data_2 _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C18 H23 N O2' _chemical_formula_weight 285.37 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 12.580(5) _cell_length_b 15.830(5) _cell_length_c 8.839(5) _cell_angle_alpha 90.000(5) _cell_angle_beta 109.551(5) _cell_angle_gamma 90.000(5) _cell_volume 1658.7(13) _cell_formula_units_Z 4 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 1213 _cell_measurement_theta_min 2.55 _cell_measurement_theta_max 19.80 _exptl_crystal_description block _exptl_crystal_colour colorless _exptl_crystal_size_max 0.25 _exptl_crystal_size_mid 0.10 _exptl_crystal_size_min 0.08 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.143 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 616 _exptl_absorpt_coefficient_mu 0.074 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.9818 _exptl_absorpt_correction_T_max 0.9941 _exptl_absorpt_process_details sadabs _exptl_special_details ; ? ; _diffrn_ambient_temperature 293(2) _diffrn_radiation_wavelength 0.71069 _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 'phi and omega scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_decay_% ? _diffrn_reflns_number 10946 _diffrn_reflns_av_R_equivalents 0.0721 _diffrn_reflns_av_unetI/netI 0.0808 _diffrn_reflns_limit_h_min -16 _diffrn_reflns_limit_h_max 13 _diffrn_reflns_limit_k_min -20 _diffrn_reflns_limit_k_max 19 _diffrn_reflns_limit_l_min -11 _diffrn_reflns_limit_l_max 11 _diffrn_reflns_theta_min 2.15 _diffrn_reflns_theta_max 27.54 _reflns_number_total 3813 _reflns_number_gt 1680 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SMART' _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^)+(0.1854P)^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 constr _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 3813 _refine_ls_number_parameters 193 _refine_ls_number_restraints 1 _refine_ls_R_factor_all 0.1730 _refine_ls_R_factor_gt 0.0912 _refine_ls_wR_factor_ref 0.3260 _refine_ls_wR_factor_gt 0.2590 _refine_ls_goodness_of_fit_ref 0.996 _refine_ls_restrained_S_all 0.999 _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 N1 N 1.2411(2) 0.75737(18) 1.0510(4) 0.0650(8) Uani 1 1 d . . . H11 H 1.2264 0.7716 1.1358 0.078 Uiso 1 1 calc R . . O1 O 0.5812(2) 0.98048(19) 0.3590(4) 0.0834(9) Uani 1 1 d . . . O2 O 1.1820(2) 0.68289(15) 0.8204(3) 0.0675(8) Uani 1 1 d . . . C1 C 0.8860(3) 0.7430(2) 0.7257(4) 0.0589(9) Uani 1 1 d . . . H1 H 0.8798 0.6873 0.6898 0.071 Uiso 1 1 calc R . . C2 C 0.8100(3) 0.8025(2) 0.6339(4) 0.0569(9) Uani 1 1 d . . . C3 C 0.7235(3) 0.7831(3) 0.4882(5) 0.0745(11) Uani 1 1 d . . . H3 