data_kjs11 _audit_creation_method SHELXTL _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C14 H16 N2 O' _chemical_formula_weight 228.29 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 9.1592(4) _cell_length_b 10.4770(4) _cell_length_c 12.3420(5) _cell_angle_alpha 90.00 _cell_angle_beta 90.8100(10) _cell_angle_gamma 90.00 _cell_volume 1184.23(8) _cell_formula_units_Z 4 _cell_measurement_temperature 163(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description plate _exptl_crystal_colour colorless _exptl_crystal_size_max 0.41 _exptl_crystal_size_mid 0.36 _exptl_crystal_size_min 0.27 _exptl_crystal_density_meas none _exptl_crystal_density_diffrn 1.280 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 488 _exptl_absorpt_coefficient_mu 0.082 _exptl_absorpt_correction_type none _exptl_absorpt_correction_T_min 0.9672 _exptl_absorpt_correction_T_max 0.9782 _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 163(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source '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 '50 frames' _diffrn_standards_interval_count 'initial 50 frames recollected' _diffrn_standards_interval_time ? _diffrn_standards_decay_% '< 1.0' _diffrn_reflns_number 12061 _diffrn_reflns_av_R_equivalents 0.0224 _diffrn_reflns_av_sigmaI/netI 0.0171 _diffrn_reflns_limit_h_min -12 _diffrn_reflns_limit_h_max 11 _diffrn_reflns_limit_k_min -13 _diffrn_reflns_limit_k_max 13 _diffrn_reflns_limit_l_min -16 _diffrn_reflns_limit_l_max 15 _diffrn_reflns_theta_min 2.22 _diffrn_reflns_theta_max 28.27 _reflns_number_total 2851 _reflns_number_gt 2510 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SMART/SAINT' _computing_data_reduction 'Bruker SHELXTL' _computing_structure_solution 'Bruker SHELXTL' _computing_structure_refinement 'Bruker SHELXTL' _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^)+(0.0412P)^2^+0.3636P] 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 refall _refine_ls_extinction_method SHELXTL _refine_ls_extinction_coef 0.011(2) _refine_ls_extinction_expression 'Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^' _refine_ls_number_reflns 2851 _refine_ls_number_parameters 219 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0401 _refine_ls_R_factor_gt 0.0347 _refine_ls_wR_factor_ref 0.0905 _refine_ls_wR_factor_gt 0.0861 _refine_ls_goodness_of_fit_ref 1.023 _refine_ls_restrained_S_all 1.023 _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 0.40641(8) 0.94739(7) 0.22391(6) 0.03027(19) Uani 1 1 d . . . N1 N 0.58092(9) 0.80063(8) 0.18230(6) 0.02155(19) Uani 1 1 d . . . C2 C 0.43783(11) 0.83726(9) 0.20355(7) 0.0217(2) Uani 1 1 d . . . C3 C 0.32228(12) 0.73239(10) 0.20004(8) 0.0255(2) Uani 1 1 d . . . C4 C 0.25909(12) 0.71275(10) 0.08440(9) 0.0279(2) Uani 1 1 d . . . C5 C 0.36403(14) 0.65399(11) 