# Supplementary Material (ESI) for Perkin Transactions # This journal is © The Royal Society of Chemistry 2000 # CCDC Number: 207/453 data_ah9605 _audit_creation_method SHELXL _chemical_name_systematic ; 3(S)-(Acetyl-amino)-8(R)-carboxy-azacane-2-one methy ester ; _chemical_name_common ? _chemical_formula_moiety ? _chemical_formula_structural ? _chemical_formula_analytical ? _chemical_formula_sum 'C11.50 H18.50 Cl1.50 N2 O4' _chemical_formula_weight 301.96 _chemical_melting_point ? _chemical_compound_source ? loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source 'C' 'C' 0.0181 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' 'Cl' 'Cl' 0.3639 0.7018 '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 7.955(2) _cell_length_b 18.210(5) _cell_length_c 10.141(2) _cell_angle_alpha 90.00 _cell_angle_beta 90.93(2) _cell_angle_gamma 90.00 _cell_volume 1468.8(6) _cell_formula_units_Z 4 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 22 _cell_measurement_theta_min 15 _cell_measurement_theta_max 75 _exptl_crystal_description ? _exptl_crystal_colour colourless _exptl_crystal_size_max 0.30 _exptl_crystal_size_mid 0.30 _exptl_crystal_size_min 0.25 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.365 _exptl_crystal_density_method ? _exptl_crystal_F_000 636 _exptl_absorpt_coefficient_mu 3.259 _exptl_absorpt_correction_type none _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _exptl_special_details ; Flack parameter 0.04(2) ; _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 AFC7R _diffrn_measurement_method 'omega 2theta scans' _diffrn_standards_number 3 _diffrn_standards_interval_count 200 _diffrn_standards_interval_time ? _diffrn_standards_decay_% 0% _diffrn_reflns_number 4894 _diffrn_reflns_av_R_equivalents 0.0266 _diffrn_reflns_av_sigmaI/netI 0.0390 _diffrn_reflns_limit_h_min -8 _diffrn_reflns_limit_h_max 8 _diffrn_reflns_limit_k_min -20 _diffrn_reflns_limit_k_max 20 _diffrn_reflns_limit_l_min -11 _diffrn_reflns_limit_l_max 11 _diffrn_reflns_theta_min 4.36 _diffrn_reflns_theta_max 60.06 _reflns_number_total 4375 _reflns_number_observed 3844 _reflns_observed_criterion >2sigma(I) _computing_data_collection ? _computing_cell_refinement ? _computing_data_reduction ? _computing_structure_solution 'SHELXS-86 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-93 (Sheldrick, 1993)' _computing_molecular_graphics ? _computing_publication_material ? _refine_special_details ; Refinement on F^2^ for ALL reflections except for 0 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^)+(0.0838P)^2^+0.3875P] 