# Electronic Supplementary Material (ESI) for New Journal of Chemistry # This journal is © The Royal Society of Chemistry and The Centre National de la Recherche Scientifique 2013 ####################################################################### # # Cambridge Crystallographic Data Centre # CCDC # ####################################################################### # # This CIF contains data from an original supplementary publication # deposited with the CCDC, and may include chemical, crystal, # experimental, refinement, atomic coordinates, # anisotropic displacement parameters and molecular geometry data, # as required by the journal to which it was submitted. # # This CIF is provided on the understanding that it is used for bona # fide research purposes only. It may contain copyright material # of the CCDC or of third parties, and may not be copied or further # disseminated in any form, whether machine-readable or not, # except for the purpose of generating routine backup copies # on your local computer system. # # For further information on the CCDC, data deposition and # data retrieval see: # www.ccdc.cam.ac.uk # # Bona fide researchers may freely download Mercury and enCIFer # from this site to visualise CIF-encoded structures and # to carry out CIF format checking respectively. # data_x1 #TrackingRef 'X24piccl CCDC.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C9 H3 N7 O10' _chemical_formula_weight 369.18 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/N loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, y+1/2, -z+1/2' '-x, -y, -z' 'x-1/2, -y-1/2, z-1/2' _cell_length_a 8.7000(17) _cell_length_b 11.397(2) _cell_length_c 14.164(3) _cell_angle_alpha 90.00 _cell_angle_beta 92.50(3) _cell_angle_gamma 90.00 _cell_volume 1403.1(5) _cell_formula_units_Z 4 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 25 _cell_measurement_theta_min 10 _cell_measurement_theta_max 13 _exptl_crystal_description ? _exptl_crystal_colour ? _exptl_crystal_size_max 0.30 _exptl_crystal_size_mid 0.20 _exptl_crystal_size_min 0.10 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.748 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 744 _exptl_absorpt_coefficient_mu 0.162 _exptl_absorpt_correction_type psi-scan _exptl_absorpt_correction_T_min 0.9531 _exptl_absorpt_correction_T_max 0.9840 _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 293(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 'Nonius cad4' _diffrn_measurement_method \w/2\q _diffrn_detector_area_resol_mean ? _diffrn_standards_number 3 _diffrn_standards_interval_count 200 _diffrn_standards_interval_time 2h _diffrn_standards_decay_% 1 _diffrn_reflns_number 2690 _diffrn_reflns_av_R_equivalents 0.0274 _diffrn_reflns_av_sigmaI/netI 0.0360 _diffrn_reflns_limit_h_min 0 _diffrn_reflns_limit_h_max 10 _diffrn_reflns_limit_k_min 0 _diffrn_reflns_limit_k_max 13 _diffrn_reflns_limit_l_min -17 _diffrn_reflns_limit_l_max 17 _diffrn_reflns_theta_min 2.29 _diffrn_reflns_theta_max 25.31 _reflns_number_total 2518 _reflns_number_gt 1778 _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^)+(0.1000P)^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 constr _refine_ls_extinction_method SHELXL _refine_ls_extinction_coef 0.037(4) _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_number_reflns 2518 _refine_ls_number_parameters 236 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0766 _refine_ls_R_factor_gt 0.0508 _refine_ls_wR_factor_ref 0.1583 _refine_ls_wR_factor_gt 0.1398 _refine_ls_goodness_of_fit_ref 1.004 _refine_ls_restrained_S_all 1.004 _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 0.4150(2) 0.4897(2) 0.38527(16) 0.0491(6) Uani 1 1 d . . . C1 C 0.3597(3) 0.3991(3) 0.33802(19) 0.0468(7) Uani 1 1 d . . . O1 O 0.5846(3) 0.3411(3) 0.2772(2) 0.1044(11) Uani 1 1 d . . . N2 N 0.2042(2) 0.38556(19) 0.34321(14) 0.0393(5) Uani 1 1 d . . . C2 C 0.1581(3) 0.4754(2) 0.39930(17) 0.0388(6) Uani 1 1 d . . . H2A H 0.0585 0.4915 0.4169 0.047 Uiso 1 1 calc R . . O2 O 0.3837(3) 0.2300(2) 0.25021(18) 0.0768(8) Uani 1 1 d . . . C3 C 0.2884(3) 0.5365(2) 0.42421(17) 0.0403(6) Uani 1 1 d . . . O3 O 0.1793(3) 0.6597(2) 0.52922(18) 0.0748(7) Uani 1 1 d . . . N3 N 0.4499(3) 0.3171(3) 0.2839(2) 0.0625(7) Uani 1 1 d . . . C4 C 0.0987(3) 0.3015(2) 0.29850(17) 0.0376(6) Uani 1 1 d . . . N4 N 0.2952(3) 0.6393(2) 0.48544(16) 0.0509(6) Uani 1 1 d . . . O4 O 0.4123(3) 0.6984(2) 0.49139(16) 0.0710(7) Uani 1 1 d . . . N5 N 0.1162(3) 0.1729(2) 0.44194(18) 0.0558(7) Uani 1 1 d . . . C5 C 0.0445(3) 0.2049(2) 0.34815(17) 0.0408(6) Uani 1 1 d . . . O5 O 0.0361(3) 0.1225(3) 0.49738(18) 0.0901(9) Uani 1 1 d . . . N6 N -0.2730(3) 0.0971(2) 0.18644(19) 0.0550(7) Uani 1 1 d . . . O6 O 0.2522(3) 0.1969(2) 0.45645(16) 0.0714(7) Uani 1 1 d . . . C6 C -0.0769(3) 0.1368(2) 0.3134(2) 0.0457(7) Uani 1 1 d . . . H6A H -0.1130 0.0734 0.3473 0.055 Uiso 1 1 calc R . . C7 C -0.1425(3) 0.1673(2) 0.22581(19) 0.0435(7) Uani 1 1 d . . . N7 N 0.0844(3) 0.4276(2) 0.15214(16) 0.0563(7) Uani 1 1 d . . . O7 O -0.3270(3) 0.0220(3) 0.2357(2) 0.0867(9) Uani 1 1 d . . . C8 C -0.0925(3) 0.2613(2) 0.17245(18) 0.0433(7) Uani 1 1 d . . . H8A H -0.1388 0.2791 0.1138 0.052 Uiso 1 1 calc R . . O8 O -0.3219(3) 0.1198(2) 0.10627(17) 0.0779(8) Uani 1 1 d . . . C9 C 0.0294(3) 0.3274(2) 0.21040(18) 0.0420(7) Uani 1 1 d . . . O9 O -0.0083(3) 0.4752(3) 0.09897(18) 0.0922(9) Uani 1 1 d . . . O10 O 0.2199(3) 0.4549(3) 0.16088(18) 0.0856(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 N1 0.0386(12) 0.0604(15) 0.0484(13) -0.0098(11) 0.0033(10) -0.0095(11) C1 0.0335(14) 0.0590(18) 0.0480(15) -0.0086(14) 0.0054(11) -0.0025(13) O1 0.0417(14) 0.137(3) 0.137(3) -0.060(2) 0.0275(15) -0.0087(15) N2 0.0338(11) 0.0435(12) 0.0403(11) -0.0054(10) -0.0014(9) -0.0024(9) C2 0.0365(13) 0.0439(15) 0.0356(13) -0.0031(12) -0.0027(10) 0.0012(11) O2 0.0577(14) 0.0792(17) 0.0939(18) -0.0393(15) 0.0079(13) 0.0007(13) C3 0.0431(14) 0.0406(14) 0.0370(13) -0.0001(11) -0.0008(11) -0.0052(12) O3 0.0649(15) 0.0758(16) 0.0848(16) -0.0340(13) 0.0162(13) -0.0071(12) N3 0.0431(14) 0.0767(19) 0.0681(17) -0.0230(15) 0.0070(12) 0.0007(14) C4 0.0319(13) 0.0459(15) 0.0348(13) -0.0052(12) 0.0002(10) -0.0018(11) N4 0.0545(15) 0.0496(14) 0.0486(14) -0.0061(11) 0.0017(12) -0.0127(13) O4 0.0762(15) 0.0674(15) 0.0696(14) -0.0150(12) 0.0068(12) -0.0340(13) N5 0.0740(18) 0.0461(15) 0.0461(14) 0.0027(12) -0.0110(13) 0.0007(13) C5 0.0433(14) 0.0429(15) 0.0357(13) -0.0046(11) -0.0051(11) 0.0037(12) O5 0.117(2) 0.091(2) 0.0616(14) 0.0315(14) -0.0063(15) -0.0217(17) N6 0.0425(13) 0.0613(17) 0.0608(16) -0.0134(13) -0.0012(12) -0.0087(12) O6 0.0719(16) 0.0754(16) 0.0640(14) 0.0006(12) -0.0304(12) -0.0004(13) C6 0.0489(16) 0.0411(15) 0.0473(15) -0.0033(12) 0.0042(12) -0.0048(13) C7 0.0331(13) 0.0500(16) 0.0473(15) -0.0136(13) 0.0011(11) -0.0025(12) N7 0.0672(17) 0.0638(17) 0.0377(13) 