data_z _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C16 H19 N O2' _chemical_formula_weight 257.32 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 7.1402(2) _cell_length_b 12.5429(3) _cell_length_c 15.2299(3) _cell_angle_alpha 90.00 _cell_angle_beta 101.1040(10) _cell_angle_gamma 90.00 _cell_volume 1338.44(6) _cell_formula_units_Z 4 _cell_measurement_temperature 296(2) _cell_measurement_reflns_used 6019 _cell_measurement_theta_min 2.73 _cell_measurement_theta_max 29.98 _exptl_crystal_description block _exptl_crystal_colour ? _exptl_crystal_size_max 0.725 _exptl_crystal_size_mid 0.593 _exptl_crystal_size_min 0.434 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.277 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 552 _exptl_absorpt_coefficient_mu 0.084 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.897748 _exptl_absorpt_correction_T_max 1.000 _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 296(2) _diffrn_radiation_wavelength 0.71073 _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_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 11226 _diffrn_reflns_av_R_equivalents 0.0206 _diffrn_reflns_av_sigmaI/netI 0.0163 _diffrn_reflns_limit_h_min -9 _diffrn_reflns_limit_h_max 9 _diffrn_reflns_limit_k_min -12 _diffrn_reflns_limit_k_max 15 _diffrn_reflns_limit_l_min -16 _diffrn_reflns_limit_l_max 19 _diffrn_reflns_theta_min 2.12 _diffrn_reflns_theta_max 27.00 _reflns_number_total 2919 _reflns_number_gt 2513 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SMART' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _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^)+(0.0551P)^2^+0.2675P] 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 2919 _refine_ls_number_parameters 172 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0452 _refine_ls_R_factor_gt 0.0395 _refine_ls_wR_factor_ref 0.1106 _refine_ls_wR_factor_gt 0.1053 _refine_ls_goodness_of_fit_ref 1.047 _refine_ls_restrained_S_all 1.047 _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 O2 O 0.77973(12) 0.62534(7) -0.06016(6) 0.0466(2) Uani 1 1 d . . . C7 C 1.04090(15) 0.65966(9) 0.05069(7) 0.0345(2) Uani 1 1 d . . . H7A H 1.0795 0.5852 0.0464 0.041 Uiso 1 1 calc R . . N1 N 0.97710(14) 0.86684(8) 0.13944(7) 0.0401(2) Uani 1 1 d . . . C6 C 1.15860(15) 0.70115(9) 0.13721(7) 0.0353(2) Uani 1 1 d . . . C8 C 0.82104(16) 0.65859(9) 0.03271(7) 0.0370(3) Uani 1 1 d . . . C5 C 1.13680(16) 0.80143(9) 0.17404(8) 0.0377(3) Uani 1 1 d . . . C4 C 1.26762(19) 0.83723(12) 0.24820(9) 0.0488(3) Uani 1 1 d . . . H4A H 1.2531 0.9046 0.2715 0.059 Uiso 1 1 calc R . . C10 C 0.78007(16) 