data_lcw07 _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C16 H14 N2 O5' _chemical_formula_sum 'C16 H14 N2 O5' _chemical_formula_weight 314.29 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 trilinic _symmetry_space_group_name_H-M 'P -1' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 8.595(2) _cell_length_b 9.799(3) _cell_length_c 10.014(3) _cell_angle_alpha 71.928(5) _cell_angle_beta 85.027(5) _cell_angle_gamma 68.533(5) _cell_volume 745.9(3) _cell_formula_units_Z 2 _cell_measurement_temperature 193(2) _cell_measurement_reflns_used 954 _cell_measurement_theta_min 2.55 _cell_measurement_theta_max 23.75 _exptl_crystal_description block _exptl_crystal_colour yellow _exptl_crystal_size_max 0.16 _exptl_crystal_size_mid 0.12 _exptl_crystal_size_min 0.09 _exptl_crystal_density_meas 'not measured' _exptl_crystal_density_diffrn 1.399 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 328 _exptl_absorpt_coefficient_mu 0.106 _exptl_absorpt_correction_type 'multi-scan (SADABS)' _exptl_absorpt_correction_T_min 0.9833 _exptl_absorpt_correction_T_max 0.9905 _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 193(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 '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 5715 _diffrn_reflns_av_R_equivalents 0.0241 _diffrn_reflns_av_sigmaI/netI 0.0507 _diffrn_reflns_limit_h_min -11 _diffrn_reflns_limit_h_max 8 _diffrn_reflns_limit_k_min -13 _diffrn_reflns_limit_k_max 13 _diffrn_reflns_limit_l_min -13 _diffrn_reflns_limit_l_max 13 _diffrn_reflns_theta_min 2.14 _diffrn_reflns_theta_max 28.38 _reflns_number_total 3706 _reflns_number_gt 2360 _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^)+(0.0520P)^2^+0.0133P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens difmap _refine_ls_hydrogen_treatment refall _refine_ls_extinction_method none _refine_ls_extinction_coef noref _refine_ls_number_reflns 3706 _refine_ls_number_parameters 264 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0898 _refine_ls_R_factor_gt 0.0510 _refine_ls_wR_factor_ref 0.1220 _refine_ls_wR_factor_gt 0.1048 _refine_ls_goodness_of_fit_ref 1.016 _refine_ls_restrained_S_all 1.016 _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 0.17369(15) 0.56413(13) 0.49446(12) 0.0346(3) Uani 1 1 d . . . O2 O 0.39387(16) 0.53824(14) 0.35451(13) 0.0385(3) Uani 1 1 d . . . O3 O -0.17079(19) 1.03227(17) -0.11040(16) 0.0596(4) Uani 1 1 d . . . O4 O -0.02019(19) 0.92494(16) -0.26095(15) 0.0562(4) Uani 1 1 d . . . O5 O 0.32818(16) 0.39720(14) 0.03698(12) 0.0379(3) Uani 1 1 d . . . N1 N 0.18720(18) 