# Supplementary Material (ESI) for Chemical Communications # This journal is (c) The Royal Society of Chemistry 2011 data_global _journal_name_full Chem.Commun. _journal_coden_Cambridge 0182 _publ_contact_author_name 'Davide Bonifazi' _publ_contact_author_address ; Rue de Bruxelles 61 NAMUR B-5000 ; _publ_contact_author_email davide.bonifazi@fundp.ac.be loop_ _publ_author_name L.Maggini H.Traboulsi K.Yoosaf J.Mohanraj J.Wouters ; O.Pietraszkiewicz ; M.Pietraszkiewicz N.Armaroli D.Bonifazi data_bn_dln-ipc022-eur _database_code_depnum_ccdc_archive 'CCDC 787011' #TrackingRef 'bn-dln-ipc022-eur.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C56 H32 Eu F12 O8, C8 H20 N' _chemical_formula_sum 'C64 H52 Eu F12 N O8' _chemical_formula_weight 1343.03 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' F F 0.0171 0.0103 '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 'P 21' _symmetry_space_group_name_Hall 'P 2yb' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z' _cell_length_a 12.1252(10) _cell_length_b 21.996(2) _cell_length_c 12.8415(10) _cell_angle_alpha 90.00 _cell_angle_beta 117.955(10) _cell_angle_gamma 90.00 _cell_volume 3025.3(4) _cell_formula_units_Z 2 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 3975 _cell_measurement_theta_min 3.3018 _cell_measurement_theta_max 32.6139 _exptl_crystal_description plaquet _exptl_crystal_colour colorless _exptl_crystal_size_max 0.32 _exptl_crystal_size_mid 0.10 _exptl_crystal_size_min 0.02 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.474 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1356 _exptl_absorpt_coefficient_mu 1.128 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.7141 _exptl_absorpt_correction_T_max 0.9778 _exptl_absorpt_process_details ; CrysAlisPro, Oxford Diffraction Ltd., Version 1.171.33.55 (release 05-01-2010 CrysAlis171 .NET) (compiled Jan 5 2010,16:28:46) Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm. ; _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 'Xcalibur, Ruby, Gemini ultra' _diffrn_measurement_method '\w scans' _diffrn_detector_area_resol_mean 10.3712 _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 19343 _diffrn_reflns_av_R_equivalents 0.0521 _diffrn_reflns_av_sigmaI/netI 0.2738 _diffrn_reflns_limit_h_min -18 _diffrn_reflns_limit_h_max 17 _diffrn_reflns_limit_k_min -32 _diffrn_reflns_limit_k_max 33 _diffrn_reflns_limit_l_min -18 _diffrn_reflns_limit_l_max 18 _diffrn_reflns_theta_min 3.31 _diffrn_reflns_theta_max 32.69 _reflns_number_total 14328 _reflns_number_gt 4801 _reflns_threshold_expression >2sigma(I) _computing_data_collection ; CrysAlisPro, Oxford Diffraction Ltd., Version 1.171.33.55 (release 05-01-2010 CrysAlis171 .NET) (compiled Jan 5 2010,16:28:46) ; _computing_cell_refinement ; CrysAlisPro, Oxford Diffraction Ltd., Version 1.171.33.55 (release 05-01-2010 CrysAlis171 .NET) (compiled Jan 5 2010,16:28:46) ; _computing_data_reduction ; CrysAlisPro, Oxford Diffraction Ltd., Version 1.171.33.55 (release 05-01-2010 CrysAlis171 .NET) (compiled Jan 5 2010,16:28:46) ; _computing_structure_solution shelxs86 _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^)+(0.1316P)^2^+0.0000P] 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_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _refine_ls_abs_structure_Flack -0.01(2) _refine_ls_number_reflns 14328 _refine_ls_number_parameters 515 _refine_ls_number_restraints 73 _refine_ls_R_factor_all 0.2155 _refine_ls_R_factor_gt 0.0903 _refine_ls_wR_factor_ref 0.2500 _refine_ls_wR_factor_gt 0.2174 _refine_ls_goodness_of_fit_ref 0.818 _refine_ls_restrained_S_all 0.820 _refine_ls_shift/su_max 0.081 _refine_ls_shift/su_mean 0.006 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 0.47167(5) 0.23426(13) 0.15898(5) 0.0478(2) Uani 1 1 d . A . C1 C 0.31311(5) 0.26117(13) 0.44884(5) 0.074(5) Uani 1 1 d R . . H1 H 0.3930 0.2687 0.4589 0.088 Uiso 1 1 calc R . . C2 C 0.21863(5) 0.24367(13) 0.33913(5) 0.066(4) Uani 1 1 d R . . C3 C 0.09925(5) 0.23239(13) 0.32409(5) 0.096(6) Uani 1 1 d R . . H3 H 0.0360 0.2207 0.2507 0.115 Uiso 1 1 calc R . . C4 C 0.07435(5) 0.23860(13) 0.41876(5) 0.101(5) Uani 1 1 d R . . H4 H -0.0055 0.2310 0.4087 0.121 Uiso 1 1 calc R . . C5 C 0.16882(5) 0.25609(13) 0.52847(5) 0.072(5) Uani 1 1 d R . . C6 C 0.28820(5) 0.26738(13) 0.54352(5) 0.060(4) Uani 1 1 d R . . C7 C 0.38268(5) 0.28487(13) 0.65323(5) 0.079(5) Uani 1 1 d R . . H7 H 0.4625 0.2924 0.6633 0.095 Uiso 1 1 calc R . . C8 C 0.35777(5) 0.29108(13) 0.74790(5) 0.110(8) Uani 1 1 d R . . H8 H 0.4210 0.3028 0.8213 0.132 Uiso 1 1 calc R . . C9 C 0.23839(5) 0.27980(13) 0.73286(5) 0.089(6) Uani 1 1 d R . . H9 H 0.2217 0.2840 0.7962 0.107 Uiso 1 1 calc R . . C10 C 0.14392(5) 0.26230(13) 