# Supplementary Material (ESI) for Chemical Communications # This journal is (c) The Royal Society of Chemistry 2009 data_global _journal_name_full Chem.Commun. _journal_coden_cambridge 0182 _journal_year ? _journal_volume ? _journal_page_first ? _publ_contact_author_name 'Cyrille Train' _publ_contact_author_email CYRILLE.TRAIN@UPMC.FR loop_ _publ_author_name C.Train L.-M.Chamoreau G.Chastanet Y.Journaux L.Norel data_ln617 _database_code_depnum_ccdc_archive 'CCDC 699835' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C22 H12 F18 Gd N6 O7' _chemical_formula_sum 'C22 H12 F18 Gd N6 O7' _chemical_formula_weight 971.63 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' F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M 'P 21/c' _symmetry_space_group_name_Hall '-P 2ybc' _symmetry_Int_Tables_number 14 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 11.3388(18) _cell_length_b 18.522(3) _cell_length_c 16.6033(12) _cell_angle_alpha 90.00 _cell_angle_beta 107.621(7) _cell_angle_gamma 90.00 _cell_volume 3323.3(8) _cell_formula_units_Z 4 _cell_measurement_temperature 200(2) _cell_measurement_reflns_used 127 _cell_measurement_theta_min 3.7 _cell_measurement_theta_max 22.4 _exptl_crystal_description needle _exptl_crystal_colour orange _exptl_crystal_size_max 0.26 _exptl_crystal_size_mid 0.11 _exptl_crystal_size_min 0.04 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.942 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1872 _exptl_absorpt_coefficient_mu 2.146 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.765 _exptl_absorpt_correction_T_max 0.918 _exptl_absorpt_process_details ; R.H. Blessing, Acta Cryst. (1995), A51, 33-38 ; _diffrn_ambient_temperature 200(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 KappaCCD _diffrn_measurement_method 'CCD rotation images, thick slices' _diffrn_detector_area_resol_mean 9 _diffrn_standards_number 0 _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% 0 _diffrn_reflns_number 44399 _diffrn_reflns_av_R_equivalents 0.0651 _diffrn_reflns_av_sigmaI/netI 0.0821 _diffrn_reflns_limit_h_min -15 _diffrn_reflns_limit_h_max 15 _diffrn_reflns_limit_k_min -26 _diffrn_reflns_limit_k_max 26 _diffrn_reflns_limit_l_min -16 _diffrn_reflns_limit_l_max 22 _diffrn_reflns_theta_min 1.69 _diffrn_reflns_theta_max 30.01 _reflns_number_total 9124 _reflns_number_gt 5590 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Collect (Nonius BV, 1997-2000)' _computing_cell_refinement 'Dirax/lsq (Duisenberg & Schreurs, 1989-2000)' _computing_data_reduction 'EvalCCD (Duisenberg & Schreurs 1990-2000)' _computing_structure_solution 'SIR92 (Giacovazzo et al, 1993)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'DIAMOND (Brandenburg, 1999)' _computing_publication_material 'WinGX publication routines (Farrugia, 1999)' _refine_special_details ; For _diffrn_reflns_theta_full 27.50 _diffrn_measured_fraction_theta_full 0.976 Essentially high theta values are mising because of a poor diffracting power of the needle. 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^)+(0.0492P)^2^+0.0963P] 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 9124 _refine_ls_number_parameters 487 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0963 _refine_ls_R_factor_gt 0.0391 _refine_ls_wR_factor_ref 0.1015 _refine_ls_wR_factor_gt 0.0833 _refine_ls_goodness_of_fit_ref 1.024 _refine_ls_restrained_S_all 1.024 _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 Gd 0.151612(18) 0.270559(11) 0.382876(11) 0.02405(7) Uani 1 1 d . . . O1 O 0.0351(3) 0.28876(16) 0.48163(17) 0.0332(7) Uani 1 1 d . . . O2 O 0.0024(3) 0.18379(17) 0.31043(17) 0.0364(7) Uani 1 1 d . . . O3 O 0.1597(3) 0.16320(16) 0.47436(18) 0.0396(8) Uani 1 1 d . . . O4 O 0.2837(3) 0.17908(16) 0.35323(17) 0.0342(7) Uani 1 1 d . . . O5 O 0.3431(3) 0.27367(16) 0.49592(18) 0.0372(7) Uani 1 1 d . . . O6 O 0.2841(3) 0.32855(17) 0.31671(17) 0.0378(7) Uani 1 1 d . . . O7 O 0.1911(3) 0.39073(16) 0.43920(17) 0.0338(7) Uani 1 1 d . . . N1 N 0.0483(3) 0.22096(19) 0.6848(2) 0.0303(8) Uani 1 1 d . . . N2 N 0.0787(3) 0.2565(2) 0.6211(2) 0.0311(8) Uani 1 1 d . . . N3 N -0.1013(3) 0.2161(2) 0.5211(2) 0.0333(9) Uani 1 1 d . . . N4 N -0.1368(3) 0.1787(2) 0.5813(2) 0.0330(8) Uani 1 1 d . . . N5 N -0.1862(3) 0.0965(2) 0.7103(2) 0.0353(9) Uani 1 1 d . . . H5 H -0.2365 0.0858 0.6616 0.042 Uiso 1 1 calc R . . N6 N -0.0313(3) 0.14894(19) 0.80770(19) 0.0287(8) Uani 1 1 d . . . C1 C 0.0054(4) 0.2555(2) 0.5381(3) 0.0291(10) Uani 1 1 d . . . C2 C -0.0574(4) 0.1844(2) 0.6592(2) 0.0256(9) Uani 1 1 d . . . C3 C -0.0917(4) 0.1443(2) 0.7253(2) 0.0267(9) Uani 1 1 d . . . C4 C -0.1880(4) 0.0681(2) 0.7863(3) 0.0380(11) Uani 1 1 d . . . H4 H -0.2426 0.0338 0.7954 0.046 Uiso 1 1 calc R . . C5 C -0.0932(4) 0.1006(2) 0.8455(3) 0.0343(10) Uani 1 1 d . . . H5A H -0.0723 0.0920 0.9033 0.041 Uiso 1 1 calc R . . C6 C 0.1949(5) 0.2973(3) 0.6459(3) 0.0514(14) Uani 1 1 d . . . H6A H 0.2511 0.2769 0.6189 0.077 Uiso 1 1 calc R . . H6B H 0.2311 0.2949 0.7061 0.077 Uiso 1 1 calc R . . H6C H 0.1787 0.3468 0.6289 0.077 Uiso 1 1 calc R . . C7 C -0.1897(4) 0.2140(3) 0.4349(3) 0.0507(15) Uani 1 1 d . . . H7A H -0.2520 0.2503 0.4298 0.076 Uiso 1 1 calc R . . H7B H -0.2280 0.1673 0.4247 0.076 Uiso 1 1 calc R . . H7C H -0.1465 0.2231 0.3944 0.076 Uiso 1 1 calc R . . C8 C -0.0053(4) 0.1159(3) 0.3145(3) 0.0437(12) Uani 1 1 d . . . C9 C 0.0555(4) 0.0705(3) 0.3804(3) 0.0498(13) Uani 1 1 d . . . H9 H 0.0459 0.0208 0.3736 0.060 Uiso 1 1 calc R . . C10 C 0.1310(4) 0.0985(3) 0.4569(3) 0.0415(11) Uani 1 1 d . . . C11 C -0.0984(6) 0.0823(4) 0.2370(4) 0.077(2) Uani 1 1 d . . . C12 C 0.1888(7) 0.0460(3) 0.5309(4) 0.0697(18) Uani 1 1 d . . . C13 C 0.3918(4) 0.1573(2) 0.3909(3) 0.0355(10) Uani 1 1 d . . . C14 C 0.4739(4) 0.1833(3) 0.4651(3) 0.0401(11) Uani 1 1 d . . . H14 H 0.5520 0.1625 0.4849 0.048 Uiso 1 1 calc R . . C15 C 0.4437(4) 0.2396(3) 0.5111(3) 0.0360(10) Uani 1 1 d . . . C16 C 0.4344(5) 0.0920(3) 0.3480(3) 0.0511(13) Uani 1 1 d . . . C17 C 0.5456(5) 0.2655(3) 0.5910(3) 0.0523(14) Uani 1 1 d . . . C18 C 0.3517(4) 0.3842(3) 0.3327(3) 0.0349(10) Uani 1 1 d . . . C19 C 0.3510(4) 0.4392(3) 0.3896(3) 0.0423(12) Uani 1 1 d . . . H19 H 0.4058 0.4776 0.3954 0.051 Uiso 1 1 calc R . . C20 C 0.2697(4) 0.4378(2) 0.4384(2) 0.0306(10) Uani 1 1 d . . . C21 C 0.4470(5) 0.3869(3) 0.2831(3) 0.0518(14) Uani 1 1 d . . . C22 C 0.2745(5) 0.4998(3) 0.5018(3) 0.0484(13) Uani 1 1 d . . . F1 F -0.0856(6) 0.1081(3) 0.1665(3) 0.171(3) Uani 1 1 d . . . F2 F -0.2125(4) 0.0970(3) 0.2352(3) 0.146(2) Uani 1 1 d . . . F3 F -0.0913(4) 0.0111(2) 0.2321(3) 0.1032(15) Uani 1 1 d . . . F4 F 0.1550(4) 0.0644(2) 0.5990(2) 0.0917(12) Uani 1 1 d . . . F5 F 0.3120(4) 0.0497(2) 0.5537(3) 0.0963(13) Uani 1 1 d . . . F6 F 0.1530(4) -0.02217(19) 0.5131(3) 0.1138(16) Uani 1 1 d . . . F7 F 0.3902(4) 0.0936(2) 0.2650(2) 0.0970(14) Uani 1 1 d . . . F8 F 0.3889(4) 0.03075(19) 0.3688(3) 0.0984(13) Uani 1 1 d . . . F9 F 0.5541(3) 0.0833(2) 0.3694(2) 0.0958(14) Uani 1 1 d . . . F10 F 0.6059(3) 0.2108(2) 0.6385(2) 0.0872(12) Uani 1 1 d . . . F11 F 0.5051(4) 0.3051(3) 0.6403(3) 0.147(2) Uani 1 1 d . . . F12 F 0.6355(4) 0.2983(3) 0.5697(2) 0.1046(14) Uani 1 1 d . . . F13 F 0.4822(4) 0.4536(2) 0.2721(2) 0.0972(14) Uani 1 1 d . . . F14 F 0.5482(3) 0.3512(3) 0.3251(2) 0.1021(14) Uani 1 1 d . . . F15 F 0.4039(3) 0.3574(2) 0.20753(19) 0.0822(11) Uani 1 1 d . . . F16 F 0.3419(3) 0.55632(17) 0.4920(2) 0.0797(11) Uani 1 1 d . . . F17 F 0.3243(4) 0.47607(19) 0.58064(19) 0.0909(13) Uani 1 1 d . . . F18 F 0.1627(3) 0.5248(2) 0.4951(2) 0.0806(11) 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 TB1 0.02437(11) 0.02510(11) 0.02458(12) 0.00044(9) 0.01024(7) 0.00066(10) O1 0.0351(17) 0.0413(19) 0.0283(16) 0.0071(13) 0.0170(13) 0.0001(13) O2 0.0334(17) 0.0343(18) 0.0389(17) -0.0001(14) 0.0070(13) -0.0025(14) O3 0.048(2) 0.0327(18) 0.0374(18) 0.0056(13) 0.0112(14) -0.0016(15) O4 