# Supplementary Material (ESI) for Perkin Transactions # This journal is © The Royal Society of Chemistry 2001 data_s536rm _database_code_CSD 165006 _publ_contact_author ' Joachim Podlech' _publ_contact_author_email joachim.podlech@po.uni-stuttgart.de loop_ _publ_author_name 'Michael R. Linder' 'Wolfgang U. Frey' 'Joachim Podlech' _journal_name_full 'Journal of the Chemical Society, Perkin Transactions 1' _journal_coden_Cambridge 207 _audit_creation_method SHELXL _chemical_name_systematic ; (3S,4R,1'S)-1-Benzyl-3-[1-(benzyloxycarbonylamino)ethyl]-4- (4-methoxyphenyl)-azetidin-2-one # The configuration has been determined relative to the configuration at 1' # which is given by the synthetic precursors ; _chemical_name_common ? _chemical_formula_moiety ? _chemical_formula_structural ? _chemical_formula_analytical ? _chemical_formula_sum 'C27 H28 N2 O4' _chemical_formula_weight 444.51 _chemical_melting_point '375 - 376 K' _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' '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' _symmetry_cell_setting orthorhombic _symmetry_space_group_name_H-M p2(1)2(1)2(1) 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 9.5340(10) _cell_length_b 9.689(2) _cell_length_c 26.056(4) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 2406.9(7) _cell_formula_units_Z 4 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 26 _cell_measurement_theta_min 10 _cell_measurement_theta_max 13 _exptl_crystal_description block _exptl_crystal_colour colourless _exptl_crystal_size_max 0.4 _exptl_crystal_size_mid 0.4 _exptl_crystal_size_min 0.2 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.227 _exptl_crystal_density_method ? _exptl_crystal_F_000 944 _exptl_absorpt_coefficient_mu 0.083 _exptl_absorpt_correction_type none _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 293(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device Nicolet P3 _diffrn_measurement_method Wyckoff - Scan _diffrn_standards_number 3 _diffrn_standards_interval_count 50 _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 2438 _diffrn_reflns_av_R_equivalents 0.0000 _diffrn_reflns_av_sigmaI/netI 0.0757 _diffrn_reflns_limit_h_min 0 _diffrn_reflns_limit_h_max 11 _diffrn_reflns_limit_k_min 0 _diffrn_reflns_limit_k_max 11 _diffrn_reflns_limit_l_min 0 _diffrn_reflns_limit_l_max 32 _diffrn_reflns_theta_min 1.56 _diffrn_reflns_theta_max 25.00 _reflns_number_total 2438 _reflns_number_observed 1352 _reflns_observed_criterion >2sigma(I) _computing_data_collection Siemens P3/V Data Collection System _computing_cell_refinement Siemens P3/V Data Collection System _computing_data_reduction SHELXTL plus - XDISK _computing_structure_solution 'SHELXS-86 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-93 (Sheldrick, 1993)' _computing_molecular_graphics SHELXTL - XP _computing_publication_material ? _refine_special_details ; Refinement on F^2^ for ALL reflections except for 348 with very negative F^2^ or flagged by the user for potential systematic errors. Weighted R-factors wR and all goodnesses 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 observed criterion of F^2^ > 2sigma(F^2^) is used only for calculating _R_factor_obs 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 w=1/[\s^2^(Fo^2^)+(0.0340P)^2^+0.0122P] 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 ? _refine_ls_extinction_method SHELXL _refine_ls_extinction_coef 0.0370(18) _refine_ls_extinction_expression 'Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^' _refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _refine_ls_abs_structure_Flack -1.49(249) _refine_ls_number_reflns 2090 _refine_ls_number_parameters 299 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.1281 _refine_ls_R_factor_obs 0.0552 _refine_ls_wR_factor_all 0.1111 _refine_ls_wR_factor_obs 0.0847 _refine_ls_goodness_of_fit_all 1.092 _refine_ls_goodness_of_fit_obs 1.261 _refine_ls_restrained_S_all 1.164 _refine_ls_restrained_S_obs 1.261 _refine_ls_shift/esd_max 0.000 _refine_ls_shift/esd_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_thermal_displace_type _atom_site_occupancy _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_group N1 N 0.4285(4) 0.5990(4) 0.9186(2) 0.0628(11) Uani 1 d . . O1 O 0.4354(4) 0.7334(3) 0.99304(14) 0.0757(11) Uani 1 d . . C1 C 0.4751(5) 0.6432(5) 0.9646(2) 0.0574(13) Uani 1 d . . O2 O 0.4963(3) 0.1746(3) 0.97460(10) 0.0547(9) Uani 1 d . . N2 N 0.6774(4) 0.3131(4) 0.99840(13) 0.0496(10) Uani 1 d . . H2 H 0.7667(4) 0.3171(4) 1.00263(13) 0.060 Uiso 1 calc R . C2 C 0.5909(5) 0.5334(4) 0.9648(2) 0.0489(12) Uani 1 d . . H2A H 0.6835(5) 0.5746(4) 0.9591(2) 0.059 Uiso 1 calc R . O3 O 0.7211(3) 0.1001(3) 0.97204(11) 0.0578(9) Uani 1 d . . C3 C 0.5245(5) 0.4814(5) 0.9132(2) 0.0559(13) Uani 1 d . . H3 H 0.4750(5) 0.3938(5) 0.9182(2) 0.067 Uiso 1 calc R . C4 C 0.5925(5) 0.4348(4) 1.0099(2) 0.0471(12) Uani 1 d . . H4 H 0.4961(5) 0.4047(4) 1.0166(2) 0.057 Uiso 1 calc R . O4 O 0.8636(4) 0.4712(5) 0.73498(13) 0.0933(12) Uani 1 d . . C5 C 0.6480(5) 0.5069(5) 1.0578(2) 0.0682(15) Uani 1 d . . H5A H 0.6483(5) 0.4432(5) 1.0860(2) 0.102 Uiso 1 calc R . H5B H 0.5888(5) 0.5840(5) 1.0659(2) 0.102 Uiso 1 calc R . H5C H 0.7417(5) 0.5389(5) 1.0515(2) 0.102 Uiso 1 calc R . C6 C 0.6201(5) 0.1958(5) 0.9815(2) 0.0504(12) Uani 1 d . . C7 C 0.6716(5) -0.0313(5) 0.9519(2) 0.0624(14) Uani 1 d . . H7A H 0.5849(5) -0.0565(5) 0.9689(2) 0.075 Uiso 1 calc R . H7B H 0.7405(5) -0.1024(5) 0.9592(2) 0.075 Uiso 1 calc R . C8 C 0.6473(5) -0.0250(5) 0.8952(2) 0.0557(13) Uani 1 d . . C9 C 0.7577(6) -0.0252(6) 0.8610(2) 0.076(2) Uani 1 d . . H9 H 0.8496(6) -0.0283(6) 0.8729(2) 0.091 Uiso 1 calc R . C10 C 0.7309(8) -0.0206(6) 0.8078(3) 0.093(2) Uani 1 d . . H10 H 0.8047(8) -0.0202(6) 0.7844(3) 0.111 Uiso 1 calc R . C11 C 0.5967(9) -0.0167(6) 0.7912(2) 0.097(2) Uani 1 d . . H11 H 0.5795(9) -0.0160(6) 0.7560(2) 0.117 Uiso 1 calc R . C12 C 0.4862(7) -0.0138(7) 0.8240(2) 0.098(2) Uani 1 d . . H12 H 0.3947(7) -0.0083(7) 0.8118(2) 0.118 Uiso 1 calc R . C13 C 0.5139(5) -0.0194(6) 0.8761(2) 0.075(2) Uani 1 d . . H13 H 0.4389(5) -0.0193(6) 0.8989(2) 0.089 Uiso 1 calc R . C14 C 0.3117(6) 0.6399(5) 0.8859(2) 0.086(2) Uani 1 d . . H14A H 0.3477(6) 0.6653(5) 0.8524(2) 0.103 Uiso 1 calc R . H14B H 0.2670(6) 0.7207(5) 0.9006(2) 0.103 Uiso 1 calc R . C15 C 0.2041(5) 0.5283(6) 0.8795(2) 0.0584(13) Uani 1 d . . C16 C 0.2281(6) 0.4206(7) 0.8465(2) 0.080(2) Uani 1 d . . H16 H 0.3091(6) 0.4200(7) 0.8266(2) 0.096 Uiso 1 calc R . C17 C 0.1342(9) 0.3133(8) 0.8425(3) 0.111(2) Uani 1 d . . H17 H 0.1526(9) 0.2396(8) 0.8206(3) 0.133 Uiso 1 calc R . C18 C 0.0161(10) 0.3162(10) 0.8703(4) 0.130(4) Uani 1 d . . H18 H -0.0474(10) 0.2437(10) 0.8677(4) 0.156 Uiso 1 calc R . C19 C -0.0123(8) 0.4233(11) 0.9021(3) 0.119(3) Uani 1 d . . H19 H -0.0962(8) 0.4256(11) 0.9204(3) 0.142 Uiso 1 calc R . C20 C 0.0833(7) 0.5285(8) 0.9074(2) 0.090(2) Uani 1 d . . H20 H 0.0654(7) 0.6002(8) 0.9302(2) 0.108 Uiso 1 calc R . C21 C 0.6104(5) 0.4784(5) 0.8655(2) 0.0530(12) Uani 1 d . . C22 C 0.6734(6) 0.5965(5) 0.8455(2) 0.076(2) Uani 1 d . . H22 H 0.6593(6) 0.6809(5) 0.8617(2) 0.091 Uiso 1 calc R . C23 C 0.7562(6) 0.5907(6) 0.8022(2) 0.081(2) Uani 1 d . . H23 H 0.7975(6) 0.6708(6) 0.7896(2) 0.097 Uiso 1 calc R . C24 C 0.7781(5) 0.4667(6) 0.7773(2) 0.0647(14) Uani 1 d . . C25 C 0.7164(6) 0.3496(5) 0.7962(2) 0.067(2) Uani 1 d . . H25 H 0.7304(6) 0.2654(5) 0.7798(2) 0.081 Uiso 1 calc R . C26 C 0.6329(5) 0.3564(5) 0.8399(2) 0.0595(15) Uani 1 d . . H26 H 0.5911(5) 0.2761(5) 0.8520(2) 0.071 Uiso 1 calc R . C27 C 0.8961(7) 0.3439(7) 0.7111(2) 0.113(2) Uani 1 d . . H27A H 0.9561(7) 0.3601(7) 0.6821(2) 0.170 Uiso 1 calc R . H27B H 0.8111(7) 0.3003(7) 0.6997(2) 0.170 Uiso 1 calc R . H27C H 0.9430(7) 0.2848(7) 0.7351(2) 0.170 Uiso 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 N1 0.055(3) 0.054(2) 0.080(3) -0.002(2) -0.016(2) 0.015(2) O1 0.084(3) 0.047(2) 0.097(3) -0.016(2) 0.008(2) -0.001(2) C1 0.062(3) 0.043(3) 0.067(3) -0.003(3) -0.001(3) -0.011(3) O2 0.044(2) 0.050(2) 0.070(2) -0.011(2) -0.005(2) -0.008(2) N2 0.039(2) 0.041(2) 0.068(3) -0.009(2) -0.007(2) -0.008(2) C2 0.045(3) 0.042(3) 0.060(3) -0.002(3) 0.001(3) -0.008(3) O3 0.048(2) 0.049(2) 0.077(2) -0.009(2) -0.013(2) 0.010(2) C3 0.062(3) 0.037(3) 0.069(3) 0.002(3) -0.007(3) -0.004(3) C4 0.047(3) 0.038(3) 0.056(3) -0.007(2) 0.000(3) -0.006(2) O4 0.103(3) 0.117(3) 0.060(2) 0.000(3) 0.017(2) -0.016(3) C5 0.073(3) 0.068(4) 0.063(3) -0.018(3) -0.009(3) -0.009(3) C6 0.042(3) 0.056(3) 0.054(3) 0.007(3) -0.005(3) -0.006(3) C7 0.067(3) 0.039(3) 0.081(4) -0.003(3) -0.005(3) -0.001(3) C8 0.056(3) 0.038(3) 0.074(4) -0.007(3) 0.000(3) -0.003(3) C9 0.061(4) 0.063(4) 0.104(5) -0.004(4) 0.013(4) 0.003(3) C10 0.110(6) 0.071(4) 0.098(5) -0.010(4) 0.045(5) -0.009(4) C11 0.129(6) 0.086(5) 0.077(4) -0.022(4) 0.008(5) -0.016(6) C12 0.090(5) 0.122(5) 0.082(4) -0.012(5) -0.008(4) -0.023(5) C13 0.062(4) 0.084(4) 0.077(4) -0.014(4) 0.006(3) -0.019(4) C14 0.076(4) 0.064(4) 0.116(5) 0.010(4) -0.027(4) 0.002(4) C15 0.044(3) 0.072(4) 0.059(3) 0.005(3) -0.010(3) 0.006(3) C16 0.079(4) 0.092(4) 0.070(4) -0.012(4) 0.002(3) 0.006(4) C17 0.124(6) 0.089(5) 0.119(6) -0.017(5) -0.057(5) -0.007(6) C18 0.086(6) 0.115(7) 0.189(10) 0.059(7) -0.069(7) -0.022(7) C19 0.058(4) 0.176(9) 0.122(7) 0.063(6) -0.006(5) 0.000(7) C20 0.063(4) 0.133(6) 0.073(4) 0.005(4) -0.011(4) 0.020(5) C21 0.063(3) 0.045(3) 0.051(3) 0.004(3) -0.003(3) -0.002(3) C22 0.098(4) 0.050(3) 0.081(4) 0.002(3) 0.016(4) -0.014(3) C23 0.104(5) 0.060(4) 0.078(4) 0.011(4) 0.007(4) -0.022(4) C24 0.072(4) 0.072(4) 0.050(3) 0.004(3) -0.009(3) -0.008(4) C25 0.081(4) 0.058(4) 0.063(4) -0.004(3) -0.001(3) 0.001(3) C26 0.071(4) 0.046(3) 0.061(3) 0.003(3) -0.004(3) -0.006(3) C27 0.103(5) 0.150(6) 0.087(4) -0.031(5) 0.030(4) -0.020(5) _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 N1 C1 1.347(6) . ? N1 C14 1.457(6) . ? N1 C3 1.468(6) . ? O1 C1 1.207(5) . ? C1 C2 1.534(6) . ? O2 C6 1.211(5) . ? N2 C6 1.336(5) . ? N2 C4 1.461(5) . ? N2 H2 0.86 . ? C2 C4 1.515(5) . ? C2 C3 1.568(5) . ? C2 H2A 0.98 . ? O3 C6 1.359(5) . ? O3 C7 1.456(5) . ? C3 C21 1.488(6) . ? C3 H3 0.98 . ? C4 C5 1.523(5) . ? C4 H4 0.98 . ? O4 C24 1.372(6) . ? O4 C27 1.417(6) . ? C5 H5A 0.96 . ? C5 H5B 0.96 . ? C5 H5C 0.96 . ? C7 C8 1.496(6) . ? C7 H7A 0.97 . ? C7 H7B 0.97 . ? C8 C13 1.367(6) . ? C8 C9 1.380(6) . ? C9 C10 1.411(7) . ? C9 H9 0.93 . ? C10 C11 1.351(8) . ? C10 H10 0.93 . ? C11 C12 1.357(8) . ? C11 H11 0.93 . ? C12 C13 1.384(7) . ? C12 H12 0.93 . ? C13 H13 0.93 . ? C14 C15 1.501(6) . ? C14 H14A 0.97 . ? C14 H14B 0.97 . ? C15 C20 1.362(7) . ? C15 C16 1.371(6) . ? C16 C17 1.376(8) . ? C16 H16 0.93 . ? C17 C18 1.340(10) . ? C17 H17 0.93 . ? C18 C19 1.357(11) . ? C18 H18 0.93 . ? C19 C20 1.374(9) . ? C19 H19 0.93 . ? C20 H20 0.93 . ? C21 C26 1.375(6) . ? C21 C22 1.393(6) . ? C22 C23 1.380(7) . ? C22 H22 0.93 . ? C23 C24 1.380(6) . ? C23 H23 0.93 . ? C24 C25 1.370(6) . ? C25 C26 1.390(6) . ? C25 H25 0.93 . ? C26 H26 0.93 . ? C27 H27A 0.96 . ? C27 H27B 0.96 . ? C27 H27C 0.96 . ? 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 C1 N1 C14 133.2(4) . . ? C1 N1 C3 97.3(4) . . ? C14 N1 C3 129.2(4) . . ? O1 C1 N1 132.3(5) . . ? O1 C1 C2 136.5(5) . . ? N1 C1 C2 91.1(4) . . ? C6 N2 C4 121.9(4) . . ? C6 N2 H2 119.1(3) . . ? C4 N2 H2 119.1(2) . . ? C4 C2 C1 116.6(4) . . ? C4 C2 C3 117.8(3) . . ? C1 C2 C3 85.9(3) . . ? C4 C2 H2A 111.4(2) . . ? C1 C2 H2A 111.4(2) . . ? C3 C2 H2A 111.4(2) . . ? C6 O3 C7 115.6(4) . . ? N1 C3 C21 116.0(4) . . ? N1 C3 C2 85.5(3) . . ? C21 C3 C2 120.0(4) . . ? N1 C3 H3 111.0(2) . . ? C21 C3 H3 111.0(3) . . ? C2 C3 H3 111.0(2) . . ? N2 C4 C2 110.8(4) . . ? N2 C4 C5 110.3(4) . . ? C2 C4 C5 110.4(3) . . ? N2 C4 H4 108.4(2) . . ? C2 C4 H4 108.4(2) . . ? C5 C4 H4 108.4(2) . . ? C24 O4 C27 117.1(5) . . ? C4 C5 H5A 109.5(2) . . ? C4 C5 H5B 109.5(2) . . ? H5A C5 H5B 109.5 . . ? C4 C5 H5C 109.5(2) . . ? H5A C5 H5C 109.5 . . ? H5B C5 H5C 109.5 . . ? O2 C6 N2 126.2(5) . . ? O2 C6 O3 123.3(5) . . ? N2 C6 O3 110.5(4) . . ? O3 C7 C8 111.8(4) . . ? O3 C7 H7A 109.3(2) . . ? C8 C7 H7A 109.3(3) . . ? O3 C7 H7B 109.3(2) . . ? C8 C7 H7B 109.3(3) . . ? H7A C7 H7B 107.9 . . ? C13 C8 C9 118.3(5) . . ? C13 C8 C7 120.4(5) . . ? C9 C8 C7 121.3(5) . . ? C8 C9 C10 119.8(5) . . ? C8 C9 H9 120.1(3) . . ? C10 C9 H9 120.1(4) . . ? C11 C10 C9 119.1(6) . . ? C11 C10 H10 120.4(4) . . ? C9 C10 H10 120.4(4) . . ? C10 C11 C12 122.3(6) . . ? C10 C11 H11 118.8(4) . . ? C12 C11 H11 118.8(4) . . ? C11 C12 C13 118.0(6) . . ? C11 C12 H12 121.0(4) . . ? C13 C12 H12 121.0(4) . . ? C8 C13 C12 122.4(5) . . ? C8 C13 H13 118.8(3) . . ? C12 C13 H13 118.8(4) . . ? N1 C14 C15 113.1(4) . . ? N1 C14 H14A 109.0(3) . . ? C15 C14 H14A 109.0(3) . . ? N1 C14 H14B 109.0(3) . . ? C15 C14 H14B 109.0(3) . . ? H14A C14 H14B 107.8 . . ? C20 C15 C16 118.5(6) . . ? C20 C15 C14 121.2(6) . . ? C16 C15 C14 120.2(5) . . ? C15 C16 C17 121.0(6) . . ? C15 C16 H16 119.5(4) . . ? C17 C16 H16 119.5(5) . . ? C18 C17 C16 119.3(8) . . ? C18 C17 H17 120.3(6) . . ? C16 C17 H17 120.3(5) . . ? C17 C18 C19 121.0(10) . . ? C17 C18 H18 119.5(6) . . ? C19 C18 H18 119.5(6) . . ? C18 C19 C20 119.7(8) . . ? C18 C19 H19 120.1(6) . . ? C20 C19 H19 120.1(5) . . ? C15 C20 C19 120.4(7) . . ? C15 C20 H20 119.8(4) . . ? C19 C20 H20 119.8(5) . . ? C26 C21 C22 117.2(4) . . ? C26 C21 C3 120.6(4) . . ? C22 C21 C3 122.2(4) . . ? C23 C22 C21 121.3(5) . . ? C23 C22 H22 119.4(3) . . ? C21 C22 H22 119.4(3) . . ? C22 C23 C24 120.5(5) . . ? C22 C23 H23 119.8(3) . . ? C24 C23 H23 119.8(3) . . ? C25 C24 O4 124.7(5) . . ? C25 C24 C23 119.2(5) . . ? O4 C24 C23 116.1(5) . . ? C24 C25 C26 120.0(5) . . ? C24 C25 H25 120.0(3) . . ? C26 C25 H25 120.0(3) . . ? C21 C26 C25 121.9(5) . . ? C21 C26 H26 119.0(3) . . ? C25 C26 H26 119.0(3) . . ? O4 C27 H27A 109.5(3) . . ? O4 C27 H27B 109.5(3) . . ? H27A C27 H27B 109.5 . . ? O4 C27 H27C 109.5(3) . . ? H27A C27 H27C 109.5 . . ? H27B C27 H27C 109.5 . . ? 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 C14 N1 C1 O1 -1.5(9) . . . . ? C3 N1 C1 O1 -175.2(5) . . . . ? C14 N1 C1 C2 177.6(5) . . . . ? C3 N1 C1 C2 3.9(3) . . . . ? O1 C1 C2 C4 56.2(7) . . . . ? N1 C1 C2 C4 -122.8(4) . . . . ? O1 C1 C2 C3 175.4(6) . . . . ? N1 C1 C2 C3 -3.6(3) . . . . ? C1 N1 C3 C21 -125.0(4) . . . . ? C14 N1 C3 C21 60.9(6) . . . . ? C1 N1 C3 C2 -3.8(3) . . . . ? C14 N1 C3 C2 -177.9(5) . . . . ? C4 C2 C3 N1 121.3(4) . . . . ? C1 C2 C3 N1 3.3(3) . . . . ? C4 C2 C3 C21 -121.2(4) . . . . ? C1 C2 C3 C21 120.8(4) . . . . ? C6 N2 C4 C2 -96.4(5) . . . . ? C6 N2 C4 C5 141.0(4) . . . . ? C1 C2 C4 N2 162.9(4) . . . . ? C3 C2 C4 N2 62.9(5) . . . . ? C1 C2 C4 C5 -74.7(5) . . . . ? C3 C2 C4 C5 -174.7(4) . . . . ? C4 N2 C6 O2 -1.3(7) . . . . ? C4 N2 C6 O3 178.0(3) . . . . ? C7 O3 C6 O2 1.1(6) . . . . ? C7 O3 C6 N2 -178.2(3) . . . . ? C6 O3 C7 C8 81.8(5) . . . . ? O3 C7 C8 C13 -105.2(6) . . . . ? O3 C7 C8 C9 75.0(6) . . . . ? C13 C8 C9 C10 -0.4(8) . . . . ? C7 C8 C9 C10 179.4(5) . . . . ? C8 C9 C10 C11 -0.3(10) . . . . ? C9 C10 C11 C12 1.6(11) . . . . ? C10 C11 C12 C13 -2.0(10) . . . . ? C9 C8 C13 C12 0.0(9) . . . . ? C7 C8 C13 C12 -179.8(5) . . . . ? C11 C12 C13 C8 1.2(10) . . . . ? C1 N1 C14 C15 -115.2(6) . . . . ? C3 N1 C14 C15 56.8(7) . . . . ? N1 C14 C15 C20 99.6(6) . . . . ? N1 C14 C15 C16 -77.9(6) . . . . ? C20 C15 C16 C17 -1.5(8) . . . . ? C14 C15 C16 C17 176.2(5) . . . . ? C15 C16 C17 C18 1.6(10) . . . . ? C16 C17 C18 C19 0.2(11) . . . . ? C17 C18 C19 C20 -2.2(12) . . . . ? C16 C15 C20 C19 -0.5(8) . . . . ? C14 C15 C20 C19 -178.1(5) . . . . ? C18 C19 C20 C15 2.3(10) . . . . ? N1 C3 C21 C26 -139.4(5) . . . . ? C2 C3 C21 C26 120.2(5) . . . . ? N1 C3 C21 C22 41.9(6) . . . . ? C2 C3 C21 C22 -58.5(6) . . . . ? C26 C21 C22 C23 -0.8(8) . . . . ? C3 C21 C22 C23 177.9(5) . . . . ? C21 C22 C23 C24 0.3(8) . . . . ? C27 O4 C24 C25 -3.7(7) . . . . ? C27 O4 C24 C23 175.4(5) . . . . ? C22 C23 C24 C25 0.1(8) . . . . ? C22 C23 C24 O4 -179.1(5) . . . . ? O4 C24 C25 C26 179.1(4) . . . . ? C23 C24 C25 C26 0.1(7) . . . . ? C22 C21 C26 C25 0.9(7) . . . . ? C3 C21 C26 C25 -177.8(4) . . . . ? C24 C25 C26 C21 -0.6(7) . . . . ? _refine_diff_density_max 0.144 _refine_diff_density_min -0.145 _refine_diff_density_rms 0.033 data_s538rm _database_code_CSD 165007 _publ_contact_author ' Joachim Podlech' _publ_contact_author_email joachim.podlech@po.uni-stuttgart.de loop_ _publ_author_name 'Michael R. Linder' 'Wolfgang U. Frey' 'Joachim Podlech' _journal_name_full 'Journal of the Chemical Society, Perkin Transactions 1' _journal_coden_Cambridge 207 _audit_creation_method SHELXL _chemical_name_systematic ; (3S,4R,1'S)-1-Benzyl-3-[1-(benzyloxycarbonylamino)ethyl]-4- (4-chlorphenyl)-azetidin-2-one # The configuration has been determined relative to the configuration at 1' # which is given by the synthetic precursors ; _chemical_name_common ? _chemical_formula_moiety ? _chemical_formula_structural ? _chemical_formula_analytical ? _chemical_formula_sum 'C26 H25 Cl N2 O3' _chemical_formula_weight 448.93 _chemical_melting_point '398 - 399 K' _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' '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' 'Cl' 'Cl' 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting orthorhombic _symmetry_space_group_name_H-M P2(1)2(1)2(1) 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 9.498(2) _cell_length_b 9.675(2) _cell_length_c 25.765(4) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 2367.6(8) _cell_formula_units_Z 4 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 26 _cell_measurement_theta_min 10 _cell_measurement_theta_max 13 _exptl_crystal_description block _exptl_crystal_colour colourless _exptl_crystal_size_max 0.5 _exptl_crystal_size_mid 0.4 _exptl_crystal_size_min 0.15 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.259 _exptl_crystal_density_method ? _exptl_crystal_F_000 944 _exptl_absorpt_coefficient_mu 0.191 _exptl_absorpt_correction_type none _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 293(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device Nicolet P3 _diffrn_measurement_method Wyckoff - Scan _diffrn_standards_number 3 _diffrn_standards_interval_count 50 _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 3099 _diffrn_reflns_av_R_equivalents 0.0000 _diffrn_reflns_av_sigmaI/netI 0.0745 _diffrn_reflns_limit_h_min 0 _diffrn_reflns_limit_h_max 12 _diffrn_reflns_limit_k_min 0 _diffrn_reflns_limit_k_max 12 _diffrn_reflns_limit_l_min 0 _diffrn_reflns_limit_l_max 33 _diffrn_reflns_theta_min 1.58 _diffrn_reflns_theta_max 27.49 _reflns_number_total 3099 _reflns_number_observed 1413 _reflns_observed_criterion >2sigma(I) _computing_data_collection Siemens P3/V Data Collection System _computing_cell_refinement Siemens P3/V Data Collection System _computing_data_reduction SHELXTL plus - XDISK _computing_structure_solution 'SHELXS-86 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-93 (Sheldrick, 1993)' _computing_molecular_graphics SHELXTL -XP _computing_publication_material ? _refine_special_details ; Refinement on F^2^ for ALL reflections except for 595 with very negative F^2^ or flagged by the user for potential systematic errors. Weighted R-factors wR and all goodnesses 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 observed criterion of F^2^ > 2sigma(F^2^) is used only for calculating _R_factor_obs 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 w=1/[\s^2^(Fo^2^)+(0.0449P)^2^+0.3558P] 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 ? _refine_ls_extinction_method SHELXL _refine_ls_extinction_coef 0.0269(17) _refine_ls_extinction_expression 'Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^' _refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _refine_ls_abs_structure_Flack 0.72(19) _refine_ls_number_reflns 2504 _refine_ls_number_parameters 290 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.1591 _refine_ls_R_factor_obs 0.0598 _refine_ls_wR_factor_all 0.1475 _refine_ls_wR_factor_obs 0.1069 _refine_ls_goodness_of_fit_all 1.036 _refine_ls_goodness_of_fit_obs 1.262 _refine_ls_restrained_S_all 1.107 _refine_ls_restrained_S_obs 1.262 _refine_ls_shift/esd_max -0.006 _refine_ls_shift/esd_mean 0.001 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_thermal_displace_type _atom_site_occupancy _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_group Cl1 Cl 0.1075(2) 0.9201(3) 0.77893(7) 0.1341(9) Uani 1 d . . N1 N 0.5785(4) 1.0977(5) 0.5915(2) 0.0690(12) Uani 1 d . . O1 O 0.5784(4) 1.2334(4) 0.51617(14) 0.0764(11) Uani 1 d . . C1 C 0.5359(5) 1.1432(6) 0.5443(2) 0.0627(14) Uani 1 d . . N2 N 0.3324(4) 0.8174(4) 0.50424(14) 0.0527(10) Uani 1 d . . H2 H 0.2430(4) 0.8223(4) 0.49936(14) 0.063 Uiso 1 calc R . O2 O 0.5131(3) 0.6766(3) 0.52846(12) 0.0600(9) Uani 1 d . . C2 C 0.4196(5) 1.0326(5) 0.5417(2) 0.0511(11) Uani 1 d . . H2A H 0.3267(5) 1.0735(5) 0.5479(2) 0.061 Uiso 1 calc R . O3 O 0.2876(3) 0.6005(4) 0.52705(13) 0.0637(10) Uani 1 d . . C3 C 0.4852(5) 0.9776(5) 0.5933(2) 0.0599(13) Uani 1 d . . H3 H 0.5382(5) 0.8922(5) 0.5871(2) 0.072 Uiso 1 calc R . C4 C 0.4168(4) 0.9389(4) 0.4948(2) 0.0501(12) Uani 1 d . . H4 H 0.5135(4) 0.9091(4) 0.4875(2) 0.060 Uiso 1 calc R . C5 C 0.3622(5) 1.0153(5) 0.4477(2) 0.071(2) Uani 1 d . . H5A H 0.3613(5) 0.9541(5) 0.4184(2) 0.107 Uiso 1 calc R . H5B H 0.4222(5) 1.0927(5) 0.4405(2) 0.107 Uiso 1 calc R . H5C H 0.2683(5) 1.0474(5) 0.4544(2) 0.107 Uiso 1 calc R . C6 C 0.3876(5) 0.6967(5) 0.5204(2) 0.0530(12) Uani 1 d . . C7 C 0.3345(6) 0.4661(5) 0.5449(2) 0.0700(15) Uani 1 d . . H7A H 0.4221(6) 0.4427(5) 0.5276(2) 0.084 Uiso 1 calc R . H7B H 0.2650(6) 0.3971(5) 0.5353(2) 0.084 Uiso 1 calc R . C8 C 0.3563(5) 0.4618(5) 0.6018(2) 0.0625(14) Uani 1 d . . C9 C 0.2451(6) 0.4555(7) 0.6370(3) 0.092(2) Uani 1 d . . H9 H 0.1528(6) 0.4550(7) 0.6250(3) 0.110 Uiso 1 calc R . C10 C 0.2723(9) 0.4499(8) 0.6900(3) 0.106(2) Uani 1 d . . H10 H 0.1982(9) 0.4430(8) 0.7135(3) 0.128 Uiso 1 calc R . C11 C 0.4057(9) 0.4544(8) 0.7073(3) 0.107(2) Uani 1 d . . H11 H 0.4230(9) 0.4536(8) 0.7428(3) 0.128 Uiso 1 calc R . C12 C 0.5125(7) 0.4599(8) 0.6745(2) 0.100(2) Uani 1 d . . H12 H 0.6042(7) 0.4603(8) 0.6871(2) 0.120 Uiso 1 calc R . C13 C 0.4896(6) 0.4651(6) 0.6221(2) 0.075(2) Uani 1 d . . H13 H 0.5662(6) 0.4710(6) 0.5997(2) 0.090 Uiso 1 calc R . C14 C 0.6964(6) 1.1345(6) 0.6249(2) 0.083(2) Uani 1 d . . H14A H 0.6623(6) 1.1473(6) 0.6601(2) 0.100 Uiso 1 calc R . H14B H 0.7358(6) 1.2216(6) 0.6133(2) 0.100 Uiso 1 calc R . C15 C 0.8097(5) 1.0271(6) 0.6250(2) 0.0590(13) Uani 1 d . . C16 C 0.7948(7) 0.9113(8) 0.6551(2) 0.090(2) Uani 1 d . . H16 H 0.7180(7) 0.9034(8) 0.6773(2) 0.108 Uiso 1 calc R . C17 C 0.8911(11) 0.8082(10) 0.6528(4) 0.136(3) Uani 1 d . . H17 H 0.8783(11) 0.7296(10) 0.6731(4) 0.163 Uiso 1 calc R . C18 C 1.0031(12) 0.8169(13) 0.6224(5) 0.158(6) Uani 1 d . . H18 H 1.0677(12) 0.7447(13) 0.6211(5) 0.189 Uiso 1 calc R . C19 C 1.0234(9) 0.9326(14) 0.5928(4) 0.142(5) Uani 1 d . . H19 H 1.1039(9) 0.9412(14) 0.5725(4) 0.171 Uiso 1 calc R . C20 C 0.9230(7) 1.0376(8) 0.5932(2) 0.092(2) Uani 1 d . . H20 H 0.9335(7) 1.1143(8) 0.5719(2) 0.111 Uiso 1 calc R . C21 C 0.3950(5) 0.9640(6) 0.6407(2) 0.0627(14) Uani 1 d . . C22 C 0.3240(7) 1.0770(6) 0.6616(2) 0.085(2) Uani 1 d . . H22 H 0.3355(7) 1.1634(6) 0.6463(2) 0.102 Uiso 1 calc R . C23 C 0.2380(7) 1.0647(8) 0.7038(2) 0.092(2) Uani 1 d . . H23 H 0.1931(7) 1.1421(8) 0.7175(2) 0.111 Uiso 1 calc R . C24 C 0.2191(6) 0.9397(9) 0.7255(2) 0.085(2) Uani 1 d . . C25 C 0.2878(7) 0.8258(8) 0.7068(2) 0.087(2) Uani 1 d . . H25 H 0.2758(7) 0.7403(8) 0.7227(2) 0.105 Uiso 1 calc R . C26 C 0.3745(6) 0.8382(6) 0.6645(2) 0.072(2) Uani 1 d . . H26 H 0.4201(6) 0.7603(6) 0.6516(2) 0.087 Uiso 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 Cl1 0.1035(13) 0.203(2) 0.0959(12) -0.0086(14) 0.0248(11) -0.014(2) N1 0.053(2) 0.058(3) 0.096(3) -0.003(3) -0.006(3) -0.006(3) O1 0.078(2) 0.053(2) 0.098(3) 0.001(2) 0.010(2) -0.003(2) C1 0.050(3) 0.052(3) 0.086(4) -0.008(3) 0.004(3) 0.013(3) N2 0.036(2) 0.051(2) 0.070(3) 0.003(2) -0.007(2) 0.007(2) O2 0.050(2) 0.055(2) 0.075(2) 0.005(2) -0.005(2) 0.005(2) C2 0.044(2) 0.048(3) 0.062(3) 0.001(3) 0.002(2) 0.007(2) O3 0.054(2) 0.048(2) 0.090(2) 0.011(2) -0.021(2) -0.006(2) C3 0.057(3) 0.051(3) 0.071(3) -0.006(3) -0.005(3) 0.008(3) C4 0.038(2) 0.047(3) 0.066(3) 0.004(3) -0.001(2) 0.009(2) C5 0.078(4) 0.060(3) 0.075(3) 0.009(3) -0.010(3) 0.008(3) C6 0.046(3) 0.059(3) 0.054(3) -0.006(3) -0.004(3) 0.003(3) C7 0.078(4) 0.044(3) 0.087(4) 0.011(3) -0.020(3) -0.005(3) C8 0.054(3) 0.053(3) 0.080(4) 0.010(3) 0.007(3) 0.009(3) C9 0.063(4) 0.083(5) 0.129(6) 0.012(5) 0.001(4) 0.013(3) C10 0.103(6) 0.104(6) 0.112(6) 0.020(5) 0.044(5) 0.018(5) C11 0.112(5) 0.117(6) 0.092(5) 0.013(4) 0.012(5) 0.025(6) C12 0.082(4) 0.130(6) 0.088(5) 0.012(5) -0.004(4) 0.013(5) C13 0.064(3) 0.098(4) 0.063(3) 0.014(3) 0.000(3) 0.019(3) C14 0.068(3) 0.075(4) 0.106(5) -0.016(4) -0.022(3) -0.004(3) C15 0.050(3) 0.075(4) 0.052(3) -0.003(3) -0.008(3) 0.001(3) C16 0.092(5) 0.106(5) 0.072(4) 0.005(4) -0.001(3) 0.007(5) C17 0.154(8) 0.115(7) 0.139(8) 0.011(6) -0.072(7) 0.017(8) C18 0.100(8) 0.147(10) 0.227(15) -0.097(10) -0.083(9) 0.043(9) C19 0.054(4) 0.232(13) 0.141(8) -0.114(9) 0.002(5) -0.005(8) C20 0.070(4) 0.135(6) 0.073(4) -0.002(4) 0.007(3) -0.021(5) C21 0.060(3) 0.066(3) 0.062(3) -0.010(3) -0.004(3) 0.006(3) C22 0.102(4) 0.075(4) 0.079(4) -0.008(4) 0.012(4) 0.010(4) C23 0.099(5) 0.093(6) 0.085(4) -0.023(4) 0.016(4) 0.010(4) C24 0.075(4) 0.112(6) 0.069(4) -0.014(4) 0.000(3) -0.009(4) C25 0.096(4) 0.093(5) 0.073(4) 0.007(4) -0.004(4) -0.013(4) C26 0.082(4) 0.060(4) 0.075(4) -0.001(3) -0.008(3) -0.001(3) _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 Cl1 C24 1.747(6) . ? N1 C1 1.355(7) . ? N1 C14 1.457(6) . ? N1 C3 1.462(6) . ? O1 C1 1.204(6) . ? C1 C2 1.540(7) . ? N2 C6 1.346(5) . ? N2 C4 1.444(5) . ? N2 H2 0.86 . ? O2 C6 1.226(5) . ? C2 C4 1.511(6) . ? C2 C3 1.562(6) . ? C2 H2A 0.98 . ? O3 C6 1.341(5) . ? O3 C7 1.449(6) . ? C3 C21 1.497(7) . ? C3 H3 0.98 . ? C4 C5 1.511(6) . ? C4 H4 0.98 . ? C5 H5A 0.96 . ? C5 H5B 0.96 . ? C5 H5C 0.96 . ? C7 C8 1.482(7) . ? C7 H7A 0.97 . ? C7 H7B 0.97 . ? C8 C13 1.370(7) . ? C8 C9 1.392(7) . ? C9 C10 1.392(9) . ? C9 H9 0.93 . ? C10 C11 1.343(9) . ? C10 H10 0.93 . ? C11 C12 1.323(8) . ? C11 H11 0.93 . ? C12 C13 1.368(7) . ? C12 H12 0.93 . ? C13 H13 0.93 . ? C14 C15 1.496(7) . ? C14 H14A 0.97 . ? C14 H14B 0.97 . ? C15 C20 1.356(7) . ? C15 C16 1.370(8) . ? C16 C17 1.354(10) . ? C16 H16 0.93 . ? C17 C18 1.324(13) . ? C17 H17 0.93 . ? C18 C19 1.368(14) . ? C18 H18 0.93 . ? C19 C20 1.393(12) . ? C19 H19 0.93 . ? C20 H20 0.93 . ? C21 C26 1.377(7) . ? C21 C22 1.392(7) . ? C22 C23 1.366(8) . ? C22 H22 0.93 . ? C23 C24 1.344(8) . ? C23 H23 0.93 . ? C24 C25 1.369(8) . ? C25 C26 1.371(7) . ? C25 H25 0.93 . ? C26 H26 0.93 . ? 