Supplementary Material (ESI) for Dalton Transactions This journal is © The Royal Society of Chemistry 2005 data_global _journal_coden_Cambridge 222 loop_ _publ_author_name 'M. Albrecht' 'Roland Frohlich' 'Olga Ossetska' _publ_contact_author_name 'ProfD M Albrecht' _publ_contact_author_address ; Institut fur Organische Chemie RWTH-Aachen Landoltweg 1 Aachen D-52074 GERMANY ; _publ_contact_author_email MARKUS.ALBRECHT@OC.RWTH-AACHEN.DE _publ_requested_journal 'Dalton Transactions' _publ_section_title ; 2-[(8-Hydroxyquinolinyl)methylene]hydrazinecarboxamide: Expanding the coordination sphere of 8-hydroxyquinoline for coordination of rare-earth metal(III) ions ; data_fro3207 _database_code_depnum_ccdc_archive 'CCDC 273595' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C28 H32 Eu2 N15 Na1 O21' _chemical_formula_weight 1241.60 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' Na Na 0.0362 0.0249 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting tetragonal _symmetry_space_group_name_H-M I41/a loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, -y, z+1/2' '-y+3/4, x+1/4, z+1/4' 'y+3/4, -x+3/4, z+3/4' 'x+1/2, y+1/2, z+1/2' '-x+1, -y+1/2, z+1' '-y+5/4, x+3/4, z+3/4' 'y+5/4, -x+5/4, z+5/4' '-x, -y, -z' 'x-1/2, y, -z-1/2' 'y-3/4, -x-1/4, -z-1/4' '-y-3/4, x-3/4, -z-3/4' '-x+1/2, -y+1/2, -z+1/2' 'x, y+1/2, -z' 'y-1/4, -x+1/4, -z+1/4' '-y-1/4, x-1/4, -z-1/4' _cell_length_a 17.752(1) _cell_length_b 17.752(1) _cell_length_c 29.372(1) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 9256.1(8) _cell_formula_units_Z 8 _cell_measurement_temperature 198(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description block _exptl_crystal_colour orange _exptl_crystal_size_max 0.20 _exptl_crystal_size_mid 0.10 _exptl_crystal_size_min 0.10 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.782 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 4880 _exptl_absorpt_coefficient_mu 2.786 _exptl_absorpt_correction_type empirical _exptl_absorpt_correction_T_min 0.6057 _exptl_absorpt_correction_T_max 0.7681 _exptl_absorpt_process_details 'SORTAV (BLessing, 1995 & 1997)' _exptl_special_details ; ? ; _diffrn_ambient_temperature 198(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'rotating anode Nonius FR591' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Nonius KappaCCD' _diffrn_measurement_method '\w and \f scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 35469 _diffrn_reflns_av_R_equivalents 0.0572 _diffrn_reflns_av_sigmaI/netI 0.0388 _diffrn_reflns_limit_h_min -21 _diffrn_reflns_limit_h_max 18 _diffrn_reflns_limit_k_min -22 _diffrn_reflns_limit_k_max 23 _diffrn_reflns_limit_l_min -38 _diffrn_reflns_limit_l_max 28 _diffrn_reflns_theta_min 2.13 _diffrn_reflns_theta_max 27.86 _reflns_number_total 5512 _reflns_number_gt 4081 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Collect (Nonius B.V., 1998)' _computing_cell_refinement 'Collect (Nonius B.V., 1998)' _computing_data_reduction 'Denzo-SMN (Otwinowski & Minor, 1997)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'SCHAKAL (Keller, 1997)' _computing_publication_material '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. Sodium ion is distributed over three close positions, using isotropic thermal displacement parameters. ; _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^)+(0.0661P)^2^+48.8152P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens 'at N from difmap, other geom' _refine_ls_hydrogen_treatment mixed _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 5512 _refine_ls_number_parameters 313 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0769 _refine_ls_R_factor_gt 0.0483 _refine_ls_wR_factor_ref 0.1354 _refine_ls_wR_factor_gt 0.1226 _refine_ls_goodness_of_fit_ref 1.057 _refine_ls_restrained_S_all 1.057 _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 Eu Eu 0.642190(15) 0.282584(15) 0.122179(9) 0.03879(12) Uani 1 1 d . . . N11 N 0.6613(2) 0.3956(2) 0.06083(14) 0.0349(10) Uani 1 1 d . . . C12 C 0.6093(3) 0.4032(3) 0.02707(18) 0.0399(12) Uani 1 1 d . . . C13 C 0.5506(3) 0.3487(3) 0.02577(18) 0.0379(12) Uani 1 1 d . . . O13 O 0.55128(18) 0.2950(2) 0.05820(12) 0.0335(8) Uani 1 1 d . . . C14 C 0.4976(4) 0.3543(4) -0.0075(2) 0.0570(17) Uani 1 1 d . . . H14 H 0.4571 0.3193 -0.0083 0.068 Uiso 1 1 calc R . . C15 C 0.5018(5) 0.4107(5) -0.0404(3) 0.086(3) Uani 1 1 d . . . H15 H 0.4647 0.4123 -0.0637 0.103 Uiso 1 1 calc R . . C16 C 0.5579(5) 0.4640(5) -0.0402(3) 0.080(3) Uani 1 1 d . . . H16 H 0.5587 0.5029 -0.0624 0.096 Uiso 1 1 calc R . . C17 C 0.6134(4) 0.4600(4) -0.0070(2) 0.0562(17) Uani 1 1 d . . . C18 C 0.6748(4) 0.5116(4) -0.0028(2) 0.0627(19) Uani 1 1 d . . . H18 H 0.6790 0.5524 -0.0235 0.075 Uiso 1 1 calc R . . C19 C 0.7264(4) 0.5029(4) 0.0300(2) 0.0568(17) Uani 1 1 d . . . H19 H 0.7681 0.5364 0.0319 0.068 Uiso 1 1 calc R . . C20 C 0.7186(3) 0.4438(3) 0.0618(2) 0.0457(14) Uani 1 1 d . . . C21 C 0.7717(3) 0.4335(3) 0.0995(2) 0.0482(15) Uani 1 1 d . . . H21 H 0.8150 0.4646 0.1022 0.058 Uiso 1 1 calc R . . N22 N 0.7586(3) 0.3821(3) 0.12847(15) 0.0416(11) Uani 1 1 d . . . N23 N 0.8055(3) 0.3732(3) 0.16484(18) 0.0571(15) Uani 1 1 d . . . H23A H 0.8483 0.3979 0.1669 0.069 Uiso 1 1 calc R . . C24 C 0.7832(4) 0.3246(4) 0.1975(2) 0.0516(16) Uani 1 1 d . . . N25 N 0.8254(3) 0.3197(3) 0.2345(2) 0.0712(19) Uani 1 1 d . . . H25A H 0.8124 0.2888 0.2565 0.085 Uiso 1 1 calc R . . H25B H 0.8663 0.3472 0.2370 0.085 Uiso 1 1 calc R . . O26 O 0.7243(2) 0.2860(2) 0.19272(13) 0.0480(10) Uani 1 1 d . . . N31 N 0.7613(3) 0.2074(3) 0.0604(3) 0.0646(17) Uani 1 1 d . . . O32 O 0.7125(3) 0.2553(3) 0.04417(18) 0.0766(16) Uani 1 1 d . . . O33 O 0.7704(3) 0.2018(3) 0.0979(2) 0.0669(14) Uani 1 1 d . . . O34 O 0.7966(4) 0.1712(3) 0.0284(2) 0.100(2) Uani 1 1 d . . . N41 N 0.6348(3) 0.1117(3) 0.12738(19) 0.0505(13) Uani 1 1 d . . . O42 O 0.6141(3) 0.1457(2) 0.09165(15) 0.0539(11) Uani 1 1 d . . . O43 O 0.6507(3) 0.1483(2) 0.16131(15) 0.0617(13) Uani 1 1 d . . . O44 O 0.6393(4) 0.0418(3) 0.1284(2) 0.093(2) Uani 1 1 d . . . N51 N 0.5000 0.2500 0.1865(2) 0.0409(15) Uani 1 2 d S . . O52 O 0.5000 0.2500 0.14307(17) 0.0395(12) Uani 1 2 d S . . O53 O 0.4398(3) 0.2382(3) 0.20607(14) 0.0595(12) Uani 1 1 d . . . O61 O 0.5892(3) 0.4001(2) 0.15276(16) 0.0582(11) Uani 1 1 d . . . C62 C 0.5404(4) 0.4397(4) 0.1737(4) 0.098(4) Uani 1 1 d . . . H62 H 0.5031 0.4161 0.1920 0.118 Uiso 1 1 calc R . . N63 N 0.5422(5) 0.5143(4) 0.1696(3) 0.092(2) Uani 1 1 d . . . C64 C 0.4875(9) 0.5626(7) 0.1825(5) 0.150(5) Uani 1 1 d . . . H64A H 0.4397 0.5354 0.1852 0.224 Uiso 1 1 calc R . . H64B H 0.4825 0.6026 0.1598 0.224 Uiso 1 1 calc R . . H64C H 0.5007 0.5848 0.2120 0.224 Uiso 1 1 calc R . . C65 C 0.6129(10) 0.5513(8) 0.1508(7) 0.193(8) Uani 1 1 d . . . H65A H 0.6573 0.5229 0.1607 0.289 Uiso 1 1 calc R . . H65B H 0.6163 0.6031 0.1622 0.289 Uiso 1 1 calc R . . H65C H 0.6107 0.5518 0.1175 0.289 Uiso 1 1 calc R . . Na1 Na 1.024(3) 0.292(3) 0.175(2) 0.202(19) Uiso 0.16 1 d P . . Na2 Na 1.082(3) 0.328(2) 0.1859(15) 0.205(15) Uiso 0.21 1 d P . . Na3 Na 0.988(5) 0.271(4) 0.1437(19) 0.20(3) Uiso 0.13 1 d P . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 Eu 0.03754(18) 0.03759(17) 0.04126(19) 0.00206(12) -0.00891(11) -0.00615(11) N11 0.041(2) 0.035(2) 0.029(2) 0.0048(18) -0.0046(18) -0.0128(19) C12 0.046(3) 0.040(3) 0.033(3) 0.011(2) -0.004(2) -0.009(2) C13 0.035(3) 0.048(3) 0.031(3) 0.009(2) -0.003(2) -0.009(2) O13 0.0274(17) 0.043(2) 0.0301(18) 0.0073(15) -0.0042(14) -0.0111(14) C14 0.050(4) 0.074(4) 0.047(4) 0.021(3) -0.015(3) -0.020(3) C15 0.070(5) 0.122(7) 0.065(5) 0.049(5) -0.035(4) -0.031(5) C16 0.081(5) 0.099(6) 0.061(5) 0.050(4) -0.024(4) -0.031(5) C17 0.056(4) 0.065(4) 0.048(4) 0.027(3) -0.009(3) -0.015(3) C18 0.074(5) 0.060(4) 0.054(4) 0.028(3) -0.011(3) -0.026(3) C19 0.067(4) 0.051(4) 0.052(4) 0.021(3) -0.012(3) -0.029(3) C20 0.051(3) 0.043(3) 0.043(3) 0.008(3) -0.009(3) -0.018(3) C21 0.048(3) 0.047(3) 0.050(3) 0.008(3) -0.014(3) -0.023(3) N22 0.042(3) 0.041(3) 0.042(3) 0.005(2) -0.020(2) -0.018(2) N23 0.053(3) 0.061(3) 0.057(3) 0.016(3) -0.030(3) -0.035(3) C24 0.053(4) 0.051(3) 0.051(4) 0.007(3) -0.026(3) -0.013(3) N25 0.070(4) 0.075(4) 0.068(4) 0.032(3) -0.044(3) -0.036(3) O26 0.051(2) 0.052(2) 0.040(2) 0.0130(18) -0.0236(18) -0.0200(19) N31 0.045(3) 0.037(3) 0.112(6) -0.009(3) 0.006(4) 0.020(2) O32 0.086(4) 0.076(3) 0.067(3) 0.013(3) 0.018(3) 0.044(3) O33 0.048(3) 0.061(3) 0.091(4) 0.014(3) -0.019(3) 0.010(2) O34 0.097(4) 0.080(4) 0.124(5) -0.019(4) 0.021(4) 0.048(3) N41 0.047(3) 0.034(3) 0.070(4) 0.003(2) -0.018(3) -0.005(2) O42 0.064(3) 0.040(2) 0.058(3) -0.007(2) -0.024(2) 0.0037(19) O43 0.096(4) 0.042(2) 0.047(3) 0.006(2) -0.023(2) -0.023(2) O44 0.126(5) 0.035(3) 0.119(5) -0.002(3) -0.058(4) -0.003(3) N51 0.041(4) 0.049(4) 0.033(3) 0.000 0.000 -0.009(3) O52 0.038(3) 0.054(3) 0.025(3) 0.000 0.000 -0.014(2) O53 0.051(3) 0.090(4) 0.037(2) -0.003(2) 0.010(2) -0.014(2) O61 0.064(3) 0.048(3) 0.062(3) -0.015(2) 0.013(2) -0.004(2) C62 0.049(4) 0.046(4) 0.200(11) -0.049(6) -0.010(5) 0.001(3) N63 0.112(6) 0.078(5) 0.085(5) -0.023(4) -0.019(5) 0.011(4) C64 0.191(14) 0.105(9) 0.152(12) -0.041(8) 0.004(11) 0.061(9) C65 0.191(17) 0.121(12) 0.27(2) 0.014(13) -0.050(16) -0.079(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 Eu O61 2.459(4) . ? Eu O13 2.487(3) . ? Eu O26 2.534(4) . ? Eu O42 2.637(4) . ? Eu O43 2.651(4) . ? Eu O32 2.654(5) . ? Eu O52 2.6613(12) . ? Eu N11 2.717(4) . ? Eu N22 2.724(4) . ? Eu O33 2.783(5) . ? Eu O53 2.886(4) 6_554 ? Eu N41 3.040(5) . ? N11 C20 1.329(7) . ? N11 C12 1.361(7) . ? C12 C13 1.422(7) . ? C12 C17 1.422(8) . ? C13 O13 1.347(6) . ? C13 C14 1.362(8) . ? C14 C15 1.393(9) . ? C15 C16 1.374(11) . ? C16 C17 1.389(9) . ? C17 C18 1.427(9) . ? C18 C19 1.340(9) . ? C19 C20 1.412(8) . ? C20 C21 1.467(8) . ? C21 N22 1.269(7) . ? N22 N23 1.364(6) . ? N23 C24 1.348(8) . ? C24 O26 1.259(7) . ? C24 N25 1.322(7) . ? N31 O33 1.120(8) . ? N31 O34 1.299(8) . ? N31 O32 1.304(7) . ? N41 O43 1.222(6) . ? N41 O44 1.245(7) . ? N41 O42 1.265(6) . ? N51 O53 1.231(5) 6_554 ? N51 O53 1.231(5) . ? N51 O52 1.276(8) . ? O52 Eu 2.6613(12) 6_554 ? O53 Eu 2.886(4) 6_554 ? O61 C62 1.274(9) . ? C62 N63 1.331(11) . ? N63 C64 1.350(13) . ? N63 C65 1.519(18) . ? Na1 Na3 1.18(8) . ? Na1 Na2 1.25(6) . ? Na1 Na3 1.46(9) 6_654 ? Na1 Na1 1.70(12) 6_654 ? Na1 Na3 2.10(10) 15_665 ? Na1 Na3 2.38(9) 12_756 ? Na1 Na2 2.84(9) 6_654 ? Na1 Na1 3.19(12) 15_665 ? Na1 Na1 3.19(12) 12_756 ? Na1 Na2 3.79(8) 12_756 ? Na1 Na2 4.04(7) 15_665 ? Na2 Na3 2.30(10) . ? Na2 Na3 2.47(10) 6_654 ? Na2 Na3 2.82(9) 15_665 ? Na2 Na1 2.84(9) 6_654 ? Na2 Na3 3.36(7) 12_756 ? Na2 Na1 3.79(8) 15_665 ? Na2 Na2 3.99(9) 6_654 ? Na2 Na1 4.04(7) 12_756 ? Na3 Na3 0.86(14) 6_654 ? Na3 Na3 1.26(10) 12_756 ? Na3 Na3 1.26(10) 15_665 ? Na3 Na1 1.46(9) 6_654 ? Na3 Na1 2.10(10) 12_756 ? Na3 Na1 2.38(9) 15_665 ? Na3 Na2 2.47(10) 6_654 ? Na3 Na2 2.82(9) 12_756 ? Na3 Na2 3.36(7) 15_665 ? 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 O61 Eu O13 87.27(14) . . ? O61 Eu O26 84.31(16) . . ? O13 Eu O26 171.48(14) . . ? O61 Eu O42 146.50(15) . . ? O13 Eu O42 72.69(12) . . ? O26 Eu O42 114.13(13) . . ? O61 Eu O43 128.80(16) . . ? O13 Eu O43 116.39(12) . . ? O26 Eu O43 68.55(13) . . ? O42 Eu O43 47.91(13) . . ? O61 Eu O32 130.55(16) . . ? O13 Eu O32 70.67(14) . . ? O26 Eu O32 116.10(16) . . ? O42 Eu O32 68.11(17) . . ? O43 Eu O32 100.58(16) . . ? O61 Eu O52 74.78(11) . . ? O13 Eu O52 65.04(13) . . ? O26 Eu O52 111.23(14) . . ? O42 Eu O52 72.49(11) . . ? O43 Eu O52 76.02(12) . . ? O32 Eu O52 127.27(17) . . ? O61 Eu N11 70.34(15) . . ? O13 Eu N11 60.93(11) . . ? O26 Eu N11 116.94(12) . . ? O42 Eu N11 118.55(13) . . ? O43 Eu N11 160.77(15) . . ? O32 Eu N11 60.23(15) . . ? O52 Eu N11 115.56(12) . . ? O61 Eu N22 73.45(16) . . ? O13 Eu N22 119.06(12) . . ? O26 Eu N22 59.53(12) . . ? O42 Eu N22 139.77(15) . . ? O43 Eu N22 120.70(14) . . ? O32 Eu N22 79.63(17) . . ? O52 Eu N22 147.62(12) . . ? N11 Eu N22 58.14(13) . . ? O61 Eu O33 147.53(15) . . ? O13 Eu O33 112.54(15) . . ? O26 Eu O33 75.59(17) . . ? O42 Eu O33 65.97(15) . . ? O43 Eu O33 66.49(17) . . ? O32 Eu O33 45.60(17) . . ? O52 Eu O33 136.28(11) . . ? N11 Eu O33 96.24(15) . . ? N22 Eu O33 74.40(16) . . ? O61 Eu O53 66.66(15) . 6_554 ? O13 Eu O53 109.22(11) . 6_554 ? O26 Eu O53 66.11(13) . 6_554 ? O42 Eu O53 94.42(15) . 6_554 ? O43 Eu O53 62.82(16) . 6_554 ? O32 Eu O53 162.02(16) . 6_554 ? O52 Eu O53 45.31(13) . 6_554 ? N11 Eu O53 136.35(14) . 6_554 ? N22 Eu O53 114.07(13) . 6_554 ? O33 Eu O53 124.41(16) . 6_554 ? O61 Eu N41 144.30(15) . . ? O13 Eu N41 95.67(13) . . ? O26 Eu N41 90.43(13) . . ? O42 Eu N41 24.46(13) . . ? O43 Eu N41 23.55(13) . . ? O32 Eu N41 83.20(16) . . ? O52 Eu N41 74.39(10) . . ? N11 Eu N41 140.82(14) . . ? N22 Eu N41 132.53(14) . . ? O33 Eu N41 62.21(15) . . ? O53 Eu N41 78.90(15) 6_554 . ? C20 N11 C12 118.0(4) . . ? C20 N11 Eu 123.8(3) . . ? C12 N11 Eu 118.2(3) . . ? N11 C12 C13 116.6(5) . . ? N11 C12 C17 123.2(5) . . ? C13 C12 C17 120.1(5) . . ? O13 C13 C14 124.4(5) . . ? O13 C13 C12 117.1(4) . . ? C14 C13 C12 118.4(5) . . ? C13 O13 Eu 127.1(3) . . ? C13 C14 C15 120.9(6) . . ? C16 C15 C14 122.0(6) . . ? C15 C16 C17 118.9(6) . . ? C16 C17 C12 119.6(6) . . ? C16 C17 C18 124.7(6) . . ? C12 C17 C18 115.7(5) . . ? C19 C18 C17 120.7(6) . . ? C18 C19 C20 119.5(6) . . ? N11 C20 C19 122.7(5) . . ? N11 C20 C21 115.4(5) . . ? C19 C20 C21 121.9(5) . . ? N22 C21 C20 118.5(5) . . ? C21 N22 N23 119.7(4) . . ? C21 N22 Eu 124.1(3) . . ? N23 N22 Eu 116.2(3) . . ? C24 N23 N22 116.8(4) . . ? O26 C24 N25 121.7(6) . . ? O26 C24 N23 120.9(5) . . ? N25 C24 N23 117.4(5) . . ? C24 O26 Eu 125.6(4) . . ? O33 N31 O34 126.8(6) . . ? O33 N31 O32 120.9(6) . . ? O34 N31 O32 112.3(7) . . ? O33 N31 Eu 63.8(4) . . ? O34 N31 Eu 165.6(5) . . ? O32 N31 Eu 58.5(3) . . ? N31 O32 Eu 96.7(4) . . ? N31 O33 Eu 95.1(4) . . ? O43 N41 O44 119.7(5) . . ? O43 N41 O42 119.3(5) . . ? O44 N41 O42 121.0(5) . . ? O43 N41 Eu 60.1(3) . . ? O44 N41 Eu 173.7(5) . . ? O42 N41 Eu 59.6(3) . . ? N41 O42 Eu 95.9(3) . . ? N41 O43 Eu 96.4(3) . . ? O53 N51 O53 124.3(7) 6_554 . ? O53 N51 O52 117.8(3) 6_554 . ? O53 N51 O52 117.8(3) . . ? N51 O52 Eu 103.33(11) . . ? N51 O52 Eu 103.33(11) . 6_554 ? Eu O52 Eu 153.3(2) . 6_554 ? N51 O53 Eu 93.5(3) . 6_554 ? C62 O61 Eu 154.7(5) . . ? O61 C62 N63 119.2(9) . . ? C62 N63 C64 126.1(11) . . ? C62 N63 C65 118.9(10) . . ? C64 N63 C65 114.9(11) . . ? Na3 Na1 Na2 143(8) . . ? Na3 Na1 Na3 36(6) . 6_654 ? Na2 Na1 Na3 132(6) . 6_654 ? Na3 Na1 Na1 58(5) . 6_654 ? Na2 Na1 Na1 148(6) . 6_654 ? Na3 Na1 Na1 43(4) 6_654 6_654 ? Na3 Na1 Na3 32(5) . 15_665 ? Na2 Na1 Na3 113(4) . 15_665 ? Na3 Na1 Na3 36(3) 6_654 15_665 ? Na1 Na1 Na3 77(3) 6_654 15_665 ? Na3 Na1 Na3 13(5) . 12_756 ? Na2 Na1 Na3 134(5) . 12_756 ? Na3 Na1 Na3 27(3) 6_654 12_756 ? Na1 Na1 Na3 59(2) 6_654 12_756 ? Na3 Na1 Na3 21(4) 15_665 12_756 ? Na3 Na1 Na2 60(5) . 6_654 ? Na2 Na1 Na2 153(5) . 6_654 ? Na3 Na1 Na2 54(4) 6_654 6_654 ? Na1 Na1 Na2 13(3) 6_654 6_654 ? Na3 Na1 Na2 85(3) 15_665 6_654 ? Na3 Na1 Na2 65(2) 12_756 6_654 ? Na3 Na1 Na1 38(5) . 15_665 ? Na2 Na1 Na1 110(4) . 15_665 ? Na3 Na1 Na1 32(3) 6_654 15_665 ? Na1 Na1 Na1 74.5(10) 6_654 15_665 ? Na3 Na1 Na1 10(3) 15_665 15_665 ? Na3 Na1 Na1 25.5(18) 12_756 15_665 ? Na2 Na1 Na1 84.0(18) 6_654 15_665 ? Na3 Na1 Na1 18(5) . 12_756 ? Na2 Na1 Na1 126(5) . 12_756 ? Na3 Na1 Na1 44(3) 6_654 12_756 ? Na1 Na1 Na1 74.5(10) 6_654 12_756 ? Na3 Na1 Na1 22(2) 15_665 12_756 ? Na3 Na1 Na1 18(3) 12_756 12_756 ? Na2 Na1 Na1 77.8(17) 6_654 12_756 ? Na1 Na1 Na1 31(2) 15_665 12_756 ? Na3 Na1 Na2 29(5) . 12_756 ? Na2 Na1 Na2 121(4) . 12_756 ? Na3 Na1 Na2 62(3) 6_654 12_756 ? Na1 Na1 Na2 86(2) 6_654 12_756 ? Na3 Na1 Na2 37(3) 15_665 12_756 ? Na3 Na1 Na2 35(3) 12_756 12_756 ? Na2 Na1 Na2 85.5(18) 6_654 12_756 ? Na1 Na1 Na2 47.0(15) 15_665 12_756 ? Na1 Na1 Na2 18.1(12) 12_756 12_756 ? Na3 Na1 Na2 48(5) . 