# Electronic Supplementary Material (ESI) for Dalton Transactions # This journal is © The Royal Society of Chemistry 2011 data_global _journal_coden_Cambridge 222 loop_ _publ_author_name 'Mazzanti, M.' _publ_contact_author_name 'Mazzanti, M.' _publ_contact_author_email marinella.mazzanti@cea.fr _publ_section_title ; Self-assembly of highly luminescent lanthanide complexes promoted by pyridine-tetrazolate ligands ; # Attachment '- Eupytz.cif' data_ea107 _database_code_depnum_ccdc_archive 'CCDC 842473' #TrackingRef '- Eupytz.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C58 H82 Eu2 K6 N54 O16' _chemical_formula_weight 2330.30 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' K K 0.2009 0.2494 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Eu Eu -0.1578 3.6682 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M 'C 2/c' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y, -z+1/2' 'x+1/2, y+1/2, z' '-x+1/2, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y, z-1/2' '-x+1/2, -y+1/2, -z' 'x+1/2, -y+1/2, z-1/2' _cell_length_a 19.2814(7) _cell_length_b 10.7776(3) _cell_length_c 26.07570(10) _cell_angle_alpha 90.00 _cell_angle_beta 119.752(2) _cell_angle_gamma 90.00 _cell_volume 4704.4(2) _cell_formula_units_Z 2 _cell_measurement_temperature 150(2) _cell_measurement_reflns_used 13554 _cell_measurement_theta_min 3.0099 _cell_measurement_theta_max 28.9358 _exptl_crystal_description bloc _exptl_crystal_colour colourless _exptl_crystal_size_max 0.49 _exptl_crystal_size_mid 0.36 _exptl_crystal_size_min 0.23 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.645 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 2352 _exptl_absorpt_coefficient_mu 1.675 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.4923 _exptl_absorpt_correction_T_max 0.6983 _exptl_absorpt_process_details ; CrysAlis RED, Oxford Diffraction Ltd., Version 1.171.32.15 (release 10-01-2008 CrysAlis171 .NET) (compiled Jan 10 2008,16:37:18) Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm. ; _exptl_special_details ; ? ; _diffrn_ambient_temperature 150(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type ? _diffrn_measurement_method ? _diffrn_detector_area_resol_mean 15.9653 _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 22598 _diffrn_reflns_av_R_equivalents 0.0260 _diffrn_reflns_av_sigmaI/netI 0.0256 _diffrn_reflns_limit_h_min -25 _diffrn_reflns_limit_h_max 24 _diffrn_reflns_limit_k_min -14 _diffrn_reflns_limit_k_max 14 _diffrn_reflns_limit_l_min -34 _diffrn_reflns_limit_l_max 34 _diffrn_reflns_theta_min 3.01 _diffrn_reflns_theta_max 28.28 _reflns_number_total 5622 _reflns_number_gt 5208 _reflns_threshold_expression >2sigma(I) _computing_data_collection ; CrysAlis CCD, Oxford Diffraction Ltd., Version 1.171.32.15 (release 10-01-2008 CrysAlis171 .NET) (compiled Jan 10 2008,16:37:18) ; _diffrn_measurement_details ; #__ type_ start__ end____ width___ exp.time_ 1 omega -54.00 42.00 1.0000 2.5000 omega____ theta____ kappa____ phi______ omega'___ theta'___ frames - 17.3113 -42.0000 49.0000 0.0000 0.0000 96 #__ type_ start__ end____ width___ exp.time_ 2 omega 4.00 54.00 1.0000 2.5000 omega____ theta____ kappa____ phi______ omega'___ theta'___ frames - -18.8738 0.0000 240.0000 0.0000 0.0000 50 #__ type_ start__ end____ width___ exp.time_ 3 omega -92.00 8.00 1.0000 2.5000 omega____ theta____ kappa____ phi______ omega'___ theta'___ frames - -18.8738 0.0000 30.0000 0.0000 0.0000 100 #__ type_ start__ end____ width___ exp.time_ 4 omega -89.00 -38.00 1.0000 2.5000 omega____ theta____ kappa____ phi______ omega'___ theta'___ frames - -18.8738 -77.0000 210.0000 0.0000 0.0000 51 #__ type_ start__ end____ width___ exp.time_ 5 omega 0.00 51.00 1.0000 2.5000 omega____ theta____ kappa____ phi______ omega'___ theta'___ frames - -18.8738 77.0000 120.0000 0.0000 0.0000 51 #__ type_ start__ end____ width___ exp.time_ 6 omega -88.00 -40.00 1.0000 2.5000 omega____ theta____ kappa____ phi______ omega'___ theta'___ frames - -18.8738 -45.0000 120.0000 0.0000 0.0000 48 #__ type_ start__ end____ width___ exp.time_ 7 omega -32.00 -5.00 1.0000 2.5000 omega____ theta____ kappa____ phi______ omega'___ theta'___ frames - -18.8738 45.0000 150.0000 0.0000 0.0000 27 #__ type_ start__ end____ width___ exp.time_ 8 omega -38.00 7.00 1.0000 2.5000 omega____ theta____ kappa____ phi______ omega'___ theta'___ frames - -18.8738 45.0000 30.0000 0.0000 0.0000 45 ; _computing_cell_refinement ; CrysAlis RED, Oxford Diffraction Ltd., Version 1.171.32.15 (release 10-01-2008 CrysAlis171 .NET) (compiled Jan 10 2008,16:37:18) ; _computing_data_reduction ; CrysAlis RED, Oxford Diffraction Ltd., Version 1.171.32.15 (release 10-01-2008 CrysAlis171 .NET) (compiled Jan 10 2008,16:37:18) ; _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^)+(0.0267P)^2^+3.5730P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens difmap _refine_ls_hydrogen_treatment refall _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 5622 _refine_ls_number_parameters 392 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0255 _refine_ls_R_factor_gt 0.0223 _refine_ls_wR_factor_ref 0.0538 _refine_ls_wR_factor_gt 0.0532 _refine_ls_goodness_of_fit_ref 1.081 _refine_ls_restrained_S_all 1.081 _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 Eu1 Eu 0.5000 0.529331(12) 0.7500 0.01499(5) Uani 1 2 d S . . K1 K 0.80991(3) 0.65746(4) 0.96689(2) 0.02685(10) Uani 1 1 d . . . K2 K 1.0000 0.5000 1.0000 0.02994(15) Uani 1 2 d S . . N1 N 0.45970(10) 0.45444(15) 0.82256(7) 0.0204(3) Uani 1 1 d . . . N2 N 0.47815(11) 0.35401(16) 0.85708(8) 0.0259(4) Uani 1 1 d . . . N3 N 0.43209(11) 0.35181(16) 0.88089(8) 0.0254(4) Uani 1 1 d . . . N4 N 0.38223(11) 0.44985(16) 0.86289(8) 0.0234(4) Uani 1 1 d . . . N5 N 0.38375(9) 0.64886(14) 0.75212(7) 0.0166(3) Uani 1 1 d . . . N6 N 0.43684(10) 0.70394(15) 0.67603(7) 0.0195(3) Uani 1 1 d . . . N7 N 0.44191(11) 0.74208(16) 0.62883(8) 0.0258(4) Uani 1 1 d . . . N8 N 0.38328(12) 0.81908(17) 0.59795(8) 0.0292(4) Uani 1 1 d . . . N9 N 0.33850(11) 0.83442(16) 0.62417(8) 0.0262(4) Uani 1 1 d . . . C1 C 0.40115(11) 0.51079(17) 0.82720(8) 0.0177(4) Uani 1 1 d . . . C2 C 0.36117(11) 0.62012(17) 0.79174(8) 0.0181(4) Uani 1 1 d . . . C3 C 0.30269(13) 0.6860(2) 0.79645(10) 0.0249(4) Uani 1 1 d . . . H3 H 0.2903(15) 0.661(2) 0.8246(11) 0.031(6) Uiso 1 1 d . . . C4 C 0.26640(13) 0.7837(2) 0.75826(10) 0.0289(5) Uani 1 1 d . . . H4 H 0.2332(16) 0.824(2) 0.7619(11) 0.031(7) Uiso 1 1 d . . . C5 C 0.28741(13) 0.8126(2) 0.71633(10) 0.0249(4) Uani 1 1 d . . . H5 H 0.2639(15) 0.877(2) 0.6901(10) 0.030(6) Uiso 1 1 d . . . C6 C 0.34668(11) 0.74300(17) 0.71468(8) 0.0186(4) Uani 1 1 d . . . C7 C 0.37308(11) 0.76235(17) 0.67165(8) 0.0184(4) Uani 1 1 d . . . N11 N 0.62766(9) 0.42759(15) 0.82599(7) 0.0195(3) Uani 1 1 d . . . N12 N 0.69875(10) 0.46675(16) 0.86914(8) 0.0251(4) Uani 1 1 d . . . N13 N 0.74368(10) 0.36931(17) 0.89448(8) 0.0263(4) Uani 1 1 d . . . N14 N 0.70391(10) 0.26417(16) 0.86941(7) 0.0235(4) Uani 1 1 d . . . N15 N 0.5000 0.2897(2) 0.7500 0.0173(4) Uani 1 2 d S . . C11 C 0.63274(11) 0.30349(18) 0.82766(8) 0.0183(4) Uani 1 1 d . . . C12 C 0.56534(12) 0.22590(18) 0.78754(8) 0.0194(4) Uani 1 1 d . . . C13 C 0.56816(14) 0.0981(2) 0.78886(10) 0.0275(5) Uani 1 1 d . . . H13 H 0.6133(15) 0.063(2) 0.8138(11) 0.027(6) Uiso 1 1 d . . . C14 C 0.5000 0.0337(3) 0.7500 0.0333(7) Uani 1 2 d S . . H14 H 0.5000 -0.043(4) 0.7500 0.059(14) Uiso 1 2 d S . . O1 O 0.71009(11) 0.59496(16) 1.01186(9) 0.0335(4) Uani 1 1 d . . . H1O H 0.735(2) 0.584(3) 1.0412(14) 0.056(12) Uiso 1 1 d . . . C21 C 0.6512(2) 0.5018(3) 0.99160(19) 0.0558(8) Uani 1 1 d . . . H21A H 0.676(2) 0.422(4) 1.0020(17) 0.088(13) Uiso 1 1 d . . . H21B H 0.6176(18) 0.520(2) 0.9509(13) 0.037(8) Uiso 1 1 d . . . H21C H 0.615(3) 0.507(4) 1.0075(19) 0.095(14) Uiso 1 1 d . . . O2 O 0.98446(11) 0.72407(17) 1.03971(8) 0.0403(4) Uani 1 1 d . . . H2O H 0.9829(19) 0.736(3) 1.0697(14) 0.054(9) Uiso 1 1 d . . . C22 C 1.03636(17) 0.8102(3) 1.03502(12) 0.0369(6) Uani 1 1 d . . . H22A H 1.0315(19) 0.794(3) 0.9967(14) 0.060(9) Uiso 1 1 d . . . H22B H 1.0192(19) 0.887(3) 1.0378(13) 0.058(9) Uiso 1 1 d . . . H22C H 1.0927(18) 0.790(3) 1.0672(12) 0.048(8) Uiso 1 1 d . . . O3 O 1.12734(9) 0.57673(15) 0.99672(7) 0.0277(3) Uani 1 1 d . . . H3O H 1.1659(16) 0.602(2) 1.0298(12) 0.035(7) Uiso 1 1 d . . . C23 C 1.1306(2) 0.6350(3) 0.94928(13) 0.0409(6) Uani 1 1 d . . . H23A H 1.101(2) 0.720(4) 0.9397(16) 0.084(11) Uiso 1 1 d . . . H23B H 1.095(3) 0.590(5) 0.917(2) 0.15(2) Uiso 1 1 d . . . H23C H 1.184(3) 0.632(5) 0.945(2) 0.15(2) Uiso 1 1 d . . . O4 O 1.11145(10) 0.37834(15) 1.09644(7) 0.0330(4) Uani 1 1 d . . . H4O H 1.0940(18) 0.303(3) 1.1013(13) 0.052(8) Uiso 1 1 d . . . C24 C 1.1294(2) 0.4504(3) 1.14718(14) 0.0483(7) Uani 1 1 d . . . H24A H 1.122(2) 0.536(3) 1.1356(16) 0.082(12) Uiso 1 1 d . . . H24B H 1.116(2) 0.414(4) 1.1740(16) 0.082(12) Uiso 1 1 d . . . H24C H 1.186(2) 0.442(3) 1.1766(16) 0.075(11) 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 Eu1 0.01467(7) 0.01398(7) 0.01575(7) 0.000 0.00711(5) 0.000 K1 0.0284(2) 0.0248(2) 0.0286(2) -0.00117(18) 0.0150(2) 0.00207(18) K2 0.0230(3) 0.0267(3) 0.0401(4) 0.0043(3) 0.0157(3) 0.0009(2) N1 0.0221(8) 0.0195(8) 0.0207(8) 0.0053(7) 0.0113(7) 0.0024(7) N2 0.0288(9) 0.0238(9) 0.0256(9) 0.0075(7) 0.0140(8) 0.0026(7) N3 0.0290(9) 0.0249(9) 0.0236(9) 0.0038(7) 0.0139(8) -0.0017(7) N4 0.0258(9) 0.0246(9) 0.0215(8) 0.0002(7) 0.0129(7) -0.0035(7) N5 0.0163(8) 0.0163(7) 0.0153(8) -0.0018(6) 0.0065(6) -0.0006(6) N6 0.0220(8) 0.0188(8) 0.0194(8) 0.0030(7) 0.0115(7) 0.0012(7) N7 0.0318(10) 0.0257(9) 0.0239(9) 0.0064(7) 0.0168(8) 0.0046(7) N8 0.0357(10) 0.0292(10) 0.0253(9) 0.0099(8) 0.0173(8) 0.0104(8) N9 0.0295(10) 0.0253(9) 0.0244(9) 0.0066(7) 0.0139(8) 0.0075(7) C1 0.0182(9) 0.0189(9) 0.0159(9) -0.0024(7) 0.0085(8) -0.0031(7) C2 0.0176(9) 0.0186(9) 0.0167(9) -0.0019(7) 0.0074(8) -0.0024(7) C3 0.0238(10) 0.0304(11) 0.0245(11) -0.0008(9) 0.0149(9) 0.0009(9) C4 0.0256(11) 0.0299(12) 0.0365(13) -0.0005(10) 0.0194(10) 0.0096(10) C5 0.0246(10) 0.0232(10) 0.0250(11) 0.0031(9) 0.0108(9) 0.0075(8) C6 0.0186(9) 0.0168(9) 0.0177(9) -0.0015(7) 0.0068(8) -0.0011(7) C7 0.0187(9) 0.0159(9) 0.0173(9) 0.0006(7) 0.0065(8) 0.0005(7) N11 0.0176(8) 0.0192(8) 0.0187(8) 0.0006(7) 0.0066(7) 0.0000(6) N12 0.0177(8) 0.0281(9) 0.0234(9) 0.0013(8) 0.0055(7) 0.0000(7) N13 0.0196(8) 0.0293(9) 0.0250(9) 0.0008(8) 