# Supplementary Material (ESI) for Perkin Transactions # This journal is © The Royal Society of Chemistry 2001 data_global #============================================================================== _journal_coden_Cambridge 207 # 1. SUBMISSION DETAILS _publ_contact_author ; Prof. T. Gallagher, School of Chemistry, Cantocks Close, University of Bristol. Bristol. BS8 1TS. ; _publ_contact_author_phone '0117 928 8260' _publ_contact_author_fax '0117 929 8611' _publ_contact_author_email 'T.Gallagher@bris.ac.uk' _publ_requested_journal 'J. Chem. Soc. Perkin Trans. 1' _publ_requested_coeditor_name ? _publ_contact_letter ; ; #============================================================================== # 2. PROCESSING SUMMARY (IUCr Office Use Only) _journal_coden_ASTM ? _journal_name_full ? _journal_year ? _journal_volume ? _journal_issue ? _journal_page_first ? _journal_page_last ? _journal_suppl_publ_number ? _journal_suppl_publ_pages ? #============================================================================== # 3. TITLE AND AUTHOR LIST _publ_section_title ; Trapping Highly Reactive Dipolarophiles. Exploiting the Mechanism Associated with the Azomethine Ylide Strategy for b-Lactam Synthesis. ; # The loop structure below should contain the names and addresses of all # authors, in the required order of publication. Repeat as necessary. loop_ _publ_author_name _publ_author_address 'Brown, Giles A.' ; School of Chemistry University of Bristol Cantocks Close BS8 1TS. Bristol, UK ; 'Anderson, Kirsty M.' ; School of Chemistry University of Bristol Cantocks Close BS8 1TS. Bristol, UK ; 'Large, Jonathan M.' ; School of Chemistry University of Bristol Cantocks Close BS8 1TS. Bristol, UK ; 'Planchenault Denis' ; School of Chemistry University of Bristol Cantocks Close BS8 1TS. Bristol, UK ; 'Urban, Dominique' ; School of Chemistry University of Bristol Cantocks Close BS8 1TS. Bristol, UK ; 'Hales, Neil J.' ; AstraZeneca Mereside Alderley Park SK10 4TG. Macclesfield, UK ; 'Gallagher, Timothy' ; School of Chemistry University of Bristol Cantocks Close BS8 1TS. Bristol, UK ; #============================================================================== # 4. TEXT data_8a _database_code_CSD 163810 _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C19 H16 N2 O5 S' _chemical_formula_weight 384.40 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source 'C' 'C' 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 'H' 'H' 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 'N' 'N' 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 'O' 'O' 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 'S' 'S' 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Monoclinic _symmetry_space_group_name_H-M P2(1)/n loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, y+1/2, -z+1/2' '-x, -y, -z' 'x-1/2, -y-1/2, z-1/2' _cell_length_a 5.713(2) _cell_length_b 31.811(12) _cell_length_c 9.900(4) _cell_angle_alpha 90.00 _cell_angle_beta 98.246(9) _cell_angle_gamma 90.00 _cell_volume 1780.6(11) _cell_formula_units_Z 4 _cell_measurement_temperature 173(2) _cell_measurement_reflns_used 40 _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description plate _exptl_crystal_colour colourless _exptl_crystal_size_max 0.4 _exptl_crystal_size_mid 0.2 _exptl_crystal_size_min 0.01 _exptl_crystal_density_meas 'not measured' _exptl_crystal_density_diffrn 1.434 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 800 _exptl_absorpt_coefficient_mu 0.216 _exptl_absorpt_correction_type none _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _exptl_absorpt_process_details ? _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_type 'Siemens CCD area detector' _diffrn_measurement_method '\w scans with narrow frames' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% none _diffrn_reflns_number 9553 _diffrn_reflns_av_R_equivalents 0.2446 _diffrn_reflns_av_sigmaI/netI 0.2501 _diffrn_reflns_limit_h_min -5 _diffrn_reflns_limit_h_max 6 _diffrn_reflns_limit_k_min -37 _diffrn_reflns_limit_k_max 37 _diffrn_reflns_limit_l_min -10 _diffrn_reflns_limit_l_max 11 _diffrn_reflns_theta_min 2.17 _diffrn_reflns_theta_max 25.00 _reflns_number_total 3136 _reflns_number_gt 1275 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SMART' _computing_data_reduction 'Bruker SHELXTL' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0313P)^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 constr _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 3136 _refine_ls_number_parameters 244 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.1992 _refine_ls_R_factor_gt 0.0707 _refine_ls_wR_factor_ref 0.1635 _refine_ls_wR_factor_gt 0.1204 _refine_ls_goodness_of_fit_ref 0.911 _refine_ls_restrained_S_all 0.911 _refine_ls_shift/su_max 0.001 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group S1 S -0.9221(3) 0.73401(4) 1.14142(16) 0.0368(5) Uani 1 1 d . . . N2 N -0.0218(15) 0.4985(2) 0.7161(10) 0.077(3) Uani 1 1 d . . . N4 N -0.7172(8) 0.76473(13) 0.9382(4) 0.0289(12) Uani 1 1 d . . . O1 O -0.4176(7) 0.81699(12) 0.9728(4) 0.0412(11) Uani 1 1 d . . . O2 O -0.9455(9) 0.69589(13) 0.8115(5) 0.0510(12) Uani 1 1 d . . . O3 O -0.6025(7) 0.66036(10) 0.8340(4) 0.0357(11) Uani 1 1 d . . . O4 O -0.0513(11) 0.47536(15) 0.6133(6) 0.092(2) Uani 1 1 d . . . O5 O 0.1370(12) 0.49525(19) 0.8092(9) 0.102(3) Uani 1 1 d . . . C2 C -0.6361(9) 0.71146(15) 1.1122(5) 0.0244(14) Uani 1 1 d . . . H2A H -0.5107 0.7261 1.1721 0.029 Uiso 1 1 calc R . . C3 C -0.6102(10) 0.72281(15) 0.9613(5) 0.0272(14) Uani 1 1 d . . . H3A H -0.4427 