15_665 ? Na2 Na1 Na2 106(4) . 15_665 ? Na3 Na1 Na2 27(4) 6_654 15_665 ? Na1 Na1 Na2 69(2) 6_654 15_665 ? Na3 Na1 Na2 24(3) 15_665 15_665 ? Na3 Na1 Na2 34(3) 12_756 15_665 ? Na2 Na1 Na2 80.9(17) 6_654 15_665 ? Na1 Na1 Na2 14.5(11) 15_665 15_665 ? Na1 Na1 Na2 44.3(13) 12_756 15_665 ? Na2 Na1 Na2 61.2(14) 12_756 15_665 ? Na1 Na2 Na3 18(4) . . ? Na1 Na2 Na3 26(3) . 6_654 ? Na3 Na2 Na3 20(3) . 6_654 ? Na1 Na2 Na3 43(3) . 15_665 ? Na3 Na2 Na3 26(2) . 15_665 ? Na3 Na2 Na3 26(2) 6_654 15_665 ? Na1 Na2 Na1 18(4) . 6_654 ? Na3 Na2 Na1 31(2) . 6_654 ? Na3 Na2 Na1 24.4(18) 6_654 6_654 ? Na3 Na2 Na1 49.6(17) 15_665 6_654 ? Na1 Na2 Na3 31(4) . 12_756 ? Na3 Na2 Na3 14(3) . 12_756 ? Na3 Na2 Na3 18(2) 6_654 12_756 ? Na3 Na2 Na3 13(2) 15_665 12_756 ? Na1 Na2 Na3 38(2) 6_654 12_756 ? Na1 Na2 Na1 52(4) . 15_665 ? Na3 Na2 Na1 36(2) . 15_665 ? Na3 Na2 Na1 31(2) 6_654 15_665 ? Na3 Na2 Na1 12(2) 15_665 15_665 ? Na1 Na2 Na1 55.2(19) 6_654 15_665 ? Na3 Na2 Na1 22.6(13) 12_756 15_665 ? Na1 Na2 Na2 19(3) . 6_654 ? Na3 Na2 Na2 35(2) . 6_654 ? Na3 Na2 Na2 32(2) 6_654 6_654 ? Na3 Na2 Na2 56.0(15) 15_665 6_654 ? Na1 Na2 Na2 8.0(15) 6_654 6_654 ? Na3 Na2 Na2 44.1(14) 12_756 6_654 ? Na1 Na2 Na2 62.5(11) 15_665 6_654 ? Na1 Na2 Na1 40(4) . 12_756 ? Na3 Na2 Na1 22.0(19) . 12_756 ? Na3 Na2 Na1 32.8(18) 6_654 12_756 ? Na3 Na2 Na1 14(2) 15_665 12_756 ? Na1 Na2 Na1 51.7(18) 6_654 12_756 ? Na3 Na2 Na1 15.0(15) 12_756 12_756 ? Na1 Na2 Na1 24.8(16) 15_665 12_756 ? Na2 Na2 Na1 56.3(9) 6_654 12_756 ? Na3 Na3 Na1 90(9) 6_654 . ? Na3 Na3 Na3 70(3) 6_654 12_756 ? Na1 Na3 Na3 154(10) . 12_756 ? Na3 Na3 Na3 70(3) 6_654 15_665 ? Na1 Na3 Na3 119(9) . 15_665 ? Na3 Na3 Na3 40(7) 12_756 15_665 ? Na3 Na3 Na1 54(7) 6_654 6_654 ? Na1 Na3 Na1 79(7) . 6_654 ? Na3 Na3 Na1 100(6) 12_756 6_654 ? Na3 Na3 Na1 121(6) 15_665 6_654 ? Na3 Na3 Na1 98(4) 6_654 12_756 ? Na1 Na3 Na1 153(8) . 12_756 ? Na3 Na3 Na1 30(5) 12_756 12_756 ? Na3 Na3 Na1 43(4) 15_665 12_756 ? Na1 Na3 Na1 126(5) 6_654 12_756 ? Na3 Na3 Na2 91(10) 6_654 . ? Na1 Na3 Na2 19(4) . . ? Na3 Na3 Na2 140(8) 12_756 . ? Na3 Na3 Na2 101(7) 15_665 . ? Na1 Na3 Na2 95(5) 6_654 . ? Na1 Na3 Na2 134(4) 12_756 . ? Na3 Na3 Na1 61(4) 6_654 15_665 ? Na1 Na3 Na1 124(7) . 15_665 ? Na3 Na3 Na1 32(4) 12_756 15_665 ? Na3 Na3 Na1 12(5) 15_665 15_665 ? Na1 Na3 Na1 110(4) 6_654 15_665 ? Na1 Na3 Na1 44(3) 12_756 15_665 ? Na2 Na3 Na1 108(4) . 15_665 ? Na3 Na3 Na2 68(10) 6_654 6_654 ? Na1 Na3 Na2 95(5) . 6_654 ? Na3 Na3 Na2 92(6) 12_756 6_654 ? Na3 Na3 Na2 125(7) 15_665 6_654 ? Na1 Na3 Na2 22(3) 6_654 6_654 ? Na1 Na3 Na2 112(4) 12_756 6_654 ? Na2 Na3 Na2 114(3) . 6_654 ? Na1 Na3 Na2 113(4) 15_665 6_654 ? Na3 Na3 Na2 122(3) 6_654 12_756 ? Na1 Na3 Na2 139(7) . 12_756 ? Na3 Na3 Na2 53(6) 12_756 12_756 ? Na3 Na3 Na2 61(5) 15_665 12_756 ? Na1 Na3 Na2 139(6) 6_654 12_756 ? Na1 Na3 Na2 24(2) 12_756 12_756 ? Na2 Na3 Na2 125(4) . 12_756 ? Na1 Na3 Na2 65.5(19) 15_665 12_756 ? Na2 Na3 Na2 118(4) 6_654 12_756 ? Na3 Na3 Na2 45(3) 6_654 15_665 ? Na1 Na3 Na2 117(6) . 15_665 ? Na3 Na3 Na2 37(5) 12_756 15_665 ? Na3 Na3 Na2 26(5) 15_665 15_665 ? Na1 Na3 Na2 95(3) 6_654 15_665 ? Na1 Na3 Na2 57(2) 12_756 15_665 ? Na2 Na3 Na2 106(3) . 15_665 ? Na1 Na3 Na2 15.5(16) 15_665 15_665 ? Na2 Na3 Na2 102(3) 6_654 15_665 ? Na2 Na3 Na2 80(2) 12_756 15_665 ? 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 O61 Eu N11 C20 84.5(5) . . . . ? O13 Eu N11 C20 -177.4(5) . . . . ? O26 Eu N11 C20 12.0(5) . . . . ? O42 Eu N11 C20 -131.0(5) . . . . ? O43 Eu N11 C20 -90.2(6) . . . . ? O32 Eu N11 C20 -94.1(5) . . . . ? O52 Eu N11 C20 145.9(5) . . . . ? N22 Eu N11 C20 2.3(5) . . . . ? O33 Eu N11 C20 -65.0(5) . . . . ? O53 Eu N11 C20 94.8(5) 6_554 . . . ? N41 Eu N11 C20 -117.6(5) . . . . ? O61 Eu N11 C12 -95.6(4) . . . . ? O13 Eu N11 C12 2.5(4) . . . . ? O26 Eu N11 C12 -168.2(4) . . . . ? O42 Eu N11 C12 48.8(4) . . . . ? O43 Eu N11 C12 89.6(6) . . . . ? O32 Eu N11 C12 85.7(4) . . . . ? O52 Eu N11 C12 -34.3(4) . . . . ? N22 Eu N11 C12 -177.9(5) . . . . ? O33 Eu N11 C12 114.8(4) . . . . ? O53 Eu N11 C12 -85.4(4) 6_554 . . . ? N41 Eu N11 C12 62.3(5) . . . . ? C20 N11 C12 C13 177.2(6) . . . . ? Eu N11 C12 C13 -2.6(7) . . . . ? C20 N11 C12 C17 0.0(9) . . . . ? Eu N11 C12 C17 -179.9(5) . . . . ? N11 C12 C13 O13 0.7(8) . . . . ? C17 C12 C13 O13 178.0(6) . . . . ? N11 C12 C13 C14 -180.0(6) . . . . ? C17 C12 C13 C14 -2.6(9) . . . . ? C14 C13 O13 Eu -177.3(5) . . . . ? C12 C13 O13 Eu 2.0(7) . . . . ? O61 Eu O13 C13 66.6(4) . . . . ? O26 Eu O13 C13 75.4(9) . . . . ? O42 Eu O13 C13 -140.6(4) . . . . ? O43 Eu O13 C13 -160.8(4) . . . . ? O32 Eu O13 C13 -68.3(4) . . . . ? O52 Eu O13 C13 141.1(4) . . . . ? N11 Eu O13 C13 -2.3(4) . . . . ? N22 Eu O13 C13 -2.7(5) . . . . ? O33 Eu O13 C13 -86.8(4) . . . . ? O53 Eu O13 C13 130.7(4) 6_554 . . . ? N41 Eu O13 C13 -149.1(4) . . . . ? O13 C13 C14 C15 -178.7(7) . . . . ? C12 C13 C14 C15 2.0(11) . . . . ? C13 C14 C15 C16 -1.8(15) . . . . ? C14 C15 C16 C17 2.1(16) . . . . ? C15 C16 C17 C12 -2.6(14) . . . . ? C15 C16 C17 C18 180.0(9) . . . . ? N11 C12 C17 C16 -179.9(7) . . . . ? C13 C12 C17 C16 2.9(11) . . . . ? N11 C12 C17 C18 -2.3(10) . . . . ? C13 C12 C17 C18 -179.5(6) . . . . ? C16 C17 C18 C19 -179.1(9) . . . . ? C12 C17 C18 C19 3.4(11) . . . . ? C17 C18 C19 C20 -2.3(12) . . . . ? C12 N11 C20 C19 1.4(9) . . . . ? Eu N11 C20 C19 -178.7(5) . . . . ? C12 N11 C20 C21 178.8(5) . . . . ? Eu N11 C20 C21 -1.4(8) . . . . ? C18 C19 C20 N11 -0.3(11) . . . . ? C18 C19 C20 C21 -177.5(7) . . . . ? N11 C20 C21 N22 -1.8(9) . . . . ? C19 C20 C21 N22 175.6(7) . . . . ? C20 C21 N22 N23 -177.5(6) . . . . ? C20 C21 N22 Eu 4.2(9) . . . . ? O61 Eu N22 C21 -80.1(5) . . . . ? O13 Eu N22 C21 -3.0(6) . . . . ? O26 Eu N22 C21 -173.3(6) . . . . ? O42 Eu N22 C21 94.5(5) . . . . ? O43 Eu N22 C21 154.1(5) . . . . ? O32 Eu N22 C21 57.9(5) . . . . ? O52 Eu N22 C21 -91.5(6) . . . . ? N11 Eu N22 C21 -3.4(5) . . . . ? O33 Eu N22 C21 104.5(5) . . . . ? O53 Eu N22 C21 -134.3(5) 6_554 . . . ? N41 Eu N22 C21 128.6(5) . . . . ? O61 Eu N22 N23 101.5(4) . . . . ? O13 Eu N22 N23 178.7(4) . . . . ? O26 Eu N22 N23 8.4(4) . . . . ? O42 Eu N22 N23 -83.9(5) . . . . ? O43 Eu N22 N23 -24.2(5) . . . . ? O32 Eu N22 N23 -120.4(4) . . . . ? O52 Eu N22 N23 90.1(5) . . . . ? N11 Eu N22 N23 178.3(5) . . . . ? O33 Eu N22 N23 -73.9(4) . . . . ? O53 Eu N22 N23 47.3(5) 6_554 . . . ? N41 Eu N22 N23 -49.8(5) . . . . ? C21 N22 N23 C24 171.4(6) . . . . ? Eu N22 N23 C24 -10.2(7) . . . . ? N22 N23 C24 O26 4.6(10) . . . . ? N22 N23 C24 N25 -175.1(6) . . . . ? N25 C24 O26 Eu -175.8(5) . . . . ? N23 C24 O26 Eu 4.5(9) . . . . ? O61 Eu O26 C24 -81.0(5) . . . . ? O13 Eu O26 C24 -89.8(9) . . . . ? O42 Eu O26 C24 128.2(5) . . . . ? O43 Eu O26 C24 143.3(6) . . . . ? O32 Eu O26 C24 51.8(6) . . . . ? O52 Eu O26 C24 -152.2(5) . . . . ? N11 Eu O26 C24 -16.4(6) . . . . ? N22 Eu O26 C24 -6.8(5) . . . . ? O33 Eu O26 C24 73.3(5) . . . . ? O53 Eu O26 C24 -147.9(6) 6_554 . . . ? N41 Eu O26 C24 134.4(5) . . . . ? O61 Eu N31 O33 107.2(5) . . . . ? O13 Eu N31 O33 -164.4(4) . . . . ? O26 Eu N31 O33 19.1(5) . . . . ? O42 Eu N31 O33 -95.3(5) . . . . ? O43 Eu N31 O33 -48.0(4) . . . . ? O32 Eu N31 O33 166.5(7) . . . . ? O52 Eu N31 O33 -107.5(5) . . . . ? N11 Eu N31 O33 135.5(5) . . . . ? N22 Eu N31 O33 76.4(4) . . . . ? O53 Eu N31 O33 -38.3(6) 6_554 . . . ? N41 Eu N31 O33 -69.1(4) . . . . ? O61 Eu N31 O34 -113(2) . . . . ? O13 Eu N31 O34 -24(2) . . . . ? O26 Eu N31 O34 159(2) . . . . ? O42 Eu N31 O34 45(2) . . . . ? O43 Eu N31 O34 92(2) . . . . ? O32 Eu N31 O34 -53(2) . . . . ? O52 Eu N31 O34 33(2) . . . . ? N11 Eu N31 O34 -84(2) . . . . ? N22 Eu N31 O34 -144(2) . . . . ? O33 Eu N31 O34 140(2) . . . . ? O53 Eu N31 O34 102(2) 6_554 . . . ? N41 Eu N31 O34 71(2) . . . . ? O61 Eu N31 O32 -59.3(6) . . . . ? O13 Eu N31 O32 29.1(4) . . . . ? O26 Eu N31 O32 -147.5(4) . . . . ? O42 Eu N31 O32 98.1(4) . . . . ? O43 Eu N31 O32 145.5(4) . . . . ? O52 Eu N31 O32 85.9(4) . . . . ? N11 Eu N31 O32 -31.0(4) . . . . ? N22 Eu N31 O32 -90.1(4) . . . . ? O33 Eu N31 O32 -166.5(7) . . . . ? O53 Eu N31 O32 155.2(4) 6_554 . . . ? N41 Eu N31 O32 124.3(4) . . . . ? O33 N31 O32 Eu -14.1(7) . . . . ? O34 N31 O32 Eu 167.5(5) . . . . ? O61 Eu O32 N31 142.5(4) . . . . ? O13 Eu O32 N31 -149.0(4) . . . . ? O26 Eu O32 N31 36.6(5) . . . . ? O42 Eu O32 N31 -70.5(4) . . . . ? O43 Eu O32 N31 -34.6(4) . . . . ? O52 Eu O32 N31 -115.0(4) . . . . ? N11 Eu O32 N31 144.1(5) . . . . ? N22 Eu O32 N31 85.0(4) . . . . ? O33 Eu O32 N31 6.8(4) . . . . ? O53 Eu O32 N31 -56.2(7) 6_554 . . . ? N41 Eu O32 N31 -50.5(4) . . . . ? O34 N31 O33 Eu -168.4(7) . . . . ? O32 N31 O33 Eu 13.4(7) . . . . ? O61 Eu O33 N31 -106.8(5) . . . . ? O13 Eu O33 N31 16.9(5) . . . . ? O26 Eu O33 N31 -160.4(5) . . . . ? O42 Eu O33 N31 74.4(4) . . . . ? O43 Eu O33 N31 127.1(5) . . . . ? O32 Eu O33 N31 -7.9(4) . . . . ? O52 Eu O33 N31 93.8(5) . . . . ? N11 Eu O33 N31 -44.1(4) . . . . ? N22 Eu O33 N31 -98.5(5) . . . . ? O53 Eu O33 N31 152.7(4) 6_554 . . . ? N41 Eu O33 N31 101.3(5) . . . . ? O61 Eu N41 O43 -59.6(5) . . . . ? O13 Eu N41 O43 -152.9(4) . . . . ? O26 Eu N41 O43 21.2(4) . . . . ? O42 Eu N41 O43 -172.7(6) . . . . ? O32 Eu N41 O43 137.4(4) . . . . ? O52 Eu N41 O43 -90.8(4) . . . . ? N11 Eu N41 O43 157.8(4) . . . . ? N22 Eu N41 O43 68.2(4) . . . . ? O33 Eu N41 O43 94.6(4) . . . . ? O53 Eu N41 O43 -44.3(4) 6_554 . . . ? O61 Eu N41 O44 -150(4) . . . . ? O13 Eu N41 O44 117(4) . . . . ? O26 Eu N41 O44 -69(4) . . . . ? O42 Eu N41 O44 97(4) . . . . ? O43 Eu N41 O44 -90(4) . . . . ? O32 Eu N41 O44 48(4) . . . . ? O52 Eu N41 O44 179(100) . . . . ? N11 Eu N41 O44 68(4) . . . . ? N22 Eu N41 O44 -22(4) . . . . ? O33 Eu N41 O44 5(4) . . . . ? O53 Eu N41 O44 -134(4) 6_554 . . . ? O61 Eu N41 O42 113.1(4) . . . . ? O13 Eu N41 O42 19.8(4) . . . . ? O26 Eu N41 O42 -166.1(4) . . . . ? O43 Eu N41 O42 172.7(6) . . . . ? O32 Eu N41 O42 -49.9(4) . . . . ? O52 Eu N41 O42 81.9(4) . . . . ? N11 Eu N41 O42 -29.5(5) . . . . ? N22 Eu N41 O42 -119.1(3) . . . . ? O33 Eu N41 O42 -92.7(4) . . . . ? O53 Eu N41 O42 128.4(4) 6_554 . . . ? O43 N41 O42 Eu 7.3(6) . . . . ? O44 N41 O42 Eu -172.7(6) . . . . ? O61 Eu O42 N41 -103.4(4) . . . . ? O13 Eu O42 N41 -159.3(4) . . . . ? O26 Eu O42 N41 15.3(4) . . . . ? O43 Eu O42 N41 -3.9(3) . . . . ? O32 Eu O42 N41 125.1(4) . . . . ? O52 Eu O42 N41 -90.7(4) . . . . ? N11 Eu O42 N41 159.2(3) . . . . ? N22 Eu O42 N41 85.9(4) . . . . ? O33 Eu O42 N41 75.4(4) . . . . ? O53 Eu O42 N41 -50.5(4) 6_554 . . . ? O44 N41 O43 Eu 172.8(6) . . . . ? O42 N41 O43 Eu -7.2(6) . . . . ? O61 Eu O43 N41 139.8(4) . . . . ? O13 Eu O43 N41 30.5(4) . . . . ? O26 Eu O43 N41 -157.1(4) . . . . ? O42 Eu O43 N41 4.1(3) . . . . ? O32 Eu O43 N41 -43.1(4) . . . . ? O52 Eu O43 N41 82.9(4) . . . . ? N11 Eu O43 N41 -46.6(6) . . . . ? N22 Eu O43 N41 -127.3(4) . . . . ? O33 Eu O43 N41 -74.1(4) . . . . ? O53 Eu O43 N41 129.6(4) 6_554 . . . ? O53 N51 O52 Eu -1.9(3) 6_554 . . . ? O53 N51 O52 Eu 178.1(3) . . . . ? O53 N51 O52 Eu 178.1(3) 6_554 . . 6_554 ? O53 N51 O52 Eu -1.9(3) . . . 6_554 ? O61 Eu O52 N51 -71.06(12) . . . . ? O13 Eu O52 N51 -165.20(9) . . . . ? O26 Eu O52 N51 6.47(10) . . . . ? O42 Eu O52 N51 116.18(10) . . . . ? O43 Eu O52 N51 66.41(10) . . . . ? O32 Eu O52 N51 159.18(13) . . . . ? N11 Eu O52 N51 -129.95(11) . . . . ? N22 Eu O52 N51 -59.7(2) . . . . ? O33 Eu O52 N51 97.6(2) . . . . ? O53 Eu O52 N51 0.98(15) 6_554 . . . ? N41 Eu O52 N51 90.72(11) . . . . ? O61 Eu O52 Eu 108.94(12) . . . 6_554 ? O13 Eu O52 Eu 14.80(9) . . . 6_554 ? O26 Eu O52 Eu -173.53(10) . . . 6_554 ? O42 Eu O52 Eu -63.82(10) . . . 6_554 ? O43 Eu O52 Eu -113.59(10) . . . 6_554 ? O32 Eu O52 Eu -20.82(13) . . . 6_554 ? N11 Eu O52 Eu 50.05(11) . . . 6_554 ? N22 Eu O52 Eu 120.3(2) . . . 6_554 ? O33 Eu O52 Eu -82.4(2) . . . 6_554 ? O53 Eu O52 Eu -179.02(15) 6_554 . . 6_554 ? N41 Eu O52 Eu -89.28(11) . . . 6_554 ? O53 N51 O53 Eu -178.3(2) 6_554 . . 6_554 ? O52 N51 O53 Eu 1.7(2) . . . 6_554 ? O13 Eu O61 C62 78.9(14) . . . . ? O26 Eu O61 C62 -99.8(14) . . . . ? O42 Eu O61 C62 26.6(16) . . . . ? O43 Eu O61 C62 -43.3(15) . . . . ? O32 Eu O61 C62 140.4(14) . . . . ? O52 Eu O61 C62 14.0(14) . . . . ? N11 Eu O61 C62 138.9(15) . . . . ? N22 Eu O61 C62 -159.7(15) . . . . ? O33 Eu O61 C62 -151.4(14) . . . . ? O53 Eu O61 C62 -33.4(14) 6_554 . . . ? N41 Eu O61 C62 -17.1(15) . . . . ? Eu O61 C62 N63 -165.8(8) . . . . ? O61 C62 N63 C64 167.3(11) . . . . ? O61 C62 N63 C65 -15.9(16) . . . . ? Na3 Na1 Na2 Na3 52(11) 6_654 . . . ? Na1 Na1 Na2 Na3 117(17) 6_654 . . . ? Na3 Na1 Na2 Na3 15(9) 15_665 . . . ? Na3 Na1 Na2 Na3 15(9) 12_756 . . . ? Na2 Na1 Na2 Na3 142(18) 6_654 . . . ? Na1 Na1 Na2 Na3 25(10) 15_665 . . . ? Na1 Na1 Na2 Na3 -6(8) 12_756 . . . ? Na2 Na1 Na2 Na3 -26(9) 12_756 . . . ? Na2 Na1 Na2 Na3 39(10) 15_665 . . . ? Na3 Na1 Na2 Na3 -52(11) . . . 6_654 ? Na1 Na1 Na2 Na3 65(9) 6_654 . . 6_654 ? Na3 Na1 Na2 Na3 -37(6) 15_665 . . 6_654 ? Na3 Na1 Na2 Na3 -37(6) 12_756 . . 6_654 ? Na2 Na1 Na2 Na3 90(10) 6_654 . . 6_654 ? Na1 Na1 Na2 Na3 -27(4) 15_665 . . 6_654 ? Na1 Na1 Na2 Na3 -57(6) 12_756 . . 6_654 ? Na2 Na1 Na2 Na3 -78(6) 12_756 . . 6_654 ? Na2 Na1 Na2 Na3 -12(5) 15_665 . . 6_654 ? Na3 Na1 Na2 Na3 -15(9) . . . 15_665 ? Na3 Na1 Na2 Na3 37(6) 6_654 . . 15_665 ? Na1 Na1 Na2 Na3 102(10) 6_654 . . 15_665 ? Na3 Na1 Na2 Na3 0(7) 12_756 . . 15_665 ? Na2 Na1 Na2 Na3 128(11) 6_654 . . 15_665 ? Na1 Na1 Na2 Na3 10(3) 15_665 . . 15_665 ? Na1 Na1 Na2 Na3 -20(3) 12_756 . . 15_665 ? Na2 Na1 Na2 Na3 -41(3) 12_756 . . 15_665 ? Na2 Na1 Na2 Na3 25(3) 15_665 . . 15_665 ? Na3 Na1 Na2 Na1 -117(17) . . . 6_654 ? Na3 Na1 Na2 Na1 -65(9) 6_654 . . 6_654 ? Na3 Na1 Na2 Na1 -102(10) 15_665 . . 6_654 ? Na3 Na1 Na2 Na1 -102(11) 12_756 . . 6_654 ? Na2 Na1 Na2 Na1 26(2) 6_654 . . 6_654 ? Na1 Na1 Na2 Na1 -92(8) 15_665 . . 6_654 ? Na1 Na1 Na2 Na1 -122(11) 12_756 . . 6_654 ? Na2 Na1 Na2 Na1 -143(10) 12_756 . . 6_654 ? Na2 Na1 Na2 Na1 -77(8) 15_665 . . 6_654 ? Na3 Na1 Na2 Na3 -15(9) . . . 12_756 ? Na3 Na1 Na2 Na3 37(6) 6_654 . . 12_756 ? Na1 Na1 Na2 Na3 102(11) 6_654 . . 12_756 ? Na3 Na1 Na2 Na3 0(7) 15_665 . . 12_756 ? Na2 Na1 Na2 Na3 127(13) 6_654 . . 12_756 ? Na1 Na1 Na2 Na3 9(5) 15_665 . . 12_756 ? Na1 Na1 Na2 Na3 -21(5) 12_756 . . 12_756 ? Na2 Na1 Na2 Na3 -41(6) 12_756 . . 12_756 ? Na2 Na1 Na2 Na3 24(5) 15_665 . . 12_756 ? Na3 Na1 Na2 Na1 -25(10) . . . 15_665 ? Na3 Na1 Na2 Na1 27(4) 6_654 . . 15_665 ? Na1 Na1 Na2 Na1 92(8) 6_654 . . 15_665 ? Na3 Na1 Na2 Na1 -10(3) 15_665 . . 15_665 ? Na3 Na1 Na2 Na1 -9(5) 12_756 . . 15_665 ? Na2 Na1 Na2 Na1 118(10) 6_654 . . 15_665 ? Na1 Na1 Na2 Na1 -30(3) 12_756 . . 15_665 ? Na2 Na1 Na2 Na1 -51(3) 12_756 . . 15_665 ? Na2 Na1 Na2 Na1 15.0(11) 15_665 . . 15_665 ? Na3 Na1 Na2 Na2 -142(18) . . . 6_654 ? Na3 Na1 Na2 Na2 -90(10) 6_654 . . 6_654 ? Na1 Na1 Na2 Na2 -26(2) 6_654 . . 6_654 ? Na3 Na1 Na2 Na2 -128(11) 15_665 . . 6_654 ? Na3 Na1 Na2 Na2 -127(13) 12_756 . . 6_654 ? Na1 Na1 Na2 Na2 -118(10) 15_665 . . 6_654 ? Na1 Na1 Na2 Na2 -148(12) 12_756 . . 6_654 ? Na2 Na1 Na2 Na2 -169(12) 12_756 . . 6_654 ? Na2 Na1 Na2 Na2 -103(10) 15_665 . . 6_654 ? Na3 Na1 Na2 Na1 6(8) . . . 12_756 ? Na3 Na1 Na2 Na1 57(6) 6_654 . . 12_756 ? Na1 Na1 Na2 Na1 122(11) 6_654 . . 12_756 ? Na3 Na1 Na2 Na1 20(3) 15_665 . . 12_756 ? Na3 Na1 Na2 Na1 21(5) 12_756 . . 12_756 ? Na2 Na1 Na2 Na1 148(12) 6_654 . . 12_756 ? Na1 Na1 Na2 Na1 30(3) 15_665 . . 12_756 ? Na2 Na1 Na2 Na1 -20.8(15) 12_756 . . 12_756 ? Na2 Na1 Na2 Na1 45(3) 15_665 . . 12_756 ? Na2 Na1 Na3 Na3 93(16) . . . 6_654 ? Na1 Na1 Na3 Na3 -53(9) 6_654 . . 6_654 ? Na3 Na1 Na3 Na3 67(6) 15_665 . . 6_654 ? Na3 Na1 Na3 Na3 39(20) 12_756 . . 6_654 ? Na2 Na1 Na3 Na3 -68(10) 6_654 . . 6_654 ? Na1 Na1 Na3 Na3 54(9) 15_665 . . 6_654 ? Na1 Na1 Na3 Na3 109(19) 12_756 . . 6_654 ? Na2 Na1 Na3 Na3 145(18) 12_756 . . 6_654 ? Na2 Na1 Na3 Na3 38(8) 15_665 . . 6_654 ? Na2 Na1 Na3 Na3 54(28) . . . 12_756 ? Na3 Na1 Na3 Na3 -39(20) 6_654 . . 