Supplementary Material (ESI) for Chemical Communications This journal is © The Royal Society of Chemistry 2001 data_global _journal_coden_Cambridge 182 _audit_creation_method SHELXL-97 _publ_contact_author_name 'Prof Dieter Enders' _publ_contact_author_address ; Prof Dieter Enders Institut für Organische Chemie RWTH Aachen Professor-Pirlet-Str.1 Aachen D-52074 GERMANY ; _publ_contact_author_email 'ENDERS@RWTH-AACHEN.DE' _publ_requested_journal 'Chemical Communications' _publ_contact_letter ; This file contains the cif of a new crystal structure for deposition in the Cambridge Data Base. The paper reporting this structure will be submitted to Chemical Communications. ; _publ_section_title ; Diastereo- and Enantioselective Synthesis of a,b-Disubstituted g-Nitro Methyl Sulfonates ; loop_ _publ_author_name _publ_author_address 'Enders, Dieter' ; Institut fur Organische Chemie der RWTH Aachen Professor-Pirlet-Strasse 1 D-52074 Aachen Germany ; 'Berner, Otto Mathias' ; Institut fur Organische Chemie der RWTH Aachen Professor-Pirlet-Strasse 1 D-52074 Aachen Germany ; 'Vignola, Nicola' ; Institut fur Organische Chemie der RWTH Aachen Professor-Pirlet-Strasse 1 D-52074 Aachen Germany ; 'Bats, Jan Willem' ; Institut fur Organische Chemie der Universit\"at Frankfurt Marie-Curie-Strasse 11 D-60439 Frankfurt am Main Germany ; data_compound_2c _database_code_CSD 167504 _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C24 H35 N O10 S' _chemical_formula_sum 'C24 H35 N O10 S' _chemical_formula_weight 529.59 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 212121' 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 9.7493(9) _cell_length_b 15.7940(15) _cell_length_c 17.251(2) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 2656.4(5) _cell_formula_units_Z 4 _cell_measurement_temperature 143(2) _cell_measurement_reflns_used 346 _cell_measurement_theta_min 3 _cell_measurement_theta_max 23 _exptl_crystal_description block _exptl_crystal_colour colorless _exptl_crystal_size_max 0.60 _exptl_crystal_size_mid 0.40 _exptl_crystal_size_min 0.32 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.324 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1128 _exptl_absorpt_coefficient_mu 0.177 _exptl_absorpt_correction_type 'empirical by SADABS (Sheldrick, 2000)' _exptl_absorpt_correction_T_min 0.973 _exptl_absorpt_correction_T_max 1.000 _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 143(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 SIEMENS_SMART_CCD _diffrn_measurement_method \w _diffrn_detector_area_resol_mean ? _diffrn_standards_number 592 _diffrn_standards_interval_count ? _diffrn_standards_interval_time 600 _diffrn_standards_decay_% 0.0 _diffrn_reflns_number 56263 _diffrn_reflns_av_R_equivalents 0.0398 _diffrn_reflns_av_sigmaI/netI 0.0369 _diffrn_reflns_limit_h_min -14 _diffrn_reflns_limit_h_max 14 _diffrn_reflns_limit_k_min -23 _diffrn_reflns_limit_k_max 23 _diffrn_reflns_limit_l_min -24 _diffrn_reflns_limit_l_max 24 _diffrn_reflns_theta_min 1.75 _diffrn_reflns_theta_max 32.55 _reflns_number_total 8871 _reflns_number_gt 7465 _reflns_threshold_expression I>2sigma(I) _computing_data_collection 'SMART (Siemens, 1995)' _computing_cell_refinement 'SMART (Siemens, 1995)' _computing_data_reduction 'SAINT (Siemens, 1995)' _computing_structure_solution 'SHELXS-96 (Sheldrick, 1996)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics ? _computing_publication_material 'CIF in SHELXL-97 (Sheldrick, 1997)' _ccdc_disorder ; The segment containing atoms O9, C22, C23 and C24 was found to be disordered over two possible conformations. Atoms in this group were refined with a split atom model. The occupancy factor of atoms O9, C22, C23 and C24 refined to 0.644(4). The occupancy factor of atoms O9', C22', C23' and C24' was 0.356(4). ; _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^)+(0.06P)^2^] 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 riding _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(5) _refine_ls_number_reflns 8871 _refine_ls_number_parameters 332 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0629 _refine_ls_R_factor_gt 0.0479 _refine_ls_wR_factor_ref 0.1125 _refine_ls_wR_factor_gt 0.1073 _refine_ls_goodness_of_fit_ref 1.220 _refine_ls_restrained_S_all 1.220 _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 S S 0.69350(4) 0.07529(2) 0.95090(2) 0.01876(8) Uani 1 1 d . . . O2 O 0.82361(11) 0.10476(7) 0.97832(7) 0.0264(2) Uani 1 1 d . . . O1 O 0.62514(12) 0.12041(7) 0.89056(7) 0.0266(2) Uani 1 1 d . . . O5 O 0.71056(11) -0.01757(6) 0.91724(7) 0.0225(2) Uani 1 1 d . . . N N 0.49836(14) 0.25884(8) 0.95603(8) 0.0264(3) Uani 1 1 d . . . O10 O 1.14131(12) -0.04462(9) 0.82569(7) 0.0312(3) Uani 1 1 d . . . O6 O 0.99200(12) -0.16399(7) 0.91254(8) 0.0310(3) Uani 1 1 d . A . O4 O 0.60171(13) 0.29254(8) 0.98253(9) 0.0393(3) Uani 1 1 d . . . C5 C 0.31251(18) 0.07894(12) 1.12835(10) 0.0317(3) Uani 1 1 d . . . H5A H 0.2671 0.0719 1.1786 0.048 Uiso 1 1 calc R . . H5B H 0.3366 0.0232 1.1073 0.048 Uiso 1 1 calc R . . H5C H 0.2504 0.1079 1.0924 0.048 Uiso 1 1 