# Electronic Supplementary Material (ESI) for Dalton Transactions # This journal is © The Royal Society of Chemistry 2012 data_global _journal_name_full 'Dalton Trans.' _journal_coden_cambridge 0222 _journal_year ? _journal_volume ? _journal_page_first ? _publ_contact_author_name 'Zhang, Hongjie' _publ_contact_author_email hongjie@ciac.jl.cn _publ_author_name 'Hongjie Zhang' data_l _database_code_depnum_ccdc_archive 'CCDC 857002' #TrackingRef '- 1-12 and 7.CIF' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point 'not measured' _chemical_formula_moiety 'C21 H20.50 La N3 O11.25' _chemical_formula_sum 'C21 H20.50 La N3 O11.25' _chemical_formula_weight 633.81 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 C2/c loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y, -z+1/2' 'x+1/2, y+1/2, z' '-x+1/2, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y, z-1/2' '-x+1/2, -y+1/2, -z' 'x+1/2, -y+1/2, z-1/2' _cell_length_a 23.7369(11) _cell_length_b 15.8216(7) _cell_length_c 16.2890(8) _cell_angle_alpha 90.00 _cell_angle_beta 124.0540(10) _cell_angle_gamma 90.00 _cell_volume 5068.3(4) _cell_formula_units_Z 8 _cell_measurement_temperature 185(2) _cell_measurement_reflns_used 5023 _cell_measurement_theta_min 1.80 _cell_measurement_theta_max 26.10 _exptl_crystal_description rod _exptl_crystal_colour 'light yellow' _exptl_crystal_size_max 0.26 _exptl_crystal_size_mid 0.21 _exptl_crystal_size_min 0.18 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.661 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 2516 _exptl_absorpt_coefficient_mu 1.749 _exptl_absorpt_correction_type empirical _exptl_absorpt_correction_T_min 0.6592 _exptl_absorpt_correction_T_max 0.7437 _exptl_absorpt_process_details SADABS _exptl_special_details ; ? ; _diffrn_ambient_temperature 185(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'CCD area detector' _diffrn_measurement_method 'phi and omega scans' _diffrn_detector_area_resol_mean 9.00cm _diffrn_standards_number none _diffrn_standards_interval_count none _diffrn_standards_interval_time none _diffrn_standards_decay_% none _diffrn_reflns_number 13836 _diffrn_reflns_av_R_equivalents 0.0386 _diffrn_reflns_av_sigmaI/netI 0.0469 _diffrn_reflns_limit_h_min -29 _diffrn_reflns_limit_h_max 29 _diffrn_reflns_limit_k_min -14 _diffrn_reflns_limit_k_max 19 _diffrn_reflns_limit_l_min -20 _diffrn_reflns_limit_l_max 17 _diffrn_reflns_theta_min 1.80 _diffrn_reflns_theta_max 26.10 _reflns_number_total 5023 _reflns_number_gt 4174 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SMART' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics SHELXP-97 _computing_publication_material SHELXTL _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0393P)^2^+26.6307P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 5023 _refine_ls_number_parameters 295 _refine_ls_number_restraints 6 _refine_ls_R_factor_all 0.0492 _refine_ls_R_factor_gt 0.0396 _refine_ls_wR_factor_ref 0.0969 _refine_ls_wR_factor_gt 0.0916 _refine_ls_goodness_of_fit_ref 1.056 _refine_ls_restrained_S_all 1.056 _refine_ls_shift/su_max 0.001 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group La1 La 0.188743(12) 0.330442(16) 0.378405(17) 0.01607(9) Uani 1 1 d . . . C1 C 0.0202(2) 0.2611(3) 0.0791(3) 0.0206(10) Uani 1 1 d . . . C2 C -0.0453(2) 0.2576(3) 0.0574(3) 0.0211(10) Uani 1 1 d . . . H2A H -0.0547 0.2802 0.1025 0.025 Uiso 1 1 calc R . . C3 C -0.0967(2) 0.2210(3) -0.0306(3) 0.0206(10) Uani 1 1 d . . . C4 C -0.0827(2) 0.1853(3) -0.0950(3) 0.0242(10) Uani 1 1 d . . . H4A H -0.1177 0.1589 -0.1545 0.029 Uiso 1 1 calc R . . C5 C -0.0172(2) 0.1887(3) -0.0714(3) 0.0244(10) Uani 1 1 d . . . C6 C 0.0347(2) 0.2268(3) 0.0140(3) 0.0226(10) Uani 1 1 d . . . H6A H 0.0794 0.2297 0.0283 0.027 Uiso 1 1 calc R . . C7 C -0.0434(2) 0.0932(3) -0.1987(3) 0.0269(11) Uani 1 1 d . . . C8 C -0.0969(2) 0.1099(3) -0.2958(3) 0.0248(10) Uani 1 1 d . . . C9 C -0.1387(2) 0.0449(3) -0.3569(3) 0.0237(10) Uani 1 1 d . . . H9A H -0.1751 0.0566 -0.4233 0.028 Uiso 1 1 calc R . . C10 C -0.1273(2) -0.0370(3) -0.3212(3) 0.0231(10) Uani 1 1 d . . . C11 C -0.0725(2) -0.0537(3) -0.2252(3) 0.0295(11) Uani 1 1 d . . . H11A H -0.0638 -0.1100 -0.2008 0.035 Uiso 1 1 calc R . . C12 C -0.0306(3) 0.0108(3) -0.1651(4) 0.0317(12) Uani 1 1 d . . . H12A H 0.0074 -0.0015 -0.1002 0.038 Uiso 1 1 calc R . . C13 C 0.0777(2) 0.2997(3) 0.1752(3) 0.0217(10) Uani 1 1 d . . . C14 C -0.1691(2) 0.2180(3) -0.0609(3) 0.0219(10) Uani 1 1 d . . . C15 C -0.1753(2) -0.1067(3) -0.3847(3) 0.0243(10) Uani 1 1 d . . . C19 C 0.0699(3) 0.4589(4) 0.3886(5) 0.0510(6) Uani 1 1 d . A . H19A H 0.0320 0.4250 0.3427 0.061 Uiso 1 1 calc R . . C20 C -0.0117(3) 0.5607(4) 0.3691(5) 0.0510(6) Uani 1 1 d . . . H20A H -0.0433 0.5157 0.3273 0.076 Uiso 1 1 calc R . . H20B H -0.0206 0.6112 0.3288 0.076 Uiso 1 1 calc R . . H20C H -0.0182 0.5740 0.4221 0.076 Uiso 1 1 calc R . . C21 C 0.1131(3) 0.5898(4) 0.4783(5) 0.0510(6) Uani 1 1 d . . . H21A H 0.1567 0.5628 0.5012 0.076 Uiso 1 1 calc R . . H21B H 0.1112 0.6032 0.5354 0.076 Uiso 1 1 calc R . . H21C H 0.1087 0.6420 0.4427 0.076 Uiso 1 1 calc R . . N1 N -0.1132(2) 0.1954(3) -0.3375(4) 0.0359(11) Uani 1 1 d . . . N2 N 0.2283(3) 0.5907(3) 0.2855(4) 0.0572(8) Uani 1 1 d . . . N3 N 0.0578(3) 0.5327(3) 0.4123(4) 0.0510(6) Uani 1 1 d . . . O1 O 0.13566(15) 0.3028(2) 0.1915(2) 0.0245(7) Uani 1 1 d . . . O2 O 0.06467(15) 0.3259(2) 0.2361(2) 0.0268(8) Uani 1 1 d . . . O3 O -0.18684(15) 0.2579(2) -0.0113(2) 0.0246(7) Uani 1 1 d . . . O4 O -0.21107(16) 0.1758(2) -0.1361(2) 0.0313(8) Uani 1 1 d . . . O5 O -0.0894(3) 0.2560(3) -0.2822(3) 0.0677(15) Uani 1 1 d . . . O6 O -0.1498(2) 0.2026(3) -0.4282(3) 0.0560(12) Uani 1 1 d . . . O7 O -0.22010(16) -0.0887(2) -0.4734(2) 0.0302(8) Uani 1 1 d . . . O8 O -0.16702(19) -0.1764(2) -0.3437(2) 0.0334(8) Uani 1 1 d . . . O9 O 0.00012(17) 0.1554(2) -0.1342(3) 0.0341(9) Uani 1 1 d . . . O10 O 0.1865(2) 0.4705(3) 0.3043(3) 0.0572(8) Uani 1 1 d . . . O11 O 0.1274(2) 0.4307(3) 0.4221(3) 0.0510(6) Uani 1 1 d . . . O1W O -0.2509(15) 0.145(2) -0.336(2) 0.117(9) Uani 0.25 1 d PU . . C16 C 0.2090(6) 0.5431(8) 0.3290(10) 0.0572(8) Uani 0.60 1 d P A 1 H16 H 0.2122 0.5658 0.3855 0.080 Uiso 0.60 1 calc PR A 1 C16' C 0.2327(10) 0.5193(11) 0.3347(15) 0.0572(8) Uani 0.40 1 d P A 2 H16' H 0.2742 0.5075 0.3961 0.080 Uiso 0.40 1 calc PR A 2 C17 C 0.2493(6) 0.6814(7) 0.3209(8) 0.0572(8) Uani 0.60 1 d P A 1 H17A H 0.2587 0.6873 0.3874 0.086 Uiso 0.60 1 calc PR A 1 H17B H 0.2124 0.7198 0.2752 0.086 Uiso 0.60 1 calc PR A 1 H17C H 0.2903 0.6953 0.3229 0.086 Uiso 0.60 1 calc PR A 1 C17' C 0.2892(9) 0.6421(11) 0.3235(12) 0.0572(8) Uani 0.40 1 d P A 2 H17D H 0.3052 0.6627 0.3899 0.086 Uiso 0.40 1 calc PR A 2 H17E H 0.2785 0.6902 0.2792 0.086 Uiso 0.40 1 calc PR A 2 H17F H 0.3248 0.6077 0.3269 0.086 Uiso 0.40 1 calc PR A 2 C18 C 0.1803(6) 0.5873(7) 0.1731(8) 0.0572(8) Uani 0.60 1 d P A 1 H18A H 0.1386 0.6187 0.1520 0.086 Uiso 0.60 1 calc PR A 1 H18B H 0.1688 0.5283 0.1517 0.086 Uiso 0.60 1 calc PR A 1 H18C H 0.2024 0.6128 0.1433 0.086 Uiso 0.60 1 calc PR A 1 C18' C 0.2243(10) 0.5717(11) 0.2000(13) 0.0572(8) Uani 0.40 1 d P A 2 H18D H 0.2131 0.5118 0.1842 0.086 Uiso 0.40 1 calc PR A 2 H18E H 0.2681 0.5835 0.2095 0.086 Uiso 0.40 1 calc PR A 2 H18F H 0.1888 0.6063 0.1455 0.086 Uiso 0.40 1 calc PR A 2 loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 La1 0.01309(14) 0.01669(15) 0.01356(13) -0.00032(10) 0.00447(10) -0.00135(10) C1 0.020(2) 0.021(2) 0.017(2) 0.0003(18) 0.0078(19) 0.0010(18) C2 0.019(2) 0.025(2) 0.018(2) -0.0023(18) 0.0094(19) 0.0020(19) C3 0.021(2) 0.022(2) 0.020(2) -0.0029(18) 0.0120(19) -0.0005(19) C4 0.019(2) 0.032(3) 0.018(2) -0.0087(19) 0.0088(19) -0.006(2) C5 0.023(2) 0.027(3) 0.026(2) -0.010(2) 0.015(2) -0.006(2) C6 0.018(2) 0.022(2) 0.023(2) -0.0041(19) 0.0091(19) -0.0038(19) C7 0.023(2) 0.035(3) 0.026(2) -0.017(2) 0.017(2) -0.013(2) C8 0.029(3) 0.021(2) 0.031(3) -0.004(2) 0.021(2) -0.004(2) C9 0.024(2) 0.024(3) 0.020(2) -0.0043(19) 0.010(2) -0.005(2) C10 0.025(2) 0.023(2) 0.019(2) -0.0043(18) 0.010(2) -0.001(2) C11 0.032(3) 0.023(3) 0.023(2) 0.001(2) 0.008(2) 0.000(2) C12 0.026(3) 0.040(3) 0.023(2) -0.006(2) 0.009(2) -0.006(2) C13 0.019(2) 0.024(2) 0.016(2) -0.0001(18) 0.0058(19) -0.0010(19) C14 0.018(2) 0.025(3) 0.020(2) 0.0022(19) 0.0093(19) 0.0022(19) C15 0.026(2) 0.022(3) 0.022(2) -0.0058(19) 0.012(2) -0.006(2) C19 0.0481(14) 0.0414(14) 0.0579(15) -0.0059(11) 0.0262(13) 0.0129(11) C20 0.0481(14) 0.0414(14) 0.0579(15) -0.0059(11) 0.0262(13) 0.0129(11) C21 0.0481(14) 0.0414(14) 0.0579(15) -0.0059(11) 0.0262(13) 0.0129(11) N1 0.045(3) 0.024(2) 0.048(3) -0.007(2) 0.032(2) -0.008(2) N2 0.062(2) 0.0448(18) 0.0536(17) 0.0109(14) 0.0259(16) -0.0160(15) N3 0.0481(14) 0.0414(14) 0.0579(15) -0.0059(11) 0.0262(13) 0.0129(11) O1 0.0165(16) 0.037(2) 0.0189(16) -0.0030(14) 0.0089(13) -0.0039(14) O2 0.0167(16) 0.040(2) 0.0180(15) -0.0098(14) 0.0060(13) 0.0014(14) O3 0.0231(17) 0.0290(19) 0.0262(17) -0.0033(14) 0.0166(15) -0.0004(14) O4 0.0174(16) 0.050(2) 0.0251(17) -0.0155(16) 0.0108(14) -0.0073(16) O5 0.118(4) 0.026(2) 0.062(3) -0.014(2) 0.053(3) -0.022(3) O6 0.058(3) 0.037(2) 0.051(3) 0.006(2) 0.017(2) -0.002(2) O7 0.0254(18) 0.0250(18) 0.0233(17) -0.0055(14) 0.0033(15) -0.0051(15) O8 0.044(2) 0.0193(19) 0.0246(17) -0.0049(14) 0.0111(16) -0.0067(16) O9 0.0242(18) 0.048(2) 0.0366(19) -0.0282(17) 0.0212(16) -0.0205(16) O10 0.062(2) 0.0448(18) 0.0536(17) 0.0109(14) 0.0259(16) -0.0160(15) O11 0.0481(14) 0.0414(14) 0.0579(15) -0.0059(11) 0.0262(13) 0.0129(11) O1W 0.115(12) 0.127(13) 0.114(12) -0.016(9) 0.066(9) 0.016(9) C16 0.062(2) 0.0448(18) 0.0536(17) 0.0109(14) 0.0259(16) -0.0160(15) C16' 0.062(2) 0.0448(18) 0.0536(17) 0.0109(14) 0.0259(16) -0.0160(15) C17 0.062(2) 0.0448(18) 0.0536(17) 0.0109(14) 0.0259(16) -0.0160(15) C17' 0.062(2) 0.0448(18) 0.0536(17) 0.0109(14) 0.0259(16) -0.0160(15) C18 0.062(2) 0.0448(18) 0.0536(17) 0.0109(14) 0.0259(16) -0.0160(15) C18' 0.062(2) 0.0448(18) 0.0536(17) 0.0109(14) 0.0259(16) -0.0160(15) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag La1 O3 2.473(3) 2 ? La1 O8 2.490(3) 5 ? La1 O7 2.509(3) 3_556 ? La1 O10 2.509(4) . ? La1 O11 2.512(4) . ? La1 O4 2.520(3) 8_556 ? La1 O2 2.531(3) . ? La1 O1 2.599(3) . ? La1 O3 2.821(3) 8_556 ? La1 C13 2.893(4) . ? La1 C14 3.035(4) 8_556 ? C1 C2 1.389(6) . ? C1 C6 1.395(6) . ? C1 C13 1.514(6) . ? C2 C3 1.386(6) . ? C3 C4 1.387(6) . ? C3 C14 1.500(6) . ? C4 C5 1.378(6) . ? C5 C6 1.378(6) . ? C5 O9 1.401(6) . ? C7 C12 1.380(7) . ? C7 O9 1.387(5) . ? C7 C8 1.391(7) . ? C8 C9 1.388(6) . ? C8 N1 1.465(7) . ? C9 C10 1.384(7) . ? C10 C11 1.389(6) . ? C10 C15 1.504(6) . ? C11 C12 1.377(7) . ? C13 O1 1.249(5) . ? C13 O2 1.262(5) . ? C14 O4 1.253(5) . ? C14 O3 1.268(5) . ? C14 La1 3.035(4) 8_455 ? C15 O8 1.246(6) . ? C15 O7 1.257(5) . ? C19 O11 1.235(7) . ? C19 N3 1.311(7) . ? C20 N3 1.454(7) . ? C21 N3 1.454(8) . ? N1 O5 1.217(6) . ? N1 O6 1.230(6) . ? N2 C16 1.283(13) . ? N2 C16' 1.356(18) . ? N2 C18' 1.374(18) . ? N2 C17' 1.460(16) . ? N2 C18 1.521(12) . ? N2 C17 1.521(12) . ? O3 La1 2.473(3) 2 ? O3 La1 2.821(3) 8_455 ? O4 La1 2.520(3) 8_455 ? O7 La1 2.509(3) 3_444 ? O8 La1 2.490(3) 5 ? O10 C16' 1.198(18) . ? O10 C16 1.235(13) . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag O3 La1 O8 68.99(11) 2 5 ? O3 La1 O7 79.82(11) 2 3_556 ? O8 La1 O7 132.46(11) 5 3_556 ? O3 La1 O10 145.60(13) 2 . ? O8 La1 O10 144.02(13) 5 . ? O7 La1 O10 77.69(13) 3_556 . ? O3 La1 O11 75.35(13) 2 . ? O8 La1 O11 127.11(14) 5 . ? O7 La1 O11 74.33(13) 3_556 . ? O10 La1 O11 73.71(15) . . ? O3 La1 O4 122.99(10) 2 8_556 ? O8 La1 O4 91.52(13) 5 8_556 ? O7 La1 O4 76.08(12) 3_556 8_556 ? O10 La1 O4 75.90(14) . 8_556 ? O11 La1 O4 141.19(13) . 8_556 ? O3 La1 O2 101.89(11) 2 . ? O8 La1 O2 77.12(11) 5 . ? O7 La1 O2 146.10(11) 3_556 . ? O10 La1 O2 83.38(13) . . ? O11 La1 O2 73.47(12) . . ? O4 La1 O2 126.03(10) 8_556 . ? O3 La1 O1 135.47(10) 2 . ? O8 La1 O1 70.49(11) 5 . ? O7 La1 O1 143.53(11) 3_556 . ? O10 La1 O1 73.71(13) . . ? O11 La1 O1 117.45(12) . . ? O4 La1 O1 75.37(10) 8_556 . ? O2 La1 O1 50.96(10) . . ? O3 La1 O3 74.83(11) 2 8_556 ? O8 La1 O3 70.70(11) 5 8_556 ? O7 La1 O3 66.97(10) 3_556 8_556 ? O10 La1 O3 118.43(13) . 8_556 ? O11 La1 O3 134.34(12) . 8_556 ? O4 La1 O3 48.23(9) 8_556 8_556 ? O2 La1 O3 146.64(10) . 8_556 ? O1 La1 O3 108.08(10) . 8_556 ? O3 La1 C13 118.14(12) 2 . ? O8 La1 C13 68.62(12) 5 . ? O7 La1 C13 158.25(12) 3_556 . ? O10 La1 C13 80.69(14) . . ? O11 La1 C13 97.39(13) . . ? O4 La1 C13 100.94(12) 8_556 . ? O2 La1 C13 25.81(12) . . ? O1 La1 C13 25.58(11) . . ? O3 La1 C13 127.13(12) 8_556 . ? O3 La1 C14 99.17(11) 2 8_556 ? O8 La1 C14 82.99(13) 5 8_556 ? O7 La1 C14 67.22(12) 3_556 8_556 ? O10 La1 C14 95.72(14) . 8_556 ? O11 La1 C14 141.50(13) . 8_556 ? O4 La1 C14 23.85(11) 8_556 8_556 ? O2 La1 C14 143.35(11) . 8_556 ? O1 La1 C14 93.46(11) . 8_556 ? O3 La1 C14 24.66(10) 8_556 8_556 ? C13 La1 C14 117.72(13) . 8_556 ? C2 C1 C6 120.6(4) . . ? C2 C1 C13 120.7(4) . . ? C6 C1 C13 118.7(4) . . ? C3 C2 C1 119.5(4) . . ? C2 C3 C4 120.5(4) . . ? C2 C3 C14 122.5(4) . . ? C4 C3 C14 117.0(4) . . ? C5 C4 C3 119.0(4) . . ? C4 C5 C6 122.0(4) . . ? C4 C5 O9 121.9(4) . . ? C6 C5 O9 116.1(4) . . ? C5 C6 C1 118.5(4) . . ? C12 C7 O9 117.7(4) . . ? C12 C7 C8 119.2(4) . . ? O9 C7 C8 123.0(5) . . ? C9 C8 C7 120.4(4) . . ? C9 C8 N1 117.0(4) . . ? C7 C8 N1 122.6(4) . . ? C10 C9 C8 119.9(4) . . ? C9 C10 C11 119.4(4) . . ? C9 C10 C15 120.2(4) . . ? C11 C10 C15 120.4(4) . . ? C12 C11 C10 120.5(5) . . ? C11 C12 C7 120.5(5) . . ? O1 C13 O2 123.1(4) . . ? O1 C13 C1 118.8(4) . . ? O2 C13 C1 118.1(4) . . ? O1 C13 La1 63.9(2) . . ? O2 C13 La1 60.9(2) . . ? C1 C13 La1 165.2(3) . . ? O4 C14 O3 121.5(4) . . ? O4 C14 C3 118.4(4) . . ? O3 C14 C3 120.2(4) . . ? O4 C14 La1 54.4(2) . 8_455 ? O3 C14 La1 68.2(2) . 8_455 ? C3 C14 La1 167.2(3) . 8_455 ? O8 C15 O7 126.5(4) . . ? O8 C15 C10 116.6(4) . . ? O7 C15 C10 116.9(4) . . ? O11 C19 N3 124.2(6) . . ? O5 N1 O6 122.7(5) . . ? O5 N1 C8 119.4(5) . . ? O6 N1 C8 117.9(4) . . ? C16 N2 C16' 27.8(9) . . ? C16 N2 C18' 126.0(10) . . ? C16' N2 C18' 110.9(12) . . ? C16 N2 C17' 131.9(10) . . ? C16' N2 C17' 118.9(11) . . ? C18' N2 C17' 92.4(11) . . ? C16 N2 C18 112.6(8) . . ? C16' N2 C18 116.1(10) . . ? C18' N2 C18 36.3(8) . . ? C17' N2 C18 115.3(8) . . ? C16 N2 C17 119.1(9) . . ? C16' N2 C17 131.3(10) . . ? C18' N2 C17 114.4(9) . . ? C17' N2 C17 43.8(8) . . ? C18 N2 C17 110.8(7) . . ? C19 N3 C21 121.0(5) . . ? C19 N3 C20 120.3(6) . . ? C21 N3 C20 118.6(5) . . ? C13 O1 La1 90.5(3) . . ? C13 O2 La1 93.3(3) . . ? C14 O3 La1 164.5(3) . 2 ? C14 O3 La1 87.1(3) . 8_455 ? La1 O3 La1 105.17(10) 2 8_455 ? C14 O4 La1 101.8(3) . 8_455 ? C15 O7 La1 135.2(3) . 3_444 ? C15 O8 La1 142.6(3) . 5 ? C7 O9 C5 114.8(3) . . ? C16' O10 C16 30.4(10) . . ? C16' O10 La1 127.1(9) . . ? C16 O10 La1 140.9(7) . . ? C19 O11 La1 140.9(4) . . ? O10 C16 N2 126.1(12) . . ? O10 C16' N2 122.9(16) . . ? _diffrn_measured_fraction_theta_max 0.997 _diffrn_reflns_theta_full 26.10 _diffrn_measured_fraction_theta_full 0.997 _refine_diff_density_max 1.684 _refine_diff_density_min -2.098 _refine_diff_density_rms 0.123 data_2 _database_code_depnum_ccdc_archive 'CCDC 857003' #TrackingRef '- 1-12 and 7.CIF' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point 'not measured' _chemical_formula_moiety 'C21 H20.50 Ce N3 O11.25' _chemical_formula_sum 'C21 H20.50 Ce N3 O11.25' _chemical_formula_weight 635.02 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Ce Ce -0.2486 2.6331 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Monoclinic _symmetry_space_group_name_H-M C2/c loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y, -z+1/2' 'x+1/2, y+1/2, z' '-x+1/2, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y, z-1/2' '-x+1/2, -y+1/2, -z' 'x+1/2, -y+1/2, z-1/2' _cell_length_a 23.659(7) _cell_length_b 15.770(4) _cell_length_c 16.214(9) _cell_angle_alpha 90.00 _cell_angle_beta 123.982(3) _cell_angle_gamma 90.00 _cell_volume 5017(3) _cell_formula_units_Z 8 _cell_measurement_temperature 185(2) _cell_measurement_reflns_used 4999 _cell_measurement_theta_min 1.66 _cell_measurement_theta_max 26.16 _exptl_crystal_description rod _exptl_crystal_colour 'light yellow' _exptl_crystal_size_max 0.23 _exptl_crystal_size_mid 0.20 _exptl_crystal_size_min 0.14 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.682 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 2524 _exptl_absorpt_coefficient_mu 1.878 _exptl_absorpt_correction_type empirical _exptl_absorpt_correction_T_min 0.6719 _exptl_absorpt_correction_T_max 0.7789 _exptl_absorpt_process_details SADABS _exptl_special_details ; ? ; _diffrn_ambient_temperature 185(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'CCD area detector' _diffrn_measurement_method 'phi and omega scans' _diffrn_detector_area_resol_mean 9.00cm _diffrn_standards_number none _diffrn_standards_interval_count none _diffrn_standards_interval_time none _diffrn_standards_decay_% none _diffrn_reflns_number 13671 _diffrn_reflns_av_R_equivalents 0.0387 _diffrn_reflns_av_sigmaI/netI 0.0471 _diffrn_reflns_limit_h_min -16 _diffrn_reflns_limit_h_max 29 _diffrn_reflns_limit_k_min -19 _diffrn_reflns_limit_k_max 19 _diffrn_reflns_limit_l_min -20 _diffrn_reflns_limit_l_max 17 _diffrn_reflns_theta_min 1.66 _diffrn_reflns_theta_max 26.16 _reflns_number_total 4999 _reflns_number_gt 4236 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SMART' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics SHELXP-97 _computing_publication_material SHELXTL _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0603P)^2^+37.5715P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 4999 _refine_ls_number_parameters 286 _refine_ls_number_restraints 6 _refine_ls_R_factor_all 0.0530 _refine_ls_R_factor_gt 0.0450 _refine_ls_wR_factor_ref 0.1226 _refine_ls_wR_factor_gt 0.1171 _refine_ls_goodness_of_fit_ref 1.071 _refine_ls_restrained_S_all 1.070 _refine_ls_shift/su_max 0.001 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group Ce1 Ce 0.189165(13) 0.830063(17) 0.378502(19) 0.01449(11) Uani 1 1 d . . . C1 C 0.4025(3) 0.7790(3) 0.4698(4) 0.0185(10) Uani 1 1 d . . . C2 C 0.4548(3) 0.7424(3) 0.5588(4) 0.0197(11) Uani 1 1 d . . . H2A H 0.4455 0.7196 0.6043 0.024 Uiso 1 1 calc R . . C3 C 0.5212(3) 0.7393(3) 0.5806(4) 0.0186(10) Uani 1 1 d . . . C4 C 0.5346(3) 0.7731(3) 0.5140(4) 0.0179(10) Uani 1 1 d . . . H4A H 0.5792 0.7701 0.5277 0.022 Uiso 1 1 calc R . . C5 C 0.4825(3) 0.8109(3) 0.4280(4) 0.0227(11) Uani 1 1 d . . . C6 C 0.4169(3) 0.8142(4) 0.4050(4) 0.0226(11) Uani 1 1 d . . . H6A H 0.3818 0.8405 0.3451 0.027 Uiso 1 1 calc R . . C7 C 0.4562(3) 0.9060(4) 0.3005(4) 0.0242(12) Uani 1 1 d . . . C8 C 0.4026(3) 0.8893(3) 0.2036(4) 0.0222(11) Uani 1 1 d . . . C9 C 0.3613(3) 0.9545(3) 0.1427(4) 0.0223(11) Uani 1 1 d . . . H9A H 0.3250 0.9427 0.0760 0.027 Uiso 1 1 calc R . . C10 C 0.3723(3) 1.0365(3) 0.1780(4) 0.0212(11) Uani 1 1 d . . . C11 C 0.4268(3) 1.0531(4) 0.2742(4) 0.0292(13) Uani 1 1 d . . . H11A H 0.4352 1.1096 0.2988 0.035 Uiso 1 1 calc R . . C12 C 0.4686(3) 0.9889(4) 0.3343(4) 0.0288(13) Uani 1 1 d . . . H12A H 0.5065 1.0014 0.3997 0.035 Uiso 1 1 calc R . . C13 C 0.3305(3) 0.7810(3) 0.4395(4) 0.0194(11) Uani 1 1 d . . . C14 C 0.5779(3) 0.7012(3) 0.6765(4) 0.0190(10) Uani 1 1 d . . . C15 C 0.3239(3) 1.1068(3) 0.1137(4) 0.0224(11) Uani 1 1 d . . . C16 C 0.2178(5) 1.0332(6) 0.3304(7) 0.0698(11) Uani 1 1 d . . . H16 H 0.2394 1.0442 0.3994 0.084 Uiso 1 1 calc R . . C17 C 0.2583(5) 1.1723(5) 0.3216(7) 0.0698(11) Uani 1 1 d . . . H17A H 0.2822 1.1735 0.3941 0.105 Uiso 1 1 calc R . . H17B H 0.2226 1.2158 0.2921 0.105 Uiso 1 1 calc R . . H17C H 0.2908 1.1835 0.3035 0.105 Uiso 1 1 calc R . . C18 C 0.1894(5) 1.0844(6) 0.1781(6) 0.0698(11) Uani 1 1 d . . . H18A H 0.1690 1.0279 0.1567 0.105 Uiso 1 1 calc R . . H18B H 0.2199 1.0943 0.1560 0.105 Uiso 1 1 calc R . . H18C H 0.1534 1.1274 0.1489 0.105 Uiso 1 1 calc R . . C19 C 0.0715(4) 0.9580(4) 0.3893(6) 0.0460(7) Uani 1 1 d . . . H19A H 0.0338 0.9237 0.3433 0.055 Uiso 1 1 calc R . . C20 C 0.1130(4) 1.0890(4) 0.4790(6) 0.0460(7) Uani 1 1 d . . . H20A H 0.1570 1.0623 0.5028 0.069 Uiso 1 1 calc R . . H20B H 0.1104 1.1024 0.5358 0.069 Uiso 1 1 calc R . . H20C H 0.1086 1.1413 0.4432 0.069 Uiso 1 1 calc R . . C21 C -0.0110(4) 1.0600(5) 0.3714(6) 0.0460(7) Uani 1 1 d . . . H21A H -0.0429 1.0154 0.3288 0.069 Uiso 1 1 calc R . . H21B H -0.0201 1.1115 0.3319 0.069 Uiso 1 1 calc R . . H21C H -0.0169 1.0722 0.4254 0.069 Uiso 1 1 calc R . . N1 N 0.3865(3) 0.8036(3) 0.1615(4) 0.0335(12) Uani 1 1 d . . . N2 N 0.2277(4) 1.0897(5) 0.2847(5) 0.0698(11) Uani 1 1 d . . . N3 N 0.0588(3) 1.0318(4) 0.4133(5) 0.0460(7) Uani 1 1 d . . . O1 O 0.2882(2) 0.8227(3) 0.3634(3) 0.0296(9) Uani 1 1 d . . . O2 O 0.31293(19) 0.7415(2) 0.4894(3) 0.0226(8) Uani 1 1 d . . . O3 O 0.5657(2) 0.6747(2) 0.7386(3) 0.0260(9) Uani 1 1 d . . . O4 O 0.63615(18) 0.6977(3) 0.6929(3) 0.0226(8) Uani 1 1 d . . . O5 O 0.4105(3) 0.7431(3) 0.2173(4) 0.0611(16) Uani 1 1 d . . . O6 O 0.3495(3) 0.7968(3) 0.0711(4) 0.0502(13) Uani 1 1 d . . . O7 O 0.2798(2) 1.0895(2) 0.0252(3) 0.0268(9) Uani 1 1 d . . . O8 O 0.3323(2) 1.1767(2) 0.1557(3) 0.0307(10) Uani 1 1 d . . . O9 O 0.5000(2) 0.8438(3) 0.3656(3) 0.0309(10) Uani 1 1 d . . . O10 O 0.1866(3) 0.9689(4) 0.3032(4) 0.0698(11) Uani 1 1 d . . . O11 O 0.1289(3) 0.9307(3) 0.4224(4) 0.0460(7) Uani 1 1 d . . . O1W O 0.249(3) 1.347(3) 0.340(4) 0.155(17) Uani 0.25 1 d PU . