# Supplementary Material (ESI) for Chemical Communications # This journal is © The Royal Society of Chemistry 2003 data_global _journal_coden_Cambridge 182 loop_ _publ_author_name 'S. Warren' 'Julie Carlisle' 'David J. Fox' _publ_contact_author_name 'Dr S Warren' _publ_contact_author_address ; University Chemical Laboratory Cambridge University Lensfield Road CAMBRIDGE CB2 1EW UK ; _publ_contact_author_email SW134@CAM.AC.UK _publ_requested_journal 'Chemical Communications' _publ_section_title ; Thermodynamically controlled cyclisation reactions with double phenylsulfanyl migration ; data_sw0207 _database_code_CSD 216120 _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C24 H30 O2 S2' _chemical_formula_sum 'C24 H30 O2 S2' _chemical_formula_weight 414.60 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 Monoclinic _symmetry_space_group_name_H-M P2(1)/c loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y-1/2, z-1/2' _cell_length_a 7.2728(4) _cell_length_b 5.6573(3) _cell_length_c 26.5782(16) _cell_angle_alpha 90.00 _cell_angle_beta 96.130(2) _cell_angle_gamma 90.00 _cell_volume 1087.29(11) _cell_formula_units_Z 2 _cell_measurement_temperature 180(2) _cell_measurement_reflns_used 31844 _cell_measurement_theta_min 1.0 _cell_measurement_theta_max 25.03 _exptl_crystal_description ? _exptl_crystal_colour ? _exptl_crystal_size_max 0.23 _exptl_crystal_size_mid 0.18 _exptl_crystal_size_min 0.10 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.266 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 444 _exptl_absorpt_coefficient_mu 0.262 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.838 _exptl_absorpt_correction_T_max 0.977 _exptl_absorpt_process_details ; multi-scan from symmetry-related measurements Sortav (Blessing 1995) ; _exptl_special_details ; ? ; _diffrn_ambient_temperature 180(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_measurement_device_type 'Nonius Kappa CCD' _diffrn_measurement_method 'Thin slice \w and \f scans' _diffrn_standards_number 0 _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 5145 _diffrn_reflns_av_R_equivalents 0.0435 _diffrn_reflns_av_sigmaI/netI 0.0445 _diffrn_reflns_limit_h_min -8 _diffrn_reflns_limit_h_max 8 _diffrn_reflns_limit_k_min -6 _diffrn_reflns_limit_k_max 6 _diffrn_reflns_limit_l_min -31 _diffrn_reflns_limit_l_max 31 _diffrn_reflns_theta_min 3.68 _diffrn_reflns_theta_max 25.03 _reflns_number_total 1861 _reflns_number_gt 1553 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Collect (Nonius B.V. 1998)' _computing_cell_refinement 'HKL Scalepack (Otwinowski & Minor 1997)' _computing_data_reduction ; HKL Denzo and Scalepack (Otwinowski & Minor 1997) ; _computing_structure_solution 'SIR-92 (Altomare et al. 1994)' _computing_structure_refinement 'SHELXL-97 (Sheldrick 1997)' _computing_publication_material 'SHELXL-97 (Sheldrick 1997)' _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^)+(0.0405P)^2^+1.0992P] 