# Electronic Supplementary Material (ESI) for Dalton Transactions # This journal is © The Royal Society of Chemistry 2013 ####################################################################### # # 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_shelxs1 _database_code_depnum_ccdc_archive 'CCDC 896127' #TrackingRef '1.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C21 H24 Eu N4 O11' _chemical_formula_weight 660.40 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Eu Eu -0.1578 3.6682 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting triclinic _symmetry_space_group_name_H-M p-1 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 9.9544(6) _cell_length_b 11.7155(7) _cell_length_c 13.5215(8) _cell_angle_alpha 66.8970(10) _cell_angle_beta 87.033(2) _cell_angle_gamma 76.402(2) _cell_volume 1408.32(15) _cell_formula_units_Z 2 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 10617 _cell_measurement_theta_min 3.09 _cell_measurement_theta_max 27.57 _exptl_crystal_description ? _exptl_crystal_colour ? _exptl_crystal_size_max 0.10 _exptl_crystal_size_mid 0.06 _exptl_crystal_size_min 0.04 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.557 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 658 _exptl_absorpt_coefficient_mu 2.285 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.8037 _exptl_absorpt_correction_T_max 0.9141 _exptl_absorpt_process_details sadabs _exptl_special_details ; ? ; _diffrn_ambient_temperature 293(2) _diffrn_radiation_wavelength 0.71075 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type ? _diffrn_measurement_method ? _diffrn_detector_area_resol_mean ? _diffrn_standards_number . _diffrn_standards_interval_count . _diffrn_standards_interval_time . _diffrn_standards_decay_% . _diffrn_reflns_number 8977 _diffrn_reflns_av_R_equivalents 0.0275 _diffrn_reflns_av_sigmaI/netI 0.0415 _diffrn_reflns_limit_h_min -11 _diffrn_reflns_limit_h_max 11 _diffrn_reflns_limit_k_min -13 _diffrn_reflns_limit_k_max 13 _diffrn_reflns_limit_l_min -12 _diffrn_reflns_limit_l_max 16 _diffrn_reflns_theta_min 3.09 _diffrn_reflns_theta_max 25.01 _reflns_number_total 4931 _reflns_number_gt 4557 _reflns_threshold_expression >2sigma(I) _computing_data_collection ? _computing_cell_refinement ? _computing_data_reduction ? _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics ? _computing_publication_material ? _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0702P)^2^+2.7154P] 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 constra _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 4931 _refine_ls_number_parameters 336 _refine_ls_number_restraints 222 _refine_ls_R_factor_all 0.0452 _refine_ls_R_factor_gt 0.0407 _refine_ls_wR_factor_ref 0.1218 _refine_ls_wR_factor_gt 0.1190 _refine_ls_goodness_of_fit_ref 1.180 _refine_ls_restrained_S_all 1.190 _refine_ls_shift/su_max 0.004 _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 0.26380(3) -0.02657(3) 0.99528(2) 0.01562(13) Uani 1 1 d U . . C1 C -0.2110(6) 0.7090(6) 0.1588(5) 0.0253(14) Uani 1 1 d U . . C2 C -0.4001(8) 0.5979(9) 0.4153(7) 0.054(2) Uani 1 1 d U . . H2 H -0.4870 0.6209 0.4402 0.065 Uiso 1 1 calc R . . C3 C -0.3761(7) 0.6674(7) 0.3090(6) 0.0387(18) Uani 1 1 d U . . H3 H -0.4448 0.7336 0.2638 0.046 Uiso 1 1 calc R . . C4 C -0.2468(7) 0.6348(6) 0.2728(5) 0.0249(14) Uani 1 1 d U . . C5 C -0.1493(6) 0.5330(6) 0.3430(5) 0.0242(13) Uani 1 1 d U . . H5 H -0.0615 0.5083 0.3202 0.029 Uiso 1 1 calc R . . C6 C -0.1842(6) 0.4689(6) 0.4466(5) 0.0279(15) Uani 1 1 d U . . C7 C -0.0820(7) 0.3595(6) 0.5243(5) 0.0278(14) Uani 1 1 d U . . C8 C -0.1104(6) 0.2994(6) 0.6324(5) 0.0240(13) Uani 1 1 d U . . H8 H -0.1960 0.3256 0.6576 0.029 Uiso 1 1 calc R . . C9 C -0.0110(6) 0.2016(6) 0.7011(5) 0.0213(13) Uani 1 1 d U . . C10 C 0.1156(7) 0.1661(7) 0.6602(6) 0.0340(16) Uani 1 1 d U . . H10 H 0.1866 0.1023 0.7048 0.041 Uiso 1 1 calc R . . C11 C 0.1336(8) 0.2274(8) 0.5523(6) 0.045(2) Uani 1 1 d U . . H11 H 0.2172 0.2004 0.5251 0.054 Uiso 1 1 calc R . . C12 C -0.0349(6) 0.1331(6) 0.8179(5) 0.0192(12) Uani 1 1 d U . . C13 C 0.4882(6) 0.0034(6) 1.1764(5) 0.0192(12) Uani 1 1 d U . . C14 C 0.2742(9) -0.0707(11) 1.4227(7) 0.062(3) Uani 1 1 d U . . H14 H 0.1915 -0.0955 1.4433 0.074 Uiso 1 1 calc R . . C15 C 0.3150(8) -0.0545(9) 1.3203(6) 0.048(2) Uani 1 1 d U . . H15 H 0.2624 -0.0700 1.2741 0.057 Uiso 1 1 calc R . . C16 C 0.4353(6) -0.0149(6) 1.2877(5) 0.0256(14) Uani 1 1 d U . . C17 C 0.5101(7) 0.0070(7) 1.3591(5) 0.0273(14) Uani 1 1 d U . . H17 H 0.5919 0.0336 1.3391 0.033 Uiso 1 1 calc R . . C18 C 0.4617(7) -0.0112(7) 1.4606(5) 0.0333(16) Uani 1 1 d U . . C19 C 0.203(2) -0.2924(19) 0.7263(15) 0.167(8) Uani 1 1 d U . . H19A H 0.2859 -0.2662 0.6958 0.250 Uiso 1 1 calc R . . H19B H 0.1240 -0.2319 0.6839 0.250 Uiso 1 1 calc R . . H19C H 0.2060 -0.3751 0.7271 0.250 Uiso 1 1 calc R . . C20 C 0.1371(18) -0.3937(13) 0.9169(13) 0.117(5) Uani 1 1 d U . . H20A H 0.1446 -0.3909 0.9864 0.175 Uiso 1 1 calc R . . H20B H 0.1859 -0.4760 0.9194 0.175 Uiso 1 1 calc R . . H20C H 0.0413 -0.3792 0.8973 0.175 Uiso 1 1 calc R . . C21 C 0.2272(9) -0.2097(9) 0.8631(8) 0.053(2) Uani 1 1 d U . . H21 H 0.2693 -0.1524 0.8101 0.064 Uiso 1 1 calc R . . N1 N -0.3079(6) 0.5008(7) 0.4845(5) 0.0467(18) Uani 1 1 d U . . N2 N 0.0401(6) 0.3219(6) 0.4849(5) 0.0404(15) Uani 1 1 d U . . N3 N 0.3453(7) -0.0532(8) 1.4944(5) 0.0522(19) Uani 1 1 d U . . N4 N 0.1949(10) -0.2983(9) 0.8399(7) 0.070(2) Uani 1 1 d U . . O1 O -0.2950(4) 0.8136(4) 0.1069(4) 0.0265(10) Uani 1 1 d U . . O2 O -0.1018(5) 0.6640(5) 0.1234(4) 0.0418(13) Uani 1 1 d U . . O3 O -0.1566(4) 0.1503(4) 0.8485(3) 0.0259(10) Uani 1 1 d U . . O4 O 0.0680(4) 0.0587(4) 0.8784(3) 0.0279(10) Uani 1 1 d U . . O5 O 0.2080(5) -0.1944(5) 0.9467(4) 0.0350(11) Uani 1 1 d U . . O6 O 0.6043(4) 0.0273(4) 1.1585(3) 0.0248(10) Uani 1 1 d U . . O7 O 0.4127(4) -0.0076(4) 1.1118(3) 0.0260(10) Uani 1 1 d U . . O8 O 0.4520(4) -0.2179(4) 1.0605(4) 0.0299(10) Uani 1 1 d U . . H8A H 0.5376 -0.2532 1.0743 0.045 Uiso 1 1 d R . . H8B H 0.4133 -0.2696 1.0495 0.045 Uiso 1 1 d R . . O9 O 0.1057(4) 0.1267(4) 1.0594(4) 0.0278(10) Uani 1 1 d U . . H9A H 0.0188 0.1572 1.0504 0.042 Uiso 1 1 d R . . H9B H 0.1446 0.1891 1.0382 0.042 Uiso 1 1 d R . . O10 O 0.3254(12) 0.4075(11) 0.1915(9) 0.137(4) Uani 1 1 d U . . O11 O 0.4374(13) 0.3425(11) 0.0820(10) 0.147(5) Uani 1 1 d U . . H11A H 0.4588 0.3697 0.0165 0.220 Uiso 1 1 d R . . H11B H 0.4527 0.2617 0.1054 0.220 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 Eu1 0.01607(18) 0.01931(19) 0.01017(18) -0.00377(13) -0.00037(11) -0.00501(12) C1 0.026(3) 0.023(3) 0.023(3) -0.003(3) 0.000(3) -0.008(3) C2 0.031(4) 0.054(5) 0.045(5) 0.004(4) 0.009(3) 0.004(4) C3 0.027(3) 0.036(4) 0.031(4) 0.007(3) -0.003(3) 0.001(3) C4 0.028(3) 0.023(3) 0.022(3) -0.006(3) 0.001(3) -0.008(3) C5 0.022(3) 0.025(3) 0.021(3) -0.005(3) -0.002(2) -0.003(3) C6 0.023(3) 0.029(3) 0.021(3) 0.002(3) 0.000(2) -0.006(3) C7 0.028(3) 0.028(3) 0.022(3) -0.004(3) 0.002(3) -0.008(3) C8 0.021(3) 0.028(3) 0.021(3) -0.007(3) 0.005(2) -0.007(3) C9 0.022(3) 0.019(3) 0.018(3) 0.000(2) -0.001(2) -0.008(2) C10 0.029(3) 0.033(4) 0.027(3) -0.003(3) 0.003(3) 0.001(3) C11 0.036(4) 0.050(5) 0.026(4) -0.002(3) 0.008(3) 0.010(3) C12 0.022(3) 0.020(3) 0.017(3) -0.006(2) -0.003(2) -0.008(2) C13 0.019(3) 0.024(3) 0.015(3) -0.009(2) 0.002(2) -0.003(2) C14 0.054(5) 0.113(7) 0.045(5) -0.041(5) 0.020(4) -0.057(5) C15 0.044(4) 0.083(6) 0.036(4) -0.033(4) 0.011(3) -0.038(4) C16 0.024(3) 0.034(4) 0.020(3) -0.010(3) 0.000(2) -0.008(3) C17 0.025(3) 0.042(4) 0.020(3) -0.014(3) 0.005(2) -0.014(3) C18 0.031(3) 0.050(4) 0.025(3) -0.017(3) 0.003(3) -0.015(3) C19 0.228(16) 0.183(15) 0.166(14) -0.139(12) 0.002(12) -0.063(12) C20 0.165(13) 0.084(9) 0.131(12) -0.051(8) 0.018(10) -0.069(9) C21 0.064(5) 0.063(5) 0.058(5) -0.041(4) 0.017(4) -0.036(4) N1 0.030(3) 0.051(4) 0.030(3) 0.008(3) 0.004(3) 0.001(3) N2 0.035(3) 0.044(4) 0.023(3) -0.001(3) 0.007(2) 0.002(3) N3 0.049(4) 0.099(5) 0.031(3) -0.035(4) 0.016(3) -0.045(4) N4 0.093(6) 0.078(5) 0.077(5) -0.058(4) 0.024(4) -0.047(4) O1 0.022(2) 0.020(2) 0.025(2) 0.0030(19) -0.0015(18) -0.0028(18) O2 0.043(3) 0.031(3) 0.031(3) 0.002(2) 0.010(2) 0.003(2) O3 0.026(2) 0.028(2) 0.019(2) -0.0035(19) 0.0071(18) -0.0087(19) O4 0.020(2) 0.036(3) 0.020(2) -0.002(2) -0.0067(18) -0.0069(19) O5 0.034(3) 0.042(3) 0.044(3) -0.028(2) 0.006(2) -0.017(2) O6 0.027(2) 0.039(3) 0.014(2) -0.0125(19) 0.0060(17) -0.016(2) O7 0.030(2) 0.039(3) 0.014(2) -0.015(2) -0.0018(18) -0.009(2) O8 0.022(2) 0.027(2) 0.038(3) -0.011(2) -0.0058(19) -0.0015(19) O9 0.025(2) 0.027(2) 0.029(2) -0.010(2) 0.0062(19) -0.0064(19) O10 0.151(9) 0.124(8) 0.099(7) -0.032(6) 0.010(7) 0.019(7) O11 0.178(10) 0.115(8) 0.158(10) -0.082(8) -0.026(8) 0.002(7) _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 O7 2.324(4) . ? Eu1 O4 2.336(4) . ? Eu1 O6 2.403(4) 2_657 ? Eu1 O3 2.407(4) 2_557 ? Eu1 O1 2.418(4) 2_566 ? Eu1 O8 2.441(4) . ? Eu1 O5 2.484(5) . ? Eu1 O9 2.491(4) . ? Eu1 H8B 2.7091 . ? Eu1 H9B 2.7920 . ? C1 O2 1.250(8) . ? C1 O1 1.264(8) . ? C1 C4 1.515(9) . ? C2 N1 1.332(10) . ? C2 C3 1.388(11) . ? C2 H2 0.9300 . ? C3 C4 1.375(10) . ? C3 H3 0.9300 . ? C4 C5 1.388(9) . ? C5 C6 1.376(9) . ? C5 H5 0.9300 . ? C6 N1 1.337(9) . ? C6 C7 1.491(9) . ? C7 N2 1.349(9) . ? C7 C8 1.399(9) . ? C8 C9 1.371(9) . ? C8 H8 0.9300 . ? C9 C10 1.388(9) . ? C9 C12 1.500(8) . ? C10 C11 1.374(10) . ? C10 H10 0.9300 . ? C11 N2 1.316(9) . ? C11 H11 0.9300 . ? C12 O3 1.256(7) . ? C12 O4 1.260(7) . ? C13 O6 1.241(7) . ? C13 O7 1.244(7) . ? C13 C16 1.519(8) . ? C14 N3 1.333(10) . ? C14 C15 1.375(11) . ? C14 H14 0.9300 . ? C15 C16 1.374(10) . ? C15 H15 0.9300 . ? C16 C17 1.383(9) . ? C17 C18 1.382(9) . ? C17 H17 0.9300 . ? C18 N3 1.353(9) . ? C18 C18 1.479(13) 2_658 ? C19 N4 1.508(18) . ? C19 H19A 0.9600 . ? C19 H19B 0.9600 . ? C19 H19C 0.9600 . ? C20 N4 1.411(15) . ? C20 H20A 0.9600 . ? C20 H20B 0.9600 . ? C20 H20C 0.9600 . ? C21 O5 1.211(9) . ? C21 N4 1.306(11) . ? C21 H21 0.9300 . ? O1 Eu1 2.418(4) 2_566 ? O3 Eu1 2.407(4) 2_557 ? O6 Eu1 2.403(4) 2_657 ? O8 H8A 0.8500 . ? O8 H8B 0.8499 . ? O9 H9A 0.8500 . ? O9 H9B 0.8500 . ? O11 H11A 0.8500 . ? O11 H11B 0.8501 . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag O7 Eu1 O4 150.18(16) . . ? O7 Eu1 O6 105.62(15) . 2_657 ? O4 Eu1 O6 86.72(15) . 2_657 ? O7 Eu1 O3 87.71(15) . 2_557 ? O4 Eu1 O3 97.05(15) . 2_557 ? O6 Eu1 O3 145.95(16) 2_657 2_557 ? O7 Eu1 O1 79.06(16) . 2_566 ? O4 Eu1 O1 79.55(15) . 2_566 ? O6 Eu1 O1 71.20(15) 2_657 2_566 ? O3 Eu1 O1 142.81(15) 2_557 2_566 ? O7 Eu1 O8 70.46(15) . . ? O4 Eu1 O8 139.32(16) . . ? O6 Eu1 O8 73.84(16) 2_657 . ? O3 Eu1 O8 81.82(15) 2_557 . ? O1 Eu1 O8 124.42(15) 2_566 . ? O7 Eu1 O5 139.33(17) . . ? O4 Eu1 O5 69.84(17) . . ? O6 Eu1 O5 73.78(15) 2_657 . ? O3 Eu1 O5 75.87(16) 2_557 . ? O1 Eu1 O5 134.22(16) 2_566 . ? O8 Eu1 O5 70.52(16) . . ? O7 Eu1 O9 79.05(15) . . ? O4 Eu1 O9 74.38(16) . . ? O6 Eu1 O9 139.72(15) 2_657 . ? O3 Eu1 O9 72.85(15) 2_557 . ? O1 Eu1 O9 70.58(15) 2_566 . ? O8 Eu1 O9 140.88(15) . . ? O5 Eu1 O9 128.31(15) . . ? O7 Eu1 H8B 87.3 . . ? O4 Eu1 H8B 122.4 . . ? O6 Eu1 H8B 74.1 2_657 . ? O3 Eu1 H8B 75.4 2_557 . ? O1 Eu1 H8B 137.4 2_566 . ? O8 Eu1 H8B 18.0 . . ? O5 Eu1 H8B 52.8 . . ? O9 Eu1 H8B 145.8 . . ? O7 Eu1 H9B 71.2 . . ? O4 Eu1 H9B 79.5 . . ? O6 Eu1 H9B 125.5 2_657 . ? O3 Eu1 H9B 88.3 2_557 . ? O1 Eu1 H9B 54.6 2_566 . ? O8 Eu1 H9B 140.6 . . ? O5 Eu1 H9B 143.1 . . ? O9 Eu1 H9B 17.3 . . ? H8B Eu1 H9B 153.6 . . ? O2 C1 O1 125.0(6) . . ? O2 C1 C4 118.5(6) . . ? O1 C1 C4 116.5(6) . . ? N1 C2 C3 124.8(7) . . ? N1 C2 H2 117.6 . . ? C3 C2 H2 117.6 . . ? C4 C3 C2 117.5(7) . . ? C4 C3 H3 121.2 . . ? C2 C3 H3 121.2 . . ? C3 C4 C5 118.8(6) . . ? C3 C4 C1 120.7(6) . . ? C5 C4 C1 120.6(6) . . ? C6 C5 C4 119.1(6) . . ? C6 C5 H5 120.4 . . ? C4 C5 H5 120.4 . . ? N1 C6 C5 123.2(6) . . ? N1 C6 C7 116.1(6) . . ? C5 C6 C7 120.6(6) . . ? N2 C7 C8 121.6(6) . . ? N2 C7 C6 116.4(6) . . ? C8 C7 C6 122.0(6) . . ? C9 C8 C7 119.5(6) . . ? C9 C8 H8 120.3 . . ? C7 C8 H8 120.3 . . ? C8 C9 C10 118.3(6) . . ? C8 C9 C12 122.1(5) . . ? C10 C9 C12 119.6(6) . . ? C11 C10 C9 118.5(6) . . ? C11 C10 H10 120.7 . . ? C9 C10 H10 120.7 . . ? N2 C11 C10 124.3(7) . . ? N2 C11 H11 117.9 . . ? C10 C11 H11 117.9 . . ? O3 C12 O4 124.1(6) . . ? O3 C12 C9 118.2(5) . . ? O4 C12 C9 117.7(5) . . ? O6 C13 O7 125.8(5) . . ? O6 C13 C16 116.6(5) . . ? O7 C13 C16 117.6(5) . . ? N3 C14 C15 124.4(7) . . ? N3 C14 H14 117.8 . . ? C15 C14 H14 117.8 . . ? C16 C15 C14 118.5(7) . . ? C16 C15 H15 120.7 . . ? C14 C15 H15 120.7 . . ? C15 C16 C17 118.7(6) . . ? C15 C16 C13 121.7(6) . . ? C17 C16 C13 119.6(6) . . ? C18 C17 C16 119.2(6) . . ? C18 C17 H17 120.4 . . ? C16 C17 H17 120.4 . . ? N3 C18 C17 122.6(6) . . ? N3 C18 C18 116.4(8) . 