data_datos_m _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C14 H13 N O5' _chemical_formula_weight 275.25 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)/c loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y-1/2, z-1/2' _cell_length_a 7.58380(10) _cell_length_b 17.6558(6) _cell_length_c 9.6242(3) _cell_angle_alpha 90.00 _cell_angle_beta 98.371(2) _cell_angle_gamma 90.00 _cell_volume 1274.93(6) _cell_formula_units_Z 4 _cell_measurement_temperature 100(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description prism _exptl_crystal_colour colorless _exptl_crystal_size_max 0.35 _exptl_crystal_size_mid 0.30 _exptl_crystal_size_min 0.10 _exptl_crystal_density_meas 0 _exptl_crystal_density_diffrn 1.434 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 576 _exptl_absorpt_coefficient_mu 0.929 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 100(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_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 11510 _diffrn_reflns_av_R_equivalents 0.0404 _diffrn_reflns_av_sigmaI/netI 0.0279 _diffrn_reflns_limit_h_min -9 _diffrn_reflns_limit_h_max 8 _diffrn_reflns_limit_k_min -20 _diffrn_reflns_limit_k_max 21 _diffrn_reflns_limit_l_min -10 _diffrn_reflns_limit_l_max 11 _diffrn_reflns_theta_min 5.01 _diffrn_reflns_theta_max 71.07 _reflns_number_total 2376 _reflns_number_gt 2178 _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, 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^)+(0.0475P)^2^+0.3590P] 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 mixed _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 2376 _refine_ls_number_parameters 233 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0366 _refine_ls_R_factor_gt 0.0337 _refine_ls_wR_factor_ref 0.0912 _refine_ls_wR_factor_gt 0.0888 _refine_ls_goodness_of_fit_ref 1.064 _refine_ls_restrained_S_all 1.064 _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 0.64034(18) 0.27437(7) 0.76409(13) 0.0270(3) Uani 1 1 d . . . C2 C 0.47451(18) 0.23464(7) 0.79474(14) 0.0257(3) Uani 1 1 d . . . C3 C 0.32828(17) 0.28874(7) 0.82061(13) 0.0231(3) Uani 1 1 d . . . C4 C 0.29005(17) 0.35206(7) 0.71300(13) 0.0239(3) Uani 1 1 d . . . C5 C 0.4575(2) 0.38164(7) 0.66442(14) 0.0285(3) Uani 1 1 d . . . C6 C 0.61482(19) 0.34727(8) 0.68800(15) 0.0298(3) Uani 1 1 d . . . C7 C 0.1480(2) 0.33255(9) 0.59114(15) 0.0314(3) Uani 1 1 d . . . C8 C 