0.0031(12) -0.0010(12) -0.0112(14) O7 0.0714(16) 0.0859(18) 0.102(2) 0.0134(15) -0.0117(14) -0.0385(15) C8 0.0407(14) 0.0533(17) 0.0354(14) -0.0090(12) -0.0028(11) 0.0015(13) O8 0.0645(15) 0.107(2) 0.0606(14) -0.0153(14) -0.0148(12) -0.0262(14) C9 0.0424(14) 0.0453(15) 0.0386(14) -0.0048(12) 0.0030(11) -0.0021(12) O9 0.102(2) 0.110(2) 0.0627(14) 0.0413(15) -0.0205(15) -0.0175(17) O10 0.0739(17) 0.102(2) 0.0806(17) 0.0272(15) -0.0001(13) -0.0346(15) _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 C1 1.311(4) . ? N1 C3 1.362(3) . ? C1 N2 1.367(3) . ? C1 N3 1.459(4) . ? O1 N3 1.211(3) . ? N2 C2 1.367(3) . ? N2 C4 1.453(3) . ? C2 C3 1.364(4) . ? C2 H2A 0.9300 . ? O2 N3 1.233(3) . ? C3 N4 1.457(3) . ? O3 N4 1.228(3) . ? C4 C9 1.393(4) . ? C4 C5 1.399(4) . ? N4 O4 1.221(3) . ? N5 O5 1.217(4) . ? N5 O6 1.223(3) . ? N5 C5 1.488(3) . ? C5 C6 1.384(4) . ? N6 O7 1.212(3) . ? N6 O8 1.223(3) . ? N6 C7 1.478(3) . ? C6 C7 1.386(4) . ? C6 H6A 0.9300 . ? C7 C8 1.391(4) . ? N7 O9 1.207(3) . ? N7 O10 1.220(3) . ? N7 C9 1.500(4) . ? C8 C9 1.390(4) . ? C8 H8A 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 C1 N1 C3 103.3(2) . . ? N1 C1 N2 113.8(2) . . ? N1 C1 N3 125.4(2) . . ? N2 C1 N3 120.8(2) . . ? C2 N2 C1 105.3(2) . . ? C2 N2 C4 123.5(2) . . ? C1 N2 C4 131.2(2) . . ? C3 C2 N2 105.7(2) . . ? C3 C2 H2A 127.1 . . ? N2 C2 H2A 127.1 . . ? N1 C3 C2 111.9(2) . . ? N1 C3 N4 122.9(2) . . ? C2 C3 N4 125.2(2) . . ? O1 N3 O2 126.1(3) . . ? O1 N3 C1 116.2(3) . . ? O2 N3 C1 117.8(2) . . ? C9 C4 C5 118.3(2) . . ? C9 C4 N2 119.4(2) . . ? C5 C4 N2 121.3(2) . . ? O4 N4 O3 124.2(3) . . ? O4 N4 C3 119.7(2) . . ? O3 N4 C3 116.1(2) . . ? O5 N5 O6 125.1(3) . . ? O5 N5 C5 117.5(3) . . ? O6 N5 C5 117.4(3) . . ? C6 C5 C4 122.1(2) . . ? C6 C5 N5 117.7(3) . . ? C4 C5 N5 120.3(2) . . ? O7 N6 O8 123.8(3) . . ? O7 N6 C7 118.4(3) . . ? O8 N6 C7 117.8(3) . . ? C5 C6 C7 117.1(3) . . ? C5 C6 H6A 121.4 . . ? C7 C6 H6A 121.4 . . ? C6 C7 C8 123.5(2) . . ? C6 C7 N6 118.8(3) . . ? C8 C7 N6 117.7(2) . . ? O9 N7 O10 124.4(3) . . ? O9 N7 C9 117.7(3) . . ? O10 N7 C9 117.9(3) . . ? C9 C8 C7 117.3(2) . . ? C9 C8 H8A 121.4 . . ? C7 C8 H8A 121.4 . . ? C8 C9 C4 121.7(2) . . ? C8 C9 N7 117.1(2) . . ? C4 C9 N7 121.2(2) . . ? 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 C3 N1 C1 N2 0.8(3) . . . . ? C3 N1 C1 N3 -179.1(3) . . . . ? N1 C1 N2 C2 -0.5(3) . . . . ? N3 C1 N2 C2 179.5(2) . . . . ? N1 C1 N2 C4 176.7(2) . . . . ? N3 C1 N2 C4 -3.3(4) . . . . ? C1 N2 C2 C3 -0.1(3) . . . . ? C4 N2 C2 C3 -177.6(2) . . . . ? C1 N1 C3 C2 -0.9(3) . . . . ? C1 N1 C3 N4 178.7(2) . . . . ? N2 C2 C3 N1 0.7(3) . . . . ? N2 C2 C3 N4 -178.9(2) . . . . ? N1 C1 N3 O1 -5.6(5) . . . . ? N2 C1 N3 O1 174.5(3) . . . . ? N1 C1 N3 O2 173.6(3) . . . . ? N2 C1 N3 O2 -6.3(4) . . . . ? C2 N2 C4 C9 87.2(3) . . . . ? C1 N2 C4 C9 -89.5(3) . . . . ? C2 N2 C4 C5 -81.7(3) . . . . ? C1 N2 C4 C5 101.6(3) . . . . ? N1 C3 N4 O4 12.0(4) . . . . ? C2 C3 N4 O4 -168.5(3) . . . . ? N1 C3 N4 O3 -167.3(3) . . . . ? C2 C3 N4 O3 12.3(4) . . . . ? C9 C4 C5 C6 -1.5(4) . . . . ? N2 C4 C5 C6 167.5(2) . . . . ? C9 C4 C5 N5 179.2(2) . . . . ? N2 C4 C5 N5 -11.8(4) . . . . ? O5 N5 C5 C6 -27.1(4) . . . . ? O6 N5 C5 C6 151.2(3) . . . . ? O5 N5 C5 C4 152.3(3) . . . . ? O6 N5 C5 C4 -29.4(4) . . . . ? C4 C5 C6 C7 0.9(4) . . . . ? N5 C5 C6 C7 -179.8(2) . . . . ? C5 C6 C7 C8 0.0(4) . . . . ? C5 C6 C7 N6 -179.7(2) . . . . ? O7 N6 C7 C6 6.5(4) . . . . ? O8 N6 C7 C6 -174.7(3) . . . . ? O7 N6 C7 C8 -173.2(3) . . . . ? O8 N6 C7 C8 5.6(4) . . . . ? C6 C7 C8 C9 -0.3(4) . . . . ? N6 C7 C8 C9 179.5(2) . . . . ? C7 C8 C9 C4 -0.4(4) . . . . ? C7 C8 C9 N7 179.2(2) . . . . ? C5 C4 C9 C8 1.3(4) . . . . ? N2 C4 C9 C8 -168.0(2) . . . . ? C5 C4 C9 N7 -178.4(2) . . . . ? N2 C4 C9 N7 12.4(4) . . . . ? O9 N7 C9 C8 29.2(4) . . . . ? O10 N7 C9 C8 -150.1(3) . . . . ? O9 N7 C9 C4 -151.2(3) . . . . ? O10 N7 C9 C4 29.6(4) . . . . ? _diffrn_measured_fraction_theta_max 0.984 _diffrn_reflns_theta_full 25.31 _diffrn_measured_fraction_theta_full 0.984 _refine_diff_density_max 0.197 _refine_diff_density_min -0.203 _refine_diff_density_rms 0.056 _database_code_depnum_ccdc_archive 'CCDC 884547' ####################################################################### # # Cambridge Crystallographic Data Centre # CCDC # ####################################################################### # # This CIF contains data from an original supplementary publication # deposited with the CCDC, and may include chemical, crystal, # experimental, refinement, atomic coordinates, # anisotropic displacement parameters and molecular geometry data, # as required by the journal to which it was submitted. # # This CIF is provided on the understanding that it is used for bona # fide research purposes only. It may contain copyright material # of the CCDC or of third parties, and may not be copied or further # disseminated in any form, whether machine-readable or not, # except for the purpose of generating routine backup copies # on your local computer system. # # For further information on the CCDC, data deposition and # data retrieval see: # www.ccdc.cam.ac.uk # # Bona fide researchers may freely download Mercury and enCIFer # from this site to visualise CIF-encoded structures and # to carry out CIF format checking respectively. # data_x #TrackingRef 'X24eranCCDC.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C9 H5 N9 O10' _chemical_formula_weight 399.22 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 Monoclinic _symmetry_space_group_name_H-M P21/N loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, y+1/2, -z+1/2' '-x, -y, -z' 'x-1/2, -y-1/2, z-1/2' _cell_length_a 9.0830(18) _cell_length_b 11.395(2) _cell_length_c 14.089(3) _cell_angle_alpha 90.00 _cell_angle_beta 99.23(3) _cell_angle_gamma 90.00 _cell_volume 1439.3(5) _cell_formula_units_Z 4 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 25 _cell_measurement_theta_min 10 _cell_measurement_theta_max 13 _exptl_crystal_description ? _exptl_crystal_colour ? _exptl_crystal_size_max 0.30 _exptl_crystal_size_mid 0.20 _exptl_crystal_size_min 0.10 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.842 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 808 _exptl_absorpt_coefficient_mu 0.169 _exptl_absorpt_correction_type psi-scan _exptl_absorpt_correction_T_min 0.9511 _exptl_absorpt_correction_T_max 0.9833 _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 293(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 'Nonius CAD4' _diffrn_measurement_method \w/2\q _diffrn_detector_area_resol_mean ? _diffrn_standards_number 3 _diffrn_standards_interval_count 200 _diffrn_standards_interval_time 2h _diffrn_standards_decay_% 1 _diffrn_reflns_number 2814 _diffrn_reflns_av_R_equivalents 0.0281 _diffrn_reflns_av_sigmaI/netI 0.0545 _diffrn_reflns_limit_h_min 0 _diffrn_reflns_limit_h_max 10 _diffrn_reflns_limit_k_min 0 _diffrn_reflns_limit_k_max 13 _diffrn_reflns_limit_l_min -16 _diffrn_reflns_limit_l_max 16 _diffrn_reflns_theta_min 2.31 _diffrn_reflns_theta_max 25.35 _reflns_number_total 2639 _reflns_number_gt 1747 _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^)+(0.0550P)^2^+0.0000P] 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 2639 _refine_ls_number_parameters 253 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0871 _refine_ls_R_factor_gt 0.0505 _refine_ls_wR_factor_ref 0.1217 _refine_ls_wR_factor_gt 0.1081 _refine_ls_goodness_of_fit_ref 1.001 _refine_ls_restrained_S_all 1.001 _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 0.0882(3) 0.32215(19) 0.57882(16) 0.0366(6) Uani 1 1 d . . . C1 C 0.0343(3) 0.2924(2) 0.66686(17) 0.0288(6) Uani 1 1 d . . . O1 O 0.2144(3) 0.29183(19) 0.56980(16) 0.0616(7) Uani 1 1 d . . . O2 O 0.0106(3) 0.37623(19) 0.51617(14) 0.0582(6) Uani 1 1 d . . . C2 C -0.0798(3) 0.3626(2) 0.69853(19) 0.0361(6) Uani 1 1 d . . . N2 N -0.1299(3) 0.4574(2) 0.64997(19) 0.0613(8) Uani 1 1 d . . . H2A H -0.1955 0.5011 0.6704 0.074 Uiso 1 1 calc R . . H2B H -0.0970 0.4755 0.5979 0.074 Uiso 1 1 calc R . . N3 N -0.2378(3) 0.3990(2) 0.82302(19) 0.0444(6) Uani 1 1 d . . . O3 O -0.2955(3) 0.4823(2) 0.77693(19) 0.0798(8) Uani 1 1 d . . . C3 C -0.1296(3) 0.3275(2) 0.78528(18) 0.0339(6) Uani 1 1 d . . . N4 N -0.1332(3) 0.1836(2) 0.91097(16) 0.0462(7) Uani 1 1 d . . . H4A H -0.2049 0.2205 0.9309 0.055 Uiso 1 1 calc R . . H4B H -0.0980 0.1205 0.9396 0.055 Uiso 1 1 calc R . . C4 C -0.0770(3) 0.2237(2) 0.83624(18) 0.0327(6) Uani 1 1 d . . . O4 O -0.2714(3) 0.3775(2) 0.90207(16) 0.0653(7) Uani 1 1 d . . . C5 C 0.0426(3) 0.1628(2) 0.80279(18) 0.0331(6) Uani 1 1 d . . . N5 N 0.1172(3) 0.0666(2) 0.85878(17) 0.0450(6) Uani 1 1 d . . . O5 O 0.0443(3) 0.0035(2) 0.90501(18) 0.0756(8) Uani 1 1 d . . . N6 N 0.1909(2) 0.11765(18) 0.67963(15) 0.0311(5) Uani 1 1 d . . . C6 C 0.0927(3) 0.1965(2) 0.71944(18) 0.0287(6) Uani 1 1 d . . . O6 O 0.2495(3) 0.0517(2) 0.85854(17) 0.0660(7) Uani 1 1 d . . . N7 N 0.3921(3) 0.0369(2) 0.63335(17) 0.0413(6) Uani 1 1 d . . . C7 C 0.1398(3) 0.0263(2) 0.62099(18) 0.0328(6) Uani 1 1 d . . . H7B H 0.0418 0.0012 0.6034 0.039 Uiso 1 1 calc R . . O7 O 0.5668(3) 0.2020(2) 0.7361(2) 0.0831(9) Uani 1 1 d . . . C8 C 0.2650(3) -0.0196(2) 0.59420(19) 0.0354(6) Uani 1 1 d . . . O8 O 0.3726(2) 0.2803(2) 0.77933(17) 0.0661(7) Uani 1 1 d . . . N8 N 0.4349(3) 0.2065(2) 0.73729(19) 0.0502(7) Uani 1 1 d . . . C9 C 0.3420(3) 0.1190(2) 0.68355(19) 0.0362(7) Uani 1 1 d . . . N9 N 0.2683(3) -0.1151(2) 0.52812(17) 0.0465(6) Uani 1 1 d . . . O9 O 0.1469(3) -0.1517(2) 0.48981(18) 0.0676(7) Uani 1 1 d . . . O10 O 0.3868(3) -0.1525(2) 0.51289(18) 0.0764(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 N1 0.0498(16) 0.0271(12) 0.0357(13) 0.0013(11) 0.0149(12) -0.0033(11) C1 0.0313(14) 0.0308(14) 0.0260(13) -0.0012(11) 0.0098(11) -0.0021(12) O1 0.0696(16) 0.0622(15) 0.0650(15) 0.0136(12) 0.0474(13) 0.0158(13) O2 0.0766(16) 0.0610(15) 0.0380(12) 0.0197(11) 0.0120(11) 0.0067(13) C2 0.0352(16) 0.0384(16) 0.0356(15) -0.0009(13) 0.0081(12) 0.0007(13) N2 0.074(2) 0.0547(17) 0.0627(17) 0.0240(15) 0.0327(15) 0.0323(15) N3 0.0421(15) 0.0416(15) 0.0524(16) -0.0077(13) 0.0169(13) 0.0023(12) O3 0.0827(19) 0.0707(17) 0.097(2) 0.0243(16) 0.0468(16) 0.0442(15) C3 0.0308(15) 0.0367(15) 0.0370(15) -0.0050(13) 0.0137(12) 0.0005(12) N4 0.0484(16) 0.0515(15) 0.0442(14) 0.0041(12) 0.0245(12) -0.0026(12) C4 0.0338(15) 0.0365(15) 0.0295(14) -0.0039(12) 0.0099(12) -0.0075(12) O4 0.0727(17) 0.0761(17) 0.0555(14) -0.0080(13) 0.0354(13) 0.0158(14) C5 0.0355(15) 0.0346(15) 0.0310(14) 0.0056(12) 0.0106(12) 0.0026(13) N5 0.0520(17) 0.0437(15) 0.0423(14) 0.0099(12) 0.0171(12) 0.0055(13) O5 0.0872(18) 0.0640(16) 0.0862(18) 0.0445(14) 0.0465(15) 0.0190(14) N6 0.0288(12) 0.0316(12) 0.0344(12) -0.0026(10) 0.0091(10) 0.0010(10) C6 0.0256(14) 0.0288(13) 0.0322(14) -0.0030(12) 0.0064(11) -0.0030(11) O6 0.0476(14) 0.0793(17) 0.0716(16) 0.0287(14) 0.0106(12) 0.0193(13) N7 0.0334(13) 0.0436(14) 0.0474(14) -0.0049(12) 0.0079(11) 0.0048(12) C7 0.0335(15) 0.0296(14) 0.0343(14) 0.0008(12) 0.0025(12) -0.0057(12) O7 0.0322(13) 0.0831(19) 0.134(2) -0.0413(17) 0.0121(14) -0.0149(13) C8 0.0406(17) 0.0290(14) 0.0361(15) -0.0001(12) 0.0046(13) 0.0051(13) O8 0.0458(14) 0.0635(15) 0.0897(18) -0.0401(14) 0.0127(13) -0.0061(12) N8 0.0336(15) 0.0494(16) 0.0684(18) -0.0168(14) 0.0110(13) -0.0050(12) C9 0.0302(15) 0.0356(15) 0.0430(16) -0.0017(13) 0.0070(12) 0.0002(13) N9 0.0565(17) 0.0363(14) 0.0435(15) -0.0030(12) -0.0019(13) 0.0115(13) O9 0.0675(17) 0.0505(14) 0.0780(17) -0.0260(12) -0.0087(14) -0.0006(12) O10 0.0715(18) 0.0851(19) 0.0702(16) -0.0302(14) 0.0046(13) 0.0383(15) _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 1.207(3) . ? N1 O1 1.223(3) . ? N1 C1 1.445(3) . ? C1 C6 1.378(3) . ? C1 C2 1.436(3) . ? C2 N2 1.320(3) . ? C2 C3 1.427(4) . ? N2 H2A 0.8600 . ? N2 H2B 0.8600 . ? N3 O3 1.220(3) . ? N3 O4 1.226(3) . ? N3 C3 1.443(3) . ? C3 C4 1.425(4) . ? N4 C4 1.323(3) . ? N4 H4A 0.8600 . ? N4 H4B 0.8600 . ? C4 C5 1.432(4) . ? C5 C6 1.380(3) . ? C5 N5 1.454(3) . ? N5 O6 1.214(3) . ? N5 O5 1.232(3) . ? N6 C7 1.363(3) . ? N6 C9 1.365(3) . ? N6 C6 1.441(3) . ? N7 C9 1.299(3) . ? N7 C8 1.359(3) . ? C7 C8 1.359(4) . ? C7 H7B 0.9300 . ? O7 N8 1.202(3) . ? C8 N9 1.436(3) . ? O8 N8 1.219(3) . ? N8 C9 1.440(4) . ? N9 O10 1.209(3) . ? N9 O9 1.221(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 O2 N1 O1 121.0(2) . . ? O2 N1 C1 120.6(2) . . ? O1 N1 C1 118.4(2) . . ? C6 C1 C2 120.6(2) . . ? C6 C1 N1 119.6(2) . . ? C2 C1 N1 119.8(2) . . ? N2 C2 C3 122.9(3) . . ? N2 C2 C1 120.1(2) . . ? C3 C2 C1 117.0(2) . . ? C2 N2 H2A 120.0 . . ? C2 N2 H2B 120.0 . . ? H2A N2 H2B 120.0 . . ? O3 N3 O4 119.4(3) . . ? O3 N3 C3 120.2(2) . . ? O4 N3 C3 120.4(3) . . ? C4 C3 C2 122.6(2) . . ? C4 C3 N3 118.4(2) . . ? C2 C3 N3 119.0(2) . . ? C4 N4 H4A 120.0 . . ? C4 N4 H4B 120.0 . . ? H4A N4 H4B 120.0 . . ? N4 C4 C3 123.2(2) . . ? N4 C4 C5 120.3(2) . . ? C3 C4 C5 116.5(2) . . ? C6 C5 C4 121.1(2) . . ? C6 C5 N5 118.9(2) . . ? C4 C5 N5 120.0(2) . . ? O6 N5 O5 122.4(3) . . ? O6 N5 C5 118.6(2) . . ? O5 N5 C5 118.9(3) . . ? C7 N6 C9 106.0(2) . . ? C7 N6 C6 122.7(2) . . ? C9 N6 C6 131.1(2) . . ? C1 C6 C5 121.8(2) . . ? C1 C6 N6 119.6(2) . . ? C5 C6 N6 117.8(2) . . ? C9 N7 C8 102.3(2) . . ? C8 C7 N6 104.1(2) . . ? C8 C7 H7B 127.9 . . ? N6 C7 H7B 127.9 . . ? C7 C8 N7 113.5(2) . . ? C7 C8 N9 125.2(3) . . ? N7 C8 N9 121.2(2) . . ? O7 N8 O8 125.3(3) . . ? O7 N8 C9 117.7(3) . . ? O8 N8 C9 117.0(2) . . ? N7 C9 N6 114.1(2) . . ? N7 C9 N8 123.9(3) . . ? N6 C9 N8 122.0(2) . . ? O10 N9 O9 124.6(3) . . ? O10 N9 C8 119.6(3) . . ? O9 N9 C8 115.8(3) . . ? 