data_03hur981 _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C18 H19 N O2' _chemical_formula_weight 281.34 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 triclinic _symmetry_space_group_name_H-M P-1 _symmetry_space_group_name_hall '-P 1' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 7.9300(10) _cell_length_b 8.7170(6) _cell_length_c 11.6550(10) _cell_angle_alpha 75.190(8) _cell_angle_beta 78.740(9) _cell_angle_gamma 89.930(7) _cell_volume 762.90(13) _cell_formula_units_Z 2 _cell_measurement_temperature 150(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description ? _exptl_crystal_colour ? _exptl_crystal_size_max 0.25 _exptl_crystal_size_mid 0.18 _exptl_crystal_size_min 0.12 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.225 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 300 _exptl_absorpt_coefficient_mu 0.080 _exptl_absorpt_correction_type none _diffrn_ambient_temperature 150(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'rotating anode generator' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Delft instruments FAST area detector' _diffrn_measurement_method 'Intensity measurements as described by Darr, Drake, Hursthouse & Malik (1993)' _diffrn_standards_number 'None' _diffrn_standards_interval_count 'N/A' _diffrn_standards_interval_time 'N/A' _diffrn_standards_decay_% 'N/A' _diffrn_reflns_number 2040 _diffrn_reflns_av_R_equivalents 0.0000 _diffrn_reflns_av_sigmaI/netI 0.0905 _diffrn_reflns_limit_h_min -8 _diffrn_reflns_limit_h_max 8 _diffrn_reflns_limit_k_min -9 _diffrn_reflns_limit_k_max 9 _diffrn_reflns_limit_l_min 0 _diffrn_reflns_limit_l_max 13 _diffrn_reflns_theta_min 3.41 _diffrn_reflns_theta_max 24.92 _reflns_number_total 2040 _reflns_number_gt 1377 _reflns_threshold_expression >2\s(I) _computing_data_collection 'MADNES (Pflugrath & Messerschmidt, 1989)' _computing_cell_refinement REFINE _computing_data_reduction 'ABSURD (Karaulov, 1992)' _computing_structure_solution 'SIR92 (Altomare, Cascarano, Giacovazzo & Guaglitardi, 1993)' _computing_structure_refinement 'SHELXL97 (Sheldrick, 2008)' _computing_publication_material SHELXL97 _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^ > 2\s(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^)+(0.0410P)^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 0 _refine_ls_number_reflns 2040 _refine_ls_number_parameters 192 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0617 _refine_ls_R_factor_gt 0.0422 _refine_ls_wR_factor_ref 0.1014 _refine_ls_wR_factor_gt 0.0953 _refine_ls_goodness_of_fit_ref 0.909 _refine_ls_restrained_S_all 0.909 _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 1.0841(2) 0.24459(17) 0.78481(16) 0.0309(5) Uani 1 1 d . . . O2 O 0.8321(2) -0.1170(2) 0.64163(17) 0.0383(5) Uani 1 1 d . . . N1 N 0.9663(2) 0.0569(2) 0.71532(18) 0.0221(5) Uani 1 1 d . . . C15 C 1.1184(3) -0.0391(3) 0.7288(2) 0.0254(6) Uani 1 1 d . . . H15B H 1.2231 0.0328 0.6990 0.030 Uiso 1 1 calc R . . H15A H 1.1246 -0.1133 0.6766 0.030 Uiso 1 1 calc R . . C2 C 0.7821(3) 0.2506(2) 0.7985(2) 0.0199(6) Uani 1 1 d . . . C16 C 1.1196(3) -0.1345(3) 0.8574(2) 0.0240(6) Uani 1 1 d . . . H16 H 1.1103 -0.0593 0.9100 0.029 Uiso 1 1 calc R . . C9 C 