# Electronic Supplementary Material (ESI) for Organic & Biomolecular Chemistry # This journal is © The Royal Society of Chemistry 2013 ####################################################################### # # Cambridge Crystallographic Data Centre # CCDC # ####################################################################### # # This CIF contains data from an original supplementary publication # deposited with the CCDC, and may include chemical, crystal, # experimental, refinement, atomic coordinates, # anisotropic displacement parameters and molecular geometry data, # as required by the journal to which it was submitted. # # This CIF is provided on the understanding that it is used for bona # fide research purposes only. It may contain copyright material # of the CCDC or of third parties, and may not be copied or further # disseminated in any form, whether machine-readable or not, # except for the purpose of generating routine backup copies # on your local computer system. # # For further information on the CCDC, data deposition and # data retrieval see: # www.ccdc.cam.ac.uk # # Bona fide researchers may freely download Mercury and enCIFer # from this site to visualise CIF-encoded structures and # to carry out CIF format checking respectively. # ####################################################################### data_1b _database_code_depnum_ccdc_archive 'CCDC 921750' #TrackingRef 'JOC 01-13.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C26 H28 O2 S4' _chemical_formula_sum 'C26 H28 O2 S4' _chemical_formula_weight 500.72 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' 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' _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 5.7198(15) _cell_length_b 9.0209(19) _cell_length_c 11.863(3) _cell_angle_alpha 79.850(19) _cell_angle_beta 78.78(2) _cell_angle_gamma 87.139(19) _cell_volume 590.9(3) _cell_formula_units_Z 1 _cell_measurement_temperature 173 _cell_measurement_reflns_used 1502 _cell_measurement_theta_min 3.8518 _cell_measurement_theta_max 72.7013 _exptl_crystal_description plates _exptl_crystal_colour 'Lusterous bronze' _exptl_crystal_size_max 0.30 _exptl_crystal_size_mid 0.22 _exptl_crystal_size_min 0.06 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.407 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 264 _exptl_absorpt_coefficient_mu 3.866 _exptl_absorpt_correction_type analytical _exptl_absorpt_correction_T_min 0.454 _exptl_absorpt_correction_T_max 0.799 _exptl_absorpt_process_details ; CrysAlisPro, Agilent Technologies, Version 1.171.35.11 (release 16-05-2011 CrysAlis171 .NET) (compiled May 16 2011,17:55:39) Analytical numeric absorption correction using a multifaceted crystal model based on expressions derived by R.C. Clark & J.S. Reid. (Clark, R. C. & Reid, J. S. (1995). Acta Cryst. A51, 887-897) ; _exptl_special_details ; ? ; _diffrn_ambient_temperature 173 _diffrn_radiation_wavelength 1.54184 _diffrn_radiation_type CuK\a _diffrn_radiation_source 'Enhance Ultra (Cu) X-ray Source' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'OD Xcalibur PX Ultra' _diffrn_measurement_method 'omega