# Supplementary Material (ESI) for New Journal of Chemistry # This journal is © The Royal Society of Chemistry and # The Centre National de la Recherche Scientifique, 2000 # CCDC Number: 440/170 data_amsal _audit_creation_method SHELXL _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_formula_moiety ? _chemical_formula_structural ? _chemical_formula_analytical ? _chemical_formula_sum 'C15 H14 N2 O3' _chemical_formula_weight 270.28 _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 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 6.6655(2) _cell_length_b 16.4067(5) _cell_length_c 12.79380(10) _cell_angle_alpha 90.00 _cell_angle_beta 94.307(2) _cell_angle_gamma 90.00 _cell_volume 1395.16(6) _cell_formula_units_Z 4 _cell_measurement_temperature 298(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 0.20 _exptl_crystal_size_mid 0.15 _exptl_crystal_size_min 0.05 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.287 _exptl_crystal_density_method ? _exptl_crystal_F_000 568 _exptl_absorpt_coefficient_mu 0.091 _exptl_absorpt_correction_type Sadabs _exptl_absorpt_correction_T_min 0.346661 _exptl_absorpt_correction_T_max 1.000000 _exptl_special_details ; ? ; _diffrn_ambient_temperature 298(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 'Siemens CCD' _diffrn_measurement_method '\w scans' _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% -2.07 _diffrn_reflns_number 4969 _diffrn_reflns_av_R_equivalents 0.0524 _diffrn_reflns_av_sigmaI/netI 0.0830 _diffrn_reflns_limit_h_min -4 _diffrn_reflns_limit_h_max 7 _diffrn_reflns_limit_k_min -19 _diffrn_reflns_limit_k_max 17 _diffrn_reflns_limit_l_min -12 _diffrn_reflns_limit_l_max 15 _diffrn_reflns_theta_min 2.02 _diffrn_reflns_theta_max 25.04 _reflns_number_total 2451 _reflns_number_observed 1273 _reflns_observed_criterion >2sigma(I) _computing_data_collection 'Siemens SMART' _computing_cell_refinement 'Siemens SMART' _computing_data_reduction 'Siemens SAINT' _computing_structure_solution 'SHELXS-86 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-93 (Sheldrick, 1993)' _computing_molecular_graphics 'Siemens SHELXTL' _computing_publication_material 'Siemens SHELXTL' _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^)+(0.0690P)^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 ? _refine_ls_extinction_method SHELXL _refine_ls_extinction_coef 0.0114(31) _refine_ls_extinction_expression 'Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^' _refine_ls_number_reflns 2451 _refine_ls_number_parameters 182 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.1253 _refine_ls_R_factor_obs 0.0584 _refine_ls_wR_factor_all 0.1590 _refine_ls_wR_factor_obs 0.1288 _refine_ls_goodness_of_fit_all 0.959 _refine_ls_goodness_of_fit_obs 1.114 _refine_ls_restrained_S_all 0.959 _refine_ls_restrained_S_obs 1.114 _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 O1 O 0.1381(3) 0.73322(12) 0.8635(2) 0.0656(6) Uani 1 d . . H1A H 0.2014(3) 0.73912(12) 0.8115(2) 0.098 Uiso 1 calc R . O2 O -0.1474(3) 0.74934(13) 1.1976(2) 0.0732(7) Uani 1 d . . O3 O -0.1175(3) 0.4924(2) 0.8967(3) 0.1204(12) Uani 1 d . . H3A H -0.1378(3) 0.5245(2) 0.9439(3) 0.181 Uiso 1 calc R . N1 N -0.0329(3) 0.72188(13) 1.0396(2) 0.0519(6) Uani 1 d . . H1B H -0.0586(3) 0.69383(13) 0.9834(2) 0.062 Uiso 1 calc R . N2 N -0.3096(3) 0.60272(13) 0.9978(2) 0.0575(7) Uani 1 d . . C1 C 0.2305(4) 0.7756(2) 0.9455(2) 0.0504(7) Uani 1 d . . C2 C 0.4043(4) 0.8211(2) 0.9395(3) 0.0707(10) Uani 1 d . . H2A H 0.4653(4) 0.8239(2) 0.8765(3) 0.085 Uiso 1 calc R . C3 C 0.4874(5) 0.8621(2) 1.0262(3) 0.0823(11) Uani 1 d . . H3B H 0.6044(5) 0.8923(2) 1.0215(3) 0.099 Uiso 1 calc R . C4 C 0.3987(4) 0.8586(2) 1.1192(3) 0.0807(11) Uani 1 d . . H4A H 0.4547(4) 0.8871(2) 1.1771(3) 0.097 Uiso 1 calc R . C5 C 0.2259(4) 0.8129(2) 1.1273(3) 0.0689(9) Uani 1 d . . H5A H 0.1674(4) 0.8099(2) 1.1910(3) 0.083 Uiso 1 calc R . C6 C 0.1403(4) 0.7717(2) 1.0402(2) 0.0478(7) Uani 1 d . . C7 C -0.1631(4) 0.7119(2) 1.1137(2) 0.0509(8) Uani 1 d . . C8 C -0.3311(4) 0.6521(2) 1.0904(3) 0.0638(9) Uani 1 d . . H8A H -0.3388(4) 0.6163(2) 1.1503(3) 0.077 Uiso 1 calc R . H8B H -0.4570(4) 0.6819(2) 1.0813(3) 0.077 Uiso 1 calc R . C9 C -0.4564(4) 0.5929(2) 0.9300(3) 0.0605(9) Uani 1 d . . H9A H -0.5761(4) 0.6201(2) 0.9393(3) 0.073 Uiso 1 calc R . C10 C -0.4460(4) 0.5411(2) 0.8387(3) 0.0582(8) Uani 1 d . . C11 C -0.6051(6) 0.5371(2) 0.7615(4) 0.0920(13) Uani 1 d . . H11A H -0.7188(6) 0.5688(2) 0.7691(4) 0.110 Uiso 1 calc R . C12 C -0.5998(8) 0.4884(3) 0.6751(4) 0.109(2) Uani 1 d . . H12A H -0.7081(8) 0.4872(3) 0.6249(4) 0.131 Uiso 1 calc R . C13 C -0.4339(8) 0.4418(3) 0.6635(4) 0.109(2) Uani 1 d . . H13A H -0.4284(8) 0.4092(3) 0.6043(4) 0.131 Uiso 1 calc R . C14 C -0.2750(6) 0.4424(3) 0.7380(4) 0.108(2) Uani 1 d . . H14A H -0.1647(6) 0.4088(3) 0.7302(4) 0.130 Uiso 1 calc R . C15 C -0.2777(5) 0.4925(2) 0.8249(3) 0.0745(10) 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 O1 0.0708(13) 0.091(2) 0.0367(13) 0.0002(11) 0.0176(10) -0.0132(11) O2 0.0782(14) 0.100(2) 0.045(2) -0.0165(13) 0.0240(12) -0.0098(12) O3 0.0666(14) 0.148(2) 0.143(3) -0.080(2) -0.019(2) 0.035(2) N1 0.0562(13) 0.064(2) 0.0372(14) -0.0091(12) 0.0130(11) -0.0067(11) N2 0.0562(14) 0.058(2) 0.060(2) -0.0060(13) 0.0128(14) -0.0017(12) C1 0.055(2) 0.055(2) 0.042(2) 0.002(2) 0.0078(14) 0.0015(14) C2 0.067(2) 0.084(2) 0.063(3) 0.005(2) 0.021(2) -0.013(2) C3 0.064(2) 0.091(3) 0.092(3) -0.006(2) 0.013(2) -0.022(2) C4 0.062(2) 0.093(3) 0.088(3) -0.030(2) 0.006(2) -0.013(2) C5 0.059(2) 0.095(2) 0.054(2) -0.020(2) 0.009(2) -0.003(2) C6 0.0440(14) 0.060(2) 0.041(2) -0.0016(15) 0.0093(13) 0.0014(13) C7 0.055(2) 0.058(2) 0.041(2) 0.0007(15) 0.0151(14) -0.0004(14) C8 