# Supplementary Material (ESI) for Organic & Biomolecular Chemistry # This journal is © The Royal Society of Chemistry 2004 data_global _publ_contact_author_email RICHARD.GRAINGER@KCL.AC.UK _publ_contact_author_name 'Dr Richard Grainger' _journal_name_full Org.Biomol.Chem. _journal_coden_Cambridge 0177 _publ_contact_author_address ; Chemistry King's College London Strand London WC2R 2LS UNITED KINGDOM ; _publ_section_title ; Diastereotopic group selective intramolecular cycloadditions of sulfenic acids to 1,4-dienes ; loop_ _publ_author_name 'Richard Grainger' 'Jonathan W. Steed' 'Patrizia Tisselli' data_PT1062B.CIF _database_code_depnum_ccdc_archive 'CCDC 218529' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C9 H14 O2 S' _chemical_formula_weight 186.26 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 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 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 7.5780(3) _cell_length_b 9.7836(4) _cell_length_c 12.0885(5) _cell_angle_alpha 90.00 _cell_angle_beta 92.028(2) _cell_angle_gamma 90.00 _cell_volume 895.68(6) _cell_formula_units_Z 4 _cell_measurement_temperature 120(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description ? _exptl_crystal_colour ? _exptl_crystal_size_max 0.20 _exptl_crystal_size_mid 0.15 _exptl_crystal_size_min 0.10 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.381 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 400 _exptl_absorpt_coefficient_mu 0.317 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.9394 _exptl_absorpt_correction_T_max 0.9690 _exptl_absorpt_process_details ? _exptl_special_details ; Data were corrected for decay and absorption using the program Scalepack based on the method of Otwinowski & Minor, 1997. ; _diffrn_ambient_temperature 120(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 'Nonis KappaCCD CCD diffractometer' _diffrn_measurement_method 'phi & omega scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% 0.0 _diffrn_reflns_number 2782 _diffrn_reflns_av_R_equivalents 0.0388 _diffrn_reflns_av_sigmaI/netI 0.0622 _diffrn_reflns_limit_h_min -9 _diffrn_reflns_limit_h_max 9 _diffrn_reflns_limit_k_min -12 _diffrn_reflns_limit_k_max 12 _diffrn_reflns_limit_l_min -14 _diffrn_reflns_limit_l_max 14 _diffrn_reflns_theta_min 3.12 _diffrn_reflns_theta_max 27.46 _reflns_number_total 1640 _reflns_number_gt 1265 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Collect (Nonius, 1998)' _computing_cell_refinement 'DENZO-SMN (Otwinowski & Minor, 1997)' _computing_data_reduction 'DENZO-SMN (Otwinowski & Minor, 1997)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'X-Seed (Barbour, 1999)' _computing_publication_material 'CIFTAB (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^)+(0.0289P)^2^+0.1969P] 