0.82570(9) 0.12682(8) 0.0399(3) Uani 1 1 d . . . H10A H 0.7663 0.7790 0.1768 0.048 Uiso 1 1 calc R . . C15 C 1.08070(18) 0.71423(11) -0.03366(8) 0.0443(3) Uani 1 1 d . . . H15A H 1.0813 0.7912 -0.0275 0.053 Uiso 1 1 calc R . . H15B H 1.2019 0.6913 -0.0471 0.053 Uiso 1 1 calc R . . C9 C 0.72356(16) 0.76635(10) 0.03868(8) 0.0423(3) Uani 1 1 d . . . H9A H 0.7512 0.8117 -0.0088 0.051 Uiso 1 1 calc R . . H9B H 0.5867 0.7549 0.0276 0.051 Uiso 1 1 calc R . . C1 C 1.31073(17) 0.63769(11) 0.17959(8) 0.0436(3) Uani 1 1 d . . . H1A H 1.3258 0.5698 0.1574 0.052 Uiso 1 1 calc R . . O1 O 1.13291(16) 1.02427(8) 0.12376(8) 0.0674(3) Uani 1 1 d . . . C2 C 1.43942(18) 0.67324(13) 0.25367(9) 0.0519(3) Uani 1 1 d . . . H2A H 1.5395 0.6296 0.2806 0.062 Uiso 1 1 calc R . . C13 C 0.9864(2) 0.97344(10) 0.12132(9) 0.0484(3) Uani 1 1 d . . . C3 C 1.41837(18) 0.77361(13) 0.28735(9) 0.0548(4) Uani 1 1 d . . . H3A H 1.5057 0.7984 0.3364 0.066 Uiso 1 1 calc R . . C14 C 0.9143(2) 0.67717(12) -0.10555(8) 0.0512(3) Uani 1 1 d . . . H14A H 0.8549 0.7376 -0.1398 0.061 Uiso 1 1 calc R . . H14B H 0.9586 0.6278 -0.1461 0.061 Uiso 1 1 calc R . . C16 C 0.7415(2) 0.57368(11) 0.08588(10) 0.0507(3) Uani 1 1 d . . . H16A H 0.6046 0.5763 0.0724 0.076 Uiso 1 1 calc R . . H16B H 0.7858 0.5861 0.1486 0.076 Uiso 1 1 calc R . . H16C H 0.7837 0.5048 0.0703 0.076 Uiso 1 1 calc R . . C12 C 0.7846(2) 1.01421(11) 0.09620(11) 0.0578(4) Uani 1 1 d . . . H12A H 0.7473 1.0228 0.0319 0.069 Uiso 1 1 calc R . . H12B H 0.7711 1.0821 0.1248 0.069 Uiso 1 1 calc R . . C11 C 0.6647(2) 0.92867(11) 0.12997(10) 0.0536(3) Uani 1 1 d . . . H11A H 0.5398 0.9232 0.0916 0.064 Uiso 1 1 calc R . . H11B H 0.6488 0.9440 0.1905 0.064 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 0.0465(5) 0.0547(5) 0.0356(4) -0.0085(4) 0.0003(4) -0.0021(4) C7 0.0356(5) 0.0357(5) 0.0321(5) -0.0019(4) 0.0061(4) 0.0025(4) N1 0.0412(5) 0.0370(5) 0.0432(5) -0.0050(4) 0.0108(4) -0.0018(4) C6 0.0323(5) 0.0424(6) 0.0313(5) 0.0012(4) 0.0068(4) -0.0014(4) C8 0.0358(6) 0.0405(6) 0.0332(6) -0.0041(4) 0.0035(4) -0.0012(4) C5 0.0357(6) 0.0452(6) 0.0331(6) -0.0027(5) 0.0088(4) -0.0047(5) C4 0.0470(7) 0.0612(8) 0.0391(6) -0.0125(6) 0.0101(5) -0.0121(6) C10 0.0379(6) 0.0392(6) 0.0447(7) -0.0005(5) 0.0132(5) 0.0015(5) C15 0.0473(7) 0.0518(7) 0.0355(6) 0.0003(5) 0.0122(5) -0.0016(5) C9 0.0339(6) 0.0455(6) 0.0457(7) -0.0011(5) 0.0034(5) 0.0041(5) C1 0.0365(6) 0.0527(7) 0.0413(6) 0.0057(5) 0.0067(5) 0.0028(5) O1 0.0707(7) 0.0498(6) 0.0862(8) -0.0001(5) 0.0264(6) -0.0161(5) C2 0.0358(6) 0.0755(9) 0.0423(7) 0.0113(6) 0.0022(5) 0.0004(6) C13 0.0601(8) 0.0402(6) 0.0494(7) -0.0042(5) 