# Supplementary Material (ESI) for Perkin Transactions # This journal is © The Royal Society of Chemistry 2000 # CCDC Number: 188/248 data_shirley2 _audit_creation_method SHELXL _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_formula_moiety 'C13 H16 N O3' _chemical_formula_structural 'C13 H16 N O3' _chemical_formula_analytical ? _chemical_formula_sum 'C13 H16 N O3' _chemical_formula_weight 234.27 _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 Orthorhombic _symmetry_space_group_name_H-M 'P 21 21 21 (no. 19)' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, -y, z+1/2' 'x+1/2, -y+1/2, -z' '-x, y+1/2, -z+1/2' _cell_length_a 7.9732(7) _cell_length_b 10.1799(12) _cell_length_c 15.570(2) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 1263.8(2) _cell_formula_units_Z 4 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 25 _cell_measurement_theta_min 10 _cell_measurement_theta_max 11 _exptl_crystal_description 'irregular blocks' _exptl_crystal_colour 'pale yellow' _exptl_crystal_size_max 0.24 _exptl_crystal_size_mid 0.30 _exptl_crystal_size_min 0.70 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.231 _exptl_crystal_density_method ? _exptl_crystal_F_000 500 _exptl_absorpt_coefficient_mu 0.088 _exptl_absorpt_correction_type 'not applied' _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 293(2) _diffrn_radiation_wavelength 0.71069 _diffrn_radiation_type Mo-K\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device 'Enraf-Nonius CAD4 diffractometer' _diffrn_measurement_method 'scintillation counter; \w/\q scans' _diffrn_standards_number 3 _diffrn_standards_interval_count ? _diffrn_standards_interval_time '10000 s' _diffrn_standards_decay_% 0 _diffrn_reflns_number 1780 _diffrn_reflns_av_R_equivalents 0.028 _diffrn_reflns_av_sigmaI/netI 0.0404 _diffrn_reflns_limit_h_min -1 _diffrn_reflns_limit_h_max 9 _diffrn_reflns_limit_k_min -1 _diffrn_reflns_limit_k_max 12 _diffrn_reflns_limit_l_min -1 _diffrn_reflns_limit_l_max 18 _diffrn_reflns_theta_min 2. _diffrn_reflns_theta_max 25. _reflns_number_total 1297 _reflns_number_observed 1147 _reflns_observed_criterion >2sigma(I) _computing_data_collection 'CAD4/EXPRESS (Enraf-Nonius, 1992)' _computing_cell_refinement 'CAD4/EXPRESS (Enraf-Nonius, 1992)' _computing_data_reduction 'CAD4 (Hursthouse, 1976)' _computing_structure_solution 'SHELXS-86 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-93 (Sheldrick, 1993)' _computing_molecular_graphics 'ORTEP (Johnson, 1971)' _computing_publication_material 'SHELXL-93 (Sheldrick, 1993)' _refine_special_details ; Refinement on F^2^ for ALL reflections. Weighted R-factors wR and all goodnesses of fit S are based on F^2^, conventional R- factors R are based on F. 