# Supplementary Material (ESI) for Dalton Transactions # This journal is (c) The Royal Society of Chemistry 2010 data_global _journal_coden_Cambridge 222 loop_ _publ_author_name 'Yan, Shi-Ping' _publ_contact_author_name 'Yan, Shi-Ping' _publ_contact_author_email yansp@nankai.edu.cn _publ_section_title ; Synthesis, DNA Binding, Photo-induced DNA Cleavage and Cytotoxicity Studies of Europium(III) Complexes ; # Attachment '- 1.cif' data_a _database_code_depnum_ccdc_archive 'CCDC 782173' #TrackingRef '- 1.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C29 H28 Eu N4 O6 ' _chemical_formula_weight 680.52 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 triclinic _symmetry_space_group_name_H-M p-1 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 9.5250(19) _cell_length_b 9.6630(19) _cell_length_c 16.224(3) _cell_angle_alpha 100.16(3) _cell_angle_beta 92.57(3) _cell_angle_gamma 99.41(3) _cell_volume 1445.9(5) _cell_formula_units_Z 2 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description prism _exptl_crystal_colour colorless _exptl_crystal_size_max 0.4 _exptl_crystal_size_mid 0.3 _exptl_crystal_size_min 0.2 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.563 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 682 _exptl_absorpt_coefficient_mu 2.217 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.455 _exptl_absorpt_correction_T_max 0.642 _exptl_absorpt_process_details crystalclear _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 'Bruker P4' _diffrn_measurement_method '\w scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 8546 _diffrn_reflns_av_R_equivalents 0.0760 _diffrn_reflns_av_sigmaI/netI 0.1457 _diffrn_reflns_limit_h_min -11 _diffrn_reflns_limit_h_max 10 _diffrn_reflns_limit_k_min -10 _diffrn_reflns_limit_k_max 11 _diffrn_reflns_limit_l_min -19 _diffrn_reflns_limit_l_max 19 _diffrn_reflns_theta_min 3.03 _diffrn_reflns_theta_max 25.30 _reflns_number_total 5220 _reflns_number_gt 3804 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker XSCANS' _computing_cell_refinement 'Bruker XSCANS' _computing_data_reduction 'Bruker SHELXTL' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0711P)^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_number_reflns 5220 _refine_ls_number_parameters 367 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.1293 _refine_ls_R_factor_gt 0.0842 _refine_ls_wR_factor_ref 0.1828 _refine_ls_wR_factor_gt 0.1657 _refine_ls_goodness_of_fit_ref 1.083 _refine_ls_restrained_S_all 1.083 _refine_ls_shift/su_max 0.013 _refine_ls_shift/su_mean 0.001 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 0.55734(6) 0.72317(6) 0.26768(3) 0.0420(2) Uani 1 1 d . . . O1 O 0.4712(8) 0.6597(9) 0.3922(5) 0.060(2) Uani 1 1 d . . . O2 O 0.4462(8) 0.9109(8) 0.3327(5) 0.055(2) Uani 1 1 d . . . O3 O 0.7430(9) 0.9251(8) 0.2949(6) 0.067(2) Uani 1 1 d . . . O4 O 0.7568(7) 0.6500(8) 0.3332(5) 0.050(2) Uani 1 1 d . . . O5 O 0.4751(8) 0.8157(8) 0.1517(5) 0.056(2) Uani 1 1 d . . . N1 N 0.2838(9) 0.6139(10) 0.2271(5) 0.045(2) Uani 1 1 d . . . N2 N 0.4813(9) 0.4402(9) 0.2347(5) 0.042(2) Uani 1 1 d . . . N3 N -0.0871(11) 0.1995(11) 0.1436(7) 0.068(3) Uani 1 1 d . . . N4 N 0.1154(11) 0.0195(11) 0.1523(7) 0.069(3) Uani 1 1 d . . . C1 C 0.1848(12) 0.6971(12) 0.2248(7) 0.053(3) Uani 1 1 d . . . H1 H 0.2145 0.7955 0.2365 0.064 Uiso 1 1 calc R . . C2 C 0.0433(12) 0.6455(13) 0.2062(7) 0.051(3) Uani 1 1 d . . . H2 H -0.0205 0.7087 0.2056 0.061 Uiso 1 1 calc R . . C3 C -0.0059(12) 0.5026(14) 0.1886(7) 0.056(3) Uani 1 1 d . . . C4 C 0.0923(11) 0.4085(12) 0.1908(6) 0.042(3) Uani 1 1 d . . . C5 C 0.0516(11) 0.2551(12) 0.1685(7) 0.047(3) Uani 1 1 d . . . C6 C -0.1229(16) 0.0579(17) 0.1260(9) 0.086(5) Uani 1 1 d . . . H6 H -0.2182 0.0157 0.1132 0.103 Uiso 1 1 calc R . . C7 C -0.0149(16) -0.0305(14) 0.1265(10) 0.086(5) Uani 1 