data_global _publ_contact_author_email ALBERTO.AVENOZA@DQ.UNIRIOJA.ES _publ_contact_author_name 'Prof Alberto Avenoza' _journal_name_full Chem.Commun. _journal_coden_Cambridge 0182 _publ_contact_author_address ; Chemistry University of La Rioja Madre de Dios, 51 Logrono La Rioja E-26006 SPAIN ; _publ_section_title ; SN2 vs E2 on quaternary centres: an application to the synthesis of enantiopure beta-2,2-amino acids ; loop_ _publ_author_name 'Alberto Avenoza' 'Jesus H. Busto' 'Francisco Corzana' 'Gonzalo Jimenez-Oes' 'Jesus M. Peregrina' data_shelxl _database_code_depnum_ccdc_archive 'CCDC 227600' _chemical_name_common oso2 _audit_creation_method SHELXL-97 _chemical_name_systematic ; oso2 ; _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C7 H11 N1 O7 S1' _chemical_formula_weight 253.23 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' N N 0.0061 0.0033 '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 Orthorhombic _symmetry_space_group_name_H-M 'P 21 21 21 ' 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 8.2367(3) _cell_length_b 8.9543(4) _cell_length_c 14.8873(7) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 1098.00(8) _cell_formula_units_Z 4 _cell_measurement_temperature 173(2) _cell_measurement_reflns_used 13929 _cell_measurement_theta_min 1.018 _cell_measurement_theta_max 27.88 _exptl_crystal_description Prism _exptl_crystal_colour Colourless _exptl_crystal_size_max 0.5 _exptl_crystal_size_mid 0.27 _exptl_crystal_size_min 0.25 _exptl_crystal_density_meas 'not measured' _exptl_crystal_density_diffrn 1.532 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 528 _exptl_absorpt_coefficient_mu 0.316 _exptl_absorpt_correction_type none _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 173(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'normal-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type KappaCCD _diffrn_measurement_method CCD _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 13531 _diffrn_reflns_av_R_equivalents 0.1060 _diffrn_reflns_av_sigmaI/netI 0.0973 _diffrn_reflns_limit_h_min -13 _diffrn_reflns_limit_h_max 13 _diffrn_reflns_limit_k_min -13 _diffrn_reflns_limit_k_max 14 _diffrn_reflns_limit_l_min -24 _diffrn_reflns_limit_l_max 20 _diffrn_reflns_theta_min 3.36 _diffrn_reflns_theta_max 35.00 _reflns_number_total 4609 _reflns_number_gt 2849 _reflns_threshold_expression >2sigma(I) _computing_data_collection KappaCCD _computing_cell_refinement 'HKL Scalepack (Otwinowski & Minor 1997)' _computing_data_reduction 'Denzo and Scalepak (Otwinowski & Minor, 1997' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics ORTEP-III _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^ > 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^)+(0.0611P)^2^+0.2449P] 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(11) _refine_ls_number_reflns 4609 _refine_ls_number_parameters 145 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.1139 _refine_ls_R_factor_gt 0.0591 _refine_ls_wR_factor_ref 0.1591 _refine_ls_wR_factor_gt 0.1301 _refine_ls_goodness_of_fit_ref 1.016 _refine_ls_restrained_S_all 1.016 _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 0.92869(7) 0.10066(7) 0.49442(5) 0.03210(15) Uani 1 1 d . . . N2 N 0.9348(3) 0.2659(2) 0.54354(14) 0.0319(4) Uani 1 1 d . . . O3 O 1.1496(2) 0.1641(2) 0.74373(14) 0.0433(5) Uani 1 1 d . . . O4 O 0.8741(2) 0.01610(18) 0.58253(14) 0.0335(4) Uani 1 1 d . . . O5 O 0.9505(2) 0.5129(2) 0.54440(15) 0.0388(5) Uani 1 1 d . . . C6 C 0.8876(3) 0.2622(3) 0.63779(17) 0.0327(5) Uani 1 1 d . . . H6A H 0.9563 0.3285 0.6713 0.039 Uiso 1 1 d R . . H6B H 0.7767 0.2938 0.6435 0.039 Uiso 1 1 d R . . C7 C 0.9132(3) 0.0998(3) 0.66403(18) 0.0316(5) Uani 1 1 d . . . O8 O 0.9990(2) 0.3880(2) 0.41457(14) 0.0441(5) Uani 1 1 d . . . C9 C 0.9639(3) 0.3925(3) 0.4928(2) 0.0333(5) Uani 1 1 d . . . O10 O 1.1518(3) -0.0567(2) 0.67129(17) 0.0489(6) Uani 1 1 d . . . C11 C 1.0872(3) 0.0587(3) 0.69132(19) 0.0350(5) Uani 1 1 d . . . O12 O 1.0870(3) 0.0571(2) 0.46860(16) 0.0487(6) Uani 1 1 d . . . C13 C 0.7978(3) 0.0500(4) 0.7380(2) 0.0414(6) Uani 1 1 d . . . H13A H 0.8222 0.1042 0.7919 0.050 Uiso 1 1 d R . . H13B H 0.8110 -0.0550 0.7486 0.050 Uiso 1 1 d R . . H13C H 0.6877 0.0698 0.7203 0.050 Uiso 1 1 d R . . O14 O 0.8014(3) 0.0878(3) 0.43095(15) 0.0524(6) Uani 1 1 d . . . C15 C 1.3108(4) 0.1355(4) 0.7796(2) 0.0523(8) Uani 1 1 d . . . H15A H 1.3437 0.2180 0.8166 0.063 Uiso 1 1 d R . . H15B H 1.3867 0.1233 0.7313 0.063 Uiso 1 1 d R . . H15C H 1.3080 0.0461 0.8151 0.063 Uiso 1 1 d R . . C16 C 0.9812(4) 0.6530(3) 0.4988(3) 0.0602(9) Uani 1 1 d . . . H16A H 0.9699 0.7352 0.5398 0.072 Uiso 1 1 d R . . H16B H 0.9042 0.6635 0.4508 0.072 Uiso 1 1 d R . . H16C H 1.0892 0.6524 0.4745 0.072 Uiso 1 1 d 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(3) 0.0326(2) 0.0314(3) -0.0068(3) 0.0023(3) -0.0038(2) N2 0.0397(10) 0.0271(9) 0.0289(10) -0.0010(8) 0.0029(10) -0.0005(8) O3 0.0384(10) 0.0472(11) 0.0444(12) 0.0041(10) -0.0126(9) -0.0026(8) O4 0.0344(8) 0.0274(7) 0.0387(10) -0.0009(8) -0.0005(8) -0.0047(6) O5 0.0390(10) 0.0275(8) 0.0499(13) 0.0036(8) 0.0037(9) 0.0021(7) C6 0.0398(13) 0.0302(11) 0.0281(12) -0.0013(10) -0.0002(10) 0.0049(9) C7 0.0319(11) 0.0307(10) 0.0322(12) -0.0005(10) 0.0011(10) 0.0011(10) O8 0.0454(10) 0.0489(11) 0.0382(11) 0.0113(11) 0.0053(9) 0.0017(9) C9 0.0293(10) 0.0326(10) 