# Supplementary Material (ESI) for Journal of Materials Chemistry # This journal is (c) The Royal Society of Chemistry 2010 ####################################################################### # # Cambridge Crystallographic Data Centre # CCDC # data_1 _database_code_depnum_ccdc_archive 'CCDC 774474' #TrackingRef '991_web_deposit_cif_file_0_Hongkuntian_1271933456.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C34 H30 N4 S2' _chemical_formula_weight 558.74 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' N N 0.0061 0.0033 '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 Triclinic _symmetry_space_group_name_H-M P-1 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 4.7904(7) _cell_length_b 9.2698(14) _cell_length_c 16.959(3) _cell_angle_alpha 74.549(2) _cell_angle_beta 89.651(2) _cell_angle_gamma 86.261(2) _cell_volume 724.29(19) _cell_formula_units_Z 1 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 2090 _cell_measurement_theta_min 2.28 _cell_measurement_theta_max 25.34 _exptl_crystal_description plate _exptl_crystal_colour green _exptl_crystal_size_max 0.24 _exptl_crystal_size_mid 0.11 _exptl_crystal_size_min 0.08 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.281 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 294 _exptl_absorpt_coefficient_mu 0.214 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.9504 _exptl_absorpt_correction_T_max 0.9831 _exptl_absorpt_process_details '(SADABS; Sheldrick, 1996)' _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 'Bruker SMART APEX CCD' _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 3888 _diffrn_reflns_av_R_equivalents 0.0130 _diffrn_reflns_av_sigmaI/netI 0.0224 _diffrn_reflns_limit_h_min -5 _diffrn_reflns_limit_h_max 5 _diffrn_reflns_limit_k_min -11 _diffrn_reflns_limit_k_max 10 _diffrn_reflns_limit_l_min -20 _diffrn_reflns_limit_l_max 14 _diffrn_reflns_theta_min 2.28 _diffrn_reflns_theta_max 25.39 _reflns_number_total 2619 _reflns_number_gt 2299 _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^)+(0.0693P)^2^+0.2353P] 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 2619 _refine_ls_number_parameters 182 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0491 _refine_ls_R_factor_gt 0.0435 _refine_ls_wR_factor_ref 0.1227 _refine_ls_wR_factor_gt 0.1173 _refine_ls_goodness_of_fit_ref 1.043 _refine_ls_restrained_S_all 1.043 _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 S1 S 0.54465(10) 0.79649(5) 0.35079(3) 0.04259(19) Uani 1 1 d . . . N1 N 0.1317(7) 1.5358(2) 0.41939(19) 0.1094(11) Uani 1 1 d . . . N2 N 0.7366(6) 1.4528(3) 0.25198(17) 0.0906(8) Uani 1 1 d . . . C1 C 0.7412(4) 0.9224(2) 0.28148(12) 0.0419(4) Uani 1 1 d . . . C2 C 0.6898(4) 1.0656(2) 