H 0.7154 0.7276 0.4513 0.089 Uiso 1 1 calc R . . C4 C 0.6522(3) 0.8426(3) 0.4011(5) 0.0821(12) Uani 1 1 d . . . H4 H 0.5972 0.8279 0.3047 0.099 Uiso 1 1 calc R . . C5 C 0.6607(3) 0.9270(3) 0.4554(4) 0.0653(10) Uani 1 1 d . . . C6 C 0.7444(3) 0.9495(2) 0.5954(4) 0.0599(9) Uani 1 1 d . . . H6 H 0.7511 1.0055 0.6296 0.072 Uiso 1 1 calc R . . C7 C 0.8193(3) 0.8887(2) 0.6865(4) 0.0553(9) Uani 1 1 d . . . C8 C 0.9073(3) 0.9082(2) 0.8312(4) 0.0633(10) Uani 1 1 d . . . H8 H 0.9170 0.9637 0.8677 0.076 Uiso 1 1 calc R . . C9 C 0.9780(3) 0.8472(2) 0.9177(4) 0.0602(9) Uani 1 1 d . . . H9 H 1.0334 0.8620 1.0137 0.072 Uiso 1 1 calc R . . C10 C 0.9698(3) 0.7630(2) 0.8670(4) 0.0545(9) Uani 1 1 d . . . C11 C 0.5833(3) 1.0666(3) 0.4062(6) 0.0843(13) Uani 1 1 d . . . H11A H 0.6518 1.0925 0.4044 0.127 Uiso 1 1 calc R . . H11B H 0.5796 1.0696 0.5128 0.127 Uiso 1 1 calc R . . H11C H 0.5198 1.0957 0.3331 0.127 Uiso 1 1 calc R . . C12 C 1.0529(3) 0.6983(2) 0.9667(4) 0.0587(9) Uani 1 1 d . . . H12 H 1.0645 0.7103 1.0799 0.070 Uiso 1 1 calc R . . C13 C 1.0159(3) 0.6064(2) 0.9359(6) 0.0777(12) Uani 1 1 d . . . H13A H 1.0684 0.5710 1.0140 0.117 Uiso 1 1 calc R . . H13B H 1.0137 0.5903 0.8302 0.117 Uiso 1 1 calc R . . H13C H 0.9422 0.5999 0.9443 0.117 Uiso 1 1 calc R . . C14 C 1.1653(3) 0.7121(2) 0.9402(4) 0.0565(9) Uani 1 1 d . . . C15 C 1.3476(3) 0.7842(3) 1.0367(5) 0.0801(12) Uani 1 1 d . . . H15A H 1.3706 0.7433 0.9720 0.096 Uiso 1 1 calc R . . H15B H 1.4045 0.7845 1.1426 0.096 Uiso 1 1 calc R . . C16 C 1.3438(5) 0.8680(3) 0.9646(9) 0.139(2) Uani 1 1 d D . . H16A H 1.2944 0.8642 0.8538 0.167 Uiso 1 1 calc R . . H16B H 1.4188 0.8803 0.9626 0.167 Uiso 1 1 calc R . . C17 C 1.3065(6) 0.9421(3) 1.0380(10) 0.154(3) Uani 1 1 d D . . H17A H 1.2322 0.9293 1.0426 0.185 Uiso 1 1 calc R . . H17B H 1.3571 0.9470 1.1479 0.185 Uiso 1 1 calc R . . C18 C 1.3005(6) 1.0244(3) 0.9627(10) 0.147(3) Uani 1 1 d . . . H18A H 1.2401 1.0246 0.8616 0.220 Uiso 1 1 calc R . . H18B H 1.3705 1.0359 0.9455 0.220 Uiso 1 1 calc R . . H18C H 1.2869 1.0670 1.0314 0.220 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 N1 0.0634(17) 0.0776(19) 0.0585(19) -0.0044(16) 0.0265(15) -0.0061(16) O1 0.0646(17) 0.094(2) 0.080(2) 0.0065(16) 0.0089(15) 0.0065(15) O2 0.0742(17) 0.0850(17) 0.0507(14) -0.0035(13) 0.0308(12) 0.0043(13) C1 0.062(2) 0.0585(19) 0.059(2) -0.0114(18) 0.0249(17) -0.0074(17) C2 0.0500(19) 0.062(2) 0.060(2) -0.0078(17) 0.0212(16) -0.0057(16) C3 0.065(2) 0.077(2) 0.073(3) -0.017(2) 0.011(2) -0.005(2) C4 0.061(2) 0.095(3) 0.075(3) -0.013(2) 0.001(2) -0.003(2) C5 0.053(2) 0.081(3) 0.061(2) 0.003(2) 