data_09031a _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common 09032a _chemical_melting_point ? _chemical_formula_moiety 'C16 H19 N O2' _chemical_formula_sum 'C16 H19 N O2' _chemical_formula_weight 257.32 _chemical_absolute_configuration rm 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 'Orthorhombic' _symmetry_space_group_name_H-M 'P2(1)2(1)2(1)' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, -y, z+1/2' '-x, y+1/2, -z+1/2' 'x+1/2, -y+1/2, -z' _cell_length_a 7.6848(17) _cell_length_b 10.090(2) _cell_length_c 17.842(4) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 1383.5(5) _cell_formula_units_Z 4 _cell_measurement_temperature 173(2) _cell_measurement_reflns_used 2922 _cell_measurement_theta_min 2.32 _cell_measurement_theta_max 27.39 _exptl_crystal_description 'Block' _exptl_crystal_colour 'Colorless' _exptl_crystal_size_max 0.40 _exptl_crystal_size_mid 0.35 _exptl_crystal_size_min 0.30 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.235 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 552 _exptl_absorpt_coefficient_mu 0.081 _exptl_absorpt_correction_type Multi-scan _exptl_absorpt_correction_T_min 0.9683 _exptl_absorpt_correction_T_max 0.9761 _exptl_absorpt_process_details 'SADABS (sHELDRICK, 2008)' _exptl_special_details 'R. Hayashi / Prof. R. Hsung - U. Wisconsin' _diffrn_ambient_temperature 173(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source '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 16532 _diffrn_reflns_av_R_equivalents 0.0327 _diffrn_reflns_av_sigmaI/netI 0.0162 _diffrn_reflns_limit_h_min 0 _diffrn_reflns_limit_h_max 9 _diffrn_reflns_limit_k_min 0 _diffrn_reflns_limit_k_max 13 _diffrn_reflns_limit_l_min 0 _diffrn_reflns_limit_l_max 23 _diffrn_reflns_theta_min 2.28 _diffrn_reflns_theta_max 27.51 _reflns_number_total 1834 _reflns_number_gt 1662 _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^)+(0.0445P)^2^+0.2475P] 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_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _refine_ls_abs_structure_Flack 0.5(14) _refine_ls_number_reflns 1834 _refine_ls_number_parameters 174 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0357 _refine_ls_R_factor_gt 0.0297 _refine_ls_wR_factor_ref 0.0840 _refine_ls_wR_factor_gt 0.0784 _refine_ls_goodness_of_fit_ref 1.057 _refine_ls_restrained_S_all 1.057 _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 0.69011(16) 0.21133(12) 0.33106(6) 0.0348(3) Uani 1 1 d . . . O2 O 0.58331(16) 0.01664(12) 0.29091(6) 0.0305(3) Uani 1 1 d . . . N1 N 0.41707(19) 0.13632(13) 0.36640(7) 0.0272(3) Uani 1 1 d . . . C1 C 0.5737(2) 0.13202(16) 0.33072(8) 0.0271(3) Uani 1 1 d . . . C2 C 0.4344(2) -0.06536(17) 0.30896(10) 0.0302(4) Uani 1 1 d . . . H2A H 0.4663 -0.1343 0.3460 0.036 Uiso 1 1 calc R . . H2B H 0.3885 -0.1092 0.2634 0.036 Uiso 1 1 calc R . . C3 C 0.3007(2) 0.02961(15) 0.34158(8) 0.0257(3) Uani 1 1 d . . . H3A H 0.2445 -0.0121 0.3863 0.031 Uiso 1 1 calc R . . C4 C 0.1594(2) 0.07630(17) 0.28687(10) 0.0322(4) Uani 1 1 d . . . H4A H 0.0846 0.1422 0.3136 0.039 Uiso 1 1 calc R . . C5 C 0.0451(2) -0.0412(2) 0.26491(12) 0.0411(4) Uani 1 1 d . . . H5A H 0.0039 -0.0861 0.3103 0.062 Uiso 1 1 calc R . . H5B H 0.1130 -0.1033 0.2345 0.062 Uiso 1 1 calc R . . H5C H -0.0549 -0.0095 0.2359 0.062 Uiso 1 1 calc R . . C6 C 0.2346(3) 0.1440(2) 0.21737(11) 0.0446(5) Uani 1 1 d . . . H6A H 0.2976 0.2241 0.2324 0.067 Uiso 1 1 calc R . . H6B H 0.1398 0.1680 0.1832 0.067 Uiso 1 1 calc R . . H6C H 0.3146 0.0832 0.1919 0.067 Uiso 1 1 calc R . . C7 C 0.3620(2) 0.23926(16) 0.41604(8) 0.0265(3) Uani 1 1 d . . . C8 C 0.2991(3) 0.19391(16) 0.48930(9) 0.0314(4) Uani 1 1 d . . . H8A H 0.2193 0.2495 0.5151 0.038 Uiso 1 1 calc R . . C9 C 0.3447(3) 0.08153(18) 0.52229(10) 0.0399(4) Uani 1 1 d . . . H9A H 0.4242 0.0232 0.4983 0.048 Uiso 1 1 calc R . . H9B H 0.2980 0.0593 0.5700 0.048 Uiso 1 1 calc R . . C10 C 0.3681(2) 0.36557(17) 0.39335(9) 0.0293(3) Uani 1 1 d . . . H10A H 0.4072 0.3799 0.3435 0.035 Uiso 1 1 calc R . . C11 C 0.3216(2) 0.48474(16) 0.43611(9) 0.0275(3) Uani 1 1 d . . . C12 C 0.3374(2) 0.49587(16) 0.51415(9) 0.0305(4) Uani 1 1 d . . . H12A H 0.3898 0.4263 0.5420 0.037 Uiso 1 1 calc R . . C13 C 0.2769(2) 0.60785(17) 0.55091(10) 0.0347(4) Uani 1 1 d . . . H13A H 0.2874 0.6138 0.6039 0.042 Uiso 1 1 calc R . . C14 C 0.2017(3) 0.71084(17) 0.51153(11) 0.0382(4) Uani 1 1 d . . . H14A H 0.1571 0.7860 0.5372 0.046 Uiso 1 1 calc R . . C15 C 0.1921(3) 0.70324(17) 0.43436(11) 0.0384(4) Uani 1 1 d . . . H15A H 0.1427 0.7745 0.4068 0.046 Uiso 1 1 calc R . . C16 C 0.2537(2) 0.59288(16) 0.39694(10) 0.0331(4) Uani 1 1 d . . . H16A H 0.2497 0.5905 0.3437 0.040 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 0.0308(6) 0.0386(6) 0.0351(6) -0.0001(5) 0.0045(5) -0.0056(6) O2 0.0302(6) 0.0319(6) 0.0293(5) -0.0055(5) 0.0043(5) 0.0037(5) N1 0.0306(7) 0.0245(6) 0.0265(6) -0.0030(5) 0.0067(6) -0.0022(6) C1 0.0303(8) 0.0301(8) 0.0210(7) 