# Electronic Supplementary Material for CrystEngComm # This journal is (c) The Royal Society of Chemistry 2008 data_global _journal_name_full CrystEngComm _journal_coden_Cambridge 1350 _journal_volume ? _journal_page_first ? _journal_year ? _publ_contact_author_name 'Paul Kruger' _publ_contact_author_email PAUL.KRUGER@CANTERBURY.AC.NZ _publ_section_title ; Synthesis and structural characterisation of lanthanide coordination polymers featuring 4,4',6,6'-tetra-carboxy-2,2'-bipyridine and rare network topology ; loop_ _publ_author_name 'Paul Kruger' 'Stuart Batten' 'Sandrine Goetz' 'Niamh R Kelly' # Attachment 'B801985A__revised.cif' data_1 _database_code_depnum_ccdc_archive 'CCDC 677289' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common 7 _chemical_melting_point ? _chemical_formula_moiety 'C14 H11 La N2 O11, H2 O' _chemical_formula_sum 'C14 H13 La N2 O12' _chemical_formula_weight 540.17 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' La La -0.2871 2.4523 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting triclinic _symmetry_space_group_name_H-M P-1 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 6.9628(3) _cell_length_b 11.0010(3) _cell_length_c 11.5319(5) _cell_angle_alpha 79.8560(10) _cell_angle_beta 73.862(2) _cell_angle_gamma 76.865(2) _cell_volume 820.27(5) _cell_formula_units_Z 2 _cell_measurement_temperature 153(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description block _exptl_crystal_colour red _exptl_crystal_size_max 0.09 _exptl_crystal_size_mid 0.07 _exptl_crystal_size_min 0.04 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 2.187 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 528 _exptl_absorpt_coefficient_mu 2.682 _exptl_absorpt_correction_type empirical _exptl_absorpt_correction_T_min 0.7814 _exptl_absorpt_correction_T_max 1.000 _exptl_absorpt_process_details TWINABS _exptl_special_details ; ? ; _diffrn_ambient_temperature 153(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Bruker SMART APEX CCD' _diffrn_measurement_method 'omega scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 4505 _diffrn_reflns_av_R_equivalents 0.0000 _diffrn_reflns_av_sigmaI/netI 0.0363 _diffrn_reflns_limit_h_min -8 _diffrn_reflns_limit_h_max 9 _diffrn_reflns_limit_k_min -14 _diffrn_reflns_limit_k_max 15 _diffrn_reflns_limit_l_min 0 _diffrn_reflns_limit_l_max 16 _diffrn_reflns_theta_min 1.85 _diffrn_reflns_theta_max 30.49 _reflns_number_total 4505 _reflns_number_gt 4326 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SMART' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'SHELXTL version 5.1 (Sheldrick, 1998)' _computing_structure_refinement 'SHELXTL version 5.1 (Sheldrick, 1998)' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0328P)^2^+0.1836P] 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 mixed _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 4505 _refine_ls_number_parameters 290 _refine_ls_number_restraints 40 _refine_ls_R_factor_all 0.0241 _refine_ls_R_factor_gt 0.0228 _refine_ls_wR_factor_ref 0.0612 _refine_ls_wR_factor_gt 0.0606 _refine_ls_goodness_of_fit_ref 1.059 _refine_ls_restrained_S_all 1.056 _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 La1 La 0.666434(16) 0.467805(9) 0.243269(9) 0.01043(5) Uani 1 1 d . . . N1 N 0.8962(3) 0.26612(16) 0.13068(16) 0.0122(3) Uani 1 1 d . . . C1 C 0.9839(3) 0.28824(19) 0.01134(19) 0.0120(4) Uani 1 1 d . . . C2 C 1.1260(3) 0.1984(2) -0.05363(19) 0.0135(4) Uani 1 1 d . . . H2A H 1.1869 0.2175 -0.1376 0.016 Uiso 1 1 calc R . . C3 C 1.1771(3) 0.0796(2) 0.0075(2) 0.0131(4) Uani 1 1 d . . . C4 C 1.0821(3) 0.0543(2) 0.12961(19) 0.0133(4) Uani 1 1 d . . . H4A H 1.1125 -0.0268 0.1725 0.016 Uiso 1 1 calc R . . C5 C 0.9409(3) 0.15048(19) 0.18826(19) 0.0116(4) Uani 1 1 d . . . C6 C 0.8276(3) 0.13036(19) 0.31751(19) 0.0112(4) Uani 1 1 d . . . C7 C 0.8481(3) 0.01382(19) 0.38811(19) 0.0126(4) Uani 1 1 d . . . H7A H 0.9335 -0.0578 0.3531 0.015 Uiso 1 1 calc R . . C8 C 0.7430(3) 0.00270(19) 0.51015(19) 0.0117(4) Uani 1 1 d . . . C9 C 0.6207(3) 0.10987(19) 0.55777(19) 0.0129(4) Uani 1 1 d . . . H9A H 0.5523 0.1070 0.6416 0.016 Uiso 1 1 calc R . . C10 C 0.6006(3) 0.22111(19) 0.48028(19) 0.0116(4) Uani 1 1 d . . . N2 N 0.7001(3) 0.23236(16) 0.36277(16) 0.0111(3) Uani 1 1 d . . . C11 C 0.4604(3) 0.33967(19) 0.52408(19) 0.0128(4) Uani 1 1 d . . . O1 O 0.4162(2) 0.42620(14) 0.44211(14) 0.0140(3) Uani 1 1 d . . . O2 O 0.3989(2) 0.34346(14) 0.63651(14) 0.0159(3) Uani 1 1 d . . . C12 C 0.7670(3) -0.12561(19) 0.58599(19) 0.0128(4) Uani 1 1 d . . . O3 O 0.6734(2) -0.13562(15) 0.69648(14) 0.0172(3) Uani 1 1 d . . . O4 O 0.8810(3) -0.21469(15) 0.53235(15) 0.0186(3) Uani 1 1 d . . . C13 C 1.3300(3) -0.0224(2) -0.05696(19) 0.0138(4) Uani 1 1 d . . . O5 O 1.3814(3) -0.12481(16) -0.00506(16) 0.0231(4) Uani 1 1 d . . . O6 O 1.3979(3) 0.01404(16) -0.17259(16) 0.0226(4) Uani 1 1 d . . . H6 H 1.485(6) -0.043(4) -0.205(4) 0.048(11) Uiso 1 1 d . . . C14 C 0.9165(3) 0.41794(19) -0.04957(19) 0.0123(4) Uani 1 1 d . . . O7 O 1.0153(2) 0.44672(14) -0.15695(14) 0.0144(3) Uani 1 1 d . . . O8 O 0.7668(2) 0.48816(14) 0.00914(14) 0.0145(3) Uani 1 1 d . . . O1W O 0.4150(3) 0.37054(16) 0.18727(16) 0.0199(3) Uani 1 1 d D . . H1W1 H 0.393(5) 0.2984(16) 0.210(3) 0.030 Uiso 1 1 d D . . H2W1 H 0.354(4) 0.400(3) 0.133(2) 0.030 Uiso 1 1 d D . . O2W O 0.4341(3) 0.65079(16) 0.15858(17) 0.0221(4) Uani 1 1 d D . . H1W2 H 0.457(5) 0.701(3) 0.0955(19) 0.033 Uiso 1 1 d D . . H2W2 H 0.325(3) 0.683(3) 0.203(2) 0.033 Uiso 1 1 d D . . O3W O 0.8887(3) 0.43355(16) 0.39586(15) 0.0180(3) Uani 1 1 d D . . H1W3 H 0.975(4) 0.372(2) 0.412(3) 0.027 Uiso 1 1 d D . . H2W3 H 0.831(4) 0.464(3) 0.4607(17) 0.027 Uiso 1 1 d D . . O4W O 0.0695(3) 0.7073(2) 0.3083(2) 0.0378(5) Uani 1 1 d D . . H1W4 H 0.009(6) 0.653(3) 0.299(4) 0.057 Uiso 1 1 d D . . H2W4 H 0.006(5) 0.733(4) 0.376(2) 0.057 Uiso 1 1 d D . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 La1 0.01211(7) 0.00925(7) 0.00693(7) -0.00008(4) 0.00078(5) -0.00061(4) N1 0.0139(8) 0.0115(8) 0.0090(8) -0.0008(6) 0.0005(6) -0.0023(6) C1 0.0137(9) 0.0124(9) 0.0091(9) -0.0014(7) -0.0010(7) -0.0029(7) C2 0.0150(9) 0.0136(9) 0.0097(9) -0.0025(7) 0.0010(8) -0.0026(7) C3 0.0128(9) 0.0137(9) 0.0113(10) -0.0032(7) 0.0002(8) -0.0026(7) C4 0.0140(9) 0.0140(9) 0.0095(9) -0.0013(7) -0.0004(8) -0.0011(7) C5 0.0124(9) 0.0120(9) 0.0090(9) -0.0007(7) -0.0005(7) -0.0024(7) C6 0.0117(9) 0.0116(9) 0.0088(9) -0.0019(7) -0.0005(7) -0.0015(7) C7 0.0128(9) 0.0117(9) 0.0111(10) -0.0016(7) -0.0008(7) -0.0002(7) C8 0.0137(9) 0.0105(9) 0.0104(9) -0.0001(7) -0.0026(7) -0.0024(7) C9 0.0140(9) 0.0127(9) 0.0095(9) -0.0007(7) 0.0003(7) -0.0020(7) C10 0.0127(9) 0.0108(9) 0.0092(9) -0.0006(7) -0.0001(7) -0.0016(7) N2 0.0113(8) 0.0117(8) 0.0079(8) -0.0018(6) 0.0007(6) -0.0005(6) C11 0.0132(9) 0.0112(9) 0.0115(10) -0.0013(7) 0.0009(7) -0.0026(7) O1 0.0158(7) 0.0120(7) 0.0104(7) -0.0003(5) 0.0009(6) -0.0007(5) O2 0.0223(8) 0.0122(7) 0.0086(7) -0.0012(5) 0.0017(6) -0.0006(6) C12 0.0133(9) 0.0122(9) 0.0121(10) 0.0000(7) -0.0030(8) -0.0021(7) O3 0.0212(8) 0.0140(7) 0.0108(7) 0.0001(6) 0.0024(6) -0.0011(6) O4 0.0244(8) 0.0122(7) 0.0132(8) -0.0020(6) 0.0004(6) 0.0027(6) C13 0.0130(9) 0.0144(9) 0.0117(10) -0.0033(7) 0.0010(8) -0.0016(7) O5 0.0284(9) 0.0165(8) 0.0158(8) 0.0000(6) 0.0015(7) 0.0031(7) O6 0.0284(9) 0.0167(8) 0.0123(8) -0.0022(6) 0.0057(7) 0.0036(7) C14 0.0152(9) 0.0130(9) 0.0089(9) -0.0011(7) -0.0019(7) -0.0045(7) O7 0.0162(7) 0.0161(7) 0.0082(7) 0.0005(6) 0.0008(6) -0.0040(6) O8 0.0169(7) 0.0139(7) 0.0097(7) -0.0006(5) -0.0010(6) -0.0002(6) O1W 0.0222(8) 0.0173(8) 0.0219(9) 0.0052(7) -0.0103(7) -0.0072(7) O2W 0.0242(9) 0.0166(8) 0.0191(9) 0.0018(6) -0.0042(7) 0.0046(7) O3W 0.0200(8) 0.0174(8) 0.0132(8) -0.0015(6) -0.0038(6) 0.0028(6) O4W 0.0315(11) 0.0554(14) 0.0291(11) -0.0260(10) 0.0042(9) -0.0121(10) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag La1 O7 2.4855(15) 2_765 ? La1 O1 2.5050(15) . ? La1 O2W 2.5156(17) . ? La1 O1W 2.5200(16) . ? La1 O8 2.5763(15) . ? La1 O3W 2.5782(17) . ? La1 O2 2.5834(15) 2_666 ? La1 N2 2.7036(17) . ? La1 N1 2.7231(17) . ? N1 C5 1.339(3) . ? N1 C1 1.345(3) . ? C1 C2 1.386(3) . ? C1 C14 1.509(3) . ? C2 C3 1.391(3) . ? C2 H2A 0.9500 . ? C3 C4 1.388(3) . ? C3 C13 1.501(3) . ? C4 C5 1.398(3) . ? C4 H4A 0.9500 . ? C5 C6 1.484(3) . ? C6 N2 1.347(3) . ? C6 C7 1.393(3) . ? C7 C8 1.393(3) . ? C7 H7A 0.9500 . ? C8 C9 1.389(3) . ? C8 C12 1.525(3) . ? C9 C10 1.386(3) . ? C9 H9A 0.9500 . ? C10 N2 1.338(3) . ? C10 C11 1.513(3) . ? C11 O2 1.252(3) . ? C11 O1 1.267(3) . ? O2 La1 2.5834(15) 2_666 ? C12 O4 1.249(3) . ? C12 O3 1.258(3) . ? C13 O5 1.206(3) . ? C13 O6 1.307(3) . ? O6 H6 0.83(4) . ? C14 O8 1.252(3) . ? C14 O7 1.263(2) . ? O7 La1 2.4855(15) 2_765 ? O1W H1W1 0.827(12) . ? O1W H2W1 0.827(12) . ? O2W H1W2 0.831(12) . ? O2W H2W2 0.835(12) . ? O3W H1W3 0.831(12) . ? O3W H2W3 0.835(12) . ? O4W H1W4 0.846(12) . ? O4W H2W4 0.845(12) . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag O7 La1 O1 140.76(5) 2_765 . ? O7 La1 O2W 96.62(5) 2_765 . ? O1 La1 O2W 95.80(5) . . ? O7 La1 O1W 142.80(5) 2_765 . ? O1 La1 O1W 76.42(5) . . ? O2W La1 O1W 75.18(6) . . ? O7 La1 O8 68.32(5) 2_765 . ? O1 La1 O8 150.40(5) . . ? O2W La1 O8 69.94(5) . . ? O1W La1 O8 74.88(5) . . ? O7 La1 O3W 67.26(5) 2_765 . ? O1 La1 O3W 78.03(5) . . ? O2W La1 O3W 135.88(6) . . ? O1W La1 O3W 141.59(5) . . ? O8 La1 O3W 130.41(5) . . ? O7 La1 O2 77.79(5) 2_765 2_666 ? O1 La1 O2 71.89(5) . 2_666 ? O2W La1 O2 69.98(6) . 2_666 ? O1W La1 O2 129.33(6) . 2_666 ? O8 La1 O2 122.86(5) . 2_666 ? O3W La1 O2 66.58(5) . 2_666 ? O7 La1 N2 117.23(5) 2_765 . ? O1 La1 N2 61.20(5) . . ? O2W La1 N2 145.86(6) . . ? O1W La1 N2 74.97(5) . . ? O8 La1 N2 116.97(5) . . ? O3W La1 N2 67.69(5) . . ? O2 La1 N2 119.20(5) 2_666 . ? O7 La1 N1 82.29(5) 2_765 . ? O1 La1 N1 117.79(5) . . ? O2W La1 N1 127.48(6) . . ? O1W La1 N1 75.25(6) . . ? O8 La1 N1 60.95(5) . . ? O3W La1 N1 92.18(5) . . ? O2 La1 N1 155.20(5) 2_666 . ? N2 La1 N1 58.42(5) . . ? C5 N1 C1 118.60(18) . . ? C5 N1 La1 124.27(13) . . ? C1 N1 La1 116.86(13) . . ? N1 C1 C2 122.96(19) . . ? N1 C1 C14 115.82(18) . . ? C2 C1 C14 121.21(19) . . ? C1 C2 C3 118.22(19) . . ? C1 C2 H2A 120.9 . . ? C3 C2 H2A 120.9 . . ? C4 C3 C2 119.32(19) . . ? C4 C3 C13 119.48(19) . . ? C2 C3 C13 121.19(19) . . ? C3 C4 C5 118.71(19) . . ? C3 C4 H4A 120.6 . . ? C5 C4 H4A 120.6 . . ? N1 C5 C4 122.10(19) . . ? N1 C5 C6 115.69(17) . . ? C4 C5 C6 122.19(18) . . ? N2 C6 C7 121.57(19) . . ? N2 C6 C5 115.64(17) . . ? C7 C6 C5 122.78(18) . . ? C8 C7 C6 119.74(19) . . ? C8 C7 H7A 120.1 . . ? C6 C7 H7A 120.1 . . ? C9 C8 C7 118.24(19) . . ? C9 C8 C12 122.74(19) . . ? C7 C8 C12 119.02(18) . . ? C10 C9 C8 118.55(19) . . ? C10 C9 H9A 120.7 . . ? C8 C9 H9A 120.7 . . ? N2 C10 C9 123.47(19) . . ? N2 C10 C11 115.05(17) . . ? C9 C10 C11 121.47(18) . . ? C10 N2 C6 118.26(17) . . ? C10 N2 La1 116.28(13) . . ? C6 N2 La1 124.91(13) . . ? O2 C11 O1 126.2(2) . . ? O2 C11 C10 117.70(18) . . ? O1 C11 C10 116.09(18) . . ? C11 O1 La1 122.16(13) . . ? C11 O2 La1 128.81(13) . 2_666 ? O4 C12 O3 124.4(2) . . ? O4 C12 C8 116.52(18) . . ? O3 C12 C8 119.10(18) . . ? O5 C13 O6 125.5(2) . . ? O5 C13 C3 122.3(2) . . ? O6 C13 C3 112.13(18) . . ? C13 O6 H6 110(3) . . ? O8 C14 O7 125.0(2) . . ? O8 C14 C1 117.95(18) . . ? O7 C14 C1 117.01(18) . . ? C14 O7 La1 133.18(14) . 2_765 ? C14 O8 La1 122.66(13) . . ? La1 O1W H1W1 127(2) . . ? La1 O1W H2W1 126(2) . . ? H1W1 O1W H2W1 107(3) . . ? La1 O2W H1W2 131(2) . . ? La1 O2W H2W2 121(2) . . ? H1W2 O2W H2W2 107(3) . . ? La1 O3W H1W3 130(2) . . ? La1 O3W H2W3 115(2) . . ? H1W3 O3W H2W3 107(3) . . ? H1W4 O4W H2W4 107(3) . . ? 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 O7 La1 N1 C5 119.38(17) 2_765 . . . ? O1 La1 N1 C5 -24.93(18) . . . . ? O2W La1 N1 C5 -148.17(15) . . . . ? O1W La1 N1 C5 -90.53(17) . . . . ? O8 La1 N1 C5 -171.19(18) . . . . ? O3W La1 N1 C5 52.68(16) . . . . ? O2 La1 N1 C5 82.7(2) 2_666 . . . ? N2 La1 N1 C5 -9.32(15) . . . . ? O7 La1 N1 C1 -54.51(15) 2_765 . . . ? O1 La1 N1 C1 161.18(14) . . . . ? O2W La1 N1 C1 37.94(17) . . . . ? O1W La1 N1 C1 95.58(15) . . . . ? O8 La1 N1 C1 14.92(13) . . . . ? O3W La1 N1 C1 -121.21(15) . . . . ? O2 La1 N1 C1 -91.20(18) 2_666 . . . ? N2 La1 N1 C1 176.78(17) . . . . ? C5 N1 C1 C2 -3.2(3) . . . . ? La1 N1 C1 C2 171.08(16) . . . . ? C5 N1 C1 C14 176.14(18) . . . . ? La1 N1 C1 C14 -9.6(2) . . . . ? N1 C1 C2 C3 1.1(3) . . . . ? C14 C1 C2 C3 -178.21(19) . . . . ? C1 C2 C3 C4 1.3(3) . . . . ? C1 C2 C3 C13 -179.92(19) . . . . ? C2 C3 C4 C5 -1.5(3) . . . . ? C13 C3 C4 C5 179.72(19) . . . . ? C1 N1 C5 C4 3.0(3) . . . . ? La1 N1 C5 C4 -170.84(15) . . . . ? C1 N1 C5 C6 -175.78(18) . . . . ? La1 N1 C5 C6 10.4(2) . . . . ? C3 C4 C5 N1 -0.7(3) . . . . ? C3 C4 C5 C6 177.97(19) . . . . ? N1 C5 C6 N2 -2.8(3) . . . . ? C4 C5 C6 N2 178.43(19) . . . . ? N1 C5 C6 C7 176.4(2) . . . . ? C4 C5 C6 C7 -2.4(3) . . . . ? N2 C6 C7 C8 -3.3(3) . . . . ? C5 C6 C7 C8 177.56(19) . . . . ? C6 C7 C8 C9 -0.4(3) . . . . ? C6 C7 C8 C12 179.91(19) . . . . ? C7 C8 C9 C10 3.4(3) . . . . ? C12 C8 C9 C10 -176.90(19) . . . . ? C8 C9 C10 N2 -3.1(3) . . . . ? C8 C9 C10 C11 176.35(19) . . . . ? C9 C10 N2 C6 -0.4(3) . . . . ? C11 C10 N2 C6 -179.93(18) . . . . ? C9 C10 N2 La1 -172.33(16) . . . . ? C11 C10 N2 La1 8.2(2) . . . . ? C7 C6 N2 C10 3.6(3) . . . . ? C5 C6 N2 C10 -177.14(18) . . . . ? C7 C6 N2 La1 174.80(15) . . . . ? C5 C6 N2 La1 -6.0(2) . . . . ? O7 La1 N2 C10 118.51(14) 2_765 . . . ? O1 La1 N2 C10 -16.82(14) . . . . ? O2W La1 N2 C10 -69.58(18) . . . . ? O1W La1 N2 C10 -99.36(15) . . . . ? O8 La1 N2 C10 -163.28(14) . . . . ? O3W La1 N2 C10 71.45(15) . . . . ? O2 La1 N2 C10 27.63(16) 2_666 . . . ? N1 La1 N2 C10 178.94(17) . . . . ? O7 La1 N2 C6 -52.81(17) 2_765 . . . ? O1 La1 N2 C6 171.86(18) . . . . ? O2W La1 N2 C6 119.11(16) . . . . ? O1W La1 N2 C6 89.32(16) . . . . ? O8 La1 N2 C6 25.40(18) . . . . ? O3W La1 N2 C6 -99.87(17) . . . . ? O2 La1 N2 C6 -143.68(15) 2_666 . . . ? N1 La1 N2 C6 7.62(15) . . . . ? N2 C10 C11 O2 -164.48(19) . . . . ? C9 C10 C11 O2 16.0(3) . . . . ? N2 C10 C11 O1 15.6(3) . . . . ? C9 C10 C11 O1 -163.9(2) . . . . ? O2 C11 O1 La1 144.89(18) . . . . ? C10 C11 O1 La1 -35.2(2) . . . . ? O7 La1 O1 C11 -70.92(18) 2_765 . . . ? O2W La1 O1 C11 -178.84(16) . . . . ? O1W La1 O1 C11 107.97(16) . . . . ? O8 La1 O1 C11 122.43(16) . . . . ? O3W La1 O1 C11 -43.10(15) . . . . ? O2 La1 O1 C11 -112.12(16) 2_666 . . . ? N2 La1 O1 C11 27.85(15) . . . . ? N1 La1 O1 C11 43.01(17) . . . . ? O1 C11 O2 La1 -36.1(3) . . . 2_666 ? C10 C11 O2 La1 144.00(15) . . . 2_666 ? C9 C8 C12 O4 179.8(2) . . . . ? C7 C8 C12 O4 -0.5(3) . . . . ? C9 C8 C12 O3 -0.3(3) . . . . ? C7 C8 C12 O3 179.44(19) . . . . ? C4 C3 C13 O5 -3.6(3) . . . . ? C2 C3 C13 O5 177.6(2) . . . . ? C4 C3 C13 O6 176.7(2) . . . . ? C2 C3 C13 O6 -2.1(3) . . . . ? N1 C1 C14 O8 -9.8(3) . . . . ? C2 C1 C14 O8 169.51(19) . . . . ? N1 C1 C14 O7 170.82(18) . . . . ? C2 C1 C14 O7 -9.9(3) . . . . ? O8 C14 O7 La1 95.8(2) . . . 2_765 ? C1 C14 O7 La1 -84.9(2) . . . 2_765 ? O7 C14 O8 La1 -154.05(16) . . . . ? C1 C14 O8 La1 26.6(2) . . . . ? O7 La1 O8 C14 71.09(15) 2_765 . . . ? O1 La1 O8 C14 -117.95(16) . . . . ? O2W La1 O8 C14 177.19(17) . . . . ? O1W La1 O8 C14 -103.38(16) . . . . ? O3W La1 O8 C14 43.33(17) . . . . ? O2 La1 O8 C14 129.24(15) 2_666 . . . ? N2 La1 O8 C14 -39.41(17) . . . . ? N1 La1 O8 C14 -22.10(15) . . . . ? 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 O6 H6 O3 0.83(4) 1.74(4) 2.550(2) 166(4) 1_654 O1W H1W1 O3 0.827(12) 1.998(14) 2.811(2) 167(3) 2_656 O1W H2W1 O8 0.827(12) 2.123(13) 2.934(2) 167(3) 2_665 O2W H1W2 O5 0.831(12) 2.10(2) 2.850(2) 150(3) 1_465 O2W H2W2 O4W 0.835(12) 1.842(15) 2.652(3) 163(3) . O3W H1W3 O4 0.831(12) 1.892(14) 2.709(2) 167(3) 2_756 O3W H2W3 O1 0.835(12) 2.033(18) 2.775(2) 148(3) 2_666 O4W H1W4 O7 0.846(12) 2.18(3) 2.887(3) 141(3) 2_665 O4W H2W4 O4 0.845(12) 1.899(13) 2.742(3) 176(4) 1_465 _diffrn_measured_fraction_theta_max 0.902 _diffrn_reflns_theta_full 30.49 _diffrn_measured_fraction_theta_full 0.902 _refine_diff_density_max 1.509 _refine_diff_density_min -0.709 _refine_diff_density_rms 0.121 ####END data_2 _database_code_depnum_ccdc_archive 'CCDC 677290' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common 8 _chemical_melting_point ? _chemical_formula_moiety 'C14 H9 La N2 O10' _chemical_formula_sum 'C14 H9 La N2 O10' _chemical_formula_weight 504.14 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' La La -0.2871 2.4523 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Triclinic _symmetry_space_group_name_H-M P-1 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 7.2471(5) _cell_length_b 9.9563(6) _cell_length_c 11.0922(7) _cell_angle_alpha 71.4320(10) _cell_angle_beta 75.0060(10) _cell_angle_gamma 78.6650(10) _cell_volume 727.14(8) _cell_formula_units_Z 2 _cell_measurement_temperature 153(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description block _exptl_crystal_colour colourless _exptl_crystal_size_max 0.06 _exptl_crystal_size_mid 0.05 _exptl_crystal_size_min 0.03 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 2.303 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 488 _exptl_absorpt_coefficient_mu 3.007 _exptl_absorpt_correction_type empirical _exptl_absorpt_correction_T_min 0.7375 _exptl_absorpt_correction_T_max 1.000 _exptl_absorpt_process_details SADABS _exptl_special_details ; ? ; _diffrn_ambient_temperature 153(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Bruker SMART APEX CCD' _diffrn_measurement_method 'omega scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 5729 _diffrn_reflns_av_R_equivalents 0.0225 _diffrn_reflns_av_sigmaI/netI 0.0321 _diffrn_reflns_limit_h_min -8 _diffrn_reflns_limit_h_max 8 _diffrn_reflns_limit_k_min -11 _diffrn_reflns_limit_k_max 11 _diffrn_reflns_limit_l_min -13 _diffrn_reflns_limit_l_max 13 _diffrn_reflns_theta_min 1.98 _diffrn_reflns_theta_max 25.00 _reflns_number_total 2554 _reflns_number_gt 2465 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SMART' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'SHELXTL version 5.1 (Sheldrick, 1998)' _computing_structure_refinement 'SHELXTL version 5.1 (Sheldrick, 1998)' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0328P)^2^+2.2338P] 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 mixed _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 2554 _refine_ls_number_parameters 259 _refine_ls_number_restraints 14 _refine_ls_R_factor_all 0.0331 _refine_ls_R_factor_gt 0.0310 _refine_ls_wR_factor_ref 0.0728 _refine_ls_wR_factor_gt 0.0718 _refine_ls_goodness_of_fit_ref 1.166 _refine_ls_restrained_S_all 1.164 _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 La1 La -0.64962(4) 0.47067(3) 0.26928(2) 0.00944(10) Uani 1 1 d . . . N1 N -0.7670(5) 0.2385(4) 0.4753(4) 0.0109(8) Uani 1 1 d . . . C1 C -0.8664(6) 0.2674(5) 0.5853(4) 0.0108(9) Uani 1 1 d . . . C2 C -0.9510(7) 0.1652(5) 0.6942(4) 0.0131(10) Uani 1 1 d . . . H2 H -1.0244 0.1903 0.7700 0.016 Uiso 1 1 calc R . . C3 C -0.9244(7) 0.0263(5) 0.6878(4) 0.0122(9) Uani 1 1 d . . . C4 C -0.8172(7) -0.0059(5) 0.5745(4) 0.0125(9) Uani 1 1 d . . . H4 H -0.7956 -0.1012 0.5691 0.015 Uiso 1 1 calc R . . C5 C -0.7419(7) 0.1034(5) 0.4691(4) 0.0118(9) Uani 1 1 d . . . C6 C -0.6227(7) 0.0766(5) 0.3470(4) 0.0120(9) Uani 1 1 d . . . C7 C -0.5804(7) -0.0576(5) 0.3243(4) 0.0123(10) Uani 1 1 d . . . H7 H -0.6294 -0.1383 0.3894 0.015 Uiso 1 1 calc R . . C8 C -0.4669(6) -0.0729(5) 0.2068(4) 0.0113(9) Uani 1 1 d . . . C9 C -0.4003(7) 0.0485(5) 0.1138(5) 0.0126(9) Uani 1 1 d . . . H9 H -0.3253 0.0429 0.0312 0.015 Uiso 1 1 calc R . . C10 C -0.4448(7) 0.1772(5) 0.1434(4) 0.0116(9) Uani 1 1 d . . . N2 N -0.5523(5) 0.1926(4) 0.2567(4) 0.0110(8) Uani 1 1 d . . . C11 C -0.3733(6) 0.3125(5) 0.0471(4) 0.0120(9) Uani 1 1 d . . . O1 O -0.3831(5) 0.4147(3) 0.0954(3) 0.0129(7) Uani 1 1 d . . . O2 O -0.3128(5) 0.3145(3) -0.0683(3) 0.0135(7) Uani 1 1 d . . . C12 C -0.4151(7) -0.2200(5) 0.1828(4) 0.0124(10) Uani 1 1 d . . . O3 O -0.2899(5) -0.2353(3) 0.0839(3) 0.0162(7) Uani 1 1 d . . . O4 O -0.5034(5) -0.3184(3) 0.2651(3) 0.0156(7) Uani 1 1 d . . . C13 C -1.0013(7) -0.0953(5) 0.8001(5) 0.0132(10) Uani 1 1 d D . . O5 O -0.9566(5) -0.2175(3) 0.7923(3) 0.0193(8) Uani 1 1 d . . . O6 O -1.1102(5) -0.0572(4) 0.8976(3) 0.0224(8) Uani 1 1 d D . . H6 H -1.147(8) -0.128(4) 0.955(3) 0.027 Uiso 1 1 d D . . C14 C -0.8740(6) 0.4188(5) 0.5880(4) 0.0104(9) Uani 1 1 d . . . O7 O -0.9938(5) 0.4607(3) 0.6758(3) 0.0142(7) Uani 1 1 d . . . O8 O -0.7549(5) 0.4936(3) 0.5003(3) 0.0134(7) Uani 1 1 d . . . O1W O -0.8067(5) 0.4144(4) 0.1187(3) 0.0170(7) Uani 1 1 d D . . H1W1 H -0.886(6) 0.362(5) 0.125(5) 0.020 Uiso 1 1 d D . . H2W1 H -0.762(7) 0.445(5) 0.0411(18) 0.020 Uiso 1 1 d D . . O2W O -0.3559(5) 0.3536(4) 0.3717(3) 0.0170(7) Uani 1 1 d D . . H2W2 H -0.256(4) 0.334(6) 0.322(4) 0.020 Uiso 1 1 d D . . H1W2 H -0.330(7) 0.402(5) 0.412(5) 0.020 Uiso 1 1 d D . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 La1 0.01172(15) 0.00667(15) 0.00840(15) -0.00142(10) 0.00257(10) -0.00509(10) N1 0.0105(19) 0.0087(19) 0.013(2) -0.0031(15) 0.0001(16) -0.0032(15) C1 0.009(2) 0.011(2) 0.011(2) -0.0012(18) -0.0022(18) -0.0029(18) C2 0.012(2) 0.015(2) 0.009(2) -0.0022(19) 0.0033(18) -0.0043(19) C3 0.013(2) 0.012(2) 0.009(2) 0.0010(18) -0.0005(18) -0.0057(18) C4 0.015(2) 0.010(2) 0.010(2) -0.0011(18) 0.0022(19) -0.0044(19) C5 0.011(2) 0.010(2) 0.014(2) -0.0020(18) -0.0013(18) -0.0051(18) C6 0.012(2) 0.013(2) 0.010(2) -0.0023(18) 0.0007(18) -0.0046(19) C7 0.013(2) 0.010(2) 0.014(2) -0.0012(18) 0.0010(19) -0.0088(19) C8 0.009(2) 0.011(2) 0.013(2) -0.0031(18) 0.0008(18) -0.0052(18) C9 0.014(2) 0.011(2) 0.013(2) -0.0019(18) -0.0016(19) -0.0049(19) C10 0.013(2) 0.012(2) 0.009(2) -0.0020(18) 0.0001(19) -0.0048(19) N2 0.013(2) 0.0085(19) 0.0107(19) -0.0022(15) -0.0002(16) -0.0046(15) C11 0.008(2) 0.012(2) 0.014(2) -0.0016(19) 0.0005(18) -0.0041(18) O1 0.0176(17) 0.0086(16) 0.0105(16) -0.0017(13) 0.0017(13) -0.0048(13) O2 0.0177(17) 0.0107(16) 0.0091(16) -0.0017(13) 0.0045(13) -0.0063(13) C12 0.014(2) 0.012(2) 0.011(2) -0.0026(19) -0.0010(19) -0.0042(19) O3 0.0209(18) 0.0120(17) 0.0126(17) -0.0043(13) 0.0070(14) -0.0073(14) O4 0.0232(19) 0.0122(16) 0.0115(16) -0.0026(13) 0.0029(14) -0.0125(14) C13 0.011(2) 0.014(2) 0.014(2) -0.0032(19) -0.0004(19) -0.0040(19) O5 0.0235(19) 0.0122(18) 0.0179(18) -0.0037(14) 0.0092(15) -0.0113(15) O6 0.029(2) 0.0127(18) 0.0149(18) -0.0005(14) 0.0122(16) -0.0072(16) C14 0.009(2) 0.013(2) 0.008(2) 0.0005(18) -0.0025(18) -0.0031(18) O7 0.0152(17) 0.0131(17) 0.0128(16) -0.0049(13) 0.0028(14) -0.0039(14) O8 0.0170(17) 0.0141(16) 0.0087(16) -0.0031(13) 0.0028(13) -0.0085(14) O1W 0.0200(19) 0.0202(19) 0.0123(17) -0.0036(14) 0.0030(14) -0.0161(15) O2W 0.0210(19) 0.0144(18) 0.0174(18) -0.0082(14) 0.0003(15) -0.0060(15) _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 La1 O1 2.469(3) . ? La1 O1W 2.496(3) . ? La1 O7 2.504(3) 2_366 ? La1 O4 2.515(3) 1_565 ? La1 O8 2.548(3) . ? La1 O2W 2.571(4) . ? La1 O2 2.582(3) 2_465 ? La1 N2 2.759(4) . ? La1 N1 2.774(4) . ? N1 C1 1.333(6) . ? N1 C5 1.343(6) . ? C1 C2 1.396(6) . ? C1 C14 1.507(6) . ? C2 C3 1.380(7) . ? C3 C4 1.392(6) . ? C3 C13 1.508(6) . ? C4 C5 1.393(6) . ? C5 C6 1.479(6) . ? C6 N2 1.352(6) . ? C6 C7 1.399(6) . ? C7 C8 1.386(6) . ? C8 C9 1.391(6) . ? C8 C12 1.529(6) . ? C9 C10 1.380(6) . ? C10 N2 1.333(6) . ? C10 C11 1.515(6) . ? C11 O2 1.236(6) . ? C11 O1 1.275(6) . ? O2 La1 2.582(3) 2_465 ? C12 O4 1.256(6) . ? C12 O3 1.260(6) . ? O4 La1 2.515(3) 1_545 ? C13 O5 1.220(6) . ? C13 O6 1.281(6) . ? C14 O7 1.246(6) . ? C14 O8 1.266(6) . ? O7 La1 2.504(3) 2_366 ? 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 La1 O1W 74.74(11) . . ? O1 La1 O7 143.01(11) . 2_366 ? O1W La1 O7 70.00(11) . 2_366 ? O1 La1 O4 91.73(10) . 1_565 ? O1W La1 O4 135.09(11) . 1_565 ? O7 La1 O4 105.29(11) 2_366 1_565 ? O1 La1 O8 147.52(11) . . ? O1W La1 O8 135.17(11) . . ? O7 La1 O8 69.46(11) 2_366 . ? O4 La1 O8 74.55(10) 1_565 . ? O1 La1 O2W 72.45(11) . . ? O1W La1 O2W 134.24(11) . . ? O7 La1 O2W 142.80(11) 2_366 . ? O4 La1 O2W 77.01(11) 1_565 . ? O8 La1 O2W 75.78(11) . . ? O1 La1 O2 76.14(10) . 2_465 ? O1W La1 O2 67.94(11) . 2_465 ? O7 La1 O2 80.56(10) 2_366 2_465 ? O4 La1 O2 67.26(10) 1_565 2_465 ? O8 La1 O2 122.21(10) . 2_465 ? O2W La1 O2 130.97(11) . 2_465 ? O1 La1 N2 60.53(10) . . ? O1W La1 N2 66.40(12) . . ? O7 La1 N2 112.66(11) 2_366 . ? O4 La1 N2 141.72(11) 1_565 . ? O8 La1 N2 113.96(11) . . ? O2W La1 N2 69.96(11) . . ? O2 La1 N2 123.05(10) 2_465 . ? O1 La1 N1 115.68(10) . . ? O1W La1 N1 93.54(11) . . ? O7 La1 N1 77.88(11) 2_366 . ? O4 La1 N1 130.12(11) 1_565 . ? O8 La1 N1 59.83(10) . . ? O2W La1 N1 73.45(11) . . ? O2 La1 N1 155.46(11) 2_465 . ? N2 La1 N1 57.09(11) . . ? C1 N1 C5 118.7(4) . . ? C1 N1 La1 116.2(3) . . ? C5 N1 La1 124.9(3) . . ? N1 C1 C2 123.5(4) . . ? N1 C1 C14 115.3(4) . . ? C2 C1 C14 121.1(4) . . ? C3 C2 C1 117.6(4) . . ? C2 C3 C4 119.4(4) . . ? C2 C3 C13 123.0(4) . . ? C4 C3 C13 117.6(4) . . ? C3 C4 C5 119.2(4) . . ? N1 C5 C4 121.5(4) . . ? N1 C5 C6 116.2(4) . . ? C4 C5 C6 122.2(4) . . ? N2 C6 C7 121.2(4) . . ? N2 C6 C5 115.0(4) . . ? C7 C6 C5 123.9(4) . . ? C8 C7 C6 119.9(4) . . ? C7 C8 C9 118.0(4) . . ? C7 C8 C12 120.2(4) . . ? C9 C8 C12 121.8(4) . . ? C10 C9 C8 119.1(4) . . ? N2 C10 C9 123.3(4) . . ? N2 C10 C11 115.2(4) . . ? C9 C10 C11 121.5(4) . . ? C10 N2 C6 118.5(4) . . ? C10 N2 La1 115.1(3) . . ? C6 N2 La1 125.8(3) . . ? O2 C11 O1 126.4(4) . . ? O2 C11 C10 118.4(4) . . ? O1 C11 C10 115.2(4) . . ? C11 O1 La1 124.0(3) . . ? C11 O2 La1 126.8(3) . 2_465 ? O4 C12 O3 124.4(4) . . ? O4 C12 C8 116.4(4) . . ? O3 C12 C8 119.2(4) . . ? C12 O4 La1 138.4(3) . 1_545 ? O5 C13 O6 126.0(4) . . ? O5 C13 C3 119.6(4) . . ? O6 C13 C3 114.4(4) . . ? O7 C14 O8 125.0(4) . . ? O7 C14 C1 118.4(4) . . ? O8 C14 C1 116.6(4) . . ? C14 O7 La1 137.4(3) . 2_366 ? C14 O8 La1 123.0(3) . . ? 