1 d . . . H7 H -0.0411 -0.1283 0.1071 0.103 Uiso 1 1 calc R . . C8 C 0.1501(12) 0.1634(13) 0.1723(7) 0.052(3) Uani 1 1 d . . . C9 C 0.3044(11) 0.2247(12) 0.1976(7) 0.047(3) Uani 1 1 d . . . C10 C 0.4071(12) 0.1429(12) 0.2049(7) 0.051(3) Uani 1 1 d . . . H10 H 0.3828 0.0439 0.1932 0.062 Uiso 1 1 calc R . . C11 C 0.5411(14) 0.2042(13) 0.2287(8) 0.062(3) Uani 1 1 d . . . H11 H 0.6096 0.1490 0.2377 0.074 Uiso 1 1 calc R . . C12 C 0.5787(12) 0.3541(12) 0.2401(7) 0.052(3) Uani 1 1 d . . . H12 H 0.6743 0.3955 0.2519 0.063 Uiso 1 1 calc R . . C13 C 0.3453(10) 0.3762(11) 0.2139(6) 0.041(3) Uani 1 1 d . . . C14 C 0.2385(11) 0.4681(12) 0.2113(6) 0.046(3) Uani 1 1 d . . . C15 C 0.3504(17) 0.6143(17) 0.5123(9) 0.093(5) Uani 1 1 d . . . H15A H 0.2864 0.5293 0.4856 0.140 Uiso 1 1 calc R . . H15B H 0.3029 0.6680 0.5545 0.140 Uiso 1 1 calc R . . H15C H 0.4329 0.5888 0.5380 0.140 Uiso 1 1 calc R . . C16 C 0.3963(13) 0.7044(15) 0.4473(8) 0.062(3) Uani 1 1 d . . . C17 C 0.3513(13) 0.8380(14) 0.4541(8) 0.060(3) Uani 1 1 d . . . H17 H 0.2981 0.8645 0.4991 0.072 Uiso 1 1 calc R . . C18 C 0.3801(12) 0.9354(13) 0.3981(7) 0.054(3) Uani 1 1 d . . . C19 C 0.3233(14) 1.0738(14) 0.4110(8) 0.074(4) Uani 1 1 d . . . H19A H 0.3993 1.1512 0.4084 0.112 Uiso 1 1 calc R . . H19B H 0.2852 1.0890 0.4650 0.112 Uiso 1 1 calc R . . H19C H 0.2494 1.0692 0.3679 0.112 Uiso 1 1 calc R . . C20 C 0.3670(15) 0.8414(16) 0.0210(9) 0.085(5) Uani 1 1 d . . . H20A H 0.2875 0.8564 0.0538 0.127 Uiso 1 1 calc R . . H20B H 0.3345 0.7723 -0.0291 0.127 Uiso 1 1 calc R . . H20C H 0.4097 0.9298 0.0062 0.127 Uiso 1 1 calc R . . C21 C 0.4782(13) 0.7861(12) 0.0728(8) 0.054(3) Uani 1 1 d . . . C22 C 0.5753(14) 0.7106(15) 0.0298(8) 0.072(4) Uani 1 1 d . . . H22 H 0.5773 0.7064 -0.0278 0.087 Uiso 1 1 calc R . . C23 C 0.6699(11) 0.6410(13) 0.0699(8) 0.055(3) Uani 1 1 d . . . C24 C 0.7636(14) 0.5617(17) 0.0143(8) 0.085(5) Uani 1 1 d . . . H24A H 0.8571 0.6184 0.0181 0.128 Uiso 1 1 calc R . . H24B H 0.7234 0.5428 -0.0427 0.128 Uiso 1 1 calc R . . H24C H 0.7701 0.4730 0.0319 0.128 Uiso 1 1 calc R . . C25 C 0.9198(14) 1.1174(13) 0.3595(9) 0.078(4) Uani 1 1 d . . . H25A H 0.8572 1.1690 0.3342 0.116 Uiso 1 1 calc R . . H25B H 1.0091 1.1264 0.3340 0.116 Uiso 1 1 calc R . . H25C H 0.9361 1.1556 0.4186 0.116 Uiso 1 1 calc R . . C26 C 0.8511(13) 0.9589(12) 0.3463(8) 0.054(3) Uani 1 1 d . . . C27 C 0.9165(13) 0.8638(13) 0.3851(8) 0.060(3) Uani 1 1 d . . . H27 H 0.9997 0.9013 0.4195 0.072 Uiso 1 1 calc R . . C28 C 0.8664(12) 0.7194(14) 0.3758(7) 0.055(3) Uani 1 1 d . . . C29 C 0.9536(13) 0.6271(14) 0.4182(9) 0.072(4) Uani 1 1 d . . . H29A H 0.9241 0.6244 0.4738 0.108 Uiso 1 1 calc R . . H29B H 1.0532 0.6672 0.4213 0.108 Uiso 1 1 calc R . . H29C H 0.9378 0.5319 0.3858 0.108 Uiso 1 1 calc R . . O6 O 0.6851(8) 0.6411(9) 0.1468(5) 0.060(2) 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 0.0395(3) 0.0485(4) 0.0370(3) 0.0033(2) 0.0048(2) 0.0099(2) O1 0.053(5) 0.077(6) 0.053(5) 0.007(4) 0.018(4) 0.020(4) O2 0.060(5) 0.047(5) 0.058(5) 0.003(4) 0.014(4) 0.015(4) O3 0.053(5) 0.052(5) 0.089(7) 0.013(5) -0.008(5) -0.004(4) O4 0.039(4) 0.063(5) 0.046(4) 0.007(4) 0.002(4) 0.001(4) O5 0.072(6) 0.064(5) 0.040(5) 0.007(4) 0.006(4) 0.035(4) N1 0.034(5) 0.053(6) 0.047(5) 0.002(5) 0.006(4) 0.014(4) N2 0.037(5) 0.048(5) 0.043(5) 0.006(4) 0.007(4) 0.014(4) N3 0.056(7) 0.063(7) 0.084(8) 0.019(6) -0.016(6) 0.004(6) N4 0.063(7) 0.045(6) 0.090(8) 0.005(6) -0.009(6) -0.002(5) C1 0.058(8) 0.041(6) 0.064(8) 0.015(6) 0.015(6) 0.010(6) C2 0.039(7) 0.063(8) 0.056(8) 0.014(6) 0.009(5) 0.021(6) C3 0.038(7) 0.081(10) 0.054(8) 0.024(7) 0.002(6) 0.010(6) C4 0.034(6) 0.053(7) 0.042(6) 0.013(5) 0.006(5) 0.008(5) C5 0.032(6) 0.054(7) 0.059(8) 0.026(6) 0.011(5) 0.003(6) C6 0.076(10) 0.077(11) 0.094(12) 0.013(9) -0.024(9) -0.010(9) C7 0.081(11) 0.044(8) 0.121(14) 