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 O2 N1 C1 C6 154.6(2) . . . . ? O1 N1 C1 C6 -25.8(4) . . . . ? O2 N1 C1 C2 -25.1(4) . . . . ? O1 N1 C1 C2 154.4(2) . . . . ? C6 C1 C2 N2 176.8(3) . . . . ? N1 C1 C2 N2 -3.4(4) . . . . ? C6 C1 C2 C3 -0.6(4) . . . . ? N1 C1 C2 C3 179.1(2) . . . . ? N2 C2 C3 C4 178.7(3) . . . . ? C1 C2 C3 C4 -3.9(4) . . . . ? N2 C2 C3 N3 -0.9(4) . . . . ? C1 C2 C3 N3 176.5(2) . . . . ? O3 N3 C3 C4 -173.2(3) . . . . ? O4 N3 C3 C4 7.6(4) . . . . ? O3 N3 C3 C2 6.5(4) . . . . ? O4 N3 C3 C2 -172.7(3) . . . . ? C2 C3 C4 N4 -172.8(3) . . . . ? N3 C3 C4 N4 6.9(4) . . . . ? C2 C3 C4 C5 7.4(4) . . . . ? N3 C3 C4 C5 -172.9(2) . . . . ? N4 C4 C5 C6 173.5(2) . . . . ? C3 C4 C5 C6 -6.7(4) . . . . ? N4 C4 C5 N5 -8.8(4) . . . . ? C3 C4 C5 N5 171.0(2) . . . . ? C6 C5 N5 O6 31.3(4) . . . . ? C4 C5 N5 O6 -146.4(3) . . . . ? C6 C5 N5 O5 -149.0(3) . . . . ? C4 C5 N5 O5 33.3(4) . . . . ? C2 C1 C6 C5 1.3(4) . . . . ? N1 C1 C6 C5 -178.5(2) . . . . ? C2 C1 C6 N6 171.0(2) . . . . ? N1 C1 C6 N6 -8.7(4) . . . . ? C4 C5 C6 C1 2.6(4) . . . . ? N5 C5 C6 C1 -175.1(2) . . . . ? C4 C5 C6 N6 -167.4(2) . . . . ? N5 C5 C6 N6 14.9(4) . . . . ? C7 N6 C6 C1 -86.0(3) . . . . ? C9 N6 C6 C1 88.7(3) . . . . ? C7 N6 C6 C5 84.2(3) . . . . ? C9 N6 C6 C5 -101.1(3) . . . . ? C9 N6 C7 C8 -0.2(3) . . . . ? C6 N6 C7 C8 175.7(2) . . . . ? N6 C7 C8 N7 0.6(3) . . . . ? N6 C7 C8 N9 -176.9(2) . . . . ? C9 N7 C8 C7 -0.8(3) . . . . ? C9 N7 C8 N9 176.8(2) . . . . ? C8 N7 C9 N6 0.7(3) . . . . ? C8 N7 C9 N8 -177.9(3) . . . . ? C7 N6 C9 N7 -0.3(3) . . . . ? C6 N6 C9 N7 -175.7(2) . . . . ? C7 N6 C9 N8 178.3(2) . . . . ? C6 N6 C9 N8 2.9(4) . . . . ? O7 N8 C9 N7 -0.8(4) . . . . ? O8 N8 C9 N7 178.2(3) . . . . ? O7 N8 C9 N6 -179.3(3) . . . . ? O8 N8 C9 N6 -0.3(4) . . . . ? C7 C8 N9 O10 -176.5(3) . . . . ? N7 C8 N9 O10 6.1(4) . . . . ? C7 C8 N9 O9 4.5(4) . . . . ? N7 C8 N9 O9 -172.9(3) . . . . ? _diffrn_measured_fraction_theta_max 1.000 _diffrn_reflns_theta_full 25.35 _diffrn_measured_fraction_theta_full 1.000 _refine_diff_density_max 0.192 _refine_diff_density_min -0.208 _refine_diff_density_rms 0.048 _database_code_depnum_ccdc_archive 'CCDC 888387' ####################################################################### # # Cambridge Crystallographic Data Centre # CCDC # ####################################################################### # # This CIF contains data from an original supplementary publication # deposited with the CCDC, and may include chemical, crystal, # experimental, refinement, atomic coordinates, # anisotropic displacement parameters and molecular geometry data, # as required by the journal to which it was submitted. # # This CIF is provided on the understanding that it is used for bona # fide research purposes only. It may contain copyright material # of the CCDC or of third parties, and may not be copied or further # disseminated in any form, whether machine-readable or not, # except for the purpose of generating routine backup copies # on your local computer system. # # For further information on the CCDC, data deposition and # data retrieval see: # www.ccdc.cam.ac.uk # # Bona fide researchers may freely download Mercury and enCIFer # from this site to visualise CIF-encoded structures and # to carry out CIF format checking respectively. # data_x2 #TrackingRef 'X45piccl ccdc.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C9 H3 N7 O10' _chemical_formula_weight 369.18 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 0.0000 '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 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Orthorhombic _symmetry_space_group_name_H-M P212121 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, -y, z+1/2' 'x+1/2, -y+1/2, -z' '-x, y+1/2, -z+1/2' _cell_length_a 8.2370(16) _cell_length_b 12.791(3) _cell_length_c 12.916(3) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 1360.8(5) _cell_formula_units_Z 4 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 25 _cell_measurement_theta_min 9 _cell_measurement_theta_max 13 _exptl_crystal_description ? _exptl_crystal_colour ? _exptl_crystal_size_max 0.30 _exptl_crystal_size_mid 0.20 _exptl_crystal_size_min 0.10 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.802 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 744 _exptl_absorpt_coefficient_mu 0.167 _exptl_absorpt_correction_type psi-scan _exptl_absorpt_correction_T_min 0.9517 _exptl_absorpt_correction_T_max 0.9835 _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 293(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 'Nonius CAD4' _diffrn_measurement_method \w/2\q _diffrn_detector_area_resol_mean ? _diffrn_standards_number 3 _diffrn_standards_interval_count 200 _diffrn_standards_interval_time 2h _diffrn_standards_decay_% 1 _diffrn_reflns_number 2774 _diffrn_reflns_av_R_equivalents 0.0440 _diffrn_reflns_av_sigmaI/netI 0.0494 _diffrn_reflns_limit_h_min 0 _diffrn_reflns_limit_h_max 9 _diffrn_reflns_limit_k_min 0 _diffrn_reflns_limit_k_max 15 _diffrn_reflns_limit_l_min -15 _diffrn_reflns_limit_l_max 15 _diffrn_reflns_theta_min 2.24 _diffrn_reflns_theta_max 25.37 _reflns_number_total 1448 _reflns_number_gt 1090 _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^)+(0.1000P)^2^+0.4000P] 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 1448 _refine_ls_number_parameters 217 _refine_ls_number_restraints 1 _refine_ls_R_factor_all 0.0808 _refine_ls_R_factor_gt 0.0608 _refine_ls_wR_factor_ref 0.1594 _refine_ls_wR_factor_gt 0.1465 _refine_ls_goodness_of_fit_ref 1.002 _refine_ls_restrained_S_all 1.024 _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 0.9477(6) 0.0154(3) 0.6332(4) 0.0322(11) Uani 1 1 d . . . O1 O 0.8534(7) 0.0756(5) 0.3788(4) 0.0688(16) Uani 1 1 d . . . C1 C 0.8856(9) 0.0613(5) 0.7157(4) 0.0398(15) Uani 1 1 d . . . H1B H 0.8976 0.0371 0.7831 0.048 Uiso 1 1 calc R . . N2 N 0.8011(6) 0.1491(4) 0.6888(3) 0.0282(10) Uani 1 1 d . . . C2 C 0.8948(7) 0.0723(4) 0.5533(4) 0.0298(12) Uani 1 1 d . . . O2 O 1.0283(7) -0.0315(4) 0.4378(4) 0.0644(15) Uani 1 1 d . . . N3 N 0.9248(7) 0.0366(4) 0.4489(4) 0.0423(13) Uani 1 1 d . . . C3 C 0.8000(7) 0.1535(4) 0.5832(4) 0.0309(12) Uani 1 1 d . . . O3 O 0.7799(9) 0.2691(6) 0.4560(6) 0.099 Uani 1 1 d . . . N4 N 0.7193(8) 0.2420(5) 0.5268(5) 0.052 Uani 1 1 d . . . C4 C 0.7104(7) 0.2125(4) 0.7616(4) 0.0304(13) Uani 1 1 d . . . O4 O 0.6547(8) 0.2913(5) 0.5738(5) 0.092 Uani 1 1 d D . . N5 N 0.9739(6) 0.2953(4) 0.8023(4) 0.0356(12) Uani 1 1 d . . . C5 C 0.7983(7) 0.2851(4) 0.8200(4) 0.0278(12) Uani 1 1 d . . . O5 O 1.0197(7) 0.3243(4) 0.7166(4) 0.0664(16) Uani 1 1 d . . . O6 O 1.0630(5) 0.2763(4) 0.8759(4) 0.0549(13) Uani 1 1 d . . . N6 N 0.4878(7) 0.3991(4) 0.9911(4) 0.0412(12) Uani 1 1 d . . . C6 C 0.7278(7) 0.3470(4) 0.8933(4) 0.0305(13) Uani 1 1 d . . . H6A H 0.7890 0.3944 0.9314 0.037 Uiso 1 1 calc R . . O7 O 0.5708(7) 0.4582(4) 1.0413(4) 0.0558(13) Uani 1 1 d . . . N7 N 0.4441(6) 0.1257(4) 0.7288(4) 0.0403(12) Uani 1 1 d . . . C7 C 0.5662(7) 0.3372(4) 0.9086(4) 0.0305(12) Uani 1 1 d . . . O8 O 0.3429(6) 0.3901(4) 1.0020(3) 0.0556(13) Uani 1 1 d . . . C8 C 0.4709(7) 0.2672(5) 0.8544(4) 