Supplementary Material (ESI) for Chemical Communications This journal is (c) The Royal Society of Chemistry 2003 data_global _journal_coden_Cambridge 182 loop_ _publ_author_name 'Stuart Warren' 'Lorenzo Caggiano' 'John Davies' 'David J. Fox' 'David C. Moody' _publ_contact_author_name 'Dr Stuart Warren' _publ_contact_author_address ; University Chemical Laboratories Cambridge University Lensfield Road Cambridge Cambs CB2 1EW UNITED KINGDOM ; _publ_contact_author_email SW134@CAM.AC.UK _publ_requested_journal 'Chemical Communications' _publ_section_title ; Stereoselective substituted pyrrolidine and cyclic ether synthesis by PhS migration ; data_sw0102 _database_code_CSD 207753 _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C17 H23 N O2 S' _chemical_formula_weight 305.42 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 Monoclinic _symmetry_space_group_name_H-M P2(1)/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 8.5716(4) _cell_length_b 6.5783(2) _cell_length_c 28.464(2) _cell_angle_alpha 90.00 _cell_angle_beta 92.190(2) _cell_angle_gamma 90.00 _cell_volume 1603.84(15) _cell_formula_units_Z 4 _cell_measurement_temperature 180(2) _cell_measurement_reflns_used 9025 _cell_measurement_theta_min 1.0 _cell_measurement_theta_max 27.48 _exptl_crystal_description ? _exptl_crystal_colour colourless _exptl_crystal_size_max 0.23 _exptl_crystal_size_mid 0.18 _exptl_crystal_size_min 0.16 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.265 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 656 _exptl_absorpt_coefficient_mu 0.206 _exptl_absorpt_correction_type multiscan _exptl_absorpt_correction_T_max 1.000 _exptl_absorpt_correction_T_min 0.979 _exptl_absorpt_process_details ; Sortav Blessing (1995) multi-scan from symmetry-related measurements (Blessing 1995) ; _exptl_special_details ; ? ; _diffrn_ambient_temperature 180(2) _diffrn_radiation_wavelength 0.71069 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_measurement_device_type KappaCCD _diffrn_measurement_device '95mm CCD camera on \k-goniostat' _diffrn_detector_area_resol_mean 9 _diffrn_radiation_monochromator 'horizonally mounted graphite crystal' _diffrn_measurement_method CCD _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 9478 _diffrn_reflns_av_R_equivalents 0.0441 _diffrn_reflns_av_sigmaI/netI 0.0565 _diffrn_reflns_limit_h_min -11 _diffrn_reflns_limit_h_max 11 _diffrn_reflns_limit_k_min -8 _diffrn_reflns_limit_k_max 8 _diffrn_reflns_limit_l_min -24 _diffrn_reflns_limit_l_max 36 _diffrn_reflns_theta_min 3.77 _diffrn_reflns_theta_max 27.48 _reflns_number_total 3642 _reflns_number_gt 2707 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Collect (Nonius BV, 1997-2000)' _computing_cell_refinement 'HKL Scalepack (Otwinowski & Minor 1997)' _computing_data_reduction ; HKL Denzo and Scalepack (Otwinowski & Minor 1997) ; _computing_structure_solution teXsan _computing_structure_refinement 'SHELXL-93 (Sheldrick, 1993)' _computing_molecular_graphics ? _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^)+(0.0475P)^2^+0.1524P] 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 3642 _refine_ls_number_parameters 191 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0615 _refine_ls_R_factor_gt 0.0417 _refine_ls_wR_factor_ref 0.1068 _refine_ls_wR_factor_gt 0.0981 _refine_ls_goodness_of_fit_ref 1.049 _refine_ls_restrained_S_all 1.049 _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 0.45215(5) 0.48241(6) 0.872091(14) 0.03003(13) Uani 1 1 d . . . O1 O 0.80783(12) 0.07753(14) 0.89445(3) 0.0241(2) Uani 1 1 d . . . O2 O 0.91863(13) -0.12105(14) 0.94832(4) 0.0294(3) Uani 1 1 d . . . N1 N 0.92515(15) 0.21766(17) 0.96144(4) 0.0275(3) Uani 1 1 d . . . H1 H 0.9820 0.1976 0.9874 0.033 Uiso 1 1 calc R . . C1 C 0.88543(18) 0.0533(2) 0.93647(5) 0.0231(3) Uani 1 1 d . . . C2 C 0.8841(2) 0.4274(2) 0.95015(5) 0.0291(4) Uani 1 1 d . . . H2A H 0.9759 0.5158 0.9566 0.035 Uiso 1 1 calc R . . H2B H 0.7997 0.4727 0.9705 0.035 Uiso 1 1 calc R . . C3 C 0.83016(18) 0.4495(2) 0.89879(5) 0.0257(3) Uani 1 1 d . . . H3 H 0.7651 0.5753 0.8958 0.031 Uiso 1 1 calc R . . C4 C 0.73015(17) 0.26947(19) 0.88183(5) 0.0226(3) Uani 1 1 d . . . H4 H 0.7295 0.2757 0.8467 0.027 Uiso 1 1 calc R . . C5 C 0.9705(2) 0.4747(3) 0.86792(6) 0.0375(4) Uani 1 1 d . . . H5A H 1.0290 0.5966 0.8776 0.056 Uiso 1 1 calc R . . H5B H 0.9343 0.4884 0.8350 0.056 Uiso 1 1 calc R . . H5C H 1.0383 0.3552 0.8713 0.056 Uiso 1 1 calc R . . C6 C 0.55657(18) 0.2523(2) 0.89439(5) 0.0235(3) Uani 1 1 d . . . C7 C 0.48851(18) 0.0572(2) 0.87182(5) 0.0264(3) Uani 1 1 d . . . H7A H 0.4906 0.0705 0.8372 0.032 Uiso 1 1 calc R . . H7B H 0.5565 -0.0587 0.8812 0.032 Uiso 1 1 calc R . . C8 C 0.3221(2) 0.0094(2) 0.88521(6) 0.0329(4) Uani 1 1 d . . . H8A H 0.2507 0.1162 0.8727 0.039 Uiso 1 1 calc R . . H8B H 0.2891 -0.1221 0.8711 0.039 Uiso 1 1 calc R . . C9 C 0.3124(2) -0.0015(3) 0.93822(6) 0.0396(4) Uani 1 1 d . . . H9A H 0.3803 -0.1126 0.9506 0.048 Uiso 1 1 calc R . . H9B H 0.2038 -0.0319 0.9465 0.048 Uiso 1 1 calc R . . C10 C 0.3636(2) 0.1986(3) 0.96047(6) 0.0375(4) Uani 1 1 d . . . H10A H 0.3587 0.1880 0.9951 0.045 Uiso 1 1 calc R . . H10B H 0.2911 0.3077 0.9497 0.045 Uiso 1 1 calc R . . C11 C 0.52995(19) 0.2541(2) 0.94752(5) 0.0295(4) Uani 1 1 d . . . H11A H 0.6035 0.1572 0.9631 0.035 Uiso 1 1 calc R . . H11B H 0.5547 0.3914 0.9600 0.035 Uiso 1 1 calc R . . C12 C 0.4787(2) 0.4771(2) 0.81036(6) 0.0312(4) Uani 1 1 d . . . C13 C 0.3792(2) 0.3668(3) 0.78044(6) 0.0457(5) Uani 1 1 d . . . H13 H 0.2954 0.2921 0.7929 0.055 Uiso 1 1 calc R . . C14 C 0.4013(3) 0.3648(3) 0.73249(7) 0.0583(6) Uani 1 1 d . . . H14 H 0.3339 0.2870 0.7123 0.070 Uiso 1 1 calc R . . C15 C 0.5210(3) 0.4756(3) 0.71406(7) 0.0590(6) Uani 1 1 d . . . H15 H 0.5366 0.4737 0.6812 0.071 Uiso 1 1 calc R . . C16 C 0.6181(3) 0.5890(3) 0.74357(7) 0.0549(5) Uani 1 1 d . . . H16 H 0.6998 0.6667 0.7308 0.066 Uiso 1 1 calc R . . C17 C 0.5979(2) 0.5911(3) 0.79137(6) 0.0409(4) Uani 1 1 d . . . H17 H 0.6652 0.6702 0.8114 0.049 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 0.0348(2) 0.0244(2) 0.0309(2) 0.00375(15) 0.00204(18) 0.00928(17) O1 0.0285(6) 0.0182(5) 0.0251(6) -0.0026(4) -0.0035(4) 0.0059(4) O2 0.0352(7) 0.0160(5) 0.0364(6) 0.0016(4) -0.0059(5) 0.0016(4) N1 0.0380(8) 0.0173(6) 0.0263(7) 0.0003(5) -0.0093(6) 0.0012(5) C1 0.0233(8) 0.0210(8) 0.0250(8) 0.0005(6) 0.0008(6) 0.0018(6) C2 0.0393(10) 0.0159(7) 0.0315(9) -0.0001(6) -0.0067(7) 0.0034(6) C3 0.0309(9) 0.0187(7) 0.0274(8) 0.0023(6) -0.0022(7) 0.0017(6) C4 0.0293(9) 0.0185(7) 0.0198(8) 0.0019(5) -0.0005(6) 0.0053(6) C5 0.0352(10) 0.0374(9) 0.0399(11) 0.0062(7) 0.0009(8) -0.0053(8) C6 0.0296(9) 0.0209(7) 0.0199(8) 0.0020(5) 0.0005(6) 0.0047(6) C7 0.0305(9) 0.0212(7) 0.0273(8) 0.0009(6) -0.0009(7) 0.0023(6) C8 0.0276(9) 0.0287(8) 0.0420(10) 