# Supplementary Material (ESI) for Journal of Materials Chemistry # This journal is © The Royal Society of Chemistry 2000 # CCDC Number: 1145/219 data_y685 _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C12 H10 N2 O3' _chemical_formula_weight 230.22 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 7.2340(10) _cell_length_b 8.9990(10) _cell_length_c 16.907(2) _cell_angle_alpha 90.00 _cell_angle_beta 92.420(10) _cell_angle_gamma 90.00 _cell_volume 1099.6(2) _cell_formula_units_Z 4 _cell_measurement_temperature 296(2) _cell_measurement_reflns_used 25 _cell_measurement_theta_min 2.56 _cell_measurement_theta_max 17.51 _exptl_crystal_description ? _exptl_crystal_colour ? _exptl_crystal_size_max 0.58 _exptl_crystal_size_mid 0.28 _exptl_crystal_size_min 0.28 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.391 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 480 _exptl_absorpt_coefficient_mu 0.102 _exptl_absorpt_correction_type none _exptl_absorpt_correction_T_min 0.9431 _exptl_absorpt_correction_T_max 0.9719 _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 296(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'normal-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type ? _diffrn_measurement_method '\w scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number 3 _diffrn_standards_interval_count 97 _diffrn_standards_interval_time ? _diffrn_standards_decay_% 2.41 _diffrn_reflns_number 2624 _diffrn_reflns_av_R_equivalents 0.0118 _diffrn_reflns_av_sigmaI/netI 0.0272 _diffrn_reflns_limit_h_min 0 _diffrn_reflns_limit_h_max 8 _diffrn_reflns_limit_k_min -1 _diffrn_reflns_limit_k_max 10 _diffrn_reflns_limit_l_min -20 _diffrn_reflns_limit_l_max 20 _diffrn_reflns_theta_min 2.41 _diffrn_reflns_theta_max 25.00 _reflns_number_total 1937 _reflns_number_gt 1182 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Siemens XSCANS' _computing_cell_refinement 'Siemens XSCANS' _computing_data_reduction 'Siemens SHELXTL' _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^)+(0.0454P)^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 none _refine_ls_extinction_method SHELXL _refine_ls_extinction_coef 0.039(3) _refine_ls_extinction_expression 'Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^' _refine_ls_number_reflns 1937 _refine_ls_number_parameters 163 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0577 _refine_ls_R_factor_gt 0.0322 _refine_ls_wR_factor_ref 0.0834 _refine_ls_wR_factor_gt 0.0770 _refine_ls_goodness_of_fit_ref 0.905 _refine_ls_restrained_S_all 0.905 _refine_ls_shift/su_max 0.000 _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 O1 O 0.51588(14) 0.13356(11) 0.22908(6) 0.0740(3) Uani 1 1 d . . . O2 O 0.8751(2) -0.22353(16) -0.03917(8) 0.1122(5) Uani 1 1 d . . . O3 O 0.6103(2) -0.33140(16) -0.04034(8) 0.1106(5) Uani 1 1 d . . . N1 N -0.1522(3) 0.0890(2) 0.37943(14) 0.0904(5) Uani 1 1 d . . . N2 N 0.7191(3) -0.23843(17) -0.01489(8) 0.0810(4) Uani 1 1 d . . . C1 C 0.0164(2) 0.09613(16) 0.34172(9) 0.0609(4) Uani 1 1 d . . . C2 C 0.1612(2) 0.00120(16) 0.36107(9) 0.0653(4) Uani 1 1 d . . . H2 H 0.1475 -0.0704 0.4001 0.078 Uiso 1 1 calc R . . C3 C 0.3265(2) 0.01132(16) 0.32315(9) 0.0638(4) Uani 1 1 d . . . H3 H 0.4236 -0.0528 0.3365 0.077 Uiso 1 1 calc R . . C4 C 0.34560(19) 0.11706(16) 0.26552(8) 0.0560(4) Uani 1 1 d . . . C5 C 0.2052(2) 0.21376(16) 0.24665(8) 0.0620(4) Uani 1 1 d . . . H5 H 0.2199 0.2859 0.2080 0.074 Uiso 1 1 calc R . . C6 C 0.0428(2) 0.20383(17) 0.28489(9) 0.0654(4) Uani 1 1 d . . . H6 H -0.0518 0.2709 0.2724 0.078 Uiso 1 1 calc R . . C7 C 0.5536(2) 0.04146(16) 0.16717(8) 0.0563(4) Uani 1 1 d . . . C8 C 0.7283(2) 0.05586(18) 0.13778(9) 0.0688(4) Uani 1 1 d . . . H8 H 0.8094 0.1274 0.1586 0.083 Uiso 1 1 calc R . . C9 C 0.7819(2) -0.03508(19) 0.07814(8) 0.0705(5) Uani 1 1 d . . . H9 H 0.8995 -0.0265 0.0585 0.085 Uiso 1 1 calc R . . C10 C 0.6599(2) -0.13910(17) 0.04766(8) 0.0604(4) Uani 1 1 d . . . C11 C 0.4854(2) -0.15154(16) 0.07424(8) 0.0628(4) Uani 1 1 d . . . H11 H 0.4036 -0.2208 0.0517 0.075 Uiso 1 1 calc R . . C12 C 0.4304(2) -0.06088(15) 0.13488(8) 0.0593(4) Uani 1 1 d . . . H12 H 0.3118 -0.0688 0.1537 0.071 Uiso 1 1 calc R . . H1A H -0.151(2) 0.007(2) 0.4107(10) 0.096(7) Uiso 1 1 d . . . H1B H -0.249(4) 0.117(3) 0.3537(17) 0.186(15) Uiso 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 0.0712(7) 0.0727(7) 0.0793(7) -0.0231(6) 0.0179(6) -0.0178(6) O2 0.1139(11) 0.1355(12) 0.0895(9) -0.0183(9) 0.0325(8) 0.0199(10) O3 0.1459(13) 0.0993(10) 0.0870(9) -0.0346(8) 0.0073(9) -0.0035(9) N1 0.0845(13) 0.0833(13) 0.1057(13) -0.0120(11) 0.0318(11) -0.0053(10) N2 0.1083(12) 0.0814(11) 0.0535(8) 0.0007(8) 0.0057(8) 0.0164(10) C1 0.0638(10) 0.0540(9) 0.0652(9) -0.0163(8) 0.0077(8) -0.0029(8) C2 0.0822(11) 0.0533(9) 0.0606(9) 0.0044(8) 0.0057(8) -0.0051(9) C3 0.0653(10) 0.0530(9) 0.0725(9) -0.0006(8) -0.0044(8) 0.0058(8) C4 0.0600(9) 0.0532(9) 0.0548(8) -0.0098(7) 0.0031(7) -0.0069(8) C5 0.0796(10) 0.0526(9) 0.0535(9) 0.0012(7) -0.0029(8) -0.0015(9) C6 0.0671(10) 0.0570(9) 0.0713(10) -0.0065(8) -0.0067(8) 0.0083(8) C7 0.0643(9) 0.0528(9) 0.0520(8) 0.0014(7) 0.0043(7) -0.0035(8) C8 0.0645(10) 0.0785(11) 