0.30177(18) 0.40234(7) 0.93725(13) 0.0239(3) Uani 1 1 d . . . C9 C 0.16309(17) 0.41105(7) 1.03452(13) 0.0219(3) Uani 1 1 d . . . C10 C 0.20268(17) 0.45098(7) 1.15931(13) 0.0235(3) Uani 1 1 d . . . C11 C 0.07730(17) 0.45774(7) 1.25034(13) 0.0233(3) Uani 1 1 d . . . C12 C -0.08793(17) 0.42508(7) 1.21124(13) 0.0214(3) Uani 1 1 d . . . C13 C -0.13231(18) 0.38522(7) 1.08685(13) 0.0244(3) Uani 1 1 d . . . C14 C -0.00441(18) 0.37788(7) 0.99901(14) 0.0254(3) Uani 1 1 d . . . N1 N -0.22465(14) 0.43519(6) 1.30302(11) 0.0228(2) Uani 1 1 d . . . O1 O 0.78819(13) 0.24666(6) 0.79596(11) 0.0359(3) Uani 1 1 d . . . O2 O 0.38325(12) 0.32886(5) 0.94992(9) 0.0263(2) Uani 1 1 d . . . O3 O 0.21937(12) 0.41002(5) 0.79607(9) 0.0261(2) Uani 1 1 d . . . O4 O -0.17692(13) 0.45257(6) 1.42641(9) 0.0307(2) Uani 1 1 d . . . O5 O -0.38120(12) 0.42677(5) 1.25155(10) 0.0290(2) Uani 1 1 d . . . H1 H 0.214(2) 0.2623(8) 0.8252(15) 0.021(3) Uiso 1 1 d . . . H2A H 0.431(2) 0.2030(9) 0.7128(16) 0.027(4) Uiso 1 1 d . . . H2B H 0.504(2) 0.2011(9) 0.8753(18) 0.034(4) Uiso 1 1 d . . . H5 H 0.443(2) 0.4292(9) 0.6119(17) 0.032(4) Uiso 1 1 d . . . H6 H 0.720(2) 0.3680(10) 0.6568(17) 0.035(4) Uiso 1 1 d . . . H7A H 0.037(3) 0.3177(10) 0.6255(18) 0.040(5) Uiso 1 1 d . . . H7B H 0.127(2) 0.3770(11) 0.5274(19) 0.041(5) Uiso 1 1 d . . . H7C H 0.190(2) 0.2892(10) 0.5399(18) 0.039(4) Uiso 1 1 d . . . H8 H 0.399(2) 0.4400(8) 0.9611(14) 0.020(3) Uiso 1 1 d . . . H10 H 0.320(2) 0.4741(9) 1.1833(15) 0.025(4) Uiso 1 1 d . . . H11 H 0.101(2) 0.4842(9) 1.3335(17) 0.025(4) Uiso 1 1 d . . . H13 H -0.248(2) 0.3637(9) 1.0624(16) 0.026(4) Uiso 1 1 d . . . H14 H -0.030(2) 0.3494(10) 0.9117(19) 0.035(4) 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 C1 0.0279(7) 0.0277(7) 0.0249(7) -0.0103(5) 0.0027(5) 0.0014(5) C2 0.0314(7) 0.0218(6) 0.0235(7) -0.0008(5) 0.0031(5) 0.0035(5) C3 0.0261(7) 0.0225(6) 0.0212(6) -0.0004(5) 0.0050(5) 0.0002(5) C4 0.0292(7) 0.0215(6) 0.0219(6) -0.0008(5) 0.0065(5) 0.0048(5) C5 0.0384(8) 0.0236(6) 0.0248(7) 0.0001(5) 0.0092(6) 0.0003(5) C6 0.0300(7) 0.0304(7) 0.0309(7) -0.0046(5) 0.0108(6) -0.0043(6) C7 0.0334(8) 0.0360(7) 0.0241(7) -0.0011(6) 0.0013(6) 0.0065(6) C8 0.0276(7) 0.0215(6) 0.0230(7) -0.0005(5) 0.0048(5) 0.0020(5) C9 0.0250(6) 0.0184(6) 0.0226(6) 0.0008(4) 0.0038(5) 0.0023(5) C10 0.0213(6) 0.0228(6) 0.0257(7) -0.0014(5) 0.0014(5) 0.0003(5) C11 0.0254(6) 0.0238(6) 