data_baran107 _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C19 H23 N O' _chemical_formula_weight 281.38 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 Monoclinic _symmetry_space_group_name_H-M P2(1) loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z' _cell_length_a 11.2351(10) _cell_length_b 5.6546(5) _cell_length_c 11.9800(10) _cell_angle_alpha 90.00 _cell_angle_beta 96.909(5) _cell_angle_gamma 90.00 _cell_volume 755.56(11) _cell_formula_units_Z 2 _cell_measurement_temperature 296(2) _cell_measurement_reflns_used 3326 _cell_measurement_theta_min 3.72 _cell_measurement_theta_max 63.98 _exptl_crystal_description blade _exptl_crystal_colour colorless _exptl_crystal_size_max 0.31 _exptl_crystal_size_mid 0.10 _exptl_crystal_size_min 0.04 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.237 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 304 _exptl_absorpt_coefficient_mu 0.582 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.8401 _exptl_absorpt_correction_T_max 0.9771 _exptl_absorpt_process_details sadabs _exptl_special_details ; ? ; _diffrn_ambient_temperature 296(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 'Bruker APEX-II CCD' _diffrn_measurement_method '\f and \w scans' _diffrn_reflns_number 5050 _diffrn_reflns_av_R_equivalents 0.0390 _diffrn_reflns_av_sigmaI/netI 0.0481 _diffrn_reflns_limit_h_min -11 _diffrn_reflns_limit_h_max 12 _diffrn_reflns_limit_k_min -6 _diffrn_reflns_limit_k_max 6 _diffrn_reflns_limit_l_min -13 _diffrn_reflns_limit_l_max 13 _diffrn_reflns_theta_min 5.10 _diffrn_reflns_theta_max 64.92 _reflns_number_total 2231 _reflns_number_gt 1983 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker APEX2' _computing_cell_refinement 'Bruker SAINT' _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^)+(0.0500P)^2^+0.0300P] 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 SHELXL _refine_ls_extinction_coef 0.0093(12) _refine_ls_extinction_expression 'Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^' _refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _refine_ls_abs_structure_Flack 0.2(4) _refine_ls_number_reflns 2231 _refine_ls_number_parameters 191 _refine_ls_number_restraints 1 _refine_ls_R_factor_all 0.0481 _refine_ls_R_factor_gt 0.0398 _refine_ls_wR_factor_ref 0.0966 _refine_ls_wR_factor_gt 0.0927 _refine_ls_goodness_of_fit_ref 1.087 _refine_ls_restrained_S_all 1.087 _refine_ls_shift/su_max 0.005 _refine_ls_shift/su_mean 0.001 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 0.05845(14) 0.6832(3) 0.84206(14) 0.0317(5) Uani 1 1 d . . . N1 N 0.06592(17) 0.1448(4) 0.61229(15) 0.0279(5) Uani 1 1 d . . . H1A H 0.0128 0.0349 0.6025 0.034 Uiso 1 1 calc R . . C1 C 0.2224(2) 0.7632(4) 0.98382(18) 0.0245(5) Uani 1 1 d . . . C2 C 0.1652(2) 0.6652(4) 0.87139(19) 0.0235(5) Uani 