# Supplementary Material (ESI) for Organic & Biomolecular Chemistry # This journal is © The Royal Society of Chemistry 2003 data_global _publ_contact_author_email agarcia@ugr.es _publ_contact_author_name 'Prof Andres Garcia-Granados' _journal_name_full Org.Biomol.Chem. _journal_coden_Cambridge 0177 _journal_year ? _journal_volume ? _journal_page_first ? loop_ _publ_author_name A.Garcia-Granados M.C.Gutierrez F.Rivas #==END#=============================================================== #============================================================================== data_1-oxo-4b,6b-diyl-S(S)-cyclic_sulphite _database_code_CSD 203948 #============================================================================== # 5. CHEMICAL DATA _chemical_name_systematic ; 1-OXO-4B,6B-DIYL-S(S)-CYCLIC SULPHITE ; _chemical_name_common '1-OXO-4B,6B-DIYL-S(S)-CYCLIC SULPHITE' _chemical_formula_moiety ? _chemical_formula_structural ? _chemical_formula_analytical ? _chemical_formula_sum 'C15 H24 O4 S' _chemical_formula_weight 300.4 _chemical_melting_point ? _chemical_compound_source ? 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' #============================================================================== # 6. CRYSTAL DATA _symmetry_cell_setting orthorhombic _symmetry_space_group_name_H-M 'P 212121' _symmetry_space_group_name_Hall ? loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, -y, z+1/2' '-x, y+1/2, -z+1/2' 'x+1/2, -y+1/2, -z' _cell_length_a 8.519(1) _cell_length_b 9.782(1) _cell_length_c 18.631(2) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 1552.6(2) _cell_formula_units_Z 4 _cell_measurement_temperature 294(1) _cell_measurement_reflns_used 38 _cell_measurement_theta_min 10 _cell_measurement_theta_max 12.5 _cell_special_details ; ? ; _exptl_crystal_description 'short prism' _exptl_crystal_colour colourless _exptl_crystal_size_max 0.60 _exptl_crystal_size_mid 0.40 _exptl_crystal_size_min 0.25 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.285 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 648 _exptl_absorpt_coefficient_mu 0.219 _exptl_absorpt_correction_type empirical _exptl_absorpt_correction_T_min 0.825 _exptl_absorpt_correction_T_max 0.950 #============================================================================== # 7. EXPERIMENTAL DATA _exptl_special_details ; ? ; _diffrn_ambient_temperature 294 _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 3332 _diffrn_reflns_av_R_equivalents 0.0349 _diffrn_reflns_av_sigmaI/netI 0.0396 _diffrn_reflns_limit_h_min -1 _diffrn_reflns_limit_h_max 11 _diffrn_reflns_limit_k_min -1 _diffrn_reflns_limit_k_max 