calc R . . C2 C 0.52176(15) 0.14614(9) 1.06148(9) 0.0192(3) Uani 1 1 d . . . H2A H 0.6027 0.1832 1.0723 0.023 Uiso 1 1 calc R . . C1 C 0.57525(14) 0.05972(8) 1.02960(8) 0.0170(3) Uani 1 1 d . . . H1A H 0.4942 0.0287 1.0082 0.020 Uiso 1 1 calc R . . O8 O 0.66542(13) -0.18101(8) 0.89748(11) 0.0496(4) Uani 1 1 d . A . O7 O 0.84156(14) -0.27142(10) 0.87820(11) 0.0525(4) Uani 1 1 d . A . O3 O 0.44434(16) 0.27943(9) 0.89512(8) 0.0406(3) Uani 1 1 d . . . C7 C 0.63894(15) 0.00343(9) 1.09113(9) 0.0190(3) Uani 1 1 d . . . C3 C 0.42874(16) 0.19158(9) 1.00308(9) 0.0213(3) Uani 1 1 d . . . H3A H 0.3898 0.1489 0.9673 0.026 Uiso 1 1 calc R . . H3B H 0.3515 0.2177 1.0316 0.026 Uiso 1 1 calc R . . C14 C 0.93167(16) -0.08637(10) 0.88558(10) 0.0236(3) Uani 1 1 d . . . H14A H 0.8897 -0.0958 0.8334 0.028 Uiso 1 1 calc R A . C11 C 0.8011(2) -0.02214(12) 1.19355(11) 0.0353(4) Uani 1 1 d . . . H11A H 0.8774 -0.0042 1.2236 0.042 Uiso 1 1 calc R . . C8 C 0.57891(16) -0.07463(10) 1.10663(9) 0.0238(3) Uani 1 1 d . . . H8A H 0.5023 -0.0928 1.0770 0.029 Uiso 1 1 calc R . . C12 C 0.75142(17) 0.02973(11) 1.13507(10) 0.0269(3) Uani 1 1 d . . . H12A H 0.7936 0.0828 1.1250 0.032 Uiso 1 1 calc R . . C20 C 1.03971(16) -0.01805(10) 0.87981(10) 0.0256(3) Uani 1 1 d . A . H20A H 0.9962 0.0354 0.8609 0.031 Uiso 1 1 calc R . . C21 C 1.12105(17) 0.00063(11) 0.95407(11) 0.0301(3) Uani 1 1 d . . . H21A H 1.1104 -0.0446 0.9908 0.040 Uiso 0.644(4) 1 d P . . H21B H 1.0891 0.0522 0.9777 0.040 Uiso 0.644(4) 1 d P . . C9 C 0.6303(2) -0.12647(11) 1.16534(11) 0.0332(4) Uani 1 1 d . . . H9A H 0.5890 -0.1799 1.1753 0.040 Uiso 1 1 calc R . . C4 C 0.44320(17) 0.13180(10) 1.13878(9) 0.0252(3) Uani 1 1 d . . . H4A H 0.5055 0.0995 1.1741 0.030 Uiso 1 1 calc R . . C15 C 0.88576(17) -0.21829(10) 0.93755(11) 0.0290(4) Uani 1 1 d . . . H15A H 0.9148 -0.2517 0.9839 0.035 Uiso 1 1 calc R A . C18 C 0.6160(3) -0.32907(13) 0.88567(16) 0.0538(6) Uani 1 1 d . A . H18A H 0.6255 -0.3351 0.9420 0.081 Uiso 1 1 calc R . . H18B H 0.6459 -0.3814 0.8602 0.081 Uiso 1 1 calc R . . H18C H 0.5198 -0.3180 0.8727 0.081 Uiso 1 1 calc R . . C10 C 0.7406(2) -0.10020(12) 1.20875(11) 0.0376(4) Uani 1 1 d . . . H10A H 0.7754 -0.1352 1.2490 0.045 Uiso 1 1 calc R . . C17 C 0.7029(2) -0.25684(12) 0.85830(12) 0.0376(4) Uani 1 1 d . . . C16 C 0.76124(17) -0.16284(10) 0.95626(11) 0.0295(4) Uani 1 1 d . A . H16A H 0.7241 -0.1730 1.0095 0.035 Uiso 1 1 calc R . . C13 C 0.81766(15) -0.07313(9) 0.94561(9) 0.0226(3) Uani 1 1 d . A . H13A H 0.8564 -0.0512 0.9954 0.027 Uiso 1 1 calc R . . C6 C 