0.0059(7) -0.0037(7) 0.0014(7) C9 0.0291(10) 0.0436(10) 0.0465(11) 0.0143(8) 0.0076(8) 0.0001(8) C10 0.0356(10) 0.0454(10) 0.0320(10) 0.0082(7) 0.0095(8) 0.0074(8) C11 0.0350(10) 0.0309(8) 0.0227(8) 0.0010(6) 0.0020(7) 0.0032(7) C12 0.0352(9) 0.0274(8) 0.0307(9) 0.0096(6) -0.0023(7) 0.0070(7) C13 0.0524(12) 0.0470(11) 0.0367(10) 0.0121(8) -0.0109(9) -0.0069(9) C14 0.0822(17) 0.0576(13) 0.0334(11) 0.0083(9) -0.0193(11) -0.0124(12) C15 0.0876(18) 0.0610(13) 0.0283(11) 0.0113(9) 0.0021(11) 0.0056(12) C16 0.0646(14) 0.0611(13) 0.0394(11) 0.0203(10) 0.0074(10) -0.0034(11) C17 0.0494(12) 0.0367(9) 0.0366(10) 0.0126(8) -0.0009(9) -0.0007(8) _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 C12 1.7807(17) . ? S1 C6 1.8577(14) . ? O1 C1 1.3556(17) . ? O1 C4 1.4657(16) . ? O2 C1 1.2261(16) . ? N1 C1 1.3309(18) . ? N1 C2 1.4570(18) . ? N1 H1 0.8800 . ? C2 C3 1.523(2) . ? C2 H2A 0.9900 . ? C2 H2B 0.9900 . ? C3 C5 1.525(2) . ? C3 C4 1.529(2) . ? C3 H3 1.0000 . ? C4 C6 1.548(2) . ? C4 H4 1.0000 . ? C5 H5A 0.9800 . ? C5 H5B 0.9800 . ? C5 H5C 0.9800 . ? C6 C11 1.538(2) . ? C6 C7 1.540(2) . ? C7 C8 1.523(2) . ? C7 H7A 0.9900 . ? C7 H7B 0.9900 . ? C8 C9 1.516(2) . ? C8 H8A 0.9900 . ? C8 H8B 0.9900 . ? C9 C10 1.518(2) . ? C9 H9A 0.9900 . ? C9 H9B 0.9900 . ? C10 C11 1.531(2) . ? C10 H10A 0.9900 . ? C10 H10B 0.9900 . ? C11 H11A 0.9900 . ? C11 H11B 0.9900 . ? C12 C13 1.387(2) . ? C12 C17 1.393(2) . ? C13 C14 1.385(3) . ? C13 H13 0.9500 . ? C14 C15 1.378(3) . ? C14 H14 0.9500 . ? C15 C16 1.379(3) . ? C15 H15 0.9500 . ? C16 C17 1.378(2) . ? C16 H16 0.9500 . ? C17 H17 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 C12 S1 C6 104.08(7) . . ? C1 O1 C4 121.36(10) . . ? C1 N1 C2 126.64(13) . . ? C1 N1 H1 116.7 . . ? C2 N1 H1 116.7 . . ? O2 C1 N1 124.13(14) . . ? O2 C1 O1 116.97(12) . . ? N1 C1 O1 118.87(12) . . ? N1 C2 C3 111.33(11) . . ? N1 C2 H2A 109.4 . . ? C3 C2 H2A 109.4 . . ? N1 C2 H2B 109.4 . . ? C3 C2 H2B 109.4 . . ? H2A C2 H2B 108.0 . . ? C2 C3 C5 110.25(14) . . ? C2 C3 C4 112.04(11) . . ? C5 C3 C4 110.31(13) . . ? C2 C3 H3 108.0 . . ? C5 C3 H3 108.0 . . ? C4 C3 H3 108.0 . . ? O1 C4 C3 110.23(11) . . ? O1 C4 C6 108.20(10) . . ? C3 C4 C6 121.05(12) . . ? O1 C4 H4 105.4 . . ? C3 C4 H4 105.4 . . ? C6 C4 H4 105.4 . . ? C3 C5 H5A 109.5 . . ? C3 C5 H5B 109.5 . . ? H5A C5 H5B 109.5 . . ? C3 C5 H5C 109.5 . . ? H5A C5 H5C 109.5 . . ? H5B C5 H5C 109.5 . . ? C11 C6 C7 110.39(12) . . ? C11 C6 C4 113.99(12) . . ? C7 C6 C4 108.46(11) . . ? C11 C6 S1 104.00(9) . . ? C7 C6 S1 111.51(10) . . ? C4 C6 S1 108.46(9) . . ? C8 C7 C6 114.29(13) . . ? C8 C7 H7A 108.7 . . ? C6 C7 H7A 108.7 . . ? C8 C7 H7B 108.7 . . ? C6 C7 H7B 108.7 . . ? H7A C7 H7B 107.6 . . ? C9 C8 C7 110.27(13) . . ? C9 C8 H8A 109.6 . . ? C7 C8 H8A 109.6 . . ? C9 C8 H8B 109.6 . . ? C7 C8 H8B 109.6 . . ? H8A C8 H8B 108.1 . . ? C8 C9 C10 110.38(13) . . ? C8 C9 H9A 109.6 . . ? C10 C9 H9A 109.6 . . ? C8 C9 H9B 109.6 . . ? C10 C9 H9B 109.6 . . ? H9A C9 H9B 108.1 . . ? C9 C10 C11 111.32(14) . . ? C9 C10 H10A 109.4 . . ? C11 C10 H10A 109.4 . . ? C9 C10 H10B 109.4 . . ? C11 C10 H10B 109.4 . . ? H10A C10 H10B 108.0 . . ? C10 C11 C6 114.18(13) . . ? C10 C11 H11A 108.7 . . ? C6 C11 H11A 108.7 . . ? C10 C11 H11B 108.7 . . ? C6 C11 H11B 108.7 . . ? H11A C11 H11B 107.6 . . ? C13 C12 C17 119.10(16) . . ? C13 C12 S1 121.16(13) . . ? C17 C12 S1 119.70(13) . . ? C14 C13 C12 120.37(18) . . ? C14 C13 H13 119.8 . . ? C12 C13 H13 119.8 . . ? C15 C14 C13 120.14(19) . . ? C15 C14 H14 119.9 . . ? C13 C14 H14 119.9 . . ? C14 C15 C16 119.66(18) . . ? C14 C15 H15 120.2 . . ? C16 C15 H15 120.2 . . ? C17 C16 C15 120.75(19) . . ? C17 C16 H16 119.6 . . ? C15 C16 H16 119.6 . . ? C16 C17 C12 119.95(18) . . ? C16 C17 H17 120.0 . . ? C12 C17 H17 120.0 . . ? 