Supplementary Material (ESI) for Dalton Transactions This journal is (c) The Royal Society of Chemistry 2006 data_global _journal_name_full 'Dalton Trans.' _journal_coden_Cambridge 0222 _publ_contact_author_name 'Anna Mondry' _publ_contact_author_address ; Faculty of Chemistry University of Wroclaw 14 F. Joliot-Curie Wroclaw 50-383 POLAND ; _publ_contact_author_email ANM@WCHUWR.CHEM.UNI.WROC.PL _publ_section_title ; From Structural Properties of the EuIII Complex with Ethylenediaminetetra-(methylenephosphonic acid)-H8EDTMP towards Biomedical Applications ; loop_ _publ_author_name 'Anna Mondry' 'Rafal Janicki' # Attachment 'EUEP(1).cif' data_euepabs _database_code_depnum_ccdc_archive 'CCDC 297437' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C14 H74 Eu N23 O25 P4' _chemical_formula_weight 1240.80 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' P P 0.1023 0.0942 '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 1 2(1)/n 1' 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 12.407(4) _cell_length_b 16.606(6) _cell_length_c 24.071(9) _cell_angle_alpha 90.00 _cell_angle_beta 101.85(3) _cell_angle_gamma 90.00 _cell_volume 4854(3) _cell_formula_units_Z 4 _cell_measurement_temperature 100(2) _cell_measurement_reflns_used no _cell_measurement_theta_min 3 _cell_measurement_theta_max 28.5 _exptl_crystal_description irreguler _exptl_crystal_colour colourless _exptl_crystal_size_max 0.4 _exptl_crystal_size_mid 0.25 _exptl_crystal_size_min 0.2 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.698 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 2568 _exptl_absorpt_coefficient_mu 1.525 _exptl_absorpt_correction_type 'analytical, from the shape' _exptl_absorpt_correction_T_min 0.773 _exptl_absorpt_correction_T_max 0.843 _exptl_absorpt_process_details ? _exptl_special_details ; no ; _diffrn_ambient_temperature 100(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 'Kuma KM4 with a CCD counter' _diffrn_measurement_method '\w scan' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 31261 _diffrn_reflns_av_R_equivalents 0.0415 _diffrn_reflns_av_sigmaI/netI 0.0719 _diffrn_reflns_limit_h_min -16 _diffrn_reflns_limit_h_max 16 _diffrn_reflns_limit_k_min -21 _diffrn_reflns_limit_k_max 17 _diffrn_reflns_limit_l_min -31 _diffrn_reflns_limit_l_max 31 _diffrn_reflns_theta_min 2.92 _diffrn_reflns_theta_max 28.48 _reflns_number_total 11207 _reflns_number_gt 7933 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'CrysAlis CCD ver. 1.171' _computing_cell_refinement 'CrysAlis RED ver. 1.171' _computing_data_reduction 'CrysAlis RED ver. 1.171' _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^)+(0.0300P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary vecmap _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 11207 _refine_ls_number_parameters 662 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0618 _refine_ls_R_factor_gt 0.0336 _refine_ls_wR_factor_ref 0.0660 _refine_ls_wR_factor_gt 0.0617 _refine_ls_goodness_of_fit_ref 0.935 _refine_ls_restrained_S_all 0.935 _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_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group Eu1 Eu 0.524784(13) 0.864920(9) 0.817458(6) 0.01077(4) Uani 1 d . . . P1 P 0.32189(7) 0.98853(5) 0.85950(3) 0.01153(17) Uani 1 d . . . P2 P 0.71527(7) 1.02367(5) 0.86060(3) 0.01532(19) Uani 1 d . . . P3 P 0.40904(7) 0.71847(5) 0.89521(3) 0.01210(17) Uani 1 d . . . P4 P 0.77390(7) 0.75312(5) 0.84613(3) 0.01198(17) Uani 1 d . . . O1 O 0.47405(18) 0.73894(12) 0.84961(9) 0.0176(5) Uani 1 d . . . O2 O 0.29853(17) 0.67889(13) 0.87239(10) 0.0223(6) Uani 1 d . . . O3 O 0.47787(17) 0.66765(12) 0.94262(8) 0.0133(5) Uani 1 d . . . O4 O 0.20712(17) 0.96431(12) 0.86706(9) 0.0149(5) Uani 1 d . . . O5 O 0.32900(16) 1.07993(12) 0.85339(8) 0.0135(5) Uani 1 d . . . O6 O 0.35858(17) 0.94245(12) 0.81121(8) 0.0143(5) Uani 1 d . . . O7 O 0.70379(17) 1.08290(12) 0.90777(9) 0.0157(5) Uani 1 d . . . O8 O 0.60237(18) 0.99406(12) 0.82818(9) 0.0195(5) Uani 1 d . . . O9 O 0.7858(2) 1.05652(13) 0.82098(9) 0.0253(6) Uani 1 d . . . O10 O 0.67673(17) 0.78676(12) 0.80260(8) 0.0144(5) Uani 1 d . . . O11 O 0.77355(17) 0.66160(12) 0.85213(9) 0.0157(5) Uani 1 d . . . O12 O 0.88404(17) 0.78266(12) 0.83561(9) 0.0163(5) Uani 1 d . . . C20 C 0.4394(2) 0.84480(17) 0.69864(13) 0.0121(7) Uani 1 d . . . O21 O 0.40027(17) 0.83654(12) 0.64584(8) 0.0155(5) Uani 1 d . . . O22 O 0.51555(17) 0.89830(12) 0.71764(8) 0.0141(5) Uani 1 d . . . O23 O 0.40640(17) 0.80211(12) 0.73670(9) 0.0159(5) Uani 1 d . . . C1 C 0.3777(2) 0.81748(17) 0.92161(13) 0.0132(7) Uani 1 d . . . H1A H 0.3088 0.8369 0.8990 0.016 Uiso 1 calc R . . H1B H 0.3686 0.8122 0.9605 0.016 Uiso 1 calc R . . C2 C 0.4233(2) 0.95957(17) 0.92337(13) 0.0126(7) Uani 1 d . . . H2A H 0.4842 0.9973 0.9290 0.015 Uiso 1 calc R . . H2B H 0.3893 0.9628 0.9562 0.015 Uiso 1 calc R . . C3 C 0.5607(2) 0.86037(18) 0.96694(12) 0.0111(6) Uani 1 d . . . H3A H 0.5729 0.8027 0.9700 0.013 Uiso 1 calc R . . H3B H 0.5426 0.8788 1.0022 0.013 Uiso 1 calc R . . C4 C 0.6655(2) 0.90131(18) 0.95896(12) 0.0120(7) Uani 1 d . . . H4A H 0.6539 0.9591 0.9571 0.014 Uiso 1 calc R . . H4B H 0.7237 0.8901 0.9916 0.014 Uiso 1 calc R . . C5 C 0.7817(2) 0.93270(17) 0.89263(13) 0.0130(7) Uani 1 d . . . H5A H 0.8221 0.9079 0.8667 0.016 Uiso 1 calc R . . H5B H 0.8340 0.9467 0.9270 0.016 Uiso 1 calc R . . C6 C 0.7520(2) 0.79325(17) 0.91383(12) 0.0115(6) Uani 1 d . . . H6A H 0.7048 0.7569 0.9295 0.014 Uiso 1 calc R . . H6B H 0.8221 0.7965 0.9405 0.014 Uiso 1 calc R . . N1 N 0.46609(19) 0.87705(14) 0.91925(10) 0.0097(5) Uani 1 d . . . N2 N 0.70087(19) 0.87409(14) 0.90657(10) 0.0102(5) Uani 1 d . . . C7 C 0.9589(3) 0.60938(19) 0.99585(14) 0.0191(8) Uani 1 d . . . N71 N 0.9590(2) 0.63923(15) 0.94496(10) 0.0176(6) Uani 1 d . . . H71A H 0.8981 0.6438 0.9205 0.021 Uiso 1 calc R . . H71B H 1.0199 0.6541 0.9363 0.021 Uiso 1 calc R . . N72 N 1.0525(2) 0.60140(18) 1.03382(12) 0.0291(7) Uani 1 d . . . H72A H 1.0518 0.5815 1.0667 0.035 Uiso 1 calc R . . H72B H 1.1137 0.6161 1.0255 0.035 Uiso 1 calc R . . N73 N 0.8661(2) 0.58629(19) 1.00980(13) 0.0340(8) Uani 1 d . . . H73A H 0.8048 0.5906 0.9857 0.041 Uiso 1 calc R . . H73B H 0.8669 0.5669 1.0430 0.041 Uiso 1 calc R . . C8 C 0.0954(3) 1.15289(18) 0.91870(13) 0.0135(7) Uani 1 d . . . N81 N 0.0930(2) 1.07699(15) 0.93460(11) 0.0170(6) Uani 1 d . . . H81A H 0.1406 1.0434 0.9269 0.020 Uiso 1 calc R . . H81B H 0.0439 1.0611 0.9527 0.020 Uiso 1 calc R . . N82 N 0.1705(2) 1.17835(15) 0.89084(11) 0.0162(6) Uani 1 d . . . H82A H 0.2185 1.1453 0.8829 0.019 Uiso 1 calc R . . H82B H 0.1713 1.2280 0.8807 0.019 Uiso 1 calc R . . N83 N 0.0244(2) 1.20587(16) 0.93244(11) 0.0189(6) Uani 1 d . . . H83A H -0.0232 1.1906 0.9517 0.023 Uiso 1 calc R . . H83B H 0.0261 1.2553 0.9220 0.023 Uiso 1 calc R . . C91 C 0.1160(3) 0.8030(2) 0.71296(14) 0.0223(8) Uani 1 d . . . N91 N 0.1466(2) 0.86768(17) 0.74544(11) 0.0279(7) Uani 1 d . . . H91A H 0.2153 0.8770 0.7585 0.033 Uiso 1 calc R . . H91B H 0.0975 0.8999 0.7533 0.033 Uiso 1 calc R . . N92 N 0.0098(2) 0.78973(17) 0.69310(11) 0.0248(7) Uani 1 d . . . H92A H -0.0109 0.7484 0.6721 0.030 Uiso 1 calc R . . H92B H -0.0385 0.8224 0.7012 0.030 Uiso 1 calc R . . N93 N 0.1910(2) 0.75348(16) 0.70088(11) 0.0222(7) Uani 1 d . . . H93A H 0.1712 0.7120 0.6799 0.027 Uiso 1 calc R . . H93B H 0.2597 0.7627 0.7140 0.027 Uiso 1 calc R . . C10 C 1.0428(3) 0.6294(2) 0.78350(14) 0.0201(7) Uani 1 d . . . N101 N 1.1198(3) 0.58148(17) 0.77138(13) 0.0334(8) Uani 1 d . . . H10A H 1.1022 0.5436 0.7468 0.040 Uiso 1 calc R . . H10B H 1.1874 0.5881 0.7881 0.040 Uiso 1 calc R . . N102 N 0.9413(3) 0.6185(2) 0.75792(14) 0.0460(10) Uani 1 d . . . H10C H 0.8903 0.6490 0.7658 0.055 Uiso 1 calc R . . H10D H 0.9248 0.5809 0.7331 0.055 Uiso 1 calc R . . N103 N 1.0701(2) 0.68666(15) 0.82167(11) 0.0193(6) Uani 1 d . . . H10E H 1.0202 0.7176 0.8300 0.023 Uiso 1 calc R . . H10F H 1.1379 0.6931 0.8382 0.023 Uiso 1 calc R . . C11 C 0.4593(3) 0.59150(19) 0.74431(14) 0.0201(8) Uani 1 d . . . N111 N 0.3591(2) 0.61312(16) 0.74897(11) 0.0209(7) Uani 1 d . . . H11A H 0.3502 0.6450 0.7758 0.025 Uiso 1 calc R . . H11B