# Electronic Supplementary Material (ESI) for Dalton Transactions # This journal is © The Royal Society of Chemistry 2012 data_global _journal_name_full 'Dalton Trans.' _journal_coden_cambridge 0222 _journal_year ? _journal_volume ? _journal_page_first ? _publ_contact_author_email wangjianweilzu@163.com _publ_contact_author_name 'Jianwei Wang' loop_ _publ_author_name 'Jianwei wang' 'Jiang Wu' 'Haiping Wang' 'Yiran Li' 'Hao Tian' ; Ting Zhang ; 'Jun Xu' 'Yu Tang' # Attachment '- 891974_revision.cif' data_t _database_code_depnum_ccdc_archive 'CCDC 891974' #TrackingRef '- 891974_revision.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety '2(C24 H32 Eu N5 O14), C H3 N O2' _chemical_formula_sum 'C49 H67 Eu2 N11 O30' _chemical_formula_weight 1594.06 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' Eu Eu -0.1578 3.6682 '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 'C 2/c' _symmetry_space_group_name_Hall '-C 2yc' 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 27.329(4) _cell_length_b 14.0485(18) _cell_length_c 20.865(3) _cell_angle_alpha 90.000(8) _cell_angle_beta 126.997(6) _cell_angle_gamma 90.000(8) _cell_volume 6397.9(15) _cell_formula_units_Z 4 _cell_measurement_temperature 296(2) _cell_measurement_reflns_used 3145 _cell_measurement_theta_min 2.412 _cell_measurement_theta_max 20.005 _exptl_crystal_description block _exptl_crystal_colour colourless _exptl_crystal_size_max 0.28 _exptl_crystal_size_mid 0.25 _exptl_crystal_size_min 0.23 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.655 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 3216 _exptl_absorpt_coefficient_mu 2.038 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.5992 _exptl_absorpt_correction_T_max 0.6515 _exptl_absorpt_process_details 'SADABS (Bruker 2008)' _exptl_special_details ; ? ; _diffrn_ambient_temperature 296(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 'Bruker APEX-II CCD' _diffrn_measurement_method '\f and \w scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number 0 _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 23510 _diffrn_reflns_av_R_equivalents 0.0805 _diffrn_reflns_av_sigmaI/netI 0.0728 _diffrn_reflns_limit_h_min -32 _diffrn_reflns_limit_h_max 32 _diffrn_reflns_limit_k_min -15 _diffrn_reflns_limit_k_max 16 _diffrn_reflns_limit_l_min -24 _diffrn_reflns_limit_l_max 24 _diffrn_reflns_theta_min 1.72 _diffrn_reflns_theta_max 25.00 _reflns_number_total 5642 _reflns_number_gt 3450 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker APEX2' _computing_cell_refinement 'Bruker SAINT' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'SHELXS-97 (Sheldrick, 2008)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _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. Due to the serious disorder of prop-2-en-1-ol group, 26 restraints were applied to refine it. ; _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^)+(0.1277P)^2^+34.9150P] 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 5642 _refine_ls_number_parameters 421 _refine_ls_number_restraints 26 _refine_ls_R_factor_all 0.1182 _refine_ls_R_factor_gt 0.0749 _refine_ls_wR_factor_ref 0.2466 _refine_ls_wR_factor_gt 0.1938 _refine_ls_goodness_of_fit_ref 1.080 _refine_ls_restrained_S_all 1.083 _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 0.0654(4) 0.8906(6) 0.4749(5) 0.078(2) Uani 1 1 d . . . N1 N 0.0165(4) 0.7278(8) 0.3965(6) 0.070(2) Uani 1 1 d . . . C1 C -0.0065(5) 0.8118(10) 0.3552(7) 0.071(3) Uani 1 1 d . . . Eu2 Eu 0.09036(3) 0.72982(4) 0.55201(4) 0.0683(3) Uani 1 1 d . . . O2 O 0.1484(4) 0.8635(6) 0.6230(4) 0.081(2) Uani 1 1 d . . . C2 C 0.0181(5) 0.8985(9) 0.3956(7) 0.071(3) Uani 1 1 d . . . N2 N 0.1833(4) 1.0142(7) 0.6539(6) 0.079(3) Uani 1 1 d . . . O3 O 0.0739(4) 0.5759(6) 0.4862(5) 0.080(2) Uani 1 1 d . . . N3 N 0.2065(6) 0.7143(10) 0.5770(9) 0.098(4) Uani 1 1 d . . . C3 C -0.0066(6) 0.9803(11) 0.3547(8) 0.091(4) Uani 1 1 d . . . H3 H 0.0080 1.0382 0.3817 0.110 Uiso 1 1 calc R . . C4 C -0.0541(7) 0.9794(12) 0.2718(10) 0.104(5) Uani 1 1 d . . . H4 H -0.0698 1.0369 0.2447 0.124 Uiso 1 1 calc R . . N4 N -0.0287(6) 0.7507(11) 0.5209(7) 0.096(4) Uani 1 1 d . . . O4 O 0.0483(5) 0.5042(8) 0.3749(6) 0.122(4) Uani 1 1 d . . . N5 N 0.1089(5) 0.6370(10) 0.6913(7) 0.089(3) Uani 1 1 d . . . C5 C -0.0778(7) 0.8960(13) 0.2298(9) 0.104(5) Uani 1 1 d . . . H5 H -0.1092 0.8975 0.1750 0.125 Uiso 1 1 calc R . . O5 O 0.2107(8) 0.4540(15) 0.4913(9) 0.177(5) Uani 1 1 d DU . . C6 C -0.0552(6) 0.8093(11) 0.2689(8) 0.080(3) Uani 1 1 d . . . O6 O 0.1602(5) 0.7495(7) 0.5138(7) 0.098(3) Uani 1 1 d . . . N6 N 1.0000 0.772(3) 0.7500 0.203(16) Uani 1 2 d S . . O7 O 0.1967(4) 0.6766(7) 0.6227(6) 0.090(2) Uani 1 1 d . . . C7 C -0.0756(6) 0.7209(12) 0.2368(8) 0.089(4) Uani 1 1 d . . . H7 H -0.1088 0.7174 0.1828 0.107 Uiso 1 1 calc R . . C8 C -0.0521(7) 0.6391(12) 0.2758(9) 0.100(5) Uani 1 1 d . . . H8 H -0.0660 0.5810 0.2492 0.120 Uiso 1 1 calc R . . O8 O 0.2575(6) 0.7164(10) 0.5940(9) 0.136(5) Uani 1 1 d . . . O9 O 0.0026(4) 0.8214(7) 0.5291(6) 0.095(3) Uani 1 1 d . . . C9 C -0.0050(5) 0.6440(10) 0.3598(7) 0.078(3) Uani 1 1 d . . . O10 O -0.0083(4) 0.6718(7) 0.5184(6) 0.088(2) Uani 1 1 d . . . C10 C 0.0925(6) 0.9768(9) 0.5187(7) 0.080(3) Uani 1 1 d . . . H10A H 0.0623 1.0149 0.5174 0.096 Uiso 1 1 calc R . . H10B H 0.1081 1.0136 0.4951 0.096 Uiso 1 1 calc R . . O11 O -0.0739(6) 0.7594(9) 0.5174(10) 0.131(5) Uani 1 1 d . . . C11 C 0.1436(5) 0.9505(9) 0.6031(7) 0.071(3) Uani 1 1 d . . . O12 O 0.1030(5) 0.7270(7) 0.6810(6) 0.094(3) Uani 1 1 d . . . C12 C 0.1754(6) 1.1166(9) 0.6332(8) 0.083(3) Uani 1 1 d . . . H12 H 0.1451 1.1220 0.5749 0.099 Uiso 1 1 calc R . . O13 O 0.1101(4) 0.5914(7) 0.6411(6) 0.092(3) Uani 1 1 d . . . C13 C 0.1502(7) 1.1686(11) 0.6713(10) 0.111(5) Uani 1 1 d . . . H13A H 0.1174 1.1321 0.6640 0.167 Uiso 1 1 calc R . . H13B H 0.1350 1.2298 0.6465 0.167 Uiso 1 1 calc R . . H13C H 0.1821 1.1767 0.7276 0.167 Uiso 1 1 calc R . . C14 C 0.2341(7) 1.1604(11) 0.6559(10) 0.108(5) Uani 1 1 d . . . H14A H 0.2656 1.1518 0.7123 0.162 Uiso 1 1 calc R . . H14B H 0.2280 1.2271 0.6436 0.162 Uiso 1 1 calc R . . H14C