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 none _refine_ls_extinction_coef ? _refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _refine_ls_abs_structure_Flack 0.04(2) _refine_ls_number_reflns 4375 _refine_ls_number_parameters 372 _refine_ls_number_restraints 13 _refine_ls_R_factor_all 0.0588 _refine_ls_R_factor_obs 0.0513 _refine_ls_wR_factor_all 0.1419 _refine_ls_wR_factor_obs 0.1344 _refine_ls_goodness_of_fit_all 1.039 _refine_ls_goodness_of_fit_obs 1.055 _refine_ls_restrained_S_all 1.039 _refine_ls_restrained_S_obs 1.056 _refine_ls_shift/esd_max 0.029 _refine_ls_shift/esd_mean 0.004 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 C12 C 1.7654(6) 1.1304(3) 0.9907(6) 0.0794(14) Uani 0.47(2) d PD 1 H12A H 1.7602(6) 1.1721(3) 0.9296(6) 0.095 Uiso 0.47(2) calc PR 1 Cl1 Cl 1.6819(12) 1.0601(4) 0.8999(6) 0.101(2) Uani 0.47(2) d PD 1 Cl2 Cl 1.6449(12) 1.1577(6) 1.1157(9) 0.102(2) Uani 0.47(2) d PD 1 Cl3 Cl 1.9714(10) 1.1234(8) 1.0273(10) 0.127(3) Uani 0.47(2) d PD 1 C12' C 1.7654(6) 1.1304(3) 0.9907(6) 0.0794(14) Uani 0.53(2) d PD 2 H12B H 1.7120(14) 1.1638(5) 0.9269(13) 0.095 Uiso 0.53(2) calc PR 2 Cl1' Cl 1.7469(14) 1.0361(5) 0.9477(13) 0.120(4) Uani 0.53(2) d PD 2 Cl2' Cl 1.6761(19) 1.1348(8) 1.1547(15) 0.160(5) Uani 0.53(2) d PD 2 Cl3' Cl 1.9803(8) 1.1451(5) 1.0130(7) 0.101(2) Uani 0.53(2) d PD 2 O1 O 0.2630(3) 0.8493(2) -0.0479(2) 0.0568(7) Uani 1 d . . N1 N 0.0729(4) 0.8629(2) 0.1105(3) 0.0506(7) Uani 1 d . . H1A H -0.0027(4) 0.8584(2) 0.0494(3) 0.061 Uiso 1 calc R . C1 C 0.0917(6) 0.6878(3) 0.3781(5) 0.0695(12) Uani 1 d . . H1B H 0.0646(6) 0.6424(3) 0.3344(5) 0.104 Uiso 1 calc R . H1C H 0.0327(6) 0.6905(3) 0.4597(5) 0.104 Uiso 1 calc R . H1D H 0.2106(6) 0.6899(3) 0.3955(5) 0.104 Uiso 1 calc R . O2 O 0.4151(4) 0.7261(2) 0.2371(4) 0.0837(10) Uani 1 d . . N2 N 0.5175(3) 0.8250(2) 0.1363(3) 0.0459(7) Uani 1 d . . H2A H 0.5991(3) 0.8436(2) 0.0928(3) 0.055 Uiso 1 calc R . C2 C 0.2310(4) 0.8590(2) 0.0695(3) 0.0435(8) Uani 1 d . . O3 O 0.1319(4) 0.8287(2) 0.4470(3) 0.0660(8) Uani 1 d . . C3 C 0.3748(4) 0.8709(2) 0.1682(3) 0.0432(8) Uani 1 d . . H3A H 0.3366(4) 0.8589(2) 0.2571(3) 0.052 Uiso 1 calc R . O4 O 0.0426(4) 0.7486(2) 0.2948(3) 0.0634(8) Uani 1 d . . C4 C 0.4272(5) 0.9516(2) 0.1635(4) 0.0527(9) Uani 1 d . . H4A H 0.5182(5) 0.9595(2) 0.2267(4) 0.063 Uiso 1 calc R . H4B H 0.4697(5) 0.9624(2) 0.0765(4) 0.063 Uiso 1 calc R . C5 C 0.2858(6) 1.0049(2) 0.1933(5) 0.0621(10) Uani 1 d . . H5A H 0.2077(6) 1.0052(2) 0.1188(5) 0.075 Uiso 1 calc R . H5B H 0.3330(6) 1.0538(2) 0.2010(5) 0.075 Uiso 1 calc R . C6 C 0.1873(6) 0.9884(2) 0.3181(4) 0.0605(11) Uani 