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_number_reflns 1861 _refine_ls_number_parameters 129 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0616 _refine_ls_R_factor_gt 0.0496 _refine_ls_wR_factor_ref 0.1211 _refine_ls_wR_factor_gt 0.1139 _refine_ls_goodness_of_fit_ref 1.056 _refine_ls_restrained_S_all 1.056 _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 -0.16407(9) 0.86494(13) -0.13929(3) 0.0397(2) Uani 1 1 d . . . O1 O 0.2360(2) 0.5809(3) 0.02306(6) 0.0370(5) Uani 1 1 d . . . C1 C 0.0866(3) 0.5159(5) -0.01265(9) 0.0336(6) Uani 1 1 d . . . H1 H 0.1170 0.3635 -0.0290 0.040 Uiso 1 1 calc R . . C2 C 0.0531(3) 0.7059(5) -0.05332(10) 0.0367(6) Uani 1 1 d . . . H2A H 0.0315 0.8600 -0.0373 0.044 Uiso 1 1 calc R . . H2B H 0.1635 0.7210 -0.0719 0.044 Uiso 1 1 calc R . . C3 C -0.1140(3) 0.6404(5) -0.08998(9) 0.0330(6) Uani 1 1 d . . . H3 H -0.0829 0.4909 -0.1073 0.040 Uiso 1 1 calc R . . C4 C -0.2892(3) 0.5907(5) -0.06315(9) 0.0315(6) Uani 1 1 d . . . C5 C -0.4332(4) 0.4574(5) -0.09760(11) 0.0399(7) Uani 1 1 d . . . H5A H -0.5367 0.4140 -0.0787 0.060 Uiso 1 1 calc R . . H5B H -0.3777 0.3140 -0.1101 0.060 Uiso 1 1 calc R . . H5C H -0.4784 0.5581 -0.1263 0.060 Uiso 1 1 calc R . . C6 C -0.3743(4) 0.8096(5) -0.04222(11) 0.0412(7) Uani 1 1 d . . . H6A H -0.4644 0.7625 -0.0192 0.062 Uiso 1 1 calc R . . H6B H -0.4366 0.9024 -0.0702 0.062 Uiso 1 1 calc R . . H6C H -0.2770 0.9053 -0.0238 0.062 Uiso 1 1 calc R . . C7 C 0.0399(3) 0.8413(4) -0.17015(9) 0.0297(6) Uani 1 1 d . . . C8 C 0.1747(4) 1.0151(5) -0.16304(10) 0.0362(6) Uani 1 1 d . . . H8 H 0.1588 1.1446 -0.1412 0.043 Uiso 1 1 calc R . . C9 C 0.3327(4) 1.0002(5) -0.18781(10) 0.0399(7) Uani 1 1 d . . . H9 H 0.4247 1.1195 -0.1829 0.048 Uiso 1 1 calc R . . C10 C 0.3563(3) 0.8126(5) -0.21944(10) 0.0393(7) Uani 1 1 d . . . H10 H 0.4647 0.8029 -0.2364 0.047 Uiso 1 1 calc R . . C11 C 0.2232(3) 0.6383(5) -0.22671(10) 0.0368(6) Uani 1 1 d . . . H11 H 0.2403 0.5083 -0.2483 0.044 Uiso 1 1 calc R . . C12 C 0.0645(3) 0.6541(5) -0.20231(9) 0.0330(6) Uani 1 1 d . . . H12 H -0.0281 0.5357 -0.2077 0.040 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 0.0322(4) 0.0500(5) 0.0389(4) 0.0118(3) 0.0128(3) 0.0108(3) O1 0.0268(9) 0.0482(12) 0.0355(10) 0.0064(9) 0.0005(7) -0.0039(8) C1 0.0262(13) 0.0393(15) 0.0355(14) -0.0030(12) 0.0043(10) -0.0022(11) C2 0.0333(14) 0.0418(16) 0.0358(14) 0.0072(12) 0.0072(11) -0.0051(12) C3 0.0292(13) 0.0397(15) 0.0308(13) 0.0034(11) 0.0062(10) 0.0005(11) C4 0.0269(12) 0.0349(14) 0.0331(13) 0.0035(11) 0.0051(10) -0.0021(10) C5 0.0345(14) 0.0399(16) 0.0443(16) 0.0029(13) -0.0003(11) -0.0043(12) C6 0.0375(15) 0.0415(17) 0.0473(16) -0.0034(13) 0.0164(12) -0.0045(12) C7 0.0276(13) 0.0371(15) 0.0245(12) 0.0055(11) 0.0036(9) 0.0045(11) C8 0.0424(15) 0.0342(15) 0.0319(13) -0.0026(11) 0.0037(11) 0.0003(12) C9 0.0352(15) 0.0416(17) 0.0429(15) 0.0010(13) 0.0049(12) -0.0116(12) C10 0.0271(14) 0.0561(19) 