scans' _diffrn_detector_area_resol_mean 8.2556 _diffrn_standards_number 0 _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 3835 _diffrn_reflns_av_R_equivalents 0.0500 _diffrn_reflns_av_sigmaI/netI 0.0426 _diffrn_reflns_limit_h_min -6 _diffrn_reflns_limit_h_max 6 _diffrn_reflns_limit_k_min -8 _diffrn_reflns_limit_k_max 11 _diffrn_reflns_limit_l_min -14 _diffrn_reflns_limit_l_max 14 _diffrn_reflns_theta_min 3.86 _diffrn_reflns_theta_max 72.85 _reflns_number_total 2253 _reflns_number_gt 1864 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'CrysAlis CCD, Oxford Diffraction Ltd' _computing_cell_refinement 'CrysAlis RED, Oxford Diffraction Ltd' _computing_data_reduction 'CrysAlis RED, Oxford Diffraction Ltd' _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^)+(0.1555P)^2^+0.0000P] 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 2253 _refine_ls_number_parameters 145 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0775 _refine_ls_R_factor_gt 0.0689 _refine_ls_wR_factor_ref 0.2082 _refine_ls_wR_factor_gt 0.1966 _refine_ls_goodness_of_fit_ref 1.074 _refine_ls_restrained_S_all 1.074 _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 0.82839(13) 0.68304(9) 0.51882(7) 0.0418(3) Uani 1 1 d . . . C2 C 0.7835(5) 0.8769(4) 0.4610(3) 0.0404(7) Uani 1 1 d . . . O2 O 0.9361(4) 0.9484(3) 0.3900(2) 0.0481(6) Uani 1 1 d . . . C3 C 0.5383(5) 0.9252(3) 0.5130(3) 0.0374(7) Uani 1 1 d . . . C4 C 0.4093(5) 0.8034(4) 0.5860(3) 0.0392(7) Uani 1 1 d . . . H4A H 0.2489 0.8139 0.6244 0.047 Uiso 1 1 calc R . . C5 C 0.5324(5) 0.6697(4) 0.5970(3) 0.0378(7) Uani 1 1 d . . . C6 C 0.4550(5) 0.5272(4) 0.6624(3) 0.0381(7) Uani 1 1 d . . . S7 S 0.17070(13) 0.50438(8) 0.74702(7) 0.0402(3) Uani 1 1 d . . . C8 C 0.2217(6) 0.3157(4) 0.7910(3) 0.0403(7) Uani 1 1 d . . . C9 C 0.4453(6) 0.2733(4) 0.7421(3) 0.0425(7) Uani 1 1 d . . . H9A H 0.5050 0.1729 0.7557 0.051 Uiso 1 1 calc R . . C10 C 0.5782(5) 0.3913(4) 0.6700(3) 0.0412(7) Uani 1 1 d . . . H10A H 0.7372 0.3793 0.6303 0.049 Uiso 1 1 calc R . . C11 C 0.0286(6) 0.2193(4) 0.8690(3) 0.0432(7) Uani 1 1 d . . . H11A H 0.1033 0.1407 0.9207 0.052 Uiso 1 1 calc R . . H11B H -0.0505 0.1677 0.8199 0.052 Uiso 1 1 calc R . . C12 C -0.1631(5) 0.3027(4) 0.9453(3) 0.0424(7) Uani 1 1 d . . . H12A H -0.0856 0.3574 0.9931 0.051 Uiso 1 1 calc R . . H12B H -0.2453 0.3779 0.8944 0.051 Uiso 1 1 calc R . . C13 C -0.3464(6) 0.1961(4) 1.0255(3) 0.0455(7) Uani 1 1 d . . . H13A H -0.2685 0.1320 1.0847 0.055 Uiso 1 1 calc R . . H13B H -0.4032 0.1292 0.9790 0.055 Uiso 1 1 calc R . . C14 C -0.5605(6) 0.2773(4) 1.0874(3) 0.0459(8) Uani 1 1 d . . . H14A H -0.5035 0.3469 1.1317 0.055 Uiso 1 1 calc R . . H14B H -0.6422 0.3385 1.0283 0.055 Uiso 1 1 calc R . . C15 C -0.7371(6) 0.1708(4) 1.1699(3) 0.0526(9) Uani 1 1 d . . . H15A H -0.8690 0.2288 1.2082 0.079 Uiso 1 1 calc R . . H15B H -0.6576 0.1102 1.2290 0.079 Uiso 1 1 calc R . . H15C H -0.7992 0.1042 1.1261 0.079 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 0.0348(5) 0.0410(5) 0.0481(5) -0.0141(3) 0.0014(3) 0.0002(3) C2 0.0375(16) 0.0427(16) 0.0433(16) -0.0181(13) -0.0035(12) -0.0013(12) O2 0.0413(12) 0.0420(13) 0.0557(13) -0.0120(10) 