# Electronic Supplementary Material (ESI) for CrystEngComm # This journal is © The Royal Society of Chemistry 2012 ####################################################################### # # Cambridge Crystallographic Data Centre # CCDC # ####################################################################### # # This CIF contains data from an original supplementary publication # deposited with the CCDC, and may include chemical, crystal, # experimental, refinement, atomic coordinates, # anisotropic displacement parameters and molecular geometry data, # as required by the journal to which it was submitted. # # This CIF is provided on the understanding that it is used for bona # fide research purposes only. It may contain copyright material # of the CCDC or of third parties, and may not be copied or further # disseminated in any form, whether machine-readable or not, # except for the purpose of generating routine backup copies # on your local computer system. # # For further information on the CCDC, data deposition and # data retrieval see: # www.ccdc.cam.ac.uk # # Bona fide researchers may freely download Mercury and enCIFer # from this site to visualise CIF-encoded structures and # to carry out CIF format checking respectively. # ####################################################################### data_1 _database_code_depnum_ccdc_archive 'CCDC 865492' #TrackingRef '- 1.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C11 H11 N3 O9 Tb' _chemical_formula_weight 488.15 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' Tb Tb -0.1723 4.1537 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Monoclinic _symmetry_space_group_name_H-M P2(1)/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 8.3136(19) _cell_length_b 14.719(4) _cell_length_c 11.526(3) _cell_angle_alpha 90.00 _cell_angle_beta 90.807(5) _cell_angle_gamma 90.00 _cell_volume 1410.4(6) _cell_formula_units_Z 4 _cell_measurement_temperature 298(2) _cell_measurement_reflns_used 526 _cell_measurement_theta_min 2.245 _cell_measurement_theta_max 16.587 _exptl_crystal_description plan _exptl_crystal_colour colourless _exptl_crystal_size_max 0.10 _exptl_crystal_size_mid 0.04 _exptl_crystal_size_min 0.03 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 2.299 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 940 _exptl_absorpt_coefficient_mu 5.072 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.6310 _exptl_absorpt_correction_T_max 0.8627 _exptl_absorpt_process_details sadabs _exptl_special_details ; ? ; _diffrn_ambient_temperature 298(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'CCD area detector' _diffrn_measurement_method 'phi and omega scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 7316 _diffrn_reflns_av_R_equivalents 0.0919 _diffrn_reflns_av_sigmaI/netI 0.1155 _diffrn_reflns_limit_h_min -10 _diffrn_reflns_limit_h_max 6 _diffrn_reflns_limit_k_min -17 _diffrn_reflns_limit_k_max 17 _diffrn_reflns_limit_l_min -13 _diffrn_reflns_limit_l_max 13 _diffrn_reflns_theta_min 2.24 _diffrn_reflns_theta_max 25.50 _reflns_number_total 2611 _reflns_number_gt 1971 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SMART' _computing_data_reduction 'Bruker SAINT' _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^)+(0.0148P)^2^+3.2310P] 