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 C1 N1 C14 132.9(5) . . ? C1 N1 C3 96.1(4) . . ? C14 N1 C3 129.8(5) . . ? O1 C1 N1 132.5(5) . . ? O1 C1 C2 135.9(5) . . ? N1 C1 C2 91.6(4) . . ? C6 N2 C4 122.9(4) . . ? C6 N2 H2 118.6(3) . . ? C4 N2 H2 118.6(2) . . ? C4 C2 C1 117.6(4) . . ? C4 C2 C3 118.9(4) . . ? C1 C2 C3 85.0(4) . . ? C4 C2 H2A 111.0(2) . . ? C1 C2 H2A 111.0(2) . . ? C3 C2 H2A 111.0(2) . . ? C6 O3 C7 116.4(4) . . ? N1 C3 C21 116.3(4) . . ? N1 C3 C2 86.7(4) . . ? C21 C3 C2 119.7(4) . . ? N1 C3 H3 110.7(2) . . ? C21 C3 H3 110.7(3) . . ? C2 C3 H3 110.7(2) . . ? N2 C4 C2 111.3(4) . . ? N2 C4 C5 110.0(4) . . ? C2 C4 C5 110.8(4) . . ? N2 C4 H4 108.2(2) . . ? C2 C4 H4 108.2(2) . . ? C5 C4 H4 108.2(3) . . ? C4 C5 H5A 109.5(3) . . ? C4 C5 H5B 109.5(3) . . ? H5A C5 H5B 109.5 . . ? C4 C5 H5C 109.5(3) . . ? H5A C5 H5C 109.5 . . ? H5B C5 H5C 109.5 . . ? O2 C6 O3 123.9(5) . . ? O2 C6 N2 124.7(5) . . ? O3 C6 N2 111.4(4) . . ? O3 C7 C8 112.5(5) . . ? O3 C7 H7A 109.1(3) . . ? C8 C7 H7A 109.1(3) . . ? O3 C7 H7B 109.1(2) . . ? C8 C7 H7B 109.1(3) . . ? H7A C7 H7B 107.8 . . ? C13 C8 C9 117.0(5) . . ? C13 C8 C7 120.4(5) . . ? C9 C8 C7 122.6(5) . . ? C10 C9 C8 120.0(6) . . ? C10 C9 H9 120.0(4) . . ? C8 C9 H9 120.0(3) . . ? C11 C10 C9 120.0(6) . . ? C11 C10 H10 120.0(5) . . ? C9 C10 H10 120.0(4) . . ? C12 C11 C10 120.8(7) . . ? C12 C11 H11 119.6(4) . . ? C10 C11 H11 119.6(5) . . ? C11 C12 C13 120.7(6) . . ? C11 C12 H12 119.7(4) . . ? C13 C12 H12 119.7(4) . . ? C8 C13 C12 121.5(5) . . ? C8 C13 H13 119.2(3) . . ? C12 C13 H13 119.2(4) . . ? N1 C14 C15 112.6(4) . . ? N1 C14 H14A 109.1(3) . . ? C15 C14 H14A 109.1(3) . . ? N1 C14 H14B 109.1(3) . . ? C15 C14 H14B 109.1(3) . . ? H14A C14 H14B 107.8 . . ? C20 C15 C16 119.0(6) . . ? C20 C15 C14 121.2(6) . . ? C16 C15 C14 119.7(5) . . ? C17 C16 C15 120.5(7) . . ? C17 C16 H16 119.7(6) . . ? C15 C16 H16 119.7(4) . . ? C18 C17 C16 121.5(11) . . ? C18 C17 H17 119.3(8) . . ? C16 C17 H17 119.3(6) . . ? C17 C18 C19 119.7(12) . . ? C17 C18 H18 120.2(8) . . ? C19 C18 H18 120.2(8) . . ? C18 C19 C20 119.7(10) . . ? C18 C19 H19 120.2(8) . . ? C20 C19 H19 120.2(6) . . ? C15 C20 C19 119.6(8) . . ? C15 C20 H20 120.2(4) . . ? C19 C20 H20 120.2(6) . . ? C26 C21 C22 117.0(5) . . ? C26 C21 C3 121.4(5) . . ? C22 C21 C3 121.6(5) . . ? C23 C22 C21 121.9(6) . . ? C23 C22 H22 119.0(4) . . ? C21 C22 H22 119.0(3) . . ? C24 C23 C22 119.3(6) . . ? C24 C23 H23 120.3(4) . . ? C22 C23 H23 120.3(4) . . ? C23 C24 C25 120.9(6) . . ? C23 C24 Cl1 120.4(6) . . ? C25 C24 Cl1 118.7(6) . . ? C26 C25 C24 119.7(6) . . ? C26 C25 H25 120.1(4) . . ? C24 C25 H25 120.1(4) . . ? C25 C26 C21 121.1(6) . . ? C25 C26 H26 119.5(4) . . ? C21 C26 H26 119.5(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 C14 N1 C1 O1 -4.2(9) . . . . ? C3 N1 C1 O1 -172.5(6) . . . . ? C14 N1 C1 C2 174.1(5) . . . . ? C3 N1 C1 C2 5.8(4) . . . . ? O1 C1 C2 C4 52.5(7) . . . . ? N1 C1 C2 C4 -125.6(4) . . . . ? O1 C1 C2 C3 172.7(6) . . . . ? N1 C1 C2 C3 -5.4(3) . . . . ? C1 N1 C3 C21 -127.4(5) . . . . ? C14 N1 C3 C21 63.7(7) . . . . ? C1 N1 C3 C2 -5.7(4) . . . . ? C14 N1 C3 C2 -174.6(5) . . . . ? C4 C2 C3 N1 124.0(4) . . . . ? C1 C2 C3 N1 5.0(3) . . . . ? C4 C2 C3 C21 -117.5(5) . . . . ? C1 C2 C3 C21 123.6(5) . . . . ? C6 N2 C4 C2 -95.1(5) . . . . ? C6 N2 C4 C5 141.7(4) . . . . ? C1 C2 C4 N2 162.9(4) . . . . ? C3 C2 C4 N2 62.6(5) . . . . ? C1 C2 C4 C5 -74.4(5) . . . . ? C3 C2 C4 C5 -174.6(4) . . . . ? C7 O3 C6 O2 0.0(7) . . . . ? C7 O3 C6 N2 -179.5(4) . . . . ? C4 N2 C6 O2 -0.4(7) . . . . ? C4 N2 C6 O3 179.1(3) . . . . ? C6 O3 C7 C8 81.4(6) . . . . ? O3 C7 C8 C13 -103.9(6) . . . . ? O3 C7 C8 C9 75.6(7) . . . . ? C13 C8 C9 C10 -1.3(10) . . . . ? C7 C8 C9 C10 179.1(6) . . . . ? C8 C9 C10 C11 1.8(12) . . . . ? C9 C10 C11 C12 -2.0(13) . . . . ? C10 C11 C12 C13 1.8(12) . . . . ? C9 C8 C13 C12 1.1(9) . . . . ? C7 C8 C13 C12 -179.3(6) . . . . ? C11 C12 C13 C8 -1.4(11) . . . . ? C1 N1 C14 C15 -105.5(6) . . . . ? C3 N1 C14 C15 59.2(7) . . . . ? N1 C14 C15 C20 95.3(6) . . . . ? N1 C14 C15 C16 -80.4(7) . . . . ? C20 C15 C16 C17 -0.7(9) . . . . ? C14 C15 C16 C17 175.1(6) . . . . ? C15 C16 C17 C18 1.2(12) . . . . ? C16 C17 C18 C19 0.5(15) . . . . ? C17 C18 C19 C20 -2.8(15) . . . . ? C16 C15 C20 C19 -1.6(9) . . . . ? C14 C15 C20 C19 -177.3(6) . . . . ? C18 C19 C20 C15 3.3(12) . . . . ? N1 C3 C21 C26 -138.4(5) . . . . ? C2 C3 C21 C26 119.5(5) . . . . ? N1 C3 C21 C22 44.0(7) . . . . ? C2 C3 C21 C22 -58.1(7) . . . . ? C26 C21 C22 C23 0.2(9) . . . . ? C3 C21 C22 C23 177.9(5) . . . . ? C21 C22 C23 C24 -1.2(10) . . . . ? C22 C23 C24 C25 1.9(10) . . . . ? C22 C23 C24 Cl1 -178.9(4) . . . . ? C23 C24 C25 C26 -1.7(9) . . . . ? Cl1 C24 C25 C26 179.1(4) . . . . ? C24 C25 C26 C21 0.7(8) . . . . ? C22 C21 C26 C25 0.0(8) . . . . ? C3 C21 C26 C25 -177.7(5) . . . . ? _refine_diff_density_max 0.136 _refine_diff_density_min -0.176 _refine_diff_density_rms 0.033 data_s545rm _database_code_CSD 165008 _publ_contact_author ' Joachim Podlech' _publ_contact_author_email joachim.podlech@po.uni-stuttgart.de loop_ _publ_author_name 'Michael R. Linder' 'Wolfgang U. Frey' 'Joachim Podlech' _journal_name_full 'Journal of the Chemical Society, Perkin Transactions 1' _journal_coden_Cambridge 207 _audit_creation_method SHELXL _chemical_name_systematic ; (3S,4R,1'S)-1-Benzyl-3-[1-(benzyloxycarbonylamino)ethyl]-4- (4-nitrophenyl)-azetidin-2-one # The configuration has been determined relative to the configuration at 1' # which is given by the synthetic precursors ; _chemical_name_common ? _chemical_formula_moiety ? _chemical_formula_structural ? _chemical_formula_analytical ? _chemical_formula_sum 'C26 H25 N3 O5' _chemical_formula_weight 459.49 _chemical_melting_point '433 - 434 K' _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' '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' _symmetry_cell_setting orthorhombic _symmetry_space_group_name_H-M P2(1)2(1)2(1) 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 9.312(2) _cell_length_b 9.733(2) _cell_length_c 26.550(6) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 2406.3(9) _cell_formula_units_Z 4 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 26 _cell_measurement_theta_min 12 _cell_measurement_theta_max 14 _exptl_crystal_description plates _exptl_crystal_colour colourless _exptl_crystal_size_max 0.75 _exptl_crystal_size_mid 0.60 _exptl_crystal_size_min 0.20 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.268 _exptl_crystal_density_method ? _exptl_crystal_F_000 968 _exptl_absorpt_coefficient_mu 0.089 _exptl_absorpt_correction_type ? _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 293(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device Nicolet P3 _diffrn_measurement_method Wyckoff - Scan _diffrn_standards_number 3 _diffrn_standards_interval_count 50 _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 3146 _diffrn_reflns_av_R_equivalents 0.0000 _diffrn_reflns_av_sigmaI/netI 0.0397 _diffrn_reflns_limit_h_min 0 _diffrn_reflns_limit_h_max 12 _diffrn_reflns_limit_k_min 0 _diffrn_reflns_limit_k_max 12 _diffrn_reflns_limit_l_min 0 _diffrn_reflns_limit_l_max 34 _diffrn_reflns_theta_min 1.53 _diffrn_reflns_theta_max 27.50 _reflns_number_total 3146 _reflns_number_observed 1837 _reflns_observed_criterion >2sigma(I) _computing_data_collection Siemens P3/V Data Collection System _computing_cell_refinement Siemens P3/V Data Collection System _computing_data_reduction SHELXTL plus - XDISK _computing_structure_solution 'SHELXS-86 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-93 (Sheldrick, 1993)' _computing_molecular_graphics SHELXTL - XP _computing_publication_material ? _refine_special_details ; Refinement on F^2^ for ALL reflections except for 419 with very negative F^2^ or flagged by the user for potential systematic errors. Weighted R-factors wR and all goodnesses 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 observed criterion of F^2^ > 2sigma(F^2^) is used only for calculating _R_factor_obs 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 w=1/[\s^2^(Fo^2^)+(0.0385P)^2^+0.7171P] 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 ? _refine_ls_extinction_method SHELXL _refine_ls_extinction_coef 0.0112(11) _refine_ls_extinction_expression 'Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^' _refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _refine_ls_abs_structure_Flack 0.52(238) _refine_ls_number_reflns 2727 _refine_ls_number_parameters 308 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.1101 _refine_ls_R_factor_obs 0.0545 _refine_ls_wR_factor_all 0.1412 _refine_ls_wR_factor_obs 0.1060 _refine_ls_goodness_of_fit_all 1.037 _refine_ls_goodness_of_fit_obs 1.155 _refine_ls_restrained_S_all 1.136 _refine_ls_restrained_S_obs 1.155 _refine_ls_shift/esd_max 0.001 _refine_ls_shift/esd_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_thermal_displace_type _atom_site_occupancy _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_group O1 O -0.0965(3) -0.2361(3) 0.01417(12) 0.0814(9) Uani 1 d . . C1 C -0.0522(4) -0.1471(4) 0.0419(2) 0.0641(11) Uani 1 d . . N1 N -0.0957(4) -0.1067(3) 0.0883(2) 0.0758(10) Uani 1 d . . O2 O -0.0355(3) 0.3203(3) 0.03044(9) 0.0578(7) Uani 1 d . . N2 N 0.1495(3) 0.1835(3) 0.00550(11) 0.0516(7) Uani 1 d . . H2 H 0.2408(3) 0.1797(3) 0.00088(11) 0.062 Uiso 1 calc R . C2 C 0.0628(4) -0.0356(3) 0.03995(14) 0.0566(9) Uani 1 d . . H2A H 0.1584(4) -0.0748(3) 0.04544(14) 0.068 Uiso 1 calc R . O3 O 0.1943(3) 0.3970(2) 0.02921(10) 0.0622(7) Uani 1 d . . C3 C -0.0033(4) 0.0162(4) 0.09062(15) 0.0622(11) Uani 1 d . . H3 H -0.0597(4) 0.1000(4) 0.08534(15) 0.075 Uiso 1 calc R . C4 C 0.0635(4) 0.0621(3) -0.00483(13) 0.0522(9) Uani 1 d . . H4 H -0.0354(4) 0.0913(3) -0.01144(13) 0.063 Uiso 1 calc R . C5 C 0.1201(5) -0.0119(4) -0.05142(15) 0.0682(11) Uani 1 d . . H5A H 0.1203(5) 0.0502(4) -0.07951(15) 0.102 Uiso 1 calc R . H5B H 0.0595(5) -0.0890(4) -0.05888(15) 0.102 Uiso 1 calc R . H5C H 0.2162(5) -0.0434(4) -0.04520(15) 0.102 Uiso 1 calc R . C6 C 0.0914(4) 0.3009(4) 0.02194(13) 0.0476(8) Uani 1 d . . C7 C 0.1445(5) 0.5301(4) 0.0470(2) 0.0678(11) Uani 1 d . . H7A H 0.0529(5) 0.5509(4) 0.0313(2) 0.081 Uiso 1 calc R . H7B H 0.2125(5) 0.6002(4) 0.0368(2) 0.081 Uiso 1 calc R . C8 C 0.1275(4) 0.5340(4) 0.1031(2) 0.0606(10) Uani 1 d . . C9 C 0.2442(5) 0.5438(5) 0.1359(2) 0.0856(14) Uani 1 d . . H9 H 0.3369(5) 0.5467(5) 0.1230(2) 0.103 Uiso 1 calc R . C10 C 0.2233(8) 0.5493(6) 0.1875(2) 0.106(2) Uani 1 d . . H10 H 0.3018(8) 0.5563(6) 0.2090(2) 0.127 Uiso 1 calc R . C11 C 0.0904(9) 0.5447(7) 0.2064(2) 0.124(2) Uani 1 d . . H11 H 0.0768(9) 0.5490(7) 0.2411(2) 0.148 Uiso 1 calc R . C12 C -0.0239(7) 0.5338(8) 0.1756(2) 0.120(2) Uani 1 d . . H12 H -0.1159(7) 0.5300(8) 0.1892(2) 0.144 Uiso 1 calc R . C13 C -0.0059(5) 0.5280(6) 0.1240(2) 0.0865(15) Uani 1 d . . H13 H -0.0859(5) 0.5200(6) 0.1033(2) 0.104 Uiso 1 calc R . C14 C -0.2171(5) -0.1441(5) 0.1204(2) 0.093(2) Uani 1 d . . H14A H -0.1825(5) -0.1641(5) 0.1541(2) 0.111 Uiso 1 calc R . H14B H -0.2623(5) -0.2264(5) 0.1073(2) 0.111 Uiso 1 calc R . C15 C -0.3255(4) -0.0312(4) 0.12298(15) 0.0617(10) Uani 1 d . . C16 C -0.3102(6) 0.0719(6) 0.1567(2) 0.102(2) Uani 1 d . . H16 H -0.2357(6) 0.0669(6) 0.1800(2) 0.122 Uiso 1 calc R . C17 C -0.3996(11) 0.1826(9) 0.1580(4) 0.182(5) Uani 1 d . . H17 H -0.3865(11) 0.2529(9) 0.1813(4) 0.218 Uiso 1 calc R . C18 C -0.5047(14) 0.1869(13) 0.1252(6) 0.220(10) Uani 1 d . . H18 H -0.5647(14) 0.2633(13) 0.1254(6) 0.264 Uiso 1 calc R . C19 C -0.5309(10) 0.0875(14) 0.0914(3) 0.183(6) Uani 1 d . . H19 H -0.6089(10) 0.0930(14) 0.0696(3) 0.220 Uiso 1 calc R . C20 C -0.4362(5) -0.0255(9) 0.0901(2) 0.112(2) Uani 1 d . . H20 H -0.4497(5) -0.0955(9) 0.0667(2) 0.134 Uiso 1 calc R . C21 C 0.0909(5) 0.0296(4) 0.1363(2) 0.0650(11) Uani 1 d . . C22 C 0.1079(5) 0.1558(4) 0.1595(2) 0.0750(13) Uani 1 d . . H22 H 0.0568(5) 0.2311(4) 0.1475(2) 0.090 Uiso 1 calc R . C23 C 0.1994(6) 0.1725(5) 0.2002(2) 0.0853(14) Uani 1 d . . H23 H 0.2103(6) 0.2578(5) 0.2154(2) 0.102 Uiso 1 calc R . C24 C 0.2733(5) 0.0601(6) 0.2173(2) 0.0815(14) Uani 1 d . . C25 C 0.2592(6) -0.0656(6) 0.1961(2) 0.090(2) Uani 1 d . . H25 H 0.3106(6) -0.1403(6) 0.2084(2) 0.108 Uiso 1 calc R . C26 C 0.1663(6) -0.0810(5) 0.1554(2) 0.0844(14) Uani 1 d . . H26 H 0.1547(6) -0.1672(5) 0.1409(2) 0.101 Uiso 1 calc R . N3 N 0.3732(6) 0.0772(7) 0.2607(2) 0.108(2) Uani 1 d . . O4 O 0.4325(6) -0.0243(6) 0.2763(2) 0.164(2) Uani 1 d . . O5 O 0.3897(6) 0.1921(7) 0.2773(2) 0.153(2) Uani 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 O1 0.082(2) 0.0448(14) 0.117(3) -0.006(2) -0.009(2) -0.001(2) C1 0.057(2) 0.041(2) 0.095(3) 0.005(2) 0.006(2) 0.010(2) N1 0.064(2) 0.052(2) 0.111(3) 0.004(2) 0.021(2) -0.006(2) O2 0.0435(14) 0.0544(14) 0.075(2) -0.0066(14) 0.0049(13) 0.0105(12) N2 0.0384(15) 0.0437(15) 0.073(2) -0.005(2) 0.0025(14) 0.0038(14) C2 0.051(2) 0.043(2) 0.076(2) 0.001(2) 0.004(2) 0.006(2) O3 0.0531(14) 0.0473(13) 0.086(2) -0.0151(14) 0.0150(14) -0.0045(13) C3 0.067(2) 0.042(2) 0.077(3) 0.004(2) 0.011(2) 0.003(2) C4 0.043(2) 0.044(2) 0.070(2) -0.005(2) 0.002(2) 0.006(2) C5 0.072(2) 0.055(2) 0.078(3) -0.011(2) 0.003(2) 0.011(2) C6 0.046(2) 0.044(2) 0.054(2) 0.001(2) 0.002(2) 0.005(2) C7 0.075(3) 0.044(2) 0.084(3) -0.005(2) 0.013(2) -0.006(2) C8 0.057(2) 0.046(2) 0.078(3) -0.013(2) -0.006(2) 0.010(2) C9 0.067(3) 0.069(3) 0.121(4) -0.014(3) -0.012(3) 0.014(2) C10 0.119(5) 0.094(4) 0.104(5) -0.023(4) -0.050(4) 0.030(4) C11 0.150(6) 0.142(6) 0.080(4) -0.018(4) -0.019(4) 0.056(5) C12 0.111(4) 0.171(6) 0.077(3) -0.014(4) 0.005(3) 0.047(5) C13 0.070(3) 0.115(4) 0.075(3) -0.022(3) -0.002(3) 0.023(3) C14 0.082(3) 0.067(3) 0.129(4) 0.017(3) 0.031(3) 0.000(3) C15 0.059(2) 0.066(2) 0.060(2) 0.011(2) 0.009(2) -0.009(2) C16 0.099(4) 0.112(4) 0.094(4) -0.031(4) 0.023(3) -0.012(4) C17 0.202(10) 0.101(6) 0.243(12) -0.055(7) 0.150(10) -0.023(7) C18 0.150(12) 0.151(9) 0.358(23) 0.144(12) 0.154(14) 0.063(10) C19 0.070(4) 0.331(17) 0.149(7) 0.162(9) 0.011(5) 0.023(9) C20 0.062(3) 0.208(7) 0.064(3) 0.015(4) 0.004(3) -0.017(4) C21 0.074(3) 0.050(2) 0.071(3) 0.006(2) 0.014(2) 0.000(2) C22 0.091(3) 0.058(3) 0.076(3) 0.006(2) 0.018(3) 0.002(3) C23 0.101(4) 0.076(3) 0.079(3) -0.002(3) 0.014(3) -0.005(3) C24 0.082(3) 0.091(4) 0.072(3) 0.011(3) 0.007(3) -0.019(3) C25 0.099(4) 0.083(4) 0.089(3) 0.027(3) -0.014(3) 0.002(3) C26 0.101(4) 0.052(2) 0.100(4) 0.008(3) -0.001(3) 0.006(3) N3 0.103(4) 0.133(5) 0.089(3) 0.019(4) 0.001(3) -0.031(4) O4 0.167(5) 0.148(4) 0.178(5) 0.051(4) -0.079(4) -0.037(4) O5 0.156(4) 0.173(4) 0.129(4) -0.042(4) -0.024(3) -0.014(4) _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 O1 C1 1.210(5) . ? C1 N1 1.353(5) . ? C1 C2 1.525(5) . ? N1 C14 1.463(5) . ? N1 C3 1.474(5) . ? O2 C6 1.217(4) . ? N2 C6 1.338(4) . ? N2 C4 1.453(4) . ? N2 H2 0.86 . ? C2 C4 1.522(5) . ? C2 C3 1.563(5) . ? C2 H2A 0.98 . ? O3 C6 1.353(4) . ? O3 C7 1.455(4) . ? C3 C21 1.502(6) . ? C3 H3 0.98 . ? C4 C5 1.525(5) . ? C4 H4 0.98 . ? C5 H5A 0.96 . ? C5 H5B 0.96 . ? C5 H5C 0.96 . ? C7 C8 1.500(5) . ? C7 H7A 0.97 . ? C7 H7B 0.97 . ? C8 C13 1.362(6) . ? C8 C9 1.396(6) . ? C9 C10 1.383(7) . ? C9 H9 0.93 . ? C10 C11 1.337(8) . ? C10 H10 0.93 . ? C11 C12 1.347(8) . ? C11 H11 0.93 . ? C12 C13 1.380(6) . ? C12 H12 0.93 . ? C13 H13 0.93 . ? C14 C15 1.493(6) . ? C14 H14A 0.97 . ? C14 H14B 0.97 . ? C15 C20 1.353(6) . ? C15 C16 1.353(6) . ? C16 C17 1.363(10) . ? C16 H16 0.93 . ? C17 C18 1.31(2) . ? C17 H17 0.93 . ? C18 C19 1.34(2) . ? C18 H18 0.93 . ? C19 C20 1.410(12) . ? C19 H19 0.93 . ? C20 H20 0.93 . ? C21 C26 1.382(6) . ? C21 C22 1.383(6) . ? C22 C23 1.385(6) . ? C22 H22 0.93 . ? C23 C24 1.370(7) . ? C23 H23 0.93 . ? C24 C25 1.354(7) . ? C24 N3 1.488(7) . ? C25 C26 1.391(6) . ? C25 H25 0.93 . ? C26 H26 0.93 . ? N3 O4 1.205(7) . ? N3 O5 1.213(7) . ? 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 N1 131.3(4) . . ? O1 C1 C2 136.7(4) . . ? N1 C1 C2 92.0(3) . . ? C1 N1 C14 133.6(4) . . ? C1 N1 C3 95.7(3) . . ? C14 N1 C3 128.9(4) . . ? C6 N2 C4 122.2(3) . . ? C6 N2 H2 118.9(2) . . ? C4 N2 H2 118.9(2) . . ? C4 C2 C1 118.3(3) . . ? C4 C2 C3 118.2(3) . . ? C1 C2 C3 85.6(3) . . ? C4 C2 H2A 110.8(2) . . ? C1 C2 H2A 110.8(2) . . ? C3 C2 H2A 110.8(2) . . ? C6 O3 C7 115.8(3) . . ? N1 C3 C21 116.4(3) . . ? N1 C3 C2 86.1(3) . . ? C21 C3 C2 119.5(3) . . ? N1 C3 H3 110.9(2) . . ? C21 C3 H3 110.9(2) . . ? C2 C3 H3 110.9(2) . . ? N2 C4 C2 111.3(3) . . ? N2 C4 C5 110.3(3) . . ? C2 C4 C5 109.9(3) . . ? N2 C4 H4 108.4(2) . . ? C2 C4 H4 108.4(2) . . ? C5 C4 H4 108.4(2) . . ? C4 C5 H5A 109.5(2) . . ? C4 C5 H5B 109.5(2) . . ? H5A C5 H5B 109.5 . . ? C4 C5 H5C 109.5(2) . . ? H5A C5 H5C 109.5 . . ? H5B C5 H5C 109.5 . . ? O2 C6 N2 125.8(3) . . ? O2 C6 O3 123.7(3) . . ? N2 C6 O3 110.5(3) . . ? O3 C7 C8 112.2(3) . . ? O3 C7 H7A 109.2(2) . . ? C8 C7 H7A 109.2(2) . . ? O3 C7 H7B 109.2(2) . . ? C8 C7 H7B 109.2(2) . . ? H7A C7 H7B 107.9 . . ? C13 C8 C9 117.2(4) . . ? C13 C8 C7 120.0(4) . . ? C9 C8 C7 122.7(4) . . ? C10 C9 C8 120.7(5) . . ? C10 C9 H9 119.6(4) . . ? C8 C9 H9 119.6(3) . . ? C11 C10 C9 120.1(5) . . ? C11 C10 H10 120.0(4) . . ? C9 C10 H10 120.0(4) . . ? C10 C11 C12 120.4(6) . . ? C10 C11 H11 119.8(4) . . ? C12 C11 H11 119.8(4) . . ? C11 C12 C13 120.6(6) . . ? C11 C12 H12 119.7(4) . . ? C13 C12 H12 119.7(4) . . ? C8 C13 C12 120.9(5) . . ? C8 C13 H13 119.5(3) . . ? C12 C13 H13 119.5(4) . . ? N1 C14 C15 111.5(3) . . ? N1 C14 H14A 109.3(3) . . ? C15 C14 H14A 109.3(3) . . ? N1 C14 H14B 109.3(3) . . ? C15 C14 H14B 109.3(3) . . ? H14A C14 H14B 108.0 . . ? C20 C15 C16 118.6(5) . . ? C20 C15 C14 121.1(5) . . ? C16 C15 C14 120.3(5) . . ? C15 C16 C17 122.5(7) . . ? C15 C16 H16 118.7(3) . . ? C17 C16 H16 118.7(6) . . ? C18 C17 C16 117.8(11) . . ? C18 C17 H17 121.1(8) . . ? C16 C17 H17 121.1(6) . . ? C17 C18 C19 123.9(12) . . ? C17 C18 H18 118.1(8) . . ? C19 C18 H18 118.1(8) . . ? C18 C19 C20 117.7(10) . . ? C18 C19 H19 121.2(8) . . ? C20 C19 H19 121.2(6) . . ? C15 C20 C19 119.5(7) . . ? C15 C20 H20 120.2(4) . . ? C19 C20 H20 120.2(6) . . ? C26 C21 C22 118.0(4) . . ? C26 C21 C3 121.8(4) . . ? C22 C21 C3 120.2(4) . . ? C21 C22 C23 121.5(5) . . ? C21 C22 H22 119.3(3) . . ? C23 C22 H22 119.3(3) . . ? C24 C23 C22 118.4(5) . . ? C24 C23 H23 120.8(3) . . ? C22 C23 H23 120.8(3) . . ? C25 C24 C23 122.2(5) . . ? C25 C24 N3 118.9(5) . . ? C23 C24 N3 118.8(5) . . ? C24 C25 C26 118.8(5) . . ? C24 C25 H25 120.6(3) . . ? C26 C25 H25 120.6(3) . . ? C21 C26 C25 121.2(4) . . ? C21 C26 H26 119.4(3) . . ? C25 C26 H26 119.4(3) . . ? O4 N3 O5 124.9(6) . . ? O4 N3 C24 117.4(6) . . ? O5 N3 C24 117.7(6) . . ? 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 C1 N1 C14 -6.5(7) . . . . ? C2 C1 N1 C14 171.4(4) . . . . ? O1 C1 N1 C3 -171.6(4) . . . . ? C2 C1 N1 C3 6.3(3) . . . . ? O1 C1 C2 C4 52.0(6) . . . . ? N1 C1 C2 C4 -125.7(3) . . . . ? O1 C1 C2 C3 171.7(5) . . . . ? N1 C1 C2 C3 -5.9(3) . . . . ? C1 N1 C3 C21 -127.3(4) . . . . ? C14 N1 C3 C21 66.6(5) . . . . ? C1 N1 C3 C2 -6.1(3) . . . . ? C14 N1 C3 C2 -172.3(4) . . . . ? C4 C2 C3 N1 125.3(3) . . . . ? C1 C2 C3 N1 5.4(3) . . . . ? C4 C2 C3 C21 -116.4(4) . . . . ? C1 C2 C3 C21 123.7(3) . . . . ? C6 N2 C4 C2 -96.1(4) . . . . ? C6 N2 C4 C5 141.7(3) . . . . ? C1 C2 C4 N2 163.5(3) . . . . ? C3 C2 C4 N2 62.5(4) . . . . ? C1 C2 C4 C5 -74.1(4) . . . . ? C3 C2 C4 C5 -175.1(3) . . . . ? C4 N2 C6 O2 0.6(6) . . . . ? C4 N2 C6 O3 179.2(3) . . . . ? C7 O3 C6 O2 -1.6(5) . . . . ? C7 O3 C6 N2 179.7(3) . . . . ? C6 O3 C7 C8 84.5(4) . . . . ? O3 C7 C8 C13 -104.1(5) . . . . ? O3 C7 C8 C9 75.9(5) . . . . ? C13 C8 C9 C10 -1.0(7) . . . . ? C7 C8 C9 C10 179.0(4) . . . . ? C8 C9 C10 C11 0.3(9) . . . . ? C9 C10 C11 C12 0.4(11) . . . . ? C10 C11 C12 C13 -0.4(11) . . . . ? C9 C8 C13 C12 1.0(8) . . . . ? C7 C8 C13 C12 -178.9(5) . . . . ? C11 C12 C13 C8 -0.4(10) . . . . ? C1 N1 C14 C15 -107.6(5) . . . . ? C3 N1 C14 C15 53.2(6) . . . . ? N1 C14 C15 C20 90.9(5) . . . . ? N1 C14 C15 C16 -85.5(5) . . . . ? C20 C15 C16 C17 -1.7(8) . . . . ? C14 C15 C16 C17 174.7(6) . . . . ? C15 C16 C17 C18 0.7(12) . . . . ? C16 C17 C18 C19 1.4(18) . . . . ? C17 C18 C19 C20 -2.4(18) . . . . ? C16 C15 C20 C19 0.7(7) . . . . ? C14 C15 C20 C19 -175.7(5) . . . . ? C18 C19 C20 C15 1.2(12) . . . . ? N1 C3 C21 C26 43.2(5) . . . . ? C2 C3 C21 C26 -57.9(5) . . . . ? N1 C3 C21 C22 -138.8(4) . . . . ? C2 C3 C21 C22 120.1(4) . . . . ? C26 C21 C22 C23 1.2(7) . . . . ? C3 C21 C22 C23 -176.9(4) . . . . ? C21 C22 C23 C24 -0.3(7) . . . . ? C22 C23 C24 C25 -0.3(7) . . . . ? C22 C23 C24 N3 179.3(4) . . . . ? C23 C24 C25 C26 -0.1(8) . . . . ? N3 C24 C25 C26 -179.7(4) . . . . ? C22 C21 C26 C25 -1.6(7) . . . . ? C3 C21 C26 C25 176.5(4) . . . . ? C24 C25 C26 C21 1.0(7) . . . . ? C25 C24 N3 O4 -3.3(8) . . . . ? C23 C24 N3 O4 177.1(5) . . . . ? C25 C24 N3 O5 176.2(6) . . . . ? C23 C24 N3 O5 -3.4(8) . . . . ? _refine_diff_density_max 0.153 _refine_diff_density_min -0.131 _refine_diff_density_rms 0.029 data_s563rm1 _database_code_CSD 165009 _publ_contact_author ' Joachim Podlech' _publ_contact_author_email joachim.podlech@po.uni-stuttgart.de loop_ _publ_author_name 'Michael R. Linder' 'Wolfgang U. Frey' 'Joachim Podlech' _journal_name_full 'Journal of the Chemical Society, Perkin Transactions 1' _journal_coden_Cambridge 207 _audit_creation_method SHELXL _chemical_name_systematic ; (3R,4S,1'S)-1-Benzyl-3-(1-benzyloxycarbonylamino)ethyl]-4-(2-furyl)- azetidin-2-one # The configuration has been determined relative to the configuration at 1' # which is given by the synthetic precursors ; _chemical_name_common ? _chemical_formula_moiety ? _chemical_formula_structural ? _chemical_formula_analytical ? _chemical_formula_sum 'C24 H24 N2 O4' _chemical_formula_weight 404.45 _chemical_melting_point '382 - 383 K' _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' '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' _symmetry_cell_setting tetragonal _symmetry_space_group_name_H-M P4(1) loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, z+1/2' '-y, x, z+1/4' 'y, -x, z+3/4' _cell_length_a 9.6260(10) _cell_length_b 9.6260(10) _cell_length_c 47.354(11) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 4387.8(12) _cell_formula_units_Z 8 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 23 _cell_measurement_theta_min 9 _cell_measurement_theta_max 13 _exptl_crystal_description block _exptl_crystal_colour colourless _exptl_crystal_size_max 0.50 _exptl_crystal_size_mid 0.35 _exptl_crystal_size_min 0.20 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.224 _exptl_crystal_density_method ? _exptl_crystal_F_000 1712 _exptl_absorpt_coefficient_mu 0.084 _exptl_absorpt_correction_type none _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 293(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device Nicolet P3 _diffrn_measurement_method Wyckoff - Scan _diffrn_standards_number 3 _diffrn_standards_interval_count 50 _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 3968 _diffrn_reflns_av_R_equivalents 0.0264 _diffrn_reflns_av_sigmaI/netI 0.0499 _diffrn_reflns_limit_h_min 0 _diffrn_reflns_limit_h_max 11 _diffrn_reflns_limit_k_min 0 _diffrn_reflns_limit_k_max 11 _diffrn_reflns_limit_l_min 0 _diffrn_reflns_limit_l_max 54 _diffrn_reflns_theta_min 1.29 _diffrn_reflns_theta_max 24.00 _reflns_number_total 3483 _reflns_number_observed 2435 _reflns_observed_criterion >2sigma(I) _computing_data_collection Siemens P3/V Data Collection System _computing_cell_refinement Siemens P3/V Data Collection System _computing_data_reduction SHELXTL plus - XDISK _computing_structure_solution 'SHELXS-86 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-93 (Sheldrick, 1993)' _computing_molecular_graphics SHELXTL - XP _computing_publication_material ? _refine_special_details ; Refinement on F^2^ for ALL reflections except for 235 with very negative F^2^ or flagged by the user for potential systematic errors. Weighted R-factors wR and all goodnesses 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 observed criterion of F^2^ > 2sigma(F^2^) is used only for calculating _R_factor_obs 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 