# Electronic Supplementary Material (ESI) for CrystEngComm # This journal is © The Royal Society of Chemistry 2014 ####################################################################### # # 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_c101130b2 #TrackingRef 'C101130B2-Dy.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C21 H11 Dy F18 N4 O6' _chemical_formula_weight 919.84 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 P21/c loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y-1/2, z-1/2' _cell_length_a 8.8700(18) _cell_length_b 22.049(4) _cell_length_c 15.806(3) _cell_angle_alpha 90.00 _cell_angle_beta 98.02(3) _cell_angle_gamma 90.00 _cell_volume 3061.0(10) _cell_formula_units_Z 4 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 11875 _cell_measurement_theta_min 3.07 _cell_measurement_theta_max 28.03 _exptl_crystal_description block _exptl_crystal_colour colourless _exptl_crystal_size_max 0.20 _exptl_crystal_size_mid 0.20 _exptl_crystal_size_min 0.20 _exptl_crystal_density_meas none _exptl_crystal_density_diffrn 1.996 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1764 _exptl_absorpt_coefficient_mu 2.594 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.6250 _exptl_absorpt_correction_T_max 0.6250 _exptl_absorpt_process_details crystalclear _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 ? _diffrn_measurement_method ? _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 17181 _diffrn_reflns_av_R_equivalents 0.0531 _diffrn_reflns_av_sigmaI/netI 0.0549 _diffrn_reflns_limit_h_min -10 _diffrn_reflns_limit_h_max 10 _diffrn_reflns_limit_k_min -26 _diffrn_reflns_limit_k_max 26 _diffrn_reflns_limit_l_min -18 _diffrn_reflns_limit_l_max 17 _diffrn_reflns_theta_min 3.06 _diffrn_reflns_theta_max 25.01 _reflns_number_total 5115 _reflns_number_gt 3927 _reflns_threshold_expression >2sigma(I) _computing_data_collection ? _computing_cell_refinement ? _computing_data_reduction ? _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _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^)+(0.0496P)^2^+7.4979P] 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 5115 _refine_ls_number_parameters 563 _refine_ls_number_restraints 322 _refine_ls_R_factor_all 0.0872 _refine_ls_R_factor_gt 0.0598 _refine_ls_wR_factor_ref 0.1247 _refine_ls_wR_factor_gt 0.1149 _refine_ls_goodness_of_fit_ref 1.099 _refine_ls_restrained_S_all 1.192 _refine_ls_shift/su_max 0.178 _refine_ls_shift/su_mean 0.008 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 0.90862(5) 0.156206(17) 0.74096(3) 0.05029(17) Uani 1 1 d . A . F1 F 1.2167(17) 0.2990(10) 0.9401(10) 0.111(5) Uani 0.61(2) 1 d PU A 5 F2 F 1.052(2) 0.2607(8) 1.0118(11) 0.112(5) Uani 0.61(2) 1 d PU A 5 F3 F 1.036(2) 0.3517(7) 0.9701(9) 0.105(4) Uani 0.61(2) 1 d PU A 5 F1' F 1.122(4) 0.3544(11) 0.9482(15) 0.108(6) Uani 0.39(2) 1 d PU A 6 F2' F 1.212(2) 0.2651(12) 0.9626(16) 0.102(7) Uani 0.39(2) 1 d PDU A 6 F3' F 1.009(3) 0.2863(15) 1.008(2) 0.112(6) Uani 0.39(2) 1 d PU A 6 F4 F 0.8613(19) 0.3543(7) 0.6030(10) 0.133(4) Uani 0.695(11) 1 d PU A 1 F5 F 0.8130(18) 0.4090(5) 0.7028(8) 0.119(4) Uani 0.695(11) 1 d PU A 1 F6 F 0.6451(13) 0.3495(5) 0.6437(9) 0.106(4) Uani 0.695(11) 1 d PU A 1 F4' F 0.731(4) 0.3372(12) 0.601(2) 0.115(7) Uani 0.305(11) 1 d PU A 2 F5' F 0.902(3) 0.3923(14) 0.657(2) 0.118(7) Uani 0.305(11) 1 d PU A 2 F6' F 0.696(3) 0.3893(14) 0.7107(18) 0.127(7) Uani 0.305(11) 1 d PDU A 2 F7 F 0.8150(10) -0.0639(3) 0.7694(6) 0.144(3) Uani 1 1 d U . . F8 F 0.5860(11) -0.0619(4) 0.7715(7) 0.173(4) Uani 1 1 d U . . F9 F 0.6687(13) -0.0432(4) 0.6630(7) 0.161(4) Uani 1 1 d U . . F10 F 0.5082(10) 0.0963(4) 0.9645(5) 0.145(3) Uani 1 1 d U . . F11 F 0.5766(12) 0.1824(5) 0.9468(6) 0.154(3) Uani 1 1 d U . . F12 F 0.3892(12) 0.1476(5) 0.8696(6) 0.160(4) Uani 1 1 d U . . F13 F 1.220(3) -0.0044(7) 0.6534(14) 0.102(5) Uani 0.506(19) 1 d PU B 7 F14 F 1.186(3) 0.0336(9) 0.5361(12) 0.107(5) Uani 0.506(19) 1 d PU B 7 F15 F 1.4005(17) 0.0434(7) 0.6114(14) 0.099(5) Uani 0.506(19) 1 d PU B 7 F13' F 1.304(2) 0.0054(8) 0.6758(10) 0.098(5) Uani 0.494(19) 1 d PDU B 8 F14' F 1.133(2) 0.0150(9) 0.5647(15) 0.109(5) Uani 0.494(19) 1 d PU B 8 F15' F 1.350(2) 0.0492(8) 0.5600(14) 0.108(5) Uani 0.494(19) 1 d PDU B 8 F16 F 1.3641(16) 0.2827(6) 0.7654(9) 0.114(4) Uani 0.643(11) 1 d PU B 3 F17 F 1.2619(15) 0.3036(5) 0.6408(9) 0.106(4) Uani 0.643(11) 1 d PU B 3 F18 F 1.4641(17) 0.2502(7) 0.6609(13) 0.131(5) Uani 0.643(11) 1 d PU B 3 F16' F 1.481(3) 0.2445(11) 0.7281(18) 0.119(6) Uani 0.357(11) 1 d PU B 4 F17' F 1.295(3) 0.3012(12) 0.710(2) 0.111(6) Uani 0.357(11) 1 d PU B 4 F18' F 1.389(3) 0.2664(10) 0.6072(14) 0.104(6) Uani 0.357(11) 1 d PU B 4 C1 C 0.7366(13) 0.1020(4) 0.5481(7) 0.076(3) Uani 1 1 d . . . H1 H 0.7733 0.0634 0.5625 0.092 Uiso 1 1 calc R . . C2 C 0.6541(15) 0.1157(6) 0.4750(8) 0.102(4) Uani 1 1 d . . . H2 H 0.6253 0.0898 0.4292 0.122 Uiso 1 1 calc R . . C3 C 0.6200(15) 0.1747(6) 0.4800(8) 0.106(4) Uani 1 1 d . . . H3 H 0.5591 0.1974 0.4391 0.127 Uiso 1 1 calc R . . C4 C 1.0942(12) 0.0416(4) 0.8633(7) 0.075(3) Uani 1 1 d . . . H4 H 1.0877 0.0161 0.8162 0.090 Uiso 1 1 calc R . . C5 C 1.1578(14) 0.0252(6) 0.9429(9) 0.096(4) Uani 1 1 d . . . H5 H 1.2019 -0.0118 0.9604 0.115 Uiso 1 1 calc R . . C6 C 1.1428(15) 0.0738(7) 0.9900(8) 0.102(4) Uani 1 1 d . . . H6 H 1.1749 0.0772 1.0484 0.122 Uiso 1 1 calc R . . C7 C 1.0819(16) 0.2966(6) 0.9474(9) 0.095(4) Uani 1 1 d D . . C8 C 0.9874(10) 0.2768(5) 0.8647(6) 0.062(3) Uani 1 1 d . A . C9 C 0.9297(12) 0.3191(4) 0.8071(7) 0.070(3) Uani 1 1 d . . . H9 H 0.9472 0.3598 0.8201 0.084 Uiso 1 1 calc R A . C10 C 0.8482(10) 0.3045(4) 0.7318(7) 0.060(2) Uani 1 1 d . A . C11 C 0.7879(18) 0.3550(5) 0.6698(10) 0.095(4) Uani 1 1 d D . . C12 C 0.6967(15) -0.0346(5) 0.7414(10) 0.098(4) Uani 1 1 d . . . C13 C 0.7079(11) 0.0315(4) 0.7648(7) 0.065(3) Uani 1 1 d . A . C14 C 0.6207(12) 0.0538(5) 0.8211(7) 0.079(3) Uani 1 1 d . . . H14 H 0.5567 0.0279 0.8459 0.095 Uiso 1 1 calc R . . C15 C 0.6256(11) 0.1146(5) 0.8420(6) 0.066(3) Uani 1 1 d . A . C16 C 0.5255(16) 0.1375(8) 0.9047(9) 0.106(5) Uani 1 1 d . . . C17 C 1.2477(14) 0.0429(5) 0.6127(8) 0.081(3) Uani 1 1 d D . . C18 C 1.1936(11) 0.1002(4) 0.6499(6) 0.056(2) Uani 1 1 d . A . C19 C 1.2865(11) 0.1497(4) 0.6550(6) 0.063(2) Uani 1 1 d . . . H19 H 1.3820 0.1474 0.6372 0.076 Uiso 1 1 calc R B . C20 C 1.2368(10) 0.2036(4) 0.6870(6) 0.054(2) Uani 1 1 d . A . C21 C 1.3357(14) 0.2595(6) 0.6864(12) 0.104(5) Uani 1 1 d . . . N1 N 0.7608(9) 0.1493(3) 0.5981(5) 0.062(2) Uani 1 1 d . . . N2 N 0.6890(10) 0.1940(4) 0.5536(6) 0.086(3) Uani 1 1 d . . . H2A H 0.6878 0.2309 0.5709 0.103 Uiso 1 1 calc R . . N3 N 1.0434(9) 0.0969(4) 0.8599(5) 0.066(2) Uani 1 1 d . . . N4 N 1.0743(11) 0.1169(4) 0.9402(6) 0.084(3) Uani 1 1 d . . . H4A H 1.0529 0.1526 0.9571 0.101 Uiso 1 1 calc R . . O1 O 0.9746(7) 0.2210(3) 0.8578(4) 0.0609(16) Uani 1 1 d . . . O2 O 0.8170(6) 0.2531(2) 0.7019(4) 0.0543(15) Uani 1 1 d . . . O3 O 0.7990(7) 0.0586(3) 0.7284(4) 0.0677(17) Uani 1 1 d . . . O4 O 0.7030(7) 0.1540(3) 0.8147(4) 0.0670(17) Uani 1 1 d . . . O5 O 1.0668(7) 0.0959(3) 0.6729(4) 0.0626(16) Uani 1 1 d . . . O6 O 1.1164(6) 0.2127(3) 0.7151(4) 0.0581(15) 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 0.0525(3) 0.0369(2) 0.0625(3) -0.0077(2) 0.0115(2) -0.00597(19) F1 0.098(7) 0.131(9) 0.101(7) -0.020(7) -0.002(6) -0.015(7) F2 0.146(9) 0.109(9) 0.076(6) -0.004(7) 0.003(7) 0.005(7) F3 0.116(8) 0.100(7) 0.096(7) -0.050(6) 0.002(6) 0.001(6) F1' 0.119(10) 0.097(9) 0.102(9) -0.025(7) -0.005(8) -0.029(8) F2' 0.096(9) 0.104(11) 0.099(10) -0.014(8) -0.011(8) 0.004(8) F3' 0.119(10) 0.122(10) 0.094(9) -0.014(9) 0.014(8) 0.010(8) F4 0.150(8) 0.130(8) 0.127(7) 0.041(6) 0.043(7) 0.017(7) F5 0.145(8) 0.067(6) 0.138(7) 0.003(5) -0.005(7) -0.009(5) F6 0.087(6) 0.100(6) 0.123(7) 0.030(6) -0.015(6) 0.003(5) F4' 0.121(10) 0.104(10) 0.114(10) 0.013(8) -0.005(9) 0.002(9) F5' 0.125(10) 0.104(10) 0.122(10) 0.027(8) 0.010(8) -0.011(8) F6' 0.123(10) 0.115(10) 0.141(10) 0.007(8) 0.009(9) 0.031(9) F7 0.123(5) 0.073(5) 0.220(8) -0.010(5) -0.031(6) 0.017(4) F8 0.178(7) 0.090(5) 0.261(9) -0.019(6) 0.070(7) -0.054(5) F9 0.222(8) 0.087(5) 0.159(7) -0.042(5) -0.022(6) -0.020(5) F10 0.164(7) 0.160(7) 0.123(6) 0.008(5) 0.066(5) -0.022(6) F11 0.181(7) 0.152(7) 0.144(6) -0.045(6) 0.081(6) -0.039(6) F12 0.121(6) 0.232(9) 0.135(6) -0.005(6) 0.041(6) 0.037(6) F13 0.118(9) 0.071(7) 0.121(8) 0.003(6) 0.028(7) 0.019(7) F14 0.135(9) 0.093(8) 0.094(8) -0.031(7) 0.021(7) 0.012(7) F15 