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 C2 N1 C1 O2 -177.44(15) . . . . ? C2 N1 C1 O1 4.8(2) . . . . ? C4 O1 C1 O2 165.21(12) . . . . ? C4 O1 C1 N1 -16.9(2) . . . . ? C1 N1 C2 C3 -17.1(2) . . . . ? N1 C2 C3 C5 -84.41(16) . . . . ? N1 C2 C3 C4 38.85(18) . . . . ? C1 O1 C4 C3 39.54(17) . . . . ? C1 O1 C4 C6 -94.86(14) . . . . ? C2 C3 C4 O1 -49.46(16) . . . . ? C5 C3 C4 O1 73.77(15) . . . . ? C2 C3 C4 C6 78.15(16) . . . . ? C5 C3 C4 C6 -158.62(13) . . . . ? O1 C4 C6 C11 71.30(14) . . . . ? C3 C4 C6 C11 -57.22(16) . . . . ? O1 C4 C6 C7 -52.12(14) . . . . ? C3 C4 C6 C7 179.37(12) . . . . ? O1 C4 C6 S1 -173.38(9) . . . . ? C3 C4 C6 S1 58.11(15) . . . . ? C12 S1 C6 C11 -178.59(10) . . . . ? C12 S1 C6 C7 -59.62(12) . . . . ? C12 S1 C6 C4 59.74(11) . . . . ? C11 C6 C7 C8 48.75(17) . . . . ? C4 C6 C7 C8 174.30(12) . . . . ? S1 C6 C7 C8 -66.34(15) . . . . ? C6 C7 C8 C9 -55.53(17) . . . . ? C7 C8 C9 C10 58.93(17) . . . . ? C8 C9 C10 C11 -57.85(18) . . . . ? C9 C10 C11 C6 52.75(18) . . . . ? C7 C6 C11 C10 -47.03(17) . . . . ? C4 C6 C11 C10 -169.39(12) . . . . ? S1 C6 C11 C10 72.70(14) . . . . ? C6 S1 C12 C13 85.46(15) . . . . ? C6 S1 C12 C17 -96.78(14) . . . . ? C17 C12 C13 C14 2.1(3) . . . . ? S1 C12 C13 C14 179.84(15) . . . . ? C12 C13 C14 C15 -1.1(3) . . . . ? C13 C14 C15 C16 -0.3(3) . . . . ? C14 C15 C16 C17 0.8(3) . . . . ? C15 C16 C17 C12 0.2(3) . . . . ? C13 C12 C17 C16 -1.6(2) . . . . ? S1 C12 C17 C16 -179.43(14) . . . . ? _diffrn_measured_fraction_theta_max 0.991 _diffrn_reflns_theta_full 27.48 _diffrn_measured_fraction_theta_full 0.991 _refine_diff_density_max 0.250 _refine_diff_density_min -0.287 _refine_diff_density_rms 0.052 data_sw0101 _database_code_CSD 207754 _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C23 H25 N3 O5 S' _chemical_formula_weight 455.52 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 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 12.2145(5) _cell_length_b 7.8483(2) _cell_length_c 23.4165(11) _cell_angle_alpha 90.00 _cell_angle_beta 102.054(2) _cell_angle_gamma 90.00 _cell_volume 2195.28(15) _cell_formula_units_Z 4 _cell_measurement_temperature 180(2) _cell_measurement_reflns_used 8375 _cell_measurement_theta_min 1.0 _cell_measurement_theta_max 25.03 _exptl_crystal_description ? _exptl_crystal_colour colourless _exptl_crystal_size_max 0.41 _exptl_crystal_size_mid 0.23 _exptl_crystal_size_min 0.09 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.378 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 960 _exptl_absorpt_coefficient_mu 0.188 _exptl_absorpt_correction_type multiscan _exptl_absorpt_correction_T_max 1.000 _exptl_absorpt_correction_T_min 0.959 _exptl_absorpt_process_details ; Sortav Blessing (1995) multi-scan from symmetry-related measurements (Blessing 1995) ; _exptl_special_details ; ? ; _diffrn_ambient_temperature 180(2) _diffrn_radiation_wavelength 0.71069 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_measurement_device_type KappaCCD _diffrn_measurement_device '95mm CCD camera on \k-goniostat' _diffrn_detector_area_resol_mean 9 _diffrn_radiation_monochromator 'horizonally mounted graphite crystal' _diffrn_measurement_method CCD _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 11499 _diffrn_reflns_av_R_equivalents 0.0404 _diffrn_reflns_av_sigmaI/netI 0.0461 _diffrn_reflns_limit_h_min -14 _diffrn_reflns_limit_h_max 14 _diffrn_reflns_limit_k_min -8 _diffrn_reflns_limit_k_max 8 _diffrn_reflns_limit_l_min -21 _diffrn_reflns_limit_l_max 27 _diffrn_reflns_theta_min 3.56 _diffrn_reflns_theta_max 25.03 _reflns_number_total 3763 _reflns_number_gt 2903 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Collect (Nonius BV, 1997-2000)' _computing_cell_refinement 'HKL Scalepack (Otwinowski & Minor 1997)' _computing_data_reduction ; HKL Denzo and Scalepack (Otwinowski & Minor 1997) ; _computing_structure_solution teXsan _computing_structure_refinement 'SHELXL-93 (Sheldrick, 1993)' _computing_molecular_graphics ? _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^)+(0.0454P)^2^+0.7826P] 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 3763 _refine_ls_number_parameters 290 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0575 _refine_ls_R_factor_gt 0.0389 _refine_ls_wR_factor_ref 0.1035 _refine_ls_wR_factor_gt 0.0904 _refine_ls_goodness_of_fit_ref 1.040 _refine_ls_restrained_S_all 1.040 _refine_ls_shift/su_max 0.002 _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 0.19412(4) -0.03504(6) 0.29306(2) 0.03417(16) Uani 1 1 d . . . O1 O -0.11976(14) 0.4683(2) -0.07699(7) 0.0556(5) Uani 1 1 d . . . O2 O -0.29791(14) 0.4410(2) -0.08256(6) 0.0503(4) Uani 1 1 d . . . O3 O -0.31543(13) 0.0037(2) 0.13417(7) 0.0533(4) Uani 1 1 d . . . O4 O -0.43317(13) 0.1120(3) 0.06102(8) 0.0639(5) Uani 1 1 d . . . O5 O 0.12887(11) 0.07112(18) 0.05960(6) 0.0375(4) Uani 1 1 d . . . N1 N 0.11257(12) 0.13736(19) 0.15254(6) 0.0250(4) Uani 1 1 d . . . N2 N -0.20057(17) 0.4127(2) -0.05944(7) 0.0387(4) Uani 1 1 d . . . C1 C 0.22744(14) 0.0792(2) 0.18310(8) 0.0241(4) Uani 1 1 d . . . C2 C 0.23018(15) 0.1378(2) 0.24693(8) 0.0257(4) Uani 1 1 d . . . H2 H 0.3064 0.1826 0.2646 0.031 Uiso 1 1 calc R . . N3 N -0.33809(15) 0.0832(2) 0.08820(8) 0.0416(5) Uani 1 1 d . . . C3 C 0.14423(16) 0.2826(2) 0.24233(8) 0.0301(4) Uani 1 1 d . . . H3 H 0.1154 0.2875 0.2792 0.036 Uiso 1 1 calc R . . C4 C 0.05179(16) 0.2200(3) 0.19322(8) 0.0329(5) Uani 1 1 d . . . H4A H 0.0027 0.1376 0.2078 0.039 Uiso 1 1 calc R . . H4B H 0.0057 0.3161 0.1741 0.039 Uiso 1 1 calc R . . C5 C 0.23742(15) -0.1127(2) 0.17410(8) 0.0283(4) Uani 1 1 d . . . H5A H 0.1826 -0.1724 0.1928 0.034 Uiso 1 1 calc R . . H5B H 0.2179 -0.1378 0.1318 0.034 Uiso 1 1 calc R . . C6 C 0.35424(16) -0.1828(3) 0.19918(9) 0.0357(5) Uani 1 1 d . . . H6A H 0.3714 -0.1692 0.2422 0.043 Uiso 1 1 calc R . . H6B H 0.3564 -0.3060 0.1903 0.043 Uiso 1 1 calc R . . C7 C 0.44182(17) -0.0895(3) 0.17340(10) 0.0404(5) Uani 1 1 d . . . H7A H 0.5173 -0.1328 0.1914 0.048 Uiso 1 1 calc R . . H7B H 0.4285 -0.1111 0.1309 0.048 Uiso 1 1 calc R . . C8 C 0.43627(16) 0.1005(3) 0.18444(9) 0.0364(5) Uani 1 1 d . . . H8A H 0.4923 0.1599 0.1666 0.044 Uiso 1 1 calc R . . H8B H 0.4552 0.1222 0.2270 0.044 Uiso 1 1 calc R . . C9 C 0.32002(15) 0.1719(2) 0.15908(8) 0.0291(4) Uani 1 1 d . . . H9A H 0.3044 0.1606 0.1160 0.035 Uiso 1 1 calc R . . H9B H 0.3186 0.2947 0.1686 0.035 Uiso 1 1 calc R . . C10 C 0.1867(2) 0.4585(3) 0.22982(9) 0.0412(5) Uani 1 1 d . . . H10A H 0.1311 0.5447 0.2343 0.062 