12_756 ? Na1 Na1 Na3 Na3 -92(21) 6_654 . . 12_756 ? Na3 Na1 Na3 Na3 28(14) 15_665 . . 12_756 ? Na2 Na1 Na3 Na3 -107(22) 6_654 . . 12_756 ? Na1 Na1 Na3 Na3 15(16) 15_665 . . 12_756 ? Na1 Na1 Na3 Na3 70(15) 12_756 . . 12_756 ? Na2 Na1 Na3 Na3 106(23) 12_756 . . 12_756 ? Na2 Na1 Na3 Na3 -1(17) 15_665 . . 12_756 ? Na2 Na1 Na3 Na3 26(17) . . . 15_665 ? Na3 Na1 Na3 Na3 -67(6) 6_654 . . 15_665 ? Na1 Na1 Na3 Na3 -120(8) 6_654 . . 15_665 ? Na3 Na1 Na3 Na3 -28(14) 12_756 . . 15_665 ? Na2 Na1 Na3 Na3 -135(10) 6_654 . . 15_665 ? Na1 Na1 Na3 Na3 -13(5) 15_665 . . 15_665 ? Na1 Na1 Na3 Na3 41(14) 12_756 . . 15_665 ? Na2 Na1 Na3 Na3 78(15) 12_756 . . 15_665 ? Na2 Na1 Na3 Na3 -29(5) 15_665 . . 15_665 ? Na2 Na1 Na3 Na1 146(12) . . . 6_654 ? Na3 Na1 Na3 Na1 53(9) 6_654 . . 6_654 ? Na3 Na1 Na3 Na1 120(8) 15_665 . . 6_654 ? Na3 Na1 Na3 Na1 92(21) 12_756 . . 6_654 ? Na2 Na1 Na3 Na1 -15(3) 6_654 . . 6_654 ? Na1 Na1 Na3 Na1 107(6) 15_665 . . 6_654 ? Na1 Na1 Na3 Na1 162(15) 12_756 . . 6_654 ? Na2 Na1 Na3 Na1 -162(10) 12_756 . . 6_654 ? Na2 Na1 Na3 Na1 91(5) 15_665 . . 6_654 ? Na2 Na1 Na3 Na1 -15(23) . . . 12_756 ? Na3 Na1 Na3 Na1 -109(19) 6_654 . . 12_756 ? Na1 Na1 Na3 Na1 -162(15) 6_654 . . 12_756 ? Na3 Na1 Na3 Na1 -41(14) 15_665 . . 12_756 ? Na3 Na1 Na3 Na1 -70(15) 12_756 . . 12_756 ? Na2 Na1 Na3 Na1 -177(15) 6_654 . . 12_756 ? Na1 Na1 Na3 Na1 -55(11) 15_665 . . 12_756 ? Na2 Na1 Na3 Na1 36(10) 12_756 . . 12_756 ? Na2 Na1 Na3 Na1 -71(12) 15_665 . . 12_756 ? Na3 Na1 Na3 Na2 -93(16) 6_654 . . . ? Na1 Na1 Na3 Na2 -146(12) 6_654 . . . ? Na3 Na1 Na3 Na2 -26(17) 15_665 . . . ? Na3 Na1 Na3 Na2 -54(28) 12_756 . . . ? Na2 Na1 Na3 Na2 -162(9) 6_654 . . . ? Na1 Na1 Na3 Na2 -39(15) 15_665 . . . ? Na1 Na1 Na3 Na2 15(23) 12_756 . . . ? Na2 Na1 Na3 Na2 51(15) 12_756 . . . ? Na2 Na1 Na3 Na2 -56(13) 15_665 . . . ? Na2 Na1 Na3 Na1 39(15) . . . 15_665 ? Na3 Na1 Na3 Na1 -54(9) 6_654 . . 15_665 ? Na1 Na1 Na3 Na1 -107(6) 6_654 . . 15_665 ? Na3 Na1 Na3 Na1 13(5) 15_665 . . 15_665 ? Na3 Na1 Na3 Na1 -15(16) 12_756 . . 15_665 ? Na2 Na1 Na3 Na1 -122(7) 6_654 . . 15_665 ? Na1 Na1 Na3 Na1 55(11) 12_756 . . 15_665 ? Na2 Na1 Na3 Na1 91(10) 12_756 . . 15_665 ? Na2 Na1 Na3 Na1 -16(3) 15_665 . . 15_665 ? Na2 Na1 Na3 Na2 162(9) . . . 6_654 ? Na3 Na1 Na3 Na2 68(10) 6_654 . . 6_654 ? Na1 Na1 Na3 Na2 15(3) 6_654 . . 6_654 ? Na3 Na1 Na3 Na2 135(10) 15_665 . . 6_654 ? Na3 Na1 Na3 Na2 107(22) 12_756 . . 6_654 ? Na1 Na1 Na3 Na2 122(7) 15_665 . . 6_654 ? Na1 Na1 Na3 Na2 177(15) 12_756 . . 6_654 ? Na2 Na1 Na3 Na2 -147(9) 12_756 . . 6_654 ? Na2 Na1 Na3 Na2 106(5) 15_665 . . 6_654 ? Na2 Na1 Na3 Na2 -51(15) . . . 12_756 ? Na3 Na1 Na3 Na2 -145(18) 6_654 . . 12_756 ? Na1 Na1 Na3 Na2 162(10) 6_654 . . 12_756 ? Na3 Na1 Na3 Na2 -78(15) 15_665 . . 12_756 ? Na3 Na1 Na3 Na2 -106(23) 12_756 . . 12_756 ? Na2 Na1 Na3 Na2 147(9) 6_654 . . 12_756 ? Na1 Na1 Na3 Na2 -91(10) 15_665 . . 12_756 ? Na1 Na1 Na3 Na2 -36(10) 12_756 . . 12_756 ? Na2 Na1 Na3 Na2 -107(11) 15_665 . . 12_756 ? Na2 Na1 Na3 Na2 56(13) . . . 15_665 ? Na3 Na1 Na3 Na2 -38(8) 6_654 . . 15_665 ? Na1 Na1 Na3 Na2 -91(5) 6_654 . . 15_665 ? Na3 Na1 Na3 Na2 29(5) 15_665 . . 15_665 ? Na3 Na1 Na3 Na2 1(17) 12_756 . . 15_665 ? Na2 Na1 Na3 Na2 -106(5) 6_654 . . 15_665 ? Na1 Na1 Na3 Na2 16(3) 15_665 . . 15_665 ? Na1 Na1 Na3 Na2 71(12) 12_756 . . 15_665 ? Na2 Na1 Na3 Na2 107(11) 12_756 . . 15_665 ? Na1 Na2 Na3 Na3 -87(14) . . . 6_654 ? Na3 Na2 Na3 Na3 70(4) 15_665 . . 6_654 ? Na1 Na2 Na3 Na3 -54(6) 6_654 . . 6_654 ? Na3 Na2 Na3 Na3 60(15) 12_756 . . 6_654 ? Na1 Na2 Na3 Na3 60(7) 15_665 . . 6_654 ? Na2 Na2 Na3 Na3 -67(7) 6_654 . . 6_654 ? Na1 Na2 Na3 Na3 103(10) 12_756 . . 6_654 ? Na3 Na2 Na3 Na1 87(14) 6_654 . . . ? Na3 Na2 Na3 Na1 157(15) 15_665 . . . ? Na1 Na2 Na3 Na1 33(12) 6_654 . . . ? Na3 Na2 Na3 Na1 147(19) 12_756 . . . ? Na1 Na2 Na3 Na1 146(13) 15_665 . . . ? Na2 Na2 Na3 Na1 20(10) 6_654 . . . ? Na1 Na2 Na3 Na1 -170(14) 12_756 . . . ? Na1 Na2 Na3 Na3 -147(19) . . . 12_756 ? Na3 Na2 Na3 Na3 -60(15) 6_654 . . 12_756 ? Na3 Na2 Na3 Na3 10(11) 15_665 . . 12_756 ? Na1 Na2 Na3 Na3 -113(13) 6_654 . . 12_756 ? Na1 Na2 Na3 Na3 0(9) 15_665 . . 12_756 ? Na2 Na2 Na3 Na3 -127(12) 6_654 . . 12_756 ? Na1 Na2 Na3 Na3 43(7) 12_756 . . 12_756 ? Na1 Na2 Na3 Na3 -157(15) . . . 15_665 ? Na3 Na2 Na3 Na3 -70(4) 6_654 . . 15_665 ? Na1 Na2 Na3 Na3 -124(6) 6_654 . . 15_665 ? Na3 Na2 Na3 Na3 -10(11) 12_756 . . 15_665 ? Na1 Na2 Na3 Na3 -10(5) 15_665 . . 15_665 ? Na2 Na2 Na3 Na3 -137(7) 6_654 . . 15_665 ? Na1 Na2 Na3 Na3 33(7) 12_756 . . 15_665 ? Na1 Na2 Na3 Na1 -33(12) . . . 6_654 ? Na3 Na2 Na3 Na1 54(6) 6_654 . . 6_654 ? Na3 Na2 Na3 Na1 124(6) 15_665 . . 6_654 ? Na3 Na2 Na3 Na1 113(13) 12_756 . . 6_654 ? Na1 Na2 Na3 Na1 113(5) 15_665 . . 6_654 ? Na2 Na2 Na3 Na1 -13(3) 6_654 . . 6_654 ? Na1 Na2 Na3 Na1 156(8) 12_756 . . 6_654 ? Na1 Na2 Na3 Na1 170(14) . . . 12_756 ? Na3 Na2 Na3 Na1 -103(10) 6_654 . . 12_756 ? Na3 Na2 Na3 Na1 -33(7) 15_665 . . 12_756 ? Na1 Na2 Na3 Na1 -156(8) 6_654 . . 12_756 ? Na3 Na2 Na3 Na1 -43(7) 12_756 . . 12_756 ? Na1 Na2 Na3 Na1 -43(4) 15_665 . . 12_756 ? Na2 Na2 Na3 Na1 -170(7) 6_654 . . 12_756 ? Na1 Na2 Na3 Na1 -146(13) . . . 15_665 ? Na3 Na2 Na3 Na1 -60(7) 6_654 . . 15_665 ? Na3 Na2 Na3 Na1 10(5) 15_665 . . 15_665 ? Na1 Na2 Na3 Na1 -113(5) 6_654 . . 15_665 ? Na3 Na2 Na3 Na1 0(9) 12_756 . . 15_665 ? Na2 Na2 Na3 Na1 -126(5) 6_654 . . 15_665 ? Na1 Na2 Na3 Na1 43(4) 12_756 . . 15_665 ? Na1 Na2 Na3 Na2 -20(10) . . . 6_654 ? Na3 Na2 Na3 Na2 67(7) 6_654 . . 6_654 ? Na3 Na2 Na3 Na2 137(7) 15_665 . . 6_654 ? Na1 Na2 Na3 Na2 13(3) 6_654 . . 6_654 ? Na3 Na2 Na3 Na2 127(12) 12_756 . . 6_654 ? Na1 Na2 Na3 Na2 126(5) 15_665 . . 6_654 ? Na1 Na2 Na3 Na2 170(7) 12_756 . . 6_654 ? Na1 Na2 Na3 Na2 141(12) . . . 12_756 ? Na3 Na2 Na3 Na2 -132(10) 6_654 . . 12_756 ? Na3 Na2 Na3 Na2 -62(8) 15_665 . . 12_756 ? Na1 Na2 Na3 Na2 174(6) 6_654 . . 12_756 ? Na3 Na2 Na3 Na2 -72(9) 12_756 . . 12_756 ? Na1 Na2 Na3 Na2 -73(3) 15_665 . . 12_756 ? Na2 Na2 Na3 Na2 161(5) 6_654 . . 12_756 ? Na1 Na2 Na3 Na2 -29(3) 12_756 . . 12_756 ? Na1 Na2 Na3 Na2 -130(12) . . . 15_665 ? Na3 Na2 Na3 Na2 -44(7) 6_654 . . 15_665 ? Na3 Na2 Na3 Na2 26(5) 15_665 . . 15_665 ? Na1 Na2 Na3 Na2 -97(4) 6_654 . . 15_665 ? Na3 Na2 Na3 Na2 16(9) 12_756 . . 15_665 ? Na1 Na2 Na3 Na2 16.0(18) 15_665 . . 15_665 ? Na2 Na2 Na3 Na2 -110(4) 6_654 . . 15_665 ? Na1 Na2 Na3 Na2 59(4) 12_756 . . 15_665 ? _diffrn_measured_fraction_theta_max 0.999 _diffrn_reflns_theta_full 27.86 _diffrn_measured_fraction_theta_full 0.999 _refine_diff_density_max 0.614 _refine_diff_density_min -0.785 _refine_diff_density_rms 0.127 data_fro3131 _database_code_depnum_ccdc_archive 'CCDC 273596' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C12 H15 Cl N4 O3' _chemical_formula_weight 298.73 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' Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting triclinic _symmetry_space_group_name_H-M P-1 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 6.625(1) _cell_length_b 8.080(1) _cell_length_c 12.955(1) _cell_angle_alpha 92.16(1) _cell_angle_beta 91.99(1) _cell_angle_gamma 103.48(1) _cell_volume 673.22(14) _cell_formula_units_Z 2 _cell_measurement_temperature 198(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description needle _exptl_crystal_colour yellow _exptl_crystal_size_max 0.50 _exptl_crystal_size_mid 0.15 _exptl_crystal_size_min 0.03 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.474 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 312 _exptl_absorpt_coefficient_mu 0.297 _exptl_absorpt_correction_type empirical _exptl_absorpt_correction_T_min 0.8655 _exptl_absorpt_correction_T_max 0.9911 _exptl_absorpt_process_details 'SORTAV (Blessing, 1995 & 1997)' _exptl_special_details ; ? ; _diffrn_ambient_temperature 198(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'rotating anode Nonius FR591' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Nonius KappaCCD' _diffrn_measurement_method '\w and \f scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 7086 _diffrn_reflns_av_R_equivalents 0.075 _diffrn_reflns_av_sigmaI/netI 0.0614 _diffrn_reflns_limit_h_min -8 _diffrn_reflns_limit_h_max 8 _diffrn_reflns_limit_k_min -9 _diffrn_reflns_limit_k_max 10 _diffrn_reflns_limit_l_min -15 _diffrn_reflns_limit_l_max 16 _diffrn_reflns_theta_min 2.60 _diffrn_reflns_theta_max 26.30 _reflns_number_total 2718 _reflns_number_gt 1874 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Collect (Nonius B.V., 1998)' _computing_cell_refinement 'Collect (Nonius B.V., 1998)' _computing_data_reduction 'Denzo-SMN (Otwinowski & Minor, 1997)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'SCHAKAL (Keller, 1997)' _computing_publication_material '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. Poor crystals, needle-shaped and always twinned. ; _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^)+(0.1000P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens 'at N from difmap, other geom' _refine_ls_hydrogen_treatment mixed _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 2718 _refine_ls_number_parameters 198 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.1306 _refine_ls_R_factor_gt 0.1014 _refine_ls_wR_factor_ref 0.2543 _refine_ls_wR_factor_gt 0.2423 _refine_ls_goodness_of_fit_ref 1.602 _refine_ls_restrained_S_all 1.602 _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 N1 N 0.7346(5) 1.4384(4) 0.4775(3) 0.0299(8) Uani 1 1 d . . . H1 H 0.704(7) 1.337(6) 0.440(4) 0.044(13) Uiso 1 1 d . . . C2 C 0.7287(6) 1.4423(5) 0.5838(3) 0.0284(9) Uani 1 1 d . . . C3 C 0.6803(6) 1.2904(5) 0.6365(3) 0.0342(10) Uani 1 1 d . . . O3 O 0.6424(5) 1.1448(4) 0.5767(2) 0.0411(8) Uani 1 1 d . . . H3 H 0.5402 1.0747 0.5985 0.062 Uiso 1 1 calc R . . C4 C 0.6743(6) 1.2996(5) 0.7414(3) 0.0344(10) Uani 1 1 d . . . H4 H 0.6397 1.1971 0.7773 0.041 Uiso 1 1 calc R . . C5 C 0.7176(6) 1.4556(6) 0.7977(4) 0.0410(11) Uani 1 1 d . . . H5 H 0.7150 1.4581 0.8710 0.049 Uiso 1 1 calc R . . C6 C 0.7635(7) 1.6040(6) 0.7477(4) 0.0411(11) Uani 1 1 d . . . H6 H 0.7912 1.7098 0.7863 0.049 Uiso 1 1 calc R . . C7 C 0.7704(6) 1.6021(5) 0.6390(3) 0.0347(10) Uani 1 1 d . . . C8 C 0.8126(6) 1.7512(5) 0.5809(4) 0.0366(10) Uani 1 1 d . . . H8 H 0.8407 1.8601 0.6160 0.044 Uiso 1 1 calc R . . C9 C 0.8134(6) 1.7404(5) 0.4763(4) 0.0353(10) Uani 1 1 d . . . H9 H 0.8396 1.8412 0.4386 0.042 Uiso 1 1 calc R . . C10 C 0.7753(6) 1.5793(5) 0.4231(3) 0.0282(9) Uani 1 1 d . . . C11 C 0.7791(6) 1.5585(5) 0.3129(3) 0.0316(9) Uani 1 1 d . . . H11 H 0.7485 1.4486 0.2792 0.038 Uiso 1 1 calc R . . N12 N 0.8255(5) 1.6947(4) 0.2613(3) 0.0304(8) Uani 1 1 d . . . N13 N 0.8331(5) 1.6715(5) 0.1588(3) 0.0348(8) Uani 1 1 d . . . H13 H 0.815(7) 1.569(7) 0.129(4) 0.050(14) Uiso 1 1 d . . . C14 C 0.9004(6) 1.8093(5) 0.0989(4) 0.0361(10) Uani 1 1 d . . . N15 N 0.9220(7) 1.9637(5) 0.1424(3) 0.0469(10) Uani 1 1 d . . . H15A H 0.870(7) 1.982(6) 0.209(5) 0.056 Uiso 1 1 d . . . H15B H 0.970(7) 2.057(7) 0.094(4) 0.056 Uiso 1 1 d . . . O16 O 0.9366(5) 1.7810(4) 0.0075(2) 0.0439(8) Uani 1 1 d . . . Cl1 Cl 0.33457(18) 0.87993(13) 0.67868(9) 0.0464(4) Uani 1 1 d . . . O21 O 1.2390(5) 1.6407(4) -0.0585(3) 0.0572(10) Uani 1 1 d . . . H21 H 1.1401 1.6813 -0.0393 0.086 Uiso 1 1 calc R . . C22 C 1.4244(8) 1.7654(7) -0.0456(5) 0.0626(15) Uani 1 1 d . . . H22A H 1.4157 1.8425 0.0135 0.094 Uiso 1 1 calc R . . H22B H 1.4476 1.8303 -0.1082 0.094 Uiso 1 1 calc R . . H22C H 1.5399 1.7110 -0.0329 0.094 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 N1 0.0380(18) 0.0300(19) 0.022(2) 0.0009(15) 0.0047(14) 0.0075(14) C2 0.035(2) 0.033(2) 0.017(2) 0.0038(16) 0.0047(16) 0.0067(16) C3 0.037(2) 0.039(2) 0.027(3) 0.0061(19) 0.0053(18) 0.0085(17) O3 0.062(2) 0.0292(15) 0.0304(19) 0.0060(13) 0.0118(14) 0.0048(13) C4 0.046(2) 0.039(2) 0.019(2) 0.0088(18) 0.0064(17) 0.0089(18) C5 0.045(2) 0.053(3) 0.023(3) 0.008(2) 0.0050(18) 0.007(2) C6 0.049(2) 0.044(3) 0.027(3) -0.004(2) 0.0039(19) 0.005(2) C7 0.036(2) 0.041(2) 0.025(3) 0.0010(18) 0.0035(17) 0.0053(17) C8 0.044(2) 0.034(2) 0.030(3) -0.0007(19) 0.0055(19) 0.0062(18) C9 0.042(2) 0.029(2) 0.034(3) 0.0067(18) 0.0041(18) 0.0047(16) C10 0.039(2) 0.0274(19) 0.018(2) 0.0069(16) 0.0060(16) 0.0057(15) C11 0.040(2) 0.029(2) 0.025(2) 0.0002(17) 0.0056(17) 0.0067(16) N12 0.0434(18) 0.0301(17) 0.0186(19) 0.0046(14) 0.0077(14) 0.0092(14) N13 0.053(2) 0.032(2) 0.019(2) 0.0052(15) 0.0075(16) 0.0080(16) C14 0.046(2) 0.038(2) 0.026(3) 0.0071(19) 0.0057(19) 0.0094(18) N15 0.075(3) 0.035(2) 0.030(2) 0.0068(18) 0.016(2) 0.0095(18) O16 0.065(2) 0.0427(17) 0.0263(19) 0.0077(14) 0.0140(14) 0.0143(15) Cl1 0.0731(8) 0.0320(6) 0.0308(7) 0.0002(5) 0.0169(5) 0.0039(5) O21 0.064(2) 0.048(2) 0.059(3) -0.0141(18) 0.0121(18) 0.0121(16) C22 0.063(3) 0.066(4) 0.053(4) -0.002(3) 0.003(3) 0.005(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 N1 C10 1.340(5) . ? N1 C2 1.379(5) . ? C2 C3 1.404(6) . ? C2 C7 1.416(6) . ? C3 O3 1.352(5) . ? C3 C4 1.360(6) . ? C4 C5 1.397(6) . ? C5 C6 1.361(7) . ? C6 C7 1.409(6) . ? C7 C8 1.422(6) . ? C8 C9 1.356(6) . ? C9 C10 1.414(6) . ? C10 C11 1.432(6) . ? C11 N12 1.290(5) . ? N12 N13 1.339(5) . ? N13 C14 1.377(6) . ? C14 O16 1.240(5) . ? C14 N15 1.324(6) . ? O21 C22 1.395(6) . ? 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 C10 N1 C2 123.1(3) . . ? N1 C2 C3 120.6(4) . . ? N1 C2 C7 119.0(4) . . ? C3 C2 C7 120.4(4) . . ? O3 C3 C4 125.3(4) . . ? O3 C3 C2 115.8(4) . . ? C4 C3 C2 118.8(4) . . ? C3 C4 C5 121.8(4) . . ? C6 C5 C4 120.1(4) . . ? C5 C6 C7 120.5(4) . . ? C6 C7 C2 118.3(4) . . ? C6 C7 C8 124.0(4) . . ? C2 C7 C8 117.7(4) . . ? C9 C8 C7 121.0(4) . . ? C8 C9 C10 120.2(4) . . ? N1 C10 C9 119.0(4) . . ? N1 C10 C11 117.8(3) . . ? C9 C10 C11 123.1(4) . . ? N12 C11 C10 117.5(4) . . ? C11 N12 N13 116.2(3) . . ? N12 N13 C14 120.0(4) . . ? O16 C14 N15 124.0(4) . . ? O16 C14 N13 117.9(4) . . ? N15 C14 N13 118.0(4) . . ? 