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 Ce1 0.01170(17) 0.01603(17) 0.01252(17) -0.00037(10) 0.00478(13) -0.00112(10) C1 0.016(3) 0.022(3) 0.018(2) 0.001(2) 0.010(2) 0.000(2) C2 0.019(3) 0.023(3) 0.018(2) 0.004(2) 0.010(2) -0.002(2) C3 0.022(3) 0.017(2) 0.018(2) 0.002(2) 0.012(2) 0.002(2) C4 0.016(3) 0.020(3) 0.019(3) 0.002(2) 0.011(2) 0.000(2) C5 0.022(3) 0.024(3) 0.025(3) 0.010(2) 0.016(3) 0.006(2) C6 0.018(3) 0.032(3) 0.017(3) 0.008(2) 0.009(2) 0.005(2) C7 0.022(3) 0.029(3) 0.027(3) 0.014(2) 0.017(3) 0.013(2) C8 0.021(3) 0.022(3) 0.028(3) 0.005(2) 0.017(2) 0.005(2) C9 0.022(3) 0.023(3) 0.018(3) 0.004(2) 0.009(2) 0.001(2) C10 0.022(3) 0.022(3) 0.019(3) 0.003(2) 0.011(2) 0.004(2) C11 0.034(3) 0.024(3) 0.026(3) 0.004(2) 0.015(3) 0.003(2) C12 0.027(3) 0.035(3) 0.019(3) 0.008(2) 0.010(3) 0.006(3) C13 0.016(3) 0.026(3) 0.016(2) 0.001(2) 0.009(2) 0.001(2) C14 0.018(3) 0.021(3) 0.017(2) -0.002(2) 0.009(2) -0.002(2) C15 0.022(3) 0.024(3) 0.021(3) 0.007(2) 0.012(2) 0.005(2) C16 0.083(3) 0.058(2) 0.0506(19) 0.0072(16) 0.0266(19) -0.0326(18) C17 0.083(3) 0.058(2) 0.0506(19) 0.0072(16) 0.0266(19) -0.0326(18) C18 0.083(3) 0.058(2) 0.0506(19) 0.0072(16) 0.0266(19) -0.0326(18) C19 0.0462(17) 0.0368(15) 0.0549(17) -0.0064(13) 0.0282(16) 0.0100(12) C20 0.0462(17) 0.0368(15) 0.0549(17) -0.0064(13) 0.0282(16) 0.0100(12) C21 0.0462(17) 0.0368(15) 0.0549(17) -0.0064(13) 0.0282(16) 0.0100(12) N1 0.042(3) 0.023(3) 0.041(3) 0.008(2) 0.027(3) 0.008(2) N2 0.083(3) 0.058(2) 0.0506(19) 0.0072(16) 0.0266(19) -0.0326(18) N3 0.0462(17) 0.0368(15) 0.0549(17) -0.0064(13) 0.0282(16) 0.0100(12) O1 0.016(2) 0.048(3) 0.022(2) 0.0109(18) 0.0099(18) 0.0068(17) O2 0.022(2) 0.026(2) 0.024(2) 0.0033(16) 0.0159(18) 0.0001(16) O3 0.020(2) 0.038(2) 0.0192(19) 0.0096(16) 0.0102(17) 0.0000(16) O4 0.0154(19) 0.035(2) 0.0164(18) 0.0043(16) 0.0084(16) 0.0054(16) O5 0.104(5) 0.027(3) 0.054(3) 0.015(2) 0.045(4) 0.020(3) O6 0.052(3) 0.030(2) 0.045(3) -0.004(2) 0.012(3) 0.003(2) O7 0.027(2) 0.0214(19) 0.0211(19) 0.0037(16) 0.0069(18) 0.0035(16) O8 0.042(3) 0.020(2) 0.021(2) 0.0029(16) 0.012(2) 0.0087(17) O9 0.026(2) 0.041(2) 0.036(2) 0.0251(19) 0.024(2) 0.0174(18) O10 0.083(3) 0.058(2) 0.0506(19) 0.0072(16) 0.0266(19) -0.0326(18) O11 0.0462(17) 0.0368(15) 0.0549(17) -0.0064(13) 0.0282(16) 0.0100(12) O1W 0.152(19) 0.161(19) 0.157(19) -0.010(10) 0.090(13) 0.010(10) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag Ce1 O2 2.446(4) 7_566 ? Ce1 O8 2.470(4) 4_545 ? Ce1 O7 2.483(4) 6_576 ? Ce1 O11 2.487(4) . ? Ce1 O1 2.490(4) . ? Ce1 O10 2.491(5) . ? Ce1 O3 2.506(4) 8_465 ? Ce1 O4 2.570(4) 8_465 ? Ce1 O2 2.806(4) . ? Ce1 C14 2.875(5) 8_465 ? Ce1 C13 3.010(5) . ? C1 C6 1.390(7) . ? C1 C2 1.396(7) . ? C1 C13 1.486(7) . ? C2 C3 1.405(7) . ? C3 C4 1.390(7) . ? C3 C14 1.499(7) . ? C4 C5 1.378(7) . ? C5 C6 1.378(8) . ? C5 O9 1.390(6) . ? C7 C12 1.385(8) . ? C7 C8 1.386(8) . ? C7 O9 1.388(6) . ? C8 C9 1.381(7) . ? C8 N1 1.464(8) . ? C9 C10 1.379(8) . ? C10 C11 1.384(8) . ? C10 C15 1.514(7) . ? C11 C12 1.370(8) . ? C13 O1 1.255(6) . ? C13 O2 1.260(6) . ? C14 O4 1.249(6) . ? C14 O3 1.266(6) . ? C14 Ce1 2.875(5) 8_566 ? C15 O7 1.244(6) . ? C15 O8 1.252(7) . ? C16 O10 1.186(9) . ? C16 N2 1.262(10) . ? C17 N2 1.447(10) . ? C18 N2 1.436(10) . ? C19 O11 1.227(8) . ? C19 N3 1.314(8) . ? C20 N3 1.437(9) . ? C21 N3 1.462(9) . ? N1 O5 1.215(7) . ? N1 O6 1.222(7) . ? O2 Ce1 2.446(4) 7_566 ? O3 Ce1 2.506(4) 8_566 ? O4 Ce1 2.570(4) 8_566 ? O7 Ce1 2.483(4) 6_575 ? O8 Ce1 2.470(4) 4 ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag O2 Ce1 O8 69.04(13) 7_566 4_545 ? O2 Ce1 O7 79.99(13) 7_566 6_576 ? O8 Ce1 O7 132.43(13) 4_545 6_576 ? O2 Ce1 O11 75.45(15) 7_566 . ? O8 Ce1 O11 127.58(16) 4_545 . ? O7 Ce1 O11 74.09(15) 6_576 . ? O2 Ce1 O1 123.03(12) 7_566 . ? O8 Ce1 O1 91.09(15) 4_545 . ? O7 Ce1 O1 76.24(14) 6_576 . ? O11 Ce1 O1 141.14(16) . . ? O2 Ce1 O10 145.90(17) 7_566 . ? O8 Ce1 O10 143.60(16) 4_545 . ? O7 Ce1 O10 78.00(16) 6_576 . ? O11 Ce1 O10 73.7(2) . . ? O1 Ce1 O10 76.09(19) . . ? O2 Ce1 O3 101.23(13) 7_566 8_465 ? O8 Ce1 O3 77.18(14) 4_545 8_465 ? O7 Ce1 O3 145.89(12) 6_576 8_465 ? O11 Ce1 O3 73.33(15) . 8_465 ? O1 Ce1 O3 126.49(13) . 8_465 ? O10 Ce1 O3 83.43(17) . 8_465 ? O2 Ce1 O4 135.36(12) 7_566 8_465 ? O8 Ce1 O4 70.49(13) 4_545 8_465 ? O7 Ce1 O4 143.51(12) 6_576 8_465 ? O11 Ce1 O4 117.44(15) . 8_465 ? O1 Ce1 O4 75.35(12) . 8_465 ? O10 Ce1 O4 73.32(16) . 8_465 ? O3 Ce1 O4 51.38(12) 8_465 8_465 ? O2 Ce1 O2 74.57(12) 7_566 . ? O8 Ce1 O2 70.53(13) 4_545 . ? O7 Ce1 O2 66.88(12) 6_576 . ? O11 Ce1 O2 133.93(14) . . ? O1 Ce1 O2 48.51(12) . . ? O10 Ce1 O2 118.85(18) . . ? O3 Ce1 O2 146.78(12) 8_465 . ? O4 Ce1 O2 108.50(11) 8_465 . ? O2 Ce1 C14 117.71(14) 7_566 8_465 ? O8 Ce1 C14 68.51(15) 4_545 8_465 ? O7 Ce1 C14 158.41(14) 6_576 8_465 ? O11 Ce1 C14 97.44(16) . 8_465 ? O1 Ce1 C14 101.09(14) . 8_465 ? O10 Ce1 C14 80.56(17) . 8_465 ? O3 Ce1 C14 26.08(13) 8_465 8_465 ? O4 Ce1 C14 25.76(13) 8_465 8_465 ? O2 Ce1 C14 127.42(13) . 8_465 ? O2 Ce1 C13 98.97(13) 7_566 . ? O8 Ce1 C13 82.72(15) 4_545 . ? O7 Ce1 C13 67.11(14) 6_576 . ? O11 Ce1 C13 141.16(15) . . ? O1 Ce1 C13 24.10(13) . . ? O10 Ce1 C13 96.07(19) . . ? O3 Ce1 C13 143.99(13) 8_465 . ? O4 Ce1 C13 93.81(13) 8_465 . ? O2 Ce1 C13 24.71(12) . . ? C14 Ce1 C13 118.13(14) 8_465 . ? C6 C1 C2 119.7(5) . . ? C6 C1 C13 117.6(5) . . ? C2 C1 C13 122.7(4) . . ? C1 C2 C3 119.7(5) . . ? C4 C3 C2 120.0(5) . . ? C4 C3 C14 119.8(5) . . ? C2 C3 C14 120.2(4) . . ? C5 C4 C3 119.2(5) . . ? C4 C5 C6 121.7(5) . . ? C4 C5 O9 115.9(5) . . ? C6 C5 O9 122.4(5) . . ? C5 C6 C1 119.7(5) . . ? C12 C7 C8 119.1(5) . . ? C12 C7 O9 117.6(5) . . ? C8 C7 O9 123.3(5) . . ? C9 C8 C7 120.1(5) . . ? C9 C8 N1 117.3(5) . . ? C7 C8 N1 122.6(5) . . ? C10 C9 C8 120.5(5) . . ? C9 C10 C11 119.1(5) . . ? C9 C10 C15 120.4(5) . . ? C11 C10 C15 120.5(5) . . ? C12 C11 C10 120.6(6) . . ? C11 C12 C7 120.5(5) . . ? O1 C13 O2 121.4(5) . . ? O1 C13 C1 118.2(5) . . ? O2 C13 C1 120.3(5) . . ? O1 C13 Ce1 54.1(3) . . ? O2 C13 Ce1 68.5(3) . . ? C1 C13 Ce1 166.3(4) . . ? O4 C14 O3 122.1(5) . . ? O4 C14 C3 118.8(4) . . ? O3 C14 C3 119.1(5) . . ? O4 C14 Ce1 63.3(3) . 8_566 ? O3 C14 Ce1 60.5(3) . 8_566 ? C3 C14 Ce1 165.8(4) . 8_566 ? O7 C15 O8 126.6(5) . . ? O7 C15 C10 117.2(5) . . ? O8 C15 C10 116.1(5) . . ? O10 C16 N2 131.8(9) . . ? O11 C19 N3 124.2(7) . . ? O5 N1 O6 123.2(6) . . ? O5 N1 C8 119.1(6) . . ? O6 N1 C8 117.7(5) . . ? C16 N2 C18 117.8(7) . . ? C16 N2 C17 127.3(8) . . ? C18 N2 C17 112.5(6) . . ? C19 N3 C20 121.2(6) . . ? C19 N3 C21 121.2(6) . . ? C20 N3 C21 117.5(5) . . ? C13 O1 Ce1 101.8(3) . . ? C13 O2 Ce1 164.8(3) . 7_566 ? C13 O2 Ce1 86.7(3) . . ? Ce1 O2 Ce1 105.43(12) 7_566 . ? C14 O3 Ce1 93.5(3) . 8_566 ? C14 O4 Ce1 90.9(3) . 8_566 ? C15 O7 Ce1 135.3(4) . 6_575 ? C15 O8 Ce1 142.2(4) . 4 ? C7 O9 C5 114.7(4) . . ? C16 O10 Ce1 136.9(6) . . ? C19 O11 Ce1 140.4(5) . . ? _diffrn_measured_fraction_theta_max 0.996 _diffrn_reflns_theta_full 26.16 _diffrn_measured_fraction_theta_full 0.996 _refine_diff_density_max 2.850 _refine_diff_density_min -2.526 _refine_diff_density_rms 0.156 data_3 _database_code_depnum_ccdc_archive 'CCDC 857004' #TrackingRef '- 1-12 and 7.CIF' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point 'not measured' _chemical_formula_moiety 'C21 H20.50 N3 O11.25 Pr' _chemical_formula_sum 'C21 H20.50 N3 O11.25 Pr' _chemical_formula_weight 635.81 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Pr Pr -0.2180 2.8214 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Monoclinic _symmetry_space_group_name_H-M C2/c loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y, -z+1/2' 'x+1/2, y+1/2, z' '-x+1/2, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y, z-1/2' '-x+1/2, -y+1/2, -z' 'x+1/2, -y+1/2, z-1/2' _cell_length_a 23.7046(11) _cell_length_b 15.7987(7) _cell_length_c 16.2398(14) _cell_angle_alpha 90.00 _cell_angle_beta 124.2040(10) _cell_angle_gamma 90.00 _cell_volume 5029.9(5) _cell_formula_units_Z 8 _cell_measurement_temperature 185(2) _cell_measurement_reflns_used 4989 _cell_measurement_theta_min 1.66 _cell_measurement_theta_max 26.10 _exptl_crystal_description rod _exptl_crystal_colour 'light yellow' _exptl_crystal_size_max 0.26 _exptl_crystal_size_mid 0.21 _exptl_crystal_size_min 0.19 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.679 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 2532 _exptl_absorpt_coefficient_mu 2.001 _exptl_absorpt_correction_type empirical _exptl_absorpt_correction_T_min 0.6243 _exptl_absorpt_correction_T_max 0.7024 _exptl_absorpt_process_details SADABS _exptl_special_details ; ? ; _diffrn_ambient_temperature 185(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'CCD area detector' _diffrn_measurement_method 'phi and omega scans' _diffrn_detector_area_resol_mean 9.00cm _diffrn_standards_number none _diffrn_standards_interval_count none _diffrn_standards_interval_time none _diffrn_standards_decay_% none _diffrn_reflns_number 13801 _diffrn_reflns_av_R_equivalents 0.0245 _diffrn_reflns_av_sigmaI/netI 0.0288 _diffrn_reflns_limit_h_min -29 _diffrn_reflns_limit_h_max 21 _diffrn_reflns_limit_k_min -12 _diffrn_reflns_limit_k_max 19 _diffrn_reflns_limit_l_min -20 _diffrn_reflns_limit_l_max 20 _diffrn_reflns_theta_min 1.66 _diffrn_reflns_theta_max 26.10 _reflns_number_total 4989 _reflns_number_gt 4542 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SMART' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics SHELXP-97 _computing_publication_material SHELXTL _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0321P)^2^+41.0532P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 4989 _refine_ls_number_parameters 298 _refine_ls_number_restraints 6 _refine_ls_R_factor_all 0.0377 _refine_ls_R_factor_gt 0.0345 _refine_ls_wR_factor_ref 0.0832 _refine_ls_wR_factor_gt 0.0809 _refine_ls_goodness_of_fit_ref 1.043 _refine_ls_restrained_S_all 1.043 _refine_ls_shift/su_max 0.001 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group Pr1 Pr 0.189154(9) 0.170699(12) 0.378545(14) 0.01509(8) Uani 1 1 d . . . C1 C 0.3722(2) 0.0369(2) 0.6775(3) 0.0216(8) Uani 1 1 d . . . C2 C 0.3601(2) -0.0450(2) 0.6409(3) 0.0228(8) Uani 1 1 d . . . H2A H 0.3234 -0.0562 0.5741 0.027 Uiso 1 1 calc R . . C3 C 0.4017(2) -0.1108(3) 0.7020(3) 0.0244(8) Uani 1 1 d . . . C4 C 0.4559(2) -0.0947(3) 0.7999(3) 0.0250(9) Uani 1 1 d . . . C5 C 0.4689(2) -0.0120(3) 0.8347(3) 0.0305(10) Uani 1 1 d . . . H5A H 0.5067 -0.0002 0.9005 0.037 Uiso 1 1 calc R . . C6 C 0.4274(2) 0.0531(3) 0.7743(3) 0.0292(9) Uani 1 1 d . . . H6A H 0.4366 0.1095 0.7989 0.035 Uiso 1 1 calc R . . C7 C 0.4820(2) -0.1903(3) 0.9271(3) 0.0233(8) Uani 1 1 d . . . C8 C 0.4163(2) -0.1870(3) 0.9042(3) 0.0236(8) Uani 1 1 d . . . H8A H 0.3809 -0.1610 0.8443 0.028 Uiso 1 1 calc R . . C9 C 0.40234(19) -0.2221(2) 0.9694(3) 0.0205(8) Uani 1 1 d . . . C10 C 0.45478(19) -0.2581(2) 1.0588(3) 0.0199(8) Uani 1 1 d . . . H10A H 0.4457 -0.2802 1.1047 0.024 Uiso 1 1 calc R . . C11 C 0.52072(19) -0.2613(2) 1.0805(3) 0.0188(8) Uani 1 1 d . . . C12 C 0.53449(19) -0.2276(2) 1.0142(3) 0.0197(8) Uani 1 1 d . . . H12A H 0.5792 -0.2303 1.0285 0.024 Uiso 1 1 calc R . . C13 C 0.3242(2) 0.1076(3) 0.6132(3) 0.0227(8) Uani 1 1 d . . . C14 C 0.32988(19) -0.2199(2) 0.9392(3) 0.0212(8) Uani 1 1 d . . . C15 C 0.57806(19) -0.2987(2) 1.1767(3) 0.0192(8) Uani 1 1 d . . . C19 C 0.0722(3) 0.0425(3) 0.3888(4) 0.0484(5) Uani 1 1 d . A . H19A H 0.0345 0.0769 0.3427 0.058 Uiso 1 1 calc R . . C20 C -0.0105(3) -0.0591(3) 0.3699(4) 0.0484(5) Uani 1 1 d . . . H20A H -0.0423 -0.0140 0.3284 0.073 Uiso 1 1 calc R . . H20B H -0.0163 -0.0728 0.4236 0.073 Uiso 1 1 calc R . . H20C H -0.0197 -0.1096 0.3290 0.073 Uiso 1 1 calc R . . C21 C 0.1146(3) -0.0886(3) 0.4792(4) 0.0484(5) Uani 1 1 d . . . H21A H 0.1585 -0.0619 0.5026 0.073 Uiso 1 1 calc R . . H21B H 0.1101 -0.1409 0.4434 0.073 Uiso 1 1 calc R . . H21C H 0.1125 -0.1019 0.5364 0.073 Uiso 1 1 calc R . . N1 N 0.3855(2) -0.1959(2) 0.6596(3) 0.0348(9) Uani 1 1 d . . . N2 N 0.2293(2) -0.0864(3) 0.2843(3) 0.0508(7) Uani 1 1 d . . . N3 N 0.0593(2) -0.0308(3) 0.4125(4) 0.0484(5) Uani 1 1 d . . . O1 O 0.33316(17) 0.17715(17) 0.6564(2) 0.0313(7) Uani 1 1 d . . . O2 O 0.27958(14) 0.09058(18) 0.5240(2) 0.0267(6) Uani 1 1 d . . . O3 O 0.3490(2) -0.2023(2) 0.5685(3) 0.0542(10) Uani 1 1 d . . . O4 O 0.4082(3) -0.2569(2) 0.7146(3) 0.0639(13) Uani 1 1 d . . . O5 O 0.28734(14) -0.1782(2) 0.8631(2) 0.0298(7) Uani 1 1 d . . . O6 O 0.31266(14) -0.25944(18) 0.9895(2) 0.0230(6) Uani 1 1 d . . . O7 O 0.56610(14) -0.32467(18) 1.2393(2) 0.0258(6) Uani 1 1 d . . . O8 O 0.63661(13) -0.30175(19) 1.19352(19) 0.0236(6) Uani 1 1 d . . . O9 O 0.49926(15) -0.1572(2) 0.8646(2) 0.0333(7) Uani 1 1 d . . . O10 O 0.1868(2) 0.0334(2) 0.3032(3) 0.0508(7) Uani 1 1 d . . . O11 O 0.12983(19) 0.0695(2) 0.4222(3) 0.0484(5) Uani 1 1 d . . . C16 C 0.2103(6) -0.0399(8) 0.3307(10) 0.0508(7) Uani 0.50 1 d P A 1 H16A H 0.2143 -0.0625 0.3880 0.061 Uiso 0.50 1 calc PR A 1 C16' C 0.2333(7) -0.0144(8) 0.3318(10) 0.0508(7) Uani 0.50 1 d P A 2 H16B H 0.2756 -0.0008 0.3917 0.061 Uiso 0.50 1 calc PR A 2 C17 C 0.1999(6) -0.0697(8) 0.1753(9) 0.0508(7) Uani 0.50 1 d P A 1 H17A H 0.1932 -0.0087 0.1623 0.076 Uiso 0.50 1 calc PR A 1 H17B H 0.1561 -0.0990 0.1338 0.076 Uiso 0.50 1 calc PR A 1 H17C H 0.2316 -0.0907 0.1593 0.076 Uiso 0.50 1 calc PR A 1 C17' C 0.1768(6) -0.0987(8) 0.1816(9) 0.0508(7) Uani 0.50 1 d P A 2 H17D H 0.1612 -0.0436 0.1484 0.076 Uiso 0.50 1 calc PR A 2 H17E H 0.1385 -0.1288 0.1756 0.076 Uiso 0.50 1 calc PR A 2 H17F H 0.1947 -0.1322 0.1503 0.076 Uiso 0.50 1 calc PR A 2 C18 C 0.2453(8) -0.1817(9) 0.3239(11) 0.0508(7) Uani 0.40 1 d P A 1 H18A H 0.2035 -0.2086 0.3100 0.076 Uiso 0.40 1 calc PR A 1 H18B H 0.2799 -0.1819 0.3959 0.076 Uiso 0.40 1 calc PR A 1 H18C H 0.2625 -0.2132 0.2903 0.076 Uiso 0.40 1 calc PR A 1 C18' C 0.3007(11) -0.1257(13) 0.3327(15) 0.0508(7) Uani 0.30 1 d P A 2 H18D H 0.3318 -0.0835 0.3349 0.076 Uiso 0.30 1 calc PR A 2 H18E H 0.2979 -0.1746 0.2935 0.076 Uiso 0.30 1 calc PR A 2 H18F H 0.3177 -0.1440 0.4006 0.076 Uiso 0.30 1 calc PR A 2 C18" C 0.2711(12) -0.1604(13) 0.3136(16) 0.0508(7) Uani 0.30 1 d P A 3 H18G H 0.3100 -0.1492 0.3092 0.076 Uiso 0.30 1 calc PR A 3 H18H H 0.2443 -0.2075 0.2694 0.076 Uiso 0.30 1 calc PR A 3 H18I H 0.2878 -0.1752 0.3823 0.076 Uiso 0.30 1 calc PR A 3 O1W O 0.2484(13) -0.3453(16) 0.3389(19) 0.101(7) Uani 0.25 1 d PU . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 Pr1 0.01178(11) 0.01619(12) 0.01170(11) 0.00044(7) 0.00319(9) 0.00123(7) C1 0.0215(19) 0.0207(19) 0.0190(19) 0.0054(15) 0.0092(17) 0.0047(15) C2 0.023(2) 0.023(2) 0.0198(19) 0.0047(15) 0.0101(17) 0.0045(16) C3 0.027(2) 0.022(2) 0.029(2) 0.0064(17) 0.0191(18) 0.0052(16) C4 0.023(2) 0.032(2) 0.025(2) 0.0171(17) 0.0166(18) 0.0119(17) C5 0.024(2) 0.041(3) 0.0173(19) 0.0064(18) 0.0059(17) 0.0071(19) C6 0.029(2) 0.026(2) 0.023(2) 0.0006(17) 0.0097(19) 0.0020(17) C7 0.022(2) 0.026(2) 0.023(2) 0.0093(16) 0.0134(17) 0.0076(16) C8 0.0194(19) 0.028(2) 0.0197(19) 0.0092(16) 0.0088(17) 0.0078(16) C9 0.0189(19) 0.0220(19) 0.0187(18) 0.0010(15) 0.0094(16) 0.0002(15) C10 0.0190(18) 0.024(2) 0.0159(17) 0.0004(15) 0.0092(16) -0.0024(15) C11 0.0178(18) 0.0194(18) 0.0154(17) 0.0005(14) 0.0070(15) 0.0015(14) C12 0.0153(18) 0.0210(19) 0.0217(19) 0.0037(15) 0.0097(16) 0.0033(14) C13 0.023(2) 0.021(2) 0.0182(19) 0.0054(15) 0.0080(17) 0.0034(16) C14 0.0194(19) 0.023(2) 0.0177(18) -0.0011(15) 0.0085(16) -0.0004(15) C15 0.0172(18) 0.0196(18) 0.0148(17) -0.0020(15) 0.0053(15) -0.0016(15) C19 0.0460(12) 0.0398(11) 0.0544(13) 0.0070(10) 0.0251(11) -0.0104(9) C20 0.0460(12) 0.0398(11) 0.0544(13) 0.0070(10) 0.0251(11) -0.0104(9) C21 0.0460(12) 0.0398(11) 0.0544(13) 0.0070(10) 0.0251(11) -0.0104(9) N1 0.042(2) 0.0243(19) 0.044(2) 0.0067(17) 0.028(2) 0.0085(17) N2 0.0556(17) 0.0395(14) 0.0488(14) -0.0085(11) 0.0241(13) 0.0122(11) N3 0.0460(12) 0.0398(11) 0.0544(13) 0.0070(10) 0.0251(11) -0.0104(9) O1 0.0409(18) 0.0184(15) 0.0205(14) 0.0028(11) 0.0086(14) 0.0073(12) O2 0.0244(15) 0.0213(14) 0.0194(14) 0.0027(11) 0.0032(12) 0.0036(11) O3 0.058(2) 0.035(2) 0.045(2) -0.0058(17) 0.013(2) 0.0041(18) O4 0.108(4) 0.0275(19) 0.059(3) 0.0141(18) 0.049(3) 0.019(2) O5 0.0154(14) 0.0487(19) 0.0223(15) 0.0125(13) 0.0088(12) 0.0067(12) O6 0.0216(14) 0.0268(15) 0.0232(14) 0.0013(11) 0.0142(12) 0.0004(11) O7 0.0156(13) 0.0370(17) 0.0169(13) 0.0084(12) 0.0042(11) -0.0003(12) O8 0.0160(13) 0.0343(16) 0.0166(13) 0.0033(12) 0.0068(11) 0.0045(11) O9 0.0267(16) 0.0451(19) 0.0367(17) 0.0283(15) 0.0230(14) 0.0206(14) O10 0.0556(17) 0.0395(14) 0.0488(14) -0.0085(11) 0.0241(13) 0.0122(11) O11 0.0460(12) 0.0398(11) 0.0544(13) 0.0070(10) 0.0251(11) -0.0104(9) C16 0.0556(17) 0.0395(14) 0.0488(14) -0.0085(11) 0.0241(13) 0.0122(11) C16' 0.0556(17) 0.0395(14) 0.0488(14) -0.0085(11) 0.0241(13) 0.0122(11) C17 0.0556(17) 0.0395(14) 0.0488(14) -0.0085(11) 0.0241(13) 0.0122(11) C17' 0.0556(17) 0.0395(14) 0.0488(14) -0.0085(11) 0.0241(13) 0.0122(11) C18 0.0556(17) 0.0395(14) 0.0488(14) -0.0085(11) 0.0241(13) 0.0122(11) C18' 0.0556(17) 0.0395(14) 0.0488(14) -0.0085(11) 0.0241(13) 0.0122(11) C18" 0.0556(17) 0.0395(14) 0.0488(14) -0.0085(11) 0.0241(13) 0.0122(11) O1W 0.097(11) 0.116(11) 0.099(11) 0.026(8) 0.062(8) -0.013(8) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag Pr1 O6 2.432(3) 4_556 ? Pr1 O1 2.458(3) 7_556 ? Pr1 O2 2.466(3) . ? Pr1 O10 2.476(3) . ? Pr1 O5 2.480(3) 6 ? Pr1 O11 2.481(3) . ? Pr1 O7 2.492(3) 3_454 ? Pr1 O8 2.562(3) 3_454 ? Pr1 O6 2.802(3) 6 ? Pr1 C15 2.865(4) 3_454 ? Pr1 C14 3.001(4) 6 ? C1 C2 1.384(6) . ? C1 C6 1.391(6) . ? C1 C13 1.516(5) . ? C2 C3 1.392(5) . ? C3 C4 1.395(6) . ? C3 N1 1.461(6) . ? C4 O9 1.387(5) . ? C4 C5 1.388(6) . ? C5 C6 1.380(6) . ? C7 C8 1.384(6) . ? C7 C12 1.384(5) . ? C7 O9 1.392(5) . ? C8 C9 1.389(6) . ? C9 C10 1.396(5) . ? C9 C14 1.499(5) . ? C10 C11 1.397(5) . ? C11 C12 1.395(5) . ? C11 C15 1.500(5) . ? C13 O2 1.252(5) . ? C13 O1 1.256(5) . ? C14 O5 1.255(5) . ? C14 O6 1.265(5) . ? C14 Pr1 3.001(4) 6_556 ? C15 O8 1.256(5) . ? C15 O7 1.267(5) . ? C15 Pr1 2.865(4) 3_546 ? C19 O11 1.229(6) . ? C19 N3 1.310(6) . ? C20 N3 1.458(7) . ? C21 N3 1.460(7) . ? N1 O4 1.215(5) . ? N1 O3 1.228(5) . ? N2 C16 1.300(13) . ? N2 C16' 1.348(12) . ? N2 C17' 1.426(12) . ? N2 C18" 1.430(19) . ? N2 C17 1.518(13) . ? N2 C18' 1.540(19) . ? N2 C18 1.598(15) . ? O1 Pr1 2.458(3) 7_556 ? O5 Pr1 2.480(3) 6_556 ? O6 Pr1 2.432(3) 4_546 ? O6 Pr1 2.802(3) 6_556 ? O7 Pr1 2.492(3) 3_546 ? O8 Pr1 2.562(3) 3_546 ? O10 C16' 1.192(12) . ? O10 C16 1.253(12) . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag O6 Pr1 O1 69.61(10) 4_556 7_556 ? O6 Pr1 O2 79.96(9) 4_556 . ? O1 Pr1 O2 132.95(10) 7_556 . ? O6 Pr1 O10 145.74(12) 4_556 . ? O1 Pr1 O10 143.18(12) 7_556 . ? O2 Pr1 O10 77.84(11) . . ? O6 Pr1 O5 123.34(9) 4_556 6 ? O1 Pr1 O5 91.26(11) 7_556 6 ? O2 Pr1 O5 76.21(10) . 6 ? O10 Pr1 O5 75.74(12) . 6 ? O6 Pr1 O11 75.34(11) 4_556 . ? O1 Pr1 O11 127.80(12) 7_556 . ? O2 Pr1 O11 73.91(11) . . ? O10 Pr1 O11 73.63(14) . . ? O5 Pr1 O11 140.79(12) 6 . ? O6 Pr1 O7 101.23(9) 4_556 3_454 ? O1 Pr1 O7 76.80(10) 7_556 3_454 ? O2 Pr1 O7 145.87(9) . 3_454 ? O10 Pr1 O7 83.56(11) . 3_454 ? O5 Pr1 O7 126.37(10) 6 3_454 ? O11 Pr1 O7 73.50(11) . 3_454 ? O6 Pr1 O8 135.93(9) 4_556 3_454 ? O1 Pr1 O8 70.32(10) 7_556 3_454 ? O2 Pr1 O8 142.96(9) . 3_454 ? O10 Pr1 O8 73.03(11) . 3_454 ? O5 Pr1 O8 74.83(9) 6 3_454 ? O11 Pr1 O8 117.69(11) . 3_454 ? O7 Pr1 O8 51.78(9) 3_454 3_454 ? O6 Pr1 O6 74.68(9) 4_556 6 ? O1 Pr1 O6 70.77(10) 7_556 6 ? O2 Pr1 O6 67.01(9) . 6 ? O10 Pr1 O6 118.76(11) . 6 ? O5 Pr1 O6 48.74(9) 6 6 ? O11 Pr1 O6 133.91(10) . 6 ? O7 Pr1 O6 146.68(9) 3_454 6 ? O8 Pr1 O6 108.23(8) 3_454 6 ? O6 Pr1 C15 118.10(10) 4_556 3_454 ? O1 Pr1 C15 68.32(10) 7_556 3_454 ? O2 Pr1 C15 158.02(10) . 3_454 ? O10 Pr1 C15 80.32(12) . 3_454 ? O5 Pr1 C15 100.82(10) 6 3_454 ? O11 Pr1 C15 97.56(12) . 3_454 ? O7 Pr1 C15 26.19(10) 3_454 3_454 ? O8 Pr1 C15 26.00(10) 3_454 3_454 ? O6 Pr1 C15 127.41(10) 6 3_454 ? O6 Pr1 C14 99.21(10) 4_556 6 ? O1 Pr1 C14 82.98(11) 7_556 6 ? O2 Pr1 C14 67.12(10) . 6 ? O10 Pr1 C14 95.79(12) . 6 ? O5 Pr1 C14 24.17(10) 6 6 ? O11 Pr1 C14 140.97(11) . 6 ? O7 Pr1 C14 143.92(10) 3_454 6 ? O8 Pr1 C14 93.38(9) 3_454 6 ? O6 Pr1 C14 24.88(9) 6 6 ? C15 Pr1 C14 117.99(11) 3_454 6 ? C2 C1 C6 119.6(4) . . ? C2 C1 C13 119.9(3) . . ? C6 C1 C13 120.5(4) . . ? C1 C2 C3 119.9(4) . . ? C2 C3 C4 120.4(4) . . ? C2 C3 N1 117.3(4) . . ? C4 C3 N1 122.3(4) . . ? O9 C4 C5 117.5(4) . . ? O9 C4 C3 123.4(4) . . ? C5 C4 C3 119.1(4) . . ? C6 C5 C4 120.4(4) . . ? C5 C6 C1 120.5(4) . . ? C8 C7 C12 121.3(4) . . ? C8 C7 O9 122.5(3) . . ? C12 C7 O9 116.1(3) . . ? C7 C8 C9 119.6(4) . . ? C8 C9 C10 120.1(4) . . ? C8 C9 C14 117.5(3) . . ? C10 C9 C14 122.5(3) . . ? C9 C10 C11 119.5(4) . . ? C12 C11 C10 120.4(3) . . ? C12 C11 C15 119.1(3) . . ? C10 C11 C15 120.5(3) . . ? C7 C12 C11 119.0(4) . . ? O2 C13 O1 127.0(4) . . ? O2 C13 C1 117.2(4) . . ? O1 C13 C1 115.7(3) . . ? O5 C14 O6 121.5(4) . . ? O5 C14 C9 118.2(3) . . ? O6 C14 C9 120.2(3) . . ? O5 C14 Pr1 54.0(2) . 6_556 ? O6 C14 Pr1 68.7(2) . 6_556 ? C9 C14 Pr1 166.4(3) . 6_556 ? O8 C15 O7 122.1(3) . . ? O8 C15 C11 119.0(3) . . ? O7 C15 C11 118.9(3) . . ? O8 C15 Pr1 63.40(19) . 3_546 ? O7 C15 Pr1 60.27(19) . 3_546 ? C11 C15 Pr1 166.0(3) . 3_546 ? O11 C19 N3 124.3(5) . . ? O4 N1 O3 122.8(4) . . ? O4 N1 C3 119.5(4) . . ? O3 N1 C3 117.7(4) . . ? C16 N2 C16' 29.2(7) . . ? C16 N2 C17' 113.3(8) . . ? C16' N2 C17' 121.3(8) . . ? C16 N2 C18" 132.1(11) . . ? C16' N2 C18" 133.4(11) . . ? C17' N2 C18" 105.3(10) . . ? C16 N2 C17 119.8(8) . . ? C16' N2 C17 111.1(8) . . ? C17' N2 C17 29.9(6) . . ? C18" N2 C17 107.9(10) . . ? C16 N2 C18' 124.8(10) . . ? C16' N2 C18' 110.2(10) . . ? C17' N2 C18' 121.9(9) . . ? C18" N2 C18' 31.0(10) . . ? C17 N2 C18' 108.5(10) . . ? C16 N2 C18 112.4(9) . . ? C16' N2 C18 129.9(8) . . ? C17' N2 C18 101.3(8) . . ? C18" N2 C18 29.7(10) . . ? C17 N2 C18 118.9(7) . . ? C18' N2 C18 58.0(10) . . ? C19 N3 C20 121.4(5) . . ? C19 N3 C21 120.7(5) . . ? C20 N3 C21 117.9(4) . . ? C13 O1 Pr1 141.2(3) . 7_556 ? C13 O2 Pr1 135.4(3) . . ? C14 O5 Pr1 101.9(2) . 6_556 ? C14 O6 Pr1 164.9(3) . 4_546 ? C14 O6 Pr1 86.4(2) . 6_556 ? Pr1 O6 Pr1 105.32(9) 4_546 6_556 ? C15 O7 Pr1 93.5(2) . 3_546 ? C15 O8 Pr1 90.6(2) . 