_publ_section_references ; Altomare, A., Burla, M. C., Camalli, M., Cascarano, G. L., Giacovazzo, C., Guagliardi, A., Moliterni, A. G. G., Polidori, G., Spagna, R (1999). SIR97, J. Appl. Cryst. 32, 115-119. Bruker (2009). SAINT V7.68A, Bruker AXS, Inc., Madison, WI, USA. Bruker (2010). APEX2 V2010.7-0, Bruker AXS, Inc., Madison, WI, USA. Sheldrick, G. M. (2008). SADABS V2008/1, University of G\"ottingen, Germany. Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122. ; data_frojb05 _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common frojb05 _chemical_melting_point ? _chemical_formula_moiety 'C18 H23 N O2' _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 'C 1 2/c 1' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y, -z+1/2' 'x+1/2, y+1/2, z' '-x+1/2, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y, z-1/2' '-x+1/2, -y+1/2, -z' 'x+1/2, -y+1/2, z-1/2' _cell_length_a 20.782(2) _cell_length_b 6.3342(8) _cell_length_c 24.168(3) _cell_angle_alpha 90.00 _cell_angle_beta 93.654(2) _cell_angle_gamma 90.00 _cell_volume 3175.0(7) _cell_formula_units_Z 8 _cell_measurement_temperature 100.0(1) _cell_measurement_reflns_used 4028 _cell_measurement_theta_min 2.51 _cell_measurement_theta_max 37.42 _exptl_crystal_description block _exptl_crystal_colour colorless _exptl_crystal_size_max 0.42 _exptl_crystal_size_mid 0.20 _exptl_crystal_size_min 0.12 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.194 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1232 _exptl_absorpt_coefficient_mu 0.077 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.9683 _exptl_absorpt_correction_T_max 0.9908 _exptl_absorpt_process_details 'SADABS (Sheldrick, 2008)' _exptl_special_details ; ? ; _diffrn_ambient_temperature 100.0(1) _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 'Bruker SMART APEX II CCD Platform' _diffrn_measurement_method 'area detector, \w scans per \f' _diffrn_detector_area_resol_mean ? _diffrn_standards_number 0 _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 50883 _diffrn_reflns_av_R_equivalents 0.0446 _diffrn_reflns_av_sigmaI/netI 0.0315 _diffrn_reflns_limit_h_min -35 _diffrn_reflns_limit_h_max 35 _diffrn_reflns_limit_k_min -10 _diffrn_reflns_limit_k_max 10 _diffrn_reflns_limit_l_min -41 _diffrn_reflns_limit_l_max 41 _diffrn_reflns_theta_min 1.69 _diffrn_reflns_theta_max 37.78 _reflns_number_total 8422 _reflns_number_gt 6449 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'APEX2 (Bruker, 2010)' _computing_cell_refinement 