# Electronic Supplementary Material (ESI) for Organic & Biomolecular Chemistry # This journal is © The Royal Society of Chemistry 2012 data_global _journal_name_full Org.Biomol.Chem. _journal_coden_cambridge 0177 _journal_year ? _journal_volume ? _journal_page_first ? _publ_contact_author_name 'Louise Male' _publ_contact_author_email l.male@bham.ac.uk loop_ _publ_author_name B.Defaut T.B.Parsons N.Spencer L.Male B.M.Kariuki R.S.Grainger data_6 _database_code_depnum_ccdc_archive 'CCDC 855564' #TrackingRef '- Hydrindanes.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C12 H18 O3' _chemical_formula_sum 'C12 H18 O3' _chemical_formula_weight 210.26 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' _symmetry_cell_setting Monoclinic _symmetry_space_group_name_H-M P21/n loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, y+1/2, -z+1/2' '-x, -y, -z' 'x-1/2, -y-1/2, z-1/2' _cell_length_a 7.106(3) _cell_length_b 14.861(3) _cell_length_c 11.691(3) _cell_angle_alpha 90.00 _cell_angle_beta 101.499(16) _cell_angle_gamma 90.00 _cell_volume 1209.8(6) _cell_formula_units_Z 4 _cell_measurement_temperature 296(2) _cell_measurement_reflns_used 1179 _cell_measurement_theta_min 4.87 _cell_measurement_theta_max 62.70 _exptl_crystal_description block _exptl_crystal_colour colourless _exptl_crystal_size_max 0.34 _exptl_crystal_size_mid 0.30 _exptl_crystal_size_min 0.20 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.154 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 456 _exptl_absorpt_coefficient_mu 0.662 _exptl_absorpt_correction_type empirical _exptl_absorpt_correction_T_min 0.8062 _exptl_absorpt_correction_T_max 0.8790 _exptl_absorpt_process_details Sadabs _exptl_special_details ; ? ; _diffrn_ambient_temperature 296(2) _diffrn_radiation_wavelength 1.54178 _diffrn_radiation_type CuK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Bruker Smart 6000 CCD' _diffrn_measurement_method 'CCD scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 5705 _diffrn_reflns_av_R_equivalents 0.0428 _diffrn_reflns_av_sigmaI/netI 0.2770 _diffrn_reflns_limit_h_min -8 _diffrn_reflns_limit_h_max 8 _diffrn_reflns_limit_k_min -15 _diffrn_reflns_limit_k_max 17 _diffrn_reflns_limit_l_min -12 _diffrn_reflns_limit_l_max 12 _diffrn_reflns_theta_min 4.87 _diffrn_reflns_theta_max 62.70 _reflns_number_total 1922 _reflns_number_gt 1179 _reflns_threshold_expression >2\s(I) _computing_data_collection SMART _computing_cell_refinement SAINTPLUS _computing_data_reduction SAINTPLUS _computing_structure_solution SHELXTL _computing_structure_refinement 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^ > 