0.28759(12) 0.0433(4) Uani 1 1 d . . . H2 H 0.7770 1.1480 0.2561 0.052 Uiso 1 1 calc R . . C3 C 0.4863(4) 1.0731(2) 0.34813(11) 0.0388(4) Uani 1 1 d . . . C4 C 0.3468(4) 1.1854(2) 0.38340(11) 0.0387(4) Uani 1 1 d . . . C5 C 0.1551(4) 1.10455(19) 0.44644(11) 0.0362(4) Uani 1 1 d . . . C6 C 0.1819(4) 0.94973(19) 0.44828(11) 0.0352(4) Uani 1 1 d . . . C7 C 0.3890(4) 0.9362(2) 0.38631(11) 0.0374(4) Uani 1 1 d . . . C8 C -0.0284(4) 1.1554(2) 0.49880(11) 0.0370(4) Uani 1 1 d . . . H8 H -0.0469 1.2562 0.4982 0.044 Uiso 1 1 calc R . . C9 C 0.3863(4) 1.3350(2) 0.36182(13) 0.0464(5) Uani 1 1 d . . . C10 C 0.2401(6) 1.4425(2) 0.39650(17) 0.0662(7) Uani 1 1 d . . . C11 C 0.5806(5) 1.3990(2) 0.29998(16) 0.0581(6) Uani 1 1 d . . . C12 C 0.9212(4) 0.8681(2) 0.22113(12) 0.0474(5) Uani 1 1 d . . . H12A H 1.0202 0.7739 0.2491 0.057 Uiso 1 1 calc R . . H12B H 1.0596 0.9403 0.2002 0.057 Uiso 1 1 calc R . . C13 C 0.7549(4) 0.8456(2) 0.14970(13) 0.0493(5) Uani 1 1 d . . . H13A H 0.6194 0.7718 0.1706 0.059 Uiso 1 1 calc R . . H13B H 0.6524 0.9393 0.1226 0.059 Uiso 1 1 calc R . . C14 C 0.9361(5) 0.7940(3) 0.08732(13) 0.0531(5) Uani 1 1 d . . . H14A H 1.0456 0.7030 0.1149 0.064 Uiso 1 1 calc R . . H14B H 1.0654 0.8702 0.0643 0.064 Uiso 1 1 calc R . . C15 C 0.7680(5) 0.7642(3) 0.01818(14) 0.0608(6) Uani 1 1 d . . . H15A H 0.6464 0.6842 0.0412 0.073 Uiso 1 1 calc R . . H15B H 0.6498 0.8536 -0.0069 0.073 Uiso 1 1 calc R . . C16 C 0.9418(5) 0.7215(3) -0.04730(15) 0.0650(6) Uani 1 1 d . . . H16A H 1.0637 0.6337 -0.0222 0.078 Uiso 1 1 calc R . . H16B H 1.0593 0.8027 -0.0717 0.078 Uiso 1 1 calc R . . C17 C 0.7694(7) 0.6881(4) -0.11420(17) 0.0869(9) Uani 1 1 d . . . H17A H 0.6456 0.6112 -0.0903 0.130 Uiso 1 1 calc R . . H17B H 0.8916 0.6545 -0.1517 0.130 Uiso 1 1 calc R . . H17C H 0.6617 0.7774 -0.1430 0.130 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 0.0447(3) 0.0406(3) 0.0474(3) -0.0218(2) 0.0048(2) 0.0025(2) N1 0.156(3) 0.0479(12) 0.131(2) -0.0358(14) 0.080(2) -0.0131(14) N2 0.1016(18) 0.0649(14) 0.108(2) -0.0251(13) 0.0539(16) -0.0202(13) C1 0.0375(9) 0.0500(11) 0.0425(10) -0.0212(9) 0.0012(8) 0.0018(8) C2 0.0426(10) 0.0457(10) 0.0436(11) -0.0156(9) 0.0035(8) -0.0016(8) C3 0.0386(9) 0.0399(10) 0.0403(10) -0.0163(8) 0.0000(7) 0.0024(7) C4 0.0387(9) 0.0394(9) 0.0402(10) -0.0157(8) -0.0011(7) 0.0034(7) C5 0.0384(9) 0.0347(9) 0.0380(9) -0.0153(7) -0.0022(7) 0.0027(7) C6 0.0372(9) 0.0361(9) 0.0353(9) -0.0160(7) -0.0023(7) 0.0038(7) C7 0.0382(9) 0.0392(9) 0.0384(10) -0.0178(8) -0.0016(7) 0.0037(7) C8 0.0396(9) 0.0340(9) 0.0403(10) -0.0166(8) -0.0004(7) 0.0036(7) C9 0.0504(11) 0.0387(10) 0.0527(12) -0.0175(9) 0.0082(9) -0.0008(8) C10 0.0836(17) 0.0372(11) 0.0806(17) -0.0199(11) 