0.00133(9) 0.0326(3) Uani 1 1 d . . . C6 C 0.51030(12) 0.71686(10) 0.01364(8) 0.0272(2) Uani 1 1 d . . . C7 C 0.55304(12) 0.82524(10) -0.03292(8) 0.0274(2) Uani 1 1 d . . . C8 C 0.67975(12) 0.89528(10) 0.01790(8) 0.0263(2) Uani 1 1 d . . . N9 N 0.66803(9) 0.90034(8) 0.13955(7) 0.02210(19) Uani 1 1 d . . . C10 C 0.59488(12) 0.68402(10) 0.11528(9) 0.0270(2) Uani 1 1 d . . . C11 C 0.79862(10) 0.92085(9) 0.19916(8) 0.0229(2) Uani 1 1 d . . . C12 C 0.91158(12) 0.99372(11) 0.15520(10) 0.0320(2) Uani 1 1 d . . . C13 C 1.03693(13) 1.01917(12) 0.21619(11) 0.0372(3) Uani 1 1 d . . . C14 C 1.05289(12) 0.97299(11) 0.32054(11) 0.0355(3) Uani 1 1 d . . . C15 C 0.94115(13) 0.90168(11) 0.36468(10) 0.0335(3) Uani 1 1 d . . . C16 C 0.81452(12) 0.87577(10) 0.30531(9) 0.0272(2) Uani 1 1 d . . . H3A H 0.3618(15) 0.6515(13) 0.2296(11) 0.034(3) Uiso 1 1 d . . . H3B H 0.2429(14) 0.7611(13) 0.2459(11) 0.031(3) Uiso 1 1 d . . . H4A H 0.2234(14) 0.7988(13) 0.0574(11) 0.031(3) Uiso 1 1 d . . . H4B H 0.1715(15) 0.6577(14) 0.0896(11) 0.037(3) Uiso 1 1 d . . . H5A H 0.3717(16) 0.5593(14) 0.0162(12) 0.042(4) Uiso 1 1 d . . . H5B H 0.3211(16) 0.6661(14) -0.0722(13) 0.043(4) Uiso 1 1 d . . . H7 H 0.5003(15) 0.8665(13) -0.0922(11) 0.035(3) Uiso 1 1 d . . . H8A H 0.6852(13) 0.9833(12) -0.0098(10) 0.026(3) Uiso 1 1 d . . . H8B H 0.7747(15) 0.8514(13) 0.0002(11) 0.033(3) Uiso 1 1 d . . . H10A H 0.7005(15) 0.6724(12) 0.1019(10) 0.030(3) Uiso 1 1 d . . . H10B H 0.5589(14) 0.6104(13) 0.1537(11) 0.031(3) Uiso 1 1 d . . . H12 H 0.9011(15) 1.0287(14) 0.0831(12) 0.041(4) Uiso 1 1 d . . . H13 H 1.1142(17) 1.0694(15) 0.1848(13) 0.049(4) Uiso 1 1 d . . . H14 H 1.1417(17) 0.9894(14) 0.3628(12) 0.043(4) Uiso 1 1 d . . . H15 H 0.9508(17) 0.8694(15) 0.4381(13) 0.047(4) Uiso 1 1 d . . . H16 H 0.7370(14) 0.8264(13) 0.3361(11) 0.031(3) 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 0.0294(4) 0.0277(4) 0.0340(4) -0.0109(3) 0.0096(3) -0.0050(3) N1 0.0237(4) 0.0209(4) 0.0200(4) 0.0042(3) 0.0004(3) -0.0033(3) C2 0.0248(5) 0.0260(5) 0.0143(4) -0.0018(3) 0.0013(3) -0.0054(4) C3 0.0271(5) 0.0273(5) 0.0220(5) -0.0009(4) 0.0014(4) -0.0078(4) C4 0.0302(5) 0.0266(5) 0.0269(5) -0.0004(4) -0.0054(4) -0.0066(4) C5 0.0459(7) 0.0282(5) 0.0235(5) -0.0058(4) -0.0020(4) -0.0073(5) C6 0.0371(6) 0.0228(5) 0.0217(5) -0.0061(4) 0.0045(4) 0.0033(4) C7 0.0356(6) 0.0284(5) 0.0181(4) -0.0010(4) 0.0033(4) 0.0031(4) C8 0.0306(5) 0.0262(5) 0.0222(5) 0.0050(4) 0.0068(4) 0.0015(4) N9 0.0224(4) 0.0229(4) 0.0211(4) 0.0051(3) 0.0029(3) -0.0019(3) C10 0.0313(6) 0.0187(5) 0.0312(5) 0.0034(4) 0.0030(4) 0.0041(4) C11 0.0202(5) 0.0194(4) 0.0293(5) 0.0001(4) 0.0032(4) 0.0026(3) C12 0.0256(5) 0.0324(6) 0.0382(6) 0.0063(5) 0.0061(4) -0.0018(4) C13 0.0231(5) 0.0351(6) 0.0537(7) 0.0016(5) 0.0066(5) -0.0051(4) C14 0.0218(5) 0.0325(6) 