2_658 ? C17 C18 C18 121.0(8) . 2_658 ? N4 C19 H19A 109.5 . . ? N4 C19 H19B 109.5 . . ? H19A C19 H19B 109.5 . . ? N4 C19 H19C 109.5 . . ? H19A C19 H19C 109.5 . . ? H19B C19 H19C 109.5 . . ? N4 C20 H20A 109.5 . . ? N4 C20 H20B 109.5 . . ? H20A C20 H20B 109.5 . . ? N4 C20 H20C 109.5 . . ? H20A C20 H20C 109.5 . . ? H20B C20 H20C 109.5 . . ? O5 C21 N4 126.7(9) . . ? O5 C21 H21 116.7 . . ? N4 C21 H21 116.7 . . ? C2 N1 C6 116.4(6) . . ? C11 N2 C7 117.8(6) . . ? C14 N3 C18 116.5(6) . . ? C21 N4 C20 121.0(10) . . ? C21 N4 C19 120.5(11) . . ? C20 N4 C19 118.2(11) . . ? C1 O1 Eu1 132.4(4) . 2_566 ? C12 O3 Eu1 131.8(4) . 2_557 ? C12 O4 Eu1 163.8(4) . . ? C21 O5 Eu1 128.3(5) . . ? C13 O6 Eu1 125.5(4) . 2_657 ? C13 O7 Eu1 177.6(4) . . ? Eu1 O8 H8A 150.5 . . ? Eu1 O8 H8B 99.2 . . ? H8A O8 H8B 107.7 . . ? Eu1 O9 H9A 131.7 . . ? Eu1 O9 H9B 101.8 . . ? H9A O9 H9B 107.7 . . ? H11A O11 H11B 107.7 . . ? _diffrn_measured_fraction_theta_max 0.997 _diffrn_reflns_theta_full 25.01 _diffrn_measured_fraction_theta_full 0.997 _refine_diff_density_max 1.734 _refine_diff_density_min -1.188 _refine_diff_density_rms 0.180 data_shelxs2 _database_code_depnum_ccdc_archive 'CCDC 896128' #TrackingRef '2.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C21 H24 Gd N4 O11' _chemical_formula_weight 665.69 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0000 0.0000 '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' Gd Gd 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting triclinic _symmetry_space_group_name_H-M p-1 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 9.9008(13) _cell_length_b 11.6556(16) _cell_length_c 13.4354(18) _cell_angle_alpha 66.832(3) _cell_angle_beta 87.019(3) _cell_angle_gamma 76.377(3) _cell_volume 1383.9(3) _cell_formula_units_Z 2 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 9774 _cell_measurement_theta_min 3.105 _cell_measurement_theta_max 27.82 _exptl_crystal_description ? _exptl_crystal_colour ? _exptl_crystal_size_max 0.80 _exptl_crystal_size_mid 0.30 _exptl_crystal_size_min 0.20 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.598 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 660 _exptl_absorpt_coefficient_mu 2.456 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.2440 _exptl_absorpt_correction_T_max 0.6394 _exptl_absorpt_process_details sadabs _exptl_special_details ; ? ; _diffrn_ambient_temperature 293(2) _diffrn_radiation_wavelength 0.71075 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type ? _diffrn_measurement_method ? _diffrn_detector_area_resol_mean ? _diffrn_standards_number . _diffrn_standards_interval_count . _diffrn_standards_interval_time . _diffrn_standards_decay_% . _diffrn_reflns_number 10529 _diffrn_reflns_av_R_equivalents 0.0880 _diffrn_reflns_av_sigmaI/netI 0.1460 _diffrn_reflns_limit_h_min -12 _diffrn_reflns_limit_h_max 11 _diffrn_reflns_limit_k_min -15 _diffrn_reflns_limit_k_max 14 _diffrn_reflns_limit_l_min -17 _diffrn_reflns_limit_l_max 17 _diffrn_reflns_theta_min 3.11 _diffrn_reflns_theta_max 27.48 _reflns_number_total 6169 _reflns_number_gt 4628 _reflns_threshold_expression >2sigma(I) _computing_data_collection ? _computing_cell_refinement ? _computing_data_reduction ? _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics ? _computing_publication_material ? _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.1043P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment constra _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 6169 _refine_ls_number_parameters 336 _refine_ls_number_restraints 222 _refine_ls_R_factor_all 0.1237 _refine_ls_R_factor_gt 0.0890 _refine_ls_wR_factor_ref 0.2201 _refine_ls_wR_factor_gt 0.1974 _refine_ls_goodness_of_fit_ref 1.100 _refine_ls_restrained_S_all 1.098 _refine_ls_shift/su_max 0.001 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group Gd1 Gd 0.23628(5) 0.02631(5) 1.00484(4) 0.0216(2) Uani 1 1 d U . . C1 C 0.2899(12) 0.7104(11) 0.1585(9) 0.033(3) Uani 1 1 d U . . C2 C 0.0998(15) 0.6011(14) 0.4171(11) 0.058(4) Uani 1 1 d U . . H2A H 0.0145 0.6274 0.4434 0.069 Uiso 1 1 calc R . . C3 C 0.1244(13) 0.6673(13) 0.3115(9) 0.042(3) Uani 1 1 d U . . H3A H 0.0548 0.7334 0.2660 0.050 Uiso 1 1 calc R . . C4 C 0.2507(12) 0.6357(11) 0.2737(8) 0.031(3) Uani 1 1 d U . . C5 C 0.3503(11) 0.5325(10) 0.3437(8) 0.029(2) Uani 1 1 d U . . H5A H 0.4376 0.5066 0.3198 0.035 Uiso 1 1 calc R . . C6 C 0.3174(12) 0.4713(11) 0.4464(9) 0.032(3) Uani 1 1 d U . . C7 C 0.4198(12) 0.3593(11) 0.5248(8) 0.032(3) Uani 1 1 d U . . C8 C 0.3908(12) 0.2994(11) 0.6322(8) 0.029(2) Uani 1 1 d U . . H8A H 0.3044 0.3259 0.6568 0.035 Uiso 1 1 calc R . . C9 C 0.4893(11) 0.2014(11) 0.7019(8) 0.025(2) Uani 1 1 d U . . C10 C 0.6140(13) 0.1651(12) 0.6608(9) 0.037(3) Uani 1 1 d U . . H10A H 0.6844 0.0995 0.7057 0.044 Uiso 1 1 calc R . . C11 C 0.6338(14) 0.2264(13) 0.5527(9) 0.045(3) Uani 1 1 d U . . H11A H 0.7187 0.1998 0.5259 0.054 Uiso 1 1 calc R . . C12 C 0.4649(11) 0.1327(10) 0.8208(8) 0.024(2) Uani 1 1 d U . . C13 C 0.2278(16) 0.0703(16) 0.5767(11) 0.061(4) Uani 1 1 d U . . H13A H 0.3118 0.0936 0.5563 0.073 Uiso 1 1 calc R . . C14 C 0.1859(14) 0.0562(14) 0.6786(10) 0.047(3) Uani 1 1 d U . . H14A H 0.2374 0.0745 0.7240 0.057 Uiso 1 1 calc R . . C15 C 0.0646(12) 0.0139(11) 0.7132(8) 0.030(3) Uani 1 1 d U . . C16 C -0.0094(12) -0.0053(11) 0.6416(8) 0.030(3) Uani 1 1 d U . . H16A H -0.0928 -0.0301 0.6611 0.036 Uiso 1 1 calc R . . C17 C 0.0397(13) 0.0122(13) 0.5379(9) 0.041(3) Uani 1 1 d U . . C18 C 0.0116(11) -0.0033(10) 0.8226(8) 0.024(2) Uani 1 1 d U . . C19 C 0.362(3) 0.395(2) 1.0824(18) 0.114(8) Uani 1 1 d U . . H19C H 0.4549 0.3888 1.1044 0.172 Uiso 1 1 calc R . . H19B H 0.3039 0.4766 1.0763 0.172 Uiso 1 1 calc R . . H19A H 0.3622 0.3883 1.0135 0.172 Uiso 1 1 calc R . . C20 C 0.304(3) 0.286(3) 1.274(2) 0.174(12) Uani 1 1 d U . . H20B H 0.2642 0.3701 1.2741 0.261 Uiso 1 1 calc R . . H20C H 0.3962 0.2557 1.3068 0.261 Uiso 1 1 calc R . . H20A H 0.2474 0.2285 1.3156 0.261 Uiso 1 1 calc R . . C21 C 0.2733(17) 0.2113(16) 1.1359(12) 0.060(4) Uani 1 1 d U . . H21A H 0.2268 0.1563 1.1880 0.072 Uiso 1 1 calc R . . N1 N 0.5385(11) 0.3216(10) 0.4840(7) 0.043(3) Uani 1 1 d U . . N2 N 0.1920(12) 0.5009(11) 0.4842(8) 0.054(3) Uani 1 1 d U . . N3 N 0.1566(13) 0.0530(12) 0.5049(8) 0.052(3) Uani 1 1 d U . . N4 N 0.3083(16) 0.2938(14) 1.1614(12) 0.072(4) Uani 1 1 d U . . O1 O 0.3962(10) 0.6650(8) 0.1219(6) 0.047(2) Uani 1 1 d U . . O2 O 0.2050(8) 0.8139(7) 0.1074(5) 0.0285(17) Uani 1 1 d U . . O3 O 0.5672(8) 0.0590(8) 0.8787(6) 0.0334(19) Uani 1 1 d U . . O4 O 0.3425(7) 0.1497(7) 0.8498(5) 0.0283(17) Uani 1 1 d U . . O5 O 0.0478(8) 0.2166(8) 0.9392(6) 0.0353(19) Uani 1 1 d U . . H5C H -0.0217 0.2509 0.9661 0.053 Uiso 1 1 d R . . H5B H 0.0173 0.2044 0.8871 0.053 Uiso 1 1 d R . . O6 O 0.3956(8) -0.1256(7) 0.9393(5) 0.0311(18) Uani 1 1 d U . . H6B H 0.4622 -0.1566 0.9877 0.047 Uiso 1 1 d R . . H6A H 0.3498 -0.1852 0.9560 0.047 Uiso 1 1 d R . . O7 O -0.1056(8) -0.0277(8) 0.8420(5) 0.0308(18) Uani 1 1 d U . . O8 O 0.0898(8) 0.0064(8) 0.8889(6) 0.0322(18) Uani 1 1 d U . . O9 O 0.2920(9) 0.1946(8) 1.0541(6) 0.042(2) Uani 1 1 d U . . O10 O 0.172(2) 0.5919(19) 0.8064(14) 0.161(7) Uani 1 1 d U . . O11 O 0.936(2) 0.3394(16) 0.0850(15) 0.147(7) Uani 1 1 d U . . H11C H 0.9883 0.3893 0.0796 0.221 Uiso 1 1 d R . . H11B H 0.9351 0.2910 0.1516 0.221 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 Gd1 0.0170(3) 0.0284(3) 0.0154(3) -0.0059(2) 0.00026(18) -0.0029(2) C1 0.028(6) 0.032(6) 0.033(5) -0.005(4) -0.001(4) -0.012(5) C2 0.042(7) 0.055(7) 0.047(6) 0.003(5) 0.011(5) 0.000(6) C3 0.026(6) 0.047(7) 0.035(5) 0.000(5) 0.005(5) -0.008(5) C4 0.034(6) 0.027(5) 0.028(5) -0.005(4) -0.003(4) -0.008(5) C5 0.019(5) 0.029(5) 0.031(5) -0.006(4) 0.001(4) 0.002(4) C6 0.023(5) 0.029(6) 0.030(5) 0.002(4) -0.003(4) -0.002(4) C7 0.029(6) 0.032(6) 0.026(5) -0.003(4) 0.001(4) -0.006(5) C8 0.026(5) 0.031(6) 0.030(5) -0.009(4) 0.004(4) -0.009(4) C9 0.023(5) 0.033(5) 0.019(4) -0.009(4) -0.001(4) -0.009(4) C10 0.034(6) 0.036(6) 0.026(5) -0.003(4) 0.001(4) 0.004(5) C11 0.039(6) 0.049(7) 0.033(5) -0.011(5) 0.013(5) 0.005(5) C12 0.025(5) 0.020(5) 0.020(4) -0.001(4) -0.005(4) -0.004(4) C13 0.054(7) 0.092(9) 0.052(7) -0.036(6) 0.016(6) -0.035(7) C14 0.047(7) 0.068(8) 0.037(6) -0.024(5) -0.002(5) -0.023(6) C15 0.028(5) 0.035(6) 0.026(5) -0.010(4) 0.003(4) -0.011(5) C16 0.022(5) 0.046(6) 0.023(5) -0.016(4) 0.005(4) -0.006(5) C17 0.040(6) 0.060(7) 0.027(5) -0.019(5) 0.005(5) -0.016(5) C18 0.020(5) 0.028(5) 0.023(4) -0.013(4) 0.006(4) -0.003(4) C19 0.136(16) 0.110(14) 0.116(14) -0.051(12) 0.008(12) -0.053(13) C20 0.21(2) 0.20(2) 0.171(18) -0.126(16) -0.001(15) -0.046(15) C21 0.068(8) 0.072(8) 0.063(7) -0.041(6) 0.002(6) -0.032(6) N1 0.035(5) 0.046(6) 0.026(4) -0.002(4) 0.011(4) 0.007(4) N2 0.038(6) 0.056(6) 0.036(5) 0.008(5) 0.002(4) 0.001(5) N3 0.053(6) 0.084(7) 0.036(5) -0.033(5) 0.008(4) -0.032(5) N4 0.088(8) 0.073(7) 0.076(7) -0.046(6) 0.022(6) -0.033(6) O1 0.046(6) 0.039(5) 0.037(4) -0.004(4) 0.014(4) 0.003(4) O2 0.024(4) 0.030(4) 0.025(3) -0.003(3) -0.001(3) -0.007(3) O3 0.021(4) 0.045(5) 0.027(4) -0.006(3) -0.005(3) -0.006(3) O4 0.015(4) 0.035(4) 0.026(3) -0.006(3) 0.006(3) -0.003(3) O5 0.026(4) 0.039(5) 0.037(4) -0.016(4) -0.006(3) 0.003(4) O6 0.032(5) 0.037(5) 0.026(4) -0.013(3) 0.002(3) -0.011(4) O7 0.028(4) 0.050(5) 0.020(3) -0.017(3) 0.004(3) -0.016(4) O8 0.025(4) 0.050(5) 0.026(4) -0.022(3) -0.003(3) -0.004(3) O9 0.037(5) 0.047(5) 0.042(4) -0.018(4) -0.001(4) -0.009(4) O10 0.147(13) 0.162(14) 0.122(11) -0.037(10) -0.030(10) 0.033(11) O11 0.165(14) 0.123(12) 0.158(13) -0.069(10) -0.028(11) -0.008(10) _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 Gd1 O8 2.294(7) . ? Gd1 O3 2.325(7) 2_657 ? Gd1 O4 2.376(7) . ? Gd1 O7 2.376(7) 2_557 ? Gd1 O2 2.399(7) 1_546 ? Gd1 O5 2.421(8) . ? Gd1 O9 2.482(9) . ? Gd1 O6 2.483(8) . ? C1 O1 1.232(14) . ? C1 O2 1.251(14) . ? C1 C4 1.530(15) . ? C2 N2 1.328(16) . ? C2 C3 1.363(16) . ? C2 H2A 0.9300 . ? C3 C4 1.350(16) . ? C3 H3A 0.9300 . ? C4 C5 1.397(15) . ? C5 C6 1.344(14) . ? C5 H5A 0.9300 . ? C6 N2 1.338(16) . ? C6 C7 1.498(15) . ? C7 N1 1.324(15) . ? C7 C8 1.382(14) . ? C8 C9 1.364(15) . ? C8 H8A 0.9300 . ? C9 C10 1.369(16) . ? C9 C12 1.516(13) . ? C10 C11 1.371(15) . ? C10 H10A 0.9300 . ? C11 N1 1.329(15) . ? C11 H11A 0.9300 . ? C12 O3 1.231(12) . ? C12 O4 1.248(13) . ? C13 N3 1.326(16) . ? C13 C14 1.368(18) . ? C13 H13A 0.9300 . ? C14 C15 1.393(16) . ? C14 H14A 0.9300 . ? C15 C16 1.353(14) . ? C15 C18 1.488(14) . ? C16 C17 1.403(14) . ? C16 H16A 0.9300 . ? C17 N3 1.342(16) . ? C17 C17 1.47(2) 2_556 ? C18 O7 1.250(12) . ? C18 O8 1.264(12) . ? C19 N4 1.43(2) . ? C19 H19C 0.9600 . ? C19 H19B 0.9600 . ? C19 H19A 0.9600 . ? C20 N4 1.49(2) . ? C20 H20B 0.9600 . ? C20 H20C 0.9600 . ? C20 H20A 0.9600 . ? C21 O9 1.188(16) . ? C21 N4 1.262(18) . ? C21 H21A 0.9300 . ? O2 Gd1 2.399(7) 1_564 ? O3 Gd1 2.325(7) 2_657 ? O5 H5C 0.8500 . ? O5 H5B 0.8501 . ? O6 H6B 0.8578 . ? O6 H6A 0.8675 . ? O7 Gd1 2.376(7) 2_557 ? O11 H11C 0.8499 . ? O11 H11B 0.8499 . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag O8 Gd1 O3 149.7(3) . 2_657 ? O8 Gd1 O4 87.7(3) . . ? O3 Gd1 O4 96.8(3) 2_657 . ? O8 Gd1 O7 106.2(3) . 2_557 ? O3 Gd1 O7 86.8(3) 2_657 2_557 ? O4 Gd1 O7 145.5(3) . 2_557 ? O8 Gd1 O2 79.0(3) . 1_546 ? O3 Gd1 O2 79.6(3) 2_657 1_546 ? O4 Gd1 O2 143.1(3) . 