data_in-105 _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C16H13NO2' _chemical_formula_weight 251.27 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 ? _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 9.7368(5) _cell_length_b 9.5514(4) _cell_length_c 13.8091(7) _cell_angle_alpha 90.00 _cell_angle_beta 107.501(5) _cell_angle_gamma 90.00 _cell_volume 1224.80(11) _cell_formula_units_Z 4 _cell_measurement_temperature 120(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description ? _exptl_crystal_colour ? _exptl_crystal_size_max ? _exptl_crystal_size_mid ? _exptl_crystal_size_min ? _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.363 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 528 _exptl_absorpt_coefficient_mu 0.090 _exptl_absorpt_correction_type ? _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 120(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 ? _diffrn_measurement_method ? _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 7887 _diffrn_reflns_av_R_equivalents 0.0325 _diffrn_reflns_av_sigmaI/netI 0.0247 _diffrn_reflns_limit_h_min -11 _diffrn_reflns_limit_h_max 11 _diffrn_reflns_limit_k_min -11 _diffrn_reflns_limit_k_max 10 _diffrn_reflns_limit_l_min -16 _diffrn_reflns_limit_l_max 15 _diffrn_reflns_theta_min 3.06 _diffrn_reflns_theta_max 25.00 _reflns_number_total 2159 _reflns_number_gt 1726 _reflns_threshold_expression >2sigma(I) _computing_data_collection ? _computing_cell_refinement ? _computing_data_reduction ? _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics ? _computing_publication_material ? _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^)+(0.0700P)^2^+0.2000P] 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 2156 _refine_ls_number_parameters 173 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0500 _refine_ls_R_factor_gt 0.0398 _refine_ls_wR_factor_ref 0.1197 _refine_ls_wR_factor_gt 0.1154 _refine_ls_goodness_of_fit_ref 1.103 _refine_ls_restrained_S_all 1.103 _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_symetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group O1 O 0.85874(12) 0.65641(12) 0.23103(9) 0.0310(3) Uani 1 1 d . . . C1 C 0.94603(16) 0.47421(15) 0.14799(11) 0.0203(4) Uani 1 1 d . . . C2 C 0.83996(17) 0.57563(16) 0.15499(12) 0.0233(4) Uani 1 1 d . . . C3 C 0.70834(17) 0.58278(17) 0.07191(12) 0.0268(4) Uani 1 1 d . . . H3 H 0.6368 0.6491 0.0746 0.032 Uiso 1 1 calc R . . C4 C 0.68415(17) 0.49776(17) -0.00943(12) 0.0260(4) Uani 1 1 d . . . H4 H 0.5959 0.5062 -0.0625 0.031 Uiso 1 1 calc R . . C5 C 0.78651(17) 0.39525(16) -0.01873(11) 0.0228(4) Uani 1 1 d . . . C6 C 0.75717(18) 0.30779(17) -0.10483(12) 0.0269(4) Uani 1 1 d . . . H6 H 0.6683 0.3172 -0.1571 0.032 Uiso 1 1 calc R . . C7 C 0.85480(19) 0.20937(18) -0.11431(13) 0.0305(4) Uani 1 1 d . . . H7 H 0.8342 0.1508 -0.1725 0.037 Uiso 1 1 calc R . . C8 C 0.98464(18) 0.19663(17) -0.03721(12) 0.0281(4) Uani 1 1 d . . . H8 H 1.0527 0.1285 -0.0432 0.034 Uiso 1 1 calc R . . C9 C 1.01617(17) 0.28081(17) 0.04742(12) 0.0236(4) Uani 1 1 d . . . H9 H 1.1058 0.2698 0.0987 0.028 Uiso 1 1 calc R . . C10 C 0.91859(16) 0.38292(16) 0.05989(11) 0.0202(4) Uani 1 1 d . . . C11 C 1.07522(17) 0.46479(16) 0.22700(11) 0.0214(4) Uani 1 1 d . . . H11 H 1.1428 0.3960 0.2213 0.026 Uiso 1 1 calc R . . N12 N 1.10994(14) 0.54380(14) 0.30828(10) 0.0233(3) Uani 1 1 d . . . H12 H 1.0489 0.6092 0.3135 0.028 Uiso 1 1 calc R . . C13 C 1.24503(18) 