# Supplementary Material (ESI) for Dalton Transactions # This journal is (c) The Royal Society of Chemistry 2010 data_2 _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C18 H12 N2 O2' _chemical_formula_sum 'C18 H12 N2 O2' _chemical_formula_weight 288.30 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 Iba2 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, z' 'x+1/2, -y+1/2, z' '-x+1/2, y+1/2, z' 'x+1/2, y+1/2, z+1/2' '-x+1/2, -y+1/2, z+1/2' 'x+1, -y+1, z+1/2' '-x+1, y+1, z+1/2' _cell_length_a 14.333(9) _cell_length_b 25.751(16) _cell_length_c 7.859(5) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 2901(3) _cell_formula_units_Z 8 _cell_measurement_temperature 150(2) _cell_measurement_reflns_used 5183 _cell_measurement_theta_min 2.5 _cell_measurement_theta_max 26 _exptl_crystal_description block _exptl_crystal_colour yellow _exptl_crystal_size_max 0.6 _exptl_crystal_size_mid 0.3 _exptl_crystal_size_min 0.3 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.320 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1200 _exptl_absorpt_coefficient_mu 0.088 _exptl_absorpt_correction_type multiscan _exptl_absorpt_correction_T_min 0.632 _exptl_absorpt_correction_T_max 1 _exptl_absorpt_process_details sadabs _exptl_special_details ; ? ; _diffrn_ambient_temperature 150(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 'CCD area detector' _diffrn_measurement_method 'phi and omega scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 10745 _diffrn_reflns_av_R_equivalents 0.0346 _diffrn_reflns_av_sigmaI/netI 0.0319 _diffrn_reflns_limit_h_min -17 _diffrn_reflns_limit_h_max 17 _diffrn_reflns_limit_k_min -31 _diffrn_reflns_limit_k_max 32 _diffrn_reflns_limit_l_min -9 _diffrn_reflns_limit_l_max 9 _diffrn_reflns_theta_min 1.58 _diffrn_reflns_theta_max 26.38 _reflns_number_total 2939 _reflns_number_gt 2596 _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 ; The origin was fixed along the direction of the polar axis by applying a shift-limiting restraint the weighted sum of the coordinates. ; _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^)+(0.0338P)^2^+0.0000P] 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 mixed _refine_ls_extinction_method SHELXL _refine_ls_extinction_coef 0.0015(2) _refine_ls_extinction_expression 'Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^' _refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _refine_ls_abs_structure_Flack 0.5(10) _refine_ls_number_reflns 2939 _refine_ls_number_parameters 248 _refine_ls_number_restraints 1 _refine_ls_R_factor_all 0.0337 _refine_ls_R_factor_gt 0.0284 _refine_ls_wR_factor_ref 0.0606 _refine_ls_wR_factor_gt 0.0594 _refine_ls_goodness_of_fit_ref 0.969 _refine_ls_restrained_S_all 0.968 _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 N1 N 0.12389(8) 0.08718(5) 0.89300(15) 0.0313(3) Uani 1 1 d . . . O1 O 0.12808(8) 0.12522(4) 0.98549(14) 0.0474(3) Uani 1 1 d . . . O2 O 0.08675(8) 0.04614(4) 0.93281(15) 0.0469(3) Uani 1 1 d . . . N11 N 0.30280(7) 0.13633(4) 0.82709(14) 0.0248(2) Uani 1 1 d . . . C21 C 0.33299(8) 0.18766(5) 0.84511(17) 0.0247(3) Uani 1 1 d . . . C31 C 0.31136(10) 0.23089(5) 0.7461(2) 0.0319(3) Uani 1 1 d . . . H31 H 0.2686(11) 0.2282(5) 0.6488(19) 0.042(5) Uiso 1 1 d . . . C41 C 0.35242(11) 0.27747(6) 0.7922(2) 0.0381(4) Uani 1 1 d . . . H41 H 0.3368(10) 0.3092(6) 0.725(2) 0.039(4) Uiso 1 1 d . . . C51 C 0.41226(11) 0.28109(6) 0.9319(2) 0.0394(4) Uani 1 1 d . . . H51 H 0.4414(10) 0.3148(6) 0.958(2) 0.040(4) Uiso 1 1 d . . . C61 C 0.43266(10) 0.23838(5) 1.0296(2) 0.0341(3) Uani 1 1 d . . . H61 H 0.4744(11) 0.2412(5) 1.128(2) 0.043(5) Uiso 1 1 d . . . C71 C 0.39252(8) 0.19051(5) 0.98678(16) 0.0260(3) Uani 1 1 d . . . C81 C 0.39927(9) 0.13876(5) 1.05717(16) 0.0250(3) Uani 1 1 d . . . C91 C 0.44944(9) 0.11677(6) 1.19157(18) 0.0299(3) Uani 1 1 d . . . H91 H 0.4856(11) 0.1402(5) 1.2601(18) 0.033(4) Uiso 1 1 d . . . C101 C 0.44258(10) 0.06418(6) 1.22149(18) 0.0318(3) Uani 1 1 d . . . H101 H 0.4755(10) 0.0484(5) 1.318(2) 0.039(4) Uiso 1 1 d . . . C111 C 0.38678(9) 0.03258(6) 1.11815(17) 0.0294(3) Uani 1 1 d . . . H111 H 0.3821(9) -0.0043(7) 1.1403(19) 0.034(4) Uiso 1 1 d . . . C121 C 0.33585(9) 0.05306(5) 0.98345(17) 0.0255(3) Uani 1 1 d . . . H121 H 0.2977(8) 0.0296(5) 0.9144(17) 0.019(3) Uiso 1 1 d . . . C131 C 0.34301(8) 0.10631(5) 0.95529(16) 0.0229(3) Uani 1 1 d . . . C141 C 0.24729(9) 0.11674(5) 0.69213(16) 0.0230(3) Uani 1 1 d . . . C151 C 0.16346(9) 0.09098(5) 0.72043(16) 0.0255(3) Uani 1 1 d . . . C161 C 0.11354(10) 0.06817(6) 0.58986(19) 0.0329(3) Uani 1 1 d . . . H161 H 0.0530(10) 0.0506(5) 0.6125(18) 0.034(4) Uiso 1 1 d . . . C171 C 0.14571(11) 0.07298(5) 0.42529(19) 0.0336(3) Uani 1 1 d . . . H171 H 0.1131(11) 0.0578(6) 0.334(3) 0.050(5) Uiso 1 1 d . . . C181 C 0.22838(10) 0.09905(5) 0.39341(18) 0.0312(3) Uani 1 1 d . . . H181 H 0.2536(10) 0.1036(6) 0.277(2) 0.036(4) Uiso 1 1 d . . . C191 C 0.27942(9) 0.12017(5) 0.52585(18) 0.0280(3) Uani 1 1 d . . . H191 H 0.3387(10) 0.1385(5) 0.5064(19) 0.033(4) 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 N1 0.0266(6) 0.0404(7) 0.0268(7) 0.0026(6) 0.0021(5) 0.0025(5) O1 0.0511(7) 0.0607(7) 0.0304(6) -0.0149(6) 0.0087(5) -0.0064(5) O2 0.0454(6) 0.0456(6) 0.0497(7) 0.0130(5) 0.0190(5) -0.0026(5) N11 0.0279(6) 0.0257(6) 0.0209(6) 0.0015(5) -0.0031(5) -0.0021(4) C21 0.0233(6) 0.0256(7) 0.0253(7) -0.0007(6) 0.0036(6) 0.0004(5) C31 0.0349(8) 0.0294(8) 0.0314(8) 0.0011(6) 0.0036(7) 0.0021(6) C41 0.0461(10) 0.0277(8) 0.0406(9) 0.0017(7) 0.0093(7) 0.0027(7) C51 0.0416(8) 0.0278(8) 0.0487(10) -0.0086(7) 0.0068(7) -0.0067(7) C61 0.0319(8) 0.0351(9) 0.0351(8) -0.0094(7) 0.0017(7) -0.0043(6) C71 0.0237(6) 0.0298(7) 0.0244(7) -0.0050(6) 0.0037(5) 0.0013(5) C81 0.0211(6) 0.0331(7) 0.0208(7) -0.0038(6) 0.0018(5) 0.0003(5) C91 0.0237(7) 0.0429(9) 0.0231(7) -0.0041(7) -0.0011(6) 0.0021(6) C101 0.0268(8) 0.0455(9) 0.0229(8) 0.0052(7) -0.0007(6) 