data_281211d_0m _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ' C16 H12 N4 O4' _chemical_formula_sum 'C16 H12 N4 O4' _chemical_formula_weight 324.30 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' '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' 'H' 'H' 0.0000 0.0000 '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' _symmetry_space_group_name_Hall '-P 1' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 7.8700(14) _cell_length_b 8.0484(15) _cell_length_c 11.469(2) _cell_angle_alpha 94.770(2) _cell_angle_beta 92.856(3) _cell_angle_gamma 95.972(2) _cell_volume 718.8(2) _cell_formula_units_Z 2 _cell_measurement_temperature 291(2) _cell_measurement_reflns_used 824 _cell_measurement_theta_min 2.555 _cell_measurement_theta_max 26.806 _exptl_crystal_description block _exptl_crystal_colour yellow _exptl_crystal_size_max 0.12 _exptl_crystal_size_mid 0.10 _exptl_crystal_size_min 0.10 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.498 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 336 _exptl_absorpt_coefficient_mu 0.111 _exptl_absorpt_correction_type 'Multi-scan' _exptl_absorpt_correction_T_min 0.9838 _exptl_absorpt_correction_T_max 0.9895 _exptl_absorpt_process_details 'SADABS, Bruker(2000)' _exptl_special_details ; ? ; _diffrn_ambient_temperature 291(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 CCD area detector' _diffrn_measurement_method '\f and \w scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number 0 _diffrn_standards_interval_count 0 _diffrn_standards_interval_time 0 _diffrn_standards_decay_% 0 _diffrn_reflns_number 3625 _diffrn_reflns_av_R_equivalents 0.0239 _diffrn_reflns_av_sigmaI/netI 0.0425 _diffrn_reflns_limit_h_min -8 _diffrn_reflns_limit_h_max 9 _diffrn_reflns_limit_k_min -9 _diffrn_reflns_limit_k_max 9 _diffrn_reflns_limit_l_min -9 _diffrn_reflns_limit_l_max 13 _diffrn_reflns_theta_min 2.55 _diffrn_reflns_theta_max 24.98 _reflns_number_total 2499 _reflns_number_gt 1199 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'SMART (BRUKER 2000)' _computing_cell_refinement SMART _computing_data_reduction 'SAINT (BRUKER 2000)' _computing_structure_solution 'SHELXTL (BRUKER 2000)' _computing_structure_refinement SHELXTL _computing_molecular_graphics SHELXTL _computing_publication_material 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^)+(0.0630P)^2^] 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 2499 _refine_ls_number_parameters 218 _refine_ls_number_restraints 2 _refine_ls_R_factor_all 0.1019 _refine_ls_R_factor_gt 0.0440 _refine_ls_wR_factor_ref 0.1375 _refine_ls_wR_factor_gt 0.1222 _refine_ls_goodness_of_fit_ref 0.941 _refine_ls_restrained_S_all 0.943 _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 0.8450(3) 0.4096(3) 0.5882(2) 0.0559(6) Uani 1 1 d U . . C2 C 0.8268(3) 0.5840(3) 0.6294(2) 0.0595(6) Uani 1 1 d . . . C3 C 0.6781(3) 0.6171(3) 0.4431(2) 0.0570(6) Uani 1 1 d . . . C4 C 0.6902(3) 0.4499(3) 0.4010(2) 0.0568(6) Uani 1 1 d . . . C5 C 0.7729(3) 0.3375(3) 0.4719(2) 0.0624(7) Uani 1 1 