0.62315(5) 0.118(8) Uani 1 1 d R . . H10 H 0.0640 0.2548 0.6131 0.141 Uiso 1 1 calc R . . C11 C 0.2347(12) 0.2343(10) 0.2346(11) 0.064(4) Uani 1 1 d . . . C12 C 0.1413(12) 0.2243(9) 0.1176(10) 0.062(5) Uani 1 1 d . . . H12 H 0.0612 0.2166 0.1067 0.074 Uiso 1 1 calc R . . C13 C 0.1565(12) 0.2249(7) 0.0189(11) 0.046(4) Uani 1 1 d . A . C14 C 0.0327(11) 0.2199(6) -0.1044(11) 0.105(9) Uani 1 1 d D . . F1 F 0.046(2) 0.2262(11) -0.2011(17) 0.104(6) Uani 0.30 1 d PD A 1 F2 F -0.048(2) 0.2605(8) -0.107(2) 0.095(5) Uani 0.30 1 d PD A 1 F3 F -0.003(2) 0.1646(7) -0.100(2) 0.130(8) Uani 0.30 1 d PD A 1 F1' F -0.0712(11) 0.2064(8) -0.0960(13) 0.104(6) Uani 0.70 1 d PD A 2 F2' F 0.0517(10) 0.1745(8) -0.1609(11) 0.095(5) Uani 0.70 1 d PD A 2 F3' F 0.0096(17) 0.2706(7) -0.1657(17) 0.130(8) Uani 0.70 1 d PD A 2 C31 C 0.4551(6) 0.3745(3) 0.0353(7) 0.056(4) Uani 1 1 d . A . C21 C 0.2375(6) 0.4156(3) -0.0807(7) 0.102(4) Uani 1 1 d R . . H21 H 0.2039 0.3769 -0.0872 0.123 Uiso 1 1 calc R . . C22 C 0.3662(6) 0.4238(3) -0.0221(7) 0.057(2) Uani 1 1 d R . . C23 C 0.4164(6) 0.4816(3) -0.0125(7) 0.110(4) Uani 1 1 d R . . H23 H 0.5025 0.4871 0.0268 0.132 Uiso 1 1 calc R . . C24 C 0.3379(6) 0.5312(3) -0.0615(7) 0.122(5) Uani 1 1 d R . . H24 H 0.3715 0.5699 -0.0551 0.147 Uiso 1 1 calc R . . C25 C 0.2092(6) 0.5231(3) -0.1202(7) 0.084(3) Uani 1 1 d R . . C26 C 0.1590(6) 0.4652(3) -0.1298(7) 0.103(4) Uani 1 1 d R . . C27 C 0.0304(6) 0.4571(3) -0.1884(7) 0.124(5) Uani 1 1 d R . . H27 H -0.0032 0.4184 -0.1949 0.148 Uiso 1 1 calc R . . C28 C -0.0481(6) 0.5067(3) -0.2375(7) 0.147(6) Uani 1 1 d R . . H28 H -0.1342 0.5012 -0.2767 0.176 Uiso 1 1 calc R . . C29 C 0.0021(6) 0.5645(3) -0.2279(7) 0.176(8) Uani 1 1 d R . . H29 H -0.0505 0.5977 -0.2607 0.211 Uiso 1 1 calc R . . C30 C 0.1307(6) 0.5727(3) -0.1692(7) 0.152(7) Uani 1 1 d R . . H30 H 0.1643 0.6114 -0.1628 0.182 Uiso 1 1 calc R . . C32 C 0.5722(15) 0.3719(7) 0.0415(15) 0.068(4) Uani 1 1 d . . . H32 H 0.5988 0.4051 0.0143 0.082 Uiso 1 1 calc R . . C33 C 0.6520(12) 0.3225(8) 0.0861(15) 0.066(4) Uani 1 1 d . A . C34 C 0.7687(10) 0.3235(5) 0.0630(10) 0.099(7) Uani 1 1 d D . . F4 F 0.860(2) 0.2989(5) 0.1586(14) 0.169(10) Uani 0.50 1 d PD B 1 F5 F 0.8068(17) 0.3797(5) 0.0541(11) 0.109(6) Uani 0.50 1 d PD B 1 F6 F 0.755(2) 0.2930(9) -0.0311(14) 0.193(15) Uani 0.50 1 d PD B 1 F4' F 0.749(2) 0.3502(10) -0.0364(9) 0.169(10) Uani 0.50 1 d PD B 2 F5' F 0.8124(19) 0.2683(5) 0.0657(18) 0.109(6) Uani 0.50 1 d PD B 2 F6' F 0.8498(6) 0.3550(3) 0.1541(6) 0.193(15) Uani 0.50 1 d PD B 2 C41 C 0.7630(6) 0.0532(3) 0.3826(6) 0.102(4) Uani 1 1 d R . . H41 H 0.6933 0.0433 0.3121 0.123 Uiso 1 1 calc R . . C42 C 0.7817(6) 0.1128(3) 0.4231(6) 0.057(2) Uani 1 1 d R . . C43 C 0.8859(6) 0.1277(3) 0.5285(6) 0.110(4) Uani 1 1 d R . . H43 H 0.8984 0.1676 0.5555 0.132 Uiso 1 1 calc R . . C44 C 0.9715(6) 0.0829(3) 0.5934(6) 0.122(5) Uani 1 1 d R . . H44 H 1.0413 0.0928 0.6639 0.147 Uiso 1 1 calc R . . C45 C 0.9529(6) 0.0233(3) 0.5529(6) 0.084(3) Uani 1 1 d R . . C46 C 0.8486(6) 0.0084(3) 0.4475(6) 0.103(4) Uani 1 1 d R . . C49 C 0.8300(6) -0.0512(3) 0.4070(6) 0.176(8) Uani 1 1 d R . . H49 H 0.7603 -0.0612 0.3365 0.211 Uiso 1 1 calc R . . C48 C 0.9156(6) -0.0960(3) 0.4719(6) 0.147(6) Uani 1 1 d R . . H48 H 0.9031 -0.1359 0.4448 0.176 Uiso 1 1 calc R . . C47 C 1.0199(6) -0.0812(3) 0.5773(6) 0.124(5) Uani 1 1 d R . . H47 H 1.0771 -0.1112 0.6208 0.148 Uiso 1 1 calc R . . C50 C 1.0385(6) -0.0215(3) 0.6178(6) 0.152(7) Uani 1 1 d R . . H50 H 1.1082 -0.0116 0.6883 0.182 Uiso 1 1 calc R . . C51 C 0.7213(17) 0.1702(6) 0.384(2) 0.068(5) Uani 1 1 d . A . C52 C 0.7598(15) 0.2178(9) 0.4627(17) 0.080(8) Uani 1 1 d . . . H52 H 0.8352 0.2145 0.5316 0.096 Uiso 1 1 calc R . . C53 C 0.6935(17) 0.2679(11) 0.4439(18) 0.085(6) Uani 1 1 d . A . C54 C 0.7257(12) 0.3117(6) 0.5572(13) 0.173(12) Uiso 1 1 d D . . F7 F 0.6896(13) 0.3670(10) 0.510(2) 0.179(9) Uiso 0.50 1 d PD C 1 F8 F 0.8490(11) 0.3133(7) 0.6227(13) 0.090(4) Uiso 0.50 1 d PD C 1 F9 F 0.675(2) 0.3014(12) 0.627(2) 0.196(10) Uiso 0.50 1 d PD C 1 F7' F 0.7872(19) 0.2880(11) 0.6651(19) 0.179(9) Uiso 0.50 1 d PD C 2 F8' F 0.6241(11) 0.3381(9) 0.5459(17) 0.090(4) Uiso 0.50 1 d PD C 2 F9' F 0.7969(7) 0.3501(3) 0.5410(7) 0.196(10) Uiso 0.50 1 d PD C 2 C61 C 0.3735(7) 0.1162(3) -0.2883(7) 0.102(4) Uani 1 1 d R . . H61 H 0.2990 0.0985 -0.2999 0.123 Uiso 1 1 calc R . . C62 C 0.4542(7) 0.1413(3) -0.1794(7) 0.057(2) Uani 1 1 d R . . C63 C 0.5656(7) 0.1678(3) -0.1621(7) 0.110(4) Uani 1 1 d R . . H63 H 0.6196 0.1845 -0.0893 0.132 Uiso 1 1 calc R . . C64 C 0.5964(7) 0.1692(3) -0.2536(7) 0.122(5) Uani 1 1 d R . . H64 H 0.6709 0.1869 -0.2420 0.147 Uiso 1 1 calc R . . C65 C 0.5157(7) 0.1441(3) -0.3624(7) 0.084(3) Uani 