0.0082(6) C111 0.0303(8) 0.0311(8) 0.0268(7) 0.0046(6) 0.0046(6) 0.0063(6) C121 0.0249(7) 0.0298(7) 0.0220(7) -0.0021(6) 0.0038(6) -0.0003(5) C131 0.0219(6) 0.0290(7) 0.0178(6) -0.0011(5) 0.0019(5) 0.0023(5) C141 0.0248(6) 0.0235(7) 0.0208(7) -0.0003(5) -0.0026(5) 0.0029(5) C151 0.0277(7) 0.0268(7) 0.0220(7) 0.0010(5) 0.0010(6) 0.0018(6) C161 0.0303(8) 0.0347(8) 0.0339(9) -0.0015(6) -0.0056(7) -0.0035(6) C171 0.0378(8) 0.0350(8) 0.0279(8) -0.0063(7) -0.0096(6) 0.0008(6) C181 0.0391(8) 0.0349(8) 0.0195(7) -0.0009(6) -0.0003(6) 0.0072(6) C191 0.0285(7) 0.0301(7) 0.0253(7) 0.0011(6) 0.0021(6) 0.0009(6) _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 N1 O1 1.2214(16) . ? N1 O2 1.2240(16) . ? N1 C151 1.473(2) . ? N11 C131 1.3947(17) . ? N11 C21 1.3978(17) . ? N11 C141 1.4187(18) . ? C21 C31 1.393(2) . ? C21 C71 1.4047(19) . ? C31 C41 1.384(2) . ? C41 C51 1.396(2) . ? C51 C61 1.373(2) . ? C61 C71 1.4014(19) . ? C71 C81 1.4460(19) . ? C81 C91 1.398(2) . ? C81 C131 1.4106(19) . ? C91 C101 1.378(2) . ? C101 C111 1.401(2) . ? C111 C121 1.390(2) . ? C121 C131 1.393(2) . ? C141 C191 1.3884(19) . ? C141 C151 1.390(2) . ? C151 C161 1.382(2) . ? C161 C171 1.379(2) . ? C171 C181 1.385(2) . ? C181 C191 1.384(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 O1 N1 O2 124.18(13) . . ? O1 N1 C151 118.39(12) . . ? O2 N1 C151 117.40(12) . . ? C131 N11 C21 108.85(11) . . ? C131 N11 C141 125.08(11) . . ? C21 N11 C141 125.84(10) . . ? C31 C21 N11 129.06(13) . . ? C31 C21 C71 122.42(13) . . ? N11 C21 C71 108.52(11) . . ? C41 C31 C21 116.86(15) . . ? C31 C41 C51 121.65(15) . . ? C61 C51 C41 121.15(15) . . ? C51 C61 C71 118.86(15) . . ? C61 C71 C21 119.06(13) . . ? C61 C71 C81 133.72(14) . . ? C21 C71 C81 107.21(11) . . ? C91 C81 C131 118.88(12) . . ? C91 C81 C71 134.19(12) . . ? C131 C81 C71 106.89(12) . . ? C101 C91 C81 119.38(13) . . ? C91 C101 C111 120.85(13) . . ? C121 C111 C101 121.41(14) . . ? C111 C121 C131 117.13(13) . . ? C121 C131 N11 129.06(12) . . ? C121 C131 C81 122.36(12) . . ? N11 C131 C81 108.53(11) . . ? C191 C141 C151 117.87(12) . . ? C191 C141 N11 119.68(12) . . ? C151 C141 N11 122.32(12) . . ? C161 C151 C141 122.10(13) . . ? C161 C151 N1 117.12(12) . . ? C141 C151 N1 120.78(12) . . ? C171 C161 C151 119.02(14) . . ? C161 C171 C181 119.97(14) . . ? C191 C181 C171 120.45(14) . . ? C181 C191 C141 120.52(13) . . ? _diffrn_measured_fraction_theta_max 0.999 _diffrn_reflns_theta_full 26.38 _diffrn_measured_fraction_theta_full 0.999 _refine_diff_density_max 0.148 _refine_diff_density_min -0.116 _refine_diff_density_rms 0.029 data_3 _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C17 H15 N O2' _chemical_formula_sum 'C17 H15 N O2' _chemical_formula_weight 265.30 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 P21/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 7.3474(6) _cell_length_b 7.9170(7) _cell_length_c 23.9413(19) _cell_angle_alpha 90.00 _cell_angle_beta 92.5930(10) _cell_angle_gamma 90.00 _cell_volume 1391.2(2) _cell_formula_units_Z 4 _cell_measurement_temperature 150(2) _cell_measurement_reflns_used 3869 _cell_measurement_theta_min 2.5 _cell_measurement_theta_max 26.5 _exptl_crystal_description block _exptl_crystal_colour Colourless _exptl_crystal_size_max 0.24 _exptl_crystal_size_mid 0.24 _exptl_crystal_size_min 0.16 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.267 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 560 _exptl_absorpt_coefficient_mu 0.083 _exptl_absorpt_correction_type Multiscan _exptl_absorpt_correction_T_min 0.928 _exptl_absorpt_correction_T_max 0.464 _exptl_absorpt_process_details Sadabs _exptl_special_details ; ? ; _diffrn_ambient_temperature 150(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 'CCD area detector' _diffrn_measurement_method 'phi and omega scans' _diffrn_detector_area_resol_mean ? _diffrn_reflns_number 7632 _diffrn_reflns_av_R_equivalents 0.0214 _diffrn_reflns_av_sigmaI/netI 0.0292 _diffrn_reflns_limit_h_min -9 _diffrn_reflns_limit_h_max 9 _diffrn_reflns_limit_k_min -8 _diffrn_reflns_limit_k_max 9 _diffrn_reflns_limit_l_min -29 _diffrn_reflns_limit_l_max 22 _diffrn_reflns_theta_min 1.70 _diffrn_reflns_theta_max 26.37 _reflns_number_total 2830 _reflns_number_gt 2166 _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, 2008)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _refine_special_details ; Equivalent bond distances and angles within the two part weight components of the disordered moiety were restrained to be equal. A common overall isotropic dispalcement parameter was refined for the minor weight component with the exception of C15'. The adps of C15 and C15', the site of which are very closely situated, were constarined to be equal. ; _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^)+(0.0659P)^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 0 _refine_ls_number_reflns 2830 _refine_ls_number_parameters 232 _refine_ls_number_restraints 43 _refine_ls_R_factor_all 0.0487 _refine_ls_R_factor_gt 0.0392 _refine_ls_wR_factor_ref 0.1045 _refine_ls_wR_factor_gt 0.1012 _refine_ls_goodness_of_fit_ref 0.958 _refine_ls_restrained_S_all 0.960 _refine_ls_shift/su_max 0.003 _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 N1 N 0.30290(16) 0.87423(14) 0.15052(5) 0.0280(3) Uani 0.90 1 d PD A 1 C2 C 0.1946(2) 0.8051(2) 0.19060(7) 0.0290(4) Uani 0.90 1 d PD A 1 H2 H 0.0770 0.8450 0.1990 0.035 Uiso 0.90 1 calc PR A 1 C3 C 0.28065(19) 0.67193(17) 0.21618(5) 0.0302(3) Uani 0.90 1 d PD A 1 C31 C 0.2124(3) 0.5670(2) 0.26286(8) 0.0451(4) Uani 0.90 1 d PD A 1 H31A H 0.0894 0.6038 0.2714 0.068 Uiso 0.90 1 calc PR A 1 H31B H 0.2938 0.5806 0.2961 0.068 Uiso 0.90 1 calc PR A 1 H31C H 0.2095 0.4479 0.2517 0.068 Uiso 0.90 1 calc PR A 1 C4 C 0.4530(3) 0.6548(3) 0.19075(11) 0.0269(3) Uani 0.90 1 d PD A 1 C5 C 0.6004(2) 0.54437(18) 0.19926(6) 0.0345(3) Uani 0.90 1 d PD A 1 H5 H 0.5971 0.4576 0.2266 0.041 