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 2611 _refine_ls_number_parameters 205 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0886 _refine_ls_R_factor_gt 0.0608 _refine_ls_wR_factor_ref 0.1172 _refine_ls_wR_factor_gt 0.1072 _refine_ls_goodness_of_fit_ref 1.056 _refine_ls_restrained_S_all 1.056 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group C1 C -0.2323(18) 0.3683(10) -0.2149(12) 0.045(4) Uani 1 1 d . . . H1 H -0.2282 0.4141 -0.2704 0.054 Uiso 1 1 calc R . . C2 C -0.1404(16) 0.3774(9) -0.1159(11) 0.041(4) Uani 1 1 d . . . H2 H -0.0731 0.4274 -0.1068 0.049 Uiso 1 1 calc R . . C3 C -0.1475(14) 0.3130(8) -0.0301(10) 0.021(3) Uani 1 1 d . . . C4 C -0.2446(15) 0.2357(8) -0.0536(11) 0.031(3) Uani 1 1 d . . . H4 H -0.2485 0.1879 -0.0009 0.038 Uiso 1 1 calc R . . C5 C -0.3334(16) 0.2324(9) -0.1558(12) 0.041(4) Uani 1 1 d . . . H5 H -0.4004 0.1828 -0.1693 0.049 Uiso 1 1 calc R . . C6 C -0.0567(16) 0.3192(8) 0.0808(10) 0.027(3) Uani 1 1 d . . . C7 C -0.0041(14) 0.3759(8) 0.2538(10) 0.023(3) Uani 1 1 d . . . C8 C 0.0730(14) 0.2944(7) 0.2394(10) 0.019(3) Uani 1 1 d . . . C9 C -0.0357(14) 0.4366(7) 0.3550(10) 0.0205(19) Uani 1 1 d . . . C10 C 0.1808(12) 0.2386(7) 0.3150(10) 0.015(3) Uani 1 1 d . . . C11 C 0.5270(15) -0.0028(7) 0.0643(9) 0.0205(19) Uani 1 1 d . . . Tb1 Tb 0.22247(7) 0.13243(3) 0.06694(4) 0.01470(18) Uani 1 1 d . . . N1 N 0.0384(11) 0.2593(6) 0.1293(8) 0.019(2) Uani 1 1 d . . . N2 N -0.0877(11) 0.3904(6) 0.1519(8) 0.022(2) Uani 1 1 d . . . H2A H -0.1484 0.4361 0.1360 0.026 Uiso 1 1 calc R . . N3 N -0.3266(13) 0.2973(8) -0.2354(9) 0.035(3) Uani 1 1 d . . . O1 O 0.2294(10) 0.1658(5) 0.2685(6) 0.024(2) Uani 1 1 d . . . O2 O 0.2199(9) 0.2626(5) 0.4146(7) 0.0229(19) Uani 1 1 d . . . O3 O 0.0090(10) 0.4106(5) 0.4533(7) 0.030(2) Uani 1 1 d . . . O4 O -0.1128(11) 0.5073(5) 0.3317(7) 0.035(2) Uani 1 1 d . . . O5 O 0.4427(10) 0.2334(5) 0.0957(7) 0.034(2) Uani 1 1 d . . . H5A H 0.4189 0.2894 0.0895 0.051 Uiso 1 1 d R . . H5B H 0.5131 0.2194 0.1469 0.051 Uiso 1 1 d R . . O6 O 0.6462(10) -0.0524(5) 0.0876(6) 0.0292(15) Uani 1 1 d . . . O7 O 0.4459(10) 0.0420(5) 0.1359(6) 0.0292(15) Uani 1 1 d . . . O8 O 0.6895(10) 0.5263(5) 0.0856(7) 0.037(2) Uani 1 1 d . . . H8A H 0.7243 0.5661 0.1330 0.056 Uiso 1 1 d R . . H8B H 0.6730 0.5438 0.0162 0.056 Uiso 1 1 d R . . O9 O 0.4163(12) 0.4239(6) 0.1444(8) 0.056(3) Uani 1 1 d . . . H9A H 0.4994 0.4547 0.1278 0.085 Uiso 1 1 d R . . H9B H 0.3779 0.4296 0.2120 0.085 Uiso 1 1 d R . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 C1 0.069(11) 0.037(8) 0.029(8) 0.000(7) -0.018(7) 0.012(8) C2 0.046(9) 0.053(9) 0.023(7) -0.021(7) 0.006(6) 0.008(7) C3 0.020(7) 0.033(7) 0.012(6) 0.007(5) 0.002(5) 0.000(5) C4 0.030(8) 0.038(8) 0.026(8) 0.001(6) 0.000(6) 0.005(6) C5 0.037(9) 0.047(9) 0.039(9) -0.010(7) -0.013(7) -0.001(7) C6 0.043(9) 0.026(7) 0.012(7) 0.006(5) 0.007(6) -0.002(6) C7 0.024(7) 0.026(6) 0.019(6) -0.002(5) -0.010(5) 0.007(5) C8 0.023(7) 0.021(6) 0.013(6) -0.005(5) -0.001(5) 0.000(5) C9 0.032(5) 0.016(4) 0.013(5) 0.001(3) 0.000(4) 0.003(4) C10 0.010(6) 0.015(6) 0.020(7) 0.003(5) 0.000(5) -0.005(5) C11 0.032(5) 0.016(4) 0.013(5) 0.001(3) 0.000(4) 0.003(4) Tb1 0.0221(3) 0.0138(3) 0.0082(3) 0.0003(3) -0.0013(2) 0.0023(3) N1 0.016(5) 