Supplementary Material (ESI) for Perkin Transactions This journal is © The Royal Society of Chemistry 2001 data_global _journal_coden_Cambridge 207 _publ_requested_journal 'Perkin Transactions 1' _audit_creation_method SHELXL-97 # SUBMISSION DETAILS _publ_contact_author ; Prof T Gallagher School of Chemistry University of Bristol Bristol BS8 1TS UNITED KINGDOM ; _publ_contact_letter ; Please consider this CIF submission for publication in Perkin Transactions ; # TITLE AND AUTHOR LIST _publ_section_title ; The Azomethine Ylid Strategy for \b-Lactam Synthesis. An Exploration of Alternative Pathways ; loop_ _publ_author_name _publ_author_address 'Giles A. Brown' ; School of Chemistry University of Bristol Bristol BS8 1TS UK ; 'Jonathan P.H. Charmant' ; School of Chemistry University of Bristol Bristol BS8 1TS UK ; 'Sarah R. Martel' ; School of Chemistry University of Bristol Bristol BS8 1TS UK ; 'Richard Wisedale' ; School of Chemistry University of Bristol Bristol BS8 1TS UK ; 'Timothy Gallagher' ; School of Chemistry University of Bristol Bristol BS8 1TS UK ; 'Neil J. Halesb' ; School of Chemistry University of Bristol Bristol BS8 1TS UK ; 'Colin W. G. Fishwick' ; School of Chemistry University of Bristol Bristol BS8 1TS UK ; ######################################################################### data_bradgate _database_code_CSD 155747 _audit_creation_method SHELXL _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_formula_moiety ? _chemical_formula_structural ? _chemical_formula_analytical ? _chemical_formula_sum 'C21 H35 N3 O9' _chemical_formula_weight 473.52 _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' 0.0033 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 Triclinic _symmetry_space_group_name_H-M P-1 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 8.014(4) _cell_length_b 8.438(4) _cell_length_c 18.463(10) _cell_angle_alpha 89.99(2) _cell_angle_beta 82.22(4) _cell_angle_gamma 78.06(4) _cell_volume 1209.8(10) _cell_formula_units_Z 2 _cell_measurement_temperature 173(2) _cell_measurement_reflns_used 42 _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description plate _exptl_crystal_colour colourless _exptl_crystal_size_max 0.3 _exptl_crystal_size_mid 0.2 _exptl_crystal_size_min 0.02 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.300 _exptl_crystal_density_method none _exptl_crystal_F_000 508 _exptl_absorpt_coefficient_mu 0.102 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.826 _exptl_absorpt_correction_T_max 1.000 _exptl_absorpt_process_details ; G. M. Sheldrick. SADABS: A program for absorption correction with