# Electronic Supplementary Material (ESI) for Dalton Transactions # 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_abd032_0m _database_code_depnum_ccdc_archive 'CCDC 886729' #TrackingRef 'bpyNO2.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C20 H14 N6 O4' _chemical_formula_weight 402.37 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' _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M P21/n loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, y+1/2, -z+1/2' '-x, -y, -z' 'x-1/2, -y-1/2, z-1/2' _cell_length_a 3.7128(3) _cell_length_b 11.7806(8) _cell_length_c 19.9856(14) _cell_angle_alpha 90.00 _cell_angle_beta 92.925(2) _cell_angle_gamma 90.00 _cell_volume 873.01(11) _cell_formula_units_Z 2 _cell_measurement_temperature 100(2) _cell_measurement_reflns_used 572 _cell_measurement_theta_min 5.54 _cell_measurement_theta_max 30.50 _exptl_crystal_description needle _exptl_crystal_colour colourless _exptl_crystal_size_max 0.20 _exptl_crystal_size_mid 0.13 _exptl_crystal_size_min 0.13 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.531 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 416 _exptl_absorpt_coefficient_mu 0.111 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.8079 _exptl_absorpt_correction_T_max 0.9857 _exptl_absorpt_process_details 'SADABS SHELXL-97 (Sheldrick, 2001)' _exptl_special_details ; ? ; _diffrn_ambient_temperature 100(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'APEX CCD detector' _diffrn_measurement_method 'Phi and omega scans' _diffrn_detector_area_resol_mean 8.3 _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% 0.001 _diffrn_reflns_number 3218 _diffrn_reflns_av_R_equivalents 0.0243 _diffrn_reflns_av_sigmaI/netI 0.0304 _diffrn_reflns_limit_h_min -3 _diffrn_reflns_limit_h_max 4 _diffrn_reflns_limit_k_min -7 _diffrn_reflns_limit_k_max 14 _diffrn_reflns_limit_l_min -22 _diffrn_reflns_limit_l_max 23 _diffrn_reflns_theta_min 5.54 _diffrn_reflns_theta_max 25.00 _reflns_number_total 1453 _reflns_number_gt 1269 _reflns_threshold_expression >2\s(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^ > 2\s(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^)+(0.0873P)^2^+0.0836P] 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 refall _refine_ls_extinction_method SHELXL _refine_ls_extinction_coef 0.015(5) _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_number_reflns 1453 _refine_ls_number_parameters 165 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0393 _refine_ls_R_factor_gt 0.0338 _refine_ls_wR_factor_ref 0.1056 _refine_ls_wR_factor_gt 0.0987 _refine_ls_goodness_of_fit_ref 0.915 _refine_ls_restrained_S_all 0.915 _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 H1 H 0.355(4) 0.3595(13) -0.1353(8) 0.020(4) Uiso 1 1 d . . . H2 H 0.298(4) 0.1736(12) -0.1730(8) 0.024(4) Uiso 1 1 d . . . H3 H 0.509(4) 0.0225(14) -0.0997(8) 0.029(4) Uiso 1 1 d . . . H4 H 0.768(4) 0.0770(14) 0.0082(9) 0.027(4) Uiso 1 1 d . . . H7 H 0.839(4) 0.4541(14) 0.0454(9) 0.028(4) Uiso 1 1 d . . . H8 H 1.117(4) 0.5038(14) 0.1510(7) 0.022(4) Uiso 1 1 d . . . H9 H 1.271(4) 0.3538(13) 0.2279(8) 0.023(4) Uiso 1 1 d . . . C1 C 0.4321(4) 0.29943(12) -0.10765(7) 0.0218(4) Uani 1 1 d . . . C2 C 0.4014(4) 0.18825(12) -0.12914(7) 0.0227(4) Uani 1 1 d . . . C3 C 0.5245(4) 0.10300(12) -0.08641(7) 0.0225(3) Uani 1 1 d . . . C4 C 0.6729(4) 0.13260(12) -0.02401(7) 0.0203(4) Uani 1 1 d . . . C5 C 0.6917(3) 0.24660(10) -0.00593(6) 0.0173(3) Uani 1 1 d . . . C6 C 0.8488(3) 0.28227(11) 0.06059(6) 0.0175(3) Uani 1 1 d . . . C7 C 0.9091(4) 0.39693(12) 0.07659(7) 0.0204(3) Uani 1 1 d . . . C8 C 1.0669(4) 0.42473(12) 0.13842(7) 0.0218(3) Uani 1 1 d . . . C9 C 1.1599(4) 0.33958(11) 0.18401(7) 0.0205(4) Uani 1 1 d . . . C10 C 1.0838(4) 0.23035(11) 0.16287(6) 0.0182(3) Uani 1 1 d . . . N1 N 0.5733(3) 0.33064(9) -0.04757(6) 0.0214(3) Uani 1 1 d . . . N2 N 0.9342(3) 0.19902(9) 0.10467(5) 0.0180(3) Uani 1 1 d . . . N3 N 1.1742(3) 0.13502(10) 0.20981(5) 0.0206(3) Uani 1 1 d . . . O1 O 1.0378(3) 0.04204(8) 0.19905(5) 0.0297(3) Uani 1 1 d . . . O2 O 1.3845(3) 0.15663(8) 0.25785(5) 0.0289(3) Uani 1 1 d . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 C1 0.0185(8) 0.0301(8) 0.0170(7) 0.0052(6) 0.0014(5) 0.0020(6) C2 0.0168(7) 0.0355(8) 0.0160(7) -0.0006(6) 0.0034(5) -0.0032(6) C3 0.0230(8) 0.0261(7) 0.0189(7) -0.0022(6) 0.0056(5) -0.0028(6) C4 0.0192(8) 0.0241(7) 0.0179(7) 0.0023(6) 0.0041(5) 0.0011(5) C5 0.0129(7) 0.0239(7) 0.0157(7) 0.0013(5) 0.0059(5) 0.0000(5) C6 0.0133(7) 0.0221(7) 0.0176(7) 0.0013(5) 0.0054(5) 0.0000(5) C7 0.0187(8) 0.0226(7) 0.0200(7) 0.0023(6) 0.0034(5) 0.0006(5) C8 0.0198(8) 0.0220(7) 0.0238(7) -0.0026(5) 0.0043(6) -0.0019(5) C9 0.0165(8) 0.0274(7) 0.0180(7) -0.0034(6) 0.0035(6) -0.0009(5) C10 0.0151(7) 0.0248(7) 0.0152(7) -0.0005(5) 0.0039(5) 0.0007(5) N1 0.0194(6) 0.0256(6) 0.0191(6) 0.0034(5) 0.0013(5) 0.0007(4) N2 0.0154(6) 0.0228(6) 0.0162(6) -0.0007(4) 0.0038(4) 0.0009(4) N3 0.0225(7) 0.0256(6) 0.0140(6) -0.0001(4) 0.0026(5) 0.0024(5) O1 0.0407(7) 0.0220(5) 0.0260(6) 0.0020(4) -0.0020(5) -0.0018(4) O2 0.0331(7) 0.0348(6) 0.0178(5) 0.0015(4) -0.0062(4) 0.0014(4) _geom_special_details ; All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell s.u.'s are taken into account individually in the estimation of s.u.'s in distances, angles and torsion angles; correlations between s.u.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell s.u.'s is used for estimating s.u.'s 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 N1 1.3370(18) . ? C1 C2 1.381(2) . ? C1 H1 0.934(16) . ? C2 C3 1.381(2) . ? C2 H2 0.954(17) . ? C3 C4 1.382(2) . ? C3 H3 0.986(17) . ? C4 C5 1.3916(19) . ? C4 H4 0.971(18) . ? C5 N1 1.3524(17) . ? C5 C6 1.4848(19) . ? C6 N2 1.3454(18) . ? C6 C7 1.4035(19) . ? C7 C8 1.380(2) . ? C7 H7 0.945(17) . ? C8 C9 1.387(2) . ? C8 H8 0.980(16) . ? C9 C10 1.3791(18) . ? C9 H9 0.965(17) . ? C10 N2 1.3159(18) . ? C10 N3 1.4907(17) . ? N3 O1 1.2212(15) . ? N3 O2 1.2327(16) . ? 