data_global _journal_name_full CrystEngComm _journal_coden_Cambridge 1350 _journal_volume ? _journal_page_first ? _journal_year ? _publ_contact_author_name 'Cui, Jian-Zhong' _publ_contact_author_email cuijianzhong@tju.edu.cn _publ_section_title ; Syntheses, Structures, and Photoluminescence of Lanthanide Coordination Polymers with Pyridine-2,3,5,6-tetracarboxylic Acid ; loop_ _publ_author_name 'Ai-Hong Yang' 'Hong-Ling Gao' 'Jian-Zhong Cui' 'Bin Zhao' # Attachment '- complex 2.cif' data_r71021h _database_code_depnum_ccdc_archive 'CCDC 702817' #TrackingRef '- complex 2.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C9 H10 Ce N O12' _chemical_formula_weight 464.30 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' Ce Ce -0.2486 2.6331 '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 8.4701(17) _cell_length_b 8.9690(18) _cell_length_c 9.4258(19) _cell_angle_alpha 95.70(3) _cell_angle_beta 115.11(3) _cell_angle_gamma 95.39(3) _cell_volume 637.8(2) _cell_formula_units_Z 2 _cell_measurement_temperature 113(2) _cell_measurement_reflns_used 1379 _cell_measurement_theta_min 2.308 _cell_measurement_theta_max 27.884 _exptl_crystal_description ? _exptl_crystal_colour ? _exptl_crystal_size_max 0.08 _exptl_crystal_size_mid 0.06 _exptl_crystal_size_min 0.02 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 2.418 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 450 _exptl_absorpt_coefficient_mu 3.644 _exptl_absorpt_correction_type MULTI-SCAN _exptl_absorpt_correction_T_min 0.7592 _exptl_absorpt_correction_T_max 0.9307 _exptl_absorpt_process_details crystalclear _exptl_special_details ; ? ; _diffrn_ambient_temperature 113(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'rotating anode' _diffrn_radiation_monochromator confocal _diffrn_measurement_device_type 'rigaku saturn' _diffrn_measurement_method '\w scans' _diffrn_detector_area_resol_mean 7.31 _diffrn_standards_number 0 _diffrn_standards_interval_count 0 _diffrn_standards_interval_time 0 _diffrn_standards_decay_% 0 _diffrn_reflns_number 5969 _diffrn_reflns_av_R_equivalents 0.0409 _diffrn_reflns_av_sigmaI/netI 0.0621 _diffrn_reflns_limit_h_min -11 _diffrn_reflns_limit_h_max 11 _diffrn_reflns_limit_k_min -11 _diffrn_reflns_limit_k_max 11 _diffrn_reflns_limit_l_min -12 _diffrn_reflns_limit_l_max 12 _diffrn_reflns_theta_min 2.31 _diffrn_reflns_theta_max 27.85 _reflns_number_total 2942 _reflns_number_gt 2597 _reflns_threshold_expression >2sigma(I) _computing_data_collection crystalclear _computing_cell_refinement crystalclear _computing_data_reduction crystalclear _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^)+(0.0102P)^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 2942 _refine_ls_number_parameters 209 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0280 _refine_ls_R_factor_gt 0.0243 _refine_ls_wR_factor_ref 0.0546 _refine_ls_wR_factor_gt 0.0536 _refine_ls_goodness_of_fit_ref 0.988 _refine_ls_restrained_S_all 0.988 _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 Ce1 Ce 0.67854(2) 0.30468(2) 0.30597(2) 0.00730(6) Uani 1 1 d . . . O1 O 0.4110(3) 0.0985(3) 0.1559(2) 0.0098(5) Uani 1 1 d . . . O2 O 0.1627(3) -0.0679(3) 0.0308(2) 0.0123(5) Uani 1 1 d . . . H2A H 0.1804 -0.0563 -0.0489 0.018 Uiso 1 1 calc R . . O3 O 0.3771(4) -0.2466(3) 0.2362(3) 0.0240(6) Uani 1 1 d . . . O4 O 0.3620(3) -0.3325(3) 0.4461(3) 0.0130(5) Uani 1 1 d . . . O5 O 0.2214(3) -0.0759(3) 0.7884(2) 0.0095(5) Uani 1 1 d . . . O6 O 0.1838(4) 0.1673(3) 0.7931(3) 0.0209(6) Uani 1 1 d . . . O7 O -0.0191(3) 0.3236(3) 0.5161(3) 0.0109(5) Uani 1 1 d . . . O8 O 0.2634(3) 0.4230(3) 0.6070(3) 0.0148(5) Uani 1 1 d . . . O9 O 0.4012(3) 0.4158(3) 0.2432(3) 0.0168(6) Uani 1 1 d . . . H9A H 0.3930 0.4847 0.3074 0.025 Uiso 1 1 d R . . H9B H 0.3124 0.3973 0.1530 0.025 Uiso 1 1 d R . . O10 O 0.9234(3) 0.4262(3) 0.2274(3) 0.0173(6) Uani 1 1 d . . . H10A H 0.9019 0.4701 0.1466 0.026 Uiso 1 1 d R . . H10B H 0.9782 0.4904 0.3114 0.026 Uiso 1 1 d R . . O11 O 0.5493(3) 0.3397(3) 0.0121(3) 0.0250(7) Uani 1 1 d . . . H11A H 0.5995 0.3438 -0.0490 0.038 Uiso 1 1 d R . . H11B H 0.4517 0.2802 -0.0291 0.038 Uiso 1 1 d R . . N1 N 0.2752(3) -0.0757(3) 0.5324(3) 0.0076(6) Uani 1 1 d . . . C1 C 0.3480(4) -0.2344(4) 0.3554(4) 0.0118(7) Uani 1 1 d . . . C2 C 0.2912(4) -0.0882(4) 0.3967(4) 0.0078(7) Uani 1 1 d . . . C3 C 0.2553(4) 0.0244(4) 0.3024(4) 0.0079(7) Uani 1 1 d . . . C4 C 0.2043(4) 0.1539(4) 0.3513(4) 0.0092(7) Uani 1 1 d . . . H4 H 0.1811 0.2332 0.2887 0.011 Uiso 1 1 calc R . . C5 C 0.1869(4) 0.1684(4) 0.4929(4) 0.0069(7) Uani 1 1 d . . . C6 C 0.2239(4) 0.0491(4) 0.5790(4) 0.0075(7) Uani 1 1 d . . . C7 C 0.2085(4) 0.0505(4) 0.7334(4) 0.0087(7) Uani 1 1 d . . . C8 C 0.2856(4) 0.0183(4) 0.1554(4) 0.0095(7) Uani 1 1 d . . . C9 C 0.1386(4) 0.3154(4) 0.5453(3) 0.0076(7) Uani 1 1 d . . . O12 O 0.9142(3) 0.6515(3) 0.0263(3) 0.0193(6) Uani 1 1 d . . . H12A H 0.8765 0.7106 0.0772 0.029 Uiso 1 1 d R . . H12B H 1.0184 0.6873 0.0437 0.029 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 Ce1 0.00787(10) 0.00597(10) 0.00743(10) 0.00065(7) 0.00297(7) 0.00045(7) O1 0.0100(12) 0.0096(12) 0.0105(11) -0.0011(10) 0.0067(10) -0.0037(10) O2 0.0133(13) 0.0181(14) 0.0050(11) -0.0008(10) 0.0054(10) -0.0040(10) O3 0.0411(17) 0.0239(16) 0.0199(14) 0.0065(12) 0.0225(13) 0.0165(14) O4 0.0183(13) 0.0104(13) 0.0146(12) 0.0032(10) 0.0106(11) 0.0040(10) O5 0.0139(12) 0.0087(12) 0.0084(11) 0.0027(9) 0.0070(10) 0.0013(10) O6 0.0435(17) 0.0137(14) 0.0167(13) 0.0044(11) 0.0217(13) 0.0127(13) O7 0.0083(12) 0.0101(13) 0.0112(12) -0.0008(10) 0.0021(10) -0.0007(10) O8 0.0097(12) 0.0092(13) 0.0236(14) -0.0036(11) 0.0075(11) -0.0019(10) O9 0.0105(12) 0.0146(14) 0.0184(13) -0.0048(11) 0.0013(10) 0.0021(10) O10 0.0201(14) 0.0174(14) 0.0145(13) 0.0013(11) 0.0089(11) -0.0020(11) O11 0.0153(14) 0.048(2) 0.0137(13) 0.0053(13) 0.0082(11) 0.0023(13) N1 0.0046(13) 0.0100(15) 0.0062(13) -0.0013(11) 0.0019(11) -0.0029(11) C1 0.0129(17) 0.0124(18) 0.0112(16) 0.0001(14) 0.0064(14) 0.0029(14) C2 0.0057(15) 0.0082(17) 0.0091(16) -0.0006(13) 0.0040(13) -0.0023(13) C3 0.0070(15) 0.0112(17) 0.0044(15) 0.0002(13) 0.0025(13) -0.0020(13) C4 0.0094(16) 0.0085(17) 0.0080(15) 0.0024(13) 0.0023(13) -0.0003(13) C5 0.0061(15) 0.0079(17) 0.0053(15) 0.0000(13) 0.0021(12) -0.0022(13) C6 0.0067(15) 0.0096(17) 0.0068(15) 0.0005(13) 0.0041(12) -0.0008(13) C7 0.0089(16) 0.0108(18) 0.0078(15) 0.0011(13) 0.0054(13) -0.0007(13) C8 0.0118(17) 0.0087(17) 0.0094(16) 0.0025(13) 0.0050(13) 0.0062(14) C9 0.0139(17) 0.0063(16) 0.0048(15) 0.0030(13) 0.0053(13) 0.0030(13) O12 0.0159(13) 0.0235(16) 0.0189(13) -0.0032(11) 0.0096(11) 0.0029(11) _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 Ce1 O8 2.432(2) 2_666 ? Ce1 O7 2.461(2) 1_655 ? Ce1 O4 2.494(2) 2_656 ? Ce1 O9 2.497(2) . ? Ce1 O5 2.515(2) 2_656 ? Ce1 O1 2.555(3) . ? Ce1 O11 2.576(2) . ? Ce1 N1 2.638(3) 2_656 ? Ce1 O10 2.661(2) . ? O1 C8 1.223(4) . ? O2 C8 1.300(4) . ? O2 H2A 0.8400 . ? O3 C1 1.245(4) . ? O4 C1 1.266(4) . ? O4 Ce1 2.494(2) 2_656 ? O5 C7 1.288(4) . ? O5 Ce1 2.515(2) 2_656 ? O6 C7 1.217(4) . ? O7 C9 1.256(4) . ? O7 Ce1 2.461(2) 1_455 ? O8 C9 1.250(4) . ? O8 Ce1 2.432(2) 2_666 ? O9 H9A 0.8501 . ? O9 H9B 0.8500 . ? O10 H10A 0.8500 . ? O10 H10B 0.8500 . ? O11 H11A 0.8501 . ? O11 H11B 0.8501 . ? N1 C2 1.338(4) . ? N1 C6 1.338(4) . ? N1 Ce1 2.638(3) 2_656 ? C1 C2 1.510(4) . ? C2 C3 1.382(4) . ? C3 C4 1.380(4) . ? C3 C8 1.510(4) . ? C4 C5 1.399(4) . ? C4 H4 0.9500 . ? C5 C6 1.387(4) . ? C5 C9 1.514(4) . ? C6 C7 1.514(4) . ? O12 H12A 0.8503 . ? O12 H12B 0.8499 . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag O8 Ce1 O7 81.30(8) 2_666 1_655 ? O8 Ce1 O4 75.98(8) 2_666 2_656 ? O7 Ce1 O4 76.83(8) 1_655 2_656 ? O8 Ce1 O9 67.85(8) 2_666 . ? O7 Ce1 O9 141.17(8) 1_655 . ? O4 Ce1 O9 73.34(8) 2_656 . ? O8 Ce1 O5 147.36(8) 2_666 2_656 ? O7 Ce1 O5 78.70(8) 1_655 2_656 ? O4 Ce1 O5 123.26(7) 2_656 2_656 ? O9 Ce1 O5 139.11(8) . 2_656 ? O8 Ce1 O1 137.87(8) 2_666 . ? O7 Ce1 O1 137.14(8) 1_655 . ? O4 Ce1 O1 94.41(8) 2_656 . ? O9 Ce1 O1 70.08(8) . . ? O5 Ce1 O1 71.46(7) 2_656 . ? O8 Ce1 O11 91.83(9) 2_666 . ? O7 Ce1 O11 133.71(8) 1_655 . ? O4 Ce1 O11 145.66(8) 2_656 . ? O9 Ce1 O11 72.33(8) . . ? O5 Ce1 O11 83.78(8) 2_656 . ? O1 Ce1 O11 73.14(8) . . ? O8 Ce1 N1 131.20(8) 2_666 2_656 ? O7 Ce1 N1 66.84(8) 1_655 2_656 ? O4 Ce1 N1 61.80(8) 2_656 2_656 ? O9 Ce1 N1 117.22(8) . 2_656 ? O5 Ce1 N1 61.56(8) 2_656 2_656 ? O1 Ce1 N1 72.06(8) . 2_656 ? O11 Ce1 N1 136.91(9) . 2_656 ? O8 Ce1 O10 71.33(8) 2_666 . ? O7 Ce1 O10 66.67(8) 1_655 . ? O4 Ce1 O10 133.69(8) 2_656 . ? O9 Ce1 O10 120.59(8) . . ? O5 Ce1 O10 77.14(7) 2_656 . ? O1 Ce1 O10 131.74(7) . . ? O11 Ce1 O10 67.77(8) . . ? N1 Ce1 O10 122.08(8) 2_656 . ? C8 O1 Ce1 148.4(2) . . ? C8 O2 H2A 109.5 . . ? C1 O4 Ce1 126.9(2) . 2_656 ? C7 O5 Ce1 126.5(2) . 2_656 ? C9 O7 Ce1 145.2(2) . 1_455 ? C9 O8 Ce1 140.9(2) . 2_666 ? Ce1 O9 H9A 122.0 . . ? Ce1 O9 H9B 123.7 . . ? H9A O9 H9B 113.8 . . ? Ce1 O10 H10A 124.5 . . ? Ce1 O10 H10B 96.3 . . ? H10A O10 H10B 109.8 . . ? Ce1 O11 H11A 129.5 . . ? Ce1 O11 H11B 103.1 . . ? H11A O11 H11B 113.2 . . ? C2 N1 C6 119.4(3) . . ? C2 N1 Ce1 119.8(2) . 2_656 ? C6 N1 Ce1 120.6(2) . 2_656 ? O3 C1 O4 126.4(3) . . ? O3 C1 C2 117.0(3) . . ? O4 C1 C2 116.6(3) . . ? N1 C2 C3 121.7(3) . . ? N1 C2 C1 114.7(3) . . ? C3 C2 C1 123.6(3) . . ? C4 C3 C2 118.9(3) . . ? C4 C3 C8 118.2(3) . . ? C2 C3 C8 122.6(3) . . ? C3 C4 C5 120.0(3) . . ? C3 C4 H4 120.0 . . ? C5 C4 H4 120.0 . . ? C6 C5 C4 117.1(3) . . ? C6 C5 C9 124.7(3) . . ? C4 C5 C9 118.1(3) . . ? N1 C6 C5 122.9(3) . . ? N1 C6 C7 114.9(3) . . ? C5 C6 C7 122.2(3) . . ? O6 C7 O5 126.0(3) . . ? O6 C7 C6 118.6(3) . . ? O5 C7 C6 115.4(3) . . ? O1 C8 O2 124.7(3) . . ? O1 C8 C3 120.5(3) . . ? O2 C8 C3 114.6(3) . . ? O8 C9 O7 125.5(3) . . ? O8 C9 C5 114.7(3) . . ? O7 C9 C5 119.7(3) . . ? H12A O12 H12B 110.1 . . ? 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 O8 Ce1 O1 C8 -73.2(4) 2_666 . . . ? O7 Ce1 O1 C8 76.1(4) 1_655 . . . ? O4 Ce1 O1 C8 0.7(4) 2_656 . . . ? O9 Ce1 O1 C8 -69.8(4) . . . . ? O5 Ce1 O1 C8 124.4(4) 2_656 . . . ? O11 Ce1 O1 C8 -146.6(4) . . . . ? N1 Ce1 O1 C8 59.2(4) 2_656 . . . ? O10 Ce1 O1 C8 176.5(4) . . . . ? Ce1 O4 C1 O3 176.1(3) 2_656 . . . ? Ce1 O4 C1 C2 -3.6(4) 2_656 . . . ? C6 N1 C2 C3 -0.3(5) . . . . ? Ce1 N1 C2 C3 175.1(2) 2_656 . . . ? C6 N1 C2 C1 -179.4(3) . . . . ? Ce1 N1 C2 C1 -4.0(3) 2_656 . . . ? O3 C1 C2 N1 -174.9(3) . . . . ? O4 C1 C2 N1 4.8(4) . . . . ? O3 C1 C2 C3 6.0(5) . . . . ? O4 C1 C2 C3 -174.3(3) . . . . ? N1 C2 C3 C4 1.0(5) . . . . ? C1 C2 C3 C4 -180.0(3) . . . . ? N1 C2 C3 C8 175.2(3) . . . . ? C1 C2 C3 C8 -5.7(5) . . . . ? C2 C3 C4 C5 -1.0(5) . . . . ? C8 C3 C4 C5 -175.5(3) . . . . ? C3 C4 C5 C6 0.4(4) . . . . ? C3 C4 C5 C9 177.3(3) . . . . ? C2 N1 C6 C5 -0.4(5) . . . . ? Ce1 N1 C6 C5 -175.8(2) 2_656 . . . ? C2 N1 C6 C7 179.4(3) . . . . ? Ce1 N1 C6 C7 4.0(4) 2_656 . . . ? C4 C5 C6 N1 0.3(5) . . . . ? C9 C5 C6 N1 -176.3(3) . . . . ? C4 C5 C6 C7 -179.5(3) . . . . ? C9 C5 C6 C7 3.9(5) . . . . ? Ce1 O5 C7 O6 -169.1(3) 2_656 . . . ? Ce1 O5 C7 C6 11.7(4) 2_656 . . . ? N1 C6 C7 O6 171.1(3) . . . . ? C5 C6 C7 O6 -9.1(5) . . . . ? N1 C6 C7 O5 -9.6(4) . . . . ? C5 C6 C7 O5 170.2(3) . . . . ? Ce1 O1 C8 O2 171.6(2) . . . . ? Ce1 O1 C8 C3 -2.9(6) . . . . ? C4 C3 C8 O1 69.1(4) . . . . ? C2 C3 C8 O1 -105.2(4) . . . . ? C4 C3 C8 O2 -105.9(4) . . . . ? C2 C3 C8 O2 79.8(4) . . . . ? Ce1 O8 C9 O7 -5.7(5) 2_666 . . . ? Ce1 O8 C9 C5 169.6(2) 2_666 . . . ? Ce1 O7 C9 O8 114.2(4) 1_455 . . . ? Ce1 O7 C9 C5 -60.9(5) 1_455 . . . ? C6 C5 C9 O8 98.8(4) . . . . ? C4 C5 C9 O8 -77.8(4) . . . . ? C6 C5 C9 O7 -85.6(4) . . . . ? C4 C5 C9 O7 97.7(4) . . . . ? _diffrn_measured_fraction_theta_max 0.971 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 0.988 _refine_diff_density_max 1.006 _refine_diff_density_min -1.167 _refine_diff_density_rms 0.141 # Attachment '- complex 6.cif' data_r90724h _database_code_depnum_ccdc_archive 'CCDC 748310' #TrackingRef '- complex 6.