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 La1 N1 C1 160.6(3) . . . . ? O1W La1 N1 C1 -124.6(3) . . . . ? O7 La1 N1 C1 -55.9(3) 2_366 . . . ? O4 La1 N1 C1 44.0(4) 1_565 . . . ? O8 La1 N1 C1 17.2(3) . . . . ? O2W La1 N1 C1 100.1(3) . . . . ? O2 La1 N1 C1 -85.0(4) 2_465 . . . ? N2 La1 N1 C1 176.6(4) . . . . ? O1 La1 N1 C5 -23.9(4) . . . . ? O1W La1 N1 C5 50.9(4) . . . . ? O7 La1 N1 C5 119.5(4) 2_366 . . . ? O4 La1 N1 C5 -140.6(3) 1_565 . . . ? O8 La1 N1 C5 -167.3(4) . . . . ? O2W La1 N1 C5 -84.4(4) . . . . ? O2 La1 N1 C5 90.5(4) 2_465 . . . ? N2 La1 N1 C5 -7.9(3) . . . . ? C5 N1 C1 C2 -1.8(7) . . . . ? La1 N1 C1 C2 174.0(3) . . . . ? C5 N1 C1 C14 175.2(4) . . . . ? La1 N1 C1 C14 -9.0(5) . . . . ? N1 C1 C2 C3 2.0(7) . . . . ? C14 C1 C2 C3 -174.8(4) . . . . ? C1 C2 C3 C4 -0.5(7) . . . . ? C1 C2 C3 C13 177.6(4) . . . . ? C2 C3 C4 C5 -1.1(7) . . . . ? C13 C3 C4 C5 -179.3(4) . . . . ? C1 N1 C5 C4 0.0(7) . . . . ? La1 N1 C5 C4 -175.4(3) . . . . ? C1 N1 C5 C6 -177.2(4) . . . . ? La1 N1 C5 C6 7.4(6) . . . . ? C3 C4 C5 N1 1.4(7) . . . . ? C3 C4 C5 C6 178.5(4) . . . . ? N1 C5 C6 N2 0.5(6) . . . . ? C4 C5 C6 N2 -176.7(4) . . . . ? N1 C5 C6 C7 179.4(4) . . . . ? C4 C5 C6 C7 2.2(7) . . . . ? N2 C6 C7 C8 -1.0(7) . . . . ? C5 C6 C7 C8 -179.8(4) . . . . ? C6 C7 C8 C9 -0.8(7) . . . . ? C6 C7 C8 C12 178.2(4) . . . . ? C7 C8 C9 C10 1.9(7) . . . . ? C12 C8 C9 C10 -177.1(4) . . . . ? C8 C9 C10 N2 -1.2(7) . . . . ? C8 C9 C10 C11 178.8(4) . . . . ? C9 C10 N2 C6 -0.6(7) . . . . ? C11 C10 N2 C6 179.4(4) . . . . ? C9 C10 N2 La1 -172.5(4) . . . . ? C11 C10 N2 La1 7.4(5) . . . . ? C7 C6 N2 C10 1.7(7) . . . . ? C5 C6 N2 C10 -179.4(4) . . . . ? C7 C6 N2 La1 172.7(3) . . . . ? C5 C6 N2 La1 -8.4(6) . . . . ? O1 La1 N2 C10 -16.9(3) . . . . ? O1W La1 N2 C10 68.3(3) . . . . ? O7 La1 N2 C10 122.4(3) 2_366 . . . ? O4 La1 N2 C10 -65.6(4) 1_565 . . . ? O8 La1 N2 C10 -160.9(3) . . . . ? O2W La1 N2 C10 -97.6(3) . . . . ? O2 La1 N2 C10 29.0(4) 2_465 . . . ? N1 La1 N2 C10 179.6(4) . . . . ? O1 La1 N2 C6 171.8(4) . . . . ? O1W La1 N2 C6 -102.9(4) . . . . ? O7 La1 N2 C6 -48.9(4) 2_366 . . . ? O4 La1 N2 C6 123.1(3) 1_565 . . . ? O8 La1 N2 C6 27.8(4) . . . . ? O2W La1 N2 C6 91.2(4) . . . . ? O2 La1 N2 C6 -142.3(3) 2_465 . . . ? N1 La1 N2 C6 8.4(3) . . . . ? N2 C10 C11 O2 -163.4(4) . . . . ? C9 C10 C11 O2 16.6(7) . . . . ? N2 C10 C11 O1 16.4(6) . . . . ? C9 C10 C11 O1 -163.6(4) . . . . ? O2 C11 O1 La1 142.2(4) . . . . ? C10 C11 O1 La1 -37.6(5) . . . . ? O1W La1 O1 C11 -41.8(3) . . . . ? O7 La1 O1 C11 -59.7(4) 2_366 . . . ? O4 La1 O1 C11 -178.3(3) 1_565 . . . ? O8 La1 O1 C11 118.3(3) . . . . ? O2W La1 O1 C11 105.9(3) . . . . ? O2 La1 O1 C11 -112.3(4) 2_465 . . . ? N2 La1 O1 C11 29.4(3) . . . . ? N1 La1 O1 C11 44.8(4) . . . . ? O1 C11 O2 La1 -35.2(7) . . . 2_465 ? C10 C11 O2 La1 144.6(3) . . . 2_465 ? C7 C8 C12 O4 10.5(7) . . . . ? C9 C8 C12 O4 -170.6(4) . . . . ? C7 C8 C12 O3 -169.7(4) . . . . ? C9 C8 C12 O3 9.2(7) . . . . ? O3 C12 O4 La1 -38.9(8) . . . 1_545 ? C8 C12 O4 La1 140.9(4) . . . 1_545 ? C2 C3 C13 O5 -172.8(5) . . . . ? C4 C3 C13 O5 5.3(7) . . . . ? C2 C3 C13 O6 6.8(7) . . . . ? C4 C3 C13 O6 -175.1(4) . . . . ? N1 C1 C14 O7 166.0(4) . . . . ? C2 C1 C14 O7 -16.9(6) . . . . ? N1 C1 C14 O8 -14.7(6) . . . . ? C2 C1 C14 O8 162.4(4) . . . . ? O8 C14 O7 La1 107.2(5) . . . 2_366 ? C1 C14 O7 La1 -73.6(6) . . . 2_366 ? O7 C14 O8 La1 -145.6(4) . . . . ? C1 C14 O8 La1 35.1(5) . . . . ? O1 La1 O8 C14 -119.0(3) . . . . ? O1W La1 O8 C14 33.3(4) . . . . ? O7 La1 O8 C14 59.8(3) 2_366 . . . ? O4 La1 O8 C14 173.1(4) 1_565 . . . ? O2W La1 O8 C14 -106.7(4) . . . . ? O2 La1 O8 C14 123.5(3) 2_465 . . . ? N2 La1 O8 C14 -46.7(4) . . . . ? N1 La1 O8 C14 -27.8(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 O6 H6 O3 0.824(19) 1.72(2) 2.509(4) 161(5) 1_456 O1W H1W1 O5 0.819(14) 1.87(2) 2.641(4) 157(5) 2_356 O1W H2W1 O1 0.816(14) 1.94(3) 2.661(4) 147(5) 2_465 O2W H2W2 O5 0.815(14) 2.14(2) 2.917(5) 160(5) 2_456 O2W H1W2 O8 0.820(14) 1.907(16) 2.724(5) 175(5) 2_466 _diffrn_measured_fraction_theta_max 0.994 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 0.994 _refine_diff_density_max 1.806 _refine_diff_density_min -0.906 _refine_diff_density_rms 0.135 ####END data_3 _database_code_depnum_ccdc_archive 'CCDC 677291' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common 9 _chemical_melting_point ? _chemical_formula_moiety 'C14 H10 Eu N2 O12.50' _chemical_formula_sum 'C14 H10 Eu N2 O12.50' _chemical_formula_weight 558.20 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Eu Eu -0.1578 3.6682 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Orthorhombic _symmetry_space_group_name_H-M Pnma loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, -y, z+1/2' 'x+1/2, -y+1/2, -z+1/2' '-x, y+1/2, -z' '-x, -y, -z' 'x-1/2, y, -z-1/2' '-x-1/2, y-1/2, z-1/2' 'x, -y-1/2, z' _cell_length_a 21.9566(10) _cell_length_b 6.6188(3) _cell_length_c 11.3669(5) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 1651.91(13) _cell_formula_units_Z 4 _cell_measurement_temperature 153(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description prism _exptl_crystal_colour colourless _exptl_crystal_size_max 0.10 _exptl_crystal_size_mid 0.06 _exptl_crystal_size_min 0.03 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 2.244 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1084 _exptl_absorpt_coefficient_mu 3.877 _exptl_absorpt_correction_type empirical _exptl_absorpt_correction_T_min 0.7820 _exptl_absorpt_correction_T_max 1.0000 _exptl_absorpt_process_details sadabs _exptl_special_details ; ? ; _diffrn_ambient_temperature 153(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Bruker SMART APEX CCD' _diffrn_measurement_method 'Omega scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 12755 _diffrn_reflns_av_R_equivalents 0.0311 _diffrn_reflns_av_sigmaI/netI 0.0181 _diffrn_reflns_limit_h_min -25 _diffrn_reflns_limit_h_max 26 _diffrn_reflns_limit_k_min -7 _diffrn_reflns_limit_k_max 7 _diffrn_reflns_limit_l_min -13 _diffrn_reflns_limit_l_max 13 _diffrn_reflns_theta_min 1.85 _diffrn_reflns_theta_max 24.99 _reflns_number_total 1596 _reflns_number_gt 1570 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SMART' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'SHELXTL version 5.1 (Sheldrick, 1998)' _computing_structure_refinement 'SHELXTL version 5.1 (Sheldrick, 1998)' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0000P)^2^+62.2209P] 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 mixed _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 1596 _refine_ls_number_parameters 155 _refine_ls_number_restraints 136 _refine_ls_R_factor_all 0.0624 _refine_ls_R_factor_gt 0.0619 _refine_ls_wR_factor_ref 0.1544 _refine_ls_wR_factor_gt 0.1542 _refine_ls_goodness_of_fit_ref 1.423 _refine_ls_restrained_S_all 1.364 _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 Eu1 Eu 0.13148(3) -0.7500 0.46646(6) 0.0154(3) Uani 1 2 d S . . N1 N 0.2448(6) -0.7500 0.4223(11) 0.021(3) Uani 1 2 d SU . . C1 C 0.2625(7) -0.7500 0.3093(13) 0.020(4) Uani 1 2 d SU . . C2 C 0.3226(7) -0.7500 0.2749(14) 0.029(4) Uani 1 2 d SU . . H2A H 0.3336 -0.7500 0.1941 0.035 Uiso 1 2 calc SR . . C3 C 0.3670(8) -0.7500 0.3631(14) 0.039(5) Uani 1 2 d SU . . C4 C 0.3487(7) -0.7500 0.4815(15) 0.038(5) Uani 1 2 d SU . . H4A H 0.3782 -0.7500 0.5427 0.046 Uiso 1 2 calc SR . . C5 C 0.2870(7) -0.7500 0.5075(14) 0.025(4) Uani 1 2 d SU . . C6 C 0.2641(7) -0.7500 0.6295(14) 0.023(4) Uani 1 2 d SU . . C7 C 0.3016(6) -0.7500 0.7267(12) 0.010(3) Uiso 1 2 d SU . . H7A H 0.3445 -0.7500 0.7168 0.012 Uiso 1 2 calc SR . . C8 C 0.2769(7) -0.7500 0.8392(13) 0.018(3) Uani 1 2 d SU . . C9 C 0.2143(7) -0.7500 0.8502(15) 0.025(4) Uani 1 2 d SU . . H9A H 0.1960 -0.7500 0.9259 0.030 Uiso 1 2 calc SR . . C10 C 0.1784(7) -0.7500 0.7494(13) 0.018(3) Uani 1 2 d SU . . N2 N 0.2031(5) -0.7500 0.6403(11) 0.016(3) Uani 1 2 d SU . . C11 C 0.1093(8) -0.785(5) 0.7506(16) 0.018(7) Uani 0.50 1 d PU . . O1 O 0.0839(5) -0.7500 0.6510(10) 0.030(3) Uani 1 2 d SU . . O2 O 0.0829(6) -0.7500 0.8457(12) 0.035(3) Uiso 1 2 d SU . . C12 C 0.3205(7) -0.7500 0.9430(13) 0.022(4) Uani 1 2 d SU . . O3 O 0.3377(4) -0.9165(14) 0.9806(7) 0.028(2) Uani 1 1 d U . . C13 C 0.4330(9) -0.7500 0.3346(17) 0.031(4) Uiso 1 2 d SDU . . O4 O 0.4675(7) -0.7500 0.4264(13) 0.043(4) Uiso 1 2 d SDU . . H4 H 0.5049(11) -0.7500 0.410(6) 0.064 Uiso 1 2 d SD . . O5 O 0.4515(7) -0.7500 0.2322(14) 0.047(4) Uiso 1 2 d SU . . C14 C 0.2102(7) -0.7500 0.2218(13) 0.017(3) Uani 1 2 d SU . . O6 O 0.2222(5) -0.7500 0.1155(9) 0.024(3) Uani 1 2 d SU . . O7 O 0.1567(4) -0.7500 0.2650(9) 0.017(2) Uani 1 2 d SU . . O1W O 0.0438(4) -0.9614(16) 0.4052(11) 0.050(3) Uani 1 1 d . . . O2W O 0.0405(6) -0.331(2) 0.2232(11) 0.013(3) Uiso 0.50 1 d P . . O3W O 0.0792(6) -0.832(2) 1.0856(11) 0.012(3) Uiso 0.50 1 d P . . 