H 0.3028 0.5953 0.7252 0.025 Uiso 1 calc R . . N112 N 0.5445(2) 0.61946(17) 0.78119(12) 0.0298(8) Uani 1 d . . . H11C H 0.6101 0.6058 0.7787 0.036 Uiso 1 calc R . . H11D H 0.5344 0.6514 0.8078 0.036 Uiso 1 calc R . . N113 N 0.4728(3) 0.54248(19) 0.70321(13) 0.0409(9) Uani 1 d . . . H11E H 0.5380 0.5283 0.7002 0.049 Uiso 1 calc R . . H11F H 0.4165 0.5247 0.6794 0.049 Uiso 1 calc R . . C12 C 1.2057(3) 0.72726(19) 1.15313(14) 0.0158(7) Uani 1 d . . . N121 N 1.1799(2) 0.77754(15) 1.19069(11) 0.0200(6) Uani 1 d . . . H12A H 1.1566 0.7593 1.2195 0.024 Uiso 1 calc R . . H12B H 1.1863 0.8286 1.1864 0.024 Uiso 1 calc R . . N122 N 1.2417(2) 0.75558(15) 1.10834(11) 0.0188(6) Uani 1 d . . . H12C H 1.2480 0.8066 1.1040 0.023 Uiso 1 calc R . . H12D H 1.2585 0.7228 1.0838 0.023 Uiso 1 calc R . . N123 N 1.1961(2) 0.64849(15) 1.15941(12) 0.0196(6) Uani 1 d . . . H12E H 1.1729 0.6298 1.1882 0.024 Uiso 1 calc R . . H12F H 1.2131 0.6160 1.1347 0.024 Uiso 1 calc R . . C13 C 0.6716(3) 0.5314(2) 1.09064(14) 0.0183(7) Uani 1 d . . . N131 N 0.7544(2) 0.48038(16) 1.10604(12) 0.0249(7) Uani 1 d . . . H13A H 0.8199 0.4983 1.1188 0.030 Uiso 1 calc R . . H13B H 0.7428 0.4293 1.1033 0.030 Uiso 1 calc R . . N132 N 0.6878(2) 0.61009(15) 1.09460(12) 0.0217(7) Uani 1 d . . . H13C H 0.7529 0.6288 1.1073 0.026 Uiso 1 calc R . . H13D H 0.6334 0.6426 1.0845 0.026 Uiso 1 calc R . . N133 N 0.5709(2) 0.50294(16) 1.07007(13) 0.0276(7) Uani 1 d . . . H13E H 0.5169 0.5357 1.0595 0.033 Uiso 1 calc R . . H13F H 0.5599 0.4518 1.0674 0.033 Uiso 1 calc R . . OW1 O 0.47140(19) 0.67918(15) 1.05236(11) 0.0184(5) Uani 1 d . . . OW2 O 0.6652(2) 0.58838(14) 0.92696(11) 0.0200(6) Uani 1 d . . . OW3 O 0.49871(18) 0.99263(13) 0.62617(9) 0.0236(5) Uani 1 d . . . OW4 O 0.7950(2) 0.92024(18) 0.56938(12) 0.0275(6) Uani 1 d . . . OW5 O 0.1777(2) 0.71057(18) 0.96382(12) 0.0249(6) Uani 1 d . . . OW6 O 0.9019(2) 1.09005(15) 0.98643(12) 0.0220(6) Uani 1 d . . . OW7 O 0.7522(2) 1.01799(16) 0.71047(11) 0.0405(7) Uani 1 d . . . OW8 O 0.5136(2) 1.16851(15) 0.89611(11) 0.0181(6) Uani 1 d . . . OW9 O 0.0822(2) 0.84921(15) 0.90368(10) 0.0200(6) Uani 1 d . . . OW10 O 0.9037(2) 0.89278(18) 0.75595(12) 0.0283(6) Uiso 1 d . . . HW11 H 0.477(3) 0.729(3) 1.0638(18) 0.056(14) Uiso 1 d . . . HW12 H 0.469(3) 0.679(3) 1.015(2) 0.060(15) Uiso 1 d . . . HW21 H 0.686(3) 0.611(2) 0.9020(16) 0.030(13) Uiso 1 d . . . HW22 H 0.600(4) 0.618(3) 0.931(2) 0.081(17) Uiso 1 d . . . HW41 H 0.809(4) 0.965(3) 0.576(2) 0.070(18) Uiso 1 d . . . HW42 H 0.848(4) 0.891(3) 0.5641(18) 0.056(15) Uiso 1 d . . . HW51 H 0.150(3) 0.747(2) 0.9519(16) 0.026(13) Uiso 1 d . . . HW52 H 0.213(3) 0.694(2) 0.9442(17) 0.036(14) Uiso 1 d . . . HW61 H 0.839(3) 1.090(2) 0.9658(15) 0.021(11) Uiso 1 d . . . HW62 H 0.899(4) 1.102(3) 1.018(2) 0.068(18) Uiso 1 d . . . HW81 H 0.561(3) 1.141(2) 0.8973(16) 0.026(12) Uiso 1 d . . . HW82 H 0.464(4) 1.138(3) 0.8859(19) 0.061(17) Uiso 1 d . . . HW91 H 0.124(4) 0.887(3) 0.883(2) 0.100 Uiso 1 d . . . HW92 H 0.030(3) 0.842(2) 0.8880(15) 0.020(12) Uiso 1 d . . . HW01 H 0.885(3) 0.857(2) 0.7774(18) 0.059(14) Uiso 1 d . . . HW02 H 0.847(3) 0.916(2) 0.7518(15) 0.037(12) Uiso 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 0.01273(8) 0.00993(8) 0.00867(7) -0.00051(7) -0.00008(6) 0.00110(7) P1 0.0115(4) 0.0117(4) 0.0108(4) 0.0002(3) 0.0010(3) 0.0024(3) P2 0.0214(5) 0.0101(4) 0.0135(4) 0.0007(3) 0.0014(4) -0.0023(4) P3 0.0128(4) 0.0096(4) 0.0126(4) 0.0003(3) -0.0004(3) 0.0002(3) P4 0.0130(4) 0.0107(4) 0.0113(4) -0.0012(3) 0.0003(3) 0.0010(3) O1 0.0285(14) 0.0120(12) 0.0132(11) 0.0011(9) 0.0063(10) 0.0017(10) O2 0.0132(12) 0.0119(12) 0.0360(15) -0.0005(10) -0.0086(11) -0.0017(9) O3 0.0162(12) 0.0118(11) 0.0120(11) 0.0018(9) 0.0034(9) 0.0013(9) O4 0.0158(12) 0.0116(11) 0.0171(12) 0.0007(9) 0.0032(10) -0.0007(9) O5 0.0156(12) 0.0100(11) 0.0147(11) 0.0036(9) 0.0027(9) 0.0010(9) O6 0.0153(12) 0.0170(12) 0.0095(11) -0.0011(9) 0.0002(9) 0.0048(9) O7 0.0181(12) 0.0118(12) 0.0168(12) -0.0008(9) 0.0024(10) -0.0007(9) O8 0.0279(14) 0.0089(11) 0.0178(12) 0.0033(9) -0.0043(10) -0.0012(10) O9 