# Supplementary Material (ESI) for Chemical Communications # This journal is (c) The Royal Society of Chemistry 2008 data_global _journal_name_full Chem.Commun. _journal_coden_Cambridge 0182 _journal_volume ? _journal_page_first ? _journal_year ? _publ_contact_author_name 'Jiannian Yao' _publ_contact_author_email JNYAO@ICCAS.AC.CN _publ_section_title ; Pyridine-Imide Oligomers ; loop_ _publ_author_name 'Jiannian Yao.' 'Xiao Li.' 'Yaobing Wang.' 'Chuanlang Zhan.' # Attachment 'PIO3.cif' data_sx2094 _database_code_depnum_ccdc_archive 'CCDC 674807' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C32 H25 N7 O10' _chemical_formula_weight 667.59 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 triclinic _symmetry_space_group_name_H-M P-1 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 11.556(2) _cell_length_b 12.222(2) _cell_length_c 12.249(2) _cell_angle_alpha 67.75(3) _cell_angle_beta 82.17(3) _cell_angle_gamma 88.75(3) _cell_volume 1585.4(5) _cell_formula_units_Z 2 _cell_measurement_temperature 296(2) _cell_measurement_reflns_used 9000 _cell_measurement_theta_min 2.01 _cell_measurement_theta_max 25.00 _exptl_crystal_description plate _exptl_crystal_colour colorless _exptl_crystal_size_max 0.25 _exptl_crystal_size_mid 0.23 _exptl_crystal_size_min 0.09 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.398 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 692 _exptl_absorpt_coefficient_mu 0.107 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.9738 _exptl_absorpt_correction_T_max 0.9905 _exptl_absorpt_process_details 'ABSCOR by T.Higashi 8 March, 1995' _exptl_special_details ; ? ; _diffrn_ambient_temperature 296(2) _diffrn_radiation_wavelength 0.71069 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'rotating anode' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Rigaku raxis Rapid IP Area Detector' _diffrn_measurement_method '\w scans at fixed \c = 45\%' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 9000 _diffrn_reflns_av_R_equivalents 0.0698 _diffrn_reflns_av_sigmaI/netI 0.0893 _diffrn_reflns_limit_h_min -13 _diffrn_reflns_limit_h_max 13 _diffrn_reflns_limit_k_min -14 _diffrn_reflns_limit_k_max 14 _diffrn_reflns_limit_l_min -14 _diffrn_reflns_limit_l_max 14 _diffrn_reflns_theta_min 2.01 _diffrn_reflns_theta_max 25.00 _reflns_number_total 5510 _reflns_number_gt 3011 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Rapid Auto(Rigaku 2001)' _computing_cell_refinement 'Rapid Auto(Rigaku 2001)' _computing_data_reduction 'Rapid Auto(Rigaku 2001)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'XP in Siemens SHELXTL (Sheldrick, 1994)' _computing_publication_material 'SHELX97 (Sheldrick, 1997)' _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. Because one of the carbon atoms, C1, is disordered in two orientations, we used a disordered model, in which C1 was divided into two parts, C1 and C1'. Therefore, 2 restraints (SADI) were used to make the two disordered parts have similar bond length and bond angle; 6 restraints (SIMU) were used to make C1 and C1' have similar anisotropic displacement parameters; 12 restraints (ISOR) were used to make C1 and C1' have approximately isotropic displacement parameters. Totally, 20 restraints were used to describe the disordered model. ; _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^)+(0.0541P)^2^+1.2191P] 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 5510 _refine_ls_number_parameters 452 _refine_ls_number_restraints 20 _refine_ls_R_factor_all 0.1767 _refine_ls_R_factor_gt 0.0984 _refine_ls_wR_factor_ref 0.2075 _refine_ls_wR_factor_gt 0.1789 _refine_ls_goodness_of_fit_ref 1.150 _refine_ls_restrained_S_all 1.150 _refine_ls_shift/su_max 0.002 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group O1 O 0.9803(4) 0.2343(4) 0.4337(4) 0.0984(14) Uani 1 1 d D A . O2 O 1.0121(5) 0.3460(7) 0.5308(7) 0.178(3) Uani 1 1 d . A . O3 O 0.4469(3) 0.2131(4) 0.4677(4) 0.0926(14) Uani 1 1 d . A . O4 O 0.4682(3) 0.0444(3) 0.3540(4) 0.0813(12) Uani 1 1 d . A . O5 O 1.0463(3) 0.1187(3) 0.0745(4) 0.0811(12) Uani 1 1 d . A . O6 O 1.1222(3) 0.3393(3) 0.0775(4) 0.0739(11) Uani 1 1 d . A . O7 O 0.6256(3) 0.5896(3) 0.2688(3) 0.0740(11) Uani 1 1 d . A . O8 O 0.4311(3) 0.4804(3) 0.2176(4) 0.0758(11) Uani 1 1 d . A . O9 O 0.7818(3) 0.2583(4) -0.0549(4) 0.0758(12) Uani 1 1 d . A . O10 O 0.6696(3) 0.1466(3) -0.1067(4) 0.0721(11) Uani 1 1 d . A . N1 N 0.7468(4) 0.2643(3) 0.4679(4) 0.0578(11) Uani 