# Supplementary Material (ESI) for CrystEngComm # This journal is (c) The Royal Society of Chemistry 2010 data_global _journal_name_full CrystEngComm _journal_coden_Cambridge 1350 _publ_contact_author_name 'Wu, Jian-Zhong' _publ_contact_author_email wujzh@scnu.edu.cn _publ_section_title ; Tuning the porosity of lanthanide MOFs with 2,5-pyrazinedicarboxylate and the first in situ hydrothermal carboxyl transfer ; loop_ _publ_author_name B.Cai P.Yang J.-W.Dai J.-Z.Wu # Attachment '- 1-Nd.cif' data_1-Nd _database_code_depnum_ccdc_archive 'CCDC 742763' #TrackingRef '- 1-Nd.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety '2(C7 H6 N2 O8 Nd), 10(H O0.50)' _chemical_formula_sum 'C14 H30 N4 Nd2 O25' _chemical_formula_weight 942.90 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' Nd Nd -0.1943 3.0179 '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' _symmetry_space_group_name_Hall '-P 1' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 6.1645(12) _cell_length_b 10.074(2) _cell_length_c 13.503(3) _cell_angle_alpha 68.951(2) _cell_angle_beta 80.872(2) _cell_angle_gamma 76.667(2) _cell_volume 758.8(3) _cell_formula_units_Z 1 _cell_measurement_temperature 298(2) _cell_measurement_reflns_used 3254 _cell_measurement_theta_min 2.26 _cell_measurement_theta_max 27.80 _exptl_crystal_description block _exptl_crystal_colour colorless _exptl_crystal_size_max 0.24 _exptl_crystal_size_mid 0.17 _exptl_crystal_size_min 0.11 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 2.063 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 462 _exptl_absorpt_coefficient_mu 3.488 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.4882 _exptl_absorpt_correction_T_max 0.7002 _exptl_absorpt_process_details 'SADABS, Bruker(2002)' _exptl_special_details ; ? ; _diffrn_ambient_temperature 298(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type ? _diffrn_measurement_method ? _diffrn_detector_area_resol_mean ? _diffrn_reflns_number 3822 _diffrn_reflns_av_R_equivalents 0.0188 _diffrn_reflns_av_sigmaI/netI 0.0329 _diffrn_reflns_limit_h_min -5 _diffrn_reflns_limit_h_max 7 _diffrn_reflns_limit_k_min -11 _diffrn_reflns_limit_k_max 12 _diffrn_reflns_limit_l_min -14 _diffrn_reflns_limit_l_max 16 _diffrn_reflns_theta_min 2.21 _diffrn_reflns_theta_max 25.20 _reflns_number_total 2660 _reflns_number_gt 2488 _reflns_threshold_expression >2sigma(I) _computing_data_collection ? _computing_cell_refinement ? _computing_data_reduction ? _computing_structure_solution 'SHELXS-97 (Sheldrick, 2008)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _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^)+(0.0593P)^2^+2.0212P] 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 2660 _refine_ls_number_parameters 208 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0360 _refine_ls_R_factor_gt 0.0338 _refine_ls_wR_factor_ref 0.0902 _refine_ls_wR_factor_gt 0.0887 _refine_ls_goodness_of_fit_ref 1.036 _refine_ls_restrained_S_all 1.036 _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 Nd1 Nd 0.82878(4) 0.61541(3) 0.196655(19) 0.02059(12) Uani 1 1 d . . . C1 C 1.2838(9) 0.7695(6) 0.1405(4) 0.0238(11) Uani 1 1 d . . . C2 C 1.1336(8) 0.8950(6) 0.0682(4) 0.0229(10) Uani 1 1 d . . . C3 C 0.8094(9) 0.9706(6) -0.0145(4) 0.0242(11) Uani 1 1 d . . . H3 H 0.6761 0.9531 -0.0268 0.029 Uiso 1 1 calc R . . C4 C 0.9469(10) 0.3842(6) 0.4409(4) 0.0303(12) Uani 1 1 d . . . C5 C 0.7102(9) 0.4451(6) 0.4730(4) 0.0281(11) Uani 1 1 d . . . C6 C 0.3836(9) 0.6012(6) 0.4225(4) 0.0308(12) Uani 1 1 d . . . H6 H 0.2984 0.6729 0.3707 0.037 Uiso 1 1 calc R . . C7 C 1.0873(9) 0.4403(6) 0.0338(4) 0.0272(11) Uani 1 1 d . . . N1 N 0.9402(7) 0.8659(5) 0.0544(3) 0.0235(9) Uani 1 1 d . . . N2 N 0.5924(8) 0.5457(5) 0.3946(3) 0.0297(10) Uani 1 1 d . . . O1 O 1.2121(7) 0.6543(4) 0.1846(3) 0.0353(9) Uani 1 1 d . . . O2 O 1.4738(6) 0.7876(4) 0.1496(3) 0.0287(8) Uani 1 1 d . . . O3 O 1.0118(7) 0.4309(5) 0.3438(3) 0.0355(9) Uani 1 1 d . . . O4 O 1.0647(8) 0.2925(6) 0.5114(3) 0.0498(13) Uani 1 1 d . . . O5 O 1.0829(7) 0.4308(4) 0.1289(3) 0.0356(10) Uani 1 1 d . . . O6 O 1.2206(7) 0.3631(4) -0.0122(3) 0.0319(9) Uani 1 1 d . . . O1W O 0.8209(8) 0.7932(5) 0.2858(3) 0.0420(11) Uani 1 1 d . . . H1W H 0.7112 0.8582 0.2815 0.063 Uiso 1 1 d R . . H2W H 0.8699 0.7814 0.3451 0.063 Uiso 1 1 d R . . O2W O 0.5842(7) 0.4363(4) 0.2197(3) 0.0369(9) Uani 1 1 d . . . H3W H 0.4524 0.4853 0.2117 0.055 Uiso 1 1 d R . . H4W H 0.5621 0.3632 0.2713 0.055 Uiso 1 1 d R . . O3W O 0.6347(11) 0.2865(9) 0.0806(6) 0.094(2) Uani 1 1 d . . . H5W H 0.6221 0.2059 0.1322 0.141 Uiso 1 1 d R . . H6W H 0.6869 0.2505 0.0302 0.141 Uiso 1 1 d R . . O4W O 0.5053(15) 0.2077(10) 0.4125(7) 0.113(3) Uani 1 1 d . . . H8W H 0.4566 0.1341 0.4610 0.170 Uiso 1 1 d R . . H7W H 0.6333 0.1611 0.3942 0.170 Uiso 1 1 d R . . O5W O 0.550(4) 0.0446(12) 0.2603(14) 0.302(13) Uani 1 1 d . . . H9W H 0.4938 -0.0117 0.3192 0.453 Uiso 1 1 d R . . H10W H 0.4288 0.1076 0.2408 0.453 Uiso 1 1 d R . . O6W O 0.077(3) 0.1227(14) 0.2671(13) 0.275(10) Uani 1 1 d . . . H12W H -0.0427 0.1315 0.2373 0.412 Uiso 1 1 d R . . H11W H 0.0803 0.2143 0.2479 0.412 Uiso 1 1 d R . . O7W O 0.104(5) 0.978(3) 0.508(3) 0.212(15) Uani 0.50 1 d P . . H14W H 0.1081 0.9724 0.5723 0.318 Uiso 0.50 1 d PR . . H13W H 0.2182 1.0072 0.4780 0.318 Uiso 0.50 1 d PR . . 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 Nd1 0.01821(18) 0.02542(18) 0.01474(17) -0.00229(12) -0.00239(11) -0.00408(11) C1 0.021(3) 0.031(3) 0.016(2) -0.004(2) 0.001(2) -0.006(2) C2 0.019(2) 0.029(3) 0.018(2) -0.005(2) -0.0010(19) -0.003(2) C3 0.016(3) 0.031(3) 0.021(3) -0.002(2) -0.006(2) -0.004(2) C4 0.033(3) 0.035(3) 0.021(3) -0.007(2) -0.004(2) -0.005(2) C5 0.030(3) 0.033(3) 0.018(3) -0.004(2) -0.002(2) -0.008(2) C6 0.026(3) 0.038(3) 0.019(3) 0.001(2) -0.003(2) -0.004(2) C7 0.026(3) 0.033(3) 0.020(3) -0.005(2) -0.005(2) -0.005(2) N1 0.017(2) 0.030(2) 0.020(2) -0.0030(18) -0.0035(17) -0.0064(17) N2 0.037(3) 0.031(2) 0.018(2) -0.0037(19) -0.0044(19) -0.006(2) O1 0.025(2) 0.030(2) 0.038(2) 0.0079(17) -0.0080(17) -0.0075(16) O2 0.0182(19) 0.033(2) 0.031(2) -0.0044(16) -0.0068(15) -0.0036(15) O3 0.030(2) 0.045(2) 0.0176(19) 0.0021(17) -0.0016(16) -0.0013(18) O4 0.044(3) 0.065(3) 0.022(2) -0.002(2) -0.0087(19) 0.010(2) O5 0.039(2) 0.042(2) 0.0199(19) -0.0101(17) -0.0097(17) 0.0086(18) O6 0.035(2) 0.035(2) 0.0255(19) -0.0140(17) -0.0080(16) 0.0038(17) O1W 0.059(3) 0.043(2) 0.024(2) -0.0115(18) -0.008(2) -0.007(2) O2W 0.034(2) 0.035(2) 0.040(2) -0.0078(18) -0.0040(18) -0.0104(18) O3W 0.066(4) 0.147(7) 0.094(5) -0.084(5) -0.014(4) 0.009(4) O4W 0.100(6) 0.117(6) 0.091(6) -0.014(5) 0.008(5) -0.003(5) O5W 0.53(3) 0.100(8) 0.29(2) -0.112(11) -0.26(2) 0.124(14) O6W 0.38(3) 0.116(10) 0.210(16) 0.029(10) -0.019(16) 0.048(13) O7W 0.22(4) 0.100(17) 0.30(4) -0.02(2) -0.12(3) 0.016(19) _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 Nd1 O3 2.401(4) . ? Nd1 O1 2.454(4) . ? Nd1 O2 2.470(4) 1_455 ? Nd1 O1W 2.479(4) . ? Nd1 O6 2.483(4) 2_765 ? Nd1 O5 2.485(4) . ? Nd1 O2W 2.515(4) . ? Nd1 N1 2.726(4) . ? Nd1 N2 2.766(5) . ? C1 O1 1.247(7) . ? C1 O2 1.257(7) . ? C1 C2 1.506(7) . ? C2 N1 1.347(7) . ? C2 C3 1.383(8) 2_775 ? C3 N1 1.330(7) . ? C3 H3 0.9300 . ? C4 O4 1.251(7) . ? C4 O3 1.256(7) . ? C4 C5 1.507(8) . ? C5 N2 1.344(7) . ? C5 C6 1.392(8) 2_666 ? C6 N2 1.333(7) . ? C6 C5 1.392(8) 2_666 ? C6 H6 0.9300 . ? C7 O6 1.248(7) . ? C7 O5 1.249(7) . ? C7 C7 1.537(10) 2_765 ? O2 Nd1 2.470(4) 1_655 ? O1W H1W 0.8189 . ? O1W H2W 0.8597 . ? O2W H3W 0.8484 . ? O2W H4W 0.8335 . ? O3W H5W 0.8690 . ? O3W H6W 0.8673 . ? O4W H8W 0.8722 . ? O4W H7W 0.8688 . ? O5W H9W 0.8683 . ? O5W H10W 0.8689 . ? O6W H12W 0.8676 . ? O6W H11W 0.8684 . ? O7W H14W 0.8552 . ? O7W H13W 0.8144 . ? 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 Nd1 O1 72.13(14) . . ? O3 Nd1 O2 142.54(13) . 1_455 ? O1 Nd1 O2 131.46(13) . 1_455 ? O3 Nd1 O1W 88.36(15) . . ? O1 Nd1 O1W 72.01(16) . . ? O2 Nd1 O1W 76.29(14) 1_455 . ? O3 Nd1 O6 135.22(13) . 2_765 ? O1 Nd1 O6 103.55(14) . 2_765 ? O2 Nd1 O6 74.02(13) 1_455 2_765 ? O1W Nd1 O6 133.92(13) . 2_765 ? O3 Nd1 O5 71.80(13) . . ? O1 Nd1 O5 72.37(15) . . ? O2 Nd1 O5 137.06(13) 1_455 . ? O1W Nd1 O5 143.09(16) . . ? O6 Nd1 O5 64.81(12) 2_765 . ? O3 Nd1 O2W 84.96(15) . . ? O1 Nd1 O2W 146.28(14) . . ? O2 Nd1 O2W 81.39(13) 1_455 . ? O1W Nd1 O2W 133.04(15) . . ? O6 Nd1 O2W 75.49(14) 2_765 . ? O5 Nd1 O2W 77.20(14) . . ? O3 Nd1 N1 132.41(14) . . ? O1 Nd1 N1 61.36(12) . . ? O2 Nd1 N1 73.42(13) 1_455 . ? O1W Nd1 N1 68.93(14) . . ? O6 Nd1 N1 69.29(13) 2_765 . ? O5 Nd1 N1 101.62(14) . . ? O2W Nd1 N1 141.00(13) . . ? O3 Nd1 N2 61.70(13) . . ? O1 Nd1 N2 118.23(14) . . ? O2 Nd1 N2 80.85(13) 1_455 . ? O1W Nd1 N2 68.15(14) . . ? O6 Nd1 N2 138.04(14) 2_765 . ? O5 Nd1 N2 122.86(13) . . ? O2W Nd1 N2 67.84(14) . . ? N1 Nd1 N2 133.89(13) . . ? O1 C1 O2 125.0(5) . . ? O1 C1 C2 117.4(5) . . ? O2 C1 C2 117.7(5) . . ? N1 C2 C3 121.1(5) . 2_775 ? N1 C2 C1 115.1(5) . . ? C3 C2 C1 123.7(5) 2_775 . ? N1 C3 C2 121.7(5) . 2_775 ? N1 C3 H3 119.1 . . ? C2 C3 H3 119.1 2_775 . ? O4 C4 O3 124.7(5) . . ? O4 C4 C5 118.7(5) . . ? O3 C4 C5 116.7(5) . . ? N2 C5 C6 121.5(5) . 2_666 ? N2 C5 C4 116.3(5) . . ? C6 C5 C4 122.2(5) 2_666 . ? N2 C6 C5 121.7(5) . 2_666 ? N2 C6 H6 119.1 . . ? C5 C6 H6 119.1 2_666 . ? O6 C7 O5 126.5(5) . . ? O6 C7 C7 116.5(6) . 2_765 ? O5 C7 C7 117.0(6) . 2_765 ? C3 N1 C2 117.1(5) . . ? C3 N1 Nd1 126.7(4) . . ? C2 N1 Nd1 115.2(3) . . ? C6 N2 C5 116.7(5) . . ? C6 N2 Nd1 128.9(3) . . ? C5 N2 Nd1 114.3(4) . . ? C1 O1 Nd1 128.0(3) . . ? C1 O2 Nd1 131.9(3) . 1_655 ? C4 O3 Nd1 130.9(4) . . ? C7 O5 Nd1 120.3(3) . . ? C7 O6 Nd1 120.6(3) . 2_765 ? Nd1 O1W H1W 118.5 . . ? Nd1 O1W H2W 130.3 . . ? H1W O1W H2W 103.3 . . ? Nd1 O2W H3W 105.8 . . ? Nd1 O2W H4W 130.3 . . ? H3W O2W H4W 101.5 . . ? H5W O3W H6W 98.1 . . ? H8W O4W H7W 97.9 . . ? H9W O5W H10W 98.3 . . ? H12W O6W H11W 97.4 . . ? H14W O7W H13W 103.5 . . ? 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 O1 C1 C2 N1 -3.6(7) . . . . ? O2 C1 C2 N1 174.5(4) . . . . ? O1 C1 C2 C3 179.7(5) . . . 2_775 ? O2 C1 C2 C3 -2.1(8) . . . 2_775 ? O4 C4 C5 N2 178.5(6) . . . . ? O3 C4 C5 N2 -1.1(8) . . . . ? O4 C4 C5 C6 -2.4(9) . . . 2_666 ? O3 C4 C5 C6 178.0(6) . . . 2_666 ? C2 C3 N1 C2 -1.2(8) 2_775 . . . ? C2 C3 N1 Nd1 167.1(4) 2_775 . . . ? C3 C2 N1 C3 1.2(8) 2_775 . . . ? C1 C2 N1 C3 -175.5(4) . . . . ? C3 C2 N1 Nd1 -168.4(4) 2_775 . . . ? C1 C2 N1 Nd1 14.8(5) . . . . ? O3 Nd1 N1 C3 -169.3(4) . . . . ? O1 Nd1 N1 C3 177.2(5) . . . . ? O2 Nd1 N1 C3 -21.1(4) 1_455 . . . ? O1W Nd1 N1 C3 -102.4(4) . . . . ? O6 Nd1 N1 C3 57.7(4) 2_765 . . . ? O5 Nd1 N1 C3 114.8(4) . . . . ? O2W Nd1 N1 C3 30.9(5) . . . . ? N2 Nd1 N1 C3 -80.0(5) . . . . ? O3 Nd1 N1 C2 -0.8(4) . . . . ? O1 Nd1 N1 C2 -14.4(3) . . . . ? O2 Nd1 N1 C2 147.4(4) 1_455 . . . ? O1W Nd1 N1 C2 66.0(4) . . . . ? O6 Nd1 N1 C2 -133.8(4) 2_765 . . . ? O5 Nd1 N1 C2 -76.7(4) . . . . ? O2W Nd1 N1 C2 -160.6(3) . . . . ? N2 Nd1 N1 C2 88.5(4) . . . . ? C5 C6 N2 C5 -1.6(9) 2_666 . . . ? C5 C6 N2 Nd1 -179.1(4) 2_666 . . . ? C6 C5 N2 C6 1.6(9) 2_666 . . . ? C4 C5 N2 C6 -179.3(5) . . . . ? C6 C5 N2 Nd1 179.4(4) 2_666 . . . ? C4 C5 N2 Nd1 -1.5(6) . . . . ? O3 Nd1 N2 C6 179.7(5) . . . . ? O1 Nd1 N2 C6 133.0(5) . . . . ? O2 Nd1 N2 C6 0.5(5) 1_455 . . . ? O1W Nd1 N2 C6 79.3(5) . . . . ? O6 Nd1 N2 C6 -52.9(6) 2_765 . . . ? O5 Nd1 N2 C6 -140.6(5) . . . . ? O2W Nd1 N2 C6 -83.8(5) . . . . ? N1 Nd1 N2 C6 56.7(6) . . . . ? O3 Nd1 N2 C5 2.2(4) . . . . ? O1 Nd1 N2 C5 -44.6(4) . . . . ? O2 Nd1 N2 C5 -177.0(4) 1_455 . . . ? O1W Nd1 N2 C5 -98.2(4) . . . . ? O6 Nd1 N2 C5 129.6(4) 2_765 . . . ? O5 Nd1 N2 C5 41.9(4) . . . . ? O2W Nd1 N2 C5 98.6(4) . . . . ? N1 Nd1 N2 C5 -120.8(4) . . . . ? O2 C1 O1 Nd1 169.4(4) . . . . ? C2 C1 O1 Nd1 -12.6(7) . . . . ? O3 Nd1 O1 C1 -155.0(5) . . . . ? O2 Nd1 O1 C1 -9.1(5) 1_455 . . . ? O1W Nd1 O1 C1 -60.8(5) . . . . ? O6 Nd1 O1 C1 71.4(5) 2_765 . . . ? O5 Nd1 O1 C1 129.0(5) . . . . ? O2W Nd1 O1 C1 155.5(4) . . . . ? N1 Nd1 O1 C1 14.5(4) . . . . ? N2 Nd1 O1 C1 -112.6(5) . . . . ? O1 C1 O2 Nd1 23.4(8) . . . 1_655 ? C2 C1 O2 Nd1 -154.5(3) . . . 1_655 ? O4 C4 O3 Nd1 -175.5(5) . . . . ? C5 C4 O3 Nd1 4.1(8) . . . . ? O1 Nd1 O3 C4 134.0(5) . . . . ? O2 Nd1 O3 C4 -2.3(7) 1_455 . . . ? O1W Nd1 O3 C4 62.4(5) . . . . ? O6 Nd1 O3 C4 -134.5(5) 2_765 . . . ? O5 Nd1 O3 C4 -149.2(6) . . . . ? O2W Nd1 O3 C4 -71.0(5) . . . . ? N1 Nd1 O3 C4 121.6(5) . . . . ? N2 Nd1 O3 C4 -3.5(5) . . . . ? O6 C7 O5 Nd1 172.9(5) . . . . ? C7 C7 O5 Nd1 -6.5(9) 2_765 . . . ? O3 Nd1 O5 C7 175.7(5) . . . . ? O1 Nd1 O5 C7 -107.8(5) . . . . ? O2 Nd1 O5 C7 24.9(5) 1_455 . . . ? O1W Nd1 O5 C7 -123.5(4) . . . . ? O6 Nd1 O5 C7 7.1(4) 2_765 . . . ? O2W Nd1 O5 C7 86.9(5) . . . . ? N1 Nd1 O5 C7 -53.2(5) . . . . ? N2 Nd1 O5 C7 139.5(4) . . . . ? O5 C7 O6 Nd1 173.3(5) . . . 