2\s(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^)+(0.0608P)^2^+0.1624P] 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 1922 _refine_ls_number_parameters 137 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0735 _refine_ls_R_factor_gt 0.0497 _refine_ls_wR_factor_ref 0.1473 _refine_ls_wR_factor_gt 0.1273 _refine_ls_goodness_of_fit_ref 1.068 _refine_ls_restrained_S_all 1.068 _refine_ls_shift/su_max 0.007 _refine_ls_shift/su_mean 0.001 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 1.2110(4) 0.45619(19) 0.8975(2) 0.0747(8) Uani 1 1 d . . . H1A H 1.3231 0.4327 0.9503 0.090 Uiso 1 1 calc R . . H1B H 1.1218 0.4798 0.9430 0.090 Uiso 1 1 calc R . . C2 C 1.2686(4) 0.52997(16) 0.8170(2) 0.0665(7) Uani 1 1 d . . . H2A H 1.2309 0.5890 0.8400 0.080 Uiso 1 1 calc R . . H2B H 1.4064 0.5297 0.8215 0.080 Uiso 1 1 calc R . . C3 C 1.0425(3) 0.43172(15) 0.7063(2) 0.0577(7) Uani 1 1 d . . . C4 C 1.0488(4) 0.36588(19) 0.6045(2) 0.0699(7) Uani 1 1 d . . . H4A H 1.1793 0.3447 0.6093 0.084 Uiso 1 1 calc R . . H4B H 1.0092 0.3970 0.5307 0.084 Uiso 1 1 calc R . . C5 C 0.9133(3) 0.28383(16) 0.6095(2) 0.0627(7) Uani 1 1 d . . . H5A H 0.9223 0.2429 0.5462 0.075 Uiso 1 1 calc R . . H5B H 0.9563 0.2519 0.6823 0.075 Uiso 1 1 calc R . . C6 C 0.6994(3) 0.31209(14) 0.59998(18) 0.0478(6) Uani 1 1 d . . . C7 C 0.5813(4) 0.23183(16) 0.6416(2) 0.0609(7) Uani 1 1 d . . . H7A H 0.4462 0.2370 0.6063 0.073 Uiso 1 1 calc R . . H7B H 0.6281 0.1744 0.6194 0.073 Uiso 1 1 calc R . . C8 C 0.6108(4) 0.23887(18) 0.7781(2) 0.0746(8) Uani 1 1 d . . . H8A H 0.4928 0.2244 0.8039 0.089 Uiso 1 1 calc R . . H8B H 0.7108 0.1980 0.8154 0.089 Uiso 1 1 calc R . . C9 C 0.6699(3) 0.33804(17) 0.8079(2) 0.0595(6) Uani 1 1 d . . . C10 C 0.6835(3) 0.38881(14) 0.69246(18) 0.0490(6) Uani 1 1 d . . . H10 H 0.5581 0.4173 0.6656 0.059 Uiso 1 1 calc R . . C11 C 0.8350(3) 0.46609(14) 0.7033(2) 0.0594(7) Uani 1 1 d . . . H11A H 0.7987 0.5068 0.6377 0.071 Uiso 1 1 calc R . . H11B H 0.8333 0.4999 0.7741 0.071 Uiso 1 1 calc R . . C12 C 0.6115(4) 0.3413(2) 0.4713(2) 0.0757(8) Uani 1 1 d . . . H12A H 0.6882 0.3885 0.4481 0.114 Uiso 1 1 calc R . . H12B H 0.4827 0.3626 0.4671 0.114 Uiso 1 1 calc R . . H12C H 0.6099 0.2907 0.4201 0.114 Uiso 1 1 calc R . . O1 O 1.1200(2) 0.38653(11) 0.81660(14) 0.0683(5) Uani 1 1 d . . . O2 O 1.1685(3) 0.50855(14) 0.69977(15) 0.0871(7) Uani 1 1 d . . . O3 O 0.6973(3) 0.37183(15) 0.90767(15) 0.0910(7) 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 0.0747(19) 0.0881(19) 0.0585(16) -0.0059(14) 0.0067(13) -0.0105(15) C2 0.0659(16) 0.0593(14) 0.0716(17) -0.0129(12) 0.0069(12) -0.0072(12) C3 0.0599(15) 0.0579(14) 0.0521(14) 0.0091(11) 