1 1 d . . . N2 N 0.6126(3) 0.1520(3) 0.3838(4) 0.0590(11) Uani 1 1 d . A . H2A H 0.6871 0.1642 0.3696 0.071 Uiso 1 1 calc R . . N3 N 0.7642(3) 0.0961(3) 0.2342(3) 0.0490(10) Uani 1 1 d . . . N4 N 0.9426(3) 0.2457(3) 0.1437(4) 0.0531(11) Uani 1 1 d . A . H4A H 0.8737 0.2540 0.1758 0.064 Uiso 1 1 calc R . . N5 N 0.8553(3) 0.4359(3) 0.1774(3) 0.0437(9) Uani 1 1 d . . . N6 N 0.6265(3) 0.4495(3) 0.1871(4) 0.0525(10) Uani 1 1 d . A . H6A H 0.6739 0.4056 0.1629 0.063 Uiso 1 1 calc R . . N7 N 0.5899(3) 0.3199(3) 0.0643(4) 0.0472(10) Uani 1 1 d . . . C1 C 1.141(3) 0.125(3) 0.385(4) 0.142(15) Uani 0.28(2) 1 d PDU A 1 H1B H 1.2246 0.1240 0.3720 0.212 Uiso 0.28(2) 1 calc PR A 1 H1C H 1.1111 0.1334 0.3125 0.212 Uiso 0.28(2) 1 calc PR A 1 H1D H 1.1106 0.0524 0.4470 0.212 Uiso 0.28(2) 1 calc PR A 1 C1' C 1.1382(11) 0.1118(12) 0.4991(16) 0.155(7) Uani 0.72(2) 1 d PDU A 2 H1'A H 1.2211 0.1030 0.4858 0.232 Uiso 0.72(2) 1 calc PR A 2 H1'B H 1.0983 0.0466 0.4933 0.232 Uiso 0.72(2) 1 calc PR A 2 H1'C H 1.1165 0.1133 0.5770 0.232 Uiso 0.72(2) 1 calc PR A 2 C2 C 1.1081(7) 0.2152(9) 0.4153(11) 0.147(4) Uani 1 1 d D . . H2B H 1.1445 0.2864 0.3547 0.177 Uiso 1 1 d R A 3 H2C H 1.1383 0.2060 0.4894 0.177 Uiso 1 1 d R A 3 C3 C 0.9461(7) 0.3036(6) 0.4926(7) 0.096(2) Uani 1 1 d . . . C4 C 0.8171(5) 0.3224(5) 0.5052(5) 0.0678(15) Uani 1 1 d . A . C5 C 0.7769(7) 0.3994(6) 0.5598(6) 0.098(2) Uani 1 1 d . . . H5B H 0.8292 0.4411 0.5821 0.117 Uiso 1 1 calc R A . C6 C 0.6594(8) 0.4133(6) 0.5803(6) 0.100(2) Uani 1 1 d . A . H6B H 0.6306 0.4639 0.6175 0.120 Uiso 1 1 calc R . . C7 C 0.5848(6) 0.3516(5) 0.5453(5) 0.0800(18) Uani 1 1 d . . . H7B H 0.5043 0.3577 0.5599 0.096 Uiso 1 1 calc R A . C8 C 0.6324(5) 0.2796(4) 0.4875(4) 0.0598(14) Uani 1 1 d . A . C9 C 0.5515(5) 0.2124(5) 0.4475(5) 0.0626(15) Uani 1 1 d . . . C10 C 0.5694(5) 0.0747(4) 0.3400(5) 0.0592(14) Uani 1 1 d . . . C11 C 0.6639(5) 0.0324(4) 0.2699(5) 0.0556(13) Uani 1 1 d . A . C12 C 0.6465(5) -0.0658(5) 0.2439(5) 0.0704(16) Uani 1 1 d . . . H12A H 0.5749 -0.1071 0.2678 0.085 Uiso 1 1 calc R A . C13 C 0.7369(6) -0.1009(5) 0.1826(6) 0.0771(18) Uani 1 1 d . A . H13A H 0.7280 -0.1684 0.1664 0.092 Uiso 1 1 calc R . . C14 C 0.8409(5) -0.0374(5) 0.1444(5) 0.0669(15) Uani 1 1 d . . . H14A H 0.9033 -0.0614 0.1032 0.080 Uiso 1 1 calc R A . C15 C 0.8505(4) 0.0629(4) 0.1688(4) 0.0520(12) Uani 1 1 d . A . C16 C 0.9584(4) 0.1431(4) 0.1230(4) 0.0537(13) Uani 1 1 d . . . C17 C 1.0213(4) 0.3367(4) 0.1203(4) 0.0495(12) Uani 1 1 d . . . C18 C 0.9723(4) 0.4344(4) 0.1562(4) 0.0495(12) Uani 1 1 d . A . C19 C 1.0440(5) 0.5157(5) 0.1695(5) 0.0661(15) Uani 1 1 d . . . H19A H 1.1246 0.5151 0.1509 0.079 Uiso 1 1 calc R A . C20 C 0.9937(5) 0.5974(5) 0.2108(5) 0.0729(17) Uani 1 1 d . A . H20A H 1.0404 0.6521 0.2223 0.087 Uiso 1 1 calc R . . C21 C 0.8747(5) 0.5989(4) 0.2354(5) 0.0646(15) Uani 1 1 d . . . H21A H 0.8394 0.6523 0.2659 0.077 Uiso 1 1 calc R A . C22 C 0.8086(4) 0.5184(4) 0.2134(4) 0.0477(12) Uani 1 1 d . A . C23 C 0.6773(4) 0.5239(4) 0.2280(4) 0.0518(13) Uani 1 1 d . . . C24 C 0.5107(4) 0.4346(4) 0.1792(5) 0.0553(13) Uani 1 1 d . . . C25 C 0.4935(4) 0.3555(4) 0.1140(4) 0.0467(12) Uani 1 1 d . A . C26 C 0.3825(4) 0.3265(5) 0.1035(5) 0.0609(14) Uani 1 1 d . . . H26A H 0.3176 0.3544 0.1376 0.073 Uiso 1 1 calc R A . C27 C 0.3695(4) 0.2553(5) 0.0415(5) 0.0668(15) Uani 1 1 d . A . H27A H 0.2954 0.2325 0.0349 0.080 Uiso 1 1 calc R . . C28 C 0.4672(4) 0.2184(4) -0.0105(5) 0.0590(14) Uani 1 1 d . . . H28A H 0.4605 0.1712 -0.0538 0.071 Uiso 1 1 calc R A . C29 C 0.5756(4) 0.2528(4) 0.0030(4) 0.0469(12) Uani 1 1 d . A . C30 C 0.6878(4) 0.2213(4) -0.0549(4) 0.0525(13) Uani 1 1 d . . . C31 C 0.7718(5) 0.1137(6) -0.1686(6) 0.092(2) Uani 1 1 d . . . H31A H 0.8168 0.1841 -0.2222 0.110 Uiso 1 1 calc R A . H31B H 0.8210 0.0652 -0.1117 0.110 Uiso 1 1 calc R . . C32 C 0.7346(6) 0.0486(6) -0.2353(6) 0.100(2) Uani 1 1 d . A . H32A H 0.8019 0.0264 -0.2766 0.150 Uiso 1 1 calc R . . H32B H 0.6866 0.0974 -0.2920 0.150 Uiso 1 1 calc R . . H32C H 0.6905 -0.0212 -0.1817 0.150 Uiso 1 1 calc R . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 O1 0.079(3) 0.119(4) 0.117(4) -0.064(3) -0.021(3) 0.017(3) O2 0.122(5) 0.234(7) 0.265(9) -0.181(7) -0.066(5) 0.013(5) O3 0.061(3) 0.110(3) 0.108(4) -0.051(3) 0.013(2) 0.013(2) O4 0.059(2) 0.089(3) 0.098(3) -0.041(3) 0.002(2) -0.016(2) O5 0.064(2) 0.090(3) 0.106(3) -0.063(3) 0.009(2) 0.019(2) O6 0.0317(18) 0.091(3) 0.104(3) -0.047(3) 0.0024(19) -0.0001(18) O7 0.074(2) 0.074(2) 0.094(3) -0.057(2) -0.003(2) 0.016(2) O8 0.051(2) 0.099(3) 0.096(3) -0.060(3) -0.008(2) 0.024(2) O9 0.042(2) 0.108(3) 0.098(3) -0.064(3) -0.002(2) -0.008(2) O10 0.051(2) 0.089(3) 0.104(3) -0.067(3) -0.012(2) 0.0055(19) N1 0.070(3) 0.057(3) 0.045(3) -0.021(2) 0.000(2) 0.004(2) N2 0.052(2) 0.057(3) 0.068(3) -0.029(2) 0.012(2) -0.008(2) N3 0.057(2) 0.046(2) 0.050(3) -0.027(2) -0.004(2) 0.002(2) N4 0.038(2) 0.058(2) 0.070(3) -0.038(2) 0.007(2) -0.0025(19) N5 0.043(2) 0.038(2) 0.050(3) -0.017(2) -0.0042(18) -0.0041(17) N6 0.049(2) 0.057(2) 0.062(3) -0.036(2) -0.005(2) 0.0097(19) N7 0.038(2) 0.046(2) 0.054(3) -0.017(2) -0.0028(19) 0.0018(18) C1 0.14(2) 0.15(2) 0.15(2) -0.074(16) -0.005(15) 0.027(15) C1' 0.133(10) 0.146(11) 0.151(14) -0.010(9) -0.044(9) 0.012(8) C2 0.094(6) 0.160(9) 0.166(10) -0.030(8) -0.039(6) 0.031(6) C3 0.097(5) 0.099(5) 0.104(6) -0.050(5) -0.027(4) -0.004(4) C4 0.091(4) 0.061(3) 0.055(4) -0.026(3) -0.013(3) 0.003(3) C5 0.146(7) 0.086(5) 0.086(5) -0.054(4) -0.037(5) 0.024(5) C6 0.150(7) 0.092(5) 0.080(5) -0.056(4) -0.028(5) 0.046(5) C7 0.099(5) 0.089(4) 0.061(4) -0.040(4) -0.012(4) 0.028(4) C8 0.080(4) 0.053(3) 0.043(3) -0.017(3) 0.000(3) 0.013(3) C9 0.066(4) 0.061(3) 0.048(3) -0.013(3) 0.010(3) 0.008(3) C10 0.061(3) 0.050(3) 0.060(4) -0.016(3) 0.000(3) -0.011(3) C11 0.066(3) 0.049(3) 0.051(3) -0.018(3) -0.008(3) -0.007(3) C12 0.085(4) 0.054(3) 0.078(4) -0.030(3) -0.014(3) -0.008(3) C13 0.109(5) 0.046(3) 0.091(5) -0.040(3) -0.022(4) 0.000(3) C14 0.086(4) 0.057(3) 0.067(4) -0.035(3) -0.010(3) 0.013(3) C15 0.063(3) 0.044(3) 0.052(3) -0.023(3) -0.008(3) 0.009(2) C16 0.059(3) 0.057(3) 0.053(3) -0.032(3) -0.005(3) 0.014(3) C17 0.038(3) 0.062(3) 0.050(3) -0.023(3) -0.006(2) 0.004(2) C18 0.043(3) 0.053(3) 0.052(3) -0.020(3) -0.006(2) -0.009(2) C19 0.054(3) 0.067(3) 0.075(4) -0.024(3) -0.005(3) -0.016(3) C20 0.083(4) 0.064(4) 0.087(5) -0.043(4) -0.017(3) -0.020(3) C21 0.072(4) 0.053(3) 0.076(4) -0.032(3) -0.010(3) -0.004(3) C22 0.058(3) 0.042(3) 0.045(3) -0.018(2) -0.004(2) -0.004(2) C23 0.059(3) 0.048(3) 0.053(3) -0.025(3) -0.007(3) 0.007(2) C24 0.043(3) 0.064(3) 0.060(4) -0.026(3) -0.006(3) 0.015(3) C25 0.042(3) 0.049(3) 0.047(3) -0.015(3) -0.009(2) 0.009(2) C26 0.036(3) 0.075(4) 0.080(4) -0.040(3) -0.007(3) 0.009(2) C27 0.041(3) 0.076(4) 0.085(4) -0.031(4) -0.014(3) 0.001(3) C28 0.045(3) 0.067(3) 0.072(4) -0.031(3) -0.014(3) -0.005(3) C29 0.046(3) 0.047(3) 0.049(3) -0.020(3) -0.007(2) 0.002(2) C30 0.047(3) 0.062(3) 0.053(3) -0.026(3) -0.009(2) 0.002(2) C31 0.071(4) 0.121(5) 0.113(6) -0.081(5) -0.009(4) 0.021(4) C32 0.125(6) 0.089(5) 0.098(6) -0.052(4) -0.002(5) 0.000(4) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag O1 C3 1.328(8) . ? O1 C2 1.490(8) . ? O2 C3 1.169(8) . ? O3 C9 1.201(6) . ? O4 C10 1.204(6) . ? O5 C16 1.195(5) . ? O6 C17 1.207(5) . ? O7 C23 1.206(5) . ? O8 C24 1.200(5) . ? O9 C30 1.186(5) . ? O10 C30 1.329(5) . ? O10 C31 1.448(6) . ? N1 C4 1.320(6) . ? N1 C8 1.333(6) . ? N2 C10 1.381(6) . ? N2 C9 1.384(6) . ? N2 H2A 0.8600 . ? N3 C11 1.336(6) . ? N3 C15 1.346(6) . ? N4 C17 1.371(6) . ? N4 C16 1.375(5) . ? N4 H4A 0.8600 . ? N5 C22 1.324(5) . ? N5 C18 1.342(5) . ? N6 C23 1.367(6) . ? N6 C24 1.376(6) . ? N6 H6A 0.8600 . ? N7 C29 1.330(6) . ? N7 C25 1.340(5) . ? C1 C2 1.325(17) . ? C1 H1B 0.9600 . ? C1 H1C 0.9600 . ? C1 H1D 0.9600 . ? C1' C2 1.367(12) . ? C1' H1'A 0.9600 . ? C1' H1'B 0.9600 . ? C1' H1'C 0.9600 . ? C1' H2C 1.1110 . ? C2 H2B 0.9624 . ? C2 H2C 0.9833 . ? C3 C4 1.499(9) . ? C4 C5 1.387(8) . ? C5 C6 1.365(9) . ? C5 H5B 0.9300 . ? C6 C7 1.367(9) . ? C6 H6B 0.9300 . ? C7 C8 1.387(7) . ? C7 H7B 0.9300 . ? C8 C9 1.500(7) . ? C10 C11 1.501(7) . ? C11 C12 1.378(7) . ? C12 C13 1.360(8) . ? C12 H12A 0.9300 . ? C13 C14 1.370(7) . ? C13 H13A 0.9300 . ? C14 C15 1.377(6) . ? C14 H14A 0.9300 . ? C15 C16 1.508(7) . ? C17 C18 1.498(6) . ? C18 C19 1.377(6) . ? C19 C20 1.366(7) . ? C19 H19A 0.9300 . ? C20 C21 1.368(7) . ? C20 H20A 0.9300 . ? C21 C22 1.383(6) . ? C21 H21A 0.9300 . ? C22 C23 1.506(6) . ? C24 C25 1.499(7) . ? C25 C26 1.373(6) . ? C26 C27 1.376(7) . ? C26 H26A 0.9300 . ? C27 C28 1.373(7) . ? C27 H27A 0.9300 . ? C28 C29 1.381(6) . ? C28 H28A 0.9300 . ? C29 C30 1.506(6) . ? C31 C32 1.446(8) . ? C31 H31A 0.9700 . ? C31 H31B 0.9700 . ? C32 H32A 0.9600 . ? C32 H32B 0.9600 . ? C32 H32C 0.9600 . ? 