1 1 d R . . C66 C 0.4043(7) 0.1177(3) -0.3798(7) 0.103(4) Uani 1 1 d R . . C67 C 0.3237(7) 0.0926(3) -0.4886(7) 0.124(5) Uani 1 1 d R . . H67 H 0.2491 0.0749 -0.5002 0.148 Uiso 1 1 calc R . . C68 C 0.3545(7) 0.0940(3) -0.5801(7) 0.147(6) Uani 1 1 d R . . H68 H 0.3005 0.0772 -0.6529 0.176 Uiso 1 1 calc R . . C69 C 0.4659(7) 0.1205(3) -0.5628(7) 0.176(8) Uani 1 1 d R . . H69 H 0.4865 0.1214 -0.6240 0.211 Uiso 1 1 calc R . . C70 C 0.5465(7) 0.1455(3) -0.4539(7) 0.152(7) Uani 1 1 d R . . H70 H 0.6211 0.1632 -0.4423 0.182 Uiso 1 1 calc R . . C71 C 0.4280(12) 0.1462(7) -0.0748(13) 0.063(4) Uani 1 1 d . A . C72 C 0.3560(14) 0.1016(7) -0.0545(13) 0.060(4) Uani 1 1 d . . . H72 H 0.3139 0.0728 -0.1129 0.073 Uiso 1 1 calc R . . C73 C 0.3451(14) 0.0986(6) 0.0477(13) 0.055(4) Uani 1 1 d . A . C74 C 0.2764(12) 0.0407(5) 0.0702(12) 0.090(6) Uani 1 1 d D . . F10 F 0.314(2) 0.0203(9) 0.1809(12) 0.218(19) Uani 0.50 1 d PD D 1 F11 F 0.283(3) -0.0074(7) 0.011(2) 0.184(14) Uani 0.50 1 d PD D 1 F12 F 0.1611(15) 0.0594(8) 0.029(2) 0.109(6) Uani 0.50 1 d PD D 1 F10' F 0.182(2) 0.0184(9) -0.0295(13) 0.218(19) Uani 0.50 1 d PD D 2 F11' F 0.227(2) 0.0586(8) 0.137(2) 0.184(14) Uani 0.50 1 d PD D 2 F12' F 0.3593(14) -0.0012(8) 0.121(2) 0.109(6) Uani 0.50 1 d PD D 2 C75 C 0.1989(19) 0.4154(10) 0.278(2) 0.105(6) Uiso 1 1 d . . . H75A H 0.2349 0.3805 0.3292 0.126 Uiso 1 1 calc R . . H75B H 0.1441 0.4358 0.3031 0.126 Uiso 1 1 calc R . . C76 C 0.128(2) 0.3952(12) 0.161(2) 0.138(9) Uiso 1 1 d . . . H76A H 0.0444 0.4108 0.1292 0.208 Uiso 1 1 calc R . . H76B H 0.1255 0.3516 0.1592 0.208 Uiso 1 1 calc R . . H76C H 0.1654 0.4096 0.1142 0.208 Uiso 1 1 calc R . . C77 C 0.4051(14) 0.4191(7) 0.2812(16) 0.075(5) Uiso 1 1 d . . . H77A H 0.4281 0.3868 0.3390 0.090 Uiso 1 1 calc R . . H77B H 0.3652 0.4006 0.2037 0.090 Uiso 1 1 calc R . . C78 C 0.5161(16) 0.4493(8) 0.2966(18) 0.087(5) Uiso 1 1 d . . . H78A H 0.5480 0.4741 0.3662 0.130 Uiso 1 1 calc R . . H78B H 0.4973 0.4745 0.2292 0.130 Uiso 1 1 calc R . . H78C H 0.5777 0.4196 0.3046 0.130 Uiso 1 1 calc R . . C79 C 0.2612(15) 0.5042(7) 0.1887(15) 0.072(4) Uiso 1 1 d . . . H79A H 0.3295 0.5288 0.1927 0.086 Uiso 1 1 calc R . . H79B H 0.2277 0.4808 0.1162 0.086 Uiso 1 1 calc R . . C80 C 0.1619(18) 0.5446(9) 0.188(2) 0.103(6) Uiso 1 1 d . . . H80A H 0.1787 0.5526 0.2672 0.154 Uiso 1 1 calc R . . H80B H 0.0823 0.5250 0.1458 0.154 Uiso 1 1 calc R . . H80C H 0.1610 0.5822 0.1493 0.154 Uiso 1 1 calc R . . C81 C 0.3619(19) 0.4856(9) 0.4106(19) 0.098(6) Uiso 1 1 d . . . H81A H 0.2968 0.5090 0.4157 0.118 Uiso 1 1 calc R . . H81B H 0.4261 0.5143 0.4183 0.118 Uiso 1 1 calc R . . C82 C 0.420(2) 0.4438(13) 0.520(3) 0.156(10) Uiso 1 1 d . . . H82A H 0.4180 0.4024 0.4953 0.234 Uiso 1 1 calc R . . H82B H 0.3732 0.4472 0.5628 0.234 Uiso 1 1 calc R . . H82C H 0.5050 0.4557 0.5700 0.234 Uiso 1 1 calc R . . N1 N 0.3094(13) 0.4613(5) 0.2937(12) 0.074(4) Uani 1 1 d . . . O1 O 0.3480(7) 0.2471(4) 0.2541(7) 0.044(3) Uani 1 1 d . . . O2 O 0.2502(7) 0.2358(9) 0.0095(7) 0.064(2) Uani 1 1 d . . . O3 O 0.4182(9) 0.3322(5) 0.0797(11) 0.063(3) Uani 1 1 d . . . O4 O 0.6408(9) 0.2779(5) 0.1332(10) 0.068(3) Uani 1 1 d . . . O5 O 0.6308(10) 0.1699(4) 0.2839(9) 0.057(3) Uani 1 1 d . . . O6 O 0.5948(9) 0.2878(4) 0.3413(10) 0.056(3) Uani 1 1 d . . . O7 O 0.4794(8) 0.1896(4) -0.0047(9) 0.055(2) Uani 1 1 d . . . O8 O 0.3887(11) 0.1327(4) 0.1332(10) 0.067(3) Uani 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 0.0528(3) 0.0491(3) 0.0417(3) -0.0033(6) 0.0224(2) 0.0019(6) C1 0.066(10) 0.067(9) 0.053(9) -0.002(7) -0.002(8) -0.009(7) C2 0.081(9) 0.084(11) 0.077(9) 0.032(9) 0.073(8) 0.032(9) C3 0.108(12) 0.147(15) 0.055(8) -0.031(17) 0.057(9) -0.05(2) C4 0.066(9) 0.095(11) 0.132(16) 0.02(2) 0.038(10) 0.009(16) C5 0.075(10) 0.094(14) 0.062(10) -0.008(8) 0.046(9) -0.002(8) C6 0.080(10) 0.074(9) 0.038(7) 0.010(7) 0.037(8) 0.012(8) C7 0.085(12) 0.068(11) 0.064(11) -0.010(8) 0.018(9) 0.001(9) C8 0.126(16) 0.20(2) 0.015(7) 0.013(9) 0.037(10) 0.027(16) C9 0.083(12) 0.145(17) 0.061(11) -0.019(11) 0.053(10) -0.001(12) C10 0.112(16) 0.15(2) 0.090(16) -0.014(13) 0.050(13) 0.004(13) C11 0.070(9) 0.072(8) 0.063(8) 0.042(11) 0.042(7) 0.062(11) C12 0.061(7) 0.082(15) 0.039(6) -0.001(9) 0.020(6) -0.033(10) C13 0.067(8) 0.032(10) 0.047(6) 0.002(6) 0.034(6) 0.001(7) C14 0.058(10) 0.16(3) 0.079(13) 0.026(17) 0.020(10) 0.011(13) F1 0.059(7) 0.181(17) 0.082(9) -0.057(10) 0.040(7) -0.053(9) F2 0.045(8) 0.170(17) 0.041(7) -0.028(9) -0.003(6) -0.025(8) F3 0.098(14) 0.165(19) 0.114(19) 0.007(12) 0.038(12) -0.037(13) F1' 0.059(7) 0.181(17) 0.082(9) -0.057(10) 0.040(7) -0.053(9) F2' 0.045(8) 0.170(17) 0.041(7) -0.028(9) -0.003(6) -0.025(8) F3' 0.098(14) 0.165(19) 0.114(19) 