0.0039(11) -0.0155(12) C4 0.0526(15) 0.0904(18) 0.0696(17) -0.0082(14) 0.0193(12) -0.0048(13) C5 0.0632(16) 0.0611(15) 0.0654(16) -0.0179(12) 0.0167(12) 0.0031(12) C6 0.0533(13) 0.0452(11) 0.0442(13) -0.0041(9) 0.0077(9) -0.0046(10) C7 0.0650(16) 0.0525(13) 0.0634(16) -0.0025(11) 0.0085(11) -0.0094(11) C8 0.087(2) 0.0713(16) 0.0640(18) 0.0104(13) 0.0129(13) -0.0207(14) C9 0.0568(15) 0.0743(16) 0.0478(15) -0.0061(12) 0.0116(10) -0.0020(12) C10 0.0483(13) 0.0444(11) 0.0530(14) -0.0038(9) 0.0071(9) 0.0051(9) C11 0.0685(17) 0.0417(12) 0.0648(16) -0.0007(11) 0.0053(12) -0.0027(11) C12 0.0852(19) 0.0876(19) 0.0488(15) 0.0006(13) 0.0002(12) -0.0198(15) O1 0.0675(11) 0.0655(10) 0.0653(11) 0.0124(8) -0.0028(8) -0.0114(8) O2 0.0893(13) 0.0967(13) 0.0682(12) 0.0169(10) -0.0012(10) -0.0522(11) O3 0.1046(16) 0.1170(16) 0.0541(12) -0.0212(11) 0.0223(10) -0.0195(13) _geom_special_details ; All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell s.u.'s are taken into account individually in the estimation of s.u.'s in distances, angles and torsion angles; correlations between s.u.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell s.u.'s is used for estimating s.u.'s 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 O1 1.463(3) . ? C1 C2 1.552(4) . ? C1 H1A 0.9700 . ? C1 H1B 0.9700 . ? C2 O2 1.448(3) . ? C2 H2A 0.9700 . ? C2 H2B 0.9700 . ? C3 O1 1.461(3) . ? C3 O2 1.462(3) . ? C3 C4 1.548(4) . ? C3 C11 1.554(3) . ? C4 C5 1.562(3) . ? C4 H4A 0.9700 . ? C4 H4B 0.9700 . ? C5 C6 1.559(3) . ? C5 H5A 0.9700 . ? C5 H5B 0.9700 . ? C6 C12 1.571(3) . ? C6 C7 1.590(3) . ? C6 C10 1.591(3) . ? C7 C8 1.570(3) . ? C7 H7A 0.9700 . ? C7 H7B 0.9700 . ? C8 C9 1.553(4) . ? C8 H8A 0.9700 . ? C8 H8B 0.9700 . ? C9 O3 1.249(3) . ? C9 C10 1.566(3) . ? C10 C11 1.562(3) . ? C10 H10 0.9800 . ? C11 H11A 0.9700 . ? C11 H11B 0.9700 . ? C12 H12A 0.9600 . ? C12 H12B 0.9600 . ? C12 H12C 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 O1 C1 C2 104.09(19) . . ? O1 C1 H1A 110.9 . . ? C2 C1 H1A 110.9 . . ? O1 C1 H1B 110.9 . . ? C2 C1 H1B 110.9 . . ? H1A C1 H1B 109.0 . . ? O2 C2 C1 106.24(19) . . ? O2 C2 H2A 110.5 . . ? C1 C2 H2A 110.5 . . ? O2 C2 H2B 110.5 . . ? C1 C2 H2B 110.5 . . ? H2A C2 H2B 108.7 . . ? O1 C3 O2 106.13(16) . . ? O1 C3 C4 108.9(2) . . ? O2 C3 C4 110.0(2) . . ? O1 C3 C11 111.08(19) . . ? O2 C3 C11 109.27(19) . . ? C4 C3 C11 111.29(18) . . ? C3 C4 C5 110.66(19) . . ? C3 C4 H4A 109.5 . . ? C5 C4 H4A 109.5 . . ? C3 C4 H4B 109.5 . . ? C5 C4 H4B 109.5 . . ? H4A C4 H4B 108.1 . . ? C6 C5 C4 112.73(19) . . ? C6 C5 H5A 109.0 . . ? C4 C5 H5A 109.0 . . ? C6 C5 H5B 109.0 . . ? C4 C5 H5B 109.0 . . ? H5A C5 H5B 107.8 . . ? C5 C6 C12 109.8(2) . . ? C5 C6 C7 110.04(18) . . ? C12 C6 C7 111.56(17) . . ? C5 C6 C10 110.18(17) . . ? C12 C6 C10 112.60(18) . . ? C7 C6 C10 102.49(17) . . ? C8 C7 C6 106.83(17) . . ? C8 C7 H7A 110.4 . . ? C6 C7 H7A 110.4 . . ? C8 C7 H7B 110.4 . . ? C6 C7 H7B 110.4 . . ? H7A C7 H7B 108.6 . . ? C9 C8 C7 105.46(19) . . ? C9 C8 H8A 110.6 . . ? C7 C8 H8A 110.6 . . ? C9 C8 H8B 110.6 . . ? C7 C8 H8B 110.6 . . ? H8A C8 H8B 108.8 . . ? O3 C9 C8 125.2(2) . . ? O3 C9 C10 125.9(2) . . ? C8 C9 C10 108.92(18) . . ? C11 C10 C9 116.39(18) . . ? C11 C10 C6 116.17(19) . . ? C9 C10 C6 105.39(17) . . ? C11 C10 H10 106.0 . . ? C9 C10 H10 106.0 . . ? C6 C10 H10 106.0 . . ? C3 C11 C10 113.30(18) . . ? C3 C11 H11A 108.9 . . ? C10 C11 H11A 108.9 . . ? C3 C11 H11B 108.9 . . ? C10 C11 H11B 108.9 . . ? H11A C11 H11B 107.7 . . ? C6 C12 H12A 109.5 . . ? C6 C12 H12B 109.5 . . ? H12A C12 H12B 109.5 . . ? C6 C12 H12C 109.5 . . ? H12A C12 H12C 109.5 . . ? H12B C12 H12C 109.5 . . ? C3 O1 C1 106.61(17) . . ? C2 O2 C3 108.22(17) . . ? _diffrn_measured_fraction_theta_max 0.992 _diffrn_reflns_theta_full 62.70 _diffrn_measured_fraction_theta_full 0.992 _refine_diff_density_max 0.179 _refine_diff_density_min -0.137 _refine_diff_density_rms 0.035 #============================================================================== data_10 _database_code_depnum_ccdc_archive 'CCDC 855565' #TrackingRef '- Hydrindanes.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C13 H18 O4 S' _chemical_formula_sum 'C13 H18 O4 S' _chemical_formula_weight 270.33 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 Monoclinic _symmetry_space_group_name_H-M 'P 2(1)/n' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, y+1/2, -z+1/2' '-x, -y, -z' 'x-1/2, -y-1/2, z-1/2' _cell_length_a 10.05890(10) _cell_length_b 10.53230(10) _cell_length_c 12.30560(10) _cell_angle_alpha 90.00 _cell_angle_beta 100.6460(10) _cell_angle_gamma 90.00 _cell_volume 1281.26(2) _cell_formula_units_Z 4 _cell_measurement_temperature 120(2) _cell_measurement_reflns_used 8990 _cell_measurement_theta_min 3.655 _cell_measurement_theta_max 70.931 _exptl_crystal_description Block _exptl_crystal_colour Colourless _exptl_crystal_size_max 0.26 _exptl_crystal_size_mid 0.22 _exptl_crystal_size_min 0.14 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.401 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 576 _exptl_absorpt_coefficient_mu 2.300 _exptl_absorpt_correction_type Multi-scan _exptl_absorpt_correction_T_min 0.5862 _exptl_absorpt_correction_T_max 0.7390 _exptl_absorpt_process_details 'SADABS V2.07 (Sheldrick, G.M., 2007)' _exptl_special_details ; SADABS was used to