data_11 _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C15 H12 N4 O6' _chemical_formula_weight 344.29 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 monoclinic _symmetry_space_group_name_H-M P21/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 4.6008(7) _cell_length_b 14.451(2) _cell_length_c 23.296(3) _cell_angle_alpha 90.00 _cell_angle_beta 93.620(2) _cell_angle_gamma 90.00 _cell_volume 1545.8(4) _cell_formula_units_Z 4 _cell_measurement_temperature 298(2) _cell_measurement_reflns_used 2907 _cell_measurement_theta_min 2.8 _cell_measurement_theta_max 25.0 _exptl_crystal_description block _exptl_crystal_colour yellow _exptl_crystal_size_max 0.17 _exptl_crystal_size_mid 0.13 _exptl_crystal_size_min 0.10 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.479 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 712 _exptl_absorpt_coefficient_mu 0.117 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.9803 _exptl_absorpt_correction_T_max 0.9884 _exptl_absorpt_process_details SADABS _exptl_special_details ; ? ; _diffrn_ambient_temperature 298(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 ? _diffrn_measurement_method ? _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 12373 _diffrn_reflns_av_R_equivalents 0.0268 _diffrn_reflns_av_sigmaI/netI 0.0294 _diffrn_reflns_limit_h_min -5 _diffrn_reflns_limit_h_max 5 _diffrn_reflns_limit_k_min -16 _diffrn_reflns_limit_k_max 18 _diffrn_reflns_limit_l_min -29 _diffrn_reflns_limit_l_max 29 _diffrn_reflns_theta_min 2.25 _diffrn_reflns_theta_max 27.00 _reflns_number_total 3343 _reflns_number_gt 2193 _reflns_threshold_expression >2sigma(I) _computing_data_collection ? _computing_cell_refinement ? _computing_data_reduction ? _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _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^)+(0.0463P)^2^+0.3387P] 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 3343 _refine_ls_number_parameters 229 _refine_ls_number_restraints 1 _refine_ls_R_factor_all 0.0762 _refine_ls_R_factor_gt 0.0441 _refine_ls_wR_factor_ref 0.1138 _refine_ls_wR_factor_gt 0.0985 _refine_ls_goodness_of_fit_ref 1.020 _refine_ls_restrained_S_all 1.020 _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 N1 N 1.4203(3) 0.94728(12) 0.59365(8) 0.0553(4) Uani 1 1 d . . . N2 N 0.4690(3) 0.65702(10) 0.48708(5) 0.0379(3) Uani 1 1 d . . . N3 N 0.2645(3) 0.58784(10) 0.48055(6) 0.0378(3) Uani 1 1 d D . . N4 N 0.3800(5) 0.31402(16) 0.19938(10) 0.0816(6) Uani 1 1 d . . . O1 O 1.4274(4) 1.01410(12) 0.56207(8) 0.0952(6) Uani 1 1 d . . . O2 O 1.5758(3) 0.93911(12) 0.63709(7) 0.0819(5) Uani 1 1 d . . . O3 O -0.0733(3) 0.51588(9) 0.42316(5) 0.0453(3) Uani 1 1 d . . . O4 O 0.0437(3) 0.61559(9) 0.32851(5) 0.0500(3) Uani 1 1 d . . . O5 O 0.5481(6) 0.25791(17) 0.22243(11) 0.1326(9) Uani 1 1 d . . . O6 O 0.2775(5) 0.30844(14) 0.15016(8) 0.1040(7) Uani 1 1 d . . . C1 C 1.2118(4) 0.87272(12) 0.57836(8) 0.0425(4) Uani 1 1 d . . . C2 C 1.0780(4) 0.87140(13) 