# 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_ha60e_0m _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C20 H22 O3 S' _chemical_formula_weight 342.44 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 ? _symmetry_space_group_name_H-M ? loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, -y, z+1/2' 'x+1/2, -y+1/2, -z' '-x, y+1/2, -z+1/2' _cell_length_a 10.3509(6) _cell_length_b 11.7545(7) _cell_length_c 15.0554(9) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 1831.79(19) _cell_formula_units_Z 4 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description ? _exptl_crystal_colour ? _exptl_crystal_size_max ? _exptl_crystal_size_mid ? _exptl_crystal_size_min ? _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.242 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 728 _exptl_absorpt_coefficient_mu 0.191 _exptl_absorpt_correction_type ? _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _exptl_absorpt_process_details ? _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 ? _diffrn_measurement_method ? _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 13190 _diffrn_reflns_av_R_equivalents 0.0429 _diffrn_reflns_av_sigmaI/netI 0.0530 _diffrn_reflns_limit_h_min -13 _diffrn_reflns_limit_h_max 13 _diffrn_reflns_limit_k_min -14 _diffrn_reflns_limit_k_max 15 _diffrn_reflns_limit_l_min -15 _diffrn_reflns_limit_l_max 19 _diffrn_reflns_theta_min 2.20 _diffrn_reflns_theta_max 27.96 _reflns_number_total 4373 _reflns_number_gt 3769 _reflns_threshold_expression >2\s(I) _computing_data_collection ? _computing_cell_refinement ? _computing_data_reduction ? _computing_structure_solution ? _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _computing_molecular_graphics ? _computing_publication_material ? _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^)+(0.0352P)^2^+0.1240P] 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 mixed _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _refine_ls_abs_structure_Flack -0.01(6) _refine_ls_number_reflns 4373 _refine_ls_number_parameters 220 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0483 _refine_ls_R_factor_gt 0.0378 _refine_ls_wR_factor_ref 0.0840 _refine_ls_wR_factor_gt 0.0793 _refine_ls_goodness_of_fit_ref 1.037 _refine_ls_restrained_S_all 1.037 _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 0.18482(19) 0.24907(18) 0.14631(15) 0.0388(5) Uani 1 1 d . . . H1 H 0.2095 0.3064 0.1854 0.047 Uiso 1 1 calc R . . C2 C 0.1921(2) 0.2638(2) 0.05434(17) 0.0563(7) Uani 1 1 d . . . H2 H 0.2230 0.3319 0.0312 0.068 Uiso 1 1 calc R . . C3 C 0.1542(3) 0.1787(2) -0.00194(17) 0.0628(8) Uani 1 1 d . . . H3 H 0.1588 0.1903 -0.0630 0.075 Uiso 1 1 calc R . . C4 C 0.1092(2) 0.0756(2) 0.03042(15) 0.0506(7) Uani 1 1 d . . . H4 H 0.0849 0.0181 -0.0086 0.061 Uiso 1 1 calc R . . C5 C 0.10064(18) 0.05913(17) 0.12099(12) 0.0317(4) Uani 1 1 d . . . C6 C 0.13963(17) 0.14632(16) 0.17642(13) 0.0280(4) Uani 1 1 d . . . C7 C 