3_546 ? C4 O9 C7 115.0(3) . . ? C16' O10 C16 31.7(8) . . ? C16' O10 Pr1 127.1(7) . . ? C16 O10 Pr1 138.7(6) . . ? C19 O11 Pr1 140.0(4) . . ? O10 C16 N2 123.0(12) . . ? O10 C16' N2 124.0(11) . . ? _diffrn_measured_fraction_theta_max 0.999 _diffrn_reflns_theta_full 26.10 _diffrn_measured_fraction_theta_full 0.999 _refine_diff_density_max 1.830 _refine_diff_density_min -2.339 _refine_diff_density_rms 0.114 data_4 _database_code_depnum_ccdc_archive 'CCDC 857005' #TrackingRef '- 1-12 and 7.CIF' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point 'not measured' _chemical_formula_moiety 'C21 H20.50 N3 Nd O11.25' _chemical_formula_sum 'C21 H20.50 N3 Nd O11.25' _chemical_formula_weight 639.14 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Nd Nd -0.1943 3.0179 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Monoclinic _symmetry_space_group_name_H-M C2/c loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y, -z+1/2' 'x+1/2, y+1/2, z' '-x+1/2, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y, z-1/2' '-x+1/2, -y+1/2, -z' 'x+1/2, -y+1/2, z-1/2' _cell_length_a 23.6490(11) _cell_length_b 15.7654(8) _cell_length_c 16.2182(8) _cell_angle_alpha 90.00 _cell_angle_beta 124.2720(10) _cell_angle_gamma 90.00 _cell_volume 4996.9(4) _cell_formula_units_Z 8 _cell_measurement_temperature 185(2) _cell_measurement_reflns_used 4925 _cell_measurement_theta_min 1.66 _cell_measurement_theta_max 26.08 _exptl_crystal_description rod _exptl_crystal_colour 'light yellow' _exptl_crystal_size_max 0.29 _exptl_crystal_size_mid 0.22 _exptl_crystal_size_min 0.20 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.699 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 2540 _exptl_absorpt_coefficient_mu 2.142 _exptl_absorpt_correction_type empirical _exptl_absorpt_correction_T_min 0.5755 _exptl_absorpt_correction_T_max 0.6740 _exptl_absorpt_process_details SADABS _exptl_special_details ; ? ; _diffrn_ambient_temperature 185(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'CCD area detector' _diffrn_measurement_method 'phi and omega scans' _diffrn_detector_area_resol_mean 9.00cm _diffrn_standards_number none _diffrn_standards_interval_count none _diffrn_standards_interval_time none _diffrn_standards_decay_% none _diffrn_reflns_number 13686 _diffrn_reflns_av_R_equivalents 0.0430 _diffrn_reflns_av_sigmaI/netI 0.0515 _diffrn_reflns_limit_h_min -29 _diffrn_reflns_limit_h_max 29 _diffrn_reflns_limit_k_min -19 _diffrn_reflns_limit_k_max 17 _diffrn_reflns_limit_l_min -20 _diffrn_reflns_limit_l_max 16 _diffrn_reflns_theta_min 1.66 _diffrn_reflns_theta_max 26.08 _reflns_number_total 4925 _reflns_number_gt 4019 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SMART' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics SHELXP-97 _computing_publication_material SHELXTL _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0366P)^2^+32.5737P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 4925 _refine_ls_number_parameters 295 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0513 _refine_ls_R_factor_gt 0.0398 _refine_ls_wR_factor_ref 0.0970 _refine_ls_wR_factor_gt 0.0902 _refine_ls_goodness_of_fit_ref 1.046 _refine_ls_restrained_S_all 1.046 _refine_ls_shift/su_max 0.001 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group Nd1 Nd 0.189307(13) 0.171289(16) 0.378626(19) 0.01587(9) Uani 1 1 d . . . C1 C 0.4021(2) 0.2226(3) 0.4697(4) 0.0205(11) Uani 1 1 d . . . C2 C 0.4162(3) 0.1876(3) 0.4041(4) 0.0251(12) Uani 1 1 d . . . H2A H 0.3807 0.1621 0.3437 0.030 Uiso 1 1 calc R . . C3 C 0.4823(3) 0.1904(3) 0.4277(4) 0.0237(11) Uani 1 1 d . . . C4 C 0.5343(3) 0.2278(3) 0.5146(4) 0.0219(11) Uani 1 1 d . . . H4A H 0.5792 0.2306 0.5290 0.026 Uiso 1 1 calc R . . C5 C 0.5207(2) 0.2615(3) 0.5814(4) 0.0183(10) Uani 1 1 d . . . C6 C 0.4547(2) 0.2582(3) 0.5593(4) 0.0213(11) Uani 1 1 d . . . H6A H 0.4456 0.2801 0.6052 0.026 Uiso 1 1 calc R . . C7 C 0.4548(3) 0.0947(4) 0.2992(4) 0.0292(13) Uani 1 1 d . . . C8 C 0.4014(3) 0.1110(3) 0.2012(4) 0.0244(12) Uani 1 1 d . . . C9 C 0.3599(3) 0.0449(3) 0.1406(4) 0.0256(12) Uani 1 1 d . . . H9A H 0.3230 0.0562 0.0738 0.031 Uiso 1 1 calc R . . C10 C 0.3716(3) -0.0373(3) 0.1767(4) 0.0232(11) Uani 1 1 d . . . C11 C 0.4272(3) -0.0528(4) 0.2737(4) 0.0327(13) Uani 1 1 d . . . H11A H 0.4368 -0.1092 0.2986 0.039 Uiso 1 1 calc R . . C12 C 0.4686(3) 0.0126(4) 0.3342(4) 0.0320(13) Uani 1 1 d . . . H12A H 0.5066 0.0009 0.4001 0.038 Uiso 1 1 calc R . . C13 C 0.3294(2) 0.2208(3) 0.4392(4) 0.0200(11) Uani 1 1 d . . . C14 C 0.3244(3) -0.1078(3) 0.1131(4) 0.0238(12) Uani 1 1 d . . . C15 C 0.5782(2) 0.2981(3) 0.6774(4) 0.0187(10) Uani 1 1 d . . . C19 C 0.0733(4) 0.0428(4) 0.3889(6) 0.0496(7) Uani 1 1 d . A . H19A H 0.0355 0.0770 0.3419 0.060 Uiso 1 1 calc R . . C20 C -0.0099(3) -0.0590(4) 0.3711(6) 0.0496(7) Uani 1 1 d . . . H20A H -0.0421 -0.0145 0.3281 0.074 Uiso 1 1 calc R . . H20B H -0.0158 -0.0714 0.4250 0.074 Uiso 1 1 calc R . . H20C H -0.0188 -0.1104 0.3316 0.074 Uiso 1 1 calc R . . C21 C 0.1155(3) -0.0882(4) 0.4809(6) 0.0496(7) Uani 1 1 d . . . H21A H 0.1596 -0.0619 0.5044 0.074 Uiso 1 1 calc R . . H21B H 0.1107 -0.1409 0.4453 0.074 Uiso 1 1 calc R . . H21C H 0.1132 -0.1010 0.5381 0.074 Uiso 1 1 calc R . . N1 N 0.3846(3) 0.1962(3) 0.1582(4) 0.0369(12) Uani 1 1 d . . . N2 N 0.2305(3) -0.0843(4) 0.2852(5) 0.0529(9) Uani 1 1 d . . . N3 N 0.0604(3) -0.0302(4) 0.4137(5) 0.0496(7) Uani 1 1 d . . . O1 O 0.31220(17) 0.2605(2) 0.4899(3) 0.0231(8) Uani 1 1 d . . . O2 O 0.28684(18) 0.1790(2) 0.3630(3) 0.0289(9) Uani 1 1 d . . . O3 O 0.4075(3) 0.2572(3) 0.2137(4) 0.0681(17) Uani 1 1 d . . . O4 O 0.3483(3) 0.2027(3) 0.0672(4) 0.0568(14) Uani 1 1 d . . . O5 O 0.27962(18) -0.0909(2) 0.0234(3) 0.0264(8) Uani 1 1 d . . . O6 O 0.3332(2) -0.1776(2) 0.1561(3) 0.0302(9) Uani 1 1 d . . . O7 O 0.63704(17) 0.3011(2) 0.6947(3) 0.0238(8) Uani 1 1 d . . . O8 O 0.56653(17) 0.3240(2) 0.7407(3) 0.0260(8) Uani 1 1 d . . . O9 O 0.49892(19) 0.1580(3) 0.3641(3) 0.0348(10) Uani 1 1 d . . . O10 O 0.1872(3) 0.0350(3) 0.3036(4) 0.0529(9) Uani 1 1 d . . . O11 O 0.1311(2) 0.0700(3) 0.4226(4) 0.0496(7) Uani 1 1 d . . . C16 C 0.2346(9) -0.0123(9) 0.3314(13) 0.0529(9) Uani 0.50 1 d P A 1 H16 H 0.2776 0.0027 0.3898 0.080 Uiso 0.50 1 calc PR A 1 C16' C 0.2102(8) -0.0383(9) 0.3302(13) 0.0529(9) Uani 0.50 1 d P A 2 H16' H 0.2130 -0.0617 0.3864 0.080 Uiso 0.50 1 calc PR A 2 C17 C 0.2967(9) -0.1284(11) 0.3277(14) 0.0529(9) Uani 0.40 1 d P A 1 H17A H 0.3304 -0.0884 0.3334 0.079 Uiso 0.40 1 calc PR A 1 H17B H 0.2906 -0.1754 0.2839 0.079 Uiso 0.40 1 calc PR A 1 H17C H 0.3127 -0.1505 0.3939 0.079 Uiso 0.40 1 calc PR A 1 C17' C 0.2532(7) -0.1745(7) 0.3203(9) 0.0529(9) Uani 0.60 1 d P A 2 H17D H 0.2703 -0.1790 0.3910 0.079 Uiso 0.60 1 calc PR A 2 H17E H 0.2897 -0.1899 0.3117 0.079 Uiso 0.60 1 calc PR A 2 H17F H 0.2144 -0.2130 0.2810 0.079 Uiso 0.60 1 calc PR A 2 C18 C 0.1977(8) -0.0696(9) 0.1726(11) 0.0529(9) Uani 0.50 1 d P A 1 H18A H 0.1854 -0.0097 0.1566 0.079 Uiso 0.50 1 calc PR A 1 H18B H 0.1565 -0.1047 0.1336 0.079 Uiso 0.50 1 calc PR A 1 H18C H 0.2304 -0.0853 0.1563 0.079 Uiso 0.50 1 calc PR A 1 C18' C 0.1782(8) -0.1022(9) 0.1896(11) 0.0529(9) Uani 0.50 1 d P A 2 H18D H 0.1574 -0.0491 0.1533 0.079 Uiso 0.50 1 calc PR A 2 H18E H 0.1437 -0.1363 0.1898 0.079 Uiso 0.50 1 calc PR A 2 H18F H 0.1959 -0.1339 0.1567 0.079 Uiso 0.50 1 calc PR A 2 O1W O 0.2478(13) -0.341(2) 0.340(2) 0.103(10) Uani 0.25 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 Nd1 0.01195(14) 0.01707(15) 0.01492(14) 0.00037(11) 0.00534(11) 0.00110(11) C1 0.017(3) 0.024(3) 0.020(3) -0.004(2) 0.010(2) 0.000(2) C2 0.019(3) 0.033(3) 0.021(3) -0.008(2) 0.010(2) -0.008(2) C3 0.025(3) 0.023(3) 0.027(3) -0.006(2) 0.017(2) -0.005(2) C4 0.015(3) 0.021(3) 0.028(3) -0.005(2) 0.011(2) -0.004(2) C5 0.017(3) 0.018(2) 0.019(3) -0.001(2) 0.009(2) 0.000(2) C6 0.014(3) 0.028(3) 0.018(3) -0.005(2) 0.007(2) -0.002(2) C7 0.024(3) 0.037(3) 0.034(3) -0.023(3) 0.021(3) -0.018(3) C8 0.025(3) 0.024(3) 0.029(3) -0.007(2) 0.018(3) -0.006(2) C9 0.027(3) 0.028(3) 0.022(3) -0.005(2) 0.013(2) -0.002(2) C10 0.021(3) 0.020(3) 0.023(3) -0.006(2) 0.009(2) -0.004(2) C11 0.036(3) 0.026(3) 0.031(3) -0.005(3) 0.015(3) -0.006(3) C12 0.029(3) 0.038(3) 0.025(3) -0.007(3) 0.013(3) -0.008(3) C13 0.017(3) 0.026(3) 0.017(3) 0.002(2) 0.010(2) -0.001(2) C14 0.024(3) 0.021(3) 0.023(3) -0.005(2) 0.011(2) -0.004(2) C15 0.017(3) 0.018(2) 0.016(2) 0.002(2) 0.007(2) 0.003(2) C19 0.0447(16) 0.0421(15) 0.0589(18) 0.0065(13) 0.0272(14) -0.0105(12) C20 0.0447(16) 0.0421(15) 0.0589(18) 0.0065(13) 0.0272(14) -0.0105(12) C21 0.0447(16) 0.0421(15) 0.0589(18) 0.0065(13) 0.0272(14) -0.0105(12) N1 0.047(3) 0.023(3) 0.048(3) -0.006(2) 0.031(3) -0.007(2) N2 0.059(2) 0.0405(18) 0.0501(19) -0.0087(16) 0.0250(17) 0.0140(15) N3 0.0447(16) 0.0421(15) 0.0589(18) 0.0065(13) 0.0272(14) -0.0105(12) O1 0.0218(19) 0.0263(19) 0.026(2) -0.0006(16) 0.0165(17) 0.0011(16) O2 0.0149(18) 0.047(2) 0.0225(19) -0.0120(18) 0.0092(16) -0.0050(17) O3 0.117(5) 0.026(3) 0.069(4) -0.014(3) 0.057(4) -0.020(3) O4 0.061(3) 0.039(3) 0.050(3) 0.007(2) 0.019(3) -0.004(2) O5 0.024(2) 0.0207(19) 0.022(2) -0.0029(15) 0.0051(17) -0.0044(16) O6 0.038(2) 0.0175(19) 0.0216(19) -0.0010(16) 0.0083(18) -0.0059(17) O7 0.0131(17) 0.036(2) 0.0213(19) -0.0022(16) 0.0091(16) -0.0029(16) O8 0.0177(18) 0.037(2) 0.0200(18) -0.0075(17) 0.0082(16) -0.0001(17) O9 0.027(2) 0.046(3) 0.041(2) -0.027(2) 0.025(2) -0.0210(19) O10 0.059(2) 0.0405(18) 0.0501(19) -0.0087(16) 0.0250(17) 0.0140(15) O11 0.0447(16) 0.0421(15) 0.0589(18) 0.0065(13) 0.0272(14) -0.0105(12) C16 0.059(2) 0.0405(18) 0.0501(19) -0.0087(16) 0.0250(17) 0.0140(15) C16' 0.059(2) 0.0405(18) 0.0501(19) -0.0087(16) 0.0250(17) 0.0140(15) C17 0.059(2) 0.0405(18) 0.0501(19) -0.0087(16) 0.0250(17) 0.0140(15) C17' 0.059(2) 0.0405(18) 0.0501(19) -0.0087(16) 0.0250(17) 0.0140(15) C18 0.059(2) 0.0405(18) 0.0501(19) -0.0087(16) 0.0250(17) 0.0140(15) C18' 0.059(2) 0.0405(18) 0.0501(19) -0.0087(16) 0.0250(17) 0.0140(15) O1W 0.080(18) 0.16(3) 0.09(2) 0.041(19) 0.059(17) -0.019(18) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag Nd1 O1 2.406(3) 7_556 ? Nd1 O6 2.437(3) 4 ? Nd1 O10 2.456(4) . ? Nd1 O5 2.456(3) 6_556 ? Nd1 O11 2.461(4) . ? Nd1 O2 2.462(3) . ? Nd1 O8 2.475(3) 8_455 ? Nd1 O7 2.542(4) 8_455 ? Nd1 O1 2.788(3) . ? Nd1 C15 2.850(5) 8_455 ? Nd1 C13 2.980(5) . ? C1 C6 1.392(7) . ? C1 C2 1.394(7) . ? C1 C13 1.498(7) . ? C2 C3 1.386(7) . ? C3 C4 1.376(7) . ? C3 O9 1.390(6) . ? C4 C5 1.397(7) . ? C5 C6 1.393(7) . ? C5 C15 1.492(7) . ? C7 C12 1.378(8) . ? C7 C8 1.388(8) . ? C7 O9 1.399(6) . ? C8 C9 1.388(7) . ? C8 N1 1.462(7) . ? C9 C10 1.384(7) . ? C10 C11 1.391(8) . ? C10 C14 1.500(7) . ? C11 C12 1.379(8) . ? C13 O2 1.255(6) . ? C13 O1 1.268(6) . ? C14 O5 1.255(6) . ? C14 O6 1.255(6) . ? C15 O7 1.255(6) . ? C15 O8 1.271(6) . ? C15 Nd1 2.850(5) 8_556 ? C19 O11 1.229(7) . ? C19 N3 1.311(8) . ? C20 N3 1.467(8) . ? C21 N3 1.457(8) . ? N1 O3 1.217(6) . ? N1 O4 1.224(7) . ? N2 C16' 1.298(16) . ? N2 C16 1.334(15) . ? N2 C18' 1.362(15) . ? N2 C17 1.480(17) . ? N2 C17' 1.513(12) . ? N2 C18 1.548(16) . ? O1 Nd1 2.406(3) 7_556 ? O5 Nd1 2.456(3) 6 ? O6 Nd1 2.437(3) 4_545 ? O7 Nd1 2.542(4) 8_556 ? O8 Nd1 2.475(3) 8_556 ? O10 C16 1.203(15) . ? O10 C16' 1.245(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 O1 Nd1 O6 69.99(12) 7_556 4 ? O1 Nd1 O10 145.45(15) 7_556 . ? O6 Nd1 O10 143.13(15) 4 . ? O1 Nd1 O5 79.77(12) 7_556 6_556 ? O6 Nd1 O5 133.19(12) 4 6_556 ? O10 Nd1 O5 77.67(14) . 6_556 ? O1 Nd1 O11 75.16(14) 7_556 . ? O6 Nd1 O11 128.08(15) 4 . ? O10 Nd1 O11 73.53(17) . . ? O5 Nd1 O11 73.46(14) 6_556 . ? O1 Nd1 O2 123.48(12) 7_556 . ? O6 Nd1 O2 91.30(13) 4 . ? O10 Nd1 O2 75.61(15) . . ? O5 Nd1 O2 76.31(13) 6_556 . ? O11 Nd1 O2 140.46(15) . . ? O1 Nd1 O8 101.07(12) 7_556 8_455 ? O6 Nd1 O8 76.67(12) 4 8_455 ? O10 Nd1 O8 83.81(14) . 8_455 ? O5 Nd1 O8 145.65(12) 6_556 8_455 ? O11 Nd1 O8 73.66(14) . 8_455 ? O2 Nd1 O8 126.58(12) . 8_455 ? O1 Nd1 O7 136.31(12) 7_556 8_455 ? O6 Nd1 O7 70.28(12) 4 8_455 ? O10 Nd1 O7 73.02(14) . 8_455 ? O5 Nd1 O7 142.81(12) 6_556 8_455 ? O11 Nd1 O7 117.99(14) . 8_455 ? O2 Nd1 O7 74.64(11) . 8_455 ? O8 Nd1 O7 52.17(11) 8_455 8_455 ? O1 Nd1 O1 74.40(12) 7_556 . ? O6 Nd1 O1 70.66(12) 4 . ? O10 Nd1 O1 119.03(14) . . ? O5 Nd1 O1 67.23(11) 6_556 . ? O11 Nd1 O1 133.52(14) . . ? O2 Nd1 O1 49.17(11) . . ? O8 Nd1 O1 146.59(11) 8_455 . ? O7 Nd1 O1 108.31(11) 8_455 . ? O1 Nd1 C15 118.34(13) 7_556 8_455 ? O6 Nd1 C15 68.25(13) 4 8_455 ? O10 Nd1 C15 80.35(15) . 8_455 ? O5 Nd1 C15 157.86(13) 6_556 8_455 ? O11 Nd1 C15 97.83(15) . 8_455 ? O2 Nd1 C15 100.74(13) . 8_455 ? O8 Nd1 C15 26.43(13) 8_455 8_455 ? O7 Nd1 C15 26.12(12) 8_455 8_455 ? O1 Nd1 C15 127.48(12) . 8_455 ? O1 Nd1 C13 99.15(13) 7_556 . ? O6 Nd1 C13 82.95(14) 4 . ? O10 Nd1 C13 95.84(16) . . ? O5 Nd1 C13 67.25(13) 6_556 . ? O11 Nd1 C13 140.66(15) . . ? O2 Nd1 C13 24.35(13) . . ? O8 Nd1 C13 144.16(13) 8_455 . ? O7 Nd1 C13 93.31(12) 8_455 . ? O1 Nd1 C13 25.12(12) . . ? C15 Nd1 C13 118.01(14) 8_455 . ? C6 C1 C2 119.8(5) . . ? C6 C1 C13 122.5(4) . . ? C2 C1 C13 117.7(4) . . ? C3 C2 C1 119.7(5) . . ? C4 C3 C2 121.0(5) . . ? C4 C3 O9 117.0(4) . . ? C2 C3 O9 122.0(5) . . ? C3 C4 C5 119.6(5) . . ? C6 C5 C4 120.0(5) . . ? C6 C5 C15 120.9(4) . . ? C4 C5 C15 119.0(4) . . ? C1 C6 C5 119.8(5) . . ? C12 C7 C8 119.8(5) . . ? C12 C7 O9 117.3(5) . . ? C8 C7 O9 122.9(5) . . ? C7 C8 C9 119.8(5) . . ? C7 C8 N1 122.9(5) . . ? C9 C8 N1 117.3(5) . . ? C10 C9 C8 120.7(5) . . ? C9 C10 C11 118.7(5) . . ? C9 C10 C14 120.6(5) . . ? C11 C10 C14 120.7(5) . . ? C12 C11 C10 120.9(5) . . ? C7 C12 C11 120.1(5) . . ? O2 C13 O1 121.8(5) . . ? O2 C13 C1 117.9(4) . . ? O1 C13 C1 120.3(4) . . ? O2 C13 Nd1 54.0(2) . . ? O1 C13 Nd1 69.0(3) . . ? C1 C13 Nd1 165.9(3) . . ? O5 C14 O6 126.8(5) . . ? O5 C14 C10 117.0(5) . . ? O6 C14 C10 116.2(5) . . ? O7 C15 O8 121.7(5) . . ? O7 C15 C5 119.4(4) . . ? O8 C15 C5 118.8(4) . . ? O7 C15 Nd1 63.1(3) . 8_556 ? O8 C15 Nd1 60.1(2) . 8_556 ? C5 C15 Nd1 166.3(3) . 8_556 ? O11 C19 N3 124.3(7) . . ? O3 N1 O4 122.9(6) . . ? O3 N1 C8 119.1(5) . . ? O4 N1 C8 118.1(5) . . ? C16' N2 C16 30.8(9) . . ? C16' N2 C18' 111.7(10) . . ? C16 N2 C18' 123.3(10) . . ? C16' N2 C17 129.0(11) . . ? C16 N2 C17 114.5(11) . . ? C18' N2 C17 118.5(10) . . ? C16' N2 C17' 118.6(10) . . ? C16 N2 C17' 133.7(10) . . ? C18' N2 C17' 97.8(9) . . ? C17 N2 C17' 47.6(8) . . ? C16' N2 C18 118.8(10) . . ? C16 N2 C18 111.4(10) . . ? C18' N2 C18 32.5(8) . . ? C17 N2 C18 108.4(10) . . ? C17' N2 C18 114.8(8) . . ? C19 N3 C21 121.0(6) . . ? C19 N3 C20 121.7(6) . . ? C21 N3 C20 117.2(5) . . ? C13 O1 Nd1 164.8(3) . 7_556 ? C13 O1 Nd1 85.9(3) . . ? Nd1 O1 Nd1 105.60(12) 7_556 . ? C13 O2 Nd1 101.6(3) . . ? C14 O5 Nd1 135.3(3) . 6 ? C14 O6 Nd1 141.4(3) . 4_545 ? C15 O7 Nd1 90.8(3) . 8_556 ? C15 O8 Nd1 93.5(3) . 8_556 ? C3 O9 C7 114.7(4) . . ? C16 O10 C16' 33.2(9) . . ? C16 O10 Nd1 127.0(8) . . ? C16' O10 Nd1 139.2(8) . . ? C19 O11 Nd1 139.6(5) . . ? O10 C16 N2 124.0(14) . . ? O10 C16' N2 123.5(15) . . ? _diffrn_measured_fraction_theta_max 0.993 _diffrn_reflns_theta_full 26.08 _diffrn_measured_fraction_theta_full 0.993 _refine_diff_density_max 1.719 _refine_diff_density_min -2.077 _refine_diff_density_rms 0.134 data_5 _database_code_depnum_ccdc_archive 'CCDC 857006' #TrackingRef '- 1-12 and 7.CIF' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point 'not measured' _chemical_formula_moiety 'C21 H20.50 N3 O11.25 Sm' _chemical_formula_sum 'C21 H20.50 N3 O11.25 Sm' _chemical_formula_weight 645.25 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Sm Sm -0.1638 3.4418 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Monoclinic _symmetry_space_group_name_H-M C2/c loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y, -z+1/2' 'x+1/2, y+1/2, z' '-x+1/2, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y, z-1/2' '-x+1/2, -y+1/2, -z' 'x+1/2, -y+1/2, z-1/2' _cell_length_a 23.6108(10) _cell_length_b 15.7288(7) _cell_length_c 16.1612(13) _cell_angle_alpha 90.00 _cell_angle_beta 124.2910(10) _cell_angle_gamma 90.00 _cell_volume 4958.6(5) _cell_formula_units_Z 8 _cell_measurement_temperature 185(2) _cell_measurement_reflns_used 4945 _cell_measurement_theta_min 1.66 _cell_measurement_theta_max 26.11 _exptl_crystal_description rod _exptl_crystal_colour 'light yellow' _exptl_crystal_size_max 0.22 _exptl_crystal_size_mid 0.16 _exptl_crystal_size_min 0.13 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.729 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 2556 _exptl_absorpt_coefficient_mu 2.433 _exptl_absorpt_correction_type empirical _exptl_absorpt_correction_T_min 0.6166 _exptl_absorpt_correction_T_max 0.7427 _exptl_absorpt_process_details SADABS _exptl_special_details ; ? ; _diffrn_ambient_temperature 185(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'CCD area detector' _diffrn_measurement_method 'phi and omega scans' _diffrn_detector_area_resol_mean 9.00cm _diffrn_standards_number none _diffrn_standards_interval_count none _diffrn_standards_interval_time none _diffrn_standards_decay_% none _diffrn_reflns_number 13648 _diffrn_reflns_av_R_equivalents 0.0374 _diffrn_reflns_av_sigmaI/netI 0.0454 _diffrn_reflns_limit_h_min -29 _diffrn_reflns_limit_h_max 18 _diffrn_reflns_limit_k_min -19 _diffrn_reflns_limit_k_max 19 _diffrn_reflns_limit_l_min -12 _diffrn_reflns_limit_l_max 20 _diffrn_reflns_theta_min 1.66 _diffrn_reflns_theta_max 26.11 _reflns_number_total 4945 _reflns_number_gt 4140 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SMART' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics SHELXP-97 _computing_publication_material SHELXTL _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0353P)^2^+33.5386P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 4945 _refine_ls_number_parameters 298 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0467 _refine_ls_R_factor_gt 0.0382 _refine_ls_wR_factor_ref 0.0911 _refine_ls_wR_factor_gt 0.0869 _refine_ls_goodness_of_fit_ref 1.050 _refine_ls_restrained_S_all 1.050 _refine_ls_shift/su_max 0.001 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group Sm1 Sm 0.310456(11) 0.671860(14) 0.621692(17) 0.01526(9) Uani 1 1 d . . . C1 C 0.0983(2) 0.7234(3) 0.5303(4) 0.0201(10) Uani 1 1 d . . . C2 C 0.0844(2) 0.6884(3) 0.5964(4) 0.0238(11) Uani 1 1 d . . . H2A H 0.1201 0.6626 0.6569 0.029 Uiso 1 1 calc R . . C3 C 0.0187(2) 0.6912(3) 0.5735(4) 0.0221(11) Uani 1 1 d . . . C4 C -0.0343(2) 0.7277(3) 0.4857(4) 0.0203(10) Uani 1 1 d . . . H4A H -0.0792 0.7297 0.4713 0.024 Uiso 1 1 calc R . . C5 C -0.0210(2) 0.7616(3) 0.4182(3) 0.0194(10) Uani 1 1 d . . . C6 C 0.0449(2) 0.7581(3) 0.4395(4) 0.0211(10) Uani 1 1 d . . . H6A H 0.0535 0.7792 0.3926 0.025 Uiso 1 1 calc R . . C7 C 0.0456(2) 0.5952(3) 0.7018(4) 0.0254(11) Uani 1 1 d . . . C8 C 0.0999(3) 0.6102(3) 0.8001(4) 0.0237(11) Uani 1 1 d . . . C9 C 0.1409(3) 0.5446(3) 0.8604(4) 0.0253(11) Uani 1 1 d . . . H9A H 0.1775 0.5558 0.9278 0.030 Uiso 1 1 calc R . . C10 C 0.1293(2) 0.4627(3) 0.8239(4) 0.0236(11) Uani 1 1 d . . . C11 C 0.0739(3) 0.4468(3) 0.7267(4) 0.0292(12) Uani 1 1 d . . . H11A H 0.0646 0.3904 0.7015 0.035 Uiso 1 1 calc R . . C12 C 0.0320(3) 0.5127(4) 0.6662(4) 0.0306(12) Uani 1 1 d . . . H12A H -0.0061 0.5011 0.6000 0.037 Uiso 1 1 calc R . . C13 C 0.1705(2) 0.7223(3) 0.5590(4) 0.0208(10) Uani 1 1 d . . . C14 C 0.1771(2) 0.3909(3) 0.8877(4) 0.0220(11) Uani 1 1 d . . . C15 C -0.0792(2) 0.7977(3) 0.3210(4) 0.0201(10) Uani 1 1 d . . . C19 C 0.4258(3) 0.5434(4) 0.6116(5) 0.0497(7) Uani 1 1 d . A . H19A H 0.4634 0.5785 0.6579 0.060 Uiso 1 1 calc R . . C20 C 0.3836(3) 0.4124(4) 0.5186(5) 0.0497(7) Uani 1 1 d . . . H20A H 0.3394 0.4393 0.4946 0.075 Uiso 1 1 calc R . . H20B H 0.3879 0.3596 0.5540 0.075 Uiso 1 1 calc R . . H20C H 0.3862 0.3996 0.4615 0.075 Uiso 1 1 calc R . . C21 C 0.5093(3) 0.4434(4) 0.6296(5) 0.0497(7) Uani 1 1 d . . . H21A H 0.5409 0.4888 0.6720 0.075 Uiso 1 1 calc R . . H21B H 0.5153 0.4309 0.5756 0.075 Uiso 1 1 calc R . . H21C H 0.5191 0.3922 0.6702 0.075 Uiso 1 1 calc R . . N1 N 0.1161(3) 0.6959(3) 0.8433(4) 0.0366(12) Uani 1 1 d . . . N2 N 0.2695(3) 0.4176(3) 0.7162(4) 0.0489(8) Uani 1 1 d . . . N3 N 0.4393(3) 0.4703(3) 0.5871(4) 0.0497(7) Uani 1 1 d . . . O1 O 0.18694(16) 0.7615(2) 0.5078(3) 0.0219(7) Uani 1 1 d . . . O2 O 0.21358(17) 0.6816(2) 0.6364(3) 0.0281(8) Uani 1 1 d . . . O3 O 0.0937(3) 0.7572(3) 0.7876(4) 0.0675(16) Uani 1 1 d . . . O4 O 0.1524(2) 0.7022(3) 0.9344(4) 0.0562(13) Uani 1 1 d . . . O5 O 0.22096(16) 0.4077(2) 0.9789(2) 0.0245(8) Uani 1 1 d . . . O6 O 0.16829(19) 0.3221(2) 0.8442(3) 0.0295(9) Uani 1 1 d . . . O7 O -0.13785(16) 0.8005(2) 0.3046(3) 0.0238(8) Uani 1 1 d . . . O8 O -0.06765(16) 0.8227(2) 0.2575(2) 0.0250(8) Uani 1 1 d . . . O9 O 0.00225(18) 0.6584(2) 0.6369(3) 0.0334(9) Uani 1 1 d . . . O10 O 0.3121(2) 0.5379(3) 0.6972(3) 0.0489(8) Uani 1 1 d . . . O11 O 0.3675(2) 0.5695(3) 0.5785(4) 0.0497(7) Uani 1 1 d . . . C16 C 0.2868(7) 0.4663(9) 0.6697(12) 0.0489(8) Uani 0.50 1 d P A 1 H16A H 0.2794 0.4452 0.6093 0.059 Uiso 0.50 1 calc PR A 1 C16' C 0.2642(8) 0.4918(9) 0.6702(12) 0.0489(8) Uani 0.50 1 d P A 2 H16B H 0.2205 0.5083 0.6139 0.059 Uiso 0.50 1 calc PR A 2 C17 C 0.3231(6) 0.4048(7) 0.8180(8) 0.0489(8) Uani 0.60 1 d P A 1 H17A H 0.3381 0.4598 0.8524 0.073 Uiso 0.60 1 calc PR A 1 H17B H 0.3617 0.3767 0.8223 0.073 Uiso 0.60 1 calc PR A 1 H17C H 0.3066 0.3690 0.8500 0.073 Uiso 0.60 1 calc PR A 1 C17' C 0.2936(9) 0.4337(11) 0.8217(13) 0.0489(8) Uani 0.40 1 d P A 2 H17D H 0.3001 0.4949 0.8351 0.073 Uiso 0.40 1 calc PR A 2 H17E H 0.3372 0.4042 0.8666 0.073 Uiso 0.40 1 calc PR A 2 H17F H 0.2594 0.4126 0.8330 0.073 Uiso 0.40 1 calc PR A 2 C18 C 0.1972(12) 0.3794(15) 0.6670(19) 0.0489(8) Uani 0.30 1 d P A 1 H18A H 0.1662 0.4226 0.6639 0.073 Uiso 0.30 1 calc PR A 1 H18B H 0.1992 0.3309 0.7066 0.073 Uiso 0.30 1 calc PR A 1 H18C H 0.1802 0.3604 0.5990 0.073 Uiso 0.30 1 calc PR A 1 C18' C 0.2541(10) 0.3216(10) 0.6774(13) 0.0489(8) Uani 0.40 1 d P A 2 H18D H 0.2956 0.2961 0.6884 0.073 Uiso 0.40 1 calc PR A 2 H18E H 0.2174 0.3206 0.6058 0.073 Uiso 0.40 1 calc PR A 2 H18F H 0.2396 0.2892 0.7144 0.073 Uiso 0.40 1 calc PR A 2 C18" C 0.2215(13) 0.3485(15) 0.6836(19) 0.0489(8) Uani 0.30 1 d P A 3 H18G H 0.1817 0.3669 0.6831 0.073 Uiso 0.30 1 calc PR A 3 H18H H 0.2436 0.3004 0.7295 0.073 Uiso 0.30 1 calc PR A 3 H18I H 0.2066 0.3312 0.6159 0.073 Uiso 0.30 1 calc PR A 3 O1W O 0.2529(10) 0.1594(16) 0.6599(17) 0.076(7) Uani 0.25 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 Sm1 0.01138(13) 0.01608(13) 0.01293(13) -0.00061(10) 0.00359(10) -0.00129(9) C1 0.015(2) 0.025(3) 0.018(2) 0.002(2) 0.008(2) 0.0024(19) C2 0.017(2) 0.029(3) 0.021(3) 0.006(2) 0.008(2) 0.008(2) C3 0.021(2) 0.022(3) 0.024(3) 0.009(2) 0.013(2) 0.006(2) C4 0.017(2) 0.019(2) 0.023(3) 0.003(2) 0.010(2) 0.0023(19) C5 0.019(2) 0.021(2) 0.013(2) 0.0030(19) 0.0052(19) 0.0000(19) C6 0.018(2) 0.025(3) 0.017(2) 0.001(2) 0.008(2) 0.000(2) C7 0.020(2) 0.035(3) 0.024(3) 0.016(2) 0.014(2) 0.009(2) C8 0.028(3) 0.019(2) 0.030(3) 0.005(2) 0.019(2) 0.004(2) C9 0.023(3) 0.024(3) 0.023(3) 0.004(2) 0.010(2) 0.003(2) C10 0.023(3) 0.024(3) 0.021(3) 0.004(2) 0.011(2) 0.005(2) C11 0.031(3) 0.023(3) 0.023(3) 0.003(2) 0.009(2) 0.002(2) C12 0.023(3) 0.036(3) 0.021(3) 0.003(2) 0.005(2) 0.002(2) C13 0.017(2) 0.026(3) 0.017(3) -0.001(2) 0.008(2) 0.001(2) C14 0.020(2) 0.020(2) 0.022(3) 0.007(2) 0.010(2) 0.006(2) C15 0.014(2) 0.021(2) 0.017(2) -0.004(2) 0.0033(19) 0.0003(19) C19 0.0462(15) 0.0424(15) 0.0560(17) -0.0055(13) 0.0261(13) 0.0110(12) C20 0.0462(15) 0.0424(15) 0.0560(17) -0.0055(13) 0.0261(13) 0.0110(12) C21 0.0462(15) 0.0424(15) 0.0560(17) -0.0055(13) 0.0261(13) 0.0110(12) N1 0.044(3) 0.026(2) 0.045(3) 0.006(2) 0.028(3) 0.007(2) N2 0.053(2) 0.0382(17) 0.0454(17) 0.0070(14) 0.0216(15) -0.0121(14) N3 0.0462(15) 0.0424(15) 0.0560(17) -0.0055(13) 0.0261(13) 0.0110(12) O1 0.0189(17) 0.0250(18) 0.0239(19) -0.0001(15) 0.0133(15) -0.0010(14) O2 0.0135(16) 0.046(2) 0.0219(19) 0.0087(17) 0.0081(15) 0.0040(15) O3 0.112(5) 0.028(2) 0.062(4) 0.019(2) 0.049(3) 0.019(3) O4 0.058(3) 0.035(2) 0.045(3) -0.004(2) 0.011(2) 0.003(2) O5 0.0207(17) 0.0215(18) 0.0171(18) 0.0007(14) 0.0020(15) 0.0013(14) O6 0.036(2) 0.0190(19) 0.0209(19) 0.0007(15) 0.0085(16) 0.0060(16) O7 0.0153(17) 0.0328(19) 0.0191(19) 0.0017(15) 0.0071(14) 0.0035(14) O8 0.0148(16) 0.038(2) 0.0161(18) 0.0074(16) 0.0051(14) 0.0012(15) O9 0.0272(19) 0.044(2) 0.036(2) 0.0251(18) 0.0216(18) 0.0184(17) O10 0.053(2) 0.0382(17) 0.0454(17) 0.0070(14) 0.0216(15) -0.0121(14) O11 0.0462(15) 0.0424(15) 0.0560(17) -0.0055(13) 0.0261(13) 0.0110(12) C16 0.053(2) 0.0382(17) 0.0454(17) 0.0070(14) 0.0216(15) -0.0121(14) C16' 0.053(2) 0.0382(17) 0.0454(17) 0.0070(14) 0.0216(15) -0.0121(14) C17 0.053(2) 0.0382(17) 0.0454(17) 0.0070(14) 0.0216(15) -0.0121(14) C17' 0.053(2) 0.0382(17) 0.0454(17) 0.0070(14) 0.0216(15) -0.0121(14) C18 0.053(2) 0.0382(17) 0.0454(17) 0.0070(14) 0.0216(15) -0.0121(14) C18' 0.053(2) 0.0382(17) 0.0454(17) 0.0070(14) 0.0216(15) -0.0121(14) C18" 0.053(2) 0.0382(17) 0.0454(17) 0.0070(14) 0.0216(15) -0.0121(14) O1W 0.046(12) 0.12(2) 0.067(15) -0.036(14) 0.032(11) 0.005(12) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag Sm1 O1 2.372(3) 7_566 ? Sm1 O6 2.414(3) 4_556 ? Sm1 O5 2.421(3) 6_565 ? Sm1 O10 2.424(4) . ? Sm1 O2 2.434(3) . ? Sm1 O11 2.440(4) . ? Sm1 O8 2.447(3) 8_566 ? Sm1 O7 2.520(3) 8_566 ? Sm1 O1 2.798(3) . ? Sm1 C15 2.816(5) 8_566 ? Sm1 C13 2.967(5) . ? C1 C2 1.396(7) . ? C1 C6 1.398(6) . ? C1 C13 1.494(6) . ? C2 C3 1.378(7) . ? C3 C4 1.381(7) . ? C3 O9 1.384(6) . ? C4 C5 1.400(7) . ? C5 C6 1.392(7) . ? C5 C15 1.499(6) . ? C7 C12 1.382(8) . ? C7 O9 1.388(6) . ? C7 C8 1.389(7) . ? C8 C9 1.374(7) . ? C8 N1 1.465(7) . ? C9 C10 1.379(7) . ? C10 C11 1.388(7) . ? C10 C14 1.516(6) . ? C11 C12 1.385(7) . ? C13 O1 1.255(6) . ? C13 O2 1.256(6) . ? C14 O6 1.242(6) . ? C14 O5 1.262(6) . ? C15 O7 1.255(6) . ? C15 O8 1.264(6) . ? C15 Sm1 2.816(5) 8_465 ? C19 O11 1.232(7) . ? C19 N3 1.313(8) . ? C20 N3 1.464(8) . ? C21 N3 1.451(8) . ? N1 O3 1.218(6) . ? N1 O4 1.221(7) . ? N2 C16 1.289(15) . ? N2 C16' 1.351(14) . ? N2 C17 1.416(12) . ? N2 C18" 1.44(2) . ? N2 C17' 1.483(18) . ? N2 C18 1.54(2) . ? N2 C18' 1.596(17) . ? O1 Sm1 2.372(3) 7_566 ? O5 Sm1 2.421(3) 6_566 ? O6 Sm1 2.414(3) 4_546 ? O7 Sm1 2.520(3) 8_465 ? O8 Sm1 2.447(3) 8_465 ? O10 C16' 1.200(14) . ? O10 C16 1.235(14) . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag O1 Sm1 O6 70.33(12) 7_566 4_556 ? O1 Sm1 O5 80.19(12) 7_566 6_565 ? O6 Sm1 O5 132.91(12) 4_556 6_565 ? O1 Sm1 O10 145.78(14) 7_566 . ? O6 Sm1 O10 142.54(14) 4_556 . ? O5 Sm1 O10 77.81(13) 6_565 . ? O1 Sm1 O2 123.45(11) 7_566 . ? O6 Sm1 O2 90.12(13) 4_556 . ? O5 Sm1 O2 76.24(12) 6_565 . ? O10 Sm1 O2 75.84(14) . . ? O1 Sm1 O11 75.30(14) 7_566 . ? O6 Sm1 O11 129.32(15) 4_556 . ? O5 Sm1 O11 73.30(14) 6_565 . ? O10 Sm1 O11 73.46(16) . . ? O2 Sm1 O11 140.38(14) . . ? O1 Sm1 O8 100.02(12) 7_566 8_566 ? O6 Sm1 O8 76.89(12) 4_556 8_566 ? O5 Sm1 O8 145.75(11) 6_565 8_566 ? O10 Sm1 O8 84.33(13) . 8_566 ? O2 Sm1 O8 127.25(12) . 8_566 ? O11 Sm1 O8 73.69(13) . 8_566 ? O1 Sm1 O7 136.25(11) 7_566 8_566 ? O6 Sm1 O7 70.27(12) 4_556 8_566 ? O5 Sm1 O7 142.48(12) 6_565 8_566 ? O10 Sm1 O7 72.53(14) . 8_566 ? O2 Sm1 O7 74.65(11) . 8_566 ? O11 Sm1 O7 117.94(13) . 8_566 ? O8 Sm1 O7 52.74(11) 8_566 8_566 ? O1 Sm1 O1 74.48(11) 7_566 . ? O6 Sm1 O1 70.28(11) 4_556 . ? O5 Sm1 O1 66.85(11) 6_565 . ? O10 Sm1 O1 118.99(13) . . ? O2 Sm1 O1 49.02(11) . . ? O11 Sm1 O1 133.09(13) . . ? O8 Sm1 O1 146.67(11) 8_566 . ? O7 Sm1 O1 108.73(10) 8_566 . ? O1 Sm1 C15 117.82(13) 7_566 8_566 ? O6 Sm1 C15 68.48(13) 4_556 8_566 ? O5 Sm1 C15 157.84(13) 6_565 8_566 ? O10 Sm1 C15 80.21(14) . 8_566 ? O2 Sm1 C15 101.08(13) . 8_566 ? O11 Sm1 C15 97.77(15) . 8_566 ? O8 Sm1 C15 26.63(13) 8_566 8_566 ? O7 Sm1 C15 26.46(12) 8_566 8_566 ? O1 Sm1 C15 128.02(12) . 8_566 ? O1 Sm1 C13 99.08(12) 7_566 . ? O6 Sm1 C13 82.19(13) 4_556 . ? O5 Sm1 C13 66.85(13) 6_565 . ? O10 Sm1 C13 95.97(15) . . ? O2 Sm1 C13 24.43(12) . . ? O11 Sm1 C13 140.11(14) . . ? O8 Sm1 C13 144.85(12) 8_566 . ? O7 Sm1 C13 93.70(12) 8_566 . ? O1 Sm1 C13 24.93(12) . . ? C15 Sm1 C13 118.64(14) 8_566 . ? C2 C1 C6 119.7(4) . . ? C2 C1 C13 118.5(4) . . ? C6 C1 C13 121.9(4) . . ? C3 C2 C1 119.8(4) . . ? C2 C3 C4 121.4(5) . . ? C2 C3 O9 122.2(4) . . ? C4 C3 O9 116.5(4) . . ? C3 C4 C5 119.2(4) . . ? C6 C5 C4 120.1(4) . . ? C6 C5 C15 120.8(4) . . ? C4 C5 C15 119.0(4) . . ? C5 C6 C1 119.8(5) . . ? C12 C7 O9 117.3(5) . . ? C12 C7 C8 118.9(5) . . ? O9 C7 C8 123.7(5) . . ? C9 C8 C7 120.8(5) . . ? C9 C8 N1 117.5(5) . . ? C7 C8 N1 121.7(5) . . ? C8 C9 C10 120.5(5) . . ? C9 C10 C11 119.0(5) . . ? C9 C10 C14 120.9(4) . . ? C11 C10 C14 120.1(5) . . ? C12 C11 C10 120.5(5) . . ? C7 C12 C11 120.2(5) . . ? O1 C13 O2 122.0(4) . . ? O1 C13 C1 120.8(4) . . ? O2 C13 C1 117.2(4) . . ? O1 C13 Sm1 70.0(3) . . ? O2 C13 Sm1 53.3(2) . . ? C1 C13 Sm1 165.0(3) . . ? O6 C14 O5 127.4(4) . . ? O6 C14 C10 116.1(4) . . ? O5 C14 C10 116.4(4) . . ? O7 C15 O8 122.4(4) . . ? O7 C15 C5 119.1(5) . . ? O8 C15 C5 118.6(4) . . ? O7 C15 Sm1 63.5(2) . 8_465 ? O8 C15 Sm1 60.2(2) . 8_465 ? C5 C15 Sm1 166.9(3) . 8_465 ? O11 C19 N3 124.3(7) . . ? O3 N1 O4 122.9(5) . . ? O3 N1 C8 119.2(5) . . ? O4 N1 C8 117.8(5) . . ? C16 N2 C16' 29.3(8) . . ? C16 N2 C17 113.1(9) . . ? C16' N2 C17 120.5(9) . . ? C16 N2 C18" 132.6(13) . . ? C16' N2 C18" 129.9(13) . . ? C17 N2 C18" 108.8(11) . . ? C16 N2 C17' 121.7(10) . . ? C16' N2 C17' 110.0(10) . . ? C17 N2 C17' 34.5(8) . . ? C18" N2 C17' 105.3(13) . . ? C16 N2 C18 123.5(12) . . ? C16' N2 C18 108.7(12) . . ? C17 N2 C18 123.3(11) . . ? C18" N2 C18 26.1(12) . . ? C17' N2 C18 104.9(12) . . ? C16 N2 C18' 114.2(11) . . ? C16' N2 C18' 132.1(10) . . ? C17 N2 C18' 100.3(9) . . ? C18" N2 C18' 35.2(11) . . ? C17' N2 C18' 117.9(10) . . ? C18 N2 C18' 59.1(11) . . ? C19 N3 C21 121.2(6) . . ? C19 N3 C20 120.3(6) . . ? C21 N3 C20 118.4(5) . . ? C13 O1 Sm1 165.8(3) . 7_566 ? C13 O1 Sm1 85.0(3) . . ? Sm1 O1 Sm1 105.52(11) 7_566 . ? C13 O2 Sm1 102.3(3) . . ? C14 O5 Sm1 134.9(3) . 6_566 ? C14 O6 Sm1 140.9(3) . 4_546 ? C15 O7 Sm1 90.1(3) . 8_465 ? C15 O8 Sm1 93.2(3) . 8_465 ? C3 O9 C7 115.5(4) . . ? C16' O10 C16 31.9(9) . . ? C16' O10 Sm1 126.7(8) . . ? C16 O10 Sm1 138.2(8) . . ? C19 O11 Sm1 139.2(4) . . ? O10 C16 N2 125.5(14) . . ? O10 C16' N2 123.1(13) . . ? _diffrn_measured_fraction_theta_max 1.000 _diffrn_reflns_theta_full 26.11 _diffrn_measured_fraction_theta_full 1.000 _refine_diff_density_max 1.737 _refine_diff_density_min -2.085 _refine_diff_density_rms 0.134 data_6 _database_code_depnum_ccdc_archive 'CCDC 857007' #TrackingRef '- 1-12 and 7.CIF' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point 'not measured' _chemical_formula_moiety 'C21 H20.50 Eu N3 O11.25' _chemical_formula_sum 'C21 H20.50 Eu N3 O11.25' _chemical_formula_weight 646.86 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Eu Eu -0.1578 3.6682 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Monoclinic _symmetry_space_group_name_H-M C2/c loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y, -z+1/2' 'x+1/2, y+1/2, z' '-x+1/2, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y, z-1/2' '-x+1/2, -y+1/2, -z' 'x+1/2, -y+1/2, z-1/2' _cell_length_a 23.5849(11) _cell_length_b 15.7031(7) _cell_length_c 16.1371(7) _cell_angle_alpha 90.00 _cell_angle_beta 124.2740(10) _cell_angle_gamma 90.00 _cell_volume 4938.7(4) _cell_formula_units_Z 8 _cell_measurement_temperature 185(2) _cell_measurement_reflns_used 4885 _cell_measurement_theta_min 1.82 _cell_measurement_theta_max 26.05 _exptl_crystal_description rod _exptl_crystal_colour 'light yellow' _exptl_crystal_size_max 0.22 _exptl_crystal_size_mid 0.14 _exptl_crystal_size_min 0.11 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.740 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 2564 _exptl_absorpt_coefficient_mu 2.605 _exptl_absorpt_correction_type empirical _exptl_absorpt_correction_T_min 0.5980 _exptl_absorpt_correction_T_max 0.7626 _exptl_absorpt_process_details SADABS _exptl_special_details ; ? ; _diffrn_ambient_temperature 185(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'CCD area detector' _diffrn_measurement_method 'phi and omega scans' _diffrn_detector_area_resol_mean 9.00cm _diffrn_standards_number none _diffrn_standards_interval_count none _diffrn_standards_interval_time none _diffrn_standards_decay_% none _diffrn_reflns_number 13509 _diffrn_reflns_av_R_equivalents 0.0303 _diffrn_reflns_av_sigmaI/netI 0.0351 _diffrn_reflns_limit_h_min -29 _diffrn_reflns_limit_h_max 28 _diffrn_reflns_limit_k_min -19 _diffrn_reflns_limit_k_max 19 _diffrn_reflns_limit_l_min -15 _diffrn_reflns_limit_l_max 19 _diffrn_reflns_theta_min 1.82 _diffrn_reflns_theta_max 26.05 _reflns_number_total 4885 _reflns_number_gt 4239 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SMART' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics SHELXP-97 _computing_publication_material SHELXTL _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0417P)^2^+44.3878P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 4885 _refine_ls_number_parameters 289 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0438 _refine_ls_R_factor_gt 0.0375 _refine_ls_wR_factor_ref 0.0946 _refine_ls_wR_factor_gt 0.0908 _refine_ls_goodness_of_fit_ref 1.052 _refine_ls_restrained_S_all 1.052 _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 Eu1 Eu 0.189612(11) 0.672018(14) 0.378095(16) 0.01500(9) Uani 1 1 d . . . C1 C 0.3699(2) 0.5381(3) 0.6751(3) 0.0214(10) Uani 1 1 d . . . C2 C 0.3582(3) 0.4556(3) 0.6386(4) 0.0240(11) Uani 1 1 d . . . H2A H 0.3213 0.4444 0.5714 0.029 Uiso 1 1 calc R . . C3 C 0.3998(3) 0.3892(3) 0.6992(4) 0.0243(11) Uani 1 1 d . . . C4 C 0.4540(3) 0.4052(3) 0.7981(4) 0.0254(11) Uani 1 1 d . . . C5 C 0.4671(3) 0.4876(4) 0.8332(4) 0.0300(12) Uani 1 1 d . . . H5A H 0.5051 0.4991 0.8996 0.036 Uiso 1 1 calc R . . C6 C 0.4259(3) 0.5534(4) 0.7734(4) 0.0302(12) Uani 1 1 d . . . H6A H 0.4354 0.6098 0.7991 0.036 Uiso 1 1 calc R . . C7 C 0.4812(3) 0.3089(3) 0.9263(4) 0.0223(10) Uani 1 1 d . . . C8 C 0.5341(2) 0.2721(3) 1.0139(4) 0.0199(10) Uani 1 1 d . . . H8A H 0.5790 0.2698 1.0280 0.024 Uiso 1 1 calc R . . C9 C 0.5212(2) 0.2384(3) 1.0816(3) 0.0202(10) Uani 1 1 d . . . C10 C 0.4552(2) 0.2413(3) 1.0606(3) 0.0199(10) Uani 1 1 d . . . H10A H 0.4465 0.2197 1.1074 0.024 Uiso 1 1 calc R . . C11 C 0.4023(2) 0.2763(3) 0.9703(4) 0.0200(10) Uani 1 1 d . . . C12 C 0.4155(3) 0.3112(3) 0.9041(4) 0.0236(11) Uani 1 1 d . . . H12A H 0.3794 0.3367 0.8435 0.028 Uiso 1 1 calc R . . C13 C 0.3227(2) 0.6092(3) 0.6115(4) 0.0230(10) Uani 1 1 d . . . C14 C 0.5797(2) 0.2026(3) 1.1793(3) 0.0188(10) Uani 1 1 d . . . C15 C 0.3293(2) 0.2770(3) 0.9408(3) 0.0211(10) Uani 1 1 d . . . C16 C 0.2254(4) 0.4809(5) 0.3299(6) 0.0624(9) Uani 1 1 d . A . H16 H 0.2585 0.4803 0.4004 0.094 Uiso 1 1 calc R . . C17 C 0.2941(9) 0.3685(10) 0.3263(11) 0.0624(9) Uani 0.50 1 d P A 1 H17A H 0.3304 0.4054 0.3341 0.094 Uiso 0.50 1 calc PR A 1 H17B H 0.2860 0.3214 0.2811 0.094 Uiso 0.50 1 calc PR A 1 H17C H 0.3083 0.3458 0.3919 0.094 Uiso 0.50 1 calc PR A 1 C17' C 0.2509(9) 0.3251(9) 0.3201(12) 0.0624(9) Uani 0.50 1 d P A 2 H17D H 0.2108 0.2944 0.3085 0.094 Uiso 0.50 1 calc PR A 2 H17E H 0.2875 0.3245 0.3918 0.094 Uiso 0.50 1 calc PR A 2 H17F H 0.2671 0.2974 0.2827 0.094 Uiso 0.50 1 calc PR A 2 C18 C 0.1843(4) 0.4160(5) 0.1772(5) 0.0624(9) Uani 1 1 d . A . H18A H 0.1690 0.4740 0.1518 0.094 Uiso 1 1 calc R . . H18B H 0.1444 0.3808 0.1585 0.094 Uiso 1 1 calc R . . H18C H 0.2076 0.3918 0.1480 0.094 Uiso 1 1 calc R . . C19 C 0.0745(4) 0.5437(4) 0.3880(5) 0.0484(7) Uani 1 1 d . A . H19 H 0.0369 0.5788 0.3418 0.073 Uiso 1 1 calc R . . C20 C -0.0093(3) 0.4436(4) 0.3696(5) 0.0484(7) Uani 1 1 d . . . H20A H -0.0408 0.4894 0.3277 0.073 Uiso 1 1 calc R . . H20B H -0.0154 0.4305 0.4236 0.073 Uiso 1 1 calc R . . H20C H -0.0192 0.3926 0.3285 0.073 Uiso 1 1 calc R . . C21 C 0.1164(3) 0.4124(4) 0.4809(5) 0.0484(7) Uani 1 1 d . . . H21A H 0.1608 0.4393 0.5059 0.073 Uiso 1 1 calc R . . H21B H 0.1122 0.3600 0.4449 0.073 Uiso 1 1 calc R . . H21C H 0.1132 0.3989 0.5374 0.073 Uiso 1 1 calc R . . N1 N 0.3834(3) 0.3039(3) 0.6562(4) 0.0363(12) Uani 1 1 d . . . N2 N 0.2306(3) 0.4182(4) 0.2841(4) 0.0624(9) Uani 1 1 d . . . N3 N 0.0613(3) 0.4707(4) 0.4130(4) 0.0484(7) Uani 1 1 d . . . O1 O 0.3308(2) 0.6783(2) 0.6554(3) 0.0287(8) Uani 1 1 d . . . O2 O 0.27860(17) 0.5932(2) 0.5205(2) 0.0237(8) Uani 1 1 d . . . O3 O 0.3478(3) 0.2978(3) 0.5648(4) 0.0524(13) Uani 1 1 d . . . O4 O 0.4060(3) 0.2429(3) 0.7122(4) 0.0637(15) Uani 1 1 d . . . O5 O 0.28602(17) 0.3177(2) 0.8643(3) 0.0275(8) Uani 1 1 d . . . O6 O 0.31386(17) 0.2381(2) 0.9938(3) 0.0233(7) Uani 1 1 d . . . O7 O 0.56833(17) 0.1776(2) 1.2433(2) 0.0236(8) Uani 1 1 d . . . O8 O 0.63821(16) 0.1998(2) 1.1957(2) 0.0217(7) Uani 1 1 d . . . O9 O 0.49745(19) 0.3417(3) 0.8622(3) 0.0325(9) Uani 1 1 d . . . O10 O 0.1879(3) 0.5390(3) 0.3020(4) 0.0624(9) Uani 1 1 d . . . O11 O 0.1331(2) 0.5696(3) 0.4210(3) 0.0484(7) Uani 1 1 d . . . O1W O 0.2456(11) 0.1600(16) 0.3372(17) 0.071(7) Uani 0.25 1 d P . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 Eu1 0.01252(13) 0.01611(14) 0.01205(13) 0.00069(9) 0.00429(10) 0.00120(8) C1 0.022(2) 0.022(3) 0.017(2) 0.0035(19) 0.009(2) 0.0018(19) C2 0.023(2) 0.029(3) 0.021(2) 0.005(2) 0.012(2) 0.002(2) C3 0.028(3) 0.020(2) 0.031(3) 0.005(2) 0.020(2) 0.004(2) C4 0.024(3) 0.034(3) 0.025(3) 0.017(2) 0.018(2) 0.011(2) C5 0.024(3) 0.037(3) 0.019(2) 0.007(2) 0.006(2) 0.004(2) C6 0.031(3) 0.028(3) 0.021(3) 0.004(2) 0.008(2) 0.005(2) C7 0.024(2) 0.023(3) 0.024(3) 0.007(2) 0.015(2) 0.005(2) C8 0.017(2) 0.019(2) 0.023(2) 0.0032(19) 0.011(2) 0.0040(18) C9 0.021(2) 0.019(2) 0.016(2) -0.0002(18) 0.007(2) -0.0006(19) C10 0.023(2) 0.021(2) 0.016(2) 0.0017(18) 0.011(2) -0.0006(19) C11 0.022(2) 0.020(2) 0.018(2) 0.0013(18) 0.011(2) 0.0012(19) C12 0.019(2) 0.030(3) 0.019(2) 0.007(2) 0.009(2) 0.006(2) C13 0.023(2) 0.020(3) 0.019(2) 0.0037(19) 0.008(2) 0.001(2) C14 0.017(2) 0.018(2) 0.016(2) -0.0006(18) 0.0060(19) -0.0010(18) C15 0.019(2) 0.026(3) 0.016(2) -0.0041(19) 0.009(2) -0.0013(19) C16 0.070(2) 0.0529(18) 0.0467(17) -0.0080(14) 0.0221(16) 0.0272(15) C17 0.070(2) 0.0529(18) 0.0467(17) -0.0080(14) 0.0221(16) 0.0272(15) C17' 0.070(2) 0.0529(18) 0.0467(17) -0.0080(14) 0.0221(16) 0.0272(15) C18 0.070(2) 0.0529(18) 0.0467(17) -0.0080(14) 0.0221(16) 0.0272(15) C19 0.0467(15) 0.0425(15) 0.0529(16) 0.0057(12) 0.0263(13) -0.0103(12) C20 0.0467(15) 0.0425(15) 0.0529(16) 0.0057(12) 0.0263(13) -0.0103(12) C21 0.0467(15) 0.0425(15) 0.0529(16) 0.0057(12) 0.0263(13) -0.0103(12) N1 0.045(3) 0.024(2) 0.045(3) 0.008(2) 0.028(3) 0.007(2) N2 0.070(2) 0.0529(18) 0.0467(17) -0.0080(14) 0.0221(16) 0.0272(15) N3 0.0467(15) 0.0425(15) 0.0529(16) 0.0057(12) 0.0263(13) -0.0103(12) O1 0.036(2) 0.0193(19) 0.0171(17) 0.0016(14) 0.0064(16) 0.0054(15) O2 0.0207(17) 0.0214(18) 0.0166(17) 0.0013(13) 0.0030(14) 0.0031(14) O3 0.057(3) 0.034(2) 0.042(3) -0.006(2) 0.013(2) 0.005(2) O4 0.108(5) 0.027(2) 0.056(3) 0.015(2) 0.046(3) 0.018(3) O5 0.0161(17) 0.044(2) 0.0175(17) 0.0068(15) 0.0067(15) 0.0036(15) O6 0.0261(18) 0.0269(19) 0.0235(18) 0.0000(15) 0.0180(16) -0.0025(15) O7 0.0161(16) 0.034(2) 0.0162(17) 0.0063(14) 0.0067(14) -0.0006(14) O8 0.0161(16) 0.0316(19) 0.0157(16) 0.0033(14) 0.0079(14) 0.0025(14) O9 0.0274(19) 0.044(2) 0.036(2) 0.0272(18) 0.0240(18) 0.0201(17) O10 0.070(2) 0.0529(18) 0.0467(17) -0.0080(14) 0.0221(16) 0.0272(15) O11 0.0467(15) 0.0425(15) 0.0529(16) 0.0057(12) 0.0263(13) -0.0103(12) O1W 0.045(12) 0.110(19) 0.059(13) 0.044(13) 0.029(11) 0.002(12) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag Eu1 O6 2.356(3) 4_556 ? Eu1 O1 2.399(3) 7_566 ? Eu1 O2 2.406(3) . ? Eu1 O5 2.412(4) 6_565 ? Eu1 O10 2.412(5) . ? Eu1 O11 2.426(4) . ? Eu1 O7 2.432(3) 3_454 ? Eu1 O8 2.510(3) 3_454 ? Eu1 C14 2.807(5) 3_454 ? Eu1 O6 2.811(3) 6_565 ? Eu1 C15 2.959(5) 6_565 ? C1 C2 1.385(7) . ? C1 C6 1.399(7) . ? C1 C13 1.501(6) . ? C2 C3 1.387(7) . ? C3 C4 1.395(7) . ? C3 N1 1.457(7) . ? C4 C5 1.376(8) . ? C4 O9 1.386(6) . ? C5 C6 1.373(7) . ? C7 C8 1.379(7) . ? C7 C12 1.381(7) . ? C7 O9 1.389(6) . ? C8 C9 1.394(7) . ? C9 C10 1.394(7) . ? C9 C14 1.502(6) . ? C10 C11 1.390(6) . ? C11 C12 1.384(7) . ? C11 C15 1.506(7) . ? C13 O1 1.250(6) . ? C13 O2 1.257(6) . ? C14 O8 1.251(6) . ? C14 O7 1.266(6) . ? C14 Eu1 2.807(5) 3_546 ? C15 O5 1.247(6) . ? C15 O6 1.259(6) . ? C15 Eu1 2.959(5) 6_566 ? C16 O10 1.170(8) . ? C16 N2 1.279(8) . ? C17 N2 1.471(15) . ? C17' N2 1.546(15) . ? C18 N2 1.431(9) . ? C19 O11 1.236(8) . ? C19 N3 1.310(8) . ? C20 N3 1.461(8) . ? C21 N3 1.456(9) . ? N1 O4 1.214(6) . ? N1 O3 1.223(7) . ? O1 Eu1 2.399(3) 7_566 ? O5 Eu1 2.412(4) 6_566 ? O6 Eu1 2.356(3) 4_546 ? O6 Eu1 2.811(3) 6_566 ? O7 Eu1 2.432(3) 3_546 ? O8 Eu1 2.510(3) 3_546 ? 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 O6 Eu1 O1 70.39(12) 4_556 7_566 ? O6 Eu1 O2 80.26(12) 4_556 . ? O1 Eu1 O2 132.53(12) 7_566 . ? O6 Eu1 O5 123.52(12) 4_556 6_565 ? O1 Eu1 O5 89.64(13) 7_566 6_565 ? O2 Eu1 O5 76.25(12) . 6_565 ? O6 Eu1 O10 146.04(16) 4_556 . ? O1 Eu1 O10 142.20(15) 7_566 . ? O2 Eu1 O10 78.25(14) . . ? O5 Eu1 O10 75.97(17) 6_565 . ? O6 Eu1 O11 75.23(14) 4_556 . ? O1 Eu1 O11 129.85(15) 7_566 . ? O2 Eu1 O11 73.16(14) . . ? O5 Eu1 O11 140.30(15) 6_565 . ? O10 Eu1 O11 73.54(19) . . ? O6 Eu1 O7 99.46(12) 4_556 3_454 ? O1 Eu1 O7 77.11(12) 7_566 3_454 ? O2 Eu1 O7 145.81(11) . 3_454 ? O5 Eu1 O7 127.59(12) 6_565 3_454 ? O10 Eu1 O7 84.37(15) . 3_454 ? O11 Eu1 O7 73.77(13) . 3_454 ? O6 Eu1 O8 136.04(11) 4_556 3_454 ? O1 Eu1 O8 70.26(12) 7_566 3_454 ? O2 Eu1 O8 142.67(11) . 3_454 ? O5 Eu1 O8 74.81(11) 6_565 3_454 ? O10 Eu1 O8 72.26(15) . 3_454 ? O11 Eu1 O8 118.00(14) . 3_454 ? O7 Eu1 O8 52.90(11) 3_454 3_454 ? O6 Eu1 C14 117.48(13) 4_556 3_454 ? O1 Eu1 C14 68.62(13) 7_566 3_454 ? O2 Eu1 C14 158.07(13) . 3_454 ? O5 Eu1 C14 101.25(13) 6_565 3_454 ? O10 Eu1 C14 80.01(15) . 3_454 ? O11 Eu1 C14 97.88(15) . 3_454 ? O7 Eu1 C14 26.76(13) 3_454 3_454 ? O8 Eu1 C14 26.48(12) 3_454 3_454 ? O6 Eu1 O6 74.61(12) 4_556 6_565 ? O1 Eu1 O6 70.12(12) 7_566 6_565 ? O2 Eu1 O6 66.52(11) . 6_565 ? O5 Eu1 O6 48.95(11) 6_565 6_565 ? O10 Eu1 O6 119.04(15) . 6_565 ? O11 Eu1 O6 132.73(13) . 6_565 ? O7 Eu1 O6 146.82(11) 3_454 6_565 ? O8 Eu1 O6 109.01(10) 3_454 6_565 ? C14 Eu1 O6 128.29(12) 3_454 6_565 ? O6 Eu1 C15 99.37(13) 4_556 6_565 ? O1 Eu1 C15 81.72(14) 7_566 6_565 ? O2 Eu1 C15 66.93(12) . 6_565 ? O5 Eu1 C15 24.20(12) 6_565 6_565 ? O10 Eu1 C15 96.01(17) . 6_565 ? O11 Eu1 C15 140.05(14) . 6_565 ? O7 Eu1 C15 144.89(12) 3_454 6_565 ? O8 Eu1 C15 93.65(12) 3_454 6_565 ? C14 Eu1 C15 118.59(13) 3_454 6_565 ? O6 Eu1 C15 25.04(11) 6_565 6_565 ? C2 C1 C6 118.5(5) . . ? C2 C1 C13 120.8(4) . . ? C6 C1 C13 120.7(5) . . ? C1 C2 C3 120.7(5) . . ? C2 C3 C4 120.0(5) . . ? C2 C3 N1 117.6(5) . . ? C4 C3 N1 122.5(5) . . ? C5 C4 O9 118.0(5) . . ? C5 C4 C3 119.3(5) . . ? O9 C4 C3 122.7(5) . . ? C6 C5 C4 120.8(5) . . ? C5 C6 C1 120.7(5) . . ? C8 C7 C12 120.9(5) . . ? C8 C7 O9 116.6(4) . . ? C12 C7 O9 122.5(4) . . ? C7 C8 C9 119.4(4) . . ? C10 C9 C8 120.2(4) . . ? C10 C9 C14 120.5(4) . . ? C8 C9 C14 119.2(4) . . ? C11 C10 C9 119.3(4) . . ? C12 C11 C10 120.4(4) . . ? C12 C11 C15 117.9(4) . . ? C10 C11 C15 121.8(4) . . ? C7 C12 C11 119.8(4) . . ? O1 C13 O2 126.7(5) . . ? O1 C13 C1 116.1(4) . . ? O2 C13 C1 117.2(4) . . ? O8 C14 O7 122.1(4) . . ? O8 C14 C9 119.2(4) . . ? O7 C14 C9 118.7(4) . . ? O8 C14 Eu1 63.4(2) . 3_546 ? O7 C14 Eu1 59.9(2) . 3_546 ? C9 C14 Eu1 167.3(3) . 3_546 ? O5 C15 O6 122.2(4) . . ? O5 C15 C11 118.0(4) . . ? O6 C15 C11 119.8(4) . . ? O5 C15 Eu1 52.5(2) . 6_566 ? O6 C15 Eu1 70.9(3) . 6_566 ? C11 C15 Eu1 164.6(3) . 6_566 ? O10 C16 N2 132.5(7) . . ? O11 C19 N3 123.8(7) . . ? O4 N1 O3 123.4(5) . . ? O4 N1 C3 118.9(5) . . ? O3 N1 C3 117.7(5) . . ? C16 N2 C18 117.3(6) . . ? C16 N2 C17 123.0(8) . . ? C18 N2 C17 115.7(8) . . ? C16 N2 C17' 128.4(8) . . ? C18 N2 C17' 107.2(7) . . ? C17 N2 C17' 46.1(9) . . ? C19 N3 C21 121.0(6) . . ? C19 N3 C20 120.8(6) . . ? C21 N3 C20 118.1(5) . . ? C13 O1 Eu1 140.8(3) . 7_566 ? C13 O2 Eu1 135.7(3) . . ? C15 O5 Eu1 103.3(3) . 6_566 ? C15 O6 Eu1 167.3(3) . 4_546 ? C15 O6 Eu1 84.1(3) . 6_566 ? Eu1 O6 Eu1 105.39(12) 4_546 6_566 ? C14 O7 Eu1 93.4(3) . 3_546 ? C14 O8 Eu1 90.1(3) . 