Uiso 0.90 1 calc PR A 1 C6 C 0.7500(2) 0.5635(3) 0.16736(10) 0.0392(5) Uani 0.90 1 d PD A 1 H6 H 0.8505 0.4890 0.1729 0.047 Uiso 0.90 1 calc PR A 1 C7 C 0.7571(2) 0.69091(19) 0.12685(6) 0.0366(4) Uani 0.90 1 d PD A 1 H7 H 0.8624 0.7013 0.1055 0.044 Uiso 0.90 1 calc PR A 1 C8 C 0.6135(2) 0.8017(3) 0.11743(8) 0.0314(4) Uani 0.90 1 d PD A 1 H8 H 0.6177 0.8881 0.0900 0.038 Uiso 0.90 1 calc PR A 1 C9 C 0.46296(19) 0.78134(18) 0.14980(5) 0.0272(3) Uani 0.90 1 d PD A 1 C10 C 0.25790(19) 1.01850(18) 0.11713(6) 0.0274(4) Uani 0.90 1 d PD A 1 C11 C 0.2414(2) 1.1744(2) 0.14306(7) 0.0340(4) Uani 0.90 1 d PD A 1 H11 H 0.2589 1.1828 0.1825 0.041 Uiso 0.90 1 calc PR A 1 C12 C 0.1999(4) 1.3173(3) 0.11189(12) 0.0362(4) Uani 0.90 1 d PD A 1 H12 H 0.1870 1.4230 0.1300 0.043 Uiso 0.90 1 calc PR A 1 C13 C 0.1770(5) 1.3066(3) 0.05428(12) 0.0342(4) Uani 0.90 1 d PD A 1 H13 H 0.1487 1.4049 0.0329 0.041 Uiso 0.90 1 calc PR A 1 C14 C 0.1954(5) 1.1527(3) 0.02798(10) 0.0296(4) Uani 0.90 1 d PD A 1 H14 H 0.1795 1.1455 -0.0115 0.036 Uiso 0.90 1 calc PR A 1 C15 C 0.2370(5) 1.0085(2) 0.05897(11) 0.0275(5) Uani 0.90 1 d PD A 1 O16 O 0.18718(14) 0.70883(12) 0.04718(4) 0.0441(3) Uani 1 1 d . A . C16 C 0.24415(17) 0.83975(16) 0.02935(5) 0.0322(3) Uani 1 1 d . . . O17 O 0.31833(13) 0.85532(12) -0.02034(4) 0.0432(3) Uani 1 1 d . A . C18 C 0.3266(2) 0.7025(2) -0.05329(7) 0.0539(4) Uani 1 1 d . . . H18A H 0.3959 0.6163 -0.0321 0.081 Uiso 1 1 calc R A . H18B H 0.3865 0.7265 -0.0881 0.081 Uiso 1 1 calc R . . H18C H 0.2028 0.6612 -0.0620 0.081 Uiso 1 1 calc R . . N1' N 0.398(2) 0.867(2) 0.1363(6) 0.069(2) Uiso 0.10 1 d PD A 2 C2' C 0.569(3) 0.805(4) 0.1237(13) 0.069(2) Uiso 0.10 1 d PD A 2 H2' H 0.6400 0.8508 0.0951 0.083 Uiso 0.10 1 calc PR A 2 C3' C 0.623(2) 0.676(2) 0.1559(7) 0.069(2) Uiso 0.10 1 d PD A 2 C31' C 0.794(3) 0.576(5) 0.1599(16) 0.069(2) Uiso 0.10 1 d PD A 2 H31D H 0.7835 0.4870 0.1879 0.103 Uiso 0.10 1 calc PR A 2 H31E H 0.8960 0.6510 0.1710 0.103 Uiso 0.10 1 calc PR A 2 H31F H 0.8163 0.5258 0.1235 0.103 Uiso 0.10 1 calc PR A 2 C4' C 0.471(4) 0.644(5) 0.1911(17) 0.069(2) Uiso 0.10 1 d PD A 2 C5' C 0.437(2) 0.531(2) 0.2334(7) 0.069(2) Uiso 0.10 1 d PD A 2 H5' H 0.5284 0.4512 0.2440 0.083 Uiso 0.10 1 calc PR A 2 C6' C 0.274(3) 0.530(3) 0.2611(11) 0.069(2) Uiso 0.10 1 d PD A 2 H6' H 0.2506 0.4495 0.2894 0.083 Uiso 0.10 1 calc PR A 2 C7' C 0.146(2) 0.655(2) 0.2444(8) 0.069(2) Uiso 0.10 1 d PD A 2 H7' H 0.0343 0.6603 0.2626 0.083 Uiso 0.10 1 calc PR A 2 C8' C 0.179(3) 0.770(4) 0.2023(12) 0.069(2) Uiso 0.10 1 d PD A 2 H8' H 0.0862 0.8474 0.1903 0.083 Uiso 0.10 1 calc PR A 2 C9' C 0.342(2) 0.772(2) 0.1785(7) 0.069(2) Uiso 0.10 1 d PD A 2 C10' C 0.308(3) 1.006(2) 0.1074(9) 0.069(2) Uiso 0.10 1 d PD A 2 C11' C 0.287(4) 1.152(3) 0.1370(11) 0.069(2) Uiso 0.10 1 d PD A 2 H11' H 0.3154 1.1524 0.1761 0.083 Uiso 0.10 1 calc PR A 2 C12' C 0.224(6) 1.298(4) 0.1112(16) 0.069(2) Uiso 0.10 1 d PD A 2 H12' H 0.2155 1.4019 0.1306 0.083 Uiso 0.10 1 calc PR A 2 C13' C 0.174(7) 1.282(4) 0.0544(16) 0.069(2) Uiso 0.10 1 d PD A 2 H13' H 0.1182 1.3732 0.0345 0.083 Uiso 0.10 1 calc PR A 2 C14' C 0.207(8) 1.133(4) 0.0281(14) 0.069(2) Uiso 0.10 1 d PD A 2 H14' H 0.2140 1.1366 -0.0114 0.083 Uiso 0.10 1 calc PR A 2 C15' C 0.232(6) 0.975(3) 0.0533(11) 0.0275(5) Uani 0.10 1 d PD A 2 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 N1 0.0300(6) 0.0274(6) 0.0265(6) 0.0025(5) 0.0023(5) 0.0038(5) C2 0.0305(8) 0.0287(9) 0.0280(9) -0.0025(6) 0.0025(6) -0.0005(6) C3 0.0360(8) 0.0293(8) 0.0254(7) -0.0015(6) 0.0016(6) -0.0041(6) C31 0.0523(12) 0.0410(11) 0.0425(9) 0.0130(8) 0.0084(9) -0.0002(9) C4 0.0325(8) 0.0245(8) 0.0233(6) -0.0016(5) -0.0053(6) -0.0016(6) C5 0.0418(8) 0.0307(8) 0.0302(7) 0.0022(6) -0.0061(6) 0.0033(7) C6 0.0375(11) 0.0388(10) 0.0404(11) -0.0024(8) -0.0083(9) 0.0121(10) C7 0.0323(8) 0.0444(9) 0.0333(8) -0.0037(6) 0.0031(6) 0.0031(7) C8 0.0342(9) 0.0330(8) 0.0271(8) 0.0014(6) 0.0020(7) 0.0002(7) C9 0.0296(7) 0.0267(7) 0.0250(7) -0.0030(5) -0.0019(6) 0.0005(6) C10 0.0280(8) 0.0234(7) 0.0306(8) -0.0003(6) 0.0009(6) 0.0012(6) C11 0.0373(11) 0.0322(9) 0.0325(8) -0.0070(6) 0.0007(7) 0.0023(7) C12 0.0342(12) 0.0229(8) 0.0515(9) -0.0081(7) 0.0013(8) 0.0032(7) C13 0.0329(8) 0.0215(9) 0.0481(9) 0.0061(7) -0.0006(7) 0.0016(8) C14 0.0306(9) 0.0261(9) 0.0322(7) 0.0039(7) 0.0011(6) 0.0013(7) C15 0.0298(7) 0.0211(12) 0.0314(9) -0.0016(8) -0.0006(7) -0.0014(11) O16 0.0620(7) 0.0267(5) 0.0430(6) 0.0010(4) -0.0031(5) -0.0039(5) C16 0.0336(7) 0.0284(7) 0.0339(7) 0.0012(5) -0.0050(5) 0.0007(6) O17 0.0481(6) 0.0380(6) 0.0442(6) -0.0101(4) 0.0107(5) -0.0050(5) C18 0.0525(9) 0.0529(10) 0.0571(10) -0.0258(8) 0.0119(8) -0.0049(8) C15' 0.0298(7) 0.0211(12) 0.0314(9) -0.0016(8) -0.0006(7) -0.0014(11) _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 N1 C2 1.3867(19) . ? N1 C9 1.3878(17) . ? N1 C10 1.4244(17) . ? C2 C3 1.360(2) . ? C3 C4 1.436(2) . ? C3 C31 1.497(2) . ? C4 C5 1.399(2) . ? C4 C9 1.406(2) . ? C5 C6 1.375(2) . ? C6 C7 1.402(3) . ? C7 C8 1.383(2) . ? C8 C9 1.388(2) . ? C10 C11 1.389(2) . ? C10 C15 1.396(3) . ? C11 C12 1.382(2) . ? C12 C13 1.385(2) . ? C13 C14 1.380(2) . ? C14 C15 1.388(2) . ? C15 C16 1.515(2) . ? O16 C16 1.2033(15) . ? C16 C15' 1.22(2) . ? C16 O17 1.3365(16) . ? O17 C18 1.4472(16) . ? N1' C9' 1.344(14) . ? N1' C2' 1.392(17) . ? N1' C10' 1.444(15) . ? C2' C3' 1.330(17) . ? C3' C4' 1.447(17) . ? C3' C31' 1.486(17) . ? C4' C5' 1.383(16) . ? C4' C9' 1.411(16) . ? C5' C6' 1.395(16) . ? C6' C7' 1.409(16) . ? C7' C8' 1.387(17) . ? C8' C9' 1.351(16) . ? C10' C11' 1.365(16) . ? C10' C15' 1.409(17) . ? C11' C12' 1.382(17) . ? C12' C13' 1.397(18) . ? C13' C14' 1.366(18) . ? C14' C15' 1.392(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 N1 C9 108.20(12) . . ? C2 N1 C10 125.39(12) . . ? C9 N1 C10 126.40(12) . . ? C3 C2 N1 110.37(14) . . ? C2 C3 C4 106.45(13) . . ? C2 C3 C31 126.98(14) . . ? C4 C3 C31 126.54(14) . . ? C5 C4 