# Supplementary Material (ESI) for Perkin Transactions # This journal is © The Royal Society of Chemistry 2000 # CCDC Number: 188/218 data_p21c _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C14 H10 N2 O4' _chemical_formula_weight 270.24 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)/c loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y-1/2, z-1/2' _cell_length_a 9.637(2) _cell_length_b 15.251(3) _cell_length_c 9.109(2) _cell_angle_alpha 90.00 _cell_angle_beta 96.86(3) _cell_angle_gamma 90.00 _cell_volume 1329.1(5) _cell_formula_units_Z 4 _cell_measurement_temperature 294(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description plate _exptl_crystal_colour yellow _exptl_crystal_size_max 0.60 _exptl_crystal_size_mid 0.40 _exptl_crystal_size_min 0.18 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.350 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 560 _exptl_absorpt_coefficient_mu 0.101 _exptl_absorpt_correction_type 'abscor' _exptl_absorpt_correction_T_min 0.655 _exptl_absorpt_correction_T_max 1.224 _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 294(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'rotation anode' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'IP Rigaku' _diffrn_measurement_method 'IP' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 3385 _diffrn_reflns_av_R_equivalents 0.0475 _diffrn_reflns_av_sigmaI/netI 0.0630 _diffrn_reflns_limit_h_min -11 _diffrn_reflns_limit_h_max 11 _diffrn_reflns_limit_k_min -18 _diffrn_reflns_limit_k_max 18 _diffrn_reflns_limit_l_min 0 _diffrn_reflns_limit_l_max 10 _diffrn_reflns_theta_min 2.13 _diffrn_reflns_theta_max 25.55 _reflns_number_total 2041 _reflns_number_gt 1678 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'RAXIS Rigaku' _computing_cell_refinement 'BIOTEX Rigaku' _computing_data_reduction 'BIOTEX Rigaku' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Siemens SHELXTL' _computing_publication_material 'Siemens 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^)+(0.0720P)^2^+0.1368P] 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 SHELXL _refine_ls_extinction_coef 0.037(2) _refine_ls_extinction_expression 'Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^' _refine_ls_number_reflns 2041 _refine_ls_number_parameters 182 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0784 _refine_ls_R_factor_gt 0.0587 _refine_ls_wR_factor_ref 0.1571 _refine_ls_wR_factor_gt 0.1440 _refine_ls_goodness_of_fit_ref 1.109 _refine_ls_restrained_S_all 1.109 _refine_ls_shift/su_max 0.080 _refine_ls_shift/su_mean 0.005 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 O1 O 0.07350(10) 0.66308(6) 0.11343(11) 0.0853(3) Uani 1 1 d . . . O2 O 0.16457(17) 0.60055(7) 0.31455(15) 0.1322(5) Uani 1 1 d . . . O3 O 0.42540(12) 0.68739(9) 0.32018(12) 0.1199(4) Uani 1 1 d . . . O4 O 0.36622(11) 0.76513(7) 0.49764(11) 0.0896(3) Uani 1 1 d . . . C1 C 0.14520(11) 0.82696(7) 0.26766(11) 0.0521(3) Uani 1 1 d . . . C2 C 0.20503(12) 0.74715(7) 0.29032(13) 0.0561(3) Uani 1 1 d . . . C3 C -0.00459(11) 0.83575(7) 0.20771(12) 0.0545(3) Uani 1 1 d . . . C4 C -0.04375(13) 0.89162(8) 0.08935(14) 0.0666(4) Uani 1 1 d . . . H4A H 0.0239 0.9238 0.0483 0.080 Uiso 1 1 calc R . . C5 C -0.18313(15) 0.89955(9) 0.03225(17) 0.0833(5) Uani 1 1 d . . . H5A H -0.2083 0.9361 -0.0483 0.100 Uiso 1 1 calc R . . C6 C -0.28341(15) 0.85400(10) 0.09379(17) 0.0867(5) Uani 1 1 d . . . H6A H -0.3766 0.8591 0.0545 0.104 Uiso 1 1 calc R . . C7 C -0.24703(14) 0.80042(10) 0.21407(18) 0.0851(5) Uani 1 1 d . . . H7A H -0.3161 0.7708 0.2573 0.102 Uiso 1 1 calc R . . C8 C -0.10760(13) 0.79039(8) 0.27102(15) 0.0690(4) Uani 1 1 d . . . H8A H -0.0833 0.7535 