# Electronic Supplementary Material (ESI) for Chemical Communications # This journal is © The Royal Society of Chemistry 2013 ####################################################################### # # 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_p _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C25 H36 Eu N O12' _chemical_formula_weight 694.51 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 'P2(1)/n ' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, y+1/2, -z+1/2' '-x, -y, -z' 'x-1/2, -y-1/2, z-1/2' _cell_length_a 8.9760(7) _cell_length_b 25.7636(19) _cell_length_c 11.8280(9) _cell_angle_alpha 90.00 _cell_angle_beta 90.3230(10) _cell_angle_gamma 90.00 _cell_volume 2735.2(4) _cell_formula_units_Z 4 _cell_measurement_temperature 298(2) _cell_measurement_reflns_used 7946 _cell_measurement_theta_min 2.40 _cell_measurement_theta_max 27.57 _exptl_crystal_description block _exptl_crystal_colour yellowish _exptl_crystal_size_max 0.20 _exptl_crystal_size_mid 0.20 _exptl_crystal_size_min 0.18 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.687 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1408 _exptl_absorpt_coefficient_mu 2.357 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.6500 _exptl_absorpt_correction_T_max 0.6763 _exptl_absorpt_process_details SADABS _exptl_special_details ; ? ; _diffrn_ambient_temperature 298(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 ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 13412 _diffrn_reflns_av_R_equivalents 0.0530 _diffrn_reflns_av_sigmaI/netI 0.0407 _diffrn_reflns_limit_h_min -10 _diffrn_reflns_limit_h_max 10 _diffrn_reflns_limit_k_min -21 _diffrn_reflns_limit_k_max 30 _diffrn_reflns_limit_l_min -14 _diffrn_reflns_limit_l_max 12 _diffrn_reflns_theta_min 1.89 _diffrn_reflns_theta_max 25.00 _reflns_number_total 4808 _reflns_number_gt 4334 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'APEX2 (Bruker,2005)' _computing_cell_refinement 'APEX2 (Bruker,2005)' _computing_data_reduction 'SAINT (Bruker, 2005)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'DIAMOND (Brandenburg, 2008)' _computing_publication_material 'publCIF (Westrip, 2010)' _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^)+(0.0582P)^2^+3.4436P] 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 4808 _refine_ls_number_parameters 350 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0414 _refine_ls_R_factor_gt 0.0370 _refine_ls_wR_factor_ref 0.0996 _refine_ls_wR_factor_gt 0.0966 _refine_ls_goodness_of_fit_ref 1.056 _refine_ls_restrained_S_all 1.056 _refine_ls_shift/su_max 0.003 _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 0.98861(2) 0.377843(7) 0.990286(16) 0.01852(8) Uani 1 1 d . . . C5 C 1.5091(4) 0.32678(16) 0.5448(4) 0.0223(9) Uani 1 1 d . . . O10 O 1.0656(3) 0.45872(10) 0.9077(3) 0.0271(7) Uani 1 1 d . . . H10A H 1.1033 0.4790 0.9589 0.041 Uiso 1 1 d R . . H10B H 0.9899 0.4743 0.8767 0.041 Uiso 1 1 d R . . O3 O 1.5357(4) 0.20038(11) 0.6096(3) 0.0323(7) Uani 1 1 d . . . O2 O 1.2381(3) 0.34491(12) 0.9137(3) 0.0317(7) Uani 1 1 d . . . C6 C 1.4781(5) 0.37741(14) 0.5805(4) 0.0191(9) Uani 1 1 d . . . C13 C 1.5266(4) 0.42761(14) 0.3946(3) 0.0194(8) Uani 1 1 d . . . O5 O 1.7640(4) 0.36517(12) 0.1015(3) 0.0444(10) Uani 1 1 d . . . O6 O 1.8133(3) 0.44628(11) 0.0721(3) 0.0311(7) Uani 1 1 d . . . O1 O 1.0629(3) 0.35972(12) 0.7898(3) 0.0319(7) Uani 1 1 d . . . C22 C 1.7390(5) 0.41261(16) 0.1214(3) 0.0225(9) Uani 1 1 d . . . C4 C 1.4289(5) 0.28457(15) 0.5914(4) 0.0235(9) Uani 1 1 d . . . O4 O 1.4023(4) 0.21484(11) 0.4584(3) 0.0319(7) Uani 1 1 d . . . O8 O 1.1487(5) 0.49203(13) 0.1991(4) 0.0533(11) Uani 1 1 d . . . C16 C 1.4733(5) 0.43208(15) 0.1590(3) 0.0225(9) Uani 1 1 d . . . C23 C 1.2019(5) 0.44796(16) 0.1871(4) 0.0261(10) Uani 1 1 d . . . C17 C 1.3561(5) 0.43806(15) 0.2354(4) 0.0223(9) Uani 1 1 d . . . C14 C 1.6453(4) 0.42435(15) 0.3190(4) 0.0199(8) Uani 1 1 d . . . C1 C 1.1965(5) 0.34988(15) 0.8132(4) 0.0232(9) Uani 1 1 d . . . C15 C 1.6152(4) 0.42454(15) 0.2019(3) 0.0205(9) Uani 1 1 d . . . C18 C 1.3814(4) 0.43588(15) 0.3521(4) 0.0210(9) Uani 1 1 d . . . C11 C 1.4572(5) 0.23033(15) 0.5499(4) 0.0235(9) Uani 1 1 d . . . C2 C 1.3057(4) 0.34252(15) 0.7178(4) 0.0229(9) Uani 1 1 d . . . C21 C 1.4452(5) 0.4347(2) 0.0338(4) 0.0334(11) Uani 1 1 d . . . H21A H 1.3924 0.4042 0.0099 0.050 Uiso 1 1 calc R . . H21B H 1.5386 0.4367 -0.0051 0.050 Uiso 1 1 calc R . . H21C H 1.3868 0.4649 0.0167 0.050 Uiso 1 1 calc R . . C20 C 1.8073(5) 0.42173(19) 0.3550(4) 0.0324(11) Uani 1 1 d . . . H20A H 1.8201 0.4396 0.4256 0.049 Uiso 1 1 calc R . . H20B H 1.8680 0.4379 0.2985 0.049 Uiso 1 1 calc R . . H20C H 1.8364 0.3861 0.3636 0.049 Uiso 1 1 calc R . . C7 C 1.3824(5) 0.38509(15) 0.6722(4) 0.0210(9) Uani 1 1 d . . . C19 C 1.2510(5) 0.44411(18) 0.4312(4) 0.0309(10) Uani 1 1 d . . . H19A H 1.2527 0.4180 0.4892 0.046 Uiso 1 1 calc