0.0300(16) 0.0337(17) 0.0370(17) -0.0024(13) 0.0073(13) 0.0063(14) O5 0.0353(18) 0.0386(18) 0.0354(17) -0.0018(14) 0.0072(13) 0.0011(15) O6 0.0397(18) 0.043(2) 0.0367(17) -0.0028(14) 0.0198(14) -0.0049(15) O7 0.0369(17) 0.0329(17) 0.0354(17) -0.0056(13) 0.0163(13) -0.0036(14) N1 0.033(2) 0.037(2) 0.0220(18) 0.0039(14) 0.0103(14) -0.0059(16) N2 0.034(2) 0.043(2) 0.0190(19) 0.0021(15) 0.0122(15) -0.0111(17) N3 0.0278(19) 0.052(3) 0.0208(18) 0.0045(15) 0.0085(14) -0.0064(17) N4 0.032(2) 0.048(2) 0.0204(18) 0.0010(16) 0.0099(15) -0.0056(18) N5 0.036(2) 0.042(2) 0.029(2) 0.0014(16) 0.0092(16) -0.0137(18) N6 0.034(2) 0.032(2) 0.0238(19) 0.0006(14) 0.0145(15) -0.0058(16) C1 0.030(2) 0.034(2) 0.028(2) -0.0004(17) 0.0161(18) 0.0016(18) C2 0.027(2) 0.027(2) 0.024(2) 0.0010(17) 0.0107(16) -0.0008(18) C3 0.026(2) 0.032(2) 0.024(2) -0.0014(17) 0.0093(17) -0.0039(18) C4 0.040(3) 0.035(3) 0.042(3) 0.000(2) 0.017(2) -0.013(2) C5 0.042(3) 0.033(2) 0.031(2) 0.0076(18) 0.017(2) -0.007(2) C6 0.055(3) 0.067(4) 0.031(3) 0.002(2) 0.013(2) -0.028(3) C7 0.027(3) 0.094(5) 0.026(3) 0.009(2) 0.0022(19) -0.010(3) C8 0.035(3) 0.043(3) 0.050(3) -0.011(2) 0.009(2) -0.005(2) C9 0.051(3) 0.029(3) 0.068(4) 0.002(2) 0.015(3) -0.007(2) C10 0.047(3) 0.030(3) 0.050(3) 0.005(2) 0.019(2) -0.005(2) C11 0.064(5) 0.071(5) 0.085(5) -0.033(4) 0.003(4) -0.012(4) C12 0.080(5) 0.040(3) 0.079(5) 0.017(3) 0.008(4) -0.003(3) C13 0.035(3) 0.029(2) 0.044(3) 0.0040(19) 0.014(2) 0.007(2) C14 0.027(2) 0.044(3) 0.046(3) -0.003(2) 0.007(2) 0.006(2) C15 0.028(2) 0.042(3) 0.036(3) 0.002(2) 0.0061(19) -0.003(2) C16 0.041(3) 0.048(3) 0.059(4) -0.005(3) 0.008(2) 0.014(3) C17 0.038(3) 0.066(4) 0.047(3) -0.007(3) 0.004(2) -0.002(3) C18 0.033(2) 0.040(3) 0.033(2) 0.008(2) 0.0122(19) -0.003(2) C19 0.041(3) 0.039(3) 0.046(3) 0.002(2) 0.011(2) -0.009(2) C20 0.034(2) 0.024(2) 0.030(2) 0.0002(17) 0.0049(18) -0.0001(19) C21 0.045(3) 0.074(4) 0.045(3) -0.003(3) 0.027(2) -0.012(3) C22 0.061(4) 0.043(3) 0.043(3) -0.009(2) 0.018(2) -0.009(3) F1 0.273(7) 0.159(5) 0.048(3) -0.031(3) -0.001(3) -0.110(5) F2 0.068(3) 0.141(4) 0.181(5) -0.077(4) -0.036(3) 0.005(3) F3 0.096(3) 0.063(3) 0.126(3) -0.050(2) -0.003(2) -0.011(2) F4 0.125(3) 0.086(3) 0.065(2) 0.033(2) 0.030(2) -0.011(2) F5 0.083(3) 0.078(3) 0.115(3) 0.043(2) 0.013(2) 0.030(2) F6 0.167(4) 0.034(2) 0.120(3) 0.023(2) 0.011(3) -0.003(2) F7 0.126(3) 0.102(3) 0.055(2) -0.0203(19) 0.015(2) 0.068(3) F8 0.131(3) 0.043(2) 0.135(3) -0.019(2) 0.061(3) -0.009(2) F9 0.048(2) 0.090(3) 0.139(3) -0.054(2) 0.012(2) 0.027(2) F10 0.070(2) 0.122(3) 0.051(2) 0.016(2) -0.0099(17) 0.004(2) F11 0.066(3) 0.226(6) 0.110(3) -0.120(4) -0.034(2) 0.048(3) F12 0.086(3) 0.120(3) 0.089(3) -0.004(2) -0.001(2) -0.062(3) F13 0.123(3) 0.091(3) 0.111(3) -0.009(2) 0.086(3) -0.047(3) F14 0.051(2) 0.164(4) 0.105(3) 0.025(3) 0.044(2) 0.028(3) F15 0.088(3) 0.121(3) 0.055(2) -0.022(2) 0.0480(18) -0.030(2) F16 0.105(3) 0.042(2) 0.100(3) -0.0264(18) 0.043(2) -0.0318(19) F17 0.157(4) 0.067(2) 0.0337(18) -0.0147(16) 0.0064(19) -0.011(2) F18 0.077(3) 0.079(3) 0.095(3) -0.045(2) 0.039(2) 0.005(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 TB1 O6 2.370(3) . ? TB1 O2 2.379(3) . ? TB1 O5 2.403(3) . ? TB1 O7 2.403(3) . ? TB1 O4 2.409(3) . ? TB1 O1 2.420(3) . ? TB1 O3 2.487(3) . ? TB1 N6 2.552(3) 4_565 ? O1 C1 1.251(5) . ? O2 C8 1.263(5) . ? O3 C10 1.253(5) . ? O4 C13 1.262(5) . ? O5 C15 1.260(5) . ? O6 C18 1.264(5) . ? O7 C20 1.250(5) . ? N1 C2 1.329(5) . ? N1 N2 1.376(4) . ? N2 C1 1.376(5) . ? N2 C6 1.466(6) . ? N3 C1 1.367(5) . ? N3 N4 1.373(5) . ? N3 C7 1.478(5) . ? N4 C2 1.338(5) . ? N5 C3 1.354(5) . ? N5 C4 1.373(5) . ? N5 H5 0.8600 . ? N6 C3 1.335(5) . ? N6 C5 1.398(5) . ? N6 TB1 2.552(3) 4_566 ? C2 C3 1.471(5) . ? C4 C5 1.359(6) . ? C4 H4 0.9300 . ? C5 H5A 0.9300 . ? C6 H6A 0.9600 . ? C6 H6B 0.9600 . ? C6 H6C 0.9600 . ? C7 H7A 0.9600 . ? C7 H7B 0.9600 . ? C7 H7C 0.9600 . ? C8 C9 1.387(7) . ? C8 C11 1.528(7) . ? C9 C10 1.399(6) . ? C9 H9 0.9300 . ? C10 C12 1.548(7) . ? C11 F1 1.312(8) . ? C11 F2 1.314(8) . ? C11 F3 1.326(7) . ? C12 F6 1.331(7) . ? C12 F5 1.335(7) . ? C12 F4 1.343(7) . ? C13 C14 1.387(6) . ? C13 C16 1.552(7) . ? C14 C15 1.395(6) . ? C14 H14 0.9300 . ? C15 C17 1.548(7) . ? C16 F9 1.304(6) . ? C16 F7 1.316(6) . ? C16 F8 1.335(6) . ? C17 F11 1.283(6) . ? C17 F12 1.325(6) . ? C17 F10 1.337(7) . ? C18 C19 1.391(6) . ? C18 C21 1.545(6) . ? C19 C20 1.400(6) . ? C19 H19 0.9300 . ? C20 C22 1.547(6) . ? C21 F15 1.319(6) . ? C21 F14 1.326(6) . ? C21 F13 1.326(6) . ? C22 F18 1.323(6) . ? C22 F17 1.334(6) . ? C22 F16 1.335(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 O6 TB1 O2 121.69(10) . . ? O6 TB1 O5 78.55(10) . . ? O2 TB1 O5 138.36(10) . . ? O6 TB1 O7 72.01(10) . . ? O2 TB1 O7 147.42(10) . . ? O5 TB1 O7 69.88(10) . . ? O6 TB1 O4 72.75(10) . . ? O2 TB1 O4 79.20(10) . . ? O5 TB1 O4 72.88(10) . . ? O7 TB1 O4 132.59(10) . . ? O6 TB1 O1 143.45(10) . . ? O2 TB1 O1 89.22(10) . . ? O5 TB1 O1 90.97(10) . . ? O7 TB1 O1 71.51(10) . . ? O4 TB1 O1 137.48(10) . . ? O6 TB1 O3 137.25(10) . . ? O2 TB1 O3 69.98(10) . . ? O5 TB1 O3 71.62(10) . . ? O7 TB1 O3 122.33(10) . . ? O4 TB1 O3 69.66(10) . . ? O1 TB1 O3 67.93(10) . . ? O6 TB1 N6 92.51(11) . 4_565 ? O2 TB1 N6 78.42(11) . 4_565 ? O5 TB1 N6 140.92(10) . 4_565 ? O7 TB1 N6 71.17(10) . 4_565 ? O4 TB1 N6 140.75(9) . 4_565 ? O1 TB1 N6 73.78(10) . 4_565 ? O3 TB1 N6 129.78(11) . 4_565 ? C1 O1 TB1 140.0(3) . . ? C8 O2 TB1 134.0(3) . . ? C10 O3 TB1 131.6(3) . . ? C13 O4 TB1 134.0(3) . . ? C15 O5 TB1 133.9(3) . . ? C18 O6 TB1 134.6(3) . . ? C20 O7 TB1 133.7(3) . . ? C2 N1 N2 114.2(3) . . ? C1 N2 N1 123.2(3) . . ? C1 N2 C6 120.5(3) . . ? N1 N2 C6 116.3(3) . . ? C1 N3 N4 123.7(3) . . ? C1 N3 C7 120.9(3) . . ? N4 N3 C7 115.4(3) . . ? C2 N4 N3 113.9(3) . . ? C3 N5 C4 108.3(3) . . ? C3 N5 H5 125.9 . . ? C4 N5 H5 125.9 . . ? C3 N6 C5 104.3(3) . . ? C3 N6 TB1 128.9(3) . 4_566 ? C5 N6 TB1 126.8(3) . 4_566 ? O1 C1 N3 122.0(4) . . ? O1 C1 N2 121.7(4) . . ? N3 C1 N2 116.3(3) . . ? N1 C2 N4 128.8(4) . . ? N1 C2 C3 115.8(3) . . ? N4 C2 C3 115.4(3) . . ? N6 C3 N5 111.2(3) . . ? N6 C3 C2 124.2(4) . . ? N5 C3 C2 124.5(3) . . ? C5 C4 N5 105.4(4) . . ? C5 C4 H4 127.3 . . ? N5 C4 H4 127.3 . . ? C4 C5 N6 110.8(4) . . ? C4 C5 H5A 124.6 . . ? N6 C5 H5A 124.6 . . ? N2 C6 H6A 109.5 . . ? N2 C6 H6B 109.5 . . ? H6A C6 H6B 109.5 . . ? N2 C6 H6C 109.5 . . ? H6A C6 H6C 109.5 . . ? H6B C6 H6C 109.5 . . ? N3 C7 H7A 109.5 . . ? N3 C7 H7B 109.5 . . ? H7A C7 H7B 109.5 . . ? N3 C7 H7C 109.5 . . ? H7A C7 H7C 109.5 . . ? H7B C7 H7C 109.5 . . ? O2 C8 C9 128.3(4) . . ? O2 C8 C11 113.7(5) . . ? C9 C8 C11 117.9(5) . . ? C8 C9 C10 120.8(5) . . ? C8 C9 H9 119.6 . . ? C10 C9 H9 119.6 . . ? O3 C10 C9 127.6(4) . . ? O3 C10 C12 113.5(4) . . ? C9 C10 C12 118.9(5) . . ? F1 C11 F2 106.2(7) . . ? F1 C11 F3 106.4(6) . . ? F2 C11 F3 106.4(6) . . ? F1 C11 C8 111.6(6) . . ? F2 C11 C8 111.1(6) . . ? F3 C11 C8 114.7(6) . . ? F6 C12 F5 109.5(6) . . ? F6 C12 F4 106.4(5) . . ? F5 C12 F4 106.8(5) . . ? F6 C12 C10 113.1(5) . . ? F5 C12 C10 110.4(5) . . ? F4 C12 C10 110.4(5) . . ? O4 C13 C14 128.2(4) . . ? O4 C13 C16 114.3(4) . . ? C14 C13 C16 117.4(4) . . ? C13 C14 C15 122.4(4) . . ? C13 C14 H14 118.8 . . ? C15 C14 H14 118.8 . . ? O5 C15 C14 128.5(4) . . ? O5 C15 C17 114.3(4) . . ? C14 C15 C17 117.2(4) . . ? F9 C16 F7 108.9(5) . . ? F9 C16 F8 106.0(5) . . ? F7 C16 F8 103.6(5) . . ? F9 C16 C13 114.4(4) . . ? F7 C16 C13 113.0(4) . . ? F8 C16 C13 110.2(5) . . ? F11 C17 F12 111.1(6) . . ? F11 C17 F10 106.0(5) . . ? F12 C17 F10 102.0(5) . . ? F11 C17 C15 113.9(4) . . ? F12 C17 C15 110.3(4) . . ? F10 C17 C15 112.8(5) . . ? O6 C18 C19 127.7(4) . . ? O6 C18 C21 113.1(4) . . ? C19 C18 C21 119.1(4) . . ? C18 C19 C20 121.3(4) . . ? C18 C19 H19 119.3 . . ? C20 C19 H19 119.3 . . ? O7 C20 C19 128.0(4) . . ? O7 C20 C22 112.8(4) . . ? C19 C20 C22 119.1(4) . . ? F15 C21 F14 107.8(5) . . ? F15 C21 F13 107.1(4) . . ? F14 C21 F13 