0.027(6) 0.014(6) -0.002(4) 0.005(4) 0.005(4) N2 0.028(6) 0.015(5) 0.022(6) -0.002(4) -0.006(4) 0.010(4) N3 0.035(7) 0.058(8) 0.012(6) -0.002(5) -0.004(5) 0.011(6) O1 0.040(6) 0.016(4) 0.015(5) -0.005(3) -0.004(4) 0.005(4) O2 0.028(5) 0.021(4) 0.019(5) -0.005(3) -0.006(4) 0.004(4) O3 0.045(6) 0.029(5) 0.017(5) -0.001(4) -0.001(4) 0.016(4) O4 0.054(6) 0.027(5) 0.024(5) -0.012(4) -0.019(4) 0.019(4) O5 0.037(6) 0.037(5) 0.028(5) 0.015(4) -0.021(4) -0.008(4) O6 0.047(4) 0.034(4) 0.007(3) -0.007(2) -0.006(3) 0.021(3) O7 0.047(4) 0.034(4) 0.007(3) -0.007(2) -0.006(3) 0.021(3) O8 0.058(7) 0.033(5) 0.021(5) -0.003(4) -0.015(5) 0.016(4) O9 0.076(8) 0.050(7) 0.043(7) -0.007(5) -0.011(6) -0.023(6) _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 C1 N3 1.326(16) . ? C1 C2 1.371(17) . ? C1 H1 0.9300 . ? C2 C3 1.372(17) . ? C2 H2 0.9300 . ? C3 C4 1.419(16) . ? C3 C6 1.478(15) . ? C4 C5 1.383(16) . ? C4 H4 0.9300 . ? C5 N3 1.326(16) . ? C5 H5 0.9300 . ? C6 N1 1.305(14) . ? C6 N2 1.357(14) . ? C7 C8 1.370(15) . ? C7 N2 1.373(12) . ? C7 C9 1.496(15) . ? C8 N1 1.397(13) . ? C8 C10 1.489(14) . ? C9 O3 1.248(12) . ? C9 O4 1.249(12) . ? C10 O2 1.240(12) . ? C10 O1 1.266(12) . ? C11 O6 1.257(13) . ? C11 O7 1.260(13) . ? C11 C11 1.54(2) 3_655 ? Tb1 O3 2.280(8) 4_565 ? Tb1 O2 2.339(7) 4_565 ? Tb1 O4 2.370(8) 2_545 ? Tb1 O1 2.375(7) . ? Tb1 O5 2.378(8) . ? Tb1 O6 2.410(7) 3_655 ? Tb1 O7 2.411(7) . ? Tb1 N1 2.525(9) . ? N2 H2A 0.8600 . ? O2 Tb1 2.339(7) 4_566 ? O3 Tb1 2.280(8) 4_566 ? O4 Tb1 2.370(8) 2 ? O5 H5A 0.8500 . ? O5 H5B 0.8501 . ? O6 Tb1 2.410(7) 3_655 ? O8 H8A 0.8501 . ? O8 H8B 0.8500 . ? O9 H9A 0.8500 . ? O9 H9B 0.8500 . ? 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 N3 C1 C2 123.1(13) . . ? N3 C1 H1 118.4 . . ? C2 C1 H1 118.4 . . ? C1 C2 C3 120.2(13) . . ? C1 C2 H2 119.9 . . ? C3 C2 H2 119.9 . . ? C2 C3 C4 116.6(11) . . ? C2 C3 C6 123.6(11) . . ? C4 C3 C6 119.8(10) . . ? C5 C4 C3 119.1(12) . . ? C5 C4 H4 120.5 . . ? C3 C4 H4 120.5 . . ? N3 C5 C4 122.5(13) . . ? N3 C5 H5 118.8 . . ? C4 C5 H5 118.8 . . ? N1 C6 N2 112.4(10) . . ? N1 C6 C3 128.9(11) . . ? N2 C6 C3 118.1(11) . . ? C8 C7 N2 105.3(9) . . ? C8 C7 C9 134.8(10) . . ? N2 C7 C9 118.8(9) . . ? C7 C8 N1 110.1(9) . . ? C7 C8 C10 133.7(10) . . ? N1 C8 C10 116.2(9) . . ? O3 C9 O4 126.6(11) . . ? O3 C9 C7 118.1(10) . . ? O4 C9 C7 115.2(10) . . ? O2 C10 O1 123.5(10) . . ? O2 C10 C8 122.2(10) . . ? O1 C10 C8 114.4(10) . . ? O6 C11 O7 126.2(10) . . ? O6 C11 C11 117.0(13) . 3_655 ? O7 C11 C11 116.8(12) . 3_655 ? O3 Tb1 O2 75.7(3) 4_565 4_565 ? O3 Tb1 O4 76.4(3) 4_565 2_545 ? O2 Tb1 O4 152.1(3) 4_565 2_545 ? O3 Tb1 O1 128.8(3) 4_565 . ? O2 Tb1 O1 126.7(2) 4_565 . ? O4 Tb1 O1 71.5(3) 2_545 . ? O3 Tb1 O5 147.7(3) 4_565 . ? O2 Tb1 O5 72.0(3) 4_565 . ? O4 Tb1 O5 135.9(3) 2_545 . ? O1 Tb1 O5 74.1(3) . . ? O3 Tb1 O6 78.3(3) 4_565 3_655 ? O2 Tb1 O6 76.5(3) 4_565 3_655 ? O4 Tb1 O6 99.6(3) 2_545 3_655 ? O1 Tb1 O6 145.0(3) . 3_655 ? O5 Tb1 O6 93.0(3) . 3_655 ? O3 Tb1 O7 128.7(3) 4_565 . ? O2 Tb1 O7 127.7(3) 4_565 . ? O4 Tb1 O7 73.1(3) 2_545 . ? O1 Tb1 O7 77.5(3) . . ? O5 Tb1 O7 73.2(3) . . ? O6 Tb1 O7 67.6(2) 3_655 . ? O3 Tb1 N1 84.2(3) 4_565 . ? O2 Tb1 N1 74.1(3) 4_565 . ? O4 Tb1 N1 101.3(3) 2_545 . ? O1 Tb1 N1 64.8(3) . . ? O5 Tb1 N1 88.1(3) . . ? O6 Tb1 N1 148.7(3) 3_655 . ? O7 Tb1 N1 141.4(3) . . ? C6 N1 C8 104.8(9) . . ? C6 N1 Tb1 138.0(8) . . ? C8 N1 Tb1 114.5(7) . . ? C6 N2 C7 107.4(9) . . ? C6 N2 H2A 126.3 . . ? C7 N2 H2A 126.3 . . ? C5 N3 C1 118.4(11) . . ? C10 O1 Tb1 125.9(7) . . ? C10 O2 Tb1 152.0(7) . 