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 SHELXL _refine_ls_extinction_coef 0.010(3) _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_number_reflns 1640 _refine_ls_number_parameters 115 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0560 _refine_ls_R_factor_gt 0.0361 _refine_ls_wR_factor_ref 0.0839 _refine_ls_wR_factor_gt 0.0779 _refine_ls_goodness_of_fit_ref 1.069 _refine_ls_restrained_S_all 1.069 _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 -0.01549(7) 0.34988(5) 0.41795(4) 0.0187(2) Uani 1 1 d . . . O1 O 0.03762(17) 0.28047(13) 0.52580(10) 0.0216(4) Uani 1 1 d . . . C1 C -0.2144(3) 0.2651(2) 0.36601(15) 0.0202(5) Uani 1 1 d . . . H1A H -0.2396 0.1844 0.4123 0.024 Uiso 1 1 calc R . . H1B H -0.3162 0.3283 0.3682 0.024 Uiso 1 1 calc R . . O2 O -0.31035(18) 0.11913(15) 0.21473(12) 0.0236(4) Uani 1 1 d . . . C2 C -0.1845(2) 0.2208(2) 0.24687(15) 0.0166(5) Uani 1 1 d . . . H2 H -0.1986 0.3016 0.1967 0.020 Uiso 1 1 calc R . . C3 C 0.0071(2) 0.1692(2) 0.24474(14) 0.0148(5) Uani 1 1 d . . . C4 C 0.0262(3) 0.0349(2) 0.30495(14) 0.0170(5) Uani 1 1 d . . . H4 H -0.0600 -0.0336 0.2895 0.020 Uiso 1 1 calc R . . C5 C 0.1554(3) 0.0061(2) 0.37803(15) 0.0201(5) Uani 1 1 d . . . H5 H 0.1560 -0.0822 0.4107 0.024 Uiso 1 1 calc R . . C6 C 0.2996(3) 0.1022(2) 0.41256(16) 0.0240(5) Uani 1 1 d . . . H6A H 0.4146 0.0559 0.4047 0.029 Uiso 1 1 calc R . . H6B H 0.2880 0.1250 0.4918 0.029 Uiso 1 1 calc R . . C7 C 0.2988(3) 0.2345(2) 0.34552(17) 0.0226(5) Uani 1 1 d . . . H7A H 0.3523 0.3080 0.3919 0.027 Uiso 1 1 calc R . . H7B H 0.3736 0.2218 0.2808 0.027 Uiso 1 1 calc R . . C8 C 0.1153(2) 0.2799(2) 0.30469(15) 0.0164(5) Uani 1 1 d . . . H8 H 0.1319 0.3557 0.2505 0.020 Uiso 1 1 calc R . . C9 C 0.0620(3) 0.1525(2) 0.12393(15) 0.0236(5) Uani 1 1 d . . . H9A H 0.1856 0.1231 0.1229 0.035 Uiso 1 1 calc R . . H9B H 0.0486 0.2400 0.0852 0.035 Uiso 1 1 calc R . . H9C H -0.0132 0.0837 0.0869 0.035 Uiso 1 1 calc R . . H1 H -0.355(3) 0.146(2) 0.149(2) 0.047(8) Uiso 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 S1 0.0230(3) 0.0168(3) 0.0158(3) -0.0019(2) -0.0051(2) 0.0021(2) O1 0.0272(9) 0.0232(8) 0.0138(7) 0.0010(6) -0.0078(6) 0.0028(6) C1 0.0148(11) 0.0278(13) 0.0179(11) -0.0015(9) -0.0030(8) 0.0036(9) O2 0.0199(9) 0.0318(9) 0.0184(8) 0.0022(7) -0.0090(6) -0.0071(7) C2 0.0166(11) 0.0194(12) 0.0134(10) 0.0011(8) -0.0035(8) -0.0013(9) C3 0.0137(11) 0.0192(11) 0.0115(10) 0.0002(8) -0.0010(8) -0.0002(9) C4 0.0198(11) 0.0150(11) 0.0162(10) -0.0037(9) 0.0013(8) -0.0010(9) C5 0.0260(12) 0.0150(11) 0.0192(11) 0.0015(9) 0.0019(9) 0.0048(9) C6 0.0181(12) 0.0269(12) 0.0265(12) -0.0020(10) -0.0053(9) 0.0075(10) C7 0.0159(12) 0.0257(12) 0.0261(11) -0.0012(10) -0.0013(9) -0.0037(10) C8 0.0163(11) 0.0186(12) 0.0143(10) 0.0035(9) -0.0013(8) -0.0014(9) C9 0.0244(12) 0.0296(13) 0.0169(11) -0.0012(10) 