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 0.0081(4) 0.0301(5) 0.0080(4) 0.000 -0.0001(3) 0.000 N1 0.010(6) 0.046(9) 0.007(6) 0.000 -0.001(5) 0.000 C1 0.010(7) 0.042(10) 0.007(7) 0.000 -0.004(6) 0.000 C2 0.011(7) 0.066(13) 0.010(7) 0.000 0.001(6) 0.000 C3 0.018(8) 0.088(14) 0.010(7) 0.000 0.000(7) 0.000 C4 0.012(7) 0.093(15) 0.009(7) 0.000 0.002(6) 0.000 C5 0.011(7) 0.054(11) 0.010(7) 0.000 0.000(6) 0.000 C6 0.011(7) 0.044(10) 0.013(7) 0.000 0.000(6) 0.000 C8 0.011(7) 0.030(9) 0.012(7) 0.000 0.002(6) 0.000 C9 0.016(8) 0.043(11) 0.016(8) 0.000 0.000(6) 0.000 C10 0.026(8) 0.018(8) 0.009(7) 0.000 0.006(6) 0.000 N2 0.009(6) 0.034(8) 0.007(6) 0.000 0.001(5) 0.000 C11 0.007(7) 0.03(2) 0.013(7) -0.011(10) 0.005(6) 0.003(9) O1 0.009(5) 0.069(10) 0.012(5) 0.000 0.000(4) 0.000 C12 0.004(6) 0.051(11) 0.010(7) 0.000 0.000(6) 0.000 O3 0.025(4) 0.044(5) 0.015(4) -0.006(4) -0.007(3) 0.018(4) C14 0.011(7) 0.032(9) 0.007(7) 0.000 -0.003(6) 0.000 O6 0.017(6) 0.049(8) 0.007(5) 0.000 0.002(4) 0.000 O7 0.011(5) 0.036(7) 0.005(5) 0.000 -0.001(4) 0.000 O1W 0.015(4) 0.036(6) 0.099(8) 0.033(6) -0.016(5) -0.009(4) _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 2.314(9) 7_665 ? Eu1 O3 2.314(9) 2_534 ? Eu1 O1 2.343(11) . ? Eu1 O7 2.356(10) . ? Eu1 O1W 2.480(9) . ? Eu1 O1W 2.480(9) 8_545 ? Eu1 N2 2.525(12) . ? Eu1 N1 2.537(12) . ? N1 C5 1.34(2) . ? N1 C1 1.342(19) . ? C1 C2 1.38(2) . ? C1 C14 1.519(19) . ? C2 C3 1.40(2) . ? C2 H2A 0.9500 . ? C3 C4 1.40(2) . ? C3 C13 1.48(3) . ? C4 C5 1.39(2) . ? C4 H4A 0.9500 . ? C5 C6 1.48(2) . ? C6 N2 1.346(19) . ? C6 C7 1.38(2) . ? C7 C8 1.39(2) . ? C7 H7A 0.9500 . ? C8 C9 1.38(2) . ? C8 C12 1.52(2) . ? C9 C10 1.39(2) . ? C9 H9A 0.9500 . ? C10 N2 1.352(19) . ? C10 C11 1.53(2) 8_545 ? C10 C11 1.53(2) . ? C11 C11 0.46(7) 8_545 ? C11 O2 1.25(2) . ? C11 O1 1.28(2) . ? O1 C11 1.28(2) 8_545 ? O2 C11 1.25(2) 8_545 ? C12 O3 1.241(11) 8_545 ? C12 O3 1.241(11) . ? O3 Eu1 2.314(9) 2_535 ? C13 O5 1.23(2) . ? C13 O4 1.29(2) . ? O4 H4 0.84(2) . ? C14 O6 1.236(18) . ? C14 O7 1.273(18) . ? O2W O2W 1.08(3) 8 ? O3W O3W 1.09(3) 8_545 ? 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 O3 145.0(4) 7_665 2_534 ? O3 Eu1 O1 93.9(2) 7_665 . ? O3 Eu1 O1 93.9(2) 2_534 . ? O3 Eu1 O7 89.9(2) 7_665 . ? O3 Eu1 O7 89.9(2) 2_534 . ? O1 Eu1 O7 167.1(4) . . ? O3 Eu1 O1W 141.7(3) 7_665 . ? O3 Eu1 O1W 73.1(3) 2_534 . ? O1 Eu1 O1W 84.5(4) . . ? O7 Eu1 O1W 84.8(3) . . ? O3 Eu1 O1W 73.1(3) 7_665 8_545 ? O3 Eu1 O1W 141.7(3) 2_534 8_545 ? O1 Eu1 O1W 84.5(4) . 8_545 ? O7 Eu1 O1W 84.8(3) . 8_545 ? O1W Eu1 O1W 68.7(4) . 8_545 ? O3 Eu1 N2 76.3(2) 7_665 . ? O3 Eu1 N2 76.3(2) 2_534 . ? O1 Eu1 N2 65.0(4) . . ? O7 Eu1 N2 127.9(4) . . ? O1W Eu1 N2 134.7(3) . . ? O1W Eu1 N2 134.7(3) 8_545 . ? O3 Eu1 N1 74.1(2) 7_665 . ? O3 Eu1 N1 74.1(2) 2_534 . ? O1 Eu1 N1 127.9(4) . . ? O7 Eu1 N1 65.0(4) . . ? O1W Eu1 N1 134.9(3) . . ? O1W Eu1 N1 134.9(3) 8_545 . ? N2 Eu1 N1 62.9(4) . . ? C5 N1 C1 119.3(13) . . ? C5 N1 Eu1 122.4(10) . . ? C1 N1 Eu1 118.3(9) . . ? N1 C1 C2 123.4(14) . . ? N1 C1 C14 114.0(13) . . ? C2 C1 C14 122.6(14) . . ? C1 C2 C3 117.7(15) . . ? C1 C2 H2A 121.1 . . ? C3 C2 H2A 121.1 . . ? C2 C3 C4 119.2(16) . . ? C2 C3 C13 121.6(15) . . ? C4 C3 C13 119.2(15) . . ? C5 C4 C3 118.9(15) . . ? C5 C4 H4A 120.6 . . ? C3 C4 H4A 120.6 . . ? N1 C5 C4 121.5(14) . . ? N1 C5 C6 116.3(13) . . ? C4 C5 C6 122.2(14) . . ? N2 C6 C7 121.4(14) . . ? N2 C6 C5 115.2(14) . . ? C7 C6 C5 123.4(14) . . ? C6 C7 C8 120.4(14) . . ? C6 C7 H7A 119.8 . . ? C8 C7 H7A 119.8 . . ? C9 C8 C7 118.2(14) . . ? C9 C8 C12 123.8(14) . . ? C7 C8 C12 118.0(13) . . ? C8 C9 C10 119.3(15) . . ? C8 C9 H9A 120.3 . . ? C10 C9 H9A 120.3 . . ? N2 C10 C9 121.9(15) . . ? N2 C10 C11 113.9(14) . 8_545 ? C9 C10 C11 123.5(14) . 8_545 ? N2 C10 C11 113.9(14) . . ? C9 C10 C11 123.5(14) . . ? C6 N2 C10 118.8(13) . . ? C6 N2 Eu1 123.2(10) . . ? C10 N2 Eu1 117.9(10) . . ? C11 C11 O2 79.3(16) 8_545 . ? C11 C11 O1 79.6(15) 8_545 . ? O2 C11 O1 121.9(17) . . ? C11 C11 C10 81.3(13) 8_545 . ? O2 C11 C10 116.1(17) . . ? O1 C11 C10 113.2(16) . . ? C11 O1 Eu1 126.6(10) . . ? C11 O1 Eu1 126.6(10) 8_545 . ? O3 C12 O3 125.4(14) 8_545 . ? O3 C12 C8 117.3(7) 8_545 . ? O3 C12 C8 117.3(7) . . ? C12 O3 Eu1 155.8(8) . 2_535 ? O5 C13 O4 124.8(18) . . ? O5 C13 C3 121.9(17) . . ? O4 C13 C3 113.4(16) . . ? C13 O4 H4 113(5) . . ? O6 C14 O7 124.9(13) . . ? O6 C14 C1 118.7(13) . . ? O7 C14 C1 116.4(12) . . ? C14 O7 Eu1 126.3(9) . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag O3 Eu1 N1 C5 82.5(2) 7_665 . . . ? O3 Eu1 N1 C5 -82.5(2) 2_534 . . . ? O1 Eu1 N1 C5 0.000(1) . . . . ? O7 Eu1 N1 C5 180.000(1) . . . . ? O1W Eu1 N1 C5 -127.2(4) . . . . ? O1W Eu1 N1 C5 127.2(4) 8_545 . . . ? N2 Eu1 N1 C5 0.000(1) . . . . ? O3 Eu1 N1 C1 -97.5(2) 7_665 . . . ? O3 Eu1 N1 C1 97.5(2) 2_534 . . . ? O1 Eu1 N1 C1 180.0 . . . . ? O7 Eu1 N1 C1 0.0 . . . . ? O1W Eu1 N1 C1 52.8(4) . . . . ? O1W Eu1 N1 C1 -52.8(4) 8_545 . . . ? N2 Eu1 N1 C1 180.000(1) . . . . ? C5 N1 C1 C2 0.000(2) . . . . ? Eu1 N1 C1 C2 180.0 . . . . ? C5 N1 C1 C14 180.000(1) . . . . ? Eu1 N1 C1 C14 0.000(1) . . . . ? N1 C1 C2 C3 0.000(2) . . . . ? C14 C1 C2 C3 180.000(1) . . . . ? C1 C2 C3 C4 0.000(2) . . . . ? C1 C2 C3 C13 180.000(1) . . . . ? C2 C3 C4 C5 0.000(2) . . . . ? C13 C3 C4 C5 180.000(2) . . . . ? C1 N1 C5 C4 0.000(2) . . . . ? Eu1 N1 C5 C4 180.000(2) . . . . ? C1 N1 C5 C6 180.000(2) . . . . ? Eu1 N1 C5 C6 0.000(2) . . . . ? C3 C4 C5 N1 0.000(2) . . . . ? C3 C4 C5 C6 180.000(2) . . . . ? N1 C5 C6 N2 0.000(2) . . . . ? C4 C5 C6 N2 180.000(2) . . . . ? N1 C5 C6 C7 180.000(2) . . . . ? C4 C5 C6 C7 0.000(3) . . . . ? N2 C6 C7 C8 0.000(4) . . . . ? C5 C6 C7 C8 180.000(3) . . . . ? C6 C7 C8 C9 0.000(4) . . . . ? C6 C7 C8 C12 180.000(3) . . . . ? C7 C8 C9 C10 0.000(4) . . . . ? C12 C8 C9 C10 180.000(3) . . . . ? C8 C9 C10 N2 0.000(4) . . . . ? C8 C9 C10 C11 -169.6(15) . . . 8_545 ? C8 C9 C10 C11 169.6(15) . . . . ? C7 C6 N2 C10 0.000(4) . . . . ? C5 C6 N2 C10 180.000(3) . . . . ? C7 C6 N2 Eu1 180.000(2) . . . . ? C5 C6 N2 Eu1 0.000(2) . . . . ? C9 C10 N2 C6 0.000(4) . . . . ? C11 C10 N2 C6 170.5(14) 8_545 . . . ? C11 C10 N2 C6 -170.5(14) . . . . ? C9 C10 N2 Eu1 180.000(3) . . . . ? C11 C10 N2 Eu1 -9.5(14) 8_545 . . . ? C11 C10 N2 Eu1 9.5(14) . . . . ? O3 Eu1 N2 C6 -79.0(2) 7_665 . . . ? O3 Eu1 N2 C6 79.0(2) 2_534 . . . ? O1 Eu1 N2 C6 180.000(2) . . . . ? O7 Eu1 N2 C6 0.000(2) . . . . ? O1W Eu1 N2 C6 127.5(4) . . . . ? O1W Eu1 N2 C6 -127.5(4) 8_545 . . . ? N1 Eu1 N2 C6 0.000(2) . . . . ? O3 Eu1 N2 C10 101.0(2) 7_665 . . . ? O3 Eu1 N2 C10 -101.0(2) 2_534 . . . ? O1 Eu1 N2 C10 0.000(2) . . . . ? O7 Eu1 N2 C10 180.000(2) . . . . ? O1W Eu1 N2 C10 -52.5(4) . . . . ? O1W Eu1 N2 C10 52.5(4) 8_545 . . . ? N1 Eu1 N2 C10 180.000(2) . . . . ? N2 C10 C11 C11 -93.9(6) . . . 8_545 ? C9 C10 C11 C11 95.8(9) . . . 8_545 ? N2 C10 C11 O2 -167.4(18) . . . . ? C9 C10 C11 O2 22(3) . . . . ? C11 C10 C11 O2 -74(2) 8_545 . . . ? N2 C10 C11 O1 -19(3) . . . . ? C9 C10 C11 O1 170.5(13) . . . . ? C11 C10 C11 O1 75(2) 8_545 . . . ? O2 C11 O1 C11 70(3) . . . 8_545 ? C10 C11 O1 C11 -76(2) . . . 8_545 ? C11 C11 O1 Eu1 97.8(12) 8_545 . . . ? O2 C11 O1 Eu1 168.2(16) . . . . ? C10 C11 O1 Eu1 22(3) . . . . ? O3 Eu1 O1 C11 -85.9(19) 7_665 . . . ? O3 Eu1 O1 C11 60.0(19) 2_534 . . . ? O7 Eu1 O1 C11 167.0(19) . . . . ? O1W Eu1 O1 C11 132.5(19) . . . . ? O1W Eu1 O1 C11 -158.4(19) 8_545 . . . ? N2 Eu1 O1 C11 -13.0(19) . . . . ? N1 Eu1 O1 C11 -13.0(19) . . . . ? O3 Eu1 O1 C11 -60.0(19) 7_665 . . 8_545 ? O3 Eu1 O1 C11 85.9(19) 2_534 . . 8_545 ? O7 Eu1 O1 C11 -167.0(19) . . . 8_545 ? O1W Eu1 O1 C11 158.4(19) . . . 8_545 ? O1W Eu1 O1 C11 -132.5(19) 8_545 . . 8_545 ? N2 Eu1 O1 C11 13.0(19) . . . 8_545 ? N1 Eu1 O1 C11 13.0(19) . . . 8_545 ? O1 C11 O2 C11 -71(3) . . . 8_545 ? C10 C11 O2 C11 75(2) . . . 8_545 ? C9 C8 C12 O3 -91.2(12) . . . 8_545 ? C7 C8 C12 O3 88.8(12) . . . 8_545 ? C9 C8 C12 O3 91.2(12) . . . . ? C7 C8 C12 O3 -88.8(12) . . . . ? O3 C12 O3 Eu1 -139.6(12) 8_545 . . 2_535 ? C8 C12 O3 Eu1 38(3) . . . 2_535 ? C2 C3 C13 O5 0.000(2) . . . . ? C4 C3 C13 O5 180.000(2) . . . . ? C2 C3 C13 O4 180.000(1) . . . . ? C4 C3 C13 O4 0.000(2) . . . . ? N1 C1 C14 O6 180.000(1) . . . . ? C2 C1 C14 O6 0.000(1) . . . . ? N1 C1 C14 O7 0.000(1) . . . . ? C2 C1 C14 O7 180.0 . . . . ? O6 C14 O7 Eu1 180.0 . . . . ? C1 C14 O7 Eu1 0.0 . . . . ? O3 Eu1 O7 C14 72.5(2) 7_665 . . . ? O3 Eu1 O7 C14 -72.5(2) 2_534 . . . ? O1 Eu1 O7 C14 180.000(1) . . . . ? O1W Eu1 O7 C14 -145.5(2) . . . . ? O1W Eu1 O7 C14 145.5(2) 8_545 . . . ? N2 Eu1 O7 C14 0.0 . . . . ? N1 Eu1 O7 C14 0.0 . . . . ? 