13 _diffrn_reflns_limit_l_min -1 _diffrn_reflns_limit_l_max 26 _diffrn_reflns_theta_min 2.19 _diffrn_reflns_theta_max 30.00 _reflns_number_total 3129 _reflns_number_gt 2609 _reflns_threshold_expression >2sigma(I) _computing_data_collection ? _computing_cell_refinement ? _computing_data_reduction ? _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics ? _computing_publication_material ? #============================================================================== # 8. REFINEMENT DATA _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^)+(0.0613P)^2^+0.0749P] 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 -0.20(9) _refine_ls_number_reflns 3129 _refine_ls_number_parameters 193 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0535 _refine_ls_R_factor_gt 0.0409 _refine_ls_wR_factor_ref 0.1086 _refine_ls_wR_factor_gt 0.1006 _refine_ls_goodness_of_fit_ref 1.028 _refine_ls_restrained_S_all 1.028 _refine_ls_shift/su_max 0.002 _refine_ls_shift/su_mean 0.000 #============================================================================== # 9. ATOMIC COORDINATES AND THERMAL PARAMETERS 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 S S 0.87577(7) 0.64014(5) 0.13216(3) 0.04213(14) Uani 1 1 d . . . O1 O 0.9532(3) 1.2356(2) 0.01675(12) 0.0779(7) Uani 1 1 d . . . O2 O 0.76360(17) 0.76465(14) 0.15503(7) 0.0357(3) Uani 1 1 d . . . O3 O 1.0018(2) 0.72167(16) 0.08455(8) 0.0477(4) Uani 1 1 d . . . O4 O 0.9516(2) 0.59094(17) 0.19693(10) 0.0574(5) Uani 1 1 d . . . C1 C 0.9822(3) 1.1230(2) 0.03975(11) 0.0464(5) Uani 1 1 d . . . C2 C 1.1432(3) 1.0611(3) 0.03146(14) 0.0557(7) Uani 1 1 d . . . H2A H 1.2091 1.0964 0.0675 0.067 Uiso 1 1 calc R . . H2B H 1.1849 1.0878 -0.0131 0.067 Uiso 1 1 calc R . . C3 C 1.1450(3) 0.9067(3) 0.03585(13) 0.0530(6) Uani 1 1 d . . . H3A H 1.251 0.8751 0.03194 0.064 Uiso 1 1 calc R . . H3B H 1.0871 0.8700 -0.0036 0.064 Uiso 1 1 calc R . . C4 C 1.0742(2) 0.8540(2) 0.10623(11) 0.0401(4) Uani 1 1 d . . . C5 C 0.9494(2) 0.95243(19) 0.13639(10) 0.0315(4) Uani 1 1 d . . . H5A H 1.0099 1.0211 0.1651 0.038 Uiso 1 1 calc R . . C6 C 0.8433(2) 0.88028(19) 0.19083(9) 0.0308(4) Uani 1 1 d . . . H6A H 0.9078 0.8445 0.2284 0.037 Uiso 1 1 calc R . . C7 C 0.7181(2) 0.9710(2) 0.22448(11) 0.0367(4) Uani 1 1 d . . . H7A H 0.7719 1.0357 0.2531 0.044 Uiso 1 1 calc R . . C8 C 0.6311(3) 1.0523(3) 0.16704(14) 0.0518(6) Uani 1 1 d . . . H8A H 0.5655 0.9862 0.1361 0.062 Uiso 1 1 calc R . . H8B H 0.5549 1.1196 0.1915 0.062 Uiso 1 1 calc R . . C9 C 0.7429(3) 1.1316(3) 0.11886(12) 0.0516(6) Uani 1 1 d . . . H9A H 0.7966 1.1919 0.1455 0.062 Uiso 1 1 calc R . . H9B H 0.6871 