# Electronic Supplementary Material (ESI) for Physical Chemistry Chemical Physics # This journal is © The Owner Societies 2012 ####################################################################### # # Cambridge Crystallographic Data Centre # CCDC # ####################################################################### # # This CIF contains data from an original supplementary publication # deposited with the CCDC, and may include chemical, crystal, # experimental, refinement, atomic coordinates, # anisotropic displacement parameters and molecular geometry data, # as required by the journal to which it was submitted. # # This CIF is provided on the understanding that it is used for bona # fide research purposes only. It may contain copyright material # of the CCDC or of third parties, and may not be copied or further # disseminated in any form, whether machine-readable or not, # except for the purpose of generating routine backup copies # on your local computer system. # # For further information on the CCDC, data deposition and # data retrieval see: # www.ccdc.cam.ac.uk # # Bona fide researchers may freely download Mercury and enCIFer # from this site to visualise CIF-encoded structures and # to carry out CIF format checking respectively. # ####################################################################### data_tr47 _database_code_depnum_ccdc_archive 'CCDC 866881' #TrackingRef 'C1_tr47.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C21 H26 N5 O14 Sm Zn' _chemical_formula_weight 788.17 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 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' Zn Zn 0.2839 1.4301 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Orthorhombic _symmetry_space_group_name_H-M P212121 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, -y, z+1/2' 'x+1/2, -y+1/2, -z' '-x, y+1/2, -z+1/2' _cell_length_a 8.8341(3) _cell_length_b 17.4965(7) _cell_length_c 17.9724(6) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 2777.92(17) _cell_formula_units_Z 4 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 45268 _cell_measurement_theta_min 2.26 _cell_measurement_theta_max 33.42 _exptl_crystal_description needle _exptl_crystal_colour yellow _exptl_crystal_size_max 0.5 _exptl_crystal_size_mid 0.07 _exptl_crystal_size_min 0.07 _exptl_crystal_density_meas 'not measured' _exptl_crystal_density_diffrn 1.880 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1556 _exptl_absorpt_coefficient_mu 3.034 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.5584 _exptl_absorpt_correction_T_max 0.6278 _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 293(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'STOE-IPDS II' _diffrn_measurement_method 'omega scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 44577 _diffrn_reflns_av_R_equivalents 0.0644 _diffrn_reflns_av_sigmaI/netI 0.0710 _diffrn_reflns_limit_h_min -12 _diffrn_reflns_limit_h_max 13 _diffrn_reflns_limit_k_min -27 _diffrn_reflns_limit_k_max 27 _diffrn_reflns_limit_l_min -27 _diffrn_reflns_limit_l_max 27 _diffrn_reflns_theta_min 2.55 _diffrn_reflns_theta_max 33.52 _reflns_number_total 10696 _reflns_number_gt 7994 _reflns_threshold_expression >2sigma(I) _computing_data_collection X-Area _computing_cell_refinement X-Area _computing_data_reduction X-Area _computing_structure_solution 'SHELXS-97 (Sheldrick, 1997)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics ? _computing_publication_material ? _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^)+(0.0177P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _refine_ls_abs_structure_Flack -0.024(9) _refine_ls_number_reflns 10696 _refine_ls_number_parameters 379 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0696 _refine_ls_R_factor_gt 0.0435 _refine_ls_wR_factor_ref 0.0573 _refine_ls_wR_factor_gt 0.0532 _refine_ls_goodness_of_fit_ref 0.956 _refine_ls_restrained_S_all 0.956 _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 C1 C 0.2244(6) 0.6728(3) 0.1790(3) 0.0695(15) Uani 1 1 d . . . H1A H 0.2822 0.6593 0.1358 0.104 Uiso 1 1 calc R . . H1B H 0.1304 0.6956 0.1639 0.104 Uiso 1 1 calc R . . H1C H 0.2043 0.6278 0.2079 0.104 Uiso 1 1 calc R . . C2 C 0.2418(3) 0.7520(2) 0.28841(19) 0.0358(6) Uani 1 1 d . . . C3 C 0.0964(5) 0.7356(2) 0.3101(2) 0.0441(8) Uani 1 1 d . . . H3 H 0.0351 0.7047 0.2807 0.053 Uiso 1 1 calc R . . C4 C 0.0421(5) 0.7652(3) 0.3762(2) 0.0535(11) Uani 1 1 d . . . H4 H -0.0567 0.7548 0.3909 0.064 Uiso 1 1 calc R . . C5 C 0.1328(5) 0.8099(2) 0.4200(2) 0.0480(10) Uani 1 1 d . . . H5 H 0.0953 0.8292 0.4645 0.058 Uiso 1 1 calc R . . C6 C 0.2815(5) 0.8269(2) 0.3986(2) 0.0362(8) Uani 1 1 d . . . C7 C 0.3385(4) 0.79780(19) 0.33180(19) 0.0302(8) Uani 1 1 d . . . C8 C 0.3680(5) 0.8738(2) 0.44881(19) 0.0386(9) Uani 1 1 d . . . H8 H 0.3235 0.8830 0.4948 0.046 Uiso 1 1 calc R . . C9 C 0.5544(5) 0.9528(3) 0.5006(2) 0.0505(11) Uani 1 1 d . . . H9A H 0.5059 0.9365 0.5463 0.061 Uiso 1 1 calc R . . H9B H 0.5244 1.0053 0.4914 0.061 Uiso 1 1 calc R . . C10 C 0.7248(5) 0.9503(2) 0.51152(19) 0.0375(9) Uani 1 1 d . . . C11 C 0.7590(6) 0.9931(3) 0.5846(2) 0.0576(12) Uani 1 1 d . . . H11A H 0.8661 0.9927 0.5937 0.086 Uiso 1 1 calc R . . H11B H 0.7077 0.9684 0.6251 0.086 Uiso 1 1 calc R . . H11C H 0.7246 1.0450 0.5807 0.086 Uiso 1 1 calc R . . C12 C 0.7831(6) 0.8686(2) 0.5184(2) 0.0494(11) Uani 1 1 d . . . H12A H 0.8907 0.8693 0.5259 0.074 Uiso 1 1 calc R . . H12B H 0.7601 0.8409 0.4736 0.074 Uiso 1 1 calc R . . H12C H 0.7352 0.8440 0.5599 0.074 Uiso 1 1 calc R . . C13 C 0.8060(6) 0.9935(2) 0.4506(2) 0.0532(12) Uani 1 1 d . . . H13A H 0.7583 1.0431 0.4446 0.064 Uiso 1 1 calc R . . H13B H 0.9099 1.0021 0.4659 0.064 Uiso 1 1 calc R . . C14 C 0.9278(5) 0.96020(19) 0.3396(2) 0.0398(9) Uani 1 1 d . . . H14 H 1.0053 0.9885 0.3613 0.048 Uiso 1 1 calc R . . C15 C 0.9589(4) 0.9283(2) 0.26662(19) 0.0354(8) Uani 1 1 d . . . C16 C 1.0884(5) 0.9550(2) 0.2301(2) 0.0517(10) Uani 1 1 d . . . H16 H 1.1479 0.9919 0.2531 0.062 Uiso 1 1 calc R . . C17 C 1.1302(5) 0.9281(2) 0.1612(3) 0.0557(12) Uani 1 1 d . . . H17 H 1.2161 0.9469 0.1376 0.067 Uiso 1 1 calc R . . C18 C 1.0419(5) 0.8722(2) 0.1274(2) 0.0459(10) Uani 1 1 d . . . H18 H 1.0689 0.8532 0.0809 0.055 Uiso 1 1 calc R . . C19 C 0.9149(5) 0.84530(18) 0.16260(18) 0.0349(8) Uani 1 1 d . . . C20 C 0.8694(4) 0.87218(17) 0.23256(16) 0.0276(7) Uani 1 1 d . . . C21 C 0.8502(6) 0.7636(3) 0.0593(2) 0.0617(13) Uani 1 1 d . . . H21A H 0.7747 0.7272 0.0446 0.092 Uiso 1 1 calc R . . H21B H 0.9479 0.7396 0.0592 0.092 Uiso 1 1 calc R . . H21C H 0.8503 0.8057 0.0251 0.092 Uiso 1 1 calc R . . N1 N 0.4978(4) 0.90437(18) 0.43861(16) 0.0364(7) Uani 1 1 d . . . N2 N 0.8063(4) 0.95378(16) 0.37746(16) 0.0372(7) Uani 1 1 d . . . N3 N 0.4663(4) 0.8429(2) 0.09417(17) 0.0429(8) Uani 1 1 d . . . N4 N 0.6349(4) 0.63268(17) 0.33543(19) 0.0425(9) Uani 1 1 d . . . N5 N 0.6964(4) 0.60043(19) 0.13399(18) 0.0435(8) Uani 1 1 d . . . O1 O 0.3083(3) 0.72637(13) 0.22298(14) 0.0399(6) Uani 1 1 d . . . O2 O 0.4798(3) 0.80961(13) 0.30866(12) 0.0308(6) Uani 1 1 d . . . O3 O 0.7459(3) 0.84203(12) 0.26358(12) 0.0284(5) Uani 1 1 d . . . O4 O 0.8167(3) 0.79133(15) 0.13348(14) 0.0451(7) Uani 1 1 d . . . O5 O 0.5032(4) 0.86847(14) 0.15753(14) 0.0441(7) Uani 1 1 d . . . O6 O 0.4864(4) 0.77179(15) 0.08617(14) 0.0572(9) Uani 1 1 d . . . O7 O 0.4180(5) 0.88396(16) 0.04544(15) 0.0671(10) Uani 1 1 d . . . O8 O 0.5269(3) 0.62736(13) 0.28673(18) 0.0451(6) Uani 1 1 d . . . O9 O 0.7190(4) 0.68939(16) 0.33025(16) 0.0517(8) Uani 1 1 d . . . O10 O 0.6475(4) 0.58433(17) 0.38376(18) 0.0687(10) Uani 1 1 d . . . O11 O 0.7825(4) 0.63534(16) 0.17925(17) 0.0522(8) Uani 1 1 d . . . O12 O 0.5659(4) 0.62821(17) 0.12562(18) 0.0589(9) Uani 1 1 d . . . O13 O 0.7362(4) 0.54352(17) 0.10116(19) 0.0691(10) Uani 1 1 d . . . O14 O 0.5186(4) 0.97581(14) 0.26637(15) 0.0562(9) Uani 1 1 d . . . Sm1 Sm 0.59682(2) 0.743268(8) 0.211757(8) 0.02886(4) Uani 1 1 d . . . Zn1 Zn 0.61529(6) 0.89897(2) 0.34053(2) 0.03041(9) Uani 1 1 d . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 C1 0.054(3) 0.069(3) 0.085(4) -0.039(3) -0.015(3) -0.015(3) C2 0.0323(17) 0.0340(15) 0.0412(14) 0.003(2) -0.0081(16) -0.0018(17) C3 0.0291(18) 0.0427(18) 0.060(2) 0.0023(15) -0.0102(19) -0.003(2) C4 0.0235(19) 0.069(3) 0.068(3) 0.004(2) 0.0047(19) -0.003(2) C5 0.031(3) 0.060(2) 0.053(2) 0.0002(18) 0.0110(19) 0.006(2) C6 0.027(2) 0.046(2) 0.0364(18) -0.0020(15) 0.0029(16) 0.0044(17) C7 0.028(2) 0.0307(17) 0.0323(17) 0.0014(13) -0.0039(15) -0.0005(15) C8 0.030(2) 0.059(2) 0.0267(15) -0.0062(15) 0.0053(15) 0.0109(18) C9 0.041(3) 0.067(3) 0.044(2) -0.0296(19) -0.004(2) 0.009(2) C10 0.044(2) 0.046(2) 0.0233(15) -0.0127(14) -0.0027(16) 0.0018(19) C11 0.051(3) 0.083(3) 0.039(2) -0.028(2) -0.007(2) 0.002(3) C12 0.059(3) 0.051(2) 0.038(2) 0.0000(17) -0.001(2) 0.010(2) C13 0.073(4) 0.050(2) 0.037(2) -0.0165(17) 0.000(2) -0.025(2) C14 0.039(3) 0.0404(18) 0.0398(18) 0.0009(14) -0.0048(18) -0.0191(18) C15 0.030(2) 0.0394(18) 0.0368(17) 0.0038(14) 0.0012(15) -0.0061(16) C16 0.034(2) 0.062(2) 0.059(2) 0.0028(18) 0.005(2) -0.017(2) C17 0.043(3) 0.062(3) 0.062(3) 0.012(2) 0.021(2) -0.009(2) C18 0.041(3) 0.056(2) 0.041(2) 0.0060(18) 0.0165(19) 0.010(2) C19 0.040(2) 0.0318(15) 0.0334(15) 0.0028(12) 0.0051(19) 0.0030(18) C20 0.026(2) 0.0283(14) 0.0288(14) 0.0046(11) 0.0027(13) 0.0034(14) C21 0.082(4) 0.067(3) 0.0356(17) -0.018(2) 0.0185(19) 0.002(3) N1 0.0304(19) 0.0486(18) 0.0301(14) -0.0125(13) 0.0020(13) 0.0042(15) N2 0.046(2) 0.0352(15) 0.0307(14) -0.0037(12) -0.0016(15) -0.0134(15) N3 0.047(2) 0.0473(19) 0.0344(16) -0.0006(14) -0.0075(15) -0.0022(17) N4 0.046(2) 0.0366(16) 0.0447(17) 0.0050(13) -0.0006(17) 0.0012(16) N5 0.048(2) 0.0405(18) 0.0422(17) -0.0043(14) 0.0022(17) 0.0083(18) O1 0.0363(14) 0.0419(14) 0.0416(14) -0.0111(11) -0.0086(12) -0.0054(11) O2 0.0262(14) 0.0354(13) 0.0307(12) -0.0058(9) 0.0056(10) -0.0067(11) O3 0.0258(14) 0.0303(11) 0.0290(11) -0.0062(9) 0.0031(10) -0.0062(10) O4 0.0546(19) 0.0490(15) 0.0315(12) -0.0132(11) 0.0168(13) -0.0054(14) O5 0.062(2) 0.0374(14) 0.0333(13) -0.0063(11) -0.0086(14) 0.0024(13) O6 0.090(3) 0.0419(16) 0.0393(14) -0.0082(11) -0.0225(15) 0.0004(15) O7 0.101(3) 0.0603(17) 0.0399(14) 0.0076(12) -0.0222(19) 0.011(2) O8 0.0446(16) 0.0375(12) 0.0534(15) 0.0040(14) -0.0129(16) -0.0066(11) O9 0.058(2) 0.0477(16) 0.0491(16) 0.0004(13) -0.0163(16) -0.0133(16) O10 0.079(3) 0.0620(19) 0.0654(19) 0.0320(16) -0.0067(19) 0.0020(17) O11 0.0469(19) 0.0472(16) 0.0624(19) -0.0062(13) -0.0088(16) 0.0071(14) O12 0.049(2) 0.0611(18) 0.0669(19) -0.0316(15) -0.0211(17) 0.0224(17) O13 0.078(3) 0.0508(18) 0.078(2) -0.0261(16) 0.003(2) 0.0227(18) O14 0.090(2) 0.0346(14) 0.0438(17) -0.0009(11) -0.0103(16) 0.0131(15) Sm1 0.03439(8) 0.02546(7) 0.02674(6) -0.00652(6) -0.00246(8) -0.00141(9) Zn1 0.0326(2) 0.03273(18) 0.02591(16) -0.00663(14) 0.00185(19) -0.0046(2) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag C1 O1 1.432(4) . ? C1 H1A 0.9600 . ? C1 H1B 0.9600 . ? C1 H1C 0.9600 . ? C2 C3 1.373(5) . ? C2 O1 1.389(4) . ? C2 C7 1.407(5) . ? C3 C4 1.382(6) . ? C3 H3 0.9300 . ? C4 C5 1.368(6) . ? C4 H4 0.9300 . ? C5 C6 1.401(6) . ? C5 H5 0.9300 . ? C6 C7 1.398(5) . ? C6 C8 1.438(5) . ? C7 O2 1.332(4) . ? C8 N1 1.279(5) . ? C8 H8 0.9300 . ? C9 N1 1.486(4) . ? C9 C10 1.519(6) . ? C9 H9A 0.9700 . ? C9 H9B 0.9700 . ? C10 C13 1.511(6) . ? C10 C12 1.526(5) . ? C10 C11 1.543(5) . ? C11 H11A 0.9600 . ? C11 H11B 0.9600 . ? C11 H11C 0.9600 . ? C12 H12A 0.9600 . ? C12 H12B 0.9600 . ? C12 H12C 0.9600 . ? C13 N2 1.487(4) . ? C13 H13A 0.9700 . ? C13 H13B 0.9700 . ? C14 N2 1.276(5) . ? C14 C15 1.452(5) . ? C14 H14 0.9300 . ? C15 C16 1.398(5) . ? C15 C20 1.402(5) . ? C16 C17 1.376(6) . ? C16 H16 0.9300 . ? C17 C18 1.389(6) . ? C17 H17 0.9300 . ? C18 C19 1.372(6) . ? C18 H18 0.9300 . ? C19 O4 1.385(5) . ? C19 C20 1.401(4) . ? C20 O3 1.334(4) . ? C21 O4 1.448(4) . ? C21 H21A 0.9600 . ? C21 H21B 0.9600 . ? C21 H21C 0.9600 . ? N1 Zn1 2.048(3) . ? N2 Zn1 2.051(3) . ? N3 O7 1.211(4) . ? N3 O6 1.265(4) . ? N3 O5 1.266(4) . ? N3 Sm1 2.972(3) . ? N4 O10 1.218(4) . ? N4 O9 1.243(4) . ? N4 O8 1.298(4) . ? N4 Sm1 2.966(3) . ? N5 O13 1.210(4) . ? N5 O12 1.260(5) . ? N5 O11 1.270(4) . ? N5 Sm1 2.995(3) . ? O1 Sm1 2.574(3) . ? O2 Zn1 2.051(2) . ? O2 Sm1 2.334(2) . ? O3 Zn1 2.058(2) . ? O3 Sm1 2.364(2) . ? O4 Sm1 2.542(3) . ? O5 Sm1 2.536(3) . ? O6 Sm1 2.509(3) . ? O8 Sm1 2.512(3) . ? O9 Sm1 2.567(3) . ? O11 Sm1 2.569(3) . ? O12 Sm1 2.554(3) . ? O14 Zn1 2.077(3) . ? 