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C9 H9 K N O12 Sm' _chemical_formula_weight 512.62 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' K K 0.2009 0.2494 '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 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 6.7590(14) _cell_length_b 13.978(3) _cell_length_c 15.517(4) _cell_angle_alpha 90.00 _cell_angle_beta 113.30(3) _cell_angle_gamma 90.00 _cell_volume 1346.4(5) _cell_formula_units_Z 4 _cell_measurement_temperature 113(2) _cell_measurement_reflns_used 3690 _cell_measurement_theta_min 2.041 _cell_measurement_theta_max 27.876 _exptl_crystal_description ? _exptl_crystal_colour ? _exptl_crystal_size_max 0.10 _exptl_crystal_size_mid 0.04 _exptl_crystal_size_min 0.04 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 2.529 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 988 _exptl_absorpt_coefficient_mu 4.744 _exptl_absorpt_correction_type MULTI-SCAN _exptl_absorpt_correction_T_min 0.6484 _exptl_absorpt_correction_T_max 0.8329 _exptl_absorpt_process_details crystalclear _exptl_special_details ; ? ; _diffrn_ambient_temperature 113(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'rotating anode' _diffrn_radiation_monochromator confocal _diffrn_measurement_device_type 'rigaku saturn CCD area detector' _diffrn_measurement_method '\w and \f scans' _diffrn_detector_area_resol_mean 7.31 _diffrn_standards_number 0 _diffrn_standards_interval_count 0 _diffrn_standards_interval_time 0 _diffrn_standards_decay_% 0 _diffrn_reflns_number 10183 _diffrn_reflns_av_R_equivalents 0.0723 _diffrn_reflns_av_sigmaI/netI 0.0693 _diffrn_reflns_limit_h_min -8 _diffrn_reflns_limit_h_max 8 _diffrn_reflns_limit_k_min -17 _diffrn_reflns_limit_k_max 11 _diffrn_reflns_limit_l_min -19 _diffrn_reflns_limit_l_max 19 _diffrn_reflns_theta_min 2.04 _diffrn_reflns_theta_max 26.00 _reflns_number_total 2647 _reflns_number_gt 2264 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'crystalclear(Rigaku/MSC Inc., 2005)' _computing_cell_refinement crystalclear _computing_data_reduction crystalclear _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^)+(0.0545P)^2^+16.0140P] 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 SHELXL _refine_ls_extinction_coef 0.0005(4) _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_number_reflns 2647 _refine_ls_number_parameters 218 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0688 _refine_ls_R_factor_gt 0.0587 _refine_ls_wR_factor_ref 0.1428 _refine_ls_wR_factor_gt 0.1377 _refine_ls_goodness_of_fit_ref 1.130 _refine_ls_restrained_S_all 1.130 _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 0.17380(7) 0.74409(3) -0.06540(3) 0.0109(2) Uani 1 1 d . . . K1 K 0.5519(4) 0.69055(16) 0.25824(16) 0.0223(5) Uani 1 1 d . . . O1 O 0.3252(10) 0.6489(4) 0.0731(5) 0.0137(14) Uani 1 1 d . . . O2 O 0.4163(13) 0.5112(4) 0.1489(5) 0.0233(17) Uani 1 1 d . . . O3 O 0.5127(11) 0.3161(5) 0.0830(5) 0.0176(14) Uani 1 1 d . . . O4 O 0.1886(11) 0.2993(5) 0.0827(5) 0.0175(14) Uani 1 1 d . . . O5 O -0.2497(11) 0.3528(5) -0.3197(5) 0.0171(14) Uani 1 1 d . . . O6 O 0.0417(11) 0.3862(4) -0.3413(5) 0.0159(14) Uani 1 1 d . . . O7 O -0.2025(12) 0.5769(5) -0.3288(5) 0.0260(17) Uani 1 1 d . . . O8 O -0.0260(12) 0.6911(5) -0.2263(5) 0.0215(16) Uani 1 1 d . . . N1 N 0.1377(13) 0.5648(5) -0.0899(6) 0.0125(16) Uani 1 1 d . . . C1 C 0.3328(13) 0.5589(6) 0.0760(6) 0.0094(18) Uani 1 1 d . . . C2 C 0.2310(14) 0.5055(6) -0.0168(6) 0.0098(17) Uani 1 1 d . . . C3 C 0.2231(15) 0.4068(6) -0.0284(7) 0.0121(18) Uani 1 1 d . . . C4 C 0.1231(15) 0.3702(6) -0.1191(7) 0.0134(19) Uani 1 1 d . . . H4 H 0.1172 0.3029 -0.1288 0.016 Uiso 1 1 calc R . . C5 C 0.0323(16) 0.4312(6) -0.1951(7) 0.0137(19) Uani 1 1 d . . . C6 C 0.0395(14) 0.5302(6) -0.1770(6) 0.0121(18) Uani 1 1 d . . . C7 C -0.0722(16) 0.6051(7) -0.2507(7) 0.016(2) Uani 1 1 d . . . C8 C 0.3171(14) 0.3357(6) 0.0527(6) 0.0107(18) Uani 1 1 d . . . C9 C -0.0706(16) 0.3899(6) -0.2922(7) 0.0137(19) Uani 1 1 d . . . O9 O 0.0762(11) 0.8319(5) 0.0501(5) 0.0218(16) Uani 1 1 d . . . H9B H -0.0129 0.7992 0.0641 0.033 Uiso 1 1 d R . . H9C H 0.0165 0.8847 0.0266 0.033 Uiso 1 1 d R . . O10 O 0.4654(12) 0.8619(5) 0.0160(5) 0.0242(16) Uani 1 1 d . . . H10A H 0.5032 0.8772 0.0733 0.036 Uiso 1 1 d R . . H10B H 0.5788 0.8574 0.0051 0.036 Uiso 1 1 d R . . O11 O 0.7371(12) 0.5442(5) 0.4470(6) 0.0253(17) Uani 1 1 d . . . H11A H 0.6324 0.5127 0.4079 0.038 Uiso 1 1 d R . . H11B H 0.7627 0.5220 0.5013 0.038 Uiso 1 1 d R . . O12 O 0.3998(15) 0.8769(6) 0.2150(6) 0.042(2) Uani 1 1 d . . . H12A H 0.2697 0.8646 0.1797 0.063 Uiso 1 1 d R . . H12B H 0.3990 0.9183 0.2550 0.063 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 0.0116(3) 0.0076(3) 0.0128(3) 0.00040(16) 0.0040(2) 0.00031(16) K1 0.0185(12) 0.0254(12) 0.0203(12) -0.0052(8) 0.0049(9) -0.0029(8) O1 0.010(4) 0.010(3) 0.022(4) 0.001(2) 0.007(3) 0.002(2) O2 0.039(5) 0.008(3) 0.018(4) -0.001(3) 0.006(3) 0.002(3) O3 0.005(3) 0.025(4) 0.022(4) 0.007(3) 0.006(3) 0.006(3) O4 0.008(3) 0.020(4) 0.027(4) 0.003(3) 0.009(3) -0.003(3) O5 0.004(3) 0.023(4) 0.023(4) -0.007(3) 0.005(3) -0.001(3) O6 0.011(4) 0.019(3) 0.020(4) 0.001(3) 0.008(3) 0.001(2) O7 0.030(5) 0.021(4) 0.017(4) 0.000(3) -0.002(3) 0.006(3) O8 0.029(4) 0.014(3) 0.017(4) 0.003(3) 0.003(3) -0.001(3) N1 0.013(4) 0.007(4) 0.017(4) -0.001(3) 0.006(3) 0.001(3) C1 0.005(5) 0.008(4) 0.017(5) 0.003(3) 0.007(4) 0.002(3) C2 0.006(4) 0.010(4) 0.014(5) 0.003(3) 0.005(4) -0.001(3) C3 0.011(5) 0.011(4) 0.017(5) -0.001(3) 0.008(4) 0.000(3) C4 0.011(5) 0.012(4) 0.020(5) -0.003(3) 0.008(4) -0.002(3) C5 0.017(5) 0.010(4) 0.015(5) -0.001(3) 0.006(4) 0.003(3) C6 0.003(4) 0.018(5) 0.014(5) 0.001(3) 0.002(4) -0.001(3) C7 0.013(5) 0.018(5) 0.016(5) -0.003(4) 0.005(4) 0.002(4) C8 0.004(4) 0.008(4) 0.017(5) -0.004(3) 0.001(4) -0.003(3) C9 0.014(5) 0.010(4) 0.022(5) 0.002(3) 0.012(4) 0.004(3) O9 0.011(4) 0.023(4) 0.032(4) -0.005(3) 0.009(3) 0.001(3) O10 0.017(4) 0.038(4) 0.020(4) -0.010(3) 0.010(3) -0.012(3) O11 0.024(4) 0.015(4) 0.039(5) -0.004(3) 0.016(4) -0.006(3) O12 0.042(6) 0.035(5) 0.030(5) -0.017(4) -0.007(4) 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 Sm1 O1 2.386(6) . ? Sm1 O3 2.394(6) 3_665 ? Sm1 O4 2.433(6) 3_565 ? Sm1 O8 2.437(7) . ? Sm1 O9 2.469(7) . ? Sm1 O10 2.494(7) . ? Sm1 N1 2.532(7) . ? Sm1 O5 2.545(6) 2_554 ? Sm1 O6 2.549(7) 2_554 ? Sm1 C9 2.881(9) 2_554 ? Sm1 K1 4.110(3) 4_475 ? Sm1 K1 4.515(3) 4_575 ? K1 O5 2.644(7) 3_565 ? K1 O1 2.732(7) . ? K1 O6 2.749(7) 3_665 ? K1 O12 2.783(8) . ? K1 O4 2.838(7) 2_655 ? K1 O2 2.962(7) . ? K1 O3 3.193(7) 2_655 ? K1 C1 3.204(9) . ? K1 O8 3.224(8) 4_676 ? K1 O11 3.381(8) . ? K1 C8 3.385(9) 2_655 ? K1 C9 3.517(9) 3_665 ? K1 H12A 3.0335 . ? O1 C1 1.259(11) . ? O2 C1 1.240(11) . ? O3 C8 1.246(11) . ? O3 Sm1 2.394(6) 3_665 ? O3 K1 3.193(7) 2_645 ? O4 C8 1.245(11) . ? O4 Sm1 2.433(6) 3_565 ? O4 K1 2.838(7) 2_645 ? O5 C9 1.227(12) . ? O5 Sm1 2.545(6) 2_544 ? O5 K1 2.644(7) 3_565 ? O6 C9 1.272(11) . ? O6 Sm1 2.549(7) 2_544 ? O6 K1 2.749(7) 3_665 ? O7 C7 1.248(12) . ? O8 C7 1.262(11) . ? O8 K1 3.224(8) 4_475 ? N1 C6 1.337(12) . ? N1 C2 1.344(11) . ? C1 C2 1.523(12) . ? C2 C3 1.390(12) . ? C3 C4 1.395(13) . ? C3 C8 1.530(12) . ? C4 C5 1.387(13) . ? C4 H4 0.9500 . ? C5 C6 1.409(12) . ? C5 C9 1.504(13) . ? C6 C7 1.513(12) . ? C8 K1 3.385(9) 2_645 ? C9 Sm1 2.881(9) 2_544 ? C9 K1 3.517(9) 3_665 ? O9 H9B 0.8501 . ? O9 H9C 0.8500 . ? O10 H10A 0.8500 . ? O10 H10B 0.8500 . ? O11 H11A 0.8501 . ? O11 H11B 0.8498 . ? O12 H12A 0.8500 . ? O12 H12B 0.8500 . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag O1 Sm1 O3 79.8(2) . 3_665 ? O1 Sm1 O4 90.8(2) . 3_565 ? O3 Sm1 O4 142.9(2) 3_665 3_565 ? O1 Sm1 O8 128.3(2) . . ? O3 Sm1 O8 86.2(2) 3_665 . ? O4 Sm1 O8 71.7(2) 3_565 . ? O1 Sm1 O9 76.5(2) . . ? O3 Sm1 O9 139.5(2) 3_665 . ? O4 Sm1 O9 70.0(2) 3_565 . ? O8 Sm1 O9 134.1(2) . . ? O1 Sm1 O10 86.6(2) . . ? O3 Sm1 O10 74.5(2) 3_665 . ? O4 Sm1 O10 141.2(2) 3_565 . ? O8 Sm1 O10 136.6(2) . . ? O9 Sm1 O10 71.9(2) . . ? O1 Sm1 N1 64.2(2) . . ? O3 Sm1 N1 70.8(2) 3_665 . ? O4 Sm1 N1 72.8(2) 3_565 . ? O8 Sm1 N1 64.1(2) . . ? O9 Sm1 N1 124.3(2) . . ? O10 Sm1 N1 137.7(3) . . ? O1 Sm1 O5 146.1(2) . 2_554 ? O3 Sm1 O5 72.4(2) 3_665 2_554 ? O4 Sm1 O5 123.0(2) 3_565 2_554 ? O8 Sm1 O5 69.4(2) . 2_554 ? O9 Sm1 O5 113.4(2) . 2_554 ? O10 Sm1 O5 67.8(2) . 2_554 ? N1 Sm1 O5 121.3(2) . 2_554 ? O1 Sm1 O6 153.0(2) . 2_554 ? O3 Sm1 O6 122.8(2) 3_665 2_554 ? O4 Sm1 O6 78.9(2) 3_565 2_554 ? O8 Sm1 O6 72.2(2) . 2_554 ? O9 Sm1 O6 76.6(2) . 2_554 ? O10 Sm1 O6 86.1(2) . 2_554 ? N1 Sm1 O6 133.4(2) . 2_554 ? O5 Sm1 O6 50.6(2) 2_554 2_554 ? O1 Sm1 C9 166.5(2) . 2_554 ? O3 Sm1 C9 96.8(2) 3_665 2_554 ? O4 Sm1 C9 99.4(2) 3_565 2_554 ? O8 Sm1 C9 64.0(2) . 2_554 ? O9 Sm1 C9 98.7(2) . 2_554 ? O10 Sm1 C9 79.9(3) . 2_554 ? N1 Sm1 C9 127.2(3) . 2_554 ? O5 Sm1 C9 25.2(2) 2_554 2_554 ? O6 Sm1 C9 26.2(2) 2_554 2_554 ? O1 Sm1 K1 133.22(15) . 4_475 ? O3 Sm1 K1 136.10(17) 3_665 4_475 ? O4 Sm1 K1 42.45(16) 3_565 4_475 ? O8 Sm1 K1 51.62(18) . 4_475 ? O9 Sm1 K1 82.89(17) . 4_475 ? O10 Sm1 K1 125.85(18) . 4_475 ? N1 Sm1 K1 96.18(18) . 4_475 ? O5 Sm1 K1 80.63(15) 2_554 4_475 ? O6 Sm1 K1 40.92(15) 2_554 4_475 ? C9 Sm1 K1 57.22(19) 2_554 4_475 ? O1 Sm1 K1 120.97(15) . 4_575 ? O3 Sm1 K1 42.55(16) 3_665 4_575 ? O4 Sm1 K1 140.37(17) 3_565 4_575 ? O8 Sm1 K1 69.99(18) . 4_575 ? O9 Sm1 K1 135.85(17) . 4_575 ? O10 Sm1 K1 69.51(16) . 4_575 ? N1 Sm1 K1 98.80(17) . 4_575 ? O5 Sm1 K1 30.15(15) 2_554 4_575 ? O6 Sm1 K1 80.30(15) 2_554 4_575 ? C9 Sm1 K1 54.24(18) 2_554 4_575 ? K1 Sm1 K1 103.09(5) 4_475 4_575 ? O5 K1 O1 98.0(2) 3_565 . ? O5 K1 O6 120.8(2) 3_565 3_665 ? O1 K1 O6 116.8(2) . 3_665 ? O5 K1 O12 92.1(3) 3_565 . ? O1 K1 O12 86.9(2) . . ? O6 K1 O12 133.1(3) 3_665 . ? O5 K1 O4 96.2(2) 3_565 2_655 ? O1 K1 O4 157.8(2) . 2_655 ? O6 K1 O4 69.0(2) 3_665 2_655 ? O12 K1 O4 75.6(2) . 2_655 ? O5 K1 O2 84.5(2) 3_565 . ? O1 K1 O2 45.51(19) . . ? O6 K1 O2 87.9(2) 3_665 . ? O12 K1 O2 130.8(2) . . ? O4 K1 O2 153.7(2) 2_655 . ? O5 K1 O3 59.12(19) 3_565 2_655 ? O1 K1 O3 137.6(2) . 2_655 ? O6 K1 O3 105.6(2) 3_665 2_655 ? O12 K1 O3 61.4(2) . 2_655 ? O4 K1 O3 42.30(18) 2_655 2_655 ? O2 K1 O3 143.3(2) . 2_655 ? O5 K1 C1 91.9(2) 3_565 . ? O1 K1 C1 22.8(2) . . ? O6 K1 C1 102.5(2) 3_665 . ? O12 K1 C1 109.1(2) . . ? O4 K1 C1 170.5(2) 2_655 . ? O2 K1 C1 22.8(2) . . ? O3 K1 C1 147.2(2) 2_655 . ? O5 K1 O8 151.4(2) 3_565 4_676 ? O1 K1 O8 107.43(19) . 4_676 ? O6 K1 O8 58.33(19) 3_665 4_676 ? O12 K1 O8 76.7(2) . 4_676 ? O4 K1 O8 55.69(19) 2_655 4_676 ? O2 K1 O8 122.8(2) . 4_676 ? O3 K1 O8 92.72(18) 2_655 4_676 ? C1 K1 O8 116.6(2) . 4_676 ? O5 K1 O11 67.9(2) 3_565 . ? O1 K1 O11 130.06(19) . . ? O6 K1 O11 53.02(19) 3_665 . ? O12 K1 O11 138.6(2) . . ? O4 K1 O11 71.39(19) 2_655 . ? O2 K1 O11 84.75(18) . . ? O3 K1 O11 77.36(18) 2_655 . ? C1 K1 O11 107.5(2) . . ? O8 K1 O11 103.45(19) 4_676 . ? O5 K1 C8 78.4(2) 3_565 2_655 ? O1 K1 C8 152.3(2) . 2_655 ? O6 K1 C8 87.6(2) 3_665 2_655 ? O12 K1 C8 66.0(2) . 2_655 ? O4 K1 C8 20.80(19) 2_655 2_655 ? O2 K1 C8 156.9(2) . 2_655 ? O3 K1 C8 21.58(18) 2_655 2_655 ? C1 K1 C8 168.7(2) . 2_655 ? O8 K1 C8 72.99(19) 4_676 2_655 ? O11 K1 C8 74.44(19) . 2_655 ? O5 K1 C9 137.6(2) 3_565 3_665 ? O1 K1 C9 101.6(2) . 3_665 ? O6 K1 C9 18.8(2) 3_665 3_665 ? O12 K1 C9 125.9(3) . 3_665 ? O4 K1 C9 78.7(2) 2_655 3_665 ? O2 K1 C9 83.1(2) . 3_665 ? O3 K1 C9 119.5(2) 2_655 3_665 ? C1 K1 C9 91.9(2) . 3_665 ? O8 K1 C9 49.66(19) 4_676 3_665 ? O11 K1 C9 70.8(2) . 3_665 ? C8 K1 C9 99.1(2) 2_655 3_665 ? O5 K1 H12A 82.9 3_565 . ? O1 K1 H12A 75.3 . . ? O6 K1 H12A 148.7 3_665 . ? O12 K1 H12A 16.1 . . ? O4 K1 H12A 89.7 2_655 . ? O2 K1 H12A 116.5 . . ? O3 K1 H12A 67.2 2_655 . ? C1 K1 H12A 96.2 . . ? O8 K1 H12A 90.9 4_676 . ? O11 K1 H12A 142.3 . . ? C8 K1 H12A 77.0 2_655 . ? C9 K1 H12A 138.4 3_665 . ? C1 O1 Sm1 125.9(6) . . ? C1 O1 K1 100.2(5) . . ? Sm1 O1 K1 133.7(3) . . ? C1 O2 K1 89.7(5) . . ? C8 O3 Sm1 152.8(6) . 3_665 ? C8 O3 K1 87.9(5) . 2_645 ? Sm1 O3 K1 107.0(2) 3_665 2_645 ? C8 O4 Sm1 151.8(6) . 3_565 ? C8 O4 K1 105.2(6) . 2_645 ? Sm1 O4 K1 102.2(2) 3_565 2_645 ? C9 O5 Sm1 92.9(6) . 2_544 ? C9 O5 K1 140.2(6) . 3_565 ? Sm1 O5 K1 120.9(3) 2_544 3_565 ? C9 O6 Sm1 91.7(5) . 2_544 ? C9 O6 K1 117.2(6) . 3_665 ? Sm1 O6 K1 101.7(2) 2_544 3_665 ? C7 O8 Sm1 124.6(6) . . ? C7 O8 K1 111.1(6) . 4_475 ? Sm1 O8 K1 92.0(2) . 4_475 ? C6 N1 C2 120.6(8) . . ? C6 N1 Sm1 119.3(6) . . ? C2 N1 Sm1 119.9(6) . . ? O2 C1 O1 124.5(8) . . ? O2 C1 C2 118.2(8) . . ? O1 C1 C2 117.3(7) . . ? O2 C1 K1 67.6(5) . . ? O1 C1 K1 57.0(4) . . ? C2 C1 K1 173.8(6) . . ? N1 C2 C3 121.5(8) . . ? N1 C2 C1 112.5(7) . . ? C3 C2 C1 126.0(8) . . ? C2 C3 C4 118.2(8) . . ? C2 C3 C8 123.8(8) . . ? C4 C3 C8 117.9(8) . . ? C5 C4 C3 120.5(8) . . ? C5 C4 H4 119.8 . . ? C3 C4 H4 119.8 . . ? C4 C5 C6 117.8(8) . . ? C4 C5 C9 119.4(8) . . ? C6 C5 C9 122.9(8) . . ? N1 C6 C5 121.4(8) . . ? N1 C6 C7 114.4(8) . . ? C5 C6 C7 124.1(8) . . ? O7 C7 O8 126.0(9) . . ? O7 C7 C6 117.7(8) . . ? O8 C7 C6 116.2(8) . . ? O4 C8 O3 124.2(9) . . ? O4 C8 C3 116.7(8) . . ? O3 C8 C3 119.1(8) . . ? O4 C8 K1 54.0(5) . 2_645 ? O3 C8 K1 70.5(5) . 2_645 ? C3 C8 K1 169.5(6) . 2_645 ? O5 C9 O6 121.0(9) . . ? O5 C9 C5 120.8(8) . . ? O6 C9 C5 117.8(9) . . ? O5 C9 Sm1 61.9(5) . 2_544 ? O6 C9 Sm1 62.2(5) . 2_544 ? C5 C9 Sm1 156.4(6) . 2_544 ? O5 C9 K1 134.8(6) . 3_665 ? O6 C9 K1 44.0(5) . 3_665 ? C5 C9 K1 86.2(5) . 3_665 ? Sm1 C9 K1 79.2(2) 2_544 3_665 ? Sm1 O9 H9B 109.7 . . ? Sm1 O9 H9C 109.7 . . ? H9B O9 H9C 108.2 . . ? Sm1 O10 H10A 123.2 . . ? Sm1 O10 H10B 116.4 . . ? H10A O10 H10B 107.7 . . ? K1 O11 H11A 77.1 . . ? K1 O11 H11B 160.2 . . ? H11A O11 H11B 107.7 . . ? K1 O12 H12A 98.9 . . ? K1 O12 H12B 124.7 . . ? H12A O12 H12B 107.7 . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag O3 Sm1 O1 C1 -70.3(7) 3_665 . . . ? O4 Sm1 O1 C1 73.6(7) 3_565 . . . ? O8 Sm1 O1 C1 6.5(8) . . . . ? O9 Sm1 O1 C1 142.8(7) . . . . ? O10 Sm1 O1 C1 -145.1(7) . . . . ? N1 Sm1 O1 C1 3.3(6) . . . . ? O5 Sm1 O1 C1 -105.2(7) 2_554 . . . ? O6 Sm1 O1 C1 140.3(6) 2_554 . . . ? C9 Sm1 O1 C1 -146.7(9) 2_554 . . . ? K1 Sm1 O1 C1 76.4(7) 4_475 . . . ? K1 Sm1 O1 C1 -81.5(7) 4_575 . . . ? O3 Sm1 O1 K1 103.3(4) 3_665 . . . ? O4 Sm1 O1 K1 -112.8(4) 3_565 . . . ? O8 Sm1 O1 K1 -179.9(3) . . . . ? O9 Sm1 O1 K1 -43.7(3) . . . . ? O10 Sm1 O1 K1 28.5(4) . . . . ? N1 Sm1 O1 K1 176.8(4) . . . . ? O5 Sm1 O1 K1 68.4(5) 2_554 . . . ? O6 Sm1 O1 K1 -46.1(7) 2_554 . . . ? C9 Sm1 O1 K1 26.9(12) 2_554 . . . ? K1 Sm1 O1 K1 -110.1(3) 4_475 . . . ? K1 Sm1 O1 K1 92.1(3) 4_575 . . . ? O5 K1 O1 C1 -75.7(5) 3_565 . . . ? O6 K1 O1 C1 54.8(5) 3_665 . . . ? O12 K1 O1 C1 -167.5(5) . . . . ? O4 K1 O1 C1 155.0(6) 2_655 . . . ? O2 K1 O1 C1 -1.6(5) . . . . ? O3 K1 O1 C1 -127.8(5) 2_655 . . . ? O8 K1 O1 C1 117.6(5) 4_676 . . . ? O11 K1 O1 C1 -8.1(6) . . . . ? C8 K1 O1 C1 -156.0(5) 2_655 . . . ? C9 K1 O1 C1 66.5(5) 3_665 . . . ? O5 K1 O1 Sm1 109.6(4) 3_565 . . . ? O6 K1 O1 Sm1 -119.9(3) 3_665 . . . ? O12 K1 O1 Sm1 17.8(4) . . . . ? O4 K1 O1 Sm1 -19.7(8) 2_655 . . . ? O2 K1 O1 Sm1 -176.3(5) . . . . ? O3 K1 O1 Sm1 57.5(5) 2_655 . . . ? C1 K1 O1 Sm1 -174.7(7) . . . . ? O8 K1 O1 Sm1 -57.1(4) 4_676 . . . ? O11 K1 O1 Sm1 177.2(3) . . . . ? C8 K1 O1 Sm1 29.3(7) 2_655 . . . ? C9 K1 O1 Sm1 -108.2(4) 3_665 . . . ? O5 K1 O2 C1 108.4(6) 3_565 . . . ? O1 K1 O2 C1 1.6(5) . . . . ? O6 K1 O2 C1 -130.4(6) 3_665 . . . ? O12 K1 O2 C1 20.3(7) . . . . ? O4 K1 O2 C1 -158.6(5) 2_655 . . . ? O3 K1 O2 C1 116.0(5) 2_655 . . . ? O8 K1 O2 C1 -80.8(6) 4_676 . . . ? O11 K1 O2 C1 176.6(6) . . . . ? C8 K1 O2 C1 150.8(6) 2_655 . . . ? C9 K1 O2 C1 -112.2(6) 3_665 . . . ? O1 Sm1 O8 C7 1.7(9) . . . . ? O3 Sm1 O8 C7 75.5(8) 3_665 . . . ? O4 Sm1 O8 C7 -74.3(8) 3_565 . . . ? O9 Sm1 O8 C7 -108.8(8) . . . . ? O10 Sm1 O8 C7 138.0(7) . . . . ? N1 Sm1 O8 C7 5.0(7) . . . . ? O5 Sm1 O8 C7 148.1(8) 2_554 . . . ? O6 Sm1 O8 C7 -158.2(8) 2_554 . . . ? C9 Sm1 O8 C7 175.0(9) 2_554 . . . ? K1 Sm1 O8 C7 -117.5(8) 4_475 . . . ? K1 Sm1 O8 C7 115.9(8) 4_575 . . . ? O1 Sm1 O8 K1 119.2(2) . . . 4_475 ? O3 Sm1 O8 K1 -167.0(2) 3_665 . . 4_475 ? O4 Sm1 O8 K1 43.17(19) 3_565 . . 4_475 ? O9 Sm1 O8 K1 8.7(4) . . . 4_475 ? O10 Sm1 O8 K1 -104.5(3) . . . 4_475 ? N1 Sm1 O8 K1 122.5(3) . . . 4_475 ? O5 Sm1 O8 K1 -94.4(2) 2_554 . . 4_475 ? O6 Sm1 O8 K1 -40.68(18) 2_554 . . 4_475 ? C9 Sm1 O8 K1 -67.5(2) 2_554 . . 4_475 ? K1 Sm1 O8 K1 -126.58(17) 4_575 . . 4_475 ? O1 Sm1 N1 C6 -179.5(7) . . . . ? O3 Sm1 N1 C6 -91.9(7) 3_665 . . . ? O4 Sm1 N1 C6 80.9(7) 3_565 . . . ? O8 Sm1 N1 C6 3.3(6) . . . . ? O9 Sm1 N1 C6 130.6(6) . . . . ? O10 Sm1 N1 C6 -128.5(6) . . . . ? O5 Sm1 N1 C6 -37.8(7) 2_554 . . . ? O6 Sm1 N1 C6 25.6(8) 2_554 . . . ? C9 Sm1 N1 C6 -8.0(8) 2_554 . . . ? K1 Sm1 N1 C6 45.0(6) 4_475 . . . ? K1 Sm1 N1 C6 -59.3(7) 4_575 . . . ? O1 Sm1 N1 C2 -4.6(6) . . . . ? O3 Sm1 N1 C2 83.1(7) 3_665 . . . ? O4 Sm1 N1 C2 -104.2(7) 3_565 . . . ? O8 Sm1 N1 C2 178.3(7) . . . . ? O9 Sm1 N1 C2 -54.4(7) . . . . ? O10 Sm1 N1 C2 46.5(8) . . . . ? O5 Sm1 N1 C2 137.2(6) 2_554 . . . ? O6 Sm1 N1 C2 -159.4(6) 2_554 . . . ? C9 Sm1 N1 C2 167.0(6) 2_554 . . . ? K1 Sm1 N1 C2 -140.0(6) 4_475 . . . ? K1 Sm1 N1 C2 115.7(6) 4_575 . . . ? K1 O2 C1 O1 -3.0(9) . . . . ? K1 O2 C1 C2 177.4(7) . . . . ? Sm1 O1 C1 O2 178.5(7) . . . . ? K1 O1 C1 O2 3.3(10) . . . . ? Sm1 O1 C1 C2 -1.8(10) . . . . ? K1 O1 C1 C2 -177.1(6) . . . . ? Sm1 O1 C1 K1 175.3(7) . . . . ? O5 K1 C1 O2 -70.9(6) 3_565 . . . ? O1 K1 C1 O2 -177.1(9) . . . . ? O6 K1 C1 O2 51.3(6) 3_665 . . . ? O12 K1 C1 O2 -163.8(6) . . . . ? O4 K1 C1 O2 78.1(15) 2_655 . . . ? O3 K1 C1 O2 -97.3(6) 2_655 . . . ? O8 K1 C1 O2 111.9(5) 4_676 . . . ? O11 K1 C1 O2 -3.6(6) . . . . ? C8 K1 C1 O2 -101.7(12) 2_655 . . . ? C9 K1 C1 O2 66.9(6) 3_665 . . . ? O5 K1 C1 O1 106.2(5) 3_565 . . . ? O6 K1 C1 O1 -131.6(5) 3_665 . . . ? O12 K1 C1 O1 13.3(6) . . . . ? O4 K1 C1 O1 -104.8(14) 2_655 . . . ? O2 K1 C1 O1 177.1(9) . . . . ? O3 K1 C1 O1 79.8(6) 2_655 . . . ? O8 K1 C1 O1 -71.0(5) 4_676 . . . ? O11 K1 C1 O1 173.5(5) . . . . ? C8 K1 C1 O1 75.4(13) 2_655 . . . ? C9 K1 C1 O1 -116.0(5) 3_665 . . . ? O5 K1 C1 C2 131(5) 3_565 . . . ? O1 K1 C1 C2 25(5) . . . . ? O6 K1 C1 C2 -107(5) 3_665 . . . ? O12 K1 C1 C2 38(5) . . . . ? O4 K1 C1 C2 -80(5) 2_655 . . . ? O2 K1 C1 C2 -158(5) . . . . ? O3 K1 C1 C2 105(5) 2_655 . . . ? O8 K1 C1 C2 -46(5) 4_676 . . . ? O11 K1 C1 C2 -162(5) . . . . ? C8 K1 C1 C2 100(5) 2_655 . . . ? C9 K1 C1 C2 -91(5) 3_665 . . . ? C6 N1 C2 C3 -2.1(13) . . . . ? Sm1 N1 C2 C3 -177.0(6) . . . . ? C6 N1 C2 C1 -179.8(7) . . . . ? Sm1 N1 C2 C1 5.3(9) . . . . ? O2 C1 C2 N1 177.2(8) . . . . ? O1 C1 C2 N1 -2.5(11) . . . . ? K1 C1 C2 N1 -26(6) . . . . ? O2 C1 C2 C3 -0.4(13) . . . . ? O1 C1 C2 C3 179.9(8) . . . . ? K1 C1 C2 C3 157(5) . . . . ? N1 C2 C3 C4 2.7(13) . . . . ? C1 C2 C3 C4 -179.9(8) . . . . ? N1 C2 C3 C8 -177.1(8) . . . . ? C1 C2 C3 C8 0.3(14) . . . . ? C2 C3 C4 C5 -0.7(14) . . . . ? C8 C3 C4 C5 179.1(8) . . . . ? C3 C4 C5 C6 -1.8(14) . . . . ? C3 C4 C5 C9 178.8(9) . . . . ? C2 N1 C6 C5 -0.6(13) . . . . ? Sm1 N1 C6 C5 174.3(7) . . . . ? C2 N1 C6 C7 175.6(8) . . . . ? Sm1 N1 C6 C7 -9.5(10) . . . . ? C4 C5 C6 N1 2.5(14) . . . . ? C9 C5 C6 N1 -178.1(8) . . . . ? C4 C5 C6 C7 -173.3(9) . . . . ? C9 C5 C6 C7 6.1(14) . . . . ? Sm1 O8 C7 O7 167.5(8) . . . . ? K1 O8 C7 O7 59.3(12) 4_475 . . . ? Sm1 O8 C7 C6 -11.5(12) . . . . ? K1 O8 C7 C6 -119.7(7) 4_475 . . . ? N1 C6 C7 O7 -165.7(9) . . . . ? C5 C6 C7 O7 10.4(14) . . . . ? N1 C6 C7 O8 13.4(12) . . . . ? C5 C6 C7 O8 -170.5(9) . . . . ? Sm1 O4 C8 O3 -158.5(9) 3_565 . . . ? K1 O4 C8 O3 7.5(10) 2_645 . . . ? Sm1 O4 C8 C3 19.8(17) 3_565 . . . ? K1 O4 C8 C3 -174.3(6) 2_645 . . . ? Sm1 O4 C8 K1 -166.0(14) 3_565 . . 2_645 ? Sm1 O3 C8 O4 118.2(12) 3_665 . . . ? K1 O3 C8 O4 -6.4(9) 2_645 . . . ? Sm1 O3 C8 C3 -60.0(16) 3_665 . . . ? K1 O3 C8 C3 175.4(7) 2_645 . . . ? Sm1 O3 C8 K1 124.6(13) 3_665 . . 2_645 ? C2 C3 C8 O4 98.2(11) . . . . ? C4 C3 C8 O4 -81.6(11) . . . . ? C2 C3 C8 O3 -83.5(11) . . . . ? C4 C3 C8 O3 96.7(11) . . . . ? C2 C3 C8 K1 72(3) . . . 2_645 ? C4 C3 C8 K1 -108(3) . . . 2_645 ? Sm1 O5 C9 O6 20.1(9) 2_544 . . . ? K1 O5 C9 O6 170.0(6) 3_565 . . . ? Sm1 O5 C9 C5 -153.0(7) 2_544 . . . ? K1 O5 C9 C5 -3.1(14) 3_565 . . . ? K1 O5 C9 Sm1 149.9(9) 3_565 . . 2_544 ? Sm1 O5 C9 K1 -34.1(8) 2_544 . . 3_665 ? K1 O5 C9 K1 115.8(8) 3_565 . . 3_665 ? Sm1 O6 C9 O5 -20.1(9) 2_544 . . . ? K1 O6 C9 O5 -124.1(8) 3_665 . . . ? Sm1 O6 C9 C5 153.2(7) 2_544 . . . ? K1 O6 C9 C5 49.2(9) 3_665 . . . ? K1 O6 C9 Sm1 -104.0(4) 3_665 . . 2_544 ? Sm1 O6 C9 K1 104.0(4) 2_544 . . 3_665 ? C4 C5 C9 O5 76.8(12) . . . . ? C6 C5 C9 O5 -102.6(11) . . . . ? C4 C5 C9 O6 -96.5(11) . . . . ? C6 C5 C9 O6 84.1(11) . . . . ? C4 C5 C9 Sm1 -13(2) . . . 2_544 ? C6 C5 C9 Sm1 167.8(11) . . . 2_544 ? C4 C5 C9 K1 -64.7(8) . . . 3_665 ? C6 C5 C9 K1 115.9(9) . . . 3_665 ? _diffrn_measured_fraction_theta_max 0.998 _diffrn_reflns_theta_full 26.00 _diffrn_measured_fraction_theta_full 0.998 _refine_diff_density_max 3.166 _refine_diff_density_min -1.881 _refine_diff_density_rms 0.249 # Attachment '- complex 3.cif' data_r91002f _database_code_depnum_ccdc_archive 'CCDC 768998' #TrackingRef '- complex 3.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C9 H10 N O12 Pr' _chemical_formula_weight 465.09 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 Triclinic _symmetry_space_group_name_H-M P-1 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 8.4864(17) _cell_length_b 8.9615(18) _cell_length_c 9.4369(19) _cell_angle_alpha 95.53(3) _cell_angle_beta 115.45(3) _cell_angle_gamma 95.45(3) _cell_volume 637.6(2) _cell_formula_units_Z 2 _cell_measurement_temperature 113(2) _cell_measurement_reflns_used 2208 _cell_measurement_theta_min 2.360 _cell_measurement_theta_max 27.872 _exptl_crystal_description ? _exptl_crystal_colour ? _exptl_crystal_size_max 0.18 _exptl_crystal_size_mid 0.16 _exptl_crystal_size_min 0.10 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 2.423 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 452 _exptl_absorpt_coefficient_mu 3.896 _exptl_absorpt_correction_type MULTI-SCAN _exptl_absorpt_correction_T_min 0.5406 _exptl_absorpt_correction_T_max 0.6967 _exptl_absorpt_process_details crystalclear _exptl_special_details ; ? ; _diffrn_ambient_temperature 113(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 'rigaku saturn CCD area detector' _diffrn_measurement_method '\w and \f scans' _diffrn_detector_area_resol_mean 7.31 _diffrn_standards_number 0 _diffrn_standards_interval_count 0 _diffrn_standards_interval_time 0 _diffrn_standards_decay_% 0 _diffrn_reflns_number 5531 _diffrn_reflns_av_R_equivalents 0.0354 _diffrn_reflns_av_sigmaI/netI 0.0696 _diffrn_reflns_limit_h_min -10 _diffrn_reflns_limit_h_max 10 _diffrn_reflns_limit_k_min -11 _diffrn_reflns_limit_k_max 11 _diffrn_reflns_limit_l_min -12 _diffrn_reflns_limit_l_max 11 _diffrn_reflns_theta_min 2.31 _diffrn_reflns_theta_max 27.81 _reflns_number_total 2910 _reflns_number_gt 2557 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'crystalclear(Rigaku/MSC Inc., 2005)' _computing_cell_refinement crystalclear _computing_data_reduction crystalclear _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^)+(0.0150P)^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 2910 _refine_ls_number_parameters 209 _refine_ls_number_restraints 6 _refine_ls_R_factor_all 0.0309 _refine_ls_R_factor_gt 0.0275 _refine_ls_wR_factor_ref 0.0609 _refine_ls_wR_factor_gt 0.0602 _refine_ls_goodness_of_fit_ref 1.023 _refine_ls_restrained_S_all 1.022 _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 Pr1 Pr 0.67971(2) 0.30371(2) 0.30549(2) 0.00600(7) Uani 1 1 d . . . O1 O 0.4128(3) 0.0971(3) 0.1586(3) 0.0088(6) Uani 1 1 d . . . O2 O 0.1631(3) -0.0686(3) 0.0312(3) 0.0111(6) Uani 1 1 d . . . H2A H 0.1759 -0.0513 -0.0495 0.017 Uiso 1 1 calc R . . O3 O 0.3715(4) -0.2517(3) 0.2372(3) 0.0206(7) Uani 1 1 d . . . O4 O 0.3611(3) -0.3333(3) 0.4508(3) 0.0108(6) Uani 1 1 d . . . O5 O 0.2212(3) -0.0764(3) 0.7880(3) 0.0092(6) Uani 1 1 d . . . O6 O 0.1854(4) 0.1681(3) 0.7943(3) 0.0168(7) Uani 1 1 d . . . O7 O -0.0199(3) 0.3246(3) 0.5165(3) 0.0095(6) Uani 1 1 d . . . O8 O 0.2643(3) 0.4243(3) 0.6084(3) 0.0122(6) Uani 1 1 d . . . O9 O 0.4041(3) 0.4150(3) 0.2403(3) 0.0158(6) Uani 1 1 d . . . H9A H 0.3959 0.4839 0.3046 0.024 Uiso 1 1 d R . . H9B H 0.3153 0.3965 0.1501 0.024 Uiso 1 1 d R . . O10 O 0.9217(3) 0.4252(3) 0.2283(3) 0.0142(6) Uani 1 1 d . . . H10A H 0.9001 0.4691 0.1476 0.021 Uiso 1 1 d R . . H10B H 0.9765 0.4895 0.3124 0.021 Uiso 1 1 d R . . O11 O 0.5518(4) 0.3297(4) 0.0130(3) 0.0258(8) Uani 1 1 d . . . H11A H 0.6020 0.3337 -0.0481 0.039 Uiso 1 1 d R . . H11B H 0.4542 0.2701 -0.0282 0.039 Uiso 1 1 d R . . N1 N 0.2750(4) -0.0748(4) 0.5343(3) 0.0064(6) Uani 1 1 d . . . C1 C 0.3461(5) -0.2366(4) 0.3574(4) 0.0090(8) Uani 1 1 d . . . C2 C 0.2900(5) -0.0899(4) 0.3977(4) 0.0053(7) Uani 1 1 d . . . C3 C 0.2569(5) 0.0259(4) 0.3042(4) 0.0069(8) Uani 1 1 d . . . C4 C 0.2055(4) 0.1553(4) 0.3519(4) 0.0078(8) Uani 1 1 d . . . H4 H 0.1828 0.2347 0.2892 0.009 Uiso 1 1 calc R . . C5 C 0.1866(4) 0.1698(4) 0.4926(4) 0.0059(8) Uani 1 1 d . . . C6 C 0.2232(5) 0.0495(4) 0.5798(4) 0.0057(7) Uani 1 1 d . . . C7 C 0.2085(5) 0.0501(4) 0.7338(4) 0.0080(8) Uani 1 1 d . . . C8 C 0.2863(5) 0.0183(4) 0.1569(4) 0.0073(8) Uani 1 1 d U . . C9 C 0.1386(5) 0.3163(4) 0.5448(4) 0.0065(8) Uani 1 1 d . . . O12 O 0.9149(3) 0.6516(3) 0.0281(3) 0.0158(6) Uani 1 1 d . . . H12A H 0.8773 0.7106 0.0789 0.024 Uiso 1 1 d R . . H12B H 1.0191 0.6873 0.0455 0.024 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 0.00804(14) 0.00338(12) 0.00740(12) 0.00163(8) 0.00386(10) 0.00173(9) O1 0.0083(14) 0.0080(14) 0.0110(13) 0.0000(10) 0.0059(12) -0.0015(11) O2 0.0111(15) 0.0173(17) 0.0039(13) -0.0003(11) 0.0034(12) -0.0008(11) O3 0.0345(18) 0.0220(19) 0.0175(15) 0.0087(13) 0.0193(14) 0.0163(14) O4 0.0123(14) 0.0103(16) 0.0140(14) 0.0059(11) 0.0080(12) 0.0067(11) O5 0.0170(15) 0.0061(14) 0.0081(13) 0.0043(10) 0.0077(12) 0.0040(11) O6 0.0351(18) 0.0093(16) 0.0142(14) 0.0054(11) 0.0161(14) 0.0112(13) O7 0.0100(15) 0.0076(15) 0.0114(13) 0.0024(11) 0.0049(12) 0.0020(11) O8 0.0112(15) 0.0026(15) 0.0249(16) -0.0002(11) 0.0104(13) 0.0017(11) O9 0.0118(15) 0.0102(16) 0.0194(15) -0.0036(12) 0.0020(13) 0.0038(12) O10 0.0180(16) 0.0112(16) 0.0130(14) 0.0007(11) 0.0074(12) -0.0018(12) O11 0.0168(17) 0.050(2) 0.0121(15) 0.0067(15) 0.0080(13) 0.0015(15) N1 0.0042(16) 0.0059(17) 0.0070(15) -0.0003(12) 0.0014(13) -0.0014(12) C1 0.008(2) 0.007(2) 0.0111(19) -0.0007(14) 0.0040(16) 0.0035(15) C2 0.0047(19) 0.0039(19) 0.0087(18) -0.0005(14) 0.0048(15) -0.0004(14) C3 0.0042(19) 0.011(2) 0.0059(17) 0.0028(14) 0.0023(15) 0.0003(15) C4 0.006(2) 0.008(2) 0.0087(18) 0.0026(14) 0.0027(16) -0.0021(15) C5 0.0032(19) 0.005(2) 0.0088(18) -0.0014(14) 0.0032(15) -0.0028(14) C6 0.0044(19) 0.0051(19) 0.0069(17) 0.0011(14) 0.0021(15) -0.0002(14) C7 0.007(2) 0.009(2) 0.0058(18) -0.0006(14) 0.0018(16) -0.0008(15) C8 0.011(2) 0.0042(19) 0.0083(18) 0.0021(14) 0.0047(16) 0.0060(15) C9 0.012(2) 0.005(2) 0.0055(17) 0.0040(14) 0.0051(16) 0.0045(15) O12 0.0153(16) 0.0175(17) 0.0180(15) -0.0015(12) 0.0108(13) 0.0055(12) _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 O8 2.428(3) 2_666 ? Pr1 O7 2.444(3) 1_655 ? Pr1 O4 2.463(3) 2_656 ? Pr1 O9 2.484(3) . ? Pr1 O5 2.500(3) 2_656 ? Pr1 O11 2.539(3) . ? Pr1 O1 2.548(3) . ? Pr1 N1 2.625(3) 2_656 ? Pr1 O10 2.636(3) . ? O1 C8 1.220(4) . ? O2 C8 1.307(4) . ? O2 H2A 0.8400 . ? O3 C1 1.239(4) . ? O4 C1 1.271(4) . ? O4 Pr1 2.463(3) 2_656 ? O5 C7 1.283(4) . ? O5 Pr1 2.500(3) 2_656 ? O6 C7 1.226(5) . ? O7 C9 1.265(4) . ? O7 Pr1 2.444(3) 1_455 ? O8 C9 1.256(4) . ? O8 Pr1 2.428(3) 2_666 ? O9 H9A 0.8519 . ? O9 H9B 0.8475 . ? O10 H10A 0.8487 . ? O10 H10B 0.8493 . ? O11 H11A 0.8528 . ? O11 H11B 0.8491 . ? N1 C6 1.336(5) . ? N1 C2 1.344(4) . ? N1 Pr1 2.625(3) 2_656 ? C1 C2 1.509(5) . ? C2 C3 1.397(5) . ? C3 C4 1.379(5) . ? C3 C8 1.511(5) . ? C4 C5 1.400(5) . ? C4 H4 0.9500 . ? C5 C6 1.396(5) . ? C5 C9 1.510(5) . ? C6 C7 1.511(5) . ? O12 H12A 0.8529 . ? O12 H12B 0.8503 . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag O8 Pr1 O7 81.19(10) 2_666 1_655 ? O8 Pr1 O4 75.38(9) 2_666 2_656 ? O7 Pr1 O4 76.80(9) 1_655 2_656 ? O8 Pr1 O9 67.32(9) 2_666 . ? O7 Pr1 O9 140.81(9) 1_655 . ? O4 Pr1 O9 73.21(9) 2_656 . ? O8 Pr1 O5 147.73(8) 2_666 2_656 ? O7 Pr1 O5 79.27(9) 1_655 2_656 ? O4 Pr1 O5 123.91(8) 2_656 2_656 ? O9 Pr1 O5 139.03(9) . 2_656 ? O8 Pr1 O11 93.53(10) 2_666 . ? O7 Pr1 O11 133.85(9) 1_655 . ? O4 Pr1 O11 146.18(9) 2_656 . ? O9 Pr1 O11 73.03(10) . . ? O5 Pr1 O11 82.01(10) 2_656 . ? O8 Pr1 O1 137.54(8) 2_666 . ? O7 Pr1 O1 137.02(9) 1_655 . ? O4 Pr1 O1 93.83(8) 2_656 . ? O9 Pr1 O1 70.24(9) . . ? O5 Pr1 O1 71.59(9) 2_656 . ? O11 Pr1 O1 72.75(9) . . ? O8 Pr1 N1 131.49(9) 2_666 2_656 ? O7 Pr1 N1 67.28(9) 1_655 2_656 ? O4 Pr1 N1 62.49(9) 2_656 2_656 ? O9 Pr1 N1 117.51(9) . 2_656 ? O5 Pr1 N1 61.53(9) 2_656 2_656 ? O11 Pr1 N1 134.92(10) . 2_656 ? O1 Pr1 N1 71.20(9) . 2_656 ? O8 Pr1 O10 71.50(9) 2_666 . ? O7 Pr1 O10 66.85(8) 1_655 . ? O4 Pr1 O10 133.58(9) 2_656 . ? O9 Pr1 O10 120.04(9) . . ? O5 Pr1 O10 77.28(8) 2_656 . ? O11 Pr1 O10 68.03(9) . . ? O1 Pr1 O10 132.47(8) . . ? N1 Pr1 O10 122.36(9) 2_656 . ? C8 O1 Pr1 149.1(2) . . ? C8 O2 H2A 109.5 . . ? C1 O4 Pr1 127.3(2) . 2_656 ? C7 O5 Pr1 126.8(2) . 2_656 ? C9 O7 Pr1 144.1(2) . 1_455 ? C9 O8 Pr1 140.5(2) . 2_666 ? Pr1 O9 H9A 121.9 . . ? Pr1 O9 H9B 123.9 . . ? H9A O9 H9B 113.8 . . ? Pr1 O10 H10A 124.7 . . ? Pr1 O10 H10B 96.3 . . ? H10A O10 H10B 109.7 . . ? Pr1 O11 H11A 129.9 . . ? Pr1 O11 H11B 103.8 . . ? H11A O11 H11B 113.3 . . ? C6 N1 C2 120.2(3) . . ? C6 N1 Pr1 120.8(2) . 2_656 ? C2 N1 Pr1 118.8(2) . 2_656 ? O3 C1 O4 126.6(4) . . ? O3 C1 C2 117.5(3) . . ? O4 C1 C2 116.0(3) . . ? N1 C2 C3 120.6(3) . . ? N1 C2 C1 115.3(3) . . ? C3 C2 C1 124.2(3) . . ? C4 C3 C2 119.4(3) . . ? C4 C3 C8 118.5(3) . . ? C2 C3 C8 122.0(3) . . ? C3 C4 C5 120.1(3) . . ? C3 C4 H4 120.0 . . ? C5 C4 H4 120.0 . . ? C6 C5 C4 117.1(4) . . ? C6 C5 C9 124.4(3) . . ? C4 C5 C9 118.4(3) . . ? N1 C6 C5 122.7(3) . . ? N1 C6 C7 114.6(3) . . ? C5 C6 C7 122.7(3) . . ? O6 C7 O5 126.4(3) . . ? O6 C7 C6 118.3(3) . . ? O5 C7 C6 115.3(3) . . ? O1 C8 O2 124.6(3) . . ? O1 C8 C3 119.9(3) . . ? O2 C8 C3 115.3(3) . . ? O8 C9 O7 125.3(4) . . ? O8 C9 C5 114.7(3) . . ? O7 C9 C5 119.9(3) . . ? H12A O12 H12B 110.3 . . ? 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 O8 Pr1 O1 C8 -70.2(5) 2_666 . . . ? O7 Pr1 O1 C8 77.0(5) 1_655 . . . ? O4 Pr1 O1 C8 2.3(5) 2_656 . . . ? O9 Pr1 O1 C8 -68.3(5) . . . . ? O5 Pr1 O1 C8 126.8(5) 2_656 . . . ? O11 Pr1 O1 C8 -146.0(5) . . . . ? N1 Pr1 O1 C8 61.5(5) 2_656 . . . ? O10 Pr1 O1 C8 178.6(4) . . . . ? Pr1 O4 C1 O3 178.0(3) 2_656 . . . ? Pr1 O4 C1 C2 -2.6(4) 2_656 . . . ? C6 N1 C2 C3 2.0(5) . . . . ? Pr1 N1 C2 C3 176.3(2) 2_656 . . . ? C6 N1 C2 C1 -178.8(3) . . . . ? Pr1 N1 C2 C1 -4.5(4) 2_656 . . . ? O3 C1 C2 N1 -176.0(3) . . . . ? O4 C1 C2 N1 4.6(5) . . . . ? O3 C1 C2 C3 3.2(5) . . . . ? O4 C1 C2 C3 -176.2(3) . . . . ? N1 C2 C3 C4 -1.1(5) . . . . ? C1 C2 C3 C4 179.7(3) . . . . ? N1 C2 C3 C8 175.1(3) . . . . ? C1 C2 C3 C8 -4.1(5) . . . . ? C2 C3 C4 C5 -0.1(5) . . . . ? C8 C3 C4 C5 -176.4(3) . . . . ? C3 C4 C5 C6 0.5(5) . . . . ? C3 C4 C5 C9 177.1(3) . . . . ? C2 N1 C6 C5 -1.6(5) . . . . ? Pr1 N1 C6 C5 -175.8(3) 2_656 . . . ? C2 N1 C6 C7 178.8(3) . . . . ? Pr1 N1 C6 C7 4.6(4) 2_656 . . . ? C4 C5 C6 N1 0.3(5) . . . . ? C9 C5 C6 N1 -176.1(3) . . . . ? C4 C5 C6 C7 179.9(3) . . . . ? C9 C5 C6 C7 3.5(5) . . . . ? Pr1 O5 C7 O6 -168.4(3) 2_656 . . . ? Pr1 O5 C7 C6 11.9(4) 2_656 . . . ? N1 C6 C7 O6 170.2(3) . . . . ? C5 C6 C7 O6 -9.5(5) . . . . ? N1 C6 C7 O5 -10.1(5) . . . . ? C5 C6 C7 O5 170.3(3) . . . . ? Pr1 O1 C8 O2 170.4(3) . . . . ? Pr1 O1 C8 C3 -4.9(7) . . . . ? C4 C3 C8 O1 70.2(5) . . . . ? C2 C3 C8 O1 -106.0(4) . . . . ? C4 C3 C8 O2 -105.5(4) . . . . ? C2 C3 C8 O2 78.2(4) . . . . ? Pr1 O8 C9 O7 -7.5(6) 2_666 . . . ? Pr1 O8 C9 C5 169.1(2) 2_666 . . . ? Pr1 O7 C9 O8 115.8(4) 1_455 . . . ? Pr1 O7 C9 C5 -60.7(5) 1_455 . . . ? C6 C5 C9 O8 98.5(4) . . . . ? C4 C5 C9 O8 -77.8(4) . . . . ? C6 C5 C9 O7 -84.6(4) . . . . ? C4 C5 C9 O7 99.0(4) . . . . ? _diffrn_measured_fraction_theta_max 0.964 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 0.969 _refine_diff_density_max 0.960 _refine_diff_density_min -1.280 _refine_diff_density_rms 0.175 # Attachment '- complex 1.cif' data_r91110g1 _database_code_depnum_ccdc_archive 'CCDC 768999' #TrackingRef '- complex 1.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C9 H10 La N O12' _chemical_formula_weight 463.09 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 8.4917(17) _cell_length_b 9.0243(18) _cell_length_c 9.0255(18) _cell_angle_alpha 78.37(3) _cell_angle_beta 65.06(3) _cell_angle_gamma 84.04(3) _cell_volume 614.1(2) _cell_formula_units_Z 2 _cell_measurement_temperature 113(2) _cell_measurement_reflns_used 2301 _cell_measurement_theta_min 2.2945 _cell_measurement_theta_max 27.801 _exptl_crystal_description ? _exptl_crystal_colour ? _exptl_crystal_size_max 0.10 _exptl_crystal_size_mid 0.08 _exptl_crystal_size_min 0.04 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 2.504 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 448 _exptl_absorpt_coefficient_mu 3.556 _exptl_absorpt_correction_type MULTI-SCAN _exptl_absorpt_correction_T_min 0.7175 _exptl_absorpt_correction_T_max 0.8708 _exptl_absorpt_process_details crystalclear _exptl_special_details ; ? ; _diffrn_ambient_temperature 113(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'rotating anode' _diffrn_radiation_monochromator multilayer _diffrn_measurement_device_type 'rigaku saturn CCD area detector' _diffrn_measurement_method '\w and \f scans' _diffrn_detector_area_resol_mean 7.31 _diffrn_standards_number 0 _diffrn_standards_interval_count 0 _diffrn_standards_interval_time 0 _diffrn_standards_decay_% 0 _diffrn_reflns_number 8109 _diffrn_reflns_av_R_equivalents 0.0296 _diffrn_reflns_av_sigmaI/netI 0.0351 _diffrn_reflns_limit_h_min -10 _diffrn_reflns_limit_h_max 11 _diffrn_reflns_limit_k_min -11 _diffrn_reflns_limit_k_max 11 _diffrn_reflns_limit_l_min -12 _diffrn_reflns_limit_l_max 12 _diffrn_reflns_theta_min 2.30 _diffrn_reflns_theta_max 29.95 _reflns_number_total 3027 _reflns_number_gt 2825 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'crystalclear(Rigaku/MSC Inc., 2005)' _computing_cell_refinement crystalclear _computing_data_reduction crystalclear _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^)+(0.0288P)^2^+0.1838P] 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 SHELXL _refine_ls_extinction_coef 0.0240(11) _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_number_reflns 3027 _refine_ls_number_parameters 230 _refine_ls_number_restraints 15 _refine_ls_R_factor_all 0.0268 _refine_ls_R_factor_gt 0.0239 _refine_ls_wR_factor_ref 0.0571 _refine_ls_wR_factor_gt 0.0558 _refine_ls_goodness_of_fit_ref 1.131 _refine_ls_restrained_S_all 1.130 _refine_ls_shift/su_max 0.002 _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 -0.37198(2) 0.304915(17) 0.694658(18) 0.00564(8) Uani 1 1 d . . . O1 O -0.2546(3) 0.0990(2) 0.8458(2) 0.0094(4) Uani 1 1 d . . . O2 O -0.1327(3) -0.0672(2) 0.9705(2) 0.0095(4) Uani 1 1 d U . . H2 H -0.222(5) -0.064(4) 1.044(5) 0.011 Uiso 1 1 d . . . O3 O -0.1433(3) -0.2420(3) 0.7638(3) 0.0194(5) Uani 1 1 d . . . O4 O 0.0810(3) -0.3309(2) 0.5559(3) 0.0104(4) Uani 1 1 d . . . O5 O 0.5664(3) -0.0738(2) 0.2113(2) 0.0075(4) Uani 1 1 d . . . O6 O 0.6092(3) 0.1680(3) 0.2084(3) 0.0180(5) Uani 1 1 d . . . O7 O 0.5354(3) 0.3235(2) 0.4832(2) 0.0085(4) Uani 1 1 d . . . O8 O 0.3423(3) 0.4212(2) 0.3958(3) 0.0126(5) Uani 1 1 d . . . O9 O -0.1537(3) 0.4185(3) 0.7548(3) 0.0137(5) Uani 1 1 d D . . H9A H -0.136(4) 0.391(4) 0.842(3) 0.016 Uiso 1 1 d D . . H9B H -0.096(4) 0.494(3) 0.687(3) 0.016 Uiso 1 1 d D . . O10 O -0.6959(3) 0.4287(2) 0.7714(3) 0.0133(4) Uani 1 1 d D . . H10A H -0.664(4) 0.495(3) 0.683(2) 0.016 Uiso 1 1 d D . . H10B H -0.763(4) 0.462(3) 0.859(2) 0.016 Uiso 1 1 d D . . O11 O -0.5383(3) 0.3433(3) 0.9898(3) 0.0205(5) Uani 1 1 d . . . H11B H -0.4699 0.3072 1.0356 0.025 Uiso 1 1 d R . . H11A H -0.6385 0.3174 1.0644 0.025 Uiso 1 1 d R . . N1 N 0.2563(3) -0.0738(3) 0.4673(3) 0.0055(5) Uani 1 1 d . . . C1 C -0.1295(4) 0.0190(3) 0.8461(3) 0.0069(5) Uani 1 1 d . . . C2 C 0.0462(4) 0.0257(3) 0.6989(3) 0.0064(5) Uani 1 1 d . . . C3 C 0.1477(4) 0.1539(3) 0.6501(3) 0.0074(5) Uani 1 1 d . . . H3 H 0.1089 0.2330 0.7135 0.009 Uiso 1 1 calc R . . C4 C 0.3055(4) 0.1676(3) 0.5092(3) 0.0067(5) Uani 1 1 d . . . C5 C 0.3552(4) 0.0494(3) 0.4213(3) 0.0067(5) Uani 1 1 d . . . C6 C 0.1053(4) -0.0876(3) 0.6035(3) 0.0063(5) Uani 1 1 d . . . C7 C 0.0046(4) -0.2316(3) 0.6456(3) 0.0089(6) Uani 1 1 d . . . C8 C 0.5234(4) 0.0507(3) 0.2676(3) 0.0078(5) Uani 1 1 d . . . C9 C 0.4057(4) 0.3142(3) 0.4565(3) 0.0058(5) Uani 1 1 d . . . O12 O 0.8879(3) 0.3466(3) 0.0263(3) 0.0153(5) Uani 1 1 d D . . H12A H 0.815(3) 0.277(3) 0.077(4) 0.018 Uiso 1 1 d D . . H12B H 0.9894(19) 0.330(4) 0.019(5) 0.018 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 0.00795(11) 0.00477(10) 0.00461(9) -0.00046(6) -0.00318(7) 0.00001(6) O1 0.0097(11) 0.0110(10) 0.0067(9) 0.0004(8) -0.0040(8) 0.0020(8) O2 0.0082(10) 0.0153(11) 0.0011(9) 0.0018(8) 0.0000(8) 0.0015(9) O3 0.0178(13) 0.0188(12) 0.0139(11) -0.0073(9) 0.0047(10) -0.0097(10) O4 0.0143(11) 0.0087(10) 0.0086(10) -0.0028(8) -0.0042(9) -0.0023(8) O5 0.0095(10) 0.0070(10) 0.0048(9) -0.0026(7) -0.0011(8) 0.0003(8) O6 0.0212(13) 0.0118(11) 0.0119(11) -0.0031(9) 0.0041(10) -0.0079(10) O7 0.0115(11) 0.0090(10) 0.0066(9) 0.0009(8) -0.0061(9) -0.0008(8) O8 0.0169(12) 0.0072(10) 0.0187(11) 0.0019(8) -0.0139(10) -0.0001(9) O9 0.0230(13) 0.0110(11) 0.0114(10) 0.0039(8) -0.0125(10) -0.0066(9) O10 0.0150(12) 0.0128(11) 0.0097(10) -0.0002(8) -0.0040(9) 0.0012(9) O11 0.0129(12) 0.0401(16) 0.0081(10) -0.0060(10) -0.0025(9) -0.0027(11) N1 0.0073(12) 0.0061(11) 0.0031(10) 0.0020(8) -0.0033(10) -0.0001(9) C1 0.0096(14) 0.0066(13) 0.0056(12) -0.0002(10) -0.0037(11) -0.0038(11) C2 0.0082(14) 0.0089(13) 0.0027(12) -0.0008(10) -0.0030(11) 0.0009(11) C3 0.0077(14) 0.0093(13) 0.0063(12) -0.0022(10) -0.0043(11) 0.0029(11) C4 0.0083(14) 0.0074(13) 0.0060(12) -0.0003(10) -0.0053(11) 0.0020(11) C5 0.0072(14) 0.0073(13) 0.0058(12) 0.0002(10) -0.0039(11) 0.0010(11) C6 0.0069(14) 0.0058(13) 0.0064(12) 0.0001(10) -0.0036(11) 0.0010(10) C7 0.0104(15) 0.0104(14) 0.0054(12) -0.0001(10) -0.0032(12) -0.0011(11) C8 0.0102(14) 0.0078(13) 0.0050(12) 0.0007(10) -0.0033(11) -0.0006(11) C9 0.0086(14) 0.0045(12) 0.0032(11) -0.0015(9) -0.0012(11) 0.0001(10) O12 0.0150(12) 0.0186(12) 0.0123(11) 0.0026(9) -0.0068(10) -0.0054(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 2.324(2) 1_455 ? La1 O8 2.446(2) 2_566 ? La1 O1 2.459(2) . ? La1 O9 2.500(2) . ? La1 O11 2.511(2) . ? La1 O4 2.544(2) 2_556 ? La1 O5 2.572(2) 2_556 ? La1 N1 2.654(3) 2_556 ? La1 O10 2.713(2) . ? O1 C1 1.222(4) . ? O2 C1 1.222(3) . ? O2 H2 0.77(4) . ? O3 C7 1.256(4) . ? O4 C7 1.268(4) . ? O4 La1 2.544(2) 2_556 ? O5 C8 1.282(4) . ? O5 La1 2.572(2) 2_556 ? O6 C8 1.241(4) . ? O7 C9 1.237(3) . ? O7 La1 2.324(2) 1_655 ? O8 C9 1.204(3) . ? O8 La1 2.446(2) 2_566 ? O9 H9A 0.847(10) . ? O9 H9B 0.851(10) . ? O10 H10A 0.852(10) . ? O10 H10B 0.850(10) . ? O11 H11B 0.8500 . ? O11 H11A 0.8527 . ? N1 C6 1.346(4) . ? N1 C5 1.352(4) . ? N1 La1 2.654(3) 2_556 ? C1 C2 1.519(4) . ? C2 C6 1.387(4) . ? C2 C3 1.399(4) . ? C3 C4 1.401(4) . ? C3 H3 0.9500 . ? C4 C5 1.383(4) . ? C4 C9 1.529(4) . ? C5 C8 1.513(4) . ? C6 C7 1.524(4) . ? O12 H12A 0.846(10) . ? O12 H12B 0.836(10) . ? 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 O8 83.26(7) 1_455 2_566 ? O7 La1 O1 134.76(7) 1_455 . ? O8 La1 O1 137.89(7) 2_566 . ? O7 La1 O9 139.57(7) 1_455 . ? O8 La1 O9 65.03(7) 2_566 . ? O1 La1 O9 72.93(7) . . ? O7 La1 O11 130.09(8) 1_455 . ? O8 La1 O11 89.90(9) 2_566 . ? O1 La1 O11 77.89(8) . . ? O9 La1 O11 76.67(8) . . ? O7 La1 O4 79.94(7) 1_455 2_556 ? O8 La1 O4 76.68(8) 2_566 2_556 ? O1 La1 O4 91.18(7) . 2_556 ? O9 La1 O4 69.22(7) . 2_556 ? O11 La1 O4 145.88(7) . 2_556 ? O7 La1 O5 76.96(7) 1_455 2_556 ? O8 La1 O5 147.70(7) 2_566 2_556 ? O1 La1 O5 71.51(7) . 2_556 ? O9 La1 O5 142.22(7) . 2_556 ? O11 La1 O5 83.81(8) . 2_556 ? O4 La1 O5 123.53(7) 2_556 2_556 ? O7 La1 N1 68.08(7) 1_455 2_556 ? O8 La1 N1 132.61(7) 2_566 2_556 ? O1 La1 N1 68.61(7) . 2_556 ? O9 La1 N1 115.49(8) . 2_556 ? O11 La1 N1 137.45(8) . 2_556 ? O4 La1 N1 62.13(7) 2_556 2_556 ? O5 La1 N1 61.49(7) 2_556 2_556 ? O7 La1 O10 66.96(7) 1_455 . ? O8 La1 O10 72.40(8) 2_566 . ? O1 La1 O10 132.05(7) . . ? O9 La1 O10 120.86(7) . . ? O11 La1 O10 63.88(8) . . ? O4 La1 O10 136.60(7) 2_556 . ? O5 La1 O10 76.42(7) 2_556 . ? N1 La1 O10 123.48(7) 2_556 . ? C1 O1 La1 147.6(2) . . ? C1 O2 H2 111(3) . . ? C7 O4 La1 126.49(19) . 2_556 ? C8 O5 La1 125.80(19) . 2_556 ? C9 O7 La1 142.82(19) . 1_655 ? C9 O8 La1 140.8(2) . 2_566 ? La1 O9 H9A 124(2) . . ? La1 O9 H9B 119(2) . . ? H9A O9 H9B 116.2(18) . . ? La1 O10 H10A 93(2) . . ? La1 O10 H10B 128(2) . . ? H10A O10 H10B 115.1(17) . . ? La1 O11 H11B 103.5 . . ? La1 O11 H11A 133.8 . . ? H11B O11 H11A 103.7 . . ? C6 N1 C5 121.0(2) . . ? C6 N1 La1 118.63(18) . 