Uiso 1 1 calc R . . H10B H 0.1991 0.4617 0.1898 0.062 Uiso 1 1 calc R . . H10C H 0.2573 0.4822 0.2573 0.062 Uiso 1 1 calc R . . C11 C 0.24409(17) 0.0579(2) 0.36283(8) 0.0317(5) Uani 1 1 d . . . C12 C 0.17147(19) 0.1290(3) 0.39457(9) 0.0395(5) Uani 1 1 d . . . H12 H 0.0932 0.1299 0.3789 0.047 Uiso 1 1 calc R . . C13 C 0.2140(2) 0.1996(3) 0.44976(10) 0.0540(7) Uani 1 1 d . . . H13 H 0.1643 0.2485 0.4715 0.065 Uiso 1 1 calc R . . C14 C 0.3268(3) 0.1985(4) 0.47252(11) 0.0661(8) Uani 1 1 d . . . H14 H 0.3554 0.2469 0.5098 0.079 Uiso 1 1 calc R . . C15 C 0.3981(2) 0.1272(4) 0.44128(12) 0.0661(8) Uani 1 1 d . . . H15 H 0.4763 0.1262 0.4573 0.079 Uiso 1 1 calc R . . C16 C 0.35834(19) 0.0571(3) 0.38701(10) 0.0467(6) Uani 1 1 d . . . H16 H 0.4091 0.0079 0.3660 0.056 Uiso 1 1 calc R . . C17 C 0.07358(15) 0.1233(2) 0.09436(8) 0.0277(4) Uani 1 1 d . . . C18 C -0.04689(15) 0.1716(2) 0.07008(8) 0.0270(4) Uani 1 1 d . . . C19 C -0.06895(16) 0.2691(2) 0.01935(8) 0.0297(4) Uani 1 1 d . . . H19 H -0.0092 0.3103 0.0029 0.036 Uiso 1 1 calc R . . C20 C -0.17806(16) 0.3054(2) -0.00670(8) 0.0306(5) Uani 1 1 d . . . C21 C -0.26806(16) 0.2452(2) 0.01399(9) 0.0325(5) Uani 1 1 d . . . H21 H -0.3429 0.2692 -0.0053 0.039 Uiso 1 1 calc R . . C22 C -0.24423(16) 0.1485(2) 0.06388(8) 0.0309(5) Uani 1 1 d . . . C23 C -0.13574(16) 0.1113(2) 0.09257(8) 0.0303(5) Uani 1 1 d . . . H23 H -0.1225 0.0452 0.1273 0.036 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 0.0451(3) 0.0298(3) 0.0284(3) 0.0041(2) 0.0095(2) -0.0089(2) O1 0.0628(11) 0.0593(11) 0.0394(10) 0.0159(8) -0.0011(8) -0.0185(9) O2 0.0546(10) 0.0511(10) 0.0365(9) 0.0064(7) -0.0109(8) 0.0119(8) O3 0.0433(9) 0.0785(12) 0.0399(10) 0.0115(9) 0.0126(8) -0.0041(8) O4 0.0270(9) 0.0978(14) 0.0637(12) 0.0150(10) 0.0022(8) 0.0001(9) O5 0.0358(8) 0.0508(9) 0.0261(8) -0.0046(6) 0.0071(6) 0.0088(7) N1 0.0244(8) 0.0271(8) 0.0232(8) -0.0018(6) 0.0046(7) 0.0030(6) N2 0.0521(12) 0.0314(10) 0.0270(10) -0.0005(7) -0.0049(9) -0.0009(9) C1 0.0233(10) 0.0253(10) 0.0230(10) 0.0016(7) 0.0034(8) -0.0008(8) C2 0.0289(10) 0.0239(10) 0.0243(10) 0.0022(8) 0.0054(8) -0.0051(8) N3 0.0323(11) 0.0534(12) 0.0392(11) -0.0025(9) 0.0075(9) -0.0007(8) C3 0.0400(11) 0.0284(11) 0.0230(10) -0.0023(8) 0.0095(9) 0.0016(9) C4 0.0323(11) 0.0384(12) 0.0295(11) -0.0036(9) 0.0097(9) 0.0087(9) C5 0.0301(11) 0.0256(11) 0.0291(11) -0.0017(8) 0.0057(9) -0.0010(8) C6 0.0335(11) 0.0303(11) 0.0424(13) 0.0027(9) 0.0060(9) 0.0064(9) C7 0.0276(11) 0.0449(13) 0.0492(14) 0.0029(10) 0.0090(10) 0.0087(9) C8 0.0263(11) 0.0450(13) 0.0393(12) -0.0013(10) 0.0099(9) -0.0056(9) C9 0.0319(11) 0.0272(10) 0.0296(11) 0.0002(8) 0.0096(9) -0.0039(8) C10 0.0670(15) 0.0270(11) 0.0315(12) -0.0008(9) 0.0146(11) 0.0027(10) C11 0.0374(12) 0.0303(11) 0.0275(11) 0.0088(8) 0.0074(9) -0.0054(9) C12 0.0495(13) 0.0357(12) 0.0359(13) 0.0069(9) 0.0152(11) -0.0054(10) C13 0.092(2) 0.0406(14) 0.0383(14) 0.0026(11) 0.0331(14) -0.0120(13) C14 0.097(2) 0.0670(18) 0.0295(14) 0.0047(12) 0.0015(15) -0.0381(17) C15 0.0584(17) 0.085(2) 0.0450(16) 0.0189(15) -0.0128(14) -0.0281(15) C16 0.0413(13) 0.0563(15) 0.0411(14) 0.0141(11) 0.0054(11) -0.0046(11) C17 0.0290(11) 0.0264(10) 0.0272(11) -0.0005(8) 0.0045(9) 0.0008(8) C18 0.0307(11) 0.0251(10) 0.0242(10) -0.0028(8) 0.0033(8) 0.0022(8) C19 0.0337(11) 0.0282(10) 0.0265(11) -0.0048(8) 0.0046(9) -0.0025(9) C20 0.0397(12) 0.0251(10) 0.0241(11) -0.0020(8) 