Supplementary Material (ESI) for Dalton Transactions This journal is (c) The Royal Society of Chemistry 2007 data_global _journal_name_full 'Dalton Trans.' _journal_coden_Cambridge 0222 _publ_contact_author_name 'Hiroshi Tsukube' _publ_contact_author_address ; Department of Chemistry Graduate School of Science Osaka City University 3-3-138 Sugimoto, Sumiyoshi-ku, Osaka 558-8585, Japan ; _publ_contact_author_email TSUKUBE@SCI.OSAKA-CU.AC.J _publ_section_title ; Cl- Anion-responsive luminescent Eu3+ complex with chiral tripode: ligand substitution effects on ternary complex stoichiometry and anion sensing selectivity ; loop_ _publ_author_name 'Yumiko Kataoka' 'Dharam Paul' 'Hiroyuki Miyake' 'Satoshi Shinoda' 'Hiroshi Tsukube' # Attachment 'La_1a.cif' data_[La(1a)(NO3)3] _database_code_depnum_ccdc_archive 'CCDC 265041' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_formula_moiety 'C26 H28 La N7 O10' _chemical_formula_sum 'C26 H28 La N7 O10' _chemical_formula_weight 737.46 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' N N 0.0061 0.0033 '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' 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 monoclinic _symmetry_space_group_name_H-M 'P 21/n' _symmetry_space_group_name_Hall '-P 2yn' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, y+1/2, -z+1/2' '-x, -y, -z' 'x-1/2, -y-1/2, z-1/2' _cell_length_a 10.1150(8) _cell_length_b 16.3586(9) _cell_length_c 18.1262(14) _cell_angle_alpha 90.00 _cell_angle_beta 108.113(3) _cell_angle_gamma 90.00 _cell_volume 2850.7(4) _cell_formula_units_Z 4 _cell_measurement_temperature 123(2) _cell_measurement_reflns_used 7457 _cell_measurement_theta_min 3.2438 _cell_measurement_theta_max 27.4835 _exptl_crystal_description Platelet _exptl_crystal_colour Colorless _exptl_crystal_size_max 0.20 _exptl_crystal_size_mid 0.12 _exptl_crystal_size_min 0.07 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.718 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1480 _exptl_absorpt_coefficient_mu 1.569 _exptl_absorpt_correction_type Multi-scan _exptl_absorpt_correction_T_min 0.7444 _exptl_absorpt_correction_T_max 0.8981 _exptl_absorpt_process_details '(Jacobson, 1998)' _exptl_special_details ; ? ; _diffrn_ambient_temperature 123(2) _diffrn_radiation_wavelength 0.71070 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'Rotating Anode' _diffrn_radiation_monochromator 'Graphite Monochromator' _diffrn_measurement_method \w _diffrn_radiation_detector CCD _diffrn_measurement_device ; Mercury CCD (2x2 bin mode) ; _diffrn_reflns_number 21953 _diffrn_reflns_av_R_equivalents 0.0292 _diffrn_reflns_av_sigmaI/netI 0.0280 _diffrn_reflns_limit_h_min -12 _diffrn_reflns_limit_h_max 13 _diffrn_reflns_limit_k_min -13 _diffrn_reflns_limit_k_max 21 _diffrn_reflns_limit_l_min -18 _diffrn_reflns_limit_l_max 23 _diffrn_reflns_theta_min 3.25 _diffrn_reflns_theta_max 27.48 _reflns_number_total 6427 _reflns_number_gt 5992 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'CrystalClear (Rigaku Corp., 2000)' _computing_cell_refinement 'CrystalClear (Rigaku Corp., 2000)' _computing_data_reduction 'CrystalClear (Rigaku Corp., 2000)' _computing_structure_solution 'DIRDIF-99 (Beurskens, 1999)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _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^)+(0.0086P)^2^+5.0573P] 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 6427 _refine_ls_number_parameters 399 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0435 _refine_ls_R_factor_gt 0.0368 _refine_ls_wR_factor_ref 0.0622 _refine_ls_wR_factor_gt 0.0605 _refine_ls_goodness_of_fit_ref 1.256 _refine_ls_restrained_S_all 1.256 _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 C1 C 0.2032(3) -0.05705(16) 0.15249(17) 0.0170(6) Uani 1 1 d . . . N1 N 0.1895(3) 0.02360(13) 0.14770(14) 0.0152(5) Uani 1 1 d . . . C2 C 0.1726(3) 0.05969(17) 0.07671(16) 0.0150(6) Uani 1 1 d . . . C3 C 0.1494(3) 0.14486(17) 0.06791(18) 0.0184(6) Uani 1 1 d . . . H1 H 0.1453 0.1766 0.1110 0.022 Uiso 1 1 calc R . . C4 C 0.1329(3) 0.18178(18) -0.00155(18) 0.0205(6) Uani 1 1 d . . . H2 H 0.1188 0.2392 -0.0062 0.025 Uiso 1 1 calc R . . C5 C 0.1366(3) 0.1359(2) -0.06679(19) 0.0241(7) Uani 1 1 d . . . H3 H 0.1265 0.1625 -0.1148 0.029 Uiso 1 1 calc R . . C6 C 0.1546(3) 0.05348(19) -0.06071(18) 0.0215(6) Uani 1 1 d . . . H4 H 0.1545 0.0226 -0.1051 0.026 Uiso 1 1 calc R . . C7 C 0.1734(3) 0.01321(17) 0.01082(17) 0.0171(6) Uani 1 1 d . . . C8 C 0.1909(3) -0.07239(17) 0.01951(18) 0.0190(6) Uani 1 1 d . . . H5 H 0.1930 -0.1053 -0.0233 0.023 Uiso 1 1 calc R . . C9 C 0.2048(3) -0.10700(18) 0.08932(18) 0.0199(6) Uani 1 1 d . . . H6 H 0.2156 -0.1645 0.0958 0.024 Uiso 1 1 calc R . . C10 C 0.2056(3) -0.09635(16) 0.22801(17) 0.0176(6) Uani 1 1 d . . . H7 H 0.1109 -0.0941 0.2328 0.021 Uiso 1 1 calc R . . H8 H 0.2311 -0.1546 0.2268 0.021 Uiso 1 1 calc R . . C11 C 0.1422(3) -0.07142(17) 0.37608(17) 0.0184(6) Uani 1 1 d . . . N2 N 0.0992(3) 0.00556(14) 0.36329(14) 0.0168(5) Uani 1 1 d . . . C12 C -0.0199(3) 0.02697(17) 0.38020(17) 