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^)+(0.0392P)^2^+0.1209P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens difmap _refine_ls_hydrogen_treatment free _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 -3.40(183) _refine_ls_number_reflns 1297 _refine_ls_number_parameters 218 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0370 _refine_ls_R_factor_obs 0.0326 _refine_ls_wR_factor_all 0.0828 _refine_ls_wR_factor_obs 0.0791 _refine_ls_goodness_of_fit_all 1.066 _refine_ls_goodness_of_fit_obs 1.096 _refine_ls_restrained_S_all 1.066 _refine_ls_restrained_S_obs 1.096 _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 0.1268(3) 0.1863(2) 0.39413(14) 0.0418(5) Uani 1 d . . C2 C -0.0017(3) 0.2450(2) 0.4408(2) 0.0544(6) Uani 1 d . . H2 H -0.0780(33) 0.1897(25) 0.4692(16) 0.055(7) Uiso 1 d . . C3 C -0.0146(3) 0.3799(2) 0.4459(2) 0.0578(7) Uani 1 d . . H3 H -0.1077(38) 0.4212(28) 0.4813(18) 0.072(8) Uiso 1 d . . C4 C 0.1026(3) 0.4557(2) 0.40331(15) 0.0409(5) Uani 1 d . . C5 C 0.2295(3) 0.3986(2) 0.35570(13) 0.0378(5) Uani 1 d . . C6 C 0.2435(3) 0.2630(2) 0.35093(15) 0.0394(5) Uani 1 d . . H6 H 0.3230(30) 0.2223(21) 0.3209(15) 0.038(6) Uiso 1 d . . C7 C 0.1096(3) 0.6041(2) 0.40052(14) 0.0405(5) Uani 1 d . . C8 C 0.1400(4) 0.6635(3) 0.4887(2) 0.0558(7) Uani 1 d . . H8A H 0.1502(34) 0.7590(32) 0.4849(18) 0.064(8) Uiso 1 d . . H8B H 0.0378(43) 0.6418(29) 0.5274(20) 0.081(9) Uiso 1 d . . H8C H 0.2366(42) 0.6220(30) 0.5177(20) 0.079(9) Uiso 1 d . . C9 C -0.0434(4) 0.6633(3) 0.3566(2) 0.0564(7) Uani 1 d . . H9A H -0.0584(37) 0.6213(28) 0.3007(19) 0.064(7) Uiso 1 d . . H9B H -0.0288(35) 0.7609(30) 0.3526(18) 0.068(8) Uiso 1 d . . H9C H -0.1406(45) 0.6466(31) 0.3933(20) 0.083(10) Uiso 1 d . . C10 C 0.3408(3) 0.5001(2) 0.31315(14) 0.0404(5) Uani 1 d . . C11 C 0.5216(3) 0.4942(3) 0.3434(2) 0.0550(6) Uani 1 d . . H11A H 0.5751(41) 0.4091(31) 0.3277(19) 0.071(8) Uiso 1 d . . H11B H 0.5811(40) 0.5669(29) 0.3199(19) 0.066(9) Uiso 1 d . . H11C H 0.5290(36) 0.4986(27) 0.4042(18) 0.065(8) Uiso 1 d . . C12 C 0.3301(4) 0.4947(3) 0.2157(2) 0.0566(6) Uani 1 d . . H12A H 0.3758(39) 0.4173(29) 0.1968(18) 0.065(8) Uiso 1 d . . H12B H 0.3889(40) 0.5679(28) 0.1938(18) 0.062(8) Uiso 1 d . . H12C H 0.2113(43) 0.5091(32) 0.1993(20) 0.076(9) Uiso 1 d . . C13 C 0.1316(3) 0.0404(2) 0.39169(14) 0.0435(5) Uani 1 d . . O1 O 0.2549(3) -0.0074(2) 0.34554(15) 0.0713(6) Uani 1 d . . H1 H 0.2549(42) -0.0916(33) 0.3438(19) 0.079(9) Uiso 1 d . . O2 O 0.0330(3) -0.0280(2) 0.42850(14) 0.0740(6) Uani 1 d . . N2 N 0.2594(3) 0.6217(2) 0.34561(13) 0.0465(5) Uani 1 d . . O3 O 0.3163(2) 0.73503(15) 0.32468(14) 0.0652(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 0.0484(12) 0.0335(10) 0.0435(11) -0.0002(9) 0.0037(11) -0.0019(10) C2 0.0553(15) 0.0402(12) 0.068(2) 0.0036(12) 0.0217(14) -0.0050(12) C3 0.0611(15) 0.0404(12) 0.072(2) -0.0022(12) 0.0300(14) 0.0009(12) C4 0.0419(11) 0.0336(10) 0.0470(12) -0.0022(9) 0.0058(10) -0.0005(10) C5 0.0390(11) 0.0328(9) 0.0417(11) -0.0015(9) 0.0024(10) -0.0022(9) C6 0.0398(11) 0.0327(9) 0.0458(11) -0.0047(9) 0.0056(11) 0.0001(10) C7 0.0425(12) 0.0319(10) 0.0471(12) -0.0021(10) 0.0065(10) 0.0017(9) C8 0.073(2) 0.0421(13) 0.0526(14) -0.0042(11) -0.0040(15) 0.0050(13) C9 0.0530(15) 0.0451(14) 0.071(2) -0.0065(13) -0.0092(14) 