0.015(8) -0.013(10) -0.016(8) C8 0.048(7) 0.056(8) 0.048(7) 0.011(6) 0.000(5) 0.002(6) C9 0.041(6) 0.059(8) 0.045(7) 0.012(6) 0.004(5) 0.017(6) C10 0.049(7) 0.041(7) 0.060(8) 0.003(6) 0.000(6) 0.002(6) C11 0.077(10) 0.053(8) 0.060(8) 0.005(6) 0.006(7) 0.032(7) C12 0.046(7) 0.053(8) 0.057(8) 0.005(6) 0.006(6) 0.012(6) C13 0.032(6) 0.053(7) 0.040(6) 0.008(5) 0.005(5) 0.011(5) C14 0.047(7) 0.057(8) 0.036(6) 0.008(6) -0.001(5) 0.015(6) C15 0.108(12) 0.113(13) 0.081(11) 0.046(10) 0.047(9) 0.042(10) C16 0.054(8) 0.081(10) 0.055(8) 0.018(8) 0.004(6) 0.017(7) C17 0.059(8) 0.077(9) 0.048(8) 0.016(7) 0.020(6) 0.014(7) C18 0.044(7) 0.069(8) 0.046(7) -0.003(7) 0.001(6) 0.016(6) C19 0.070(9) 0.078(10) 0.071(9) -0.007(8) 0.013(7) 0.019(8) C20 0.090(11) 0.110(12) 0.061(9) 0.010(9) -0.016(8) 0.047(9) C21 0.064(8) 0.049(7) 0.048(8) 0.014(6) 0.006(6) 0.004(6) C22 0.064(9) 0.103(11) 0.048(8) 0.005(8) -0.001(7) 0.024(8) C23 0.038(7) 0.067(8) 0.055(8) -0.001(7) 0.011(6) 0.006(6) C24 0.069(9) 0.128(13) 0.054(8) -0.013(8) 0.013(7) 0.032(9) C25 0.081(10) 0.056(8) 0.088(11) -0.006(8) 0.005(8) 0.011(7) C26 0.049(7) 0.050(7) 0.059(8) -0.002(6) 0.012(6) 0.006(6) C27 0.052(8) 0.062(9) 0.057(8) -0.001(7) -0.006(6) 0.005(7) C28 0.039(7) 0.078(9) 0.044(7) 0.009(7) 0.007(5) 0.001(6) C29 0.063(9) 0.077(9) 0.073(9) 0.018(8) -0.015(7) 0.004(7) O6 0.059(5) 0.093(6) 0.034(5) 0.009(4) 0.017(4) 0.030(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 O1 2.357(8) . ? Eu1 O2 2.362(7) . ? Eu1 O3 2.372(8) . ? Eu1 O5 2.375(7) . ? Eu1 O4 2.400(7) . ? Eu1 O6 2.437(7) . ? Eu1 N1 2.653(8) . ? Eu1 N2 2.663(8) . ? O1 C16 1.231(14) . ? O2 C18 1.264(13) . ? O3 C26 1.257(13) . ? O4 C28 1.249(12) . ? O5 C21 1.265(13) . ? N1 C1 1.338(13) . ? N1 C14 1.379(14) . ? N2 C13 1.342(12) . ? N2 C12 1.353(13) . ? N3 C6 1.331(16) . ? N3 C5 1.357(13) . ? N4 C7 1.278(15) . ? N4 C8 1.352(14) . ? C1 C2 1.359(15) . ? C1 H1 0.9300 . ? C2 C3 1.358(16) . ? C2 H2 0.9300 . ? C3 C4 1.410(15) . ? C4 C14 1.418(14) . ? C4 C5 1.445(15) . ? C5 C8 1.398(15) . ? C6 C7 1.442(19) . ? C6 H6 0.9300 . ? C7 H7 0.9300 . ? C8 C9 1.502(15) . ? C9 C10 1.367(14) . ? C9 C13 1.425(15) . ? C10 C11 1.325(16) . ? C10 H10 0.9300 . ? C11 C12 1.411(16) . ? C11 H11 0.9300 . ? C12 H12 0.9300 . ? C13 C14 1.459(14) . ? C15 C16 1.518(18) . ? C15 H15A 0.9600 . ? C15 H15B 0.9600 . ? C15 H15C 0.9600 . ? C16 C17 1.413(17) . ? C17 C18 1.423(17) . ? C17 H17 0.9300 . ? C18 C19 1.508(16) . ? C19 H19A 0.9600 . ? C19 H19B 0.9600 . ? C19 H19C 0.9600 . ? C20 C21 1.541(16) . ? C20 H20A 0.9600 . ? C20 H20B 0.9600 . ? C20 H20C 0.9600 . ? C21 C22 1.405(17) . ? C22 C23 1.410(17) . ? C22 H22 0.9300 . ? C23 O6 1.249(13) . ? C23 C24 1.500(16) . ? C24 H24A 0.9600 . ? C24 H24B 0.9600 . ? C24 H24C 0.9600 . ? C25 C26 1.537(16) . ? C25 H25A 0.9600 . ? C25 H25B 0.9600 . ? C25 H25C 0.9600 . ? C26 C27 1.408(16) . ? C27 C28 1.378(17) . ? C27 H27 0.9300 . ? C28 C29 1.538(16) . ? C29 H29A 0.9600 . ? C29 H29B 0.9600 . ? C29 H29C 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 O1 Eu1 O2 73.0(3) . . ? O1 Eu1 O3 112.1(3) . . ? O2 Eu1 O3 75.7(3) . . ? O1 Eu1 O5 138.4(3) . . ? O2 Eu1 O5 77.3(3) . . ? O3 Eu1 O5 87.3(3) . . ? O1 Eu1 O4 76.1(3) . . ? O2 Eu1 O4 123.2(3) . . ? O3 Eu1 O4 73.5(3) . . ? O5 Eu1 O4 145.4(3) . . ? O1 Eu1 O6 142.7(3) . . ? O2 Eu1 O6 144.3(3) . . ? O3 Eu1 O6 85.6(3) . . ? O5 Eu1 O6 71.6(3) . . ? O4 Eu1 O6 78.3(3) . . ? O1 Eu1 N1 75.5(3) . . ? O2 Eu1 N1 78.6(3) . . ? O3 Eu1 N1 149.3(3) . . ? O5 Eu1 N1 70.6(3) . . ? O4 Eu1 N1 136.0(3) . . ? O6 Eu1 N1 106.4(3) . . ? O1 Eu1 N2 74.1(3) . . ? O2 Eu1 N2 133.5(3) . . ? O3 Eu1 N2 148.4(3) . . ? O5 Eu1 N2 108.6(3) . . ? O4 Eu1 N2 78.4(2) . . ? O6 Eu1 N2 74.5(3) . . ? N1 Eu1 N2 61.8(3) . . ? C16 O1 Eu1 137.9(9) . . ? C18 O2 Eu1 135.8(8) . . ? C26 O3 Eu1 132.3(8) . . ? C28 O4 Eu1 132.0(8) . . ? C21 O5 Eu1 135.8(8) . . ? C1 N1 C14 