1 d . . H6A H 0.2558(6) 0.9570(2) 0.3747(4) 0.073 Uiso 1 calc R . H6B H 0.1702(6) 1.0342(2) 0.3649(4) 0.073 Uiso 1 calc R . C7 C 0.0168(5) 0.9516(2) 0.2971(4) 0.0592(10) Uani 1 d . . H7A H -0.0400(5) 0.9521(2) 0.3810(4) 0.071 Uiso 1 calc R . H7B H -0.0485(5) 0.9825(2) 0.2374(4) 0.071 Uiso 1 calc R . C8 C 0.0079(5) 0.8737(2) 0.2440(3) 0.0490(9) Uani 1 d . . H8A H -0.1128(5) 0.8638(2) 0.2347(3) 0.059 Uiso 1 calc R . C9 C 0.6771(6) 0.7125(3) 0.1282(6) 0.0765(14) Uani 1 d . . H9A H 0.7494(6) 0.7440(3) 0.0787(6) 0.115 Uiso 1 calc R . H9B H 0.6411(6) 0.6721(3) 0.0737(6) 0.115 Uiso 1 calc R . H9C H 0.7371(6) 0.6941(3) 0.2041(6) 0.115 Uiso 1 calc R . C10 C 0.0710(4) 0.8153(2) 0.3398(4) 0.0475(8) Uani 1 d . . C11 C 0.5255(5) 0.7553(2) 0.1720(4) 0.0546(10) Uani 1 d . . O1' O 0.7660(3) 0.8657(2) 0.9423(2) 0.0516(6) Uani 1 d . . N1' N 0.5720(4) 0.8536(2) 0.7811(3) 0.0524(8) Uani 1 d . . H1'A H 0.4978(4) 0.8541(2) 0.8418(3) 0.063 Uiso 1 calc R . C1' C 0.5846(7) 1.0368(3) 0.5344(6) 0.087(2) Uani 1 d . . H1'B H 0.5675(7) 1.0804(3) 0.5858(6) 0.130 Uiso 1 calc R . H1'C H 0.5128(7) 1.0382(3) 0.4574(6) 0.130 Uiso 1 calc R . H1'D H 0.6998(7) 1.0344(3) 0.5081(6) 0.130 Uiso 1 calc R . N2' N 1.0119(4) 0.9019(2) 0.7622(3) 0.0450(7) Uani 1 d . . H2'A H 1.0831(4) 0.8862(2) 0.8203(3) 0.054 Uiso 1 calc R . O2' O 0.9399(4) 0.9954(2) 0.6281(3) 0.0712(9) Uani 1 d . . C2' C 0.7312(4) 0.8594(2) 0.8227(3) 0.0444(8) Uani 1 d . . O3' O 0.6084(5) 0.8992(2) 0.4449(3) 0.0788(9) Uani 1 d . . C3' C 0.8734(4) 0.8543(2) 0.7237(3) 0.0406(7) Uani 1 d . . H3'A H 0.8312(4) 0.8687(2) 0.6361(3) 0.049 Uiso 1 calc R . O4' O 0.5449(4) 0.9732(2) 0.6121(3) 0.0724(9) Uani 1 d . . C4' C 0.9327(5) 0.7756(2) 0.7200(4) 0.0504(9) Uani 1 d . . H4'A H 1.0216(5) 0.7718(2) 0.6559(4) 0.061 Uiso 1 calc R . H4'B H 0.9812(5) 0.7634(2) 0.8056(4) 0.061 Uiso 1 calc R . C5' C 0.7999(6) 0.7191(2) 0.6860(4) 0.0611(11) Uani 1 d . . H5'A H 0.7251(6) 0.7143(2) 0.7602(4) 0.073 Uiso 1 calc R . H5'B H 0.8543(6) 0.6720(2) 0.6735(4) 0.073 Uiso 1 calc R . C6' C 0.6934(6) 0.7372(3) 0.5609(4) 0.0643(11) Uani 1 d . . H6'A H 0.7566(6) 0.7711(3) 0.5070(4) 0.077 Uiso 1 calc R . H6'B H 0.6782(6) 0.6924(3) 0.5104(4) 0.077 Uiso 1 calc R . C7' C 0.5203(5) 0.7705(3) 0.5852(4) 0.0634(11) Uani 1 d . . H7'A H 0.4604(5) 0.7717(3) 0.5012(4) 0.076 Uiso 1 calc R . H7'B H 0.4601(5) 0.7368(3) 0.6414(4) 0.076 Uiso 1 calc R . C8' C 0.5063(5) 0.8466(2) 0.6462(4) 0.0562(10) Uani 1 d . . H8'A H 0.3850(5) 0.8543(2) 0.6546(4) 0.067 Uiso 1 calc R . C9' C 1.1840(6) 1.0104(3) 0.7627(5) 0.0683(12) Uani 1 d . . H9'A H 1.2427(6) 0.9812(3) 0.8275(5) 0.102 