'SAINT (Bruker, 2009)' _computing_data_reduction 'SAINT (Bruker, 2009)' _computing_structure_solution 'SIR97 (Altomare et al., 1999)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _computing_molecular_graphics 'SHELXTL (Sheldrick, 2008)' _computing_publication_material 'SHELXTL (Sheldrick, 2008)' _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^)+(0.0656P)^2^+0.8847P] 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 refall _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 8422 _refine_ls_number_parameters 282 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0645 _refine_ls_R_factor_gt 0.0455 _refine_ls_wR_factor_ref 0.1267 _refine_ls_wR_factor_gt 0.1157 _refine_ls_goodness_of_fit_ref 1.034 _refine_ls_restrained_S_all 1.034 _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 0.42706(2) 0.17924(8) 0.49652(2) 0.01559(9) Uani 1 1 d . . . H1A H 0.4562(7) 0.204(2) 0.4717(6) 0.034(3) Uiso 1 1 d . . . N1 N 0.47011(3) 0.81284(9) 0.56809(2) 0.01397(10) Uani 1 1 d . . . H1B H 0.4507(5) 0.9221(19) 0.5494(5) 0.022(3) Uiso 1 1 d . . . C1 C 0.38085(3) 0.34092(10) 0.49814(3) 0.01283(10) Uani 1 1 d . . . O2 O 0.31834(3) 0.21756(9) 0.41482(3) 0.02216(11) Uani 1 1 d . . . C2 C 0.33658(3) 0.36248(11) 0.44492(3) 0.01449(11) Uani 1 1 d . . . C3 C 0.31899(3) 0.58753(11) 0.43909(3) 0.01497(11) Uani 1 1 d . . . C4 C 0.35941(3) 0.69984(11) 0.47342(3) 0.01509(11) Uani 1 1 d . . . H4 H 0.3579(5) 0.8496(18) 0.4778(5) 0.019(3) Uiso 1 1 d . . . C5 C 0.40909(3) 0.56608(10) 0.50539(3) 0.01274(10) Uani 1 1 d . . . H5 H 0.4498(5) 0.5700(17) 0.4857(4) 0.016(2) Uiso 1 1 d . . . C6 C 0.33691(3) 0.27924(11) 0.54407(3) 0.01764(12) Uani 1 1 d . . . H6A H 0.3021(6) 0.3850(19) 0.5489(5) 0.024(3) Uiso 1 1 d . . . H6B H 0.3148(6) 0.142(2) 0.5342(5) 0.029(3) Uiso 1 1 d . . . H6C H 0.3635(6) 0.2619(19) 0.5799(5) 0.025(3) Uiso 1 1 d . . . C7 C 0.42570(3) 0.63289(11) 0.56527(3) 0.01517(11) Uani 1 1 d . . . H7A H 0.3867(5) 0.6614(17) 0.5847(4) 0.017(2) Uiso 1 1 d . . . H7B H 0.4477(5) 0.5138(17) 0.5854(4) 0.015(2) Uiso 1 1 d . . . C8 C 0.48646(4) 0.88005(12) 0.62553(3) 0.01952(13) Uani 1 1 d . . . H8A H 0.4471(6) 0.925(2) 0.6439(5) 0.028(3) Uiso 1 1 d . . . H8B H 0.5040(6) 0.752(2) 0.6452(5) 0.028(3) Uiso 1 1 d . . . C9 C 0.53596(4) 1.05183(12) 0.62695(3) 0.01935(13) Uani 1 1 d . . . H9B H 0.5746(6) 1.021(2) 0.6094(5) 0.029(3) Uiso 1 1 d . . . C10 C 0.52923(4) 1.23805(14) 0.65060(4) 0.02487(15) Uani 1 1 d . . . H10A H 0.5644(7) 1.347(2) 0.6510(6) 0.035(3) Uiso 1 1 