1_546 ? O7 Gd1 O2 71.3(3) 2_557 1_546 ? O8 Gd1 O5 70.6(3) . . ? O3 Gd1 O5 139.7(3) 2_657 . ? O4 Gd1 O5 81.8(3) . . ? O7 Gd1 O5 73.8(3) 2_557 . ? O2 Gd1 O5 124.1(3) 1_546 . ? O8 Gd1 O9 139.7(3) . . ? O3 Gd1 O9 69.8(3) 2_657 . ? O4 Gd1 O9 75.9(3) . . ? O7 Gd1 O9 73.3(3) 2_557 . ? O2 Gd1 O9 134.0(3) 1_546 . ? O5 Gd1 O9 70.9(3) . . ? O8 Gd1 O6 78.7(3) . . ? O3 Gd1 O6 74.3(3) 2_657 . ? O4 Gd1 O6 72.5(3) . . ? O7 Gd1 O6 140.4(3) 2_557 . ? O2 Gd1 O6 71.2(3) 1_546 . ? O5 Gd1 O6 140.4(2) . . ? O9 Gd1 O6 128.1(3) . . ? O1 C1 O2 125.2(11) . . ? O1 C1 C4 119.8(10) . . ? O2 C1 C4 115.0(11) . . ? N2 C2 C3 123.1(14) . . ? N2 C2 H2A 118.4 . . ? C3 C2 H2A 118.4 . . ? C4 C3 C2 119.3(12) . . ? C4 C3 H3A 120.4 . . ? C2 C3 H3A 120.4 . . ? C3 C4 C5 118.4(10) . . ? C3 C4 C1 122.6(10) . . ? C5 C4 C1 118.9(10) . . ? C6 C5 C4 118.6(11) . . ? C6 C5 H5A 120.7 . . ? C4 C5 H5A 120.7 . . ? N2 C6 C5 123.3(10) . . ? N2 C6 C7 115.7(9) . . ? C5 C6 C7 120.9(11) . . ? N1 C7 C8 122.6(10) . . ? N1 C7 C6 115.6(9) . . ? C8 C7 C6 121.8(11) . . ? C9 C8 C7 119.9(11) . . ? C9 C8 H8A 120.0 . . ? C7 C8 H8A 120.0 . . ? C8 C9 C10 117.6(10) . . ? C8 C9 C12 122.6(10) . . ? C10 C9 C12 119.9(9) . . ? C9 C10 C11 119.3(11) . . ? C9 C10 H10A 120.4 . . ? C11 C10 H10A 120.4 . . ? N1 C11 C10 123.6(12) . . ? N1 C11 H11A 118.2 . . ? C10 C11 H11A 118.2 . . ? O3 C12 O4 126.0(9) . . ? O3 C12 C9 116.5(10) . . ? O4 C12 C9 117.4(9) . . ? N3 C13 C14 124.3(14) . . ? N3 C13 H13A 117.8 . . ? C14 C13 H13A 117.8 . . ? C13 C14 C15 118.9(12) . . ? C13 C14 H14A 120.6 . . ? C15 C14 H14A 120.6 . . ? C16 C15 C14 117.8(10) . . ? C16 C15 C18 120.0(10) . . ? C14 C15 C18 122.2(10) . . ? C15 C16 C17 120.1(11) . . ? C15 C16 H16A 120.0 . . ? C17 C16 H16A 120.0 . . ? N3 C17 C16 121.9(11) . . ? N3 C17 C17 118.6(13) . 2_556 ? C16 C17 C17 119.5(14) . 2_556 ? O7 C18 O8 125.3(9) . . ? O7 C18 C15 117.5(9) . . ? O8 C18 C15 117.2(9) . . ? N4 C19 H19C 109.5 . . ? N4 C19 H19B 109.5 . . ? H19C C19 H19B 109.5 . . ? N4 C19 H19A 109.5 . . ? H19C C19 H19A 109.5 . . ? H19B C19 H19A 109.5 . . ? N4 C20 H20B 109.5 . . ? N4 C20 H20C 109.5 . . ? H20B C20 H20C 109.5 . . ? N4 C20 H20A 109.5 . . ? H20B C20 H20A 109.5 . . ? H20C C20 H20A 109.5 . . ? O9 C21 N4 128.5(16) . . ? O9 C21 H21A 115.8 . . ? N4 C21 H21A 115.8 . . ? C7 N1 C11 116.9(10) . . ? C2 N2 C6 117.1(11) . . ? C13 N3 C17 116.9(11) . . ? C21 N4 C19 120.6(16) . . ? C21 N4 C20 122.0(18) . . ? C19 N4 C20 117.3(17) . . ? C1 O2 Gd1 131.7(7) . 1_564 ? C12 O3 Gd1 163.2(8) . 2_657 ? C12 O4 Gd1 131.1(6) . . ? Gd1 O5 H5C 136.4 . . ? Gd1 O5 H5B 98.1 . . ? H5C O5 H5B 107.7 . . ? Gd1 O6 H6B 100.6 . . ? Gd1 O6 H6A 99.9 . . ? H6B O6 H6A 104.7 . . ? C18 O7 Gd1 126.0(6) . 2_557 ? C18 O8 Gd1 178.2(7) . . ? C21 O9 Gd1 129.4(10) . . ? H11C O11 H11B 107.7 . . ? 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 N2 C2 C3 C4 -4(2) . . . . ? C2 C3 C4 C5 2(2) . . . . ? C2 C3 C4 C1 -176.0(13) . . . . ? O1 C1 C4 C3 -167.2(12) . . . . ? O2 C1 C4 C3 10.5(17) . . . . ? O1 C1 C4 C5 14.3(17) . . . . ? O2 C1 C4 C5 -168.0(10) . . . . ? C3 C4 C5 C6 -1.8(18) . . . . ? C1 C4 C5 C6 176.8(11) . . . . ? C4 C5 C6 N2 3(2) . . . . ? C4 C5 C6 C7 179.5(11) . . . . ? N2 C6 C7 N1 173.1(12) . . . . ? C5 C6 C7 N1 -4.0(18) . . . . ? N2 C6 C7 C8 -6.4(18) . . . . ? C5 C6 C7 C8 176.5(11) . . . . ? N1 C7 C8 C9 3.4(19) . . . . ? C6 C7 C8 C9 -177.1(11) . . . . ? C7 C8 C9 C10 -1.0(17) . . . . ? C7 C8 C9 C12 179.3(10) . . . . ? C8 C9 C10 C11 -0.9(19) . . . . ? C12 C9 C10 C11 178.8(11) . . . . ? C9 C10 C11 N1 1(2) . . . . ? C8 C9 C12 O3 -169.9(11) . . . . ? C10 C9 C12 O3 10.4(16) . . . . ? C8 C9 C12 O4 14.4(16) . . . . ? C10 C9 C12 O4 -165.3(11) . . . . ? N3 C13 C14 C15 4(3) . . . . ? C13 C14 C15 C16 -3(2) . . . . ? C13 C14 C15 C18 -179.7(13) . . . . ? C14 C15 C16 C17 2.7(19) . . . . ? C18 C15 C16 C17 179.3(11) . . . . ? C15 C16 C17 N3 -3(2) . . . . ? C15 C16 C17 C17 178.4(15) . . . 2_556 ? C16 C15 C18 O7 -4.3(17) . . . . ? C14 C15 C18 O7 172.2(12) . . . . ? C16 C15 C18 O8 174.8(11) . . . . ? C14 C15 C18 O8 -8.7(17) . . . . ? C8 C7 N1 C11 -4(2) . . . . ? C6 C7 N1 C11 177.0(12) . . . . ? C10 C11 N1 C7 1(2) . . . . ? C3 C2 N2 C6 5(2) . . . . ? C5 C6 N2 C2 -4(2) . . . . ? C7 C6 N2 C2 178.9(13) . . . . ? C14 C13 N3 C17 -4(2) . . . . ? C16 C17 N3 C13 3(2) . . . . ? C17 C17 N3 C13 -178.0(17) 2_556 . . . ? O9 C21 N4 C19 9(3) . . . . ? O9 C21 N4 C20 -167(2) . . . . ? O1 C1 O2 Gd1 -51.3(17) . . . 1_564 ? C4 C1 O2 Gd1 131.1(8) . . . 1_564 ? O4 C12 O3 Gd1 -92(3) . . . 2_657 ? C9 C12 O3 Gd1 92(3) . . . 2_657 ? O3 C12 O4 Gd1 -16.0(17) . . . . ? C9 C12 O4 Gd1 159.3(7) . . . . ? O8 Gd1 O4 C12 -120.4(9) . . . . ? O3 Gd1 O4 C12 29.6(10) 2_657 . . . ? O7 Gd1 O4 C12 123.9(9) 2_557 . . . ? O2 Gd1 O4 C12 -52.3(11) 1_546 . . . ? O5 Gd1 O4 C12 168.9(10) . . . . ? O9 Gd1 O4 C12 96.7(9) . . . . ? O6 Gd1 O4 C12 -41.6(9) . . . . ? O8 C18 O7 Gd1 11.8(16) . . . 2_557 ? C15 C18 O7 Gd1 -169.1(7) . . . 2_557 ? O7 C18 O8 Gd1 -172(23) . . . . ? C15 C18 O8 Gd1 9(25) . . . . ? O3 Gd1 O8 C18 -85(24) 2_657 . . . ? O4 Gd1 O8 C18 14(24) . . . . ? O7 Gd1 O8 C18 162(24) 2_557 . . . ? O2 Gd1 O8 C18 -131(24) 1_546 . . . ? O5 Gd1 O8 C18 96(24) . . . . ? O9 Gd1 O8 C18 79(24) . . . . ? O6 Gd1 O8 C18 -58(24) . . . . ? N4 C21 O9 Gd1 176.3(14) . . . . ? O8 Gd1 O9 C21 112.2(13) . . . . ? O3 Gd1 O9 C21 -76.1(13) 2_657 . . . ? O4 Gd1 O9 C21 -179.0(13) . . . . ? O7 Gd1 O9 C21 16.7(13) 2_557 . . . ? O2 Gd1 O9 C21 -24.4(14) 1_546 . . . ? O5 Gd1 O9 C21 94.9(13) . . . . ? O6 Gd1 O9 C21 -125.2(13) . . . . ? _diffrn_measured_fraction_theta_max 0.972 _diffrn_reflns_theta_full 27.48 _diffrn_measured_fraction_theta_full 0.972 _refine_diff_density_max 2.076 _refine_diff_density_min -2.158 _refine_diff_density_rms 0.278 data_shelxs3 _database_code_depnum_ccdc_archive 'CCDC 896129' #TrackingRef '3.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C21 H24 N4 O11 Tb' _chemical_formula_weight 667.37 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0000 0.0000 '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 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Tb Tb 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting triclinic _symmetry_space_group_name_H-M p-1 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 9.964(19) _cell_length_b 11.57(3) _cell_length_c 13.32(2) _cell_angle_alpha 67.70(8) _cell_angle_beta 87.18(4) _cell_angle_gamma 76.68(7) _cell_volume 1381(5) _cell_formula_units_Z 2 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 10591 _cell_measurement_theta_min 3.00 _cell_measurement_theta_max 27.48 _exptl_crystal_description ? _exptl_crystal_colour ? _exptl_crystal_size_max 0.10 _exptl_crystal_size_mid 0.06 _exptl_crystal_size_min 0.04 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.605 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 662 _exptl_absorpt_coefficient_mu 2.620 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.7796 _exptl_absorpt_correction_T_max 0.9025 _exptl_absorpt_process_details sadabs _exptl_special_details ; ? ; _diffrn_ambient_temperature 293(2) _diffrn_radiation_wavelength 0.71075 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type ? _diffrn_measurement_method ? _diffrn_detector_area_resol_mean ? _diffrn_standards_number . _diffrn_standards_interval_count . _diffrn_standards_interval_time . _diffrn_standards_decay_% . _diffrn_reflns_number 10591 _diffrn_reflns_av_R_equivalents 0.0615 _diffrn_reflns_av_sigmaI/netI 0.0964 _diffrn_reflns_limit_h_min -12 _diffrn_reflns_limit_h_max 12 _diffrn_reflns_limit_k_min -13 _diffrn_reflns_limit_k_max 14 _diffrn_reflns_limit_l_min -17 _diffrn_reflns_limit_l_max 17 _diffrn_reflns_theta_min 3.00 _diffrn_reflns_theta_max 27.48 _reflns_number_total 6193 _reflns_number_gt 5445 _reflns_threshold_expression >2sigma(I) _computing_data_collection ? _computing_cell_refinement ? _computing_data_reduction ? _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics ? _computing_publication_material ? _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0666P)^2^+0.3992P] 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 constra _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 6193 _refine_ls_number_parameters 336 _refine_ls_number_restraints 222 _refine_ls_R_factor_all 0.0682 _refine_ls_R_factor_gt 0.0577 _refine_ls_wR_factor_ref 0.1460 _refine_ls_wR_factor_gt 0.1399 _refine_ls_goodness_of_fit_ref 1.130 _refine_ls_restrained_S_all 1.135 _refine_ls_shift/su_max 0.001 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group Tb1 Tb 0.23663(3) 0.52593(3) 0.00502(2) 0.01558(12) Uani 1 1 d U . . C1 C 0.7119(8) -0.2096(7) 0.8411(6) 0.0258(16) Uani 1 1 d U . . C2 C 0.9018(9) -0.1004(9) 0.5827(7) 0.052(3) Uani 1 1 d U . . H2AA H 0.9878 -0.1244 0.5568 0.062 Uiso 1 1 calc R . . C3 C 0.8760(8) -0.1685(8) 0.6891(6) 0.037(2) Uani 1 1 d U . . H3AA H 0.9439 -0.2354 0.7343 0.045 Uiso 1 1 calc R . . C4 C 0.7477(8) -0.1352(7) 0.7268(5) 0.0246(15) Uani 1 1 d U . . C5 C 0.6504(8) -0.0332(7) 0.6566(5) 0.0256(16) Uani 1 1 d U . . H5AA H 0.5625 -0.0092 0.6797 0.031 Uiso 1 1 calc R . . C6 C 0.6857(8) 0.0315(7) 0.5531(5) 0.0277(17) Uani 1 1 d U . . C7 C 0.5839(8) 0.1402(7) 0.4758(6) 0.0274(16) Uani 1 1 d U . . C8 C 0.6105(7) 0.2002(7) 0.3669(5) 0.0243(15) Uani 1 1 d U . . H8AA H 0.6953 0.1737 0.3406 0.029 Uiso 1 1 calc R . . C9 C 0.5115(7) 0.2985(7) 0.2985(5) 0.0233(15) Uani 1 1 d U . . C10 C 0.3851(8) 0.3359(8) 0.3391(6) 0.0359(19) Uani 1 1 d U . . H10A H 0.3149 0.4004 0.2944 0.043 Uiso 1 1 calc R . . C11 C 0.3672(9) 0.2739(8) 0.4483(6) 0.044(2) Uani 1 1 d U . . H11A H 0.2844 0.3010 0.4770 0.052 Uiso 1 1 calc R . . C12 C 0.5343(7) 0.3683(6) 0.1799(5) 0.0190(14) Uani 1 1 d U . . C13 C 0.2753(10) 0.7060(10) 0.1358(8) 0.053(2) Uani 1 1 d U . . H13A H 0.2350 0.6469 0.1893 0.063 Uiso 1 1 calc R . . C14 C 0.309(2) 0.7834(19) 0.2754(15) 0.171(9) Uani 1 1 d U . . H14A H 0.2164 0.8034 0.2969 0.257 Uiso 1 1 calc R . . H14B H 0.3591 0.8418 0.2829 0.257 Uiso 1 1 calc R . . H14C H 0.3538 0.6971 0.3206 0.257 Uiso 1 1 calc R . . C15 C 0.3652(18) 0.8906(12) 0.0809(12) 0.107(5) Uani 1 1 d U . . H15B H 0.4599 0.8793 0.1013 0.161 Uiso 1 1 calc R . . H15A H 0.3142 0.9741 0.0755 0.161 Uiso 1 1 calc R . . H15C H 0.3605 0.8830 0.0119 0.161 Uiso 1 1 calc R . . C16 C 0.0136(7) 0.4969(6) -0.1758(5) 0.0172(13) Uani 1 1 d U . . C17 C 0.0392(8) 0.5101(8) -0.4593(5) 0.0320(18) Uani 1 1 d U . . C18 C -0.0083(7) 0.4937(7) -0.3587(5) 0.0257(16) Uani 1 1 d U . . H18A H -0.0911 0.4686 -0.3393 0.031 Uiso 1 1 calc R . . C19 C 0.0655(8) 0.5141(7) -0.2861(5) 0.0256(16) Uani 1 1 d U . . C20 C 0.1855(9) 0.5542(9) -0.3192(6) 0.044(2) Uani 1 1 d U . . H20A H 0.2379 0.5707 -0.2725 0.053 Uiso 1 1 calc R . . C21 C 0.2273(10) 0.5696(11) -0.4239(7) 0.059(3) Uani 1 1 d U . . H21A H 0.3100 0.5944 -0.4448 0.071 Uiso 1 1 calc R . . N1 N 0.8088(7) -0.0016(7) 0.5150(5) 0.0450(19) Uani 1 1 d U . . N2 N 0.4631(7) 0.1764(7) 0.5157(5) 0.0381(17) Uani 1 1 d U . . N3 N 0.3081(10) 0.7957(9) 0.1601(8) 0.066(3) Uani 1 1 d U . . N4 N 0.1567(8) 0.5514(8) -0.4945(5) 0.049(2) Uani 1 1 d U . . O1 O 0.7958(5) -0.3146(5) 0.8934(4) 0.0263(11) Uani 1 1 d U . . O2 O 0.6035(6) -0.1643(5) 0.8767(4) 0.0418(15) Uani 1 1 d U . . O3 O 0.6560(5) 0.3523(5) 0.1495(4) 0.0244(11) Uani 1 1 d U . . O4 O 0.4307(5) 0.4419(5) 0.1211(3) 0.0252(11) Uani 1 1 d U . . O5 O -0.1048(5) 0.4743(5) -0.1570(3) 0.0236(11) Uani 1 1 d U . . O6 O 0.0901(5) 0.5055(5) -0.1096(4) 0.0258(11) Uani 1 1 d U . . O7 O 0.2922(5) 0.6938(5) 0.0527(4) 0.0312(12) Uani 1 1 d U . . O8 O 0.0517(5) 0.7164(5) -0.0616(4) 0.0311(12) Uani 1 1 d U . . H8C H -0.0040 0.7069 -0.1031 0.047 Uiso 1 1 d R . . H8D H 0.0055 0.7265 -0.0089 0.047 Uiso 1 1 d R . . O9 O 0.3933(5) 0.3749(5) -0.0603(4) 0.0282(12) Uani 1 1 d U . . H9A H 0.4638 0.4016 -0.0593 0.042 Uiso 1 1 d R . . H9B H 0.3903 0.3088 -0.0048 0.042 Uiso 1 1 d R . . O10 O 0.1741(13) 0.0927(12) 0.8082(9) 0.142(5) Uani 1 1 d U . . O11 O 0.0589(13) 0.1598(10) 0.9195(10) 0.140(5) Uani 1 1 d U . . H11C H 0.0224 0.1232 0.8872 0.210 Uiso 1 1 d R . . H11B H 0.1119 0.2011 0.8756 0.210 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 Tb1 0.01712(19) 0.01941(19) 0.00989(16) -0.00503(12) -0.00242(11) -0.00387(13) C1 0.028(4) 0.021(4) 0.023(3) -0.003(3) -0.007(3) -0.004(3) C2 0.030(4) 0.059(5) 0.040(4) 0.004(4) 0.005(4) 