0.0380(14) 0.0069(13) 0.0013(10) 0.0007(8) O10 0.0430(11) 0.0446(11) 0.0592(15) 0.0035(10) -0.0014(10) 0.0113(9) C11 0.0357(12) 0.0366(11) 0.0325(13) 0.0086(10) 0.0020(11) 0.0030(10) O12 0.0448(11) 0.0445(10) 0.0569(14) -0.0062(10) 0.0149(10) 0.0044(8) C13 0.0348(12) 0.0524(15) 0.0370(16) 0.0121(13) 0.0050(11) 0.0014(11) O14 0.0528(12) 0.0674(14) 0.0371(11) -0.0079(12) -0.0116(10) -0.0170(11) C15 0.0380(14) 0.067(2) 0.052(2) 0.0074(17) -0.0130(14) -0.0045(14) C16 0.0653(18) 0.0300(11) 0.085(3) 0.0188(18) 0.007(2) 0.0022(12) _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 O12 1.414(2) . ? S1 O14 1.416(2) . ? S1 O4 1.580(2) . ? S1 N2 1.651(2) . ? N2 C9 1.383(3) . ? N2 C6 1.456(3) . ? O3 C11 1.328(3) . ? O3 C15 1.454(3) . ? O4 C7 1.462(3) . ? O5 C9 1.329(3) . ? O5 C16 1.449(4) . ? C6 C7 1.521(4) . ? C6 H6A 0.9599 . ? C6 H6B 0.9600 . ? C7 C13 1.521(4) . ? C7 C11 1.534(4) . ? O8 C9 1.200(4) . ? O10 C11 1.199(3) . ? C13 H13A 0.9601 . ? C13 H13B 0.9600 . ? C13 H13C 0.9601 . ? C15 H15A 0.9599 . ? C15 H15B 0.9601 . ? C15 H15C 0.9599 . ? C16 H16A 0.9600 . ? C16 H16B 0.9600 . ? C16 H16C 0.9600 . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag O12 S1 O14 118.62(15) . . ? O12 S1 O4 110.84(12) . . ? O14 S1 O4 107.71(12) . . ? O12 S1 N2 109.85(12) . . ? O14 S1 N2 113.01(13) . . ? O4 S1 N2 94.04(10) . . ? C9 N2 C6 126.3(2) . . ? C9 N2 S1 119.83(19) . . ? C6 N2 S1 113.46(17) . . ? C11 O3 C15 116.4(3) . . ? C7 O4 S1 112.39(14) . . ? C9 O5 C16 114.6(3) . . ? N2 C6 C7 103.4(2) . . ? N2 C6 H6A 109.2 . . ? C7 C6 H6A 112.1 . . ? N2 C6 H6B 109.4 . . ? C7 C6 H6B 113.0 . . ? H6A C6 H6B 109.5 . . ? O4 C7 C6 104.3(2) . . ? O4 C7 C13 108.2(2) . . ? C6 C7 C13 112.3(2) . . ? O4 C7 C11 107.6(2) . . ? C6 C7 C11 115.3(2) . . ? C13 C7 C11 108.8(2) . . ? O8 C9 O5 127.5(2) . . ? O8 C9 N2 123.0(2) . . ? O5 C9 N2 109.5(2) . . ? O10 C11 O3 125.9(3) . . ? O10 C11 C7 123.7(3) . . ? O3 C11 C7 110.3(2) . . ? C7 C13 H13A 109.1 . . ? C7 C13 H13B 109.6 . . ? H13A C13 H13B 109.5 . . ? C7 C13 H13C 109.8 . . ? H13A C13 H13C 109.5 . . ? H13B C13 H13C 109.5 . . ? O3 C15 H15A 109.5 . . ? O3 C15 H15B 109.8 . . ? H15A C15 H15B 109.5 . . ? O3 C15 H15C 109.1 . . ? H15A C15 H15C 109.5 . . ? H15B C15 H15C 109.5 . . ? O5 C16 H16A 110.4 . . ? O5 C16 H16B 108.5 . . ? H16A C16 H16B 109.5 . . ? O5 C16 H16C 109.5 . . ? H16A C16 H16C 109.5 . . ? H16B C16 H16C 109.5 . . ? _diffrn_measured_fraction_theta_max 0.993 _diffrn_reflns_theta_full 35.00 _diffrn_measured_fraction_theta_full 0.993 _refine_diff_density_max 0.412 _refine_diff_density_min -0.509 _refine_diff_density_rms 0.076 data_shelxl_b _database_code_depnum_ccdc_archive 'CCDC 228173' _chemical_name_common OSO1 _audit_creation_method