w=1/[\s^2^(Fo^2^)+(0.0227P)^2^+0.9468P] 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 ? _refine_ls_extinction_method SHELXL _refine_ls_extinction_coef 0.0025(3) _refine_ls_extinction_expression 'Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^' _refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _refine_ls_abs_structure_Flack 0.44(269) _refine_ls_number_reflns 3248 _refine_ls_number_parameters 543 _refine_ls_number_restraints 1 _refine_ls_R_factor_all 0.0930 _refine_ls_R_factor_obs 0.0535 _refine_ls_wR_factor_all 0.1032 _refine_ls_wR_factor_obs 0.0859 _refine_ls_goodness_of_fit_all 1.107 _refine_ls_goodness_of_fit_obs 1.213 _refine_ls_restrained_S_all 1.170 _refine_ls_restrained_S_obs 1.212 _refine_ls_shift/esd_max -0.006 _refine_ls_shift/esd_mean 0.001 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_thermal_displace_type _atom_site_occupancy _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_group N1A N 0.4813(6) 0.6892(7) 0.05148(14) 0.061(2) Uani 1 d . . C1A C 0.3633(8) 0.7302(10) 0.0643(2) 0.066(2) Uani 1 d . . O1A O 0.2937(6) 0.8345(7) 0.06118(11) 0.082(2) Uani 1 d . . N2A N 0.4658(6) 0.6885(6) 0.12619(12) 0.058(2) Uani 1 d . . H2A H 0.4663(6) 0.7777(6) 0.12551(12) 0.069 Uiso 1 calc R . O2A O 0.5854(8) 0.4959(6) 0.13869(14) 0.098(2) Uani 1 d . . C2A C 0.3584(8) 0.5993(8) 0.0823(2) 0.058(2) Uani 1 d . . H2A1 H 0.2865(8) 0.5358(8) 0.0753(2) 0.069 Uiso 1 calc R . O3A O 0.6656(6) 0.7099(5) 0.14924(12) 0.075(2) Uani 1 d . . C3A C 0.5003(8) 0.5638(8) 0.0691(2) 0.060(2) Uani 1 d . . H3A H 0.5751(8) 0.5779(8) 0.0828(2) 0.071 Uiso 1 calc R . C4A C 0.3495(8) 0.6135(8) 0.1146(2) 0.061(2) Uani 1 d . . H4A H 0.3485(8) 0.5201(8) 0.1228(2) 0.074 Uiso 1 calc R . C5A C 0.2130(9) 0.6887(9) 0.1231(2) 0.078(3) Uani 1 d . . H5A1 H 0.2088(9) 0.6969(9) 0.1433(2) 0.117 Uiso 1 calc R . H5A2 H 0.1347(9) 0.6361(9) 0.1165(2) 0.117 Uiso 1 calc R . H5A3 H 0.2112(9) 0.7797(9) 0.1148(2) 0.117 Uiso 1 calc R . C6A C 0.5749(9) 0.6210(9) 0.1382(2) 0.065(2) Uani 1 d . . C7A C 0.7823(11) 0.6413(11) 0.1625(3) 0.132(5) Uani 1 d . . H7A1 H 0.8388(11) 0.5962(11) 0.1482(3) 0.159 Uiso 1 calc R . H7A2 H 0.7491(11) 0.5709(11) 0.1755(3) 0.159 Uiso 1 calc R . C8A C 0.8670(11) 0.7458(10) 0.1780(3) 0.080(3) Uani 1 d . . C9A C 0.8731(13) 0.7441(14) 0.2072(3) 0.125(4) Uani 1 d . . H9A H 0.8172(13) 0.6837(14) 0.2176(3) 0.150 Uiso 1 calc R . C10A C 0.9633(23) 0.8333(23) 0.2208(4) 0.202(11) Uani 1 d . . H10A H 0.9762(23) 0.8288(23) 0.2402(4) 0.243 Uiso 1 calc R . C11A C 1.0289(23) 0.9229(18) 0.2057(7) 0.193(14) Uani 1 d . . H11A H 1.0820(23) 0.9877(18) 0.2155(7) 0.232 Uiso 1 calc R . C12A C 1.0296(18) 0.9338(22) 0.1770(6) 0.183(11) Uani 1 d . . H12A H 1.0836(18) 0.9976(22) 0.1672(6) 0.219 Uiso 1 calc R . C13A C 0.9403(15) 0.8386(16) 0.1640(3) 0.116(4) Uani 1 d . . H13A H 0.9322(15) 0.8411(16) 0.1445(3) 0.139 Uiso 1 calc R . C14A C 0.5727(9) 0.7622(9) 0.0321(2) 0.072(2) Uani 1 d . . H14A H 0.5251(9) 0.8436(9) 0.0249(2) 0.086 Uiso 1 calc R . H14B H 0.5934(9) 0.7021(9) 0.0162(2) 0.086 Uiso 1 calc R . C15A C 0.7067(8) 0.8067(8) 0.0457(2) 0.053(2) Uani 1 d . . C16A C 0.7014(10) 0.8830(10) 0.0699(2) 0.087(3) Uani 1 d . . H16A H 0.6157(10) 0.9069(10) 0.0776(2) 0.104 Uiso 1 calc R . C17A C 0.8245(12) 0.9261(11) 0.0835(2) 0.105(3) Uani 1 d . . H17A H 0.8205(12) 0.9760(11) 0.1003(2) 0.126 Uiso 1 calc R . C18A C 0.9453(13) 0.8946(13) 0.0721(2) 0.110(4) Uani 1 d . . H18A H 1.0266(13) 0.9239(13) 0.0809(2) 0.132 Uiso 1 calc R . C19A C 0.9536(10) 0.8214(16) 0.0481(3) 0.114(4) Uani 1 d . . H19A H 1.0399(10) 0.7998(16) 0.0405(3) 0.137 Uiso 1 calc R . C20A C 0.8331(10) 0.7780(10) 0.0347(2) 0.086(3) Uani 1 d . . H20A H 0.8393(10) 0.7283(10) 0.0179(2) 0.103 Uiso 1 calc R . C21A C 0.5190(9) 0.4311(9) 0.0539(2) 0.059(2) Uani 1 d . . O4A O 0.4437(6) 0.4110(6) 0.03021(12) 0.073(2) Uani 1 d . . C22A C 0.5966(10) 0.3198(10) 0.0597(2) 0.081(3) Uani 1 d . . H22A H 0.6591(10) 0.3083(10) 0.0745(2) 0.097 Uiso 1 calc R . C23A C 0.5614(12) 0.2218(9) 0.0379(2) 0.088(3) Uani 1 d . . H23A H 0.5962(12) 0.1321(9) 0.0362(2) 0.105 Uiso 1 calc R . C24A C 0.4738(11) 0.2793(10) 0.0212(2) 0.086(3) Uani 1 d . . H24A H 0.4361(11) 0.2375(10) 0.0052(2) 0.104 Uiso 1 calc R . N1B N 0.5045(7) 0.1665(7) 0.21434(13) 0.062(2) Uani 1 d . . O1B O 0.6842(6) 0.3289(7) 0.20824(12) 0.083(2) Uani 1 d . . C1B C 0.6231(9) 0.2212(9) 0.2038(2) 0.061(2) Uani 1 d . . N2B N 0.5397(6) 0.1921(6) 0.13923(12) 0.055(2) Uani 1 d . . H2B H 0.5341(6) 0.2812(6) 0.13977(12) 0.066 Uiso 1 calc R . C2B C 0.6426(7) 0.0963(7) 0.18364(15) 0.051(2) Uani 1 d . . H2B1 H 0.7168(7) 0.0357(7) 0.19067(15) 0.061 Uiso 1 calc R . O2B O 0.4299(7) -0.0029(6) 0.12634(12) 0.080(2) Uani 1 d . . O3B O 0.3464(6) 0.2070(6) 0.11479(11) 0.074(2) Uani 1 d . . C3B C 0.5002(8) 0.0475(8) 0.1953(2) 0.059(2) Uani 1 d . . H3B H 0.4279(8) 0.0612(8) 0.1811(2) 0.071 Uiso 1 calc R . C4B C 0.6625(8) 0.1233(7) 0.1522(2) 0.057(2) Uani 1 d . . H4B H 0.6729(8) 0.0327(7) 0.1430(2) 0.069 Uiso 1 calc R . C5B C 0.7908(8) 0.2058(9) 0.1456(2) 0.075(2) Uani 1 d . . H5B1 H 0.7976(8) 0.2194(9) 0.1256(2) 0.112 Uiso 1 calc R . H5B2 H 0.8711(8) 0.1564(9) 0.1522(2) 0.112 Uiso 1 calc R . H5B3 H 0.7857(8) 0.2944(9) 0.1549(2) 0.112 Uiso 1 calc R . C6B C 0.4401(9) 0.1219(8) 0.1270(2) 0.059(2) Uani 1 d . . C7B C 0.2336(12) 0.1348(11) 0.1014(3) 0.117(4) Uani 1 d . . H7B1 H 0.1762(12) 0.0898(11) 0.1155(3) 0.140 Uiso 1 calc R . H7B2 H 0.2698(12) 0.0639(11) 0.0888(3) 0.140 Uiso 1 calc R . C8B C 0.1482(10) 0.2374(10) 0.0849(2) 0.074(3) Uani 1 d . . C9B C 0.0617(12) 0.3311(13) 0.0974(2) 0.101(3) Uani 1 d . . H9B H 0.0538(12) 0.3318(13) 0.1170(2) 0.122 Uiso 1 calc R . C10B C -0.0152(12) 0.4258(14) 0.0815(4) 0.118(4) Uani 1 d . . H10B H -0.0687(12) 0.4951(14) 0.0899(4) 0.142 Uiso 1 calc R . C11B C -0.0065(15) 0.4096(15) 0.0523(4) 0.129(6) Uani 1 d . . H11B H -0.0601(15) 0.4671(15) 0.0409(4) 0.155 Uiso 1 calc R . C12B C 0.0726(17) 0.3183(18) 0.0404(3) 0.139(5) Uani 1 d . . H12B H 0.0750(17) 0.3114(18) 0.0208(3) 0.167 Uiso 1 calc R . C13B C 0.1528(11) 0.2317(12) 0.0565(3) 0.111(4) Uani 1 d . . H13B H 0.2113(11) 0.1680(12) 0.0477(3) 0.133 Uiso 1 calc R . C14B C 0.4087(8) 0.2211(8) 0.2350(2) 0.061(2) Uani 1 d . . H14C H 0.4545(8) 0.2937(8) 0.2457(2) 0.073 Uiso 1 calc R . H14D H 0.3836(8) 0.1476(8) 0.2480(2) 0.073 Uiso 1 calc R . C15B C 0.2779(8) 0.2794(8) 0.2218(2) 0.058(2) Uani 1 d . . C16B C 0.2793(10) 0.3420(10) 0.1958(2) 0.089(3) Uani 1 d . . H16B H 0.3622(10) 0.3506(10) 0.1859(2) 0.106 Uiso 1 calc R . C17B C 0.1567(13) 0.3924(11) 0.1844(2) 0.116(4) Uani 1 d . . H17B H 0.1562(13) 0.4345(11) 0.1667(2) 0.140 Uiso 1 calc R . C18B C 0.0358(12) 0.3792(12) 0.1997(3) 0.108(4) Uani 1 d . . H18B H -0.0465(12) 0.4155(12) 0.1926(3) 0.129 Uiso 1 calc R . C19B C 0.0354(11) 0.3162(14) 0.2241(3) 0.108(4) Uani 1 d . . H19B H -0.0480(11) 0.3050(14) 0.2337(3) 0.129 Uiso 1 calc R . C20B C 0.1563(9) 0.2660(9) 0.2358(2) 0.078(3) Uani 1 d . . H20B H 0.1544(9) 0.2229(9) 0.2534(2) 0.094 Uiso 1 calc R . C21B C 0.4856(9) -0.0907(9) 0.2083(2) 0.062(2) Uani 1 d . . O4B O 0.5672(7) -0.1191(7) 0.23052(14) 0.105(2) Uani 1 d . . C22B C 0.4139(13) -0.1999(12) 0.2007(2) 0.106(4) Uani 1 d . . H22B H 0.3495(13) -0.2030(12) 0.1861(2) 0.127 Uiso 1 calc R . C23B C 0.4484(21) -0.3081(15) 0.2177(3) 0.154(7) Uani 1 d . . H23B H 0.4145(21) -0.3984(15) 0.2167(3) 0.184 Uiso 1 calc R . C24B C 0.5401(18) -0.2595(14) 0.2360(3) 0.153(7) Uani 1 d . . H24B H 0.5806(18) -0.3110(14) 0.2504(3) 0.184 Uiso 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 N1A 0.041(4) 0.058(4) 0.083(5) 0.005(4) 0.003(3) -0.001(3) C1A 0.040(5) 0.088(7) 0.071(6) -0.016(5) -0.018(4) -0.012(5) O1A 0.064(4) 0.102(5) 0.080(4) 0.016(4) -0.003(3) 0.025(4) N2A 0.065(4) 0.043(4) 0.065(4) -0.018(3) -0.004(3) 0.001(3) O2A 0.124(5) 0.049(3) 0.122(5) -0.014(4) -0.054(5) 0.015(4) C2A 0.055(5) 0.063(5) 0.055(5) -0.005(4) -0.009(4) -0.006(4) O3A 0.064(4) 0.056(3) 0.106(4) -0.031(3) -0.039(3) 0.014(3) C3A 0.047(4) 0.061(5) 0.071(5) -0.010(5) -0.009(4) -0.009(4) C4A 0.050(5) 0.062(5) 0.072(6) -0.001(4) -0.001(4) -0.002(4) C5A 0.066(6) 0.088(6) 0.080(6) -0.003(5) 0.013(5) 0.002(5) C6A 0.068(6) 0.069(6) 0.058(5) -0.002(5) -0.014(4) 0.012(5) C7A 0.128(9) 0.079(7) 0.191(11) -0.042(7) -0.116(9) 0.045(7) C8A 0.062(6) 0.075(7) 0.105(8) -0.024(6) -0.034(6) 0.023(5) C9A 0.117(10) 0.163(13) 0.096(9) 0.008(9) -0.005(8) 0.006(8) C10A 0.235(24) 0.221(21) 0.150(16) -0.119(16) -0.115(17) 0.071(18) C11A 0.128(16) 0.081(11) 0.370(40) -0.026(18) -0.083(22) 0.011(10) C12A 0.076(10) 0.135(15) 0.337(30) 0.090(20) 0.001(15) 0.029(9) C13A 0.087(9) 0.119(10) 0.143(10) -0.002(9) 0.002(9) 0.045(8) C14A 0.059(5) 0.090(6) 0.067(5) 0.000(5) 0.000(5) -0.003(5) C15A 0.053(5) 0.048(4) 0.057(5) 0.003(4) 0.006(4) -0.009(4) C16A 0.063(6) 0.096(7) 0.101(7) -0.024(6) 0.021(5) -0.014(5) C17A 0.103(9) 0.110(8) 0.103(8) -0.040(6) 0.011(7) -0.020(7) C18A 0.091(9) 0.155(11) 0.083(7) -0.020(8) -0.009(7) -0.040(8) C19A 0.035(5) 0.184(13) 0.123(10) 0.012(9) -0.001(6) -0.011(7) C20A 0.062(6) 0.116(8) 0.079(6) -0.022(6) 0.011(5) 0.016(6) C21A 0.059(5) 0.068(6) 0.049(5) -0.004(4) -0.001(4) 0.000(4) O4A 0.081(4) 0.073(4) 0.066(4) -0.004(3) -0.014(3) -0.009(3) C22A 0.082(6) 0.090(7) 0.070(6) 0.007(6) -0.013(5) 0.013(6) C23A 0.133(9) 0.063(6) 0.068(6) 0.004(5) 0.006(6) 0.009(6) C24A 0.119(9) 0.075(7) 0.065(6) -0.006(5) -0.006(6) -0.028(6) N1B 0.048(4) 0.073(4) 0.065(4) -0.010(4) 0.000(3) 0.013(4) O1B 0.071(4) 0.094(5) 0.085(4) -0.022(4) -0.002(3) -0.017(4) C1B 0.051(5) 0.070(6) 0.063(5) -0.007(4) -0.016(4) 0.011(4) N2B 0.058(4) 0.042(3) 0.065(4) -0.006(3) -0.021(3) 0.001(3) C2B 0.040(4) 0.059(5) 0.053(5) -0.005(4) -0.009(4) 0.019(4) O2B 0.096(4) 0.043(3) 0.102(5) -0.001(3) -0.034(4) -0.006(3) O3B 0.073(4) 0.057(3) 0.093(4) 0.007(3) -0.033(3) -0.006(3) C3B 0.046(4) 0.075(6) 0.056(5) -0.002(4) -0.006(4) 0.003(4) C4B 0.051(5) 0.045(4) 0.077(6) -0.007(4) -0.006(4) 0.007(4) C5B 0.052(5) 0.085(6) 0.087(6) -0.001(5) 0.002(5) -0.004(5) C6B 0.064(5) 0.050(5) 0.064(5) 0.013(4) -0.013(4) 0.003(4) C7B 0.115(9) 0.078(7) 0.158(10) 0.023(7) -0.064(8) -0.007(7) C8B 0.070(6) 0.074(6) 0.079(7) 0.028(6) -0.023(5) -0.017(5) C9B 0.091(8) 0.116(9) 0.097(7) 0.006(8) -0.007(7) -0.041(8) C10B 0.084(8) 0.119(10) 0.152(12) -0.017(10) -0.032(8) -0.010(7) C11B 0.100(10) 0.113(10) 0.175(16) 0.057(11) -0.076(10) -0.019(8) C12B 0.146(13) 0.169(15) 0.102(10) 0.053(11) -0.017(9) -0.011(12) C13B 0.087(8) 0.135(10) 0.110(9) 0.036(8) -0.020(7) 0.012(7) C14B 0.061(5) 0.067(5) 0.055(4) -0.003(4) 0.000(4) 0.004(4) C15B 0.053(5) 0.057(5) 0.065(5) -0.011(4) -0.002(4) 0.009(4) C16B 0.076(6) 0.109(8) 0.081(7) 0.012(6) 0.001(5) 0.007(6) C17B 0.107(9) 0.120(9) 0.122(9) 0.019(7) -0.032(8) 0.051(8) C18B 0.072(8) 0.108(9) 0.142(11) -0.025(8) -0.041(8) 0.046(6) C19B 0.078(8) 0.135(10) 0.110(9) -0.016(9) 0.002(7) 0.018(7) C20B 0.054(6) 0.086(6) 0.094(6) -0.005(5) 0.003(5) 0.018(5) C21B 0.067(6) 0.067(6) 0.053(5) -0.006(5) -0.002(4) 0.004(5) O4B 0.109(5) 0.114(6) 0.091(5) 0.031(4) -0.017(4) 0.024(4) C22B 0.174(11) 0.082(8) 0.061(6) -0.011(6) 0.024(7) -0.036(8) C23B 0.255(21) 0.078(9) 0.127(13) -0.026(9) 0.080(13) -0.024(11) C24B 0.226(18) 0.093(11) 0.142(13) 0.079(9) 0.076(12) 0.075(11) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag N1A C1A 1.348(10) . ? N1A C14A 1.453(10) . ? N1A C3A 1.477(10) . ? C1A O1A 1.216(10) . ? C1A C2A 1.520(11) . ? N2A C6A 1.359(10) . ? N2A C4A 1.441(9) . ? O2A C6A 1.208(9) . ? C2A C4A 1.537(10) . ? C2A C3A 1.541(10) . ? O3A C6A 1.329(9) . ? O3A C7A 1.446(9) . ? C3A C21A 1.477(10) . ? C4A C5A 1.554(10) . ? C7A C8A 1.489(13) . ? C8A C13A 1.32(2) . ? C8A C9A 1.387(15) . ? C9A C10A 1.38(2) . ? C10A C11A 1.29(3) . ? C11A C12A 1.36(3) . ? C12A C13A 1.40(2) . ? C14A C15A 1.503(11) . ? C15A C20A 1.351(11) . ? C15A C16A 1.364(11) . ? C16A C17A 1.412(12) . ? C17A C18A 1.318(14) . ? C18A C19A 1.339(15) . ? C19A C20A 1.387(14) . ? C21A C22A 1.334(11) . ? C21A O4A 1.349(9) . ? O4A C24A 1.368(10) . ? C22A C23A 1.439(12) . ? C23A C24A 1.282(13) . ? N1B C1B 1.353(10) . ? N1B C14B 1.443(10) . ? N1B C3B 1.457(9) . ? O1B C1B 1.210(9) . ? C1B C2B 1.546(11) . ? N2B C6B 1.307(10) . ? N2B C4B 1.487(9) . ? C2B C4B 1.524(10) . ? C2B C3B 1.551(10) . ? O2B C6B 1.206(8) . ? O3B C6B 1.350(8) . ? O3B C7B 1.438(10) . ? C3B C21B 1.471(11) . ? C4B C5B 1.501(10) . ? C7B C8B 1.503(12) . ? C8B C13B 1.345(14) . ? C8B C9B 1.363(14) . ? C9B C10B 1.39(2) . ? C10B C11B 1.39(2) . ? C11B C12B 1.29(2) . ? C12B C13B 1.37(2) . ? C14B C15B 1.514(11) . ? C15B C20B 1.352(11) . ? C15B C16B 1.368(11) . ? C16B C17B 1.386(13) . ? C17B C18B 1.38(2) . ? C18B C19B 1.304(15) . ? C19B C20B 1.377(14) . ? C21B C22B 1.307(12) . ? C21B O4B 1.343(10) . ? O4B C24B 1.401(14) . ? C22B C23B 1.36(2) . ? C23B C24B 1.32(2) . ? 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 C1A N1A C14A 130.8(8) . . ? C1A N1A C3A 95.1(7) . . ? C14A N1A C3A 132.6(7) . . ? O1A C1A N1A 130.6(9) . . ? O1A C1A C2A 137.4(8) . . ? N1A C1A C2A 92.1(7) . . ? C6A N2A C4A 121.4(6) . . ? C1A C2A C4A 118.9(6) . . ? C1A C2A C3A 85.9(6) . . ? C4A C2A C3A 118.2(6) . . ? C6A O3A C7A 112.8(6) . . ? N1A C3A C21A 116.6(7) . . ? N1A C3A C2A 86.5(5) . . ? C21A C3A C2A 119.8(7) . . ? N2A C4A C2A 112.5(6) . . ? N2A C4A C5A 108.9(6) . . ? C2A C4A C5A 110.3(6) . . ? O2A C6A O3A 125.4(8) . . ? O2A C6A N2A 123.3(8) . . ? O3A C6A N2A 111.4(7) . . ? O3A C7A C8A 109.4(8) . . ? C13A C8A C9A 119.2(11) . . ? C13A C8A C7A 120.3(13) . . ? C9A C8A C7A 120.6(14) . . ? C10A C9A C8A 118.9(15) . . ? C11A C10A C9A 117.9(20) . . ? C10A C11A C12A 127.5(24) . . ? C11A C12A C13A 112.6(21) . . ? C8A C13A C12A 123.6(16) . . ? N1A C14A C15A 112.8(6) . . ? C20A C15A C16A 117.9(8) . . ? C20A C15A C14A 123.3(7) . . ? C16A C15A C14A 118.8(8) . . ? C15A C16A C17A 120.7(9) . . ? C18A C17A C16A 119.1(10) . . ? C17A C18A C19A 121.5(11) . . ? C18A C19A C20A 119.8(10) . . ? C15A C20A C19A 121.0(9) . . ? C22A C21A O4A 111.0(7) . . ? C22A C21A C3A 131.4(8) . . ? O4A C21A C3A 117.6(7) . . ? C21A O4A C24A 106.2(7) . . ? C21A C22A C23A 104.2(8) . . ? C24A C23A C22A 108.4(9) . . ? C23A C24A O4A 110.2(9) . . ? C1B N1B C14B 130.4(7) . . ? C1B N1B C3B 95.8(6) . . ? C14B N1B C3B 133.4(7) . . ? O1B C1B N1B 132.7(8) . . ? O1B C1B C2B 135.6(8) . . ? N1B C1B C2B 91.6(7) . . ? C6B N2B C4B 122.3(6) . . ? C4B C2B C1B 119.0(6) . . ? C4B C2B C3B 120.8(6) . . ? C1B C2B C3B 84.7(6) . . ? C6B O3B C7B 113.7(7) . . ? N1B C3B C21B 117.2(7) . . ? N1B C3B C2B 87.6(5) . . ? C21B C3B C2B 120.5(6) . . ? N2B C4B C5B 109.4(6) . . ? N2B C4B C2B 112.3(6) . . ? C5B C4B C2B 113.3(7) . . ? O2B C6B N2B 125.9(7) . . ? O2B C6B O3B 122.6(8) . . ? N2B C6B O3B 111.5(7) . . ? O3B C7B C8B 109.0(8) . . ? C13B C8B C9B 118.7(10) . . ? C13B C8B C7B 118.3(11) . . ? C9B C8B C7B 122.9(11) . . ? C8B C9B C10B 121.6(12) . . ? C11B C10B C9B 115.4(13) . . ? C12B C11B C10B 123.1(13) . . ? C11B C12B C13B 120.1(15) . . ? C8B C13B C12B 120.9(13) . . ? N1B C14B C15B 112.7(6) . . ? C20B C15B C16B 119.5(9) . . ? C20B C15B C14B 118.8(8) . . ? C16B C15B C14B 121.8(8) . . ? C15B C16B C17B 119.8(10) . . ? C18B C17B C16B 118.8(10) . . ? C19B C18B C17B 120.8(10) . . ? C18B C19B C20B 121.1(11) . . ? C15B C20B C19B 120.0(9) . . ? C22B C21B O4B 111.1(9) . . ? C22B C21B C3B 131.7(9) . . ? O4B C21B C3B 117.0(8) . . ? C21B O4B C24B 103.5(10) . . ? C21B C22B C23B 109.0(12) . . ? C24B C23B C22B 106.3(13) . . ? C23B C24B O4B 110.1(13) . . ? 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 C14A N1A C1A O1A 8.1(14) . . . . ? C3A N1A C1A O1A 175.2(8) . . . . ? C14A N1A C1A C2A -172.4(8) . . . . ? C3A N1A C1A C2A -5.3(6) . . . . ? O1A C1A C2A C4A -55.4(13) . . . . ? N1A C1A C2A C4A 125.2(7) . . . . ? O1A C1A C2A C3A -175.5(10) . . . . ? N1A C1A C2A C3A 5.1(6) . . . . ? C1A N1A C3A C21A 127.0(7) . . . . ? C14A N1A C3A C21A -66.2(11) . . . . ? C1A N1A C3A C2A 5.3(6) . . . . ? C14A N1A C3A C2A 172.0(8) . . . . ? C1A C2A C3A N1A -4.7(5) . . . . ? C4A C2A C3A N1A -125.4(7) . . . . ? C1A C2A C3A C21A -123.5(8) . . . . ? C4A C2A C3A C21A 115.8(8) . . . . ? C6A N2A C4A C2A -99.7(8) . . . . ? C6A N2A C4A C5A 137.7(7) . . . . ? C1A C2A C4A N2A -59.5(9) . . . . ? C3A C2A C4A N2A 42.2(9) . . . . ? C1A C2A C4A C5A 62.3(9) . . . . ? C3A C2A C4A C5A 164.0(7) . . . . ? C7A O3A C6A O2A -0.3(14) . . . . ? C7A O3A C6A N2A 179.4(8) . . . . ? C4A N2A C6A O2A 3.9(13) . . . . ? C4A N2A C6A O3A -175.7(6) . . . . ? C6A O3A C7A C8A -171.4(10) . . . . ? O3A C7A C8A C13A -70.0(14) . . . . ? O3A C7A C8A C9A 111.9(12) . . . . ? C13A C8A C9A C10A -4.6(19) . . . . ? C7A C8A C9A C10A 173.6(12) . . . . ? C8A C9A C10A C11A 6.0(26) . . . . ? C9A C10A C11A C12A -6.1(37) . . . . ? C10A C11A C12A C13A 3.9(34) . . . . ? C9A C8A C13A C12A 2.7(18) . . . . ? C7A C8A C13A C12A -175.5(11) . . . . ? C11A C12A C13A C8A -2.0(23) . . . . ? C1A N1A C14A C15A 106.0(9) . . . . ? C3A N1A C14A C15A -56.4(11) . . . . ? N1A C14A C15A C20A 128.2(9) . . . . ? N1A C14A C15A C16A -53.5(10) . . . . ? C20A C15A C16A C17A -2.2(13) . . . . ? C14A C15A C16A C17A 179.5(9) . . . . ? C15A C16A C17A C18A 1.7(16) . . . . ? C16A C17A C18A C19A -0.8(18) . . . . ? C17A C18A C19A C20A 0.4(20) . . . . ? C16A C15A C20A C19A 1.8(15) . . . . ? C14A C15A C20A C19A -180.0(10) . . . . ? C18A C19A C20A C15A -0.9(19) . . . . ? N1A C3A C21A C22A 144.4(9) . . . . ? C2A C3A C21A C22A -113.6(10) . . . . ? N1A C3A C21A O4A -38.0(10) . . . . ? C2A C3A C21A O4A 64.0(10) . . . . ? C22A C21A O4A C24A 1.3(9) . . . . ? C3A C21A O4A C24A -176.7(7) . . . . ? O4A C21A C22A C23A -1.8(10) . . . . ? C3A C21A C22A C23A 175.9(9) . . . . ? C21A C22A C23A C24A 1.7(11) . . . . ? C22A C23A C24A O4A -1.0(11) . . . . ? C21A O4A C24A C23A -0.2(10) . . . . ? C14B N1B C1B O1B 0.4(15) . . . . ? C3B N1B C1B O1B 173.5(10) . . . . ? C14B N1B C1B C2B -177.5(7) . . . . ? C3B N1B C1B C2B -4.4(6) . . . . ? O1B C1B C2B C4B -51.2(12) . . . . ? N1B C1B C2B C4B 126.5(7) . . . . ? O1B C1B C2B C3B -173.6(10) . . . . ? N1B C1B C2B C3B 4.1(5) . . . . ? C1B N1B C3B C21B 127.6(7) . . . . ? C14B N1B C3B C21B -59.6(11) . . . . ? C1B N1B C3B C2B 4.3(6) . . . . ? C14B N1B C3B C2B 177.1(7) . . . . ? C4B C2B C3B N1B -124.6(6) . . . . ? C1B C2B C3B N1B -3.8(5) . . . . ? C4B C2B C3B C21B 115.0(8) . . . . ? C1B C2B C3B C21B -124.2(8) . . . . ? C6B N2B C4B C5B 139.7(8) . . . . ? C6B N2B C4B C2B -93.5(8) . . . . ? C1B C2B C4B N2B -62.6(8) . . . . ? C3B C2B C4B N2B 39.4(9) . . . . ? C1B C2B C4B C5B 62.1(9) . . . . ? C3B C2B C4B C5B 164.1(7) . . . . ? C4B N2B C6B O2B 5.1(13) . . . . ? C4B N2B C6B O3B -174.7(6) . . . . ? C7B O3B C6B O2B 0.9(13) . . . . ? C7B O3B C6B N2B -179.3(8) . . . . ? C6B O3B C7B C8B -171.6(8) . . . . ? O3B C7B C8B C13B 109.8(11) . . . . ? O3B C7B C8B C9B -73.4(13) . . . . ? C13B C8B C9B C10B -3.8(15) . . . . ? C7B C8B C9B C10B 179.4(9) . . . . ? C8B C9B C10B C11B 5.4(16) . . . . ? C9B C10B C11B C12B -3.5(20) . . . . ? C10B C11B C12B C13B 0.1(24) . . . . ? C9B C8B C13B C12B 0.1(17) . . . . ? C7B C8B C13B C12B 177.1(11) . . . . ? C11B C12B C13B C8B 1.7(21) . . . . ? C1B N1B C14B C15B 102.6(9) . . . . ? C3B N1B C14B C15B -67.9(10) . . . . ? N1B C14B C15B C20B 145.4(7) . . . . ? N1B C14B C15B C16B -33.0(11) . . . . ? C20B C15B C16B C17B 0.8(14) . . . . ? C14B C15B C16B C17B 179.2(9) . . . . ? C15B C16B C17B C18B 0.5(15) . . . . ? C16B C17B C18B C19B -2.3(17) . . . . ? C17B C18B C19B C20B 2.6(19) . . . . ? C16B C15B C20B C19B -0.6(14) . . . . ? C14B C15B C20B C19B -179.0(9) . . . . ? C18B C19B C20B C15B -1.2(17) . . . . ? N1B C3B C21B C22B 140.4(10) . . . . ? C2B C3B C21B C22B -115.3(11) . . . . ? N1B C3B C21B O4B -46.2(10) . . . . ? C2B C3B C21B O4B 58.2(10) . . . . ? C22B C21B O4B C24B 0.7(11) . . . . ? C3B C21B O4B C24B -174.1(9) . . . . ? O4B C21B C22B C23B -1.4(13) . . . . ? C3B C21B C22B C23B 172.4(10) . . . . ? C21B C22B C23B C24B 1.5(17) . . . . ? C22B C23B C24B O4B -1.1(19) . . . . ? C21B O4B C24B C23B 0.3(15) . . . . ? _refine_diff_density_max 0.132 _refine_diff_density_min -0.131 _refine_diff_density_rms 0.031 data_s561rm _database_code_CSD 165010 _publ_contact_author ' Joachim Podlech' _publ_contact_author_email joachim.podlech@po.uni-stuttgart.de loop_ _publ_author_name 'Michael R. Linder' 'Wolfgang U. Frey' 'Joachim Podlech' _journal_name_full 'Journal of the Chemical Society, Perkin Transactions 1' _journal_coden_Cambridge 207 _audit_creation_method SHELXL _chemical_name_systematic ; (3R,4S,1'S)-1-Benzyl-3-[1-(benzyloxycarbonylamino)ethyl]-4- (3-thienyl)-azetidin-2-one # The configuration has been determined relative to the configuration at 1' # which is given by the synthetic precursors ; _chemical_name_common ? _chemical_formula_moiety ? _chemical_formula_structural ? _chemical_formula_analytical ? _chemical_formula_sum 'C24 H24 N2 O3 S' _chemical_formula_weight 420.51 _chemical_melting_point '413 - 414 K' _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' '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 P2(1)2(1)2(1) 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 6.0550(10) _cell_length_b 17.352(3) _cell_length_c 20.987(3) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 2205.0(6) _cell_formula_units_Z 4 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 26 _cell_measurement_theta_min 10 _cell_measurement_theta_max 14 _exptl_crystal_description block _exptl_crystal_colour colourless _exptl_crystal_size_max 0.80 _exptl_crystal_size_mid 0.30 _exptl_crystal_size_min 0.25 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.267 _exptl_crystal_density_method ? _exptl_crystal_F_000 888 _exptl_absorpt_coefficient_mu 0.174 _exptl_absorpt_correction_type none _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 293(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device Nicolet P3 _diffrn_measurement_method Wyckoff - Scan _diffrn_standards_number 3 _diffrn_standards_interval_count 50 _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 2914 _diffrn_reflns_av_R_equivalents 0.0000 _diffrn_reflns_av_sigmaI/netI 0.0441 _diffrn_reflns_limit_h_min 0 _diffrn_reflns_limit_h_max 7 _diffrn_reflns_limit_k_min 0 _diffrn_reflns_limit_k_max 22 _diffrn_reflns_limit_l_min 0 _diffrn_reflns_limit_l_max 27 _diffrn_reflns_theta_min 1.52 _diffrn_reflns_theta_max 27.50 _reflns_number_total 2914 _reflns_number_observed 1912 _reflns_observed_criterion >2sigma(I) _computing_data_collection Siemens P3/V Data Collection System _computing_cell_refinement Siemens P3/V Data Collection System _computing_data_reduction SHELXTL plus - XDISK _computing_structure_solution 'SHELXS-86 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-93 (Sheldrick, 1993)' _computing_molecular_graphics SHELXTL - XP _computing_publication_material ? _refine_special_details ; Refinement on F^2^ for ALL reflections except for 323 with very negative F^2^ or flagged by the user for potential systematic errors. Weighted R-factors wR and all goodnesses 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 observed criterion of F^2^ > 2sigma(F^2^) is used only for calculating _R_factor_obs 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 w=1/[\s^2^(Fo^2^)+(0.0378P)^2^+0.4336P] 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 ? _refine_ls_extinction_method SHELXL _refine_ls_extinction_coef 0.0131(12) _refine_ls_extinction_expression 'Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^' _refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _refine_ls_abs_structure_Flack 0.00(23) _refine_ls_number_reflns 2591 _refine_ls_number_parameters 309 _refine_ls_number_restraints 148 _refine_ls_R_factor_all 0.0978 _refine_ls_R_factor_obs 0.0520 _refine_ls_wR_factor_all 0.1282 _refine_ls_wR_factor_obs 0.1001 _refine_ls_goodness_of_fit_all 1.097 _refine_ls_goodness_of_fit_obs 1.190 _refine_ls_restrained_S_all 1.184 _refine_ls_restrained_S_obs 1.165 _refine_ls_shift/esd_max -0.001 _refine_ls_shift/esd_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_thermal_displace_type _atom_site_occupancy _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_group O1 O -0.3807(4) 0.9812(2) -0.17916(13) 0.0645(8) Uani 1 d . . N1 N -0.0980(5) 0.89786(15) -0.14948(13) 0.0473(7) Uani 1 d . . C1 C -0.2046(6) 0.9652(2) -0.1545(2) 0.0474(8) Uani 1 d . . O2 O 0.2177(5) 1.1623(2) -0.04367(14) 0.0705(8) Uani 1 d . . N2 N 0.3102(5) 1.08839(15) -0.12864(13) 0.0456(7) Uani 1 d . . H2 H 0.4212(5) 1.07055(15) -0.14952(13) 0.055 Uiso 1 calc R . C2 C -0.0207(5) 1.0088(2) -0.1200(2) 0.0422(8) Uani 1 d . . H2A H -0.0673(5) 1.0240(2) -0.0770(2) 0.051 Uiso 1 calc R . O3 O 0.5660(4) 1.11880(14) -0.05905(12) 0.0546(7) Uani 1 d . . C3 C 0.1011(6) 0.9297(2) -0.1188(2) 0.0409(7) Uani 1 d . . H3 H 0.2272(6) 0.9294(2) -0.1481(2) 0.049 Uiso 1 calc R . C4 C 0.0916(6) 1.0758(2) -0.1545(2) 0.0484(9) Uani 1 d . . H4 H 0.0037(6) 1.1224(2) -0.1475(2) 0.058 Uiso 1 calc R . C5 C 0.1115(7) 1.0627(2) -0.2259(2) 0.0688(12) Uani 1 d . . H5A H 0.1828(7) 1.1063(2) -0.2452(2) 0.103 Uiso 1 calc R . H5B H -0.0331(7) 1.0565(2) -0.2440(2) 0.103 Uiso 1 calc R . H5C H 0.1973(7) 1.0172(2) -0.2337(2) 0.103 Uiso 1 calc R . C6 C 0.3502(6) 1.1260(2) -0.0744(2) 0.0454(8) Uani 1 d . . C7 C 0.6463(8) 1.1577(2) -0.0033(2) 0.0621(11) Uani 1 d . . H7A H 0.5345(8) 1.1932(2) 0.0120(2) 0.074 Uiso 1 calc R . H7B H 0.7766(8) 1.1874(2) -0.0143(2) 0.074 Uiso 1 calc R . C8 C 0.7027(7) 1.1018(2) 0.0485(2) 0.0532(9) Uani 1 d . . C9 C 0.8981(8) 1.1096(3) 0.0810(2) 0.0714(12) Uani 1 d . . H9 H 0.9962(8) 1.1483(3) 0.0693(2) 0.086 Uiso 1 calc R . C10 C 0.9522(8) 1.0607(3) 0.1310(2) 0.0839(14) Uani 1 d . . H10 H 