data_a _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C18 H19 N O3' _chemical_formula_weight 297.34 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 14.400(3) _cell_length_b 7.7917(16) _cell_length_c 13.790(3) _cell_angle_alpha 90.00 _cell_angle_beta 98.05(3) _cell_angle_gamma 90.00 _cell_volume 1532.0(5) _cell_formula_units_Z 4 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 6618 _cell_measurement_theta_min 1.43 _cell_measurement_theta_max 27.44 _exptl_crystal_description prism _exptl_crystal_colour colorless _exptl_crystal_size_max 0.95 _exptl_crystal_size_mid 0.55 _exptl_crystal_size_min 0.48 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.289 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 632 _exptl_absorpt_coefficient_mu 0.088 _exptl_absorpt_correction_type empirical _exptl_absorpt_correction_T_min 0.9213 _exptl_absorpt_correction_T_max 0.9591 _exptl_absorpt_process_details abscor _exptl_special_details ; ? ; _diffrn_ambient_temperature 293(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'Rotating Anode' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Rigaku Raxis Rapid IP' _diffrn_measurement_method oscillation _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 6618 _diffrn_reflns_av_R_equivalents 0.0338 _diffrn_reflns_av_sigmaI/netI 0.0419 _diffrn_reflns_limit_h_min -17 _diffrn_reflns_limit_h_max 17 _diffrn_reflns_limit_k_min -9 _diffrn_reflns_limit_k_max 9 _diffrn_reflns_limit_l_min -16 _diffrn_reflns_limit_l_max 16 _diffrn_reflns_theta_min 1.43 _diffrn_reflns_theta_max 25.00 _reflns_number_total 2692 _reflns_number_gt 2068 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Rapid Auto(Rigaku 2001)' _computing_cell_refinement 'Rapid Auto(Rigaku 2001)' _computing_data_reduction 'Rapid Auto(Rigaku 2001)' _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^)+(0.0913P)^2^+0.6456P] 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 0.0085(6) _refine_ls_number_reflns 2692 _refine_ls_number_parameters 200 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0850 _refine_ls_R_factor_gt 0.0636 _refine_ls_wR_factor_ref 0.1749 _refine_ls_wR_factor_gt 0.1641 _refine_ls_goodness_of_fit_ref 1.085 _refine_ls_restrained_S_all 1.085 _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 O2 O 0.95521(14) 0.0879(2) 0.38205(14) 0.0490(6) Uani 1 1 d . . . H2A H 0.9599 0.1303 0.4369 0.073 Uiso 1 1 calc R . . N1 N 0.90214(15) -0.3316(3) 0.31945(15) 0.0346(5) Uani 1 1 d . . . O3 O 0.83118(16) -0.4685(3) 0.12331(16) 0.0576(6) Uani 1 1 d . . . H3A H 0.8839 -0.5016 0.1164 0.086 Uiso 1 1 calc R . . C3 C 0.83074(17) -0.0624(3) 0.27681(17) 0.0317(6) Uani 1 1 d . . . H3B H 0.8646 -0.0070 0.2284 0.038 Uiso 1 1 calc R . . C4 C 