data_yl_106s _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C17 H21 N O2' _chemical_formula_sum 'C17 H21 N O2' _chemical_formula_weight 271.35 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 Orthorhombic _symmetry_space_group_name_H-M P2(1)2(1)2(1) _chemical_absolute_configuration AD 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 7.1902(3) _cell_length_b 11.3975(4) _cell_length_c 18.3499(6) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 1503.78(10) _cell_formula_units_Z 4 _cell_measurement_temperature 173(2) _cell_measurement_reflns_used 2358 _cell_measurement_theta_min 3.88 _cell_measurement_theta_max 64.58 _exptl_crystal_description irreg _exptl_crystal_colour colourless _exptl_crystal_size_max 0.43 _exptl_crystal_size_mid 0.18 _exptl_crystal_size_min 0.12 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.199 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 584 _exptl_absorpt_coefficient_mu 0.618 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.7770 _exptl_absorpt_correction_T_max 0.9295 _exptl_absorpt_process_details SADABS _exptl_special_details ; ? ; _diffrn_ambient_temperature 173(2) _diffrn_radiation_wavelength 1.54178 _diffrn_radiation_type CuK\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_reflns_number 8918 _diffrn_reflns_av_R_equivalents 0.0214 _diffrn_reflns_av_sigmaI/netI 0.0202 _diffrn_reflns_limit_h_min -8 _diffrn_reflns_limit_h_max 7 _diffrn_reflns_limit_k_min -13 _diffrn_reflns_limit_k_max 11 _diffrn_reflns_limit_l_min -21 _diffrn_reflns_limit_l_max 21 _diffrn_reflns_theta_min 4.57 _diffrn_reflns_theta_max 65.95 _reflns_number_total 2474 _reflns_number_gt 2330 _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, 2008)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _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^)+(0.0970P)^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_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _refine_ls_abs_structure_Flack 0.0(3) _refine_ls_number_reflns 2474 _refine_ls_number_parameters 181 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0377 _refine_ls_R_factor_gt 0.0353 _refine_ls_wR_factor_ref 0.1172 _refine_ls_wR_factor_gt 0.1136 _refine_ls_goodness_of_fit_ref 1.027 _refine_ls_restrained_S_all 1.027 _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 C1 C -1.0383(2) -0.37813(17) -0.49341(9) 0.0381(4) Uani 1 1 d . . . C2 C -1.0439(3) -0.45841(18) -0.55090(8) 0.0430(4) Uani 1 1 d . . . H2A H -1.0494 -0.4326 -0.6001 0.052 Uiso 1 1 calc R . . C3 C -1.0413(3) -0.57575(17) -0.53418(9) 0.0421(4) Uani 1 1 d . . . H3A H -1.0453 -0.6313 -0.5728 0.051 Uiso 1 1 calc R . . C4 C -1.0331(2) -0.61695(16) -0.46156(8) 0.0385(4) Uani 1 1 d . . . C5 C -1.0286(2) -0.53622(16) -0.40518(8) 0.0368(4) Uani 1 1 d . . . H5A H -1.0245 -0.5630 -0.3562 0.044 Uiso 1 1 calc R . . C6 C -1.0299(2) -0.41475(15) -0.41966(8) 0.0349(4) Uani 1 1 d . . . C7 C -1.0243(2) -0.30989(16) -0.37626(10) 0.0398(4) Uani 1 1 d . . . C8 C -1.0305(2) -0.21689(17) -0.42375(10) 0.0439(4) Uani 1 1 d . . . C9 C -1.0202(2) -0.30042(18) -0.29385(10) 0.0447(4) Uani 1 1 d . . . H9A H -0.9950 -0.2168 -0.2806 0.054 Uiso 1 1 calc R . . C10 C -0.8701(3) -0.37545(17) -0.26109(9) 0.0438(4) Uani 1 1 d . . . H10A H -0.8881 -0.4578 -0.2650 0.053 Uiso 1 1 calc R . . C11 C -0.7153(3) -0.34167(16) -0.22728(8) 0.0410(4) Uani 1 1 d . . . H11A H -0.6389 -0.4011 -0.2068 0.049 Uiso 1 1 calc R . . C12 C -0.6538(2) -0.21978(17) -0.21930(8) 0.0385(4) Uani 1 1 d . . . C13 C -0.4731(3) -0.0936(2) -0.14553(13) 0.0605(6) Uani 1 1 d . . . H13A H -0.3945 -0.0961 -0.1019 0.091 Uiso 1 1 calc R . . H13B H -0.5772 -0.0398 -0.1373 0.091 Uiso 1 1 calc R . . H13C H -0.3994 -0.0662 -0.1871 0.091 Uiso 1 1 calc R . . C14 C -1.0415(3) -0.18616(19) -0.56000(12) 0.0544(5) Uani 1 1 d . . . H14A H -1.0503 -0.2373 -0.6028 0.082 Uiso 1 1 calc R . . H14B H -0.9266 -0.1402 -0.5626 0.082 Uiso 1 1 calc R . . H14C H -1.1487 -0.1330 -0.5589 0.082 Uiso 1 1 calc R . . C15 C -1.0307(3) -0.74690(17) -0.44714(10) 0.0487(4) Uani 1 1 d . . . H15A H -1.0249 -0.7608 -0.3945 0.073 Uiso 1 1 calc R . . H15B H -0.9216 -0.7820 -0.4706 0.073 Uiso 1 1 calc R . . H15C H -1.1439 -0.7826 -0.4669 0.073 Uiso 1 1 calc R . . C16 C -1.0299(3) -0.08776(18) -0.40836(15) 0.0594(5) Uani 1 1 d . . . H16A H -1.0215 -0.0749 -0.3557 0.089 Uiso 1 1 calc R . . H16B H -1.1449 -0.0526 -0.4269 0.089 Uiso 1 1 calc R . . H16C H -0.9228 -0.0513 -0.4324 0.089 Uiso 1 1 calc R . . C17 C -1.2085(3) -0.3361(3) -0.26058(11) 0.0709(7) Uani 1 1 d . . . H17A H -1.2026 -0.3285 -0.2074 0.106 Uiso 1 1 calc R . . H17B H -1.2362 -0.4177 -0.2735 0.106 Uiso 1 1 calc R . . H17C H -1.3065 -0.2849 -0.2796 0.106 Uiso 1 1 calc R . . N1 N -1.0402(2) -0.25745(15) -0.49427(9) 0.0438(4) Uani 1 1 d . . . O1 O -0.6926(2) -0.13928(14) -0.25848(8) 0.0652(4) Uani 1 1 d . . . O2 O -0.54354(17) -0.20897(11) -0.16053(6) 0.0435(3) Uani 1 1 d . . . 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 C1 0.0293(7) 0.0420(10) 0.0430(8) 0.0041(7) 0.0015(7) -0.0004(8) C2 0.0405(8) 0.0556(11) 0.0328(7) 0.0026(7) 0.0012(7) 0.0006(9) C3 0.0421(8) 0.0487(10) 0.0356(7) -0.0077(7) 0.0026(7) 0.0014(9) C4 0.0341(7) 0.0422(10) 0.0392(8) -0.0041(7) 0.0025(7) 0.0011(8) C5 0.0333(7) 0.0435(10) 0.0336(7) 0.0001(6) 0.0014(6) 0.0024(8) C6 0.0270(6) 0.0398(9) 0.0380(7) -0.0029(6) 0.0010(7) 0.0017(7) C7 0.0310(7) 0.0397(10) 0.0486(9) -0.0060(7) 0.0006(6) 0.0004(8) C8 0.0307(7) 0.0398(10) 0.0612(10) -0.0039(8) 0.0004(8) 0.0029(8) C9 0.0379(8) 0.0482(11) 0.0479(9) -0.0173(8) -0.0002(7) -0.0020(8) C10 0.0578(10) 0.0367(9) 0.0369(7) -0.0054(7) 0.0018(7) -0.0056(8) C11 0.0497(9) 0.0374(10) 0.0359(7) -0.0027(6) -0.0031(7) 0.0052(8) C12 0.0370(7) 0.0432(10) 0.0354(7) 0.0038(7) -0.0011(6) -0.0015(7) C13 0.0602(11) 0.0460(12) 0.0754(12) 0.0025(9) -0.0215(11) -0.0141(11) C14 0.0451(9) 0.0532(12) 0.0648(11) 0.0202(9) 0.0018(9) 0.0026(10) C15 0.0570(10) 0.0413(10) 0.0477(9) -0.0060(7) 0.0028(8) 0.0016(9) C16 0.0464(9) 0.0384(11) 0.0935(15) -0.0023(10) 0.0032(11) 0.0035(9) C17 0.0484(10) 0.115(2) 0.0498(9) -0.0269(12) 0.0098(9) -0.0115(12) N1 0.0383(7) 0.0412(9) 