0.0357(14) 0.0020(13) 0.0073(11) -0.0008(12) C11 0.0344(14) 0.0422(16) 0.0338(14) -0.0069(12) 0.0036(11) 0.0048(12) C12 0.0273(13) 0.0356(14) 0.0356(14) 0.0010(12) 0.0005(10) -0.0035(11) _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 1.775(2) . ? S1 C3 1.833(3) . ? O1 C1 1.413(3) . ? O1 C4 1.463(3) 3_565 ? C1 C1 1.501(5) 3_565 ? C1 C2 1.525(4) . ? C1 H1 1.0000 . ? C2 C3 1.520(3) . ? C2 H2A 0.9900 . ? C2 H2B 0.9900 . ? C3 C4 1.551(3) . ? C3 H3 1.0000 . ? C4 O1 1.463(3) 3_565 ? C4 C5 1.516(4) . ? C4 C6 1.516(4) . ? C5 H5A 0.9800 . ? C5 H5B 0.9800 . ? C5 H5C 0.9800 . ? C6 H6A 0.9800 . ? C6 H6B 0.9800 . ? C6 H6C 0.9800 . ? C7 C12 1.384(4) . ? C7 C8 1.387(4) . ? C8 C9 1.386(4) . ? C8 H8 0.9500 . ? C9 C10 1.376(4) . ? C9 H9 0.9500 . ? C10 C11 1.381(4) . ? C10 H10 0.9500 . ? C11 C12 1.386(4) . ? C11 H11 0.9500 . ? C12 H12 0.9500 . ? 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 C3 99.57(11) . . ? C1 O1 C4 116.17(19) . 3_565 ? O1 C1 C1 110.6(3) . 3_565 ? O1 C1 C2 110.2(2) . . ? C1 C1 C2 108.9(3) 3_565 . ? O1 C1 H1 109.0 . . ? C1 C1 H1 109.0 3_565 . ? C2 C1 H1 109.0 . . ? C3 C2 C1 109.8(2) . . ? C3 C2 H2A 109.7 . . ? C1 C2 H2A 109.7 . . ? C3 C2 H2B 109.7 . . ? C1 C2 H2B 109.7 . . ? H2A C2 H2B 108.2 . . ? C2 C3 C4 112.9(2) . . ? C2 C3 S1 111.92(18) . . ? C4 C3 S1 110.14(17) . . ? C2 C3 H3 107.2 . . ? C4 C3 H3 107.2 . . ? S1 C3 H3 107.2 . . ? O1 C4 C5 102.8(2) 3_565 . ? O1 C4 C6 111.2(2) 3_565 . ? C5 C4 C6 110.2(2) . . ? O1 C4 C3 106.80(19) 3_565 . ? C5 C4 C3 111.2(2) . . ? C6 C4 C3 114.1(2) . . ? C4 C5 H5A 109.5 . . ? C4 C5 H5B 109.5 . . ? H5A C5 H5B 109.5 . . ? C4 C5 H5C 109.5 . . ? H5A C5 H5C 109.5 . . ? H5B C5 H5C 109.5 . . ? C4 C6 H6A 109.5 . . ? C4 C6 H6B 109.5 . . ? H6A C6 H6B 109.5 . . ? C4 C6 H6C 109.5 . . ? H6A C6 H6C 109.5 . . ? H6B C6 H6C 109.5 . . ? C12 C7 C8 119.4(2) . . ? C12 C7 S1 120.82(19) . . ? C8 C7 S1 119.80(19) . . ? C9 C8 C7 120.1(2) . . ? C9 C8 H8 119.9 . . ? C7 C8 H8 119.9 . . ? C10 C9 C8 120.1(2) . . ? C10 C9 H9 120.0 . . ? C8 C9 H9 120.0 . . ? C9 C10 C11 120.3(2) . . ? C9 C10 H10 119.8 . . ? C11 C10 H10 119.8 . . ? C10 C11 C12 119.7(2) . . ? C10 C11 H11 120.2 . . ? C12 C11 H11 120.2 . . ? C7 C12 C11 120.5(2) . . ? C7 C12 H12 119.8 . . ? C11 C12 H12 119.8 . . ? 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 C4 O1 C1 C1 62.2(3) 3_565 . . 3_565 ? C4 O1 C1 C2 -177.34(19) 3_565 . . . ? O1 C1 C2 C3 -177.1(2) . . . . ? C1 C1 C2 C3 -55.6(3) 3_565 . . . ? C1 C2 C3 C4 54.1(3) . . . . ? C1 C2 C3 S1 179.03(17) . . . . ? C7 S1 C3 C2 64.2(2) . . . . ? C7 S1 C3 C4 -169.30(18) . . . . ? C2 C3 C4 O1 -51.5(3) . . . 3_565 ? S1 C3 C4 O1 -177.43(16) . . . 