# Supplementary Material (ESI) for Chemical Communications # This journal is © The Royal Society of Chemistry 2010 data_global _journal_coden_Cambridge 182 _journal_volume ? _journal_page_first ? _journal_year ? loop_ _publ_author_name 'Zucchi, Gael' 'Ephritikhine, Michel' 'Thuery, Pierre' 'Riviere, Eric' _publ_contact_author_name 'Zucchi, Gael' _publ_contact_author_email gael.zucchi@cea.fr _publ_section_title ; Europium(II) Compounds: Simple Synthesis of a Molecular Complex in Water and Coordination Polymers with 2,2-Bipyrimidine Mediated Ferromagnetic Interactions ; # Attachment 'CIF-ZUCCHI.txt' data_1 _database_code_depnum_ccdc_archive 'CCDC 784445' #TrackingRef 'CIF-ZUCCHI.txt' _audit_creation_method SHELXL-97 _chemical_name_systematic ? _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C16 H22 Cl2 Eu N8 O5' _chemical_formula_weight 629.28 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' Cl Cl 0.1484 0.1585 '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/c' 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 8.8617(8) _cell_length_b 32.465(4) _cell_length_c 8.0104(9) _cell_angle_alpha 90.00 _cell_angle_beta 102.643(7) _cell_angle_gamma 90.00 _cell_volume 2248.7(4) _cell_formula_units_Z 4 _cell_measurement_temperature 100(2) _cell_measurement_reflns_used 69169 _cell_measurement_theta_min 2.36 _cell_measurement_theta_max 25.68 _exptl_crystal_description lath _exptl_crystal_colour 'dark brown' _exptl_crystal_size_max 0.08 _exptl_crystal_size_mid 0.04 _exptl_crystal_size_min 0.02 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.859 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1244 _exptl_absorpt_coefficient_mu 3.073 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.684 _exptl_absorpt_correction_T_max 0.940 _exptl_absorpt_process_details 'SCALEPACK (Otwinowski & Minor, 1997)' _exptl_special_details 'crystal-to-detector distance 30 mm' _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 'Nonius Kappa-CCD area-detector diffractometer' _diffrn_measurement_method 'two \f and four \w scans with 2\% steps' _diffrn_standards_interval_time 0 _diffrn_standards_number 0 _diffrn_standards_decay_% 0 _diffrn_reflns_number 69169 _diffrn_reflns_av_R_equivalents 0.0580 _diffrn_reflns_av_sigmaI/netI 0.0765 _diffrn_reflns_limit_h_min -10 _diffrn_reflns_limit_h_max 10 _diffrn_reflns_limit_k_min -39 _diffrn_reflns_limit_k_max 39 _diffrn_reflns_limit_l_min -9 _diffrn_reflns_limit_l_max 9 _diffrn_reflns_theta_min 2.36 _diffrn_reflns_theta_max 25.68 _reflns_number_total 4257 _reflns_number_gt 3161 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'COLLECT (Nonius, 1998)' _computing_cell_refinement 'HKL2000 (Otwinowski & Minor, 1997)' _computing_data_reduction 'HKL2000 (Otwinowski & Minor, 1997)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1997)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'SHELXTL (Sheldrick, 1999)' _computing_publication_material 'SHELXTL (Sheldrick, 1999); PLATON (Spek, 2003)' _refine_special_details ; Structure solved by direct methods and subsequent Fourier-difference synthesis. All non-hydrogen atoms were refined with anisotropic displacement parameters. The H atoms bound to O atoms were found on a Fourier-difference map and all the others were introduced at calculated positions. All were treated as riding atoms with an isotropic displacement parameter equal to 1.2 times that of the parent atom. 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^)+(0.0203P)^2^] 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 4257 _refine_ls_number_parameters 289 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0670 _refine_ls_R_factor_gt 0.0386 _refine_ls_wR_factor_ref 0.0666 _refine_ls_wR_factor_gt 0.0612 _refine_ls_goodness_of_fit_ref 0.997 _refine_ls_restrained_S_all 0.997 _refine_ls_shift/su_max 0.001 _refine_ls_shift/su_mean 0.000 _diffrn_measured_fraction_theta_max 0.999 _diffrn_reflns_theta_full 25.68 _diffrn_measured_fraction_theta_full 0.999 _refine_diff_density_max 0.562 _refine_diff_density_min -1.004 _refine_diff_density_rms 0.127 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 Eu Eu 0.19424(3) 0.377746(8) 0.14314(4) 0.01968(8) Uani 1 1 d . . . Cl1 Cl 0.25453(15) 0.40647(4) 0.51250(17) 0.0245(3) Uani 1 1 d . . . Cl2 Cl 0.67469(15) 0.33941(4) -0.04225(18) 0.0286(3) Uani 1 1 d . . . O1 O 0.4960(4) 0.37004(11) 0.2506(5) 0.0306(9) Uani 1 1 d . . . H1A H 0.5411 0.3594 0.3552 0.037 Uiso 1 1 d R . . H1B H 0.5517 0.3607 0.1945 0.037 Uiso 1 1 d R . . O2 O 0.3326(4) 0.37245(10) -0.1047(4) 0.0265(9) Uani 1 1 d . . . H2A H 0.2763 0.3820 -0.2093 0.032 Uiso 1 1 d R . . H2B H 0.4206 0.3712 -0.1149 0.032 Uiso 1 1 d R . . O3 O 0.0164(4) 0.33658(10) -0.1012(4) 0.0241(8) Uani 1 1 d . . . H3A H -0.0910 0.3341 -0.1143 0.029 Uiso 1 1 d R . . H3B H 0.0639 0.3195 -0.1744 0.029 Uiso 1 1 d R . . O4 O -0.0758(4) 0.40659(10) 0.1614(5) 0.0264(9) Uani 1 1 d . . . H4A H -0.1562 0.3961 0.0952 0.032 Uiso 1 1 d R . . H4B H -0.1001 0.4337 0.1792 0.032 Uiso 1 1 d R . . O5 O 0.6036(4) 0.38211(12) 0.5930(5) 0.0351(10) Uani 1 1 d . . . H5A H 0.6147 0.3697 0.6945 0.042 Uiso 1 1 d R . . H5B H 0.5118 0.3953 0.5788 0.042 Uiso 1 1 d R . . N1 N 0.3138(5) 0.45779(13) 0.1408(6) 0.0222(10) Uani 1 1 d . . . N2 N 0.0759(5) 0.43526(13) -0.1239(6) 0.0248(11) Uani 1 1 d . . . N3 N 0.0493(5) 0.50567(12) -0.2120(6) 0.0229(10) Uani 1 1 d . . . N4 N 0.3063(5) 0.52541(13) 0.0194(6) 0.0260(11) Uani 1 1 d . . . N5 N 0.0381(5) 0.32190(12) 0.3151(6) 0.0222(10) Uani 1 1 d . . . N6 N 0.2647(5) 0.29249(12) 0.1699(5) 0.0234(10) Uani 1 1 d . . . N7 N 0.1794(5) 0.22394(12) 0.2049(6) 0.0234(10) Uani 1 1 d . . . N8 N -0.0601(5) 0.25353(12) 0.3239(6) 0.0235(10) Uani 1 1 d . . . C1 C 0.2551(6) 0.48695(15) 0.0261(7) 0.0217(12) Uani 1 1 d . . . C2 C 0.1176(6) 0.47514(15) -0.1135(7) 0.0201(12) Uani 1 1 d . . . C3 C -0.0431(6) 0.42577(16) -0.2504(7) 0.0265(13) Uani 1 1 d . . . H3 H -0.0749 0.3984 -0.2643 0.032 Uiso 1 1 calc R . . C4 C -0.1214(6) 0.45505(16) -0.3623(7) 0.0269(13) Uani 1 1 d . . . H4 H -0.2039 0.4479 -0.4508 0.032 Uiso 1 1 calc R . . C5 C -0.0719(6) 0.49521(17) -0.3370(7) 0.0250(13) Uani 1 1 d . . . H5 H -0.1238 0.5156 -0.4085 0.030 Uiso 1 1 calc R . . C6 C 0.4301(6) 0.53526(16) 0.1433(7) 0.0279(13) Uani 1 1 d . . . H6 H 0.4702 0.5618 0.1445 0.033 Uiso 1 1 calc R . . C7 C 0.4997(6) 0.50818(16) 0.2675(7) 0.0255(13) Uani 1 1 d . . . H7 H 0.5849 0.5158 0.3520 0.031 Uiso 1 1 calc R . . C8 C 0.4374(6) 0.46898(16) 0.2615(7) 0.0255(13) Uani 1 1 d . . . H8 H 0.4826 0.4498 0.3435 0.031 Uiso 1 1 calc R . . C9 C 0.0380(6) 0.28127(15) 0.2868(7) 0.0210(12) Uani 1 1 d . . . C10 C 0.1688(6) 0.26488(15) 0.2140(7) 0.0203(12) Uani 1 1 d . . . C11 C 0.3858(6) 0.27718(16) 0.1150(7) 