0.0359(14) Uani 1 1 d . . . H8A H 0.3601 0.2635 0.8677 0.043 Uiso 1 1 calc R . . O9 O 0.2974(7) 0.1272(5) 0.7475(5) 0.0696(16) Uani 1 1 d . . . C9 C 0.5393(7) 0.2029(4) 0.7805(4) 0.0310(13) Uani 1 1 d . . . O10 O 0.5062(7) 0.0623(4) 0.6728(4) 0.0639(15) 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 N1 0.038(3) 0.028(2) 0.031(2) -0.007(2) 0.006(2) 0.004(2) O1 0.068(3) 0.103(4) 0.036(2) -0.002(3) -0.006(3) 0.013(3) C1 0.059(4) 0.031(3) 0.030(3) -0.004(2) -0.001(3) 0.016(3) N2 0.028(2) 0.029(2) 0.028(2) 0.000(2) 0.006(2) 0.007(2) C2 0.023(3) 0.033(3) 0.033(3) -0.006(2) 0.000(2) -0.002(3) O2 0.081(4) 0.068(3) 0.045(3) -0.016(3) 0.015(3) 0.023(3) N3 0.057(4) 0.036(3) 0.034(3) -0.003(2) 0.005(3) -0.013(3) C3 0.025(3) 0.033(3) 0.034(3) 0.001(3) -0.006(3) 0.005(3) O3 0.099 0.099 0.099 0.000 0.000 0.000 N4 0.052 0.052 0.052 0.000 0.000 0.000 C4 0.027(3) 0.033(3) 0.031(3) 0.004(2) -0.006(2) 0.001(3) O4 0.092 0.092 0.092 0.000 0.000 0.000 N5 0.033(3) 0.027(3) 0.047(3) -0.010(2) 0.010(3) -0.004(2) C5 0.023(3) 0.032(3) 0.028(3) -0.004(2) 0.006(2) 0.003(2) O5 0.062(3) 0.072(4) 0.065(3) -0.001(3) 0.026(3) -0.023(3) O6 0.030(2) 0.047(3) 0.087(4) 0.006(3) -0.006(3) 0.007(2) N6 0.047(3) 0.036(3) 0.040(3) 0.004(2) 0.010(3) -0.001(3) C6 0.032(3) 0.020(3) 0.039(3) 0.000(2) -0.004(2) -0.005(2) O7 0.066(3) 0.049(3) 0.053(3) -0.019(2) -0.001(3) -0.001(3) N7 0.035(3) 0.047(3) 0.040(3) -0.003(3) -0.005(2) -0.012(3) C7 0.028(3) 0.031(3) 0.032(3) 0.000(2) 0.003(2) 0.008(2) O8 0.047(3) 0.072(3) 0.048(3) -0.016(3) 0.009(2) 0.011(3) C8 0.033(3) 0.043(3) 0.031(3) -0.001(3) 0.008(3) 0.008(3) O9 0.053(3) 0.074(4) 0.083(4) -0.019(3) -0.017(3) -0.013(3) C9 0.032(3) 0.022(3) 0.039(3) 0.004(2) 0.001(3) 0.002(2) O10 0.062(3) 0.069(3) 0.061(3) -0.034(3) 0.008(3) -0.017(3) _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 C1 1.319(7) . ? N1 C2 1.337(7) . ? O1 N3 1.190(7) . ? C1 N2 1.366(7) . ? C1 H1B 0.9300 . ? N2 C3 1.366(7) . ? N2 C4 1.449(7) . ? C2 C3 1.356(8) . ? C2 N3 1.445(7) . ? O2 N3 1.227(7) . ? C3 N4 1.500(8) . ? O3 N4 1.098(7) . ? N4 O4 1.024(7) . ? C4 C5 1.398(8) . ? C4 C9 1.436(8) . ? N5 O6 1.224(7) . ? N5 O5 1.227(6) . ? N5 C5 1.470(7) . ? C5 C6 1.364(8) . ? N6 O7 1.207(7) . ? N6 O8 1.207(7) . ? N6 C7 1.477(7) . ? C6 C7 1.352(8) . ? C6 H6A 0.9300 . ? N7 O10 1.201(7) . ? N7 O9 1.233(7) . ? N7 C9 1.426(7) . ? C7 C8 1.382(8) . ? C8 C9 1.380(8) . ? C8 H8A 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 C1 N1 C2 104.7(4) . . ? N1 C1 N2 111.0(5) . . ? N1 C1 H1B 124.5 . . ? N2 C1 H1B 124.5 . . ? C1 N2 C3 106.9(5) . . ? C1 N2 C4 123.9(5) . . ? C3 N2 C4 128.4(5) . . ? N1 C2 C3 112.7(5) . . ? N1 C2 N3 119.5(5) . . ? C3 C2 N3 127.3(5) . . ? O1 N3 O2 123.5(5) . . ? O1 N3 C2 119.6(5) . . ? O2 N3 C2 116.9(5) . . ? C2 C3 N2 104.4(5) . . ? C2 C3 N4 134.0(5) . . ? N2 C3 N4 121.3(5) . . ? O4 N4 O3 122.3(8) . . ? O4 N4 C3 114.0(6) . . ? O3 N4 C3 116.2(7) . . ? C5 C4 C9 118.3(5) . . ? C5 C4 N2 117.0(5) . . ? C9 C4 N2 124.7(5) . . ? O6 N5 O5 125.2(5) . . ? O6 N5 C5 116.8(5) . . ? O5 N5 C5 118.0(5) . . ? C6 C5 C4 122.6(5) . . ? C6 C5 N5 118.4(5) . . ? C4 C5 N5 119.0(5) . . ? O7 N6 O8 123.9(6) . . ? O7 N6 C7 118.4(5) . . ? O8 N6 C7 117.7(5) . . ? C7 C6 C5 117.9(5) . . ? C7 C6 H6A 121.1 . . ? C5 C6 H6A 121.1 . . ? O10 N7 O9 123.1(6) . . ? O10 N7 C9 121.0(5) . . ? O9 N7 C9 115.9(6) . . ? C6 C7 C8 123.0(5) . . ? C6 C7 N6 119.1(5) . . ? C8 C7 N6 117.7(5) . . ? C9 C8 C7 120.3(5) . . ? C9 C8 H8A 119.8 . . ? C7 C8 H8A 119.8 . . ? C8 C9 N7 120.8(5) . . ? C8 C9 C4 117.8(5) . . ? N7 C9 C4 121.3(5) . . ? 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 C2 N1 C1 N2 -3.0(7) . . . . ? N1 C1 N2 C3 4.9(7) . . . . ? N1 C1 N2 C4 175.9(5) . . . . ? C1 N1 C2 C3 -0.1(7) . . . . ? C1 N1 C2 N3 -172.8(6) . . . . ? N1 C2 N3 O1 166.1(6) . . . . ? C3 C2 N3 O1 -5.5(9) . . . . ? N1 C2 N3 O2 -16.0(8) . . . . ? C3 C2 N3 O2 172.4(6) . . . . ? N1 C2 C3 N2 3.0(6) . . . . ? N3 C2 C3 N2 175.1(6) . . . . ? N1 C2 C3 N4 176.3(6) . . . . ? N3 C2 C3 N4 -11.7(10) . . . . ? C1 N2 C3 C2 -4.6(6) . . . . ? C4 N2 C3 C2 -175.0(5) . . . . ? C1 N2 C3 N4 -178.9(5) . . . . ? C4 N2 C3 N4 10.7(9) . . . . ? C2 C3 N4 O4 -179.9(7) . . . . ? N2 C3 N4 O4 -7.5(10) . . . . ? C2 C3 N4 O3 -29.3(10) . . . . ? N2 C3 N4 O3 143.0(7) . . . . ? C1 N2 C4 C5 81.6(7) . . . . ? C3 N2 C4 C5 -109.5(7) . . . . ? C1 N2 C4 C9 -95.8(7) . . . . ? C3 N2 C4 C9 73.1(8) . . . . ? C9 C4 C5 C6 -0.4(8) . . . . ? N2 C4 C5 C6 -177.9(5) . . . . ? C9 C4 C5 N5 179.5(5) . . . . ? N2 C4 C5 N5 2.0(8) . . . . ? O6 N5 C5 C6 60.9(7) . . . . ? O5 N5 C5 C6 -117.5(6) . . . . ? O6 N5 C5 C4 -119.0(6) . . . . ? O5 N5 C5 C4 62.6(7) . . . . ? C4 C5 C6 C7 -0.4(9) . . . . ? N5 C5 C6 C7 179.8(5) . . . . ? C5 C6 C7 C8 0.5(9) . . . . ? C5 C6 C7 N6 176.9(5) . . . . ? O7 N6 C7 C6 1.3(8) . . . . ? O8 N6 C7 C6 178.8(6) . . . . ? O7 N6 C7 C8 177.8(5) . . . . ? O8 N6 C7 C8 -4.7(8) . . . . ? C6 C7 C8 C9 0.1(9) . . . . ? N6 C7 C8 C9 -176.3(5) . . . . ? C7 C8 C9 N7 175.9(5) . . . . ? C7 C8 C9 C4 -0.8(8) . . . . ? O10 N7 C9 C8 -171.9(6) . . . . ? O9 N7 C9 C8 6.3(8) . . . . ? O10 N7 C9 C4 4.7(8) . . . . ? O9 N7 C9 C4 -177.1(6) . . . . ? C5 C4 C9 C8 1.0(8) . . . . ? N2 C4 C9 C8 178.3(5) . . . . ? C5 C4 C9 N7 -175.7(5) . . . . ? N2 C4 C9 N7 1.6(8) . . . . ? _diffrn_measured_fraction_theta_max 1.000 _diffrn_reflns_theta_full 25.37 _diffrn_measured_fraction_theta_full 1.000 _refine_diff_density_max 0.339 _refine_diff_density_min -0.577 _refine_diff_density_rms 0.071 _database_code_depnum_ccdc_archive 'CCDC 884548' ####################################################################### # # Cambridge Crystallographic Data Centre # CCDC # ####################################################################### # # This CIF contains data from an original supplementary publication # deposited with the CCDC, and may include chemical, crystal, # experimental, refinement, atomic coordinates, # anisotropic displacement parameters and molecular geometry data, # as required by the journal to which it was submitted. # # This CIF is provided on the understanding that it is used for bona # fide research purposes only. It may contain copyright material # of the CCDC or of third parties, and may not be copied or further # disseminated in any form, whether machine-readable or not, # except for the purpose of generating routine backup copies # on your local computer system. # # For further information on the CCDC, data deposition and # data retrieval see: # www.ccdc.cam.ac.uk # # Bona fide researchers may freely download Mercury and enCIFer # from this site to visualise CIF-encoded structures and # to carry out CIF format checking respectively. # data_x3 #TrackingRef 'X45picnh2 CCDC.