d . . . C6 C 0.5995(3) 0.7215(4) 0.3721(2) 0.0709(7) Uani 1 1 d . . . H6 H 0.5920 0.8324 0.3996 0.085 Uiso 1 1 calc R . . C7 C 0.5331(3) 0.6634(4) 0.2621(3) 0.0836(8) Uani 1 1 d . . . H7 H 0.4807 0.7348 0.2155 0.100 Uiso 1 1 calc R . . C8 C 0.5435(3) 0.4988(5) 0.2199(2) 0.0850(9) Uani 1 1 d . . . H8 H 0.4985 0.4598 0.1449 0.102 Uiso 1 1 calc R . . C9 C 0.6204(3) 0.3929(3) 0.2888(2) 0.0705(7) Uani 1 1 d . . . H9 H 0.6259 0.2821 0.2604 0.085 Uiso 1 1 calc R . . C10 C 0.7217(4) 0.8517(3) 0.5989(2) 0.0831(8) Uani 1 1 d . . . H10A H 0.7618 0.8720 0.6797 0.125 Uiso 1 1 calc R . . H10B H 0.6027 0.8678 0.5913 0.125 Uiso 1 1 calc R . . H10C H 0.7860 0.9283 0.5535 0.125 Uiso 1 1 calc R . . C11 C 1.0641(3) 0.2436(3) 0.8232(2) 0.0568(6) Uani 1 1 d U . . C12 C 1.0777(3) 0.0803(3) 0.7801(2) 0.0651(7) Uani 1 1 d . . . H12 H 1.0362 0.0423 0.7042 0.078 Uiso 1 1 calc R . . C13 C 1.1524(3) -0.0249(3) 0.8497(2) 0.0665(7) Uani 1 1 d . . . H13 H 1.1593 -0.1359 0.8222 0.080 Uiso 1 1 calc R . . C14 C 1.2169(3) 0.0341(3) 0.9602(2) 0.0588(6) Uani 1 1 d . . . C15 C 1.2061(3) 0.1975(3) 1.0032(2) 0.0662(7) Uani 1 1 d . . . H15 H 1.2505 0.2359 1.0784 0.079 Uiso 1 1 calc R . . C16 C 1.1300(3) 0.3026(3) 0.9346(2) 0.0650(7) Uani 1 1 d . . . H16 H 1.1224 0.4131 0.9627 0.078 Uiso 1 1 calc R . . N1 N 0.7442(2) 0.6796(2) 0.55631(17) 0.0594(5) Uani 1 1 d . . . N2 N 0.9202(2) 0.3046(2) 0.65071(18) 0.0612(6) Uani 1 1 d U . . N3 N 0.9855(2) 0.3547(2) 0.75549(17) 0.0631(5) Uani 1 1 d U . . H3 H 0.9804 0.4564 0.7835 0.076 Uiso 1 1 calc R . . N4 N 1.2980(3) -0.0773(4) 1.0342(2) 0.0783(7) Uani 1 1 d . . . O1 O 0.8851(2) 0.6436(2) 0.72844(15) 0.0758(5) Uani 1 1 d . . . O2 O 0.7830(3) 0.1904(2) 0.43668(15) 0.0888(6) Uani 1 1 d . . . O3 O 1.2941(3) -0.2261(3) 0.99960(19) 0.1069(7) Uani 1 1 d . . . O4 O 1.3684(3) -0.0180(3) 1.12808(19) 0.1081(8) Uani 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 0.0499(14) 0.0616(16) 0.0566(15) 0.0126(12) 0.0061(12) 0.0009(12) C2 0.0548(15) 0.0659(17) 0.0564(16) 0.0091(14) 0.0040(13) -0.0038(13) C3 0.0463(13) 0.0707(18) 0.0548(16) 0.0181(14) 0.0082(12) -0.0024(12) C4 0.0526(14) 0.0667(17) 0.0513(15) 0.0127(13) 0.0067(12) -0.0001(12) C5 0.0634(16) 0.0625(17) 0.0607(17) 0.0078(15) 0.0075(14) 0.0001(14) C6 0.0638(16) 0.0867(19) 0.0654(18) 0.0261(16) 0.0059(15) 0.0073(14) C7 0.0720(18) 0.100(2) 0.083(2) 0.0344(19) 0.0036(17) 0.0065(17) C8 0.0689(18) 0.118(3) 0.0651(18) 0.0193(19) -0.0032(15) -0.0097(18) C9 0.0692(17) 0.0810(18) 0.0591(16) 0.0097(14) 0.0010(14) -0.0034(14) C10 0.102(2) 0.0606(17) 0.084(2) 0.0067(15) 0.0001(17) 0.0025(15) C11 0.0497(14) 0.0634(16) 0.0587(16) 0.0139(13) 0.0056(12) 0.0048(12) C12 0.0617(16) 0.0726(18) 0.0595(16) 0.0083(14) -0.0046(13) 0.0015(13) C13 0.0662(16) 0.0603(16) 0.0713(18) 0.0036(14) 0.0021(14) 0.0024(13) C14 0.0533(14) 0.0652(17) 0.0597(16) 0.0127(14) 0.0037(13) 0.0086(13) C15 0.0605(15) 0.083(2) 0.0537(15) 0.0035(15) -0.0016(12) 0.0081(14) C16 0.0692(16) 0.0648(16) 0.0608(16) 0.0028(14) -0.0002(14) 0.0109(13) N1 0.0625(13) 0.0525(12) 0.0629(14) 