# 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 2012 ####################################################################### # # 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_3-check _database_code_depnum_ccdc_archive 'CCDC 873915' #TrackingRef '3-check.CIF' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C26 H24 N8 O12' _chemical_formula_sum 'C26 H24 N8 O12' _chemical_formula_weight 640.53 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' _symmetry_space_group_name_Hall '-P 1' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 7.4234(15) _cell_length_b 11.738(2) _cell_length_c 17.698(4) _cell_angle_alpha 102.99(3) _cell_angle_beta 100.52(3) _cell_angle_gamma 101.26(3) _cell_volume 1431.8(5) _cell_formula_units_Z 2 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 14831 _cell_measurement_theta_min 3.0 _cell_measurement_theta_max 27.5 _exptl_crystal_description block _exptl_crystal_colour colorless _exptl_crystal_size_max 0.35 _exptl_crystal_size_mid 0.22 _exptl_crystal_size_min 0.20 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.486 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 664 _exptl_absorpt_coefficient_mu 0.120 _exptl_absorpt_correction_type empirical _exptl_absorpt_correction_T_min 0.969 _exptl_absorpt_correction_T_max 0.976 _exptl_absorpt_process_details 'Bruker SADABS' _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 'CCD area detector' _diffrn_measurement_method 'phi and omega scans' _diffrn_detector_area_resol_mean 8.366 _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 14831 _diffrn_reflns_av_R_equivalents 0.0633 _diffrn_reflns_av_sigmaI/netI 0.0834 _diffrn_reflns_limit_h_min -9 _diffrn_reflns_limit_h_max 9 _diffrn_reflns_limit_k_min -15 _diffrn_reflns_limit_k_max 15 _diffrn_reflns_limit_l_min -22 _diffrn_reflns_limit_l_max 22 _diffrn_reflns_theta_min 3.01 _diffrn_reflns_theta_max 27.48 _reflns_number_total 6511 _reflns_number_gt 3674 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SMART' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0656P)^2^+0.0277P] 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 6511 _refine_ls_number_parameters 416 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.1177 _refine_ls_R_factor_gt 0.0616 _refine_ls_wR_factor_ref 0.1671 _refine_ls_wR_factor_gt 0.1385 _refine_ls_goodness_of_fit_ref 1.032 _refine_ls_restrained_S_all 1.032 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group C1 C 0.4188(4) 0.3197(2) 0.32498(17) 0.0453(7) Uani 1 1 d . . . O1 O 0.4020(3) 