106.7(5) . . ? F15 C21 C18 112.1(4) . . ? F14 C21 C18 109.7(4) . . ? F13 C21 C18 113.1(5) . . ? F18 C22 F17 107.9(4) . . ? F18 C22 F16 106.5(5) . . ? F17 C22 F16 106.8(4) . . ? F18 C22 C20 111.6(4) . . ? F17 C22 C20 110.0(4) . . ? F16 C22 C20 113.8(4) . . ? _diffrn_measured_fraction_theta_max 0.942 _diffrn_reflns_theta_full 30.01 _diffrn_measured_fraction_theta_full 0.942 _refine_diff_density_max 1.561 _refine_diff_density_min -1.247 _refine_diff_density_rms 0.137 # Attachment 'CCDC6999836.cif' ######################################################################### data_ln488 _database_code_depnum_ccdc_archive 'CCDC 699836' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C22 H12 F18 N6 O7 Pr' _chemical_formula_sum 'C22 H12 F18 N6 O7 Pr' _chemical_formula_weight 955.29 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' F F 0.0171 0.0103 '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' 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 'P 21/c' _symmetry_space_group_name_Hall '-P 2ybc' _symmetry_Int_Tables_number 14 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 11.419(13) _cell_length_b 18.878(11) _cell_length_c 16.463(11) _cell_angle_alpha 90.00 _cell_angle_beta 107.99(7) _cell_angle_gamma 90.00 _cell_volume 3375(5) _cell_formula_units_Z 4 _cell_measurement_temperature 200(2) _cell_measurement_reflns_used 30 _cell_measurement_theta_min 4.2 _cell_measurement_theta_max 15.4 _exptl_crystal_description block _exptl_crystal_colour orange _exptl_crystal_size_max 0.15 _exptl_crystal_size_mid 0.11 _exptl_crystal_size_min 0.08 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.880 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1852 _exptl_absorpt_coefficient_mu 1.592 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.723 _exptl_absorpt_correction_T_max 0.880 _exptl_absorpt_process_details ; R.H. Blessing, Acta Cryst. (1995), A51, 33-38 ; _diffrn_ambient_temperature 200(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 KappaCCD _diffrn_measurement_method 'CCD rotation images, thick slices' _diffrn_detector_area_resol_mean 9 _diffrn_standards_number 0 _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% 0 _diffrn_reflns_number 17650 _diffrn_reflns_av_R_equivalents 0.0878 _diffrn_reflns_av_sigmaI/netI 0.1158 _diffrn_reflns_limit_h_min -11 _diffrn_reflns_limit_h_max 13 _diffrn_reflns_limit_k_min -19 _diffrn_reflns_limit_k_max 22 _diffrn_reflns_limit_l_min -19 _diffrn_reflns_limit_l_max 17 _diffrn_reflns_theta_min 1.69 _diffrn_reflns_theta_max 25.02 _reflns_number_total 5842 _reflns_number_gt 3321 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Collect (Nonius BV, 1997-2000)' _computing_cell_refinement 'Dirax/lsq (Duisenberg & Schreurs, 1989-2000)' _computing_data_reduction 'EvalCCD (Duisenberg & Schreurs 1990-2000)' _computing_structure_solution 'SIR92 (Giacovazzo et al, 1993)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'DIAMOND (Brandenburg, 1999)' _computing_publication_material 'WinGX publication routines (Farrugia, 1999)' _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^)+(0.0818P)^2^+5.4820P] 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 5842 _refine_ls_number_parameters 487 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.1352 _refine_ls_R_factor_gt 0.0608 _refine_ls_wR_factor_ref 0.1708 _refine_ls_wR_factor_gt 0.1323 _refine_ls_goodness_of_fit_ref 1.034 _refine_ls_restrained_S_all 1.034 _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 Pr Pr 0.14770(5) 0.23069(3) 0.87934(3) 0.0327(2) Uani 1 1 d . . . O1 O 0.0300(6) 0.2110(3) 0.9835(4) 0.0432(17) Uani 1 1 d . . . O2 O -0.0009(6) 0.3197(4) 0.8063(4) 0.0463(17) Uani 1 1 d . . . O3 O 0.1505(7) 0.3371(3) 0.9735(4) 0.0494(18) Uani 1 1 d . . . O4 O 0.2855(7) 0.3236(3) 0.8552(4) 0.0465(17) Uani 1 1 d . . . O5 O 0.3454(6) 0.2286(4) 0.9995(4) 0.0471(17) Uani 1 1 d . . . O6 O 0.2886(6) 0.1713(4) 0.8154(4) 0.0440(17) Uani 1 1 d . . . O7 O 0.1928(6) 0.1101(3) 0.9376(4) 0.0416(16) Uani 1 1 d . . . N1 N 0.0406(7) 0.2812(4) 1.1854(5) 0.0392(19) Uani 1 1 d . . . N2 N 0.0714(8) 0.2446(4) 1.1222(5) 0.041(2) Uani 1 1 d . . . N3 N -0.1057(8) 0.2845(4) 1.0197(5) 0.044(2) Uani 1 1 d . . . N4 N -0.1418(7) 0.3230(4) 1.0787(5) 0.040(2) Uani 1 1 d . . . N5 N -0.1899(7) 0.4071(4) 1.2073(5) 0.044(2) Uani 1 1 d . . . H5A H -0.2376 0.4190 1.1577 0.053 Uiso 1 1 calc R . . N6 N -0.0391(7) 0.3536(4) 1.3074(5) 0.0355(18) Uani 1 1 d . . . C1 C -0.0002(9) 0.2452(4) 1.0385(6) 0.036(2) Uani 1 1 d . . . C2 C -0.0637(9) 0.3179(5) 1.1582(6) 0.037(2) Uani 1 1 d . . . C3 C -0.0992(9) 0.3583(5) 1.2240(6) 0.037(2) Uani 1 1 d . . . C4 C -0.1923(10) 0.4343(5) 1.2845(7) 0.050(3) Uani 1 1 d . . . H4 H -0.2455 0.4686 1.2936 0.060 Uiso 1 1 calc R . . C5 C -0.0992(10) 0.4001(5) 1.3450(6) 0.045(3) Uani 1 1 d . . . H5 H -0.0795 0.4075 1.4035 0.054 Uiso 1 1 calc R . . C6 C -0.1917(11) 0.2850(7) 0.9331(7) 0.066(3) Uani 1 1 d . . . H6A H -0.2529 0.2489 0.9280 0.100 Uiso 1 1 calc R . . H6B H -0.1478 0.2759 0.8930 0.100 Uiso 1 1 calc R . . H6C H -0.2311 0.3304 0.9214 0.100 Uiso 1 1 calc R . . C7 C 0.1873(10) 0.2043(6) 1.1480(7) 0.058(3) Uani 1 1 d . . . H7A H 0.1762 0.1604 1.1173 0.087 Uiso 1 1 calc R . . H7B H 0.2107 0.1948 1.2082 0.087 Uiso 1 1 calc R . . H7C H 0.2508 0.2314 1.1355 0.087 Uiso 1 1 calc R . . C8 C -0.0090(10) 0.3869(7) 0.8112(7) 0.058(3) Uani 1 1 d . . . C9 C 0.0541(11) 0.4311(6) 0.8798(7) 0.057(3) Uani 1 1 d . . . H9 H 0.0480 0.4801 0.8740 0.068 Uiso 1 1 calc R . . C10 C 0.1261(10) 0.4007(6) 0.9571(7) 0.052(3) Uani 1 1 d . . . C11 C -0.0950(16) 0.4215(10) 0.7312(13) 0.100(5) Uani 1 1 d . . . C12 C 0.1841(15) 0.4526(6) 1.0328(10) 0.078(4) Uani 1 1 d . . . C13 C 0.3943(10) 0.3435(5) 0.8950(7) 0.045(3) Uani 1 1 d . . . C14 C 0.4765(10) 0.3172(6) 0.9696(7) 0.052(3) Uani 1 1 d . . . H14 H 0.5542 0.3376 0.9897 0.063 Uiso 1 1 calc R . . C15 C 0.4481(9) 0.2620(5) 1.0153(6) 0.044(2) Uani 1 1 d . . . C16 C 0.4400(11) 0.4092(6) 0.8542(8) 0.061(3) Uani 1 1 d . . . C17 C 0.5487(12) 0.2336(7) 1.0936(8) 0.066(3) Uani 1 1 d . . . C18 C 0.3562(9) 0.1182(6) 0.8321(6) 0.042(2) Uani 1 1 d . . . C19 C 0.3540(10) 0.0635(6) 0.8896(6) 0.050(3) Uani 1 1 d . . . H19 H 0.4083 0.0257 0.8955 0.060 Uiso 1 1 calc R . . C20 C 0.2722(10) 0.0641(5) 0.9383(6) 0.043(2) Uani 1 1 d . . . C21 C 0.4528(12) 0.1151(7) 0.7837(7) 0.064(3) Uani 1 1 d . . . C22 C 0.2803(12) 0.0039(6) 1.0027(7) 0.056(3) Uani 1 1 d . . . F1 F -0.0881(8) 0.4935(5) 0.7307(6) 0.113(3) Uani 1 1 d . . . F2 F -0.0812(16) 0.3998(7) 0.6618(7) 0.203(8) Uani 1 1 d . . . F3 F -0.2127(11) 0.4082(6) 0.7280(9) 0.173(6) Uani 1 1 d . . . F4 F 0.1535(9) 0.5191(4) 1.0166(6) 0.120(3) Uani 1 1 d . . . F5 F 0.3074(9) 0.4484(4) 1.0536(6) 0.107(3) Uani 1 1 d . . . F6 F 0.1529(9) 0.4336(4) 1.1020(5) 0.104(3) Uani 1 1 d . . . F7 F 0.5569(7) 0.4180(4) 0.8763(6) 0.114(3) Uani 1 1 d . . . F8 F 0.3902(8) 0.4676(4) 0.8723(6) 0.104(3) Uani 1 1 d . . . F9 F 0.3971(9) 0.4067(4) 0.7682(5) 0.104(3) Uani 1 1 d . . . F10 F 0.5055(8) 0.1961(6) 1.1441(6) 0.155(5) Uani 1 1 d . . . F11 F 0.6129(7) 0.2852(5) 1.1416(5) 0.093(2) Uani 1 1 d . . . F12 F 0.6302(9) 0.1964(5) 1.0701(6) 0.131(4) Uani 1 1 d . . . F13 F 0.4856(8) 0.0491(5) 0.7707(5) 0.105(3) Uani 1 1 d . . . F14 F 0.4100(7) 0.1448(4) 0.7071(5) 0.092(2) Uani 1 1 d . . . F15 F 0.5527(8) 0.1481(5) 0.8273(5) 0.111(3) Uani 1 1 d . . . F16 F 0.1678(8) -0.0191(4) 0.9981(5) 0.092(2) Uani 1 1 d . . . F17 F 0.3350(9) 0.0266(4) 1.0816(5) 0.102(3) Uani 1 1 d . . . F18 F 0.3430(8) -0.0519(4) 0.9914(5) 0.089(2) 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 Pr 0.0361(3) 0.0361(3) 0.0300(3) -0.0002(2) 0.0161(2) -0.0013(3) O1 0.050(4) 0.059(5) 0.028(4) -0.014(3) 0.023(3) 0.000(3) O2 0.046(4) 0.043(5) 0.051(4) -0.002(3) 0.016(3) 0.003(3) O3 0.064(5) 0.035(4) 0.052(5) 0.001(3) 0.022(4) 0.006(3) O4 0.048(5) 0.049(4) 0.040(4) 0.009(3) 0.009(4) -0.005(3) O5 0.045(4) 0.056(4) 0.037(4) 0.001(3) 0.009(3) -0.002(4) O6 