0.0412(16) 0.0162(13) 0.0204(13) 0.0033(10) 0.0106(12) -0.0073(11) O10 0.0155(12) 0.0167(12) 0.0095(11) -0.0026(9) -0.0009(9) 0.0037(9) O11 0.0152(12) 0.0126(11) 0.0175(12) -0.0056(9) -0.0010(10) 0.0013(9) O12 0.0156(12) 0.0170(12) 0.0159(12) 0.0003(9) 0.0026(10) 0.0013(9) C20 0.0098(16) 0.0120(17) 0.0130(16) -0.0007(12) -0.0013(13) 0.0037(12) O21 0.0181(12) 0.0177(12) 0.0092(11) -0.0006(9) -0.0006(10) -0.0025(9) O22 0.0138(12) 0.0152(11) 0.0121(11) -0.0017(9) -0.0002(9) -0.0033(9) O23 0.0190(12) 0.0148(12) 0.0132(11) 0.0012(9) 0.0015(10) -0.0038(10) C1 0.0104(16) 0.0137(17) 0.0147(16) 0.0032(13) 0.0008(14) 0.0002(13) C2 0.0140(17) 0.0107(16) 0.0134(16) -0.0014(13) 0.0031(13) 0.0010(13) C3 0.0129(15) 0.0113(15) 0.0081(14) -0.0031(13) -0.0003(12) 0.0002(13) C4 0.0147(17) 0.0120(16) 0.0087(15) -0.0019(12) 0.0009(13) 0.0004(13) C5 0.0158(17) 0.0102(16) 0.0139(16) -0.0030(13) 0.0054(14) -0.0043(13) C6 0.0104(16) 0.0104(16) 0.0119(16) 0.0006(13) -0.0016(13) 0.0003(12) N1 0.0102(13) 0.0076(14) 0.0099(12) 0.0000(10) -0.0009(10) 0.0000(10) N2 0.0104(13) 0.0088(13) 0.0110(12) -0.0004(11) 0.0014(10) -0.0001(11) C7 0.0168(18) 0.0188(18) 0.0216(19) 0.0013(14) 0.0037(15) 0.0024(14) N71 0.0136(14) 0.0228(15) 0.0161(14) 0.0040(13) 0.0019(11) -0.0001(13) N72 0.0173(16) 0.046(2) 0.0208(16) 0.0094(15) -0.0020(13) 0.0006(14) N73 0.0179(17) 0.060(2) 0.0238(17) 0.0176(16) 0.0038(14) -0.0018(16) C8 0.0117(16) 0.0183(19) 0.0088(15) -0.0017(13) -0.0020(13) 0.0001(13) N81 0.0136(15) 0.0200(15) 0.0185(15) 0.0049(12) 0.0056(12) 0.0030(12) N82 0.0179(15) 0.0131(14) 0.0194(15) 0.0028(12) 0.0084(12) 0.0044(11) N83 0.0212(16) 0.0155(15) 0.0218(15) -0.0009(12) 0.0086(13) 0.0020(12) C91 0.027(2) 0.025(2) 0.0121(17) 0.0032(15) -0.0031(15) -0.0113(16) N91 0.0293(17) 0.0240(16) 0.0274(16) -0.0080(15) -0.0010(14) -0.0041(15) N92 0.0251(17) 0.0264(17) 0.0204(16) -0.0065(13) -0.0012(13) -0.0006(13) N93 0.0250(17) 0.0178(16) 0.0224(16) -0.0058(13) 0.0016(13) -0.0082(13) C10 0.0224(18) 0.0192(18) 0.0180(17) -0.0008(16) 0.0023(15) -0.0030(16) N101 0.054(2) 0.0196(17) 0.0338(19) -0.0057(14) 0.0252(17) 0.0004(16) N102 0.036(2) 0.048(2) 0.043(2) -0.0189(17) -0.0162(17) -0.0019(17) N103 0.0190(15) 0.0200(16) 0.0157(15) -0.0065(12) -0.0041(12) 0.0053(12) C11 0.022(2) 0.0120(18) 0.0230(19) -0.0040(15) -0.0038(16) 0.0019(14) N111 0.0159(15) 0.0290(17) 0.0178(15) -0.0102(12) 0.0033(12) -0.0032(12) N112 0.0194(16) 0.036(2) 0.0287(17) -0.0222(14) -0.0082(13) 0.0097(14) N113 0.0221(18) 0.048(2) 0.044(2) -0.0329(17) -0.0130(16) 0.0177(16) C12 0.0099(17) 0.0170(18) 0.0191(17) 0.0039(14) -0.0007(14) -0.0006(13) N121 0.0323(18) 0.0136(15) 0.0153(14) 0.0039(12) 0.0072(13) -0.0027(13) N122 0.0218(16) 0.0101(14) 0.0277(16) 0.0014(12) 0.0128(13) 0.0012(12) N123 0.0235(16) 0.0128(15) 0.0232(15) 0.0049(12) 0.0064(13) -0.0024(12) C13 0.0146(18) 0.0180(18) 0.0222(18) -0.0006(15) 0.0035(15) -0.0002(14) N131 0.0175(16) 0.0157(15) 0.0382(19) 0.0003(14) -0.0019(14) -0.0025(12) N132 0.0175(16) 0.0143(15) 0.0314(17) 0.0001(12) 0.0008(13) -0.0026(11) N133 0.0142(16) 0.0128(15) 0.052(2) 0.0011(14) -0.0010(14) 0.0009(12) OW1 0.0254(14) 0.0152(14) 0.0148(13) -0.0007(11) 0.0048(11) -0.0023(11) OW2 0.0140(13) 0.0181(14) 0.0284(15) 0.0060(12) 0.0060(11) 0.0011(10) OW3 0.0252(14) 0.0234(13) 0.0224(13) 0.0041(11) 0.0056(11) 0.0060(11) OW4 0.0222(15) 0.0158(15) 0.0482(18) -0.0055(13) 0.0156(13) -0.0019(12) OW5 0.0226(16) 0.0229(16) 0.0301(16) 0.0022(13) 0.0076(13) 0.0017(13) OW6 0.0183(15) 0.0297(15) 0.0180(14) -0.0048(12) 0.0036(12) -0.0013(12) OW7 0.0412(18) 0.0374(17) 0.0433(17) -0.0038(14) 0.0097(14) 0.0004(13) OW8 0.0174(14) 0.0126(13) 0.0243(14) -0.0020(11) 0.0041(12) 0.0006(12) OW9 0.0168(14) 0.0221(15) 0.0194(13) -0.0001(10) 0.0000(12) -0.0046(11) _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 O8 2.343(2) . yes Eu1 O1 2.361(2) . yes Eu1 O10 2.376(2) . yes Eu1 O6 2.409(2) . yes Eu1 O23 2.419(2) . yes Eu1 O22 2.446(2) . yes Eu1 N1 2.703(3) . yes Eu1 N2 2.734(3) . yes Eu1 C20 2.858(3) . no Eu1 P3 3.5473(12) . no Eu1 P4 3.5498(13) . no Eu1 P2 3.5505(13) . no