R . . H19B H 1.1594 0.4417 0.3893 0.046 Uiso 1 1 calc R . . H19C H 1.2584 0.4778 0.4653 0.046 Uiso 1 1 calc R . . O9 O 0.7774(4) 0.39229(17) 0.8560(3) 0.0531(10) Uani 1 1 d . . . C3 C 1.3243(5) 0.29216(15) 0.6756(4) 0.0249(9) Uani 1 1 d . . . C10 C 1.6317(5) 0.31512(17) 0.4628(4) 0.0369(12) Uani 1 1 d . . . H10C H 1.6011 0.3253 0.3881 0.055 Uiso 1 1 calc R . . H10D H 1.6526 0.2786 0.4637 0.055 Uiso 1 1 calc R . . H10E H 1.7196 0.3340 0.4842 0.055 Uiso 1 1 calc R . . C8 C 1.3581(6) 0.43793(15) 0.7248(4) 0.0321(11) Uani 1 1 d . . . H8A H 1.4526 0.4531 0.7441 0.048 Uiso 1 1 calc R . . H8B H 1.2991 0.4343 0.7918 0.048 Uiso 1 1 calc R . . H8C H 1.3070 0.4600 0.6719 0.048 Uiso 1 1 calc R . . C9 C 1.2384(6) 0.24759(17) 0.7236(5) 0.0500(15) Uani 1 1 d . . . H9C H 1.1717 0.2601 0.7806 0.075 Uiso 1 1 calc R . . H9D H 1.3063 0.2230 0.7566 0.075 Uiso 1 1 calc R . . H9E H 1.1822 0.2311 0.6645 0.075 Uiso 1 1 calc R . . C12 C 1.5530(5) 0.42316(16) 0.5225(3) 0.0212(9) Uani 1 1 d . . . H12A H 1.6595 0.4208 0.5360 0.025 Uiso 1 1 calc R . . H12B H 1.5183 0.4549 0.5578 0.025 Uiso 1 1 calc R . . O7 O 1.1378(3) 0.41085(12) 0.1368(3) 0.0300(7) Uani 1 1 d . . . O1W O 1.5452(6) 0.3083(2) 0.9384(6) 0.1013(19) Uani 1 1 d . . . N1 N 1.6933(9) 0.2306(3) 0.7994(6) 0.103(2) Uani 1 1 d . . . H1A H 1.7148 0.2591 0.8405 0.124 Uiso 1 1 calc R . . H1B H 1.6208 0.2386 0.7495 0.124 Uiso 1 1 calc R . . C25 C 1.6448(12) 0.1870(4) 0.8748(9) 0.114(3) Uiso 1 1 d . . . H25A H 1.6281 0.1564 0.8302 0.172 Uiso 1 1 calc R . . H25B H 1.5542 0.1965 0.9123 0.172 Uiso 1 1 calc R . . H25C H 1.7210 0.1802 0.9302 0.172 Uiso 1 1 calc R . . C24 C 1.8300(18) 0.2114(6) 0.7389(15) 0.207(7) Uiso 1 1 d . . . H24A H 1.8005 0.1901 0.6761 0.310 Uiso 1 1 calc R . . H24B H 1.8902 0.1914 0.7902 0.310 Uiso 1 1 calc R . . H24C H 1.8864 0.2405 0.7120 0.310 Uiso 1 1 calc R . . O2W O 0.8963(9) 0.4218(3) 0.6431(5) 0.137(3) Uani 1 1 d . . . H2WA H 0.9468 0.4004 0.6824 0.164 Uiso 1 1 d R . . H2WB H 0.8778 0.4482 0.6839 0.164 Uiso 1 1 d 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 Eu1 0.02157(13) 0.01332(13) 0.02076(13) 0.00048(7) 0.00839(9) 0.00065(7) C5 0.026(2) 0.021(2) 0.020(2) 0.0026(17) 0.0095(17) -0.0030(16) O10 0.0318(16) 0.0142(14) 0.0354(17) 0.0035(13) 0.0046(14) 0.0010(12) O3 0.0394(18) 0.0199(15) 0.0377(18) -0.0055(13) 0.0007(15) 0.0070(13) O2 0.0359(17) 0.0351(18) 0.0241(17) -0.0015(13) 0.0110(14) 0.0048(14) C6 0.022(2) 0.016(2) 0.020(2) 0.0011(15) 