# Copyright The Royal Society of Chemistry, 1999 # CCDC Number: 182/1130 data_esr3 _audit_creation_method SHELXL _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_formula_moiety ? _chemical_formula_structural ? _chemical_formula_analytical ? _chemical_formula_sum 'C17 H23 N O4' _chemical_formula_weight 305.36 _chemical_melting_point ? _chemical_compound_source ? loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source 'C' 'C' .0181 .0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 'H' 'H' .0000 .0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 'N' 'N' .0311 .0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 'O' 'O' .0492 .0322 '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 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 7.7540(11) _cell_length_b 8.8328(12) _cell_length_c 12.476(2) _cell_angle_alpha 78.530(14) _cell_angle_beta 89.250(12) _cell_angle_gamma 81.025(9) _cell_volume 827.0(2) _cell_formula_units_Z 2 _cell_measurement_temperature 160(2) _cell_measurement_reflns_used 36 _cell_measurement_theta_min 25.23 _cell_measurement_theta_max 27.36 _exptl_crystal_description prism _exptl_crystal_colour colourless _exptl_crystal_size_max 0.44 _exptl_crystal_size_mid 0.17 _exptl_crystal_size_min 0.17 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.226 _exptl_crystal_density_method ? _exptl_crystal_F_000 328 _exptl_absorpt_coefficient_mu 0.709 _exptl_absorpt_correction_type none _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 160(2) _diffrn_radiation_wavelength 1.54184 _diffrn_radiation_type CuK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device 'Stoe-Siemens diffractometer' _diffrn_measurement_method '\w/\q scans with on-line profile fitting' _diffrn_standards_number 5 _diffrn_standards_interval_count ? _diffrn_standards_interval_time 60 _diffrn_standards_decay_% 0 _diffrn_reflns_number 5549 _diffrn_reflns_av_R_equivalents 0.0402 _diffrn_reflns_av_sigmaI/netI 0.0417 _diffrn_reflns_limit_h_min -9 _diffrn_reflns_limit_h_max 9 _diffrn_reflns_limit_k_min -10 _diffrn_reflns_limit_k_max 10 _diffrn_reflns_limit_l_min -14 _diffrn_reflns_limit_l_max 14 _diffrn_reflns_theta_min 3.62 _diffrn_reflns_theta_max 64.96 _reflns_number_total 2778 _reflns_number_observed 2632 _reflns_observed_criterion >2sigma(I) _computing_data_collection 'Stoe DIF4' _computing_cell_refinement 'Stoe DIF4' _computing_data_reduction 'local programs' _computing_structure_solution SHELXTL/PC _computing_structure_refinement SHELXL-93 _computing_molecular_graphics SHELXTL/PC _computing_publication_material 'SHELXL-93 and local programs' _refine_special_details ; Refinement on F^2^ for ALL reflections except for 1 with very gative F^2^ or flagged by the user for potential systematic errors. Weighted R- ctors wR and all goodnesses of fit S are based on F^2^, conventional R- ctors R are based on F, with F set to zero for negative F^2^. The observed iterion of F^2^ > 2sigma(F^2^) is used only for calculating _R_factor_obs c. and is not relevant to the choice of reflections for refinement. R-factors sed on F^2^ are statistically about twice as large as those based on F, d 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 w=1/[\s^2^(Fo^2^)+(0.0531P)^2^+0.2831P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary ? _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment ? _refine_ls_extinction_method SHELXL _refine_ls_extinction_coef 0.0071(8) _refine_ls_extinction_expression 'Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^' _refine_ls_number_reflns 2777 _refine_ls_number_parameters 205 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0488 _refine_ls_R_factor_obs 0.0471 _refine_ls_wR_factor_all 0.1095 _refine_ls_wR_factor_obs 0.1072 _refine_ls_goodness_of_fit_all 1.042 _refine_ls_goodness_of_fit_obs 1.054 _refine_ls_restrained_S_all 1.045 _refine_ls_restrained_S_obs 1.054 _refine_ls_shift/esd_max 0.000 _refine_ls_shift/esd_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_thermal_displace_type _atom_site_occupancy _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_group N1 N -0.08982(15) 1.10679(13) 0.60224(9) 0.0236(3) Uani 1 d . . O1 O 0.09803(12) 0.72271(11) 0.72917(7) 0.0251(2) Uani 1 d . . O2 O 0.16031(13) 0.51223(12) 0.85729(9) 0.0336(3) Uani 1 d . . O3 O -0.43924(14) 0.79815(13) 0.58343(9) 0.0368(3) Uani 1 d . . O4 O 0.04526(15) 1.32118(13) 0.56365(11) 0.0452(3) Uani 1 d . . C1 C 0.0483(2) 0.9991(2) 0.65947(10) 0.0235(3) Uani 1 d . . C2 C 0.2230(2) 1.0343(2) 0.68682(11) 0.0255(3) Uani 1 d . . H2A H 0.2683(2) 1.0964(2) 0.62052(11) 0.031 Uiso 1 calc R . H2B H 0.3042(2) 0.9344(2) 0.70662(11) 0.031 Uiso 1 calc R . C3 C 0.2244(2) 1.1241(2) 0.78070(12) 0.0326(4) Uani 1 d . . H3 H 0.1378(2) 1.2223(2) 0.76203(12) 0.039 Uiso 1 calc R . C4 C 0.1713(3) 1.0285(2) 0.88778(14) 0.0514(5) Uani 1 d . . H4A H 0.0537(8) 1.0042(15) 0.8795(4) 0.077 Uiso 1 calc R . H4B H 0.1719(19) 1.0888(7) 0.9458(3) 0.077 Uiso 1 calc R . H4C H 0.2540(11) 0.9310(8) 0.9071(6) 0.077 Uiso 1 calc R . C5 C 0.4040(2) 1.1691(2) 0.7914(2) 0.0537(5) Uani 1 d . . H5A H 0.4318(8) 1.2362(14) 0.7230(4) 0.081 Uiso 1 calc R . H5B H 0.4916(4) 1.0744(3) 0.8067(12) 0.081 Uiso 1 calc R . H5C H 0.4043(6) 1.2256(15) 0.8515(8) 0.081 Uiso 1 calc R . C6 C -0.0108(2) 0.85946(15) 0.68183(10) 0.0223(3) Uani 1 d . . C7 C 0.0555(2) 0.6257(2) 0.82267(11) 0.0240(3) Uani 1 d . . C8 C -0.1204(2) 0.6651(2) 0.87033(10) 0.0240(3) Uani 1 d . . H8A H -0.1594(2) 0.7794(2) 0.85068(10) 0.029 Uiso 1 calc R . H8B H -0.1113(2) 0.6349(2) 0.95107(10) 0.029 Uiso 1 calc R . C9 C -0.2578(2) 0.5794(2) 0.82803(11) 0.0253(3) Uani 1 d . . C10 C -0.2545(2) 0.5962(2) 0.70206(11) 0.0261(3) Uani 1 d . . H10A H -0.1356(2) 0.5537(2) 0.68144(11) 0.031 Uiso 1 calc R . H10B H -0.3357(2) 0.5307(2) 0.68086(11) 0.031 Uiso 1 calc R . C11 C -0.3026(2) 0.7602(2) 0.63671(11) 0.0249(3) Uani 1 d . . C12 C -0.1848(2) 0.8755(2) 0.63788(10) 0.0227(3) Uani 1 d . . C13 C -0.2279(2) 1.0300(2) 0.59014(11) 0.0239(3) Uani 1 d . . H13 H -0.3360(2) 1.0771(2) 0.55429(11) 0.029 Uiso 1 calc R . C14 C -0.0865(2) 1.2671(2) 0.55644(11) 0.0279(3) Uani 1 d . . C15 C -0.2501(2) 1.3590(2) 0.50120(12) 0.0297(3) Uani 1 d . . H15A H -0.3467(3) 1.3526(11) 0.5525(3) 0.044 Uiso 1 calc R . H15B H -0.2765(8) 1.3162(8) 0.4377(5) 0.044 Uiso 1 calc R . H15C H -0.2347(5) 1.4685(3) 0.4771(8) 0.044 Uiso 1 calc R . C16 C -0.2204(2) 0.4045(2) 0.87824(13) 0.0343(4) Uani 1 d . . H16A H -0.1028(6) 0.3611(3) 0.8586(8) 0.052 Uiso 1 calc R . H16B H -0.3063(9) 0.3509(3) 0.8502(7) 0.052 Uiso 1 calc R . H16C H -0.2282(15) 0.3895(2) 0.95801(14) 0.052 Uiso 1 calc R . C17 C -0.4376(2) 0.6493(2) 0.86340(13) 0.0354(4) Uani 1 d . . H17A H -0.4625(7) 0.7607(4) 0.8298(8) 0.053 Uiso 1 calc R . H17B H -0.4386(5) 0.6369(12) 0.94321(15) 0.053 Uiso 1 calc R . H17C H -0.5268(3) 0.5949(9) 0.8399(8) 0.053 Uiso 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 N1 0.0261(6) 