0.042(4) 0.054(5) 0.041(4) 0.004(3) 0.020(3) 0.002(3) O7 0.046(4) 0.037(4) 0.044(4) 0.006(3) 0.017(3) 0.004(3) N1 0.043(5) 0.051(5) 0.029(4) -0.009(4) 0.019(4) 0.000(4) N2 0.046(5) 0.055(5) 0.027(4) 0.001(3) 0.020(4) 0.010(4) N3 0.043(5) 0.069(6) 0.023(4) -0.004(4) 0.012(4) 0.009(4) N4 0.033(5) 0.060(6) 0.029(5) 0.000(4) 0.011(4) 0.003(4) N5 0.046(5) 0.054(5) 0.034(5) -0.003(4) 0.013(4) 0.015(4) N6 0.046(5) 0.037(4) 0.029(4) 0.001(3) 0.019(4) 0.006(4) C1 0.049(6) 0.037(6) 0.030(5) 0.006(4) 0.022(5) -0.002(4) C2 0.044(6) 0.037(6) 0.036(6) -0.001(4) 0.023(5) -0.001(5) C3 0.038(6) 0.039(6) 0.038(6) 0.005(4) 0.018(5) 0.006(4) C4 0.054(7) 0.048(7) 0.057(7) -0.004(5) 0.031(6) 0.008(5) C5 0.056(7) 0.049(6) 0.035(6) -0.014(5) 0.019(5) 0.010(5) C6 0.051(7) 0.110(11) 0.041(7) -0.018(6) 0.019(6) 0.009(7) C7 0.058(8) 0.080(8) 0.040(6) 0.003(6) 0.022(6) 0.022(6) C8 0.031(6) 0.087(10) 0.055(8) 0.008(7) 0.010(6) 0.011(6) C9 0.064(8) 0.043(7) 0.061(8) 0.013(6) 0.016(7) 0.009(6) C10 0.055(7) 0.057(8) 0.052(7) -0.009(6) 0.026(6) -0.002(6) C11 0.069(11) 0.110(14) 0.122(16) 0.033(11) 0.031(11) 0.009(9) C12 0.093(12) 0.035(8) 0.103(12) -0.023(7) 0.025(10) -0.005(7) C13 0.045(7) 0.046(6) 0.048(7) 0.000(5) 0.021(6) 0.012(5) C14 0.043(7) 0.062(7) 0.055(7) -0.007(6) 0.021(6) -0.016(5) C15 0.034(6) 0.055(7) 0.042(6) -0.001(5) 0.012(5) 0.005(5) C16 0.047(8) 0.061(8) 0.071(9) 0.007(6) 0.015(7) -0.013(6) C17 0.063(8) 0.061(8) 0.065(8) 0.011(7) 0.005(7) 0.003(7) C18 0.038(6) 0.061(7) 0.030(6) -0.006(5) 0.017(5) 0.005(5) C19 0.054(7) 0.059(7) 0.039(6) 0.005(5) 0.018(5) 0.011(5) C20 0.056(7) 0.039(6) 0.034(6) 0.000(4) 0.014(5) 0.003(5) C21 0.071(9) 0.087(10) 0.040(7) -0.010(6) 0.026(7) 0.005(7) C22 0.067(8) 0.049(7) 0.054(8) 0.008(5) 0.022(7) 0.007(6) F1 0.106(7) 0.076(6) 0.139(8) 0.045(5) 0.012(6) 0.014(5) F2 0.33(2) 0.197(13) 0.058(6) 0.039(7) 0.025(9) 0.144(13) F3 0.102(9) 0.147(10) 0.206(13) 0.085(9) -0.044(8) -0.003(7) F4 0.165(9) 0.048(5) 0.133(8) -0.027(5) 0.026(7) 0.001(5) F5 0.088(7) 0.091(6) 0.129(8) -0.053(5) 0.016(6) -0.029(5) F6 0.142(8) 0.103(6) 0.072(5) -0.038(5) 0.039(6) 0.009(5) F7 0.051(5) 0.109(6) 0.169(9) 0.065(6) 0.014(5) -0.025(4) F8 0.126(7) 0.056(5) 0.133(8) 0.017(4) 0.045(6) 0.008(5) F9 0.136(8) 0.102(6) 0.074(6) 0.019(4) 0.035(5) -0.050(5) F10 0.092(7) 0.219(11) 0.120(8) 0.119(8) -0.019(6) -0.043(7) F11 0.074(5) 0.129(7) 0.063(5) -0.009(4) 0.002(4) -0.011(5) F12 0.129(8) 0.141(8) 0.101(7) -0.009(6) 0.001(6) 0.088(7) F13 0.123(7) 0.114(7) 0.107(7) 0.010(5) 0.081(6) 0.051(5) F14 0.100(6) 0.129(6) 0.070(5) 0.023(4) 0.060(5) 0.040(5) F15 0.065(5) 0.192(9) 0.092(6) -0.039(6) 0.046(5) -0.032(6) F16 0.090(6) 0.093(6) 0.108(6) 0.050(5) 0.051(5) 0.003(4) F17 0.168(9) 0.083(5) 0.041(4) 0.010(4) 0.010(5) 0.015(5) F18 0.117(7) 0.063(5) 0.090(6) 0.023(4) 0.037(5) 0.028(4) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag Pr O2 2.427(7) . ? Pr O6 2.449(7) . ? Pr O7 2.462(6) . ? Pr O4 2.470(7) . ? Pr O5 2.501(7) . ? Pr O1 2.511(6) . ? Pr O3 2.532(7) . ? Pr N6 2.631(8) 4_565 ? O1 C1 1.244(10) . ? O2 C8 1.276(13) . ? O3 C10 1.242(12) . ? O4 C13 1.269(12) . ? O5 C15 1.285(12) . ? O6 C18 1.244(11) . ? O7 C20 1.252(11) . ? N1 C2 1.331(12) . ? N1 N2 1.381(10) . ? N2 C1 1.368(12) . ? N2 C7 1.472(13) . ? N3 C1 1.366(12) . ? N3 N4 1.374(10) . ? N3 C6 1.461(13) . ? N4 C2 1.341(12) . ? N5 C3 1.349(12) . ? N5 C4 1.378(12) . ? N5 H5A 0.8600 . ? N6 C3 1.336(11) . ? N6 C5 1.374(11) . ? N6 Pr 2.631(8) 4_566 ? C2 C3 1.479(12) . ? C4 C5 1.373(14) . ? C4 H4 0.9300 . ? C5 H5 0.9300 . ? C6 H6A 0.9600 . ? C6 H6B 0.9600 . ? C6 H6C 0.9600 . ? C7 H7A 0.9600 . ? C7 H7B 0.9600 . ? C7 H7C 0.9600 . ? C8 C9 1.410(16) . ? C8 C11 1.525(19) . ? C9 C10 1.406(15) . ? C9 H9 0.9300 . ? C10 C12 1.564(17) . ? C11 F2 1.268(19) . ? C11 F3 1.351(18) . ? C11 F1 1.363(18) . ? C12 F4 1.309(14) . ? C12 F6 1.342(16) . ? C12 F5 1.346(16) . ? C13 C14 1.387(15) . ? C13 C16 1.573(15) . ? C14 C15 1.381(14) . ? C14 H14 0.9300 . ? C15 C17 1.534(16) . ? C16 F7 1.282(13) . ? C16 F8 1.316(14) . ? C16 F9 1.348(14) . ? C17 F10 1.299(14) . ? C17 F12 1.315(15) . ? C17 F11 1.325(14) . ? C18 C19 1.406(14) . ? C18 C21 1.548(14) . ? C19 C20 1.408(13) . ? C19 H19 0.9300 . ? C20 C22 1.535(14) . ? C21 F15 1.304(14) . ? C21 F14 1.327(13) . ? C21 F13 1.338(14) . ? C22 F18 1.319(12) . ? C22 F17 1.326(13) . ? C22 F16 1.337(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 Pr O6 123.8(2) . . ? O2 Pr O7 149.7(2) . . ? O6 Pr O7 70.0(2) . . ? O2 Pr O4 79.1(2) . . ? O6 Pr O4 73.7(2) . . ? O7 Pr O4 130.7(2) . . ? O2 Pr O5 136.5(2) . . ? O6 Pr O5 77.3(2) . . ? O7 Pr O5 69.4(2) . . ? O4 Pr O5 71.0(2) . . ? O2 Pr O1 90.0(2) . . ? O6 Pr O1 141.9(2) . . ? O7 Pr O1 71.9(2) . . ? O4 Pr O1 135.8(2) . . ? O5 Pr O1 90.0(2) . . ? O2 Pr O3 68.2(2) . . ? O6 Pr O3 137.7(2) . . ? O7 Pr O3 122.3(2) . . ? O4 Pr O3 69.3(2) . . ? O5 Pr O3 72.0(2) . . ? O1 Pr O3 66.9(2) . . ? O2 Pr N6 81.4(2) . 4_565 ? O6 Pr N6 94.5(2) . 4_565 ? O7 Pr N6 70.1(2) . 4_565 ? O4 Pr N6 145.6(2) . 4_565 ? O5 Pr N6 139.0(2) . 4_565 ? O1 Pr N6 71.8(2) . 4_565 ? O3 Pr N6 127.6(2) . 4_565 ? C1 O1 Pr 138.4(6) . . ? C8 O2 Pr 135.3(7) . . ? C10 O3 Pr 132.4(6) . . ? C13 O4 Pr 134.3(6) . . ? C15 O5 Pr 134.2(6) . . ? C18 O6 Pr 136.0(6) . . ? C20 O7 Pr 135.2(6) . . ? C2 N1 N2 114.7(8) . . ? C1 N2 N1 122.9(8) . . ? C1 N2 C7 120.0(7) . . ? N1 N2 C7 117.1(8) . . ? C1 N3 N4 124.3(8) . . ? C1 N3 C6 120.3(8) . . ? N4 N3 C6 115.4(8) . . ? C2 N4 N3 113.5(7) . . ? C3 N5 C4 107.5(8) . . ? C3 N5 H5A 126.3 . . ? C4 N5 H5A 126.3 . . ? C3 N6 C5 104.5(8) . . ? C3 N6 Pr 126.2(6) . 4_566 ? C5 N6 Pr 129.2(6) . 4_566 ? O1 C1 N3 122.7(9) . . ? O1 C1 N2 121.0(9) . . ? N3 C1 N2 116.3(8) . . ? N1 C2 N4 128.4(8) . . ? N1 C2 C3 116.3(8) . . ? N4 C2 C3 115.4(8) . . ? N6 C3 N5 111.9(8) . . ? N6 C3 C2 123.2(8) . . ? N5 C3 C2 124.8(9) . . ? C5 C4 N5 105.2(8) . . ? C5 C4 H4 127.4 . . ? N5 C4 H4 127.4 . . ? C4 C5 N6 110.9(8) . . ? C4 C5 H5 124.5 . . ? N6 C5 H5 124.5 . . ? N3 C6 H6A 109.5 . . ? N3 C6 H6B 109.5 . . ? H6A C6 H6B 109.5 . . ? N3 C6 H6C 109.5 . . ? H6A C6 H6C 109.5 . . ? H6B C6 H6C 109.5 . . ? N2 C7 H7A 109.5 . . ? N2 C7 H7B 109.5 . . ? H7A C7 H7B 109.5 . . ? N2 C7 H7C 109.5 . . ? H7A C7 H7C 109.5 . . ? H7B C7 H7C 109.5 . . ? O2 C8 C9 127.5(10) . . ? O2 C8 C11 114.3(12) . . ? C9 C8 C11 118.2(13) . . ? C10 C9 C8 119.7(11) . . ? C10 C9 H9 120.2 . . ? C8 C9 H9 120.2 . . ? O3 C10 C9 128.3(10) . . ? O3 C10 C12 114.9(10) . . ? C9 C10 C12 116.8(11) . . ? F2 C11 F3 107.7(19) . . ? F2 C11 F1 107.0(14) . . ? F3 C11 F1 104.1(13) . . ? F2 C11 C8 114.4(14) . . ? F3 C11 C8 108.8(13) . . ? F1 C11 C8 114.1(15) . . ? F4 C12 F6 107.8(12) . . ? F4 C12 F5 107.5(12) . . ? F6 C12 F5 107.4(13) . . ? F4 C12 C10 114.7(12) . . ? F6 C12 C10 110.6(11) . . ? F5 C12 C10 108.5(11) . . ? O4 C13 C14 129.6(10) . . ? O4 C13 C16 114.4(9) . . ? C14 C13 C16 115.9(10) . . ? C15 C14 C13 123.0(10) . . ? C15 C14 H14 118.5 . . ? C13 C14 H14 118.5 . . ? O5 C15 C14 127.8(10) . . ? O5 C15 C17 113.5(9) . . ? C14 C15 C17 118.8(10) . . ? F7 C16 F8 108.2(11) . . ? F7 C16 F9 108.1(11) . . ? F8 C16 F9 103.0(10) . . ? F7 C16 C13 115.7(10) . . ? F8 C16 C13 109.9(10) . . ? F9 C16 C13 111.1(9) . . ? F10 C17 F12 110.0(13) . . ? F10 C17 F11 105.5(12) . . ? F12 C17 F11 104.8(11) . . ? F10 C17 C15 113.2(11) . . ? F12 C17 C15 110.7(10) . . ? F11 C17 C15 112.1(10) . . ? O6 C18 C19 127.0(9) . . ? O6 C18 C21 114.1(9) . . ? C19 C18 C21 118.8(10) . . ? C18 C19 C20 122.1(9) . . ? C18 C19 H19 119.0 . . ? C20 C19 H19 119.0 . . ? O7 C20 C19 127.2(9) . . ? O7 C20 C22 114.2(9) . . ? C19 C20 C22 118.6(9) . . ? F15 C21 F14 108.9(11) . . ? F15 C21 F13 107.0(11) . . ? F14 C21 F13 106.3(9) . . ? F15 C21 C18 109.9(9) . . ? F14 C21 C18 111.2(10) . . ? F13 C21 C18 113.3(10) . . ? F18 C22 F17 106.5(10) . . ? F18 C22 F16 106.6(10) . . ? F17 C22 F16 108.3(10) . . ? F18 C22 C20 114.5(9) . . ? F17 C22 C20 110.3(9) . . ? F16 C22 C20 110.4(9) . . ? _diffrn_measured_fraction_theta_max 