the Siemens SMART system; University of G\"ottingen: Germany, 1996. ; _exptl_special_details ; ? ; _diffrn_ambient_temperature 173(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 'CCD area-detector' _diffrn_measurement_method '\w scans' _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% none _diffrn_reflns_number 10221 _diffrn_reflns_av_R_equivalents 0.0409 _diffrn_reflns_av_sigmaI/netI 0.0644 _diffrn_reflns_limit_h_min -10 _diffrn_reflns_limit_h_max 10 _diffrn_reflns_limit_k_min -10 _diffrn_reflns_limit_k_max 10 _diffrn_reflns_limit_l_min -23 _diffrn_reflns_limit_l_max 23 _diffrn_reflns_theta_min 2.23 _diffrn_reflns_theta_max 25.00 _reflns_number_total 4224 _reflns_number_observed 2719 _reflns_observed_criterion >2sigma(I) _computing_data_collection 'Bruker SHELXTL' _computing_cell_refinement 'Bruker SHELXTL' _computing_data_reduction 'Bruker SHELXTL' _computing_structure_solution 'SHELXS-86 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-93 (Sheldrick, 1993)' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _refine_special_details ; Refinement on F^2^ for ALL reflections except for 3 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 _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0455P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment mixed _refine_ls_extinction_method SHELXL _refine_ls_extinction_coef 0.0203(20) _refine_ls_extinction_expression 'Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^' _refine_ls_number_reflns 4221 _refine_ls_number_parameters 327 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0828 _refine_ls_R_factor_obs 0.0429 _refine_ls_wR_factor_all 0.1008 _refine_ls_wR_factor_obs 0.0862 _refine_ls_goodness_of_fit_all 0.965 _refine_ls_goodness_of_fit_obs 1.053 _refine_ls_restrained_S_all 0.967 _refine_ls_restrained_S_obs 1.053 _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 0.1092(2) -1.2732(2) 0.18761(9) 0.0213(4) Uani 1 d . . C2 C -0.0328(2) -1.2490(2) 0.14303(11) 0.0234(5) Uani 1 d . . H2 H -0.0397(2) -1.1464(2) 0.11545(11) 0.028 Uiso 1 calc R . C3 C 0.0691(3) -1.3966(2) 0.09517(11) 0.0253(5) Uani 1 d . . H3A H 0.0140(3) -1.4916(2) 0.09776(11) 0.030 Uiso 1 calc R . H3B H 0.1064(3) -1.3711(2) 0.04393(11) 0.030 Uiso 1 calc R . C4 C 0.2049(3) -1.4024(3) 0.14553(11) 0.0245(5) Uani 1 d . . O4 O 0.3474(2) -1.4832(2) 0.14905(8) 0.0371(4) Uani 1 d . . C5 C 0.1631(2) -1.1654(2) 0.23592(11) 0.0226(5) Uani 1 d . . C6 C 0.2118(3) -1.0279(2) 0.20549(11) 0.0235(5) Uani 1 d . . O6 O 0.2117(2) -0.9998(2) 0.13739(7) 0.0287(4) Uani 1 d . . C7 C 0.2570(3) -0.8987(3) 0.25192(12) 0.0334(6) Uani 1 d . . H7A