1.0850(8) 1.0668(3) 0.1526(2) 0.101 Uiso 1 calc R . C11 C 0.8100(9) 1.0038(3) 0.1482(2) 0.0813(14) Uani 1 d . . H11 H 0.8447(9) 0.9712(3) 0.1819(2) 0.098 Uiso 1 calc R . C12 C 0.6173(10) 0.9946(3) 0.1161(2) 0.0841(15) Uani 1 d . . H12 H 0.5210(10) 0.9553(3) 0.1277(2) 0.101 Uiso 1 calc R . C13 C 0.5629(7) 1.0433(3) 0.0663(2) 0.0720(12) Uani 1 d . . H13 H 0.4303(7) 1.0364(3) 0.0447(2) 0.086 Uiso 1 calc R . C14 C -0.1534(7) 0.8209(2) -0.1717(2) 0.0632(11) Uani 1 d . . H14A H -0.2966(7) 0.8221(2) -0.1924(2) 0.076 Uiso 1 calc R . H14B H -0.1640(7) 0.7865(2) -0.1354(2) 0.076 Uiso 1 calc R . C15 C 0.0152(6) 0.7900(2) -0.2175(2) 0.0480(9) Uani 1 d . . C16 C 0.1830(8) 0.7436(2) -0.1974(2) 0.0693(12) Uani 1 d . . H16 H 0.1904(8) 0.7295(2) -0.1547(2) 0.083 Uiso 1 calc R . C17 C 0.3417(9) 0.7172(3) -0.2389(3) 0.0858(15) Uani 1 d . . H17 H 0.4563(9) 0.6863(3) -0.2241(3) 0.103 Uiso 1 calc R . C18 C 0.3303(11) 0.7364(3) -0.3019(3) 0.094(2) Uani 1 d . . H18 H 0.4370(11) 0.7186(3) -0.3302(3) 0.113 Uiso 1 calc R . C19 C 0.1634(11) 0.7814(3) -0.3231(2) 0.091(2) Uani 1 d . . H19 H 0.1560(11) 0.7946(3) -0.3660(2) 0.110 Uiso 1 calc R . C20 C 0.0032(9) 0.8079(2) -0.2814(2) 0.0708(12) Uani 1 d . . H20 H -0.1127(9) 0.8380(2) -0.2965(2) 0.085 Uiso 1 calc R . C21 C 0.1613(6) 0.8948(2) -0.0558(2) 0.0480(8) Uani 1 d D . S1 S 0.1549(5) 0.8522(2) 0.0607(2) 0.0787(9) Uani 0.617(6) d PDU 1 C24 C 0.3723(23) 0.8285(12) 0.0148(6) 0.090(6) Uani 0.617(6) d PDU 1 H24 H 0.4880(23) 0.7979(12) 0.0293(6) 0.108 Uiso 0.617(6) calc PR 1 C22 C 0.0412(17) 0.8951(11) -0.0032(3) 0.092(6) Uani 0.617(6) d PDU 1 H22 H -0.0980(17) 0.9176(11) -0.0016(3) 0.111 Uiso 0.617(6) calc PR 1 C23 C 0.3648(16) 0.8570(9) -0.0435(5) 0.064(4) Uani 0.617(6) d PDU 1 H23 H 0.4790(16) 0.8528(9) -0.0730(5) 0.077 Uiso 0.617(6) calc PR 1 C24' C 0.1240(22) 0.8576(14) 0.0441(8) 0.109(10) Uani 0.383(6) d PDU 2 H24' H 0.0529(22) 0.8476(14) 0.0825(8) 0.131 Uiso 0.383(6) calc PR 2 S1' S 0.3737(14) 0.8198(6) 0.0282(4) 0.087(2) Uani 0.383(6) d PDU 2 C23' C 0.0318(21) 0.9019(11) 0.0004(4) 0.041(4) Uani 0.383(6) d PDU 2 H23' H -0.0939(21) 0.9321(11) 0.0054(4) 0.049 Uiso 0.383(6) calc PR 2 C22' C 0.3288(34) 0.8470(15) -0.0477(5) 0.063(6) Uani 0.383(6) d PDU 2 H22' H 0.4154(34) 0.8297(15) -0.0813(5) 0.075 Uiso 0.383(6) calc PR 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 O1 0.0363(14) 0.075(2) 0.082(2) -0.0219(15) -0.0044(15) 0.0078(14) N1 0.043(2) 0.0434(15) 0.056(2) -0.0094(13) 0.004(2) 0.0014(14) C1 0.034(2) 0.054(2) 0.054(2) -0.012(2) 0.005(2) -0.001(2) O2 0.063(2) 0.069(2) 0.080(2) -0.026(2) 0.008(2) 0.012(2) N2 0.039(2) 0.046(2) 0.052(2) -0.0087(13) -0.0006(14) 0.0027(14) C2 0.035(2) 0.045(2) 0.047(2) -0.0077(15) 0.001(2) 0.006(2) O3 0.0509(15) 0.0621(15) 0.0509(14) -0.0124(12) -0.0068(13) 0.0000(13) C3 0.034(2) 0.042(2) 0.047(2) -0.0026(14) 0.006(2) 0.0010(14) C4 0.041(2) 0.045(2) 0.059(2) -0.002(2) -0.011(2) 0.007(2) C5 0.070(3) 0.080(3) 0.056(2) 0.017(2) -0.015(2) -0.017(3) C6 0.047(2) 0.038(2) 0.051(2) 0.0009(15) -0.002(2) -0.002(2) C7 0.071(3) 0.058(2) 0.058(2) -0.012(2) -0.015(2) -0.011(2) C8 0.058(2) 0.055(2) 0.047(2) -0.012(2) 0.002(2) -0.002(2) C9 0.067(3) 0.084(3) 0.063(3) 0.006(2) -0.006(2) -0.012(3) C10 0.068(3) 0.116(4) 0.067(3) 0.008(3) -0.007(3) -0.002(3) C11 0.089(4) 0.093(3) 0.061(3) 0.015(2) 0.006(3) 0.008(3) C12 0.100(4) 0.087(3) 0.065(3) 0.010(2) 0.002(3) -0.024(3) C13 0.067(3) 0.093(3) 0.057(2) -0.001(2) -0.006(2) -0.022(3) C14 0.067(3) 0.046(2) 0.077(3) -0.015(2) 0.016(2) -0.015(2) C15 0.055(2) 0.0310(15) 0.058(2) -0.011(2) 0.006(2) -0.004(2) C16 0.075(3) 0.058(2) 0.074(3) -0.008(2) -0.005(3) 0.004(2) C17 0.067(3) 0.068(3) 0.123(4) -0.027(3) -0.005(3) 0.017(3) C18 0.092(4) 0.078(3) 0.113(4) -0.046(3) 0.031(4) -0.004(3) C19 0.117(5) 0.095(3) 0.062(3) -0.016(3) 0.025(3) -0.006(4) C20 0.082(3) 0.063(2) 0.068(3) -0.001(2) -0.001(3) 0.007(3) C21 0.052(2) 0.041(2) 0.051(2) -0.001(2) 0.010(2) 0.001(2) S1 0.104(2) 0.0785(15) 0.0538(13) 0.0155(10) 0.0028(14) -0.0024(14) C24 0.090(8) 0.092(9) 0.088(10) 0.021(6) -0.009(6) 0.024(6) C22 0.089(8) 0.091(8) 0.096(8) 0.012(6) -0.001(7) 0.017(7) C23 0.056(6) 0.068(6) 0.069(6) 0.006(4) 0.002(4) 0.015(6) C24' 0.126(13) 0.114(12) 0.088(13) 0.011(8) 0.002(8) -0.005(8) S1' 0.117(4) 0.080(3) 0.064(3) 0.024(2) -0.010(3) 0.018(3) C23' 0.050(7) 0.042(6) 0.031(6) 0.003(5) 0.023(6) 0.006(5) C22' 0.062(8) 0.074(9) 0.051(8) -0.002(6) -0.005(6) 0.002(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 O1 C1 1.218(4) . ? N1 C1 1.339(4) . ? N1 C14 1.454(4) . ? N1 C3 1.474(4) . ? C1 C2 1.528(5) . ? O2 C6 1.206(4) . ? N2 C6 1.335(4) . ? N2 C4 1.448(4) . ? N2 H2 0.86 . ? C2 C4 1.529(4) . ? C2 C3 1.559(4) . ? C2 H2A 0.98 . ? O3 C6 1.352(4) . ? O3 C7 1.436(4) . ? C3 C21 1.500(5) . ? C3 H3 0.98 . ? C4 C5 1.520(5) . ? C4 H4 0.98 . ? C5 H5A 0.96 . ? C5 H5B 0.96 . ? C5 H5C 0.96 . ? C7 C8 1.497(5) . ? C7 H7A 0.97 . ? C7 H7B 0.97 . ? C8 C9 1.372(5) . ? C8 C13 1.373(5) . ? C9 C10 1.389(6) . ? C9 H9 0.93 . ? C10 C11 1.358(6) . ? C10 H10 0.93 . ? C11 C12 1.356(6) . ? C11 H11 0.93 . ? C12 C13 1.384(6) . ? C12 H12 0.93 . ? C13 H13 0.93 . ? C14 C15 1.501(5) . ? C14 H14A 0.97 . ? C14 H14B 0.97 . ? C15 C16 1.363(5) . ? C15 C20 1.379(5) . ? C16 C17 1.376(6) . ? C16 H16 0.93 . ? C17 C18 1.365(7) . ? C17 H17 0.93 . ? C18 C19 1.352(7) . ? C18 H18 0.93 . ? C19 C20 1.386(6) . ? C19 H19 0.93 . ? C20 H20 0.93 . ? C21 C22 1.3210(11) . ? C21 C22' 1.3215(15) . ? C21 C23 1.4201(11) . ? C21 C23' 1.4203(15) . ? S1 C22 1.6812(11) . ? S1 C24 1.6818(15) . ? C24 C23 1.3217(15) . ? C24 H24 0.93 . ? C22 H22 0.93 . ? C23 H23 0.93 . ? C24' C23' 1.3216(15) . ? C24' S1' 1.6817(15) . ? C24' H24' 0.93 . ? S1' C22' 1.6818(15) . ? C23' H23' 0.93 . ? C22' H22' 0.93 . ? 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 C1 N1 C14 131.7(3) . . ? C1 N1 C3 95.8(2) . . ? C14 N1 C3 132.3(3) . . ? O1 C1 N1 130.9(3) . . ? O1 C1 C2 136.6(3) . . ? N1 C1 C2 92.5(3) . . ? C6 N2 C4 124.0(3) . . ? C6 N2 H2 118.0(2) . . ? C4 N2 H2 118.0(2) . . ? C1 C2 C4 118.4(3) . . ? C1 C2 C3 85.2(2) . . ? C4 C2 C3 117.8(3) . . ? C1 C2 H2A 111.1(2) . . ? C4 C2 H2A 111.1(2) . . ? C3 C2 H2A 111.1(2) . . ? C6 O3 C7 118.6(3) . . ? N1 C3 C21 115.7(3) . . ? N1 C3 C2 86.3(2) . . ? C21 C3 C2 118.9(3) . . ? N1 C3 H3 111.3(2) . . ? C21 C3 H3 111.3(2) . . ? C2 C3 H3 111.3(2) . . ? N2 C4 C5 108.7(3) . . ? N2 C4 C2 110.1(3) . . ? C5 C4 C2 112.9(3) . . ? N2 C4 H4 108.4(2) . . ? C5 C4 H4 108.4(2) . . ? C2 C4 H4 108.4(2) . . ? C4 C5 H5A 109.5(2) . . ? C4 C5 H5B 109.5(2) . . ? H5A C5 H5B 109.5 . . ? C4 C5 H5C 109.5(2) . . ? H5A C5 H5C 109.5 . . ? H5B C5 H5C 109.5 . . ? O2 C6 N2 126.2(4) . . ? O2 C6 O3 124.3(3) . . ? N2 C6 O3 109.5(3) . . ? O3 C7 C8 111.4(3) . . ? O3 C7 H7A 109.3(2) . . ? C8 C7 H7A 109.3(2) . . ? O3 C7 H7B 109.3(2) . . ? C8 C7 H7B 109.3(2) . . ? H7A C7 H7B 108.0 . . ? C9 C8 C13 118.0(4) . . ? C9 C8 C7 119.6(4) . . ? C13 C8 C7 122.4(4) . . ? C8 C9 C10 121.2(4) . . ? C8 C9 H9 119.4(3) . . ? C10 C9 H9 119.4(3) . . ? C11 C10 C9 119.7(4) . . ? C11 C10 H10 120.2(3) . . ? C9 C10 H10 120.2(3) . . ? C12 C11 C10 119.9(5) . . ? C12 C11 H11 120.0(3) . . ? C10 C11 H11 120.0(3) . . ? C11 C12 C13 120.5(5) . . ? C11 C12 H12 119.7(3) . . ? C13 C12 H12 119.7(3) . . ? C8 C13 C12 120.7(4) . . ? C8 C13 H13 119.7(2) . . ? C12 C13 H13 119.7(3) . . ? N1 C14 C15 112.1(3) . . ? N1 C14 H14A 109.2(2) . . ? C15 C14 H14A 109.2(2) . . ? N1 C14 H14B 109.2(2) . . ? C15 C14 H14B 109.2(2) . . ? H14A C14 H14B 107.9 . . ? C16 C15 C20 118.2(4) . . ? C16 C15 C14 121.3(4) . . ? C20 C15 C14 120.5(4) . . ? C15 C16 C17 121.5(4) . . ? C15 C16 H16 119.3(2) . . ? C17 C16 H16 119.3(3) . . ? C18 C17 C16 119.8(5) . . ? C18 C17 H17 120.1(4) . . ? C16 C17 H17 120.1(3) . . ? C19 C18 C17 119.8(5) . . ? C19 C18 H18 120.1(3) . . ? C17 C18 H18 120.1(3) . . ? C18 C19 C20 120.5(5) . . ? C18 C19 H19 119.8(3) . . ? C20 C19 H19 119.8(3) . . ? C15 C20 C19 120.2(4) . . ? C15 C20 H20 119.9(3) . . ? C19 C20 H20 119.9(3) . . ? C22 C21 C23 109.2(5) . . ? C22' C21 C23' 111.8(7) . . ? C22 C21 C3 127.0(3) . . ? C22' C21 C3 123.6(5) . . ? C23 C21 C3 123.8(5) . . ? C23' C21 C3 124.3(5) . . ? C22 S1 C24 88.4(5) . . ? C23 C24 S1 114.3(8) . . ? C23 C24 H24 122.8(4) . . ? S1 C24 H24 122.8(4) . . ? C21 C22 S1 116.0(4) . . ? C21 C22 H22 122.0(2) . . ? S1 C22 H22 122.0(2) . . ? C24 C23 C21 111.7(9) . . ? C24 C23 H23 124.1(5) . . ? C21 C23 H23 124.1(4) . . ? C23' C24' S1' 117.9(10) . . ? C23' C24' H24' 121.1(5) . . ? S1' C24' H24' 121.1(5) . . ? C22' S1' C24' 86.2(8) . . ? C24' C23' C21 107.0(9) . . ? C24' C23' H23' 126.5(5) . . ? C21 C23' H23' 126.5(5) . . ? C21 C22' S1' 114.9(7) . . ? C21 C22' H22' 122.5(4) . . ? S1' C22' H22' 122.5(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 C14 N1 C1 O1 0.3(7) . . . . ? C3 N1 C1 O1 175.8(4) . . . . ? C14 N1 C1 C2 -178.6(4) . . . . ? C3 N1 C1 C2 -3.0(3) . . . . ? O1 C1 C2 C4 -56.8(6) . . . . ? N1 C1 C2 C4 121.9(3) . . . . ? O1 C1 C2 C3 -175.9(5) . . . . ? N1 C1 C2 C3 2.9(3) . . . . ? C1 N1 C3 C21 123.4(3) . . . . ? C14 N1 C3 C21 -61.1(5) . . . . ? C1 N1 C3 C2 3.0(3) . . . . ? C14 N1 C3 C2 178.5(4) . . . . ? C1 C2 C3 N1 -2.6(2) . . . . ? C4 C2 C3 N1 -122.3(3) . . . . ? C1 C2 C3 C21 -120.0(3) . . . . ? C4 C2 C3 C21 120.4(3) . . . . ? C6 N2 C4 C5 156.6(3) . . . . ? C6 N2 C4 C2 -79.3(4) . . . . ? C1 C2 C4 N2 -156.1(3) . . . . ? C3 C2 C4 N2 -55.9(4) . . . . ? C1 C2 C4 C5 -34.5(4) . . . . ? C3 C2 C4 C5 65.7(4) . . . . ? C4 N2 C6 O2 -9.6(5) . . . . ? C4 N2 C6 O3 171.7(3) . . . . ? C7 O3 C6 O2 -1.2(5) . . . . ? C7 O3 C6 N2 177.6(3) . . . . ? C6 O3 C7 C8 109.9(4) . . . . ? O3 C7 C8 C9 134.0(4) . . . . ? O3 C7 C8 C13 -47.6(5) . . . . ? C13 C8 C9 C10 -1.0(6) . . . . ? C7 C8 C9 C10 177.5(4) . . . . ? C8 C9 C10 C11 0.3(7) . . . . ? C9 C10 C11 C12 0.6(8) . . . . ? C10 C11 C12 C13 -0.7(8) . . . . ? C9 C8 C13 C12 0.9(6) . . . . ? C7 C8 C13 C12 -177.5(4) . . . . ? C11 C12 C13 C8 0.0(7) . . . . ? C1 N1 C14 C15 119.3(4) . . . . ? C3 N1 C14 C15 -54.7(5) . . . . ? N1 C14 C15 C16 95.6(4) . . . . ? N1 C14 C15 C20 -84.7(4) . . . . ? C20 C15 C16 C17 2.3(6) . . . . ? C14 C15 C16 C17 -178.0(4) . . . . ? C15 C16 C17 C18 -1.2(7) . . . . ? C16 C17 C18 C19 0.1(8) . . . . ? C17 C18 C19 C20 -0.2(8) . . . . ? C16 C15 C20 C19 -2.3(6) . . . . ? C14 C15 C20 C19 177.9(4) . . . . ? C18 C19 C20 C15 1.4(7) . . . . ? N1 C3 C21 C22 -61.3(12) . . . . ? C2 C3 C21 C22 39.3(13) . . . . ? N1 C3 C21 C22' 106.2(18) . . . . ? C2 C3 C21 C22' -153.2(18) . . . . ? N1 C3 C21 C23 120.0(9) . . . . ? C2 C3 C21 C23 -139.4(9) . . . . ? N1 C3 C21 C23' -66.2(12) . . . . ? C2 C3 C21 C23' 34.4(12) . . . . ? C22 S1 C24 C23 4.9(19) . . . . ? C22' C21 C22 S1 11.7(21) . . . . ? C23 C21 C22 S1 -0.4(18) . . . . ? C23' C21 C22 S1 -122.4(140) . . . . ? C3 C21 C22 S1 -179.2(6) . . . . ? C24 S1 C22 C21 -2.4(16) . . . . ? S1 C24 C23 C21 -6.1(24) . . . . ? C22 C21 C23 C24 4.1(21) . . . . ? C22' C21 C23 C24 -84.6(48) . . . . ? C23' C21 C23 C24 8.4(21) . . . . ? C3 C21 C23 C24 -177.1(13) . . . . ? C23' C24' S1' C22' -13.4(25) . . . . ? S1' C24' C23' C21 10.0(27) . . . . ? C22 C21 C23' C24' 47.5(119) . . . . ? C22' C21 C23' C24' 0.4(25) . . . . ? C23 C21 C23' C24' -12.0(22) . . . . ? C3 C21 C23' C24' 173.6(14) . . . . ? C22 C21 C22' S1' -14.1(26) . . . . ? C23 C21 C22' S1' 81.2(35) . . . . ? C23' C21 C22' S1' -10.4(27) . . . . ? C3 C21 C22' S1' 176.3(11) . . . . ? C24' S1' C22' C21 13.0(24) . . . . ? _refine_diff_density_max 0.157 _refine_diff_density_min -0.150 _refine_diff_density_rms 0.037 data_s624rm _database_code_CSD 165011 _publ_contact_author ' Joachim Podlech' _publ_contact_author_email joachim.podlech@po.uni-stuttgart.de loop_ _publ_author_name 'Michael R. Linder' 'Wolfgang U. Frey' 'Joachim Podlech' _journal_name_full 'Journal of the Chemical Society, Perkin Transactions 1' _journal_coden_Cambridge 207 _audit_creation_method SHELXL _chemical_name_systematic ; (3R,4S,1'S)-3-[1-(Benzyloxycarbonylamino)ethyl]-1-tert-butyl-4- mesityl-azetidin-2-one # The configuration has been determined relative to the configuration at 1' # which is given by the synthetic precursors ; _chemical_name_common ? _chemical_formula_moiety ? _chemical_formula_structural ? _chemical_formula_analytical ? _chemical_formula_sum 'C26 H34 N2 O3' _chemical_formula_weight 422.55 _chemical_melting_point '395 - 396 K' _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' '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' _symmetry_cell_setting orthorhombic _symmetry_space_group_name_H-M P2(1)2(1)2(1) 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 9.742(2) _cell_length_b 15.886(3) _cell_length_c 32.683(5) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 5058.0(17) _cell_formula_units_Z 8 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 25 _cell_measurement_theta_min 8 _cell_measurement_theta_max 12 _exptl_crystal_description plates _exptl_crystal_colour colourless _exptl_crystal_size_max 1.20 _exptl_crystal_size_mid 0.20 _exptl_crystal_size_min 0.07 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.110 _exptl_crystal_density_method ? _exptl_crystal_F_000 1824 _exptl_absorpt_coefficient_mu 0.072 _exptl_absorpt_correction_type none _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 293(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device Nicolet P3 _diffrn_measurement_method Wyckoff - Scan _diffrn_standards_number 3 _diffrn_standards_interval_count 50 _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 3739 _diffrn_reflns_av_R_equivalents 0.0000 _diffrn_reflns_av_sigmaI/netI 0.0838 _diffrn_reflns_limit_h_min 0 _diffrn_reflns_limit_h_max 11 _diffrn_reflns_limit_k_min 0 _diffrn_reflns_limit_k_max 18 _diffrn_reflns_limit_l_min 0 _diffrn_reflns_limit_l_max 38 _diffrn_reflns_theta_min 1.25 _diffrn_reflns_theta_max 22.50 _reflns_number_total 3739 _reflns_number_observed 2102 _reflns_observed_criterion >2sigma(I) _computing_data_collection Siemens P3/PC Data Collection System _computing_cell_refinement Siemens P3/PC Data Collection System _computing_data_reduction SHELXTL plus - XDISK _computing_structure_solution 'SHELXS-86 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-93 (Sheldrick, 1993)' _computing_molecular_graphics SHELXTL - XP _computing_publication_material ? _refine_special_details ; Refinement on F^2^ for ALL reflections except for 463 with very negative F^2^ or flagged by the user for potential systematic errors. Weighted R-factors wR and all goodnesses 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 observed criterion of F^2^ > 2sigma(F^2^) is used only for calculating _R_factor_obs 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 w=1/[\s^2^(Fo^2^)+(0.0622P)^2^+5.9079P] 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 ? _refine_ls_extinction_method SHELXL _refine_ls_extinction_coef 0.0012(5) _refine_ls_extinction_expression 'Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^' _refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _refine_ls_abs_structure_Flack 4.37(530) _refine_ls_number_reflns 3276 _refine_ls_number_parameters 560 _refine_ls_number_restraints 6 _refine_ls_R_factor_all 0.1786 _refine_ls_R_factor_obs 0.0970 _refine_ls_wR_factor_all 0.2476 _refine_ls_wR_factor_obs 0.1879 _refine_ls_goodness_of_fit_all 1.150 _refine_ls_goodness_of_fit_obs 1.338 _refine_ls_restrained_S_all 1.247 _refine_ls_restrained_S_obs 1.348 _refine_ls_shift/esd_max -0.003 _refine_ls_shift/esd_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_thermal_displace_type _atom_site_occupancy _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_group N1A N 0.3937(10) 0.5473(6) 0.9991(3) 0.066(3) Uani 1 d . . O1A O 0.5904(9) 0.4716(6) 0.9811(3) 0.086(3) Uani 1 d . . C1A C 0.4656(13) 0.4841(9) 0.9826(4) 0.073(4) Uani 1 d . . N2A N 0.3940(9) 0.5093(5) 0.9002(3) 0.054(2) Uani 1 d . . H2A H 0.4819(9) 0.5135(5) 0.8989(3) 0.065 Uiso 1 calc R . O2A O 0.1940(9) 0.5758(6) 0.8841(3) 0.086(3) Uani 1 d . . C2A C 0.3415(11) 0.4414(7) 0.9656(3) 0.057(3) Uani 1 d . . H2A1 H 0.3235(11) 0.3873(7) 0.9789(3) 0.069 Uiso 1 calc R . O3A O 0.4008(9) 0.6314(5) 0.8694(2) 0.074(2) Uani 1 d . . C3A C 0.2590(11) 0.5142(7) 0.9853(3) 0.056(3) Uani 1 d . . H3A H 0.2226(11) 0.5507(7) 0.9637(3) 0.067 Uiso 1 calc R . C4A C 0.3352(12) 0.4348(8) 0.9187(3) 0.066(3) Uani 1 d . . H4A H 0.2391(12) 0.4296(8) 0.9102(3) 0.079 Uiso 1 calc R . C5A C 0.4155(16) 0.3571(8) 0.9039(4) 0.103(5) Uani 1 d . . H5A1 H 0.4107(16) 0.3538(8) 0.8746(4) 0.154 Uiso 1 calc R . H5A2 H 0.3762(16) 0.3072(8) 0.9156(4) 0.154 Uiso 1 calc R . H5A3 H 0.5097(16) 0.3618(8) 0.9122(4) 0.154 Uiso 1 calc R . C6A C 0.3179(13) 0.5713(8) 0.8852(4) 0.061(3) Uani 1 d . . C7A C 0.3290(15) 0.7025(9) 0.8506(5) 0.105(5) Uani 1 d . . H7A1 H 0.2598(15) 0.7245(9) 0.8690(5) 0.125 Uiso 1 calc R . H7A2 H 0.2847(15) 0.6851(9) 0.8254(5) 0.125 Uiso 1 calc R . C8A C 0.4344(14) 0.7670(9) 0.8421(4) 0.074(4) Uani 1 d . . C9A C 0.4769(19) 0.7742(9) 0.8041(6) 0.108(6) Uani 1 d . . H9A H 0.4440(19) 0.7353(9) 0.7852(6) 0.130 Uiso 1 calc R . C10A C 0.5668(33) 0.8353(18) 0.7899(7) 0.178(16) Uani 1 d . . H10A H 0.5807(33) 0.8464(18) 0.7623(7) 0.214 Uiso 1 calc R . C11A C 0.6316(24) 0.8765(19) 0.8198(11) 0.178(17) Uani 1 d . . H11A H 0.7108(24) 0.9059(19) 0.8129(11) 0.213 Uiso 1 calc R . C12A C 0.5920(24) 0.8788(15) 0.8589(9) 0.170(12) Uani 1 d . . H12A H 0.6275(24) 0.9179(15) 0.8772(9) 0.204 Uiso 1 calc R . C13A C 0.4951(21) 0.8198(13) 0.8706(6) 0.131(7) Uani 1 d . . H13A H 0.4705(21) 0.8155(13) 0.8980(6) 0.158 Uiso 1 calc R . C14A C 0.1472(11) 0.4977(7) 1.0167(3) 0.055(3) Uani 1 d . . C15A C 0.1692(13) 0.4516(9) 1.0521(4) 0.078(4) Uani 1 d . . C16A C 0.0620(17) 0.4414(10) 1.0801(5) 0.102(5) Uani 1 d . . H16A H 0.0782(17) 0.4113(10) 1.1040(5) 0.123 Uiso 1 calc R . C17A C -0.0673(17) 0.4743(12) 1.0734(5) 0.107(6) Uani 1 d . . C18A C -0.0903(14) 0.5147(10) 1.0371(4) 0.089(5) Uani 1 d . . H18A H -0.1786(14) 0.5329(10) 1.0310(4) 0.107 Uiso 1 calc R . C19A C 0.0159(12) 0.5297(7) 1.0087(4) 0.059(3) Uani 1 d . . C20A C 0.3061(16) 0.4126(11) 1.0631(5) 0.133(7) Uani 1 d . . H20A H 0.2983(16) 0.3837(11) 1.0888(5) 0.200 Uiso 1 calc R . H20B H 0.3744(16) 0.4559(11) 1.0653(5) 0.200 Uiso 1 calc R . H20C H 0.3325(16) 0.3733(11) 1.0422(5) 0.200 Uiso 1 calc R . C21A C -0.1829(17) 0.4671(14) 1.1053(5) 0.161(9) Uani 1 d . . H21A H -0.1497(17) 0.4371(14) 1.1288(5) 0.241 Uiso 1 calc R . H21B H -0.2592(17) 0.4373(14) 1.0937(5) 0.241 Uiso 1 calc R . H21C H -0.2118(17) 0.5224(14) 1.1134(5) 0.241 Uiso 1 calc R . C22A C -0.0199(12) 0.5764(8) 0.9694(4) 0.087(4) Uani 1 d . . H22A H -0.1146(12) 0.5930(8) 0.9701(4) 0.131 Uiso 1 calc R . H22B H -0.0045(12) 0.5401(8) 0.9464(4) 0.131 Uiso 1 calc R . H22C H 0.0369(12) 0.6256(8) 0.9670(4) 0.131 Uiso 1 calc R . C23A C 0.4305(18) 0.6294(11) 1.0144(5) 0.103(5) Uani 1 d . . C24A C 0.4918(27) 0.6742(13) 0.9797(7) 0.211(10) Uani 1 d U . H24A H 0.5687(27) 0.6428(13) 0.9695(7) 0.316 Uiso 1 calc R . H24B H 0.5221(27) 0.7288(13) 0.9885(7) 0.316 Uiso 1 calc R . H24C H 0.4247(27) 0.6804(13) 0.9584(7) 0.316 Uiso 1 calc R . C25A C 0.3118(17) 0.6753(10) 1.0312(6) 0.143(8) Uani 1 d . . H25A H 0.2741(17) 0.6444(10) 1.0538(6) 0.214 Uiso 1 calc R . H25B H 0.2432(17) 0.6815(10) 1.0103(6) 0.214 Uiso 1 calc R . H25C H 0.3406(17) 0.7299(10) 1.0404(6) 0.214 Uiso 1 calc R . C26A C 0.5405(24) 0.6264(15) 1.0464(8) 0.267(18) Uani 1 d . . H26A H 0.5066(24) 0.5976(15) 1.0702(8) 0.401 Uiso 1 calc R . H26B H 0.5666(24) 0.6827(15) 1.0537(8) 0.401 Uiso 1 calc R . H26C H 0.6189(24) 0.5969(15) 1.0358(8) 0.401 Uiso 1 calc R . N1B N 0.1140(9) 1.0483(7) 0.7453(3) 0.071(3) Uani 1 d . . O1B O -0.0826(9) 1.1181(7) 0.7243(3) 0.095(3) Uani 1 d . . C1B C 0.0401(12) 1.1071(9) 0.7252(4) 0.067(4) Uani 1 d . . N2B N 0.1057(10) 1.0672(7) 0.6426(3) 0.068(3) Uani 1 d . . H2B H 0.0181(10) 1.0607(7) 0.6429(3) 0.081 Uiso 1 calc R . O2B O 0.3067(10) 1.0039(7) 0.6263(3) 0.108(4) Uani 1 d . . C2B C 0.1662(11) 1.1457(8) 0.7053(3) 0.064(3) Uani 1 d . . H2B1 H 0.1873(11) 1.2016(8) 0.7163(3) 0.076 Uiso 1 calc R . O3B O 0.1010(9) 0.9459(6) 0.6115(3) 0.087(3) Uani 1 d . . C3B C 0.2482(10) 1.0753(8) 0.7270(3) 0.056(3) Uani 1 d . . H3B H 0.2796(10) 1.0335(8) 0.7070(3) 0.068 Uiso 1 calc R . C4B C 0.1645(13) 1.1450(8) 0.6593(3) 0.068(4) Uani 1 d . . H4B H 0.2596(13) 1.1491(8) 0.6498(3) 0.082 Uiso 1 calc R . C5B C 0.0841(16) 1.2203(8) 0.6413(4) 0.096(5) Uani 1 d . . H5B1 H 0.0858(16) 1.2172(8) 0.6119(4) 0.145 Uiso 1 calc R . H5B2 H 0.1259(16) 1.2720(8) 0.6500(4) 0.145 Uiso 1 calc R . H5B3 H -0.0092(16) 1.2184(8) 0.6506(4) 0.145 Uiso 1 calc R . C6B C 0.1847(14) 1.0054(10) 0.6268(4) 0.076(4) Uani 1 d . . C7B C 0.1742(16) 0.8799(10) 0.5900(6) 0.118(6) Uani 1 d . . H7B1 H 0.2309(16) 0.8483(10) 0.6089(6) 0.142 Uiso 1 calc R . H7B2 H 0.2332(16) 0.9041(10) 0.5691(6) 0.142 Uiso 1 calc R . C8B C 0.0695(14) 0.8228(8) 0.5705(5) 0.072(4) Uani 1 d . . C9B C 0.0597(20) 0.8244(11) 0.5299(6) 0.119(7) Uani 1 d . . H9B H 0.1154(20) 0.8609(11) 0.5151(6) 0.143 Uiso 1 calc R . C10B C -0.0419(38) 0.7673(19) 0.5070(7) 0.235(21) Uani 1 d . . H10B H -0.0543(38) 0.7635(19) 0.4789(7) 0.281 Uiso 1 calc R . C11B C -0.1135(27) 0.7211(19) 0.5380(8) 0.183(16) Uani 1 d . . H11B H -0.1824(27) 0.6853(19) 0.5288(8) 0.219 Uiso 1 calc R . C12B C -0.0939(23) 0.7230(15) 0.5782(11) 0.200(15) Uani 1 d . . H12B H -0.1431(23) 0.6863(15) 0.5948(11) 0.240 Uiso 1 calc R . C13B C -0.0071(21) 0.7754(13) 0.5949(7) 0.140(8) Uani 1 d . . H13B H 0.0008(21) 0.7794(13) 0.6232(7) 0.167 Uiso 1 calc R . C14B C 0.3657(11) 1.1012(8) 0.7546(3) 0.056(3) Uani 1 d . . C15B C 0.4997(13) 1.0700(9) 0.7461(4) 0.069(4) Uani 1 d . . C16B C 0.6125(14) 1.0985(10) 0.7678(4) 0.080(4) Uani 1 d . . H16B H 0.6995(14) 1.0779(10) 0.7618(4) 0.097 Uiso 1 calc R . C17B C 0.5953(14) 1.1588(10) 0.7990(4) 0.079(4) Uani 1 d . . C18B C 0.4707(16) 1.1842(11) 0.8081(4) 0.092(5) Uani 1 d . . H18B H 0.4605(16) 1.2210(11) 0.8301(4) 0.111 Uiso 1 calc R . C19B C 0.3511(13) 1.1595(10) 0.7869(4) 0.083(4) Uani 1 d . . C20B C 0.5261(12) 1.0068(9) 0.7130(4) 0.088(4) Uani 1 d . . H20D H 0.4410(12) 0.9918(9) 0.7002(4) 0.132 Uiso 1 calc R . H20E H 0.5675(12) 0.9575(9) 0.7247(4) 0.132 Uiso 1 calc R . H20F H 0.5869(12) 1.0306(9) 0.6930(4) 0.132 Uiso 1 calc R . C21B C 0.7232(17) 1.1929(13) 0.8216(5) 0.146(8) Uani 1 d . . H21D H 0.8042(17) 1.1670(13) 0.8107(5) 0.218 Uiso 1 calc R . H21E H 0.7159(17) 1.1802(13) 0.8503(5) 0.218 Uiso 1 calc R . H21F H 0.7287(17) 1.2528(13) 0.8180(5) 0.218 Uiso 1 calc R . C22B C 0.2150(15) 1.1973(10) 0.7990(4) 0.109(6) Uani 1 d . . H22D H 0.2282(15) 1.2352(10) 0.8216(4) 0.163 Uiso 1 calc R . H22E H 0.1532(15) 1.1532(10) 0.8070(4) 0.163 Uiso 1 calc R . H22F H 0.1770(15) 1.2275(10) 0.7762(4) 0.163 Uiso 1 calc R . C23B C 0.0807(16) 0.9661(11) 0.7640(5) 0.103(5) Uani 1 d . . C24B C 0.2015(18) 0.9246(12) 0.7801(7) 0.192(12) Uani 1 d . . H24D H 0.2525(18) 0.9634(12) 0.7967(7) 0.288 Uiso 1 calc R . H24E H 0.2578(18) 0.9057(12) 0.7578(7) 0.288 Uiso 1 calc R . H24F H 0.1741(18) 0.8772(12) 0.7964(7) 0.288 Uiso 1 calc R . C25B C -0.0099(29) 0.9204(13) 0.7386(7) 0.255(17) Uani 1 d . . H25D H -0.0846(29) 0.9561(13) 0.7304(7) 0.383 Uiso 1 calc R . H25E H -0.0452(29) 0.8728(13) 0.7533(7) 0.383 Uiso 1 calc R . H25F H 0.0385(29) 0.9013(13) 0.7148(7) 0.383 Uiso 1 calc R . C26B C -0.0036(23) 0.9873(15) 0.8037(6) 0.218(12) Uani 1 d . . H26D H 0.0530(23) 1.0186(15) 0.8224(6) 0.327 Uiso 1 calc R . H26E H -0.0328(23) 0.9359(15) 0.8165(6) 0.327 Uiso 1 calc R . H26F H -0.0826(23) 1.0203(15) 0.7965(6) 0.327 Uiso 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 N1A 0.050(6) 0.059(7) 0.089(7) 0.005(6) 0.007(6) 0.012(6) O1A 0.056(5) 0.120(8) 0.082(6) 0.002(6) 0.003(5) 0.021(6) C1A 0.051(8) 0.082(10) 0.086(10) 0.028(8) 0.002(7) 0.024(8) N2A 0.048(5) 0.049(6) 0.065(6) 0.009(5) 0.011(5) 0.001(6) O2A 0.047(5) 0.109(8) 0.104(7) 0.028(6) -0.002(5) -0.009(6) C2A 0.063(8) 0.043(7) 0.065(8) 0.001(6) -0.001(7) -0.005(7) O3A 0.071(6) 0.075(6) 0.076(6) 0.028(5) -0.009(5) 0.004(5) C3A 0.049(6) 0.055(8) 0.063(7) -0.001(6) 0.000(6) 0.003(6) C4A 0.053(7) 0.069(8) 0.075(8) -0.001(7) -0.001(7) -0.002(7) C5A 0.134(15) 0.060(9) 0.115(12) -0.008(8) 0.044(12) -0.008(10) C6A 0.053(8) 0.056(8) 0.076(9) 0.015(7) 0.015(7) -0.014(8) C7A 0.079(11) 0.111(13) 0.123(13) 0.041(11) -0.004(10) 0.012(11) C8A 0.065(9) 0.094(11) 0.064(9) 0.025(9) 0.026(8) 0.015(8) C9A 0.162(17) 0.056(9) 0.107(14) 0.021(9) 0.020(13) 0.003(11) C10A 0.238(37) 0.176(30) 0.121(19) 0.084(19) 0.035(20) 0.136(28) C11A 0.083(16) 0.150(27) 0.300(46) 0.084(31) 0.072(24) 0.028(15) C12A 0.109(18) 0.130(19) 0.271(35) -0.106(22) -0.020(20) -0.026(15) C13A 0.145(18) 0.134(16) 0.116(15) -0.024(14) -0.044(14) 0.008(15) C14A 0.058(7) 0.050(7) 0.059(7) 0.007(6) 0.003(6) 0.006(6) C15A 0.066(8) 0.099(11) 0.068(8) 0.018(8) 0.021(7) 0.013(8) C16A 0.103(12) 0.115(13) 0.089(11) 0.035(10) 0.000(10) -0.005(11) C17A 0.087(12) 0.144(16) 0.090(12) 0.013(11) 0.002(10) -0.015(11) C18A 0.055(8) 0.129(13) 0.083(10) -0.028(10) 0.004(8) 0.023(9) C19A 0.060(7) 0.057(8) 0.060(7) 0.002(6) -0.002(7) 0.010(7) C20A 0.114(13) 0.165(17) 0.121(13) 0.080(13) 0.037(11) 0.056(13) C21A 0.136(16) 0.226(24) 0.120(14) 0.003(15) 0.082(13) 0.000(17) C22A 0.053(7) 0.108(11) 0.101(10) -0.019(9) -0.015(8) 0.021(8) C23A 0.108(13) 0.102(13) 0.098(12) -0.027(11) 0.036(11) -0.012(11) C24A 0.280(20) 0.160(15) 0.192(17) -0.064(14) 0.033(16) -0.085(16) C25A 0.109(12) 0.077(11) 0.242(22) -0.068(14) -0.023(15) -0.003(11) C26A 0.226(26) 0.231(27) 0.345(34) -0.197(27) -0.207(27) 0.106(22) N1B 0.044(6) 0.100(9) 0.070(7) 0.004(7) 