0.0180(6) Uani 1 1 d . . . C13 C -0.0659(3) 0.10887(18) 0.37180(17) 0.0206(6) Uani 1 1 d . . . H9 H -0.0149 0.1490 0.3541 0.025 Uiso 1 1 calc R . . C14 C -0.1836(3) 0.13091(19) 0.38895(19) 0.0245(7) Uani 1 1 d . . . H10 H -0.2141 0.1861 0.3820 0.029 Uiso 1 1 calc R . . C15 C -0.2603(3) 0.0735(2) 0.41659(19) 0.0254(7) Uani 1 1 d . . . H11 H -0.3419 0.0898 0.4281 0.030 Uiso 1 1 calc R . . C16 C -0.2167(3) -0.0056(2) 0.42669(18) 0.0253(7) Uani 1 1 d . . . H12 H -0.2675 -0.0442 0.4462 0.030 Uiso 1 1 calc R . . C17 C -0.0969(3) -0.03133(18) 0.40857(17) 0.0200(6) Uani 1 1 d . . . C18 C -0.0500(4) -0.11276(19) 0.41726(18) 0.0251(7) Uani 1 1 d . . . H13 H -0.1010 -0.1535 0.4341 0.030 Uiso 1 1 calc R . . C19 C 0.0682(4) -0.13281(18) 0.40150(18) 0.0234(7) Uani 1 1 d . . . H14 H 0.1010 -0.1876 0.4075 0.028 Uiso 1 1 calc R . . C20 C 0.2806(3) -0.09345(16) 0.36729(17) 0.0193(6) Uani 1 1 d . . . H15 H 0.3552 -0.0746 0.4138 0.023 Uiso 1 1 calc R . . H16 H 0.2873 -0.1537 0.3647 0.023 Uiso 1 1 calc R . . C21 C 0.4488(3) -0.07557(17) 0.29969(19) 0.0198(6) Uani 1 1 d . . . H17 H 0.4511 -0.1279 0.2726 0.024 Uiso 1 1 calc R . . H18 H 0.5081 -0.0815 0.3543 0.024 Uiso 1 1 calc R . . C22 C 0.5053(3) -0.00784(16) 0.26125(17) 0.0168(6) Uani 1 1 d . . . O1 O 0.4594(2) 0.06275(11) 0.26408(12) 0.0186(4) Uani 1 1 d . . . N4 N 0.6038(3) -0.02165(14) 0.22913(15) 0.0197(5) Uani 1 1 d . . . C23 C 0.6653(3) -0.10307(19) 0.2271(2) 0.0295(7) Uani 1 1 d . . . H19 H 0.6620 -0.1347 0.2731 0.035 Uiso 1 1 calc R . . H20 H 0.7643 -0.0965 0.2303 0.035 Uiso 1 1 calc R . . C24 C 0.5911(4) -0.1504(2) 0.1546(3) 0.0412(10) Uani 1 1 d . . . H21 H 0.4940 -0.1592 0.1522 0.062 Uiso 1 1 calc R . . H22 H 0.6369 -0.2033 0.1555 0.062 Uiso 1 1 calc R . . H23 H 0.5941 -0.1194 0.1089 0.062 Uiso 1 1 calc R . . C25 C 0.6547(3) 0.04854(18) 0.19483(19) 0.0235(7) Uani 1 1 d . . . H24 H 0.7490 0.0360 0.1925 0.028 Uiso 1 1 calc R . . H25 H 0.6621 0.0967 0.2290 0.028 Uiso 1 1 calc R . . C26 C 0.5617(4) 0.0700(2) 0.1140(2) 0.0344(8) Uani 1 1 d . . . H26 H 0.5529 0.0225 0.0799 0.052 Uiso 1 1 calc R . . H27 H 0.6025 0.1157 0.0937 0.052 Uiso 1 1 calc R . . H28 H 0.4695 0.0857 0.1163 0.052 Uiso 1 1 calc R . . N3 N 0.3039(3) -0.05747(13) 0.29740(14) 0.0157(5) Uani 1 1 d . . . O2 O 0.3972(2) 0.08442(12) 0.43157(13) 0.0221(5) Uani 1 1 d . . . O3 O 0.2445(2) 0.18188(12) 0.41232(12) 0.0211(4) Uani 1 1 d . . . N5 N 0.3485(3) 0.14550(15) 0.45861(15) 0.0205(6) Uani 1 1 d . . . O4 O 0.3997(3) 0.16776(14) 0.52574(13) 0.0335(6) Uani 1 1 d . . . O5 O -0.0167(2) 0.10581(13) 0.20412(13) 0.0240(5) Uani 1 1 d . . . O6 O 0.0688(2) 0.22422(12) 0.24550(14) 0.0258(5) Uani 1 1 d . . . N6 N -0.0358(3) 0.18207(16) 0.20591(15) 0.0221(6) Uani 1 1 d . . . O7 O -0.1473(3) 0.21389(15) 0.17299(16) 0.0382(6) Uani 1 1 d . . . O8 O 0.4465(2) 0.21266(12) 0.33474(12) 0.0214(5) Uani 1 1 d . . . O9 O 0.3476(2) 0.21339(11) 0.21073(12) 0.0201(5) Uani 1 1 d . . . N7 N 0.4530(3) 0.23144(13) 0.26793(14) 0.0157(5) Uani 1 1 d . . . O10 O 0.5553(2) 0.26530(13) 0.25936(13) 0.0231(5) Uani 1 1 d . . . La1 La 0.246733(17) 0.105015(9) 0.288284(10) 0.01301(5) Uani 1 1 d . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 C1 0.0166(15) 0.0170(13) 0.0177(15) -0.0004(11) 0.0059(12) -0.0029(11) N1 0.0158(13) 0.0150(10) 0.0139(12) -0.0018(9) 0.0037(10) -0.0019(9) C2 0.0115(14) 0.0212(13) 0.0122(14) -0.0003(11) 0.0034(11) -0.0016(11) C3 0.0163(15) 0.0183(13) 0.0192(16) -0.0027(11) 0.0037(12) -0.0040(11) C4 0.0177(15) 0.0212(13) 0.0207(16) 0.0034(12) 0.0031(13) 0.0013(12) C5 0.0200(17) 0.0357(16) 0.0161(16) 0.0068(13) 0.0050(13) 0.0022(13) C6 0.0169(16) 0.0324(16) 0.0150(15) -0.0026(12) 0.0046(13) 0.0025(13) C7 0.0121(14) 0.0222(14) 0.0168(15) -0.0034(11) 0.0044(12) -0.0011(11) C8 0.0161(15) 0.0219(13) 0.0203(16) -0.0081(12) 0.0075(13) -0.0023(12) C9 0.0199(15) 0.0165(12) 0.0242(16) -0.0043(12) 0.0082(13) -0.0030(12) C10 0.0188(15) 0.0151(12) 0.0193(15) -0.0023(11) 0.0066(12) -0.0059(11) C11 0.0232(16) 0.0184(13) 0.0130(14) -0.0003(11) 0.0045(12) -0.0034(12) N2 0.0187(13) 0.0172(11) 0.0151(12) 0.0010(9) 0.0060(10) -0.0031(10) C12 0.0185(16) 0.0222(13) 0.0140(14) -0.0005(11) 0.0061(12) -0.0044(12) C13 0.0203(15) 0.0238(14) 0.0198(15) 0.0050(12) 0.0092(12) -0.0022(13) C14 0.0231(17) 0.0285(15) 0.0235(17) 0.0014(13) 0.0096(14) -0.0010(13) C15 0.0160(16) 0.0409(17) 0.0210(17) 0.0006(14) 0.0083(13) -0.0041(14) C16 0.0230(18) 0.0358(17) 0.0174(16) -0.0005(13) 0.0066(14) -0.0125(14) C17 0.0208(16) 0.0267(15) 0.0128(14) 0.0011(12) 0.0055(12) -0.0081(12) C18 0.0315(18) 0.0262(15) 0.0185(16) 0.0026(13) 0.0091(14) -0.0129(14) C19 0.0298(19) 0.0188(13) 0.0194(16) 0.0024(12) 0.0043(14) -0.0062(13) C20 0.0260(17) 0.0156(13) 0.0173(15) 0.0055(11) 0.0083(13) 0.0001(12) C21 0.0215(16) 0.0153(12) 0.0242(17) 0.0026(11) 0.0093(13) 0.0014(11) C22 0.0161(15) 0.0150(12) 0.0178(15) -0.0025(11) 0.0029(12) -0.0018(11) O1 0.0178(11) 0.0149(9) 0.0249(12) -0.0007(8) 0.0093(9) -0.0001(8) N4 0.0170(13) 0.0182(11) 0.0252(14) -0.0050(10) 0.0084(11) 0.0009(10) C23 0.0229(17) 0.0234(14) 0.047(2) -0.0042(15) 