data_kjs15 _audit_creation_method SHELXTL _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C15 H18 N2 O' _chemical_formula_weight 242.31 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 8.9659(8) _cell_length_b 13.1890(12) _cell_length_c 10.8474(10) _cell_angle_alpha 90.00 _cell_angle_beta 100.930(2) _cell_angle_gamma 90.00 _cell_volume 1259.4(2) _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 prism _exptl_crystal_colour colorless _exptl_crystal_size_max 0.48 _exptl_crystal_size_mid 0.42 _exptl_crystal_size_min 0.27 _exptl_crystal_density_meas n/a _exptl_crystal_density_diffrn 1.278 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 520 _exptl_absorpt_coefficient_mu 0.081 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.9621 _exptl_absorpt_correction_T_max 0.9784 _exptl_absorpt_process_details 'Bruker SADABS' _exptl_special_details ; ? ; _diffrn_ambient_temperature 163(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'normal-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'CCD area detector' _diffrn_measurement_method 'phi and 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 12777 _diffrn_reflns_av_R_equivalents 0.0242 _diffrn_reflns_av_sigmaI/netI 0.0172 _diffrn_reflns_limit_h_min -11 _diffrn_reflns_limit_h_max 11 _diffrn_reflns_limit_k_min -16 _diffrn_reflns_limit_k_max 16 _diffrn_reflns_limit_l_min -13 _diffrn_reflns_limit_l_max 13 _diffrn_reflns_theta_min 2.31 _diffrn_reflns_theta_max 27.10 _reflns_number_total 2775 _reflns_number_gt 2427 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SMART/SAINT' _computing_data_reduction 'Bruker SAINT' _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^)+(0.0447P)^2^+0.4509P] 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 none _refine_ls_extinction_coef ? _refine_ls_number_reflns 2775 _refine_ls_number_parameters 235 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0418 _refine_ls_R_factor_gt 0.0356 _refine_ls_wR_factor_ref 0.0949 _refine_ls_wR_factor_gt 0.0891 _refine_ls_goodness_of_fit_ref 1.035 _refine_ls_restrained_S_all 1.035 _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 0.96628(10) 0.23100(6) 0.96524(7) 0.0277(2) Uani 1 1 d . . . N1 N 0.70627(11) 0.15066(7) 0.84636(9) 0.0238(2) Uani 1 1 d . . . N2 N 0.81527(10) 0.18812(7) 0.77858(8) 0.0200(2) Uani 1 1 d . . . C1 C 0.95514(12) 0.21443(8) 0.85323(10) 0.0203(2) Uani 1 1 d . . . C2 C 1.08953(13) 0.22541(8) 0.78746(11) 0.0218(2) Uani 1 1 d . . . C3 C 1.18984(13) 0.12914(9) 0.78979(11) 0.0245(2) Uani 1 1 d . . . C4 C 1.14722(14) 0.05430(9) 0.68044(11) 0.0263(3) Uani 1 1 d . . . C5 C 1.02574(14) -0.02586(9) 0.69372(11) 0.0265(3) Uani 1 1 d . . . C6 C 0.89493(13) 0.02049(8) 0.74179(10) 0.0218(2) Uani 1 1 d . . . C7 C 0.85770(13) -0.00482(8) 0.85099(11) 0.0238(2) Uani 1 1 d . . . C8 C 0.74848(14) 