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 N1 C1 C2 124.22(13) . . ? N1 C1 H1 114.7(10) . . ? C2 C1 H1 121.1(10) . . ? C1 C2 C3 118.55(13) . . ? C1 C2 H2 118.7(9) . . ? C3 C2 H2 122.8(9) . . ? C2 C3 C4 118.60(13) . . ? C2 C3 H3 121.3(10) . . ? C4 C3 H3 120.1(10) . . ? C3 C4 C5 119.35(13) . . ? C3 C4 H4 122.8(10) . . ? C5 C4 H4 117.8(10) . . ? N1 C5 C4 122.43(13) . . ? N1 C5 C6 116.38(11) . . ? C4 C5 C6 121.19(12) . . ? N2 C6 C7 121.52(13) . . ? N2 C6 C5 116.66(11) . . ? C7 C6 C5 121.82(12) . . ? C8 C7 C6 119.21(13) . . ? C8 C7 H7 120.8(10) . . ? C6 C7 H7 120.0(10) . . ? C7 C8 C9 119.80(13) . . ? C7 C8 H8 121.5(9) . . ? C9 C8 H8 118.7(9) . . ? C10 C9 C8 115.67(13) . . ? C10 C9 H9 120.8(9) . . ? C8 C9 H9 123.5(9) . . ? N2 C10 C9 127.10(13) . . ? N2 C10 N3 114.60(11) . . ? C9 C10 N3 118.30(12) . . ? C1 N1 C5 116.85(12) . . ? C10 N2 C6 116.68(12) . . ? O1 N3 O2 124.26(11) . . ? O1 N3 C10 119.13(12) . . ? O2 N3 C10 116.61(11) . . ? _diffrn_measured_fraction_theta_max 0.939 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 0.939 _refine_diff_density_max 0.213 _refine_diff_density_min -0.215 _refine_diff_density_rms 0.044 data_abd090_011311_pbca _database_code_depnum_ccdc_archive 'CCDC 886730' #TrackingRef 'terpyNO2EuNO3.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C15 H10 Eu N7 O11' _chemical_formula_weight 616.26 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 orthorhombic _symmetry_space_group_name_H-M Pbca 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' '-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 15.1341(4) _cell_length_b 13.7070(4) _cell_length_c 18.8277(5) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 3905.68(19) _cell_formula_units_Z 8 _cell_measurement_temperature 100(2) _cell_measurement_reflns_used 9877 _cell_measurement_theta_min 2.28 _cell_measurement_theta_max 22.09 _exptl_crystal_description plate _exptl_crystal_colour colorless _exptl_crystal_size_max 0.18 _exptl_crystal_size_mid 0.11 _exptl_crystal_size_min 0.07 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 2.096 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 2400 _exptl_absorpt_coefficient_mu 3.292 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.5856 _exptl_absorpt_correction_T_max 0.8023 _exptl_absorpt_process_details 'SADABS SHELXL-97 (Sheldrick, 2001)' _exptl_special_details ; ? ; _diffrn_ambient_temperature 100(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Bruker APEX CCD' _diffrn_measurement_method 'phi and omega scans' _diffrn_detector_area_resol_mean ? _diffrn_reflns_number 130936 _diffrn_reflns_av_R_equivalents 0.0344 _diffrn_reflns_av_sigmaI/netI 0.0138 _diffrn_reflns_limit_h_min -23 _diffrn_reflns_limit_h_max 23 _diffrn_reflns_limit_k_min -20 _diffrn_reflns_limit_k_max 21 _diffrn_reflns_limit_l_min -28 _diffrn_reflns_limit_l_max 29 _diffrn_reflns_theta_min 2.16 _diffrn_reflns_theta_max 33.19 _reflns_number_total 7470 _reflns_number_gt 6312 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART (Bruker, 2001)' _computing_cell_refinement 'Bruker SMART (Bruker, 2001)' _computing_data_reduction 'Bruker SAINT (Bruker, 2001)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 2001)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2001)' _computing_molecular_graphics 'DIAMOND (Brandenburg, 1999)' _computing_publication_material 'Bruker SHELXTL (Bruker, 2001)' _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^)+(0.0349P)^2^+10.5582P] 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 noref _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 7470 _refine_ls_number_parameters 307 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0381 _refine_ls_R_factor_gt 0.0298 _refine_ls_wR_factor_ref 0.0823 _refine_ls_wR_factor_gt 0.0740 _refine_ls_goodness_of_fit_ref 1.078 _refine_ls_restrained_S_all 1.078 _refine_ls_shift/su_max 0.007 _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 Eu1 Eu 1.026701(7) 0.319265(9) 0.109213(6) 0.01699(4) Uani 1 1 d . . . C1 C 1.17914(19) 0.1766(2) 0.19484(18) 0.0303(6) Uani 1 1 d . . . H1 H 1.1978 0.1679 0.1471 0.036 Uiso 1 1 calc R . . C2 C 1.23068(19) 0.1373(2) 0.24861(18) 0.0338(6) Uani 1 1 d . . . H2 H 1.2842 0.1042 0.2379 0.041 Uiso 1 1 calc R . . C3 C 1.2027(2) 0.1470(2) 0.31785(18) 0.0333(6) Uani 1 1 d . . . H3 H 1.2366 0.1209 0.3558 0.040 Uiso 1 1 calc R . . C4 C 1.1240(2) 0.1957(2) 0.33127(16) 0.0285(5) Uani 1 1 d . . . H4 H 1.1022 0.2013 0.3784 0.034 Uiso 1 1 calc R . . C5 C 1.07734(16) 0.23624(17) 0.27487(13) 0.0204(4) Uani 1 1 d . . . C6 C 0.99414(16) 0.29058(18) 0.28657(13) 0.0199(4) Uani 1 1 d . . . C7 C 0.96400(18) 0.3130(2) 0.35465(15) 0.0248(5) Uani 1 1 d . . . H7 H 0.9986 0.2971 0.3951 0.030 Uiso 1 1 calc R . . C8 C 0.88356(19) 0.3585(2) 0.36245(14) 0.0274(5) Uani 1 1 d . . . H8 H 0.8623 0.3749 0.4084 0.033 Uiso 1 1 calc R . . C9 C 0.83373(17) 0.3803(2) 0.30276(14) 0.0243(5) Uani 1 1 d . . . H9 H 0.7771 0.4095 0.3072 0.029 Uiso 1 1 calc R . . C10 C 0.86816(15) 0.35871(17) 0.23647(13) 0.0188(4) Uani 1 1 d . . . C11 C 0.81793(15) 0.37770(17) 0.17042(13) 0.0190(4) Uani 1 1 d . . . C12 C 0.73037(15) 0.41017(19) 0.17121(15) 0.0232(4) Uani 1 1 d . . . H12 H 0.7015 0.4224 0.2151 0.028 Uiso 1 1 calc R . . C13 C 0.68604(17) 0.4244(2) 0.10781(15) 0.0275(5) Uani 1 1 d . . . H13 H 0.6266 0.4468 0.1078 0.033 Uiso 1 1 calc R . . C14 C 0.72902(17) 0.4056(2) 0.04434(16) 0.0267(5) Uani 1 1 d . . . H14 H 0.7006 0.4133 -0.0003 0.032 Uiso 1 1 calc R . . C15 C 0.81531(16) 0.37502(19) 0.04967(14) 0.0230(4) Uani 1 1 d . . . N1 N 1.10405(14) 0.22636(16) 0.20699(12) 0.0230(4) Uani 1 1 d . . . N2 N 0.94828(14) 0.31660(15) 0.22813(11) 0.0183(3) Uani 1 1 d . . . N3 N 0.85999(14) 0.36028(16) 0.10927(11) 0.0199(4) Uani 1 1 d . . . N4 N 0.86736(17) 0.3580(2) -0.01553(13) 0.0302(5) Uani 1 1 d . . . N5 N 1.00304(18) 0.1154(2) 0.07723(17) 0.0346(6) Uani 1 1 d . . . N6 N 1.18542(16) 0.3632(2) 0.02438(12) 0.0296(5) Uani 1 1 d . . . N7 N 1.05449(15) 0.50618(17) 0.17885(14) 0.0272(5) Uani 1 1 d . . . O1 O 0.94480(16) 0.3304(2) -0.00859(12) 0.0385(5) Uani 1 1 d . . . O2 O 0.83287(15) 0.3720(2) -0.07260(12) 0.0383(5) Uani 1 1 d . . . O3 O 1.06422(14) 0.16703(16) 0.04795(15) 0.0370(5) Uani 1 1 d . . . O4 O 0.94356(15) 0.16336(17) 0.11006(12) 0.0321(5) Uani 1 1 d . . . O5 O 1.00432(19) 0.02746(19) 0.0750(2) 0.0554(8) Uani 1 1 d . . . O6 O 1.18767(13) 0.31067(16) 0.07799(12) 0.0307(4) Uani 1 1 d . . . O7 O 1.11210(15) 0.4062(2) 0.01231(13) 0.0417(6) Uani 1 1 d . . . O8 O 1.25101(15) 0.3773(2) -0.01221(12) 0.0475(7) Uani 1 1 d . . . O9 O 1.10903(12) 0.43618(14) 0.18340(10) 0.0241(4) Uani 1 1 d . . . O10 O 0.99353(15) 0.49517(16) 0.13350(14) 0.0337(5) Uani 1 1 d . . . O11 O 1.06207(16) 0.57764(17) 0.21682(16) 0.0443(6) Uani 1 1 d . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 Eu1 0.01271(6) 0.02044(6) 0.01783(6) -0.00013(4) 0.00030(3) 0.00030(4) C1 0.0223(12) 0.0267(13) 0.0419(15) 0.0127(11) 0.0092(11) 0.0082(10) C2 0.0237(13) 0.0253(13) 0.0524(18) 0.0069(12) -0.0009(12) 0.0074(10) C3 0.0347(15) 0.0217(12) 0.0435(16) -0.0015(11) -0.0153(12) 0.0058(11) C4 0.0326(14) 0.0220(11) 0.0310(13) -0.0021(9) -0.0118(11) 0.0044(10) C5 0.0186(9) 0.0164(9) 0.0263(10) 0.0022(8) -0.0022(8) -0.0006(8) C6 0.0179(9) 0.0182(10) 0.0237(10) 0.0021(8) -0.0005(8) -0.0014(8) C7 0.0236(12) 0.0290(12) 0.0219(11) 0.0022(9) 0.0004(9) -0.0029(9) C8 0.0259(12) 0.0326(13) 0.0237(11) -0.0026(10) 0.0048(9) -0.0041(10) C9 0.0184(10) 0.0283(12) 0.0262(11) -0.0022(9) 0.0058(9) -0.0007(9) C10 0.0138(9) 0.0192(10) 0.0233(10) -0.0013(8) 0.0018(7) -0.0008(7) C11 0.0141(9) 0.0175(9) 0.0253(10) -0.0004(8) 0.0003(8) -0.0017(7) C12 0.0136(9) 0.0226(11) 0.0332(12) 0.0019(9) 0.0022(8) -0.0007(8) C13 0.0148(10) 0.0281(12) 0.0397(14) 0.0036(10) -0.0019(9) 0.0002(9) C14 0.0181(10) 0.0274(12) 0.0345(13) 0.0019(10) -0.0083(9) -0.0037(9) C15 0.0178(10) 0.0261(11) 0.0250(11) -0.0024(9) -0.0053(8) -0.0015(8) N1 0.0179(9) 0.0217(10) 0.0293(10) 0.0078(8) 0.0047(8) 0.0037(7) N2 0.0145(8) 0.0195(9) 0.0209(9) -0.0003(7) 0.0002(7) -0.0001(7) N3 0.0158(8) 0.0218(9) 0.0221(9) -0.0027(7) -0.0026(7) -0.0013(7) N4 0.0255(11) 0.0414(14) 0.0237(10) -0.0053(9) -0.0073(8) -0.0015(10) N5 0.0232(11) 0.0295(12) 0.0511(16) -0.0083(11) 0.0063(11) -0.0027(9) N6 0.0202(10) 0.0458(14) 0.0227(10) 0.0081(9) 0.0028(8) -0.0009(10) N7 0.0194(9) 0.0193(9) 0.0430(13) 0.0011(9) -0.0041(9) -0.0008(8) O1 0.0267(10) 0.0651(16) 0.0237(9) -0.0094(10) -0.0046(8) 0.0095(10) O2 0.0326(11) 0.0571(15) 0.0252(9) -0.0033(9) -0.0125(8) -0.0017(10) O3 0.0233(10) 0.0314(10) 0.0564(14) -0.0135(10) 0.0169(10) -0.0048(8) O4 0.0215(9) 0.0298(10) 0.0452(13) -0.0090(9) 0.0097(8) -0.0030(8) O5 0.0397(13) 0.0252(12) 0.101(3) -0.0138(14) 0.0190(16) -0.0050(10) O6 0.0190(8) 0.0425(12) 0.0305(10) 0.0133(8) 0.0023(7) -0.0026(8) O7 0.0262(10) 0.0622(16) 0.0367(12) 0.0195(11) 0.0004(9) 0.0045(10) O8 0.0238(10) 0.089(2) 0.0299(10) 0.0190(12) 0.0091(9) -0.0023(12) O9 0.0220(8) 0.0212(8) 0.0291(9) 0.0012(7) -0.0063(7) 0.0008(6) O10 0.0234(9) 0.0267(10) 0.0511(13) 0.0057(9) -0.0139(9) 0.0004(8) O11 0.0295(11) 0.0285(11) 0.0748(18) -0.0180(11) -0.0079(11) 0.0014(9) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag Eu1 O3 2.451(2) . ? Eu1 O9 2.4640(19) . ? Eu1 O4 2.480(2) . ? Eu1 O10 2.505(2) . ? Eu1 O6 2.509(2) . ? Eu1 N1 2.526(2) . ? Eu1 O7 2.533(2) . ? Eu1 N2 2.534(2) . ? Eu1 O1 2.545(2) . ? Eu1 N3 2.585(2) . ? Eu1 N5 2.881(3) . ? Eu1 N7 2.909(2) . ? C1 N1 1.345(3) . ? C1 C2 1.387(4) . ? C1 H1 0.9500 . ? C2 C3 1.377(5) . ? C2 H2 0.9500 . ? C3 C4 1.388(4) . ? C3 H3 0.9500 . ? C4 C5 1.391(4) . ? C4 H4 0.9500 . ? C5 N1 1.347(3) . ? C5 C6 1.479(3) . ? C6 N2 1.349(3) . ? C6 C7 1.395(4) . ? C7 C8 1.376(4) . ? C7 H7 0.9500 . ? C8 C9 1.386(4) . ? C8 H8 0.9500 . ? C9 C10 1.385(3) . ? C9 H9 0.9500 . ? C10 N2 1.352(3) . ? C10 C11 1.481(3) . ? C11 N3 1.337(3) . ? C11 C12 1.398(3) . ? C12 C13 1.383(4) . ? C12 H12 0.9500 . ? C13 C14 1.385(4) . ? C13 H13 0.9500 . ? C14 C15 1.375(4) . ? C14 H14 0.9500 . ? C15 N3 1.326(3) . ? C15 N4 1.477(4) . ? N4 O2 1.210(3) . ? N4 O1 1.238(3) . ? N5 O5 1.207(4) . ? N5 O4 1.274(3) . ? N5 O3 1.289(3) . ? N6 O8 1.224(3) . ? N6 O6 1.240(3) . ? N6 O7 1.277(3) . ? N7 O11 1.218(3) . ? N7 O10 1.266(3) . ? N7 O9 1.269(3) . ? 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 Eu1 O9 134.70(7) . . ? O3 Eu1 O4 52.19(7) . . ? O9 Eu1 O4 144.42(7) . . ? O3 Eu1 O10 162.14(9) . . ? O9 Eu1 O10 51.09(6) . . ? O4 Eu1 O10 136.60(7) . . ? O3 Eu1 O6 67.96(7) . . ? O9 Eu1 O6 70.87(7) . . ? O4 Eu1 O6 116.98(7) . . ? O10 Eu1 O6 106.41(8) . . ? O3 Eu1 N1 78.84(9) . . ? O9 Eu1 N1 71.36(7) . . ? O4 Eu1 N1 78.23(8) . . ? O10 Eu1 N1 116.43(8) . . ? O6 Eu1 N1 72.37(7) . . ? O3 Eu1 O7 86.75(9) . . ? O9 Eu1 O7 81.05(8) . . ? O4 Eu1 O7 131.96(8) . . ? O10 Eu1 O7 77.35(9) . . ? O6 Eu1 O7 50.05(7) . . ? N1 Eu1 O7 121.70(7) . . ? O3 Eu1 N2 120.80(7) . . ? O9 Eu1 N2 75.25(7) . . ? O4 Eu1 N2 75.18(7) . . ? O10 Eu1 N2 76.04(8) . . ? O6 Eu1 N2 131.38(7) . . ? N1 Eu1 N2 64.27(7) . . ? O7 Eu1 N2 151.88(8) . . ? O3 Eu1 O1 75.75(9) . . ? O9 Eu1 O1 134.52(8) . . ? O4 Eu1 O1 79.06(9) . . ? O10 Eu1 O1 90.21(8) . . ? O6 Eu1 O1 105.75(7) . . ? N1 Eu1 O1 152.99(8) . . ? O7 Eu1 O1 65.96(8) . . ? N2 Eu1 O1 122.86(8) . . ? O3 Eu1 N3 114.30(7) . . ? O9 Eu1 N3 110.60(6) . . ? O4 Eu1 N3 72.07(7) . . ? O10 Eu1 N3 66.11(7) . . ? O6 Eu1 N3 163.35(7) . . ? N1 Eu1 N3 124.17(7) . . ? O7 Eu1 N3 113.33(7) . . ? N2 Eu1 N3 62.98(7) . . ? O1 Eu1 N3 60.79(7) . . ? O3 Eu1 N5 26.44(7) . . ? O9 Eu1 N5 144.31(8) . . ? O4 Eu1 N5 26.16(7) . . ? O10 Eu1 N5 161.24(7) . . ? O6 Eu1 N5 91.50(7) . . ? N1 Eu1 N5 73.80(8) . . ? O7 Eu1 N5 111.65(9) . . ? N2 Eu1 N5 96.46(7) . . ? O1 Eu1 N5 79.37(9) . . ? N3 Eu1 N5 95.15(7) . . ? O3 Eu1 N7 158.21(7) . . ? O9 Eu1 N7 25.64(6) . . ? O4 Eu1 N7 146.05(7) . . ? O10 Eu1 N7 25.69(7) . . ? O6 Eu1 N7 90.38(7) . . ? N1 Eu1 N7 92.78(7) . . ? O7 Eu1 N7 80.60(9) . . ? N2 Eu1 N7 71.47(7) . . ? O1 Eu1 N7 114.22(8) . . ? N3 Eu1 N7 87.10(7) . . ? N5 Eu1 N7 165.15(8) . . ? N1 C1 C2 123.2(3) . . ? N1 C1 H1 118.4 . . ? C2 C1 H1 118.4 . . ? C3 C2 C1 118.7(3) . . ? C3 C2 H2 120.7 . . ? C1 C2 H2 120.7 . . ? C2 C3 C4 118.9(3) . . ? C2 C3 H3 120.6 . . ? C4 C3 H3 120.6 . . ? C3 C4 C5 119.2(3) . . ? C3 C4 H4 120.4 . . ? C5 C4 H4 120.4 . . ? N1 C5 C4 122.1(2) . . ? N1 C5 C6 116.6(2) . . ? C4 C5 C6 121.3(2) . . ? N2 C6 C7 121.5(2) . . ? N2 C6 C5 116.7(2) . . ? C7 C6 C5 121.7(2) . . ? C8 C7 C6 119.2(3) . . ? C8 C7 H7 120.4 . . ? C6 C7 H7 120.4 . . ? C7 C8 C9 119.5(2) . . ? C7 C8 H8 120.2 . . ? C9 C8 H8 120.2 . . ? C10 C9 C8 118.7(2) . . ? C10 C9 H9 120.7 . . ? C8 C9 H9 120.7 . . ? N2 C10 C9 122.2(2) . . ? N2 C10 C11 116.0(2) . . ? C9 C10 C11 121.8(2) . . ? N3 C11 C12 121.1(2) . . ? N3 C11 C10 116.6(2) . . ? C12 C11 C10 122.3(2) . . ? C13 C12 C11 119.7(2) . . ? C13 C12 H12 120.2 . . ? C11 C12 H12 120.2 . . ? C12 C13 C14 119.4(2) . . ? C12 C13 H13 120.3 . . ? C14 C13 H13 120.3 . . ? C15 C14 C13 116.1(2) . . ? C15 C14 H14 122.0 . . ? C13 C14 H14 122.0 . . ? N3 C15 C14 126.3(3) . . ? N3 C15 N4 114.0(2) . . ? C14 C15 N4 119.6(2) . . ? C1 N1 C5 117.8(2) . . ? C1 N1 Eu1 121.55(19) . . ? C5 N1 Eu1 120.11(16) . . ? C6 N2 C10 118.7(2) . . ? C6 N2 Eu1 118.91(16) . . ? C10 N2 Eu1 121.10(16) . . ? C15 N3 C11 117.3(2) . . ? C15 N3 Eu1 122.05(17) . . ? C11 N3 Eu1 120.25(15) . . ? O2 N4 O1 123.4(3) . . ? O2 N4 C15 118.9(2) . . ? O1 N4 C15 117.7(2) . . ? O5 N5 O4 122.9(3) . . ? O5 N5 O3 121.5(3) . . ? O4 N5 O3 115.6(3) . . ? O5 N5 Eu1 167.0(3) . . ? O4 N5 Eu1 59.09(15) . . ? O3 N5 Eu1 57.84(14) . . ? O8 N6 O6 121.9(3) . . ? O8 N6 O7 122.1(3) . . ? O6 N6 O7 115.9(2) . . ? O8 N6 Eu1 177.1(3) . . ? O6 N6 Eu1 57.50(13) . . ? O7 N6 Eu1 58.82(14) . . ? O11 N7 O10 124.1(2) . . ? O11 N7 O9 120.5(2) . . ? O10 N7 O9 115.4(2) . . ? O11 N7 Eu1 170.6(2) . . ? O10 N7 Eu1 59.05(14) . . ? O9 N7 Eu1 57.20(12) . . ? N4 O1 Eu1 124.84(18) . . ? N5 O3 Eu1 95.72(16) . . ? N5 O4 Eu1 94.75(17) . . ? N6 O6 Eu1 97.86(16) . . ? N6 O7 Eu1 95.63(16) . . ? N7 O9 Eu1 97.16(15) . . ? N7 O10 Eu1 95.27(15) . . ? _diffrn_measured_fraction_theta_max 0.999 _diffrn_reflns_theta_full 33.19 _diffrn_measured_fraction_theta_full 0.999 _refine_diff_density_max 2.140 _refine_diff_density_min -1.071 _refine_diff_density_rms 0.141 data_pbca-o42207-trial2 _database_code_depnum_ccdc_archive 'CCDC 886731' #TrackingRef 'terpyNO2TbNO3.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C15 H10 N7 O11 Tb' _chemical_formula_weight 623.22 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 Orthorhombic _symmetry_space_group_name_H-M Pbca 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' '-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 15.125(3) _cell_length_b 13.776(3) _cell_length_c 18.716(4) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 3899.8(13) _cell_formula_units_Z 8 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 8151 _cell_measurement_theta_min 2.1675 _cell_measurement_theta_max 28.23 _exptl_crystal_description plates _exptl_crystal_colour colorless _exptl_crystal_size_max 0.20 _exptl_crystal_size_mid 0.14 _exptl_crystal_size_min 0.12 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 2.123 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 2416 _exptl_absorpt_coefficient_mu 3.708 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.5243 _exptl_absorpt_correction_T_max 0.6646 _exptl_absorpt_process_details 'SADABS SHELXL-97 (Sheldrick, 1997)' _exptl_special_details ; ? ; _diffrn_ambient_temperature 100(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'APEX CCD detector' _diffrn_measurement_method 'Phi and omega scans' _diffrn_detector_area_resol_mean 8.3 _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% 0.001 _diffrn_reflns_number 40763 _diffrn_reflns_av_R_equivalents 0.0413 _diffrn_reflns_av_sigmaI/netI 0.0228 _diffrn_reflns_limit_h_min -20 _diffrn_reflns_limit_h_max 20 _diffrn_reflns_limit_k_min -18 _diffrn_reflns_limit_k_max 18 _diffrn_reflns_limit_l_min -24 _diffrn_reflns_limit_l_max 24 _diffrn_reflns_theta_min 2.18 _diffrn_reflns_theta_max 28.26 _reflns_number_total 4810 _reflns_number_gt 4302 _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^)+(0.1000P)^2^+0.0278P] 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 4810 _refine_ls_number_parameters 347 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0311 _refine_ls_R_factor_gt 0.0273 _refine_ls_wR_factor_ref 0.1025 _refine_ls_wR_factor_gt 0.0959 _refine_ls_goodness_of_fit_ref 0.876 _refine_ls_restrained_S_all 0.876 _refine_ls_shift/su_max 0.006 _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 Tb1 Tb 1.027050(8) 0.321279(9) 0.388978(7) 0.01531(9) Uani 1 1 d . . . C1 C 1.1798(2) 0.17938(19) 0.3043(2) 0.0257(7) Uani 1 1 d . . . H1 H 1.201(3) 0.169(2) 0.352(2) 0.028(10) Uiso 1 1 d . . . C2 C 1.23062(19) 0.1395(2) 0.24998(18) 0.0302(7) Uani 1 1 d . . . H2 H 1.285(3) 0.096(4) 0.263(3) 0.073(16) Uiso 1 1 d . . . C3 C 1.2021(2) 0.1487(2) 0.18061(18) 0.0296(6) Uani 1 1 d . . . H3 H 1.226(2) 0.130(3) 0.147(2) 0.030(10) Uiso 1 1 d . . . C4 C 1.1233(2) 0.1974(2) 0.16695(17) 0.0259(6) Uani 1 1 d . . . H4 H 1.098(4) 0.195(4) 0.121(2) 0.046(14) Uiso 1 1 d . . . C5 C 1.07752(17) 0.23896(18) 0.22353(14) 0.0188(5) Uani 1 1 d . . . C6 C 0.99412(18) 0.29365(19) 0.21197(14) 0.0174(5) Uani 1 1 d . . . C7 C 0.9639(2) 0.3166(2) 0.1442(2) 0.0237(7) Uani 1 1 d . . . H7 H 0.999(3) 0.303(3) 0.1005(19) 0.018(8) Uiso 1 1 d . . . C8 C 0.88377(19) 0.3629(2) 0.13636(16) 0.0254(6) Uani 1 1 d . . . H8 H 0.861(3) 0.375(3) 0.091(2) 0.030(9) Uiso 1 1 d . . . C9 C 0.83403(18) 0.3843(2) 0.19664(16) 0.0225(6) Uani 1 1 d . . . H9 H 0.772(2) 0.406(3) 0.1979(19) 0.025(8) Uiso 1 1 d . . . C10 C 0.86840(17) 0.36206(18) 0.26332(14) 0.0177(5) Uani 1 1 d . . . C11 C 0.81875(16) 0.37964(18) 0.32993(14) 0.0176(5) Uani 1 1 d . . . C12 C 0.73054(18) 0.4111(2) 0.32997(17) 0.0229(5) Uani 1 1 d . . . H12 H 0.704(2) 0.431(2) 0.2854(18) 0.021(8) Uiso 1 1 d . . . C13 C 0.6871(2) 0.4228(2) 0.39440(16) 0.0267(6) Uani 1 1 d . . . H13 H 0.631(3) 0.437(3) 0.3982(18) 0.032(10) Uiso 1 1 d . . . C14 C 0.73062(19) 0.4030(2) 0.45761(17) 0.0257(6) Uani 1 1 d . . . H14 H 0.708(3) 0.412(3) 0.502(2) 0.037(10) Uiso 1 1 d . . . C15 C 0.81748(18) 0.3735(2) 0.45128(15) 0.0219(5) Uani 1 1 d . . . N1 N 