0.0171(18) 0.0018(19) C6 0.061(2) 0.063(2) 0.058(2) -0.0052(18) 0.0234(17) -0.0024(18) C7 0.0514(19) 0.063(2) 0.054(2) -0.0047(17) 0.0218(16) -0.0026(16) C8 0.068(2) 0.059(2) 0.061(2) -0.0101(18) 0.0190(19) -0.0055(18) C9 0.061(2) 0.064(2) 0.052(2) -0.0068(17) 0.0145(16) -0.0034(18) C10 0.0555(19) 0.060(2) 0.055(2) -0.0011(17) 0.0268(16) -0.0018(16) C11 0.077(3) 0.078(3) 0.093(3) 0.012(2) 0.022(2) 0.007(2) C12 0.066(2) 0.063(2) 0.054(2) 0.0014(16) 0.0301(17) -0.0004(17) C13 0.073(2) 0.071(2) 0.093(3) 0.007(2) 0.032(2) -0.003(2) C14 0.064(2) 0.0591(19) 0.049(2) 0.0086(16) 0.0212(17) 0.0058(17) C15 0.062(2) 0.090(3) 0.089(3) -0.003(2) 0.026(2) -0.007(2) C16 0.112(4) 0.117(4) 0.224(7) 0.011(5) 0.101(5) -0.018(4) C17 0.157(6) 0.115(5) 0.240(9) -0.014(5) 0.132(6) -0.034(4) C18 0.180(7) 0.094(4) 0.206(8) 0.030(4) 0.117(6) 0.005(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 N1 C14 1.326(4) . ? N1 C15 1.451(5) . ? N1 H11 0.8600 . ? O1 C5 1.368(4) . ? O1 C11 1.423(5) . ? O2 C14 1.236(4) . ? C1 C10 1.375(5) . ? C1 C2 1.393(5) . ? C1 H1 0.9300 . ? C2 C3 1.414(5) . ? C2 C7 1.435(5) . ? C3 C4 1.350(5) . ? C3 H3 0.9300 . ? C4 C5 1.412(6) . ? C4 H4 0.9300 . ? C5 C6 1.376(5) . ? C6 C7 1.398(5) . ? C6 H6 0.9300 . ? C7 C8 1.418(5) . ? C8 C9 1.361(5) . ? C8 H8 0.9300 . ? C9 C10 1.399(4) . ? C9 H9 0.9300 . ? C10 C12 1.517(5) . ? C11 H11A 0.9600 . ? C11 H11B 0.9600 . ? C11 H11C 0.9600 . ? C12 C13 1.524(5) . ? C12 C14 1.525(5) . ? C12 H12 0.9800 . ? C13 H13A 0.9600 . ? C13 H13B 0.9600 . ? C13 H13C 0.9600 . ? C15 C16 1.465(7) . ? C15 H15A 0.9700 . ? C15 H15B 0.9700 . ? C16 C17 1.490(2) . ? C16 H16A 0.9700 . ? C16 H16B 0.9700 . ? C17 C18 1.453(8) . ? C17 H17A 0.9700 . ? C17 H17B 0.9700 . ? C18 H18A 0.9600 . ? C18 H18B 0.9600 . ? C18 H18C 0.9600 . ? 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 C14 N1 C15 123.4(3) . . ? C14 N1 H11 118.3 . . ? C15 N1 H11 118.3 . . ? C5 O1 C11 118.1(3) . . ? C10 C1 C2 122.8(3) . . ? C10 C1 H1 118.6 . . ? C2 C1 H1 118.6 . . ? C1 C2 C3 123.6(3) . . ? C1 C2 C7 119.3(3) . . ? C3 C2 C7 117.1(3) . . ? C4 C3 C2 122.0(4) . . ? C4 C3 H3 119.0 . . ? C2 C3 H3 119.0 . . ? C3 C4 C5 120.4(4) . . ? C3 C4 H4 119.8 . . ? C5 C4 H4 119.8 . . ? O1 C5 C6 125.4(4) . . ? O1 C5 C4 114.7(3) . . ? C6 C5 C4 119.9(4) . . ? C5 C6 C7 120.3(3) . . ? C5 C6 H6 119.9 . . ? C7 C6 H6 119.9 . . ? C6 C7 C8 122.8(3) . . ? C6 C7 C2 120.2(3) . . ? C8 C7 C2 116.9(3) . . ? C9 C8 C7 121.3(3) . . ? C9 C8 H8 119.4 . . ? C7 C8 H8 119.4 . . ? C8 C9 C10 122.1(3) . . ? C8 C9 H9 118.9 . . ? C10 C9 H9 118.9 . . ? C1 C10 C9 117.5(3) . . ? C1 C10 C12 122.8(3) . . ? C9 C10 C12 