0.05481(9) 0.91241(11) 0.0251(2) Uani 1 1 d . . . C9 C 0.82407(13) 0.11550(8) 0.67711(10) 0.0212(2) Uani 1 1 d . . . C10 C 0.61831(12) 0.22291(9) 0.89390(10) 0.0238(2) Uani 1 1 d . . . C11 C 0.54315(13) 0.19897(11) 0.99218(11) 0.0291(3) Uani 1 1 d . . . C12 C 0.44453(14) 0.26925(12) 1.03044(12) 0.0344(3) Uani 1 1 d . . . C13 C 0.41992(14) 0.36296(11) 0.97345(12) 0.0338(3) Uani 1 1 d . . . C14 C 0.49665(14) 0.38770(10) 0.87744(12) 0.0311(3) Uani 1 1 d . . . C15 C 0.59532(13) 0.31920(9) 0.83841(11) 0.0263(3) Uani 1 1 d . . . H2A H 1.0587(15) 0.2485(10) 0.7012(13) 0.024(3) Uiso 1 1 d . . . H2B H 1.1510(17) 0.2765(11) 0.8323(13) 0.029(4) Uiso 1 1 d . . . H3A H 1.2921(17) 0.1542(11) 0.7882(13) 0.029(3) Uiso 1 1 d . . . H3B H 1.1954(15) 0.0938(11) 0.8720(13) 0.027(3) Uiso 1 1 d . . . H4A H 1.1165(16) 0.0947(11) 0.6022(13) 0.029(3) Uiso 1 1 d . . . H4B H 1.2401(17) 0.0173(11) 0.6700(13) 0.032(4) Uiso 1 1 d . . . H5A H 1.0708(16) -0.0792(11) 0.7538(13) 0.029(3) Uiso 1 1 d . . . H5B H 0.9931(16) -0.0581(11) 0.6109(14) 0.032(4) Uiso 1 1 d . . . H7A H 0.9060(16) -0.0609(11) 0.8998(13) 0.030(4) Uiso 1 1 d . . . H8A H 0.7947(16) 0.0661(11) 1.0041(13) 0.030(4) Uiso 1 1 d . . . H8B H 0.6519(17) 0.0164(11) 0.9100(13) 0.032(4) Uiso 1 1 d . . . H9A H 0.8853(15) 0.1450(10) 0.6192(12) 0.021(3) Uiso 1 1 d . . . H9B H 0.7189(16) 0.1052(10) 0.6304(13) 0.027(3) Uiso 1 1 d . . . H11 H 0.5572(16) 0.1331(12) 1.0307(14) 0.033(4) Uiso 1 1 d . . . H12 H 0.3932(18) 0.2510(12) 1.0976(15) 0.041(4) Uiso 1 1 d . . . H13 H 0.3502(19) 0.4119(12) 1.0020(15) 0.040(4) Uiso 1 1 d . . . H14 H 0.4788(18) 0.4570(13) 0.8376(15) 0.040(4) Uiso 1 1 d . . . H15 H 0.6480(16) 0.3338(11) 0.7717(14) 0.030(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 O1 0.0344(5) 0.0294(4) 0.0192(4) -0.0043(3) 0.0050(3) -0.0019(3) N1 0.0236(5) 0.0259(5) 0.0239(5) 0.0041(4) 0.0096(4) 0.0006(4) N2 0.0211(5) 0.0222(5) 0.0179(4) 0.0014(3) 0.0065(3) -0.0001(3) C1 0.0264(6) 0.0154(5) 0.0192(5) 0.0004(4) 0.0048(4) 0.0012(4) C2 0.0233(5) 0.0207(5) 0.0212(5) -0.0001(4) 0.0034(4) -0.0041(4) C3 0.0205(5) 0.0264(6) 0.0267(6) 0.0036(5) 0.0044(4) 0.0004(4) C4 0.0285(6) 0.0251(6) 0.0279(6) 0.0010(5) 0.0118(5) 0.0039(5) C5 0.0334(6) 0.0213(5) 0.0255(6) -0.0027(5) 0.0074(5) 0.0012(5) C6 0.0241(5) 0.0189(5) 0.0212(5) -0.0029(4) 0.0015(4) -0.0036(4) C7 0.0262(6) 0.0196(5) 0.0248(6) 0.0018(4) 0.0028(4) -0.0027(4) C8 0.0267(6) 0.0266(6) 0.0232(6) 0.0047(4) 0.0078(5) -0.0023(4) C9 0.0229(5) 0.0236(5) 0.0166(5) -0.0001(4) 0.0022(4) -0.0013(4) C10 0.0189(5) 0.0323(6) 0.0197(5) -0.0043(4) 0.0026(4) -0.0012(4) C11 0.0246(6) 0.0403(7) 0.0226(6) -0.0018(5) 0.0053(4) -0.0034(5) C12 0.0238(6) 0.0559(9) 0.0249(6) -0.0106(6) 0.0087(5) -0.0041(5) C13 0.0216(6) 0.0466(8) 0.0326(7) -0.0148(6) 0.0042(5) 0.0029(5) C14 0.0246(6) 0.0347(7) 0.0322(6) -0.0078(5) 