0.980 _diffrn_reflns_theta_full 25.02 _diffrn_measured_fraction_theta_full 0.980 _refine_diff_density_max 1.985 _refine_diff_density_min -1.262 _refine_diff_density_rms 0.151 # Attachment 'CCDC6999837.cif' ######################################################################### data_ln562 _database_code_depnum_ccdc_archive 'CCDC 699837' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C22 H12 Dy F18 N6 O7' _chemical_formula_sum 'C22 H12 Dy F18 N6 O7' _chemical_formula_weight 976.88 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Dy Dy -0.1892 4.4098 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M 'P 21/c' _symmetry_space_group_name_Hall '-P 2ybc' _symmetry_Int_Tables_number 14 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 11.3474(13) _cell_length_b 18.303(3) _cell_length_c 16.729(2) _cell_angle_alpha 90.00 _cell_angle_beta 107.540(9) _cell_angle_gamma 90.00 _cell_volume 3312.9(8) _cell_formula_units_Z 4 _cell_measurement_temperature 200(2) _cell_measurement_reflns_used 219 _cell_measurement_theta_min 4.4 _cell_measurement_theta_max 21.1 _exptl_crystal_description plate-like _exptl_crystal_colour orange _exptl_crystal_size_max 0.33 _exptl_crystal_size_mid 0.21 _exptl_crystal_size_min 0.06 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.959 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1880 _exptl_absorpt_coefficient_mu 2.407 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.590 _exptl_absorpt_correction_T_max 0.866 _exptl_absorpt_process_details ; R.H. Blessing, Acta Cryst. (1995), A51, 33-38 ; _diffrn_ambient_temperature 200(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 KappaCCD _diffrn_measurement_method 'CCD rotation images, thick slices' _diffrn_detector_area_resol_mean 9 _diffrn_standards_number 0 _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% 0 _diffrn_reflns_number 37805 _diffrn_reflns_av_R_equivalents 0.0453 _diffrn_reflns_av_sigmaI/netI 0.0538 _diffrn_reflns_limit_h_min -14 _diffrn_reflns_limit_h_max 15 _diffrn_reflns_limit_k_min -25 _diffrn_reflns_limit_k_max 25 _diffrn_reflns_limit_l_min -23 _diffrn_reflns_limit_l_max 23 _diffrn_reflns_theta_min 2.79 _diffrn_reflns_theta_max 30.03 _reflns_number_total 9397 _reflns_number_gt 6363 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Collect (Nonius BV, 1997-2000)' _computing_cell_refinement 'Dirax/lsq (Duisenberg & Schreurs, 1989-2000)' _computing_data_reduction 'EvalCCD (Duisenberg & Schreurs 1990-2000)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1997)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'DIAMOND (Brandenburg, 1999)' _computing_publication_material 'WinGX publication routines (Farrugia, 1999)' _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^)+(0.0419P)^2^+4.6724P] 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 9397 _refine_ls_number_parameters 489 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0773 _refine_ls_R_factor_gt 0.0363 _refine_ls_wR_factor_ref 0.0990 _refine_ls_wR_factor_gt 0.0807 _refine_ls_goodness_of_fit_ref 1.055 _refine_ls_restrained_S_all 1.055 _refine_ls_shift/su_max 0.004 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group Dy1 Dy 0.153125(16) 0.271620(10) 0.384940(11) 0.02521(6) Uani 1 1 d . . . O1 O 0.0357(3) 0.28912(16) 0.48094(17) 0.0356(7) Uani 1 1 d . . . O2 O 0.0053(3) 0.18608(17) 0.31269(17) 0.0368(6) Uani 1 1 d . . . O3 O 0.1624(3) 0.16423(16) 0.47475(18) 0.0395(7) Uani 1 1 d . . . O4 O 0.2821(3) 0.18068(17) 0.35264(18) 0.0368(7) Uani 1 1 d . . . O5 O 0.3427(3) 0.27528(16) 0.49535(18) 0.0364(7) Uani 1 1 d . . . O6 O 0.2807(3) 0.33015(17) 0.31856(18) 0.0376(7) Uani 1 1 d . . . O7 O 0.1891(3) 0.39185(16) 0.44003(18) 0.0356(7) Uani 1 1 d . . . N1 N 0.0514(3) 0.2221(2) 0.68402(19) 0.0331(8) Uani 1 1 d . . . N2 N 0.0803(3) 0.2578(2) 0.6197(2) 0.0347(8) Uani 1 1 d . . . N3 N -0.1005(3) 0.2170(2) 0.5215(2) 0.0351(8) Uani 1 1 d . . . N4 N -0.1355(3) 0.1799(2) 0.58229(19) 0.0352(8) Uani 1 1 d . . . N5 N -0.1849(3) 0.0982(2) 0.7102(2) 0.0387(9) Uani 1 1 d . . . H5 H -0.2360 0.0883 0.6619 0.046 Uiso 1 1 calc R . . N6 N -0.0276(3) 0.14900(19) 0.80748(19) 0.0301(7) Uani 1 1 d . . . C1 C 0.0066(4) 0.2561(2) 0.5374(2) 0.0306(9) Uani 1 1 d . . . C2 C -0.0555(3) 0.1855(2) 0.6589(2) 0.0288(8) Uani 1 1 d . . . C3 C -0.0882(4) 0.1447(2) 0.7259(2) 0.0294(8) Uani 1 1 d . . . C4 C -0.1864(4) 0.0692(3) 0.7863(3) 0.0423(11) Uani 1 1 d . . . H4 H -0.2418 0.0351 0.7954 0.051 Uiso 1 1 calc R . . C5 C -0.0902(4) 0.1011(2) 0.8451(3) 0.0361(10) Uani 1 1 d . . . H5A H -0.0691 0.0920 0.9024 0.043 Uiso 1 1 calc R . . C6 C 0.1958(5) 0.2996(3) 0.6438(3) 0.0560(14) Uani 1 1 d . . . H6A H 0.2645 0.2668 0.6522 0.084 Uiso 1 1 calc R . . H6B H 0.2030 0.3257 0.6949 0.084 Uiso 1 1 calc R . . H6C H 0.1957 0.3337 0.6002 0.084 Uiso 1 1 calc R . . C7 C -0.1892(4) 0.2147(3) 0.4369(3) 0.0520(14) Uani 1 1 d . . . H7A H -0.2530 0.2502 0.4328 0.078 Uiso 1 1 calc R . . H7B H -0.2252 0.1669 0.4264 0.078 Uiso 1 1 calc R . . H7C H -0.1472 0.2256 0.3963 0.078 Uiso 1 1 calc R . . C8 C -0.0041(4) 0.1177(3) 0.3160(3) 0.0427(11) Uani 1 1 d . . . C9 C 0.0568(5) 0.0708(3) 0.3807(3) 0.0501(12) Uani 1 1 d . . . H9 H 0.0473 0.0205 0.3735 0.060 Uiso 1 1 calc R . . C10 C 0.1332(4) 0.0996(3) 0.4575(3) 0.0435(11) Uani 1 1 d . . . C11 C -0.0983(6) 0.0843(4) 0.2380(5) 0.0767(19) Uani 1 1 d . . . C12 C 0.1891(7) 0.0460(3) 0.5304(4) 0.0708(17) Uani 1 1 d . . . C13 C 0.3901(4) 0.1585(2) 0.3897(3) 0.0380(10) Uani 1 1 d . . . C14 C 0.4730(4) 0.1843(3) 0.4639(3) 0.0458(11) Uani 1 1 d . . . H14 H 0.5512 0.1634 0.4830 0.055 Uiso 1 1 calc R . . C15 C 0.4423(4) 0.2409(3) 0.5107(3) 0.0395(10) Uani 1 1 d . . . C16 C 0.4323(5) 0.0928(3) 0.3463(4) 0.0540(13) Uani 1 1 d . . . C17 C 0.5442(5) 0.2660(3) 0.5901(3) 0.0553(14) Uani 1 1 d . . . C18 C 0.3490(4) 0.3863(3) 0.3343(3) 0.0370(10) Uani 1 1 d . . . C19 C 0.3492(4) 0.4417(3) 0.3907(3) 0.0422(11) Uani 1 1 d . . . H19 H 0.4040 0.4805 0.3964 0.051 Uiso 1 1 calc R . . C20 C 0.2675(4) 0.4401(2) 0.4398(2) 0.0334(9) Uani 1 1 d . . . C21 C 0.4441(5) 0.3891(4) 0.2849(3) 0.0583(15) Uani 1 1 d . . . C22 C 0.2720(5) 0.5022(3) 0.5017(3) 0.0516(13) Uani 1 1 d . . . F1 F -0.0866(7) 0.1111(3) 0.1688(3) 0.168(3) Uani 1 1 d . . . F2 F -0.2119(4) 0.0996(3) 0.2380(4) 0.147(2) Uani 1 1 d . . . F3 F -0.0917(4) 0.0127(2) 0.2328(3) 0.1056(15) Uani 1 1 d . . . F4 F 0.1544(4) 0.0645(2) 0.5978(2) 0.0946(13) Uani 1 1 d . . . F5 F 0.3125(4) 0.0492(2) 0.5535(3) 0.0977(13) Uani 1 1 d . . . F6 F 0.1542(5) -0.0229(2) 0.5132(3) 0.1182(17) Uani 1 1 d . . . F7 F 0.3878(4) 0.0939(2) 0.2646(2) 0.1012(15) Uani 1 1 d . . . F8 F 0.3890(5) 0.0306(2) 0.3691(3) 0.1063(14) Uani 1 1 d . . . F9 F 0.5521(3) 0.0842(2) 0.3680(3) 0.0950(14) Uani 1 1 d . . . F10 F 0.6005(4) 0.2093(3) 0.6380(2) 0.0985(14) Uani 1 1 d . . . F11 F 0.5052(4) 0.3070(4) 0.6389(3) 0.173(3) Uani 1 1 d . . . F12 F 0.6366(4) 0.2969(3) 0.5709(3) 0.1066(15) Uani 1 1 d . . . F13 F 0.4805(4) 0.4565(2) 0.2744(3) 0.1031(15) Uani 1 1 d . . . F14 F 0.5446(3) 0.3522(3) 0.3253(3) 0.1022(15) Uani 1 1 d . . . F15 F 0.3995(3) 0.3593(2) 0.2092(2) 0.0863(12) Uani 1 1 d . . . F16 F 0.3409(4) 0.55860(19) 0.4941(2) 0.0864(12) Uani 1 1 d . . . F17 F 0.3174(4) 0.4783(2) 0.5803(2) 0.0974(14) Uani 1 1 d . . . F18 F 0.1589(3) 0.5284(2) 0.4930(2) 0.0841(11) 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 Dy1 0.02487(10) 0.02705(10) 0.02533(9) 0.00048(8) 0.01003(7) 0.00010(8) O1 0.0397(17) 0.0451(18) 0.0271(14) 0.0063(12) 0.0177(13) -0.0023(13) O2 0.0341(16) 0.0356(17) 0.0380(16) -0.0022(13) 0.0070(13) -0.0015(13) O3 0.0457(18) 0.0323(17) 0.0387(16) 0.0048(13) 0.0100(14) -0.0037(13) O4 0.0312(15) 0.0388(17) 0.0388(16) -0.0057(13) 0.0083(13) 0.0044(13) O5 0.0323(16) 0.0405(17) 0.0338(15) -0.0016(13) 0.0062(12) 0.0005(13) O6 0.0394(17) 0.0423(18) 0.0366(16) -0.0022(13) 0.0196(13) -0.0052(14) O7 0.0403(17) 0.0326(16) 0.0381(16) -0.0035(13) 0.0184(13) -0.0020(13) N1 