0.7238 0.9499 0.033 Uiso 1 1 calc R . . C5 C -0.6085(12) 0.80319(17) 0.9821(6) 0.0326(15) Uani 1 1 d . . . C6 C -0.8314(9) 0.81772(16) 1.0417(6) 0.0327(15) Uani 1 1 d . . . H6A H -0.9189 0.8402 0.9909 0.039 Uiso 1 1 calc R . . H6B H -0.8043 0.8237 1.1388 0.039 Uiso 1 1 calc R . . C7 C -0.9292(10) 0.77269(15) 1.0047(6) 0.0310(15) Uani 1 1 d . . . H7A H -1.0774 0.7726 0.9411 0.037 Uiso 1 1 calc R . . C8 C -0.6174(11) 0.66511(16) 1.1462(5) 0.0291(15) Uani 1 1 d . . . C9 C -0.8048(10) 0.63695(17) 1.1167(6) 0.0351(16) Uani 1 1 d . . . H9A H -0.9517 0.6466 1.0757 0.042 Uiso 1 1 calc R . . C10 C -0.7731(12) 0.59500(18) 1.1481(6) 0.0407(17) Uani 1 1 d . . . H10A H -0.9003 0.5767 1.1285 0.049 Uiso 1 1 calc R . . C11 C -0.5584(12) 0.57950(18) 1.2075(6) 0.0388(17) Uani 1 1 d . . . H11A H -0.5396 0.5510 1.2263 0.047 Uiso 1 1 calc R . . C12 C -0.3692(11) 0.60702(18) 1.2393(6) 0.0368(16) Uani 1 1 d . . . H12A H -0.2238 0.5972 1.2818 0.044 Uiso 1 1 calc R . . C13 C -0.3993(11) 0.64948(17) 1.2070(5) 0.0320(15) Uani 1 1 d . . . H13A H -0.2717 0.6677 1.2262 0.038 Uiso 1 1 calc R . . C14 C -0.7431(13) 0.69294(18) 0.8580(6) 0.0344(16) Uani 1 1 d . . . C15 C -0.7184(11) 0.62693(17) 0.7503(6) 0.0414(17) Uani 1 1 d . . . H15A H -0.7770 0.6373 0.6597 0.050 Uiso 1 1 calc R . . H15B H -0.8508 0.6160 0.7908 0.050 Uiso 1 1 calc R . . C16 C -0.5365(11) 0.59312(17) 0.7429(6) 0.0344(16) Uani 1 1 d . . . C17 C -0.3915(13) 0.58004(18) 0.8545(7) 0.0513(19) Uani 1 1 d . . . H17A H -0.4068 0.5924 0.9380 0.062 Uiso 1 1 calc R . . C18 C -0.2179(13) 0.54871(19) 0.8514(7) 0.055(2) Uani 1 1 d . . . H18A H -0.1180 0.5399 0.9288 0.066 Uiso 1 1 calc R . . C19 C -0.2092(12) 0.53177(18) 0.7199(8) 0.048(2) Uani 1 1 d . . . C20 C -0.3509(14) 0.54370(19) 0.6072(7) 0.055(2) Uani 1 1 d . . . H20A H -0.3383 0.5312 0.5237 0.067 Uiso 1 1 calc R . . C21 C -0.5184(12) 0.57524(17) 0.6161(6) 0.0471(19) Uani 1 1 d . . . H21A H -0.6168 0.5842 0.5384 0.056 Uiso 1 1 calc R . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 S1 0.0370(10) 0.0352(8) 0.0437(10) 0.0004(8) 0.0247(8) 0.0014(8) N2 0.080(6) 0.038(4) 0.126(8) 0.023(5) 0.066(6) 0.016(5) N4 0.030(3) 0.027(3) 0.035(3) 0.005(2) 0.020(2) 0.005(2) O1 0.032(3) 0.042(2) 0.053(3) 0.000(2) 0.018(2) -0.007(2) O2 0.044(3) 0.055(3) 0.051(3) -0.014(2) -0.001(3) 0.014(3) O3 0.040(3) 0.029(2) 0.040(2) -0.005(2) 0.014(2) 0.001(2) O4 0.143(6) 0.055(3) 0.099(5) 0.016(3) 0.086(5) 0.038(3) O5 0.069(5) 0.055(4) 0.181(8) 0.002(5) 0.020(5) 0.018(4) C2 0.015(3) 0.029(3) 0.031(3) -0.010(3) 0.010(3) -0.006(3) C3 0.024(3) 0.036(3) 0.024(3) 0.000(3) 0.012(3) 0.000(3) C5 0.041(4) 0.035(4) 0.024(3) 0.004(3) 0.010(3) 0.001(3) C6 0.030(4) 0.038(3) 0.033(4) -0.003(3) 0.016(3) 0.011(3) C7 0.028(4) 0.035(3) 0.033(3) 0.001(3) 0.015(3) 0.005(3) C8 0.039(4) 0.037(3) 