0.0074(10) -0.0018(9) C3 0.0352(15) 0.0369(15) 0.0414(15) -0.0152(12) -0.0028(12) -0.0018(11) C4 0.0362(15) 0.0395(16) 0.0432(16) -0.0170(13) -0.0013(12) -0.0020(12) C5 0.0312(14) 0.0460(17) 0.0382(14) -0.0186(13) -0.0006(11) -0.0025(12) C6 0.0361(15) 0.0380(16) 0.0416(15) -0.0168(12) -0.0017(11) -0.0013(11) S7 0.0356(5) 0.0361(5) 0.0477(5) -0.0142(3) 0.0013(3) -0.0001(3) C8 0.0367(15) 0.0435(17) 0.0425(16) -0.0162(13) -0.0040(12) 0.0003(12) C9 0.0414(17) 0.0378(16) 0.0482(17) -0.0109(13) -0.0057(13) 0.0032(12) C10 0.0342(15) 0.0450(17) 0.0462(16) -0.0189(14) -0.0031(12) 0.0032(12) C11 0.0446(17) 0.0367(15) 0.0454(17) -0.0107(13) 0.0023(13) -0.0036(13) C12 0.0403(16) 0.0378(16) 0.0486(17) -0.0136(13) -0.0009(13) -0.0032(12) C13 0.0456(17) 0.0397(17) 0.0499(17) -0.0122(13) -0.0014(13) -0.0009(13) C14 0.0436(17) 0.0430(17) 0.0515(18) -0.0177(14) -0.0011(13) -0.0017(13) C15 0.0472(18) 0.052(2) 0.058(2) -0.0200(16) 0.0020(15) -0.0006(15) _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 C5 1.764(3) . ? S1 C2 1.788(3) . ? C2 O2 1.210(4) . ? C2 C3 1.495(4) . ? C3 C3 1.399(6) 2_676 ? C3 C4 1.413(4) . ? C4 C5 1.365(4) . ? C5 C6 1.422(5) . ? C6 C10 1.382(4) . ? C6 S7 1.738(3) . ? S7 C8 1.718(3) . ? C8 C9 1.364(4) . ? C8 C11 1.499(4) . ? C9 C10 1.395(5) . ? C11 C12 1.535(4) . ? C12 C13 1.523(4) . ? C13 C14 1.525(4) . ? C14 C15 1.511(5) . ? 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 C5 S1 C2 91.42(15) . . ? O2 C2 C3 129.4(3) . . ? O2 C2 S1 121.7(2) . . ? C3 C2 S1 108.9(2) . . ? C3 C3 C4 128.0(3) 2_676 . ? C3 C3 C2 120.5(3) 2_676 . ? C4 C3 C2 111.5(3) . . ? C5 C4 C3 115.0(3) . . ? C4 C5 C6 129.0(3) . . ? C4 C5 S1 113.1(2) . . ? C6 C5 S1 117.9(2) . . ? C10 C6 C5 128.7(3) . . ? C10 C6 S7 110.0(2) . . ? C5 C6 S7 121.3(3) . . ? C8 S7 C6 92.06(15) . . ? C9 C8 C11 128.5(3) . . ? C9 C8 S7 111.1(3) . . ? C11 C8 S7 120.4(2) . . ? C8 C9 C10 113.7(3) . . ? C6 C10 C9 113.1(3) . . ? C8 C11 C12 115.6(3) . . ? C13 C12 C11 112.3(3) . . ? C12 C13 C14 113.3(3) . . ? C15 C14 C13 112.9(3) . . ? _diffrn_measured_fraction_theta_max 0.956 _diffrn_reflns_theta_full 71.00 _diffrn_measured_fraction_theta_full 0.982 _refine_diff_density_max 0.554 _refine_diff_density_min -0.625 _refine_diff_density_rms 0.106 data_1c _database_code_depnum_ccdc_archive 'CCDC 921751' #TrackingRef 'JOC 01-13.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C24 H24 O2 S6' _chemical_formula_sum 'C24 H24 O2 S6' _chemical_formula_weight 536.79 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' 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' _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 6.3559(4) _cell_length_b 8.6356(3) _cell_length_c 11.6399(6) _cell_angle_alpha 78.832(4) _cell_angle_beta 77.408(5) _cell_angle_gamma 87.543(4) _cell_volume 611.71(6) _cell_formula_units_Z 1 _cell_measurement_temperature 173 _cell_measurement_reflns_used 3199 _cell_measurement_theta_min 3.9595 _cell_measurement_theta_max 72.1840 _exptl_crystal_description 'platy needles' _exptl_crystal_colour 'Dark bronze' _exptl_crystal_size_max 0.34 _exptl_crystal_size_mid 0.30 _exptl_crystal_size_min 0.04 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.457 