H 0.2463 1.1301 0.6262 0.162 Uiso 1 1 calc R . . O14 O 0.1116(5) 0.5989(9) 0.7450(6) 0.115(3) Uani 1 1 d . . . C15 C 0.2343(6) 0.9861(9) 0.7374(7) 0.086(4) Uani 1 1 d . . . H15 H 0.2569 1.0445 0.7655 0.103 Uiso 1 1 calc R . . O15 O 0.966(2) 0.807(3) 0.694(2) 0.40(3) Uani 1 1 d . . . C16 C 0.2106(8) 0.9456(12) 0.7830(9) 0.114(5) Uani 1 1 d . . . H16A H 0.2000 0.8798 0.7692 0.170 Uiso 1 1 calc R . . H16B H 0.1750 0.9806 0.7682 0.170 Uiso 1 1 calc R . . H16C H 0.2419 0.9513 0.8397 0.170 Uiso 1 1 calc R . . C17 C 0.2791(6) 0.9200(11) 0.7397(9) 0.105(5) Uani 1 1 d . . . H17A H 0.2651 0.8555 0.7326 0.158 Uiso 1 1 calc R . . H17B H 0.3187 0.9260 0.7904 0.158 Uiso 1 1 calc R . . H17C H 0.2819 0.9365 0.6973 0.158 Uiso 1 1 calc R . . C18 C 0.0241(6) 0.5563(10) 0.4060(8) 0.086(4) Uani 1 1 d . . . H18 H -0.0063 0.5177 0.4050 0.103 Uiso 1 1 calc R . . C19 C 0.1130(7) 0.4942(9) 0.5134(9) 0.094(4) Uani 1 1 d . . . H19A H 0.1007 0.4459 0.5344 0.113 Uiso 1 1 calc R . . H19B H 0.1554 0.5114 0.5546 0.113 Uiso 1 1 calc R . . C20 C 0.1040(9) 0.4596(16) 0.4378(9) 0.133(5) Uani 1 1 d U . . H20 H 0.1019 0.3901 0.4332 0.159 Uiso 1 1 calc R . . C21 C 0.1547(10) 0.5031(17) 0.4324(11) 0.150(5) Uani 1 1 d U . . H21A H 0.1437 0.4938 0.3792 0.180 Uiso 1 1 calc R . . H21B H 0.1592 0.5708 0.4438 0.180 Uiso 1 1 calc R . . C22 C 0.2618(12) 0.505(2) 0.4996(18) 0.221(11) Uani 1 1 d DU . . H22A H 0.2693 0.5664 0.5258 0.266 Uiso 1 1 calc R . . H22B H 0.2530 0.5156 0.4476 0.266 Uiso 1 1 calc R . . C23 C 0.3158(11) 0.440(3) 0.551(2) 0.215(11) Uani 1 1 d DU . . H23 H 0.3547 0.4608 0.5699 0.258 Uiso 1 1 calc R . . C24 C 0.3092(16) 0.353(2) 0.568(2) 0.28(2) Uani 1 1 d D . . H24A H 0.2706 0.3308 0.5493 0.341 Uiso 1 1 calc R . . H24B H 0.3433 0.3137 0.5999 0.341 Uiso 1 1 calc R . . C25 C 1.0000 0.679(2) 0.7500 0.187(17) Uani 1 2 d S . . H25A H 1.0373 0.6564 0.7606 0.281 Uiso 0.50 1 calc PR . . H25B H 0.9657 0.6564 0.6986 0.281 Uiso 0.50 1 calc PR . . H25C H 0.9969 0.6564 0.7909 0.281 Uiso 0.50 1 calc PR . . 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 0.085(5) 0.063(5) 0.066(5) -0.003(4) 0.035(4) -0.011(4) N1 0.065(5) 0.074(7) 0.062(6) -0.007(5) 0.033(5) -0.001(5) C1 0.064(6) 0.079(8) 0.064(7) 0.001(7) 0.036(6) 0.007(6) Eu2 0.0722(4) 0.0578(4) 0.0668(4) -0.0023(3) 0.0375(3) -0.0024(3) O2 0.087(5) 0.075(6) 0.059(4) 0.003(4) 0.032(4) -0.002(4) C2 0.076(7) 0.072(8) 0.057(7) 0.008(6) 0.036(6) -0.005(6) N2 0.070(6) 0.070(7) 0.072(6) -0.004(5) 0.030(5) -0.005(5) O3 0.090(5) 0.059(5) 0.075(5) -0.009(4) 0.041(5) 0.002(4) N3 0.083(9) 0.103(10) 0.103(10) -0.017(8) 0.054(8) -0.006(7) C3 0.076(8) 0.090(10) 0.083(9) 0.008(8) 0.034(8) -0.012(7) C4 0.094(10) 0.095(11) 0.108(11) 0.032(10) 0.053(9) 0.001(9) N4 0.074(7) 0.145(13) 0.078(8) 0.023(7) 0.051(6) 0.019(8) O4 0.121(8) 0.115(8) 0.083(6) -0.034(6) 0.036(6) 0.030(6) N5 0.091(8) 0.097(10) 0.075(7) 0.005(7) 0.048(6) -0.002(7) C5 0.083(9) 0.122(14) 0.076(9) 0.022(9) 0.032(8) 0.000(9) O5 0.162(11) 0.226(13) 0.131(9) -0.004(9) 0.081(8) 0.018(9) C6 0.081(8) 0.080(8) 0.075(8) -0.003(8) 0.045(7) 0.005(7) O6 