0.0217(6) -0.0028(6) C3 0.0400(7) 0.0858(10) 0.0363(6) -0.0034(6) 0.0013(5) -0.0153(7) C14 0.0530(7) 0.0673(8) 0.0325(6) 0.0018(6) 0.0058(5) 0.0059(6) C16 0.0535(7) 0.0449(7) 0.0571(8) -0.0037(6) 0.0193(6) -0.0073(6) C12 0.0693(9) 0.0421(7) 0.0683(9) 0.0037(6) 0.0289(7) 0.0112(6) C11 0.0522(7) 0.0466(7) 0.0671(9) -0.0025(6) 0.0239(7) 0.0094(6) _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 C14 1.4421(17) . ? O2 C8 1.4494(14) . ? C7 C6 1.5123(15) . ? C7 C15 1.5297(16) . ? C7 C8 1.5408(15) . ? C7 H7A 0.9800 . ? N1 C13 1.3695(16) . ? N1 C5 1.4212(15) . ? N1 C10 1.4759(15) . ? C6 C1 1.4000(16) . ? C6 C5 1.3981(16) . ? C8 C16 1.5132(17) . ? C8 C9 1.5310(16) . ? C5 C4 1.3940(17) . ? C4 C3 1.380(2) . ? C4 H4A 0.9300 . ? C10 C9 1.5199(17) . ? C10 C11 1.5376(17) . ? C10 H10A 0.9800 . ? C15 C14 1.5249(18) . ? C15 H15A 0.9700 . ? C15 H15B 0.9700 . ? C9 H9A 0.9700 . ? C9 H9B 0.9700 . ? C1 C2 1.3844(18) . ? C1 H1A 0.9300 . ? O1 C13 1.2193(16) . ? C2 C3 1.379(2) . ? C2 H2A 0.9300 . ? C13 C12 1.508(2) . ? C3 H3A 0.9300 . ? C14 H14A 0.9700 . ? C14 H14B 0.9700 . ? C16 H16A 0.9600 . ? C16 H16B 0.9600 . ? C16 H16C 0.9600 . ? C12 C11 1.523(2) . ? C12 H12A 0.9700 . ? C12 H12B 0.9700 . ? C11 H11A 0.9700 . ? C11 H11B 0.9700 . ? 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 O2 C8 107.99(9) . . ? C6 C7 C15 114.58(9) . . ? C6 C7 C8 122.28(9) . . ? C15 C7 C8 101.67(9) . . ? C6 C7 H7A 105.7 . . ? C15 C7 H7A 105.7 . . ? C8 C7 H7A 105.7 . . ? C13 N1 C5 124.87(10) . . ? C13 N1 C10 113.41(10) . . ? C5 N1 C10 121.54(9) . . ? C1 C6 C5 117.58(11) . . ? C1 C6 C7 117.24(10) . . ? C5 C6 C7 124.97(10) . . ? O2 C8 C16 107.03(9) . . ? O2 C8 C9 107.62(9) . . ? C16 C8 C9 111.58(10) . . ? O2 C8 C7 100.65(9) . . ? C16 C8 C7 112.68(10) . . ? C9 C8 C7 116.17(9) . . ? C4 C5 C6 120.39(11) . . ? C4 C5 N1 118.63(11) . . ? C6 C5 N1 120.93(10) . . ? C3 C4 C5 120.60(13) . . ? C3 C4 H4A 119.7 . . ? C5 C4 H4A 119.7 . . ? N1 C10 C9 111.74(9) . . ? N1 C10 C11 101.85(10) . . ? C9 C10 C11 112.73(11) . . ? N1 C10 H10A 110.1 . . ? C9 C10 H10A 110.1 . . ? C11 C10 H10A 110.1 . . ? C14 C15 C7 102.80(10) . . ? C14 C15 H15A 111.2 . . ? C7 C15 H15A 111.2 . . ? C14 C15 H15B 111.2 . . ? C7 C15 H15B 111.2 . . ? H15A C15 H15B 109.1 . . ? C10 C9 C8 116.01(10) . . ? C10 C9 H9A 108.3 . . ? C8 C9 H9A 108.3 . . ? C10 C9 H9B 108.3 . . ? C8 C9 H9B 108.3 . . ? H9A C9 H9B 107.4 . . ? C6 C1 C2 121.80(13) . . ? C6 C1 H1A 119.1 . . ? C2 C1 H1A 119.1 . . ? C3 C2 C1 119.64(13) . . ? C3 C2 H2A 120.2 . . ? C1 C2 H2A 120.2 . . ? O1 C13 N1 125.39(13) . . ? O1 C13 C12 127.07(12) . . ? N1 C13 C12 107.52(11) . . ? C4 C3 C2 119.96(12) . . ? C4 