0.071(2) 0.064(2) 0.059(2) 0.000(2) 0.025(2) -0.003(2) C9 0.054(2) 0.048(2) 0.079(3) 0.003(2) 0.005(2) 0.0036(14) C10 0.064(2) 0.051(2) 0.059(2) 0.006(2) 0.003(2) -0.0060(15) C11 0.102(3) 0.066(2) 0.102(4) 0.007(2) -0.035(3) -0.001(2) C12 0.158(4) 0.081(3) 0.081(4) 0.004(3) -0.042(3) -0.025(3) C13 0.158(4) 0.104(3) 0.066(3) -0.024(3) 0.022(3) -0.055(3) C14 0.095(3) 0.126(4) 0.107(4) -0.059(3) 0.034(3) -0.020(3) C15 0.065(2) 0.087(2) 0.072(3) -0.022(2) 0.013(2) -0.005(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 O1 C1 1.367(3) . ? O2 C7 1.235(3) . ? O3 C15 1.355(4) . ? N1 C7 1.342(3) . ? N1 C6 1.414(3) . ? N2 C9 1.268(4) . ? N2 C8 1.451(4) . ? C1 C2 1.385(4) . ? C1 C6 1.394(4) . ? C2 C3 1.377(5) . ? C3 C4 1.369(5) . ? C4 C5 1.384(4) . ? C5 C6 1.389(4) . ? C7 C8 1.501(4) . ? C9 C10 1.450(4) . ? C10 C11 1.395(5) . ? C10 C15 1.399(4) . ? C11 C12 1.366(6) . ? C12 C13 1.361(5) . ? C13 C14 1.371(6) . ? C14 C15 1.383(5) . ? 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 N1 C6 129.6(2) . . ? C9 N2 C8 120.7(3) . . ? O1 C1 C2 124.2(3) . . ? O1 C1 C6 116.4(2) . . ? C2 C1 C6 119.4(3) . . ? C3 C2 C1 120.4(3) . . ? C4 C3 C2 120.4(3) . . ? C3 C4 C5 120.3(3) . . ? C4 C5 C6 119.8(3) . . ? C5 C6 C1 119.8(3) . . ? C5 C6 N1 124.9(2) . . ? C1 C6 N1 115.3(2) . . ? O2 C7 N1 122.4(3) . . ? O2 C7 C8 120.7(2) . . ? N1 C7 C8 116.9(3) . . ? N2 C8 C7 114.1(2) . . ? N2 C9 C10 123.0(3) . . ? C11 C10 C15 117.2(3) . . ? C11 C10 C9 121.2(3) . . ? C15 C10 C9 121.5(3) . . ? C12 C11 C10 122.4(4) . . ? C13 C12 C11 119.2(4) . . ? C12 C13 C14 120.8(4) . . ? C13 C14 C15 120.4(4) . . ? O3 C15 C14 119.1(3) . . ? O3 C15 C10 120.9(3) . . ? C14 C15 C10 119.9(4) . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag O1 C1 C2 C3 179.9(3) . . . . ? C6 C1 C2 C3 0.0(5) . . . . ? C1 C2 C3 C4 -0.3(5) . . . . ? C2 C3 C4 C5 0.9(6) . . . . ? C3 C4 C5 C6 -1.2(5) . . . . ? C4 C5 C6 C1 0.9(5) . . . . ? C4 C5 C6 N1 178.6(3) . . . . ? O1 C1 C6 C5 179.7(3) . . . . ? C2 C1 C6 C5 -0.3(4) . . . . ? O1 C1 C6 N1 1.9(4) . . . . ? C2 C1 C6 N1 -178.2(2) . . . . ? C7 N1 C6 C5 9.5(5) . . . . ? C7 N1 C6 C1 -172.7(3) . . . . ? C6 N1 C7 O2 1.4(5) . . . . ? C6 N1 C7 C8 -178.4(2) . . . . ? C9 N2 C8 C7 -133.1(3) . . . . ? O2 C7 C8 N2 -169.6(3) . . . . ? N1 C7 C8 N2 10.1(4) . . . . ? C8 N2 C9 C10 -177.0(3) . . . . ? N2 C9 C10 C11 -174.7(3) . . . . ? N2 C9 C10 C15 6.1(5) . . . . ? C15 C10 C11 C12 -0.2(5) . . . . ? C9 C10 C11 C12 -179.5(3) . . . . ? C10 C11 C12 C13 0.1(6) . . . . ? C11 C12 C13 C14 1.1(7) . . . . ? C12 C13 C14 C15 -2.2(7) . . . . ? C13 C14 C15 O3 -179.3(4) . . . . ? C13 C14 C15 C10 2.1(6) . . . . ? C11 C10 C15 O3 -179.5(3) . . . . ? C9 C10 C15 O3 -0.2(5) . . . . ? C11 C10 C15 C14 -0.9(5) . . . . ? C9 C10 C15 C14 178.4(3) . . . . ? _refine_diff_density_max 0.171 _refine_diff_density_min -0.177 _refine_diff_density_rms 0.044