0.006(5) -0.020(7) O1B 0.058(6) 0.143(9) 0.084(6) 0.021(6) 0.014(5) 0.009(6) C1B 0.043(8) 0.099(11) 0.058(8) 0.004(7) -0.002(6) 0.032(8) N2B 0.051(6) 0.098(8) 0.053(6) -0.013(6) 0.000(5) -0.009(7) O2B 0.059(6) 0.164(11) 0.101(7) -0.034(7) -0.009(6) 0.031(7) C2B 0.047(7) 0.088(9) 0.056(8) 0.005(7) -0.003(6) 0.007(7) O3B 0.068(5) 0.097(7) 0.097(6) -0.017(6) -0.009(6) 0.024(6) C3B 0.047(6) 0.078(9) 0.045(6) -0.004(6) -0.011(6) -0.004(7) C4B 0.067(8) 0.087(10) 0.051(7) -0.012(7) -0.004(7) -0.024(8) C5B 0.105(12) 0.081(10) 0.103(11) 0.009(9) -0.039(10) -0.017(10) C6B 0.049(8) 0.126(13) 0.052(8) -0.030(9) -0.005(7) -0.006(10) C7B 0.089(11) 0.094(12) 0.171(17) -0.035(12) 0.004(12) 0.036(11) C8B 0.066(9) 0.055(8) 0.096(11) -0.017(8) 0.029(9) 0.011(7) C9B 0.163(19) 0.115(14) 0.080(12) -0.012(10) 0.010(12) 0.071(14) C10B 0.352(45) 0.244(31) 0.108(17) -0.097(20) -0.091(22) 0.261(33) C11B 0.145(22) 0.223(32) 0.180(26) -0.137(25) -0.104(21) 0.073(20) C12B 0.084(16) 0.117(19) 0.398(50) -0.069(26) -0.036(24) 0.027(14) C13B 0.110(15) 0.136(17) 0.172(19) 0.001(16) 0.076(16) -0.003(14) C14B 0.054(7) 0.081(9) 0.032(6) -0.004(6) 0.004(5) 0.003(7) C15B 0.057(7) 0.097(10) 0.055(7) 0.014(8) 0.002(7) 0.005(8) C16B 0.069(9) 0.122(13) 0.050(8) 0.040(8) -0.007(7) -0.008(9) C17B 0.061(9) 0.110(12) 0.065(9) 0.014(9) -0.017(8) -0.004(9) C18B 0.090(11) 0.132(14) 0.055(9) -0.003(9) -0.026(8) -0.025(11) C19B 0.069(9) 0.126(13) 0.054(8) -0.005(8) 0.001(7) 0.023(9) C20B 0.060(8) 0.137(13) 0.068(9) -0.001(9) 0.007(7) 0.030(9) C21B 0.126(15) 0.188(20) 0.123(14) 0.000(14) -0.055(12) -0.068(15) C22B 0.113(13) 0.138(15) 0.075(10) -0.020(10) -0.011(9) 0.036(12) C23B 0.069(9) 0.123(14) 0.117(13) 0.057(12) -0.001(10) -0.012(10) C24B 0.105(14) 0.159(20) 0.313(29) 0.163(21) -0.002(18) 0.017(14) C25B 0.347(35) 0.153(20) 0.266(29) 0.094(20) -0.194(28) -0.164(24) C26B 0.216(25) 0.248(28) 0.189(21) 0.099(21) 0.075(21) -0.019(24) _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 N1A C1A 1.339(15) . ? N1A C23A 1.44(2) . ? N1A C3A 1.484(14) . ? O1A C1A 1.233(13) . ? C1A C2A 1.49(2) . ? N2A C6A 1.327(14) . ? N2A C4A 1.446(14) . ? N2A H2A 0.86 . ? O2A C6A 1.209(13) . ? C2A C4A 1.536(15) . ? C2A C3A 1.549(14) . ? C2A H2A1 0.98 . ? O3A C6A 1.353(12) . ? O3A C7A 1.465(14) . ? C3A C14A 1.519(14) . ? C3A H3A 0.98 . ? C4A C5A 1.54(2) . ? C4A H4A 0.98 . ? C5A H5A1 0.96 . ? C5A H5A2 0.96 . ? C5A H5A3 0.96 . ? C7A C8A 1.48(2) . ? C7A H7A1 0.97 . ? C7A H7A2 0.97 . ? C8A C9A 1.31(2) . ? C8A C13A 1.38(2) . ? C9A C10A 1.39(3) . ? C9A H9A 0.93 . ? C10A C11A 1.34(3) . ? C10A H10A 0.93 . ? C11A C12A 1.33(3) . ? C11A H11A 0.93 . ? C12A C13A 1.38(3) . ? C12A H12A 0.93 . ? C13A H13A 0.93 . ? C14A C15A 1.39(2) . ? C14A C19A 1.401(15) . ? C15A C16A 1.40(2) . ? C15A C20A 1.51(2) . ? C16A C17A 1.38(2) . ? C16A H16A 0.93 . ? C17A C18A 1.37(2) . ? C17A C21A 1.54(2) . ? C18A C19A 1.41(2) . ? C18A H18A 0.93 . ? C19A C22A 1.524(15) . ? C20A H20A 0.96 . ? C20A H20B 0.96 . ? C20A H20C 0.96 . ? C21A H21A 0.96 . ? C21A H21B 0.96 . ? C21A H21C 0.96 . ? C22A H22A 0.96 . ? C22A H22B 0.96 . ? C22A H22C 0.96 . ? C23A C24A 1.47(2) . ? C23A C25A 1.47(2) . ? C23A C26A 1.50(2) . ? C24A H24A 0.96 . ? C24A H24B 0.96 . ? C24A H24C 0.96 . ? C25A H25A 0.96 . ? C25A H25B 0.96 . ? C25A H25C 0.96 . ? C26A H26A 0.96 . ? C26A H26B 0.96 . ? C26A H26C 0.96 . ? N1B C1B 1.351(14) . ? N1B C23B 1.48(2) . ? N1B C3B 1.501(13) . ? O1B C1B 1.208(13) . ? C1B C2B 1.52(2) . ? N2B C6B 1.35(2) . ? N2B C4B 1.468(13) . ? N2B H2B 0.86 . ? O2B C6B 1.189(13) . ? C2B C4B 1.502(15) . ? C2B C3B 1.547(15) . ? C2B H2B1 0.98 . ? O3B C6B 1.346(15) . ? O3B C7B 1.450(15) . ? C3B C14B 1.514(14) . ? C3B H3B 0.98 . ? C4B C5B 1.55(2) . ? C4B H4B 0.98 . ? C5B H5B1 0.96 . ? C5B H5B2 0.96 . ? C5B H5B3 0.96 . ? C7B C8B 1.51(2) . ? C7B H7B1 0.97 . ? C7B H7B2 0.97 . ? C8B C13B 1.33(2) . ? C8B C9B 1.33(2) . ? C9B C10B 1.54(3) . ? C9B H9B 0.93 . ? C10B C11B 1.43(4) . ? C10B H10B 0.93 . ? C11B C12B 1.33(3) . ? C11B H11B 0.93 . ? C12B C13B 1.31(3) . ? C12B H12B 0.93 . ? C13B H13B 0.93 . ? C14B C19B 1.41(2) . ? C14B C15B 1.42(2) . ? C15B C16B 1.38(2) . ? C15B C20B 1.50(2) . ? C16B C17B 1.41(2) . ? C16B H16B 0.93 . ? C17B C18B 1.31(2) . ? C17B C21B 1.55(2) . ? C18B C19B 1.41(2) . ? C18B H18B 0.93 . ? C19B C22B 1.51(2) . ? C20B H20D 0.96 . ? C20B H20E 0.96 . ? C20B H20F 0.96 . ? C21B H21D 0.96 . ? C21B H21E 0.96 . ? C21B H21F 0.96 . ? C22B H22D 0.96 . ? C22B H22E 0.96 . ? C22B H22F 0.96 . ? C23B C25B 1.41(2) . ? C23B C24B 1.45(2) . ? C23B C26B 1.57(2) . ? C24B H24D 0.96 . ? C24B H24E 0.96 . ? C24B H24F 0.96 . ? C25B H25D 0.96 . ? C25B H25E 0.96 . ? C25B H25F 0.96 . ? C26B H26D 0.96 . ? C26B H26E 0.96 . ? C26B H26F 0.96 . ? 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 C1A N1A C23A 133.5(12) . . ? C1A N1A C3A 94.2(10) . . ? C23A N1A C3A 130.3(11) . . ? O1A C1A N1A 130.8(14) . . ? O1A C1A C2A 135.3(13) . . ? N1A C1A C2A 93.8(10) . . ? C6A N2A C4A 122.7(9) . . ? C6A N2A H2A 118.7(6) . . ? C4A N2A H2A 118.7(6) . . ? C1A C2A C4A 115.8(10) . . ? C1A C2A C3A 85.8(8) . . ? C4A C2A C3A 116.4(10) . . ? C1A C2A H2A1 112.2(7) . . ? C4A C2A H2A1 112.2(6) . . ? C3A C2A H2A1 112.2(6) . . ? C6A O3A C7A 114.8(10) . . ? N1A C3A C14A 119.3(9) . . ? N1A C3A C2A 86.2(8) . . ? C14A C3A C2A 121.6(10) . . ? N1A C3A H3A 109.2(6) . . ? C14A C3A H3A 109.2(6) . . ? C2A C3A H3A 109.2(6) . . ? N2A C4A C2A 110.2(10) . . ? N2A C4A C5A 108.8(9) . . ? C2A C4A C5A 110.4(10) . . ? N2A C4A H4A 109.1(6) . . ? C2A C4A H4A 109.1(6) . . ? C5A C4A H4A 109.1(7) . . ? C4A C5A H5A1 109.5(7) . . ? C4A C5A H5A2 109.5(7) . . ? H5A1 C5A H5A2 109.5 . . ? C4A C5A H5A3 109.5(7) . . ? H5A1 C5A H5A3 109.5 . . ? H5A2 C5A H5A3 109.5 . . ? O2A C6A N2A 127.8(11) . . ? O2A C6A O3A 122.8(12) . . ? N2A C6A O3A 109.3(10) . . ? O3A C7A C8A 106.4(11) . . ? O3A C7A H7A1 110.4(8) . . ? C8A C7A H7A1 110.4(8) . . ? O3A C7A H7A2 110.4(8) . . ? C8A C7A H7A2 110.4(9) . . ? H7A1 C7A H7A2 108.6 . . ? C9A C8A C13A 116.6(16) . . ? C9A C8A C7A 117.1(16) . . ? C13A C8A C7A 126.3(15) . . ? C8A C9A C10A 125.2(20) . . ? C8A C9A H9A 117.4(11) . . ? C10A C9A H9A 117.4(15) . . ? C11A C10A C9A 113.3(24) . . ? C11A C10A H10A 123.4(20) . . ? C9A C10A H10A 123.4(15) . . ? C12A C11A C10A 125.4(28) . . ? C12A C11A H11A 117.3(19) . . ? C10A C11A H11A 117.3(21) . . ? C11A C12A C13A 116.2(23) . . ? C11A C12A H12A 121.9(20) . . ? C13A C12A H12A 121.9(15) . . ? C12A C13A C8A 121.0(20) . . ? C12A C13A H13A 119.5(15) . . ? C8A C13A H13A 119.5(11) . . ? C15A C14A C19A 119.1(11) . . ? C15A C14A C3A 123.0(10) . . ? C19A C14A C3A 117.8(10) . . ? C14A C15A C16A 119.5(12) . . ? C14A C15A C20A 123.4(11) . . ? C16A C15A C20A 117.1(12) . . ? C17A C16A C15A 122.3(14) . . ? C17A C16A H16A 118.9(10) . . ? C15A C16A H16A 118.9(9) . . ? C18A C17A C16A 117.7(15) . . ? C18A C17A C21A 120.2(16) . . ? C16A C17A C21A 122.1(15) . . ? C17A C18A C19A 122.0(13) . . ? C17A C18A H18A 119.0(9) . . ? C19A C18A H18A 119.0(8) . . ? C14A C19A C18A 119.1(11) . . ? C14A C19A C22A 122.8(11) . . ? C18A C19A C22A 118.0(11) . . ? C15A C20A H20A 109.5(7) . . ? C15A C20A H20B 109.5(9) . . ? H20A C20A H20B 109.47(5) . . ? C15A C20A H20C 109.5(9) . . ? H20A C20A H20C 109.5 . . ? H20B C20A H20C 109.5 . . ? C17A C21A H21A 109.5(10) . . ? C17A C21A H21B 109.5(9) . . ? H21A C21A H21B 109.47(6) . . ? C17A C21A H21C 109.5(11) . . ? H21A C21A H21C 109.5 . . ? H21B C21A H21C 109.5 . . ? C19A C22A H22A 109.5(7) . . ? C19A C22A H22B 109.5(6) . . ? H22A C22A H22B 109.5 . . ? C19A C22A H22C 109.5(7) . . ? H22A C22A H22C 109.5 . . ? H22B C22A H22C 109.5 . . ? N1A C23A C24A 105.7(14) . . ? N1A C23A C25A 112.4(13) . . ? C24A C23A C25A 111.5(17) . . ? N1A C23A C26A 113.1(16) . . ? C24A C23A C26A 105.3(18) . . ? C25A C23A C26A 108.6(14) . . ? C23A C24A H24A 109.5(12) . . ? C23A C24A H24B 109.5(10) . . ? H24A C24A H24B 109.47(8) . . ? C23A C24A H24C 109.5(12) . . ? H24A C24A H24C 109.5 . . ? H24B C24A H24C 109.5 . . ? C23A C25A H25A 109.5(10) . . ? C23A C25A H25B 109.5(10) . . ? H25A C25A H25B 109.47(5) . . ? C23A C25A H25C 109.5(8) . . ? H25A C25A H25C 109.5 . . ? H25B C25A H25C 109.5 . . ? C23A C26A H26A 109.5(14) . . ? C23A C26A H26B 109.5(12) . . ? H26A C26A H26B 109.5 . . ? C23A C26A H26C 109.5(11) . . ? H26A C26A H26C 109.5 . . ? H26B C26A H26C 109.47(7) . . ? C1B N1B C23B 134.1(11) . . ? C1B N1B C3B 94.1(9) . . ? C23B N1B C3B 127.5(11) . . ? O1B C1B N1B 129.7(13) . . ? O1B C1B C2B 137.0(12) . . ? N1B C1B C2B 93.3(9) . . ? C6B N2B C4B 122.2(10) . . ? C6B N2B H2B 118.9(7) . . ? C4B N2B H2B 118.9(6) . . ? C4B C2B C1B 114.6(10) . . ? C4B C2B C3B 117.3(11) . . ? C1B C2B C3B 85.9(8) . . ? C4B C2B H2B1 112.2(7) . . ? C1B C2B H2B1 112.2(7) . . ? C3B C2B H2B1 112.2(6) . . ? C6B O3B C7B 113.0(11) . . ? N1B C3B C14B 119.9(9) . . ? N1B C3B C2B 86.6(8) . . ? C14B C3B C2B 117.8(11) . . ? N1B C3B H3B 110.2(7) . . ? C14B C3B H3B 110.2(6) . . ? C2B C3B H3B 110.2(6) . . ? N2B C4B C2B 112.5(11) . . ? N2B C4B C5B 108.2(10) . . ? C2B C4B C5B 112.4(11) . . ? N2B C4B H4B 107.8(6) . . ? C2B C4B H4B 107.8(6) . . ? C5B C4B H4B 107.8(8) . . ? C4B C5B H5B1 109.5(7) . . ? C4B C5B H5B2 109.5(6) . . ? H5B1 C5B H5B2 109.5 . . ? C4B C5B H5B3 109.5(8) . . ? H5B1 C5B H5B3 109.5 . . ? H5B2 C5B H5B3 109.5 . . ? O2B C6B O3B 125.9(14) . . ? O2B C6B N2B 126.2(14) . . ? O3B C6B N2B 107.9(11) . . ? O3B C7B C8B 107.9(11) . . ? O3B C7B H7B1 110.1(8) . . ? C8B C7B H7B1 110.1(8) . . ? O3B C7B H7B2 110.1(8) . . ? C8B C7B H7B2 110.1(9) . . ? H7B1 C7B H7B2 108.4 . . ? C13B C8B C9B 124.8(19) . . ? C13B C8B C7B 117.9(18) . . ? C9B C8B C7B 117.2(16) . . ? C8B C9B C10B 121.3(21) . . ? C8B C9B H9B 119.3(11) . . ? C10B C9B H9B 119.3(15) . . ? C11B C10B C9B 105.8(17) . . ? C11B C10B H10B 127.1(17) . . ? C9B C10B H10B 127.1(15) . . ? C12B C11B C10B 128.2(31) . . ? C12B C11B H11B 115.9(20) . . ? C10B C11B H11B 115.9(18) . . ? C13B C12B C11B 121.4(33) . . ? C13B C12B H12B 119.3(20) . . ? C11B C12B H12B 119.3(20) . . ? C12B C13B C8B 118.2(26) . . ? C12B C13B H13B 120.9(19) . . ? C8B C13B H13B 120.9(13) . . ? C19B C14B C15B 117.8(11) . . ? C19B C14B C3B 123.2(11) . . ? C15B C14B C3B 118.9(10) . . ? C16B C15B C14B 120.9(12) . . ? C16B C15B C20B 116.9(12) . . ? C14B C15B C20B 122.1(12) . . ? C15B C16B C17B 119.9(13) . . ? C15B C16B H16B 120.0(9) . . ? C17B C16B H16B 120.0(8) . . ? C18B C17B C16B 118.9(14) . . ? C18B C17B C21B 121.8(15) . . ? C16B C17B C21B 119.3(14) . . ? C17B C18B C19B 124.4(15) . . ? C17B C18B H18B 117.8(9) . . ? C19B C18B H18B 117.8(9) . . ? C14B C19B C18B 117.9(13) . . ? C14B C19B C22B 123.1(12) . . ? C18B C19B C22B 119.0(13) . . ? C15B C20B H20D 109.5(7) . . ? C15B C20B H20E 109.5(7) . . ? H20D C20B H20E 109.5 . . ? C15B C20B H20F 109.5(7) . . ? H20D C20B H20F 109.5 . . ? H20E C20B H20F 109.5 . . ? C17B C21B H21D 109.5(10) . . ? C17B C21B H21E 109.5(8) . . ? H21D C21B H21E 109.5 . . ? C17B C21B H21F 109.5(9) . . ? H21D C21B H21F 109.5 . . ? H21E C21B H21F 109.5 . . ? C19B C22B H22D 109.5(8) . . ? C19B C22B H22E 109.5(9) . . ? H22D C22B H22E 109.5 . . ? C19B C22B H22F 109.5(8) . . ? H22D C22B H22F 109.5 . . ? H22E C22B H22F 109.5 . . ? C25B C23B C24B 119.1(20) . . ? C25B C23B N1B 110.3(14) . . ? C24B C23B N1B 112.0(13) . . ? C25B C23B C26B 105.6(18) . . ? C24B C23B C26B 102.9(15) . . ? N1B C23B C26B 105.5(15) . . ? C23B C24B H24D 109.5(12) . . ? C23B C24B H24E 109.5(12) . . ? H24D C24B H24E 109.47(7) . . ? C23B C24B H24F 109.5(9) . . ? H24D C24B H24F 109.5 . . ? H24E C24B H24F 109.5 . . ? C23B C25B H25D 109.5(13) . . ? C23B C25B H25E 109.5(11) . . ? H25D C25B H25E 109.47(7) . . ? C23B C25B H25F 109.5(15) . . ? H25D C25B H25F 109.5 . . ? H25E C25B H25F 109.5 . . ? C23B C26B H26D 109.5(11) . . ? C23B C26B H26E 109.5(11) . . ? H26D C26B H26E 109.5 . . ? C23B C26B H26F 109.5(10) . . ? H26D C26B H26F 109.5 . . ? H26E C26B H26F 109.47(6) . . ? 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 C23A N1A C1A O1A 12.6(26) . . . . ? C3A N1A C1A O1A 177.2(14) . . . . ? C23A N1A C1A C2A -163.8(15) . . . . ? C3A N1A C1A C2A 0.8(10) . . . . ? O1A C1A C2A C4A -59.6(20) . . . . ? N1A C1A C2A C4A 116.6(11) . . . . ? O1A C1A C2A C3A -176.9(16) . . . . ? N1A C1A C2A C3A -0.7(9) . . . . ? C1A N1A C3A C14A 123.6(11) . . . . ? C23A N1A C3A C14A -71.0(17) . . . . ? C1A N1A C3A C2A -0.7(10) . . . . ? C23A N1A C3A C2A 164.6(14) . . . . ? C1A C2A C3A N1A 0.7(9) . . . . ? C4A C2A C3A N1A -116.1(10) . . . . ? C1A C2A C3A C14A -121.6(11) . . . . ? C4A C2A C3A C14A 121.6(12) . . . . ? C6A N2A C4A C2A -101.3(13) . . . . ? C6A N2A C4A C5A 137.6(12) . . . . ? C1A C2A C4A N2A -35.8(14) . . . . ? C3A C2A C4A N2A 62.8(12) . . . . ? C1A C2A C4A C5A 84.5(13) . . . . ? C3A C2A C4A C5A -177.0(10) . . . . ? C4A N2A C6A O2A -0.6(21) . . . . ? C4A N2A C6A O3A -179.0(9) . . . . ? C7A O3A C6A O2A -0.3(19) . . . . ? C7A O3A C6A N2A 178.1(11) . . . . ? C6A O3A C7A C8A 170.0(11) . . . . ? O3A C7A C8A C9A 102.5(15) . . . . ? O3A C7A C8A C13A -76.0(18) . . . . ? C13A C8A C9A C10A -6.6(26) . . . . ? C7A C8A C9A C10A 174.7(17) . . . . ? C8A C9A C10A C11A 13.8(34) . . . . ? C9A C10A C11A C12A -18.1(43) . . . . ? C10A C11A C12A C13A 14.8(44) . . . . ? C11A C12A C13A C8A -5.9(32) . . . . ? C9A C8A C13A C12A 2.2(25) . . . . ? C7A C8A C13A C12A -179.2(16) . . . . ? N1A C3A C14A C15A -50.0(16) . . . . ? C2A C3A C14A C15A 54.8(16) . . . . ? N1A C3A C14A C19A 131.0(11) . . . . ? C2A C3A C14A C19A -124.2(12) . . . . ? C19A C14A C15A C16A -2.9(20) . . . . ? C3A C14A C15A C16A 178.2(13) . . . . ? C19A C14A C15A C20A 178.5(14) . . . . ? C3A C14A C15A C20A -0.4(22) . . . . ? C14A C15A C16A C17A 1.2(25) . . . . ? C20A C15A C16A C17A 179.9(17) . . . . ? C15A C16A C17A C18A 3.1(27) . . . . ? C15A C16A C17A C21A -176.5(16) . . . . ? C16A C17A C18A C19A -5.7(25) . . . . ? C21A C17A C18A C19A 173.8(15) . . . . ? C15A C14A C19A C18A 0.3(18) . . . . ? C3A C14A C19A C18A 179.4(11) . . . . ? C15A C14A C19A C22A -176.2(12) . . . . ? C3A C14A C19A C22A 2.8(18) . . . . ? C17A C18A C19A C14A 4.1(21) . . . . ? C17A C18A C19A C22A -179.2(14) . . . . ? C1A N1A C23A C24A 60.2(23) . . . . ? C3A N1A C23A C24A -99.5(19) . . . . ? C1A N1A C23A C25A -177.9(14) . . . . ? C3A N1A C23A C25A 22.4(22) . . . . ? C1A N1A C23A C26A -54.5(24) . . . . ? C3A N1A C23A C26A 145.8(16) . . . . ? C23B N1B C1B O1B 18.5(26) . . . . ? C3B N1B C1B O1B 175.4(15) . . . . ? C23B N1B C1B C2B -159.5(14) . . . . ? C3B N1B C1B C2B -2.6(11) . . . . ? O1B C1B C2B C4B -56.9(23) . . . . ? N1B C1B C2B C4B 120.8(11) . . . . ? O1B C1B C2B C3B -175.2(17) . . . . ? N1B C1B C2B C3B 2.5(10) . . . . ? C1B N1B C3B C14B 122.9(12) . . . . ? C23B N1B C3B C14B -77.9(18) . . . . ? C1B N1B C3B C2B 2.6(10) . . . . ? C23B N1B C3B C2B 161.7(13) . . . . ? C4B C2B C3B N1B -117.9(11) . . . . ? C1B C2B C3B N1B -2.3(9) . . . . ? C4B C2B C3B C14B 119.9(12) . . . . ? C1B C2B C3B C14B -124.5(10) . . . . ? C6B N2B C4B C2B -103.1(14) . . . . ? C6B N2B C4B C5B 132.1(13) . . . . ? C1B C2B C4B N2B -38.7(15) . . . . ? C3B C2B C4B N2B 59.8(14) . . . . ? C1B C2B C4B C5B 83.7(14) . . . . ? C3B C2B C4B C5B -177.8(10) . . . . ? C7B O3B C6B O2B -5.3(22) . . . . ? C7B O3B C6B N2B 174.3(12) . . . . ? C4B N2B C6B O2B 4.0(23) . . . . ? C4B N2B C6B O3B -175.5(10) . . . . ? C6B O3B C7B C8B -174.0(12) . . . . ? O3B C7B C8B C13B -68.9(18) . . . . ? O3B C7B C8B C9B 110.2(15) . . . . ? C13B C8B C9B C10B -2.1(25) . . . . ? C7B C8B C9B C10B 178.8(14) . . . . ? C8B C9B C10B C11B 1.4(26) . . . . ? C9B C10B C11B C12B -2.9(36) . . . . ? C10B C11B C12B C13B 5.1(42) . . . . ? C11B C12B C13B C8B -5.1(32) . . . . ? C9B C8B C13B C12B 3.9(27) . . . . ? C7B C8B C13B C12B -177.1(16) . . . . ? N1B C3B C14B C19B -49.4(18) . . . . ? C2B C3B C14B C19B 53.6(15) . . . . ? N1B C3B C14B C15B 135.0(12) . . . . ? C2B C3B C14B C15B -122.0(12) . . . . ? C19B C14B C15B C16B -2.4(19) . . . . ? C3B C14B C15B C16B 173.4(11) . . . . ? C19B C14B C15B C20B 178.9(12) . . . . ? C3B C14B C15B C20B -5.3(19) . . . . ? C14B C15B C16B C17B 0.5(19) . . . . ? C20B C15B C16B C17B 179.2(12) . . . . ? C15B C16B C17B C18B 2.9(21) . . . . ? C15B C16B C17B C21B -177.3(13) . . . . ? C16B C17B C18B C19B -4.5(24) . . . . ? C21B C17B C18B C19B 175.8(15) . . . . ? C15B C14B C19B C18B 1.1(19) . . . . ? C3B C14B C19B C18B -174.5(12) . . . . ? C15B C14B C19B C22B -180.0(13) . . . . ? C3B C14B C19B C22B 4.4(21) . . . . ? C17B C18B C19B C14B 2.5(24) . . . . ? C17B C18B C19B C22B -176.6(16) . . . . ? C1B N1B C23B C25B 41.2(25) . . . . ? C3B N1B C23B C25B -109.2(19) . . . . ? C1B N1B C23B C24B 176.4(16) . . . . ? C3B N1B C23B C24B 26.0(22) . . . . ? C1B N1B C23B C26B -72.4(20) . . . . ? C3B N1B C23B C26B 137.2(13) . . . . ? _refine_diff_density_max 0.238 _refine_diff_density_min -0.164 _refine_diff_density_rms 0.044 data_s672rm _database_code_CSD 165012 _publ_contact_author ' Joachim Podlech' _publ_contact_author_email joachim.podlech@po.uni-stuttgart.de loop_ _publ_author_name 'Michael R. Linder' 'Wolfgang U. Frey' 'Joachim Podlech' _journal_name_full 'Journal of the Chemical Society, Perkin Transactions 1' _journal_coden_Cambridge 207 _audit_creation_method SHELXL _chemical_name_systematic ; (E,3S,4S,1'S)-1-Allyl-3-[1-(benzyloxycarbonylamino)-2-methylpropyl]- 4-(2-phenylethenyl)-azetidin-2-one # The configuration has been determined relative to the configuration at 1' # which is given by the synthetic precursors ; _chemical_name_common ? _chemical_formula_moiety ? _chemical_formula_structural ? _chemical_formula_analytical ? _chemical_formula_sum 'C26 H30 N2 O3' _chemical_formula_weight 418.52 _chemical_melting_point '373 - 374 K' _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' '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' _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M P2(1) loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z' _cell_length_a 10.158(2) _cell_length_b 9.524(2) _cell_length_c 12.5834(15) _cell_angle_alpha 90.00 _cell_angle_beta 97.301(12) _cell_angle_gamma 90.00 _cell_volume 1207.5(3) _cell_formula_units_Z 2 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 26 _cell_measurement_theta_min 16 _cell_measurement_theta_max 17 _exptl_crystal_description block _exptl_crystal_colour colourless _exptl_crystal_size_max 1.00 _exptl_crystal_size_mid 0.70 _exptl_crystal_size_min 0.35 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.151 _exptl_crystal_density_method ? _exptl_crystal_F_000 448 _exptl_absorpt_coefficient_mu 0.075 _exptl_absorpt_correction_type none _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 293(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device Nicolet P3 _diffrn_measurement_method Wyckoff - Scan _diffrn_standards_number 3 _diffrn_standards_interval_count 50 _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 2947 _diffrn_reflns_av_R_equivalents 0.0115 _diffrn_reflns_av_sigmaI/netI 0.0211 _diffrn_reflns_limit_h_min 0 _diffrn_reflns_limit_h_max 12 _diffrn_reflns_limit_k_min 0 _diffrn_reflns_limit_k_max 12 _diffrn_reflns_limit_l_min -16 _diffrn_reflns_limit_l_max 15 _diffrn_reflns_theta_min 1.63 _diffrn_reflns_theta_max 27.00 _reflns_number_total 2793 _reflns_number_observed 2291 _reflns_observed_criterion >2sigma(I) _computing_data_collection Siemens P3/PC Data Collection System _computing_cell_refinement Siemens P3/PC Data Collection System _computing_data_reduction SHELXTL plus - XDISK _computing_structure_solution 'SHELXS-86 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-93 (Sheldrick, 1993)' _computing_molecular_graphics SHELXTL - XP _computing_publication_material ? _refine_special_details ; Refinement on F^2^ for ALL reflections except for 145 with very negative F^2^ or flagged by the user for potential systematic errors. Weighted R-factors wR and all goodnesses 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 observed criterion of F^2^ > 2sigma(F^2^) is used only for calculating _R_factor_obs 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 w=1/[\s^2^(Fo^2^)+(0.0590P)^2^+0.1284P] 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 ? _refine_ls_extinction_method SHELXL _refine_ls_extinction_coef 0.0237(39) _refine_ls_extinction_expression 'Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^' _refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _refine_ls_abs_structure_Flack -2.60(177) _refine_ls_number_reflns 2648 _refine_ls_number_parameters 281 _refine_ls_number_restraints 14 _refine_ls_R_factor_all 0.0575 _refine_ls_R_factor_obs 0.0437 _refine_ls_wR_factor_all 0.1285 _refine_ls_wR_factor_obs 0.1119 _refine_ls_goodness_of_fit_all 1.074 _refine_ls_goodness_of_fit_obs 1.113 _refine_ls_restrained_S_all 1.171 _refine_ls_restrained_S_obs 1.143 _refine_ls_shift/esd_max 0.000 _refine_ls_shift/esd_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_thermal_displace_type _atom_site_occupancy _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_group N1 N -0.3906(2) 0.7148(3) 0.4117(2) 0.0605(7) Uani 1 d . . C1 C -0.3776(3) 0.7319(4) 0.5187(2) 0.0587(7) Uani 1 d . . O1 O -0.4328(2) 0.6755(4) 0.5869(2) 0.0871(8) Uani 1 d . . N2 N -0.0248(2) 0.8674(2) 0.5315(2) 0.0482(5) Uani 1 d . . H2 H -0.0179(2) 0.9559(2) 0.5446(2) 0.058 Uiso 1 calc R . O2 O 0.0689(2) 0.6810(2) 0.4567(2) 0.0692(6) Uani 1 d . . C2 C -0.2650(3) 0.8392(3) 0.5161(2) 0.0487(6) Uani 1 d . . H2A H -0.2882(3) 0.9339(3) 0.5377(2) 0.058 Uiso 1 calc R . O3 O 0.1433(2) 0.9025(2) 0.4395(2) 0.0615(5) Uani 1 d . . C3 C -0.2866(3) 0.8160(3) 0.3924(2) 0.0496(6) Uani 1 d . . H3 H -0.2103(3) 0.7693(3) 0.3672(2) 0.059 Uiso 1 calc R . C4 C -0.1314(3) 0.7879(3) 0.5716(2) 0.0469(6) Uani 1 d . . H4 H -0.1218(3) 0.6903(3) 0.5492(2) 0.056 Uiso 1 calc R . C5 C -0.1217(3) 0.7869(3) 0.6942(2) 0.0618(8) Uani 1 d . . H5 H -0.1967(3) 0.7319(3) 0.7135(2) 0.074 Uiso 1 calc R . C6 C 0.0048(4) 0.7136(4) 0.7427(3) 0.0798(10) Uani 1 d . . H6A H 0.0090(4) 0.6219(4) 0.7116(3) 0.120 Uiso 1 calc R . H6B H 0.0050(4) 0.7050(4) 0.8187(3) 0.120 Uiso 1 calc R . H6C H 0.0803(4) 0.7677(4) 0.7283(3) 0.120 Uiso 1 calc R . C7 C -0.1314(5) 0.9329(5) 0.7418(3) 0.0931(13) Uani 1 d . . H7A H -0.2119(5) 0.9773(5) 0.7102(3) 0.140 Uiso 1 calc R . H7B H -0.0566(5) 0.9881(5) 0.7274(3) 0.140 Uiso 1 calc R . H7C H -0.1319(5) 0.9254(5) 0.8179(3) 0.140 Uiso 1 calc R . C8 C 0.0618(3) 0.8062(3) 0.4752(2) 0.0506(6) Uani 1 d . . C9 C 0.2387(3) 0.8516(4) 0.3714(3) 0.0677(8) Uani 1 d . . H9A H 0.2540(3) 0.7522(4) 0.3842(3) 0.081 Uiso 1 calc R . H9B H 0.3225(3) 0.9002(4) 0.3897(3) 0.081 Uiso 1 calc R . C10 C 0.1902(3) 0.8748(3) 0.2560(3) 0.0610(7) Uani 1 d . . C11 C 0.0781(4) 0.8071(4) 0.2048(3) 0.0751(9) Uani 1 d . . H11 H 0.0314(4) 0.7447(4) 0.2429(3) 0.090 Uiso 1 calc R . C12 C 0.0363(4) 0.8320(5) 0.0986(4) 0.0916(12) Uani 1 d . . H12 H -0.0383(4) 0.7860(5) 0.0649(4) 0.110 Uiso 1 calc R . C13 C 0.1039(5) 0.9243(6) 0.0419(3) 0.0971(13) Uani 1 d . . H13 H 0.0743(5) 0.9409(6) -0.0300(3) 0.117 Uiso 1 calc R . C14 C 0.2133(5) 0.9914(5) 0.0894(3) 0.0902(12) Uani 1 d . . H14 H 0.2591(5) 1.0535(5) 0.0503(3) 0.108 Uiso 1 calc R . C15 C 0.2564(4) 0.9671(4) 0.1965(3) 0.0736(9) Uani 1 d . . H15 H 0.3314(4) 1.0136(4) 0.2291(3) 0.088 Uiso 1 calc R . C16 C -0.4621(4) 0.6158(5) 0.3399(3) 0.0940(13) Uani 1 d . . H16A H -0.5072(4) 0.6641(5) 0.2779(3) 0.113 Uiso 1 calc R . H16B H -0.5279(4) 0.5672(5) 0.3757(3) 0.113 Uiso 1 calc R . C17 C -0.3602(7) 0.5092(6) 0.3047(5) 0.138(2) Uani 1 d DU . H17 H -0.3279(7) 0.4398(6) 0.3531(5) 0.165 Uiso 1 calc R . C18 C -0.3184(8) 0.5113(9) 0.2138(7) 0.178(3) Uani 1 d DU . H18A H -0.3489(8) 0.5795(9) 0.1638(7) 0.214 Uiso 1 calc R . H18B H -0.2573(8) 0.4446(9) 0.1973(7) 0.214 Uiso 1 calc R . C19 C -0.3363(3) 0.9346(3) 0.3208(2) 0.0536(6) Uani 1 d . . H19 H -0.3994(3) 0.9949(3) 0.3433(2) 0.064 Uiso 1 calc R . C20 C -0.2954(3) 0.9580(3) 0.2277(2) 0.0531(6) Uani 1 d . . H20 H -0.2259(3) 0.9020(3) 0.2109(2) 0.064 Uiso 1 calc R . C21 C -0.3468(3) 1.0627(3) 0.1465(2) 0.0519(6) Uani 1 d . . C22 C -0.4433(3) 1.1602(3) 0.1628(2) 0.0620(8) Uani 1 d . . H22 H -0.4753(3) 1.1641(3) 0.2288(2) 0.074 Uiso 1 calc R . C23 C -0.4926(4) 1.2513(4) 0.0826(3) 0.0766(9) Uani 1 d . . H23 H -0.5574(4) 1.3163(4) 0.0948(3) 0.092 Uiso 1 calc R . C24 C -0.4458(4) 1.2466(4) -0.0164(3) 0.0813(11) Uani 1 d . . H24 H -0.4803(4) 1.3068(4) -0.0712(3) 0.098 Uiso 1 calc R . C25 C -0.3498(4) 1.1537(5) -0.0325(3) 0.0790(11) Uani 1 d . . H25 H -0.3174(4) 1.1517(5) -0.0984(3) 0.095 Uiso 1 calc R . C26 C -0.2989(3) 1.0620(4) 0.0470(2) 0.0683(8) Uani 1 d . . H26 H -0.2324(3) 0.9993(4) 0.0345(2) 0.082 Uiso 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 N1 0.0643(14) 0.063(2) 0.0540(13) 0.0057(11) 0.0083(11) -0.0144(12) C1 0.0511(15) 0.068(2) 0.059(2) 0.0106(14) 0.0129(12) 0.0013(14) O1 0.0742(14) 0.121(2) 0.0706(14) 0.023(2) 0.0289(12) -0.018(2) N2 0.0592(13) 0.0322(10) 0.0544(13) -0.0021(9) 0.0122(10) -0.0013(10) O2 0.0855(15) 0.0368(10) 0.091(2) -0.0034(10) 0.0328(12) 0.0017(10) C2 0.0580(15) 0.0470(14) 0.0418(12) 0.0032(11) 0.0097(11) 0.0051(12) O3 0.0704(13) 0.0484(11) 0.0703(13) -0.0058(9) 0.0265(10) -0.0084(10) C3 0.0536(14) 0.0529(15) 0.0432(13) 0.0025(11) 0.0103(11) 0.0003(12) C4 0.0568(15) 0.0349(11) 0.0493(14) 0.0017(11) 0.0075(11) -0.0016(11) C5 0.078(2) 0.057(2) 0.0490(15) 0.0088(13) 0.0047(14) -0.0029(15) C6 0.086(2) 0.075(2) 0.073(2) 0.019(2) -0.013(2) 0.002(2) C7 0.143(4) 0.082(3) 0.053(2) -0.008(2) 0.006(2) 0.017(3) C8 0.061(2) 0.0378(13) 0.0533(15) 0.0019(11) 0.0080(12) 0.0001(12) C9 0.059(2) 0.068(2) 0.079(2) 0.001(2) 0.0218(15) 0.003(2) C10 0.062(2) 0.052(2) 0.072(2) -0.0121(15) 0.0221(14) 0.0028(14) C11 0.069(2) 0.063(2) 0.094(3) -0.013(2) 0.013(2) -0.002(2) C12 0.083(2) 0.092(3) 0.097(3) -0.030(2) 0.000(2) 0.003(2) C13 0.113(3) 0.109(3) 0.070(2) -0.010(2) 0.012(2) 0.014(3) C14 0.117(3) 0.087(3) 0.072(2) -0.003(2) 0.029(2) -0.004(3) C15 0.080(2) 0.067(2) 0.078(2) -0.015(2) 0.028(2) -0.005(2) C16 0.098(3) 0.102(3) 0.078(2) 0.001(2) -0.007(2) -0.036(3) C17 0.222(6) 0.096(4) 0.093(3) -0.029(3) 0.013(4) -0.035(4) C18 0.190(7) 0.139(6) 0.197(8) -0.031(6) -0.007(6) 0.023(6) C19 0.0540(14) 0.059(2) 0.0479(13) 0.0073(13) 0.0066(11) 0.0022(13) C20 0.0533(14) 0.055(2) 0.0513(14) 0.0053(12) 0.0088(11) -0.0014(13) C21 0.0566(15) 0.0491(15) 0.0488(14) 0.0046(11) 0.0023(11) -0.0117(12) C22 0.071(2) 0.057(2) 0.058(2) 0.0082(14) 0.0076(14) -0.0047(15) C23 0.082(2) 0.062(2) 0.083(2) 0.013(2) 0.004(2) 0.004(2) C24 0.094(3) 0.077(2) 0.068(2) 0.031(2) -0.009(2) -0.010(2) C25 0.093(2) 0.092(3) 0.051(2) 0.021(2) 0.009(2) -0.007(2) C26 0.072(2) 0.080(2) 0.053(2) 0.011(2) 0.0116(14) 0.000(2) _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 N1 C1 1.345(4) . ? N1 C16 1.437(5) . ? N1 C3 1.473(4) . ? C1 O1 1.209(3) . ? C1 C2 1.537(4) . ? N2 C8 1.332(3) . ? N2 C4 1.462(3) . ? N2 H2 0.86 . ? O2 C8 1.218(3) . ? C2 C4 1.525(4) . ? C2 C3 1.560(3) . ? C2 H2A 0.98 . ? O3 C8 1.350(3) . ? O3 C9 1.456(3) . ? C3 C19 1.493(4) . ? C3 H3 0.98 . ? C4 C5 1.533(4) . ? C4 H4 0.98 . ? C5 C6 1.521(5) . ? C5 C7 1.523(5) . ? C5 H5 0.98 . ? C6 H6A 0.96 . ? C6 H6B 0.96 . ? C6 H6C 0.96 . ? C7 H7A 0.96 . ? C7 H7B 0.96 . ? C7 H7C 0.96 . ? C9 C10 1.489(5) . ? C9 H9A 0.97 . ? C9 H9B 0.97 . ? C10 C15 1.384(5) . ? C10 C11 1.394(5) . ? C11 C12 1.370(6) . ? C11 H11 0.93 . ? C12 C13 1.371(6) . ? C12 H12 0.93 . ? C13 C14 1.354(6) . ? C13 H13 0.93 . ? C14 C15 1.382(5) . ? C14 H14 0.93 . ? C15 H15 0.93 . ? C16 C17 1.554(8) . ? C16 H16A 0.97 . ? C16 H16B 0.97 . ? C17 C18 1.270(6) . ? C17 H17 0.93 . ? C18 H18A 0.93 . ? C18 H18B 0.93 . ? C19 C20 1.311(4) . ? C19 H19 0.93 . ? C20 C21 1.474(4) . ? C20 H20 0.93 . ? C21 C22 1.385(4) . ? C21 C26 1.400(4) . ? C22 C23 1.376(5) . ? C22 H22 0.93 . ? C23 C24 1.391(5) . ? C23 H23 0.93 . ? C24 C25 1.351(6) . ? C24 H24 0.93 . ? C25 C26 1.378(5) . ? C25 H25 0.93 . ? C26 H26 0.93 . ? 