0.7692(3) 0.1523(3) 0.5733(2) 0.0220(6) Uani 1 1 d . . . C1 C 0.9550(3) 0.1897(3) 0.7634(2) 0.0229(6) Uani 1 1 d . . . C3 C 0.6335(3) 0.1510(3) 0.8443(2) 0.0240(6) Uani 1 1 d . . . H3 H 0.6394 0.0406 0.8497 0.029 Uiso 1 1 calc R . . C14 C 0.8610(3) 0.2948(3) 0.5094(2) 0.0274(6) Uani 1 1 d . . . H14 H 0.9762 0.3120 0.5169 0.033 Uiso 1 1 calc R . . C10 C 0.6021(3) 0.1289(3) 0.5598(2) 0.0269(6) Uani 1 1 d . . . H10 H 0.5398 0.0310 0.6010 0.032 Uiso 1 1 calc R . . C13 C 0.7835(4) 0.4109(3) 0.4351(2) 0.0334(7) Uani 1 1 d . . . H13 H 0.8462 0.5076 0.3910 0.040 Uiso 1 1 calc R . . C6 C 0.6146(3) 0.4734(3) 0.8286(2) 0.0287(7) Uani 1 1 d . . . H6 H 0.6078 0.5838 0.8231 0.034 Uiso 1 1 calc R . . C17 C 1.2909(3) -0.2124(3) 0.8588(2) 0.0342(7) Uani 1 1 d . . . H17A H 1.2942 -0.2731 0.9415 0.051 Uiso 1 1 calc R . . H17C H 1.3848 -0.1303 0.8302 0.051 Uiso 1 1 calc R . . H17B H 1.3041 -0.2840 0.8054 0.051 Uiso 1 1 calc R . . C7 C 0.7714(3) 0.4128(3) 0.7921(2) 0.0261(6) Uani 1 1 d . . . H7 H 0.8721 0.4814 0.7626 0.031 Uiso 1 1 calc R . . C4 C 0.4776(3) 0.2124(3) 0.8818(2) 0.0280(7) Uani 1 1 d . . . H4 H 0.3770 0.1439 0.9136 0.034 Uiso 1 1 calc R . . C5 C 0.4676(3) 0.3741(3) 0.8731(2) 0.0313(7) Uani 1 1 d . . . H5 H 0.3600 0.4162 0.8977 0.038 Uiso 1 1 calc R . . C12 C 0.6169(4) 0.3876(3) 0.4245(2) 0.0328(7) Uani 1 1 d . . . H12 H 0.5641 0.4687 0.3742 0.039 Uiso 1 1 calc R . . C8 C 0.8522(3) 0.0195(3) 0.6476(2) 0.0250(6) Uani 1 1 d . . . C11 C 0.5260(4) 0.2469(3) 0.4868(2) 0.0339(7) Uani 1 1 d . . . H11 H 0.4105 0.2311 0.4795 0.041 Uiso 1 1 calc R . . C18 C 0.9692(4) -0.2566(3) 0.9072(3) 0.0422(8) Uani 1 1 d . . . H18A H 0.8612 -0.2037 0.9000 0.063 Uiso 1 1 calc R . . H18C H 0.9679 -0.3078 0.9927 0.063 Uiso 1 1 calc R . . H18B H 0.9814 -0.3369 0.8611 0.063 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 0.0231(11) 0.0308(9) 0.0434(13) -0.0140(9) -0.0117(9) -0.0009(8) O2 0.0434(13) 0.0264(10) 0.0552(15) -0.0188(9) -0.0233(10) 0.0085(8) N1 0.0182(12) 0.0261(11) 0.0271(14) -0.0121(10) -0.0095(10) 0.0067(9) C15 0.0232(15) 0.0273(13) 0.0282(17) -0.0100(12) -0.0077(12) 0.0108(11) C2 0.0218(15) 0.0221(12) 0.0178(16) -0.0066(11) -0.0067(12) 0.0039(11) C16 0.0286(16) 0.0217(12) 0.0264(17) -0.0120(11) -0.0094(13) 0.0050(11) C9 0.0229(15) 0.0249(13) 0.0219(16) -0.0133(11) -0.0039(12) 0.0025(11) C1 0.0288(17) 0.0209(13) 0.0175(16) -0.0029(11) -0.0037(13) 0.0014(11) C3 0.0273(16) 0.0209(12) 0.0256(17) -0.0097(11) -0.0046(12) 0.0019(11) C14 0.0303(16) 0.0331(14) 0.0215(17) -0.0121(12) -0.0049(13) 0.0021(12) C10 0.0282(16) 0.0294(13) 0.0278(17) -0.0122(12) -0.0102(13) 0.0049(11) C13 0.049(2) 0.0274(13) 0.0237(17) -0.0087(12) -0.0036(14) 0.0025(13) C6 0.0321(17) 0.0224(12) 0.0333(18) -0.0104(12) -0.0068(13) 0.0049(12) C17 0.0388(18) 0.0385(14) 0.0300(18) -0.0096(13) -0.0172(14) 0.0182(13) C7 0.0266(16) 0.0257(13) 0.0264(17) -0.0087(12) -0.0042(12) -0.0003(11) C4 0.0247(16) 0.0318(14) 0.0244(17) -0.0044(12) -0.0016(12) 0.0026(11) C5 0.0299(17) 0.0381(15) 0.0251(17) -0.0081(12) -0.0036(13) 0.0151(13) C12 0.047(2) 0.0339(15) 0.0216(18) -0.0084(12) -0.0147(14) 0.0159(14) C8 0.0199(15) 0.0263(14) 0.0304(18) -0.0125(12) -0.0021(13) 0.0047(11) C11 0.0315(17) 0.0439(16) 0.0347(19) -0.0183(14) -0.0159(14) 0.0099(13) C18 0.0406(19) 0.0438(15) 0.037(2) 0.0006(14) -0.0093(15) -0.0030(14) _geom_special_details ; All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell s.u.'s are taken into account individually in the estimation of s.u.'s in distances, angles and torsion angles; correlations between s.u.