1.1787 0.0864 0.062 Uiso 1 1 calc R . . C10 C 0.8598(3) 1.0373(2) 0.07941(10) 0.0382(4) Uani 1 1 d . . . C11 C 0.6105(3) 0.8908(2) 0.27542(11) 0.0415(5) Uani 1 1 d . . . H11A H 0.5485 0.8234 0.2455 0.050 Uiso 1 1 calc R . . C12 C 0.7029(3) 0.8096(3) 0.33075(12) 0.0580(7) Uani 1 1 d . . . H12A H 0.7776 0.7503 0.3064 0.087 Uiso 1 1 calc R . . H12B H 0.6310 0.7542 0.3591 0.087 Uiso 1 1 calc R . . H12C H 0.7592 0.8722 0.3622 0.087 Uiso 1 1 calc R . . C13 C 0.4926(4) 0.9843(3) 0.31393(17) 0.0664(8) Uani 1 1 d . . . H13A H 0.4281 0.9315 0.3440 0.100 Uiso 1 1 calc R . . H13B H 0.4303 1.0295 0.2798 0.100 Uiso 1 1 calc R . . H13C H 0.5472 1.0491 0.3415 0.100 Uiso 1 1 calc R . . C14 C 0.7691(3) 0.9555(3) 0.02188(12) 0.0537(6) Uani 1 1 d . . . H14A H 0.6925 0.9014 0.0442 0.081 Uiso 1 1 calc R . . H14B H 0.8391 0.8992 -0.0033 0.081 Uiso 1 1 calc R . . H14C H 0.7207 1.0161 -0.0101 0.081 Uiso 1 1 calc R . . C15 C 1.2022(3) 0.8261(3) 0.16085(15) 0.0557(6) Uani 1 1 d . . . H15A H 1.2736 0.7675 0.1418 0.084 Uiso 1 1 calc R . . H15B H 1.1593 0.7884 0.2008 0.084 Uiso 1 1 calc R . . H15C H 1.2504 0.9058 0.1726 0.084 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 S 0.0508(3) 0.0312(2) 0.0443(2) 0.0004(2) 0.0005(3) -0.0002(2) O1 0.0818(14) 0.0551(11) 0.0967(14) 0.0394(11) 0.0111(13) 0.0021(12) O2 0.0360(7) 0.0322(6) 0.0390(6) -0.0003(6) -0.0040(6) -0.0022(6) O3 0.0592(9) 0.0365(7) 0.0473(7) -0.0042(7) 0.0137(8) 0.0000(8) O4 0.0622(10) 0.0491(9) 0.0610(10) 0.0177(8) -0.0032(9) 0.0113(9) C1 0.0586(13) 0.0422(12) 0.0385(9) 0.0102(9) -0.0017(10) -0.0072(11) C2 0.0646(16) 0.0476(13) 0.0551(13) 0.0071(11) 0.0201(13) -0.0107(13) C3 0.0598(15) 0.0500(12) 0.0492(12) 0.0000(10) 0.0208(12) -0.0011(12) C4 0.0420(10) 0.0376(9) 0.0406(9) 0.0029(9) 0.0074(8) -0.0002(10) C5 0.0344(8) 0.0320(8) 0.0283(7) 0.0000(7) -0.0007(8) -0.0021(8) C6 0.0319(8) 0.0321(9) 0.0286(7) 0.0018(7) -0.0012(7) -0.0017(8) C7 0.0379(9) 0.0332(9) 0.0391(9) -0.0022(8) 0.0038(8) 0.0002(9) C8 0.0438(11) 0.0493(12) 0.0622(13) 0.0124(11) 0.0057(12) 0.0144(12) C9 0.0562(13) 0.0410(10) 0.0577(12) 0.0150(11) 0.0018(11) 0.0116(12) C10 0.0454(11) 0.0357(9) 0.0334(8) 0.0064(8) -0.0017(9) -0.0032(10) C11 0.0379(9) 0.0450(11) 0.0415(9) -0.0023(9) 0.0079(9) -0.0046(10) C12 0.0588(14) 0.0740(17) 0.0413(11) 0.0154(12) 0.0094(11) -0.0051(15) C13 0.0610(15) 0.0650(17) 0.0733(17) -0.0059(15) 0.0314(15) 0.0010(15) C14 0.0626(14) 0.0593(14) 0.0391(10) 0.0077(10) -0.0166(11) -0.0106(14) C15 0.0368(11) 0.0631(16) 0.0672(14) 0.0078(13) 0.0003(11) 0.0071(12) #============================================================================== # 10. MOLECULAR