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 C1 H1A 109.5 . . ? O1 C1 H1B 109.5 . . ? H1A C1 H1B 109.5 . . ? O1 C1 H1C 109.5 . . ? H1A C1 H1C 109.5 . . ? H1B C1 H1C 109.5 . . ? C3 C2 O1 124.6(3) . . ? C3 C2 C7 122.0(3) . . ? O1 C2 C7 113.4(3) . . ? C2 C3 C4 119.4(4) . . ? C2 C3 H3 120.3 . . ? C4 C3 H3 120.3 . . ? C5 C4 C3 120.3(4) . . ? C5 C4 H4 119.8 . . ? C3 C4 H4 119.8 . . ? C4 C5 C6 120.9(4) . . ? C4 C5 H5 119.6 . . ? C6 C5 H5 119.6 . . ? C7 C6 C5 119.7(4) . . ? C7 C6 C8 123.8(4) . . ? C5 C6 C8 116.6(3) . . ? O2 C7 C6 123.3(3) . . ? O2 C7 C2 119.0(3) . . ? C6 C7 C2 117.7(3) . . ? N1 C8 C6 128.7(3) . . ? N1 C8 H8 115.7 . . ? C6 C8 H8 115.7 . . ? N1 C9 C10 114.5(3) . . ? N1 C9 H9A 108.6 . . ? C10 C9 H9A 108.6 . . ? N1 C9 H9B 108.6 . . ? C10 C9 H9B 108.6 . . ? H9A C9 H9B 107.6 . . ? C13 C10 C9 111.2(4) . . ? C13 C10 C12 111.6(4) . . ? C9 C10 C12 111.8(4) . . ? C13 C10 C11 106.3(3) . . ? C9 C10 C11 106.9(3) . . ? C12 C10 C11 108.7(3) . . ? C10 C11 H11A 109.5 . . ? C10 C11 H11B 109.5 . . ? H11A C11 H11B 109.5 . . ? C10 C11 H11C 109.5 . . ? H11A C11 H11C 109.5 . . ? H11B C11 H11C 109.5 . . ? C10 C12 H12A 109.5 . . ? C10 C12 H12B 109.5 . . ? H12A C12 H12B 109.5 . . ? C10 C12 H12C 109.5 . . ? H12A C12 H12C 109.5 . . ? H12B C12 H12C 109.5 . . ? N2 C13 C10 114.0(3) . . ? N2 C13 H13A 108.7 . . ? C10 C13 H13A 108.7 . . ? N2 C13 H13B 108.7 . . ? C10 C13 H13B 108.7 . . ? H13A C13 H13B 107.6 . . ? N2 C14 C15 127.4(3) . . ? N2 C14 H14 116.3 . . ? C15 C14 H14 116.3 . . ? C16 C15 C20 119.3(3) . . ? C16 C15 C14 116.8(3) . . ? C20 C15 C14 123.9(3) . . ? C17 C16 C15 121.9(4) . . ? C17 C16 H16 119.1 . . ? C15 C16 H16 119.1 . . ? C16 C17 C18 118.9(4) . . ? C16 C17 H17 120.5 . . ? C18 C17 H17 120.5 . . ? C19 C18 C17 119.9(4) . . ? C19 C18 H18 120.0 . . ? C17 C18 H18 120.0 . . ? C18 C19 O4 124.9(3) . . ? C18 C19 C20 122.2(4) . . ? O4 C19 C20 112.8(3) . . ? O3 C20 C19 118.5(3) . . ? O3 C20 C15 123.8(3) . . ? C19 C20 C15 117.7(3) . . ? O4 C21 H21A 109.5 . . ? O4 C21 H21B 109.5 . . ? H21A C21 H21B 109.5 . . ? O4 C21 H21C 109.5 . . ? H21A C21 H21C 109.5 . . ? H21B C21 H21C 109.5 . . ? C8 N1 C9 115.7(3) . . ? C8 N1 Zn1 124.0(2) . . ? C9 N1 Zn1 120.0(3) . . ? C14 N2 C13 115.6(3) . . ? C14 N2 Zn1 124.1(2) . . ? C13 N2 Zn1 120.2(3) . . ? O7 N3 O6 123.5(3) . . ? O7 N3 O5 122.1(3) . . ? O6 N3 O5 114.4(3) . . ? O7 N3 Sm1 177.8(3) . . ? O6 N3 Sm1 56.60(17) . . ? O5 N3 Sm1 57.86(18) . . ? O10 N4 O9 123.6(4) . . ? O10 N4 O8 119.9(3) . . ? O9 N4 O8 116.5(3) . . ? O10 N4 Sm1 176.6(3) . . ? O9 N4 Sm1 59.40(19) . . ? O8 N4 Sm1 57.18(16) . . ? O13 N5 O12 121.7(4) . . ? O13 N5 O11 122.3(4) . . ? O12 N5 O11 116.0(3) . . ? O13 N5 Sm1 178.6(3) . . ? O12 N5 Sm1 57.67(18) . . ? O11 N5 Sm1 58.39(18) . . ? C2 O1 C1 117.4(3) . . ? C2 O1 Sm1 116.60(18) . . ? C1 O1 Sm1 123.0(3) . . ? C7 O2 Zn1 125.3(2) . . ? C7 O2 Sm1 124.8(2) . . ? Zn1 O2 Sm1 109.21(11) . . ? C20 O3 Zn1 123.22(19) . . ? C20 O3 Sm1 125.45(19) . . ? Zn1 O3 Sm1 107.85(10) . . ? C19 O4 C21 116.6(3) . . ? C19 O4 Sm1 119.68(19) . . ? C21 O4 Sm1 123.7(2) . . ? N3 O5 Sm1 97.1(2) . . ? N3 O6 Sm1 98.5(2) . . ? N4 O8 Sm1 97.08(19) . . ? N4 O9 Sm1 96.0(2) . . ? N5 O11 Sm1 96.7(2) . . ? N5 O12 Sm1 97.7(2) . . ? O2 Sm1 O3 65.74(8) . . ? O2 Sm1 O6 113.59(10) . . ? O3 Sm1 O6 115.19(9) . . ? O2 Sm1 O8 83.82(9) . . ? O3 Sm1 O8 121.05(8) . . ? O6 Sm1 O8 123.20(10) . . ? O2 Sm1 O5 73.31(9) . . ? O3 Sm1 O5 72.65(9) . . ? O6 Sm1 O5 49.89(8) . . ? O8 Sm1 O5 145.40(10) . . ? O2 Sm1 O4 125.94(8) . . ? O3 Sm1 O4 63.29(8) . . ? O6 Sm1 O4 74.53(10) . . ? O8 Sm1 O4 138.76(9) . . ? O5 Sm1 O4 75.57(10) . . ? O2 Sm1 O12 142.82(10) . . ? O3 Sm1 O12 150.99(10) . . ? O6 Sm1 O12 64.53(9) . . ? O8 Sm1 O12 70.28(10) . . ? O5 Sm1 O12 114.39(9) . . ? O4 Sm1 O12 90.40(10) . . ? O2 Sm1 O9 75.51(10) . . ? O3 Sm1 O9 72.98(8) . . ? O6 Sm1 O9 169.38(9) . . ? O8 Sm1 O9 50.35(9) . . ? O5 Sm1 O9 140.64(8) . . ? O4 Sm1 O9 105.03(10) . . ? O12 Sm1 O9 104.97(10) . . ? O2 Sm1 O11 144.89(9) . . ? O3 Sm1 O11 105.75(9) . . ? O6 Sm1 O11 100.94(10) . . ? O8 Sm1 O11 71.67(10) . . ? O5 Sm1 O11 139.10(9) . . ? O4 Sm1 O11 68.24(9) . . ? O12 Sm1 O11 49.53(9) . . ? O9 Sm1 O11 69.53(10) . . ? O2 Sm1 O1 63.90(8) . . ? O3 Sm1 O1 127.21(7) . . ? O6 Sm1 O1 73.05(10) . . ? O8 Sm1 O1 67.78(8) . . ? O5 Sm1 O1 78.83(9) . . ? O4 Sm1 O1 146.95(9) . . ? O12 Sm1 O1 81.44(9) . . ? O9 Sm1 O1 108.01(9) . . ? O11 Sm1 O1 124.46(9) . . ? O2 Sm1 N4 79.37(9) . . ? O3 Sm1 N4 96.81(9) . . ? O6 Sm1 N4 147.99(9) . . ? O8 Sm1 N4 25.74(9) . . ? O5 Sm1 N4 152.67(9) . . ? O4 Sm1 N4 122.96(10) . . ? O12 Sm1 N4 87.26(10) . . ? O9 Sm1 N4 24.64(9) . . ? O11 Sm1 N4 67.57(9) . . ? O1 Sm1 N4 88.77(9) . . ? O2 Sm1 N3 93.85(9) . . ? O3 Sm1 N3 93.88(9) . . ? O6 Sm1 N3 24.89(8) . . ? O8 Sm1 N3 139.41(9) . . ? O5 Sm1 N3 25.01(8) . . ? O4 Sm1 N3 73.08(10) . . ? O12 Sm1 N3 89.41(10) . . ? O9 Sm1 N3 165.57(9) . . ? O11 Sm1 N3 121.14(9) . . ? O1 Sm1 N3 74.86(9) . . ? N4 Sm1 N3 163.61(10) . . ? N1 Zn1 O2 88.83(11) . . ? N1 Zn1 N2 96.71(12) . . ? O2 Zn1 N2 157.98(12) . . ? N1 Zn1 O3 152.24(11) . . ? O2 Zn1 O3 76.73(9) . . ? N2 Zn1 O3 89.02(11) . . ? N1 Zn1 O14 108.31(13) . . ? O2 Zn1 O14 94.26(11) . . ? N2 Zn1 O14 104.07(13) . . ? O3 Zn1 O14 96.46(10) . . ? N1 Zn1 Sm1 124.66(9) . . ? O2 Zn1 Sm1 38.03(7) . . ? N2 Zn1 Sm1 127.07(9) . . ? O3 Zn1 Sm1 38.96(6) . . ? O14 Zn1 Sm1 93.38(7) . . ? _diffrn_measured_fraction_theta_max 0.986 _diffrn_reflns_theta_full 33.52 _diffrn_measured_fraction_theta_full 0.986 _refine_diff_density_max 0.645 _refine_diff_density_min -1.346 _refine_diff_density_rms 0.102 data_shelxl _database_code_depnum_ccdc_archive 'CCDC 866882' #TrackingRef 'C2b_tr45b.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C21 H28 N5 O15 Tb Zn' _chemical_formula_weight 814.76 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Tb Tb -0.1723 4.1537 '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' Zn Zn 0.2839 1.4301 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Triclinic _symmetry_space_group_name_H-M P-1 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 8.8950(7) _cell_length_b 13.2908(11) _cell_length_c 13.3864(10) _cell_angle_alpha 83.147(6) _cell_angle_beta 71.607(6) _cell_angle_gamma 73.388(6) _cell_volume 1438.3(2) _cell_formula_units_Z 2 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 20756 _cell_measurement_theta_min 3.20 _cell_measurement_theta_max 33.36 _exptl_crystal_description prism _exptl_crystal_colour colorless _exptl_crystal_size_max 0.5 _exptl_crystal_size_mid 0.3 _exptl_crystal_size_min 0.2 _exptl_crystal_density_meas 'not measured' _exptl_crystal_density_diffrn 1.877 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 804 _exptl_absorpt_coefficient_mu 3.352 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.2097 _exptl_absorpt_correction_T_max 0.4218 _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 293(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'STOE IPDS II' _diffrn_measurement_method 'omega scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 23974 _diffrn_reflns_av_R_equivalents 0.0468 _diffrn_reflns_av_sigmaI/netI 0.0555 _diffrn_reflns_limit_h_min -13 _diffrn_reflns_limit_h_max 13 _diffrn_reflns_limit_k_min -20 _diffrn_reflns_limit_k_max 20 _diffrn_reflns_limit_l_min -20 _diffrn_reflns_limit_l_max 20 _diffrn_reflns_theta_min 3.20 _diffrn_reflns_theta_max 33.36 _reflns_number_total 10918 _reflns_number_gt 8339 _reflns_threshold_expression >2sigma(I) _computing_data_collection X-Area _computing_cell_refinement X-Area _computing_data_reduction X-Area _computing_structure_solution 'SHELXS-97 (Sheldrick, 1997)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics ? _computing_publication_material ? _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^+0.0000P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment mixed _refine_ls_extinction_method SHELXL _refine_ls_extinction_coef 0.0209(6) _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_number_reflns 10918 _refine_ls_number_parameters 397 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0585 _refine_ls_R_factor_gt 0.0379 _refine_ls_wR_factor_ref 0.0819 _refine_ls_wR_factor_gt 0.0761 _refine_ls_goodness_of_fit_ref 0.957 _refine_ls_restrained_S_all 0.957 _refine_ls_shift/su_max 0.003 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group C1 C 0.4081(5) 0.9983(3) 0.3873(3) 0.0527(9) Uani 1 1 d . . . H1A H 0.4154 0.9518 0.4472 0.079 Uiso 1 1 calc R . . H1B H 0.3330 1.0648 0.4105 0.079 Uiso 1 1 calc R . . H1C H 0.5146 1.0082 0.3499 0.079 Uiso 1 1 calc R . . C2 C 0.3323(4) 1.0116(2) 0.2287(2) 0.0341(6) Uani 1 1 d . . . C3 C 0.3523(4) 1.1107(3) 0.2035(3) 0.0431(7) Uani 1 1 d . . . H3 H 0.3761 1.1457 0.2503 0.052 Uiso 1 1 calc R . . C4 C 0.3370(5) 1.1594(3) 0.1073(3) 0.0463(8) Uani 1 1 d . . . H4 H 0.3492 1.2271 0.0904 0.056 Uiso 1 1 calc R . . C5 C 0.3040(4) 1.1067(2) 0.0382(3) 0.0401(7) Uani 1 1 d . . . H5 H 0.2980 1.1384 -0.0268 0.048 Uiso 1 1 calc R . . C6 C 0.2789(4) 1.0054(2) 0.0636(2) 0.0324(6) Uani 1 1 d . . . C7 C 0.2893(4) 0.9583(2) 0.1616(2) 0.0304(5) Uani 1 1 d . . . C8 C 0.2535(4) 0.9547(2) -0.0174(2) 0.0344(6) Uani 1 1 d . . . H8 H 0.2641 0.9904 -0.0823 0.041 Uiso 1 1 calc R . . C9 C 0.1941(5) 0.8388(3) -0.1077(2) 0.0450(8) Uani 1 1 d . . . H9A H 0.2672 0.8657 -0.1683 0.054 Uiso 1 1 calc R . . H9B H 0.0824 0.8740 -0.1080 0.054 Uiso 1 1 calc R . . C11 C 0.1961(7) 0.7113(4) -0.2260(3) 0.0678(13) Uani 1 1 d . . . H11A H 0.2116 0.6385 -0.2370 0.102 Uiso 1 1 calc R . . H11B H 0.2731 0.7388 -0.2822 0.102 Uiso 1 1 calc R . . H11C H 0.0863 0.7498 -0.2247 0.102 Uiso 1 1 calc R . . C12 C 0.3993(5) 0.6609(3) -0.1222(3) 0.0555(10) Uani 1 1 d . . . H12A H 0.4138 0.5876 -0.1301 0.083 Uiso 1 1 calc R . . H12B H 0.4174 0.6705 -0.0574 0.083 Uiso 1 1 calc R . . H12C H 0.4764 0.6864 -0.1802 0.083 Uiso 1 1 calc R . . C13 C 0.0971(4) 0.6766(3) -0.0360(2) 0.0389(7) Uani 1 1 d . . . H13A H -0.0110 0.7245 -0.0275 0.047 Uiso 1 1 calc R . . H13B H 0.0960 0.6107 -0.0596 0.047 Uiso 1 1 calc R . . C14 C 0.1297(4) 0.5672(2) 0.1107(2) 0.0359(6) Uani 1 1 d . . . H14 H 0.1096 0.5198 0.0740 0.043 Uiso 1 1 calc R . . C15 C 0.1579(4) 0.5295(2) 0.2111(2) 0.0345(6) Uani 1 1 d . . . C16 C 0.1388(5) 0.4282(3) 0.2474(3) 0.0463(8) Uani 1 1 d . . . H16 H 0.1082 0.3898 0.2070 0.056 Uiso 1 1 calc R . . C17 C 0.1641(5) 0.3857(3) 0.3403(3) 0.0514(9) Uani 1 1 d . . . H17 H 0.1499 0.3193 0.3631 0.062 Uiso 1 1 calc R . . C18 C 0.2114(5) 0.4418(3) 0.4010(3) 0.0465(8) Uani 1 1 d . . . H18 H 0.2286 0.4130 0.4646 0.056 Uiso 1 1 calc R . . C19 C 0.2326(4) 0.5401(2) 0.3668(2) 0.0364(6) Uani 1 1 d . . . C20 C 0.2071(4) 0.5860(2) 0.2712(2) 0.0313(5) Uani 1 1 d . . . C021 C 0.2235(4) 0.7222(3) -0.1207(2) 0.0405(7) Uani 1 1 d . . . C21 C 0.2822(6) 0.5693(4) 0.5261(3) 0.0537(9) Uani 1 1 d . . . H21A H 0.3168 0.6183 0.5553 0.081 Uiso 1 1 calc R . . H21B H 0.3570 0.5009 0.5255 0.081 Uiso 1 1 calc R . . H21C H 0.1738 0.5664 0.5680 0.081 Uiso 1 1 calc R . . Tb1 Tb 0.369821(18) 0.756424(11) 0.317976(10) 0.02859(5) Uani 1 1 d . . . N1 N 0.2183(3) 0.8671(2) -0.01070(19) 0.0329(5) Uani 1 1 d . . . N2 N 0.1293(3) 0.6580(2) 0.06704(19) 0.0342(5) Uani 1 1 d . . . N3 N 0.0939(4) 0.8459(3) 0.4995(2) 0.0488(7) Uani 1 1 d . . . N4 N 0.6417(4) 0.6288(3) 0.1607(3) 0.0553(8) Uani 1 1 d . . . N5 N 0.6704(4) 0.7408(3) 0.3760(3) 0.0574(9) Uani 1 1 d . . . O1 O 0.3503(3) 0.95349(18) 0.31898(18) 0.0406(5) Uani 1 1 d . . . O2 O 0.2648(3) 0.86425(16) 0.19316(17) 0.0351(4) Uani 1 1 d . . . O3 O 0.2322(3) 0.68093(16) 0.24227(16) 0.0346(4) Uani 1 1 d . . . O4 O 0.2809(3) 0.60294(19) 0.42014(17) 0.0418(5) Uani 1 1 d . . . O5 O 0.2388(3) 0.8165(2) 0.50278(19) 0.0500(6) Uani 1 1 d . . . O6 O 0.0721(3) 0.8329(2) 0.4139(2) 0.0518(6) Uani 1 1 d . . . O7 O -0.0192(4) 0.8855(4) 0.5743(3) 0.0900(13) Uani 1 1 d . . . O8 O 0.5878(4) 0.5952(2) 0.2539(2) 0.0549(7) Uani 1 1 d . . . O9 O 0.5618(4) 0.7167(2) 0.1354(2) 0.0567(7) Uani 1 1 d . . . O10 O 0.7658(5) 0.5772(3) 0.0999(3) 0.0953(14) Uani 1 1 d . . . O11 O 0.6502(3) 0.7867(2) 0.2905(2) 0.0473(6) Uani 1 1 d . . . O12 O 0.5532(3) 0.7078(3) 0.4360(2) 0.0593(8) Uani 1 1 d . . . O13 O 0.7978(5) 0.7306(5) 0.3955(4) 0.122(2) Uani 1 1 d . . . O14 O -0.0798(3) 0.8652(2) 0.1852(2) 0.0414(5) Uani 1 1 d . . . O15 O -0.1597(5) 0.9971(3) 0.3409(3) 0.0773(10) Uani 1 1 d . . . Zn1 Zn 0.16112(4) 0.78104(3) 0.12808(2) 0.03091(7) Uani 1 1 d . . . H1W H -0.147(6) 0.832(4) 0.214(4) 0.051(13) Uiso 1 1 d . . . H2W H -0.097(5) 0.906(4) 0.232(4) 0.047(11) Uiso 1 1 d . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 C1 0.062(2) 0.057(2) 0.056(2) -0.0122(17) -0.0310(18) -0.0204(19) C2 0.0311(14) 0.0318(14) 0.0415(14) -0.0069(11) -0.0116(11) -0.0082(11) C3 0.0438(18) 0.0308(15) 0.058(2) -0.0088(13) -0.0140(15) -0.0126(13) C4 0.049(2) 0.0268(14) 0.063(2) 0.0003(14) -0.0119(16) -0.0154(14) C5 0.0392(17) 0.0300(14) 0.0482(17) 0.0037(12) -0.0089(13) -0.0113(12) C6 0.0309(14) 0.0278(13) 0.0377(14) 0.0013(10) -0.0083(11) -0.0096(11) C7 0.0295(13) 0.0241(12) 0.0380(13) -0.0027(10) -0.0095(11) -0.0075(10) C8 0.0332(14) 0.0337(14) 0.0340(13) 0.0040(11) -0.0098(11) -0.0076(11) C9 0.062(2) 0.0500(19) 0.0313(14) 0.0025(13) -0.0204(14) -0.0221(17) C11 0.099(4) 0.089(3) 0.0350(17) -0.0053(18) -0.025(2) -0.048(3) C12 0.044(2) 0.060(2) 0.059(2) -0.0204(18) -0.0031(17) -0.0150(18) C13 0.0400(16) 0.0479(18) 0.0351(14) -0.0036(12) -0.0149(12) -0.0161(14) C14 0.0376(16) 0.0352(15) 0.0396(14) -0.0094(11) -0.0108(12) -0.0143(12) C15 0.0360(15) 0.0313(14) 0.0388(14) -0.0030(11) -0.0084(12) -0.0148(12) C16 0.048(2) 0.0338(16) 0.061(2) -0.0038(14) -0.0144(16) -0.0189(14) C17 0.058(2) 0.0328(16) 0.064(2) 0.0099(15) -0.0155(18) -0.0214(16) C18 0.054(2) 0.0377(17) 0.0497(18) 0.0126(14) -0.0169(16) -0.0187(15) C19 0.0397(16) 0.0337(14) 0.0368(14) 