0.0069(17) 0.0017(15) C13 0.026(2) 0.0102(18) 0.022(2) -0.0001(15) 0.0056(17) -0.0004(15) O5 0.056(2) 0.0172(16) 0.060(2) 0.0057(16) 0.0389(19) 0.0074(15) O6 0.0317(16) 0.0194(15) 0.0423(19) -0.0028(13) 0.0204(15) -0.0064(13) O1 0.0303(17) 0.0349(17) 0.0307(17) -0.0020(14) 0.0096(14) 0.0034(14) C22 0.024(2) 0.021(2) 0.022(2) 0.0010(17) 0.0067(17) 0.0009(17) C4 0.030(2) 0.0135(19) 0.027(2) -0.0010(17) 0.0078(19) 0.0002(17) O4 0.0475(19) 0.0207(15) 0.0275(17) -0.0045(13) 0.0036(15) 0.0049(14) O8 0.052(2) 0.033(2) 0.075(3) -0.0116(18) -0.026(2) 0.0180(16) C16 0.029(2) 0.016(2) 0.023(2) 0.0016(16) 0.0048(18) -0.0011(16) C23 0.028(2) 0.024(2) 0.027(2) 0.0028(18) 0.0063(18) 0.0052(18) C17 0.024(2) 0.015(2) 0.028(2) -0.0013(17) 0.0038(18) 0.0004(16) C14 0.0192(19) 0.0131(19) 0.028(2) 0.0017(16) 0.0065(17) -0.0006(15) C1 0.032(2) 0.0105(19) 0.028(2) -0.0039(16) 0.0120(19) -0.0022(16) C15 0.024(2) 0.0131(19) 0.025(2) -0.0005(16) 0.0086(17) -0.0011(16) C18 0.022(2) 0.0151(19) 0.026(2) -0.0024(16) 0.0077(17) -0.0005(15) C11 0.026(2) 0.018(2) 0.027(2) -0.0006(17) 0.0172(19) -0.0005(17) C2 0.025(2) 0.018(2) 0.026(2) 0.0023(17) 0.0106(18) 0.0005(16) C21 0.034(2) 0.043(3) 0.023(2) 0.000(2) 0.003(2) -0.001(2) C20 0.025(2) 0.043(3) 0.029(2) 0.005(2) 0.0059(19) 0.000(2) C7 0.030(2) 0.0127(19) 0.020(2) -0.0025(15) 0.0050(18) 0.0005(16) C19 0.025(2) 0.035(3) 0.033(3) 0.000(2) 0.009(2) 0.0063(19) O9 0.041(2) 0.078(3) 0.040(2) -0.005(2) -0.0006(17) 0.015(2) C3 0.034(2) 0.015(2) 0.027(2) -0.0004(17) 0.0152(19) -0.0031(17) C10 0.045(3) 0.019(2) 0.048(3) 0.000(2) 0.030(2) 0.003(2) C8 0.053(3) 0.013(2) 0.031(2) -0.0043(18) 0.019(2) -0.0043(19) C9 0.062(3) 0.020(2) 0.069(4) -0.006(2) 0.046(3) -0.009(2) C12 0.024(2) 0.020(2) 0.020(2) -0.0006(16) 0.0079(17) -0.0014(17) O7 0.0274(16) 0.0305(17) 0.0320(17) -0.0022(14) 0.0014(14) -0.0044(13) O1W 0.068(3) 0.111(4) 0.125(5) -0.040(4) -0.022(3) 0.026(3) N1 0.125(6) 0.092(5) 0.092(5) -0.038(4) -0.012(4) -0.016(5) O2W 0.191(7) 0.121(5) 0.097(5) -0.004(4) -0.069(5) 0.029(5) _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 O7 2.343(3) 1_556 ? Eu1 O10 2.405(3) . ? Eu1 O5 2.436(3) 1_456 ? Eu1 O9 2.494(4) . ? Eu1 O3 2.495(3) 4_566 ? Eu1 O1 2.511(3) . ? Eu1 O4 2.538(3) 4_566 ? Eu1 O6 2.557(3) 1_456 ? Eu1 O2 2.565(3) . ? Eu1 C22 2.875(4) 1_456 ? Eu1 C11 2.889(4) 4_566 ? Eu1 C1 2.904(4) . ? C5 C6 1.399(5) . ? C5 C4 1.417(6) . ? C5 C10 1.501(6) . ? O3 C11 1.259(5) . ? O3 Eu1 