(19) 0.0008(17) C7 0.022(3) 0.029(2) 0.029(2) -0.0123(18) 0.002(2) -0.0025(19) C8 0.023(3) 0.031(2) 0.030(2) -0.0128(18) -0.001(2) -0.002(2) C20 0.023(3) 0.033(2) 0.034(2) -0.0110(19) 0.003(2) -0.004(2) C10 0.026(3) 0.035(2) 0.028(2) -0.0149(18) 0.000(2) -0.002(2) C11 0.029(3) 0.034(2) 0.030(2) -0.0165(19) -0.002(2) 0.000(2) C12 0.028(3) 0.034(2) 0.029(2) -0.0140(19) -0.002(2) -0.003(2) C13 0.026(4) 0.037(2) 0.030(2) -0.0157(19) 0.004(2) -0.005(2) C5 0.028(3) 0.035(2) 0.033(2) -0.0133(19) 0.001(2) 0.000(2) C9 0.026(3) 0.033(2) 0.028(2) -0.0141(18) 0.000(2) -0.001(2) C6 0.026(3) 0.030(2) 0.031(2) -0.0116(18) -0.003(2) -0.002(2) C4 0.030(4) 0.033(2) 0.040(3) -0.014(2) -0.001(2) -0.001(2) C16 0.044(4) 0.036(2) 0.031(2) -0.005(2) -0.002(2) -0.006(2) C18 0.042(4) 0.066(3) 0.038(3) -0.032(3) 0.018(3) -0.016(3) C21 0.047(4) 0.039(3) 0.039(3) -0.002(2) -0.005(3) 0.010(2) C3 0.025(4) 0.033(2) 0.059(3) -0.024(2) 0.008(3) 0.005(2) C15 0.042(4) 0.046(3) 0.029(2) -0.009(2) -0.001(2) -0.010(2) C2 0.045(4) 0.035(3) 0.053(3) -0.014(2) 0.001(3) 0.006(2) C1 0.034(4) 0.042(3) 0.063(4) -0.026(3) 0.009(3) -0.001(2) C22 0.055(5) 0.058(3) 0.041(3) -0.007(3) -0.007(3) 0.007(3) C14 0.037(4) 0.038(2) 0.040(3) -0.018(2) 0.003(3) 0.005(2) C19 0.054(5) 0.084(4) 0.033(3) -0.025(3) 0.009(3) -0.012(3) Cl1 0.0673(14) 0.053(3) 0.061(2) -0.015(2) -0.0046(12) -0.0070(19) Cl2 0.115(4) 0.135(3) 0.077(2) -0.036(2) -0.009(2) 0.049(2) C99 0.137(11) 0.065(9) 0.066(10) -0.026(8) -0.057(11) 0.019(8) Cl1' 0.0673(14) 0.053(3) 0.061(2) -0.015(2) -0.0046(12) -0.0070(19) Cl2' 0.115(4) 0.135(3) 0.077(2) -0.036(2) -0.009(2) 0.049(2) C99' 0.137(11) 0.065(9) 0.066(10) -0.026(8) -0.057(11) 0.019(8) _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_site_symmetry_1 _geom_bond_site_symmetry_2 _geom_bond_distance _geom_bond_publ_flag S2 C6 . . 1.741(5) Y S2 C9 . . 1.749(5) Y S3 C14 . . 1.717(6) Y S3 C11 . . 1.730(5) Y S1 C1 . . 1.698(6) Y S1 C4 . . 1.720(5) Y O6 C20 . . 1.343(6) Y O6 C21 . . 1.457(6) Y O4 C17 . . 1.320(5) Y O4 C18 . . 1.449(6) Y O1 C12 . . 1.349(5) Y O1 C16 . . 1.450(6) Y N2 C10 . . 1.300(6) Y N2 C9 . . 1.373(7) Y O5 C20 . . 1.198(6) Y O3 C17 . . 