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 C1 N1 C16 133.3(3) . . ? C1 N1 C3 96.0(2) . . ? C16 N1 C3 129.9(3) . . ? O1 C1 N1 131.3(3) . . ? O1 C1 C2 136.4(3) . . ? N1 C1 C2 92.2(2) . . ? C8 N2 C4 121.6(2) . . ? C8 N2 H2 119.18(14) . . ? C4 N2 H2 119.18(13) . . ? C4 C2 C1 113.5(2) . . ? C4 C2 C3 114.6(2) . . ? C1 C2 C3 85.2(2) . . ? C4 C2 H2A 113.54(14) . . ? C1 C2 H2A 113.54(15) . . ? C3 C2 H2A 113.54(14) . . ? C8 O3 C9 116.9(2) . . ? N1 C3 C19 113.6(2) . . ? N1 C3 C2 86.6(2) . . ? C19 C3 C2 119.3(2) . . ? N1 C3 H3 111.7(2) . . ? C19 C3 H3 111.7(2) . . ? C2 C3 H3 111.68(14) . . ? N2 C4 C2 109.3(2) . . ? N2 C4 C5 113.2(2) . . ? C2 C4 C5 113.8(2) . . ? N2 C4 H4 106.69(13) . . ? C2 C4 H4 106.69(14) . . ? C5 C4 H4 106.7(2) . . ? C6 C5 C7 110.8(3) . . ? C6 C5 C4 110.4(3) . . ? C7 C5 C4 113.0(2) . . ? C6 C5 H5 107.4(2) . . ? C7 C5 H5 107.4(2) . . ? C4 C5 H5 107.4(2) . . ? C5 C6 H6A 109.5(2) . . ? C5 C6 H6B 109.5(2) . . ? H6A C6 H6B 109.5 . . ? C5 C6 H6C 109.5(2) . . ? H6A C6 H6C 109.5 . . ? H6B C6 H6C 109.5 . . ? C5 C7 H7A 109.5(2) . . ? C5 C7 H7B 109.5(2) . . ? H7A C7 H7B 109.5 . . ? C5 C7 H7C 109.5(2) . . ? H7A C7 H7C 109.5 . . ? H7B C7 H7C 109.5 . . ? O2 C8 N2 126.1(3) . . ? O2 C8 O3 123.2(3) . . ? N2 C8 O3 110.7(2) . . ? O3 C9 C10 111.2(3) . . ? O3 C9 H9A 109.4(2) . . ? C10 C9 H9A 109.4(2) . . ? O3 C9 H9B 109.4(2) . . ? C10 C9 H9B 109.4(2) . . ? H9A C9 H9B 108.0 . . ? C15 C10 C11 117.9(3) . . ? C15 C10 C9 119.9(3) . . ? C11 C10 C9 122.1(3) . . ? C12 C11 C10 120.3(4) . . ? C12 C11 H11 119.9(3) . . ? C10 C11 H11 119.9(2) . . ? C11 C12 C13 120.4(4) . . ? C11 C12 H12 119.8(3) . . ? C13 C12 H12 119.8(3) . . ? C14 C13 C12 120.7(4) . . ? C14 C13 H13 119.7(3) . . ? C12 C13 H13 119.7(3) . . ? C13 C14 C15 119.5(4) . . ? C13 C14 H14 120.3(3) . . ? C15 C14 H14 120.3(3) . . ? C14 C15 C10 121.3(4) . . ? C14 C15 H15 119.4(3) . . ? C10 C15 H15 119.4(2) . . ? N1 C16 C17 107.8(4) . . ? N1 C16 H16A 110.1(2) . . ? C17 C16 H16A 110.1(3) . . ? N1 C16 H16B 110.1(2) . . ? C17 C16 H16B 110.1(3) . . ? H16A C16 H16B 108.5 . . ? C18 C17 C16 123.9(7) . . ? C18 C17 H17 118.1(5) . . ? C16 C17 H17 118.1(3) . . ? C17 C18 H18A 120.0(5) . . ? C17 C18 H18B 120.0(5) . . ? H18A C18 H18B 120.0 . . ? C20 C19 C3 123.1(3) . . ? C20 C19 H19 118.4(2) . . ? C3 C19 H19 118.4(2) . . ? C19 C20 C21 127.5(3) . . ? C19 C20 H20 116.2(2) . . ? C21 C20 H20 116.2(2) . . ? C22 C21 C26 117.9(3) . . ? C22 C21 C20 123.1(2) . . ? C26 C21 C20 118.9(3) . . ? C23 C22 C21 120.9(3) . . ? C23 C22 H22 119.6(2) . . ? C21 C22 H22 119.6(2) . . ? C22 C23 C24 120.2(4) . . ? C22 C23 H23 119.9(2) . . ? C24 C23 H23 119.9(2) . . ? C25 C24 C23 119.4(3) . . ? C25 C24 H24 120.3(2) . . ? C23 C24 H24 120.3(2) . . ? C24 C25 C26 121.2(3) . . ? C24 C25 H25 119.4(2) . . ? C26 C25 H25 119.4(2) . . ? C25 C26 C21 120.4(3) . . ? C25 C26 H26 119.8(2) . . ? C21 C26 H26 119.8(2) . . ? 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 C16 N1 C1 O1 -7.7(6) . . . . ? C3 N1 C1 O1 -177.8(4) . . . . ? C16 N1 C1 C2 169.3(4) . . . . ? C3 N1 C1 C2 -0.8(2) . . . . ? O1 C1 C2 C4 62.7(5) . . . . ? N1 C1 C2 C4 -114.0(2) . . . . ? O1 C1 C2 C3 177.5(4) . . . . ? N1 C1 C2 C3 0.8(2) . . . . ? C1 N1 C3 C19 -119.8(3) . . . . ? C16 N1 C3 C19 69.6(4) . . . . ? C1 N1 C3 C2 0.8(2) . . . . ? C16 N1 C3 C2 -169.8(4) . . . . ? C4 C2 C3 N1 112.9(2) . . . . ? C1 C2 C3 N1 -0.7(2) . . . . ? C4 C2 C3 C19 -131.8(3) . . . . ? C1 C2 C3 C19 114.6(3) . . . . ? C8 N2 C4 C2 -114.4(3) . . . . ? C8 N2 C4 C5 117.6(3) . . . . ? C1 C2 C4 N2 158.5(2) . . . . ? C3 C2 C4 N2 62.8(3) . . . . ? C1 C2 C4 C5 -73.9(3) . . . . ? C3 C2 C4 C5 -169.5(2) . . . . ? N2 C4 C5 C6 -63.3(3) . . . . ? C2 C4 C5 C6 171.2(3) . . . . ? N2 C4 C5 C7 61.5(4) . . . . ? C2 C4 C5 C7 -64.1(4) . . . . ? C4 N2 C8 O2 -5.0(5) . . . . ? C4 N2 C8 O3 174.8(2) . . . . ? C9 O3 C8 O2 3.2(4) . . . . ? C9 O3 C8 N2 -176.6(2) . . . . ? C8 O3 C9 C10 98.3(3) . . . . ? O3 C9 C10 C15 114.3(3) . . . . ? O3 C9 C10 C11 -65.1(4) . . . . ? C15 C10 C11 C12 0.2(5) . . . . ? C9 C10 C11 C12 179.6(3) . . . . ? C10 C11 C12 C13 -0.3(6) . . . . ? C11 C12 C13 C14 0.5(7) . . . . ? C12 C13 C14 C15 -0.4(7) . . . . ? C13 C14 C15 C10 0.3(6) . . . . ? C11 C10 C15 C14 -0.2(5) . . . . ? C9 C10 C15 C14 -179.6(3) . . . . ? C1 N1 C16 C17 -104.2(5) . . . . ? C3 N1 C16 C17 62.9(5) . . . . ? N1 C16 C17 C18 -103.6(7) . . . . ? N1 C3 C19 C20 -117.6(3) . . . . ? C2 C3 C19 C20 142.6(3) . . . . ? C3 C19 C20 C21 173.5(3) . . . . ? C19 C20 C21 C22 4.7(5) . . . . ? C19 C20 C21 C26 -173.5(3) . . . . ? C26 C21 C22 C23 1.4(5) . . . . ? C20 C21 C22 C23 -176.9(3) . . . . ? C21 C22 C23 C24 0.0(5) . . . . ? C22 C23 C24 C25 -1.3(6) . . . . ? C23 C24 C25 C26 1.1(6) . . . . ? C24 C25 C26 C21 0.4(6) . . . . ? C22 C21 C26 C25 -1.7(5) . . . . ? C20 C21 C26 C25 176.7(3) . . . . ? _refine_diff_density_max 0.142 _refine_diff_density_min -0.164 _refine_diff_density_rms 0.026 data_s728rc1 _database_code_CSD 165013 _publ_contact_author ' Joachim Podlech' _publ_contact_author_email joachim.podlech@po.uni-stuttgart.de loop_ _publ_author_name 'Michael R. Linder' 'Wolfgang U. Frey' 'Joachim Podlech' _journal_name_full 'Journal of the Chemical Society, Perkin Transactions 1' _journal_coden_Cambridge 207 _audit_creation_method SHELXL _chemical_name_systematic ; (3R,4R,1'S)-4-Acetoxy-1-benzyl-3-[1-(benzyloxycarbonylamino)ethyl]- azetidin-2-one # The configuration has been determined relative to the configuration at 1' # which is given by the synthetic precursors ; _chemical_name_common ? _chemical_formula_moiety ? _chemical_formula_structural ? _chemical_formula_analytical ? _chemical_formula_sum 'C22 H24 N2 O5' _chemical_formula_weight 396.43 _chemical_melting_point '362 - 364 K' _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' 0.0181 0.0091 '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' 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 'O' 'O' 0.0492 0.0322 '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) loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z' _cell_length_a 12.3571(6) _cell_length_b 9.1315(9) _cell_length_c 19.0056(8) _cell_angle_alpha 90.00 _cell_angle_beta 94.281(4) _cell_angle_gamma 90.00 _cell_volume 2138.6(3) _cell_formula_units_Z 4 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 40 _cell_measurement_theta_min 22 _cell_measurement_theta_max 25 _exptl_crystal_description block _exptl_crystal_colour colourless _exptl_crystal_size_max 1.20 _exptl_crystal_size_mid 0.25 _exptl_crystal_size_min 0.15 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.231 _exptl_crystal_density_method ? _exptl_crystal_F_000 840 _exptl_absorpt_coefficient_mu 0.722 _exptl_absorpt_correction_type none _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 293(2) _diffrn_radiation_wavelength 1.54178 _diffrn_radiation_type CuK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device Siemens P4 _diffrn_measurement_method Omega - Scan _diffrn_standards_number 3 _diffrn_standards_interval_count 100 _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 8083 _diffrn_reflns_av_R_equivalents 0.0204 _diffrn_reflns_av_sigmaI/netI 0.0419 _diffrn_reflns_limit_h_min -14 _diffrn_reflns_limit_h_max 14 _diffrn_reflns_limit_k_min -10 _diffrn_reflns_limit_k_max 9 _diffrn_reflns_limit_l_min -22 _diffrn_reflns_limit_l_max 22 _diffrn_reflns_theta_min 2.33 _diffrn_reflns_theta_max 67.99 _reflns_number_total 6922 _reflns_number_observed 4840 _reflns_observed_criterion >2sigma(I) _computing_data_collection Siemens XSCANS _computing_cell_refinement Siemens XSCANS _computing_data_reduction SHELXTL plus - XDISK _computing_structure_solution 'SHELXS-86 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-93 (Sheldrick, 1993)' _computing_molecular_graphics SHELXTL - XP _computing_publication_material ? _refine_special_details ; Refinement on F^2^ for ALL reflections except for 373 with very negative F^2^ or flagged by the user for potential systematic errors. Weighted R-factors wR and all goodnesses 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 observed criterion of F^2^ > 2sigma(F^2^) is used only for calculating _R_factor_obs 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 w=1/[\s^2^(Fo^2^)+(0.1023P)^2^+0.0123P] 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 ? _refine_ls_extinction_method SHELXL _refine_ls_extinction_coef 0.0061(6) _refine_ls_extinction_expression 'Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^' _refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _refine_ls_abs_structure_Flack -0.16(28) _refine_ls_number_reflns 6549 _refine_ls_number_parameters 524 _refine_ls_number_restraints 25 _refine_ls_R_factor_all 0.0795 _refine_ls_R_factor_obs 0.0580 _refine_ls_wR_factor_all 0.1908 _refine_ls_wR_factor_obs 0.1553 _refine_ls_goodness_of_fit_all 1.099 _refine_ls_goodness_of_fit_obs 1.127 _refine_ls_restrained_S_all 1.165 _refine_ls_restrained_S_obs 1.160 _refine_ls_shift/esd_max -0.002 _refine_ls_shift/esd_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_thermal_displace_type _atom_site_occupancy _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_group O1A O -0.2352(3) 0.4943(4) -0.1471(2) 0.0979(10) Uani 1 d . . N1A N -0.1079(3) 0.3247(4) -0.1823(2) 0.0802(9) Uani 1 d . . C1A C -0.1827(3) 0.3818(5) -0.1410(2) 0.0729(10) Uani 1 d . . N2A N -0.0342(2) 0.3711(3) -0.0046(2) 0.0598(7) Uani 1 d . . H2NA H -0.0345(2) 0.4631(3) -0.0143(2) 0.072 Uiso 1 calc R . C2A C -0.0826(3) 0.2015(4) -0.1361(2) 0.0692(9) Uani 1 d . . H2A H -0.0088(3) 0.2041(4) -0.1133(2) 0.083 Uiso 1 calc R . O2A O 0.0719(2) 0.1780(3) 0.0289(2) 0.0817(8) Uani 1 d . . O3A O 0.1409(2) 0.4053(3) 0.02419(14) 0.0705(7) Uani 1 d . . C3A C -0.1682(3) 0.2550(4) -0.0891(2) 0.0612(8) Uani 1 d . . H3A H -0.2318(3) 0.1905(4) -0.0931(2) 0.073 Uiso 1 calc R . C4A C -0.1356(3) 0.2895(4) -0.0123(2) 0.0602(8) Uani 1 d . . H4A H -0.1239(3) 0.1961(4) 0.0125(2) 0.072 Uiso 1 calc R . C5A C -0.2244(3) 0.3703(5) 0.0221(2) 0.0803(11) Uani 1 d . . H5A1 H -0.2012(3) 0.3904(5) 0.0705(2) 0.120 Uiso 1 calc R . H5A2 H -0.2887(3) 0.3110(5) 0.0201(2) 0.120 Uiso 1 calc R . H5A3 H -0.2397(3) 0.4608(5) -0.0023(2) 0.120 Uiso 1 calc R . C6A C 0.0591(3) 0.3067(4) 0.0171(2) 0.0587(8) Uani 1 d . . C7A C 0.2461(3) 0.3528(5) 0.0519(2) 0.0705(9) Uani 1 d . . H7A1 H 0.2414(3) 0.2494(5) 0.0630(2) 0.085 Uiso 1 calc R . H7A2 H 0.2681(3) 0.4048(5) 0.0951(2) 0.085 Uiso 1 calc R . C8A C 0.3284(3) 0.3752(4) -0.0002(2) 0.0677(9) Uani 1 d . . C9A C 0.4086(3) 0.4799(5) 0.0120(3) 0.0880(13) Uani 1 d . . H9A H 0.4091(3) 0.5374(5) 0.0524(3) 0.106 Uiso 1 calc R . C10A C 0.4881(4) 0.5007(7) -0.0346(4) 0.112(2) Uani 1 d . . H10A H 0.5414(4) 0.5717(7) -0.0259(4) 0.135 Uiso 1 calc R . C11A C 0.4870(5) 0.4155(9) -0.0936(4) 0.122(2) Uani 1 d . . H11A H 0.5412(5) 0.4265(9) -0.1246(4) 0.147 Uiso 1 calc R . C12A C 0.4065(5) 0.3133(7) -0.1077(3) 0.114(2) Uani 1 d . . H12A H 0.4051(5) 0.2577(7) -0.1488(3) 0.137 Uiso 1 calc R . C13A C 0.3279(4) 0.2935(6) -0.0609(3) 0.0926(13) Uani 1 d . . H13A H 0.2738(4) 0.2239(6) -0.0705(3) 0.111 Uiso 1 calc R . O4A O -0.1107(2) 0.0630(3) -0.1698(2) 0.0820(8) Uani 1 d . . C14A C -0.0291(4) -0.0196(6) -0.1928(3) 0.0925(13) Uani 1 d . . O5A O 0.0603(4) 0.0229(6) -0.1882(3) 0.166(2) Uani 1 d . . C15A C -0.0705(5) -0.1618(6) -0.2212(3) 0.118(2) Uani 1 d . . H15A H -0.1477(5) -0.1662(6) -0.2184(3) 0.176 Uiso 0.50 calc PR . H15B H -0.0366(5) -0.2402(6) -0.1940(3) 0.176 Uiso 0.50 calc PR . H15C H -0.0539(5) -0.1711(6) -0.2695(3) 0.176 Uiso 0.50 calc PR . H15D H -0.0111(5) -0.2188(6) -0.2362(3) 0.176 Uiso 0.50 calc PR . H15E H -0.1222(5) -0.1448(6) -0.2606(3) 0.176 Uiso 0.50 calc PR . H15F H -0.1049(5) -0.2139(6) -0.1851(3) 0.176 Uiso 0.50 calc PR . C16A C -0.0659(4) 0.3710(8) -0.2481(2) 0.104(2) Uani 1 d . . H16A H -0.1102(4) 0.4510(8) -0.2677(2) 0.125 Uiso 1 calc R . H16B H -0.0727(4) 0.2903(8) -0.2814(2) 0.125 Uiso 1 calc R . C17A C 0.0499(3) 0.4196(5) -0.2410(2) 0.0791(11) Uani 1 d . . C18A C 0.0890(4) 0.5124(6) -0.1868(3) 0.0925(13) Uani 1 d . . H18A H 0.0431(4) 0.5414(6) -0.1528(3) 0.111 Uiso 1 calc R . C19A C 0.1938(4) 0.5614(6) -0.1830(3) 0.106(2) Uani 1 d . . H19A H 0.2189(4) 0.6219(6) -0.1459(3) 0.127 Uiso 1 calc R . C20A C 0.2616(4) 0.5224(7) -0.2329(3) 0.106(2) Uani 1 d . . H20A H 0.3313(4) 0.5611(7) -0.2320(3) 0.127 Uiso 1 calc R . C21A C 0.2266(5) 0.4263(8) -0.2842(3) 0.116(2) Uani 1 d . . H21A H 0.2744(5) 0.3947(8) -0.3166(3) 0.139 Uiso 1 calc R . C22A C 0.1222(4) 0.3752(7) -0.2891(2) 0.106(2) Uani 1 d . . H22A H 0.0996(4) 0.3102(7) -0.3250(2) 0.127 Uiso 1 calc R . O1B O -0.2452(3) 0.8360(4) -0.3689(2) 0.0948(9) Uani 1 d . . N1B N -0.3553(3) 0.6570(4) -0.3228(2) 0.0790(9) Uani 1 d . . C1B C -0.2932(3) 0.7186(5) -0.3699(2) 0.0724(10) Uani 1 d . . N2B N -0.4578(2) 0.6952(3) -0.4966(2) 0.0643(7) Uani 1 d . . H2NB H -0.4571(2) 0.7877(3) -0.4882(2) 0.077 Uiso 1 calc R . C2B C -0.3827(3) 0.5292(4) -0.3654(2) 0.0691(9) Uani 1 d . . H2B H -0.4593(3) 0.5249(4) -0.3828(2) 0.083 Uiso 1 calc R . O2B O -0.5644(3) 0.4985(3) -0.5202(2) 0.1110(12) Uani 1 d . . O3B O -0.6358(2) 0.7229(3) -0.5121(2) 0.0878(9) Uani 1 d . . C3B C -0.3084(3) 0.5891(4) -0.4196(2) 0.0647(9) Uani 1 d . . H3B H -0.2415(3) 0.5313(4) -0.4194(2) 0.078 Uiso 1 calc R . C4B C -0.3556(3) 0.6162(4) -0.4952(2) 0.0666(9) Uani 1 d . . H4B H -0.3692(3) 0.5210(4) -0.5180(2) 0.080 Uiso 1 calc R . C5B C -0.2742(4) 0.7004(5) -0.5372(2) 0.0871(12) Uani 1 d . . H5B1 H -0.3050(4) 0.7165(5) -0.5845(2) 0.131 Uiso 1 calc R . H5B2 H -0.2087(4) 0.6443(5) -0.5386(2) 0.131 Uiso 1 calc R . H5B3 H -0.2580(4) 0.7929(5) -0.5149(2) 0.131 Uiso 1 calc R . C6B C -0.5519(3) 0.6284(4) -0.5106(2) 0.0716(10) Uani 1 d . . C7B C -0.7421(4) 0.6637(6) -0.5319(4) 0.134(2) Uani 1 d . . H7B1 H -0.7432(4) 0.5601(6) -0.5208(4) 0.161 Uiso 1 calc R . H7B2 H -0.7583(4) 0.6747(6) -0.5824(4) 0.161 Uiso 1 calc R . C8B C -0.8248(3) 0.7399(5) -0.4942(2) 0.0835(12) Uani 1 d . . C9B C -0.9054(4) 0.8182(6) -0.5304(3) 0.0974(14) Uani 1 d . . H9B H -0.9064(4) 0.8229(6) -0.5794(3) 0.117 Uiso 1 calc R . C10B C -0.9852(5) 0.8906(10) -0.4969(6) 0.150(3) Uani 1 d U . H10B H -1.0387(5) 0.9457(10) -0.5216(6) 0.180 Uiso 1 calc R . C11B C -0.9806(8) 0.8762(15) -0.4250(7) 0.195(4) Uani 1 d U . H11B H -1.0322(8) 0.9232(15) -0.3999(7) 0.234 Uiso 1 calc R . C12B C -0.9025(9) 0.7950(18) -0.3896(5) 0.214(5) Uani 1 d U . H12B H -0.9046(9) 0.7804(18) -0.3413(5) 0.257 Uiso 1 calc R . C13B C -0.8245(6) 0.7373(12) -0.4229(4) 0.166(3) Uani 1 d U . H13B H -0.7667(6) 0.6929(12) -0.3969(4) 0.199 Uiso 1 calc R . O4B O -0.3424(2) 0.3947(3) -0.33392(15) 0.0776(7) Uani 1 d . . C14B C -0.4153(4) 0.3142(6) -0.3000(3) 0.0926(13) Uani 1 d . . C15B C -0.3663(5) 0.1707(6) -0.2754(3) 0.114(2) Uani 1 d . . H15G H -0.2924(5) 0.1660(6) -0.2876(3) 0.171 Uiso 1 calc R . H15H H -0.4068(5) 0.0917(6) -0.2979(3) 0.171 Uiso 1 calc R . H15I H -0.3685(5) 0.1629(6) -0.2252(3) 0.171 Uiso 1 calc R . O5B O -0.5030(4) 0.3541(6) -0.2935(3) 0.176(2) Uani 1 d . . C16B C -0.3848(4) 0.7041(6) -0.2541(2) 0.102(2) Uani 1 d . . H16C H -0.3252(4) 0.7615(6) -0.2324(2) 0.123 Uiso 1 calc R . H16D H -0.3921(4) 0.6178(6) -0.2251(2) 0.123 Uiso 1 calc R . C17B C -0.4852(3) 0.7914(4) -0.2523(2) 0.0698(9) Uani 1 d . . C18B C -0.5208(4) 0.8276(5) -0.1870(2) 0.0888(13) Uani 1 d . . H18B H -0.4834(4) 0.7940(5) -0.1458(2) 0.107 Uiso 1 calc R . C19B C -0.6112(6) 0.9131(8) -0.1834(4) 0.121(2) Uani 1 d . . H19B H -0.6339(6) 0.9368(8) -0.1393(4) 0.145 Uiso 1 calc R . C20B C -0.6685(5) 0.9639(8) -0.2411(5) 0.127(2) Uani 1 d . . H20B H -0.7300(5) 1.0211(8) -0.2372(5) 0.153 Uiso 1 calc R . C21B C -0.6338(5) 0.9292(7) -0.3061(3) 0.112(2) Uani 1 d . . H21B H -0.6724(5) 0.9630(7) -0.3468(3) 0.134 Uiso 1 calc R . C22B C -0.5427(4) 0.8453(5) -0.3116(2) 0.0869(12) Uani 1 d . . H22B H -0.5196(4) 0.8244(5) -0.3559(2) 0.104 Uiso 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 O1A 0.091(2) 0.084(2) 0.114(2) 0.022(2) -0.021(2) 0.018(2) N1A 0.071(2) 0.090(3) 0.080(2) 0.017(2) 0.008(2) -0.006(2) C1A 0.059(2) 0.073(3) 0.084(2) 0.011(2) -0.009(2) -0.003(2) N2A 0.057(2) 0.0369(14) 0.084(2) -0.0007(13) -0.0013(13) 0.0000(12) C2A 0.062(2) 0.070(3) 0.075(2) -0.001(2) -0.0006(15) 0.002(2) O2A 0.078(2) 0.0324(15) 0.131(2) 0.0065(14) -0.0188(15) 0.0009(11) O3A 0.0615(13) 0.0440(13) 0.103(2) 0.0044(12) -0.0135(12) -0.0016(11) C3A 0.055(2) 0.051(2) 0.077(2) -0.002(2) 0.0023(15) -0.001(2) C4A 0.054(2) 0.051(2) 0.075(2) 0.001(2) 0.0041(14) -0.0036(14) C5A 0.068(2) 0.076(3) 0.099(3) -0.009(2) 0.023(2) 0.004(2) C6A 0.056(2) 0.045(2) 0.074(2) -0.004(2) -0.0039(14) -0.0023(15) C7A 0.062(2) 0.059(2) 0.088(2) 0.003(2) -0.011(2) 0.000(2) C8A 0.060(2) 0.052(2) 0.089(2) 0.005(2) -0.009(2) 0.004(2) C9A 0.071(3) 0.079(3) 0.112(3) 0.009(3) -0.008(2) -0.014(2) C10A 0.081(3) 0.105(4) 0.150(5) 0.023(4) 0.002(3) -0.017(3) C11A 0.099(4) 0.133(5) 0.139(5) 0.052(5) 0.028(4) 0.017(4) C12A 0.138(5) 0.109(4) 0.098(3) 0.007(3) 0.023(3) 0.014(4) C13A 0.104(3) 0.072(3) 0.102(3) -0.007(2) 0.006(3) 0.000(2) O4A 0.073(2) 0.087(2) 0.085(2) -0.0217(15) 0.0007(13) 0.0054(14) C14A 0.083(3) 0.098(4) 0.098(3) 0.000(3) 0.016(2) 0.022(3) O5A 0.094(3) 0.136(4) 0.273(6) -0.056(4) 0.050(3) 0.017(3) C15A 0.145(5) 0.095(4) 0.112(4) -0.037(3) 0.000(3) 0.015(4) C16A 0.091(3) 0.144(5) 0.077(2) 0.026(3) 0.003(2) -0.029(3) C17A 0.077(2) 0.088(3) 0.072(2) 0.014(2) 0.008(2) -0.007(2) C18A 0.091(3) 0.089(3) 0.099(3) -0.004(3) 0.017(2) -0.007(3) C19A 0.107(4) 0.096(4) 0.114(4) -0.017(3) 0.007(3) -0.026(3) C20A 0.082(3) 0.116(4) 0.120(4) 0.007(4) 0.014(3) -0.018(3) C21A 0.094(3) 0.150(5) 0.106(4) -0.011(4) 0.028(3) 0.001(4) C22A 0.108(4) 0.132(4) 0.080(3) -0.016(3) 0.022(2) -0.019(3) O1B 0.102(2) 0.071(2) 0.107(2) 0.000(2) -0.018(2) -0.011(2) N1B 0.085(2) 0.071(2) 0.081(2) -0.005(2) 0.009(2) 0.017(2) C1B 0.069(2) 0.062(3) 0.085(2) 0.000(2) -0.006(2) 0.007(2) N2B 0.064(2) 0.040(2) 0.088(2) 0.0003(14) -0.0031(14) 0.0036(13) C2B 0.068(2) 0.059(2) 0.081(2) 0.007(2) 0.003(2) 0.010(2) O2B 0.090(2) 0.043(2) 0.195(4) -0.012(2) -0.017(2) -0.0027(14) O3B 0.0624(15) 0.050(2) 0.147(2) -0.013(2) -0.0140(15) 0.0057(12) C3B 0.057(2) 0.054(2) 0.084(2) 0.006(2) 0.005(2) 0.008(2) C4B 0.065(2) 0.051(2) 0.084(2) -0.005(2) 0.008(2) 0.006(2) C5B 0.089(3) 0.082(3) 0.093(3) 0.008(2) 0.023(2) -0.001(2) C6B 0.065(2) 0.044(2) 0.103(3) 0.000(2) -0.006(2) 0.003(2) C7B 0.066(3) 0.094(4) 0.238(7) -0.059(5) -0.021(3) -0.005(3) C8B 0.061(2) 0.077(3) 0.110(3) 0.026(2) -0.008(2) -0.011(2) C9B 0.077(3) 0.104(4) 0.109(3) 0.014(3) -0.010(2) -0.002(3) C10B 0.080(3) 0.159(6) 0.208(6) 0.006(6) -0.011(4) 0.015(4) C11B 0.114(5) 0.254(10) 0.223(8) -0.024(8) 0.048(6) 0.015(6) C12B 0.174(7) 0.324(11) 0.152(6) 0.010(7) 0.060(6) -0.002(8) C13B 0.131(5) 0.237(8) 0.128(5) 0.053(6) -0.007(4) -0.002(6) O4B 0.0708(15) 0.065(2) 0.096(2) 0.0194(14) 0.0005(13) 0.0057(13) C14B 0.085(3) 0.086(3) 0.107(3) 0.021(3) 0.007(2) -0.009(3) C15B 0.126(4) 0.082(4) 0.131(4) 0.041(3) -0.012(3) -0.010(3) O5B 0.105(3) 0.165(4) 0.267(6) 0.109(5) 0.077(3) 0.032(3) C16B 0.125(4) 0.113(4) 0.068(2) 0.000(2) 0.004(2) 0.045(3) C17B 0.081(2) 0.059(2) 0.071(2) -0.001(2) 0.011(2) -0.002(2) C18B 0.110(3) 0.086(3) 0.073(2) -0.006(2) 0.024(2) -0.018(3) C19B 0.128(5) 0.119(5) 0.124(4) -0.019(4) 0.061(4) 0.002(4) C20B 0.102(4) 0.115(5) 0.170(6) -0.008(5) 0.039(4) 0.028(4) C21B 0.104(4) 0.108(4) 0.125(4) 0.017(3) 0.017(3) 0.034(3) C22B 0.096(3) 0.086(3) 0.080(2) 0.010(2) 0.010(2) 0.028(3) _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 O1A C1A 1.216(5) . ? N1A C1A 1.360(5) . ? N1A C2A 1.447(5) . ? N1A C16A 1.453(5) . ? C1A C3A 1.523(5) . ? N2A C6A 1.332(4) . ? N2A C4A 1.456(4) . ? N2A H2NA 0.86 . ? C2A O4A 1.449(5) . ? C2A C3A 1.514(5) . ? C2A H2A 0.98 . ? O2A C6A 1.204(4) . ? O3A C6A 1.353(4) . ? O3A C7A 1.448(4) . ? C3A C4A 1.518(5) . ? C3A H3A 0.98 . ? C4A C5A 1.512(5) . ? C4A H4A 0.98 . ? C5A H5A1 0.96 . ? C5A H5A2 0.96 . ? C5A H5A3 0.96 . ? C7A C8A 1.486(5) . ? C7A H7A1 0.97 . ? C7A H7A2 0.97 . ? C8A C13A 1.374(6) . ? C8A C9A 1.384(5) . ? C9A C10A 1.384(7) . ? C9A H9A 0.93 . ? C10A C11A 1.363(9) . ? C10A H10A 0.93 . ? C11A C12A 1.376(9) . ? C11A H11A 0.93 . ? C12A C13A 1.377(7) . ? C12A H12A 0.93 . ? C13A H13A 0.93 . ? O4A C14A 1.357(5) . ? C14A O5A 1.168(6) . ? C14A C15A 1.482(8) . ? C15A H15A 0.96 . ? C15A H15B 0.96 . ? C15A H15C 0.96 . ? C15A H15D 0.96 . ? C15A H15E 0.96 . ? C15A H15F 0.96 . ? C16A C17A 1.495(6) . ? C16A H16A 0.97 . ? C16A H16B 0.97 . ? C17A C22A 1.386(6) . ? C17A C18A 1.391(6) . ? C18A C19A 1.368(7) . ? C18A H18A 0.93 . ? C19A C20A 1.360(7) . ? C19A H19A 0.93 . ? C20A C21A 1.358(8) . ? C20A H20A 0.93 . ? C21A C22A 1.368(7) . ? C21A H21A 0.93 . ? C22A H22A 0.93 . ? O1B C1B 1.224(5) . ? N1B C1B 1.346(5) . ? N1B C16B 1.446(5) . ? N1B C2B 1.447(5) . ? C1B C3B 1.517(6) . ? N2B C6B 1.322(4) . ? N2B C4B 1.453(4) . ? N2B H2NB 0.86 . ? C2B O4B 1.439(5) . ? C2B C3B 1.531(5) . ? C2B H2B 0.98 . ? O2B C6B 1.209(5) . ? O3B C6B 1.348(4) . ? O3B C7B 1.444(5) . ? C3B C4B 1.530(5) . ? C3B H3B 0.98 . ? C4B C5B 1.536(5) . ? C4B H4B 0.98 . ? C5B H5B1 0.96 . ? C5B H5B2 0.96 . ? C5B H5B3 0.96 . ? C7B C8B 1.467(7) . ? C7B H7B1 0.97 . ? C7B H7B2 0.97 . ? C8B C13B 1.354(8) . ? C8B C9B 1.370(6) . ? C9B C10B 1.382(9) . ? C9B H9B 0.93 . ? C10B C11B 1.369(13) . ? C10B H10B 0.93 . ? C11B C12B 1.355(14) . ? C11B H11B 0.93 . ? C12B C13B 1.303(12) . ? C12B H12B 0.93 . ? C13B H13B 0.93 . ? O4B C14B 1.362(5) . ? C14B O5B 1.159(6) . ? C14B C15B 1.503(7) . ? C15B H15G 0.96 . ? C15B H15H 0.96 . ? C15B H15I 0.96 . ? C16B C17B 1.477(6) . ? C16B H16C 0.97 . ? C16B H16D 0.97 . ? C17B C22B 1.378(6) . ? C17B C18B 1.388(5) . ? C18B C19B 1.369(8) . ? C18B H18B 0.93 . ? C19B C20B 1.343(9) . ? C19B H19B 0.93 . ? C20B C21B 1.376(8) . ? C20B H20B 0.93 . ? C21B C22B 1.372(7) . ? C21B H21B 0.93 . ? C22B H22B 0.93 . ? 