0.4107(3) 0.21615(13) 1.17843(12) 0.0443(5) Uani 1 1 d . . . H6A H 0.3609 0.2055 1.2268 0.067 Uiso 1 1 calc R . . H6B H 0.3540 0.2509 1.1440 0.067 Uiso 1 1 calc R . . H6C H 0.4964 0.2461 1.1899 0.067 Uiso 1 1 calc R . . C19 C 0.6908(5) -0.2430(3) 0.77205(17) 0.1004(13) Uani 1 1 d . A . H19A H 0.7474 -0.1945 0.7568 0.151 Uiso 1 1 calc R . . H19B H 0.5948 -0.2318 0.7587 0.151 Uiso 1 1 calc R . . H19C H 0.7223 -0.2937 0.7446 0.151 Uiso 1 1 calc R . . O9 O 1.2600(2) 0.00807(16) 0.93116(13) 0.0353(6) Uiso 0.644(4) 1 d P A 1 C22 C 1.2737(3) -0.0482(2) 0.86194(18) 0.0258(6) Uiso 0.644(4) 1 d P A 1 C23 C 1.3756(4) 0.0031(3) 0.8163(2) 0.0649(14) Uani 0.644(4) 1 d P A 1 H23A H 1.3972 -0.0263 0.7678 0.097 Uiso 0.644(4) 1 calc PR A 1 H23B H 1.4596 0.0103 0.8467 0.097 Uiso 0.644(4) 1 calc PR A 1 H23C H 1.3363 0.0588 0.8045 0.097 Uiso 0.644(4) 1 calc PR A 1 C24 C 1.3164(4) -0.1349(3) 0.8771(4) 0.087(2) Uani 0.644(4) 1 d P A 1 H24A H 1.2448 -0.1641 0.9067 0.130 Uiso 0.644(4) 1 calc PR A 1 H24B H 1.4018 -0.1346 0.9070 0.130 Uiso 0.644(4) 1 calc PR A 1 H24C H 1.3312 -0.1644 0.8279 0.130 Uiso 0.644(4) 1 calc PR A 1 O9' O 1.2503(3) -0.0355(3) 0.93952(19) 0.0268(9) Uiso 0.356(4) 1 d P A 2 C22' C 1.2709(5) -0.0212(4) 0.8545(3) 0.0220(11) Uiso 0.356(4) 1 d P A 2 C23' C 1.3053(10) 0.0602(6) 0.8215(5) 0.069(2) Uiso 0.356(4) 1 d P A 2 C24' C 1.3719(9) -0.0947(6) 0.8376(5) 0.066(2) Uiso 0.356(4) 1 d P A 2 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 0.01841(15) 0.01671(14) 0.02115(17) -0.00055(13) 0.00370(14) 0.00103(13) O2 0.0201(5) 0.0242(5) 0.0349(6) -0.0030(5) 0.0047(5) -0.0049(4) O1 0.0309(6) 0.0261(5) 0.0228(6) 0.0053(5) 0.0064(5) 0.0085(5) O5 0.0208(5) 0.0198(5) 0.0270(6) -0.0062(4) -0.0019(4) 0.0049(4) N 0.0273(6) 0.0205(6) 0.0313(7) 0.0038(6) 0.0081(6) 0.0059(5) O10 0.0193(5) 0.0498(8) 0.0245(6) -0.0078(5) 0.0018(5) 0.0023(5) O6 0.0222(5) 0.0228(6) 0.0480(8) -0.0035(5) 0.0009(5) 0.0061(4) O4 0.0280(6) 0.0283(6) 0.0616(9) 0.0081(6) 0.0065(6) -0.0036(5) C5 0.0274(8) 0.0404(9) 0.0273(8) 0.0076(7) 0.0085(7) 0.0032(8) C2 0.0203(6) 0.0173(6) 0.0201(7) -0.0019(5) 0.0004(5) 0.0016(5) C1 0.0147(6) 0.0173(6) 0.0191(7) 0.0008(5) 0.0010(5) -0.0004(5) O8 0.0275(7) 0.0262(6) 0.0951(13) -0.0075(7) -0.0202(7) 0.0026(5) O7 0.0322(7) 0.0461(8) 0.0791(11) -0.0363(8) -0.0065(7) 0.0041(6) O3 0.0532(8) 0.0377(7) 0.0307(7) 0.0103(6) 0.0041(6) 0.0156(6) C7 0.0205(7) 0.0181(6) 0.0185(7) -0.0003(5) 0.0006(6) 0.0005(5) C3 0.0195(7) 0.0197(6) 0.0248(8) 0.0024(6) 0.0018(6) 0.0014(5) C14 0.0204(7) 0.0239(7) 0.0264(8) -0.0051(6) 