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C9 H4 N8 O10' _chemical_formula_weight 384.20 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 0.0000 '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 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Orthorhombic _symmetry_space_group_name_H-M P212121 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, -y, z+1/2' 'x+1/2, -y+1/2, -z' '-x, y+1/2, -z+1/2' _cell_length_a 8.4941(7) _cell_length_b 12.7651(10) _cell_length_c 13.3699(12) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 1449.7(2) _cell_formula_units_Z 4 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 25 _cell_measurement_theta_min 9 _cell_measurement_theta_max 12 _exptl_crystal_description ? _exptl_crystal_colour ? _exptl_crystal_size_max 0.20 _exptl_crystal_size_mid 0.10 _exptl_crystal_size_min 0.10 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.760 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 776 _exptl_absorpt_coefficient_mu 0.162 _exptl_absorpt_correction_type psi-scan _exptl_absorpt_correction_T_min 0.9683 _exptl_absorpt_correction_T_max 0.9840 _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 293(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 'Nonius CAD4' _diffrn_measurement_method \w/2\q _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 2560 _diffrn_reflns_av_R_equivalents 0.1131 _diffrn_reflns_av_sigmaI/netI 0.1271 _diffrn_reflns_limit_h_min -10 _diffrn_reflns_limit_h_max 10 _diffrn_reflns_limit_k_min 0 _diffrn_reflns_limit_k_max 15 _diffrn_reflns_limit_l_min 0 _diffrn_reflns_limit_l_max 15 _diffrn_reflns_theta_min 2.84 _diffrn_reflns_theta_max 25.31 _reflns_number_total 1491 _reflns_number_gt 711 _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^)+(0.0600P)^2^+0.0000P] 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 1491 _refine_ls_number_parameters 226 _refine_ls_number_restraints 6 _refine_ls_R_factor_all 0.1468 _refine_ls_R_factor_gt 0.0780 _refine_ls_wR_factor_ref 0.1809 _refine_ls_wR_factor_gt 0.1453 _refine_ls_goodness_of_fit_ref 1.044 _refine_ls_restrained_S_all 1.048 _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 0.4805(9) 0.0739(5) 0.5883(6) 0.045(2) Uani 1 1 d . . . O1 O 0.2812(11) 0.3412(5) 0.7625(5) 0.082(3) Uani 1 1 d U . . C1 C 0.3891(12) 0.0519(8) 0.6731(7) 0.057(3) Uani 1 1 d . . . H1A H 0.3670 -0.0152 0.6962 0.068 Uiso 1 1 calc R . . N2 N 0.3383(10) 0.1390(6) 0.7160(5) 0.051(2) Uani 1 1 d . . . C2 C 0.4028(10) 0.2197(6) 0.6617(6) 0.039(2) Uani 1 1 d . . . O2 O 0.4223(13) 0.3941(6) 0.6387(10) 0.135(4) Uani 1 1 d . . . N3 N 0.3654(10) 0.3270(6) 0.6906(6) 0.050(2) Uani 1 1 d U . . C3 C 0.4880(9) 0.1839(5) 0.5857(7) 0.037(2) Uani 1 1 d . . . O3 O 0.6509(12) 0.3074(8) 0.5109(7) 0.142 Uani 1 1 d D . . C4 C 0.5681(12) -0.0038(6) 0.5298(7) 0.046(2) Uani 1 1 d . . . N4 N 0.5655(13) 0.2281(8) 0.5028(8) 0.087 Uani 1 1 d . . . O4 O 0.5813(14) 0.1908(8) 0.4242(8) 0.139 Uani 1 1 d . . . C5 C 0.7220(10) -0.0297(7) 0.5487(7) 0.040(2) Uani 1 1 d U . . O5 O 0.7603(11) 0.0964(7) 0.6831(9) 0.116(4) Uani 1 1 d . . . N5 N 0.8194(10) 0.0265(7) 0.6271(7) 0.059(2) Uani 1 1 d . . . O6 O 0.9496(9) -0.0020(6) 0.6450(6) 0.087(3) Uani 1 1 d . . . C6 C 0.7949(12) -0.1044(8) 0.4933(7) 0.058(3) Uani 1 1 d U . . H6A H 0.9011 -0.1176 0.5045 0.069 Uiso 1 1 calc R . . N6 N 0.8079(12) -0.2422(6) 0.3650(6) 0.054(2) Uani 1 1 d . . . O7 O 0.9472(9) -0.2536(5) 0.3882(6) 0.072(2) Uani 1 1 d . . . N8 N 0.3257(11) -0.0344(8) 0.4351(7) 0.063(2) Uani 1 1 d U . . C7 C 0.7153(11) -0.1627(7) 0.4195(6) 0.045(2) Uani 1 1 d U . . O8 O 0.7387(9) -0.2953(5) 0.3039(5) 0.076(2) Uani 1 1 d . . . C8 C 0.5580(11) -0.1422(6) 0.3950(6) 0.042(2) Uani 1 1 d . . . N7 N 0.4716(9) -0.1925(6) 0.3268(6) 0.057(2) Uani 1 1 d . . . H7A H 0.5122 -0.2429 0.2928 0.069 Uiso 1 1 calc R . . H7B H 0.3753 -0.1744 0.3168 0.069 Uiso 1 1 calc R . . C9 C 0.4887(11) -0.0574(7) 0.4549(7) 0.047(2) Uani 1 1 d U . . O9 O 0.2260(10) -0.0852(8) 0.4737(8) 0.102(3) Uani 1 1 d . . . O10 O 0.3024(10) 0.0303(7) 0.3673(8) 0.119(4) 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 N1 0.046(5) 0.033(4) 0.056(5) 0.002(4) -0.009(4) -0.009(4) O1 0.120(7) 0.053(4) 0.072(5) -0.013(4) 0.011(5) 0.024(5) C1 0.078(8) 0.057(6) 0.035(5) -0.009(5) 0.010(6) -0.002(6) N2 0.069(6) 0.056(5) 0.030(4) -0.008(4) 0.001(4) 0.001(5) C2 0.041(5) 0.038(5) 0.039(5) -0.011(4) -0.007(5) 0.001(4) O2 0.149(9) 0.053(5) 0.204(11) -0.003(6) 0.073(10) -0.001(6) N3 0.051(5) 0.044(5) 0.054(5) -0.005(4) -0.002(4) 0.002(4) C3 0.034(5) 0.021(4) 0.055(5) 0.004(4) -0.002(5) -0.009(4) O3 0.142 0.142 0.142 0.000 0.000 0.000 C4 0.055(6) 0.029(5) 0.054(6) 0.006(4) 0.009(5) -0.008(5) N4 0.087 0.087 0.087 0.000 0.000 0.000 O4 0.139 0.139 0.139 0.000 0.000 0.000 C5 0.035(5) 0.037(5) 0.049(5) -0.011(4) -0.017(4) -0.005(4) O5 0.090(7) 0.093(6) 0.167(9) -0.065(7) -0.028(7) 0.041(6) N5 0.049(6) 0.049(5) 0.080(6) 0.001(5) -0.025(5) 0.000(5) O6 0.054(5) 0.113(7) 0.094(6) -0.025(5) -0.017(5) -0.002(5) C6 0.035(5) 0.075(7) 0.062(6) -0.001(5) 0.004(5) 0.013(5) N6 0.072(6) 0.053(5) 0.038(5) 0.007(4) 0.011(5) 0.013(5) O7 0.062(5) 0.068(5) 0.085(5) -0.001(5) 0.017(4) 0.016(4) N8 0.053(5) 0.068(6) 0.067(6) -0.014(5) -0.003(5) -0.007(5) C7 0.053(6) 0.043(5) 0.039(4) 0.000(4) 0.007(5) 0.010(5) O8 0.097(6) 0.069(5) 0.062(5) -0.022(4) -0.017(4) 0.033(5) C8 0.066(6) 0.024(4) 0.036(5) 0.004(4) 0.006(5) 0.000(5) N7 0.051(5) 0.060(5) 0.061(5) -0.021(5) -0.012(4) 0.010(4) C9 0.042(5) 0.053(6) 0.045(5) -0.007(5) 0.008(5) 0.020(5) O9 0.043(5) 0.141(8) 0.123(7) 0.023(7) -0.003(5) -0.018(6) O10 0.087(7) 0.108(7) 0.160(10) 0.062(8) -0.011(7) 0.012(6) _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 C1 1.402(11) . ? N1 C3 1.405(9) . ? N1 C4 1.467(11) . ? O1 N3 1.212(10) . ? C1 N2 1.323(11) . ? C1 H1A 0.9300 . ? N2 C2 1.375(10) . ? C2 C3 1.329(11) . ? C2 N3 1.457(10) . ? O2 N3 1.204(11) . ? C3 N4 1.406(13) . ? O3 N4 1.250(12) . ? C4 C5 1.372(12) . ? C4 C9 1.387(12) . ? N4 O4 1.162(12) . ? C5 C6 1.357(12) . ? C5 N5 1.516(11) . ? O5 N5 1.268(12) . ? N5 O6 1.188(10) . ? C6 C7 1.409(13) . ? C6 H6A 0.9300 . ? N6 O8 1.214(10) . ? N6 O7 1.232(11) . ? N6 C7 1.476(11) . ? N8 O9 1.185(11) . ? N8 O10 1.241(11) . ? N8 C9 1.440(12) . ? C7 C8 1.400(12) . ? C8 N7 1.335(10) . ? C8 C9 1.470(11) . ? N7 H7A 0.8600 . ? N7 H7B 0.8600 . ? 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 C1 N1 C3 104.2(8) . . ? C1 N1 C4 125.2(7) . . ? C3 N1 C4 129.8(8) . . ? N2 C1 N1 111.3(9) . . ? N2 C1 H1A 124.4 . . ? N1 C1 H1A 124.4 . . ? C1 N2 C2 105.7(7) . . ? C3 C2 N2 111.2(7) . . ? C3 C2 N3 130.2(8) . . ? N2 C2 N3 118.5(8) . . ? O2 N3 O1 126.0(9) . . ? O2 N3 C2 115.3(8) . . ? O1 N3 C2 118.7(9) . . ? C2 C3 N1 107.5(8) . . ? C2 C3 N4 136.0(8) . . ? N1 C3 N4 116.2(8) . . ? C5 C4 C9 118.6(9) . . ? C5 C4 N1 123.2(9) . . ? C9 C4 N1 118.2(8) . . ? O4 N4 O3 110.0(12) . . ? O4 N4 C3 127.0(11) . . ? O3 N4 C3 121.9(11) . . ? C6 C5 C4 120.2(9) . . ? C6 C5 N5 117.5(8) . . ? C4 C5 N5 122.3(8) . . ? O6 N5 O5 117.7(10) . . ? O6 N5 C5 120.1(9) . . ? O5 N5 C5 121.7(9) . . ? C5 C6 C7 122.3(9) . . ? C5 C6 H6A 118.8 . . ? C7 C6 H6A 118.8 . . ? O8 N6 O7 124.6(9) . . ? O8 N6 C7 117.3(9) . . ? O7 N6 C7 118.0(9) . . ? O9 N8 O10 124.6(10) . . ? O9 N8 C9 119.6(10) . . ? O10 N8 C9 115.0(10) . . ? C8 C7 C6 121.6(8) . . ? C8 C7 N6 121.4(9) . . ? C6 C7 N6 116.9(9) . . ? N7 C8 C7 126.5(8) . . ? N7 C8 C9 120.4(8) . . ? C7 C8 C9 113.1(8) . . ? C8 N7 H7A 120.0 . . ? C8 N7 H7B 120.0 . . ? H7A N7 H7B 120.0 . . ? C4 C9 N8 120.0(8) . . ? C4 C9 C8 124.1(9) . . ? N8 C9 C8 115.8(9) . . ? 