2_556 ? C5 N1 La1 120.08(18) . 2_556 ? O1 C1 O2 122.0(3) . . ? O1 C1 C2 123.8(3) . . ? O2 C1 C2 114.0(3) . . ? C6 C2 C3 118.2(3) . . ? C6 C2 C1 122.0(3) . . ? C3 C2 C1 119.6(2) . . ? C2 C3 C4 121.1(3) . . ? C2 C3 H3 119.4 . . ? C4 C3 H3 119.4 . . ? C5 C4 C3 116.9(3) . . ? C5 C4 C9 124.2(3) . . ? C3 C4 C9 118.7(3) . . ? N1 C5 C4 122.0(3) . . ? N1 C5 C8 116.1(2) . . ? C4 C5 C8 121.9(3) . . ? N1 C6 C2 120.6(3) . . ? N1 C6 C7 116.9(2) . . ? C2 C6 C7 122.4(3) . . ? O3 C7 O4 126.2(3) . . ? O3 C7 C6 118.3(3) . . ? O4 C7 C6 115.5(3) . . ? O6 C8 O5 125.4(3) . . ? O6 C8 C5 118.9(3) . . ? O5 C8 C5 115.7(3) . . ? O8 C9 O7 122.9(3) . . ? O8 C9 C4 114.5(2) . . ? O7 C9 C4 122.4(2) . . ? H12A O12 H12B 118.7(19) . . ? 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 O1 C1 78.0(4) 1_455 . . . ? O8 La1 O1 C1 -70.3(4) 2_566 . . . ? O9 La1 O1 C1 -66.8(4) . . . . ? O11 La1 O1 C1 -146.4(4) . . . . ? O4 La1 O1 C1 1.0(4) 2_556 . . . ? O5 La1 O1 C1 126.1(4) 2_556 . . . ? N1 La1 O1 C1 60.3(4) 2_556 . . . ? O10 La1 O1 C1 176.7(3) . . . . ? La1 O1 C1 O2 172.2(2) . . . . ? La1 O1 C1 C2 -3.0(5) . . . . ? O1 C1 C2 C6 -107.5(3) . . . . ? O2 C1 C2 C6 77.0(3) . . . . ? O1 C1 C2 C3 68.2(4) . . . . ? O2 C1 C2 C3 -107.3(3) . . . . ? C6 C2 C3 C4 -0.4(4) . . . . ? C1 C2 C3 C4 -176.2(2) . . . . ? C2 C3 C4 C5 0.3(4) . . . . ? C2 C3 C4 C9 176.6(2) . . . . ? C6 N1 C5 C4 -1.0(4) . . . . ? La1 N1 C5 C4 -175.34(19) 2_556 . . . ? C6 N1 C5 C8 179.0(2) . . . . ? La1 N1 C5 C8 4.7(3) 2_556 . . . ? C3 C4 C5 N1 0.5(4) . . . . ? C9 C4 C5 N1 -175.6(2) . . . . ? C3 C4 C5 C8 -179.6(2) . . . . ? C9 C4 C5 C8 4.3(4) . . . . ? C5 N1 C6 C2 0.9(4) . . . . ? La1 N1 C6 C2 175.25(19) 2_556 . . . ? C5 N1 C6 C7 -179.3(2) . . . . ? La1 N1 C6 C7 -5.0(3) 2_556 . . . ? C3 C2 C6 N1 -0.1(4) . . . . ? C1 C2 C6 N1 175.5(2) . . . . ? C3 C2 C6 C7 -179.9(2) . . . . ? C1 C2 C6 C7 -4.2(4) . . . . ? La1 O4 C7 O3 175.9(2) 2_556 . . . ? La1 O4 C7 C6 -4.3(3) 2_556 . . . ? N1 C6 C7 O3 -174.2(3) . . . . ? C2 C6 C7 O3 5.6(4) . . . . ? N1 C6 C7 O4 6.0(4) . . . . ? C2 C6 C7 O4 -174.2(3) . . . . ? La1 O5 C8 O6 -170.7(2) 2_556 . . . ? La1 O5 C8 C5 10.6(3) 2_556 . . . ? N1 C5 C8 O6 171.6(3) . . . . ? C4 C5 C8 O6 -8.3(4) . . . . ? N1 C5 C8 O5 -9.6(4) . . . . ? C4 C5 C8 O5 170.5(2) . . . . ? La1 O8 C9 O7 -5.2(5) 2_566 . . . ? La1 O8 C9 C4 170.8(2) 2_566 . . . ? La1 O7 C9 O8 113.1(3) 1_655 . . . ? La1 O7 C9 C4 -62.6(4) 1_655 . . . ? C5 C4 C9 O8 103.2(3) . . . . ? C3 C4 C9 O8 -72.9(3) . . . . ? C5 C4 C9 O7 -80.8(4) . . . . ? C3 C4 C9 O7 103.1(3) . . . . ? _diffrn_measured_fraction_theta_max 0.850 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 0.999 _refine_diff_density_max 1.363 _refine_diff_density_min -0.864 _refine_diff_density_rms 0.151 # Attachment '- complex 5.cif' data_m091223i _database_code_depnum_ccdc_archive 'CCDC 769000' #TrackingRef '- complex 5.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C9 H10 N O12 Tb' _chemical_formula_weight 483.10 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' 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 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 8.690(6) _cell_length_b 8.933(6) _cell_length_c 9.369(6) _cell_angle_alpha 77.65(3) _cell_angle_beta 80.88(2) _cell_angle_gamma 71.042(19) _cell_volume 668.8(7) _cell_formula_units_Z 2 _cell_measurement_temperature 113(2) _cell_measurement_reflns_used 2892 _cell_measurement_theta_min 2.2 _cell_measurement_theta_max 27.9 _exptl_crystal_description Prism _exptl_crystal_colour Colorless _exptl_crystal_size_max 0.08 _exptl_crystal_size_mid 0.06 _exptl_crystal_size_min 0.04 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 2.399 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 464 _exptl_absorpt_coefficient_mu 5.358 _exptl_absorpt_correction_type MULTI-SCAN _exptl_absorpt_correction_T_min 0.6738 _exptl_absorpt_correction_T_max 0.8142 _exptl_absorpt_process_details CrystalClear _exptl_special_details ; ? ; _diffrn_ambient_temperature 113(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'rotating anode' _diffrn_radiation_monochromator multilayer _diffrn_measurement_device_type 'Rigaku Saturn CCD area detector' _diffrn_measurement_method '\w and \f scans' _diffrn_detector_area_resol_mean 14.63 _diffrn_standards_number 0 _diffrn_standards_interval_count 0 _diffrn_standards_interval_time 0 _diffrn_standards_decay_% 0 _diffrn_reflns_number 6694 _diffrn_reflns_av_R_equivalents 0.0514 _diffrn_reflns_av_sigmaI/netI 0.0947 _diffrn_reflns_limit_h_min -11 _diffrn_reflns_limit_h_max 11 _diffrn_reflns_limit_k_min -11 _diffrn_reflns_limit_k_max 11 _diffrn_reflns_limit_l_min -11 _diffrn_reflns_limit_l_max 12 _diffrn_reflns_theta_min 2.24 _diffrn_reflns_theta_max 27.85 _reflns_number_total 3118 _reflns_number_gt 2616 _reflns_threshold_expression >2sigma(I) _computing_data_collection CrystalClear _computing_cell_refinement CrystalClear _computing_data_reduction CrystalClear _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'CrystalStructure 3.8' _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^)+(0.0722P)^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 SHELXL _refine_ls_extinction_coef 0.0044(12) _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_number_reflns 3118 _refine_ls_number_parameters 210 _refine_ls_number_restraints 24 _refine_ls_R_factor_all 0.0467 _refine_ls_R_factor_gt 0.0424 _refine_ls_wR_factor_ref 0.1312 _refine_ls_wR_factor_gt 0.1301 _refine_ls_goodness_of_fit_ref 1.036 _refine_ls_restrained_S_all 1.032 _refine_ls_shift/su_max 0.003 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group Tb1 Tb 0.14558(4) 0.33512(4) 0.66792(4) 0.00777(17) Uani 1 1 d . . . O1 O 0.1897(6) 0.2114(7) 0.4537(6) 0.0101(12) Uani 1 1 d . . . O2 O 0.3571(7) 0.0933(7) 0.2729(7) 0.0135(12) Uani 1 1 d . . . O3 O 0.7239(7) -0.0661(7) 0.2344(6) 0.0116(12) Uani 1 1 d . . . O4 O 0.6543(8) 0.1763(7) 0.0951(6) 0.0146(13) Uani 1 1 d . . . H4 H 0.5637 0.1886 0.0660 0.022 Uiso 1 1 calc R . . O5 O 0.8707(6) 0.4417(7) 0.5280(6) 0.0102(12) Uani 1 1 d . . . O6 O 0.9254(7) 0.2109(7) 0.6791(6) 0.0130(12) Uani 1 1 d . . . O7 O 0.5843(7) 0.4293(8) 0.7806(7) 0.0153(13) Uani 1 1 d . . . O8 O 0.3368(7) 0.4026(7) 0.7732(6) 0.0123(12) Uani 1 1 d . . . O9 O -0.0148(7) 0.5743(7) 0.7574(6) 0.0126(12) Uani 1 1 d . . . H9A H -0.0629 0.6364 0.6664 0.015 Uiso 1 1 d R . . H9B H -0.0957 0.5845 0.8228 0.015 Uiso 1 1 d R . . O10 O 0.0532(7) 0.2758(7) 0.9217(6) 0.0140(12) Uani 1 1 d . . . H10A H -0.0361 0.3416 0.9493 0.017 Uiso 1 1 d R . . H10B H 0.1223 0.2308 0.9844 0.017 Uiso 1 1 d R . . N1 N 0.4304(8) 0.2726(8) 0.5418(7) 0.0092(14) Uani 1 1 d . . . C1 C 0.3288(9) 0.1633(10) 0.3773(9) 0.0100(16) Uani 1 1 d . . . C2 C 0.4692(10) 0.2012(10) 0.4242(8) 0.0089(16) Uani 1 1 d . . . C3 C 0.6244(10) 0.1639(10) 0.3520(9) 0.0094(16) Uani 1 1 d U . . C4 C 0.7458(10) 0.1994(9) 0.4054(9) 0.0099(16) Uani 1 1 d . . . H4A H 0.8542 0.1734 0.3587 0.012 Uiso 1 1 calc R . . C5 C 0.7066(10) 0.2744(10) 0.5297(9) 0.0091(16) Uani 1 1 d . . . C6 C 0.5459(10) 0.3081(9) 0.5945(9) 0.0083(16) Uani 1 1 d U . . C7 C 0.4883(10) 0.3864(10) 0.7286(9) 0.0095(16) Uani 1 1 d U . . C8 C 0.6683(9) 0.0804(10) 0.2213(9) 0.0086(16) Uani 1 1 d . . . C9 C 0.8397(9) 0.3131(10) 0.5858(8) 0.0071(15) Uani 1 1 d U . . O11 O 0.2352(7) 0.5080(7) 0.0346(6) 0.0144(13) Uani 1 1 d . . . H11A H 0.3127 0.5198 0.0719 0.017 Uiso 1 1 d R . . H11B H 0.2470 0.5209 -0.0609 0.017 Uiso 1 1 d R . . O12 O 0.2033(7) 0.9867(8) 0.1101(6) 0.0151(13) Uani 1 1 d . . . H12A H 0.1684 0.9288 0.1842 0.018 Uiso 1 1 d R . . H12B H 0.1057 1.0094 0.0443 0.018 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 0.0068(2) 0.0071(2) 0.0094(2) -0.00238(14) 0.00040(14) -0.00200(15) O1 0.006(3) 0.013(3) 0.010(3) -0.002(2) 0.000(2) -0.001(2) O2 0.013(3) 0.013(3) 0.019(3) -0.011(3) 0.000(2) -0.005(2) O3 0.011(3) 0.008(3) 0.014(3) -0.003(2) -0.002(2) 0.000(2) O4 0.022(3) 0.012(3) 0.009(3) 0.002(2) -0.003(2) -0.006(3) O5 0.009(3) 0.007(3) 0.016(3) -0.003(2) 0.001(2) -0.004(2) O6 0.011(3) 0.016(3) 0.012(3) 0.001(2) -0.002(2) -0.005(2) O7 0.012(3) 0.022(3) 0.017(3) -0.010(3) -0.001(2) -0.008(3) O8 0.008(3) 0.017(3) 0.012(3) -0.006(2) 0.002(2) -0.003(2) O9 0.011(3) 0.012(3) 0.013(3) -0.005(2) 0.000(2) 0.000(2) O10 0.015(3) 0.012(3) 0.013(3) -0.006(2) -0.001(2) 0.001(2) N1 0.009(3) 0.013(4) 0.008(3) -0.002(3) -0.002(3) -0.007(3) C1 0.007(4) 0.013(4) 0.010(4) 0.000(3) -0.002(3) -0.004(3) C2 0.010(4) 0.010(4) 0.007(4) 0.001(3) -0.002(3) -0.003(3) C3 0.011(4) 0.004(3) 0.010(4) 0.000(3) -0.001(3) 0.000(3) C4 0.010(4) 0.005(4) 0.013(4) -0.003(3) 0.001(3) 0.000(3) C5 0.008(4) 0.007(4) 0.012(4) -0.001(3) -0.002(3) -0.003(3) C6 0.012(4) 0.002(3) 0.010(4) -0.001(3) -0.001(3) -0.001(3) C7 0.010(4) 0.005(4) 0.012(4) -0.001(3) -0.003(3) 0.001(3) C8 0.005(4) 0.012(4) 0.010(4) -0.004(3) 0.001(3) -0.004(3) C9 0.004(3) 0.009(4) 0.009(3) -0.006(3) 0.003(3) -0.003(3) O11 0.012(3) 0.017(3) 0.015(3) -0.009(3) 0.001(2) -0.004(2) O12 0.019(3) 0.018(3) 0.010(3) 0.001(2) -0.002(2) -0.010(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 2.348(6) 2_656 ? Tb1 O8 2.350(6) . ? Tb1 O9 2.382(6) . ? Tb1 O5 2.387(6) 2_666 ? Tb1 O10 2.390(6) . ? Tb1 O1 2.414(6) . ? Tb1 O6 2.484(6) 1_455 ? Tb1 N1 2.508(7) . ? Tb1 O5 2.704(6) 1_455 ? Tb1 C9 2.958(8) 1_455 ? O1 C1 1.295(9) . ? O2 C1 1.222(10) . ? O3 C8 1.225(10) . ? O3 Tb1 2.348(6) 2_656 ? O4 C8 1.301(10) . ? O4 H4 0.8400 . ? O5 C9 1.255(9) . ? O5 Tb1 2.387(6) 2_666 ? O5 Tb1 2.704(6) 1_655 ? O6 C9 1.255(10) . ? O6 Tb1 2.484(6) 1_655 ? O7 C7 1.224(10) . ? O8 C7 1.286(9) . ? O9 H9A 0.9845 . ? O9 H9B 0.8503 . ? O10 H10A 0.8486 . ? O10 H10B 0.8491 . ? N1 C2 1.333(10) . ? N1 C6 1.335(10) . ? C1 C2 1.516(11) . ? C2 C3 1.379(11) . ? C3 C4 1.385(11) . ? C3 C8 1.503(11) . ? C4 C5 1.408(11) . ? C4 H4A 0.9500 . ? C5 C6 1.396(11) . ? C5 C9 1.504(11) . ? C6 C7 1.506(11) . ? C9 Tb1 2.958(8) 1_655 ? O11 H11A 0.8502 . ? O11 H11B 0.8706 . ? O12 H12A 0.8501 . ? O12 H12B 1.0681 . ? 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 O8 87.0(2) 2_656 . ? O3 Tb1 O9 137.7(2) 2_656 . ? O8 Tb1 O9 77.2(2) . . ? O3 Tb1 O5 148.95(19) 2_656 2_666 ? O8 Tb1 O5 91.2(2) . 2_666 ? O9 Tb1 O5 71.3(2) . 2_666 ? O3 Tb1 O10 69.6(2) 2_656 . ? O8 Tb1 O10 80.3(2) . . ? O9 Tb1 O10 69.2(2) . . ? O5 Tb1 O10 140.5(2) 2_666 . ? O3 Tb1 O1 79.2(2) 2_656 . ? O8 Tb1 O1 127.97(18) . . ? O9 Tb1 O1 140.5(2) . . ? O5 Tb1 O1 77.6(2) 2_666 . ? O10 Tb1 O1 136.8(2) . . ? O3 Tb1 O6 78.7(2) 2_656 1_455 ? O8 Tb1 O6 153.2(2) . 1_455 ? O9 Tb1 O6 98.5(2) . 1_455 ? O5 Tb1 O6 112.70(19) 2_666 1_455 ? O10 Tb1 O6 73.6(2) . 1_455 ? O1 Tb1 O6 71.54(19) . 1_455 ? O3 Tb1 N1 74.5(2) 2_656 . ? O8 Tb1 N1 63.8(2) . . ? O9 Tb1 N1 128.4(2) . . ? O5 Tb1 N1 76.9(2) 2_666 . ? O10 Tb1 N1 129.9(2) . . ? O1 Tb1 N1 64.1(2) . . ? O6 Tb1 N1 131.4(2) 1_455 . ? O3 Tb1 O5 125.66(18) 2_656 1_455 ? O8 Tb1 O5 147.01(19) . 1_455 ? O9 Tb1 O5 74.52(18) . 1_455 ? O5 Tb1 O5 63.9(2) 2_666 1_455 ? O10 Tb1 O5 104.73(19) . 1_455 ? O1 Tb1 O5 70.10(18) . 1_455 ? O6 Tb1 O5 49.78(18) 1_455 1_455 ? N1 Tb1 O5 124.54(19) . 1_455 ? O3 Tb1 C9 101.7(2) 2_656 1_455 ? O8 Tb1 C9 164.0(2) . 1_455 ? O9 Tb1 C9 87.4(2) . 1_455 ? O5 Tb1 C9 88.2(2) 2_666 1_455 ? O10 Tb1 C9 90.0(2) . 1_455 ? O1 Tb1 C9 67.46(19) . 1_455 ? O6 Tb1 C9 24.8(2) 1_455 1_455 ? N1 Tb1 C9 131.3(2) . 1_455 ? O5 Tb1 C9 25.09(19) 1_455 1_455 ? C1 O1 Tb1 125.4(5) . . ? C8 O3 Tb1 160.9(6) . 2_656 ? C8 O4 H4 109.5 . . ? C9 O5 Tb1 151.0(5) . 2_666 ? C9 O5 Tb1 88.9(5) . 1_655 ? Tb1 O5 Tb1 116.1(2) 2_666 1_655 ? C9 O6 Tb1 99.3(5) . 1_655 ? C7 O8 Tb1 128.4(5) . . ? Tb1 O9 H9A 98.7 . . ? Tb1 O9 H9B 127.3 . . ? H9A O9 H9B 104.3 . . ? Tb1 O10 H10A 114.8 . . ? Tb1 O10 H10B 119.9 . . ? H10A O10 H10B 117.3 . . ? C2 N1 C6 119.3(7) . . ? C2 N1 Tb1 120.9(5) . . ? C6 N1 Tb1 119.8(5) . . ? O2 C1 O1 127.2(7) . . ? O2 C1 C2 117.8(7) . . ? O1 C1 C2 115.1(7) . . ? N1 C2 C3 122.8(7) . . ? N1 C2 C1 114.3(7) . . ? C3 C2 C1 122.9(7) . . ? C2 C3 C4 118.7(7) . . ? C2 C3 C8 122.6(7) . . ? C4 C3 C8 118.7(7) . . ? C3 C4 C5 119.1(7) . . ? C3 C4 H4A 120.4 . . ? C5 C4 H4A 120.4 . . ? C6 C5 C4 117.9(7) . . ? C6 C5 C9 123.6(7) . . ? C4 C5 C9 118.5(7) . . ? N1 C6 C5 122.2(7) . . ? N1 C6 C7 114.6(7) . . ? C5 C6 C7 123.2(7) . . ? O7 C7 O8 127.6(8) . . ? O7 C7 C6 119.0(7) . . ? O8 C7 C6 113.4(7) . . ? O3 C8 O4 123.4(7) . . ? O3 C8 C3 121.7(7) . . ? O4 C8 C3 114.7(7) . . ? O5 C9 O6 121.8(7) . . ? O5 C9 C5 118.4(7) . . ? O6 C9 C5 119.5(7) . . ? O5 C9 Tb1 66.1(4) . 1_655 ? O6 C9 Tb1 56.0(4) . 1_655 ? C5 C9 Tb1 168.5(5) . 1_655 ? H11A O11 H11B 114.3 . . ? H12A O12 H12B 97.5 . . ? 