2_765 ? C7 C7 O6 Nd1 -7.3(8) 2_765 . . 2_765 ? _diffrn_measured_fraction_theta_max 0.968 _diffrn_reflns_theta_full 25.20 _diffrn_measured_fraction_theta_full 0.968 _refine_diff_density_max 1.178 _refine_diff_density_min -1.648 _refine_diff_density_rms 0.146 # Attachment '- 1-Sm.cif' data_1-Sm _database_code_depnum_ccdc_archive 'CCDC 742764' #TrackingRef '- 1-Sm.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety '2(C7 H6 N2 O8 Sm), 10(H O0.50)' _chemical_formula_sum 'C14 H30 N4 O25 Sm2' _chemical_formula_weight 955.12 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' Sm Sm -0.1638 3.4418 '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' _symmetry_space_group_name_Hall '-P 1' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 6.1139(12) _cell_length_b 9.9830(19) _cell_length_c 13.413(3) _cell_angle_alpha 68.931(2) _cell_angle_beta 80.960(2) _cell_angle_gamma 76.689(2) _cell_volume 740.9(3) _cell_formula_units_Z 1 _cell_measurement_temperature 298(2) _cell_measurement_reflns_used 1601 _cell_measurement_theta_min 2.28 _cell_measurement_theta_max 25.35 _exptl_crystal_description block _exptl_crystal_colour colorless _exptl_crystal_size_max 0.23 _exptl_crystal_size_mid 0.16 _exptl_crystal_size_min 0.11 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 2.141 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 466 _exptl_absorpt_coefficient_mu 4.032 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.4574 _exptl_absorpt_correction_T_max 0.6654 _exptl_absorpt_process_details 'SADABS, Bruker(2002)' _exptl_special_details ; ? ; _diffrn_ambient_temperature 298(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type ? _diffrn_measurement_method ? _diffrn_detector_area_resol_mean ? _diffrn_reflns_number 3789 _diffrn_reflns_av_R_equivalents 0.0223 _diffrn_reflns_av_sigmaI/netI 0.0519 _diffrn_reflns_limit_h_min -6 _diffrn_reflns_limit_h_max 7 _diffrn_reflns_limit_k_min -11 _diffrn_reflns_limit_k_max 11 _diffrn_reflns_limit_l_min -9 _diffrn_reflns_limit_l_max 16 _diffrn_reflns_theta_min 1.63 _diffrn_reflns_theta_max 25.20 _reflns_number_total 2625 _reflns_number_gt 2286 _reflns_threshold_expression >2sigma(I) _computing_data_collection ? _computing_cell_refinement ? _computing_data_reduction ? _computing_structure_solution 'SHELXS-97 (Sheldrick, 2008)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _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^)+(0.0471P)^2^+1.6567P] 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 2625 _refine_ls_number_parameters 208 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0464 _refine_ls_R_factor_gt 0.0374 _refine_ls_wR_factor_ref 0.0867 _refine_ls_wR_factor_gt 0.0839 _refine_ls_goodness_of_fit_ref 0.987 _refine_ls_restrained_S_all 0.987 _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 Sm1 Sm 0.83082(6) 0.61458(4) 0.19641(3) 0.01940(13) Uani 1 1 d . . . C1 C 1.2863(11) 0.7672(7) 0.1404(5) 0.0231(14) Uani 1 1 d . . . C2 C 1.1325(10) 0.8953(7) 0.0684(5) 0.0208(14) Uani 1 1 d . . . C3 C 0.8102(10) 0.9686(7) -0.0151(5) 0.0197(14) Uani 1 1 d . . . H3 H 0.6775 0.9504 -0.0290 0.024 Uiso 1 1 calc R . . C4 C 0.9484(12) 0.3835(8) 0.4395(5) 0.0274(15) Uani 1 1 d . . . C5 C 0.7116(11) 0.4439(7) 0.4728(5) 0.0232(14) Uani 1 1 d . . . C6 C 0.3838(12) 0.6022(8) 0.4218(5) 0.0284(16) Uani 1 1 d . . . H6 H 0.2980 0.6742 0.3694 0.034 Uiso 1 1 calc R . . C7 C 1.0892(11) 0.4407(7) 0.0333(5) 0.0262(15) Uani 1 1 d . . . N1 N 0.9389(8) 0.8647(6) 0.0546(4) 0.0212(12) Uani 1 1 d . . . N2 N 0.5938(9) 0.5462(6) 0.3941(4) 0.0259(13) Uani 1 1 d . . . O1 O 1.2129(8) 0.6517(5) 0.1843(4) 0.0317(12) Uani 1 1 d . . . O2 O 1.4775(7) 0.7850(5) 0.1509(4) 0.0251(10) Uani 1 1 d . . . O3 O 1.0143(8) 0.4311(5) 0.3423(4) 0.0343(12) Uani 1 1 d . . . O4 O 1.0668(9) 0.2907(6) 0.5099(4) 0.0443(14) Uani 1 1 d . . . O5 O 1.0835(8) 0.4305(5) 0.1296(4) 0.0342(12) Uani 1 1 d . . . O6 O 1.2237(8) 0.3624(5) -0.0133(4) 0.0288(11) Uani 1 1 d . . . O1W O 0.8259(9) 0.7913(5) 0.2842(4) 0.0376(13) Uani 1 1 d . . . H2W H 0.8669 0.7814 0.3451 0.056 Uiso 1 1 d R . . H1W H 0.7082 0.8582 0.2815 0.056 Uiso 1 1 d R . . O2W O 0.5911(8) 0.4355(5) 0.2195(4) 0.0324(12) Uani 1 1 d . . . H3W H 0.4593 0.4844 0.2116 0.049 Uiso 1 1 d R . . H4W H 0.5690 0.3623 0.2712 0.049 Uiso 1 1 d R . . O3W O 0.6350(13) 0.2813(10) 0.0843(7) 0.097(3) Uani 1 1 d . . . H5W H 0.6223 0.2007 0.1359 0.145 Uiso 1 1 d R . . H6W H 0.6872 0.2453 0.0339 0.145 Uiso 1 1 d R . . O4W O 0.5068(15) 0.2056(10) 0.4133(7) 0.105(3) Uani 1 1 d . . . H8W H 0.4581 0.1320 0.4618 0.158 Uiso 1 1 d R . . H7W H 0.6348 0.1590 0.3950 0.158 Uiso 1 1 d R . . O5W O 0.532(3) 0.0399(12) 0.2651(12) 0.215(8) Uani 1 1 d . . . H9W H 0.4761 -0.0164 0.3240 0.323 Uiso 1 1 d R . . H10W H 0.4110 0.1030 0.2455 0.323 Uiso 1 1 d R . . O6W O 0.069(3) 0.1202(13) 0.2678(13) 0.221(8) Uani 1 1 d . . . H12W H -0.0508 0.1290 0.2380 0.332 Uiso 1 1 d R . . H11W H 0.0722 0.2118 0.2486 0.332 Uiso 1 1 d R . . O7W O 0.090(4) 0.981(3) 0.513(3) 0.173(12) Uani 0.50 1 d P . . H14W H 0.1036 0.9760 0.5776 0.260 Uiso 0.50 1 d PR . . H13W H 0.2137 1.0108 0.4833 0.260 Uiso 0.50 1 d PR . . 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 Sm1 0.01626(19) 0.0245(2) 0.01498(18) -0.00438(13) 0.00106(12) -0.00428(13) C1 0.021(3) 0.027(4) 0.017(3) -0.006(3) -0.005(3) 0.003(3) C2 0.017(3) 0.029(4) 0.014(3) -0.006(3) -0.002(3) -0.001(3) C3 0.015(3) 0.020(3) 0.022(3) -0.004(3) 0.003(3) -0.008(3) C4 0.033(4) 0.030(4) 0.016(3) -0.003(3) -0.005(3) -0.005(3) C5 0.027(4) 0.026(4) 0.019(3) -0.007(3) -0.002(3) -0.008(3) C6 0.029(4) 0.034(4) 0.016(3) -0.002(3) -0.001(3) -0.004(3) C7 0.023(4) 0.032(4) 0.021(4) -0.006(3) 0.002(3) -0.008(3) N1 0.015(3) 0.028(3) 0.018(3) -0.006(2) 0.002(2) -0.005(2) N2 0.027(3) 0.028(3) 0.018(3) -0.002(2) 0.000(2) -0.009(3) O1 0.019(2) 0.028(3) 0.034(3) 0.008(2) -0.005(2) -0.004(2) O2 0.019(2) 0.031(3) 0.024(3) -0.005(2) -0.0042(19) -0.007(2) O3 0.032(3) 0.044(3) 0.012(2) 0.002(2) 0.002(2) -0.001(2) O4 0.041(3) 0.057(4) 0.018(3) -0.001(2) -0.004(2) 0.006(3) O5 0.036(3) 0.038(3) 0.024(3) -0.013(2) -0.005(2) 0.007(2) O6 0.029(3) 0.033(3) 0.024(3) -0.016(2) -0.002(2) 0.005(2) O1W 0.051(3) 0.039(3) 0.026(3) -0.011(2) -0.009(2) -0.009(3) O2W 0.023(3) 0.032(3) 0.040(3) -0.007(2) 0.002(2) -0.010(2) O3W 0.067(5) 0.148(8) 0.105(7) -0.093(6) -0.010(5) 0.007(5) O4W 0.088(6) 0.112(7) 0.103(7) -0.033(6) -0.003(5) -0.004(6) O5W 0.33(2) 0.096(8) 0.243(16) -0.101(10) -0.165(15) 0.089(11) O6W 0.255(19) 0.108(10) 0.221(17) 0.004(10) -0.026(14) 0.026(11) O7W 0.14(3) 0.110(17) 0.28(3) -0.035(19) -0.10(2) -0.021(18) _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 Sm1 O3 2.368(4) . ? Sm1 O2 2.431(4) 1_455 ? Sm1 O1 2.420(4) . ? Sm1 O1W 2.441(5) . ? Sm1 O5 2.451(5) . ? Sm1 O6 2.453(4) 2_765 ? Sm1 O2W 2.471(5) . ? Sm1 N1 2.691(5) . ? Sm1 N2 2.746(5) . ? C1 O1 1.243(8) . ? C1 O2 1.258(8) . ? C1 C2 1.515(9) . ? C2 N1 1.344(8) . ? C2 C3 1.387(9) 2_775 ? C3 N1 1.314(8) . ? C3 H3 0.9300 . ? C4 O4 1.245(8) . ? C4 O3 1.251(8) . ? C4 C5 1.500(10) . ? C5 N2 1.342(8) . ? C5 C6 1.396(9) 2_666 ? C6 N2 1.329(9) . ? C6 C5 1.396(9) 2_666 ? C6 H6 0.9300 . ? C7 O5 1.254(8) . ? C7 O6 1.254(8) . ? C7 C7 1.530(13) 2_765 ? O2 Sm1 2.431(4) 1_655 ? O1W H2W 0.8565 . ? O1W H1W 0.8574 . ? O2W H3W 0.8413 . ? O2W H4W 0.8268 . ? O3W H5W 0.8617 . ? O3W H6W 0.8614 . ? O4W H8W 0.8651 . ? O4W H7W 0.8621 . ? O5W H9W 0.8619 . ? O5W H10W 0.8614 . ? O6W H12W 0.8603 . ? O6W H11W 0.8604 . ? O7W H14W 0.8621 . ? O7W H13W 0.8616 . ? 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 Sm1 O2 142.34(16) . 1_455 ? O3 Sm1 O1 71.78(16) . . ? O2 Sm1 O1 131.99(15) 1_455 . ? O3 Sm1 O1W 88.30(18) . . ? O2 Sm1 O1W 76.42(16) 1_455 . ? O1 Sm1 O1W 71.99(18) . . ? O3 Sm1 O5 71.57(17) . . ? O2 Sm1 O5 137.40(16) 1_455 . ? O1 Sm1 O5 71.96(18) . . ? O1W Sm1 O5 142.69(18) . . ? O3 Sm1 O6 135.70(17) . 2_765 ? O2 Sm1 O6 73.64(15) 1_455 2_765 ? O1 Sm1 O6 103.98(16) . 2_765 ? O1W Sm1 O6 133.58(16) . 2_765 ? O5 Sm1 O6 65.57(15) . 2_765 ? O3 Sm1 O2W 84.75(17) . . ? O2 Sm1 O2W 81.68(15) 1_455 . ? O1 Sm1 O2W 145.48(17) . . ? O1W Sm1 O2W 133.61(17) . . ? O5 Sm1 O2W 76.84(17) . . ? O6 Sm1 O2W 75.37(16) 2_765 . ? O3 Sm1 N1 132.58(16) . . ? O2 Sm1 N1 73.39(15) 1_455 . ? O1 Sm1 N1 61.94(15) . . ? O1W Sm1 N1 68.78(16) . . ? O5 Sm1 N1 101.87(16) . . ? O6 Sm1 N1 69.12(16) 2_765 . ? O2W Sm1 N1 140.98(15) . . ? O3 Sm1 N2 62.12(16) . . ? O2 Sm1 N2 80.23(16) 1_455 . ? O1 Sm1 N2 118.35(16) . . ? O1W Sm1 N2 68.20(17) . . ? O5 Sm1 N2 123.08(16) . . ? O6 Sm1 N2 137.53(16) 2_765 . ? O2W Sm1 N2 68.09(16) . . ? N1 Sm1 N2 133.51(16) . . ? O1 C1 O2 125.0(6) . . ? O1 C1 C2 116.9(6) . . ? O2 C1 C2 118.1(6) . . ? N1 C2 C3 121.8(6) . 2_775 ? N1 C2 C1 114.6(6) . . ? C3 C2 C1 123.5(6) 2_775 . ? N1 C3 C2 121.5(6) . 2_775 ? N1 C3 H3 119.2 . . ? C2 C3 H3 119.2 2_775 . ? O4 C4 O3 124.4(7) . . ? O4 C4 C5 118.2(6) . . ? O3 C4 C5 117.4(6) . . ? N2 C5 C6 121.3(6) . 2_666 ? N2 C5 C4 115.7(6) . . ? C6 C5 C4 123.0(6) 2_666 . ? N2 C6 C5 121.9(6) . 2_666 ? N2 C6 H6 119.0 . . ? C5 C6 H6 119.0 2_666 . ? O5 C7 O6 126.7(6) . . ? O5 C7 C7 116.5(8) . 2_765 ? O6 C7 C7 116.8(7) . 2_765 ? C3 N1 C2 116.6(5) . . ? C3 N1 Sm1 127.3(4) . . ? C2 N1 Sm1 115.3(4) . . ? C6 N2 C5 116.8(6) . . ? C6 N2 Sm1 129.1(4) . . ? C5 N2 Sm1 114.1(4) . . ? C1 O1 Sm1 128.1(4) . . ? C1 O2 Sm1 132.2(4) . 1_655 ? C4 O3 Sm1 130.6(4) . . ? C7 O5 Sm1 120.2(4) . . ? C7 O6 Sm1 120.0(4) . 2_765 ? Sm1 O1W H2W 132.1 . . ? Sm1 O1W H1W 118.2 . . ? H2W O1W H1W 99.2 . . ? Sm1 O2W H3W 105.4 . . ? Sm1 O2W H4W 130.5 . . ? H3W O2W H4W 101.4 . . ? H5W O3W H6W 98.3 . . ? H8W O4W H7W 98.0 . . ? H9W O5W H10W 98.2 . . ? H12W O6W H11W 97.4 . . ? H14W O7W H13W 98.2 . . ? _diffrn_measured_fraction_theta_max 0.984 _diffrn_reflns_theta_full 25.20 _diffrn_measured_fraction_theta_full 0.984 _refine_diff_density_max 1.450 _refine_diff_density_min -0.896 _refine_diff_density_rms 0.165 # Attachment '- 1-Eu.cif' data_1-Eu _database_code_depnum_ccdc_archive 'CCDC 742765' #TrackingRef '- 1-Eu.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety '2(C7 H6 Eu N2 O8), 10(H O0.50)' _chemical_formula_sum 'C14 H30 Eu2 N4 O25' _chemical_formula_weight 958.34 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' _symmetry_space_group_name_Hall '-P 1' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 6.1009(8) _cell_length_b 9.9758(16) _cell_length_c 13.3825(18) _cell_angle_alpha 68.8710(10) _cell_angle_beta 81.033(2) _cell_angle_gamma 76.750(2) _cell_volume 737.09(18) _cell_formula_units_Z 1 _cell_measurement_temperature 298(2) _cell_measurement_reflns_used 1610 _cell_measurement_theta_min 3.18 _cell_measurement_theta_max 24.52 _exptl_crystal_description block _exptl_crystal_colour colorless _exptl_crystal_size_max 0.16 _exptl_crystal_size_mid 0.12 _exptl_crystal_size_min 0.06 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 2.159 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 468 _exptl_absorpt_coefficient_mu 4.324 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.5446 _exptl_absorpt_correction_T_max 0.7814 _exptl_absorpt_process_details 'SADABS, Bruker(2002)' _exptl_special_details ; ? ; _diffrn_ambient_temperature 298(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type ? _diffrn_measurement_method ? _diffrn_detector_area_resol_mean ? _diffrn_reflns_number 3845 _diffrn_reflns_av_R_equivalents 0.0242 _diffrn_reflns_av_sigmaI/netI 0.0482 _diffrn_reflns_limit_h_min -7 _diffrn_reflns_limit_h_max 7 _diffrn_reflns_limit_k_min -11 _diffrn_reflns_limit_k_max 8 _diffrn_reflns_limit_l_min -16 _diffrn_reflns_limit_l_max 15 _diffrn_reflns_theta_min 1.64 _diffrn_reflns_theta_max 25.20 _reflns_number_total 2613 _reflns_number_gt 2320 _reflns_threshold_expression >2sigma(I) _computing_data_collection ? _computing_cell_refinement ? _computing_data_reduction ? _computing_structure_solution 'SHELXS-97 (Sheldrick, 2008)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _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^)+(0.0362P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 2613 _refine_ls_number_parameters 208 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0376 _refine_ls_R_factor_gt 0.0320 _refine_ls_wR_factor_ref 0.0742 _refine_ls_wR_factor_gt 0.0720 _refine_ls_goodness_of_fit_ref 1.081 _refine_ls_restrained_S_all 1.081 _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 0.83164(5) 0.61437(3) 0.19600(2) 0.01724(11) Uani 1 1 d . . . C1 C 1.2866(9) 0.7678(6) 0.1416(4) 0.0187(12) Uani 1 1 d . . . C2 C 1.1325(9) 0.8950(6) 0.0681(4) 0.0184(12) Uani 1 1 d . . . C3 C 0.8095(9) 0.9706(6) -0.0154(4) 0.0188(12) Uani 1 1 d . . . H3 H 0.6752 0.9536 -0.0288 0.023 Uiso 1 1 calc R . . C4 C 0.9507(10) 0.3836(6) 0.4398(5) 0.0247(13) Uani 1 1 d . . . C5 C 0.7097(10) 0.4438(6) 0.4730(4) 0.0230(13) Uani 1 1 d . . . C6 C 0.3816(10) 0.6025(6) 0.4230(4) 0.0238(13) Uani 1 1 d . . . H6 H 0.2940 0.6747 0.3711 0.029 Uiso 1 1 calc R . . C7 C 1.0876(10) 0.4393(6) 0.0345(5) 0.0240(13) Uani 1 1 d . . . N1 N 0.9395(7) 0.8644(5) 0.0542(3) 0.0183(10) Uani 1 1 d . . . N2 N 0.5939(8) 0.5470(5) 0.3936(4) 0.0248(11) Uani 1 1 d . . . O1 O 1.2144(7) 0.6502(4) 0.1843(3) 0.0291(10) Uani 1 1 d . . . O2 O 1.4785(6) 0.7843(4) 0.1509(3) 0.0215(9) Uani 1 1 d . . . O3 O 1.0142(7) 0.4303(5) 0.3426(3) 0.0317(10) Uani 1 1 d . . . O4 O 1.0682(8) 0.2904(5) 0.5102(3) 0.0439(13) Uani 1 1 d . . . O5 O 1.0844(7) 0.4293(4) 0.1301(3) 0.0295(10) Uani 1 1 d . . . O6 O 1.2235(7) 0.3625(4) -0.0133(3) 0.0265(9) Uani 1 1 d . . . O1W O 0.8264(8) 0.7904(5) 0.2838(3) 0.0343(11) Uani 1 1 d . . . H2W H 0.8674 0.7806 0.3446 0.051 Uiso 1 1 d R . . H1W H 0.7087 0.8574 0.2811 0.051 Uiso 1 1 d R . . O2W O 0.5919(7) 0.4368(4) 0.2192(3) 0.0311(10) Uani 1 1 d . . . H3W H 0.4601 0.4857 0.2112 0.047 Uiso 1 1 d R . . H4W H 0.5698 0.3636 0.2708 0.047 Uiso 1 1 d R . . O3W O 0.6365(10) 0.2808(8) 0.0845(5) 0.090(2) Uani 1 1 d . . . H5W H 0.6239 0.2003 0.1360 0.134 Uiso 1 1 d R . . H6W H 0.6887 0.2448 0.0340 0.134 Uiso 1 1 d R . . O4W O 0.5091(13) 0.2019(9) 0.4138(6) 0.103(3) Uani 1 1 d . . . H8W H 0.4604 0.1282 0.4624 0.155 Uiso 1 1 d R . . H7W H 0.6371 0.1552 0.3955 0.155 Uiso 1 1 d R . . O5W O 0.535(2) 0.0393(9) 0.2638(9) 0.202(7) Uani 1 1 d . . . H9W H 0.4792 -0.0170 0.3228 0.304 Uiso 1 1 d R . . H10W H 0.4142 0.1023 0.2443 0.304 Uiso 1 1 d R . . O6W O 0.070(2) 0.1190(10) 0.2687(9) 0.195(5) Uani 1 1 d . . . H12W H -0.0494 0.1278 0.2390 0.292 Uiso 1 1 d R . . H11W H 0.0736 0.2106 0.2495 0.292 Uiso 1 1 d R . . O7W O 0.086(4) 0.979(3) 0.510(3) 0.186(11) Uani 0.50 1 d P . . H14W H 0.0994 0.9740 0.5747 0.279 Uiso 0.50 1 d PR . . H13W H 0.2095 1.0087 0.4805 0.279 Uiso 0.50 1 d PR . . 