0.0073(7) 0.0014(7) N14 0.0207(8) 0.0258(9) 0.0221(9) 0.0021(7) 0.0091(7) 0.0031(7) N15 0.0182(11) 0.0171(11) 0.0170(11) 0.000 0.0089(9) 0.000 C11 0.0186(9) 0.0204(9) 0.0182(9) 0.0028(8) 0.0109(8) 0.0037(7) C12 0.0216(10) 0.0195(9) 0.0180(9) 0.0007(8) 0.0106(8) 0.0013(8) C13 0.0288(11) 0.0201(10) 0.0273(11) 0.0034(9) 0.0093(10) 0.0057(9) C14 0.0393(18) 0.0161(15) 0.0359(18) 0.000 0.0122(15) 0.000 O1 0.0303(9) 0.0289(9) 0.0382(11) -0.0006(8) 0.0147(8) -0.0049(7) C21 0.0400(16) 0.0419(17) 0.079(3) -0.0064(16) 0.0245(18) -0.0145(13) O2 0.0528(11) 0.0408(10) 0.0424(10) -0.0128(8) 0.0351(10) -0.0137(8) C22 0.0427(15) 0.0369(14) 0.0356(14) -0.0082(11) 0.0228(12) -0.0104(12) O3 0.0247(8) 0.0308(8) 0.0240(8) 0.0011(7) 0.0093(7) -0.0039(7) C23 0.0607(18) 0.0321(13) 0.0357(14) 0.0104(11) 0.0283(14) 0.0085(13) O4 0.0453(10) 0.0264(8) 0.0307(9) 0.0033(7) 0.0216(8) -0.0051(7) C24 0.071(2) 0.0384(16) 0.0366(15) -0.0056(12) 0.0275(16) -0.0045(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 Eu1 N1 2.5089(16) 2_656 ? Eu1 N1 2.5090(16) . ? Eu1 N11 2.5193(16) . ? Eu1 N11 2.5193(16) 2_656 ? Eu1 N6 2.5325(16) . ? Eu1 N6 2.5326(16) 2_656 ? Eu1 N15 2.583(2) . ? Eu1 N5 2.6095(16) . ? Eu1 N5 2.6096(16) 2_656 ? K1 O3 2.7559(17) 5_767 ? K1 O4 2.7676(17) 5_767 ? K1 O1 2.7880(19) . ? K1 O1 2.7908(18) 7_667 ? K1 N8 2.9911(18) 8_566 ? K1 O2 3.017(2) . ? K1 N12 3.1454(18) . ? K1 N9 3.2743(19) 2_656 ? K1 K1 4.0323(9) 7_667 ? K1 H1O 3.05(3) . ? K2 O3 2.6321(15) . ? K2 O3 2.6322(15) 5_767 ? K2 O4 2.7014(16) 5_767 ? K2 O4 2.7014(17) . ? K2 O2 2.7021(18) 5_767 ? K2 O2 2.7022(18) . ? K2 C24 3.426(3) 5_767 ? K2 C22 3.445(3) 5_767 ? K2 K1 3.7306(5) 5_767 ? N1 N2 1.338(2) . ? N1 C1 1.339(3) . ? N2 N3 1.312(3) . ? N3 N4 1.347(2) . ? N4 C1 1.330(3) . ? N5 C2 1.341(2) . ? N5 C6 1.342(2) . ? N6 C7 1.335(2) . ? N6 N7 1.346(2) . ? N7 N8 1.308(2) . ? N8 N9 1.351(3) . ? N8 K1 2.9911(18) 8_465 ? N9 C7 1.327(2) . ? N9 K1 3.2742(19) 2_656 ? C1 C2 1.460(3) . ? C2 C3 1.389(3) . ? C3 C4 1.377(3) . ? C3 H3 0.92(3) . ? C4 C5 1.377(3) . ? C4 H4 0.82(3) . ? C5 C6 1.385(3) . ? C5 H5 0.92(2) . ? C6 C7 1.459(3) . ? N11 N12 1.339(2) . ? N11 C11 1.340(2) . ? N12 N13 1.312(2) . ? N13 N14 1.342(2) . ? N14 C11 1.329(2) . ? N15 C12 1.339(2) 2_656 ? N15 C12 1.339(2) . ? C11 C12 1.461(3) . ? C12 C13 1.379(3) . ? C13 C14 1.383(3) . ? C13 H13 0.87(3) . ? C14 C13 1.383(3) 2_656 ? C14 H14 0.82(4) . ? O1 C21 1.407(3) . ? O1 K1 2.7908(18) 7_667 ? O1 H1O 0.68(3) . ? C21 H21A 0.95(4) . ? C21 H21B 0.95(3) . ? C21 H21C 0.97(5) . ? O2 C22 1.414(3) . ? O2 H2O 0.81(3) . ? C22 H22A 0.97(3) . ? C22 H22B 0.91(3) . ? C22 H22C 1.01(3) . ? O3 C23 1.416(3) . ? O3 K1 2.7559(16) 5_767 ? O3 H3O 0.86(3) . ? C23 H23A 1.05(4) . ? C23 H23B 0.91(6) . ? C23 H23C 1.08(6) . ? O4 C24 1.421(3) . ? O4 K1 2.7676(17) 5_767 ? O4 H4O 0.91(3) . ? C24 H24A 0.96(4) . ? C24 H24B 0.94(4) . ? C24 H24C 0.98(4) . ? 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 N1 Eu1 N1 142.47(7) 2_656 . ? N1 Eu1 N11 84.59(5) 2_656 . ? N1 Eu1 N11 79.29(5) . . ? N1 Eu1 N11 79.29(5) 2_656 2_656 ? N1 Eu1 N11 84.59(5) . 2_656 ? N11 Eu1 N11 128.40(8) . 2_656 ? N1 Eu1 N6 82.91(5) 2_656 . ? N1 Eu1 N6 126.99(5) . . ? N11 Eu1 N6 146.65(5) . . ? N11 Eu1 N6 79.13(5) 2_656 . ? N1 Eu1 N6 126.99(5) 2_656 2_656 ? N1 Eu1 N6 82.91(5) . 2_656 ? N11 Eu1 N6 79.13(5) . 2_656 ? N11 Eu1 N6 146.65(5) 2_656 2_656 ? N6 Eu1 N6 84.01(7) . 2_656 ? N1 Eu1 N15 71.23(4) 2_656 . ? N1 Eu1 N15 71.23(4) . . ? N11 Eu1 N15 64.20(4) . . ? N11 Eu1 N15 64.20(4) 2_656 . ? N6 Eu1 N15 137.99(4) . . ? N6 Eu1 N15 137.99(4) 2_656 . ? N1 Eu1 N5 139.96(5) 2_656 . ? N1 Eu1 N5 63.39(5) . . ? N11 Eu1 N5 135.43(5) . . ? N11 Eu1 N5 73.58(5) 2_656 . ? N6 Eu1 N5 63.63(5) . . ? N6 Eu1 N5 73.17(5) 2_656 . ? N15 Eu1 N5 119.58(3) . . ? N1 Eu1 N5 63.39(5) 2_656 2_656 ? N1 Eu1 N5 139.96(5) . 2_656 ? N11 Eu1 N5 73.58(5) . 2_656 ? N11 Eu1 N5 135.43(5) 2_656 2_656 ? N6 Eu1 N5 73.17(5) . 2_656 ? N6 Eu1 N5 63.63(5) 2_656 2_656 ? N15 Eu1 N5 119.58(3) . 2_656 ? N5 Eu1 N5 120.84(7) . 2_656 ? O3 K1 O4 78.52(5) 5_767 5_767 ? O3 K1 O1 84.87(5) 5_767 . ? O4 K1 O1 156.09(5) 5_767 . ? O3 K1 O1 152.58(6) 5_767 7_667 ? O4 K1 O1 114.99(5) 5_767 7_667 ? O1 K1 O1 87.43(5) . 7_667 ? O3 K1 N8 78.82(5) 5_767 8_566 ? O4 K1 N8 127.24(5) 5_767 8_566 ? O1 K1 N8 64.76(6) . 8_566 ? O1 K1 N8 74.09(6) 7_667 8_566 ? O3 K1 O2 80.75(5) 5_767 . ? O4 K1 O2 68.81(5) 5_767 . ? O1 K1 O2 125.45(6) . . ? O1 K1 O2 82.44(5) 7_667 . ? N8 K1 O2 60.89(5) 8_566 . ? O3 K1 N12 71.74(5) 5_767 . ? O4 K1 N12 77.30(5) 5_767 . ? O1 K1 N12 81.25(5) . . ? O1 K1 N12 132.84(5) 7_667 . ? N8 K1 N12 136.62(5) 8_566 . ? O2 K1 N12 139.83(5) . . ? O3 K1 N9 149.26(5) 5_767 2_656 ? O4 K1 N9 100.89(5) 5_767 2_656 ? O1 K1 N9 84.74(5) . 2_656 ? O1 K1 N9 55.24(5) 7_667 2_656 ? N8 K1 N9 121.79(5) 8_566 2_656 ? O2 K1 N9 128.19(5) . 2_656 ? N12 K1 N9 78.12(4) . 2_656 ? O3 K1 K1 123.54(4) 5_767 7_667 ? O4 K1 K1 157.59(4) 5_767 7_667 ? O1 K1 K1 43.74(4) . 7_667 ? O1 K1 K1 43.69(4) 7_667 7_667 ? N8 K1 K1 61.02(4) 8_566 7_667 ? O2 K1 K1 108.06(4) . 7_667 ? N12 K1 K1 111.44(4) . 7_667 ? N9 K1 K1 62.74(3) 2_656 7_667 ? O3 K1 H1O 79.1(7) 5_767 . ? O4 K1 H1O 156.8(7) 5_767 . ? O1 K1 H1O 12.4(6) . . ? O1 K1 H1O 87.9(7) 7_667 . ? N8 K1 H1O 53.1(6) 8_566 . ? O2 K1 H1O 113.3(6) . . ? N12 K1 H1O 89.9(7) . . ? N9 K1 H1O 95.2(7) 2_656 . ? K1 K1 H1O 45.6(7) 7_667 . ? O3 K2 O3 180.0 . 