0.52364(8) 0.0459(4) Uani 1 1 d . . . H2 H 1.1223 0.9159 0.4967 0.055 Uiso 1 1 calc R . . C3 C 0.8781(4) 0.80313(12) 0.50960(7) 0.0429(4) Uani 1 1 d . . . H3 H 0.7854 0.8014 0.4730 0.051 Uiso 1 1 calc R . . C4 C 0.8138(3) 0.73627(12) 0.55018(7) 0.0371(4) Uani 1 1 d . . . C5 C 0.9564(4) 0.73895(13) 0.60439(7) 0.0460(5) Uani 1 1 d . . . H5 H 0.9164 0.6940 0.6313 0.055 Uiso 1 1 calc R . . C6 C 1.1575(4) 0.80765(14) 0.61896(8) 0.0491(5) Uani 1 1 d . . . H6 H 1.2529 0.8095 0.6553 0.059 Uiso 1 1 calc R . . C7 C 0.5967(3) 0.66437(12) 0.53712(7) 0.0385(4) Uani 1 1 d . . . H7 H 0.5506 0.6231 0.5658 0.046 Uiso 1 1 calc R . . C8 C 0.1153(4) 0.57582(11) 0.42926(7) 0.0368(4) Uani 1 1 d . . . C9 C 0.1939(4) 0.63988(13) 0.38129(7) 0.0482(5) Uani 1 1 d . . . H9A H 0.1454 0.7030 0.3911 0.058 Uiso 1 1 calc R . . H9B H 0.4021 0.6369 0.3771 0.058 Uiso 1 1 calc R . . C10 C 0.1442(4) 0.54189(13) 0.29936(7) 0.0415(4) Uani 1 1 d . . . C11 C 0.3694(4) 0.48459(14) 0.31917(7) 0.0487(5) Uani 1 1 d . . . H11 H 0.4707 0.4965 0.3542 0.058 Uiso 1 1 calc R . . C12 C 0.4426(4) 0.40935(15) 0.28634(8) 0.0565(5) Uani 1 1 d . . . H12 H 0.5910 0.3696 0.2996 0.068 Uiso 1 1 calc R . . C13 C 0.2960(4) 0.39355(15) 0.23429(8) 0.0553(5) Uani 1 1 d . . . C14 C 0.0792(4) 0.45153(15) 0.21306(8) 0.0563(5) Uani 1 1 d . . . H14 H -0.0144 0.4408 0.1771 0.068 Uiso 1 1 calc R . . C15 C 0.0021(4) 0.52595(14) 0.24573(8) 0.0522(5) Uani 1 1 d . . . H15 H -0.1452 0.5657 0.2319 0.063 Uiso 1 1 calc R . . H3A H 0.211(5) 0.5534(13) 0.5104(7) 0.080 Uiso 1 1 d 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 N1 0.0484(10) 0.0532(11) 0.0634(10) -0.0166(9) -0.0028(8) -0.0066(8) N2 0.0354(7) 0.0384(8) 0.0397(8) -0.0034(6) 0.0002(6) -0.0033(6) N3 0.0382(8) 0.0403(8) 0.0345(7) 0.0002(6) -0.0007(6) -0.0085(6) N4 0.0860(15) 0.0790(16) 0.0814(15) -0.0215(13) 0.0185(12) -0.0055(12) O1 0.1137(15) 0.0640(11) 0.1040(13) 0.0068(10) -0.0232(11) -0.0402(11) O2 0.0690(10) 0.0879(12) 0.0846(11) -0.0144(9) -0.0280(9) -0.0217(9) O3 0.0465(7) 0.0512(8) 0.0373(6) -0.0001(5) -0.0044(5) -0.0138(6) O4 0.0610(8) 0.0510(8) 0.0367(6) 0.0034(6) -0.0081(6) -0.0005(6) O5 0.143(2) 0.1172(18) 0.1367(19) -0.0418(15) -0.0011(15) 0.0558(17) O6 0.1348(17) 0.1071(15) 0.0718(11) -0.0355(11) 0.0210(11) -0.0184(13) C1 0.0326(9) 0.0407(10) 0.0538(10) -0.0115(8) -0.0014(8) -0.0014(8) C2 0.0479(11) 0.0414(10) 0.0479(10) 0.0005(8) 0.0005(8) -0.0034(8) C3 0.0442(10) 0.0452(10) 0.0383(9) -0.0017(8) -0.0045(8) -0.0032(8) C4 0.0311(9) 0.0407(10) 0.0391(9) -0.0054(7) -0.0001(7) 0.0011(7) C5 0.0442(10) 0.0511(11) 0.0420(9) 0.0024(8) -0.0024(8) -0.0043(9) C6 0.0439(10) 0.0597(12) 0.0423(10) -0.0076(9) -0.0072(8) -0.0021(9) C7 0.0377(9) 0.0398(10) 0.0380(9) 0.0013(7) 0.0020(7) 0.0002(8) C8 0.0371(9) 0.0380(10) 0.0351(8) -0.0037(7) -0.0005(7) -0.0005(8) C9 0.0633(12) 0.0438(11) 0.0365(9) 0.0022(8) -0.0053(8) -0.0087(9) C10 0.0433(10) 0.0493(11) 0.0317(8) 0.0061(8) 0.0001(7) -0.0085(8) C11 0.0459(11) 0.0633(13) 0.0360(9) 