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 C10 N1 C2 C3 178.5(4) . . . . ? C10 N1 C2 C7 -1.0(5) . . . . ? N1 C2 C3 O3 0.4(5) . . . . ? C7 C2 C3 O3 179.8(3) . . . . ? N1 C2 C3 C4 -179.5(4) . . . . ? C7 C2 C3 C4 0.0(6) . . . . ? O3 C3 C4 C5 179.3(4) . . . . ? C2 C3 C4 C5 -0.9(6) . . . . ? C3 C4 C5 C6 1.3(6) . . . . ? C4 C5 C6 C7 -0.8(7) . . . . ? C5 C6 C7 C2 -0.1(6) . . . . ? C5 C6 C7 C8 178.6(4) . . . . ? N1 C2 C7 C6 179.9(3) . . . . ? C3 C2 C7 C6 0.5(6) . . . . ? N1 C2 C7 C8 1.2(5) . . . . ? C3 C2 C7 C8 -178.3(4) . . . . ? C6 C7 C8 C9 -178.9(4) . . . . ? C2 C7 C8 C9 -0.2(6) . . . . ? C7 C8 C9 C10 -1.1(6) . . . . ? C2 N1 C10 C9 -0.3(6) . . . . ? C2 N1 C10 C11 179.4(3) . . . . ? C8 C9 C10 N1 1.3(6) . . . . ? C8 C9 C10 C11 -178.3(4) . . . . ? N1 C10 C11 N12 -177.6(4) . . . . ? C9 C10 C11 N12 2.0(6) . . . . ? C10 C11 N12 N13 178.3(3) . . . . ? C11 N12 N13 C14 -173.9(4) . . . . ? N12 N13 C14 O16 168.7(3) . . . . ? N12 N13 C14 N15 -11.4(6) . . . . ? _diffrn_measured_fraction_theta_max 0.993 _diffrn_reflns_theta_full 26.30 _diffrn_measured_fraction_theta_full 0.993 _refine_diff_density_max 2.156 _refine_diff_density_min -0.423 _refine_diff_density_rms 0.169 data_fro3166 _database_code_depnum_ccdc_archive 'CCDC 273597' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C12 H14 Cl3 Er N4 O3' _chemical_formula_weight 535.88 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' Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Er Er -0.2586 4.9576 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M P21/n 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 7.982(1) _cell_length_b 19.237(1) _cell_length_c 10.999(1) _cell_angle_alpha 90.00 _cell_angle_beta 95.21(1) _cell_angle_gamma 90.00 _cell_volume 1681.9(3) _cell_formula_units_Z 4 _cell_measurement_temperature 198(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description plate _exptl_crystal_colour yellow _exptl_crystal_size_max 0.30 _exptl_crystal_size_mid 0.15 _exptl_crystal_size_min 0.03 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 2.116 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1028 _exptl_absorpt_coefficient_mu 5.483 _exptl_absorpt_correction_type empirical _exptl_absorpt_correction_T_min 0.2900 _exptl_absorpt_correction_T_max 0.8528 _exptl_absorpt_process_details 'SORTAV (Blessing, 1995 & 1997)' _exptl_special_details ; ? ; _diffrn_ambient_temperature 198(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'rotating anode Nonius FR591' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Nonius KappaCCD' _diffrn_measurement_method '\w and \f scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 10239 _diffrn_reflns_av_R_equivalents 0.0514 _diffrn_reflns_av_sigmaI/netI 0.0417 _diffrn_reflns_limit_h_min -10 _diffrn_reflns_limit_h_max 7 _diffrn_reflns_limit_k_min -25 _diffrn_reflns_limit_k_max 23 _diffrn_reflns_limit_l_min -14 _diffrn_reflns_limit_l_max 14 _diffrn_reflns_theta_min 2.12 _diffrn_reflns_theta_max 27.87 _reflns_number_total 3995 _reflns_number_gt 3659 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Collect (Nonius B.V., 1998)' _computing_cell_refinement 'Collect (nonius B.V., 1998)' _computing_data_reduction 'Denzo-SMN (Otwinowski & Minor, 1997)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'SCHAKAL (Keller, 1997)' _computing_publication_material '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. All remaining difference electron density is located close to Er. ; _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^)+(0.0619P)^2^+0.8690P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens 'at O3 and N from difmap, other geom' _refine_ls_hydrogen_treatment mixed _refine_ls_extinction_method SHELXL _refine_ls_extinction_coef 0.0025(4) _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_number_reflns 3995 _refine_ls_number_parameters 227 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0377 _refine_ls_R_factor_gt 0.0343 _refine_ls_wR_factor_ref 0.0919 _refine_ls_wR_factor_gt 0.0895 _refine_ls_goodness_of_fit_ref 1.030 _refine_ls_restrained_S_all 1.030 _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 Er Er 0.766174(17) 0.139123(8) 0.857886(14) 0.02187(10) Uani 1 1 d . . . Cl1 Cl 0.86399(12) 0.17681(6) 0.65278(9) 0.0364(2) Uani 1 1 d . . . Cl2 Cl 0.64627(11) 0.07198(5) 1.04025(8) 0.02796(19) Uani 1 1 d . . . Cl3 Cl 0.64741(11) 0.25401(5) 0.93234(9) 0.0309(2) Uani 1 1 d . . . N1 N 0.7043(3) 0.02778(16) 0.7579(3) 0.0235(6) Uani 1 1 d . . . C2 C 0.5487(4) 0.0161(2) 0.7016(3) 0.0255(7) Uani 1 1 d . . . C3 C 0.4320(4) 0.0710(2) 0.7012(3) 0.0275(7) Uani 1 1 d . . . O3 O 0.4887(4) 0.13039(15) 0.7600(3) 0.0293(6) Uani 1 1 d . . . H3 H 0.421(9) 0.162(4) 0.742(6) 0.07(2) Uiso 1 1 d . . . C4 C 0.2724(5) 0.0626(3) 0.6450(4) 0.0358(9) Uani 1 1 d . . . H4 H 0.1924 0.0992 0.6445 0.043 Uiso 1 1 calc R . . C5 C 0.2298(5) -0.0014(3) 0.5880(4) 0.0386(10) Uani 1 1 d . . . H5 H 0.1193 -0.0072 0.5494 0.046 Uiso 1 1 calc R . . C6 C 0.3395(5) -0.0552(2) 0.5859(3) 0.0350(9) Uani 1 1 d . . . H6 H 0.3061 -0.0972 0.5455 0.042 Uiso 1 1 calc R . . C7 C 0.5037(5) -0.0482(2) 0.6443(3) 0.0287(8) Uani 1 1 d . . . C8 C 0.6264(5) -0.0997(2) 0.6473(4) 0.0326(8) Uani 1 1 d . . . H8 H 0.6006 -0.1435 0.6102 0.039 Uiso 1 1 calc R . . C9 C 0.7847(5) -0.0877(2) 0.7036(4) 0.0303(8) Uani 1 1 d . . . H9 H 0.8692 -0.1226 0.7054 0.036 Uiso 1 1 calc R . . C10 C 0.8181(4) -0.02269(19) 0.7584(3) 0.0267(7) Uani 1 1 d . . . C11 C 0.9834(4) -0.0066(2) 0.8199(3) 0.0258(7) Uani 1 1 d . . . H11 H 1.0740 -0.0388 0.8230 0.031 Uiso 1 1 calc R . . N12 N 0.9989(3) 0.05374(16) 0.8696(3) 0.0239(6) Uani 1 1 d . . . N13 N 1.1478(4) 0.07504(18) 0.9279(3) 0.0269(7) Uani 1 1 d . . . H13 H 1.214(6) 0.052(3) 0.937(4) 0.029(13) Uiso 1 1 d . . . C14 C 1.1464(5) 0.14025(18) 0.9759(4) 0.0255(8) Uani 1 1 d . . . O15 O 1.0113(3) 0.17412(14) 0.9662(3) 0.0296(6) Uani 1 1 d . . . N16 N 1.2878(4) 0.1643(2) 1.0301(3) 0.0316(7) Uani 1 1 d . . . H16A H 1.298(7) 0.215(4) 1.036(6) 0.067(18) Uiso 1 1 d . . . H16B H 1.360(8) 0.143(3) 1.033(6) 0.042(17) Uiso 1 1 d . . . O17 O 0.3059(6) 0.2319(2) 0.7019(4) 0.0812(16) Uani 1 1 d . . . H17 H 0.3024 0.2447 0.6288 0.122 Uiso 1 1 calc R . . C18 C 0.2422(6) 0.2835(3) 0.7708(5) 0.0453(11) Uani 1 1 d . . . H18A H 0.3043 0.2845 0.8518 0.068 Uiso 1 1 calc R . . H18B H 0.1230 0.2744 0.7792 0.068 Uiso 1 1 calc R . . H18C H 0.2537 0.3285 0.7304 0.068 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 Er 0.01794(12) 0.02177(13) 0.02573(13) 0.00059(5) 0.00109(7) 0.00124(5) Cl1 0.0371(5) 0.0393(5) 0.0337(5) 0.0071(4) 0.0078(4) -0.0013(4) Cl2 0.0254(4) 0.0278(4) 0.0308(4) 0.0043(4) 0.0032(3) 0.0028(3) Cl3 0.0291(4) 0.0249(4) 0.0383(5) -0.0013(4) 0.0019(3) 0.0049(3) N1 0.0188(13) 0.0275(15) 0.0240(14) 0.0018(12) 0.0018(11) -0.0013(11) C2 0.0234(16) 0.036(2) 0.0169(15) -0.0009(14) 0.0012(12) -0.0032(14) C3 0.0215(16) 0.038(2) 0.0234(16) 0.0021(15) 0.0014(13) 0.0000(14) O3 0.0206(13) 0.0320(14) 0.0345(15) -0.0016(12) -0.0021(11) 0.0053(11) C4 0.0231(17) 0.051(3) 0.032(2) 0.0008(18) -0.0011(14) -0.0008(18) C5 0.0263(18) 0.056(3) 0.032(2) 0.001(2) -0.0061(15) -0.0074(18) C6 0.034(2) 0.044(2) 0.0268(18) -0.0013(17) -0.0026(15) -0.0131(18) C7 0.0285(18) 0.034(2) 0.0235(16) -0.0025(15) 0.0030(13) -0.0052(15) C8 0.039(2) 0.029(2) 0.0289(18) -0.0009(16) 0.0017(15) -0.0055(16) C9 0.0296(18) 0.0274(18) 0.0337(19) -0.0022(16) 0.0028(15) 0.0012(15) C10 0.0259(17) 0.0278(18) 0.0266(17) -0.0007(15) 0.0033(14) 0.0003(14) C11 0.0214(15) 0.0272(18) 0.0290(18) 0.0009(15) 0.0030(13) 0.0028(14) N12 0.0173(13) 0.0288(15) 0.0258(14) 0.0024(13) 0.0025(10) -0.0006(11) N13 0.0183(14) 0.0288(17) 0.0327(16) 0.0017(14) -0.0030(12) 0.0052(13) C14 0.0204(17) 0.031(2) 0.0254(19) 0.0044(14) 0.0024(14) 0.0007(12) O15 0.0192(11) 0.0306(14) 0.0384(14) -0.0048(12) -0.0015(10) 0.0032(10) N16 0.0208(15) 0.0319(19) 0.0413(19) -0.0035(16) -0.0024(13) 0.0024(14) O17 0.112(4) 0.073(3) 0.050(2) -0.019(2) -0.037(2) 0.063(3) C18 0.043(2) 0.038(2) 0.054(3) 0.003(2) -0.003(2) 0.0097(19) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag Er O15 2.298(3) . ? Er O3 2.379(3) . ? Er N1 2.438(3) . ? Er N12 2.474(3) . ? Er Cl1 2.5583(10) . ? Er Cl3 2.5680(9) . ? Er Cl2 2.6375(9) . ? N1 C10 1.330(5) . ? N1 C2 1.355(4) . ? C2 C3 1.409(5) . ? C2 C7 1.418(5) . ? C3 O3 1.369(5) . ? C3 C4 1.374(5) . ? C4 C5 1.409(7) . ? C5 C6 1.356(7) . ? C6 C7 1.413(5) . ? C7 C8 1.392(6) . ? C8 C9 1.375(6) . ? C9 C10 1.404(5) . ? C10 C11 1.460(5) . ? C11 N12 1.284(5) . ? N12 N13 1.361(4) . ? N13 C14 1.361(5) . ? C14 O15 1.256(5) . ? C14 N16 1.312(5) . ? O17 C18 1.375(6) . ? 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 O15 Er O3 165.80(10) . . ? O15 Er N1 128.29(9) . . ? O3 Er N1 65.90(10) . . ? O15 Er N12 64.38(10) . . ? O3 Er N12 129.82(10) . . ? N1 Er N12 63.93(10) . . ? O15 Er Cl1 93.48(7) . . ? O3 Er Cl1 88.11(8) . . ? N1 Er Cl1 85.23(7) . . ? N12 Er Cl1 86.92(7) . . ? O15 Er Cl3 84.49(7) . . ? O3 Er Cl3 81.35(7) . . ? N1 Er Cl3 146.56(7) . . ? N12 Er Cl3 148.41(7) . . ? Cl1 Er Cl3 100.86(3) . . ? O15 Er Cl2 95.73(7) . . ? O3 Er Cl2 85.55(8) . . ? N1 Er Cl2 80.80(7) . . ? N12 Er Cl2 87.58(7) . . ? Cl1 Er Cl2 166.01(3) . . ? Cl3 Er Cl2 90.51(3) . . ? C10 N1 C2 118.5(3) . . ? C10 N1 Er 122.0(2) . . ? C2 N1 Er 119.5(2) . . ? N1 C2 C3 117.0(3) . . ? N1 C2 C7 122.2(3) . . ? C3 C2 C7 120.8(3) . . ? O3 C3 C4 124.3(4) . . ? O3 C3 C2 115.8(3) . . ? C4 C3 C2 119.9(4) . . ? C3 O3 Er 121.8(2) . . ? C3 C4 C5 118.7(4) . . ? C6 C5 C4 122.9(4) . . ? C5 C6 C7 119.6(4) . . ? C8 C7 C6 124.4(4) . . ? C8 C7 C2 117.4(3) . . ? C6 C7 C2 118.2(4) . . ? C9 C8 C7 120.5(4) . . ? C8 C9 C10 118.3(4) . . ? N1 C10 C9 123.1(3) . . ? N1 C10 C11 115.8(3) . . ? C9 C10 C11 121.1(3) . . ? N12 C11 C10 115.9(3) . . ? C11 N12 N13 121.2(3) . . ? C11 N12 Er 122.4(2) . . ? N13 N12 Er 116.4(2) . . ? C14 N13 N12 115.0(3) . . ? O15 C14 N16 123.5(4) . . ? O15 C14 N13 118.8(4) . . ? N16 C14 N13 117.7(4) . . ? C14 O15 Er 125.2(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 O15 Er N1 C10 -1.3(3) . . . . ? O3 Er N1 C10 179.4(3) . . . . ? N12 Er N1 C10 0.5(2) . . . . ? Cl1 Er N1 C10 89.4(3) . . . . ? Cl3 Er N1 C10 -168.1(2) . . . . ? Cl2 Er N1 C10 -91.3(3) . . . . ? O15 Er N1 C2 177.6(2) . . . . ? O3 Er N1 C2 -1.6(2) . . . . ? N12 Er N1 C2 179.4(3) . . . . ? Cl1 Er N1 C2 -91.7(2) . . . . ? Cl3 Er N1 C2 10.8(3) . . . . ? Cl2 Er N1 C2 87.6(2) . . . . ? C10 N1 C2 C3 -179.0(3) . . . . ? Er N1 C2 C3 2.0(4) . . . . ? C10 N1 C2 C7 0.5(5) . . . . ? Er N1 C2 C7 -178.5(2) . . . . ? N1 C2 C3 O3 -0.9(5) . . . . ? C7 C2 C3 O3 179.6(3) . . . . ? N1 C2 C3 C4 179.6(3) . . . . ? C7 C2 C3 C4 0.1(5) . . . . ? C4 C3 O3 Er 178.8(3) . . . . ? C2 C3 O3 Er -0.6(4) . . . . ? O15 Er O3 C3 -176.5(3) . . . . ? N1 Er O3 C3 1.1(2) . . . . ? N12 Er O3 C3 2.3(3) . . . . ? Cl1 Er O3 C3 86.8(3) . . . . ? Cl3 Er O3 C3 -172.0(3) . . . . ? Cl2 Er O3 C3 -80.8(3) . . . . ? O3 C3 C4 C5 -179.8(4) . . . . ? C2 C3 C4 C5 -0.3(6) . . . . ? C3 C4 C5 C6 -0.2(6) . . . . ? C4 C5 C6 C7 0.9(6) . . . . ? C5 C6 C7 C8 -179.7(4) . . . . ? C5 C6 C7 C2 -1.1(5) . . . . ? N1 C2 C7 C8 -0.2(5) . . . . ? C3 C2 C7 C8 179.3(3) . . . . ? N1 C2 C7 C6 -178.8(3) . . . . ? C3 C2 C7 C6 0.7(5) . . . . ? C6 C7 C8 C9 178.3(4) . . . . ? C2 C7 C8 C9 -0.3(5) . . . . ? C7 C8 C9 C10 0.5(6) . . . . ? C2 N1 C10 C9 -0.2(5) . . . . ? Er N1 C10 C9 178.7(3) . . . . ? C2 N1 C10 C11 179.7(3) . . . . ? Er N1 C10 C11 -1.4(4) . . . . ? C8 C9 C10 N1 -0.2(6) . . . . ? C8 C9 C10 C11 179.9(3) . . . . ? N1 C10 C11 N12 1.9(5) . . . . ? C9 C10 C11 N12 -178.2(3) . . . . ? C10 C11 N12 N13 -178.9(3) . . . . ? C10 C11 N12 Er -1.5(4) . . . . ? O15 Er N12 C11 179.1(3) . . . . ? O3 Er N12 C11 -0.6(3) . . . . ? N1 Er N12 C11 0.6(3) . . . . ? Cl1 Er N12 C11 -85.6(3) . . . . ? Cl3 Er N12 C11 168.6(2) . . . . ? Cl2 Er N12 C11 81.6(3) . . . . ? O15 Er N12 N13 -3.4(2) . . . . ? O3 Er N12 N13 176.9(2) . . . . ? N1 Er N12 N13 178.1(3) . . . . ? Cl1 Er N12 N13 91.9(2) . . . . ? Cl3 Er N12 N13 -13.9(3) . . . . ? Cl2 Er N12 N13 -100.9(2) . . . . ? C11 N12 N13 C14 179.7(3) . . . . ? Er N12 N13 C14 2.2(4) . . . . ? N12 N13 C14 O15 1.9(5) . . . . ? N12 N13 C14 N16 -178.1(4) . . . . ? N16 C14 O15 Er 174.2(3) . . . . ? N13 C14 O15 Er -5.8(5) . . . . ? O3 Er O15 C14 -176.0(4) . . . . ? N1 Er O15 C14 6.7(3) . . . . ? N12 Er O15 C14 4.9(3) . . . . ? Cl1 Er O15 C14 -80.0(3) . . . . ? Cl3 Er O15 C14 179.4(3) . . . . ? Cl2 Er O15 C14 89.5(3) . . . . ? _diffrn_measured_fraction_theta_max 0.994 _diffrn_reflns_theta_full 27.87 _diffrn_measured_fraction_theta_full 0.994 _refine_diff_density_max 1.457 _refine_diff_density_min -2.075 _refine_diff_density_rms 0.178 data_fro3168 _database_code_depnum_ccdc_archive 'CCDC 273598' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C12 H14 Cl3 Ho N4 O3' _chemical_formula_weight 533.55 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' Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Ho Ho -0.2175 4.6783 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M P21/n 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 8.001(1) _cell_length_b 19.276(1) _cell_length_c 11.010(1) _cell_angle_alpha 90.00 _cell_angle_beta 95.35(1) _cell_angle_gamma 90.00 _cell_volume 1690.6(3) _cell_formula_units_Z 4 _cell_measurement_temperature 198(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description plate _exptl_crystal_colour yellow _exptl_crystal_size_max 0.45 _exptl_crystal_size_mid 0.45 _exptl_crystal_size_min 0.08 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 2.096 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1024 _exptl_absorpt_coefficient_mu 5.171 _exptl_absorpt_correction_type empirical _exptl_absorpt_correction_T_min 0.2043 _exptl_absorpt_correction_T_max 0.6824 _exptl_absorpt_process_details 'SORTAV (Blessing, 1995 & 1997)' _exptl_special_details ; ? ; _diffrn_ambient_temperature 198(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'rotating anode Nonius FR591' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Nonius KappaCCD' _diffrn_measurement_method '\w and \f scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 10619 _diffrn_reflns_av_R_equivalents 0.0532 _diffrn_reflns_av_sigmaI/netI 0.0385 _diffrn_reflns_limit_h_min -10 _diffrn_reflns_limit_h_max 9 _diffrn_reflns_limit_k_min -25 _diffrn_reflns_limit_k_max 23 _diffrn_reflns_limit_l_min -14 _diffrn_reflns_limit_l_max 13 _diffrn_reflns_theta_min 2.11 _diffrn_reflns_theta_max 27.88 _reflns_number_total 4012 _reflns_number_gt 3823 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Collect (Nonius B.V., 1998)' _computing_cell_refinement 'Collect (Nonius B.V., 1998)' _computing_data_reduction 'Denzo-SMN (Otwinowski & Minor, 1997)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'SCHAKAL (Keller, 1997)' _computing_publication_material '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. The remaining electron density is located close to Ho. ; _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^)+(0.0710P)^2^+1.4685P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens 'at O3 and N from difmap, other geom' _refine_ls_hydrogen_treatment mixed _refine_ls_extinction_method SHELXL _refine_ls_extinction_coef 0.0052(6) _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_number_reflns 4012 _refine_ls_number_parameters 219 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0393 _refine_ls_R_factor_gt 0.0380 _refine_ls_wR_factor_ref 0.1031 _refine_ls_wR_factor_gt 0.1018 _refine_ls_goodness_of_fit_ref 1.083 _refine_ls_restrained_S_all 1.083 _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 Ho Ho 0.765687(18) 0.139510(8) 0.858254(13) 0.02179(11) Uani 1 1 d . . . Cl1 Cl 0.86284(13) 0.17719(6) 0.65190(9) 0.0362(2) Uani 1 1 d . . . Cl2 Cl 0.64622(11) 0.07189(5) 1.04132(8) 0.02799(19) Uani 1 1 d . . . Cl3 Cl 0.64633(12) 0.25451(5) 0.93276(9) 0.0316(2) Uani 1 1 d . . . N1 N 0.7039(4) 0.02752(16) 0.7577(3) 0.0230(6) Uani 1 1 d . . . C2 C 0.5495(4) 0.0157(2) 0.7016(3) 0.0254(7) Uani 1 1 d . . . C3 C 0.4304(5) 0.0704(2) 0.7015(3) 0.0265(7) Uani 1 1 d . . . O3 O 0.4868(4) 0.12966(15) 0.7599(3) 0.0294(6) Uani 1 1 d . . . H3 H 0.398(10) 0.173(5) 0.723(7) 0.08(2) Uiso 1 1 d . . . C4 C 0.2722(5) 0.0615(3) 0.6454(3) 0.0339(8) Uani 1 1 d . . . H4 H 0.1918 0.0978 0.6446 0.041 Uiso 1 1 calc R . . C5 C 0.2302(5) -0.0031(3) 0.5882(4) 0.0387(9) Uani 1 1 d . . . H5 H 0.1200 -0.0093 0.5496 0.046 Uiso 1 1 calc R . . C6 C 0.3406(5) -0.0560(2) 0.5865(4) 0.0356(9) Uani 1 1 d . . . H6 H 0.3081 -0.0983 0.5467 0.043 Uiso 1 1 calc R . . C7 C 0.5041(5) -0.0481(2) 0.6439(3) 0.0288(7) Uani 1 1 d . . . C8 C 0.6270(5) -0.0997(2) 0.6465(4) 0.0325(8) Uani 1 1 d . . . H8 H 0.6015 -0.1433 0.6090 0.039 Uiso 1 1 calc R . . C9 C 0.7848(5) -0.0876(2) 0.7033(3) 0.0301(8) Uani 1 1 d . . . H9 H 0.8692 -0.1223 0.7055 0.036 Uiso 1 1 calc R . . C10 C 0.8182(5) -0.02243(19) 0.7581(3) 0.0253(7) Uani 1 1 d . . . C11 C 0.9834(4) -0.0060(2) 0.8194(3) 0.0260(7) Uani 1 1 d . . . H11 H 1.0741 -0.0380 0.8219 0.031 Uiso 1 1 calc R . . N12 N 0.9988(3) 0.05381(16) 0.8697(3) 0.0233(6) Uani 1 1 d . . . N13 N 1.1486(4) 0.07471(18) 0.9279(3) 0.0275(7) Uani 1 1 d . . . H13 H 1.218(6) 0.054(3) 0.933(4) 0.020(11) Uiso 1 1 d . . . C14 C 1.1475(5) 0.13955(17) 0.9764(4) 0.0245(8) Uani 1 1 d . . . O15 O 1.0127(3) 0.17394(15) 0.9669(3) 0.0303(6) Uani 1 1 d . . . N16 N 1.2888(4) 0.1638(2) 1.0302(3) 0.0315(7) Uani 1 1 d . . . H16A H 1.2891 0.2032 1.0626 0.038 Uiso 1 1 d R . . H16B H 1.3913 0.1366 1.0218 0.038 Uiso 1 1 d R . . O17 O 0.3016(7) 0.2304(3) 0.7025(4) 0.0845(18) Uani 1 1 d . . . H17 H 0.3007 0.2436 0.6297 0.127 Uiso 1 1 calc R . . C18 C 0.2418(7) 0.2827(3) 0.7713(5) 0.0464(11) Uani 1 1 d . . . H18A H 0.3046 0.2832 0.8521 0.070 Uiso 1 1 calc R . . H18B H 0.1226 0.2748 0.7801 0.070 Uiso 1 1 calc R . . H18C H 0.2556 0.3273 0.7308 0.070 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 Ho 0.01875(14) 0.02275(15) 0.02357(14) 0.00073(5) 0.00039(8) 0.00133(5) Cl1 0.0381(5) 0.0408(5) 0.0302(4) 0.0075(4) 0.0070(4) -0.0031(4) Cl2 0.0271(4) 0.0288(4) 0.0282(4) 0.0047(3) 0.0028(3) 0.0033(3) Cl3 0.0310(5) 0.0261(4) 0.0373(5) -0.0013(3) 0.0010(4) 0.0050(3) N1 0.0199(13) 0.0273(15) 0.0213(13) 0.0000(11) -0.0007(10) 0.0001(11) C2 0.0227(16) 0.0336(19) 0.0194(15) 0.0012(13) -0.0006(12) -0.0037(14) C3 0.0234(16) 0.0338(19) 0.0217(15) 0.0009(13) -0.0015(13) -0.0001(14) O3 0.0230(13) 0.0313(13) 0.0324(14) -0.0021(11) -0.0047(11) 0.0052(11) C4 0.0212(16) 0.050(2) 0.0298(19) 0.0027(16) -0.0031(13) -0.0024(17) C5 0.0279(18) 0.056(3) 0.0303(19) 0.0022(18) -0.0067(15) -0.0115(18) C6 0.033(2) 0.044(2) 0.0277(17) -0.0024(16) -0.0043(15) -0.0123(17) C7 0.0287(17) 0.036(2) 0.0213(15) -0.0004(14) 0.0014(13) -0.0066(15) C8 0.042(2) 0.0270(18) 0.0285(17) -0.0025(14) 0.0012(15) -0.0063(16) C9 0.0328(19) 0.0281(18) 0.0291(17) -0.0028(14) 0.0012(14) 0.0002(15) C10 0.0276(17) 0.0265(17) 0.0218(15) 0.0002(12) 0.0023(13) 0.0015(14) C11 0.0225(15) 0.0276(17) 0.0277(16) 0.0017(13) 0.0016(13) 0.0049(13) N12 0.0177(13) 0.0286(15) 0.0234(13) 0.0019(11) 0.0013(10) -0.0001(11) N13 0.0180(15) 0.0315(17) 0.0318(16) -0.0008(13) -0.0047(12) 0.0026(13) C14 0.0213(18) 0.028(2) 0.0233(17) 0.0032(12) 0.0002(14) 0.0002(12) O15 0.0203(12) 0.0317(14) 0.0377(14) -0.0060(11) -0.0031(10) 0.0023(10) N16 0.0205(14) 0.0346(18) 0.0380(17) -0.0039(14) -0.0036(12) -0.0011(13) O17 0.116(4) 0.076(3) 0.053(2) -0.021(2) -0.042(3) 0.063(3) C18 0.048(3) 0.040(2) 0.048(3) 0.003(2) -0.011(2) 0.010(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 Ho O15 2.310(3) . ? Ho O3 2.395(3) . ? Ho N1 2.455(3) . ? Ho N12 2.486(3) . ? Ho Cl1 2.5735(10) . ? Ho Cl3 2.5778(9) . ? Ho Cl2 2.6522(9) . ? N1 C10 1.328(5) . ? N1 C2 1.348(4) . ? C2 C7 1.416(5) . ? C2 C3 1.420(5) . ? C3 C4 1.367(5) . ? C3 O3 1.367(5) . ? C4 C5 1.421(7) . ? C5 C6 1.350(7) . ? C6 C7 1.408(5) . ? C7 C8 1.398(6) . ? C8 C9 1.376(6) . ? C9 C10 1.408(5) . ? C10 C11 1.461(5) . ? C11 N12 1.280(5) . ? N12 N13 1.366(4) . ? N13 C14 1.359(5) . ? C14 O15 1.262(5) . ? C14 N16 1.313(5) . ? O17 C18 1.372(6) . ? 