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 C1A N1A C2A 94.2(3) . . ? C1A N1A C16A 133.4(4) . . ? C2A N1A C16A 132.4(4) . . ? O1A C1A N1A 130.5(4) . . ? O1A C1A C3A 137.7(4) . . ? N1A C1A C3A 91.7(3) . . ? C6A N2A C4A 121.6(3) . . ? C6A N2A H2NA 119.2(2) . . ? C4A N2A H2NA 119.2(2) . . ? N1A C2A O4A 112.1(3) . . ? N1A C2A C3A 88.8(3) . . ? O4A C2A C3A 112.8(3) . . ? N1A C2A H2A 113.6(2) . . ? O4A C2A H2A 113.6(2) . . ? C3A C2A H2A 113.6(2) . . ? C6A O3A C7A 117.4(3) . . ? C2A C3A C4A 119.1(3) . . ? C2A C3A C1A 85.3(3) . . ? C4A C3A C1A 118.3(3) . . ? C2A C3A H3A 110.6(2) . . ? C4A C3A H3A 110.6(2) . . ? C1A C3A H3A 110.6(2) . . ? N2A C4A C5A 110.7(3) . . ? N2A C4A C3A 111.6(3) . . ? C5A C4A C3A 111.6(3) . . ? N2A C4A H4A 107.5(2) . . ? C5A C4A H4A 107.5(2) . . ? C3A C4A H4A 107.5(2) . . ? C4A C5A H5A1 109.5(2) . . ? C4A C5A H5A2 109.5(2) . . ? H5A1 C5A H5A2 109.5 . . ? C4A C5A H5A3 109.5(2) . . ? H5A1 C5A H5A3 109.5 . . ? H5A2 C5A H5A3 109.5 . . ? O2A C6A N2A 126.0(3) . . ? O2A C6A O3A 122.9(3) . . ? N2A C6A O3A 111.1(3) . . ? O3A C7A C8A 110.7(3) . . ? O3A C7A H7A1 109.5(2) . . ? C8A C7A H7A1 109.5(2) . . ? O3A C7A H7A2 109.5(2) . . ? C8A C7A H7A2 109.5(2) . . ? H7A1 C7A H7A2 108.1 . . ? C13A C8A C9A 118.3(4) . . ? C13A C8A C7A 121.6(4) . . ? C9A C8A C7A 120.0(4) . . ? C8A C9A C10A 121.4(5) . . ? C8A C9A H9A 119.3(3) . . ? C10A C9A H9A 119.3(3) . . ? C11A C10A C9A 118.9(5) . . ? C11A C10A H10A 120.5(4) . . ? C9A C10A H10A 120.5(3) . . ? C10A C11A C12A 120.7(6) . . ? C10A C11A H11A 119.7(4) . . ? C12A C11A H11A 119.7(4) . . ? C11A C12A C13A 119.8(6) . . ? C11A C12A H12A 120.1(4) . . ? C13A C12A H12A 120.1(4) . . ? C8A C13A C12A 120.8(5) . . ? C8A C13A H13A 119.6(3) . . ? C12A C13A H13A 119.6(4) . . ? C14A O4A C2A 117.9(4) . . ? O5A C14A O4A 120.8(5) . . ? O5A C14A C15A 128.1(5) . . ? O4A C14A C15A 111.1(5) . . ? C14A C15A H15A 109.5(3) . . ? C14A C15A H15B 109.5(3) . . ? H15A C15A H15B 109.5 . . ? C14A C15A H15C 109.5(3) . . ? H15A C15A H15C 109.5 . . ? H15B C15A H15C 109.5 . . ? C14A C15A H15D 109.5(3) . . ? H15A C15A H15D 141.1 . . ? H15B C15A H15D 56.3 . . ? H15C C15A H15D 56.3 . . ? C14A C15A H15E 109.5(3) . . ? H15A C15A H15E 56.3 . . ? H15B C15A H15E 141.1 . . ? H15C C15A H15E 56.3 . . ? H15D C15A H15E 109.5 . . ? C14A C15A H15F 109.5(3) . . ? H15A C15A H15F 56.3 . . ? H15B C15A H15F 56.3 . . ? H15C C15A H15F 141.1 . . ? H15D C15A H15F 109.5 . . ? H15E C15A H15F 109.5 . . ? N1A C16A C17A 114.2(4) . . ? N1A C16A H16A 108.7(3) . . ? C17A C16A H16A 108.7(3) . . ? N1A C16A H16B 108.7(3) . . ? C17A C16A H16B 108.7(3) . . ? H16A C16A H16B 107.6 . . ? C22A C17A C18A 117.5(4) . . ? C22A C17A C16A 120.8(4) . . ? C18A C17A C16A 121.7(4) . . ? C19A C18A C17A 120.9(5) . . ? C19A C18A H18A 119.5(3) . . ? C17A C18A H18A 119.5(3) . . ? C20A C19A C18A 120.5(5) . . ? C20A C19A H19A 119.8(3) . . ? C18A C19A H19A 119.8(3) . . ? C21A C20A C19A 119.4(5) . . ? C21A C20A H20A 120.3(3) . . ? C19A C20A H20A 120.3(3) . . ? C20A C21A C22A 121.2(5) . . ? C20A C21A H21A 119.4(3) . . ? C22A C21A H21A 119.4(3) . . ? C21A C22A C17A 120.4(5) . . ? C21A C22A H22A 119.8(3) . . ? C17A C22A H22A 119.8(3) . . ? C1B N1B C16B 132.1(4) . . ? C1B N1B C2B 94.9(3) . . ? C16B N1B C2B 132.9(4) . . ? O1B C1B N1B 130.9(4) . . ? O1B C1B C3B 136.9(4) . . ? N1B C1B C3B 92.2(3) . . ? C6B N2B C4B 121.7(3) . . ? C6B N2B H2NB 119.2(2) . . ? C4B N2B H2NB 119.2(2) . . ? O4B C2B N1B 113.3(3) . . ? O4B C2B C3B 112.2(3) . . ? N1B C2B C3B 87.8(3) . . ? O4B C2B H2B 113.7(2) . . ? N1B C2B H2B 113.7(2) . . ? C3B C2B H2B 113.7(2) . . ? C6B O3B C7B 116.7(3) . . ? C1B C3B C4B 118.6(3) . . ? C1B C3B C2B 85.0(3) . . ? C4B C3B C2B 118.9(3) . . ? C1B C3B H3B 110.7(2) . . ? C4B C3B H3B 110.7(2) . . ? C2B C3B H3B 110.7(2) . . ? N2B C4B C3B 111.6(3) . . ? N2B C4B C5B 110.1(3) . . ? C3B C4B C5B 110.5(3) . . ? N2B C4B H4B 108.2(2) . . ? C3B C4B H4B 108.2(2) . . ? C5B C4B H4B 108.2(2) . . ? C4B C5B H5B1 109.5(2) . . ? C4B C5B H5B2 109.5(2) . . ? H5B1 C5B H5B2 109.5 . . ? C4B C5B H5B3 109.5(2) . . ? H5B1 C5B H5B3 109.5 . . ? H5B2 C5B H5B3 109.5 . . ? O2B C6B N2B 125.7(4) . . ? O2B C6B O3B 122.4(4) . . ? N2B C6B O3B 111.9(3) . . ? O3B C7B C8B 110.4(4) . . ? O3B C7B H7B1 109.6(3) . . ? C8B C7B H7B1 109.6(3) . . ? O3B C7B H7B2 109.6(3) . . ? C8B C7B H7B2 109.6(3) . . ? H7B1 C7B H7B2 108.1 . . ? C13B C8B C9B 117.4(6) . . ? C13B C8B C7B 122.0(6) . . ? C9B C8B C7B 120.5(5) . . ? C8B C9B C10B 122.3(6) . . ? C8B C9B H9B 118.8(3) . . ? C10B C9B H9B 118.8(4) . . ? C11B C10B C9B 115.9(7) . . ? C11B C10B H10B 122.1(6) . . ? C9B C10B H10B 122.1(4) . . ? C12B C11B C10B 121.5(9) . . ? C12B C11B H11B 119.2(6) . . ? C10B C11B H11B 119.2(6) . . ? C13B C12B C11B 120.4(9) . . ? C13B C12B H12B 119.8(6) . . ? C11B C12B H12B 119.8(6) . . ? C12B C13B C8B 122.1(8) . . ? C12B C13B H13B 119.0(6) . . ? C8B C13B H13B 119.0(4) . . ? C14B O4B C2B 115.9(3) . . ? O5B C14B O4B 122.5(5) . . ? O5B C14B C15B 126.8(5) . . ? O4B C14B C15B 110.6(4) . . ? C14B C15B H15G 109.5(3) . . ? C14B C15B H15H 109.5(3) . . ? H15G C15B H15H 109.5 . . ? C14B C15B H15I 109.5(3) . . ? H15G C15B H15I 109.5 . . ? H15H C15B H15I 109.5 . . ? N1B C16B C17B 116.7(4) . . ? N1B C16B H16C 108.1(3) . . ? C17B C16B H16C 108.1(3) . . ? N1B C16B H16D 108.1(3) . . ? C17B C16B H16D 108.1(3) . . ? H16C C16B H16D 107.3 . . ? C22B C17B C18B 117.9(4) . . ? C22B C17B C16B 123.8(4) . . ? C18B C17B C16B 118.2(4) . . ? C19B C18B C17B 119.6(5) . . ? C19B C18B H18B 120.2(4) . . ? C17B C18B H18B 120.2(3) . . ? C20B C19B C18B 122.6(5) . . ? C20B C19B H19B 118.7(4) . . ? C18B C19B H19B 118.7(4) . . ? C19B C20B C21B 118.3(5) . . ? C19B C20B H20B 120.9(4) . . ? C21B C20B H20B 120.9(4) . . ? C22B C21B C20B 120.6(6) . . ? C22B C21B H21B 119.7(3) . . ? C20B C21B H21B 119.7(4) . . ? C21B C22B C17B 120.9(4) . . ? C21B C22B H22B 119.5(3) . . ? C17B C22B H22B 119.5(2) . . ? 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 C2A N1A C1A O1A 176.4(4) . . . . ? C16A N1A C1A O1A -2.4(8) . . . . ? C2A N1A C1A C3A -2.3(3) . . . . ? C16A N1A C1A C3A 179.0(5) . . . . ? C1A N1A C2A O4A 116.5(3) . . . . ? C16A N1A C2A O4A -64.8(5) . . . . ? C1A N1A C2A C3A 2.3(3) . . . . ? C16A N1A C2A C3A -178.9(4) . . . . ? N1A C2A C3A C4A -122.0(3) . . . . ? O4A C2A C3A C4A 124.5(3) . . . . ? N1A C2A C3A C1A -2.0(3) . . . . ? O4A C2A C3A C1A -115.6(3) . . . . ? O1A C1A C3A C2A -176.3(5) . . . . ? N1A C1A C3A C2A 2.2(3) . . . . ? O1A C1A C3A C4A -55.6(6) . . . . ? N1A C1A C3A C4A 122.8(3) . . . . ? C6A N2A C4A C5A 132.2(3) . . . . ? C6A N2A C4A C3A -102.7(4) . . . . ? C2A C3A C4A N2A 43.6(4) . . . . ? C1A C3A C4A N2A -57.5(4) . . . . ? C2A C3A C4A C5A 168.1(3) . . . . ? C1A C3A C4A C5A 67.0(4) . . . . ? C4A N2A C6A O2A 4.0(6) . . . . ? C4A N2A C6A O3A -176.4(3) . . . . ? C7A O3A C6A O2A -4.3(5) . . . . ? C7A O3A C6A N2A 176.1(3) . . . . ? C6A O3A C7A C8A 119.3(4) . . . . ? O3A C7A C8A C13A -71.1(5) . . . . ? O3A C7A C8A C9A 109.4(4) . . . . ? C13A C8A C9A C10A -1.2(6) . . . . ? C7A C8A C9A C10A 178.3(4) . . . . ? C8A C9A C10A C11A -0.3(8) . . . . ? C9A C10A C11A C12A 1.9(9) . . . . ? C10A C11A C12A C13A -2.0(9) . . . . ? C9A C8A C13A C12A 1.2(7) . . . . ? C7A C8A C13A C12A -178.3(4) . . . . ? C11A C12A C13A C8A 0.4(8) . . . . ? N1A C2A O4A C14A 103.5(4) . . . . ? C3A C2A O4A C14A -158.1(4) . . . . ? C2A O4A C14A O5A -3.1(7) . . . . ? C2A O4A C14A C15A 175.9(4) . . . . ? C1A N1A C16A C17A 111.2(6) . . . . ? C2A N1A C16A C17A -67.1(7) . . . . ? N1A C16A C17A C22A 135.9(5) . . . . ? N1A C16A C17A C18A -45.1(7) . . . . ? C22A C17A C18A C19A 2.2(8) . . . . ? C16A C17A C18A C19A -176.9(5) . . . . ? C17A C18A C19A C20A 1.2(8) . . . . ? C18A C19A C20A C21A -4.3(9) . . . . ? C19A C20A C21A C22A 4.1(10) . . . . ? C20A C21A C22A C17A -0.7(10) . . . . ? C18A C17A C22A C21A -2.4(8) . . . . ? C16A C17A C22A C21A 176.6(5) . . . . ? C16B N1B C1B O1B -2.2(7) . . . . ? C2B N1B C1B O1B 177.1(4) . . . . ? C16B N1B C1B C3B 177.8(4) . . . . ? C2B N1B C1B C3B -2.9(3) . . . . ? C1B N1B C2B O4B 116.1(3) . . . . ? C16B N1B C2B O4B -64.6(5) . . . . ? C1B N1B C2B C3B 2.8(3) . . . . ? C16B N1B C2B C3B -177.9(4) . . . . ? O1B C1B C3B C4B -57.0(6) . . . . ? N1B C1B C3B C4B 123.0(3) . . . . ? O1B C1B C3B C2B -177.3(5) . . . . ? N1B C1B C3B C2B 2.7(3) . . . . ? O4B C2B C3B C1B -116.9(3) . . . . ? N1B C2B C3B C1B -2.5(3) . . . . ? O4B C2B C3B C4B 123.1(3) . . . . ? N1B C2B C3B C4B -122.6(3) . . . . ? C6B N2B C4B C3B -103.8(4) . . . . ? C6B N2B C4B C5B 133.1(4) . . . . ? C1B C3B C4B N2B -53.6(4) . . . . ? C2B C3B C4B N2B 47.2(4) . . . . ? C1B C3B C4B C5B 69.3(4) . . . . ? C2B C3B C4B C5B 170.1(3) . . . . ? C4B N2B C6B O2B 3.6(7) . . . . ? C4B N2B C6B O3B -177.5(4) . . . . ? C7B O3B C6B O2B -5.4(7) . . . . ? C7B O3B C6B N2B 175.7(4) . . . . ? C6B O3B C7B C8B 146.7(4) . . . . ? O3B C7B C8B C13B -61.9(8) . . . . ? O3B C7B C8B C9B 117.4(6) . . . . ? C13B C8B C9B C10B -1.1(9) . . . . ? C7B C8B C9B C10B 179.5(6) . . . . ? C8B C9B C10B C11B -1.6(11) . . . . ? C9B C10B C11B C12B -0.4(16) . . . . ? C10B C11B C12B C13B 5.2(20) . . . . ? C11B C12B C13B C8B -8.3(19) . . . . ? C9B C8B C13B C12B 6.2(13) . . . . ? C7B C8B C13B C12B -174.4(9) . . . . ? N1B C2B O4B C14B 99.2(4) . . . . ? C3B C2B O4B C14B -163.2(4) . . . . ? C2B O4B C14B O5B -3.8(8) . . . . ? C2B O4B C14B C15B 174.7(4) . . . . ? C1B N1B C16B C17B 90.9(6) . . . . ? C2B N1B C16B C17B -88.2(6) . . . . ? N1B C16B C17B C22B -8.8(8) . . . . ? N1B C16B C17B C18B 174.6(4) . . . . ? C22B C17B C18B C19B 0.7(7) . . . . ? C16B C17B C18B C19B 177.5(5) . . . . ? C17B C18B C19B C20B 0.3(9) . . . . ? C18B C19B C20B C21B -0.6(11) . . . . ? C19B C20B C21B C22B -0.2(10) . . . . ? C20B C21B C22B C17B 1.3(9) . . . . ? C18B C17B C22B C21B -1.5(7) . . . . ? C16B C17B C22B C21B -178.1(5) . . . . ? _refine_diff_density_max 0.198 _refine_diff_density_min -0.182 _refine_diff_density_rms 0.046 data_s595rm1 _database_code_CSD 165014 _publ_contact_author ' Joachim Podlech' _publ_contact_author_email joachim.podlech@po.uni-stuttgart.de loop_ _publ_author_name 'Michael R. Linder' 'Wolfgang U. Frey' 'Joachim Podlech' _journal_name_full 'Journal of the Chemical Society, Perkin Transactions 1' _journal_coden_Cambridge 207 _audit_creation_method SHELXL _chemical_name_systematic ; N-Benzyl-2,4,6-trimethoxybenzaldimine ; _chemical_name_common ? _chemical_formula_moiety ? _chemical_formula_structural ? _chemical_formula_analytical ? _chemical_formula_sum 'C17 H19 N O3' _chemical_formula_weight 285.33 _chemical_melting_point '356 - 358 K' _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' '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' _symmetry_cell_setting orthorhombic _symmetry_space_group_name_H-M Pbca 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' '-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 15.917(2) _cell_length_b 9.1897(10) _cell_length_c 20.868(3) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 3052.5(6) _cell_formula_units_Z 8 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 26 _cell_measurement_theta_min 9 _cell_measurement_theta_max 12 _exptl_crystal_description block _exptl_crystal_colour colourless _exptl_crystal_size_max 0.40 _exptl_crystal_size_mid 0.30 _exptl_crystal_size_min 0.25 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.242 _exptl_crystal_density_method ? _exptl_crystal_F_000 1216 _exptl_absorpt_coefficient_mu 0.085 _exptl_absorpt_correction_type none _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 293(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device Nicolet P3 _diffrn_measurement_method Wyckoff - scan _diffrn_standards_number 3 _diffrn_standards_interval_count 50 _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 2687 _diffrn_reflns_av_R_equivalents 0.0000 _diffrn_reflns_av_sigmaI/netI 0.0399 _diffrn_reflns_limit_h_min 0 _diffrn_reflns_limit_h_max 18 _diffrn_reflns_limit_k_min 0 _diffrn_reflns_limit_k_max 10 _diffrn_reflns_limit_l_min -24 _diffrn_reflns_limit_l_max 0 _diffrn_reflns_theta_min 1.95 _diffrn_reflns_theta_max 25.00 _reflns_number_total 2687 _reflns_number_observed 1682 _reflns_observed_criterion >2sigma(I) _computing_data_collection Siemens P3/PC Data Collection System _computing_cell_refinement Siemens P3/PC Data Collection System _computing_data_reduction SHELXTL plus - XDISK _computing_structure_solution 'SHELXS-86 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-93 (Sheldrick, 1993)' _computing_molecular_graphics SHELXTL - XP _computing_publication_material ? _refine_special_details ; Refinement on F^2^ for ALL reflections except for 311 with very negative F^2^ or flagged by the user for potential systematic errors. Weighted R-factors wR and all goodnesses 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 observed criterion of F^2^ > 2sigma(F^2^) is used only for calculating _R_factor_obs 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 w=1/[\s^2^(Fo^2^)+(0.0337P)^2^+1.7669P] 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 ? _refine_ls_extinction_method SHELXL _refine_ls_extinction_coef 0.0038(5) _refine_ls_extinction_expression 'Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^' _refine_ls_number_reflns 2376 _refine_ls_number_parameters 191 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.1065 _refine_ls_R_factor_obs 0.0620 _refine_ls_wR_factor_all 0.1406 _refine_ls_wR_factor_obs 0.1165 _refine_ls_goodness_of_fit_all 1.077 _refine_ls_goodness_of_fit_obs 1.185 _refine_ls_restrained_S_all 1.111 _refine_ls_restrained_S_obs 1.185 _refine_ls_shift/esd_max 0.000 _refine_ls_shift/esd_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_thermal_displace_type _atom_site_occupancy _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_group C1 C 0.8519(2) 0.4322(3) 0.68600(12) 0.0453(6) Uani 1 d . . C2 C 0.8116(2) 0.3630(3) 0.63438(13) 0.0507(7) Uani 1 d . . C3 C 0.8506(2) 0.2595(3) 0.59744(13) 0.0539(7) Uani 1 d . . H3 H 0.8222(2) 0.2148(3) 0.56382(13) 0.065 Uiso 1 calc R . C4 C 0.9328(2) 0.2228(3) 0.61112(13) 0.0490(7) Uani 1 d . . C5 C 0.9752(2) 0.2857(3) 0.66140(13) 0.0507(7) Uani 1 d . . H5 H 1.0302(2) 0.2588(3) 0.67047(13) 0.061 Uiso 1 calc R . C6 C 0.9348(2) 0.3902(3) 0.69853(12) 0.0474(7) Uani 1 d . . C7 C 0.8052(2) 0.5427(3) 0.72229(14) 0.0505(7) Uani 1 d . . H7 H 0.7630(2) 0.5920(3) 0.70035(14) 0.061 Uiso 1 calc R . C8 C 0.7594(2) 0.6883(3) 0.80464(14) 0.0665(9) Uani 1 d . . H8A H 0.7238(2) 0.7240(3) 0.77031(14) 0.080 Uiso 1 calc R . H8B H 0.7923(2) 0.7696(3) 0.82049(14) 0.080 Uiso 1 calc R . C9 C 0.7050(2) 0.6316(3) 0.85777(13) 0.0525(7) Uani 1 d . . C10 C 0.6276(2) 0.6924(4) 0.8691(2) 0.0913(12) Uani 1 d . . H10 H 0.6080(2) 0.7672(4) 0.8431(2) 0.110 Uiso 1 calc R . C11 C 0.5783(3) 0.6419(6) 0.9197(3) 0.133(2) Uani 1 d . . H11 H 0.5260(3) 0.6833(6) 0.9276(3) 0.159 Uiso 1 calc R . C12 C 0.6069(4) 0.5318(7) 0.9578(3) 0.127(2) Uani 1 d . . H12 H 0.5739(4) 0.4982(7) 0.9915(3) 0.153 Uiso 1 calc R . C13 C 0.6821(3) 0.4718(5) 0.9467(2) 0.1007(14) Uani 1 d . . H13 H 0.7013(3) 0.3967(5) 0.9728(2) 0.121 Uiso 1 calc R . C14 C 0.7308(2) 0.5208(4) 0.89728(15) 0.0686(9) Uani 1 d . . H14 H 0.7828(2) 0.4778(4) 0.89018(15) 0.082 Uiso 1 calc R . C15 C 0.6829(2) 0.3339(4) 0.5770(2) 0.0849(11) Uani 1 d . . H15A H 0.6272(2) 0.3735(4) 0.5757(2) 0.127 Uiso 1 calc R . H15B H 0.6801(2) 0.2317(4) 0.5862(2) 0.127 Uiso 1 calc R . H15C H 0.7096(2) 0.3481(4) 0.5362(2) 0.127 Uiso 1 calc R . C16 C 1.0526(2) 0.0822(4) 0.58053(15) 0.0670(9) Uani 1 d . . H16A H 1.0683(2) 0.0088(4) 0.55004(15) 0.100 Uiso 1 calc R . H16B H 1.0607(2) 0.0456(4) 0.62317(15) 0.100 Uiso 1 calc R . H16C H 1.0868(2) 0.1671(4) 0.57433(15) 0.100 Uiso 1 calc R . C17 C 1.0584(2) 0.4182(4) 0.7629(2) 0.0830(11) Uani 1 d . . H17A H 1.0774(2) 0.4729(4) 0.7993(2) 0.124 Uiso 1 calc R . H17B H 1.0932(2) 0.4399(4) 0.7266(2) 0.124 Uiso 1 calc R . H17C H 1.0616(2) 0.3161(4) 0.7723(2) 0.124 Uiso 1 calc R . N1 N 0.8162(2) 0.5773(3) 0.77911(12) 0.0635(7) Uani 1 d . . O1 O 0.73007(12) 0.4052(2) 0.62536(10) 0.0738(7) Uani 1 d . . O2 O 0.96650(12) 0.1193(2) 0.57169(9) 0.0659(6) Uani 1 d . . O3 O 0.97329(12) 0.4565(2) 0.74881(10) 0.0665(6) Uani 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 C1 0.049(2) 0.0425(15) 0.0445(14) 0.0045(13) 0.0076(12) 0.0027(13) C2 0.048(2) 0.054(2) 0.050(2) 0.0054(14) -0.0024(13) 0.0061(14) C3 0.058(2) 0.057(2) 0.047(2) -0.0079(14) -0.0046(14) 0.007(2) C4 0.056(2) 0.046(2) 0.046(2) -0.0034(14) 0.0051(13) 0.0040(14) C5 0.0446(15) 0.054(2) 0.054(2) -0.0031(14) -0.0002(13) 0.0075(14) C6 0.048(2) 0.049(2) 0.0450(15) -0.0060(13) 0.0037(13) -0.0019(14) C7 0.054(2) 0.044(2) 0.053(2) 0.0064(14) 0.0057(14) 0.0089(14) C8 0.080(2) 0.052(2) 0.067(2) -0.004(2) 0.021(2) 0.015(2) C9 0.055(2) 0.047(2) 0.056(2) -0.0122(14) 0.0055(14) 0.0027(14) C10 0.074(2) 0.078(3) 0.121(3) -0.002(2) 0.019(2) 0.014(2) C11 0.095(3) 0.117(4) 0.186(6) -0.020(4) 0.072(4) 0.002(3) C12 0.129(5) 0.125(5) 0.128(4) -0.012(4) 0.063(4) -0.043(4) C13 0.120(4) 0.102(3) 0.080(3) 0.019(2) 0.003(3) -0.035(3) C14 0.067(2) 0.066(2) 0.073(2) 0.004(2) -0.006(2) -0.011(2) C15 0.065(2) 0.104(3) 0.086(2) -0.020(2) -0.024(2) 0.016(2) C16 0.062(2) 0.072(2) 0.067(2) -0.016(2) 0.008(2) 0.016(2) C17 0.052(2) 0.103(3) 0.094(3) -0.038(2) -0.019(2) 0.010(2) N1 0.068(2) 0.066(2) 0.057(2) -0.0060(13) 0.0091(13) 0.0163(14) O1 0.0576(13) 0.086(2) 0.0779(14) -0.0222(13) -0.0170(11) 0.0220(12) O2 0.0630(13) 0.0698(14) 0.0649(13) -0.0235(11) -0.0034(11) 0.0162(11) O3 0.0521(12) 0.0781(14) 0.0692(12) -0.0291(12) -0.0055(11) 0.0118(11) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag C1 C6 1.399(3) . ? C1 C2 1.406(4) . ? C1 C7 1.469(4) . ? C2 O1 1.367(3) . ? C2 C3 1.373(4) . ? C3 C4 1.381(4) . ? C3 H3 0.93 . ? C4 O2 1.367(3) . ? C4 C5 1.375(4) . ? C5 C6 1.391(3) . ? C5 H5 0.93 . ? C6 O3 1.359(3) . ? C7 N1 1.240(3) . ? C7 H7 0.93 . ? C8 N1 1.464(3) . ? C8 C9 1.500(4) . ? C8 H8A 0.97 . ? C8 H8B 0.97 . ? C9 C14 1.372(4) . ? C9 C10 1.374(4) . ? C10 C11 1.395(6) . ? C10 H10 0.93 . ? C11 C12 1.364(7) . ? C11 H11 0.93 . ? C12 C13 1.338(6) . ? C12 H12 0.93 . ? C13 C14 1.366(5) . ? C13 H13 0.93 . ? C14 H14 0.93 . ? C15 O1 1.419(3) . ? C15 H15A 0.96 . ? C15 H15B 0.96 . ? C15 H15C 0.96 . ? C16 O2 1.424(3) . ? C16 H16A 0.96 . ? C16 H16B 0.96 . ? C16 H16C 0.96 . ? C17 O3 1.430(3) . ? C17 H17A 0.96 . ? C17 H17B 0.96 . ? C17 H17C 0.96 . ? 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 C6 C1 C2 116.7(2) . . ? C6 C1 C7 124.8(3) . . ? C2 C1 C7 118.5(2) . . ? O1 C2 C3 123.3(3) . . ? O1 C2 C1 114.3(2) . . ? C3 C2 C1 122.5(3) . . ? C2 C3 C4 118.8(3) . . ? C2 C3 H3 120.6(2) . . ? C4 C3 H3 120.6(2) . . ? O2 C4 C5 124.0(2) . . ? O2 C4 C3 114.6(3) . . ? C5 C4 C3 121.3(3) . . ? C4 C5 C6 119.3(2) . . ? C4 C5 H5 120.4(2) . . ? C6 C5 H5 120.4(2) . . ? O3 C6 C5 122.1(2) . . ? O3 C6 C1 116.5(2) . . ? C5 C6 C1 121.5(3) . . ? N1 C7 C1 126.8(3) . . ? N1 C7 H7 116.6(2) . . ? C1 C7 H7 116.6(2) . . ? N1 C8 C9 112.5(2) . . ? N1 C8 H8A 109.1(2) . . ? C9 C8 H8A 109.1(2) . . ? N1 C8 H8B 109.1(2) . . ? C9 C8 H8B 109.1(2) . . ? H8A C8 H8B 107.8 . . ? C14 C9 C10 117.8(3) . . ? C14 C9 C8 122.0(3) . . ? C10 C9 C8 120.2(3) . . ? C9 C10 C11 119.9(4) . . ? C9 C10 H10 120.0(2) . . ? C11 C10 H10 120.0(3) . . ? C12 C11 C10 120.0(5) . . ? C12 C11 H11 120.0(3) . . ? C10 C11 H11 120.0(3) . . ? C13 C12 C11 120.2(5) . . ? C13 C12 H12 119.9(3) . . ? C11 C12 H12 119.9(3) . . ? C12 C13 C14 120.1(4) . . ? C12 C13 H13 119.9(3) . . ? C14 C13 H13 119.9(3) . . ? C13 C14 C9 121.9(4) . . ? C13 C14 H14 119.0(3) . . ? C9 C14 H14 119.0(2) . . ? O1 C15 H15A 109.5(2) . . ? O1 C15 H15B 109.5(2) . . ? H15A C15 H15B 109.5 . . ? O1 C15 H15C 109.5(2) . . ? H15A C15 H15C 109.5 . . ? H15B C15 H15C 109.5 . . ? O2 C16 H16A 109.47(15) . . ? O2 C16 H16B 109.5(2) . . ? H16A C16 H16B 109.5 . . ? O2 C16 H16C 109.5(2) . . ? H16A C16 H16C 109.5 . . ? H16B C16 H16C 109.5 . . ? O3 C17 H17A 109.5(2) . . ? O3 C17 H17B 109.5(2) . . ? H17A C17 H17B 109.5 . . ? O3 C17 H17C 109.5(2) . . ? H17A C17 H17C 109.5 . . ? H17B C17 H17C 109.5 . . ? C7 N1 C8 116.1(3) . . ? C2 O1 C15 118.0(2) . . ? C4 O2 C16 117.8(2) . . ? C6 O3 C17 118.4(2) . . ? 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 C6 C1 C2 O1 178.3(2) . . . . ? C7 C1 C2 O1 -2.2(4) . . . . ? C6 C1 C2 C3 -0.2(4) . . . . ? C7 C1 C2 C3 179.4(3) . . . . ? O1 C2 C3 C4 -178.9(3) . . . . ? C1 C2 C3 C4 -0.6(4) . . . . ? C2 C3 C4 O2 -179.7(2) . . . . ? C2 C3 C4 C5 1.2(4) . . . . ? O2 C4 C5 C6 180.0(3) . . . . ? C3 C4 C5 C6 -1.1(4) . . . . ? C4 C5 C6 O3 -179.9(2) . . . . ? C4 C5 C6 C1 0.2(4) . . . . ? C2 C1 C6 O3 -179.5(2) . . . . ? C7 C1 C6 O3 1.0(4) . . . . ? C2 C1 C6 C5 0.4(4) . . . . ? C7 C1 C6 C5 -179.1(3) . . . . ? C6 C1 C7 N1 -27.5(4) . . . . ? C2 C1 C7 N1 153.0(3) . . . . ? N1 C8 C9 C14 29.0(4) . . . . ? N1 C8 C9 C10 -152.4(3) . . . . ? C14 C9 C10 C11 0.5(5) . . . . ? C8 C9 C10 C11 -178.2(4) . . . . ? C9 C10 C11 C12 -0.3(7) . . . . ? C10 C11 C12 C13 0.0(8) . . . . ? C11 C12 C13 C14 0.0(8) . . . . ? C12 C13 C14 C9 0.2(6) . . . . ? C10 C9 C14 C13 -0.4(5) . . . . ? C8 C9 C14 C13 178.2(3) . . . . ? C1 C7 N1 C8 -178.3(3) . . . . ? C9 C8 N1 C7 116.4(3) . . . . ? C3 C2 O1 C15 2.5(4) . . . . ? C1 C2 O1 C15 -175.9(3) . . . . ? C5 C4 O2 C16 -4.6(4) . . . . ? C3 C4 O2 C16 176.4(3) . . . . ? C5 C6 O3 C17 0.9(4) . . . . ? C1 C6 O3 C17 -179.3(3) . . . . ? _refine_diff_density_max 0.199 _refine_diff_density_min -0.136 _refine_diff_density_rms 0.031 data_s549rc2 _database_code_CSD 168278 _publ_contact_author 'Joachim Podlech' _publ_contact_author_email joachim.podlech@po.uni-stuttgart.de loop_ _publ_author_name 'Michael R. Linder' 'Wolfgang U. Frey' 'Joachim Podlech' _journal_coden_Cambridge 207 _journal_name_full 'Journal of the Chemical Society, Perkin Transactions 1' _audit_creation_method SHELXL _chemical_name_systematic ; (3S,4R,1'S)-1-Benzyl-3-[1-(benzyloxycarbonylamino)ethyl]-4-(2-thienyl)- azetidin-2-one ; _chemical_name_common ? _chemical_formula_moiety ? _chemical_formula_structural ? _chemical_formula_analytical ? _chemical_formula_sum 'C24 H24 N2 O3 S' _chemical_formula_weight 420.51 _chemical_melting_point '378 - 379 K' _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' 0.0181 0.0091 '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' 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 'O' 'O' 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 'S' 'S' 0.3331 0.5567 '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) loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z' _cell_length_a 9.2101(5) _cell_length_b 20.7429(10) _cell_length_c 11.5524(6) _cell_angle_alpha 90.00 _cell_angle_beta 90.117(5) _cell_angle_gamma 90.00 _cell_volume 2207.0(2) _cell_formula_units_Z 4 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 50 _cell_measurement_theta_min 22.5 _cell_measurement_theta_max 50 _exptl_crystal_description plates _exptl_crystal_colour colourless _exptl_crystal_size_max 0.40 _exptl_crystal_size_mid 0.15 _exptl_crystal_size_min 0.15 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.266 _exptl_crystal_density_method ? _exptl_crystal_F_000 888 _exptl_absorpt_coefficient_mu 1.523 _exptl_absorpt_correction_type Psi- Scan _exptl_absorpt_correction_T_min 0.526 _exptl_absorpt_correction_T_max 1.0 _exptl_special_details ; ? ; _diffrn_ambient_temperature 293(2) _diffrn_radiation_wavelength 1.54178 _diffrn_radiation_type CuK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device Siemens P4 _diffrn_measurement_method Omega Scan _diffrn_standards_number 3 _diffrn_standards_interval_count 100 _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 7539 _diffrn_reflns_av_R_equivalents 0.0388 _diffrn_reflns_av_sigmaI/netI 0.0375 _diffrn_reflns_limit_h_min -11 _diffrn_reflns_limit_h_max 10 _diffrn_reflns_limit_k_min -24 _diffrn_reflns_limit_k_max 24 _diffrn_reflns_limit_l_min -13 _diffrn_reflns_limit_l_max 13 _diffrn_reflns_theta_min 3.83 _diffrn_reflns_theta_max 68.00 _reflns_number_total 6870 _reflns_number_observed 5301 _reflns_observed_criterion >2sigma(I) _computing_data_collection Siemens XSCANS _computing_cell_refinement SIEMENS XSCANS _computing_data_reduction Siemens XSCANS and XEMP _computing_structure_solution 'SHELXS-86 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-93 (Sheldrick, 1993)' _computing_molecular_graphics SHELXTL - XP _computing_publication_material ? _refine_special_details ; Refinement on F^2^ for ALL reflections except for 210 with very negative F^2^ or flagged by the user for potential systematic errors. Weighted R-factors wR and all goodnesses 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 observed criterion of F^2^ > 2sigma(F^2^) is used only for calculating _R_factor_obs 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 w=1/[\s^2^(Fo^2^)+(0.1483P)^2^+0.5129P] 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 ? _refine_ls_extinction_method SHELXL _refine_ls_extinction_coef 0.0075(3) _refine_ls_extinction_expression 'Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^' _refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _refine_ls_abs_structure_Flack 0.05(4) _refine_ls_number_reflns 6660 _refine_ls_number_parameters 616 _refine_ls_number_restraints 317 _refine_ls_R_factor_all 0.0944 _refine_ls_R_factor_obs 0.0790 _refine_ls_wR_factor_all 0.2715 _refine_ls_wR_factor_obs 0.2244 _refine_ls_goodness_of_fit_all 1.169 _refine_ls_goodness_of_fit_obs 1.206 _refine_ls_restrained_S_all 1.263 _refine_ls_restrained_S_obs 1.192 _refine_ls_shift/esd_max -0.033 _refine_ls_shift/esd_mean 0.001 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_thermal_displace_type _atom_site_occupancy _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_group N1A N 0.8360(2) 0.32185(8) 0.34684(15) 0.0713(5) Uani 1 d . . O1A O 1.0367(2) 0.33680(8) 0.46688(13) 0.0860(5) Uani 1 d . . C1A C 0.9426(2) 0.30421(10) 0.4213(2) 0.0653(6) Uani 1 d . . N2A N 0.7679(2) 0.24932(8) 0.60906(13) 0.0631(4) Uani 1 d . . H2A H 0.6779 0.25633 0.59328 0.076 Uiso 1 calc R . O2A O 0.95584(14) 0.27701(8) 0.72729(13) 0.0799(5) Uani 1 d . . C2A C 0.8926(2) 0.23421(9) 0.4230(2) 0.0594(5) Uani 1 d . . H2A1 H 0.9619 0.20690 0.3814 0.071 Uiso 1 calc R . O3A O 0.73313(15) 0.32020(7) 0.74778(12) 0.0760(4) Uani 1 d . . C3A C 0.7700(2) 0.25656(9) 0.3405(2) 0.0647(5) Uani 1 d . . H3A H 0.6748 0.25520 0.3782 0.078 Uiso 1 calc R . C4A C 0.8506(2) 0.20302(9) 0.5383(2) 0.0608(5) Uani 1 d . . H4A H 0.9402 0.19237 0.5801 0.073 Uiso 1 calc R . C5A C 0.7647(2) 0.14176(10) 0.5228(2) 0.0767(7) Uani 1 d . . H5A1 H 0.7411 0.12416 0.5973 0.115 Uiso 1 calc R . H5A2 H 0.8214 0.11112 0.4801 0.115 Uiso 1 calc R . H5A3 H 0.6768 0.15099 0.4812 0.115 Uiso 1 calc R . C6A C 0.8299(2) 0.28048(10) 0.6969(2) 0.0636(5) Uani 1 d . . C7A C 0.7893(3) 0.36150(13) 0.8386(2) 0.0978(8) Uani 1 d . . H7A1 H 0.8743 0.38455 0.8115 0.117 Uiso 1 calc R . H7A2 H 0.8167 0.33594 0.9054 0.117 Uiso 1 calc R . C8A C 0.6727(3) 0.40773(12) 0.8700(2) 0.0850(7) Uani 1 d . . C9A C 0.6001(3) 0.4024(2) 0.9721(2) 0.1188(10) Uani 1 d . . H9A H 0.6252 0.3703 1.0247 0.143 Uiso 1 calc R . C10A C 0.4867(4) 0.4456(2) 0.9975(3) 