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 O3 Tb1 O1 C1 -74.6(6) 2_656 . . . ? O8 Tb1 O1 C1 2.9(7) . . . . ? O9 Tb1 O1 C1 123.2(6) . . . . ? O5 Tb1 O1 C1 84.6(6) 2_666 . . . ? O10 Tb1 O1 C1 -118.5(6) . . . . ? O6 Tb1 O1 C1 -156.1(7) 1_455 . . . ? N1 Tb1 O1 C1 3.3(6) . . . . ? O5 Tb1 O1 C1 151.0(7) 1_455 . . . ? C9 Tb1 O1 C1 177.8(7) 1_455 . . . ? O3 Tb1 O8 C7 75.8(7) 2_656 . . . ? O9 Tb1 O8 C7 -143.7(7) . . . . ? O5 Tb1 O8 C7 -73.2(7) 2_666 . . . ? O10 Tb1 O8 C7 145.6(7) . . . . ? O1 Tb1 O8 C7 2.0(8) . . . . ? O6 Tb1 O8 C7 132.9(7) 1_455 . . . ? N1 Tb1 O8 C7 1.6(6) . . . . ? O5 Tb1 O8 C7 -112.2(7) 1_455 . . . ? C9 Tb1 O8 C7 -160.8(7) 1_455 . . . ? O3 Tb1 N1 C2 84.0(6) 2_656 . . . ? O8 Tb1 N1 C2 178.3(7) . . . . ? O9 Tb1 N1 C2 -136.6(6) . . . . ? O5 Tb1 N1 C2 -83.8(6) 2_666 . . . ? O10 Tb1 N1 C2 129.2(6) . . . . ? O1 Tb1 N1 C2 -1.4(6) . . . . ? O6 Tb1 N1 C2 25.0(7) 1_455 . . . ? O5 Tb1 N1 C2 -39.0(7) 1_455 . . . ? C9 Tb1 N1 C2 -8.1(7) 1_455 . . . ? O3 Tb1 N1 C6 -94.6(6) 2_656 . . . ? O8 Tb1 N1 C6 -0.3(6) . . . . ? O9 Tb1 N1 C6 44.8(7) . . . . ? O5 Tb1 N1 C6 97.6(6) 2_666 . . . ? O10 Tb1 N1 C6 -49.4(7) . . . . ? O1 Tb1 N1 C6 180.0(7) . . . . ? O6 Tb1 N1 C6 -153.6(5) 1_455 . . . ? O5 Tb1 N1 C6 142.4(5) 1_455 . . . ? C9 Tb1 N1 C6 173.3(5) 1_455 . . . ? Tb1 O1 C1 O2 176.1(6) . . . . ? Tb1 O1 C1 C2 -4.5(10) . . . . ? C6 N1 C2 C3 -1.0(12) . . . . ? Tb1 N1 C2 C3 -179.7(6) . . . . ? C6 N1 C2 C1 178.5(7) . . . . ? Tb1 N1 C2 C1 -0.1(9) . . . . ? O2 C1 C2 N1 -177.8(8) . . . . ? O1 C1 C2 N1 2.8(11) . . . . ? O2 C1 C2 C3 1.8(12) . . . . ? O1 C1 C2 C3 -177.7(8) . . . . ? N1 C2 C3 C4 1.2(12) . . . . ? C1 C2 C3 C4 -178.3(7) . . . . ? N1 C2 C3 C8 178.8(8) . . . . ? C1 C2 C3 C8 -0.8(12) . . . . ? C2 C3 C4 C5 -1.0(12) . . . . ? C8 C3 C4 C5 -178.6(7) . . . . ? C3 C4 C5 C6 0.7(12) . . . . ? C3 C4 C5 C9 -179.7(7) . . . . ? C2 N1 C6 C5 0.7(12) . . . . ? Tb1 N1 C6 C5 179.3(6) . . . . ? C2 N1 C6 C7 -179.2(7) . . . . ? Tb1 N1 C6 C7 -0.6(9) . . . . ? C4 C5 C6 N1 -0.5(12) . . . . ? C9 C5 C6 N1 179.9(7) . . . . ? C4 C5 C6 C7 179.4(7) . . . . ? C9 C5 C6 C7 -0.3(13) . . . . ? Tb1 O8 C7 O7 176.1(6) . . . . ? Tb1 O8 C7 C6 -2.4(10) . . . . ? N1 C6 C7 O7 -176.9(7) . . . . ? C5 C6 C7 O7 3.2(12) . . . . ? N1 C6 C7 O8 1.7(10) . . . . ? C5 C6 C7 O8 -178.1(8) . . . . ? Tb1 O3 C8 O4 151.3(12) 2_656 . . . ? Tb1 O3 C8 C3 -23(2) 2_656 . . . ? C2 C3 C8 O3 -92.6(10) . . . . ? C4 C3 C8 O3 84.9(10) . . . . ? C2 C3 C8 O4 92.4(9) . . . . ? C4 C3 C8 O4 -90.1(9) . . . . ? Tb1 O5 C9 O6 156.4(7) 2_666 . . . ? Tb1 O5 C9 O6 5.5(7) 1_655 . . . ? Tb1 O5 C9 C5 -17.3(14) 2_666 . . . ? Tb1 O5 C9 C5 -168.2(6) 1_655 . . . ? Tb1 O5 C9 Tb1 150.8(10) 2_666 . . 1_655 ? Tb1 O6 C9 O5 -6.1(8) 1_655 . . . ? Tb1 O6 C9 C5 167.5(6) 1_655 . . . ? C6 C5 C9 O5 -96.0(10) . . . . ? C4 C5 C9 O5 84.3(10) . . . . ? C6 C5 C9 O6 90.2(10) . . . . ? C4 C5 C9 O6 -89.5(9) . . . . ? C6 C5 C9 Tb1 154(2) . . . 1_655 ? C4 C5 C9 Tb1 -26(3) . . . 1_655 ? loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA _geom_hbond_site_symmetry_A O4 H4 O2 0.84 2.63 3.058(8) 113.4 . O9 H9A O1 0.98 1.76 2.707(8) 160.5 2_566 O9 H9B O11 0.85 1.90 2.669(8) 150.1 2_566 O10 H10A O11 0.85 1.82 2.655(8) 167.2 2_566 O10 H10B O12 0.85 2.19 2.841(9) 133.3 1_546 O11 H11A O7 0.85 1.96 2.760(9) 156.3 2_666 O12 H12A O6 0.85 1.87 2.713(8) 169.0 2_666 O11 H11B O8 0.87 1.98 2.725(8) 142.7 1_554 _diffrn_measured_fraction_theta_max 0.979 _diffrn_reflns_theta_full 27.85 _diffrn_measured_fraction_theta_full 0.979 _refine_diff_density_max 4.683 _refine_diff_density_min -2.532 _refine_diff_density_rms 0.386 # Attachment '- complex 4.cif' data_shelx _database_code_depnum_ccdc_archive 'CCDC 769001' #TrackingRef '- complex 4.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C9 H10 Eu N O12' _chemical_formula_weight 476.14 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' Eu Eu -0.1578 3.6682 '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 8.718(3) _cell_length_b 8.963(3) _cell_length_c 9.390(4) _cell_angle_alpha 77.884(16) _cell_angle_beta 80.880(15) _cell_angle_gamma 71.220(15) _cell_volume 675.9(4) _cell_formula_units_Z 2 _cell_measurement_temperature 113(2) _cell_measurement_reflns_used 2457 _cell_measurement_theta_min 2.2 _cell_measurement_theta_max 27.9 _exptl_crystal_description Prism _exptl_crystal_colour Colorless _exptl_crystal_size_max 0.10 _exptl_crystal_size_mid 0.06 _exptl_crystal_size_min 0.06 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 2.340 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 460 _exptl_absorpt_coefficient_mu 4.711 _exptl_absorpt_correction_type MULTI-SCAN _exptl_absorpt_correction_T_min 0.6502 _exptl_absorpt_correction_T_max 0.7653 _exptl_absorpt_process_details CrystalClear _exptl_special_details ; ? ; _diffrn_ambient_temperature 113(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 'Rigaku Saturn CCD area detector' _diffrn_measurement_method '\w and \f scans' _diffrn_detector_area_resol_mean 14.63 _diffrn_standards_number 0 _diffrn_standards_interval_count 0 _diffrn_standards_interval_time 0 _diffrn_standards_decay_% 0 _diffrn_reflns_number 7031 _diffrn_reflns_av_R_equivalents 0.0762 _diffrn_reflns_av_sigmaI/netI 0.1491 _diffrn_reflns_limit_h_min -11 _diffrn_reflns_limit_h_max 11 _diffrn_reflns_limit_k_min -11 _diffrn_reflns_limit_k_max 9 _diffrn_reflns_limit_l_min -12 _diffrn_reflns_limit_l_max 12 _diffrn_reflns_theta_min 2.23 _diffrn_reflns_theta_max 27.84 _reflns_number_total 3176 _reflns_number_gt 2254 _reflns_threshold_expression >2sigma(I) _computing_data_collection CrystalClear _computing_cell_refinement CrystalClear _computing_data_reduction CrystalClear _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'CrystalStructure 3.8' _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^)+(0.0331P)^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 3176 _refine_ls_number_parameters 209 _refine_ls_number_restraints 66 _refine_ls_R_factor_all 0.0603 _refine_ls_R_factor_gt 0.0474 _refine_ls_wR_factor_ref 0.1091 _refine_ls_wR_factor_gt 0.1047 _refine_ls_goodness_of_fit_ref 0.939 _refine_ls_restrained_S_all 0.932 _refine_ls_shift/su_max 0.004 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group Eu1 Eu 0.14484(5) 0.33622(5) 0.66740(5) 0.00944(14) Uani 1 1 d . . . O1 O 0.1926(6) 0.2102(6) 0.4500(6) 0.0108(13) Uani 1 1 d . . . O2 O 0.3594(7) 0.0947(7) 0.2721(6) 0.0148(14) Uani 1 1 d . . . O3 O 0.7233(6) -0.0650(6) 0.2330(6) 0.0117(13) Uani 1 1 d . . . O4 O 0.6560(7) 0.1758(6) 0.0938(6) 0.0169(14) Uani 1 1 d . . . H4 H 0.7010 0.1232 0.0263 0.025 Uiso 1 1 calc R . . O5 O 0.8732(6) 0.4379(6) 0.5289(6) 0.0119(13) Uani 1 1 d . . . O6 O 0.9267(6) 0.2068(6) 0.6783(6) 0.0120(13) Uani 1 1 d . . . O7 O 0.5884(7) 0.4255(7) 0.7796(7) 0.0191(14) Uani 1 1 d . . . O8 O 0.3408(6) 0.4028(6) 0.7716(6) 0.0090(12) Uani 1 1 d U . . O9 O -0.0161(6) 0.5786(6) 0.7611(6) 0.0112(13) Uani 1 1 d . . . H9A H -0.0642 0.6408 0.6701 0.013 Uiso 1 1 d R . . H9B H -0.0969 0.5888 0.8265 0.013 Uiso 1 1 d R . . O10 O 0.0504(7) 0.2717(6) 0.9213(6) 0.0156(13) Uani 1 1 d . . . H10A H -0.0389 0.3375 0.9489 0.019 Uiso 1 1 d R . . H10B H 0.1195 0.2267 0.9840 0.019 Uiso 1 1 d R . . N1 N 0.4326(7) 0.2718(7) 0.5408(7) 0.0069(14) Uani 1 1 d U . . C1 C 0.3284(10) 0.1663(9) 0.3785(9) 0.0110(18) Uani 1 1 d U . . C2 C 0.4699(10) 0.2004(10) 0.4244(9) 0.0117(18) Uani 1 1 d U . . C3 C 0.6252(9) 0.1627(9) 0.3490(9) 0.0092(17) Uani 1 1 d U . . C4 C 0.7457(9) 0.1989(9) 0.4057(8) 0.0061(16) Uani 1 1 d U . . H4A H 0.8542 0.1733 0.3603 0.007 Uiso 1 1 calc R . . C5 C 0.7063(9) 0.2715(9) 0.5271(8) 0.0087(17) Uani 1 1 d U . . C6 C 0.5489(9) 0.3076(9) 0.5939(9) 0.0108(18) Uani 1 1 d U . . C7 C 0.4896(9) 0.3871(9) 0.7289(8) 0.0084(17) Uani 1 1 d U . . C8 C 0.6698(9) 0.0800(10) 0.2199(9) 0.0076(16) Uani 1 1 d U . . C9 C 0.8411(9) 0.3084(9) 0.5853(8) 0.0053(16) Uani 1 1 d U . . O11 O 0.2375(7) 0.5042(7) 0.0332(6) 0.0181(14) Uani 1 1 d . . . H11A H 0.3150 0.5160 0.0705 0.022 Uiso 1 1 d R . . H11B H 0.2493 0.5171 -0.0622 0.022 Uiso 1 1 d R . . O12 O 0.2026(6) 0.9924(6) 0.1115(6) 0.0127(13) Uani 1 1 d . . . H12A H 0.1678 0.9345 0.1856 0.015 Uiso 1 1 d R . . H12B H 0.1051 1.0151 0.0457 0.015 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 0.0065(2) 0.0106(3) 0.0131(2) -0.00259(18) -0.00216(16) -0.00428(18) O1 0.005(3) 0.008(3) 0.020(3) -0.004(3) -0.001(2) -0.001(2) O2 0.013(3) 0.016(3) 0.020(3) -0.014(3) -0.003(3) -0.003(3) O3 0.005(3) 0.003(3) 0.025(4) 0.005(3) -0.005(2) -0.002(2) O4 0.020(3) 0.012(3) 0.016(3) 0.000(3) -0.005(3) 0.000(3) O5 0.011(3) 0.009(3) 0.016(3) -0.001(3) -0.007(2) -0.002(3) O6 0.011(3) 0.008(3) 0.019(3) 0.004(3) -0.006(3) -0.008(3) O7 0.011(3) 0.022(4) 0.030(4) -0.010(3) -0.005(3) -0.006(3) O8 0.0094(14) 0.0101(15) 0.0085(15) -0.0030(9) -0.0017(9) -0.0031(10) O9 0.009(3) 0.017(3) 0.006(3) -0.008(3) 0.003(2) 0.000(3) O10 0.017(3) 0.018(3) 0.012(3) -0.007(3) -0.005(3) 0.000(3) N1 0.0070(16) 0.0073(16) 0.0071(16) -0.0015(10) -0.0014(9) -0.0024(10) C1 0.0110(19) 0.012(2) 0.011(2) -0.0022(10) -0.0019(10) -0.0036(11) C2 0.012(2) 0.011(2) 0.012(2) -0.0017(10) -0.0013(10) -0.0038(11) C3 0.0091(19) 0.0091(19) 0.0096(19) -0.0010(10) -0.0012(10) -0.0033(11) C4 0.0069(18) 0.0061(18) 0.0058(18) -0.0022(10) -0.0011(10) -0.0018(10) C5 0.0088(19) 0.0086(19) 0.0092(19) -0.0015(10) -0.0012(10) -0.0030(11) C6 0.0106(19) 0.011(2) 0.012(2) -0.0014(10) -0.0009(10) -0.0038(11) C7 0.0087(19) 0.0084(19) 0.0085(19) -0.0020(10) -0.0015(10) -0.0024(11) C8 0.0078(18) 0.0080(19) 0.0078(19) -0.0019(10) -0.0016(10) -0.0026(11) C9 0.0057(18) 0.0059(18) 0.0048(18) -0.0018(10) -0.0007(10) -0.0014(10) O11 0.015(3) 0.028(4) 0.016(3) -0.005(3) -0.006(3) -0.010(3) O12 0.015(3) 0.015(3) 0.010(3) -0.002(3) -0.004(2) -0.007(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 Eu1 O8 2.380(5) . ? Eu1 O3 2.386(5) 2_656 ? Eu1 O10 2.408(6) . ? Eu1 O5 2.417(6) 2_666 ? Eu1 O9 2.432(5) . ? Eu1 O1 2.452(5) . ? Eu1 O6 2.506(5) 1_455 ? Eu1 N1 2.540(6) . ? Eu1 O5 2.687(5) 1_455 ? Eu1 C9 2.971(7) 1_455 ? Eu1 Eu1 4.3300(16) 2_566 ? Eu1 H9A 2.7540 . ? O1 C1 1.252(9) . ? O2 C1 1.247(9) . ? O3 C8 1.218(9) . ? O3 Eu1 2.386(5) 2_656 ? O4 C8 1.306(9) . ? O4 H4 0.8400 . ? O5 C9 1.270(8) . ? O5 Eu1 2.417(6) 2_666 ? O5 Eu1 2.687(5) 1_655 ? O6 C9 1.259(9) . ? O6 Eu1 2.506(5) 1_655 ? O7 C7 1.215(8) . ? O8 C7 1.267(9) . ? O9 H9A 0.9896 . ? O9 H9B 0.8526 . ? O10 H10A 0.8522 . ? O10 H10B 0.8534 . ? N1 C2 1.326(9) . ? N1 C6 1.347(9) . ? C1 C2 1.506(10) . ? C2 C3 1.396(11) . ? C3 C4 1.401(9) . ? C3 C8 1.488(10) . ? C4 C5 1.373(10) . ? C4 H4A 0.9500 . ? C5 C6 1.381(11) . ? C5 C9 1.522(9) . ? C6 C7 1.522(10) . ? C9 Eu1 2.971(7) 1_655 ? O11 H11A 0.8523 . ? O11 H11B 0.8730 . ? O12 H12A 0.8535 . ? O12 H12B 1.0721 . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag O8 Eu1 O3 86.34(17) . 2_656 ? O8 Eu1 O10 81.94(17) . . ? O3 Eu1 O10 68.54(18) 2_656 . ? O8 Eu1 O5 91.19(17) . 2_666 ? O3 Eu1 O5 149.62(19) 2_656 2_666 ? O10 Eu1 O5 141.03(18) . 2_666 ? O8 Eu1 O9 77.39(17) . . ? O3 Eu1 O9 136.95(19) 2_656 . ? O10 Eu1 O9 69.86(18) . . ? O5 Eu1 O9 71.20(18) 2_666 . ? O8 Eu1 O1 126.57(17) . . ? O3 Eu1 O1 79.35(18) 2_656 . ? O10 Eu1 O1 135.72(17) . . ? O5 Eu1 O1 77.93(18) 2_666 . ? O9 Eu1 O1 141.43(18) . . ? O8 Eu1 O6 153.48(18) . 1_455 ? O3 Eu1 O6 77.98(17) 2_656 1_455 ? O10 Eu1 O6 72.49(17) . 1_455 ? O5 Eu1 O6 113.07(17) 2_666 1_455 ? O9 Eu1 O6 99.68(17) . 1_455 ? O1 Eu1 O6 71.60(17) . 1_455 ? O8 Eu1 N1 63.01(18) . . ? O3 Eu1 N1 74.23(19) 2_656 . ? O10 Eu1 N1 129.9(2) . . ? O5 Eu1 N1 77.70(19) 2_666 . ? O9 Eu1 N1 128.43(18) . . ? O1 Eu1 N1 63.56(17) . . ? O6 Eu1 N1 130.46(18) 1_455 . ? O8 Eu1 O5 148.01(17) . 1_455 ? O3 Eu1 O5 125.36(16) 2_656 1_455 ? O10 Eu1 O5 104.22(18) . 1_455 ? O5 Eu1 O5 64.03(19) 2_666 1_455 ? O9 Eu1 O5 75.59(16) . 1_455 ? O1 Eu1 O5 70.32(17) . 1_455 ? O6 Eu1 O5 49.99(17) 1_455 1_455 ? N1 Eu1 O5 124.73(18) . 1_455 ? O8 Eu1 C9 165.40(19) . 1_455 ? O3 Eu1 C9 101.12(19) 2_656 1_455 ? O10 Eu1 C9 89.08(19) . 1_455 ? O5 Eu1 C9 88.6(2) 2_666 1_455 ? O9 Eu1 C9 88.73(18) . 1_455 ? O1 Eu1 C9 67.59(18) . 1_455 ? O6 Eu1 C9 24.75(18) 1_455 1_455 ? N1 Eu1 C9 130.96(19) . 1_455 ? O5 Eu1 C9 25.30(18) 1_455 1_455 ? O8 Eu1 Eu1 122.55(13) . 2_566 ? O3 Eu1 Eu1 147.21(12) 2_656 2_566 ? O10 Eu1 Eu1 125.90(14) . 2_566 ? O5 Eu1 Eu1 33.91(12) 2_666 2_566 ? O9 Eu1 Eu1 70.48(13) . 2_566 ? O1 Eu1 Eu1 70.99(13) . 2_566 ? O6 Eu1 Eu1 79.61(13) 1_455 2_566 ? N1 Eu1 Eu1 103.57(15) . 2_566 ? O5 Eu1 Eu1 30.12(11) 1_455 2_566 ? C9 Eu1 Eu1 54.90(15) 1_455 2_566 ? O8 Eu1 H9A 90.2 . . ? O3 Eu1 H9A 156.2 2_656 . ? O10 Eu1 H9A 87.7 . . ? O5 Eu1 H9A 53.9 2_666 . ? O9 Eu1 H9A 20.8 . . ? O1 Eu1 H9A 120.7 . . ? O6 Eu1 H9A 95.6 1_455 . ? N1 Eu1 H9A 124.5 . . ? O5 Eu1 H9A 59.3 1_455 . ? C9 Eu1 H9A 77.9 1_455 . ? Eu1 Eu1 H9A 49.7 2_566 . ? C1 O1 Eu1 124.2(5) . . ? C8 O3 Eu1 160.5(5) . 2_656 ? C8 O4 H4 109.5 . . ? C9 O5 Eu1 150.3(5) . 2_666 ? C9 O5 Eu1 89.9(4) . 1_655 ? Eu1 O5 Eu1 115.97(19) 2_666 1_655 ? C9 O6 Eu1 98.8(4) . 1_655 ? C7 O8 Eu1 129.7(5) . . ? Eu1 O9 H9A 98.3 . . ? Eu1 O9 H9B 127.3 . . ? H9A O9 H9B 104.2 . . ? Eu1 O10 H10A 114.2 . . ? Eu1 O10 H10B 119.6 . . ? H10A O10 H10B 117.5 . . ? C2 N1 C6 119.7(7) . . ? C2 N1 Eu1 120.4(5) . . ? C6 N1 Eu1 119.9(5) . . ? O2 C1 O1 126.2(7) . . ? O2 C1 C2 115.9(7) . . ? O1 C1 C2 117.9(7) . . ? N1 C2 C3 123.4(7) . . ? N1 C2 C1 113.8(7) . . ? C3 C2 C1 122.8(7) . . ? C2 C3 C4 116.5(7) . . ? C2 C3 C8 124.0(7) . . ? C4 C3 C8 119.3(7) . . ? C5 C4 C3 119.7(7) . . ? C5 C4 H4A 120.2 . . ? C3 C4 H4A 120.2 . . ? C4 C5 C6 120.3(7) . . ? C4 C5 C9 118.0(7) . . ? C6 C5 C9 121.8(7) . . ? N1 C6 C5 120.4(7) . . ? N1 C6 C7 114.1(7) . . ? C5 C6 C7 125.5(7) . . ? O7 C7 O8 129.7(7) . . ? O7 C7 C6 117.0(7) . . ? O8 C7 C6 113.3(6) . . ? O3 C8 O4 123.7(7) . . ? O3 C8 C3 121.7(8) . . ? O4 C8 C3 114.5(7) . . ? O6 C9 O5 121.0(6) . . ? O6 C9 C5 120.5(7) . . ? O5 C9 C5 118.2(7) . . ? O6 C9 Eu1 56.5(4) . 1_655 ? O5 C9 Eu1 64.8(4) . 1_655 ? C5 C9 Eu1 169.5(5) . 1_655 ? H11A O11 H11B 114.2 . . ? H12A O12 H12B 97.6 . . ? 