Uiso 1 calc R . H9'B H 1.1479(6) 1.0555(3) 0.8022(5) 0.102 Uiso 1 calc R . H9'C H 1.2576(6) 1.0210(3) 0.6911(5) 0.102 Uiso 1 calc R . C10' C 0.5617(5) 0.9079(3) 0.5558(4) 0.0585(10) Uani 1 d . . C11' C 1.0341(5) 0.9689(2) 0.7119(4) 0.0478(9) 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 C12 0.070(3) 0.078(3) 0.091(3) -0.009(3) 0.013(3) 0.001(2) Cl1 0.130(4) 0.077(3) 0.097(3) -0.003(2) 0.003(3) -0.012(3) Cl2 0.092(3) 0.120(5) 0.096(3) -0.022(3) 0.032(3) 0.008(3) Cl3 0.065(4) 0.143(7) 0.174(6) 0.008(4) -0.015(3) 0.034(4) C12' 0.070(3) 0.078(3) 0.091(3) -0.009(3) 0.013(3) 0.001(2) Cl1' 0.125(5) 0.092(4) 0.145(6) -0.049(4) 0.058(5) -0.049(4) Cl2' 0.178(9) 0.143(8) 0.164(8) -0.059(6) 0.116(7) -0.043(5) Cl3' 0.079(3) 0.110(4) 0.116(3) -0.047(3) 0.034(3) -0.032(3) O1 0.0420(13) 0.088(2) 0.0405(14) -0.0040(13) -0.0013(10) 0.0078(14) N1 0.033(2) 0.075(2) 0.043(2) 0.001(2) -0.0017(12) 0.002(2) C1 0.071(3) 0.059(3) 0.079(3) 0.010(2) 0.012(2) -0.002(2) O2 0.067(2) 0.068(2) 0.118(3) 0.013(2) 0.030(2) 0.000(2) N2 0.0313(15) 0.062(2) 0.044(2) 0.0077(14) 0.0038(12) 0.0065(14) C2 0.037(2) 0.055(2) 0.038(2) 0.002(2) -0.0003(13) 0.003(2) O3 0.086(2) 0.067(2) 0.045(2) 0.0065(13) -0.0011(14) -0.004(2) C3 0.035(2) 0.059(2) 0.035(2) 0.002(2) -0.0002(13) 0.006(2) O4 0.062(2) 0.060(2) 0.067(2) -0.0029(14) -0.0060(14) -0.0016(14) C4 0.045(2) 0.062(2) 0.051(2) 0.005(2) -0.001(2) -0.002(2) C5 0.063(3) 0.050(2) 0.073(3) 0.008(2) 0.010(2) 0.000(2) C6 0.062(3) 0.051(2) 0.069(3) -0.008(2) 0.005(2) 0.005(2) C7 0.052(2) 0.068(3) 0.058(2) 0.004(2) 0.011(2) 0.016(2) C8 0.035(2) 0.066(2) 0.046(2) 0.000(2) 0.0065(15) 0.002(2) C9 0.053(3) 0.071(3) 0.106(4) -0.002(3) 0.004(2) 0.012(2) C10 0.034(2) 0.059(2) 0.050(2) 0.001(2) 0.010(2) 0.000(2) C11 0.040(2) 0.065(3) 0.059(2) 0.002(2) 0.000(2) 0.000(2) O1' 0.0413(13) 0.077(2) 0.0366(13) -0.0007(12) 0.0031(10) -0.0007(13) N1' 0.035(2) 0.077(2) 0.045(2) -0.001(2) 0.0037(12) -0.003(2) C1' 0.083(4) 0.066(3) 0.111(4) 0.015(3) -0.018(3) 0.005(3) N2' 0.035(2) 0.060(2) 0.0400(15) 0.0052(14) -0.0030(12) -0.0050(14) O2' 0.072(2) 0.058(2) 0.084(2) 0.016(2) -0.014(2) 0.000(2) C2' 0.037(2) 0.052(2) 0.044(2) 0.002(2) 0.0009(14) -0.001(2) O3' 0.096(3) 0.094(2) 0.046(2) 0.013(2) -0.008(2) -0.006(2) C3' 0.036(2) 0.051(2) 0.035(2) 0.002(2) 0.0034(13) -0.002(2) O4' 0.063(2) 0.070(2) 0.084(2) -0.001(2) 0.003(2) 0.003(2) C4' 0.050(2) 0.053(2) 0.048(2) 0.001(2) 0.008(2) 0.002(2) C5' 0.065(3) 0.052(2) 0.066(3) 0.003(2) 0.006(2) -0.004(2) C6' 0.067(3) 0.061(3) 0.065(3) -0.014(2) -0.001(2) -0.011(2) C7' 0.054(2) 0.077(3) 0.059(3) -0.001(2) -0.005(2) -0.022(2) C8' 