117.8(9) . . ? C1 N1 Eu1 121.7(7) . . ? C14 N1 Eu1 120.4(6) . . ? C13 N2 C12 116.9(9) . . ? C13 N2 Eu1 122.0(7) . . ? C12 N2 Eu1 121.1(7) . . ? C6 N3 C5 117.3(11) . . ? C7 N4 C8 115.9(11) . . ? N1 C1 C2 123.6(11) . . ? N1 C1 H1 118.2 . . ? C2 C1 H1 118.2 . . ? C3 C2 C1 120.6(11) . . ? C3 C2 H2 119.7 . . ? C1 C2 H2 119.7 . . ? C2 C3 C4 118.9(10) . . ? C3 C4 C14 118.2(10) . . ? C3 C4 C5 123.0(10) . . ? C14 C4 C5 118.8(10) . . ? N3 C5 C8 119.5(10) . . ? N3 C5 C4 118.4(10) . . ? C8 C5 C4 122.2(9) . . ? N3 C6 C7 120.4(12) . . ? N3 C6 H6 119.8 . . ? C7 C6 H6 119.8 . . ? N4 C7 C6 122.9(12) . . ? N4 C7 H7 118.5 . . ? C6 C7 H7 118.5 . . ? N4 C8 C5 123.6(10) . . ? N4 C8 C9 116.8(10) . . ? C5 C8 C9 119.6(10) . . ? C10 C9 C13 118.7(10) . . ? C10 C9 C8 123.4(11) . . ? C13 C9 C8 117.8(9) . . ? C11 C10 C9 120.3(11) . . ? C11 C10 H10 119.8 . . ? C9 C10 H10 119.8 . . ? C10 C11 C12 119.2(11) . . ? C10 C11 H11 120.4 . . ? C12 C11 H11 120.4 . . ? N2 C12 C11 122.8(11) . . ? N2 C12 H12 118.6 . . ? C11 C12 H12 118.6 . . ? N2 C13 C9 121.9(9) . . ? N2 C13 C14 117.3(9) . . ? C9 C13 C14 120.7(9) . . ? N1 C14 C4 120.9(10) . . ? N1 C14 C13 118.4(9) . . ? C4 C14 C13 120.7(10) . . ? C16 C15 H15A 109.5 . . ? C16 C15 H15B 109.5 . . ? H15A C15 H15B 109.5 . . ? C16 C15 H15C 109.5 . . ? H15A C15 H15C 109.5 . . ? H15B C15 H15C 109.5 . . ? O1 C16 C17 123.2(13) . . ? O1 C16 C15 119.4(12) . . ? C17 C16 C15 117.4(12) . . ? C16 C17 C18 125.7(12) . . ? C16 C17 H17 117.1 . . ? C18 C17 H17 117.1 . . ? O2 C18 C17 124.0(11) . . ? O2 C18 C19 115.1(12) . . ? C17 C18 C19 120.8(11) . . ? C18 C19 H19A 109.5 . . ? C18 C19 H19B 109.5 . . ? H19A C19 H19B 109.5 . . ? C18 C19 H19C 109.5 . . ? H19A C19 H19C 109.5 . . ? H19B C19 H19C 109.5 . . ? C21 C20 H20A 109.5 . . ? C21 C20 H20B 109.5 . . ? H20A C20 H20B 109.5 . . ? C21 C20 H20C 109.5 . . ? H20A C20 H20C 109.5 . . ? H20B C20 H20C 109.5 . . ? O5 C21 C22 125.4(11) . . ? O5 C21 C20 116.1(11) . . ? C22 C21 C20 118.5(11) . . ? C21 C22 C23 123.1(12) . . ? C21 C22 H22 118.4 . . ? C23 C22 H22 118.4 . . ? O6 C23 C22 126.6(11) . . ? O6 C23 C24 117.1(11) . . ? C22 C23 C24 116.2(12) . . ? C23 C24 H24A 109.5 . . ? C23 C24 H24B 109.5 . . ? H24A C24 H24B 109.5 . . ? C23 C24 H24C 109.5 . . ? H24A C24 H24C 109.5 . . ? H24B C24 H24C 109.5 . . ? C26 C25 H25A 109.5 . . ? C26 C25 H25B 109.5 . . ? H25A C25 H25B 109.5 . . ? C26 C25 H25C 109.5 . . ? H25A C25 H25C 109.5 . . ? H25B C25 H25C 109.5 . . ? O3 C26 C27 125.8(11) . . ? O3 C26 C25 114.1(11) . . ? C27 C26 C25 120.0(11) . . ? C28 C27 C26 124.8(11) . . ? C28 C27 H27 117.6 . . ? C26 C27 H27 117.6 . . ? O4 C28 C27 127.1(12) . . ? O4 C28 C29 113.8(11) . . ? C27 C28 C29 119.1(10) . . ? C28 C29 H29A 109.5 . . ? C28 C29 H29B 109.5 . . ? H29A C29 H29B 109.5 . . ? C28 C29 H29C 109.5 . . ? H29A C29 H29C 109.5 . . ? H29B C29 H29C 109.5 . . ? C23 O6 Eu1 134.5(7) . . ? _diffrn_measured_fraction_theta_max 0.989 _diffrn_reflns_theta_full 25.30 _diffrn_measured_fraction_theta_full 0.989 _refine_diff_density_max 1.857 _refine_diff_density_min -2.122 _refine_diff_density_rms 0.170 # Attachment '- 2.cif' data_a2 _database_code_depnum_ccdc_archive 'CCDC 782174' #TrackingRef '- 2.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C34 H33 Eu N4 O7 ' _chemical_formula_weight 761.61 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' Cl Cl 0.1484 0.1585 '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 Triclinic _symmetry_space_group_name_H-M P-1 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 9.6910(19) _cell_length_b 12.743(3) _cell_length_c 13.705(3) _cell_angle_alpha 76.73(3) _cell_angle_beta 80.20(3) _cell_angle_gamma 88.54(3) _cell_volume 1623.1(6) _cell_formula_units_Z 2 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min 24 _cell_measurement_theta_max 79 _exptl_crystal_description prism _exptl_crystal_colour colorless _exptl_crystal_size_max 0.4 _exptl_crystal_size_mid 0.31 _exptl_crystal_size_min 0.21 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.558 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 768 _exptl_absorpt_coefficient_mu 1.986 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.482 _exptl_absorpt_correction_T_max 0.659 _exptl_absorpt_process_details crystalclear _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 'Bruker P4' _diffrn_measurement_method '\w scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 11712 _diffrn_reflns_av_R_equivalents 0.0293 _diffrn_reflns_av_sigmaI/netI 0.0517 _diffrn_reflns_limit_h_min -12 _diffrn_reflns_limit_h_max 12 _diffrn_reflns_limit_k_min -16 _diffrn_reflns_limit_k_max 16 _diffrn_reflns_limit_l_min -16 _diffrn_reflns_limit_l_max 17 _diffrn_reflns_theta_min 3.08 _diffrn_reflns_theta_max 27.48 _reflns_number_total 7446 _reflns_number_gt 6370 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker XSCANS' _computing_cell_refinement 'Bruker XSCANS' _computing_data_reduction 'Bruker SHELXTL' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0558P)^2^+0.3636P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 7276 _refine_ls_number_parameters 422 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0543 _refine_ls_R_factor_gt 0.0435 _refine_ls_wR_factor_ref 0.1141 _refine_ls_wR_factor_gt 0.1071 _refine_ls_goodness_of_fit_ref 1.157 _refine_ls_restrained_S_all 1.157 _refine_ls_shift/su_max 0.069 _refine_ls_shift/su_mean 0.009 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 C10 C 1.3585(5) -0.0016(5) -0.0791(4) 0.0500(14) Uani 1 1 d . . . H10 H 1.3796 0.0601 -0.1309 0.060 Uiso 1 1 calc R . . H9 H 1.5084 -0.0922 -0.1336 0.060 Uiso 1 1 d R . . C9 C 1.4344(5) -0.0924(6) -0.0803(4) 0.0569(15) Uani 1 1 d . . . Eu1 Eu 0.60020(2) 0.265866(19) 0.332709(16) 0.03227(9) Uani 1 1 d . . . O1 O 0.4051(3) 0.1507(3) 0.3481(3) 0.0467(9) Uani 1 1 d . . . O2 O 0.4865(3) 0.3308(3) 0.1913(3) 0.0517(9) Uani 1 1 d . . . O3 O 0.4344(4) 0.3607(3) 0.4239(3) 0.0524(9) Uani 1 1 d . . . O4 O 0.6610(4) 0.4513(3) 0.2762(3) 0.0513(9) Uani 1 1 d . . . O5 O 0.8207(3) 0.2852(3) 0.3793(3) 0.0503(9) Uani 1 1 d . . . O6 O 0.5845(3) 0.1739(3) 0.5041(2) 0.0440(8) Uani 1 1 d . . . N1 N 0.7219(4) 0.0825(3) 0.3163(3) 0.0326(8) Uani 1 1 d . . . N2 N 0.7872(4) 0.2648(3) 0.1710(3) 0.0336(8) Uani 1 1 d . . . N3 N 1.1041(4) -0.1023(3) 0.1565(3) 0.0396(9) Uani 1 1 d . . . N4 N 1.1693(4) 0.0877(4) 0.0030(3) 0.0389(9) Uani 1 1 d . . . C1 C 0.6846(5) -0.0094(4) 0.3869(4) 0.0400(11) Uani 1 1 d . . . H1 H 0.6110 -0.0074 0.4397 0.048 Uiso 1 1 calc R . . C2 C 0.7510(5) -0.1066(4) 0.3844(4) 0.0433(12) Uani 1 1 d . . . H2 H 0.7188 -0.1690 0.4324 0.052 Uiso 1 1 calc R . . C3 C 0.8640(5) -0.1097(4) 0.3107(4) 0.0409(11) Uani 1 1 d . . . H3 H 0.9114 -0.1738 0.3092 0.049 Uiso 1 1 calc R . . C4 C 0.9081(4) -0.0153(4) 0.2371(3) 0.0333(10) Uani 1 1 d . . . C5 C 1.0290(4) -0.0132(4) 0.1566(3) 0.0326(10) Uani 1 1 d . . . C6 C 1.2137(5) -0.0970(5) 0.0798(4) 0.0406(12) Uani 1 1 d . . . C7 C 1.2980(5) -0.1888(5) 0.0765(4) 0.0513(14) Uani 1 1 d . . . H7 H 1.2813 -0.2509 0.1283 0.062 Uiso 1 1 calc R . . C8 C 1.4044(6) -0.1853(5) -0.0040(5) 0.0573(15) Uani 1 1 d . . . H8 H 1.4577 -0.2464 -0.0077 0.069 Uiso 1 1 calc R . . C11 C 1.2459(5) -0.0024(4) 0.0029(4) 0.0404(11) Uani 1 1 d . . . C12 C 1.0630(4) 0.0827(4) 0.0800(3) 0.0340(10) Uani 1 1 d . . . C13 C 0.9787(4) 0.1780(4) 0.0831(3) 0.0329(10) Uani 1 1 d . . . C14 C 1.0041(5) 0.2739(4) 0.0088(4) 0.0432(12) Uani 1 1 d . . . H14 H 1.0780 0.2781 -0.0451 0.052 Uiso 1 1 calc R . . C15 C 0.9217(5) 0.3617(4) 0.0143(4) 0.0455(12) Uani 1 1 d . . . H15 H 0.9372 0.4251 -0.0359 0.055 Uiso 1 1 calc R . . C16 C 0.8136(5) 0.3537(4) 0.0973(4) 0.0428(11) Uani 1 1 d . . . H16 H 0.7574 0.4133 0.1013 0.051 Uiso 1 1 calc R . . C17 C 0.8676(4) 0.1767(4) 