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 O8 Eu1 O1 C1 2.2(7) . . . . ? O3 Eu1 O1 C1 -75.1(6) 2_656 . . . ? O10 Eu1 O1 C1 -118.5(6) . . . . ? O5 Eu1 O1 C1 84.6(6) 2_666 . . . ? O9 Eu1 O1 C1 121.8(6) . . . . ? O6 Eu1 O1 C1 -155.8(7) 1_455 . . . ? N1 Eu1 O1 C1 2.5(6) . . . . ? O5 Eu1 O1 C1 151.1(7) 1_455 . . . ? C9 Eu1 O1 C1 178.1(7) 1_455 . . . ? Eu1 Eu1 O1 C1 119.1(6) 2_566 . . . ? O3 Eu1 O8 C7 76.0(7) 2_656 . . . ? O10 Eu1 O8 C7 144.8(7) . . . . ? O5 Eu1 O8 C7 -73.7(7) 2_666 . . . ? O9 Eu1 O8 C7 -144.1(7) . . . . ? O1 Eu1 O8 C7 2.1(8) . . . . ? O6 Eu1 O8 C7 129.4(7) 1_455 . . . ? N1 Eu1 O8 C7 1.8(6) . . . . ? O5 Eu1 O8 C7 -111.2(7) 1_455 . . . ? C9 Eu1 O8 C7 -162.6(8) 1_455 . . . ? Eu1 Eu1 O8 C7 -87.4(7) 2_566 . . . ? O8 Eu1 N1 C2 178.3(7) . . . . ? O3 Eu1 N1 C2 84.3(6) 2_656 . . . ? O10 Eu1 N1 C2 127.3(6) . . . . ? O5 Eu1 N1 C2 -84.0(6) 2_666 . . . ? O9 Eu1 N1 C2 -137.5(6) . . . . ? O1 Eu1 N1 C2 -1.5(6) . . . . ? O6 Eu1 N1 C2 26.0(7) 1_455 . . . ? O5 Eu1 N1 C2 -38.1(7) 1_455 . . . ? C9 Eu1 N1 C2 -6.9(7) 1_455 . . . ? Eu1 Eu1 N1 C2 -61.9(6) 2_566 . . . ? O8 Eu1 N1 C6 -0.5(5) . . . . ? O3 Eu1 N1 C6 -94.4(6) 2_656 . . . ? O10 Eu1 N1 C6 -51.4(6) . . . . ? O5 Eu1 N1 C6 97.3(6) 2_666 . . . ? O9 Eu1 N1 C6 43.7(7) . . . . ? O1 Eu1 N1 C6 179.8(6) . . . . ? O6 Eu1 N1 C6 -152.8(5) 1_455 . . . ? O5 Eu1 N1 C6 143.1(5) 1_455 . . . ? C9 Eu1 N1 C6 174.4(5) 1_455 . . . ? Eu1 Eu1 N1 C6 119.4(6) 2_566 . . . ? Eu1 O1 C1 O2 176.1(6) . . . . ? Eu1 O1 C1 C2 -3.2(10) . . . . ? C6 N1 C2 C3 -1.8(13) . . . . ? Eu1 N1 C2 C3 179.5(6) . . . . ? C6 N1 C2 C1 179.4(7) . . . . ? Eu1 N1 C2 C1 0.7(9) . . . . ? O2 C1 C2 N1 -177.9(7) . . . . ? O1 C1 C2 N1 1.5(11) . . . . ? O2 C1 C2 C3 3.3(12) . . . . ? O1 C1 C2 C3 -177.3(8) . . . . ? N1 C2 C3 C4 2.3(13) . . . . ? C1 C2 C3 C4 -179.0(7) . . . . ? N1 C2 C3 C8 178.9(8) . . . . ? C1 C2 C3 C8 -2.4(13) . . . . ? C2 C3 C4 C5 -1.6(12) . . . . ? C8 C3 C4 C5 -178.3(7) . . . . ? C3 C4 C5 C6 0.5(12) . . . . ? C3 C4 C5 C9 179.8(7) . . . . ? C2 N1 C6 C5 0.5(12) . . . . ? Eu1 N1 C6 C5 179.2(6) . . . . ? C2 N1 C6 C7 -179.2(7) . . . . ? Eu1 N1 C6 C7 -0.5(9) . . . . ? C4 C5 C6 N1 0.1(13) . . . . ? C9 C5 C6 N1 -179.2(7) . . . . ? C4 C5 C6 C7 179.8(8) . . . . ? C9 C5 C6 C7 0.5(13) . . . . ? Eu1 O8 C7 O7 177.5(6) . . . . ? Eu1 O8 C7 C6 -2.7(10) . . . . ? N1 C6 C7 O7 -178.4(7) . . . . ? C5 C6 C7 O7 1.9(13) . . . . ? N1 C6 C7 O8 1.8(11) . . . . ? C5 C6 C7 O8 -177.9(8) . . . . ? Eu1 O3 C8 O4 150.1(12) 2_656 . . . ? Eu1 O3 C8 C3 -26(2) 2_656 . . . ? C2 C3 C8 O3 -91.2(11) . . . . ? C4 C3 C8 O3 85.3(10) . . . . ? C2 C3 C8 O4 92.7(10) . . . . ? C4 C3 C8 O4 -90.8(9) . . . . ? Eu1 O6 C9 O5 -6.0(8) 1_655 . . . ? Eu1 O6 C9 C5 168.1(6) 1_655 . . . ? Eu1 O5 C9 O6 157.2(7) 2_666 . . . ? Eu1 O5 C9 O6 5.5(7) 1_655 . . . ? Eu1 O5 C9 C5 -17.0(14) 2_666 . . . ? Eu1 O5 C9 C5 -168.7(6) 1_655 . . . ? Eu1 O5 C9 Eu1 151.7(10) 2_666 . . 1_655 ? C4 C5 C9 O6 -89.2(9) . . . . ? C6 C5 C9 O6 90.2(10) . . . . ? C4 C5 C9 O5 85.1(9) . . . . ? C6 C5 C9 O5 -95.6(9) . . . . ? C4 C5 C9 Eu1 -19(3) . . . 1_655 ? C6 C5 C9 Eu1 160(3) . . . 1_655 ? loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA _geom_hbond_site_symmetry_A O11 H11B O8 0.87 1.97 2.717(7) 143.2 1_554 O12 H12A O6 0.85 1.89 2.733(8) 168.6 2_666 O11 H11A O7 0.85 1.98 2.778(7) 154.6 2_666 O10 H10B O12 0.85 2.15 2.820(8) 135.6 1_546 O10 H10A O11 0.85 1.86 2.701(8) 167.8 2_566 O9 H9B O11 0.85 1.90 2.673(8) 149.8 2_566 O9 H9A O1 0.99 1.77 2.720(8) 161.0 2_566 O4 H4 O12 0.84 1.76 2.604(7) 178.4 2_665 _diffrn_measured_fraction_theta_max 0.986 _diffrn_reflns_theta_full 27.84 _diffrn_measured_fraction_theta_full 0.986 _refine_diff_density_max 2.030 _refine_diff_density_min -2.497 _refine_diff_density_rms 0.283 # Attachment '- complex 3.cif' data_r91002f _database_code_depnum_ccdc_archive 'CCDC 768998' #TrackingRef '- complex 3.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C9 H10 N O12 Pr' _chemical_formula_weight 465.09 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 Triclinic _symmetry_space_group_name_H-M P-1 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 8.4864(17) _cell_length_b 8.9615(18) _cell_length_c 9.4369(19) _cell_angle_alpha 95.53(3) _cell_angle_beta 115.45(3) _cell_angle_gamma 95.45(3) _cell_volume 637.6(2) _cell_formula_units_Z 2 _cell_measurement_temperature 113(2) _cell_measurement_reflns_used 2208 _cell_measurement_theta_min 2.360 _cell_measurement_theta_max 27.872 _exptl_crystal_description ? _exptl_crystal_colour ? _exptl_crystal_size_max 0.18 _exptl_crystal_size_mid 0.16 _exptl_crystal_size_min 0.10 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 2.423 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 452 _exptl_absorpt_coefficient_mu 3.896 _exptl_absorpt_correction_type MULTI-SCAN _exptl_absorpt_correction_T_min 0.5406 _exptl_absorpt_correction_T_max 0.6967 _exptl_absorpt_process_details crystalclear _exptl_special_details ; ? ; _diffrn_ambient_temperature 113(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 'rigaku saturn CCD area detector' _diffrn_measurement_method '\w and \f scans' _diffrn_detector_area_resol_mean 7.31 _diffrn_standards_number 0 _diffrn_standards_interval_count 0 _diffrn_standards_interval_time 0 _diffrn_standards_decay_% 0 _diffrn_reflns_number 5531 _diffrn_reflns_av_R_equivalents 0.0354 _diffrn_reflns_av_sigmaI/netI 0.0696 _diffrn_reflns_limit_h_min -10 _diffrn_reflns_limit_h_max 10 _diffrn_reflns_limit_k_min -11 _diffrn_reflns_limit_k_max 11 _diffrn_reflns_limit_l_min -12 _diffrn_reflns_limit_l_max 11 _diffrn_reflns_theta_min 2.31 _diffrn_reflns_theta_max 27.81 _reflns_number_total 2910 _reflns_number_gt 2557 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'crystalclear(Rigaku/MSC Inc., 2005)' _computing_cell_refinement crystalclear _computing_data_reduction crystalclear _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^)+(0.0150P)^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 2910 _refine_ls_number_parameters 209 _refine_ls_number_restraints 6 _refine_ls_R_factor_all 0.0309 _refine_ls_R_factor_gt 0.0275 _refine_ls_wR_factor_ref 0.0609 _refine_ls_wR_factor_gt 0.0602 _refine_ls_goodness_of_fit_ref 1.023 _refine_ls_restrained_S_all 1.022 _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 Pr1 Pr 0.67971(2) 0.30371(2) 0.30549(2) 0.00600(7) Uani 1 1 d . . . O1 O 0.4128(3) 0.0971(3) 0.1586(3) 0.0088(6) Uani 1 1 d . . . O2 O 0.1631(3) -0.0686(3) 0.0312(3) 0.0111(6) Uani 1 1 d . . . H2A H 0.1759 -0.0513 -0.0495 0.017 Uiso 1 1 calc R . . O3 O 0.3715(4) -0.2517(3) 0.2372(3) 0.0206(7) Uani 1 1 d . . . O4 O 0.3611(3) -0.3333(3) 0.4508(3) 0.0108(6) Uani 1 1 d . . . O5 O 0.2212(3) -0.0764(3) 0.7880(3) 0.0092(6) Uani 1 1 d . . . O6 O 0.1854(4) 0.1681(3) 0.7943(3) 0.0168(7) Uani 1 1 d . . . O7 O -0.0199(3) 0.3246(3) 0.5165(3) 0.0095(6) Uani 1 1 d . . . O8 O 0.2643(3) 0.4243(3) 0.6084(3) 0.0122(6) Uani 1 1 d . . . O9 O 0.4041(3) 0.4150(3) 0.2403(3) 0.0158(6) Uani 1 1 d . . . H9A H 0.3959 0.4839 0.3046 0.024 Uiso 1 1 d R . . H9B H 0.3153 0.3965 0.1501 0.024 Uiso 1 1 d R . . O10 O 0.9217(3) 0.4252(3) 0.2283(3) 0.0142(6) Uani 1 1 d . . . H10A H 0.9001 0.4691 0.1476 0.021 Uiso 1 1 d R . . H10B H 0.9765 0.4895 0.3124 0.021 Uiso 1 1 d R . . O11 O 0.5518(4) 0.3297(4) 0.0130(3) 0.0258(8) Uani 1 1 d . . . H11A H 0.6020 0.3337 -0.0481 0.039 Uiso 1 1 d R . . H11B H 0.4542 0.2701 -0.0282 0.039 Uiso 1 1 d R . . N1 N 0.2750(4) -0.0748(4) 0.5343(3) 0.0064(6) Uani 1 1 d . . . C1 C 0.3461(5) -0.2366(4) 0.3574(4) 0.0090(8) Uani 1 1 d . . . C2 C 0.2900(5) -0.0899(4) 0.3977(4) 0.0053(7) Uani 1 1 d . . . C3 C 0.2569(5) 0.0259(4) 0.3042(4) 0.0069(8) Uani 1 1 d . . . C4 C 0.2055(4) 0.1553(4) 0.3519(4) 0.0078(8) Uani 1 1 d . . . H4 H 0.1828 0.2347 0.2892 0.009 Uiso 1 1 calc R . . C5 C 0.1866(4) 0.1698(4) 0.4926(4) 0.0059(8) Uani 1 1 d . . . C6 C 0.2232(5) 0.0495(4) 0.5798(4) 0.0057(7) Uani 1 1 d . . . C7 C 0.2085(5) 0.0501(4) 0.7338(4) 0.0080(8) Uani 1 1 d . . . C8 C 0.2863(5) 0.0183(4) 0.1569(4) 0.0073(8) Uani 1 1 d U . . C9 C 0.1386(5) 0.3163(4) 0.5448(4) 0.0065(8) Uani 1 1 d . . . O12 O 0.9149(3) 0.6516(3) 0.0281(3) 0.0158(6) Uani 1 1 d . . . H12A H 0.8773 0.7106 0.0789 0.024 Uiso 1 1 d R . . H12B H 1.0191 0.6873 0.0455 0.024 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 0.00804(14) 0.00338(12) 0.00740(12) 0.00163(8) 0.00386(10) 0.00173(9) O1 0.0083(14) 0.0080(14) 0.0110(13) 0.0000(10) 0.0059(12) -0.0015(11) O2 0.0111(15) 0.0173(17) 0.0039(13) -0.0003(11) 0.0034(12) -0.0008(11) O3 0.0345(18) 0.0220(19) 0.0175(15) 0.0087(13) 0.0193(14) 0.0163(14) O4 0.0123(14) 0.0103(16) 0.0140(14) 0.0059(11) 0.0080(12) 0.0067(11) O5 0.0170(15) 0.0061(14) 0.0081(13) 0.0043(10) 0.0077(12) 0.0040(11) O6 0.0351(18) 0.0093(16) 0.0142(14) 0.0054(11) 0.0161(14) 0.0112(13) O7 0.0100(15) 0.0076(15) 0.0114(13) 0.0024(11) 0.0049(12) 0.0020(11) O8 0.0112(15) 0.0026(15) 0.0249(16) -0.0002(11) 0.0104(13) 0.0017(11) O9 0.0118(15) 0.0102(16) 0.0194(15) -0.0036(12) 0.0020(13) 0.0038(12) O10 0.0180(16) 0.0112(16) 0.0130(14) 0.0007(11) 0.0074(12) -0.0018(12) O11 0.0168(17) 0.050(2) 0.0121(15) 0.0067(15) 0.0080(13) 0.0015(15) N1 0.0042(16) 0.0059(17) 0.0070(15) -0.0003(12) 0.0014(13) -0.0014(12) C1 0.008(2) 0.007(2) 0.0111(19) -0.0007(14) 0.0040(16) 0.0035(15) C2 0.0047(19) 0.0039(19) 0.0087(18) -0.0005(14) 0.0048(15) -0.0004(14) C3 0.0042(19) 0.011(2) 0.0059(17) 0.0028(14) 0.0023(15) 0.0003(15) C4 0.006(2) 0.008(2) 0.0087(18) 0.0026(14) 0.0027(16) -0.0021(15) C5 0.0032(19) 0.005(2) 0.0088(18) -0.0014(14) 0.0032(15) -0.0028(14) C6 0.0044(19) 0.0051(19) 0.0069(17) 0.0011(14) 0.0021(15) -0.0002(14) C7 0.007(2) 0.009(2) 0.0058(18) -0.0006(14) 0.0018(16) -0.0008(15) C8 0.011(2) 0.0042(19) 0.0083(18) 0.0021(14) 0.0047(16) 0.0060(15) C9 0.012(2) 0.005(2) 0.0055(17) 0.0040(14) 0.0051(16) 0.0045(15) O12 0.0153(16) 0.0175(17) 0.0180(15) -0.0015(12) 0.0108(13) 0.0055(12) _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 O8 2.428(3) 2_666 ? Pr1 O7 2.444(3) 1_655 ? Pr1 O4 2.463(3) 2_656 ? Pr1 O9 2.484(3) . ? Pr1 O5 2.500(3) 2_656 ? Pr1 O11 2.539(3) . ? Pr1 O1 2.548(3) . ? Pr1 N1 2.625(3) 2_656 ? Pr1 O10 2.636(3) . ? O1 C8 1.220(4) . ? O2 C8 1.307(4) . ? O2 H2A 0.8400 . ? O3 C1 1.239(4) . ? O4 C1 1.271(4) . ? O4 Pr1 2.463(3) 2_656 ? O5 C7 1.283(4) . ? O5 Pr1 2.500(3) 2_656 ? O6 C7 1.226(5) . ? O7 C9 1.265(4) . ? O7 Pr1 2.444(3) 1_455 ? O8 C9 1.256(4) . ? O8 Pr1 2.428(3) 2_666 ? O9 H9A 0.8519 . ? O9 H9B 0.8475 . ? O10 H10A 0.8487 . ? O10 H10B 0.8493 . ? O11 H11A 0.8528 . ? O11 H11B 0.8491 . ? N1 C6 1.336(5) . ? N1 C2 1.344(4) . ? N1 Pr1 2.625(3) 2_656 ? C1 C2 1.509(5) . ? C2 C3 1.397(5) . ? C3 C4 1.379(5) . ? C3 C8 1.511(5) . ? C4 C5 1.400(5) . ? C4 H4 0.9500 . ? C5 C6 1.396(5) . ? C5 C9 1.510(5) . ? C6 C7 1.511(5) . ? O12 H12A 0.8529 . ? O12 H12B 0.8503 . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag O8 Pr1 O7 81.19(10) 2_666 1_655 ? O8 Pr1 O4 75.38(9) 2_666 2_656 ? O7 Pr1 O4 76.80(9) 1_655 2_656 ? O8 Pr1 O9 67.32(9) 2_666 . ? O7 Pr1 O9 140.81(9) 1_655 . ? O4 Pr1 O9 73.21(9) 2_656 . ? O8 Pr1 O5 147.73(8) 2_666 2_656 ? O7 Pr1 O5 79.27(9) 1_655 2_656 ? O4 Pr1 O5 123.91(8) 2_656 2_656 ? O9 Pr1 O5 139.03(9) . 2_656 ? O8 Pr1 O11 93.53(10) 2_666 . ? O7 Pr1 O11 133.85(9) 1_655 . ? O4 Pr1 O11 146.18(9) 2_656 . ? O9 Pr1 O11 73.03(10) . . ? O5 Pr1 O11 82.01(10) 2_656 . ? O8 Pr1 O1 137.54(8) 2_666 . ? O7 Pr1 O1 137.02(9) 1_655 . ? O4 Pr1 O1 93.83(8) 2_656 . ? O9 Pr1 O1 70.24(9) . . ? O5 Pr1 O1 71.59(9) 2_656 . ? O11 Pr1 O1 72.75(9) . . ? O8 Pr1 N1 131.49(9) 2_666 2_656 ? O7 Pr1 N1 67.28(9) 1_655 2_656 ? O4 Pr1 N1 62.49(9) 2_656 2_656 ? O9 Pr1 N1 117.51(9) . 2_656 ? O5 Pr1 N1 61.53(9) 2_656 2_656 ? O11 Pr1 N1 134.92(10) . 2_656 ? O1 Pr1 N1 71.20(9) . 2_656 ? O8 Pr1 O10 71.50(9) 2_666 . ? O7 Pr1 O10 66.85(8) 1_655 . ? O4 Pr1 O10 133.58(9) 2_656 . ? O9 Pr1 O10 120.04(9) . . ? O5 Pr1 O10 77.28(8) 2_656 . ? O11 Pr1 O10 68.03(9) . . ? O1 Pr1 O10 132.47(8) . . ? N1 Pr1 O10 122.36(9) 2_656 . ? C8 O1 Pr1 149.1(2) . . ? C8 O2 H2A 109.5 . . ? C1 O4 Pr1 127.3(2) . 2_656 ? C7 O5 Pr1 126.8(2) . 2_656 ? C9 O7 Pr1 144.1(2) . 1_455 ? C9 O8 Pr1 140.5(2) . 2_666 ? Pr1 O9 H9A 121.9 . . ? Pr1 O9 H9B 123.9 . . ? H9A O9 H9B 113.8 . . ? Pr1 O10 H10A 124.7 . . ? Pr1 O10 H10B 96.3 . . ? H10A O10 H10B 109.7 . . ? Pr1 O11 H11A 129.9 . . ? Pr1 O11 H11B 103.8 . . ? H11A O11 H11B 113.3 . . ? C6 N1 C2 120.2(3) . . ? C6 N1 Pr1 120.8(2) . 2_656 ? C2 N1 Pr1 118.8(2) . 2_656 ? O3 C1 O4 126.6(4) . . ? O3 C1 C2 117.5(3) . . ? O4 C1 C2 116.0(3) . . ? N1 C2 C3 120.6(3) . . ? N1 C2 C1 115.3(3) . . ? C3 C2 C1 124.2(3) . . ? C4 C3 C2 119.4(3) . . ? C4 C3 C8 118.5(3) . . ? C2 C3 C8 122.0(3) . . ? C3 C4 C5 120.1(3) . . ? C3 C4 H4 120.0 . . ? C5 C4 H4 120.0 . . ? C6 C5 C4 117.1(4) . . ? C6 C5 C9 124.4(3) . . ? C4 C5 C9 118.4(3) . . ? N1 C6 C5 122.7(3) . . ? N1 C6 C7 114.6(3) . . ? C5 C6 C7 122.7(3) . . ? O6 C7 O5 126.4(3) . . ? O6 C7 C6 118.3(3) . . ? O5 C7 C6 115.3(3) . . ? O1 C8 O2 124.6(3) . . ? O1 C8 C3 119.9(3) . . ? O2 C8 C3 115.3(3) . . ? O8 C9 O7 125.3(4) . . ? O8 C9 C5 114.7(3) . . ? O7 C9 C5 119.9(3) . . ? H12A O12 H12B 110.3 . . ? 