0.0028(9) 0.0020(10) _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 O1 1.5119(13) . ? S1 C1 1.813(2) . ? S1 C8 1.8497(19) . ? C1 C2 1.529(3) . ? O2 C2 1.423(2) . ? C2 C3 1.538(3) . ? C3 C4 1.506(3) . ? C3 C8 1.526(3) . ? C3 C9 1.541(2) . ? C4 C5 1.325(3) . ? C5 C6 1.490(3) . ? C6 C7 1.527(3) . ? C7 C8 1.525(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 O1 S1 C1 106.61(8) . . ? O1 S1 C8 109.80(8) . . ? C1 S1 C8 92.00(8) . . ? C2 C1 S1 107.88(13) . . ? O2 C2 C1 109.60(16) . . ? O2 C2 C3 112.94(16) . . ? C1 C2 C3 106.28(15) . . ? C4 C3 C8 110.40(15) . . ? C4 C3 C2 110.69(16) . . ? C8 C3 C2 104.50(15) . . ? C4 C3 C9 109.93(15) . . ? C8 C3 C9 111.49(16) . . ? C2 C3 C9 109.73(15) . . ? C5 C4 C3 124.36(18) . . ? C4 C5 C6 124.68(19) . . ? C5 C6 C7 113.41(16) . . ? C8 C7 C6 113.90(17) . . ? C7 C8 C3 114.53(16) . . ? C7 C8 S1 112.00(13) . . ? C3 C8 S1 108.74(13) . . ? loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA _geom_hbond_site_symmetry_A O2 H1 O1 0.90(2) 1.82(2) 2.7059(19) 172(2) 4_565 _diffrn_measured_fraction_theta_max 0.798 _diffrn_reflns_theta_full 27.46 _diffrn_measured_fraction_theta_full 0.798 _refine_diff_density_max 0.262 _refine_diff_density_min -0.281 _refine_diff_density_rms 0.057 data_PT062A.CIF _database_code_depnum_ccdc_archive 'CCDC 218530' _chemical_name_common pt062a _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C9 H15 O2.50 S' _chemical_formula_weight 195.27 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting triclinic _symmetry_space_group_name_H-M P-1 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 7.1304(3) _cell_length_b 10.9979(4) _cell_length_c 13.4699(6) _cell_angle_alpha 109.079(2) _cell_angle_beta 92.0540(10) _cell_angle_gamma 100.681(2) _cell_volume 975.68(7) _cell_formula_units_Z 4 _cell_measurement_temperature 120(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description prism _exptl_crystal_colour colourless _exptl_crystal_size_max 0.80 _exptl_crystal_size_mid 0.25 _exptl_crystal_size_min 0.20 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.329 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 420 _exptl_absorpt_coefficient_mu 0.298 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.7967 _exptl_absorpt_correction_T_max 0.9429 _exptl_absorpt_process_details ? _exptl_special_details ; Data were corrected for decay and absorption using the program Scalepack Z. Otwinowski and W. Minor, in Methods in Enzymology, ed. C. W. Carter and R. M. Sweet, Academic Press: London, 1997, vol. 276, pp 307. ; _diffrn_ambient_temperature 120(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 'Nonius KappaCCD' _diffrn_measurement_method ? _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% 0.0 _diffrn_reflns_number 3808 _diffrn_reflns_av_R_equivalents 0.0534 _diffrn_reflns_av_sigmaI/netI 0.0614 _diffrn_reflns_limit_h_min -7 _diffrn_reflns_limit_h_max 9 _diffrn_reflns_limit_k_min -13 _diffrn_reflns_limit_k_max 11 _diffrn_reflns_limit_l_min -16 _diffrn_reflns_limit_l_max 17 _diffrn_reflns_theta_min 2.92 _diffrn_reflns_theta_max 27.44 _reflns_number_total 2637 _reflns_number_gt 2203 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Collect (Hooft, 1999)' _computing_cell_refinement 'DENZO-SMN (Otwinowski & Minor, 1997)' _computing_data_reduction 'DENZO-SMN (Otwinowski & Minor, 1997)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'X-Seed (Barbour, 1999)' _computing_publication_material 'CIFTAB (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^)+(0.0251P)^2^+0.6204P] 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 SHELXL _refine_ls_extinction_coef 0.014(3) _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_number_reflns 2637 _refine_ls_number_parameters 239 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0475 _refine_ls_R_factor_gt 0.0347 _refine_ls_wR_factor_ref 0.0892 _refine_ls_wR_factor_gt 0.0832 _refine_ls_goodness_of_fit_ref 1.047 _refine_ls_restrained_S_all 1.047 _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 -0.83177(9) 0.37586(6) 0.10753(5) 0.0222(2) Uani 1 1 d . . . O1 O -0.9108(3) 0.29673(17) 0.17595(13) 0.0322(5) Uani 1 1 d . . . C1 C -0.9910(3) 0.3157(2) -0.01356(19) 0.0216(6) Uani 1 1 d . . . H1A H -1.0677 0.2269 -0.0240 0.026 Uiso 1 1 calc R . . H1B H -1.0793 0.3757 -0.0125 0.026 Uiso 1 1 calc R . . S2 S -0.35704(9) 0.37045(6) -0.47332(5) 0.0213(2) Uani 1 1 d . . . O2 O -0.7830(2) 0.44450(15) -0.08955(13) 0.0220(4) Uani 1 1 d . . . H2 H -0.7384 0.4475 -0.1458 0.026 Uiso 1 1 calc R . . C2 C -0.8594(3) 0.3116(2) -0.10013(19) 0.0185(6) Uani 1 1 d . . . H2A H -0.9318 0.2628 -0.1713 0.022 Uiso 1 1 calc R . . H51 H -0.595(4) 0.420(3) -0.313(2) 0.050(10) Uiso 1 1 d . . . O3 O -0.4976(2) 0.30450(16) -0.41558(13) 0.0271(4) Uani 1 1 d . . . C3 C -0.7028(3) 0.2410(2) -0.07881(17) 0.0160(5) Uani 1 1 d . . . O4 O -0.1361(2) 0.37481(14) -0.67030(12) 0.0191(4) Uani 1 1 d . . . H4 H -0.0605 0.3586 -0.7171 0.023 Uiso 1 1 calc R . . C4 C -0.7925(3) 0.0967(2) -0.10462(19) 0.0174(5) Uani 1 1 d . . . H4A H -0.8611 0.0516 -0.1725 0.021 Uiso 1 1 calc R . . O5 O -0.6376(3) 0.47915(19) -0.25952(14) 0.0240(4) Uani 1 1 d . . . C5 C -0.7835(3) 0.0284(2) -0.04073(19) 0.0206(6) Uani 1 1 d . . . H5 H -0.8440 -0.0622 -0.0661 0.025 Uiso 1 1 calc R . . C6 C -0.6839(4) 0.0849(2) 0.0689(2) 0.0249(6) Uani 1 1 d . . . H6A H -0.6063 0.0237 0.0801 0.030 Uiso 1 1 calc R . . H6B H -0.7812 0.0931 0.1200 0.030 Uiso 1 1 calc R . . C7 C -0.5536(4) 0.2195(2) 0.09034(19) 0.0226(6) Uani 1 1 d . . . H7A H -0.5304 0.2656 0.1676 0.027 Uiso 1 1 calc R . . H7B H -0.4283 0.2066 0.0641 0.027 Uiso 1 1 calc R . . C8 C -0.6336(3) 