0.082(6) 0.122(8) 0.084(7) 0.007(6) 0.048(6) 0.002(5) N6 0.29(6) 0.18(4) 0.17(4) 0.000 0.15(4) 0.000 O7 0.093(6) 0.081(6) 0.097(6) 0.001(5) 0.057(6) 0.002(5) C7 0.078(8) 0.103(12) 0.062(8) 0.006(8) 0.030(7) 0.013(8) C8 0.097(10) 0.095(11) 0.089(10) -0.038(9) 0.045(8) -0.014(9) O8 0.083(7) 0.184(14) 0.144(11) 0.006(9) 0.071(8) 0.004(7) O9 0.091(6) 0.091(7) 0.109(7) 0.011(6) 0.065(6) 0.007(5) C9 0.068(7) 0.089(10) 0.069(8) -0.014(7) 0.036(6) 0.001(7) O10 0.081(6) 0.087(7) 0.098(6) -0.003(5) 0.054(5) 0.002(5) C10 0.088(8) 0.063(8) 0.086(8) -0.004(7) 0.050(7) -0.010(6) O11 0.117(9) 0.135(10) 0.179(13) 0.061(8) 0.109(9) 0.045(7) C11 0.079(8) 0.063(7) 0.070(7) 0.009(6) 0.044(6) 0.004(6) O12 0.117(8) 0.082(7) 0.083(6) -0.003(5) 0.059(6) -0.006(5) C12 0.086(8) 0.061(8) 0.076(8) 0.000(6) 0.036(7) -0.001(6) O13 0.108(7) 0.075(6) 0.102(7) 0.013(5) 0.068(6) 0.014(5) C13 0.105(11) 0.081(10) 0.133(13) -0.013(9) 0.064(10) 0.002(8) C14 0.108(11) 0.078(10) 0.129(12) 0.000(9) 0.067(10) -0.009(8) O14 0.134(9) 0.125(9) 0.098(7) 0.023(6) 0.077(7) 0.001(7) C15 0.087(9) 0.067(8) 0.081(9) -0.013(6) 0.038(7) -0.009(7) O15 0.62(8) 0.31(4) 0.27(4) 0.15(3) 0.28(5) 0.17(4) C16 0.136(13) 0.104(12) 0.083(9) -0.016(9) 0.056(10) -0.014(10) C17 0.081(9) 0.083(10) 0.116(11) -0.007(8) 0.040(8) 0.004(8) C18 0.083(8) 0.070(8) 0.076(8) -0.009(7) 0.032(7) -0.001(7) C19 0.101(10) 0.067(8) 0.101(10) 0.004(7) 0.053(8) 0.008(7) C20 0.154(11) 0.156(13) 0.079(7) -0.007(8) 0.066(8) 0.046(10) C21 0.165(11) 0.200(13) 0.095(8) -0.005(8) 0.083(8) 0.039(9) C22 0.22(3) 0.22(3) 0.22(3) 0.000(19) 0.13(2) 0.000(18) C23 0.22(3) 0.22(3) 0.22(3) 0.00(2) 0.13(2) 0.000(18) C24 0.28(4) 0.28(6) 0.28(5) 0.00(4) 0.17(4) 0.00(4) C25 0.17(3) 0.075(19) 0.31(5) 0.000 0.14(3) 0.000 _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 C2 1.358(13) . ? O1 C10 1.426(14) . ? O1 Eu2 2.615(8) . ? N1 C9 1.333(15) . ? N1 C1 1.371(16) . ? N1 Eu2 2.593(10) . ? C1 C2 1.402(17) . ? C1 C6 1.460(17) . ? Eu2 O2 2.326(8) . ? Eu2 O3 2.454(8) . ? Eu2 O7 2.455(9) . ? Eu2 O10 2.479(9) . ? Eu2 O6 2.486(10) . ? Eu2 O12 2.500(10) . ? Eu2 O9 2.501(9) . ? Eu2 O13 2.514(9) . ? O2 C11 1.272(14) . ? C2 C3 1.346(18) . ? N2 C11 1.310(15) . ? N2 C12 1.480(16) . ? N2 C15 1.488(15) . ? O3 C18 1.409(14) . ? O3 C19 1.432(15) . ? N3 O8 1.213(16) . ? N3 O7 1.253(16) . ? N3 O6 1.255(16) . ? C3 C4 1.41(2) . ? C3 H3 0.9300 . ? C4 C5 1.37(2) . ? C4 H4 0.9300 . ? N4 O11 1.198(16) . ? N4 O9 1.253(16) . ? N4 O10 1.257(15) . ? O4 C18 1.382(16) . ? O4 C20 1.424(19) . ? N5 O14 1.203(13) . ? N5 O13 1.246(14) . ? N5 O12 1.276(14) . ? C5 C6 1.39(2) . ? C5 H5 0.9300 . ? O5 C21 1.44(2) . ? O5 C22 1.486(10) . ? C6 C7 1.36(2) . ? N6 O15 1.08(3) 2_756 ? N6 O15 1.08(3) . ? N6 C25 1.30(5) . ? C7 C8 1.33(2) . ? C7 H7 0.9300 . ? C8 C9 1.419(18) . ? C8 H8 0.9300 . ? C9 C18 1.468(19) . ? C10 C11 1.493(16) . ? C10 H10A 0.9700 . ? C10 H10B 0.9700 . ? C12 C14 1.505(19) . ? C12 C13 1.516(19) . ? C12 H12 0.9800 . ? C13 H13A 0.9600 . ? C13 H13B 0.9600 . ? C13 H13C 0.9600 . ? C14 H14A 0.9600 . ? C14 H14B 0.9600 . ? C14 H14C 0.9600 . ? C15 C17 1.516(18) . ? C15 C16 1.55(2) . ? C15 H15 0.9800 . ? C16 H16A 0.9600 . ? C16 H16B 0.9600 . ? C16 H16C 0.9600 . ? C17 H17A 0.9600 . ? C17 H17B 0.9600 . ? C17 H17C 0.9600 . ? C18 H18 0.9800 . ? C19 C20 1.52(2) . ? C19 H19A 0.9700 . ? C19 H19B 0.9700 . ? C20 C21 1.58(3) . ? C20 H20 0.9800 . ? C21 H21A 0.9700 . ? C21 H21B 0.9700 . ? C22 C23 1.507(10) . ? C22 H22A 0.9700 . ? C22 H22B 0.9700 . ? C23 C24 1.318(10) . ? C23 H23 0.9300 . ? C24 H24A 0.9300 . ? C24 H24B 0.9300 . ? C25 H25A 0.9600 . ? C25 H25B 0.9600 . ? C25 H25C 0.9600 . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C2 O1 C10 117.2(9) . . ? C2 O1 Eu2 121.6(7) . . ? C10 O1 Eu2 119.8(7) . . ? C9 N1 C1 121.5(10) . . ? C9 N1 Eu2 118.1(8) . . ? C1 N1 Eu2 119.6(8) . . ? N1 C1 C2 119.8(10) . . ? N1 C1 C6 119.2(12) . . ? C2 C1 C6 121.0(12) . . ? O2 Eu2 O3 153.3(3) . . ? O2 Eu2 O7 75.9(3) . . ? O3 Eu2 O7 79.6(3) . . ? O2 Eu2 O10 130.9(3) . . ? O3 Eu2 O10 75.5(3) . . ? O7 Eu2 O10 139.7(3) . . ? O2 Eu2 O6 75.7(3) . . ? O3 Eu2 O6 80.6(3) . . ? O7 Eu2 O6 50.7(3) . . ? O10 Eu2 O6 149.2(3) . . ? O2 Eu2 O12 74.2(3) . . ? O3 Eu2 O12 116.6(3) . . ? O7 Eu2 O12 90.1(4) . . ? O10 Eu2 O12 73.8(3) . . ? O6 Eu2 O12 135.4(4) . . ? O2 Eu2 O9 85.1(3) . . ? O3 Eu2 O9 120.9(3) . . ? O7 Eu2 O9 157.6(3) . . ? O10 Eu2 O9 50.3(3) . . ? O6 Eu2 O9 135.6(3) . . ? O12 Eu2 O9 73.1(3) . . ? O2 Eu2 O13 113.2(3) . . ? O3 Eu2 O13 67.5(3) . . ? O7 Eu2 O13 70.8(3) . . ? O10 Eu2 O13 70.6(3) . . ? O6 Eu2 O13 117.3(3) . . ? O12 Eu2 O13 50.4(3) . . ? O9 Eu2 O13 107.1(3) . . ? O2 Eu2 N1 121.7(3) . . ? O3 Eu2 N1 63.1(3) . . ? O7 Eu2 N1 119.8(3) . . ? O10 Eu2 N1 75.4(3) . . ? O6 Eu2 N1 76.7(3) . . ? O12 Eu2 N1 147.8(4) . . ? O9 Eu2 N1 80.3(3) . . ? O13 Eu2 N1 125.1(3) . . ? O2 Eu2 O1 61.3(3) . . ? O3 Eu2 O1 121.7(3) . . ? O7 Eu2 O1 114.2(3) . . ? O10 Eu2 O1 105.9(3) . . ? O6 Eu2 O1 70.9(3) . . ? O12 Eu2 O1 119.5(3) . . ? O9 Eu2 O1 64.7(3) . . ? O13 Eu2 O1 169.6(3) . . ? N1 Eu2 O1 61.4(3) . . ? C11 O2 Eu2 132.1(7) . . ? C3 C2 O1 126.1(12) . . ? C3 C2 C1 119.0(11) . . ? O1 C2 C1 115.0(10) . . ? C11 N2 C12 121.6(10) . . ? C11 N2 C15 120.2(10) . . ? C12 N2 C15 117.9(10) . . ? C18 O3 C19 105.8(9) . . ? C18 O3 Eu2 123.8(7) . . ? C19 O3 Eu2 130.0(7) . . ? O8 N3 O7 121.4(15) . . ? O8 N3 O6 123.6(16) . . ? O7 N3 O6 115.0(12) . . ? C2 C3 C4 120.8(14) . . ? C2 C3 H3 119.6 . . ? C4 C3 H3 119.6 . . ? C5 C4 C3 121.7(14) . . ? C5 C4 H4 119.1 . . ? C3 C4 H4 119.1 . . ? O11 N4 O9 121.4(15) . . ? O11 N4 O10 123.7(15) . . ? O9 N4 O10 114.9(11) . . ? C18 O4 C20 110.5(10) . . ? O14 N5 O13 122.5(14) . . ? O14 N5 O12 121.8(13) . . ? O13 N5 O12 115.7(11) . . ? C4 C5 C6 120.3(13) . . ? C4 C5 H5 119.9 . . ? C6 C5 H5 119.9 . . ? C21 O5 C22 108(2) . . ? C7 C6 C5 127.4(13) . . ? C7 C6 C1 115.4(13) . . ? C5 C6 C1 117.2(14) . . ? N3 O6 Eu2 96.0(9) . . ? O15 N6 O15 125(7) 2_756 . ? O15 N6 C25 117(4) 2_756 . ? O15 N6 C25 117(4) . . ? N3 O7 Eu2 97.6(8) . . ? C8 C7 C6 125.7(13) . . ? C8 C7 H7 117.2 . . ? C6 C7 H7 117.2 . . ? C7 C8 C9 117.4(13) . . ? C7 C8 H8 121.3 . . ? C9 C8 H8 121.3 . . ? N4 O9 Eu2 96.6(8) . . ? N1 