# Electronic Supplementary Material (ESI) for Journal of Materials Chemistry # This journal is © The Royal Society of Chemistry 2011 data_global _journal_name_full J.Mater.Chem. _journal_coden_cambridge 1145 _journal_year ? _journal_volume ? _journal_page_first ? _publ_contact_author_email pangsp@bit.edu.cn _publ_contact_author_name 'Si-Ping Pang' loop_ _publ_author_name 'Qiu-Han Lin' 'Yu-Chuan Li' 'Ya-Yu Li' 'Zhu Wang' 'Wei Liu' 'Cai Qi' 'Si-Ping Pang' # Attachment '- BO529.cif' data_bo529 _database_code_depnum_ccdc_archive 'CCDC 837299' #TrackingRef '- BO529.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C4 H7 N9 O2' _chemical_formula_weight 213.19 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 7.736(7) _cell_length_b 9.684(9) _cell_length_c 12.512(11) _cell_angle_alpha 100.163(15) _cell_angle_beta 98.071(11) _cell_angle_gamma 100.744(9) _cell_volume 891.8(14) _cell_formula_units_Z 4 _cell_measurement_temperature 93(2) _cell_measurement_reflns_used 2579 _cell_measurement_theta_min 3.02 _cell_measurement_theta_max 27.46 _exptl_crystal_description Chunk _exptl_crystal_colour Colorless _exptl_crystal_size_max 0.30 _exptl_crystal_size_mid 0.17 _exptl_crystal_size_min 0.09 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.588 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 440 _exptl_absorpt_coefficient_mu 0.131 _exptl_absorpt_correction_type none _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 93(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'Rotating Anode' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type AFC10/Saturn724+ _diffrn_measurement_method Multi-scan _diffrn_detector_area_resol_mean 28.5714 _diffrn_standards_number 0 _diffrn_standards_interval_count 0 _diffrn_standards_interval_time 0 _diffrn_standards_decay_% 0 _diffrn_reflns_number 6375 _diffrn_reflns_av_R_equivalents 0.0436 _diffrn_reflns_av_sigmaI/netI 0.0828 _diffrn_reflns_limit_h_min -9 _diffrn_reflns_limit_h_max 9 _diffrn_reflns_limit_k_min -11 _diffrn_reflns_limit_k_max 8 _diffrn_reflns_limit_l_min -14 _diffrn_reflns_limit_l_max 14 _diffrn_reflns_theta_min 3.10 _diffrn_reflns_theta_max 26.00 _reflns_number_total 3388 _reflns_number_gt 2052 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'CrystalClear (Rigaku Inc., 2008)' _computing_cell_refinement 'CrystalClear (Rigaku Inc., 2008)' _computing_data_reduction 'CrystalClear (Rigaku Inc., 2008)' _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^)+(0.0256P)^2^+0.3360P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment mixed _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 3388 _refine_ls_number_parameters 289 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0765 _refine_ls_R_factor_gt 0.0472 _refine_ls_wR_factor_ref 0.1054 _refine_ls_wR_factor_gt 0.0995 _refine_ls_goodness_of_fit_ref 0.999 _refine_ls_restrained_S_all 0.999 _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 O1 O 0.7532(2) 1.0474(2) 0.72602(15) 0.0221(5) Uani 1 1 d . . . O2 O 0.4633(3) 1.0128(2) 0.68903(17) 0.0308(5) Uani 1 1 d . . . O3 O 0.7157(3) 0.1645(2) 0.98369(16) 0.0247(5) Uani 1 1 d . . . O4 O 0.9953(3) 0.1625(2) 0.97974(16) 0.0266(5) Uani 1 1 d . . . N1 N 0.7813(3) 1.2179(2) 0.57286(18) 0.0207(5) Uani 1 1 d . . . N2 N 0.7318(3) 1.2939(3) 0.49850(19) 0.0230(6) Uani 1 1 d . . . N3 N 0.5543(3) 1.2812(3) 0.48337(19) 0.0238(6) Uani 1 1 d . . . N4 N 0.4846(3) 1.1955(3) 0.54799(18) 0.0210(5) Uani 1 1 d . . . N5 N 0.6141(3) 1.0676(2) 0.67699(18) 0.0195(5) Uani 1 1 d . . . N6 N 0.7332(3) 0.3750(2) 0.86312(18) 0.0197(5) Uani 1 1 d . . . N7 N 0.8045(3) 0.4849(3) 0.81908(19) 0.0229(6) Uani 1 1 d . . . N8 N 0.9829(3) 0.4999(2) 0.83404(19) 0.0229(6) Uani 1 1 d . . . N9 N 1.0301(3) 0.3993(2) 