GEOMETRY _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 S O2 1.6056(15) . ? S O3 1.6051(17) . ? S O4 1.4508(18) . ? O2 C6 1.478(2) . ? O3 C4 1.489(3) . ? C1 O1 1.207(3) . ? C1 C2 1.507(4) . ? C2 C3 1.512(4) . ? C4 C3 1.533(3) . ? C4 C15 1.516(3) . ? C5 C4 1.540(3) . ? C5 C6 1.531(3) . ? C5 C10 1.549(3) . ? C6 C7 1.522(3) . ? C7 C8 1.525(3) . ? C7 C11 1.535(3) . ? C8 C9 1.522(3) . ? C10 C1 1.529(3) . ? C10 C9 1.544(3) . ? C10 C14 1.545(3) . ? C11 C12 1.521(3) . ? C11 C13 1.537(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 C1 C2 121.1(2) . . ? O1 C1 C10 122.1(2) . . ? O2 C6 C5 108.97(14) . . ? O2 C6 C7 108.07(14) . . ? O3 S O2 99.67(8) . . ? O3 C4 C3 102.90(17) . . ? O3 C4 C5 110.91(16) . . ? O3 C4 C15 108.89(18) . . ? O4 S O2 107.21(9) . . ? O4 S O3 109.08(10) . . ? C1 C2 C3 113.9(2) . . ? C1 C10 C5 106.79(18) . . ? C1 C10 C9 110.04(19) . . ? C1 C10 C14 106.86(17) . . ? C2 C1 C10 116.74(19) . . ? C2 C3 C4 112.2(2) . . ? C3 C4 C5 111.93(18) . . ? C4 O3 S 123.97(13) . . ? C4 C5 C10 115.17(16) . . ? C6 O2 S 115.27(11) . . ? C6 C5 C4 111.16(16) . . ? C6 C5 C10 114.19(16) . . ? C6 C7 C8 110.81(17) . . ? C6 C7 C11 112.03(17) . . ? C7 C6 C5 114.71(16) . . ? C7 C11 C13 112.01(19) . . ? C8 C7 C11 114.23(18) . . ? C8 C9 C10 112.3(2) . . ? C9 C8 C7 112.06(19) . . ? C9 C10 C5 108.18(16) . . ? C9 C10 C14 108.5(2) . . ? C12 C11 C7 112.18(18) . . ? C12 C11 C13 109.4(2) . . ? C14 C10 C5 116.35(18) . . ? C15 C4 C3 110.55(19) . . ? C15 C4 C5 111.33(18) . . ? _diffrn_measured_fraction_theta_max 1.000 _diffrn_reflns_theta_full 30.00 _diffrn_measured_fraction_theta_full 1.000 _refine_diff_density_max 0.197 _refine_diff_density_min -0.236 _refine_diff_density_rms 0.052 #==END data_1-oxo-4b,6b-diyl-S(R)-cyclic_sulphite _database_code_CSD 203949 #============================================================================== # 5. CHEMICAL DATA _chemical_name_systematic ; 1-OXO-4B,6B-DIYL-S(R)-CYCLIC SULPHITE ; _chemical_name_common '1-OXO-4B,6B-DIYL-S(R)-CYCLIC SULPHITE' _chemical_formula_moiety ? _chemical_formula_structural ? _chemical_formula_analytical ? _chemical_formula_sum 'C15 H24 O4 S' _chemical_formula_weight 300.4 _chemical_melting_point ? _chemical_compound_source ? 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' #============================================================================== # 6. CRYSTAL DATA _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M 'P 21' _symmetry_space_group_name_Hall ? loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z' _cell_length_a 9.321(2) _cell_length_b 7.996(2) _cell_length_c 11.132(2) _cell_angle_alpha 90.00 _cell_angle_beta 106.32(3) _cell_angle_gamma 90.00 _cell_volume 796.2(3) _cell_formula_units_Z 2 _cell_measurement_temperature 294(1) _cell_measurement_reflns_used 29 _cell_measurement_theta_min 15 _cell_measurement_theta_max 18.2 _cell_special_details ; ? ; _exptl_crystal_description 'short prism' _exptl_crystal_colour colourless _exptl_crystal_size_max 0.45 _exptl_crystal_size_mid 0.30 _exptl_crystal_size_min 0.25 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.253 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 324 _exptl_absorpt_coefficient_mu 0.213 _exptl_absorpt_correction_type empirical _exptl_absorpt_correction_T_min 0.834 _exptl_absorpt_correction_T_max 0.967 #============================================================================== # 7. EXPERIMENTAL DATA _exptl_special_details ; ? ; _diffrn_ambient_temperature 294(1) _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 3060 _diffrn_reflns_av_R_equivalents 0.0000 _diffrn_reflns_av_sigmaI/netI 0.0330 _diffrn_reflns_limit_h_min -14 _diffrn_reflns_limit_h_max 13 _diffrn_reflns_limit_k_min 0 _diffrn_reflns_limit_k_max 12 _diffrn_reflns_limit_l_min 0 _diffrn_reflns_limit_l_max 16 _diffrn_reflns_theta_min 1.91 _diffrn_reflns_theta_max 32.53 _reflns_number_total 3060 _reflns_number_gt 2084 _reflns_threshold_expression >2sigma(I) _computing_data_collection ? _computing_cell_refinement ? _computing_data_reduction ? _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics ? _computing_publication_material ? #============================================================================== # 8. REFINEMENT DATA _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^)+(0.0626P)^2^+0.1946P] 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 -0.18(16) _refine_ls_number_reflns 3060 _refine_ls_number_parameters 193 _refine_ls_number_restraints 1 _refine_ls_R_factor_all 0.1050 _refine_ls_R_factor_gt 0.0672 _refine_ls_wR_factor_ref 0.1730 _refine_ls_wR_factor_gt 0.1455 _refine_ls_goodness_of_fit_ref 1.167 _refine_ls_restrained_S_all 1.166 _refine_ls_shift/su_max 0.053 _refine_ls_shift/su_mean 0.009 #============================================================================== # 9. ATOMIC COORDINATES AND THERMAL PARAMETERS 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 S S 0.96562(11) 0.21542(15) 0.25403(9) 0.0594(3) Uani 1 1 d . . . O1 O 0.8122(3) 0.1710(5) 0.2021(3) 0.0804(12) Uani 1 1 d . . . O2 O 1.0550(3) 0.1141(4) 0.1718(2) 0.0546(7) Uani 1 1 d . . . O3 O 1.0178(3) 0.1045(4) 0.3810(2) 0.0540(7) Uani 1 1 d . . . O4 O 1.3894(4) -0.3834(5) 0.4623(4) 0.0791(10) Uani 1 1 d . . . C1 C 1.3290(4) -0.2476(6) 