0.0108(10) 0.0031(11) 0.0003(10) N2 0.0534(12) 0.0734(14) 0.0555(13) 0.0096(10) 0.0012(10) -0.0016(10) N3 0.0616(12) 0.0660(13) 0.0607(13) 0.0081(11) 0.0015(11) 0.0014(10) N4 0.0716(15) 0.0922(19) 0.0761(17) 0.0223(16) 0.0038(13) 0.0204(14) O1 0.0876(12) 0.0727(12) 0.0630(11) -0.0006(9) -0.0089(10) 0.0004(9) O2 0.1225(15) 0.0699(13) 0.0730(13) 0.0015(10) -0.0080(11) 0.0162(11) O3 0.1294(17) 0.0873(15) 0.1097(18) 0.0198(13) -0.0033(14) 0.0349(13) O4 0.1218(17) 0.1279(18) 0.0775(14) 0.0135(13) -0.0258(13) 0.0393(14) _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 N2 1.320(3) . ? C1 C2 1.467(3) . ? C1 C5 1.471(3) . ? C2 O1 1.242(2) . ? C2 N1 1.369(3) . ? C3 C6 1.387(3) . ? C3 C4 1.406(3) . ? C3 N1 1.407(3) . ? C4 C9 1.395(3) . ? C4 C5 1.447(3) . ? C5 O2 1.231(3) . ? C6 C7 1.366(3) . ? C6 H6 0.9300 . ? C7 C8 1.385(4) . ? C7 H7 0.9300 . ? C8 C9 1.375(4) . ? C8 H8 0.9300 . ? C9 H9 0.9300 . ? C10 N1 1.461(3) . ? C10 H10A 0.9600 . ? C10 H10B 0.9600 . ? C10 H10C 0.9600 . ? C11 C16 1.381(3) . ? C11 C12 1.382(3) . ? C11 N3 1.402(3) . ? C12 C13 1.368(3) . ? C12 H12 0.9300 . ? C13 C14 1.370(3) . ? C13 H13 0.9300 . ? C14 C15 1.378(3) . ? C14 N4 1.457(3) . ? C15 C16 1.365(3) . ? C15 H15 0.9300 . ? C16 H16 0.9300 . ? N2 N3 1.298(2) . ? N3 H3 0.8600 . ? N4 O4 1.222(3) . ? N4 O3 1.226(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 N2 C1 C2 124.3(2) . . ? N2 C1 C5 114.8(2) . . ? C2 C1 C5 120.9(2) . . ? O1 C2 N1 120.8(2) . . ? O1 C2 C1 120.7(2) . . ? N1 C2 C1 118.5(2) . . ? C6 C3 C4 119.5(2) . . ? C6 C3 N1 119.6(2) . . ? C4 C3 N1 120.8(2) . . ? C9 C4 C3 118.7(2) . . ? C9 C4 C5 120.1(2) . . ? C3 C4 C5 121.2(2) . . ? O2 C5 C4 121.9(2) . . ? O2 C5 C1 122.0(2) . . ? C4 C5 C1 116.1(2) . . ? C7 C6 C3 120.7(3) . . ? C7 C6 H6 119.6 . . ? C3 C6 H6 119.6 . . ? C6 C7 C8 120.3(3) . . ? C6 C7 H7 119.8 . . ? C8 C7 H7 119.8 . . ? C9 C8 C7 119.9(3) . . ? C9 C8 H8 120.0 . . ? C7 C8 H8 120.0 . . ? C8 C9 C4 120.7(3) . . ? C8 C9 H9 119.6 . . ? C4 C9 H9 119.6 . . ? N1 C10 H10A 109.5 . . ? N1 C10 H10B 109.5 . . ? H10A C10 H10B 109.5 . . ? N1 C10 H10C 109.5 . . ? H10A C10 H10C 109.5 . . ? H10B C10 H10C 109.5 . . ? C16 C11 C12 120.5(2) . . ? C16 C11 N3 118.1(2) . . ? C12 C11 N3 121.4(2) . . ? C13 C12 C11 119.6(2) . . ? C13 C12 H12 120.2 . . ? C11 C12 H12 120.2 . . ? C12 C13 C14 119.6(2) . . ? C12 C13 H13 120.2 . . ? C14 C13 H13 120.2 . . ? C13 C14 C15 121.1(2) . . ? C13 C14 N4 119.7(3) . . ? C15 C14 N4 119.2(3) . . ? C16 C15 C14 119.6(2) . . ? C16 C15 H15 120.2 . . ? C14 C15 H15 120.2 . . ? C15 C16 C11 119.6(2) . . ? C15 C16 H16 120.2 . . ? C11 C16 H16 120.2 . . ? C2 N1 C3 122.4(2) . . ? C2 N1 C10 118.4(2) . . ? C3 N1 C10 119.2(2) . . ? N3 N2 C1 119.8(2) . . ? N2 N3 C11 120.3(2) . . ? N2 N3 H3 119.8 . . ? C11 N3 H3 119.8 . . ? O4 N4 O3 122.7(2) . . ? O4 N4 C14 118.4(3) . . ? O3 N4 C14 118.9(3) . . ? _diffrn_measured_fraction_theta_max 0.986 _diffrn_reflns_theta_full 24.98 _diffrn_measured_fraction_theta_full 0.986 _refine_diff_density_max 0.169 _refine_diff_density_min -0.137 _refine_diff_density_rms 0.032