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 C3 N1 C1 N2 2.9(11) . . . . ? C4 N1 C1 N2 173.3(8) . . . . ? N1 C1 N2 C2 -2.8(11) . . . . ? C1 N2 C2 C3 1.6(11) . . . . ? C1 N2 C2 N3 179.0(8) . . . . ? C3 C2 N3 O2 -1.3(15) . . . . ? N2 C2 N3 O2 -178.2(10) . . . . ? C3 C2 N3 O1 178.2(9) . . . . ? N2 C2 N3 O1 1.3(12) . . . . ? N2 C2 C3 N1 0.1(11) . . . . ? N3 C2 C3 N1 -176.9(8) . . . . ? N2 C2 C3 N4 172.6(10) . . . . ? N3 C2 C3 N4 -4.4(18) . . . . ? C1 N1 C3 C2 -1.7(10) . . . . ? C4 N1 C3 C2 -171.6(8) . . . . ? C1 N1 C3 N4 -175.9(8) . . . . ? C4 N1 C3 N4 14.3(14) . . . . ? C1 N1 C4 C5 -91.3(11) . . . . ? C3 N1 C4 C5 76.6(12) . . . . ? C1 N1 C4 C9 85.5(11) . . . . ? C3 N1 C4 C9 -106.6(11) . . . . ? C2 C3 N4 O4 -146.6(13) . . . . ? N1 C3 N4 O4 25.4(18) . . . . ? C2 C3 N4 O3 46.1(18) . . . . ? N1 C3 N4 O3 -141.9(10) . . . . ? C9 C4 C5 C6 1.5(13) . . . . ? N1 C4 C5 C6 178.2(7) . . . . ? C9 C4 C5 N5 178.4(8) . . . . ? N1 C4 C5 N5 -4.9(13) . . . . ? C6 C5 N5 O6 -7.1(14) . . . . ? C4 C5 N5 O6 175.9(10) . . . . ? C6 C5 N5 O5 -179.1(11) . . . . ? C4 C5 N5 O5 3.9(14) . . . . ? C4 C5 C6 C7 -4.0(15) . . . . ? N5 C5 C6 C7 179.0(8) . . . . ? C5 C6 C7 C8 3.8(14) . . . . ? C5 C6 C7 N6 -179.6(8) . . . . ? O8 N6 C7 C8 -6.0(12) . . . . ? O7 N6 C7 C8 177.6(8) . . . . ? O8 N6 C7 C6 177.4(8) . . . . ? O7 N6 C7 C6 0.9(12) . . . . ? C6 C7 C8 N7 -179.9(9) . . . . ? N6 C7 C8 N7 3.7(13) . . . . ? C6 C7 C8 C9 -1.1(11) . . . . ? N6 C7 C8 C9 -177.5(7) . . . . ? C5 C4 C9 N8 178.2(9) . . . . ? N1 C4 C9 N8 1.3(12) . . . . ? C5 C4 C9 C8 1.2(13) . . . . ? N1 C4 C9 C8 -175.7(8) . . . . ? O9 N8 C9 C4 -94.2(13) . . . . ? O10 N8 C9 C4 94.8(11) . . . . ? O9 N8 C9 C8 83.1(12) . . . . ? O10 N8 C9 C8 -88.0(11) . . . . ? N7 C8 C9 C4 177.5(8) . . . . ? C7 C8 C9 C4 -1.4(12) . . . . ? N7 C8 C9 N8 0.4(12) . . . . ? C7 C8 C9 N8 -178.5(8) . . . . ? _diffrn_measured_fraction_theta_max 0.970 _diffrn_reflns_theta_full 25.31 _diffrn_measured_fraction_theta_full 0.970 _refine_diff_density_max 0.405 _refine_diff_density_min -0.318 _refine_diff_density_rms 0.068 _database_code_depnum_ccdc_archive 'CCDC 884549' ####################################################################### # # Cambridge Crystallographic Data Centre # CCDC # ####################################################################### # # This CIF contains data from an original supplementary publication # deposited with the CCDC, and may include chemical, crystal, # experimental, refinement, atomic coordinates, # anisotropic displacement parameters and molecular geometry data, # as required by the journal to which it was submitted. # # This CIF is provided on the understanding that it is used for bona # fide research purposes only. It may contain copyright material # of the CCDC or of third parties, and may not be copied or further # disseminated in any form, whether machine-readable or not, # except for the purpose of generating routine backup copies # on your local computer system. # # For further information on the CCDC, data deposition and # data retrieval see: # www.ccdc.cam.ac.uk # # Bona fide researchers may freely download Mercury and enCIFer # from this site to visualise CIF-encoded structures and # to carry out CIF format checking respectively. # data_x #TrackingRef 'X4,5 eran ccdc.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C9 H5 N9 O10' _chemical_formula_weight 399.22 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 0.0000 '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 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Orthorhombic _symmetry_space_group_name_H-M P212121 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 9.1580(18) _cell_length_b 12.318(3) _cell_length_c 12.862(3) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 1450.9(5) _cell_formula_units_Z 4 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 25 _cell_measurement_theta_min 10 _cell_measurement_theta_max 13 _exptl_crystal_description ? _exptl_crystal_colour ? _exptl_crystal_size_max 0.30 _exptl_crystal_size_mid 0.20 _exptl_crystal_size_min 0.10 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.828 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 808 _exptl_absorpt_coefficient_mu 0.168 _exptl_absorpt_correction_type psi-scan _exptl_absorpt_correction_T_min 0.9514 _exptl_absorpt_correction_T_max 0.9834 _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 293(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 'Nonius CAD4' _diffrn_measurement_method \w/2\q _diffrn_detector_area_resol_mean ? _diffrn_standards_number 3 _diffrn_standards_interval_count 200 _diffrn_standards_interval_time 2h _diffrn_standards_decay_% 1 _diffrn_reflns_number 2925 _diffrn_reflns_av_R_equivalents 0.0562 _diffrn_reflns_av_sigmaI/netI 0.0608 _diffrn_reflns_limit_h_min 0 _diffrn_reflns_limit_h_max 11 _diffrn_reflns_limit_k_min 0 _diffrn_reflns_limit_k_max 14 _diffrn_reflns_limit_l_min -15 _diffrn_reflns_limit_l_max 15 _diffrn_reflns_theta_min 2.29 _diffrn_reflns_theta_max 25.37 _reflns_number_total 1530 _reflns_number_gt 1084 _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^)+(0.1000P)^2^+0.0000P] 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 1530 _refine_ls_number_parameters 253 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0823 _refine_ls_R_factor_gt 0.0535 _refine_ls_wR_factor_ref 0.1575 _refine_ls_wR_factor_gt 0.1381 _refine_ls_goodness_of_fit_ref 1.003 _refine_ls_restrained_S_all 1.003 _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 C0 C 0.2297(5) 0.3002(4) 0.8150(4) 0.0371(13) Uani 1 1 d . . . C1 C 0.1556(7) 0.0749(4) 0.7020(4) 0.0452(14) Uani 1 1 d . . . H1A H 0.1389 0.0478 0.7684 0.054 Uiso 1 1 calc R . . N1 N 0.1053(5) 0.0299(4) 0.6169(4) 0.0469(12) Uani 1 1 d . . . O1 O 0.0691(6) -0.0248(4) 0.4141(4) 0.0688(14) Uani 1 1 d . . . N2 N 0.2355(5) 0.1662(3) 0.6817(3) 0.0367(11) Uani 1 1 d . . . C2 C 0.1576(6) 0.0925(4) 0.5376(4) 0.0380(12) Uani 1 1 d . . . O2 O 0.1529(7) 0.1292(5) 0.3619(3) 0.0899(18) Uani 1 1 d . . . C3 C 0.2371(6) 0.1767(4) 0.5729(4) 0.0378(12) Uani 1 1 d . . . N3 N 0.1241(6) 0.0638(4) 0.4291(4) 0.0496(12) Uani 1 1 d . . . O3 O 0.3750(9) 0.2467(7) 0.4427(5) 0.138(3) Uani 1 1 d . . . C4 C 0.3125(6) 0.2300(4) 0.7582(4) 0.0341(12) Uani 1 1 d . . . N4 N 0.3164(6) 0.2660(5) 0.5236(4) 0.0544(14) Uani 1 1 d . . . O4 O 0.3248(8) 0.3471(4) 0.5711(4) 0.0865(17) Uani 1 1 d . . . C5 C 0.4611(6) 0.2177(4) 0.7777(4) 0.0367(13) Uani 1 1 d . . . N5 N 0.5462(6) 0.1397(5) 0.7189(4) 0.0528(13) Uani 1 1 d . . . O5 O 0.4987(7) 