3_546 ? C4 O9 C7 115.2(4) . . ? C16 O10 Eu1 133.3(5) . . ? C19 O11 Eu1 139.1(4) . . ? _diffrn_measured_fraction_theta_max 0.996 _diffrn_reflns_theta_full 26.05 _diffrn_measured_fraction_theta_full 0.996 _refine_diff_density_max 2.947 _refine_diff_density_min -2.512 _refine_diff_density_rms 0.135 data_7 _database_code_depnum_ccdc_archive 'CCDC 857008' #TrackingRef '- 1-12 and 7.CIF' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point 'not measured' _chemical_formula_moiety 'C21 H20.50 Gd N3 O11.25' _chemical_formula_sum 'C21 H20.50 Gd N3 O11.25' _chemical_formula_weight 652.15 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 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' Gd Gd -0.1653 3.9035 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Monoclinic _symmetry_space_group_name_H-M C2/c loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y, -z+1/2' 'x+1/2, y+1/2, z' '-x+1/2, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y, z-1/2' '-x+1/2, -y+1/2, -z' 'x+1/2, -y+1/2, z-1/2' _cell_length_a 23.5619(12) _cell_length_b 15.6714(8) _cell_length_c 16.1158(8) _cell_angle_alpha 90.00 _cell_angle_beta 124.2380(10) _cell_angle_gamma 90.00 _cell_volume 4919.5(4) _cell_formula_units_Z 8 _cell_measurement_temperature 185(2) _cell_measurement_reflns_used 4927 _cell_measurement_theta_min 1.82 _cell_measurement_theta_max 26.15 _exptl_crystal_description rod _exptl_crystal_colour 'light yellow' _exptl_crystal_size_max 0.26 _exptl_crystal_size_mid 0.25 _exptl_crystal_size_min 0.21 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.761 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 2572 _exptl_absorpt_coefficient_mu 2.761 _exptl_absorpt_correction_type empirical _exptl_absorpt_correction_T_min 0.5338 _exptl_absorpt_correction_T_max 0.5948 _exptl_absorpt_process_details SADABS _exptl_special_details ; ? ; _diffrn_ambient_temperature 185(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'CCD area detector' _diffrn_measurement_method 'phi and omega scans' _diffrn_detector_area_resol_mean 9.00cm _diffrn_standards_number none _diffrn_standards_interval_count none _diffrn_standards_interval_time none _diffrn_standards_decay_% none _diffrn_reflns_number 13538 _diffrn_reflns_av_R_equivalents 0.0262 _diffrn_reflns_av_sigmaI/netI 0.0308 _diffrn_reflns_limit_h_min -27 _diffrn_reflns_limit_h_max 29 _diffrn_reflns_limit_k_min -19 _diffrn_reflns_limit_k_max 17 _diffrn_reflns_limit_l_min -19 _diffrn_reflns_limit_l_max 17 _diffrn_reflns_theta_min 1.82 _diffrn_reflns_theta_max 26.15 _reflns_number_total 4927 _reflns_number_gt 4304 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SMART' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics SHELXP-97 _computing_publication_material SHELXTL _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0315P)^2^+33.6846P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 4927 _refine_ls_number_parameters 292 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0376 _refine_ls_R_factor_gt 0.0318 _refine_ls_wR_factor_ref 0.0771 _refine_ls_wR_factor_gt 0.0741 _refine_ls_goodness_of_fit_ref 1.046 _refine_ls_restrained_S_all 1.046 _refine_ls_shift/su_max 0.001 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group Gd1 Gd 0.189701(9) 0.827867(12) 0.377765(13) 0.01513(7) Uani 1 1 d . . . C1 C 0.4025(2) 0.7759(3) 0.4711(3) 0.0194(8) Uani 1 1 d . . . C2 C 0.4556(2) 0.7414(3) 0.5612(3) 0.0209(9) Uani 1 1 d . . . H2A H 0.4470 0.7197 0.6082 0.025 Uiso 1 1 calc R . . C3 C 0.5215(2) 0.7387(3) 0.5823(3) 0.0201(8) Uani 1 1 d . . . C4 C 0.5343(2) 0.7723(3) 0.5142(3) 0.0210(9) Uani 1 1 d . . . H4A H 0.5792 0.7701 0.5281 0.025 Uiso 1 1 calc R . . C5 C 0.4814(2) 0.8087(3) 0.4267(3) 0.0230(9) Uani 1 1 d . . . C6 C 0.4152(2) 0.8108(3) 0.4041(3) 0.0239(9) Uani 1 1 d . . . H6A H 0.3790 0.8360 0.3434 0.029 Uiso 1 1 calc R . . C7 C 0.4536(2) 0.9053(3) 0.2979(3) 0.0254(10) Uani 1 1 d . . . C8 C 0.3992(2) 0.8896(3) 0.1991(3) 0.0245(9) Uani 1 1 d . . . C9 C 0.3577(2) 0.9556(3) 0.1381(3) 0.0234(9) Uani 1 1 d . . . H9A H 0.3211 0.9443 0.0707 0.028 Uiso 1 1 calc R . . C10 C 0.3693(2) 1.0383(3) 0.1748(3) 0.0222(9) Uani 1 1 d . . . C11 C 0.4248(2) 1.0540(3) 0.2725(3) 0.0314(10) Uani 1 1 d . . . H11A H 0.4340 1.1106 0.2980 0.038 Uiso 1 1 calc R . . C12 C 0.4667(2) 0.9878(3) 0.3330(3) 0.0316(10) Uani 1 1 d . . . H12A H 0.5048 0.9995 0.3993 0.038 Uiso 1 1 calc R . . C13 C 0.3297(2) 0.7766(3) 0.4421(3) 0.0200(8) Uani 1 1 d . . . C14 C 0.5800(2) 0.7030(3) 0.6795(3) 0.0183(8) Uani 1 1 d . . . C15 C 0.3215(2) 1.1094(3) 0.1110(3) 0.0220(9) Uani 1 1 d . . . C19 C 0.0753(3) 0.9564(4) 0.3877(5) 0.0480(6) Uani 1 1 d . A . H19A H 0.0379 0.9209 0.3413 0.058 Uiso 1 1 calc R . . C20 C -0.0093(3) 1.0544(4) 0.3709(5) 0.0480(6) Uani 1 1 d . . . H20A H -0.0404 1.0087 0.3277 0.072 Uiso 1 1 calc R . . H20B H -0.0197 1.1066 0.3313 0.072 Uiso 1 1 calc R . . H20C H -0.0154 1.0650 0.4254 0.072 Uiso 1 1 calc R . . C21 C 0.1163(3) 1.0869(4) 0.4812(5) 0.0480(6) Uani 1 1 d . . . H21A H 0.1606 1.0610 0.5038 0.072 Uiso 1 1 calc R . . H21B H 0.1143 1.0980 0.5394 0.072 Uiso 1 1 calc R . . H21C H 0.1111 1.1406 0.4465 0.072 Uiso 1 1 calc R . . N1 N 0.3832(2) 0.8038(3) 0.1562(3) 0.0371(10) Uani 1 1 d . . . N2 N 0.2298(3) 1.0817(3) 0.2830(4) 0.0503(7) Uani 1 1 d . . . N3 N 0.0613(2) 1.0290(3) 0.4130(4) 0.0480(6) Uani 1 1 d . . . O1 O 0.28590(14) 0.8164(2) 0.3647(2) 0.0269(7) Uani 1 1 d . . . O2 O 0.31456(15) 0.73732(19) 0.4955(2) 0.0239(6) Uani 1 1 d . . . O3 O 0.56901(14) 0.67856(19) 0.7444(2) 0.0233(6) Uani 1 1 d . . . O4 O 0.63855(14) 0.6999(2) 0.6959(2) 0.0224(6) Uani 1 1 d . . . O5 O 0.4056(3) 0.7424(2) 0.2120(3) 0.0640(13) Uani 1 1 d . . . O6 O 0.3474(2) 0.7974(3) 0.0642(3) 0.0537(11) Uani 1 1 d . . . O7 O 0.27821(14) 1.09352(18) 0.0196(2) 0.0232(6) Uani 1 1 d . . . O8 O 0.32951(16) 1.17843(18) 0.1549(2) 0.0274(7) Uani 1 1 d . . . O9 O 0.49758(16) 0.8422(2) 0.3626(2) 0.0332(8) Uani 1 1 d . . . O10 O 0.1883(2) 0.9599(2) 0.3019(3) 0.0503(7) Uani 1 1 d . . . O11 O 0.1337(2) 0.9313(2) 0.4202(3) 0.0480(6) Uani 1 1 d . . . C16 C 0.2363(7) 1.0071(8) 0.3312(10) 0.0503(7) Uani 0.50 1 d P A 1 H16A H 0.2797 0.9921 0.3893 0.060 Uiso 0.50 1 calc PR A 1 C17 C 0.1901(6) 1.0744(7) 0.1701(7) 0.0503(7) Uani 0.60 1 d P A 1 H17A H 0.1788 1.0144 0.1504 0.075 Uiso 0.60 1 calc PR A 1 H17B H 0.2181 1.0964 0.1473 0.075 Uiso 0.60 1 calc PR A 1 H17C H 0.1477 1.1077 0.1393 0.075 Uiso 0.60 1 calc PR A 1 C18 C 0.2520(7) 1.1735(7) 0.3195(9) 0.0503(7) Uani 0.50 1 d P A 1 H18A H 0.2128 1.2055 0.3095 0.075 Uiso 0.50 1 calc PR A 1 H18B H 0.2679 1.2005 0.2813 0.075 Uiso 0.50 1 calc PR A 1 H18C H 0.2892 1.1732 0.3910 0.075 Uiso 0.50 1 calc PR A 1 C16' C 0.2144(7) 1.0311(8) 0.3302(11) 0.0503(7) Uani 0.50 1 d P A 2 H16' H 0.2239 1.0505 0.3927 0.075 Uiso 0.50 1 calc PR A 2 C17' C 0.1759(8) 1.1046(10) 0.1962(11) 0.0503(7) Uani 0.40 1 d P A 2 H17D H 0.1563 1.0545 0.1524 0.075 Uiso 0.40 1 calc PR A 2 H17E H 0.1892 1.1470 0.1655 0.075 Uiso 0.40 1 calc PR A 2 H17F H 0.1417 1.1293 0.2056 0.075 Uiso 0.40 1 calc PR A 2 C18' C 0.2960(5) 1.1310(7) 0.3287(8) 0.0503(7) Uani 0.50 1 d P A 2 H18D H 0.3317 1.0935 0.3354 0.075 Uiso 0.50 1 calc PR A 2 H18E H 0.3104 1.1521 0.3951 0.075 Uiso 0.50 1 calc PR A 2 H18F H 0.2889 1.1794 0.2853 0.075 Uiso 0.50 1 calc PR A 2 O1W O 0.2518(5) 0.8405(7) 0.1593(8) 0.083(7) Uani 0.25 1 d PR A 2 loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 Gd1 0.01256(10) 0.01620(11) 0.01302(11) -0.00080(8) 0.00501(8) -0.00114(7) C1 0.020(2) 0.022(2) 0.018(2) 0.0009(17) 0.0120(17) 0.0006(16) C2 0.019(2) 0.024(2) 0.020(2) 0.0020(17) 0.0110(17) -0.0006(16) C3 0.021(2) 0.020(2) 0.018(2) 0.0008(17) 0.0098(17) -0.0009(16) C4 0.017(2) 0.022(2) 0.025(2) 0.0032(18) 0.0119(18) 0.0016(16) C5 0.025(2) 0.023(2) 0.025(2) 0.0069(18) 0.0170(19) 0.0044(17) C6 0.020(2) 0.030(2) 0.020(2) 0.0079(18) 0.0097(18) 0.0082(17) C7 0.025(2) 0.031(2) 0.029(2) 0.017(2) 0.020(2) 0.0131(18) C8 0.029(2) 0.022(2) 0.027(2) 0.0024(18) 0.019(2) 0.0034(18) C9 0.023(2) 0.025(2) 0.021(2) 0.0029(18) 0.0120(18) 0.0015(17) C10 0.024(2) 0.021(2) 0.018(2) 0.0048(17) 0.0098(18) 0.0039(17) C11 0.033(3) 0.026(2) 0.024(2) 0.0033(19) 0.009(2) 0.005(2) C12 0.026(2) 0.039(3) 0.020(2) 0.005(2) 0.0069(19) 0.005(2) C13 0.020(2) 0.023(2) 0.017(2) -0.0034(17) 0.0107(17) -0.0038(16) C14 0.0176(19) 0.018(2) 0.0145(19) -0.0010(16) 0.0062(16) 0.0000(16) C15 0.021(2) 0.021(2) 0.021(2) 0.0053(17) 0.0098(18) 0.0037(17) C19 0.0463(13) 0.0414(13) 0.0552(14) -0.0060(11) 0.0278(11) 0.0109(10) C20 0.0463(13) 0.0414(13) 0.0552(14) -0.0060(11) 0.0278(11) 0.0109(10) C21 0.0463(13) 0.0414(13) 0.0552(14) -0.0060(11) 0.0278(11) 0.0109(10) N1 0.046(3) 0.026(2) 0.045(3) 0.0075(19) 0.028(2) 0.0088(19) N2 0.0616(18) 0.0381(15) 0.0445(14) 0.0039(12) 0.0257(13) -0.0164(12) N3 0.0463(13) 0.0414(13) 0.0552(14) -0.0060(11) 0.0278(11) 0.0109(10) O1 0.0156(14) 0.0420(19) 0.0200(15) 0.0082(14) 0.0082(13) 0.0051(13) O2 0.0265(16) 0.0262(16) 0.0258(16) -0.0004(13) 0.0188(14) -0.0022(13) O3 0.0164(14) 0.0340(17) 0.0162(14) 0.0070(13) 0.0071(12) 0.0003(12) O4 0.0165(14) 0.0313(16) 0.0176(14) 0.0015(13) 0.0086(12) 0.0020(12) O5 0.111(4) 0.023(2) 0.059(3) 0.014(2) 0.048(3) 0.018(2) O6 0.062(3) 0.035(2) 0.042(2) -0.0050(18) 0.016(2) 0.0058(19) O7 0.0216(15) 0.0206(15) 0.0171(14) 0.0017(12) 0.0045(13) 0.0033(12) O8 0.0348(17) 0.0192(16) 0.0169(14) 0.0013(12) 0.0077(13) 0.0045(13) O9 0.0274(17) 0.044(2) 0.0378(19) 0.0275(16) 0.0239(15) 0.0195(15) O10 0.0616(18) 0.0381(15) 0.0445(14) 0.0039(12) 0.0257(13) -0.0164(12) O11 0.0463(13) 0.0414(13) 0.0552(14) -0.0060(11) 0.0278(11) 0.0109(10) C16 0.0616(18) 0.0381(15) 0.0445(14) 0.0039(12) 0.0257(13) -0.0164(12) C17 0.0616(18) 0.0381(15) 0.0445(14) 0.0039(12) 0.0257(13) -0.0164(12) C18 0.0616(18) 0.0381(15) 0.0445(14) 0.0039(12) 0.0257(13) -0.0164(12) C16' 0.0616(18) 0.0381(15) 0.0445(14) 0.0039(12) 0.0257(13) -0.0164(12) C17' 0.0616(18) 0.0381(15) 0.0445(14) 0.0039(12) 0.0257(13) -0.0164(12) C18' 0.0616(18) 0.0381(15) 0.0445(14) 0.0039(12) 0.0257(13) -0.0164(12) O1W 0.057(12) 0.128(19) 0.074(13) 0.039(13) 0.043(11) -0.011(12) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag Gd1 O2 2.336(3) 7_566 ? Gd1 O8 2.387(3) 4_545 ? Gd1 O7 2.393(3) 6_576 ? Gd1 O10 2.394(4) . ? Gd1 O1 2.398(3) . ? Gd1 O3 2.416(3) 8_465 ? Gd1 O11 2.419(4) . ? Gd1 O4 2.501(3) 8_465 ? Gd1 C14 2.798(4) 8_465 ? Gd1 O2 2.826(3) . ? Gd1 C13 2.958(4) . ? C1 C6 1.385(6) . ? C1 C2 1.386(6) . ? C1 C13 1.504(5) . ? C2 C3 1.391(6) . ? C3 C4 1.395(6) . ? C3 C14 1.496(5) . ? C4 C5 1.375(6) . ? C5 C6 1.388(6) . ? C5 O9 1.390(5) . ? C7 C12 1.374(7) . ? C7 O9 1.388(5) . ? C7 C8 1.393(6) . ? C8 C9 1.383(6) . ? C8 N1 1.461(6) . ? C9 C10 1.386(6) . ? C10 C11 1.391(6) . ? C10 C15 1.504(6) . ? C11 C12 1.385(6) . ? C13 O1 1.250(5) . ? C13 O2 1.260(5) . ? C14 O4 1.251(5) . ? C14 O3 1.269(5) . ? C14 Gd1 2.798(4) 8_566 ? C15 O8 1.248(5) . ? C15 O7 1.257(5) . ? C19 O11 1.229(6) . ? C19 N3 1.312(7) . ? C20 N3 1.455(7) . ? C21 N3 1.451(7) . ? N1 O5 1.216(5) . ? N1 O6 1.230(6) . ? N2 C16' 1.285(13) . ? N2 C17' 1.303(16) . ? N2 C16 1.363(13) . ? N2 C18' 1.509(10) . ? N2 C17 1.511(11) . ? N2 C18 1.530(12) . ? O2 Gd1 2.336(3) 7_566 ? O3 Gd1 2.416(3) 8_566 ? O4 Gd1 2.501(3) 8_566 ? O7 Gd1 2.393(3) 6_575 ? O8 Gd1 2.387(3) 4 ? O10 C16 1.203(13) . ? O10 C16' 1.231(13) . ? 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 O2 Gd1 O8 70.60(10) 7_566 4_545 ? O2 Gd1 O7 80.37(10) 7_566 6_576 ? O8 Gd1 O7 132.13(10) 4_545 6_576 ? O2 Gd1 O10 146.04(13) 7_566 . ? O8 Gd1 O10 142.08(12) 4_545 . ? O7 Gd1 O10 78.29(12) 6_576 . ? O2 Gd1 O1 123.49(10) 7_566 . ? O8 Gd1 O1 88.78(11) 4_545 . ? O7 Gd1 O1 76.32(10) 6_576 . ? O10 Gd1 O1 76.21(13) . . ? O2 Gd1 O3 98.72(10) 7_566 8_465 ? O8 Gd1 O3 77.33(10) 4_545 8_465 ? O7 Gd1 O3 145.89(10) 6_576 8_465 ? O10 Gd1 O3 84.89(12) . 8_465 ? O1 Gd1 O3 128.05(10) . 8_465 ? O2 Gd1 O11 75.35(12) 7_566 . ? O8 Gd1 O11 130.82(13) 4_545 . ? O7 Gd1 O11 72.91(12) 6_576 . ? O10 Gd1 O11 73.29(14) . . ? O1 Gd1 O11 140.16(13) . . ? O3 Gd1 O11 73.92(12) 8_465 . ? O2 Gd1 O4 135.98(10) 7_566 8_465 ? O8 Gd1 O4 70.39(10) 4_545 8_465 ? O7 Gd1 O4 142.67(10) 6_576 8_465 ? O10 Gd1 O4 72.12(12) . 8_465 ? O1 Gd1 O4 74.95(9) . 8_465 ? O3 Gd1 O4 53.16(9) 8_465 8_465 ? O11 Gd1 O4 117.88(12) . 8_465 ? O2 Gd1 C14 117.15(11) 7_566 8_465 ? O8 Gd1 C14 68.89(11) 4_545 8_465 ? O7 Gd1 C14 158.17(11) 6_576 8_465 ? O10 Gd1 C14 80.10(12) . 8_465 ? O1 Gd1 C14 101.45(11) . 8_465 ? O3 Gd1 C14 26.92(11) 8_465 8_465 ? O11 Gd1 C14 97.93(13) . 8_465 ? O4 Gd1 C14 26.56(10) 8_465 8_465 ? O2 Gd1 O2 74.59(10) 7_566 . ? O8 Gd1 O2 69.64(10) 4_545 . ? O7 Gd1 O2 66.35(9) 6_576 . ? O10 Gd1 O2 119.11(12) . . ? O1 Gd1 O2 48.93(9) . . ? O3 Gd1 O2 146.70(9) 8_465 . ? O11 Gd1 O2 132.40(11) . . ? O4 Gd1 O2 109.42(9) 8_465 . ? C14 Gd1 O2 128.57(10) 8_465 . ? O2 Gd1 C13 99.35(11) 7_566 . ? O8 Gd1 C13 81.18(11) 4_545 . ? O7 Gd1 C13 66.69(11) 6_576 . ? O10 Gd1 C13 96.07(13) . . ? O1 Gd1 C13 24.22(10) . . ? O3 Gd1 C13 145.35(10) 8_465 . ? O11 Gd1 C13 139.55(12) . . ? O4 Gd1 C13 94.06(10) 8_465 . ? C14 Gd1 C13 119.01(11) 8_465 . ? O2 Gd1 C13 25.04(10) . . ? C6 C1 C2 120.5(4) . . ? C6 C1 C13 117.6(4) . . ? C2 C1 C13 121.9(4) . . ? C1 C2 C3 119.6(4) . . ? C2 C3 C4 120.2(4) . . ? C2 C3 C14 120.7(4) . . ? C4 C3 C14 119.0(4) . . ? C5 C4 C3 119.3(4) . . ? C4 C5 C6 121.2(4) . . ? C4 C5 O9 116.6(4) . . ? C6 C5 O9 122.2(4) . . ? C1 C6 C5 119.3(4) . . ? C12 C7 O9 117.5(4) . . ? C12 C7 C8 119.1(4) . . ? O9 C7 C8 123.4(4) . . ? C9 C8 C7 120.5(4) . . ? C9 C8 N1 117.4(4) . . ? C7 C8 N1 122.0(4) . . ? C8 C9 C10 120.4(4) . . ? C9 C10 C11 118.8(4) . . ? C9 C10 C15 120.6(4) . . ? C11 C10 C15 120.6(4) . . ? C12 C11 C10 120.5(4) . . ? C7 C12 C11 120.6(4) . . ? O1 C13 O2 122.3(4) . . ? O1 C13 C1 118.1(4) . . ? O2 C13 C1 119.7(4) . . ? O1 C13 Gd1 51.9(2) . . ? O2 C13 Gd1 71.6(2) . . ? C1 C13 Gd1 164.5(3) . . ? O4 C14 O3 121.7(4) . . ? O4 C14 C3 119.5(4) . . ? O3 C14 C3 118.7(4) . . ? O4 C14 Gd1 63.4(2) . 8_566 ? O3 C14 Gd1 59.5(2) . 8_566 ? C3 C14 Gd1 167.3(3) . 8_566 ? O8 C15 O7 126.9(4) . . ? O8 C15 C10 116.0(4) . . ? O7 C15 C10 117.1(4) . . ? O11 C19 N3 124.2(6) . . ? O5 N1 O6 123.0(5) . . ? O5 N1 C8 119.3(4) . . ? O6 N1 C8 117.8(4) . . ? C16' N2 C17' 112.0(10) . . ? C16' N2 C16 27.4(8) . . ? C17' N2 C16 125.1(9) . . ? C16' N2 C18' 125.9(8) . . ? C17' N2 C18' 119.9(8) . . ? C16 N2 C18' 114.1(8) . . ? C16' N2 C17 118.5(8) . . ? C17' N2 C17 32.8(8) . . ? C16 N2 C17 114.6(8) . . ? C18' N2 C17 113.3(6) . . ? C16' N2 C18 120.1(9) . . ? C17' N2 C18 94.0(9) . . ? C16 N2 C18 133.0(8) . . ? C18' N2 C18 45.3(6) . . ? C17 N2 C18 112.3(7) . . ? C19 N3 C21 120.3(5) . . ? C19 N3 C20 120.9(5) . . ? C21 N3 C20 118.8(4) . . ? C13 O1 Gd1 103.9(2) . . ? C13 O2 Gd1 167.8(3) . 7_566 ? C13 O2 Gd1 83.3(2) . . ? Gd1 O2 Gd1 105.42(10) 7_566 . ? C14 O3 Gd1 93.5(2) . 8_566 ? C14 O4 Gd1 90.1(2) . 8_566 ? C15 O7 Gd1 135.5(3) . 6_575 ? C15 O8 Gd1 140.9(3) . 4 ? C7 O9 C5 115.2(3) . . ? C16 O10 C16' 30.1(8) . . ? C16 O10 Gd1 126.3(7) . . ? C16' O10 Gd1 137.2(7) . . ? C19 O11 Gd1 138.8(4) . . ? O10 C16 N2 121.7(12) . . ? O10 C16' N2 126.0(12) . . ? _diffrn_measured_fraction_theta_max 0.998 _diffrn_reflns_theta_full 26.15 _diffrn_measured_fraction_theta_full 0.998 _refine_diff_density_max 2.002 _refine_diff_density_min -2.015 _refine_diff_density_rms 0.116 data_8 _database_code_depnum_ccdc_archive 'CCDC 857009' #TrackingRef '- 1-12 and 7.CIF' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point 'not measured' _chemical_formula_moiety 'C21 H20.50 N3 O11.25 Tb' _chemical_formula_sum 'C21 H20.50 N3 O11.25 Tb' _chemical_formula_weight 653.83 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Tb Tb -0.1723 4.1537 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Monoclinic _symmetry_space_group_name_H-M C2/c loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y, -z+1/2' 'x+1/2, y+1/2, z' '-x+1/2, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y, z-1/2' '-x+1/2, -y+1/2, -z' 'x+1/2, -y+1/2, z-1/2' _cell_length_a 23.5862(9) _cell_length_b 15.7079(6) _cell_length_c 16.0933(12) _cell_angle_alpha 90.00 _cell_angle_beta 124.16 _cell_angle_gamma 90.00 _cell_volume 4933.7(5) _cell_formula_units_Z 8 _cell_measurement_temperature 185(2) _cell_measurement_reflns_used 4916 _cell_measurement_theta_min 1.66 _cell_measurement_theta_max 26.11 _exptl_crystal_description rod _exptl_crystal_colour 'light yellow' _exptl_crystal_size_max 0.25 _exptl_crystal_size_mid 0.18 _exptl_crystal_size_min 0.13 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.760 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 2579 _exptl_absorpt_coefficient_mu 2.931 _exptl_absorpt_correction_type empirical _exptl_absorpt_correction_T_min 0.5277 _exptl_absorpt_correction_T_max 0.7018 _exptl_absorpt_process_details SADABS _exptl_special_details ; ? ; _diffrn_ambient_temperature 185(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'CCD area detector' _diffrn_measurement_method 'phi and omega scans' _diffrn_detector_area_resol_mean 9.00cm _diffrn_standards_number none _diffrn_standards_interval_count none _diffrn_standards_interval_time none _diffrn_standards_decay_% none _diffrn_reflns_number 13466 _diffrn_reflns_av_R_equivalents 0.0209 _diffrn_reflns_av_sigmaI/netI 0.0243 _diffrn_reflns_limit_h_min -20 _diffrn_reflns_limit_h_max 29 _diffrn_reflns_limit_k_min -19 _diffrn_reflns_limit_k_max 19 _diffrn_reflns_limit_l_min -19 _diffrn_reflns_limit_l_max 19 _diffrn_reflns_theta_min 1.66 _diffrn_reflns_theta_max 26.11 _reflns_number_total 4916 _reflns_number_gt 4445 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SMART' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics SHELXP-97 _computing_publication_material SHELXTL _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0364P)^2^+55.5784P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 4916 _refine_ls_number_parameters 289 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0380 _refine_ls_R_factor_gt 0.0342 _refine_ls_wR_factor_ref 0.0851 _refine_ls_wR_factor_gt 0.0827 _refine_ls_goodness_of_fit_ref 1.043 _refine_ls_restrained_S_all 1.043 _refine_ls_shift/su_max 0.001 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group Tb1 Tb 0.310550(10) -0.827609(12) 0.123129(14) 0.01415(8) Uani 1 1 d . . . C1 C 0.3683(2) -0.5388(3) 0.1737(3) 0.0236(10) Uani 1 1 d . . . C2 C 0.3568(2) -0.4566(3) 0.1366(4) 0.0232(10) Uani 1 1 d . . . H2A H 0.3203 -0.4454 0.0690 0.028 Uiso 1 1 calc R . . C3 C 0.3983(2) -0.3903(3) 0.1979(4) 0.0223(10) Uani 1 1 d . . . C4 C 0.4527(2) -0.4062(3) 0.2969(4) 0.0256(10) Uani 1 1 d . . . C5 C 0.4654(3) -0.4891(4) 0.3321(4) 0.0316(11) Uani 1 1 d . . . H5 H 0.5032 -0.5008 0.3986 0.038 Uiso 1 1 calc R . . C6 C 0.4238(3) -0.5549(3) 0.2718(4) 0.0308(11) Uani 1 1 d . . . H6A H 0.4330 -0.6114 0.2971 0.037 Uiso 1 1 calc R . . C7 C 0.4805(2) -0.3088(3) 0.4252(4) 0.0229(10) Uani 1 1 d . . . C8 C 0.4149(2) -0.3103(3) 0.4036(3) 0.0217(9) Uani 1 1 d . . . H8A H 0.3785 -0.3352 0.3430 0.026 Uiso 1 1 calc R . . C9 C 0.4027(2) -0.2753(3) 0.4711(3) 0.0180(9) Uani 1 1 d . . . C10 C 0.4561(2) -0.2411(3) 0.5614(3) 0.0179(9) Uani 1 1 d . . . H10A H 0.4479 -0.2193 0.6088 0.022 Uiso 1 1 calc R . . C11 C 0.5218(2) -0.2391(3) 0.5815(3) 0.0174(9) Uani 1 1 d . . . C12 C 0.5341(2) -0.2725(3) 0.5128(3) 0.0193(9) Uani 1 1 d . . . H12A H 0.5787 -0.2705 0.5261 0.023 Uiso 1 1 calc R . . C13 C 0.3204(2) -0.6103(3) 0.1097(3) 0.0208(9) Uani 1 1 d . . . C14 C 0.3302(2) -0.2753(3) 0.4434(3) 0.0192(9) Uani 1 1 d . . . C15 C 0.5807(2) -0.2039(3) 0.6796(3) 0.0178(9) Uani 1 1 d . . . C19 C 0.4244(3) -0.9564(4) 0.1135(5) 0.0481(6) Uani 1 1 d . . . H19A H 0.4616 -0.9206 0.1595 0.058 Uiso 1 1 calc R . . C20 C 0.5095(3) -1.0532(4) 0.1300(5) 0.0481(6) Uani 1 1 d . . . H20A H 0.5404 -1.0077 0.1737 0.072 Uiso 1 1 calc R . . H20B H 0.5155 -1.0630 0.0753 0.072 Uiso 1 1 calc R . . H20C H 0.5201 -1.1056 0.1692 0.072 Uiso 1 1 calc R . . C21 C 0.3842(3) -1.0875(4) 0.0204(5) 0.0481(6) Uani 1 1 d . . . H21A H 0.3397 -1.0628 -0.0015 0.072 Uiso 1 1 calc R . . H21B H 0.3904 -1.1413 0.0554 0.072 Uiso 1 1 calc R . . H21C H 0.3859 -1.0980 -0.0382 0.072 Uiso 1 1 calc R . . C16 C 0.2723(4) -1.0153(4) 0.1707(5) 0.0579(8) Uani 1 1 d . A . H16 H 0.2366 -1.0136 0.1012 0.087 Uiso 1 1 calc R . . C18 C 0.3165(4) -1.0829(5) 0.3244(5) 0.0579(8) Uani 1 1 d . A . H18A H 0.3313 -1.0250 0.3504 0.087 Uiso 1 1 calc R . . H18B H 0.3566 -1.1173 0.3425 0.087 Uiso 1 1 calc R . . H18C H 0.2936 -1.1083 0.3537 0.087 Uiso 1 1 calc R . . C17' C 0.2488(10) -1.1722(10) 0.1817(12) 0.0579(8) Uani 0.45 1 d P A 1 H17A H 0.2881 -1.2037 0.1917 0.087 Uiso 0.45 1 calc PR A 1 H17B H 0.2116 -1.1722 0.1102 0.087 Uiso 0.45 1 calc PR A 1 H17C H 0.2330 -1.1995 0.2200 0.087 Uiso 0.45 1 calc PR A 1 C17 C 0.2049(7) -1.1303(9) 0.1721(9) 0.0579(8) Uani 0.55 1 d P A 2 H17D H 0.1688 -1.0937 0.1650 0.087 Uiso 0.55 1 calc PR A 2 H17E H 0.2123 -1.1787 0.2155 0.087 Uiso 0.55 1 calc PR A 2 H17F H 0.1910 -1.1512 0.1058 0.087 Uiso 0.55 1 calc PR A 2 N1 N 0.3826(3) -0.3053(3) 0.1545(4) 0.0347(10) Uani 1 1 d . . . N3 N 0.4388(3) -1.0285(3) 0.0883(4) 0.0481(6) Uani 1 1 d . . . N2 N 0.2703(3) -1.0801(4) 0.2180(4) 0.0579(8) Uani 1 1 d . . . O1 O 0.32793(18) -0.6789(2) 0.1545(3) 0.0263(7) Uani 1 1 d . . . O2 O 0.27744(16) -0.5947(2) 0.0183(2) 0.0225(7) Uani 1 1 d . . . O3 O 0.3475(2) -0.2987(3) 0.0632(3) 0.0503(11) Uani 1 1 d . . . O4 O 0.4047(3) -0.2438(3) 0.2110(4) 0.0630(15) Uani 1 1 d . . . O5 O 0.28568(16) -0.3144(2) 0.3659(2) 0.0249(7) Uani 1 1 d . . . O6 O 0.31630(16) -0.2362(2) 0.4982(2) 0.0228(7) Uani 1 1 d . . . O7 O 0.56967(16) -0.1798(2) 0.7445(2) 0.0232(7) Uani 1 1 d . . . O8 O 0.63896(15) -0.2008(2) 0.6956(2) 0.0212(7) Uani 1 1 d . . . O9 O 0.49657(18) -0.3426(2) 0.3609(3) 0.0328(9) Uani 1 1 d . . . O11 O 0.3661(2) -0.9319(3) 0.0815(3) 0.0481(6) Uani 1 1 d . . . O10 O 0.3109(3) -0.9578(3) 0.1991(3) 0.0579(8) Uani 1 1 d . . . O1W O 0.2551(9) -1.3401(15) 0.1650(14) 0.061(6) Uani 0.25 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 Tb1 0.01131(11) 0.01499(12) 0.01220(12) -0.00084(7) 0.00419(9) -0.00117(7) C1 0.024(2) 0.025(2) 0.020(2) -0.0049(18) 0.011(2) -0.0033(19) C2 0.023(2) 0.024(2) 0.020(2) -0.0027(18) 0.011(2) -0.0022(19) C3 0.027(2) 0.020(2) 0.027(2) -0.0048(19) 0.019(2) -0.0041(19) C4 0.020(2) 0.033(3) 0.027(2) -0.016(2) 0.016(2) -0.012(2) C5 0.023(2) 0.038(3) 0.022(2) -0.005(2) 0.005(2) -0.003(2) C6 0.029(3) 0.026(3) 0.024(2) -0.002(2) 0.006(2) -0.005(2) C7 0.022(2) 0.026(2) 0.024(2) -0.0083(19) 0.015(2) -0.0051(19) C8 0.016(2) 0.029(2) 0.019(2) -0.0089(18) 0.0091(19) -0.0061(18) C9 0.015(2) 0.020(2) 0.018(2) 0.0008(17) 0.0092(18) 0.0013(17) C10 0.018(2) 0.019(2) 0.015(2) -0.0023(17) 0.0083(18) -0.0013(17) C11 0.015(2) 0.018(2) 0.015(2) 0.0001(17) 0.0057(18) -0.0004(16) C12 0.014(2) 0.021(2) 0.022(2) -0.0038(18) 0.0098(19) -0.0023(17) C13 0.020(2) 0.019(2) 0.018(2) -0.0037(17) 0.0074(19) -0.0019(17) C14 0.016(2) 0.023(2) 0.019(2) 0.0055(18) 0.0098(18) 0.0038(17) C15 0.016(2) 0.017(2) 0.015(2) 0.0015(17) 0.0059(18) 0.0015(17) C19 0.0480(14) 0.0412(14) 0.0563(15) -0.0058(11) 0.0299(13) 0.0104(11) C20 0.0480(14) 0.0412(14) 0.0563(15) -0.0058(11) 0.0299(13) 0.0104(11) C21 0.0480(14) 0.0412(14) 0.0563(15) -0.0058(11) 0.0299(13) 0.0104(11) C16 0.0683(19) 0.0482(16) 0.0429(15) 0.0055(12) 0.0224(14) -0.0255(14) C18 0.0683(19) 0.0482(16) 0.0429(15) 0.0055(12) 0.0224(14) -0.0255(14) C17' 0.0683(19) 0.0482(16) 0.0429(15) 0.0055(12) 0.0224(14) -0.0255(14) C17 0.0683(19) 0.0482(16) 0.0429(15) 0.0055(12) 0.0224(14) -0.0255(14) N1 0.042(3) 0.024(2) 0.040(3) -0.004(2) 0.024(2) -0.007(2) N3 0.0480(14) 0.0412(14) 0.0563(15) -0.0058(11) 0.0299(13) 0.0104(11) N2 0.0683(19) 0.0482(16) 0.0429(15) 0.0055(12) 0.0224(14) -0.0255(14) O1 0.0330(19) 0.0177(17) 0.0189(16) -0.0009(13) 0.0089(15) -0.0035(14) O2 0.0215(16) 0.0181(16) 0.0170(15) -0.0018(12) 0.0043(14) -0.0032(13) O3 0.056(3) 0.033(2) 0.042(3) 0.0028(19) 0.015(2) -0.005(2) O4 0.109(4) 0.026(2) 0.058(3) -0.014(2) 0.049(3) -0.018(2) O5 0.0121(15) 0.039(2) 0.0197(16) -0.0051(14) 0.0065(13) -0.0039(13) O6 0.0232(17) 0.0267(17) 0.0247(17) 0.0004(14) 0.0172(15) 0.0034(13) O7 0.0143(15) 0.0348(19) 0.0157(15) -0.0055(13) 0.0055(13) 0.0015(13) O8 0.0156(15) 0.0274(17) 0.0185(16) -0.0010(13) 0.0083(13) -0.0024(13) O9 0.0255(18) 0.046(2) 0.035(2) -0.0270(17) 0.0224(17) -0.0193(16) O11 0.0480(14) 0.0412(14) 0.0563(15) -0.0058(11) 0.0299(13) 0.0104(11) O10 0.0683(19) 0.0482(16) 0.0429(15) 0.0055(12) 0.0224(14) -0.0255(14) O1W 0.029(9) 0.112(17) 0.044(10) -0.037(11) 0.021(8) 0.000(10) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag Tb1 O6 2.318(3) 6_545 ? Tb1 O1 2.376(3) . ? Tb1 O10 2.380(4) . ? Tb1 O2 2.382(3) 7_535 ? Tb1 O5 2.382(3) 4_545 ? Tb1 O7 2.403(3) 5_646 ? Tb1 O11 2.416(4) . ? Tb1 O8 2.495(3) 5_646 ? Tb1 C15 2.785(4) 5_646 ? Tb1 O6 2.875(3) 4_545 ? C1 C2 1.384(7) . ? C1 C6 1.396(7) . ? C1 C13 1.514(6) . ? C2 C3 1.389(6) . ? C2 H2A 0.9500 . ? C3 C4 1.397(7) . ? C3 N1 1.455(6) . ? C4 C5 1.383(8) . ? C4 O9 1.391(5) . ? C5 C6 1.380(7) . ? C5 H5 0.9500 . ? C6 H6A 0.9500 . ? C7 C12 1.382(6) . ? C7 C8 1.382(6) . ? C7 O9 1.392(6) . ? C8 C9 1.384(6) . ? C8 H8A 0.9500 . ? C9 C10 1.389(6) . ? C9 C14 1.504(6) . ? C10 C11 1.395(6) . ? C10 H10A 0.9500 . ? C11 C12 1.392(6) . ? C11 C15 1.506(6) . ? C12 H12A 0.9500 . ? C13 O1 1.253(6) . ? C13 O2 1.256(5) . ? C14 O5 1.251(6) . ? C14 O6 1.261(5) . ? C15 O8 1.249(5) . ? C15 O7 1.267(5) . ? C15 Tb1 2.785(4) 5_646 ? C19 O11 1.228(7) . ? C19 N3 1.310(8) . ? C19 H19A 0.9500 . ? C20 N3 1.458(8) . ? C20 H20A 0.9800 . ? C20 H20B 0.9800 . ? C20 H20C 0.9800 . ? C21 N3 1.460(8) . ? C21 H21A 0.9800 . ? C21 H21B 0.9800 . ? C21 H21C 0.9800 . ? C16 O10 1.178(7) . ? C16 N2 1.288(8) . ? C16 H16 0.9500 . ? C18 N2 1.424(8) . ? C18 H18A 0.9800 . ? C18 H18B 0.9800 . ? C18 H18C 0.9800 . ? C17' N2 1.536(15) . ? C17' H17A 0.9800 . ? C17' H17B 0.9800 . ? C17' H17C 0.9800 . ? C17 N2 1.506(13) . ? C17 H17D 0.9800 . ? C17 H17E 0.9800 . ? C17 H17F 0.9800 . ? N1 O3 1.221(6) . ? N1 O4 1.225(6) . ? O2 Tb1 2.382(3) 7_535 ? O5 Tb1 2.382(3) 4 ? O6 Tb1 2.318(3) 6_546 ? O6 Tb1 2.875(3) 4 ? O7 Tb1 2.403(3) 5_646 ? O8 Tb1 2.495(3) 5_646 ? 