0.88604(18) 0.0192(5) Uani 1 1 d . . . N10 N 0.8621(3) 0.2105(2) 0.95913(18) 0.0194(5) Uani 1 1 d . . . N11 N 0.5444(3) 0.3894(2) 0.20442(17) 0.0168(5) Uani 1 1 d . . . N12 N 0.5248(3) 0.4084(2) 0.10195(18) 0.0179(5) Uani 1 1 d . . . N13 N 0.4174(3) 0.2864(2) 0.04553(17) 0.0167(5) Uani 1 1 d . . . N14 N 0.3674(3) 0.2607(3) -0.06969(19) 0.0183(5) Uani 1 1 d . . . N15 N 0.9665(3) 0.7804(2) 0.65182(17) 0.0175(5) Uani 1 1 d . . . N16 N 0.9840(3) 0.8915(2) 0.60359(17) 0.0188(5) Uani 1 1 d . . . N17 N 1.0878(3) 0.9977(2) 0.68254(18) 0.0165(5) Uani 1 1 d . . . N18 N 1.1352(3) 1.1368(3) 0.6649(2) 0.0196(6) Uani 1 1 d . . . C1 C 0.6264(3) 1.1609(3) 0.5986(2) 0.0160(6) Uani 1 1 d . . . C2 C 0.8747(4) 0.3288(3) 0.9017(2) 0.0165(6) Uani 1 1 d . . . C3 C 0.3709(4) 0.1915(3) 0.1088(2) 0.0210(6) Uani 1 1 d . . . H3 H 0.2973 0.0977 0.0857 0.025 Uiso 1 1 calc R . . C4 C 0.4534(4) 0.2604(3) 0.2138(2) 0.0218(7) Uani 1 1 d . . . H4 H 0.4476 0.2247 0.2795 0.026 Uiso 1 1 calc R . . C5 C 0.6506(4) 0.5061(3) 0.2937(2) 0.0239(7) Uani 1 1 d . . . H5A H 0.7612 0.5485 0.2709 0.029 Uiso 1 1 calc R . . H5B H 0.6802 0.4679 0.3598 0.029 Uiso 1 1 calc R . . H5C H 0.5815 0.5800 0.3101 0.029 Uiso 1 1 calc R . . C6 C 1.1329(4) 0.9552(3) 0.7768(2) 0.0190(6) Uani 1 1 d . . . H6 H 1.2042 1.0126 0.8436 0.023 Uiso 1 1 calc R . . C7 C 1.0555(4) 0.8126(3) 0.7573(2) 0.0196(6) Uani 1 1 d . . . H7 H 1.0625 0.7494 0.8071 0.024 Uiso 1 1 calc R . . C8 C 0.8646(4) 0.6400(3) 0.5882(2) 0.0227(7) Uani 1 1 d . . . H8A H 0.7471 0.6497 0.5533 0.027 Uiso 1 1 calc R . . H8B H 0.8490 0.5723 0.6375 0.027 Uiso 1 1 calc R . . H8C H 0.9295 0.6042 0.5311 0.027 Uiso 1 1 calc R . . H14A H 0.291(4) 0.311(3) -0.084(2) 0.030(9) Uiso 1 1 d . . . H18A H 1.210(4) 1.130(3) 0.615(2) 0.013(7) Uiso 1 1 d . . . H18B H 1.044(4) 1.169(3) 0.638(2) 0.020(8) Uiso 1 1 d . . . H14B H 0.468(4) 0.300(3) -0.098(2) 0.043(10) Uiso 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 O1 0.0180(11) 0.0275(12) 0.0209(10) 0.0043(9) -0.0005(8) 0.0089(9) O2 0.0209(12) 0.0341(13) 0.0451(13) 0.0211(11) 0.0144(10) 0.0066(10) O3 0.0192(12) 0.0249(12) 0.0328(12) 0.0103(10) 0.0104(9) 0.0032(9) O4 0.0226(12) 0.0275(12) 0.0349(12) 0.0141(10) 0.0052(9) 0.0108(9) N1 0.0192(14) 0.0208(14) 0.0220(13) 0.0054(11) 0.0043(10) 0.0023(10) N2 0.0228(14) 0.0221(14) 0.0250(13) 0.0093(11) 0.0046(11) 0.0027(11) N3 0.0249(14) 0.0267(14) 0.0210(13) 0.0077(11) 0.0040(11) 0.0059(11) N4 0.0179(13) 0.0244(14) 0.0195(12) 0.0040(11) 0.0007(10) 0.0044(10) N5 0.0165(13) 0.0203(14) 0.0217(13) 0.0018(11) 0.0050(10) 0.0057(10) N6 0.0192(13) 0.0190(14) 0.0211(13) 0.0058(11) 0.0034(10) 0.0037(10) N7 0.0222(14) 0.0208(14) 0.0271(13) 0.0085(11) 0.0063(11) 0.0039(10) N8 0.0213(14) 0.0202(14) 0.0284(14) 0.0087(11) 0.0056(11) 0.0035(10) N9 0.0172(13) 0.0180(13) 0.0229(13) 0.0055(11) 0.0047(10) 0.0034(10) N10 0.0195(13) 0.0187(13) 0.0195(13) 0.0013(11) 0.0036(10) 0.0050(10) N11 0.0177(13) 0.0178(13) 0.0151(12) 0.0050(10) 0.0032(10) 0.0031(10) N12 0.0163(13) 0.0160(13) 0.0191(12) 0.0026(10) 0.0023(10) -0.0006(10) N13 0.0134(12) 0.0191(13) 0.0175(12) 0.0044(11) 0.0020(10) 0.0034(10) N14 0.0193(14) 0.0221(14) 0.0130(12) 0.0058(11) 0.0006(10) 0.0031(11) N15 0.0163(13) 0.0169(13) 0.0178(12) 0.0044(10) 0.0008(10) 0.0010(10) N16 0.0163(13) 0.0202(13) 0.0180(12) 0.0023(11) 0.0007(10) 0.0025(10) N17 0.0139(12) 0.0158(13) 0.0197(12) 0.0048(10) 0.0013(10) 0.0027(9) N18 0.0166(13) 0.0182(14) 0.0251(14) 0.0081(11) 0.0028(11) 0.0041(10) C1 0.0158(15) 0.0176(15) 0.0147(14) 0.0021(12) 0.0016(11) 0.0055(12) C2 0.0175(15) 0.0166(15) 0.0146(14) 0.0001(12) 0.0032(11) 0.0047(12) C3 0.0211(16) 0.0161(15) 0.0239(15) 0.0079(13) -0.0001(13) -0.0010(12) C4 0.0223(16) 0.0195(16) 0.0240(16) 