3_565 ? C2 C3 C4 C5 -162.9(2) . . . . ? S1 C3 C4 C5 71.1(2) . . . . ? C2 C3 C4 C6 71.8(3) . . . . ? S1 C3 C4 C6 -54.2(3) . . . . ? C3 S1 C7 C12 76.2(2) . . . . ? C3 S1 C7 C8 -105.4(2) . . . . ? C12 C7 C8 C9 -0.3(4) . . . . ? S1 C7 C8 C9 -178.7(2) . . . . ? C7 C8 C9 C10 -0.1(4) . . . . ? C8 C9 C10 C11 0.0(4) . . . . ? C9 C10 C11 C12 0.6(4) . . . . ? C8 C7 C12 C11 0.9(4) . . . . ? S1 C7 C12 C11 179.28(19) . . . . ? C10 C11 C12 C7 -1.0(4) . . . . ? _diffrn_measured_fraction_theta_max 0.970 _diffrn_reflns_theta_full 25.03 _diffrn_measured_fraction_theta_full 0.970 _refine_diff_density_max 0.434 _refine_diff_density_min -0.258 _refine_diff_density_rms 0.054 data_sw0209 _database_code_CSD 216121 _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C24 H30 O2 S2' _chemical_formula_sum 'C24 H30 O2 S2' _chemical_formula_weight 414.60 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 Monoclinic _symmetry_space_group_name_H-M P2(1) loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z' _cell_length_a 9.7835(3) _cell_length_b 11.2223(4) _cell_length_c 10.6280(3) _cell_angle_alpha 90.00 _cell_angle_beta 109.981(2) _cell_angle_gamma 90.00 _cell_volume 1096.64(6) _cell_formula_units_Z 2 _cell_measurement_temperature 180(2) _cell_measurement_reflns_used 4869 _cell_measurement_theta_min 1.00 _cell_measurement_theta_max 27.48 _exptl_crystal_description ? _exptl_crystal_colour ? _exptl_crystal_size_max 0.23 _exptl_crystal_size_mid 0.18 _exptl_crystal_size_min 0.12 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.256 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 444 _exptl_absorpt_coefficient_mu 0.260 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.932 _exptl_absorpt_correction_T_max 0.970 _exptl_absorpt_process_details ; multi-scan from symmetry-related measurements Sortav (Blessing 1995) ; _exptl_special_details ; ? ; _diffrn_ambient_temperature 180(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_measurement_device_type 'Nonius Kappa CCD' _diffrn_measurement_method 'Thin slice \w and \f scans' _diffrn_standards_number 0 _diffrn_reflns_number 6935 _diffrn_reflns_av_R_equivalents 0.0409 _diffrn_reflns_av_sigmaI/netI 0.0661 _diffrn_reflns_limit_h_min -12 _diffrn_reflns_limit_h_max 11 _diffrn_reflns_limit_k_min -14 _diffrn_reflns_limit_k_max 13 _diffrn_reflns_limit_l_min -13 _diffrn_reflns_limit_l_max 13 _diffrn_reflns_theta_min 3.92 _diffrn_reflns_theta_max 27.48 _reflns_number_total 4285 _reflns_number_gt 3679 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Collect (Nonius B.V. 1998)' _computing_cell_refinement 'HKL Scalepack (Otwinowski & Minor 1997)' _computing_data_reduction ; HKL Denzo and Scalepack (Otwinowski & Minor 1997) ; _computing_structure_solution 'SIR-92 (Altomare et al. 1994)' _computing_structure_refinement 'SHELXL-97 (Sheldrick 1997)' _computing_publication_material 'SHELXL-97 (Sheldrick 1997)' _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^)+(0.0166P)^2^+0.1750P] 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 -0.04(6) _refine_ls_number_reflns 4285 _refine_ls_number_parameters 257 _refine_ls_number_restraints 1 _refine_ls_R_factor_all 0.0535 _refine_ls_R_factor_gt 0.0383 _refine_ls_wR_factor_ref 0.0777 _refine_ls_wR_factor_gt 