0.0521(7) -0.0056(5) -0.0047(5) -0.0006(4) C15 0.0311(6) 0.0328(6) 0.0364(6) -0.0002(5) -0.0062(5) -0.0019(4) C16 0.0251(5) 0.0274(5) 0.0290(5) 0.0011(4) -0.0005(4) -0.0035(4) _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 1.2163(12) . ? N1 C2 1.3941(13) . ? N1 N9 1.4207(11) . ? N1 C10 1.4819(13) . ? C2 C3 1.5258(13) . ? C3 C4 1.5462(14) . ? C4 C5 1.5433(16) . ? C5 C6 1.4987(16) . ? C6 C7 1.3339(15) . ? C6 C10 1.5048(15) . ? C7 C8 1.5027(15) . ? C8 N9 1.5077(12) . ? N9 C11 1.4119(13) . ? C11 C16 1.3983(14) . ? C11 C12 1.4013(14) . ? C12 C13 1.3897(17) . ? C13 C14 1.3815(19) . ? C14 C15 1.3850(17) . ? C15 C16 1.3899(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 N9 113.69(8) . . ? C2 N1 C10 114.88(8) . . ? N9 N1 C10 110.22(8) . . ? O1 C2 N1 121.73(9) . . ? O1 C2 C3 121.53(9) . . ? N1 C2 C3 116.74(9) . . ? C2 C3 C4 111.87(8) . . ? C5 C4 C3 115.97(9) . . ? C6 C5 C4 108.75(8) . . ? C7 C6 C5 126.71(10) . . ? C7 C6 C10 113.77(10) . . ? C5 C6 C10 115.66(9) . . ? C6 C7 C8 117.75(10) . . ? C7 C8 N9 111.55(8) . . ? C11 N9 N1 113.23(7) . . ? C11 N9 C8 116.91(8) . . ? N1 N9 C8 113.09(8) . . ? N1 C10 C6 103.26(8) . . ? C16 C11 C12 118.63(10) . . ? C16 C11 N9 120.87(9) . . ? C12 C11 N9 120.39(9) . . ? C13 C12 C11 120.24(11) . . ? C14 C13 C12 120.89(11) . . ? C13 C14 C15 119.12(11) . . ? C14 C15 C16 120.91(11) . . ? C15 C16 C11 120.20(10) . . ? 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 N9 N1 C2 O1 -26.60(13) . . . . ? C10 N1 C2 O1 -154.89(9) . . . . ? N9 N1 C2 C3 153.40(8) . . . . ? C10 N1 C2 C3 25.11(12) . . . . ? O1 C2 C3 C4 92.58(12) . . . . ? N1 C2 C3 C4 -87.42(11) . . . . ? C2 C3 C4 C5 69.28(12) . . . . ? C3 C4 C5 C6 -43.72(13) . . . . ? C4 C5 C6 C7 -85.75(13) . . . . ? C4 C5 C6 C10 70.58(12) . . . . ? C5 C6 C7 C8 159.07(10) . . . . ? C10 C6 C7 C8 2.35(14) . . . . ? C6 C7 C8 N9 -43.65(13) . . . . ? C2 N1 N9 C11 125.89(9) . . . . ? C10 N1 N9 C11 -103.47(9) . . . . ? C2 N1 N9 C8 -98.18(9) . . . . ? C10 N1 N9 C8 32.46(11) . . . . ? C7 C8 N9 C11 158.03(9) . . . . ? C7 C8 N9 N1 23.82(11) . . . . ? C2 N1 C10 C6 57.32(10) . . . . ? N9 N1 C10 C6 -72.69(10) . . . . ? C7 C6 C10 N1 53.84(11) . . . . ? C5 C6 C10 N1 -105.58(10) . . . . ? N1 N9 C11 C16 -18.69(13) . . . . ? C8 N9 C11 C16 -152.84(9) . . . . ? N1 N9 C11 C12 165.24(9) . . . . ? C8 N9 C11 C12 31.09(13) . . . . ? C16 C11 C12 C13 0.56(16) . . . . ? N9 C11 C12 C13 176.72(10) . . . . ? C11 C12 C13 C14 0.28(18) . . . . ? C12 C13 C14 C15 -0.73(19) . . . . ? C13 C14 C15 C16 0.34(18) . . . . ? C14 C15 C16 C11 0.51(17) . . . . ? C12 C11 C16 C15 -0.95(16) . . . . ? N9 C11 C16 C15 -177.09(10) . . . . ? _diffrn_measured_fraction_theta_max 0.970 _diffrn_reflns_theta_full 28.27 _diffrn_measured_fraction_theta_full 0.970 _refine_diff_density_max 0.261 _refine_diff_density_min -0.157 _refine_diff_density_rms 0.034