0.0086(13) 0.0038(13) 0.0021(12) C5 0.0249(17) 0.0205(16) 0.0200(16) -0.0008(13) 0.0001(13) -0.0035(13) C6 0.0180(15) 0.0224(16) 0.0152(14) 0.0036(13) 0.0010(12) 0.0028(12) C7 0.0163(15) 0.0244(17) 0.0174(15) 0.0061(13) -0.0007(12) 0.0033(12) C8 0.0221(16) 0.0185(16) 0.0232(15) 0.0022(13) -0.0008(12) -0.0007(12) _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 N5 1.228(3) . ? O2 N5 1.230(3) . ? O3 N10 1.238(3) . ? O4 N10 1.222(3) . ? N1 C1 1.330(3) . ? N1 N2 1.342(3) . ? N2 N3 1.339(3) . ? N3 N4 1.351(3) . ? N4 C1 1.317(3) . ? N5 C1 1.447(3) . ? N6 C2 1.320(3) . ? N6 N7 1.346(3) . ? N7 N8 1.343(3) . ? N8 N9 1.340(3) . ? N9 C2 1.326(3) . ? N10 C2 1.451(3) . ? N11 N12 1.319(3) . ? N11 C4 1.348(4) . ? N11 C5 1.467(3) . ? N12 N13 1.327(3) . ? N13 C3 1.346(3) . ? N13 N14 1.404(3) . ? N14 H14A 0.85(3) . ? N14 H14B 0.95(3) . ? N15 N16 1.319(3) . ? N15 C7 1.354(3) . ? N15 C8 1.464(3) . ? N16 N17 1.338(3) . ? N17 C6 1.339(3) . ? N17 N18 1.394(3) . ? N18 H18A 0.91(3) . ? N18 H18B 0.87(3) . ? C3 C4 1.369(4) . ? C3 H3 0.9500 . ? C4 H4 0.9500 . ? C5 H5A 0.9800 . ? C5 H5B 0.9800 . ? C5 H5C 0.9800 . ? C6 C7 1.362(4) . ? C6 H6 0.9500 . ? C7 H7 0.9500 . ? C8 H8A 0.9800 . ? C8 H8B 0.9800 . ? C8 H8C 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 C1 N1 N2 102.7(2) . . ? N3 N2 N1 109.7(2) . . ? N2 N3 N4 109.2(2) . . ? C1 N4 N3 103.0(2) . . ? O1 N5 O2 124.5(2) . . ? O1 N5 C1 118.4(2) . . ? O2 N5 C1 117.1(2) . . ? C2 N6 N7 102.9(2) . . ? N8 N7 N6 109.2(2) . . ? N9 N8 N7 109.6(2) . . ? C2 N9 N8 102.8(2) . . ? O4 N10 O3 124.2(2) . . ? O4 N10 C2 118.3(2) . . ? O3 N10 C2 117.5(2) . . ? N12 N11 C4 113.0(2) . . ? N12 N11 C5 119.5(2) . . ? C4 N11 C5 127.4(2) . . ? N11 N12 N13 103.2(2) . . ? N12 N13 C3 113.5(2) . . ? N12 N13 N14 121.4(2) . . ? C3 N13 N14 125.0(2) . . ? N13 N14 H14A 108(2) . . ? N13 N14 H14B 107.7(19) . . ? H14A N14 H14B 105(3) . . ? N16 N15 C7 113.0(2) . . ? N16 N15 C8 119.2(2) . . ? C7 N15 C8 127.8(2) . . ? N15 N16 N17 103.2(2) . . ? N16 N17 C6 112.8(2) . . ? N16 N17 N18 121.3(2) . . ? C6 N17 N18 125.9(2) . . ? N17 N18 H18A 104.4(16) . . ? N17 N18 H18B 113.1(19) . . ? H18A N18 H18B 109(2) . . ? N4 C1 N1 115.3(2) . . ? N4 C1 N5 122.2(2) . . ? N1 C1 N5 122.5(2) . . ? N6 C2 N9 115.4(2) . . ? N6 C2 N10 122.5(2) . . ? N9 C2 N10 122.1(2) . . ? N13 C3 C4 104.7(3) . . ? N13 C3 H3 127.7 . . ? C4 C3 H3 127.7 . . ? N11 C4 C3 105.6(2) . . ? N11 C4 H4 127.2 . . ? C3 C4 H4 127.2 . . ? N11 C5 H5A 109.5 . . ? N11 C5 H5B 109.5 . . ? H5A C5 H5B 109.5 . . ? N11 C5 H5C 109.5 . . ? H5A C5 H5C 109.5 . . ? H5B C5 H5C 109.5 . . ? N17 C6 C7 105.8(2) . . ? N17 C6 H6 127.1 . . ? C7 C6 H6 127.1 . . ? N15 C7 C6 105.2(2) . . ? N15 C7 H7 127.4 . . ? C6 C7 H7 127.4 . . ? N15 C8 H8A 109.5 . . ? N15 C8 H8B 109.5 . . ? H8A C8 H8B 109.5 . . ? N15 C8 H8C 109.5 . . ? H8A C8 H8C 109.5 . . ? H8B C8 H8C 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 C1 N1 N2 N3 0.5(3) . . . . ? N1 N2 N3 N4 -0.2(3) . . . . ? N2 N3 N4 C1 -0.2(3) . . . . ? C2 N6 N7 N8 -0.5(3) . . . . ? N6 N7 N8 N9 1.0(3) . . . . ? N7 N8 N9 C2 -1.0(3) . . . . ? C4 N11 N12 N13 0.0(3) . . . . ? C5 N11 N12 N13 -177.4(2) . . . . ? N11 N12 N13 C3 -0.7(3) . . . . ? N11 N12 N13 N14 -177.8(2) . . . . ? C7 N15 N16 N17 -0.3(3) . . . . ? C8 N15 N16 N17 -177.7(2) . . . . ? N15 N16 N17 C6 -0.3(3) . . . . ? N15 N16 N17 N18 -178.5(2) . . . . ? N3 N4 C1 N1 0.6(3) . . . . ? N3 N4 C1 N5 -179.6(2) . . . . ? N2 N1 C1 N4 -0.7(3) . . . . ? N2 N1 C1 N5 179.5(2) . . . . ? O1 N5 C1 N4 -175.5(2) . . . . ? O2 N5 C1 N4 5.1(4) . . . . ? O1 N5 C1 N1 4.3(4) . . . . ? O2 N5 C1 N1 -175.1(2) . . . . ? N7 N6 C2 N9 -0.1(3) . . . . ? N7 N6 C2 N10 178.9(2) . . . . ? N8 N9 C2 N6 0.7(3) . . . . ? N8 N9 C2 N10 -178.3(2) . . . . ? O4 N10 C2 N6 