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 C3 O1 C2 116.8(6) . . ? C30 O10 C31 116.4(4) . . ? C4 N1 C8 117.4(4) . . ? C10 N2 C9 128.4(4) . . ? C10 N2 H2A 115.8 . . ? C9 N2 H2A 115.8 . . ? C11 N3 C15 118.0(4) . . ? C17 N4 C16 128.9(4) . . ? C17 N4 H4A 115.5 . . ? C16 N4 H4A 115.5 . . ? C22 N5 C18 118.0(4) . . ? C23 N6 C24 129.5(4) . . ? C23 N6 H6A 115.3 . . ? C24 N6 H6A 115.3 . . ? C29 N7 C25 117.5(4) . . ? C2 C1 H1B 109.5 . . ? C2 C1 H1C 109.5 . . ? H1B C1 H1C 109.5 . . ? C2 C1 H1D 109.5 . . ? H1B C1 H1D 109.5 . . ? H1C C1 H1D 109.5 . . ? C2 C1' H1'A 109.5 . . ? C2 C1' H1'B 109.5 . . ? H1'A C1' H1'B 109.5 . . ? C2 C1' H1'C 109.5 . . ? H1'A C1' H1'C 109.5 . . ? H1'B C1' H1'C 109.5 . . ? C2 C1' H2C 45.3 . . ? H1'A C1' H2C 98.7 . . ? H1'B C1' H2C 148.4 . . ? H1'C C1' H2C 72.5 . . ? C1 C2 C1' 60.0(18) . . ? C1 C2 O1 117.3(16) . . ? C1' C2 O1 111.6(9) . . ? C1 C2 H2B 108.1 . . ? C1' C2 H2B 139.6 . . ? O1 C2 H2B 107.9 . . ? C1 C2 H2C 109.1 . . ? C1' C2 H2C 53.4 . . ? O1 C2 H2C 107.2 . . ? H2B C2 H2C 106.7 . . ? O2 C3 O1 122.1(7) . . ? O2 C3 C4 123.5(7) . . ? O1 C3 C4 114.4(6) . . ? N1 C4 C5 122.8(6) . . ? N1 C4 C3 120.1(5) . . ? C5 C4 C3 117.1(6) . . ? C6 C5 C4 119.1(7) . . ? C6 C5 H5B 120.4 . . ? C4 C5 H5B 120.4 . . ? C5 C6 C7 119.0(6) . . ? C5 C6 H6B 120.5 . . ? C7 C6 H6B 120.5 . . ? C6 C7 C8 118.2(6) . . ? C6 C7 H7B 120.9 . . ? C8 C7 H7B 120.9 . . ? N1 C8 C7 123.4(5) . . ? N1 C8 C9 117.8(4) . . ? C7 C8 C9 118.7(5) . . ? O3 C9 N2 125.0(5) . . ? O3 C9 C8 123.5(5) . . ? N2 C9 C8 111.6(4) . . ? O4 C10 N2 125.1(5) . . ? O4 C10 C11 122.8(5) . . ? N2 C10 C11 112.0(4) . . ? N3 C11 C12 122.7(5) . . ? N3 C11 C10 115.9(4) . . ? C12 C11 C10 121.4(5) . . ? C13 C12 C11 118.2(5) . . ? C13 C12 H12A 120.9 . . ? C11 C12 H12A 120.9 . . ? C12 C13 C14 120.5(5) . . ? C12 C13 H13A 119.7 . . ? C14 C13 H13A 119.7 . . ? C13 C14 C15 118.2(5) . . ? C13 C14 H14A 120.9 . . ? C15 C14 H14A 120.9 . . ? N3 C15 C14 122.2(5) . . ? N3 C15 C16 115.8(4) . . ? C14 C15 C16 122.0(5) . . ? O5 C16 N4 125.0(5) . . ? O5 C16 C15 123.2(4) . . ? N4 C16 C15 111.9(4) . . ? O6 C17 N4 124.7(4) . . ? O6 C17 C18 121.5(4) . . ? N4 C17 C18 113.8(4) . . ? N5 C18 C19 122.4(4) . . ? N5 C18 C17 116.1(4) . . ? C19 C18 C17 121.4(4) . . ? C20 C19 C18 118.4(5) . . ? C20 C19 H19A 120.8 . . ? C18 C19 H19A 120.8 . . ? C19 C20 C21 120.1(5) . . ? C19 C20 H20A 119.9 . . ? C21 C20 H20A 119.9 . . ? C20 C21 C22 117.9(5) . . ? C20 C21 H21A 121.0 . . ? C22 C21 H21A 121.0 . . ? N5 C22 C21 123.0(4) . . ? N5 C22 C23 117.0(4) . . ? C21 C22 C23 120.0(4) . . ? O7 C23 N6 125.2(4) . . ? O7 C23 C22 122.3(4) . . ? N6 C23 C22 112.4(4) . . ? O8 C24 N6 124.9(5) . . ? O8 C24 C25 122.6(4) . . ? N6 C24 C25 112.5(4) . . ? N7 C25 C26 123.1(4) . . ? N7 C25 C24 117.0(4) . . ? C26 C25 C24 119.8(4) . . ? C25 C26 C27 118.5(5) . . ? C25 C26 H26A 120.7 . . ? C27 C26 H26A 120.7 . . ? C28 C27 C26 119.3(5) . . ? C28 C27 H27A 120.4 . . ? C26 C27 H27A 120.4 . . ? C27 C28 C29 118.5(5) . . ? C27 C28 H28A 120.8 . . ? C29 C28 H28A 120.8 . . ? N7 C29 C28 123.1(4) . . ? N7 C29 C30 114.4(4) . . ? C28 C29 C30 122.5(4) . . ? O9 C30 O10 123.4(4) . . ? O9 C30 C29 124.5(4) . . ? O10 C30 C29 112.1(4) . . ? C32 C31 O10 108.9(5) . . ? C32 C31 H31A 109.9 . . ? O10 C31 H31A 109.9 . . ? C32 C31 H31B 109.9 . . ? O10 C31 H31B 109.9 . . ? H31A C31 H31B 108.3 . . ? C31 C32 H32A 109.5 . . ? C31 C32 H32B 109.5 . . ? H32A C32 H32B 109.5 . . ? C31 C32 H32C 109.5 . . ? H32A C32 H32C 109.5 . . ? H32B C32 H32C 109.5 . . ? 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 C3 O1 C2 C1 163(3) . . . . ? C3 O1 C2 C1' 97.1(13) . . . . ? C2 O1 C3 O2 -1.5(12) . . . . ? C2 O1 C3 C4 178.3(6) . . . . ? C8 N1 C4 C5 -1.8(8) . . . . ? C8 N1 C4 C3 176.3(5) . . . . ? O2 C3 C4 N1 -174.7(8) . . . . ? O1 C3 C4 N1 5.5(9) . . . . ? O2 C3 C4 C5 3.5(12) . . . . ? O1 C3 C4 C5 -176.3(6) . . . . ? N1 C4 C5 C6 2.5(10) . . . . ? C3 C4 C5 C6 -175.7(6) . . . . ? C4 C5 C6 C7 -0.7(11) . . . . ? C5 C6 C7 C8 -1.6(10) . . . . ? C4 N1 C8 C7 -0.7(8) . . . . ? C4 N1 C8 C9 -178.9(5) . . . . ? C6 C7 C8 N1 2.4(9) . . . . ? C6 C7 C8 C9 -179.4(5) . . . . ? C10 N2 C9 O3 -5.9(9) . . . . ? C10 N2 C9 C8 175.1(5) . . . . ? N1 C8 C9 O3 174.8(5) . . . . ? C7 C8 C9 O3 -3.5(8) . . . . ? N1 C8 C9 N2 -6.2(7) . . . . ? C7 C8 C9 N2 175.5(5) . . . . ? C9 N2 C10 O4 -2.2(9) . . . . ? C9 N2 C10 C11 177.0(5) . . . . ? C15 N3 C11 C12 1.1(8) . . . . ? C15 N3 C11 C10 -178.5(4) . . . . ? O4 C10 C11 N3 162.3(5) . . . . ? N2 C10 C11 N3 -16.9(7) . . . . ? O4 C10 C11 C12 -17.3(8) . . . . ? N2 C10 C11 C12 163.5(5) . . . . ? N3 C11 C12 C13 2.0(9) . . . . ? C10 