0.007(12) 0.038(12) -0.037(13) C31 0.059(9) 0.035(7) 0.068(10) 0.001(7) 0.025(9) 0.007(6) C21 0.073(7) 0.120(9) 0.118(10) 0.029(8) 0.048(7) 0.011(7) C22 0.069(6) 0.059(5) 0.053(5) -0.003(4) 0.036(5) 0.003(4) C23 0.092(8) 0.143(11) 0.096(9) 0.026(8) 0.045(7) 0.017(8) C24 0.149(12) 0.143(12) 0.127(12) -0.030(9) 0.107(10) -0.034(9) C25 0.105(8) 0.052(5) 0.104(8) 0.026(5) 0.057(7) 0.016(5) C26 0.099(9) 0.116(9) 0.114(10) -0.005(8) 0.067(8) 0.007(7) C27 0.172(13) 0.095(9) 0.140(13) -0.002(8) 0.104(11) -0.004(9) C28 0.167(13) 0.169(14) 0.112(11) 0.052(10) 0.072(10) 0.086(11) C29 0.236(19) 0.147(14) 0.25(2) 0.042(14) 0.206(18) 0.016(13) C30 0.161(15) 0.211(18) 0.151(15) 0.024(13) 0.130(13) 0.023(13) C32 0.078(11) 0.052(9) 0.090(12) 0.003(8) 0.052(10) -0.002(8) C33 0.036(8) 0.079(12) 0.064(10) -0.020(9) 0.010(7) -0.010(8) C34 0.064(11) 0.083(13) 0.106(16) 0.036(12) 0.004(11) -0.030(9) F4 0.133(19) 0.24(3) 0.19(3) 0.03(2) 0.12(2) 0.06(2) F5 0.083(12) 0.178(17) 0.099(13) 0.004(12) 0.070(11) 0.036(11) F6 0.14(2) 0.21(3) 0.28(4) -0.14(3) 0.14(3) -0.09(2) F4' 0.133(19) 0.24(3) 0.19(3) 0.03(2) 0.12(2) 0.06(2) F5' 0.083(12) 0.178(17) 0.099(13) 0.004(12) 0.070(11) 0.036(11) F6' 0.14(2) 0.21(3) 0.28(4) -0.14(3) 0.14(3) -0.09(2) C41 0.073(7) 0.120(9) 0.118(10) 0.029(8) 0.048(7) 0.011(7) C42 0.069(6) 0.059(5) 0.053(5) -0.003(4) 0.036(5) 0.003(4) C43 0.092(8) 0.143(11) 0.096(9) 0.026(8) 0.045(7) 0.017(8) C44 0.149(12) 0.143(12) 0.127(12) -0.030(9) 0.107(10) -0.034(9) C45 0.105(8) 0.052(5) 0.104(8) 0.026(5) 0.057(7) 0.016(5) C46 0.099(9) 0.116(9) 0.114(10) -0.005(8) 0.067(8) 0.007(7) C49 0.236(19) 0.147(14) 0.25(2) 0.042(14) 0.206(18) 0.016(13) C48 0.167(13) 0.169(14) 0.112(11) 0.052(10) 0.072(10) 0.086(11) C47 0.172(13) 0.095(9) 0.140(13) -0.002(8) 0.104(11) -0.004(9) C50 0.161(15) 0.211(18) 0.151(15) 0.024(13) 0.130(13) 0.023(13) C51 0.080(12) 0.032(8) 0.126(17) 0.015(9) 0.075(13) 0.003(8) C52 0.046(9) 0.13(3) 0.066(10) 0.038(12) 0.025(9) 0.057(13) C53 0.058(11) 0.141(17) 0.063(12) -0.043(12) 0.034(11) -0.024(13) C61 0.073(7) 0.120(9) 0.118(10) 0.029(8) 0.048(7) 0.011(7) C62 0.069(6) 0.059(5) 0.053(5) -0.003(4) 0.036(5) 0.003(4) C63 0.092(8) 0.143(11) 0.096(9) 0.026(8) 0.045(7) 0.017(8) C64 0.149(12) 0.143(12) 0.127(12) -0.030(9) 0.107(10) -0.034(9) C65 0.105(8) 0.052(5) 0.104(8) 0.026(5) 0.057(7) 0.016(5) C66 0.099(9) 0.116(9) 0.114(10) -0.005(8) 0.067(8) 0.007(7) C67 0.172(13) 0.095(9) 0.140(13) -0.002(8) 0.104(11) -0.004(9) C68 0.167(13) 0.169(14) 0.112(11) 0.052(10) 0.072(10) 0.086(11) C69 0.236(19) 0.147(14) 0.25(2) 0.042(14) 0.206(18) 0.016(13) C70 0.161(15) 0.211(18) 0.151(15) 0.024(13) 0.130(13) 0.023(13) C71 0.037(7) 0.063(9) 0.063(9) -0.020(8) 0.001(7) 0.000(7) C72 0.064(9) 0.061(9) 0.050(9) -0.020(7) 0.022(8) -0.002(8) C73 0.086(11) 0.037(7) 0.062(9) -0.010(7) 0.052(9) -0.003(7) C74 0.100(15) 0.092(13) 0.099(16) -0.046(12) 0.066(14) -0.028(11) F10 0.35(4) 0.034(9) 0.107(14) 0.004(9) -0.03(2) -0.068(14) F11 0.38(4) 0.072(12) 0.28(3) -0.096(15) 0.30(3) -0.135(18) F12 0.129(14) 0.062(9) 0.127(16) -0.020(9) 0.052(13) -0.017(9) F10' 0.35(4) 0.034(9) 0.107(14) 0.004(9) -0.03(2) -0.068(14) F11' 0.38(4) 0.072(12) 0.28(3) -0.096(15) 0.30(3) -0.135(18) F12' 0.129(14) 0.062(9) 0.127(16) -0.020(9) 0.052(13) -0.017(9) N1 0.102(10) 0.050(7) 0.069(9) -0.005(6) 0.038(8) 0.012(7) O1 0.051(5) 0.050(8) 0.040(4) -0.001(4) 0.028(4) 0.008(4) O2 0.051(4) 0.093(6) 0.044(4) -0.024(9) 0.019(4) -0.019(10) O3 0.055(6) 0.058(7) 0.079(8) -0.005(6) 0.035(6) 0.005(5) O4 0.070(7) 0.052(6) 0.088(8) 0.005(6) 0.042(6) -0.006(5) O5 0.061(6) 0.047(6) 0.053(6) -0.010(5) 0.018(6) 0.023(5) O6 0.056(6) 0.049(6) 0.065(7) -0.016(5) 0.032(6) -0.001(4) O7 0.056(6) 0.055(6) 0.063(6) -0.005(5) 0.035(5) -0.003(4) O8 0.088(8) 0.037(5) 0.064(7) -0.004(5) 0.024(6) -0.018(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 O5 2.324(9) . ? Eu1 O3 2.340(11) . ? Eu1 O1 2.354(8) . ? Eu1 O7 2.362(10) . ? Eu1 O8 2.408(10) . ? Eu1 O6 2.413(9) . ? Eu1 O4 2.424(10) . ? Eu1 O2 2.462(7) . ? C1 C2 1.3900 . ? C1 C6 1.3901 . ? C1 H1 0.9300 . ? C2 C3 1.3900 . ? C2 C11 1.459(12) . ? C3 C4 1.3900 . ? C3 H3 0.9300 . ? C4 C5 1.3900 . ? C4 H4 0.9300 . ? C5 C6 1.3900 . ? C5 C10 1.3900 . ? C6 C7 1.3900 . ? C7 C8 1.3900 . ? C7 H7 0.9300 . ? C8 C9 1.3900 . ? C8 H8 0.9300 . ? C9 C10 1.3900 . ? C9 H9 0.9300 . ? C10 H10 0.9300 . ? C11 O1 1.306(16) . ? C11 C12 1.412(18) . ? C12 C13 1.364(18) . ? C12 H12 0.9300 . ? C13 O2 1.221(15) . ? C13 C14 1.595(17) . ? C14 F3 1.303(9) . ? C14 F2 1.312(9) . ? C14 F3' 1.317(9) . ? C14 F2' 1.317(9) . ? C14 F1 1.328(9) . ? C14 F1' 1.348(9) . ? C31 O3 1.277(13) . ? C31 C32 1.386(17) . ? C31 C22 1.4612 . ? C21 C22 1.3900 . ? C21 C26 1.3900 . ? C21 H21 0.9300 . ? C22 C23 