1 1 d . . . C3 C 0.25116(19) 0.5625(4) 0.79329(18) 0.0204(5) Uani 1 1 d . . . H3A H 0.3044 0.4527 0.8387 0.025 Uiso 1 1 calc R . . C4 C 0.3298(2) 0.7733(4) 0.76351(18) 0.0220(5) Uani 1 1 d . . . H4A H 0.2758 0.8953 0.7283 0.026 Uiso 1 1 calc R . . C5 C 0.3945(2) 0.8778(4) 0.87138(19) 0.0275(6) Uani 1 1 d . . . H5A H 0.4497 0.7608 0.9071 0.033 Uiso 1 1 calc R . . H5B H 0.4413 1.0129 0.8524 0.033 Uiso 1 1 calc R . . C6 C 0.3103(2) 0.9554(4) 0.95454(19) 0.0274(6) Uani 1 1 d . . . H6A H 0.2646 1.0907 0.9236 0.033 Uiso 1 1 calc R . . H6B H 0.3578 1.0065 1.0233 0.033 Uiso 1 1 calc R . . C7 C 0.18829(19) 0.4222(4) 0.69824(18) 0.0204(5) Uani 1 1 d . . . C8 C 0.20691(19) 0.4131(4) 0.58154(18) 0.0210(5) Uani 1 1 d . . . C9 C 0.28181(19) 0.5336(4) 0.51362(19) 0.0245(6) Uani 1 1 d . . . C10 C 0.3669(2) 0.7273(5) 0.55735(18) 0.0271(6) Uani 1 1 d . . . H10A H 0.3248 0.8768 0.5462 0.032 Uiso 1 1 calc R . . H10B H 0.4322 0.7304 0.5113 0.032 Uiso 1 1 calc R . . C11 C 0.42125(19) 0.7141(4) 0.68027(19) 0.0257(6) Uani 1 1 d . . . H11A H 0.4816 0.8399 0.6899 0.031 Uiso 1 1 calc R . . C12 C 0.10236(19) 0.2563(4) 0.71227(19) 0.0256(5) Uani 1 1 d . . . H12A H 0.0729 0.2240 0.7800 0.031 Uiso 1 1 calc R . . C13 C 0.12770(19) 0.2367(4) 0.53050(19) 0.0244(5) Uani 1 1 d . . . C14 C 0.1189(2) 0.1806(4) 0.4167(2) 0.0300(6) Uani 1 1 d . . . H14A H 0.0653 0.0665 0.3853 0.036 Uiso 1 1 calc R . . C15 C 0.1922(2) 0.3001(5) 0.3529(2) 0.0331(6) Uani 1 1 d . . . H15A H 0.1888 0.2668 0.2765 0.040 Uiso 1 1 calc R . . C16 C 0.2725(2) 0.4722(5) 0.4009(2) 0.0312(6) Uani 1 1 d . . . H16A H 0.3216 0.5485 0.3551 0.037 Uiso 1 1 calc R . . C17 C 0.4896(2) 0.4846(5) 0.7074(2) 0.0318(6) Uani 1 1 d . . . H17A H 0.5444 0.4587 0.6530 0.048 Uiso 1 1 calc R . . H17B H 0.4340 0.3553 0.7051 0.048 Uiso 1 1 calc R . . H17C H 0.5334 0.4951 0.7811 0.048 Uiso 1 1 calc R . . C18 C 0.2872(2) 0.5689(4) 1.05553(19) 0.0319(6) Uani 1 1 d . . . H18A H 0.2304 0.4515 1.0726 0.048 Uiso 1 1 calc R . . H18B H 0.3258 0.6360 1.1241 0.048 Uiso 1 1 calc R . . H18C H 0.3463 0.4968 1.0149 0.048 Uiso 1 1 calc R . . C19 C 0.1283(2) 0.8721(5) 1.0491(2) 0.0399(7) Uani 1 1 d . . . H19A H 0.0736 0.7515 1.0674 0.060 Uiso 1 1 calc R . . H19B H 0.0850 0.9917 1.0042 0.060 Uiso 1 1 calc R . . H19C H 0.1668 0.9417 1.1172 0.060 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 0.0201(10) 0.0442(11) 0.0305(10) -0.0034(8) 0.0012(7) -0.0021(8) N1 0.0267(12) 0.0267(11) 0.0289(12) -0.0037(9) -0.0030(9) -0.0075(9) C1 0.0232(13) 0.0273(12) 0.0227(12) -0.0035(10) 0.0015(9) -0.0004(11) C2 0.0262(15) 0.0224(12) 0.0222(12) 0.0030(9) 0.0042(10) -0.0028(11) C3 0.0186(13) 0.0219(11) 0.0201(12) -0.0009(10) -0.0010(9) 0.0003(11) C4 0.0207(13) 0.0218(12) 0.0232(12) 0.0025(10) 0.0011(9) -0.0037(11) C5 0.0258(14) 0.0271(12) 