0.0009(5) 0.0040(5) C15 0.0234(6) 0.0320(6) 0.0235(6) -0.0028(5) 0.0047(4) 0.0013(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 O1 C1 1.2198(13) . ? N1 C10 1.3965(14) . ? N1 N2 1.4185(12) . ? N1 C8 1.4669(15) . ? N2 C1 1.4013(14) . ? N2 C9 1.4725(14) . ? C1 C2 1.5191(15) . ? C2 C3 1.5534(16) . ? C3 C4 1.5348(17) . ? C4 C5 1.5441(17) . ? C5 C6 1.5010(16) . ? C6 C7 1.3327(16) . ? C6 C9 1.5156(15) . ? C7 C8 1.5062(16) . ? C10 C11 1.4010(16) . ? C10 C15 1.4038(17) . ? C11 C12 1.3973(18) . ? C12 C13 1.381(2) . ? C13 C14 1.3913(19) . ? C14 C15 1.3857(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 C10 N1 N2 116.52(9) . . ? C10 N1 C8 121.27(9) . . ? N2 N1 C8 114.46(9) . . ? C1 N2 N1 114.57(8) . . ? C1 N2 C9 115.09(8) . . ? N1 N2 C9 107.50(8) . . ? O1 C1 N2 121.01(10) . . ? O1 C1 C2 121.89(10) . . ? N2 C1 C2 117.05(9) . . ? C1 C2 C3 115.02(9) . . ? C4 C3 C2 117.03(10) . . ? C3 C4 C5 116.42(10) . . ? C6 C5 C4 111.41(9) . . ? C7 C6 C5 123.41(11) . . ? C7 C6 C9 117.71(10) . . ? C5 C6 C9 117.55(10) . . ? C6 C7 C8 123.76(10) . . ? N1 C8 C7 111.29(9) . . ? N2 C9 C6 105.60(8) . . ? N1 C10 C11 120.93(11) . . ? N1 C10 C15 120.41(10) . . ? C11 C10 C15 118.52(11) . . ? C12 C11 C10 119.95(13) . . ? C13 C12 C11 121.14(12) . . ? C12 C13 C14 119.03(12) . . ? C15 C14 C13 120.71(13) . . ? C14 C15 C10 120.61(12) . . ? 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 C10 N1 N2 C1 85.64(11) . . . . ? C8 N1 N2 C1 -64.17(12) . . . . ? C10 N1 N2 C9 -145.08(9) . . . . ? C8 N1 N2 C9 65.11(11) . . . . ? N1 N2 C1 O1 -19.72(14) . . . . ? C9 N2 C1 O1 -145.12(10) . . . . ? N1 N2 C1 C2 162.68(9) . . . . ? C9 N2 C1 C2 37.28(13) . . . . ? O1 C1 C2 C3 87.69(13) . . . . ? N2 C1 C2 C3 -94.74(12) . . . . ? C1 C2 C3 C4 90.43(12) . . . . ? C2 C3 C4 C5 -85.86(13) . . . . ? C3 C4 C5 C6 44.34(14) . . . . ? C4 C5 C6 C7 -117.05(12) . . . . ? C4 C5 C6 C9 49.43(13) . . . . ? C5 C6 C7 C8 167.17(10) . . . . ? C9 C6 C7 C8 0.71(16) . . . . ? C10 N1 C8 C7 -173.46(10) . . . . ? N2 N1 C8 C7 -25.22(13) . . . . ? C6 C7 C8 N1 -8.07(16) . . . . ? C1 N2 C9 C6 60.66(11) . . . . ? N1 N2 C9 C6 -68.32(10) . . . . ? C7 C6 C9 N2 36.61(13) . . . . ? C5 C6 C9 N2 -130.66(10) . . . . ? N2 N1 C10 C11 -160.04(10) . . . . ? C8 N1 C10 C11 -12.43(16) . . . . ? N2 N1 C10 C15 24.20(15) . . . . ? C8 N1 C10 C15 171.81(10) . . . . ? N1 C10 C11 C12 -174.03(11) . . . . ? C15 C10 C11 C12 1.80(17) . . . . ? C10 C11 C12 C13 -0.38(18) . . . . ? C11 C12 C13 C14 -0.85(19) . . . . ? C12 C13 C14 C15 0.62(19) . . . . ? C13 C14 C15 C10 0.85(18) . . . . ? N1 C10 C15 C14 173.82(11) . . . . ? C11 C10 C15 C14 -2.04(17) . . . . ? _diffrn_measured_fraction_theta_max 0.997 _diffrn_reflns_theta_full 27.10 _diffrn_measured_fraction_theta_full 0.997 _refine_diff_density_max 0.295 _refine_diff_density_min -0.161 _refine_diff_density_rms 0.036