1.3900 . ? C23 C24 1.3900 . ? C23 H23 0.9300 . ? C24 C25 1.3900 . ? C24 H24 0.9300 . ? C25 C26 1.3900 . ? C25 C30 1.3900 . ? C26 C27 1.3900 . ? C27 C28 1.3900 . ? C27 H27 0.9300 . ? C28 C29 1.3900 . ? C28 H28 0.9300 . ? C29 C30 1.3900 . ? C29 H29 0.9300 . ? C30 H30 0.9300 . ? C32 C33 1.39(2) . ? C32 H32 0.9300 . ? C33 O4 1.194(19) . ? C33 C34 1.576(19) . ? C34 F6' 1.318(8) . ? C34 F5' 1.318(9) . ? C34 F4' 1.321(9) . ? C34 F4 1.322(9) . ? C34 F6 1.323(9) . ? C34 F5 1.342(9) . ? C41 C42 1.3900 . ? C41 C46 1.3900 . ? C41 H41 0.9300 . ? C42 C43 1.3900 . ? C42 C51 1.427(16) . ? C43 C44 1.3900 . ? C43 H43 0.9300 . ? C44 C45 1.3900 . ? C44 H44 0.9300 . ? C45 C46 1.3900 . ? C45 C50 1.3900 . ? C46 C49 1.3900 . ? C49 C48 1.3900 . ? C49 H49 0.9300 . ? C48 C47 1.3900 . ? C48 H48 0.9300 . ? C47 C50 1.3900 . ? C47 H47 0.9300 . ? C50 H50 0.9300 . ? C51 O5 1.24(2) . ? C51 C52 1.38(3) . ? C52 C53 1.32(3) . ? C52 H52 0.9300 . ? C53 O6 1.37(2) . ? C53 C54 1.63(2) . ? C54 F7 1.339(9) . ? C54 F8' 1.306(9) . ? C54 F9' 1.293(9) . ? C54 F9 1.325(9) . ? C54 F8 1.329(9) . ? C54 F7' 1.333(9) . ? C61 C62 1.3900 . ? C61 C66 1.3900 . ? C61 H61 0.9300 . ? C62 C63 1.3900 . ? C62 C71 1.523(18) . ? C63 C64 1.3900 . ? C63 H63 0.9300 . ? C64 C65 1.3900 . ? C64 H64 0.9300 . ? C65 C66 1.3900 . ? C65 C70 1.3900 . ? C66 C67 1.3900 . ? C67 C68 1.3900 . ? C67 H67 0.9300 . ? C68 C69 1.3900 . ? C68 H68 0.9300 . ? C69 C70 1.3900 . ? C69 H69 0.9300 . ? C70 H70 0.9300 . ? C71 O7 1.257(16) . ? C71 C72 1.42(2) . ? C72 C73 1.38(2) . ? C72 H72 0.9300 . ? C73 O8 1.226(17) . ? C73 C74 1.620(19) . ? C74 F12' 1.294(9) . ? C74 F12 1.307(9) . ? C74 F11' 1.312(8) . ? C74 F11 1.325(8) . ? C74 F10' 1.346(9) . ? C74 F10 1.350(9) . ? C75 C76 1.41(3) . ? C75 N1 1.61(2) . ? C75 H75A 0.9700 . ? C75 H75B 0.9700 . ? C76 H76A 0.9600 . ? C76 H76B 0.9600 . ? C76 H76C 0.9600 . ? C77 C78 1.43(2) . ? C77 N1 1.55(2) . ? C77 H77A 0.9700 . ? C77 H77B 0.9700 . ? C78 H78A 0.9600 . ? C78 H78B 0.9600 . ? C78 H78C 0.9600 . ? C79 C80 1.49(2) . ? C79 N1 1.52(2) . ? C79 H79A 0.9700 . ? C79 H79B 0.9700 . ? C80 H80A 0.9600 . ? C80 H80B 0.9600 . ? C80 H80C 0.9600 . ? C81 N1 1.43(2) . ? C81 C82 1.55(3) . ? C81 H81A 0.9700 . ? C81 H81B 0.9700 . ? C82 H82A 0.9600 . ? C82 H82B 0.9600 . ? C82 H82C 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 O5 Eu1 O3 146.3(4) . . ? O5 Eu1 O1 103.9(4) . . ? O3 Eu1 O1 90.1(3) . . ? O5 Eu1 O7 89.7(3) . . ? O3 Eu1 O7 96.6(4) . . ? O1 Eu1 O7 144.4(3) . . ? O5 Eu1 O8 71.8(4) . . ? O3 Eu1 O8 141.4(3) . . ? O1 Eu1 O8 81.7(4) . . ? O7 Eu1 O8 71.3(4) . . ? O5 Eu1 O6 72.1(3) . . ? O3 Eu1 O6 83.8(4) . . ? O1 Eu1 O6 72.1(3) . . ? O7 Eu1 O6 143.4(3) . . ? O8 Eu1 O6 127.9(4) . . ? O5 Eu1 O4 81.6(4) . . ? O3 Eu1 O4 69.9(3) . . ? O1 Eu1 O4 144.0(3) . . ? O7 Eu1 O4 69.8(3) . . ? O8 Eu1 O4 132.4(4) . . ? O6 Eu1 O4 76.2(4) . . ? O5 Eu1 O2 142.7(5) . . ? O3 Eu1 O2 70.7(5) . . ? O1 Eu1 O2 71.1(3) . . ? O7 Eu1 O2 78.2(3) . . ? O8 Eu1 O2 70.9(5) . . ? O6 Eu1 O2 134.6(4) . . ? O4 Eu1 O2 124.8(4) . . ? C2 C1 C6 120.0 . . ? C2 C1 H1 120.0 . . ? C6 C1 H1 120.0 . . ? C1 C2 C3 120.0 . . ? C1 C2 C11 124.7(6) . . ? C3 C2 C11 115.3(6) . . ? C4 C3 C2 120.0 . . ? C4 C3 H3 120.0 . . ? C2 C3 H3 120.0 . . ? C3 C4 C5 120.0 . . ? C3 C4 H4 120.0 . . ? C5 C4 H4 120.0 . . ? C6 C5 C4 120.0 . . ? C6 C5 C10 120.0 . . ? C4 C5 C10 120.0 . . ? C5 C6 C7 120.0 . . ? C5 C6 C1 120.0 . . ? C7 C6 C1 120.0 . . ? C8 C7 C6 120.0 . . ? C8 C7 H7 120.0 . . ? C6 C7 H7 120.0 . . ? C7 C8 C9 120.0 . . ? C7 C8 H8 120.0 . . ? C9 C8 H8 120.0 . . ? C10 C9 C8 120.0 . . ? C10 C9 H9 120.0 . . ? C8 C9 H9 120.0 . . ? C9 C10 C5 120.0 . . ? C9 C10 H10 120.0 . . ? C5 C10 H10 120.0 . . ? O1 C11 C12 119.0(11) . . ? O1 C11 C2 112.0(12) . . ? C12 C11 C2 127.9(11) . . ? C13 C12 C11 126.6(13) . . ? C13 C12 H12 116.7 . . ? C11 C12 H12 116.7 . . ? O2 C13 C12 129.1(12) . . ? O2 C13 C14 113.7(11) . . ? C12 C13 C14 116.6(11) . . ? F3 C14 F2 112.0(8) . . ? F3 C14 F3' 146.6(15) . . ? F2 C14 F3' 57.5(5) . . ? F3 C14 F2' 57.6(5) . . ? F2 C14 F2' 145.5(14) . . ? F3' C14 F2' 110.9(8) . . ? F3 C14 F1 109.0(9) . . ? F2 C14 F1 108.6(9) . . ? F3' C14 F1 55.9(5) . . ? F2' C14 F1 55.7(5) . . ? F3 C14 F1' 56.3(5) . . ? F2 C14 F1' 55.9(5) . . ? F3' C14 F1' 106.9(9) . . ? F2' C14 F1' 106.7(8) . . ? F1 C14 F1' 128.5(15) . . ? F3 C14 C13 101.5(17) . . ? F2 C14 C13 108.6(15) . . ? F3' C14 C13 111.9(13) . . ? F2' C14 C13 105.8(11) . . ? F1 C14 C13 116.9(14) . . ? F1' C14 C13 114.5(11) . . ? O3 C31 C32 120.5(9) . . ? O3 C31 C22 115.8(5) . . ? C32 C31 C22 123.6(7) . . ? C22 C21 C26 120.0 . . ? C22 C21 H21 120.0 . . ? C26 C21 H21 120.0 . . ? C23 C22 C21 120.0 . . ? C23 C22 C31 116.4 . . ? C21 C22 C31 123.5 . . ? C24 C23 C22 120.0 . . ? C24 C23 H23 120.0 . . ? C22 C23 H23 