perform the Absorption correction Parameter refinement on 9228 reflections reduced R(int) from 0.0329 to 0.0205 Ratio of minimum to maximum apparent transmission: 0.866571 The given Tmin and Tmax were generated using the SHELX SIZE command. ; _diffrn_ambient_temperature 120(2) _diffrn_radiation_wavelength 1.54178 _diffrn_radiation_type CuK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Bruker SMART 6000' _diffrn_measurement_method 'Omega scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 10547 _diffrn_reflns_av_R_equivalents 0.0207 _diffrn_reflns_av_sigmaI/netI 0.0148 _diffrn_reflns_limit_h_min -12 _diffrn_reflns_limit_h_max 11 _diffrn_reflns_limit_k_min -12 _diffrn_reflns_limit_k_max 12 _diffrn_reflns_limit_l_min -14 _diffrn_reflns_limit_l_max 13 _diffrn_reflns_theta_min 6.71 _diffrn_reflns_theta_max 70.05 _reflns_number_total 2390 _reflns_number_gt 2308 _reflns_threshold_expression >2\s(I) _computing_data_collection 'SMART V5.626 (Bruker, 1997)' _computing_cell_refinement 'SAINT V6.28A (Bruker, 1997)' _computing_data_reduction 'SAINT V6.28A (Bruker, 1997)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 2008)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _computing_molecular_graphics ; OLEX2 (Dolomanov, O.V., Bourhis, L.J., Gildea, R.J., Howard, J.A.K, & Puschmann, H., 2009) ; _computing_publication_material 'WinGX (Farrugia, 1999)' _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^ > 2\s(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^)+(0.0536P)^2^+0.5297P] 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 2390 _refine_ls_number_parameters 164 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0314 _refine_ls_R_factor_gt 0.0306 _refine_ls_wR_factor_ref 0.0857 _refine_ls_wR_factor_gt 0.0849 _refine_ls_goodness_of_fit_ref 1.018 _refine_ls_restrained_S_all 1.018 _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 C1 C 0.21620(13) 0.46372(12) 0.47357(10) 0.0195(3) Uani 1 1 d . . . C2 C 0.37145(12) 0.30265(12) 0.50810(11) 0.0194(3) Uani 1 1 d . . . H2 H 0.4096 0.2580 0.5787 0.023 Uiso 1 1 calc R . . C3 C 0.46504(13) 0.29167(13) 0.42399(12) 0.0244(3) Uani 1 1 d . . . H3A H 0.5310 0.2220 0.4441 0.029 Uiso 1 1 calc R . . H3B H 0.5150 0.3719 0.4195 0.029 Uiso 1 1 calc R . . C4 C 0.37045(13) 0.26349(12) 0.31411(11) 0.0214(3) Uani 1 1 d . . . H4A H 0.4187 0.2165 0.2635 0.026 Uiso 1 1 calc R . . H4B H 0.3337 0.3431 0.2776 0.026 Uiso 1 1 calc R . . C5 C 0.25651(12) 0.18182(11) 0.34587(10) 0.0169(3) Uani 1 1 d . . . C6 C 0.23344(12) 0.24640(11) 0.45346(10) 0.0162(3) Uani 1 1 d . . . C7 C 0.15912(12) 0.16891(12) 0.52754(10) 0.0179(3) Uani 1 1 d . . . H7A H 0.0626 