C9 C8 120.7(13) . . ? N1 C9 C18 119.1(11) . . ? C8 C9 C18 120.1(13) . . ? N4 O10 Eu2 97.6(8) . . ? O1 C10 C11 107.6(10) . . ? O1 C10 H10A 110.2 . . ? C11 C10 H10A 110.2 . . ? O1 C10 H10B 110.2 . . ? C11 C10 H10B 110.2 . . ? H10A C10 H10B 108.5 . . ? O2 C11 N2 121.3(11) . . ? O2 C11 C10 117.6(11) . . ? N2 C11 C10 121.1(11) . . ? N5 O12 Eu2 96.8(8) . . ? N2 C12 C14 111.4(11) . . ? N2 C12 C13 110.3(11) . . ? C14 C12 C13 112.0(12) . . ? N2 C12 H12 107.6 . . ? C14 C12 H12 107.6 . . ? C13 C12 H12 107.6 . . ? N5 O13 Eu2 97.0(8) . . ? C12 C13 H13A 109.5 . . ? C12 C13 H13B 109.5 . . ? H13A C13 H13B 109.5 . . ? C12 C13 H13C 109.5 . . ? H13A C13 H13C 109.5 . . ? H13B C13 H13C 109.5 . . ? C12 C14 H14A 109.5 . . ? C12 C14 H14B 109.5 . . ? H14A C14 H14B 109.5 . . ? C12 C14 H14C 109.5 . . ? H14A C14 H14C 109.5 . . ? H14B C14 H14C 109.5 . . ? N2 C15 C17 111.7(11) . . ? N2 C15 C16 111.9(11) . . ? C17 C15 C16 112.7(13) . . ? N2 C15 H15 106.7 . . ? C17 C15 H15 106.7 . . ? C16 C15 H15 106.7 . . ? C15 C16 H16A 109.5 . . ? C15 C16 H16B 109.5 . . ? H16A C16 H16B 109.5 . . ? C15 C16 H16C 109.5 . . ? H16A C16 H16C 109.5 . . ? H16B C16 H16C 109.5 . . ? C15 C17 H17A 109.5 . . ? C15 C17 H17B 109.5 . . ? H17A C17 H17B 109.5 . . ? C15 C17 H17C 109.5 . . ? H17A C17 H17C 109.5 . . ? H17B C17 H17C 109.5 . . ? O4 C18 O3 105.5(11) . . ? O4 C18 C9 111.0(12) . . ? O3 C18 C9 111.8(11) . . ? O4 C18 H18 109.5 . . ? O3 C18 H18 109.5 . . ? C9 C18 H18 109.5 . . ? O3 C19 C20 103.2(12) . . ? O3 C19 H19A 111.1 . . ? C20 C19 H19A 111.1 . . ? O3 C19 H19B 111.1 . . ? C20 C19 H19B 111.1 . . ? H19A C19 H19B 109.1 . . ? O4 C20 C19 103.3(12) . . ? O4 C20 C21 105.3(16) . . ? C19 C20 C21 110.4(16) . . ? O4 C20 H20 112.4 . . ? C19 C20 H20 112.4 . . ? C21 C20 H20 112.4 . . ? O5 C21 C20 106.5(18) . . ? O5 C21 H21A 110.4 . . ? C20 C21 H21A 110.4 . . ? O5 C21 H21B 110.4 . . ? C20 C21 H21B 110.4 . . ? H21A C21 H21B 108.6 . . ? O5 C22 C23 103.7(16) . . ? O5 C22 H22A 111.0 . . ? C23 C22 H22A 111.0 . . ? O5 C22 H22B 111.0 . . ? C23 C22 H22B 111.0 . . ? H22A C22 H22B 109.0 . . ? C24 C23 C22 121.7(13) . . ? C24 C23 H23 119.2 . . ? C22 C23 H23 119.2 . . ? C23 C24 H24A 120.0 . . ? C23 C24 H24B 120.0 . . ? H24A C24 H24B 120.0 . . ? N6 C25 H25A 109.5 . . ? N6 C25 H25B 109.5 . . ? H25A C25 H25B 109.5 . . ? N6 C25 H25C 109.5 . . ? H25A C25 H25C 109.5 . . ? H25B C25 H25C 109.5 . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag C9 N1 C1 C2 -178.9(11) . . . . ? Eu2 N1 C1 C2 11.4(14) . . . . ? C9 N1 C1 C6 -0.7(17) . . . . ? Eu2 N1 C1 C6 -170.4(8) . . . . ? C9 N1 Eu2 O2 165.9(8) . . . . ? C1 N1 Eu2 O2 -24.1(9) . . . . ? C9 N1 Eu2 O3 16.1(8) . . . . ? C1 N1 Eu2 O3 -173.8(9) . . . . ? C9 N1 Eu2 O7 74.6(9) . . . . ? C1 N1 Eu2 O7 -115.4(8) . . . . ? C9 N1 Eu2 O10 -64.8(9) . . . . ? C1 N1 Eu2 O10 105.3(8) . . . . ? C9 N1 Eu2 O6 102.2(9) . . . . ? C1 N1 Eu2 O6 -87.7(8) . . . . ? C9 N1 Eu2 O12 -81.8(10) . . . . ? C1 N1 Eu2 O12 88.3(10) . . . . ? C9 N1 Eu2 O9 -116.1(9) . . . . ? C1 N1 Eu2 O9 54.0(8) . . . . ? C9 N1 Eu2 O13 -12.0(10) . . . . ? C1 N1 Eu2 O13 158.1(7) . . . . ? C9 