0.0202(6) -0.0028(5) 0.0013(5) 0.0014(5) C12 0.0237(6) 0.0187(6) 0.0221(6) 0.0036(4) 0.0045(5) 0.0026(5) C13 0.0249(7) 0.0221(6) 0.0256(7) -0.0007(5) 0.0019(5) -0.0032(5) C14 0.0297(7) 0.0233(6) 0.0228(7) -0.0034(5) 0.0030(5) -0.0019(5) N1 0.0247(6) 0.0188(5) 0.0253(6) 0.0021(4) 0.0046(4) 0.0009(4) O1 0.0272(5) 0.0342(5) 0.0451(6) -0.0119(4) 0.0009(4) 0.0045(4) O2 0.0321(5) 0.0260(5) 0.0205(5) -0.0013(3) 0.0034(4) 0.0083(4) O3 0.0347(5) 0.0232(5) 0.0214(5) 0.0009(3) 0.0073(4) 0.0077(4) O4 0.0328(5) 0.0375(5) 0.0226(5) -0.0010(4) 0.0070(4) 0.0020(4) O5 0.0224(5) 0.0275(5) 0.0372(5) -0.0007(4) 0.0051(4) -0.0008(4) _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 O1 1.2208(17) . ? C1 C6 1.480(2) . ? C1 C2 1.5062(19) . ? C2 C3 1.5115(17) . ? C2 H2A 0.983(16) . ? C2 H2B 0.975(17) . ? C3 O2 1.4399(15) . ? C3 C4 1.5228(17) . ? C3 H1 0.989(15) . ? C4 O3 1.4486(14) . ? C4 C5 1.5091(19) . ? C4 C7 1.5120(19) . ? C5 C6 1.328(2) . ? C5 H5 0.978(17) . ? C6 H6 0.966(17) . ? C7 H7A 0.981(19) . ? C7 H7B 0.994(19) . ? C7 H7C 0.988(18) . ? C8 O3 1.4170(16) . ? C8 O2 1.4344(15) . ? C8 C9 1.5143(17) . ? C8 H8 0.994(15) . ? C9 C10 1.3873(18) . ? C9 C14 1.3953(18) . ? C10 C11 1.3887(18) . ? C10 H10 0.973(16) . ? C11 C12 1.3809(18) . ? C11 H11 0.922(16) . ? C12 C13 1.3873(18) . ? C12 N1 1.4676(16) . ? C13 C14 1.3825(19) . ? C13 H13 0.957(16) . ? C14 H14 0.974(18) . ? N1 O5 1.2271(14) . ? N1 O4 1.2289(14) . ? 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 O1 C1 C6 121.48(13) . . ? O1 C1 C2 121.78(12) . . ? C6 C1 C2 116.69(11) . . ? C1 C2 C3 113.05(11) . . ? C1 C2 H2A 107.5(9) . . ? C3 C2 H2A 108.7(9) . . ? C1 C2 H2B 109.9(10) . . ? C3 C2 H2B 109.9(10) . . ? H2A C2 H2B 107.6(13) . . ? O2 C3 C2 109.04(10) . . ? O2 C3 C4 103.25(10) . . ? C2 C3 C4 115.05(10) . . ? O2 C3 H1 109.8(8) . . ? C2 C3 H1 112.1(8) . . ? C4 C3 H1 107.2(8) . . ? O3 C4 C5 108.79(10) . . ? O3 C4 C7 108.06(10) . . ? C5 C4 C7 112.02(11) . . ? O3 C4 C3 101.09(9) . . ? C5 C4 C3 112.29(11) . . ? C7 C4 C3 113.82(11) . . ? C6 C5 C4 124.36(12) . . ? C6 C5 H5 120.7(10) . . ? C4 C5 H5 114.9(10) . . ? C5 C6 C1 122.11(13) . . ? C5 C6 H6 122.4(10) . . ? C1 C6 H6 115.5(10) . . ? C4 C7 H7A 110.3(10) . . ? C4 C7 H7B 109.2(11) . . ? H7A C7 H7B 110.7(14) . . ? C4 C7 H7C 108.5(10) . . ? H7A C7 H7C 108.4(15) . . ? H7B C7 H7C 109.7(14) . . ? O3 C8 O2 107.01(9) . . ? O3 C8 C9 109.52(10) . . ? O2 C8 C9 111.64(10) . . ? O3 C8 