0.0003(6) 0.0038(6) C11 0.0334(9) 0.0417(9) 0.0307(9) 0.0025(7) -0.0138(8) 0.0007(8) C8 0.0266(7) 0.0206(6) 0.0240(7) 0.0018(6) -0.0009(6) -0.0024(6) C12 0.0239(7) 0.0262(7) 0.0305(9) 0.0019(7) -0.0049(7) -0.0018(6) C20 0.0203(7) 0.0272(7) 0.0292(9) -0.0029(7) 0.0028(6) 0.0024(6) C21 0.0254(8) 0.0350(8) 0.0301(9) -0.0079(8) -0.0007(7) -0.0022(7) C9 0.0425(10) 0.0276(8) 0.0295(9) 0.0085(7) -0.0006(8) -0.0016(7) C4 0.0293(8) 0.0284(8) 0.0179(7) -0.0022(6) 0.0019(6) 0.0073(6) C15 0.0285(8) 0.0206(7) 0.0378(10) -0.0019(7) -0.0018(7) 0.0053(6) C18 0.0532(13) 0.0350(10) 0.0731(16) -0.0092(11) 0.0204(12) -0.0169(10) C10 0.0453(11) 0.0378(9) 0.0297(10) 0.0120(8) -0.0073(8) 0.0055(8) C17 0.0376(10) 0.0323(9) 0.0430(10) 0.0004(8) -0.0082(9) -0.0085(8) C16 0.0270(8) 0.0216(7) 0.0398(10) 0.0001(7) 0.0073(7) 0.0029(6) C13 0.0216(7) 0.0207(6) 0.0257(7) -0.0029(6) 0.0009(6) 0.0065(6) C6 0.0634(14) 0.0374(10) 0.0322(10) -0.0123(8) 0.0103(9) 0.0131(10) C19 0.151(3) 0.099(2) 0.0512(16) 0.0253(16) -0.026(2) -0.054(3) C23 0.0328(18) 0.109(4) 0.053(2) 0.006(2) -0.0094(16) -0.033(2) C24 0.0287(18) 0.056(2) 0.175(6) 0.016(3) -0.037(3) 0.0103(17) _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 1.4267(12) . ? S O2 1.4316(12) . ? S O5 1.5861(11) . ? S C1 1.7980(14) . ? O5 C13 1.4491(17) . ? N O3 1.2195(19) . ? N O4 1.2278(19) . ? N C3 1.4993(19) . ? O10 C22' 1.407(5) . ? O10 C20 1.4244(19) . ? O10 C22 1.436(3) . ? O6 C15 1.412(2) . ? O6 C14 1.4371(19) . ? C5 C4 1.534(2) . ? C2 C3 1.534(2) . ? C2 C4 1.555(2) . ? C2 C1 1.5613(19) . ? C1 C7 1.517(2) . ? O8 C16 1.408(2) . ? O8 C17 1.423(2) . ? O7 C15 1.392(2) . ? O7 C17 1.414(2) . ? C7 C8 1.391(2) . ? C7 C12 1.396(2) . ? C14 C20 1.511(2) . ? C14 C13 1.534(2) . ? C11 C12 1.387(2) . ? C11 C10 1.392(3) . ? C8 C9 1.395(2) . ? C20 C21 1.535(2) . ? C21 O9' 1.406(4) . ? C21 O9 1.416(3) . ? C9 C10 1.375(3) . ? C4 C6 1.531(2) . ? C15 C16 1.531(2) . ? C18 C17 1.497(3) . ? C17 C19 1.509(3) . ? C16 C13 1.531(2) . ? O9 C22 1.495(4) . ? C22 C24 1.455(5) . ? C22 C23 1.505(5) . ? O9' C22' 1.498(6) . ? C22' C23' 1.446(10) . ? C22' C24' 1.549(10) . ? 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 119.51(7) . . ? O1 S O5 104.11(7) . . ? O2 S O5 109.19(6) . . ? O1 S C1 108.65(7) . . ? O2 S C1 111.29(7) . . ? O5 S C1 102.54(6) . . ? C13 O5 S 120.78(10) . . ? O3 N O4 124.03(15) . . ? O3 N C3 117.38(14) . . ? O4 N C3 118.49(14) . . ? C22' O10 C20 108.4(2) . . ? C22' O10 C22 18.0(2) . . ? C20 O10 C22 110.58(15) . . ? C15 O6 C14 108.47(12) . . ? C3 C2 C4 109.90(12) . . ? C3 C2 C1 