1.214(5) Y O2 C13 . . 1.357(6) Y O2 C15 . . 1.436(6) Y C17 C7 . . 1.498(6) Y N1 C5 . . 1.280(6) Y N1 C6 . . 1.385(7) Y C7 C6 . . 1.360(6) Y C7 C8 . . 1.423(7) Y C8 C9 . . 1.384(6) Y C8 C20 . . 1.486(6) Y C10 C11 . . 1.413(7) Y C10 H10 . . 0.95 ? C11 C12 . . 1.386(6) Y C12 C13 . . 1.422(7) Y C13 C14 . . 1.348(7) Y C5 C4 . . 1.436(7) Y C5 H5 . . 0.95 ? C4 C3 . . 1.418(7) Y C16 C15 . . 1.519(8) Y C16 H16a . . 0.99 ? C16 H16b . . 0.99 ? C18 C19 . . 1.485(8) Y C18 H18a . . 0.99 ? C18 H18b . . 0.99 ? C21 C22 . . 1.483(8) Y C21 H21a . . 0.99 ? C21 H21b . . 0.99 ? C3 C2 . . 1.425(8) Y C3 H3 . . 0.95 ? C15 H15a . . 0.99 ? C15 H15b . . 0.99 ? C2 C1 . . 1.353(8) Y C2 H2 . . 0.95 ? C1 H1 . . 0.95 ? C22 H22a . . 0.98 ? C22 H22b . . 0.98 ? C22 H22c . . 0.98 ? C14 H14 . . 0.95 ? C19 H19a . . 0.98 ? C19 H19b . . 0.98 ? C19 H19c . . 0.98 ? Cl1 C99 . . 1.782(15) Y Cl2 C99 . . 1.691(14) Y C99 H99a . . 0.99 ? C99 H99b . . 0.99 ? Cl1' C99' . . 1.797(17) Y Cl2' C99' . . 1.716(15) Y C99' H99c . . 0.99 ? C99' H99d . . 0.99 ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_2 _geom_angle_site_symmetry_3 _geom_angle _geom_angle_publ_flag C6 S2 C9 . . . 90.9(2) Y C14 S3 C11 . . . 91.8(2) Y C1 S1 C4 . . . 91.3(3) Y C20 O6 C21 . . . 114.9(4) Y C17 O4 C18 . . . 118.1(4) Y C12 O1 C16 . . . 112.2(4) Y C10 N2 C9 . . . 120.4(4) Y C13 O2 C15 . . . 112.5(4) Y O3 C17 O4 . . . 125.2(5) Y O3 C17 C7 . . . 124.1(4) Y O4 C17 C7 . . . 110.5(4) Y C5 N1 C6 . . . 122.4(4) Y C6 C7 C8 . . . 113.3(4) Y C6 C7 C17 . . . 119.1(5) Y C8 C7 C17 . . . 127.5(4) Y C9 C8 C7 . . . 112.3(4) Y C9 C8 C20 . . . 122.9(5) Y C7 C8 C20 . . . 124.7(4) Y O5 C20 O6 . . . 123.5(4) Y O5 C20 C8 . . . 125.9(4) Y O6 C20 C8 . . . 110.7(4) Y N2 C10 C11 . . . 122.9(4) Y N2 C10 H10 . . . 118.6 ? C11 C10 H10 . . . 118.6 ? C12 C11 C10 . . . 126.5(4) Y C12 C11 S3 . . . 110.1(4) Y C10 C11 S3 . . . 123.3(3) Y O1 C12 C11 . . . 123.3(5) Y O1 C12 C13 . . . 123.5(4) Y C11 C12 C13 . . . 113.2(4) Y C14 C13 O2 . . . 125.6(5) Y C14 C13 C12 . . . 112.2(4) Y O2 C13 C12 . . . 122.2(4) Y N1 C5 C4 . . . 120.6(5) Y N1 C5 H5 . . . 119.7 ? C4 C5 H5 . . . 119.7 ? N2 C9 C8 . . . 125.7(4) Y N2 C9 S2 . . . 