0.25954(18) 0.37464(13) 0.0740(7) Uani 1 1 d . . . O2 O 0.3309(3) 0.29186(16) 0.25386(11) 0.0587(5) Uani 1 1 d . . . C2 C 0.5646(3) 0.4411(2) 0.35684(15) 0.0379(6) Uani 1 1 d . . . C3 C 0.6644(4) 0.4775(2) 0.43678(15) 0.0442(6) Uani 1 1 d . . . H3A H 0.6417 0.4287 0.4705 0.053 Uiso 1 1 calc R . . C4 C 0.7978(4) 0.5874(2) 0.46510(15) 0.0424(6) Uani 1 1 d . . . C5 C 0.8375(3) 0.6621(2) 0.41701(15) 0.0444(6) Uani 1 1 d . . . H5A H 0.9289 0.7349 0.4368 0.053 Uiso 1 1 calc R . . C6 C 0.7366(4) 0.6248(2) 0.33864(15) 0.0403(6) Uani 1 1 d . . . C7 C 0.6015(3) 0.5153(2) 0.30724(15) 0.0399(6) Uani 1 1 d . . . H7A H 0.5367 0.4920 0.2539 0.048 Uiso 1 1 calc R . . N1 N 0.9048(4) 0.6248(2) 0.54898(15) 0.0630(7) Uani 1 1 d . . . O3 O 1.0156(4) 0.7240(2) 0.57372(14) 0.1068(10) Uani 1 1 d . . . O4 O 0.8785(3) 0.5555(2) 0.58959(13) 0.0823(7) Uani 1 1 d . . . N2 N 0.7754(4) 0.7041(2) 0.28647(15) 0.0542(6) Uani 1 1 d . . . O5 O 0.8976(3) 0.79856(19) 0.31507(14) 0.0796(7) Uani 1 1 d . . . O6 O 0.6817(4) 0.6725(2) 0.21757(14) 0.0902(8) Uani 1 1 d . . . C8 C -0.0415(3) 0.1933(2) -0.02807(15) 0.0352(6) Uani 1 1 d . . . C9 C 0.0662(3) 0.32356(19) 0.01693(14) 0.0335(5) Uani 1 1 d . . . C10 C 0.0562(3) 0.3689(2) 0.09554(14) 0.0376(6) Uani 1 1 d . . . H10A H -0.0099 0.3198 0.1210 0.045 Uiso 1 1 calc R . . C11 C 0.1464(3) 0.4884(2) 0.13521(14) 0.0392(6) Uani 1 1 d . . . C12 C 0.2497(3) 0.5652(2) 0.10111(16) 0.0429(6) Uani 1 1 d . . . H12A H 0.3106 0.6447 0.1289 0.051 Uiso 1 1 calc R . . C13 C 0.2574(3) 0.5167(2) 0.02312(15) 0.0372(6) Uani 1 1 d . . . C14 C 0.1661(3) 0.3981(2) -0.02013(14) 0.0357(6) Uani 1 1 d . . . H14A H 0.1719 0.3695 -0.0729 0.043 Uiso 1 1 calc R . . O7 O -0.0898(2) 0.12561(14) 0.01445(10) 0.0444(4) Uani 1 1 d . . . O8 O -0.0762(3) 0.16538(15) -0.10228(10) 0.0506(5) Uani 1 1 d . . . O9 O 0.2208(4) 0.6372(2) 0.25409(14) 0.1077(10) Uani 1 1 d . . . O10 O 0.0025(4) 0.4781(2) 0.24011(13) 0.0826(7) Uani 1 1 d . . . N3 N 0.1224(4) 0.5382(2) 0.21613(14) 0.0572(6) Uani 1 1 d . . . N4 N 0.3622(3) 0.5964(2) -0.01656(16) 0.0488(6) Uani 1 1 d . . . O11 O 0.4472(3) 0.69897(17) 0.02339(14) 0.0789(7) Uani 1 1 d . . . O12 O 0.3618(3) 0.55644(19) -0.08643(14) 0.0678(6) Uani 1 1 d . . . N5 N 0.7390(3) -0.0678(2) 0.48526(13) 0.0481(6) Uani 1 1 d . . . C15 C 0.5683(4) -0.1433(2) 0.46410(15) 0.0450(6) Uani 1 1 d . . . H15A H 0.5446 -0.2000 0.4926 0.054 Uiso 1 1 calc R . . C16 C 0.4239(4) -0.1430(2) 0.40257(15) 0.0419(6) Uani 1 1 d . . . H16A H 0.3078 -0.1987 0.3903 0.050 Uiso 1 1 calc R . . C17 C 