data_s24um _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C16 H10 N O2' _chemical_formula_weight 248.25 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 11.101(6) _cell_length_b 7.937(4) _cell_length_c 14.958(8) _cell_angle_alpha 90.00 _cell_angle_beta 90.927(9) _cell_angle_gamma 90.00 _cell_volume 1317.8(13) _cell_formula_units_Z 4 _cell_measurement_temperature 153(2) _cell_measurement_reflns_used 2776 _cell_measurement_theta_min 27.75 _cell_measurement_theta_max 2.27 _exptl_crystal_description plate _exptl_crystal_colour colorless _exptl_crystal_size_max 0.441 _exptl_crystal_size_mid 0.204 _exptl_crystal_size_min 0.048 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.251 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 516 _exptl_absorpt_coefficient_mu 0.083 _exptl_absorpt_correction_type none _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 153(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 'omega scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 10907 _diffrn_reflns_av_R_equivalents 0.1836 _diffrn_reflns_av_sigmaI/netI 0.1457 _diffrn_reflns_limit_h_min -14 _diffrn_reflns_limit_h_max 14 _diffrn_reflns_limit_k_min -10 _diffrn_reflns_limit_k_max 10 _diffrn_reflns_limit_l_min -19 _diffrn_reflns_limit_l_max 19 _diffrn_reflns_theta_min 2.27 _diffrn_reflns_theta_max 28.82 _reflns_number_total 3164 _reflns_number_gt 1803 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SMART' _computing_data_reduction 'Bruker SAINT' _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^)+(0.0874P)^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 mixed _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 3164 _refine_ls_number_parameters 245 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.1488 _refine_ls_R_factor_gt 0.0826 _refine_ls_wR_factor_ref 0.1955 _refine_ls_wR_factor_gt 0.1707 _refine_ls_goodness_of_fit_ref 0.969 _refine_ls_restrained_S_all 0.969 _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 H19 H 0.317(2) 0.392(3) 0.3636(17) 0.017(7) Uiso 1 1 d . . . H13 H -0.120(4) 0.000(5) 0.307(3) 0.067(12) Uiso 1 1 d . . . H15 H 0.177(3) -0.080(4) 0.458(2) 0.035(8) Uiso 1 1 d . . . H9 H 0.338(3) 0.195(4) 0.5795(17) 0.025(7) Uiso 1 1 d . . . H7 H 0.116(3) 0.531(4) 0.693(2) 0.036(8) Uiso 1 1 d . . . H6 H 0.097(3) 0.666(4) 0.561(2) 0.041(9) Uiso 1 1 d . . . H161 H 0.443(3) -0.005(4) 0.304(2) 0.044(9) Uiso 1 1 d . . . H12 H -0.006(3) 0.183(4) 0.219(2) 0.051(10) Uiso 1 1 d . . . H8 H 0.244(3) 0.293(4) 0.704(2) 0.031(8) Uiso 1 1 d . . . H5 H 0.193(3) 0.576(4) 0.436(2) 0.044(9) Uiso 1 1 d . . . H2 H 0.508(3) 0.451(4) 0.4060(18) 0.033(8) Uiso 1 1 d . . . H1 H 0.588(3) 0.249(3) 0.3077(19) 0.026(7) Uiso 1 1 d . . . H14 H -0.022(3) -0.137(4) 0.422(2) 0.037(9) Uiso 1 1 d . . . H3 H 0.346(2) 0.067(3) 0.4350(17) 0.019(7) Uiso 1 1 d . . . H162 H 0.392(2) 0.165(3) 0.2584(18) 0.021(7) Uiso 1 1 d . . . H11 H 0.185(2) 0.248(3) 0.2502(17) 0.017(7) Uiso 1 1 d . . . O1 O 0.59104(19) 0.1271(2) 0.42195(12) 0.0340(5) Uani 1 1 d . . . C4 C 0.2770(3) 0.3780(3) 0.49348(18) 0.0255(6) Uani 1 1 d . . . C10 C 0.1997(3) 0.0921(3) 0.35817(18) 0.0268(7) Uani 1 1 d . . . C19 C 0.3422(3) 0.3223(3) 0.41205(18) 0.0261(6) Uani 1 1 d . . . C16 C 0.4219(3) 0.1141(4) 0.3137(2) 0.0315(7) Uani 1 1 d . . . C3 C 0.3267(3) 0.1377(3) 0.38450(17) 0.0270(7) Uani 1 1 d . . . C2 C 0.4794(3) 0.3432(3) 0.41376(18) 0.0276(7) Uani 1 1 d . . . C9 C 0.2896(3) 0.2934(4) 0.57422(18) 0.0282(7) Uani 1 1 d . . . C15 C 0.1370(3) -0.0230(4) 0.40805(19) 0.0321(7) Uani 1 1 d . . . C12 C 0.0235(3) 0.1292(4) 0.2669(2) 0.0340(8) Uani 1 1 d . . . C11 C 0.1421(3) 0.1661(4) 0.28545(18) 0.0308(7) Uani 