C11 C12 C13 -178.4(5) . . . . ? C11 C12 C13 C14 -2.1(9) . . . . ? C12 C13 C14 C15 -0.7(9) . . . . ? C11 N3 C15 C14 -4.1(7) . . . . ? C11 N3 C15 C16 175.5(4) . . . . ? C13 C14 C15 N3 4.0(8) . . . . ? C13 C14 C15 C16 -175.6(5) . . . . ? C17 N4 C16 O5 -3.4(9) . . . . ? C17 N4 C16 C15 176.7(5) . . . . ? N3 C15 C16 O5 171.9(5) . . . . ? C14 C15 C16 O5 -8.5(8) . . . . ? N3 C15 C16 N4 -8.1(6) . . . . ? C14 C15 C16 N4 171.5(5) . . . . ? C16 N4 C17 O6 -1.3(8) . . . . ? C16 N4 C17 C18 -179.6(5) . . . . ? C22 N5 C18 C19 -0.6(7) . . . . ? C22 N5 C18 C17 177.7(4) . . . . ? O6 C17 C18 N5 165.6(5) . . . . ? N4 C17 C18 N5 -16.1(6) . . . . ? O6 C17 C18 C19 -16.0(8) . . . . ? N4 C17 C18 C19 162.3(5) . . . . ? N5 C18 C19 C20 2.9(8) . . . . ? C17 C18 C19 C20 -175.3(5) . . . . ? C18 C19 C20 C21 -1.4(9) . . . . ? C19 C20 C21 C22 -2.1(9) . . . . ? C18 N5 C22 C21 -3.2(7) . . . . ? C18 N5 C22 C23 175.7(4) . . . . ? C20 C21 C22 N5 4.6(8) . . . . ? C20 C21 C22 C23 -174.3(5) . . . . ? C24 N6 C23 O7 2.3(9) . . . . ? C24 N6 C23 C22 -176.0(5) . . . . ? N5 C22 C23 O7 174.3(5) . . . . ? C21 C22 C23 O7 -6.8(8) . . . . ? N5 C22 C23 N6 -7.4(6) . . . . ? C21 C22 C23 N6 171.5(5) . . . . ? C23 N6 C24 O8 -6.5(9) . . . . ? C23 N6 C24 C25 172.3(5) . . . . ? C29 N7 C25 C26 -0.4(7) . . . . ? C29 N7 C25 C24 -177.9(4) . . . . ? O8 C24 C25 N7 173.1(5) . . . . ? N6 C24 C25 N7 -5.8(6) . . . . ? O8 C24 C25 C26 -4.5(8) . . . . ? N6 C24 C25 C26 176.6(5) . . . . ? N7 C25 C26 C27 1.5(8) . . . . ? C24 C25 C26 C27 179.0(5) . . . . ? C25 C26 C27 C28 -1.8(8) . . . . ? C26 C27 C28 C29 1.0(8) . . . . ? C25 N7 C29 C28 -0.5(7) . . . . ? C25 N7 C29 C30 177.2(4) . . . . ? C27 C28 C29 N7 0.2(8) . . . . ? C27 C28 C29 C30 -177.3(5) . . . . ? C31 O10 C30 O9 -1.9(8) . . . . ? C31 O10 C30 C29 178.0(5) . . . . ? N7 C29 C30 O9 -5.2(7) . . . . ? C28 C29 C30 O9 172.5(5) . . . . ? N7 C29 C30 O10 174.9(4) . . . . ? C28 C29 C30 O10 -7.4(7) . . . . ? C30 O10 C31 C32 -170.7(5) . . . . ? _diffrn_measured_fraction_theta_max 0.986 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 0.986 _refine_diff_density_max 0.233 _refine_diff_density_min -0.237 _refine_diff_density_rms 0.048 # Attachment 'PIO2.cif' data_shelxl _database_code_depnum_ccdc_archive 'CCDC 674808' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C25 H21 N5 O8' _chemical_formula_sum 'C25 H21 N5 O8' _chemical_formula_weight 519.47 _chemical_absolute_configuration unk 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 'P 21 21 21' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' 'x+1/2, -y+1/2, -z' '-x, y+1/2, -z+1/2' '-x+1/2, -y, z+1/2' _cell_length_a 7.7201(14) _cell_length_b 8.3506(15) _cell_length_c 37.025(7) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 2386.9(7) _cell_formula_units_Z 4 _cell_measurement_temperature 113(2) _cell_measurement_reflns_used 5605 _cell_measurement_theta_min 2.4 _cell_measurement_theta_max 27.9 _exptl_crystal_description prism _exptl_crystal_colour colorless _exptl_crystal_size_max 0.20 _exptl_crystal_size_mid 0.20 _exptl_crystal_size_min 0.20 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.446 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1080 _exptl_absorpt_coefficient_mu 0.110 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.9783 _exptl_absorpt_correction_T_max 0.9783 _exptl_absorpt_process_details 'Jacobson, R. (1998) Private communication' _exptl_special_details ; ? ; _diffrn_ambient_temperature 113(2) _diffrn_radiation_wavelength 0.71070 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'rotating anode' _diffrn_radiation_monochromator confocal _diffrn_measurement_device_type 'Rigaku Saturn' _diffrn_measurement_method \w _diffrn_detector_area_resol_mean 7.31 _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 21235 _diffrn_reflns_av_R_equivalents 0.0319 _diffrn_reflns_av_sigmaI/netI 0.0203 _diffrn_reflns_limit_h_min -10 _diffrn_reflns_limit_h_max 9 _diffrn_reflns_limit_k_min -10 _diffrn_reflns_limit_k_max 10 _diffrn_reflns_limit_l_min -48 _diffrn_reflns_limit_l_max 48 _diffrn_reflns_theta_min 2.50 _diffrn_reflns_theta_max 27.87 _reflns_number_total 3244 _reflns_number_gt 3134 _reflns_threshold_expression >2sigma(I) _computing_data_collection CrystalClear _computing_cell_refinement CrystalClear _computing_data_reduction CrystalClear _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics ? _computing_publication_material 'CrystalStructure 