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 O4 H4 O3W 0.84(2) 1.72(3) 2.517(19) 157(4) 6_657 O4 H4 O3W 0.84(2) 1.72(3) 2.517(19) 157(4) 3_536 _diffrn_measured_fraction_theta_max 1.000 _diffrn_reflns_theta_full 24.99 _diffrn_measured_fraction_theta_full 1.000 _refine_diff_density_max 2.197 _refine_diff_density_min -1.749 _refine_diff_density_rms 0.260 ####END data_5 _database_code_depnum_ccdc_archive 'CCDC 677292' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common 11 _chemical_melting_point ? _chemical_formula_moiety 'C14 H6 Eu N2 O9, C2 H8 N' _chemical_formula_sum 'C16 H14 Eu N3 O9' _chemical_formula_weight 544.26 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Eu Eu -0.1578 3.6682 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Monoclinic _symmetry_space_group_name_H-M P2(1)/c loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y-1/2, z-1/2' _cell_length_a 8.2797(4) _cell_length_b 16.7532(9) _cell_length_c 12.7089(6) _cell_angle_alpha 90.00 _cell_angle_beta 97.5780(10) _cell_angle_gamma 90.00 _cell_volume 1747.47(15) _cell_formula_units_Z 4 _cell_measurement_temperature 153(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description block _exptl_crystal_colour colourless _exptl_crystal_size_max 0.16 _exptl_crystal_size_mid 0.152 _exptl_crystal_size_min 0.06 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 2.069 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1064 _exptl_absorpt_coefficient_mu 3.650 _exptl_absorpt_correction_type empirical _exptl_absorpt_correction_T_min 0.7486 _exptl_absorpt_correction_T_max 1.000 _exptl_absorpt_process_details SADABS _exptl_special_details ; ? ; _diffrn_ambient_temperature 153(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Bruker SMART APEX CCD' _diffrn_measurement_method 'omega scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 13473 _diffrn_reflns_av_R_equivalents 0.0311 _diffrn_reflns_av_sigmaI/netI 0.0200 _diffrn_reflns_limit_h_min -9 _diffrn_reflns_limit_h_max 9 _diffrn_reflns_limit_k_min -19 _diffrn_reflns_limit_k_max 19 _diffrn_reflns_limit_l_min -15 _diffrn_reflns_limit_l_max 15 _diffrn_reflns_theta_min 2.02 _diffrn_reflns_theta_max 25.00 _reflns_number_total 3064 _reflns_number_gt 2955 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SMART' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'SHELXTL version 5.1 (Sheldrick, 1998)' _computing_structure_refinement 'SHELXTL version 5.1 (Sheldrick, 1998)' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0151P)^2^+2.0737P] 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 mixed _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 3064 _refine_ls_number_parameters 278 _refine_ls_number_restraints 3 _refine_ls_R_factor_all 0.0172 _refine_ls_R_factor_gt 0.0164 _refine_ls_wR_factor_ref 0.0404 _refine_ls_wR_factor_gt 0.0400 _refine_ls_goodness_of_fit_ref 1.103 _refine_ls_restrained_S_all 1.104 _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 0.413742(13) 0.728233(6) 0.410989(8) 0.01070(5) Uani 1 1 d . . . N1 N 0.4365(2) 0.61344(11) 0.27894(15) 0.0126(4) Uani 1 1 d . . . C1 C 0.5052(3) 0.63325(14) 0.19297(18) 0.0134(5) Uani 1 1 d . . . C2 C 0.5719(3) 0.57731(14) 0.13180(18) 0.0135(5) Uani 1 1 d . . . H2 H 0.6224 0.5934 0.0723 0.016 Uiso 1 1 calc R . . C3 C 0.5640(3) 0.49719(14) 0.15828(18) 0.0130(5) Uani 1 1 d . . . C4 C 0.4840(3) 0.47539(13) 0.24390(17) 0.0122(5) Uani 1 1 d . . . H4 H 0.4713 0.4208 0.2612 0.015 Uiso 1 1 calc R . . C5 C 0.4234(3) 0.53547(14) 0.30329(18) 0.0117(5) Uani 1 1 d . . . C6 C 0.3420(3) 0.52134(14) 0.40040(18) 0.0120(5) Uani 1 1 d . . . C7 C 0.3097(3) 0.44593(14) 0.43826(18) 0.0134(5) Uani 1 1 d . . . H7 H 0.3411 0.3992 0.4038 0.016 Uiso 1 1 calc R . . C8 C 0.2299(3) 0.44049(14) 0.52833(18) 0.0133(5) Uani 1 1 d . . . C9 C 0.1794(3) 0.51001(14) 0.57301(18) 0.0132(5) Uani 1 1 d . . . H9 H 0.1173 0.5078 0.6307 0.016 Uiso 1 1 calc R . . C10 C 0.2205(3) 0.58249(14) 0.53263(18) 0.0128(5) Uani 1 1 d . . . N2 N 0.3042(2) 0.58875(12) 0.44972(15) 0.0125(4) Uani 1 1 d . . . C11 C 0.1704(3) 0.66108(14) 0.57848(18) 0.0130(5) Uani 1 1 d . . . C12 C 0.2020(3) 0.36085(15) 0.58006(18) 0.0145(5) Uani 1 1 d . . . O1 O 0.2195(2) 0.72378(9) 0.53564(13) 0.0142(4) Uani 1 1 d . . . O2 O 0.0852(2) 0.65840(10) 0.65112(14) 0.0201(4) Uani 1 1 d . . . O4 O 0.3129(2) 0.30942(10) 0.57846(13) 0.0161(4) Uani 1 1 d . . . C13 C 0.6493(3) 0.43663(14) 0.09630(18) 0.0137(5) Uani 1 1 d . . . O5 O 0.5978(2) 0.36600(11) 0.09413(12) 0.0173(4) Uani 1 1 d . . . O6 O 0.7628(2) 0.46231(11) 0.05073(16) 0.0259(4) Uani 1 1 d . . . C14 C 0.5122(3) 0.72205(14) 0.17005(19) 0.0132(5) Uani 1 1 d . . . O7 O 0.5532(2) 0.74221(11) 0.08233(12) 0.0147(3) Uani 1 1 d . . . O8 O 0.4768(2) 0.76886(9) 0.24036(13) 0.0160(4) Uani 1 1 d . . . O1W O 0.1484(2) 0.74124(12) 0.31295(15) 0.0207(4) Uani 1 1 d D . . H2W1 H 0.068(3) 0.7171(18) 0.326(3) 0.035(10) Uiso 1 1 d D . . H1W1 H 0.120(4) 0.7683(16) 0.2600(19) 0.027(9) Uiso 1 1 d D . . N3 N 0.9912(3) 0.35465(17) 0.0129(3) 0.0420(8) Uani 1 1 d . . . H1N3 H 0.908(4) 0.389(2) 0.024(2) 0.032(8) Uiso 1 1 d . . . H2N3 H 0.952(4) 0.308(2) 0.027(3) 0.046(10) Uiso 1 1 d . . . C15 C 1.0306(5) 0.3629(2) -0.0965(3) 0.0607(12) Uani 1 1 d . . . H15C H 0.9330 0.3521 -0.1470 0.091 Uiso 1 1 calc R . . H15B H 1.1164 0.3248 -0.1080 0.091 Uiso 1 1 calc R . . H15A H 1.0686 0.4174 -0.1073 0.091 Uiso 1 1 calc R . . C16 C 1.1295(4) 0.3708(2) 0.0958(3) 0.0515(10) Uani 1 1 d . . . H16C H 1.0938 0.3651 0.1660 0.077 Uiso 1 1 calc R . . H16B H 1.1692 0.4252 0.0876 0.077 Uiso 1 1 calc R . . H16A H 1.2174 0.3327 0.0891 0.077 Uiso 1 1 calc R . . O3 O 0.0759(2) 0.35387(11) 0.62158(16) 0.0248(4) Uani 1 1 d . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 Eu1 0.01539(8) 0.00778(8) 0.00960(7) 0.00007(4) 0.00417(5) -0.00004(4) N1 0.0171(10) 0.0089(10) 0.0117(10) 0.0000(8) 0.0021(8) -0.0013(8) C1 0.0157(11) 0.0128(12) 0.0114(11) 0.0008(9) 0.0008(9) -0.0005(9) C2 0.0140(11) 0.0161(12) 0.0106(11) 0.0008(10) 0.0029(9) -0.0014(9) C3 0.0135(11) 0.0111(11) 0.0139(11) -0.0010(9) 0.0005(9) -0.0010(9) C4 0.0142(11) 0.0100(12) 0.0125(11) -0.0005(9) 0.0020(9) -0.0021(9) C5 0.0137(11) 0.0104(11) 0.0110(11) 0.0018(9) 0.0009(9) -0.0020(9) C6 0.0128(11) 0.0128(12) 0.0103(11) 0.0005(9) 0.0013(9) -0.0003(9) C7 0.0143(11) 0.0124(12) 0.0135(11) -0.0012(9) 0.0017(9) 0.0016(9) C8 0.0101(11) 0.0162(12) 0.0128(11) 0.0029(9) -0.0008(9) -0.0008(9) C9 0.0124(11) 0.0163(12) 0.0114(11) -0.0001(9) 0.0037(9) -0.0003(9) C10 0.0131(11) 0.0143(12) 0.0108(11) 0.0013(9) 0.0014(9) 0.0013(9) N2 0.0144(10) 0.0121(10) 0.0112(9) 0.0000(8) 0.0019(7) 0.0004(8) C11 0.0154(12) 0.0119(12) 0.0113(11) -0.0013(9) 0.0003(9) 0.0002(9) C12 0.0177(12) 0.0146(12) 0.0107(11) -0.0008(9) 0.0003(9) -0.0025(10) O1 0.0188(9) 0.0104(8) 0.0146(8) 0.0007(6) 0.0059(7) 0.0005(6) O2 0.0268(9) 0.0170(9) 0.0194(9) -0.0038(7) 0.0134(7) -0.0036(7) O4 0.0199(9) 0.0126(9) 0.0167(8) 0.0017(7) 0.0058(7) 0.0029(7) C13 0.0175(12) 0.0113(12) 0.0121(11) -0.0002(9) 0.0008(9) 0.0000(10) O5 0.0248(9) 0.0127(9) 0.0155(9) -0.0004(7) 0.0061(7) 0.0000(7) O6 0.0275(10) 0.0171(9) 0.0372(11) -0.0051(8) 0.0195(9) -0.0022(8) C14 0.0144(12) 0.0131(12) 0.0118(12) 0.0008(9) 0.0012(9) 0.0004(9) O7 0.0193(8) 0.0138(9) 0.0117(8) 0.0025(7) 0.0050(7) -0.0007(7) O8 0.0277(10) 0.0091(9) 0.0122(8) -0.0003(7) 0.0067(7) 0.0013(7) O1W 0.0183(9) 0.0246(10) 0.0184(9) 0.0105(8) -0.0005(7) -0.0065(8) N3 0.0280(14) 0.0204(14) 0.083(2) -0.0179(14) 0.0291(14) -0.0080(12) C15 0.050(2) 0.058(2) 0.082(3) -0.045(2) 0.039(2) -0.0299(19) C16 0.0319(18) 0.0306(19) 0.093(3) 0.0107(19) 0.0110(18) 0.0003(15) O3 0.0186(9) 0.0215(10) 0.0374(11) 0.0122(9) 0.0149(8) 0.0021(7) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag Eu1 O5 2.3106(18) 2_655 ? Eu1 O4 2.3364(16) 3_666 ? Eu1 O7 2.3784(16) 4_576 ? Eu1 O1W 2.3887(18) . ? Eu1 O8 2.3953(16) . ? Eu1 O1 2.4026(16) . ? Eu1 N1 2.5756(19) . ? Eu1 N2 2.578(2) . ? N1 C1 1.339(3) . ? N1 C5 1.350(3) . ? C1 C2 1.378(3) . ? C1 C14 1.519(3) . ? C2 C3 1.387(3) . ? C3 C4 1.395(3) . ? C3 C13 1.515(3) . ? C4 C5 1.391(3) . ? C5 C6 1.501(3) . ? C6 N2 1.348(3) . ? C6 C7 1.390(3) . ? C7 C8 1.398(3) . ? C8 C9 1.384(3) . ? C8 C12 1.519(3) . ? C9 C10 1.378(3) . ? C10 N2 1.339(3) . ? C10 C11 1.520(3) . ? C11 O2 1.234(3) . ? C11 O1 1.274(3) . ? C12 O3 1.235(3) . ? C12 O4 1.261(3) . ? O4 Eu1 2.3364(16) 3_666 ? C13 O6 1.244(3) . ? C13 O5 1.257(3) . ? O5 Eu1 2.3106(18) 2_645 ? C14 O8 1.252(3) . ? C14 O7 1.254(3) . ? O7 Eu1 2.3784(16) 4_575 ? N3 C16 1.476(5) . ? N3 C15 1.476(5) . ? 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 O4 107.92(6) 2_655 3_666 ? O5 Eu1 O7 80.28(6) 2_655 4_576 ? O4 Eu1 O7 69.76(6) 3_666 4_576 ? O5 Eu1 O1W 82.08(6) 2_655 . ? O4 Eu1 O1W 150.70(6) 3_666 . ? O7 Eu1 O1W 139.52(6) 4_576 . ? O5 Eu1 O8 72.77(5) 2_655 . ? O4 Eu1 O8 78.66(6) 3_666 . ? O7 Eu1 O8 129.21(6) 4_576 . ? O1W Eu1 O8 78.31(6) . . ? O5 Eu1 O1 91.19(5) 2_655 . ? O4 Eu1 O1 132.94(6) 3_666 . ? O7 Eu1 O1 71.89(6) 4_576 . ? O1W Eu1 O1 72.37(6) . . ? O8 Eu1 O1 148.28(6) . . ? O5 Eu1 N1 137.21(6) 2_655 . ? O4 Eu1 N1 71.47(6) 3_666 . ? O7 Eu1 N1 133.12(6) 4_576 . ? O1W Eu1 N1 82.51(6) . . ? O8 Eu1 N1 65.09(6) . . ? O1 Eu1 N1 121.28(6) . . ? O5 Eu1 N2 153.72(6) 2_655 . ? O4 Eu1 N2 96.14(6) 3_666 . ? O7 Eu1 N2 98.89(6) 4_576 . ? O1W Eu1 N2 81.93(6) . . ? O8 Eu1 N2 123.70(6) . . ? O1 Eu1 N2 64.08(6) . . ? N1 Eu1 N2 60.35(6) . . ? C1 N1 C5 118.9(2) . . ? C1 N1 Eu1 114.98(15) . . ? C5 N1 Eu1 123.92(15) . . ? N1 C1 C2 122.5(2) . . ? N1 C1 C14 115.5(2) . . ? C2 C1 C14 122.0(2) . . ? C1 C2 C3 119.1(2) . . ? C2 C3 C4 119.0(2) . . ? C2 C3 C13 118.8(2) . . ? C4 C3 C13 122.1(2) . . ? C5 C4 C3 118.4(2) . . ? N1 C5 C4 122.0(2) . . ? N1 C5 C6 113.5(2) . . ? C4 C5 C6 124.4(2) . . ? N2 C6 C7 122.2(2) . . ? N2 C6 C5 114.0(2) . . ? C7 C6 C5 123.7(2) . . ? C6 C7 C8 118.4(2) . . ? C9 C8 C7 118.8(2) . . ? C9 C8 C12 119.3(2) . . ? C7 C8 C12 121.8(2) . . ? C10 C9 C8 119.0(2) . . ? N2 C10 C9 122.7(2) . . ? N2 C10 C11 115.4(2) . . ? C9 C10 C11 121.8(2) . . ? C10 N2 C6 118.4(2) . . ? C10 N2 Eu1 116.92(15) . . ? C6 N2 Eu1 124.14(15) . . ? O2 C11 O1 126.6(2) . . ? O2 C11 C10 117.9(2) . . ? O1 C11 C10 115.56(19) . . ? O3 C12 O4 126.9(2) . . ? O3 C12 C8 117.0(2) . . ? O4 C12 C8 116.1(2) . . ? C11 O1 Eu1 125.92(14) . . ? C12 O4 Eu1 152.30(16) . 