0.3512 0.083 Uiso 1 1 calc R . . C9 C 0.22754(11) 0.90837(7) 0.30112(12) 0.0539(3) Uani 1 1 d . . . C10 C 0.16973(13) 0.97838(8) 0.37057(14) 0.0643(4) Uani 1 1 d . . . H10A H 0.0790 0.9743 0.3952 0.077 Uiso 1 1 calc R . . C11 C 0.24678(15) 1.05438(8) 0.40343(16) 0.0759(4) Uani 1 1 d . . . H11A H 0.2088 1.1000 0.4533 0.091 Uiso 1 1 calc R . . C12 C 0.37885(14) 1.06229(9) 0.36254(16) 0.0782(4) Uani 1 1 d . . . H12A H 0.4300 1.1133 0.3848 0.094 Uiso 1 1 calc R . . C13 C 0.43607(14) 0.99477(9) 0.28840(16) 0.0766(4) Uani 1 1 d . . . H13A H 0.5246 1.0008 0.2587 0.092 Uiso 1 1 calc R . . C14 C 0.36092(12) 0.91802(8) 0.25842(15) 0.0652(4) Uani 1 1 d . . . H14A H 0.3999 0.8724 0.2093 0.078 Uiso 1 1 calc R . . N1 N 0.14226(12) 0.66378(7) 0.23500(13) 0.0727(3) Uani 1 1 d . . . N2 N 0.34195(11) 0.73214(7) 0.37595(12) 0.0686(3) Uani 1 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 0.0744(6) 0.0819(6) 0.0980(6) -0.0232(5) 0.0038(5) -0.0049(5) O2 0.2036(13) 0.0612(6) 0.1311(9) 0.0255(6) 0.0170(9) -0.0042(7) O3 0.0986(6) 0.1692(9) 0.0897(7) -0.0085(7) 0.0022(6) 0.0750(6) O4 0.0854(6) 0.1063(7) 0.0719(6) -0.0051(5) -0.0112(5) 0.0166(6) C1 0.0495(6) 0.0565(6) 0.0505(6) 0.0009(5) 0.0064(5) -0.0006(5) C2 0.0498(6) 0.0595(6) 0.0586(7) 0.0011(5) 0.0044(5) 0.0034(5) C3 0.0490(6) 0.0542(6) 0.0601(6) -0.0032(5) 0.0056(5) 0.0010(5) C4 0.0603(7) 0.0669(7) 0.0702(7) 0.0055(6) -0.0028(6) -0.0011(6) C5 0.0767(8) 0.0822(9) 0.0838(9) 0.0000(8) -0.0197(7) 0.0137(7) C6 0.0545(7) 0.0966(9) 0.1041(10) -0.0215(9) -0.0106(7) 0.0053(7) C7 0.0532(7) 0.0922(9) 0.1115(11) -0.0155(9) 0.0163(7) -0.0116(7) C8 0.0566(7) 0.0689(7) 0.0820(8) 0.0004(7) 0.0109(6) -0.0031(6) C9 0.0466(6) 0.0574(6) 0.0562(6) 0.0039(5) 0.0006(5) 0.0003(5) C10 0.0611(7) 0.0615(7) 0.0704(7) -0.0023(6) 0.0083(6) 0.0000(6) C11 0.0861(9) 0.0610(7) 0.0793(8) -0.0095(7) 0.0050(7) -0.0012(7) C12 0.0739(8) 0.0695(7) 0.0868(9) 0.0026(7) -0.0090(7) -0.0177(7) C13 0.0545(7) 0.0783(8) 0.0955(9) 0.0092(8) 0.0030(7) -0.0082(7) C14 0.0536(7) 0.0650(7) 0.0768(8) 0.0004(7) 0.0074(6) -0.0001(6) N1 0.0791(7) 0.0558(6) 0.0857(7) 0.0003(6) 0.0203(6) 0.0023(5) N2 0.0659(6) 0.0769(6) 0.0629(6) 0.0073(5) 0.0070(5) 0.0191(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 O1 N1 1.2208(15) . ? O2 N1 1.2100(15) . ? O3 N2 1.2116(16) . ? O4 N2 1.2144(14) . ? C1 C2 1.3520(15) . ? C1 C9 1.4854(15) . ? C1 C3 1.4872(15) . ? C2 N2 1.4683(16) . ? C2 N1 1.4710(15) . ? C3 C8 1.3904(17) . ? C3 C4 1.3905(16) . ? C4 C5 1.3864(19) . ? C5 C6 1.364(2) . ? C6 C7 1.378(2) . ? C7 C8 1.3897(19) . ? C9 C10 1.3909(17) . ? C9 C14 1.3945(17) . ? C10 C11 1.3898(18) . ? C11 C12 1.373(2) . ? C12 C13 1.382(2) . ? C13 C14 1.3862(18) . ? 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 C2 C1 C9 120.90(10) . . ? C2 C1 C3 120.98(10) . . ? C9 C1 C3 118.11(9) . . ? C1 C2 N2 124.14(10) . . ? C1 C2 N1 125.13(10) . . ? N2 C2 N1 110.72(9) . . ? C8 C3 C4 119.03(11) . . ? C8 C3 C1 120.84(10) . . ? C4 C3 C1 120.11(10) . . ? C5 C4 C3 120.36(12) . . ? C6 C5 C4 120.24(13) . . ? C5 C6 C7 120.22(13) . . ? C6 C7 C8 120.32(14) . . ? C7 C8 C3 119.79(12) . . ? C10 C9 C14 118.58(11) . . ? C10 C9 C1 120.13(10) . . ? C14 C9 C1 121.23(10) . . ? C11 C10 C9 120.36(12) . . ? C12 C11 C10 120.23(13) . . ? C11 C12 C13 120.26(13) . . ? C12 C13 C14 119.73(13) . . ? C13 C14 C9 120.76(12) . . ? O2 N1 O1 125.08(11) . . ? O2 N1 C2 116.58(11) . . ? O1 N1 C2 118.34(10) . . ? O3 N2 O4 123.43(11) . . ? O3 N2 C2 117.67(11) . . ? O4 N2 C2 118.90(11) . . ? _diffrn_measured_fraction_theta_max 0.822 _diffrn_reflns_theta_full 25.55 _diffrn_measured_fraction_theta_full 0.822 _refine_diff_density_max 0.181 _refine_diff_density_min -0.207 _refine_diff_density_rms 0.044