0.0519(8) 0.0073(6) 0.0037(7) 0.0001(7) O1 0.0810(10) 0.0493(9) 0.0653(8) 0.0191(7) -0.0289(8) -0.0158(8) O2 0.0486(6) 0.0387(7) 0.0431(6) 0.0007(5) -0.0081(5) -0.0036(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 C1 N1 1.376(2) . ? C1 C2 1.397(2) . ? C1 C6 1.417(2) . ? C2 C3 1.372(3) . ? C3 C4 1.414(2) . ? C4 C5 1.385(2) . ? C4 C15 1.505(3) . ? C5 C6 1.410(2) . ? C6 C7 1.437(2) . ? C7 C8 1.373(3) . ? C7 C9 1.516(2) . ? C8 N1 1.376(2) . ? C8 C16 1.499(3) . ? C9 C10 1.502(3) . ? C9 C17 1.540(3) . ? C10 C11 1.331(3) . ? C11 C12 1.465(3) . ? C12 O1 1.199(2) . ? C12 O2 1.344(2) . ? C13 O2 1.435(2) . ? C14 N1 1.454(2) . ? 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 N1 C1 C2 130.23(16) . . ? N1 C1 C6 107.81(16) . . ? C2 C1 C6 121.96(17) . . ? C3 C2 C1 117.97(15) . . ? C2 C3 C4 122.34(15) . . ? C5 C4 C3 118.97(16) . . ? C5 C4 C15 121.49(15) . . ? C3 C4 C15 119.54(15) . . ? C4 C5 C6 120.77(15) . . ? C5 C6 C1 117.99(15) . . ? C5 C6 C7 135.42(15) . . ? C1 C6 C7 106.58(16) . . ? C8 C7 C6 106.83(15) . . ? C8 C7 C9 125.35(17) . . ? C6 C7 C9 127.77(17) . . ? C7 C8 N1 109.83(16) . . ? C7 C8 C16 129.68(18) . . ? N1 C8 C16 120.48(18) . . ? C10 C9 C7 111.88(15) . . ? C10 C9 C17 108.81(18) . . ? C7 C9 C17 111.05(15) . . ? C11 C10 C9 128.49(17) . . ? C10 C11 C12 124.99(16) . . ? O1 C12 O2 123.26(17) . . ? O1 C12 C11 126.54(15) . . ? O2 C12 C11 110.20(14) . . ? C1 N1 C8 108.94(15) . . ? C1 N1 C14 124.63(17) . . ? C8 N1 C14 126.35(17) . . ? C12 O2 C13 116.48(15) . . ? 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 N1 C1 C2 C3 -179.62(19) . . . . ? C6 C1 C2 C3 0.1(3) . . . . ? C1 C2 C3 C4 -0.1(3) . . . . ? C2 C3 C4 C5 0.4(3) . . . . ? C2 C3 C4 C15 -179.99(18) . . . . ? C3 C4 C5 C6 -0.8(3) . . . . ? C15 C4 C5 C6 179.66(16) . . . . ? C4 C5 C6 C1 0.8(2) . . . . ? C4 C5 C6 C7 -179.12(18) . . . . ? N1 C1 C6 C5 179.35(14) . . . . ? C2 C1 C6 C5 -0.4(2) . . . . ? N1 C1 C6 C7 -0.75(19) . . . . ? C2 C1 C6 C7 179.49(15) . . . . ? C5 C6 C7 C8 -179.78(18) . . . . ? C1 C6 C7 C8 0.34(17) . . . . ? C5 C6 C7 C9 -2.0(3) . . . . ? C1 C6 C7 C9 178.12(15) . . . . ? C6 C7 C8 N1 0.20(18) . . . . ? C9 C7 C8 N1 -177.65(15) . . . . ? C6 C7 C8 C16 179.50(18) . . . . ? C9 C7 C8 C16 1.7(3) . . . . ? C8 C7 C9 C10 -131.44(18) . . . . ? C6 C7 C9 C10 51.2(2) . . . . ? C8 C7 C9 C17 106.8(2) . . . . ? C6 C7 C9 C17 -70.6(3) . . . . ? C7 C9 C10 C11 111.8(2) . . . . ? C17 C9 C10 C11 -125.1(2) . . . . ? C9 C10 C11 C12 -4.2(3) . . . . ? C10 C11 C12 O1 -25.5(3) . . . . ? C10 C11 C12 O2 154.77(16) . . . . ? C2 C1 N1 C8 -179.37(17) . . . . ? C6 C1 N1 C8 0.9(2) . . . . ? C2 C1 N1 C14 -2.6(3) . . . . ? C6 C1 N1 C14 177.70(15) . . . . ? C7 C8 N1 C1 -0.7(2) . . . . ? C16 C8 N1 C1 179.94(16) . . . . ? C7 C8 N1 C14 -177.43(16) . . . . ? C16 C8 N1 C14 3.2(3) . . . . ? O1 C12 O2 C13 0.6(3) . . . . ? C11 C12 O2 C13 -179.69(16) . . . . ? _diffrn_measured_fraction_theta_max 0.965 _diffrn_reflns_theta_full 65.95 _diffrn_measured_fraction_theta_full 0.965 _refine_diff_density_max 0.155 _refine_diff_density_min -0.137 _refine_diff_density_rms 0.031