d . . . H10B H 0.4909(6) 1.269(2) 0.6698(6) 0.034(3) Uiso 1 1 d . . . C11 C 0.26414(3) 0.66613(13) 0.40155(3) 0.01931(13) Uani 1 1 d . . . H11A H 0.2295(6) 0.556(2) 0.3982(5) 0.030(3) Uiso 1 1 d . . . H11B H 0.2442(7) 0.786(2) 0.4192(6) 0.037(3) Uiso 1 1 d . . . C12 C 0.28087(3) 0.72647(14) 0.34289(3) 0.02111(14) Uani 1 1 d . . . H12A H 0.3019(7) 0.605(2) 0.3253(6) 0.038(3) Uiso 1 1 d . . . H12B H 0.3125(6) 0.842(2) 0.3442(6) 0.033(3) Uiso 1 1 d . . . C13 C 0.22013(3) 0.79233(12) 0.31000(3) 0.01746(12) Uani 1 1 d . . . C14 C 0.18409(4) 0.64573(14) 0.27819(3) 0.02287(14) Uani 1 1 d . . . H14 H 0.2005(6) 0.503(2) 0.2749(5) 0.035(3) Uiso 1 1 d . . . C15 C 0.12502(4) 0.70144(17) 0.25157(4) 0.02855(17) Uani 1 1 d . . . H15 H 0.1002(7) 0.598(2) 0.2307(6) 0.041(4) Uiso 1 1 d . . . C16 C 0.10166(4) 0.90448(17) 0.25654(4) 0.02811(18) Uani 1 1 d . . . H16 H 0.0597(6) 0.938(2) 0.2384(6) 0.040(4) Uiso 1 1 d . . . C17 C 0.13764(4) 1.05297(15) 0.28732(4) 0.02564(16) Uani 1 1 d . . . H17 H 0.1210(7) 1.197(2) 0.2896(6) 0.036(3) Uiso 1 1 d . . . C18 C 0.19659(4) 0.99751(13) 0.31394(3) 0.02092(13) Uani 1 1 d . . . H18 H 0.2213(6) 1.100(2) 0.3356(5) 0.027(3) Uiso 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 O1 0.01490(19) 0.0112(2) 0.0210(2) 0.00248(16) 0.00326(16) 0.00326(15) N1 0.0148(2) 0.0121(2) 0.0148(2) -0.00020(17) -0.00087(17) -0.00091(17) C1 0.0120(2) 0.0099(2) 0.0167(3) 0.00062(18) 0.00136(18) 0.00036(17) O2 0.0220(2) 0.0180(2) 0.0258(3) -0.0059(2) -0.0039(2) -0.00209(18) C2 0.0119(2) 0.0138(3) 0.0177(3) -0.0003(2) 0.00084(19) -0.00057(18) C3 0.0128(2) 0.0149(3) 0.0171(3) 0.0016(2) 0.00023(19) 0.00153(19) C4 0.0156(2) 0.0115(3) 0.0181(3) 0.0015(2) 0.0005(2) 0.00124(19) C5 0.0123(2) 0.0105(2) 0.0153(2) 0.00083(19) 0.00016(18) -0.00044(18) C6 0.0174(3) 0.0151(3) 0.0210(3) 0.0007(2) 0.0062(2) -0.0020(2) C7 0.0160(2) 0.0140(3) 0.0154(3) 0.0001(2) 0.00040(19) -0.0025(2) C8 0.0240(3) 0.0187(3) 0.0156(3) -0.0017(2) -0.0008(2) -0.0039(2) C9 0.0186(3) 0.0194(3) 0.0196(3) -0.0042(2) -0.0026(2) -0.0009(2) C10 0.0242(3) 0.0211(3) 0.0288(4) -0.0070(3) -0.0026(3) -0.0002(3) C11 0.0138(3) 0.0250(3) 0.0190(3) 0.0047(2) 0.0001(2) 0.0040(2) C12 0.0138(3) 0.0297(4) 0.0198(3) 0.0049(3) 0.0005(2) 0.0020(2) C13 0.0147(2) 0.0232(3) 0.0145(3) 0.0030(2) 0.0009(2) 0.0006(2) C14 0.0233(3) 0.0254(4) 0.0196(3) -0.0019(3) -0.0006(2) 0.0002(3) C15 0.0242(4) 0.0392(5) 0.0214(3) 0.0004(3) -0.0053(3) -0.0059(3) C16 0.0176(3) 0.0427(5) 0.0234(3) 0.0125(3) -0.0028(3) 0.0008(3) C17 