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 O6 Tb1 O1 70.86(12) 6_545 . ? O6 Tb1 O10 146.29(15) 6_545 . ? O1 Tb1 O10 141.74(14) . . ? O6 Tb1 O2 80.59(11) 6_545 7_535 ? O1 Tb1 O2 131.34(11) . 7_535 ? O10 Tb1 O2 78.49(13) . 7_535 ? O6 Tb1 O5 123.29(11) 6_545 4_545 ? O1 Tb1 O5 87.51(12) . 4_545 ? O10 Tb1 O5 76.46(16) . 4_545 ? O2 Tb1 O5 76.12(11) 7_535 4_545 ? O6 Tb1 O7 97.82(11) 6_545 5_646 ? O1 Tb1 O7 77.74(12) . 5_646 ? O10 Tb1 O7 85.55(14) . 5_646 ? O2 Tb1 O7 146.29(11) 7_535 5_646 ? O5 Tb1 O7 128.67(11) 4_545 5_646 ? O6 Tb1 O11 75.37(14) 6_545 . ? O1 Tb1 O11 132.04(14) . . ? O10 Tb1 O11 73.36(18) . . ? O2 Tb1 O11 72.84(13) 7_535 . ? O5 Tb1 O11 140.12(14) 4_545 . ? O7 Tb1 O11 74.20(13) 5_646 . ? O6 Tb1 O8 135.64(11) 6_545 5_646 ? O1 Tb1 O8 70.35(11) . 5_646 ? O10 Tb1 O8 72.03(14) . 5_646 ? O2 Tb1 O8 142.81(11) 7_535 5_646 ? O5 Tb1 O8 75.35(11) 4_545 5_646 ? O7 Tb1 O8 53.34(10) 5_646 5_646 ? O11 Tb1 O8 117.93(13) . 5_646 ? O6 Tb1 C15 116.54(12) 6_545 5_646 ? O1 Tb1 C15 69.19(12) . 5_646 ? O10 Tb1 C15 80.31(14) . 5_646 ? O2 Tb1 C15 158.58(12) 7_535 5_646 ? O5 Tb1 C15 101.91(12) 4_545 5_646 ? O7 Tb1 C15 27.00(12) 5_646 5_646 ? O11 Tb1 C15 98.08(14) . 5_646 ? O8 Tb1 C15 26.64(11) 5_646 5_646 ? O6 Tb1 O6 74.95(11) 6_545 4_545 ? O1 Tb1 O6 69.08(11) . 4_545 ? O10 Tb1 O6 118.71(14) . 4_545 ? O2 Tb1 O6 65.84(10) 7_535 4_545 ? O5 Tb1 O6 48.34(10) 4_545 4_545 ? O7 Tb1 O6 146.63(10) 5_646 4_545 ? O11 Tb1 O6 132.07(12) . 4_545 ? O8 Tb1 O6 109.65(10) 5_646 4_545 ? C15 Tb1 O6 128.81(11) 5_646 4_545 ? C2 C1 C6 119.3(4) . . ? C2 C1 C13 120.5(4) . . ? C6 C1 C13 120.2(4) . . ? C1 C2 C3 120.2(4) . . ? C1 C2 H2A 119.9 . . ? C3 C2 H2A 119.9 . . ? C2 C3 C4 120.4(4) . . ? C2 C3 N1 117.3(4) . . ? C4 C3 N1 122.3(4) . . ? C5 C4 O9 118.2(5) . . ? C5 C4 C3 119.0(4) . . ? O9 C4 C3 122.8(5) . . ? C6 C5 C4 120.8(5) . . ? C6 C5 H5 119.6 . . ? C4 C5 H5 119.6 . . ? C5 C6 C1 120.3(5) . . ? C5 C6 H6A 119.8 . . ? C1 C6 H6A 119.8 . . ? C12 C7 C8 121.1(4) . . ? C12 C7 O9 116.1(4) . . ? C8 C7 O9 122.7(4) . . ? C7 C8 C9 119.5(4) . . ? C7 C8 H8A 120.2 . . ? C9 C8 H8A 120.2 . . ? C8 C9 C10 120.6(4) . . ? C8 C9 C14 118.0(4) . . ? C10 C9 C14 121.5(4) . . ? C9 C10 C11 119.2(4) . . ? C9 C10 H10A 120.4 . . ? C11 C10 H10A 120.4 . . ? C12 C11 C10 120.5(4) . . ? C12 C11 C15 119.4(4) . . ? C10 C11 C15 120.1(4) . . ? C7 C12 C11 119.1(4) . . ? C7 C12 H12A 120.4 . . ? C11 C12 H12A 120.4 . . ? O1 C13 O2 127.0(4) . . ? O1 C13 C1 115.9(4) . . ? O2 C13 C1 117.1(4) . . ? O5 C14 O6 122.2(4) . . ? O5 C14 C9 118.3(4) . . ? O6 C14 C9 119.4(4) . . ? O8 C15 O7 122.0(4) . . ? O8 C15 C11 119.4(4) . . ? O7 C15 C11 118.6(4) . . ? O8 C15 Tb1 63.6(2) . 5_646 ? O7 C15 Tb1 59.5(2) . 5_646 ? C11 C15 Tb1 167.9(3) . 5_646 ? O11 C19 N3 124.4(7) . . ? O11 C19 H19A 117.8 . . ? N3 C19 H19A 117.8 . . ? N3 C20 H20A 109.5 . . ? N3 C20 H20B 109.5 . . ? H20A C20 H20B 109.5 . . ? N3 C20 H20C 109.5 . . ? H20A C20 H20C 109.5 . . ? H20B C20 H20C 109.5 . . ? N3 C21 H21A 109.5 . . ? N3 C21 H21B 109.5 . . ? H21A C21 H21B 109.5 . . ? N3 C21 H21C 109.5 . . ? H21A C21 H21C 109.5 . . ? H21B C21 H21C 109.5 . . ? O10 C16 N2 130.8(7) . . ? O10 C16 H16 114.6 . . ? N2 C16 H16 114.6 . . ? N2 C18 H18A 109.5 . . ? N2 C18 H18B 109.5 . . ? H18A C18 H18B 109.5 . . ? N2 C18 H18C 109.5 . . ? H18A C18 H18C 109.5 . . ? H18B C18 H18C 109.5 . . ? N2 C17' H17A 109.5 . . ? N2 C17' H17B 109.5 . . ? H17A C17' H17B 109.5 . . ? N2 C17' H17C 109.5 . . ? H17A C17' H17C 109.5 . . ? H17B C17' H17C 109.5 . . ? N2 C17 H17D 109.5 . . ? N2 C17 H17E 109.5 . . ? H17D C17 H17E 109.5 . . ? N2 C17 H17F 109.5 . . ? H17D C17 H17F 109.5 . . ? H17E C17 H17F 109.5 . . ? O3 N1 O4 123.0(5) . . ? O3 N1 C3 118.3(4) . . ? O4 N1 C3 118.7(5) . . ? C19 N3 C20 121.1(6) . . ? C19 N3 C21 120.5(5) . . ? C20 N3 C21 118.4(5) . . ? C16 N2 C18 118.5(6) . . ? C16 N2 C17 119.4(7) . . ? C18 N2 C17 117.2(6) . . ? C16 N2 C17' 129.3(8) . . ? C18 N2 C17' 107.2(7) . . ? C17 N2 C17' 44.9(8) . . ? C13 O1 Tb1 140.5(3) . . ? C13 O2 Tb1 135.8(3) . 7_535 ? C14 O5 Tb1 105.7(3) . 4 ? C14 O6 Tb1 169.4(3) . 6_546 ? C14 O6 Tb1 82.1(3) . 4 ? Tb1 O6 Tb1 105.05(11) 6_546 4 ? C15 O7 Tb1 93.5(3) . 5_646 ? C15 O8 Tb1 89.8(3) . 5_646 ? C4 O9 C7 115.2(4) . . ? C19 O11 Tb1 138.6(4) . . ? C16 O10 Tb1 132.9(5) . . ? _diffrn_measured_fraction_theta_max 0.999 _diffrn_reflns_theta_full 26.11 _diffrn_measured_fraction_theta_full 0.999 _refine_diff_density_max 3.105 _refine_diff_density_min -2.635 _refine_diff_density_rms 0.131 data_9 _database_code_depnum_ccdc_archive 'CCDC 857010' #TrackingRef '- 1-12 and 7.CIF' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point 'not measured' _chemical_formula_moiety 'C21 H20.50 Dy N3 O11.25' _chemical_formula_sum 'C21 H20.50 Dy N3 O11.25' _chemical_formula_weight 657.40 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' Dy Dy -0.1892 4.4098 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Monoclinic _symmetry_space_group_name_H-M C2/c loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y, -z+1/2' 'x+1/2, y+1/2, z' '-x+1/2, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y, z-1/2' '-x+1/2, -y+1/2, -z' 'x+1/2, -y+1/2, z-1/2' _cell_length_a 23.571(4) _cell_length_b 15.673(3) _cell_length_c 16.082(3) _cell_angle_alpha 90.00 _cell_angle_beta 124.154(2) _cell_angle_gamma 90.00 _cell_volume 4916.5(14) _cell_formula_units_Z 8 _cell_measurement_temperature 185(2) _cell_measurement_reflns_used 4878 _cell_measurement_theta_min 1.67 _cell_measurement_theta_max 26.08 _exptl_crystal_description rod _exptl_crystal_colour 'light yellow' _exptl_crystal_size_max 0.16 _exptl_crystal_size_mid 0.13 _exptl_crystal_size_min 0.10 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.776 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 2588 _exptl_absorpt_coefficient_mu 3.104 _exptl_absorpt_correction_type empirical _exptl_absorpt_correction_T_min 0.6365 _exptl_absorpt_correction_T_max 0.7465 _exptl_absorpt_process_details SADABS _exptl_special_details ; ? ; _diffrn_ambient_temperature 185(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'CCD area detector' _diffrn_measurement_method 'phi and omega scans' _diffrn_detector_area_resol_mean 9.00cm _diffrn_standards_number none _diffrn_standards_interval_count none _diffrn_standards_interval_time none _diffrn_standards_decay_% none _diffrn_reflns_number 13482 _diffrn_reflns_av_R_equivalents 0.0572 _diffrn_reflns_av_sigmaI/netI 0.0697 _diffrn_reflns_limit_h_min -29 _diffrn_reflns_limit_h_max 16 _diffrn_reflns_limit_k_min -19 _diffrn_reflns_limit_k_max 18 _diffrn_reflns_limit_l_min -18 _diffrn_reflns_limit_l_max 19 _diffrn_reflns_theta_min 1.67 _diffrn_reflns_theta_max 26.08 _reflns_number_total 4878 _reflns_number_gt 3842 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SMART' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics SHELXP-97 _computing_publication_material SHELXTL _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0371P)^2^+33.6301P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 4878 _refine_ls_number_parameters 289 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0588 _refine_ls_R_factor_gt 0.0445 _refine_ls_wR_factor_ref 0.1087 _refine_ls_wR_factor_gt 0.1010 _refine_ls_goodness_of_fit_ref 1.055 _refine_ls_restrained_S_all 1.055 _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 Dy1 Dy 0.189518(13) 0.328018(18) 0.37646(2) 0.01549(11) Uani 1 1 d . . . C1 C 0.3672(3) 0.5395(4) 0.1735(5) 0.0207(14) Uani 1 1 d . . . C2 C 0.3564(3) 0.4573(4) 0.1373(5) 0.0239(15) Uani 1 1 d . . . H2A H 0.3201 0.4460 0.0696 0.029 Uiso 1 1 calc R . . C3 C 0.3976(3) 0.3911(4) 0.1975(5) 0.0233(15) Uani 1 1 d . . . C4 C 0.4521(3) 0.4069(4) 0.2966(5) 0.0265(16) Uani 1 1 d . . . C5 C 0.4656(3) 0.4900(5) 0.3325(5) 0.0290(16) Uani 1 1 d . . . H5A H 0.5040 0.5019 0.3984 0.035 Uiso 1 1 calc R . . C6 C 0.4230(3) 0.5554(5) 0.2722(5) 0.0292(16) Uani 1 1 d . . . H6A H 0.4317 0.6119 0.2979 0.035 Uiso 1 1 calc R . . C7 C 0.4806(3) 0.3102(4) 0.4265(5) 0.0209(14) Uani 1 1 d . . . C8 C 0.4150(3) 0.3106(4) 0.4043(5) 0.0209(14) Uani 1 1 d . . . H8A H 0.3784 0.3348 0.3432 0.025 Uiso 1 1 calc R . . C9 C 0.4028(3) 0.2753(4) 0.4720(5) 0.0186(13) Uani 1 1 d . . . C10 C 0.4565(3) 0.2406(4) 0.5621(5) 0.0226(14) Uani 1 1 d . . . H10A H 0.4486 0.2183 0.6097 0.027 Uiso 1 1 calc R . . C11 C 0.5223(3) 0.2392(4) 0.5816(5) 0.0180(13) Uani 1 1 d . . . C12 C 0.5338(3) 0.2734(4) 0.5126(5) 0.0207(14) Uani 1 1 d . . . H12A H 0.5782 0.2712 0.5250 0.025 Uiso 1 1 calc R . . C13 C 0.3203(3) 0.6108(4) 0.1093(5) 0.0206(14) Uani 1 1 d . . . C14 C 0.3307(3) 0.2742(4) 0.4447(5) 0.0207(14) Uani 1 1 d . . . C15 C 0.5810(3) 0.2038(4) 0.6799(5) 0.0161(13) Uani 1 1 d . . . N1 N 0.3823(3) 0.3054(4) 0.1552(6) 0.0363(16) Uani 1 1 d . . . O1 O 0.3275(2) 0.6797(3) 0.1544(3) 0.0262(11) Uani 1 1 d . . . O2 O 0.2779(2) 0.5958(3) 0.0179(3) 0.0244(10) Uani 1 1 d . . . O3 O 0.3467(3) 0.2995(4) 0.0630(5) 0.0558(17) Uani 1 1 d . . . O4 O 0.4051(4) 0.2437(4) 0.2112(5) 0.065(2) Uani 1 1 d . . . O5 O 0.2857(2) 0.3126(3) 0.3670(3) 0.0261(11) Uani 1 1 d . . . O6 O 0.3175(2) 0.2342(3) 0.5005(3) 0.0240(10) Uani 1 1 d . . . O7 O 0.5705(2) 0.1790(3) 0.7453(3) 0.0233(10) Uani 1 1 d . . . O8 O 0.6395(2) 0.2010(3) 0.6957(3) 0.0214(10) Uani 1 1 d . . . O9 O 0.4965(2) 0.3439(3) 0.3613(4) 0.0332(13) Uani 1 1 d . . . N2 N 0.2307(4) 0.5806(5) 0.2832(6) 0.0612(11) Uani 1 1 d . . . O10 O 0.1900(3) 0.4566(4) 0.3008(5) 0.0612(11) Uani 1 1 d . . . C16 C 0.2283(5) 0.5145(6) 0.3292(7) 0.0612(11) Uani 1 1 d . A . H16 H 0.2641 0.5123 0.3986 0.080 Uiso 1 1 calc R . . C17 C 0.2962(10) 0.6267(13) 0.3271(14) 0.0612(11) Uani 0.50 1 d P A 1 H17A H 0.3308 0.5878 0.3329 0.092 Uiso 0.50 1 calc PR A 1 H17B H 0.3115 0.6480 0.3939 0.092 Uiso 0.50 1 calc PR A 1 H17C H 0.2897 0.6748 0.2837 0.092 Uiso 0.50 1 calc PR A 1 C17' C 0.2488(11) 0.6744(12) 0.3188(15) 0.0612(11) Uani 0.50 1 d P A 2 H17D H 0.2081 0.7034 0.3073 0.092 Uiso 0.50 1 calc PR A 2 H17E H 0.2643 0.7035 0.2811 0.092 Uiso 0.50 1 calc PR A 2 H17F H 0.2854 0.6757 0.3907 0.092 Uiso 0.50 1 calc PR A 2 C18 C 0.1841(5) 0.5854(6) 0.1773(7) 0.0612(11) Uani 1 1 d . A . H18A H 0.1704 0.5277 0.1495 0.092 Uiso 1 1 calc R . . H18B H 0.2062 0.6141 0.1485 0.092 Uiso 1 1 calc R . . H18C H 0.1435 0.6178 0.1608 0.092 Uiso 1 1 calc R . . N3 N 0.0619(4) 0.5289(4) 0.4131(6) 0.0502(9) Uani 1 1 d . . . O11 O 0.1346(3) 0.4333(4) 0.4171(5) 0.0502(9) Uani 1 1 d . . . C19 C 0.0765(5) 0.4576(5) 0.3865(7) 0.0502(9) Uani 1 1 d . A . H19A H 0.0393 0.4220 0.3400 0.060 Uiso 1 1 calc R . . C20 C -0.0079(4) 0.5544(5) 0.3709(7) 0.0502(9) Uani 1 1 d . . . H20A H -0.0390 0.5089 0.3274 0.075 Uiso 1 1 calc R . . H20B H -0.0179 0.6066 0.3315 0.075 Uiso 1 1 calc R . . H20C H -0.0142 0.5651 0.4253 0.075 Uiso 1 1 calc R . . C21 C 0.1160(4) 0.5885(5) 0.4805(7) 0.0502(9) Uani 1 1 d . . . H21A H 0.1608 0.5637 0.5037 0.075 Uiso 1 1 calc R . . H21B H 0.1138 0.6001 0.5385 0.075 Uiso 1 1 calc R . . H21C H 0.1100 0.6420 0.4447 0.075 Uiso 1 1 calc R . . O1W O 0.2546(9) 0.3414(16) 0.1649(18) 0.054(7) Uani 0.25 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 Dy1 0.01283(16) 0.01622(17) 0.01421(17) -0.00109(12) 0.00563(12) -0.00138(12) C1 0.022(3) 0.021(3) 0.020(3) 0.001(3) 0.013(3) 0.004(3) C2 0.024(3) 0.028(4) 0.023(4) 0.002(3) 0.015(3) -0.002(3) C3 0.030(4) 0.017(3) 0.029(4) 0.002(3) 0.021(3) 0.005(3) C4 0.029(4) 0.028(4) 0.033(4) 0.016(3) 0.023(3) 0.013(3) C5 0.025(4) 0.032(4) 0.022(4) 0.003(3) 0.009(3) -0.001(3) C6 0.030(4) 0.026(4) 0.020(4) 0.005(3) 0.007(3) 0.008(3) C7 0.021(3) 0.018(3) 0.027(4) 0.009(3) 0.015(3) 0.002(3) C8 0.018(3) 0.026(4) 0.019(3) 0.006(3) 0.011(3) 0.007(3) C9 0.017(3) 0.021(3) 0.019(3) -0.003(3) 0.011(3) -0.002(3) C10 0.021(3) 0.025(4) 0.022(4) 0.000(3) 0.013(3) 0.000(3) C11 0.018(3) 0.020(3) 0.011(3) -0.002(3) 0.005(3) -0.001(3) C12 0.012(3) 0.021(3) 0.031(4) 0.003(3) 0.013(3) 0.002(2) C13 0.021(3) 0.019(3) 0.018(4) 0.001(3) 0.009(3) 0.002(3) C14 0.018(3) 0.026(4) 0.023(4) -0.005(3) 0.015(3) -0.005(3) C15 0.015(3) 0.019(3) 0.012(3) -0.001(3) 0.006(3) 0.004(2) N1 0.046(4) 0.024(3) 0.048(5) 0.006(3) 0.032(4) 0.010(3) O1 0.035(3) 0.017(2) 0.020(3) 0.0001(19) 0.011(2) 0.004(2) O2 0.022(2) 0.021(2) 0.019(3) 0.0009(19) 0.005(2) 0.0002(19) O3 0.067(4) 0.037(3) 0.043(4) -0.002(3) 0.019(3) 0.004(3) O4 0.117(6) 0.021(3) 0.059(4) 0.013(3) 0.050(4) 0.015(3) O5 0.015(2) 0.039(3) 0.023(3) 0.004(2) 0.010(2) 0.004(2) O6 0.024(2) 0.027(3) 0.025(3) -0.003(2) 0.017(2) -0.006(2) O7 0.017(2) 0.034(3) 0.015(2) 0.006(2) 0.0064(19) -0.001(2) O8 0.016(2) 0.026(2) 0.020(2) 0.002(2) 0.0088(19) 0.0018(19) O9 0.026(3) 0.045(3) 0.039(3) 0.027(2) 0.025(2) 0.020(2) N2 0.070(3) 0.052(2) 0.047(2) 0.0067(19) 0.024(2) -0.0272(19) O10 0.070(3) 0.052(2) 0.047(2) 0.0067(19) 0.024(2) -0.0272(19) C16 0.070(3) 0.052(2) 0.047(2) 0.0067(19) 0.024(2) -0.0272(19) C17 0.070(3) 0.052(2) 0.047(2) 0.0067(19) 0.024(2) -0.0272(19) C17' 0.070(3) 0.052(2) 0.047(2) 0.0067(19) 0.024(2) -0.0272(19) C18 0.070(3) 0.052(2) 0.047(2) 0.0067(19) 0.024(2) -0.0272(19) N3 0.051(2) 0.041(2) 0.064(2) -0.0046(17) 0.0356(19) 0.0098(16) O11 0.051(2) 0.041(2) 0.064(2) -0.0046(17) 0.0356(19) 0.0098(16) C19 0.051(2) 0.041(2) 0.064(2) -0.0046(17) 0.0356(19) 0.0098(16) C20 0.051(2) 0.041(2) 0.064(2) -0.0046(17) 0.0356(19) 0.0098(16) C21 0.051(2) 0.041(2) 0.064(2) -0.0046(17) 0.0356(19) 0.0098(16) O1W 0.011(9) 0.085(19) 0.049(15) 0.045(13) 0.006(10) 0.002(10) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag Dy1 O6 2.295(4) 7_556 ? Dy1 O10 2.357(6) . ? Dy1 O1 2.364(4) 4_545 ? Dy1 O5 2.367(4) . ? Dy1 O2 2.370(4) 6_566 ? Dy1 O7 2.385(4) 8_455 ? Dy1 O11 2.403(5) . ? Dy1 O8 2.490(4) 8_455 ? Dy1 C15 2.776(6) 8_455 ? C1 C2 1.378(9) . ? C1 C6 1.404(9) . ? C1 C13 1.501(9) . ? C2 C3 1.379(9) . ? C3 C4 1.397(10) . ? C3 N1 1.456(9) . ? C4 C5 1.387(10) . ? C4 O9 1.390(8) . ? C5 C6 1.380(9) . ? C7 C12 1.369(9) . ? C7 C8 1.377(8) . ? C7 O9 1.401(8) . ? C8 C9 1.386(9) . ? C9 C10 1.392(9) . ? C9 C14 1.499(8) . ? C10 C11 1.399(8) . ? C11 C12 1.390(9) . ? C11 C15 1.504(8) . ? C13 O2 1.251(7) . ? C13 O1 1.258(7) . ? C14 O5 1.249(8) . ? C14 O6 1.267(8) . ? C15 O8 1.256(7) . ? C15 O7 1.269(8) . ? C15 Dy1 2.776(6) 8_556 ? N1 O4 1.221(8) . ? N1 O3 1.231(9) . ? O1 Dy1 2.364(4) 4 ? O2 Dy1 2.370(4) 6_565 ? O6 Dy1 2.295(4) 7_556 ? O7 Dy1 2.385(4) 8_556 ? O8 Dy1 2.490(4) 8_556 ? N2 C16 1.292(10) . ? N2 C18 1.418(11) . ? N2 C17 1.475(18) . ? N2 C17' 1.548(19) . ? O10 C16 1.178(9) . ? N3 C19 1.309(10) . ? N3 C20 1.439(10) . ? N3 C21 1.459(11) . ? O11 C19 1.228(9) . ? 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 O6 Dy1 O10 146.3(2) 7_556 . ? O6 Dy1 O1 71.18(16) 7_556 4_545 ? O10 Dy1 O1 141.4(2) . 4_545 ? O6 Dy1 O5 123.18(16) 7_556 . ? O10 Dy1 O5 76.8(2) . . ? O1 Dy1 O5 86.63(16) 4_545 . ? O6 Dy1 O2 80.58(16) 7_556 6_566 ? O10 Dy1 O2 78.96(18) . 6_566 ? O1 Dy1 O2 130.62(15) 4_545 6_566 ? O5 Dy1 O2 75.89(16) . 6_566 ? O6 Dy1 O7 97.11(16) 7_556 8_455 ? O10 Dy1 O7 85.83(18) . 8_455 ? O1 Dy1 O7 78.02(15) 4_545 8_455 ? O5 Dy1 O7 129.22(16) . 8_455 ? O2 Dy1 O7 146.65(15) 6_566 8_455 ? O6 Dy1 O11 75.33(19) 7_556 . ? O10 Dy1 O11 73.3(2) . . ? O1 Dy1 O11 132.77(18) 4_545 . ? O5 Dy1 O11 140.23(18) . . ? O2 Dy1 O11 73.15(18) 6_566 . ? O7 Dy1 O11 74.10(18) 8_455 . ? O6 Dy1 O8 135.49(15) 7_556 8_455 ? O10 Dy1 O8 71.94(19) . 8_455 ? O1 Dy1 O8 70.22(15) 4_545 8_455 ? O5 Dy1 O8 75.49(15) . 8_455 ? O2 Dy1 O8 142.91(15) 6_566 8_455 ? O7 Dy1 O8 53.74(14) 8_455 8_455 ? O11 Dy1 O8 117.94(18) . 8_455 ? O6 Dy1 C15 116.02(16) 7_556 8_455 ? O10 Dy1 C15 80.48(19) . 8_455 ? O1 Dy1 C15 69.19(17) 4_545 8_455 ? O5 Dy1 C15 102.27(17) . 8_455 ? O2 Dy1 C15 159.22(17) 6_566 8_455 ? O7 Dy1 C15 27.14(16) 8_455 8_455 ? O11 Dy1 C15 98.0(2) . 8_455 ? O8 Dy1 C15 26.91(15) 8_455 8_455 ? C2 C1 C6 118.5(6) . . ? C2 C1 C13 121.1(6) . . ? C6 C1 C13 120.4(6) . . ? C1 C2 C3 121.1(6) . . ? C2 C3 C4 120.1(6) . . ? C2 C3 N1 118.3(6) . . ? C4 C3 N1 121.6(6) . . ? C5 C4 O9 117.1(7) . . ? C5 C4 C3 119.3(6) . . ? O9 C4 C3 123.5(6) . . ? C6 C5 C4 120.0(7) . . ? C5 C6 C1 120.8(7) . . ? C12 C7 C8 121.5(6) . . ? C12 C7 O9 115.9(5) . . ? C8 C7 O9 122.5(6) . . ? C7 C8 C9 119.4(6) . . ? C8 C9 C10 120.4(6) . . ? C8 C9 C14 118.4(6) . . ? C10 C9 C14 121.2(6) . . ? C9 C10 C11 119.0(6) . . ? C12 C11 C10 120.2(6) . . ? C12 C11 C15 120.3(5) . . ? C10 C11 C15 119.4(6) . . ? C7 C12 C11 119.4(6) . . ? O2 C13 O1 126.7(6) . . ? O2 C13 C1 117.5(6) . . ? O1 C13 C1 115.7(6) . . ? O5 C14 O6 122.6(6) . . ? O5 C14 C9 118.3(6) . . ? O6 C14 C9 119.1(6) . . ? O8 C15 O7 121.7(5) . . ? O8 C15 C11 118.8(6) . . ? O7 C15 C11 119.5(5) . . ? O8 C15 Dy1 63.8(3) . 8_556 ? O7 C15 Dy1 59.0(3) . 8_556 ? C11 C15 Dy1 168.1(4) . 8_556 ? O4 N1 O3 123.3(7) . . ? O4 N1 C3 119.7(7) . . ? O3 N1 C3 117.1(6) . . ? C13 O1 Dy1 140.4(4) . 4 ? C13 O2 Dy1 136.5(4) . 6_565 ? C14 O5 Dy1 107.0(4) . . ? C14 O6 Dy1 170.4(4) . 7_556 ? C15 O7 Dy1 93.8(3) . 8_556 ? C15 O8 Dy1 89.3(4) . 8_556 ? C4 O9 C7 115.0(5) . . ? C16 N2 C18 118.4(8) . . ? C16 N2 C17 119.2(10) . . ? C18 N2 C17 116.5(9) . . ? C16 N2 C17' 129.8(11) . . ? C18 N2 C17' 105.1(10) . . ? C17 N2 C17' 50.3(11) . . ? C16 O10 Dy1 133.2(6) . . ? O10 C16 N2 131.9(10) . . ? C19 N3 C20 121.6(8) . . ? C19 N3 C21 120.6(7) . . ? C20 N3 C21 117.6(7) . . ? C19 O11 Dy1 139.0(6) . . ? O11 C19 N3 124.9(9) . . ? _diffrn_measured_fraction_theta_max 0.997 _diffrn_reflns_theta_full 26.08 _diffrn_measured_fraction_theta_full 0.997 _refine_diff_density_max 2.778 _refine_diff_density_min -2.201 _refine_diff_density_rms 0.170 data_10 _database_code_depnum_ccdc_archive 'CCDC 857011' #TrackingRef '- 1-12 and 7.CIF' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point 'not measured' _chemical_formula_moiety 'C21 H20.50 Ho N3 O11.25' _chemical_formula_sum 'C21 H20.50 Ho N3 O11.25' _chemical_formula_weight 659.83 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' 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 C2/c loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y, -z+1/2' 'x+1/2, y+1/2, z' '-x+1/2, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y, z-1/2' '-x+1/2, -y+1/2, -z' 'x+1/2, -y+1/2, z-1/2' _cell_length_a 23.5634(10) _cell_length_b 15.6940(7) _cell_length_c 16.0403(7) _cell_angle_alpha 90.00 _cell_angle_beta 124.0830(10) _cell_angle_gamma 90.00 _cell_volume 4912.8(4) _cell_formula_units_Z 8 _cell_measurement_temperature 185(2) _cell_measurement_reflns_used 4851 _cell_measurement_theta_min 1.82 _cell_measurement_theta_max 26.03 _exptl_crystal_description rod _exptl_crystal_colour 'light yellow' _exptl_crystal_size_max 0.22 _exptl_crystal_size_mid 0.17 _exptl_crystal_size_min 0.14 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.784 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 2596 _exptl_absorpt_coefficient_mu 3.286 _exptl_absorpt_correction_type empirical _exptl_absorpt_correction_T_min 0.5318 _exptl_absorpt_correction_T_max 0.6562 _exptl_absorpt_process_details SADABS _exptl_special_details ; ? ; _diffrn_ambient_temperature 185(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'CCD area detector' _diffrn_measurement_method 'phi and omega scans' _diffrn_detector_area_resol_mean 9.00cm _diffrn_standards_number none _diffrn_standards_interval_count none _diffrn_standards_interval_time none _diffrn_standards_decay_% none _diffrn_reflns_number 13390 _diffrn_reflns_av_R_equivalents 0.0306 _diffrn_reflns_av_sigmaI/netI 0.0364 _diffrn_reflns_limit_h_min -29 _diffrn_reflns_limit_h_max 14 _diffrn_reflns_limit_k_min -19 _diffrn_reflns_limit_k_max 19 _diffrn_reflns_limit_l_min -12 _diffrn_reflns_limit_l_max 19 _diffrn_reflns_theta_min 1.82 _diffrn_reflns_theta_max 26.03 _reflns_number_total 4851 _reflns_number_gt 4191 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SMART' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics SHELXP-97 _computing_publication_material SHELXTL _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0371P)^2^+47.2882P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 4851 _refine_ls_number_parameters 289 _refine_ls_number_restraints 6 _refine_ls_R_factor_all 0.0425 _refine_ls_R_factor_gt 0.0356 _refine_ls_wR_factor_ref 0.0876 _refine_ls_wR_factor_gt 0.0839 _refine_ls_goodness_of_fit_ref 1.037 _refine_ls_restrained_S_all 1.038 _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 Ho1 Ho 0.189189(10) 0.672319(13) 0.375649(15) 0.01470(8) Uani 1 1 d . . . C1 C 0.3670(3) 0.4603(3) 0.1727(4) 0.0225(11) Uani 1 1 d . . . C2 C 0.3555(3) 0.5423(3) 0.1354(4) 0.0235(11) Uani 1 1 d . . . H2A H 0.3190 0.5534 0.0677 0.028 Uiso 1 1 calc R . . C3 C 0.3972(3) 0.6085(3) 0.1965(4) 0.0230(11) Uani 1 1 d . . . C4 C 0.4515(3) 0.5930(4) 0.2957(4) 0.0239(11) Uani 1 1 d . . . C5 C 0.4645(3) 0.5100(4) 0.3310(4) 0.0299(13) Uani 1 1 d . . . H5A H 0.5027 0.4982 0.3973 0.036 Uiso 1 1 calc R . . C6 C 0.4223(3) 0.4438(4) 0.2707(4) 0.0300(13) Uani 1 1 d . . . H6A H 0.4311 0.3872 0.2962 0.036 Uiso 1 1 calc R . . C7 C 0.4800(3) 0.6903(3) 0.4250(4) 0.0215(11) Uani 1 1 d . . . C8 C 0.4144(3) 0.6896(3) 0.4038(4) 0.0211(11) Uani 1 1 d . . . H8A H 0.3777 0.6649 0.3431 0.025 Uiso 1 1 calc R . . C9 C 0.4028(2) 0.7253(3) 0.4715(4) 0.0192(10) Uani 1 1 d . . . C10 C 0.4570(3) 0.7591(3) 0.5622(4) 0.0193(10) Uani 1 1 d . . . H10A H 0.4494 0.7809 0.6104 0.023 Uiso 1 1 calc R . . C11 C 0.5225(2) 0.7608(3) 0.5814(4) 0.0177(10) Uani 1 1 d . . . C12 C 0.5342(2) 0.7267(3) 0.5120(4) 0.0189(10) Uani 1 1 d . . . H12A H 0.5786 0.7285 0.5243 0.023 Uiso 1 1 calc R . . C13 C 0.3192(2) 0.3881(3) 0.1082(4) 0.0206(11) Uani 1 1 d . . . C14 C 0.3310(2) 0.7268(3) 0.4458(4) 0.0192(10) Uani 1 1 d . . . C15 C 0.5817(2) 0.7958(3) 0.6798(4) 0.0182(10) Uani 1 1 d . . . C16 C 0.2290(4) 0.4876(5) 0.3280(6) 0.0587(9) Uani 1 1 d . A . H16 H 0.2652 0.4903 0.3973 0.088 Uiso 1 1 calc R . . C18 C 0.1832(4) 0.4163(5) 0.1756(5) 0.0587(9) Uani 1 1 d . A . H18A H 0.1421 0.4496 0.1554 0.088 Uiso 1 1 calc R . . H18B H 0.1704 0.3567 0.1561 0.088 Uiso 1 1 calc R . . H18C H 0.2042 0.4392 0.1422 0.088 Uiso 1 1 calc R . . C19 C 0.0763(4) 0.5432(5) 0.3854(6) 0.0503(7) Uani 1 1 d . A . H19A H 0.0393 0.5796 0.3403 0.060 Uiso 1 1 calc R . . C20 C 0.1159(4) 0.4116(5) 0.4790(6) 0.0503(7) Uani 1 1 d . . . H20A H 0.1605 0.4356 0.5004 0.075 Uiso 1 1 calc R . . H20B H 0.1090 0.3576 0.4437 0.075 Uiso 1 1 calc R . . H20C H 0.1147 0.4014 0.5382 0.075 Uiso 1 1 calc R . . C21 C -0.0086(4) 0.4478(5) 0.3709(6) 0.0503(7) Uani 1 1 d . . . H21A H -0.0393 0.4935 0.3273 0.075 Uiso 1 1 calc R . . H21B H -0.0143 0.4386 0.4263 0.075 Uiso 1 1 calc R . . H21C H -0.0198 0.3951 0.3318 0.075 Uiso 1 1 calc R . . N1 N 0.3816(3) 0.6936(3) 0.1534(4) 0.0341(12) Uani 1 1 d . . . N2 N 0.2306(3) 0.4216(4) 0.2817(4) 0.0587(9) Uani 1 1 d . . . N3 N 0.0617(3) 0.4714(4) 0.4115(5) 0.0503(7) Uani 1 1 d . . . O1 O 0.3264(2) 0.3197(2) 0.1537(3) 0.0261(8) Uani 1 1 d . . . O2 O 0.27684(17) 0.4031(2) 0.0164(2) 0.0215(8) Uani 1 1 d . . . O3 O 0.3466(3) 0.7001(3) 0.0609(4) 0.0521(13) Uani 1 1 d . . . O4 O 0.4037(3) 0.7551(3) 0.2096(4) 0.0621(16) Uani 1 1 d . . . O5 O 0.28506(17) 0.6889(2) 0.3676(3) 0.0240(8) Uani 1 1 d . . . O6 O 0.31847(18) 0.7665(2) 0.5018(3) 0.0245(8) Uani 1 1 d . . . O7 O 0.57080(18) 0.8201(2) 0.7450(3) 0.0229(8) Uani 1 1 d . . . O8 O 0.63985(17) 0.7983(2) 0.6956(3) 0.0210(7) Uani 1 1 d . . . O9 O 0.4956(2) 0.6557(3) 0.3596(3) 0.0331(10) Uani 1 1 d . . . O10 O 0.1903(3) 0.5452(3) 0.2994(4) 0.0587(9) Uani 1 1 d . . . O11 O 0.1348(3) 0.5667(3) 0.4155(4) 0.0503(7) Uani 1 1 d . . . O1W O 0.2547(9) 0.6590(12) 0.1643(13) 0.043(4) Uani 0.25 1 d PU . . C17 C 0.2981(9) 0.3745(10) 0.3285(11) 0.0587(9) Uani 0.50 1 d P A 1 H17A H 0.3332 0.4137 0.3365 0.088 Uiso 0.50 1 calc PR A 1 H17B H 0.2926 0.3272 0.2846 0.088 Uiso 0.50 1 calc PR A 1 H17C H 0.3121 0.3523 0.3945 0.088 Uiso 0.50 1 calc PR A 1 C17' C 0.2526(9) 0.3307(10) 0.3168(11) 0.0587(9) Uani 0.50 1 d P A 2 H17D H 0.2133 0.2980 0.3050 0.088 Uiso 0.50 1 calc PR A 2 H17E H 0.2889 0.3304 0.3889 0.088 Uiso 0.50 1 calc PR A 2 H17F H 0.2697 0.3049 0.2793 0.088 Uiso 0.50 1 calc PR A 2 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 Ho1 0.01320(12) 0.01522(13) 0.01251(12) 0.00097(9) 0.00526(9) 0.00125(9) C1 0.023(3) 0.025(3) 0.019(3) -0.002(2) 0.011(2) -0.002(2) C2 0.022(3) 0.027(3) 0.019(3) -0.002(2) 0.010(2) -0.001(2) C3 0.027(3) 0.021(3) 0.026(3) -0.006(2) 0.018(2) -0.003(2) C4 0.022(3) 0.031(3) 0.024(3) -0.013(2) 0.017(2) -0.011(2) C5 0.025(3) 0.034(3) 0.020(3) -0.003(2) 0.006(2) -0.001(2) C6 0.033(3) 0.026(3) 0.020(3) -0.003(2) 0.008(2) -0.004(2) C7 0.026(3) 0.023(3) 0.023(3) -0.009(2) 0.017(2) -0.005(2) C8 0.019(2) 0.025(3) 0.016(2) -0.007(2) 0.008(2) -0.007(2) C9 0.019(2) 0.020(3) 0.019(2) 0.000(2) 0.011(2) 0.002(2) C10 0.022(3) 0.022(3) 0.014(2) -0.0009(19) 0.010(2) 0.002(2) C11 0.017(2) 0.017(2) 0.015(2) 0.0006(19) 0.007(2) -0.0016(19) C12 0.017(2) 0.020(3) 0.021(3) -0.003(2) 0.012(2) -0.002(2) C13 0.019(2) 0.021(3) 0.018(3) -0.005(2) 0.008(2) -0.003(2) C14 0.019(2) 0.022(3) 0.017(2) 0.006(2) 0.010(2) 0.003(2) C15 0.020(2) 0.017(2) 0.016(2) 0.0006(19) 0.008(2) 0.001(2) C16 0.070(2) 0.0476(18) 0.0425(16) -0.0060(14) 0.0219(16) 0.0266(15) C18 0.070(2) 0.0476(18) 0.0425(16) -0.0060(14) 0.0219(16) 0.0266(15) C19 0.0521(17) 0.0434(16) 0.0584(18) 0.0054(13) 0.0328(15) -0.0121(13) C20 0.0521(17) 0.0434(16) 0.0584(18) 0.0054(13) 0.0328(15) -0.0121(13) C21 0.0521(17) 0.0434(16) 0.0584(18) 0.0054(13) 0.0328(15) -0.0121(13) N1 0.043(3) 0.026(3) 0.040(3) -0.008(2) 0.027(3) -0.008(2) N2 0.070(2) 0.0476(18) 0.0425(16) -0.0060(14) 0.0219(16) 0.0266(15) N3 0.0521(17) 0.0434(16) 0.0584(18) 0.0054(13) 0.0328(15) -0.0121(13) O1 0.033(2) 0.0181(19) 0.0192(18) -0.0003(15) 0.0100(16) -0.0021(16) O2 0.0219(18) 0.0186(18) 0.0151(17) -0.0021(14) 0.0049(15) -0.0036(14) O3 0.062(3) 0.037(3) 0.039(3) 0.005(2) 0.017(2) -0.003(2) O4 0.107(5) 0.023(2) 0.056(3) -0.015(2) 0.046(3) -0.014(3) O5 0.0142(17) 0.035(2) 0.0179(18) -0.0018(15) 0.0062(15) -0.0034(15) O6 0.025(2) 0.028(2) 0.0258(19) 0.0025(16) 0.0173(17) 0.0054(16) O7 0.0178(18) 0.032(2) 0.0165(18) -0.0081(15) 0.0084(15) -0.0006(15) O8 0.0159(17) 0.0269(19) 0.0183(18) -0.0019(15) 0.0084(15) -0.0018(15) O9 0.027(2) 0.045(3) 0.039(2) -0.0262(19) 0.0249(19) -0.0214(18) O10 0.070(2) 0.0476(18) 0.0425(16) -0.0060(14) 0.0219(16) 0.0266(15) O11 0.0521(17) 0.0434(16) 0.0584(18) 0.0054(13) 0.0328(15) -0.0121(13) O1W 0.036(7) 0.064(9) 0.037(7) -0.021(6) 0.026(6) 0.003(6) C17 0.070(2) 0.0476(18) 0.0425(16) -0.0060(14) 0.0219(16) 0.0266(15) C17' 0.070(2) 0.0476(18) 0.0425(16) -0.0060(14) 0.0219(16) 0.0266(15) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag Ho1 O6 2.284(4) 7_566 ? Ho1 O1 2.347(3) 4 ? Ho1 O5 2.348(4) . ? Ho1 O10 2.348(5) . ? Ho1 O2 2.353(3) 6_566 ? Ho1 O7 2.374(3) 8_465 ? Ho1 O11 2.392(4) . ? Ho1 O8 2.478(3) 8_465 ? Ho1 C15 2.760(5) 8_465 ? Ho1 C14 2.992(5) . ? C1 C2 1.381(7) . ? C1 C6 1.393(7) . ? C1 C13 1.522(7) . ? C2 C3 1.388(7) . ? C3 C4 1.396(8) . ? C3 N1 1.453(7) . ? C4 O9 1.381(6) . ? C4 C5 1.385(8) . ? C5 C6 1.388(8) . ? C7 C12 1.381(7) . ? C7 C8 1.384(7) . ? C7 O9 1.401(6) . ? C8 C9 1.380(7) . ? C9 C10 1.395(7) . ? C9 C14 1.500(7) . ? C10 C11 1.395(7) . ? C11 C12 1.394(7) . ? C11 C15 1.507(7) . ? C13 O2 1.255(6) . ? C13 O1 1.256(6) . ? C14 O5 1.256(6) . ? C14 O6 1.257(6) . ? C15 O8 1.247(6) . ? C15 O7 1.267(6) . ? C15 Ho1 2.760(5) 8_566 ? C16 O10 1.178(8) . ? C16 N2 1.287(9) . ? C18 N2 1.422(9) . ? C19 O11 1.234(8) . ? C19 N3 1.314(8) . ? C20 N3 1.462(9) . ? C21 N3 1.448(9) . ? N1 O4 1.220(6) . ? N1 O3 1.233(7) . ? N2 C17' 1.515(15) . ? N2 C17 1.517(15) . ? O1 Ho1 2.347(3) 4_545 ? O2 Ho1 2.353(3) 6_565 ? O6 Ho1 2.284(4) 7_566 ? O7 Ho1 2.374(3) 8_566 ? O8 Ho1 2.478(3) 8_566 ? 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 O6 Ho1 O1 71.31(13) 7_566 4 ? O6 Ho1 O5 122.90(13) 7_566 . ? O1 Ho1 O5 85.84(13) 4 . ? O6 Ho1 O10 146.59(17) 7_566 . ? O1 Ho1 O10 141.15(16) 4 . ? O5 Ho1 O10 76.92(17) . . ? O6 Ho1 O2 80.57(12) 7_566 6_566 ? O1 Ho1 O2 130.00(12) 4 6_566 ? O5 Ho1 O2 75.75(13) . 6_566 ? O10 Ho1 O2 79.16(14) . 6_566 ? O6 Ho1 O7 96.79(13) 7_566 8_465 ? O1 Ho1 O7 78.41(13) 4 8_465 ? O5 Ho1 O7 129.56(12) . 8_465 ? O10 Ho1 O7 86.17(16) . 8_465 ? O2 Ho1 O7 146.87(12) 6_566 8_465 ? O6 Ho1 O11 75.42(16) 7_566 . ? O1 Ho1 O11 133.57(16) 4 . ? O5 Ho1 O11 140.15(16) . . ? O10 Ho1 O11 73.41(19) . . ? O2 Ho1 O11 73.06(15) 6_566 . ? O7 Ho1 O11 74.33(15) 8_465 . ? O6 Ho1 O8 135.48(12) 7_566 8_465 ? O1 Ho1 O8 70.38(12) 4 8_465 ? O5 Ho1 O8 75.71(12) . 8_465 ? O10 Ho1 O8 71.71(15) . 8_465 ? O2 Ho1 O8 142.92(12) 6_566 8_465 ? O7 Ho1 O8 53.85(11) 8_465 8_465 ? O11 Ho1 O8 117.97(15) . 8_465 ? O6 Ho1 C15 116.01(14) 7_566 8_465 ? O1 Ho1 C15 69.65(14) 4 8_465 ? O5 Ho1 C15 102.44(13) . 8_465 ? O10 Ho1 C15 80.35(16) . 8_465 ? O2 Ho1 C15 159.29(13) 6_566 8_465 ? O7 Ho1 C15 27.26(13) 8_465 8_465 ? O11 Ho1 C15 98.18(16) . 8_465 ? O8 Ho1 C15 26.86(13) 8_465 8_465 ? O6 Ho1 C14 99.58(13) 7_566 . ? O1 Ho1 C14 79.06(14) 4 . ? O5 Ho1 C14 23.47(13) . . ? O10 Ho1 C14 95.90(18) . . ? O2 Ho1 C14 65.68(13) 6_566 . ? O7 Ho1 C14 146.10(12) 8_465 . ? O11 Ho1 C14 138.66(15) . . ? O8 Ho1 C14 94.63(12) 8_465 . ? C15 Ho1 C14 119.71(14) 8_465 . ? C2 C1 C6 119.6(5) . . ? C2 C1 C13 120.6(5) . . ? C6 C1 C13 119.8(5) . . ? C1 C2 C3 120.2(5) . . ? C2 C3 C4 120.5(5) . . ? C2 C3 N1 117.6(5) . . ? C4 C3 N1 121.9(5) . . ? O9 C4 C5 117.7(5) . . ? O9 C4 C3 123.4(5) . . ? C5 C4 C3 118.8(5) . . ? C4 C5 C6 120.8(5) . . ? C5 C6 C1 119.9(5) . . ? C12 C7 C8 121.7(5) . . ? C12 C7 O9 115.8(4) . . ? C8 C7 O9 122.6(4) . . ? C9 C8 C7 119.3(5) . . ? C8 C9 C10 120.4(5) . . ? C8 C9 C14 118.7(4) . . ? C10 C9 C14 120.9(5) . . ? C9 C10 C11 119.4(5) . . ? C12 C11 C10 120.4(4) . . ? C12 C11 C15 119.7(4) . . ? C10 C11 C15 119.8(4) . . ? C7 C12 C11 118.8(5) . . ? O2 C13 O1 127.1(5) . . ? O2 C13 C1 117.2(5) . . ? O1 C13 C1 115.7(4) . . ? O5 C14 O6 122.1(5) . . ? O5 C14 C9 118.4(4) . . ? O6 C14 C9 119.4(4) . . ? O5 C14 Ho1 48.1(2) . . ? O6 C14 Ho1 75.5(3) . . ? C9 C14 Ho1 161.6(4) . . ? O8 C15 O7 122.0(4) . . ? O8 C15 C11 119.4(4) . . ? O7 C15 C11 118.6(4) . . ? O8 C15 Ho1 63.9(3) . 8_566 ? O7 C15 Ho1 59.1(2) . 8_566 ? C11 C15 Ho1 168.1(3) . 8_566 ? O10 C16 N2 131.2(7) . . ? O11 C19 N3 124.4(7) . . ? O4 N1 O3 123.0(6) . . ? O4 N1 C3 119.1(5) . . ? O3 N1 C3 117.9(5) . . ? C16 N2 C18 118.7(6) . . ? C16 N2 C17' 131.1(8) . . ? C18 N2 C17' 105.4(8) . . ? C16 N2 C17 118.0(8) . . ? C18 N2 C17 117.8(7) . . ? C17' N2 C17 46.5(9) . . ? C19 N3 C21 120.9(6) . . ? C19 N3 C20 120.7(6) . . ? C21 N3 C20 118.3(6) . . ? C13 O1 Ho1 140.4(3) . 4_545 ? C13 O2 Ho1 136.4(3) . 6_565 ? C14 O5 Ho1 108.4(3) . . ? C14 O6 Ho1 170.8(3) . 7_566 ? C15 O7 Ho1 93.6(3) . 8_566 ? C15 O8 Ho1 89.3(3) . 8_566 ? C4 O9 C7 115.3(4) . . ? C16 O10 Ho1 132.9(5) . . ? C19 O11 Ho1 138.6(5) . . ? _diffrn_measured_fraction_theta_max 0.998 _diffrn_reflns_theta_full 26.03 _diffrn_measured_fraction_theta_full 0.998 _refine_diff_density_max 2.809 _refine_diff_density_min -2.622 _refine_diff_density_rms 0.138 data_11 _database_code_depnum_ccdc_archive 'CCDC 857012' #TrackingRef '- 1-12 and 7.CIF' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point 'not measured' _chemical_formula_moiety 'C21 H20.50 Er N3 O11.25' _chemical_formula_sum 'C21 H20.50 Er N3 O11.25' _chemical_formula_weight 662.16 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' 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 C2/c loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y, -z+1/2' 'x+1/2, y+1/2, z' '-x+1/2, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y, z-1/2' '-x+1/2, -y+1/2, -z' 'x+1/2, -y+1/2, z-1/2' _cell_length_a 23.483(4) _cell_length_b 15.623(3) _cell_length_c 15.964(3) _cell_angle_alpha 90.00 _cell_angle_beta 124.008(2) _cell_angle_gamma 90.00 _cell_volume 4854.9(16) _cell_formula_units_Z 8 _cell_measurement_temperature 185(2) _cell_measurement_reflns_used 4830 _cell_measurement_theta_min 1.67 _cell_measurement_theta_max 26.18 _exptl_crystal_description rod _exptl_crystal_colour 'light yellow' _exptl_crystal_size_max 0.15 _exptl_crystal_size_mid 0.12 _exptl_crystal_size_min 0.11 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.812 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 2604 _exptl_absorpt_coefficient_mu 3.523 _exptl_absorpt_correction_type empirical _exptl_absorpt_correction_T_min 0.6201 _exptl_absorpt_correction_T_max 0.6979 _exptl_absorpt_process_details SADABS _exptl_special_details ; ? ; _diffrn_ambient_temperature 185(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'CCD area detector' _diffrn_measurement_method 'phi and omega scans' _diffrn_detector_area_resol_mean 9.00cm _diffrn_standards_number none _diffrn_standards_interval_count none _diffrn_standards_interval_time none _diffrn_standards_decay_% none _diffrn_reflns_number 13377 _diffrn_reflns_av_R_equivalents 0.0613 _diffrn_reflns_av_sigmaI/netI 0.0738 _diffrn_reflns_limit_h_min -29 _diffrn_reflns_limit_h_max 16 _diffrn_reflns_limit_k_min -19 _diffrn_reflns_limit_k_max 17 _diffrn_reflns_limit_l_min -18 _diffrn_reflns_limit_l_max 19 _diffrn_reflns_theta_min 1.67 _diffrn_reflns_theta_max 26.18 _reflns_number_total 4830 _reflns_number_gt 3784 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SMART' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics SHELXP-97 _computing_publication_material SHELXTL _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0418P)^2^+36.1369P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 4830 _refine_ls_number_parameters 289 _refine_ls_number_restraints 6 _refine_ls_R_factor_all 0.0610 _refine_ls_R_factor_gt 0.0451 _refine_ls_wR_factor_ref 0.1109 _refine_ls_wR_factor_gt 0.1020 _refine_ls_goodness_of_fit_ref 1.024 _refine_ls_restrained_S_all 1.023 _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 Er1 Er 0.189212(14) 0.671958(19) 0.37499(2) 0.01420(11) Uani 1 1 d . . . C1 C 0.3659(3) 0.4586(5) 0.1717(5) 0.0222(16) Uani 1 1 d . . . C2 C 0.3554(4) 0.5419(5) 0.1360(5) 0.0261(17) Uani 1 1 d . . . H2A H 0.3188 0.5536 0.0682 0.031 Uiso 1 1 calc R . . C3 C 0.3967(4) 0.6079(5) 0.1962(5) 0.0226(16) Uani 1 1 d . . . C4 C 0.4512(4) 0.5916(5) 0.2959(5) 0.0240(17) Uani 1 1 d . . . C5 C 0.4634(4) 0.5082(5) 0.3302(6) 0.0313(18) Uani 1 1 d . . . H5A H 0.5016 0.4962 0.3967 0.038 Uiso 1 1 calc R . . C6 C 0.4214(4) 0.4419(5) 0.2703(5) 0.0293(18) Uani 1 1 d . . . H6A H 0.4303 0.3852 0.2960 0.035 Uiso 1 1 calc R . . C7 C 0.4806(3) 0.6896(4) 0.4254(5) 0.0175(15) Uani 1 1 d . . . C8 C 0.4153(3) 0.6894(5) 0.4044(5) 0.0194(15) Uani 1 1 d . . . H8A H 0.3785 0.6646 0.3435 0.023 Uiso 1 1 calc R . . C9 C 0.4034(3) 0.7258(4) 0.4731(5) 0.0174(14) Uani 1 1 d . . . C10 C 0.4574(3) 0.7589(5) 0.5625(5) 0.0193(15) Uani 1 1 d . . . H10A H 0.4501 0.7808 0.6112 0.023 Uiso 1 1 calc R . . C11 C 0.5227(3) 0.7601(4) 0.5814(5) 0.0162(14) Uani 1 1 d . . . C12 C 0.5347(3) 0.7255(4) 0.5128(5) 0.0182(15) Uani 1 1 d . . . H12A H 0.5794 0.7264 0.5258 0.022 Uiso 1 1 calc R . . C13 C 0.3183(3) 0.3873(5) 0.1080(5) 0.0206(15) Uani 1 1 d . . . C14 C 0.3318(4) 0.7285(5) 0.4474(5) 0.0202(15) Uani 1 1 d . . . C15 C 0.5816(3) 0.7957(4) 0.6792(5) 0.0154(14) Uani 1 1 d . . . C16 C 0.2291(5) 0.4899(7) 0.3266(7) 0.0560(11) Uani 1 1 d . A . H16 H 0.2666 0.4943 0.3953 0.084 Uiso 1 1 calc R . . C17 C 0.2969(11) 0.3732(14) 0.3286(14) 0.0560(11) Uani 0.50 1 d P A 1 H17A H 0.3332 0.4120 0.3392 0.084 Uiso 0.50 1 calc PR A 1 H17B H 0.2913 0.3266 0.2834 0.084 Uiso 0.50 1 calc PR A 1 H17C H 0.3095 0.3493 0.3936 0.084 Uiso 0.50 1 calc PR A 1 C17' C 0.2514(12) 0.3298(13) 0.3154(15) 0.0560(11) Uani 0.50 1 d P A 2 H17D H 0.2113 0.2971 0.3013 0.084 Uiso 0.50 1 calc PR A 2 H17E H 0.2869 0.3284 0.3881 0.084 Uiso 0.50 1 calc PR A 2 H17F H 0.2694 0.3045 0.2785 0.084 Uiso 0.50 1 calc PR A 2 C18 C 0.1831(5) 0.4179(6) 0.1751(7) 0.0560(11) Uani 1 1 d . A . H18A H 0.1416 0.4502 0.1552 0.084 Uiso 1 1 calc R . . H18B H 0.1709 0.3580 0.1541 0.084 Uiso 1 1 calc R . . H18C H 0.2043 0.4426 0.1423 0.084 Uiso 1 1 calc R . . C19 C 0.0768(5) 0.5432(6) 0.3849(7) 0.0477(9) Uani 1 1 d . A . H19A H 0.0403 0.5811 0.3413 0.057 Uiso 1 1 calc R . . C20 C 0.1152(5) 0.4110(6) 0.4757(7) 0.0477(9) Uani 1 1 d . . . H20A H 0.1597 0.4357 0.4969 0.072 Uiso 1 1 calc R . . H20B H 0.1082 0.3575 0.4390 0.072 Uiso 1 1 calc R . . H20C H 0.1144 0.3993 0.5353 0.072 Uiso 1 1 calc R . . C21 C -0.0083(5) 0.4471(6) 0.3706(7) 0.0477(9) Uani 1 1 d . . . H21A H -0.0387 0.4943 0.3293 0.072 Uiso 1 1 calc R . . H21B H -0.0137 0.4356 0.4262 0.072 Uiso 1 1 calc R . . H21C H -0.0203 0.3957 0.3287 0.072 Uiso 1 1 calc R . . N1 N 0.3819(4) 0.6930(4) 0.1546(5) 0.0351(17) Uani 1 1 d . . . N2 N 0.2304(4) 0.4219(5) 0.2817(6) 0.0560(11) Uani 1 1 d . . . N3 N 0.0615(4) 0.4702(5) 0.4110(6) 0.0477(9) Uani 1 1 d . . . O1 O 0.3254(3) 0.3188(3) 0.1530(4) 0.0231(11) Uani 1 1 d . . . O2 O 0.2765(2) 0.4025(3) 0.0156(3) 0.0210(11) Uani 1 1 d . . . O3 O 0.3464(4) 0.6991(4) 0.0616(5) 0.0515(17) Uani 1 1 d . . . O4 O 0.4041(4) 0.7543(4) 0.2099(5) 0.062(2) Uani 1 1 d . . . O5 O 0.2852(2) 0.6905(3) 0.3695(3) 0.0223(11) Uani 1 1 d . . . O6 O 0.3201(2) 0.7681(3) 0.5044(3) 0.0221(11) Uani 1 1 d . . . O7 O 0.5722(2) 0.8203(3) 0.7463(3) 0.0209(11) Uani 1 1 d . . . O8 O 0.6407(2) 0.7976(3) 0.6953(3) 0.0186(10) Uani 1 1 d . . . O9 O 0.4957(3) 0.6543(3) 0.3602(4) 0.0300(13) Uani 1 1 d . . . O10 O 0.1911(4) 0.5463(4) 0.2991(5) 0.0560(11) Uani 1 1 d . . . O11 O 0.1356(3) 0.5644(4) 0.4139(5) 0.0477(9) Uani 1 1 d . . . O1W O 0.2553(10) 0.6564(17) 0.1668(17) 0.045(7) Uani 0.25 1 d PU . . 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 Er1 0.01158(17) 0.01594(18) 0.01172(16) 0.00085(13) 0.00444(13) 0.00125(12) C1 0.018(4) 0.026(4) 0.015(3) -0.004(3) 0.005(3) 0.001(3) C2 0.030(4) 0.033(5) 0.021(4) 0.000(3) 0.018(4) -0.005(3) C3 0.029(4) 0.022(4) 0.028(4) -0.008(3) 0.022(4) -0.005(3) C4 0.026(4) 0.031(5) 0.022(4) -0.014(3) 0.018(3) -0.011(3) C5 0.022(4) 0.032(5) 0.023(4) -0.005(4) 0.002(3) -0.002(3) C6 0.031(4) 0.025(4) 0.023(4) -0.003(3) 0.009(4) -0.007(3) C7 0.018(4) 0.022(4) 0.014(3) -0.005(3) 0.010(3) -0.005(3) C8 0.015(3) 0.029(4) 0.013(3) -0.003(3) 0.007(3) -0.002(3) C9 0.022(4) 0.012(4) 0.018(3) 0.001(3) 0.011(3) 0.002(3) C10 0.016(4) 0.028(4) 0.010(3) -0.002(3) 0.005(3) -0.001(3) C11 0.019(4) 0.016(4) 0.010(3) -0.003(3) 0.006(3) 0.002(3) C12 0.010(3) 0.021(4) 0.019(4) -0.004(3) 0.005(3) -0.004(3) C13 0.020(4) 0.017(4) 0.018(4) -0.005(3) 0.007(3) -0.004(3) C14 0.020(4) 0.023(4) 0.016(3) 0.003(3) 0.009(3) 0.001(3) C15 0.014(3) 0.014(3) 0.008(3) 0.000(3) 0.001(3) 0.001(3) C16 0.064(3) 0.045(3) 0.043(2) -0.006(2) 0.020(2) 0.024(2) C17 0.064(3) 0.045(3) 0.043(2) -0.006(2) 0.020(2) 0.024(2) C17' 0.064(3) 0.045(3) 0.043(2) -0.006(2) 0.020(2) 0.024(2) C18 0.064(3) 0.045(3) 0.043(2) -0.006(2) 0.020(2) 0.024(2) C19 0.048(2) 0.040(2) 0.057(2) 0.0061(18) 0.030(2) -0.0093(17) C20 0.048(2) 0.040(2) 0.057(2) 0.0061(18) 0.030(2) -0.0093(17) C21 0.048(2) 0.040(2) 0.057(2) 0.0061(18) 0.030(2) -0.0093(17) N1 0.046(4) 0.029(4) 0.034(4) -0.012(3) 0.025(4) -0.014(3) N2 0.064(3) 0.045(3) 0.043(2) -0.006(2) 0.020(2) 0.024(2) N3 0.048(2) 0.040(2) 0.057(2) 0.0061(18) 0.030(2) -0.0093(17) O1 0.027(3) 0.017(3) 0.018(2) -0.002(2) 0.008(2) -0.003(2) O2 0.022(3) 0.016(3) 0.017(2) -0.002(2) 0.006(2) -0.003(2) O3 0.062(5) 0.033(4) 0.040(4) 0.002(3) 0.016(4) -0.005(3) O4 0.108(6) 0.024(4) 0.063(5) -0.014(3) 0.053(5) -0.017(4) O5 0.014(2) 0.033(3) 0.019(3) -0.001(2) 0.009(2) -0.003(2) O6 0.022(3) 0.032(3) 0.018(2) 0.001(2) 0.014(2) 0.004(2) O7 0.015(2) 0.030(3) 0.015(2) -0.006(2) 0.007(2) -0.001(2) O8 0.010(2) 0.026(3) 0.016(2) -0.004(2) 0.005(2) -0.0009(19) O9 0.023(3) 0.041(4) 0.034(3) -0.023(3) 0.021(3) -0.016(2) O10 0.064(3) 0.045(3) 0.043(2) -0.006(2) 0.020(2) 0.024(2) O11 0.048(2) 0.040(2) 0.057(2) 0.0061(18) 0.030(2) -0.0093(17) O1W 0.011(10) 0.09(2) 0.033(13) -0.017(12) 0.011(10) 0.011(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 Er1 O6 2.259(4) 7_566 ? Er1 O10 2.320(6) . ? Er1 O5 2.324(4) . ? Er1 O1 2.325(5) 4 ? Er1 O2 2.334(5) 6_566 ? Er1 O7 2.338(5) 8_465 ? Er1 O11 2.381(6) . ? Er1 O8 2.469(4) 8_465 ? Er1 C15 2.752(6) 8_465 ? C1 C2 1.387(10) . ? C1 C6 1.396(10) . ? C1 C13 1.501(9) . ? C2 C3 1.374(10) . ? C3 C4 1.399(10) . ? C3 N1 1.440(10) . ? C4 C5 1.379(11) . ? C4 O9 1.381(8) . ? C5 C6 1.380(10) . ? C7 C8 1.374(9) . ? C7 C12 1.375(9) . ? C7 O9 1.387(8) . ? C8 C9 1.396(9) . ? C9 C10 1.374(9) . ? C9 C14 1.492(9) . ? C10 C11 1.387(9) . ? C11 C12 1.385(9) . ? C11 C15 1.499(9) . ? C13 O1 1.248(8) . ? C13 O2 1.255(8) . ? C14 O6 1.252(8) . ? C14 O5 1.254(8) . ? C15 O8 1.263(8) . ? C15 O7 1.267(8) . ? C15 Er1 2.752(6) 8_566 ? C16 O10 1.151(10) . ? C16 N2 1.292(11) . ? C17 N2 1.506(19) . ? C17' N2 1.52(2) . ? C18 N2 1.421(11) . ? C19 O11 1.230(10) . ? C19 N3 1.331(11) . ? C20 N3 1.434(12) . ? C21 N3 1.433(11) . ? N1 O4 1.206(9) . ? N1 O3 1.234(9) . ? O1 Er1 2.325(5) 4_545 ? O2 Er1 2.334(5) 6_565 ? O6 Er1 2.259(4) 7_566 ? O7 Er1 2.338(5) 8_566 ? O8 Er1 2.469(4) 8_566 ? 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 O6 Er1 O10 146.6(2) 7_566 . ? O6 Er1 O5 122.65(17) 7_566 . ? O10 Er1 O5 77.5(2) . . ? O6 Er1 O1 71.38(17) 7_566 4 ? O10 Er1 O1 141.1(2) . 4 ? O5 Er1 O1 84.91(17) . 4 ? O6 Er1 O2 80.72(17) 7_566 6_566 ? O10 Er1 O2 79.46(19) . 6_566 ? O5 Er1 O2 75.49(17) . 6_566 ? O1 Er1 O2 129.20(17) 4 6_566 ? O6 Er1 O7 95.78(17) 7_566 8_465 ? O10 Er1 O7 86.7(2) . 8_465 ? O5 Er1 O7 130.42(16) . 8_465 ? O1 Er1 O7 78.80(17) 4 8_465 ? O2 Er1 O7 147.05(16) 6_566 8_465 ? O6 Er1 O11 75.7(2) 7_566 . ? O10 Er1 O11 72.9(2) . . ? O5 Er1 O11 139.8(2) . . ? O1 Er1 O11 134.8(2) 4 . ? O2 Er1 O11 72.9(2) 6_566 . ? O7 Er1 O11 74.52(19) 8_465 . ? O6 Er1 O8 135.10(16) 7_566 8_465 ? O10 Er1 O8 71.8(2) . 8_465 ? O5 Er1 O8 76.05(15) . 8_465 ? O1 Er1 O8 70.37(16) 4 8_465 ? O2 Er1 O8 143.11(15) 6_566 8_465 ? O7 Er1 O8 54.37(15) 8_465 8_465 ? O11 Er1 O8 118.12(19) . 8_465 ? O6 Er1 C15 115.24(19) 7_566 8_465 ? O10 Er1 C15 80.6(2) . 8_465 ? O5 Er1 C15 103.21(18) . 8_465 ? O1 Er1 C15 70.00(18) 4 8_465 ? O2 Er1 C15 159.78(18) 6_566 8_465 ? O7 Er1 C15 27.31(17) 8_465 8_465 ? O11 Er1 C15 98.2(2) . 8_465 ? O8 Er1 C15 27.31(16) 8_465 8_465 ? C2 C1 C6 118.6(7) . . ? C2 C1 C13 121.6(6) . . ? C6 C1 C13 119.9(7) . . ? C3 C2 C1 121.5(7) . . ? C2 C3 C4 119.8(7) . . ? C2 C3 N1 118.5(7) . . ? C4 C3 N1 121.7(7) . . ? C5 C4 O9 118.2(7) . . ? C5 C4 C3 118.6(7) . . ? O9 C4 C3 123.1(7) . . ? C4 C5 C6 121.6(7) . . ? C5 C6 C1 119.7(8) . . ? C8 C7 C12 121.3(6) . . ? C8 C7 O9 122.3(6) . . ? C12 C7 O9 116.4(6) . . ? C7 C8 C9 119.6(6) . . ? C10 C9 C8 119.7(6) . . ? C10 C9 C14 121.3(6) . . ? C8 C9 C14 119.1(6) . . ? C9 C10 C11 119.8(6) . . ? C12 C11 C10 120.8(6) . . ? C12 C11 C15 119.5(6) . . ? C10 C11 C15 119.7(6) . . ? C7 C12 C11 118.7(6) . . ? O1 C13 O2 127.1(6) . . ? O1 C13 C1 115.9(6) . . ? O2 C13 C1 117.0(6) . . ? O6 C14 O5 122.1(6) . . ? O6 C14 C9 119.1(6) . . ? O5 C14 C9 118.9(6) . . ? O8 C15 O7 120.7(6) . . ? O8 C15 C11 119.3(6) . . ? O7 C15 C11 119.9(6) . . ? O8 C15 Er1 63.8(3) . 8_566 ? O7 C15 Er1 57.8(3) . 8_566 ? C11 C15 Er1 167.9(5) . 8_566 ? O10 C16 N2 132.2(10) . . ? O11 C19 N3 123.7(9) . . ? O4 N1 O3 123.0(8) . . ? O4 N1 C3 120.1(7) . . ? O3 N1 C3 116.9(6) . . ? C16 N2 C18 117.1(8) . . ? C16 N2 C17 118.6(11) . . ? C18 N2 C17 118.1(9) . . ? C16 N2 C17' 133.4(11) . . ? C18 N2 C17' 105.3(10) . . ? C17 N2 C17' 46.0(11) . . ? C19 N3 C21 121.1(8) . . ? C19 N3 C20 119.7(8) . . ? C21 N3 C20 119.1(7) . . ? C13 O1 Er1 141.1(4) . 4_545 ? C13 O2 Er1 136.5(4) . 6_565 ? C14 O5 Er1 110.3(4) . . ? C14 O6 Er1 171.9(5) . 7_566 ? C15 O7 Er1 94.9(4) . 8_566 ? C15 O8 Er1 88.9(4) . 