1 1 d . . . C8 C 0.2328(3) 0.3516(4) 0.6490(2) 0.0335(7) Uani 1 1 d . . . C5 C 0.2031(3) 0.5171(4) 0.4904(2) 0.0330(7) Uani 1 1 d . . . C13 C -0.0387(3) 0.0177(4) 0.3175(2) 0.0340(7) Uani 1 1 d . . . C7 C 0.1613(3) 0.4927(4) 0.6453(2) 0.0392(8) Uani 1 1 d . . . C6 C 0.1462(3) 0.5742(4) 0.5655(2) 0.0394(8) Uani 1 1 d . . . C14 C 0.0184(3) -0.0606(4) 0.3881(2) 0.0367(8) Uani 1 1 d . . . C1 C 0.5277(3) 0.2139(3) 0.34758(19) 0.0304(7) Uani 1 1 d . . . O2 O 0.57172(18) 0.2446(2) 0.55929(13) 0.0328(5) Uani 1 1 d . . . C17 C 0.5502(3) 0.2426(3) 0.4817(2) 0.0278(6) 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 0.0352(13) 0.0316(11) 0.0351(12) -0.0011(9) -0.0062(9) 0.0050(9) C4 0.0268(16) 0.0222(13) 0.0273(14) -0.0017(11) -0.0065(12) -0.0058(12) C10 0.0349(17) 0.0206(13) 0.0245(14) -0.0042(11) -0.0070(12) 0.0012(12) C19 0.0339(18) 0.0211(13) 0.0230(14) 0.0024(11) -0.0061(12) 0.0013(12) C16 0.0398(19) 0.0279(15) 0.0268(16) -0.0040(12) -0.0039(13) 0.0030(14) C3 0.0376(18) 0.0247(14) 0.0184(13) 0.0012(11) -0.0059(12) -0.0029(12) C2 0.0356(18) 0.0190(13) 0.0282(14) 0.0010(11) -0.0026(12) -0.0025(12) C9 0.0266(17) 0.0305(15) 0.0274(15) -0.0022(12) -0.0056(12) -0.0022(13) C15 0.0415(19) 0.0304(16) 0.0242(15) 0.0024(12) -0.0084(13) -0.0017(14) C12 0.043(2) 0.0326(16) 0.0262(15) -0.0037(13) -0.0149(14) 0.0003(14) C11 0.0412(19) 0.0270(15) 0.0239(14) 0.0003(12) -0.0048(13) -0.0025(14) C8 0.0363(18) 0.0390(17) 0.0252(15) -0.0010(13) -0.0041(13) -0.0069(15) C5 0.0403(19) 0.0266(15) 0.0319(16) 0.0008(12) -0.0044(14) 0.0016(14) C13 0.0320(19) 0.0364(17) 0.0335(16) -0.0091(13) -0.0083(14) -0.0009(14) C7 0.040(2) 0.0401(18) 0.0379(18) -0.0121(14) 0.0118(15) -0.0083(16) C6 0.045(2) 0.0283(16) 0.0451(19) -0.0014(14) 0.0021(16) 0.0056(15) C14 0.042(2) 0.0390(17) 0.0293(16) 0.0003(14) -0.0043(14) -0.0094(15) C1 0.0365(19) 0.0283(15) 0.0264(15) 0.0028(12) -0.0002(13) 0.0036(13) O2 0.0378(13) 0.0319(11) 0.0285(12) 0.0028(9) -0.0090(9) 0.0002(9) C17 0.0217(16) 0.0249(14) 0.0369(17) 0.0017(12) 0.0001(12) -0.0024(12) _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 C17 1.363(3) . ? O1 C1 1.477(3) . ? C4 C5 1.376(4) . ? C4 C9 1.387(4) . ? C4 C19 1.494(4) . ? C10 C15 1.376(4) . ? C10 C11 1.383(4) . ? C10 C3 1.503(4) . ? C19 C3 1.531(4) . ? C19 C2 1.531(4) . ? C16 C1 1.498(4) . ? C16 C3 1.520(4) . ? C2 C17 1.504(4) . ? C2 C1 1.529(4) . ? C9 C8 1.373(4) . ? C15 C14 1.378(4) . ? C12 C13 1.360(4) . ? C12 C11 1.373(4) . ? C8 C7 1.373(5) . ? C5 C6 1.374(4) . ? C13 C14 1.372(4) . ? C7 C6 1.366(5) . ? O2 C17 1.181(3) . ? 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 C17 O1 C1 91.2(2) . . ? C5 C4 C9 118.0(3) . . ? C5 C4 C19 120.5(3) . . ? C9 C4 C19 121.6(3) . . ? C15 C10 C11 118.5(3) . . ? C15 C10 C3 119.9(2) . . ? C11 C10 C3 121.6(3) . . ? C4 C19 C3 116.7(2) . . ? C4 C19 C2 116.7(2) . . ? C3 C19 C2 102.5(2) . . ? C1 C16 C3 104.4(2) . . ? C10 C3 C16 116.6(2) . . ? C10 C3 C19 113.7(2) . . ? C16 C3 C19 103.2(2) . . ? C17 C2 C1 84.0(2) . . ? C17 C2 C19 117.5(2) . . ? C1 C2 C19 106.0(2) . . ? C8 C9 C4 120.4(3) . . ? C10 C15 C14 121.1(3) . . ? C13 C12 C11 121.3(3) . . ? C12 C11 C10 119.9(3) . . ? C7 C8 C9 120.9(3) . . ? C6 C5 C4 121.3(3) . . ? C12 C13 C14 119.4(3) . . ? C6 C7 C8 119.0(3) . . ? C7 C6 C5 120.4(3) . . ? C13 C14 C15 119.8(3) . . ? O1 C1 C16 111.7(2) . . ? O1 C1 C2 89.6(2) . . ? C16 C1 C2 107.0(3) . . ? O2 C17 O1 126.1(3) . . ? O2 C17 C2 138.8(3) . . ? O1 C17 C2 95.2(2) . . ? _diffrn_measured_fraction_theta_max 0.920 _diffrn_reflns_theta_full 28.82 _diffrn_measured_fraction_theta_full 0.920 _refine_diff_density_max 0.316 _refine_diff_density_min -0.313 _refine_diff_density_rms 0.069