0.0217(3) 0.0271(4) 0.0284(4) 0.0101(3) 0.0033(3) 0.0055(3) C18 0.0199(3) 0.0216(3) 0.0212(3) 0.0030(3) 0.0010(2) -0.0004(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 1.4062(8) . ? O1 H1A 0.894(14) . ? N1 C7 1.4654(9) . ? N1 C8 1.4711(9) . ? N1 H1B 0.908(12) . ? C1 C6 1.5322(9) . ? C1 C2 1.5392(9) . ? C1 C5 1.5479(9) . ? O2 C2 1.2166(9) . ? C2 C3 1.4761(10) . ? C3 C4 1.3458(10) . ? C3 C11 1.4963(10) . ? C4 C5 1.5097(9) . ? C4 H4 0.955(11) . ? C5 C7 1.5261(9) . ? C5 H5 0.997(11) . ? C6 H6A 0.999(12) . ? C6 H6B 1.003(13) . ? C6 H6C 1.003(12) . ? C7 H7A 0.979(11) . ? C7 H7B 0.993(11) . ? C8 C9 1.4963(11) . ? C8 H8A 0.997(12) . ? C8 H8B 0.996(13) . ? C9 C10 1.3221(11) . ? C9 H9B 0.952(12) . ? C10 H10A 1.006(14) . ? C10 H10B 0.967(13) . ? C11 C12 1.5295(11) . ? C11 H11A 1.001(13) . ? C11 H11B 0.975(14) . ? C12 C13 1.5072(10) . ? C12 H12A 0.993(14) . ? C12 H12B 0.982(14) . ? C13 C14 1.3931(11) . ? C13 C18 1.3941(11) . ? C14 C15 1.3945(12) . ? C14 H14 0.971(14) . ? C15 C16 1.3826(15) . ? C15 H15 0.958(15) . ? C16 C17 1.3879(14) . ? C16 H16 0.974(13) . ? C17 C18 1.3921(11) . ? C17 H17 0.976(14) . ? C18 H18 0.959(13) . ? 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 O1 H1A 112.6(9) . . ? C7 N1 C8 112.08(5) . . ? C7 N1 H1B 108.1(7) . . ? C8 N1 H1B 108.6(7) . . ? O1 C1 C6 105.91(5) . . ? O1 C1 C2 114.47(5) . . ? C6 C1 C2 106.02(5) . . ? O1 C1 C5 114.81(5) . . ? C6 C1 C5 113.09(5) . . ? C2 C1 C5 102.41(5) . . ? O2 C2 C3 127.29(6) . . ? O2 C2 C1 125.42(6) . . ? C3 C2 C1 107.26(5) . . ? C4 C3 C2 108.10(6) . . ? C4 C3 C11 128.27(7) . . ? C2 C3 C11 123.61(6) . . ? C3 C4 C5 113.48(6) . . ? C3 C4 H4 124.7(7) . . ? C5 C4 H4 121.8(7) . . ? C4 C5 C7 115.83(6) . . ? C4 C5 C1 102.55(5) . . ? C7 C5 C1 115.09(5) . . ? C4 C5 H5 108.4(6) . . ? C7 C5 H5 107.3(6) . . ? C1 C5 H5 107.2(6) . . ? C1 C6 H6A 112.5(7) . . ? C1 C6 H6B 109.4(7) . . ? H6A C6 H6B 106.5(10) . . ? C1 C6 H6C 109.5(7) . . ? H6A C6 H6C 109.6(10) . . ? H6B C6 H6C 109.2(10) . . ? N1 C7 C5 111.32(5) . . ? N1 C7 H7A 111.8(6) . . ? C5 C7 H7A 111.3(6) . . ? N1 C7 H7B 107.4(6) . . ? C5 C7 H7B 108.9(6) . . ? H7A C7 H7B 105.8(9) . . ? N1 C8 C9 110.43(6) . . ? N1 C8 H8A 110.8(7) . . ? C9 C8 H8A 111.5(7) . . ? N1 C8 H8B 105.8(7) . . ? C9 C8 H8B 110.5(7) . . ? H8A C8 H8B 107.6(10) . . ? C10 C9 C8 124.56(7) . . ? C10 C9 H9B 119.4(8) . . ? C8 C9 H9B 116.0(8) . . ? C9 C10 H10A 121.4(8) . . ? C9 C10 H10B 120.0(8) . . ? H10A C10 H10B 118.5(11) . . ? C3 C11 C12 115.83(6) . . ? C3 C11 H11A 109.5(7) . . ? C12 C11 