0.82434(17) -0.2574(3) 0.25237(18) 0.0318(6) Uani 1 1 d . . . H4A H 0.7645 -0.3035 0.2671 0.038 Uiso 1 1 calc R . . O1 O 1.01488(14) -0.2548(3) 0.44488(15) 0.0592(6) Uani 1 1 d . . . C6 C 0.73708(18) 0.0287(3) 0.27411(18) 0.0345(6) Uani 1 1 d . . . C13 C 0.75705(18) -0.2026(3) 0.07622(18) 0.0369(6) Uani 1 1 d . . . C2 C 0.89341(18) -0.0526(3) 0.37664(18) 0.0343(6) Uani 1 1 d . . . H2B H 0.8541 -0.0440 0.4289 0.041 Uiso 1 1 calc R . . C12 C 0.83377(18) -0.2896(3) 0.14414(19) 0.0378(6) Uani 1 1 d . . . H12A H 0.8943 -0.2440 0.1313 0.045 Uiso 1 1 calc R . . C14 C 0.7770(2) -0.0680(4) 0.0170(2) 0.0474(7) Uani 1 1 d . . . H14A H 0.8384 -0.0291 0.0195 0.057 Uiso 1 1 calc R . . C5 C 0.9221(2) -0.5157(3) 0.3251(2) 0.0450(7) Uani 1 1 d . . . H5A H 0.9751 -0.5364 0.3741 0.068 Uiso 1 1 calc R . . H5B H 0.9358 -0.5556 0.2627 0.068 Uiso 1 1 calc R . . H5C H 0.8685 -0.5759 0.3421 0.068 Uiso 1 1 calc R . . C11 C 0.6734(2) -0.0228(4) 0.3353(2) 0.0473(7) Uani 1 1 d . . . H11A H 0.6884 -0.1136 0.3785 0.057 Uiso 1 1 calc R . . C1 C 0.94488(18) -0.2221(4) 0.38463(19) 0.0376(6) Uani 1 1 d . . . C18 C 0.66491(19) -0.2567(4) 0.0713(2) 0.0466(7) Uani 1 1 d . . . H18A H 0.6503 -0.3459 0.1114 0.056 Uiso 1 1 calc R . . C7 C 0.7136(2) 0.1650(4) 0.2116(2) 0.0471(7) Uani 1 1 d . . . H7A H 0.7554 0.2029 0.1706 0.056 Uiso 1 1 calc R . . C17 C 0.5943(2) -0.1799(5) 0.0078(2) 0.0576(9) Uani 1 1 d . . . H17A H 0.5328 -0.2184 0.0049 0.069 Uiso 1 1 calc R . . C9 C 0.5640(2) 0.1923(4) 0.2702(3) 0.0627(10) Uani 1 1 d . . . H9A H 0.5061 0.2461 0.2682 0.075 Uiso 1 1 calc R . . C16 C 0.6146(3) -0.0470(5) -0.0511(2) 0.0625(10) Uani 1 1 d . . . H16A H 0.5670 0.0045 -0.0938 0.075 Uiso 1 1 calc R . . C10 C 0.5882(2) 0.0589(4) 0.3329(3) 0.0577(9) Uani 1 1 d . . . H10A H 0.5466 0.0226 0.3745 0.069 Uiso 1 1 calc R . . C15 C 0.7048(3) 0.0095(5) -0.0467(2) 0.0605(9) Uani 1 1 d . . . H15A H 0.7184 0.1002 -0.0862 0.073 Uiso 1 1 calc R . . C8 C 0.6268(3) 0.2458(4) 0.2099(3) 0.0651(10) Uani 1 1 d . . . H8A H 0.6112 0.3373 0.1674 0.078 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 O2 0.0548(13) 0.0454(11) 0.0451(11) -0.0037(9) 0.0015(9) -0.0177(9) N1 0.0370(12) 0.0342(11) 0.0312(11) 0.0041(9) -0.0001(9) 0.0058(9) O3 0.0659(14) 0.0509(13) 0.0531(13) -0.0130(10) -0.0017(10) 0.0189(11) C3 0.0345(14) 0.0328(13) 0.0276(13) 0.0027(10) 0.0040(10) -0.0011(10) C4 0.0299(13) 0.0322(13) 0.0322(13) 0.0018(11) 0.0003(10) 0.0013(10) O1 0.0539(13) 0.0614(14) 0.0541(13) -0.0069(11) -0.0211(11) 0.0141(11) C6 0.0377(14) 0.0291(13) 0.0345(14) -0.0036(11) -0.0026(11) 0.0017(11) C13 0.0404(15) 0.0446(15) 0.0253(13) -0.0049(11) 0.0027(11) 0.0077(12) C2 0.0355(14) 0.0356(14) 0.0312(13) -0.0018(11) 0.0028(11) -0.0044(11) C12 