C9 118.84(16) . . ? C5 C4 C3 133.53(15) . . ? C9 C4 C3 107.63(14) . . ? C6 C5 C4 118.88(15) . . ? C5 C6 C7 121.30(16) . . ? C8 C7 C6 121.13(14) . . ? C7 C8 C9 117.17(15) . . ? N1 C9 C8 129.95(14) . . ? N1 C9 C4 107.35(13) . . ? C8 C9 C4 122.68(14) . . ? C11 C10 C15 119.21(14) . . ? C11 C10 N1 118.97(13) . . ? C15 C10 N1 121.77(13) . . ? C12 C11 C10 120.50(16) . . ? C11 C12 C13 120.12(16) . . ? C14 C13 C12 119.89(16) . . ? C13 C14 C15 120.37(18) . . ? C14 C15 C10 119.87(16) . . ? C14 C15 C16 119.13(19) . . ? C10 C15 C16 120.81(17) . . ? O16 C16 C15' 123.7(18) . . ? O16 C16 O17 123.88(12) . . ? C15' C16 O17 112.3(18) . . ? O16 C16 C15 125.02(18) . . ? C15' C16 C15 2(2) . . ? O17 C16 C15 111.08(16) . . ? C16 O17 C18 115.90(11) . . ? C9' N1' C2' 106.0(14) . . ? C9' N1' C10' 129.7(16) . . ? C2' N1' C10' 124.3(16) . . ? C3' C2' N1' 113.1(17) . . ? C2' C3' C4' 104.8(14) . . ? C2' C3' C31' 132.4(18) . . ? C4' C3' C31' 122.8(17) . . ? C5' C4' C9' 118.3(16) . . ? C5' C4' C3' 135.2(17) . . ? C9' C4' C3' 106.3(13) . . ? C4' C5' C6' 123.0(17) . . ? C5' C6' C7' 115.6(17) . . ? C8' C7' C6' 122.4(17) . . ? C9' C8' C7' 119.8(18) . . ? N1' C9' C8' 129.3(16) . . ? N1' C9' C4' 109.5(13) . . ? C8' C9' C4' 120.4(15) . . ? C11' C10' C15' 124.9(17) . . ? C11' C10' N1' 117.0(18) . . ? C15' C10' N1' 117.6(17) . . ? C10' C11' C12' 121(2) . . ? C11' C12' C13' 115(2) . . ? C14' C13' C12' 119(2) . . ? C13' C14' C15' 127(3) . . ? C16 C15' C14' 126(2) . . ? C16 C15' C10' 123(2) . . ? C14' C15' C10' 106.5(19) . . ? _diffrn_measured_fraction_theta_max 0.995 _diffrn_reflns_theta_full 26.37 _diffrn_measured_fraction_theta_full 0.995 _refine_diff_density_max 0.230 _refine_diff_density_min -0.237 _refine_diff_density_rms 0.062 data_4 _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C14 H10 N2 O2' _chemical_formula_sum 'C14 H10 N2 O2' _chemical_formula_weight 238.24 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 Orthorhombic _symmetry_space_group_name_H-M Pbca loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, -y, z+1/2' '-x, y+1/2, -z+1/2' 'x+1/2, -y+1/2, -z' '-x, -y, -z' 'x-1/2, y, -z-1/2' 'x, -y-1/2, z-1/2' '-x-1/2, y-1/2, z' _cell_length_a 7.7628(6) _cell_length_b 7.7446(6) _cell_length_c 38.063(3) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 2288.3(3) _cell_formula_units_Z 8 _cell_measurement_temperature 150(2) _cell_measurement_reflns_used 4033 _cell_measurement_theta_min 2.8 _cell_measurement_theta_max 25.7 _exptl_crystal_description Tablet _exptl_crystal_colour Brown _exptl_crystal_size_max 0.51 _exptl_crystal_size_mid 0.39 _exptl_crystal_size_min 0.12 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.383 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 992 _exptl_absorpt_coefficient_mu 0.095 _exptl_absorpt_correction_type multiscan _exptl_absorpt_correction_T_min 0.754 _exptl_absorpt_correction_T_max 0.928 _exptl_absorpt_process_details sadabs _exptl_special_details ; ? ; _diffrn_ambient_temperature 150(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 'CCD area detector' _diffrn_measurement_method 'phi and omega scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 11920 _diffrn_reflns_av_R_equivalents 0.0303 _diffrn_reflns_av_sigmaI/netI 0.0228 _diffrn_reflns_limit_h_min -9 _diffrn_reflns_limit_h_max 8 _diffrn_reflns_limit_k_min -8 _diffrn_reflns_limit_k_max 9 _diffrn_reflns_limit_l_min -47 _diffrn_reflns_limit_l_max 45 _diffrn_reflns_theta_min 2.14 _diffrn_reflns_theta_max 26.40 _reflns_number_total 2343 _reflns_number_gt 1945 _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^)+(0.0524P)^2^+0.5998P] 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 mixed _refine_ls_extinction_method SHELXL _refine_ls_extinction_coef 0.0039(8) _refine_ls_extinction_expression 'Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^' _refine_ls_number_reflns 2343 _refine_ls_number_parameters 204 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0522 _refine_ls_R_factor_gt 0.0424 _refine_ls_wR_factor_ref 0.1042 _refine_ls_wR_factor_gt 0.1001 _refine_ls_goodness_of_fit_ref 1.044 _refine_ls_restrained_S_all 1.044 _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 N1 N -0.05577(15) 0.17171(16) 0.62670(3) 0.0257(3) Uani 1 1 d . . . C2 C 0.09053(19) 0.2758(2) 0.62548(4) 0.0304(3) Uani 1 1 d . . . H2 H 0.112(2) 0.341(2) 0.6049(4) 0.028(4) Uiso 1 1 d . . . C3 C 0.1736(2) 0.2701(2) 0.65634(4) 0.0347(4) Uani 1 1 d . . . H3 H 0.274(3) 0.329(3) 0.6619(5) 0.048(5) Uiso 1 1 d . . . C4 C 0.07977(19) 0.15690(19) 0.67904(4) 0.0302(4) Uani 1 1 d . . . C5 C 0.1038(2) 0.0974(2) 0.71339(4) 0.0388(4) Uani 1 1 d . . . H5 H 0.202(2) 0.133(2) 0.7261(4) 0.040(5) Uiso 1 1 d . . . C6 C -0.0104(2) -0.0194(2) 0.72715(4) 0.0424(4) Uani 1 1 d . . . H6 H 0.007(2) -0.060(2) 0.7507(5) 0.039(4) Uiso 1 1 d . . . C7 C -0.1502(2) -0.0790(2) 0.70756(4) 0.0377(4) Uani 1 1 d . . . H7 H -0.229(2) -0.162(2) 0.7175(5) 0.045(5) Uiso 1 1 d . . . C8 C -0.1798(2) -0.0215(2) 0.67381(4) 0.0298(3) Uani 1 1 d . . . H8 H -0.277(2) -0.061(2) 0.6604(4) 0.033(4) Uiso 1 1 d . . . C9 C -0.06339(18) 0.09697(19) 0.65994(4) 0.0263(3) Uani 1 1 d . . . C10 C -0.17699(18) 0.15028(18) 0.59947(4) 0.0248(3) Uani 1 1 d . . . C11 C -0.35167(19) 0.16514(19) 0.60668(4) 0.0285(3) Uani 1 1 d . . . H11 H -0.391(2) 0.188(2) 0.6296(4) 0.029(4) Uiso 1 1 d . . . C12 C -0.4723(2) 0.1508(2) 0.58032(4) 0.0329(4) Uani 1 1 d . . . H12 H -0.593(2) 0.159(2) 0.5860(4) 0.032(4) Uiso 1 1 d . . . C13 C -0.4227(2) 0.1266(2) 0.54595(4) 0.0374(4) Uani 1 1 d . . . H13 H -0.505(2) 0.118(2) 0.5276(5) 0.045(5) Uiso 1 1 d . . . C14 C -0.2503(2) 0.1141(2) 0.53792(4) 0.0361(4) Uani 1 1 d . . . H14 H -0.211(2) 0.095(2) 0.5148(5) 0.042(5) Uiso 1 1 d . . . C15 C -0.12997(18) 0.12212(19) 0.56461(4) 0.0277(3) Uani 1 1 d . . . N111 N 0.05010(16) 0.09196(18) 0.55476(3) 0.0340(3) Uani 1 1 d . . . O111 O 0.10159(17) 0.1555(2) 0.52739(3) 0.0595(4) Uani 1 1 d . . . O112 O 0.13815(14) 