0.0018(6) 0.0009(6) 0.0039(7) C2 0.0295(8) 0.0277(8) 0.0334(8) -0.0042(7) -0.0004(7) 0.0028(7) C3 0.0302(8) 0.0227(7) 0.0241(7) -0.0001(6) 0.0041(6) 0.0004(7) C4 0.0289(8) 0.0298(8) 0.0379(9) 0.0021(7) 0.0010(7) 0.0042(7) C5 0.0318(9) 0.0444(10) 0.0472(11) 0.0068(9) -0.0065(8) -0.0042(8) C6 0.0461(11) 0.0443(10) 0.0433(10) 0.0159(9) -0.0106(9) -0.0067(9) C7 0.0285(8) 0.0279(8) 0.0230(7) -0.0034(6) 0.0027(6) 0.0013(7) C8 0.0381(9) 0.0293(8) 0.0266(7) -0.0031(6) 0.0080(7) -0.0009(7) C9 0.0538(12) 0.0394(9) 0.0267(8) 0.0027(8) 0.0060(9) 0.0014(9) C10 0.0358(9) 0.0291(8) 0.0230(7) -0.0020(6) 0.0032(7) -0.0015(7) C11 0.0290(8) 0.0256(7) 0.0280(7) -0.0012(6) 0.0012(6) -0.0028(7) C12 0.0325(8) 0.0297(8) 0.0293(8) -0.0004(7) -0.0015(7) -0.0003(7) C13 0.0367(9) 0.0373(9) 0.0302(8) -0.0092(7) 0.0016(7) -0.0055(8) C14 0.0373(9) 0.0279(8) 0.0493(10) -0.0091(8) 0.0055(9) -0.0019(8) C15 0.0418(10) 0.0236(8) 0.0497(10) 0.0032(8) -0.0034(9) -0.0008(8) C16 0.0412(9) 0.0271(8) 0.0309(8) 0.0025(6) -0.0016(8) -0.0053(8) _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 1.200(2) . ? O2 C1 1.3658(19) . ? O2 C2 1.448(2) . ? N1 C1 1.363(2) . ? N1 C7 1.429(2) . ? N1 C3 1.468(2) . ? C2 C3 1.521(2) . ? C2 H2A 0.9900 . ? C2 H2B 0.9900 . ? C3 C4 1.534(2) . ? C3 H3A 1.0000 . ? C4 C5 1.526(3) . ? C4 C6 1.529(3) . ? C4 H4A 1.0000 . ? C5 H5A 0.9800 . ? C5 H5B 0.9800 . ? C5 H5C 0.9800 . ? C6 H6A 0.9800 . ? C6 H6B 0.9800 . ? C6 H6C 0.9800 . ? C7 C10 1.338(2) . ? C7 C8 1.467(2) . ? C8 C9 1.325(2) . ? C8 H8A 0.9500 . ? C9 H9A 0.9500 . ? C9 H9B 0.9500 . ? C10 C11 1.468(2) . ? C10 H10A 0.9500 . ? C11 C16 1.397(2) . ? C11 C12 1.402(2) . ? C12 C13 1.387(2) . ? C12 H12A 0.9500 . ? C13 C14 1.381(3) . ? C13 H13A 0.9500 . ? C14 C15 1.381(3) . ? C14 H14A 0.9500 . ? C15 C16 1.382(2) . ? C15 H15A 0.9500 . ? C16 H16A 0.9500 . ? 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 O2 C2 109.19(12) . . ? C1 N1 C7 125.06(14) . . ? C1 N1 C3 111.97(13) . . ? C7 N1 C3 122.64(13) . . ? O1 C1 N1 129.41(15) . . ? O1 C1 O2 122.07(15) . . ? N1 C1 O2 108.52(14) . . ? O2 C2 C3 105.02(12) . . ? O2 C2 H2A 110.7 . . ? C3 C2 H2A 110.7 . . ? O2 C2 H2B 110.7 . . ? C3 C2 H2B 110.7 . . ? H2A C2 H2B 108.8 . . ? N1 C3 C2 99.53(13) . . ? N1 C3 C4 113.45(13) . . ? C2 C3 C4 115.36(13) . . ? N1 C3 H3A 109.4 . . ? C2 C3 H3A 109.4 . . ? C4 C3 H3A 109.4 . . ? C5 C4 C6 110.86(15) . . ? C5 C4 C3 109.39(14) . . ? C6 C4 C3 112.70(15) . . ? C5 C4 H4A 107.9 . . ? C6 C4 H4A 107.9 . . ? C3 C4 H4A 