0.0367(14) 0.0415(15) 0.0350(14) -0.0020(11) 0.0040(11) 0.0053(11) C14 0.0514(17) 0.0544(18) 0.0372(15) 0.0033(14) 0.0091(13) 0.0062(14) C5 0.0559(18) 0.0374(15) 0.0402(15) 0.0040(13) 0.0012(13) 0.0118(13) C11 0.0414(16) 0.0422(16) 0.0588(19) 0.0018(14) 0.0093(14) 0.0026(13) C1 0.0361(14) 0.0430(15) 0.0323(14) 0.0015(12) -0.0004(12) 0.0018(12) C18 0.0449(17) 0.0522(17) 0.0414(16) -0.0023(14) 0.0016(13) 0.0045(14) C7 0.0546(18) 0.0394(15) 0.0446(16) 0.0017(13) -0.0021(13) 0.0047(13) C17 0.0425(18) 0.072(2) 0.0542(19) -0.0105(17) -0.0054(14) 0.0114(16) C9 0.0446(18) 0.059(2) 0.081(3) -0.0181(19) -0.0042(18) 0.0136(16) C16 0.062(2) 0.079(3) 0.0430(18) 0.0022(17) -0.0044(15) 0.0327(19) C10 0.0384(17) 0.056(2) 0.079(2) -0.0120(18) 0.0099(16) 0.0006(14) C15 0.079(3) 0.062(2) 0.0399(17) 0.0122(16) 0.0092(16) 0.0192(19) C8 0.077(2) 0.0429(18) 0.067(2) 0.0016(17) -0.0202(19) 0.0225(18) _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 O2 C2 1.406(3) . ? O2 H2A 0.8200 . ? N1 C1 1.327(3) . ? N1 C5 1.463(3) . ? N1 C4 1.468(3) . ? O3 C12 1.422(3) . ? O3 H3A 0.8200 . ? C3 C6 1.520(4) . ? C3 C2 1.539(3) . ? C3 C4 1.556(3) . ? C3 H3B 0.9800 . ? C4 C12 1.538(4) . ? C4 H4A 0.9800 . ? O1 C1 1.240(3) . ? C6 C7 1.380(4) . ? C6 C11 1.390(4) . ? C13 C14 1.383(4) . ? C13 C18 1.385(4) . ? C13 C12 1.506(4) . ? C2 C1 1.510(4) . ? C2 H2B 0.9800 . ? C12 H12A 0.9800 . ? C14 C15 1.401(4) . ? C14 H14A 0.9300 . ? C5 H5A 0.9600 . ? C5 H5B 0.9600 . ? C5 H5C 0.9600 . ? C11 C10 1.378(4) . ? C11 H11A 0.9300 . ? C18 C17 1.382(4) . ? C18 H18A 0.9300 . ? C7 C8 1.396(4) . ? C7 H7A 0.9300 . ? C17 C16 1.372(5) . ? C17 H17A 0.9300 . ? C9 C10 1.366(5) . ? C9 C8 1.375(5) . ? C9 H9A 0.9300 . ? C16 C15 1.365(5) . ? C16 H16A 0.9300 . ? C10 H10A 0.9300 . ? C15 H15A 0.9300 . ? C8 H8A 0.9300 . ? 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 O2 H2A 109.5 . . ? C1 N1 C5 121.7(2) . . ? C1 N1 C4 114.5(2) . . ? C5 N1 C4 123.1(2) . . ? C12 O3 H3A 109.5 . . ? C6 C3 C2 114.0(2) . . ? C6 C3 C4 115.2(2) . . ? C2 C3 C4 104.57(19) . . ? C6 C3 H3B 107.6 . . ? C2 C3 H3B 107.6 . . ? C4 C3 H3B 107.6 . . ? N1 C4 C12 112.6(2) . . ? N1 C4 C3 103.38(19) . . ? C12 C4 C3 111.0(2) . . ? N1 C4 H4A 109.9 . . ? C12 C4 H4A 109.9 . . ? C3 C4 H4A 109.9 . . ? C7 C6 C11 118.5(3) . . ? C7 C6 C3 120.9(2) . . ? C11 C6 C3 120.6(2) . . ? C14 C13 C18 118.6(3) . . ? C14 C13 C12 120.9(3) . . ? C18 C13 C12 120.5(3) . . ? O2 C2 C1 112.1(2) . . ? O2 C2 C3 111.9(2) . . ? C1 C2 C3 104.0(2) . . ? O2 C2 H2B 109.5 . . ? C1 C2 H2B 109.5 . . ? C3 C2 H2B 109.5 . . ? O3 C12 C13 108.6(2) . . ? O3 C12 C4 110.6(2) . . ? C13 C12 C4 111.9(2) . . ? O3 C12 H12A 108.5 . . ? C13 C12 H12A 108.5 . . ? C4 C12 H12A 108.5 . . ? C13 C14 C15 120.0(3) . . ? C13 