0.001(4) C3 0.026(4) 0.037(4) 0.029(4) 0.004(3) -0.003(3) 0.000(3) C4 0.030(4) 0.023(4) 0.020(3) -0.007(3) -0.003(3) -0.005(3) C5 0.027(4) 0.026(4) 0.020(3) -0.005(3) -0.001(3) -0.005(3) C6 0.030(4) 0.025(4) 0.020(3) 0.000(3) -0.003(3) -0.005(3) C7 0.025(4) 0.030(4) 0.023(3) -0.006(3) -0.002(3) -0.004(3) C8 0.025(4) 0.025(4) 0.020(3) -0.004(3) 0.002(3) -0.007(3) C9 0.025(4) 0.024(4) 0.017(3) -0.001(3) -0.002(3) -0.008(3) C10 0.034(4) 0.034(4) 0.023(3) 0.000(3) 0.001(3) 0.003(3) C11 0.036(4) 0.048(5) 0.028(4) -0.003(4) 0.004(3) 0.005(4) C12 0.023(3) 0.021(3) 0.015(3) -0.008(3) 0.003(2) -0.007(3) C13 0.059(6) 0.062(6) 0.057(5) -0.035(5) 0.012(4) -0.033(5) C14 0.232(17) 0.192(15) 0.169(14) -0.142(13) 0.000(12) -0.071(13) C15 0.160(13) 0.067(8) 0.125(11) -0.052(8) 0.015(10) -0.061(9) C16 0.020(3) 0.025(3) 0.012(3) -0.013(3) 0.002(2) -0.004(3) C17 0.034(4) 0.053(5) 0.019(3) -0.020(3) 0.002(3) -0.018(4) C18 0.020(3) 0.043(4) 0.019(3) -0.016(3) 0.002(3) -0.011(3) C19 0.028(4) 0.035(4) 0.020(3) -0.017(3) -0.001(3) -0.008(3) C20 0.043(5) 0.075(6) 0.031(4) -0.029(4) 0.007(3) -0.033(4) C21 0.054(5) 0.102(7) 0.046(5) -0.037(5) 0.013(4) -0.052(5) N1 0.034(4) 0.049(4) 0.028(3) 0.004(3) 0.003(3) 0.001(3) N2 0.035(4) 0.042(4) 0.022(3) -0.002(3) 0.005(3) 0.002(3) N3 0.083(6) 0.069(5) 0.076(5) -0.051(4) 0.020(4) -0.037(5) N4 0.047(4) 0.094(6) 0.029(3) -0.033(4) 0.011(3) -0.044(4) O1 0.023(3) 0.020(3) 0.027(2) -0.001(2) -0.005(2) 0.000(2) O2 0.044(3) 0.030(3) 0.029(3) 0.003(2) 0.008(2) 0.008(3) O3 0.025(3) 0.027(3) 0.017(2) -0.005(2) 0.0026(19) -0.003(2) O4 0.024(3) 0.035(3) 0.011(2) -0.002(2) -0.0071(18) -0.004(2) O5 0.027(3) 0.036(3) 0.014(2) -0.013(2) 0.0041(18) -0.015(2) O6 0.030(3) 0.032(3) 0.019(2) -0.014(2) -0.003(2) -0.007(2) O7 0.032(3) 0.038(3) 0.032(3) -0.023(2) 0.002(2) -0.007(2) O8 0.031(3) 0.028(3) 0.029(3) -0.007(2) -0.009(2) -0.002(2) O9 0.032(3) 0.030(3) 0.026(3) -0.011(2) 0.003(2) -0.013(2) O10 0.137(9) 0.142(10) 0.099(7) -0.030(7) -0.001(7) 0.032(8) O11 0.170(11) 0.108(8) 0.151(9) -0.068(7) -0.038(8) -0.006(8) _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 2.274(5) . ? Tb1 O4 2.316(6) . ? Tb1 O5 2.358(5) 2_565 ? Tb1 O3 2.376(5) 2_665 ? Tb1 O1 2.392(7) 2_656 ? Tb1 O8 2.417(7) . ? Tb1 O7 2.439(7) . ? Tb1 O9 2.452(6) . ? C1 O2 1.242(9) . ? C1 O1 1.268(8) . ? C1 C4 1.510(9) . ? C2 N1 1.338(11) . ? C2 C3 1.381(11) . ? C2 H2AA 0.9300 . ? C3 C4 1.375(11) . ? C3 H3AA 0.9300 . ? C4 C5 1.389(10) . ? C5 C6 1.370(9) . ? C5 H5AA 0.9300 . ? C6 N1 1.333(11) . ? C6 C7 1.484(10) . ? C7 N2 1.334(10) . ? C7 C8 1.393(9) . ? C8 C9 1.372(10) . ? C8 H8AA 0.9300 . ? C9 C10 1.388(11) . ? C9 C12 1.511(9) . ? C10 C11 1.379(10) . ? C10 H10A 0.9300 . ? C11 N2 1.345(10) . ? C11 H11A 0.9300 . ? C12 O4 1.253(8) . ? C12 O3 1.255(8) . ? C13 O7 1.167(10) . ? C13 N3 1.308(12) . ? C13 H13A 0.9300 . ? C14 N3 1.488(18) . ? C14 H14A 0.9600 . ? C14 H14B 0.9600 . ? C14 H14C 0.9600 . ? C15 N3 1.412(15) . ? C15 H15B 0.9600 . ? C15 H15A 0.9600 . ? C15 H15C 0.9600 . ? C16 O6 1.240(8) . ? C16 O5 1.260(8) . ? C16 C19 1.488(9) . ? C17 C18 1.358(9) . ? C17 N4 1.361(10) . ? C17 C17 1.482(13) 2_564 ? C18 C19 1.361(9) . ? C18 H18A 0.9300 . ? C19 C20 1.374(11) . ? C20 C21 1.392(12) . ? C20 H20A 0.9300 . ? C21 N4 1.307(11) . ? C21 H21A 0.9300 . ? O1 Tb1 2.392(7) 2_656 ? O3 Tb1 2.376(5) 2_665 ? O5 Tb1 2.358(5) 2_565 ? O8 H8C 0.8551 . ? O8 H8D 0.8500 . ? O9 H9A 0.8331 . ? O9 H9B 0.8436 . ? O11 H11C 0.8500 . ? O11 H11B 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 O6 Tb1 O4 150.1(2) . . ? O6 Tb1 O5 104.3(2) . 2_565 ? O4 Tb1 O5 87.6(2) . 2_565 ? O6 Tb1 O3 88.4(2) . 2_665 ? O4 Tb1 O3 96.5(2) . 2_665 ? O5 Tb1 O3 146.6(2) 2_565 2_665 ? O6 Tb1 O1 78.9(2) . 2_656 ? O4 Tb1 O1 79.63(19) . 2_656 ? O5 Tb1 O1 70.2(2) 2_565 2_656 ? O3 Tb1 O1 143.13(18) 2_665 2_656 ? O6 Tb1 O8 69.9(2) . . ? O4 Tb1 O8 140.0(2) . . ? O5 Tb1 O8 74.5(2) 2_565 . ? O3 Tb1 O8 81.5(2) 2_665 . ? O1 Tb1 O8 124.5(2) 2_656 . ? O6 Tb1 O7 139.05(19) . . ? O4 Tb1 O7 70.2(2) . . ? O5 Tb1 O7 75.18(19) 2_565 . ? O3 Tb1 O7 75.2(2) 2_665 . ? O1 Tb1 O7 134.5(2) 2_656 . ? O8 Tb1 O7 70.7(2) . . ? O6 Tb1 O9 79.7(2) . . ? O4 Tb1 O9 73.9(2) . . ? O5 Tb1 O9 139.70(18) 2_565 . ? O3 Tb1 O9 72.3(2) 2_665 . ? O1 Tb1 O9 71.4(2) 2_656 . ? O8 Tb1 O9 140.14(19) . . ? O7 Tb1 O9 127.6(2) . . ? O2 C1 O1 125.0(7) . . ? O2 C1 C4 118.2(6) . . ? O1 C1 C4 116.8(7) . . ? N1 C2 C3 123.1(8) . . ? N1 C2 H2AA 118.5 . . ? C3 C2 H2AA 118.5 . . ? C4 C3 C2 118.6(7) . . ? C4 C3 H3AA 120.7 . . ? C2 C3 H3AA 120.7 . . ? C3 C4 C5 118.6(6) . . ? C3 C4 C1 120.8(6) . . ? C5 C4 C1 120.6(7) . . ? C6 C5 C4 119.1(7) . . ? C6 C5 H5AA 120.4 . . ? C4 C5 H5AA 120.4 . . ? N1 C6 C5 122.8(7) . . ? N1 C6 C7 116.7(6) . . ? C5 C6 C7 120.5(7) . . ? N2 C7 C8 121.2(7) . . ? N2 C7 C6 116.4(6) . . ? C8 C7 C6 122.4(7) . . ? C9 C8 C7 119.9(7) . . ? C9 C8 H8AA 120.0 . . ? C7 C8 H8AA 120.0 . . ? C8 C9 C10 119.2(6) . . ? C8 C9 C12 122.6(7) . . ? C10 C9 C12 118.3(6) . . ? C11 C10 C9 117.6(7) . . ? C11 C10 H10A 121.2 . . ? C9 C10 H10A 121.2 . . ? N2 C11 C10 123.6(8) . . ? N2 C11 H11A 118.2 . . ? C10 C11 H11A 118.2 . . ? O4 C12 O3 125.5(6) . . ? O4 C12 C9 117.1(6) . . ? O3 C12 C9 117.3(6) . . ? O7 C13 N3 125.6(9) . . ? O7 C13 H13A 117.2 . . ? N3 C13 H13A 117.2 . . ? N3 C14 H14A 109.5 . . ? N3 C14 H14B 109.5 . . ? H14A C14 H14B 109.5 . . ? N3 C14 H14C 109.5 . . ? H14A C14 H14C 109.5 . . ? H14B C14 H14C 109.5 . . ? N3 C15 H15B 109.5 . . ? N3 C15 H15A 109.5 . . ? H15B C15 H15A 109.5 . . ? N3 C15 H15C 109.5 . . ? H15B C15 H15C 109.5 . . ? H15A C15 H15C 109.5 . . ? O6 C16 O5 125.1(6) . . ? O6 C16 C19 117.7(6) . . ? O5 C16 C19 117.2(6) . . ? C18 C17 N4 123.1(7) . . ? C18 C17 C17 121.3(8) . 2_564 ? N4 C17 C17 115.5(8) . 2_564 ? C17 C18 C19 119.9(7) . . ? C17 C18 H18A 120.0 . . ? C19 C18 H18A 120.0 . . ? C18 C19 C20 118.0(7) . . ? C18 C19 C16 120.1(6) . . ? C20 C19 C16 121.8(6) . . ? C19 C20 C21 118.8(8) . . ? C19 C20 H20A 120.6 . . ? C21 C20 H20A 120.6 . . ? N4 C21 C20 123.7(8) . . ? N4 C21 H21A 118.2 . . ? C20 C21 H21A 118.2 . . ? C6 N1 C2 117.8(7) . . ? C7 N2 C11 118.4(6) . . ? C13 N3 C15 119.7(10) . . ? C13 N3 C14 119.5(11) . . ? C15 N3 C14 119.9(11) . . ? C21 N4 C17 116.4(7) . . ? C1 O1 Tb1 132.2(5) . 2_656 ? C12 O3 Tb1 132.2(4) . 2_665 ? C12 O4 Tb1 163.8(5) . . ? C16 O5 Tb1 127.3(4) . 2_565 ? C16 O6 Tb1 177.2(5) . . ? C13 O7 Tb1 126.7(6) . . ? Tb1 O8 H8C 109.4 . . ? Tb1 O8 H8D 110.0 . . ? H8C O8 H8D 106.7 . . ? Tb1 O9 H9A 96.5 . . ? Tb1 O9 H9B 95.7 . . ? H9A O9 H9B 112.2 . . ? H11C O11 H11B 107.7 . . ? _diffrn_measured_fraction_theta_max 0.981 _diffrn_reflns_theta_full 27.48 _diffrn_measured_fraction_theta_full 0.981 _refine_diff_density_max 1.905 _refine_diff_density_min -1.803 _refine_diff_density_rms 0.210 data_shelxs4 _database_code_depnum_ccdc_archive 'CCDC 896130' #TrackingRef '4.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C21 H24 Dy N4 O11' _chemical_formula_weight 670.94 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' Dy Dy -0.1892 4.4098 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting triclinic _symmetry_space_group_name_H-M p-1 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 9.8856(16) _cell_length_b 11.6827(19) _cell_length_c 13.441(2) _cell_angle_alpha 66.863(4) _cell_angle_beta 86.995(4) _cell_angle_gamma 76.582(4) _cell_volume 1387.2(4) _cell_formula_units_Z 2 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 10443 _cell_measurement_theta_min 3.00 _cell_measurement_theta_max 27.49 _exptl_crystal_description ? _exptl_crystal_colour ? _exptl_crystal_size_max 0.80 _exptl_crystal_size_mid 0.30 _exptl_crystal_size_min 0.20 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.606 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 664 _exptl_absorpt_coefficient_mu 2.753 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.2168 _exptl_absorpt_correction_T_max 0.6090 _exptl_absorpt_process_details sadabs _exptl_special_details ; ? ; _diffrn_ambient_temperature 293(2) _diffrn_radiation_wavelength 0.71075 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type ? _diffrn_measurement_method ? _diffrn_detector_area_resol_mean ? _diffrn_standards_number . _diffrn_standards_interval_count . _diffrn_standards_interval_time . _diffrn_standards_decay_% . _diffrn_reflns_number 8628 _diffrn_reflns_av_R_equivalents 0.0390 _diffrn_reflns_av_sigmaI/netI 0.0587 _diffrn_reflns_limit_h_min -11 _diffrn_reflns_limit_h_max 11 _diffrn_reflns_limit_k_min -13 _diffrn_reflns_limit_k_max 13 _diffrn_reflns_limit_l_min -15 _diffrn_reflns_limit_l_max 15 _diffrn_reflns_theta_min 3.01 _diffrn_reflns_theta_max 25.01 _reflns_number_total 4834 _reflns_number_gt 4603 _reflns_threshold_expression >2sigma(I) _computing_data_collection ? _computing_cell_refinement ? _computing_data_reduction ? _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics ? _computing_publication_material ? _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0488P)^2^+59.9173P] 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 constra _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 4834 _refine_ls_number_parameters 336 _refine_ls_number_restraints 222 _refine_ls_R_factor_all 0.0855 _refine_ls_R_factor_gt 0.0824 _refine_ls_wR_factor_ref 0.1956 _refine_ls_wR_factor_gt 0.1938 _refine_ls_goodness_of_fit_ref 1.129 _refine_ls_restrained_S_all 1.116 _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 Dy1 Dy 0.23669(6) 1.02614(5) 0.00426(4) 0.0130(2) Uani 1 1 d U . . C1 C 0.2900(15) 0.7087(13) 0.1585(11) 0.030(3) Uani 1 1 d U . . C2 C 0.099(2) 0.6010(18) 0.4172(16) 0.055(5) Uani 1 1 d U . . H2 H 0.0128 0.6250 0.4432 0.066 Uiso 1 1 calc R . . C3 C 0.1210(15) 0.6695(14) 0.3121(12) 0.032(3) Uani 1 1 d U . . H3 H 0.0519 0.7369 0.2678 0.039 Uiso 1 1 calc R . . C4 C 0.2510(15) 0.6350(13) 0.2730(11) 0.028(3) Uani 1 1 d U . . C5 C 0.3495(15) 0.5341(14) 0.3425(12) 0.031(3) Uani 1 1 d U . . H5 H 0.4376 0.5099 0.3191 0.037 Uiso 1 1 calc R . . C6 C 0.3146(15) 0.4699(14) 0.4476(12) 0.033(3) Uani 1 1 d U . . C7 C 0.4197(14) 0.3579(14) 0.5267(11) 0.028(3) Uani 1 1 d U . . C8 C 0.3878(15) 0.2993(13) 0.6336(11) 0.027(3) Uani 1 1 d U . . H8 H 0.3012 0.3253 0.6582 0.032 Uiso 1 1 calc R . . C9 C 0.4885(14) 0.2011(13) 0.7022(11) 0.026(3) Uani 1 1 d U . . C10 C 0.6141(16) 0.1648(15) 0.6618(13) 0.036(3) Uani 1 1 d U . . H10 H 0.6837 0.0988 0.7068 0.044 Uiso 1 1 calc R . . C11 C 0.6359(18) 0.2280(17) 0.5527(14) 0.047(4) Uani 1 1 d U . . H11 H 0.7216 0.2040 0.5258 0.056 Uiso 1 1 calc R . . C12 C 0.4660(14) 0.1326(12) 0.8197(10) 0.022(3) Uani 1 1 d U . . C13 C 0.0146(14) 0.9942(13) -0.1734(10) 0.022(3) Uani 1 1 d U . . C14 C 0.229(2) 1.067(2) -0.4223(16) 0.060(5) Uani 1 1 d U . . H14 H 0.3122 1.0919 -0.4435 0.072 Uiso 1 1 calc R . . C15 C 0.1903(18) 1.0503(18) -0.3184(14) 0.045(4) Uani 1 1 d U . . H15 H 0.2445 1.0653 -0.2723 0.054 Uiso 1 1 calc R . . C16 C 0.0664(15) 1.0106(14) -0.2848(11) 0.028(3) Uani 1 1 d U . . C17 C -0.0101(15) 0.9925(14) -0.3586(11) 0.031(3) Uani 1 1 d U . . H17 H -0.0937 0.9675 -0.3398 0.037 Uiso 1 1 calc R . . C18 C 0.0392(15) 1.0120(15) -0.4600(11) 0.031(3) Uani 1 1 d U . . C19 C 0.273(2) 1.2083(19) 0.1366(17) 0.054(5) Uani 1 1 d U . . H19 H 0.2272 1.1529 0.1891 0.065 Uiso 1 1 calc R . . C20 C 0.373(4) 1.388(3) 0.081(3) 0.116(11) Uani 1 1 d U . . H20A H 0.4662 1.3762 0.1059 0.175 Uiso 1 1 calc R . . H20B H 0.3204 1.4722 0.0720 0.175 Uiso 1 1 calc R . . H20C H 0.3737 1.3783 0.0137 0.175 Uiso 1 1 calc R . . C21 C 0.290(4) 1.297(4) 0.268(3) 0.134(13) Uani 1 1 d U . . H21A H 0.2384 1.3806 0.2617 0.201 Uiso 1 1 calc R . . H21B H 0.3801 1.2798 0.3025 0.201 Uiso 1 1 calc R . . H21C H 0.2412 1.2342 0.3116 0.201 Uiso 1 1 calc R . . N1 N 0.1904(15) 0.5030(15) 0.4858(12) 0.049(4) Uani 1 1 d U . . N2 N 0.5373(14) 0.3228(13) 0.4845(10) 0.042(3) Uani 1 1 d U . . N3 N 0.1599(16) 1.0495(16) -0.4939(12) 0.051(4) Uani 1 1 d U . . N4 N 0.308(2) 1.2939(18) 0.1606(16) 0.067(5) Uani 1 1 d U . . O1 O 0.3963(12) 0.6638(11) 0.1235(9) 0.046(3) Uani 1 1 d U . . O2 O 0.2028(10) 0.8158(9) 0.1073(8) 0.029(2) Uani 1 1 d U . . O3 O 0.5692(10) 0.0585(10) 0.8788(8) 0.036(2) Uani 1 1 d U . . O4 O 0.3452(10) 0.1459(10) 0.8501(8) 0.033(2) Uani 