170.8(2) . . . . ? O3 N10 C2 N6 -8.9(4) . . . . ? O4 N10 C2 N9 -10.3(4) . . . . ? O3 N10 C2 N9 170.0(2) . . . . ? N12 N13 C3 C4 1.1(3) . . . . ? N14 N13 C3 C4 178.1(2) . . . . ? N12 N11 C4 C3 0.6(3) . . . . ? C5 N11 C4 C3 177.8(3) . . . . ? N13 C3 C4 N11 -1.0(3) . . . . ? N16 N17 C6 C7 0.8(3) . . . . ? N18 N17 C6 C7 178.8(2) . . . . ? N16 N15 C7 C6 0.7(3) . . . . ? C8 N15 C7 C6 177.9(2) . . . . ? N17 C6 C7 N15 -0.9(3) . . . . ? _diffrn_measured_fraction_theta_max 0.967 _diffrn_reflns_theta_full 26.00 _diffrn_measured_fraction_theta_full 0.967 _refine_diff_density_max 0.313 _refine_diff_density_min -0.321 _refine_diff_density_rms 0.079 # Attachment '- BO624.cif' data_bo624 _database_code_depnum_ccdc_archive 'CCDC 837300' #TrackingRef '- BO624.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C8 H14 N18' _chemical_formula_weight 362.37 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' _symmetry_cell_setting Monoclinic _symmetry_space_group_name_H-M P2(1)/c loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y-1/2, z-1/2' _cell_length_a 5.6810(16) _cell_length_b 7.222(2) _cell_length_c 19.096(6) _cell_angle_alpha 90.00 _cell_angle_beta 97.778(4) _cell_angle_gamma 90.00 _cell_volume 776.3(4) _cell_formula_units_Z 2 _cell_measurement_temperature 133(2) _cell_measurement_reflns_used 2284 _cell_measurement_theta_min 3.02 _cell_measurement_theta_max 27.48 _exptl_crystal_description Block _exptl_crystal_colour Yellow _exptl_crystal_size_max 0.40 _exptl_crystal_size_mid 0.33 _exptl_crystal_size_min 0.20 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.550 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 376 _exptl_absorpt_coefficient_mu 0.117 _exptl_absorpt_correction_type none _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 133(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'Rotating Anode' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type AFC10/Saturn724+ _diffrn_measurement_method 'phi and omega scans' _diffrn_detector_area_resol_mean 28.5714 _diffrn_standards_number 0 _diffrn_standards_interval_count 0 _diffrn_standards_interval_time 0 _diffrn_standards_decay_% 0 _diffrn_reflns_number 5842 _diffrn_reflns_av_R_equivalents 0.0236 _diffrn_reflns_av_sigmaI/netI 0.0247 _diffrn_reflns_limit_h_min -7 _diffrn_reflns_limit_h_max 7 _diffrn_reflns_limit_k_min -9 _diffrn_reflns_limit_k_max 8 _diffrn_reflns_limit_l_min -24 _diffrn_reflns_limit_l_max 24 _diffrn_reflns_theta_min 3.55 _diffrn_reflns_theta_max 27.44 _reflns_number_total 1760 _reflns_number_gt 1489 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'CrystalClear (Rigaku Inc., 2008)' _computing_cell_refinement 'CrystalClear (Rigaku Inc., 2008)' _computing_data_reduction 'CrystalClear (Rigaku Inc., 2008)' _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^)+(0.0516P)^2^+0.2090P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment mixed _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 1760 _refine_ls_number_parameters 127 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0450 _refine_ls_R_factor_gt 0.0353 _refine_ls_wR_factor_ref 0.0935 _refine_ls_wR_factor_gt 0.0884 _refine_ls_goodness_of_fit_ref 1.002 _refine_ls_restrained_S_all 1.002 _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 0.41620(19) 0.77222(15) 0.49668(6) 0.0212(3) Uani 1 1 d . . . N2 N 0.53636(19) 0.74058(16) 0.44230(6) 0.0237(3) Uani 1 1 d . . . N3 N 0.43367(19) 0.83295(17) 0.38590(6) 0.0229(3) Uani 1 1 d . . . N4 N 0.24525(19) 0.92693(16) 0.40253(6) 0.0202(3) Uani 1 1 d . . . N5 N 0.08046(18) 0.94858(14) 0.51560(6) 0.0183(2) Uani 1 1 d . . . N6 N 0.14891(19) 0.44791(15) 0.34866(5) 0.0182(2) Uani 1 1 d . . . N7 N 0.06008(18) 0.52275(15) 0.28681(5) 0.0195(3) Uani 