0.4539(3) -0.0585(2) 0.35914(14) 0.0375(6) Uani 1 1 d . . . C18 C 0.6323(3) 0.0193(2) 0.37966(15) 0.0441(6) Uani 1 1 d . . . H18A H 0.6599 0.0767 0.3521 0.053 Uiso 1 1 calc R . . C19 C 0.7692(4) 0.0110(2) 0.44153(16) 0.0473(7) Uani 1 1 d . . . H19A H 0.8887 0.0629 0.4535 0.057 Uiso 1 1 calc R . . C20 C 0.2965(4) -0.0498(2) 0.29523(15) 0.0490(7) Uani 1 1 d . . . H20A H 0.3493 -0.0210 0.2547 0.059 Uiso 1 1 calc R . . H20B H 0.2126 -0.1292 0.2699 0.059 Uiso 1 1 calc R . . N6 N 0.1870(3) 0.03424(17) 0.32977(12) 0.0413(5) Uani 1 1 d . . . H6A H 0.0951 0.0383 0.2912 0.062 Uiso 1 1 calc R . . H6B H 0.2637 0.1073 0.3524 0.062 Uiso 1 1 calc R . . H6C H 0.1368 0.0071 0.3663 0.062 Uiso 1 1 calc R . . N7 N 0.8651(3) 0.05395(19) 0.21731(12) 0.0444(5) Uani 1 1 d . . . C21 C 0.7237(4) -0.0353(2) 0.16739(16) 0.0473(7) Uani 1 1 d . . . H21A H 0.7350 -0.1142 0.1609 0.057 Uiso 1 1 calc R . . C22 C 0.5622(3) -0.0161(2) 0.12514(15) 0.0425(6) Uani 1 1 d . . . H22A H 0.4678 -0.0810 0.0912 0.051 Uiso 1 1 calc R . . C23 C 0.5412(3) 0.1009(2) 0.13355(13) 0.0340(5) Uani 1 1 d . . . C24 C 0.6874(3) 0.1937(2) 0.18484(14) 0.0393(6) Uani 1 1 d . . . H24A H 0.6800 0.2735 0.1922 0.047 Uiso 1 1 calc R . . C25 C 0.8443(3) 0.1664(2) 0.22495(15) 0.0424(6) Uani 1 1 d . . . H25A H 0.9410 0.2297 0.2592 0.051 Uiso 1 1 calc R . . C26 C 0.3663(3) 0.1250(2) 0.08805(14) 0.0376(6) Uani 1 1 d . . . H26A H 0.3909 0.2096 0.0889 0.045 Uiso 1 1 calc R . . H26B H 0.3370 0.0778 0.0328 0.045 Uiso 1 1 calc R . . N8 N 0.2001(2) 0.09393(16) 0.12264(11) 0.0341(5) Uani 1 1 d . . . H8A H 0.0997 0.1091 0.0944 0.051 Uiso 1 1 calc R . . H8B H 0.2255 0.1382 0.1730 0.051 Uiso 1 1 calc R . . H8C H 0.1758 0.0160 0.1211 0.051 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 C1 0.0411(15) 0.0352(14) 0.0496(17) 0.0027(13) 0.0041(13) 0.0031(12) O1 0.0800(15) 0.0447(12) 0.0781(16) 0.0253(11) -0.0083(12) -0.0136(10) O2 0.0561(12) 0.0515(11) 0.0460(12) -0.0063(9) 0.0035(10) -0.0082(9) C2 0.0388(13) 0.0292(12) 0.0396(14) 0.0050(11) 0.0044(11) 0.0042(10) C3 0.0469(15) 0.0381(14) 0.0438(16) 0.0117(12) 0.0045(12) 0.0069(12) C4 0.0458(15) 0.0372(14) 0.0361(14) 0.0044(11) 0.0012(12) 0.0055(11) C5 0.0377(14) 0.0368(13) 0.0481(16) 0.0014(12) 0.0057(12) 0.0009(11) C6 0.0453(15) 0.0319(13) 0.0422(15) 0.0085(11) 0.0128(12) 0.0058(11) C7 0.0447(14) 0.0357(13) 0.0328(14) 0.0022(11) 0.0047(11) 0.0070(11) N1 0.0665(17) 0.0595(17) 0.0469(16) 0.0087(13) -0.0060(13) 0.0035(14) O3 0.115(2) 0.0871(18) 0.0620(16) 0.0065(13) -0.0289(14) -0.0419(16) O4 0.1051(19) 