1.10441(14) 0.22930(16) 0.29201(12) 0.0193(4) Uani 1 1 d . . . N2 N 0.94842(18) 0.31945(14) 0.27093(14) 0.0161(5) Uani 1 1 d . . . N3 N 0.86180(16) 0.36105(18) 0.39094(11) 0.0182(5) Uani 1 1 d . . . N4 N 0.87042(17) 0.3554(2) 0.51584(14) 0.0277(5) Uani 1 1 d . . . N5 N 1.18340(15) 0.36919(19) 0.47329(13) 0.0247(5) Uani 1 1 d . . . N6 N 1.00221(18) 0.12041(18) 0.42177(16) 0.0302(6) Uani 1 1 d . . . N7 N 1.05388(16) 0.50740(16) 0.32046(13) 0.0216(5) Uani 1 1 d . . . O1 O 0.94791(18) 0.32932(16) 0.50754(13) 0.0315(5) Uani 1 1 d . . . O2 O 0.83622(15) 0.36744(19) 0.57436(11) 0.0344(5) Uani 1 1 d . . . O3 O 1.18634(15) 0.31244(15) 0.42143(13) 0.0274(5) Uani 1 1 d . . . O4 O 1.11004(14) 0.41180(18) 0.48395(12) 0.0340(5) Uani 1 1 d . . . O5 O 1.24890(15) 0.3851(2) 0.51058(12) 0.0410(6) Uani 1 1 d . . . O6 O 1.06423(16) 0.17075(14) 0.45038(14) 0.0321(5) Uani 1 1 d . . . O7 O 0.9438(2) 0.16829(16) 0.38775(12) 0.0275(5) Uani 1 1 d . . . O8 O 1.00260(19) 0.03208(17) 0.42493(19) 0.0484(7) Uani 1 1 d . . . O9 O 1.10894(13) 0.43743(14) 0.31589(11) 0.0219(4) Uani 1 1 d . . . O10 O 0.99219(15) 0.49506(15) 0.36572(14) 0.0280(5) Uani 1 1 d . . . O11 O 1.06152(15) 0.57916(16) 0.28339(14) 0.0368(5) Uani 1 1 d . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 Tb1 0.01229(12) 0.01797(12) 0.01568(12) 0.00019(4) -0.00055(4) -0.00012(4) C1 0.0181(15) 0.0253(16) 0.0337(17) -0.0092(11) -0.0046(13) 0.0057(10) C2 0.0242(15) 0.0213(16) 0.045(2) -0.0069(12) 0.0033(14) 0.0059(11) C3 0.0334(17) 0.0208(14) 0.0346(17) -0.0010(13) 0.0135(13) 0.0057(12) C4 0.0309(16) 0.0201(12) 0.0266(15) 0.0007(11) 0.0060(12) 0.0012(11) C5 0.0200(12) 0.0145(11) 0.0219(12) -0.0024(9) 0.0012(10) -0.0030(9) C6 0.0179(12) 0.0165(11) 0.0177(12) -0.0017(10) -0.0021(10) -0.0021(10) C7 0.0233(15) 0.0292(17) 0.0185(15) -0.0017(11) -0.0001(11) -0.0041(10) C8 0.0229(14) 0.0305(15) 0.0227(14) 0.0022(12) -0.0080(11) -0.0028(11) C9 0.0175(13) 0.0265(14) 0.0236(13) 0.0029(11) -0.0062(10) 0.0002(10) C10 0.0151(11) 0.0159(12) 0.0219(13) -0.0005(9) -0.0013(9) -0.0033(9) C11 0.0140(11) 0.0154(11) 0.0234(13) 0.0018(10) -0.0001(9) -0.0020(9) C12 0.0154(12) 0.0195(12) 0.0339(15) -0.0010(11) -0.0024(11) 0.0000(10) C13 0.0136(14) 0.0293(15) 0.0372(17) -0.0062(11) 0.0019(10) 0.0005(11) C14 0.0192(13) 0.0259(14) 0.0320(16) -0.0035(12) 0.0086(11) -0.0033(11) C15 0.0193(13) 0.0243(13) 0.0220(13) 0.0000(11) 0.0058(10) -0.0029(10) N1 0.0166(10) 0.0165(10) 0.0247(11) -0.0055(9) -0.0035(8) 0.0023(8) N2 0.0132(10) 0.0153(11) 0.0199(12) 0.0011(7) -0.0005(10) -0.0029(7) N3 0.0166(11) 0.0180(11) 0.0202(12) 0.0026(7) 0.0028(7) -0.0025(9) N4 0.0251(12) 0.0351(14) 0.0229(12) 0.0027(10) 0.0066(10) -0.0041(11) N5 0.0186(11) 0.0382(14) 0.0174(11) -0.0040(10) -0.0001(9) -0.0022(10) N6 0.0250(12) 0.0227(12) 0.0428(16) 0.0053(12) -0.0049(12) -0.0032(10) N7 0.0170(11) 0.0177(11) 0.0300(13) -0.0009(9) 0.0018(9) -0.0035(9) O1 0.0235(11) 0.0479(15) 0.0230(12) 0.0068(9) 0.0036(10) 0.0041(9) O2 0.0322(12) 0.0522(14) 0.0187(10) 0.0007(10) 0.0108(8) -0.0023(10) O3 0.0206(11) 0.0336(12) 0.0278(12) -0.0105(8) -0.0054(9) -0.0028(8) O4 0.0258(11) 0.0471(14) 0.0289(11) -0.0137(10) 0.0030(9) -0.0012(9) O5 0.0241(11) 0.0735(19) 0.0253(11) -0.0131(12) -0.0067(9) -0.0077(11) O6 0.0236(12) 0.0276(11) 0.0452(15) 0.0120(9) -0.0111(10) -0.0061(8) O7 0.0199(13) 0.0233(11) 0.0392(16) 0.0064(8) -0.0091(8) -0.0017(9) O8 0.0377(13) 0.0237(12) 0.084(2) 0.0157(13) -0.0120(15) -0.0056(11) O9 0.0215(9) 0.0192(9) 0.0250(10) -0.0020(8) 0.0045(8) 0.0007(7) O10 0.0212(10) 0.0232(10) 0.0396(13) -0.0051(10) 0.0112(10) 0.0003(8) O11 0.0282(12) 0.0272(11) 0.0548(15) 0.0157(10) 0.0057(10) 0.0015(9) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag Tb1 O6 2.437(2) . ? Tb1 O9 2.442(2) . ? Tb1 O7 2.455(2) . ? Tb1 O3 2.488(2) . ? Tb1 O10 2.490(2) . ? Tb1 N1 2.504(2) . ? Tb1 O4 2.508(2) . ? Tb1 N2 2.509(3) . ? Tb1 O1 2.524(3) . ? Tb1 N3 2.559(2) . ? C1 N1 1.351(4) . ? C1 C2 1.388(4) . ? C1 H1 0.95(4) . ? C2 C3 1.374(5) . ? C2 H2 1.04(5) . ? C3 C4 1.392(4) . ? C3 H3 0.77(4) . ? C4 C5 1.389(4) . ? C4 H4 0.94(5) . ? C5 N1 1.351(3) . ? C5 C6 1.485(4) . ? C6 N2 1.350(4) . ? C6 C7 1.385(4) . ? C7 C8 1.377(4) . ? C7 H7 1.00(4) . ? C8 C9 1.388(4) . ? C8 H8 0.93(4) . ? C9 C10 1.386(4) . ? C9 H9 0.98(4) . ? C10 N2 1.353(4) . ? C10 C11 1.475(4) . ? C11 N3 1.339(3) . ? C11 C12 1.403(4) . ? C12 C13 1.383(4) . ? C12 H12 0.96(3) . ? C13 C14 1.381(4) . ? C13 H13 0.88(4) . ? C14 C15 1.380(4) . ? C14 H14 0.92(4) . ? C15 N3 1.325(3) . ? C15 N4 1.471(4) . ? N4 O2 1.223(3) . ? N4 O1 1.236(4) . ? N5 O5 1.232(3) . ? N5 O3 1.247(3) . ? N5 O4 1.271(3) . ? N6 O8 1.218(3) . ? N6 O7 1.273(4) . ? N6 O6 1.284(3) . ? N7 O11 1.213(3) . ? N7 O10 1.272(3) . ? N7 O9 1.277(3) . ? 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 O6 Tb1 O9 134.80(7) . . ? O6 Tb1 O7 52.57(8) . . ? O9 Tb1 O7 144.81(7) . . ? O6 Tb1 O3 67.65(8) . . ? O9 Tb1 O3 71.20(7) . . ? O7 Tb1 O3 117.19(8) . . ? O6 Tb1 O10 161.74(9) . . ? O9 Tb1 O10 51.65(7) . . ? O7 Tb1 O10 135.65(8) . . ? O3 Tb1 O10 107.15(7) . . ? O6 Tb1 N1 78.66(8) . . ? O9 Tb1 N1 71.86(7) . . ? O7 Tb1 N1 78.37(8) . . ? O3 Tb1 N1 72.52(7) . . ? O10 Tb1 N1 117.31(8) . . ? O6 Tb1 O4 88.48(8) . . ? O9 Tb1 O4 79.48(7) . . ? O7 Tb1 O4 133.64(7) . . ? O3 Tb1 O4 50.70(7) . . ? O10 Tb1 O4 75.63(8) . . ? N1 Tb1 O4 122.11(7) . . ? O6 Tb1 N2 121.07(7) . . ? O9 Tb1 N2 75.75(7) . . ? O7 Tb1 N2 74.93(7) . . ? O3 Tb1 N2 132.34(8) . . ? O10 Tb1 N2 75.84(7) . . ? N1 Tb1 N2 65.05(8) . . ? O4 Tb1 N2 150.02(7) . . ? O6 Tb1 O1 74.46(8) . . ? O9 Tb1 O1 134.76(7) . . ? O7 Tb1 O1 78.62(8) . . ? O3 Tb1 O1 104.29(9) . . ? O10 Tb1 O1 90.64(7) . . ? N1 Tb1 O1 151.79(7) . . ? O4 Tb1 O1 65.94(8) . . ? N2 Tb1 O1 123.36(11) . . ? O6 Tb1 N3 113.63(8) . . ? O9 Tb1 N3 111.29(7) . . ? O7 Tb1 N3 71.52(9) . . ? O3 Tb1 N3 162.35(7) . . ? O10 Tb1 N3 65.78(7) . . ? N1 Tb1 N3 125.11(7) . . ? O4 Tb1 N3 111.85(7) . . ? N2 Tb1 N3 63.37(8) . . ? O1 Tb1 N3 60.97(8) . . ? N1 C1 C2 123.0(3) . . ? N1 C1 H1 121(2) . . ? C2 C1 H1 116(2) . . ? C3 C2 C1 118.8(3) . . ? C3 C2 H2 121(3) . . ? C1 