data_p212121 _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C13 H10 N O4' _chemical_formula_weight 244.22 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 Orthorhombic _symmetry_space_group_name_H-M P2(1)2(1)2(1) loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, -y, z+1/2' '-x, y+1/2, -z+1/2' 'x+1/2, -y+1/2, -z' _cell_length_a 6.9340(2) _cell_length_b 9.6320(3) _cell_length_c 17.3308(5) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 1157.49(6) _cell_formula_units_Z 4 _cell_measurement_temperature 298 _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description plate _exptl_crystal_colour colorless _exptl_crystal_size_max 0.41 _exptl_crystal_size_mid 0.4 _exptl_crystal_size_min 0.3 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.401 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 508 _exptl_absorpt_coefficient_mu 0.106 _exptl_absorpt_correction_type MULTI-SCAN _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _exptl_absorpt_process_details SADABS _exptl_special_details ; ? ; _diffrn_ambient_temperature 298 _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 'omega and phi scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 6735 _diffrn_reflns_av_R_equivalents 0.0266 _diffrn_reflns_av_sigmaI/netI 0.0222 _diffrn_reflns_limit_h_min -9 _diffrn_reflns_limit_h_max 8 _diffrn_reflns_limit_k_min -12 _diffrn_reflns_limit_k_max 8 _diffrn_reflns_limit_l_min -21 _diffrn_reflns_limit_l_max 23 _diffrn_reflns_theta_min 2.35 _diffrn_reflns_theta_max 28.28 _reflns_number_total 2756 _reflns_number_gt 2474 _reflns_threshold_expression >2sigma(I) _computing_data_collection ? _computing_cell_refinement ? _computing_data_reduction ? _computing_structure_solution ? _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics ? _computing_publication_material ? _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^)+(0.0728P)^2^+0.1500P] 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_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _refine_ls_abs_structure_Flack 1.4(15) _refine_ls_number_reflns 2756 _refine_ls_number_parameters 163 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0557 _refine_ls_R_factor_gt 0.0508 _refine_ls_wR_factor_ref 0.1351 _refine_ls_wR_factor_gt 0.1298 _refine_ls_goodness_of_fit_ref 1.092 _refine_ls_restrained_S_all 1.092 _refine_ls_shift/su_max 0.002 _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 0.7328(4) 0.0056(3) 0.12764(13) 0.0646(6) Uani 1 1 d . . . H1 H 0.8355 -0.0513 0.1137 0.077 Uiso 1 1 calc R . . C2 C 0.5672(5) -0.0483(3) 0.16162(15) 0.0791(9) Uani 1 1 d . . . H2 H 0.5590 -0.1433 0.1706 0.095 Uiso 1 1 calc R . . C3 C 0.4155(5) 0.0355(4) 0.18226(14) 0.0819(9) Uani 1 1 d . . . H3 H 0.3059 -0.0043 0.2039 0.098 Uiso 1 1 calc R . . C4 C 0.4221(4) 0.1784(3) 0.17160(12) 0.0699(7) Uani 1 1 d . . . H4 H 0.3205 0.2355 0.1863 0.084 Uiso 1 1 calc R . . C5 C 0.5871(3) 0.2312(2) 0.13804(10) 0.0530(5) Uani 1 1 d . . . C6 C 0.7378(3) 0.1462(2) 0.11567(10) 0.0506(5) Uani 1 1 d . . . C7 C 0.8866(3) 0.2340(2) 0.07823(10) 0.0474(4) Uani 1 1 d . . . O2 O 1.0352(2) 0.20057(17) 0.04689(10) 0.0636(4) Uani 1 1 d . . . C8 C 0.6383(3) 0.3764(2) 0.11810(11) 0.0505(4) Uani 1 1 d . . . O1 O 0.5492(2) 0.48170(19) 0.12869(10) 0.0710(5) Uani 1 1 d . . . N1 N 0.8202(2) 0.37016(17) 0.08364(8) 0.0447(3) Uani 1 1 d . . . C9 C 0.9117(3) 0.4881(2) 0.04837(11) 0.0497(4) Uani 1 1 d . . . H9A H 0.8277 