P1 O4 1.526(2) . yes P1 O5 1.529(2) . yes P1 O6 1.537(2) . yes P1 C2 1.839(3) . yes P2 O9 1.521(2) . yes P2 O7 1.531(2) . yes P2 O8 1.538(2) . yes P2 C5 1.815(3) . yes P3 O2 1.518(2) . yes P3 O1 1.528(2) . yes P3 O3 1.531(2) . yes P3 C1 1.833(3) . yes P4 O12 1.521(2) . yes P4 O11 1.527(2) . yes P4 O10 1.531(2) . yes P4 C6 1.832(3) . yes C20 O21 1.271(3) . yes C20 O23 1.290(3) . yes C20 O22 1.309(3) . yes C1 N1 1.487(4) . no C2 N1 1.480(3) . no C3 N1 1.490(4) . no C3 C4 1.514(4) . yes C4 N2 1.488(4) . no C5 N2 1.484(4) . no C6 N2 1.480(4) . no C7 N73 1.321(4) . no C7 N71 1.321(4) . no C7 N72 1.328(4) . no C8 N81 1.319(4) . no C8 N82 1.324(4) . no C8 N83 1.334(4) . no C91 N93 1.319(4) . no C91 N92 1.325(4) . no C91 N91 1.336(4) . no C10 N102 1.297(4) . no C10 N103 1.317(4) . no C10 N101 1.321(4) . no C11 N112 1.318(4) . no C11 N113 1.318(4) . no C11 N111 1.320(4) . no C12 N121 1.318(4) . no C12 N123 1.325(4) . no C12 N122 1.334(4) . no C13 N132 1.322(4) . no C13 N131 1.326(4) . no C13 N133 1.332(4) . no 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 O8 Eu1 O1 154.99(7) . . yes O8 Eu1 O10 101.29(8) . . yes O1 Eu1 O10 80.70(7) . . yes O8 Eu1 O6 81.07(8) . . yes O1 Eu1 O6 102.22(8) . . yes O10 Eu1 O6 167.97(7) . . yes O8 Eu1 O23 130.62(7) . . yes O1 Eu1 O23 73.89(7) . . yes O10 Eu1 O23 90.76(7) . . yes O6 Eu1 O23 79.02(7) . . yes O8 Eu1 O22 80.56(7) . . yes O1 Eu1 O22 124.14(7) . . yes O10 Eu1 O22 81.63(7) . . yes O6 Eu1 O22 87.18(7) . . yes O23 Eu1 O22 53.84(7) . . yes O8 Eu1 N1 90.75(7) . . yes O1 Eu1 N1 68.24(7) . . yes O10 Eu1 N1 123.16(7) . . yes O6 Eu1 N1 68.30(7) . . yes O23 Eu1 N1 121.90(7) . . yes O22 Eu1 N1 155.05(7) . . yes O8 Eu1 N2 67.58(7) . . yes O1 Eu1 N2 90.92(7) . . yes O10 Eu1 N2 67.51(7) . . yes O6 Eu1 N2 123.71(7) . . yes O23 Eu1 N2 155.53(7) . . yes O22 Eu1 N2 128.83(7) . . yes N1 Eu1 N2 66.75(7) . . yes O8 Eu1 C20 106.06(8) . . no O1 Eu1 C20 98.94(8) . . no O10 Eu1 C20 85.88(8) . . no O6 Eu1 C20 82.15(8) . . no O23 Eu1 C20 26.66(7) . . no O22 Eu1 C20 27.18(7) . . no N1 Eu1 C20 143.34(8) . . no N2 Eu1 C20 149.77(8) . . no O8 Eu1 P3 140.45(6) . . no O1 Eu1 P3 19.14(5) . . no O10 Eu1 P3 97.16(6) . . no O6 Eu1 P3 88.01(6) . . no O23 Eu1 P3 83.31(6) . . no O22 Eu1 P3 137.00(5) . . no N1 Eu1 P3 50.16(5) . . no N2 Eu1 P3 88.23(6) . . no C20 Eu1 P3 109.92(7) . . no O8 Eu1 P4 97.80(6) . . no O1 Eu1 P4 75.69(6) . . no O10 Eu1 P4 19.49(5) . . no O6 Eu1 P4 172.53(5) . . no O23 Eu1 P4 106.95(6) . . no O22 Eu1 P4 99.95(6) . . no N1 Eu1 P4 104.40(6) . . no N2 Eu1 P4 49.67(5) . . no C20 Eu1 P4 105.22(7) . . no P3 Eu1 P4 88.25(3) . . no O8 Eu1 P2 19.00(5) . . no O1 Eu1 P2 140.21(6) . . no O10 Eu1 P2 87.05(6) . . no O6 Eu1 P2 97.54(6) . . no O23 Eu1 P2 144.40(5) . . no O22 Eu1 P2 90.75(5) . . no N1 Eu1 P2 88.08(6) . . no N2 Eu1 P2 49.64(5) . . no C20 Eu1 P2 117.85(7) . . no P3 Eu1 P2 132.22(3) . . no P4 Eu1 P2 80.25(3) . . no O4 P1 O5 110.29(12) . . no O4 P1 O6 112.81(12) . . no O5 P1 O6 112.93(12) . . no O4 P1 C2 109.05(13) . . no O5 P1 C2 107.26(13) . . no O6 P1 C2 104.12(13) . . no O4 P1 Eu1 127.94(9) . . no O5 P1 Eu1 119.20(9) . . no O6 P1 Eu1 32.80(8) . . no C2 P1 Eu1 71.57(10) . . no O9 P2 O7 112.80(13) . . no O9 P2 O8 112.18(13) . . no O7 P2 O8 111.60(13) . . no O9 P2 C5 107.19(14) . . no O7 P2 C5 108.85(13) . . no O8 P2 C5 103.67(13) . . no O9 P2 Eu1 121.11(10) . . no O7 P2 Eu1 122.43(9) . . no O8 P2 Eu1 29.75(8) . . no C5 P2 Eu1 73.93(10) . . no O2 P3 O1 114.04(13) . . no O2 P3 O3 110.81(13) . . no O1 P3 O3 111.24(12) . . no O2 P3 C1 105.88(13) . . no O1 P3 C1 103.32(13) . . no O3 P3 C1 111.19(13) . . no O2 P3 Eu1 122.64(10) . . no O1 P3 Eu1 30.44(8) . . no O3 P3 Eu1 123.16(9) . . no C1 P3 Eu1 72.88(10) . . no O12 P4 O11 110.90(12) . . no O12 P4 O10 112.12(12) . . no O11 P4 O10 114.26(12) . . no O12 P4 C6 109.46(13) . . no O11 P4 C6 105.91(13) . . no O10 P4 C6 103.67(13) . . no O12 P4 Eu1 125.11(9) . . no O11 P4 Eu1 121.32(9) . . no O10 P4 Eu1 31.16(8) . . no C6 P4 Eu1 72.57(10) . . no P3 O1 Eu1 130.42(12) . . no P1 O6 Eu1 126.99(11) . . no P2 O8 Eu1 131.25(12) . . no P4 O10 