4_566 ? C9 O3 Tb1 145.7(8) . 4_566 ? C9 O4 Tb1 137.8(7) . 2 ? Tb1 O5 H5A 114.6 . . ? Tb1 O5 H5B 117.8 . . ? H5A O5 H5B 116.8 . . ? C11 O6 Tb1 119.3(7) . 3_655 ? C11 O7 Tb1 119.3(7) . . ? H8A O8 H8B 116.3 . . ? H9A O9 H9B 118.0 . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag N3 C1 C2 C3 -2(2) . . . . ? C1 C2 C3 C4 4.1(19) . . . . ? C1 C2 C3 C6 -177.9(13) . . . . ? C2 C3 C4 C5 -4.3(18) . . . . ? C6 C3 C4 C5 177.6(12) . . . . ? C3 C4 C5 N3 3(2) . . . . ? C2 C3 C6 N1 -127.7(14) . . . . ? C4 C3 C6 N1 50.3(19) . . . . ? C2 C3 C6 N2 61.6(17) . . . . ? C4 C3 C6 N2 -120.5(13) . . . . ? N2 C7 C8 N1 0.5(13) . . . . ? C9 C7 C8 N1 168.0(12) . . . . ? N2 C7 C8 C10 -179.3(12) . . . . ? C9 C7 C8 C10 -12(2) . . . . ? C8 C7 C9 O3 -3(2) . . . . ? N2 C7 C9 O3 162.8(11) . . . . ? C8 C7 C9 O4 180.0(13) . . . . ? N2 C7 C9 O4 -13.7(16) . . . . ? C7 C8 C10 O2 0(2) . . . . ? N1 C8 C10 O2 -179.8(10) . . . . ? C7 C8 C10 O1 -179.6(13) . . . . ? N1 C8 C10 O1 0.7(15) . . . . ? N2 C6 N1 C8 -0.6(14) . . . . ? C3 C6 N1 C8 -171.7(12) . . . . ? N2 C6 N1 Tb1 -159.8(8) . . . . ? C3 C6 N1 Tb1 29(2) . . . . ? C7 C8 N1 C6 0.0(14) . . . . ? C10 C8 N1 C6 179.8(10) . . . . ? C7 C8 N1 Tb1 164.9(8) . . . . ? C10 C8 N1 Tb1 -15.3(12) . . . . ? O3 Tb1 N1 C6 -48.0(12) 4_565 . . . ? O2 Tb1 N1 C6 28.8(12) 4_565 . . . ? O4 Tb1 N1 C6 -122.8(12) 2_545 . . . ? O1 Tb1 N1 C6 174.0(13) . . . . ? O5 Tb1 N1 C6 100.6(12) . . . . ? O6 Tb1 N1 C6 8.0(15) 3_655 . . . ? O7 Tb1 N1 C6 160.3(11) . . . . ? O3 Tb1 N1 C8 154.2(8) 4_565 . . . ? O2 Tb1 N1 C8 -129.0(8) 4_565 . . . ? O4 Tb1 N1 C8 79.3(8) 2_545 . . . ? O1 Tb1 N1 C8 16.1(7) . . . . ? O5 Tb1 N1 C8 -57.2(8) . . . . ? O6 Tb1 N1 C8 -149.8(7) 3_655 . . . ? O7 Tb1 N1 C8 2.4(10) . . . . ? N1 C6 N2 C7 0.9(14) . . . . ? C3 C6 N2 C7 173.1(10) . . . . ? C8 C7 N2 C6 -0.8(13) . . . . ? C9 C7 N2 C6 -170.7(11) . . . . ? C4 C5 N3 C1 -1(2) . . . . ? C2 C1 N3 C5 1(2) . . . . ? O2 C10 O1 Tb1 -162.3(8) . . . . ? C8 C10 O1 Tb1 17.1(13) . . . . ? O3 Tb1 O1 C10 -77.2(9) 4_565 . . . ? O2 Tb1 O1 C10 24.6(10) 4_565 . . . ? O4 Tb1 O1 C10 -131.3(9) 2_545 . . . ? O5 Tb1 O1 C10 76.8(9) . . . . ? O6 Tb1 O1 C10 148.6(8) 3_655 . . . ? O7 Tb1 O1 C10 152.6(9) . . . . ? N1 Tb1 O1 C10 -18.7(8) . . . . ? O1 C10 O2 Tb1 174.1(10) . . . 4_566 ? C8 C10 O2 Tb1 -5(2) . . . 4_566 ? O4 C9 O3 Tb1 -124.4(13) . . . 4_566 ? C7 C9 O3 Tb1 59.5(18) . . . 4_566 ? O3 C9 O4 Tb1 0(2) . . . 2 ? C7 C9 O4 Tb1 176.4(8) . . . 2 ? O7 C11 O6 Tb1 179.2(9) . . . 3_655 ? C11 C11 O6 Tb1 0.2(17) 3_655 . . 3_655 ? O6 C11 O7 Tb1 179.8(9) . . . . ? C11 C11 O7 Tb1 -1.1(17) 3_655 . . . ? O3 Tb1 O7 C11 53.0(10) 4_565 . . . ? O2 Tb1 O7 C11 -49.7(9) 4_565 . . . ? O4 Tb1 O7 C11 109.1(9) 2_545 . . . ? O1 Tb1 O7 C11 -176.7(9) . . . . ? O5 Tb1 O7 C11 -99.8(9) . . . . ? O6 Tb1 O7 C11 0.8(8) 3_655 . . . ? N1 Tb1 O7 C11 -164.1(8) . . . . ? 