0.038(2) 0.081(3) 0.050(2) 0.001(2) -0.0046(15) -0.006(2) C9' 0.050(2) 0.064(3) 0.091(3) -0.004(2) 0.009(2) -0.010(2) C10' 0.046(2) 0.075(3) 0.054(2) 0.002(2) -0.017(2) 0.001(2) C11' 0.042(2) 0.051(2) 0.050(2) -0.004(2) 0.009(2) 0.004(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 C12 Cl2 1.678(10) . ? C12 Cl3 1.679(8) . ? C12 Cl1 1.706(8) . ? C12' Cl3' 1.741(8) . ? C12' Cl1' 1.778(8) . ? C12' Cl2' 1.821(11) . ? O1 C2 1.234(4) . ? N1 C2 1.333(5) . ? N1 C8 1.470(5) . ? C1 O4 1.443(5) . ? O2 C11 1.229(5) . ? N2 C11 1.320(5) . ? N2 C3 1.451(5) . ? C2 C3 1.523(5) . ? O3 C10 1.208(5) . ? C3 C4 1.528(6) . ? O4 C10 1.316(5) . ? C4 C5 1.519(6) . ? C5 C6 1.530(6) . ? C6 C7 1.525(6) . ? C7 C8 1.520(6) . ? C8 C10 1.520(5) . ? C9 C11 1.509(6) . ? O1' C2' 1.245(4) . ? N1' C2' 1.332(5) . ? N1' C8' 1.462(5) . ? C1' O4' 1.439(6) . ? N2' C11' 1.336(5) . ? N2' C3' 1.450(5) . ? O2' C11' 1.223(5) . ? C2' C3' 1.527(5) . ? O3' C10' 1.201(5) . ? C3' C4' 1.510(5) . ? O4' C10' 1.327(6) . ? C4' C5' 1.510(6) . ? C5' C6' 1.550(6) . ? C6' C7' 1.528(6) . ? C7' C8' 1.523(7) . ? C8' C10' 1.514(6) . ? C9' C11' 1.495(6) . ? 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 Cl2 C12 Cl3 115.0(6) . . ? Cl2 C12 Cl1 114.1(5) . . ? Cl3 C12 Cl1 115.6(5) . . ? Cl3' C12' Cl1' 104.9(4) . . ? Cl3' C12' Cl2' 105.7(6) . . ? Cl1' C12' Cl2' 103.5(7) . . ? C2 N1 C8 129.9(3) . . ? C11 N2 C3 121.8(3) . . ? O1 C2 N1 121.2(3) . . ? O1 C2 C3 119.4(3) . . ? N1 C2 C3 119.3(3) . . ? N2 C3 C2 110.7(3) . . ? N2 C3 C4 109.5(3) . . ? C2 C3 C4 108.6(3) . . ? C10 O4 C1 117.5(3) . . ? C5 C4 C3 113.8(3) . . ? C4 C5 C6 115.5(4) . . ? C7 C6 C5 115.9(4) . . ? C8 C7 C6 119.7(3) . . ? N1 C8 C10 112.2(3) . . ? N1 C8 C7 115.8(3) . . ? C10 C8 C7 114.5(3) . . ? O3 C10 O4 124.3(4) . . ? O3 C10 C8 123.9(4) . . ? O4 C10 C8 111.8(3) . . ? O2 C11 N2 122.2(4) . . ? O2 C11 C9 121.0(4) . . ? N2 C11 C9 116.8(4) . . ? C2' N1' C8' 128.8(3) . . ? C11' N2' C3' 123.2(3) . . ? O1' C2' N1' 120.7(3) . . ? O1' C2' C3' 119.4(3) . . ? N1' C2' C3' 119.8(3) . . ? N2' C3' C4' 109.7(3) . . ? N2' C3' C2' 110.8(3) . . ? C4' C3' C2' 108.0(3) . . ? C10' O4' C1' 117.5(4) . . ? C5' C4' C3' 115.8(3) . . ? C4' C5' C6' 114.4(4) . . ? C7' C6' C5' 115.7(4) . . ? C8' C7' C6' 119.9(3) . . ? N1' C8' C10' 113.5(3) . . ? N1' C8' C7' 115.6(4) . . ? C10' C8' C7' 113.6(3) . . ? O3' C10' O4' 123.8(4) . . ? O3' C10' C8' 124.5(4) . . ? O4' C10' C8' 111.6(4) . . ? O2' C11' N2' 122.8(4) . . ? O2' C11' C9' 121.1(4) . . ? N2' C11' C9' 116.0(4) . . ? _refine_diff_density_max 0.141 _refine_diff_density_min -0.173 _refine_diff_density_rms 0.038