0.015(3) -0.001(3) 0.014(3) 0.003(3) C9 0.030(4) 0.039(4) 0.039(4) -0.002(3) 0.015(3) -0.001(3) C10 0.040(4) 0.034(4) 0.052(4) -0.002(3) 0.022(4) -0.001(3) C11 0.048(5) 0.031(3) 0.041(4) 0.004(3) 0.018(4) 0.007(3) C12 0.035(4) 0.041(4) 0.036(4) -0.002(3) 0.015(3) 0.005(3) C13 0.036(4) 0.037(3) 0.026(3) 0.000(3) 0.014(3) 0.003(3) C14 0.042(5) 0.042(4) 0.022(4) -0.002(3) 0.012(3) 0.007(4) C15 0.053(5) 0.034(3) 0.038(4) -0.008(3) 0.010(4) -0.003(3) C16 0.052(5) 0.025(3) 0.028(4) 0.000(3) 0.015(3) -0.001(3) C17 0.071(5) 0.040(4) 0.043(4) -0.005(3) 0.012(4) 0.016(4) C18 0.063(5) 0.043(4) 0.056(5) -0.001(4) 0.002(4) 0.001(4) C19 0.055(5) 0.025(3) 0.071(5) 0.003(4) 0.036(4) -0.007(3) C20 0.093(6) 0.038(4) 0.041(4) 0.008(3) 0.029(5) 0.009(4) C21 0.072(5) 0.034(4) 0.037(4) 0.005(3) 0.017(4) 0.016(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 S1 C7 1.825(5) . ? S1 C2 1.845(5) . ? N2 O5 1.201(9) . ? N2 O4 1.248(9) . ? N2 C19 1.510(9) . ? N4 C5 1.412(7) . ? N4 C3 1.471(6) . ? N4 C7 1.481(6) . ? O1 C5 1.191(6) . ? O2 C14 1.185(7) . ? O3 C14 1.353(6) . ? O3 C15 1.449(6) . ? C2 C8 1.513(7) . ? C2 C3 1.565(7) . ? C3 C14 1.517(8) . ? C5 C6 1.549(7) . ? C6 C7 1.562(7) . ? C8 C9 1.394(7) . ? C8 C13 1.395(8) . ? C9 C10 1.376(7) . ? C10 C11 1.374(8) . ? C11 C12 1.391(8) . ? C12 C13 1.393(7) . ? C15 C16 1.505(8) . ? C16 C17 1.348(8) . ? C16 C21 1.395(7) . ? C17 C18 1.409(8) . ? C18 C19 1.416(9) . ? C19 C20 1.336(10) . ? C20 C21 1.398(8) . ? 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 C7 S1 C2 94.1(2) . . ? O5 N2 O4 125.0(8) . . ? O5 N2 C19 120.1(9) . . ? O4 N2 C19 114.9(9) . . ? C5 N4 C3 125.7(5) . . ? C5 N4 C7 93.8(4) . . ? C3 N4 C7 115.7(4) . . ? C14 O3 C15 115.4(5) . . ? C8 C2 C3 115.1(4) . . ? C8 C2 S1 112.3(4) . . ? C3 C2 S1 105.5(4) . . ? N4 C3 C14 107.9(5) . . ? N4 C3 C2 105.3(4) . . ? C14 C3 C2 113.1(4) . . ? O1 C5 N4 131.5(5) . . ? O1 C5 C6 137.0(5) . . ? N4 C5 C6 91.5(5) . . ? C5 C6 C7 85.6(4) . . ? N4 C7 C6 88.4(4) . . ? N4 C7 S1 106.4(4) . . ? C6 C7 S1 118.4(4) . . ? C9 C8 C13 118.2(5) . . ? C9 C8 C2 123.5(6) . . ? C13 C8 C2 118.3(5) . . ? C10 C9 C8 120.3(6) . . ? C11 C10 C9 121.7(6) . . ? C10 C11 C12 119.2(5) . . ? C11 C12 C13 119.5(6) . . ? C12 C13 C8 121.2(6) . . ? O2 C14 O3 124.3(6) . . ? O2 C14 C3 125.3(5) . . ? O3 C14 C3 110.2(6) . . ? O3 C15 C16 106.9(5) . . ? C17 C16 C21 119.7(6) . . ? C17 C16 C15 121.9(5) . . ? C21 C16 C15 118.4(6) . . ? C16 C17 C18 123.5(6) . . ? C17 C18 C19 114.0(7) . . ? C20 C19 C18 124.2(6) . . ? C20 C19 N2 121.7(7) . . ? C18 C19 N2 114.1(8) . . ? C19 C20 C21 119.3(6) . . ? C16 C21 C20 119.3(7) . . ? _diffrn_measured_fraction_theta_max 0.999 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 0.999 _refine_diff_density_max 0.360 _refine_diff_density_min -0.363 _refine_diff_density_rms 0.075