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 N2 H2A O8 0.86 1.97 2.824(11) 170.4 1_455 O9 H9B O6 0.85 2.34 3.159(12) 162.9 2_655 O5 H5B N3 0.85 1.90 2.751(12) 173.4 4_666 O8 H8B O9 0.85 2.04 2.876(12) 167.5 3_665 O8 H8A O1 0.85 1.89 2.734(11) 170.5 2_655 O5 H5A O9 0.85 2.08 2.868(12) 154.3 . O9 H9A O8 0.85 1.97 2.816(13) 178.6 . _diffrn_measured_fraction_theta_max 0.997 _diffrn_reflns_theta_full 25.50 _diffrn_measured_fraction_theta_full 0.997 _refine_diff_density_max 1.561 _refine_diff_density_min -2.105 _refine_diff_density_rms 0.245 data_2 _database_code_depnum_ccdc_archive 'CCDC 865493' #TrackingRef '- 2.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C11 H11 Eu N3 O9' _chemical_formula_weight 481.19 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Eu Eu -0.1578 3.6682 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Monoclinic _symmetry_space_group_name_H-M P2(1)/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 8.2862(17) _cell_length_b 14.865(3) _cell_length_c 11.559(2) _cell_angle_alpha 90.00 _cell_angle_beta 90.870(3) _cell_angle_gamma 90.00 _cell_volume 1423.7(5) _cell_formula_units_Z 4 _cell_measurement_temperature 298(2) _cell_measurement_reflns_used 1736 _cell_measurement_theta_min 2.232 _cell_measurement_theta_max 25.893 _exptl_crystal_description needle _exptl_crystal_colour colourless _exptl_crystal_size_max 0.32 _exptl_crystal_size_mid 0.06 _exptl_crystal_size_min 0.03 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 2.245 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 932 _exptl_absorpt_coefficient_mu 4.463 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.3293 _exptl_absorpt_correction_T_max 0.8777 _exptl_absorpt_process_details sadsabs _exptl_special_details ; ? ; _diffrn_ambient_temperature 298(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'CCD area detector' _diffrn_measurement_method 'phi and omega scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 7315 _diffrn_reflns_av_R_equivalents 0.0481 _diffrn_reflns_av_sigmaI/netI 0.0588 _diffrn_reflns_limit_h_min -9 _diffrn_reflns_limit_h_max 10 _diffrn_reflns_limit_k_min -8 _diffrn_reflns_limit_k_max 18 _diffrn_reflns_limit_l_min -14 _diffrn_reflns_limit_l_max 14 _diffrn_reflns_theta_min 2.23 _diffrn_reflns_theta_max 25.50 _reflns_number_total 2638 _reflns_number_gt 2279 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SMART' _computing_data_reduction 'Bruker SAINT' _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^)+(0.0261P)^2^+4.0067P] 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 2638 _refine_ls_number_parameters 217 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0498 _refine_ls_R_factor_gt 0.0402 _refine_ls_wR_factor_ref 0.0818 _refine_ls_wR_factor_gt 0.0782 _refine_ls_goodness_of_fit_ref 1.057 _refine_ls_restrained_S_all 1.057 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group C1 C -0.2370(10) 0.3672(5) -0.2151(6) 0.0349(19) Uani 1 1 d . . . H1 H -0.2348 0.4124 -0.2707 0.042 Uiso 1 1 calc R . . C2 C -0.1440(9) 0.3776(5) -0.1148(6) 0.0268(17) Uani 1 1 d . . . H2 H -0.0793 0.4282 -0.1046 0.032 Uiso 1 1 calc R . . C3 C -0.1489(8) 0.3121(5) -0.0310(5) 0.0200(15) Uani 1 1 d . . . C4 C -0.2442(9) 0.2377(5) -0.0511(6) 0.0294(18) Uani 1 1 d . . . H4 H -0.2487 0.1915 0.0030 0.035 Uiso 1 1 calc R . . C5 C -0.3332(9) 0.2329(5) -0.1532(7) 0.0325(19) Uani 1 1 d . . . H5 H -0.3995 0.1833 -0.1653 0.039 Uiso 1 1 calc R . . C6 C -0.0622(8) 0.3205(5) 0.0810(6) 