data_x1639l _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C14 H18 N2 O5' _chemical_formula_weight 294.30 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 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 11.439(2) _cell_length_b 11.760(2) _cell_length_c 10.777(2) _cell_angle_alpha 90.00 _cell_angle_beta 97.55(3) _cell_angle_gamma 90.00 _cell_volume 1437.2(5) _cell_formula_units_Z 4 _cell_measurement_temperature 100(2) _cell_measurement_reflns_used 2410 _cell_measurement_theta_min 2.99 _cell_measurement_theta_max 27.48 _exptl_crystal_description ? _exptl_crystal_colour ? _exptl_crystal_size_max 0.25 _exptl_crystal_size_mid 0.15 _exptl_crystal_size_min 0.05 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.360 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 624 _exptl_absorpt_coefficient_mu 0.104 _exptl_absorpt_correction_type none _exptl_absorpt_correction_T_min 0.9744 _exptl_absorpt_correction_T_max 0.9948 _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 100(2) _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-Nonius KappaCCD' _diffrn_measurement_method '\w scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 5290 _diffrn_reflns_av_R_equivalents 0.0354 _diffrn_reflns_av_sigmaI/netI 0.0547 _diffrn_reflns_limit_h_min -14 _diffrn_reflns_limit_h_max 14 _diffrn_reflns_limit_k_min -12 _diffrn_reflns_limit_k_max 15 _diffrn_reflns_limit_l_min -13 _diffrn_reflns_limit_l_max 13 _diffrn_reflns_theta_min 2.99 _diffrn_reflns_theta_max 27.48 _reflns_number_total 3282 _reflns_number_gt 2410 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker XSCANS' _computing_cell_refinement 'Bruker XSCANS' _computing_data_reduction 'Bruker SHELXTL' _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^)+(0.0463P)^2^+0.5416P] 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 ? _refine_ls_number_reflns 3282 _refine_ls_number_parameters 191 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0743 _refine_ls_R_factor_gt 0.0487 _refine_ls_wR_factor_ref 0.1171 _refine_ls_wR_factor_gt 0.1048 _refine_ls_goodness_of_fit_ref 1.039 _refine_ls_restrained_S_all 1.039 _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 O7 O 0.59515(10) 0.22576(10) 0.39433(10) 0.0232(3) Uani 1 1 d . . . O11 O 0.47920(11) 0.34073(10) 0.53337(11) 0.0237(3) Uani 1 1 d . . . H11A H 0.5120 0.2947 0.4894 0.036 Uiso 1 1 calc R . . O10 O 0.41285(10) 0.18056(10) 0.61203(10) 0.0216(3) Uani 1 1 d . . . O13 O 0.17603(11) 0.22691(10) 0.96008(11) 0.0255(3) Uani 1 1 d . . . O14 O 0.12616(12) 0.39440(11) 1.01774(12) 0.0308(3) Uani 1 1 d . . . N1 N 0.65950(12) 0.05554(12) 0.33382(12) 0.0191(3) Uani 1 1 d . . . H1A H 0.6559 -0.0188 0.3423 0.023 Uiso 1 1 calc R . . N13 N 0.17638(12) 0.33093(12) 0.95168(12) 0.0202(3) Uani 1 1 d . . . C1 C 0.73753(14) 0.10313(14) 0.24877(14) 0.0175(3) Uani 1 1 d . . . H1B H 0.6928 0.1636 0.1973 0.021 Uiso 1 1 calc R . . C2 C 0.84775(15) 0.15770(15) 0.31954(15) 0.0213(4) Uani 1 1 d . . . H2A H 0.8936 0.0999 0.3722 0.026 Uiso 1 1 calc R . . H2B H 0.8248 0.2186 0.3750 0.026 Uiso 1 1 calc R . . C3 C 0.92347(16) 0.20765(15) 0.22623(16) 0.0246(4) Uani 1 1 d . . . H3A H 0.8794 0.2694 0.1783 0.030 Uiso 1 1 calc R . . H3B H 0.9961 0.2408 0.2724 0.030 Uiso 1 1 calc R . . C4 C 0.95682(16) 0.11751(16) 0.13599(17) 0.0284(4) Uani 1 1 d . . . H4A H 1.0078 0.0597 0.1828 0.034 Uiso 1 1 calc R . . H4B H 1.0020 0.1532 0.0740 0.034 Uiso 1 1 calc R . . C5 C 0.84693(16) 0.06012(16) 0.06804(16) 0.0267(4) Uani 1 1 d . . . H5A H 0.8709 -0.0018 0.0145 0.032 Uiso 1 1 calc R . . H5B H 0.8009 0.1162 0.0132 0.032 Uiso 1 1 calc R . . C6 C 0.76966(15) 0.01125(15) 0.16046(15) 0.0214(4) Uani 1 1 d . . . H6A H 0.6969 -0.0211 0.1139 0.026 Uiso 1 1 calc R . . H6B H 0.8125 -0.0507 