1 1 d U . . O5 O -0.1040(10) 0.9730(10) -0.1556(8) 0.029(2) Uani 1 1 d U . . O6 O 0.0905(10) 1.0037(9) -0.1083(7) 0.028(2) Uani 1 1 d U . . O7 O 0.0534(11) 1.2154(10) -0.0626(8) 0.035(2) Uani 1 1 d U . . H1O7 H -0.0167 1.2314 -0.0268 0.042 Uiso 1 1 d R . . H2O7 H 0.0241 1.2061 -0.1167 0.042 Uiso 1 1 d R . . O8 O 0.3925(11) 0.8763(10) -0.0611(8) 0.033(2) Uani 1 1 d U . . H1O8 H 0.4795 0.8451 -0.0592 0.040 Uiso 1 1 d R . . H2O8 H 0.3529 0.8143 -0.0327 0.040 Uiso 1 1 d R . . O9 O 0.2929(11) 1.1919(10) 0.0521(9) 0.036(2) Uani 1 1 d U . . O10 O 0.171(3) 0.594(3) 0.809(2) 0.167(11) Uani 1 1 d U . . O11 O 0.947(3) 0.342(2) 0.077(2) 0.147(9) Uani 1 1 d U . . H11A H 0.9733 0.2933 0.1421 0.176 Uiso 1 1 d R . . H11B H 0.8650 0.3853 0.0776 0.176 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 Dy1 0.0133(3) 0.0172(3) 0.0067(3) -0.0015(2) 0.00060(19) -0.0059(2) C1 0.032(6) 0.026(6) 0.024(6) 0.000(5) -0.001(5) -0.009(5) C2 0.044(8) 0.052(8) 0.050(8) -0.005(6) 0.011(7) -0.003(6) C3 0.027(6) 0.036(7) 0.023(6) 0.000(5) 0.003(5) -0.007(5) C4 0.030(6) 0.025(6) 0.025(6) -0.005(5) 0.001(5) -0.009(5) C5 0.029(6) 0.030(6) 0.028(6) -0.006(5) 0.002(5) -0.006(5) C6 0.029(6) 0.032(6) 0.031(6) -0.004(5) 0.002(5) -0.010(5) C7 0.027(6) 0.031(6) 0.019(6) -0.006(5) 0.004(5) -0.005(5) C8 0.027(6) 0.032(6) 0.020(6) -0.008(5) 0.005(5) -0.008(5) C9 0.030(6) 0.027(6) 0.019(6) -0.006(5) 0.000(5) -0.008(5) C10 0.033(7) 0.034(7) 0.032(7) -0.005(5) -0.005(5) -0.003(5) C11 0.037(7) 0.054(8) 0.034(7) -0.008(6) 0.007(6) 0.000(6) C12 0.029(6) 0.019(5) 0.019(5) -0.006(5) 0.006(5) -0.009(5) C13 0.024(6) 0.028(6) 0.017(5) -0.013(5) 0.006(5) -0.007(5) C14 0.060(8) 0.079(9) 0.051(8) -0.027(7) 0.007(7) -0.033(7) C15 0.040(7) 0.064(8) 0.038(7) -0.024(6) 0.009(6) -0.021(6) C16 0.031(6) 0.035(6) 0.019(6) -0.009(5) 0.001(5) -0.008(5) C17 0.031(6) 0.040(7) 0.024(6) -0.015(5) 0.008(5) -0.010(5) C18 0.030(6) 0.042(7) 0.023(6) -0.015(5) 0.006(5) -0.013(5) C19 0.061(8) 0.054(8) 0.054(8) -0.026(7) 0.009(7) -0.020(7) C20 0.15(2) 0.102(16) 0.124(18) -0.062(14) 0.003(15) -0.047(14) C21 0.17(2) 0.15(2) 0.124(19) -0.084(16) 0.006(15) -0.050(16) N1 0.041(6) 0.052(7) 0.035(6) 0.000(5) 0.009(5) -0.004(6) N2 0.040(6) 0.043(6) 0.026(6) -0.001(5) 0.006(5) 0.000(5) N3 0.048(7) 0.079(8) 0.033(6) -0.022(6) 0.011(5) -0.031(6) N4 0.080(9) 0.068(8) 0.073(9) -0.040(7) 0.005(7) -0.031(7) O1 0.051(7) 0.035(6) 0.031(6) -0.001(5) 0.014(5) 0.005(5) O2 0.029(5) 0.028(5) 0.023(4) -0.003(4) 0.000(4) -0.007(4) O3 0.031(5) 0.041(5) 0.025(5) 0.001(4) -0.010(4) -0.012(4) O4 0.033(5) 0.032(5) 0.026(5) 0.000(4) 0.012(4) -0.016(4) O5 0.029(5) 0.039(5) 0.022(4) -0.014(4) 0.010(4) -0.015(4) O6 0.029(5) 0.037(5) 0.022(4) -0.014(4) -0.004(4) -0.009(4) O7 0.037(6) 0.042(6) 0.027(5) -0.018(5) 0.000(4) -0.001(5) O8 0.033(5) 0.031(5) 0.035(6) -0.008(4) 0.004(4) -0.014(4) O9 0.034(5) 0.042(5) 0.042(5) -0.026(4) 0.003(4) -0.012(4) O10 0.167(18) 0.169(18) 0.142(17) -0.061(14) 0.008(14) 0.005(14) O11 0.161(17) 0.122(15) 0.162(17) -0.073(13) -0.017(14) -0.005(13) _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 Dy1 O6 2.272(9) . ? Dy1 O3 2.311(9) 2_666 ? Dy1 O4 2.363(9) 1_564 ? Dy1 O5 2.364(9) 2_575 ? Dy1 O2 2.393(9) . ? Dy1 O7 2.394(10) . ? Dy1 O9 2.447(10) . ? Dy1 O8 2.454(10) . ? C1 O1 1.219(18) . ? C1 O2 1.292(17) . ? C1 C4 1.519(19) . ? C2 N1 1.32(2) . ? C2 C3 1.36(2) . ? C2 H2 0.9300 . ? C3 C4 1.40(2) . ? C3 H3 0.9300 . ? C4 C5 1.38(2) . ? C5 C6 1.38(2) . ? C5 H5 0.9300 . ? C6 N1 1.34(2) . ? C6 C7 1.52(2) . ? C7 N2 1.317(19) . ? C7 C8 1.382(19) . ? C8 C9 1.38(2) . ? C8 H8 0.9300 . ? C9 C10 1.37(2) . ? C9 C12 1.496(18) . ? C10 C11 1.39(2) . ? C10 H10 0.9300 . ? C11 N2 1.35(2) . ? C11 H11 0.9300 . ? C12 O4 1.237(16) . ? C12 O3 1.248(17) . ? C13 O6 1.236(16) . ? C13 O5 1.245(16) . ? C13 C16 1.510(18) . ? C14 N3 1.31(2) . ? C14 C15 1.38(3) . ? C14 H14 0.9300 . ? C15 C16 1.40(2) . ? C15 H15 0.9300 . ? C16 C17 1.38(2) . ? C17 C18 1.37(2) . ? C17 H17 0.9300 . ? C18 N3 1.36(2) . ? C18 C18 1.50(3) 2_574 ? C19 O9 1.22(2) . ? C19 N4 1.29(2) . ? C19 H19 0.9300 . ? C20 N4 1.44(3) . ? C20 H20A 0.9600 . ? C20 H20B 0.9600 . ? C20 H20C 0.9600 . ? C21 N4 1.47(4) . ? C21 H21A 0.9600 . ? C21 H21B 0.9600 . ? C21 H21C 0.9600 . ? O3 Dy1 2.311(9) 2_666 ? O4 Dy1 2.363(9) 1_546 ? O5 Dy1 2.364(9) 2_575 ? O7 H1O7 0.8500 . ? O7 H2O7 0.8501 . ? O8 H1O8 0.8500 . ? O8 H2O8 0.8499 . ? O11 H11A 0.8500 . ? O11 H11B 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 O6 Dy1 O3 149.4(4) . 2_666 ? O6 Dy1 O4 88.6(4) . 1_564 ? O3 Dy1 O4 96.9(4) 2_666 1_564 ? O6 Dy1 O5 104.8(3) . 2_575 ? O3 Dy1 O5 87.0(4) 2_666 2_575 ? O4 Dy1 O5 146.6(4) 1_564 2_575 ? O6 Dy1 O2 78.1(3) . . ? O3 Dy1 O2 79.6(3) 2_666 . ? O4 Dy1 O2 142.9(4) 1_564 . ? O5 Dy1 O2 70.5(3) 2_575 . ? O6 Dy1 O7 71.1(3) . . ? O3 Dy1 O7 139.4(4) 2_666 . ? O4 Dy1 O7 81.6(4) 1_564 . ? O5 Dy1 O7 74.4(3) 2_575 . ? O2 Dy1 O7 124.6(3) . . ? O6 Dy1 O9 140.3(4) . . ? O3 Dy1 O9 69.8(4) 2_666 . ? O4 Dy1 O9 76.1(4) 1_564 . ? O5 Dy1 O9 74.2(3) 2_575 . ? O2 Dy1 O9 133.9(4) . . ? O7 Dy1 O9 70.5(4) . . ? O6 Dy1 O8 78.3(3) . . ? O3 Dy1 O8 75.0(4) 2_666 . ? O4 Dy1 O8 71.8(3) 1_564 . ? O5 Dy1 O8 140.3(3) 2_575 . ? O2 Dy1 O8 71.6(3) . . ? O7 Dy1 O8 139.7(3) . . ? O9 Dy1 O8 128.2(3) . . ? O1 C1 O2 126.4(13) . . ? O1 C1 C4 119.2(13) . . ? O2 C1 C4 114.4(13) . . ? N1 C2 C3 125.6(17) . . ? N1 C2 H2 117.2 . . ? C3 C2 H2 117.2 . . ? C2 C3 C4 117.4(14) . . ? C2 C3 H3 121.3 . . ? C4 C3 H3 121.3 . . ? C5 C4 C3 118.7(13) . . ? C5 C4 C1 119.0(13) . . ? C3 C4 C1 122.2(13) . . ? C4 C5 C6 118.7(14) . . ? C4 C5 H5 120.6 . . ? C6 C5 H5 120.6 . . ? N1 C6 C5 122.9(14) . . ? N1 C6 C7 116.7(13) . . ? C5 C6 C7 120.4(13) . . ? N2 C7 C8 124.7(13) . . ? N2 C7 C6 114.9(12) . . ? C8 C7 C6 120.3(13) . . ? C9 C8 C7 117.8(13) . . ? C9 C8 H8 121.1 . . ? C7 C8 H8 121.1 . . ? C10 C9 C8 119.0(13) . . ? C10 C9 C12 118.7(12) . . ? C8 C9 C12 122.2(13) . . ? C9 C10 C11 119.1(14) . . ? C9 C10 H10 120.5 . . ? C11 C10 H10 120.5 . . ? N2 C11 C10 122.3(15) . . ? N2 C11 H11 118.8 . . ? C10 C11 H11 118.8 . . ? O4 C12 O3 124.3(12) . . ? O4 C12 C9 117.9(12) . . ? O3 C12 C9 117.6(12) . . ? O6 C13 O5 125.3(12) . . ? O6 C13 C16 118.6(12) . . ? O5 C13 C16 116.0(11) . . ? N3 C14 C15 126.0(18) . . ? N3 C14 H14 117.0 . . ? C15 C14 H14 117.0 . . ? C14 C15 C16 117.7(16) . . ? C14 C15 H15 121.1 . . ? C16 C15 H15 121.1 . . ? C17 C16 C15 117.9(13) . . ? C17 C16 C13 121.2(13) . . ? C15 C16 C13 120.9(13) . . ? C18 C17 C16 119.1(14) . . ? C18 C17 H17 120.4 . . ? C16 C17 H17 120.4 . . ? N3 C18 C17 123.9(14) . . ? N3 C18 C18 116.0(16) . 2_574 ? C17 C18 C18 120.0(16) . 2_574 ? O9 C19 N4 127(2) . . ? O9 C19 H19 116.5 . . ? N4 C19 H19 116.5 . . ? N4 C20 H20A 109.5 . . ? N4 C20 H20B 109.5 . . ? H20A C20 H20B 109.5 . . ? N4 C20 H20C 109.5 . . ? H20A C20 H20C 109.5 . . ? H20B C20 H20C 109.5 . . ? N4 C21 H21A 109.5 . . ? N4 C21 H21B 109.5 . . ? H21A C21 H21B 109.5 . . ? N4 C21 H21C 109.5 . . ? H21A C21 H21C 109.5 . . ? H21B C21 H21C 109.5 . . ? C2 N1 C6 116.7(15) . . ? C7 N2 C11 116.9(13) . . ? C14 N3 C18 115.4(15) . . ? C19 N4 C20 120(2) . . ? C19 N4 C21 122(2) . . ? C20 N4 C21 118(2) . . ? C1 O2 Dy1 131.5(9) . . ? C12 O3 Dy1 163.4(10) . 2_666 ? C12 O4 Dy1 133.4(9) . 1_546 ? C13 O5 Dy1 126.6(8) . 2_575 ? C13 O6 Dy1 177.0(9) . . ? Dy1 O7 H1O7 124.1 . . ? Dy1 O7 H2O7 99.2 . . ? H1O7 O7 H2O7 107.7 . . ? Dy1 O8 H1O8 137.3 . . ? Dy1 O8 H2O8 97.3 . . ? H1O8 O8 H2O8 107.7 . . ? C19 O9 Dy1 128.6(12) . . ? H11A O11 H11B 107.7 . . ? 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 N1 C2 C3 C4 -1(3) . . . . ? C2 C3 C4 C5 0(2) . . . . ? C2 C3 C4 C1 -176.9(16) . . . . ? O1 C1 C4 C5 14(2) . . . . ? O2 C1 C4 C5 -166.4(13) . . . . ? O1 C1 C4 C3 -169.2(15) . . . . ? O2 C1 C4 C3 10(2) . . . . ? C3 C4 C5 C6 1(2) . . . . ? C1 C4 C5 C6 178.1(13) . . . . ? C4 C5 C6 N1 -2(2) . . . . ? C4 C5 C6 C7 179.7(13) . . . . ? N1 C6 C7 N2 175.8(15) . . . . ? C5 C6 C7 N2 -5(2) . . . . ? N1 C6 C7 C8 -3(2) . . . . ? C5 C6 C7 C8 175.7(14) . . . . ? N2 C7 C8 C9 3(2) . . . . ? C6 C7 C8 C9 -178.0(13) . . . . ? C7 C8 C9 C10 -1(2) . . . . ? C7 C8 C9 C12 179.0(13) . . . . ? C8 C9 C10 C11 0(2) . . . . ? C12 C9 C10 C11 180.0(15) . . . . ? C9 C10 C11 N2 -1(3) . . . . ? C10 C9 C12 O4 -164.6(13) . . . . ? C8 C9 C12 O4 16(2) . . . . ? C10 C9 C12 O3 10(2) . . . . ? C8 C9 C12 O3 -169.5(13) . . . . ? N3 C14 C15 C16 1(3) . . . . ? C14 C15 C16 C17 -1(3) . . . . ? C14 C15 C16 C13 -178.3(16) . . . . ? O6 C13 C16 C17 175.6(13) . . . . ? O5 C13 C16 C17 -5(2) . . . . ? O6 C13 C16 C15 -7(2) . . . . ? O5 C13 C16 C15 172.0(14) . . . . ? C15 C16 C17 C18 1(2) . . . . ? C13 C16 C17 C18 178.2(14) . . . . ? C16 C17 C18 N3 -1(3) . . . . ? C16 C17 C18 C18 177.7(17) . . . 2_574 ? C3 C2 N1 C6 0(3) . . . . ? C5 C6 N1 C2 1(3) . . . . ? C7 C6 N1 C2 179.6(16) . . . . ? C8 C7 N2 C11 -4(2) . . . . ? C6 C7 N2 C11 176.9(15) . . . . ? C10 C11 N2 C7 3(3) . . . . ? C15 C14 N3 C18 0(3) . . . . ? C17 C18 N3 C14 0(3) . . . . ? C18 C18 N3 C14 -178.2(19) 2_574 . . . ? O9 C19 N4 C20 4(4) . . . . ? O9 C19 N4 C21 -174(3) . . . . ? O1 C1 O2 Dy1 -48(2) . . . . ? C4 C1 O2 Dy1 132.0(11) . . . . ? O6 Dy1 O2 C1 132.1(13) . . . . ? O3 Dy1 O2 C1 -26.9(12) 2_666 . . . ? O4 Dy1 O2 C1 60.8(14) 1_564 . . . ? O5 Dy1 O2 C1 -117.3(13) 2_575 . . . ? O7 Dy1 O2 C1 -171.0(11) . . . . ? O9 Dy1 O2 C1 -75.2(13) . . . . ? O8 Dy1 O2 C1 50.6(12) . . . . ? O4 C12 O3 Dy1 -93(3) . . . 2_666 ? C9 C12 O3 Dy1 93(3) . . . 2_666 ? O3 C12 O4 Dy1 -15(2) . . . 1_546 ? C9 C12 O4 Dy1 160.0(9) . . . 1_546 ? O6 C13 O5 Dy1 10(2) . . . 2_575 ? C16 C13 O5 Dy1 -169.7(9) . . . 2_575 ? O5 C13 O6 Dy1 -163(17) . . . . ? C16 C13 O6 Dy1 17(19) . . . . ? O3 Dy1 O6 C13 -95(18) 2_666 . . . ? O4 Dy1 O6 C13 6(18) 1_564 . . . ? O5 Dy1 O6 C13 155(18) 2_575 . . . ? O2 Dy1 O6 C13 -139(18) . . . . ? O7 Dy1 O6 C13 88(18) . . . . ? O9 Dy1 O6 C13 72(18) . . . . ? O8 Dy1 O6 C13 -66(18) . . . . ? N4 C19 O9 Dy1 177.3(16) . . . . ? O6 Dy1 O9 C19 111.3(15) . . . . ? O3 Dy1 O9 C19 -75.7(15) 2_666 . . . ? O4 Dy1 O9 C19 -178.5(16) 1_564 . . . ? O5 Dy1 O9 C19 17.0(15) 2_575 . . . ? O2 Dy1 O9 C19 -24.1(17) . . . . ? O7 Dy1 O9 C19 95.6(15) . . . . ? O8 Dy1 O9 C19 -125.7(15) . . . . ? _diffrn_measured_fraction_theta_max 0.989 _diffrn_reflns_theta_full 25.01 _diffrn_measured_fraction_theta_full 0.989 _refine_diff_density_max 7.069 _refine_diff_density_min -2.646 _refine_diff_density_rms 0.294 data_p120601k3 _database_code_depnum_ccdc_archive 'CCDC 896131' #TrackingRef '5.