0.0180(15) Uani 1 1 d . . . C7 C -0.0078(8) 0.3754(4) 0.2538(5) 0.0186(15) Uani 1 1 d . . . C8 C 0.0709(8) 0.2944(4) 0.2385(5) 0.0140(14) Uani 1 1 d . . . C9 C -0.0360(8) 0.4349(5) 0.3536(6) 0.0207(16) Uani 1 1 d . . . C10 C 0.1786(7) 0.2389(4) 0.3152(5) 0.0143(14) Uani 1 1 d . . . C11 C 0.5252(8) -0.0019(5) 0.0627(6) 0.0238(16) Uani 1 1 d . . . Eu1 Eu 0.21980(4) 0.13185(2) 0.06767(3) 0.01300(12) Uani 1 1 d . . . N1 N 0.0356(6) 0.2603(4) 0.1304(4) 0.0155(12) Uani 1 1 d . . . N2 N -0.0888(7) 0.3909(4) 0.1518(4) 0.0204(13) Uani 1 1 d . . . H2A H -0.1466 0.4374 0.1356 0.024 Uiso 1 1 calc R . . N3 N -0.3285(8) 0.2958(5) -0.2347(5) 0.0323(16) Uani 1 1 d . . . O1 O 0.2252(5) 0.1664(3) 0.2702(4) 0.0194(10) Uani 1 1 d . . . O2 O 0.2174(6) 0.2644(3) 0.4140(4) 0.0214(11) Uani 1 1 d . . . O3 O 0.0043(6) 0.4103(3) 0.4527(4) 0.0238(11) Uani 1 1 d . . . O4 O -0.1076(7) 0.5078(3) 0.3294(4) 0.0347(14) Uani 1 1 d . . . O5 O 0.4398(6) 0.2352(3) 0.0980(4) 0.0308(13) Uani 1 1 d . . . H5A H 0.4162 0.2906 0.0918 0.046 Uiso 1 1 d R . . H5B H 0.5097 0.2213 0.1488 0.046 Uiso 1 1 d R . . O6 O 0.6456(6) -0.0514(4) 0.0872(4) 0.0324(13) Uani 1 1 d . . . O7 O 0.4478(7) 0.0425(4) 0.1338(4) 0.0380(14) Uani 1 1 d . . . O8 O 0.6943(7) 0.5273(3) 0.0846(4) 0.0397(15) Uani 1 1 d . . . H8A H 0.7288 0.5668 0.1316 0.060 Uiso 1 1 d R . . H8B H 0.6779 0.5448 0.0155 0.060 Uiso 1 1 d R . . O9 O 0.4201(8) 0.4246(4) 0.1448(5) 0.0512(17) Uani 1 1 d . . . H9A H 0.5029 0.4553 0.1282 0.077 Uiso 1 1 d R . . H9B H 0.3821 0.4302 0.2118 0.077 Uiso 1 1 d R . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 C1 0.045(5) 0.035(5) 0.024(4) 0.008(4) -0.014(4) 0.013(4) C2 0.028(4) 0.025(4) 0.027(4) 0.001(3) -0.005(3) 0.008(3) C3 0.017(4) 0.030(4) 0.013(3) -0.007(3) -0.003(3) 0.006(3) C4 0.030(4) 0.029(4) 0.030(4) 0.003(3) -0.006(3) 0.001(3) C5 0.029(4) 0.036(5) 0.032(4) -0.003(4) -0.013(4) -0.007(4) C6 0.016(4) 0.023(4) 0.015(3) 0.000(3) -0.001(3) 0.003(3) C7 0.029(4) 0.018(4) 0.009(3) -0.003(3) -0.008(3) 0.002(3) C8 0.019(4) 0.012(3) 0.010(3) 0.002(3) -0.003(3) -0.001(3) C9 0.022(4) 0.019(4) 0.021(4) -0.006(3) -0.005(3) 0.006(3) C10 0.014(3) 0.014(3) 0.015(4) 0.002(3) 0.003(3) 0.001(3) C11 0.021(4) 0.016(4) 0.034(4) 0.001(3) 0.002(3) -0.001(3) Eu1 0.01760(19) 0.01139(18) 0.00996(17) -0.00026(14) -0.00146(12) 0.00162(14) N1 0.018(3) 0.021(3) 0.008(3) -0.005(2) -0.002(2) 0.004(2) N2 0.028(3) 0.018(3) 0.015(3) -0.005(2) -0.005(2) 0.008(3) N3 0.032(4) 0.042(4) 0.023(3) -0.008(3) -0.012(3) 0.011(3) O1 0.027(3) 0.016(2) 0.015(2) -0.002(2) -0.006(2) 0.009(2) O2 0.030(3) 0.018(3) 0.017(3) -0.007(2) -0.006(2) 0.007(2) O3 0.034(3) 0.022(3) 0.016(2) -0.002(2) -0.003(2) 0.009(2) O4 0.056(4) 0.029(3) 0.019(3) -0.009(2) -0.013(2) 0.028(3) O5 0.027(3) 0.034(3) 0.031(3) 0.014(2) -0.016(2) -0.008(2) O6 0.030(3) 0.044(3) 0.023(3) -0.003(2) -0.007(2) 0.020(3) O7 0.041(3) 0.051(4) 0.022(3) -0.008(3) -0.008(2) 0.029(3) O8 0.059(4) 0.028(3) 0.032(3) -0.005(2) -0.019(3) 0.007(3) O9 0.070(5) 0.043(4) 0.041(4) -0.007(3) -0.011(3) -0.009(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 C1 N3 1.322(10) . ? C1 C2 1.391(10) . ? C1 H1 0.9300 . ? C2 C3 1.374(10) . ? C2 H2 0.9300 . ? C3 C4 1.377(10) . ? C3 C6 1.477(8) . ? C4 C5 1.384(9) . ? C4 H4 0.9300 . ? C5 N3 1.327(10) . ? C5 H5 0.9300 . ? C6 N1 1.331(8) . ? C6 N2 1.348(8) . ? C7 N2 1.367(7) . ? C7 C8 1.382(9) . ? C7 C9 1.475(9) . ? C8 N1 1.376(7) . ? C8 C10 1.496(8) . ? C9 O3 1.243(8) . ? C9 O4 1.265(8) . ? C10 O2 1.241(7) . ? C10 O1 1.260(7) . ? C11 O7 1.241(8) . ? C11 O6 1.269(8) . ? C11 C11 1.503(14) 3_655 ? C11 Eu1 3.250(7) 3_655 ? Eu1 O3 2.297(4) 4_565 ? Eu1 O2 2.352(4) 4_565 ? Eu1 O4 2.390(5) 2_545 ? Eu1 O1 2.397(4) . ? Eu1 O5 2.406(5) . ? Eu1 O7 2.424(5) . ? Eu1 O6 2.437(5) 3_655 ? Eu1 N1 2.556(5) . ? Eu1 C11 3.250(7) 3_655 ? N2 H2A 0.8600 . ? O2 Eu1 2.352(4) 4_566 ? O3 Eu1 2.297(4) 4_566 ? O4 Eu1 2.390(5) 2 ? O5 H5A 0.8496 . ? O5 H5B 0.8444 . ? O6 Eu1 2.437(5) 3_655 ? O8 H8A 0.8459 . ? O8 H8B 0.8490 . ? O9 H9A 0.8477 . ? O9 H9B 0.8454 . ? 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 N3 C1 C2 122.8(7) . . ? N3 C1 H1 118.6 . . ? C2 C1 H1 118.6 . . ? C3 C2 C1 119.1(7) . . ? C3 C2 H2 120.4 . . ? C1 C2 H2 120.4 . . ? C2 C3 C4 118.3(6) . . ? C2 C3 C6 122.6(6) . . ? C4 C3 C6 119.1(6) . . ? C3 C4 C5 118.8(7) . . ? C3 C4 H4 120.6 . . ? C5 C4 H4 120.6 . . ? N3 C5 C4 123.2(7) . . ? N3 C5 H5 118.4 . . ? C4 C5 H5 118.4 . . ? N1 C6 N2 111.4(5) . . ? N1 C6 C3 127.2(6) . . ? N2 C6 C3 121.1(6) . . ? N2 C7 C8 105.3(5) . . ? N2 C7 C9 119.5(6) . . ? C8 C7 C9 134.7(6) . . ? N1 C8 C7 110.0(5) . . ? N1 C8 C10 116.9(5) . . ? C7 C8 C10 133.1(6) . . ? O3 C9 O4 125.0(6) . . ? O3 C9 C7 120.1(6) . . ? O4 C9 C7 114.9(6) . . ? O2 C10 O1 124.4(6) . . ? O2 C10 C8 121.4(6) . . ? O1 C10 C8 114.2(5) . . ? O7 C11 O6 125.0(6) . . ? O7 C11 C11 118.7(8) . 3_655 ? O6 C11 C11 116.4(8) . 3_655 ? O7 C11 Eu1 165.9(5) . 3_655 ? O6 C11 Eu1 40.9(3) . 3_655 ? C11 C11 Eu1 75.5(5) 3_655 3_655 ? O3 Eu1 O2 75.18(15) 4_565 4_565 ? O3 Eu1 O4 76.86(16) 4_565 2_545 ? O2 Eu1 O4 151.96(16) 4_565 2_545 ? O3 Eu1 O1 128.79(16) 4_565 . ? O2 Eu1 O1 126.64(15) 4_565 . ? O4 Eu1 O1 71.39(16) 2_545 . ? O3 Eu1 O5 147.05(16) 4_565 . ? O2 Eu1 O5 71.87(15) 4_565 . ? O4 Eu1 O5 136.06(16) 2_545 . ? O1 Eu1 O5 73.62(16) . . ? O3 Eu1 O7 128.93(18) 4_565 . ? O2 Eu1 O7 126.54(18) 4_565 . ? O4 Eu1 O7 74.19(19) 2_545 . ? O1 Eu1 O7 78.84(15) . . ? O5 Eu1 O7 73.68(19) . . ? O3 Eu1 O6 78.55(17) 4_565 3_655 ? O2 Eu1 O6 76.45(17) 4_565 3_655 ? O4 Eu1 O6 99.97(19) 2_545 3_655 ? O1 Eu1 O6 145.18(15) . 3_655 ? O5 Eu1 O6 93.78(18) . 3_655 ? O7 Eu1 O6 66.41(16) . 3_655 ? O3 Eu1 N1 84.59(17) 4_565 . ? O2 Eu1 N1 74.10(16) 4_565 . ? O4 Eu1 N1 101.33(19) 2_545 . ? O1 Eu1 N1 64.21(15) . . ? O5 Eu1 N1 86.32(17) . . ? O7 Eu1 N1 141.78(16) . . ? O6 Eu1 N1 148.95(16) 3_655 . ? O3 Eu1 C11 94.29(17) 4_565 3_655 ? O2 Eu1 C11 92.18(17) 4_565 3_655 ? O4 Eu1 C11 91.89(19) 2_545 3_655 ? O1 Eu1 C11 125.29(16) . 3_655 ? O5 Eu1 C11 87.16(17) . 3_655 ? O7 Eu1 C11 46.47(17) . 3_655 ? O6 Eu1 C11 19.93(16) 3_655 3_655 ? N1 Eu1 C11 166.08(17) . 3_655 ? C6 N1 C8 105.2(5) . . ? C6 N1 Eu1 138.0(4) . . ? C8 N1 Eu1 114.4(4) . . ? C6 N2 C7 108.1(5) . . ? C6 N2 H2A 126.0 . . ? C7 N2 H2A 126.0 . . ? C1 N3 C5 117.8(6) . . ? C10 O1 Eu1 125.8(4) . . ? C10 O2 Eu1 153.4(4) . 4_566 ? C9 O3 Eu1 144.0(5) . 4_566 ? C9 O4 Eu1 137.4(4) . 2 ? Eu1 O5 H5A 115.7 . . ? Eu1 O5 H5B 117.1 . . ? H5A O5 H5B 116.7 . . ? C11 O6 Eu1 119.2(4) . 3_655 ? C11 O7 Eu1 119.4(4) . . ? H8A O8 H8B 116.0 . . ? H9A O9 H9B 117.9 . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag N3 C1 C2 C3 -1.3(12) . . . . ? C1 C2 C3 C4 1.2(10) . . . . ? C1 C2 C3 C6 -176.0(7) . . . . ? C2 C3 C4 C5 -1.3(11) . . . . ? C6 C3 C4 C5 175.9(7) . . . . ? C3 C4 C5 N3 1.7(12) . . . . ? C2 C3 C6 N1 -129.7(8) . . . . ? C4 C3 C6 N1 53.1(10) . . . . ? C2 C3 C6 N2 57.0(10) . . . . ? C4 C3 C6 N2 -120.2(8) . . . . ? N2 C7 C8 N1 -1.3(7) . . . . ? C9 C7 C8 N1 169.1(7) . . . . ? N2 C7 C8 C10 -179.6(7) . . . . ? C9 C7 C8 C10 -9.2(13) . . . . ? N2 C7 C9 O3 162.6(6) . . . . ? C8 C7 C9 O3 -6.8(12) . . . . ? N2 C7 C9 O4 -14.8(10) . . . . ? C8 C7 C9 O4 175.8(7) . . . . ? N1 C8 C10 O2 179.8(6) . . . . ? C7 C8 C10 O2 -2.0(11) . . . . ? N1 C8 C10 O1 0.3(8) . . . . ? C7 C8 C10 O1 178.5(7) . . . . ? N2 C6 N1 C8 0.7(7) . . . . ? C3 C6 N1 C8 -173.2(7) . . . . ? N2 C6 N1 Eu1 -159.6(5) . . . . ? C3 C6 N1 Eu1 26.5(11) . . . . ? C7 C8 N1 C6 0.4(7) . . . . ? C10 C8 N1 C6 179.1(6) . . . . ? C7 C8 N1 Eu1 166.1(4) . . . . ? C10 C8 N1 Eu1 -15.3(7) . . . . ? O3 Eu1 N1 C6 -46.5(7) 4_565 . . . ? O2 Eu1 N1 C6 29.6(6) 4_565 . . . ? O4 Eu1 N1 C6 -122.0(7) 2_545 . . . ? O1 Eu1 N1 C6 175.3(7) . . . . ? O5 Eu1 N1 C6 101.7(7) . . . . ? O7 Eu1 N1 C6 159.3(6) . . . . ? O6 Eu1 N1 C6 10.5(8) 3_655 . . . ? C11 Eu1 N1 C6 39.5(11) 3_655 . . . ? O3 Eu1 N1 C8 154.4(4) 4_565 . . . ? O2 Eu1 N1 C8 -129.5(5) 4_565 . . . ? O4 Eu1 N1 C8 79.0(4) 2_545 . . . ? O1 Eu1 N1 C8 16.3(4) . . . . ? O5 Eu1 N1 C8 -57.3(4) . . . . ? O7 Eu1 N1 C8 0.2(6) . . . . ? O6 Eu1 N1 C8 -148.5(4) 3_655 . . . ? C11 Eu1 N1 C8 -119.5(7) 3_655 . . . ? N1 C6 N2 C7 -1.5(8) . . . . ? C3 C6 N2 C7 172.8(6) . . . . ? C8 C7 N2 C6 1.7(7) . . . . ? C9 C7 N2 C6 -170.5(6) . . . . ? C2 C1 N3 C5 1.6(12) . . . . ? C4 C5 N3 C1 -1.8(12) . . . . ? O2 C10 O1 Eu1 -161.5(5) . . . . ? C8 C10 O1 Eu1 17.9(8) . . . . ? O3 Eu1 O1 C10 -77.6(5) 4_565 . . . ? O2 Eu1 O1 C10 23.2(6) 4_565 . . . ? O4 Eu1 O1 C10 -132.3(5) 2_545 . . . ? O5 Eu1 O1 C10 74.7(5) . . . . ? O7 Eu1 O1 C10 150.8(5) . . . . ? O6 Eu1 O1 C10 147.1(5) 3_655 . . . ? N1 Eu1 O1 C10 -19.2(5) . . . . ? C11 Eu1 O1 C10 149.0(5) 3_655 . . . ? O1 C10 O2 Eu1 176.4(6) . . . 4_566 ? C8 C10 O2 Eu1 -3.0(14) . . . 4_566 ? O4 C9 O3 Eu1 -122.0(8) . . . 4_566 ? C7 C9 O3 Eu1 60.9(11) . . . 4_566 ? O3 C9 O4 Eu1 -4.2(12) . . . 2 ? C7 C9 O4 Eu1 173.0(5) . . . 2 ? O7 C11 O6 Eu1 -179.6(6) . . . 3_655 ? C11 C11 O6 Eu1 0.5(10) 3_655 . . 3_655 ? O6 C11 O7 Eu1 -179.5(5) . . . . ? C11 C11 O7 Eu1 0.3(11) 3_655 . . . ? Eu1 C11 O7 Eu1 179.4(18) 3_655 . . . ? O3 Eu1 O7 C11 50.4(6) 4_565 . . . ? O2 Eu1 O7 C11 -50.5(6) 4_565 . . . ? O4 Eu1 O7 C11 108.2(6) 2_545 . . . ? O1 Eu1 O7 C11 -178.2(6) . . . . ? O5 Eu1 O7 C11 -102.1(6) . . . . ? O6 Eu1 O7 C11 -0.4(5) 3_655 . . . ? N1 Eu1 O7 C11 -163.5(5) . . . . ? C11 Eu1 O7 C11 -0.2(6) 3_655 . . . ? 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 N2 H2A O8 0.86 1.96 2.811(7) 169.3 1_455 O9 H9B O6 0.85 2.35 3.174(8) 163.7 2_655 O5 H5B N3 0.84 1.90 2.744(7) 173.5 4_666 O8 H8B O9 0.85 2.06 2.892(7) 165.5 3_665 O8 H8A O1 0.85 1.90 2.739(7) 170.5 2_655 O5 H5A O9 0.85 2.08 2.871(7) 154.1 . O9 H9A O8 0.85 1.99 2.833(9) 178.3 . _diffrn_measured_fraction_theta_max 0.999 _diffrn_reflns_theta_full 25.50 _diffrn_measured_fraction_theta_full 0.999 _refine_diff_density_max 1.017 _refine_diff_density_min -1.609 _refine_diff_density_rms 0.171