0.0721 _refine_ls_goodness_of_fit_ref 1.039 _refine_ls_restrained_S_all 1.039 _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 1.04090(6) 0.42040(6) 0.96165(5) 0.03828(16) Uani 1 1 d . . . S2 S 0.45230(6) 0.06436(6) 0.33243(5) 0.04047(17) Uani 1 1 d . . . O1 O 0.85836(15) 0.28282(13) 0.58873(13) 0.0291(3) Uani 1 1 d . . . O2 O 0.65557(15) 0.18369(13) 0.71028(13) 0.0280(3) Uani 1 1 d . . . C1 C 0.9602(2) 0.3515(2) 0.6953(2) 0.0293(5) Uani 1 1 d . . . C2 C 0.9121(2) 0.3410(2) 0.81885(19) 0.0275(5) Uani 1 1 d . . . H2 H 0.8147 0.3798 0.7969 0.033 Uiso 1 1 calc R . . C3 C 0.8981(2) 0.2120(2) 0.8563(2) 0.0312(5) Uani 1 1 d . . . H3A H 0.9957 0.1750 0.8896 0.037 Uiso 1 1 calc R . . H3B H 0.8568 0.2093 0.9292 0.037 Uiso 1 1 calc R . . C4 C 0.8011(2) 0.1417(2) 0.73697(19) 0.0292(5) Uani 1 1 d . . . H4 H 0.8063 0.0552 0.7607 0.035 Uiso 1 1 calc R . . C5 C 0.8489(2) 0.1587(2) 0.6164(2) 0.0294(5) Uani 1 1 d . . . H5 H 0.9460 0.1204 0.6342 0.035 Uiso 1 1 calc R . . C6 C 0.7391(2) 0.1036(2) 0.4926(2) 0.0319(5) Uani 1 1 d . . . H6A H 0.7446 0.0157 0.5008 0.038 Uiso 1 1 calc R . . H6B H 0.7639 0.1261 0.4130 0.038 Uiso 1 1 calc R . . C7 C 0.5845(2) 0.1440(2) 0.47316(19) 0.0284(5) Uani 1 1 d . . . H7 H 0.5773 0.2309 0.4511 0.034 Uiso 1 1 calc R . . C8 C 0.5438(2) 0.1267(2) 0.6000(2) 0.0276(5) Uani 1 1 d . . . C9 C 1.1154(2) 0.3078(2) 0.7205(2) 0.0395(6) Uani 1 1 d . . . H9A H 1.1338 0.3051 0.6355 0.059 Uiso 1 1 calc R . . H9B H 1.1271 0.2278 0.7598 0.059 Uiso 1 1 calc R . . H9C H 1.1845 0.3624 0.7822 0.059 Uiso 1 1 calc R . . C10 C 0.9428(3) 0.4785(2) 0.6429(2) 0.0394(6) Uani 1 1 d . . . H10A H 0.8418 0.5041 0.6232 0.059 Uiso 1 1 calc R . . H10B H 0.9674 0.4821 0.5611 0.059 Uiso 1 1 calc R . . H10C H 1.0078 0.5312 0.7107 0.059 Uiso 1 1 calc R . . C11 C 0.5276(3) -0.0040(2) 0.6316(2) 0.0392(6) Uani 1 1 d . . . H11A H 0.5193 -0.0105 0.7207 0.059 Uiso 1 1 calc R . . H11B H 0.6131 -0.0486 0.6298 0.059 Uiso 1 1 calc R . . H11C H 0.4401 -0.0370 0.5646 0.059 Uiso 1 1 calc R . . C12 C 0.4070(2) 0.1958(2) 0.5912(2) 0.0394(6) Uani 1 1 d . . . H12A H 0.3831 0.1818 0.6723 0.059 Uiso 1 1 calc R . . H12B H 0.3262 0.1690 0.5127 0.059 Uiso 1 1 calc R . . H12C H 0.4237 0.2811 0.5828 0.059 Uiso 1 1 calc R . . C13 C 0.9502(2) 0.4073(2) 1.0803(2) 0.0310(5) Uani 1 1 d . . . C14 C 1.0060(3) 0.3324(2) 1.1907(2) 0.0400(6) Uani 1 1 d . . . H14 H 1.0900 0.2856 1.2006 0.048 Uiso 1 1 calc R . . C15 C 0.9383(3) 0.3263(3) 1.2860(2) 0.0477(7) Uani 1 1 d . . . H15 H 0.9768 0.2757 1.3615 0.057 Uiso 1 1 calc R . . C16 C 0.8164(3) 0.3929(3) 1.2722(2) 0.0478(7) Uani 1 1 d . . . H16 H 0.7710 0.3884 1.3380 0.057 Uiso 1 1 calc R . . C17 C 0.7600(3) 0.4665(2) 1.1625(2) 0.0450(6) Uani 1 1 d . . . H17 H 0.6750 0.5121 1.1522 0.054 Uiso 1 1 calc R . . C18 C 0.8274(2) 0.4739(2) 1.0674(2) 0.0375(5) Uani 1 1 d . . . H18 H 0.7888 0.5252 0.9925 0.045 Uiso 1 1 calc R . . C19 C 0.4893(2) 0.1311(2) 0.1962(2) 0.0302(5) Uani 1 1 d . . . C20 