5_767 ? O3 K2 O4 98.12(5) . 5_767 ? O3 K2 O4 81.88(5) 5_767 5_767 ? O3 K2 O4 81.88(5) . . ? O3 K2 O4 98.12(5) 5_767 . ? O4 K2 O4 179.997(1) 5_767 . ? O3 K2 O2 89.18(5) . 5_767 ? O3 K2 O2 90.82(5) 5_767 5_767 ? O4 K2 O2 105.39(6) 5_767 5_767 ? O4 K2 O2 74.61(5) . 5_767 ? O3 K2 O2 90.82(5) . . ? O3 K2 O2 89.18(5) 5_767 . ? O4 K2 O2 74.61(5) 5_767 . ? O4 K2 O2 105.38(5) . . ? O2 K2 O2 180.00(9) 5_767 . ? O3 K2 C24 95.00(7) . 5_767 ? O3 K2 C24 85.01(7) 5_767 5_767 ? O4 K2 C24 23.18(6) 5_767 5_767 ? O4 K2 C24 156.82(6) . 5_767 ? O2 K2 C24 82.40(7) 5_767 5_767 ? O2 K2 C24 97.60(7) . 5_767 ? O3 K2 C22 111.51(6) . 5_767 ? O3 K2 C22 68.49(6) 5_767 5_767 ? O4 K2 C22 105.13(6) 5_767 5_767 ? O4 K2 C22 74.87(6) . 5_767 ? O2 K2 C22 22.74(6) 5_767 5_767 ? O2 K2 C22 157.26(6) . 5_767 ? C24 K2 C22 85.14(7) 5_767 5_767 ? O3 K2 K1 47.57(4) . 5_767 ? O3 K2 K1 132.43(4) 5_767 5_767 ? O4 K2 K1 132.27(4) 5_767 5_767 ? O4 K2 K1 47.74(4) . 5_767 ? O2 K2 K1 53.07(4) 5_767 5_767 ? O2 K2 K1 126.93(4) . 5_767 ? C24 K2 K1 114.58(6) 5_767 5_767 ? C22 K2 K1 70.56(5) 5_767 5_767 ? N2 N1 C1 105.12(16) . . ? N2 N1 Eu1 133.55(13) . . ? C1 N1 Eu1 120.84(12) . . ? N3 N2 N1 108.44(17) . . ? N2 N3 N4 110.78(16) . . ? C1 N4 N3 103.60(16) . . ? C2 N5 C6 118.40(16) . . ? C2 N5 Eu1 120.85(12) . . ? C6 N5 Eu1 120.72(12) . . ? C7 N6 N7 105.04(16) . . ? C7 N6 Eu1 119.34(12) . . ? N7 N6 Eu1 134.23(12) . . ? N8 N7 N6 108.88(17) . . ? N7 N8 N9 109.89(16) . . ? N7 N8 K1 122.07(13) . 8_465 ? N9 N8 K1 120.60(13) . 8_465 ? C7 N9 N8 104.42(16) . . ? C7 N9 K1 100.91(12) . 2_656 ? N8 N9 K1 96.30(12) . 2_656 ? N4 C1 N1 112.06(17) . . ? N4 C1 C2 126.87(18) . . ? N1 C1 C2 120.86(17) . . ? N5 C2 C3 122.56(18) . . ? N5 C2 C1 113.76(17) . . ? C3 C2 C1 123.63(18) . . ? C4 C3 C2 118.1(2) . . ? C4 C3 H3 124.4(16) . . ? C2 C3 H3 117.6(16) . . ? C5 C4 C3 120.2(2) . . ? C5 C4 H4 121.8(18) . . ? C3 C4 H4 118.0(18) . . ? C4 C5 C6 118.3(2) . . ? C4 C5 H5 122.0(15) . . ? C6 C5 H5 119.6(15) . . ? N5 C6 C5 122.44(18) . . ? N5 C6 C7 113.85(17) . . ? C5 C6 C7 123.68(18) . . ? N9 C7 N6 111.76(17) . . ? N9 C7 C6 126.56(18) . . ? N6 C7 C6 121.67(17) . . ? N12 N11 C11 105.04(15) . . ? N12 N11 Eu1 135.82(13) . . ? C11 N11 Eu1 119.15(12) . . ? N13 N12 N11 108.40(16) . . ? N13 N12 K1 95.79(11) . . ? N11 N12 K1 152.72(13) . . ? N12 N13 N14 110.83(16) . . ? C11 N14 N13 103.76(16) . . ? C12 N15 C12 118.3(2) 2_656 . ? C12 N15 Eu1 120.87(12) 2_656 . ? C12 N15 Eu1 120.87(12) . . ? N14 C11 N11 111.97(17) . . ? N14 C11 C12 126.47(18) . . ? N11 C11 C12 121.56(17) . . ? N15 C12 C13 122.83(19) . . ? N15 C12 C11 114.18(17) . . ? C13 C12 C11 122.98(18) . . ? C12 C13 C14 118.2(2) . . ? C12 C13 H13 117.5(16) . . ? C14 C13 H13 124.3(16) . . ? C13 C14 C13 119.8(3) 2_656 . ? C13 C14 H14 120.11(14) 2_656 . ? C13 C14 H14 120.11(15) . . ? C21 O1 K1 127.7(2) . . ? C21 O1 K1 126.24(19) . 7_667 ? K1 O1 K1 92.57(5) . 7_667 ? C21 O1 H1O 107(3) . . ? K1 O1 H1O 106(3) . . ? K1 O1 H1O 91(3) 7_667 . ? O1 C21 H21A 110(2) . . ? O1 C21 H21B 104.5(17) . . ? H21A C21 H21B 118(3) . . ? O1 C21 H21C 115(3) . . ? H21A C21 H21C 107(3) . . ? H21B C21 H21C 103(3) . . ? C22 O2 K2 109.62(15) . . ? C22 O2 K1 135.89(17) . . ? K2 O2 K1 81.22(5) . . ? C22 O2 H2O 110(2) . . ? K2 O2 H2O 126(2) . . ? K1 O2 H2O 95(2) . . ? O2 C22 H22A 105.1(19) . . ? O2 C22 H22B 107(2) . . ? H22A C22 H22B 113(3) . . ? O2 C22 H22C 107.4(16) . . ? H22A C22 H22C 109(2) . . ? H22B C22 H22C 115(3) . . ? C23 O3 K2 127.89(17) . . ? C23 O3 K1 120.31(15) . 5_767 ? K2 O3 K1 87.61(5) . 5_767 ? C23 O3 H3O 110.1(18) . . ? K2 O3 H3O 115.1(18) . . ? K1 O3 H3O 86.3(17) 5_767 . ? O3 C23 H23A 110(2) . . ? O3 C23 H23B 104(4) . . ? H23A C23 H23B 100(4) . . ? O3 C23 H23C 122(3) . . ? H23A C23 H23C 116(3) . . ? H23B C23 H23C 102(4) . . ? C24 O4 K2 108.36(17) . . ? C24 O4 K1 132.81(18) . 5_767 ? K2 O4 K1 86.01(5) . 5_767 ? C24 O4 H4O 107.1(18) . . ? K2 O4 H4O 112.6(19) . . ? K1 O4 H4O 107.8(19) 5_767 . ? O4 C24 H24A 108(2) . . ? O4 C24 H24B 116(2) . . ? H24A C24 H24B 126(3) . . ? O4 C24 H24C 110(2) . . ? H24A C24 H24C 106(3) . . ? H24B C24 H24C 89(3) . . ? 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 O4 H4O N3 0.91(3) 1.86(3) 2.775(2) 174(3) 7_657 O3 H3O N13 0.86(3) 1.90(3) 2.751(2) 170(3) 5_767 O2 H2O N7 0.81(3) 2.06(3) 2.846(2) 162(3) 8_566 O1 H1O N9 0.68(3) 2.27(3) 2.844(3) 143(4) 8_566 _diffrn_measured_fraction_theta_max 0.961 _diffrn_reflns_theta_full 28.20 _diffrn_measured_fraction_theta_full 0.965 _refine_diff_density_max 0.818 _refine_diff_density_min -0.377 _refine_diff_density_rms 0.067 # Attachment '- Eupytzc.cif' data_struc _database_code_depnum_ccdc_archive 'CCDC 842474' #TrackingRef '- Eupytzc.