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 280 _exptl_absorpt_coefficient_mu 5.330 _exptl_absorpt_correction_type analytical _exptl_absorpt_correction_T_min 0.289 _exptl_absorpt_correction_T_max 0.796 _exptl_absorpt_process_details ; CrysAlisPro, Agilent Technologies, Version 1.171.35.21 (release 20-01-2012 CrysAlis171 .NET) (compiled Jan 23 2012,18:06:46) Analytical numeric absorption correction using a multifaceted crystal model based on expressions derived by R.C. Clark & J.S. Reid. (Clark, R. C. & Reid, J. S. (1995). Acta Cryst. A51, 887-897) ; _exptl_special_details ; ? ; _diffrn_ambient_temperature 173 _diffrn_radiation_wavelength 1.54184 _diffrn_radiation_type CuK\a _diffrn_radiation_source 'Enhance Ultra (Cu) X-ray Source' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'OD Xcalibur PX Ultra' _diffrn_measurement_method 'omega scans' _diffrn_detector_area_resol_mean 8.2556 _diffrn_standards_number 0 _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 4464 _diffrn_reflns_av_R_equivalents 0.0215 _diffrn_reflns_av_sigmaI/netI 0.0261 _diffrn_reflns_limit_h_min -7 _diffrn_reflns_limit_h_max 7 _diffrn_reflns_limit_k_min -10 _diffrn_reflns_limit_k_max 7 _diffrn_reflns_limit_l_min -14 _diffrn_reflns_limit_l_max 14 _diffrn_reflns_theta_min 3.96 _diffrn_reflns_theta_max 72.33 _reflns_number_total 2354 _reflns_number_gt 2103 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'CrysAlis CCD, Oxford Diffraction Ltd' _computing_cell_refinement 'CrysAlis RED, Oxford Diffraction Ltd' _computing_data_reduction 'CrysAlis RED, Oxford Diffraction Ltd' _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^)+(0.0439P)^2^+0.1345P] 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 0.0083(12) _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_number_reflns 2354 _refine_ls_number_parameters 146 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0349 _refine_ls_R_factor_gt 0.0306 _refine_ls_wR_factor_ref 0.0801 _refine_ls_wR_factor_gt 0.0779 _refine_ls_goodness_of_fit_ref 1.056 _refine_ls_restrained_S_all 1.056 _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_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group S1 S 0.33386(7) 0.19116(5) 0.51155(4) 0.03476(15) Uani 1 1 d . . . C2 C 0.0805(3) 0.2842(2) 0.55802(16) 0.0297(4) Uani 1 1 d . . . O2 O -0.0649(2) 0.21484(15) 0.63303(13) 0.0400(3) Uani 1 1 d . . . C3 C 0.0876(3) 0.45049(19) 0.49073(15) 0.0261(4) Uani 1 1 d . . . C4 C 0.2908(3) 0.4855(2) 0.41098(15) 0.0268(4) Uani 1 1 d . . . H4A H 0.3236 0.5862 0.3614 0.032 Uiso 1 1 calc R . . C5 C 0.4348(3) 0.36422(19) 0.41086(14) 0.0260(4) Uani 1 1 d . . . C6 C 0.6512(3) 0.36076(19) 0.34186(15) 0.0258(4) Uani 1 1 d . . . S7 S 0.76316(7) 0.52375(5) 0.23730(4) 0.02761(14) Uani 1 1 d . . . C8 C 1.0051(3) 0.4266(2) 0.20284(15) 0.0273(4) Uani 1 1 d . . . C9 C 0.9978(3) 0.2759(2) 0.26848(16) 0.0306(4) Uani 1 1 d . . . H9A H 1.1157 0.2043 0.2614 0.037 Uiso 1 1 calc R . . C10 C 0.7977(3) 0.2385(2) 0.34727(16) 0.0298(4) Uani 1 1 d . . . H10A H 0.7666 0.1390 0.3990 0.036 Uiso 1 1 calc R . . S11 S 1.22796(7) 0.50888(5) 0.09748(4) 0.03441(15) Uani 1 1 d . . . C12 C 1.1475(3) 0.7107(2) 0.04990(17) 