C 0.5868(2) 0.0791(3) 0.1443(2) 0.0413(6) Uani 1 1 d . . . H20 H 0.6356 0.0077 0.1827 0.050 Uiso 1 1 calc R . . C21 C 0.6133(3) 0.1307(3) 0.0369(3) 0.0495(7) Uani 1 1 d . . . H21 H 0.6804 0.0943 0.0019 0.059 Uiso 1 1 calc R . . C22 C 0.5447(3) 0.2328(3) -0.0194(2) 0.0499(7) Uani 1 1 d . . . H22 H 0.5640 0.2678 -0.0930 0.060 Uiso 1 1 calc R . . C23 C 0.4473(3) 0.2850(3) 0.0308(2) 0.0479(7) Uani 1 1 d . . . H23 H 0.3991 0.3563 -0.0085 0.057 Uiso 1 1 calc R . . C24 C 0.4185(2) 0.2348(2) 0.1378(2) 0.0382(6) Uani 1 1 d . . . H24 H 0.3503 0.2713 0.1714 0.046 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 0.0343(3) 0.0496(4) 0.0323(3) -0.0089(3) 0.0131(2) -0.0137(3) S2 0.0411(3) 0.0479(4) 0.0316(3) -0.0061(3) 0.0115(2) -0.0192(3) O1 0.0284(8) 0.0324(9) 0.0272(7) -0.0013(7) 0.0102(6) -0.0046(7) O2 0.0289(8) 0.0311(9) 0.0253(7) -0.0017(6) 0.0110(6) -0.0025(6) C1 0.0231(11) 0.0379(14) 0.0279(11) -0.0012(10) 0.0098(9) -0.0053(10) C2 0.0245(10) 0.0320(13) 0.0258(10) -0.0012(10) 0.0083(8) -0.0022(10) C3 0.0323(11) 0.0334(13) 0.0271(11) 0.0034(10) 0.0092(9) -0.0013(10) C4 0.0296(11) 0.0279(12) 0.0292(11) 0.0026(10) 0.0090(8) 0.0009(9) C5 0.0261(10) 0.0311(12) 0.0314(11) -0.0013(10) 0.0103(8) 0.0026(10) C6 0.0331(11) 0.0351(13) 0.0300(11) -0.0050(10) 0.0140(9) -0.0030(10) C7 0.0283(11) 0.0297(13) 0.0274(11) -0.0012(10) 0.0098(9) -0.0079(10) C8 0.0275(11) 0.0289(12) 0.0284(11) -0.0011(10) 0.0121(9) -0.0033(9) C9 0.0277(12) 0.0537(17) 0.0395(13) -0.0068(12) 0.0146(10) -0.0041(11) C10 0.0449(14) 0.0368(14) 0.0381(13) 0.0007(12) 0.0161(11) -0.0074(12) C11 0.0452(14) 0.0369(14) 0.0386(13) 0.0000(12) 0.0181(11) -0.0095(11) C12 0.0315(12) 0.0486(16) 0.0413(13) -0.0061(12) 0.0167(10) -0.0018(11) C13 0.0327(11) 0.0331(13) 0.0284(11) -0.0089(11) 0.0120(9) -0.0072(11) C14 0.0400(13) 0.0389(14) 0.0392(13) -0.0001(12) 0.0110(11) -0.0006(12) C15 0.0585(17) 0.0533(17) 0.0318(12) 0.0017(13) 0.0160(12) -0.0073(15) C16 0.0475(15) 0.060(2) 0.0423(14) -0.0143(14) 0.0230(12) -0.0113(14) C17 0.0370(13) 0.0534(17) 0.0465(14) -0.0162(14) 0.0167(11) 0.0002(12) C18 0.0357(12) 0.0398(14) 0.0331(12) -0.0039(11) 0.0069(10) -0.0024(11) C19 0.0282(11) 0.0354(13) 0.0254(10) -0.0074(10) 0.0070(8) -0.0061(10) C20 0.0419(13) 0.0413(15) 0.0415(12) -0.0054(13) 0.0153(10) 0.0016(12) C21 0.0552(16) 0.0576(18) 0.0447(14) -0.0148(15) 0.0285(12) -0.0057(15) C22 0.0611(17) 0.0615(19) 0.0276(12) -0.0052(13) 0.0160(12) -0.0223(15) C23 0.0550(16) 0.0450(16) 0.0339(13) 0.0059(12) 0.0026(11) -0.0017(13) C24 0.0344(12) 0.0415(14) 0.0367(12) -0.0057(12) 0.0096(10) 0.0063(11) _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 C13 1.779(2) . ? S1 C2 1.838(2) . ? S2 C19 1.774(2) . ? S2 C7 1.840(2) . ? O1 C5 1.433(3) . ? O1 C1 1.449(2) . ? O2 C4 1.433(2) . ? O2 C8 1.450(2) . ? C1 C10 1.518(3) . ? C1 C9 1.529(3) . ? C1 C2 1.543(3) . ? C2 C3 1.520(3) . ? C2 H2 1.0000 . ? C3 C4 1.519(3) . ? C3 H3A 0.9900 . ? C3 H3B 0.9900 . ? C4 C5 