H 0.3162(3) -0.9503(3) 0.29227(12) 0.040 Uiso 1 calc R . H7B H 0.3366(3) -0.8418(3) 0.22165(12) 0.040 Uiso 1 calc R . C8 C 0.0959(4) -0.7773(3) 0.2834(2) 0.0671(9) Uani 1 d . . H8A H 0.1286(4) -0.6859(11) 0.3066(9) 0.101 Uiso 1 calc R . H8B H 0.0263(12) -0.8297(7) 0.3198(7) 0.101 Uiso 1 calc R . H8C H 0.0288(13) -0.7377(17) 0.2440(2) 0.101 Uiso 1 calc R . C9 C 0.1688(3) -1.2098(3) 0.31103(12) 0.0274(5) Uani 1 d . . O9 O 0.2134(2) -1.1356(2) 0.35919(8) 0.0459(5) Uani 1 d . . O10 O 0.1206(2) -1.3549(2) 0.32559(7) 0.0284(4) Uani 1 d . . C11 C 0.1174(3) -1.4016(3) 0.40156(11) 0.0308(5) Uani 1 d . . H11A H 0.2055(3) -1.3585(3) 0.42358(11) 0.037 Uiso 1 calc R . H11B H 0.1455(3) -1.5212(3) 0.40390(11) 0.037 Uiso 1 calc R . C12 C -0.0570(3) -1.3371(3) 0.44410(11) 0.0286(5) Uani 1 d . . C13 C -0.0848(3) -1.2098(3) 0.49505(11) 0.0314(6) Uani 1 d . . H13 H 0.0086(3) -1.1618(3) 0.50319(11) 0.038 Uiso 1 calc R . C14 C -0.1952(3) -1.4061(3) 0.43265(11) 0.0322(6) Uani 1 d . . H14 H -0.1772(3) -1.4938(3) 0.39830(11) 0.039 Uiso 1 calc R . C15 C -0.2460(3) -1.1517(3) 0.53410(12) 0.0339(6) Uani 1 d . . H15 H -0.2643(3) -1.0647(3) 0.56886(12) 0.041 Uiso 1 calc R . C16 C -0.3580(3) -1.3493(3) 0.47028(12) 0.0343(6) Uani 1 d . . H16 H -0.4524(3) -1.3950(3) 0.46150(12) 0.041 Uiso 1 calc R . C17 C -0.3794(3) -1.2235(3) 0.52124(12) 0.0315(5) Uani 1 d . . N17 N -0.5514(3) -1.1651(3) 0.56332(11) 0.0417(5) Uani 1 d . . O17A O -0.5745(2) -1.0432(2) 0.60251(9) 0.0522(5) Uani 1 d . . O17B O -0.6640(2) -1.2410(2) 0.55719(11) 0.0664(6) Uani 1 d . . N18 N -0.2076(2) -1.2596(2) 0.18520(9) 0.0233(4) Uani 1 d . . C19 C -0.1977(3) -1.4226(2) 0.22169(11) 0.0264(5) Uani 1 d . . H19A H -0.1099(3) -1.4342(2) 0.25534(11) 0.032 Uiso 1 calc R . H19B H -0.1577(3) -1.5095(2) 0.18349(11) 0.032 Uiso 1 calc R . C20 C -0.3659(3) -1.4483(3) 0.26454(12) 0.0352(6) Uani 1 d . . H20A H -0.3470(5) -1.5554(7) 0.2863(6) 0.053 Uiso 1 calc R . H20B H -0.4529(6) -1.4415(16) 0.2315(2) 0.053 Uiso 1 calc R . H20C H -0.4058(9) -1.3646(10) 0.3034(5) 0.053 Uiso 1 calc R . C21 C -0.3428(3) -1.2324(3) 0.13269(12) 0.0324(6) Uani 1 d . . H21A H -0.4571(3) -1.2295(3) 0.16141(12) 0.039 Uiso 1 calc R . H21B H -0.3455(3) -1.1248(3) 0.11099(12) 0.039 Uiso 1 calc R . C22 C -0.3154(3) -1.3578(3) 0.07107(12) 0.0405(6) Uani 1 d . . H22A H -0.2117(11) -1.3503(12) 0.0375(4) 0.061 Uiso 1 calc R . H22B H -0.4153(9) -1.3377(11) 0.0445(5) 0.061 Uiso 1 calc R . H22C H -0.3015(18) -1.4663(3) 0.09136(14) 0.061 Uiso 1 calc R . C23 C -0.2596(3) -1.1269(2) 0.24466(12) 0.0296(5) Uani 1 d . . H23A H -0.3769(3) -1.1300(2) 0.26885(12) 0.036 Uiso 1 