0.0000(9) 0.0016(9) C21 0.0310(11) 0.0320(11) 0.0308(11) -0.0040(9) -0.0020(9) 0.0047(9) C22 0.0299(11) 0.0321(11) 0.0307(11) -0.0024(8) 0.0062(9) 0.0004(9) C23 0.0333(11) 0.0307(11) 0.0259(11) 0.0016(8) 0.0037(9) 0.0017(9) _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 C11 1.777(2) . ? S1 C2 1.8436(18) . ? O1 N2 1.226(2) . ? O2 N2 1.219(2) . ? O3 N3 1.225(2) . ? O4 N3 1.223(2) . ? O5 C17 1.231(2) . ? N1 C17 1.351(2) . ? N1 C4 1.475(2) . ? N1 C1 1.507(2) . ? N2 C20 1.473(2) . ? C1 C5 1.530(3) . ? C1 C9 1.546(2) . ? C1 C2 1.557(2) . ? C2 C3 1.536(3) . ? C2 H2 1.0000 . ? N3 C22 1.474(3) . ? C3 C4 1.515(3) . ? C3 C10 1.524(3) . ? C3 H3 1.0000 . ? C4 H4A 0.9900 . ? C4 H4B 0.9900 . ? C5 C6 1.528(3) . ? C5 H5A 0.9900 . ? C5 H5B 0.9900 . ? C6 C7 1.522(3) . ? C6 H6A 0.9900 . ? C6 H6B 0.9900 . ? C7 C8 1.517(3) . ? C7 H7A 0.9900 . ? C7 H7B 0.9900 . ? C8 C9 1.527(3) . ? C8 H8A 0.9900 . ? C8 H8B 0.9900 . ? C9 H9A 0.9900 . ? C9 H9B 0.9900 . ? C10 H10A 0.9800 . ? C10 H10B 0.9800 . ? C10 H10C 0.9800 . ? C11 C12 1.388(3) . ? C11 C16 1.392(3) . ? C12 C13 1.402(3) . ? C12 H12 0.9500 . ? C13 C14 1.370(4) . ? C13 H13 0.9500 . ? C14 C15 1.369(4) . ? C14 H14 0.9500 . ? C15 C16 1.377(3) . ? C15 H15 0.9500 . ? C16 H16 0.9500 . ? C17 C18 1.511(3) . ? C18 C23 1.385(3) . ? C18 C19 1.391(3) . ? C19 C20 1.375(3) . ? C19 H19 0.9500 . ? C20 C21 1.374(3) . ? C21 C22 1.372(3) . ? C21 H21 0.9500 . ? C22 C23 1.386(3) . ? C23 H23 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 C11 S1 C2 99.11(8) . . ? C17 N1 C4 124.65(15) . . ? C17 N1 C1 123.48(14) . . ? C4 N1 C1 111.77(14) . . ? O2 N2 O1 124.42(18) . . ? O2 N2 C20 118.04(19) . . ? O1 N2 C20 117.54(17) . . ? N1 C1 C5 109.03(14) . . ? N1 C1 C9 111.35(14) . . ? C5 C1 C9 109.15(15) . . ? N1 C1 C2 101.41(14) . . ? C5 C1 C2 115.88(15) . . ? C9 C1 C2 109.85(14) . . ? C3 C2 C1 105.88(14) . . ? C3 C2 S1 110.01(12) . . ? C1 C2 S1 112.67(12) . . ? C3 C2 H2 109.4 . . ? C1 C2 H2 109.4 . . ? S1 C2 H2 109.4 . . ? O4 N3 O3 124.55(18) . . ? O4 N3 C22 117.72(18) . . ? O3 N3 C22 117.73(17) . . ? C4 C3 C10 112.17(17) . . ? C4 C3 C2 101.73(15) . . ? C10 C3 C2 115.38(16) . . ? C4 C3 H3 109.1 . . ? C10 C3 H3 109.1 . . ? C2 C3 H3 109.1 . . ? N1 C4 C3 103.71(14) . . ? N1 C4 H4A 111.0 . . ? C3 C4 H4A 111.0 . . ? N1 C4 H4B 111.0 . . ? C3 C4 H4B 111.0 . . ? H4A C4 H4B 109.0 . . ? C6 C5 C1 113.37(15) . . ? C6 C5 H5A 108.9 . . ? C1 C5 H5A 108.9 . . ? C6 C5 H5B 108.9 . . ? C1 C5 H5B 108.9 . . ? H5A C5 H5B 107.7 . . ? C7 C6 C5 110.59(16) . . ? C7 C6 H6A 109.5 . . ? C5 C6 H6A 109.5 . . ? C7 C6 H6B 109.5 . . ? C5 C6 H6B 109.5 . . ? H6A C6 H6B 108.1 . . ? C8 C7 C6 110.21(17) . . ? C8 C7 H7A 109.6 . . ? C6 C7 H7A 109.6 . . ? C8 C7 H7B 109.6 . . ? C6 C7 H7B 109.6 . . ? H7A C7 H7B 108.1 . . ? C7 C8 C9 111.45(16) . . ? C7 C8 H8A 109.3 . . ? C9 C8 H8A 109.3 . . ? C7 C8 H8B 109.3 . . ? C9 C8 H8B 109.3 . . ? H8A C8 H8B 108.0 . . ? C8 C9 C1 112.15(16) . . ? C8 C9 H9A 109.2 . . ? C1 C9 H9A 109.2 . . ? C8 C9 H9B 109.2 . . ? C1 C9 H9B 109.2 . . ? H9A C9 H9B 107.9 . . ? C3 C10 H10A 109.5 . . ? C3 C10 H10B 109.5 . . ? H10A C10 H10B 109.5 . . ? C3 C10 H10C 109.5 . . ? H10A C10 H10C 109.5 . . ? H10B C10 H10C 109.5 . . ? C12 C11 C16 118.9(2) . . ? C12 C11 S1 121.48(16) . . ? C16 C11 S1 119.65(17) . . ? C11 C12 C13 119.8(2) . . ? C11 C12 H12 120.1 . . ? C13 C12 H12 120.1 . . ? C14 C13 C12 120.3(2) . . ? C14 C13 H13 119.9 . . ? C12 C13 H13 119.9 . . ? C15 C14 