0.3071(2) 0.03946(18) 0.0179(6) Uani 1 1 d . . . H8 H -0.5268 0.3834 0.0462 0.022 Uiso 1 1 calc R . . C9 C -0.5366(3) 0.2547(2) -0.14665(19) 0.0227(6) Uani 1 1 d . . . H9A H -0.5860 0.2181 -0.2215 0.034 Uiso 1 1 calc R . . H9B H -0.4412 0.2068 -0.1329 0.034 Uiso 1 1 calc R . . H9C H -0.4765 0.3479 -0.1287 0.034 Uiso 1 1 calc R . . C10 C -0.4185(3) 0.2779(2) -0.61278(18) 0.0198(6) Uani 1 1 d . . . H10A H -0.5069 0.1931 -0.6227 0.024 Uiso 1 1 calc R . . H10B H -0.4825 0.3282 -0.6475 0.024 Uiso 1 1 calc R . . C11 C -0.2335(3) 0.2543(2) -0.65984(19) 0.0167(5) Uani 1 1 d . . . H11 H -0.2606 0.1824 -0.7302 0.020 Uiso 1 1 calc R . . C12 C -0.1181(3) 0.2140(2) -0.58035(18) 0.0154(5) Uani 1 1 d . . . C13 C -0.2143(3) 0.0779(2) -0.58509(19) 0.0184(6) Uani 1 1 d . . . H13 H -0.2471 0.0123 -0.6530 0.022 Uiso 1 1 calc R . . C14 C -0.2568(3) 0.0424(2) -0.5022(2) 0.0216(6) Uani 1 1 d . . . H14 H -0.3140 -0.0471 -0.5148 0.026 Uiso 1 1 calc R . . C15 C -0.2210(4) 0.1332(2) -0.39108(19) 0.0271(6) Uani 1 1 d . . . H15A H -0.1576 0.0921 -0.3477 0.033 Uiso 1 1 calc R . . H15B H -0.3456 0.1462 -0.3639 0.033 Uiso 1 1 calc R . . C16 C -0.0953(4) 0.2679(2) -0.37849(19) 0.0269(6) Uani 1 1 d . . . H16A H -0.1216 0.3337 -0.3131 0.032 Uiso 1 1 calc R . . H16B H 0.0412 0.2628 -0.3702 0.032 Uiso 1 1 calc R . . C17 C -0.1276(3) 0.3154(2) -0.47122(18) 0.0188(6) Uani 1 1 d . . . H17 H -0.0226 0.3936 -0.4618 0.023 Uiso 1 1 calc R . . C18 C 0.0902(3) 0.2170(2) -0.6050(2) 0.0243(6) Uani 1 1 d . . . H18A H 0.1612 0.1960 -0.5512 0.036 Uiso 1 1 calc R . . H18B H 0.1495 0.3048 -0.6049 0.036 Uiso 1 1 calc R . . H18C H 0.0933 0.1519 -0.6746 0.036 Uiso 1 1 calc R . . H52 H -0.702(5) 0.517(3) -0.284(2) 0.054(11) Uiso 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 S1 0.0299(4) 0.0200(4) 0.0198(4) 0.0075(3) 0.0123(3) 0.0099(3) O1 0.0468(12) 0.0342(11) 0.0279(11) 0.0195(9) 0.0238(9) 0.0180(9) C1 0.0192(13) 0.0192(13) 0.0303(15) 0.0116(12) 0.0070(11) 0.0071(10) S2 0.0246(4) 0.0204(4) 0.0218(4) 0.0074(3) 0.0095(3) 0.0097(3) O2 0.0312(10) 0.0187(9) 0.0226(10) 0.0121(8) 0.0125(8) 0.0100(8) C2 0.0214(13) 0.0175(13) 0.0190(14) 0.0087(11) 0.0037(11) 0.0049(10) O3 0.0313(10) 0.0311(10) 0.0236(10) 0.0113(8) 0.0174(8) 0.0111(8) C3 0.0186(13) 0.0171(13) 0.0132(13) 0.0054(10) 0.0047(10) 0.0050(10) O4 0.0202(9) 0.0225(9) 0.0217(10) 0.0128(8) 0.0115(7) 0.0102(7) C4 0.0171(13) 0.0164(13) 0.0162(13) 0.0016(11) 0.0032(10) 0.0044(10) O5 0.0329(11) 0.0248(11) 0.0211(11) 0.0113(9) 0.0083(9) 0.0153(9) C5 0.0175(13) 0.0177(13) 0.0276(15) 0.0067(12) 0.0079(11) 0.0067(10) C6 0.0260(15) 0.0259(14) 0.0308(16) 0.0160(13) 0.0076(12) 0.0121(12) C7 0.0230(14) 0.0251(14) 0.0221(15) 0.0094(12) -0.0002(11) 0.0091(11) C8 0.0169(13) 0.0190(13) 0.0170(14) 0.0055(11) 0.0038(11) 0.0024(10) C9 0.0225(14) 0.0229(14) 0.0253(15) 