3.7.0' _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^)+(0.0401P)^2^+0.4487P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment mixed _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_abs_structure_details 'None, Friedel Pairs merged' _refine_ls_abs_structure_Flack ? _refine_ls_number_reflns 3244 _refine_ls_number_parameters 354 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0327 _refine_ls_R_factor_gt 0.0312 _refine_ls_wR_factor_ref 0.0750 _refine_ls_wR_factor_gt 0.0738 _refine_ls_goodness_of_fit_ref 1.037 _refine_ls_restrained_S_all 1.037 _refine_ls_shift/su_max 0.001 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group O1 O 0.92206(18) -0.12927(16) 0.92875(3) 0.0319(3) Uani 1 1 d . . . O2 O 0.69883(16) -0.30352(16) 0.92689(3) 0.0286(3) Uani 1 1 d . . . O3 O 1.07311(18) -0.03888(15) 0.76616(3) 0.0317(3) Uani 1 1 d . . . O4 O 1.23248(17) 0.26482(17) 0.78158(3) 0.0318(3) Uani 1 1 d . . . O5 O 1.01897(17) 0.45990(16) 0.96021(3) 0.0327(3) Uani 1 1 d . . . O6 O 0.72500(18) 0.28126(19) 0.98007(3) 0.0402(4) Uani 1 1 d . . . O7 O 0.41043(19) -0.11837(16) 0.82786(3) 0.0350(3) Uani 1 1 d . . . O8 O 0.58269(16) 0.09617(15) 0.82103(3) 0.0255(3) Uani 1 1 d . . . N1 N 0.92618(18) -0.13640(17) 0.85389(3) 0.0218(3) Uani 1 1 d . . . N2 N 1.0676(2) 0.10557(18) 0.81900(4) 0.0262(3) Uani 1 1 d . . . H2A H 1.035(3) 0.099(3) 0.8419(6) 0.048(7) Uiso 1 1 d . . . N3 N 1.09331(17) 0.31803(16) 0.87161(3) 0.0212(3) Uani 1 1 d . . . N4 N 0.86928(19) 0.27604(18) 0.92590(4) 0.0257(3) Uani 1 1 d . . . H4A H 0.867(2) 0.234(2) 0.9040(5) 0.021(5) Uiso 1 1 d . . . N5 N 0.60399(17) 0.11975(17) 0.89527(3) 0.0222(3) Uani 1 1 d . . . C1 C 0.8445(2) -0.2509(2) 0.87247(4) 0.0219(3) Uani 1 1 d . . . C2 C 0.7857(2) -0.3923(2) 0.85689(4) 0.0254(3) Uani 1 1 d . . . H2 H 0.7273 -0.4705 0.8710 0.031 Uiso 1 1 calc R . . C3 C 0.8143(2) -0.4168(2) 0.82014(4) 0.0279(4) Uani 1 1 d . . . H3 H 0.7775 -0.5130 0.8088 0.033 Uiso 1 1 calc R . . C4 C 0.8974(2) -0.2985(2) 0.80043(4) 0.0264(3) Uani 1 1 d . . . H4 H 0.9182 -0.3113 0.7753 0.032 Uiso 1 1 calc R . . C5 C 0.9494(2) -0.1609(2) 0.81836(4) 0.0228(3) Uani 1 1 d . . . C6 C 0.8282(2) -0.2190(2) 0.91244(4) 0.0232(3) Uani 1 1 d . . . C7 C 1.0368(2) -0.0285(2) 0.79778(4) 0.0250(3) Uani 1 1 d . . . C8 C 1.1659(2) 0.2375(2) 0.81060(4) 0.0245(3) Uani 1 1 d . . . C9 C 1.1902(2) 0.3481(2) 0.84238(4) 0.0232(3) Uani 1 1 d . . . C10 C 1.3086(2) 0.4725(2) 0.84047(5) 0.0295(4) Uani 1 1 d . . . H10 H 1.3738 0.4907 0.8191 0.035 Uiso 1 1 calc R . . C11 C 1.3295(2) 0.5699(2) 0.87046(5) 0.0328(4) Uani 1 1 d . . . H11 H 1.4108 0.6553 0.8701 0.039 Uiso 1 1 calc R . . C12 C 1.2300(2) 0.5407(2) 0.90091(5) 0.0288(4) Uani 1 1 d . . . H12 H 1.2412 0.6059 0.9218 0.035 Uiso 1 1 calc R . . C13 C 1.1135(2) 0.4141(2) 0.90015(4) 0.0231(3) Uani 1 1 d . . . C14 C 0.9994(2) 0.3859(2) 0.93236(4) 0.0245(3) Uani 1 1 d . . . C15 C 0.7327(2) 0.2401(2) 0.94879(4) 0.0269(4) Uani 1 1 d . . . C16 C 0.5882(2) 0.1502(2) 0.93072(4) 0.0229(3) Uani 1 1 d . . . C17 C 0.4451(2) 0.1072(2) 0.95157(4) 0.0256(3) Uani 1 1 d . . . H17 H 0.4402 0.1319 0.9766 0.031 Uiso 1 1 calc R . . C18 C 0.3108(2) 0.0276(2) 0.93469(4) 0.0271(4) Uani 1 1 d . . . H18 H 0.2097 -0.0013 0.9478 0.032 Uiso 1 1 calc R . . C19 C 0.3257(2) -0.0094(2) 0.89832(4) 0.0256(3) Uani 1 1 d . . . H19 H 0.2365 -0.0667 0.8863 0.031 Uiso 1 1 calc R . . C20 C 0.4737(2) 0.0388(2) 0.87978(4) 0.0222(3) Uani 1 1 d . . . C21 C 0.4868(2) -0.0047(2) 0.84032(4) 0.0236(3) Uani 1 1 d . . . C22 C 0.6821(2) -0.2915(2) 0.96628(4) 0.0301(4) Uani 1 1 d . . . H22A H 0.6852 -0.1779 0.9739 0.036 Uiso 1 1 calc R . . H22B H 0.7787 -0.3486 0.9782 0.036 Uiso 1 1 calc R . . C23 C 0.5119(2) -0.3660(3) 0.97663(5) 0.0375(4) Uani 1 1 d . . . H23A H 0.4169 -0.3039 0.9661 0.056 Uiso 1 1 calc R . . H23B H 0.5006 -0.3665 1.0030 0.056 Uiso 1 1 calc R . . H23C H 0.5072 -0.4762 0.9676 0.056 Uiso 1 1 calc R . . C24 C 0.5859(2) 0.0611(2) 0.78212(4) 0.0254(3) Uani 1 1 d . . . H24A H 0.4667 0.0449 0.7730 0.030 Uiso 1 1 calc R . . H24B H 0.6538 -0.0373 0.7774 0.030 Uiso 1 1 calc R . . C25 C 0.6685(3) 0.2023(2) 0.76377(5) 0.0325(4) Uani 1 1 d . . . H25A H 0.6010 0.2991 0.7689 0.049 Uiso 1 1 calc R . . H25B H 0.6713 0.1840 0.7376 0.049 Uiso 1 1 calc R . . H25C H 0.7869 0.2160 0.7728 0.049 Uiso 1 1 calc R . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 O1 0.0368(7) 0.0398(7) 0.0190(5) -0.0019(5) -0.0023(5) -0.0104(6) O2 0.0301(6) 0.0393(7) 0.0164(5) 0.0008(5) 0.0020(5) -0.0071(6) O3 0.0450(7) 0.0322(6) 0.0178(5) 0.0010(5) 0.0055(5) 0.0029(6) O4 0.0320(6) 0.0422(7) 0.0213(5) 0.0058(5) 0.0047(5) -0.0033(6) O5 0.0347(7) 0.0389(7) 0.0244(6) -0.0085(5) -0.0012(5) -0.0057(6) O6 0.0368(7) 0.0643(9) 0.0196(6) -0.0107(6) 0.0026(5) -0.0138(8) O7 0.0479(8) 0.0327(7) 0.0244(6) -0.0023(5) -0.0009(6) -0.0141(7) O8 0.0301(6) 0.0301(6) 0.0162(5) -0.0007(5) -0.0002(5) -0.0051(5) N1 0.0238(6) 0.0250(7) 0.0168(6) -0.0003(5) -0.0007(5) 0.0020(6) N2 0.0340(8) 0.0272(7) 0.0173(6) 0.0004(6) 0.0047(6) -0.0015(7) N3 0.0205(6) 0.0235(6) 0.0195(6) 0.0020(5) -0.0006(5) 0.0013(6) N4 0.0269(7) 0.0326(8) 0.0177(6) -0.0051(6) 0.0011(6) -0.0063(6) N5 0.0218(6) 0.0268(7) 0.0179(6) 0.0004(5) -0.0003(5) 0.0006(6) C1 0.0207(7) 0.0275(8) 0.0176(7) 0.0008(6) -0.0027(6) 0.0018(7) C2 0.0252(8) 0.0273(8) 0.0237(7) 0.0008(7) -0.0010(6) -0.0006(7) C3 0.0328(9) 0.0269(8) 0.0239(8) -0.0051(7) -0.0046(7) 0.0008(8) C4 0.0331(9) 0.0287(8) 0.0172(7) -0.0032(6) -0.0014(6) 0.0053(8) C5 0.0256(8) 0.0252(8) 0.0175(7) 0.0003(6) -0.0014(6) 0.0047(7) C6 0.0244(8) 0.0262(8) 0.0190(7) 0.0016(6) -0.0009(6) -0.0001(7) C7 0.0279(8) 0.0270(8) 0.0199(7) 0.0001(6) 0.0004(6) 0.0056(7) C8 0.0220(7) 0.0295(8) 0.0219(7) 0.0048(6) -0.0001(6) 0.0024(7) C9 0.0226(8) 0.0238(8) 0.0233(7) 0.0048(6) 0.0001(6) 0.0016(7) C10 0.0259(8) 0.0312(9) 0.0315(8) 0.0090(7) 0.0027(7) -0.0020(8) C11 0.0279(9) 0.0280(9) 0.0425(10) 0.0038(8) -0.0002(8) -0.0073(8) C12 0.0278(9) 0.0254(8) 0.0333(9) -0.0022(7) -0.0034(7) -0.0026(7) C13 0.0221(7) 0.0235(8) 0.0236(7) 0.0019(6) -0.0039(6) 0.0006(7) C14 0.0237(8) 0.0272(8) 0.0224(7) -0.0019(7) -0.0024(6) 0.0006(7) C15 0.0249(8) 0.0349(9) 0.0208(7) -0.0013(7) -0.0008(6) -0.0033(8) C16 0.0223(7) 0.0286(8) 0.0177(7) 0.0004(6) -0.0004(6) 0.0009(7) C17 0.0241(8) 0.0332(9) 0.0195(7) -0.0002(7) 0.0017(6) 0.0015(7) C18 0.0224(8) 0.0353(9) 0.0235(7) 0.0035(7) 0.0029(6) 0.0002(8) C19 0.0230(7) 0.0284(8) 0.0254(8) 0.0029(7) -0.0034(6) -0.0015(7) C20 0.0235(8) 0.0251(8) 0.0181(7) 0.0017(6) -0.0021(6) 0.0011(7) C21 0.0242(8) 0.0256(8) 0.0211(7) 0.0013(6) -0.0037(6) 0.0007(7) C22 0.0340(9) 0.0416(10) 0.0149(7) 0.0008(7) 0.0016(7) 0.0000(9) C23 0.0341(9) 0.0546(12) 0.0238(8) 0.0041(8) 0.0065(8) 0.0023(10) C24 0.0320(8) 0.0290(8) 0.0152(7) -0.0017(6) -0.0004(7) -0.0011(7) C25 0.0403(10) 0.0351(10) 0.0221(8) 0.0020(7) 0.0020(7) -0.0056(9) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag O1 C6 1.205(2) . ? O2 C6 1.335(2) . ? O2 C22 1.4675(18) . ? O3 C7 1.2071(19) . ? O4 C8 1.2131(19) . ? O5 C14 1.2115(19) . ? O6 C15 1.209(2) . ? O7 C21 1.209(2) . ? O8 C21 1.330(2) . ? O8 C24 1.4702(18) . ? N1 C1 1.336(2) . ? N1 C5 1.3435(19) . ? N2 C8 1.373(2) . ? N2 C7 1.388(2) . ? N2 H2A 0.89(2) . ? N3 C13 1.336(2) . ? N3 C9 1.339(2) . ? N4 C14 1.382(2) . ? N4 C15 1.386(2) . ? N4 H4A 0.883(18) . ? N5 C20 1.341(2) . ? N5 C16 1.3428(19) . ? C1 C2 1.390(2) . ? C1 C6 1.509(2) . ? C2 C3 1.394(2) . ? C2 H2 0.9500 . ? C3 C4 1.386(2) . ? C3 H3 0.9500 . ? C4 C5 1.386(2) . ? C4 H4 0.9500 . ? C5 C7 1.502(2) . ? C8 C9 1.508(2) . ? C9 C10 1.385(2) . ? C10 C11 1.386(3) . ? C10 H10 0.9500 . ? C11 C12 1.386(3) . ? C11 H11 0.9500 . ? C12 C13 1.389(2) . ? C12 H12 0.9500 . ? C13 C14 1.501(2) . ? C15 C16 1.501(2) . ? C16 C17 1.395(2) . ? C17 C18 1.382(2) . ? C17 H17 0.9500 . ? C18 C19 1.386(2) . ? C18 H18 0.9500 . ? C19 C20 1.393(2) . ? C19 H19 0.9500 . ? C20 C21 1.509(2) . ? C22 C23 1.504(3) . ? C22 H22A 0.9900 . ? C22 H22B 0.9900 . ? C23 H23A 0.9800 . ? C23 H23B 0.9800 . ? C23 H23C 0.9800 . ? C24 C25 1.503(2) . ? C24 H24A 0.9900 . ? C24 H24B 0.9900 . ? C25 H25A 0.9800 . ? C25 H25B 0.9800 . ? C25 H25C 0.9800 . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C6 O2 C22 115.34(14) . . ? C21 O8 C24 114.19(13) . . ? C1 N1 C5 117.28(14) . . ? C8 N2 C7 127.84(14) . . ? C8 N2 H2A 114.8(16) . . ? C7 N2 H2A 116.5(16) . . ? C13 N3 C9 117.49(15) . . ? C14 N4 C15 126.25(14) . . ? C14 N4 H4A 115.9(12) . . ? C15 N4 H4A 117.4(13) . . ? C20 N5 C16 116.47(14) . . ? N1 C1 C2 123.23(15) . . ? N1 C1 C6 114.72(14) . . ? C2 C1 C6 121.98(15) . . ? C1 C2 C3 118.58(16) . . ? C1 C2 H2 120.7 . . ? C3 C2 H2 120.7 . . ? C4 C3 C2 118.85(16) . . ? C4 C3 H3 120.6 . . ? C2 C3 H3 120.6 . . ? C3 C4 C5 118.23(14) . . ? C3 C4 H4 120.9 . . ? C5 C4 H4 120.9 . . ? N1 C5 C4 123.81(16) . . ? N1 C5 C7 116.39(14) . . ? C4 C5 C7 119.80(14) . . ? O1 C6 O2 125.31(15) . . ? O1 C6 C1 123.44(15) . . ? O2 C6 C1 111.25(14) . . ? O3 C7 N2 124.53(16) . . ? O3 C7 C5 122.91(16) . . ? N2 C7 C5 112.55(13) . . ? O4 