0.06143(19) -0.03963(17) 0.17817(13) 0.0317(4) Uani 1 1 d . . . H7A H 0.1261 -0.0994 0.1772 0.038 Uiso 1 1 calc R . . H7B H -0.0211 -0.0708 0.1597 0.038 Uiso 1 1 calc R . . C8 C 0.05215(15) 0.01606(14) 0.27013(12) 0.0228(4) Uani 1 1 d . . . C9 C 0.09441(17) -0.05272(15) 0.34888(12) 0.0276(4) Uani 1 1 d . . . H9A H 0.1838 -0.0756 0.3412 0.033 Uiso 1 1 calc R . . H9B H 0.0422 -0.1210 0.3529 0.033 Uiso 1 1 calc R . . C10 C 0.08106(17) 0.01588(17) 0.43474(12) 0.0293(4) Uani 1 1 d . . . H10A H 0.0836 -0.0355 0.4851 0.035 Uiso 1 1 calc R . . H10B H 0.1535 0.0678 0.4399 0.035 Uiso 1 1 calc R . . C11 C -0.04395(16) 0.08314(15) 0.43698(12) 0.0237(4) Uani 1 1 d . . . C12 C -0.11357(15) 0.10038(14) 0.35886(11) 0.0206(4) Uani 1 1 d . . . C13 C -0.22489(15) 0.16849(14) 0.35905(11) 0.0207(4) Uani 1 1 d . . . C14 C -0.26717(16) 0.21880(16) 0.43663(12) 0.0270(4) Uani 1 1 d . . . H14 H -0.3398 0.2654 0.4362 0.032 Uiso 1 1 calc R . . C15 C -0.20062(17) 0.19940(16) 0.51540(12) 0.0292(4) Uani 1 1 d . . . H15 H -0.2300 0.2308 0.5684 0.035 Uiso 1 1 calc R . . C16 C -0.08966(17) 0.13258(16) 0.51419(12) 0.0270(4) Uani 1 1 d . . . H16 H -0.0449 0.1208 0.5669 0.032 Uiso 1 1 calc R . . C17 C -0.43579(14) 0.09885(13) 0.25238(13) 0.0235(4) Uani 1 1 d . . . C18 C -0.37801(17) -0.01942(14) 0.26203(14) 0.0326(4) Uani 1 1 d . . . H18A H -0.3437 -0.0283 0.3209 0.049 Uiso 1 1 calc R . . H18B H -0.3100 -0.0291 0.2194 0.049 Uiso 1 1 calc R . . H18C H -0.4438 -0.0755 0.2520 0.049 Uiso 1 1 calc R . . C19 C -0.53356(18) 0.12698(19) 0.32411(13) 0.0336(5) Uani 1 1 d . . . H19A H -0.5623 0.2041 0.3170 0.050 Uiso 1 1 calc R . . H19B H -0.4942 0.1182 0.3814 0.050 Uiso 1 1 calc R . . H19C H -0.6061 0.0765 0.3193 0.050 Uiso 1 1 calc R . . C20 C -0.49641(17) 0.11496(18) 0.16064(13) 0.0310(5) Uani 1 1 d . . . H20A H -0.5675 0.0632 0.1538 0.046 Uiso 1 1 calc R . . H20B H -0.4329 0.1000 0.1157 0.046 Uiso 1 1 calc R . . H20C H -0.5269 0.1917 0.1549 0.046 Uiso 1 1 calc R . . O1 O 0.12942(10) 0.11840(9) 0.26535(8) 0.0246(3) Uani 1 1 d . . . O2 O -0.08055(10) 0.05159(10) 0.27909(7) 0.0230(3) Uani 1 1 d . . . O3 O -0.36320(11) 0.31846(10) 0.26974(9) 0.0313(3) Uani 1 1 d . . . S S -0.30132(3) 0.20416(3) 0.25505(3) 0.02169(10) 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 0.0287(10) 0.0357(11) 0.0519(13) 0.0126(11) 0.0091(9) 0.0053(9) C2 0.0545(14) 0.0547(15) 0.0597(16) 0.0301(14) 0.0271(13) 0.0240(12) C3 0.0792(18) 0.0733(19) 0.0359(13) 0.0232(14) 0.0247(12) 0.0465(16) C4 0.0618(15) 0.0586(15) 0.0315(12) -0.0060(12) 0.0054(11) 0.0340(13) C5 0.0289(9) 0.0382(11) 0.0281(10) 0.0007(10) 0.0053(8) 0.0158(9) C6 0.0211(8) 0.0313(10) 0.0315(11) 0.0069(9) 0.0039(7) 0.0083(8) C7 0.0302(10) 0.0285(10) 0.0363(11) -0.0075(10) -0.0015(8) 0.0093(8) C8 0.0162(7) 0.0222(8) 0.0300(10) -0.0023(8) -0.0011(7) -0.0002(6) C9 0.0206(9) 0.0240(9) 0.0381(11) 0.0053(9) 0.0021(8) 0.0020(8) C10 0.0249(9) 0.0356(11) 0.0273(10) 0.0057(9) -0.0034(8) 0.0061(8) C11 0.0183(8) 