0.0184(16) 0.0047(14) C24 0.040(2) 0.0305(18) 0.063(3) -0.0215(18) 0.031(2) -0.0061(16) C25 0.0205(17) 0.0257(15) 0.0281(18) -0.0034(13) 0.0129(14) -0.0049(13) C26 0.030(2) 0.0434(19) 0.031(2) 0.0068(16) 0.0113(17) -0.0048(16) N3 0.0168(13) 0.0128(10) 0.0174(13) 0.0004(9) 0.0051(10) -0.0012(9) O2 0.0243(12) 0.0189(10) 0.0226(12) 0.0035(8) 0.0066(10) 0.0016(8) O3 0.0206(11) 0.0219(10) 0.0215(11) -0.0010(9) 0.0078(9) 0.0004(9) N5 0.0252(15) 0.0200(12) 0.0175(14) 0.0018(10) 0.0083(11) -0.0072(11) O4 0.0464(16) 0.0351(13) 0.0150(12) -0.0049(10) 0.0037(11) -0.0104(11) O5 0.0191(11) 0.0234(10) 0.0292(12) -0.0065(10) 0.0071(9) -0.0005(9) O6 0.0212(12) 0.0174(10) 0.0359(14) 0.0028(9) 0.0047(11) -0.0008(9) N6 0.0199(14) 0.0266(13) 0.0214(14) 0.0039(11) 0.0088(11) 0.0003(11) O7 0.0228(14) 0.0394(14) 0.0469(17) 0.0093(12) 0.0026(12) 0.0097(11) O8 0.0315(13) 0.0200(10) 0.0153(11) -0.0031(8) 0.0113(10) -0.0074(9) O9 0.0205(12) 0.0174(9) 0.0197(11) 0.0023(8) 0.0025(9) -0.0018(8) N7 0.0183(13) 0.0114(10) 0.0181(13) -0.0016(9) 0.0066(11) -0.0004(9) O10 0.0213(12) 0.0273(11) 0.0238(12) -0.0002(9) 0.0112(10) -0.0090(9) La1 0.01521(8) 0.01063(7) 0.01406(8) -0.00038(6) 0.00582(6) -0.00115(6) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag C1 N1 1.326(3) . ? C1 C9 1.411(4) . ? C1 C10 1.506(4) . ? N1 C2 1.377(4) . ? N1 La1 2.772(2) . ? C2 C3 1.414(4) . ? C2 C7 1.418(4) . ? C3 C4 1.359(4) . ? C3 H1 0.9500 . ? C4 C5 1.411(4) . ? C4 H2 0.9500 . ? C5 C6 1.360(4) . ? C5 H3 0.9500 . ? C6 C7 1.413(4) . ? C6 H4 0.9500 . ? C7 C8 1.414(4) . ? C8 C9 1.353(4) . ? C8 H5 0.9500 . ? C9 H6 0.9500 . ? C10 N3 1.482(4) . ? C10 H7 0.9900 . ? C10 H8 0.9900 . ? C11 N2 1.329(4) . ? C11 C19 1.413(4) . ? C11 C20 1.501(4) . ? N2 C12 1.378(4) . ? N2 La1 2.825(2) . ? C12 C13 1.411(4) . ? C12 C17 1.425(4) . ? C13 C14 1.369(4) . ? C13 H9 0.9500 . ? C14 C15 1.406(4) . ? C14 H10 0.9500 . ? C15 C16 1.361(5) . ? C15 H11 0.9500 . ? C16 C17 1.414(5) . ? C16 H12 0.9500 . ? C17 C18 1.406(4) . ? C18 C19 1.353(5) . ? C18 H13 0.9500 . ? C19 H14 0.9500 . ? C20 N3 1.481(4) . ? C20 H15 0.9900 . ? C20 H16 0.9900 . ? C21 N3 1.483(4) . ? C21 C22 1.512(4) . ? C21 H17 0.9900 . ? C21 H18 0.9900 . ? C22 O1 1.251(3) . ? C22 N4 1.320(4) . ? O1 La1 2.426(2) . ? N4 C25 1.473(4) . ? N4 C23 1.476(4) . ? C23 C24 1.510(5) . ? C23 H19 0.9900 . ? C23 H20 0.9900 . ? C24 H21 0.9800 . ? C24 H22 0.9800 . ? C24 H23 0.9800 . ? C25 C26 1.516(5) . ? C25 H24 0.9900 . ? C25 H25 0.9900 . ? C26 H26 0.9800 . ? C26 H27 0.9800 . ? C26 H28 0.9800 . ? N3 La1 2.714(2) . ? O2 N5 1.278(3) . ? O2 La1 2.592(2) . ? O3 N5 1.271(3) . ? O3 La1 2.582(2) . ? N5 O4 1.221(3) . ? N5 La1 3.009(3) . ? O5 N6 1.265(3) . ? O5 La1 2.627(2) . ? O6 N6 1.280(3) . ? O6 La1 2.603(2) . ? N6 O7 1.216(3) . ? N6 La1 3.055(3) . ? O8 N7 1.271(3) . ? O8 La1 2.614(2) . ? O9 N7 1.270(3) . ? O9 La1 2.655(2) . ? N7 O10 1.225(3) . ? N7 La1 3.041(2) . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag N1 C1 C9 123.4(3) . . ? N1 C1 C10 117.1(3) . . ? C9 C1 C10 119.3(2) . . ? C1 N1 C2 117.9(2) . . ? C1 N1 La1 115.46(19) . . ? C2 N1 La1 125.64(17) . . ? N1 C2 C3 119.7(3) . . ? N1 C2 C7 121.7(3) . . ? C3 C2 C7 118.5(3) . . ? C4 C3 C2 120.7(3) . . ? C4 C3 H1 119.6 . . ? C2 C3 H1 119.6 . . ? C3 C4 C5 120.8(3) . . ? C3 C4 H2 119.6 . . ? C5 C4 H2 119.6 . . ? C6 C5 C4 119.8(3) . . ? C6 C5 H3 120.1 . . ? C4 C5 H3 120.1 . . ? C5 C6 C7 120.8(3) . . ? C5 C6 H4 119.6 . . ? C7 C6 H4 119.6 . . ? C6 C7 C8 122.7(3) . . ? C6 C7 C2 119.2(3) . . ? C8 C7 C2 118.1(3) . . ? C9 C8 C7 119.4(3) . . ? C9 C8 H5 120.3 . . ? C7 C8 H5 120.3 . . ? C8 C9 C1 119.5(3) . . ? C8 C9 H6 120.2 . . ? C1 C9 H6 120.2 . . ? N3 C10 C1 113.9(2) . . ? N3 C10 H7 108.8 . . ? C1 C10 H7 108.8 . . ? N3 C10 H8 108.8 . . ? C1 C10 H8 108.8 . . ? H7 C10 H8 107.7 . . ? N2 C11 C19 123.5(3) . . ? N2 C11 C20 118.3(3) . . ? C19 C11 C20 118.0(3) . . ? C11 N2 C12 117.6(2) . . ? C11 N2 La1 115.86(19) . . ? C12 N2 La1 126.16(18) . . ? N2 C12 C13 120.0(3) . . ? N2 C12 C17 121.6(3) . . ? C13 C12 C17 118.4(3) . . ? C14 C13 C12 120.4(3) . . ? C14 C13 H9 119.8 . . ? C12 C13 H9 119.8 . . ? C13 C14 C15 121.3(3) . . ? C13 C14 H10 119.3 . . ? C15 C14 H10 119.3 . . ? C16 C15 C14 119.4(3) . . ? C16 C15 H11 120.3 . . ? C14 C15 H11 120.3 . . ? C15 C16 C17 121.2(3) . . ? C15 C16 H12 119.4 . . ? C17 C16 H12 119.4 . . ? C18 C17 C16 122.7(3) . . ? C18 C17 C12 118.1(3) . . ? C16 C17 C12 119.2(3) . . ? C19 C18 C17 119.7(3) . . ? C19 C18 H13 120.1 . . ? C17 C18 H13 120.1 . . ? C18 C19 C11 119.3(3) . . ? C18 C19 H14 120.4 . . ? C11 C19 H14 120.4 . . ? N3 C20 C11 113.4(2) . . ? N3 C20 H15 108.9 . . ? C11 C20 H15 108.9 . . ? N3 C20 H16 108.9 . . ? C11 C20 H16 108.9 . . ? H15 C20 H16 107.7 . . ? N3 C21 C22 110.6(2) . . ? N3 C21 H17 109.5 . . ? C22 C21 H17 109.5 . . ? N3 C21 H18 109.5 . . ? C22 C21 H18 109.5 . . ? H17 C21 H18 108.1 . . ? O1 C22 N4 121.1(3) . . ? O1 C22 C21 117.3(3) . . ? N4 C22 C21 121.5(2) . . ? C22 O1 La1 129.14(19) . . ? C22 N4 C25 117.6(2) . . ? C22 N4 C23 123.2(3) . . ? C25 N4 C23 119.2(3) . . ? N4 C23 C24 112.6(3) . . ? N4 C23 H19 109.1 . . ? C24 C23 H19 109.1 . . ? N4 C23 H20 109.1 . . ? C24 C23 H20 109.1 . . ? H19 C23 H20 107.8 . . ? C23 C24 H21 109.5 . . ? C23 C24 H22 109.5 . . ? H21 C24 H22 109.5 . . ? C23 C24 H23 109.5 . . ? H21 C24 H23 109.5 . . ? H22 C24 H23 109.5 . . ? N4 C25 C26 113.3(3) . . ? N4 C25 H24 108.9 . . ? C26 C25 H24 108.9 . . ? N4 C25 H25 108.9 . . ? C26 C25 H25 108.9 . . ? H24 C25 H25 107.7 . . ? C25 C26 H26 109.5 . . ? C25 C26 H27 109.5 . . ? H26 C26 H27 109.5 . . ? C25 C26 H28 109.5 . . ? H26 C26 H28 109.5 . . ? H27 C26 H28 109.5 . . ? C20 N3 C10 108.2(2) . . ? C20 N3 C21 108.4(2) . . ? C10 N3 C21 109.5(2) . . ? C20 N3 La1 110.71(16) . . ? C10 N3 La1 107.13(16) . . ? C21 N3 La1 112.79(15) . . ? N5 O2 La1 96.10(16) . . ? N5 O3 La1 96.73(16) . . ? O4 N5 O3 121.7(3) . . ? O4 N5 O2 121.4(3) . . ? O3 N5 O2 116.9(2) . . ? O4 N5 La1 172.9(2) . . ? O3 N5 La1 58.46(14) . . ? O2 N5 La1 58.93(14) . . ? N6 O5 La1 97.24(17) . . ? N6 O6 La1 97.94(16) . . ? O7 N6 O5 122.4(3) . . ? O7 N6 O6 121.5(3) . . ? O5 N6 O6 116.1(2) . . ? O7 N6 La1 179.0(2) . . ? O5 N6 La1 58.52(14) . . ? O6 N6 La1 57.55(14) . . ? N7 O8 La1 96.88(15) . . ? N7 O9 La1 94.96(15) . . ? O10 N7 O9 122.0(2) . . ? O10 N7 O8 121.8(2) . . ? O9 N7 O8 116.3(2) . . ? O10 N7 La1 164.00(18) . . ? O9 N7 La1 60.45(13) . . ? O8 N7 La1 58.60(13) . . ? O1 La1 O3 123.00(7) . . ? O1 La1 O2 82.33(7) . . ? O3 La1 O2 49.63(7) . . ? O1 La1 O6 136.85(7) . . ? O3 La1 O6 72.67(7) . . ? O2 La1 O6 122.16(7) . . ? O1 La1 O8 67.05(7) . . ? O3 La1 O8 66.84(7) . . ? O2 La1 O8 67.07(6) . . ? O6 La1 O8 89.14(7) . . ? O1 La1 O5 133.85(7) . . ? O3 La1 O5 102.79(7) . . ? O2 La1 O5 139.15(7) . . ? O6 La1 O5 48.75(7) . . ? O8 La1 O5 136.60(7) . . ? O1 La1 O9 65.57(6) . . ? O3 La1 O9 104.16(6) . . ? O2 La1 O9 114.50(7) . . ? O6 La1 O9 71.69(7) . . ? O8 La1 O9 48.33(6) . . ? O5 La1 O9 100.16(7) . . ? O1 La1 N3 63.11(7) . . ? O3 La1 N3 118.90(7) . . ? O2 La1 N3 76.35(7) . . ? O6 La1 N3 150.03(7) . . ? O8 La1 N3 120.74(7) . . ? O5 La1 N3 101.46(7) . . ? O9 La1 N3 125.20(7) . . ? O1 La1 N1 68.92(7) . . ? O3 La1 N1 168.07(7) . . ? O2 La1 N1 138.45(7) . . ? O6 La1 N1 99.13(7) . . ? O8 La1 N1 122.63(7) . . ? O5 La1 N1 65.43(7) . . ? O9 La1 N1 80.73(7) . . ? N3 La1 N1 64.22(7) . . ? O1 La1 N2 123.62(7) . . ? O3 La1 N2 73.29(7) . . ? O2 La1 N2 71.13(7) . . ? O6 La1 N2 98.92(7) . . ? O8 La1 N2 134.73(7) . . ? O5 La1 N2 71.95(7) . . ? O9 La1 N2 170.54(7) . . ? N3 La1 N2 62.70(7) . . ? N1 La1 N2 100.08(7) . . ? O1 La1 N5 102.04(7) . . ? O3 La1 N5 24.81(7) . . ? O2 La1 N5 24.97(7) . . ? O6 La1 N5 97.18(7) . . ? O8 La1 N5 62.47(7) . . ? O5 La1 N5 123.81(7) . . ? O9 La1 N5 109.34(6) . . ? N3 La1 N5 98.89(7) . . ? N1 La1 N5 162.93(7) . . ? N2 La1 N5 72.32(7) . . ? O1 La1 N7 59.42(6) . . ? O3 La1 N7 88.09(7) . . ? O2 La1 N7 89.92(7) . . ? O6 La1 N7 83.76(7) . . ? O8 La1 N7 24.52(6) . . ? O5 La1 N7 122.45(7) . . ? O9 La1 N7 24.58(6) . . ? N3 La1 N7 122.15(7) . . ? N1 La1 N7 99.80(7) . . ? N2 La1 N7 159.23(7) . . ? N5 La1 N7 86.91(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 C9 C1 N1 C2 1.7(4) . . . . ? C10 C1 N1 C2 -173.4(3) . . . . ? C9 C1 N1 La1 -167.4(2) . . . . ? C10 C1 N1 La1 17.5(3) . . . . ? C1 N1 C2 C3 176.3(3) . . . . ? La1 N1 C2 C3 -15.8(4) . . . . ? C1 N1 C2 C7 -1.8(4) . . . . ? La1 N1 C2 C7 166.2(2) . . . . ? N1 C2 C3 C4 179.7(3) . . . . ? C7 C2 C3 C4 -2.2(4) . . . . ? C2 C3 C4 C5 0.9(5) . . . . ? C3 C4 C5 C6 1.0(5) . . . . ? C4 C5 C6 C7 -1.7(5) . . . . ? C5 C6 C7 C8 179.3(3) . . . . ? C5 C6 C7 C2 0.4(5) . . . . ? N1 C2 C7 C6 179.6(3) . . . . ? C3 C2 C7 C6 1.5(4) . . . . ? N1 C2 C7 C8 0.6(4) . . . . ? C3 C2 C7 C8 -177.4(3) . . . . ? C6 C7 C8 C9 -178.3(3) . . . . ? C2 C7 C8 C9 0.6(4) . . . . ? C7 C8 C9 C1 -0.7(4) . . . . ? N1 C1 C9 C8 -0.5(5) . . . . ? C10 C1 C9 C8 174.5(3) . . . . ? N1 C1 C10 N3 -49.6(4) . . . . ? C9 C1 C10 N3 135.1(3) . . . . ? C19 C11 N2 C12 3.9(4) . . . . ? C20 C11 N2 C12 -172.7(3) . . . . ? C19 C11 N2 La1 -169.7(2) . . . . ? C20 C11 N2 La1 13.8(3) . . . . ? C11 N2 C12 C13 176.5(3) . . . . ? La1 N2 C12 C13 -10.7(4) . . . . ? C11 N2 C12 C17 -1.5(4) . . . . ? La1 N2 C12 C17 171.3(2) . . . . ? N2 C12 C13 C14 -179.6(3) . . . . ? C17 C12 C13 C14 -1.5(5) . . . . ? C12 C13 C14 C15 1.2(5) . . . . ? C13 C14 C15 C16 0.1(5) . . . . ? C14 C15 C16 C17 -1.1(5) . . . . ? C15 C16 C17 C18 -179.1(3) . . . . ? C15 C16 C17 C12 0.8(5) . . . . ? N2 C12 C17 C18 -1.6(4) . . . . ? C13 C12 C17 C18 -179.6(3) . . . . ? N2 C12 C17 C16 178.6(3) . . . . ? C13 C12 C17 C16 0.5(4) . . . . ? C16 C17 C18 C19 -177.7(3) . . . . ? C12 C17 C18 C19 2.5(5) . . . . ? C17 C18 C19 C11 -0.3(5) . . . . ? N2 C11 C19 C18 -3.0(5) . . . . ? C20 C11 C19 C18 173.5(3) . . . . ? N2 C11 C20 N3 -43.7(4) . . . . ? C19 C11 C20 N3 139.5(3) . . . . ? N3 C21 C22 O1 29.9(4) . . . . ? N3 C21 C22 N4 -153.2(3) . . . . ? N4 C22 O1 La1 163.2(2) . . . . ? C21 C22 O1 La1 -19.9(4) . . . . ? O1 C22 N4 C25 -1.7(4) . . . . ? C21 C22 N4 C25 -178.5(3) . . . . ? O1 C22 N4 C23 177.4(3) . . . . ? C21 C22 N4 C23 0.7(5) . . . . ? C22 N4 C23 C24 91.6(4) . . . . ? C25 N4 C23 C24 -89.2(4) . . . . ? C22 