0.0261(13) Uani 1 1 d . . . H11 H 0.4571 0.2953 0.0856 0.031 Uiso 1 1 calc R . . C12 C 0.4077(6) 0.23516(16) 0.1008(7) 0.0260(13) Uani 1 1 d . . . H12 H 0.4919 0.2247 0.0625 0.031 Uiso 1 1 calc R . . C13 C 0.2993(6) 0.20948(16) 0.1460(7) 0.0268(13) Uani 1 1 d . . . H13 H 0.3098 0.1812 0.1351 0.032 Uiso 1 1 calc R . . C14 C -0.1672(6) 0.26845(16) 0.4048(7) 0.0272(13) Uani 1 1 d . . . H14 H -0.2401 0.2504 0.4314 0.033 Uiso 1 1 calc R . . C15 C -0.1727(6) 0.30917(16) 0.4494(7) 0.0260(13) Uani 1 1 d . . . H15 H -0.2439 0.3187 0.5102 0.031 Uiso 1 1 calc R . . C16 C -0.0674(6) 0.33522(16) 0.3997(6) 0.0232(12) Uani 1 1 d . . . H16 H -0.0697 0.3631 0.4260 0.028 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 Eu 0.02097(13) 0.01630(12) 0.02265(14) 0.00031(14) 0.00665(10) -0.00022(13) Cl1 0.0261(7) 0.0228(7) 0.0249(8) 0.0009(6) 0.0064(6) 0.0009(5) Cl2 0.0232(7) 0.0302(8) 0.0339(9) 0.0000(6) 0.0095(6) 0.0006(6) O1 0.0273(19) 0.038(2) 0.026(2) 0.0001(17) 0.0053(17) 0.0068(16) O2 0.0222(19) 0.035(2) 0.023(2) 0.0023(18) 0.0079(17) 0.0038(17) O3 0.0225(19) 0.024(2) 0.026(2) -0.0043(17) 0.0051(17) -0.0001(16) O4 0.025(2) 0.021(2) 0.033(2) 0.0012(17) 0.0054(18) 0.0038(16) O5 0.031(2) 0.046(3) 0.028(2) 0.003(2) 0.0049(18) 0.006(2) N1 0.018(2) 0.026(2) 0.023(3) 0.001(2) 0.006(2) 0.001(2) N2 0.021(2) 0.026(3) 0.028(3) -0.001(2) 0.009(2) -0.001(2) N3 0.028(2) 0.020(2) 0.022(3) 0.001(2) 0.009(2) 0.003(2) N4 0.033(3) 0.018(2) 0.028(3) -0.001(2) 0.009(2) -0.002(2) N5 0.022(2) 0.020(2) 0.024(3) 0.003(2) 0.005(2) 0.0033(19) N6 0.031(2) 0.020(2) 0.020(3) 0.003(2) 0.007(2) -0.003(2) N7 0.027(2) 0.016(2) 0.028(3) 0.001(2) 0.006(2) 0.0012(19) N8 0.023(2) 0.018(2) 0.031(3) 0.005(2) 0.009(2) -0.0023(19) C1 0.021(3) 0.023(3) 0.025(3) 0.001(2) 0.013(3) 0.004(2) C2 0.022(3) 0.021(3) 0.020(3) -0.005(2) 0.011(2) 0.002(2) C3 0.022(3) 0.019(3) 0.040(4) -0.002(3) 0.011(3) 0.000(2) C4 0.028(3) 0.026(3) 0.027(3) 0.001(3) 0.007(3) 0.005(2) C5 0.028(3) 0.032(3) 0.018(3) 0.001(3) 0.011(3) 0.007(3) C6 0.032(3) 0.022(3) 0.033(4) -0.007(3) 0.015(3) -0.006(3) C7 0.028(3) 0.025(3) 0.024(3) -0.003(3) 0.007(3) -0.004(2) C8 0.028(3) 0.022(3) 0.028(3) 0.002(3) 0.010(3) 0.002(2) C9 0.024(3) 0.020(3) 0.017(3) 0.006(2) 0.000(2) 0.003(2) C10 0.025(3) 0.019(3) 0.016(3) 0.002(2) 0.003(2) 0.000(2) C11 0.025(3) 0.027(3) 0.028(3) 0.002(3) 0.009(3) -0.001(2) C12 0.029(3) 0.025(3) 0.024(3) 0.004(3) 0.008(3) 0.008(3) C13 0.036(3) 0.018(3) 0.024(3) 0.004(3) 0.003(3) 0.007(3) C14 0.025(3) 0.027(3) 0.029(4) 0.007(2) 0.004(3) -0.004(2) C15 0.024(3) 0.027(3) 0.030(3) 0.000(3) 0.012(3) 0.004(2) C16 0.031(3) 0.018(3) 0.020(3) -0.001(2) 0.003(3) 0.004(2) _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 O2 2.558(3) . ? Eu O3 2.598(3) . ? Eu O4 2.604(3) . ? Eu O1 2.635(3) . ? Eu N1 2.808(4) . ? Eu N5 2.816(4) . ? Eu N6 2.835(4) . ? Eu N2 2.860(4) . ? Eu Cl1 3.0360(14) . ? O1 H1A 0.9142 . ? O1 H1B 0.7969 . ? O2 H2A 0.9290 . ? O2 H2B 0.8025 . ? O3 H3A 0.9380 . ? O3 H3B 0.9672 . ? O4 H4A 0.8601 . ? O4 H4B 0.9234 . ? O5 H5A 0.8933 . ? O5 H5B 0.9044 . ? N1 C1 1.343(6) . ? N1 C8 1.343(7) . ? N2 C3 1.329(7) . ? N2 C2 1.344(6) . ? N3 C2 1.327(6) . ? N3 C5 1.342(7) . ? N4 C1 1.333(6) . ? N4 C6 1.347(7) . ? N5 C9 1.338(6) . ? N5 C16 1.341(6) . ? N6 C10 1.335(6) . ? N6 C11 1.341(6) . ? N7 C10 1.336(6) . ? N7 C13 1.338(6) . ? N8 C9 1.329(6) . ? N8 C14 1.351(6) . ? C1 C2 1.512(7) . ? C3 C4 1.384(7) . ? C3 H3 0.9300 . ? C4 C5 1.376(7) . ? C4 H4 0.9300 . ? C5 H5 0.9300 . ? C6 C7 1.369(7) . ? C6 H6 0.9300 . ? C7 C8 1.384(7) . ? C7 H7 0.9300 . ? C8 H8 0.9300 . ? C9 C10 1.504(7) . ? C11 C12 1.386(7) . ? C11 H11 0.9300 . ? C12 C13 1.379(7) . ? C12 H12 0.9300 . ? C13 H13 0.9300 . ? C14 C15 1.373(7) . ? C14 H14 0.9300 . ? C15 C16 1.381(7) . ? C15 H15 0.9300 . ? C16 H16 0.9300 . ? 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 O2 Eu O3 72.26(10) . . ? O2 Eu O4 132.12(11) . . ? O3 Eu O4 79.28(11) . . ? O2 Eu O1 67.82(11) . . ? O3 Eu O1 127.00(11) . . ? O4 Eu O1 153.52(11) . . ? O2 Eu N1 79.13(11) . . ? O3 Eu N1 129.68(12) . . ? O4 Eu N1 91.16(11) . . ? O1 Eu N1 74.50(11) . . ? O2 Eu N5 134.96(11) . . ? O3 Eu N5 75.84(12) . . ? O4 Eu N5 69.39(11) . . ? O1 Eu N5 110.55(11) . . ? N1 Eu N5 145.63(12) . . ? O2 Eu N6 81.84(11) . . ? O3 Eu N6 69.03(12) . . ? O4 Eu N6 122.47(11) . . ? O1 Eu N6 72.04(12) . . ? N1 Eu N6 145.78(12) . . ? N5 Eu N6 57.20(11) . . ? O2 Eu N2 67.84(11) . . ? O3 Eu N2 73.12(12) . . ? O4 Eu N2 67.44(11) . . ? O1 Eu N2 119.07(11) . . ? N1 Eu N2 57.86(12) . . ? N5 Eu N2 130.32(12) . . ? N6 Eu N2 137.10(12) . . ? O2 Eu Cl1 139.92(8) . . ? O3 Eu Cl1 147.20(7) . . ? O4 Eu Cl1 78.61(8) . . ? O1 Eu Cl1 76.19(8) . . ? N1 Eu Cl1 74.69(9) . . ? N5 Eu Cl1 73.84(9) . . ? N6 Eu Cl1 103.73(9) . . ? N2 Eu Cl1 119.07(9) . . ? Eu O1 H1A 123.0 . . ? Eu O1 H1B 124.2 . . ? H1A O1 H1B 99.9 . . ? Eu O2 H2A 115.0 . . ? Eu O2 H2B 136.4 . . ? H2A O2 H2B 105.5 . . ? Eu O3 H3A 124.2 . . ? Eu O3 H3B 118.6 . . ? H3A O3 H3B 116.7 . . ? Eu O4 H4A 118.1 . . ? Eu O4 H4B 126.8 . . ? H4A O4 H4B 106.4 . . ? H5A O5 H5B 104.2 . . ? C1 N1 C8 115.7(5) . . ? C1 N1 Eu 124.6(3) . . ? C8 N1 Eu 119.7(3) . . ? C3 N2 C2 115.6(5) . . ? C3 N2 Eu 121.3(3) . . ? C2 N2 Eu 122.1(4) . . ? C2 N3 C5 116.1(5) . . ? C1 N4 C6 115.0(5) . . ? C9 N5 C16 115.4(4) . . ? C9 N5 Eu 122.3(3) . . ? C16 N5 Eu 120.7(3) . . ? C10 N6 C11 116.1(4) . . ? C10 N6 Eu 122.2(3) . . ? C11 N6 Eu 121.0(3) . . ? C10 N7 C13 116.1(4) . . ? C9 N8 C14 115.2(4) . . ? N4 C1 N1 127.1(5) . . ? N4 C1 C2 115.7(5) . . ? N1 C1 C2 117.1(4) . . ? N3 C2 N2 126.8(5) . . ? N3 C2 C1 116.0(4) . . ? N2 C2 C1 117.1(5) . . ? N2 C3 C4 122.4(5) . . ? N2 C3 H3 118.8 . . ? C4 C3 H3 118.8 . . ? C5 C4 C3 117.2(5) . . ? C5 C4 H4 121.4 . . ? C3 C4 H4 121.4 . . ? N3 C5 C4 121.8(5) . . ? N3 C5 H5 119.1 . . ? C4 C5 H5 119.1 . . ? N4 C6 C7 123.2(5) . . ? N4 C6 H6 118.4 . . ? C7 C6 H6 118.4 . . ? C6 C7 C8 116.9(5) . . ? C6 C7 H7 121.6 . . ? C8 C7 H7 121.6 . . ? N1 C8 C7 122.0(5) . . ? N1 C8 H8 119.0 . . ? C7 C8 H8 119.0 . . ? N8 C9 N5 127.3(5) . . ? N8 C9 C10 116.4(4) . . ? N5 C9 C10 116.2(4) . . ? N6 C10 N7 126.7(4) . . ? N6 C10 C9 117.0(4) . . ? N7 C10 C9 116.3(4) . . ? N6 C11 C12 121.9(5) . . ? N6 C11 H11 119.1 . . ? C12 C11 H11 119.1 . . ? C13 C12 C11 117.1(5) . . ? C13 C12 H12 121.5 . . ? C11 C12 H12 121.5 . . ? N7 C13 C12 122.2(5) . . ? N7 C13 H13 118.9 . . ? C12 C13 H13 118.9 . . ? N8 C14 C15 122.6(5) . . ? N8 C14 H14 118.7 . . ? C15 C14 H14 118.7 . . ? C14 C15 C16 116.7(5) . . ? C14 C15 H15 121.6 . . ? C16 C15 H15 121.6 . . ? N5 C16 C15 122.6(5) . . ? N5 C16 H16 118.7 . . ? C15 C16 H16 118.7 . . ? loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA _geom_hbond_site_symmetry_A O1 H1A O5 0.91 2.00 2.728(5) 134.9 . O1 H1B Cl2 0.80 