0.0333(18) 0.044(2) 0.0221(15) 0.0026(14) 0.0089(14) -0.0070(16) N2 0.035(2) 0.048(2) 0.0236(16) -0.0003(15) 0.0123(14) -0.0118(16) N3 0.0287(18) 0.055(2) 0.0208(15) 0.0029(15) 0.0071(14) -0.0088(16) N4 0.0331(18) 0.052(2) 0.0228(16) -0.0009(15) 0.0111(14) -0.0106(17) N5 0.037(2) 0.045(2) 0.0319(18) 0.0030(16) 0.0079(16) -0.0140(17) N6 0.0344(18) 0.0356(19) 0.0221(15) 0.0029(13) 0.0110(14) -0.0056(15) C1 0.033(2) 0.036(2) 0.0252(19) -0.0001(16) 0.0131(17) 0.0008(17) C2 0.028(2) 0.036(2) 0.0241(18) -0.0025(16) 0.0111(15) -0.0033(17) C3 0.031(2) 0.032(2) 0.0255(19) -0.0009(16) 0.0092(16) -0.0032(17) C4 0.048(3) 0.044(3) 0.039(2) 0.003(2) 0.018(2) -0.015(2) C5 0.044(2) 0.037(2) 0.029(2) 0.0063(17) 0.0149(19) -0.0064(19) C6 0.055(3) 0.083(4) 0.032(2) -0.001(2) 0.016(2) -0.033(3) C7 0.033(2) 0.091(4) 0.027(2) 0.012(2) 0.0011(19) -0.007(2) C8 0.035(2) 0.042(3) 0.049(3) -0.009(2) 0.010(2) -0.005(2) C9 0.054(3) 0.027(2) 0.069(3) 0.000(2) 0.018(3) -0.008(2) C10 0.048(3) 0.033(3) 0.051(3) 0.012(2) 0.017(2) -0.001(2) C11 0.070(4) 0.066(4) 0.082(5) -0.034(4) 0.005(4) -0.021(3) C12 0.084(5) 0.041(3) 0.080(4) 0.020(3) 0.013(4) 0.001(3) C13 0.032(2) 0.039(3) 0.044(2) -0.0009(19) 0.014(2) 0.0043(18) C14 0.030(2) 0.054(3) 0.049(3) -0.005(2) 0.005(2) 0.009(2) C15 0.029(2) 0.052(3) 0.036(2) 0.003(2) 0.0070(18) -0.003(2) C16 0.049(3) 0.050(3) 0.060(3) -0.003(3) 0.011(3) 0.014(2) C17 0.033(3) 0.081(4) 0.044(3) -0.005(3) 0.000(2) 0.003(3) C18 0.032(2) 0.050(3) 0.031(2) 0.0078(19) 0.0123(18) -0.003(2) C19 0.042(3) 0.042(3) 0.045(2) 0.001(2) 0.016(2) -0.013(2) C20 0.035(2) 0.030(2) 0.032(2) 0.0024(17) 0.0054(18) 0.0011(18) C21 0.056(3) 0.081(4) 0.049(3) -0.004(3) 0.031(3) -0.015(3) C22 0.066(4) 0.042(3) 0.048(3) -0.010(2) 0.018(3) -0.011(3) F1 0.259(7) 0.160(5) 0.051(3) -0.030(3) -0.004(3) -0.104(5) F2 0.059(3) 0.158(5) 0.181(5) -0.080(4) -0.030(3) 0.001(3) F3 0.099(3) 0.065(3) 0.127(4) -0.050(2) -0.005(3) -0.014(2) F4 0.122(3) 0.096(3) 0.068(2) 0.034(2) 0.032(2) -0.009(3) F5 0.082(3) 0.090(3) 0.109(3) 0.040(3) 0.010(2) 0.035(2) F6 0.175(5) 0.039(2) 0.115(3) 0.028(2) 0.005(3) -0.002(2) F7 0.126(3) 0.111(3) 0.059(2) -0.020(2) 0.016(2) 0.071(3) F8 0.142(4) 0.048(2) 0.141(4) -0.020(2) 0.062(3) -0.007(2) F9 0.048(2) 0.097(3) 0.129(3) -0.051(3) 0.010(2) 0.0253(19) F10 0.085(3) 0.133(4) 0.057(2) 0.013(2) -0.010(2) 0.001(3) F11 0.064(3) 0.278(7) 0.131(4) -0.152(5) -0.039(3) 0.053(4) F12 0.087(3) 0.135(4) 0.083(3) -0.013(3) 0.001(2) -0.065(3) F13 0.131(4) 0.096(3) 0.116(3) -0.004(2) 0.088(3) -0.052(3) F14 0.054(2) 0.160(4) 0.107(3) 0.026(3) 0.045(2) 0.027(2) F15 0.089(3) 0.131(3) 0.056(2) -0.023(2) 0.0475(19) -0.035(2) F16 0.115(3) 0.048(2) 0.105(3) -0.0269(19) 0.047(2) -0.036(2) F17 0.172(4) 0.070(3) 0.0349(17) -0.0135(17) 0.007(2) -0.013(3) F18 0.082(3) 0.086(3) 0.091(3) -0.042(2) 0.038(2) 0.009(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 Dy1 O6 2.333(3) . ? Dy1 O2 2.346(3) . ? Dy1 O7 2.373(3) . ? Dy1 O5 2.377(3) . ? Dy1 O4 2.384(3) . ? Dy1 O1 2.397(3) . ? Dy1 O3 2.457(3) . ? Dy1 N6 2.529(3) 4_565 ? O1 C1 1.246(5) . ? O2 C8 1.259(5) . ? O3 C10 1.239(5) . ? O4 C13 1.262(5) . ? O5 C15 1.251(5) . ? O6 C18 1.266(5) . ? O7 C20 1.254(5) . ? N1 C2 1.338(5) . ? N1 N2 1.380(4) . ? N2 C1 1.379(5) . ? N2 C6 1.466(6) . ? N3 C1 1.366(5) . ? N3 N4 1.378(4) . ? N3 C7 1.469(5) . ? N4 C2 1.333(5) . ? N5 C3 1.352(5) . ? N5 C4 1.384(5) . ? N5 H5 0.8600 . ? N6 C3 1.332(5) . ? N6 C5 1.392(5) . ? N6 Dy1 2.529(3) 4_566 ? C2 C3 1.484(5) . ? C4 C5 1.361(6) . ? C4 H4 0.9300 . ? C5 H5A 0.9300 . ? C6 H6A 0.9600 . ? C6 H6B 0.9600 . ? C6 H6C 0.9600 . ? C7 H7A 0.9600 . ? C7 H7B 0.9600 . ? C7 H7C 0.9600 . ? C8 C9 1.392(7) . ? C8 C11 1.542(7) . ? C9 C10 1.418(7) . ? C9 H9 0.9300 . ? C10 C12 1.544(7) . ? C11 F1 1.300(9) . ? C11 F3 1.318(7) . ? C11 F2 1.319(8) . ? C12 F6 1.327(7) . ? C12 F5 1.337(7) . ? C12 F4 1.344(8) . ? C13 C14 1.394(6) . ? C13 C16 1.553(7) . ? C14 C15 1.404(7) . ? C14 H14 0.9300 . ? C15 C17 1.544(7) . ? C16 F7 1.306(6) . ? C16 F9 1.306(6) . ? C16 F8 1.341(7) . ? C17 F11 1.281(7) . ? C17 F12 1.315(7) . ? C17 F10 1.348(7) . ? C18 C19 1.385(6) . ? C18 C21 1.545(6) . ? C19 C20 1.411(6) . ? C19 H19 0.9300 . ? C20 C22 1.528(6) . ? C21 F14 1.322(7) . ? C21 F15 1.331(6) . ? C21 F13 1.330(7) . ? C22 F16 1.325(6) . ? C22 F17 1.333(6) . ? C22 F18 1.336(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 O6 Dy1 O2 120.73(10) . . ? O6 Dy1 O7 72.55(10) . . ? O2 Dy1 O7 146.26(10) . . ? O6 Dy1 O5 79.10(10) . . ? O2 Dy1 O5 139.32(10) . . ? O7 Dy1 O5 70.27(10) . . ? O6 Dy1 O4 72.62(10) . . ? O2 Dy1 O4 79.04(10) . . ? O7 Dy1 O4 133.62(10) . . ? O5 Dy1 O4 73.86(10) . . ? O6 Dy1 O1 143.82(10) . . ? O2 Dy1 O1 88.79(10) . . ? O7 Dy1 O1 71.42(10) . . ? O5 Dy1 O1 91.79(10) . . ? O4 Dy1 O1 138.46(10) . . ? O6 Dy1 O3 137.71(10) . . ? O2 Dy1 O3 70.94(10) . . ? O7 Dy1 O3 122.25(10) . . ? O5 Dy1 O3 71.66(10) . . ? O4 Dy1 O3 70.36(10) . . ? O1 Dy1 O3 68.12(10) . . ? O6 Dy1 N6 90.92(11) . 4_565 ? O2 Dy1 N6 77.04(11) . 4_565 ? O7 Dy1 N6 71.61(11) . 4_565 ? O5 Dy1 N6 141.86(10) . 4_565 ? O4 Dy1 N6 138.04(10) . 4_565 ? O1 Dy1 N6 74.80(10) . 4_565 ? O3 Dy1 N6 130.67(10) . 4_565 ? C1 O1 Dy1 140.4(3) . . ? C8 O2 Dy1 134.3(3) . . ? C10 O3 Dy1 131.5(3) . . ? C13 O4 Dy1 133.2(3) . . ? C15 O5 Dy1 134.1(3) . . ? C18 O6 Dy1 134.6(3) . . ? C20 O7 Dy1 133.7(3) . . ? C2 N1 N2 113.5(3) . . ? C1 N2 N1 123.6(3) . . ? C1 N2 C6 120.6(3) . . ? N1 N2 C6 115.8(3) . . ? C1 N3 N4 123.5(3) . . ? C1 N3 C7 120.9(3) . . ? N4 N3 C7 115.5(3) . . ? C2 N4 N3 114.1(3) . . ? C3 N5 C4 107.3(3) . . ? C3 N5 H5 126.4 . . ? C4 N5 H5 126.4 . . ? C3 N6 C5 104.5(3) . . ? C3 N6 Dy1 130.3(2) . 4_566 ? C5 N6 Dy1 125.2(2) . 4_566 ? O1 C1 N3 122.0(4) . . ? O1 C1 N2 121.8(4) . . ? N3 C1 N2 116.3(3) . . ? N4 C2 N1 129.1(3) . . ? N4 C2 C3 115.8(3) . . ? N1 C2 C3 115.1(3) . . ? N6 C3 N5 112.0(3) . . ? N6 C3 C2 125.1(3) . . ? N5 C3 C2 122.9(3) . . ? C5 C4 N5 105.7(4) . . ? C5 C4 H4 127.2 . . ? N5 C4 H4 127.2 . . ? C4 C5 N6 110.6(4) . . ? C4 C5 H5A 124.7 . . ? N6 C5 H5A 124.7 . . ? N2 C6 H6A 109.5 . . ? N2 C6 H6B 109.5 . . ? H6A C6 H6B 109.5 . . ? N2 C6 H6C 109.5 . . ? H6A C6 H6C 109.5 . . ? H6B C6 H6C 109.5 . . ? N3 C7 H7A 109.5 . . ? N3 C7 H7B 109.5 . . ? H7A C7 H7B 109.5 . . ? N3 C7 H7C 109.5 . . ? H7A C7 H7C 109.5 . . ? H7B C7 H7C 109.5 . . ? O2 C8 C9 128.2(4) . . ? O2 C8 C11 113.8(5) . . ? C9 C8 C11 117.9(5) . . ? C8 C9 C10 120.0(4) . . ? C8 C9 H9 120.0 . . ? C10 C9 H9 120.0 . . ? O3 C10 C9 127.9(4) . . ? O3 C10 C12 113.9(5) . . ? C9 C10 C12 118.2(5) . . ? F1 C11 F3 107.1(6) . . ? F1 C11 F2 106.4(7) . . ? F3 C11 F2 106.6(6) . . ? F1 C11 C8 111.9(5) . . ? F3 C11 C8 114.3(6) . . ? F2 C11 C8 110.1(5) . . ? F6 C12 F5 108.7(6) . . ? F6 C12 F4 106.1(5) . . ? F5 C12 F4 107.0(6) . . ? F6 C12 C10 114.1(5) . . ? F5 C12 C10 110.2(5) . . ? F4 C12 C10 110.3(5) . . ? O4 C13 C14 128.5(4) . . ? O4 C13 C16 114.2(4) . . ? C14 C13 C16 117.3(4) . . ? C13 C14 C15 122.2(4) . . ? C13 C14 H14 118.9 . . ? C15 C14 H14 118.9 . . ? O5 C15 C14 128.1(4) . . ? O5 C15 C17 115.0(4) . . ? C14 C15 C17 116.9(4) . . ? F7 C16 F9 109.5(5) . . ? F7 C16 F8 104.6(5) . . ? F9 C16 F8 105.0(5) . . ? F7 C16 C13 113.7(4) . . ? F9 C16 C13 113.9(4) . . ? F8 C16 C13 109.4(4) . . ? F11 C17 F12 111.0(6) . . ? F11 C17 F10 105.4(6) . . ? F12 C17 F10 101.9(5) . . ? F11 C17 C15 114.2(4) . . ? F12 C17 C15 111.3(4) . . ? F10 C17 C15 112.3(5) . . ? O6 C18 C19 127.7(4) . . ? O6 C18 C21 113.4(4) . . ? C19 C18 C21 118.9(4) . . ? C18 C19 C20 121.0(4) . . ? C18 C19 H19 119.5 . . ? C20 C19 H19 119.5 . . ? O7 C20 C19 127.4(4) . . ? O7 C20 C22 113.6(4) . . ? C19 C20 C22 119.0(4) . . ? F14 C21 F15 107.4(5) . . ? F14 C21 F13 106.6(5) . . ? F15 C21 F13 107.4(5) . . ? F14 C21 C18 110.1(4) . . ? F15 C21 C18 111.7(4) . . ? F13 C21 C18 113.3(5) . . ? F16 C22 F17 106.6(4) . . ? F16 C22 F18 106.5(5) . . ? F17 C22 F18 107.4(4) . . ? F16 C22 C20 114.5(4) . . ? F17 C22 C20 110.4(4) . . ? F18 C22 C20 