0.0332(13) -0.0099(11) C11 0.0654(14) 0.0406(11) 0.0712(15) -0.0198(11) 0.0184(12) -0.0052(10) C12 0.0428(10) 0.0562(12) 0.0484(11) -0.0245(10) 0.0054(8) 0.0027(9) C13 0.0475(11) 0.0567(12) 0.0488(12) -0.0242(10) 0.0043(9) 0.0024(9) C14 0.0541(12) 0.0617(13) 0.0484(12) -0.0241(10) 0.0078(9) -0.0015(10) C15 0.0597(13) 0.0749(15) 0.0557(14) -0.0321(12) 0.0041(10) -0.0003(11) C16 0.0702(15) 0.0768(16) 0.0556(14) -0.0312(12) 0.0104(11) -0.0047(12) C17 0.096(2) 0.116(2) 0.0626(17) -0.0482(17) 0.0008(15) 0.0004(18) _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 C7 1.6973(18) . ? S1 C1 1.741(2) . ? N1 C10 1.134(3) . ? N2 C11 1.138(3) . ? C1 C2 1.365(3) . ? C1 C12 1.500(2) . ? C2 C3 1.424(3) . ? C2 H2 0.9300 . ? C3 C7 1.372(3) . ? C3 C4 1.457(2) . ? C4 C9 1.362(3) . ? C4 C5 1.483(3) . ? C5 C8 1.394(2) . ? C5 C6 1.425(2) . ? C6 C8 1.384(3) 2_576 ? C6 C7 1.465(3) . ? C8 C6 1.384(3) 2_576 ? C8 H8 0.9300 . ? C9 C10 1.430(3) . ? C9 C11 1.431(3) . ? C12 C13 1.521(3) . ? C12 H12A 0.9700 . ? C12 H12B 0.9700 . ? C13 C14 1.518(3) . ? C13 H13A 0.9700 . ? C13 H13B 0.9700 . ? C14 C15 1.521(3) . ? C14 H14A 0.9700 . ? C14 H14B 0.9700 . ? C15 C16 1.504(3) . ? C15 H15A 0.9700 . ? C15 H15B 0.9700 . ? C16 C17 1.516(3) . ? C16 H16A 0.9700 . ? C16 H16B 0.9700 . ? C17 H17A 0.9600 . ? C17 H17B 0.9600 . ? C17 H17C 0.9600 . ? 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 C7 S1 C1 91.65(9) . . ? C2 C1 C12 128.58(19) . . ? C2 C1 S1 111.67(15) . . ? C12 C1 S1 119.59(15) . . ? C1 C2 C3 111.64(18) . . ? C1 C2 H2 124.2 . . ? C3 C2 H2 124.2 . . ? C7 C3 C2 113.12(16) . . ? C7 C3 C4 108.24(17) . . ? C2 C3 C4 138.64(18) . . ? C9 C4 C3 126.18(18) . . ? C9 C4 C5 127.35(17) . . ? C3 C4 C5 106.46(15) . . ? C8 C5 C6 120.58(17) . . ? C8 C5 C4 131.31(16) . . ? C6 C5 C4 108.11(15) . . ? C8 C6 C5 121.90(16) 2_576 . ? C8 C6 C7 131.94(16) 2_576 . ? C5 C6 C7 106.16(16) . . ? C3 C7 C6 111.03(16) . . ? C3 C7 S1 111.91(14) . . ? C6 C7 S1 137.04(15) . . ? C6 C8 C5 117.52(16) 2_576 . ? C6 C8 H8 121.2 2_576 . ? C5 C8 H8 121.2 . . ? C4 C9 C10 124.6(2) . . ? C4 C9 C11 121.79(18) . . ? C10 C9 C11 113.64(18) . . ? N1 C10 C9 174.9(3) . . ? N2 C11 C9 178.1(3) . . ? C1 C12 C13 112.96(16) . . ? C1 C12 H12A 109.0 . . ? C13 C12 H12A 109.0 . . ? C1 C12 H12B 109.0 . . ? C13 C12 H12B 109.0 . . ? H12A C12 H12B 107.8 . . ? C14 C13 C12 113.32(17) . . ? C14 C13 H13A 108.9 . . ? C12 C13 H13A 108.9 . . ? C14 C13 H13B 108.9 . . ? C12 C13 H13B 108.9 . . ? H13A C13 H13B 107.7 . . ? C13 C14 C15 113.17(18) . . ? C13 C14 H14A 108.9 . . ? C15 C14 H14A 108.9 . . ? C13 C14 H14B 108.9 . . ? C15 C14 H14B 108.9 . . ? H14A C14 H14B 107.8 . . ? C16 C15 C14 114.6(2) . . ? C16 C15 H15A 108.6 . . ? C14 C15 H15A 108.6 . . ? C16 C15 H15B 108.6 . . ? C14 