0.0058(9) -0.0035(8) -0.0047(9) C12 0.0491(11) 0.0650(14) 0.0559(12) 0.0056(10) 0.0064(9) 0.0061(10) C13 0.0554(12) 0.0603(13) 0.0513(11) -0.0062(10) 0.0133(9) -0.0087(10) C14 0.0556(12) 0.0739(15) 0.0387(10) -0.0068(10) -0.0016(9) -0.0119(11) C15 0.0513(11) 0.0662(13) 0.0380(9) 0.0054(9) -0.0065(8) -0.0025(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 N1 O2 1.208(2) . ? N1 O1 1.216(2) . ? N1 C1 1.471(2) . ? N2 C7 1.2764(19) . ? N2 N3 1.3747(18) . ? N3 C8 1.3511(19) . ? N3 H3A 0.903(10) . ? N4 O6 1.215(2) . ? N4 O5 1.221(3) . ? N4 C13 1.474(3) . ? O3 C8 1.2280(19) . ? O4 C10 1.360(2) . ? O4 C9 1.4163(19) . ? C1 C6 1.368(3) . ? C1 C2 1.380(2) . ? C2 C3 1.374(2) . ? C2 H2 0.9300 . ? C3 C4 1.396(2) . ? C3 H3 0.9300 . ? C4 C5 1.386(2) . ? C4 C7 1.460(2) . ? C5 C6 1.385(2) . ? C5 H5 0.9300 . ? C6 H6 0.9300 . ? C7 H7 0.9300 . ? C8 C9 1.512(2) . ? C9 H9A 0.9700 . ? C9 H9B 0.9700 . ? C10 C11 1.383(3) . ? C10 C15 1.392(2) . ? C11 C12 1.383(3) . ? C11 H11 0.9300 . ? C12 C13 1.369(3) . ? C12 H12 0.9300 . ? C13 C14 1.371(3) . ? C14 C15 1.377(3) . ? C14 H14 0.9300 . ? C15 H15 0.9300 . ? 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 O2 N1 O1 123.21(18) . . ? O2 N1 C1 118.29(18) . . ? O1 N1 C1 118.50(17) . . ? C7 N2 N3 115.71(14) . . ? C8 N3 N2 119.81(14) . . ? C8 N3 H3A 117.6(14) . . ? N2 N3 H3A 122.2(14) . . ? O6 N4 O5 124.6(2) . . ? O6 N4 C13 118.2(2) . . ? O5 N4 C13 117.1(2) . . ? C10 O4 C9 117.71(14) . . ? C6 C1 C2 122.59(16) . . ? C6 C1 N1 118.74(16) . . ? C2 C1 N1 118.67(17) . . ? C3 C2 C1 118.85(17) . . ? C3 C2 H2 120.6 . . ? C1 C2 H2 120.6 . . ? C2 C3 C4 120.19(15) . . ? C2 C3 H3 119.9 . . ? C4 C3 H3 119.9 . . ? C5 C4 C3 119.28(16) . . ? C5 C4 C7 119.20(16) . . ? C3 C4 C7 121.51(14) . . ? C6 C5 C4 120.92(17) . . ? C6 C5 H5 119.5 . . ? C4 C5 H5 119.5 . . ? C1 C6 C5 118.15(16) . . ? C1 C6 H6 120.9 . . ? C5 C6 H6 120.9 . . ? N2 C7 C4 121.27(16) . . ? N2 C7 H7 119.4 . . ? C4 C7 H7 119.4 . . ? O3 C8 N3 120.57(15) . . ? O3 C8 C9 123.13(14) . . ? N3 C8 C9 116.30(14) . . ? O4 C9 C8 111.32(14) . . ? O4 C9 H9A 109.4 . . ? C8 C9 H9A 109.4 . . ? O4 C9 H9B 109.4 . . ? C8 C9 H9B 109.4 . . ? H9A C9 H9B 108.0 . . ? O4 C10 C11 125.01(15) . . ? O4 C10 C15 114.99(16) . . ? C11 C10 C15 120.00(18) . . ? C10 C11 C12 119.31(17) . . ? C10 C11 H11 120.3 . . ? C12 C11 H11 120.3 . . ? C13 C12 C11 119.83(19) . . ? C13 C12 H12 120.1 . . ? C11 C12 H12 120.1 . . ? C12 C13 C14 121.6(2) . . ? C12 C13 N4 119.2(2) . . ? C14 C13 N4 119.20(19) . . ? C13 C14 C15 119.02(18) . . ? C13 C14 H14 120.5 . . ? C15 C14 H14 120.5 . . ? C14 C15 C10 120.16(19) . . ? C14 C15 H15 119.9 . . ? C10 C15 H15 119.9 . . ? loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA _geom_hbond_site_symmetry_A N3 H3A O3 0.903(10) 1.980(10) 2.8811(18) 176(2) 3_566 _diffrn_measured_fraction_theta_max 0.993 _diffrn_reflns_theta_full 27.00 _diffrn_measured_fraction_theta_full 0.993 _refine_diff_density_max 0.213 _refine_diff_density_min -0.140 _refine_diff_density_rms 0.032