1 1 d . . . N8 N 0.22341(18) 0.48599(14) 0.24622(5) 0.0169(2) Uani 1 1 d . . . N9 N 0.1959(2) 0.55692(16) 0.17772(6) 0.0211(3) Uani 1 1 d . . . C1 C 0.2408(2) 0.88626(17) 0.47076(6) 0.0176(3) Uani 1 1 d . . . C2 C 0.4116(2) 0.39352(19) 0.27981(7) 0.0217(3) Uani 1 1 d . . . H2 H 0.5495 0.3541 0.2609 0.026 Uiso 1 1 calc R . . C3 C 0.3610(2) 0.36898(18) 0.34692(7) 0.0221(3) Uani 1 1 d . . . H3 H 0.4567 0.3083 0.3847 0.027 Uiso 1 1 calc R . . C4 C 0.0147(3) 0.4590(2) 0.40856(7) 0.0251(3) Uani 1 1 d . . . H4A H -0.0801 0.5728 0.4051 0.030 Uiso 1 1 calc R . . H4B H 0.1251 0.4601 0.4527 0.030 Uiso 1 1 calc R . . H4C H -0.0908 0.3516 0.4081 0.030 Uiso 1 1 calc R . . H9A H 0.050(3) 0.520(2) 0.1558(9) 0.031(4) Uiso 1 1 d . . . H9B H 0.305(3) 0.495(3) 0.1520(9) 0.041(5) Uiso 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 0.0209(5) 0.0212(5) 0.0208(6) -0.0002(4) 0.0005(4) -0.0010(4) N2 0.0214(6) 0.0242(6) 0.0251(6) -0.0028(5) 0.0019(5) -0.0008(4) N3 0.0205(5) 0.0279(6) 0.0206(5) -0.0025(5) 0.0041(4) -0.0018(5) N4 0.0191(5) 0.0257(6) 0.0158(5) -0.0003(4) 0.0026(4) -0.0015(4) N5 0.0189(5) 0.0195(5) 0.0161(5) 0.0007(4) 0.0007(4) -0.0021(4) N6 0.0208(5) 0.0202(5) 0.0132(5) -0.0002(4) 0.0007(4) -0.0029(4) N7 0.0182(5) 0.0241(6) 0.0160(5) 0.0002(4) 0.0018(4) -0.0001(4) N8 0.0174(5) 0.0187(5) 0.0141(5) 0.0001(4) 0.0011(4) -0.0018(4) N9 0.0228(6) 0.0272(6) 0.0126(5) 0.0032(4) 0.0001(4) -0.0013(5) C1 0.0176(6) 0.0188(6) 0.0157(6) -0.0005(5) -0.0003(5) -0.0040(5) C2 0.0191(6) 0.0252(7) 0.0205(6) 0.0013(5) 0.0013(5) 0.0038(5) C3 0.0228(6) 0.0227(6) 0.0199(6) 0.0026(5) -0.0007(5) 0.0012(5) C4 0.0293(7) 0.0303(7) 0.0171(6) -0.0025(5) 0.0084(5) -0.0047(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 1.3352(17) . ? N1 N2 1.3373(16) . ? N2 N3 1.3324(16) . ? N3 N4 1.3414(16) . ? N4 C1 1.3393(16) . ? N5 N5 1.263(2) 3_576 ? N5 C1 1.4059(17) . ? N6 N7 1.3344(14) . ? N6 C3 1.3373(17) . ? N6 C4 1.4601(17) . ? N7 N8 1.3141(15) . ? N8 C2 1.3472(16) . ? N8 N9 1.3937(15) . ? N9 H9A 0.915(18) . ? N9 H9B 0.952(19) . ? C2 C3 1.3623(18) . ? C2 H2 0.9500 . ? C3 H3 0.9500 . ? C4 H4A 0.9800 . ? C4 H4B 0.9800 . ? C4 H4C 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 C1 N1 N2 104.55(10) . . ? N3 N2 N1 109.18(10) . . ? N2 N3 N4 109.76(10) . . ? C1 N4 N3 103.89(11) . . ? N5 N5 C1 112.85(13) 3_576 . ? N7 N6 C3 112.62(10) . . ? N7 N6 C4 119.75(11) . . ? C3 N6 C4 127.62(11) . . ? N8 N7 N6 103.16(10) . . ? N7 N8 C2 113.42(10) . . ? N7 N8 N9 118.74(10) . . ? C2 N8 N9 127.60(11) . . ? N8 N9 H9A 107.6(10) . . ? N8 N9 H9B 108.2(11) . . ? H9A N9 H9B 103.6(15) . . ? N1 C1 N4 112.62(11) . . ? N1 C1 N5 118.96(11) . . ? N4 C1 N5 128.42(11) . . ? N8 C2 C3 104.92(11) . . ? N8 C2 H2 127.5 . . ? C3 C2 H2 127.5 . . ? N6 C3 C2 105.87(11) . . ? N6 C3 H3 127.1 . . ? C2 C3 H3 127.1 . . ? N6 C4 H4A 109.5 . . ? N6 C4 H4B 109.5 . . ? H4A C4 H4B 109.5 . . ? N6 C4 H4C 109.5 . . ? H4A C4 H4C 109.5 . . ? H4B C4 H4C 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 C1 N1 N2 N3 -0.25(13) . . . . ? N1 N2 N3 N4 0.20(14) . . . . ? N2 N3 N4 C1 -0.06(13) . . . . ? C3 N6 N7 N8 0.61(14) . . . . ? C4 N6 N7 N8 -179.51(10) . . . . ? N6 N7 N8 C2 -0.70(14) . . . . ? N6 N7 N8 N9 -175.46(10) . . . . ? N2 N1 C1 N4 0.22(14) . . . . ? N2 N1 C1 N5 -179.41(10) . . . . ? N3 N4 C1 N1 -0.10(14) . . . . ? N3 N4 C1 N5 179.48(12) . . . . ? N5 N5 C1 N1 -178.23(13) 3_576 . . . ? N5 N5 C1 N4 2.2(2) 3_576 . . . ? N7 N8 C2 C3 0.53(15) . . . . ? N9 N8 C2 C3 174.73(12) . . . . ? N7 N6 C3 C2 -0.31(15) . . . . ? C4 N6 C3 C2 179.82(12) . . . . ? N8 C2 C3 N6 -0.12(14) . . . . ? _diffrn_measured_fraction_theta_max 0.994 _diffrn_reflns_theta_full 27.44 _diffrn_measured_fraction_theta_full 0.994 _refine_diff_density_max 0.270 _refine_diff_density_min -0.214 _refine_diff_density_rms 0.042 data_bo145 _database_code_depnum_ccdc_archive 'CCDC 842816' #TrackingRef '- BO145 (2).cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C3 H5 N9 O2' _chemical_formula_weight 199.16 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 P2(1)/c loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y-1/2, z-1/2' _cell_length_a 15.592(4) _cell_length_b 10.246(2) _cell_length_c 9.813(2) _cell_angle_alpha 90.00 _cell_angle_beta 90.405(4) _cell_angle_gamma 90.00 _cell_volume 1567.6(6) _cell_formula_units_Z 8 _cell_measurement_temperature 93(2) _cell_measurement_reflns_used 4598 _cell_measurement_theta_min 3.15 _cell_measurement_theta_max 27.49 _exptl_crystal_description Platelet _exptl_crystal_colour Colorless _exptl_crystal_size_max 0.37 _exptl_crystal_size_mid 0.27 _exptl_crystal_size_min 0.08 _exptl_crystal_density_meas 0 _exptl_crystal_density_diffrn 1.688 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 816 _exptl_absorpt_coefficient_mu 0.142 _exptl_absorpt_correction_type Multi-scans _exptl_absorpt_correction_T_min 0.9496 _exptl_absorpt_correction_T_max 0.9887 _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 93(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'Rotating Anode' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type AFC10/Saturn724+ _diffrn_measurement_method 'phi and omega scans' _diffrn_detector_area_resol_mean 28.5714 _diffrn_standards_number 0 _diffrn_standards_interval_count 0 _diffrn_standards_interval_time 0 _diffrn_standards_decay_% 0 _diffrn_reflns_number 12555 _diffrn_reflns_av_R_equivalents 0.0289 _diffrn_reflns_av_sigmaI/netI 0.0291 _diffrn_reflns_limit_h_min -15 _diffrn_reflns_limit_h_max 20 _diffrn_reflns_limit_k_min -13 _diffrn_reflns_limit_k_max 12 _diffrn_reflns_limit_l_min -12 _diffrn_reflns_limit_l_max 12 _diffrn_reflns_theta_min 3.15 _diffrn_reflns_theta_max 27.48 _reflns_number_total 3578 _reflns_number_gt 3104 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'CrystalClear (Rigaku Inc., 2008)' _computing_cell_refinement 'CrystalClear (Rigaku Inc., 2008)' _computing_data_reduction 'CrystalClear (Rigaku Inc., 2008)' _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^)+(0.0689P)^2^+0.9890P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment mixed _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 3578 _refine_ls_number_parameters 287 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0636 _refine_ls_R_factor_gt 0.0533 _refine_ls_wR_factor_ref 0.1374 _refine_ls_wR_factor_gt 0.1291 _refine_ls_goodness_of_fit_ref 0.998 _refine_ls_restrained_S_all 0.998 _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 0.29415(9) 0.01673(12) 0.69211(14) 0.0247(3) Uani 1 1 d . . . O2 O 0.24440(8) 0.21374(13) 0.71674(13) 0.0233(3) Uani 1 1 d . . . O3 O 0.20710(9) -0.23301(12) 0.30779(13) 0.0248(3) Uani 1 1 d . . . O4 O 0.24461(9) -0.03249(13) 0.26558(14) 0.0268(3) Uani 1 1 d . . . N1 N 0.38660(9) 0.09078(14) 0.47488(14) 0.0180(3) Uani 1 1 d . . . N2 N 0.42493(9) 0.16553(14) 0.38206(15) 0.0188(3) Uani 1 1 d . . . N3 N 0.40292(10) 0.28913(14) 0.40253(16) 0.0197(3) Uani 1 1 d . . . N4 N 0.34939(9) 0.29754(14) 0.50862(15) 0.0192(3) Uani 1 1 d . . . N5 N 0.28956(9) 0.13348(14) 0.66062(14) 0.0178(3) Uani 1 1 d . . . N6 N 0.11573(10) -0.15616(15) 0.52547(15) 0.0217(3) Uani 1 1 d . . . N7 N 0.07684(11) -0.08025(15) 0.61633(16) 0.0244(4) Uani 1 1 d . . . N8 N 0.09253(11) 0.04368(15) 0.58776(16) 0.0237(4) Uani 1 1 d . . . N9 N 0.14251(10) 0.05126(15) 0.47722(16) 0.0220(3) Uani 1 1 d . . . N10 N 0.20536(9) -0.11470(15) 0.33065(14) 0.0187(3) Uani 1 1 d . . . N11 N 0.38848(9) 0.82361(15) 0.47705(15) 0.0180(3) Uani 1 1 d . . . N12 