3_666 ? O6 C13 O5 126.2(2) . . ? O6 C13 C3 116.3(2) . . ? O5 C13 C3 117.5(2) . . ? C13 O5 Eu1 162.53(16) . 2_645 ? O8 C14 O7 125.6(2) . . ? O8 C14 C1 117.3(2) . . ? O7 C14 C1 117.1(2) . . ? C14 O7 Eu1 135.58(15) . 4_575 ? C14 O8 Eu1 124.57(14) . . ? C16 N3 C15 114.1(3) . . ? 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 O5 Eu1 N1 C1 24.6(2) 2_655 . . . ? O4 Eu1 N1 C1 -72.04(16) 3_666 . . . ? O7 Eu1 N1 C1 -107.57(16) 4_576 . . . ? O1W Eu1 N1 C1 94.31(16) . . . . ? O8 Eu1 N1 C1 13.77(15) . . . . ? O1 Eu1 N1 C1 158.38(15) . . . . ? N2 Eu1 N1 C1 179.26(18) . . . . ? O5 Eu1 N1 C5 -172.67(15) 2_655 . . . ? O4 Eu1 N1 C5 90.69(18) 3_666 . . . ? O7 Eu1 N1 C5 55.2(2) 4_576 . . . ? O1W Eu1 N1 C5 -102.95(18) . . . . ? O8 Eu1 N1 C5 176.50(19) . . . . ? O1 Eu1 N1 C5 -38.89(19) . . . . ? N2 Eu1 N1 C5 -18.01(16) . . . . ? C5 N1 C1 C2 -3.9(3) . . . . ? Eu1 N1 C1 C2 159.76(18) . . . . ? C5 N1 C1 C14 178.8(2) . . . . ? Eu1 N1 C1 C14 -17.5(2) . . . . ? N1 C1 C2 C3 1.7(4) . . . . ? C14 C1 C2 C3 178.8(2) . . . . ? C1 C2 C3 C4 2.2(3) . . . . ? C1 C2 C3 C13 -175.1(2) . . . . ? C2 C3 C4 C5 -3.7(3) . . . . ? C13 C3 C4 C5 173.5(2) . . . . ? C1 N1 C5 C4 2.2(3) . . . . ? Eu1 N1 C5 C4 -159.89(17) . . . . ? C1 N1 C5 C6 -179.1(2) . . . . ? Eu1 N1 C5 C6 18.8(3) . . . . ? C3 C4 C5 N1 1.6(3) . . . . ? C3 C4 C5 C6 -176.9(2) . . . . ? N1 C5 C6 N2 -3.4(3) . . . . ? C4 C5 C6 N2 175.2(2) . . . . ? N1 C5 C6 C7 177.5(2) . . . . ? C4 C5 C6 C7 -3.9(4) . . . . ? N2 C6 C7 C8 2.4(3) . . . . ? C5 C6 C7 C8 -178.6(2) . . . . ? C6 C7 C8 C9 3.1(3) . . . . ? C6 C7 C8 C12 -175.0(2) . . . . ? C7 C8 C9 C10 -5.1(3) . . . . ? C12 C8 C9 C10 173.1(2) . . . . ? C8 C9 C10 N2 1.8(4) . . . . ? C8 C9 C10 C11 -179.5(2) . . . . ? C9 C10 N2 C6 3.6(3) . . . . ? C11 C10 N2 C6 -175.2(2) . . . . ? C9 C10 N2 Eu1 -168.66(17) . . . . ? C11 C10 N2 Eu1 12.5(2) . . . . ? C7 C6 N2 C10 -5.7(3) . . . . ? C5 C6 N2 C10 175.2(2) . . . . ? C7 C6 N2 Eu1 165.95(17) . . . . ? C5 C6 N2 Eu1 -13.1(3) . . . . ? O5 Eu1 N2 C10 -33.4(2) 2_655 . . . ? O4 Eu1 N2 C10 123.01(16) 3_666 . . . ? O7 Eu1 N2 C10 52.61(16) 4_576 . . . ? O1W Eu1 N2 C10 -86.46(16) . . . . ? O8 Eu1 N2 C10 -156.54(15) . . . . ? O1 Eu1 N2 C10 -12.19(15) . . . . ? N1 Eu1 N2 C10 -172.39(18) . . . . ? O5 Eu1 N2 C6 154.78(16) 2_655 . . . ? O4 Eu1 N2 C6 -48.78(18) 3_666 . . . ? O7 Eu1 N2 C6 -119.19(17) 4_576 . . . ? O1W Eu1 N2 C6 101.75(18) . . . . ? O8 Eu1 N2 C6 31.7(2) . . . . ? O1 Eu1 N2 C6 176.02(19) . . . . ? N1 Eu1 N2 C6 15.81(16) . . . . ? N2 C10 C11 O2 176.0(2) . . . . ? C9 C10 C11 O2 -2.8(3) . . . . ? N2 C10 C11 O1 -2.8(3) . . . . ? C9 C10 C11 O1 178.3(2) . . . . ? C9 C8 C12 O3 35.1(3) . . . . ? C7 C8 C12 O3 -146.8(2) . . . . ? C9 C8 C12 O4 -143.1(2) . . . . ? C7 C8 C12 O4 35.1(3) . . . . ? O2 C11 O1 Eu1 171.28(17) . . . . ? C10 C11 O1 Eu1 -10.0(3) . . . . ? O5 Eu1 O1 C11 -177.34(18) 2_655 . . . ? O4 Eu1 O1 C11 -61.3(2) 3_666 . . . ? O7 Eu1 O1 C11 -97.96(18) 4_576 . . . ? O1W Eu1 O1 C11 101.36(19) . . . . ? O8 Eu1 O1 C11 124.66(18) . . . . ? N1 Eu1 O1 C11 32.0(2) . . . . ? N2 Eu1 O1 C11 11.89(17) . . . . ? O3 C12 O4 Eu1 -140.0(3) . . . 3_666 ? C8 C12 O4 Eu1 37.9(4) . . . 3_666 ? C2 C3 C13 O6 23.0(3) . . . . ? C4 C3 C13 O6 -154.2(2) . . . . ? C2 C3 C13 O5 -155.9(2) . . . . ? C4 C3 C13 O5 26.9(3) . . . . ? O6 C13 O5 Eu1 34.6(7) . . . 2_645 ? C3 C13 O5 Eu1 -146.6(4) . . . 2_645 ? N1 C1 C14 O8 10.5(3) . . . . ? C2 C1 C14 O8 -166.8(2) . . . . ? N1 C1 C14 O7 -169.7(2) . . . . ? C2 C1 C14 O7 13.0(3) . . . . ? O8 C14 O7 Eu1 -87.6(3) . . . 4_575 ? C1 C14 O7 Eu1 92.6(3) . . . 4_575 ? O7 C14 O8 Eu1 -176.33(17) . . . . ? C1 C14 O8 Eu1 3.5(3) . . . . ? O5 Eu1 O8 C14 178.7(2) 2_655 . . . ? O4 Eu1 O8 C14 65.71(19) 3_666 . . . ? O7 Eu1 O8 C14 117.46(19) 4_576 . . . ? O1W Eu1 O8 C14 -96.06(19) . . . . ? O1 Eu1 O8 C14 -118.71(19) . . . . ? N1 Eu1 O8 C14 -8.97(18) . . . . ? N2 Eu1 O8 C14 -24.1(2) . . . . ? 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 H2W1 O3 0.819(18) 1.863(19) 2.662(2) 165(3) 3_566 O1W H1W1 O2 0.819(18) 1.844(18) 2.655(2) 170(3) 4_575 N3 H1N3 O6 0.92(3) 1.78(3) 2.702(3) 174(3) . N3 H2N3 O1 0.87(4) 2.08(4) 2.819(3) 141(3) 2_645 N3 H2N3 O1W 0.87(4) 2.56(4) 3.243(4) 136(3) 2_645 _diffrn_measured_fraction_theta_max 1.000 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 1.000 _refine_diff_density_max 0.632 _refine_diff_density_min -0.375 _refine_diff_density_rms 0.079 ####END data_4 _database_code_depnum_ccdc_archive 'CCDC 683756' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common 10 _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C14 H11 Gd N2 O13' _chemical_formula_weight 572.50 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 Orthorhombic _symmetry_space_group_name_H-M Pnma loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, -y, z+1/2' 'x+1/2, -y+1/2, -z+1/2' '-x, y+1/2, -z' '-x, -y, -z' 'x-1/2, y, -z-1/2' '-x-1/2, y-1/2, z-1/2' 'x, -y-1/2, z' _cell_length_a 21.9198(10) _cell_length_b 6.6040(3) _cell_length_c 11.3592(5) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 1644.34(13) _cell_formula_units_Z 4 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description block _exptl_crystal_colour colourless _exptl_crystal_size_max 0.14 _exptl_crystal_size_mid 0.09 _exptl_crystal_size_min 0.05 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 2.313 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1108 _exptl_absorpt_coefficient_mu 4.118 _exptl_absorpt_correction_type empirical _exptl_absorpt_correction_T_min 0.8325 _exptl_absorpt_correction_T_max 1.0000 _exptl_absorpt_process_details SADABS _exptl_special_details ; ? ; _diffrn_ambient_temperature 293(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Bruker SMART APEX CCD' _diffrn_measurement_method 'omega scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 12536 _diffrn_reflns_av_R_equivalents 0.0225 _diffrn_reflns_av_sigmaI/netI 0.0134 _diffrn_reflns_limit_h_min -26 _diffrn_reflns_limit_h_max 26 _diffrn_reflns_limit_k_min -7 _diffrn_reflns_limit_k_max 7 _diffrn_reflns_limit_l_min -13 _diffrn_reflns_limit_l_max 13 _diffrn_reflns_theta_min 1.86 _diffrn_reflns_theta_max 25.00 _reflns_number_total 1588 _reflns_number_gt 1581 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SMART' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0223P)^2^+73.6823P] 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 mixed _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 1588 _refine_ls_number_parameters 125 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0651 _refine_ls_R_factor_gt 0.0650 _refine_ls_wR_factor_ref 0.1657 _refine_ls_wR_factor_gt 0.1657 _refine_ls_goodness_of_fit_ref 1.367 _refine_ls_restrained_S_all 1.367 _refine_ls_shift/su_max 0.117 _refine_ls_shift/su_mean 0.001 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 0.13186(3) 0.2500 0.03345(7) 0.0151(3) Uani 1 2 d S . . N1 N 0.2447(6) 0.2500 0.0785(12) 0.025(4) Uani 1 2 d S . . C1 C 0.2622(8) 0.2500 0.1913(16) 0.020(4) Uiso 1 2 d S . . C2 C 0.3227(8) 0.2500 0.2248(16) 0.030(5) Uani 1 2 d S . . H2A H 0.3334 0.2500 0.3040 0.036 Uiso 1 2 calc SR . . C3 C 0.3669(10) 0.2500 0.1382(19) 0.033(5) Uiso 1 2 d S . . C4 C 0.3486(8) 0.2500 0.0198(16) 0.043(7) Uani 1 2 d S . . H4A H 0.3776 0.2500 -0.0400 0.052 Uiso 1 2 calc SR . . C5 C 0.2873(8) 0.2500 -0.0070(15) 0.027(5) Uani 1 2 d S . . C6 C 0.2639(8) 0.2500 -0.1295(16) 0.019(4) Uiso 1 2 d S . . C7 C 0.3018(8) 0.2500 -0.2266(15) 0.016(4) Uiso 1 2 d S . . H7A H 0.3439 0.2500 -0.2168 0.019 Uiso 1 2 calc SR . . C8 C 0.2768(8) 0.2500 -0.3386(15) 0.017(4) Uiso 1 2 d S . . C9 C 0.2143(8) 0.2500 -0.3491(17) 0.022(4) Uiso 1 2 d S . . H9A H 0.1962 0.2500 -0.4231 0.027 Uiso 1 2 calc SR . . C10 C 0.1784(8) 0.2500 -0.2483(14) 0.020(4) Uani 1 2 d S . . N2 N 0.2036(6) 0.2500 -0.1403(13) 0.018(3) Uiso 1 2 d S . . C11 C 0.1093(9) 0.2500 -0.2492(17) 0.026(4) Uiso 1 2 d S . . O1 O 0.0837(6) 0.2500 -0.1495(11) 0.025(3) Uiso 1 2 d S . . O2 O 0.0825(7) 0.2500 -0.3453(13) 0.038(4) Uiso 1 2 d S . . C12 C 0.3202(8) 0.2500 -0.4432(15) 0.018(4) Uiso 1 2 d S . . O3 O 0.3376(4) 0.0839(16) -0.4802(7) 0.029(2) Uani 1 1 d . . . C13 C 0.4329(9) 0.2500 0.1666(15) 0.060(10) Uani 1 2 d S . . O4 O 0.4681(7) 0.2500 0.0739(14) 0.042(4) Uiso 1 2 d S . . O5 O 0.4513(8) 0.2500 0.2675(15) 0.049(4) Uiso 1 2 d S . . C14 C 0.2102(8) 0.2500 0.2790(14) 0.019(4) Uani 1 2 d S . . O6 O 0.2220(5) 0.2500 0.3845(10) 0.026(3) Uani 1 2 d S . . O7 O 0.1563(5) 0.2500 0.2347(10) 0.021(3) Uani 1 2 d S . . O1W O 0.0421(7) 0.446(3) 0.0729(16) 0.014(4) Uiso 0.50 1 d P . . O1W' O 0.0461(7) 0.475(3) 0.1160(17) 0.015(4) Uiso 0.50 1 d P . . O2W O 0.0788(7) 0.159(2) 0.4136(14) 0.086(5) Uiso 1 1 d . . . O3W O 0.0407(7) 0.670(2) 0.2760(13) 0.016(3) Uiso 0.50 1 d P . . 