0.0246(9) 0.0281(10) 0.0042(8) -0.0013(7) -0.0014(7) C12 0.0182(8) 0.0200(8) 0.0235(9) 0.0002(8) 0.0015(7) -0.0032(6) C13 0.0170(8) 0.0203(8) 0.0247(9) -0.0012(8) -0.0025(6) -0.0027(6) C14 0.0191(8) 0.0273(10) 0.0345(10) -0.0048(9) -0.0022(7) 0.0012(7) C15 0.0257(9) 0.0345(10) 0.0275(9) -0.0081(9) -0.0008(7) -0.0002(9) C16 0.0237(8) 0.0324(10) 0.0250(9) 0.0021(9) -0.0050(7) -0.0032(8) C17 0.0179(7) 0.0254(8) 0.0271(9) -0.0022(9) -0.0020(7) -0.0037(6) C18 0.0299(9) 0.0242(9) 0.0437(12) -0.0013(10) -0.0068(9) -0.0075(7) C19 0.0247(9) 0.0463(12) 0.0299(11) -0.0042(10) 0.0042(8) -0.0106(9) C20 0.0241(10) 0.0382(12) 0.0306(11) -0.0027(10) -0.0062(8) -0.0012(8) O1 0.0211(6) 0.0244(6) 0.0282(7) 0.0022(6) -0.0002(5) -0.0024(5) O2 0.0165(5) 0.0262(6) 0.0262(7) -0.0031(6) -0.0010(5) 0.0023(5) O3 0.0289(6) 0.0217(6) 0.0434(8) 0.0006(6) -0.0088(6) 0.0041(5) S 0.01817(18) 0.02046(19) 0.0264(2) 0.0024(2) -0.00262(17) -0.00021(15) _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 C6 1.372(3) . ? C1 C2 1.397(3) . ? C2 C3 1.368(4) . ? C3 C4 1.387(4) . ? C4 C5 1.380(3) . ? C5 C6 1.382(3) . ? C5 C7 1.501(3) . ? C6 O1 1.383(2) . ? C7 C8 1.534(3) . ? C8 O2 1.4419(19) . ? C8 O1 1.4464(19) . ? C8 C9 1.500(2) . ? C9 C10 1.530(3) . ? C10 C11 1.517(2) . ? C11 C16 1.383(3) . ? C11 C12 1.394(2) . ? C12 O2 1.374(2) . ? C12 C13 1.403(2) . ? C13 C14 1.380(2) . ? C13 S 1.8037(17) . ? C14 C15 1.390(2) . ? C15 C16 1.392(3) . ? C17 C19 1.516(3) . ? C17 C18 1.520(2) . ? C17 C20 1.529(3) . ? C17 S 1.8632(15) . ? O3 S 1.5047(12) . ? 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 C6 C1 C2 117.0(2) . . ? C3 C2 C1 120.5(2) . . ? C2 C3 C4 121.2(2) . . ? C5 C4 C3 119.4(2) . . ? C4 C5 C6 118.3(2) . . ? C4 C5 C7 133.8(2) . . ? C6 C5 C7 107.83(16) . . ? C1 C6 C5 123.56(19) . . ? C1 C6 O1 123.70(18) . . ? C5 C6 O1 112.73(16) . . ? C5 C7 C8 101.80(15) . . ? O2 C8 O1 106.88(12) . . ? O2 C8 C9 111.10(14) . . ? O1 C8 C9 109.04(13) . . ? O2 C8 C7 105.53(13) . . ? O1 C8 C7 105.98(14) . . ? C9 C8 C7 117.70(14) . . ? C8 C9 C10 110.94(14) . . ? C11 C10 C9 111.76(15) . . ? C16 C11 C12 118.10(16) . . ? C16 C11 C10 121.98(16) . . ? C12 C11 C10 119.87(16) . . ? O2 C12 C11 123.23(15) . . ? O2 C12 C13 116.38(14) . . ? C11 C12 C13 120.38(16) . . ? C14 C13 C12 120.43(15) . . ? C14 C13 S 119.73(13) . . ? C12 C13 S 119.41(13) . . ? C13 C14 C15 119.63(16) . . ? C14 C15 C16 119.37(16) . . ? C11 C16 C15 122.04(16) . . ? C19 C17 C18 113.19(17) . . ? C19 C17 C20 110.03(15) . . ? C18 C17 C20 111.17(16) . . ? C19 C17 S 109.77(12) . . ? C18 C17 S 108.16(11) . . ? C20 C17 S 104.11(12) . . ? C6 O1 C8 106.73(13) . . ? C12 O2 C8 116.08(12) . . ? O3 S C13 105.46(7) . . ? O3 S C17 106.17(7) . . ? C13 S C17 101.07(8) . . ? _diffrn_measured_fraction_theta_max 0.998 _diffrn_reflns_theta_full 27.96 _diffrn_measured_fraction_theta_full 0.998 _refine_diff_density_max 0.231 _refine_diff_density_min -0.205 _refine_diff_density_rms 0.042 _database_code_depnum_ccdc_archive 