N 0.43980(10) 0.76533(14) 0.38800(15) 0.0184(3) Uani 1 1 d . . . N13 N 0.42897(9) 0.64039(14) 0.41359(15) 0.0169(3) Uani 1 1 d . . . N14 N 0.48074(10) 0.55067(15) 0.34972(16) 0.0204(3) Uani 1 1 d . . . N15 N 0.11486(10) 0.57463(15) 0.52265(15) 0.0191(3) Uani 1 1 d . A . N16 N 0.06887(10) 0.51888(14) 0.62029(16) 0.0210(3) Uani 1 1 d . A . N17 N 0.07996(10) 0.39367(14) 0.59778(16) 0.0222(3) Uani 1 1 d . . . C1 C 0.34183(10) 0.17504(17) 0.54793(17) 0.0161(3) Uani 1 1 d . . . C2 C 0.15403(11) -0.07186(17) 0.44352(17) 0.0164(4) Uani 1 1 d . . . C3 C 0.34650(11) 0.73786(17) 0.55578(18) 0.0189(4) Uani 1 1 d . . . H3 H 0.3067 0.7575 0.6256 0.023 Uiso 1 1 calc R . . C4 C 0.37239(11) 0.61731(17) 0.51550(17) 0.0179(4) Uani 1 1 d . . . H4 H 0.3548 0.5352 0.5507 0.022 Uiso 1 1 calc R . . C5 C 0.15362(11) 0.48724(18) 0.44227(18) 0.0195(4) Uani 1 1 d . . . H5 H 0.1896 0.5051 0.3668 0.023 Uiso 1 1 calc R A . C6 C 0.13105(11) 0.36770(18) 0.49073(19) 0.0207(4) Uani 1 1 d . A . H6 H 0.1476 0.2846 0.4568 0.025 Uiso 1 1 calc R . . N18 N 0.0565(9) 0.3082(5) 0.7072(14) 0.022(3) Uani 0.44(3) 1 d P A 1 N18' N 0.0250(6) 0.3042(3) 0.6578(10) 0.0193(17) Uani 0.56(3) 1 d P A 2 H11 H 0.3895(15) 0.922(3) 0.477(2) 0.040(7) Uiso 1 1 d . . . H15 H 0.1165(17) 0.669(3) 0.518(3) 0.053(8) Uiso 1 1 d . . . H14A H 0.4976(15) 0.586(2) 0.268(2) 0.033(6) Uiso 1 1 d . . . H14B H 0.4513(15) 0.474(2) 0.336(2) 0.031(6) Uiso 1 1 d . . . H18A H 0.0076(16) 0.340(2) 0.740(3) 0.032(6) Uiso 1 1 d . . . H18B H 0.0520(16) 0.231(2) 0.663(3) 0.035(7) Uiso 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 O1 0.0293(7) 0.0165(7) 0.0283(7) 0.0052(5) 0.0049(6) -0.0004(5) O2 0.0242(7) 0.0222(7) 0.0235(7) -0.0032(5) 0.0054(5) 0.0031(5) O3 0.0320(7) 0.0159(7) 0.0265(7) -0.0048(5) 0.0057(6) 0.0002(5) O4 0.0288(7) 0.0250(8) 0.0266(7) 0.0039(5) 0.0084(6) -0.0042(6) N1 0.0197(7) 0.0144(7) 0.0198(7) 0.0006(6) 0.0037(6) -0.0006(6) N2 0.0215(7) 0.0146(7) 0.0204(7) 0.0009(6) 0.0029(6) -0.0012(6) N3 0.0214(7) 0.0150(8) 0.0225(7) 0.0004(6) 0.0039(6) -0.0005(6) N4 0.0203(7) 0.0149(8) 0.0223(7) -0.0003(6) 0.0014(6) -0.0008(6) N5 0.0185(7) 0.0170(7) 0.0179(7) 0.0008(6) 0.0012(6) -0.0001(6) N6 0.0280(8) 0.0159(8) 0.0214(8) -0.0011(6) 0.0082(6) 0.0002(6) N7 0.0331(9) 0.0158(8) 0.0245(8) -0.0016(6) 0.0095(7) -0.0004(7) N8 0.0301(8) 0.0172(8) 0.0239(8) -0.0025(6) 0.0066(6) -0.0025(7) N9 0.0262(8) 0.0159(8) 0.0241(8) -0.0011(6) 0.0062(6) -0.0018(6) N10 0.0180(7) 0.0196(8) 0.0185(7) -0.0004(6) 0.0018(6) -0.0006(6) N11 0.0198(7) 0.0138(8) 0.0202(7) -0.0008(6) 0.0031(6) 0.0006(6) N12 0.0226(7) 0.0130(7) 0.0197(7) 0.0004(6) 0.0015(6) -0.0002(6) N13 0.0189(7) 0.0122(7) 0.0196(7) 0.0003(6) 0.0004(6) -0.0002(6) N14 0.0238(8) 0.0145(8) 0.0229(8) -0.0026(6) 0.0070(6) 0.0010(6) N15 0.0220(8) 0.0136(8) 0.0218(8) 0.0013(6) 0.0023(6) -0.0001(6) N16 0.0245(8) 0.0134(8) 0.0251(8) 0.0014(6) 0.0082(6) 0.0012(6) N17 0.0254(8) 0.0121(7) 0.0294(8) 0.0026(6) 0.0105(6) 0.0017(6) C1 0.0164(8) 0.0144(8) 0.0175(8) 0.0006(6) 0.0008(6) -0.0020(6) C2 0.0185(8) 0.0147(8) 0.0160(8) -0.0007(6) 0.0024(6) -0.0016(7) C3 0.0179(8) 0.0176(9) 0.0211(8) 0.0017(7) 0.0012(7) 0.0000(7) C4 0.0189(8) 0.0157(9) 0.0192(8) 0.0025(7) 0.0026(7) -0.0010(7) C5 0.0199(8) 0.0186(9) 0.0201(8) 0.0006(7) 0.0024(7) 0.0014(7) C6 0.0201(8) 0.0165(9) 0.0257(9) -0.0010(7) 0.0058(7) 0.0031(7) N18 0.027(4) 0.014(2) 0.025(4) 0.0028(18) 0.012(4) 0.0011(19) N18' 0.021(3) 0.0125(15) 0.024(3) 0.0022(13) 0.006(3) 0.0015(14) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag O1 N5 1.2374(19) . ? O2 N5 1.2169(19) . ? O3 N10 1.2331(19) . ? O4 N10 1.2236(19) . ? N1 C1 1.324(2) . ? N1 N2 1.334(2) . ? N2 N3 1.328(2) . ? N3 N4 1.342(2) . ? N4 C1 1.319(2) . ? N5 C1 1.443(2) . ? N6 