calc R . H23B H -0.1807(3) -1.1522(2) 0.28190(12) 0.036 Uiso 1 calc R . C24 C -0.2590(3) -0.9561(3) 0.21990(13) 0.0380(6) Uani 1 d . . H24A H -0.2962(17) -0.8804(3) 0.2620(2) 0.057 Uiso 1 calc R . H24B H -0.3380(13) -0.9281(6) 0.1836(6) 0.057 Uiso 1 calc R . H24C H -0.1423(5) -0.9491(5) 0.1981(7) 0.057 Uiso 1 calc R . O25 O -0.0387(3) -0.7431(2) 0.08794(10) 0.0423(5) Uani 1 d . . H25X H 0.0418(41) -0.8156(39) 0.1001(18) 0.088(12) Uiso 1 d . . H25Y H -0.0988(37) -0.8005(35) 0.0614(16) 0.078(10) Uiso 1 d . . O26 O 0.4478(2) -0.8049(3) 0.08373(9) 0.0405(5) Uani 1 d . . H26X H 0.4129(36) -0.7068(38) 0.1006(16) 0.071(11) Uiso 1 d . . H26Y H 0.3640(39) -0.8588(35) 0.1007(16) 0.079(10) Uiso 1 d . . O27 O 0.2310(2) -1.0988(3) -0.01098(12) 0.0536(6) Uani 1 d . . H27X H 0.3470(47) -1.1256(39) -0.0360(18) 0.104(12) Uiso 1 d . . H27Y H 0.2322(37) -1.0667(36) 0.0310(18) 0.076(11) Uiso 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 N1 0.0222(9) 0.0202(10) 0.0214(10) -0.0015(8) -0.0044(7) -0.0035(8) C2 0.0239(12) 0.0245(12) 0.0224(12) 0.0012(9) -0.0028(9) -0.0064(10) C3 0.0285(12) 0.0296(13) 0.0180(11) -0.0040(9) 0.0006(9) -0.0091(10) C4 0.0233(12) 0.0248(12) 0.0254(12) -0.0040(10) 0.0009(10) -0.0080(10) O4 0.0239(9) 0.0341(10) 0.0504(11) -0.0125(8) -0.0055(7) 0.0007(7) C5 0.0255(12) 0.0227(12) 0.0204(11) -0.0021(9) -0.0039(9) -0.0065(10) C6 0.0226(11) 0.0249(12) 0.0221(12) -0.0008(9) -0.0024(9) -0.0032(9) O6 0.0357(9) 0.0300(9) 0.0221(9) 0.0013(7) -0.0038(7) -0.0109(7) C7 0.0484(15) 0.0280(13) 0.0281(13) 0.0005(10) -0.0064(11) -0.0171(12) C8 0.089(2) 0.039(2) 0.071(2) -0.027(2) -0.044(2) 0.014(2) C9 0.0307(13) 0.0249(13) 0.0262(13) -0.0001(10) -0.0017(10) -0.0062(10) O9 0.0841(13) 0.0399(10) 0.0253(9) 0.0015(8) -0.0176(9) -0.0334(10) O10 0.0421(9) 0.0257(9) 0.0202(8) 0.0046(7) -0.0049(7) -0.0127(7) C11 0.0462(14) 0.0271(13) 0.0211(12) 0.0085(10) -0.0090(10) -0.0097(11) C12 0.0436(14) 0.0263(13) 0.0185(12) 0.0053(10) -0.0055(10) -0.0121(11) C13 0.0446(15) 0.0282(13) 0.0262(13) 0.0048(10) -0.0106(11) -0.0150(11) C14 0.051(2) 0.0290(13) 0.0203(12) -0.0006(10) -0.0065(11) -0.0163(12) C15 0.053(2) 0.0260(13) 0.0255(13) -0.0011(10) -0.0087(12) -0.0114(12) C16 0.0458(15) 0.0345(14) 0.0278(13) 0.0038(11) -0.0075(11) -0.0186(12) C17 0.0419(14) 0.0300(13) 0.0232(12) 0.0053(10) -0.0031(10) -0.0098(11) N17 0.0494(14) 0.0402(13) 0.0347(12) 0.0031(10) -0.0024(10) -0.0101(11) O17A 0.0578(12) 0.0489(12) 0.0445(11) -0.0132(9) -0.0023(9) -0.0020(9) O17B 0.0535(12) 0.0620(14) 0.085(2) -0.0117(11) 0.0097(11) -0.0270(11) N18 0.0227(10) 0.0237(10) 0.0227(10) 0.0022(8) -0.0036(8) -0.0027(8) C19 