N1 Eu2 O1 177.5(10) . . . . ? C1 N1 Eu2 O1 -12.4(7) . . . . ? C2 O1 Eu2 O2 -177.4(9) . . . . ? C10 O1 Eu2 O2 -11.1(8) . . . . ? C2 O1 Eu2 O3 33.4(9) . . . . ? C10 O1 Eu2 O3 -160.3(8) . . . . ? C2 O1 Eu2 O7 126.0(8) . . . . ? C10 O1 Eu2 O7 -67.7(9) . . . . ? C2 O1 Eu2 O10 -49.1(9) . . . . ? C10 O1 Eu2 O10 117.2(8) . . . . ? C2 O1 Eu2 O6 98.8(9) . . . . ? C10 O1 Eu2 O6 -94.9(9) . . . . ? C2 O1 Eu2 O12 -129.2(8) . . . . ? C10 O1 Eu2 O12 37.1(9) . . . . ? C2 O1 Eu2 O9 -78.7(9) . . . . ? C10 O1 Eu2 O9 87.6(9) . . . . ? C2 O1 Eu2 O13 -117.5(16) . . . . ? C10 O1 Eu2 O13 48.8(19) . . . . ? C2 O1 Eu2 N1 13.9(8) . . . . ? C10 O1 Eu2 N1 -179.8(9) . . . . ? O3 Eu2 O2 C11 110.5(11) . . . . ? O7 Eu2 O2 C11 134.6(11) . . . . ? O10 Eu2 O2 C11 -80.1(11) . . . . ? O6 Eu2 O2 C11 82.2(11) . . . . ? O12 Eu2 O2 C11 -131.2(11) . . . . ? O9 Eu2 O2 C11 -57.4(11) . . . . ? O13 Eu2 O2 C11 -163.9(10) . . . . ? N1 Eu2 O2 C11 18.0(12) . . . . ? O1 Eu2 O2 C11 6.3(10) . . . . ? C10 O1 C2 C3 -1.7(18) . . . . ? Eu2 O1 C2 C3 165.0(11) . . . . ? C10 O1 C2 C1 179.4(10) . . . . ? Eu2 O1 C2 C1 -14.0(13) . . . . ? N1 C1 C2 C3 -177.5(12) . . . . ? C6 C1 C2 C3 4.3(18) . . . . ? N1 C1 C2 O1 1.5(16) . . . . ? C6 C1 C2 O1 -176.7(10) . . . . ? O2 Eu2 O3 C18 -125.5(10) . . . . ? O7 Eu2 O3 C18 -149.3(10) . . . . ? O10 Eu2 O3 C18 62.7(10) . . . . ? O6 Eu2 O3 C18 -97.8(10) . . . . ? O12 Eu2 O3 C18 125.8(10) . . . . ? O9 Eu2 O3 C18 40.4(11) . . . . ? O13 Eu2 O3 C18 137.4(10) . . . . ? N1 Eu2 O3 C18 -18.0(9) . . . . ? O1 Eu2 O3 C18 -37.2(11) . . . . ? O2 Eu2 O3 C19 45.9(13) . . . . ? O7 Eu2 O3 C19 22.1(10) . . . . ? O10 Eu2 O3 C19 -125.9(11) . . . . ? O6 Eu2 O3 C19 73.6(11) . . . . ? O12 Eu2 O3 C19 -62.8(11) . . . . ? O9 Eu2 O3 C19 -148.3(10) . . . . ? O13 Eu2 O3 C19 -51.2(10) . . . . ? N1 Eu2 O3 C19 153.4(11) . . . . ? O1 Eu2 O3 C19 134.2(10) . . . . ? O1 C2 C3 C4 177.6(12) . . . . ? C1 C2 C3 C4 -3(2) . . . . ? C2 C3 C4 C5 1(2) . . . . ? C3 C4 C5 C6 0(2) . . . . ? C4 C5 C6 C7 176.8(15) . . . . ? C4 C5 C6 C1 1(2) . . . . ? N1 C1 C6 C7 2.3(17) . . . . ? C2 C1 C6 C7 -179.5(12) . . . . ? N1 C1 C6 C5 178.9(12) . . . . ? C2 C1 C6 C5 -2.9(18) . . . . ? O8 N3 O6 Eu2 -171.2(13) . . . . ? O7 N3 O6 Eu2 8.4(12) . . . . ? O2 Eu2 O6 N3 78.3(8) . . . . ? O3 Eu2 O6 N3 -89.2(8) . . . . ? O7 Eu2 O6 N3 -5.0(7) . . . . ? O10 Eu2 O6 N3 -128.5(9) . . . . ? O12 Eu2 O6 N3 29.4(10) . . . . ? O9 Eu2 O6 N3 145.6(8) . . . . ? O13 Eu2 O6 N3 -30.7(9) . . . . ? N1 Eu2 O6 N3 -153.6(9) . . . . ? O1 Eu2 O6 N3 142.4(9) . . . . ? O8 N3 O7 Eu2 171.1(13) . . . . ? O6 N3 O7 Eu2 -8.5(12) . . . . ? O2 Eu2 O7 N3 -77.9(8) . . . . ? O3 Eu2 O7 N3 91.3(8) . . . . ? O10 Eu2 O7 N3 143.8(7) . . . . ? O6 Eu2 O7 N3 5.0(7) . . . . ? O12 Eu2 O7 N3 -151.6(8) . . . . ? O9 Eu2 O7 N3 -110.8(11) . . . . ? O13 Eu2 O7 N3 160.9(8) . . . . ? N1 Eu2 O7 N3 40.8(9) . . . . ? O1 Eu2 O7 N3 -28.9(8) . . . . ? C5 C6 C7 C8 178.8(16) . . . . ? C1 C6 C7 C8 -5(2) . . . . ? C6 C7 C8 C9 6(2) . . . . ? O11 N4 O9 Eu2 171.3(13) . . . . ? O10 N4 O9 Eu2 -7.4(12) . . . . ? O2 Eu2 O9 N4 -153.3(8) . . . . ? O3 Eu2 O9 N4 