120.0 . . ? C23 C24 C25 120.0 . . ? C23 C24 H24 120.0 . . ? C25 C24 H24 120.0 . . ? C26 C25 C30 120.0 . . ? C26 C25 C24 120.0 . . ? C30 C25 C24 120.0 . . ? C25 C26 C27 120.0 . . ? C25 C26 C21 120.0 . . ? C27 C26 C21 120.0 . . ? C28 C27 C26 120.0 . . ? C28 C27 H27 120.0 . . ? C26 C27 H27 120.0 . . ? C27 C28 C29 120.0 . . ? C27 C28 H28 120.0 . . ? C29 C28 H28 120.0 . . ? C30 C29 C28 120.0 . . ? C30 C29 H29 120.0 . . ? C28 C29 H29 120.0 . . ? C29 C30 C25 120.0 . . ? C29 C30 H30 120.0 . . ? C25 C30 H30 120.0 . . ? C33 C32 C31 123.6(13) . . ? C33 C32 H32 118.2 . . ? C31 C32 H32 118.2 . . ? O4 C33 C32 129.0(15) . . ? O4 C33 C34 115.6(14) . . ? C32 C33 C34 115.1(15) . . ? F6' C34 F5' 109.7(8) . . ? F6' C34 F4' 110.4(8) . . ? F5' C34 F4' 108.9(9) . . ? F6' C34 F4 56.0(5) . . ? F5' C34 F4 56.5(5) . . ? F4' C34 F4 140.9(15) . . ? F6' C34 F6 143.0(13) . . ? F5' C34 F6 55.5(5) . . ? F4' C34 F6 56.9(5) . . ? F4 C34 F6 109.4(9) . . ? F6' C34 F5 56.6(5) . . ? F5' C34 F5 134.4(13) . . ? F4' C34 F5 54.8(5) . . ? F4 C34 F5 106.7(8) . . ? F6 C34 F5 106.8(9) . . ? F6' C34 C33 101.7(9) . . ? F5' C34 C33 111.5(13) . . ? F4' C34 C33 114.5(15) . . ? F4 C34 C33 104.5(15) . . ? F6 C34 C33 115.2(13) . . ? F5 C34 C33 113.8(14) . . ? C42 C41 C46 120.0 . . ? C42 C41 H41 120.0 . . ? C46 C41 H41 120.0 . . ? C41 C42 C43 120.0 . . ? C41 C42 C51 137.3(9) . . ? C43 C42 C51 102.7(9) . . ? C44 C43 C42 120.0 . . ? C44 C43 H43 120.0 . . ? C42 C43 H43 120.0 . . ? C43 C44 C45 120.0 . . ? C43 C44 H44 120.0 . . ? C45 C44 H44 120.0 . . ? C46 C45 C44 120.0 . . ? C46 C45 C50 120.0 . . ? C44 C45 C50 120.0 . . ? C45 C46 C49 120.0 . . ? C45 C46 C41 120.0 . . ? C49 C46 C41 120.0 . . ? C48 C49 C46 120.0 . . ? C48 C49 H49 120.0 . . ? C46 C49 H49 120.0 . . ? C47 C48 C49 120.0 . . ? C47 C48 H48 120.0 . . ? C49 C48 H48 120.0 . . ? C48 C47 C50 120.0 . . ? C48 C47 H47 120.0 . . ? C50 C47 H47 120.0 . . ? C47 C50 C45 120.0 . . ? C47 C50 H50 120.0 . . ? C45 C50 H50 120.0 . . ? O5 C51 C52 126.6(14) . . ? O5 C51 C42 114.9(15) . . ? C52 C51 C42 118.0(17) . . ? C53 C52 C51 122.2(16) . . ? C53 C52 H52 118.9 . . ? C51 C52 H52 118.9 . . ? C52 C53 O6 128.8(17) . . ? C52 C53 C54 117.4(18) . . ? O6 C53 C54 113.7(16) . . ? F7 C54 F8' 57.1(5) . . ? F7 C54 F9' 55.5(5) . . ? F8' C54 F9' 111.0(9) . . ? F7 C54 F9 108.0(9) . . ? F8' C54 F9 55.9(5) . . ? F9' C54 F9 141.1(16) . . ? F7 C54 F8 107.2(9) . . ? F8' C54 F8 141.4(15) . . ? F9' C54 F8 56.4(5) . . ? F9 C54 F8 108.5(9) . . ? F7 C54 F7' 137.2(18) . . ? F8' C54 F7' 109.2(9) . . ? F9' C54 F7' 109.4(9) . . ? F9 C54 F7' 55.9(5) . . ? F8 C54 F7' 55.7(5) . . ? F7 C54 C53 103.8(18) . . ? F8' C54 C53 110.1(13) . . ? F9' C54 C53 98.1(12) . . ? F9 C54 C53 120.7(17) . . ? F8 C54 C53 107.9(13) . . ? F7' C54 C53 118.6(18) . . ? C62 C61 C66 120.0 . . ? C62 C61 H61 120.0 . . ? C66 C61 H61 120.0 . . ? C61 C62 C63 120.0 . . ? C61 C62 C71 125.2(6) . . ? C63 C62 C71 114.7(6) . . ? C64 C63 C62 120.0 . . ? C64 C63 H63 120.0 . . ? C62 C63 H63 120.0 . . ? C63 C64 C65 120.0 . . ? C63 C64 H64 120.0 . . ? C65 C64 H64 120.0 . . ? C66 C65 C64 120.0 . . ? C66 C65 C70 120.0 . . ? C64 C65 C70 120.0 . . ? C67 C66 C65 120.0 . . ? C67 C66 C61 120.0 . . ? C65 C66 C61 120.0 . . ? C66 C67 C68 120.0 . . ? C66 C67 H67 120.0 . . ? C68 C67 H67 120.0 . . ? C69 C68 C67 120.0 . . ? C69 C68 H68 120.0 . . ? C67 C68 H68 120.0 . . ? C68 C69 C70 120.0 . . ? C68 C69 H69 120.0 . . ? C70 C69 H69 120.0 . . ? C69 C70 C65 120.0 . . ? C69 C70 H70 120.0 . . ? C65 C70 H70 120.0 . . ? O7 C71 C72 122.4(15) . . ? O7 C71 C62 116.6(13) . . ? C72 C71 C62 120.9(11) . . ? C73 C72 C71 123.3(13) . . ? C73 C72 H72 118.3 . . ? C71 C72 H72 118.3 . . ? O8 C73 C72 128.9(14) . . ? O8 C73 C74 111.3(13) . . ? C72 C73 C74 119.5(12) . . ? F12' C74 F12 149.2(13) . . ? F12' C74 F11' 111.5(7) . . ? F12 C74 F11' 56.2(5) . . ? F12' C74 F11 58.6(5) . . ? F12 C74 F11 111.0(7) . . ? F11' C74 F11 141.3(12) . . ? F12' C74 F10' 109.4(8) . . ? F12 C74 F10' 57.4(5) . . ? F11' C74 F10' 106.9(9) . . ? F11 C74 F10' 54.3(5) . . ? F12' C74 F10 55.4(5) . . ? F12 C74 F10 107.4(8) . . ? F11' C74 F10 56.2(5) . . ? F11 C74 F10 104.9(8) . . ? F10' C74 F10 126.7(14) . . ? F12' C74 C73 107.9(13) . . ? F12 C74 C73 102.9(13) . . ? F11' C74 C73 108.0(11) . . ? F11 C74 C73 110.6(11) . . ? F10' C74 C73 113.2(14) . . ? F10 C74 C73 120.1(13) . . ? C76 C75 N1 112(2) . . ? C76 C75 H75A 109.1 . . ? N1 C75 H75A 109.1 . . ? C76 C75 H75B 109.1 . . ? N1 C75 H75B 109.1 . . ? H75A C75 H75B 107.8 . . ? C75 C76 H76A 109.5 . . ? C75 C76 H76B 109.5 . . ? H76A C76 H76B 109.5 . . ? C75 C76 H76C 109.5 . . ? H76A C76 H76C 109.5 . . ? H76B C76 H76C 109.5 . . ? C78 C77 N1 114.2(14) . . ? C78 C77 H77A 108.7 . . ? N1 C77 H77A 108.7 . . ? C78 C77 H77B 108.7 . . ? N1 C77 