C2 H2 120(3) . . ? C2 C3 C4 119.1(3) . . ? C2 C3 H3 126(3) . . ? C4 C3 H3 114(3) . . ? C5 C4 C3 119.1(3) . . ? C5 C4 H4 120(3) . . ? C3 C4 H4 120(3) . . ? N1 C5 C4 122.2(3) . . ? N1 C5 C6 116.3(2) . . ? C4 C5 C6 121.4(3) . . ? N2 C6 C7 121.3(3) . . ? N2 C6 C5 116.7(2) . . ? C7 C6 C5 122.0(2) . . ? C8 C7 C6 119.6(3) . . ? C8 C7 H7 118(2) . . ? C6 C7 H7 122(2) . . ? C7 C8 C9 119.2(3) . . ? C7 C8 H8 120(2) . . ? C9 C8 H8 120(2) . . ? C10 C9 C8 118.8(3) . . ? C10 C9 H9 114(2) . . ? C8 C9 H9 127(2) . . ? N2 C10 C9 121.7(3) . . ? N2 C10 C11 116.0(2) . . ? C9 C10 C11 122.3(2) . . ? N3 C11 C12 121.4(3) . . ? N3 C11 C10 116.2(2) . . ? C12 C11 C10 122.4(2) . . ? C13 C12 C11 119.2(3) . . ? C13 C12 H12 122(2) . . ? C11 C12 H12 119(2) . . ? C14 C13 C12 119.9(3) . . ? C14 C13 H13 116(2) . . ? C12 C13 H13 124(2) . . ? C15 C14 C13 116.0(3) . . ? C15 C14 H14 119(3) . . ? C13 C14 H14 125(3) . . ? N3 C15 C14 126.4(3) . . ? N3 C15 N4 113.8(2) . . ? C14 C15 N4 119.8(3) . . ? C5 N1 C1 117.7(2) . . ? C5 N1 Tb1 119.81(16) . . ? C1 N1 Tb1 121.9(2) . . ? C6 N2 C10 119.1(2) . . ? C6 N2 Tb1 118.67(19) . . ? C10 N2 Tb1 120.83(18) . . ? C15 N3 C11 117.1(3) . . ? C15 N3 Tb1 122.29(18) . . ? C11 N3 Tb1 120.24(17) . . ? O2 N4 O1 123.6(3) . . ? O2 N4 C15 118.9(2) . . ? O1 N4 C15 117.5(2) . . ? O5 N5 O3 121.6(3) . . ? O5 N5 O4 122.1(3) . . ? O3 N5 O4 116.3(2) . . ? O8 N6 O7 123.0(3) . . ? O8 N6 O6 121.1(3) . . ? O7 N6 O6 115.8(2) . . ? O11 N7 O10 124.0(2) . . ? O11 N7 O9 121.0(2) . . ? O10 N7 O9 115.0(2) . . ? N4 O1 Tb1 125.0(2) . . ? N5 O3 Tb1 97.16(17) . . ? N5 O4 Tb1 95.51(16) . . ? N6 O6 Tb1 95.41(16) . . ? N6 O7 Tb1 94.82(18) . . ? N7 O9 Tb1 97.26(15) . . ? N7 O10 Tb1 95.14(15) . . ? _diffrn_measured_fraction_theta_max 0.998 _diffrn_reflns_theta_full 28.26 _diffrn_measured_fraction_theta_full 0.998 _refine_diff_density_max 1.599 _refine_diff_density_min -0.605 _refine_diff_density_rms 0.131 data_aa0016b_nomerge_p1_040507 _database_code_depnum_ccdc_archive 'CCDC 886732' #TrackingRef 'tpaNO3EuCF3SO3.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C44 H42 Eu2 F12 N12 O18 S4' _chemical_formula_weight 1687.06 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Eu Eu -0.1578 3.6682 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' F F 0.0171 0.0103 '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' S S 0.1246 0.1234 '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 11.067(2) _cell_length_b 11.633(2) _cell_length_c 12.772(3) _cell_angle_alpha 110.94(3) _cell_angle_beta 97.49(3) _cell_angle_gamma 91.42(3) _cell_volume 1518.1(5) _cell_formula_units_Z 1 _cell_measurement_temperature 96(2) _cell_measurement_reflns_used 5100 _cell_measurement_theta_min 2.68 _cell_measurement_theta_max 28.37 _exptl_crystal_description parallelepiped _exptl_crystal_colour colorless _exptl_crystal_size_max 0.20 _exptl_crystal_size_mid 0.18 _exptl_crystal_size_min 0.08 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.845 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 832 _exptl_absorpt_coefficient_mu 2.299 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.6564 _exptl_absorpt_correction_T_max 0.8375 _exptl_absorpt_process_details 'SADABS SHELXL-97 (Sheldrick, 1997)' _exptl_special_details ; ? ; _diffrn_ambient_temperature 100(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'APEX CCD detector' _diffrn_measurement_method 'Phi and omega scans' _diffrn_detector_area_resol_mean 8.3 _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% 0.001 _diffrn_reflns_number 16104 _diffrn_reflns_av_R_equivalents 0.0189 _diffrn_reflns_av_sigmaI/netI 0.0280 _diffrn_reflns_limit_h_min -14 _diffrn_reflns_limit_h_max 13 _diffrn_reflns_limit_k_min -15 _diffrn_reflns_limit_k_max 15 _diffrn_reflns_limit_l_min -16 _diffrn_reflns_limit_l_max 16 _diffrn_reflns_theta_min 1.73 _diffrn_reflns_theta_max 27.50 _reflns_number_total 6942 _reflns_number_gt 6666 _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^)+(0.0284P)^2^+1.1033P] 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 6942 _refine_ls_number_parameters 427 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0234 _refine_ls_R_factor_gt 0.0223 _refine_ls_wR_factor_ref 0.0544 _refine_ls_wR_factor_gt 0.0538 _refine_ls_goodness_of_fit_ref 1.025 _refine_ls_restrained_S_all 1.025 _refine_ls_shift/su_max 0.003 _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 Eu1 Eu 0.596765(9) 0.107205(9) 0.137549(8) 0.01072(4) Uani 1 1 d . . . S3 S 0.36119(5) 0.34262(5) 0.21919(5) 0.01531(11) Uani 1 1 d . . . S6 S 0.74225(5) -0.11615(5) 0.25293(5) 0.01513(11) Uani 1 1 d . . . F1 F 0.34358(15) 0.38267(15) 0.43172(12) 0.0328(4) Uani 1 1 d . . . F2 F 0.17842(14) 0.40552(15) 0.33448(14) 0.0334(4) Uani 1 1 d . . . F3 F 0.23357(16) 0.22286(14) 0.31243(15) 0.0363(4) Uani 1 1 d . . . F6 F 0.80500(16) 0.03270(15) 0.46478(13) 0.0353(4) Uani 1 1 d . . . F7 F 0.85807(18) -0.15172(16) 0.42923(14) 0.0403(4) Uani 1 1 d . . . F8 F 0.95607(15) -0.0275(2) 0.37351(16) 0.0460(5) Uani 1 1 d . . . O1 O 0.34052(16) -0.04476(17) 0.32205(15) 0.0273(4) Uani 1 1 d . . . O2 O 0.43743(14) -0.00961(14) 0.19894(13) 0.0169(3) Uani 1 1 d . . . O5 O 0.42806(14) 0.08301(13) 0.00141(13) 0.0144(3) Uani 1 1 d . . . O7 O 0.80015(16) -0.21797(15) 0.18225(15) 0.0234(4) Uani 1 1 d . . . O8 O 0.74424(14) -0.00837(14) 0.22014(13) 0.0175(3) Uani 1 1 d . . . O9 O 0.62730(16) -0.14463(16) 0.28321(15) 0.0238(4) Uani 1 1 d . . . O13 O 0.45807(14) 0.26401(14) 0.23185(13) 0.0180(3) Uani 1 1 d . . . O14 O 0.27656(15) 0.28985(16) 0.11602(14) 0.0234(4) Uani 1 1 d . . . O17 O 0.40180(17) 0.47029(15) 0.25185(15) 0.0252(4) Uani 1 1 d . . . N1 N 0.62762(17) 0.29957(16) 0.08478(16) 0.0152(4) Uani 1 1 d . . . N2 N 0.58925(17) 0.15608(16) 0.35485(15) 0.0144(4) Uani 1 1 d . . . N3 N 0.80019(17) 0.11101(17) 0.06021(16) 0.0156(4) Uani 1 1 d . . . N7 N 0.76480(17) 0.28020(17) 0.28200(15) 0.0144(4) Uani 1 1 d . . . N9 N 0.41894(17) 0.01172(17) 0.29703(16) 0.0168(4) Uani 1 1 d . . . C1 C 0.6636(2) 0.2467(2) 0.43427(18) 0.0160(4) Uani 1 1 d . . . C2 C 0.4963(2) 0.1121(2) 