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C39 H62 Eu N18 O8.50' _chemical_formula_weight 1071.03 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' Eu Eu -0.1578 3.6682 '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 14.335(4) _cell_length_b 11.098(3) _cell_length_c 30.696(8) _cell_angle_alpha 90.00 _cell_angle_beta 98.820(5) _cell_angle_gamma 90.00 _cell_volume 4826(2) _cell_formula_units_Z 4 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 954 _cell_measurement_theta_min 2.36 _cell_measurement_theta_max 23.21 _exptl_crystal_description block _exptl_crystal_colour colourless _exptl_crystal_size_max 0.20 _exptl_crystal_size_mid 0.10 _exptl_crystal_size_min 0.10 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.474 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 2212 _exptl_absorpt_coefficient_mu 1.369 _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 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 ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 17524 _diffrn_reflns_av_R_equivalents 0.0332 _diffrn_reflns_av_sigmaI/netI 0.0468 _diffrn_reflns_limit_h_min -15 _diffrn_reflns_limit_h_max 15 _diffrn_reflns_limit_k_min -12 _diffrn_reflns_limit_k_max 12 _diffrn_reflns_limit_l_min -21 _diffrn_reflns_limit_l_max 34 _diffrn_reflns_theta_min 1.81 _diffrn_reflns_theta_max 23.28 _reflns_number_total 6927 _reflns_number_gt 5651 _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^)+(0.0108P)^2^+15.2895P] 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 6927 _refine_ls_number_parameters 693 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0639 _refine_ls_R_factor_gt 0.0483 _refine_ls_wR_factor_ref 0.0824 _refine_ls_wR_factor_gt 0.0789 _refine_ls_goodness_of_fit_ref 1.146 _refine_ls_restrained_S_all 1.146 _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 Eu1 Eu 0.263939(19) 0.48766(2) 0.122007(9) 0.02580(9) Uani 1 1 d . . . O1 O 0.4173(2) 0.3961(3) 0.13206(13) 0.0347(10) Uani 1 1 d . . . O2 O 0.5174(3) 0.2413(3) 0.14460(14) 0.0403(10) Uani 1 1 d . . . O11 O 0.2757(3) 0.4721(3) 0.20031(12) 0.0366(10) Uani 1 1 d . . . O12 O 0.3317(3) 0.5230(4) 0.26932(14) 0.0557(12) Uani 1 1 d . . . O21 O 0.2473(3) 0.3722(3) 0.05490(12) 0.0330(9) Uani 1 1 d . . . O22 O 0.1894(3) 0.3366(4) -0.01551(13) 0.0400(10) Uani 1 1 d . . . N1 N 0.2718(3) 0.2629(4) 0.14337(14) 0.0264(11) Uani 1 1 d . . . N2 N 0.1075(3) 0.3875(4) 0.13041(14) 0.0279(11) Uani 1 1 d . . . N3 N 0.0155(3) 0.4216(4) 0.12585(15) 0.0336(12) Uani 1 1 d . . . N4 N -0.0360(3) 0.3278(5) 0.13245(17) 0.0411(13) Uani 1 1 d . . . N5 N 0.0198(3) 0.2291(4) 0.14161(17) 0.0393(13) Uani 1 1 d . . . N11 N 0.3791(3) 0.6348(4) 0.16806(17) 0.0313(12) Uani 1 1 d . . . N12 N 0.3506(3) 0.6380(4) 0.07878(17) 0.0389(13) Uani 1 1 d . . . N13 N 0.3496(4) 0.6629(5) 0.03619(19) 0.0557(16) Uani 1 1 d . . . N14 N 0.4081(5) 0.7536(6) 0.0330(2) 0.0702(19) Uani 1 1 d . . . N15 N 0.4492(4) 0.7886(5) 0.0735(2) 0.0624(17) Uani 1 1 d . . . N21 N 0.1469(3) 0.5701(4) 0.05703(15) 0.0255(11) Uani 1 1 d . . . N22 N 0.1669(3) 0.6702(4) 0.13800(16) 0.0307(11) Uani 1 1 d . . . N23 N 0.1561(4) 0.7337(4) 0.17382(17) 0.0394(13) Uani 1 1 d . . . N24 N 0.0928(4) 0.8193(5) 0.16234(18) 0.0421(13) Uani 1 1 d . . . N25 N 0.0619(3) 0.8128(4) 0.11891(17) 0.0399(13) Uani 1 1 d . . . C1 C 0.4376(4) 0.2874(5) 0.14162(19) 0.0309(14) Uani 1 1 d . . . C2 C 0.3563(4) 0.2090(5) 0.15076(18) 0.0292(14) Uani 1 1 d . . . C3 C 0.3668(4) 0.0909(5) 0.1641(2) 0.0381(16) Uani 1 1 d . . . H3 H 0.421(4) 0.052(5) 0.1661(18) 0.039(17) Uiso 1 1 d . . . C4 C 0.2868(5) 0.0276(6) 0.1696(2) 0.0473(19) Uani 1 1 d . . . H4 H 0.288(4) -0.035(5) 0.1799(18) 0.022(17) Uiso 1 1 d . . . C5 C 0.1995(5) 0.0806(5) 0.1626(2) 0.0376(16) Uani 1 1 d . . . H5 H 0.145(4) 0.041(5) 0.1643(17) 0.038(17) Uiso 1 1 d . . . C6 C 0.1945(4) 0.2008(5) 0.14915(17) 0.0270(13) Uani 1 1 d . . . C7 C 0.1071(4) 0.2702(5) 0.13996(18) 0.0280(13) Uani 1 1 d . . . C11 C 0.3278(4) 0.5338(5) 0.2285(2) 0.0358(15) Uani 1 1 d . . . C12 C 0.3890(4) 0.6273(5) 0.2117(2) 0.0329(14) Uani 1 1 d . . . C13 C 0.4497(5) 0.7015(7) 0.2387(3) 0.0488(19) Uani 1 1 d . . . H13 H 0.453(4) 0.693(5) 0.2668(18) 0.021(17) Uiso 1 1 d . . . C14 C 0.5024(5) 0.7852(7) 0.2197(3) 0.057(2) Uani 1 1 d . . . H14 H 0.553(5) 0.824(7) 0.232(2) 0.08(3) Uiso 1 1 d . . . C15 C 0.4935(5) 0.7925(6) 0.1746(3) 0.052(2) Uani 1 1 d . . . H15 H 0.523(4) 0.841(5) 0.1618(18) 0.024(17) Uiso 1 1 d . . . C16 C 0.4303(4) 0.7171(5) 0.1498(2) 0.0397(17) Uani 1 1 d . . . C17 C 0.4112(4) 0.7167(5) 0.1010(2) 0.0387(16) Uani 1 1 d . . . C21 C 0.1978(4) 0.3989(5) 0.0186(2) 0.0306(14) Uani 1 1 d . . . C22 C 0.1447(3) 0.5182(5) 0.01767(17) 0.0276(13) Uani 1 1 d . . . C23 C 0.0959(4) 0.5679(6) -0.0207(2) 0.0372(15) Uani 1 1 d . . . H23 H 0.094(4) 0.526(5) -0.0464(18) 0.040(17) Uiso 1 1 d . . . C24 C 0.0495(4) 0.6753(6) -0.0172(2) 0.0419(17) Uani 1 1 d . . . H24 H 0.016(4) 0.710(5) -0.044(2) 0.052(19) Uiso 1 1 d . . . C25 C 0.0498(4) 0.7281(6) 0.0229(2) 0.0379(16) Uani 1 1 d . . . H25 H 0.013(4) 0.794(6) 0.026(2) 0.06(2) Uiso 1 1 d . . . C26 C 0.0998(4) 0.6743(5) 0.06003(19) 0.0303(14) Uani 1 1 d . . . C27 C 0.1095(4) 0.7202(5) 0.10504(19) 0.0295(14) Uani 1 1 d . . . N31 N 0.6304(3) 0.4131(5) 0.11213(18) 0.0366(13) Uani 1 1 d . . . H31N H 0.601(4) 0.357(6) 0.123(2) 0.05(2) Uiso 1 1 d . . . C31 C 0.7260(4) 0.3636(6) 0.1095(2) 0.0539(19) Uani 1 1 d . . . H31A H 0.7589 0.3510 0.1392 0.065 Uiso 1 1 calc R . . H31B H 0.7614 0.4230 0.0956 0.065 Uiso 1 1 calc R . . C32 C 0.7255(5) 0.2481(6) 0.0846(3) 0.063(2) Uani 1 1 d . . . H32A H 0.6870 0.1902 0.0969 0.095 Uiso 1 1 calc R . . H32B H 0.7888 0.2179 