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 0.01407(16) 0.02027(17) 0.01559(16) -0.00381(11) -0.00298(10) -0.00224(11) C1 0.013(3) 0.021(3) 0.017(3) -0.004(2) 0.000(2) 0.001(2) C2 0.014(3) 0.023(3) 0.016(3) -0.003(2) -0.004(2) -0.003(2) C3 0.010(3) 0.028(3) 0.016(3) -0.006(2) -0.004(2) -0.001(2) C4 0.026(3) 0.025(3) 0.023(3) -0.009(3) -0.005(3) -0.003(3) C5 0.026(3) 0.024(3) 0.019(3) -0.007(2) -0.002(2) -0.004(3) C6 0.027(3) 0.023(3) 0.019(3) -0.001(2) -0.008(2) -0.006(3) C7 0.026(3) 0.025(3) 0.022(3) -0.007(3) -0.005(3) -0.008(3) N1 0.014(2) 0.022(3) 0.017(2) -0.004(2) -0.0004(18) -0.0037(19) N2 0.032(3) 0.024(3) 0.018(3) -0.004(2) -0.003(2) -0.009(2) O1 0.015(2) 0.020(2) 0.043(3) 0.0029(19) -0.0055(18) -0.0054(17) O2 0.012(2) 0.022(2) 0.029(2) -0.0058(17) -0.0061(16) -0.0028(16) O3 0.026(2) 0.041(3) 0.017(2) -0.0011(19) -0.0009(18) 0.000(2) O4 0.036(3) 0.056(3) 0.021(2) -0.001(2) -0.008(2) 0.014(2) O5 0.032(2) 0.034(2) 0.021(2) -0.0111(19) -0.0079(18) 0.0049(19) O6 0.026(2) 0.031(2) 0.023(2) -0.0133(19) -0.0055(18) 0.0040(18) O1W 0.046(3) 0.036(3) 0.024(2) -0.012(2) -0.005(2) -0.009(2) O2W 0.023(2) 0.026(2) 0.043(3) -0.009(2) -0.0023(19) -0.0072(18) O3W 0.061(4) 0.135(6) 0.091(5) -0.075(5) -0.009(4) 0.011(4) O4W 0.089(6) 0.118(6) 0.084(5) -0.029(5) 0.012(4) -0.002(5) O5W 0.317(17) 0.086(7) 0.225(13) -0.092(8) -0.157(12) 0.077(8) O6W 0.226(14) 0.109(8) 0.179(12) 0.007(7) -0.019(10) 0.014(8) O7W 0.17(3) 0.108(16) 0.26(3) -0.031(17) -0.12(2) 0.025(17) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag Eu1 O3 2.368(4) . ? Eu1 O1 2.415(4) . ? Eu1 O2 2.423(4) 1_455 ? Eu1 O1W 2.432(4) . ? Eu1 O6 2.441(4) 2_765 ? Eu1 O5 2.451(4) . ? Eu1 O2W 2.454(4) . ? Eu1 N1 2.684(4) . ? Eu1 N2 2.742(5) . ? C1 O2 1.249(7) . ? C1 O1 1.254(7) . ? C1 C2 1.517(7) . ? C2 N1 1.337(7) . ? C2 C3 1.370(8) 2_775 ? C3 N1 1.324(7) . ? C3 H3 0.9300 . ? C4 O4 1.240(7) . ? C4 O3 1.244(7) . ? C4 C5 1.518(8) . ? C5 N2 1.342(7) . ? C5 C6 1.368(8) 2_666 ? C6 N2 1.345(7) . ? C6 C5 1.368(8) 2_666 ? C6 H6 0.9300 . ? C7 O5 1.245(7) . ? C7 O6 1.257(7) . ? C7 C7 1.539(11) 2_765 ? O1W H2W 0.8542 . ? O1W H1W 0.8567 . ? O2W H3W 0.8400 . ? O2W H4W 0.8250 . ? O3W H5W 0.8600 . ? O3W H6W 0.8605 . ? O4W H8W 0.8633 . ? O4W H7W 0.8614 . ? O5W H9W 0.8600 . ? O5W H10W 0.8600 . ? O6W H12W 0.8580 . ? O6W H11W 0.8595 . ? O7W H14W 0.8600 . ? O7W H13W 0.8600 . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag O3 Eu1 O1 71.77(14) . . ? O3 Eu1 O2 141.99(13) . 1_455 ? O1 Eu1 O2 132.33(13) . 1_455 ? O3 Eu1 O1W 88.36(15) . . ? O1 Eu1 O1W 72.29(15) . . ? O2 Eu1 O1W 76.26(14) 1_455 . ? O3 Eu1 O6 135.75(13) . 2_765 ? O1 Eu1 O6 104.08(14) . 2_765 ? O2 Eu1 O6 73.75(13) 1_455 2_765 ? O1W Eu1 O6 133.59(14) . 2_765 ? O3 Eu1 O5 71.38(13) . . ? O1 Eu1 O5 71.79(14) . . ? O2 Eu1 O5 137.71(13) 1_455 . ? O1W Eu1 O5 142.76(15) . . ? O6 Eu1 O5 65.85(12) 2_765 . ? O3 Eu1 O2W 84.62(15) . . ? O1 Eu1 O2W 145.34(14) . . ? O2 Eu1 O2W 81.53(13) 1_455 . ? O1W Eu1 O2W 133.37(14) . . ? O6 Eu1 O2W 75.37(14) 2_765 . ? O5 Eu1 O2W 76.87(14) . . ? O3 Eu1 N1 132.79(14) . . ? O1 Eu1 N1 62.21(13) . . ? O2 Eu1 N1 73.47(13) 1_455 . ? O1W Eu1 N1 68.79(14) . . ? O6 Eu1 N1 69.20(13) 2_765 . ? O5 Eu1 N1 102.19(14) . . ? O2W Eu1 N1 140.98(13) . . ? O3 Eu1 N2 62.13(14) . . ? O1 Eu1 N2 118.34(14) . . ? O2 Eu1 N2 79.87(14) 1_455 . ? O1W Eu1 N2 67.95(14) . . ? O6 Eu1 N2 137.45(14) 2_765 . ? O5 Eu1 N2 123.03(14) . . ? O2W Eu1 N2 68.10(14) . . ? N1 Eu1 N2 133.23(13) . . ? O2 C1 O1 124.7(5) . . ? O2 C1 C2 118.7(5) . . ? O1 C1 C2 116.5(5) . . ? N1 C2 C3 122.1(5) . 2_775 ? N1 C2 C1 115.0(5) . . ? C3 C2 C1 122.8(5) 2_775 . ? N1 C3 C2 121.8(5) . 2_775 ? N1 C3 H3 119.1 . . ? C2 C3 H3 119.1 2_775 . ? O4 C4 O3 124.8(6) . . ? O4 C4 C5 118.3(5) . . ? O3 C4 C5 116.9(5) . . ? N2 C5 C6 122.5(5) . 2_666 ? N2 C5 C4 115.3(5) . . ? C6 C5 C4 122.2(5) 2_666 . ? N2 C6 C5 122.1(5) . 2_666 ? N2 C6 H6 119.0 . . ? C5 C6 H6 119.0 2_666 . ? O5 C7 O6 126.8(5) . . ? O5 C7 C7 117.4(6) . 2_765 ? O6 C7 C7 115.8(6) . 2_765 ? C3 N1 C2 116.1(5) . . ? C3 N1 Eu1 127.7(4) . . ? C2 N1 Eu1 115.3(3) . . ? C5 N2 C6 115.5(5) . . ? C5 N2 Eu1 114.5(4) . . ? C6 N2 Eu1 130.1(4) . . ? C1 O1 Eu1 127.5(3) . . ? C1 O2 Eu1 132.8(4) . 1_655 ? C4 O3 Eu1 131.1(4) . . ? C7 O5 Eu1 119.7(4) . . ? C7 O6 Eu1 120.4(3) . 2_765 ? Eu1 O1W H2W 132.1 . . ? Eu1 O1W H1W 118.3 . . ? H2W O1W H1W 99.1 . . ? Eu1 O2W H3W 105.5 . . ? Eu1 O2W H4W 130.6 . . ? H3W O2W H4W 101.4 . . ? H5W O3W H6W 98.2 . . ? H8W O4W H7W 98.0 . . ? H9W O5W H10W 98.2 . . ? H12W O6W H11W 97.5 . . ? H14W O7W H13W 98.2 . . ? _diffrn_measured_fraction_theta_max 0.985 _diffrn_reflns_theta_full 25.20 _diffrn_measured_fraction_theta_full 0.985 _refine_diff_density_max 0.848 _refine_diff_density_min -0.738 _refine_diff_density_rms 0.148 # Attachment '- 1-Gd.cif' data_1-gd _database_code_depnum_ccdc_archive 'CCDC 742766' #TrackingRef '- 1-Gd.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety '2(C7 H6 Gd N2 O8), 10(H O0.50)' _chemical_formula_sum 'C14 H30 Gd2 N4 O25' _chemical_formula_weight 968.92 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' Gd Gd -0.1653 3.9035 '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' _symmetry_space_group_name_Hall '-P 1' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 6.0922(5) _cell_length_b 9.9633(9) _cell_length_c 13.3598(12) _cell_angle_alpha 68.8530(10) _cell_angle_beta 81.1040(10) _cell_angle_gamma 76.8480(10) _cell_volume 734.12(11) _cell_formula_units_Z 1 _cell_measurement_temperature 298(2) _cell_measurement_reflns_used 3552 _cell_measurement_theta_min 2.23 _cell_measurement_theta_max 27.86 _exptl_crystal_description block _exptl_crystal_colour colorless _exptl_crystal_size_max 0.16 _exptl_crystal_size_mid 0.12 _exptl_crystal_size_min 0.10 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 2.192 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 470 _exptl_absorpt_coefficient_mu 4.587 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.5273 _exptl_absorpt_correction_T_max 0.6570 _exptl_absorpt_process_details 'SADABS, Bruker(2002)' _exptl_special_details ; ? ; _diffrn_ambient_temperature 298(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type ? _diffrn_measurement_method ? _diffrn_detector_area_resol_mean ? _diffrn_reflns_number 3804 _diffrn_reflns_av_R_equivalents 0.0141 _diffrn_reflns_av_sigmaI/netI 0.0251 _diffrn_reflns_limit_h_min -7 _diffrn_reflns_limit_h_max 7 _diffrn_reflns_limit_k_min -11 _diffrn_reflns_limit_k_max 8 _diffrn_reflns_limit_l_min -15 _diffrn_reflns_limit_l_max 15 _diffrn_reflns_theta_min 2.23 _diffrn_reflns_theta_max 25.20 _reflns_number_total 2597 _reflns_number_gt 2468 _reflns_threshold_expression >2sigma(I) _computing_data_collection ? _computing_cell_refinement ? _computing_data_reduction ? _computing_structure_solution 'SHELXS-97 (Sheldrick, 2008)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _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^)+(0.0290P)^2^+1.4427P] 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 2597 _refine_ls_number_parameters 208 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0221 _refine_ls_R_factor_gt 0.0209 _refine_ls_wR_factor_ref 0.0533 _refine_ls_wR_factor_gt 0.0526 _refine_ls_goodness_of_fit_ref 1.021 _refine_ls_restrained_S_all 1.021 _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 0.83214(3) 0.614290(17) 0.195715(13) 0.01533(7) Uani 1 1 d . . . C1 C 1.2883(6) 0.7661(4) 0.1410(3) 0.0176(7) Uani 1 1 d . . . C2 C 1.1340(6) 0.8934(4) 0.0687(3) 0.0168(7) Uani 1 1 d . . . C3 C 0.8079(6) 0.9702(4) -0.0152(3) 0.0192(7) Uani 1 1 d . . . H3 H 0.6731 0.9529 -0.0281 0.023 Uiso 1 1 calc R . . C4 C 0.9507(7) 0.3826(4) 0.4395(3) 0.0234(8) Uani 1 1 d . . . C5 C 0.7101(6) 0.4441(4) 0.4728(3) 0.0212(8) Uani 1 1 d . . . C6 C 0.3828(7) 0.6024(4) 0.4224(3) 0.0252(8) Uani 1 1 d . . . H6 H 0.2960 0.6752 0.3703 0.030 Uiso 1 1 calc R . . C7 C 1.0888(6) 0.4399(4) 0.0345(3) 0.0222(8) Uani 1 1 d . . . N1 N 0.9401(5) 0.8637(3) 0.0542(2) 0.0188(6) Uani 1 1 d . . . N2 N 0.5934(5) 0.5465(3) 0.3933(2) 0.0235(7) Uani 1 1 d . . . O1 O 1.2142(4) 0.6493(3) 0.1837(2) 0.0272(6) Uani 1 1 d . . . O2 O 1.4799(4) 0.7834(3) 0.1514(2) 0.0221(6) Uani 1 1 d . . . O3 O 1.0142(5) 0.4315(3) 0.3418(2) 0.0293(6) Uani 1 1 d . . . O4 O 1.0691(5) 0.2906(4) 0.5102(2) 0.0400(8) Uani 1 1 d . . . O5 O 1.0847(5) 0.4295(3) 0.1303(2) 0.0284(6) Uani 1 1 d . . . O6 O 1.2230(4) 0.3612(3) -0.0127(2) 0.0257(6) Uani 1 1 d . . . O1W O 0.8284(5) 0.7891(3) 0.2834(2) 0.0306(6) Uani 1 1 d . . . H2W H 0.8694 0.7792 0.3443 0.046 Uiso 1 1 d R . . H1W H 0.7107 0.8560 0.2807 0.046 Uiso 1 1 d R . . O2W O 0.5942(5) 0.4362(3) 0.2194(2) 0.0281(6) Uani 1 1 d . . . H3W H 0.4624 0.4852 0.2115 0.042 Uiso 1 1 d R . . H4W H 0.5721 0.3631 0.2711 0.042 Uiso 1 1 d R . . O3W O 0.6375(7) 0.2805(6) 0.0844(4) 0.0815(15) Uani 1 1 d . . . H5W H 0.6249 0.1999 0.1359 0.122 Uiso 1 1 d R . . H6W H 0.6897 0.2445 0.0340 0.122 Uiso 1 1 d R . . O4W O 0.5127(10) 0.2034(6) 0.4128(4) 0.0971(17) Uani 1 1 d . . . H8W H 0.4641 0.1298 0.4613 0.146 Uiso 1 1 d R . . H7W H 0.6407 0.1568 0.3945 0.146 Uiso 1 1 d R . . O5W O 0.5317(16) 0.0372(7) 0.2660(7) 0.172(4) Uani 1 1 d . . . H9W H 0.4755 -0.0191 0.3249 0.258 Uiso 1 1 d R . . H10W H 0.4105 0.1002 0.2464 0.258 Uiso 1 1 d R . . O6W O 0.0685(17) 0.1183(8) 0.2673(8) 0.185(4) Uani 1 1 d . . . H12W H -0.0513 0.1271 0.2376 0.278 Uiso 1 1 d R . . H11W H 0.0716 0.2099 0.2481 0.278 Uiso 1 1 d R . . O7W O 0.088(3) 0.981(2) 0.507(2) 0.164(7) Uani 0.50 1 d P . . H14W H 0.1018 0.9760 0.5716 0.247 Uiso 0.50 1 d PR . . H13W H 0.2120 1.0107 0.4774 0.247 Uiso 0.50 1 d PR . . 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 0.01302(10) 0.01829(11) 0.01259(11) -0.00244(7) -0.00166(7) -0.00303(7) C1 0.0147(17) 0.0224(18) 0.0134(17) -0.0043(14) 0.0005(14) -0.0030(14) C2 0.0141(17) 0.0210(18) 0.0130(17) -0.0033(14) 0.0006(13) -0.0039(14) C3 0.0143(17) 0.0235(18) 0.0189(19) -0.0047(15) -0.0027(14) -0.0048(14) C4 0.027(2) 0.0258(19) 0.0165(19) -0.0041(16) -0.0023(16) -0.0082(16) C5 0.024(2) 0.0231(19) 0.0164(18) -0.0052(15) -0.0013(15) -0.0070(15) C6 0.025(2) 0.029(2) 0.0162(19) -0.0026(16) -0.0050(16) -0.0007(16) C7 0.0227(19) 0.0221(19) 0.021(2) -0.0050(16) -0.0044(16) -0.0049(16) N1 0.0145(15) 0.0225(15) 0.0178(16) -0.0042(13) -0.0011(12) -0.0050(12) N2 0.0259(17) 0.0267(17) 0.0151(16) -0.0025(13) -0.0027(13) -0.0062(13) O1 0.0183(13) 0.0221(14) 0.0327(16) 0.0033(12) -0.0071(11) -0.0045(11) O2 0.0135(12) 0.0248(13) 0.0242(14) -0.0029(11) -0.0040(10) -0.0033(10) O3 0.0257(14) 0.0366(16) 0.0155(14) -0.0007(12) -0.0002(11) -0.0007(12) O4 0.0356(17) 0.051(2) 0.0178(15) -0.0018(14) -0.0062(13) 0.0084(15) O5 0.0308(15) 0.0344(16) 0.0169(14) -0.0105(12) -0.0059(11) 0.0054(12) O6 0.0255(14) 0.0304(15) 0.0204(14) -0.0110(12) -0.0050(11) 0.0025(11) O1W 0.0405(17) 0.0328(15) 0.0202(15) -0.0093(12) -0.0049(12) -0.0079(13) O2W 0.0224(14) 0.0256(14) 0.0345(16) -0.0065(12) -0.0027(12) -0.0066(11) O3W 0.056(3) 0.122(4) 0.088(4) -0.074(3) -0.013(2) 0.008(3) O4W 0.089(4) 0.103(4) 0.084(4) -0.027(3) 0.008(3) -0.006(3) O5W 0.237(10) 0.088(5) 0.203(9) -0.083(5) -0.121(8) 0.072(5) O6W 0.215(10) 0.104(6) 0.183(9) 0.005(6) -0.040(8) 0.000(6) O7W 0.132(17) 0.104(12) 0.25(2) -0.044(12) -0.043(19) -0.018(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 Gd1 O3 2.354(3) . ? Gd1 O1 2.404(3) . ? Gd1 O2 2.413(2) 1_455 ? Gd1 O1W 2.419(3) . ? Gd1 O6 2.437(3) 2_765 ? Gd1 O5 2.445(3) . ? Gd1 O2W 2.444(3) . ? Gd1 N1 2.674(3) . ? Gd1 N2 2.741(3) . ? C1 O2 1.253(4) . ? C1 O1 1.251(4) . ? C1 C2 1.510(5) . ? C2 N1 1.339(5) . ? C2 C3 1.386(5) 2_775 ? C3 N1 1.329(5) . ? C3 H3 0.9300 . ? C4 O4 1.240(5) . ? C4 O3 1.250(5) . ? C4 C5 1.519(5) . ? C5 N2 1.340(5) . ? C5 C6 1.378(5) 2_666 ? C6 N2 1.336(5) . ? C6 C5 1.378(5) 2_666 ? C6 H6 0.9300 . ? C7 O5 1.242(5) . ? C7 O6 1.260(5) . ? C7 C7 1.542(7) 2_765 ? O2 Gd1 2.413(2) 1_655 ? O1W H2W 0.8524 . ? O1W H1W 0.8564 . ? O2W H3W 0.8395 . ? O2W H4W 0.8236 . ? O3W H5W 0.8585 . ? O3W H6W 0.8598 . ? O4W H8W 0.8618 . ? O4W H7W 0.8612 . ? O5W H9W 0.8586 . ? O5W H10W 0.8594 . ? O6W H12W 0.8565 . ? O6W H11W 0.8583 . ? O7W H14W 0.8584 . ? O7W H13W 0.8587 . ? 