0.4559(4) 0.0577(10) Uani 1 1 d . . . C2 C 1.3269(5) -0.1502(7) 0.5705(4) 0.0677(13) Uani 1 1 d . . . H2A H 1.414 -0.083 0.5953 0.081 Uiso 1 1 calc R . . H2B H 1.3290 -0.226 0.637 0.081 Uiso 1 1 calc R . . C3 C 1.1885(5) -0.0383(7) 0.5487(4) 0.0609(11) Uani 1 1 d . . . H3A H 1.1912 0.020 0.625 0.073 Uiso 1 1 calc R . . H3B H 1.100 -0.107 0.5266 0.073 Uiso 1 1 calc R . . C4 C 1.1809(4) 0.0895(5) 0.4440(3) 0.0476(8) Uani 1 1 d . . . C5 C 1.2601(4) 0.0246(5) 0.3493(3) 0.0417(7) Uani 1 1 d . . . H5A H 1.359 0.0473 0.3850 0.050 Uiso 1 1 calc R . . C6 C 1.2177(4) 0.1257(5) 0.2282(3) 0.0448(7) Uani 1 1 d . . . H6A H 1.2420 0.238 0.2483 0.054 Uiso 1 1 calc R . . C7 C 1.2952(5) 0.0713(6) 0.1314(4) 0.0539(10) Uani 1 1 d . . . H7A H 1.399 0.0937 0.1666 0.065 Uiso 1 1 calc R . . C8 C 1.2808(6) -0.1183(6) 0.1118(4) 0.0654(12) Uani 1 1 d . . . H8A H 1.176 -0.1471 0.0742 0.078 Uiso 1 1 calc R . . H8B H 1.337 -0.1528 0.054 0.078 Uiso 1 1 calc R . . C9 C 1.3391(5) -0.2121(6) 0.2345(4) 0.0623(11) Uani 1 1 d . . . H9A H 1.447 -0.1849 0.2716 0.075 Uiso 1 1 calc R . . H9B H 1.3307 -0.335 0.2178 0.075 Uiso 1 1 calc R . . C10 C 1.2527(4) -0.1673(5) 0.3286(4) 0.0487(8) Uani 1 1 d . . . C11 C 1.2450(6) 0.1744(7) 0.0093(4) 0.0712(15) Uani 1 1 d . . . H11A H 1.149 0.1494 -0.028 0.085 Uiso 1 1 calc R . . C12 C 1.3359(7) 0.1280(11) -0.0806(5) 0.106(2) Uani 1 1 d . . . H12A H 1.3299 0.010 -0.0951 0.158 Uiso 1 1 calc R . . H12B H 1.438 0.1593 -0.0448 0.158 Uiso 1 1 calc R . . H12C H 1.2969 0.185 -0.158 0.158 Uiso 1 1 calc R . . C13 C 1.2549(9) 0.3617(9) 0.0347(6) 0.100(2) Uani 1 1 d . . . H13A H 1.195 0.3904 0.092 0.149 Uiso 1 1 calc R . . H13B H 1.2164 0.423 -0.045 0.149 Uiso 1 1 calc R . . H13C H 1.360 0.3931 0.0733 0.149 Uiso 1 1 calc R . . C14 C 1.0943(5) -0.2443(6) 0.2862(5) 0.0681(12) Uani 1 1 d . . . H14A H 1.0413 -0.1987 0.207 0.102 Uiso 1 1 calc R . . H14B H 1.0423 -0.2193 0.346 0.102 Uiso 1 1 calc R . . H14C H 1.1019 -0.362 0.2789 0.102 Uiso 1 1 calc R . . C15 C 1.2413(5) 0.2577(6) 0.4989(4) 0.0614(11) Uani 1 1 d . . . H15A H 1.1890 0.2931 0.5566 0.092 Uiso 1 1 calc R . . H15B H 1.2277 0.338 0.4335 0.092 Uiso 1 1 calc R . . H15C H 1.345 0.2475 0.5411 0.092 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 S 0.0601(6) 0.0624(6) 0.0523(5) -0.0060(5) 0.0105(4) 0.0192(5) O1 0.0546(15) 0.117(4) 0.0625(17) -0.0168(19) 0.0047(13) 0.0228(19) O2 0.0525(14) 0.0649(18) 0.0422(12) -0.0034(13) 0.0064(11) 0.0157(14) O3 0.0475(13) 0.0644(17) 0.0491(13) -0.0052(14) 0.0116(11) 0.0047(14) O4 0.070(2) 0.060(2) 0.103(3) 0.027(2) 0.0181(19) 0.0123(17) C1 0.0460(19) 0.053(3) 0.072(2) 0.021(2) 0.0137(18) -0.0032(18) C2 