0.1495(11) Uani 1 d U . H10A H 0.4338 0.4408 1.0654 0.179 Uiso 1 calc R . C11A C 0.4553(4) 0.4931(2) 0.9250(4) 0.1730(14) Uani 1 d . . H11A H 0.3830 0.5227 0.9437 0.208 Uiso 1 calc R . C12A C 0.5271(4) 0.4988(2) 0.8249(5) 0.152(2) Uani 1 d . . H12A H 0.5017 0.5314 0.7733 0.182 Uiso 1 calc R . C13A C 0.6381(4) 0.45712(14) 0.7970(3) 0.1115(11) Uani 1 d . . H13A H 0.6895 0.46265 0.7285 0.134 Uiso 1 calc R . C14A C 0.8012(3) 0.38198(11) 0.2939(2) 0.0832(7) Uani 1 d . . H14A H 0.7850 0.37440 0.2120 0.100 Uiso 1 calc R . H14B H 0.8851 0.40999 0.3007 0.100 Uiso 1 calc R . C15A C 0.6716(3) 0.41740(9) 0.3408(2) 0.0725(6) Uani 1 d . . C16A C 0.6062(4) 0.39827(14) 0.4389(3) 0.1316(11) Uani 1 d . . H16A H 0.6360 0.36072 0.4760 0.158 Uiso 1 calc R . C17A C 0.4936(5) 0.4351(2) 0.4846(3) 0.1589(12) Uani 1 d . . H17A H 0.4583 0.4262 0.5583 0.191 Uiso 1 calc R . C18A C 0.4331(4) 0.48580(14) 0.4191(3) 0.1381(12) Uani 1 d . . H18A H 0.3439 0.50362 0.4388 0.166 Uiso 1 calc R . C19A C 0.5065(4) 0.50734(13) 0.3289(3) 0.1066(10) Uani 1 d . . H19A H 0.4796 0.54582 0.2935 0.128 Uiso 1 calc R . C20A C 0.6239(3) 0.47237(11) 0.2869(2) 0.0872(8) Uani 1 d . . H20A H 0.6713 0.48661 0.2206 0.105 Uiso 1 calc R . C21A C 0.76528(4) 0.22809(3) 0.22308(5) 0.0743(6) Uani 1 d D . S1A S 0.65119(6) 0.16787(3) 0.18247(5) 0.1093(3) Uani 0.6870(13) d PDU 1 C22A C 0.84633(9) 0.24493(3) 0.12745(5) 0.0962(11) Uani 0.6870(13) d PDU 1 H22A H 0.89869 0.28326 0.12612 0.115 Uiso 0.6870(13) calc PR 1 C23A C 0.84801(8) 0.20363(3) 0.03378(5) 0.120(2) Uani 0.6870(13) d PDU 1 H23A H 0.91455 0.20273 -0.02664 0.144 Uiso 0.6870(13) calc PR 1 C24A C 0.72938(8) 0.16395(4) 0.04937(5) 0.0996(12) Uani 0.6870(13) d PDU 1 H24A H 0.69465 0.13699 -0.00874 0.120 Uiso 0.6870(13) calc PR 1 S1C S 0.89743(6) 0.23819(4) 0.12244(6) 0.1029(8) Uani 0.3130(13) d PDU 2 C22C C 0.65015(7) 0.19761(4) 0.16933(5) 0.066(2) Uani 0.3130(13) d PDU 2 H22C H 0.55856 0.19719 0.20306 0.079 Uiso 0.3130(13) calc PR 2 C23C C 0.67438(7) 0.16778(5) 0.06429(5) 0.101(2) Uani 0.3130(13) d PDU 2 H23C H 0.61761 0.13638 0.02878 0.121 Uiso 0.3130(13) calc PR 2 C24C C 0.80136(7) 0.19479(5) 0.02357(5) 0.084(2) Uani 0.3130(13) d PDU 2 H24C H 0.83219 0.18964 -0.05248 0.101 Uiso 0.3130(13) calc PR 2 N1B N 0.3410(2) 0.18771(8) -0.0980(2) 0.0715(5) Uani 1 d . . C1B C 0.4463(2) 0.20491(10) -0.1737(2) 0.0654(5) Uani 1 d . . O1B O 0.5413(2) 0.17397(8) -0.21790(14) 0.0825(5) Uani 1 d . . N2B N 0.26916(15) 0.25662(7) -0.36354(13) 0.0599(4) Uani 1 d . . H2B H 0.17885 0.25025 -0.34862 0.072 Uiso 1 calc R . O2B O 0.45680(14) 0.22830(8) -0.48140(13) 0.0759(4) Uani 1 d . . C2B C 0.3912(2) 0.27453(9) -0.1768(2) 0.0588(5) Uani 1 d . . H2B1 H 0.4572 0.30330 -0.1348 0.071 Uiso 1 calc R . O3B O 0.23507(14) 0.18261(7) -0.49929(12) 0.0736(4) Uani 1 d . . C3B C 0.2678(2) 0.25048(10) -0.0970(2) 0.0648(5) Uani 1 d . . H3B H 0.1742 0.24897 -0.1375 0.078 Uiso 1 calc R . C4B C 0.3505(2) 0.30297(9) -0.2952(2) 0.0576(5) Uani 1 d . . H4B H 0.4403 0.31335 -0.3366 0.069 Uiso 1 calc R . C5B C 0.2633(2) 0.36483(9) -0.2804(2) 0.0710(6) Uani 1 d . . H5B1 H 0.2388 0.38194 -0.3552 0.107 Uiso 1 calc R . H5B2 H 0.3202 0.39583 -0.2385 0.107 Uiso 1 calc R . H5B3 H 0.1759 0.35571 -0.2383 0.107 Uiso 1 calc R . C6B C 0.3322(2) 0.22364(10) -0.4493(2) 0.0632(5) Uani 1 d . . C7B C 0.2961(3) 0.13994(13) -0.5840(2) 0.0969(8) Uani 1 d . . H7B1 H 0.3785 0.11703 -0.5515 0.116 Uiso 1 calc R . H7B2 H 0.3287 0.16415 -0.6508 0.116 Uiso 1 calc R . C8B C 0.1793(2) 0.09331(11) -0.6184(2) 0.0718(6) Uani 1 d . . C9B C 0.1484(3) 0.03827(14) -0.5526(3) 0.1021(9) Uani 1 d . . H9B H 0.2020 0.02892 -0.4864 0.122 Uiso 1 calc R . C10B C 0.0329(4) -0.00339(13) -0.5889(3) 0.1171(11) Uani 1 d . . H10B H 0.0109 -0.04066 -0.5477 0.141 Uiso 1 calc R . C11B C -0.0424(4) 0.01283(15) -0.6835(3) 0.1108(10) Uani 1 d . . H11B H -0.1185 -0.01381 -0.7061 0.133 Uiso 1 calc R . C12B C -0.0150(3) 0.0645(2) -0.7470(3) 0.1066(10) Uani 1 d . . H12B H -0.0712 0.0740 -0.8118 0.128 Uiso 1 calc R . C13B C 0.0967(3) 0.10350(11) -0.7155(2) 0.0771(7) Uani 1 d . . H13B H 0.1182 0.13881 -0.7620 0.093 Uiso 1 calc R . C14B C 0.3086(3) 0.12463(11) -0.0492(2) 0.0862(8) Uani 1 d . . H14C H 0.2991 0.12912 0.0340 0.103 Uiso 1 calc R . H14D H 0.3905 0.09635 -0.0636 0.103 Uiso 1 calc R . C15B C 0.1729(3) 0.09275(10) -0.0956(2) 0.0724(6) Uani 1 d . . C16B C 0.1206(3) 0.10644(13) -0.2029(3) 0.1026(9) Uani 1 d . . H16B H 0.1669 0.13740 -0.2478 0.123 Uiso 1 calc R . C17B C -0.0015(4) 0.0749(2) -0.2468(3) 0.1356(12) Uani 1 d . . H17B H -0.0351 0.0836 -0.3212 0.163 Uiso 1 calc R . C18B C -0.0720(4) 0.0299(2) -0.1767(4) 0.1339(13) Uani 1 d . . H18B H -0.1580 0.0108 -0.2014 0.161 Uiso 1 calc R . C19B C -0.0126(4) 0.0137(2) -0.0692(3) 0.1209(11) Uani 1 d . . H19B H -0.0546 -0.0185 -0.0242 0.145 Uiso 1 calc R . C20B C 0.1084(3) 0.04564(12) -0.0309(2) 0.0964(9) Uani 1 d . . H20B H 0.1477 0.03504 0.0408 0.116 Uiso 1 calc R . C21B C 0.25464(5) 0.28096(2) 0.02016(5) 0.0737(6) Uani 1 d D . S1B S 0.15229(7) 0.34807(3) 0.04088(4) 0.0959(3) Uani 0.6781(14) d PDU 3 C22B C 0.31030(11) 0.26210(3) 0.12478(4) 0.0973(12) Uani 0.6781(14) d PDU 3 H22B H 0.36193 0.22375 0.13148 0.117 Uiso 0.6781(14) calc PR 3 C23B C 0.28870(10) 0.30064(3) 0.21935(5) 0.132(2) Uani 0.6781(14) d PDU 3 H23B H 0.32519 0.29433 0.29361 0.159 Uiso 0.6781(14) calc PR 3 C24B C 0.20253(10) 0.35035(3) 0.18252(5) 0.1105(12) Uani 0.6781(14) d PDU 3 H24B H 0.17330 0.38330 0.23185 0.133 Uiso 0.6781(14) calc PR 3 S1D S 0.37380(7) 0.26809(4) 0.13014(6) 0.1207(9) Uani 0.3219(14) d PDU 4 C22D C 0.15355(8) 0.32497(4) 0.05597(5) 0.119(3) Uani 0.3219(14) d PDU 4 H22D H 0.07465 0.33527 0.00913 0.142 Uiso 0.3219(14) calc PR 4 C23D C 0.17056(8) 0.35358(4) 0.16191(5) 0.117(3) Uani 0.3219(14) d PDU 4 H23D H 0.11518 0.38690 0.19267 0.141 Uiso 0.3219(14) calc PR 4 C24D C 0.28569(8) 0.32314(4) 0.21337(5) 0.097(2) Uani 0.3219(14) d PDU 4 H24D H 0.31392 0.33201 0.28905 0.117 Uiso 0.3219(14) calc PR 4 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 N1A 0.0766(10) 0.0555(8) 0.0818(10) -0.0018(8) -0.0034(8) 0.0082(8) O1A 0.0823(9) 0.0905(10) 0.0852(9) -0.0015(8) -0.0075(7) -0.0227(8) C1A 0.0586(10) 0.0656(10) 0.0718(10) -0.0031(9) 0.0039(9) 0.0005(9) N2A 0.0436(7) 0.0724(9) 0.0732(8) -0.0130(7) -0.0005(6) 0.0001(7) O2A 0.0534(7) 0.0990(10) 0.0871(8) -0.0044(8) -0.0078(6) -0.0008(8) C2A 0.0523(9) 0.0611(9) 0.0648(9) -0.0081(8) 0.0032(8) 0.0078(8) O3A 0.0623(7) 0.0840(8) 0.0818(8) -0.0226(7) -0.0029(6) -0.0084(7) C3A 0.0564(9) 0.0589(9) 0.0787(11) -0.0013(9) -0.0026(9) 0.0049(9) C4A 0.0502(8) 0.0602(9) 0.0720(10) -0.0032(8) 0.0028(8) 0.0076(8) C5A 0.0748(12) 0.0543(10) 0.1009(14) 0.0012(10) 0.0001(11) -0.0069(10) C6A 0.0521(9) 0.0700(10) 0.0688(9) -0.0050(9) 0.0045(8) -0.0042(9) C7A 0.097(2) 0.0992(15) 0.0976(13) -0.0416(12) -0.0181(12) -0.0080(14) C8A 0.0799(13) 0.0923(13) 0.0828(12) -0.0295(11) 0.0087(11) -0.0220(12) C9A 0.115(2) 0.152(2) 0.0894(14) -0.0516(14) 0.0094(14) -0.037(2) C10A 0.122(2) 0.199(2) 0.128(2) -0.090(2) 0.041(2) -0.067(2) C11A 0.126(2) 0.147(2) 0.247(3) -0.124(2) 0.034(2) -0.037(2) C12A 0.130(3) 0.087(2) 0.239(4) -0.041(2) 0.000(3) 0.004(2) C13A 0.111(2) 0.090(2) 0.133(2) -0.003(2) 0.020(2) -0.009(2) C14A 0.099(2) 0.0680(11) 0.0822(12) 0.0134(10) 0.0047(12) 0.0061(12) C15A 0.0960(14) 0.0520(9) 0.0696(10) 0.0057(8) 0.0044(10) 0.0044(10) C16A 0.180(3) 0.0864(14) 0.129(2) 0.0416(14) 0.070(2) 0.044(2) C17A 0.201(3) 0.106(2) 0.170(2) 0.055(2) 0.103(2) 0.063(2) C18A 0.153(2) 0.0880(15) 0.174(3) 0.039(2) 0.060(2) 0.055(2) C19A 0.130(2) 0.0698(12) 0.120(2) 0.0139(14) -0.002(2) 0.0277(14) C20A 0.111(2) 0.0645(11) 0.0856(13) 0.0219(10) -0.0030(13) 0.0034(13) C21A 0.0797(12) 0.0712(11) 0.0720(11) -0.0046(10) -0.0121(10) 0.0017(11) S1A 0.0892(5) 0.1045(6) 0.1340(7) -0.0345(5) -0.0206(5) -0.0121(5) C22A 0.121(2) 0.086(2) 0.082(2) -0.024(2) 0.033(2) -0.003(2) C23A 0.158(3) 0.113(3) 0.089(2) -0.017(2) -0.008(2) 0.007(3) C24A 0.103(2) 0.101(2) 0.095(2) -0.030(2) -0.031(2) 0.020(2) S1C 0.1016(14) 0.1080(15) 0.0990(12) -0.0050(12) 0.0152(11) -0.0033(13) C22C 0.035(2) 0.054(2) 0.109(4) -0.024(2) -0.004(2) -0.022(2) C23C 0.094(4) 0.111(4) 0.098(4) -0.005(3) -0.039(3) 0.014(4) C24C 0.108(4) 0.083(3) 0.061(3) 0.001(3) -0.003(3) -0.014(3) N1B 0.0758(10) 0.0568(8) 0.0819(10) 0.0040(8) -0.0007(8) 0.0032(8) C1B 0.0558(9) 0.0660(10) 0.0743(10) -0.0063(9) -0.0015(8) 0.0046(9) O1B 0.0723(8) 0.0855(9) 0.0898(9) -0.0091(8) 0.0015(7) 0.0219(8) N2B 0.0453(7) 0.0636(8) 0.0710(8) -0.0113(7) -0.0018(6) -0.0034(7) O2B 0.0517(6) 0.0899(9) 0.0861(8) -0.0140(8) 0.0067(6) -0.0029(7) C2B 0.0520(8) 0.0582(9) 0.0660(9) -0.0062(8) -0.0032(7) 0.0000(8) O3B 0.0538(6) 0.0841(8) 0.0829(8) -0.0266(7) 0.0026(6) -0.0016(7) C3B 0.0604(10) 0.0606(10) 0.0734(10) -0.0007(9) 0.0068(9) 0.0045(9) C4B 0.0483(8) 0.0540(8) 0.0704(9) -0.0066(8) 0.0007(8) -0.0050(8) C5B 0.0678(11) 0.0539(10) 0.0913(13) -0.0020(9) -0.0034(10) 0.0044(9) C6B 0.0578(9) 0.0654(10) 0.0664(9) -0.0065(8) -0.0042(8) -0.0021(9) C7B 0.0845(14) 0.1021(15) 0.1042(14) -0.0458(12) 0.0117(12) -0.0102(13) C8B 0.0666(11) 0.0727(11) 0.0761(11) -0.0186(10) -0.0017(9) 0.0099(10) C9B 0.121(2) 0.089(2) 0.096(2) 0.0082(13) 0.0026(15) 0.0276(15) C10B 0.146(2) 0.0649(13) 0.141(2) 0.0074(15) 0.043(2) -0.010(2) C11B 0.108(2) 0.091(2) 0.133(2) -0.033(2) -0.004(2) -0.006(2) C12B 0.094(2) 0.121(2) 0.105(2) -0.0397(14) -0.0081(14) 0.004(2) C13B 0.0801(13) 0.0758(12) 0.0754(11) -0.0067(10) 0.0032(10) 0.0067(11) C14B 0.103(2) 0.0637(11) 0.0921(13) 0.0194(10) -0.0087(13) -0.0048(12) C15B 0.0853(13) 0.0524(9) 0.0795(11) 0.0026(9) 0.0020(10) 0.0041(10) C16B 0.119(2) 0.0780(14) 0.111(2) 0.0241(13) -0.0251(15) -0.0141(15) C17B 0.143(2) 0.097(2) 0.167(2) 0.025(2) -0.073(2) -0.032(2) C18B 0.118(2) 0.095(2) 0.188(3) 0.000(2) -0.038(2) -0.029(2) C19B 0.141(2) 0.101(2) 0.121(2) 0.008(2) 0.018(2) -0.034(2) C20B 0.124(2) 0.0742(13) 0.091(2) 0.0093(12) 0.0053(15) -0.0050(14) C21B 0.0820(13) 0.0667(11) 0.0723(10) -0.0031(10) 0.0155(10) 0.0076(11) S1B 0.0951(6) 0.0771(5) 0.1155(6) -0.0146(5) 0.0220(5) 0.0101(5) C22B 0.109(2) 0.107(2) 0.076(2) -0.008(2) -0.013(2) 0.020(2) C23B 0.176(4) 0.123(3) 0.097(2) -0.010(2) 0.009(3) 0.003(3) C24B 0.122(2) 0.110(2) 0.100(2) -0.045(2) 0.051(2) -0.007(2) S1D 0.138(2) 0.118(2) 0.1060(13) -0.0169(13) -0.0245(13) 0.0343(14) C22D 0.102(5) 0.117(5) 0.137(5) -0.012(4) 0.000(4) 0.007(4) C23D 0.115(4) 0.116(4) 0.121(4) -0.005(4) 0.020(4) 0.015(4) C24D 0.120(4) 0.096(4) 0.076(3) -0.014(3) 0.004(3) 0.017(4) _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 N1A C1A 1.354(3) . ? N1A C14A 1.425(3) . ? N1A C3A 1.486(3) . ? O1A C1A 1.218(3) . ? C1A C2A 1.523(3) . ? N2A C6A 1.331(2) . ? N2A C4A 1.474(2) . ? N2A H2A 0.86 . ? O2A C6A 1.213(2) . ? C2A C4A 1.532(3) . ? C2A C3A 1.546(3) . ? C2A H2A1 0.98 . ? O3A C6A 1.349(2) . ? O3A C7A 1.449(3) . ? C3A C21A 1.480(2) . ? C3A H3A 0.98 . ? C4A C5A 1.507(3) . ? C4A H4A 0.98 . ? C5A H5A1 0.96 . ? C5A H5A2 0.96 . ? C5A H5A3 0.96 . ? C7A C8A 1.485(4) . ? C7A H7A1 0.97 . ? C7A H7A2 0.97 . ? C8A C9A 1.361(4) . ? C8A C13A 1.364(4) . ? C9A C10A 1.408(5) . ? C9A H9A 0.93 . ? C10A C11A 1.325(6) . ? C10A H10A 0.93 . ? C11A C12A 1.339(7) . ? C11A H11A 0.93 . ? C12A C13A 1.378(5) . ? C12A H12A 0.93 . ? C13A H13A 0.93 . ? C14A C15A 1.504(3) . ? C14A H14A 0.97 . ? C14A H14B 0.97 . ? C15A C16A 1.344(4) . ? C15A C20A 1.371(3) . ? C16A C17A 1.393(5) . ? C16A H16A 0.93 . ? C17A C18A 1.410(5) . ? C17A H17A 0.93 . ? C18A C19A 1.321(5) . ? C18A H18A 0.93 . ? C19A C20A 1.391(4) . ? C19A H19A 0.93 . ? C20A H20A 0.93 . ? C21A C22A 1.3796(8) . ? C21A C22C 1.3809(8) . ? C21A S1A 1.6978(7) . ? C21A S1C 1.6979(7) . ? S1A C24A 1.7012(7) . ? C22A C23A 1.3803(8) . ? C22A H22A 0.93 . ? C23A C24A 1.3800(9) . ? C23A H23A 0.93 . ? C24A H24A 0.93 . ? S1C C24C 1.7011(9) . ? C22C C23C 1.3807(9) . ? C22C H22C 0.93 . ? C23C C24C 1.3804(9) . ? C23C H23C 0.93 . ? C24C H24C 0.93 . ? N1B C1B 1.355(3) . ? N1B C14B 1.456(3) . ? N1B C3B 1.466(3) . ? C1B O1B 1.200(2) . ? C1B C2B 1.531(3) . ? N2B C6B 1.338(2) . ? N2B C4B 1.451(2) . ? N2B H2B 0.86 . ? O2B C6B 1.211(2) . ? C2B C4B 1.535(3) . ? C2B C3B 1.548(3) . ? C2B H2B1 0.98 . ? O3B C6B 1.362(2) . ? O3B C7B 1.434(3) . ? C3B C21B 1.499(2) . ? C3B H3B 0.98 . ? C4B C5B 1.524(3) . ? C4B H4B 0.98 . ? C5B H5B1 0.96 . ? C5B H5B2 0.96 . ? C5B H5B3 0.96 . ? C7B C8B 1.499(3) . ? C7B H7B1 0.97 . ? C7B H7B2 0.97 . ? C8B C13B 1.371(3) . ? C8B C9B 1.401(4) . ? C9B C10B 1.433(4) . ? C9B H9B 0.93 . ? C10B C11B 1.336(5) . ? C10B H10B 0.93 . ? C11B C12B 1.324(4) . ? C11B H11B 0.93 . ? C12B C13B 1.357(4) . ? C12B H12B 0.93 . ? C13B H13B 0.93 . ? C14B C15B 1.511(3) . ? C14B H14C 0.97 . ? C14B H14D 0.97 . ? C15B C16B 1.359(4) . ? C15B C20B 1.366(3) . ? C16B C17B 1.396(5) . ? C16B H16B 0.93 . ? C17B C18B 1.398(5) . ? C17B H17B 0.93 . ? C18B C19B 1.397(5) . ? C18B H18B 0.93 . ? C19B C20B 1.369(5) . ? C19B H19B 0.93 . ? C20B H20B 0.93 . ? C21B C22D 1.3686(8) . ? C21B C22B 1.3690(7) . ? C21B S1D 1.6983(7) . ? C21B S1B 1.6984(7) . ? S1B C24B 1.7002(7) . ? C22B C23B 1.3686(8) . ? C22B H22B 0.93 . ? C23B C24B 1.3685(9) . ? C23B H23B 0.93 . ? C24B H24B 0.93 . ? S1D C24D 1.7001(9) . ? C22D C23D 1.3689(8) . ? C22D H22D 0.93 . ? C23D C24D 1.3689(9) . ? C23D H23D 0.93 . ? C24D H24D 0.93 . ? 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 C1A N1A C14A 132.2(2) . . ? C1A N1A C3A 94.62(15) . . ? C14A N1A C3A 133.2(2) . . ? O1A C1A N1A 129.7(2) . . ? O1A C1A C2A 137.6(2) . . ? N1A C1A C2A 92.69(15) . . ? C6A N2A C4A 121.16(15) . . ? C6A N2A H2A 119.42 . . ? C4A N2A H2A 119.42 . . ? C1A C2A C4A 119.4(2) . . ? C1A C2A C3A 85.80(14) . . ? C4A C2A C3A 118.5(2) . . ? C1A C2A H2A1 110.34 . . ? C4A C2A H2A1 110.34 . . ? C3A C2A H2A1 110.34 . . ? C6A O3A C7A 116.2(2) . . ? C21A C3A N1A 114.82(15) . . ? C21A C3A C2A 117.71(14) . . ? N1A C3A C2A 86.86(14) . . ? C21A C3A H3A 111.75 . . ? N1A C3A H3A 111.75 . . ? C2A C3A H3A 111.75 . . ? N2A C4A C5A 110.1(2) . . ? N2A C4A C2A 109.80(15) . . ? C5A C4A C2A 112.7(2) . . ? N2A C4A H4A 108.04 . . ? C5A C4A H4A 108.04 . . ? C2A C4A H4A 108.04 . . ? C4A C5A H5A1 109.47 . . ? C4A C5A H5A2 109.47 . . ? H5A1 C5A H5A2 109.5 . . ? C4A C5A H5A3 109.47 . . ? H5A1 C5A H5A3 109.5 . . ? H5A2 C5A H5A3 109.5 . . ? O2A C6A N2A 126.9(2) . . ? O2A C6A O3A 122.8(2) . . ? N2A C6A O3A 110.2(2) . . ? O3A C7A C8A 107.6(2) . . ? O3A C7A H7A1 110.20 . . ? C8A C7A H7A1 110.20 . . ? O3A C7A H7A2 110.20 . . ? C8A C7A H7A2 110.20 . . ? H7A1 C7A H7A2 108.5 . . ? C9A C8A C13A 118.8(3) . . ? C9A C8A C7A 121.1(3) . . ? C13A C8A C7A 120.1(2) . . ? C8A C9A C10A 119.6(3) . . ? C8A C9A H9A 120.2 . . ? C10A C9A H9A 120.2 . . ? C11A C10A C9A 120.2(3) . . ? C11A C10A H10A 119.9 . . ? C9A C10A H10A 119.9 . . ? C10A C11A C12A 120.2(4) . . ? C10A C11A H11A 119.9 . . ? C12A C11A H11A 119.9 . . ? C11A C12A C13A 121.0(4) . . ? C11A C12A H12A 119.5 . . ? C13A C12A H12A 119.5 . . ? C8A C13A C12A 120.0(3) . . ? C8A C13A H13A 120.0 . . ? C12A C13A H13A 120.0 . . ? N1A C14A C15A 116.8(2) . . ? N1A C14A H14A 108.10 . . ? C15A C14A H14A 108.10 . . ? N1A C14A H14B 108.10 . . ? C15A C14A H14B 108.10 . . ? H14A C14A H14B 107.3 . . ? C16A C15A C20A 119.0(2) . . ? C16A C15A C14A 121.1(2) . . ? C20A C15A C14A 119.7(2) . . ? C15A C16A C17A 119.5(3) . . ? C15A C16A H16A 120.2 . . ? C17A C16A H16A 120.2 . . ? C16A C17A C18A 120.0(3) . . ? C16A C17A H17A 120.0 . . ? C18A C17A H17A 120.0 . . ? C19A C18A C17A 118.3(3) . . ? C19A C18A H18A 120.9 . . ? C17A C18A H18A 120.9 . . ? C18A C19A C20A 119.9(3) . . ? C18A C19A H19A 120.1 . . ? C20A C19A H19A 120.1 . . ? C15A C20A C19A 121.6(2) . . ? C15A C20A H20A 119.20 . . ? C19A C20A H20A 119.2 . . ? C22A C21A C3A 128.17(9) . . ? C22C C21A C3A 128.02(8) . . ? C22A C21A S1A 107.49(5) . . ? C3A C21A S1A 124.32(8) . . ? C22C C21A S1C 107.42(5) . . ? C3A C21A S1C 123.96(8) . . ? C21A S1A C24A 91.26(4) . . ? C21A C22A C23A 118.53(6) . . ? C21A C22A H22A 120.74 . . ? C23A C22A H22A 120.74 . . ? C24A C23A C22A 104.94(6) . . ? C24A C23A H23A 127.53 . . ? C22A C23A H23A 127.53 . . ? C23A C24A S1A 115.23(5) . . ? C23A C24A H24A 122.39 . . ? S1A C24A H24A 122.39 . . ? C21A S1C C24C 91.26(4) . . ? C23C C22C C21A 118.37(6) . . ? C23C C22C H22C 120.82 . . ? C21A C22C H22C 120.82 . . ? C24C C23C C22C 104.84(6) . . ? C24C C23C H23C 127.58 . . ? C22C C23C H23C 127.58 . . ? C23C C24C S1C 115.20(5) . . ? C23C C24C H24C 122.40 . . ? S1C C24C H24C 122.40 . . ? C1B N1B C14B 129.4(2) . . ? C1B N1B C3B 95.8(2) . . ? C14B N1B C3B 134.4(2) . . ? O1B C1B N1B 131.1(2) . . ? O1B C1B C2B 137.4(2) . . ? N1B C1B C2B 91.48(15) . . ? C6B N2B C4B 121.17(15) . . ? C6B N2B H2B 119.41 . . ? C4B N2B H2B 119.41 . . ? C1B C2B C4B 117.6(2) . . ? C1B C2B C3B 85.74(14) . . ? C4B C2B C3B 118.5(2) . . ? C1B C2B H2B1 110.93 . . ? C4B C2B H2B1 110.93 . . ? C3B C2B H2B1 110.93 . . ? C6B O3B C7B 114.6(2) . . ? N1B C3B C21B 114.80(15) . . ? N1B C3B C2B 86.73(14) . . ? C21B C3B C2B 117.55(14) . . ? N1B C3B H3B 111.84 . . ? C21B C3B H3B 111.84 . . ? C2B C3B H3B 111.84 . . ? N2B C4B C5B 110.31(15) . . ? N2B C4B C2B 110.79(15) . . ? C5B C4B C2B 110.6(2) . . ? N2B C4B H4B 108.36 . . ? C5B C4B H4B 108.36 . . ? C2B C4B H4B 108.36 . . ? C4B C5B H5B1 109.47 . . ? C4B C5B H5B2 109.47 . . ? H5B1 C5B H5B2 109.5 . . ? C4B C5B H5B3 109.47 . . ? H5B1 C5B H5B3 109.5 . . ? H5B2 C5B H5B3 109.5 . . ? O2B C6B N2B 126.8(2) . . ? O2B C6B O3B 122.9(2) . . ? N2B C6B O3B 110.4(2) . . ? O3B C7B C8B 107.3(2) . . ? O3B C7B H7B1 110.26 . . ? C8B C7B H7B1 110.26 . . ? O3B C7B H7B2 110.26 . . ? C8B C7B H7B2 110.26 . . ? H7B1 C7B H7B2 108.5 . . ? C13B C8B C9B 117.1(2) . . ? C13B C8B C7B 120.9(2) . . ? C9B C8B C7B 121.9(2) . . ? C8B C9B C10B 119.0(3) . . ? C8B C9B H9B 120.5 . . ? C10B C9B H9B 120.5 . . ? C11B C10B C9B 118.1(3) . . ? C11B C10B H10B 121.0 . . ? C9B C10B H10B 121.0 . . ? C12B C11B C10B 123.9(3) . . ? C12B C11B H11B 118.0 . . ? C10B C11B H11B 118.0 . . ? C11B C12B C13B 118.6(3) . . ? C11B C12B H12B 120.7 . . ? C13B C12B H12B 120.7 . . ? C12B C13B C8B 123.2(2) . . ? C12B C13B H13B 118.4 . . ? C8B C13B H13B 118.42 . . ? N1B C14B C15B 115.2(2) . . ? N1B C14B H14C 108.47 . . ? C15B C14B H14C 108.47 . . ? N1B C14B H14D 108.47 . . ? C15B C14B H14D 108.47 . . ? H14C C14B H14D 107.5 . . ? C16B C15B C20B 119.6(2) . . ? C16B C15B C14B 121.6(2) . . ? C20B C15B C14B 118.6(2) . . ? C15B C16B C17B 121.2(3) . . ? C15B C16B H16B 119.4 . . ? C17B C16B H16B 119.4 . . ? C16B C17B C18B 118.5(3) . . ? C16B C17B H17B 120.7 . . ? C18B C17B H17B 120.7 . . ? C19B C18B C17B 119.6(3) . . ? C19B C18B H18B 120.2 . . ? C17B C18B H18B 120.2 . . ? C20B C19B C18B 119.2(3) . . ? C20B C19B H19B 120.4 . . ? C18B C19B H19B 120.4 . . ? C15B C20B C19B 121.6(3) . . ? C15B C20B H20B 119.2 . . ? C19B C20B H20B 119.2 . . ? C22D C21B C3B 127.62(9) . . ? C22B C21B C3B 130.24(9) . . ? C22D C21B S1D 108.53(5) . . ? C3B C21B S1D 123.78(8) . . ? C22B C21B S1B 108.47(5) . . ? C3B C21B S1B 121.25(8) . . ? C21B S1B C24B 90.48(4) . . ? C23B C22B C21B 118.89(6) . . ? C23B C22B H22B 120.56 . . ? C21B C22B H22B 120.56 . . ? C24B C23B C22B 106.08(5) . . ? C24B C23B H23B 126.96 . . ? C22B C23B H23B 126.96 . . ? C23B C24B S1B 115.77(5) . . ? C23B C24B H24B 122.11 . . ? S1B C24B H24B 122.11 . . ? C21B S1D C24D 90.52(4) . . ? C21B C22D C23D 118.86(6) . . ? C21B C22D H22D 120.57 . . ? C23D C22D H22D 120.57 . . ? C22D C23D C24D 105.99(6) . . ? C22D C23D H23D 127.01 . . ? C24D C23D H23D 127.01 . . ? C23D C24D S1D 115.75(5) . . ? C23D C24D H24D 122.13 . . ? S1D C24D H24D 122.13 . . ? 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 C14A N1A C1A O1A 2.9(4) . . . . ? C3A N1A C1A O1A -177.3(2) . . . . ? C14A N1A C1A C2A -178.4(2) . . . . ? C3A N1A C1A C2A 1.4(2) . . . . ? O1A C1A C2A C4A 56.6(3) . . . . ? N1A C1A C2A C4A -121.9(2) . . . . ? O1A C1A C2A C3A 177.2(3) . . . . ? N1A C1A C2A C3A -1.37(15) . . . . ? C1A N1A C3A C21A -120.6(2) . . . . ? C14A N1A C3A C21A 59.2(3) . . . . ? C1A N1A C3A C2A -1.4(2) . . . . ? C14A N1A C3A C2A 178.4(2) . . . . ? C1A C2A C3A C21A 117.7(2) . . . . ? C4A C2A C3A C21A -120.9(2) . . . . ? C1A C2A C3A N1A 1.25(13) . . . . ? C4A C2A C3A N1A 122.6(2) . . . . ? C6A N2A C4A C5A 132.9(2) . . . . ? C6A N2A C4A C2A -102.5(2) . . . . ? C1A C2A C4A N2A 40.5(2) . . . . ? C3A C2A C4A N2A -61.6(2) . . . . ? C1A C2A C4A C5A 163.6(2) . . . . ? C3A C2A C4A C5A 61.5(2) . . . . ? C4A N2A C6A O2A 2.2(3) . . . . ? C4A N2A C6A O3A 179.7(2) . . . . ? C7A O3A C6A O2A 2.8(3) . . . . ? C7A O3A C6A N2A -174.7(2) . . . . ? C6A O3A C7A C8A 171.5(2) . . . . ? O3A C7A C8A C9A 107.6(3) . . . . ? O3A C7A C8A C13A -73.3(3) . . . . ? C13A C8A C9A C10A 3.1(4) . . . . ? C7A C8A C9A C10A -177.8(3) . . . . ? C8A C9A C10A C11A -3.1(5) . . . . ? C9A C10A C11A C12A 2.7(6) . . . . ? C10A C11A C12A C13A -2.4(6) . . . . ? C9A C8A C13A C12A -2.8(5) . . . . ? C7A C8A C13A C12A 178.1(3) . . . . ? C11A C12A C13A C8A 2.4(6) . . . . ? C1A N1A C14A C15A -105.4(3) . . . . ? C3A N1A C14A C15A 74.8(3) . . . . ? N1A C14A C15A C16A 10.0(4) . . . . ? N1A C14A C15A C20A -173.8(2) . . . . ? C20A C15A C16A C17A -1.1(5) . . . . ? C14A C15A C16A C17A 175.1(3) . . . . ? C15A C16A C17A C18A 10.3(5) . . . . ? C16A C17A C18A C19A -16.2(6) . . . . ? C17A C18A C19A C20A 12.8(5) . . . . ? C16A C15A C20A C19A -2.4(4) . . . . ? C14A C15A C20A C19A -178.6(2) . . . . ? C18A C19A C20A C15A -3.7(5) . . . . ? N1A C3A C21A C22A 19.5(2) . . . . ? C2A C3A C21A C22A -80.6(2) . . . . ? N1A C3A C21A C22C -133.72(13) . . . . ? C2A C3A C21A C22C 126.21(14) . . . . ? N1A C3A C21A S1A -159.06(11) . . . . ? C2A C3A C21A S1A 100.87(15) . . . . ? N1A C3A C21A S1C 36.3(2) . . . . ? C2A C3A C21A S1C -63.8(2) . . . . ? C22A C21A S1A C24A 5.51(6) . . . . ? C22C C21A S1A C24A 76.65(9) . . . . ? C3A C21A S1A C24A -175.70(10) . . . . ? S1C C21A S1A C24A -9.22(6) . . . . ? C22C C21A C22A C23A -34.99(9) . . . . ? C3A C21A C22A C23A 166.15(11) . . . . ? S1A C21A C22A C23A -15.12(8) . . . . ? S1C C21A C22A C23A 88.3(2) . . . . ? C21A C22A C23A C24A 17.75(9) . . . . ? C22A C23A C24A S1A -12.45(8) . . . . ? C21A S1A C24A C23A 4.32(7) . . . . ? C22A C21A S1C C24C -65.70(15) . . . . ? C22C C21A S1C C24C -6.02(7) . . . . ? C3A C21A S1C C24C -177.78(10) . . . . ? S1A C21A S1C C24C 15.68(6) . . . . ? C22A C21A C22C C23C 28.64(10) . . . . ? C3A C21A C22C C23C -172.46(11) . . . . ? S1A C21A C22C C23C -84.98(12) . . . . ? S1C C21A C22C C23C 16.22(10) . . . . ? C21A C22C C23C C24C -18.92(11) . . . . ? C22C C23C C24C S1C 13.17(10) . . . . ? C21A S1C C24C C23C -4.45(9) . . . . ? C14B N1B C1B O1B -2.0(4) . . . . ? C3B N1B C1B O1B -175.5(2) . . . . ? C14B N1B C1B C2B 177.4(2) . . . . ? C3B N1B C1B C2B 3.8(2) . . . . ? O1B C1B C2B C4B 55.6(3) . . . . ? N1B C1B C2B C4B -123.6(2) . . . . ? O1B C1B C2B C3B 175.6(3) . . . . ? N1B C1B C2B C3B -3.60(15) . . . . ? C1B N1B C3B C21B -122.7(2) . . . . ? C14B N1B C3B C21B 64.3(3) . . . . ? C1B N1B C3B C2B -3.8(2) . . . . ? C14B N1B C3B C2B -176.8(2) . . . . ? C1B C2B C3B N1B 3.33(14) . . . . ? C4B C2B C3B N1B 122.6(2) . . . . ? C1B C2B C3B C21B 119.7(2) . . . . ? C4B C2B C3B C21B -121.0(2) . . . . ? C6B N2B C4B C5B 134.6(2) . . . . ? C6B N2B C4B C2B -102.6(2) . . . . ? C1B C2B C4B N2B 43.0(2) . . . . ? C3B C2B C4B N2B -57.8(2) . . . . ? C1B C2B C4B C5B 165.6(2) . . . . ? C3B C2B C4B C5B 64.8(2) . . . . ? C4B N2B C6B O2B -1.4(3) . . . . ? C4B N2B C6B O3B 179.0(2) . . . . ? C7B O3B C6B O2B 6.9(3) . . . . ? C7B O3B C6B N2B -173.5(2) . . . . ? C6B O3B C7B C8B 173.0(2) . . . . ? O3B C7B C8B C13B 96.5(2) . . . . ? O3B C7B C8B C9B -82.6(3) . . . . ? C13B C8B C9B C10B -0.7(4) . . . . ? C7B C8B C9B C10B 178.4(3) . . . . ? C8B C9B C10B C11B -1.1(4) . . . . ? C9B C10B C11B C12B 1.2(5) . . . . ? C10B C11B C12B C13B 0.6(5) . . . . ? C11B C12B C13B C8B -2.6(4) . . . . ? C9B C8B C13B C12B 2.6(4) . . . . ? C7B C8B C13B C12B -176.5(2) . . . . ? C1B N1B C14B C15B -107.4(3) . . . . ? C3B N1B C14B C15B 63.6(3) . . . . ? N1B C14B C15B C16B 26.2(3) . . . . ? N1B C14B C15B C20B -158.7(2) . . . . ? C20B C15B C16B C17B 2.4(4) . . . . ? C14B C15B C16B C17B 177.4(3) . . . . ? C15B C16B C17B C18B 1.8(5) . . . . ? C16B C17B C18B C19B -5.3(5) . . . . ? C17B C18B C19B C20B 4.6(5) . . . . ? C16B C15B C20B C19B -3.1(4) . . . . ? C14B C15B C20B C19B -178.3(3) . . . . ? C18B C19B C20B C15B -0.4(5) . . . . ? N1B C3B C21B C22D -155.04(12) . . . . ? C2B C3B C21B C22D 105.2(2) . . . . ? N1B C3B C21B C22B 6.0(2) . . . . ? C2B C3B C21B C22B -93.8(2) . . . . ? N1B C3B C21B S1D 28.4(2) . . . . ? C2B C3B C21B S1D -71.4(2) . . . . ? N1B C3B C21B S1B -171.08(11) . . . . ? C2B C3B C21B S1B 89.1(2) . . . . ? C22D C21B S1B C24B 62.37(13) . . . . ? C22B C21B S1B C24B 4.85(6) . . . . ? C3B C21B S1B C24B -177.51(10) . . . . ? S1D C21B S1B C24B -14.97(6) . . . . ? C22D C21B C22B C23B -18.58(10) . . . . ? C3B C21B C22B C23B 176.59(12) . . . . ? S1D C21B C22B C23B 99.36(14) . . . . ? S1B C21B C22B C23B -6.05(10) . . . . ? C21B C22B C23B C24B 3.70(12) . . . . ? C22B C23B C24B S1B 0.44(10) . . . . ? C21B S1B C24B C23B -3.20(8) . . . . ? C22D C21B S1D C24D -1.74(6) . . . . ? C22B C21B S1D C24D -68.23(11) . . . . ? C3B C21B S1D C24D 175.37(10) . . . . ? S1B C21B S1D C24D 13.35(6) . . . . ? C22B C21B C22D C23D 23.03(9) . . . . ? C3B C21B C22D C23D -171.58(11) . . . . ? S1D C21B C22D C23D 5.39(9) . . . . ? S1B C21B C22D C23D -102.6(2) . . . . ? C21B C22D C23D C24D -6.63(10) . . . . ? C22D C23D C24D S1D 4.94(10) . . . . ? C21B S1D C24D C23D -1.98(8) . . . . ? _refine_diff_density_max 0.248 _refine_diff_density_min -0.194 _refine_diff_density_rms 0.057