0.1638(3) 0.0314(9) Uani 1 1 d . . . C18 C 0.8322(4) 0.0792(4) 0.2424(3) 0.0296(9) Uani 1 1 d . . . C19 C 0.3185(7) 0.4123(8) 0.0916(6) 0.100(3) Uani 1 1 d . . . H19A H 0.2969 0.4781 0.1134 0.150 Uiso 1 1 calc R . . H19B H 0.2373 0.3870 0.0718 0.150 Uiso 1 1 calc R . . H19C H 0.3938 0.4253 0.0346 0.150 Uiso 1 1 calc R . . C20 C 0.3625(6) 0.3267(5) 0.1794(4) 0.0531(15) Uani 1 1 d . . . C21 C 0.2639(6) 0.2490(6) 0.2360(5) 0.0583(16) Uani 1 1 d . . . C22 C 0.2901(5) 0.1656(5) 0.3129(4) 0.0480(13) Uani 1 1 d . . . C23 C 0.1746(6) 0.0834(6) 0.3641(6) 0.0716(19) Uani 1 1 d . . . H23A H 0.1871 0.0531 0.4329 0.107 Uiso 1 1 calc R . . H23B H 0.1783 0.0271 0.3277 0.107 Uiso 1 1 calc R . . H23C H 0.0854 0.1179 0.3641 0.107 Uiso 1 1 calc R . . C24 C 0.6477(9) 0.6376(5) 0.1974(6) 0.093(3) Uani 1 1 d . . . H24A H 0.7258 0.6651 0.2189 0.140 Uiso 1 1 calc R . . H24B H 0.5762 0.6911 0.1914 0.140 Uiso 1 1 calc R . . H24C H 0.6779 0.6201 0.1326 0.140 Uiso 1 1 calc R . . C25 C 0.5889(6) 0.5358(5) 0.2758(4) 0.0522(14) Uani 1 1 d . . . C26 C 0.4628(6) 0.5421(5) 0.3377(5) 0.0613(16) Uani 1 1 d . . . H26 H 0.4175 0.6080 0.3286 0.074 Uiso 1 1 calc R . . C27 C 0.3976(5) 0.4563(5) 0.4135(5) 0.0492(13) Uani 1 1 d . . . C28 C 0.2786(6) 0.4798(5) 0.4912(5) 0.0674(19) Uani 1 1 d . . . H28A H 0.2522 0.4152 0.5425 0.101 Uiso 1 1 calc R . . H28B H 0.2000 0.5052 0.4585 0.101 Uiso 1 1 calc R . . H28C H 0.3076 0.5341 0.5220 0.101 Uiso 1 1 calc R . . C29 C 1.0099(6) 0.3105(5) 0.4610(5) 0.0599(16) Uani 1 1 d . . . H29A H 1.0697 0.3017 0.4000 0.090 Uiso 1 1 calc R . . H29B H 1.0470 0.2711 0.5191 0.090 Uiso 1 1 calc R . . H29C H 1.0055 0.3856 0.4620 0.090 Uiso 1 1 calc R . . C30 C 0.8653(5) 0.2685(4) 0.4637(4) 0.0410(11) Uani 1 1 d . . . C31 C 0.7904(6) 0.2186(5) 0.5584(4) 0.0497(13) Uani 1 1 d . . . H31 H 0.8331 0.2132 0.6151 0.060 Uiso 1 1 calc R . . C32 C 0.6549(5) 0.1762(4) 0.5732(4) 0.0415(11) Uani 1 1 d . . . C33 C 0.5862(6) 0.1271(5) 0.6823(4) 0.0588(15) Uani 1 1 d . . . H33A H 0.5031 0.1663 0.6995 0.088 Uiso 1 1 calc R . . H33B H 0.6503 0.1312 0.7276 0.088 Uiso 1 1 calc R . . H33C H 0.5619 0.0531 0.6884 0.088 Uiso 1 1 calc R . . O7 O -0.0299(6) 0.4929(6) 0.2143(4) 0.1009(19) Uani 1 1 d . . . C34 C 0.0183(13) 0.5659(10) 0.2653(7) 0.146(5) Uani 1 1 d . . . H34A H -0.0477 0.5675 0.3257 0.219 Uiso 1 1 calc R . . H34B H 0.0277 0.6368 0.2214 0.219 Uiso 1 1 calc R . . H34C H 0.1075 0.5431 0.2835 0.219 Uiso 1 1 calc 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 C10 0.037(3) 0.072(4) 0.039(3) -0.017(3) 0.004(2) 0.001(3) C9 0.041(3) 0.081(5) 0.055(3) -0.035(3) 0.003(2) 0.008(3) Eu1 0.03202(13) 0.03325(14) 0.03179(14) -0.01029(9) -0.00235(9) 0.00170(9) O1 0.0390(18) 0.038(2) 0.068(2) -0.0180(18) -0.0163(17) 0.0008(15) O2 0.0398(19) 0.070(3) 0.044(2) -0.0091(19) -0.0093(16) 0.0104(17) O3 0.055(2) 0.042(2) 0.056(2) -0.0208(18) 0.0117(18) 0.0043(17) O4 0.057(2) 0.038(2) 0.053(2) -0.0113(17) 0.0061(18) -0.0020(17) O5 0.0390(18) 0.064(3) 0.045(2) -0.0078(18) -0.0054(16) -0.0056(17) O6 0.0426(18) 0.054(2) 0.0327(17) -0.0053(16) -0.0047(15) -0.0077(16) N1 0.0322(18) 0.036(2) 0.0276(18) -0.0064(16) -0.0019(15) 0.0018(16) N2 0.0365(19) 0.031(2) 0.0322(19) -0.0063(16) -0.0055(16) 0.0059(16) N3 0.038(2) 0.042(2) 0.038(2) -0.0113(18) -0.0032(17) 0.0080(17) N4 0.035(2) 0.049(3) 0.034(2) -0.0135(19) -0.0031(16) 0.0015(18) C1 0.035(2) 0.042(3) 0.038(3) -0.006(2) 0.003(2) -0.002(2) C2 0.047(3) 0.037(3) 0.038(3) 0.002(2) -0.001(2) 0.006(2) C3 0.043(3) 0.036(3) 0.041(3) -0.006(2) -0.005(2) 0.011(2) C4 0.033(2) 0.037(3) 0.029(2) -0.0064(19) -0.0044(18) 0.0041(19) C5 0.032(2) 0.040(3) 0.029(2) -0.013(2) -0.0095(18) 0.0074(19) C6 0.034(2) 0.056(3) 0.037(3) -0.018(2) -0.012(2) 0.010(2) C7 0.048(3) 0.052(3) 0.056(3) -0.021(3) -0.005(2) 0.014(2) C8 0.050(3) 0.069(4) 0.061(4) -0.032(3) -0.009(3) 0.020(3) C11 0.032(2) 