0.094(7) 0.094(7) 0.110(9) -0.016(7) 0.017(7) 0.038(6) F13' 0.104(9) 0.075(7) 0.109(8) 0.002(6) -0.011(7) 0.033(7) F14' 0.113(9) 0.095(8) 0.121(9) -0.048(7) 0.022(7) 0.002(7) F15' 0.120(9) 0.108(8) 0.105(9) -0.017(7) 0.046(8) 0.017(7) F16 0.121(7) 0.104(7) 0.109(7) -0.022(6) -0.009(6) -0.050(6) F17 0.120(7) 0.071(6) 0.123(7) 0.024(6) 0.003(6) -0.026(5) F18 0.107(7) 0.133(8) 0.159(9) -0.006(8) 0.037(8) -0.028(6) F16' 0.103(9) 0.126(9) 0.122(10) 0.007(8) 0.001(8) -0.027(8) F17' 0.108(9) 0.094(9) 0.131(10) -0.004(9) 0.019(9) -0.020(8) F18' 0.110(9) 0.102(9) 0.103(9) 0.017(8) 0.020(8) -0.035(7) C1 0.098(8) 0.049(6) 0.077(7) -0.025(5) -0.006(7) 0.010(5) C2 0.124(11) 0.086(10) 0.085(9) -0.040(7) -0.025(8) 0.012(8) C3 0.104(10) 0.113(11) 0.083(9) -0.016(8) -0.046(8) 0.029(8) C4 0.086(7) 0.049(6) 0.085(8) 0.000(5) -0.007(7) 0.000(5) C5 0.107(10) 0.072(8) 0.107(10) 0.022(8) 0.003(8) 0.006(7) C6 0.118(11) 0.107(11) 0.078(8) 0.030(8) 0.008(8) 0.002(9) C7 0.115(11) 0.083(10) 0.089(10) -0.029(8) 0.021(10) -0.021(8) C8 0.060(6) 0.067(7) 0.061(6) -0.028(5) 0.013(5) -0.007(5) C9 0.082(7) 0.038(5) 0.087(8) -0.021(5) 0.003(7) -0.009(5) C10 0.058(6) 0.044(5) 0.079(7) -0.009(5) 0.016(6) -0.010(4) C11 0.123(12) 0.039(7) 0.116(11) -0.015(6) -0.012(10) -0.013(6) C12 0.093(9) 0.055(7) 0.138(12) 0.007(8) -0.007(9) -0.030(7) C13 0.045(5) 0.054(6) 0.092(8) 0.011(6) -0.011(6) -0.012(5) C14 0.078(7) 0.064(7) 0.098(8) 0.010(6) 0.019(7) -0.027(6) C15 0.056(6) 0.078(8) 0.063(6) 0.004(5) 0.010(5) -0.007(5) C16 0.078(9) 0.148(14) 0.093(10) -0.021(9) 0.022(9) -0.056(9) C17 0.093(9) 0.060(7) 0.093(9) -0.004(6) 0.027(8) 0.006(6) C18 0.070(6) 0.045(5) 0.052(5) 0.000(4) 0.007(5) 0.018(5) C19 0.057(6) 0.062(6) 0.072(6) -0.001(5) 0.015(5) 0.009(5) C20 0.055(6) 0.050(5) 0.054(5) 0.002(4) 0.001(5) -0.003(4) C21 0.059(7) 0.082(9) 0.185(17) -0.051(10) 0.064(10) -0.016(6) N1 0.069(5) 0.046(5) 0.068(5) -0.011(4) -0.001(4) 0.004(4) N2 0.087(7) 0.069(6) 0.096(7) -0.019(5) -0.004(6) 0.011(5) N3 0.068(5) 0.054(5) 0.074(6) -0.002(4) 0.010(5) -0.003(4) N4 0.105(7) 0.079(7) 0.069(6) 0.000(5) 0.012(6) 0.008(5) O1 0.076(4) 0.049(4) 0.057(4) -0.012(3) 0.008(3) -0.008(3) O2 0.049(3) 0.042(3) 0.070(4) -0.010(3) 0.004(3) -0.005(3) O3 0.067(4) 0.049(4) 0.089(5) -0.010(3) 0.015(4) -0.012(3) O4 0.058(4) 0.058(4) 0.090(5) -0.002(4) 0.026(4) -0.008(3) O5 0.071(4) 0.043(3) 0.076(4) -0.009(3) 0.017(4) -0.002(3) O6 0.048(3) 0.051(4) 0.079(4) -0.010(3) 0.022(3) -0.005(3) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag Dy1 O4 2.298(6) . ? Dy1 O5 2.305(6) . ? Dy1 O6 2.308(6) . ? Dy1 O2 2.337(6) . ? Dy1 O1 2.344(6) . ? Dy1 O3 2.358(6) . ? Dy1 N1 2.453(8) . ? Dy1 N3 2.459(8) . ? F1 C7 1.219(19) . ? F2 C7 1.34(2) . ? F3 C7 1.348(17) . ? F1' C7 1.32(2) . ? F2' C7 1.340(11) . ? F3' C7 1.24(3) . ? F4 C11 1.317(18) . ? F5 C11 1.304(15) . ? F6 C11 1.282(17) . ? F4' C11 1.20(3) . ? F5' C11 1.34(3) . ? F6' C11 1.343(11) . ? F7 C12 1.259(14) . ? F8 C12 1.297(14) . ? F9 C12 1.244(15) . ? F10 C16 1.335(16) . ? F11 C16 1.243(14) . ? F12 C16 1.278(15) . ? F13 C17 1.269(19) . ? F14 C17 1.27(2) . ? F15 C17 1.358(19) . ? F13' C17 1.337(10) . ? F14' C17 1.33(2) . ? F15' C17 1.322(10) . ? F16 C21 1.341(19) . ? F17 C21 1.327(19) . ? F18 C21 1.277(16) . ? F16' C21 1.40(3) . ? F17' C21 1.07(3) . ? F18' C21 1.41(2) . ? C1 N1 1.307(11) . ? C1 C2 1.313(15) . ? C1 H1 0.9300 . ? C2 C3 1.340(16) . ? C2 H2 0.9300 . ? C3 N2 1.308(13) . ? C3 H3 0.9300 . ? C4 N3 1.298(11) . ? C4 C5 1.354(15) . ? C4 H4 0.9300 . ? C5 C6 1.322(17) . ? C5 H5 0.9300 . ? C6 N4 1.327(14) . ? C6 H6 0.9300 . ? C7 C8 1.515(15) . ? C8 O1 1.239(11) . ? C8 C9 1.353(13) . ? C9 C10 1.342(13) . ? C9 H9 0.9300 . ? C10 O2 1.244(10) . ? C10 C11 1.531(16) . ? C12 C13 1.503(15) . ? C13 O3 1.213(11) . ? C13 C14 1.349(14) . ? C14 C15 1.380(14) . ? C14 H14 0.9300 . ? C15 O4 1.224(11) . ? C15 C16 1.507(17) . ? C17 C18 1.500(13) . ? C18 O5 1.233(10) . ? C18 C19 1.363(13) . ? C19 C20 1.387(12) . ? C19 H19 0.9300 . ? C20 O6 1.229(10) . ? C20 C21 1.514(14) . ? N1 N2 1.320(11) . ? N2 H2A 0.8600 . ? N3 N4 1.334(11) . ? N4 H4A 0.8600 . ? 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 O4 Dy1 O5 143.4(2) . . ? O4 Dy1 O6 144.2(2) . . ? O5 Dy1 O6 71.1(2) . . ? O4 Dy1 O2 83.2(2) . . ? O5 Dy1 O2 128.0(2) . . ? O6 Dy1 O2 73.5(2) . . ? O4 Dy1 O1 75.0(2) . . ? O5 Dy1 O1 128.2(2) . . ? O6 Dy1 O1 72.1(2) . . ? O2 Dy1 O1 72.0(2) . . ? O4 Dy1 O3 71.1(2) . . ? O5 Dy1 O3 72.9(2) . . ? O6 Dy1 O3 143.9(2) . . ? O2 Dy1 O3 133.4(2) . . ? O1 Dy1 O3 132.6(2) . . ? O4 Dy1 N1 96.1(3) . . ? O5 Dy1 N1 79.4(2) . . ? O6 Dy1 N1 102.0(2) . . ? O2 Dy1 N1 72.1(2) . . ? O1 Dy1 N1 143.7(2) . . ? O3 Dy1 N1 72.8(2) . . ? O4 Dy1 N3 86.4(2) . . ? O5 Dy1 N3 77.7(3) . . ? O6 Dy1 N3 96.2(2) . . ? O2 Dy1 N3 143.3(2) . . ? O1 Dy1 N3 71.3(2) . . ? O3 Dy1 N3 74.3(2) . . ? N1 Dy1 N3 144.2(3) . . ? N1 C1 C2 111.9(10) . . ? N1 C1 H1 124.0 . . ? C2 C1 H1 124.0 . . ? C1 C2 C3 105.8(10) . . ? C1 C2 H2 127.1 . . ? C3 C2 H2 127.1 . . ? N2 C3 C2 106.7(11) . . ? N2 C3 H3 126.6 . . ? C2 C3 H3 126.7 . . ? N3 C4 C5 112.8(11) . . ? N3 C4 H4 123.6 . . ? C5 C4 H4 123.6 . . ? C6 C5 C4 104.1(11) . . ? C6 C5 H5 127.9 . . ? C4 C5 H5 127.9 . . ? C5 C6 N4 108.7(12) . . ? C5 C6 H6 125.6 . . ? N4 C6 H6 125.6 . . ? F1 C7 F3' 134(2) . . ? F1 C7 F1' 71.9(15) . . ? F3' C7 F1' 109.7(19) . . ? F1 C7 F2' 37.6(11) . . ? F3' C7 F2' 107(2) . . ? F1' C7 F2' 105.7(18) . . ? F1 C7 F2 113.3(17) . . ? F3' C7 F2 30.2(14) . . ? F1' C7 F2 129.9(16) . . ? F2' C7 F2 79.2(16) . . ? F1 C7 F3 109.0(14) . . ? F3' C7 F3 75.5(16) . . ? F1' C7 F3 38.9(11) . . ? F2' C7 F3 135.0(16) . . ? F2 C7 F3 103.3(14) . . ? F1 C7 C8 111.3(12) . . ? F3' C7 C8 109.0(16) . . ? F1' C7 C8 113.7(15) . . ? F2' C7 C8 111.4(13) . . ? F2 C7 C8 110.0(12) . . ? F3 C7 C8 109.6(12) . . ? O1 C8 C9 127.1(9) . . ? O1 C8 C7 113.2(10) . . ? C9 C8 C7 119.6(10) . . ? C10 C9 C8 122.5(9) . . ? C10 C9 H9 118.7 . . ? C8 C9 H9 118.7 . . ? O2 C10 C9 128.3(9) . . ? O2 C10 C11 112.4(9) . . ? C9 C10 C11 119.3(9) . . ? F4' C11 F6 53.2(18) . . ? F4' C11 F5 133.4(18) . . ? F6 C11 F5 108.7(14) . . ? F4' C11 F4 57.6(19) . . ? F6 C11 F4 108.5(14) . . ? F5 C11 F4 104.8(14) . . ? F4' C11 F6' 114(3) . . ? F6 C11 F6' 64.4(17) . . ? F5 C11 F6' 51.4(15) . . ? F4 C11 F6' 142.7(18) . . ? F4' C11 F5' 107(3) . . ? F6 C11 F5' 137.9(17) . . ? F5 C11 F5' 54.1(15) . . ? F4 C11 F5' 54.3(16) . . ? F6' C11 F5' 105(2) . . ? F4' C11 C10 114.0(15) . . ? F6 C11 C10 112.2(11) . . ? F5 C11 C10 112.6(12) . . ? F4 C11 C10 109.7(11) . . ? F6' C11 C10 106.5(16) . . ? F5' C11 C10 109.8(16) . . ? F9 C12 F7 108.2(15) . . ? F9 C12 F8 103.7(12) . . ? F7 C12 F8 105.6(12) . . ? F9 C12 C13 113.0(11) . . ? F7 C12 C13 112.8(10) . . ? F8 C12 C13 112.8(12) . . ? O3 C13 C14 127.9(10) . . ? O3 C13 C12 112.7(11) . . ? C14 C13 C12 119.4(10) . . ? C13 C14 C15 120.6(9) . . ? C13 C14 H14 119.7 . . ? C15 C14 H14 119.7 . . ? O4 C15 C14 127.3(10) . . ? O4 C15 C16 113.8(10) . . ? C14 C15 C16 118.8(10) . . ? F11 C16 F12 110.2(16) . . ? F11 C16 F10 103.5(12) . . ? F12 C16 F10 103.3(10) . . ? F11 C16 C15 114.6(10) . . ? F12 C16 C15 112.4(12) . . ? F10 C16 C15 111.9(14) . . ? F13 C17 F14 105.2(15) . . ? F13 C17 F15' 127.2(14) . . ? F14 C17 F15' 70.0(13) . . ? F13 C17 F14' 73.8(13) . . ? F14 C17 F14' 36.2(10) . . ? F15' C17 F14' 103.1(14) . . ? F13 C17 F13' 36.0(9) . . ? F14 C17 F13' 132.4(15) . . ? F15' C17 F13' 108.6(14) . . ? F14' C17 F13' 108.3(14) . . ? F13 C17 F15 106.2(13) . . ? F14 C17 F15 106.4(14) . . ? F15' C17 F15 38.3(9) . . ? F14' C17 F15 132.8(14) . . ? F13' C17 F15 75.4(12) . . ? F13 C17 C18 113.4(11) . . ? F14 C17 C18 113.1(12) . . ? F15' C17 C18 116.4(11) . . ? F14' C17 C18 110.6(12) . . ? F13' C17 C18 109.5(11) . . ? F15 C17 C18 112.0(12) . . ? O5 C18 C19 127.8(8) . . ? O5 C18 C17 114.0(9) . . ? C19 C18 C17 118.2(9) . . ? C18 C19 C20 119.1(9) . . ? C18 C19 H19 120.4 . . ? C20 C19 H19 120.4 . . ? O6 C20 C19 127.5(8) . . ? O6 C20 C21 113.7(8) . . ? C19 C20 C21 118.8(9) . . ? F17' C21 F18 127.2(18) . . ? F17' C21 F17 53.0(19) . . ? F18 C21 F17 109.9(17) . . ? F17' C21 F16 51.5(18) . . ? F18 C21 F16 107.2(15) . . ? F17 C21 F16 104.0(13) . . ? F17' C21 F16' 112(2) . . ? F18 C21 F16' 46.3(12) . . ? F17 C21 F16' 141.2(15) . . ? F16 C21 F16' 67.1(15) . . ? F17' C21 F18' 113(2) . . ? F18 C21 F18' 46.4(11) . . ? F17 C21 F18' 68.9(16) . . ? F16 C21 F18' 138.1(13) . . ? F16' C21 F18' 92.4(16) . . ? F17' C21 C20 118.2(16) . . ? F18 C21 C20 114.5(12) . . ? F17 C21 C20 110.9(11) . . ? F16 C21 C20 109.8(13) . . ? F16' C21 C20 107.4(15) . . ? F18' C21 C20 111.2(13) . . ? C1 N1 N2 104.3(9) . . ? C1 N1 Dy1 128.9(7) . . ? N2 N1 Dy1 126.8(6) . . ? C3 N2 N1 111.2(10) . . ? C3 N2 H2A 124.4 . . ? N1 N2 H2A 124.4 . . ? C4 N3 N4 104.3(9) . . ? C4 N3 Dy1 131.3(7) . . ? N4 N3 Dy1 124.4(6) . . ? C6 N4 N3 110.1(10) . . ? C6 N4 H4A 125.0 . . ? N3 N4 H4A 125.0 . . ? C8 O1 Dy1 133.2(6) . . ? C10 O2 Dy1 133.0(6) . . ? C13 O3 Dy1 134.8(7) . . ? C15 O4 Dy1 135.9(7) . . ? C18 O5 Dy1 137.1(6) . . ? C20 O6 Dy1 137.0(6) . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag N1 C1 C2 C3 -2.0(16) . . . . ? C1 C2 C3 N2 2.9(16) . . . . ? N3 C4 C5 C6 0.4(15) . . . . ? C4 C5 C6 N4 -0.3(15) . . . . ? F1 C7 C8 O1 88.0(17) . . . . ? F3' C7 C8 O1 -70(2) . . . . ? F1' C7 C8 O1 166.9(19) . . . . ? F2' C7 C8 O1 48(2) . . . . ? F2 C7 C8 O1 -38.3(17) . . . . ? F3 C7 C8 O1 -151.3(13) . . . . ? F1 C7 C8 C9 -90.7(18) . . . . ? F3' C7 C8 C9 111(2) . . . . ? F1' C7 C8 C9 -12(2) . . . . ? F2' C7 C8 C9 -131.2(19) . . . . ? F2 C7 C8 C9 142.9(15) . . . . ? F3 C7 C8 C9 29.9(18) . . . . ? O1 C8 C9 C10 -0.2(17) . . . . ? C7 C8 C9 C10 178.4(10) . . . . ? C8 C9 C10 O2 -2.5(17) . . . . ? C8 C9 C10 C11 -179.6(11) . . . . ? O2 C10 C11 F4' -5(3) . . . . ? C9 C10 C11 F4' 173(2) . . . . ? O2 C10 C11 F6 53.4(16) . . . . ? C9 C10 C11 F6 -129.1(13) . . . . ? O2 C10 C11 F5 176.4(13) . . . . ? C9 C10 C11 F5 -6(2) . . . . ? O2 C10 C11 F4 -67.3(15) . . . . ? C9 C10 C11 F4 110.3(14) . . . . ? O2 C10 C11 F6' 122(2) . . . . ? C9 C10 C11 F6' -60(2) . . . . ? O2 C10 C11 F5' -125(2) . . . . ? C9 C10 C11 F5' 52(2) . . . . ? F9 C12 C13 O3 -54.4(15) . . . . ? F7 C12 C13 O3 68.7(15) . . . . ? F8 C12 C13 O3 -171.7(11) . . . . ? F9 C12 C13 C14 125.6(13) . . . . ? F7 C12 C13 C14 -111.2(13) . . . . ? F8 C12 C13 C14 8.3(17) . . . . ? O3 C13 C14 C15 1.7(17) . . . . ? C12 C13 C14 C15 -178.3(11) . . . . ? C13 C14 C15 O4 0.2(18) . . . . ? C13 C14 C15 C16 179.6(11) . . . . ? O4 C15 C16 F11 -29.2(19) . . . . ? C14 C15 C16 F11 151.3(14) . . . . ? O4 C15 C16 F12 97.7(13) . . . . ? C14 C15 C16 F12 -81.8(16) . . . . ? O4 C15 C16 F10 -146.6(10) . . . . ? C14 C15 C16 F10 34.0(16) . . . . ? F13 C17 C18 O5 -41.8(18) . . . . ? F14 C17 C18 O5 77.9(17) . . . . ? F15' C17 C18 O5 156.1(16) . . . . ? F14' C17 C18 O5 38.9(17) . . . . ? F13' C17 C18 O5 -80.3(16) . . . . ? F15 C17 C18 O5 -162.0(13) . . . . ? F13 C17 C18 C19 137.9(16) . . . . ? F14 C17 C18 C19 -102.4(18) . . . . ? F15' C17 C18 C19 -24(2) . . . . ? F14' C17 C18 C19 -141.4(16) . . . . ? F13' C17 C18 C19 99.4(15) . . . . ? F15 C17 C18 C19 17.7(17) . . . . ? O5 C18 C19 C20 -2.1(16) . . . . ? C17 C18 C19 C20 178.2(9) . . . . ? C18 C19 C20 O6 2.4(16) . . . . ? C18 C19 C20 C21 -175.6(11) . . . . ? O6 C20 C21 F17' 0(3) . . . . ? C19 C20 C21 F17' 179(3) . . . . ? O6 C20 C21 F18 177.1(16) . . . . ? C19 C20 C21 F18 -5(2) . . . . ? O6 C20 C21 F17 -57.8(17) . . . . ? C19 C20 C21 F17 120.4(12) . . . . ? O6 C20 C21 F16 56.5(17) . . . . ? C19 C20 C21 F16 -125.2(13) . . . . ? O6 C20 C21 F16' 127.8(16) . . . . ? C19 C20 C21 F16' -54(2) . . . . ? O6 C20 C21 F18' -132.5(15) . . . . ? C19 C20 C21 F18' 46(2) . . . . ? C2 C1 N1 N2 0.4(13) . . . . ? C2 C1 N1 Dy1 -178.6(8) . . . . ? O4 Dy1 N1 C1 -101.0(9) . . . . ? O5 Dy1 N1 C1 42.2(9) . . . . ? O6 Dy1 N1 C1 110.0(9) . . . . ? O2 Dy1 N1 C1 178.1(9) . . . . ? O1 Dy1 N1 C1 -173.9(8) . . . . ? O3 Dy1 N1 C1 -33.0(9) . . . . ? N3 Dy1 N1 C1 -8.8(11) . . . . ? O4 Dy1 N1 N2 80.2(8) . . . . ? O5 Dy1 N1 N2 -136.6(8) . . . . ? O6 Dy1 N1 N2 -68.7(8) . . . . ? O2 Dy1 N1 N2 -0.7(7) . . . . ? O1 Dy1 N1 N2 7.3(10) . . . . ? O3 Dy1 N1 N2 148.2(8) . . . . ? N3 Dy1 N1 N2 172.4(7) . . . . ? C2 C3 N2 N1 -2.8(15) . . . . ? C1 N1 N2 C3 1.5(13) . . . . ? Dy1 N1 N2 C3 -179.4(8) . . . . ? C5 C4 N3 N4 -0.3(12) . . . . ? C5 C4 N3 Dy1 -177.7(7) . . . . ? O4 Dy1 N3 C4 113.3(9) . . . . ? O5 Dy1 N3 C4 -33.5(9) . . . . ? O6 Dy1 N3 C4 -102.5(9) . . . . ? O2 Dy1 N3 C4 -173.2(8) . . . . ? O1 Dy1 N3 C4 -171.3(9) . . . . ? O3 Dy1 N3 C4 41.9(9) . . . . ? N1 Dy1 N3 C4 18.0(11) . . . . ? O4 Dy1 N3 N4 -63.5(7) . . . . ? O5 Dy1 N3 N4 149.7(8) . . . . ? O6 Dy1 N3 N4 80.6(8) . . . . ? O2 Dy1 N3 N4 10.0(9) . . . . ? O1 Dy1 N3 N4 11.9(7) . . . . ? O3 Dy1 N3 N4 -134.9(8) . . . . ? N1 Dy1 N3 N4 -158.9(7) . . . . ? C5 C6 N4 N3 0.1(15) . . . . ? C4 N3 N4 C6 0.1(12) . . . . ? Dy1 N3 N4 C6 177.7(8) . . . . ? C9 C8 O1 Dy1 17.9(15) . . . . ? C7 C8 O1 Dy1 -160.8(7) . . . . ? O4 Dy1 O1 C8 -108.4(8) . . . . ? O5 Dy1 O1 C8 103.8(8) . . . . ? O6 Dy1 O1 C8 57.2(8) . . . . ? O2 Dy1 O1 C8 -20.8(8) . . . . ? O3 Dy1 O1 C8 -153.9(7) . . . . ? N1 Dy1 O1 C8 -28.7(10) . . . . ? N3 Dy1 O1 C8 160.4(8) . . . . ? C9 C10 O2 Dy1 -12.6(15) . . . . ? C11 C10 O2 Dy1 164.6(8) . . . . ? O4 Dy1 O2 C10 94.5(8) . . . . ? O5 Dy1 O2 C10 -106.7(8) . . . . ? O6 Dy1 O2 C10 -58.0(8) . . . . ? O1 Dy1 O2 C10 18.1(7) . . . . ? O3 Dy1 O2 C10 150.4(7) . . . . ? N1 Dy1 O2 C10 -166.8(8) . . . . ? N3 Dy1 O2 C10 20.0(9) . . . . ? C14 C13 O3 Dy1 9.8(16) . . . . ? C12 C13 O3 Dy1 -170.2(8) . . . . ? O4 Dy1 O3 C13 -14.1(8) . . . . ? O5 Dy1 O3 C13 159.1(9) . . . . ? O6 Dy1 O3 C13 156.1(8) . . . . ? O2 Dy1 O3 C13 -74.4(9) . . . . ? O1 Dy1 O3 C13 32.6(10) . . . . ? N1 Dy1 O3 C13 -117.0(9) . . . . ? N3 Dy1 O3 C13 77.4(9) . . . . ? C14 C15 O4 Dy1 -14.4(17) . . . . ? C16 C15 O4 Dy1 166.2(8) . . . . ? O5 Dy1 O4 C15 5.5(11) . . . . ? O6 Dy1 O4 C15 -153.8(8) . . . . ? O2 Dy1 O4 C15 157.0(9) . . . . ? O1 Dy1 O4 C15 -129.9(10) . . . . ? O3 Dy1 O4 C15 16.4(9) . . . . ? N1 Dy1 O4 C15 85.9(9) . . . . ? N3 Dy1 O4 C15 -58.3(9) . . . . ? C19 C18 O5 Dy1 -4.1(16) . . . . ? C17 C18 O5 Dy1 175.6(7) . . . . ? O4 Dy1 O5 C18 -161.2(8) . . . . ? O6 Dy1 O5 C18 6.2(9) . . . . ? O2 Dy1 O5 C18 55.8(9) . . . . ? O1 Dy1 O5 C18 -40.8(10) . . . . ? O3 Dy1 O5 C18 -172.0(9) . . . . ? N1 Dy1 O5 C18 112.9(9) . . . . ? N3 Dy1 O5 C18 -94.8(9) . . . . ? C19 C20 O6 Dy1 3.4(15) . . . . ? C21 C20 O6 Dy1 -178.5(9) . . . . ? O4 Dy1 O6 C20 161.3(8) . . . . ? O5 Dy1 O6 C20 -5.8(8) . . . . ? O2 Dy1 O6 C20 -147.1(9) . . . . ? O1 Dy1 O6 C20 137.0(9) . . . . ? O3 Dy1 O6 C20 -2.9(11) . . . . ? N1 Dy1 O6 C20 -80.1(9) . . . . ? N3 Dy1 O6 C20 68.9(9) . . . . ? _diffrn_measured_fraction_theta_max 0.946 _diffrn_reflns_theta_full 25.01 _diffrn_measured_fraction_theta_full 0.946 _refine_diff_density_max 0.758 _refine_diff_density_min -0.501 _refine_diff_density_rms 0.102 _database_code_depnum_ccdc_archive 'CCDC 803916' ####################################################################### # # 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_shelxs #TrackingRef 'C110101M-g101107b_Tb.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C21 H11 F18 N4 O6 Tb' _chemical_formula_weight 916.27 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' 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' Tb Tb -0.1723 4.1537 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Monoclinic _symmetry_space_group_name_H-M P21/c loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y-1/2, z-1/2' _cell_length_a 8.9400(18) _cell_length_b 22.222(4) _cell_length_c 15.950(3) _cell_angle_alpha 90.00 _cell_angle_beta 97.63(3) _cell_angle_gamma 90.00 _cell_volume 3140.6(10) _cell_formula_units_Z 4 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 20002 _cell_measurement_theta_min 3.035 _cell_measurement_theta_max 27.67 _exptl_crystal_description ? _exptl_crystal_colour ? _exptl_crystal_size_max 0.20 _exptl_crystal_size_mid 0.20 _exptl_crystal_size_min 0.16 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.938 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1760 _exptl_absorpt_coefficient_mu 2.401 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.6453 _exptl_absorpt_correction_T_max 0.7000 _exptl_absorpt_process_details crystalclear _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 'Bruker P4' _diffrn_measurement_method '\w scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 19188 _diffrn_reflns_av_R_equivalents 0.0479 _diffrn_reflns_av_sigmaI/netI 0.0445 _diffrn_reflns_limit_h_min -10 _diffrn_reflns_limit_h_max 8 _diffrn_reflns_limit_k_min -26 _diffrn_reflns_limit_k_max 26 _diffrn_reflns_limit_l_min -18 _diffrn_reflns_limit_l_max 18 _diffrn_reflns_theta_min 3.04 _diffrn_reflns_theta_max 25.01 _reflns_number_total 5530 _reflns_number_gt 4595 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker XSCANS' _computing_cell_refinement 'Bruker XSCANS' _computing_data_reduction 'Bruker SHELXTL' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0719P)^2^+6.0594P] 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 