0.1616 0.4924 0.021 Uiso 1 1 calc R . . H7B H 0.1639 0.2133 0.5991 0.021 Uiso 1 1 calc R . . C8 C 0.21966(12) 0.03620(12) 0.54840(10) 0.0189(3) Uani 1 1 d . . . C9 C 0.22292(13) -0.03086(12) 0.44009(11) 0.0202(3) Uani 1 1 d . . . H9A H 0.1297 -0.0399 0.3976 0.024 Uiso 1 1 calc R . . H9B H 0.2618 -0.1169 0.4549 0.024 Uiso 1 1 calc R . . C10 C 0.30850(12) 0.04532(11) 0.37264(10) 0.0186(3) Uani 1 1 d . . . H10A H 0.3102 0.0000 0.3024 0.022 Uiso 1 1 calc R . . H10B H 0.4026 0.0495 0.4142 0.022 Uiso 1 1 calc R . . C11 C 0.12889(13) 0.18012(13) 0.25646(10) 0.0221(3) Uani 1 1 d . . . H11A H 0.0589 0.1295 0.2820 0.033 Uiso 1 1 calc R . . H11B H 0.1498 0.1426 0.1887 0.033 Uiso 1 1 calc R . . H11C H 0.0962 0.2672 0.2414 0.033 Uiso 1 1 calc R . . C12 C 0.23331(15) -0.08293(18) 0.70725(13) 0.0368(4) Uani 1 1 d . . . H12A H 0.2656 -0.1683 0.6908 0.044 Uiso 1 1 calc R . . H12B H 0.1909 -0.0879 0.7736 0.044 Uiso 1 1 calc R . . C13 C 0.34693(14) 0.01267(16) 0.72272(11) 0.0305(3) Uani 1 1 d . . . H13A H 0.3246 0.0888 0.7630 0.037 Uiso 1 1 calc R . . H13B H 0.4325 -0.0247 0.7626 0.037 Uiso 1 1 calc R . . O1 O 0.34019(9) 0.43527(9) 0.52745(7) 0.0220(2) Uani 1 1 d . . . O2 O 0.15300(8) 0.36289(8) 0.42404(7) 0.0191(2) Uani 1 1 d . . . O3 O 0.14150(9) -0.03234(9) 0.61468(8) 0.0237(2) Uani 1 1 d . . . O4 O 0.35470(9) 0.04198(9) 0.61083(7) 0.0224(2) Uani 1 1 d . . . S1 S 0.15127(3) 0.60592(3) 0.47021(3) 0.02500(13) 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 0.0229(6) 0.0193(6) 0.0173(6) -0.0005(5) 0.0065(5) -0.0026(5) C2 0.0185(6) 0.0156(6) 0.0221(6) -0.0012(5) -0.0014(5) -0.0018(5) C3 0.0174(6) 0.0227(7) 0.0330(7) -0.0034(5) 0.0048(5) -0.0036(5) C4 0.0208(6) 0.0209(6) 0.0238(7) 0.0025(5) 0.0076(5) -0.0002(5) C5 0.0163(6) 0.0182(6) 0.0159(6) -0.0001(5) 0.0023(4) -0.0003(4) C6 0.0153(5) 0.0148(6) 0.0173(6) 0.0002(4) 0.0001(4) 0.0014(4) C7 0.0173(6) 0.0196(6) 0.0167(6) -0.0006(5) 0.0027(4) -0.0004(5) C8 0.0165(6) 0.0207(6) 0.0190(6) 0.0041(5) 0.0021(5) -0.0022(5) C9 0.0210(6) 0.0162(6) 0.0231(6) 0.0007(5) 0.0033(5) -0.0005(5) C10 0.0191(6) 0.0167(6) 0.0202(6) -0.0020(5) 0.0042(5) 0.0007(4) C11 0.0200(6) 0.0283(7) 0.0166(6) -0.0011(5) -0.0002(5) 0.0008(5) C12 0.0297(8) 0.0508(9) 0.0291(8) 0.0194(7) 0.0038(6) -0.0014(7) C13 0.0244(7) 0.0467(9) 0.0190(7) 0.0064(6) 0.0003(5) 0.0012(6) O1 0.0224(5) 0.0175(5) 0.0246(5) -0.0042(3) 0.0002(4) -0.0026(3) O2 0.0189(4) 0.0156(4) 0.0217(5) -0.0009(3) 0.0005(3) 0.0016(3) O3 0.0202(4) 0.0286(5) 0.0224(5) 0.0090(4) 0.0038(4) -0.0033(4) O4 0.0176(4) 0.0289(5) 0.0195(5) 0.0066(4) -0.0001(3) -0.0010(3) S1 0.0308(2) 0.01632(19) 0.0294(2) -0.00026(11) 0.00953(14) 0.00165(12) _geom_special_details ; All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell s.u.'s are taken into account individually in the estimation of s.u.'s in distances, angles and torsion angles; correlations between s.u.