2.495(3) 4_665 ? O2 C1 1.250(5) . ? C6 C7 1.402(6) . ? C6 C12 1.522(5) . ? C13 C14 1.397(6) . ? C13 C18 1.411(6) . ? C13 C12 1.534(5) . ? O5 C22 1.265(5) . ? O5 Eu1 2.436(3) 1_654 ? O6 C22 1.241(5) . ? O6 Eu1 2.557(3) 1_654 ? O1 C1 1.256(5) . ? C22 C15 1.499(5) . ? C22 Eu1 2.875(4) 1_654 ? C4 C3 1.387(6) . ? C4 C11 1.503(5) . ? O4 C11 1.252(5) . ? O4 Eu1 2.538(3) 4_665 ? O8 C23 1.240(5) . ? C16 C15 1.383(6) . ? C16 C17 1.399(6) . ? C16 C21 1.501(6) . ? C23 O7 1.263(5) . ? C23 C17 1.515(6) . ? C17 C18 1.399(6) . ? C14 C15 1.410(6) . ? C14 C20 1.514(6) . ? C1 C2 1.510(6) . ? C18 C19 1.517(6) . ? C11 Eu1 2.889(4) 4_665 ? C2 C3 1.401(6) . ? C2 C7 1.404(6) . ? C7 C8 1.513(5) . ? C3 C9 1.497(6) . ? O7 Eu1 2.343(3) 1_554 ? N1 C25 1.501(11) . ? N1 C24 1.507(16) . ? 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 O7 Eu1 O10 79.73(11) 1_556 . ? O7 Eu1 O5 96.94(12) 1_556 1_456 ? O10 Eu1 O5 125.19(10) . 1_456 ? O7 Eu1 O9 147.75(12) 1_556 . ? O10 Eu1 O9 80.27(13) . . ? O5 Eu1 O9 74.65(14) 1_456 . ? O7 Eu1 O3 77.33(10) 1_556 4_566 ? O10 Eu1 O3 151.84(10) . 4_566 ? O5 Eu1 O3 74.01(11) 1_456 4_566 ? O9 Eu1 O3 127.34(13) . 4_566 ? O7 Eu1 O1 127.74(10) 1_556 . ? O10 Eu1 O1 72.48(10) . . ? O5 Eu1 O1 135.25(13) 1_456 . ? O9 Eu1 O1 68.36(11) . . ? O3 Eu1 O1 109.81(10) 4_566 . ? O7 Eu1 O4 128.61(10) 1_556 4_566 ? O10 Eu1 O4 147.47(10) . 4_566 ? O5 Eu1 O4 72.61(11) 1_456 4_566 ? O9 Eu1 O4 79.36(13) . 4_566 ? O3 Eu1 O4 51.30(10) 4_566 4_566 ? O1 Eu1 O4 76.53(10) . 4_566 ? O7 Eu1 O6 79.64(11) 1_556 1_456 ? O10 Eu1 O6 74.64(9) . 1_456 ? O5 Eu1 O6 51.31(10) 1_456 1_456 ? O9 Eu1 O6 70.80(12) . 1_456 ? O3 Eu1 O6 116.46(10) 4_566 1_456 ? O1 Eu1 O6 130.77(10) . 1_456 ? O4 Eu1 O6 121.13(10) 4_566 1_456 ? O7 Eu1 O2 83.37(10) 1_556 . ? O10 Eu1 O2 83.67(10) . . ? O5 Eu1 O2 150.87(10) 1_456 . ? O9 Eu1 O2 119.12(11) . . ? O3 Eu1 O2 77.70(10) 4_566 . ? O1 Eu1 O2 50.80(10) . . ? O4 Eu1 O2 84.43(10) 4_566 . ? O6 Eu1 O2 154.44(10) 1_456 . ? O7 Eu1 C22 86.09(11) 1_556 1_456 ? O10 Eu1 C22 100.12(11) . 1_456 ? O5 Eu1 C22 25.90(11) 1_456 1_456 ? O9 Eu1 C22 72.86(12) . 1_456 ? O3 Eu1 C22 94.39(11) 4_566 1_456 ? O1 Eu1 C22 141.20(11) . 1_456 ? O4 Eu1 C22 97.76(11) 4_566 1_456 ? O6 Eu1 C22 25.57(10) 1_456 1_456 ? O2 Eu1 C22 167.99(11) . 1_456 ? O7 Eu1 C11 103.05(12) 1_556 4_566 ? O10 Eu1 C11 164.54(10) . 4_566 ? O5 Eu1 C11 69.93(11) 1_456 4_566 ? O9 Eu1 C11 102.98(14) . 4_566 ? O3 Eu1 C11 25.74(11) 4_566 4_566 ? O1 Eu1 C11 94.46(11) . 