0.00100(15) 0.57377(3) 0.0402(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 N1 0.0219(6) 0.0253(6) 0.0301(6) 0.0015(5) -0.0002(5) -0.0026(5) C2 0.0250(7) 0.0248(8) 0.0416(9) 0.0013(7) 0.0009(6) -0.0030(6) C3 0.0258(8) 0.0298(9) 0.0485(9) -0.0075(7) -0.0060(7) -0.0026(6) C4 0.0292(8) 0.0257(8) 0.0356(8) -0.0068(6) -0.0042(6) 0.0053(6) C5 0.0411(9) 0.0409(10) 0.0344(8) -0.0099(7) -0.0109(8) 0.0086(8) C6 0.0530(11) 0.0468(11) 0.0273(8) 0.0016(7) -0.0019(8) 0.0102(9) C7 0.0431(10) 0.0377(10) 0.0323(8) 0.0033(7) 0.0071(7) 0.0038(8) C8 0.0317(8) 0.0287(8) 0.0290(7) -0.0024(6) 0.0026(6) -0.0001(6) C9 0.0273(7) 0.0237(7) 0.0278(7) -0.0025(6) -0.0005(6) 0.0046(6) C10 0.0234(7) 0.0200(7) 0.0310(7) 0.0033(6) -0.0013(6) -0.0001(5) C11 0.0254(8) 0.0254(8) 0.0346(8) -0.0001(6) 0.0026(6) -0.0006(6) C12 0.0223(8) 0.0278(8) 0.0486(9) 0.0019(7) -0.0020(7) 0.0008(6) C13 0.0321(9) 0.0383(10) 0.0417(9) 0.0025(7) -0.0122(7) 0.0006(7) C14 0.0382(9) 0.0404(9) 0.0297(8) 0.0022(7) -0.0032(7) 0.0015(7) C15 0.0243(7) 0.0274(8) 0.0313(8) 0.0041(6) 0.0021(6) 0.0010(6) N111 0.0289(7) 0.0374(8) 0.0356(7) -0.0016(6) 0.0044(6) -0.0008(6) O111 0.0474(8) 0.0895(11) 0.0418(7) 0.0134(7) 0.0189(6) -0.0009(8) O112 0.0253(6) 0.0362(7) 0.0589(7) 0.0015(6) -0.0004(5) 0.0032(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 N1 C9 1.3928(18) . ? N1 C2 1.3934(19) . ? N1 C10 1.4097(18) . ? C2 C3 1.341(2) . ? C3 C4 1.430(2) . ? C4 C5 1.399(2) . ? C4 C9 1.407(2) . ? C5 C6 1.370(3) . ? C6 C7 1.396(2) . ? C7 C8 1.379(2) . ? C8 C9 1.391(2) . ? C10 C11 1.388(2) . ? C10 C15 1.393(2) . ? C11 C12 1.377(2) . ? C12 C13 1.376(2) . ? C13 C14 1.376(2) . ? C14 C15 1.382(2) . ? C15 N111 1.4660(19) . ? N111 O112 1.2193(16) . ? N111 O111 1.2196(17) . ? 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 C9 N1 C2 107.77(12) . . ? C9 N1 C10 126.21(12) . . ? C2 N1 C10 125.99(12) . . ? C3 C2 N1 110.12(14) . . ? C2 C3 C4 107.71(14) . . ? C5 C4 C9 118.67(15) . . ? C5 C4 C3 134.31(15) . . ? C9 C4 C3 107.01(13) . . ? C6 C5 C4 119.22(16) . . ? C5 C6 C7 121.15(16) . . ? C8 C7 C6 121.36(16) . . ? C7 C8 C9 117.28(15) . . ? C8 C9 N1 130.25(13) . . ? C8 C9 C4 122.31(14) . . ? N1 C9 C4 107.39(13) . . ? C11 C10 C15 117.20(13) . . ? C11 C10 N1 119.79(13) . . ? C15 C10 N1 122.94(13) . . ? C12 C11 C10 120.90(15) . . ? C13 C12 C11 120.87(15) . . ? C14 C13 C12 119.53(15) . . ? C13 C14 C15 119.40(15) . . ? C14 C15 C10 122.03(14) . . ? C14 C15 N111 116.70(13) . . ? C10 C15 N111 121.22(13) . . ? O112 N111 O111 123.79(14) . . ? O112 N111 C15 118.35(12) . . ? O111 N111 C15 117.82(13) . . ? _diffrn_measured_fraction_theta_max 0.997 _diffrn_reflns_theta_full 26.40 _diffrn_measured_fraction_theta_full 0.997 _refine_diff_density_max 0.223 _refine_diff_density_min -0.164 _refine_diff_density_rms 0.043 data_5 _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C15 H12 N2 O2' _chemical_formula_sum 'C15 H12 N2 O2' _chemical_formula_weight 252.27 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 P21/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 7.1962(8) _cell_length_b 7.8951(9) _cell_length_c 22.354(3) _cell_angle_alpha 90.00 _cell_angle_beta 95.317(2) _cell_angle_gamma 90.00 _cell_volume 1264.6(2) _cell_formula_units_Z 4 _cell_measurement_temperature 150(2) _cell_measurement_reflns_used 4025 _cell_measurement_theta_min 2.5 _cell_measurement_theta_max 26.5 _exptl_crystal_description block _exptl_crystal_colour Colourless _exptl_crystal_size_max 0.22 _exptl_crystal_size_mid 0.22 _exptl_crystal_size_min 0.18 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.325 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 528 _exptl_absorpt_coefficient_mu 0.090 _exptl_absorpt_correction_type multiscan _exptl_absorpt_correction_T_min 0.667 _exptl_absorpt_correction_T_max 1.000 _exptl_absorpt_process_details sadabs _exptl_special_details ; ? ; _diffrn_ambient_temperature 150(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 'CCD area detector' _diffrn_measurement_method 'phi and omega scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 6900 _diffrn_reflns_av_R_equivalents 0.0291 _diffrn_reflns_av_sigmaI/netI 0.0374 _diffrn_reflns_limit_h_min -8 _diffrn_reflns_limit_h_max 6 _diffrn_reflns_limit_k_min -9 _diffrn_reflns_limit_k_max 9 _diffrn_reflns_limit_l_min -20 _diffrn_reflns_limit_l_max 27 _diffrn_reflns_theta_min 1.83 _diffrn_reflns_theta_max 26.36 _reflns_number_total 2570 _reflns_number_gt 1942 _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^)+(0.0504P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geometric _refine_ls_hydrogen_treatment riding _refine_ls_extinction_method SHELXL _refine_ls_extinction_coef 0.0079(17) _refine_ls_extinction_expression 'Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^' _refine_ls_number_reflns 2570 _refine_ls_number_parameters 173 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0453 _refine_ls_R_factor_gt 0.0363 _refine_ls_wR_factor_ref 0.0896 _refine_ls_wR_factor_gt 0.0874 _refine_ls_goodness_of_fit_ref 0.937 _refine_ls_restrained_S_all 0.937 _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 N1 N 0.23258(14) 0.88980(13) 0.33777(4) 0.0308(3) Uani 1 1 d . . . C2 C 0.10579(18) 0.82046(17) 0.29535(6) 0.0364(3) Uani 1 1 d . . . H2 H -0.0152 0.8665 0.2857 0.044 Uiso 1 1 calc R . . N3 N 0.16514(16) 0.68565(14) 0.26921(5) 0.0407(3) Uani 1 1 d . . . C4 C 0.34642(18) 0.66328(15) 0.29584(5) 0.0335(3) Uani 1 1 d . . . C5 C 0.4796(2) 0.54148(17) 0.28489(6) 0.0408(3) Uani 1 1 d . . . H5 H 0.4526 0.4551 0.2558 0.049 Uiso 1 1 calc R . . C6 C 0.6511(2) 0.55021(17) 0.31744(6) 0.0429(4) Uani 1 1 d . . . H6 H 0.7431 0.4678 0.3108 0.051 Uiso 1 1 calc R . . C7 C 0.69318(19) 0.67755(17) 0.36009(6) 0.0409(3) Uani 1 1 d . . . H7 H 0.8135 0.6804 0.3815 0.049 Uiso 1 1 calc R . . C8 C 0.56352(18) 0.79894(16) 0.37169(6) 0.0356(3) Uani 1 1 d . . . H8 H 0.5912 0.8853 0.4007 0.043 Uiso 1 1 calc R . . C9 C 0.39069(17) 