C3 H3A 120.0 . . ? C2 C3 H3A 120.0 . . ? O2 C14 C15 106.98(10) . . ? O2 C14 H14A 110.3 . . ? C15 C14 H14A 110.3 . . ? O2 C14 H14B 110.3 . . ? C15 C14 H14B 110.3 . . ? H14A C14 H14B 108.6 . . ? C8 C16 H16A 109.5 . . ? C8 C16 H16B 109.5 . . ? H16A C16 H16B 109.5 . . ? C8 C16 H16C 109.5 . . ? H16A C16 H16C 109.5 . . ? H16B C16 H16C 109.5 . . ? C13 C12 C11 104.33(11) . . ? C13 C12 H12A 110.9 . . ? C11 C12 H12A 110.9 . . ? C13 C12 H12B 110.9 . . ? C11 C12 H12B 110.9 . . ? H12A C12 H12B 108.9 . . ? C12 C11 C10 104.00(10) . . ? C12 C11 H11A 111.0 . . ? C10 C11 H11A 111.0 . . ? C12 C11 H11B 111.0 . . ? C10 C11 H11B 111.0 . . ? H11A C11 H11B 109.0 . . ? 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 C15 C7 C6 C1 -104.18(12) . . . . ? C8 C7 C6 C1 132.32(11) . . . . ? C15 C7 C6 C5 70.32(14) . . . . ? C8 C7 C6 C5 -53.18(16) . . . . ? C14 O2 C8 C16 -156.94(10) . . . . ? C14 O2 C8 C9 83.00(11) . . . . ? C14 O2 C8 C7 -39.05(11) . . . . ? C6 C7 C8 O2 173.26(9) . . . . ? C15 C7 C8 O2 44.00(10) . . . . ? C6 C7 C8 C16 -73.07(14) . . . . ? C15 C7 C8 C16 157.68(10) . . . . ? C6 C7 C8 C9 57.43(14) . . . . ? C15 C7 C8 C9 -71.82(12) . . . . ? C1 C6 C5 C4 2.44(16) . . . . ? C7 C6 C5 C4 -172.04(11) . . . . ? C1 C6 C5 N1 -174.73(10) . . . . ? C7 C6 C5 N1 10.78(17) . . . . ? C13 N1 C5 C4 48.62(17) . . . . ? C10 N1 C5 C4 -126.09(12) . . . . ? C13 N1 C5 C6 -134.15(12) . . . . ? C10 N1 C5 C6 51.14(15) . . . . ? C6 C5 C4 C3 -1.19(19) . . . . ? N1 C5 C4 C3 176.05(11) . . . . ? C13 N1 C10 C9 101.37(12) . . . . ? C5 N1 C10 C9 -83.36(13) . . . . ? C13 N1 C10 C11 -19.21(13) . . . . ? C5 N1 C10 C11 156.06(11) . . . . ? C6 C7 C15 C14 -166.91(10) . . . . ? C8 C7 C15 C14 -32.96(12) . . . . ? N1 C10 C9 C8 70.48(13) . . . . ? C11 C10 C9 C8 -175.52(10) . . . . ? O2 C8 C9 C10 -168.56(9) . . . . ? C16 C8 C9 C10 74.31(13) . . . . ? C7 C8 C9 C10 -56.71(14) . . . . ? C5 C6 C1 C2 -1.95(17) . . . . ? C7 C6 C1 C2 172.96(11) . . . . ? C6 C1 C2 C3 0.16(19) . . . . ? C5 N1 C13 O1 7.8(2) . . . . ? C10 N1 C13 O1 -177.16(13) . . . . ? C5 N1 C13 C12 -173.52(11) . . . . ? C10 N1 C13 C12 1.57(15) . . . . ? C5 C4 C3 C2 -0.7(2) . . . . ? C1 C2 C3 C4 1.2(2) . . . . ? C8 O2 C14 C15 18.50(13) . . . . ? C7 C15 C14 O2 10.28(13) . . . . ? O1 C13 C12 C11 -164.18(14) . . . . ? N1 C13 C12 C11 17.12(15) . . . . ? C13 C12 C11 C10 -28.18(15) . . . . ? N1 C10 C11 C12 28.33(14) . . . . ? C9 C10 C11 C12 -91.55(13) . . . . ? _diffrn_measured_fraction_theta_max 0.999 _diffrn_reflns_theta_full 27.00 _diffrn_measured_fraction_theta_full 0.999 _refine_diff_density_max 0.225 _refine_diff_density_min -0.200 _refine_diff_density_rms 0.036