data_q52c _audit_creation_method SHELXTL _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C16 H25 N O2' _chemical_formula_weight 263.37 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source 'C' 'C' 0.0181 0.0091 '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' 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 'O' 'O' 0.0492 0.0322 '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)/n loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, y+1/2, -z+1/2' '-x, -y, -z' 'x-1/2, -y-1/2, z-1/2' _cell_length_a 9.7778(6) _cell_length_b 8.0904(5) _cell_length_c 18.0100(11) _cell_angle_alpha 90.00 _cell_angle_beta 94.851(2) _cell_angle_gamma 90.00 _cell_volume 1419.60(15) _cell_formula_units_Z 4 _cell_measurement_temperature 100(2) _cell_measurement_reflns_used 9982 _cell_measurement_theta_min 2.46 _cell_measurement_theta_max 68.89 _exptl_crystal_description Rectangualr _exptl_crystal_colour colourless _exptl_crystal_size_max 0.32 _exptl_crystal_size_mid 0.16 _exptl_crystal_size_min 0.06 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.232 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 576 _exptl_absorpt_coefficient_mu 0.630 _exptl_absorpt_correction_type Multi-scan _exptl_absorpt_correction_T_min 0.820 _exptl_absorpt_correction_T_max 1.000 _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 100(2) _diffrn_radiation_wavelength 1.54178 _diffrn_radiation_type CuK\a _diffrn_radiation_source 'Bruker MicroStar microfocus rotating anode' _diffrn_radiation_monochromator 'Helios multilayer optics' _diffrn_measurement_device_type 'Bruker APEX-II CCD' _diffrn_measurement_method '\f and \w scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number 0 _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% 0.00 _diffrn_reflns_number 10332 _diffrn_reflns_av_R_equivalents 0.0437 _diffrn_reflns_av_sigmaI/netI 0.0395 _diffrn_reflns_limit_h_min -11 _diffrn_reflns_limit_h_max 11 _diffrn_reflns_limit_k_min -9 _diffrn_reflns_limit_k_max 8 _diffrn_reflns_limit_l_min -21 _diffrn_reflns_limit_l_max 21 _diffrn_reflns_theta_min 4.93 _diffrn_reflns_theta_max 69.27 _reflns_number_total 2502 _reflns_number_gt 2494 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker APEX2' _computing_cell_refinement 'Bruker 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^)+(0.0126P)^2^+13.2232P] 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 2502 _refine_ls_number_parameters 261 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.1082 _refine_ls_R_factor_gt 0.1081 _refine_ls_wR_factor_ref 0.2422 _refine_ls_wR_factor_gt 0.2422 _refine_ls_goodness_of_fit_ref 1.007 _refine_ls_restrained_S_all 1.007 _refine_ls_shift/su_max 0.001 _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 0.2661(4) 0.5933(5) 0.58932(19) 0.0320(9) Uani 1 1 d . . . O2 O 0.2090(4) 0.3143(5) 0.20613(19) 0.0363(10) Uani 1 1 d . . . N N 0.2736(4) 0.3870(5) 0.5063(2) 0.0201(9) Uani 1 1 