0.38914(19) 0.0161(4) Uani 1 1 d . . . C3 C 0.4668(2) 0.1509(2) 0.4969(2) 0.0207(5) Uani 1 1 d . . . H3 H 0.3995 0.1135 0.5153 0.025 Uiso 1 1 calc R . . C4 C 0.5418(2) 0.2484(2) 0.5774(2) 0.0244(5) Uani 1 1 d . . . H4 H 0.5252 0.2818 0.6532 0.029 Uiso 1 1 calc R . . C5 C 0.6410(2) 0.2965(2) 0.54644(19) 0.0204(5) Uani 1 1 d . . . H5 H 0.6933 0.3628 0.6009 0.024 Uiso 1 1 calc R . . C6 C 0.8885(2) 0.2012(2) 0.1195(2) 0.0169(4) Uani 1 1 d . . . C7 C 0.9875(2) 0.2261(2) 0.0725(2) 0.0227(5) Uani 1 1 d . . . H7 H 1.0465 0.2924 0.1155 0.027 Uiso 1 1 calc R . . C8 C 0.9995(2) 0.1534(3) -0.0374(2) 0.0268(5) Uani 1 1 d . . . H8 H 1.0675 0.1679 -0.0705 0.032 Uiso 1 1 calc R . . C9 C 0.9108(2) 0.0594(2) -0.0981(2) 0.0244(5) Uani 1 1 d . . . H9 H 0.9169 0.0077 -0.1737 0.029 Uiso 1 1 calc R . . C14 C 0.8125(2) 0.0417(2) -0.04679(19) 0.0185(4) Uani 1 1 d . . . H14 H 0.7511 -0.0224 -0.0893 0.022 Uiso 1 1 calc R . . C15 C 0.6893(2) 0.4017(2) 0.16419(19) 0.0164(4) Uani 1 1 d . . . C16 C 0.7183(2) 0.5058(2) 0.1411(2) 0.0217(5) Uani 1 1 d . . . H16 H 0.7620 0.5763 0.1986 0.026 Uiso 1 1 calc R . . C17 C 0.6828(2) 0.5058(2) 0.0326(2) 0.0251(5) Uani 1 1 d . . . H17 H 0.7019 0.5760 0.0147 0.030 Uiso 1 1 calc R . . C18 C 0.5932(2) 0.3008(2) -0.0192(2) 0.0185(4) Uani 1 1 d . . . H18 H 0.5493 0.2296 -0.0754 0.022 Uiso 1 1 calc R . . C27 C 0.6192(2) 0.4020(2) -0.0484(2) 0.0229(5) Uani 1 1 d . . . H27 H 0.5936 0.3996 -0.1231 0.028 Uiso 1 1 calc R . . C29 C 0.7788(2) 0.2847(2) 0.40060(19) 0.0175(4) Uani 1 1 d . . . H29A H 0.8073 0.3698 0.4523 0.021 Uiso 1 1 calc R . . H29B H 0.8426 0.2298 0.4106 0.021 Uiso 1 1 calc R . . C31 C 0.7205(2) 0.39996(19) 0.28193(19) 0.0170(4) Uani 1 1 d . . . H31A H 0.7845 0.4670 0.3258 0.020 Uiso 1 1 calc R . . H31B H 0.6471 0.4163 0.3202 0.020 Uiso 1 1 calc R . . C33 C 0.2749(2) 0.3384(2) 0.3304(2) 0.0220(5) Uani 1 1 d . . . C36 C 0.8459(2) -0.0628(2) 0.3873(2) 0.0251(5) Uani 1 1 d . . . C38 C 0.8871(2) 0.2645(2) 0.2446(2) 0.0190(5) Uani 1 1 d . . . H38A H 0.9337 0.2168 0.2845 0.023 Uiso 1 1 calc R . . H38B H 0.9310 0.3471 0.2695 0.023 Uiso 1 1 calc R . . N11 N 0.0051(3) 0.6034(3) 0.3534(3) 0.0507(7) Uani 1 1 d . A . C41 C 0.0433(3) 0.6318(4) 0.2889(4) 0.0530(9) Uani 1 1 d . . . C42 C 0.0959(14) 0.696(2) 0.2288(19) 0.060(5) Uani 0.44(5) 1 d P A 1 H42A H 0.0326 0.7071 0.1727 0.072 Uiso 0.44(5) 1 calc PR A 1 H42B H 0.1595 0.6486 0.1901 0.072 Uiso 0.44(5) 1 calc PR A 1 H42C H 0.1320 0.7770 0.2819 0.072 Uiso 0.44(5) 1 calc PR A 1 C43 C 0.087(2) 0.641(5) 0.183(4) 0.135(11) Uani 0.56(5) 1 d P A 2 H43A H 0.1280 0.5675 0.1450 0.162 Uiso 0.56(5) 1 calc PR A 2 H43B H 0.1433 0.7147 0.2045 0.162 Uiso 0.56(5) 1 calc PR A 2 H43C H 0.0159 0.6475 0.1306 0.162 Uiso 0.56(5) 1 calc PR A 2 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 0.01158(6) 0.01038(6) 0.00963(6) 0.00284(4) 0.00221(4) -0.00064(4) S3 0.0168(3) 0.0142(2) 0.0148(3) 0.0045(2) 0.0042(2) 0.0032(2) S6 0.0166(3) 0.0160(2) 0.0143(3) 0.0068(2) 0.0038(2) 0.0009(2) F1 0.0388(9) 0.0418(9) 0.0177(7) 0.0093(7) 0.0078(7) 0.0068(7) F2 0.0245(8) 0.0389(9) 0.0379(9) 0.0108(7) 0.0153(7) 0.0145(7) F3 0.0438(10) 0.0270(8) 0.0432(10) 0.0138(7) 0.0222(8) -0.0020(7) F6 0.0519(10) 0.0310(8) 0.0172(7) 0.0036(6) -0.0013(7) 0.0094(7) F7 0.0594(11) 0.0372(9) 0.0296(9) 0.0208(8) -0.0020(8) 0.0143(8) F8 0.0230(8) 0.0729(13) 0.0390(10) 0.0214(10) -0.0065(7) -0.0088(8) O1 0.0283(10) 0.0321(10) 0.0237(9) 0.0122(8) 0.0073(7) -0.0090(8) O2 0.0201(8) 0.0174(8) 0.0127(8) 0.0045(6) 0.0041(6) -0.0014(6) O5 0.0161(7) 0.0130(7) 0.0125(7) 0.0029(6) 0.0021(6) 0.0010(6) O7 0.0311(9) 0.0168(8) 0.0247(9) 0.0075(7) 0.0126(7) 0.0038(7) O8 0.0203(8) 0.0161(7) 0.0180(8) 0.0085(6) 0.0023(6) 0.0015(6) O9 0.0213(9) 0.0290(9) 0.0259(9) 0.0140(8) 0.0095(7) 0.0001(7) O13 0.0176(8) 0.0189(8) 0.0164(8) 0.0043(6) 0.0033(6) 0.0062(6) O14 0.0220(9) 0.0262(9) 0.0187(8) 0.0052(7) 0.0003(7) 0.0049(7) O17 0.0348(10) 0.0141(8) 0.0274(9) 0.0061(7) 0.0111(8) 0.0024(7) N1 0.0170(9) 0.0117(8) 0.0164(9) 0.0045(7) 0.0033(7) 0.0002(7) N2 0.0177(9) 0.0129(8) 0.0126(9) 0.0044(7) 0.0030(7) 0.0016(7) N3 0.0141(9) 0.0174(9) 0.0166(9) 0.0077(7) 0.0026(7) 0.0006(7) N7 0.0156(9) 0.0152(9) 0.0126(9) 0.0050(7) 0.0025(7) 0.0006(7) N9 0.0185(9) 0.0173(9) 0.0164(9) 0.0078(8) 0.0043(7) -0.0002(7) C1 0.0208(11) 0.0140(10) 0.0128(10) 0.0051(8) 0.0005(8) 0.0012(8) C2 0.0188(11) 0.0150(10) 0.0147(10) 0.0057(8) 0.0022(8) 0.0012(8) C3 0.0257(12) 0.0232(11) 0.0167(11) 0.0096(9) 0.0082(9) 0.0034(9) C4 0.0350(14) 0.0244(12) 0.0148(11) 0.0065(10) 0.0081(10) 0.0046(10) C5 0.0286(12) 0.0185(11) 0.0131(11) 0.0048(9) 0.0025(9) 0.0012(9) C6 0.0139(10) 0.0183(10) 0.0204(11) 0.0091(9) 0.0033(8) 0.0023(8) C7 0.0171(11) 0.0278(12) 0.0265(13) 0.0136(10) 0.0042(9) -0.0013(9) C8 0.0208(12) 0.0380(14) 0.0284(13) 0.0176(12) 0.0115(10) 0.0028(10) C9 0.0256(12) 0.0322(13) 0.0176(12) 0.0091(10) 0.0101(10) 0.0059(10) C14 0.0179(11) 0.0214(11) 0.0173(11) 0.0077(9) 0.0038(9) 0.0026(9) C15 0.0156(10) 0.0149(10) 0.0183(11) 0.0056(9) 0.0027(8) 0.0004(8) C16 0.0249(12) 0.0141(10) 0.0249(12) 0.0073(9) -0.0004(10) -0.0037(9) C17 0.0306(13) 0.0182(11) 0.0305(14) 0.0147(10) 0.0020(11) -0.0012(10) C18 0.0225(11) 0.0154(10) 0.0175(11) 0.0059(9) 0.0025(9) 0.0007(9) C27 0.0293(13) 0.0220(12) 0.0208(12) 0.0118(10) 0.0033(10) 0.0028(10) C29 0.0199(11) 0.0178(10) 0.0134(10) 0.0055(9) -0.0007(8) -0.0039(8) C31 0.0192(11) 0.0117(10) 0.0180(11) 0.0036(8) 0.0006(9) -0.0001(8) C33 0.0217(12) 0.0214(11) 0.0232(12) 0.0068(10) 0.0081(10) 0.0047(9) C36 0.0260(13) 0.0287(13) 0.0220(12) 0.0119(10) 0.0004(10) 0.0048(10) C38 0.0128(10) 0.0214(11) 0.0203(12) 0.0049(9) 0.0022(9) -0.0021(8) N11 0.0373(15) 0.0445(16) 0.070(2) 0.0244(16) -0.0057(14) 0.0028(12) C41 0.0330(17) 0.057(2) 0.080(3) 0.042(2) -0.0019(17) 0.0090(15) C42 0.040(7) 0.090(10) 0.069(9) 0.050(7) 0.007(6) 0.017(5) C43 0.142(15) 0.18(3) 0.15(2) 0.12(2) 0.089(14) 0.064(17) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag Eu1 O5 2.2710(17) 2_655 ? Eu1 O5 2.3165(17) . ? Eu1 O13 2.4869(17) . ? Eu1 O8 2.5016(17) . ? Eu1 O2 2.5641(17) . ? Eu1 