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 O15 Ho O3 166.61(10) . . ? O15 Ho N1 127.78(10) . . ? O3 Ho N1 65.58(10) . . ? O15 Ho N12 64.10(10) . . ? O3 Ho N12 129.28(10) . . ? N1 Ho N12 63.71(10) . . ? O15 Ho Cl1 93.55(8) . . ? O3 Ho Cl1 88.20(8) . . ? N1 Ho Cl1 85.11(7) . . ? N12 Ho Cl1 86.86(7) . . ? O15 Ho Cl3 84.98(7) . . ? O3 Ho Cl3 81.65(7) . . ? N1 Ho Cl3 146.58(7) . . ? N12 Ho Cl3 148.63(7) . . ? Cl1 Ho Cl3 100.93(3) . . ? O15 Ho Cl2 95.69(8) . . ? O3 Ho Cl2 85.30(8) . . ? N1 Ho Cl2 80.73(7) . . ? N12 Ho Cl2 87.53(7) . . ? Cl1 Ho Cl2 165.82(3) . . ? Cl3 Ho Cl2 90.59(3) . . ? C10 N1 C2 118.8(3) . . ? C10 N1 Ho 121.8(2) . . ? C2 N1 Ho 119.5(2) . . ? N1 C2 C7 122.5(3) . . ? N1 C2 C3 117.5(3) . . ? C7 C2 C3 120.0(3) . . ? C4 C3 O3 124.6(4) . . ? C4 C3 C2 120.0(4) . . ? O3 C3 C2 115.3(3) . . ? C3 O3 Ho 122.1(2) . . ? C3 C4 C5 118.8(4) . . ? C6 C5 C4 122.7(4) . . ? C5 C6 C7 119.6(4) . . ? C8 C7 C6 123.7(4) . . ? C8 C7 C2 117.3(3) . . ? C6 C7 C2 119.0(4) . . ? C9 C8 C7 120.1(4) . . ? C8 C9 C10 118.5(4) . . ? N1 C10 C9 122.8(3) . . ? N1 C10 C11 116.0(3) . . ? C9 C10 C11 121.2(3) . . ? N12 C11 C10 116.2(3) . . ? C11 N12 N13 120.9(3) . . ? C11 N12 Ho 122.4(2) . . ? N13 N12 Ho 116.7(2) . . ? C14 N13 N12 114.7(3) . . ? O15 C14 N16 123.0(3) . . ? O15 C14 N13 119.2(3) . . ? N16 C14 N13 117.8(4) . . ? C14 O15 Ho 125.1(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 O15 Ho N1 C10 -1.5(3) . . . . ? O3 Ho N1 C10 179.4(3) . . . . ? N12 Ho N1 C10 0.3(2) . . . . ? Cl1 Ho N1 C10 89.2(3) . . . . ? Cl3 Ho N1 C10 -168.4(2) . . . . ? Cl2 Ho N1 C10 -91.6(3) . . . . ? O15 Ho N1 C2 177.7(2) . . . . ? O3 Ho N1 C2 -1.3(2) . . . . ? N12 Ho N1 C2 179.5(3) . . . . ? Cl1 Ho N1 C2 -91.6(2) . . . . ? Cl3 Ho N1 C2 10.9(3) . . . . ? Cl2 Ho N1 C2 87.7(2) . . . . ? C10 N1 C2 C7 0.5(5) . . . . ? Ho N1 C2 C7 -178.7(3) . . . . ? C10 N1 C2 C3 -179.4(3) . . . . ? Ho N1 C2 C3 1.4(4) . . . . ? N1 C2 C3 C4 179.6(3) . . . . ? C7 C2 C3 C4 -0.3(5) . . . . ? N1 C2 C3 O3 -0.3(5) . . . . ? C7 C2 C3 O3 179.8(3) . . . . ? C4 C3 O3 Ho 179.1(3) . . . . ? C2 C3 O3 Ho -1.0(4) . . . . ? O15 Ho O3 C3 -175.5(4) . . . . ? N1 Ho O3 C3 1.2(3) . . . . ? N12 Ho O3 C3 2.2(3) . . . . ? Cl1 Ho O3 C3 86.7(3) . . . . ? Cl3 Ho O3 C3 -172.0(3) . . . . ? Cl2 Ho O3 C3 -80.7(3) . . . . ? O3 C3 C4 C5 -179.9(4) . . . . ? C2 C3 C4 C5 0.2(6) . . . . ? C3 C4 C5 C6 -0.3(6) . . . . ? C4 C5 C6 C7 0.5(6) . . . . ? C5 C6 C7 C8 -179.8(4) . . . . ? C5 C6 C7 C2 -0.5(6) . . . . ? N1 C2 C7 C8 -0.2(5) . . . . ? C3 C2 C7 C8 179.7(3) . . . . ? N1 C2 C7 C6 -179.5(3) . . . . ? C3 C2 C7 C6 0.4(5) . . . . ? C6 C7 C8 C9 179.2(4) . . . . ? C2 C7 C8 C9 -0.1(6) . . . . ? C7 C8 C9 C10 0.1(6) . . . . ? C2 N1 C10 C9 -0.6(5) . . . . ? Ho N1 C10 C9 178.6(3) . . . . ? C2 N1 C10 C11 179.4(3) . . . . ? Ho N1 C10 C11 -1.3(4) . . . . ? C8 C9 C10 N1 0.3(6) . . . . ? C8 C9 C10 C11 -179.7(3) . . . . ? N1 C10 C11 N12 2.2(5) . . . . ? C9 C10 C11 N12 -177.8(3) . . . . ? C10 C11 N12 N13 -179.1(3) . . . . ? C10 C11 N12 Ho -2.1(4) . . . . ? O15 Ho N12 C11 179.5(3) . . . . ? O3 Ho N12 C11 0.0(3) . . . . ? N1 Ho N12 C11 1.0(3) . . . . ? Cl1 Ho N12 C11 -85.1(3) . . . . ? Cl3 Ho N12 C11 169.0(2) . . . . ? Cl2 Ho N12 C11 81.9(3) . . . . ? O15 Ho N12 N13 -3.4(2) . . . . ? O3 Ho N12 N13 177.2(2) . . . . ? N1 Ho N12 N13 178.2(3) . . . . ? Cl1 Ho N12 N13 92.1(2) . . . . ? Cl3 Ho N12 N13 -13.9(3) . . . . ? Cl2 Ho N12 N13 -101.0(2) . . . . ? C11 N12 N13 C14 179.6(3) . . . . ? Ho N12 N13 C14 2.4(4) . . . . ? N12 N13 C14 O15 1.5(5) . . . . ? N12 N13 C14 N16 -177.8(3) . . . . ? N16 C14 O15 Ho 173.9(3) . . . . ? N13 C14 O15 Ho -5.4(5) . . . . ? O3 Ho O15 C14 -177.2(4) . . . . ? N1 Ho O15 C14 6.5(4) . . . . ? N12 Ho O15 C14 4.7(3) . . . . ? Cl1 Ho O15 C14 -80.1(3) . . . . ? Cl3 Ho O15 C14 179.2(3) . . . . ? Cl2 Ho O15 C14 89.2(3) . . . . ? _diffrn_measured_fraction_theta_max 0.992 _diffrn_reflns_theta_full 27.88 _diffrn_measured_fraction_theta_full 0.992 _refine_diff_density_max 2.531 _refine_diff_density_min -2.404 _refine_diff_density_rms 0.222 data_fro3203 _database_code_depnum_ccdc_archive 'CCDC 273599' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C29 H39 N8 O8 Y' _chemical_formula_weight 716.59 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' Y Y -2.7962 3.5667 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M P21/n 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 16.147(1) _cell_length_b 11.664(1) _cell_length_c 18.932(1) _cell_angle_alpha 90.00 _cell_angle_beta 106.87(1) _cell_angle_gamma 90.00 _cell_volume 3412.2(4) _cell_formula_units_Z 4 _cell_measurement_temperature 198(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description plate _exptl_crystal_colour red _exptl_crystal_size_max 0.15 _exptl_crystal_size_mid 0.10 _exptl_crystal_size_min 0.05 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.395 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1488 _exptl_absorpt_coefficient_mu 1.767 _exptl_absorpt_correction_type empirical _exptl_absorpt_correction_T_min 0.7775 _exptl_absorpt_correction_T_max 0.9168 _exptl_absorpt_process_details 'SORTAV (Blessing, 1995 & 1997)' _exptl_special_details ; ? ; _diffrn_ambient_temperature 198(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'rotating anode Nonius FR591' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Nonius KappaCCD' _diffrn_measurement_method '\w and \f scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 26738 _diffrn_reflns_av_R_equivalents 0.0865 _diffrn_reflns_av_sigmaI/netI 0.0719 _diffrn_reflns_limit_h_min -18 _diffrn_reflns_limit_h_max 19 _diffrn_reflns_limit_k_min -13 _diffrn_reflns_limit_k_max 13 _diffrn_reflns_limit_l_min -22 _diffrn_reflns_limit_l_max 20 _diffrn_reflns_theta_min 2.08 _diffrn_reflns_theta_max 25.00 _reflns_number_total 5998 _reflns_number_gt 4325 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Collect (Nonius B.V., 1998)' _computing_cell_refinement 'Collect (Nonius B.V., 1998)' _computing_data_reduction 'Denzo-SMN (Otwinowski & Minor, 1997)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'SCHAKAL (Keller, 1997)' _computing_publication_material '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. Due to crystal size diffracting power is weak, ether molecule refined with isotropic thermal displacement parameters, and geometrical restraints (SADI). ; _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^)+(0.0675P)^2^+7.8766P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens 'at N from difmap, other geom' _refine_ls_hydrogen_treatment mixed _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 5998 _refine_ls_number_parameters 418 _refine_ls_number_restraints 3 _refine_ls_R_factor_all 0.0957 _refine_ls_R_factor_gt 0.0582 _refine_ls_wR_factor_ref 0.1531 _refine_ls_wR_factor_gt 0.1363 _refine_ls_goodness_of_fit_ref 1.054 _refine_ls_restrained_S_all 1.055 _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 Y Y 0.16882(3) 0.18446(4) 0.07327(2) 0.02399(16) Uani 1 1 d . . . N11 N 0.3010(3) 0.0830(3) 0.0731(2) 0.0274(9) Uani 1 1 d . . . C12 C 0.2980(3) 0.0156(4) 0.0141(3) 0.0296(11) Uani 1 1 d . . . C13 C 0.2172(3) 0.0130(4) -0.0421(3) 0.0310(12) Uani 1 1 d . . . O13 O 0.1521(2) 0.0724(3) -0.03185(17) 0.0303(8) Uani 1 1 d . . . C14 C 0.2130(4) -0.0531(5) -0.1033(3) 0.0433(14) Uani 1 1 d . . . H14 H 0.1607 -0.0558 -0.1426 0.052 Uiso 1 1 calc R . . C15 C 0.2851(4) -0.1165(6) -0.1085(4) 0.0553(17) Uani 1 1 d . . . H15 H 0.2795 -0.1624 -0.1510 0.066 Uiso 1 1 calc R . . C16 C 0.3626(4) -0.1149(6) -0.0550(4) 0.0538(17) Uani 1 1 d . . . H16 H 0.4102 -0.1582 -0.0605 0.065 Uiso 1 1 calc R . . C17 C 0.3709(3) -0.0477(5) 0.0088(3) 0.0396(13) Uani 1 1 d . . . C18 C 0.4467(4) -0.0357(5) 0.0679(3) 0.0471(15) Uani 1 1 d . . . H18 H 0.4971 -0.0769 0.0671 0.056 Uiso 1 1 calc R . . C19 C 0.4493(3) 0.0336(5) 0.1262(3) 0.0428(14) Uani 1 1 d . . . H19 H 0.5011 0.0415 0.1655 0.051 Uiso 1 1 calc R . . C20 C 0.3742(3) 0.0934(4) 0.1274(3) 0.0306(12) Uani 1 1 d . . . C21 C 0.3698(3) 0.1673(4) 0.1881(3) 0.0320(12) Uani 1 1 d . . . H21 H 0.4190 0.1815 0.2291 0.038 Uiso 1 1 calc R . . N22 N 0.2955(3) 0.2124(3) 0.1834(2) 0.0279(9) Uani 1 1 d . . . N23 N 0.2876(3) 0.2815(4) 0.2390(2) 0.0348(10) Uani 1 1 d . . . C24 C 0.2052(3) 0.3167(5) 0.2241(3) 0.0331(12) Uani 1 1 d . . . N25 N 0.1897(4) 0.3905(5) 0.2737(3) 0.0523(15) Uani 1 1 d . . . H25A H 0.229(4) 0.410(5) 0.306(3) 0.046(19) Uiso 1 1 d . . . H25B H 0.135(4) 0.411(5) 0.271(3) 0.048(18) Uiso 1 1 d . . . O26 O 0.1430(2) 0.2868(3) 0.16930(18) 0.0334(8) Uani 1 1 d . . . N31 N 0.0576(2) 0.3054(3) -0.0087(2) 0.0268(9) Uani 1 1 d . . . C32 C 0.0857(3) 0.3974(4) -0.0384(3) 0.0300(12) Uani 1 1 d . . . C33 C 0.1775(3) 0.4141(4) -0.0160(3) 0.0323(12) Uani 1 1 d . . . O33 O 0.2262(2) 0.3378(3) 0.02988(18) 0.0327(8) Uani 1 1 d . . . C34 C 0.2083(4) 0.5087(5) -0.0435(3) 0.0427(14) Uani 1 1 d . . . H34 H 0.2688 0.5232 -0.0298 0.051 Uiso 1 1 calc R . . C35 C 0.1506(4) 0.5852(5) -0.0924(3) 0.0484(15) Uani 1 1 d . . . H35 H 0.1740 0.6495 -0.1109 0.058 Uiso 1 1 calc R . . C36 C 0.0638(4) 0.5701(5) -0.1137(3) 0.0460(15) Uani 1 1 d . . . H36 H 0.0270 0.6234 -0.1460 0.055 Uiso 1 1 calc R . . C37 C 0.0283(4) 0.4735(4) -0.0871(3) 0.0354(13) Uani 1 1 d . . . C38 C -0.0603(4) 0.4481(5) -0.1039(3) 0.0408(14) Uani 1 1 d . . . H38 H -0.1011 0.4969 -0.1364 0.049 Uiso 1 1 calc R . . C39 C -0.0890(3) 0.3545(5) -0.0742(3) 0.0363(13) Uani 1 1 d . . . H39 H -0.1490 0.3371 -0.0864 0.044 Uiso 1 1 calc R . . C40 C -0.0272(3) 0.2848(4) -0.0251(3) 0.0268(11) Uani 1 1 d . . . C41 C -0.0502(3) 0.1839(4) 0.0114(3) 0.0286(11) Uani 1 1 d . . . H41 H -0.1086 0.1610 0.0038 0.034 Uiso 1 1 calc R . . N42 N 0.0132(2) 0.1287(3) 0.0543(2) 0.0251(9) Uani 1 1 d . . . N43 N -0.0018(3) 0.0348(4) 0.0910(2) 0.0267(9) Uani 1 1 d . . . H43 H -0.053(4) 0.005(6) 0.078(3) 0.07(2) Uiso 1 1 d . . . C44 C 0.0718(3) -0.0199(4) 0.1313(2) 0.0261(11) Uani 1 1 d . . . N45 N 0.0603(4) -0.1133(4) 0.1676(3) 0.0363(11) Uani 1 1 d . . . H45A H 0.009(4) -0.124(4) 0.173(3) 0.027(14) Uiso 1 1 d . . . H45B H 0.101(5) -0.145(6) 0.197(4) 0.06(2) Uiso 1 1 d . . . O46 O 0.1453(2) 0.0160(3) 0.13303(17) 0.0291(8) Uani 1 1 d . . . O51 O 0.3927(3) 0.3449(4) 0.0336(2) 0.0611(12) Uani 1 1 d . . . H51 H 0.3422 0.3494 0.0372 0.092 Uiso 1 1 calc R . . C52 C 0.3909(5) 0.2901(6) -0.0327(4) 0.0662(19) Uani 1 1 d . . . H52A H 0.4466 0.3009 -0.0427 0.099 Uiso 1 1 calc R . . H52B H 0.3446 0.3232 -0.0732 0.099 Uiso 1 1 calc R . . H52C H 0.3801 0.2081 -0.0287 0.099 Uiso 1 1 calc R . . O53 O -0.0755(3) -0.2004(7) 0.2166(3) 0.101(2) Uani 1 1 d . . . H53 H -0.0648 -0.1946 0.2626 0.151 Uiso 1 1 calc R . . C54 C -0.1508(5) -0.2589(9) 0.1888(4) 0.090(3) Uani 1 1 d . . . H54A H -0.1908 -0.2400 0.2173 0.135 Uiso 1 1 calc R . . H54B H -0.1391 -0.3414 0.1921 0.135 Uiso 1 1 calc R . . H54C H -0.1768 -0.2373 0.1371 0.135 Uiso 1 1 calc R . . O55 O 0.4559(3) -0.3316(5) -0.1368(3) 0.0677(13) Uani 1 1 d . . . H55 H 0.5083 -0.3421 -0.1139 0.101 Uiso 1 1 calc R . . C56 C 0.4050(5) -0.4148(8) -0.1147(5) 0.094(3) Uani 1 1 d . . . H56A H 0.4412 -0.4806 -0.0932 0.140 Uiso 1 1 calc R . . H56B H 0.3583 -0.4399 -0.1577 0.140 Uiso 1 1 calc R . . H56C H 0.3801 -0.3815 -0.0780 0.140 Uiso 1 1 calc R . . O61 O 0.5014(7) 0.7195(10) 0.1901(6) 0.191(4) Uiso 1 1 d D . . C62 C 0.5864(8) 0.7352(11) 0.2285(7) 0.140(4) Uiso 1 1 d D . . H62A H 0.5883 0.7321 0.2812 0.169 Uiso 1 1 calc R . . H62B H 0.6164 0.6653 0.2192 0.169 Uiso 1 1 calc R . . C63 C 0.6380(11) 0.8220(16) 0.2234(10) 0.245(10) Uiso 1 1 d D . . H63A H 0.6348 0.8343 0.1715 0.368 Uiso 1 1 calc R . . H63B H 0.6977 0.8038 0.2515 0.368 Uiso 1 1 calc R . . H63C H 0.6193 0.8917 0.2434 0.368 Uiso 1 1 calc R . . C64 C 0.4457(13) 0.6304(15) 0.1830(11) 0.267(10) Uiso 1 1 d D . . H64A H 0.4784 0.5625 0.1747 0.321 Uiso 1 1 calc R . . H64B H 0.4380 0.6203 0.2326 0.321 Uiso 1 1 calc R . . C65 C 0.3670(11) 0.6181(15) 0.1363(10) 0.214(7) Uiso 1 1 d D . . H65A H 0.3397 0.6935 0.1246 0.322 Uiso 1 1 calc R . . H65B H 0.3319 0.5700 0.1589 0.322 Uiso 1 1 calc R . . H65C H 0.3713 0.5817 0.0908 0.322 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 Y 0.0210(3) 0.0221(3) 0.0266(2) -0.0006(2) 0.00339(17) 0.0010(2) N11 0.027(2) 0.022(2) 0.033(2) -0.0010(18) 0.0089(18) 0.0016(18) C12 0.023(3) 0.028(3) 0.039(3) -0.003(2) 0.013(2) -0.001(2) C13 0.028(3) 0.030(3) 0.038(3) -0.006(2) 0.014(2) -0.006(2) O13 0.0238(18) 0.033(2) 0.0325(18) -0.0062(15) 0.0058(14) -0.0004(16) C14 0.035(3) 0.052(4) 0.044(3) -0.018(3) 0.013(3) -0.004(3) C15 0.055(4) 0.059(4) 0.060(4) -0.030(3) 0.029(3) -0.004(3) C16 0.040(4) 0.057(4) 0.069(4) -0.023(3) 0.024(3) 0.006(3) C17 0.032(3) 0.037(3) 0.053(3) -0.009(3) 0.018(3) 0.001(3) C18 0.026(3) 0.047(4) 0.069(4) -0.009(3) 0.015(3) 0.012(3) C19 0.025(3) 0.046(4) 0.053(3) -0.002(3) 0.004(2) 0.004(3) C20 0.020(3) 0.031(3) 0.039(3) 0.003(2) 0.006(2) 0.000(2) C21 0.023(3) 0.031(3) 0.035(3) -0.003(2) -0.001(2) 0.002(2) N22 0.026(2) 0.026(2) 0.031(2) -0.0027(17) 0.0068(18) 0.0001(18) N23 0.033(3) 0.033(3) 0.034(2) -0.0079(19) 0.0020(19) 0.004(2) C24 0.037(3) 0.030(3) 0.029(3) -0.004(2) 0.005(2) 0.004(3) N25 0.041(3) 0.062(4) 0.046(3) -0.025(3) 0.000(3) 0.010(3) O26 0.0271(19) 0.037(2) 0.0325(19) -0.0087(15) 0.0029(15) 0.0051(16) N31 0.027(2) 0.024(2) 0.027(2) 0.0034(17) 0.0045(17) 0.0034(18) C32 0.037(3) 0.024(3) 0.030(3) 0.001(2) 0.011(2) 0.003(2) C33 0.034(3) 0.027(3) 0.037(3) 0.002(2) 0.012(2) 0.001(2) O33 0.0257(19) 0.030(2) 0.0401(19) 0.0079(16) 0.0065(15) -0.0017(15) C34 0.042(3) 0.039(3) 0.050(3) 0.006(3) 0.019(3) -0.001(3) C35 0.059(4) 0.036(4) 0.054(4) 0.013(3) 0.022(3) 0.002(3) C36 0.054(4) 0.036(4) 0.048(3) 0.017(3) 0.016(3) 0.009(3) C37 0.042(3) 0.029(3) 0.036(3) 0.003(2) 0.012(2) 0.010(3) C38 0.045(4) 0.039(3) 0.034(3) 0.004(2) 0.003(2) 0.015(3) C39 0.030(3) 0.034(3) 0.040(3) 0.003(2) 0.003(2) 0.007(2) C40 0.026(3) 0.021(3) 0.031(3) -0.001(2) 0.004(2) 0.004(2) C41 0.020(2) 0.027(3) 0.036(3) -0.006(2) 0.003(2) -0.002(2) N42 0.023(2) 0.023(2) 0.026(2) 0.0007(17) 0.0038(17) 0.0024(18) N43 0.022(2) 0.023(2) 0.032(2) 0.0027(18) 0.0033(18) -0.0029(19) C44 0.025(3) 0.024(3) 0.027(2) -0.003(2) 0.004(2) -0.002(2) N45 0.027(3) 0.037(3) 0.041(3) 0.011(2) 0.004(2) -0.003(2) O46 0.0224(18) 0.0276(19) 0.0343(18) 0.0071(15) 0.0035(14) 0.0026(15) O51 0.038(2) 0.084(4) 0.063(3) 0.007(2) 0.018(2) -0.001(2) C52 0.062(5) 0.071(5) 0.073(5) 0.002(4) 0.031(4) 0.005(4) O53 0.066(3) 0.186(7) 0.051(3) 0.000(4) 0.018(3) -0.055(4) C54 0.072(5) 0.128(8) 0.074(5) -0.023(5) 0.026(4) -0.042(6) O55 0.052(3) 0.086(4) 0.064(3) 0.014(3) 0.015(2) -0.001(3) C56 0.073(6) 0.091(7) 0.114(7) 0.015(5) 0.022(5) -0.024(5) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag Y O33 2.274(3) . ? Y O26 2.311(3) . ? Y O13 2.330(3) . ? Y O46 2.353(3) . ? Y N11 2.442(4) . ? Y N31 2.451(4) . ? Y N22 2.483(4) . ? Y N42 2.518(4) . ? N11 C20 1.328(6) . ? N11 C12 1.355(6) . ? C12 C17 1.418(7) . ? C12 C13 1.425(7) . ? C13 O13 1.320(6) . ? C13 C14 1.376(7) . ? C14 C15 1.406(8) . ? C15 C16 1.362(9) . ? C16 C17 1.412(8) . ? C17 C18 1.405(8) . ? C18 C19 1.358(8) . ? C19 C20 1.405(7) . ? C20 C21 1.455(7) . ? C21 N22 1.289(6) . ? N22 N23 1.361(6) . ? N23 C24 1.343(6) . ? C24 O26 1.266(6) . ? C24 N25 1.349(7) . ? N31 C40 1.335(6) . ? N31 C32 1.350(6) . ? C32 C37 1.414(7) . ? C32 C33 1.433(7) . ? C33 O33 1.330(6) . ? C33 C34 1.373(7) . ? C34 C35 1.421(8) . ? C35 C36 1.353(8) . ? C36 C37 1.420(8) . ? C37 C38 1.405(8) . ? C38 C39 1.369(8) . ? C39 C40 1.408(7) . ? C40 C41 1.466(7) . ? C41 N42 1.280(6) . ? N42 N43 1.356(6) . ? N43 C44 1.368(6) . ? C44 O46 1.251(6) . ? C44 N45 1.329(7) . ? O51 C52 1.401(8) . ? O53 C54 1.360(8) . ? O55 C56 1.411(8) . ? O61 C64 1.354(12) . ? O61 C62 1.366(11) . ? C62 C63 1.332(15) . ? C64 C65 1.329(15) . ? 