2.48 3.260(3) 165.1 . O2 H2A Cl1 0.93 2.33 3.189(4) 152.9 1_554 O2 H2B Cl2 0.80 2.43 3.150(3) 150.2 . O3 H3A Cl2 0.94 2.28 3.167(3) 157.4 1_455 O3 H3B N7 0.97 2.10 3.056(5) 170.0 4_565 O4 H4A Cl2 0.86 2.47 3.275(4) 155.3 1_455 O4 H4B N3 0.92 2.02 2.879(5) 153.3 3_565 O5 H5A Cl2 0.89 2.28 3.170(4) 173.0 1_556 O5 H5B Cl1 0.90 2.25 3.120(4) 160.3 . #===END data_2 _database_code_depnum_ccdc_archive 'CCDC 784446' #TrackingRef 'CIF-ZUCCHI.txt' _audit_creation_method SHELXL-97 _chemical_name_systematic ? _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C8.50 H8 Cl2 Eu N4 O0.50' _chemical_formula_weight 397.05 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' 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' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting orthorhombic _symmetry_space_group_name_H-M 'P 21 21 21' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, -y, z+1/2' '-x, y+1/2, -z+1/2' 'x+1/2, -y+1/2, -z' _cell_length_a 9.7048(4) _cell_length_b 13.1460(3) _cell_length_c 17.5916(6) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 2244.32(13) _cell_formula_units_Z 8 _cell_measurement_temperature 100(2) _cell_measurement_reflns_used 32795 _cell_measurement_theta_min 3.13 _cell_measurement_theta_max 25.68 _exptl_crystal_description platelet _exptl_crystal_colour 'translucent dark brown' _exptl_crystal_size_max 0.17 _exptl_crystal_size_mid 0.12 _exptl_crystal_size_min 0.06 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 2.350 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1504 _exptl_absorpt_coefficient_mu 6.043 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.555 _exptl_absorpt_correction_T_max 0.696 _exptl_absorpt_process_details 'SCALEPACK (Otwinowski & Minor, 1997)' _exptl_special_details 'crystal-to-detector distance 30 mm' _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 'Nonius Kappa-CCD area-detector diffractometer' _diffrn_measurement_method 'two \f scans with 2\% steps' _diffrn_standards_interval_time 0 _diffrn_standards_number 0 _diffrn_standards_decay_% 0 _diffrn_reflns_number 32795 _diffrn_reflns_av_R_equivalents 0.0523 _diffrn_reflns_av_sigmaI/netI 0.0254 _diffrn_reflns_limit_h_min -11 _diffrn_reflns_limit_h_max 11 _diffrn_reflns_limit_k_min -15 _diffrn_reflns_limit_k_max 15 _diffrn_reflns_limit_l_min -21 _diffrn_reflns_limit_l_max 21 _diffrn_reflns_theta_min 3.13 _diffrn_reflns_theta_max 25.68 _reflns_number_total 4205 _reflns_number_gt 3906 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'COLLECT (Hooft, 1998)' _computing_cell_refinement 'HKL2000 (Otwinowski & Minor, 1997)' _computing_data_reduction 'HKL2000 (Otwinowski & Minor, 1997)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1997)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'SHELXTL (Sheldrick, 1999)' _computing_publication_material 'SHELXTL (Sheldrick, 1999); PLATON (Spek, 2003)' _refine_special_details ; Structure solved by direct methods and subsequent Fourier-difference synthesis. ADDSYM (PLATON) indicates a 96% fit for space group Pnma. However, firstly, a significant number of observed reflections do not follow the reflection conditions for this group and, secondly, refinement of the model proved extremely unstable and did not give a R1 factor lower than 6%. For these reasons, it was deemed preferable to retain the chiral space group P212121 and to consider the structure as pseudo-centrosymmetric only. All non-hydrogen atoms were refined with anisotropic displacement parameters. The H atom bound to O1 was found on a Fourier-difference map and all the others were introduced at calculated positions. All were treated as riding atoms with an isotropic displacement parameter equal to 1.2 (OH, CH) or 1.5 (CH~3~) times that of the parent atom. 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^)+(0.0246P)^2^+5.2573P] 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 0.48(2) _refine_ls_number_reflns 4205 _refine_ls_number_parameters 291 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0262 _refine_ls_R_factor_gt 0.0231 _refine_ls_wR_factor_ref 0.0566 _refine_ls_wR_factor_gt 0.0550 _refine_ls_goodness_of_fit_ref 1.046 _refine_ls_restrained_S_all 1.046 _refine_ls_shift/su_max 0.001 _refine_ls_shift/su_mean 0.000 _diffrn_measured_fraction_theta_max 0.986 _diffrn_reflns_theta_full 25.68 _diffrn_measured_fraction_theta_full 0.986 _refine_diff_density_max 1.703 _refine_diff_density_min -0.681 _refine_diff_density_rms 0.109 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 0.86020(4) 0.02116(2) 0.121497(12) 0.01212(8) Uani 1 1 d . . . Eu2 Eu 0.64186(4) -0.02258(2) -0.115903(12) 0.01192(8) Uani 1 1 d . . . Cl1 Cl 1.01057(10) 0.10331(8) 0.25221(9) 0.0154(2) Uani 1 1 d . . . Cl2 Cl 0.68156(11) -0.02736(8) 0.25275(8) 0.0189(2) Uani 1 1 d . . . Cl3 Cl 0.91289(16) -0.02821(13) -0.04055(7) 0.0162(3) Uani 1 1 d . . . Cl4 Cl 0.58737(16) 0.02746(13) 0.04680(7) 0.0157(3) Uani 1 1 d . . . N1 N 1.0545(7) 0.1599(4) 0.0702(3) 0.0143(13) Uani 1 1 d . . . N2 N 0.8096(7) 0.2288(4) 0.1228(3) 0.0149(15) Uani 1 1 d . . . N3 N 0.9058(6) 0.3954(4) 0.1339(3) 0.0177(14) Uani 1 1 d . . . N4 N 1.1601(8) 0.3175(4) 0.0995(3) 0.0160(13) Uani 1 1 d . . . N5 N 1.0965(6) -0.1051(4) 0.1376(3) 0.0132(12) Uani 1 1 d . . . N6 N 0.8437(8) -0.1833(4) 0.1053(3) 0.0144(12) Uani 1 1 d . . . N7 N 0.9535(7) -0.3379(4) 0.0658(3) 0.0150(14) Uani 1 1 d . . . N8 N 1.1934(7) -0.2719(4) 0.1225(3) 0.0143(14) Uani 1 1 d . . . C1 C 1.0515(10) 0.2549(6) 0.0963(4) 0.0164(17) Uani 1 1 d . . . C2 C 0.9164(9) 0.2948(5) 0.1194(3) 0.0154(17) Uani 1 1 d . . . C3 C 0.6876(8) 0.2665(5) 0.1390(4) 0.0171(17) Uani 1 1 d . . . H3 H 0.6126 0.2225 0.1410 0.020 Uiso 1 1 calc R . . C4 C 0.6662(8) 0.3678(5) 0.1532(3) 0.0162(15) Uani 1 1 d . . . H4 H 0.5785 0.3929 0.1634 0.019 Uiso 1 1 calc R . . C5 C 0.7801(7) 0.4317(5) 0.1519(3) 0.0162(14) Uani 1 1 d . . . H5 H 0.7696 0.5003 0.1635 0.019 Uiso 1 1 calc R . . C6 C 1.2805(8) 0.2784(6) 0.0785(4) 0.0180(16) Uani 1 1 d . . . H6 H 1.3587 0.3189 0.0829 0.022 Uiso 1 1 calc R . . C7 C 1.2953(8) 0.1823(5) 0.0508(3) 0.0168(16) Uani 1 1 d . . . H7 H 1.3806 0.1569 0.0360 0.020 Uiso 1 1 calc R . . C8 C 1.1762(7) 0.1245(5) 0.0457(3) 0.0155(16) Uani 1 1 d . . . H8 H 1.1808 0.0596 0.0249 0.019 Uiso 1 1 calc R . . C9 C 1.0904(8) -0.2039(5) 0.1210(3) 0.0104(15) Uani 1 1 d . . . C10 C 0.9526(9) -0.2448(5) 0.0961(4) 0.0116(15) Uani 1 1 d . . . C11 C 0.7210(8) -0.2212(6) 0.0840(4) 0.0175(17) Uani 1 1 d . . . H11 H 0.6420 -0.1821 0.0906 0.021 Uiso 1 1 calc R . . C12 C 0.7098(9) -0.3193(5) 0.0518(3) 0.0172(16) Uani 1 1 d . . . H12 H 0.6252 -0.3464 0.0373 0.021 Uiso 1 1 calc R . . C13 C 0.8316(8) -0.3729(5) 0.0429(3) 0.0183(17) Uani 1 1 d . . . H13 H 0.8281 -0.4364 