C8 N2 125.87(16) . . ? O4 C8 C9 121.55(16) . . ? N2 C8 C9 112.55(13) . . ? N3 C9 C10 123.39(16) . . ? N3 C9 C8 116.50(15) . . ? C10 C9 C8 120.11(15) . . ? C9 C10 C11 118.43(16) . . ? C9 C10 H10 120.8 . . ? C11 C10 H10 120.8 . . ? C10 C11 C12 118.96(17) . . ? C10 C11 H11 120.5 . . ? C12 C11 H11 120.5 . . ? C11 C12 C13 118.44(16) . . ? C11 C12 H12 120.8 . . ? C13 C12 H12 120.8 . . ? N3 C13 C12 123.29(15) . . ? N3 C13 C14 117.79(14) . . ? C12 C13 C14 118.89(15) . . ? O5 C14 N4 125.19(16) . . ? O5 C14 C13 121.57(16) . . ? N4 C14 C13 113.16(13) . . ? O6 C15 N4 124.16(16) . . ? O6 C15 C16 122.16(16) . . ? N4 C15 C16 113.62(14) . . ? N5 C16 C17 124.33(15) . . ? N5 C16 C15 117.59(14) . . ? C17 C16 C15 118.06(14) . . ? C18 C17 C16 117.93(15) . . ? C18 C17 H17 121.0 . . ? C16 C17 H17 121.0 . . ? C17 C18 C19 118.97(16) . . ? C17 C18 H18 120.5 . . ? C19 C18 H18 120.5 . . ? C18 C19 C20 118.85(16) . . ? C18 C19 H19 120.6 . . ? C20 C19 H19 120.6 . . ? N5 C20 C19 123.41(15) . . ? N5 C20 C21 119.03(14) . . ? C19 C20 C21 117.56(15) . . ? O7 C21 O8 124.32(15) . . ? O7 C21 C20 121.72(15) . . ? O8 C21 C20 113.91(14) . . ? O2 C22 C23 107.56(15) . . ? O2 C22 H22A 110.2 . . ? C23 C22 H22A 110.2 . . ? O2 C22 H22B 110.2 . . ? C23 C22 H22B 110.2 . . ? H22A C22 H22B 108.5 . . ? C22 C23 H23A 109.5 . . ? C22 C23 H23B 109.5 . . ? H23A C23 H23B 109.5 . . ? C22 C23 H23C 109.5 . . ? H23A C23 H23C 109.5 . . ? H23B C23 H23C 109.5 . . ? O8 C24 C25 107.10(13) . . ? O8 C24 H24A 110.3 . . ? C25 C24 H24A 110.3 . . ? O8 C24 H24B 110.3 . . ? C25 C24 H24B 110.3 . . ? H24A C24 H24B 108.6 . . ? C24 C25 H25A 109.5 . . ? C24 C25 H25B 109.5 . . ? H25A C25 H25B 109.5 . . ? C24 C25 H25C 109.5 . . ? H25A C25 H25C 109.5 . . ? H25B C25 H25C 109.5 . . ? 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 C5 N1 C1 C2 0.8(2) . . . . ? C5 N1 C1 C6 177.89(14) . . . . ? N1 C1 C2 C3 0.5(2) . . . . ? C6 C1 C2 C3 -176.36(16) . . . . ? C1 C2 C3 C4 -1.1(2) . . . . ? C2 C3 C4 C5 0.4(3) . . . . ? C1 N1 C5 C4 -1.6(2) . . . . ? C1 N1 C5 C7 178.22(15) . . . . ? C3 C4 C5 N1 1.0(3) . . . . ? C3 C4 C5 C7 -178.80(16) . . . . ? C22 O2 C6 O1 -4.6(3) . . . . ? C22 O2 C6 C1 174.88(14) . . . . ? N1 C1 C6 O1 -22.3(2) . . . . ? C2 C1 C6 O1 154.87(17) . . . . ? N1 C1 C6 O2 158.25(14) . . . . ? C2 C1 C6 O2 -24.6(2) . . . . ? C8 N2 C7 O3 -11.1(3) . . . . ? C8 N2 C7 C5 169.82(16) . . . . ? N1 C5 C7 O3 176.13(16) . . . . ? C4 C5 C7 O3 -4.0(3) . . . . ? N1 C5 C7 N2 -4.8(2) . . . . ? C4 C5 C7 N2 175.06(15) . . . . ? C7 N2 C8 O4 6.2(3) . . . . ? C7 N2 C8 C9 -171.79(16) . . . . ? C13 N3 C9 C10 0.0(2) . . . . ? C13 N3 C9 C8 179.64(14) . . . . ? O4 C8 C9 N3 171.59(16) . . . . ? N2 C8 C9 N3 -10.3(2) . . . . ? O4 C8 C9 C10 -8.8(3) . . . . ? N2 C8 C9 C10 169.34(15) . . . . ? N3 C9 C10 C11 0.8(3) . . . . ? C8 C9 C10 C11 -178.85(16) . . . . ? C9 C10 C11 C12 -0.9(3) . . . . ? C10 C11 C12 C13 0.3(3) . . . . ? C9 N3 C13 C12 -0.7(2) . . . . ? C9 N3 C13 C14 177.17(14) . . . . ? C11 C12 C13 N3 0.5(3) . . . . ? C11 C12 C13 C14 -177.30(16) . . . . ? C15 N4 C14 O5 5.0(3) . . . . ? C15 N4 C14 C13 -171.73(16) . . . . ? N3 C13 C14 O5 174.27(16) . . . . ? C12 C13 C14 O5 -7.8(2) . . . . ? N3 C13 C14 N4 -8.8(2) . . . . ? C12 C13 C14 N4 169.08(15) . . . . ? C14 N4 C15 O6 -12.8(3) . . . . ? C14 N4 C15 C16 164.59(16) . . . . ? C20 N5 C16 C17 -1.8(2) . . . . ? C20 N5 C16 C15 179.75(15) . . . . ? O6 C15 C16 N5 175.47(18) . . . . ? N4 C15 C16 N5 -2.0(2) . . . . ? O6 C15 C16 C17 -3.1(3) . . . . ? N4 C15 C16 C17 179.48(16) . . . . ? N5 C16 C17 C18 0.2(3) . . . . ? C15 C16 C17 C18 178.59(16) . . . . ? C16 C17 C18 C19 1.6(3) . . . . ? C17 C18 C19 C20 -1.8(3) . . . . ? C16 N5 C20 C19 1.7(2) . . . . ? C16 N5 C20 C21 -177.71(14) . . . . ? C18 C19 C20 N5 0.0(3) . . . . ? C18 C19 C20 C21 179.47(16) . . . . ? C24 O8 C21 O7 1.6(2) . . . . ? C24 O8 C21 C20 -175.88(13) . . . . ? N5 C20 C21 O7 154.22(16) . . . . ? C19 C20 C21 O7 -25.2(2) . . . . ? N5 C20 C21 O8 -28.3(2) . . . . ? C19 C20 C21 O8 152.30(15) . . . . ? C6 O2 C22 C23 168.95(15) . . . . ? C21 O8 C24 C25 168.92(15) . . . . ? 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 N2 H2A N3 0.89(2) 2.18(2) 2.642(2) 112.1(19) . N2 H2A N1 0.89(2) 2.19(2) 2.635(2) 110.8(18) . N4 H4A N3 0.883(18) 2.232(18) 2.675(2) 110.7(14) . _diffrn_measured_fraction_theta_max 0.994 _diffrn_reflns_theta_full 27.87 _diffrn_measured_fraction_theta_full 0.994 _refine_diff_density_max 0.214 _refine_diff_density_min -0.151 _refine_diff_density_rms 0.034