0.78870(15) 0.33885(5) 0.0295(3) Uani 1 1 d . . . C10 C 0.20419(16) 1.03407(15) 0.37437(5) 0.0296(3) Uani 1 1 d . . . C11 C 0.17514(17) 1.19021(16) 0.34683(6) 0.0361(3) Uani 1 1 d . . . H11 H 0.1732 1.1994 0.3044 0.043 Uiso 1 1 calc R . . C12 C 0.14890(17) 1.33256(16) 0.38103(6) 0.0388(3) Uani 1 1 d . . . H12 H 0.1266 1.4391 0.3620 0.047 Uiso 1 1 calc R . . C13 C 0.15500(17) 1.32035(16) 0.44288(6) 0.0362(3) Uani 1 1 d . . . H13 H 0.1377 1.4185 0.4663 0.043 Uiso 1 1 calc R . . C14 C 0.18621(17) 1.16533(15) 0.47048(6) 0.0320(3) Uani 1 1 d . . . H14 H 0.1917 1.1579 0.5130 0.038 Uiso 1 1 calc R . . C15 C 0.20982(16) 1.01985(15) 0.43704(5) 0.0276(3) Uani 1 1 d . . . O16 O 0.16786(13) 0.72090(11) 0.44738(4) 0.0398(3) Uani 1 1 d . . . C16 C 0.23033(16) 0.85259(15) 0.46771(6) 0.0299(3) Uani 1 1 d . . . O17 O 0.32431(12) 0.86712(11) 0.52208(4) 0.0395(3) Uani 1 1 d . . . C18 C 0.3467(2) 0.71317(18) 0.55696(7) 0.0485(4) Uani 1 1 d . . . H18A H 0.4164 0.7377 0.5957 0.073 Uiso 1 1 calc R . . H18B H 0.4152 0.6297 0.5351 0.073 Uiso 1 1 calc R . . H18C H 0.2236 0.6677 0.5637 0.073 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 N1 0.0304(6) 0.0312(6) 0.0304(6) -0.0010(5) 0.0007(4) 0.0006(4) C2 0.0331(7) 0.0410(8) 0.0341(7) -0.0005(6) -0.0014(5) -0.0030(6) N3 0.0413(7) 0.0431(7) 0.0373(6) -0.0062(5) 0.0011(5) -0.0045(5) C4 0.0393(8) 0.0335(7) 0.0283(7) 0.0013(5) 0.0071(5) -0.0044(6) C5 0.0540(9) 0.0359(8) 0.0345(7) -0.0058(6) 0.0144(6) -0.0006(6) C6 0.0465(9) 0.0425(9) 0.0417(8) 0.0024(7) 0.0148(6) 0.0114(6) C7 0.0370(8) 0.0475(9) 0.0384(8) 0.0034(7) 0.0047(6) 0.0065(6) C8 0.0369(8) 0.0372(8) 0.0324(7) -0.0011(6) 0.0017(5) 0.0017(6) C9 0.0336(7) 0.0279(7) 0.0278(6) 0.0031(5) 0.0067(5) -0.0001(5) C10 0.0238(6) 0.0288(7) 0.0357(7) 0.0003(5) 0.0001(5) -0.0005(5) C11 0.0331(7) 0.0363(8) 0.0384(7) 0.0090(6) 0.0003(5) 0.0019(5) C12 0.0328(7) 0.0266(7) 0.0566(9) 0.0109(6) 0.0023(6) 0.0032(5) C13 0.0300(7) 0.0255(7) 0.0532(9) -0.0040(6) 0.0050(6) 0.0011(5) C14 0.0273(7) 0.0309(7) 0.0376(7) -0.0023(6) 0.0019(5) -0.0005(5) C15 0.0234(6) 0.0253(7) 0.0337(7) 0.0004(5) 0.0011(5) 0.0000(5) O16 0.0530(6) 0.0256(5) 0.0412(5) -0.0008(4) 0.0072(4) -0.0040(4) C16 0.0281(7) 0.0289(7) 0.0335(7) -0.0006(6) 0.0068(5) 0.0014(5) O17 0.0413(6) 0.0363(5) 0.0391(5) 0.0094(4) -0.0059(4) -0.0041(4) C18 0.0405(8) 0.0494(9) 0.0542(9) 0.0253(7) -0.0039(7) -0.0031(6) _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 N1 C2 1.3678(15) . ? N1 C9 1.3882(15) . ? N1 C10 1.4282(15) . ? C2 N3 1.3050(16) . ? N3 C4 1.3940(17) . ? C4 C5 1.3953(18) . ? C4 C9 1.3963(16) . ? C5 C6 1.3746(19) . ? C6 C7 1.3993(18) . ? C7 C8 1.3789(18) . ? C8 C9 1.3868(18) . ? C10 C11 1.3851(16) . ? C10 C15 1.4022(17) . ? C11 C12 1.3821(18) . ? C12 C13 1.3825(19) . ? C13 C14 1.3796(17) . ? C14 C15 1.3893(17) . ? C15 C16 1.4890(17) . ? O16 C16 1.2049(14) . ? C16 O17 1.3399(15) . ? O17 C18 1.4450(15) . ? 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 N1 C9 105.95(10) . . ? C2 N1 C10 126.49(11) . . ? C9 N1 C10 127.53(10) . . ? N3 C2 N1 114.32(12) . . ? C2 N3 C4 104.14(10) . . ? N3 C4 C5 130.04(12) . . ? N3 C4 C9 110.42(11) . . ? C5 C4 C9 119.53(12) . . ? C6 C5 C4 118.04(12) . . ? C5 C6 C7 121.59(13) . . ? C8 C7 C6 121.32(13) . . ? C7 C8 C9 116.70(12) . . ? C8 C9 N1 132.00(11) . . ? C8 C9 C4 122.82(11) . . ? N1 C9 C4 105.16(11) . . ? C11 C10 C15 120.30(11) . . ? C11 C10 N1 118.61(11) . . ? C15 C10 N1 121.07(10) . . ? C12 C11 C10 120.03(12) . . ? C11 C12 C13 120.21(12) . . ? C14 C13 C12 119.86(12) . . ? C13 C14 C15 121.04(12) . . ? C14 C15 C10 118.53(11) . . ? C14 C15 C16 119.82(11) . . ? C10 C15 C16 121.56(11) . . ? O16 C16 O17 123.74(11) . . ? O16 C16 C15 125.03(11) . . ? O17 C16 C15 111.21(10) . . ? C16 O17 C18 116.05(10) . . ? _diffrn_measured_fraction_theta_max 0.995 _diffrn_reflns_theta_full 26.36 _diffrn_measured_fraction_theta_full 0.995 _refine_diff_density_max 0.183 _refine_diff_density_min -0.168 _refine_diff_density_rms 0.036 data_6 _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C14 H11 N3 O2' _chemical_formula_sum 'C14 H11 N3 O2' _chemical_formula_weight 253.26 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 Triclinic _symmetry_space_group_name_H-M P-1 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 7.7474(16) _cell_length_b 8.2529(18) _cell_length_c 10.230(2) _cell_angle_alpha 86.580(3) _cell_angle_beta 82.200(3) _cell_angle_gamma 71.914(3) _cell_volume 615.9(2) _cell_formula_units_Z 2 _cell_measurement_temperature 150(2) _cell_measurement_reflns_used 1775 _cell_measurement_theta_min 2.5 _cell_measurement_theta_max 26.5 _exptl_crystal_description block _exptl_crystal_colour Colourless _exptl_crystal_size_max 0.33 _exptl_crystal_size_mid 0.30 _exptl_crystal_size_min 0.18 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.366 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 264 _exptl_absorpt_coefficient_mu 0.095 _exptl_absorpt_correction_type multiscan _exptl_absorpt_correction_T_min 0.894 _exptl_absorpt_correction_T_max 1.000 _exptl_absorpt_process_details sadabs _exptl_special_details ; ? ; _diffrn_ambient_temperature 150(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 'CCD area detector' _diffrn_measurement_method 'phi and omega scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 4925 _diffrn_reflns_av_R_equivalents 0.0200 _diffrn_reflns_av_sigmaI/netI 0.0336 _diffrn_reflns_limit_h_min -9 _diffrn_reflns_limit_h_max 9 _diffrn_reflns_limit_k_min -10 _diffrn_reflns_limit_k_max 10 _diffrn_reflns_limit_l_min -12 _diffrn_reflns_limit_l_max 12 _diffrn_reflns_theta_min 2.01 _diffrn_reflns_theta_max 26.39 _reflns_number_total 2471 _reflns_number_gt 2040 _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^)+(0.0464P)^2^+0.2511P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens 'difmap except Me group, geometric' _refine_ls_hydrogen_treatment mixed _refine_ls_extinction_method none _refine_ls_extinction_coef 