0.0197 0.022 Uiso 1 1 calc R . . C14 C 1.3197(8) -0.2336(5) 0.1413(4) 0.0178(17) Uani 1 1 d . . . H14 H 1.3953 -0.2771 0.1421 0.021 Uiso 1 1 calc R . . C15 C 1.3388(9) -0.1310(5) 0.1593(3) 0.0178(15) Uani 1 1 d . . . H15 H 1.4251 -0.1051 0.1716 0.021 Uiso 1 1 calc R . . C16 C 1.2230(7) -0.0702(5) 0.1579(3) 0.0168(14) Uani 1 1 d . . . H16 H 1.2319 -0.0022 0.1716 0.020 Uiso 1 1 calc R . . O1 O 0.4232(6) 0.1082(4) 0.3006(3) 0.0460(13) Uani 1 1 d . . . H1 H 0.4934 0.0679 0.2870 0.055 Uiso 1 1 d R . . C17 C 0.3876(6) 0.1663(5) 0.2400(5) 0.0374(16) Uani 1 1 d . . . H17A H 0.2892 0.1734 0.2382 0.056 Uiso 1 1 calc R . . H17B H 0.4193 0.1344 0.1941 0.056 Uiso 1 1 calc R . . H17C H 0.4291 0.2323 0.2447 0.056 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 Eu1 0.01196(18) 0.01096(15) 0.01346(13) -0.00078(10) -0.00014(12) -0.0001(2) Eu2 0.01122(17) 0.01099(15) 0.01356(13) -0.00081(10) -0.00034(12) 0.0004(2) Cl1 0.0148(5) 0.0173(5) 0.0142(5) 0.0011(7) 0.0010(7) -0.0021(4) Cl2 0.0151(5) 0.0263(6) 0.0154(5) 0.0004(8) 0.0000(6) -0.0036(4) Cl3 0.0142(8) 0.0180(7) 0.0164(6) -0.0024(6) -0.0008(5) 0.0005(8) Cl4 0.0132(8) 0.0181(7) 0.0157(6) -0.0003(6) -0.0012(5) 0.0018(8) N1 0.013(4) 0.015(3) 0.015(3) -0.001(2) 0.004(2) 0.000(3) N2 0.022(4) 0.010(3) 0.013(3) 0.003(2) 0.002(2) -0.002(3) N3 0.023(4) 0.017(3) 0.012(2) 0.000(2) 0.003(2) 0.004(3) N4 0.015(3) 0.014(3) 0.019(2) 0.001(2) 0.000(3) -0.001(3) N5 0.011(3) 0.011(3) 0.017(2) -0.003(2) 0.004(2) 0.002(2) N6 0.011(3) 0.019(3) 0.014(2) 0.0014(19) -0.003(3) -0.001(3) N7 0.019(4) 0.014(3) 0.011(3) -0.002(2) 0.003(2) -0.003(3) N8 0.009(4) 0.015(3) 0.019(3) -0.002(2) 0.002(2) 0.000(2) C1 0.019(5) 0.016(4) 0.014(3) 0.000(3) -0.002(3) 0.003(4) C2 0.024(5) 0.008(3) 0.014(3) -0.001(2) -0.002(3) 0.001(3) C3 0.017(5) 0.019(4) 0.016(3) 0.001(2) 0.004(3) -0.009(3) C4 0.014(4) 0.021(3) 0.013(3) 0.003(2) 0.004(2) 0.002(3) C5 0.020(4) 0.015(3) 0.014(3) 0.000(2) 0.001(3) 0.002(3) C6 0.005(4) 0.026(4) 0.023(3) 0.001(3) -0.003(3) 0.001(3) C7 0.012(4) 0.023(4) 0.016(3) 0.002(3) 0.003(3) -0.002(3) C8 0.019(5) 0.015(3) 0.012(3) 0.003(2) 0.003(2) 0.005(3) C9 0.007(4) 0.016(4) 0.009(3) 0.001(2) 0.000(2) -0.001(3) C10 0.013(4) 0.014(3) 0.008(3) -0.001(3) 0.000(3) 0.000(3) C11 0.020(5) 0.013(4) 0.020(3) 0.001(3) -0.004(3) 0.002(3) C12 0.016(4) 0.015(4) 0.020(3) 0.007(3) -0.002(3) -0.006(3) C13 0.024(5) 0.014(3) 0.017(3) -0.002(2) -0.002(3) 0.001(3) C14 0.011(4) 0.019(4) 0.023(3) 0.005(3) 0.003(3) -0.005(3) C15 0.014(4) 0.021(3) 0.019(3) 0.000(2) 0.001(3) -0.005(3) C16 0.019(4) 0.015(3) 0.016(3) 0.002(2) -0.003(3) -0.005(3) O1 0.040(3) 0.044(3) 0.054(3) 0.008(2) 0.001(3) 0.003(2) C17 0.022(3) 0.036(3) 0.055(5) -0.001(4) -0.006(4) -0.002(2) _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 N6 2.708(5) . ? Eu1 N2 2.774(6) . ? Eu1 N1 2.775(6) . ? Eu1 N5 2.844(5) . ? Eu1 Cl1 2.9297(15) . ? Eu1 Cl2 2.9570(13) . ? Eu1 Cl4 2.9571(15) . ? Eu1 Cl3 2.9680(13) . ? Eu2 N4 2.717(5) 4_455 ? Eu2 N7 2.735(6) 4_445 ? Eu2 N8 2.750(6) 4_445 ? Eu2 N3 2.854(6) 4_455 ? Eu2 Cl3 2.9463(15) . ? Eu2 Cl1 2.9492(15) 2_654 ? Eu2 Cl2 2.9507(13) 2_654 ? Eu2 Cl4 2.9841(13) . ? Cl1 Eu2 2.9492(15) 2_655 ? Cl2 Eu2 2.9506(13) 2_655 ? N1 C1 1.331(9) . ? N1 C8 1.341(9) . ? N2 C3 1.315(11) . ? N2 C2 1.353(10) . ? N3 C5 1.347(9) . ? N3 C2 1.350(9) . ? N3 Eu2 2.854(6) 4 ? N4 C6 1.329(10) . ? N4 C1 1.339(10) . ? N4 Eu2 2.717(5) 4 ? N5 C9 1.332(9) . ? N5 C16 1.359(8) . ? N6 C10 1.341(10) . ? N6 C11 1.344(10) . ? N7 C13 1.332(10) . ? N7 C10 1.334(9) . ? N7 Eu2 2.735(6) 4_545 ? N8 C9 1.342(9) . ? N8 C14 1.366(10) . ? N8 Eu2 2.750(6) 4_545 ? C1 C2 1.470(13) . ? C3 C4 1.371(9) . ? C4 C5 1.388(10) . ? C6 C7 1.362(10) . ? C7 C8 1.386(10) . ? C9 C10 1.506(11) . ? C11 C12 1.413(10) . ? C12 C13 1.385(11) . ? C14 C15 1.397(9) . ? C15 C16 1.379(10) . ? O1 C17 1.356(8) . ? 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 N6 Eu1 N2 165.32(19) . . ? N6 Eu1 N1 131.21(19) . . ? N2 Eu1 N1 58.39(18) . . ? N6 Eu1 N5 58.60(19) . . ? N2 Eu1 N5 135.73(19) . . ? N1 Eu1 N5 82.42(16) . . ? N6 Eu1 Cl1 118.54(12) . . ? N2 Eu1 Cl1 73.69(12) . . ? N1 Eu1 Cl1 71.00(11) . . ? N5 Eu1 Cl1 74.67(11) . . ? N6 Eu1 Cl2 80.40(12) . . ? N2 Eu1 Cl2 95.86(12) . . ? N1 Eu1 Cl2 142.59(11) . . ? N5 Eu1 Cl2 105.62(10) . . ? Cl1 Eu1 Cl2 76.04(4) . . ? N6 Eu1 Cl4 85.88(15) . . ? N2 Eu1 Cl4 79.48(14) . . ? N1 Eu1 Cl4 116.45(13) . . ? N5 Eu1 Cl4 141.47(11) . . ? Cl1 Eu1 Cl4 141.67(4) . . ? Cl2 Eu1 Cl4 80.10(4) . . ? N6 Eu1 Cl3 72.08(11) . . ? N2 Eu1 Cl3 104.68(11) . . ? N1 Eu1 Cl3 73.39(11) . . ? N5 Eu1 Cl3 80.15(11) . . ? Cl1 Eu1 Cl3 138.47(4) . . ? Cl2 Eu1 Cl3 143.50(4) . . ? Cl4 Eu1 Cl3 74.55(3) . . ? N4 Eu2 N7 132.44(19) 4_455 4_445 ? N4 Eu2 N8 165.32(19) 4_455 4_445 ? N7 Eu2 N8 58.43(18) 4_445 4_445 ? N4 Eu2 N3 58.85(19) 4_455 4_455 ? N7 Eu2 N3 83.81(17) 4_445 4_455 ? N8 Eu2 N3 135.80(18) 4_445 4_455 ? N4 Eu2 Cl3 85.35(15) 4_455 . ? N7 Eu2 Cl3 115.79(13) 4_445 . ? N8 Eu2 Cl3 80.32(13) 4_445 . ? N3 Eu2 Cl3 141.38(12) 4_455 . ? N4 Eu2 Cl1 118.24(13) 4_455 2_654 ? N7 Eu2 Cl1 71.14(11) 4_445 2_654 ? N8 Eu2 Cl1 72.81(12) 4_445 2_654 ? N3 Eu2 Cl1 73.78(11) 4_455 2_654 ? Cl3 Eu2 Cl1 142.44(4) . 2_654 ? N4 Eu2 Cl2 79.88(13) 4_455 2_654 ? N7 Eu2 Cl2 142.13(11) 4_445 2_654 ? N8 Eu2 Cl2 94.57(12) 4_445 2_654 ? N3 Eu2 Cl2 104.41(11) 4_455 2_654 ? Cl3 Eu2 Cl2 80.76(4) . 2_654 ? Cl1 Eu2 Cl2 75.84(3) 2_654 2_654 ? N4 Eu2 Cl4 72.01(11) 4_455 . ? N7 Eu2 Cl4 73.78(11) 4_445 . ? N8 Eu2 Cl4 106.82(11) 4_445 . ? N3 Eu2 Cl4 80.51(11) 4_455 . ? Cl3 Eu2 Cl4 74.47(3) . . ? Cl1 Eu2 Cl4 138.16(4) 2_654 . ? Cl2 Eu2 Cl4 143.61(4) 2_654 . ? Eu1 Cl1 Eu2 103.59(3) . 2_655 ? Eu2 Cl2 Eu1 102.88(3) 2_655 . ? Eu2 Cl3 Eu1 105.83(5) . . ? Eu1 Cl4 Eu2 105.15(5) . . ? C1 N1 C8 117.1(7) . . ? C1 N1 Eu1 119.3(5) . . ? C8 N1 Eu1 118.3(4) . . ? C3 N2 C2 117.3(6) . . ? C3 N2 Eu1 122.1(5) . . ? C2 N2 Eu1 119.7(5) . . ? C5 N3 C2 117.4(7) . . ? C5 N3 Eu2 123.0(4) . 4 ? C2 N3 Eu2 119.4(5) . 4 ? C6 N4 C1 116.3(6) . . ? C6 N4 Eu2 118.1(5) . 4 ? C1 N4 Eu2 124.3(5) . 4 ? C9 N5 C16 115.2(6) . . ? C9 N5 Eu1 120.8(5) . . ? C16 N5 Eu1 123.9(4) . . ? C10 N6 C11 116.2(6) . . ? C10 N6 Eu1 124.4(5) . . ? C11 N6 Eu1 116.7(5) . . ? C13 N7 C10 115.6(7) . . ? C13 N7 Eu2 117.4(4) . 4_545 ? C10 N7 Eu2 119.4(5) . 4_545 ? C9 N8 C14 115.3(6) . . ? C9 N8 Eu2 121.2(5) . 4_545 ? C14 N8 Eu2 122.4(5) . 