0.0637(9) -0.0046(9) 0.0038(8) -0.0136(9) C9 0.0650(10) 0.0898(12) 0.0575(9) 0.0025(9) 0.0101(8) 0.0008(9) C10 0.0793(11) 0.0587(9) 0.0435(8) 0.0045(7) 0.0048(8) 0.0080(9) C11 0.0834(11) 0.0529(9) 0.0517(8) 0.0040(7) -0.0008(8) -0.0093(8) C12 0.0646(9) 0.0554(9) 0.0580(8) 0.0019(8) 0.0061(7) -0.0087(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 O1 C7 1.3716(16) . ? O1 C4 1.4081(16) . ? O2 N2 1.2242(18) . ? O3 N2 1.2147(17) . ? N1 C1 1.402(2) . ? N2 C10 1.4624(19) . ? C1 C2 1.380(2) . ? C1 C6 1.384(2) . ? C2 C3 1.3832(19) . ? C3 C4 1.3731(19) . ? C4 C5 1.3649(19) . ? C5 C6 1.368(2) . ? C7 C12 1.3783(18) . ? C7 C8 1.3834(19) . ? C8 C9 1.367(2) . ? C9 C10 1.372(2) . ? C10 C11 1.363(2) . ? C11 C12 1.3818(19) . ? 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 O1 C4 118.44(11) . . ? O3 N2 O2 123.30(16) . . ? O3 N2 C10 118.17(17) . . ? O2 N2 C10 118.53(17) . . ? C2 C1 C6 118.20(14) . . ? C2 C1 N1 122.01(18) . . ? C6 C1 N1 119.76(17) . . ? C1 C2 C3 120.76(14) . . ? C4 C3 C2 119.31(14) . . ? C5 C4 C3 120.76(13) . . ? C5 C4 O1 119.11(13) . . ? C3 C4 O1 119.98(14) . . ? C4 C5 C6 119.56(14) . . ? C5 C6 C1 121.37(14) . . ? O1 C7 C12 124.03(13) . . ? O1 C7 C8 115.58(13) . . ? C12 C7 C8 120.38(14) . . ? C9 C8 C7 120.02(15) . . ? C8 C9 C10 119.19(14) . . ? C11 C10 C9 121.49(14) . . ? C11 C10 N2 119.47(16) . . ? C9 C10 N2 119.04(15) . . ? C10 C11 C12 119.74(14) . . ? C7 C12 C11 119.13(14) . . ? 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 C6 C1 C2 C3 -1.6(2) . . . . ? N1 C1 C2 C3 -179.66(15) . . . . ? C1 C2 C3 C4 -0.2(2) . . . . ? C2 C3 C4 C5 1.4(2) . . . . ? C2 C3 C4 O1 176.91(13) . . . . ? C7 O1 C4 C5 -100.90(15) . . . . ? C7 O1 C4 C3 83.53(16) . . . . ? C3 C4 C5 C6 -0.9(2) . . . . ? O1 C4 C5 C6 -176.40(13) . . . . ? C4 C5 C6 C1 -1.0(2) . . . . ? C2 C1 C6 C5 2.2(2) . . . . ? N1 C1 C6 C5 -179.72(15) . . . . ? C4 O1 C7 C12 4.1(2) . . . . ? C4 O1 C7 C8 -175.43(13) . . . . ? O1 C7 C8 C9 177.41(13) . . . . ? C12 C7 C8 C9 -2.2(2) . . . . ? C7 C8 C9 C10 0.6(2) . . . . ? C8 C9 C10 C11 1.5(2) . . . . ? C8 C9 C10 N2 -178.63(12) . . . . ? O3 N2 C10 C11 -1.3(2) . . . . ? O2 N2 C10 C11 178.49(15) . . . . ? O3 N2 C10 C9 178.87(14) . . . . ? O2 N2 C10 C9 -1.4(2) . . . . ? C9 C10 C11 C12 -2.0(2) . . . . ? N2 C10 C11 C12 178.16(12) . . . . ? O1 C7 C12 C11 -177.84(12) . . . . ? C8 C7 C12 C11 1.7(2) . . . . ? C10 C11 C12 C7 0.3(2) . . . . ? _diffrn_measured_fraction_theta_max 0.999 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 0.999 _refine_diff_density_max 0.103 _refine_diff_density_min -0.084 _refine_diff_density_rms 0.024