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 0.0074(4) 0.0301(5) 0.0079(4) 0.000 0.0001(3) 0.000 N1 0.007(7) 0.058(12) 0.009(7) 0.000 0.001(5) 0.000 C2 0.014(9) 0.067(16) 0.010(8) 0.000 -0.001(7) 0.000 C4 0.010(8) 0.11(2) 0.010(9) 0.000 0.002(7) 0.000 C5 0.013(8) 0.058(14) 0.010(8) 0.000 0.005(7) 0.000 C10 0.029(9) 0.029(10) 0.002(7) 0.000 -0.003(7) 0.000 O3 0.027(5) 0.045(6) 0.014(4) 0.007(4) 0.005(4) 0.017(5) C13 0.020(10) 0.16(3) 0.000(8) 0.000 0.000(7) 0.000 C14 0.014(8) 0.035(11) 0.008(8) 0.000 -0.001(6) 0.000 O6 0.014(6) 0.057(10) 0.006(6) 0.000 -0.002(5) 0.000 O7 0.011(5) 0.042(8) 0.009(5) 0.000 0.000(5) 0.000 _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag Gd1 O3 2.310(10) 7_666 ? Gd1 O3 2.310(10) 2 ? Gd1 O1 2.331(13) . ? Gd1 O7 2.348(11) . ? Gd1 O1W 2.397(17) 8_565 ? Gd1 O1W 2.397(17) . ? Gd1 N2 2.523(14) . ? Gd1 N1 2.526(14) . ? Gd1 O1W' 2.572(18) 8_565 ? Gd1 O1W' 2.572(18) . ? N1 C1 1.34(2) . ? N1 C5 1.35(2) . ? C1 C2 1.38(2) . ? C1 C14 1.51(2) . ? C2 C3 1.38(3) . ? C2 H2A 0.9300 . ? C3 C4 1.40(3) . ? C3 C13 1.48(3) . ? C4 C5 1.38(3) . ? C4 H4A 0.9300 . ? C5 C6 1.48(2) . ? C6 N2 1.33(2) . ? C6 C7 1.38(2) . ? C7 C8 1.39(2) . ? C7 H7A 0.9300 . ? C8 C9 1.37(2) . ? C8 C12 1.52(2) . ? C9 C10 1.39(2) . ? C9 H9A 0.9300 . ? C10 N2 1.34(2) . ? C10 C11 1.52(3) . ? C11 O2 1.24(2) . ? C11 O1 1.26(2) . ? C12 O3 1.235(12) 8_565 ? C12 O3 1.235(12) . ? O3 Gd1 2.310(10) 2_554 ? C13 O5 1.21(2) . ? C13 O4 1.31(2) . ? C14 O6 1.23(2) . ? C14 O7 1.28(2) . ? O1W O1W' 0.53(2) . ? O2W O2W 1.21(3) 8_565 ? O3W O3W 1.05(3) 8_575 ? 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 O3 145.4(5) 7_666 2 ? O3 Gd1 O1 94.1(2) 7_666 . ? O3 Gd1 O1 94.1(2) 2 . ? O3 Gd1 O7 90.0(2) 7_666 . ? O3 Gd1 O7 90.0(2) 2 . ? O1 Gd1 O7 166.3(4) . . ? O3 Gd1 O1W 140.0(5) 7_666 8_565 ? O3 Gd1 O1W 74.7(5) 2 8_565 ? O1 Gd1 O1W 78.2(5) . 8_565 ? O7 Gd1 O1W 90.3(5) . 8_565 ? O3 Gd1 O1W 74.7(5) 7_666 . ? O3 Gd1 O1W 140.0(5) 2 . ? O1 Gd1 O1W 78.2(5) . . ? O7 Gd1 O1W 90.3(5) . . ? O1W Gd1 O1W 65.3(9) 8_565 . ? O3 Gd1 N2 76.5(2) 7_666 . ? O3 Gd1 N2 76.5(2) 2 . ? O1 Gd1 N2 65.5(4) . . ? O7 Gd1 N2 128.3(4) . . ? O1W Gd1 N2 131.1(5) 8_565 . ? O1W Gd1 N2 131.1(5) . . ? O3 Gd1 N1 74.3(2) 7_666 . ? O3 Gd1 N1 74.3(2) 2 . ? O1 Gd1 N1 128.6(4) . . ? O7 Gd1 N1 65.1(4) . . ? O1W Gd1 N1 140.0(5) 8_565 . ? O1W Gd1 N1 140.0(5) . . ? N2 Gd1 N1 63.1(5) . . ? O3 Gd1 O1W' 141.9(5) 7_666 8_565 ? O3 Gd1 O1W' 71.7(5) 2 8_565 ? O1 Gd1 O1W' 89.6(5) . 8_565 ? O7 Gd1 O1W' 79.2(5) . 8_565 ? O1W Gd1 O1W' 11.6(5) 8_565 8_565 ? O1W Gd1 O1W' 69.1(5) . 8_565 ? N2 Gd1 O1W' 137.8(4) . 8_565 ? N1 Gd1 O1W' 129.9(5) . 8_565 ? O3 Gd1 O1W' 71.7(5) 7_666 . ? O3 Gd1 O1W' 141.9(5) 2 . ? O1 Gd1 O1W' 89.6(5) . . ? O7 Gd1 O1W' 79.2(5) . . ? O1W Gd1 O1W' 69.1(5) 8_565 . ? O1W Gd1 O1W' 11.6(5) . . ? N2 Gd1 O1W' 137.8(4) . . ? N1 Gd1 O1W' 129.9(5) . . ? O1W' Gd1 O1W' 70.5(8) 8_565 . ? C1 N1 C5 119.4(15) . . ? C1 N1 Gd1 118.3(11) . . ? C5 N1 Gd1 122.2(11) . . ? N1 C1 C2 122.7(16) . . ? N1 C1 C14 114.5(15) . . ? C2 C1 C14 122.8(16) . . ? C1 C2 C3 118.5(17) . . ? C1 C2 H2A 120.8 . . ? C3 C2 H2A 120.8 . . ? C2 C3 C4 118.9(19) . . ? C2 C3 C13 122.0(18) . . ? C4 C3 C13 119.2(18) . . ? C5 C4 C3 119.3(17) . . ? C5 C4 H4A 120.3 . . ? C3 C4 H4A 120.3 . . ? N1 C5 C4 121.2(16) . . ? N1 C5 C6 115.8(15) . . ? C4 C5 C6 123.0(16) . . ? N2 C6 C7 121.7(16) . . ? N2 C6 C5 115.6(15) . . ? C7 C6 C5 122.8(16) . . ? C6 C7 C8 119.7(16) . . ? C6 C7 H7A 120.1 . . ? C8 C7 H7A 120.1 . . ? C9 C8 C7 118.2(16) . . ? C9 C8 C12 123.7(16) . . ? C7 C8 C12 118.0(15) . . ? C8 C9 C10 119.6(17) . . ? C8 C9 H9A 120.2 . . ? C10 C9 H9A 120.2 . . ? N2 C10 C9 121.3(16) . . ? N2 C10 C11 114.6(15) . . ? C9 C10 C11 124.1(16) . . ? C6 N2 C10 119.5(15) . . ? C6 N2 Gd1 123.2(12) . . ? C10 N2 Gd1 117.3(11) . . ? O2 C11 O1 125.5(18) . . ? O2 C11 C10 118.6(17) . . ? O1 C11 C10 115.9(16) . . ? C11 O1 Gd1 126.7(12) . . ? O3 C12 O3 125.4(16) 8_565 . ? O3 C12 C8 117.3(8) 8_565 . ? O3 C12 C8 117.3(8) . . ? C12 O3 Gd1 156.1(9) . 2_554 ? O5 C13 O4 124(2) . . ? O5 C13 C3 122.0(19) . . ? O4 C13 C3 113.7(17) . . ? O6 C14 O7 125.2(15) . . ? O6 C14 C1 119.1(15) . . ? O7 C14 C1 115.8(14) . . ? C14 O7 Gd1 126.2(10) . . ? O1W' O1W Gd1 103(3) . . ? O1W O1W' Gd1 65(3) . . ? 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 O3 Gd1 N1 C1 97.4(2) 7_666 . . . ? O3 Gd1 N1 C1 -97.4(2) 2 . . . ? O1 Gd1 N1 C1 180.0 . . . . ? O7 Gd1 N1 C1 0.0 . . . . ? O1W Gd1 N1 C1 -57.1(7) 8_565 . . . ? O1W Gd1 N1 C1 57.1(7) . . . . ? N2 Gd1 N1 C1 180.0 . . . . ? O1W' Gd1 N1 C1 -48.8(6) 8_565 . . . ? O1W' Gd1 N1 C1 48.8(6) . . . . ? O3 Gd1 N1 C5 -82.6(2) 7_666 . . . ? O3 Gd1 N1 C5 82.6(2) 2 . . . ? O1 Gd1 N1 C5 0.0 . . . . ? O7 Gd1 N1 C5 180.0 . . . . ? O1W Gd1 N1 C5 122.9(7) 8_565 . . . ? O1W Gd1 N1 C5 -122.9(7) . . . . ? N2 Gd1 N1 C5 0.0 . . . . ? O1W' Gd1 N1 C5 131.2(6) 8_565 . . . ? O1W' Gd1 N1 C5 -131.2(6) . . . . ? C5 N1 C1 C2 0.000(1) . . . . ? Gd1 N1 C1 C2 180.0 . . . . ? C5 N1 C1 C14 180.0 . . . . ? Gd1 N1 C1 C14 0.0 . . . . ? N1 C1 C2 C3 0.000(1) . . . . ? C14 C1 C2 C3 180.000(1) . . . . ? C1 C2 C3 C4 0.000(1) . . . . ? C1 C2 C3 C13 180.0 . . . . ? C2 C3 C4 C5 0.0 . . . . ? C13 C3 C4 C5 180.0 . . . . ? C1 N1 C5 C4 0.0 . . . . ? Gd1 N1 C5 C4 180.0 . . . . ? C1 N1 C5 C6 180.0 . . . . ? Gd1 N1 C5 C6 0.0 . . . . ? C3 C4 C5 N1 0.0 . . . . ? C3 C4 C5 C6 180.0 . . . . ? N1 C5 C6 N2 0.0 . . . . ? C4 C5 C6 N2 180.0 . . . . ? N1 C5 C6 C7 180.0 . . . . ? C4 C5 C6 C7 0.0 . . . . ? N2 C6 C7 C8 0.000(1) . . . . ? C5 C6 C7 C8 180.000(1) . . . . ? C6 C7 C8 C9 0.000(2) . . . . ? C6 C7 C8 C12 180.000(1) . . . . ? C7 C8 C9 C10 0.000(2) . . . . ? C12 C8 C9 C10 180.000(1) . . . . ? C8 C9 C10 N2 0.000(2) . . . . ? C8 C9 C10 C11 180.000(2) . . . . ? C7 C6 N2 C10 0.000(1) . . . . ? C5 C6 N2 C10 180.0 . . . . ? C7 C6 N2 Gd1 180.0 . . . . ? C5 C6 N2 Gd1 0.0 . . . . ? C9 C10 N2 C6 0.000(1) . . . . ? C11 C10 N2 C6 180.0 . . . . ? C9 C10 N2 Gd1 180.000(1) . . . . ? C11 C10 N2 Gd1 0.0 . . . . ? O3 Gd1 N2 C6 79.0(2) 7_666 . . . ? O3 Gd1 N2 C6 -79.0(2) 2 . . . ? O1 Gd1 N2 C6 180.0 . . . . ? O7 Gd1 N2 C6 0.0 . . . . ? O1W Gd1 N2 C6 -134.3(6) 8_565 . . . ? O1W Gd1 N2 C6 134.3(6) . . . . ? N1 Gd1 N2 C6 0.0 . . . . ? O1W' Gd1 N2 C6 -120.9(7) 8_565 . . . ? O1W' Gd1 N2 C6 120.9(7) . . . . ? O3 Gd1 N2 C10 -101.0(2) 7_666 . . . ? O3 Gd1 N2 C10 101.0(2) 2 . . . ? O1 Gd1 N2 C10 0.0 . . . . ? O7 Gd1 N2 C10 180.0 . . . . ? O1W Gd1 N2 C10 45.7(6) 8_565 . . . ? O1W Gd1 N2 C10 -45.7(6) . . . . ? N1 Gd1 N2 C10 180.0 . . . . ? O1W' Gd1 N2 C10 59.1(7) 8_565 . . . ? O1W' Gd1 N2 C10 -59.1(7) . . . . ? N2 C10 C11 O2 180.000(1) . . . . ? C9 C10 C11 O2 0.000(2) . . . . ? N2 C10 C11 O1 0.000(1) . . . . ? C9 C10 C11 O1 180.000(1) . . . . ? O2 C11 O1 Gd1 180.000(2) . . . . ? C10 C11 O1 Gd1 0.000(1) . . . . ? O3 Gd1 O1 C11 73.2(2) 7_666 . . . ? O3 Gd1 O1 C11 -73.2(2) 2 . . . ? O7 Gd1 O1 C11 180.000(1) . . . . ? O1W Gd1 O1 C11 -146.6(4) 8_565 . . . ? O1W Gd1 O1 C11 146.6(4) . . . . ? N2 Gd1 O1 C11 0.000(1) . . . . ? N1 Gd1 O1 C11 0.000(1) . . . . ? O1W' Gd1 O1 C11 -144.8(4) 8_565 . . . ? O1W' Gd1 O1 C11 144.8(4) . . . . ? C9 C8 C12 O3 91.8(14) . . . 8_565 ? C7 C8 C12 O3 -88.2(14) . . . 8_565 ? C9 C8 C12 O3 -91.8(14) . . . . ? C7 C8 C12 O3 88.2(14) . . . . ? O3 C12 O3 Gd1 140.0(14) 8_565 . . 2_554 ? C8 C12 O3 Gd1 -36(3) . . . 2_554 ? C2 C3 C13 O5 0.000(1) . . . . ? C4 C3 C13 O5 180.000(1) . . . . ? C2 C3 C13 O4 180.0 . . . . ? C4 C3 C13 O4 0.0 . . . . ? N1 C1 C14 O6 180.0 . . . . ? C2 C1 C14 O6 0.000(1) . . . . ? N1 C1 C14 O7 0.000(1) . . . . ? C2 C1 C14 O7 180.0 . . . . ? O6 C14 O7 Gd1 180.000(1) . . . . ? C1 C14 O7 Gd1 0.0 . . . . ? O3 Gd1 O7 C14 -72.7(2) 7_666 . . . ? O3 Gd1 O7 C14 72.7(2) 2 . . . ? O1 Gd1 O7 C14 180.000(1) . . . . ? O1W Gd1 O7 C14 147.4(4) 8_565 . . . ? O1W Gd1 O7 C14 -147.4(4) . . . . ? N2 Gd1 O7 C14 0.000(1) . . . . ? N1 Gd1 O7 C14 0.0 . . . . ? O1W' Gd1 O7 C14 144.0(4) 8_565 . . . ? O1W' Gd1 O7 C14 -144.0(4) . . . . ? O3 Gd1 O1W O1W' -73(3) 7_666 . . . ? O3 Gd1 O1W O1W' 107(3) 2 . . . ? O1 Gd1 O1W O1W' -171(3) . . . . ? O7 Gd1 O1W O1W' 16(3) . . . . ? O1W Gd1 O1W O1W' 107(3) 8_565 . . . ? N2 Gd1 O1W O1W' -129(3) . . . . ? N1 Gd1 O1W O1W' -33(4) . . . . ? O1W' Gd1 O1W O1W' 95(3) 8_565 . . . ? O3 Gd1 O1W' O1W 103(3) 7_666 . . . ? O3 Gd1 O1W' O1W -87(3) 2 . . . ? O1 Gd1 O1W' O1W 9(3) . . . . ? O7 Gd1 O1W' O1W -163(3) . . . . ? O1W Gd1 O1W' O1W -69(3) 8_565 . . . ? N2 Gd1 O1W' O1W 60(4) . . . . ? N1 Gd1 O1W' O1W 153(3) . . . . ? O1W' Gd1 O1W' O1W -81(3) 8_565 . . . ? _diffrn_measured_fraction_theta_max 1.000 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 1.000 _refine_diff_density_max 2.140 _refine_diff_density_min -2.567 _refine_diff_density_rms 0.334