4_545 ? N1 C1 N4 125.0(8) . . ? N1 C1 C2 116.7(8) . . ? N4 C1 C2 118.1(6) . . ? N3 C2 N2 124.1(8) . . ? N3 C2 C1 118.0(7) . . ? N2 C2 C1 117.8(6) . . ? N2 C3 C4 122.8(7) . . ? C3 C4 C5 117.6(7) . . ? N3 C5 C4 120.7(6) . . ? N4 C6 C7 123.5(7) . . ? C6 C7 C8 116.3(7) . . ? N1 C8 C7 121.6(6) . . ? N5 C9 N8 127.8(7) . . ? N5 C9 C10 116.8(6) . . ? N8 C9 C10 115.4(6) . . ? N7 C10 N6 127.3(8) . . ? N7 C10 C9 116.0(7) . . ? N6 C10 C9 116.7(6) . . ? N6 C11 C12 121.3(7) . . ? C13 C12 C11 116.3(7) . . ? N7 C13 C12 123.3(6) . . ? N8 C14 C15 122.0(7) . . ? C16 C15 C14 116.5(7) . . ? N5 C16 C15 123.1(6) . . ? loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA _geom_hbond_site_symmetry_A O1 H1 Cl2 0.90 2.29 3.189(5) 176.7 . #===END data_3 _database_code_depnum_ccdc_archive 'CCDC 784447' #TrackingRef 'CIF-ZUCCHI.txt' _audit_creation_method SHELXL-97 _chemical_name_systematic ? _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C20 H21 Eu I2 N10 O3' _chemical_formula_weight 855.23 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' I I -0.4742 1.8119 '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 'C 2/c' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y, -z+1/2' 'x+1/2, y+1/2, z' '-x+1/2, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y, z-1/2' '-x+1/2, -y+1/2, -z' 'x+1/2, -y+1/2, z-1/2' _cell_length_a 31.7279(17) _cell_length_b 10.1284(6) _cell_length_c 20.2074(14) _cell_angle_alpha 90.00 _cell_angle_beta 123.588(4) _cell_angle_gamma 90.00 _cell_volume 5409.5(6) _cell_formula_units_Z 8 _cell_measurement_temperature 100(2) _cell_measurement_reflns_used 80299 _cell_measurement_theta_min 3.01 _cell_measurement_theta_max 25.68 _exptl_crystal_description parallelepiped _exptl_crystal_colour 'dark brown' _exptl_crystal_size_max 0.17 _exptl_crystal_size_mid 0.15 _exptl_crystal_size_min 0.08 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 2.100 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 3232 _exptl_absorpt_coefficient_mu 4.643 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.344 _exptl_absorpt_correction_T_max 0.690 _exptl_absorpt_process_details 'SCALEPACK (Otwinowski & Minor, 1997)' _exptl_special_details 'crystal-to-detector distance 30 mm' _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 'Nonius Kappa-CCD area-detector diffractometer' _diffrn_measurement_method 'two \f and three \w scans with 2\% steps (310 frames)' _diffrn_standards_interval_time 0 _diffrn_standards_number 0 _diffrn_standards_decay_% 0 _diffrn_reflns_number 80299 _diffrn_reflns_av_R_equivalents 0.0359 _diffrn_reflns_av_sigmaI/netI 0.0467 _diffrn_reflns_limit_h_min -38 _diffrn_reflns_limit_h_max 38 _diffrn_reflns_limit_k_min -12 _diffrn_reflns_limit_k_max 12 _diffrn_reflns_limit_l_min -24 _diffrn_reflns_limit_l_max 24 _diffrn_reflns_theta_min 3.01 _diffrn_reflns_theta_max 25.68 _reflns_number_total 5142 _reflns_number_gt 4099 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'COLLECT (Nonius, 1998)' _computing_cell_refinement 'HKL2000 (Otwinowski & Minor, 1997)' _computing_data_reduction 'HKL2000 (Otwinowski & Minor, 1997)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1997)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'SHELXTL (Sheldrick, 1999)' _computing_publication_material 'SHELXTL (Sheldrick, 1999); PLATON (Spek, 2003)' _refine_special_details ; Structure solved by direct methods and subsequent Fourier-difference synthesis. All non-hydrogen atoms were refined with anisotropic displacement parameters. Restraints on bond lengths and angles (rings treated as idealized hexagons) and displacement parameters were applied for the very badly resolved free bipyrimidine molecule, which is disordered over a binary axis and has been affected with a 0.5 occupancy factor. The H atoms bound to O atoms were found on a Fourier-difference map and all the others were introduced at calculated positions. All were treated as riding atoms with an isotropic displacement parameter equal to 1.2 times that of the parent atom. The highest residual electron density peak is located near the free bipyrimidine molecule. 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^)+(0.0668P)^2^+51.0210P] 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 5142 _refine_ls_number_parameters 355 _refine_ls_number_restraints 72 _refine_ls_R_factor_all 0.0588 _refine_ls_R_factor_gt 0.0431 _refine_ls_wR_factor_ref 0.1186 _refine_ls_wR_factor_gt 0.1109 _refine_ls_goodness_of_fit_ref 1.014 _refine_ls_restrained_S_all 1.011 _refine_ls_shift/su_max 0.001 _refine_ls_shift/su_mean 0.000 _diffrn_measured_fraction_theta_max 0.997 _diffrn_reflns_theta_full 25.68 _diffrn_measured_fraction_theta_full 0.997 _refine_diff_density_max 2.722 _refine_diff_density_min -1.509 _refine_diff_density_rms 0.220 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 Eu Eu 0.835482(13) 0.07500(4) 0.37078(2) 0.02323(12) Uani 1 1 d . . . I1 I 0.81532(2) 0.47437(6) 0.50500(4) 0.04005(17) Uani 1 1 d . . . I2 I 0.893691(18) 0.47188(5) 0.29171(3) 0.03011(15) Uani 1 1 d . . . O1 O 0.8309(2) 0.1188(6) 0.4933(3) 0.0325(12) Uani 1 1 d . . . H1A H 0.8329 0.2045 0.5109 0.039 Uiso 1 1 d R . . H1B H 0.8478 0.0727 0.5399 0.039 Uiso 1 1 d R . . O2 O 0.83699(19) 0.3297(5) 0.3743(3) 0.0304(12) Uani 1 1 d . . . H2A H 0.8309 0.3657 0.4127 0.037 Uiso 1 1 d R . . H2B H 0.8445 0.3956 0.3529 0.037 Uiso 1 1 d R . . O3 O 0.89765(19) 0.1184(5) 0.3264(3) 0.0301(12) Uani 1 1 d . . . H3A H 0.9272 0.0803 0.3476 0.036 Uiso 1 1 d R . . H3B H 0.9075 0.1971 0.3247 0.036 Uiso 1 1 d R . . N1 N 0.7403(2) 0.1887(6) 0.3104(4) 0.0262(14) Uani 1 1 d . . . N2 N 0.7784(2) 0.1869(6) 0.2182(4) 0.0272(14) Uani 1 1 d . . . N3 N 0.7247(2) 0.3677(6) 0.1431(4) 0.0271(14) Uani 1 1 d . . . N4 N 0.6851(2) 0.3661(6) 0.2310(4) 0.0271(14) Uani 1 1 d . . . N5 N 0.9316(2) 0.1356(7) 0.5024(4) 0.0346(16) Uani 1 1 d . . . N6 N 0.9042(2) -0.1230(6) 0.4681(4) 0.0287(14) Uani 1 1 d . . . N7 N 0.9882(2) -0.1848(6) 0.5725(4) 0.0332(16) Uani 1 1 d . . . N8 N 1.0167(2) 0.0702(6) 0.5995(4) 0.0281(14) Uani 1 1 d . . . C1 C 0.7218(3) 0.2773(8) 0.2515(4) 0.0262(16) Uani 1 1 d . . . C2 C 0.7432(3) 0.2780(7) 0.2016(4) 0.0245(15) Uani 1 1 d . . . C3 C 0.7424(3) 0.3608(8) 0.0961(4) 0.0275(16) Uani 1 1 d . . . H3 H 0.7297 0.4195 0.0539 0.033 Uiso 1 1 calc R . . C4 C 0.7780(3) 0.2719(8) 0.1075(5) 0.0293(17) Uani 1 1 d . . . H4 H 0.7901 0.2699 0.0748 0.035 Uiso 1 1 calc R . . C5 C 0.7953(3) 0.1846(8) 0.1703(5) 0.0294(17) Uani 1 1 d . . . H5 H 0.8195 0.1222 0.1795 0.035 Uiso 1 1 calc R . . C6 C 0.7182(3) 0.1871(8) 0.3510(5) 0.0297(17) Uani 1 1 d . . . H6 H 0.7294 0.1260 0.3918 0.036 Uiso 1 1 calc R . . C7 C 0.6793(3) 0.2730(7) 0.3348(4) 0.0253(15) Uani 1 1 d . . . H7 H 0.6646 0.2712 0.3639 0.030 Uiso 1 1 calc R . . C8 C 0.6640(3) 0.3598(8) 0.2742(5) 0.0289(17) Uani 1 1 d . . . H8 H 0.6378 0.4178 0.2615 0.035 Uiso 1 1 calc R . . C9 C 0.9676(3) 0.0447(7) 0.5439(4) 0.0244(16) Uani 1 1 d . . . C10 C 0.9524(3) -0.0967(8) 0.5272(5) 0.0275(17) Uani 1 1 d . . . C11 C 0.9748(3) -0.3110(8) 0.5592(6) 0.041(2) Uani 1 1 d . . . H11 H 0.9989 -0.3750 0.5899 0.049 Uiso 1 1 calc R . . C12 C 0.9259(3) -0.3509(8) 