C13 119.7(2) . . ? C15 C14 H14 120.1 . . ? C13 C14 H14 120.1 . . ? C14 C15 C16 121.0(3) . . ? C14 C15 H15 119.5 . . ? C16 C15 H15 119.5 . . ? C15 C16 C11 120.3(2) . . ? C15 C16 H16 119.9 . . ? C11 C16 H16 119.9 . . ? O5 C17 N1 124.58(17) . . ? O5 C17 C18 117.40(16) . . ? N1 C17 C18 118.00(16) . . ? C23 C18 C19 119.03(17) . . ? C23 C18 C17 123.37(17) . . ? C19 C18 C17 117.33(17) . . ? C20 C19 C18 119.31(18) . . ? C20 C19 H19 120.3 . . ? C18 C19 H19 120.3 . . ? C21 C20 C19 123.05(18) . . ? C21 C20 N2 117.99(18) . . ? C19 C20 N2 118.96(18) . . ? C22 C21 C20 116.55(18) . . ? C22 C21 H21 121.7 . . ? C20 C21 H21 121.7 . . ? C21 C22 C23 122.72(18) . . ? C21 C22 N3 118.50(17) . . ? C23 C22 N3 118.78(18) . . ? C18 C23 C22 119.32(18) . . ? C18 C23 H23 120.3 . . ? C22 C23 H23 120.3 . . ? 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 C17 N1 C1 C5 -61.4(2) . . . . ? C4 N1 C1 C5 122.10(16) . . . . ? C17 N1 C1 C9 59.1(2) . . . . ? C4 N1 C1 C9 -117.42(17) . . . . ? C17 N1 C1 C2 175.91(16) . . . . ? C4 N1 C1 C2 -0.62(18) . . . . ? N1 C1 C2 C3 -23.16(17) . . . . ? C5 C1 C2 C3 -141.04(15) . . . . ? C9 C1 C2 C3 94.72(17) . . . . ? N1 C1 C2 S1 97.12(14) . . . . ? C5 C1 C2 S1 -20.75(19) . . . . ? C9 C1 C2 S1 -144.99(13) . . . . ? C11 S1 C2 C3 -77.86(14) . . . . ? C11 S1 C2 C1 164.25(13) . . . . ? C1 C2 C3 C4 37.92(18) . . . . ? S1 C2 C3 C4 -84.08(15) . . . . ? C1 C2 C3 C10 -83.75(19) . . . . ? S1 C2 C3 C10 154.24(14) . . . . ? C17 N1 C4 C3 -152.23(17) . . . . ? C1 N1 C4 C3 24.3(2) . . . . ? C10 C3 C4 N1 86.63(19) . . . . ? C2 C3 C4 N1 -37.24(18) . . . . ? N1 C1 C5 C6 175.29(15) . . . . ? C9 C1 C5 C6 53.5(2) . . . . ? C2 C1 C5 C6 -71.1(2) . . . . ? C1 C5 C6 C7 -56.3(2) . . . . ? C5 C6 C7 C8 56.8(2) . . . . ? C6 C7 C8 C9 -57.5(2) . . . . ? C7 C8 C9 C1 56.5(2) . . . . ? N1 C1 C9 C8 -173.44(15) . . . . ? C5 C1 C9 C8 -53.0(2) . . . . ? C2 C1 C9 C8 75.04(19) . . . . ? C2 S1 C11 C12 103.25(17) . . . . ? C2 S1 C11 C16 -78.00(17) . . . . ? C16 C11 C12 C13 0.6(3) . . . . ? S1 C11 C12 C13 179.33(15) . . . . ? C11 C12 C13 C14 -0.1(3) . . . . ? C12 C13 C14 C15 -0.3(4) . . . . ? C13 C14 C15 C16 0.3(4) . . . . ? C14 C15 C16 C11 0.2(4) . . . . ? C12 C11 C16 C15 -0.6(3) . . . . ? S1 C11 C16 C15 -179.39(18) . . . . ? C4 N1 C17 O5 171.75(18) . . . . ? C1 N1 C17 O5 -4.3(3) . . . . ? C4 N1 C17 C18 -9.5(3) . . . . ? C1 N1 C17 C18 174.46(15) . . . . ? O5 C17 C18 C23 129.0(2) . . . . ? N1 C17 C18 C23 -49.9(3) . . . . ? O5 C17 C18 C19 -45.0(2) . . . . ? N1 C17 C18 C19 136.12(18) . . . . ? C23 C18 C19 C20 1.0(3) . . . . ? C17 C18 C19 C20 175.19(16) . . . . ? C18 C19 C20 C21 -2.1(3) . . . . ? C18 C19 C20 N2 178.28(16) . . . . ? O2 N2 C20 C21 -1.0(3) . . . . ? O1 N2 C20 C21 178.75(18) . . . . ? O2 N2 C20 C19 178.70(17) . . . . ? O1 N2 C20 C19 -1.6(3) . . . . ? C19 C20 C21 C22 1.7(3) . . . . ? N2 C20 C21 C22 -178.67(16) . . . . ? C20 C21 C22 C23 -0.2(3) . . . . ? C20 C21 C22 N3 179.13(17) . . . . ? O4 N3 C22 C21 3.3(3) . . . . ? O3 N3 C22 C21 -176.74(19) . . . . ? O4 N3 C22 C23 -177.29(19) . . . . ? O3 N3 C22 C23 2.6(3) . . . . ? C19 C18 C23 C22 0.4(3) . . . . ? C17 C18 C23 C22 -173.44(17) . . . . ? C21 C22 C23 C18 -0.8(3) . . . . ? N3 C22 C23 C18 179.85(17) . . . . ? _diffrn_measured_fraction_theta_max 0.968 _diffrn_reflns_theta_full 25.03 _diffrn_measured_fraction_theta_full 0.968 _refine_diff_density_max 0.202 _refine_diff_density_min -0.243 _refine_diff_density_rms 0.054