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C18 H20 Eu N5 O9' _chemical_formula_weight 602.35 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' Eu Eu -0.1578 3.6682 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting triclinic _symmetry_space_group_name_H-M P-1 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 9.2236(12) _cell_length_b 10.3657(13) _cell_length_c 12.8839(18) _cell_angle_alpha 75.576(11) _cell_angle_beta 69.469(13) _cell_angle_gamma 86.168(10) _cell_volume 1116.9(3) _cell_formula_units_Z 2 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 3598 _cell_measurement_theta_min 2.3937 _cell_measurement_theta_max 29.1949 _exptl_crystal_description ? _exptl_crystal_colour ? _exptl_crystal_size_max 0.08 _exptl_crystal_size_mid 0.06 _exptl_crystal_size_min 0.06 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.791 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 596 _exptl_absorpt_coefficient_mu 2.867 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.8031 _exptl_absorpt_correction_T_max 0.8468 _exptl_absorpt_process_details SADABS _exptl_special_details ; ? ; _diffrn_ambient_temperature 293(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type ? _diffrn_measurement_method ? _diffrn_detector_area_resol_mean ? _diffrn_standards_number . _diffrn_standards_interval_count . _diffrn_standards_interval_time . _diffrn_standards_decay_% . _diffrn_reflns_number 7917 _diffrn_reflns_av_R_equivalents 0.0577 _diffrn_reflns_av_sigmaI/netI 0.0778 _diffrn_reflns_limit_h_min -10 _diffrn_reflns_limit_h_max 10 _diffrn_reflns_limit_k_min -12 _diffrn_reflns_limit_k_max 12 _diffrn_reflns_limit_l_min -15 _diffrn_reflns_limit_l_max 15 _diffrn_reflns_theta_min 2.40 _diffrn_reflns_theta_max 25.01 _reflns_number_total 3932 _reflns_number_gt 3512 _reflns_threshold_expression >2sigma(I) _computing_data_collection ? _computing_cell_refinement ? _computing_data_reduction ? _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics ? _computing_publication_material ? _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.1087P)^2^+12.3900P] 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 3932 _refine_ls_number_parameters 302 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0751 _refine_ls_R_factor_gt 0.0683 _refine_ls_wR_factor_ref 0.1942 _refine_ls_wR_factor_gt 0.1854 _refine_ls_goodness_of_fit_ref 1.097 _refine_ls_restrained_S_all 1.097 _refine_ls_shift/su_max 0.001 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group Eu1 Eu 1.04426(6) 0.24917(5) 0.00197(4) 0.0168(2) Uani 1 1 d . . . C1 C 0.8631(13) 0.4453(10) 0.1849(9) 0.022(2) Uani 1 1 d . . . C2 C 0.5664(14) 0.4603(11) 0.4747(9) 0.026(3) Uani 1 1 d . . . C3 C 0.6493(12) 0.4939(10) 0.3569(8) 0.017(2) Uani 1 1 d . . . H3 H 0.6227 0.5677 0.3095 0.020 Uiso 1 1 calc R . . C4 C 0.7731(13) 0.4145(11) 0.3118(9) 0.022(2) Uani 1 1 d . . . C5 C 0.8111(16) 0.3085(14) 0.3848(11) 0.040(3) Uani 1 1 d . . . H5 H 0.8934 0.2546 0.3577 0.049 Uiso 1 1 calc R . . C6 C 0.723(2) 0.2841(15) 0.5000(11) 0.054(5) Uani 1 1 d . . . H6 H 0.7503 0.2125 0.5493 0.064 Uiso 1 1 calc R . . C7 C 1.0099(13) -0.0559(11) 0.1696(8) 0.021(2) Uani 1 1 d . . . C8 C 0.9688(12) -0.0398(10) 0.4704(8) 0.019(2) Uani 1 1 d . . . C9 C 1.0131(12) -0.0085(10) 0.3525(8) 0.017(2) Uani 1 1 d . . . H9 H 1.0776 0.0651 0.3088 0.020 Uiso 1 1 calc R . . C10 C 0.9605(14) -0.0880(11) 0.2998(9) 0.022(2) Uani 1 1 d . . . C11 C 0.8613(16) -0.1939(12) 0.3683(10) 0.031(3) Uani 1 1 d . . . H11 H 0.8224 -0.2484 0.3362 0.037 Uiso 1 1 calc R . . C12 C 0.8210(16) -0.2172(13) 0.4853(10) 0.034(3) Uani 1 1 d . . . H12 H 0.7531 -0.2881 0.5307 0.041 Uiso 1 1 calc R . . C13 C 0.6815(14) 0.1039(12) 0.1224(12) 0.033(3) Uani 1 1 d . . . H13 H 0.6791 0.1062 0.0504 0.040 Uiso 1 1 calc R . . C14 C 0.4245(17) 0.0091(17) 0.1950(18) 0.065(5) Uani 1 1 d . . . H14A H 0.4392 0.0273 0.1151 0.098 Uiso 1 1 calc R . . H14B H 0.3335 0.0527 0.2331 0.098 Uiso 1 1 calc R . . H14C H 0.4124 -0.0853 0.2272 0.098 Uiso 1 1 calc R . . C15 C 0.552(2) 0.052(2) 0.3235(15) 0.079(6) Uani 1 1 d . . . H15A H 0.6445 0.0916 0.3221 0.118 Uiso 1 1 calc R . . H15B H 0.5435 -0.0396 0.3651 0.118 Uiso 1 1 calc R . . H15C H 0.4637 0.0991 0.3601 0.118 Uiso 1 1 calc R . . C16 C 0.7639(14) 0.4420(11) -0.0891(11) 0.030(3) Uani 1 1 d . . . H16 H 0.7070 0.4774 -0.0276 0.037 Uiso 1 1 calc R . . C17 C 0.812(3) 0.427(2) -0.2787(15) 0.080(6) Uani 1 1 d . . . H17A H 0.8616 0.3467 -0.2542 0.120 Uiso 1 1 calc R . . H17B H 0.8879 0.4894 -0.3367 0.120 Uiso 1 1 calc R . . H17C H 0.7371 0.4066 -0.3090 0.120 Uiso 1 1 calc R . . C18 C 0.6133(17) 0.5796(15) -0.1957(12) 0.045(3) Uani 1 1 d . . . H18A H 0.5350 0.5369 -0.2095 0.067 Uiso 1 1 calc R . . H18B H 0.6575 0.6543 -0.2586 0.067 Uiso 1 1 calc R . . H18C H 0.5679 0.6097 -0.1268 0.067 Uiso 1 1 calc R . . N1 N 0.6027(14) 0.3564(12) 0.5454(8) 0.043(3) Uani 1 1 d . . . N2 N 0.8739(12) -0.1434(9) 0.5375(7) 0.026(2) Uani 1 1 d . . . N3 N 0.5611(12) 0.0594(11) 0.2096(10) 0.038(3) Uani 1 1 d . . . N4 N 0.7357(13) 0.4837(10) -0.1836(10) 0.035(2) Uani 1 1 d . . . N5 N 1.3764(14) 0.2395(11) -0.0475(11) 0.044(3) Uani 1 1 d . . . O1 O 0.8323(9) 0.5494(8) 0.1245(6) 0.0279(18) Uani 1 1 d . . . O2 O 0.9630(9) 0.3625(7) 0.1490(6) 0.0241(17) Uani 1 1 d . . . O3 O 1.0936(9) 0.0455(7) 0.1143(6) 0.0205(16) Uani 1 1 d . . . O4 O 0.9633(12) -0.1356(8) 0.1302(7) 0.035(2) Uani 1 1 d . . . O5 O 0.8045(9) 0.1454(8) 0.1291(7) 0.0330(19) Uani 1 1 d . . . O6 O 0.8599(14) 0.3595(9) -0.0757(10) 0.056(3) Uani 1 1 d . . . O7 O 1.2871(11) 0.2789(8) 0.0383(8) 0.039(2) Uani 1 1 d . . . O8 O 1.3197(10) 0.1973(8) -0.1069(8) 0.036(2) Uani 1 1 d . . . O9 O 1.5180(12) 0.2431(13) -0.0679(13) 0.076(4) 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 0.0196(3) 0.0201(3) 0.0121(3) -0.0092(2) -0.0038(2) 0.0024(2) C1 0.028(6) 0.018(5) 0.018(5) -0.007(4) -0.005(5) -0.005(5) C2 0.033(7) 0.029(6) 0.013(5) -0.008(4) -0.003(5) 0.014(5) C3 0.019(5) 0.019(5) 0.010(5) -0.006(4) -0.001(4) 0.002(4) C4 0.028(6) 0.024(6) 0.013(5) -0.010(4) -0.002(4) 0.000(5) C5 0.039(8) 0.042(8) 0.025(6) -0.009(5) 0.005(5) 0.021(6) C6 0.070(11) 0.050(9) 0.017(6) 0.003(6) 0.000(6) 0.038(8) C7 0.034(6) 0.023(6) 0.009(5) -0.010(4) -0.008(4) 0.010(5) C8 0.020(5) 0.023(5) 0.017(5) -0.012(4) -0.008(4) 0.009(4) C9 0.020(5) 0.019(5) 0.015(5) -0.010(4) -0.008(4) 0.004(4) C10 0.034(6) 0.024(6) 0.013(5) -0.008(4) -0.011(5) 0.005(5) C11 0.048(8) 0.028(6) 0.021(6) -0.008(5) -0.012(5) -0.012(6) C12 0.047(8) 0.037(7) 0.018(6) -0.003(5) -0.011(5) -0.017(6) C13 0.022(6) 0.025(6) 0.048(8) -0.005(5) -0.010(6) 0.001(5) C14 0.021(7) 0.054(10) 0.104(14) -0.009(9) -0.005(8) -0.004(7) C15 0.062(12) 0.099(16) 0.053(11) -0.014(10) 0.010(9) -0.021(11) C16 0.030(7) 0.023(6) 0.045(7) -0.008(5) -0.021(6) -0.007(5) C17 0.110(18) 0.098(15) 0.050(10) -0.034(10) -0.046(11) 0.038(13) C18 0.045(9) 0.053(9) 0.045(8) -0.019(7) -0.025(7) 0.023(7) N1 0.051(7) 0.050(7) 0.016(5) -0.007(5) -0.001(5) 0.027(6) N2 0.031(5) 0.032(5) 0.016(4) -0.011(4) -0.006(4) -0.001(4) N3 0.023(6) 0.039(6) 0.045(7) -0.008(5) -0.004(5) 0.002(5) N4 0.035(6) 0.031(6) 0.046(6) -0.010(5) -0.024(5) 0.007(5) N5 0.033(7) 0.038(7) 0.055(8) -0.001(6) -0.014(6) 0.000(5) O1 0.029(4) 0.026(4) 0.020(4) -0.003(3) 0.000(3) 0.001(3) O2 0.032(4) 0.022(4) 0.015(4) -0.011(3) 0.001(3) 0.003(3) O3 0.028(4) 0.019(4) 0.017(4) -0.002(3) -0.011(3) -0.002(3) O4 0.068(7) 0.027(4) 0.019(4) -0.009(3) -0.023(4) -0.003(4) O5 0.021(4) 0.038(5) 0.039(5) -0.010(4) -0.008(4) -0.002(4) O6 0.082(8) 0.025(5) 0.097(9) -0.010(5) -0.081(7) 0.011(5) O7 0.047(6) 0.027(5) 0.045(5) -0.011(4) -0.018(5) 0.001(4) O8 0.029(5) 0.032(5) 0.041(5) -0.011(4) -0.003(4) 0.006(4) O9 0.014(5) 0.074(8) 0.130(12) -0.008(7) -0.023(6) -0.006(5) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag Eu1 O4 2.321(7) 2_755 ? Eu1 O2 2.351(7) . ? Eu1 O6 2.358(8) . ? Eu1 O3 2.360(7) . ? Eu1 O5 2.373(8) . ? Eu1 O1 2.373(8) 2_765 ? Eu1 O7 2.496(10) . ? Eu1 O8 2.530(9) . ? Eu1 N5 2.902(12) . ? C1 O1 1.244(14) . ? C1 O2 1.262(14) . ? C1 C4 1.513(14) . ? C2 N1 1.334(15) . ? C2 C3 1.403(14) . ? C2 C2 1.47(2) 2_666 ? C3 C4 1.402(15) . ? C3 H3 0.9300 . ? C4 C5 1.371(17) . ? C5 C6 1.386(18) . ? C5 H5 0.9300 . ? C6 N1 1.340(17) . ? C6 H6 0.9300 . ? C7 O4 1.238(13) . ? C7 O3 1.248(13) . ? C7 C10 1.529(13) . ? C8 N2 1.341(15) . ? C8 C9 1.384(14) . ? C8 C8 1.510(19) 2_756 ? C9 C10 1.392(14) . ? C9 H9 0.9300 . ? C10 C11 1.381(16) . ? C11 C12 1.381(16) . ? C11 H11 0.9300 . ? C12 N2 1.347(15) . ? C12 H12 0.9300 . ? C13 O5 1.278(15) . ? C13 N3 1.281(17) . ? C13 H13 0.9300 . ? C14 N3 1.48(2) . ? C14 H14A 0.9600 . ? C14 H14B 0.9600 . ? C14 H14C 0.9600 . ? C15 N3 1.43(2) . ? C15 H15A 0.9600 . ? C15 H15B 0.9600 . ? C15 H15C 0.9600 . ? C16 O6 1.216(16) . ? C16 N4 1.298(16) . ? C16 H16 0.9300 . ? C17 N4 1.43(2) . ? C17 H17A 0.9600 . ? C17 H17B 0.9600 . ? C17 H17C 0.9600 . ? C18 N4 1.477(16) . ? C18 H18A 0.9600 . ? C18 H18B 0.9600 . ? C18 H18C 0.9600 . ? N5 O8 1.237(15) . ? N5 O9 1.240(15) . ? N5 O7 1.268(15) . ? O1 Eu1 2.373(8) 2_765 ? O4 Eu1 2.321(7) 2_755 ? 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 O4 Eu1 O2 160.9(3) 2_755 . ? O4 Eu1 O6 74.6(3) 2_755 . ? O2 Eu1 O6 90.9(3) . . ? O4 Eu1 O3 88.7(3) 2_755 . ? O2 Eu1 O3 96.1(3) . . ? O6 Eu1 O3 143.0(3) . . ? O4 Eu1 O5 89.3(3) 2_755 . ? O2 Eu1 O5 74.9(3) . . ? O6 Eu1 O5 75.7(4) . . ? O3 Eu1 O5 71.2(3) . . ? O4 Eu1 O1 99.5(3) 2_755 2_765 ? O2 Eu1 O1 88.0(3) . 2_765 ? O6 Eu1 O1 74.3(3) . 2_765 ? O3 Eu1 O1 142.0(3) . 2_765 ? O5 Eu1 O1 145.1(3) . 2_765 ? O4 Eu1 O7 122.5(3) 2_755 . ? O2 Eu1 O7 76.4(3) . . ? O6 Eu1 O7 144.6(3) . . ? O3 Eu1 O7 72.0(3) . . ? O5 Eu1 O7 129.9(3) . . ? O1 Eu1 O7 72.4(3) 2_765 . ? O4 Eu1 O8 72.1(3) 2_755 . ? O2 Eu1 O8 126.9(3) . . ? O6 Eu1 O8 127.1(4) . . ? O3 Eu1 O8 75.5(3) . . ? O5 Eu1 O8 142.1(3) . . ? O1 Eu1 O8 72.1(3) 2_765 . ? O7 Eu1 O8 50.9(3) . . ? O4 Eu1 N5 97.1(4) 2_755 . ? O2 Eu1 N5 101.9(3) . . ? O6 Eu1 N5 140.6(4) . . ? O3 Eu1 N5 73.0(3) . . ? O5 Eu1 N5 143.4(3) . . ? O1 Eu1 N5 69.2(3) 2_765 . ? O7 Eu1 N5 25.8(3) . . ? O8 Eu1 N5 25.1(3) . . ? O1 C1 O2 125.4(10) . . ? O1 C1 C4 117.5(10) . . ? O2 C1 C4 117.1(9) . . ? N1 C2 C3 122.2(10) . . ? N1 C2 C2 117.2(12) . 2_666 ? C3 C2 C2 120.7(12) . 2_666 ? C4 C3 C2 118.9(9) . . ? C4 C3 H3 120.6 . . ? C2 C3 H3 120.6 . . ? C5 C4 C3 118.8(10) . . ? C5 C4 C1 120.6(10) . . ? C3 C4 C1 120.6(10) . . ? C4 C5 C6 118.1(11) . . ? C4 C5 H5 121.0 . . ? C6 C5 H5 121.0 . . ? N1 C6 C5 124.5(12) . . ? N1 C6 H6 117.7 . . ? C5 C6 H6 117.7 . . ? O4 C7 O3 126.9(9) . . ? O4 C7 C10 115.7(10) . . ? O3 C7 C10 117.4(9) . . ? N2 C8 C9 122.6(9) . . ? N2 C8 C8 116.6(11) . 2_756 ? C9 C8 C8 120.8(12) . 2_756 ? C8 C9 C10 119.6(10) . . ? C8 C9 H9 120.2 . . ? C10 C9 H9 120.2 . . ? C11 C10 C9 118.2(9) . . ? C11 C10 C7 121.5(9) . . ? C9 C10 C7 120.3(10) . . ? C12 C11 C10 118.6(10) . . ? C12 C11 H11 120.7 . . ? C10 C11 H11 120.7 . . ? N2 C12 C11 123.9(11) . . ? N2 C12 H12 118.0 . . ? C11 C12 H12 118.0 . . ? O5 C13 N3 123.5(13) . . ? O5 C13 H13 118.2 . . ? N3 C13 H13 118.2 . . ? N3 C14 H14A 109.5 . . ? N3 C14 H14B 109.5 . . ? H14A C14 H14B 109.5 . . ? N3 C14 H14C 109.5 . . ? H14A C14 H14C 109.5 . . ? H14B C14 H14C 109.5 . . ? N3 C15 H15A 109.5 . . ? N3 C15 H15B 109.5 . . ? H15A C15 H15B 109.5 . . ? N3 C15 H15C 109.5 . . ? H15A C15 H15C 109.5 . . ? H15B C15 H15C 109.5 . . ? O6 C16 N4 124.2(13) . . ? O6 C16 H16 117.9 . . ? N4 C16 H16 117.9 . . ? N4 C17 H17A 109.5 . . ? N4 C17 H17B 109.5 . . ? H17A C17 H17B 109.5 . . ? N4 C17 H17C 109.5 . . ? H17A C17 H17C 109.5 . . ? H17B C17 H17C 109.5 . . ? N4 C18 H18A 109.5 . . ? N4 C18 H18B 109.5 . . ? H18A C18 H18B 109.5 . . ? N4 C18 H18C 109.5 . . ? H18A C18 H18C 109.5 . . ? H18B C18 H18C 109.5 . . ? C2 N1 C6 117.5(10) . . ? C8 N2 C12 117.0(9) . . ? C13 N3 C15 122.7(13) . . ? C13 N3 C14 120.3(13) . . ? C15 N3 C14 116.9(13) . . ? C16 N4 C17 120.6(12) . . ? C16 N4 C18 122.9(12) . . ? C17 N4 C18 116.1(12) . . ? O8 N5 O9 122.2(14) . . ? O8 N5 O7 119.2(11) . . ? O9 N5 O7 118.6(14) . . ? O8 N5 Eu1 60.4(6) . . ? O9 N5 Eu1 176.2(11) . . ? O7 N5 Eu1 58.9(7) . . ? C1 O1 Eu1 139.6(8) . 2_765 ? C1 O2 Eu1 139.8(7) . . ? C7 O3 Eu1 131.3(7) . . ? C7 O4 Eu1 158.4(8) . 2_755 ? C13 O5 Eu1 137.6(9) . . ? C16 O6 Eu1 157.2(9) . . ? N5 O7 Eu1 95.3(7) . . ? N5 O8 Eu1 94.5(7) . . ? _diffrn_measured_fraction_theta_max 0.999 _diffrn_reflns_theta_full 25.01 _diffrn_measured_fraction_theta_full 0.999 _refine_diff_density_max 7.156 _refine_diff_density_min -1.707 _refine_diff_density_rms 0.299 data_shelxs5 _database_code_depnum_ccdc_archive 'CCDC 896132' #TrackingRef '6.