0.5010(5) 0.036(2) Uani 1 1 d . . . H12 H 0.9166 -0.4394 0.4927 0.044 Uiso 1 1 calc R . . C13 C 0.8917(3) -0.2516(8) 0.4559(5) 0.0326(18) Uani 1 1 d . . . H13 H 0.8588 -0.2750 0.4157 0.039 Uiso 1 1 calc R . . C14 C 0.9461(3) 0.2582(8) 0.5215(6) 0.045(2) Uani 1 1 d . . . H14 H 0.9218 0.3238 0.4949 0.054 Uiso 1 1 calc R . . C15 C 0.9949(3) 0.2972(9) 0.5784(5) 0.042(2) Uani 1 1 d . . . H15 H 1.0039 0.3855 0.5908 0.051 Uiso 1 1 calc R . . C16 C 1.0293(3) 0.1962(8) 0.6156(5) 0.0319(18) Uani 1 1 d . . . H16 H 1.0628 0.2174 0.6537 0.038 Uiso 1 1 calc R . . N9 N 0.9037(3) -0.0201(5) 0.6363(4) 0.055(2) Uani 0.50 1 d PGU . . C22 C 0.8889(3) -0.1518(6) 0.6224(4) 0.062(3) Uani 0.50 1 d PGU . . H22A H 0.8551 -0.1749 0.5800 0.074 Uiso 0.50 1 d PR . . C23 C 0.9230(3) -0.2500(5) 0.6698(5) 0.055(2) Uani 0.50 1 d PGU . . H23A H 0.9128 -0.3409 0.6602 0.065 Uiso 0.50 1 d PR . . C24 C 0.9720(3) -0.2166(6) 0.7311(5) 0.069(3) Uani 0.50 1 d PGU . . H24A H 0.9955 -0.2844 0.7639 0.083 Uiso 0.50 1 d PR . . N12 N 0.9868(2) -0.0849(7) 0.7451(5) 0.064(3) Uani 0.50 1 d PGU . . C17 C 0.9526(3) 0.0133(5) 0.6977(5) 0.058(2) Uani 0.50 1 d PGU . . N11 N 1.0233(3) 0.1855(6) 0.7718(8) 0.050(3) Uani 0.50 1 d PGU . . C19 C 1.0381(3) 0.3170(7) 0.7821(6) 0.060(3) Uani 0.50 1 d PGU . . H19A H 1.0731 0.3401 0.8180 0.073 Uiso 0.50 1 d PR . . C20 C 1.0023(3) 0.4152(5) 0.7402(7) 0.056(3) Uani 0.50 1 d PGU . . H20A H 1.0125 0.5061 0.7473 0.067 Uiso 0.50 1 d PR . . C21 C 0.9517(3) 0.3818(6) 0.6881(6) 0.064(3) Uani 0.50 1 d PGU . . H21A H 0.9269 0.4496 0.6592 0.076 Uiso 0.50 1 d PR . . N10 N 0.9369(3) 0.2503(7) 0.6779(6) 0.046(2) Uani 0.50 1 d PGU . . C18 C 0.9727(4) 0.1521(5) 0.7197(8) 0.050(2) Uani 0.50 1 d PGU . . 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 0.0217(2) 0.0188(2) 0.0260(2) -0.00077(15) 0.01121(16) 0.00008(15) I1 0.0576(4) 0.0287(3) 0.0485(4) -0.0037(2) 0.0386(3) -0.0016(3) I2 0.0278(3) 0.0258(3) 0.0328(3) 0.0014(2) 0.0144(2) -0.0030(2) O1 0.041(3) 0.032(3) 0.025(3) 0.000(2) 0.018(2) 0.006(3) O2 0.035(3) 0.023(3) 0.035(3) 0.001(2) 0.020(2) -0.002(2) O3 0.025(3) 0.021(3) 0.041(3) 0.004(2) 0.017(2) 0.001(2) N1 0.022(3) 0.024(3) 0.029(3) 0.005(3) 0.013(3) 0.005(3) N2 0.021(3) 0.030(4) 0.028(3) -0.001(3) 0.012(3) 0.001(3) N3 0.027(3) 0.026(3) 0.027(3) -0.001(3) 0.014(3) -0.002(3) N4 0.023(3) 0.022(3) 0.034(3) 0.001(3) 0.014(3) 0.000(3) N5 0.029(3) 0.020(3) 0.045(4) 0.001(3) 0.015(3) 0.001(3) N6 0.025(3) 0.019(3) 0.035(4) 0.001(3) 0.013(3) -0.002(3) N7 0.025(3) 0.019(3) 0.042(4) 0.003(3) 0.010(3) 0.006(3) N8 0.022(3) 0.023(3) 0.034(4) -0.002(3) 0.012(3) -0.001(3) C1 0.022(3) 0.025(4) 0.029(4) 0.001(3) 0.013(3) 0.002(3) C2 0.024(4) 0.023(4) 0.023(4) -0.002(3) 0.012(3) -0.003(3) C3 0.031(4) 0.024(4) 0.023(4) 0.003(3) 0.012(3) -0.004(3) C4 0.029(4) 0.029(4) 0.032(4) -0.003(3) 0.019(3) -0.006(3) C5 0.025(4) 0.029(4) 0.033(4) -0.003(3) 0.016(3) 0.000(3) C6 0.026(4) 0.032(4) 0.028(4) 0.003(3) 0.012(3) -0.005(3) C7 0.024(4) 0.024(4) 0.029(4) 0.002(3) 0.016(3) -0.001(3) C8 0.024(4) 0.030(4) 0.034(4) -0.003(3) 0.017(3) -0.002(3) C9 0.020(3) 0.024(4) 0.029(4) -0.003(3) 0.013(3) -0.003(3) C10 0.024(4) 0.028(4) 0.031(4) -0.001(3) 0.015(3) -0.002(3) C11 0.028(4) 0.024(5) 0.052(5) 0.005(4) 0.010(4) 0.005(3) C12 0.029(4) 0.020(4) 0.044(5) 0.002(3) 0.009(4) 0.004(3) C13 0.026(4) 0.023(4) 0.041(5) -0.002(3) 0.013(4) 0.000(3) C14 0.027(4) 0.021(4) 0.055(6) -0.002(4) 0.003(4) 0.000(3) C15 0.039(5) 0.027(5) 0.049(5) -0.004(4) 0.017(4) -0.005(4) C16 0.031(4) 0.027(4) 0.033(4) -0.004(3) 0.015(3) -0.004(3) N9 0.079(4) 0.035(3) 0.034(3) 0.010(3) 0.021(3) -0.004(3) C22 0.078(5) 0.050(4) 0.050(4) 0.011(4) 0.031(4) 0.011(4) C23 0.081(5) 0.046(4) 0.047(4) 0.021(4) 0.042(4) 0.023(4) C24 0.080(5) 0.052(4) 0.059(4) 0.016(4) 0.028(4) 0.012(4) N12 0.073(4) 0.045(4) 0.056(4) 0.012(4) 0.024(4) 0.018(3) C17 0.070(4) 0.045(4) 0.054(4) 0.010(3) 0.032(3) 0.011(3) N11 0.049(4) 0.043(4) 0.064(5) 0.007(4) 0.036(4) 0.020(4) C19 0.060(4) 0.047(5) 0.068(5) 0.012(4) 0.031(4) 0.022(4) C20 0.055(4) 0.051(4) 0.066(5) 0.003(4) 0.036(4) 0.023(4) C21 0.065(4) 0.049(5) 0.066(5) 0.014(4) 0.030(4) 0.017(4) N10 0.052(4) 0.042(4) 0.057(4) 0.010(4) 0.037(3) 0.018(4) C18 0.055(4) 0.039(4) 0.060(4) 0.016(4) 0.035(3) 0.017(3) _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 O2 2.580(6) . ? Eu O1 2.599(5) . ? Eu O3 2.616(5) . ? Eu N3 2.746(6) 4_645 ? Eu N4 2.766(6) 4_645 ? Eu N5 2.788(7) . ? Eu N1 2.803(6) . ? Eu N2 2.809(6) . ? Eu N6 2.811(6) . ? O1 H1A 0.9267 . ? O1 H1B 0.9123 . ? O2 H2A 0.9699 . ? O2 H2B 0.8961 . ? O3 H3A 0.8752 . ? O3 H3B 0.8634 . ? N1 C1 1.339(10) . ? N1 C6 1.342(10) . ? N2 C2 1.340(9) . ? N2 C5 1.343(10) . ? N3 C2 1.342(9) . ? N3 C3 1.346(10) . ? N3 Eu 2.746(6) 4_655 ? N4 C1 1.344(9) . ? N4 C8 1.362(10) . ? N4 Eu 2.766(6) 4_655 ? N5 C14 1.306(11) . ? N5 C9 1.341(10) . ? N6 C13 1.344(10) . ? N6 C10 1.348(10) . ? N7 C11 1.328(11) . ? N7 C10 1.333(10) . ? N8 C16 1.323(10) . ? N8 C9 1.348(9) . ? C1 C2 1.495(10) . ? C3 C4 1.360(11) . ? C3 H3 0.9300 . ? C4 C5 1.387(11) . ? C4 H4 0.9300 . ? C5 H5 0.9300 . ? C6 C7 1.393(11) . ? C6 H6 0.9300 . ? C7 C8 1.361(11) . ? C7 H7 0.9300 . ? C8 H8 0.9300 . ? C9 C10 1.489(10) . ? C11 C12 1.391(11) . ? C11 H11 0.9300 . ? C12 C13 1.386(11) . ? C12 H12 0.9300 . ? C13 H13 0.9300 . ? C14 C15 1.381(12) . ? C14 H14 0.9300 . ? C15 C16 1.377(12) . ? C15 H15 0.9300 . ? C16 H16 0.9300 . ? N9 C22 1.3900 . ? N9 C17 1.3900 . ? C22 C23 1.3900 . ? C22 H22A 0.9603 . ? C23 C24 1.3900 . ? C23 H23A 0.9599 . ? C24 N12 1.3900 . ? C24 H24A 0.9597 . ? N12 C17 1.3900 . ? C17 C18 1.505(2) . ? N11 C19 1.3900 . ? N11 C18 1.3900 . ? C19 C20 1.3900 . ? C19 H19A 0.9599 . ? C20 C21 1.3900 . ? C20 H20A 0.9600 . ? C21 N10 1.3900 . ? C21 H21A 0.9603 . ? N10 C18 1.3900 . ? 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 O2 Eu O1 79.22(18) . . ? O2 Eu O3 80.53(16) . . ? O1 Eu O3 138.47(17) . . ? O2 Eu N3 140.20(17) . 4_645 ? O1 Eu N3 79.91(18) . 4_645 ? O3 Eu N3 135.01(17) . 4_645 ? O2 Eu N4 141.12(18) . 4_645 ? O1 Eu N4 136.47(19) . 4_645 ? O3 Eu N4 77.63(17) . 4_645 ? N3 Eu N4 58.33(18) 4_645 4_645 ? O2 Eu N5 76.10(18) . . ? O1 Eu N5 70.22(19) . . ? O3 Eu N5 69.89(19) . . ? N3 Eu N5 126.67(19) 4_645 . ? N4 Eu N5 124.15(19) 4_645 . ? O2 Eu N1 66.45(17) . . ? O1 Eu N1 74.31(17) . . ? O3 Eu N1 128.08(17) . . ? N3 Eu N1 75.44(18) 4_645 . ? N4 Eu N1 103.68(18) 4_645 . ? N5 Eu N1 132.14(19) . . ? O2 Eu N2 67.52(17) . . ? O1 Eu N2 129.43(18) . . ? O3 Eu N2 72.93(17) . . ? N3 Eu N2 101.95(18) 4_645 . ? N4 Eu N2 75.46(18) 4_645 . ? N5 Eu N2 131.21(19) . . ? N1 Eu N2 58.09(18) . . ? O2 Eu N6 134.33(17) . . ? O1 Eu N6 83.43(18) . . ? O3 Eu N6 85.41(17) . . ? N3 Eu N6 75.64(18) 4_645 . ? N4 Eu N6 75.35(18) 4_645 . ? N5 Eu N6 58.27(19) . . ? N1 Eu N6 146.04(18) . . ? N2 Eu N6 146.67(19) . . ? Eu O1 H1A 119.8 . . ? Eu O1 H1B 125.7 . . ? H1A O1 H1B 102.0 . . ? Eu O2 H2A 112.9 . . ? Eu O2 H2B 137.5 . . ? H2A O2 H2B 109.3 . . ? Eu O3 H3A 124.3 . . ? Eu O3 H3B 121.8 . . ? H3A O3 H3B 96.6 . . ? C1 N1 C6 115.6(6) . . ? C1 N1 Eu 119.9(5) . . ? C6 N1 Eu 122.0(5) . . ? C2 N2 C5 116.2(7) . . ? C2 N2 Eu 119.6(5) . . ? C5 N2 Eu 120.8(5) . . ? C2 N3 C3 115.8(6) . . ? C2 N3 Eu 123.3(5) . 