5530 _refine_ls_number_parameters 535 _refine_ls_number_restraints 275 _refine_ls_R_factor_all 0.0695 _refine_ls_R_factor_gt 0.0551 _refine_ls_wR_factor_ref 0.1428 _refine_ls_wR_factor_gt 0.1338 _refine_ls_goodness_of_fit_ref 1.102 _refine_ls_restrained_S_all 1.219 _refine_ls_shift/su_max 0.138 _refine_ls_shift/su_mean 0.006 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 0.90854(4) 0.156453(15) 0.24045(2) 0.04829(17) Uani 1 1 d . A . F1 F 1.2170(10) 0.2868(5) 0.4476(6) 0.162(4) Uani 1 1 d U . . F2 F 1.0400(11) 0.2703(5) 0.5108(5) 0.147(3) Uani 1 1 d U . . F3 F 1.0597(12) 0.3541(4) 0.4647(6) 0.157(4) Uani 1 1 d U . . F4 F 0.8654(18) 0.3565(7) 0.1037(9) 0.136(4) Uani 0.711(11) 1 d PU A 3 F5 F 0.8087(16) 0.4096(4) 0.2032(8) 0.119(4) Uani 0.711(11) 1 d PU A 3 F6 F 0.6494(13) 0.3492(5) 0.1397(8) 0.110(4) Uani 0.711(11) 1 d PU A 3 F4' F 0.749(4) 0.3374(12) 0.095(2) 0.114(7) Uani 0.289(11) 1 d PU A 4 F5' F 0.898(3) 0.3958(13) 0.162(2) 0.120(7) Uani 0.289(11) 1 d PDU A 4 F6' F 0.676(3) 0.3810(15) 0.205(2) 0.134(7) Uani 0.289(11) 1 d PDU A 4 F7 F 0.5766(12) 0.1812(5) 0.4475(6) 0.153(3) Uani 1 1 d U . . F8 F 0.3867(11) 0.1463(5) 0.3695(6) 0.164(4) Uani 1 1 d U . . F9 F 0.5082(10) 0.0948(4) 0.4658(5) 0.141(3) Uani 1 1 d U . . F10 F 0.8142(9) -0.0640(3) 0.2698(6) 0.138(3) Uani 1 1 d U . . F11 F 0.6662(12) -0.0429(4) 0.1625(6) 0.151(3) Uani 1 1 d U . . F12 F 0.5847(11) -0.0626(4) 0.2693(7) 0.174(4) Uani 1 1 d U . . F13 F 1.180(2) 0.0324(7) 0.0382(9) 0.099(4) Uani 0.544(19) 1 d PU B 5 F14 F 1.230(2) -0.0041(7) 0.1571(12) 0.106(4) Uani 0.544(19) 1 d PU B 5 F15 F 1.3989(16) 0.0432(7) 0.1079(13) 0.106(4) Uani 0.544(19) 1 d PU B 5 F13' F 1.1339(19) 0.0135(10) 0.0685(16) 0.113(5) Uani 0.456(19) 1 d PDU B 6 F14' F 1.312(3) 0.0070(9) 0.1745(13) 0.102(5) Uani 0.456(19) 1 d PU B 6 F15' F 1.348(2) 0.0488(8) 0.0573(14) 0.110(5) Uani 0.456(19) 1 d PDU B 6 F16 F 1.2647(14) 0.3044(5) 0.1458(8) 0.106(4) Uani 0.629(11) 1 d PU B 1 F17 F 1.4609(17) 0.2506(7) 0.1521(13) 0.131(4) Uani 0.629(11) 1 d PU B 1 F18 F 1.3747(18) 0.2792(7) 0.2669(10) 0.126(4) Uani 0.629(11) 1 d PU B 1 F16' F 1.373(3) 0.2702(11) 0.1078(11) 0.120(6) Uani 0.371(11) 1 d PDU B 2 F17' F 1.484(2) 0.2439(10) 0.2203(16) 0.110(6) Uani 0.371(11) 1 d PU B 2 F18' F 1.309(3) 0.2998(11) 0.230(2) 0.119(6) Uani 0.371(11) 1 d PU B 2 C1 C 0.7354(12) 0.1019(4) 0.0479(6) 0.078(3) Uani 1 1 d . . . H1 H 0.7708 0.0635 0.0626 0.094 Uiso 1 1 calc R . . C2 C 0.6511(15) 0.1162(6) -0.0259(7) 0.108(4) Uani 1 1 d . . . H2A H 0.6193 0.0904 -0.0706 0.130 Uiso 1 1 calc R . . C3 C 0.6222(15) 0.1759(6) -0.0215(8) 0.109(5) Uani 1 1 d . . . H3 H 0.5656 0.1991 -0.0627 0.131 Uiso 1 1 calc R . . C4 C 1.0753(10) 0.1171(4) 0.4397(5) 0.059(2) Uani 1 1 d . . . H4A H 1.0539 0.1558 0.4569 0.071 Uiso 1 1 calc R . . C5 C 1.1402(15) 0.0763(6) 0.4904(8) 0.103(4) Uani 1 1 d . . . H5 H 1.1710 0.0812 0.5480 0.124 Uiso 1 1 calc R . . C6 C 1.1553(14) 0.0263(6) 0.4462(8) 0.096(4) Uani 1 1 d . . . H6 H 1.1986 -0.0101 0.4652 0.115 Uiso 1 1 calc R . . C7 C 1.0789(15) 0.2981(5) 0.4453(7) 0.085(3) Uani 1 1 d . . . C8 C 0.9881(10) 0.2773(4) 0.3647(5) 0.061(2) Uani 1 1 d . . . C9 C 0.9305(11) 0.3199(4) 0.3065(6) 0.068(2) Uani 1 1 d . . . H9 H 0.9468 0.3604 0.3197 0.081 Uiso 1 1 calc R . . C10 C 0.8502(10) 0.3053(3) 0.2300(6) 0.057(2) Uani 1 1 d . A . C11 C 0.7898(14) 0.3553(4) 0.1701(8) 0.085(3) Uani 1 1 d D . . C12 C 0.5219(14) 0.1366(6) 0.4052(8) 0.093(4) Uani 1 1 d . . . C13 C 0.6240(10) 0.1143(5) 0.3434(6) 0.066(2) Uani 1 1 d . A . C14 C 0.6197(12) 0.0542(4) 0.3214(7) 0.079(3) Uani 1 1 d . . . H14 H 0.5556 0.0285 0.3458 0.095 Uiso 1 1 calc R . . C15 C 0.7073(10) 0.0312(4) 0.2644(6) 0.066(2) Uani 1 1 d . A . C16 C 0.6971(13) -0.0346(5) 0.2401(9) 0.089(3) Uani 1 1 d . . . C17 C 1.2499(12) 0.0430(4) 0.1125(7) 0.080(3) Uani 1 1 d D . . C18 C 1.1947(10) 0.1004(4) 0.1495(5) 0.056(2) Uani 1 1 d . A . C19 C 1.2882(10) 0.1502(4) 0.1553(6) 0.062(2) Uani 1 1 d . . . H19 H 1.3834 0.1478 0.1381 0.075 Uiso 1 1 calc R B . C20 C 1.2393(9) 0.2035(4) 0.1869(5) 0.056(2) Uani 1 1 d . A . C21 C 1.3374(14) 0.2604(6) 0.1862(10) 0.102(4) Uani 1 1 d D . . N1 N 0.7612(9) 0.1503(3) 0.0967(5) 0.0638(19) Uani 1 1 d . . . N2 N 0.6895(10) 0.1950(4) 0.0522(6) 0.085(3) Uani 1 1 d . . . H2 H 0.6874 0.2316 0.0695 0.102 Uiso 1 1 calc R . . N3 N 1.0428(8) 0.0976(3) 0.3608(5) 0.0639(18) Uani 1 1 d . . . N4 N 1.0913(11) 0.0415(4) 0.3650(7) 0.105(3) Uani 1 1 d . . . H4 H 1.0840 0.0173 0.3226 0.126 Uiso 1 1 calc R . . O1 O 0.9750(7) 0.2218(3) 0.3580(3) 0.0615(14) Uani 1 1 d . . . O2 O 0.8177(6) 0.2538(2) 0.2016(3) 0.0533(13) Uani 1 1 d . . . O3 O 0.7024(7) 0.1539(2) 0.3153(4) 0.0647(16) Uani 1 1 d . . . O4 O 0.7975(7) 0.0590(3) 0.2280(4) 0.0686(16) Uani 1 1 d . . . O5 O 1.0683(7) 0.0959(2) 0.1725(4) 0.0644(15) Uani 1 1 d . . . O6 O 1.1194(6) 0.2130(2) 0.2147(4) 0.0591(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 0.0503(3) 0.0341(2) 0.0612(3) -0.00768(15) 0.01007(17) -0.00633(15) F1 0.111(6) 0.227(8) 0.137(6) -0.074(6) -0.023(5) -0.005(6) F2 0.183(7) 0.169(7) 0.082(4) -0.008(5) -0.003(4) -0.038(6) F3 0.210(8) 0.113(6) 0.134(6) -0.068(5) -0.033(5) 0.004(5) F4 0.151(8) 0.136(8) 0.128(7) 0.053(6) 0.044(7) 0.011(7) F5 0.151(8) 0.056(5) 0.142(7) -0.001(5) -0.009(6) -0.002(5) F6 0.099(6) 0.097(6) 0.124(7) 0.032(5) -0.017(5) -0.002(5) F4' 0.120(10) 0.101(10) 0.114(10) 0.018(8) -0.009(9) 0.010(9) F5' 0.126(10) 0.105(10) 0.128(10) 0.020(8) 0.008(8) -0.013(9) F6' 0.132(10) 0.120(10) 0.148(10) 0.015(9) 0.010(9) 0.020(9) F7 0.175(7) 0.152(7) 0.148(6) -0.037(6) 0.073(6) -0.036(6) F8 0.118(6) 0.239(9) 0.144(6) -0.007(6) 0.046(5) 0.045(6) F9 0.162(7) 0.154(7) 0.116(5) 0.015(5) 0.053(5) -0.024(5) F10 0.121(5) 0.072(4) 0.208(7) -0.007(4) -0.032(5) 0.016(4) F11 0.205(8) 0.086(5) 0.153(6) -0.040(5) -0.017(6) -0.021(5) F12 0.173(8) 0.097(6) 0.260(9) -0.020(6) 0.063(7) -0.058(5) F13 0.136(8) 0.081(7) 0.082(7) -0.028(6) 0.019(6) 0.018(6) F14 0.123(9) 0.071(7) 0.130(8) 0.005(6) 0.035(7) 0.022(7) F15 0.098(7) 0.099(7) 0.123(8) -0.021(7) 0.027(6) 0.036(6) F13' 0.119(9) 0.098(9) 0.124(9) -0.042(7) 0.026(7) 0.000(7) F14' 0.107(9) 0.074(8) 0.120(8) -0.005(6) -0.002(7) 0.032(7) F15' 0.122(9) 0.104(8) 0.112(9) -0.022(7) 0.048(7) 0.026(7) F16 0.117(7) 0.060(5) 0.140(7) 0.019(5) 0.014(6) -0.020(5) F17 0.105(7) 0.130(8) 0.168(9) -0.011(7) 0.047(7) -0.027(6) F18 0.127(8) 0.113(8) 0.129(8) -0.018(6) -0.016(6) -0.047(6) F16' 0.127(10) 0.109(9) 0.127(9) 0.024(8) 0.023(8) -0.034(8) F17' 0.087(8) 0.115(9) 0.125(9) 0.008(8) -0.002(8) -0.029(7) F18' 0.120(10) 0.097(9) 0.140(10) -0.012(8) 0.022(8) -0.018(8) C1 0.100(8) 0.048(5) 0.083(7) -0.024(5) -0.004(6) 0.009(5) C2 0.134(11) 0.102(10) 0.079(7) -0.040(7) -0.024(7) 0.006(8) C3 0.120(10) 0.098(9) 0.095(8) -0.022(7) -0.044(7) 0.030(8) C4 0.074(6) 0.054(5) 0.050(5) 0.007(4) 0.008(4) 0.007(4) C5 0.122(11) 0.105(10) 0.083(8) 0.011(7) 0.014(7) -0.006(8) C6 0.096(8) 0.086(8) 0.102(9) 0.033(7) -0.003(7) -0.001(7) C7 0.105(9) 0.068(7) 0.078(7) -0.017(5) -0.001(6) 0.000(6) C8 0.066(5) 0.059(5) 0.059(5) -0.023(4) 0.015(4) -0.007(4) C9 0.078(6) 0.038(4) 0.084(6) -0.016(4) 0.002(5) -0.008(4) C10 0.053(5) 0.038(4) 0.083(6) -0.008(4) 0.016(4) -0.001(4) C11 0.091(8) 0.046(5) 0.113(9) -0.012(5) -0.003(7) -0.005(5) C12 0.074(8) 0.110(9) 0.099(9) -0.012(7) 0.023(6) -0.042(7) C13 0.052(5) 0.076(6) 0.068(5) 0.008(5) 0.005(4) -0.011(5) C14 0.082(7) 0.059(6) 0.099(7) 0.003(5) 0.023(6) -0.024(5) C15 0.061(5) 0.043(5) 0.087(6) 0.008(4) -0.021(5) -0.018(4) C16 0.081(7) 0.050(6) 0.125(10) 0.008(6) -0.022(6) -0.021(5) C17 0.094(8) 0.057(6) 0.094(8) -0.004(5) 0.029(6) 0.020(6) C18 0.064(5) 0.050(5) 0.054(5) -0.001(4) 0.009(4) 0.018(4) C19 0.052(5) 0.060(6) 0.077(6) -0.001(4) 0.015(4) 0.005(4) C20 0.050(5) 0.060(5) 0.060(5) -0.003(4) 0.009(4) -0.004(4) C21 0.065(7) 0.089(9) 0.161(13) -0.039(9) 0.055(8) -0.023(6) N1 0.072(5) 0.047(4) 0.070(5) -0.013(3) -0.001(4) -0.001(3) N2 0.089(6) 0.061(5) 0.100(6) -0.023(5) -0.009(5) 0.019(4) N3 0.067(5) 0.046(4) 0.078(5) -0.002(3) 0.009(4) -0.002(3) N4 0.109(8) 0.075(7) 0.123(8) 0.002(6) -0.013(6) -0.005(6) O1 0.077(4) 0.053(3) 0.055(3) -0.011(3) 0.012(3) -0.008(3) O2 0.050(3) 0.037(3) 0.071(3) -0.007(2) 0.002(2) -0.005(2) O3 0.054(3) 0.054(4) 0.091(4) 0.000(3) 0.027(3) -0.006(3) O4 0.068(4) 0.044(3) 0.095(4) -0.006(3) 0.016(3) -0.014(3) O5 0.070(4) 0.041(3) 0.084(4) -0.012(3) 0.017(3) 0.001(3) O6 0.052(3) 0.048(3) 0.078(4) -0.015(3) 0.016(3) -0.008(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 O3 2.326(6) . ? Tb1 O5 