1.519(3) . ? C4 H4 1.0000 . ? C5 C6 1.518(3) . ? C5 H5 1.0000 . ? C6 C7 1.524(3) . ? C6 H6A 0.9900 . ? C6 H6B 0.9900 . ? C7 C8 1.543(3) . ? C7 H7 1.0000 . ? C8 C12 1.521(3) . ? C8 C11 1.525(3) . ? C9 H9A 0.9800 . ? C9 H9B 0.9800 . ? C9 H9C 0.9800 . ? C10 H10A 0.9800 . ? C10 H10B 0.9800 . ? C10 H10C 0.9800 . ? C11 H11A 0.9800 . ? C11 H11B 0.9800 . ? C11 H11C 0.9800 . ? C12 H12A 0.9800 . ? C12 H12B 0.9800 . ? C12 H12C 0.9800 . ? C13 C18 1.381(3) . ? C13 C14 1.394(3) . ? C14 C15 1.389(3) . ? C14 H14 0.9500 . ? C15 C16 1.372(4) . ? C15 H15 0.9500 . ? C16 C17 1.381(4) . ? C16 H16 0.9500 . ? C17 C18 1.385(3) . ? C17 H17 0.9500 . ? C18 H18 0.9500 . ? C19 C20 1.383(3) . ? C19 C24 1.387(3) . ? C20 C21 1.382(3) . ? C20 H20 0.9500 . ? C21 C22 1.359(4) . ? C21 H21 0.9500 . ? C22 C23 1.372(4) . ? C22 H22 0.9500 . ? C23 C24 1.382(3) . ? C23 H23 0.9500 . ? C24 H24 0.9500 . ? 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 C13 S1 C2 100.25(10) . . ? C19 S2 C7 100.11(10) . . ? C5 O1 C1 115.56(15) . . ? C4 O2 C8 116.05(15) . . ? O1 C1 C10 104.55(17) . . ? O1 C1 C9 110.01(17) . . ? C10 C1 C9 110.2(2) . . ? O1 C1 C2 107.24(16) . . ? C10 C1 C2 110.77(18) . . ? C9 C1 C2 113.60(18) . . ? C3 C2 C1 112.08(17) . . ? C3 C2 S1 110.07(14) . . ? C1 C2 S1 110.06(14) . . ? C3 C2 H2 108.2 . . ? C1 C2 H2 108.2 . . ? S1 C2 H2 108.2 . . ? C4 C3 C2 111.27(17) . . ? C4 C3 H3A 109.4 . . ? C2 C3 H3A 109.4 . . ? C4 C3 H3B 109.4 . . ? C2 C3 H3B 109.4 . . ? H3A C3 H3B 108.0 . . ? O2 C4 C3 106.84(17) . . ? O2 C4 C5 111.32(16) . . ? C3 C4 C5 110.73(17) . . ? O2 C4 H4 109.3 . . ? C3 C4 H4 109.3 . . ? C5 C4 H4 109.3 . . ? O1 C5 C6 107.12(17) . . ? O1 C5 C4 110.82(17) . . ? C6 C5 C4 110.44(17) . . ? O1 C5 H5 109.5 . . ? C6 C5 H5 109.5 . . ? C4 C5 H5 109.5 . . ? C5 C6 C7 111.84(17) . . ? C5 C6 H6A 109.2 . . ? C7 C6 H6A 109.2 . . ? C5 C6 H6B 109.2 . . ? C7 C6 H6B 109.2 . . ? H6A C6 H6B 107.9 . . ? C6 C7 C8 112.61(16) . . ? C6 C7 S2 110.79(15) . . ? C8 C7 S2 109.22(14) . . ? C6 C7 H7 108.0 . . ? C8 C7 H7 108.0 . . ? S2 C7 H7 108.0 . . ? O2 C8 C12 103.27(17) . . ? O2 C8 C11 110.62(19) . . ? C12 C8 C11 110.4(2) . . ? O2 C8 C7 107.58(16) . . ? C12 C8 C7 111.48(18) . . ? C11 C8 C7 113.01(18) . . ? C1 C9 H9A 109.5 . . ? C1 C9 H9B 109.5 . . ? H9A C9 H9B 109.5 . . ? C1 C9 H9C 109.5 . . ? H9A C9 H9C 109.5 . . ? H9B C9 H9C 109.5 . . ? C1 C10 H10A 109.5 . . ? C1 C10 H10B 109.5 . . ? H10A C10 H10B 109.5 . . ? C1 C10 H10C 109.5 . . ? H10A C10 H10C 109.5 . . ? H10B C10 H10C 109.5 . . ? C8 C11 H11A 109.5 . . ? C8 C11 H11B 109.5 . . ? H11A C11 H11B 109.5 . . ? C8 C11 H11C 109.5 . . ? H11A C11 H11C 109.5 . . ? H11B C11 H11C 109.5 . . ? C8 C12 H12A 109.5 . . ? C8 C12 H12B 109.5 . . ? H12A C12 H12B 109.5 . . ? C8 C12 H12C 109.5 . . ? H12A C12 H12C 109.5 . . ? H12B C12 H12C 109.5 . . ? C18 C13 C14 119.2(2) . . ? C18 C13 S1 120.81(18) . . ? C14 C13 S1 119.96(17) . . ? C15 C14 C13 119.7(2) . . ? C15 C14 H14 120.1 . . ? C13 C14 H14 120.1 . . ? C16 C15 C14 120.6(3) . . ? C16 C15 H15 119.7 . . ? C14 C15 H15 119.7 . . ? C15 C16 C17 119.9(2) . . ? C15 C16 H16 120.1 . . ? C17 C16 H16 120.1 . . ? C16 C17 C18 119.9(2) . . ? C16 C17 H17 120.0 . . ? C18 C17 H17 120.0 . . ? C13 C18 C17 120.6(2) . . ? C13 C18 H18 119.7 . . ? C17 C18 H18 119.7 . . ? C20 C19 C24 118.9(2) . . ? C20 C19 S2 120.48(19) . . ? C24 C19 S2 120.60(17) . . ? C21 C20 C19 120.1(3) . . ? C21 C20 H20 119.9 . . ? C19 C20 H20 119.9 . . ? C22 C21 C20 120.9(2) . . ? C22 C21 H21 119.6 . . ? C20 C21 H21 119.6 . . ? C21 C22 C23 119.5(2) . . ? C21 C22 H22 120.2 . . ? C23 C22 H22 120.2 . . ? C22 C23 C24 120.7(3) . . ? C22 C23 H23 119.7 . . ? C24 C23 H23 119.7 . . ? C23 C24 C19 119.9(2) . . ? C23 C24 H24 120.1 . . ? C19 C24 H24 120.1 . . ? 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 C5 O1 C1 C10 -177.22(17) . . . . ? C5 O1 C1 C9 64.4(2) . . . . ? C5 O1 C1 C2 -59.6(2) . . . . ? O1 C1 C2 C3 54.6(2) . . . . ? C10 C1 C2 C3 168.10(18) . . . . ? C9 C1 C2 C3 -67.2(2) . . . . ? O1 C1 C2 S1 177.43(14) . . . . ? C10 C1 C2 S1 -69.1(2) . . . . ? C9 C1 C2 S1 55.7(2) . . . . ? C13 S1 C2 C3 -61.81(17) . . . . ? C13 S1 C2 C1 174.17(15) . . . . ? C1 C2 C3 C4 -52.9(2) . . . . ? S1 C2 C3 C4 -175.70(14) . . . . ? C8 O2 C4 C3 -179.22(16) . . . . ? C8 O2 C4 C5 59.8(2) . . . . ? C2 C3 C4 O2 -70.5(2) . . . . ? C2 C3 C4 C5 50.9(2) . . . . ? C1 O1 C5 C6 -179.21(16) . . . . ? C1 O1 C5 C4 60.3(2) . . . . ? O2 C4 C5 O1 65.6(2) . . . . ? C3 C4 C5 O1 -53.1(2) . . . . ? O2 C4 C5 C6 -53.0(2) . . . . ? C3 C4 C5 C6 -171.67(18) . . . . ? O1 C5 C6 C7 -70.5(2) . . . . ? C4 C5 C6 C7 50.3(2) . . . . ? C5 C6 C7 C8 -51.7(3) . . . . ? C5 C6 C7 S2 -174.33(15) . . . . ? C19 S2 C7 C6 -71.27(17) . . . . ? C19 S2 C7 C8 164.12(15) . . . . ? C4 O2 C8 C12 -175.98(17) . . . . ? C4 O2 C8 C11 65.9(2) . . . . ? C4 O2 C8 C7 -58.0(2) . . . . ? C6 C7 C8 O2 52.6(2) . . . . ? S2 C7 C8 O2 176.18(14) . . . . ? C6 C7 C8 C12 165.19(18) . . . . ? S2 C7 C8 C12 -71.3(2) . . . . ? C6 C7 C8 C11 -69.8(2) . . . . ? S2 C7 C8 C11 53.8(2) . . . . ? C2 S1 C13 C18 -73.6(2) . . . . ? C2 S1 C13 C14 108.78(19) . . . . ? C18 C13 C14 C15 -0.5(3) . . . . ? S1 C13 C14 C15 177.24(19) . . . . ? C13 C14 C15 C16 0.4(4) . . . . ? C14 C15 C16 C17 0.1(4) . . . . ? C15 C16 C17 C18 -0.7(4) . . . . ? C14 C13 C18 C17 -0.1(3) . . . . ? S1 C13 C18 C17 -177.74(18) . . . . ? C16 C17 C18 C13 0.6(4) . . . . ? C7 S2 C19 C20 93.44(19) . . . . ? C7 S2 C19 C24 -88.06(19) . . . . ? C24 C19 C20 C21 0.5(3) . . . . ? S2 C19 C20 C21 179.01(19) . . . . ? C19 C20 C21 C22 0.0(4) . . . . ? C20 C21 C22 C23 -0.3(4) . . . . ? C21 C22 C23 C24 0.1(4) . . . . ? C22 C23 C24 C19 0.5(4) . . . . ? C20 C19 C24 C23 -0.7(3) . . . . ? S2 C19 C24 C23 -179.25(18) . . . . ? _diffrn_measured_fraction_theta_max 0.992 _diffrn_reflns_theta_full 27.48 _diffrn_measured_fraction_theta_full 0.992 _refine_diff_density_max 0.201 _refine_diff_density_min -0.208 _refine_diff_density_rms 0.044