4_655 ? C3 N3 Eu 120.4(5) . 4_655 ? C1 N4 C8 115.0(7) . . ? C1 N4 Eu 123.2(5) . 4_655 ? C8 N4 Eu 121.0(5) . 4_655 ? C14 N5 C9 115.4(7) . . ? C14 N5 Eu 120.8(5) . . ? C9 N5 Eu 123.4(5) . . ? C13 N6 C10 115.4(7) . . ? C13 N6 Eu 121.8(5) . . ? C10 N6 Eu 122.6(5) . . ? C11 N7 C10 116.7(7) . . ? C16 N8 C9 116.3(7) . . ? N1 C1 N4 126.9(7) . . ? N1 C1 C2 117.6(6) . . ? N4 C1 C2 115.5(7) . . ? N2 C2 N3 125.8(7) . . ? N2 C2 C1 117.0(6) . . ? N3 C2 C1 117.2(6) . . ? N3 C3 C4 123.2(7) . . ? N3 C3 H3 118.4 . . ? C4 C3 H3 118.4 . . ? C3 C4 C5 116.6(7) . . ? C3 C4 H4 121.7 . . ? C5 C4 H4 121.7 . . ? N2 C5 C4 122.3(7) . . ? N2 C5 H5 118.9 . . ? C4 C5 H5 118.9 . . ? N1 C6 C7 122.9(7) . . ? N1 C6 H6 118.5 . . ? C7 C6 H6 118.5 . . ? C8 C7 C6 116.3(7) . . ? C8 C7 H7 121.8 . . ? C6 C7 H7 121.8 . . ? N4 C8 C7 123.3(7) . . ? N4 C8 H8 118.3 . . ? C7 C8 H8 118.3 . . ? N5 C9 N8 125.6(7) . . ? N5 C9 C10 117.4(6) . . ? N8 C9 C10 116.9(6) . . ? N7 C10 N6 126.5(7) . . ? N7 C10 C9 116.2(6) . . ? N6 C10 C9 117.3(7) . . ? N7 C11 C12 122.3(7) . . ? N7 C11 H11 118.8 . . ? C12 C11 H11 118.8 . . ? C13 C12 C11 116.5(7) . . ? C13 C12 H12 121.8 . . ? C11 C12 H12 121.8 . . ? N6 C13 C12 122.5(7) . . ? N6 C13 H13 118.7 . . ? C12 C13 H13 118.7 . . ? N5 C14 C15 124.6(8) . . ? N5 C14 H14 117.7 . . ? C15 C14 H14 117.7 . . ? C16 C15 C14 115.3(8) . . ? C16 C15 H15 122.4 . . ? C14 C15 H15 122.4 . . ? N8 C16 C15 122.8(7) . . ? N8 C16 H16 118.6 . . ? C15 C16 H16 118.6 . . ? C22 N9 C17 120.0 . . ? C23 C22 N9 120.0 . . ? C23 C22 H22A 120.0 . . ? N9 C22 H22A 120.0 . . ? C22 C23 C24 120.0 . . ? C22 C23 H23A 120.0 . . ? C24 C23 H23A 120.0 . . ? N12 C24 C23 120.0 . . ? N12 C24 H24A 120.0 . . ? C23 C24 H24A 120.0 . . ? C17 N12 C24 120.0 . . ? N12 C17 N9 120.0 . . ? N12 C17 C18 115.1(6) . . ? N9 C17 C18 124.9(6) . . ? C19 N11 C18 120.0 . . ? C20 C19 N11 120.0 . . ? C20 C19 H19A 120.0 . . ? N11 C19 H19A 120.0 . . ? C19 C20 C21 120.0 . . ? C19 C20 H20A 120.0 . . ? C21 C20 H20A 120.0 . . ? N10 C21 C20 120.0 . . ? N10 C21 H21A 120.0 . . ? C20 C21 H21A 120.0 . . ? C21 N10 C18 120.0 . . ? N10 C18 N11 120.0 . . ? N10 C18 C17 114.7(7) . . ? N11 C18 C17 125.0(7) . . ? loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA _geom_hbond_site_symmetry_A O1 H1A I1 0.93 2.78 3.660(6) 159.2 . O1 H1B N9 0.91 2.00 2.878(8) 160.7 . O2 H2A I1 0.97 2.44 3.407(5) 175.2 . O2 H2B I2 0.90 2.59 3.379(5) 147.5 . O3 H3A N8 0.88 2.13 2.962(8) 159.0 5_756 O3 H3B I2 0.86 2.84 3.637(5) 154.4 . #===END data_4 _database_code_depnum_ccdc_archive 'CCDC 784448' #TrackingRef 'CIF-ZUCCHI.txt' _audit_creation_method SHELXL-97 _chemical_name_systematic ? _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C11 H18 Eu I2 N4 O3' _chemical_formula_weight 660.05 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' I I -0.4742 1.8119 '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 8.7106(6) _cell_length_b 9.2393(7) _cell_length_c 11.6831(12) _cell_angle_alpha 93.001(4) _cell_angle_beta 93.467(6) _cell_angle_gamma 94.709(5) _cell_volume 933.81(14) _cell_formula_units_Z 2 _cell_measurement_temperature 100(2) _cell_measurement_reflns_used 29025 _cell_measurement_theta_min 3.02 _cell_measurement_theta_max 25.68 _exptl_crystal_description platelet _exptl_crystal_colour 'dark brown' _exptl_crystal_size_max 0.10 _exptl_crystal_size_mid 0.10 _exptl_crystal_size_min 0.03 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 2.347 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 610 _exptl_absorpt_coefficient_mu 6.677 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.574 _exptl_absorpt_correction_T_max 0.818 _exptl_absorpt_process_details 'SCALEPACK (Otwinowski & Minor, 1997)' _exptl_special_details 'crystal-to-detector distance 30 mm' _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 'Nonius Kappa-CCD area-detector diffractometer' _diffrn_measurement_method 'two \f and four \w scans with 2\% steps' _diffrn_standards_interval_time 0 _diffrn_standards_number 0 _diffrn_standards_decay_% 0 _diffrn_reflns_number 29025 _diffrn_reflns_av_R_equivalents 0.0618 _diffrn_reflns_av_sigmaI/netI 0.0805 _diffrn_reflns_limit_h_min -10 _diffrn_reflns_limit_h_max 10 _diffrn_reflns_limit_k_min -11 _diffrn_reflns_limit_k_max 11 _diffrn_reflns_limit_l_min -14 _diffrn_reflns_limit_l_max 14 _diffrn_reflns_theta_min 3.02 _diffrn_reflns_theta_max 25.68 _reflns_number_total 3526 _reflns_number_gt 2728 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'COLLECT (Nonius, 1998)' _computing_cell_refinement 'HKL2000 (Otwinowski & Minor, 1997)' _computing_data_reduction 'HKL2000 (Otwinowski & Minor, 1997)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1997)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'SHELXTL (Sheldrick, 1999)' _computing_publication_material 'SHELXTL (Sheldrick, 1999); PLATON (Spek, 2003)' _refine_special_details ; Structure solved by direct methods and subsequent Fourier-difference synthesis. All non-hydrogen atoms were refined with anisotropic displacement parameters. The H atoms bound to O atoms were found on a Fourier-difference map and all the others were introduced at calculated positions. All were treated as riding atoms with an isotropic displacement parameter equal to 1.2 (OH, CH) or 1.5 (CH~3~) times that of the parent atom. 