0.0025(11) -0.0096(12) -0.0144(12) C20 0.0332(14) 0.0279(13) 0.0340(13) -0.0005(10) -0.0092(11) -0.0109(11) C021 0.0496(19) 0.0510(19) 0.0278(13) -0.0065(12) -0.0114(12) -0.0216(15) C21 0.068(3) 0.068(3) 0.0321(15) 0.0127(15) -0.0203(16) -0.029(2) Tb1 0.03233(8) 0.02889(7) 0.02667(6) -0.00107(4) -0.01103(5) -0.00865(5) N1 0.0365(13) 0.0349(12) 0.0288(10) 0.0000(9) -0.0096(9) -0.0121(10) N2 0.0381(13) 0.0368(13) 0.0321(11) -0.0050(9) -0.0115(10) -0.0136(11) N3 0.0477(17) 0.0523(18) 0.0402(14) -0.0125(13) -0.0053(12) -0.0079(14) N4 0.0499(19) 0.0501(19) 0.0592(19) -0.0208(15) 0.0023(15) -0.0156(15) N5 0.0482(18) 0.061(2) 0.073(2) 0.0250(17) -0.0324(17) -0.0233(16) O1 0.0498(13) 0.0360(11) 0.0455(12) -0.0073(9) -0.0240(10) -0.0125(10) O2 0.0508(13) 0.0263(9) 0.0388(10) 0.0022(8) -0.0234(9) -0.0165(9) O3 0.0513(13) 0.0294(10) 0.0320(9) 0.0039(7) -0.0191(9) -0.0186(9) O4 0.0586(15) 0.0419(12) 0.0322(10) 0.0084(9) -0.0194(10) -0.0218(11) O5 0.0486(15) 0.0644(17) 0.0376(12) -0.0106(11) -0.0162(10) -0.0084(12) O6 0.0415(14) 0.0668(18) 0.0487(14) -0.0140(12) -0.0160(11) -0.0088(12) O7 0.062(2) 0.124(3) 0.063(2) -0.045(2) 0.0060(16) -0.003(2) O8 0.0524(16) 0.0375(13) 0.0667(17) -0.0007(12) -0.0099(13) -0.0081(12) O9 0.0645(18) 0.0586(17) 0.0395(13) -0.0022(11) -0.0042(12) -0.0168(14) O10 0.068(2) 0.085(3) 0.102(3) -0.048(2) 0.026(2) -0.0132(19) O11 0.0451(14) 0.0477(14) 0.0542(14) 0.0129(11) -0.0199(11) -0.0201(11) O12 0.0448(15) 0.084(2) 0.0582(16) 0.0250(15) -0.0252(13) -0.0305(15) O13 0.074(2) 0.188(5) 0.136(4) 0.096(4) -0.076(3) -0.076(3) O14 0.0387(13) 0.0437(13) 0.0410(12) -0.0043(10) -0.0080(10) -0.0125(11) O15 0.092(3) 0.071(2) 0.072(2) -0.0239(17) -0.0426(19) 0.0019(19) Zn1 0.03907(18) 0.02934(16) 0.02914(14) -0.00047(11) -0.01320(13) -0.01314(13) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag C1 O1 1.434(4) . ? C1 H1A 0.9600 . ? C1 H1B 0.9600 . ? C1 H1C 0.9600 . ? C2 C3 1.367(5) . ? C2 O1 1.382(4) . ? C2 C7 1.407(4) . ? C3 C4 1.399(6) . ? C3 H3 0.9300 . ? C4 C5 1.370(5) . ? C4 H4 0.9300 . ? C5 C6 1.412(4) . ? C5 H5 0.9300 . ? C6 C7 1.403(4) . ? C6 C8 1.448(4) . ? C7 O2 1.327(3) . ? C8 N1 1.275(4) . ? C8 H8 0.9300 . ? C9 N1 1.488(4) . ? C9 C021 1.518(5) . ? C9 H9A 0.9700 . ? C9 H9B 0.9700 . ? C11 C021 1.534(5) . ? C11 H11A 0.9600 . ? C11 H11B 0.9600 . ? C11 H11C 0.9600 . ? C12 C021 1.537(6) . ? C12 H12A 0.9600 . ? C12 H12B 0.9600 . ? C12 H12C 0.9600 . ? C13 N2 1.474(4) . ? C13 C021 1.530(5) . ? C13 H13A 0.9700 . ? C13 H13B 0.9700 . ? C14 N2 1.276(4) . ? C14 C15 1.449(5) . ? C14 H14 0.9300 . ? C15 C20 1.398(4) . ? C15 C16 1.415(5) . ? C16 C17 1.361(6) . ? C16 H16 0.9300 . ? C17 C18 1.390(6) . ? C17 H17 0.9300 . ? C18 C19 1.377(5) . ? C18 H18 0.9300 . ? C19 O4 1.390(4) . ? C19 C20 1.407(4) . ? C20 O3 1.335(3) . ? C21 O4 1.437(4) . ? C21 H21A 0.9600 . ? C21 H21B 0.9600 . ? C21 H21C 0.9600 . ? Tb1 O3 2.293(2) . ? Tb1 O2 2.317(2) . ? Tb1 O8 2.470(3) . ? Tb1 O4 2.496(2) . ? Tb1 O5 2.497(2) . ? Tb1 O6 2.514(3) . ? Tb1 O9 2.515(3) . ? Tb1 O12 2.521(3) . ? Tb1 O11 2.545(3) . ? Tb1 O1 2.576(2) . ? Tb1 N4 2.907(3) . ? Tb1 N3 2.933(3) . ? N1 Zn1 2.061(2) . ? N2 Zn1 2.037(3) . ? N3 O7 1.216(4) . ? N3 O5 1.249(4) . ? N3 O6 1.261(4) . ? N4 O10 1.219(4) . ? N4 O9 1.252(5) . ? N4 O8 1.264(5) . ? N5 O13 1.209(5) . ? N5 O12 1.255(4) . ? N5 O11 1.271(4) . ? O2 Zn1 2.038(2) . ? O3 Zn1 2.037(2) . ? O14 Zn1 2.056(3) . ? O14 H1W 0.82(5) . ? O14 H2W 0.83(5) . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag O1 C1 H1A 109.5 . . ? O1 C1 H1B 109.5 . . ? H1A C1 H1B 109.5 . . ? O1 C1 H1C 109.5 . . ? H1A C1 H1C 109.5 . . ? H1B C1 H1C 109.5 . . ? C3 C2 O1 125.8(3) . . ? C3 C2 C7 121.3(3) . . ? O1 C2 C7 112.9(3) . . ? C2 C3 C4 120.1(3) . . ? C2 C3 H3 119.9 . . ? C4 C3 H3 119.9 . . ? C5 C4 C3 119.6(3) . . ? C5 C4 H4 120.2 . . ? C3 C4 H4 120.2 . . ? C4 C5 C6 121.3(3) . . ? C4 C5 H5 119.3 . . ? C6 C5 H5 119.3 . . ? C7 C6 C5 118.8(3) . . ? C7 C6 C8 124.4(3) . . ? C5 C6 C8 116.7(3) . . ? O2 C7 C6 123.1(3) . . ? O2 C7 C2 118.1(3) . . ? C6 C7 C2 118.8(3) . . ? N1 C8 C6 128.1(3) . . ? N1 C8 H8 116.0 . . ? C6 C8 H8 116.0 . . ? N1 C9 C021 115.5(3) . . ? N1 C9 H9A 108.4 . . ? C021 C9 H9A 108.4 . . ? N1 C9 H9B 108.4 . . ? C021 C9 H9B 108.4 . . ? H9A C9 H9B 107.5 . . ? C021 C11 H11A 109.5 . . ? C021 C11 H11B 109.5 . . ? H11A C11 H11B 109.5 . . ? C021 C11 H11C 109.5 . . ? H11A C11 H11C 109.5 . . ? H11B C11 H11C 109.5 . . ? C021 C12 H12A 109.5 . . ? C021 C12 H12B 109.5 . . ? H12A C12 H12B 109.5 . . ? C021 C12 H12C 109.5 . . ? H12A C12 H12C 109.5 . . ? H12B C12 H12C 109.5 . . ? N2 C13 C021 113.5(3) . . ? N2 C13 H13A 108.9 . . ? C021 C13 H13A 108.9 . . ? N2 C13 H13B 108.9 . . ? C021 C13 H13B 108.9 . . ? H13A C13 H13B 107.7 . . ? N2 C14 C15 127.4(3) . . ? N2 C14 H14 116.3 . . ? C15 C14 H14 116.3 . . ? C20 C15 C16 119.1(3) . . ? C20 C15 C14 123.8(3) . . ? C16 C15 C14 117.1(3) . . ? C17 C16 C15 121.4(3) . . ? C17 C16 H16 119.3 . . ? C15 C16 H16 119.3 . . ? C16 C17 C18 119.9(3) . . ? C16 C17 H17 120.0 . . ? C18 C17 H17 120.0 . . ? C19 C18 C17 119.8(3) . . ? C19 C18 H18 120.1 . . ? C17 C18 H18 120.1 . . ? C18 C19 O4 124.9(3) . . ? C18 C19 C20 121.5(3) . . ? O4 C19 C20 113.6(3) . . ? O3 C20 C15 123.5(3) . . ? O3 C20 C19 118.2(3) . . ? C15 C20 C19 118.3(3) . . ? C9 C021 C13 111.7(3) . . ? C9 C021 C11 106.6(3) . . ? C13 C021 C11 106.1(3) . . ? C9 C021 C12 111.5(3) . . ? C13 C021 C12 110.9(3) . . ? C11 C021 C12 109.8(3) . . ? O4 C21 H21A 109.5 . . ? O4 C21 H21B 109.5 . . ? H21A C21 H21B 109.5 . . ? O4 C21 H21C 109.5 . . ? H21A C21 H21C 109.5 . . ? H21B C21 H21C 109.5 . . ? O3 Tb1 O2 66.29(7) . . ? O3 Tb1 O8 80.72(9) . . ? O2 Tb1 O8 116.71(9) . . ? O3 Tb1 O4 65.46(7) . . ? O2 Tb1 O4 128.42(8) . . ? O8 Tb1 O4 71.77(9) . . ? O3 Tb1 O5 119.30(9) . . ? O2 Tb1 O5 114.98(8) . . ? O8 Tb1 O5 128.28(10) . . ? O4 Tb1 O5 75.28(9) . . ? O3 Tb1 O6 75.96(9) . . ? O2 Tb1 O6 75.44(9) . . ? O8 Tb1 O6 146.15(10) . . ? O4 Tb1 O6 76.34(9) . . ? O5 Tb1 O6 50.26(8) . . ? O3 Tb1 O9 76.32(9) . . ? O2 Tb1 O9 69.10(9) . . ? O8 Tb1 O9 50.87(10) . . ? O4 Tb1 O9 114.84(9) . . ? O5 Tb1 O9 164.37(10) . . ? O6 Tb1 O9 141.43(10) . . ? O3 Tb1 O12 140.08(9) . . ? O2 Tb1 O12 152.42(9) . . ? O8 Tb1 O12 71.04(11) . . ? O4 Tb1 O12 78.98(9) . . ? O5 Tb1 O12 64.29(10) . . ? O6 Tb1 O12 113.75(9) . . ? O9 Tb1 O12 104.73(10) . . ? O3 Tb1 O11 142.01(9) . . ? O2 Tb1 O11 105.49(8) . . ? O8 Tb1 O11 70.14(10) . . ? O4 Tb1 O11 123.64(8) . . ? O5 Tb1 O11 98.09(9) . . ? O6 Tb1 O11 140.16(9) . . ? O9 Tb1 O11 66.52(10) . . ? O12 Tb1 O11 50.13(8) . . ? O3 Tb1 O1 127.10(7) . . ? O2 Tb1 O1 63.21(7) . . ? O8 