2.332(6) . ? Tb1 O6 2.347(5) . ? Tb1 O2 2.364(5) . ? Tb1 O4 2.379(6) . ? Tb1 O1 2.384(5) . ? Tb1 N1 2.492(7) . ? Tb1 N3 2.495(8) . ? F1 C7 1.255(13) . ? F2 C7 1.301(13) . ? F3 C7 1.301(12) . ? F4 C11 1.330(17) . ? F5 C11 1.318(13) . ? F6 C11 1.292(15) . ? F4' C11 1.27(3) . ? F5' C11 1.338(11) . ? F6' C11 1.345(11) . ? F7 C12 1.260(13) . ? F8 C12 1.284(15) . ? F9 C12 1.359(15) . ? F10 C16 1.270(12) . ? F11 C16 1.245(14) . ? F12 C16 1.319(13) . ? F13 C17 1.285(18) . ? F14 C17 1.291(18) . ? F15 C17 1.344(17) . ? F13' C17 1.344(10) . ? F14' C17 1.33(2) . ? F15' C17 1.328(10) . ? F16 C21 1.296(18) . ? F17 C21 1.312(17) . ? F18 C21 1.353(19) . ? F16' C21 1.348(11) . ? F17' C21 1.40(2) . ? F18' C21 1.16(3) . ? C1 N1 1.329(11) . ? C1 C2 1.348(15) . ? C1 H1 0.9300 . ? C2 C3 1.355(17) . ? C2 H2A 0.9300 . ? C3 N2 1.317(13) . ? C3 H3 0.9300 . ? C4 C5 1.299(14) . ? C4 N3 1.326(11) . ? C4 H4A 0.9300 . ? C5 C6 1.333(17) . ? C5 H5 0.9300 . ? C6 N4 1.386(14) . ? C6 H6 0.9300 . ? C7 C8 1.499(13) . ? C8 O1 1.241(10) . ? C8 C9 1.377(13) . ? C9 C10 1.370(12) . ? C9 H9 0.9300 . ? C10 O2 1.251(9) . ? C10 C11 1.517(14) . ? C12 C13 1.514(15) . ? C13 O3 1.244(10) . ? C13 C14 1.382(13) . ? C14 C15 1.374(14) . ? C14 H14 0.9300 . ? C15 O4 1.223(11) . ? C15 C16 1.512(13) . ? C17 C18 1.516(12) . ? C18 O5 1.238(10) . ? C18 C19 1.382(12) . ? C19 C20 1.379(12) . ? C19 H19 0.9300 . ? C20 O6 1.232(9) . ? C20 C21 1.541(14) . ? N1 N2 1.334(11) . ? N2 H2 0.8600 . ? N3 N4 1.319(11) . ? N4 H4 0.8600 . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag O3 Tb1 O5 143.2(2) . . ? O3 Tb1 O6 144.35(19) . . ? O5 Tb1 O6 70.9(2) . . ? O3 Tb1 O2 83.60(19) . . ? O5 Tb1 O2 128.1(2) . . ? O6 Tb1 O2 73.77(19) . . ? O3 Tb1 O4 70.7(2) . . ? O5 Tb1 O4 73.2(2) . . ? O6 Tb1 O4 144.0(2) . . ? O2 Tb1 O4 133.3(2) . . ? O3 Tb1 O1 75.1(2) . . ? O5 Tb1 O1 127.8(2) . . ? O6 Tb1 O1 71.89(19) . . ? O2 Tb1 O1 71.91(19) . . ? O4 Tb1 O1 132.7(2) . . ? O3 Tb1 N1 96.5(3) . . ? O5 Tb1 N1 79.8(2) . . ? O6 Tb1 N1 102.0(2) . . ? O2 Tb1 N1 71.8(2) . . ? O4 Tb1 N1 73.1(2) . . ? O1 Tb1 N1 143.4(2) . . ? O3 Tb1 N3 85.7(2) . . ? O5 Tb1 N3 78.1(2) . . ? O6 Tb1 N3 95.7(2) . . ? O2 Tb1 N3 142.6(2) . . ? O4 Tb1 N3 74.9(2) . . ? O1 Tb1 N3 70.7(2) . . ? N1 Tb1 N3 145.2(2) . . ? N1 C1 C2 110.7(9) . . ? N1 C1 H1 124.7 . . ? C2 C1 H1 124.6 . . ? C1 C2 C3 105.9(9) . . ? C1 C2 H2A 127.0 . . ? C3 C2 H2A 127.0 . . ? N2 C3 C2 107.0(10) . . ? N2 C3 H3 126.5 . . ? C2 C3 H3 126.5 . . ? C5 C4 N3 112.8(10) . . ? C5 C4 H4A 123.6 . . ? N3 C4 H4A 123.6 . . ? C4 C5 C6 108.7(11) . . ? C4 C5 H5 125.7 . . ? C6 C5 H5 125.7 . . ? C5 C6 N4 103.5(11) . . ? C5 C6 H6 128.3 . . ? N4 C6 H6 128.3 . . ? F1 C7 F3 110.2(11) . . ? F1 C7 F2 104.4(11) . . ? F3 C7 F2 101.9(11) . . ? F1 C7 C8 112.5(9) . . ? F3 C7 C8 115.2(10) . . ? F2 C7 C8 111.7(10) . . ? O1 C8 C9 127.1(8) . . ? O1 C8 C7 114.5(9) . . ? C9 C8 C7 118.5(8) . . ? C10 C9 C8 122.8(8) . . ? C10 C9 H9 118.6 . . ? C8 C9 H9 118.6 . . ? O2 C10 C9 127.5(8) . . ? O2 C10 C11 113.4(8) . . ? C9 C10 C11 119.2(8) . . ? F4' C11 F6 57.8(17) . . ? F4' C11 F5 132.1(16) . . ? F6 C11 F5 108.3(12) . . ? F4' C11 F4 50.8(17) . . ? F6 C11 F4 105.9(13) . . ? F5 C11 F4 104.4(12) . . ? F4' C11 F5' 104(2) . . ? F6 C11 F5' 135.4(16) . . ? F5 C11 F5' 50.8(15) . . ? F4 C11 F5' 57.4(16) . . ? F4' C11 F6' 112(2) . . ? F6 C11 F6' 56.7(16) . . ? F5 C11 F6' 60.7(16) . . ? F4 C11 F6' 144.0(17) . . ? F5' C11 F6' 110(2) . . ? F4' C11 C10 113.4(14) . . ? F6 C11 C10 113.9(9) . . ? F5 C11 C10 113.7(10) . . ? F4 C11 C10 109.9(10) . . ? F5' C11 C10 110.6(15) . . ? F6' C11 C10 106.1(16) . . ? F7 C12 F8 112.5(14) . . ? F7 C12 F9 102.8(11) . . ? F8 C12 F9 105.2(10) . . ? F7 C12 C13 112.5(9) . . ? F8 C12 C13 112.3(10) . . ? F9 C12 C13 111.0(12) . . ? O3 C13 C14 126.2(9) . . ? O3 C13 C12 114.8(9) . . ? C14 C13 C12 118.9(9) . . ? C15 C14 C13 121.9(9) . . ? C15 C14 H14 119.1 . . ? C13 C14 H14 119.1 . . ? O4 C15 C14 126.6(8) . . ? O4 C15 C16 112.9(10) . . ? C14 C15 C16 120.6(9) . . ? F11 C16 F10 110.9(13) . . ? F11 C16 F12 101.6(10) . . ? F10 C16 F12 104.8(11) . . ? F11 C16 C15 113.4(10) . . ? F10 C16 C15 112.5(9) . . ? F12 C16 C15 112.8(11) . . ? F13 C17 F14 106.0(14) . . ? F13 C17 F15' 71.8(12) . . ? F14 C17 F15' 126.4(13) . . ? F13 C17 F14' 132.5(14) . . ? F14 C17 F14' 34.6(10) . . ? F15' C17 F14' 107.8(15) . . ? F13 C17 F15 108.2(12) . . ? F14 C17 F15 103.9(13) . . ? F15' C17 F15 38.5(9) . . ? F14' C17 F15 74.2(12) . . ? F13 C17 F13' 35.3(10) . . ? F14 C17 F13' 74.9(13) . . ? F15' C17 F13' 103.5(14) . . ? F14' C17 F13' 107.9(15) . . ? F15 C17 F13' 132.5(13) . . ? F13 C17 C18 111.8(10) . . ? F14 C17 C18 113.1(10) . . ? F15' C17 C18 117.0(11) . . ? F14' C17 C18 109.9(11) . . ? F15 C17 C18 113.3(10) . . ? F13' C17 C18 110.3(11) . . ? O5 C18 C19 127.8(8) . . ? O5 C18 C17 113.8(8) . . ? C19 C18 C17 118.4(8) . . ? C20 C19 C18 119.6(8) . . ? C20 C19 H19 120.2 . . ? C18 C19 H19 120.2 . . ? O6 C20 C19 127.7(8) . . ? O6 C20 C21 112.6(8) . . ? C19 C20 C21 119.6(8) . . ? F18' C21 F16 66.2(17) . . ? F18' C21 F17 129.1(17) . . ? F16 C21 F17 108.3(15) . . ? F18' C21 F16' 122(2) . . ? F16 C21 F16' 65.4(15) . . ? F17 C21 F16' 47.6(11) . . ? F18' C21 F18 41.1(14) . . ? F16 C21 F18 106.6(13) . . ? F17 C21 F18 109.3(14) . . ? F16' C21 F18 140.7(15) . . ? F18' C21 F17' 103(2) . . ? F16 C21 F17' 140.6(13) . . ? F17 C21 F17' 47.2(11) . . ? F16' C21 F17' 94.3(16) . . ? F18 C21 F17' 67.1(13) . . ? F18' C21 C20 116.5(15) . . ? F16 C21 C20 112.0(11) . . ? F17 C21 C20 112.2(11) . . ? F16' C21 C20 110.2(13) . . ? F18 C21 C20 108.3(11) . . ? F17' C21 C20 106.6(13) . . ? C1 N1 N2 104.9(8) . . ? C1 N1 Tb1 127.8(6) . . ? N2 N1 Tb1 127.3(5) . . ? C3 N2 N1 111.4(9) . . ? C3 N2 H2 124.3 . . ? N1 N2 H2 124.3 . . ? N4 N3 C4 103.4(8) . . ? N4 N3 Tb1 130.9(7) . . ? C4 N3 Tb1 125.6(6) . . ? N3 N4 C6 111.7(10) . . ? N3 N4 H4 124.2 . . ? C6 N4 H4 124.2 . . ? C8 O1 Tb1 133.1(6) . . ? C10 O2 Tb1 133.4(5) . . ? C13 O3 Tb1 136.4(6) . . ? C15 O4 Tb1 135.7(6) . . ? C18 O5 Tb1 136.9(5) . . ? C20 O6 Tb1 136.8(5) . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag N1 C1 C2 C3 -0.9(16) . . . . ? C1 C2 C3 N2 0.6(16) . . . . ? N3 C4 C5 C6 0.4(15) . . . . ? C4 C5 C6 N4 -0.7(15) . . . . ? F1 C7 C8 O1 71.1(14) . . . . ? F3 C7 C8 O1 -161.5(11) . . . . ? F2 C7 C8 O1 -46.0(13) . . . . ? F1 C7 C8 C9 -108.2(12) . . . . ? F3 C7 C8 C9 19.2(16) . . . . ? F2 C7 C8 C9 134.8(11) . . . . ? O1 C8 C9 C10 -1.2(16) . . . . ? C7 C8 C9 C10 177.9(9) . . . . ? C8 C9 C10 O2 -0.1(15) . . . . ? C8 C9 C10 C11 179.5(9) . . . . ? O2 C10 C11 F4' -16(2) . . . . ? C9 C10 C11 F4' 165(2) . . . . ? O2 C10 C11 F6 48.0(14) . . . . ? C9 C10 C11 F6 -131.6(12) . . . . ? O2 C10 C11 F5 172.7(11) . . . . ? C9 C10 C11 F5 -6.9(17) . . . . ? O2 C10 C11 F4 -70.6(14) . . . . ? C9 C10 C11 F4 109.8(13) . . . . ? O2 C10 C11 F5' -132(2) . . . . ? C9 C10 C11 F5' 48(2) . . . . ? O2 C10 C11 F6' 108(2) . . . . ? C9 C10 C11 F6' -71(2) . . . . ? F7 C12 C13 O3 -30.9(16) . . . . ? F8 C12 C13 O3 97.2(12) . . . . ? F9 C12 C13 O3 -145.4(9) . . . . ? F7 C12 C13 C14 151.0(12) . . . . ? F8 C12 C13 C14 -80.9(14) . . . . ? F9 C12 C13 C14 36.5(14) . . . . ? O3 C13 C14 C15 0.9(16) . . . . ? C12 C13 C14 C15 178.8(10) . . . . ? C13 C14 C15 O4 0.8(16) . . . . ? C13 C14 C15 C16 -178.5(9) . . . . ? O4 C15 C16 F11 -55.6(13) . . . . ? C14 C15 C16 F11 123.8(12) . . . . ? O4 C15 C16 F10 71.2(13) . . . . ? C14 C15 C16 F10 -109.4(13) . . . . ? O4 C15 C16 F12 -170.5(10) . . . . ? C14 C15 C16 F12 8.9(15) . . . . ? F13 C17 C18 O5 73.5(15) . . . . ? F14 C17 C18 O5 -46.1(17) . . . . ? F15' C17 C18 O5 153.5(15) . . . . ? F14' C17 C18 O5 -83.2(16) . . . . ? F15 C17 C18 O5 -163.9(12) . . . . ? F13' C17 C18 O5 35.7(18) . . . . ? F13 C17 C18 C19 -107.5(15) . . . . ? F14 C17 C18 C19 132.8(15) . . . . ? F15' C17 C18 C19 -27.6(19) . . . . ? F14' C17 C18 C19 95.7(15) . . . . ? F15 C17 C18 C19 15.0(16) . . . . ? F13' C17 C18 C19 -145.4(16) . . . . ? O5 C18 C19 C20 -2.9(15) . . . . ? C17 C18 C19 C20 178.4(8) . . . . ? C18 C19 C20 O6 2.8(15) . . . . ? C18 C19 C20 C21 -174.7(10) . . . . ? O6 C20 C21 F18' 19(3) . . . . ? C19 C20 C21 F18' -163(2) . . . . ? O6 C20 C21 F16 -54.5(14) . . . . ? C19 C20 C21 F16 123.3(12) . . . . ? O6 C20 C21 F17 -176.5(14) . . . . ? C19 C20 C21 F17 1(2) . . . . ? O6 C20 C21 F16' -125.3(17) . . . . ? C19 C20 C21 F16' 53(2) . . . . ? O6 C20 C21 F18 62.7(15) . . . . ? C19 C20 C21 F18 -119.5(13) . . . . ? O6 C20 C21 F17' 133.5(14) . . . . ? C19 C20 C21 F17' -48.7(17) . . . . ? C2 C1 N1 N2 0.8(13) . . . . ? C2 C1 N1 Tb1 -179.8(8) . . . . ? O3 