SHELXL-97 _chemical_name_systematic ; OSO1 ; _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C8 H14 N2 O7 S1' _chemical_formula_weight 282.27 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' N N 0.0061 0.0033 '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 Orthorhombic _symmetry_space_group_name_H-M 'P 21 21 21' 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 8.8646(3) _cell_length_b 10.9014(4) _cell_length_c 12.4336(5) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 1201.54(8) _cell_formula_units_Z 4 _cell_measurement_temperature 173(2) _cell_measurement_reflns_used 7208 _cell_measurement_theta_min 1.018 _cell_measurement_theta_max 27.87 _exptl_crystal_description Prism _exptl_crystal_colour Colourless _exptl_crystal_size_max 0.5 _exptl_crystal_size_mid 0.42 _exptl_crystal_size_min 0.32 _exptl_crystal_density_meas 'not measured' _exptl_crystal_density_diffrn 1.560 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 592 _exptl_absorpt_coefficient_mu 0.299 _exptl_absorpt_correction_type none _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 173(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'normal-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type KappaCCD _diffrn_measurement_method CCD _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 6535 _diffrn_reflns_av_R_equivalents 0.0545 _diffrn_reflns_av_sigmaI/netI 0.0517 _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 -9 _diffrn_reflns_limit_l_max 16 _diffrn_reflns_theta_min 3.74 _diffrn_reflns_theta_max 27.91 _reflns_number_total 2787 _reflns_number_gt 2530 _reflns_threshold_expression >2sigma(I) _computing_data_collection KappaCCD _computing_cell_refinement 'HKL Scalepack (Otwinowski & Minor 1997)' _computing_data_reduction 'Denzo and Scalepak (Otwinowski & Minor, 1997)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics ORTEP-III _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^ > 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^)+(0.0542P)^2^+0.2889P] 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(9) _refine_ls_number_reflns 2787 _refine_ls_number_parameters 163 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0460 _refine_ls_R_factor_gt 0.0400 _refine_ls_wR_factor_ref 0.1029 _refine_ls_wR_factor_gt 0.0998 _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 S1 S -0.25698(6) -0.48009(4) -0.33663(4) 0.02780(14) Uani 1 1 d . . . O2 O -0.21661(18) -0.81249(12) -0.05329(12) 0.0288(3) Uani 1 1 d . . . O3 O -0.05995(19) -0.38944(14) -0.07851(12) 0.0314(4) Uani 1 1 d . . . O4 O -0.3011(2) -0.85180(14) -0.32526(13) 0.0372(4) Uani 1 1 d . . . O5 O -0.1183(2) -0.27576(15) -0.22454(14) 0.0407(4) Uani 