0.0227(6) 0.0229(6) -0.0033(4) 0.0003(5) -0.0082(5) O1 0.0242(5) 0.0237(5) 0.0262(5) -0.0014(4) 0.0032(4) -0.0051(4) O2 0.0277(6) 0.0296(5) 0.0391(6) 0.0032(4) -0.0014(4) -0.0035(4) O3 0.0334(6) 0.0377(6) 0.0388(6) 0.0011(5) -0.0119(5) -0.0148(5) O4 0.0359(6) 0.0293(6) 0.0680(8) 0.0050(5) -0.0111(6) -0.0158(5) C1 0.0255(7) 0.0246(7) 0.0213(6) -0.0052(5) 0.0034(5) -0.0062(5) C2 0.0226(7) 0.0264(7) 0.0285(7) -0.0055(5) 0.0026(5) -0.0075(6) C3 0.0297(8) 0.0351(8) 0.0376(8) -0.0155(7) 0.0003(6) -0.0083(6) C4 0.0624(12) 0.0670(12) 0.0326(9) -0.0196(8) 0.0070(8) -0.0226(10) C5 0.0393(10) 0.0635(12) 0.0723(13) -0.0367(11) -0.0010(9) -0.0209(9) C6 0.0248(7) 0.0222(6) 0.0201(6) -0.0037(5) 0.0030(5) -0.0048(5) C7 0.0257(7) 0.0232(7) 0.0240(7) -0.0027(5) -0.0024(5) -0.0090(6) C8 0.0255(7) 0.0254(7) 0.0214(6) -0.0031(5) 0.0005(5) -0.0068(6) C9 0.0236(7) 0.0264(7) 0.0263(7) -0.0018(5) 0.0002(6) -0.0091(6) C10 0.0293(7) 0.0246(7) 0.0278(7) -0.0072(6) -0.0004(6) -0.0121(6) C11 0.0263(7) 0.0291(7) 0.0216(7) -0.0064(5) 0.0003(6) -0.0098(6) C12 0.0250(7) 0.0248(7) 0.0203(6) -0.0050(5) 0.0018(5) -0.0091(6) C13 0.0239(7) 0.0276(7) 0.0216(6) -0.0052(5) -0.0002(5) -0.0084(6) C14 0.0324(8) 0.0243(7) 0.0285(7) -0.0050(6) 0.0016(6) -0.0092(6) C15 0.0358(8) 0.0235(7) 0.0303(7) -0.0037(6) -0.0021(6) -0.0082(6) C16 0.0358(8) 0.0291(8) 0.0375(8) 0.0016(6) -0.0044(7) -0.0136(6) C17 0.0254(8) 0.0446(9) 0.0349(8) -0.0031(7) 0.0036(6) -0.0078(7) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. anes) are estimated using the full covariance matrix. The cell esds are ken into account individually in the estimation of esds in distances, gles and torsion angles; correlations between esds in cell parameters are ly used when they are defined by crystal symmetry. An approximate sotropic) treatment of cell esds is used for estimating esds involving l.s. anes. ; 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 N1 C13 1.379(2) . ? N1 C1 1.412(2) . ? N1 C14 1.422(2) . ? O1 C7 1.373(2) . ? O1 C6 1.390(2) . ? O2 C7 1.198(2) . ? O3 C11 1.223(2) . ? O4 C14 1.205(2) . ? C1 C6 1.359(2) . ? C1 C2 1.495(2) . ? C2 C3 1.540(2) . ? C3 C4 1.521(2) . ? C3 C5 1.521(2) . ? C6 C12 1.439(2) . ? C7 C8 1.499(2) . ? C8 C9 1.552(2) . ? C9 C17 1.531(2) . ? C9 C16 1.531(2) . ? C9 C10 1.549(2) . ? C10 C11 1.507(2) . ? C11 C12 1.473(2) . ? C12 C13 1.367(2) . ? C14 C15 1.491(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 C13 N1 C1 109.32(11) . . ? C13 N1 C14 124.08(12) . . ? C1 N1 C14 126.46(12) . . ? C7 O1 C6 122.48(10) . . ? C6 C1 N1 105.59(12) . . ? C6 C1 C2 128.17(13) . . ? N1 C1 C2 126.23(12) . . ? C1 C2 C3 115.06(11) . . ? C4 C3 C5 111.1(2) . . ? C4 C3 C2 111.21(13) . . ? C5 C3 C2 109.82(12) . . ? C1 C6 O1 121.29(12) . . ? C1 C6 C12 110.36(12) . . ? O1 C6 C12 127.92(12) . . ? O2 C7 O1 116.81(12) . . ? O2 C7 C8 125.10(12) . . ? O1 C7 C8 118.01(11) . . ? C7 C8 C9 111.55(11) . . ? C17 C9 C16 109.59(12) . . ? C17 C9 C10 110.19(12) . . ? C16 C9 C10 107.41(11) . . ? C17 C9 C8 107.63(11) . . ? C16 C9 C8 109.91(12) . . ? C10 C9 C8 112.10(11) . . ? C11 C10 C9 115.75(11) . . ? O3 C11 C12 119.91(13) . . ? O3 C11 C10 120.43(13) . . ? C12 C11 C10 119.66(12) . . ? C13 C12 C6 105.46(12) . . ? C13 C12 C11 122.89(13) . . ? C6 C12 C11 131.64(12) . . ? C12 C13 N1 109.26(12) . . ? O4 C14 N1 119.44(14) . . ? O4 C14 C15 123.76(13) . . ? N1 C14 C15 116.81(12) . . ? _refine_diff_density_max .320 _refine_diff_density_min -.243 _refine_diff_density_rms .052