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell s.u.'s is used for estimating s.u.'s 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 O2 1.3267(15) . ? C1 O1 1.3340(16) . ? C1 S1 1.6314(13) . ? C2 O1 1.4609(15) . ? C2 C3 1.5267(18) . ? C2 C6 1.5445(16) . ? C2 H2 1.0000 . ? C3 C4 1.5318(18) . ? C3 H3A 0.9900 . ? C3 H3B 0.9900 . ? C4 C5 1.5400(16) . ? C4 H4A 0.9900 . ? C4 H4B 0.9900 . ? C5 C11 1.5287(16) . ? C5 C10 1.5444(17) . ? C5 C6 1.5437(16) . ? C6 O2 1.4775(14) . ? C6 C7 1.5191(16) . ? C7 C8 1.5273(17) . ? C7 H7A 0.9900 . ? C7 H7B 0.9900 . ? C8 O3 1.4288(15) . ? C8 O4 1.4331(15) . ? C8 C9 1.5140(18) . ? C9 C10 1.5290(17) . ? C9 H9A 0.9900 . ? C9 H9B 0.9900 . ? C10 H10A 0.9900 . ? C10 H10B 0.9900 . ? C11 H11A 0.9800 . ? C11 H11B 0.9800 . ? C11 H11C 0.9800 . ? C12 O3 1.4303(17) . ? C12 C13 1.509(2) . ? C12 H12A 0.9900 . ? C12 H12B 0.9900 . ? C13 O4 1.4272(16) . ? C13 H13A 0.9900 . ? C13 H13B 0.9900 . ? 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 O2 C1 O1 111.91(10) . . ? O2 C1 S1 124.58(10) . . ? O1 C1 S1 123.51(10) . . ? O1 C2 C3 111.17(10) . . ? O1 C2 C6 103.57(9) . . ? C3 C2 C6 107.04(10) . . ? O1 C2 H2 111.6 . . ? C3 C2 H2 111.6 . . ? C6 C2 H2 111.6 . . ? C2 C3 C4 104.65(10) . . ? C2 C3 H3A 110.8 . . ? C4 C3 H3A 110.8 . . ? C2 C3 H3B 110.8 . . ? C4 C3 H3B 110.8 . . ? H3A C3 H3B 108.9 . . ? C3 C4 C5 104.73(10) . . ? C3 C4 H4A 110.8 . . ? C5 C4 H4A 110.8 . . ? C3 C4 H4B 110.8 . . ? C5 C4 H4B 110.8 . . ? H4A C4 H4B 108.9 . . ? C11 C5 C4 112.91(10) . . ? C11 C5 C10 110.42(10) . . ? C4 C5 C10 109.60(10) . . ? C11 C5 C6 112.53(10) . . ? C4 C5 C6 102.03(9) . . ? C10 C5 C6 109.02(10) . . ? O2 C6 C7 106.57(9) . . ? O2 C6 C2 101.28(9) . . ? C7 C6 C2 116.57(10) . . ? O2 C6 C5 108.54(9) . . ? C7 C6 C5 116.53(10) . . ? C2 C6 C5 106.07(9) . . ? C6 C7 C8 111.55(10) . . ? C6 C7 H7A 109.3 . . ? C8 C7 H7A 109.3 . . ? C6 C7 H7B 109.3 . . ? C8 C7 H7B 109.3 . . ? H7A C7 H7B 108.0 . . ? O3 C8 O4 106.41(9) . . ? O3 C8 C9 111.75(10) . . ? O4 C8 C9 108.61(10) . . ? O3 C8 C7 108.30(10) . . ? O4 C8 C7 111.11(10) . . ? C9 C8 C7 110.60(10) . . ? C8 C9 C10 109.82(10) . . ? C8 C9 H9A 109.7 . . ? C10 C9 H9A 109.7 . . ? C8 C9 H9B 109.7 . . ? C10 C9 H9B 109.7 . . ? H9A C9 H9B 108.2 . . ? C9 C10 C5 113.69(10) . . ? C9 C10 H10A 108.8 . . ? C5 C10 H10A 108.8 . . ? C9 C10 H10B 108.8 . . ? C5 C10 H10B 108.8 . . ? H10A C10 H10B 107.7 . . ? C5 C11 H11A 109.5 . . ? C5 C11 H11B 109.5 . . ? H11A