8_566 ? C4 O9 C7 115.8(5) . . ? C16 O10 Er1 133.3(7) . . ? C19 O11 Er1 137.4(6) . . ? _diffrn_measured_fraction_theta_max 0.990 _diffrn_reflns_theta_full 26.18 _diffrn_measured_fraction_theta_full 0.990 _refine_diff_density_max 2.697 _refine_diff_density_min -2.370 _refine_diff_density_rms 0.183 data_12 _database_code_depnum_ccdc_archive 'CCDC 857013' #TrackingRef '- 1-12 and 7.CIF' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point 'not measured' _chemical_formula_moiety 'C21 H20.50 N3 O11.25 Tm' _chemical_formula_sum 'C21 H20.50 N3 O11.25 Tm' _chemical_formula_weight 663.83 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' Tm Tm -0.3139 5.2483 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Monoclinic _symmetry_space_group_name_H-M C2/c loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y, -z+1/2' 'x+1/2, y+1/2, z' '-x+1/2, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y, z-1/2' '-x+1/2, -y+1/2, -z' 'x+1/2, -y+1/2, z-1/2' _cell_length_a 23.560(4) _cell_length_b 15.660(3) _cell_length_c 15.991(5) _cell_angle_alpha 90.00 _cell_angle_beta 123.957(2) _cell_angle_gamma 90.00 _cell_volume 4893.6(19) _cell_formula_units_Z 8 _cell_measurement_temperature 185(2) _cell_measurement_reflns_used 4860 _cell_measurement_theta_min 1.67 _cell_measurement_theta_max 26.09 _exptl_crystal_description rod _exptl_crystal_colour 'light yellow' _exptl_crystal_size_max 0.17 _exptl_crystal_size_mid 0.13 _exptl_crystal_size_min 0.12 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.802 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 2612 _exptl_absorpt_coefficient_mu 3.691 _exptl_absorpt_correction_type empirical _exptl_absorpt_correction_T_min 0.5726 _exptl_absorpt_correction_T_max 0.6657 _exptl_absorpt_process_details SADABS _exptl_special_details ; ? ; _diffrn_ambient_temperature 185(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'CCD area detector' _diffrn_measurement_method 'phi and omega scans' _diffrn_detector_area_resol_mean 9.00cm _diffrn_standards_number none _diffrn_standards_interval_count none _diffrn_standards_interval_time none _diffrn_standards_decay_% none _diffrn_reflns_number 13137 _diffrn_reflns_av_R_equivalents 0.0482 _diffrn_reflns_av_sigmaI/netI 0.0592 _diffrn_reflns_limit_h_min -29 _diffrn_reflns_limit_h_max 29 _diffrn_reflns_limit_k_min -19 _diffrn_reflns_limit_k_max 11 _diffrn_reflns_limit_l_min -18 _diffrn_reflns_limit_l_max 19 _diffrn_reflns_theta_min 1.67 _diffrn_reflns_theta_max 26.09 _reflns_number_total 4860 _reflns_number_gt 3849 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SMART' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics SHELXP-97 _computing_publication_material SHELXTL _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0433P)^2^+40.1158P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 4860 _refine_ls_number_parameters 289 _refine_ls_number_restraints 6 _refine_ls_R_factor_all 0.0563 _refine_ls_R_factor_gt 0.0413 _refine_ls_wR_factor_ref 0.1027 _refine_ls_wR_factor_gt 0.0933 _refine_ls_goodness_of_fit_ref 1.022 _refine_ls_restrained_S_all 1.022 _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 Tm1 Tm 0.189230(13) 0.171910(17) 0.374199(19) 0.01550(10) Uani 1 1 d . . . C1 C 0.1348(3) 0.4586(4) 0.3289(5) 0.0243(15) Uani 1 1 d . . . C2 C 0.1459(4) 0.5409(4) 0.3651(5) 0.0250(15) Uani 1 1 d . . . H2A H 0.1825 0.5527 0.4326 0.030 Uiso 1 1 calc R . . C3 C 0.1038(3) 0.6064(4) 0.3035(5) 0.0236(15) Uani 1 1 d . . . C4 C 0.0499(3) 0.5909(5) 0.2050(5) 0.0256(16) Uani 1 1 d . . . C5 C 0.0374(4) 0.5076(5) 0.1699(5) 0.0315(17) Uani 1 1 d . . . H5A H -0.0008 0.4956 0.1037 0.038 Uiso 1 1 calc R . . C6 C 0.0794(4) 0.4420(5) 0.2297(5) 0.0327(17) Uani 1 1 d . . . H6A H 0.0710 0.3854 0.2040 0.039 Uiso 1 1 calc R . . C7 C 0.0200(3) 0.6894(4) 0.0755(5) 0.0217(15) Uani 1 1 d . . . C8 C 0.0853(3) 0.6897(4) 0.0956(5) 0.0226(15) Uani 1 1 d . . . H8A H 0.1222 0.6648 0.1560 0.027 Uiso 1 1 calc R . . C9 C 0.0965(3) 0.7265(4) 0.0272(5) 0.0189(14) Uani 1 1 d . . . C10 C 0.0413(3) 0.7596(4) -0.0634(5) 0.0203(14) Uani 1 1 d . . . H10A H 0.0482 0.7818 -0.1124 0.024 Uiso 1 1 calc R . . C11 C -0.0233(3) 0.7598(4) -0.0814(5) 0.0172(13) Uani 1 1 d . . . C12 C -0.0345(3) 0.7246(4) -0.0116(5) 0.0205(14) Uani 1 1 d . . . H12A H -0.0789 0.7249 -0.0241 0.025 Uiso 1 1 calc R . . C13 C 0.1820(3) 0.3867(4) 0.3922(5) 0.0233(15) Uani 1 1 d . . . C14 C 0.1675(3) 0.7297(4) 0.0514(5) 0.0216(14) Uani 1 1 d . . . C15 C -0.0826(3) 0.7946(4) -0.1798(5) 0.0192(14) Uani 1 1 d . . . C16 C 0.2314(5) -0.0100(6) 0.3277(7) 0.0589(11) Uani 1 1 d . A . H16 H 0.2688 -0.0064 0.3962 0.088 Uiso 1 1 calc R . . C17 C 0.2974(11) -0.1253(13) 0.3277(14) 0.0589(11) Uani 0.50 1 d P A 1 H17A H 0.3329 -0.0862 0.3368 0.088 Uiso 0.50 1 calc PR A 1 H17B H 0.2922 -0.1725 0.2835 0.088 Uiso 0.50 1 calc PR A 1 H17C H 0.3107 -0.1481 0.3933 0.088 Uiso 0.50 1 calc PR A 1 C17' C 0.2531(11) -0.1675(12) 0.3149(14) 0.0589(11) Uani 0.50 1 d P A 2 H17D H 0.2142 -0.2014 0.3026 0.088 Uiso 0.50 1 calc PR A 2 H17E H 0.2892 -0.1677 0.3872 0.088 Uiso 0.50 1 calc PR A 2 H17F H 0.2709 -0.1923 0.2776 0.088 Uiso 0.50 1 calc PR A 2 C18 C 0.1820(5) -0.0829(6) 0.1746(6) 0.0589(11) Uani 1 1 d . A . H18A H 0.1417 -0.0487 0.1557 0.088 Uiso 1 1 calc R . . H18B H 0.1683 -0.1426 0.1552 0.088 Uiso 1 1 calc R . . H18C H 0.2025 -0.0610 0.1399 0.088 Uiso 1 1 calc R . . C19 C 0.0779(5) 0.0420(6) 0.3840(7) 0.0509(9) Uani 1 1 d . A . H19A H 0.0414 0.0795 0.3401 0.061 Uiso 1 1 calc R . . C20 C 0.1158(5) -0.0901(6) 0.4767(7) 0.0509(9) Uani 1 1 d . . . H20A H 0.1605 -0.0671 0.4972 0.076 Uiso 1 1 calc R . . H20B H 0.1077 -0.1440 0.4407 0.076 Uiso 1 1 calc R . . H20C H 0.1152 -0.1001 0.5367 0.076 Uiso 1 1 calc R . . C21 C -0.0077(4) -0.0504(6) 0.3713(7) 0.0509(9) Uani 1 1 d . . . H21A H -0.0376 -0.0037 0.3286 0.076 Uiso 1 1 calc R . . H21B H -0.0131 -0.0593 0.4272 0.076 Uiso 1 1 calc R . . H21C H -0.0203 -0.1028 0.3311 0.076 Uiso 1 1 calc R . . N1 N 0.1190(3) 0.6920(4) 0.3469(5) 0.0352(15) Uani 1 1 d . . . N2 N 0.2305(4) -0.0780(5) 0.2805(6) 0.0589(11) Uani 1 1 d . . . N3 N 0.0625(4) -0.0292(5) 0.4108(6) 0.0509(9) Uani 1 1 d . . . O1 O 0.1758(2) 0.3184(3) 0.3472(3) 0.0244(11) Uani 1 1 d . . . O2 O 0.2241(2) 0.4014(3) 0.4851(3) 0.0223(10) Uani 1 1 d . . . O3 O 0.1536(3) 0.6987(4) 0.4394(5) 0.0536(17) Uani 1 1 d . . . O4 O 0.0970(4) 0.7535(4) 0.2907(5) 0.062(2) Uani 1 1 d . . . O5 O 0.2148(2) 0.6924(3) 0.1295(3) 0.0249(11) Uani 1 1 d . . . O6 O 0.1776(2) 0.7697(3) -0.0077(3) 0.0243(11) Uani 1 1 d . . . O7 O -0.0725(2) 0.8188(3) -0.2459(3) 0.0244(11) Uani 1 1 d . . . O8 O -0.1406(2) 0.7970(3) -0.1947(3) 0.0216(10) Uani 1 1 d . . . O9 O 0.0052(2) 0.6538(3) 0.1411(4) 0.0317(12) Uani 1 1 d . . . O10 O 0.1927(3) 0.0479(4) 0.2986(4) 0.0589(11) Uani 1 1 d . . . O11 O 0.1362(3) 0.0632(4) 0.4119(5) 0.0509(9) Uani 1 1 d . . . O1W O 0.2457(10) 0.6565(15) 0.3339(16) 0.038(5) Uani 0.25 1 d PU . . 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 Tm1 0.01434(15) 0.01417(15) 0.01308(15) 0.00078(12) 0.00463(11) 0.00118(12) C1 0.028(4) 0.021(4) 0.021(3) 0.006(3) 0.012(3) 0.005(3) C2 0.031(4) 0.020(4) 0.022(3) 0.000(3) 0.014(3) 0.001(3) C3 0.027(4) 0.018(3) 0.033(4) 0.003(3) 0.021(3) 0.003(3) C4 0.025(4) 0.030(4) 0.023(4) 0.015(3) 0.015(3) 0.013(3) C5 0.028(4) 0.030(4) 0.024(4) 0.006(3) 0.006(3) 0.004(3) C6 0.034(4) 0.027(4) 0.022(4) 0.003(3) 0.006(3) 0.005(3) C7 0.026(3) 0.018(3) 0.022(3) 0.009(3) 0.014(3) 0.007(3) C8 0.023(3) 0.024(4) 0.020(3) 0.008(3) 0.012(3) 0.006(3) C9 0.016(3) 0.021(3) 0.019(3) 0.003(3) 0.009(3) 0.002(3) C10 0.022(3) 0.022(3) 0.014(3) 0.004(3) 0.008(3) 0.004(3) C11 0.020(3) 0.015(3) 0.015(3) 0.002(3) 0.008(3) 0.001(3) C12 0.020(3) 0.021(3) 0.021(3) 0.003(3) 0.012(3) 0.002(3) C13 0.028(4) 0.013(3) 0.027(4) 0.008(3) 0.014(3) 0.003(3) C14 0.025(3) 0.018(3) 0.022(3) -0.009(3) 0.013(3) -0.005(3) C15 0.017(3) 0.017(3) 0.017(3) -0.005(3) 0.006(3) -0.006(3) C16 0.074(3) 0.045(2) 0.043(2) -0.0093(19) 0.023(2) 0.026(2) C17 0.074(3) 0.045(2) 0.043(2) -0.0093(19) 0.023(2) 0.026(2) C17' 0.074(3) 0.045(2) 0.043(2) -0.0093(19) 0.023(2) 0.026(2) C18 0.074(3) 0.045(2) 0.043(2) -0.0093(19) 0.023(2) 0.026(2) C19 0.055(2) 0.040(2) 0.059(2) 0.0050(18) 0.033(2) -0.0117(17) C20 0.055(2) 0.040(2) 0.059(2) 0.0050(18) 0.033(2) -0.0117(17) C21 0.055(2) 0.040(2) 0.059(2) 0.0050(18) 0.033(2) -0.0117(17) N1 0.048(4) 0.023(3) 0.037(4) 0.009(3) 0.025(3) 0.008(3) N2 0.074(3) 0.045(2) 0.043(2) -0.0093(19) 0.023(2) 0.026(2) N3 0.055(2) 0.040(2) 0.059(2) 0.0050(18) 0.033(2) -0.0117(17) O1 0.033(3) 0.012(2) 0.022(2) 0.0025(19) 0.012(2) 0.003(2) O2 0.018(2) 0.020(2) 0.015(2) 0.0006(19) 0.0011(19) 0.0025(19) O3 0.066(4) 0.032(3) 0.041(4) -0.002(3) 0.016(3) 0.005(3) O4 0.109(6) 0.029(3) 0.053(4) 0.016(3) 0.048(4) 0.022(4) O5 0.016(2) 0.032(3) 0.021(2) 0.003(2) 0.007(2) 0.004(2) O6 0.025(2) 0.029(3) 0.021(2) 0.000(2) 0.014(2) -0.002(2) O7 0.020(2) 0.034(3) 0.014(2) 0.007(2) 0.0067(19) -0.001(2) O8 0.016(2) 0.023(2) 0.020(2) 0.002(2) 0.0066(19) 0.0017(19) O9 0.029(3) 0.040(3) 0.035(3) 0.027(2) 0.024(2) 0.019(2) O10 0.074(3) 0.045(2) 0.043(2) -0.0093(19) 0.023(2) 0.026(2) O11 0.055(2) 0.040(2) 0.059(2) 0.0050(18) 0.033(2) -0.0117(17) O1W 0.036(8) 0.056(10) 0.035(8) 0.015(7) 0.028(7) -0.008(7) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag Tm1 O6 2.248(5) 6_566 ? Tm1 O10 2.312(6) . ? Tm1 O5 2.318(4) 4_545 ? Tm1 O1 2.324(4) . ? Tm1 O2 2.327(4) 7_556 ? Tm1 O7 2.343(4) 5_565 ? Tm1 O11 2.380(6) . ? Tm1 O8 2.472(4) 5_565 ? Tm1 C15 2.743(6) 5_565 ? C1 C2 1.377(9) . ? C1 C6 1.404(9) . ? C1 C13 1.508(9) . ? C2 C3 1.383(9) . ? C3 C4 1.385(10) . ? C3 N1 1.459(9) . ? C4 O9 1.386(8) . ? C4 C5 1.386(10) . ? C5 C6 1.376(10) . ? C7 C12 1.376(9) . ? C7 C8 1.384(9) . ? C7 O9 1.393(8) . ? C8 C9 1.385(9) . ? C9 C10 1.397(9) . ? C9 C14 1.494(9) . ? C10 C11 1.382(9) . ? C11 C12 1.395(9) . ? C11 C15 1.507(9) . ? C13 O1 1.252(8) . ? C13 O2 1.264(8) . ? C14 O5 1.260(8) . ? C14 O6 1.262(8) . ? C15 O8 1.250(7) . ? C15 O7 1.263(8) . ? C15 Tm1 2.743(6) 5_565 ? C16 O10 1.182(10) . ? C16 N2 1.298(11) . ? C17 N2 1.510(19) . ? C17' N2 1.493(19) . ? C18 N2 1.420(11) . ? C19 O11 1.230(10) . ? C19 N3 1.316(10) . ? C20 N3 1.457(11) . ? C21 N3 1.442(10) . ? N1 O4 1.219(8) . ? N1 O3 1.231(8) . ? O2 Tm1 2.327(4) 7_556 ? O5 Tm1 2.318(4) 4 ? O6 Tm1 2.248(5) 6_565 ? O7 Tm1 2.343(4) 5_565 ? O8 Tm1 2.472(4) 5_565 ? 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 O6 Tm1 O10 146.8(2) 6_566 . ? O6 Tm1 O5 122.93(16) 6_566 4_545 ? O10 Tm1 O5 77.5(2) . 4_545 ? O6 Tm1 O1 71.76(17) 6_566 . ? O10 Tm1 O1 140.6(2) . . ? O5 Tm1 O1 83.77(17) 4_545 . ? O6 Tm1 O2 80.90(16) 6_566 7_556 ? O10 Tm1 O2 79.80(19) . 7_556 ? O5 Tm1 O2 75.58(16) 4_545 7_556 ? O1 Tm1 O2 128.42(16) . 7_556 ? O6 Tm1 O7 94.37(16) 6_566 5_565 ? O10 Tm1 O7 87.8(2) . 5_565 ? O5 Tm1 O7 130.81(16) 4_545 5_565 ? O1 Tm1 O7 78.73(16) . 5_565 ? O2 Tm1 O7 147.60(16) 7_556 5_565 ? O6 Tm1 O11 75.5(2) 6_566 . ? O10 Tm1 O11 73.1(2) . . ? O5 Tm1 O11 139.80(19) 4_545 . ? O1 Tm1 O11 135.82(19) . . ? O2 Tm1 O11 72.79(19) 7_556 . ? O7 Tm1 O11 74.98(19) 5_565 . ? O6 Tm1 O8 134.42(16) 6_566 5_565 ? O10 Tm1 O8 71.79(19) . 5_565 ? O5 Tm1 O8 76.65(15) 4_545 5_565 ? O1 Tm1 O8 70.30(16) . 5_565 ? O2 Tm1 O8 143.75(15) 7_556 5_565 ? O7 Tm1 O8 54.19(14) 5_565 5_565 ? O11 Tm1 O8 117.81(18) . 5_565 ? O6 Tm1 C15 114.19(18) 6_566 5_565 ? O10 Tm1 C15 81.1(2) . 5_565 ? O5 Tm1 C15 103.52(18) 4_545 5_565 ? O1 Tm1 C15 69.96(18) . 5_565 ? O2 Tm1 C15 160.62(18) 7_556 5_565 ? O7 Tm1 C15 27.32(17) 5_565 5_565 ? O11 Tm1 C15 98.4(2) . 5_565 ? O8 Tm1 C15 27.11(16) 5_565 5_565 ? C2 C1 C6 119.2(6) . . ? C2 C1 C13 121.3(6) . . ? C6 C1 C13 119.4(6) . . ? C1 C2 C3 120.1(6) . . ? C2 C3 C4 121.2(6) . . ? C2 C3 N1 117.0(6) . . ? C4 C3 N1 121.8(6) . . ? C3 C4 O9 123.5(7) . . ? C3 C4 C5 118.5(6) . . ? O9 C4 C5 117.9(6) . . ? C6 C5 C4 120.9(7) . . ? C5 C6 C1 120.0(7) . . ? C12 C7 C8 121.4(6) . . ? C12 C7 O9 116.0(6) . . ? C8 C7 O9 122.6(6) . . ? C7 C8 C9 119.6(6) . . ? C8 C9 C10 119.8(6) . . ? C8 C9 C14 119.3(6) . . ? C10 C9 C14 121.0(6) . . ? C11 C10 C9 119.7(6) . . ? C10 C11 C12 120.7(6) . . ? C10 C11 C15 119.3(6) . . ? C12 C11 C15 120.0(6) . . ? C7 C12 C11 118.8(6) . . ? O1 C13 O2 126.5(6) . . ? O1 C13 C1 116.5(6) . . ? O2 C13 C1 117.0(6) . . ? O5 C14 O6 122.8(6) . . ? O5 C14 C9 118.8(6) . . ? O6 C14 C9 118.4(6) . . ? O8 C15 O7 121.8(6) . . ? O8 C15 C11 119.2(6) . . ? O7 C15 C11 119.0(6) . . ? O8 C15 Tm1 64.3(3) . 5_565 ? O7 C15 Tm1 58.4(3) . 5_565 ? C11 C15 Tm1 168.8(5) . 5_565 ? O10 C16 N2 129.9(9) . . ? O11 C19 N3 124.5(9) . . ? O4 N1 O3 122.8(7) . . ? O4 N1 C3 119.0(7) . . ? O3 N1 C3 118.2(6) . . ? C16 N2 C18 118.6(8) . . ? C16 N2 C17' 132.0(10) . . ? C18 N2 C17' 105.8(10) . . ? C16 N2 C17 116.1(10) . . ? C18 N2 C17 119.3(9) . . ? C17' N2 C17 45.2(11) . . ? C19 N3 C21 120.7(8) . . ? C19 N3 C20 120.4(8) . . ? C21 N3 C20 118.8(7) . . ? C13 O1 Tm1 140.9(4) . . ? C13 O2 Tm1 137.3(4) . 7_556 ? C14 O5 Tm1 111.9(4) . 4 ? C14 O6 Tm1 173.2(4) . 6_565 ? C15 O7 Tm1 94.3(4) . 5_565 ? C15 O8 Tm1 88.6(4) . 5_565 ? C4 O9 C7 115.7(5) . . ? C16 O10 Tm1 133.1(6) . . ? C19 O11 Tm1 137.7(6) . . ? _diffrn_measured_fraction_theta_max 0.997 _diffrn_reflns_theta_full 26.09 _diffrn_measured_fraction_theta_full 0.997 _refine_diff_density_max 2.430 _refine_diff_density_min -2.174 _refine_diff_density_rms 0.169 data_7' _database_code_depnum_ccdc_archive 'CCDC 857014' #TrackingRef '- 1-12 and 7.CIF' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point 'not measured' _chemical_formula_moiety 'C15 H12 Gd N O12' _chemical_formula_sum 'C15 H12 Gd N O12' _chemical_formula_weight 555.51 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' Gd Gd -0.1653 3.9035 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Monoclinic _symmetry_space_group_name_H-M P2(1)/c loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y-1/2, z-1/2' _cell_length_a 5.4387(5) _cell_length_b 29.037(3) _cell_length_c 10.9220(10) _cell_angle_alpha 90.00 _cell_angle_beta 93.882(2) _cell_angle_gamma 90.00 _cell_volume 1720.9(3) _cell_formula_units_Z 4 _cell_measurement_temperature 185(2) _cell_measurement_reflns_used 3405 _cell_measurement_theta_min 1.40 _cell_measurement_theta_max 26.07 _exptl_crystal_description block _exptl_crystal_colour 'light yellow' _exptl_crystal_size_max 0.16 _exptl_crystal_size_mid 0.11 _exptl_crystal_size_min 0.10 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 2.144 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1076 _exptl_absorpt_coefficient_mu 3.926 _exptl_absorpt_correction_type empirical _exptl_absorpt_correction_T_min 0.5723 _exptl_absorpt_correction_T_max 0.6949 _exptl_absorpt_process_details SADABS _exptl_special_details ; ? ; _diffrn_ambient_temperature 185(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'CCD area detector' _diffrn_measurement_method 'phi and omega scans' _diffrn_detector_area_resol_mean 9.00cm _diffrn_standards_number none _diffrn_standards_interval_count none _diffrn_standards_interval_time none _diffrn_standards_decay_% none _diffrn_reflns_number 8813 _diffrn_reflns_av_R_equivalents 0.0743 _diffrn_reflns_av_sigmaI/netI 0.1028 _diffrn_reflns_limit_h_min -6 _diffrn_reflns_limit_h_max 6 _diffrn_reflns_limit_k_min -33 _diffrn_reflns_limit_k_max 35 _diffrn_reflns_limit_l_min -13 _diffrn_reflns_limit_l_max 10 _diffrn_reflns_theta_min 1.40 _diffrn_reflns_theta_max 26.07 _reflns_number_total 3405 _reflns_number_gt 2449 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SMART' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics SHELXP-97 _computing_publication_material SHELXTL _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.1326P)^2^+4.6346P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment mixed _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 3405 _refine_ls_number_parameters 280 _refine_ls_number_restraints 28 _refine_ls_R_factor_all 0.1035 _refine_ls_R_factor_gt 0.0777 _refine_ls_wR_factor_ref 0.2338 _refine_ls_wR_factor_gt 0.1991 _refine_ls_goodness_of_fit_ref 1.092 _refine_ls_restrained_S_all 1.092 _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 Gd1 Gd 0.00419(11) 0.423848(19) 0.78159(6) 0.0192(3) Uani 1 1 d D . . C1 C 0.328(2) 0.4097(4) 1.1520(13) 0.020(3) Uani 1 1 d . . . C2 C 0.279(3) 0.3721(4) 1.2262(14) 0.026(3) Uani 1 1 d . . . H2A H 0.1550 0.3504 1.2008 0.032 Uiso 1 1 calc R . . C3 C 0.415(2) 0.3670(4) 1.3380(13) 0.020(3) Uani 1 1 d U . . C4 C 0.602(3) 0.3972(4) 1.3744(14) 0.026(3) Uani 1 1 d . . . H4A H 0.6972 0.3923 1.4495 0.032 Uiso 1 1 calc R . . C5 C 0.652(2) 0.4351(4) 1.3008(13) 0.021(3) Uani 1 1 d . . . C6 C 0.515(3) 0.4406(5) 1.1921(13) 0.024(3) Uani 1 1 d . . . H6A H 0.5476 0.4663 1.1417 0.029 Uiso 1 1 calc R . . C7 C 0.392(2) 0.2877(4) 1.3828(13) 0.020(3) Uani 1 1 d . . . C8 C 0.267(3) 0.2516(4) 1.4342(13) 0.024(3) Uani 1 1 d . . . C9 C 0.305(2) 0.2066(4) 1.4031(13) 0.024(3) Uani 1 1 d . . . H9A H 0.2111 0.1829 1.4379 0.029 Uiso 1 1 calc R . . C10 C 0.483(3) 0.1953(4) 1.3192(12) 0.021(3) Uani 1 1 d . . . C11 C 0.609(3) 0.2307(4) 1.2720(14) 0.029(3) Uani 1 1 d . . . H11A H 0.7312 0.2237 1.2167 0.035 Uiso 1 1 calc R . . C12 C 0.569(3) 0.2767(5) 1.2997(14) 0.030(3) Uani 1 1 d . . . H12A H 0.6596 0.3003 1.2630 0.036 Uiso 1 1 calc R . . C13 C 0.185(3) 0.4169(4) 1.0323(14) 0.024(3) Uani 1 1 d U . . C14 C 0.535(2) 0.1461(4) 1.2919(12) 0.019(3) Uani 1 1 d . . . C15 C 0.846(2) 0.4707(4) 1.3346(14) 0.023(3) Uani 1 1 d . . . N1 N 0.086(2) 0.2603(4) 1.5213(12) 0.027(3) Uani 1 1 d . . . O1 O 0.2329(17) 0.4533(3) 0.9679(9) 0.024(2) Uani 1 1 d . . . O2 O 0.0302(17) 0.3881(3) 0.9952(9) 0.022(2) Uani 1 1 d . . . O3 O 0.014(3) 0.2986(4) 1.5402(15) 0.077(6) Uani 1 1 d . . . O4 O 0.011(2) 0.2280(4) 1.5794(13) 0.058(4) Uani 1 1 d U . . O5 O 0.3755(17) 0.1166(3) 1.3050(10) 0.027(2) Uani 1 1 d . . . O6 O 0.7423(17) 0.1375(3) 1.2561(9) 0.025(2) Uani 1 1 d . . . O7 O 1.0315(17) 0.4605(3) 1.3988(8) 0.022(2) Uani 1 1 d . . . O8 O 0.8041(17) 0.5103(3) 1.2881(9) 0.025(2) Uani 1 1 d . . . O9 O 0.3581(18) 0.3319(3) 1.4162(8) 0.024(2) Uani 1 1 d . . . O10 O -0.2784(17) 0.4635(3) 0.9034(10) 0.026(2) Uani 1 1 d D . . O11 O -0.3016(17) 0.4608(3) 0.6347(9) 0.024(2) Uani 1 1 d D . . O12 O 0.109(2) 0.3996(3) 0.5825(8) 0.025(2) Uani 1 1 d D . . H12C H 0.08(3) 0.408(4) 0.511(4) 0.030 Uiso 1 1 d D . . H12B H 0.13(3) 0.3715(8) 0.585(10) 0.030 Uiso 1 1 d D . . H11B H -0.25(2) 0.4870(16) 0.622(12) 0.030 Uiso 1 1 d D . . H11C H -0.39(2) 0.461(4) 0.693(9) 0.030 Uiso 1 1 d D . . H10C H -0.187(14) 0.4860(19) 0.905(12) 0.030 Uiso 1 1 d D . . H10B H -0.407(12) 0.470(2) 0.934(13) 0.030 Uiso 1 1 d D . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 Gd1 0.0187(4) 0.0100(4) 0.0286(5) 0.0008(3) -0.0005(3) -0.0012(2) C1 0.017(7) 0.016(6) 0.028(8) -0.001(6) 0.011(6) -0.003(5) C2 0.031(8) 0.008(6) 0.039(9) 0.002(6) -0.003(6) -0.003(5) C3 0.023(6) 0.007(5) 0.030(6) 0.006(5) 0.000(5) 0.003(5) C4 0.025(8) 0.022(7) 0.032(8) 0.000(6) 0.000(6) 0.000(6) C5 0.015(7) 0.016(6) 0.034(8) -0.001(6) 0.006(6) -0.002(5) C6 0.035(8) 0.018(6) 0.019(7) 0.001(6) 0.003(6) -0.005(6) C7 0.024(7) 0.006(5) 0.030(8) 0.001(5) -0.006(6) -0.006(5) C8 0.027(8) 0.018(6) 0.028(8) -0.002(6) 0.004(6) 0.006(6) C9 0.016(7) 0.021(7) 0.034(8) 0.000(6) -0.010(6) -0.007(5) C10 0.035(8) 0.008(6) 0.018(7) -0.003(5) -0.006(6) 0.004(5) C11 0.040(9) 0.015(6) 0.032(8) 0.007(6) 0.000(7) 0.011(6) C12 0.031(8) 0.020(7) 0.040(9) 0.010(6) 0.007(7) 0.000(6) C13 0.026(6) 0.016(5) 0.030(6) 0.004(5) -0.008(5) 0.014(5) C14 0.020(7) 0.014(6) 0.024(7) 0.004(5) 0.002(6) -0.001(5) C15 0.018(7) 0.010(6) 0.040(9) -0.003(6) -0.003(6) 0.001(5) N1 0.024(6) 0.014(5) 0.044(8) 0.001(5) 0.013(6) 0.002(5) O1 0.023(5) 0.009(4) 0.038(6) 0.004(4) -0.006(4) -0.005(4) O2 0.023(5) 0.009(4) 0.031(6) -0.007(4) -0.015(4) -0.003(4) O3 0.110(13) 0.015(6) 0.117(13) 0.000(7) 0.081(11) 0.003(7) O4 0.066(7) 0.046(6) 0.068(7) 0.011(6) 0.050(6) 0.007(5) O5 0.021(5) 0.014(4) 0.045(6) -0.002(4) -0.003(4) -0.006(4) O6 0.022(5) 0.016(4) 0.036(6) 0.003(4) 0.009(4) 0.006(4) O7 0.028(5) 0.008(4) 0.027(5) 0.005(4) -0.014(4) -0.001(4) O8 0.030(5) 0.015(4) 0.032(6) 0.004(4) 0.004(4) -0.004(4) O9 0.040(6) 0.009(4) 0.025(5) -0.002(4) 0.002(4) 0.002(4) O10 0.020(5) 0.017(4) 0.041(6) -0.008(4) 0.006(4) 0.001(4) O11 0.016(5) 0.019(4) 0.037(6) 0.001(4) 0.006(4) -0.001(4) O12 0.042(6) 0.023(5) 0.011(5) 0.002(4) 0.000(4) 0.003(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 Gd1 O6 2.286(9) 4_465 ? Gd1 O8 2.331(9) 3_667 ? Gd1 O5 2.335(9) 4_565 ? Gd1 O12 2.391(9) . ? Gd1 O10 2.395(9) . ? Gd1 O1 2.465(10) . ? Gd1 O11 2.475(10) . ? Gd1 O2 2.549(10) . ? C1 C2 1.397(18) . ? C1 C6 1.402(19) . ? C1 C13 1.49(2) . ? C2 C3 1.39(2) . ? C3 O9 1.377(15) . ? C3 C4 1.383(19) . ? C4 C5 1.400(19) . ? C5 C6 1.37(2) . ? C5 C15 1.506(18) . ? C7 O9 1.350(14) . ? C7 C8 1.390(18) . ? C7 C12 1.401(19) . ? C8 C9 1.369(18) . ? C8 N1 1.435(17) . ? C9 C10 1.419(19) . ? C10 C11 1.36(2) . ? C10 C14 1.489(17) . ? C11 C12 1.389(19) . ? C13 O2 1.237(16) . ? C13 O1 1.305(16) . ? C14 O5 1.234(15) . ? C14 O6 1.244(15) . ? C15 O7 1.224(16) . ? C15 O8 1.270(15) . ? N1 O3 1.202(14) . ? N1 O4 1.217(15) . ? O5 Gd1 2.335(9) 4_566 ? O6 Gd1 2.286(9) 4_666 ? O8 Gd1 2.331(9) 3_667 ? 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 O6 Gd1 O8 152.7(4) 4_465 3_667 ? O6 Gd1 O5 98.5(3) 4_465 4_565 ? O8 Gd1 O5 92.6(3) 3_667 4_565 ? O6 Gd1 O12 81.1(3) 4_465 . ? O8 Gd1 O12 78.8(3) 3_667 . ? O5 Gd1 O12 72.1(4) 4_565 . ? O6 Gd1 O10 91.4(3) 4_465 . ? O8 Gd1 O10 96.0(3) 3_667 . ? O5 Gd1 O10 139.8(4) 4_565 . ? O12 Gd1 O10 148.0(4) . . ? O6 Gd1 O1 130.2(3) 4_465 . ? O8 Gd1 O1 76.9(3) 3_667 . ? O5 Gd1 O1 72.5(3) 4_565 . ? O12 Gd1 O1 135.6(3) . . ? O10 Gd1 O1 71.4(3) . . ? O6 Gd1 O11 82.7(3) 4_465 . ? O8 Gd1 O11 74.2(3) 3_667 . ? O5 Gd1 O11 145.8(3) 4_565 . ? O12 Gd1 O11 74.3(3) . . ? O10 Gd1 O11 73.9(3) . . ? O1 Gd1 O11 131.6(3) . . ? O6 Gd1 O2 77.8(3) 4_465 . ? O8 Gd1 O2 129.4(3) 3_667 . ? O5 Gd1 O2 72.6(3) 4_565 . ? O12 Gd1 O2 135.2(3) . . ? O10 Gd1 O2 71.7(3) . . ? O1 Gd1 O2 52.6(3) . . ? O11 Gd1 O2 139.7(3) . . ? C2 C1 C6 118.8(13) . . ? C2 C1 C13 120.6(12) . . ? C6 C1 C13 120.6(12) . . ? C3 C2 C1 118.8(13) . . ? O9 C3 C4 118.9(12) . . ? O9 C3 C2 119.7(12) . . ? C4 C3 C2 121.4(12) . . ? C3 C4 C5 120.1(14) . . ? C6 C5 C4 118.3(13) . . ? C6 C5 C15 117.7(12) . . ? C4 C5 C15 123.9(13) . . ? C5 C6 C1 122.5(12) . . ? O9 C7 C8 121.8(12) . . ? O9 C7 C12 120.3(11) . . ? C8 C7 C12 117.8(11) . . ? C9 C8 C7 122.2(12) . . ? C9 C8 N1 116.9(12) . . ? C7 C8 N1 120.9(11) . . ? C8 C9 C10 120.3(12) . . ? C11 C10 C9 117.0(12) . . ? C11 C10 C14 123.0(12) . . ? C9 C10 C14 119.9(11) . . ? C10 C11 C12 123.7(14) . . ? C11 C12 C7 119.1(13) . . ? O2 C13 O1 121.8(13) . . ? O2 C13 C1 119.8(12) . . ? O1 C13 C1 118.4(12) . . ? O5 C14 O6 123.9(12) . . ? O5 C14 C10 119.9(11) . . ? O6 C14 C10 116.2(11) . . ? O7 C15 O8 124.6(12) . . ? O7 C15 C5 120.7(11) . . ? O8 C15 C5 114.7(12) . . ? O3 N1 O4 119.9(12) . . ? O3 N1 C8 121.4(11) . . ? O4 N1 C8 118.6(11) . . ? C13 O1 Gd1 93.2(8) . . ? C13 O2 Gd1 91.1(8) . . ? C14 O5 Gd1 161.0(9) . 4_566 ? C14 O6 Gd1 133.5(8) . 4_666 ? C15 O8 Gd1 143.1(9) . 3_667 ? C7 O9 C3 119.6(10) . . ? _diffrn_measured_fraction_theta_max 0.997 _diffrn_reflns_theta_full 26.07 _diffrn_measured_fraction_theta_full 0.997 _refine_diff_density_max 2.082 _refine_diff_density_min -3.746 _refine_diff_density_rms 0.359