0.0331(4) Uani 1 1 d . . . H12A H 1.0163 0.7129 0.0168 0.040 Uiso 1 1 calc R . . H12B H 1.1159 0.7661 0.1187 0.040 Uiso 1 1 calc R . . C13 C 1.3344(3) 0.7907(2) -0.04597(16) 0.0311(4) Uani 1 1 d . . . H13A H 1.4635 0.7875 -0.0109 0.037 Uiso 1 1 calc R . . H13B H 1.3678 0.7306 -0.1120 0.037 Uiso 1 1 calc R . . C14 C 1.2875(3) 0.9616(2) -0.09710(18) 0.0368(4) Uani 1 1 d . . . H14A H 1.2538 1.0225 -0.0315 0.044 Uiso 1 1 calc R . . H14B H 1.1599 0.9656 -0.1335 0.044 Uiso 1 1 calc R . . C15 C 1.4798(4) 1.0368(2) -0.19177(19) 0.0434(5) Uani 1 1 d . . . H15A H 1.4451 1.1464 -0.2232 0.065 Uiso 1 1 calc R . . H15B H 1.5122 0.9776 -0.2573 0.065 Uiso 1 1 calc R . . H15C H 1.6056 1.0348 -0.1555 0.065 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 0.0312(3) 0.0282(2) 0.0359(3) 0.00419(18) 0.00294(19) -0.00065(18) C2 0.0292(9) 0.0285(9) 0.0277(9) -0.0017(7) -0.0007(7) -0.0028(7) O2 0.0352(7) 0.0320(7) 0.0416(8) 0.0051(6) 0.0056(6) -0.0030(5) C3 0.0262(8) 0.0269(8) 0.0234(8) -0.0022(7) -0.0029(7) -0.0047(6) C4 0.0257(9) 0.0288(9) 0.0241(8) -0.0035(7) -0.0019(7) -0.0047(7) C5 0.0262(9) 0.0278(8) 0.0226(8) -0.0030(7) -0.0027(7) -0.0045(7) C6 0.0261(8) 0.0256(8) 0.0242(8) -0.0031(6) -0.0033(7) -0.0028(6) S7 0.0247(2) 0.0261(2) 0.0273(2) -0.00094(16) 0.00095(16) 0.00004(16) C8 0.0242(8) 0.0304(9) 0.0263(8) -0.0064(7) -0.0026(7) -0.0007(7) C9 0.0286(9) 0.0287(9) 0.0333(9) -0.0050(7) -0.0053(7) 0.0019(7) C10 0.0311(9) 0.0274(9) 0.0292(9) -0.0025(7) -0.0047(7) -0.0028(7) S11 0.0262(2) 0.0335(3) 0.0354(3) 0.00055(18) 0.00425(18) 0.00090(17) C12 0.0310(9) 0.0304(9) 0.0345(10) -0.0040(8) -0.0013(8) -0.0016(7) C13 0.0290(9) 0.0300(9) 0.0312(9) -0.0049(7) 0.0003(7) -0.0026(7) C14 0.0381(10) 0.0321(10) 0.0371(10) -0.0038(8) -0.0039(8) 0.0004(8) C15 0.0530(13) 0.0332(10) 0.0378(11) 0.0022(8) -0.0034(10) -0.0051(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 S1 C5 1.7592(17) . ? S1 C2 1.7914(18) . ? C2 O2 1.212(2) . ? C2 C3 1.494(2) . ? C3 C3 1.380(3) 2_566 ? C3 C4 1.422(2) . ? C4 C5 1.361(2) . ? C5 C6 1.436(2) . ? C6 C10 1.379(2) . ? C6 S7 1.7359(17) . ? S7 C8 1.7264(17) . ? C8 C9 1.373(2) . ? C8 S11 1.7337(18) . ? C9 C10 1.405(2) . ? S11 C12 1.8111(18) . ? C12 C13 1.525(2) . ? C13 C14 1.523(3) . ? C14 C15 1.528(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 C5 S1 C2 91.56(8) . . ? O2 C2 C3 129.19(17) . . ? O2 C2 S1 121.86(14) . . ? C3 C2 S1 108.95(12) . . ? C3 C3 C4 127.8(2) 2_566 . ? C3 C3 C2 121.09(19) 2_566 . ? C4 C3 C2 111.12(15) . . ? C5 C4 C3 115.19(15) . . ? C4 C5 C6 129.04(16) . . ? C4 C5 S1 113.19(13) . . ? C6 C5 S1 117.77(13) . . ? C10 C6 C5 127.97(16) . . ? C10 C6 S7 110.73(13) . . ? C5 C6 S7 121.29(13) . . ? C8 S7 C6 91.67(8) . . ? C9 C8 S7 111.46(13) . . ? C9 C8 S11 124.41(14) . . ? S7 C8 S11 124.13(10) . . ? C8 C9 C10 112.92(16) . . ? C6 C10 C9 113.22(16) . . ? C8 S11 C12 103.98(8) . . ? C13 C12 S11 107.23(12) . . ? C14 C13 C12 113.22(15) . . ? C13 C14 C15 111.24(16) . . ? _diffrn_measured_fraction_theta_max 0.972 _diffrn_reflns_theta_full 71.50 _diffrn_measured_fraction_theta_full 0.982 _refine_diff_density_max 0.252 _refine_diff_density_min -0.239 _refine_diff_density_rms 0.048 #===END