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 Gd1 O1 71.64(9) . . ? O3 Gd1 O2 141.80(9) . 1_455 ? O1 Gd1 O2 132.55(9) . 1_455 ? O3 Gd1 O1W 88.09(10) . . ? O1 Gd1 O1W 72.43(10) . . ? O2 Gd1 O1W 76.29(9) 1_455 . ? O3 Gd1 O6 136.07(9) . 2_765 ? O1 Gd1 O6 103.78(10) . 2_765 ? O2 Gd1 O6 73.84(9) 1_455 2_765 ? O1W Gd1 O6 133.43(9) . 2_765 ? O3 Gd1 O5 71.32(9) . . ? O1 Gd1 O5 71.45(10) . . ? O2 Gd1 O5 138.02(9) 1_455 . ? O1W Gd1 O5 142.50(10) . . ? O6 Gd1 O5 66.16(8) 2_765 . ? O3 Gd1 O2W 84.47(10) . . ? O1 Gd1 O2W 144.89(9) . . ? O2 Gd1 O2W 81.77(9) 1_455 . ? O1W Gd1 O2W 133.44(10) . . ? O6 Gd1 O2W 75.83(10) 2_765 . ? O5 Gd1 O2W 76.79(10) . . ? O3 Gd1 N1 132.66(10) . . ? O1 Gd1 N1 62.28(9) . . ? O2 Gd1 N1 73.60(9) 1_455 . ? O1W Gd1 N1 68.87(9) . . ? O6 Gd1 N1 68.89(9) 2_765 . ? O5 Gd1 N1 102.21(9) . . ? O2W Gd1 N1 141.24(9) . . ? O3 Gd1 N2 62.24(9) . . ? O1 Gd1 N2 118.67(10) . . ? O2 Gd1 N2 79.57(9) 1_455 . ? O1W Gd1 N2 68.07(10) . . ? O6 Gd1 N2 137.43(9) 2_765 . ? O5 Gd1 N2 122.94(9) . . ? O2W Gd1 N2 67.86(10) . . ? N1 Gd1 N2 133.33(9) . . ? O2 C1 O1 125.3(3) . . ? O2 C1 C2 118.5(3) . . ? O1 C1 C2 116.2(3) . . ? N1 C2 C3 121.5(3) . 2_775 ? N1 C2 C1 115.3(3) . . ? C3 C2 C1 123.1(3) 2_775 . ? N1 C3 C2 121.6(3) . 2_775 ? N1 C3 H3 119.2 . . ? C2 C3 H3 119.2 2_775 . ? O4 C4 O3 125.1(4) . . ? O4 C4 C5 118.4(3) . . ? O3 C4 C5 116.5(3) . . ? N2 C5 C6 122.1(4) . 2_666 ? N2 C5 C4 115.5(3) . . ? C6 C5 C4 122.4(3) 2_666 . ? N2 C6 C5 122.2(3) . 2_666 ? N2 C6 H6 118.9 . . ? C5 C6 H6 118.9 2_666 . ? O5 C7 O6 126.7(3) . . ? O5 C7 C7 117.4(4) . 2_765 ? O6 C7 C7 115.9(4) . 2_765 ? C3 N1 C2 116.9(3) . . ? C3 N1 Gd1 127.2(2) . . ? C2 N1 Gd1 114.8(2) . . ? C5 N2 C6 115.7(3) . . ? C5 N2 Gd1 114.3(2) . . ? C6 N2 Gd1 130.0(2) . . ? C1 O1 Gd1 127.9(2) . . ? C1 O2 Gd1 132.4(2) . 1_655 ? C4 O3 Gd1 131.5(2) . . ? C7 O5 Gd1 119.6(2) . . ? C7 O6 Gd1 120.1(2) . 2_765 ? Gd1 O1W H2W 132.2 . . ? Gd1 O1W H1W 118.1 . . ? H2W O1W H1W 99.1 . . ? Gd1 O2W H3W 105.2 . . ? Gd1 O2W H4W 130.8 . . ? H3W O2W H4W 101.4 . . ? H5W O3W H6W 98.1 . . ? H8W O4W H7W 97.9 . . ? H9W O5W H10W 98.2 . . ? H12W O6W H11W 97.4 . . ? H14W O7W H13W 98.2 . . ? _diffrn_measured_fraction_theta_max 0.984 _diffrn_reflns_theta_full 25.20 _diffrn_measured_fraction_theta_full 0.984 _refine_diff_density_max 0.867 _refine_diff_density_min -0.622 _refine_diff_density_rms 0.104 # Attachment '- 1-Tb.cif' data_1-Tb _database_code_depnum_ccdc_archive 'CCDC 742767' #TrackingRef '- 1-Tb.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety '2(C7 H6 N2 O8 Tb), 10(H O0.50)' _chemical_formula_sum 'C14 H30 N4 O25 Tb2' _chemical_formula_weight 972.26 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Tb Tb -0.1723 4.1537 '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' _symmetry_space_group_name_Hall '-P 1' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 6.078(3) _cell_length_b 9.950(5) _cell_length_c 13.337(7) _cell_angle_alpha 68.823(6) _cell_angle_beta 81.142(7) _cell_angle_gamma 76.813(7) _cell_volume 730.0(6) _cell_formula_units_Z 1 _cell_measurement_temperature 298(2) _cell_measurement_reflns_used 690 _cell_measurement_theta_min 2.28 _cell_measurement_theta_max 19.74 _exptl_crystal_description block _exptl_crystal_colour colorless _exptl_crystal_size_max 0.16 _exptl_crystal_size_mid 0.12 _exptl_crystal_size_min 0.08 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 2.212 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 472 _exptl_absorpt_coefficient_mu 4.914 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.5069 _exptl_absorpt_correction_T_max 0.6946 _exptl_absorpt_process_details 'SADABS, Bruker(2002)' _exptl_special_details ; ? ; _diffrn_ambient_temperature 298(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type ? _diffrn_measurement_method ? _diffrn_detector_area_resol_mean ? _diffrn_reflns_number 3760 _diffrn_reflns_av_R_equivalents 0.0459 _diffrn_reflns_av_sigmaI/netI 0.0922 _diffrn_reflns_limit_h_min -7 _diffrn_reflns_limit_h_max 5 _diffrn_reflns_limit_k_min -11 _diffrn_reflns_limit_k_max 11 _diffrn_reflns_limit_l_min -15 _diffrn_reflns_limit_l_max 15 _diffrn_reflns_theta_min 1.64 _diffrn_reflns_theta_max 25.19 _reflns_number_total 2586 _reflns_number_gt 2072 _reflns_threshold_expression >2sigma(I) _computing_data_collection ? _computing_cell_refinement ? _computing_data_reduction ? _computing_structure_solution 'SHELXS-97 (Sheldrick, 2008)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _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^)+(0.1072P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 2586 _refine_ls_number_parameters 208 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0798 _refine_ls_R_factor_gt 0.0651 _refine_ls_wR_factor_ref 0.1651 _refine_ls_wR_factor_gt 0.1560 _refine_ls_goodness_of_fit_ref 0.980 _refine_ls_restrained_S_all 0.980 _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 Tb1 Tb 0.83363(10) 0.61393(6) 0.19546(4) 0.0238(2) Uani 1 1 d . . . C1 C 1.289(2) 0.7649(14) 0.1408(9) 0.024(3) Uani 1 1 d . . . C2 C 1.1348(18) 0.8928(13) 0.0697(8) 0.020(2) Uani 1 1 d . . . C3 C 0.811(2) 0.9704(13) -0.0150(9) 0.030(3) Uani 1 1 d . . . H3 H 0.6749 0.9537 -0.0279 0.036 Uiso 1 1 calc R . . C4 C 0.950(2) 0.3840(14) 0.4395(10) 0.033(3) Uani 1 1 d . . . C5 C 0.713(2) 0.4426(13) 0.4735(10) 0.026(3) Uani 1 1 d . . . C6 C 0.379(2) 0.6032(14) 0.4230(9) 0.027(3) Uani 1 1 d . . . H6 H 0.2913 0.6749 0.3706 0.033 Uiso 1 1 calc R . . C7 C 1.089(2) 0.4405(13) 0.0333(10) 0.031(3) Uani 1 1 d . . . N1 N 0.9378(17) 0.8624(11) 0.0541(8) 0.024(2) Uani 1 1 d . . . N2 N 0.5954(18) 0.5481(11) 0.3932(8) 0.029(2) Uani 1 1 d . . . O1 O 1.2152(15) 0.6475(9) 0.1835(8) 0.036(2) Uani 1 1 d . . . O2 O 1.4797(14) 0.7821(9) 0.1527(7) 0.0293(19) Uani 1 1 d . . . O3 O 1.0156(15) 0.4321(10) 0.3410(6) 0.036(2) Uani 1 1 d . . . O4 O 1.0702(17) 0.2882(11) 0.5105(7) 0.048(3) Uani 1 1 d . . . O5 O 1.0828(16) 0.4302(10) 0.1301(7) 0.036(2) Uani 1 1 d . . . O6 O 1.2237(14) 0.3620(9) -0.0127(7) 0.029(2) Uani 1 1 d . . . O1W O 0.8310(17) 0.7878(10) 0.2826(7) 0.037(2) Uani 1 1 d . . . H2W H 0.8720 0.7779 0.3434 0.056 Uiso 1 1 d R . . H1W H 0.7133 0.8547 0.2799 0.056 Uiso 1 1 d R . . O2W O 0.5990(16) 0.4364(10) 0.2194(7) 0.038(2) Uani 1 1 d . . . H3W H 0.4638 0.4856 0.2113 0.058 Uiso 1 1 d R . . H4W H 0.5735 0.3636 0.2708 0.058 Uiso 1 1 d R . . O3W O 0.640(2) 0.2809(19) 0.0850(12) 0.091(5) Uani 1 1 d . . . H5W H 0.6272 0.2003 0.1365 0.136 Uiso 1 1 d R . . H6W H 0.6921 0.2449 0.0346 0.136 Uiso 1 1 d R . . O4W O 0.515(3) 0.1926(18) 0.4138(12) 0.106(6) Uani 1 1 d . . . H8W H 0.4563 0.1309 0.4608 0.159 Uiso 1 1 d R . . H7W H 0.6330 0.1579 0.3939 0.159 Uiso 1 1 d R . . O5W O 0.536(4) 0.039(2) 0.2631(19) 0.167(11) Uani 1 1 d . . . H9W H 0.4802 -0.0169 0.3220 0.251 Uiso 1 1 d R . . H10W H 0.4152 0.1024 0.2436 0.251 Uiso 1 1 d R . . O6W O 0.060(5) 0.116(2) 0.268(2) 0.193(12) Uani 1 1 d . . . H12W H -0.0600 0.1252 0.2384 0.289 Uiso 1 1 d R . . H11W H 0.0630 0.2080 0.2490 0.289 Uiso 1 1 d R . . O7W O 0.087(7) -0.016(5) 0.513(6) 0.17(2) Uani 0.50 1 d P . . H13W H 0.0758 0.0046 0.4454 0.259 Uiso 0.50 1 d PR . . H14W H 0.1733 0.0454 0.5060 0.259 Uiso 0.50 1 d PR . . 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 0.0194(3) 0.0286(4) 0.0225(4) -0.0053(2) -0.0053(2) -0.0057(2) C1 0.019(6) 0.037(7) 0.015(6) -0.004(5) -0.003(5) -0.009(6) C2 0.014(5) 0.035(7) 0.010(5) -0.004(5) -0.005(4) -0.006(5) C3 0.034(7) 0.027(7) 0.019(6) 0.002(5) -0.003(5) 0.001(6) C4 0.033(7) 0.032(7) 0.027(7) -0.001(6) -0.007(6) -0.005(6) C5 0.029(7) 0.023(6) 0.029(7) -0.008(5) -0.010(5) -0.004(5) C6 0.020(6) 0.035(7) 0.022(6) -0.008(5) -0.003(5) 0.004(6) C7 0.035(7) 0.029(7) 0.025(7) -0.001(5) -0.002(6) -0.012(6) N1 0.020(5) 0.029(5) 0.025(5) -0.011(4) -0.005(4) -0.003(4) N2 0.028(6) 0.034(6) 0.029(6) -0.010(5) -0.003(5) -0.013(5) O1 0.018(4) 0.026(5) 0.050(6) 0.005(4) -0.017(4) -0.001(4) O2 0.020(4) 0.035(5) 0.032(5) -0.006(4) -0.007(4) -0.009(4) O3 0.028(5) 0.050(6) 0.017(4) 0.001(4) -0.002(4) -0.001(4) O4 0.040(6) 0.057(6) 0.031(5) -0.006(5) -0.014(5) 0.012(5) O5 0.040(5) 0.041(5) 0.026(5) -0.013(4) -0.004(4) -0.003(5) O6 0.023(4) 0.037(5) 0.032(5) -0.015(4) -0.007(4) -0.005(4) O1W 0.043(6) 0.039(5) 0.035(5) -0.015(4) -0.011(4) -0.008(5) O2W 0.035(5) 0.038(5) 0.039(5) -0.005(4) -0.005(4) -0.013(4) O3W 0.058(8) 0.150(14) 0.099(11) -0.089(11) -0.008(8) -0.008(9) O4W 0.080(11) 0.122(13) 0.075(10) -0.014(9) 0.010(8) 0.017(10) O5W 0.21(3) 0.102(14) 0.19(2) -0.070(15) -0.09(2) 0.060(16) O6W 0.18(3) 0.122(18) 0.22(3) -0.001(17) -0.03(2) -0.005(19) O7W 0.11(4) 0.08(3) 0.30(7) -0.03(3) -0.04(5) -0.01(3) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag Tb1 O3 2.341(8) . ? Tb1 O2 2.408(8) 1_455 ? Tb1 O1 2.391(9) . ? Tb1 O1W 2.404(9) . ? Tb1 O2W 2.420(9) . ? Tb1 O5 2.424(9) . ? Tb1 O6 2.433(8) 2_765 ? Tb1 N1 2.654(10) . ? Tb1 N2 2.737(10) . ? C1 O2 1.249(15) . ? C1 O1 1.254(15) . ? C1 C2 1.503(16) . ? C2 N1 1.362(15) . ? C2 C3 1.381(17) 2_775 ? C3 N1 1.314(15) . ? C3 H3 0.9300 . ? C4 O4 1.260(15) . ? C4 O3 1.259(15) . ? C4 C5 1.491(18) . ? C5 N2 1.357(15) . ? C5 C6 1.360(17) 2_666 ? C6 N2 1.361(15) . ? C6 C5 1.360(17) 2_666 ? C6 H6 0.9300 . ? C7 O5 1.253(15) . ? C7 O6 1.247(15) . ? C7 C7 1.52(2) 2_765 ? O2 Tb1 2.408(8) 1_655 ? O1W H2W 0.8507 . ? O1W H1W 0.8544 . ? O2W H3W 0.8560 . ? O2W H4W 0.8237 . ? O3W H5W 0.8570 . ? O3W H6W 0.8586 . ? O4W H8W 0.8052 . ? O4W H7W 0.7750 . ? O5W H9W 0.8572 . ? O5W H10W 0.8571 . ? O6W H12W 0.8543 . ? O6W H11W 0.8571 . ? O7W H13W 0.8601 . ? O7W H14W 0.8591 . ? 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 Tb1 O2 141.3(3) . 1_455 ? O3 Tb1 O1 71.4(3) . . ? O2 Tb1 O1 133.1(3) 1_455 . ? O3 Tb1 O1W 88.0(3) . . ? O2 Tb1 O1W 76.3(3) 1_455 . ? O1 Tb1 O1W 72.5(3) . . ? O3 Tb1 O2W 84.3(3) . . ? O2 Tb1 O2W 81.8(3) 1_455 . ? O1 Tb1 O2W 144.3(3) . . ? O1W Tb1 O2W 133.7(3) . . ? O3 Tb1 O5 71.6(3) . . ? O2 Tb1 O5 138.0(3) 1_455 . ? O1 Tb1 O5 71.5(3) . . ? O1W Tb1 O5 142.7(3) . . ? O2W Tb1 O5 76.3(3) . . ? O3 Tb1 O6 136.1(3) . 2_765 ? O2 Tb1 O6 74.1(3) 1_455 2_765 ? O1 Tb1 O6 104.0(3) . 2_765 ? O1W Tb1 O6 133.6(3) . 2_765 ? O2W Tb1 O6 75.7(3) . 2_765 ? O5 Tb1 O6 66.0(3) . 2_765 ? O3 Tb1 N1 133.0(3) . . ? O2 Tb1 N1 73.7(3) 1_455 . ? O1 Tb1 N1 62.9(3) . . ? O1W Tb1 N1 68.9(3) . . ? O2W Tb1 N1 141.1(3) . . ? O5 Tb1 N1 102.4(3) . . ? O6 Tb1 N1 68.9(3) 2_765 . ? O3 Tb1 N2 62.4(3) . . ? O2 Tb1 N2 78.9(3) 1_455 . ? O1 Tb1 N2 118.5(3) . . ? O1W Tb1 N2 67.7(3) . . ? O2W Tb1 N2 68.3(3) . . ? O5 Tb1 N2 123.3(3) . . ? O6 Tb1 N2 137.4(3) 2_765 . ? N1 Tb1 N2 132.8(3) . . ? O2 C1 O1 125.0(11) . . ? O2 C1 C2 118.6(11) . . ? O1 C1 C2 116.4(10) . . ? N1 C2 C3 120.3(11) . 2_775 ? N1 C2 C1 115.1(10) . . ? C3 C2 C1 124.4(11) 2_775 . ? N1 C3 C2 124.3(12) . 2_775 ? N1 C3 H3 117.8 . . ? C2 C3 H3 117.8 2_775 . ? O4 C4 O3 124.0(13) . . ? O4 C4 C5 118.1(12) . . ? O3 C4 C5 117.9(11) . . ? N2 C5 C6 121.9(11) . 2_666 ? N2 C5 C4 114.8(11) . . ? C6 C5 C4 123.3(11) 2_666 . ? N2 C6 C5 122.6(11) . 2_666 ? N2 C6 H6 118.7 . . ? C5 C6 H6 118.7 2_666 . ? O5 C7 O6 126.5(12) . . ? O5 C7 C7 116.0(14) . 2_765 ? O6 C7 C7 117.4(14) . 2_765 ? C3 N1 C2 115.3(11) . . ? C3 N1 Tb1 129.2(9) . . ? C2 N1 Tb1 114.3(7) . . ? C6 N2 C5 115.5(11) . . ? C6 N2 Tb1 130.4(8) . . ? C5 N2 Tb1 114.1(8) . . ? C1 O1 Tb1 127.6(7) . . ? C1 O2 Tb1 132.5(8) . 1_655 ? C4 O3 Tb1 130.8(8) . . ? C7 O5 Tb1 120.2(8) . . ? C7 O6 Tb1 119.4(8) . 