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell s.u.'s is used for estimating s.u.'s 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 1.225(3) . ? O2 C8 1.222(2) . ? N1 C8 1.399(3) . ? N1 C1 1.405(3) . ? N1 C15 1.478(3) . ? C15 C16 1.518(3) . ? C15 H15B 0.9900 . ? C15 H15A 0.9900 . ? C2 C3 1.395(3) . ? C2 C7 1.400(3) . ? C2 C1 1.490(3) . ? C16 C17 1.519(3) . ? C16 C18 1.520(3) . ? C16 H16 1.0000 . ? C9 C10 1.386(3) . ? C9 C14 1.395(3) . ? C9 C8 1.494(3) . ? C3 C4 1.383(3) . ? C3 H3 0.9500 . ? C14 C13 1.382(3) . ? C14 H14 0.9500 . ? C10 C11 1.377(3) . ? C10 H10 0.9500 . ? C13 C12 1.370(4) . ? C13 H13 0.9500 . ? C6 C7 1.384(3) . ? C6 C5 1.384(3) . ? C6 H6 0.9500 . ? C17 H17A 0.9800 . ? C17 H17C 0.9800 . ? C17 H17B 0.9800 . ? C7 H7 0.9500 . ? C4 C5 1.390(3) . ? C4 H4 0.9500 . ? C5 H5 0.9500 . ? C12 C11 1.376(3) . ? C12 H12 0.9500 . ? C11 H11 0.9500 . ? C18 H18A 0.9800 . ? C18 H18C 0.9800 . ? C18 H18B 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 C8 N1 C1 124.2(2) . . ? C8 N1 C15 118.91(19) . . ? C1 N1 C15 116.6(2) . . ? N1 C15 C16 114.77(19) . . ? N1 C15 H15B 108.6 . . ? C16 C15 H15B 108.6 . . ? N1 C15 H15A 108.6 . . ? C16 C15 H15A 108.6 . . ? H15B C15 H15A 107.6 . . ? C3 C2 C7 119.1(2) . . ? C3 C2 C1 122.56(19) . . ? C7 C2 C1 118.2(2) . . ? C15 C16 C17 108.6(2) . . ? C15 C16 C18 112.1(2) . . ? C17 C16 C18 111.5(2) . . ? C15 C16 H16 108.2 . . ? C17 C16 H16 108.2 . . ? C18 C16 H16 108.2 . . ? C10 C9 C14 119.2(2) . . ? C10 C9 C8 119.3(2) . . ? C14 C9 C8 121.3(2) . . ? O1 C1 N1 119.8(2) . . ? O1 C1 C2 121.3(2) . . ? N1 C1 C2 118.7(2) . . ? C4 C3 C2 120.3(2) . . ? C4 C3 H3 119.9 . . ? C2 C3 H3 119.9 . . ? C13 C14 C9 119.6(2) . . ? C13 C14 H14 120.2 . . ? C9 C14 H14 120.2 . . ? C11 C10 C9 120.3(2) . . ? C11 C10 H10 119.8 . . ? C9 C10 H10 119.8 . . ? C12 C13 C14 120.6(2) . . ? C12 C13 H13 119.7 . . ? C14 C13 H13 119.7 . . ? C7 C6 C5 120.3(2) . . ? C7 C6 H6 119.8 . . ? C5 C6 H6 119.8 . . ? C16 C17 H17A 109.5 . . ? C16 C17 H17C 109.5 . . ? H17A C17 H17C 109.5 . . ? C16 C17 H17B 109.5 . . ? H17A C17 H17B 109.5 . . ? H17C C17 H17B 109.5 . . ? C6 C7 C2 120.2(2) . . ? C6 C7 H7 119.9 . . ? C2 C7 H7 119.9 . . ? C3 C4 C5 120.2(2) . . ? C3 C4 H4 119.9 . . ? C5 C4 H4 119.9 . . ? C6 C5 C4 119.9(2) . . ? C6 C5 H5 120.1 . . ? C4 C5 H5 120.1 . . ? C13 C12 C11 120.1(2) . . ? C13 C12 H12 120.0 . . ? C11 C12 H12 120.0 . . ? O2 C8 N1 120.6(2) . . ? O2 C8 C9 120.7(2) . . ? N1 C8 C9 118.4(2) . . ? C12 C11 C10 120.2(3) . . ? C12 C11 H11 119.9 . . ? C10 C11 H11 119.9 . . ? C16 C18 H18A 109.5 . . ? C16 C18 H18C 109.5 . . ? H18A C18 H18C 109.5 . . ? C16 C18 H18B 109.5 . . ? H18A C18 H18B 109.5 . . ? H18C C18 H18B 109.5 . . ? _diffrn_measured_fraction_theta_max 0.768 _diffrn_reflns_theta_full 24.92 _diffrn_measured_fraction_theta_full 0.768 _refine_diff_density_max 0.168 _refine_diff_density_min -0.193 _refine_diff_density_rms 0.046