'CCDC 940550' ####################################################################### # # 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_ha1_0m _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C20 H22 O3 S' _chemical_formula_weight 342.44 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 ? _symmetry_space_group_name_H-M ? loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z' _cell_length_a 8.5909(4) _cell_length_b 10.8998(5) _cell_length_c 9.6997(4) _cell_angle_alpha 90.00 _cell_angle_beta 104.215(3) _cell_angle_gamma 90.00 _cell_volume 880.46(7) _cell_formula_units_Z 2 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description ? _exptl_crystal_colour ? _exptl_crystal_size_max ? _exptl_crystal_size_mid ? _exptl_crystal_size_min ? _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.292 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 364 _exptl_absorpt_coefficient_mu 0.198 _exptl_absorpt_correction_type ? _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _exptl_absorpt_process_details ? _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 ? _diffrn_measurement_method ? _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 10924 _diffrn_reflns_av_R_equivalents 0.0365 _diffrn_reflns_av_sigmaI/netI 0.0475 _diffrn_reflns_limit_h_min -11 _diffrn_reflns_limit_h_max 11 _diffrn_reflns_limit_k_min -14 _diffrn_reflns_limit_k_max 14 _diffrn_reflns_limit_l_min -12 _diffrn_reflns_limit_l_max 12 _diffrn_reflns_theta_min 2.17 _diffrn_reflns_theta_max 27.91 _reflns_number_total 4120 _reflns_number_gt 3764 _reflns_threshold_expression >2\s(I) _computing_data_collection ? _computing_cell_refinement ? _computing_data_reduction ? _computing_structure_solution ? _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _computing_molecular_graphics ? _computing_publication_material ? _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^)+(0.0377P)^2^+0.0736P] 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 mixed _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _refine_ls_abs_structure_Flack -0.01(6) _refine_ls_number_reflns 4120 _refine_ls_number_parameters 220 _refine_ls_number_restraints 1 _refine_ls_R_factor_all 0.0408 _refine_ls_R_factor_gt 0.0355 _refine_ls_wR_factor_ref 0.0818 _refine_ls_wR_factor_gt 0.0785 _refine_ls_goodness_of_fit_ref 1.038 _refine_ls_restrained_S_all 1.037 _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 0.3329(2) 0.03672(18) 0.58772(17) 0.0241(4) Uani 1 1 d . . . H1 H 0.3317 -0.0458 0.6119 0.029 Uiso 1 1 calc R . . C2 C 0.1942(2) 0.09884(19) 0.52160(18) 0.0288(4) Uani 1 1 d . . . H2 H 0.0973 0.0564 0.4986 0.035 Uiso 1 1 calc R . . C3 C 0.1955(2) 0.2233(2) 0.48840(19) 0.0327(5) Uani 1 1 d . . . H3 H 0.1000 0.2629 0.4453 0.039 Uiso 1 1 calc R . . C4 C 0.3396(2) 0.28843(19) 0.51980(19) 0.0305(4) Uani 1 1 d . . . H4 H 0.3414 0.3714 0.4981 0.037 Uiso 1 1 calc R . . C5 C 0.4795(2) 0.22737(17) 0.58369(16) 0.0237(4) Uani 1 1 d . . . C6 C 