d . . . C1 C 0.2532(4) 0.5478(6) 0.5236(3) 0.0219(10) Uani 1 1 d . . . C2 C 0.2124(5) 0.6733(6) 0.4628(3) 0.0272(11) Uani 1 1 d . . . H2A H 0.199(4) 0.790(6) 0.488(2) 0.007(10) Uiso 1 1 d . . . H2B H 0.279(6) 0.688(7) 0.435(3) 0.035(16) Uiso 1 1 d . . . C3 C 0.0782(5) 0.6335(6) 0.4175(3) 0.0222(10) Uani 1 1 d . . . H3A H 0.012(5) 0.602(6) 0.454(3) 0.015(12) Uiso 1 1 d . . . H3B H 0.047(5) 0.737(6) 0.390(3) 0.017(12) Uiso 1 1 d . . . C4 C 0.0892(5) 0.4989(6) 0.3592(2) 0.0202(10) Uani 1 1 d . . . H4A H 0.158(6) 0.534(7) 0.322(3) 0.034(15) Uiso 1 1 d . . . H4B H 0.007(7) 0.478(9) 0.332(4) 0.06(2) Uiso 1 1 d . . . C5 C 0.1241(4) 0.3230(6) 0.3872(2) 0.0157(9) Uani 1 1 d . . . H5 H 0.058(5) 0.286(6) 0.418(2) 0.008(11) Uiso 1 1 d . . . C6 C 0.1220(5) 0.2064(6) 0.3181(2) 0.0199(10) Uani 1 1 d . . . H6 H 0.163(5) 0.105(6) 0.337(2) 0.008(11) Uiso 1 1 d . . . C7 C 0.2323(5) 0.2680(6) 0.2704(3) 0.0229(10) Uani 1 1 d . . . C8 C 0.3758(5) 0.2696(7) 0.3098(3) 0.0298(12) Uani 1 1 d . . . H8A H 0.418(5) 0.158(7) 0.317(3) 0.017(12) Uiso 1 1 d . . . H8B H 0.436(6) 0.318(7) 0.275(3) 0.037(16) Uiso 1 1 d . . . C9 C 0.3823(5) 0.3537(7) 0.3868(3) 0.0289(12) Uani 1 1 d . . . H9A H 0.386(6) 0.480(8) 0.382(3) 0.035(16) Uiso 1 1 d . . . H9B H 0.467(6) 0.317(7) 0.410(3) 0.034(15) Uiso 1 1 d . . . C10 C 0.2645(4) 0.3006(6) 0.4327(2) 0.0177(10) Uani 1 1 d . . . C11 C 0.2812(5) 0.1179(6) 0.4589(3) 0.0240(11) Uani 1 1 d . . . H11A H 0.191(6) 0.073(7) 0.471(3) 0.028(14) Uiso 1 1 d . . . H11B H 0.318(5) 0.044(6) 0.421(3) 0.015(12) Uiso 1 1 d . . . C12 C 0.3716(6) 0.1249(7) 0.5319(3) 0.0300(12) Uani 1 1 d . . . H12A H 0.370(5) 0.031(7) 0.563(3) 0.026(14) Uiso 1 1 d . . . H12B H 0.464(7) 0.153(9) 0.524(4) 0.06(2) Uiso 1 1 d . . . C13 C 0.3153(5) 0.2754(6) 0.5690(3) 0.0263(11) Uani 1 1 d . . . H13A H 0.238(6) 0.249(7) 0.603(3) 0.032(15) Uiso 1 1 d . . . H13B H 0.392(5) 0.339(6) 0.603(3) 0.021(13) Uiso 1 1 d . . . C14 C -0.0174(5) 0.1862(6) 0.2743(3) 0.0234(10) Uani 1 1 d . . . H14A H -0.047(5) 0.283(6) 0.252(2) 0.009(11) Uiso 1 1 d . . . H14B H 0.002(5) 0.102(7) 0.230(3) 0.027(14) Uiso 1 1 d . . . C15 C -0.1240(5) 0.1011(7) 0.3175(3) 0.0274(11) Uani 1 1 d . . . H15B H -0.128(5) 0.171(7) 0.363(3) 0.026(14) Uiso 1 1 d . . . H15A H -0.074(6) -0.010(7) 0.336(3) 0.030(14) Uiso 1 1 d . . . C16 C -0.2621(6) 0.0889(7) 0.2725(3) 0.0367(13) Uani 1 1 d . . . H16A H -0.2984 0.2002 0.2621 0.055 Uiso 1 1 calc R . . H16B H -0.3262 0.0269 0.3009 0.055 Uiso 1 1 calc R . . H16C H -0.2509 0.0318 0.2254 0.055 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 0.035(2) 0.030(2) 0.0297(19) -0.0140(16) -0.0041(15) 0.0033(16) O2 0.057(3) 0.030(2) 0.0246(19) 0.0023(15) 0.0171(17) 0.0062(18) N 0.0180(18) 0.016(2) 0.024(2) -0.0055(16) -0.0055(15) 0.0014(15) C1 0.013(2) 0.022(3) 0.030(3) -0.009(2) -0.0017(18) -0.0006(18) C2 0.029(3) 0.016(3) 0.038(3) -0.002(2) 0.010(2) -0.004(2) C3 0.028(3) 0.014(2) 0.024(2) 0.0014(19) 