0.0777(16) 0.0506(14) 0.0254(12) -0.0106(13) 0.0092(14) N2 0.0665(16) 0.0432(13) 0.0530(16) 0.0162(12) 0.0172(13) 0.0074(12) O5 0.0915(17) 0.0532(13) 0.0838(17) 0.0234(12) 0.0223(13) -0.0133(12) O6 0.126(2) 0.0746(16) 0.0541(15) 0.0283(13) 0.0017(14) -0.0063(15) C8 0.0295(12) 0.0324(13) 0.0377(14) 0.0055(11) -0.0031(10) 0.0089(10) C9 0.0324(12) 0.0295(12) 0.0348(13) 0.0063(10) 0.0007(10) 0.0085(10) C10 0.0388(13) 0.0364(13) 0.0376(14) 0.0124(11) 0.0033(11) 0.0118(11) C11 0.0453(14) 0.0368(13) 0.0312(13) 0.0042(11) 0.0002(11) 0.0144(11) C12 0.0382(14) 0.0303(13) 0.0512(17) 0.0030(12) -0.0027(12) 0.0095(11) C13 0.0308(12) 0.0321(12) 0.0489(16) 0.0131(12) 0.0063(11) 0.0086(10) C14 0.0337(13) 0.0364(13) 0.0350(13) 0.0067(11) 0.0027(10) 0.0128(10) O7 0.0485(10) 0.0338(9) 0.0437(10) 0.0122(8) -0.0010(8) 0.0022(8) O8 0.0628(12) 0.0430(10) 0.0328(10) 0.0032(8) 0.0005(9) 0.0012(9) O9 0.157(3) 0.0628(15) 0.0666(17) -0.0258(13) 0.0272(16) -0.0092(16) O10 0.112(2) 0.0803(17) 0.0566(15) 0.0100(12) 0.0381(14) 0.0194(15) N3 0.0742(18) 0.0487(15) 0.0413(14) -0.0012(12) 0.0056(13) 0.0210(13) N4 0.0369(12) 0.0404(13) 0.0723(18) 0.0185(13) 0.0131(12) 0.0127(10) O11 0.0870(16) 0.0376(11) 0.1060(19) 0.0112(12) 0.0390(14) -0.0044(11) O12 0.0770(15) 0.0644(14) 0.0662(15) 0.0239(12) 0.0281(12) 0.0096(11) N5 0.0432(13) 0.0540(14) 0.0465(14) 0.0132(11) 0.0035(10) 0.0179(11) C15 0.0548(17) 0.0392(14) 0.0417(16) 0.0132(12) 0.0072(13) 0.0147(13) C16 0.0405(14) 0.0403(14) 0.0400(15) 0.0064(12) 0.0073(12) 0.0060(11) C17 0.0385(14) 0.0430(14) 0.0281(13) 0.0056(11) 0.0037(10) 0.0120(11) C18 0.0429(15) 0.0514(16) 0.0426(16) 0.0185(13) 0.0140(12) 0.0120(13) C19 0.0327(14) 0.0560(17) 0.0509(17) 0.0128(14) 0.0071(12) 0.0100(12) C20 0.0488(16) 0.0584(17) 0.0359(15) 0.0114(13) 0.0007(12) 0.0146(14) N6 0.0353(11) 0.0370(11) 0.0452(13) 0.0153(10) -0.0030(9) 0.0010(9) N7 0.0341(11) 0.0517(14) 0.0462(13) 0.0147(11) 0.0059(10) 0.0095(10) C21 0.0442(15) 0.0378(14) 0.0595(18) 0.0111(13) 0.0101(13) 0.0132(12) C22 0.0364(14) 0.0341(13) 0.0487(16) 0.0048(12) 0.0040(12) 0.0023(11) C23 0.0315(12) 0.0393(13) 0.0313(13) 0.0125(11) 0.0078(10) 0.0054(10) C24 0.0383(13) 0.0322(12) 0.0434(15) 0.0090(11) 0.0068(11) 0.0038(11) C25 0.0329(13) 0.0454(15) 0.0399(15) 0.0063(12) 0.0022(11) 0.0009(11) C26 0.0342(13) 0.0437(14) 0.0343(14) 0.0153(11) 0.0040(10) 0.0065(11) N8 0.0311(10) 0.0329(10) 0.0326(11) 0.0060(8) 0.0010(8) 0.0044(8) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag C1 O2 1.245(3) 1 ? C1 O2 1.245(3) . ? C1 O1 