0.066(3) 0.080(3) 0.053(2) 0.025(2) 0.0104(19) -0.005(2) C3 0.059(2) 0.077(3) 0.047(2) 0.008(2) 0.0157(17) -0.003(2) C4 0.0468(17) 0.053(2) 0.0415(16) -0.0011(16) 0.0102(14) -0.0013(17) C5 0.0410(16) 0.0432(18) 0.0382(16) 0.0008(14) 0.0067(13) -0.0019(14) C6 0.0522(18) 0.0397(19) 0.0404(16) -0.0004(14) 0.0096(14) 0.0027(15) C7 0.054(2) 0.066(3) 0.0418(18) 0.0018(18) 0.0130(16) 0.0034(19) C8 0.076(3) 0.072(3) 0.047(2) -0.009(2) 0.016(2) 0.015(2) C9 0.068(3) 0.053(2) 0.065(3) -0.006(2) 0.017(2) 0.013(2) C10 0.0442(18) 0.0425(18) 0.056(2) -0.0019(16) 0.0081(16) 0.0002(15) C11 0.074(3) 0.098(4) 0.0418(19) 0.013(2) 0.0155(19) 0.002(3) C12 0.131(5) 0.141(6) 0.059(3) 0.009(4) 0.050(3) 0.005(5) C13 0.147(6) 0.083(4) 0.069(3) 0.028(3) 0.032(4) 0.005(4) C14 0.059(2) 0.053(3) 0.084(3) -0.005(2) 0.007(2) -0.008(2) C15 0.065(2) 0.066(3) 0.052(2) -0.016(2) 0.0141(18) -0.008(2) #============================================================================== # 10. MOLECULAR GEOMETRY _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 S O1 1.428(3) . ? S O2 1.617(3) . ? S O3 1.623(3) . ? O3 C4 1.489(4) . ? O4 C1 1.216(6) . ? C1 C2 1.499(7) . ? C3 C2 1.532(7) . ? C4 C3 1.537(6) . ? C4 C5 1.537(5) . ? C4 C15 1.519(6) . ? C5 C10 1.550(5) . ? C6 O2 1.472(4) . ? C6 C5 1.526(5) . ? C6 C7 1.520(5) . ? C7 C8 1.532(7) . ? C7 C11 1.545(6) . ? C9 C8 1.519(6) . ? C10 C1 1.536(5) . ? C10 C9 1.532(6) . ? C10 C14 1.546(5) . ? C11 C12 1.528(7) . ? C11 C13 1.522(9) . ? 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 S O2 105.21(18) . . ? O1 S O3 103.7(2) . . ? O2 S O3 98.23(15) . . ? O2 C6 C5 108.9(3) . . ? O2 C6 C7 108.5(3) . . ? O3 C4 C3 103.6(3) . . ? O3 C4 C5 109.2(3) . . ? O3 C4 C15 109.4(3) . . ? O4 C1 C2 122.1(4) . . ? O4 C1 C10 120.9(5) . . ? C1 C2 C3 112.3(4) . . ? C1 C10 C5 106.7(3) . . ? C1 C10 C14 105.6(3) . . ? C2 C1 C10 117.0(4) . . ? C2 C3 C4 111.5(3) . . ? C3 C4 C5 111.5(3) . . ? C4 O3 S 118.1(2) . . ? C4 C5 C10 115.2(3) . . ? C6 O2 S 111.1(2) . . ? C6 C5 C4 111.8(3) . . ? C6 C5 C10 113.8(3) . . ? C6 C7 C8 110.1(4) . . ? C6 C7 C11 112.6(4) . . ? C7 C6 C5 114.7(3) . . ? C8 C7 C11 114.2(4) . . ? C8 C9 C10 112.1(4) . . ? C9 C8 C7 111.4(4) . . ? C9 C10 C1 109.7(3) . . ? C9 C10 C5 108.9(3) . . ? C9 C10 C14 109.8(4) . . ? C12 C11 C7 111.1(5) . . ? C13 C11 C7 112.0(4) . . ? C13 C11 C12 110.1(6) . . ? C14 C10 C5 116.0(3) . . ? C15 C4 C3 110.5(3) . . ? C15 C4 C5 112.3(3) . . ? _diffrn_measured_fraction_theta_max 0.998 _diffrn_reflns_theta_full 32.53 _diffrn_measured_fraction_theta_full 0.998 _refine_diff_density_max 0.304 _refine_diff_density_min -0.298 _refine_diff_density_rms 0.053