119.7(3) . . ? O1 C11 H11A 109.5 . . ? O1 C11 H11B 109.5 . . ? H11A C11 H11B 109.5 . . ? O1 C11 H11C 109.5 . . ? H11A C11 H11C 109.5 . . ? H11B C11 H11C 109.5 . . ? C10 C12 C13 115.5(3) . . ? C10 C12 C14 107.9(3) . . ? C13 C12 C14 110.7(3) . . ? C10 C12 H12 107.5 . . ? C13 C12 H12 107.5 . . ? C14 C12 H12 107.5 . . ? C12 C13 H13A 109.5 . . ? C12 C13 H13B 109.5 . . ? H13A C13 H13B 109.5 . . ? C12 C13 H13C 109.5 . . ? H13A C13 H13C 109.5 . . ? H13B C13 H13C 109.5 . . ? O2 C14 N1 123.3(3) . . ? O2 C14 C12 120.7(3) . . ? N1 C14 C12 116.0(3) . . ? N1 C15 C16 114.0(4) . . ? N1 C15 H15A 108.8 . . ? C16 C15 H15A 108.8 . . ? N1 C15 H15B 108.8 . . ? C16 C15 H15B 108.8 . . ? H15A C15 H15B 107.7 . . ? C15 C16 C17 119.5(5) . . ? C15 C16 H16A 107.4 . . ? C17 C16 H16A 107.4 . . ? C15 C16 H16B 107.4 . . ? C17 C16 H16B 107.4 . . ? H16A C16 H16B 107.0 . . ? C18 C17 C16 118.8(6) . . ? C18 C17 H17A 107.6 . . ? C16 C17 H17A 107.6 . . ? C18 C17 H17B 107.6 . . ? C16 C17 H17B 107.6 . . ? H17A C17 H17B 107.0 . . ? C17 C18 H18A 109.5 . . ? C17 C18 H18B 109.5 . . ? H18A C18 H18B 109.5 . . ? C17 C18 H18C 109.5 . . ? H18A C18 H18C 109.5 . . ? H18B C18 H18C 109.5 . . ? 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 C10 C1 C2 C3 179.9(3) . . . . ? C10 C1 C2 C7 0.7(5) . . . . ? C1 C2 C3 C4 -179.1(4) . . . . ? C7 C2 C3 C4 0.1(6) . . . . ? C2 C3 C4 C5 -1.3(6) . . . . ? C11 O1 C5 C6 -0.5(5) . . . . ? C11 O1 C5 C4 179.4(3) . . . . ? C3 C4 C5 O1 -177.9(4) . . . . ? C3 C4 C5 C6 2.0(6) . . . . ? O1 C5 C6 C7 178.2(3) . . . . ? C4 C5 C6 C7 -1.7(5) . . . . ? C5 C6 C7 C8 179.7(3) . . . . ? C5 C6 C7 C2 0.5(5) . . . . ? C1 C2 C7 C6 179.5(3) . . . . ? C3 C2 C7 C6 0.3(5) . . . . ? C1 C2 C7 C8 0.2(5) . . . . ? C3 C2 C7 C8 -179.0(3) . . . . ? C6 C7 C8 C9 179.3(3) . . . . ? C2 C7 C8 C9 -1.5(5) . . . . ? C7 C8 C9 C10 1.8(5) . . . . ? C2 C1 C10 C9 -0.5(5) . . . . ? C2 C1 C10 C12 -179.8(3) . . . . ? C8 C9 C10 C1 -0.8(5) . . . . ? C8 C9 C10 C12 178.5(3) . . . . ? C1 C10 C12 C13 -20.3(4) . . . . ? C9 C10 C12 C13 160.4(3) . . . . ? C1 C10 C12 C14 104.2(3) . . . . ? C9 C10 C12 C14 -75.2(4) . . . . ? C15 N1 C14 O2 5.9(6) . . . . ? C15 N1 C14 C12 -173.3(3) . . . . ? C10 C12 C14 O2 -81.5(4) . . . . ? C13 C12 C14 O2 45.8(4) . . . . ? C10 C12 C14 N1 97.7(4) . . . . ? C13 C12 C14 N1 -135.0(3) . . . . ? C14 N1 C15 C16 92.5(5) . . . . ? N1 C15 C16 C17 56.2(8) . . . . ? C15 C16 C17 C18 -178.5(6) . . . . ? _diffrn_measured_fraction_theta_max 0.996 _diffrn_reflns_theta_full 27.54 _diffrn_measured_fraction_theta_full 0.996 _refine_diff_density_max 0.576 _refine_diff_density_min -0.450 _refine_diff_density_rms 0.066