N4 C25 C26 -81.3(4) . . . . ? C23 N4 C25 C26 99.5(3) . . . . ? C11 C20 N3 C10 -67.6(3) . . . . ? C11 C20 N3 C21 173.7(2) . . . . ? C11 C20 N3 La1 49.5(3) . . . . ? C1 C10 N3 C20 171.6(2) . . . . ? C1 C10 N3 C21 -70.5(3) . . . . ? C1 C10 N3 La1 52.2(3) . . . . ? C22 C21 N3 C20 -148.6(2) . . . . ? C22 C21 N3 C10 93.6(3) . . . . ? C22 C21 N3 La1 -25.6(3) . . . . ? La1 O3 N5 O4 171.7(2) . . . . ? La1 O3 N5 O2 -8.2(2) . . . . ? La1 O2 N5 O4 -171.7(2) . . . . ? La1 O2 N5 O3 8.2(2) . . . . ? La1 O5 N6 O7 179.4(3) . . . . ? La1 O5 N6 O6 -1.5(3) . . . . ? La1 O6 N6 O7 -179.4(3) . . . . ? La1 O6 N6 O5 1.5(3) . . . . ? La1 O9 N7 O10 161.6(2) . . . . ? La1 O9 N7 O8 -18.7(2) . . . . ? La1 O8 N7 O10 -161.2(2) . . . . ? La1 O8 N7 O9 19.0(2) . . . . ? C22 O1 La1 O3 112.1(2) . . . . ? C22 O1 La1 O2 82.2(2) . . . . ? C22 O1 La1 O6 -147.9(2) . . . . ? C22 O1 La1 O8 150.5(3) . . . . ? C22 O1 La1 O5 -76.1(3) . . . . ? C22 O1 La1 O9 -156.4(3) . . . . ? C22 O1 La1 N3 3.7(2) . . . . ? C22 O1 La1 N1 -67.2(2) . . . . ? C22 O1 La1 N2 21.0(3) . . . . ? C22 O1 La1 N5 97.6(2) . . . . ? C22 O1 La1 N7 176.7(3) . . . . ? N5 O3 La1 O1 -35.72(18) . . . . ? N5 O3 La1 O2 4.74(14) . . . . ? N5 O3 La1 O6 -170.84(17) . . . . ? N5 O3 La1 O8 -74.16(16) . . . . ? N5 O3 La1 O5 150.34(15) . . . . ? N5 O3 La1 O9 -105.55(16) . . . . ? N5 O3 La1 N3 39.36(18) . . . . ? N5 O3 La1 N1 141.5(3) . . . . ? N5 O3 La1 N2 83.90(16) . . . . ? N5 O3 La1 N7 -86.78(16) . . . . ? N5 O2 La1 O1 141.99(16) . . . . ? N5 O2 La1 O3 -4.71(14) . . . . ? N5 O2 La1 O6 0.28(18) . . . . ? N5 O2 La1 O8 73.71(16) . . . . ? N5 O2 La1 O5 -62.10(18) . . . . ? N5 O2 La1 O9 83.32(16) . . . . ? N5 O2 La1 N3 -153.92(17) . . . . ? N5 O2 La1 N1 -172.37(14) . . . . ? N5 O2 La1 N2 -88.49(16) . . . . ? N5 O2 La1 N7 82.86(16) . . . . ? N6 O6 La1 O1 113.45(17) . . . . ? N6 O6 La1 O3 -126.47(18) . . . . ? N6 O6 La1 O2 -130.45(17) . . . . ? N6 O6 La1 O8 167.56(17) . . . . ? N6 O6 La1 O5 -0.88(15) . . . . ? N6 O6 La1 O9 121.62(18) . . . . ? N6 O6 La1 N3 -8.3(3) . . . . ? N6 O6 La1 N1 44.62(18) . . . . ? N6 O6 La1 N2 -57.19(18) . . . . ? N6 O6 La1 N5 -130.33(17) . . . . ? N6 O6 La1 N7 143.59(18) . . . . ? N7 O8 La1 O1 66.23(15) . . . . ? N7 O8 La1 O3 -148.25(17) . . . . ? N7 O8 La1 O2 157.48(17) . . . . ? N7 O8 La1 O6 -76.77(16) . . . . ? N7 O8 La1 O5 -64.10(19) . . . . ? N7 O8 La1 O9 -10.79(14) . . . . ? N7 O8 La1 N3 100.83(16) . . . . ? N7 O8 La1 N1 23.53(18) . . . . ? N7 O8 La1 N2 -178.50(14) . . . . ? N7 O8 La1 N5 -175.33(18) . . . . ? N6 O5 La1 O1 -119.32(16) . . . . ? N6 O5 La1 O3 53.63(17) . . . . ? N6 O5 La1 O2 94.79(18) . . . . ? N6 O5 La1 O6 0.89(16) . . . . ? N6 O5 La1 O8 -16.1(2) . . . . ? N6 O5 La1 O9 -53.56(17) . . . . ? N6 O5 La1 N3 177.11(17) . . . . ? N6 O5 La1 N1 -128.38(18) . . . . ? N6 O5 La1 N2 121.05(18) . . . . ? N6 O5 La1 N5 68.11(18) . . . . ? N6 O5 La1 N7 -42.32(19) . . . . ? N7 O9 La1 O1 -69.51(15) . . . . ? N7 O9 La1 O3 50.64(16) . . . . ? N7 O9 La1 O2 -1.11(17) . . . . ? N7 O9 La1 O6 116.62(16) . . . . ? N7 O9 La1 O8 10.76(14) . . . . ? N7 O9 La1 O5 156.73(15) . . . . ? N7 O9 La1 N3 -91.34(16) . . . . ? N7 O9 La1 N1 -140.48(16) . . . . ? N7 O9 La1 N5 25.28(17) . . . . ? C20 N3 La1 O1 134.8(2) . . . . ? C10 N3 La1 O1 -107.48(19) . . . . ? C21 N3 La1 O1 13.11(18) . . . . ? C20 N3 La1 O3 20.1(2) . . . . ? C10 N3 La1 O3 137.84(17) . . . . ? C21 N3 La1 O3 -101.57(19) . . . . ? C20 N3 La1 O2 46.54(18) . . . . ? C10 N3 La1 O2 164.29(18) . . . . ? C21 N3 La1 O2 -75.12(19) . . . . ? C20 N3 La1 O6 -85.9(2) . . . . ? C10 N3 La1 O6 31.8(3) . . . . ? C21 N3 La1 O6 152.41(18) . . . . ? C20 N3 La1 O8 98.88(19) . . . . ? C10 N3 La1 O8 -143.36(16) . . . . ? C21 N3 La1 O8 -22.8(2) . . . . ? C20 N3 La1 O5 -91.62(19) . . . . ? C10 N3 La1 O5 26.13(18) . . . . ? C21 N3 La1 O5 146.72(19) . . . . ? C20 N3 La1 O9 157.08(17) . . . . ? C10 N3 La1 O9 -85.17(18) . . . . ? C21 N3 La1 O9 35.4(2) . . . . ? C20 N3 La1 N1 -146.9(2) . . . . ? C10 N3 La1 N1 -29.19(16) . . . . ? C21 N3 La1 N1 91.40(19) . . . . ? C20 N3 La1 N2 -29.03(17) . . . . ? C10 N3 La1 N2 88.72(18) . . . . ? C21 N3 La1 N2 -150.7(2) . . . . ? C20 N3 La1 N5 35.71(19) . . . . ? C10 N3 La1 N5 153.47(17) . . . . ? C21 N3 La1 N5 -85.95(19) . . . . ? C20 N3 La1 N7 127.66(18) . . . . ? C10 N3 La1 N7 -114.59(17) . . . . ? C21 N3 La1 N7 6.0(2) . . . . ? C1 N1 La1 O1 76.5(2) . . . . ? C2 N1 La1 O1 -91.7(2) . . . . ? C1 N1 La1 O3 -101.0(4) . . . . ? C2 N1 La1 O3 90.8(4) . . . . ? C1 N1 La1 O2 27.0(3) . . . . ? C2 N1 La1 O2 -141.1(2) . . . . ? C1 N1 La1 O6 -146.7(2) . . . . ? C2 N1 La1 O6 45.2(2) . . . . ? C1 N1 La1 O8 118.5(2) . . . . ? C2 N1 La1 O8 -49.7(2) . . . . ? C1 N1 La1 O5 -110.5(2) . . . . ? C2 N1 La1 O5 81.3(2) . . . . ? C1 N1 La1 O9 143.7(2) . . . . ? C2 N1 La1 O9 -24.4(2) . . . . ? C1 N1 La1 N3 7.1(2) . . . . ? C2 N1 La1 N3 -161.1(2) . . . . ? C1 N1 La1 N2 -45.8(2) . . . . ? C2 N1 La1 N2 146.0(2) . . . . ? C1 N1 La1 N5 16.0(4) . . . . ? C2 N1 La1 N5 -152.1(2) . . . . ? C1 N1 La1 N7 128.2(2) . . . . ? C2 N1 La1 N7 -40.0(2) . . . . ? C11 N2 La1 O1 -8.7(2) . . . . ? C12 N2 La1 O1 