33.0(9) . . . . ? O7 Eu2 O9 N4 -121.4(10) . . . . ? O10 Eu2 O9 N4 4.4(7) . . . . ? O6 Eu2 O9 N4 142.9(8) . . . . ? O12 Eu2 O9 N4 -78.3(8) . . . . ? O13 Eu2 O9 N4 -40.5(8) . . . . ? N1 Eu2 O9 N4 83.4(8) . . . . ? O1 Eu2 O9 N4 146.2(8) . . . . ? C1 N1 C9 C8 1.1(18) . . . . ? Eu2 N1 C9 C8 171.0(10) . . . . ? C1 N1 C9 C18 176.0(11) . . . . ? Eu2 N1 C9 C18 -14.1(15) . . . . ? C7 C8 C9 N1 -3(2) . . . . ? C7 C8 C9 C18 -178.2(14) . . . . ? O11 N4 O10 Eu2 -171.2(14) . . . . ? O9 N4 O10 Eu2 7.5(12) . . . . ? O2 Eu2 O10 N4 25.6(9) . . . . ? O3 Eu2 O10 N4 -159.3(8) . . . . ? O7 Eu2 O10 N4 147.0(7) . . . . ? O6 Eu2 O10 N4 -119.2(9) . . . . ? O12 Eu2 O10 N4 76.8(8) . . . . ? O9 Eu2 O10 N4 -4.4(7) . . . . ? O13 Eu2 O10 N4 129.8(8) . . . . ? N1 Eu2 O10 N4 -93.9(8) . . . . ? O1 Eu2 O10 N4 -39.9(8) . . . . ? C2 O1 C10 C11 -178.9(10) . . . . ? Eu2 O1 C10 C11 14.2(13) . . . . ? Eu2 O2 C11 N2 -178.6(8) . . . . ? Eu2 O2 C11 C10 -0.9(17) . . . . ? C12 N2 C11 O2 -175.3(11) . . . . ? C15 N2 C11 O2 -1.6(18) . . . . ? C12 N2 C11 C10 7.1(18) . . . . ? C15 N2 C11 C10 -179.2(11) . . . . ? O1 C10 C11 O2 -9.2(15) . . . . ? O1 C10 C11 N2 168.6(11) . . . . ? O14 N5 O12 Eu2 -174.0(11) . . . . ? O13 N5 O12 Eu2 4.2(12) . . . . ? O2 Eu2 O12 N5 -142.3(8) . . . . ? O3 Eu2 O12 N5 11.4(9) . . . . ? O7 Eu2 O12 N5 -67.0(8) . . . . ? O10 Eu2 O12 N5 75.5(8) . . . . ? O6 Eu2 O12 N5 -92.9(8) . . . . ? O9 Eu2 O12 N5 128.1(8) . . . . ? O13 Eu2 O12 N5 -2.4(7) . . . . ? N1 Eu2 O12 N5 92.6(10) . . . . ? O1 Eu2 O12 N5 174.9(7) . . . . ? C11 N2 C12 C14 -133.7(13) . . . . ? C15 N2 C12 C14 52.4(16) . . . . ? C11 N2 C12 C13 101.3(14) . . . . ? C15 N2 C12 C13 -72.6(14) . . . . ? O14 N5 O13 Eu2 174.0(11) . . . . ? O12 N5 O13 Eu2 -4.2(12) . . . . ? O2 Eu2 O13 N5 44.9(8) . . . . ? O3 Eu2 O13 N5 -164.1(8) . . . . ? O7 Eu2 O13 N5 109.4(8) . . . . ? O10 Eu2 O13 N5 -82.2(7) . . . . ? O6 Eu2 O13 N5 130.3(7) . . . . ? O12 Eu2 O13 N5 2.5(7) . . . . ? O9 Eu2 O13 N5 -47.1(8) . . . . ? N1 Eu2 O13 N5 -137.1(7) . . . . ? O1 Eu2 O13 N5 -11(2) . . . . ? C11 N2 C15 C17 66.5(16) . . . . ? C12 N2 C15 C17 -119.6(13) . . . . ? C11 N2 C15 C16 -60.9(16) . . . . ? C12 N2 C15 C16 113.0(13) . . . . ? C20 O4 C18 O3 22.4(18) . . . . ? C20 O4 C18 C9 143.7(15) . . . . ? C19 O3 C18 O4 -34.4(14) . . . . ? Eu2 O3 C18 O4 138.8(9) . . . . ? C19 O3 C18 C9 -155.2(12) . . . . ? Eu2 O3 C18 C9 18.0(16) . . . . ? N1 C9 C18 O4 -118.8(13) . . . . ? C8 C9 C18 O4 56.1(17) . . . . ? N1 C9 C18 O3 -1.2(18) . . . . ? C8 C9 C18 O3 173.7(12) . . . . ? C18 O3 C19 C20 32.2(15) . . . . ? Eu2 O3 C19 C20 -140.4(12) . . . . ? C18 O4 C20 C19 -2(2) . . . . ? C18 O4 C20 C21 -118.0(14) . . . . ? O3 C19 C20 O4 -18.3(18) . . . . ? O3 C19 C20 C21 93.8(16) . . . . ? C22 O5 C21 C20 -169.0(19) . . . . ? O4 C20 C21 O5 -175.7(14) . . . . ? C19 C20 C21 O5 73.5(19) . . . . ? C21 O5 C22 C23 -170(2) . . . . ? O5 C22 C23 C24 9(5) . . . . ? _diffrn_measured_fraction_theta_max 0.999 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 0.999 _refine_diff_density_max 2.478 _refine_diff_density_min -1.041 _refine_diff_density_rms 0.167