C2 1.325(2) . ? N6 N7 1.332(2) . ? N7 N8 1.323(2) . ? N8 N9 1.342(2) . ? N9 C2 1.317(2) . ? N10 C2 1.440(2) . ? N11 N12 1.331(2) . ? N11 C3 1.343(2) . ? N11 H11 1.01(3) . ? N12 N13 1.316(2) . ? N13 C4 1.359(2) . ? N13 N14 1.377(2) . ? N14 H14A 0.92(2) . ? N14 H14B 0.92(2) . ? N15 N16 1.330(2) . ? N15 C5 1.340(2) . ? N15 H15 0.97(3) . ? N16 N17 1.313(2) . ? N17 C6 1.349(2) . ? N17 N18' 1.389(4) . ? N17 N18 1.435(7) . ? C3 C4 1.359(2) . ? C3 H3 0.9500 . ? C4 H4 0.9500 . ? C5 C6 1.361(2) . ? C5 H5 0.9500 . ? C6 H6 0.9500 . ? N18 H18A 0.89(3) . ? N18 H18B 0.91(3) . ? N18' H18A 0.93(3) . ? N18' H18B 0.86(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 C1 N1 N2 103.63(14) . . ? N3 N2 N1 109.07(14) . . ? N2 N3 N4 109.97(14) . . ? C1 N4 N3 102.89(14) . . ? O2 N5 O1 124.95(15) . . ? O2 N5 C1 118.63(14) . . ? O1 N5 C1 116.41(14) . . ? C2 N6 N7 103.58(15) . . ? N8 N7 N6 109.43(15) . . ? N7 N8 N9 109.63(14) . . ? C2 N9 N8 103.21(14) . . ? O4 N10 O3 124.75(15) . . ? O4 N10 C2 118.33(15) . . ? O3 N10 C2 116.92(14) . . ? N12 N11 C3 112.45(15) . . ? N12 N11 H11 115.9(14) . . ? C3 N11 H11 131.6(14) . . ? N13 N12 N11 103.46(14) . . ? N12 N13 C4 113.24(14) . . ? N12 N13 N14 119.09(14) . . ? C4 N13 N14 127.18(15) . . ? N13 N14 H14A 107.7(15) . . ? N13 N14 H14B 110.2(14) . . ? H14A N14 H14B 111(2) . . ? N16 N15 C5 112.64(15) . . ? N16 N15 H15 118.6(16) . . ? C5 N15 H15 128.7(16) . . ? N17 N16 N15 103.06(14) . . ? N16 N17 C6 113.75(15) . . ? N16 N17 N18' 119.38(19) . . ? C6 N17 N18' 124.7(3) . . ? N16 N17 N18 115.8(3) . . ? C6 N17 N18 128.1(2) . . ? N18' N17 N18 28.2(3) . . ? N4 C1 N1 114.44(15) . . ? N4 C1 N5 123.87(15) . . ? N1 C1 N5 121.69(15) . . ? N9 C2 N6 114.15(16) . . ? N9 C2 N10 124.26(16) . . ? N6 C2 N10 121.57(15) . . ? N11 C3 C4 106.28(16) . . ? N11 C3 H3 126.9 . . ? C4 C3 H3 126.9 . . ? C3 C4 N13 104.57(15) . . ? C3 C4 H4 127.7 . . ? N13 C4 H4 127.7 . . ? N15 C5 C6 106.07(16) . . ? N15 C5 H5 127.0 . . ? C6 C5 H5 127.0 . . ? N17 C6 C5 104.48(16) . . ? N17 C6 H6 127.8 . . ? C5 C6 H6 127.8 . . ? N17 N18 H18A 105.6(18) . . ? N17 N18 H18B 101.4(18) . . ? H18A N18 H18B 115(3) . . ? N17 N18' H18A 107.0(16) . . ? N17 N18' H18B 107.4(17) . . ? H18A N18' H18B 116(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 C1 N1 N2 N3 0.41(18) . . . . ? N1 N2 N3 N4 -0.35(19) . . . . ? N2 N3 N4 C1 0.14(18) . . . . ? C2 N6 N7 N8 -0.2(2) . . . . ? N6 N7 N8 N9 -0.2(2) . . . . ? N7 N8 N9 C2 0.5(2) . . . . ? C3 N11 N12 N13 -0.22(18) . . . . ? N11 N12 N13 C4 0.18(18) . . . . ? N11 N12 N13 N14 -172.44(14) . . . . ? C5 N15 N16 N17 -0.25(19) . . . . ? N15 N16 N17 C6 0.2(2) . . . . ? N15 N16 N17 N18' -164.0(6) . . . . ? N15 N16 N17 N18 164.4(8) . . . . ? N3 N4 C1 N1 0.14(19) . . . . ? N3 N4 C1 N5 -179.80(15) . . . . ? N2 N1 C1 N4 -0.34(19) . . . . ? N2 N1 C1 N5 179.59(14) . . . . ? O2 N5 C1 N4 5.9(2) . . . . ? O1 N5 C1 N4 -174.49(15) . . . . ? O2 N5 C1 N1 -174.00(15) . . . . ? O1 N5 C1 N1 5.6(2) . . . . ? N8 N9 C2 N6 -0.7(2) . . . . ? N8 N9 C2 N10 -178.91(16) . . . . ? N7 N6 C2 N9 0.5(2) . . . . ? N7 N6 C2 N10 178.85(15) . . . . ? O4 N10 C2 N9 4.0(3) . . . . ? O3 N10 C2 N9 -176.83(16) . . . . ? O4 N10 C2 N6 -174.17(16) . . . . ? O3 N10 C2 N6 5.0(2) . . . . ? N12 N11 C3 C4 0.2(2) . . . . ? N11 C3 C4 N13 -0.06(18) . . . . ? N12 N13 C4 C3 -0.08(19) . . . . ? N14 N13 C4 C3 171.82(16) . . . . ? N16 N15 C5 C6 0.2(2) . . . . ? N16 N17 C6 C5 -0.1(2) . . . . ? N18' N17 C6 C5 163.1(6) . . . . ? N18 N17 C6 C5 -161.9(9) . . . . ? N15 C5 C6 N17 -0.06(19) . . . . ? _diffrn_measured_fraction_theta_max 0.993 _diffrn_reflns_theta_full 27.48 _diffrn_measured_fraction_theta_full 0.993 _refine_diff_density_max 0.301 _refine_diff_density_min -0.243 _refine_diff_density_rms 0.053