0.053(3) 0.041(3) -0.024(2) -0.005(2) 0.006(2) C12 0.030(2) 0.039(3) 0.034(2) -0.012(2) -0.0034(18) 0.0003(18) C13 0.033(2) 0.037(3) 0.029(2) -0.0076(19) -0.0052(17) 0.0012(18) C14 0.042(3) 0.047(3) 0.037(3) -0.009(2) 0.006(2) -0.004(2) C15 0.058(3) 0.037(3) 0.036(3) -0.002(2) -0.002(2) -0.001(2) C16 0.045(3) 0.037(3) 0.043(3) -0.009(2) 0.001(2) 0.003(2) C17 0.030(2) 0.034(2) 0.031(2) -0.0094(19) -0.0038(17) -0.0009(18) C18 0.028(2) 0.034(2) 0.026(2) -0.0041(18) -0.0062(16) 0.0015(17) C19 0.063(4) 0.138(8) 0.079(5) 0.016(5) -0.017(4) 0.034(5) C20 0.048(3) 0.076(4) 0.038(3) -0.018(3) -0.012(2) 0.025(3) C21 0.040(3) 0.078(5) 0.061(4) -0.019(3) -0.015(3) 0.010(3) C22 0.044(3) 0.053(3) 0.055(3) -0.027(3) -0.012(2) 0.004(2) C23 0.049(3) 0.070(5) 0.107(6) -0.034(4) -0.024(4) -0.005(3) C24 0.119(6) 0.041(4) 0.094(6) 0.001(4) 0.030(5) 0.003(4) C25 0.064(3) 0.037(3) 0.053(3) -0.010(3) -0.004(3) 0.002(3) C26 0.065(4) 0.040(3) 0.073(4) -0.012(3) 0.004(3) 0.012(3) C27 0.040(3) 0.050(3) 0.066(4) -0.035(3) -0.003(2) 0.001(2) C28 0.041(3) 0.064(4) 0.104(5) -0.052(4) 0.012(3) 0.000(3) C29 0.047(3) 0.064(4) 0.072(4) -0.012(3) -0.023(3) -0.001(3) C30 0.043(3) 0.032(3) 0.049(3) -0.010(2) -0.010(2) 0.004(2) C31 0.051(3) 0.053(3) 0.048(3) -0.009(3) -0.021(2) -0.002(2) C32 0.053(3) 0.033(3) 0.040(3) -0.014(2) -0.003(2) 0.007(2) C33 0.071(4) 0.065(4) 0.036(3) -0.003(3) -0.009(3) -0.003(3) O7 0.098(4) 0.134(5) 0.067(3) -0.021(3) 0.000(3) -0.039(4) C34 0.180(11) 0.149(11) 0.090(7) -0.014(7) 0.024(7) -0.065(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 C10 C9 1.357(8) . ? C10 C11 1.426(6) . ? C10 H10 0.9300 . ? C9 C8 1.387(9) . ? C9 H9 0.9323 . ? Eu1 O3 2.349(3) . ? Eu1 O6 2.353(3) . ? Eu1 O2 2.366(3) . ? Eu1 O5 2.366(3) . ? Eu1 O4 2.368(4) . ? Eu1 O1 2.374(3) . ? Eu1 N2 2.615(4) . ? Eu1 N1 2.629(4) . ? O1 C22 1.281(6) . ? O2 C20 1.244(6) . ? O3 C27 1.243(7) . ? O4 C25 1.269(6) . ? O5 C30 1.274(6) . ? O6 C32 1.265(6) . ? N1 C18 1.348(5) . ? N1 C1 1.349(6) . ? N2 C16 1.330(6) . ? N2 C17 1.364(6) . ? N3 C5 1.333(6) . ? N3 C6 1.352(6) . ? N4 C12 1.335(6) . ? N4 C11 1.351(6) . ? C1 C2 1.386(7) . ? C1 H1 0.9300 . ? C2 C3 1.364(6) . ? C2 H2 0.9300 . ? C3 C4 1.404(7) . ? C3 H3 0.9300 . ? C4 C18 1.404(6) . ? C4 C5 1.462(6) . ? C5 C12 1.420(7) . ? C6 C11 1.409(8) . ? C6 C7 1.415(7) . ? C7 C8 1.370(7) . ? C7 H7 0.9300 . ? C8 H8 0.9300 . ? C12 C13 1.451(6) . ? C13 C14 1.396(7) . ? C13 C17 1.403(6) . ? C14 C15 1.367(7) . ? C14 H14 0.9300 . ? C15 C16 1.396(7) . ? C15 H15 0.9300 . ? C16 H16 0.9300 . ? C17 C18 1.451(6) . ? C19 C20 1.539(9) . ? C19 H19A 0.9600 . ? C19 H19B 0.9600 . ? C19 H19C 0.9600 . ? C20 C21 1.393(9) . ? C21 C22 1.366(8) . ? C22 C23 1.515(8) . ? C23 H23A 0.9600 . ? C23 H23B 0.9600 . ? C23 H23C 0.9600 . ? C24 C25 1.533(8) . ? C24 H24A 0.9600 . ? C24 H24B 0.9600 . ? C24 H24C 0.9600 . ? C25 C26 1.375(8) . ? C26 C27 1.402(8) . ? C26 H26 0.9300 . ? C27 C28 1.505(7) . ? C28 H28A 0.9600 . ? C28 H28B 0.9600 . ? C28 H28C 0.9600 . ? C29 C30 1.505(7) . ? C29 H29A 0.9600 . ? C29 H29B 0.9600 . ? C29 H29C 0.9600 . ? C30 C31 1.392(7) . ? C31 C32 1.397(7) . ? C31 H31 0.9300 . ? C32 C33 1.524(7) . ? C33 H33A 0.9600 . ? C33 H33B 0.9600 . ? C33 H33C 0.9600 . ? O7 C34 1.417(11) . ? C34 H34A 0.9600 . ? C34 H34B 0.9600 . ? C34 H34C 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 C9 C10 C11 118.8(6) . . ? C9 C10 H10 120.6 . . ? C11 C10 H10 120.6 . . ? C10 C9 C8 121.5(5) . . ? C10 C9 H9 119.1 . . ? C8 C9 H9 119.4 . . ? O3 Eu1 O6 74.82(13) . . ? O3 Eu1 O2 87.12(13) . . ? O6 Eu1 O2 148.48(12) . . ? O3 Eu1 O5 108.41(14) . . ? O6 Eu1 O5 73.10(12) . . ? O2 Eu1 O5 138.03(13) . . ? O3 Eu1 O4 72.60(13) . . ? O6 Eu1 O4 122.17(13) . . ? O2 Eu1 O4 74.40(14) . . ? O5 Eu1 O4 73.78(14) . . ? O3 Eu1 O1 82.70(13) . . ? O6 Eu1 O1 80.14(13) . . ? O2 Eu1 O1 71.98(13) . . ? O5 Eu1 O1 146.63(13) . . ? O4 