C15 H15B 108.6 . . ? H15A C15 H15B 107.6 . . ? C15 C16 C17 113.5(2) . . ? C15 C16 H16A 108.9 . . ? C17 C16 H16A 108.9 . . ? C15 C16 H16B 108.9 . . ? C17 C16 H16B 108.9 . . ? H16A C16 H16B 107.7 . . ? C16 C17 H17A 109.5 . . ? C16 C17 H17B 109.5 . . ? H17A C17 H17B 109.5 . . ? C16 C17 H17C 109.5 . . ? H17A C17 H17C 109.5 . . ? H17B C17 H17C 109.5 . . ? _diffrn_measured_fraction_theta_max 0.981 _diffrn_reflns_theta_full 25.39 _diffrn_measured_fraction_theta_full 0.981 _refine_diff_density_max 0.412 _refine_diff_density_min -0.241 _refine_diff_density_rms 0.046 data_2 _database_code_depnum_ccdc_archive 'CCDC 774475' #TrackingRef '992_web_deposit_cif_file_1_Hongkuntian_1271933456.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C28 H30 O2 S2' _chemical_formula_weight 462.64 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 Triclinic _symmetry_space_group_name_H-M P-1 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 5.1178(10) _cell_length_b 7.8729(13) _cell_length_c 15.815(3) _cell_angle_alpha 85.153(5) _cell_angle_beta 88.003(4) _cell_angle_gamma 76.368(4) _cell_volume 616.98(19) _cell_formula_units_Z 1 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 1209 _cell_measurement_theta_min 2.59 _cell_measurement_theta_max 25.65 _exptl_crystal_description ? _exptl_crystal_colour ? _exptl_crystal_size_max 0.34 _exptl_crystal_size_mid 0.29 _exptl_crystal_size_min 0.11 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.245 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 246 _exptl_absorpt_coefficient_mu 0.238 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.9232 _exptl_absorpt_correction_T_max 0.9738 _exptl_absorpt_process_details '(SADABS; Sheldrick, 1996)' _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 'Bruker APEX 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 3456 _diffrn_reflns_av_R_equivalents 0.0146 _diffrn_reflns_av_sigmaI/netI 0.0322 _diffrn_reflns_limit_h_min -6 _diffrn_reflns_limit_h_max 5 _diffrn_reflns_limit_k_min -7 _diffrn_reflns_limit_k_max 9 _diffrn_reflns_limit_l_min -19 _diffrn_reflns_limit_l_max 19 _diffrn_reflns_theta_min 1.29 _diffrn_reflns_theta_max 25.99 _reflns_number_total 2367 _reflns_number_gt 1875 _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^)+(0.0700P)^2^+0.1114P] 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 2367 _refine_ls_number_parameters 146 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0648 _refine_ls_R_factor_gt 0.0513 _refine_ls_wR_factor_ref 0.1346 _refine_ls_wR_factor_gt 0.1247 _refine_ls_goodness_of_fit_ref 1.057 _refine_ls_restrained_S_all 1.057 _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 C1 C -0.6150(4) 1.4796(3) 0.08315(14) 0.0381(5) Uani 1 1 d . . . H1 H -0.6902 1.4668 0.1370 0.046 Uiso 1 1 calc R . . C2 C -0.3658(4) 1.3762(3) 0.06046(13) 0.0365(5) Uani 1 1 d . . . C3 C -0.2557(4) 1.3978(3) -0.02115(14) 0.0361(5) Uani 1 1 d . . . C4 C 0.0158(4) 1.2689(3) -0.02680(14) 0.0366(5) Uani 1 1 d . . . C5 C 0.0524(4) 1.1728(3) 0.05812(13) 0.0378(5) Uani 1 1 d . . . C6 C -0.1693(4) 1.2366(3) 0.10738(14) 0.0382(5) Uani 1 1 d . . . C7 C 0.2488(4) 1.0403(3) 0.10135(15) 0.0425(5) Uani 1 1 d . . . H7 H 0.4100 0.9835 0.0768 0.051 Uiso 1 1 calc R . . C8 C 0.1740(4) 1.0059(3) 0.18319(15) 0.0449(6) Uani 1 1 d . . . C9 C 0.3227(5) 0.8693(3) 0.24777(17) 0.0551(7) Uani 1 1 d . . . H9A H 0.3750 0.9275 0.2938 0.066 Uiso 1 1 calc R . . H9B H 0.4858 0.8043 0.2215 0.066 Uiso 1 1 calc R . . C10 C 0.1593(5) 0.7406(3) 0.28427(16) 0.0524(6) Uani 1 1 d . . . H10A H 0.0145 0.8017 0.3196 0.063 Uiso 1 1 calc R . . H10B H 0.0792 0.6982 0.2380 0.063 Uiso 1 1 calc R . . C11 C 0.3266(6) 0.5848(4) 0.33672(18) 0.0636(8) Uani 1 1 d . . . H11A H 0.3995 0.6268 0.3846 0.076 Uiso 1 1 calc R . . H11B H 0.4766 0.5272 0.3022 0.076 Uiso 1 1 calc R . . C12 C 0.1669(7) 0.4515(4) 0.3697(2) 0.0754(9) Uani 1 1 d . . . H12A H 0.0179 0.5099 0.4044 0.090 Uiso 1 1 calc R . . H12B H 0.0917 0.4118 0.3217 0.090 Uiso 1 1 calc R . . C13 C 0.3232(8) 0.2955(4) 0.4206(2) 0.0948(12) Uani 1 1 d . . . H13A H 0.4042 0.3347 0.4676 0.114 Uiso 1 1 calc R . . H13B H 0.4675 0.2336 0.3854 0.114 Uiso 1 1 calc R . . C14 C 0.1561(9) 0.1698(5) 0.4552(3) 0.1126(14) Uani 1 1 d . . . H14A H 0.0061 0.2316 0.4873 0.169 Uiso 1 1 calc R . . H14B H 0.2646 0.0778 0.4913 0.169 Uiso 1 1 calc R . . H14C H 0.0914 0.1202 0.4091 0.169 Uiso 1 1 calc R . . O1 O 0.1663(3) 1.2545(2) -0.08805(10) 0.0473(4) Uani 1 1 d . . . S1 S -0.14128(12) 1.13749(8) 0.20758(4) 0.0485(2) 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 0.0325(11) 0.0362(11) 0.0437(12) -0.0030(9) 0.0029(9) -0.0047(9) C2 0.0313(11) 0.0287(10) 0.0475(12) -0.0031(9) -0.0016(9) -0.0031(8) C3 0.0306(11) 0.0304(10) 0.0454(12) -0.0046(9) 0.0012(9) -0.0030(8) C4 0.0316(11) 0.0306(10) 0.0464(12) -0.0065(9) -0.0001(9) -0.0039(9) C5 0.0306(11) 0.0319(11) 0.0490(13) -0.0041(9) -0.0003(9) -0.0031(8) C6 0.0342(11) 0.0326(11) 0.0463(12) -0.0020(9) -0.0010(9) -0.0049(9) C7 0.0293(11) 0.0370(11) 0.0574(14) 0.0002(10) -0.0025(10) -0.0014(9) C8 0.0322(12) 0.0423(12) 0.0563(14) 0.0017(11) -0.0048(10) -0.0019(10) C9 0.0420(14) 0.0562(15) 0.0600(15) 0.0097(12) -0.0080(12) -0.0010(11) C10 0.0496(14) 0.0505(14) 0.0505(14) 0.0050(11) -0.0039(11) -0.0015(12) C11 0.0608(17) 0.0597(17) 0.0622(17) 0.0127(13) -0.0092(14) -0.0026(13) C12 0.075(2) 0.0691(19) 0.077(2) 0.0123(16) -0.0091(16) -0.0123(16) C13 0.089(3) 0.075(2) 0.109(3) 0.028(2) -0.008(2) -0.0075(19) C14 