H77B 108.7 . . ? H77A C77 H77B 107.6 . . ? C77 C78 H78A 109.5 . . ? C77 C78 H78B 109.5 . . ? H78A C78 H78B 109.5 . . ? C77 C78 H78C 109.5 . . ? H78A C78 H78C 109.5 . . ? H78B C78 H78C 109.5 . . ? C80 C79 N1 110.6(16) . . ? C80 C79 H79A 109.5 . . ? N1 C79 H79A 109.5 . . ? C80 C79 H79B 109.5 . . ? N1 C79 H79B 109.5 . . ? H79A C79 H79B 108.1 . . ? C79 C80 H80A 109.5 . . ? C79 C80 H80B 109.5 . . ? H80A C80 H80B 109.5 . . ? C79 C80 H80C 109.5 . . ? H80A C80 H80C 109.5 . . ? H80B C80 H80C 109.5 . . ? N1 C81 C82 121.3(18) . . ? N1 C81 H81A 107.0 . . ? C82 C81 H81A 107.0 . . ? N1 C81 H81B 107.0 . . ? C82 C81 H81B 107.0 . . ? H81A C81 H81B 106.7 . . ? C81 C82 H82A 109.5 . . ? C81 C82 H82B 109.5 . . ? H82A C82 H82B 109.5 . . ? C81 C82 H82C 109.5 . . ? H82A C82 H82C 109.5 . . ? H82B C82 H82C 109.5 . . ? C81 N1 C79 119.6(13) . . ? C81 N1 C77 110.2(14) . . ? C79 N1 C77 106.0(13) . . ? C81 N1 C75 107.3(15) . . ? C79 N1 C75 109.1(13) . . ? C77 N1 C75 103.4(12) . . ? C11 O1 Eu1 138.0(9) . . ? C13 O2 Eu1 130.2(9) . . ? C31 O3 Eu1 141.4(7) . . ? C33 O4 Eu1 134.4(10) . . ? C51 O5 Eu1 139.4(9) . . ? C53 O6 Eu1 129.7(10) . . ? C71 O7 Eu1 137.7(10) . . ? C73 O8 Eu1 131.9(11) . . ? 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 C6 C1 C2 C3 0.0 . . . . ? C6 C1 C2 C11 -178.4(9) . . . . ? C1 C2 C3 C4 0.0 . . . . ? C11 C2 C3 C4 178.5(8) . . . . ? C2 C3 C4 C5 0.0 . . . . ? C3 C4 C5 C6 0.0 . . . . ? C3 C4 C5 C10 180.0 . . . . ? C4 C5 C6 C7 180.0 . . . . ? C10 C5 C6 C7 0.0 . . . . ? C4 C5 C6 C1 0.0 . . . . ? C10 C5 C6 C1 180.0 . . . . ? C2 C1 C6 C5 0.0 . . . . ? C2 C1 C6 C7 180.0 . . . . ? C5 C6 C7 C8 0.0 . . . . ? C1 C6 C7 C8 180.0 . . . . ? C6 C7 C8 C9 0.0 . . . . ? C7 C8 C9 C10 0.0 . . . . ? C8 C9 C10 C5 0.0 . . . . ? C6 C5 C10 C9 0.0 . . . . ? C4 C5 C10 C9 180.0 . . . . ? C1 C2 C11 O1 -3.1(18) . . . . ? C3 C2 C11 O1 178.4(10) . . . . ? C1 C2 C11 C12 -171.0(16) . . . . ? C3 C2 C11 C12 10(2) . . . . ? O1 C11 C12 C13 2(3) . . . . ? C2 C11 C12 C13 169.2(17) . . . . ? C11 C12 C13 O2 -3(3) . . . . ? C11 C12 C13 C14 -173.1(19) . . . . ? O2 C13 C14 F3 120.4(17) . . . . ? C12 C13 C14 F3 -67.8(18) . . . . ? O2 C13 C14 F2 -121.4(17) . . . . ? C12 C13 C14 F2 50.5(19) . . . . ? O2 C13 C14 F3' -59.8(19) . . . . ? C12 C13 C14 F3' 112.1(17) . . . . ? O2 C13 C14 F2' 61.1(19) . . . . ? C12 C13 C14 F2' -127.0(16) . . . . ? O2 C13 C14 F1 2(2) . . . . ? C12 C13 C14 F1 173.8(16) . . . . ? O2 C13 C14 F1' 178.4(16) . . . . ? C12 C13 C14 F1' -10(2) . . . . ? C26 C21 C22 C23 0.0 . . . . ? C26 C21 C22 C31 177.9 . . . . ? O3 C31 C22 C23 145.4(7) . . . . ? C32 C31 C22 C23 -35.4(9) . . . . ? O3 C31 C22 C21 -32.6(7) . . . . ? C32 C31 C22 C21 146.6(9) . . . . ? C21 C22 C23 C24 0.0 . . . . ? C31 C22 C23 C24 -178.0 . . . . ? C22 C23 C24 C25 0.0 . . . . ? C23 C24 C25 C26 0.0 . . . . ? C23 C24 C25 C30 180.0 . . . . ? C30 C25 C26 C27 0.0 . . . . ? C24 C25 C26 C27 180.0 . . . . ? C30 C25 C26 C21 180.0 . . . . ? C24 C25 C26 C21 0.0 . . . . ? C22 C21 C26 C25 0.0 . . . . ? C22 C21 C26 C27 180.0 . . . . ? C25 C26 C27 C28 0.0 . . . . ? C21 C26 C27 C28 180.0 . . . . ? C26 C27 C28 C29 0.0 . . . . ? C27 C28 C29 C30 0.0 . . . . ? C28 C29 C30 C25 0.0 . . . . ? C26 C25 C30 C29 0.0 . . . . ? C24 C25 C30 C29 180.0 . . . . ? O3 C31 C32 C33 5(2) . . . . ? C22 C31 C32 C33 -173.8(11) . . . . ? C31 C32 C33 O4 -6(3) . . . . ? C31 C32 C33 C34 168.9(12) . . . . ? O4 C33 C34 F6' -97.1(14) . . . . ? C32 C33 C34 F6' 87.1(14) . . . . ? O4 C33 C34 F5' 19.7(17) . . . . ? C32 C33 C34 F5' -156.1(13) . . . . ? O4 C33 C34 F4' 143.9(13) . . . . ? C32 C33 C34 F4' -31.9(16) . . . . ? O4 C33 C34 F4 -39.5(16) . . . . ? C32 C33 C34 F4 144.7(14) . . . . ? O4 C33 C34 F6 80.6(16) . . . . ? C32 C33 C34 F6 -95.2(15) . . . . ? O4 C33 C34 F5 -155.5(13) . . . . ? C32 C33 C34 F5 28.7(17) . . . . ? C46 C41 C42 C43 0.0 . . . . ? C46 C41 C42 C51 177.9(11) . . . . ? C41 C42 C43 C44 0.0 . . . . ? C51 C42 C43 C44 -178.5(7) . . . . ? C42 C43 C44 C45 0.0 . . . . ? C43 C44 C45 C46 0.0 . . . . ? C43 C44 C45 C50 180.0 . . . . ? C44 C45 C46 C49 180.0 . . . . ? C50 C45 C46 C49 0.0 . . . . ? C44 C45 C46 C41 0.0 . . . . ? C50 C45 C46 C41 180.0 . . . . ? C42 C41 C46 C45 0.0 . . . . ? C42 C41 C46 C49 180.0 . . . . ? C45 C46 C49 C48 0.0 . . . . ? C41 C46 C49 C48 180.0 . . . . ? C46 C49 C48 C47 0.0 . . . . ? C49 C48 C47 C50 0.0 . . . . ? C48 C47 C50 C45 0.0 . . . . ? C46 C45 C50 C47 0.0 . . . . ? C44 C45 C50 C47 180.0 . . . . ? C41 C42 C51 O5 -5(2) . . . . ? C43 C42 C51 O5 173.2(12) . . . . ? C41 C42 C51 C52 168.5(10) . . . . ? C43 C42 C51 C52 -13.4(16) . . . . ? O5 C51 C52 C53 8(3) . . . . ? C42 C51 C52 C53 -164.9(15) . . . . ? C51 C52 C53 O6 -14(3) . . . . ? C51 C52 C53 C54 162.4(16) . . . . ? C52 C53 C54 F7 153.8(16) . . . . ? O6 C53 