0.0288(14) -0.0010(11) -0.0007(10) -0.0044(11) C6 0.0309(15) 0.0240(12) 0.0252(14) -0.0014(10) -0.0054(10) 0.0001(12) C7 0.0177(12) 0.0183(11) 0.0239(13) -0.0008(9) -0.0024(9) 0.0004(10) C8 0.0185(13) 0.0229(12) 0.0204(12) -0.0007(9) -0.0027(9) 0.0031(11) C9 0.0226(13) 0.0265(12) 0.0241(13) -0.0003(10) 0.0015(10) 0.0039(11) C10 0.0259(13) 0.0312(14) 0.0245(13) 0.0028(11) 0.0046(10) -0.0028(12) C11 0.0210(13) 0.0299(14) 0.0263(13) 0.0019(11) 0.0030(9) -0.0027(12) C12 0.0270(13) 0.0252(12) 0.0239(12) -0.0009(10) -0.0004(10) 0.0004(12) C13 0.0215(13) 0.0254(12) 0.0253(12) -0.0019(10) -0.0011(9) 0.0028(11) C14 0.0286(15) 0.0283(13) 0.0313(14) -0.0064(11) -0.0037(11) 0.0024(12) C15 0.0341(15) 0.0417(16) 0.0224(13) -0.0055(12) -0.0014(11) 0.0077(13) C16 0.0283(14) 0.0409(15) 0.0248(14) 0.0018(11) 0.0044(10) 0.0046(13) C17 0.0273(14) 0.0406(15) 0.0275(14) 0.0005(12) 0.0037(10) 0.0065(13) C18 0.0464(16) 0.0273(13) 0.0207(13) -0.0005(11) -0.0016(11) 0.0014(13) C19 0.0378(16) 0.0500(18) 0.0320(15) -0.0141(14) 0.0041(11) -0.0013(14) _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 C2 1.212(3) . ? N1 C13 1.369(3) . ? N1 C12 1.372(3) . ? C1 C19 1.519(3) . ? C1 C18 1.525(3) . ? C1 C2 1.525(3) . ? C1 C6 1.537(3) . ? C2 C3 1.538(3) . ? C3 C7 1.494(3) . ? C3 C4 1.551(3) . ? C4 C5 1.523(3) . ? C4 C11 1.552(3) . ? C5 C6 1.519(3) . ? C7 C12 1.371(3) . ? C7 C8 1.439(3) . ? C8 C9 1.414(3) . ? C8 C13 1.425(3) . ? C9 C16 1.386(3) . ? C9 C10 1.506(3) . ? C10 C11 1.527(3) . ? C11 C17 1.523(3) . ? C13 C14 1.392(3) . ? C14 C15 1.368(3) . ? C15 C16 1.402(3) . ? 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 C13 N1 C12 109.1(2) . . ? C19 C1 C18 108.47(19) . . ? C19 C1 C2 110.89(18) . . ? C18 C1 C2 111.0(2) . . ? C19 C1 C6 109.7(2) . . ? C18 C1 C6 111.19(18) . . ? C2 C1 C6 105.63(17) . . ? O1 C2 C1 121.5(2) . . ? O1 C2 C3 121.8(2) . . ? C1 C2 C3 116.46(19) . . ? C7 C3 C2 112.97(18) . . ? C7 C3 C4 117.58(18) . . ? C2 C3 C4 105.48(18) . . ? C5 C4 C11 110.11(17) . . ? C5 C4 C3 109.25(18) . . ? C11 C4 C3 114.93(18) . . ? C6 C5 C4 113.40(18) . . ? C5 C6 C1 114.40(19) . . ? C12 C7 C8 106.34(19) . . ? C12 C7 C3 123.0(2) . . ? C8 C7 C3 130.5(2) . . ? C9 C8 C13 118.3(2) . . ? C9 C8 C7 135.1(2) . . ? C13 C8 C7 106.61(19) . . ? C16 C9 C8 117.3(2) . . ? C16 C9 C10 119.5(2) . . ? C8 C9 C10 123.2(2) . . ? C9 C10 C11 117.63(19) . . ? C17 C11 C10 112.4(2) . . ? C17 C11 C4 113.7(2) . . ? C10 C11 C4 112.98(18) . . ? C7 C12 N1 110.4(2) . . ? N1 C13 C14 129.2(2) . . ? N1 C13 C8 107.62(19) . . ? C14 C13 C8 123.2(2) . . ? C15 C14 C13 117.2(2) . . ? C14 C15 C16 121.0(2) . . ? C9 C16 C15 122.9(2) . . ? _diffrn_measured_fraction_theta_max 0.962 _diffrn_reflns_theta_full 55.00 _diffrn_measured_fraction_theta_full 0.995 _refine_diff_density_max 0.186 _refine_diff_density_min -0.168 _refine_diff_density_rms 0.039