0 _refine_ls_number_reflns 2471 _refine_ls_number_parameters 205 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0668 _refine_ls_R_factor_gt 0.0522 _refine_ls_wR_factor_ref 0.1211 _refine_ls_wR_factor_gt 0.1151 _refine_ls_goodness_of_fit_ref 1.111 _refine_ls_restrained_S_all 1.111 _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 N1 N 0.03460(19) 0.95855(18) 0.80131(14) 0.0229(3) Uani 1 1 d . . . C2 C -0.0537(3) 0.8596(2) 0.88009(18) 0.0265(4) Uani 1 1 d . . . N3 N -0.2196(2) 0.9449(2) 0.92852(15) 0.0313(4) Uani 1 1 d . . . C4 C -0.2458(2) 1.1103(2) 0.87919(18) 0.0291(4) Uani 1 1 d . . . C5 C -0.3989(3) 1.2545(3) 0.8974(2) 0.0389(5) Uani 1 1 d . . . H5 H -0.505(3) 1.249(3) 0.952(2) 0.041(6) Uiso 1 1 d . . . C6 C -0.3863(3) 1.4040(3) 0.8359(2) 0.0428(6) Uani 1 1 d . . . H6 H -0.489(3) 1.505(3) 0.847(2) 0.046(6) Uiso 1 1 d . . . C7 C -0.2275(3) 1.4132(3) 0.7576(2) 0.0369(5) Uani 1 1 d . . . H7 H -0.224(3) 1.521(3) 0.715(2) 0.037(6) Uiso 1 1 d . . . C8 C -0.0743(3) 1.2716(2) 0.73736(19) 0.0297(4) Uani 1 1 d . . . H8 H 0.032(3) 1.277(2) 0.684(2) 0.029(5) Uiso 1 1 d . . . C9 C -0.0882(2) 1.1218(2) 0.79964(17) 0.0252(4) Uani 1 1 d . . . C10 C 0.2082(2) 0.9033(2) 0.72351(17) 0.0225(4) Uani 1 1 d . . . C11 C 0.3527(3) 0.9538(2) 0.75284(19) 0.0282(4) Uani 1 1 d . . . H11 H 0.335(3) 1.023(3) 0.829(2) 0.032(5) Uiso 1 1 d . . . C12 C 0.5209(3) 0.9000(3) 0.6771(2) 0.0313(5) Uani 1 1 d . . . H12 H 0.622(3) 0.934(3) 0.698(2) 0.047(6) Uiso 1 1 d . . . C13 C 0.5488(3) 0.7925(2) 0.5722(2) 0.0302(4) Uani 1 1 d . . . H13 H 0.660(3) 0.757(2) 0.522(2) 0.031(5) Uiso 1 1 d . . . C14 C 0.4078(3) 0.7375(2) 0.5435(2) 0.0306(4) Uani 1 1 d . . . H14 H 0.423(3) 0.664(3) 0.468(2) 0.038(6) Uiso 1 1 d . . . C15 C 0.2400(2) 0.7947(2) 0.61797(18) 0.0261(4) Uani 1 1 d . . . N15 N 0.0923(2) 0.7352(3) 0.58447(17) 0.0413(5) Uani 1 1 d . . . O15A O -0.0567(2) 0.8403(3) 0.57677(18) 0.0645(6) Uani 1 1 d . . . O15B O 0.1286(3) 0.5830(2) 0.56515(17) 0.0607(5) Uani 1 1 d . . . C16 C 0.0364(3) 0.6762(2) 0.9081(2) 0.0343(5) Uani 1 1 d . . . H16A H -0.0455 0.6323 0.9718 0.052 Uiso 1 1 calc R . . H16B H 0.1504 0.6630 0.9449 0.052 Uiso 1 1 calc R . . H16C H 0.0635 0.6125 0.8262 0.052 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 N1 0.0219(8) 0.0227(8) 0.0240(8) -0.0025(6) -0.0007(6) -0.0070(6) C2 0.0302(10) 0.0321(10) 0.0212(9) -0.0030(7) -0.0012(7) -0.0158(8) N3 0.0288(9) 0.0426(10) 0.0257(8) -0.0082(7) 0.0031(7) -0.0168(7) C4 0.0263(10) 0.0375(11) 0.0244(10) -0.0096(8) -0.0017(8) -0.0098(8) C5 0.0243(10) 0.0527(14) 0.0344(11) -0.0149(10) 0.0005(9) -0.0031(9) C6 0.0356(12) 0.0388(13) 0.0437(13) -0.0146(10) -0.0107(10) 0.0084(10) C7 0.0446(13) 0.0278(11) 0.0337(11) -0.0044(9) -0.0114(9) -0.0009(9) C8 0.0325(11) 0.0281(10) 0.0275(10) -0.0036(8) -0.0032(8) -0.0075(8) C9 0.0247(9) 0.0260(10) 0.0234(9) -0.0068(7) -0.0030(7) -0.0042(7) C10 0.0232(9) 0.0181(9) 0.0247(9) 0.0011(7) -0.0022(7) -0.0047(7) C11 0.0313(10) 0.0281(10) 0.0268(10) -0.0031(8) -0.0042(8) -0.0105(8) C12 0.0234(10) 0.0388(11) 0.0342(11) -0.0018(9) -0.0057(8) -0.0121(9) C13 0.0202(10) 0.0324(11) 0.0322(10) -0.0007(8) 0.0019(8) -0.0020(8) C14 0.0313(11) 0.0266(10) 0.0322(11) -0.0078(8) 0.0021(8) -0.0075(8) C15 0.0250(9) 0.0262(10) 0.0293(10) -0.0041(8) -0.0025(8) -0.0106(8) N15 0.0384(11) 0.0625(13) 0.0317(10) -0.0207(9) 0.0083(8) -0.0298(10) O15A 0.0234(8) 0.1125(16) 0.0609(11) -0.0460(11) 0.0037(7) -0.0212(9) O15B 0.0917(14) 0.0628(12) 0.0481(10) -0.0189(8) 0.0037(9) -0.0552(11) C16 0.0467(12) 0.0302(11) 0.0295(11) 0.0037(8) -0.0042(9) -0.0175(9) _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 N1 C2 1.379(2) . ? N1 C9 1.388(2) . ? N1 C10 1.422(2) . ? C2 N3 1.304(2) . ? C2 C16 1.486(3) . ? N3 C4 1.390(3) . ? C4 C5 1.395(3) . ? C4 C9 1.398(3) . ? C5 C6 1.376(3) . ? C6 C7 1.395(3) . ? C7 C8 1.385(3) . ? C8 C9 1.385(3) . ? C10 C11 1.382(3) . ? C10 C15 1.391(2) . ? C11 C12 1.380(3) . ? C12 C13 1.384(3) . ? C13 C14 1.377(3) . ? C14 C15 1.374(3) . ? C15 N15 1.464(2) . ? N15 O15A 1.219(2) . ? N15 O15B 1.221(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 C2 N1 C9 106.54(15) . . ? C2 N1 C10 127.53(15) . . ? C9 N1 C10 125.54(14) . . ? N3 C2 N1 113.03(17) . . ? N3 C2 C16 124.56(17) . . ? N1 C2 C16 122.39(17) . . ? C2 N3 C4 105.20(15) . . ? N3 C4 C5 130.05(18) . . ? N3 C4 C9 110.27(16) . . ? C5 C4 C9 119.68(19) . . ? C6 C5 C4 117.6(2) . . ? C5 C6 C7 121.88(19) . . ? C8 C7 C6 121.5(2) . . ? C9 C8 C7 116.15(19) . . ? C8 C9 N1 131.92(17) . . ? C8 C9 C4 123.11(17) . . ? N1 C9 C4 104.97(16) . . ? C11 C10 C15 117.85(16) . . ? C11 C10 N1 120.49(16) . . ? C15 C10 N1 121.65(16) . . ? C12 C11 C10 120.36(18) . . ? C11 C12 C13 120.67(18) . . ? C14 C13 C12 119.80(18) . . ? C15 C14 C13 118.94(18) . . ? C14 C15 C10 122.35(17) . . ? C14 C15 N15 117.73(16) . . ? C10 C15 N15 119.91(16) . . ? O15A N15 O15B 124.80(19) . . ? O15A N15 C15 118.09(18) . . ? O15B N15 C15 117.11(19) . . ? _diffrn_measured_fraction_theta_max 0.979 _diffrn_reflns_theta_full 26.39 _diffrn_measured_fraction_theta_full 0.979 _refine_diff_density_max 0.249 _refine_diff_density_min -0.235 _refine_diff_density_rms 0.042 data_7 _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point 404 _chemical_formula_moiety 'C13 H9 N3 O2' _chemical_formula_sum 'C13 H9 N3 O2' _chemical_formula_weight 239.23 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) loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z' _cell_length_a 7.519(5) _cell_length_b 7.223(5) _cell_length_c 10.049(7) _cell_angle_alpha 90.00 _cell_angle_beta 103.631(11) _cell_angle_gamma 90.00 _cell_volume 530.4(6) _cell_formula_units_Z 2 _cell_measurement_temperature 150(2) _cell_measurement_reflns_used 1004 _cell_measurement_theta_min 3 _cell_measurement_theta_max 28.5 _exptl_crystal_description tablet _exptl_crystal_colour colourless _exptl_crystal_size_max 0.45 _exptl_crystal_size_mid 0.36 _exptl_crystal_size_min 0.15 