1 1 d . . . O6 O -0.1515(2) -0.46787(17) -0.42149(14) 0.0391(4) Uani 1 1 d . . . O7 O -0.30345(18) -0.61790(13) -0.32974(12) 0.0302(3) Uani 1 1 d . . . N8 N -0.2443(2) -0.87197(14) -0.15106(13) 0.0286(4) Uani 1 1 d . . . N9 N -0.1753(2) -0.47919(16) -0.21681(14) 0.0286(4) Uani 1 1 d . . . C10 C -0.3081(2) -0.66675(19) -0.21845(16) 0.0252(4) Uani 1 1 d . . . C11 C -0.4597(2) -0.6381(2) -0.1696(2) 0.0324(5) Uani 1 1 d . . . H11A H -0.4640 -0.6698 -0.0976 0.039 Uiso 1 1 d R . . H11B H -0.5377 -0.6752 -0.2121 0.039 Uiso 1 1 d R . . H11C H -0.4739 -0.5508 -0.1681 0.039 Uiso 1 1 d R . . C12 C -0.1166(3) -0.37080(18) -0.17593(17) 0.0285(4) Uani 1 1 d . . . C13 C 0.0039(3) -0.2818(2) -0.0267(2) 0.0358(5) Uani 1 1 d . . . H13A H 0.0418 -0.3038 0.0429 0.043 Uiso 1 1 d R . . H13B H -0.0731 -0.2204 -0.0191 0.043 Uiso 1 1 d R . . H13C H 0.0847 -0.2498 -0.0698 0.043 Uiso 1 1 d R . . C14 C -0.2834(2) -0.80542(18) -0.23662(16) 0.0261(4) Uani 1 1 d . . . C15 C -0.1756(2) -0.60011(17) -0.16432(17) 0.0248(4) Uani 1 1 d . . . H15A H -0.0808 -0.6401 -0.1771 0.030 Uiso 1 1 d R . . H15B H -0.1902 -0.5898 -0.0884 0.030 Uiso 1 1 d R . . C16 C -0.2083(3) -1.00163(19) -0.1564(2) 0.0362(5) Uani 1 1 d . . . H16A H -0.2319 -1.0319 -0.2269 0.043 Uiso 1 1 d R . . H16B H -0.2671 -1.0450 -0.1039 0.043 Uiso 1 1 d R . . H16C H -0.1029 -1.0140 -0.1421 0.043 Uiso 1 1 d R . . C17 C -0.3200(3) -0.8539(2) 0.02768(18) 0.0371(5) Uani 1 1 d . . . H17A H -0.2992 -0.8122 0.0941 0.044 Uiso 1 1 d R . . H17B H -0.3091 -0.9407 0.0379 0.044 Uiso 1 1 d R . . H17C H -0.4213 -0.8360 0.0053 0.044 Uiso 1 1 d R . . O18 O -0.3853(2) -0.40284(15) -0.33836(16) 0.0419(4) 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 S1 0.0347(3) 0.0233(2) 0.0253(2) 0.00497(18) -0.0026(2) 0.0009(2) O2 0.0379(9) 0.0240(7) 0.0245(7) 0.0007(5) -0.0033(6) -0.0051(6) O3 0.0429(9) 0.0234(7) 0.0280(7) 0.0012(6) -0.0031(7) -0.0055(7) O4 0.0584(10) 0.0261(7) 0.0271(8) -0.0043(6) -0.0022(8) -0.0020(7) O5 0.0612(11) 0.0248(7) 0.0360(9) 0.0059(7) -0.0054(8) -0.0058(8) O6 0.0455(10) 0.0434(9) 0.0286(8) 0.0090(7) 0.0030(7) -0.0070(8) O7 0.0426(8) 0.0242(7) 0.0237(7) 0.0030(6) -0.0054(7) -0.0022(6) N8 0.0392(9) 0.0197(7) 0.0270(8) -0.0008(6) -0.0034(9) 0.0010(7) N9 0.0401(9) 0.0205(8) 0.0250(8) 0.0027(7) -0.0054(7) -0.0034(8) C10 0.0333(10) 0.0216(9) 0.0208(9) 0.0022(7) -0.0001(8) 0.0023(8) C11 0.0316(10) 0.0286(10) 0.0369(12) 0.0032(10) 0.0030(10) 0.0015(8) C12 0.0355(10) 0.0227(9) 0.0272(10) 0.0015(8) 0.0009(9) -0.0028(8) C13 0.0472(13) 0.0268(10) 0.0335(11) -0.0035(9) -0.0008(11) -0.0083(10) C14 0.0307(11) 0.0228(9) 0.0248(9) 0.0002(7) 0.0000(8) -0.0023(8) C15 0.0312(9) 0.0192(9) 0.0240(9) 