111.1(4) . . ? _diffrn_measured_fraction_theta_max 0.971 _diffrn_reflns_theta_full 30.03 _diffrn_measured_fraction_theta_full 0.971 _refine_diff_density_max 1.565 _refine_diff_density_min -0.976 _refine_diff_density_rms 0.132 # Attachment 'CCDC6999838.cif' ######################################################################### data_ln618 _database_code_depnum_ccdc_archive 'CCDC 699838' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C22 H12 F18 N6 O7 Tb' _chemical_formula_sum 'C22 H12 F18 N6 O7 Tb' _chemical_formula_weight 973.30 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Tb Tb -0.1723 4.1537 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M 'P 21/c' _symmetry_space_group_name_Hall '-P 2ybc' _symmetry_Int_Tables_number 14 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 11.345(2) _cell_length_b 18.446(3) _cell_length_c 16.650(3) _cell_angle_alpha 90.00 _cell_angle_beta 107.646(14) _cell_angle_gamma 90.00 _cell_volume 3320.5(10) _cell_formula_units_Z 4 _cell_measurement_temperature 200(2) _cell_measurement_reflns_used 82 _cell_measurement_theta_min 3.8 _cell_measurement_theta_max 19.1 _exptl_crystal_description plate-like _exptl_crystal_colour orange _exptl_crystal_size_max 0.28 _exptl_crystal_size_mid 0.1 _exptl_crystal_size_min 0.04 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.947 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1876 _exptl_absorpt_coefficient_mu 2.281 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.687 _exptl_absorpt_correction_T_max 0.913 _exptl_absorpt_process_details ; R.H. Blessing, Acta Cryst. (1995), A51, 33-38 ; _diffrn_ambient_temperature 200(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 KappaCCD _diffrn_measurement_method 'CCD rotation images, thick slices' _diffrn_detector_area_resol_mean 9 _diffrn_standards_number 0 _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% 0 _diffrn_reflns_number 30495 _diffrn_reflns_av_R_equivalents 0.0847 _diffrn_reflns_av_sigmaI/netI 0.1462 _diffrn_reflns_limit_h_min -15 _diffrn_reflns_limit_h_max 14 _diffrn_reflns_limit_k_min -25 _diffrn_reflns_limit_k_max 25 _diffrn_reflns_limit_l_min -23 _diffrn_reflns_limit_l_max 22 _diffrn_reflns_theta_min 1.69 _diffrn_reflns_theta_max 30.00 _reflns_number_total 9547 _reflns_number_gt 4709 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Collect (Nonius BV, 1997-2000)' _computing_cell_refinement 'Dirax/lsq (Duisenberg & Schreurs, 1989-2000)' _computing_data_reduction 'EvalCCD (Duisenberg & Schreurs 1990-2000)' _computing_structure_solution 'SIR92 (Giacovazzo et al, 1993)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'DIAMOND (Brandenburg, 1999)' _computing_publication_material 'WinGX publication routines (Farrugia, 1999)' _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^)+(0.0430P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 9547 _refine_ls_number_parameters 487 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.1486 _refine_ls_R_factor_gt 0.0470 _refine_ls_wR_factor_ref 0.1110 _refine_ls_wR_factor_gt 0.0825 _refine_ls_goodness_of_fit_ref 0.972 _refine_ls_restrained_S_all 0.972 _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 0.15261(2) 0.270893(14) 0.384003(15) 0.02603(8) Uani 1 1 d . . . O1 O 0.0352(4) 0.28914(19) 0.4814(2) 0.0361(10) Uani 1 1 d . . . O2 O 0.0037(3) 0.1854(2) 0.3118(2) 0.0374(9) Uani 1 1 d . . . O3 O 0.1614(4) 0.1641(2) 0.4749(2) 0.0386(10) Uani 1 1 d . . . O4 O 0.2828(3) 0.1798(2) 0.3528(2) 0.0356(9) Uani 1 1 d . . . O5 O 0.3436(4) 0.2743(2) 0.4952(2) 0.0362(9) Uani 1 1 d . . . O6 O 0.2820(4) 0.3291(2) 0.3178(2) 0.0370(10) Uani 1 1 d . . . O7 O 0.1907(4) 0.3910(2) 0.4399(2) 0.0352(9) Uani 1 1 d . . . N1 N 0.0498(4) 0.2217(3) 0.6845(2) 0.0323(11) Uani 1 1 d . . . N2 N 0.0781(4) 0.2578(2) 0.6199(2) 0.0315(11) Uani 1 1 d . . . N3 N -0.1016(4) 0.2165(3) 0.5212(2) 0.0335(12) Uani 1 1 d . . . N4 N -0.1364(4) 0.1787(3) 0.5818(2) 0.0338(11) Uani 1 1 d . . . N5 N -0.1851(4) 0.0969(3) 0.7102(3) 0.0382(12) Uani 1 1 d . . . H5A H -0.2355 0.0861 0.6617 0.046 Uiso 1 1 calc R . . N6 N -0.0297(4) 0.1492(2) 0.8080(3) 0.0302(11) Uani 1 1 d . . . C1 C 0.0049(5) 0.2553(3) 0.5372(3) 0.0292(13) Uani 1 1 d . . . C2 C -0.0568(5) 0.1844(3) 0.6591(3) 0.0293(12) Uani 1 1 d . . . C3 C -0.0898(5) 0.1449(3) 0.7255(3) 0.0267(12) Uani 1 1 d . . . C4 C -0.1862(6) 0.0688(3) 0.7869(3) 0.0430(16) Uani 1 1 d . . . H4 H -0.2413 0.0348 0.7962 0.052 Uiso 1 1 calc R . . C5 C -0.0906(5) 0.1006(3) 0.8459(3) 0.0362(14) Uani 1 1 d . . . H5 H -0.0688 0.0914 0.9034 0.043 Uiso 1 1 calc R . . C6 C 0.1951(6) 0.2978(4) 0.6445(3) 0.0536(19) Uani 1 1 d . . . H6A H 0.2091 0.3186 0.5954 0.080 Uiso 1 1 calc R . . H6B H 0.2615 0.2653 0.6712 0.080 Uiso 1 1 calc R . . H6C H 0.1913 0.3357 0.6832 0.080 Uiso 1 1 calc R . . C7 C -0.1908(5) 0.2137(4) 0.4356(3) 0.0493(18) Uani 1 1 d . . . H7A H -0.2679 0.2347 0.4364 0.074 Uiso 1 1 calc R . . H7B H -0.2040 0.1642 0.4174 0.074 Uiso 1 1 calc R . . H7C H -0.1585 0.2404 0.3975 0.074 Uiso 1 1 calc R . . C8 C -0.0052(6) 0.1170(4) 0.3154(4) 0.0417(15) Uani 1 1 d . . . C9 C 0.0560(6) 0.0712(3) 0.3802(4) 0.0488(17) Uani 1 1 d . . . H9 H 0.0472 0.0213 0.3730 0.059 Uiso 1 1 calc R . . C10 C 0.1321(6) 0.0995(3) 0.4574(4) 0.0409(15) Uani 1 1 d . . . C11 C -0.0978(9) 0.0833(5) 0.2378(6) 0.079(3) Uani 1 1 d . . . C12 C 0.1880(8) 0.0463(4) 0.5313(5) 0.066(2) Uani 1 1 d . . . C13 C 0.3902(6) 0.1575(3) 0.3909(4) 0.0338(13) Uani 1 1 d . . . C14 C 0.4725(6) 0.1837(3) 0.4646(4) 0.0434(15) Uani 1 1 d . . . H14 H 0.5506 0.1628 0.4838 0.052 Uiso 1 1 calc R . . C15 C 0.4436(6) 0.2400(3) 0.5111(3) 0.0383(14) Uani 1 1 d . . . C16 C 0.4330(7) 0.0924(4) 0.3474(4) 0.0517(18) Uani 1 1 d . . . C17 C 0.5458(6) 0.2658(5) 0.5909(4) 0.0556(18) Uani 1 1 d . . . C18 C 0.3502(5) 0.3849(3) 0.3332(3) 0.0341(13) Uani 1 1 d . . . C19 C 0.3511(6) 0.4405(3) 0.3907(3) 0.0394(15) Uani 1 1 d . . . H19 H 0.4061 0.4790 0.3969 0.047 Uiso 1 1 calc R . . C20 C 0.2695(5) 0.4382(3) 0.4385(3) 0.0318(13) Uani 1 1 d . . . C21 C 0.4466(7) 0.3872(4) 0.2845(4) 0.0549(19) Uani 1 1 d . . . C22 C 0.2726(8) 0.5004(4) 0.5002(4) 0.0529(18) Uani 1 1 d . . . F1 F -0.0869(8) 0.1102(4) 0.1680(3) 0.164(3) Uani 1 1 d . . . F2 F -0.2125(6) 0.0984(3) 0.2363(4) 0.142(3) Uani 1 1 d . . . F3 F -0.0922(5) 0.0125(3) 0.2325(3) 0.1062(19) Uani 1 1 d . . . F4 F 0.1551(5) 0.0650(3) 0.5991(3) 0.0914(16) Uani 1 1 d . . . F5 F 0.3118(5) 0.0493(3) 0.5537(3) 0.0985(16) Uani 1 1 d . . . F6 F 0.1548(5) -0.0223(2) 0.5132(3) 0.111(2) Uani 1 1 d . . . F7 F 0.3890(5) 0.0939(3) 0.2650(3) 0.0998(18) Uani 1 1 d . . . F8 F 0.3881(5) 0.0304(2) 0.3692(3) 0.1023(17) Uani 1 1 d . . . F9 F 0.5531(4) 0.0838(3) 0.3686(3) 0.0956(17) Uani 1 1 d . . . F10 F 0.6036(4) 0.2103(3) 0.6379(3) 0.0897(15) Uani 1 1 d . . . F11 F 0.5054(5) 0.3056(4) 0.6394(3) 0.147(3) Uani 1 1 d . . . F12 F 0.6373(5) 0.2975(3) 0.5703(3) 0.1016(17) Uani 1 1 d . . . F13 F 0.4815(5) 0.4539(3) 0.2724(3) 0.1007(17) Uani 1 1 d . . . F14 F 0.5479(4) 0.3509(3) 0.3255(3) 0.1030(17) Uani 1 1 d . . . F15 F 0.4029(4) 0.3574(3) 0.2082(2) 0.0861(15) Uani 1 1 d . . . F16 F 0.3403(5) 0.5571(2) 0.4923(3) 0.0825(14) Uani 1 1 d . . . F17 F 0.3218(5) 0.4775(2) 0.5798(2) 0.0938(17) Uani 1 1 d . . . F18 F 0.1607(4) 0.5262(2) 0.4943(3) 0.0812(14) 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 Tb1 0.02621(14) 0.02873(14) 0.02585(13) 0.00029(14) 0.01192(9) 0.00023(15) O1 0.040(2) 0.045(3) 0.0304(19) 0.0068(18) 0.0209(17) 0.0010(18) O2 0.034(2) 0.041(2) 0.036(2) 0.001(2) 0.0092(18) -0.002(2) O3 0.045(3) 0.032(2) 0.039(2) 0.0041(19) 0.0122(19) -0.0008(19) O4 0.034(2) 0.036(2) 0.036(2) -0.0004(19) 0.0089(18) 0.0046(19) O5 0.037(2) 0.036(2) 0.035(2) -0.0013(19) 0.0112(17) 0.001(2) O6 0.041(2) 0.042(2) 0.035(2) -0.0062(19) 0.0209(19) -0.004(2) O7 0.039(2) 0.035(2) 0.037(2) 0.0003(18) 0.0192(18) -0.0003(19) N1 0.033(3) 0.045(3) 0.021(2) 0.001(2) 0.0115(19) -0.004(2) N2 0.034(3) 0.042(3) 0.021(2) -0.002(2) 