H8 111.5(8) . . ? O2 C8 H8 106.9(8) . . ? C9 C8 H8 110.3(8) . . ? C10 C9 C14 120.00(11) . . ? C10 C9 C8 120.30(11) . . ? C14 C9 C8 119.69(11) . . ? C9 C10 C11 120.53(12) . . ? C9 C10 H10 119.6(9) . . ? C11 C10 H10 119.9(9) . . ? C12 C11 C10 118.01(12) . . ? C12 C11 H11 120.3(9) . . ? C10 C11 H11 121.6(9) . . ? C11 C12 C13 122.93(12) . . ? C11 C12 N1 118.54(11) . . ? C13 C12 N1 118.50(11) . . ? C14 C13 C12 118.13(12) . . ? C14 C13 H13 121.0(9) . . ? C12 C13 H13 120.8(9) . . ? C13 C14 C9 120.38(12) . . ? C13 C14 H14 120.5(10) . . ? C9 C14 H14 119.1(10) . . ? O5 N1 O4 123.50(10) . . ? O5 N1 C12 117.98(10) . . ? O4 N1 C12 118.52(10) . . ? C8 O2 C3 107.73(9) . . ? C8 O3 C4 108.34(9) . . ? 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 C3 149.61(12) . . . . ? C6 C1 C2 C3 -32.89(15) . . . . ? C1 C2 C3 O2 -67.52(13) . . . . ? C1 C2 C3 C4 47.87(15) . . . . ? O2 C3 C4 O3 -34.76(12) . . . . ? C2 C3 C4 O3 -153.44(11) . . . . ? O2 C3 C4 C5 81.04(12) . . . . ? C2 C3 C4 C5 -37.64(15) . . . . ? O2 C3 C4 C7 -150.34(11) . . . . ? C2 C3 C4 C7 90.97(14) . . . . ? O3 C4 C5 C6 124.44(14) . . . . ? C7 C4 C5 C6 -116.17(15) . . . . ? C3 C4 C5 C6 13.39(18) . . . . ? C4 C5 C6 C1 1.0(2) . . . . ? O1 C1 C6 C5 -173.46(13) . . . . ? C2 C1 C6 C5 9.03(19) . . . . ? O3 C8 C9 C10 -139.91(11) . . . . ? O2 C8 C9 C10 101.77(13) . . . . ? O3 C8 C9 C14 40.91(15) . . . . ? O2 C8 C9 C14 -77.42(14) . . . . ? C14 C9 C10 C11 0.60(19) . . . . ? C8 C9 C10 C11 -178.59(11) . . . . ? C9 C10 C11 C12 -1.41(18) . . . . ? C10 C11 C12 C13 0.99(18) . . . . ? C10 C11 C12 N1 -176.86(10) . . . . ? C11 C12 C13 C14 0.26(19) . . . . ? N1 C12 C13 C14 178.11(11) . . . . ? C12 C13 C14 C9 -1.11(19) . . . . ? C10 C9 C14 C13 0.69(19) . . . . ? C8 C9 C14 C13 179.88(11) . . . . ? C11 C12 N1 O5 158.68(11) . . . . ? C13 C12 N1 O5 -19.27(16) . . . . ? C11 C12 N1 O4 -20.37(16) . . . . ? C13 C12 N1 O4 161.69(11) . . . . ? O3 C8 O2 C3 -7.77(13) . . . . ? C9 C8 O2 C3 112.04(11) . . . . ? C2 C3 O2 C8 149.46(10) . . . . ? C4 C3 O2 C8 26.67(12) . . . . ? O2 C8 O3 C4 -15.80(13) . . . . ? C9 C8 O3 C4 -136.97(10) . . . . ? C5 C4 O3 C8 -87.15(12) . . . . ? C7 C4 O3 C8 151.00(11) . . . . ? C3 C4 O3 C8 31.21(12) . . . . ? _diffrn_measured_fraction_theta_max 0.964 _diffrn_reflns_theta_full 71.07 _diffrn_measured_fraction_theta_full 0.964 _refine_diff_density_max 0.263 _refine_diff_density_min -0.206 _refine_diff_density_rms 0.041