1.254(3) . ? C1 O1 1.254(3) 1 ? C1 C2 1.527(3) . ? C2 C7 1.394(3) . ? C2 C3 1.398(3) . ? C3 C4 1.388(3) . ? C3 H3A 0.9300 . ? C4 C5 1.381(3) . ? C4 N1 1.472(3) . ? C5 C6 1.377(3) . ? C5 H5A 0.9300 . ? C6 C7 1.392(3) . ? C6 N2 1.477(3) . ? C7 H7A 0.9300 . ? N1 O4 1.212(3) . ? N1 O3 1.221(3) . ? N2 O6 1.222(3) . ? N2 O5 1.223(3) . ? C8 O8 1.244(3) . ? C8 O7 1.258(3) 1 ? C8 O7 1.258(3) . ? C8 C9 1.534(3) . ? C9 C14 1.389(3) . ? C9 C10 1.394(3) . ? C10 C11 1.388(3) . ? C10 H10A 0.9300 . ? C11 C12 1.381(4) . ? C11 N3 1.477(3) . ? C12 C13 1.386(3) . ? C12 H12A 0.9300 . ? C13 C14 1.395(3) . ? C13 N4 1.478(3) . ? C14 H14A 0.9300 . ? O9 N3 1.214(3) . ? O10 N3 1.224(3) . ? N4 O12 1.219(3) . ? N4 O11 1.227(3) . ? N5 C15 1.331(3) . ? N5 C19 1.345(3) . ? C15 C16 1.383(3) . ? C15 H15A 0.9300 . ? C16 C17 1.394(3) . ? C16 H16A 0.9300 . ? C17 C18 1.387(3) . ? C17 C20 1.507(3) . ? C18 C19 1.386(3) . ? C18 H18A 0.9300 . ? C19 H19A 0.9300 . ? C20 N6 1.494(3) . ? C20 H20A 0.9700 . ? C20 H20B 0.9700 . ? N6 H6A 0.8900 . ? N6 H6B 0.8900 . ? N6 H6C 0.8900 . ? N7 C25 1.338(3) . ? N7 C21 1.340(3) . ? C21 C22 1.379(3) . ? C21 H21A 0.9300 . ? C22 C23 1.390(3) . ? C22 H22A 0.9300 . ? C23 C24 1.387(3) . ? C23 C26 1.509(3) . ? C24 C25 1.382(3) . ? C24 H24A 0.9300 . ? C25 H25A 0.9300 . ? C26 N8 1.494(3) . ? C26 H26A 0.9700 . ? C26 H26B 0.9700 . ? N8 H8A 0.8900 . ? N8 H8B 0.8900 . ? N8 H8C 0.8900 . ? 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 C1 O1 127.5(2) 1 . ? O2 C1 O1 127.5(2) . . ? O2 C1 O1 127.5(2) 1 1 ? O2 C1 O1 127.5(2) . 1 ? O2 C1 C2 117.3(2) 1 . ? O2 C1 C2 117.3(2) . . ? O1 C1 C2 115.2(2) . . ? O1 C1 C2 115.2(2) 1 . ? C7 C2 C3 119.6(2) . . ? C7 C2 C1 121.0(2) . . ? C3 C2 C1 119.4(2) . . ? C4 C3 C2 119.1(2) . . ? C4 C3 H3A 120.5 . . ? C2 C3 H3A 120.5 . . ? C5 C4 C3 122.4(2) . . ? C5 C4 N1 118.5(2) . . ? C3 C4 N1 119.0(2) . . ? C6 C5 C4 117.4(2) . . ? C6 C5 H5A 121.3 . . ? C4 C5 H5A 121.3 . . ? C5 C6 C7 122.4(2) . . ? C5 C6 N2 118.3(2) . . ? C7 C6 N2 119.3(2) . . ? C6 C7 C2 119.1(2) . . ? C6 C7 H7A 120.4 . . ? C2 C7 H7A 120.4 . . ? O4 N1 O3 123.6(3) . . ? O4 N1 C4 118.3(2) . . ? O3 N1 C4 118.1(3) . . ? O6 N2 O5 123.7(2) . . ? O6 N2 C6 118.2(2) . . ? O5 N2 C6 118.1(2) . . ? O8 C8 O7 126.4(2) . 