2_765 ? Tb1 O1W H2W 132.3 . . ? Tb1 O1W H1W 118.1 . . ? H2W O1W H1W 99.0 . . ? Tb1 O2W H3W 105.5 . . ? Tb1 O2W H4W 132.2 . . ? H3W O2W H4W 99.7 . . ? H5W O3W H6W 98.1 . . ? H8W O4W H7W 110.4 . . ? H9W O5W H10W 98.1 . . ? H12W O6W H11W 97.5 . . ? H13W O7W H14W 97.2 . . ? _diffrn_measured_fraction_theta_max 0.985 _diffrn_reflns_theta_full 25.19 _diffrn_measured_fraction_theta_full 0.985 _refine_diff_density_max 3.829 _refine_diff_density_min -3.258 _refine_diff_density_rms 0.295 # Attachment '- 1-Dy.cif' data_1-Dy _database_code_depnum_ccdc_archive 'CCDC 742768' #TrackingRef '- 1-Dy.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety '2(C7 H6 Dy N2 O8), 10(H O0.50)' _chemical_formula_sum 'C14 H30 Dy2 N4 O25' _chemical_formula_weight 979.42 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' _symmetry_space_group_name_Hall '-P 1' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 6.0535(6) _cell_length_b 9.9159(9) _cell_length_c 13.2903(12) _cell_angle_alpha 68.8320(10) _cell_angle_beta 81.2730(10) _cell_angle_gamma 76.8750(10) _cell_volume 722.36(12) _cell_formula_units_Z 1 _cell_measurement_temperature 298(2) _cell_measurement_reflns_used 2045 _cell_measurement_theta_min 2.24 _cell_measurement_theta_max 27.86 _exptl_crystal_description block _exptl_crystal_colour colorless _exptl_crystal_size_max 0.23 _exptl_crystal_size_mid 0.16 _exptl_crystal_size_min 0.09 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 2.251 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 474 _exptl_absorpt_coefficient_mu 5.243 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.3785 _exptl_absorpt_correction_T_max 0.6498 _exptl_absorpt_process_details 'SADABS, Bruker(2002)' _exptl_special_details ; ? ; _diffrn_ambient_temperature 298(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type ? _diffrn_measurement_method ? _diffrn_detector_area_resol_mean ? _diffrn_reflns_number 3743 _diffrn_reflns_av_R_equivalents 0.0610 _diffrn_reflns_av_sigmaI/netI 0.0723 _diffrn_reflns_limit_h_min -7 _diffrn_reflns_limit_h_max 7 _diffrn_reflns_limit_k_min -11 _diffrn_reflns_limit_k_max 11 _diffrn_reflns_limit_l_min -15 _diffrn_reflns_limit_l_max 14 _diffrn_reflns_theta_min 1.65 _diffrn_reflns_theta_max 25.20 _reflns_number_total 2558 _reflns_number_gt 2248 _reflns_threshold_expression >2sigma(I) _computing_data_collection ? _computing_cell_refinement ? _computing_data_reduction ? _computing_structure_solution 'SHELXS-97 (Sheldrick, 2008)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _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^)+(0.0251P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 2558 _refine_ls_number_parameters 208 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0367 _refine_ls_R_factor_gt 0.0329 _refine_ls_wR_factor_ref 0.0730 _refine_ls_wR_factor_gt 0.0718 _refine_ls_goodness_of_fit_ref 0.973 _refine_ls_restrained_S_all 0.973 _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 0.83464(5) 0.61382(3) 0.19511(2) 0.01607(11) Uani 1 1 d . . . C1 C 1.2894(10) 0.7647(7) 0.1417(5) 0.0171(13) Uani 1 1 d . . . C2 C 1.1366(10) 0.8929(7) 0.0696(5) 0.0175(13) Uani 1 1 d . . . C3 C 0.8084(10) 0.9704(6) -0.0158(5) 0.0185(13) Uani 1 1 d . . . H3 H 0.6734 0.9524 -0.0292 0.022 Uiso 1 1 calc R . . C4 C 0.9508(11) 0.3817(7) 0.4387(5) 0.0230(14) Uani 1 1 d . . . C5 C 0.7108(10) 0.4448(7) 0.4719(5) 0.0212(14) Uani 1 1 d . . . C6 C 0.3818(11) 0.6040(7) 0.4231(5) 0.0230(15) Uani 1 1 d . . . H6 H 0.2945 0.6786 0.3714 0.028 Uiso 1 1 calc R . . C7 C 1.0892(10) 0.4390(7) 0.0343(5) 0.0198(14) Uani 1 1 d . . . N1 N 0.9389(8) 0.8639(5) 0.0539(4) 0.0171(11) Uani 1 1 d . . . N2 N 0.5930(9) 0.5479(5) 0.3930(4) 0.0224(12) Uani 1 1 d . . . O1 O 1.2162(7) 0.6469(5) 0.1840(4) 0.0276(11) Uani 1 1 d . . . O2 O 1.4834(7) 0.7811(5) 0.1525(3) 0.0215(10) Uani 1 1 d . . . O3 O 1.0156(8) 0.4325(5) 0.3406(4) 0.0298(11) Uani 1 1 d . . . O4 O 1.0718(8) 0.2894(5) 0.5093(4) 0.0376(13) Uani 1 1 d . . . O5 O 1.0843(7) 0.4293(5) 0.1308(4) 0.0283(11) Uani 1 1 d . . . O6 O 1.2257(7) 0.3612(5) -0.0132(4) 0.0258(10) Uani 1 1 d . . . O1W O 0.8332(8) 0.7866(5) 0.2825(4) 0.0292(11) Uani 1 1 d . . . H2W H 0.8742 0.7767 0.3433 0.044 Uiso 1 1 d R . . H1W H 0.7155 0.8535 0.2798 0.044 Uiso 1 1 d R . . O2W O 0.5990(7) 0.4368(5) 0.2192(4) 0.0259(10) Uani 1 1 d . . . H3W H 0.4672 0.4857 0.2112 0.039 Uiso 1 1 d R . . H4W H 0.5770 0.3636 0.2708 0.039 Uiso 1 1 d R . . O3W O 0.6392(10) 0.2767(9) 0.0873(6) 0.085(2) Uani 1 1 d . . . H5W H 0.6266 0.1961 0.1388 0.128 Uiso 1 1 d R . . H6W H 0.6915 0.2407 0.0369 0.128 Uiso 1 1 d R . . O4W O 0.5173(13) 0.1974(9) 0.4139(6) 0.098(3) Uani 1 1 d . . . H8W H 0.4686 0.1238 0.4625 0.147 Uiso 1 1 d R . . H7W H 0.6453 0.1508 0.3957 0.147 Uiso 1 1 d R . . O5W O 0.5316(18) 0.0344(9) 0.2672(9) 0.154(5) Uani 1 1 d . . . H9W H 0.4753 -0.0220 0.3261 0.231 Uiso 1 1 d R . . H10W H 0.4103 0.0974 0.2476 0.231 Uiso 1 1 d R . . O6W O 0.0703(19) 0.1166(11) 0.2707(9) 0.168(5) Uani 1 1 d . . . H12W H -0.0495 0.1254 0.2409 0.252 Uiso 1 1 d R . . H11W H 0.0735 0.2082 0.2515 0.252 Uiso 1 1 d R . . O7W O 0.084(3) -0.022(2) 0.513(3) 0.154(9) Uani 0.50 1 d P . . H14W H 0.0287 0.0709 0.4961 0.231 Uiso 0.50 1 d PR . . H13W H 0.1954 -0.0141 0.4633 0.231 Uiso 0.50 1 d PR . . 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 0.01193(17) 0.01797(17) 0.01578(17) -0.00252(12) -0.00236(11) -0.00228(11) C1 0.012(3) 0.024(3) 0.014(3) -0.007(3) 0.001(2) -0.002(3) C2 0.011(3) 0.025(3) 0.015(3) -0.006(3) -0.001(2) -0.005(3) C3 0.012(3) 0.019(3) 0.021(4) -0.001(3) -0.007(3) -0.002(3) C4 0.019(3) 0.026(4) 0.024(4) -0.009(3) 0.000(3) -0.006(3) C5 0.019(3) 0.024(3) 0.022(4) -0.008(3) -0.001(3) -0.006(3) C6 0.022(4) 0.023(4) 0.017(4) 0.002(3) -0.007(3) -0.003(3) C7 0.017(3) 0.021(3) 0.020(4) -0.007(3) -0.001(3) -0.003(3) N1 0.013(3) 0.021(3) 0.015(3) -0.002(2) -0.002(2) -0.003(2) N2 0.024(3) 0.019(3) 0.019(3) 0.001(2) -0.002(2) -0.004(2) O1 0.020(2) 0.022(2) 0.031(3) 0.006(2) -0.008(2) -0.005(2) O2 0.014(2) 0.023(2) 0.024(3) -0.004(2) -0.0059(18) -0.0036(18) O3 0.025(3) 0.035(3) 0.020(3) -0.001(2) -0.002(2) -0.002(2) O4 0.034(3) 0.047(3) 0.018(3) -0.002(2) -0.011(2) 0.011(2) O5 0.028(3) 0.033(3) 0.022(3) -0.012(2) -0.005(2) 0.005(2) O6 0.024(3) 0.030(3) 0.022(3) -0.012(2) -0.005(2) 0.003(2) O1W 0.034(3) 0.029(3) 0.024(3) -0.007(2) -0.010(2) -0.003(2) O2W 0.020(2) 0.018(2) 0.036(3) -0.003(2) -0.003(2) -0.0064(19) O3W 0.054(4) 0.131(7) 0.096(6) -0.081(6) -0.006(4) 0.004(4) O4W 0.095(6) 0.106(6) 0.077(6) -0.031(5) 0.006(5) 0.004(5) O5W 0.203(11) 0.075(6) 0.190(12) -0.066(7) -0.098(9) 0.055(7) O6W 0.179(12) 0.106(8) 0.173(12) 0.003(7) -0.037(9) -0.007(8) O7W 0.11(2) 0.068(13) 0.26(3) -0.031(15) -0.07(2) 0.014(14) _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 2.326(5) . ? Dy1 O1 2.381(4) . ? Dy1 O2 2.383(4) 1_455 ? Dy1 O1W 2.390(4) . ? Dy1 O2W 2.411(4) . ? Dy1 O6 2.415(4) 2_765 ? Dy1 O5 2.417(4) . ? Dy1 N1 2.657(5) . ? Dy1 N2 2.740(5) . ? C1 O1 1.250(7) . ? C1 O2 1.258(7) . ? C1 C2 1.499(8) . ? C2 N1 1.354(7) . ? C2 C3 1.376(8) 2_775 ? C3 N1 1.317(8) . ? C3 H3 0.9300 . ? C4 O4 1.241(8) . ? C4 O3 1.251(7) . ? C4 C5 1.513(8) . ? C5 N2 1.333(8) . ? C5 C6 1.375(8) 2_666 ? C6 N2 1.337(8) . ? C6 C5 1.375(8) 2_666 ? C6 H6 0.9300 . ? C7 O5 1.247(7) . ? C7 O6 1.257(7) . ? C7 C7 1.539(12) 2_765 ? O2 Dy1 2.383(4) 1_655 ? O1W H2W 0.8472 . ? O1W H1W 0.8517 . ? O2W H3W 0.8343 . ? O2W H4W 0.8196 . ? O3W H5W 0.8542 . ? O3W H6W 0.8562 . ? O4W H8W 0.8577 . ? O4W H7W 0.8570 . ? O5W H9W 0.8547 . ? O5W H10W 0.8539 . ? O6W H12W 0.8503 . ? O6W H11W 0.8541 . ? O7W H14W 0.8600 . ? O7W H13W 0.8600 . ? 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 O1 71.34(15) . . ? O3 Dy1 O2 141.16(15) . 1_455 ? O1 Dy1 O2 133.11(14) . 1_455 ? O3 Dy1 O1W 87.73(16) . . ? O1 Dy1 O1W 72.39(15) . . ? O2 Dy1 O1W 76.34(15) 1_455 . ? O3 Dy1 O2W 84.29(16) . . ? O1 Dy1 O2W 144.43(15) . . ? O2 Dy1 O2W 81.80(14) 1_455 . ? O1W Dy1 O2W 133.50(15) . . ? O3 Dy1 O6 136.54(15) . 2_765 ? O1 Dy1 O6 104.52(15) . 2_765 ? O2 Dy1 O6 73.74(14) 1_455 2_765 ? O1W Dy1 O6 133.53(15) . 2_765 ? O2W Dy1 O6 75.62(15) . 2_765 ? O3 Dy1 O5 71.36(15) . . ? O1 Dy1 O5 71.45(16) . . ? O2 Dy1 O5 138.34(15) 1_455 . ? O1W Dy1 O5 142.41(16) . . ? O2W Dy1 O5 76.48(15) . . ? O6 Dy1 O5 66.67(14) 2_765 . ? O3 Dy1 N1 132.97(16) . . ? O1 Dy1 N1 63.02(14) . . ? O2 Dy1 N1 73.54(14) 1_455 . ? O1W Dy1 N1 68.79(15) . . ? O2W Dy1 N1 141.26(15) . . ? O6 Dy1 N1 69.10(15) 2_765 . ? O5 Dy1 N1 102.85(15) . . ? O3 Dy1 N2 62.55(15) . . ? O1 Dy1 N2 118.69(16) . . ? O2 Dy1 N2 78.62(15) 1_455 . ? O1W Dy1 N2 67.83(15) . . ? O2W Dy1 N2 67.89(15) . . ? O6 Dy1 N2 136.69(15) 2_765 . ? O5 Dy1 N2 123.15(15) . . ? N1 Dy1 N2 132.62(14) . . ? O1 C1 O2 124.7(6) . . ? O1 C1 C2 116.9(5) . . ? O2 C1 C2 118.3(5) . . ? N1 C2 C3 120.3(6) . 2_775 ? N1 C2 C1 115.1(5) . . ? C3 C2 C1 124.5(5) 2_775 . ? N1 C3 C2 122.8(6) . 2_775 ? N1 C3 H3 118.6 . . ? C2 C3 H3 118.6 2_775 . ? O4 C4 O3 124.7(6) . . ? O4 C4 C5 118.9(6) . . ? O3 C4 C5 116.4(6) . . ? N2 C5 C6 122.1(6) . 2_666 ? N2 C5 C4 116.0(6) . . ? C6 C5 C4 121.9(6) 2_666 . ? N2 C6 C5 122.3(6) . 2_666 ? N2 C6 H6 118.9 . . ? C5 C6 H6 118.9 2_666 . ? O5 C7 O6 127.0(6) . . ? O5 C7 C7 116.3(6) . 2_765 ? O6 C7 C7 116.6(7) . 2_765 ? C3 N1 C2 117.0(5) . . ? C3 N1 Dy1 128.0(4) . . ? C2 N1 Dy1 114.0(4) . . ? C5 N2 C6 115.6(5) . . ? C5 N2 Dy1 113.4(4) . . ? C6 N2 Dy1 130.9(4) . . ? C1 O1 Dy1 127.2(4) . . ? C1 O2 Dy1 132.9(4) . 1_655 ? C4 O3 Dy1 131.7(4) . . ? C7 O5 Dy1 120.0(4) . . ? C7 O6 Dy1 119.4(4) . 2_765 ? Dy1 O1W H2W 132.5 . . ? Dy1 O1W H1W 117.9 . . ? H2W O1W H1W 98.9 . . ? Dy1 O2W H3W 105.0 . . ? Dy1 O2W H4W 131.1 . . ? H3W O2W H4W 101.3 . . ? H5W O3W H6W 98.1 . . ? H8W O4W H7W 98.0 . . ? H9W O5W H10W 98.1 . . ? H12W O6W H11W 97.4 . . ? H14W O7W H13W 97.2 . . ? _diffrn_measured_fraction_theta_max 0.982 _diffrn_reflns_theta_full 25.20 _diffrn_measured_fraction_theta_full 0.982 _refine_diff_density_max 1.248 _refine_diff_density_min -1.174 _refine_diff_density_rms 0.167 # Attachment '- 2-Eu.cif' data_eu _database_code_depnum_ccdc_archive 'CCDC 782471' #TrackingRef '- 2-Eu.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C9 H9 Eu N3 O9' _chemical_formula_sum 'C9 H9 Eu N3 O9' _chemical_formula_weight 455.15 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 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 monoclinic _symmetry_space_group_name_H-M 'P 21/c ' _symmetry_space_group_name_Hall '-P 2ybc ' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y-1/2, z-1/2' _cell_length_a 5.9950(5) _cell_length_b 19.0242(16) _cell_length_c 12.1311(8) _cell_angle_alpha 90.00 _cell_angle_beta 119.201(3) _cell_angle_gamma 90.00 _cell_volume 1207.72(16) _cell_formula_units_Z 4 _cell_measurement_temperature 298(2) _cell_measurement_reflns_used 4061 _cell_measurement_theta_min 2.88 _cell_measurement_theta_max 27.88 _exptl_crystal_description block _exptl_crystal_colour colorless _exptl_crystal_size_max 0.17 _exptl_crystal_size_mid 0.12 _exptl_crystal_size_min 0.05 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 2.503 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 876 _exptl_absorpt_coefficient_mu 5.253 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.4687 _exptl_absorpt_correction_T_max 0.7792 _exptl_absorpt_process_details 'SADABS, Bruker(2002)' _exptl_special_details ; ? ; _diffrn_ambient_temperature 298(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type ? _diffrn_measurement_method ? _diffrn_detector_area_resol_mean ? _diffrn_reflns_number 6544 _diffrn_reflns_av_R_equivalents 0.0363 _diffrn_reflns_av_sigmaI/netI 0.0305 _diffrn_reflns_limit_h_min -7 _diffrn_reflns_limit_h_max 7 _diffrn_reflns_limit_k_min -21 _diffrn_reflns_limit_k_max 23 _diffrn_reflns_limit_l_min -14 _diffrn_reflns_limit_l_max 14 _diffrn_reflns_theta_min 2.14 _diffrn_reflns_theta_max 25.99 _reflns_number_total 2349 _reflns_number_gt 2149 _reflns_threshold_expression >2sigma(I) _computing_data_collection ? _computing_cell_refinement ? _computing_data_reduction ? _computing_structure_solution 'SHELXS-97 (Sheldrick, 2008)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _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^)+(0.0251P)^2^+0.7404P] 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 2349 _refine_ls_number_parameters 199 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0235 _refine_ls_R_factor_gt 0.0208 _refine_ls_wR_factor_ref 0.0506 _refine_ls_wR_factor_gt 0.0495 _refine_ls_goodness_of_fit_ref 1.033 _refine_ls_restrained_S_all 1.033 _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 0.45478(3) 0.596852(8) 0.194693(14) 0.01409(7) Uani 1 1 d . . . C1 C 1.0078(6) 0.52628(16) 0.2704(3) 0.0163(7) Uani 1 1 d . . . C2 C 1.0085(6) 0.51238(16) 0.3937(3) 0.0162(6) Uani 1 1 d . . . C3 C 0.7959(6) 0.52260(16) 0.5055(3) 0.0168(7) Uani 1 1 d . . . H3 H 0.6561 0.5381 0.5124 0.020 Uiso 1 1 calc R . . C4 C 0.8571(7) 0.73610(19) 0.2832(3) 0.0226(7) Uani 1 1 d . . . C5 C 0.6005(7) 0.77220(17) 0.2128(3) 0.0219(7) Uani 1 1 d . . . C6 C 0.5616(8) 0.8444(2) 0.2022(4) 