0.0868 0.095 Uiso 1 1 calc R . . H32C H 0.7002 0.2618 0.0542 0.095 Uiso 1 1 calc R . . C33 C 0.5743(4) 0.4432(6) 0.0678(2) 0.0497(18) Uani 1 1 d . . . H33A H 0.5720 0.3727 0.0490 0.060 Uiso 1 1 calc R . . H33B H 0.5101 0.4626 0.0716 0.060 Uiso 1 1 calc R . . C34 C 0.6146(6) 0.5466(7) 0.0454(3) 0.081(3) Uani 1 1 d . . . H34A H 0.6099 0.6190 0.0620 0.122 Uiso 1 1 calc R . . H34B H 0.5800 0.5563 0.0163 0.122 Uiso 1 1 calc R . . H34C H 0.6797 0.5308 0.0436 0.122 Uiso 1 1 calc R . . C35 C 0.6327(5) 0.5163(6) 0.1433(2) 0.0574(19) Uani 1 1 d . . . H35A H 0.5721 0.5570 0.1383 0.069 Uiso 1 1 calc R . . H35B H 0.6803 0.5734 0.1372 0.069 Uiso 1 1 calc R . . C36 C 0.6542(5) 0.4780(7) 0.1912(2) 0.073(2) Uani 1 1 d . . . H36A H 0.6076 0.4210 0.1974 0.109 Uiso 1 1 calc R . . H36B H 0.6530 0.5473 0.2098 0.109 Uiso 1 1 calc R . . H36C H 0.7156 0.4415 0.1967 0.109 Uiso 1 1 calc R . . N41 N 0.1425(4) 0.4669(5) 0.27801(19) 0.0480(16) Uani 1 1 d . . . H41N H 0.194(4) 0.475(5) 0.2746(17) 0.021(17) Uiso 1 1 d . . . C41 C 0.1408(6) 0.3522(7) 0.3030(3) 0.075(3) Uani 1 1 d . . . H41A H 0.0758 0.3290 0.3036 0.090 Uiso 1 1 calc R . . H41B H 0.1709 0.3647 0.3332 0.090 Uiso 1 1 calc R . . C42 C 0.1904(7) 0.2522(7) 0.2829(4) 0.107(4) Uani 1 1 d . . . H42A H 0.1594 0.2377 0.2534 0.161 Uiso 1 1 calc R . . H42B H 0.1887 0.1803 0.3001 0.161 Uiso 1 1 calc R . . H42C H 0.2549 0.2748 0.2823 0.161 Uiso 1 1 calc R . . C43 C 0.1345(6) 0.5734(7) 0.3084(3) 0.075(2) Uani 1 1 d . . . H43A H 0.0740 0.5699 0.3188 0.090 Uiso 1 1 calc R . . H43B H 0.1836 0.5676 0.3338 0.090 Uiso 1 1 calc R . . C44 C 0.1431(7) 0.6928(7) 0.2857(3) 0.101(3) Uani 1 1 d . . . H44A H 0.2053 0.7002 0.2780 0.151 Uiso 1 1 calc R . . H44B H 0.1325 0.7572 0.3053 0.151 Uiso 1 1 calc R . . H44C H 0.0971 0.6970 0.2595 0.151 Uiso 1 1 calc R . . C45 C 0.0766(4) 0.4734(7) 0.2365(2) 0.0549(18) Uani 1 1 d . . . H45A H 0.0830 0.4010 0.2196 0.066 Uiso 1 1 calc R . . H45B H 0.0935 0.5415 0.2196 0.066 Uiso 1 1 calc R . . C46 C -0.0255(5) 0.4863(8) 0.2430(2) 0.076(2) Uani 1 1 d . . . H46A H -0.0426 0.4200 0.2603 0.114 Uiso 1 1 calc R . . H46B H -0.0652 0.4867 0.2148 0.114 Uiso 1 1 calc R . . H46C H -0.0334 0.5606 0.2581 0.114 Uiso 1 1 calc R . . N51 N 0.2902(4) 0.1217(5) 0.00459(18) 0.0427(14) Uani 1 1 d . . . H51N H 0.255(4) 0.194(5) -0.0031(17) 0.035(16) Uiso 1 1 d . . . C51 C 0.2492(6) 0.0647(7) 0.0429(3) 0.046(3) Uani 0.819(11) 1 d P A 1 H51A H 0.2743 -0.0162 0.0479 0.056 Uiso 0.819(11) 1 calc PR A 1 H51B H 0.2692 0.1112 0.0694 0.056 Uiso 0.819(11) 1 calc PR A 1 C52 C 0.1446(10) 0.0590(13) 0.0346(5) 0.055(3) Uani 0.819(11) 1 d P A 1 H52A H 0.1193 0.1391 0.0341 0.082 Uiso 0.819(11) 1 calc PR A 1 H52B H 0.1227 0.0136 0.0577 0.082 Uiso 0.819(11) 1 calc PR A 1 H52C H 0.1242 0.0205 0.0068 0.082 Uiso 0.819(11) 1 calc PR A 1 C53 C 0.2862(7) 0.0457(8) -0.0334(3) 0.050(3) Uani 0.819(11) 1 d P A 1 H53A H 0.2234 0.0113 -0.0399 0.060 Uiso 0.819(11) 1 calc PR A 1 H53B H 0.3304 -0.0203 -0.0263 0.060 Uiso 0.819(11) 1 calc PR A 1 C54 C 0.3088(8) 0.1096(10) -0.0742(4) 0.065(3) Uani 0.819(11) 1 d P A 1 H54A H 0.2656 0.1753 -0.0814 0.097 Uiso 0.819(11) 1 calc PR A 1 H54B H 0.3029 0.0539 -0.0984 0.097 Uiso 0.819(11) 1 calc PR A 1 H54C H 0.3722 0.1400 -0.0686 0.097 Uiso 0.819(11) 1 calc PR A 1 C55 C 0.3899(5) 0.1724(7) 0.0220(3) 0.042(2) Uani 0.819(11) 1 d P A 1 H55A H 0.4164 0.2058 -0.0026 0.050 Uiso 0.819(11) 1 calc PR A 1 H55B H 0.3834 0.2379 0.0423 0.050 Uiso 0.819(11) 1 calc PR A 1 C56 C 0.4574(6) 0.0825(8) 0.0448(3) 0.059(3) Uani 0.819(11) 1 d P A 1 H56A H 0.4365 0.0574 0.0717 0.088 Uiso 0.819(11) 1 calc PR A 1 H56B H 0.5189 0.1182 0.0515 0.088 Uiso 0.819(11) 1 calc PR A 1 H56C H 0.4602 0.0139 0.0261 0.088 Uiso 0.819(11) 1 calc PR A 1 C61 C 0.205(3) 0.028(4) -0.0045(16) 0.080(16) Uiso 0.181(11) 1 d P A 2 H61A H 0.1611 0.0486 -0.0307 0.096 Uiso 0.181(11) 1 calc PR A 2 H61B H 0.2273 -0.0540 -0.0069 0.096 Uiso 0.181(11) 1 calc PR A 2 C62 C 0.168(9) 0.046(13) 0.032(5) 0.19(8) Uiso 0.181(11) 1 d P A 2 H62A H 0.1057 0.0779 0.0251 0.291 Uiso 0.181(11) 1 calc PR A 2 H62B H 0.2070 0.1014 0.0511 0.291 Uiso 0.181(11) 1 calc PR A 2 H62C H 0.1657 -0.0297 0.0476 0.291 Uiso 0.181(11) 1 calc PR A 2 C63 C 0.331(4) 0.089(5) -0.0430(19) 0.070(16) Uiso 0.181(11) 1 d P A 2 H63A H 0.3944 0.1219 -0.0420 0.084 Uiso 0.181(11) 1 calc PR A 2 H63B H 0.3345 0.0027 -0.0467 0.084 Uiso 0.181(11) 1 calc PR A 2 C64 C 0.260(3) 0.149(5) -0.0846(16) 0.066(16) Uiso 0.181(11) 1 d P A 2 H64A H 0.2012 0.1059 -0.0888 0.099 Uiso 0.181(11) 1 calc PR A 2 H64B H 0.2885 0.1432 -0.1109 0.099 Uiso 0.181(11) 1 calc PR A 2 H64C H 0.2489 0.2319 -0.0785 0.099 Uiso 0.181(11) 1 calc PR A 2 C65 C 0.356(4) 0.085(5) 0.0351(17) 0.083(17) Uiso 0.181(11) 1 d P A 2 H65A H 0.3795 0.0078 0.0271 0.099 Uiso 0.181(11) 1 calc PR A 2 H65B H 0.3306 0.0755 0.0625 0.099 Uiso 0.181(11) 1 calc PR A 2 C66 C 0.436(3) 0.176(4) 0.0415(15) 0.048(12) Uiso 0.181(11) 1 d P A 2 H66A H 0.4746 0.1649 0.0191 0.072 Uiso 0.181(11) 1 calc PR A 2 H66B H 0.4727 0.1649 0.0700 0.072 Uiso 0.181(11) 1 calc PR A 2 H66C H 0.4098 0.2561 0.0394 0.072 Uiso 0.181(11) 1 calc PR A 2 O3 O 0.8655(5) 0.6231(6) 0.1157(3) 0.0789(19) Uani 1 1 d . . . H1O3 H 0.899(4) 0.615(6) 0.142(2) 0.04(2) Uiso 1 