0.122(3) 0.082(3) 0.128(3) 0.030(2) 0.009(3) -0.025(2) O1 0.0369(9) 0.0475(9) 0.0514(10) -0.0036(7) 0.0069(7) 0.0013(7) S1 0.0386(4) 0.0510(4) 0.0479(4) 0.0051(3) 0.0010(2) 0.0019(3) _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 C3 1.384(3) 2_485 ? C1 C2 1.395(3) . ? C1 H1 0.9300 . ? C2 C3 1.403(3) . ? C2 C6 1.471(3) . ? C3 C1 1.384(3) 2_485 ? C3 C4 1.520(3) . ? C4 O1 1.212(2) . ? C4 C5 1.480(3) . ? C5 C6 1.372(3) . ? C5 C7 1.414(3) . ? C6 S1 1.701(2) . ? C7 C8 1.360(3) . ? C7 H7 0.9300 . ? C8 C9 1.504(3) . ? C8 S1 1.750(2) . ? C9 C10 1.525(3) . ? C9 H9A 0.9700 . ? C9 H9B 0.9700 . ? C10 C11 1.519(3) . ? C10 H10A 0.9700 . ? C10 H10B 0.9700 . ? C11 C12 1.524(4) . ? C11 H11A 0.9700 . ? C11 H11B 0.9700 . ? C12 C13 1.487(4) . ? C12 H12A 0.9700 . ? C12 H12B 0.9700 . ? C13 C14 1.512(5) . ? C13 H13A 0.9700 . ? C13 H13B 0.9700 . ? C14 H14A 0.9600 . ? C14 H14B 0.9600 . ? C14 H14C 0.9600 . ? 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 C3 C1 C2 116.36(19) 2_485 . ? C3 C1 H1 121.8 2_485 . ? C2 C1 H1 121.8 . . ? C1 C2 C3 120.92(19) . . ? C1 C2 C6 132.7(2) . . ? C3 C2 C6 106.42(18) . . ? C1 C3 C2 122.72(19) 2_485 . ? C1 C3 C4 128.34(19) 2_485 . ? C2 C3 C4 108.94(18) . . ? O1 C4 C5 129.20(19) . . ? O1 C4 C3 126.09(19) . . ? C5 C4 C3 104.69(17) . . ? C6 C5 C7 113.5(2) . . ? C6 C5 C4 108.29(18) . . ? C7 C5 C4 138.2(2) . . ? C5 C6 C2 111.66(19) . . ? C5 C6 S1 111.68(16) . . ? C2 C6 S1 136.63(17) . . ? C8 C7 C5 112.0(2) . . ? C8 C7 H7 124.0 . . ? C5 C7 H7 124.0 . . ? C7 C8 C9 127.7(2) . . ? C7 C8 S1 111.50(16) . . ? C9 C8 S1 120.78(18) . . ? C8 C9 C10 113.6(2) . . ? C8 C9 H9A 108.8 . . ? C10 C9 H9A 108.8 . . ? C8 C9 H9B 108.8 . . ? C10 C9 H9B 108.8 . . ? H9A C9 H9B 107.7 . . ? C11 C10 C9 113.0(2) . . ? C11 C10 H10A 109.0 . . ? C9 C10 H10A 109.0 . . ? C11 C10 H10B 109.0 . . ? C9 C10 H10B 109.0 . . ? H10A C10 H10B 107.8 . . ? C10 C11 C12 113.1(2) . . ? C10 C11 H11A 109.0 . . ? C12 C11 H11A 109.0 . . ? C10 C11 H11B 109.0 . . ? C12 C11 H11B 109.0 . . ? H11A C11 H11B 107.8 . . ? C13 C12 C11 115.1(3) . . ? C13 C12 H12A 108.5 . . ? C11 C12 H12A 108.5 . . ? C13 C12 H12B 108.5 . . ? C11 C12 H12B 108.5 . . ? H12A C12 H12B 107.5 . . ? C12 C13 C14 113.6(3) . . ? C12 C13 H13A 108.8 . . ? C14 C13 H13A 108.8 . . ? C12 C13 H13B 108.8 . . ? C14 C13 H13B 108.8 . . ? H13A C13 H13B 107.7 . . ? C13 C14 H14A 109.5 . . ? C13 C14 H14B 109.5 . . ? H14A C14 H14B 109.5 . . ? C13 C14 H14C 109.5 . . ? H14A C14 H14C 109.5 . . ? H14B C14 H14C 109.5 . . ? C6 S1 C8 91.37(11) . . ? _diffrn_measured_fraction_theta_max 0.975 _diffrn_reflns_theta_full 25.99 _diffrn_measured_fraction_theta_full 0.975 _refine_diff_density_max 0.401 _refine_diff_density_min -0.176 _refine_diff_density_rms 0.051