C11 H11B 109.5 . . ? C5 C11 H11C 109.5 . . ? H11A C11 H11C 109.5 . . ? H11B C11 H11C 109.5 . . ? O3 C12 C13 102.39(12) . . ? O3 C12 H12A 111.3 . . ? C13 C12 H12A 111.3 . . ? O3 C12 H12B 111.3 . . ? C13 C12 H12B 111.3 . . ? H12A C12 H12B 109.2 . . ? O4 C13 C12 101.41(11) . . ? O4 C13 H13A 111.5 . . ? C12 C13 H13A 111.5 . . ? O4 C13 H13B 111.5 . . ? C12 C13 H13B 111.5 . . ? H13A C13 H13B 109.3 . . ? C1 O1 C2 110.08(9) . . ? C1 O2 C6 110.97(9) . . ? C8 O3 C12 107.49(10) . . ? C13 O4 C8 107.01(9) . . ? 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 _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag O1 C2 C3 C4 -97.68(11) . . . . ? C6 C2 C3 C4 14.76(13) . . . . ? C2 C3 C4 C5 -34.08(13) . . . . ? C3 C4 C5 C11 160.68(11) . . . . ? C3 C4 C5 C10 -75.78(12) . . . . ? C3 C4 C5 C6 39.66(12) . . . . ? O1 C2 C6 O2 14.12(11) . . . . ? C3 C2 C6 O2 -103.43(10) . . . . ? O1 C2 C6 C7 -101.03(11) . . . . ? C3 C2 C6 C7 141.42(11) . . . . ? O1 C2 C6 C5 127.38(10) . . . . ? C3 C2 C6 C5 9.83(13) . . . . ? C11 C5 C6 O2 -43.28(13) . . . . ? C4 C5 C6 O2 78.00(11) . . . . ? C10 C5 C6 O2 -166.13(9) . . . . ? C11 C5 C6 C7 76.96(13) . . . . ? C4 C5 C6 C7 -161.75(10) . . . . ? C10 C5 C6 C7 -45.89(13) . . . . ? C11 C5 C6 C2 -151.42(10) . . . . ? C4 C5 C6 C2 -30.14(11) . . . . ? C10 C5 C6 C2 85.73(11) . . . . ? O2 C6 C7 C8 170.68(9) . . . . ? C2 C6 C7 C8 -77.17(13) . . . . ? C5 C6 C7 C8 49.39(14) . . . . ? C6 C7 C8 O3 -177.72(9) . . . . ? C6 C7 C8 O4 65.76(13) . . . . ? C6 C7 C8 C9 -54.95(13) . . . . ? O3 C8 C9 C10 -179.53(10) . . . . ? O4 C8 C9 C10 -62.44(12) . . . . ? C7 C8 C9 C10 59.74(13) . . . . ? C8 C9 C10 C5 -58.95(13) . . . . ? C11 C5 C10 C9 -73.92(13) . . . . ? C4 C5 C10 C9 161.09(10) . . . . ? C6 C5 C10 C9 50.19(13) . . . . ? O3 C12 C13 O4 -38.53(15) . . . . ? O2 C1 O1 C2 4.17(14) . . . . ? S1 C1 O1 C2 -176.07(9) . . . . ? C3 C2 O1 C1 102.73(11) . . . . ? C6 C2 O1 C1 -11.90(13) . . . . ? O1 C1 O2 C6 6.14(14) . . . . ? S1 C1 O2 C6 -173.62(9) . . . . ? C7 C6 O2 C1 109.55(11) . . . . ? C2 C6 O2 C1 -12.81(12) . . . . ? C5 C6 O2 C1 -124.20(10) . . . . ? O4 C8 O3 C12 -8.61(14) . . . . ? C9 C8 O3 C12 109.80(13) . . . . ? C7 C8 O3 C12 -128.13(12) . . . . ? C13 C12 O3 C8 29.16(15) . . . . ? C12 C13 O4 C8 34.23(14) . . . . ? O3 C8 O4 C13 -17.11(14) . . . . ? C9 C8 O4 C13 -137.57(11) . . . . ? C7 C8 O4 C13 100.56(12) . . . . ? _diffrn_measured_fraction_theta_max 0.982 _diffrn_reflns_theta_full 70.05 _diffrn_measured_fraction_theta_full 0.982 _refine_diff_density_max 0.258 _refine_diff_density_min -0.297 _refine_diff_density_rms 0.089 #==========================================================================END