0.6540(2) 0.26547(17) 0.62652(18) 0.0253(4) Uani 1 1 d . . . H6A H 0.6681 0.3404 0.6821 0.030 Uiso 1 1 calc R . . H6B H 0.6972 0.2770 0.5440 0.030 Uiso 1 1 calc R . . C7 C 0.7324(2) 0.15653(17) 0.71555(18) 0.0225(4) Uani 1 1 d . . . C8 C 0.4730(2) 0.10384(17) 0.61577(17) 0.0214(4) Uani 1 1 d . . . C9 C 0.8936(2) 0.11382(19) 0.6978(2) 0.0316(4) Uani 1 1 d . . . H9A H 0.9718 0.1790 0.7260 0.038 Uiso 1 1 calc R . . H9B H 0.8855 0.0950 0.5986 0.038 Uiso 1 1 calc R . . C10 C 0.9495(2) 0.00039(18) 0.7880(2) 0.0305(4) Uani 1 1 d . . . H10A H 0.8890 -0.0705 0.7438 0.037 Uiso 1 1 calc R . . H10B H 1.0621 -0.0143 0.7932 0.037 Uiso 1 1 calc R . . C11 C 0.9264(2) 0.01676(17) 0.9361(2) 0.0259(4) Uani 1 1 d . . . C12 C 0.8209(2) 0.10618(16) 0.96282(18) 0.0212(4) Uani 1 1 d . . . C13 C 0.7948(2) 0.11931(16) 1.09881(18) 0.0234(4) Uani 1 1 d . . . C14 C 0.8748(2) 0.0451(2) 1.2089(2) 0.0315(4) Uani 1 1 d . . . H14 H 0.8585 0.0548 1.2996 0.038 Uiso 1 1 calc R . . C15 C 0.9799(3) -0.0442(2) 1.1834(2) 0.0402(5) Uani 1 1 d . . . H15 H 1.0335 -0.0949 1.2568 0.048 Uiso 1 1 calc R . . C16 C 1.0045(2) -0.05739(19) 1.0485(2) 0.0352(5) Uani 1 1 d . . . H16 H 1.0751 -0.1174 1.0326 0.042 Uiso 1 1 calc R . . C17 C 0.4723(2) 0.16840(18) 1.10749(19) 0.0241(4) Uani 1 1 d . . . C18 C 0.4778(3) 0.0617(2) 1.2086(2) 0.0371(5) Uani 1 1 d . . . H18A H 0.3704 0.0349 1.2050 0.056 Uiso 1 1 calc R . . H18B H 0.5292 0.0872 1.3036 0.056 Uiso 1 1 calc R . . H18C H 0.5373 -0.0046 1.1812 0.056 Uiso 1 1 calc R . . C19 C 0.3649(2) 0.2715(2) 1.1390(2) 0.0360(5) Uani 1 1 d . . . H19A H 0.3666 0.3392 1.0760 0.054 Uiso 1 1 calc R . . H19B H 0.4039 0.2981 1.2357 0.054 Uiso 1 1 calc R . . H19C H 0.2569 0.2419 1.1249 0.054 Uiso 1 1 calc R . . C20 C 0.4179(2) 0.12985(19) 0.95208(19) 0.0283(4) Uani 1 1 d . . . H20A H 0.4810 0.0614 0.9353 0.042 Uiso 1 1 calc R . . H20B H 0.4316 0.1971 0.8923 0.042 Uiso 1 1 calc R . . H20C H 0.3067 0.1068 0.9307 0.042 Uiso 1 1 calc R . . O1 O 0.62226(14) 0.05464(12) 0.67898(13) 0.0240(3) Uani 1 1 d . . . O2 O 0.74159(14) 0.18768(11) 0.86127(12) 0.0209(3) Uani 1 1 d . . . O3 O 0.72956(15) 0.25924(14) 1.29739(12) 0.0331(3) Uani 1 1 d . . . S S 0.67368(5) 0.24277(4) 1.13923(4) 0.02198(10) 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 0.0286(9) 0.0238(9) 0.0208(8) -0.0033(7) 0.0080(7) -0.0029(8) C2 0.0256(9) 0.0398(12) 0.0221(8) -0.0006(8) 0.0082(7) -0.0027(8) C3 0.0305(10) 0.0408(13) 0.0261(8) 0.0054(9) 0.0057(7) 0.0066(9) C4 0.0409(11) 0.0275(10) 0.0247(9) 0.0081(8) 0.0113(8) 0.0054(9) C5 0.0304(9) 0.0244(10) 0.0176(7) -0.0010(7) 0.0083(7) -0.0019(8) C6 0.0335(10) 0.0225(12) 0.0232(8) -0.0002(7) 0.0130(7) -0.0066(8) C7 0.0244(9) 0.0217(9) 0.0229(8) -0.0054(7) 0.0088(7) -0.0076(7) C8 0.0245(9) 0.0232(9) 0.0178(7) -0.0045(7) 0.0079(7) 0.0000(7) C9 0.0283(10) 0.0347(11) 0.0366(10) -0.0094(9) 0.0169(8) -0.0045(9) C10 0.0209(10) 0.0312(11) 0.0399(11) -0.0140(9) 0.0087(8) 0.0008(8) C11 0.0187(9) 0.0234(10) 0.0336(10) -0.0100(8) 