Eu1 129.35(11) . . no O21 C20 O23 122.6(3) . . no O21 C20 O22 121.5(3) . . no O23 C20 O22 115.9(3) . . no O21 C20 Eu1 179.2(2) . . no O23 C20 Eu1 57.31(15) . . no O22 C20 Eu1 58.56(14) . . no C20 O22 Eu1 94.26(17) . . no C20 O23 Eu1 96.03(17) . . no N1 C1 P3 111.9(2) . . no N1 C2 P1 112.3(2) . . no N1 C3 C4 112.3(2) . . no N2 C4 C3 112.4(2) . . no N2 C5 P2 111.9(2) . . no N2 C6 P4 111.30(19) . . no C2 N1 C1 109.6(2) . . no C2 N1 C3 110.9(2) . . no C1 N1 C3 108.5(2) . . no C2 N1 Eu1 107.26(16) . . no C1 N1 Eu1 108.86(17) . . no C3 N1 Eu1 111.61(17) . . no C6 N2 C5 109.2(2) . . no C6 N2 C4 111.7(2) . . no C5 N2 C4 108.8(2) . . no C6 N2 Eu1 107.24(16) . . no C5 N2 Eu1 109.10(17) . . no C4 N2 Eu1 110.76(17) . . no N73 C7 N71 120.7(3) . . no N73 C7 N72 118.7(3) . . no N71 C7 N72 120.6(3) . . no N81 C8 N82 120.8(3) . . no N81 C8 N83 120.2(3) . . no N82 C8 N83 119.0(3) . . no N93 C91 N92 120.7(3) . . no N93 C91 N91 120.1(3) . . no N92 C91 N91 119.1(3) . . no N102 C10 N103 121.2(3) . . no N102 C10 N101 119.1(3) . . no N103 C10 N101 119.7(3) . . no N112 C11 N113 121.0(3) . . no N112 C11 N111 119.1(3) . . no N113 C11 N111 119.9(3) . . no N121 C12 N123 120.5(3) . . no N121 C12 N122 120.0(3) . . no N123 C12 N122 119.5(3) . . no N132 C13 N131 120.9(3) . . no N132 C13 N133 119.7(3) . . no N131 C13 N133 119.4(3) . . no _diffrn_measured_fraction_theta_max 0.912 _diffrn_reflns_theta_full 28.48 _diffrn_measured_fraction_theta_full 0.912 _refine_diff_density_max 1.021 _refine_diff_density_min -0.590 _refine_diff_density_rms 0.105 # Attachment 'RAJ2(1).CIF' data_raj2 _database_code_depnum_ccdc_archive 'CCDC 297438' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C11 H24 Eu N5 O11' _chemical_formula_weight 554.31 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 'P 1 2(1)/c 1' 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 11.269(5) _cell_length_b 8.646(4) _cell_length_c 18.718(9) _cell_angle_alpha 90.00 _cell_angle_beta 90.07(4) _cell_angle_gamma 90.00 _cell_volume 1823.7(15) _cell_formula_units_Z 4 _cell_measurement_temperature 100(2) _cell_measurement_reflns_used 13521 _cell_measurement_theta_min 3.0 _cell_measurement_theta_max 28.5 _exptl_crystal_description irregular _exptl_crystal_colour colourless _exptl_crystal_size_max 0.4 _exptl_crystal_size_mid 0.17 _exptl_crystal_size_min 0.10 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 2.019 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1104 _exptl_absorpt_coefficient_mu 3.509 _exptl_absorpt_correction_type 'analytical, from the crystal shape' _exptl_absorpt_correction_T_min 0.325 _exptl_absorpt_correction_T_max 0.713 _exptl_special_details ; ? ; _diffrn_ambient_temperature 100(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 'Kuma KM4 with a CCD counter' _diffrn_measurement_method '\w scan' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 11182 _diffrn_reflns_av_R_equivalents 0.0369 _diffrn_reflns_av_sigmaI/netI 0.0249 _diffrn_reflns_limit_h_min -14 _diffrn_reflns_limit_h_max 14 _diffrn_reflns_limit_k_min -11 _diffrn_reflns_limit_k_max 10 _diffrn_reflns_limit_l_min -23 _diffrn_reflns_limit_l_max 24 _diffrn_reflns_theta_min 3.16 _diffrn_reflns_theta_max 28.40 _reflns_number_total 4233 _reflns_number_gt 4000 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Kuma KM4 software (1999)' _computing_cell_refinement 'Kuma KM4 software (1999)' _computing_data_reduction 'Kuma KM4 software (2000)' _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^)+(0.0309P)^2^+4.0379P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary vecmap _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 4233 _refine_ls_number_parameters 277 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0234 _refine_ls_R_factor_gt 0.0211 _refine_ls_wR_factor_ref 0.0565 _refine_ls_wR_factor_gt 0.0552 _refine_ls_goodness_of_fit_ref 0.989 _refine_ls_restrained_S_all 0.989 _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_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group Eu Eu 0.249029(10) 0.315066(13) 0.117634(6) 0.00770(5) Uani 1 d . . . O1 O 