H11A 107.6(7) . . ? C3 C11 H11B 108.8(8) . . ? C12 C11 H11B 109.8(8) . . ? H11A C11 H11B 104.7(11) . . ? C13 C12 C11 109.02(6) . . ? C13 C12 H12A 111.4(8) . . ? C11 C12 H12A 109.7(8) . . ? C13 C12 H12B 110.4(8) . . ? C11 C12 H12B 110.3(8) . . ? H12A C12 H12B 106.0(11) . . ? C14 C13 C18 118.72(7) . . ? C14 C13 C12 120.62(7) . . ? C18 C13 C12 120.51(7) . . ? C13 C14 C15 120.82(8) . . ? C13 C14 H14 119.1(8) . . ? C15 C14 H14 120.1(8) . . ? C16 C15 C14 119.93(8) . . ? C16 C15 H15 120.3(9) . . ? C14 C15 H15 119.8(9) . . ? C15 C16 C17 119.79(7) . . ? C15 C16 H16 118.3(9) . . ? C17 C16 H16 121.9(9) . . ? C16 C17 C18 120.32(8) . . ? C16 C17 H17 118.8(8) . . ? C18 C17 H17 120.8(8) . . ? C17 C18 C13 120.40(8) . . ? C17 C18 H18 120.4(7) . . ? C13 C18 H18 119.2(7) . . ? 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 O1 C1 C2 O2 33.43(9) . . . . ? C6 C1 C2 O2 -82.93(8) . . . . ? C5 C1 C2 O2 158.33(7) . . . . ? O1 C1 C2 C3 -148.75(5) . . . . ? C6 C1 C2 C3 94.89(6) . . . . ? C5 C1 C2 C3 -23.86(6) . . . . ? O2 C2 C3 C4 -167.25(7) . . . . ? C1 C2 C3 C4 14.99(7) . . . . ? O2 C2 C3 C11 13.93(11) . . . . ? C1 C2 C3 C11 -163.83(6) . . . . ? C2 C3 C4 C5 0.92(8) . . . . ? C11 C3 C4 C5 179.67(6) . . . . ? C3 C4 C5 C7 -142.19(6) . . . . ? C3 C4 C5 C1 -16.01(7) . . . . ? O1 C1 C5 C4 147.74(5) . . . . ? C6 C1 C5 C4 -90.57(6) . . . . ? C2 C1 C5 C4 23.06(6) . . . . ? O1 C1 C5 C7 -85.60(7) . . . . ? C6 C1 C5 C7 36.09(8) . . . . ? C2 C1 C5 C7 149.72(5) . . . . ? C8 N1 C7 C5 179.76(6) . . . . ? C4 C5 C7 N1 -78.78(7) . . . . ? C1 C5 C7 N1 161.67(5) . . . . ? C7 N1 C8 C9 175.31(6) . . . . ? N1 C8 C9 C10 125.11(8) . . . . ? C4 C3 C11 C12 89.97(10) . . . . ? C2 C3 C11 C12 -91.46(9) . . . . ? C3 C11 C12 C13 177.44(7) . . . . ? C11 C12 C13 C14 -92.32(9) . . . . ? C11 C12 C13 C18 83.14(9) . . . . ? C18 C13 C14 C15 -1.16(11) . . . . ? C12 C13 C14 C15 174.37(7) . . . . ? C13 C14 C15 C16 0.10(13) . . . . ? C14 C15 C16 C17 1.02(13) . . . . ? C15 C16 C17 C18 -1.06(13) . . . . ? C16 C17 C18 C13 -0.02(12) . . . . ? C14 C13 C18 C17 1.12(11) . . . . ? C12 C13 C18 C17 -174.42(7) . . . . ? loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA _geom_hbond_site_symmetry_A O1 H1A N1 0.894(14) 1.862(14) 2.7265(8) 162.1(13) 5_666 N1 H1B O1 0.908(12) 2.108(12) 2.9969(8) 166.0(10) 1_565 _diffrn_measured_fraction_theta_max 0.989 _diffrn_reflns_theta_full 37.78 _diffrn_measured_fraction_theta_full 0.989 _refine_diff_density_max 0.560 _refine_diff_density_min -0.283 _refine_diff_density_rms 0.069