0.36211(16) 0.28947(14) 0.0311(3) Uani 1 1 d . . . N2 N -0.0696(2) 0.92087(19) -0.14157(18) 0.0434(4) Uani 1 1 d . . . C1 C 0.2546(2) 0.35779(19) 0.40028(17) 0.0271(4) Uani 1 1 d . . . C2 C 0.3142(2) 0.21710(18) 0.52029(17) 0.0271(4) Uani 1 1 d . . . C3 C 0.2748(2) 0.0894(2) 0.5276(2) 0.0328(4) Uani 1 1 d . . . H3 H 0.206(2) 0.096(2) 0.459(2) 0.037(5) Uiso 1 1 d . . . C4 C 0.3346(3) -0.0426(2) 0.6390(2) 0.0401(5) Uani 1 1 d . . . H4 H 0.310(2) -0.131(2) 0.6415(19) 0.039(5) Uiso 1 1 d . . . C5 C 0.4352(3) -0.0503(2) 0.7431(2) 0.0419(5) Uani 1 1 d . . . H5 H 0.480(3) -0.143(3) 0.819(2) 0.058(6) Uiso 1 1 d . . . C6 C 0.4747(2) 0.0754(2) 0.7368(2) 0.0388(5) Uani 1 1 d . . . H6 H 0.546(2) 0.071(2) 0.810(2) 0.049(6) Uiso 1 1 d . . . C7 C 0.4143(2) 0.2086(2) 0.62654(18) 0.0322(4) Uani 1 1 d . . . H7 H 0.445(2) 0.295(2) 0.6202(18) 0.033(5) Uiso 1 1 d . . . C8 C 0.2839(2) 0.49672(19) 0.41192(17) 0.0273(4) Uani 1 1 d . . . C9 C 0.1886(3) 0.7004(2) 0.5123(3) 0.0437(5) Uani 1 1 d . . . H9A H 0.301(3) 0.682(2) 0.544(2) 0.048(6) Uiso 1 1 d . . . H9B H 0.100(3) 0.733(2) 0.579(2) 0.044(5) Uiso 1 1 d . . . H9C H 0.171(3) 0.778(3) 0.424(2) 0.058(7) Uiso 1 1 d . . . C10 C 0.1243(2) 0.50447(19) 0.18278(17) 0.0294(4) Uani 1 1 d . . . C11 C -0.0111(2) 0.6247(2) 0.2049(2) 0.0362(4) Uani 1 1 d . . . H11 H -0.062(2) 0.613(2) 0.295(2) 0.039(5) Uiso 1 1 d . . . C12 C -0.0756(2) 0.7621(2) 0.0998(2) 0.0377(5) Uani 1 1 d . . . H12 H -0.167(2) 0.847(2) 0.1127(19) 0.048(6) Uiso 1 1 d . . . C13 C -0.0044(2) 0.7752(2) -0.02877(19) 0.0336(4) Uani 1 1 d . . . C14 C 0.1296(2) 0.6565(2) -0.05652(19) 0.0335(4) Uani 1 1 d . . . H14 H 0.171(2) 0.6747(19) -0.1479(19) 0.032(5) Uiso 1 1 d . . . C15 C 0.1945(2) 0.5204(2) 0.04938(17) 0.0296(4) Uani 1 1 d . . . C16 C 0.4072(3) 0.4118(3) -0.0960(2) 0.0432(5) Uani 1 1 d . . . H16A H 0.502(3) 0.316(2) -0.085(2) 0.053(6) Uiso 1 1 d . . . H16B H 0.450(2) 0.500(2) -0.118(2) 0.050(6) Uiso 1 1 d . . . H16C H 0.330(3) 0.424(2) -0.169(2) 0.052(6) 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 O1 0.0374(7) 0.0317(7) 0.0380(7) -0.0166(6) 0.0098(6) -0.0129(6) O2 0.0423(8) 0.0425(7) 0.0376(7) -0.0133(6) 0.0112(6) -0.0241(6) O3 0.0507(9) 0.0390(8) 0.0701(11) -0.0069(8) -0.0083(8) -0.0002(7) O4 0.0616(10) 0.0540(9) 0.0382(8) 0.0056(7) -0.0009(7) -0.0195(8) O5 0.0411(8) 0.0370(7) 0.0289(7) -0.0105(6) 0.0085(6) -0.0075(6) N1 0.0344(8) 0.0342(8) 0.0265(8) -0.0099(6) 0.0058(6) -0.0146(7) N2 0.0361(10) 0.0403(10) 0.0479(11) -0.0021(8) -0.0078(8) -0.0142(8) C1 0.0254(9) 0.0313(9) 0.0264(9) -0.0115(7) 0.0090(7) -0.0115(7) C2 