Tb1 N1 C1 -99.1(9) . . . . ? O5 Tb1 N1 C1 43.8(9) . . . . ? O6 Tb1 N1 C1 111.6(9) . . . . ? O2 Tb1 N1 C1 179.8(9) . . . . ? O4 Tb1 N1 C1 -31.5(8) . . . . ? O1 Tb1 N1 C1 -172.8(7) . . . . ? N3 Tb1 N1 C1 -7.3(11) . . . . ? O3 Tb1 N1 N2 80.2(8) . . . . ? O5 Tb1 N1 N2 -136.9(8) . . . . ? O6 Tb1 N1 N2 -69.1(8) . . . . ? O2 Tb1 N1 N2 -0.9(8) . . . . ? O4 Tb1 N1 N2 147.8(9) . . . . ? O1 Tb1 N1 N2 6.5(10) . . . . ? N3 Tb1 N1 N2 172.0(7) . . . . ? C2 C3 N2 N1 -0.2(16) . . . . ? C1 N1 N2 C3 -0.3(13) . . . . ? Tb1 N1 N2 C3 -179.8(9) . . . . ? C5 C4 N3 N4 0.2(12) . . . . ? C5 C4 N3 Tb1 177.3(8) . . . . ? O3 Tb1 N3 N4 111.6(9) . . . . ? O5 Tb1 N3 N4 -35.1(9) . . . . ? O6 Tb1 N3 N4 -104.1(9) . . . . ? O2 Tb1 N3 N4 -174.8(7) . . . . ? O4 Tb1 N3 N4 40.4(8) . . . . ? O1 Tb1 N3 N4 -172.7(9) . . . . ? N1 Tb1 N3 N4 16.5(11) . . . . ? O3 Tb1 N3 C4 -64.7(7) . . . . ? O5 Tb1 N3 C4 148.6(7) . . . . ? O6 Tb1 N3 C4 79.6(7) . . . . ? O2 Tb1 N3 C4 8.9(9) . . . . ? O4 Tb1 N3 C4 -135.9(7) . . . . ? O1 Tb1 N3 C4 11.0(7) . . . . ? N1 Tb1 N3 C4 -159.8(6) . . . . ? C4 N3 N4 C6 -0.7(12) . . . . ? Tb1 N3 N4 C6 -177.6(7) . . . . ? C5 C6 N4 N3 0.9(14) . . . . ? C9 C8 O1 Tb1 17.9(14) . . . . ? C7 C8 O1 Tb1 -161.2(7) . . . . ? O3 Tb1 O1 C8 -108.9(8) . . . . ? O5 Tb1 O1 C8 103.8(8) . . . . ? O6 Tb1 O1 C8 57.5(8) . . . . ? O2 Tb1 O1 C8 -20.8(7) . . . . ? O4 Tb1 O1 C8 -153.7(7) . . . . ? N1 Tb1 O1 C8 -28.3(10) . . . . ? N3 Tb1 O1 C8 160.5(8) . . . . ? C9 C10 O2 Tb1 -15.5(13) . . . . ? C11 C10 O2 Tb1 164.9(7) . . . . ? O3 Tb1 O2 C10 96.0(7) . . . . ? O5 Tb1 O2 C10 -104.7(7) . . . . ? O6 Tb1 O2 C10 -56.2(7) . . . . ? O4 Tb1 O2 C10 151.8(7) . . . . ? O1 Tb1 O2 C10 19.6(7) . . . . ? N1 Tb1 O2 C10 -165.0(8) . . . . ? N3 Tb1 O2 C10 21.7(9) . . . . ? C14 C13 O3 Tb1 -15.0(15) . . . . ? C12 C13 O3 Tb1 167.0(7) . . . . ? O5 Tb1 O3 C13 4.8(11) . . . . ? O6 Tb1 O3 C13 -152.5(8) . . . . ? O2 Tb1 O3 C13 157.2(9) . . . . ? O4 Tb1 O3 C13 16.8(8) . . . . ? O1 Tb1 O3 C13 -129.9(9) . . . . ? N1 Tb1 O3 C13 86.4(9) . . . . ? N3 Tb1 O3 C13 -58.7(9) . . . . ? C14 C15 O4 Tb1 11.0(15) . . . . ? C16 C15 O4 Tb1 -169.7(6) . . . . ? O3 Tb1 O4 C15 -14.8(8) . . . . ? O5 Tb1 O4 C15 157.7(9) . . . . ? O6 Tb1 O4 C15 154.6(7) . . . . ? O2 Tb1 O4 C15 -75.4(9) . . . . ? O1 Tb1 O4 C15 31.3(9) . . . . ? N1 Tb1 O4 C15 -118.2(9) . . . . ? N3 Tb1 O4 C15 75.8(8) . . . . ? C19 C18 O5 Tb1 -3.1(14) . . . . ? C17 C18 O5 Tb1 175.7(6) . . . . ? O3 Tb1 O5 C18 -160.7(7) . . . . ? O6 Tb1 O5 C18 5.6(8) . . . . ? O2 Tb1 O5 C18 55.2(9) . . . . ? O4 Tb1 O5 C18 -172.5(8) . . . . ? O1 Tb1 O5 C18 -41.1(9) . . . . ? N1 Tb1 O5 C18 112.2(8) . . . . ? N3 Tb1 O5 C18 -94.9(8) . . . . ? C19 C20 O6 Tb1 3.2(14) . . . . ? C21 C20 O6 Tb1 -179.2(8) . . . . ? O3 Tb1 O6 C20 160.2(7) . . . . ? O5 Tb1 O6 C20 -5.6(8) . . . . ? O2 Tb1 O6 C20 -147.0(8) . . . . ? O4 Tb1 O6 C20 -2.5(10) . . . . ? O1 Tb1 O6 C20 137.2(8) . . . . ? N1 Tb1 O6 C20 -80.2(8) . . . . ? N3 Tb1 O6 C20 69.6(8) . . . . ? _diffrn_measured_fraction_theta_max 0.998 _diffrn_reflns_theta_full 25.01 _diffrn_measured_fraction_theta_full 0.998 _refine_diff_density_max 0.990 _refine_diff_density_min -0.880 _refine_diff_density_rms 0.146 _database_code_depnum_ccdc_archive 'CCDC 806987' ####################################################################### # # 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_c101130d #TrackingRef 'C101130D-Ho.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C21 H11 F18 Ho N4 O6' _chemical_formula_weight 922.27 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' F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Ho Ho -0.2175 4.6783 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 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 P21/c loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y-1/2, z-1/2' _cell_length_a 8.9350(18) _cell_length_b 22.252(4) _cell_length_c 16.011(3) _cell_angle_alpha 90.00 _cell_angle_beta 97.77(3) _cell_angle_gamma 90.00 _cell_volume 3154.1(10) _cell_formula_units_Z 4 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 19164 _cell_measurement_theta_min 3.03 _cell_measurement_theta_max 27.96 _exptl_crystal_description block _exptl_crystal_colour colourless _exptl_crystal_size_max 0.20 _exptl_crystal_size_mid 0.20 _exptl_crystal_size_min 0.20 _exptl_crystal_density_meas none _exptl_crystal_density_diffrn 1.942 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1768 _exptl_absorpt_coefficient_mu 2.657 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.6186 _exptl_absorpt_correction_T_max 0.6186 _exptl_absorpt_process_details crystalclear _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 'Bruker P4' _diffrn_measurement_method '\w scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 18974 _diffrn_reflns_av_R_equivalents 0.0565 _diffrn_reflns_av_sigmaI/netI 0.0550 _diffrn_reflns_limit_h_min -10 _diffrn_reflns_limit_h_max 10 _diffrn_reflns_limit_k_min -25 _diffrn_reflns_limit_k_max 26 _diffrn_reflns_limit_l_min -19 _diffrn_reflns_limit_l_max 19 _diffrn_reflns_theta_min 3.03 _diffrn_reflns_theta_max 25.01 _reflns_number_total 5549 _reflns_number_gt 4374 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker XSCANS' _computing_cell_refinement 'Bruker XSCANS' _computing_data_reduction 'Bruker SHELXTL' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0648P)^2^+9.0696P] 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 5549 _refine_ls_number_parameters 535 _refine_ls_number_restraints 274 _refine_ls_R_factor_all 0.0826 _refine_ls_R_factor_gt 0.0602 _refine_ls_wR_factor_ref 0.1498 _refine_ls_wR_factor_gt 0.1381 _refine_ls_goodness_of_fit_ref 1.103 _refine_ls_restrained_S_all 1.203 _refine_ls_shift/su_max 0.083 _refine_ls_shift/su_mean 0.010 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group Ho1 Ho 0.90853(5) 0.156150(17) 0.24137(3) 0.05030(18) Uani 1 1 d . A . F1 F 1.1612(16) 0.0292(6) 0.0423(8) 0.110(4) Uani 0.689(9) 1 d PU A 1 F2 F 1.2454(18) -0.0021(6) 0.1645(10) 0.111(4) Uani 0.689(9) 1 d PU A 1 F3 F 1.3916(15) 0.0449(6) 0.0994(10) 0.116(4) Uani 0.689(9) 1 d PU A 1 F1' F 1.324(4) 0.0509(13) 0.0478(18) 0.105(6) Uani 0.311(9) 1 d PU A 2 F2' F 1.138(3) 0.0030(12) 0.090(2) 0.115(7) Uani 0.311(9) 1 d PDU A 2 F3' F 1.330(4) 0.0111(15) 0.172(2) 0.108(7) Uani 0.311(9) 1 d PU A 2 F4 F 1.4661(19) 0.2481(8) 0.1632(15) 0.140(5) Uani 0.619(11) 1 d PU A 3 F5 F 1.2596(16) 0.3042(6) 0.1417(10) 0.108(4) Uani 0.619(11) 1 d PU A 3 F6 F 1.3615(18) 0.2829(7) 0.2667(10) 0.117(4) Uani 0.619(11) 1 d PU A 3 F4' F 1.388(3) 0.2672(11) 0.1110(12) 0.111(6) Uani 0.381(11) 1 d PDU A 4 F5' F 1.296(3) 0.3017(13) 0.213(2) 0.125(6) Uani 0.381(11) 1 d PU A 4 F6' F 1.471(2) 0.2470(12) 0.2298(18) 0.125(6) Uani 0.381(11) 1 d PDU A 4 F7 F 1.0368(12) 0.2692(5) 0.5116(5) 0.146(3) Uani 1 1 d U . . F8 F 1.0587(14) 0.3530(5) 0.4641(7) 0.166(4) Uani 1 1 d U . . F9 F 1.2143(11) 0.2852(6) 0.4499(6) 0.161(4) Uani 1 1 d U . . F10 F 0.8659(19) 0.3550(7) 0.1052(10) 0.127(4) Uani 0.689(9) 1 d PU A 1 F11 F 0.6477(14) 0.3479(5) 0.1403(9) 0.105(4) Uani 0.689(9) 1 d PU A 1 F12 F 0.8065(19) 0.4087(5) 0.2045(9) 0.117(4) Uani 0.689(9) 1 d PU A 1 F10' F 0.748(4) 0.3366(13) 0.096(2) 0.115(7) Uani 0.311(9) 1 d PU A 2 F11' F 0.688(3) 0.3844(15) 0.2103(19) 0.134(7) Uani 0.311(9) 1 d PDU A 2 F12' F 0.891(4) 0.3958(16) 0.163(2) 0.119(7) Uani 0.311(9) 1 d PU A 2 F13 F 0.3879(13) 0.1490(5) 0.3683(7) 0.165(4) Uani 1 1 d U . . F14 F 0.5782(13) 0.1828(5) 0.4473(7) 0.157(4) Uani 1 1 d U . . F15 F 0.5093(12) 0.0967(5) 0.4649(6) 0.152(4) Uani 1 1 d U . . F16 F 0.8141(11) -0.0640(4) 0.2700(7) 0.143(3) Uani 1 1 d U . . F17 F 0.6678(14) -0.0436(4) 0.1646(7) 0.157(4) Uani 1 1 d U . . F18 F 0.5841(13) -0.0618(5) 0.2706(8) 0.176(4) Uani 1 1 d U . . C1 C 0.6886(11) 0.1938(4) 0.0556(6) 0.062(3) Uani 1 1 d . . . H1 H 0.6843 0.2332 0.0743 0.074 Uiso 1 1 calc R . . C2 C 0.6214(17) 0.1746(7) -0.0182(9) 0.111(5) Uani 1 1 d . . . H2 H 0.5629 0.1976 -0.0588 0.133 Uiso 1 1 calc R . . C3 C 0.6536(17) 0.1148(7) -0.0239(8) 0.111(5) Uani 1 1 d . . . H3 H 0.6226 0.0891 -0.0688 0.133 Uiso 1 1 calc R . . C4 C 1.0932(13) 0.0415(5) 0.3624(8) 0.078(3) Uani 1 1 d . . . H4 H 1.0875 0.0161 0.3159 0.094 Uiso 1 1 calc R . . C5 C 1.1546(16) 0.0254(6) 0.4420(9) 0.099(4) Uani 1 1 d . . . H5 H 1.1962 -0.0115 0.4597 0.119 Uiso 1 1 calc R . . C6 C 1.1422(17) 0.0741(7) 0.4888(9) 0.101(4) Uani 1 1 d . . . H6 H 1.1748 0.0776 0.5462 0.121 Uiso 1 1 calc R . . C7 C 1.2480(15) 0.0436(5) 0.1110(9) 0.085(3) Uani 1 1 d D . . C8 C 1.1933(11) 0.1004(4) 0.1502(5) 0.055(2) Uani 1 1 d . A . C9 C 1.2859(12) 0.1501(5) 0.1556(7) 0.068(3) Uani 1 1 d . . . H9 H 1.3807 0.1479 0.1379 0.082 Uiso 1 1 calc R A . C10 C 1.2375(10) 0.2035(5) 0.1872(6) 0.058(2) Uani 1 1 d . A . C11 C 1.3351(14) 0.2607(7) 0.1857(11) 0.112(6) Uani 1 1 d D . . C12 C 1.0763(17) 0.2964(6) 0.4452(9) 0.091(4) Uani 1 1 d . . . C13 C 0.9870(12) 0.2762(5) 0.3656(6) 0.065(3) Uani 1 1 d . A . C14 C 0.9289(12) 0.3190(5) 0.3081(7) 0.070(3) Uani 1 1 d . . . H14 H 0.9453 0.3594 0.3213 0.085 Uiso 1 1 calc R . . C15 C 0.8477(11) 0.3042(4) 0.2318(7) 0.060(2) Uani 1 1 d . A . C16 C 0.7889(18) 0.3541(5) 0.1709(10) 0.092(4) Uani 1 1 d D . . C17 C 0.5223(16) 0.1388(8) 0.4043(9) 0.101(5) Uani 1 1 d . . . C18 C 0.6246(11) 0.1149(5) 0.3427(7) 0.068(3) Uani 1 1 d . A . C19 C 0.6212(14) 0.0541(6) 0.3219(8) 0.083(3) Uani 1 1 d . . . H19 H 0.5583 0.0284 0.3469 0.099 Uiso 1 1 calc R . . C20 C 0.7082(12) 0.0315(5) 0.2654(7) 0.065(3) Uani 1 1 d . A . C21 C 0.6972(16) -0.0344(6) 0.2437(10) 0.100(4) Uani 1 1 d . . . N1 N 0.7621(10) 0.1505(4) 0.0993(6) 0.065(2) Uani 1 1 d . . . N2 N 0.7404(14) 0.1009(5) 0.0498(7) 0.111(4) Uani 1 1 d . . . H2A H 0.7763 0.0658 0.0632 0.133 Uiso 1 1 calc R . . N3 N 1.0432(10) 0.0968(4) 0.3594(5) 0.067(2) Uani 1 1 d . . . N4 N 1.0752(11) 0.1166(5) 0.4393(6) 0.084(3) Uani 1 1 d . . . H4A H 1.0549 0.1520 0.4560 0.101 Uiso 1 1 calc R . . O1 O 1.0657(8) 0.0960(3) 0.1729(4) 0.0641(17) Uani 1 1 d . . . O2 O 1.1157(7) 0.2124(3) 0.2152(4) 0.0612(17) Uani 1 1 d . . . O3 O 0.9748(7) 0.2204(3) 0.3581(4) 0.0625(17) Uani 1 1 d . . . O4 O 0.8160(7) 0.2526(3) 0.2025(4) 0.0565(15) Uani 1 1 d . . . O5 O 0.7035(8) 0.1543(3) 0.3155(5) 0.0670(18) Uani 1 1 d . . . O6 O 0.7994(8) 0.0590(3) 0.2282(5) 0.0695(19) 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 Ho1 0.0498(3) 0.0378(3) 0.0639(3) -0.0076(2) 0.00970(19) -0.00580(19) F1 0.139(7) 0.095(7) 0.093(6) -0.035(6) 0.001(6) 0.026(6) F2 0.129(8) 0.075(6) 0.133(7) 0.006(6) 0.030(7) 0.029(6) F3 0.100(7) 0.108(7) 0.146(8) -0.025(6) 0.043(6) 0.032(6) F1' 0.117(10) 0.102(10) 0.100(10) -0.018(8) 0.032(8) 0.020(8) F2' 0.121(10) 0.101(10) 0.124(10) -0.024(8) 0.025(8) 0.003(8) F3' 0.104(10) 0.091(10) 0.126(10) -0.003(8) 0.006(9) 0.026(9) F4 0.115(8) 0.141(8) 0.171(9) -0.012(8) 0.043(7) -0.030(7) F5 0.119(8) 0.075(6) 0.128(8) 0.021(6) 0.011(6) -0.024(6) F6 0.120(8) 0.110(8) 0.117(8) -0.022(7) -0.002(6) -0.043(6) F4' 0.119(9) 0.108(9) 0.110(9) 0.018(8) 0.028(8) -0.034(8) F5' 0.123(10) 0.109(9) 0.143(10) -0.003(9) 0.024(9) -0.020(8) F6' 0.110(9) 0.130(10) 0.131(10) 0.001(8) 0.000(8) -0.036(8) F7 0.173(7) 0.174(8) 0.085(5) -0.013(5) -0.001(5) -0.037(6) F8 0.211(8) 0.134(7) 0.136(6) -0.064(6) -0.037(6) 0.007(6) F9 0.109(6) 0.218(9) 0.146(7) -0.067(6) -0.021(5) -0.002(6) F10 0.137(8) 0.124(8) 0.126(7) 0.042(6) 0.042(7) 0.013(7) F11 0.094(6) 0.093(6) 0.119(7) 0.025(6) -0.018(6) -0.002(5) F12 0.141(8) 0.066(6) 0.139(7) -0.002(6) -0.004(7) -0.001(6) F10' 0.122(10) 0.098(10) 0.118(10) 0.014(8) -0.007(9) 0.006(9) F11' 0.132(10) 0.123(10) 0.146(10) 0.010(9) 0.010(9) 0.020(9) F12' 0.124(10) 0.107(10) 0.126(10) 0.018(8) 0.013(8) -0.012(9) F13 0.121(7) 0.232(9) 0.149(7) -0.011(6) 0.041(6) 0.042(6) F14 0.174(8) 0.161(7) 0.150(7) -0.041(6) 0.073(6) -0.035(7) F15 0.170(7) 0.172(8) 0.127(6) 0.014(6) 0.061(6) -0.029(6) F16 0.123(6) 0.076(5) 0.215(8) -0.005(5) -0.031(6) 0.014(5) F17 0.209(8) 0.091(6) 0.160(7) -0.035(6) -0.018(7) -0.022(6) F18 0.176(8) 0.102(6) 0.258(10) -0.009(6) 0.061(7) -0.056(6) C1 0.065(6) 0.044(5) 0.070(6) -0.012(5) -0.015(5) 0.012(5) C2 0.110(11) 0.118(12) 0.093(10) -0.009(9) -0.029(8) 0.038(10) C3 0.138(12) 0.108(12) 0.074(8) -0.044(8) -0.035(8) 0.025(10) C4 0.089(8) 0.050(6) 0.090(8) 0.008(6) -0.006(6) 0.006(6) C5 0.106(10) 0.065(8) 0.121(11) 0.015(8) -0.004(8) 0.009(7) C6 0.127(12) 0.095(11) 0.078(8) 0.022(8) 0.002(8) 0.004(9) C7 0.089(9) 0.063(8) 0.107(10) 0.000(7) 0.033(8) 0.018(7) C8 0.065(6) 0.049(6) 0.049(5) 0.003(4) 0.007(5) 0.015(5) C9 0.060(6) 0.071(7) 0.076(7) 0.000(6) 0.020(5) 0.004(6) C10 0.047(5) 0.063(6) 0.064(6) 0.006(5) 0.004(5) -0.005(5) C11 0.052(7) 0.107(12) 0.187(17) -0.063(12) 0.055(9) -0.013(8) C12 0.109(11) 0.073(8) 0.085(9) -0.022(7) -0.006(8) 0.006(8) C13 0.064(6) 0.065(7) 0.066(6) -0.021(6) 0.012(5) -0.011(5) C14 0.081(7) 0.039(5) 0.088(8) -0.025(6) -0.002(6) -0.012(5) C15 0.054(5) 0.041(5) 0.086(7) -0.005(5) 0.012(5) -0.002(4) C16 0.107(11) 0.051(7) 0.115(11) -0.018(7) 0.006(9) -0.006(7) C17 0.082(9) 0.135(13) 0.089(9) -0.028(9) 0.026(8) -0.048(9) C18 0.052(6) 0.077(8) 0.072(6) 0.008(6) 0.002(5) -0.011(6) C19 0.080(8) 0.071(8) 0.100(9) 0.008(7) 0.022(7) -0.025(6) C20 0.058(6) 0.045(5) 0.087(7) 0.003(5) -0.014(5) -0.011(5) C21 0.083(9) 0.073(8) 0.131(12) 0.010(9) -0.031(8) -0.026(8) N1 0.069(5) 0.050(5) 0.076(5) -0.021(4) 0.006(4) -0.002(4) N2 0.143(11) 0.068(7) 0.117(9) -0.026(6) 0.001(8) 0.016(7) N3 0.068(5) 0.060(6) 0.072(6) -0.003(4) 0.007(4) -0.009(4) N4 0.098(7) 0.087(7) 0.065(6) 0.005(5) 0.007(5) 0.009(6) O1 0.068(4) 0.045(4) 0.081(4) -0.012(3) 0.019(4) 0.004(3) O2 0.050(4) 0.056(4) 0.080(4) -0.015(3) 0.019(3) -0.006(3) O3 0.070(4) 0.056(4) 0.062(4) -0.009(3) 0.008(3) -0.008(3) O4 0.048(3) 0.046(4) 0.073(4) -0.009(3) 0.001(3) -0.002(3) O5 0.058(4) 0.051(4) 0.095(5) -0.004(4) 0.022(4) -0.007(3) O6 0.068(4) 0.047(4) 0.093(5) -0.007(4) 0.010(4) -0.017(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 Ho1 O5 2.313(7) . ? Ho1 O2 2.320(6) . ? Ho1 O1 2.321(6) . ? Ho1 O4 2.354(6) . ? Ho1 O3 2.364(6) . ? Ho1 O6 2.369(6) . ? Ho1 N1 2.469(9) . ? Ho1 N3 2.479(9) . ? F1 C7 1.297(17) . ? F2 C7 1.332(18) . ? F3 C7 1.322(16) . ? F1' C7 1.30(3) . ? F2' C7 1.345(11) . ? F3' C7 1.35(3) . ? F4 C11 1.301(19) . ? F5 C11 1.33(2) . ? F6 C11 1.38(2) . ? F4' C11 1.354(11) . ? F5' C11 1.09(3) . ? F6' C11 1.353(11) . ? F7 C12 1.312(16) . ? F8 C12 1.309(15) . ? F9 C12 1.250(15) . ? F10 C16 1.333(19) . ? F11 C16 1.297(18) . ? F12 C16 1.329(16) . ? F10' C16 1.26(3) . ? F11' C16 1.349(11) . ? F12' C16 1.32(3) . ? F13 C17 1.280(17) . ? F14 C17 1.262(15) . ? F15 C17 1.364(17) . ? F16 C21 1.258(15) . ? F17 C21 1.274(16) . ? F18 C21 1.302(16) . ? C1 N1 1.313(12) . ? C1 C2 1.321(16) . ? C1 H1 0.9300 . ? C2 C3 1.368(19) . ? C2 H2 0.9300 . ? C3 N2 1.358(16) . ? C3 H3 0.9300 . ? C4 N3 1.309(13) . ? C4 C5 1.366(16) . ? C4 H4 0.9300 . ? C5 C6 1.329(18) . ? C5 H5 0.9300 . ? C6 N4 1.324(15) . ? C6 H6 0.9300 . ? C7 C8 1.519(14) . ? C8 O1 1.246(11) . ? C8 C9 1.379(14) . ? C9 C10 1.384(14) . ? C9 H9 0.9300 . ? C10 O2 1.248(11) . ? C10 C11 1.544(17) . ? C12 C13 1.479(15) . ? C13 O3 1.250(12) . ? C13 C14 1.377(15) . ? C14 C15 1.374(14) . ? C14 H14 0.9300 . ? C15 O4 1.257(11) . ? C15 C16 1.524(17) . ? C17 C18 1.528(17) . ? C18 O5 1.241(12) . ? C18 C19 1.392(16) . ? C19 C20 1.365(16) . ? C19 H19 0.9300 . ? C20 O6 1.235(12) . ? C20 C21 1.508(16) . ? N1 N2 1.359(12) . ? N2 H2A 0.8600 . ? N3 N4 1.347(12) . ? N4 H4A 0.8600 . ? 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 O5 Ho1 O2 144.0(2) . . ? O5 Ho1 O1 143.5(2) . . ? O2 Ho1 O1 71.2(2) . . ? O5 Ho1 O4 83.0(2) . . ? O2 Ho1 O4 73.8(2) . . ? O1 Ho1 O4 128.0(2) . . ? O5 Ho1 O3 74.7(2) . . ? O2 Ho1 O3 72.3(2) . . ? O1 Ho1 O3 128.3(2) . . ? O4 Ho1 O3 72.4(2) . . ? O5 Ho1 O6 71.6(2) . . ? O2 Ho1 O6 143.7(2) . . ? O1 Ho1 O6 72.5(2) . . ? O4 Ho1 O6 133.1(2) . . ? O3 Ho1 O6 132.7(2) . . ? O5 Ho1 N1 96.5(3) . . ? O2 Ho1 N1 101.4(3) . . ? O1 Ho1 N1 79.3(3) . . ? O4 Ho1 N1 71.3(2) . . ? O3 Ho1 N1 143.5(3) . . ? O6 Ho1 N1 73.2(3) . . ? O5 Ho1 N3 86.3(3) . . ? O2 Ho1 N3 96.2(3) . . ? O1 Ho1 N3 77.9(3) . . ? O4 Ho1 N3 143.5(2) . . ? O3 Ho1 N3 71.1(3) . . ? O6 Ho1 N3 74.5(3) . . ? N1 Ho1 N3 144.8(3) . . ? N1 C1 C2 112.0(10) . . ? N1 C1 H1 124.0 . . ? C2 C1 H1 124.0 . . ? C1 C2 C3 107.5(11) . . ? C1 C2 H2 126.3 . . ? C3 C2 H2 126.3 . . ? N2 C3 C2 105.3(11) . . ? N2 C3 H3 127.3 . . ? C2 C3 H3 127.4 . . ? N3 C4 C5 111.9(12) . . ? N3 C4 H4 124.1 . . ? C5 C4 H4 124.1 . . ? C6 C5 C4 105.0(12) . . ? C6 C5 H5 127.5 . . ? C4 C5 H5 127.5 . . ? N4 C6 C5 108.1(12) . . ? N4 C6 H6 126.0 . . ? C5 C6 H6 126.0 . . ? F1 C7 F1' 71.7(16) . . ? F1 C7 F3 111.5(13) . . ? F1' C7 F3 43.2(13) . . ? F1 C7 F2 107.2(13) . . ? F1' C7 F2 130.5(17) . . ? F3 C7 F2 102.0(13) . . ? F1 C7 F3' 133.1(19) . . ? F1' C7 F3' 110(2) . . ? F3 C7 F3' 70.5(17) . . ? F2 C7 F3' 35.1(14) . . ? F1 C7 F2' 44.7(15) . . ? F1' C7 F2' 109(2) . . ? F3 C7 F2' 132.2(16) . . ? F2 C7 F2' 64.6(17) . . ? F3' C7 F2' 97(2) . . ? F1 C7 C8 111.5(11) . . ? F1' C7 C8 116.6(16) . . ? F3 C7 C8 114.4(12) . . ? F2 C7 C8 109.6(11) . . ? F3' C7 C8 