122.8(3) Y C8 C9 S2 . . . 111.4(4) Y C7 C6 N1 . . . 122.3(4) Y C7 C6 S2 . . . 112.1(4) Y N1 C6 S2 . . . 125.6(3) Y C3 C4 C5 . . . 127.5(5) Y C3 C4 S1 . . . 112.6(4) Y C5 C4 S1 . . . 119.8(3) Y O1 C16 C15 . . . 110.8(4) Y O1 C16 H16A . . . 109.5 ? C15 C16 H16A . . . 109.5 ? O1 C16 H16B . . . 109.5 ? C15 C16 H16B . . . 109.5 ? H16A C16 H16B . . . 108.1 ? O4 C18 C19 . . . 111.5(5) Y O4 C18 H18A . . . 109.3 ? C19 C18 H18A . . . 109.3 ? O4 C18 H18B . . . 109.3 ? C19 C18 H18B . . . 109.3 ? H18A C18 H18B . . . 108 ? O6 C21 C22 . . . 108.3(5) Y O6 C21 H21A . . . 110 ? C22 C21 H21A . . . 110 ? O6 C21 H21B . . . 110 ? C22 C21 H21B . . . 110 ? H21A C21 H21B . . . 108.4 ? C4 C3 C2 . . . 108.7(5) Y C4 C3 H3 . . . 125.7 ? C2 C3 H3 . . . 125.7 ? O2 C15 C16 . . . 110.5(4) Y O2 C15 H15A . . . 109.5 ? C16 C15 H15A . . . 109.5 ? O2 C15 H15B . . . 109.5 ? C16 C15 H15B . . . 109.5 ? H15A C15 H15B . . . 108.1 ? C1 C2 C3 . . . 114.5(5) Y C1 C2 H2 . . . 122.7 ? C3 C2 H2 . . . 122.7 ? C2 C1 S1 . . . 112.8(5) Y C2 C1 H1 . . . 123.6 ? S1 C1 H1 . . . 123.6 ? C21 C22 H22A . . . 109.5 ? C21 C22 H22B . . . 109.5 ? H22A C22 H22B . . . 109.5 ? C21 C22 H22C . . . 109.5 ? H22A C22 H22C . . . 109.5 ? H22B C22 H22C . . . 109.5 ? C13 C14 S3 . . . 112.7(4) Y C13 C14 H14 . . . 123.7 ? S3 C14 H14 . . . 123.7 ? C18 C19 H19A . . . 109.5 ? C18 C19 H19B . . . 109.5 ? H19A C19 H19B . . . 109.5 ? C18 C19 H19C . . . 109.5 ? H19A C19 H19C . . . 109.5 ? H19B C19 H19C . . . 109.5 ? CL2 C99 CL1 . . . 117.30(11) Y CL2 C99 H99A . . . 108 ? CL1 C99 H99A . . . 108 ? CL2 C99 H99B . . . 108 ? CL1 C99 H99B . . . 108 ? H99A C99 H99B . . . 107.2 ? CL2' C99' CL1' . . . 111.30(14) Y CL2' C99' H99C . . . 109.4 ? CL1' C99' H99C . . . 109.4 ? CL2' C99' H99D . . . 109.4 ? CL1' C99' H99D . . . 109.4 ? H99C C99' H99D . . . 108 ? 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_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion _geom_torsion_publ_flag C18 O4 C17 O3 . . . . -5.7(7) Y C18 O4 C17 C7 . . . . 169.6(4) Y O3 C17 C7 C6 . . . . 106.9(5) Y O4 C17 C7 C6 . . . . -68.5(5) Y O3 C17 C7 C8 . . . . -69.6(7) Y O4 C17 C7 C8 . . . . 115.0(5) Y C6 C7 C8 C9 . . . . 