C54 F7 -29.1(17) . . . . ? C52 C53 C54 F8' -146.6(15) . . . . ? O6 C53 C54 F8' 30.5(19) . . . . ? C52 C53 C54 F9' 97.5(18) . . . . ? O6 C53 C54 F9' -85.4(16) . . . . ? C52 C53 C54 F9 -85.1(17) . . . . ? O6 C53 C54 F9 92.0(19) . . . . ? C52 C53 C54 F8 40(2) . . . . ? O6 C53 C54 F8 -142.6(14) . . . . ? C52 C53 C54 F7' -20(2) . . . . ? O6 C53 C54 F7' 157.2(14) . . . . ? C66 C61 C62 C63 0.0 . . . . ? C66 C61 C62 C71 176.0(7) . . . . ? C61 C62 C63 C64 0.0 . . . . ? C71 C62 C63 C64 -176.4(6) . . . . ? C62 C63 C64 C65 0.0 . . . . ? C63 C64 C65 C66 0.0 . . . . ? C63 C64 C65 C70 180.0 . . . . ? C64 C65 C66 C67 180.0 . . . . ? C70 C65 C66 C67 0.0 . . . . ? C64 C65 C66 C61 0.0 . . . . ? C70 C65 C66 C61 180.0 . . . . ? C62 C61 C66 C67 180.0 . . . . ? C62 C61 C66 C65 0.0 . . . . ? C65 C66 C67 C68 0.0 . . . . ? C61 C66 C67 C68 180.0 . . . . ? C66 C67 C68 C69 0.0 . . . . ? C67 C68 C69 C70 0.0 . . . . ? C68 C69 C70 C65 0.0 . . . . ? C66 C65 C70 C69 0.0 . . . . ? C64 C65 C70 C69 180.0 . . . . ? C61 C62 C71 O7 -151.4(8) . . . . ? C63 C62 C71 O7 24.8(13) . . . . ? C61 C62 C71 C72 32.7(15) . . . . ? C63 C62 C71 C72 -151.1(10) . . . . ? O7 C71 C72 C73 -6(2) . . . . ? C62 C71 C72 C73 169.8(12) . . . . ? C71 C72 C73 O8 3(3) . . . . ? C71 C72 C73 C74 -171.7(13) . . . . ? O8 C73 C74 F12' -87.8(17) . . . . ? C72 C73 C74 F12' 87.6(18) . . . . ? O8 C73 C74 F12 91.2(18) . . . . ? C72 C73 C74 F12 -93.5(18) . . . . ? O8 C73 C74 F11' 33(2) . . . . ? C72 C73 C74 F11' -151.8(17) . . . . ? O8 C73 C74 F11 -150.2(16) . . . . ? C72 C73 C74 F11 25.1(19) . . . . ? O8 C73 C74 F10' 151.0(16) . . . . ? C72 C73 C74 F10' -33.7(19) . . . . ? O8 C73 C74 F10 -28(2) . . . . ? C72 C73 C74 F10 147.4(17) . . . . ? C82 C81 N1 C79 -175.9(19) . . . . ? C82 C81 N1 C77 -53(3) . . . . ? C82 C81 N1 C75 59(2) . . . . ? C80 C79 N1 C81 -58(2) . . . . ? C80 C79 N1 C77 176.5(14) . . . . ? C80 C79 N1 C75 65.7(18) . . . . ? C78 C77 N1 C81 -63(2) . . . . ? C78 C77 N1 C79 67.7(18) . . . . ? C78 C77 N1 C75 -177.6(16) . . . . ? C76 C75 N1 C81 171.4(18) . . . . ? C76 C75 N1 C79 40(2) . . . . ? C76 C75 N1 C77 -72(2) . . . . ? C12 C11 O1 Eu1 -22(3) . . . . ? C2 C11 O1 Eu1 168.8(7) . . . . ? O5 Eu1 O1 C11 -115.6(15) . . . . ? O3 Eu1 O1 C11 95.4(15) . . . . ? O7 Eu1 O1 C11 -6.0(17) . . . . ? O8 Eu1 O1 C11 -46.7(15) . . . . ? O6 Eu1 O1 C11 178.8(15) . . . . ? O4 Eu1 O1 C11 149.6(14) . . . . ? O2 Eu1 O1 C11 25.8(15) . . . . ? C12 C13 O2 Eu1 19(3) . . . . ? C14 C13 O2 Eu1 -169.9(11) . . . . ? O5 Eu1 O2 C13 66(2) . . . . ? O3 Eu1 O2 C13 -119.5(19) . . . . ? O1 Eu1 O2 C13 -22.6(17) . . . . ? O7 Eu1 O2 C13 139.1(19) . . . . ? O8 Eu1 O2 C13 65.0(18) . . . . ? O6 Eu1 O2 C13 -60(2) . . . . ? O4 Eu1 O2 C13 -166.1(16) . . . . ? C32 C31 O3 Eu1 -10.9(19) . . . . ? C22 C31 O3 Eu1 168.3(9) . . . . ? O5 Eu1 O3 C31 44.0(17) . . . . ? O1 Eu1 O3 C31 159.7(13) . . . . ? O7 Eu1 O3 C31 -55.4(13) . . . . ? O8 Eu1 O3 C31 -123.6(12) . . . . ? O6 Eu1 O3 C31 87.7(13) . . . . ? O4 Eu1 O3 C31 10.2(13) . . . . ? O2 Eu1 O3 C31 -130.4(14) . . . . ? C32 C33 O4 Eu1 11(3) . . . . ? C34 C33 O4 Eu1 -164.4(8) . . . . ? O5 Eu1 O4 C33 -171.1(15) . . . . ? O3 Eu1 O4 C33 -9.2(15) . . . . ? O1 Eu1 O4 C33 -69.0(17) . . . . ? O7 Eu1 O4 C33 96.2(15) . . . . ? O8 Eu1 O4 C33 133.2(14) . . . . ? O6 Eu1 O4 C33 -97.6(15) . . . . ? O2 Eu1 O4 C33 37.7(17) . . . . ? C52 C51 O5 Eu1 0(3) . . . . ? C42 C51 O5 Eu1 172.6(9) . . . . ? O3 Eu1 O5 C51 45(2) . . . . ? O1 Eu1 O5 C51 -66.8(18) . . . . ? O7 Eu1 O5 C51 146.5(17) . . . . ? O8 Eu1 O5 C51 -143.1(18) . . . . ? O6 Eu1 O5 C51 -1.2(17) . . . . ? O4 Eu1 O5 C51 76.9(17) . . . . ? O2 Eu1 O5 C51 -143.7(15) . . . . ? C52 C53 O6 Eu1 13(3) . . . . ? C54 C53 O6 Eu1 -163.9(9) . . . . ? O5 Eu1 O6 C53 -4.3(14) . . . . ? O3 Eu1 O6 C53 -160.5(14) . . . . ? O1 Eu1 O6 C53 107.4(15) . . . . ? O7 Eu1 O6 C53 -67.9(16) . . . . ? O8 Eu1 O6 C53 43.8(15) . . . . ? O4 Eu1 O6 C53 -89.8(14) . . . . ? O2 Eu1 O6 C53 144.5(14) . . . . ? C72 C71 O7 Eu1 -12(2) . . . . ? C62 C71 O7 Eu1 171.9(7) . . . . ? O5 Eu1 O7 C71 90.8(13) . . . . ? O3 Eu1 O7 C71 -122.4(13) . . . . ? O1 Eu1 O7 C71 -23.0(16) . . . . ? O8 Eu1 O7 C71 19.9(13) . . . . ? O6 Eu1 O7 C71 149.2(12) . . . . ? O4 Eu1 O7 C71 171.9(14) . . . . ? O2 Eu1 O7 C71 -53.7(13) . . . . ? C72 C73 O8 Eu1 17(2) . . . . ? C74 C73 O8 Eu1 -168.1(9) . . . . ? O5 Eu1 O8 C73 -117.2(15) . . . . ? O3 Eu1 O8 C73 55.6(18) . . . . ? O1 Eu1 O8 C73 135.2(14) . . . . ? O7 Eu1 O8 C73 -21.2(14) . . . . ? O6 Eu1 O8 C73 -165.4(13) . . . . ? O4 Eu1 O8 C73 -57.8(15) . . . . ? O2 Eu1 O8 C73 62.4(14) . . . . ? _diffrn_measured_fraction_theta_max 0.779 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 0.902 _refine_diff_density_max 1.424 _refine_diff_density_min -0.957 _refine_diff_density_rms 0.141