Tb1 O1 136.55(9) . . ? O4 Tb1 O1 146.01(8) . . ? O5 Tb1 O1 71.44(9) . . ? O6 Tb1 O1 77.27(9) . . ? O9 Tb1 O1 99.15(9) . . ? O12 Tb1 O1 92.55(9) . . ? O11 Tb1 O1 68.72(8) . . ? O3 Tb1 N4 78.98(9) . . ? O2 Tb1 N4 93.44(10) . . ? O8 Tb1 N4 25.58(10) . . ? O4 Tb1 N4 94.37(9) . . ? O5 Tb1 N4 150.26(10) . . ? O6 Tb1 N4 154.91(10) . . ? O9 Tb1 N4 25.40(10) . . ? O12 Tb1 N4 86.55(11) . . ? O11 Tb1 N4 64.15(10) . . ? O1 Tb1 N4 118.14(9) . . ? O3 Tb1 N3 98.15(9) . . ? O2 Tb1 N3 95.33(9) . . ? O8 Tb1 N3 143.46(10) . . ? O4 Tb1 N3 74.65(9) . . ? O5 Tb1 N3 24.97(9) . . ? O6 Tb1 N3 25.30(9) . . ? O9 Tb1 N3 164.42(10) . . ? O12 Tb1 N3 88.92(10) . . ? O11 Tb1 N3 119.79(9) . . ? O1 Tb1 N3 72.32(9) . . ? N4 Tb1 N3 168.75(10) . . ? C8 N1 C9 114.7(3) . . ? C8 N1 Zn1 123.7(2) . . ? C9 N1 Zn1 120.8(2) . . ? C14 N2 C13 116.7(3) . . ? C14 N2 Zn1 126.3(2) . . ? C13 N2 Zn1 116.9(2) . . ? O7 N3 O5 122.0(3) . . ? O7 N3 O6 122.0(4) . . ? O5 N3 O6 116.0(3) . . ? O7 N3 Tb1 178.2(3) . . ? O5 N3 Tb1 57.60(15) . . ? O6 N3 Tb1 58.47(16) . . ? O10 N4 O9 122.6(4) . . ? O10 N4 O8 120.7(4) . . ? O9 N4 O8 116.6(3) . . ? O10 N4 Tb1 173.4(3) . . ? O9 N4 Tb1 59.50(17) . . ? O8 N4 Tb1 57.50(17) . . ? O13 N5 O12 123.6(4) . . ? O13 N5 O11 120.0(4) . . ? O12 N5 O11 116.4(3) . . ? O13 N5 Tb1 176.5(5) . . ? O12 N5 Tb1 57.66(18) . . ? O11 N5 Tb1 58.85(17) . . ? C2 O1 C1 116.5(3) . . ? C2 O1 Tb1 116.09(17) . . ? C1 O1 Tb1 124.2(2) . . ? C7 O2 Zn1 126.93(18) . . ? C7 O2 Tb1 124.43(18) . . ? Zn1 O2 Tb1 108.07(9) . . ? C20 O3 Zn1 127.70(18) . . ? C20 O3 Tb1 123.32(18) . . ? Zn1 O3 Tb1 108.97(9) . . ? C19 O4 C21 116.5(3) . . ? C19 O4 Tb1 116.27(17) . . ? C21 O4 Tb1 127.2(2) . . ? N3 O5 Tb1 97.43(19) . . ? N3 O6 Tb1 96.2(2) . . ? N4 O8 Tb1 96.9(2) . . ? N4 O9 Tb1 95.1(2) . . ? N5 O11 Tb1 95.9(2) . . ? N5 O12 Tb1 97.5(2) . . ? Zn1 O14 H1W 117(3) . . ? Zn1 O14 H2W 114(3) . . ? H1W O14 H2W 101(4) . . ? O3 Zn1 N2 88.74(10) . . ? O3 Zn1 O2 76.42(8) . . ? N2 Zn1 O2 159.75(10) . . ? O3 Zn1 O14 110.34(10) . . ? N2 Zn1 O14 99.74(11) . . ? O2 Zn1 O14 98.33(11) . . ? O3 Zn1 N1 150.33(10) . . ? N2 Zn1 N1 97.40(10) . . ? O2 Zn1 N1 89.31(10) . . ? O14 Zn1 N1 97.24(11) . . ? O3 Zn1 Tb1 37.93(6) . . ? N2 Zn1 Tb1 124.57(8) . . ? O2 Zn1 Tb1 38.62(6) . . ? O14 Zn1 Tb1 110.75(8) . . ? N1 Zn1 Tb1 122.01(8) . . ? _diffrn_measured_fraction_theta_max 0.979 _diffrn_reflns_theta_full 33.36 _diffrn_measured_fraction_theta_full 0.979 _refine_diff_density_max 1.163 _refine_diff_density_min -1.847 _refine_diff_density_rms 0.117 data_tr34 _database_code_depnum_ccdc_archive 'CCDC 866883' #TrackingRef 'C3_tr34.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C21 H28 Gd N5 O15 Zn' _chemical_formula_weight 813.09 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Gd Gd -0.1653 3.9035 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Zn Zn 0.2839 1.4301 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Triclinic _symmetry_space_group_name_H-M P-1 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 8.9096(6) _cell_length_b 13.3969(9) _cell_length_c 13.3013(9) _cell_angle_alpha 83.137(5) _cell_angle_beta 73.461(5) _cell_angle_gamma 71.472(5) _cell_volume 1442.35(17) _cell_formula_units_Z 2 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 65431 _cell_measurement_theta_min 2.25 _cell_measurement_theta_max 33.80 _exptl_crystal_description prism _exptl_crystal_colour yellow _exptl_crystal_size_max 0.5 _exptl_crystal_size_mid 0.25 _exptl_crystal_size_min 0.12 _exptl_crystal_density_meas 'not measured' _exptl_crystal_density_diffrn 1.868 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 802 _exptl_absorpt_coefficient_mu 3.190 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.3036 _exptl_absorpt_correction_T_max 0.7161 _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 293(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'STOE-IPDS II' _diffrn_measurement_method 'omega scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 27400 _diffrn_reflns_av_R_equivalents 0.0482 _diffrn_reflns_av_sigmaI/netI 0.0431 _diffrn_reflns_limit_h_min -13 _diffrn_reflns_limit_h_max 12 _diffrn_reflns_limit_k_min -20 _diffrn_reflns_limit_k_max 20 _diffrn_reflns_limit_l_min -20 _diffrn_reflns_limit_l_max 20 _diffrn_reflns_theta_min 2.59 _diffrn_reflns_theta_max 33.44 _reflns_number_total 10676 _reflns_number_gt 9192 _reflns_threshold_expression >2sigma(I) _computing_data_collection X-Area _computing_cell_refinement X-Area _computing_data_reduction X-Area _computing_structure_solution 'SHELXS-97 (Sheldrick, 1997)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics ? _computing_publication_material ? _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^)+(0.0516P)^2^+0.4443P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment mixed _refine_ls_extinction_method SHELXL _refine_ls_extinction_coef 0.0285(9) _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_number_reflns 10676 _refine_ls_number_parameters 397 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0477 _refine_ls_R_factor_gt 0.0377 _refine_ls_wR_factor_ref 0.0923 _refine_ls_wR_factor_gt 0.0883 _refine_ls_goodness_of_fit_ref 1.038 _refine_ls_restrained_S_all 1.038 _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 C1 C 0.5912(5) 0.1137(3) 0.5012(3) 0.0521(9) Uani 1 1 d . . . H1A H 0.5834 0.0540 0.5478 0.078 Uiso 1 1 calc R . . H1B H 0.6670 0.0901 0.4351 0.078 Uiso 1 1 calc R . . H1C H 0.4852 0.1512 0.4906 0.078 Uiso 1 1 calc R . . C2 C 0.6678(4) 0.2721(3) 0.4888(2) 0.0334(5) Uani 1 1 d . . . C3 C 0.6480(4) 0.2979(3) 0.3889(2) 0.0421(7) Uani 1 1 d . . . H3 H 0.6241 0.2514 0.3535 0.051 Uiso 1 1 calc R . . C4 C 0.6638(5) 0.3937(3) 0.3409(2) 0.0466(8) Uani 1 1 d . . . H4 H 0.6523 0.4105 0.2730 0.056 Uiso 1 1 calc R . . C5 C 0.6963(4) 0.4630(3) 0.3933(2) 0.0390(6) Uani 1 1 d . . . H5 H 0.7018 0.5280 0.3619 0.047 Uiso 1 1 calc R . . C6 C 0.7215(4) 0.4369(2) 0.49440(19) 0.0313(5) Uani 1 1 d . . . C7 C 0.7103(3) 0.3395(2) 0.54209(19) 0.0290(5) Uani 1 1 d . . . C8 C 0.7473(4) 0.5177(2) 0.5447(2) 0.0340(5) Uani 1 1 d . . . H8 H 0.7374 0.5824 0.5086 0.041 Uiso 1 1 calc R . . C9 C 0.8069(5) 0.6076(3) 0.6605(3) 0.0435(7) Uani 1 1 d . . . H9A H 0.7345 0.6683 0.6330 0.052 Uiso 1 1 calc R . . H9B H 0.9187 0.6072 0.6257 0.052 Uiso 1 1 calc R . . C10 C 0.7763(5) 0.6210(2) 0.7779(3) 0.0401(6) Uani 1 1 d . . . C11 C 0.8048(8) 0.7263(3) 0.7880(4) 0.0685(14) Uani 1 1 d . . . H11A H 0.7268 0.7828 0.7614 0.103 Uiso 1 1 calc R . . H11B H 0.9139 0.7248 0.7484 0.103 Uiso 1 1 calc R . . H11C H 0.7915 0.7371 0.8604 0.103 Uiso 1 1 calc R . . C12 C 0.6015(5) 