0.0252(9) 0.0285(9) 0.0278(9) -0.0119(7) 0.0080(7) -0.0084(7) C3 0.0315(10) 0.0339(10) 0.0351(10) -0.0136(8) 0.0065(8) -0.0125(8) C4 0.0471(12) 0.0262(10) 0.0460(12) -0.0111(9) 0.0100(10) -0.0135(9) C5 0.0451(12) 0.0312(10) 0.0355(11) -0.0060(9) 0.0034(9) -0.0017(9) C6 0.0350(11) 0.0423(11) 0.0331(10) -0.0129(9) 0.0006(9) -0.0057(9) C7 0.0337(10) 0.0322(10) 0.0327(10) -0.0133(8) 0.0065(8) -0.0120(8) C8 0.0289(9) 0.0292(9) 0.0214(8) -0.0046(7) 0.0020(7) -0.0103(8) C9 0.0465(14) 0.0338(11) 0.0542(14) -0.0220(11) 0.0032(12) -0.0113(10) C10 0.0319(10) 0.0342(9) 0.0254(9) -0.0090(8) 0.0007(7) -0.0153(8) C11 0.0321(10) 0.0441(11) 0.0316(10) -0.0116(9) 0.0067(8) -0.0139(9) C12 0.0282(10) 0.0398(11) 0.0422(11) -0.0139(9) 0.0026(9) -0.0079(9) C13 0.0304(10) 0.0351(10) 0.0341(10) -0.0055(8) -0.0041(8) -0.0131(8) C14 0.0353(10) 0.0409(11) 0.0273(10) -0.0086(8) 0.0036(8) -0.0189(9) C15 0.0294(9) 0.0340(9) 0.0275(9) -0.0115(8) 0.0012(7) -0.0120(8) C16 0.0453(13) 0.0503(13) 0.0324(11) -0.0178(10) 0.0115(10) -0.0132(11) _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 C8 1.3276(19) . ? O1 C9 1.452(2) . ? O2 C8 1.196(2) . ? O3 N2 1.231(2) . ? O4 N2 1.227(2) . ? O5 C15 1.359(2) . ? O5 C16 1.432(2) . ? N1 C1 1.278(2) . ? N1 C10 1.415(2) . ? N2 C13 1.467(2) . ? C1 C2 1.473(2) . ? C1 C8 1.512(2) . ? C2 C7 1.390(2) . ? C2 C3 1.391(2) . ? C3 C4 1.378(3) . ? C3 H3 0.918(19) . ? C4 C5 1.378(3) . ? C4 H4 0.954(19) . ? C5 C6 1.375(3) . ? C5 H5 0.96(2) . ? C6 C7 1.379(3) . ? C6 H6 0.98(2) . ? C7 H7 0.956(18) . ? C9 H9A 0.98(2) . ? C9 H9B 0.996(19) . ? C9 H9C 0.95(2) . ? C10 C11 1.380(2) . ? C10 C15 1.405(2) . ? C11 C12 1.380(3) . ? C11 H11 0.956(19) . ? C12 C13 1.366(3) . ? C12 H12 0.949(19) . ? C13 C14 1.386(2) . ? C14 C15 1.376(2) . ? C14 H14 0.941(18) . ? C16 H16A 0.98(2) . ? C16 H16B 1.01(2) . ? C16 H16C 0.99(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 C8 O1 C9 116.16(15) . . ? C15 O5 C16 117.08(15) . . ? C1 N1 C10 118.58(14) . . ? O4 N2 O3 123.85(17) . . ? O4 N2 C13 118.39(17) . . ? O3 N2 C13 117.76(17) . . ? N1 C1 C2 122.37(15) . . ? N1 C1 C8 121.16(15) . . ? C2 C1 C8 116.42(15) . . ? C7 C2 C3 118.90(17) . . ? C7 C2 C1 120.37(15) . . ? C3 C2 C1 120.71(16) . . ? C4 C3 C2 120.00(19) . . ? C4 C3 H3 121.0(12) . . ? C2 C3 H3 118.9(12) . . ? C5 C4 C3 120.65(19) . . ? C5 C4 H4 119.9(11) . . ? C3 C4 H4 119.4(12) . . ? C6 C5 C4 119.73(19) . . ? C6 C5 H5 119.4(13) . . ? C4 C5 H5 120.8(13) . . ? C5 C6 C7 120.2(2) . . ? C5 C6 H6 120.3(12) . . ? C7 C6 H6 119.5(12) . . ? C6 C7 C2 120.50(18) . . ? C6 C7 H7 120.3(11) . . ? C2 C7 