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^)+(0.0635P)^2^] 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 3526 _refine_ls_number_parameters 193 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0667 _refine_ls_R_factor_gt 0.0479 _refine_ls_wR_factor_ref 0.1179 _refine_ls_wR_factor_gt 0.1114 _refine_ls_goodness_of_fit_ref 1.000 _refine_ls_restrained_S_all 1.000 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 _diffrn_measured_fraction_theta_max 0.994 _diffrn_reflns_theta_full 25.68 _diffrn_measured_fraction_theta_full 0.994 _refine_diff_density_max 1.702 _refine_diff_density_min -2.007 _refine_diff_density_rms 0.261 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 Eu Eu 0.18480(5) 0.14183(5) 0.76785(4) 0.02217(16) Uani 1 1 d . . . I1 I 0.29398(7) 0.29329(7) 1.02982(6) 0.02757(19) Uani 1 1 d . . . I2 I 0.73390(7) 0.30575(7) 0.53097(6) 0.02953(19) Uani 1 1 d . . . O1 O 0.0644(8) 0.3759(7) 0.7237(6) 0.0305(16) Uani 1 1 d . . . H1 H -0.0257 0.3586 0.6694 0.037 Uiso 1 1 d R . . O2 O 0.4328(8) 0.2928(7) 0.7183(6) 0.0316(16) Uani 1 1 d . . . H2 H 0.4877 0.2576 0.6649 0.038 Uiso 1 1 d R . . O3 O 0.3555(7) -0.0454(7) 0.6906(6) 0.0311(16) Uani 1 1 d . . . H3 H 0.3047 -0.1015 0.6285 0.037 Uiso 1 1 d R . . N1 N 0.1353(9) 0.1562(8) 0.5372(7) 0.0235(17) Uani 1 1 d . . . N2 N 0.0186(9) 0.0579(8) 0.3554(7) 0.0247(18) Uani 1 1 d . . . N3 N -0.0693(8) 0.1156(8) 0.8911(7) 0.0230(17) Uani 1 1 d . . . N4 N -0.1521(8) 0.0699(8) 1.0782(7) 0.0229(17) Uani 1 1 d . . . C1 C 0.0430(11) 0.0582(10) 0.4702(8) 0.024(2) Uani 1 1 d . . . C2 C 0.0957(10) 0.1644(10) 0.3046(8) 0.024(2) Uani 1 1 d . . . H2A H 0.0859 0.1652 0.2249 0.029 Uiso 1 1 calc R . . C3 C 0.1903(11) 0.2746(10) 0.3655(8) 0.024(2) Uani 1 1 d . . . H3A H 0.2398 0.3507 0.3291 0.029 Uiso 1 1 calc R . . C4 C 0.2065(10) 0.2648(10) 0.4824(8) 0.023(2) Uani 1 1 d . . . H4 H 0.2694 0.3364 0.5257 0.028 Uiso 1 1 calc R . . C5 C -0.0610(10) 0.0517(9) 0.9914(8) 0.023(2) Uani 1 1 d . . . C6 C -0.2637(12) 0.1655(10) 1.0633(9) 0.030(2) Uani 1 1 d . . . H6 H -0.3274 0.1839 1.1226 0.036 Uiso 1 1 calc R . . C7 C -0.2830(11) 0.2352(10) 0.9614(9) 0.027(2) Uani 1 1 d . . . H7 H -0.3595 0.2985 0.9502 0.032 Uiso 1 1 calc R . . C8 C -0.1810(11) 0.2048(10) 0.8762(9) 0.029(2) Uani 1 1 d . . . H8 H -0.1918 0.2486 0.8066 0.035 Uiso 1 1 calc R . . C9 C 0.0634(15) 0.5142(11) 0.7899(11) 0.045(3) Uani 1 1 d . . . H9A H -0.0407 0.5304 0.8064 0.068 Uiso 1 1 calc R . . H9B H 0.1052 0.5916 0.7464 0.068 Uiso 1 1 calc R . . H9C H 0.1250 0.5115 0.8607 0.068 Uiso 1 1 calc R . . C10 C 0.4676(13) 0.4453(11) 0.7511(10) 0.037(3) Uani 1 1 d . . . H10A H 0.4264 0.5025 0.6922 0.055 Uiso 1 1 calc R . . H10B H 0.5775 0.4669 0.7609 0.055 Uiso 1 1 calc R . . H10C H 0.4221 0.4681 0.8220 0.055 Uiso 1 1 calc R . . C11 C 0.5173(12) -0.0532(12) 0.7071(11) 0.044(3) Uani 1 1 d . . . H11A H 0.5650 -0.0324 0.6371 0.066 Uiso 1 1 calc R . . H11B H 0.5379 -0.1491 0.7281 0.066 Uiso 1 1 calc R . . H11C H 0.5585 0.0167 0.7671 0.066 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 Eu 0.0229(3) 0.0209(3) 0.0225(3) 0.00038(19) 0.00209(19) 0.00085(19) I1 0.0280(4) 0.0281(3) 0.0257(4) -0.0010(3) 0.0015(3) -0.0013(3) I2 0.0298(4) 0.0275(3) 0.0311(4) -0.0016(3) 0.0024(3) 0.0032(3) O1 0.029(4) 0.027(3) 0.035(4) 0.001(3) -0.003(3) 0.005(3) O2 0.030(4) 0.026(3) 0.039(5) 0.000(3) 0.011(3) -0.002(3) O3 0.028(4) 0.039(4) 0.026(4) -0.006(3) -0.001(3) 0.007(3) N1 0.023(4) 0.023(4) 0.024(5) 0.003(3) -0.001(3) 0.001(3) N2 0.022(4) 0.027(4) 0.025(5) -0.002(3) 0.005(3) 0.007(3) N3 0.019(4) 0.025(4) 0.026(5) 0.003(3) 0.003(3) 0.003(3) N4 0.019(4) 0.022(4) 0.027(5) 0.000(3) 0.002(3) 0.003(3) C1 0.029(5) 0.025(5) 0.017(5) -0.001(4) 0.003(4) 0.008(4) C2 0.024(5) 0.028(5) 0.021(5) 0.002(4) 0.001(4) 0.000(4) C3 0.025(5) 0.021(4) 0.027(6) 0.004(4) 0.004(4) 0.002(4) C4 0.018(5) 0.021(4) 0.031(6) -0.003(4) 0.004(4) 0.006(4) C5 0.022(5) 0.020(4) 0.026(5) -0.001(4) 0.000(4) -0.005(4) C6 0.034(6) 0.019(5) 0.034(6) -0.002(4) 0.006(5) -0.006(4) C7 0.025(5) 0.029(5) 0.029(6) 0.006(4) 0.001(4) 0.008(4) C8 0.037(6) 0.023(5) 0.026(6) 0.004(4) 0.001(4) 0.003(4) C9 0.059(8) 0.026(5) 0.050(8) -0.001(5) -0.012(6) 0.008(5) C10 0.046(7) 0.032(5) 0.031(6) -0.002(5) 0.007(5) -0.010(5) C11 0.027(6) 0.046(7) 0.060(9) 0.004(6) 0.004(5) 0.006(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 Eu O3 2.537(6) . ? Eu O1 2.543(6) . ? Eu O2 2.586(6) . ? Eu N3 2.714(7) . ? Eu N1 2.715(8) . ? Eu N4 2.735(8) 2_557 ? Eu N2 2.738(8) 2_556 ? Eu I1 3.3484(8) . ? O1 C9 1.459(12) . ? O1 H1 0.9759 . ? O2 C10 1.443(11) . ? O2 H2 0.8745 . ? O3 C11 1.419(12) . ? O3 H3 0.9357 . ? N1 C1 1.345(12) . ? N1 C4 1.347(12) . ? N2 C2 1.331(12) . ? N2 C1 1.344(12) . ? N2 Eu 2.738(8) 2_556 ? N3 C8 1.335(12) . ? N3 C5 1.340(12) . ? N4 C5 1.336(12) . ? N4 C6 1.375(12) . ? N4 Eu 2.735(8) 2_557 ? C1 C1 1.488(18) 2_556 ? C2 C3 1.392(13) . ? C2 H2A 0.9300 . ? C3 C4 1.372(13) . ? C3 H3A 0.9300 . ? C4 H4 0.9300 . ? C5 C5 1.499(18) 2_557 ? C6 C7 1.391(14) . ? C6 H6 0.9300 . ? C7 C8 1.407(14) . ? C7 H7 0.9300 . ? C8 H8 0.9300 . ? C9 H9A 0.9600 . ? C9 H9B 0.9600 . ? C9 H9C 0.9600 . ? C10 H10A 0.9600 . ? C10 H10B 0.9600 . ? C10 H10C 0.9600 . ? C11 H11A 0.9600 . ? C11 H11B 0.9600 . ? C11 H11C 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 O3 Eu O1 143.7(2) . . ? O3 Eu O2 75.5(2) . . ? O1 Eu O2 82.0(2) . . ? O3 Eu N3 131.8(2) . . ? O1 Eu N3 79.3(2) . . ? O2 Eu N3 149.3(2) . . ? O3 Eu N1 77.7(2) . . ? O1 Eu N1 70.2(2) . . ? O2 Eu N1 78.7(2) . . ? N3 Eu N1 116.7(2) . . ? O3 Eu N4 78.1(2) . 2_557 ? O1 Eu N4 137.5(2) . 2_557 ? O2 Eu N4 128.9(2) . 2_557 ? N3 Eu N4 59.5(2) . 2_557 ? N1 Eu N4 136.0(2) . 2_557 ? O3 Eu N2 76.3(2) . 2_556 ? O1 Eu N2 100.5(2) . 2_556 ? O2 Eu N2 133.4(2) . 2_556 ? N3 Eu N2 74.3(2) . 2_556 ? N1 Eu N2 59.5(2) . 2_556 ? N4 Eu N2 79.3(2) 2_557 2_556 ? O3 Eu I1 115.70(15) . . ? O1 Eu I1 87.86(16) . . ? O2 Eu I1 81.15(16) . . ? N3 Eu I1 74.06(17) . . ? N1 Eu I1 151.93(16) . . ? N4 Eu I1 72.11(16) 2_557 . ? N2 Eu I1 145.07(17) 2_556 . ? C9 O1 Eu 131.9(6) . . ? C9 O1 H1 111.5 . . ? Eu O1 H1 112.0 . . ? C10 O2 Eu 124.0(6) . . ? C10 O2 H2 115.7 . . ? Eu O2 H2 118.4 . . ? C11 O3 Eu 130.3(6) . . ? C11 O3 H3 116.8 . . ? Eu O3 H3 110.9 . . ? C1 N1 C4 115.6(8) . . ? C1 N1 Eu 123.9(6) . . ? C4 N1 Eu 120.4(6) . . ? C2 N2 C1 116.0(8) . . ? C2 N2 Eu 121.3(6) . 2_556 ? C1 N2 Eu 122.7(6) . 2_556 ? C8 N3 C5 116.5(8) . . ? C8 N3 Eu 120.3(6) . . ? C5 N3 Eu 119.2(6) . . ? C5 N4 C6 116.5(8) . . ? C5 N4 Eu 119.3(6) . 2_557 ? C6 N4 Eu 120.3(6) . 2_557 ? N2 C1 N1 126.2(8) . . ? N2 C1 C1 117.3(10) . 2_556 ? N1 C1 C1 116.4(10) . 2_556 ? N2 C2 C3 122.9(9) . . ? N2 C2 H2A 118.6 . . ? C3 C2 H2A 118.6 . . ? C4 C3 C2 116.3(9) . . ? C4 C3 H3A 121.8 . . ? C2 C3 H3A 121.8 . . ? N1 C4 C3 122.9(9) . . ? N1 C4 H4 118.5 . . ? C3 C4 H4 118.5 . . ? N4 C5 N3 126.5(9) . . ? N4 C5 C5 116.2(11) . 2_557 ? N3 C5 C5 117.3(10) . 2_557 ? N4 C6 C7 121.2(9) . . ? N4 C6 H6 119.4 . . ? C7 C6 H6 119.4 . . ? C6 C7 C8 116.5(9) . . ? C6 C7 H7 121.7 . . ? C8 C7 H7 121.7 . . ? N3 C8 C7 122.7(9) . . ? N3 C8 H8 118.7 . . ? C7 C8 H8 118.7 . . ? O1 C9 H9A 109.5 . . ? O1 C9 H9B 109.5 . . ? H9A C9 H9B 109.5 . . ? O1 C9 H9C 109.5 . . ? H9A C9 H9C 109.5 . . ? H9B C9 H9C 109.5 . . ? O2 C10 H10A 109.5 . . ? O2 C10 H10B 109.5 . . ? H10A C10 H10B 109.5 . . ? O2 C10 H10C 109.5 . . ? H10A C10 H10C 109.5 . . ? H10B C10 H10C 109.5 . . ? O3 C11 H11A 109.5 . . ? O3 C11 H11B 109.5 . . ? H11A C11 H11B 109.5 . . ? O3 C11 H11C 109.5 . . ? H11A C11 H11C 109.5 . . ? H11B C11 H11C 109.5 . . ? loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA _geom_hbond_site_symmetry_A O1 H1 I2 0.98 2.57 3.541(7) 178.0 1_455 O2 H2 I2 0.87 2.75 3.515(7) 146.7 . O3 H3 I2 0.94 2.57 3.448(7) 156.8 2_656