0.6234(4) 0.8385(3) 0.0544(9) Uani 1 1 d . . . H12A H 0.5248 0.6773 0.8085 0.082 Uiso 1 1 calc R . . H12B H 0.5837 0.6380 0.9106 0.082 Uiso 1 1 calc R . . H12C H 0.5863 0.5563 0.8346 0.082 Uiso 1 1 calc R . . C13 C 0.9027(4) 0.5364(3) 0.8233(3) 0.0389(6) Uani 1 1 d . . . H13A H 1.0105 0.5276 0.7753 0.047 Uiso 1 1 calc R . . H13B H 0.9040 0.5599 0.8891 0.047 Uiso 1 1 calc R . . C14 C 0.8700(4) 0.3899(2) 0.9326(2) 0.0352(6) Uani 1 1 d . . . H14 H 0.8905 0.4265 0.9799 0.042 Uiso 1 1 calc R . . C15 C 0.8419(4) 0.2899(3) 0.9705(2) 0.0350(6) Uani 1 1 d . . . C16 C 0.8611(5) 0.2539(3) 1.0721(2) 0.0452(8) Uani 1 1 d . . . H16 H 0.8912 0.2945 1.1104 0.054 Uiso 1 1 calc R . . C17 C 0.8363(5) 0.1612(3) 1.1144(3) 0.0508(9) Uani 1 1 d . . . H17 H 0.8504 0.1388 1.1809 0.061 Uiso 1 1 calc R . . C18 C 0.7897(5) 0.0991(3) 1.0582(3) 0.0456(7) Uani 1 1 d . . . H18 H 0.7733 0.0354 1.0869 0.055 Uiso 1 1 calc R . . C19 C 0.7685(4) 0.1339(2) 0.9599(2) 0.0355(6) Uani 1 1 d . . . C20 C 0.7942(4) 0.2295(2) 0.9135(2) 0.0307(5) Uani 1 1 d . . . C21 C 0.7176(6) -0.0249(3) 0.9319(3) 0.0526(9) Uani 1 1 d . . . H21A H 0.6837 -0.0545 0.8830 0.079 Uiso 1 1 calc R . . H21B H 0.6420 -0.0234 0.9999 0.079 Uiso 1 1 calc R . . H21C H 0.8254 -0.0673 0.9359 0.079 Uiso 1 1 calc R . . Gd1 Gd 0.630048(17) 0.181784(10) 0.743556(9) 0.02749(5) Uani 1 1 d . . . N1 N 0.7822(3) 0.51144(19) 0.63307(18) 0.0321(5) Uani 1 1 d . . . N2 N 0.8700(3) 0.4341(2) 0.84166(19) 0.0330(5) Uani 1 1 d . . . N3 N 0.9081(4) -0.0004(3) 0.6533(3) 0.0483(7) Uani 1 1 d . . . N4 N 0.3570(4) 0.3395(3) 0.8721(3) 0.0554(9) Uani 1 1 d . . . N5 N 0.3283(4) 0.1235(3) 0.7596(3) 0.0576(9) Uani 1 1 d . . . O1 O 0.6484(3) 0.18235(19) 0.54638(16) 0.0387(5) Uani 1 1 d . . . O2 O 0.7348(3) 0.30772(17) 0.63587(15) 0.0342(4) Uani 1 1 d . . . O3 O 0.7679(3) 0.25841(16) 0.81973(15) 0.0346(4) Uani 1 1 d . . . O4 O 0.7204(3) 0.08021(18) 0.89743(18) 0.0403(5) Uani 1 1 d . . . O5 O 0.7629(4) -0.0039(2) 0.6830(2) 0.0503(6) Uani 1 1 d . . . O6 O 0.9293(3) 0.0850(2) 0.6662(2) 0.0515(6) Uani 1 1 d . . . O7 O 1.0206(5) -0.0749(3) 0.6132(4) 0.0907(13) Uani 1 1 d . . . O8 O 0.4117(4) 0.2464(3) 0.90602(19) 0.0539(7) Uani 1 1 d . . . O9 O 0.4373(4) 0.3642(2) 0.7835(2) 0.0572(7) Uani 1 1 d . . . O10 O 0.2328(5) 0.4002(4) 0.9228(3) 0.0941(14) Uani 1 1 d . . . O11 O 0.3503(3) 0.2082(2) 0.7130(2) 0.0472(6) Uani 1 1 d . . . O12 O 0.4454(4) 0.0629(3) 0.7928(3) 0.0595(8) Uani 1 1 d . . . O13 O 0.2039(6) 0.1023(5) 0.7685(5) 0.126(2) Uani 1 1 d . . . O14 O 1.0787(3) 0.3147(2) 0.6355(2) 0.0406(5) Uani 1 1 d . . . O15 O 1.1603(5) 0.1590(3) 0.5034(3) 0.0779(11) Uani 1 1 d . . . Zn1 Zn 0.83870(4) 0.37230(3) 0.71908(2) 0.02990(7) Uani 1 1 d . . . H1W H 1.143(7) 0.290(4) 0.664(4) 0.065(16) Uiso 1 1 d . . . H2W H 1.094(8) 0.267(5) 0.580(5) 0.087(19) Uiso 1 1 d . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 C1 0.061(2) 0.057(2) 0.0529(18) -0.0149(16) -0.0170(17) -0.0307(19) C2 0.0301(13) 0.0420(15) 0.0287(11) -0.0078(10) -0.0073(9) -0.0095(11) C3 0.0441(17) 0.0549(19) 0.0305(12) -0.0093(12) -0.0137(12) -0.0128(15) C4 0.052(2) 0.059(2) 0.0277(12) -0.0016(12) -0.0155(12) -0.0110(17) C5 0.0389(16) 0.0456(17) 0.0292(11) 0.0043(11) -0.0108(11) -0.0085(13) C6 0.0319(13) 0.0362(13) 0.0245(10) -0.0005(9) -0.0059(9) -0.0100(11) C7 0.0284(12) 0.0341(12) 0.0247(9) -0.0033(9) -0.0069(9) -0.0089(10) C8 0.0352(14) 0.0307(13) 0.0334(11) 0.0029(10) -0.0079(10) -0.0086(11) C9 0.060(2) 0.0308(14) 0.0464(15) 0.0029(12) -0.0192(15) -0.0203(15) C10 0.0485(18) 0.0283(13) 0.0495(16) -0.0062(11) -0.0188(14) -0.0126(13) C11 0.106(4) 0.0308(16) 0.087(3) -0.0064(18) -0.050(3) -0.021(2) C12 0.0440(19) 0.057(2) 0.059(2) -0.0194(17) -0.0139(16) -0.0029(17) C13 0.0412(16) 0.0360(14) 0.0469(15) -0.0072(12) -0.0154(13) -0.0159(13) C14 0.0369(14) 0.0377(14) 0.0345(12) -0.0108(10) -0.0135(11) -0.0087(12) C15 0.0364(14) 0.0411(15) 0.0294(11) -0.0039(10) -0.0128(10) -0.0093(12) C16 0.0495(19) 0.057(2) 0.0331(13) -0.0025(13) -0.0201(13) -0.0134(16) C17 0.057(2) 0.064(2) 0.0324(13) 0.0105(14) -0.0207(14) -0.0161(19) C18 0.052(2) 0.0455(18) 0.0389(14) 0.0127(13) -0.0173(14) -0.0144(16) C19 0.0369(15) 0.0344(14) 0.0349(12) 0.0032(10) -0.0117(11) -0.0100(12) C20 0.0341(13) 0.0318(12) 0.0270(10) -0.0002(9) -0.0109(9) -0.0087(11) C21 0.064(2) 0.0314(15) 0.067(2) 0.0126(15) -0.028(2) -0.0164(16) Gd1 0.03085(7) 0.02461(6) 0.02803(6) -0.00166(4) -0.00752(4) -0.00954(5) N1 0.0361(12) 0.0276(10) 0.0336(10) -0.0011(8) -0.0103(9) -0.0099(9) N2 0.0370(13) 0.0299(11) 0.0358(10) -0.0056(8) -0.0127(9) -0.0105(10) N3 0.0472(17) 0.0409(15) 0.0515(15) -0.0135(12) -0.0083(13) -0.0059(13) N4 0.0483(18) 0.063(2) 0.0475(15) -0.0238(15) -0.0137(13) 0.0028(16) N5 0.0450(18) 0.072(2) 0.0639(19) 0.0229(17) -0.0216(15) -0.0314(18) O1 0.0470(13) 0.0433(12) 0.0348(9) -0.0059(8) -0.0123(9) -0.0225(10) O2 0.0494(13) 0.0356(10) 0.0271(8) 0.0020(7) -0.0156(8) -0.0219(10) O3 0.0531(13) 0.0298(9) 0.0279(8) 0.0038(7) -0.0172(8) -0.0177(9) O4 0.0555(15) 0.0292(10) 0.0423(10) 0.0068(8) -0.0208(10) -0.0169(10) O5 0.0485(15) 0.0355(12) 0.0662(16) -0.0122(11) -0.0063(12) -0.0152(11) O6 0.0394(13) 0.0478(14) 0.0668(16) -0.0162(12) -0.0070(12) -0.0131(12) O7 0.058(2) 0.063(2) 0.130(3) -0.047(2) -0.002(2) 0.0078(18) O8 0.0503(15) 0.0656(18) 0.0366(11) -0.0045(11) -0.0050(10) -0.0092(14) O9 0.0642(19) 0.0377(13) 0.0602(16) -0.0039(11) -0.0155(14) -0.0022(13) O10 0.068(2) 0.100(3) 0.084(2) -0.049(2) -0.0092(19) 0.025(2) O11 0.0433(13) 0.0551(15) 0.0473(12) 0.0131(11) -0.0185(10) -0.0197(12) O12 0.0448(15) 0.0543(17) 0.084(2) 0.0246(15) -0.0280(14) -0.0211(14) O13 0.075(3) 0.148(5) 0.191(5) 0.101(4) -0.083(3) -0.080(3) O14 0.0356(12) 0.0417(12) 0.0433(11) -0.0034(9) -0.0117(10) -0.0082(10) O15 0.093(3) 0.073(2) 0.071(2) -0.0254(17) 0.0054(19) -0.044(2) Zn1 0.03798(17) 0.02680(14) 0.02881(13) -0.00119(10) -0.01209(12) -0.01190(13) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag C1 O1 1.439(4) . ? C1 H1A 0.9600 . ? C1 H1B 0.9600 . ? C1 H1C 0.9600 . ? C2 O1 1.378(4) . ? C2 C3 1.380(4) . ? C2 C7 1.408(4) . ? C3 C4 1.394(6) . ? C3 H3 0.9300 . ? C4 C5 1.368(5) . ? C4 H4 0.9300 . ? C5 C6 1.411(4) . ? C5 H5 0.9300 . ? C6 C7 1.401(4) . ? C6 C8 1.446(4) . ? C7 O2 1.324(3) . ? C8 N1 1.286(4) . ? C8 H8 0.9300 . ? C9 N1 1.476(4) . ? C9 C10 1.530(5) . ? C9 H9A 0.9700 . ? C9 H9B 0.9700 . ? C10 C13 1.527(5) . ? C10 C12 1.528(6) . ? C10 C11 1.538(5) . ? C11 H11A 0.9600 . ? C11 H11B 0.9600 . ? C11 H11C 0.9600 . ? C12 H12A 0.9600 . ? C12 H12B 0.9600 . ? C12 H12C 0.9600 . ? C13 N2 1.468(4) . ? C13 H13A 0.9700 . ? C13 H13B 0.9700 . ? C14 N2 1.282(4) . ? C14 C15 1.446(5) . ? C14 H14 0.9300 . ? C15 C20 1.400(4) . ? C15 C16 1.418(4) . ? C16 C17 1.358(6) . ? C16 H16 0.9300 . ? C17 C18 1.403(6) . ? C17 H17 0.9300 . ? C18 C19 1.380(4) . ? C18 H18 0.9300 . ? C19 O4 1.390(4) . ? C19 C20 1.411(4) . ? C20 O3 1.325(3) . ? C21 O4 1.434(4) . ? C21 H21A 0.9600 . ? C21 H21B 0.9600 . ? C21 H21C 0.9600 . ? Gd1 O3 2.312(2) . ? Gd1 O2 2.330(2) . ? Gd1 O8 2.487(3) . ? Gd1 O4 2.503(2) . ? Gd1 O5 2.510(3) . ? Gd1 O9 2.516(3) . ? Gd1 O6 2.532(3) . ? Gd1 O12 2.545(3) . ? Gd1 O11 2.546(3) . ? Gd1 O1 2.580(2) . ? Gd1 N4 2.921(3) . ? Gd1 N3 2.950(3) . ? N1 Zn1 2.064(2) . ? N2 Zn1 2.037(2) . ? N3 O7 1.214(4) . ? N3 O5 1.255(4) . ? N3 O6 1.256(4) . ? N4 O10 1.215(4) . ? N4 O9 1.260(5) . ? N4 O8 1.265(5) . ? N5 O13 1.201(5) . ? N5 O12 1.257(4) . ? N5 O11 1.271(4) . ? O2 Zn1 2.0379(19) . ? O3 Zn1 2.040(2) . ? O14 Zn1 2.051(3) . ? O14 H1W 0.75(6) . ? O14 H2W 0.99(6) . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag O1 C1 H1A 109.5 . . ? O1 C1 H1B 109.5 . . ? H1A C1 H1B 109.5 . . ? O1 C1 H1C 109.5 . . ? H1A C1 H1C 109.5 . . ? H1B C1 H1C 109.5 . . ? O1 C2 C3 125.5(3) . . ? O1 C2 C7 113.5(2) . . ? C3 C2 C7 121.0(3) . . ? C2 C3 C4 119.9(3) . . ? C2 C3 H3 120.0 . . ? C4 C3 H3 120.0 . . ? C5 C4 C3 120.2(3) . . ? C5 C4 H4 119.9 . . ? C3 C4 H4 119.9 . . ? C4 C5 C6 120.8(3) . . ? C4 C5 H5 119.6 . . ? C6 C5 H5 119.6 . . ? C7 C6 C5 119.4(3) . . ? C7 C6 C8 124.2(2) . . ? C5 C6 C8 116.2(3) . . ? O2 C7 C6 123.6(2) . . ? O2 C7 C2 117.8(3) . . ? C6 C7 C2 118.6(2) . . ? N1 C8 C6 128.2(3) . . ? N1 C8 H8 115.9 . . ? C6 C8 H8 115.9 . . ? N1 C9 C10 115.2(3) . . ? N1 C9 H9A 108.5 . . ? C10 C9 H9A 108.5 . . ? N1 C9 H9B 108.5 . . ? C10 C9 H9B 108.5 . . ? H9A C9 H9B 107.5 . . ? C13 C10 C12 111.2(3) . . ? C13 C10 C9 111.3(3) . . ? C12 C10 C9 111.8(3) . . ? C13 C10 C11 106.1(3) . . ? C12 C10 C11 110.0(4) . . ? C9 C10 C11 106.2(3) . . ? C10 C11 H11A 109.5 . . ? C10 C11 H11B 109.5 . . ? H11A C11 H11B 109.5 . . ? C10 C11 H11C 109.5 . . ? H11A C11 H11C 109.5 . . ? H11B C11 H11C 109.5 . . ? C10 C12 H12A 109.5 . . ? C10 C12 H12B 109.5 . . ? H12A C12 H12B 109.5 . . ? C10 C12 H12C 109.5 . . ? H12A C12 H12C 109.5 . . ? H12B C12 H12C 109.5 . . ? N2 C13 C10 113.3(3) . . ? N2 C13 H13A 108.9 . . ? C10 C13 H13A 108.9 . . ? N2 C13 H13B 108.9 . . ? C10 C13 H13B 108.9 . . ? H13A C13 H13B 107.7 . . ? N2 C14 C15 127.7(2) . . ? N2 C14 H14 116.1 . . ? C15 C14 H14 116.1 . . ? C20 C15 C16 119.4(3) . . ? C20 C15 C14 123.6(2) . . ? C16 C15 C14 117.1(3) . . ? C17 C16 C15 121.2(3) . . ? C17 C16 H16 119.4 . . ? C15 C16 H16 119.4 . . ? C16 C17 C18 120.4(3) . . ? C16 C17 H17 119.8 . . ? C18 C17 H17 119.8 . . ? C19 C18 C17 119.0(3) . . ? C19 C18 H18 120.5 . . ? C17 C18 H18 120.5 . . ? C18 C19 O4 124.3(3) . . ? C18 C19 C20 122.0(3) . . ? O4 C19 C20 113.7(2) . . ? O3 C20 C15 123.7(3) . . ? O3 C20 C19 118.2(2) . . ? C15 C20 C19 118.1(2) . . ? O4 C21 H21A 109.5 . . ? O4 C21 H21B 109.5 . . ? H21A C21 H21B 109.5 . . ? O4 C21 H21C 109.5 . . ? H21A C21 H21C 109.5 . . ? H21B C21 H21C 109.5 . . ? O3 Gd1 O2 66.07(7) . . ? O3 Gd1 O8 80.44(9) . . ? O2 Gd1 O8 116.46(9) . . ? O3 Gd1 O4 65.16(7) . . ? O2 Gd1 O4 127.95(7) . . ? O8 Gd1 O4 71.62(9) . . ? O3 Gd1 O5 119.29(9) . . ? O2 Gd1 O5 115.03(9) . . ? O8 Gd1 O5 128.45(10) . . ? O4 Gd1 O5 75.53(9) . . ? O3 Gd1 O9 76.25(10) . . ? O2 Gd1 O9 69.07(10) . . ? O8 Gd1 O9 50.78(10) . . ? O4 Gd1 O9 114.60(9) . . ? O5 Gd1 O9 164.45(10) . . ? O3 Gd1 O6 76.26(9) . . ? O2 Gd1 O6 75.56(9) . . ? O8 Gd1 O6 146.14(10) . . ? O4 Gd1 O6 76.40(9) . . ? O5 Gd1 O6 49.96(9) . . ? O9 Gd1 O6 141.65(11) . . ? O3 Gd1 O12 140.03(9) . . ? O2 Gd1 O12 152.59(8) . . ? O8 Gd1 O12 71.09(11) . . ? O4 Gd1 O12 79.32(9) . . ? O5 Gd1 O12 64.55(10) . . ? O9 Gd1 O12 104.53(11) . . ? O6 Gd1 O12 113.73(10) . . ? O3 Gd1 O11 142.19(9) . . ? O2 Gd1 O11 105.76(8) . . ? O8 Gd1 O11 70.50(9) . . ? O4 Gd1 O11 123.79(8) . . ? O5 Gd1 O11 97.91(9) . . ? O9 Gd1 O11 66.77(10) . . ? O6 Gd1 O11 139.73(9) . . ? O12 Gd1 O11 49.84(9) . . ? O3 Gd1 O1 126.90(7) . . ? O2 Gd1 O1 63.11(7) . . ? O8 Gd1 O1 136.50(9) . . ? O4 Gd1 O1 146.62(8) . . ? O5 Gd1 O1 71.86(9) . . ? O9 Gd1 O1 98.79(9) . . ? O6 Gd1 O1 77.35(9) . . ? O12 Gd1 O1 92.84(9) . . ? O11 Gd1 O1 68.54(8) . . ? O3 Gd1 N4 78.85(9) . . ? O2 Gd1 N4 93.39(10) . . ? O8 Gd1 N4 25.48(10) . . ? O4 Gd1 N4 94.15(9) . . ? O5 Gd1 N4 150.32(11) . . ? O9 Gd1 N4 25.42(11) . . ? O6 Gd1 N4 155.09(10) . . ? O12 Gd1 N4 86.38(12) . . ? O11 Gd1 N4 64.45(10) . . ? O1 Gd1 N4 117.90(9) . . ? O3 Gd1 N3 98.20(9) . . ? O2 Gd1 N3 95.31(9) . . ? O8 Gd1 N3 143.55(10) . . ? O4 Gd1 N3 74.85(9) . . ? O5 Gd1 N3 24.94(9) . . ? O9 Gd1 N3 164.38(11) . . ? O6 Gd1 N3 25.03(9) . . ? O12 Gd1 N3 89.16(10) . . ? O11 Gd1 N3 119.56(10) . . ? O1 Gd1 N3 72.61(9) . . ? N4 Gd1 N3 168.74(10) . . ? C8 N1 C9 114.7(3) . . ? C8 N1 Zn1 123.3(2) . . ? C9 N1 Zn1 121.22(19) . . ? C14 N2 C13 116.7(2) . . ? C14 N2 Zn1 125.9(2) . . ? C13 N2 Zn1 117.32(19) . . ? O7 N3 O5 121.8(4) . . ? O7 N3 O6 122.2(4) . . ? O5 N3 O6 116.0(3) . . ? O7 N3 Gd1 177.8(3) . . ? O5 N3 Gd1 57.53(17) . . ? O6 N3 Gd1 58.52(18) . . ? O10 N4 O9 122.7(4) . . ? O10 N4 O8 120.9(4) . . ? O9 N4 O8 116.4(3) . . ? O10 N4 Gd1 173.2(3) . . ? O9 N4 Gd1 59.01(18) . . ? O8 N4 Gd1 57.74(17) . . ? O13 N5 O12 122.5(4) . . ? O13 N5 O11 121.3(4) . . ? O12 N5 O11 116.2(3) . . ? O13 N5 Gd1 177.9(5) . . ? O12 N5 Gd1 58.10(19) . . ? O11 N5 Gd1 58.22(17) . . ? C2 O1 C1 117.0(3) . . ? C2 O1 Gd1 116.13(15) . . ? C1 O1 Gd1 124.0(2) . . ? C7 O2 Zn1 126.84(18) . . ? C7 O2 Gd1 124.44(17) . . ? Zn1 O2 Gd1 108.19(8) . . ? C20 O3 Zn1 127.70(18) . . ? C20 O3 Gd1 123.50(18) . . ? Zn1 O3 Gd1 108.81(8) . . ? C19 O4 C21 116.6(3) . . ? C19 O4 Gd1 116.37(17) . . ? C21 O4 Gd1 126.9(2) . . ? N3 O5 Gd1 97.5(2) . . ? N3 O6 Gd1 96.5(2) . . ? N4 O8 Gd1 96.8(2) . . ? N4 O9 Gd1 95.6(2) . . ? N5 O11 Gd1 96.7(2) . . ? N5 O12 Gd1 97.1(2) . . ? Zn1 O14 H1W 119(4) . . ? Zn1 O14 H2W 113(4) . . ? H1W O14 H2W 108(5) . . ? N2 Zn1 O2 159.77(10) . . ? N2 Zn1 O3 88.74(9) . . ? O2 Zn1 O3 76.72(8) . . ? N2 Zn1 O14 99.88(11) . . ? O2 Zn1 O14 98.34(10) . . ? O3 Zn1 O14 110.25(10) . . ? N2 Zn1 N1 96.90(10) . . ? O2 Zn1 N1 89.44(9) . . ? O3 Zn1 N1 150.59(10) . . ? O14 Zn1 N1 97.22(10) . . ? N2 Zn1 Gd1 124.79(8) . . ? O2 Zn1 Gd1 38.68(6) . . ? O3 Zn1 Gd1 38.16(5) . . ? O14 Zn1 Gd1 110.55(8) . . ? N1 Zn1 Gd1 122.31(7) . . ? _diffrn_measured_fraction_theta_max 0.947 _diffrn_reflns_theta_full 33.44 _diffrn_measured_fraction_theta_full 0.947 _refine_diff_density_max 1.340 _refine_diff_density_min -1.977 _refine_diff_density_rms 0.119