H7 119.2(11) . . ? O2 C8 O1 125.09(16) . . ? O2 C8 C1 123.67(15) . . ? O1 C8 C1 111.23(14) . . ? O1 C9 H9A 112.3(12) . . ? O1 C9 H9B 105.1(11) . . ? H9A C9 H9B 113.6(16) . . ? O1 C9 H9C 109.5(13) . . ? H9A C9 H9C 105.0(18) . . ? H9B C9 H9C 111.4(16) . . ? C11 C10 C15 119.41(16) . . ? C11 C10 N1 121.18(15) . . ? C15 C10 N1 119.30(15) . . ? C10 C11 C12 121.28(17) . . ? C10 C11 H11 119.8(11) . . ? C12 C11 H11 119.0(11) . . ? C13 C12 C11 118.17(18) . . ? C13 C12 H12 118.8(12) . . ? C11 C12 H12 123.0(12) . . ? C12 C13 C14 122.52(17) . . ? C12 C13 N2 119.09(17) . . ? C14 C13 N2 118.38(16) . . ? C15 C14 C13 118.94(17) . . ? C15 C14 H14 123.8(10) . . ? C13 C14 H14 117.2(10) . . ? O5 C15 C14 124.72(15) . . ? O5 C15 C10 115.59(15) . . ? C14 C15 C10 119.66(16) . . ? O5 C16 H16A 106.0(12) . . ? O5 C16 H16B 109.2(11) . . ? H16A C16 H16B 109.2(16) . . ? O5 C16 H16C 110.3(12) . . ? H16A C16 H16C 108.9(16) . . ? H16B C16 H16C 113.1(17) . . ? 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 C10 N1 C1 C2 176.19(14) . . . . ? C10 N1 C1 C8 -6.5(2) . . . . ? N1 C1 C2 C7 167.75(16) . . . . ? C8 C1 C2 C7 -9.7(2) . . . . ? N1 C1 C2 C3 -10.6(2) . . . . ? C8 C1 C2 C3 171.92(15) . . . . ? C7 C2 C3 C4 0.2(2) . . . . ? C1 C2 C3 C4 178.58(15) . . . . ? C2 C3 C4 C5 -0.9(3) . . . . ? C3 C4 C5 C6 0.9(3) . . . . ? C4 C5 C6 C7 -0.3(3) . . . . ? C5 C6 C7 C2 -0.4(3) . . . . ? C3 C2 C7 C6 0.5(2) . . . . ? C1 C2 C7 C6 -177.95(15) . . . . ? C9 O1 C8 O2 1.3(3) . . . . ? C9 O1 C8 C1 -179.37(16) . . . . ? N1 C1 C8 O2 -75.9(2) . . . . ? C2 C1 C8 O2 101.57(19) . . . . ? N1 C1 C8 O1 104.73(17) . . . . ? C2 C1 C8 O1 -77.80(18) . . . . ? C1 N1 C10 C11 -66.5(2) . . . . ? C1 N1 C10 C15 117.43(18) . . . . ? C15 C10 C11 C12 -2.1(3) . . . . ? N1 C10 C11 C12 -178.15(17) . . . . ? C10 C11 C12 C13 1.6(3) . . . . ? C11 C12 C13 C14 -0.4(3) . . . . ? C11 C12 C13 N2 -179.23(17) . . . . ? O4 N2 C13 C12 -170.46(18) . . . . ? O3 N2 C13 C12 9.7(3) . . . . ? O4 N2 C13 C14 10.6(3) . . . . ? O3 N2 C13 C14 -169.19(16) . . . . ? C12 C13 C14 C15 -0.4(3) . . . . ? N2 C13 C14 C15 178.50(16) . . . . ? C16 O5 C15 C14 0.6(3) . . . . ? C16 O5 C15 C10 -177.48(17) . . . . ? C13 C14 C15 O5 -178.08(16) . . . . ? C13 C14 C15 C10 -0.1(3) . . . . ? C11 C10 C15 O5 179.44(15) . . . . ? N1 C10 C15 O5 -4.4(2) . . . . ? C11 C10 C15 C14 1.3(3) . . . . ? N1 C10 C15 C14 177.44(16) . . . . ? _diffrn_measured_fraction_theta_max 0.991 _diffrn_reflns_theta_full 28.38 _diffrn_measured_fraction_theta_full 0.991 _refine_diff_density_max 0.193 _refine_diff_density_min -0.225 _refine_diff_density_rms 0.044