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.498 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 248 _exptl_absorpt_coefficient_mu 0.105 _exptl_absorpt_correction_type multiscan _exptl_absorpt_correction_T_min 0.345 _exptl_absorpt_correction_T_max 0.928 _exptl_absorpt_process_details sadabs _exptl_special_details ; ? ; _diffrn_ambient_temperature 150(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 'CCD area detector' _diffrn_measurement_method 'phi and omega scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 1938 _diffrn_reflns_av_R_equivalents 0.0403 _diffrn_reflns_av_sigmaI/netI 0.0758 _diffrn_reflns_limit_h_min -7 _diffrn_reflns_limit_h_max 10 _diffrn_reflns_limit_k_min -9 _diffrn_reflns_limit_k_max 4 _diffrn_reflns_limit_l_min -13 _diffrn_reflns_limit_l_max 8 _diffrn_reflns_theta_min 2.09 _diffrn_reflns_theta_max 28.91 _reflns_number_total 1412 _reflns_number_gt 1078 _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 ; The origin was fixed along the direction of the polar axis by applying a shift-limiting restraint the weighted sum of the coordinates. ; _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^)+(0.0589P)^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_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _refine_ls_abs_structure_Flack -2(3) _refine_ls_number_reflns 1412 _refine_ls_number_parameters 163 _refine_ls_number_restraints 1 _refine_ls_R_factor_all 0.0618 _refine_ls_R_factor_gt 0.0502 _refine_ls_wR_factor_ref 0.1192 _refine_ls_wR_factor_gt 0.1148 _refine_ls_goodness_of_fit_ref 0.930 _refine_ls_restrained_S_all 0.930 _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 N111 N 0.5561(5) 0.3452(5) 0.0700(4) 0.0306(10) Uani 1 1 d . . . C14 C 0.6471(6) 0.3789(6) -0.1440(4) 0.0259(10) Uani 1 1 d . . . H14 H 0.5301 0.3328 -0.1889 0.031 Uiso 1 1 calc R . . N1 N 0.8926(4) 0.5246(5) 0.2040(3) 0.0259(8) Uani 1 1 d . . . C12 C 0.9439(6) 0.4910(6) -0.1501(4) 0.0272(10) Uani 1 1 d . . . H12 H 1.0331 0.5168 -0.2006 0.033 Uiso 1 1 calc R . . O111 O 0.3961(5) 0.3895(6) 0.0207(3) 0.0476(10) Uani 1 1 d . . . C10 C 0.8559(5) 0.4820(5) 0.0633(4) 0.0226(9) Uani 1 1 d . . . C4 C 1.0244(5) 0.6117(5) 0.4146(4) 0.0235(10) Uani 1 1 d . . . O112 O 0.6062(4) 0.2534(5) 0.1710(3) 0.0386(9) Uani 1 1 d . . . C11 C 0.9844(6) 0.5260(6) -0.0111(4) 0.0286(10) Uani 1 1 d . . . H11 H 1.0985 0.5794 0.0331 0.034 Uiso 1 1 calc R . . C3 C 0.8372(6) 0.6574(6) 0.3820(4) 0.0259(10) Uani 1 1 d . . . H3 H 0.7762 0.7155 0.4435 0.031 Uiso 1 1 calc R . . N2 N 0.7573(5) 0.6096(5) 0.2556(4) 0.0290(9) Uani 1 1 d . . . C15 C 0.6929(5) 0.4075(6) -0.0048(4) 0.0247(10) Uani 1 1 d . . . C7 C 1.3672(6) 0.4869(6) 0.4062(4) 0.0283(10) Uani 1 1 d . . . H7 H 1.4868 0.4452 0.4054 0.034 Uiso 1 1 calc R . . C9 C 1.0553(5) 0.5240(6) 0.2991(4) 0.0221(9) Uani 1 1 d . . . C8 C 1.2265(6) 0.4555(5) 0.2934(4) 0.0244(10) Uani 1 1 d . . . H8 H 1.2451 0.3905 0.2157 0.029 Uiso 1 1 calc R . . C5 C 1.1685(6) 0.6399(6) 0.5277(4) 0.0262(10) Uani 1 1 d . . . H5 H 1.1495 0.7003 0.6072 0.031 Uiso 1 1 calc R . . C6 C 1.3391(6) 0.5784(6) 0.5218(4) 0.0289(10) Uani 1 1 d . . . H6 H 1.4397 0.5984 0.5976 0.035 Uiso 1 1 calc R . . C13 C 0.7782(6) 0.4200(6) -0.2167(4) 0.0283(11) Uani 1 1 d . . . H13 H 0.7526 0.3987 -0.3127 0.034 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 N111 0.032(2) 0.035(2) 0.026(2) -0.0059(18) 0.010(2) -0.0025(18) C14 0.018(2) 0.030(2) 0.027(2) -0.003(2) -0.001(2) 0.0012(19) N1 0.0173(18) 0.036(2) 0.0234(18) -0.0038(16) 0.0026(18) -0.0007(16) C12 0.026(2) 0.028(2) 0.029(2) 0.004(2) 0.010(2) 0.0011(19) O111 0.0254(18) 0.076(3) 0.044(2) -0.0016(19) 0.0114(19) 0.0031(18) C10 0.017(2) 0.022(2) 0.027(2) -0.0026(18) 0.001(2) 0.0004(17) C4 0.022(2) 0.024(2) 0.024(2) 0.0012(19) 0.004(2) -0.0017(19) O112 0.040(2) 0.043(2) 0.0325(18) 0.0063(16) 0.0085(18) -0.0113(17) C11 0.024(2) 0.026(2) 0.034(2) 0.003(2) 0.004(2) -0.0017(19) C3 0.024(2) 0.027(2) 0.028(2) -0.005(2) 0.010(2) -0.0004(18) N2 0.0215(19) 0.031(2) 0.035(2) -0.0077(17) 0.0078(19) 0.0016(16) C15 0.021(2) 0.026(2) 0.026(2) 0.0006(19) 0.006(2) 0.0021(18) C7 0.019(2) 0.031(2) 0.034(2) 0.003(2) 0.003(2) -0.0012(19) C9 0.021(2) 0.025(2) 0.019(2) 0.0021(18) 0.001(2) -0.0011(18) C8 0.023(2) 0.025(2) 0.025(2) -0.0003(18) 0.006(2) -0.0004(17) C5 0.029(2) 0.026(2) 0.021(2) -0.0024(19) 0.001(2) -0.0001(19) C6 0.025(2) 0.029(2) 0.028(2) 0.0039(19) -0.003(2) -0.0025(18) C13 0.032(3) 0.032(2) 0.020(2) -0.0041(19) 0.005(2) 0.008(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 N111 O112 1.196(5) . ? N111 O111 1.231(5) . ? N111 C15 1.480(4) . ? C14 C15 1.375(5) . ? C14 C13 1.390(5) . ? N1 C9 1.363(5) . ? N1 N2 1.389(4) . ? N1 C10 1.409(5) . ? C12 C13 1.368(6) . ? C12 C11 1.382(6) . ? C10 C15 1.366(6) . ? C10 C11 1.391(5) . ? C4 C5 1.389(6) . ? C4 C9 1.389(5) . ? C4 C3 1.407(6) . ? C3 N2 1.317(5) . ? C7 C8 1.375(6) . ? C7 C6 1.395(5) . ? C9 C8 1.392(5) . ? C5 C6 1.372(6) . ? 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 O112 N111 O111 124.6(3) . . ? O112 N111 C15 118.8(4) . . ? O111 N111 C15 116.6(4) . . ? C15 C14 C13 117.7(4) . . ? C9 N1 N2 110.8(3) . . ? C9 N1 C10 129.3(3) . . ? N2 N1 C10 118.9(3) . . ? C13 C12 C11 121.5(3) . . ? C15 C10 C11 118.4(4) . . ? C15 C10 N1 122.0(3) . . ? C11 C10 N1 119.5(4) . . ? C5 C4 C9 119.9(3) . . ? C5 C4 C3 134.5(3) . . ? C9 C4 C3 105.6(4) . . ? C12 C11 C10 119.1(4) . . ? N2 C3 C4 111.5(3) . . ? C3 N2 N1 105.5(3) . . ? C10 C15 C14 123.3(3) . . ? C10 C15 N111 120.9(3) . . ? C14 C15 N111 115.7(4) . . ? C8 C7 C6 121.7(4) . . ? N1 C9 C4 106.5(3) . . ? N1 C9 C8 131.2(3) . . ? C4 C9 C8 122.3(4) . . ? C7 C8 C9 116.6(3) . . ? C6 C5 C4 118.3(4) . . ? C5 C6 C7 121.1(5) . . ? C12 C13 C14 120.0(4) . . ? _diffrn_measured_fraction_theta_max 0.794 _diffrn_reflns_theta_full 28.91 _diffrn_measured_fraction_theta_full 0.794 _refine_diff_density_max 0.276 _refine_diff_density_min -0.245 _refine_diff_density_rms 0.057