0.0129(19) -0.012(2) N3 0.030(3) 0.051(3) 0.021(2) 0.005(2) 0.0099(19) -0.005(2) N4 0.029(3) 0.053(3) 0.020(2) 0.002(2) 0.008(2) -0.009(2) N5 0.038(3) 0.046(3) 0.029(2) -0.001(2) 0.007(2) -0.015(2) N6 0.040(3) 0.030(2) 0.026(2) 0.004(2) 0.016(2) -0.006(2) C1 0.031(3) 0.035(3) 0.028(3) -0.001(2) 0.017(2) 0.002(2) C2 0.033(3) 0.036(3) 0.024(3) -0.001(2) 0.016(2) -0.002(3) C3 0.026(3) 0.032(3) 0.025(3) -0.003(2) 0.012(2) -0.005(2) C4 0.050(4) 0.048(4) 0.037(3) 0.008(3) 0.021(3) -0.013(3) C5 0.043(4) 0.042(3) 0.027(3) 0.007(3) 0.016(3) -0.005(3) C6 0.053(4) 0.081(5) 0.027(3) -0.003(3) 0.012(3) -0.031(4) C7 0.030(3) 0.088(6) 0.026(3) 0.007(3) 0.002(2) -0.008(3) C8 0.033(4) 0.047(4) 0.047(4) -0.005(3) 0.013(3) -0.007(3) C9 0.048(4) 0.027(3) 0.072(5) 0.005(3) 0.018(4) -0.004(3) C10 0.046(4) 0.040(4) 0.044(3) 0.008(3) 0.023(3) -0.004(3) C11 0.079(7) 0.064(6) 0.085(7) -0.027(5) 0.009(6) -0.018(5) C12 0.071(6) 0.038(4) 0.079(6) 0.015(4) 0.006(5) -0.005(4) C13 0.030(3) 0.030(3) 0.042(3) 0.001(3) 0.012(3) 0.001(3) C14 0.032(4) 0.048(4) 0.048(4) -0.004(3) 0.009(3) 0.007(3) C15 0.032(3) 0.046(4) 0.034(3) 0.000(3) 0.006(3) -0.004(3) C16 0.039(4) 0.057(5) 0.056(4) -0.003(4) 0.010(3) 0.016(4) C17 0.034(4) 0.073(5) 0.051(4) -0.009(4) 0.000(3) 0.005(4) C18 0.029(3) 0.045(4) 0.030(3) 0.008(3) 0.012(3) -0.002(3) C19 0.039(4) 0.043(4) 0.038(3) -0.004(3) 0.015(3) -0.014(3) C20 0.034(4) 0.028(3) 0.031(3) -0.003(3) 0.008(3) -0.002(3) C21 0.055(5) 0.071(5) 0.053(4) -0.002(4) 0.039(4) -0.015(4) C22 0.069(5) 0.050(4) 0.044(4) -0.008(3) 0.022(4) -0.013(4) F1 0.258(9) 0.154(6) 0.054(3) -0.030(4) 0.007(4) -0.100(6) F2 0.076(4) 0.136(5) 0.168(6) -0.068(5) -0.030(4) 0.012(4) F3 0.102(4) 0.064(3) 0.129(4) -0.047(3) 0.000(3) -0.014(3) F4 0.120(4) 0.093(4) 0.063(3) 0.030(3) 0.031(3) -0.009(3) F5 0.087(4) 0.084(3) 0.114(4) 0.043(3) 0.014(3) 0.028(3) F6 0.169(5) 0.037(3) 0.109(4) 0.026(3) 0.013(4) -0.003(3) F7 0.127(4) 0.107(4) 0.058(3) -0.020(3) 0.018(3) 0.069(3) F8 0.134(5) 0.048(3) 0.138(4) -0.023(3) 0.061(4) -0.006(3) F9 0.047(3) 0.096(3) 0.135(4) -0.057(3) 0.015(3) 0.027(3) F10 0.076(3) 0.121(4) 0.052(2) 0.014(3) -0.012(2) 0.003(3) F11 0.065(3) 0.223(7) 0.112(4) -0.123(5) -0.033(3) 0.049(4) F12 0.081(4) 0.126(4) 0.084(3) -0.005(3) 0.004(3) -0.061(3) F13 0.129(4) 0.095(4) 0.113(4) -0.011(3) 0.089(3) -0.053(3) F14 0.049(3) 0.166(5) 0.109(4) 0.026(3) 0.046(3) 0.026(3) F15 0.094(4) 0.130(4) 0.055(2) -0.024(3) 0.054(2) -0.035(3) F16 0.112(4) 0.047(2) 0.097(3) -0.026(2) 0.045(3) -0.032(2) F17 0.165(5) 0.067(3) 0.035(2) -0.014(2) 0.008(3) -0.014(3) F18 0.081(3) 0.080(3) 0.091(3) -0.042(3) 0.037(3) 0.009(3) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag Tb1 O6 2.346(4) . ? Tb1 O2 2.357(4) . ? Tb1 O5 2.386(4) . ? Tb1 O7 2.392(4) . ? Tb1 O4 2.395(4) . ? Tb1 O1 2.414(4) . ? Tb1 O3 2.468(4) . ? Tb1 N6 2.543(4) 4_565 ? O1 C1 1.251(6) . ? O2 C8 1.267(7) . ? O3 C10 1.247(6) . ? O4 C13 1.260(6) . ? O5 C15 1.255(7) . ? O6 C18 1.266(6) . ? O7 C20 1.252(6) . ? N1 C2 1.344(6) . ? N1 N2 1.382(5) . ? N2 C1 1.376(6) . ? N2 C6 1.464(7) . ? N3 C1 1.361(7) . ? N3 N4 1.377(6) . ? N3 C7 1.478(6) . ? N4 C2 1.334(6) . ? N5 C3 1.360(6) . ? N5 C4 1.382(7) . ? N5 H5A 0.8600 . ? N6 C3 1.338(6) . ? N6 C5 1.393(6) . ? N6 Tb1 2.543(4) 4_566 ? C2 C3 1.464(7) . ? C4 C5 1.357(8) . ? C4 H4 0.9300 . ? C5 H5 0.9300 . ? C6 H6A 0.9600 . ? C6 H6B 0.9600 . ? C6 H6C 0.9600 . ? C7 H7A 0.9600 . ? C7 H7B 0.9600 . ? C7 H7C 0.9600 . ? C8 C9 1.381(8) . ? C8 C11 1.529(9) . ? C9 C10 1.412(8) . ? C9 H9 0.9300 . ? C10 C12 1.552(9) . ? C11 F1 1.304(10) . ? C11 F3 1.312(9) . ? C11 F2 1.324(10) . ? C12 F6 1.329(8) . ? C12 F4 1.337(9) . ? C12 F5 1.340(9) . ? C13 C14 1.384(8) . ? C13 C16 1.555(8) . ? C14 C15 1.393(8) . ? C14 H14 0.9300 . ? C15 C17 1.550(8) . ? C16 F9 1.309(7) . ? C16 F7 1.310(7) . ? C16 F8 1.346(8) . ? C17 F11 1.275(8) . ? C17 F12 1.324(8) . ? C17 F10 1.334(8) . ? C18 C19 1.401(8) . ? C18 C21 1.547(8) . ? C19 C20 1.392(8) . ? C19 H19 0.9300 . ? C20 C22 1.535(8) . ? C21 F14 1.327(8) . ? C21 F13 1.327(8) . ? C21 F15 1.334(7) . ? C22 F16 1.326(7) . ? C22 F18 1.332(8) . ? C22 F17 1.341(7) . ? 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 O2 121.38(13) . . ? O6 Tb1 O5 78.57(13) . . ? O2 Tb1 O5 139.06(13) . . ? O6 Tb1 O7 72.17(13) . . ? O2 Tb1 O7 146.67(14) . . ? O5 Tb1 O7 70.06(13) . . ? O6 Tb1 O4 72.79(13) . . ? O2 Tb1 O4 79.29(13) . . ? O5 Tb1 O4 73.27(12) . . ? O7 Tb1 O4 133.11(13) . . ? O6 Tb1 O1 143.43(13) . . ? O2 Tb1 O1 88.83(13) . . ? O5 Tb1 O1 91.80(13) . . ? O7 Tb1 O1 71.38(13) . . ? O4 Tb1 O1 138.20(12) . . ? O6 Tb1 O3 137.64(13) . . ? O2 Tb1 O3 70.59(12) . . ? O5 Tb1 O3 71.78(13) . . ? O7 Tb1 O3 122.15(12) . . ? O4 Tb1 O3 70.15(13) . . ? O1 Tb1 O3 68.11(13) . . ? O6 Tb1 N6 91.79(14) . 4_565 ? O2 Tb1 N6 77.59(14) . 4_565 ? O5 Tb1 N6 141.35(13) . 4_565 ? O7 Tb1 N6 71.36(13) . 4_565 ? O4 Tb1 N6 139.52(12) . 4_565 ? O1 Tb1 N6 73.88(13) . 4_565 ? O3 Tb1 N6 130.05(14) . 4_565 ? C1 O1 Tb1 139.6(3) . . ? C8 O2 Tb1 134.1(4) . . ? C10 O3 Tb1 131.3(4) . . ? C13 O4 Tb1 133.3(3) . . ? C15 O5 Tb1 134.5(3) . . ? C18 O6 Tb1 135.0(3) . . ? C20 O7 Tb1 133.0(4) . . ? C2 N1 N2 113.7(4) . . ? C1 N2 N1 123.4(4) . . ? C1 N2 C6 121.2(4) . . ? N1 N2 C6 115.4(4) . . ? C1 N3 N4 123.9(4) . . ? C1 N3 C7 121.0(4) . . ? N4 N3 C7 115.1(4) . . ? C2 N4 N3 114.0(4) . . ? C3 N5 C4 107.5(4) . . ? C3 N5 H5A 126.2 . . ? C4 N5 H5A 126.2 . . ? C3 N6 C5 105.0(4) . . ? C3 N6 Tb1 129.0(3) . 4_566 ? C5 N6 Tb1 126.0(3) . 4_566 ? O1 C1 N3 123.0(5) . . ? O1 C1 N2 120.6(5) . . ? N3 C1 N2 116.4(4) . . ? N4 C2 N1 128.6(5) . . ? N4 C2 C3 115.9(5) . . ? N1 C2 C3 115.5(4) . . ? N6 C3 N5 111.1(4) . . ? N6 C3 C2 125.3(5) . . ? N5 C3 C2 123.6(4) . . ? C5 C4 N5 106.0(5) . . ? C5 C4 H4 127.0 . . ? N5 C4 H4 127.0 . . ? C4 C5 N6 110.4(5) . . ? C4 C5 H5 124.8 . . ? N6 C5 H5 124.8 . . ? N2 C6 H6A 109.5 . . ? N2 C6 H6B 109.5 . . ? H6A C6 H6B 109.5 . . ? N2 C6 H6C 109.5 . . ? H6A C6 H6C 109.5 . . ? H6B C6 H6C 109.5 . . ? N3 C7 H7A 109.5 . . ? N3 C7 H7B 109.5 . . ? H7A C7 H7B 109.5 . . ? N3 C7 H7C 109.5 . . ? H7A C7 H7C 109.5 . . ? H7B C7 H7C 109.5 . . ? O2 C8 C9 128.1(6) . . ? O2 C8 C11 114.2(6) . . ? C9 C8 C11 117.7(6) . . ? C8 C9 C10 120.6(6) . . ? C8 C9 H9 119.7 . . ? C10 C9 H9 119.7 . . ? O3 C10 C9 127.7(6) . . ? O3 C10 C12 113.7(5) . . ? C9 C10 C12 118.6(6) . . ? F1 C11 F3 107.5(8) . . ? F1 C11 F2 105.1(9) . . ? F3 C11 F2 106.0(8) . . ? F1 C11 C8 111.8(7) . . ? F3 C11 C8 115.3(8) . . ? F2 C11 C8 110.4(7) . . ? F6 C12 F4 107.7(7) . . ? F6 C12 F5 107.7(7) . . ? F4 C12 F5 107.0(7) . . ? F6 C12 C10 113.7(6) . . ? F4 C12 C10 110.8(6) . . ? F5 C12 C10 109.7(6) . . ? O4 C13 C14 128.5(5) . . ? O4 C13 C16 114.1(5) . . ? C14 C13 C16 117.4(5) . . ? C13 C14 C15 122.9(5) . . ? C13 C14 H14 118.5 . . ? C15 C14 H14 118.5 . . ? O5 C15 C14 127.5(5) . . ? O5 C15 C17 114.8(5) . . ? C14 C15 C17 117.7(6) . . ? F9 C16 F7 108.7(6) . . ? F9 C16 F8 105.9(6) . . ? F7 C16 F8 104.2(6) . . ? F9 C16 C13 114.4(6) . . ? F7 C16 C13 113.5(5) . . ? F8 C16 C13 109.4(6) . . ? F11 C17 F12 111.7(8) . . ? F11 C17 F10 106.1(7) . . ? F12 C17 F10 102.0(6) . . ? F11 C17 C15 113.6(6) . . ? F12 C17 C15 110.8(6) . . ? F10 C17 C15 112.0(6) . . ? O6 C18 C19 127.7(5) . . ? O6 C18 C21 113.7(5) . . ? C19 C18 C21 118.5(6) . . ? C20 C19 C18 119.9(5) . . ? C20 C19 H19 120.0 . . ? C18 C19 H19 120.0 . . ? O7 C20 C19 129.4(5) . . ? O7 C20 C22 112.3(5) . . ? C19 C20 C22 118.4(5) . . ? F14 C21 F13 107.1(6) . . ? F14 C21 F15 107.3(6) . . ? F13 C21 F15 106.2(6) . . ? F14 C21 C18 110.9(5) . . ? F13 C21 C18 113.3(6) . . ? F15 C21 C18 111.7(6) . . ? F16 C22 F18 106.2(6) . . ? F16 C22 F17 105.5(6) . . ? F18 C22 F17 106.8(6) . . ? F16 C22 C20 114.8(6) . . ? F18 C22 C20 112.9(6) . . ? F17 C22 C20 110.1(6) . . ? _diffrn_measured_fraction_theta_max 0.986 _diffrn_reflns_theta_full 30.00 _diffrn_measured_fraction_theta_full 0.986 _refine_diff_density_max 2.259 _refine_diff_density_min -1.073 _refine_diff_density_rms 0.163