0.0093(12) 0.0088(11) 0.0077(11) C10 0.0152(13) 0.0289(14) 0.0188(14) 0.0109(11) 0.0032(11) 0.0081(11) C11 0.0145(12) 0.0193(13) 0.0193(14) 0.0092(11) 0.0051(11) 0.0051(10) C12 0.0124(12) 0.0187(13) 0.0170(13) 0.0076(11) 0.0015(10) 0.0054(10) C13 0.0178(13) 0.0182(13) 0.0180(14) 0.0036(11) 0.0015(11) 0.0056(10) C14 0.0176(13) 0.0190(13) 0.0302(16) 0.0098(12) 0.0016(11) 0.0060(10) C15 0.0338(16) 0.0291(15) 0.0244(16) 0.0171(13) 0.0009(12) 0.0066(12) C16 0.0322(15) 0.0295(15) 0.0176(14) 0.0086(12) -0.0052(12) 0.0036(12) C17 0.0160(13) 0.0206(13) 0.0200(14) 0.0094(11) 0.0000(11) -0.0001(10) C18 0.0170(13) 0.0312(15) 0.0318(16) 0.0176(13) 0.0056(12) 0.0093(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 O1 1.5180(17) . ? S1 C1 1.808(3) . ? S1 C8 1.856(2) . ? C1 C2 1.517(3) . ? S2 O3 1.5135(17) . ? S2 C10 1.812(2) . ? S2 C17 1.849(2) . ? O2 C2 1.420(3) . ? C2 C3 1.542(3) . ? C3 C4 1.515(3) . ? C3 C8 1.537(3) . ? C3 C9 1.538(3) . ? O4 C11 1.431(3) . ? C4 C5 1.321(3) . ? C5 C6 1.494(3) . ? C6 C7 1.527(3) . ? C7 C8 1.526(3) . ? C10 C11 1.513(3) . ? C11 C12 1.550(3) . ? C12 C13 1.507(3) . ? C12 C18 1.530(3) . ? C12 C17 1.540(3) . ? C13 C14 1.325(3) . ? C14 C15 1.485(3) . ? C15 C16 1.536(3) . ? C16 C17 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 O1 S1 C1 106.96(11) . . ? O1 S1 C8 109.32(10) . . ? C1 S1 C8 92.57(10) . . ? C2 C1 S1 104.86(16) . . ? O3 S2 C10 106.37(10) . . ? O3 S2 C17 109.95(10) . . ? C10 S2 C17 92.51(10) . . ? O2 C2 C1 106.35(18) . . ? O2 C2 C3 112.08(19) . . ? C1 C2 C3 105.81(18) . . ? C4 C3 C8 111.17(19) . . ? C4 C3 C9 109.48(18) . . ? C8 C3 C9 111.00(19) . . ? C4 C3 C2 108.36(19) . . ? C8 C3 C2 105.45(18) . . ? C9 C3 C2 111.30(19) . . ? C5 C4 C3 125.5(2) . . ? C4 C5 C6 124.0(2) . . ? C5 C6 C7 112.5(2) . . ? C8 C7 C6 114.3(2) . . ? C7 C8 C3 114.62(19) . . ? C7 C8 S1 112.92(16) . . ? C3 C8 S1 108.11(15) . . ? C11 C10 S2 107.25(16) . . ? O4 C11 C10 107.64(18) . . ? O4 C11 C12 111.63(18) . . ? C10 C11 C12 105.78(18) . . ? C13 C12 C18 110.20(19) . . ? C13 C12 C17 110.54(18) . . ? C18 C12 C17 110.70(19) . . ? C13 C12 C11 108.59(19) . . ? C18 C12 C11 111.38(18) . . ? C17 C12 C11 105.32(18) . . ? C14 C13 C12 125.3(2) . . ? C13 C14 C15 124.4(2) . . ? C14 C15 C16 113.1(2) . . ? C17 C16 C15 113.8(2) . . ? C16 C17 C12 114.37(19) . . ? C16 C17 S2 112.71(17) . . ? C12 C17 S2 108.34(15) . . ? loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA _geom_hbond_site_symmetry_A O2 H2 O5 0.84 1.82 2.656(2) 171.9 . O5 H51 O3 0.90(3) 1.81(3) 2.707(2) 177(3) . O4 H4 O1 0.84 1.85 2.682(2) 171.4 1_654 O5 H52 O4 0.81(3) 2.01(4) 2.814(3) 174(3) 2_464 _diffrn_measured_fraction_theta_max 0.590 _diffrn_reflns_theta_full 27.44 _diffrn_measured_fraction_theta_full 0.590 _refine_diff_density_max 0.436 _refine_diff_density_min -0.358 _refine_diff_density_rms 0.065