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C18 H20 Gd N5 O9' _chemical_formula_weight 607.64 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0000 0.0000 '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' Gd Gd 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M C2/c loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y, -z+1/2' 'x+1/2, y+1/2, z' '-x+1/2, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y, z-1/2' '-x+1/2, -y+1/2, -z' 'x+1/2, -y+1/2, z-1/2' _cell_length_a 24.529(2) _cell_length_b 9.3582(8) _cell_length_c 10.3822(9) _cell_angle_alpha 90.00 _cell_angle_beta 97.236(2) _cell_angle_gamma 90.00 _cell_volume 2364.2(3) _cell_formula_units_Z 4 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 8856 _cell_measurement_theta_min 3.12 _cell_measurement_theta_max 27.48 _exptl_crystal_description ? _exptl_crystal_colour ? _exptl_crystal_size_max 0.08 _exptl_crystal_size_mid 0.06 _exptl_crystal_size_min 0.06 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.707 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1196 _exptl_absorpt_coefficient_mu 2.861 _exptl_absorpt_correction_type MULTI-SCAN _exptl_absorpt_correction_T_min 0.8034 _exptl_absorpt_correction_T_max 0.8471 _exptl_absorpt_process_details SADABS _exptl_special_details ; ? ; _diffrn_ambient_temperature 293(2) _diffrn_radiation_wavelength 0.71075 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type ? _diffrn_measurement_method ? _diffrn_detector_area_resol_mean ? _diffrn_standards_number . _diffrn_standards_interval_count . _diffrn_standards_interval_time . _diffrn_standards_decay_% . _diffrn_reflns_number 8851 _diffrn_reflns_av_R_equivalents 0.0335 _diffrn_reflns_av_sigmaI/netI 0.0308 _diffrn_reflns_limit_h_min -31 _diffrn_reflns_limit_h_max 31 _diffrn_reflns_limit_k_min -12 _diffrn_reflns_limit_k_max 12 _diffrn_reflns_limit_l_min -13 _diffrn_reflns_limit_l_max 11 _diffrn_reflns_theta_min 3.13 _diffrn_reflns_theta_max 27.48 _reflns_number_total 2702 _reflns_number_gt 2566 _reflns_threshold_expression >2sigma(I) _computing_data_collection ? _computing_cell_refinement ? _computing_data_reduction ? _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics ? _computing_publication_material ? _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0443P)^2^+5.0147P] 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 CONSTRA _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 2702 _refine_ls_number_parameters 174 _refine_ls_number_restraints 70 _refine_ls_R_factor_all 0.0358 _refine_ls_R_factor_gt 0.0330 _refine_ls_wR_factor_ref 0.0864 _refine_ls_wR_factor_gt 0.0850 _refine_ls_goodness_of_fit_ref 1.102 _refine_ls_restrained_S_all 1.093 _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 Gd1 Gd 0.0000 0.48629(3) 0.2500 0.03245(11) Uani 1 2 d S . . C1 C 0.23282(14) 0.2957(5) 0.5368(4) 0.0415(9) Uani 1 1 d . . . C2 C 0.17809(13) 0.3212(4) 0.4929(4) 0.0370(8) Uani 1 1 d . . . H2AA H 0.1624 0.2823 0.4145 0.044 Uiso 1 1 calc R . . C3 C 0.14690(15) 0.4038(5) 0.5649(4) 0.0441(9) Uani 1 1 d . . . C4 C 0.1718(2) 0.4605(7) 0.6802(6) 0.0769(19) Uani 1 1 d . . . H4AA H 0.1519 0.5154 0.7325 0.092 Uiso 1 1 calc R . . C5 C 0.2272(2) 0.4335(9) 0.7164(6) 0.095(3) Uani 1 1 d . . . H5AA H 0.2442 0.4743 0.7928 0.114 Uiso 1 1 calc R . . C6 C 0.08699(15) 0.4304(5) 0.5198(4) 0.0471(10) Uani 1 1 d . . . C7 C -0.0546(3) 0.7860(7) 0.1015(7) 0.093(2) Uani 1 1 d . A . H7AA H -0.0219 0.8185 0.0752 0.111 Uiso 1 1 calc R . . C8 C -0.0804(10) 1.0138(18) -0.003(2) 0.119(2) Uani 0.537(11) 1 d PDU A 1 C8' C -0.1149(10) 0.960(2) -0.052(2) 0.119(2) Uani 0.463(11) 1 d PDU A 2 C9 C -0.1482(7) 0.8365(18) 0.1292(18) 0.1197(19) Uani 0.537(11) 1 d PDU A 1 C9' C -0.1479(8) 0.799(2) 0.025(2) 0.1196(19) Uani 0.463(11) 1 d PDU A 2 N1 N 0.25749(14) 0.3522(5) 0.6474(4) 0.0712(14) Uani 1 1 d . . . N2 N -0.0997(3) 0.8622(8) 0.0615(7) 0.1186(18) Uani 1 1 d DU . . N3 N -0.0159(8) 0.1827(12) 0.254(4) 0.102(9) Uani 0.50 1 d P . . O1 O 0.07093(11) 0.4022(4) 0.4046(3) 0.0606(9) Uani 1 1 d . . . O2 O 0.05825(16) 0.4778(5) 0.5986(4) 0.0771(13) Uani 1 1 d . . . O3 O -0.0289(3) 0.2469(6) 0.3184(5) 0.110(2) Uani 1 1 d . . . O4 O -0.05172(19) 0.6860(5) 0.1642(5) 0.0990(15) Uani 1 1 d . . . O5 O 0.0000 0.0499(12) 0.2500 0.354(14) Uani 1 2 d S . . 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 Gd1 0.01880(14) 0.04139(17) 0.03722(17) 0.000 0.00369(10) 0.000 C1 0.0225(16) 0.056(2) 0.045(2) -0.0086(18) 0.0004(15) 0.0058(15) C2 0.0250(16) 0.052(2) 0.0339(19) -0.0023(15) 0.0015(14) 0.0043(15) C3 0.0258(17) 0.063(3) 0.043(2) -0.0070(18) 0.0010(15) 0.0106(16) C4 0.037(2) 0.126(5) 0.066(4) -0.045(3) -0.003(2) 0.026(3) C5 0.041(3) 0.162(6) 0.076(4) -0.071(4) -0.019(3) 0.032(4) C6 0.0266(18) 0.072(3) 0.043(2) -0.001(2) 0.0035(16) 0.0151(18) C7 0.112(5) 0.071(4) 0.092(5) 0.003(3) 0.006(4) 0.045(4) C8 0.120(2) 0.118(2) 0.119(2) 0.0013(13) 0.0140(13) 0.0022(13) C8' 0.120(2) 0.118(2) 0.119(2) 0.0010(13) 0.0142(13) 0.0023(13) C9 0.120(2) 0.119(2) 0.120(2) 0.0007(13) 0.0144(13) 0.0026(13) C9' 0.120(2) 0.119(2) 0.120(2) 0.0003(13) 0.0142(13) 0.0025(13) N1 0.0318(18) 0.115(4) 0.062(3) -0.041(3) -0.0093(17) 0.021(2) N2 0.1196(19) 0.1174(19) 0.1186(19) 0.0005(8) 0.0141(8) 0.0032(8) N3 0.15(2) 0.051(6) 0.100(10) 0.013(10) -0.01(2) -0.029(8) O1 0.0342(15) 0.095(3) 0.0496(19) -0.0117(17) -0.0061(13) 0.0261(16) O2 0.0341(18) 0.147(4) 0.052(2) -0.011(2) 0.0123(16) 0.0314(18) O3 0.159(6) 0.086(4) 0.079(4) 0.030(3) -0.008(4) -0.049(4) O4 0.099(3) 0.069(3) 0.126(4) 0.035(3) 0.005(3) 0.032(2) O5 0.74(4) 0.046(5) 0.275(18) 0.000 0.05(2) 0.000 _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 Gd1 O2 2.278(4) 6_565 ? Gd1 O2 2.278(4) 5_566 ? Gd1 O1 2.349(3) 2 ? Gd1 O1 2.349(3) . ? Gd1 O4 2.368(4) 2 ? Gd1 O4 2.368(4) . ? Gd1 O3 2.481(5) 2 ? Gd1 O3 2.481(5) . ? Gd1 N3 2.869(11) 2 ? C1 N1 1.338(5) . ? C1 C2 1.383(5) . ? C1 C1 1.479(7) 7_556 ? C2 C3 1.373(5) . ? C2 H2AA 0.9300 . ? C3 C4 1.379(7) . ? C3 C6 1.506(5) . ? C4 C5 1.388(7) . ? C4 H4AA 0.9300 . ? C5 N1 1.332(6) . ? C5 H5AA 0.9300 . ? C6 O2 1.228(5) . ? C6 O1 1.239(5) . ? C7 O4 1.138(7) . ? C7 N2 1.338(9) . ? C7 H7AA 0.9300 . ? C8 N2 1.661(19) . ? C8' N2 1.50(2) . ? C9 N2 1.476(17) . ? C9' N2 1.33(2) . ? N3 N3 0.80(4) 2 ? N3 O3 0.98(3) . ? N3 O5 1.305(16) . ? N3 O3 1.53(2) 2 ? O2 Gd1 2.278(4) 5_566 ? O3 N3 1.53(2) 2 ? O5 N3 1.305(16) 2 ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag O2 Gd1 O2 163.1(2) 6_565 5_566 ? O2 Gd1 O1 93.02(13) 6_565 2 ? O2 Gd1 O1 92.63(13) 5_566 2 ? O2 Gd1 O1 92.63(13) 6_565 . ? O2 Gd1 O1 93.02(13) 5_566 . ? O1 Gd1 O1 140.88(19) 2 . ? O2 Gd1 O4 77.90(16) 6_565 2 ? O2 Gd1 O4 88.69(17) 5_566 2 ? O1 Gd1 O4 146.78(18) 2 2 ? O1 Gd1 O4 72.04(15) . 2 ? O2 Gd1 O4 88.69(17) 6_565 . ? O2 Gd1 O4 77.90(16) 5_566 . ? O1 Gd1 O4 72.04(15) 2 . ? O1 Gd1 O4 146.78(18) . . ? O4 Gd1 O4 75.8(3) 2 . ? O2 Gd1 O3 73.1(2) 6_565 2 ? O2 Gd1 O3 123.9(2) 5_566 2 ? O1 Gd1 O3 73.50(19) 2 2 ? O1 Gd1 O3 71.30(17) . 2 ? O4 Gd1 O3 131.4(2) 2 2 ? O4 Gd1 O3 139.81(19) . 2 ? O2 Gd1 O3 123.9(2) 6_565 . ? O2 Gd1 O3 73.1(2) 5_566 . ? O1 Gd1 O3 71.30(17) 2 . ? O1 Gd1 O3 73.50(19) . . ? O4 Gd1 O3 139.81(19) 2 . ? O4 Gd1 O3 131.4(2) . . ? O3 Gd1 O3 50.9(3) 2 . ? O2 Gd1 N3 92.1(6) 6_565 2 ? O2 Gd1 N3 104.8(6) 5_566 2 ? O1 Gd1 N3 75.4(6) 2 2 ? O1 Gd1 N3 65.7(7) . 2 ? O4 Gd1 N3 136.0(6) 2 2 ? O4 Gd1 N3 147.5(7) . 2 ? O3 Gd1 N3 19.4(6) 2 2 ? O3 Gd1 N3 32.3(6) . 2 ? N1 C1 C2 122.0(4) . . ? N1 C1 C1 116.5(4) . 7_556 ? C2 C1 C1 121.5(4) . 7_556 ? C3 C2 C1 120.1(4) . . ? C3 C2 H2AA 119.9 . . ? C1 C2 H2AA 119.9 . . ? C2 C3 C4 118.2(4) . . ? C2 C3 C6 120.8(4) . . ? C4 C3 C6 120.9(4) . . ? C3 C4 C5 118.4(4) . . ? C3 C4 H4AA 120.8 . . ? C5 C4 H4AA 120.8 . . ? N1 C5 C4 123.5(5) . . ? N1 C5 H5AA 118.2 . . ? C4 C5 H5AA 118.2 . . ? O2 C6 O1 125.5(4) . . ? O2 C6 C3 118.2(4) . . ? O1 C6 C3 116.4(3) . . ? O4 C7 N2 127.2(8) . . ? O4 C7 H7AA 116.4 . . ? N2 C7 H7AA 116.4 . . ? C5 N1 C1 117.7(4) . . ? C9' N2 C7 121.4(11) . . ? C9' N2 C9 47.6(10) . . ? C7 N2 C9 116.7(9) . . ? C9' N2 C8' 85.4(14) . . ? C7 N2 C8' 133.0(11) . . ? C9 N2 C8' 109.8(12) . . ? C9' N2 C8 123.4(14) . . ? C7 N2 C8 108.3(10) . . ? C9 N2 C8 128.2(11) . . ? C8' N2 C8 38.8(11) . . ? N3 N3 O3 119(5) 2 . ? N3 N3 O5 72.3(8) 2 . ? O3 N3 O5 137(3) . . ? N3 N3 O3 34(3) 2 2 ? O3 N3 O3 114.2(13) . 2 ? O5 N3 O3 96.9(13) . 2 ? C6 O1 Gd1 134.9(3) . . ? C6 O2 Gd1 167.2(4) . 5_566 ? N3 O3 N3 27(2) . 2 ? N3 O3 Gd1 103.2(12) . . ? N3 O3 Gd1 88.0(7) 2 . ? C7 O4 Gd1 148.8(5) . . ? N3 O5 N3 35.5(16) . 2 ? _diffrn_measured_fraction_theta_max 0.997 _diffrn_reflns_theta_full 27.48 _diffrn_measured_fraction_theta_full 0.997 _refine_diff_density_max 1.213 _refine_diff_density_min -0.770 _refine_diff_density_rms 0.100 data_shelxs6 _database_code_depnum_ccdc_archive 'CCDC 896133' #TrackingRef '7.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C18 H20 N5 O9 Tb' _chemical_formula_weight 609.31 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 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 C2/c loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y, -z+1/2' 'x+1/2, y+1/2, z' '-x+1/2, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y, z-1/2' '-x+1/2, -y+1/2, -z' 'x+1/2, -y+1/2, z-1/2' _cell_length_a 24.481(2) _cell_length_b 9.3535(8) _cell_length_c 10.3669(9) _cell_angle_alpha 90.00 _cell_angle_beta 97.336(3) _cell_angle_gamma 90.00 _cell_volume 2354.4(3) _cell_formula_units_Z 4 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 8760 _cell_measurement_theta_min 6.13 _cell_measurement_theta_max 27.54 _exptl_crystal_description ? _exptl_crystal_colour ? _exptl_crystal_size_max 0.08 _exptl_crystal_size_mid 0.06 _exptl_crystal_size_min 0.06 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.719 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1200 _exptl_absorpt_coefficient_mu 3.060 _exptl_absorpt_correction_type MULTI-SCAN _exptl_absorpt_correction_T_min 0.7919 _exptl_absorpt_correction_T_max 0.8377 _exptl_absorpt_process_details SADABS _exptl_special_details ; ? ; _diffrn_ambient_temperature 293(2) _diffrn_radiation_wavelength 0.71075 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type ? _diffrn_measurement_method ? _diffrn_detector_area_resol_mean ? _diffrn_standards_number . _diffrn_standards_interval_count . _diffrn_standards_interval_time . _diffrn_standards_decay_% . _diffrn_reflns_number 8850 _diffrn_reflns_av_R_equivalents 0.0339 _diffrn_reflns_av_sigmaI/netI 0.0333 _diffrn_reflns_limit_h_min -31 _diffrn_reflns_limit_h_max 26 _diffrn_reflns_limit_k_min -12 _diffrn_reflns_limit_k_max 12 _diffrn_reflns_limit_l_min -13 _diffrn_reflns_limit_l_max 13 _diffrn_reflns_theta_min 3.13 _diffrn_reflns_theta_max 27.48 _reflns_number_total 2694 _reflns_number_gt 2562 _reflns_threshold_expression >2sigma(I) _computing_data_collection ? _computing_cell_refinement ? _computing_data_reduction ? _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics ? _computing_publication_material ? _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0945P)^2^+17.6902P] 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 CONSTRA _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 2694 _refine_ls_number_parameters 183 _refine_ls_number_restraints 276 _refine_ls_R_factor_all 0.0595 _refine_ls_R_factor_gt 0.0563 _refine_ls_wR_factor_ref 0.1528 _refine_ls_wR_factor_gt 0.1498 _refine_ls_goodness_of_fit_ref 1.114 _refine_ls_restrained_S_all 1.101 _refine_ls_shift/su_max 0.004 _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 0.0000 -0.01327(4) 0.2500 0.02921(18) Uani 1 2 d SU . . C1 C 0.0865(3) -0.0708(9) 0.5201(7) 0.0430(15) Uani 1 1 d U . . C2 C 0.1464(3) -0.0962(8) 0.5656(7) 0.0411(15) Uani 1 1 d U . . C3 C 0.1779(2) -0.1785(7) 0.4921(6) 0.0342(13) Uani 1 1 d U . . H3A H 0.1625 -0.2158 0.4125 0.041 Uiso 1 1 calc R . . C4 C 0.2323(3) -0.2047(8) 0.5380(6) 0.0385(14) Uani 1 1 d U . . C5 C 0.2575(3) -0.1477(9) 0.6488(7) 0.0502(19) Uani 1 1 d U . . H5A H 0.2947 -0.1638 0.6756 0.060 Uiso 1 1 calc R . . C6 C 0.2278(4) -0.0683(14) 0.7180(10) 0.076(3) Uani 1 1 d U . . H6A H 0.2448 -0.0314 0.7963 0.091 Uiso 1 1 calc R . . C7 C -0.0526(6) 0.2889(15) 0.0992(13) 0.0904(16) Uani 1 1 d DU . . C8 C -0.1489(10) 0.341(3) 0.125(3) 0.0910(17) Uani 0.531(16) 1 d PDU A 1 C9 C -0.0812(15) 0.513(3) -0.004(3) 0.0911(18) Uani 0.531(16) 1 d PDU A 1 C8' C -0.1494(12) 0.298(3) 0.012(3) 0.0910(17) Uani 0.469(16) 1 d PDU A 2 C9' C -0.1127(14) 0.460(4) -0.048(3) 0.0909(18) Uani 0.469(16) 1 d PDU A 2 N1 N 0.1716(4) -0.0357(12) 0.6811(11) 0.082(3) Uani 1 1 d U . . N2 N -0.0905(10) 0.373(3) 0.060(2) 0.0905(16) Uani 0.531(16) 1 d PDU A 1 N3 N 0.0000 -0.313(3) 0.2500 0.132(3) Uani 1 2 d SU . . N2' N -0.1107(12) 0.347(3) 0.063(3) 0.0905(16) Uani 0.469(16) 1 d PDU A 2 O1 O 0.0580(3) -0.0220(8) 0.5995(8) 0.071(2) Uani 1 1 d U . . O2 O 0.0705(2) -0.0960(7) 0.4051(5) 0.0564(15) Uani 1 1 d U . . O3 O -0.0516(3) 0.1865(10) 0.1654(9) 0.0905(16) Uani 1 1 d U A . O4 O -0.0306(5) -0.2547(13) 0.3171(12) 0.131(3) Uani 1 1 d U . . O5 O -0.0283(6) -0.4700(13) 0.2403(16) 0.133(3) Uani 1 1 d U . . 