0.0023(12) C10 0.0408(11) 0.0322(10) 0.0484(11) -0.0010(9) 0.0054(10) -0.0034(10) C11 0.0431(13) 0.0554(15) 0.067(2) 0.0039(15) 0.0035(13) -0.0075(12) C12 0.065(2) 0.0536(15) 0.0513(14) 0.0026(13) 0.0088(13) -0.0075(15) C13 0.0485(12) 0.0341(10) 0.0480(12) 0.0007(10) 0.0018(12) -0.0041(11) O1 0.0791(12) 0.0313(8) 0.103(2) -0.0020(10) 0.0392(13) 0.0008(9) O2 0.0853(13) 0.0380(8) 0.0986(15) 0.0036(9) 0.0357(13) -0.0088(10) N2 0.0503(11) 0.0274(8) 0.0618(11) 0.0010(9) 0.0121(10) -0.0039(9) O3 0.0696(12) 0.0302(7) 0.0956(14) 0.0028(8) 0.0271(11) -0.0077(8) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag C1 C6 1.389(3) . ? C1 C2 1.391(3) . ? C1 C13 1.486(3) . ? C2 C3 1.379(3) . ? C2 H2 0.94(3) . ? C3 C4 1.382(3) . ? C3 H3 1.02(3) . ? C4 C5 1.383(3) . ? C4 C7 1.512(3) . ? C5 C6 1.387(3) . ? C5 C10 1.515(3) . ? C6 H6 0.89(2) . ? C7 N2 1.480(3) . ? C7 C8 1.520(3) . ? C7 C9 1.523(3) . ? C8 H8A 0.98(3) . ? C8 H8B 1.04(3) . ? C8 H8C 0.99(3) . ? C9 H9A 0.98(3) . ? C9 H9B 1.00(3) . ? C9 H9C 0.98(3) . ? C10 N2 1.486(3) . ? C10 C11 1.517(3) . ? C10 C12 1.521(3) . ? C11 H11A 1.00(3) . ? C11 H11B 0.95(3) . ? C11 H11C 0.95(3) . ? C12 H12A 0.92(3) . ? C12 H12B 0.94(3) . ? C12 H12C 0.99(3) . ? C13 O2 1.196(3) . ? C13 O1 1.312(3) . ? O1 H1 0.86(3) . ? N2 O3 1.282(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 C6 C1 C2 120.3(2) . . ? C6 C1 C13 122.2(2) . . ? C2 C1 C13 117.5(2) . . ? C3 C2 C1 120.9(2) . . ? C3 C2 H2 121.4(15) . . ? C1 C2 H2 117.7(15) . . ? C2 C3 C4 118.5(2) . . ? C2 C3 H3 119.9(16) . . ? C4 C3 H3 121.6(16) . . ? C3 C4 C5 121.2(2) . . ? C3 C4 C7 126.6(2) . . ? C5 C4 C7 112.2(2) . . ? C4 C5 C6 120.4(2) . . ? C4 C5 C10 112.1(2) . . ? C6 C5 C10 127.5(2) . . ? C5 C6 C1 118.7(2) . . ? C5 C6 H6 123.3(14) . . ? C1 C6 H6 118.0(14) . . ? N2 C7 C4 99.6(2) . . ? N2 C7 C8 110.2(2) . . ? C4 C7 C8 112.2(2) . . ? N2 C7 C9 109.8(2) . . ? C4 C7 C9 112.2(2) . . ? C8 C7 C9 112.1(2) . . ? C7 C8 H8A 110.7(17) . . ? C7 C8 H8B 108.4(17) . . ? H8A C8 H8B 108.2(24) . . ? C7 C8 H8C 111.6(18) . . ? H8A C8 H8C 112.8(25) . . ? H8B C8 H8C 104.8(23) . . ? C7 C9 H9A 109.0(17) . . ? C7 C9 H9B 109.1(17) . . ? H9A C9 H9B 113.2(24) . . ? C7 C9 H9C 107.6(19) . . ? H9A C9 H9C 110.3(26) . . ? H9B C9 H9C 107.4(25) . . ? N2 C10 C5 99.4(2) . . ? N2 C10 C11 110.0(2) . . ? C5 C10 C11 113.2(2) . . ? N2 C10 C12 110.2(2) . . ? C5 C10 C12 112.2(2) . . ? C11 C10 C12 111.2(2) . . ? C10 C11 H11A 111.4(18) . . ? C10 C11 H11B 108.9(18) . . ? H11A C11 H11B 111.6(23) . . ? C10 C11 H11C 111.5(18) . . ? H11A C11 H11C 105.0(24) . . ? H11B C11 H11C 108.3(26) . . ? C10 C12 H12A 109.2(18) . . ? C10 C12 H12B 107.7(18) . . ? H12A C12 H12B 111.4(25) . . ? C10 C12 H12C 107.8(18) . . ? H12A C12 H12C 115.2(29) . . ? H12B C12 H12C 105.3(27) . . ? O2 C13 O1 122.6(2) . . ? O2 C13 C1 123.6(2) . . ? O1 C13 C1 113.8(2) . . ? C13 O1 H1 112.9(22) . . ? O3 N2 C7 122.8(2) . . ? O3 N2 C10 120.6(2) . . ? C7 N2 C10 116.6(2) . . ? _refine_diff_density_max 0.107 _refine_diff_density_min -0.146 _refine_diff_density_rms 0.033