Eu1 O1 138.89(13) . . ? O3 Eu1 N2 149.03(13) . . ? O6 Eu1 N2 132.41(12) . . ? O2 Eu1 N2 73.78(12) . . ? O5 Eu1 N2 73.79(12) . . ? O4 Eu1 N2 78.81(12) . . ? O1 Eu1 N2 112.92(13) . . ? O3 Eu1 N1 148.94(12) . . ? O6 Eu1 N1 78.05(12) . . ? O2 Eu1 N1 109.32(13) . . ? O5 Eu1 N1 77.26(13) . . ? O4 Eu1 N1 136.30(12) . . ? O1 Eu1 N1 78.01(12) . . ? N2 Eu1 N1 61.96(12) . . ? C22 O1 Eu1 132.3(4) . . ? C20 O2 Eu1 132.6(4) . . ? C27 O3 Eu1 135.4(4) . . ? C25 O4 Eu1 132.0(4) . . ? C30 O5 Eu1 134.2(3) . . ? C32 O6 Eu1 134.3(3) . . ? C18 N1 C1 117.7(4) . . ? C18 N1 Eu1 121.0(3) . . ? C1 N1 Eu1 121.0(3) . . ? C16 N2 C17 118.3(4) . . ? C16 N2 Eu1 120.4(3) . . ? C17 N2 Eu1 121.1(3) . . ? C5 N3 C6 116.8(4) . . ? C12 N4 C11 116.6(4) . . ? N1 C1 C2 123.0(4) . . ? N1 C1 H1 118.5 . . ? C2 C1 H1 118.5 . . ? C3 C2 C1 119.2(5) . . ? C3 C2 H2 120.4 . . ? C1 C2 H2 120.4 . . ? C2 C3 C4 119.5(4) . . ? C2 C3 H3 120.3 . . ? C4 C3 H3 120.3 . . ? C3 C4 C18 117.9(4) . . ? C3 C4 C5 122.1(4) . . ? C18 C4 C5 120.0(4) . . ? N3 C5 C12 121.5(4) . . ? N3 C5 C4 118.9(4) . . ? C12 C5 C4 119.6(4) . . ? N3 C6 C11 121.6(4) . . ? N3 C6 C7 119.2(5) . . ? C11 C6 C7 119.1(5) . . ? C8 C7 C6 119.2(6) . . ? C8 C7 H7 120.4 . . ? C6 C7 H7 120.4 . . ? C7 C8 C9 121.4(5) . . ? C7 C8 H8 119.3 . . ? C9 C8 H8 119.3 . . ? N4 C11 C6 121.5(4) . . ? N4 C11 C10 118.5(5) . . ? C6 C11 C10 119.9(5) . . ? N4 C12 C5 121.9(4) . . ? N4 C12 C13 118.2(4) . . ? C5 C12 C13 119.8(4) . . ? C14 C13 C17 117.3(4) . . ? C14 C13 C12 122.7(4) . . ? C17 C13 C12 120.0(4) . . ? C15 C14 C13 120.8(4) . . ? C15 C14 H14 119.6 . . ? C13 C14 H14 119.6 . . ? C14 C15 C16 118.3(5) . . ? C14 C15 H15 120.9 . . ? C16 C15 H15 120.9 . . ? N2 C16 C15 123.1(5) . . ? N2 C16 H16 118.4 . . ? C15 C16 H16 118.4 . . ? N2 C17 C13 122.2(4) . . ? N2 C17 C18 117.2(4) . . ? C13 C17 C18 120.6(4) . . ? N1 C18 C4 122.5(4) . . ? N1 C18 C17 117.6(4) . . ? C4 C18 C17 119.8(4) . . ? C20 C19 H19A 109.5 . . ? C20 C19 H19B 109.5 . . ? H19A C19 H19B 109.5 . . ? C20 C19 H19C 109.5 . . ? H19A C19 H19C 109.5 . . ? H19B C19 H19C 109.5 . . ? O2 C20 C21 125.3(5) . . ? O2 C20 C19 116.4(6) . . ? C21 C20 C19 118.3(5) . . ? C22 C21 C20 124.6(5) . . ? O1 C22 C21 125.6(5) . . ? O1 C22 C23 115.6(5) . . ? C21 C22 C23 118.8(5) . . ? C22 C23 H23A 109.5 . . ? C22 C23 H23B 109.5 . . ? H23A C23 H23B 109.5 . . ? C22 C23 H23C 109.5 . . ? H23A C23 H23C 109.5 . . ? H23B C23 H23C 109.5 . . ? C25 C24 H24A 109.5 . . ? C25 C24 H24B 109.5 . . ? H24A C24 H24B 109.5 . . ? C25 C24 H24C 109.5 . . ? H24A C24 H24C 109.5 . . ? H24B C24 H24C 109.5 . . ? O4 C25 C26 125.4(5) . . ? O4 C25 C24 116.1(5) . . ? C26 C25 C24 118.5(5) . . ? C25 C26 C27 124.7(5) . . ? C25 C26 H26 117.7 . . ? C27 C26 H26 117.6 . . ? O3 C27 C26 124.4(5) . . ? O3 C27 C28 116.6(5) . . ? C26 C27 C28 118.9(5) . . ? C27 C28 H28A 109.5 . . ? C27 C28 H28B 109.5 . . ? H28A C28 H28B 109.5 . . ? C27 C28 H28C 109.5 . . ? H28A C28 H28C 109.5 . . ? H28B C28 H28C 109.5 . . ? C30 C29 H29A 109.5 . . ? C30 C29 H29B 109.5 . . ? H29A C29 H29B 109.5 . . ? C30 C29 H29C 109.5 . . ? H29A C29 H29C 109.5 . . ? H29B C29 H29C 109.5 . . ? O5 C30 C31 125.9(5) . . ? O5 C30 C29 116.8(5) . . ? C31 C30 C29 117.3(5) . . ? C32 C31 C30 123.9(5) . . ? C32 C31 H31 118.0 . . ? C30 C31 H31 118.0 . . ? O6 C32 C31 125.8(5) . . ? O6 C32 C33 116.9(5) . . ? C31 C32 C33 117.3(5) . . ? C32 C33 H33A 109.5 . . ? C32 C33 H33B 109.5 . . ? H33A C33 H33B 109.5 . . ? C32 C33 H33C 109.5 . . ? H33A C33 H33C 109.5 . . ? H33B C33 H33C 109.5 . . ? O7 C34 H34A 109.5 . . ? O7 C34 H34B 109.5 . . ? H34A C34 H34B 109.5 . . ? O7 C34 H34C 109.5 . . ? H34A C34 H34C 109.5 . . ? H34B C34 H34C 109.5 . . ? _diffrn_measured_fraction_theta_max 0.976 _diffrn_reflns_theta_full 27.48 _diffrn_measured_fraction_theta_full 0.976 _refine_diff_density_max 0.756 _refine_diff_density_min -0.889 _refine_diff_density_rms 0.135