0.0347(9) Uani 1 1 d . . . H6 H 0.7025 0.8742 0.2373 0.042 Uiso 1 1 calc R . . C7 C 0.1322(8) 0.8272(2) 0.0949(4) 0.0331(9) Uani 1 1 d . . . H7 H -0.0335 0.8448 0.0555 0.040 Uiso 1 1 calc R . . C8 C 0.1674(7) 0.75547(18) 0.1016(3) 0.0222(7) Uani 1 1 d . . . C9 C -0.0434(7) 0.70199(19) 0.0483(3) 0.0236(8) Uani 1 1 d . . . N1 N 0.8013(5) 0.53482(13) 0.3988(3) 0.0160(6) Uani 1 1 d . . . N2 N 0.4024(5) 0.72856(14) 0.1621(3) 0.0193(6) Uani 1 1 d . . . N3 N 0.3279(7) 0.87222(17) 0.1430(4) 0.0410(9) Uani 1 1 d . . . O1 O 0.7930(4) 0.53821(12) 0.1779(2) 0.0216(5) Uani 1 1 d . . . O2 O 1.2187(5) 0.52455(13) 0.2730(2) 0.0235(5) Uani 1 1 d . . . O3 O 0.8463(5) 0.66962(12) 0.2895(2) 0.0254(6) Uani 1 1 d . . . O4 O 1.0538(5) 0.77198(15) 0.3289(3) 0.0325(6) Uani 1 1 d . . . O5 O 0.0246(5) 0.63843(13) 0.0667(2) 0.0268(6) Uani 1 1 d . . . O6 O -0.2698(5) 0.72339(14) -0.0091(3) 0.0317(6) Uani 1 1 d . . . O1W O 0.4333(5) 0.65570(12) 0.3744(2) 0.0273(6) Uani 1 1 d . . . H1W H 0.5107 0.6946 0.4054 0.041 Uiso 1 1 d R . . H2W H 0.2834 0.6677 0.3598 0.041 Uiso 1 1 d R . . O2W O 0.4056(5) 0.62335(13) -0.0142(2) 0.0251(5) Uani 1 1 d . . . H3W H 0.5270 0.6510 -0.0053 0.038 Uiso 1 1 d R . . H4W H 0.2785 0.6493 -0.0631 0.038 Uiso 1 1 d R . . O3W O 0.2777(6) 0.49340(15) 0.0643(3) 0.0501(9) Uani 1 1 d . . . H5W H 0.2816 0.4860 -0.0042 0.075 Uiso 1 1 d R . . H6W H 0.1991 0.4563 0.0658 0.075 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 0.01445(11) 0.01459(10) 0.01256(10) 0.00080(6) 0.00605(8) 0.00096(6) C1 0.0217(18) 0.0121(15) 0.0193(17) -0.0010(13) 0.0132(15) -0.0003(12) C2 0.0183(17) 0.0142(15) 0.0166(16) -0.0001(13) 0.0088(14) -0.0002(13) C3 0.0187(17) 0.0165(16) 0.0178(17) 0.0029(13) 0.0109(14) 0.0009(13) C4 0.0229(19) 0.0281(19) 0.0190(17) -0.0039(15) 0.0119(15) -0.0019(15) C5 0.0257(19) 0.0206(17) 0.0209(18) -0.0021(14) 0.0124(16) -0.0030(14) C6 0.037(2) 0.023(2) 0.038(2) -0.0019(17) 0.013(2) -0.0064(17) C7 0.029(2) 0.025(2) 0.039(2) 0.0051(17) 0.0110(19) 0.0060(16) C8 0.0238(19) 0.0241(18) 0.0204(18) 0.0037(14) 0.0121(16) 0.0044(14) C9 0.0209(19) 0.030(2) 0.0229(18) 0.0083(15) 0.0128(16) 0.0033(15) N1 0.0172(14) 0.0145(13) 0.0165(14) 0.0017(11) 0.0082(12) -0.0007(11) N2 0.0187(15) 0.0185(14) 0.0222(15) 0.0005(12) 0.0111(12) 0.0000(11) N3 0.043(2) 0.0197(17) 0.051(2) 0.0038(16) 0.0156(19) 0.0074(15) O1 0.0199(13) 0.0288(13) 0.0159(12) 0.0015(10) 0.0086(11) 0.0046(10) O2 0.0201(13) 0.0304(13) 0.0234(13) 0.0052(11) 0.0134(11) 0.0023(10) O3 0.0212(13) 0.0224(13) 0.0276(14) 0.0004(10) 0.0081(11) 0.0028(10) O4 0.0233(15) 0.0383(16) 0.0339(16) -0.0103(12) 0.0124(13) -0.0121(11) O5 0.0208(13) 0.0235(13) 0.0313(15) 0.0078(11) 0.0090(12) 0.0015(10) O6 0.0210(14) 0.0350(15) 0.0370(16) 0.0134(12) 0.0125(12) 0.0075(11) O1W 0.0305(15) 0.0253(13) 0.0285(15) -0.0023(11) 0.0163(12) 0.0023(11) O2W 0.0271(14) 0.0267(13) 0.0198(13) 0.0044(11) 0.0101(11) 0.0021(11) O3W 0.074(2) 0.0444(18) 0.060(2) -0.0359(16) 0.055(2) -0.0355(16) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag Eu1 O5 2.404(2) . ? Eu1 O1 2.408(2) . ? Eu1 O3W 2.422(3) . ? Eu1 O2W 2.456(2) . ? Eu1 O3 2.473(2) . ? Eu1 O2 2.472(2) 1_455 ? Eu1 O1W 2.509(2) . ? Eu1 N2 2.532(3) . ? Eu1 N1 2.612(3) . ? C1 O1 1.249(4) . ? C1 O2 1.249(4) . ? C1 C2 1.517(4) . ? C2 N1 1.343(4) . ? C2 C3 1.384(5) 3_766 ? C3 N1 1.330(4) . ? C3 C2 1.384(5) 3_766 ? C3 H3 0.9300 . ? C4 O4 1.236(4) . ? C4 O3 1.271(4) . ? C4 C5 1.512(5) . ? C5 N2 1.329(4) . ? C5 C6 1.389(5) . ? C6 N3 1.333(6) . ? C6 H6 0.9300 . ? C7 N3 1.336(5) . ? C7 C8 1.376(5) . ? C7 H7 0.9300 . ? C8 N2 1.333(4) . ? C8 C9 1.501(5) . ? C9 O6 1.253(4) . ? C9 O5 1.261(4) . ? O2 Eu1 2.472(2) 1_655 ? O1W H1W 0.8568 . ? O1W H2W 0.8576 . ? O2W H3W 0.8612 . ? O2W H4W 0.8571 . ? O3W H5W 0.8542 . ? O3W H6W 0.8545 . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag O5 Eu1 O1 141.24(8) . . ? O5 Eu1 O3W 81.68(11) . . ? O1 Eu1 O3W 71.76(9) . . ? O5 Eu1 O2W 73.44(8) . . ? O1 Eu1 O2W 71.95(8) . . ? O3W Eu1 O2W 72.48(9) . . ? O5 Eu1 O3 126.29(8) . . ? O1 Eu1 O3 69.62(8) . . ? O3W Eu1 O3 140.63(9) . . ? O2W Eu1 O3 88.52(8) . . ? O5 Eu1 O2 78.26(8) . 1_455 ? O1 Eu1 O2 116.00(8) . 1_455 ? O3W Eu1 O2 69.41(9) . 1_455 ? O2W Eu1 O2 135.05(8) . 1_455 ? O3 Eu1 O2 136.39(8) . 1_455 ? O5 Eu1 O1W 85.46(9) . . ? O1 Eu1 O1W 133.03(8) . . ? O3W Eu1 O1W 137.58(8) . . ? O2W Eu1 O1W 140.67(8) . . ? O3 Eu1 O1W 77.60(8) . . ? O2 Eu1 O1W 68.44(8) 1_455 . ? O5 Eu1 N2 63.98(9) . . ? O1 Eu1 N2 119.38(8) . . ? O3W Eu1 N2 136.12(11) . . ? O2W Eu1 N2 72.10(9) . . ? O3 Eu1 N2 62.35(8) . . ? O2 Eu1 N2 124.04(8) 1_455 . ? O1W Eu1 N2 68.84(8) . . ? O5 Eu1 N1 150.16(8) . . ? O1 Eu1 N1 63.77(8) . . ? O3W Eu1 N1 98.32(10) . . ? O2W Eu1 N1 135.28(8) . . ? O3 Eu1 N1 71.12(8) . . ? O2 Eu1 N1 73.97(8) 1_455 . ? O1W Eu1 N1 74.46(8) . . ? N2 Eu1 N1 125.15(9) . . ? O5 Eu1 C1 159.83(8) . . ? O1 Eu1 C1 18.63(8) . . ? O3W Eu1 C1 84.89(10) . . ? O2W Eu1 C1 88.22(8) . . ? O3 Eu1 C1 59.77(8) . . ? O2 Eu1 C1 110.87(8) 1_455 . ? O1W Eu1 C1 114.49(8) . . ? N2 Eu1 C1 118.84(8) . . ? N1 Eu1 C1 47.07(8) . . ? O1 C1 O2 127.9(3) . . ? O1 C1 C2 115.1(3) . . ? O2 C1 C2 117.0(3) . . ? O2 C1 Eu1 153.3(2) . . ? C2 C1 Eu1 82.13(17) . . ? N1 C2 C3 121.1(3) . 3_766 ? N1 C2 C1 115.6(3) . . ? C3 C2 C1 123.3(3) 3_766 . ? N1 C3 C2 122.1(3) . 3_766 ? N1 C3 H3 118.9 . . ? C2 C3 H3 118.9 3_766 . ? O4 C4 O3 126.0(3) . . ? O4 C4 C5 119.2(3) . . ? O3 C4 C5 114.7(3) . . ? N2 C5 C6 120.3(3) . . ? N2 C5 C4 114.3(3) . . ? C6 C5 C4 125.5(3) . . ? N3 C6 C5 121.8(4) . . ? N3 C6 H6 119.1 . . ? C5 C6 H6 119.1 . . ? N3 C7 C8 122.2(4) . . ? N3 C7 H7 118.9 . . ? C8 C7 H7 118.9 . . ? N2 C8 C7 120.3(3) . . ? N2 C8 C9 114.7(3) . . ? C7 C8 C9 125.0(3) . . ? O6 C9 O5 125.4(3) . . ? O6 C9 C8 118.4(3) . . ? O5 C9 C8 116.2(3) . . ? C3 N1 C2 116.8(3) . . ? C3 N1 Eu1 128.0(2) . . ? C2 N1 Eu1 115.2(2) . . ? C5 N2 C8 118.7(3) . . ? C5 N2 Eu1 122.1(2) . . ? C8 N2 Eu1 118.9(2) . . ? C7 N3 C6 116.7(3) . . ? C1 O1 Eu1 123.35(19) . . ? C1 O2 Eu1 137.5(2) . 1_655 ? C4 O3 Eu1 126.4(2) . . ? C9 O5 Eu1 125.6(2) . . ? Eu1 O1W H1W 121.4 . . ? Eu1 O1W H2W 115.6 . . ? H1W O1W H2W 98.5 . . ? Eu1 O2W H3W 109.1 . . ? Eu1 O2W H4W 116.8 . . ? H3W O2W H4W 98.4 . . ? Eu1 O3W H5W 123.9 . . ? Eu1 O3W H6W 136.8 . . ? H5W O3W H6W 99.3 . . ? loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA _geom_hbond_site_symmetry_A O3W H6W O5 0.85 2.35 3.048(4) 139.1 3_565 O3W H5W O1 0.85 1.98 2.821(4) 166.6 3_665 O2W H4W O4 0.86 2.01 2.849(4) 164.9 4_475 O2W H3W O6 0.86 1.85 2.701(4) 167.5 1_655 O1W H2W O4 0.86 2.34 3.025(4) 137.3 1_455 O1W H2W O3 0.86 2.33 3.159(4) 163.5 1_455 O1W H1W O6 0.86 1.98 2.829(4) 172.3 4_676 _diffrn_measured_fraction_theta_max 0.992 _diffrn_reflns_theta_full 25.99 _diffrn_measured_fraction_theta_full 0.992 _refine_diff_density_max 1.147 _refine_diff_density_min -0.865 _refine_diff_density_rms 0.111 # Attachment '- 2-Pr.cif' data_2-Pr _database_code_depnum_ccdc_archive 'CCDC 782472' #TrackingRef '- 2-Pr.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C9 H9 N3 O9 Pr' _chemical_formula_sum 'C9 H9 N3 O9 Pr' _chemical_formula_weight 444.10 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' Pr Pr -0.2180 2.8214 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M 'P 21/c ' _symmetry_space_group_name_Hall '-P 2ybc ' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y-1/2, z-1/2' _cell_length_a 6.002(2) _cell_length_b 19.161(7) _cell_length_c 12.255(4) _cell_angle_alpha 90.00 _cell_angle_beta 118.793(13) _cell_angle_gamma 90.00 _cell_volume 1235.1(7) _cell_formula_units_Z 4 _cell_measurement_temperature 298(2) _cell_measurement_reflns_used 3021 _cell_measurement_theta_min 2.17 _cell_measurement_theta_max 27.58 _exptl_crystal_description block _exptl_crystal_colour colorless _exptl_crystal_size_max 0.23 _exptl_crystal_size_mid 0.16 _exptl_crystal_size_min 0.11 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 2.388 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 860 _exptl_absorpt_coefficient_mu 4.003 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.4595 _exptl_absorpt_correction_T_max 0.6672 _exptl_absorpt_process_details 'SADABS, Bruker(2002)' _exptl_special_details ; ? ; _diffrn_ambient_temperature 298(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type ? _diffrn_measurement_method ? _diffrn_detector_area_resol_mean ? _diffrn_reflns_number 6019 _diffrn_reflns_av_R_equivalents 0.0990 _diffrn_reflns_av_sigmaI/netI 0.0816 _diffrn_reflns_limit_h_min -7 _diffrn_reflns_limit_h_max 7 _diffrn_reflns_limit_k_min -22 _diffrn_reflns_limit_k_max 16 _diffrn_reflns_limit_l_min -14 _diffrn_reflns_limit_l_max 13 _diffrn_reflns_theta_min 2.13 _diffrn_reflns_theta_max 25.10 _reflns_number_total 2180 _reflns_number_gt 1921 _reflns_threshold_expression >2sigma(I) _computing_data_collection ? _computing_cell_refinement ? _computing_data_reduction ? _computing_structure_solution 'SHELXS-97 (Sheldrick, 2008)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _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^)+(0.0394P)^2^+6.7406P] 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 2180 _refine_ls_number_parameters 199 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0528 _refine_ls_R_factor_gt 0.0468 _refine_ls_wR_factor_ref 0.1140 _refine_ls_wR_factor_gt 0.1113 _refine_ls_goodness_of_fit_ref 1.085 _refine_ls_restrained_S_all 1.085 _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 Pr1 Pr 0.44932(7) 0.59630(2) 0.19309(3) 0.02091(18) Uani 1 1 d . . . C1 C 1.0107(14) 0.5245(4) 0.2739(6) 0.0219(16) Uani 1 1 d . . . C2 C 1.0096(13) 0.5115(4) 0.3953(6) 0.0194(15) Uani 1 1 d . . . C3 C 0.7980(14) 0.5239(4) 0.5054(6) 0.0214(16) Uani 1 1 d . . . H3 H 0.6604 0.5407 0.5128 0.026 Uiso 1 1 calc R . . C4 C 0.8461(14) 0.7393(4) 0.2792(7) 0.0255(17) Uani 1 1 d . . . C5 C 0.5840(15) 0.7735(4) 0.2087(7) 0.0276(17) Uani 1 1 d . . . C6 C 0.5430(19) 0.8450(5) 0.1978(8) 0.042(2) Uani 1 1 d . . . H6 H 0.6821 0.8749 0.2342 0.051 Uiso 1 1 calc R . . C7 C 0.1192(18) 0.8266(5) 0.0900(9) 0.040(2) Uani 1 1 d . . . H7 H -0.0465 0.8435 0.0498 0.047 Uiso 1 1 calc R . . C8 C 0.1578(15) 0.7557(4) 0.0987(7) 0.0307(18) Uani 1 1 d . . . C9 C -0.0527(14) 0.7028(4) 0.0456(7) 0.0272(17) Uani 1 1 d . . . N1 N 0.8052(12) 0.5345(3) 0.4012(5) 0.0239(14) Uani 1 1 d . . . N2 N 0.3913(12) 0.7309(3) 0.1581(6) 0.0240(14) Uani 1 1 d . . . N3 N 0.3123(16) 0.8720(4) 0.1376(8) 0.048(2) Uani 1 1 d . . . O1 O 0.8008(10) 0.5368(3) 0.1824(4) 0.0282(12) Uani 1 1 d . . . O2 O 1.2217(10) 0.5211(3) 0.2752(5) 0.0285(12) Uani 1 1 d . . . O3 O 0.8391(10) 0.6733(3) 0.2858(5) 0.0328(13) Uani 1 1 d . . . O4 O 1.0343(11) 0.7754(3) 0.3233(6) 0.0419(16) Uani 1 1 d . . . O5 O 0.0149(10) 0.6399(3) 0.0626(5) 0.0319(13) Uani 1 1 d . . . O6 O -0.2786(10) 0.7248(3) -0.0110(5) 0.0365(14) Uani 1 1 d . . . O1W O 0.4181(12) 0.6574(3) 0.3730(5) 0.0365(14) Uani 1 1 d . . . H1W H 0.4955 0.6964 0.4041 0.055 Uiso 1 1 d R . . H2W H 0.2682 0.6695 0.3584 0.055 Uiso 1 1 d R . . O2W O 0.3976(11) 0.6241(3) -0.0194(5) 0.0311(13) Uani 1 1 d . . . H3W H 0.5190 0.6518 -0.0106 0.047 Uiso 1 1 d R . . H4W H 0.2706 0.6500 -0.0683 0.047 Uiso 1 1 d R . . O3W O 0.2796(16) 0.4908(4) 0.0614(7) 0.068(3) Uani 1 1 d . . . H5W H 0.2834 0.4834 -0.0071 0.102 Uiso 1 1 d R . . H6W H 0.2010 0.4537 0.0629 0.102 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 Pr1 0.0179(3) 0.0230(3) 0.0250(2) 0.00108(16) 0.01293(18) 0.00118(16) C1 0.027(4) 0.018(4) 0.023(4) 0.001(3) 0.014(3) 0.000(3) C2 0.015(3) 0.020(4) 0.027(4) -0.001(3) 0.013(3) 0.000(3) C3 0.018(4) 0.024(4) 0.024(3) 0.000(3) 0.011(3) -0.002(3) C4 0.024(4) 0.030(4) 0.024(4) -0.003(3) 0.013(3) -0.003(3) C5 0.033(4) 0.022(4) 0.028(4) 0.000(3) 0.016(3) -0.003(3) C6 0.043(5) 0.036(5) 0.049(5) -0.009(4) 0.024(4) -0.011(4) C7 0.036(5) 0.030(5) 0.058(5) 0.007(4) 0.026(4) 0.007(4) C8 0.030(4) 0.030(5) 0.035(4) 0.009(3) 0.018(4) 0.005(3) C9 0.024(4) 0.031(4) 0.030(4) 0.007(3) 0.015(3) 0.000(3) N1 0.019(3) 0.027(3) 0.025(3) 0.000(3) 0.011(3) -0.001(3) N2 0.024(3) 0.023(3) 0.032(3) 0.002(3) 0.020(3) 0.004(3) N3 0.050(5) 0.025(4) 0.063(5) 0.006(4) 0.023(4) 0.008(4) O1 0.026(3) 0.036(3) 0.026(3) 0.003(2) 0.015(2) 0.005(2) O2 0.025(3) 0.036(3) 0.034(3) 0.004(2) 0.022(2) 0.002(2) O3 0.022(3) 0.035(3) 0.038(3) 0.001(3) 0.013(2) 0.003(2) O4 0.028(3) 0.052(4) 0.047(3) -0.011(3) 0.020(3) -0.015(3) O5 0.024(3) 0.024(3) 0.046(3) 0.006(2) 0.016(3) 0.000(2) O6 0.023(3) 0.043(4) 0.049(3) 0.016(3) 0.021(3) 0.009(3) O1W 0.039(3) 0.036(3) 0.041(3) -0.007(3) 0.024(3) 0.002(3) O2W 0.030(3) 0.033(3) 0.030(3) 0.004(2) 0.015(2) 0.000(2) O3W 0.111(7) 0.053(4) 0.094(6) -0.044(4) 0.093(5) -0.050(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 Pr1 O1 2.457(6) . ? Pr1 O5 2.457(5) . ? Pr1 O3W 2.479(6) . ? Pr1 O2 2.506(5) 1_455 ? Pr1 O2W 2.527(5) . ? Pr1 O3 2.526(6) . ? Pr1 O1W 2.582(6) . ? Pr1 N2 2.610(6) . ? Pr1 N1 2.687(6) . ? C1 O1 1.241(9) . ? C1 O2 1.261(9) . ? C1 C2 1.512(10) . ? C2 N1 1.337(10) . ? C2 C3 1.387(10) 3_766 ? C3 N1 1.315(10) . ? C3 C2 1.387(10) 3_766 ? C3 H3 0.9300 . ? C4 O4 1.208(9) . ? C4 O3 1.269(9) . ? C4 C5 1.530(11) . ? C5 N2 1.304(10) . ? C5 C6 1.387(12) . ? C6 N3 1.321(13) . ? C6 H6 0.9300 . ? C7 N3 1.338(12) . ? C7 C8 1.372(12) . ? C7 H7 0.9300 . ? C8 N2 1.319(10) . ? C8 C9 1.502(11) . ? C9 O6 1.261(10) . ? C9 O5 1.257(10) . ? O2 Pr1 2.506(5) 1_655 ? O1W H1W 0.8636 . ? O1W H2W 0.8597 . ? O2W H3W 0.8645 . ? O2W H4W 0.8645 . ? O3W H5W 0.8626 . ? O3W H6W 0.8590 . ? 