0.2093 0.026 Uiso 1 1 calc R . . C7 C 0.59503(14) 0.12017(14) 0.39759(15) 0.0195(4) Uani 1 1 d . . . H7A H 0.5452 0.0839 0.4494 0.023 Uiso 1 1 calc R . . C10 C 0.41894(14) 0.28414(14) 0.60890(14) 0.0180(3) Uani 1 1 d . . . C11 C 0.35897(14) 0.36046(14) 0.69175(14) 0.0172(3) Uani 1 1 d . . . C12 C 0.29579(14) 0.31142(14) 0.77998(14) 0.0181(4) Uani 1 1 d . . . H12A H 0.2904 0.2311 0.7873 0.022 Uiso 1 1 calc R . . C13 C 0.24134(14) 0.38242(14) 0.85642(14) 0.0187(4) Uani 1 1 d . . . C14 C 0.24556(15) 0.49982(15) 0.84846(15) 0.0214(4) Uani 1 1 d . . . H14A H 0.2058 0.5464 0.9015 0.026 Uiso 1 1 calc R . . C15 C 0.30947(15) 0.54752(14) 0.76081(15) 0.0224(4) Uani 1 1 d . . . H15A H 0.3144 0.6279 0.7538 0.027 Uiso 1 1 calc R . . C16 C 0.36620(15) 0.47818(14) 0.68331(15) 0.0200(4) Uani 1 1 d . . . H16A H 0.4104 0.5114 0.6240 0.024 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 O7 0.0263(7) 0.0185(7) 0.0265(6) 0.0014(5) 0.0106(5) 0.0014(5) O11 0.0272(7) 0.0186(6) 0.0279(6) -0.0009(5) 0.0131(5) 0.0002(5) O10 0.0259(7) 0.0152(6) 0.0245(6) -0.0006(5) 0.0060(5) 0.0002(5) O13 0.0331(7) 0.0175(7) 0.0276(6) 0.0004(5) 0.0100(5) -0.0027(5) O14 0.0357(8) 0.0270(7) 0.0331(7) -0.0067(6) 0.0175(6) 0.0003(6) N1 0.0216(7) 0.0155(7) 0.0211(7) 0.0016(6) 0.0054(6) -0.0004(6) N13 0.0208(7) 0.0197(8) 0.0203(7) -0.0026(6) 0.0041(6) -0.0005(6) C1 0.0187(8) 0.0163(8) 0.0180(8) 0.0015(6) 0.0045(6) -0.0007(6) C2 0.0218(9) 0.0197(9) 0.0225(8) -0.0013(7) 0.0033(7) -0.0009(7) C3 0.0210(9) 0.0214(9) 0.0320(9) 0.0004(7) 0.0058(7) -0.0014(7) C4 0.0259(10) 0.0258(10) 0.0365(10) 0.0036(8) 0.0149(8) 0.0005(8) C5 0.0341(10) 0.0235(10) 0.0250(9) -0.0010(7) 0.0126(7) 0.0021(8) C6 0.0255(9) 0.0172(9) 0.0221(8) -0.0012(7) 0.0054(7) -0.0004(7) C7 0.0196(9) 0.0207(9) 0.0191(8) 0.0024(7) 0.0056(6) -0.0011(7) C10 0.0173(8) 0.0184(9) 0.0182(8) 0.0005(7) 0.0014(6) -0.0009(7) C11 0.0160(8) 0.0184(9) 0.0168(7) -0.0003(6) 0.0002(6) -0.0001(6) C12 0.0186(8) 0.0148(8) 0.0205(8) 0.0003(6) 0.0012(6) -0.0003(6) C13 0.0191(8) 0.0206(9) 0.0159(7) 0.0002(7) 0.0007(6) -0.0025(7) C14 0.0244(9) 0.0192(9) 0.0201(8) -0.0024(7) 0.0009(7) 0.0021(7) C15 0.0291(9) 0.0147(8) 0.0229(8) 0.0004(7) 0.0019(7) 0.0008(7) C16 0.0226(9) 0.0181(9) 0.0190(8) 0.0030(7) 0.0016(6) -0.0010(7) _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 O7 C7 1.242(2) . ? O11 C10 1.315(2) . ? O10 C10 1.221(2) . ? O13 N13 1.2266(18) . ? O14 N13 1.2254(18) . ? N1 C7 1.314(2) . ? N1 C1 1.471(2) . ? N13 C13 1.474(2) . ? C1 C6 1.517(2) . ? C1 C2 1.527(2) . ? C2 C3 1.528(2) . ? C3 C4 1.521(3) . ? C4 C5 1.526(3) . ? C5 C6 1.528(2) . ? C10 C11 1.495(2) . ? C11 C16 1.390(2) . ? C11 C12 1.393(2) . ? C12 C13 1.378(2) . ? C13 C14 1.384(2) . ? C14 C15 1.387(2) . ? C15 C16 1.388(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 C7 N1 C1 122.26(14) . . ? O14 N13 O13 123.93(14) . . ? O14 N13 C13 118.16(14) . . ? O13 N13 C13 117.90(13) . . ? N1 C1 C6 109.68(13) . . ? N1 C1 C2 112.18(13) . . ? C6 C1 C2 111.14(14) . . ? C1 C2 C3 109.58(13) . . ? C4 C3 C2 111.37(14) . . ? C3 C4 C5 110.80(15) . . ? C4 C5 C6 111.35(14) . . ? C1 C6 C5 110.47(14) . . ? O7 C7 N1 124.10(16) . . ? O10 C10 O11 123.97(15) . . ? O10 C10 C11 123.39(15) . . ? O11 C10 C11 112.64(14) . . ? C16 C11 C12 119.84(15) . . ? C16 C11 C10 121.52(15) . . ? C12 C11 C10 118.63(15) . . ? C13 C12 C11 118.23(15) . . ? C12 C13 C14 123.03(16) . . ? C12 C13 N13 118.44(15) . . ? C14 C13 N13 118.53(15) . . ? C13 C14 C15 118.13(16) . . ? C14 C15 C16 120.15(16) . . ? C15 C16 C11 120.60(16) . . ? _diffrn_measured_fraction_theta_max 0.996 _diffrn_reflns_theta_full 27.48 _diffrn_measured_fraction_theta_full 0.996 _refine_diff_density_max 0.228 _refine_diff_density_min -0.332 _refine_diff_density_rms 0.051