1 d . . . H2O3 H 0.871(10) 0.650(14) 0.094(5) 0.23(9) Uiso 1 1 d . . . O4 O 0.3858(9) 0.5289(13) 0.3554(5) 0.129(5) Uani 0.50 1 d P . . O5 O 0.9363(4) 0.0107(6) 0.0874(2) 0.0759(16) Uani 1 1 d . . . H1O5 H 0.985(6) 0.020(9) 0.077(3) 0.11(4) Uiso 1 1 d . . . H2O5 H 0.973(10) 0.075(13) 0.109(5) 0.24(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 Eu1 0.02497(15) 0.02093(15) 0.03267(16) 0.00237(15) 0.00811(11) -0.00062(14) O1 0.024(2) 0.032(2) 0.050(3) 0.009(2) 0.0103(19) -0.0015(18) O2 0.024(2) 0.041(2) 0.055(3) 0.013(2) 0.006(2) 0.0057(19) O11 0.036(2) 0.037(2) 0.036(2) -0.001(2) 0.0049(19) -0.0077(19) O12 0.059(3) 0.066(3) 0.041(3) -0.005(3) 0.005(2) -0.009(3) O21 0.035(2) 0.035(2) 0.029(2) -0.0015(19) 0.005(2) 0.0110(18) O22 0.041(3) 0.042(2) 0.036(3) -0.010(2) 0.004(2) 0.009(2) N1 0.026(3) 0.031(3) 0.022(2) -0.001(2) 0.006(2) -0.001(2) N2 0.025(3) 0.036(3) 0.023(3) 0.004(2) 0.005(2) 0.002(2) N3 0.028(3) 0.042(3) 0.031(3) 0.001(2) 0.004(2) 0.002(2) N4 0.026(3) 0.049(3) 0.048(3) -0.001(3) 0.007(3) -0.001(3) N5 0.028(3) 0.040(3) 0.053(4) 0.004(3) 0.016(3) -0.004(2) N11 0.024(3) 0.023(3) 0.048(4) 0.002(2) 0.011(2) -0.001(2) N12 0.036(3) 0.042(3) 0.040(3) 0.011(3) 0.013(3) 0.003(3) N13 0.051(4) 0.064(4) 0.055(4) 0.017(3) 0.019(3) -0.004(3) N14 0.068(4) 0.074(5) 0.073(5) 0.031(4) 0.025(4) -0.014(4) N15 0.059(4) 0.048(4) 0.086(5) 0.015(4) 0.029(4) -0.016(3) N21 0.020(2) 0.026(3) 0.031(3) -0.001(2) 0.009(2) -0.001(2) N22 0.032(3) 0.030(3) 0.031(3) -0.002(2) 0.006(2) 0.000(2) N23 0.047(3) 0.034(3) 0.039(3) -0.006(3) 0.014(3) -0.006(3) N24 0.049(3) 0.035(3) 0.044(4) -0.010(3) 0.015(3) -0.004(3) N25 0.043(3) 0.035(3) 0.042(4) -0.009(3) 0.010(3) 0.007(3) C1 0.026(4) 0.037(4) 0.031(4) 0.002(3) 0.010(3) 0.000(3) C2 0.031(3) 0.028(3) 0.030(3) 0.002(3) 0.009(3) 0.003(3) C3 0.028(4) 0.027(4) 0.060(5) 0.007(3) 0.009(3) 0.007(3) C4 0.055(5) 0.025(4) 0.065(5) 0.012(4) 0.017(4) 0.002(3) C5 0.033(4) 0.029(4) 0.053(4) 0.001(3) 0.014(3) -0.007(3) C6 0.025(3) 0.033(3) 0.024(3) 0.000(3) 0.005(3) -0.003(3) C7 0.024(3) 0.034(3) 0.027(3) -0.002(3) 0.008(3) -0.005(3) C11 0.030(3) 0.037(4) 0.041(4) -0.003(3) 0.008(3) 0.009(3) C12 0.024(3) 0.035(3) 0.040(4) -0.008(3) 0.004(3) 0.001(3) C13 0.040(4) 0.054(5) 0.052(5) -0.017(4) 0.003(4) 0.002(4) C14 0.029(4) 0.051(5) 0.089(7) -0.022(5) 0.000(4) -0.014(4) C15 0.039(4) 0.030(4) 0.090(7) -0.003(4) 0.017(5) -0.007(3) C16 0.038(4) 0.025(3) 0.056(5) -0.005(3) 0.007(4) 0.007(3) C17 0.023(3) 0.026(3) 0.069(5) 0.009(3) 0.013(3) -0.002(3) C21 0.025(3) 0.032(3) 0.038(4) -0.005(3) 0.015(3) -0.004(3) C22 0.023(3) 0.030(3) 0.033(3) 0.002(3) 0.011(2) -0.002(3) C23 0.038(4) 0.042(4) 0.032(4) -0.001(3) 0.005(3) 0.002(3) C24 0.040(4) 0.047(4) 0.036(4) 0.007(4) -0.003(3) 0.009(3) C25 0.037(4) 0.038(4) 0.037(4) 0.005(3) 0.000(3) 0.017(3) C26 0.023(3) 0.030(3) 0.040(4) 0.001(3) 0.011(3) -0.004(3) C27 0.029(3) 0.028(3) 0.034(4) 0.001(3) 0.011(3) -0.003(3) N31 0.025(3) 0.040(3) 0.046(4) 0.003(3) 0.010(3) -0.003(2) C31 0.028(4) 0.053(4) 0.082(6) -0.004(4) 0.010(4) 0.001(3) C32 0.050(4) 0.053(5) 0.086(6) -0.012(4) 0.010(4) 0.012(4) C33 0.038(4) 0.059(4) 0.052(4) 0.011(4) 0.009(3) -0.001(3) C34 0.102(7) 0.071(6) 0.074(6) 0.023(5) 0.027(5) -0.006(5) C35 0.053(4) 0.047(4) 0.076(5) -0.019(4) 0.018(4) -0.001(4) C36 0.085(6) 0.072(5) 0.062(5) -0.024(5) 0.014(4) -0.020(5) N41 0.044(4) 0.052(4) 0.051(4) 0.008(3) 0.017(3) 0.007(3) C41 0.069(6) 0.072(6) 0.087(7) 0.029(5) 0.017(5) 0.012(5) C42 0.116(8) 0.052(5) 0.166(10) 0.022(6) 0.063(7) 0.005(5) C43 0.090(6) 0.089(6) 0.050(5) -0.011(5) 0.026(5) 0.016(5) C44 0.160(10) 0.054(5) 0.104(8) -0.019(5) 0.066(7) -0.004(6) C45 0.060(4) 0.072(5) 0.036(4) -0.001(4) 0.016(3) 0.005(4) C46 0.059(5) 0.101(6) 0.067(5) 0.009(5) 0.004(4) 0.004(5) N51 0.040(3) 0.042(3) 0.047(4) 0.002(3) 0.007(3) 0.009(3) C51 0.043(6) 0.043(5) 0.056(6) -0.001(4) 0.016(4) -0.002(4) C52 0.042(6) 0.064(7) 0.063(7) -0.001(5) 0.022(5) -0.006(5) C53 0.048(6) 0.046(5) 0.057(6) -0.005(5) 0.010(5) 0.003(4) C54 0.068(8) 0.071(7) 0.055(7) -0.016(6) 0.011(6) 0.000(6) C55 0.027(5) 0.042(5) 0.053(6) -0.006(4) -0.003(4) -0.007(4) C56 0.037(5) 0.053(6) 0.083(7) -0.008(5) 0.000(5) 0.007(4) O3 0.076(5) 0.079(4) 0.088(6) -0.014(4) 0.032(4) -0.012(3) O4 0.117(11) 0.128(12) 0.143(12) -0.039(10) 0.023(9) 0.006(9) O5 0.065(4) 0.073(4) 0.086(4) -0.010(4) 0.003(3) 0.014(3) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag Eu1 O11 2.390(4) . ? Eu1 O1 2.399(4) . ? Eu1 O21 2.407(4) . ? Eu1 N22 2.547(4) . ? Eu1 N2 2.551(4) . ? Eu1 N12 2.567(5) . ? Eu1 N21 2.570(4) . ? Eu1 N1 2.578(4) . ? Eu1 N11 2.584(5) . ? O1 C1 1.265(6) . ? O2 C1 1.244(6) . ? O11 C11 1.257(7) . ? O12 C11 1.251(7) . ? O21 C21 1.261(7) . ? O22 C21 1.245(6) . ? N1 C2 1.338(6) . ? N1 C6 1.339(6) . ? N2 C7 1.335(7) . ? N2 N3 1.358(6) . ? N3 N4 1.310(6) . ? N4 N5 1.360(6) . ? N5 C7 1.340(7) . ? N11 C12 1.328(7) . ? N11 C16 1.346(7) . ? N12 N13 1.334(7) . ? N12 C17 1.343(7) . ? N13 N14 1.324(7) . ? N14 N15 1.348(8) . ? N15 C17 1.337(8) . ? N21 C22 1.335(6) . ? N21 C26 1.349(7) . ? N22 C27 1.325(7) . ? N22 N23 1.335(6) . ? N23 N24 1.324(7) . ? N24 N25 1.341(7) . ? N25 C27 1.339(7) . ? C1 C2 1.515(8) . ? C2 C3 1.374(8) . ? C3 C4 1.378(9) . ? C4 C5 