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 Pr1 O5 142.41(18) . . ? O1 Pr1 O3W 71.4(2) . . ? O5 Pr1 O3W 83.0(3) . . ? O1 Pr1 O2 113.75(18) . 1_455 ? O5 Pr1 O2 81.03(18) . 1_455 ? O3W Pr1 O2 70.1(2) . 1_455 ? O1 Pr1 O2W 74.04(18) . . ? O5 Pr1 O2W 72.1(2) . . ? O3W Pr1 O2W 72.1(2) . . ? O2 Pr1 O2W 135.65(18) 1_455 . ? O1 Pr1 O3 70.25(19) . . ? O5 Pr1 O3 123.83(17) . . ? O3W Pr1 O3 140.4(2) . . ? O2 Pr1 O3 136.15(18) 1_455 . ? O2W Pr1 O3 88.16(19) . . ? O1 Pr1 O1W 132.35(17) . . ? O5 Pr1 O1W 84.9(2) . . ? O3W Pr1 O1W 138.6(2) . . ? O2 Pr1 O1W 68.93(19) 1_455 . ? O2W Pr1 O1W 139.55(18) . . ? O3 Pr1 O1W 77.5(2) . . ? O1 Pr1 N2 119.99(19) . . ? O5 Pr1 N2 62.71(18) . . ? O3W Pr1 N2 135.9(2) . . ? O2 Pr1 N2 125.37(19) 1_455 . ? O2W Pr1 N2 71.46(19) . . ? O3 Pr1 N2 61.18(18) . . ? O1W Pr1 N2 68.47(19) . . ? O1 Pr1 N1 62.34(18) . . ? O5 Pr1 N1 151.3(2) . . ? O3W Pr1 N1 98.5(2) . . ? O2 Pr1 N1 72.75(19) 1_455 . ? O2W Pr1 N1 135.9(2) . . ? O3 Pr1 N1 71.93(19) . . ? O1W Pr1 N1 74.99(19) . . ? N2 Pr1 N1 124.98(19) . . ? O1 C1 O2 126.7(7) . . ? O1 C1 C2 115.9(7) . . ? O2 C1 C2 117.4(6) . . ? N1 C2 C3 120.8(7) . 3_766 ? N1 C2 C1 115.9(6) . . ? C3 C2 C1 123.2(7) 3_766 . ? N1 C3 C2 121.6(7) . 3_766 ? N1 C3 H3 119.2 . . ? C2 C3 H3 119.2 3_766 . ? O4 C4 O3 126.5(8) . . ? O4 C4 C5 119.5(7) . . ? O3 C4 C5 114.0(7) . . ? N2 C5 C6 119.8(8) . . ? N2 C5 C4 115.8(7) . . ? C6 C5 C4 124.4(7) . . ? N3 C6 C5 122.1(9) . . ? N3 C6 H6 119.0 . . ? C5 C6 H6 119.0 . . ? N3 C7 C8 122.1(9) . . ? N3 C7 H7 119.0 . . ? C8 C7 H7 119.0 . . ? N2 C8 C7 119.7(8) . . ? N2 C8 C9 116.3(7) . . ? C7 C8 C9 124.0(8) . . ? O6 C9 O5 125.9(7) . . ? O6 C9 C8 118.0(7) . . ? O5 C9 C8 116.0(7) . . ? C3 N1 C2 117.5(6) . . ? C3 N1 Pr1 127.4(5) . . ? C2 N1 Pr1 115.1(5) . . ? C5 N2 C8 120.0(7) . . ? C5 N2 Pr1 121.6(5) . . ? C8 N2 Pr1 118.0(5) . . ? C6 N3 C7 116.3(8) . . ? C1 O1 Pr1 124.3(5) . . ? C1 O2 Pr1 134.7(5) . 1_655 ? C4 O3 Pr1 127.3(5) . . ? C9 O5 Pr1 126.2(5) . . ? Pr1 O1W H1W 121.5 . . ? Pr1 O1W H2W 116.3 . . ? H1W O1W H2W 98.5 . . ? Pr1 O2W H3W 108.8 . . ? Pr1 O2W H4W 117.7 . . ? H3W O2W H4W 98.2 . . ? Pr1 O3W H5W 124.9 . . ? Pr1 O3W H6W 136.0 . . ? H5W O3W H6W 99.0 . . ? loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA _geom_hbond_site_symmetry_A O1W H1W O6 0.86 1.96 2.817(8) 170.6 4_676 O1W H2W O3 0.86 2.29 3.120(8) 163.7 1_455 O1W H2W O4 0.86 2.39 3.071(9) 137.0 1_455 O2W H3W O6 0.86 1.85 2.705(8) 167.4 1_655 O2W H4W O4 0.86 2.00 2.851(8) 167.8 4_475 O3W H5W O1 0.86 1.99 2.837(9) 165.7 3_665 O3W H6W O5 0.86 2.31 3.020(8) 140.1 3_565 _diffrn_measured_fraction_theta_max 0.993 _diffrn_reflns_theta_full 25.10 _diffrn_measured_fraction_theta_full 0.993 _refine_diff_density_max 2.965 _refine_diff_density_min -0.963 _refine_diff_density_rms 0.211 # Attachment '- 2-Sm.cif' data_2-Sm _database_code_depnum_ccdc_archive 'CCDC 782473' #TrackingRef '- 2-Sm.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C9 H9 N3 O9 Sm' _chemical_formula_sum 'C9 H9 N3 O9 Sm' _chemical_formula_weight 453.54 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' Sm Sm -0.1638 3.4418 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Monoclinic _symmetry_space_group_name_H-M 'P 21/c' _symmetry_space_group_name_Hall '-P 2ybc' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y-1/2, z-1/2' _cell_length_a 6.0008(4) _cell_length_b 19.0754(14) _cell_length_c 12.1796(7) _cell_angle_alpha 90.00 _cell_angle_beta 119.050(3) _cell_angle_gamma 90.00 _cell_volume 1218.78(14) _cell_formula_units_Z 4 _cell_measurement_temperature 298(2) _cell_measurement_reflns_used 4389 _cell_measurement_theta_min 2.87 _cell_measurement_theta_max 27.84 _exptl_crystal_description block _exptl_crystal_colour colorless _exptl_crystal_size_max 0.17 _exptl_crystal_size_mid 0.12 _exptl_crystal_size_min 0.05 _exptl_crystal_density_meas s _exptl_crystal_density_diffrn 2.472 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 872 _exptl_absorpt_coefficient_mu 4.877 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.4911 _exptl_absorpt_correction_T_max 0.7925 _exptl_absorpt_process_details SADABS,Bruker(2002) _exptl_special_details ; ? ; _diffrn_ambient_temperature 298(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type ? _diffrn_measurement_method ? _diffrn_detector_area_resol_mean ? _diffrn_reflns_number 6364 _diffrn_reflns_av_R_equivalents 0.0595 _diffrn_reflns_av_sigmaI/netI 0.0429 _diffrn_reflns_limit_h_min -7 _diffrn_reflns_limit_h_max 7 _diffrn_reflns_limit_k_min -19 _diffrn_reflns_limit_k_max 23 _diffrn_reflns_limit_l_min -14 _diffrn_reflns_limit_l_max 14 _diffrn_reflns_theta_min 2.14 _diffrn_reflns_theta_max 25.50 _reflns_number_total 2262 _reflns_number_gt 2043 _reflns_threshold_expression >2sigma(I) _computing_data_collection ? _computing_cell_refinement ? _computing_data_reduction ? _computing_structure_solution 'SHELXS-97 (Sheldrick, 2008)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _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^)+(0.0409P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 2262 _refine_ls_number_parameters 199 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0299 _refine_ls_R_factor_gt 0.0275 _refine_ls_wR_factor_ref 0.0685 _refine_ls_wR_factor_gt 0.0673 _refine_ls_goodness_of_fit_ref 1.018 _refine_ls_restrained_S_all 1.018 _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 Sm1 Sm 0.45280(4) 0.596645(9) 0.194294(17) 0.01337(10) Uani 1 1 d . . . C1 C 1.0085(7) 0.5257(2) 0.2723(4) 0.0149(8) Uani 1 1 d . . . C2 C 1.0087(7) 0.51221(19) 0.3944(3) 0.0137(8) Uani 1 1 d . . . C3 C 0.7957(7) 0.52268(19) 0.5058(3) 0.0150(8) Uani 1 1 d . . . H3 H 0.6561 0.5380 0.5129 0.018 Uiso 1 1 calc R . . C4 C 0.8524(8) 0.7373(2) 0.2820(4) 0.0212(9) Uani 1 1 d . . . C5 C 0.5949(8) 0.7728(2) 0.2113(4) 0.0208(9) Uani 1 1 d . . . C6 C 0.5547(10) 0.8447(2) 0.2003(4) 0.0321(11) Uani 1 1 d . . . H6 H 0.6950 0.8745 0.2350 0.039 Uiso 1 1 calc R . . C7 C 0.1280(9) 0.8270(2) 0.0931(4) 0.0312(11) Uani 1 1 d . . . H7 H -0.0377 0.8444 0.0527 0.037 Uiso 1 1 calc R . . C8 C 0.1639(8) 0.7556(2) 0.1005(4) 0.0208(9) Uani 1 1 d . . . C9 C -0.0475(8) 0.7020(2) 0.0477(4) 0.0199(9) Uani 1 1 d . . . N1 N 0.8023(6) 0.53496(16) 0.3995(3) 0.0134(6) Uani 1 1 d . . . N2 N 0.3977(6) 0.72865(17) 0.1604(3) 0.0177(7) Uani 1 1 d . . . N3 N 0.3218(8) 0.8724(2) 0.1417(4) 0.0395(10) Uani 1 1 d . . . O1 O 0.7946(5) 0.53747(15) 0.1787(2) 0.0204(6) Uani 1 1 d . . . O2 O 1.2192(5) 0.52354(16) 0.2738(3) 0.0220(6) Uani 1 1 d . . . O3 O 0.8444(5) 0.67084(15) 0.2885(3) 0.0231(6) Uani 1 1 d . . . O4 O 1.0466(6) 0.77345(18) 0.3270(3) 0.0326(8) Uani 1 1 d . . . O5 O 0.0206(5) 0.63903(15) 0.0654(3) 0.0254(7) Uani 1 1 d . . . O6 O -0.2721(6) 0.72353(17) -0.0101(3) 0.0309(7) Uani 1 1 d . . . O1W O 0.4283(6) 0.65623(15) 0.3745(3) 0.0271(7) Uani 1 1 d . . . H1W H 0.5057 0.6951 0.4055 0.041 Uiso 1 1 d R . . H2W H 0.2785 0.6682 0.3599 0.041 Uiso 1 1 d R . . O2W O 0.4036(6) 0.62358(16) -0.0155(3) 0.0241(6) Uani 1 1 d . . . H3W H 0.5250 0.6512 -0.0067 0.036 Uiso 1 1 d R . . H4W H 0.2766 0.6495 -0.0645 0.036 Uiso 1 1 d R . . O3W O 0.2791(8) 0.49239(19) 0.0632(4) 0.0532(12) Uani 1 1 d . . . H5W H 0.2830 0.4850 -0.0053 0.080 Uiso 1 1 d R . . H6W H 0.2005 0.4552 0.0647 0.080 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 Sm1 0.01191(14) 0.01346(14) 0.01474(14) 0.00098(7) 0.00647(10) 0.00097(7) C1 0.015(2) 0.0119(19) 0.020(2) -0.0014(15) 0.0106(16) -0.0004(15) C2 0.0131(19) 0.0099(18) 0.0188(19) 0.0008(15) 0.0083(16) -0.0010(15) C3 0.0136(19) 0.0133(19) 0.020(2) 0.0016(15) 0.0095(16) 0.0003(15) C4 0.020(2) 0.024(2) 0.020(2) -0.0043(17) 0.0099(17) -0.0017(18) C5 0.020(2) 0.020(2) 0.022(2) -0.0004(17) 0.0102(18) -0.0031(17) C6 0.035(3) 0.019(2) 0.035(3) -0.0035(19) 0.012(2) -0.007(2) C7 0.030(3) 0.021(2) 0.039(3) 0.009(2) 0.014(2) 0.0102(19) C8 0.018(2) 0.023(2) 0.021(2) 0.0052(17) 0.0091(18) 0.0040(17) C9 0.017(2) 0.024(2) 0.020(2) 0.0099(17) 0.0102(17) 0.0040(17) N1 0.0133(16) 0.0124(16) 0.0151(16) -0.0001(12) 0.0072(13) -0.0010(12) N2 0.0171(17) 0.0174(18) 0.0203(16) 0.0010(14) 0.0104(14) 0.0021(14) N3 0.040(3) 0.020(2) 0.052(3) 0.0016(19) 0.017(2) 0.0040(19) O1 0.0183(15) 0.0270(16) 0.0172(14) 0.0011(12) 0.0097(12) 0.0050(12) O2 0.0165(15) 0.0300(17) 0.0248(15) 0.0034(13) 0.0142(13) 0.0005(12) O3 0.0160(15) 0.0230(16) 0.0255(16) -0.0029(12) 0.0063(13) 0.0025(12) O4 0.0201(17) 0.036(2) 0.0389(19) -0.0091(14) 0.0125(15) -0.0104(13) O5 0.0174(15) 0.0217(16) 0.0331(17) 0.0103(12) 0.0092(13) 0.0014(12) O6 0.0174(16) 0.0332(19) 0.0405(19) 0.0146(14) 0.0128(14) 0.0055(13) O1W 0.0321(18) 0.0225(16) 0.0308(17) -0.0040(13) 0.0184(14) 0.0012(13) O2W 0.0236(16) 0.0244(16) 0.0240(15) 0.0061(13) 0.0113(13) 0.0020(13) O3W 0.081(3) 0.044(2) 0.069(3) -0.039(2) 0.063(2) -0.041(2) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag Sm1 O5 2.427(3) . ? Sm1 O1 2.428(3) . ? Sm1 O3W 2.444(3) . ? Sm1 O2W 2.480(3) . ? Sm1 O2 2.483(3) 1_455 ? Sm1 O3 2.495(3) . ? Sm1 O1W 2.538(3) . ? Sm1 N2 2.547(3) . ? Sm1 N1 2.634(3) . ? C1 O1 1.256(5) . ? C1 O2 1.256(4) . ? C1 C2 1.509(5) . ? C2 N1 1.342(5) . ? C2 C3 1.383(5) 3_766 ? C3 N1 1.335(5) . ? C3 C2 1.383(5) 3_766 ? C3 H3 0.9300 . ? C4 O4 1.230(5) . ? C4 O3 1.272(5) . ? C4 C5 1.515(6) . ? C5 N2 1.335(5) . ? C5 C6 1.388(6) . ? C6 N3 1.332(6) . ? C6 H6 0.9300 . ? C7 N3 1.336(6) . ? C7 C8 1.376(6) . ? C7 H7 0.9300 . ? C8 N2 1.331(5) . ? C8 C9 1.508(6) . ? C9 O6 1.248(5) . ? C9 O5 1.254(5) . ? O2 Sm1 2.483(3) 1_655 ? O1W H1W 0.8594 . ? O1W H2W 0.8588 . ? O2W H3W 0.8627 . ? O2W H4W 0.8601 . ? O3W H5W 0.8575 . ? O3W H6W 0.8563 . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag O5 Sm1 O1 141.46(10) . . ? O5 Sm1 O3W 82.29(13) . . ? O1 Sm1 O3W 71.28(12) . . ? O5 Sm1 O2W 73.11(10) . . ? O1 Sm1 O2W 72.42(9) . . ? O3W Sm1 O2W 72.29(11) . . ? O5 Sm1 O2 79.11(9) . 1_455 ? O1 Sm1 O2 115.32(9) . 1_455 ? O3W Sm1 O2 69.84(10) . 1_455 ? O2W Sm1 O2 135.32(10) . 1_455 ? O5 Sm1 O3 125.49(9) . . ? O1 Sm1 O3 69.94(9) . . ? O3W Sm1 O3 140.33(11) . . ? O2W Sm1 O3 88.32(10) . . ? O2 Sm1 O3 136.32(9) 1_455 . ? O5 Sm1 O1W 85.28(10) . . ? O1 Sm1 O1W 132.97(9) . . ? O3W Sm1 O1W 138.05(10) . . ? O2W Sm1 O1W 140.39(9) . . ? O2 Sm1 O1W 68.51(9) 1_455 . ? O3 Sm1 O1W 77.60(10) . . ? O5 Sm1 N2 63.38(10) . . ? O1 Sm1 N2 119.67(10) . . ? O3W Sm1 N2 135.89(13) . . ? O2W Sm1 N2 71.77(10) . . ? O2 Sm1 N2 124.40(10) 1_455 . ? O3 Sm1 N2 62.15(10) . . ? O1W Sm1 N2 68.89(10) . . ? O5 Sm1 N1 150.56(9) . . ? O1 Sm1 N1 63.45(9) . . ? O3W Sm1 N1 98.44(12) . . ? O2W Sm1 N1 135.38(10) . . ? O2 Sm1 N1 73.70(9) 1_455 . ? O3 Sm1 N1 71.26(9) . . ? O1W Sm1 N1 74.54(9) . . ? N2 Sm1 N1 125.18(10) . . ? O1 C1 O2 126.7(3) . . ? O1 C1 C2 115.9(3) . . ? O2 C1 C2 117.4(3) . . ? N1 C2 C3 121.6(3) . 3_766 ? N1 C2 C1 115.5(3) . . ? C3 C2 C1 122.8(3) 3_766 . ? N1 C3 C2 121.6(3) . 3_766 ? N1 C3 H3 119.2 . . ? C2 C3 H3 119.2 3_766 . ? O4 C4 O3 126.0(4) . . ? O4 C4 C5 119.1(4) . . ? O3 C4 C5 115.0(3) . . ? N2 C5 C6 120.4(4) . . ? N2 C5 C4 114.3(4) . . ? C6 C5 C4 125.3(4) . . ? N3 C6 C5 122.1(4) . . ? N3 C6 H6 118.9 . . ? C5 C6 H6 118.9 . . ? N3 C7 C8 122.6(4) . . ? N3 C7 H7 118.7 . . ? C8 C7 H7 118.7 . . ? N2 C8 C7 120.5(4) . . ? N2 C8 C9 114.7(4) . . ? C7 C8 C9 124.8(4) . . ? O6 C9 O5 125.8(4) . . ? O6 C9 C8 118.2(4) . . ? O5 C9 C8 116.0(4) . . ? C3 N1 C2 116.8(3) . . ? C3 N1 Sm1 127.8(2) . . ? C2 N1 Sm1 115.4(2) . . ? C8 N2 C5 118.2(4) . . ? C8 N2 Sm1 119.3(3) . . ? C5 N2 Sm1 122.2(3) . . ? C6 N3 C7 116.2(4) . . ? C1 O1 Sm1 122.8(2) . . ? C1 O2 Sm1 136.9(3) . 1_655 ? C4 O3 Sm1 126.3(3) . . ? C9 O5 Sm1 126.0(3) . . ? Sm1 O1W H1W 121.4 . . ? Sm1 O1W H2W 115.8 . . ? H1W O1W H2W 98.5 . . ? Sm1 O2W H3W 109.1 . . ? Sm1 O2W H4W 117.1 . . ? H3W O2W H4W 98.4 . . ? Sm1 O3W H5W 124.4 . . ? Sm1 O3W H6W 136.4 . . ? H5W O3W H6W 99.2 . . ? 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 O1 C1 C2 N1 -19.8(5) . . . . ? O2 C1 C2 N1 160.8(3) . . . . ? O1 C1 C2 C3 158.7(4) . . . 3_766 ? O2 C1 C2 C3 -20.7(5) . . . 