107.9 . . ? C4 C5 H5A 109.5 . . ? C4 C5 H5B 109.5 . . ? H5A C5 H5B 109.5 . . ? C4 C5 H5C 109.5 . . ? H5A C5 H5C 109.5 . . ? H5B C5 H5C 109.5 . . ? C4 C6 H6A 109.5 . . ? C4 C6 H6B 109.5 . . ? H6A C6 H6B 109.5 . . ? C4 C6 H6C 109.5 . . ? H6A C6 H6C 109.5 . . ? H6B C6 H6C 109.5 . . ? C10 C7 N1 119.63(14) . . ? C10 C7 C8 125.32(14) . . ? N1 C7 C8 115.03(14) . . ? C9 C8 C7 125.14(17) . . ? C9 C8 H8A 117.4 . . ? C7 C8 H8A 117.4 . . ? C8 C9 H9A 120.0 . . ? C8 C9 H9B 120.0 . . ? H9A C9 H9B 120.0 . . ? C7 C10 C11 127.91(15) . . ? C7 C10 H10A 116.0 . . ? C11 C10 H10A 116.0 . . ? C16 C11 C12 117.81(16) . . ? C16 C11 C10 118.07(14) . . ? C12 C11 C10 124.10(15) . . ? C13 C12 C11 120.40(16) . . ? C13 C12 H12A 119.8 . . ? C11 C12 H12A 119.8 . . ? C14 C13 C12 120.84(16) . . ? C14 C13 H13A 119.6 . . ? C12 C13 H13A 119.6 . . ? C15 C14 C13 119.20(17) . . ? C15 C14 H14A 120.4 . . ? C13 C14 H14A 120.4 . . ? C14 C15 C16 120.53(18) . . ? C14 C15 H15A 119.7 . . ? C16 C15 H15A 119.7 . . ? C15 C16 C11 121.05(16) . . ? C15 C16 H16A 119.5 . . ? C11 C16 H16A 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 C7 N1 C1 O1 -2.8(3) . . . . ? C3 N1 C1 O1 170.69(16) . . . . ? C7 N1 C1 O2 177.28(13) . . . . ? C3 N1 C1 O2 -9.21(17) . . . . ? C2 O2 C1 O1 172.79(15) . . . . ? C2 O2 C1 N1 -7.29(16) . . . . ? C1 O2 C2 C3 19.92(16) . . . . ? C1 N1 C3 C2 20.28(16) . . . . ? C7 N1 C3 C2 -166.03(14) . . . . ? C1 N1 C3 C4 -102.82(16) . . . . ? C7 N1 C3 C4 70.87(18) . . . . ? O2 C2 C3 N1 -23.10(15) . . . . ? O2 C2 C3 C4 98.64(15) . . . . ? N1 C3 C4 C5 -179.65(14) . . . . ? C2 C3 C4 C5 66.44(18) . . . . ? N1 C3 C4 C6 56.55(19) . . . . ? C2 C3 C4 C6 -57.4(2) . . . . ? C1 N1 C7 C10 53.2(2) . . . . ? C3 N1 C7 C10 -119.63(18) . . . . ? C1 N1 C7 C8 -127.80(17) . . . . ? C3 N1 C7 C8 59.4(2) . . . . ? C10 C7 C8 C9 -155.6(2) . . . . ? N1 C7 C8 C9 25.5(3) . . . . ? N1 C7 C10 C11 -178.44(16) . . . . ? C8 C7 C10 C11 2.7(3) . . . . ? C7 C10 C11 C16 -148.41(19) . . . . ? C7 C10 C11 C12 30.0(3) . . . . ? C16 C11 C12 C13 3.9(3) . . . . ? C10 C11 C12 C13 -174.53(16) . . . . ? C11 C12 C13 C14 -0.6(3) . . . . ? C12 C13 C14 C15 -2.1(3) . . . . ? C13 C14 C15 C16 1.3(3) . . . . ? C14 C15 C16 C11 2.2(3) . . . . ? C12 C11 C16 C15 -4.7(3) . . . . ? C10 C11 C16 C15 173.84(17) . . . . ? _diffrn_measured_fraction_theta_max 0.998 _diffrn_reflns_theta_full 27.51 _diffrn_measured_fraction_theta_full 0.998 _refine_diff_density_max 0.173 _refine_diff_density_min -0.153 _refine_diff_density_rms 0.029