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 O33 Y O26 93.65(13) . . ? O33 Y O13 95.21(12) . . ? O26 Y O13 163.46(12) . . ? O33 Y O46 165.90(11) . . ? O26 Y O46 87.82(12) . . ? O13 Y O46 86.98(12) . . ? O33 Y N11 86.13(13) . . ? O26 Y N11 127.49(12) . . ? O13 Y N11 67.15(12) . . ? O46 Y N11 81.89(12) . . ? O33 Y N31 67.62(12) . . ? O26 Y N31 86.25(12) . . ? O13 Y N31 84.26(12) . . ? O46 Y N31 126.48(12) . . ? N11 Y N31 139.32(13) . . ? O33 Y N22 82.96(12) . . ? O26 Y N22 64.17(12) . . ? O13 Y N22 130.85(12) . . ? O46 Y N22 85.08(12) . . ? N11 Y N22 63.72(13) . . ? N31 Y N22 136.89(13) . . ? O33 Y N42 130.22(12) . . ? O26 Y N42 81.12(12) . . ? O13 Y N42 82.49(12) . . ? O46 Y N42 63.86(12) . . ? N11 Y N42 135.32(13) . . ? N31 Y N42 62.66(13) . . ? N22 Y N42 134.33(12) . . ? C20 N11 C12 120.2(4) . . ? C20 N11 Y 122.4(3) . . ? C12 N11 Y 117.4(3) . . ? N11 C12 C17 121.9(4) . . ? N11 C12 C13 115.8(4) . . ? C17 C12 C13 122.3(5) . . ? O13 C13 C14 124.8(5) . . ? O13 C13 C12 118.3(4) . . ? C14 C13 C12 116.8(5) . . ? C13 O13 Y 121.4(3) . . ? C13 C14 C15 120.9(5) . . ? C16 C15 C14 122.8(5) . . ? C15 C16 C17 118.8(5) . . ? C18 C17 C16 125.5(5) . . ? C18 C17 C12 116.1(5) . . ? C16 C17 C12 118.3(5) . . ? C19 C18 C17 121.4(5) . . ? C18 C19 C20 119.1(5) . . ? N11 C20 C19 121.3(5) . . ? N11 C20 C21 115.4(4) . . ? C19 C20 C21 123.3(5) . . ? N22 C21 C20 116.4(4) . . ? C21 N22 N23 118.8(4) . . ? C21 N22 Y 121.9(3) . . ? N23 N22 Y 119.2(3) . . ? C24 N23 N22 109.2(4) . . ? O26 C24 N23 126.1(5) . . ? O26 C24 N25 118.9(5) . . ? N23 C24 N25 114.9(5) . . ? C24 O26 Y 120.4(3) . . ? C40 N31 C32 119.5(4) . . ? C40 N31 Y 123.9(3) . . ? C32 N31 Y 116.7(3) . . ? N31 C32 C37 122.4(5) . . ? N31 C32 C33 115.4(4) . . ? C37 C32 C33 122.2(5) . . ? O33 C33 C34 125.2(5) . . ? O33 C33 C32 117.8(4) . . ? C34 C33 C32 117.0(5) . . ? C33 O33 Y 122.5(3) . . ? C33 C34 C35 120.7(5) . . ? C36 C35 C34 122.6(5) . . ? C35 C36 C37 119.2(5) . . ? C38 C37 C32 116.5(5) . . ? C38 C37 C36 125.2(5) . . ? C32 C37 C36 118.3(5) . . ? C39 C38 C37 121.3(5) . . ? C38 C39 C40 118.2(5) . . ? N31 C40 C39 122.2(5) . . ? N31 C40 C41 114.7(4) . . ? C39 C40 C41 123.1(5) . . ? N42 C41 C40 115.9(4) . . ? C41 N42 N43 120.1(4) . . ? C41 N42 Y 122.8(3) . . ? N43 N42 Y 117.0(3) . . ? N42 N43 C44 114.1(4) . . ? O46 C44 N45 122.3(5) . . ? O46 C44 N43 121.5(4) . . ? N45 C44 N43 116.3(5) . . ? C44 O46 Y 123.4(3) . . ? C64 O61 C62 133.7(15) . . ? C63 C62 O61 128.0(13) . . ? C65 C64 O61 128.9(15) . . ? 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 O33 Y N11 C20 81.8(4) . . . . ? O26 Y N11 C20 -9.8(4) . . . . ? O13 Y N11 C20 179.1(4) . . . . ? O46 Y N11 C20 -90.7(4) . . . . ? N31 Y N11 C20 130.2(4) . . . . ? N22 Y N11 C20 -2.2(3) . . . . ? N42 Y N11 C20 -129.8(4) . . . . ? O33 Y N11 C12 -97.2(3) . . . . ? O26 Y N11 C12 171.2(3) . . . . ? O13 Y N11 C12 0.1(3) . . . . ? O46 Y N11 C12 90.3(3) . . . . ? N31 Y N11 C12 -48.8(4) . . . . ? N22 Y N11 C12 178.8(4) . . . . ? N42 Y N11 C12 51.2(4) . . . . ? C20 N11 C12 C17 1.5(7) . . . . ? Y N11 C12 C17 -179.5(4) . . . . ? C20 N11 C12 C13 -178.2(4) . . . . ? Y N11 C12 C13 0.8(6) . . . . ? N11 C12 C13 O13 -1.9(7) . . . . ? C17 C12 C13 O13 178.4(5) . . . . ? N11 C12 C13 C14 178.7(5) . . . . ? C17 C12 C13 C14 -1.0(8) . . . . ? C14 C13 O13 Y -178.5(4) . . . . ? C12 C13 O13 Y 2.2(6) . . . . ? O33 Y O13 C13 82.3(3) . . . . ? O26 Y O13 C13 -155.5(4) . . . . ? O46 Y O13 C13 -83.7(3) . . . . ? N11 Y O13 C13 -1.2(3) . . . . ? N31 Y O13 C13 149.2(4) . . . . ? N22 Y O13 C13 -2.8(4) . . . . ? N42 Y O13 C13 -147.7(4) . . . . ? O13 C13 C14 C15 -177.9(5) . . . . ? C12 C13 C14 C15 1.4(8) . . . . ? C13 C14 C15 C16 -1.3(10) . . . . ? C14 C15 C16 C17 0.7(10) . . . . ? C15 C16 C17 C18 -178.8(6) . . . . ? C15 C16 C17 C12 -0.3(9) . . . . ? N11 C12 C17 C18 -0.6(8) . . . . ? C13 C12 C17 C18 179.1(5) . . . . ? N11 C12 C17 C16 -179.2(5) . . . . ? C13 C12 C17 C16 0.4(8) . . . . ? C16 C17 C18 C19 178.1(6) . . . . ? C12 C17 C18 C19 -0.5(9) . . . . ? C17 C18 C19 C20 0.6(9) . . . . ? C12 N11 C20 C19 -1.4(7) . . . . ? Y N11 C20 C19 179.7(4) . . . . ? C12 N11 C20 C21 -179.6(4) . . . . ? Y N11 C20 C21 1.5(6) . . . . ? C18 C19 C20 N11 0.3(8) . . . . ? C18 C19 C20 C21 178.3(5) . . . . ? N11 C20 C21 N22 1.4(7) . . . . ? C19 C20 C21 N22 -176.8(5) . . . . ? C20 C21 N22 N23 179.5(4) . . . . ? C20 C21 N22 Y -3.6(6) . . . . ? O33 Y N22 C21 -86.1(4) . . . . ? O26 Y N22 C21 176.4(4) . . . . ? O13 Y N22 C21 4.7(5) . . . . ? O46 Y N22 C21 86.4(4) . . . . ? N11 Y N22 C21 3.1(4) . . . . ? N31 Y N22 C21 -132.2(4) . . . . ? N42 Y N22 C21 131.8(4) . . . . ? O33 Y N22 N23 90.9(3) . . . . ? O26 Y N22 N23 -6.6(3) . . . . ? O13 Y N22 N23 -178.3(3) . . . . ? O46 Y N22 N23 -96.6(3) . . . . ? N11 Y N22 N23 -180.0(4) . . . . ? N31 Y N22 N23 44.8(4) . . . . ? N42 Y N22 N23 -51.2(4) . . . . ? C21 N22 N23 C24 -178.4(5) . . . . ? Y N22 N23 C24 4.5(5) . . . . ? N22 N23 C24 O26 3.3(7) . . . . ? N22 N23 C24 N25 -177.0(5) . . . . ? N23 C24 O26 Y -10.2(7) . . . . ? N25 C24 O26 Y 170.2(4) . . . . ? O33 Y O26 C24 -72.2(4) . . . . ? O13 Y O26 C24 165.4(4) . . . . ? O46 Y O26 C24 93.7(4) . . . . ? N11 Y O26 C24 15.7(4) . . . . ? N31 Y O26 C24 -139.5(4) . . . . ? N22 Y O26 C24 8.1(4) . . . . ? N42 Y O26 C24 157.6(4) . . . . ? O33 Y N31 C40 -178.9(4) . . . . ? O26 Y N31 C40 -83.4(4) . . . . ? O13 Y N31 C40 83.0(4) . . . . ? O46 Y N31 C40 1.1(4) . . . . ? N11 Y N31 C40 127.3(4) . . . . ? N22 Y N31 C40 -128.3(4) . . . . ? N42 Y N31 C40 -1.5(3) . . . . ? O33 Y N31 C32 1.3(3) . . . . ? O26 Y N31 C32 96.8(3) . . . . ? O13 Y N31 C32 -96.8(3) . . . . ? O46 Y N31 C32 -178.7(3) . . . . ? N11 Y N31 C32 -52.5(4) . . . . ? N22 Y N31 C32 51.9(4) . . . . ? N42 Y N31 C32 178.7(4) . . . . ? C40 N31 C32 C37 -0.4(7) . . . . ? Y N31 C32 C37 179.4(4) . . . . ? C40 N31 C32 C33 178.4(4) . . . . ? Y N31 C32 C33 -1.8(5) . . . . ? N31 C32 C33 O33 1.3(7) . . . . ? C37 C32 C33 O33 -179.9(4) . . . . ? N31 C32 C33 C34 -178.2(4) . . . . ? C37 C32 C33 C34 0.6(7) . . . . ? C34 C33 O33 Y 179.4(4) . . . . ? C32 C33 O33 Y -0.1(6) . . . . ? O26 Y O33 C33 -85.0(4) . . . . ? O13 Y O33 C33 81.0(4) . . . . ? O46 Y O33 C33 179.4(4) . . . . ? N11 Y O33 C33 147.6(4) . . . . ? N31 Y O33 C33 -0.6(3) . . . . ? N22 Y O33 C33 -148.4(4) . . . . ? N42 Y O33 C33 -3.6(4) . . . . ? O33 C33 C34 C35 180.0(5) . . . . ? C32 C33 C34 C35 -0.5(8) . . . . ? C33 C34 C35 C36 0.6(9) . . . . ? C34 C35 C36 C37 -0.7(9) . . . . ? N31 C32 C37 C38 -0.5(7) . . . . ? C33 C32 C37 C38 -179.2(5) . . . . ? N31 C32 C37 C36 178.0(5) . . . . ? C33 C32 C37 C36 -0.7(7) . . . . ? C35 C36 C37 C38 179.1(5) . . . . ? C35 C36 C37 C32 0.8(8) . . . . ? C32 C37 C38 C39 0.1(8) . . . . ? C36 C37 C38 C39 -178.3(5) . . . . ? C37 C38 C39 C40 1.1(8) . . . . ? C32 N31 C40 C39 1.7(7) . . . . ? Y N31 C40 C39 -178.1(4) . . . . ? C32 N31 C40 C41 -178.8(4) . . . . ? Y N31 C40 C41 1.4(6) . . . . ? C38 C39 C40 N31 -2.0(8) . . . . ? C38 C39 C40 C41 178.5(5) . . . . ? N31 C40 C41 N42 0.1(6) . . . . ? C39 C40 C41 N42 179.6(5) . . . . ? C40 C41 N42 N43 179.4(4) . . . . ? C40 C41 N42 Y -1.5(6) . . . . ? O33 Y N42 C41 4.7(4) . . . . ? O26 Y N42 C41 91.9(4) . . . . ? O13 Y N42 C41 -85.8(4) . . . . ? O46 Y N42 C41 -176.2(4) . . . . ? N11 Y N42 C41 -132.2(4) . . . . ? N31 Y N42 C41 1.6(3) . . . . ? N22 Y N42 C41 131.6(3) . . . . ? O33 Y N42 N43 -176.2(3) . . . . ? O26 Y N42 N43 -88.9(3) . . . . ? O13 Y N42 N43 93.3(3) . . . . ? O46 Y N42 N43 3.0(3) . . . . ? N11 Y N42 N43 47.0(4) . . . . ? N31 Y N42 N43 -179.3(3) . . . . ? N22 Y N42 N43 -49.2(4) . . . . ? C41 N42 N43 C44 176.3(4) . . . . ? Y N42 N43 C44 -2.9(5) . . . . ? N42 N43 C44 O46 0.3(6) . . . . ? N42 N43 C44 N45 -179.3(4) . . . . ? N45 C44 O46 Y -177.6(3) . . . . ? N43 C44 O46 Y 2.9(6) . . . . ? O33 Y O46 C44 174.4(5) . . . . ? O26 Y O46 C44 78.1(4) . . . . ? O13 Y O46 C44 -86.2(3) . . . . ? N11 Y O46 C44 -153.5(4) . . . . ? N31 Y O46 C44 -5.6(4) . . . . ? N22 Y O46 C44 142.4(4) . . . . ? N42 Y O46 C44 -3.1(3) . . . . ? C64 O61 C62 C63 170(2) . . . . ? C62 O61 C64 C65 -169.8(19) . . . . ? _diffrn_measured_fraction_theta_max 0.998 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 0.998 _refine_diff_density_max 1.400 _refine_diff_density_min -0.776 _refine_diff_density_rms 0.088 data_fro3205 _database_code_depnum_ccdc_archive 'CCDC 273600' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C26 H34 La2 N12 O20' _chemical_formula_weight 1112.47 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 monoclinic _symmetry_space_group_name_H-M P21/n 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 11.702(1) _cell_length_b 13.526(1) _cell_length_c 12.495(1) _cell_angle_alpha 90.00 _cell_angle_beta 108.70(1) _cell_angle_gamma 90.00 _cell_volume 1873.3(3) _cell_formula_units_Z 2 _cell_measurement_temperature 198(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description needle _exptl_crystal_colour orange _exptl_crystal_size_max 0.35 _exptl_crystal_size_mid 0.06 _exptl_crystal_size_min 0.06 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.972 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1096 _exptl_absorpt_coefficient_mu 2.349 _exptl_absorpt_correction_type empirical _exptl_absorpt_correction_T_min 0.4935 _exptl_absorpt_correction_T_max 0.8719 _exptl_absorpt_process_details 'SORTAV (Blessing, 1995 & 1997)' _exptl_special_details ; ? ; _diffrn_ambient_temperature 198(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'rotating anode Nonius FR591' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Nonius KappaCCD' _diffrn_measurement_method '\w and \f scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 17418 _diffrn_reflns_av_R_equivalents 0.0441 _diffrn_reflns_av_sigmaI/netI 0.0328 _diffrn_reflns_limit_h_min -14 _diffrn_reflns_limit_h_max 15 _diffrn_reflns_limit_k_min -15 _diffrn_reflns_limit_k_max 17 _diffrn_reflns_limit_l_min -12 _diffrn_reflns_limit_l_max 16 _diffrn_reflns_theta_min 2.56 _diffrn_reflns_theta_max 27.92 _reflns_number_total 4476 _reflns_number_gt 3867 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Collect (Nonius B.V., 1998)' _computing_cell_refinement 'Collect (Nonius B.V., 1998)' _computing_data_reduction 'Denzo-SMN (Otwinowski & Minor, 1997)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'SCHAKAL (Keller, 1997)' _computing_publication_material '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^)+(0.0494P)^2^+4.3856P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens 'at N from difmap. other geom' _refine_ls_hydrogen_treatment mixed _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 4476 _refine_ls_number_parameters 273 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0493 _refine_ls_R_factor_gt 0.0399 _refine_ls_wR_factor_ref 0.1028 _refine_ls_wR_factor_gt 0.0985 _refine_ls_goodness_of_fit_ref 1.064 _refine_ls_restrained_S_all 1.064 _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 La La 0.52986(2) 0.089229(16) 0.132806(19) 0.03051(9) Uani 1 1 d . . . N11 N 0.4280(4) -0.0164(3) 0.2440(3) 0.0463(9) Uani 1 1 d . . . C12 C 0.4212(5) -0.1147(4) 0.2211(4) 0.0467(11) Uani 1 1 d . . . C13 C 0.4515(4) -0.1461(4) 0.1251(4) 0.0448(11) Uani 1 1 d . . . O13 O 0.4812(3) -0.0774(2) 0.0609(3) 0.0457(8) Uani 1 1 d . . . C14 C 0.4474(5) -0.2460(4) 0.1033(5) 0.0530(12) Uani 1 1 d . . . H14 H 0.4691 -0.2697 0.0408 0.064 Uiso 1 1 calc R . . C15 C 0.4111(5) -0.3144(4) 0.1727(5) 0.0591(14) Uani 1 1 d . . . H15 H 0.4084 -0.3828 0.1544 0.071 Uiso 1 1 calc R . . C16 C 0.3807(5) -0.2864(4) 0.2630(5) 0.0616(15) Uani 1 1 d . . . H16 H 0.3578 -0.3340 0.3081 0.074 Uiso 1 1 calc R . . C17 C 0.3833(5) -0.1828(4) 0.2903(5) 0.0551(13) Uani 1 1 d . . . C18 C 0.3510(6) -0.1437(5) 0.3803(5) 0.0657(16) Uani 1 1 d . . . H18 H 0.3263 -0.1870 0.4286 0.079 Uiso 1 1 calc R . . C19 C 0.3544(6) -0.0462(5) 0.3993(5) 0.0641(15) Uani 1 1 d . . . H19 H 0.3305 -0.0203 0.4596 0.077 Uiso 1 1 calc R . . C20 C 0.3939(5) 0.0179(4) 0.3289(4) 0.0529(12) Uani 1 1 d . . . C21 C 0.3998(5) 0.1240(5) 0.3449(5) 0.0534(12) Uani 1 1 d . . . H21 H 0.3764 0.1551 0.4028 0.064 Uiso 1 1 calc R . . N22 N 0.4387(4) 0.1735(3) 0.2761(4) 0.0494(10) Uani 1 1 d . . . N23 N 0.4448(4) 0.2749(3) 0.2837(4) 0.0562(11) Uani 1 1 d . . . H23 H 0.3965 0.3110 0.3299 0.067 Uiso 1 1 d R . . C24 C 0.4920(5) 0.3193(4) 0.2089(5) 0.0513(12) Uani 1 1 d . . . N25 N 0.5017(5) 0.4165(3) 0.2151(5) 0.0635(13) Uani 1 1 d . . . H25A H 0.4935 0.4563 0.2888 0.095 Uiso 1 1 d R . . H25B H 0.5378 0.4566 0.1531 0.095 Uiso 1 1 d R . . O26 O 0.5216(3) 0.2674(3) 0.1392(3) 0.0521(9) Uani 1 1 d . . . N31 N 0.7390(4) 0.0345(3) 0.3277(4) 0.0512(10) Uani 1 1 d . . . O32 O 0.6733(4) 0.1058(3) 0.3338(3) 0.0593(10) Uani 1 1 d . . . O33 O 0.7007(4) -0.0207(3) 0.2412(3) 0.0567(9) Uani 1 1 d . . . O34 O 0.8359(4) 0.0185(4) 0.4018(4) 0.0812(14) Uani 1 1 d . . . O41 O 0.7228(3) 0.1552(3) 0.1247(3) 0.0572(9) Uani 1 1 d . . . H41 H 0.7657 0.1159 0.1021 0.086 Uiso 1 1 d R . . C42 C 0.7812(6) 0.2498(5) 0.1473(6) 0.0699(17) Uani 1 1 d . . . H42A H 0.7363 0.2975 0.0903 0.105 Uiso 1 1 calc R . . H42B H 0.8637 0.2440 0.1446 0.105 Uiso 1 1 calc R . . H42C H 0.7835 0.2725 0.2224 0.105 Uiso 1 1 calc R . . O51 O 0.3182(4) 0.1194(3) 0.0380(3) 0.0627(10) Uani 1 1 d . . . H51 H 0.2771 0.0672 0.0268 0.094 Uiso 1 1 d R . . C52 C 0.2670(6) 0.1877(5) -0.0552(5) 0.0740(19) Uani 1 1 d . . . H52A H 0.3056 0.2525 -0.0361 0.111 Uiso 1 1 calc R . . H52B H 0.1801 0.1943 -0.0686 0.111 Uiso 1 1 calc R . . H52C H 0.2807 0.1623 -0.1235 0.111 Uiso 1 1 calc R . . N61 N 0.3673(3) 0.4323(2) 0.4546(3) 0.0290(7) Uani 1 1 d . . . O62 O 0.4046(6) 0.3458(4) 0.4721(5) 0.1026(18) Uani 1 1 d . . . O63 O 0.3355(5) 0.4732(4) 0.5324(5) 0.0913(15) Uani 1 1 d . . . O64 O 0.3774(5) 0.4806(4) 0.3793(5) 0.0944(16) 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 La 0.02986(14) 0.02686(13) 0.03097(14) 0.00152(9) 0.00438(9) -0.00266(9) N11 0.043(2) 0.048(2) 0.045(2) 0.0042(18) 0.0095(18) -0.0017(18) C12 0.043(3) 0.046(3) 0.045(3) 0.007(2) 