1 ? O8 C8 O7 126.4(2) . . ? O8 C8 C9 117.6(2) . . ? O7 C8 C9 116.0(2) 1 . ? O7 C8 C9 116.0(2) . . ? C14 C9 C10 119.6(2) . . ? C14 C9 C8 121.3(2) . . ? C10 C9 C8 119.0(2) . . ? C11 C10 C9 119.1(2) . . ? C11 C10 H10A 120.4 . . ? C9 C10 H10A 120.4 . . ? C12 C11 C10 123.2(2) . . ? C12 C11 N3 118.1(2) . . ? C10 C11 N3 118.6(2) . . ? C11 C12 C13 116.1(2) . . ? C11 C12 H12A 122.0 . . ? C13 C12 H12A 122.0 . . ? C12 C13 C14 123.1(2) . . ? C12 C13 N4 118.0(2) . . ? C14 C13 N4 118.8(2) . . ? C9 C14 C13 118.8(2) . . ? C9 C14 H14A 120.6 . . ? C13 C14 H14A 120.6 . . ? O9 N3 O10 124.2(3) . . ? O9 N3 C11 117.8(3) . . ? O10 N3 C11 118.0(2) . . ? O12 N4 O11 123.8(2) . . ? O12 N4 C13 118.5(2) . . ? O11 N4 C13 117.7(2) . . ? C15 N5 C19 116.1(2) . . ? N5 C15 C16 124.3(2) . . ? N5 C15 H15A 117.9 . . ? C16 C15 H15A 117.9 . . ? C15 C16 C17 119.4(2) . . ? C15 C16 H16A 120.3 . . ? C17 C16 H16A 120.3 . . ? C18 C17 C16 116.9(2) . . ? C18 C17 C20 122.0(2) . . ? C16 C17 C20 121.1(2) . . ? C19 C18 C17 119.6(2) . . ? C19 C18 H18A 120.2 . . ? C17 C18 H18A 120.2 . . ? N5 C19 C18 123.7(2) . . ? N5 C19 H19A 118.1 . . ? C18 C19 H19A 118.1 . . ? N6 C20 C17 110.8(2) . . ? N6 C20 H20A 109.5 . . ? C17 C20 H20A 109.5 . . ? N6 C20 H20B 109.5 . . ? C17 C20 H20B 109.5 . . ? H20A C20 H20B 108.1 . . ? C20 N6 H6A 109.5 . . ? C20 N6 H6B 109.5 . . ? H6A N6 H6B 109.5 . . ? C20 N6 H6C 109.5 . . ? H6A N6 H6C 109.5 . . ? H6B N6 H6C 109.5 . . ? C25 N7 C21 116.7(2) . . ? N7 C21 C22 123.4(2) . . ? N7 C21 H21A 118.3 . . ? C22 C21 H21A 118.3 . . ? C21 C22 C23 119.7(2) . . ? C21 C22 H22A 120.2 . . ? C23 C22 H22A 120.2 . . ? C24 C23 C22 117.3(2) . . ? C24 C23 C26 121.7(2) . . ? C22 C23 C26 121.0(2) . . ? C25 C24 C23 119.3(2) . . ? C25 C24 H24A 120.4 . . ? C23 C24 H24A 120.4 . . ? N7 C25 C24 123.7(2) . . ? N7 C25 H25A 118.1 . . ? C24 C25 H25A 118.1 . . ? N8 C26 C23 111.90(18) . . ? N8 C26 H26A 109.2 . . ? C23 C26 H26A 109.2 . . ? N8 C26 H26B 109.2 . . ? C23 C26 H26B 109.2 . . ? H26A C26 H26B 107.9 . . ? C26 N8 H8A 109.5 . . ? C26 N8 H8B 109.5 . . ? H8A N8 H8B 109.5 . . ? C26 N8 H8C 109.5 . . ? H8A N8 H8C 109.5 . . ? H8B N8 H8C 109.5 . . ? 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 N6 H6A N7 0.89 2.02 2.900(3) 171.0 1_455 N6 H6B O1 0.89 1.80 2.668(3) 166.2 1 N6 H6C O5 0.89 2.59 3.080(3) 115.9 1_445 N6 H6C N5 0.89 2.51 3.139(3) 128.6 2_656 N8 H8C O7 0.89 2.48 2.973(3) 115.2 2 N8 H8C O8 0.89 2.04 2.921(3) 169.4 2 N8 H8A O7 0.89 1.88 2.750(3) 166.5 1 N8 H8B O2 0.89 1.95 2.757(3) 150.5 1 C15 H15A O1 0.93 2.58 3.419(4) 149.8 2_656 C22 H22A O11 0.93 2.55 3.282(3) 135.6 1_545 C26 H26B O7 0.97 2.57 3.168(3) 120.1 2 _diffrn_measured_fraction_theta_max 0.990 _diffrn_reflns_theta_full 27.48 _diffrn_measured_fraction_theta_full 0.990 _refine_diff_density_max 0.191 _refine_diff_density_min -0.295 _refine_diff_density_rms 0.052