0.0296(12) 0.0246(12) 0.0261(12) 0.0076(10) -0.0067(10) -0.0061(10) C20 0.0330(13) 0.0422(15) 0.0336(14) 0.0096(11) -0.0061(11) -0.0143(12) C21 0.0257(12) 0.0389(14) 0.0335(14) 0.0110(11) -0.0112(10) -0.0039(11) C22 0.0349(14) 0.058(2) 0.0322(14) 0.0007(12) -0.0130(11) -0.0119(13) C23 0.0269(12) 0.0285(13) 0.0295(13) -0.0025(10) 0.0028(10) -0.0014(10) C24 0.0389(14) 0.0261(14) 0.045(2) -0.0030(11) 0.0000(12) -0.0013(11) O25 0.0465(12) 0.0317(11) 0.0528(12) 0.0026(9) -0.0179(9) -0.0104(10) O26 0.0383(11) 0.0366(12) 0.0429(11) -0.0028(9) 0.0091(8) -0.0090(9) O27 0.0395(12) 0.082(2) 0.0395(12) -0.0251(11) -0.0004(9) -0.0172(10) _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 C4 1.369(3) . ? N1 C5 1.441(2) . ? N1 C2 1.474(2) . ? C2 N18 1.527(3) . ? C2 C3 1.544(3) . ? C3 C4 1.518(3) . ? C4 O4 1.213(2) . ? C5 C6 1.393(3) . ? C5 C9 1.441(3) . ? C6 O6 1.280(2) . ? C6 C7 1.518(3) . ? C7 C8 1.518(3) . ? C9 O9 1.220(2) . ? C9 O10 1.374(2) . ? O10 C11 1.455(2) . ? C11 C12 1.501(3) . ? C12 C13 1.391(3) . ? C12 C14 1.393(3) . ? C13 C15 1.384(3) . ? C14 C16 1.382(3) . ? C15 C17 1.380(3) . ? C16 C17 1.386(3) . ? C17 N17 1.475(3) . ? N17 O17A 1.225(2) . ? N17 O17B 1.227(2) . ? N18 C23 1.522(3) . ? N18 C19 1.523(3) . ? N18 C21 1.532(3) . ? C19 C20 1.524(3) . ? C21 C22 1.516(3) . ? C23 C24 1.512(3) . ? 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 C4 N1 C5 129.7(2) . . ? C4 N1 C2 93.8(2) . . ? C5 N1 C2 132.0(2) . . ? N1 C2 N18 114.5(2) . . ? N1 C2 C3 87.89(15) . . ? N18 C2 C3 118.4(2) . . ? C4 C3 C2 85.40(15) . . ? O4 C4 N1 131.0(2) . . ? O4 C4 C3 136.1(2) . . ? N1 C4 C3 92.9(2) . . ? C6 C5 C9 124.8(2) . . ? C6 C5 N1 117.1(2) . . ? C9 C5 N1 118.1(2) . . ? O6 C6 C5 121.6(2) . . ? O6 C6 C7 116.4(2) . . ? C5 C6 C7 121.9(2) . . ? C8 C7 C6 110.6(2) . . ? O9 C9 O10 120.0(2) . . ? O9 C9 C5 127.3(2) . . ? O10 C9 C5 112.6(2) . . ? C9 O10 C11 114.62(15) . . ? O10 C11 C12 110.5(2) . . ? C13 C12 C14 118.8(2) . . ? C13 C12 C11 121.7(2) . . ? C14 C12 C11 119.5(2) . . ? C15 C13 C12 121.2(2) . . ? C16 C14 C12 121.3(2) . . ? C17 C15 C13 118.3(2) . . ? C14 C16 C17 118.0(2) . . ? C15 C17 C16 122.5(2) . . ? C15 C17 N17 119.0(2) . . ? C16 C17 N17 118.5(2) . . ? O17A N17 O17B 123.4(2) . . ? O17A N17 C17 118.3(2) . . ? O17B N17 C17 118.3(2) . . ? C23 N18 C19 108.2(2) . . ? C23 N18 C2 109.33(15) . . ? C19 N18 C2 110.5(2) . . ? C23 N18 C21 108.3(2) . . ? C19 N18 C21 111.40(15) . . ? C2 N18 C21 109.1(2) . . ? N18 C19 C20 115.2(2) . . ? C22 C21 N18 115.7(2) . . ? C24 C23 N18 116.1(2) . . ? _refine_diff_density_max 0.165 _refine_diff_density_min -0.242 _refine_diff_density_rms 0.040