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 0.0167(2) 0.0392(3) 0.0317(3) 0.000 0.00306(16) 0.000 C1 0.030(3) 0.059(4) 0.041(3) 0.001(3) 0.005(3) 0.012(3) C2 0.026(3) 0.059(4) 0.038(3) -0.005(3) 0.003(3) 0.011(3) C3 0.023(3) 0.048(3) 0.032(3) -0.002(2) 0.002(2) 0.005(2) C4 0.028(3) 0.050(3) 0.037(3) -0.005(3) 0.002(3) 0.008(3) C5 0.021(3) 0.081(5) 0.046(4) -0.026(3) -0.008(3) 0.017(3) C6 0.050(5) 0.109(7) 0.064(5) -0.037(5) -0.008(4) 0.015(5) C7 0.0905(17) 0.0901(17) 0.0905(17) 0.0004(6) 0.0114(6) 0.0007(6) C8 0.0909(19) 0.0910(19) 0.0911(19) 0.0002(8) 0.0115(8) 0.0003(8) C9 0.091(2) 0.091(2) 0.091(2) 0.0003(9) 0.0115(9) 0.0002(9) C8' 0.0909(19) 0.0909(19) 0.0910(19) 0.0001(8) 0.0115(8) 0.0003(8) C9' 0.0909(19) 0.0908(19) 0.0909(19) 0.0002(8) 0.0115(8) 0.0002(8) N1 0.057(5) 0.115(6) 0.072(5) -0.032(5) -0.001(4) 0.020(5) N2 0.0906(17) 0.0903(17) 0.0906(17) 0.0002(6) 0.0115(6) 0.0005(6) N3 0.133(3) 0.131(3) 0.132(3) 0.000 0.0157(14) 0.000 N2' 0.0906(17) 0.0903(17) 0.0906(17) 0.0002(6) 0.0115(6) 0.0004(6) O1 0.034(3) 0.128(6) 0.053(4) -0.008(3) 0.013(3) 0.030(3) O2 0.037(3) 0.084(4) 0.045(3) -0.011(3) -0.005(2) 0.021(3) O3 0.0905(17) 0.0900(17) 0.0909(17) 0.0009(8) 0.0113(8) 0.0011(8) O4 0.131(3) 0.130(3) 0.131(3) 0.0007(7) 0.0163(10) -0.0005(7) O5 0.134(3) 0.132(3) 0.134(3) -0.0001(10) 0.0154(17) 0.0000(10) _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 O1 2.264(7) 5_556 ? Tb1 O1 2.264(7) 6 ? Tb1 O2 2.335(5) 2 ? Tb1 O2 2.335(5) . ? Tb1 O3 2.361(9) . ? Tb1 O3 2.361(9) 2 ? Tb1 O4 2.506(12) . ? Tb1 O4 2.506(12) 2 ? C1 O2 1.229(9) . ? C1 O1 1.231(10) . ? C1 C2 1.501(9) . ? C2 C3 1.386(9) . ? C2 N1 1.395(12) . ? C3 C4 1.377(9) . ? C3 H3A 0.9300 . ? C4 C5 1.343(9) . ? C4 C4 1.505(12) 7_546 ? C5 C6 1.314(11) . ? C5 H5A 0.9300 . ? C6 N1 1.412(13) . ? C6 H6A 0.9300 . ? C7 O3 1.177(15) . ? C7 N2 1.25(3) . ? C7 N2' 1.52(3) . ? C8 N2 1.69(3) . ? C9 N2 1.49(3) . ? C8' N2' 1.12(4) . ? C9' N2' 1.56(4) . ? N3 O4 1.213(14) . ? N3 O4 1.213(14) 2 ? N3 O5 1.62(2) . ? N3 O5 1.62(2) 2 ? O1 Tb1 2.264(7) 5_556 ? O5 O5 1.37(3) 2 ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag O1 Tb1 O1 163.2(4) 5_556 6 ? O1 Tb1 O2 92.8(3) 5_556 2 ? O1 Tb1 O2 92.7(2) 6 2 ? O1 Tb1 O2 92.7(2) 5_556 . ? O1 Tb1 O2 92.8(3) 6 . ? O2 Tb1 O2 141.3(3) 2 . ? O1 Tb1 O3 77.7(3) 5_556 . ? O1 Tb1 O3 89.0(3) 6 . ? O2 Tb1 O3 72.1(3) 2 . ? O2 Tb1 O3 146.2(3) . . ? O1 Tb1 O3 89.0(3) 5_556 2 ? O1 Tb1 O3 77.7(3) 6 2 ? O2 Tb1 O3 146.2(3) 2 2 ? O2 Tb1 O3 72.1(3) . 2 ? O3 Tb1 O3 75.4(4) . 2 ? O1 Tb1 O4 72.8(3) 5_556 . ? O1 Tb1 O4 124.0(3) 6 . ? O2 Tb1 O4 70.9(3) 2 . ? O2 Tb1 O4 74.4(3) . . ? O3 Tb1 O4 130.7(3) . . ? O3 Tb1 O4 140.8(4) 2 . ? O1 Tb1 O4 124.0(3) 5_556 2 ? O1 Tb1 O4 72.8(3) 6 2 ? O2 Tb1 O4 74.4(3) 2 2 ? O2 Tb1 O4 70.9(3) . 2 ? O3 Tb1 O4 140.8(4) . 2 ? O3 Tb1 O4 130.7(3) 2 2 ? O4 Tb1 O4 51.3(5) . 2 ? O2 C1 O1 125.6(7) . . ? O2 C1 C2 116.8(6) . . ? O1 C1 C2 117.5(7) . . ? C3 C2 N1 118.7(7) . . ? C3 C2 C1 120.4(6) . . ? N1 C2 C1 120.9(7) . . ? C4 C3 C2 119.4(6) . . ? C4 C3 H3A 120.3 . . ? C2 C3 H3A 120.3 . . ? C5 C4 C3 122.9(6) . . ? C5 C4 C4 116.0(7) . 7_546 ? C3 C4 C4 121.0(7) . 7_546 ? C6 C5 C4 117.7(7) . . ? C6 C5 H5A 121.1 . . ? C4 C5 H5A 121.1 . . ? C5 C6 N1 124.1(8) . . ? C5 C6 H6A 117.9 . . ? N1 C6 H6A 117.9 . . ? O3 C7 N2 131.7(17) . . ? O3 C7 N2' 112.4(15) . . ? N2 C7 N2' 20.3(15) . . ? C2 N1 C6 117.0(8) . . ? C7 N2 C9 123(2) . . ? C7 N2 C8 113(2) . . ? C9 N2 C8 121(2) . . ? O4 N3 O4 127(2) . 2 ? O4 N3 O5 98.7(11) . . ? O4 N3 O5 131.2(14) 2 . ? O4 N3 O5 131.2(14) . 2 ? O4 N3 O5 98.7(11) 2 2 ? O5 N3 O5 50.0(13) . 2 ? C8' N2' C7 133(3) . . ? C8' N2' C9' 89(3) . . ? C7 N2' C9' 111(2) . . ? C1 O1 Tb1 166.5(7) . 5_556 ? C1 O2 Tb1 136.1(5) . . ? C7 O3 Tb1 146.2(9) . . ? N3 O4 Tb1 90.9(13) . . ? O5 O5 N3 65.0(6) 2 . ? _diffrn_measured_fraction_theta_max 0.998 _diffrn_reflns_theta_full 27.48 _diffrn_measured_fraction_theta_full 0.998 _refine_diff_density_max 1.695 _refine_diff_density_min -3.360 _refine_diff_density_rms 0.210 data_shelxs7 _database_code_depnum_ccdc_archive 'CCDC 896134' #TrackingRef '8.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C18 H20 Dy N5 O9' _chemical_formula_weight 612.89 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' Dy Dy -0.1892 4.4098 '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 C2/c loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y, -z+1/2' 'x+1/2, y+1/2, z' '-x+1/2, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y, z-1/2' '-x+1/2, -y+1/2, -z' 'x+1/2, -y+1/2, z-1/2' _cell_length_a 24.402(3) _cell_length_b 9.3439(9) _cell_length_c 10.3469(11) _cell_angle_alpha 90.00 _cell_angle_beta 97.371(3) _cell_angle_gamma 90.00 _cell_volume 2339.7(4) _cell_formula_units_Z 4 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 8352 _cell_measurement_theta_min 3.00 _cell_measurement_theta_max 27.48 _exptl_crystal_description ? _exptl_crystal_colour ? _exptl_crystal_size_max 0.10 _exptl_crystal_size_mid 0.08 _exptl_crystal_size_min 0.08 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.740 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1204 _exptl_absorpt_coefficient_mu 3.250 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.7370 _exptl_absorpt_correction_T_max 0.7810 _exptl_absorpt_process_details sadabs _exptl_special_details ; ? ; _diffrn_ambient_temperature 293(2) _diffrn_radiation_wavelength 0.71075 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type ? _diffrn_measurement_method ? _diffrn_detector_area_resol_mean ? _diffrn_standards_number . _diffrn_standards_interval_count . _diffrn_standards_interval_time . _diffrn_standards_decay_% . _diffrn_reflns_number 8284 _diffrn_reflns_av_R_equivalents 0.0300 _diffrn_reflns_av_sigmaI/netI 0.0312 _diffrn_reflns_limit_h_min -31 _diffrn_reflns_limit_h_max 31 _diffrn_reflns_limit_k_min -12 _diffrn_reflns_limit_k_max 11 _diffrn_reflns_limit_l_min -13 _diffrn_reflns_limit_l_max 12 _diffrn_reflns_theta_min 3.00 _diffrn_reflns_theta_max 27.48 _reflns_number_total 2675 _reflns_number_gt 2585 _reflns_threshold_expression >2sigma(I) _computing_data_collection ? _computing_cell_refinement ? _computing_data_reduction ? _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics ? _computing_publication_material ? _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0305P)^2^+9.3164P] 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 constra _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 2675 _refine_ls_number_parameters 174 _refine_ls_number_restraints 126 _refine_ls_R_factor_all 0.0365 _refine_ls_R_factor_gt 0.0340 _refine_ls_wR_factor_ref 0.0768 _refine_ls_wR_factor_gt 0.0759 _refine_ls_goodness_of_fit_ref 1.114 _refine_ls_restrained_S_all 1.208 _refine_ls_shift/su_max 0.001 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group Dy1 Dy 0.0000 1.01310(3) 0.7500 0.02831(11) Uani 1 2 d SU . . C2 C 0.17754(16) 1.1784(5) 0.9929(4) 0.0326(9) Uani 1 1 d U . . H2 H 0.1616 1.2167 0.9140 0.039 Uiso 1 1 calc R . . O4 O 0.06999(13) 1.0956(5) 0.9045(4) 0.0548(10) Uani 1 1 d U . . C1 C 0.23275(17) 1.2042(5) 1.0374(4) 0.0365(10) Uani 1 1 d U . . C3 C 0.14656(17) 1.0963(5) 1.0658(5) 0.0383(10) Uani 1 1 d U . . C6 C 0.08608(18) 1.0698(6) 1.0201(5) 0.0419(11) Uani 1 1 d U . . C4 C 0.1714(2) 1.0406(8) 1.1818(6) 0.0679(18) Uani 1 1 d U . . H4 H 0.1513 0.9864 1.2347 0.082 Uiso 1 1 calc R . . N2 N 0.25764(17) 1.1483(6) 1.1486(5) 0.0629(14) Uani 1 1 d U . . C5 C 0.2270(2) 1.0674(9) 1.2175(7) 0.084(2) Uani 1 1 d U . . H5 H 0.2440 1.0266 1.2943 0.100 Uiso 1 1 calc R . . O3 O 0.05726(16) 1.0231(5) 1.1001(4) 0.0699(14) Uani 1 1 d U . . O2 O 0.0307(3) 1.2509(6) 0.6830(5) 0.0993(19) Uani 1 1 d U . . O5 O -0.0514(2) 0.8152(5) 0.6647(6) 0.0905(16) Uani 1 1 d U . . N1 N -0.0988(3) 0.6373(8) 0.5611(8) 0.098(2) Uani 1 1 d U . . C7 C -0.0538(3) 0.7142(8) 0.6023(7) 0.083(2) Uani 1 1 d U A . H7 H -0.0207 0.6818 0.5774 0.099 Uiso 1 1 calc R . . N3 N 0.0000 1.3143(13) 0.7500 0.127(4) Uani 1 2 d SU . . C8 C -0.0818(15) 0.487(2) 0.500(3) 0.145(11) Uani 0.56(4) 1 d PU A 1 C8' C -0.1163(17) 0.547(4) 0.452(3) 0.142(13) Uani 0.44(4) 1 d PU A 2 C9 C -0.1474(11) 0.699(3) 0.532(4) 0.163(13) Uani 0.56(4) 1 d PU A 1 C9' C -0.1471(11) 0.652(3) 0.639(4) 0.126(12) Uani 0.44(4) 1 d PU A 2 O1 O 0.0249(6) 1.4470(14) 0.757(2) 0.143(6) Uani 0.50 1 d PU . . 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 Dy1 0.01489(13) 0.03741(17) 0.03270(17) 0.000 0.00326(10) 0.000 C2 0.0196(18) 0.045(2) 0.033(2) 0.0036(18) 0.0027(16) -0.0044(16) O4 0.0284(16) 0.088(3) 0.045(2) 0.0115(19) -0.0073(15) -0.0248(17) C1 0.0217(19) 0.051(3) 0.036(2) 0.006(2) 0.0006(17) -0.0074(17) C3 0.0214(19) 0.058(3) 0.036(2) 0.005(2) 0.0037(17) -0.0101(18) C6 0.022(2) 0.060(3) 0.044(3) 0.002(2) 0.0037(19) -0.0137(19) C4 0.036(3) 0.105(4) 0.060(4) 0.038(3) -0.001(2) -0.024(3) N2 0.028(2) 0.098(4) 0.058(3) 0.036(3) -0.008(2) -0.020(2) C5 0.042(3) 0.131(6) 0.073(4) 0.057(4) -0.015(3) -0.026(3) O3 0.0297(18) 0.138(4) 0.044(2) 0.009(2) 0.0103(16) -0.032(2) O2 0.129(5) 0.088(4) 0.079(4) 0.037(3) 0.005(3) -0.036(3) O5 0.092(3) 0.064(3) 0.113(4) -0.029(3) 0.003(3) -0.030(3) N1 0.099(2) 0.097(2) 0.098(2) -0.0002(11) 0.0112(11) -0.0046(11) C7 0.098(5) 0.062(4) 0.086(5) -0.005(4) 0.003(4) -0.038(4) N3 0.172(9) 0.077(6) 0.128(8) 0.000 0.002(7) 0.000 C8 0.173(19) 0.076(11) 0.173(19) -0.044(11) -0.025(15) -0.035(11) C8' 0.15(2) 0.136(18) 0.126(18) -0.042(14) -0.013(14) -0.066(16) C9 0.128(16) 0.152(17) 0.20(2) -0.017(16) 0.002(15) -0.036(13) C9' 0.104(15) 0.135(18) 0.14(2) -0.026(14) 0.006(13) -0.034(12) O1 0.168(11) 0.076(6) 0.182(10) -0.002(8) 0.011(9) -0.035(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 Dy1 O3 2.242(4) 6_575 ? Dy1 O3 2.242(4) 5_577 ? Dy1 O4 2.316(3) . ? Dy1 O4 2.316(3) 2_556 ? Dy1 O5 2.342(4) . ? Dy1 O5 2.342(4) 2_556 ? Dy1 O2 2.472(5) . ? Dy1 O2 2.472(5) 2_556 ? C2 C3 1.369(6) . ? C2 C1 1.388(5) . ? C2 H2 0.9300 . ? O4 C6 1.234(6) . ? C1 N2 1.336(6) . ? C1 C1 1.486(8) 7_577 ? C3 C4 1.376(7) . ? C3 C6 1.511(6) . ? C6 O3 1.232(6) . ? C4 C5 1.382(8) . ? C4 H4 0.9300 . ? N2 C5 1.333(7) . ? C5 H5 0.9300 . ? O3 Dy1 2.242(4) 5_577 ? O2 N3 1.235(8) . ? O5 C7 1.141(8) . ? N1 C9 1.32(3) . ? N1 C7 1.336(9) . ? N1 C8' 1.43(3) . ? N1 C9' 1.52(3) . ? N1 C8 1.61(2) . ? C7 H7 0.9300 . ? N3 O2 1.235(8) 2_556 ? N3 O1 1.380(15) 2_556 ? N3 O1 1.380(15) . ? O1 O1 1.21(3) 2_556 ? 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 Dy1 O3 162.7(3) 6_575 5_577 ? O3 Dy1 O4 93.32(15) 6_575 . ? O3 Dy1 O4 92.43(14) 5_577 . ? O3 Dy1 O4 92.43(14) 6_575 2_556 ? O3 Dy1 O4 93.32(15) 5_577 2_556 ? O4 Dy1 O4 141.1(2) . 2_556 ? O3 Dy1 O5 88.35(19) 6_575 . ? O3 Dy1 O5 77.93(18) 5_577 . ? O4 Dy1 O5 146.56(19) . . ? O4 Dy1 O5 72.01(17) 2_556 . ? O3 Dy1 O5 77.93(18) 6_575 2_556 ? O3 Dy1 O5 88.35(19) 5_577 2_556 ? O4 Dy1 O5 72.01(17) . 2_556 ? O4 Dy1 O5 146.56(19) 2_556 2_556 ? O5 Dy1 O5 75.7(3) . 2_556 ? O3 Dy1 O2 72.7(2) 6_575 . ? O3 Dy1 O2 124.6(2) 5_577 . ? O4 Dy1 O2 70.80(16) . . ? O4 Dy1 O2 74.36(18) 2_556 . ? O5 Dy1 O2 140.4(2) . . ? O5 Dy1 O2 130.4(2) 2_556 . ? O3 Dy1 O2 124.6(2) 6_575 2_556 ? O3 Dy1 O2 72.7(2) 5_577 2_556 ? O4 Dy1 O2 74.36(18) . 2_556 ? O4 Dy1 O2 70.80(16) 2_556 2_556 ? O5 Dy1 O2 130.4(2) . 2_556 ? O5 Dy1 O2 140.4(2) 2_556 2_556 ? O2 Dy1 O2 52.0(3) . 2_556 ? C3 C2 C1 119.7(4) . . ? C3 C2 H2 120.1 . . ? C1 C2 H2 120.1 . . ? C6 O4 Dy1 135.9(3) . . ? N2 C1 C2 122.2(4) . . ? N2 C1 C1 116.7(5) . 7_577 ? C2 C1 C1 121.2(5) . 7_577 ? C2 C3 C4 118.7(4) . . ? C2 C3 C6 120.4(4) . . ? C4 C3 C6 120.9(4) . . ? O3 C6 O4 125.6(4) . . ? O3 C6 C3 117.8(4) . . ? O4 C6 C3 116.6(4) . . ? C3 C4 C5 118.2(5) . . ? C3 C4 H4 120.9 . . ? C5 C4 H4 120.9 . . ? C5 N2 C1 117.3(4) . . ? N2 C5 C4 123.9(5) . . ? N2 C5 H5 118.0 . . ? C4 C5 H5 118.0 . . ? C6 O3 Dy1 167.8(5) . 5_577 ? N3 O2 Dy1 92.6(6) . . ? C7 O5 Dy1 148.5(6) . . ? C9 N1 C7 121.1(14) . . ? C9 N1 C8' 85(2) . . ? C7 N1 C8' 135.9(16) . . ? C9 N1 C9' 48.8(15) . . ? C7 N1 C9' 116.5(12) . . ? C8' N1 C9' 107.4(18) . . ? C9 N1 C8 124.0(17) . . ? C7 N1 C8 110.5(14) . . ? C8' N1 C8 41.0(16) . . ? C9' N1 C8 122.8(16) . . ? O5 C7 N1 127.3(9) . . ? O5 C7 H7 116.3 . . ? N1 C7 H7 116.3 . . ? O2 N3 O2 122.7(12) . 2_556 ? O2 N3 O1 134.2(10) . 2_556 ? O2 N3 O1 99.5(9) 2_556 2_556 ? O2 N3 O1 99.5(9) . . ? O2 N3 O1 134.2(10) 2_556 . ? O1 N3 O1 51.9(14) 2_556 . ? O1 O1 N3 64.1(7) 2_556 . ? _diffrn_measured_fraction_theta_max 0.998 _diffrn_reflns_theta_full 27.48 _diffrn_measured_fraction_theta_full 0.998 _refine_diff_density_max 1.052 _refine_diff_density_min -0.998 _refine_diff_density_rms 0.102