4_566 ? O4 Eu1 C11 25.65(11) 4_566 4_566 ? O6 Eu1 C11 120.78(10) 1_456 4_566 ? O2 Eu1 C11 81.58(10) . 4_566 ? C22 Eu1 C11 95.26(11) 1_456 4_566 ? O7 Eu1 C1 104.85(11) 1_556 . ? O10 Eu1 C1 74.61(10) . . ? O5 Eu1 C1 153.33(12) 1_456 . ? O9 Eu1 C1 93.85(12) . . ? O3 Eu1 C1 95.74(11) 4_566 . ? O1 Eu1 C1 25.52(11) . . ? O4 Eu1 C1 81.74(10) 4_566 . ? O6 Eu1 C1 147.51(10) 1_456 . ? O2 Eu1 C1 25.48(11) . . ? C22 Eu1 C1 166.49(12) 1_456 . ? C11 Eu1 C1 90.03(11) 4_566 . ? C6 C5 C4 119.8(4) . . ? C6 C5 C10 121.9(4) . . ? C4 C5 C10 118.2(4) . . ? C11 O3 Eu1 94.9(3) . 4_665 ? C1 O2 Eu1 92.6(3) . . ? C5 C6 C7 119.2(3) . . ? C5 C6 C12 119.8(4) . . ? C7 C6 C12 120.9(3) . . ? C14 C13 C18 119.2(4) . . ? C14 C13 C12 120.8(4) . . ? C18 C13 C12 120.0(3) . . ? C22 O5 Eu1 96.8(3) . 1_654 ? C22 O6 Eu1 91.7(2) . 1_654 ? C1 O1 Eu1 95.0(3) . . ? O6 C22 O5 119.4(4) . . ? O6 C22 C15 123.9(4) . . ? O5 C22 C15 116.7(3) . . ? O6 C22 Eu1 62.7(2) . 1_654 ? O5 C22 Eu1 57.3(2) . 1_654 ? C15 C22 Eu1 171.5(3) . 1_654 ? C3 C4 C5 121.2(4) . . ? C3 C4 C11 118.8(4) . . ? C5 C4 C11 120.0(4) . . ? C11 O4 Eu1 93.0(2) . 4_665 ? C15 C16 C17 118.2(4) . . ? C15 C16 C21 121.2(4) . . ? C17 C16 C21 120.6(4) . . ? O8 C23 O7 124.9(4) . . ? O8 C23 C17 117.5(4) . . ? O7 C23 C17 117.6(4) . . ? C16 C17 C18 121.0(4) . . ? C16 C17 C23 117.6(4) . . ? C18 C17 C23 121.4(4) . . ? C13 C14 C15 119.1(4) . . ? C13 C14 C20 123.9(4) . . ? C15 C14 C20 117.0(4) . . ? O2 C1 O1 120.7(4) . . ? O2 C1 C2 120.4(4) . . ? O1 C1 C2 118.9(4) . . ? O2 C1 Eu1 61.9(2) . . ? O1 C1 Eu1 59.5(2) . . ? C2 C1 Eu1 172.8(3) . . ? C16 C15 C14 122.2(4) . . ? C16 C15 C22 118.7(4) . . ? C14 C15 C22 119.0(4) . . ? C17 C18 C13 120.1(4) . . ? C17 C18 C19 118.8(4) . . ? C13 C18 C19 121.1(4) . . ? O4 C11 O3 120.4(4) . . ? O4 C11 C4 120.8(4) . . ? O3 C11 C4 118.8(4) . . ? O4 C11 Eu1 61.3(2) . 4_665 ? O3 C11 Eu1 59.4(2) . 4_665 ? C4 C11 Eu1 173.4(3) . 4_665 ? C3 C2 C7 121.8(4) . . ? C3 C2 C1 117.5(3) . . ? C7 C2 C1 120.7(4) . . ? C6 C7 C2 119.4(3) . . ? C6 C7 C8 122.4(4) . . ? C2 C7 C8 118.2(4) . . ? C4 C3 C2 118.0(4) . . ? C4 C3 C9 121.1(4) . . ? C2 C3 C9 120.9(4) . . ? C6 C12 C13 115.9(3) . . ? C23 O7 Eu1 151.7(3) . 1_554 ? C25 N1 C24 106.0(9) . . ? _diffrn_measured_fraction_theta_max 0.997 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 0.997 _refine_diff_density_max 1.773 _refine_diff_density_min -0.984 _refine_diff_density_rms 0.136 _database_code_depnum_ccdc_archive 'CCDC 942215'