112.04(12) . . ? C4 C2 C1 109.83(12) . . ? C7 C1 C2 113.74(12) . . ? C7 C1 S 110.24(10) . . ? C2 C1 S 111.13(9) . . ? C16 O8 C17 110.07(13) . . ? C15 O7 C17 112.11(15) . . ? C8 C7 C12 119.33(14) . . ? C8 C7 C1 118.80(13) . . ? C12 C7 C1 121.79(13) . . ? N C3 C2 114.80(12) . . ? O6 C14 C20 110.19(13) . . ? O6 C14 C13 101.21(12) . . ? C20 C14 C13 116.89(13) . . ? C12 C11 C10 120.81(17) . . ? C7 C8 C9 120.59(15) . . ? C11 C12 C7 119.57(16) . . ? O10 C20 C14 108.51(13) . . ? O10 C20 C21 104.14(13) . . ? C14 C20 C21 116.26(14) . . ? O9' C21 O9 29.11(14) . . ? O9' C21 C20 103.66(18) . . ? O9 C21 C20 106.10(16) . . ? C10 C9 C8 119.94(17) . . ? C6 C4 C5 110.75(15) . . ? C6 C4 C2 111.00(14) . . ? C5 C4 C2 112.83(13) . . ? O7 C15 O6 111.61(16) . . ? O7 C15 C16 104.73(14) . . ? O6 C15 C16 107.37(12) . . ? C9 C10 C11 119.76(17) . . ? O7 C17 O8 105.50(15) . . ? O7 C17 C18 109.90(18) . . ? O8 C17 C18 110.25(18) . . ? O7 C17 C19 109.8(3) . . ? O8 C17 C19 109.1(2) . . ? C18 C17 C19 112.2(2) . . ? O8 C16 C13 109.91(14) . . ? O8 C16 C15 104.93(14) . . ? C13 C16 C15 102.66(13) . . ? O5 C13 C16 110.00(12) . . ? O5 C13 C14 112.13(13) . . ? C16 C13 C14 102.43(12) . . ? C21 O9 C22 105.0(2) . . ? O10 C22 C24 111.9(3) . . ? O10 C22 O9 104.1(2) . . ? C24 C22 O9 116.2(4) . . ? O10 C22 C23 110.1(3) . . ? C24 C22 C23 114.4(4) . . ? O9 C22 C23 99.0(3) . . ? C21 O9' C22' 103.5(3) . . ? O10 C22' C23' 107.7(5) . . ? O10 C22' O9' 100.7(4) . . ? C23' C22' O9' 123.4(5) . . ? O10 C22' C24' 107.9(5) . . ? C23' C22' C24' 116.4(6) . . ? O9' C22' C24' 99.0(5) . . ? 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 O1 S O5 C13 155.93(11) . . . . ? O2 S O5 C13 27.23(13) . . . . ? C1 S O5 C13 -90.89(12) . . . . ? C3 C2 C1 C7 -166.34(12) . . . . ? C4 C2 C1 C7 -43.90(16) . . . . ? C3 C2 C1 S 68.55(14) . . . . ? C4 C2 C1 S -169.01(10) . . . . ? O1 S C1 C7 173.64(10) . . . . ? O2 S C1 C7 -52.78(12) . . . . ? O5 S C1 C7 63.84(11) . . . . ? O1 S C1 C2 -59.31(11) . . . . ? O2 S C1 C2 74.27(11) . . . . ? O5 S C1 C2 -169.11(10) . . . . ? C2 C1 C7 C8 117.70(15) . . . . ? S C1 C7 C8 -116.71(13) . . . . ? C2 C1 C7 C12 -58.98(19) . . . . ? S C1 C7 C12 66.61(17) . . . . ? O3 N C3 C2 159.13(13) . . . . ? O4 N C3 C2 -24.30(19) . . . . ? C4 C2 C3 N 139.38(13) . . . . ? C1 C2 C3 N -98.22(15) . . . . ? C15 O6 C14 C20 163.97(14) . . . . ? C15 O6 C14 C13 39.62(15) . . . . ? C12 C7 C8 C9 -0.1(2) . . . . ? C1 C7 C8 C9 -176.86(15) . . . . ? C10 C11 C12 C7 0.3(3) . . . . ? C8 C7 C12 C11 -0.2(2) . . . . ? C1 C7 C12 C11 176.42(15) . . . . ? C22' O10 C20 C14 -140.1(3) . . . . ? C22 O10 C20 C14 -121.09(19) . . . . ? C22' O10 C20 C21 -15.6(3) . . . . ? C22 O10 C20 C21 3.3(2) . . . . ? O6 C14 C20 O10 60.86(17) . . . . ? C13 C14 C20 O10 175.62(13) . . . . ? O6 C14 C20 C21 -56.04(18) . . . . ? C13 C14 C20 C21 58.71(18) . . . . ? O10 C20 C21 O9' -13.2(2) . . . . ? C14 C20 C21 O9' 106.1(2) . . . . ? O10 C20 C21 O9 16.89(19) . . . . ? C14 C20 C21 O9 136.19(17) . . . . ? C7 C8 C9 C10 0.4(3) . . . . ? C3 C2 C4 C6 -65.93(18) . . . . ? C1 C2 C4 C6 170.38(14) . . . . ? C3 C2 C4 C5 59.06(17) . . . . ? C1 C2 C4 C5 -64.64(16) . . . . ? C17 O7 C15 O6 -116.90(17) . . . . ? C17 O7 C15 C16 -1.0(2) . . . . ? C14 O6 C15 O7 92.13(16) . . . . ? C14 O6 C15 C16 -22.10(18) . . . . ? C8 C9 C10 C11 -0.4(3) . . . . ? C12 C11 C10 C9 0.0(3) . . . . ? C15 O7 C17 O8 10.5(2) . . . . ? C15 O7 C17 C18 -108.4(2) . . . . ? C15 O7 C17 C19 127.9(2) . . . . ? C16 O8 C17 O7 -16.5(2) . . . . ? C16 O8 C17 C18 102.1(2) . . . . ? C16 O8 C17 C19 -134.3(2) . . . . ? C17 O8 C16 C13 125.50(16) . . . . ? C17 O8 C16 C15 15.76(19) . . . . ? O7 C15 C16 O8 -8.90(19) . . . . ? O6 C15 C16 O8 109.87(15) . . . . ? O7 C15 C16 C13 -123.81(16) . . . . ? O6 C15 C16 C13 -5.04(18) . . . . ? S O5 C13 C16 137.92(12) . . . . ? S O5 C13 C14 -108.80(13) . . . . ? O8 C16 C13 O5 36.05(18) . . . . ? C15 C16 C13 O5 147.29(13) . . . . ? O8 C16 C13 C14 -83.34(15) . . . . ? C15 C16 C13 C14 27.90(16) . . . . ? O6 C14 C13 O5 -158.87(12) . . . . ? C20 C14 C13 O5 81.46(17) . . . . ? O6 C14 C13 C16 -40.98(15) . . . . ? C20 C14 C13 C16 -160.66(14) . . . . ? O9' C21 O9 C22 59.6(4) . . . . ? C20 C21 O9 C22 -29.6(3) . . . . ? C22' O10 C22 C24 -168.5(11) . . . . ? C20 O10 C22 C24 105.1(4) . . . . ? C22' O10 C22 O9 65.2(9) . . . . ? C20 O10 C22 O9 -21.1(3) . . . . ? C22' O10 C22 C23 -40.1(9) . . . . ? C20 O10 C22 C23 -126.5(3) . . . . ? C21 O9 C22 O10 31.5(3) . . . . ? C21 O9 C22 C24 -92.0(3) . . . . ? C21 O9 C22 C23 145.0(3) . . . . ? O9 C21 O9' C22' -63.7(4) . . . . ? C20 C21 O9' C22' 35.0(4) . . . . ? C20 O10 C22' C23' -93.9(5) . . . . ? C22 O10 C22' C23' 166.1(12) . . . . ? C20 O10 C22' O9' 36.5(4) . . . . ? C22 O10 C22' O9' -63.6(8) . . . . ? C20 O10 C22' C24' 139.7(4) . . . . ? C22 O10 C22' C24' 39.7(8) . . . . ? C21 O9' C22' O10 -44.7(4) . . . . ? C21 O9' C22' C23' 74.9(6) . . . . ? C21 O9' C22' C24' -155.0(4) . . . . ? _diffrn_measured_fraction_theta_max 0.950 _diffrn_reflns_theta_full 32.55 _diffrn_measured_fraction_theta_full 0.950 _refine_diff_density_max 0.543 _refine_diff_density_min -0.340 _refine_diff_density_rms 0.054