0.001(2) 0.0030(19) C4 0.025(2) 0.018(3) 0.017(2) 0.0024(18) 0.0009(19) 0.0055(19) C5 0.017(2) 0.016(2) 0.015(2) 0.0006(17) 0.0013(17) 0.0018(17) C6 0.026(2) 0.015(2) 0.019(2) 0.0001(18) 0.0022(18) 0.0026(19) C7 0.034(3) 0.015(2) 0.022(2) -0.0031(18) 0.0107(19) 0.0032(19) C8 0.024(3) 0.026(3) 0.042(3) -0.008(2) 0.016(2) -0.003(2) C9 0.018(2) 0.023(3) 0.046(3) -0.008(2) 0.011(2) -0.004(2) C10 0.016(2) 0.016(2) 0.021(2) -0.0053(17) 0.0007(17) 0.0003(17) C11 0.025(2) 0.020(3) 0.026(2) -0.004(2) -0.007(2) 0.004(2) C12 0.032(3) 0.024(3) 0.031(3) -0.006(2) -0.013(2) 0.010(2) C13 0.030(3) 0.024(3) 0.023(2) -0.007(2) -0.009(2) 0.007(2) C14 0.031(3) 0.017(3) 0.021(2) -0.0005(19) -0.0042(19) 0.005(2) C15 0.030(3) 0.028(3) 0.023(2) -0.006(2) -0.007(2) -0.001(2) C16 0.034(3) 0.030(3) 0.044(3) -0.005(2) -0.014(2) -0.002(2) _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 1.236(6) . ? O2 C7 1.219(6) . ? N C1 1.356(6) . ? N C13 1.476(6) . ? N C10 1.495(5) . ? C1 C2 1.522(7) . ? C2 C3 1.520(7) . ? C2 H2A 1.06(5) . ? C2 H2B 0.87(6) . ? C3 C4 1.523(6) . ? C3 H3A 0.99(5) . ? C3 H3B 1.01(5) . ? C4 C5 1.538(6) . ? C4 H4A 1.03(6) . ? C4 H4B 0.92(7) . ? C5 C10 1.548(6) . ? C5 C6 1.561(6) . ? C5 H5 0.93(5) . ? C6 C7 1.518(6) . ? C6 C14 1.525(6) . ? C6 H6 0.96(5) . ? C7 C8 1.519(7) . ? C8 C9 1.541(7) . ? C8 H8A 1.00(5) . ? C8 H8B 0.97(6) . ? C9 C10 1.534(6) . ? C9 H9A 1.02(6) . ? C9 H9B 0.94(6) . ? C10 C11 1.556(7) . ? C11 C12 1.522(6) . ? C11 H11A 0.99(6) . ? C11 H11B 1.00(5) . ? C12 C13 1.514(7) . ? C12 H12A 0.94(6) . ? C12 H12B 0.95(7) . ? C13 H13A 1.03(6) . ? C13 H13B 1.06(5) . ? C14 C15 1.519(7) . ? C14 H14A 0.92(5) . ? C14 H14B 1.08(5) . ? C15 C16 1.519(7) . ? C15 H15B 0.99(5) . ? C15 H15A 1.06(6) . ? C16 H16A 0.9800 . ? C16 H16B 0.9800 . ? C16 H16C 0.9800 . ? 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 C1 N C13 116.6(4) . . ? C1 N C10 130.7(4) . . ? C13 N C10 112.6(4) . . ? O1 C1 N 120.0(5) . . ? O1 C1 C2 119.3(4) . . ? N C1 C2 120.7(4) . . ? C3 C2 C1 114.0(4) . . ? C3 C2 H2A 107(2) . . ? C1 C2 H2A 109(2) . . ? C3 C2 H2B 112(4) . . ? C1 C2 H2B 110(4) . . ? H2A C2 H2B 105(5) . . ? C2 C3 C4 114.4(4) . . ? C2 C3 H3A 106(3) . . ? C4 C3 H3A 111(3) . . ? C2 C3 H3B 107(3) . . ? C4 C3 H3B 107(3) . . ? H3A C3 H3B 111(4) . . ? C3 C4 C5 117.5(4) . . ? C3 C4 H4A 110(3) . . ? C5 C4 H4A 109(3) . . ? C3 C4 H4B 112(4) . . ? C5 C4 H4B 100(5) . . ? H4A C4 H4B 107(5) . . ? C4 C5 C10 116.3(4) . . ? C4 C5 C6 108.0(3) . . ? C10 C5 C6 107.6(3) . . ? C4 C5 H5 110(3) . . ? C10 C5 H5 106(3) . . ? C6 C5 H5 108(3) . . ? C7 C6 C14 112.9(4) . . ? C7 C6 C5 106.9(4) . . ? C14 C6 C5 115.4(4) . . ? C7 C6 H6 100(3) . . ? C14 C6 H6 115(3) . . ? C5 C6 H6 105(3) . . ? O2 C7 C6 123.6(5) . . ? O2 C7 C8 122.1(4) . . ? C6 C7 C8 114.3(4) . . ? C7 C8 C9 113.0(4) . . ? C7 C8 H8A 114(3) . . ? C9 C8 H8A 107(3) . . ? C7 C8 H8B 107(3) . . ? C9 C8 H8B 115(3) . . ? H8A C8 H8B 101(4) . . ? C10 C9 C8 112.6(4) . . ? C10 