1.369(9) . ? C5 C6 1.395(8) . ? C6 C7 1.460(7) . ? C11 C12 1.500(8) . ? C12 C13 1.379(8) . ? C13 C14 1.381(10) . ? C14 C15 1.375(11) . ? C15 C16 1.374(9) . ? C16 C17 1.481(9) . ? C21 C22 1.526(7) . ? C22 C23 1.389(8) . ? C23 C24 1.377(8) . ? C24 C25 1.362(9) . ? C25 C26 1.386(8) . ? C26 C27 1.459(8) . ? N31 C35 1.489(8) . ? N31 C31 1.490(7) . ? N31 C33 1.508(8) . ? C31 C32 1.492(9) . ? C33 C34 1.498(9) . ? C35 C36 1.516(9) . ? N41 C45 1.466(8) . ? N41 C41 1.488(9) . ? N41 C43 1.520(9) . ? C41 C42 1.501(11) . ? C43 C44 1.511(10) . ? C45 C46 1.513(9) . ? N51 C65 1.29(5) . ? N51 C53 1.432(9) . ? N51 C51 1.529(9) . ? N51 C55 1.553(9) . ? N51 C61 1.59(4) . ? N51 C63 1.69(6) . ? C51 C52 1.484(19) . ? C53 C54 1.517(14) . ? C55 C56 1.488(12) . ? C61 C62 1.34(13) . ? C63 C64 1.65(7) . ? C65 C66 1.51(6) . ? 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 O11 Eu1 O1 85.32(13) . . ? O11 Eu1 O21 143.59(13) . . ? O1 Eu1 O21 81.55(13) . . ? O11 Eu1 N22 79.62(14) . . ? O1 Eu1 N22 145.97(14) . . ? O21 Eu1 N22 127.10(14) . . ? O11 Eu1 N2 78.12(13) . . ? O1 Eu1 N2 127.24(13) . . ? O21 Eu1 N2 83.19(13) . . ? N22 Eu1 N2 79.20(14) . . ? O11 Eu1 N12 127.00(15) . . ? O1 Eu1 N12 80.52(14) . . ? O21 Eu1 N12 84.03(15) . . ? N22 Eu1 N12 84.51(15) . . ? N2 Eu1 N12 146.90(15) . . ? O11 Eu1 N21 138.00(13) . . ? O1 Eu1 N21 136.65(13) . . ? O21 Eu1 N21 63.78(13) . . ? N22 Eu1 N21 63.61(14) . . ? N2 Eu1 N21 75.78(13) . . ? N12 Eu1 N21 71.18(14) . . ? O11 Eu1 N1 71.37(13) . . ? O1 Eu1 N1 63.52(13) . . ? O21 Eu1 N1 72.37(13) . . ? N22 Eu1 N1 136.43(14) . . ? N2 Eu1 N1 63.72(14) . . ? N12 Eu1 N1 139.01(14) . . ? N21 Eu1 N1 122.68(13) . . ? O11 Eu1 N11 63.58(14) . . ? O1 Eu1 N11 72.62(13) . . ? O21 Eu1 N11 140.90(14) . . ? N22 Eu1 N11 73.35(14) . . ? N2 Eu1 N11 135.88(14) . . ? N12 Eu1 N11 63.44(16) . . ? N21 Eu1 N11 119.06(14) . . ? N1 Eu1 N11 118.26(14) . . ? C1 O1 Eu1 127.4(3) . . ? C11 O11 Eu1 126.6(4) . . ? C21 O21 Eu1 126.8(3) . . ? C2 N1 C6 119.6(5) . . ? C2 N1 Eu1 118.6(3) . . ? C6 N1 Eu1 121.8(3) . . ? C7 N2 N3 104.9(4) . . ? C7 N2 Eu1 118.7(3) . . ? N3 N2 Eu1 136.3(3) . . ? N4 N3 N2 108.9(4) . . ? N3 N4 N5 110.2(4) . . ? C7 N5 N4 104.0(5) . . ? C12 N11 C16 118.8(5) . . ? C12 N11 Eu1 118.2(4) . . ? C16 N11 Eu1 123.0(4) . . ? N13 N12 C17 105.7(5) . . ? N13 N12 Eu1 135.1(4) . . ? C17 N12 Eu1 119.2(4) . . ? N14 N13 N12 108.6(6) . . ? N13 N14 N15 110.1(6) . . ? C17 N15 N14 104.3(5) . . ? C22 N21 C26 119.3(5) . . ? C22 N21 Eu1 118.1(3) . . ? C26 N21 Eu1 121.8(4) . . ? C27 N22 N23 105.7(5) . . ? C27 N22 Eu1 118.7(4) . . ? N23 N22 Eu1 135.6(4) . . ? N24 N23 N22 108.8(5) . . ? N23 N24 N25 109.5(5) . . ? C27 N25 N24 104.5(5) . . ? O2 C1 O1 125.8(5) . . ? O2 C1 C2 118.4(5) . . ? O1 C1 C2 115.8(5) . . ? N1 C2 C3 122.1(5) . . ? N1 C2 C1 114.5(5) . . ? C3 C2 C1 123.4(5) . . ? C2 C3 C4 117.9(6) . . ? C5 C4 C3 121.3(6) . . ? C4 C5 C6 117.5(6) . . ? N1 C6 C5 121.7(5) . . ? N1 C6 C7 113.9(5) . . ? C5 C6 C7 124.4(5) . . ? N2 C7 N5 112.1(5) . . ? N2 C7 C6 121.6(5) . . ? N5 C7 C6 126.3(5) . . ? O12 C11 O11 124.6(6) . . ? O12 C11 C12 118.1(6) . . ? O11 C11 C12 117.2(5) . . ? N11 C12 C13 122.0(6) . . ? N11 C12 C11 114.4(5) . . ? C13 C12 C11 123.7(6) . . ? C12 C13 C14 118.9(7) . . ? C15 C14 C13 119.6(7) . . ? C16 C15 C14 118.2(7) . . ? N11 C16 C15 122.6(7) . . ? N11 C16 C17 113.0(5) . . ? C15 C16 C17 124.4(7) . . ? N15 C17 N12 111.3(6) . . ? N15 C17 C16 127.4(6) . . ? N12 C17 C16 121.4(5) . . ? O22 C21 O21 125.6(5) . . ? O22 C21 C22 118.8(5) . . ? O21 C21 C22 115.6(5) . . ? N21 C22 C23 122.4(5) . . ? N21 C22 C21 114.5(5) . . ? C23 C22 C21 123.1(5) . . ? C24 C23 C22 117.6(6) . . ? C25 C24 C23 120.6(6) . . ? C24 C25 C26 119.2(6) . . ? N21 C26 C25 120.9(6) . . ? N21 C26 C27 112.8(5) . . ? C25 C26 C27 126.2(5) . . ? N22 C27 N25 111.5(5) . . ? N22 C27 C26 122.3(5) . . ? N25 C27 C26 126.1(5) . . ? C35 N31 C31 112.8(5) . . ? C35 N31 C33 111.4(5) . . ? C31 N31 C33 113.6(5) . . ? N31 C31 C32 114.3(5) . . ? C34 C33 N31 113.2(6) . . ? N31 C35 C36 112.8(6) . . ? C45 N41 C41 115.5(6) . . ? C45 N41 C43 113.2(6) . . ? C41 N41 C43 109.9(6) . . ? N41 C41 C42 112.0(7) . . ? C44 C43 N41 112.4(6) . . ? N41 C45 C46 113.5(6) . . ? C65 N51 C53 110(2) . . ? C65 N51 C51 69(2) . . ? C53 N51 C51 114.2(6) . . ? C65 N51 C55 48(2) . . ? C53 N51 C55 114.4(6) . . ? C51 N51 C55 109.1(6) . . ? C65 N51 C61 112(3) . . ? C53 N51 C61 62.5(17) . . ? C51 N51 C61 59.5(18) . . ? C55 N51 C61 159.3(18) . . ? C65 N51 C63 104(3) . . ? C53 N51 C63 31.8(19) . . ? C51 N51 C63 143(2) . . ? C55 N51 C63 87(2) . . ? C61 N51 C63 94(3) . . ? C52 C51 N51 112.5(8) . . ? N51 C53 C54 114.2(7) . . ? C56 C55 N51 114.6(7) . . ? C62 C61 N51 98(7) . . ? C64 C63 N51 109(3) . . ? N51 C65 C66 110(4) . . ? 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 N31 H31N O2 0.84(6) 1.95(6) 2.784(6) 172(6) . N41 H41N O12 0.77(5) 2.07(5) 2.835(7) 172(6) . N51 H51N O22 0.96(5) 1.85(6) 2.808(7) 178(5) . O3 H2O3 O22 0.73(14) 2.45(14) 3.089(10) 147(15) 3_665 O5 H2O5 N5 1.07(15) 2.03(15) 3.077(8) 165(11) 1_655 _diffrn_measured_fraction_theta_max 0.995 _diffrn_reflns_theta_full 23.28 _diffrn_measured_fraction_theta_full 0.995 _refine_diff_density_max 0.867 _refine_diff_density_min -1.623 _refine_diff_density_rms 0.090