0.0023(8) -0.0011(9) -0.0010(7) C16 0.0456(12) 0.0207(10) 0.0423(12) 0.0010(9) -0.0037(11) 0.0023(8) C17 0.0476(13) 0.0387(12) 0.0249(10) 0.0049(9) 0.0025(10) -0.0052(11) O18 0.0435(9) 0.0310(8) 0.0513(11) 0.0059(8) -0.0073(9) 0.0078(7) _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 O18 1.4155(17) . ? S1 O6 1.4162(18) . ? S1 O7 1.5601(15) . ? S1 N9 1.6566(18) . ? O2 N8 1.400(2) . ? O2 C17 1.434(3) . ? O3 C12 1.327(3) . ? O3 C13 1.454(3) . ? O4 C14 1.223(3) . ? O5 C12 1.200(3) . ? O7 C10 1.483(2) . ? N8 C14 1.333(2) . ? N8 C16 1.451(2) . ? N9 C12 1.387(3) . ? N9 C15 1.471(2) . ? C10 C11 1.508(3) . ? C10 C15 1.536(3) . ? C10 C14 1.544(3) . ? C11 H11A 0.9600 . ? C11 H11B 0.9600 . ? C11 H11C 0.9600 . ? C13 H13A 0.9599 . ? C13 H13B 0.9601 . ? C13 H13C 0.9601 . ? C15 H15A 0.9600 . ? C15 H15B 0.9600 . ? C16 H16A 0.9600 . ? C16 H16B 0.9600 . ? C16 H16C 0.9599 . ? C17 H17A 0.9600 . ? C17 H17B 0.9599 . ? C17 H17C 0.9600 . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag O18 S1 O6 117.61(11) . . ? O18 S1 O7 111.19(10) . . ? O6 S1 O7 107.81(10) . . ? O18 S1 N9 111.19(11) . . ? O6 S1 N9 112.39(10) . . ? O7 S1 N9 94.11(8) . . ? N8 O2 C17 110.59(15) . . ? C12 O3 C13 115.35(17) . . ? C10 O7 S1 113.84(12) . . ? C14 N8 O2 119.11(16) . . ? C14 N8 C16 123.42(17) . . ? O2 N8 C16 116.90(16) . . ? C12 N9 C15 126.98(18) . . ? C12 N9 S1 119.89(15) . . ? C15 N9 S1 113.13(14) . . ? O7 C10 C11 109.04(17) . . ? O7 C10 C15 102.58(16) . . ? C11 C10 C15 114.01(17) . . ? O7 C10 C14 102.19(15) . . ? C11 C10 C14 112.83(18) . . ? C15 C10 C14 114.76(17) . . ? C10 C11 H11A 109.7 . . ? C10 C11 H11B 109.5 . . ? H11A C11 H11B 109.5 . . ? C10 C11 H11C 109.3 . . ? H11A C11 H11C 109.5 . . ? H11B C11 H11C 109.5 . . ? O5 C12 O3 126.7(2) . . ? O5 C12 N9 123.1(2) . . ? O3 C12 N9 110.24(17) . . ? O3 C13 H13A 109.5 . . ? O3 C13 H13B 109.2 . . ? H13A C13 H13B 109.5 . . ? O3 C13 H13C 109.7 . . ? H13A C13 H13C 109.5 . . ? H13B C13 H13C 109.5 . . ? O4 C14 N8 121.85(18) . . ? O4 C14 C10 121.22(18) . . ? N8 C14 C10 116.92(17) . . ? N9 C15 C10 103.36(16) . . ? N9 C15 H15A 109.4 . . ? C10 C15 H15A 112.4 . . ? N9 C15 H15B 109.4 . . ? C10 C15 H15B 112.6 . . ? H15A C15 H15B 109.5 . . ? N8 C16 H16A 109.2 . . ? N8 C16 H16B 109.2 . . ? H16A C16 H16B 109.5 . . ? N8 C16 H16C 110.0 . . ? H16A C16 H16C 109.5 . . ? H16B C16 H16C 109.5 . . ? O2 C17 H17A 109.4 . . ? O2 C17 H17B 109.8 . . ? H17A C17 H17B 109.5 . . ? O2 C17 H17C 109.3 . . ? H17A C17 H17C 109.5 . . ? H17B C17 H17C 109.5 . . ? _diffrn_measured_fraction_theta_max 0.968 _diffrn_reflns_theta_full 27.91 _diffrn_measured_fraction_theta_full 0.968 _refine_diff_density_max 0.264 _refine_diff_density_min -0.291 _refine_diff_density_rms 0.055