C9 H9A 111(3) . . ? C8 C9 H9A 111(3) . . ? C10 C9 H9B 110(4) . . ? C8 C9 H9B 103(4) . . ? H9A C9 H9B 108(5) . . ? N C10 C9 110.9(4) . . ? N C10 C5 113.4(3) . . ? C9 C10 C5 110.8(4) . . ? N C10 C11 100.2(3) . . ? C9 C10 C11 111.4(4) . . ? C5 C10 C11 109.7(4) . . ? C12 C11 C10 105.4(4) . . ? C12 C11 H11A 107(3) . . ? C10 C11 H11A 110(3) . . ? C12 C11 H11B 113(3) . . ? C10 C11 H11B 113(3) . . ? H11A C11 H11B 108(4) . . ? C13 C12 C11 101.8(4) . . ? C13 C12 H12A 111(3) . . ? C11 C12 H12A 116(3) . . ? C13 C12 H12B 105(4) . . ? C11 C12 H12B 111(4) . . ? H12A C12 H12B 110(5) . . ? N C13 C12 104.0(4) . . ? N C13 H13A 114(3) . . ? C12 C13 H13A 114(3) . . ? N C13 H13B 106(3) . . ? C12 C13 H13B 112(3) . . ? H13A C13 H13B 106(4) . . ? C15 C14 C6 113.9(4) . . ? C15 C14 H14A 114(3) . . ? C6 C14 H14A 112(3) . . ? C15 C14 H14B 106(3) . . ? C6 C14 H14B 104(3) . . ? H14A C14 H14B 106(4) . . ? C14 C15 C16 111.9(4) . . ? C14 C15 H15B 104(3) . . ? C16 C15 H15B 112(3) . . ? C14 C15 H15A 103(3) . . ? C16 C15 H15A 118(3) . . ? H15B C15 H15A 106(4) . . ? C15 C16 H16A 109.5 . . ? C15 C16 H16B 109.5 . . ? H16A C16 H16B 109.5 . . ? C15 C16 H16C 109.5 . . ? H16A C16 H16C 109.5 . . ? H16B C16 H16C 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 C13 N C1 O1 -2.0(6) . . . . ? C10 N C1 O1 179.9(4) . . . . ? C13 N C1 C2 178.9(4) . . . . ? C10 N C1 C2 0.8(7) . . . . ? O1 C1 C2 C3 -119.4(5) . . . . ? N C1 C2 C3 59.6(6) . . . . ? C1 C2 C3 C4 -77.5(5) . . . . ? C2 C3 C4 C5 66.0(6) . . . . ? C3 C4 C5 C10 -61.9(5) . . . . ? C3 C4 C5 C6 177.0(4) . . . . ? C4 C5 C6 C7 61.8(5) . . . . ? C10 C5 C6 C7 -64.6(5) . . . . ? C4 C5 C6 C14 -64.7(5) . . . . ? C10 C5 C6 C14 169.0(4) . . . . ? C14 C6 C7 O2 7.8(7) . . . . ? C5 C6 C7 O2 -120.1(5) . . . . ? C14 C6 C7 C8 -172.9(4) . . . . ? C5 C6 C7 C8 59.1(5) . . . . ? O2 C7 C8 C9 130.0(5) . . . . ? C6 C7 C8 C9 -49.3(6) . . . . ? C7 C8 C9 C10 44.4(6) . . . . ? C1 N C10 C9 69.6(6) . . . . ? C13 N C10 C9 -108.6(5) . . . . ? C1 N C10 C5 -55.8(6) . . . . ? C13 N C10 C5 126.0(4) . . . . ? C1 N C10 C11 -172.6(4) . . . . ? C13 N C10 C11 9.2(5) . . . . ? C8 C9 C10 N -179.1(4) . . . . ? C8 C9 C10 C5 -52.2(6) . . . . ? C8 C9 C10 C11 70.2(5) . . . . ? C4 C5 C10 N 66.9(5) . . . . ? C6 C5 C10 N -171.8(4) . . . . ? C4 C5 C10 C9 -58.6(5) . . . . ? C6 C5 C10 C9 62.7(5) . . . . ? C4 C5 C10 C11 178.0(4) . . . . ? C6 C5 C10 C11 -60.7(5) . . . . ? N C10 C11 C12 -30.5(5) . . . . ? C9 C10 C11 C12 86.9(5) . . . . ? C5 C10 C11 C12 -150.1(4) . . . . ? C10 C11 C12 C13 40.6(5) . . . . ? C1 N C13 C12 -163.0(4) . . . . ? C10 N C13 C12 15.4(5) . . . . ? C11 C12 C13 N -33.7(5) . . . . ? C7 C6 C14 C15 171.4(4) . . . . ? C5 C6 C14 C15 -65.3(5) . . . . ? C6 C14 C15 C16 178.2(4) . . . . ? _diffrn_measured_fraction_theta_max 0.943 _diffrn_reflns_theta_full 66.00 _diffrn_measured_fraction_theta_full 0.965 _refine_diff_density_max 0.509 _refine_diff_density_min -0.484 _refine_diff_density_rms 0.098