178.4(2) . . . . ? C11 N2 La1 O3 -127.6(2) . . . . ? C12 N2 La1 O3 59.5(2) . . . . ? C11 N2 La1 O2 -75.3(2) . . . . ? C12 N2 La1 O2 111.7(2) . . . . ? C11 N2 La1 O6 163.6(2) . . . . ? C12 N2 La1 O6 -9.3(2) . . . . ? C11 N2 La1 O8 -98.7(2) . . . . ? C12 N2 La1 O8 88.4(2) . . . . ? C11 N2 La1 O5 122.5(2) . . . . ? C12 N2 La1 O5 -50.5(2) . . . . ? C11 N2 La1 N3 8.68(19) . . . . ? C12 N2 La1 N3 -164.3(2) . . . . ? C11 N2 La1 N1 62.6(2) . . . . ? C12 N2 La1 N1 -110.3(2) . . . . ? C11 N2 La1 N5 -101.6(2) . . . . ? C12 N2 La1 N5 85.4(2) . . . . ? C11 N2 La1 N7 -100.4(3) . . . . ? C12 N2 La1 N7 86.6(3) . . . . ? O3 N5 La1 O1 149.95(15) . . . . ? O2 N5 La1 O1 -38.61(16) . . . . ? O2 N5 La1 O3 171.4(3) . . . . ? O3 N5 La1 O2 -171.4(3) . . . . ? O3 N5 La1 O6 8.81(16) . . . . ? O2 N5 La1 O6 -179.76(15) . . . . ? O3 N5 La1 O8 94.06(16) . . . . ? O2 N5 La1 O8 -94.51(17) . . . . ? O3 N5 La1 O5 -35.51(18) . . . . ? O2 N5 La1 O5 135.92(15) . . . . ? O3 N5 La1 O9 81.88(16) . . . . ? O2 N5 La1 O9 -106.69(16) . . . . ? O3 N5 La1 N3 -145.81(16) . . . . ? O2 N5 La1 N3 25.62(16) . . . . ? O3 N5 La1 N1 -154.0(2) . . . . ? O2 N5 La1 N1 17.5(3) . . . . ? O3 N5 La1 N2 -88.30(16) . . . . ? O2 N5 La1 N2 83.13(16) . . . . ? O3 N5 La1 N7 92.12(16) . . . . ? O2 N5 La1 N7 -96.45(16) . . . . ? O10 N7 La1 O1 -5.6(7) . . . . ? O9 N7 La1 O1 97.86(16) . . . . ? O8 N7 La1 O1 -101.79(17) . . . . ? O10 N7 La1 O3 125.2(7) . . . . ? O9 N7 La1 O3 -131.40(15) . . . . ? O8 N7 La1 O3 28.95(16) . . . . ? O10 N7 La1 O2 75.5(7) . . . . ? O9 N7 La1 O2 178.99(15) . . . . ? O8 N7 La1 O2 -20.66(16) . . . . ? O10 N7 La1 O6 -162.1(7) . . . . ? O9 N7 La1 O6 -58.63(16) . . . . ? O8 N7 La1 O6 101.72(16) . . . . ? O10 N7 La1 O8 96.2(7) . . . . ? O9 N7 La1 O8 -160.4(2) . . . . ? O10 N7 La1 O5 -130.9(7) . . . . ? O9 N7 La1 O5 -27.44(17) . . . . ? O8 N7 La1 O5 132.91(15) . . . . ? O10 N7 La1 O9 -103.4(7) . . . . ? O8 N7 La1 O9 160.4(2) . . . . ? O10 N7 La1 N3 1.8(7) . . . . ? O9 N7 La1 N3 105.23(16) . . . . ? O8 N7 La1 N3 -94.42(16) . . . . ? O10 N7 La1 N1 -63.8(7) . . . . ? O9 N7 La1 N1 39.60(16) . . . . ? O8 N7 La1 N1 -160.05(15) . . . . ? O10 N7 La1 N2 99.2(7) . . . . ? O9 N7 La1 N2 -157.34(18) . . . . ? O8 N7 La1 N2 3.0(3) . . . . ? O10 N7 La1 N5 100.3(7) . . . . ? O9 N7 La1 N5 -156.20(16) . . . . ? O8 N7 La1 N5 4.15(16) . . . . ? _diffrn_measured_fraction_theta_max 0.983 _diffrn_reflns_theta_full 27.48 _diffrn_measured_fraction_theta_full 0.983 _refine_diff_density_max 0.848 _refine_diff_density_min -0.568 _refine_diff_density_rms 0.082 data_1a _database_code_depnum_ccdc_archive 'CCDC 640620' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_formula_moiety 'C26 H28 N4 O' _chemical_formula_sum 'C26 H28 N4 O' _chemical_formula_weight 412.52 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting triclinic _symmetry_space_group_name_H-M 'P -1' _symmetry_space_group_name_Hall '-P 1' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 9.42340(10) _cell_length_b 9.62400(10) _cell_length_c 13.7241(2) _cell_angle_alpha 75.383(13) _cell_angle_beta 73.862(13) _cell_angle_gamma 71.909(12) _cell_volume 1117.55(10) _cell_formula_units_Z 2 _cell_measurement_temperature 123(2) _cell_measurement_reflns_used 2479 _cell_measurement_theta_min 3.0817 _cell_measurement_theta_max 27.4835 _exptl_crystal_description Prism _exptl_crystal_colour Colorless _exptl_crystal_size_max 0.30 _exptl_crystal_size_mid 0.20 _exptl_crystal_size_min 0.10 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.226 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 440 _exptl_absorpt_coefficient_mu 0.076 _exptl_absorpt_correction_type Multi-scan _exptl_absorpt_correction_T_min 0.9774 _exptl_absorpt_correction_T_max 0.9924 _exptl_absorpt_process_details '(Jacobson, 1998)' _exptl_special_details ; ? ; _diffrn_ambient_temperature 123(2) _diffrn_radiation_wavelength 0.71070 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'Rotating Anode' _diffrn_radiation_monochromator 'Graphite Monochromator' _diffrn_measurement_method \w _diffrn_radiation_detector CCD _diffrn_measurement_device ; Mercury CCD (2x2 bin mode) ; _diffrn_reflns_number 7185 _diffrn_reflns_av_R_equivalents 0.0263 _diffrn_reflns_av_sigmaI/netI 0.0329 _diffrn_reflns_limit_h_min -11 _diffrn_reflns_limit_h_max 8 _diffrn_reflns_limit_k_min -11 _diffrn_reflns_limit_k_max 8 _diffrn_reflns_limit_l_min -16 _diffrn_reflns_limit_l_max 15 _diffrn_reflns_theta_min 3.08 _diffrn_reflns_theta_max 25.00 _reflns_number_total 3826 _reflns_number_gt 3382 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'CrystalClear (Rigaku Corp., 2000)' _computing_cell_refinement 'CrystalClear (Rigaku Corp., 2000)' _computing_data_reduction 'CrystalClear (Rigaku Corp., 2000)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _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^)+(0.0248P)^2^+0.8651P] 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 3826 _refine_ls_number_parameters 282 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0744 _refine_ls_R_factor_gt 0.0620 _refine_ls_wR_factor_ref 0.1196 _refine_ls_wR_factor_gt 0.1150 _refine_ls_goodness_of_fit_ref 1.187 _refine_ls_restrained_S_all 1.187 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group C1 C 0.8936(2) 0.4459(2) 0.29719(16) 0.0245(5) Uani 1 1 d . . . N1 N 0.9762(2) 0.35552(19) 0.23260(13) 0.0231(4) Uani 1 1 d . . . C2 C 1.1297(2) 0.2989(2) 0.23258(15) 0.0218(5) Uani 1 1 d . . . C3 C 1.2218(2) 0.2115(2) 0.15844(16) 0.0244(5) Uani 1 1 d . . . H1 H 1.1767 0.1897 0.1121 0.029 Uiso 1 1 calc R . . C4 C 1.3757(2) 0.1578(2) 0.15282(17) 0.0280(5) Uani 1 1 d . . . H2 H 1.4372 0.1010 0.1015 0.034 Uiso 1 1 calc R . . C5 C 1.4437(3) 0.1859(3) 0.22234(18) 0.0329(6) Uani 1 1 d . . . H3 H 1.5505 0.1466 0.2185 0.040 Uiso 1 1 calc R . . C6 C 1.3572(3) 0.2696(3) 0.29550(18) 0.0324(6) Uani 1 1 d . . . H4 H 1.4039 0.2870 0.3428 0.039 Uiso 1 1 calc R . . C7 C 1.1988(3) 0.3302(2) 0.30127(16) 0.0254(5) Uani 1 1 d . . . C8 C 1.1041(3) 0.4266(3) 0.36987(17) 0.0330(6) Uani 1 1 d . . . H5 H 1.1450 0.4494 0.4181 0.040 Uiso 1 1 calc R . . C9 C 0.9544(3) 0.4863(3) 0.36622(17) 0.0318(5) Uani 1 1 d . . . H6 H 0.8909 0.5547 0.4097 0.038 Uiso 1 1 calc R . . C10 C 0.7276(3) 0.5140(2) 0.29467(17) 0.0278(5) Uani 1 1 d . . . H7 H 0.6989 0.4716 0.2465 0.033 Uiso 1 1 calc R . . H8 H 0.6633 0.4917 0.3642 0.033 Uiso 1 1 calc R . . C11 C 0.7855(2) 0.8652(2) 0.11755(15) 0.0217(5) Uani 1 1 d . . . N2 N 0.72534(19) 0.9554(2) 0.04120(13) 0.0238(4) Uani 1 1 d . . . C12 C 0.7484(2) 1.0958(2) 0.01208(15) 0.0240(5) Uani 1 1 d . . . C13 C 0.6820(3) 1.1935(3) -0.06795(18) 0.0339(6) Uani 1 1 d . . . H9 H 0.6280 1.1600 -0.1026 0.041 Uiso 1 1 calc R . . C14 C 0.6949(3) 1.3362(3) -0.0961(2) 0.0438(7) Uani 1 1 d . . . H10 H 0.6499 1.4015 -0.1503 0.053 Uiso 1 1 calc R . . C15 C 0.7742(3) 1.3871(3) -0.04549(19) 0.0412(6) Uani 1 1 d . . . H11 H 0.7808 1.4873 -0.0649 0.049 Uiso 1 1 calc R . . C16 C 0.8417(3) 1.2944(3) 0.03115(18) 0.0328(5) Uani 1 1 d . . . H12 H 0.8966 1.3297 0.0641 0.039 Uiso 1 1 calc R . . C17 C 0.8306(2) 1.1458(2) 0.06191(16) 0.0239(5) Uani 1 1 d . . . C18 C 0.8957(2) 1.0437(3) 0.14178(16) 0.0268(5) Uani 1 1 d . . . H13 H 0.9546 1.0718 0.1759 0.032 Uiso 1 1 calc R . . C19 C 0.8732(2) 0.9052(2) 0.16922(16) 0.0260(5) Uani 1 1 d . . . H14 H 0.9161 0.8356 0.2228 0.031 Uiso 1 1 calc R . . C20 C 0.7589(3) 0.7121(2) 0.14902(16) 0.0264(5) Uani 1 1 d . . . H15 H 0.6836 0.7071 0.1130 0.032 Uiso 1 1 calc R . . H16 H 0.8559 0.6381 0.1278 0.032 Uiso 1 1 calc R . . N3 N 0.7024(2) 0.67505(19) 0.26088(13) 0.0239(4) Uani 1 1 d . . . C21 C 0.5436(2) 0.7546(2) 0.29151(16) 0.0245(5) Uani 1 1 d . . . H17 H 0.4781 0.7070 0.2728 0.029 Uiso 1 1 calc R . . H18 H 0.5280 0.8580 0.2527 0.029 Uiso 1 1 calc R . . C22 C 0.4935(2) 0.7580(2) 0.40702(16) 0.0227(5) Uani 1 1 d . . . O1 O 0.58205(17) 0.69946(17) 0.46518(11) 0.0294(4) Uani 1 1 d . . . N4 N 0.3464(2) 0.8306(2) 0.44069(14) 0.0251(4) Uani 1 1 d . . . C23 C 0.2352(3) 0.8995(3) 0.37566(19) 0.0376(6) Uani 1 1 d . . . H19 H 0.2900 0.9269 0.3038 0.045 Uiso 1 1 calc R . . H20 H 0.1675 0.9920 0.3990 0.045 Uiso 1 1 calc R . . C24 C 0.1384(4) 0.7988(4) 0.3778(3) 0.0739(11) Uani 1 1 d . . . H21 H 0.2037 0.7112 0.3488 0.111 Uiso 1 1 calc R . . H22 H 0.0611 0.8527 0.3369 0.111 Uiso 1 1 calc R . . H23 H 0.0876 0.7674 0.4492 0.111 Uiso 1 1 calc R . . C25 C 0.2898(3) 0.8435(3) 0.54967(17) 0.0334(6) Uani 1 1 d . . . H24 H 0.3525 0.7604 0.5914 0.040 Uiso 1 1 calc R . . H25 H 0.1831 0.8348 0.5720 0.040 Uiso 1 1 calc R . . C26 C 0.2947(5) 0.9884(4) 0.5698(2) 0.0745(11) Uani 1 1 d . . . H26 H 0.4004 0.9968 0.5492 0.112 Uiso 1 1 calc R . . H27 H 0.2560 0.9916 0.6435 0.112 Uiso 1 1 calc R . . H28 H 0.2310 1.0711 0.5299 0.112 Uiso 1 1 calc 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 C1 0.0313(12) 0.0165(11) 0.0200(11) -0.0002(9) -0.0023(9) -0.0037(9) N1 0.0267(10) 0.0167(9) 0.0219(9) -0.0020(7) -0.0020(8) -0.0041(7) C2 0.0264(11) 0.0159(10) 0.0198(11) -0.0002(8) -0.0016(9) -0.0061(9) C3 0.0277(12) 0.0204(11) 0.0224(11) -0.0023(9) -0.0023(9) -0.0066(9) C4 0.0273(12) 0.0221(12) 0.0285(12) -0.0030(9) 0.0008(10) -0.0053(9) C5 0.0254(12) 0.0300(13) 0.0380(14) 0.0008(11) -0.0061(10) -0.0059(10) C6 0.0354(13) 0.0322(13) 0.0313(13) -0.0004(10) -0.0134(11) -0.0100(11) C7 0.0331(12) 0.0206(11) 0.0206(11) 0.0005(9) -0.0071(9) -0.0067(9) C8 0.0461(15) 0.0306(13) 0.0232(12) -0.0045(10) -0.0124(11) -0.0070(11) C9 0.0431(14) 0.0265(12) 0.0217(11) -0.0087(10) -0.0049(10) -0.0016(11) C10 0.0308(12) 0.0200(11) 0.0264(12) -0.0043(9) 0.0004(10) -0.0039(9) C11 0.0191(10) 0.0236(11) 0.0175(10) -0.0065(9) 0.0019(8) -0.0018(9) N2 0.0237(9) 0.0259(10) 0.0193(9) -0.0050(8) -0.0013(7) -0.0052(8) C12 0.0231(11) 0.0261(12) 0.0186(11) -0.0036(9) 0.0016(9) -0.0063(9) C13 0.0384(14) 0.0366(14) 0.0273(12) -0.0001(10) -0.0115(11) -0.0111(11) C14 0.0581(17) 0.0352(15) 0.0345(14) 0.0094(11) -0.0162(13) -0.0141(13) C15 0.0531(16) 0.0285(14) 0.0379(14) 0.0020(11) -0.0036(12) -0.0169(12) C16 0.0373(14) 0.0310(13) 0.0306(13) -0.0056(10) 0.0002(11) -0.0163(11) C17 0.0211(11) 0.0275(12) 0.0204(11) -0.0060(9) 0.0020(9) -0.0068(9) C18 0.0223(11) 