0.1040(7) 0.6401(5) 0.135(3) Uani 1 1 d . . . C6 C 0.5279(6) 0.2826(4) 0.8574(4) 0.0400(14) Uani 1 1 d . . . N6 N 0.6730(5) 0.2790(5) 0.8734(4) 0.0588(15) Uani 1 1 d . . . H6A H 0.7120 0.3186 0.9210 0.071 Uiso 1 1 calc R . . H6B H 0.7268 0.2371 0.8361 0.071 Uiso 1 1 calc R . . O6 O 0.6658(6) 0.1139(5) 0.7501(4) 0.0889(19) Uani 1 1 d . . . N7 N 0.4977(6) 0.4129(4) 1.0060(4) 0.0509(13) Uani 1 1 d . . . C7 C 0.4387(6) 0.3523(4) 0.9196(4) 0.0377(12) Uani 1 1 d . . . O7 O 0.6321(5) 0.4169(4) 1.0185(4) 0.0721(14) Uani 1 1 d . . . C8 C 0.2861(6) 0.3656(4) 0.8990(4) 0.0368(12) Uani 1 1 d . . . N8 N 0.1991(6) 0.4330(4) 0.9481(4) 0.0562(14) Uani 1 1 d . . . H8A H 0.2329 0.4735 0.9970 0.067 Uiso 1 1 calc R . . H8B H 0.1083 0.4366 0.9315 0.067 Uiso 1 1 calc R . . O8 O 0.4171(6) 0.4573(4) 1.0679(4) 0.0787(16) Uani 1 1 d . . . N9 N 0.0739(5) 0.3091(4) 0.7918(4) 0.0477(12) Uani 1 1 d . . . O9 O -0.0105(6) 0.2721(5) 0.8537(6) 0.111(3) Uani 1 1 d . . . O10 O 0.0368(6) 0.3591(9) 0.7179(5) 0.128(3) 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 C0 0.026(3) 0.036(3) 0.049(3) 0.004(2) -0.005(3) -0.002(2) C1 0.056(4) 0.043(3) 0.037(3) 0.001(3) -0.002(3) -0.009(3) N1 0.052(3) 0.043(3) 0.046(3) 0.002(2) -0.005(2) -0.005(2) O1 0.078(3) 0.061(3) 0.067(3) -0.022(3) -0.010(3) -0.010(3) N2 0.042(3) 0.031(2) 0.037(2) -0.0007(19) -0.008(2) -0.003(2) C2 0.040(3) 0.037(3) 0.037(3) -0.004(2) -0.003(2) 0.003(3) O2 0.126(5) 0.099(4) 0.044(3) 0.017(3) -0.016(3) -0.025(4) C3 0.041(3) 0.035(3) 0.037(3) 0.002(2) -0.001(3) -0.003(2) N3 0.049(3) 0.049(3) 0.050(3) -0.005(3) -0.004(3) 0.005(3) O3 0.168(8) 0.144(6) 0.102(5) -0.010(5) 0.052(5) -0.081(6) C4 0.038(3) 0.030(3) 0.035(3) -0.002(2) -0.002(2) -0.003(2) N4 0.071(4) 0.055(3) 0.038(3) -0.004(3) 0.003(3) -0.022(3) O4 0.128(5) 0.053(3) 0.078(3) 0.014(3) -0.004(4) -0.021(3) C5 0.037(3) 0.037(3) 0.036(3) 0.000(2) 0.004(2) 0.006(2) N5 0.047(3) 0.060(3) 0.051(3) -0.005(3) -0.004(3) 0.015(3) O5 0.095(4) 0.186(7) 0.123(5) -0.105(5) -0.051(4) 0.083(5) C6 0.039(3) 0.041(3) 0.040(3) 0.010(3) -0.004(3) -0.007(3) N6 0.033(3) 0.079(4) 0.064(3) -0.008(3) -0.005(3) -0.003(3) O6 0.055(3) 0.111(4) 0.101(4) -0.029(3) -0.007(3) 0.041(3) N7 0.057(3) 0.043(3) 0.053(3) 0.003(3) -0.011(3) -0.013(3) C7 0.044(3) 0.034(3) 0.036(3) 0.002(2) -0.002(3) -0.007(2) O7 0.058(3) 0.093(4) 0.066(3) -0.008(3) -0.014(3) -0.029(3) C8 0.034(3) 0.035(3) 0.041(3) -0.001(2) 0.006(2) -0.003(2) N8 0.049(3) 0.049(3) 0.070(3) -0.022(3) -0.005(3) 0.008(3) O8 0.079(3) 0.090(4) 0.067(3) -0.037(3) -0.014(3) 0.014(3) N9 0.041(3) 0.043(3) 0.060(3) -0.006(3) -0.006(3) 0.005(2) O9 0.037(3) 0.115(5) 0.182(7) 0.081(5) 0.010(4) 0.005(3) O10 0.058(4) 0.241(9) 0.085(4) 0.068(5) -0.019(3) 0.011(5) _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 C0 C4 1.363(7) . ? C0 C8 1.443(8) . ? C0 N9 1.462(7) . ? C1 N1 1.310(7) . ? C1 N2 1.367(7) . ? C1 H1A 0.9300 . ? N1 C2 1.366(7) . ? O1 N3 1.217(6) . ? N2 C3 1.406(7) . ? N2 C4 1.443(7) . ? C2 C3 1.345(7) . ? C2 N3 1.472(7) . ? O2 N3 1.211(7) . ? C3 N4 1.463(7) . ? O3 N4 1.195(8) . ? C4 C5 1.392(7) . ? N4 O4 1.173(7) . ? C5 C6 1.436(8) . ? C5 N5 1.451(7) . ? N5 O5 1.187(7) . ? N5 O6 1.209(7) . ? C6 N6 1.346(7) . ? C6 C7 1.430(8) . ? N6 H6A 0.8600 . ? N6 H6B 0.8600 . ? N7 O8 1.216(7) . ? N7 O7 1.242(7) . ? N7 C7 1.443(7) . ? C7 C8 1.432(8) . ? C8 N8 1.313(7) . ? N8 H8A 0.8600 . ? N8 H8B 0.8600 . ? N9 O10 1.182(8) . ? N9 O9 1.200(7) . ? 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 C4 C0 C8 123.8(5) . . ? C4 C0 N9 118.8(5) . . ? C8 C0 N9 117.4(5) . . ? N1 C1 N2 112.2(5) . . ? N1 C1 H1A 123.9 . . ? N2 C1 H1A 123.9 . . ? C1 N1 C2 105.2(4) . . ? C1 N2 C3 105.7(4) . . ? C1 N2 C4 125.5(4) . . ? C3 N2 C4 128.6(5) . . ? C3 C2 N1 111.9(4) . . ? C3 C2 N3 128.2(5) . . ? N1 C2 N3 119.9(5) . . ? C2 C3 N2 105.0(4) . . ? C2 C3 N4 134.6(5) . . ? N2 C3 N4 120.4(5) . . ? O2 N3 O1 125.1(5) . . ? O2 N3 C2 118.1(5) . . ? O1 N3 C2 116.8(5) . . ? C0 C4 C5 121.0(5) . . ? C0 C4 N2 116.0(5) . . ? C5 C4 N2 122.8(5) . . ? O4 N4 O3 126.4(6) . . ? O4 N4 C3 116.6(5) . . ? O3 N4 C3 116.8(6) . . ? C4 C5 C6 119.0(5) . . ? C4 C5 N5 120.2(5) . . ? C6 C5 N5 120.8(5) . . ? O5 N5 O6 121.2(6) . . ? O5 N5 C5 119.6(5) . . ? O6 N5 C5 119.2(5) . . ? N6 C6 C7 119.9(5) . . ? N6 C6 C5 120.8(6) . . ? C7 C6 C5 119.3(5) . . ? C6 N6 H6A 120.0 . . ? C6 N6 H6B 120.0 . . ? H6A N6 H6B 120.0 . . ? O8 N7 O7 120.0(5) . . ? O8 N7 C7 120.6(5) . . ? O7 N7 C7 119.4(6) . . ? C6 C7 C8 121.5(5) . . ? C6 C7 N7 121.8(5) . . ? C8 C7 N7 116.7(5) . . ? N8 C8 C7 125.1(5) . . ? N8 C8 C0 119.7(5) . . ? C7 C8 C0 115.1(5) . . ? C8 N8 H8A 120.0 . . ? C8 N8 H8B 120.0 . . ? H8A N8 H8B 120.0 . . ? O10 N9 O9 123.1(6) . . ? O10 N9 C0 119.0(6) . . ? O9 N9 C0 117.7(6) . . ? 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 N2 C1 N1 C2 1.7(6) . . . . ? N1 C1 N2 C3 -1.5(6) . . . . ? N1 C1 N2 C4 -176.0(5) . . . . ? C1 N1 C2 C3 -1.2(6) . . . . ? C1 N1 C2 N3 178.8(5) . . . . ? N1 C2 C3 N2 0.3(6) . . . . ? N3 C2 C3 N2 -179.8(5) . . . . ? N1 C2 C3 N4 179.8(6) . . . . ? N3 C2 C3 N4 -0.3(11) . . . . ? C1 N2 C3 C2 0.7(6) . . . . ? C4 N2 C3 C2 174.9(5) . . . . ? C1 N2 C3 N4 -178.9(5) . . . . ? C4 N2 C3 N4 -4.6(9) . . . . ? C3 C2 N3 O2 -10.9(9) . . . . ? N1 C2 N3 O2 169.1(6) . . . . ? C3 C2 N3 O1 169.0(6) . . . . ? N1 C2 N3 O1 -11.0(8) . . . . ? C8 C0 C4 C5 -0.6(8) . . . . ? N9 C0 C4 C5 -179.5(5) . . . . ? C8 C0 C4 N2 176.1(4) . . . . ? N9 C0 C4 N2 -2.7(7) . . . . ? C1 N2 C4 C0 -79.6(7) . . . . ? C3 N2 C4 C0 107.2(6) . . . . ? C1 N2 C4 C5 97.1(7) . . . . ? C3 N2 C4 C5 -76.1(7) . . . . ? C2 C3 N4 O4 150.2(7) . . . . ? N2 C3 N4 O4 -30.3(9) . . . . ? C2 C3 N4 O3 -35.1(11) . . . . ? N2 C3 N4 O3 144.3(7) . . . . ? C0 C4 C5 C6 -1.7(8) . . . . ? N2 C4 C5 C6 -178.2(4) . . . . ? C0 C4 C5 N5 177.7(5) . . . . ? N2 C4 C5 N5 1.2(8) . . . . ? C4 C5 N5 O5 16.5(10) . . . . ? C6 C5 N5 O5 -164.1(7) . . . . ? C4 C5 N5 O6 -165.0(6) . . . . ? C6 C5 N5 O6 14.4(8) . . . . ? C4 C5 C6 N6 -175.0(5) . . . . ? N5 C5 C6 N6 5.6(8) . . . . ? C4 C5 C6 C7 4.4(7) . . . . ? N5 C5 C6 C7 -175.0(5) . . . . ? N6 C6 C7 C8 174.4(5) . . . . ? C5 C6 C7 C8 -5.0(7) . . . . ? N6 C6 C7 N7 -5.5(8) . . . . ? C5 C6 C7 N7 175.1(5) . . . . ? O8 N7 C7 C6 -167.8(5) . . . . ? O7 N7 C7 C6 10.1(8) . . . . ? O8 N7 C7 C8 12.3(7) . . . . ? O7 N7 C7 C8 -169.8(5) . . . . ? C6 C7 C8 N8 -175.5(5) . . . . ? N7 C7 C8 N8 4.4(8) . . . . ? C6 C7 C8 C0 2.7(7) . . . . ? N7 C7 C8 C0 -177.4(4) . . . . ? C4 C0 C8 N8 178.5(5) . . . . ? N9 C0 C8 N8 -2.7(7) . . . . ? C4 C0 C8 C7 0.1(8) . . . . ? N9 C0 C8 C7 179.0(5) . . . . ? C4 C0 N9 O10 -76.9(8) . . . . ? C8 C0 N9 O10 104.2(8) . . . . ? C4 C0 N9 O9 108.7(7) . . . . ? C8 C0 N9 O9 -70.1(7) . . . . ? _diffrn_measured_fraction_theta_max 0.993 _diffrn_reflns_theta_full 25.37 _diffrn_measured_fraction_theta_full 0.993 _refine_diff_density_max 0.288 _refine_diff_density_min -0.241 _refine_diff_density_rms 0.060 _database_code_depnum_ccdc_archive 'CCDC 884546'