C14 H14A 120.0 . . ? C15 C14 H14A 120.0 . . ? N1 C5 H5A 109.5 . . ? N1 C5 H5B 109.5 . . ? H5A C5 H5B 109.5 . . ? N1 C5 H5C 109.5 . . ? H5A C5 H5C 109.5 . . ? H5B C5 H5C 109.5 . . ? C10 C11 C6 120.8(3) . . ? C10 C11 H11A 119.6 . . ? C6 C11 H11A 119.6 . . ? O1 C1 N1 125.3(3) . . ? O1 C1 C2 125.0(2) . . ? N1 C1 C2 109.7(2) . . ? C17 C18 C13 120.9(3) . . ? C17 C18 H18A 119.5 . . ? C13 C18 H18A 119.5 . . ? C6 C7 C8 119.8(3) . . ? C6 C7 H7A 120.1 . . ? C8 C7 H7A 120.1 . . ? C16 C17 C18 120.2(3) . . ? C16 C17 H17A 119.9 . . ? C18 C17 H17A 119.9 . . ? C10 C9 C8 118.8(3) . . ? C10 C9 H9A 120.6 . . ? C8 C9 H9A 120.6 . . ? C15 C16 C17 119.8(3) . . ? C15 C16 H16A 120.1 . . ? C17 C16 H16A 120.1 . . ? C9 C10 C11 120.9(3) . . ? C9 C10 H10A 119.5 . . ? C11 C10 H10A 119.5 . . ? C16 C15 C14 120.5(3) . . ? C16 C15 H15A 119.8 . . ? C14 C15 H15A 119.8 . . ? C9 C8 C7 121.1(3) . . ? C9 C8 H8A 119.5 . . ? C7 C8 H8A 119.5 . . ? 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 C1 N1 C4 C12 127.2(2) . . . . ? C5 N1 C4 C12 -62.1(3) . . . . ? C1 N1 C4 C3 7.3(3) . . . . ? C5 N1 C4 C3 178.0(2) . . . . ? C6 C3 C4 N1 -142.4(2) . . . . ? C2 C3 C4 N1 -16.5(2) . . . . ? C6 C3 C4 C12 96.7(3) . . . . ? C2 C3 C4 C12 -137.4(2) . . . . ? C2 C3 C6 C7 118.5(3) . . . . ? C4 C3 C6 C7 -120.6(3) . . . . ? C2 C3 C6 C11 -61.0(3) . . . . ? C4 C3 C6 C11 59.9(3) . . . . ? C6 C3 C2 O2 -92.6(3) . . . . ? C4 C3 C2 O2 140.8(2) . . . . ? C6 C3 C2 C1 146.1(2) . . . . ? C4 C3 C2 C1 19.5(3) . . . . ? C14 C13 C12 O3 -124.6(3) . . . . ? C18 C13 C12 O3 55.0(3) . . . . ? C14 C13 C12 C4 113.0(3) . . . . ? C18 C13 C12 C4 -67.4(3) . . . . ? N1 C4 C12 O3 62.6(3) . . . . ? C3 C4 C12 O3 177.9(2) . . . . ? N1 C4 C12 C13 -176.1(2) . . . . ? C3 C4 C12 C13 -60.8(3) . . . . ? C18 C13 C14 C15 -0.5(4) . . . . ? C12 C13 C14 C15 179.1(3) . . . . ? C7 C6 C11 C10 0.7(4) . . . . ? C3 C6 C11 C10 -179.7(3) . . . . ? C5 N1 C1 O1 12.9(4) . . . . ? C4 N1 C1 O1 -176.3(3) . . . . ? C5 N1 C1 C2 -165.3(2) . . . . ? C4 N1 C1 C2 5.6(3) . . . . ? O2 C2 C1 O1 44.6(4) . . . . ? C3 C2 C1 O1 165.8(3) . . . . ? O2 C2 C1 N1 -137.2(2) . . . . ? C3 C2 C1 N1 -16.1(3) . . . . ? C14 C13 C18 C17 0.9(4) . . . . ? C12 C13 C18 C17 -178.7(3) . . . . ? C11 C6 C7 C8 -0.9(4) . . . . ? C3 C6 C7 C8 179.5(3) . . . . ? C13 C18 C17 C16 -0.6(5) . . . . ? C18 C17 C16 C15 -0.1(5) . . . . ? C8 C9 C10 C11 -0.8(5) . . . . ? C6 C11 C10 C9 0.2(5) . . . . ? C17 C16 C15 C14 0.5(5) . . . . ? C13 C14 C15 C16 -0.2(5) . . . . ? C10 C9 C8 C7 0.6(5) . . . . ? C6 C7 C8 C9 0.3(5) . . . . ? _diffrn_measured_fraction_theta_max 0.998 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 0.998 _refine_diff_density_max 0.298 _refine_diff_density_min -0.316 _refine_diff_density_rms 0.081