0.006(2) -0.007(2) C13 0.045(3) 0.041(3) 0.041(2) 0.0093(19) 0.003(2) -0.006(2) O13 0.055(2) 0.0356(17) 0.0434(18) 0.0045(13) 0.0112(15) -0.0081(14) C14 0.056(3) 0.041(3) 0.055(3) 0.007(2) 0.008(2) -0.006(2) C15 0.065(4) 0.044(3) 0.059(3) 0.012(2) 0.007(3) -0.008(3) C16 0.063(3) 0.053(3) 0.061(3) 0.019(3) 0.009(3) -0.016(3) C17 0.048(3) 0.059(3) 0.053(3) 0.015(3) 0.010(2) -0.012(2) C18 0.065(4) 0.071(4) 0.064(4) 0.018(3) 0.024(3) -0.011(3) C19 0.065(4) 0.079(4) 0.052(3) 0.008(3) 0.025(3) -0.007(3) C20 0.048(3) 0.064(3) 0.048(3) 0.003(2) 0.016(2) -0.002(2) C21 0.049(3) 0.064(3) 0.046(3) 0.002(2) 0.015(2) 0.002(3) N22 0.043(2) 0.048(2) 0.052(2) 0.0006(19) 0.0081(19) 0.0007(18) N23 0.056(3) 0.049(2) 0.061(3) -0.004(2) 0.015(2) 0.004(2) C24 0.044(3) 0.048(3) 0.056(3) -0.001(2) 0.008(2) 0.000(2) N25 0.068(3) 0.043(3) 0.073(3) -0.002(2) 0.014(3) 0.004(2) O26 0.056(2) 0.0440(19) 0.055(2) -0.0041(16) 0.0157(17) -0.0014(16) N31 0.047(2) 0.052(3) 0.046(2) 0.0006(19) 0.0031(19) 0.006(2) O32 0.054(2) 0.063(2) 0.053(2) -0.0118(18) 0.0063(18) 0.0124(18) O33 0.062(2) 0.0435(19) 0.053(2) -0.0043(16) 0.0031(18) 0.0025(17) O34 0.066(3) 0.097(4) 0.060(3) -0.005(2) -0.009(2) 0.023(2) O41 0.049(2) 0.051(2) 0.067(2) 0.0051(18) 0.0120(18) -0.0067(16) C42 0.057(3) 0.066(4) 0.078(4) -0.013(3) 0.009(3) -0.024(3) O51 0.048(2) 0.069(3) 0.061(2) 0.007(2) 0.0027(18) 0.0017(19) C52 0.071(4) 0.084(5) 0.054(3) -0.003(3) 0.002(3) 0.031(4) N61 0.0317(17) 0.0203(15) 0.0403(18) -0.0057(13) 0.0187(15) 0.0044(12) O62 0.143(5) 0.074(3) 0.094(4) 0.001(3) 0.044(4) 0.025(3) O63 0.095(4) 0.076(3) 0.110(4) -0.005(3) 0.043(3) 0.009(3) O64 0.101(4) 0.077(3) 0.112(4) -0.005(3) 0.044(3) 0.005(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 La O13 2.387(3) 3_655 ? La O51 2.413(4) . ? La O26 2.414(4) . ? La O13 2.425(3) . ? La O41 2.460(4) . ? La O33 2.512(4) . ? La N11 2.541(4) . ? La O32 2.545(4) . ? La N22 2.620(5) . ? La N31 2.940(4) . ? La La 3.9802(5) 3_655 ? N11 C20 1.331(7) . ? N11 C12 1.356(7) . ? C12 C13 1.421(7) . ? C12 C17 1.428(7) . ? C13 O13 1.345(6) . ? C13 C14 1.376(7) . ? O13 La 2.387(3) 3_655 ? C14 C15 1.423(7) . ? C15 C16 1.342(9) . ? C16 C17 1.439(8) . ? C17 C18 1.400(9) . ? C18 C19 1.339(10) . ? C19 C20 1.414(8) . ? C20 C21 1.448(8) . ? C21 N22 1.283(7) . ? N22 N23 1.375(6) . ? N23 C24 1.367(7) . ? C24 O26 1.252(6) . ? C24 N25 1.319(7) . ? N31 O34 1.232(5) . ? N31 O32 1.251(6) . ? N31 O33 1.271(5) . ? O41 C42 1.435(7) . ? O51 C52 1.456(7) . ? N61 O64 1.182(6) . ? N61 O62 1.244(6) . ? N61 O63 1.273(6) . ? 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 O13 La O51 78.48(14) 3_655 . ? O13 La O26 96.36(11) 3_655 . ? O51 La O26 78.56(13) . . ? O13 La O13 68.40(12) 3_655 . ? O51 La O13 83.88(14) . . ? O26 La O13 158.85(11) . . ? O13 La O41 74.62(12) 3_655 . ? O51 La O41 136.84(14) . . ? O26 La O41 71.69(13) . . ? O13 La O41 115.56(13) . . ? O13 La O33 106.39(12) 3_655 . ? O51 La O33 151.55(14) . . ? O26 La O33 127.34(12) . . ? O13 La O33 72.62(12) . . ? O41 La O33 69.81(13) . . ? O13 La N11 129.35(12) 3_655 . ? O51 La N11 77.04(14) . . ? O26 La N11 120.85(13) . . ? O13 La N11 65.45(13) . . ? O41 La N11 145.54(13) . . ? O33 La N11 78.69(13) . . ? O13 La O32 144.19(13) 3_655 . ? O51 La O32 135.90(14) . . ? O26 La O32 84.27(12) . . ? O13 La O32 116.74(12) . . ? O41 La O32 71.64(13) . . ? O33 La O32 50.25(12) . . ? N11 La O32 77.68(14) . . ? O13 La N22 145.11(13) 3_655 . ? O51 La N22 71.52(14) . . ? O26 La N22 60.92(13) . . ? O13 La N22 123.97(13) . . ? O41 La N22 116.77(13) . . ? O33 La N22 108.48(13) . . ? N11 La N22 60.39(14) . . ? O32 La N22 64.62(13) . . ? O13 La N31 125.66(13) 3_655 . ? O51 La N31 154.13(14) . . ? O26 La N31 104.80(12) . . ? O13 La N31 96.15(12) . . ? O41 La N31 66.08(13) . . ? O33 La N31 25.44(11) . . ? N11 La N31 79.48(13) . . ? O32 La N31 25.05(12) . . ? N22 La N31 87.51(13) . . ? O13 La La 34.50(7) 3_655 3_655 ? O51 La La 79.35(11) . 3_655 ? O26 La La 129.39(8) . 3_655 ? O13 La La 33.89(8) . 3_655 ? O41 La La 95.95(10) . 3_655 ? O33 La La 89.27(8) . 3_655 ? N11 La La 97.30(10) . 3_655 ? O32 La La 139.51(8) . 3_655 ? N22 La La 146.34(9) . 3_655 ? N31 La La 114.52(9) . 3_655 ? C20 N11 C12 119.8(5) . . ? C20 N11 La 123.6(4) . . ? C12 N11 La 116.2(3) . . ? N11 C12 C13 117.2(4) . . ? N11 C12 C17 120.9(5) . . ? C13 C12 C17 121.9(5) . . ? O13 C13 C14 124.1(5) . . ? O13 C13 C12 118.6(4) . . ? C14 C13 C12 117.3(5) . . ? C13 O13 La 128.2(3) . 3_655 ? C13 O13 La 119.8(3) . . ? La O13 La 111.60(12) 3_655 . ? C13 C14 C15 121.1(6) . . ? C16 C15 C14 122.7(5) . . ? C15 C16 C17 118.9(5) . . ? C18 C17 C12 117.3(5) . . ? C18 C17 C16 124.6(5) . . ? C12 C17 C16 118.1(5) . . ? C19 C18 C17 121.0(5) . . ? C18 C19 C20 119.4(6) . . ? N11 C20 C19 121.6(6) . . ? N11 C20 C21 116.2(5) . . ? C19 C20 C21 122.2(5) . . ? N22 C21 C20 115.9(5) . . ? C21 N22 N23 119.7(5) . . ? C21 N22 La 122.8(4) . . ? N23 N22 La 117.2(3) . . ? C24 N23 N22 114.5(5) . . ? O26 C24 N25 124.2(6) . . ? O26 C24 N23 119.5(5) . . ? N25 C24 N23 116.3(5) . . ? C24 O26 La 127.3(3) . . ? O34 N31 O32 121.6(5) . . ? O34 N31 O33 121.6(5) . . ? O32 N31 O33 116.7(4) . . ? O34 N31 La 171.1(4) . . ? O32 N31 La 59.5(2) . . ? O33 N31 La 58.1(2) . . ? N31 O32 La 95.5(3) . . ? N31 O33 La 96.5(3) . . ? C42 O41 La 134.5(4) . . ? C52 O51 La 126.5(4) . . ? O64 N61 O62 122.7(5) . . ? O64 N61 O63 119.8(4) . . ? O62 N61 O63 116.5(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 O13 La N11 C20 -148.3(4) 3_655 . . . ? O51 La N11 C20 -85.3(4) . . . . ? O26 La N11 C20 -17.3(4) . . . . ? O13 La N11 C20 -174.4(4) . . . . ? O41 La N11 C20 85.6(5) . . . . ? O33 La N11 C20 109.7(4) . . . . ? O32 La N11 C20 58.3(4) . . . . ? N22 La N11 C20 -9.4(4) . . . . ? N31 La N11 C20 83.8(4) . . . . ? La La N11 C20 -162.5(4) 3_655 . . . ? O13 La N11 C12 38.9(4) 3_655 . . . ? O51 La N11 C12 101.9(4) . . . . ? O26 La N11 C12 169.9(3) . . . . ? O13 La N11 C12 12.8(3) . . . . ? O41 La N11 C12 -87.2(4) . . . . ? O33 La N11 C12 -63.1(3) . . . . ? O32 La N11 C12 -114.5(3) . . . . ? N22 La N11 C12 177.8(4) . . . . ? N31 La N11 C12 -89.0(3) . . . . ? La La N11 C12 24.6(3) 3_655 . . . ? C20 N11 C12 C13 176.1(5) . . . . ? La N11 C12 C13 -10.8(6) . . . . ? C20 N11 C12 C17 -3.0(7) . . . . ? La N11 C12 C17 170.1(4) . . . . ? N11 C12 C13 O13 -2.1(7) . . . . ? C17 C12 C13 O13 177.0(5) . . . . ? N11 C12 C13 C14 178.6(5) . . . . ? C17 C12 C13 C14 -2.4(7) . . . . ? C14 C13 O13 La 22.8(7) . . . 3_655 ? C12 C13 O13 La -156.5(3) . . . 3_655 ? C14 C13 O13 La -165.7(4) . . . . ? C12 C13 O13 La 15.0(6) . . . . ? O13 La O13 C13 -172.8(4) 3_655 . . . ? O51 La O13 C13 -92.8(3) . . . . ? O26 La O13 C13 -126.7(4) . . . . ? O41 La O13 C13 127.6(3) . . . . ? O33 La O13 C13 71.0(3) . . . . ? N11 La O13 C13 -14.3(3) . . . . ? O32 La O13 C13 46.2(4) . . . . ? N22 La O13 C13 -30.0(4) . . . . ? N31 La O13 C13 61.2(3) . . . . ? La La O13 C13 -172.8(4) 3_655 . . . ? O13 La O13 La 0.0 3_655 . . 3_655 ? O51 La O13 La 80.01(16) . . . 3_655 ? O26 La O13 La 46.1(4) . . . 3_655 ? O41 La O13 La -59.63(18) . . . 3_655 ? O33 La O13 La -116.23(17) . . . 3_655 ? N11 La O13 La 158.5(2) . . . 3_655 ? O32 La O13 La -141.00(15) . . . 3_655 ? N22 La O13 La 142.84(14) . . . 3_655 ? N31 La O13 La -126.02(15) . . . 3_655 ? O13 C13 C14 C15 -177.8(5) . . . . ? C12 C13 C14 C15 1.5(8) . . . . ? C13 C14 C15 C16 -0.8(9) . . . . ? C14 C15 C16 C17 0.8(9) . . . . ? N11 C12 C17 C18 1.4(8) . . . . ? C13 C12 C17 C18 -177.6(5) . . . . ? N11 C12 C17 C16 -178.6(5) . . . . ? C13 C12 C17 C16 2.4(8) . . . . ? C15 C16 C17 C18 178.4(6) . . . . ? C15 C16 C17 C12 -1.5(8) . . . . ? C12 C17 C18 C19 0.8(9) . . . . ? C16 C17 C18 C19 -179.2(6) . . . . ? C17 C18 C19 C20 -1.5(9) . . . . ? C12 N11 C20 C19 2.3(8) . . . . ? La N11 C20 C19 -170.3(4) . . . . ? C12 N11 C20 C21 -177.8(4) . . . . ? La N11 C20 C21 9.6(6) . . . . ? C18 C19 C20 N11 -0.1(9) . . . . ? C18 C19 C20 C21 -179.9(5) . . . . ? N11 C20 C21 N22 -0.8(7) . . . . ? C19 C20 C21 N22 179.1(5) . . . . ? C20 C21 N22 N23 178.6(4) . . . . ? C20 C21 N22 La -8.0(6) . . . . ? O13 La N22 C21 126.4(4) 3_655 . . . ? O51 La N22 C21 94.3(4) . . . . ? O26 La N22 C21 -178.8(4) . . . . ? O13 La N22 C21 25.4(5) . . . . ? O41 La N22 C21 -131.9(4) . . . . ? O33 La N22 C21 -55.7(4) . . . . ? N11 La N22 C21 9.0(4) . . . . ? O32 La N22 C21 -80.9(4) . . . . ? N31 La N22 C21 -70.3(4) . . . . ? La La N22 C21 62.9(5) 3_655 . . . ? O13 La N22 N23 -60.1(4) 3_655 . . . ? O51 La N22 N23 -92.2(4) . . . . ? O26 La N22 N23 -5.3(3) . . . . ? O13 La N22 N23 -161.1(3) . . . . ? O41 La N22 N23 41.6(4) . . . . ? O33 La N22 N23 117.8(3) . . . . ? N11 La N22 N23 -177.5(4) . . . . ? O32 La N22 N23 92.6(4) . . . . ? N31 La N22 N23 103.2(3) . . . . ? La La N22 N23 -123.6(3) 3_655 . . . ? C21 N22 N23 C24 177.6(5) . . . . ? La N22 N23 C24 3.9(6) . . . . ? N22 N23 C24 O26 2.2(7) . . . . ? N22 N23 C24 N25 -178.6(5) . . . . ? N25 C24 O26 La 172.4(4) . . . . ? N23 C24 O26 La -8.5(7) . . . . ? O13 La O26 C24 159.3(4) 3_655 . . . ? O51 La O26 C24 82.4(4) . . . . ? O13 La O26 C24 116.9(5) . . . . ? O41 La O26 C24 -129.3(4) . . . . ? O33 La O26 C24 -84.5(4) . . . . ? N11 La O26 C24 15.2(4) . . . . ? O32 La O26 C24 -56.8(4) . . . . ? N22 La O26 C24 7.3(4) . . . . ? N31 La O26 C24 -71.2(4) . . . . ? La La O26 C24 148.2(4) 3_655 . . . ? O13 La N31 O34 45(2) 3_655 . . . ? O51 La N31 O34 -158(2) . . . . ? O26 La N31 O34 -64(2) . . . . ? O13 La N31 O34 113(2) . . . . ? O41 La N31 O34 -2(2) . . . . ? O33 La N31 O34 91(2) . . . . ? N11 La N31 O34 177(2) . . . . ? O32 La N31 O34 -100(2) . . . . ? N22 La N31 O34 -123(2) . . . . ? La La N31 O34 83(2) 3_655 . . . ? O13 La N31 O32 145.3(3) 3_655 . . . ? O51 La N31 O32 -58.3(5) . . . . ? O26 La N31 O32 36.0(3) . . . . ? O13 La N31 O32 -147.0(3) . . . . ? O41 La N31 O32 97.8(3) . . . . ? O33 La N31 O32 -169.2(5) . . . . ? N11 La N31 O32 -83.4(3) . . . . ? N22 La N31 O32 -23.1(3) . . . . ? La La N31 O32 -176.7(3) 3_655 . . . ? O13 La N31 O33 -45.6(3) 3_655 . . . ? O51 La N31 O33 110.8(4) . . . . ? O26 La N31 O33 -154.9(3) . . . . ? O13 La N31 O33 22.2(3) . . . . ? O41 La N31 O33 -93.1(3) . . . . ? N11 La N31 O33 85.8(3) . . . . ? O32 La N31 O33 169.2(5) . . . . ? N22 La N31 O33 146.1(3) . . . . ? La La N31 O33 -7.5(3) 3_655 . . . ? O34 N31 O32 La 169.7(5) . . . . ? O33 N31 O32 La -10.3(5) . . . . ? O13 La O32 N31 -52.3(4) 3_655 . . . ? O51 La O32 N31 147.8(3) . . . . ? O26 La O32 N31 -145.2(3) . . . . ? O13 La O32 N31 37.4(4) . . . . ? O41 La O32 N31 -72.6(3) . . . . ? O33 La O32 N31 6.0(3) . . . . ? N11 La O32 N31 91.5(3) . . . . ? N22 La O32 N31 154.3(4) . . . . ? La La O32 N31 4.7(4) 3_655 . . . ? O34 N31 O33 La -169.6(5) . . . . ? O32 N31 O33 La 10.5(5) . . . . ? O13 La O33 N31 142.8(3) 3_655 . . . ? O51 La O33 N31 -121.1(3) . . . . ? O26 La O33 N31 31.1(4) . . . . ? O13 La O33 N31 -156.8(3) . . . . ? O41 La O33 N31 76.5(3) . . . . ? N11 La O33 N31 -89.2(3) . . . . ? O32 La O33 N31 -5.9(3) . . . . ? N22 La O33 N31 -36.0(3) . . . . ? La La O33 N31 173.2(3) 3_655 . . . ? O13 La O41 C42 117.1(5) 3_655 . . . ? O51 La O41 C42 63.7(6) . . . . ? O26 La O41 C42 14.9(5) . . . . ? O13 La O41 C42 173.4(5) . . . . ? O33 La O41 C42 -128.5(5) . . . . ? N11 La O41 C42 -103.3(5) . . . . ? O32 La O41 C42 -75.1(5) . . . . ? N22 La O41 C42 -27.4(5) . . . . ? N31 La O41 C42 -101.3(5) . . . . ? La La O41 C42 144.5(5) 3_655 . . . ? O13 La O51 C52 -48.3(4) 3_655 . . . ? O26 La O51 C52 50.7(4) . . . . ? O13 La O51 C52 -117.5(5) . . . . ? O41 La O51 C52 3.8(6) . . . . ? O33 La O51 C52 -151.5(4) . . . . ? N11 La O51 C52 176.4(5) . . . . ? O32 La O51 C52 119.9(4) . . . . ? N22 La O51 C52 113.6(5) . . . . ? N31 La O51 C52 151.0(4) . . . . ? La La O51 C52 -83.5(4) 3_655 . . . ? _diffrn_measured_fraction_theta_max 0.996 _diffrn_reflns_theta_full 27.92 _diffrn_measured_fraction_theta_full 0.996 _refine_diff_density_max 0.481 _refine_diff_density_min -1.096 _refine_diff_density_rms 0.119 data_fro3118 _database_code_depnum_ccdc_archive 'CCDC 273601' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C40 H60 Cl2 N16 O16 Y2' _chemical_formula_weight 1269.76 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' Y Y -2.7962 3.5667 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Cl Cl 0.1484 0.1585 '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 10.285(1) _cell_length_b 11.109(1) _cell_length_c 13.741(1) _cell_angle_alpha 68.92(1) _cell_angle_beta 68.11(1) _cell_angle_gamma 81.10(1) _cell_volume 1358.9(2) _cell_formula_units_Z 1 _cell_measurement_temperature 198(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description plate _exptl_crystal_colour yellow-red _exptl_crystal_size_max 0.25 _exptl_crystal_size_mid 0.20 _exptl_crystal_size_min 0.05 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.552 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 652 _exptl_absorpt_coefficient_mu 2.302 _exptl_absorpt_correction_type empirical _exptl_absorpt_correction_T_min 0.5968 _exptl_absorpt_correction_T_max 0.8936 _exptl_absorpt_process_details 'SORTAV (Blessing, 1995 & 1997)' _exptl_special_details ; ? ; _diffrn_ambient_temperature 198(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'rotating anode Nonius FR591' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Nonis KappaCCD' _diffrn_measurement_method '\w and \f scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 14430 _diffrn_reflns_av_R_equivalents 0.0556 _diffrn_reflns_av_sigmaI/netI 0.0549 _diffrn_reflns_limit_h_min -13 _diffrn_reflns_limit_h_max 13 _diffrn_reflns_limit_k_min -14 _diffrn_reflns_limit_k_max 14 _diffrn_reflns_limit_l_min -16 _diffrn_reflns_limit_l_max 18 _diffrn_reflns_theta_min 2.13 _diffrn_reflns_theta_max 27.91 _reflns_number_total 6462 _reflns_number_gt 5479 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Collect (Nonius B.V., 1998)' _computing_cell_refinement 'Collect (Nonius B.V., 1998)' _computing_data_reduction 'Denzo-SMN (Otwinowski & Minor, 1997)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'SCHAKAL (Keller, 1997)' _computing_publication_material '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. Non-bonded DMF solvent molecule only refined with isotropic thermal displacement parameters. Remaining electron density close to the Cl-anion and/or the non-bonded solvent molecule. ; _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^)+(0.1149P)^2^+3.0314P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens 'at N from difmap, other geom' _refine_ls_hydrogen_treatment mixed _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 6462 _refine_ls_number_parameters 328 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0815 _refine_ls_R_factor_gt 0.0682 _refine_ls_wR_factor_ref 0.1934 _refine_ls_wR_factor_gt 0.1827 _refine_ls_goodness_of_fit_ref 1.042 _refine_ls_restrained_S_all 1.042 _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 Y Y 0.81998(4) 0.41771(3) 0.06245(3) 0.02542(15) Uani 1 1 d . . . N11 N 0.9132(4) 0.1940(3) 0.1144(3) 0.0264(7) Uani 1 1 d . . . C12 C 1.0444(4) 0.1726(4) 0.0484(4) 0.0267(8) Uani 1 1 d . . . C13 C 1.1200(4) 0.2839(4) -0.0320(4) 0.0278(8) Uani 1 1 d . . . O13 O 1.0614(3) 0.3993(3) -0.0304(3) 0.0286(6) Uani 1 1 d . . . C14 C 1.2500(5) 0.2641(4) -0.1042(4) 0.0352(10) Uani 1 1 d . . . H14 H 1.3005 0.3361 -0.1618 0.042 Uiso 1 1 calc R . . C15 C 1.3094(5) 0.1388(5) -0.0941(5) 0.0427(12) Uani 1 1 d . . . H15 H 1.3999 0.1284 -0.1444 0.051 Uiso 1 1 calc R . . C16 C 1.2402(5) 0.0326(4) -0.0139(5) 0.0406(11) Uani 1 1 d . . . H16 H 1.2824 -0.0508 -0.0083 0.049 Uiso 1 1 calc R . . C17 C 1.1054(5) 0.0471(4) 0.0607(4) 0.0342(10) Uani 1 1 d . . . C18 C 1.0246(6) -0.0559(4) 0.1482(4) 0.0402(11) Uani 1 1 d . . . H18 H 1.0611 -0.1419 0.1601 0.048 Uiso 1 1 calc R . . C19 C 0.8954(6) -0.0323(4) 0.2149(4) 0.0386(11) Uani 1 1 d . . . H19 H 0.8423 -0.1009 0.2751 0.046 Uiso 1 1 calc R . . C20 C 0.8407(5) 0.0948(4) 0.1944(4) 0.0292(9) Uani 1 1 