N3 2.5791(19) . ? Eu1 N1 2.5843(18) . ? Eu1 N2 2.6396(19) . ? Eu1 N7 2.679(2) . ? Eu1 Eu1 3.8292(18) 2_655 ? S3 O17 1.4342(17) . ? S3 O14 1.4360(19) . ? S3 O13 1.4563(16) . ? S3 C33 1.826(2) . ? S6 O7 1.4327(18) . ? S6 O9 1.4410(17) . ? S6 O8 1.4575(16) . ? S6 C36 1.827(3) . ? F1 C33 1.328(3) . ? F2 C33 1.334(3) . ? F3 C33 1.338(3) . ? F6 C36 1.332(3) . ? F7 C36 1.326(3) . ? F8 C36 1.330(3) . ? O1 N9 1.217(2) . ? O2 N9 1.233(2) . ? O5 Eu1 2.2710(17) 2_655 ? N1 C18 1.338(3) . ? N1 C15 1.350(3) . ? N2 C2 1.328(3) . ? N2 C1 1.339(3) . ? N3 C14 1.343(3) . ? N3 C6 1.348(3) . ? N7 C29 1.484(3) . ? N7 C38 1.487(3) . ? N7 C31 1.488(3) . ? N9 C2 1.479(3) . ? C1 C5 1.399(3) . ? C1 C29 1.502(3) . ? C2 C3 1.373(3) . ? C3 C4 1.389(4) . ? C3 H3 0.9500 . ? C4 C5 1.384(3) . ? C4 H4 0.9500 . ? C5 H5 0.9500 . ? C6 C7 1.387(3) . ? C6 C38 1.504(3) . ? C7 C8 1.381(4) . ? C7 H7 0.9500 . ? C8 C9 1.380(4) . ? C8 H8 0.9500 . ? C9 C14 1.388(3) . ? C9 H9 0.9500 . ? C14 H14 0.9500 . ? C15 C16 1.385(3) . ? C15 C31 1.506(3) . ? C16 C17 1.390(3) . ? C16 H16 0.9500 . ? C17 C27 1.378(4) . ? C17 H17 0.9500 . ? C18 C27 1.390(3) . ? C18 H18 0.9500 . ? C27 H27 0.9500 . ? C29 H29A 0.9900 . ? C29 H29B 0.9900 . ? C31 H31A 0.9900 . ? C31 H31B 0.9900 . ? C38 H38A 0.9900 . ? C38 H38B 0.9900 . ? N11 C41 1.115(5) . ? C41 C42 1.41(2) . ? C41 C43 1.54(2) . ? C42 H42A 0.9800 . ? C42 H42B 0.9800 . ? C42 H42C 0.9800 . ? C43 H43A 0.9800 . ? C43 H43B 0.9800 . ? C43 H43C 0.9800 . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag O5 Eu1 O5 66.84(7) 2_655 . ? O5 Eu1 O13 135.48(6) 2_655 . ? O5 Eu1 O13 74.58(6) . . ? O5 Eu1 O8 78.51(6) 2_655 . ? O5 Eu1 O8 143.47(5) . . ? O13 Eu1 O8 129.61(5) . . ? O5 Eu1 O2 76.37(6) 2_655 . ? O5 Eu1 O2 77.73(6) . . ? O13 Eu1 O2 74.47(5) . . ? O8 Eu1 O2 83.40(5) . . ? O5 Eu1 N3 81.23(7) 2_655 . ? O5 Eu1 N3 112.46(6) . . ? O13 Eu1 N3 135.71(6) . . ? O8 Eu1 N3 71.42(6) . . ? O2 Eu1 N3 149.13(5) . . ? O5 Eu1 N1 119.32(6) 2_655 . ? O5 Eu1 N1 77.98(6) . . ? O13 Eu1 N1 70.90(6) . . ? O8 Eu1 N1 131.84(6) . . ? O2 Eu1 N1 141.79(6) . . ? N3 Eu1 N1 68.43(6) . . ? O5 Eu1 N2 126.03(6) 2_655 . ? O5 Eu1 N2 125.09(6) . . ? O13 Eu1 N2 62.34(6) . . ? O8 Eu1 N2 67.36(6) . . ? O2 Eu1 N2 59.77(6) . . ? N3 Eu1 N2 121.96(6) . . ? N1 Eu1 N2 114.61(6) . . ? O5 Eu1 N7 143.50(6) 2_655 . ? O5 Eu1 N7 141.15(6) . . ? O13 Eu1 N7 81.03(6) . . ? O8 Eu1 N7 74.99(6) . . ? O2 Eu1 N7 124.09(6) . . ? N3 Eu1 N7 66.84(6) . . ? N1 Eu1 N7 65.56(6) . . ? N2 Eu1 N7 64.32(6) . . ? O5 Eu1 Eu1 33.79(4) 2_655 2_655 ? O5 Eu1 Eu1 33.04(4) . 2_655 ? O13 Eu1 Eu1 105.19(5) . 2_655 ? O8 Eu1 Eu1 111.59(4) . 2_655 ? O2 Eu1 Eu1 74.44(4) . 2_655 ? N3 Eu1 Eu1 98.09(5) . 2_655 ? N1 Eu1 Eu1 99.47(5) . 2_655 ? N2 Eu1 Eu1 134.16(4) . 2_655 ? N7 Eu1 Eu1 161.42(4) . 2_655 ? O17 S3 O14 116.59(11) . . ? O17 S3 O13 114.17(11) . . ? O14 S3 O13 114.04(10) . . ? O17 S3 C33 104.42(11) . . ? O14 S3 C33 104.71(11) . . ? O13 S3 C33 100.41(10) . . ? O7 S6 O9 116.74(11) . . ? O7 S6 O8 113.94(10) . . ? O9 S6 O8 114.15(10) . . ? O7 S6 C36 103.42(12) . . ? O9 S6 C36 103.81(12) . . ? O8 S6 C36 102.35(11) . . ? N9 O2 Eu1 125.99(13) . . ? Eu1 O5 Eu1 113.16(7) 2_655 . ? S6 O8 Eu1 138.47(10) . . ? S3 O13 Eu1 147.37(10) . . ? C18 N1 C15 118.11(19) . . ? C18 N1 Eu1 123.52(14) . . ? C15 N1 Eu1 118.20(14) . . ? C2 N2 C1 116.55(19) . . ? C2 N2 Eu1 121.26(14) . . ? C1 N2 Eu1 120.59(14) . . ? C14 N3 C6 117.7(2) . . ? C14 N3 Eu1 121.74(15) . . ? C6 N3 Eu1 119.28(15) . . ? C29 N7 C38 107.78(17) . . ? C29 N7 C31 107.57(17) . . ? C38 N7 C31 110.07(17) . . ? C29 N7 Eu1 114.48(13) . . ? C38 N7 Eu1 111.54(13) . . ? C31 N7 Eu1 105.28(13) . . ? O1 N9 O2 123.7(2) . . ? O1 N9 C2 118.37(19) . . ? O2 N9 C2 117.91(18) . . ? N2 C1 C5 121.6(2) . . ? N2 C1 C29 117.07(19) . . ? C5 C1 C29 121.0(2) . . ? N2 C2 C3 127.1(2) . . ? N2 C2 N9 113.44(19) . . ? C3 C2 N9 119.5(2) . . ? C2 C3 C4 115.7(2) . . ? C2 C3 H3 122.1 . . ? C4 C3 H3 122.1 . . ? C5 C4 C3 119.5(2) . . ? C5 C4 H4 120.2 . . ? C3 C4 H4 120.2 . . ? C4 C5 C1 119.4(2) . . ? C4 C5 H5 120.3 . . ? C1 C5 H5 120.3 . . ? N3 C6 C7 122.3(2) . . ? N3 C6 C38 117.90(19) . . ? C7 C6 C38 119.3(2) . . ? C8 C7 C6 119.4(2) . . ? C8 C7 H7 120.3 . . ? C6 C7 H7 120.3 . . ? C9 C8 C7 118.8(2) . . ? C9 C8 H8 120.6 . . ? C7 C8 H8 120.6 . . ? C8 C9 C14 118.8(2) . . ? C8 C9 H9 120.6 . . ? C14 C9 H9 120.6 . . ? N3 C14 C9 123.1(2) . . ? N3 C14 H14 118.5 . . ? C9 C14 H14 118.5 . . ? N1 C15 C16 122.3(2) . . ? N1 C15 C31 116.81(19) . . ? C16 C15 C31 120.8(2) . . ? C15 C16 C17 119.1(2) . . ? C15 C16 H16 120.5 . . ? C17 C16 H16 120.5 . . ? C27 C17 C16 118.8(2) . . ? C27 C17 H17 120.6 . . ? C16 C17 H17 120.6 . . ? N1 C18 C27 122.7(2) . . ? N1 C18 H18 118.6 . . ? C27 C18 H18 118.6 . . ? C17 C27 C18 119.0(2) . . ? C17 C27 H27 120.5 . . ? C18 C27 H27 120.5 . . ? N7 C29 C1 114.07(18) . . ? N7 C29 H29A 108.7 . . ? C1 C29 H29A 108.7 . . ? N7 C29 H29B 108.7 . . ? C1 C29 H29B 108.7 . . ? H29A C29 H29B 107.6 . . ? N7 C31 C15 112.66(18) . . ? N7 C31 H31A 109.1 . . ? C15 C31 H31A 109.1 . . ? N7 C31 H31B 109.1 . . ? C15 C31 H31B 109.1 . . ? H31A C31 H31B 107.8 . . ? F1 C33 F2 107.7(2) . . ? F1 C33 F3 107.8(2) . . ? F2 C33 F3 107.6(2) . . ? F1 C33 S3 111.33(17) . . ? F2 C33 S3 111.19(17) . . ? F3 C33 S3 111.09(17) . . ? F7 C36 F8 108.2(2) . . ? F7 C36 F6 107.4(2) . . ? F8 C36 F6 107.8(2) . . ? F7 C36 S6 110.90(18) . . ? F8 C36 S6 110.77(18) . . ? F6 C36 S6 111.63(17) . . ? N7 C38 C6 116.44(18) . . ? N7 C38 H38A 108.2 . . ? C6 C38 H38A 108.2 . . ? N7 C38 H38B 108.2 . . ? C6 C38 H38B 108.2 . . ? H38A C38 H38B 107.3 . . ? N11 C41 C42 166.1(11) . . ? N11 C41 C43 167(2) . . ? C42 C41 C43 26.7(17) . . ? C41 C42 H42A 109.5 . . ? C41 C42 H42B 109.5 . . ? C41 C42 H42C 109.5 . . ? C41 C43 H43A 109.5 . . ? C41 C43 H43B 109.5 . . ? H43A C43 H43B 109.5 . . ? C41 C43 H43C 109.5 . . ? H43A C43 H43C 109.5 . . ? H43B C43 H43C 109.5 . . ? _diffrn_measured_fraction_theta_max 0.996 _diffrn_reflns_theta_full 27.50 _diffrn_measured_fraction_theta_full 0.996 _refine_diff_density_max 1.103 _refine_diff_density_min -0.524 _refine_diff_density_rms 0.091