3_766 ? O4 C4 C5 N2 176.5(4) . . . . ? O3 C4 C5 N2 -3.4(5) . . . . ? O4 C4 C5 C6 -5.4(6) . . . . ? O3 C4 C5 C6 174.7(4) . . . . ? N2 C5 C6 N3 1.3(7) . . . . ? C4 C5 C6 N3 -176.7(4) . . . . ? N3 C7 C8 N2 1.8(7) . . . . ? N3 C7 C8 C9 179.8(4) . . . . ? N2 C8 C9 O6 -179.8(4) . . . . ? C7 C8 C9 O6 2.1(6) . . . . ? N2 C8 C9 O5 -0.5(5) . . . . ? C7 C8 C9 O5 -178.6(4) . . . . ? C2 C3 N1 C2 -0.4(6) 3_766 . . . ? C2 C3 N1 Sm1 178.2(3) 3_766 . . . ? C3 C2 N1 C3 0.4(6) 3_766 . . . ? C1 C2 N1 C3 179.0(3) . . . . ? C3 C2 N1 Sm1 -178.4(3) 3_766 . . . ? C1 C2 N1 Sm1 0.2(4) . . . . ? O5 Sm1 N1 C3 -15.3(4) . . . . ? O1 Sm1 N1 C3 -168.7(3) . . . . ? O3W Sm1 N1 C3 -104.6(3) . . . . ? O2W Sm1 N1 C3 -177.9(3) . . . . ? O2 Sm1 N1 C3 -38.6(3) 1_455 . . . ? O3 Sm1 N1 C3 114.9(3) . . . . ? O1W Sm1 N1 C3 33.1(3) . . . . ? N2 Sm1 N1 C3 82.4(3) . . . . ? O5 Sm1 N1 C2 163.3(2) . . . . ? O1 Sm1 N1 C2 9.9(2) . . . . ? O3W Sm1 N1 C2 74.0(3) . . . . ? O2W Sm1 N1 C2 0.7(3) . . . . ? O2 Sm1 N1 C2 140.1(3) 1_455 . . . ? O3 Sm1 N1 C2 -66.4(3) . . . . ? O1W Sm1 N1 C2 -148.3(3) . . . . ? N2 Sm1 N1 C2 -99.0(3) . . . . ? C7 C8 N2 C5 -0.9(6) . . . . ? C9 C8 N2 C5 -179.1(3) . . . . ? C7 C8 N2 Sm1 172.7(3) . . . . ? C9 C8 N2 Sm1 -5.5(4) . . . . ? C6 C5 N2 C8 -0.6(6) . . . . ? C4 C5 N2 C8 177.6(3) . . . . ? C6 C5 N2 Sm1 -174.0(3) . . . . ? C4 C5 N2 Sm1 4.2(5) . . . . ? O5 Sm1 N2 C8 6.2(3) . . . . ? O1 Sm1 N2 C8 142.3(3) . . . . ? O3W Sm1 N2 C8 49.1(3) . . . . ? O2W Sm1 N2 C8 86.0(3) . . . . ? O2 Sm1 N2 C8 -47.0(3) 1_455 . . . ? O3 Sm1 N2 C8 -176.0(3) . . . . ? O1W Sm1 N2 C8 -89.3(3) . . . . ? N1 Sm1 N2 C8 -140.8(3) . . . . ? O5 Sm1 N2 C5 179.5(3) . . . . ? O1 Sm1 N2 C5 -44.3(3) . . . . ? O3W Sm1 N2 C5 -137.6(3) . . . . ? O2W Sm1 N2 C5 -100.7(3) . . . . ? O2 Sm1 N2 C5 126.3(3) 1_455 . . . ? O3 Sm1 N2 C5 -2.7(3) . . . . ? O1W Sm1 N2 C5 84.1(3) . . . . ? N1 Sm1 N2 C5 32.5(3) . . . . ? C5 C6 N3 C7 -0.4(7) . . . . ? C8 C7 N3 C6 -1.1(7) . . . . ? O2 C1 O1 Sm1 -148.2(3) . . . . ? C2 C1 O1 Sm1 32.5(4) . . . . ? O5 Sm1 O1 C1 177.5(3) . . . . ? O3W Sm1 O1 C1 -133.2(3) . . . . ? O2W Sm1 O1 C1 150.0(3) . . . . ? O2 Sm1 O1 C1 -77.5(3) 1_455 . . . ? O3 Sm1 O1 C1 55.3(3) . . . . ? O1W Sm1 O1 C1 6.0(3) . . . . ? N2 Sm1 O1 C1 94.0(3) . . . . ? N1 Sm1 O1 C1 -23.2(3) . . . . ? O1 C1 O2 Sm1 47.7(6) . . . 1_655 ? C2 C1 O2 Sm1 -133.0(3) . . . 1_655 ? O4 C4 O3 Sm1 -178.7(3) . . . . ? C5 C4 O3 Sm1 1.1(5) . . . . ? O5 Sm1 O3 C4 3.0(4) . . . . ? O1 Sm1 O3 C4 142.7(3) . . . . ? O3W Sm1 O3 C4 130.0(3) . . . . ? O2W Sm1 O3 C4 70.8(3) . . . . ? O2 Sm1 O3 C4 -111.2(3) 1_455 . . . ? O1W Sm1 O3 C4 -71.9(3) . . . . ? N2 Sm1 O3 C4 0.6(3) . . . . ? N1 Sm1 O3 C4 -149.5(3) . . . . ? O6 C9 O5 Sm1 -173.7(3) . . . . ? C8 C9 O5 Sm1 7.0(5) . . . . ? O1 Sm1 O5 C9 -112.1(3) . . . . ? O3W Sm1 O5 C9 -158.5(3) . . . . ? O2W Sm1 O5 C9 -84.7(3) . . . . ? O2 Sm1 O5 C9 130.7(3) 1_455 . . . ? O3 Sm1 O5 C9 -9.5(4) . . . . ? O1W Sm1 O5 C9 61.7(3) . . . . ? N2 Sm1 O5 C9 -7.1(3) . . . . ? N1 Sm1 O5 C9 108.0(3) . . . . ? loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA _geom_hbond_site_symmetry_A O3W H6W O5 0.86 2.34 3.040(4) 139.4 3_565 O3W H5W O1 0.86 1.98 2.817(4) 166.4 3_665 O2W H4W O4 0.86 2.01 2.853(4) 166.1 4_475 O2W H3W O6 0.86 1.85 2.702(4) 167.5 1_655 O1W H2W O4 0.86 2.36 3.049(4) 137.1 1_455 O1W H2W O3 0.86 2.31 3.145(4) 163.5 1_455 O1W H1W O6 0.86 1.98 2.831(4) 171.9 4_676 _diffrn_measured_fraction_theta_max 0.994 _diffrn_reflns_theta_full 25.50 _diffrn_measured_fraction_theta_full 0.994 _refine_diff_density_max 1.989 _refine_diff_density_min -1.242 _refine_diff_density_rms 0.163 # Attachment '- 2-Tb.cif' data_2-Tb _database_code_depnum_ccdc_archive 'CCDC 782474' #TrackingRef '- 2-Tb.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C9 H9 N3 O9 Tb' _chemical_formula_sum 'C9 H9 N3 O9 Tb' _chemical_formula_weight 462.11 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 'P 21/c ' _symmetry_space_group_name_Hall '-P 2ybc ' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y-1/2, z-1/2' _cell_length_a 5.9955(14) _cell_length_b 18.987(4) _cell_length_c 12.101(3) _cell_angle_alpha 90.00 _cell_angle_beta 119.371(9) _cell_angle_gamma 90.00 _cell_volume 1200.5(5) _cell_formula_units_Z 4 _cell_measurement_temperature 298(2) _cell_measurement_reflns_used 3804 _cell_measurement_theta_min 2.21 _cell_measurement_theta_max 28.27 _exptl_crystal_description block _exptl_crystal_colour colorless _exptl_crystal_size_max 0.16 _exptl_crystal_size_mid 0.10 _exptl_crystal_size_min 0.05 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 2.557 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 884 _exptl_absorpt_coefficient_mu 5.951 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.4494 _exptl_absorpt_correction_T_max 0.7551 _exptl_absorpt_process_details 'SADABS, Bruker(2002)' _exptl_special_details ; ? ; _diffrn_ambient_temperature 298(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type ? _diffrn_measurement_method ? _diffrn_detector_area_resol_mean ? _diffrn_reflns_number 6404 _diffrn_reflns_av_R_equivalents 0.0421 _diffrn_reflns_av_sigmaI/netI 0.0439 _diffrn_reflns_limit_h_min -7 _diffrn_reflns_limit_h_max 7 _diffrn_reflns_limit_k_min -23 _diffrn_reflns_limit_k_max 23 _diffrn_reflns_limit_l_min -14 _diffrn_reflns_limit_l_max 12 _diffrn_reflns_theta_min 2.15 _diffrn_reflns_theta_max 25.98 _reflns_number_total 2339 _reflns_number_gt 2106 _reflns_threshold_expression >2sigma(I) _computing_data_collection ? _computing_cell_refinement ? _computing_data_reduction ? _computing_structure_solution 'SHELXS-97 (Sheldrick, 2008)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _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^)+(0.0338P)^2^+0.6224P] 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 2339 _refine_ls_number_parameters 199 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0324 _refine_ls_R_factor_gt 0.0281 _refine_ls_wR_factor_ref 0.0660 _refine_ls_wR_factor_gt 0.0641 _refine_ls_goodness_of_fit_ref 1.031 _refine_ls_restrained_S_all 1.031 _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 0.45599(4) 0.596988(10) 0.194796(18) 0.01307(9) Uani 1 1 d . . . C1 C 1.0063(8) 0.5267(2) 0.2700(4) 0.0154(9) Uani 1 1 d . . . C2 C 1.0075(8) 0.5122(2) 0.3935(4) 0.0141(9) Uani 1 1 d . . . C3 C 0.7934(8) 0.5225(2) 0.5047(4) 0.0148(9) Uani 1 1 d . . . H3 H 0.6526 0.5375 0.5112 0.018 Uiso 1 1 calc R . . C4 C 0.8621(9) 0.7353(2) 0.2845(4) 0.0204(10) Uani 1 1 d . . . C5 C 0.6027(9) 0.7723(2) 0.2133(4) 0.0186(10) Uani 1 1 d . . . C6 C 0.5642(11) 0.8439(3) 0.2026(5) 0.0308(12) Uani 1 1 d . . . H6 H 0.7057 0.8736 0.2374 0.037 Uiso 1 1 calc R . . C7 C 0.1348(10) 0.8267(3) 0.0950(5) 0.0309(12) Uani 1 1 d . . . H7 H -0.0313 0.8443 0.0544 0.037 Uiso 1 1 calc R . . C8 C 0.1689(9) 0.7552(2) 0.1023(4) 0.0202(10) Uani 1 1 d . . . C9 C -0.0420(9) 0.7019(2) 0.0494(4) 0.0204(10) Uani 1 1 d . . . N1 N 0.8008(7) 0.53463(18) 0.3985(3) 0.0147(8) Uani 1 1 d . . . N2 N 0.4041(7) 0.72873(19) 0.1625(3) 0.0170(8) Uani 1 1 d . . . N3 N 0.3293(9) 0.8722(2) 0.1434(5) 0.0379(11) Uani 1 1 d . . . O1 O 0.7907(6) 0.53839(16) 0.1761(3) 0.0180(7) Uani 1 1 d . . . O2 O 1.2184(6) 0.52510(17) 0.2721(3) 0.0205(7) Uani 1 1 d . . . O3 O 0.8478(6) 0.66911(16) 0.2901(3) 0.0231(7) Uani 1 1 d . . . O4 O 1.0564(6) 0.77116(19) 0.3297(3) 0.0308(9) Uani 1 1 d . . . O5 O 0.0268(6) 0.63867(16) 0.0673(3) 0.0218(7) Uani 1 1 d . . . O6 O -0.2681(6) 0.72303(18) -0.0094(3) 0.0294(8) Uani 1 1 d . . . O1W O 0.4382(6) 0.65546(16) 0.3750(3) 0.0242(7) Uani 1 1 d . . . H1W H 0.5156 0.6944 0.4061 0.036 Uiso 1 1 d R . . H2W H 0.2884 0.6675 0.3604 0.036 Uiso 1 1 d R . . O2W O 0.4060(6) 0.62336(17) -0.0133(3) 0.0234(7) Uani 1 1 d . . . H3W H 0.5274 0.6510 -0.0045 0.035 Uiso 1 1 d R . . H4W H 0.2789 0.6493 -0.0623 0.035 Uiso 1 1 d R . . O3W O 0.2780(8) 0.49439(19) 0.0648(4) 0.0425(11) Uani 1 1 d . . . H5W H 0.2818 0.4870 -0.0037 0.064 Uiso 1 1 d R . . H6W H 0.1994 0.4572 0.0663 0.064 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 0.00795(14) 0.01520(13) 0.01458(14) 0.00079(8) 0.00439(10) 0.00096(8) C1 0.015(2) 0.014(2) 0.021(2) -0.0027(18) 0.0115(19) 0.0006(18) C2 0.010(2) 0.013(2) 0.019(2) 0.0009(17) 0.0063(18) -0.0022(18) C3 0.008(2) 0.017(2) 0.019(2) 0.0020(17) 0.0072(18) 0.0008(18) C4 0.018(3) 0.026(2) 0.018(2) -0.0045(19) 0.008(2) -0.004(2) C5 0.013(2) 0.025(2) 0.017(2) -0.0006(19) 0.0063(19) -0.0032(19) C6 0.029(3) 0.021(3) 0.036(3) -0.003(2) 0.011(2) -0.007(2) C7 0.025(3) 0.026(3) 0.036(3) 0.007(2) 0.010(2) 0.009(2) C8 0.016(3) 0.021(2) 0.021(2) 0.0072(19) 0.007(2) 0.006(2) C9 0.015(2) 0.029(3) 0.018(2) 0.009(2) 0.009(2) 0.003(2) N1 0.0111(19) 0.0152(18) 0.0199(19) 0.0007(15) 0.0092(16) -0.0003(15) N2 0.014(2) 0.017(2) 0.0180(18) 0.0005(16) 0.0066(16) 0.0007(16) N3 0.037(3) 0.016(2) 0.053(3) 0.003(2) 0.016(2) 0.006(2) O1 0.0120(16) 0.0266(17) 0.0135(15) 0.0007(13) 0.0048(13) 0.0041(14) O2 0.0111(17) 0.0297(18) 0.0230(16) 0.0029(14) 0.0102(14) -0.0011(14) O3 0.0113(17) 0.0227(17) 0.0301(18) -0.0016(14) 0.0060(14) 0.0007(14) O4 0.018(2) 0.039(2) 0.036(2) -0.0086(16) 0.0127(17) -0.0110(16) O5 0.0095(17) 0.0183(17) 0.0303(18) 0.0071(14) 0.0042(14) 0.0019(13) O6 0.0134(19) 0.036(2) 0.036(2) 0.0148(16) 0.0097(16) 0.0072(15) O1W 0.0191(19) 0.0254(18) 0.0284(19) -0.0047(14) 0.0118(15) 0.0006(15) O2W 0.0185(18) 0.0259(17) 0.0242(17) 0.0049(15) 0.0094(15) 0.0002(15) O3W 0.060(3) 0.037(2) 0.053(2) -0.0280(19) 0.045(2) -0.030(2) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag Tb1 O5 2.394(3) . ? Tb1 O1 2.400(3) . ? Tb1 O3W 2.401(3) . ? Tb1 O2W 2.438(3) . ? Tb1 O3 2.463(3) . ? Tb1 O2 2.465(3) 1_455 ? Tb1 O1W 2.496(3) . ? Tb1 N2 2.527(4) . ? Tb1 N1 2.599(4) . ? C1 O1 1.253(5) . ? C1 O2 1.259(5) . ? C1 C2 1.516(6) . ? C2 N1 1.339(5) . ? C2 C3 1.391(6) 3_766 ? C3 N1 1.329(5) . ? C3 C2 1.391(6) 3_766 ? C3 H3 0.9300 . ? C4 O4 1.223(5) . ? C4 O3 1.263(5) . ? C4 C5 1.530(7) . ? C5 N2 1.327(6) . ? C5 C6 1.374(6) . ? C6 N3 1.341(7) . ? C6 H6 0.9300 . ? C7 N3 1.334(7) . ? C7 C8 1.370(6) . ? C7 H7 0.9300 . ? C8 N2 1.328(6) . ? C8 C9 1.496(7) . ? C9 O6 1.249(6) . ? C9 O5 1.254(5) . ? O2 Tb1 2.465(3) 1_655 ? O1W H1W 0.8549 . ? O1W H2W 0.8572 . ? O2W H3W 0.8605 . ? O2W H4W 0.8548 . ? O3W H5W 0.8522 . ? O3W H6W 0.8534 . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag O5 Tb1 O1 140.93(10) . . ? O5 Tb1 O3W 81.61(13) . . ? O1 Tb1 O3W 71.67(12) . . ? O5 Tb1 O2W 73.59(11) . . ? O1 Tb1 O2W 71.51(10) . . ? O3W Tb1 O2W 72.52(12) . . ? O5 Tb1 O3 126.49(10) . . ? O1 Tb1 O3 69.65(10) . . ? O3W Tb1 O3 140.66(12) . . ? O2W Tb1 O3 88.58(11) . . ? O5 Tb1 O2 77.83(10) . 1_455 ? O1 Tb1 O2 116.39(11) . 1_455 ? O3W Tb1 O2 69.23(11) . 1_455 ? O2W Tb1 O2 134.81(11) . 1_455 ? O3 Tb1 O2 136.58(11) . 1_455 ? O5 Tb1 O1W 85.59(11) . . ? O1 Tb1 O1W 133.19(10) . . ? O3W Tb1 O1W 137.56(11) . . ? O2W Tb1 O1W 140.82(10) . . ? O3 Tb1 O1W 77.49(11) . . ? O2 Tb1 O1W 68.55(10) 1_455 . ? O5 Tb1 N2 63.98(11) . . ? O1 Tb1 N2 119.30(11) . . ? O3W Tb1 N2 136.08(13) . . ? O2W Tb1 N2 72.14(11) . . ? O3 Tb1 N2 62.54(11) . . ? O2 Tb1 N2 123.83(11) 1_455 . ? O1W Tb1 N2 68.92(11) . . ? O5 Tb1 N1 149.93(10) . . ? O1 Tb1 N1 64.21(10) . . ? O3W Tb1 N1 98.23(13) . . ? O2W Tb1 N1 135.31(11) . . ? O3 Tb1 N1 71.15(11) . . ? O2 Tb1 N1 74.15(11) 1_455 . ? O1W Tb1 N1 74.27(11) . . ? N2 Tb1 N1 125.31(11) . . ? O1 C1 O2 127.3(4) . . ? O1 C1 C2 115.4(4) . . ? O2 C1 C2 117.3(4) . . ? N1 C2 C3 121.5(4) . 3_766 ? N1 C2 C1 115.4(4) . . ? C3 C2 C1 123.1(4) 3_766 . ? N1 C3 C2 121.2(4) . 3_766 ? N1 C3 H3 119.4 . . ? C2 C3 H3 119.4 3_766 . ? O4 C4 O3 127.2(5) . . ? O4 C4 C5 118.6(4) . . ? O3 C4 C5 114.2(4) . . ? N2 C5 C6 120.1(4) . . ? N2 C5 C4 114.0(4) . . ? C6 C5 C4 125.8(4) . . ? N3 C6 C5 122.1(5) . . ? N3 C6 H6 118.9 . . ? C5 C6 H6 118.9 . . ? N3 C7 C8 122.9(5) . . ? N3 C7 H7 118.5 . . ? C8 C7 H7 118.5 . . ? N2 C8 C7 119.7(5) . . ? N2 C8 C9 115.2(4) . . ? C7 C8 C9 125.1(4) . . ? O6 C9 O5 125.4(5) . . ? O6 C9 C8 118.7(4) . . ? O5 C9 C8 115.9(4) . . ? C3 N1 C2 117.3(4) . . ? C3 N1 Tb1 127.5(3) . . ? C2 N1 Tb1 115.2(3) . . ? C8 N2 C5 119.2(4) . . ? C8 N2 Tb1 118.4(3) . . ? C5 N2 Tb1 122.1(3) . . ? C7 N3 C6 115.9(4) . . ? C1 O1 Tb1 122.4(3) . . ? C1 O2 Tb1 138.1(3) . 1_655 ? C4 O3 Tb1 127.0(3) . . ? C9 O5 Tb1 125.9(3) . . ? Tb1 O1W H1W 121.4 . . ? Tb1 O1W H2W 115.3 . . ? H1W O1W H2W 98.5 . . ? Tb1 O2W H3W 109.2 . . ? Tb1 O2W H4W 116.7 . . ? H3W O2W H4W 98.4 . . ? Tb1 O3W H5W 123.8 . . ? Tb1 O3W H6W 136.9 . . ? H5W O3W H6W 99.4 . . ? loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA _geom_hbond_site_symmetry_A O3W H6W O5 0.85 2.37 3.068(5) 139.3 3_565 O3W H5W O1 0.85 1.97 2.807(5) 166.6 3_665 O2W H4W O4 0.85 2.02 2.847(5) 164.3 4_475 O2W H3W O6 0.86 1.86 2.704(5) 167.6 1_655 O1W H2W O4 0.86 2.33 3.022(5) 137.7 1_455 O1W H2W O3 0.86 2.34 3.176(4) 163.5 1_455 O1W H1W O6 0.85 1.97 2.822(5) 172.9 4_676 _diffrn_measured_fraction_theta_max 0.992 _diffrn_reflns_theta_full 25.98 _diffrn_measured_fraction_theta_full 0.992 _refine_diff_density_max 1.272 _refine_diff_density_min -1.255 _refine_diff_density_rms 0.175