d . . . C21 C 0.6991(5) 0.1264(4) 0.2595(4) 0.0301(9) Uani 1 1 d . . . H21 H 0.6404 0.0638 0.3224 0.036 Uiso 1 1 calc R . . N22 N 0.6602(4) 0.2441(3) 0.2256(3) 0.0300(8) Uani 1 1 d . . . N23 N 0.5314(4) 0.2856(4) 0.2802(4) 0.0365(9) Uani 1 1 d . . . H23 H 0.4697 0.2334 0.3378 0.044 Uiso 1 1 calc R . . C24 C 0.5054(5) 0.4151(4) 0.2386(4) 0.0345(10) Uani 1 1 d . . . N25 N 0.3827(5) 0.4579(5) 0.2941(5) 0.0490(12) Uani 1 1 d . . . H25A H 0.378(8) 0.527(8) 0.273(6) 0.059 Uiso 1 1 d . . . H25B H 0.338(7) 0.396(7) 0.351(6) 0.059 Uiso 1 1 d . . . O26 O 0.5930(3) 0.4852(3) 0.1544(3) 0.0397(8) Uani 1 1 d . . . O31 O 0.8335(4) 0.4008(3) 0.2337(3) 0.0422(8) Uani 1 1 d . . . C32 C 0.9012(6) 0.4535(5) 0.2643(4) 0.0392(11) Uani 1 1 d . . . H32 H 1.0004 0.4535 0.2308 0.047 Uiso 1 1 calc R . . N33 N 0.8443(6) 0.5096(5) 0.3403(4) 0.0490(11) Uani 1 1 d . . . C34 C 0.9292(11) 0.5728(9) 0.3716(8) 0.083(3) Uani 1 1 d . . . H34A H 1.0287 0.5564 0.3348 0.125 Uiso 1 1 calc R . . H34B H 0.9066 0.5386 0.4523 0.125 Uiso 1 1 calc R . . H34C H 0.9092 0.6660 0.3488 0.125 Uiso 1 1 calc R . . C35 C 0.6945(8) 0.5183(8) 0.3942(6) 0.070(2) Uani 1 1 d . . . H35A H 0.6474 0.4690 0.3709 0.106 Uiso 1 1 calc R . . H35B H 0.6630 0.6089 0.3734 0.106 Uiso 1 1 calc R . . H35C H 0.6713 0.4829 0.4750 0.106 Uiso 1 1 calc R . . O41 O 0.7698(3) 0.5875(3) -0.0815(3) 0.0357(7) Uani 1 1 d . . . C42 C 0.6816(5) 0.6767(4) -0.0813(5) 0.0377(11) Uani 1 1 d . . . H42 H 0.5954 0.6633 -0.0207 0.045 Uiso 1 1 calc R . . N43 N 0.7012(5) 0.7898(4) -0.1611(4) 0.0408(10) Uani 1 1 d . . . C44 C 0.5935(6) 0.8917(5) -0.1556(7) 0.0585(17) Uani 1 1 d . . . H44A H 0.5136 0.8613 -0.0867 0.088 Uiso 1 1 calc R . . H44B H 0.5625 0.9144 -0.2195 0.088 Uiso 1 1 calc R . . H44C H 0.6320 0.9678 -0.1568 0.088 Uiso 1 1 calc R . . C45 C 0.8301(7) 0.8194(6) -0.2536(5) 0.0541(15) Uani 1 1 d . . . H45A H 0.8989 0.7492 -0.2414 0.081 Uiso 1 1 calc R . . H45B H 0.8662 0.9000 -0.2609 0.081 Uiso 1 1 calc R . . H45C H 0.8133 0.8291 -0.3218 0.081 Uiso 1 1 calc R . . N51 N 0.7404(4) 0.3187(3) -0.0732(3) 0.0268(7) Uani 1 1 d . . . O52 O 0.8657(4) 0.3438(4) -0.1011(4) 0.0474(9) Uani 1 1 d . . . O53 O 0.6560(4) 0.3278(4) 0.0133(4) 0.0529(10) Uani 1 1 d . . . O54 O 0.7010(5) 0.2873(4) -0.1382(5) 0.0642(13) Uani 1 1 d . . . Cl Cl 0.2824(3) 0.1813(2) 0.49376(18) 0.0888(7) Uani 1 1 d . . . O71 O 0.6090(11) 0.2839(10) 0.6772(9) 0.141(3) Uiso 1 1 d . . . C72 C 0.7423(18) 0.2391(16) 0.6226(14) 0.152(5) Uiso 1 1 d . . . H72 H 0.8256 0.2536 0.6309 0.182 Uiso 1 1 calc R . . N73 N 0.7408(7) 0.1792(7) 0.5631(6) 0.0747(17) Uiso 1 1 d . . . C74 C 0.8392(16) 0.1270(15) 0.4847(13) 0.144(5) Uiso 1 1 d . . . H74A H 0.8388 0.1791 0.4101 0.216 Uiso 1 1 calc R . . H74B H 0.8146 0.0382 0.5014 0.216 Uiso 1 1 calc R . . H74C H 0.9328 0.1273 0.4878 0.216 Uiso 1 1 calc R . . C75 C 0.6006(17) 0.1640(17) 0.5577(15) 0.164(6) Uiso 1 1 d . . . H75A H 0.5255 0.1876 0.6175 0.246 Uiso 1 1 calc R . . H75B H 0.5906 0.0741 0.5662 0.246 Uiso 1 1 calc R . . H75C H 0.5947 0.2205 0.4858 0.246 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 Y 0.0233(2) 0.0153(2) 0.0328(2) -0.00572(15) -0.00734(15) 0.00197(13) N11 0.0287(17) 0.0170(15) 0.0301(18) -0.0066(14) -0.0088(14) 0.0024(13) C12 0.029(2) 0.0171(18) 0.033(2) -0.0102(16) -0.0094(17) 0.0030(15) C13 0.0266(19) 0.0167(18) 0.038(2) -0.0083(16) -0.0106(17) 0.0032(15) O13 0.0235(14) 0.0157(13) 0.0408(18) -0.0091(12) -0.0060(12) 0.0028(10) C14 0.033(2) 0.020(2) 0.043(3) -0.0095(18) -0.0043(19) 0.0043(16) C15 0.037(2) 0.030(2) 0.052(3) -0.017(2) -0.004(2) 0.0062(19) C16 0.042(3) 0.020(2) 0.048(3) -0.011(2) -0.007(2) 0.0086(18) C17 0.036(2) 0.020(2) 0.042(3) -0.0103(18) -0.012(2) 0.0081(17) C18 0.050(3) 0.0154(19) 0.042(3) -0.0071(18) -0.007(2) 0.0090(18) C19 0.047(3) 0.020(2) 0.037(3) -0.0044(18) -0.007(2) 0.0014(18) C20 0.035(2) 0.0199(19) 0.028(2) -0.0054(16) -0.0091(17) 0.0007(16) C21 0.033(2) 0.0201(19) 0.031(2) -0.0060(16) -0.0049(17) -0.0045(16) N22 0.0270(17) 0.0227(17) 0.034(2) -0.0087(15) -0.0051(15) 0.0000(13) N23 0.0282(18) 0.0238(18) 0.041(2) -0.0066(16) 0.0011(16) 0.0006(14) C24 0.028(2) 0.027(2) 0.038(3) -0.0078(19) -0.0046(18) 0.0030(17) N25 0.037(2) 0.028(2) 0.057(3) -0.009(2) 0.003(2) 0.0071(18) O26 0.0290(16) 0.0233(16) 0.049(2) -0.0063(14) -0.0003(14) 0.0028(12) O31 0.056(2) 0.0334(18) 0.0353(19) -0.0111(15) -0.0106(16) -0.0099(16) C32 0.048(3) 0.029(2) 0.037(3) -0.007(2) -0.015(2) 0.001(2) N33 0.072(3) 0.036(2) 0.043(3) -0.016(2) -0.024(2) 0.003(2) C34 0.121(7) 0.075(5) 0.083(6) -0.036(5) -0.056(6) -0.006(5) C35 0.076(5) 0.072(5) 0.055(4) -0.029(4) -0.013(3) 0.017(4) O41 0.0367(17) 0.0236(15) 0.0421(19) -0.0056(14) -0.0166(15) 0.0072(13) C42 0.032(2) 0.025(2) 0.051(3) -0.004(2) -0.017(2) 0.0007(17) N43 0.040(2) 0.026(2) 0.052(3) -0.0044(18) -0.020(2) 0.0042(16) C44 0.046(3) 0.027(3) 0.095(5) -0.007(3) -0.034(3) 0.011(2) C45 0.059(4) 0.041(3) 0.045(3) -0.001(2) -0.012(3) 0.001(3) N51 0.0307(18) 0.0104(14) 0.041(2) -0.0079(14) -0.0177(16) 0.0059(12) O52 0.042(2) 0.038(2) 0.064(3) -0.0196(18) -0.0200(18) 0.0051(16) O53 0.045(2) 0.052(2) 0.063(3) -0.013(2) -0.021(2) -0.0092(18) O54 0.083(3) 0.047(2) 0.087(3) -0.027(2) -0.057(3) 0.012(2) Cl 0.0994(15) 0.0683(12) 0.0607(11) -0.0150(9) 0.0153(10) -0.0206(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 Y O13 2.346(3) . ? Y O31 2.347(4) . ? Y O41 2.348(3) . ? Y O13 2.354(3) 2_765 ? Y O26 2.355(3) . ? Y N11 2.470(3) . ? Y O53 2.480(4) . ? Y O52 2.522(4) . ? Y N22 2.563(4) . ? Y N51 2.871(4) . ? Y Y 3.8858(9) 2_765 ? N11 C20 1.323(6) . ? N11 C12 1.358(5) . ? C12 C17 1.416(6) . ? C12 C13 1.424(6) . ? C13 O13 1.333(5) . ? C13 C14 1.377(6) . ? O13 Y 2.354(3) 2_765 ? C14 C15 1.411(6) . ? C15 C16 1.361(7) . ? C16 C17 1.410(7) . ? C17 C18 1.417(7) . ? C18 C19 1.353(7) . ? C19 C20 1.406(6) . ? C20 C21 1.463(6) . ? C21 N22 1.275(6) . ? N22 N23 1.361(5) . ? N23 C24 1.367(6) . ? C24 O26 1.245(6) . ? C24 N25 1.326(6) . ? O31 C32 1.236(6) . ? C32 N33 1.311(7) . ? N33 C35 1.445(9) . ? N33 C34 1.459(9) . ? O41 C42 1.236(6) . ? C42 N43 1.320(6) . ? N43 C45 1.436(8) . ? N43 C44 1.457(7) . ? N51 O53 1.211(6) . ? N51 O52 1.245(5) . ? N51 O54 1.273(6) . ? O71 C72 1.407(18) . ? C72 N73 1.231(17) . ? N73 C74 1.406(16) . ? N73 C75 1.509(16) . ? 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 O13 Y O31 97.00(13) . . ? O13 Y O41 97.38(11) . . ? O31 Y O41 134.32(12) . . ? O13 Y O13 68.46(12) . 2_765 ? O31 Y O13 73.62(12) . 2_765 ? O41 Y O13 71.98(11) . 2_765 ? O13 Y O26 165.79(11) . . ? O31 Y O26 77.92(14) . . ? O41 Y O26 77.66(12) . . ? O13 Y O26 97.34(11) 2_765 . ? O13 Y N11 66.77(11) . . ? O31 Y N11 80.80(13) . . ? O41 Y N11 144.28(12) . . ? O13 Y N11 124.37(11) 2_765 . ? O26 Y N11 124.52(12) . . ? O13 Y O53 118.38(14) . . ? O31 Y O53 132.34(14) . . ? O41 Y O53 74.72(13) . . ? O13 Y O53 146.64(13) 2_765 . ? O26 Y O53 73.52(15) . . ? N11 Y O53 84.95(13) . . ? O13 Y O52 69.09(12) . . ? O31 Y O52 154.53(13) . . ? O41 Y O52 70.25(12) . . ? O13 Y O52 117.33(12) 2_765 . ? O26 Y O52 120.36(13) . . ? N11 Y O52 74.14(12) . . ? O53 Y O52 50.43(14) . . ? O13 Y N22 127.46(11) . . ? O31 Y N22 67.46(12) . . ? O41 Y N22 130.11(12) . . ? O13 Y N22 139.11(12) 2_765 . ? O26 Y N22 63.13(12) . . ? N11 Y N22 61.40(12) . . ? O53 Y N22 65.77(14) . . ? O52 Y N22 103.33(13) . . ? O13 Y N51 94.41(11) . . ? O31 Y N51 151.31(11) . . ? O41 Y N51 69.48(11) . . ? O13 Y N51 135.04(11) 2_765 . ? O26 Y N51 96.22(12) . . ? N11 Y N51 79.70(10) . . ? O53 Y N51 24.81(13) . . ? O52 Y N51 25.67(12) . . ? N22 Y N51 84.73(12) . . ? O13 Y Y 34.29(7) . 2_765 ? O31 Y Y 84.42(9) . 2_765 ? O41 Y Y 83.69(8) . 2_765 ? O13 Y Y 34.16(7) 2_765 2_765 ? O26 Y Y 131.50(9) . 2_765 ? N11 Y Y 95.96(8) . 2_765 ? O53 Y Y 142.46(11) . 2_765 ? O52 Y Y 93.59(9) . 2_765 ? N22 Y Y 145.60(9) . 2_765 ? N51 Y Y 118.36(8) . 2_765 ? C20 N11 C12 119.1(4) . . ? C20 N11 Y 124.7(3) . . ? C12 N11 Y 115.9(3) . . ? N11 C12 C17 122.2(4) . . ? N11 C12 C13 116.4(3) . . ? C17 C12 C13 121.4(4) . . ? O13 C13 C14 124.9(4) . . ? O13 C13 C12 117.8(4) . . ? C14 C13 C12 117.4(4) . . ? C13 O13 Y 119.9(3) . . ? C13 O13 Y 125.8(3) . 2_765 ? Y O13 Y 111.54(12) . 2_765 ? C13 C14 C15 121.2(4) . . ? C16 C15 C14 121.6(5) . . ? C15 C16 C17 119.6(4) . . ? C16 C17 C12 118.7(4) . . ? C16 C17 C18 124.6(4) . . ? C12 C17 C18 116.7(4) . . ? C19 C18 C17 120.2(4) . . ? C18 C19 C20 119.4(4) . . ? N11 C20 C19 122.3(4) . . ? N11 C20 C21 115.4(4) . . ? C19 C20 C21 122.3(4) . . ? N22 C21 C20 115.0(4) . . ? C21 N22 N23 120.5(4) . . ? C21 N22 Y 123.3(3) . . ? N23 N22 Y 116.1(3) . . ? N22 N23 C24 114.6(4) . . ? O26 C24 N25 123.8(5) . . ? O26 C24 N23 120.9(4) . . ? N25 C24 N23 115.2(4) . . ? C24 O26 Y 125.0(3) . . ? C32 O31 Y 135.5(3) . . ? O31 C32 N33 123.9(5) . . ? C32 N33 C35 122.5(5) . . ? C32 N33 C34 121.6(6) . . ? C35 N33 C34 115.8(6) . . ? C42 O41 Y 132.3(3) . . ? O41 C42 N43 123.3(5) . . ? C42 N43 C45 121.8(4) . . ? C42 N43 C44 120.7(5) . . ? C45 N43 C44 117.4(5) . . ? O53 N51 O52 120.4(4) . . ? O53 N51 O54 120.3(4) . . ? O52 N51 O54 119.3(5) . . ? O53 N51 Y 59.2(2) . . ? O52 N51 Y 61.3(2) . . ? O54 N51 Y 173.8(3) . . ? N51 O52 Y 93.0(3) . . ? N51 O53 Y 96.0(3) . . ? N73 C72 O71 113.7(14) . . ? C72 N73 C74 137.4(12) . . ? C72 N73 C75 117.3(12) . . ? C74 N73 C75 104.9(11) . . ? 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 O13 Y N11 C20 173.2(4) . . . . ? O31 Y N11 C20 71.5(4) . . . . ? O41 Y N11 C20 -117.7(4) . . . . ? O13 Y N11 C20 134.3(3) 2_765 . . . ? O26 Y N11 C20 3.1(4) . . . . ? O53 Y N11 C20 -62.9(4) . . . . ? O52 Y N11 C20 -113.1(4) . . . . ? N22 Y N11 C20 2.2(3) . . . . ? N51 Y N11 C20 -87.4(4) . . . . ? Y Y N11 C20 154.8(3) 2_765 . . . ? O13 Y N11 C12 -12.7(3) . . . . ? O31 Y N11 C12 -114.5(3) . . . . ? O41 Y N11 C12 56.3(4) . . . . ? O13 Y N11 C12 -51.7(3) 2_765 . . . ? O26 Y N11 C12 177.1(3) . . . . ? O53 Y N11 C12 111.1(3) . . . . ? O52 Y N11 C12 60.9(3) . . . . ? N22 Y N11 C12 176.2(3) . . . . ? N51 Y N11 C12 86.7(3) . . . . ? Y Y N11 C12 -31.2(3) 2_765 . . . ? C20 N11 C12 C17 1.3(6) . . . . ? Y N11 C12 C17 -173.0(3) . . . . ? C20 N11 C12 C13 -176.5(4) . . . . ? Y N11 C12 C13 9.1(5) . . . . ? N11 C12 C13 O13 5.1(6) . . . . ? C17 C12 C13 O13 -172.8(4) . . . . ? N11 C12 C13 C14 -176.3(4) . . . . ? C17 C12 C13 C14 5.8(7) . . . . ? C14 C13 O13 Y 163.4(4) . . . . ? C12 C13 O13 Y -18.1(5) . . . . ? C14 C13 O13 Y -37.1(6) . . . 2_765 ? C12 C13 O13 Y 141.4(3) . . . 2_765 ? O31 Y O13 C13 92.9(3) . . . . ? O41 Y O13 C13 -130.6(3) . . . . ? O13 Y O13 C13 162.2(4) 2_765 . . . ? O26 Y O13 C13 160.9(5) . . . . ? N11 Y O13 C13 16.1(3) . . . . ? O53 Y O13 C13 -54.0(3) . . . . ? O52 Y O13 C13 -65.0(3) . . . . ? N22 Y O13 C13 26.0(4) . . . . ? N51 Y O13 C13 -60.7(3) . . . . ? Y Y O13 C13 162.2(4) 2_765 . . . ? O31 Y O13 Y -69.27(15) . . . 2_765 ? O41 Y O13 Y 67.26(15) . . . 2_765 ? O13 Y O13 Y 0.0 2_765 . . 2_765 ? O26 Y O13 Y -1.3(6) . . . 2_765 ? N11 Y O13 Y -146.09(17) . . . 2_765 ? O53 Y O13 Y 143.84(15) . . . 2_765 ? O52 Y O13 Y 132.79(17) . . . 2_765 ? N22 Y O13 Y -136.17(14) . . . 2_765 ? N51 Y O13 Y 137.10(13) . . . 2_765 ? O13 C13 C14 C15 174.5(5) . . . . ? C12 C13 C14 C15 -4.0(7) . . . . ? C13 C14 C15 C16 1.0(9) . . . . ? C14 C15 C16 C17 0.4(9) . . . . ? C15 C16 C17 C12 1.4(8) . . . . ? C15 C16 C17 C18 -179.0(6) . . . . ? N11 C12 C17 C16 177.6(4) . . . . ? C13 C12 C17 C16 -4.6(7) . . . . ? N11 C12 C17 C18 -2.0(7) . . . . ? C13 C12 C17 C18 175.8(5) . . . . ? C16 C17 C18 C19 -179.4(5) . . . . ? C12 C17 C18 C19 0.3(8) . . . . ? C17 C18 C19 C20 2.0(8) . . . . ? C12 N11 C20 C19 1.1(7) . . . . ? Y N11 C20 C19 174.9(4) . . . . ? C12 N11 C20 C21 -178.4(4) . . . . ? Y N11 C20 C21 -4.6(5) . . . . ? C18 C19 C20 N11 -2.8(8) . . . . ? C18 C19 C20 C21 176.7(5) . . . . ? N11 C20 C21 N22 4.9(6) . . . . ? C19 C20 C21 N22 -174.7(5) . . . . ? C20 C21 N22 N23 -179.1(4) . . . . ? C20 C21 N22 Y -3.2(6) . . . . ? O13 Y N22 C21 -9.6(4) . . . . ? O31 Y N22 C21 -90.8(4) . . . . ? O41 Y N22 C21 139.4(4) . . . . ? O13 Y N22 C21 -109.8(4) 2_765 . . . ? O26 Y N22 C21 -178.3(4) . . . . ? N11 Y N22 C21 0.8(3) . . . . ? O53 Y N22 C21 98.6(4) . . . . ? O52 Y N22 C21 64.1(4) . . . . ? N51 Y N22 C21 81.9(4) . . . . ? Y Y N22 C21 -53.3(4) 2_765 . . . ? O13 Y N22 N23 166.5(3) . . . . ? O31 Y N22 N23 85.2(3) . . . . ? O41 Y N22 N23 -44.6(4) . . . . ? O13 Y N22 N23 66.2(4) 2_765 . . . ? O26 Y N22 N23 -2.3(3) . . . . ? N11 Y N22 N23 176.8(4) . . . . ? O53 Y N22 N23 -85.4(3) . . . . ? O52 Y N22 N23 -119.8(3) . . . . ? N51 Y N22 N23 -102.0(3) . . . . ? Y Y N22 N23 122.8(3) 2_765 . . . ? C21 N22 N23 C24 177.0(4) . . . . ? Y N22 N23 C24 0.8(5) . . . . ? N22 N23 C24 O26 2.8(7) . . . . ? N22 N23 C24 N25 -177.0(5) . . . . ? N25 C24 O26 Y 174.2(4) . . . . ? N23 C24 O26 Y -5.7(7) . . . . ? O13 Y O26 C24 -136.7(5) . . . . ? O31 Y O26 C24 -66.5(4) . . . . ? O41 Y O26 C24 152.4(4) . . . . ? O13 Y O26 C24 -137.9(4) 2_765 . . . ? N11 Y O26 C24 3.3(5) . . . . ? O53 Y O26 C24 74.9(4) . . . . ? O52 Y O26 C24 94.4(4) . . . . ? N22 Y O26 C24 4.2(4) . . . . ? N51 Y O26 C24 85.1(4) . . . . ? Y Y O26 C24 -137.7(4) 2_765 . . . ? O13 Y O31 C32 50.5(5) . . . . ? O41 Y O31 C32 -57.1(6) . . . . ? O13 Y O31 C32 -14.6(5) 2_765 . . . ? O26 Y O31 C32 -116.1(5) . . . . ? N11 Y O31 C32 115.5(5) . . . . ? O53 Y O31 C32 -170.1(5) . . . . ? O52 Y O31 C32 105.1(5) . . . . ? N22 Y O31 C32 178.2(5) . . . . ? N51 Y O31 C32 163.1(4) . . . . ? Y Y O31 C32 18.5(5) 2_765 . . . ? Y O31 C32 N33 126.3(5) . . . . ? O31 C32 N33 C35 -1.7(9) . . . . ? O31 C32 N33 C34 -178.7(6) . . . . ? O13 Y O41 C42 -148.9(4) . . . . ? O31 Y O41 C42 -41.5(5) . . . . ? O13 Y O41 C42 -84.4(4) 2_765 . . . ? O26 Y O41 C42 17.6(4) . . . . ? N11 Y O41 C42 151.2(4) . . . . ? O53 Y O41 C42 93.7(4) . . . . ? O52 Y O41 C42 146.5(4) . . . . ? N22 Y O41 C42 55.5(5) . . . . ? N51 Y O41 C42 119.2(4) . . . . ? Y Y O41 C42 -117.3(4) 2_765 . . . ? Y O41 C42 N43 150.8(4) . . . . ? O41 C42 N43 C45 -2.1(8) . . . . ? O41 C42 N43 C44 -179.5(5) . . . . ? O13 Y N51 O53 165.8(3) . . . . ? O31 Y N51 O53 52.5(4) . . . . ? O41 Y N51 O53 -98.0(3) . . . . ? O13 Y N51 O53 -130.6(3) 2_765 . . . ? O26 Y N51 O53 -23.7(3) . . . . ? N11 Y N51 O53 100.4(3) . . . . ? O52 Y N51 O53 175.1(4) . . . . ? N22 Y N51 O53 38.5(3) . . . . ? Y Y N51 O53 -168.4(3) 2_765 . . . ? O13 Y N51 O52 -9.3(3) . . . . ? O31 Y N51 O52 -122.6(3) . . . . ? O41 Y N51 O52 86.9(3) . . . . ? O13 Y N51 O52 54.3(3) 2_765 . . . ? O26 Y N51 O52 161.2(3) . . . . ? N11 Y N51 O52 -74.8(3) . . . . ? O53 Y N51 O52 -175.1(4) . . . . ? N22 Y N51 O52 -136.6(3) . . . . ? Y Y N51 O52 16.5(3) 2_765 . . . ? O13 Y N51 O54 -107(3) . . . . ? O31 Y N51 O54 139(3) . . . . ? O41 Y N51 O54 -11(3) . . . . ? O13 Y N51 O54 -44(3) 2_765 . . . ? O26 Y N51 O54 63(3) . . . . ? N11 Y N51 O54 -173(3) . . . . ? O53 Y N51 O54 87(3) . . . . ? O52 Y N51 O54 -98(3) . . . . ? N22 Y N51 O54 126(3) . . . . ? Y Y N51 O54 -81(3) 2_765 . . . ? O53 N51 O52 Y -4.9(4) . . . . ? O54 N51 O52 Y 172.9(3) . . . . ? O13 Y O52 N51 170.0(3) . . . . ? O31 Y O52 N51 110.0(3) . . . . ? O41 Y O52 N51 -83.5(3) . . . . ? O13 Y O52 N51 -139.8(2) 2_765 . . . ? O26 Y O52 N51 -21.8(3) . . . . ? N11 Y O52 N51 99.3(3) . . . . ? O53 Y O52 N51 2.7(2) . . . . ? N22 Y O52 N51 44.7(3) . . . . ? Y Y O52 N51 -165.5(2) 2_765 . . . ? O52 N51 O53 Y 5.0(4) . . . . ? O54 N51 O53 Y -172.8(3) . . . . ? O13 Y O53 N51 -16.2(3) . . . . ? O31 Y O53 N51 -149.0(3) . . . . ? O41 Y O53 N51 74.0(3) . . . . ? O13 Y O53 N51 77.3(4) 2_765 . . . ? O26 Y O53 N51 155.4(3) . . . . ? N11 Y O53 N51 -76.3(3) . . . . ? O52 Y O53 N51 -2.7(2) . . . . ? N22 Y O53 N51 -137.2(3) . . . . ? Y Y O53 N51 16.9(4) 2_765 . . . ? O71 C72 N73 C74 172.1(13) . . . . ? O71 C72 N73 C75 0.2(19) . . . . ? _diffrn_measured_fraction_theta_max 0.993 _diffrn_reflns_theta_full 27.91 _diffrn_measured_fraction_theta_full 0.993 _refine_diff_density_max 3.026 _refine_diff_density_min -1.400 _refine_diff_density_rms 0.131