0.3(5) Y C17 C7 C8 C9 . . . . 177.0(4) Y C6 C7 C8 C20 . . . . 175.7(4) Y C17 C7 C8 C20 . . . . -7.6(7) Y C21 O6 C20 O5 . . . . -0.9(7) Y C21 O6 C20 C8 . . . . 178.6(4) Y C9 C8 C20 O5 . . . . -28.0(8) Y C7 C8 C20 O5 . . . . 157.0(5) Y C9 C8 C20 O6 . . . . 152.5(4) Y C7 C8 C20 O6 . . . . -22.4(6) Y C9 N2 C10 C11 . . . . 179.0(4) Y N2 C10 C11 C12 . . . . -177.4(4) Y N2 C10 C11 S3 . . . . -1.6(6) Y C14 S3 C11 C12 . . . . -0.5(4) Y C14 S3 C11 C10 . . . . -176.9(4) Y C16 O1 C12 C11 . . . . 165.6(4) Y C16 O1 C12 C13 . . . . -15.1(6) Y C10 C11 C12 O1 . . . . -3.8(7) Y S3 C11 C12 O1 . . . . 179.9(3) Y C10 C11 C12 C13 . . . . 176.8(4) Y S3 C11 C12 C13 . . . . 0.6(5) Y C15 O2 C13 C14 . . . . 162.8(5) Y C15 O2 C13 C12 . . . . -18.0(6) Y O1 C12 C13 C14 . . . . -179.7(4) Y C11 C12 C13 C14 . . . . -0.3(6) Y O1 C12 C13 O2 . . . . 1.0(7) Y C11 C12 C13 O2 . . . . -179.6(4) Y C6 N1 C5 C4 . . . . -177.4(4) Y C10 N2 C9 C8 . . . . -177.2(4) Y C10 N2 C9 S2 . . . . 0.1(6) Y C7 C8 C9 N2 . . . . 177.4(4) Y C20 C8 C9 N2 . . . . 1.9(7) Y C7 C8 C9 S2 . . . . -0.2(5) Y C20 C8 C9 S2 . . . . -175.6(3) Y C6 S2 C9 N2 . . . . -177.6(4) Y C6 S2 C9 C8 . . . . 0.0(3) Y C8 C7 C6 N1 . . . . 178.7(4) Y C17 C7 C6 N1 . . . . 1.7(6) Y C8 C7 C6 S2 . . . . -0.4(5) Y C17 C7 C6 S2 . . . . -177.4(3) Y C5 N1 C6 C7 . . . . 175.3(4) Y C5 N1 C6 S2 . . . . -5.7(6) Y C9 S2 C6 C7 . . . . 0.2(4) Y C9 S2 C6 N1 . . . . -178.8(4) Y N1 C5 C4 C3 . . . . -178.3(5) Y N1 C5 C4 S1 . . . . 1.7(6) Y C1 S1 C4 C3 . . . . -0.2(4) Y C1 S1 C4 C5 . . . . 179.8(4) Y C12 O1 C16 C15 . . . . 43.8(5) Y C17 O4 C18 C19 . . . . 84.6(6) Y C20 O6 C21 C22 . . . . -170.0(5) Y C5 C4 C3 C2 . . . . -179.3(5) Y S1 C4 C3 C2 . . . . 0.7(6) Y C13 O2 C15 C16 . . . . 46.7(5) Y O1 C16 C15 O2 . . . . -61.7(5) Y C4 C3 C2 C1 . . . . -1.1(7) Y C3 C2 C1 S1 . . . . 0.9(7) Y C4 S1 C1 C2 . . . . -0.4(5) Y O2 C13 C14 S3 . . . . 179.2(3) Y C12 C13 C14 S3 . . . . -0.1(5) Y C11 S3 C14 C13 . . . . 0.4(4) Y _diffrn_measured_fraction_theta_max 0.952 _diffrn_reflns_theta_full 68.22 _diffrn_measured_fraction_theta_full 0.952 _refine_diff_density_max 1.275 _refine_diff_density_min -1.275 _refine_diff_density_rms 0.093