0.0027(8) -0.0012(7) C12 0.0170(8) 0.0191(8) 0.0254(8) -0.0038(7) 0.0011(7) -0.0033(7) C13 0.0214(9) 0.0207(9) 0.0256(8) -0.0054(7) 0.0008(7) 0.0026(7) C14 0.0351(11) 0.0305(11) 0.0237(9) -0.0005(8) -0.0025(8) 0.0069(9) C15 0.0378(12) 0.0347(12) 0.0386(12) -0.0008(10) -0.0087(9) 0.0156(10) C16 0.0274(10) 0.0259(11) 0.0460(12) -0.0117(10) -0.0031(9) 0.0092(9) C17 0.0229(9) 0.0269(10) 0.0234(8) -0.0002(7) 0.0074(7) 0.0007(8) C18 0.0398(12) 0.0353(12) 0.0378(11) 0.0078(9) 0.0124(9) -0.0059(10) C19 0.0307(10) 0.0423(14) 0.0380(10) -0.0042(9) 0.0142(8) 0.0067(9) C20 0.0235(9) 0.0342(11) 0.0266(9) -0.0049(8) 0.0050(7) -0.0022(8) O1 0.0231(6) 0.0201(6) 0.0279(6) -0.0049(5) 0.0047(5) -0.0023(5) O2 0.0217(6) 0.0193(6) 0.0224(6) -0.0035(5) 0.0069(5) 0.0005(5) O3 0.0379(7) 0.0365(9) 0.0233(6) -0.0101(6) 0.0046(5) 0.0032(7) S 0.0255(2) 0.0187(2) 0.02147(18) -0.00335(18) 0.00523(15) 0.00213(19) _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 C8 1.377(2) . ? C1 C2 1.384(3) . ? C2 C3 1.395(3) . ? C3 C4 1.394(3) . ? C4 C5 1.381(3) . ? C5 C8 1.386(3) . ? C5 C6 1.512(3) . ? C6 C7 1.524(3) . ? C7 O2 1.4368(19) . ? C7 O1 1.445(2) . ? C7 C9 1.510(2) . ? C8 O1 1.386(2) . ? C9 C10 1.523(3) . ? C10 C11 1.507(3) . ? C11 C16 1.391(3) . ? C11 C12 1.398(2) . ? C12 O2 1.376(2) . ? C12 C13 1.398(2) . ? C13 C14 1.381(3) . ? C13 S 1.8023(18) . ? C14 C15 1.391(3) . ? C15 C16 1.383(3) . ? C17 C18 1.514(3) . ? C17 C20 1.524(2) . ? C17 C19 1.532(3) . ? C17 S 1.8667(18) . ? O3 S 1.5015(12) . ? 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 C8 C1 C2 116.30(18) . . ? C1 C2 C3 121.88(19) . . ? C4 C3 C2 120.10(19) . . ? C5 C4 C3 118.77(18) . . ? C4 C5 C8 119.37(17) . . ? C4 C5 C6 133.33(17) . . ? C8 C5 C6 107.27(16) . . ? C5 C6 C7 102.23(14) . . ? O2 C7 O1 107.32(12) . . ? O2 C7 C9 110.74(14) . . ? O1 C7 C9 107.36(14) . . ? O2 C7 C6 106.45(14) . . ? O1 C7 C6 106.75(13) . . ? C9 C7 C6 117.73(15) . . ? C1 C8 O1 123.39(17) . . ? C1 C8 C5 123.57(17) . . ? O1 C8 C5 113.04(15) . . ? C7 C9 C10 110.71(15) . . ? C11 C10 C9 110.76(15) . . ? C16 C11 C12 118.00(17) . . ? C16 C11 C10 121.82(16) . . ? C12 C11 C10 120.15(16) . . ? O2 C12 C11 123.14(15) . . ? O2 C12 C13 116.31(15) . . ? C11 C12 C13 120.52(16) . . ? C14 C13 C12 120.36(17) . . ? C14 C13 S 118.24(14) . . ? C12 C13 S 121.09(14) . . ? C13 C14 C15 119.55(18) . . ? C16 C15 C14 119.90(19) . . ? C15 C16 C11 121.67(18) . . ? C18 C17 C20 112.47(17) . . ? C18 C17 C19 111.05(15) . . ? C20 C17 C19 110.25(15) . . ? C18 C17 S 110.26(13) . . ? C20 C17 S 109.25(12) . . ? C19 C17 S 103.16(13) . . ? C8 O1 C7 106.85(13) . . ? C12 O2 C7 116.72(13) . . ? O3 S C13 104.76(8) . . ? O3 S C17 105.74(8) . . ? C13 S C17 101.62(8) . . ? _diffrn_measured_fraction_theta_max 0.997 _diffrn_reflns_theta_full 27.91 _diffrn_measured_fraction_theta_full 0.997 _refine_diff_density_max 0.270 _refine_diff_density_min -0.209 _refine_diff_density_rms 0.042 _database_code_depnum_ccdc_archive 'CCDC 940551'