0.52928(19) 0.39111(12) 0.0271(4) Uani 1 1 d . . . H13A H 1.2568(2) 0.4326(13) 0.4116(3) 0.033 Uiso 1 1 calc R . . H13B H 1.2378(2) 0.5831(7) 0.4483(8) 0.033 Uiso 1 1 calc R . . C14 C 1.37523(17) 0.57513(17) 0.36515(11) 0.0250(4) Uani 1 1 d . . . O15 O 1.44225(17) 0.48315(15) 0.32060(11) 0.0520(4) Uani 1 1 d . . . C16 C 1.5597(2) 0.5561(3) 0.30719(17) 0.0502(6) Uani 1 1 d . . . H16 H 1.6300 0.5170 0.2800 0.060 Uiso 1 1 calc R . . C17 C 1.5591(2) 0.6858(2) 0.33740(14) 0.0442(5) Uani 1 1 d . . . H17 H 1.6264 0.7569 0.3353 0.053 Uiso 1 1 calc R . . C18 C 1.4386(2) 0.69975(18) 0.37371(14) 0.0345(4) Uani 1 1 d . . . H18 H 1.4086 0.7827 0.3994 0.041 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 O1 0.0291(7) 0.0313(7) 0.0321(7) -0.0105(5) 0.0085(5) 0.0013(5) C1 0.0210(8) 0.0206(8) 0.0205(8) 0.0026(6) 0.0081(7) -0.0025(6) C2 0.0236(9) 0.0227(8) 0.0252(8) 0.0003(7) 0.0097(7) -0.0028(7) C3 0.0223(9) 0.0250(9) 0.0331(9) 0.0016(7) 0.0082(7) 0.0025(7) C4 0.0200(9) 0.0282(9) 0.0268(9) 0.0043(7) 0.0025(7) -0.0017(7) C5 0.0235(8) 0.0244(8) 0.0212(8) 0.0032(6) 0.0080(7) -0.0042(7) C6 0.0269(9) 0.0322(9) 0.0204(8) 0.0002(7) 0.0053(7) -0.0065(7) C7 0.0367(10) 0.0339(10) 0.0239(9) -0.0073(7) 0.0138(8) -0.0088(8) C8 0.0319(10) 0.0279(9) 0.0296(9) -0.0017(7) 0.0172(8) -0.0006(7) C9 0.0234(9) 0.0271(9) 0.0220(8) 0.0026(7) 0.0094(7) -0.0007(7) C10 0.0224(8) 0.0208(8) 0.0190(8) 0.0037(6) 0.0090(6) -0.0038(6) C11 0.0237(9) 0.0215(8) 0.0210(8) 0.0038(6) 0.0100(7) -0.0002(6) N12 0.0234(8) 0.0260(7) 0.0213(7) -0.0003(6) 0.0079(6) -0.0001(6) C13 0.0238(9) 0.0360(10) 0.0200(8) 0.0010(7) 0.0042(7) -0.0017(7) C14 0.0242(9) 0.0320(9) 0.0171(8) -0.0016(7) 0.0037(7) 0.0019(7) O15 0.0645(10) 0.0416(8) 0.0631(10) -0.0003(7) 0.0393(8) 0.0063(7) C16 0.0383(12) 0.0704(16) 0.0532(13) 0.0196(12) 0.0307(10) 0.0199(11) C17 0.0324(11) 0.0620(14) 0.0383(11) -0.0034(10) 0.0109(9) -0.0201(10) C18 0.0370(10) 0.0265(9) 0.0471(11) -0.0106(8) 0.0235(9) -0.0089(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 C2 1.2712(18) . ? C1 C11 1.398(2) . ? C1 C2 1.440(2) . ? C1 C10 1.455(2) . ? C2 C3 1.442(2) . ? C3 C4 1.348(2) . ? C4 C5 1.430(2) . ? C5 C6 1.410(2) . ? C5 C10 1.417(2) . ? C6 C7 1.371(2) . ? C7 C8 1.392(2) . ? C8 C9 1.375(2) . ? C9 C10 1.408(2) . ? C11 N12 1.3098(19) . ? N12 C13 1.467(2) . ? C13 C14 1.483(2) . ? C14 C18 1.330(2) . ? C14 O15 1.348(2) . ? O15 C16 1.398(2) . ? C16 C17 1.308(3) . ? C17 C18 1.413(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 C11 C1 C2 119.07(14) . . ? C11 C1 C10 120.65(14) . . ? C2 C1 C10 120.28(14) . . ? O1 C2 C1 122.39(14) . . ? O1 C2 C3 120.08(14) . . ? C1 C2 C3 117.53(14) . . ? C4 C3 C2 121.68(15) . . ? C3 C4 C5 122.37(15) . . ? C6 C5 C10 120.26(14) . . ? C6 C5 C4 120.75(15) . . ? C10 C5 C4 118.99(14) . . ? C7 C6 C5 121.08(15) . . ? C6 C7 C8 118.90(15) . . ? C9 C8 C7 121.22(15) . . ? C8 C9 C10 121.51(15) . . ? C9 C10 C5 117.02(14) . . ? C9 C10 C1 123.82(14) . . ? C5 C10 C1 119.16(14) . . ? N12 C11 C1 124.84(14) . . ? C11 N12 C13 123.60(14) . . ? N12 C13 C14 114.50(13) . . ? C18 C14 O15 110.39(15) . . ? C18 C14 C13 130.58(15) . . ? O15 C14 C13 118.95(15) . . ? C14 O15 C16 105.25(15) . . ? C17 C16 O15 110.31(16) . . ? C16 C17 C18 106.64(17) . . ? C14 C18 C17 107.27(16) . . ? _diffrn_measured_fraction_theta_max 0.999 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 0.999 _refine_diff_density_max 0.345 _refine_diff_density_min -0.373 _refine_diff_density_rms 0.041