0.0373(14) 0.0221(11) -0.0079(10) -0.0027(9) -0.0096(10) C19 0.0248(11) 0.0295(13) 0.0209(11) -0.0036(9) -0.0051(9) -0.0039(10) C20 0.0298(12) 0.0233(12) 0.0227(11) -0.0073(9) -0.0019(9) -0.0028(9) N3 0.0260(10) 0.0173(9) 0.0218(9) -0.0035(7) 0.0003(8) -0.0013(7) C21 0.0234(11) 0.0212(11) 0.0255(11) -0.0049(9) -0.0038(9) -0.0019(9) C22 0.0224(11) 0.0169(11) 0.0278(11) -0.0043(9) -0.0034(9) -0.0052(9) O1 0.0278(8) 0.0318(9) 0.0271(8) -0.0075(7) -0.0078(7) -0.0022(7) N4 0.0228(10) 0.0221(10) 0.0262(10) -0.0048(8) -0.0006(8) -0.0037(8) C23 0.0234(12) 0.0391(15) 0.0384(14) 0.0061(11) -0.0043(10) -0.0039(11) C24 0.056(2) 0.113(3) 0.064(2) 0.024(2) -0.0320(17) -0.053(2) C25 0.0309(13) 0.0300(13) 0.0282(12) -0.0038(10) 0.0068(10) -0.0052(10) C26 0.118(3) 0.0485(19) 0.0444(18) -0.0274(15) 0.0231(19) -0.025(2) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag C1 N1 1.317(3) . ? C1 C9 1.415(3) . ? C1 C10 1.503(3) . ? N1 C2 1.378(3) . ? C2 C3 1.409(3) . ? C2 C7 1.418(3) . ? C3 C4 1.367(3) . ? C4 C5 1.405(3) . ? C5 C6 1.366(3) . ? C6 C7 1.411(3) . ? C7 C8 1.415(3) . ? C8 C9 1.358(3) . ? C10 N3 1.464(3) . ? C11 N2 1.319(3) . ? C11 C19 1.412(3) . ? C11 C20 1.506(3) . ? N2 C12 1.376(3) . ? C12 C13 1.406(3) . ? C12 C17 1.411(3) . ? C13 C14 1.363(3) . ? C14 C15 1.403(4) . ? C15 C16 1.361(3) . ? C16 C17 1.414(3) . ? C17 C18 1.414(3) . ? C18 C19 1.357(3) . ? C20 N3 1.468(3) . ? N3 C21 1.450(3) . ? C21 C22 1.529(3) . ? C22 O1 1.226(2) . ? C22 N4 1.352(3) . ? N4 C23 1.457(3) . ? N4 C25 1.465(3) . ? C23 C24 1.514(4) . ? C25 C26 1.505(4) . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag N1 C1 C9 123.3(2) . . ? N1 C1 C10 118.27(19) . . ? C9 C1 C10 118.37(19) . . ? C1 N1 C2 117.70(18) . . ? N1 C2 C3 118.30(18) . . ? N1 C2 C7 122.57(19) . . ? C3 C2 C7 119.09(19) . . ? C4 C3 C2 120.4(2) . . ? C3 C4 C5 120.6(2) . . ? C6 C5 C4 120.4(2) . . ? C5 C6 C7 120.4(2) . . ? C6 C7 C8 123.5(2) . . ? C6 C7 C2 119.2(2) . . ? C8 C7 C2 117.3(2) . . ? C9 C8 C7 119.5(2) . . ? C8 C9 C1 119.5(2) . . ? N3 C10 C1 109.00(18) . . ? N2 C11 C19 123.3(2) . . ? N2 C11 C20 117.23(18) . . ? C19 C11 C20 119.52(19) . . ? C11 N2 C12 117.72(18) . . ? N2 C12 C13 118.0(2) . . ? N2 C12 C17 122.47(19) . . ? C13 C12 C17 119.5(2) . . ? C14 C13 C12 120.2(2) . . ? C13 C14 C15 120.4(2) . . ? C16 C15 C14 120.6(2) . . ? C15 C16 C17 120.2(2) . . ? C12 C17 C16 118.9(2) . . ? C12 C17 C18 117.6(2) . . ? C16 C17 C18 123.5(2) . . ? C19 C18 C17 119.4(2) . . ? C18 C19 C11 119.6(2) . . ? N3 C20 C11 111.60(17) . . ? C21 N3 C10 112.48(17) . . ? C21 N3 C20 111.11(16) . . ? C10 N3 C20 110.69(16) . . ? N3 C21 C22 112.98(17) . . ? O1 C22 N4 122.2(2) . . ? O1 C22 C21 121.83(19) . . ? N4 C22 C21 115.97(18) . . ? C22 N4 C23 124.62(19) . . ? C22 N4 C25 119.71(18) . . ? C23 N4 C25 115.67(18) . . ? N4 C23 C24 112.8(2) . . ? N4 C25 C26 112.6(2) . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag C9 C1 N1 C2 -0.4(3) . . . . ? C10 C1 N1 C2 177.25(18) . . . . ? C1 N1 C2 C3 -175.11(19) . . . . ? C1 N1 C2 C7 2.3(3) . . . . ? N1 C2 C3 C4 177.43(19) . . . . ? C7 C2 C3 C4 -0.1(3) . . . . ? C2 C3 C4 C5 1.5(3) . . . . ? C3 C4 C5 C6 -1.1(3) . . . . ? C4 C5 C6 C7 -0.8(3) . . . . ? C5 C6 C7 C8 -175.2(2) . . . . ? C5 C6 C7 C2 2.2(3) . . . . ? N1 C2 C7 C6 -179.2(2) . . . . ? C3 C2 C7 C6 -1.8(3) . . . . ? N1 C2 C7 C8 -1.5(3) . . . . ? C3 C2 C7 C8 175.8(2) . . . . ? C6 C7 C8 C9 176.4(2) . . . . ? C2 C7 C8 C9 -1.1(3) . . . . ? C7 C8 C9 C1 2.9(3) . . . . ? N1 C1 C9 C8 -2.2(3) . . . . ? C10 C1 C9 C8 -179.9(2) . . . . ? N1 C1 C10 N3 -114.8(2) . . . . ? C9 C1 C10 N3 63.0(2) . . . . ? C19 C11 N2 C12 -0.8(3) . . . . ? C20 C11 N2 C12 179.72(18) . . . . ? C11 N2 C12 C13 -178.8(2) . . . . ? C11 N2 C12 C17 -1.2(3) . . . . ? N2 C12 C13 C14 176.7(2) . . . . ? C17 C12 C13 C14 -1.1(3) . . . . ? C12 C13 C14 C15 -0.1(4) . . . . ? C13 C14 C15 C16 1.2(4) . . . . ? C14 C15 C16 C17 -1.0(4) . . . . ? N2 C12 C17 C16 -176.4(2) . . . . ? C13 C12 C17 C16 1.1(3) . . . . ? N2 C12 C17 C18 2.6(3) . . . . ? C13 C12 C17 C18 -179.8(2) . . . . ? C15 C16 C17 C12 -0.1(3) . . . . ? C15 C16 C17 C18 -179.0(2) . . . . ? C12 C17 C18 C19 -1.9(3) . . . . ? C16 C17 C18 C19 177.0(2) . . . . ? C17 C18 C19 C11 0.1(3) . . . . ? N2 C11 C19 C18 1.4(3) . . . . ? C20 C11 C19 C18 -179.19(19) . . . . ? N2 C11 C20 N3 -129.9(2) . . . . ? C19 C11 C20 N3 50.6(3) . . . . ? C1 C10 N3 C21 -158.70(17) . . . . ? C1 C10 N3 C20 76.4(2) . . . . ? C11 C20 N3 C21 74.1(2) . . . . ? C11 C20 N3 C10 -160.15(17) . . . . ? C10 N3 C21 C22 72.7(2) . . . . ? C20 N3 C21 C22 -162.54(17) . . . . ? N3 C21 C22 O1 0.7(3) . . . . ? N3 C21 C22 N4 179.99(17) . . . . ? O1 C22 N4 C23 -178.7(2) . . . . ? C21 C22 N4 C23 2.1(3) . . . . ? O1 C22 N4 C25 1.3(3) . . . . ? C21 C22 N4 C25 -178.02(19) . . . . ? C22 N4 C23 C24 94.9(3) . . . . ? C25 N4 C23 C24 -85.0(3) . . . . ? C22 N4 C25 C26 96.0(3) . . . . ? C23 N4 C25 C26 -84.0(3) . . . . ? _diffrn_measured_fraction_theta_max 0.972 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 0.972 _refine_diff_density_max 0.333 _refine_diff_density_min -0.312 _refine_diff_density_rms 0.037