0.43910(16) 0.1995(2) 0.14699(10) 0.0138(4) Uani 1 d . . . O2 O 0.56242(16) 0.0653(2) 0.21646(10) 0.0166(4) Uani 1 d . . . O3 O 0.05384(16) 0.2163(2) 0.15426(10) 0.0134(4) Uani 1 d . . . O4 O -0.06720(16) 0.1010(2) 0.23158(10) 0.0171(4) Uani 1 d . . . O5 O 0.37405(16) 0.3567(2) 0.01626(10) 0.0125(4) Uani 1 d . . . O6 O 0.4529(2) 0.2819(3) -0.08777(11) 0.0252(5) Uani 1 d . . . O7 O 0.12574(16) 0.3369(2) 0.01464(10) 0.0116(3) Uani 1 d . . . O8 O 0.02514(18) 0.2273(2) -0.07492(11) 0.0194(4) Uani 1 d . . . OW1 O 0.11582(17) 0.5398(2) 0.12866(11) 0.0152(4) Uani 1 d . . . OW2 O 0.38112(18) 0.5325(2) 0.14033(11) 0.0164(4) Uani 1 d . . . OW3 O 0.24509(19) 0.3758(2) 0.24974(10) 0.0142(4) Uani 1 d . . . N1 N 0.24238(18) 0.0467(3) 0.19406(11) 0.0112(4) Uani 1 d . . . N2 N 0.25825(18) 0.0726(3) 0.03369(11) 0.0106(4) Uani 1 d . . . N11 N 0.7507(2) 0.2159(3) 0.14548(13) 0.0141(4) Uani 1 d . . . H11A H 0.6861 0.1722 0.1594 0.017 Uiso 1 calc R . . H11B H 0.8175 0.1886 0.1637 0.017 Uiso 1 calc R . . N12 N 0.84836(19) 0.3892(3) 0.07308(12) 0.0157(5) Uani 1 d . . . H12A H 0.8473 0.4579 0.0399 0.019 Uiso 1 calc R . . H12B H 0.9147 0.3611 0.0917 0.019 Uiso 1 calc R . . N13 N 0.6429(2) 0.3669(3) 0.06799(13) 0.0165(5) Uani 1 d . . . H13A H 0.5789 0.3224 0.0823 0.020 Uiso 1 calc R . . H13B H 0.6395 0.4378 0.0358 0.020 Uiso 1 calc R . . C1 C 0.4601(2) 0.1013(3) 0.19523(13) 0.0125(5) Uani 1 d . . . C2 C 0.3552(2) 0.0269(3) 0.23338(14) 0.0134(5) Uani 1 d . . . H2A H 0.3707 -0.0827 0.2394 0.016 Uiso 1 calc R . . H2B H 0.3473 0.0723 0.2805 0.016 Uiso 1 calc R . . C3 C 0.0349(2) 0.1275(3) 0.20682(14) 0.0124(5) Uani 1 d . . . C4 C 0.1403(2) 0.0528(3) 0.24368(14) 0.0140(5) Uani 1 d . . . H4A H 0.1615 0.1120 0.2858 0.017 Uiso 1 calc R . . H4B H 0.1195 -0.0511 0.2587 0.017 Uiso 1 calc R . . C5 C 0.2200(2) -0.0834(3) 0.14389(14) 0.0142(5) Uani 1 d . . . H5A H 0.1358 -0.0875 0.1333 0.017 Uiso 1 calc R . . H5B H 0.2414 -0.1796 0.1673 0.017 Uiso 1 calc R . . C6 C 0.2878(2) -0.0711(3) 0.07438(14) 0.0136(5) Uani 1 d . . . H6A H 0.3723 -0.0723 0.0845 0.016 Uiso 1 calc R . . H6B H 0.2699 -0.1605 0.0450 0.016 Uiso 1 calc R . . C7 C 0.3449(3) 0.0954(3) -0.02518(16) 0.0201(6) Uani 1 d . . . H7A H 0.3071 0.0664 -0.0698 0.024 Uiso 1 calc R . . H7B H 0.4110 0.0254 -0.0177 0.024 Uiso 1 calc R . . C8 C 0.3937(2) 0.2589(3) -0.03300(14) 0.0137(5) Uani 1 d . . . C9 C 0.1381(2) 0.0626(3) 0.00205(14) 0.0129(5) Uani 1 d . . . H9A H 0.0838 0.0205 0.0371 0.016 Uiso 1 calc R . . H9B H 0.1399 -0.0075 -0.0384 0.016 Uiso 1 calc R . . C10 C 0.0927(2) 0.2209(3) -0.02269(13) 0.0118(5) Uani 1 d . . . C11 C 0.7471(2) 0.3261(3) 0.09568(14) 0.0115(5) Uani 1 d . . . HW31 H 0.302(4) 0.399(6) 0.266(2) 0.040(13) Uiso 1 d . . . HW32 H 0.197(5) 0.429(7) 0.265(3) 0.066(17) Uiso 1 d . . . HW21 H 0.423(4) 0.582(6) 0.121(3) 0.053(15) Uiso 1 d . . . HW22 H 0.397(3) 0.549(5) 0.181(2) 0.027(10) Uiso 1 d . . . HW11 H 0.078(4) 0.597(5) 0.103(2) 0.029(10) Uiso 1 d . . . HW12 H 0.104(3) 0.569(4) 0.166(2) 0.017(9) Uiso 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 Eu 0.00666(7) 0.00914(7) 0.00729(7) 0.00094(4) -0.00059(4) -0.00071(4) O1 0.0083(8) 0.0178(10) 0.0154(9) 0.0058(7) 0.0007(7) -0.0006(7) O2 0.0085(8) 0.0249(10) 0.0165(9) 0.0070(8) -0.0006(7) 0.0015(8) O3 0.0107(8) 0.0160(9) 0.0134(9) 0.0058(7) -0.0010(7) -0.0011(7) O4 0.0091(8) 0.0252(11) 0.0169(9) 0.0073(8) -0.0001(7) -0.0018(8) O5 0.0121(8) 0.0147(9) 0.0108(8) 0.0009(7) 0.0004(7) -0.0024(7) O6 0.0324(12) 0.0234(11) 0.0198(10) -0.0045(8) 0.0154(9) -0.0106(10) O7 0.0122(8) 0.0113(8) 0.0113(8) 0.0006(6) -0.0021(7) 0.0006(7) O8 0.0220(10) 0.0163(9) 0.0199(10) 0.0006(8) -0.0127(8) 0.0000(8) OW1 0.0179(9) 0.0172(10) 0.0105(9) -0.0018(8) -0.0006(7) 0.0064(8) OW2 0.0182(10) 0.0191(10) 0.0121(9) -0.0005(8) -0.0012(8) -0.0090(8) OW3 0.0129(9) 0.0165(10) 0.0131(9) -0.0025(7) -0.0005(8) -0.0007(8) N1 0.0073(9) 0.0134(10) 0.0129(10) 0.0017(8) -0.0015(8) -0.0018(8) N2 0.0092(9) 0.0111(10) 0.0114(9) 0.0000(8) 0.0010(8) 0.0001(8) N11 0.0091(10) 0.0168(10) 0.0164(10) 0.0048(9) -0.0001(8) -0.0006(9) N12 0.0108(10) 0.0175(11) 