108.9(17) . . ? F2' C7 C8 113.3(15) . . ? O1 C8 C9 127.6(9) . . ? O1 C8 C7 114.4(9) . . ? C9 C8 C7 118.0(10) . . ? C8 C9 C10 119.9(9) . . ? C8 C9 H9 120.0 . . ? C10 C9 H9 120.1 . . ? O2 C10 C9 126.8(9) . . ? O2 C10 C11 113.4(9) . . ? C9 C10 C11 119.8(9) . . ? F5' C11 F4 130(2) . . ? F5' C11 F5 55.8(19) . . ? F4 C11 F5 115.0(17) . . ? F5' C11 F6' 107(3) . . ? F4 C11 F6' 47.1(12) . . ? F5 C11 F6' 142.8(17) . . ? F5' C11 F4' 116(3) . . ? F4 C11 F4' 48.8(12) . . ? F5 C11 F4' 70.6(17) . . ? F6' C11 F4' 95.0(17) . . ? F5' C11 F6 48.9(18) . . ? F4 C11 F6 106.9(15) . . ? F5 C11 F6 104.3(14) . . ? F6' C11 F6 64.0(16) . . ? F4' C11 F6 139.2(16) . . ? F5' C11 C10 118.0(17) . . ? F4 C11 C10 111.0(13) . . ? F5 C11 C10 111.2(11) . . ? F6' C11 C10 106.0(16) . . ? F4' C11 C10 111.7(14) . . ? F6 C11 C10 107.8(13) . . ? F9 C12 F8 109.0(14) . . ? F9 C12 F7 103.3(13) . . ? F8 C12 F7 101.7(12) . . ? F9 C12 C13 113.8(12) . . ? F8 C12 C13 115.1(12) . . ? F7 C12 C13 112.6(12) . . ? O3 C13 C14 127.0(9) . . ? O3 C13 C12 114.6(11) . . ? C14 C13 C12 118.4(10) . . ? C15 C14 C13 122.3(9) . . ? C15 C14 H14 118.9 . . ? C13 C14 H14 118.9 . . ? O4 C15 C14 128.1(10) . . ? O4 C15 C16 112.7(9) . . ? C14 C15 C16 119.2(9) . . ? F10' C16 F11 58.0(18) . . ? F10' C16 F12' 104(2) . . ? F11 C16 F12' 133.5(18) . . ? F10' C16 F12 131.9(19) . . ? F11 C16 F12 107.8(14) . . ? F12' C16 F12 49.8(16) . . ? F10' C16 F10 50.9(17) . . ? F11 C16 F10 106.4(15) . . ? F12' C16 F10 58.1(17) . . ? F12 C16 F10 105.1(15) . . ? F10' C16 F11' 118(3) . . ? F11 C16 F11' 63.3(18) . . ? F12' C16 F11' 102(2) . . ? F12 C16 F11' 53.5(16) . . ? F10 C16 F11' 144.2(19) . . ? F10' C16 C15 114.3(16) . . ? F11 C16 C15 113.4(12) . . ? F12' C16 C15 113.1(17) . . ? F12 C16 C15 113.3(12) . . ? F10 C16 C15 110.2(12) . . ? F11' C16 C15 105.1(18) . . ? F14 C17 F13 112.7(17) . . ? F14 C17 F15 102.1(12) . . ? F13 C17 F15 106.1(12) . . ? F14 C17 C18 113.3(11) . . ? F13 C17 C18 112.3(12) . . ? F15 C17 C18 109.6(14) . . ? O5 C18 C19 126.7(11) . . ? O5 C18 C17 113.5(11) . . ? C19 C18 C17 119.8(11) . . ? C20 C19 C18 121.4(10) . . ? C20 C19 H19 119.3 . . ? C18 C19 H19 119.3 . . ? O6 C20 C19 127.4(10) . . ? O6 C20 C21 113.4(11) . . ? C19 C20 C21 119.1(11) . . ? F16 C21 F17 107.4(16) . . ? F16 C21 F18 106.9(13) . . ? F17 C21 F18 100.9(11) . . ? F16 C21 C20 114.0(10) . . ? F17 C21 C20 112.6(12) . . ? F18 C21 C20 114.0(14) . . ? C1 N1 N2 105.2(9) . . ? C1 N1 Ho1 128.3(6) . . ? N2 N1 Ho1 126.5(7) . . ? C3 N2 N1 110.0(11) . . ? C3 N2 H2A 125.0 . . ? N1 N2 H2A 125.0 . . ? C4 N3 N4 104.2(9) . . ? C4 N3 Ho1 131.1(8) . . ? N4 N3 Ho1 124.7(7) . . ? C6 N4 N3 110.8(11) . . ? C6 N4 H4A 124.6 . . ? N3 N4 H4A 124.6 . . ? C8 O1 Ho1 136.8(6) . . ? C10 O2 Ho1 137.3(6) . . ? C13 O3 Ho1 133.4(7) . . ? C15 O4 Ho1 132.9(6) . . ? C18 O5 Ho1 136.0(7) . . ? C20 O6 Ho1 134.5(7) . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag N1 C1 C2 C3 -0.5(18) . . . . ? C1 C2 C3 N2 0.6(19) . . . . ? N3 C4 C5 C6 -0.7(17) . . . . ? C4 C5 C6 N4 0.6(17) . . . . ? F1 C7 C8 O1 62.7(15) . . . . ? F1' C7 C8 O1 142(2) . . . . ? F3 C7 C8 O1 -169.6(12) . . . . ? F2 C7 C8 O1 -55.8(16) . . . . ? F3' C7 C8 O1 -93(2) . . . . ? F2' C7 C8 O1 14(2) . . . . ? F1 C7 C8 C9 -116.3(14) . . . . ? F1' C7 C8 C9 -37(2) . . . . ? F3 C7 C8 C9 11.3(18) . . . . ? F2 C7 C8 C9 125.1(13) . . . . ? F3' C7 C8 C9 88(2) . . . . ? F2' C7 C8 C9 -165(2) . . . . ? O1 C8 C9 C10 -1.9(17) . . . . ? C7 C8 C9 C10 177.0(10) . . . . ? C8 C9 C10 O2 2.2(17) . . . . ? C8 C9 C10 C11 -174.4(11) . . . . ? O2 C10 C11 F5' 5(3) . . . . ? C9 C10 C11 F5' -178(3) . . . . ? O2 C10 C11 F4 174.4(16) . . . . ? C9 C10 C11 F4 -9(2) . . . . ? O2 C10 C11 F5 -56.3(16) . . . . ? C9 C10 C11 F5 120.8(13) . . . . ? O2 C10 C11 F6' 124.8(17) . . . . ? C9 C10 C11 F6' -58(2) . . . . ? O2 C10 C11 F4' -133.0(17) . . . . ? C9 C10 C11 F4' 44(2) . . . . ? O2 C10 C11 F6 57.5(16) . . . . ? C9 C10 C11 F6 -125.4(13) . . . . ? F9 C12 C13 O3 69.8(17) . . . . ? F8 C12 C13 O3 -163.3(13) . . . . ? F7 C12 C13 O3 -47.3(16) . . . . ? F9 C12 C13 C14 -109.3(14) . . . . ? F8 C12 C13 C14 17.6(19) . . . . ? F7 C12 C13 C14 133.6(12) . . . . ? O3 C13 C14 C15 -0.4(18) . . . . ? C12 C13 C14 C15 178.5(11) . . . . ? C13 C14 C15 O4 -1.1(18) . . . . ? C13 C14 C15 C16 -179.2(11) . . . . ? O4 C15 C16 F10' -15(3) . . . . ? C14 C15 C16 F10' 164(2) . . . . ? O4 C15 C16 F11 49.5(16) . . . . ? C14 C15 C16 F11 -132.1(13) . . . . ? O4 C15 C16 F12' -133(2) . . . . ? C14 C15 C16 F12' 46(3) . . . . ? O4 C15 C16 F12 172.9(13) . . . . ? C14 C15 C16 F12 -9(2) . . . . ? O4 C15 C16 F10 -69.7(16) . . . . ? C14 C15 C16 F10 108.6(15) . . . . ? O4 C15 C16 F11' 117(2) . . . . ? C14 C15 C16 F11' -65(2) . . . . ? F14 C17 C18 O5 -31.7(19) . . . . ? F13 C17 C18 O5 97.3(14) . . . . ? F15 C17 C18 O5 -145.1(10) . . . . ? F14 C17 C18 C19 149.0(14) . . . . ? F13 C17 C18 C19 -82.0(18) . . . . ? F15 C17 C18 C19 35.7(16) . . . . ? O5 C18 C19 C20 -0.8(19) . . . . ? C17 C18 C19 C20 178.3(11) . . . . ? C18 C19 C20 O6 1.7(19) . . . . ? C18 C19 C20 C21 -178.6(11) . . . . ? O6 C20 C21 F16 68.2(17) . . . . ? C19 C20 C21 F16 -111.6(15) . . . . ? O6 C20 C21 F17 -54.5(15) . . . . ? C19 C20 C21 F17 125.7(14) . . . . ? O6 C20 C21 F18 -168.8(12) . . . . ? C19 C20 C21 F18 11.5(18) . . . . ? C2 C1 N1 N2 0.2(15) . . . . ? C2 C1 N1 Ho1 -179.5(9) . . . . ? O5 Ho1 N1 C1 78.4(9) . . . . ? O2 Ho1 N1 C1 -70.2(9) . . . . ? O1 Ho1 N1 C1 -138.3(9) . . . . ? O4 Ho1 N1 C1 -1.9(9) . . . . ? O3 Ho1 N1 C1 5.3(12) . . . . ? O6 Ho1 N1 C1 146.9(10) . . . . ? N3 Ho1 N1 C1 171.3(8) . . . . ? O5 Ho1 N1 N2 -101.3(9) . . . . ? O2 Ho1 N1 N2 110.1(9) . . . . ? O1 Ho1 N1 N2 42.0(9) . . . . ? O4 Ho1 N1 N2 178.4(10) . . . . ? O3 Ho1 N1 N2 -174.4(8) . . . . ? O6 Ho1 N1 N2 -32.8(9) . . . . ? N3 Ho1 N1 N2 -8.4(12) . . . . ? C2 C3 N2 N1 -0.4(18) . . . . ? C1 N1 N2 C3 0.1(15) . . . . ? Ho1 N1 N2 C3 179.9(9) . . . . ? C5 C4 N3 N4 0.6(14) . . . . ? C5 C4 N3 Ho1 -176.8(8) . . . . ? O5 Ho1 N3 C4 113.2(10) . . . . ? O2 Ho1 N3 C4 -102.9(10) . . . . ? O1 Ho1 N3 C4 -33.7(10) . . . . ? O4 Ho1 N3 C4 -173.9(9) . . . . ? O3 Ho1 N3 C4 -171.7(10) . . . . ? O6 Ho1 N3 C4 41.3(10) . . . . ? N1 Ho1 N3 C4 17.1(12) . . . . ? O5 Ho1 N3 N4 -63.7(8) . . . . ? O2 Ho1 N3 N4 80.3(8) . . . . ? O1 Ho1 N3 N4 149.5(8) . . . . ? O4 Ho1 N3 N4 9.3(10) . . . . ? O3 Ho1 N3 N4 11.4(8) . . . . ? O6 Ho1 N3 N4 -135.6(8) . . . . ? N1 Ho1 N3 N4 -159.8(7) . . . . ? C5 C6 N4 N3 -0.3(16) . . . . ? C4 N3 N4 C6 -0.2(13) . . . . ? Ho1 N3 N4 C6 177.4(9) . . . . ? C9 C8 O1 Ho1 -4.8(16) . . . . ? C7 C8 O1 Ho1 176.3(8) . . . . ? O5 Ho1 O1 C8 -160.6(8) . . . . ? O2 Ho1 O1 C8 6.8(9) . . . . ? O4 Ho1 O1 C8 57.0(10) . . . . ? O3 Ho1 O1 C8 -40.4(10) . . . . ? O6 Ho1 O1 C8 -171.5(9) . . . . ? N1 Ho1 O1 C8 112.9(9) . . . . ? N3 Ho1 O1 C8 -94.1(9) . . . . ? C9 C10 O2 Ho1 4.1(16) . . . . ? C11 C10 O2 Ho1 -179.1(8) . . . . ? O5 Ho1 O2 C10 160.7(8) . . . . ? O1 Ho1 O2 C10 -6.5(9) . . . . ? O4 Ho1 O2 C10 -147.4(9) . . . . ? O3 Ho1 O2 C10 136.3(9) . . . . ? O6 Ho1 O2 C10 -3.9(11) . . . . ? N1 Ho1 O2 C10 -81.0(9) . . . . ? N3 Ho1 O2 C10 68.4(9) . . . . ? C14 C13 O3 Ho1 17.3(17) . . . . ? C12 C13 O3 Ho1 -161.7(8) . . . . ? O5 Ho1 O3 C13 -107.8(9) . . . . ? O2 Ho1 O3 C13 57.6(9) . . . . ? O1 Ho1 O3 C13 104.5(9) . . . . ? O4 Ho1 O3 C13 -20.5(9) . . . . ? O6 Ho1 O3 C13 -153.5(8) . . . . ? N1 Ho1 O3 C13 -27.6(11) . . . . ? N3 Ho1 O3 C13 160.9(9) . . . . ? C14 C15 O4 Ho1 -14.2(16) . . . . ? C16 C15 O4 Ho1 164.0(8) . . . . ? O5 Ho1 O4 C15 94.9(9) . . . . ? O2 Ho1 O4 C15 -57.3(8) . . . . ? O1 Ho1 O4 C15 -106.5(9) . . . . ? O3 Ho1 O4 C15 18.8(8) . . . . ? O6 Ho1 O4 C15 151.5(8) . . . . ? N1 Ho1 O4 C15 -165.7(9) . . . . ? N3 Ho1 O4 C15 20.9(10) . . . . ? C19 C18 O5 Ho1 -13.1(17) . . . . ? C17 C18 O5 Ho1 167.7(9) . . . . ? O2 Ho1 O5 C18 -154.4(9) . . . . ? O1 Ho1 O5 C18 5.0(12) . . . . ? O4 Ho1 O5 C18 156.1(10) . . . . ? O3 Ho1 O5 C18 -130.3(10) . . . . ? O6 Ho1 O5 C18 16.1(9) . . . . ? N1 Ho1 O5 C18 85.9(10) . . . . ? N3 Ho1 O5 C18 -58.9(10) . . . . ? C19 C20 O6 Ho1 10.8(17) . . . . ? C21 C20 O6 Ho1 -168.9(7) . . . . ? O5 Ho1 O6 C20 -14.8(9) . . . . ? O2 Ho1 O6 C20 155.7(8) . . . . ? O1 Ho1 O6 C20 158.4(10) . . . . ? O4 Ho1 O6 C20 -75.6(10) . . . . ? O3 Ho1 O6 C20 31.9(10) . . . . ? N1 Ho1 O6 C20 -117.8(10) . . . . ? N3 Ho1 O6 C20 76.5(9) . . . . ? _diffrn_measured_fraction_theta_max 0.997 _diffrn_reflns_theta_full 25.01 _diffrn_measured_fraction_theta_full 0.997 _refine_diff_density_max 1.139 _refine_diff_density_min -0.665 _refine_diff_density_rms 0.123 _database_code_depnum_ccdc_archive 'CCDC 803917'