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 O8 Pr1 O1 C8 -70.2(5) 2_666 . . . ? O7 Pr1 O1 C8 77.0(5) 1_655 . . . ? O4 Pr1 O1 C8 2.3(5) 2_656 . . . ? O9 Pr1 O1 C8 -68.3(5) . . . . ? O5 Pr1 O1 C8 126.8(5) 2_656 . . . ? O11 Pr1 O1 C8 -146.0(5) . . . . ? N1 Pr1 O1 C8 61.5(5) 2_656 . . . ? O10 Pr1 O1 C8 178.6(4) . . . . ? Pr1 O4 C1 O3 178.0(3) 2_656 . . . ? Pr1 O4 C1 C2 -2.6(4) 2_656 . . . ? C6 N1 C2 C3 2.0(5) . . . . ? Pr1 N1 C2 C3 176.3(2) 2_656 . . . ? C6 N1 C2 C1 -178.8(3) . . . . ? Pr1 N1 C2 C1 -4.5(4) 2_656 . . . ? O3 C1 C2 N1 -176.0(3) . . . . ? O4 C1 C2 N1 4.6(5) . . . . ? O3 C1 C2 C3 3.2(5) . . . . ? O4 C1 C2 C3 -176.2(3) . . . . ? N1 C2 C3 C4 -1.1(5) . . . . ? C1 C2 C3 C4 179.7(3) . . . . ? N1 C2 C3 C8 175.1(3) . . . . ? C1 C2 C3 C8 -4.1(5) . . . . ? C2 C3 C4 C5 -0.1(5) . . . . ? C8 C3 C4 C5 -176.4(3) . . . . ? C3 C4 C5 C6 0.5(5) . . . . ? C3 C4 C5 C9 177.1(3) . . . . ? C2 N1 C6 C5 -1.6(5) . . . . ? Pr1 N1 C6 C5 -175.8(3) 2_656 . . . ? C2 N1 C6 C7 178.8(3) . . . . ? Pr1 N1 C6 C7 4.6(4) 2_656 . . . ? C4 C5 C6 N1 0.3(5) . . . . ? C9 C5 C6 N1 -176.1(3) . . . . ? C4 C5 C6 C7 179.9(3) . . . . ? C9 C5 C6 C7 3.5(5) . . . . ? Pr1 O5 C7 O6 -168.4(3) 2_656 . . . ? Pr1 O5 C7 C6 11.9(4) 2_656 . . . ? N1 C6 C7 O6 170.2(3) . . . . ? C5 C6 C7 O6 -9.5(5) . . . . ? N1 C6 C7 O5 -10.1(5) . . . . ? C5 C6 C7 O5 170.3(3) . . . . ? Pr1 O1 C8 O2 170.4(3) . . . . ? Pr1 O1 C8 C3 -4.9(7) . . . . ? C4 C3 C8 O1 70.2(5) . . . . ? C2 C3 C8 O1 -106.0(4) . . . . ? C4 C3 C8 O2 -105.5(4) . . . . ? C2 C3 C8 O2 78.2(4) . . . . ? Pr1 O8 C9 O7 -7.5(6) 2_666 . . . ? Pr1 O8 C9 C5 169.1(2) 2_666 . . . ? Pr1 O7 C9 O8 115.8(4) 1_455 . . . ? Pr1 O7 C9 C5 -60.7(5) 1_455 . . . ? C6 C5 C9 O8 98.5(4) . . . . ? C4 C5 C9 O8 -77.8(4) . . . . ? C6 C5 C9 O7 -84.6(4) . . . . ? C4 C5 C9 O7 99.0(4) . . . . ? _diffrn_measured_fraction_theta_max 0.964 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 0.969 _refine_diff_density_max 0.960 _refine_diff_density_min -1.280 _refine_diff_density_rms 0.175 # Attachment '- complex 1.cif' data_r91110g1 _database_code_depnum_ccdc_archive 'CCDC 768999' #TrackingRef '- complex 1.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C9 H10 La N O12' _chemical_formula_weight 463.09 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 8.4917(17) _cell_length_b 9.0243(18) _cell_length_c 9.0255(18) _cell_angle_alpha 78.37(3) _cell_angle_beta 65.06(3) _cell_angle_gamma 84.04(3) _cell_volume 614.1(2) _cell_formula_units_Z 2 _cell_measurement_temperature 113(2) _cell_measurement_reflns_used 2301 _cell_measurement_theta_min 2.2945 _cell_measurement_theta_max 27.801 _exptl_crystal_description ? _exptl_crystal_colour ? _exptl_crystal_size_max 0.10 _exptl_crystal_size_mid 0.08 _exptl_crystal_size_min 0.04 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 2.504 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 448 _exptl_absorpt_coefficient_mu 3.556 _exptl_absorpt_correction_type MULTI-SCAN _exptl_absorpt_correction_T_min 0.7175 _exptl_absorpt_correction_T_max 0.8708 _exptl_absorpt_process_details crystalclear _exptl_special_details ; ? ; _diffrn_ambient_temperature 113(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'rotating anode' _diffrn_radiation_monochromator multilayer _diffrn_measurement_device_type 'rigaku saturn CCD area detector' _diffrn_measurement_method '\w and \f scans' _diffrn_detector_area_resol_mean 7.31 _diffrn_standards_number 0 _diffrn_standards_interval_count 0 _diffrn_standards_interval_time 0 _diffrn_standards_decay_% 0 _diffrn_reflns_number 8109 _diffrn_reflns_av_R_equivalents 0.0296 _diffrn_reflns_av_sigmaI/netI 0.0351 _diffrn_reflns_limit_h_min -10 _diffrn_reflns_limit_h_max 11 _diffrn_reflns_limit_k_min -11 _diffrn_reflns_limit_k_max 11 _diffrn_reflns_limit_l_min -12 _diffrn_reflns_limit_l_max 12 _diffrn_reflns_theta_min 2.30 _diffrn_reflns_theta_max 29.95 _reflns_number_total 3027 _reflns_number_gt 2825 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'crystalclear(Rigaku/MSC Inc., 2005)' _computing_cell_refinement crystalclear _computing_data_reduction crystalclear _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^)+(0.0288P)^2^+0.1838P] 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 SHELXL _refine_ls_extinction_coef 0.0240(11) _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_number_reflns 3027 _refine_ls_number_parameters 230 _refine_ls_number_restraints 15 _refine_ls_R_factor_all 0.0268 _refine_ls_R_factor_gt 0.0239 _refine_ls_wR_factor_ref 0.0571 _refine_ls_wR_factor_gt 0.0558 _refine_ls_goodness_of_fit_ref 1.131 _refine_ls_restrained_S_all 1.130 _refine_ls_shift/su_max 0.002 _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 -0.37198(2) 0.304915(17) 0.694658(18) 0.00564(8) Uani 1 1 d . . . O1 O -0.2546(3) 0.0990(2) 0.8458(2) 0.0094(4) Uani 1 1 d . . . O2 O -0.1327(3) -0.0672(2) 0.9705(2) 0.0095(4) Uani 1 1 d U . . H2 H -0.222(5) -0.064(4) 1.044(5) 0.011 Uiso 1 1 d . . . O3 O -0.1433(3) -0.2420(3) 0.7638(3) 0.0194(5) Uani 1 1 d . . . O4 O 0.0810(3) -0.3309(2) 0.5559(3) 0.0104(4) Uani 1 1 d . . . O5 O 0.5664(3) -0.0738(2) 0.2113(2) 0.0075(4) Uani 1 1 d . . . O6 O 0.6092(3) 0.1680(3) 0.2084(3) 0.0180(5) Uani 1 1 d . . . O7 O 0.5354(3) 0.3235(2) 0.4832(2) 0.0085(4) Uani 1 1 d . . . O8 O 0.3423(3) 0.4212(2) 0.3958(3) 0.0126(5) Uani 1 1 d . . . O9 O -0.1537(3) 0.4185(3) 0.7548(3) 0.0137(5) Uani 1 1 d D . . H9A H -0.136(4) 0.391(4) 0.842(3) 0.016 Uiso 1 1 d D . . H9B H -0.096(4) 0.494(3) 0.687(3) 0.016 Uiso 1 1 d D . . O10 O -0.6959(3) 0.4287(2) 0.7714(3) 0.0133(4) Uani 1 1 d D . . H10A H -0.664(4) 0.495(3) 0.683(2) 0.016 Uiso 1 1 d D . . H10B H -0.763(4) 0.462(3) 0.859(2) 0.016 Uiso 1 1 d D . . O11 O -0.5383(3) 0.3433(3) 0.9898(3) 0.0205(5) Uani 1 1 d . . . H11B H -0.4699 0.3072 1.0356 0.025 Uiso 1 1 d R . . H11A H -0.6385 0.3174 1.0644 0.025 Uiso 1 1 d R . . N1 N 0.2563(3) -0.0738(3) 0.4673(3) 0.0055(5) Uani 1 1 d . . . C1 C -0.1295(4) 0.0190(3) 0.8461(3) 0.0069(5) Uani 1 1 d . . . C2 C 0.0462(4) 0.0257(3) 0.6989(3) 0.0064(5) Uani 1 1 d . . . C3 C 0.1477(4) 0.1539(3) 0.6501(3) 0.0074(5) Uani 1 1 d . . . H3 H 0.1089 0.2330 0.7135 0.009 Uiso 1 1 calc R . . C4 C 0.3055(4) 0.1676(3) 0.5092(3) 0.0067(5) Uani 1 1 d . . . C5 C 0.3552(4) 0.0494(3) 0.4213(3) 0.0067(5) Uani 1 1 d . . . C6 C 0.1053(4) -0.0876(3) 0.6035(3) 0.0063(5) Uani 1 1 d . . . C7 C 0.0046(4) -0.2316(3) 0.6456(3) 0.0089(6) Uani 1 1 d . . . C8 C 0.5234(4) 0.0507(3) 0.2676(3) 0.0078(5) Uani 1 1 d . . . C9 C 0.4057(4) 0.3142(3) 0.4565(3) 0.0058(5) Uani 1 1 d . . . O12 O 0.8879(3) 0.3466(3) 0.0263(3) 0.0153(5) Uani 1 1 d D . . H12A H 0.815(3) 0.277(3) 0.077(4) 0.018 Uiso 1 1 d D . . H12B H 0.9894(19) 0.330(4) 0.019(5) 0.018 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 0.00795(11) 0.00477(10) 0.00461(9) -0.00046(6) -0.00318(7) 0.00001(6) O1 0.0097(11) 0.0110(10) 0.0067(9) 0.0004(8) -0.0040(8) 0.0020(8) O2 0.0082(10) 0.0153(11) 0.0011(9) 0.0018(8) 0.0000(8) 0.0015(9) O3 0.0178(13) 0.0188(12) 0.0139(11) -0.0073(9) 0.0047(10) -0.0097(10) O4 0.0143(11) 0.0087(10) 0.0086(10) -0.0028(8) -0.0042(9) -0.0023(8) O5 0.0095(10) 0.0070(10) 0.0048(9) -0.0026(7) -0.0011(8) 0.0003(8) O6 0.0212(13) 0.0118(11) 0.0119(11) -0.0031(9) 0.0041(10) -0.0079(10) O7 0.0115(11) 0.0090(10) 0.0066(9) 0.0009(8) -0.0061(9) -0.0008(8) O8 0.0169(12) 0.0072(10) 0.0187(11) 0.0019(8) -0.0139(10) -0.0001(9) O9 0.0230(13) 0.0110(11) 0.0114(10) 0.0039(8) -0.0125(10) -0.0066(9) O10 0.0150(12) 0.0128(11) 0.0097(10) -0.0002(8) -0.0040(9) 0.0012(9) O11 0.0129(12) 0.0401(16) 0.0081(10) -0.0060(10) -0.0025(9) -0.0027(11) N1 0.0073(12) 0.0061(11) 0.0031(10) 0.0020(8) -0.0033(10) -0.0001(9) C1 0.0096(14) 0.0066(13) 0.0056(12) -0.0002(10) -0.0037(11) -0.0038(11) C2 0.0082(14) 0.0089(13) 0.0027(12) -0.0008(10) -0.0030(11) 0.0009(11) C3 0.0077(14) 0.0093(13) 0.0063(12) -0.0022(10) -0.0043(11) 0.0029(11) C4 0.0083(14) 0.0074(13) 0.0060(12) -0.0003(10) -0.0053(11) 0.0020(11) C5 0.0072(14) 0.0073(13) 0.0058(12) 0.0002(10) -0.0039(11) 0.0010(11) C6 0.0069(14) 0.0058(13) 0.0064(12) 0.0001(10) -0.0036(11) 0.0010(10) C7 0.0104(15) 0.0104(14) 0.0054(12) -0.0001(10) -0.0032(12) -0.0011(11) C8 0.0102(14) 0.0078(13) 0.0050(12) 0.0007(10) -0.0033(11) -0.0006(11) C9 0.0086(14) 0.0045(12) 0.0032(11) -0.0015(9) -0.0012(11) 0.0001(10) O12 0.0150(12) 0.0186(12) 0.0123(11) 0.0026(9) -0.0068(10) -0.0054(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 2.324(2) 1_455 ? La1 O8 2.446(2) 2_566 ? La1 O1 2.459(2) . ? La1 O9 2.500(2) . ? La1 O11 2.511(2) . ? La1 O4 2.544(2) 2_556 ? La1 O5 2.572(2) 2_556 ? La1 N1 2.654(3) 2_556 ? La1 O10 2.713(2) . ? O1 C1 1.222(4) . ? O2 C1 1.222(3) . ? O2 H2 0.77(4) . ? O3 C7 1.256(4) . ? O4 C7 1.268(4) . ? O4 La1 2.544(2) 2_556 ? O5 C8 1.282(4) . ? O5 La1 2.572(2) 2_556 ? O6 C8 1.241(4) . ? O7 C9 1.237(3) . ? O7 La1 2.324(2) 1_655 ? O8 C9 1.204(3) . ? O8 La1 2.446(2) 2_566 ? O9 H9A 0.847(10) . ? O9 H9B 0.851(10) . ? O10 H10A 0.852(10) . ? O10 H10B 0.850(10) . ? O11 H11B 0.8500 . ? O11 H11A 0.8527 . ? N1 C6 1.346(4) . ? N1 C5 1.352(4) . ? N1 La1 2.654(3) 2_556 ? C1 C2 1.519(4) . ? C2 C6 1.387(4) . ? C2 C3 1.399(4) . ? C3 C4 1.401(4) . ? C3 H3 0.9500 . ? C4 C5 1.383(4) . ? C4 C9 1.529(4) . ? C5 C8 1.513(4) . ? C6 C7 1.524(4) . ? O12 H12A 0.846(10) . ? O12 H12B 0.836(10) . ? 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 O8 83.26(7) 1_455 2_566 ? O7 La1 O1 134.76(7) 1_455 . ? O8 La1 O1 137.89(7) 2_566 . ? O7 La1 O9 139.57(7) 1_455 . ? O8 La1 O9 65.03(7) 2_566 . ? O1 La1 O9 72.93(7) . . ? O7 La1 O11 130.09(8) 1_455 . ? O8 La1 O11 89.90(9) 2_566 . ? O1 La1 O11 77.89(8) . . ? O9 La1 O11 76.67(8) . . ? O7 La1 O4 79.94(7) 1_455 2_556 ? O8 La1 O4 76.68(8) 2_566 2_556 ? O1 La1 O4 91.18(7) . 2_556 ? O9 La1 O4 69.22(7) . 2_556 ? O11 La1 O4 145.88(7) . 2_556 ? O7 La1 O5 76.96(7) 1_455 2_556 ? O8 La1 O5 147.70(7) 2_566 2_556 ? O1 La1 O5 71.51(7) . 2_556 ? O9 La1 O5 142.22(7) . 2_556 ? O11 La1 O5 83.81(8) . 2_556 ? O4 La1 O5 123.53(7) 2_556 2_556 ? O7 La1 N1 68.08(7) 1_455 2_556 ? O8 La1 N1 132.61(7) 2_566 2_556 ? O1 La1 N1 68.61(7) . 2_556 ? O9 La1 N1 115.49(8) . 2_556 ? O11 La1 N1 137.45(8) . 2_556 ? O4 La1 N1 62.13(7) 2_556 2_556 ? O5 La1 N1 61.49(7) 2_556 2_556 ? O7 La1 O10 66.96(7) 1_455 . ? O8 La1 O10 72.40(8) 2_566 . ? O1 La1 O10 132.05(7) . . ? O9 La1 O10 120.86(7) . . ? O11 La1 O10 63.88(8) . . ? O4 La1 O10 136.60(7) 2_556 . ? O5 La1 O10 76.42(7) 2_556 . ? N1 La1 O10 123.48(7) 2_556 . ? C1 O1 La1 147.6(2) . . ? C1 O2 H2 111(3) . . ? C7 O4 La1 126.49(19) . 2_556 ? C8 O5 La1 125.80(19) . 2_556 ? C9 O7 La1 142.82(19) . 1_655 ? C9 O8 La1 140.8(2) . 2_566 ? La1 O9 H9A 124(2) . . ? La1 O9 H9B 119(2) . . ? H9A O9 H9B 116.2(18) . . ? La1 O10 H10A 93(2) . . ? La1 O10 H10B 128(2) . . ? H10A O10 H10B 115.1(17) . . ? La1 O11 H11B 103.5 . . ? La1 O11 H11A 133.8 . . ? H11B O11 H11A 103.7 . . ? C6 N1 C5 121.0(2) . . ? C6 N1 La1 118.63(18) . 2_556 ? C5 N1 La1 120.08(18) . 2_556 ? O1 C1 O2 122.0(3) . . ? O1 C1 C2 123.8(3) . . ? O2 C1 C2 114.0(3) . . ? C6 C2 C3 118.2(3) . . ? C6 C2 C1 122.0(3) . . ? C3 C2 C1 119.6(2) . . ? C2 C3 C4 121.1(3) . . ? C2 C3 H3 119.4 . . ? C4 C3 H3 119.4 . . ? C5 C4 C3 116.9(3) . . ? C5 C4 C9 124.2(3) . . ? C3 C4 C9 118.7(3) . . ? N1 C5 C4 122.0(3) . . ? N1 C5 C8 116.1(2) . . ? C4 C5 C8 121.9(3) . . ? N1 C6 C2 120.6(3) . . ? N1 C6 C7 116.9(2) . . ? C2 C6 C7 122.4(3) . . ? O3 C7 O4 126.2(3) . . ? O3 C7 C6 118.3(3) . . ? O4 C7 C6 115.5(3) . . ? O6 C8 O5 125.4(3) . . ? O6 C8 C5 118.9(3) . . ? O5 C8 C5 115.7(3) . . ? O8 C9 O7 122.9(3) . . ? O8 C9 C4 114.5(2) . . ? O7 C9 C4 122.4(2) . . ? H12A O12 H12B 118.7(19) . . ? 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 O1 C1 78.0(4) 1_455 . . . ? O8 La1 O1 C1 -70.3(4) 2_566 . . . ? O9 La1 O1 C1 -66.8(4) . . . . ? O11 La1 O1 C1 -146.4(4) . . . . ? O4 La1 O1 C1 1.0(4) 2_556 . . . ? O5 La1 O1 C1 126.1(4) 2_556 . . . ? N1 La1 O1 C1 60.3(4) 2_556 . . . ? O10 La1 O1 C1 176.7(3) . . . . ? La1 O1 C1 O2 172.2(2) . . . . ? La1 O1 C1 C2 -3.0(5) . . . . ? O1 C1 C2 C6 -107.5(3) . . . . ? O2 C1 C2 C6 77.0(3) . . . . ? O1 C1 C2 C3 68.2(4) . . . . ? O2 C1 C2 C3 -107.3(3) . . . . ? C6 C2 C3 C4 -0.4(4) . . . . ? C1 C2 C3 C4 -176.2(2) . . . . ? C2 C3 C4 C5 0.3(4) . . . . ? C2 C3 C4 C9 176.6(2) . . . . ? C6 N1 C5 C4 -1.0(4) . . . . ? La1 N1 C5 C4 -175.34(19) 2_556 . . . ? C6 N1 C5 C8 179.0(2) . . . . ? La1 N1 C5 C8 4.7(3) 2_556 . . . ? C3 C4 C5 N1 0.5(4) . . . . ? C9 C4 C5 N1 -175.6(2) . . . . ? C3 C4 C5 C8 -179.6(2) . . . . ? C9 C4 C5 C8 4.3(4) . . . . ? C5 N1 C6 C2 0.9(4) . . . . ? La1 N1 C6 C2 175.25(19) 2_556 . . . ? C5 N1 C6 C7 -179.3(2) . . . . ? La1 N1 C6 C7 -5.0(3) 2_556 . . . ? C3 C2 C6 N1 -0.1(4) . . . . ? C1 C2 C6 N1 175.5(2) . . . . ? C3 C2 C6 C7 -179.9(2) . . . . ? C1 C2 C6 C7 -4.2(4) . . . . ? La1 O4 C7 O3 175.9(2) 2_556 . . . ? La1 O4 C7 C6 -4.3(3) 2_556 . . . ? N1 C6 C7 O3 -174.2(3) . . . . ? C2 C6 C7 O3 5.6(4) . . . . ? N1 C6 C7 O4 6.0(4) . . . . ? C2 C6 C7 O4 -174.2(3) . . . . ? La1 O5 C8 O6 -170.7(2) 2_556 . . . ? La1 O5 C8 C5 10.6(3) 2_556 . . . ? N1 C5 C8 O6 171.6(3) . . . . ? C4 C5 C8 O6 -8.3(4) . . . . ? N1 C5 C8 O5 -9.6(4) . . . . ? C4 C5 C8 O5 170.5(2) . . . . ? La1 O8 C9 O7 -5.2(5) 2_566 . . . ? La1 O8 C9 C4 170.8(2) 2_566 . . . ? La1 O7 C9 O8 113.1(3) 1_655 . . . ? La1 O7 C9 C4 -62.6(4) 1_655 . . . ? C5 C4 C9 O8 103.2(3) . . . . ? C3 C4 C9 O8 -72.9(3) . . . . ? C5 C4 C9 O7 -80.8(4) . . . . ? C3 C4 C9 O7 103.1(3) . . . . ? _diffrn_measured_fraction_theta_max 0.850 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 0.999 _refine_diff_density_max 1.363 _refine_diff_density_min -0.864 _refine_diff_density_rms 0.151