0.0189(11) 0.0056(9) -0.0006(8) -0.0009(9) N13 0.0116(10) 0.0199(12) 0.0179(11) 0.0065(9) -0.0013(9) 0.0002(9) C1 0.0112(11) 0.0161(12) 0.0102(11) 0.0002(9) -0.0018(9) -0.0001(9) C2 0.0098(11) 0.0176(13) 0.0129(12) 0.0058(9) -0.0027(9) -0.0002(10) C3 0.0104(11) 0.0144(12) 0.0125(11) 0.0012(9) 0.0007(9) -0.0015(10) C4 0.0097(11) 0.0184(13) 0.0140(12) 0.0074(10) 0.0001(9) -0.0020(10) C5 0.0158(12) 0.0120(12) 0.0149(12) 0.0040(9) -0.0028(10) -0.0025(10) C6 0.0123(11) 0.0115(12) 0.0170(12) 0.0011(10) -0.0026(9) 0.0029(10) C7 0.0186(13) 0.0163(14) 0.0255(15) -0.0023(11) 0.0132(11) -0.0010(11) C8 0.0102(11) 0.0162(13) 0.0146(12) 0.0006(10) -0.0013(9) -0.0013(10) C9 0.0123(11) 0.0126(12) 0.0139(11) -0.0005(9) -0.0058(9) 0.0004(10) C10 0.0105(11) 0.0131(11) 0.0118(11) 0.0019(9) 0.0003(9) 0.0002(10) C11 0.0120(11) 0.0111(12) 0.0113(11) -0.0034(9) 0.0018(9) 0.0005(9) _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 Eu O7 2.383(2) . yes Eu O5 2.392(2) . yes Eu OW2 2.435(2) . yes Eu O1 2.426(2) . yes Eu O3 2.458(2) . yes Eu OW1 2.464(2) . yes Eu OW3 2.528(2) . yes Eu N2 2.622(2) . yes Eu N1 2.727(2) . yes Eu C10 3.264(3) . no O1 C1 1.262(3) . no O2 C1 1.258(3) . no O3 C3 1.266(3) . no O4 C3 1.262(3) . no O5 C8 1.271(3) . no O6 C8 1.240(3) . no O7 C10 1.278(3) . no O8 C10 1.240(3) . no N1 C2 1.478(3) . no N1 C5 1.487(3) . no N1 C4 1.480(3) . no N2 C9 1.479(3) . no N2 C6 1.495(3) . no N2 C7 1.487(3) . no N11 C11 1.333(3) . no N12 C11 1.335(3) . no N13 C11 1.331(4) . no C1 C2 1.525(3) . no C3 C4 1.517(4) . no C5 C6 1.514(4) . no C7 C8 1.524(4) . no C9 C10 1.532(4) . no 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 Eu O5 71.92(7) . . no O7 Eu OW2 115.83(7) . . no O5 Eu OW2 70.23(7) . . no O7 Eu O1 136.87(7) . . no O5 Eu O1 73.79(7) . . no OW2 Eu O1 74.88(7) . . no O7 Eu O3 74.46(7) . . no O5 Eu O3 143.30(7) . . no OW2 Eu O3 140.05(7) . . no O1 Eu O3 125.74(7) . . no O7 Eu OW1 69.55(7) . . no O5 Eu OW1 107.89(7) . . no OW2 Eu OW1 75.45(8) . . no O1 Eu OW1 147.52(7) . . no O3 Eu OW1 72.84(7) . . no O7 Eu OW3 139.82(7) . . no O5 Eu OW3 139.08(7) . . no OW2 Eu OW3 71.36(7) . . no O1 Eu OW3 83.14(8) . . no O3 Eu OW3 77.44(7) . . no OW1 Eu OW3 75.10(7) . . no O7 Eu N2 66.55(7) . . no O5 Eu N2 67.74(7) . . no OW2 Eu N2 134.21(7) . . no O1 Eu N2 76.75(7) . . no O3 Eu N2 85.73(7) . . no OW1 Eu N2 134.85(7) . . no OW3 Eu N2 138.84(7) . . no O7 Eu N1 118.40(6) . . no O5 Eu N1 124.11(7) . . no OW2 Eu N1 125.63(7) . . no O1 Eu N1 63.61(6) . . no O3 Eu N1 62.16(6) . . no OW1 Eu N1 127.58(7) . . no OW3 Eu N1 70.31(7) . . no N2 Eu N1 68.60(8) . . no O7 Eu C10 19.10(7) . . no O5 Eu C10 73.56(7) . . no OW2 Eu C10 131.47(7) . . no O1 Eu C10 123.70(7) . . no O3 Eu C10 69.85(7) . . no OW1 Eu C10 86.33(7) . . no OW3 Eu C10 145.97(7) . . no N2 Eu C10 48.70(7) . . no N1 Eu C10 101.23(7) . . no C1 O1 Eu 127.18(16) . . no C3 O3 Eu 125.40(16) . . no C8 O5 Eu 125.39(17) . . no C10 O7 Eu 123.31(17) . . no C2 N1 C5 111.8(2) . . no C2 N1 C4 111.1(2) . . no C5 N1 C4 106.9(2) . . no C2 N1 Eu 109.63(15) . . no C5 N1 Eu 108.50(15) . . no C4 N1 Eu 108.73(15) . . no C9 N2 C6 111.0(2) . . no C9 N2 C7 108.2(2) . . no C6 N2 C7 110.0(2) . . no C9 N2 Eu 104.45(15) . . no C6 N2 Eu 111.60(15) . . no C7 N2 Eu 111.38(16) . . no O2 C1 O1 124.3(2) . . no O2 C1 C2 117.3(2) . . no O1 C1 C2 118.3(2) . . no N1 C2 C1 112.6(2) . . no O3 C3 O4 123.4(2) . . no O3 C3 C4 118.6(2) . . no O4 C3 C4 118.0(2) . . no N1 C4 C3 109.8(2) . . no N1 C5 C6 113.8(2) . . no N2 C6 C5 112.6(2) . . no N2 C7 C8 115.6(2) . . no O6 C8 O5 126.0(3) . . no O6 C8 C7 115.0(2) . . no O5 C8 C7 118.9(2) . . no N2 C9 C10 112.0(2) . . no O8 C10 O7 125.0(3) . . no O8 C10 C9 118.9(2) . . no O7 C10 C9 116.1(2) . . no O8 C10 Eu 162.5(2) . . no O7 C10 Eu 37.59(12) . . no C9 C10 Eu 78.47(14) . . no N13 C11 N11 119.2(2) . . no N13 C11 N12 121.5(2) . . no N11 C11 N12 119.2(3) . . no _diffrn_measured_fraction_theta_max 0.924 _diffrn_reflns_theta_full 28.40 _diffrn_measured_fraction_theta_full 0.924 _refine_diff_density_max 0.823 _refine_diff_density_min -0.696 _refine_diff_density_rms 0.116