0.5681 0.0534 0.060 Uiso 1 1 calc R . . H9B H 0.9285 0.4698 -0.0063 0.060 Uiso 1 1 calc R . . C10 C 1.1069(3) 0.52262(19) 0.08355(11) 0.0455(4) Uani 1 1 d . . . C11 C 1.0982(3) 0.55325(19) 0.16930(11) 0.0506(4) Uani 1 1 d . . . H11A H 0.9897 0.5060 0.1929 0.061 Uiso 1 1 calc R . . H11B H 1.2158 0.5232 0.1946 0.061 Uiso 1 1 calc R . . C12 C 1.0753(4) 0.7067(2) 0.17558(12) 0.0581(5) Uani 1 1 d . . . O3 O 1.0293(4) 0.77583(19) 0.22960(10) 0.0932(7) Uani 1 1 d . . . O4 O 1.1206(3) 0.76553(16) 0.10717(10) 0.0739(5) Uani 1 1 d . . . C13 C 1.1812(4) 0.6619(2) 0.05279(14) 0.0624(5) Uani 1 1 d . . . H13A H 1.3207 0.6605 0.0487 0.075 Uiso 1 1 calc R . . H13B H 1.1274 0.6808 0.0022 0.075 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 C1 0.0764(15) 0.0656(13) 0.0518(11) 0.0050(11) -0.0159(10) -0.0084(11) C2 0.103(2) 0.0797(16) 0.0542(12) 0.0177(11) -0.0196(14) -0.0323(17) C3 0.0792(18) 0.115(2) 0.0519(12) 0.0087(13) 0.0016(12) -0.0432(18) C4 0.0550(12) 0.1040(19) 0.0507(11) -0.0076(12) 0.0059(9) -0.0233(12) C5 0.0439(10) 0.0755(13) 0.0394(8) -0.0075(8) -0.0006(8) -0.0078(9) C6 0.0501(10) 0.0643(11) 0.0374(8) 0.0000(8) -0.0085(7) -0.0066(9) C7 0.0441(9) 0.0607(10) 0.0376(8) -0.0046(7) -0.0025(7) 0.0022(8) O2 0.0525(8) 0.0708(9) 0.0675(8) -0.0041(7) 0.0132(7) 0.0108(7) C8 0.0350(8) 0.0705(12) 0.0459(9) -0.0112(9) -0.0023(7) 0.0007(9) O1 0.0484(8) 0.0806(10) 0.0841(11) -0.0191(9) 0.0061(7) 0.0130(8) N1 0.0351(7) 0.0561(9) 0.0429(7) -0.0053(7) -0.0008(6) 0.0004(7) C9 0.0485(9) 0.0581(10) 0.0424(8) 0.0038(8) -0.0030(8) 0.0042(9) C10 0.0442(9) 0.0436(8) 0.0489(9) 0.0007(7) 0.0001(8) 0.0009(7) C11 0.0551(11) 0.0474(9) 0.0492(9) 0.0020(8) -0.0034(9) -0.0029(8) C12 0.0637(13) 0.0511(10) 0.0595(11) -0.0040(9) -0.0050(10) 0.0075(10) O3 0.1342(19) 0.0721(11) 0.0734(11) -0.0233(9) -0.0019(13) 0.0253(13) O4 0.1025(14) 0.0447(7) 0.0745(10) 0.0051(7) 0.0064(10) -0.0046(9) C13 0.0634(13) 0.0591(12) 0.0647(12) 0.0061(10) 0.0125(10) -0.0097(10) _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 C6 1.371(3) . ? C1 C2 1.391(4) . ? C2 C3 1.373(5) . ? C3 C4 1.389(4) . ? C4 C5 1.381(3) . ? C5 C6 1.383(3) . ? C5 C8 1.484(3) . ? C6 C7 1.483(3) . ? C7 O2 1.209(2) . ? C7 N1 1.394(3) . ? C8 O1 1.201(3) . ? C8 N1 1.397(2) . ? N1 C9 1.438(3) . ? C9 C10 1.521(3) . ? C10 C11 1.516(3) . ? C10 C13 1.533(3) . ? C11 C12 1.491(3) . ? C12 O3 1.192(3) . ? C12 O4 1.351(3) . ? O4 C13 1.436(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 C6 C1 C2 117.0(3) . . ? C3 C2 C1 121.6(2) . . ? C2 C3 C4 121.5(3) . . ? C5 C4 C3 116.6(3) . . ? C4 C5 C6 121.8(2) . . ? C4 C5 C8 130.0(2) . . ? C6 C5 C8 108.20(18) . . ? C1 C6 C5 121.6(2) . . ? C1 C6 C7 130.3(2) . . ? C5 C6 C7 108.11(19) . . ? O2 C7 N1 124.26(19) . . ? O2 C7 C6 129.6(2) . . ? N1 C7 C6 106.09(16) . . ? O1 C8 N1 124.4(2) . . ? O1 C8 C5 129.61(18) . . ? N1 C8 C5 105.94(17) . . ? C7 N1 C8 111.59(16) . . ? C7 N1 C9 124.68(15) . . ? C8 N1 C9 123.13(17) . . ? N1 C9 C10 113.28(15) . . ? C11 C10 C9 113.58(16) . . ? C11 C10 C13 100.60(16) . . ? C9 C10 C13 110.56(16) . . ? C12 C11 C10 105.59(16) . . ? O3 C12 O4 121.2(2) . . ? O3 C12 C11 129.8(2) . . ? O4 C12 C11 109.08(17) . . ? C12 O4 C13 110.63(16) . . ? O4 C13 C10 106.36(17) . . ? _diffrn_measured_fraction_theta_max 0.997 _diffrn_reflns_theta_full 28.28 _diffrn_measured_fraction_theta_full 0.997 _refine_diff_density_max 0.406 _refine_diff_density_min -0.366 _refine_diff_density_rms 0.087