# Supplementary Material (ESI) for Chemical Communications # This journal is © The Royal Society of Chemistry 2004 data_global _journal_name_full Chem.Commun. _journal_coden_Cambridge 0182 _publ_contact_author_name 'Dr Philip Gale' _publ_contact_author_address ; School of Chemistry University of Southampton Southampton SO17 1BJ UNITED KINGDOM ; _publ_contact_author_email PHILIP.GALE@SOTON.AC.UK _publ_section_title ; Imide linked '4+4' macrocycles formed by condensation of isophthaloyl dichloride and tetra- and penta-fluoroanilines ; loop_ _publ_author_name 'Philip Gale' 'Louise S. Evans' data_s92 _database_code_depnum_ccdc_archive 'CCDC 228208' _audit_creation_method SHELXL-97 _chemical_name_systematic ; Compound 1 ; _chemical_name_common 'Compound 1' _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C57.50 H17.50 Cl4.50 F20 N4 O8' _chemical_formula_weight 1431.78 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' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 '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' _symmetry_cell_setting Monoclinic _symmetry_space_group_name_H-M C2/c loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y, -z+1/2' 'x+1/2, y+1/2, z' '-x+1/2, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y, z-1/2' '-x+1/2, -y+1/2, -z' 'x+1/2, -y+1/2, z-1/2' _cell_length_a 14.6087(5) _cell_length_b 31.9021(15) _cell_length_c 24.1559(10) _cell_angle_alpha 90.00 _cell_angle_beta 98.010(2) _cell_angle_gamma 90.00 _cell_volume 11148.0(8) _cell_formula_units_Z 8 _cell_measurement_temperature 393(2) _cell_measurement_reflns_used 79978 _cell_measurement_theta_min 2.91 _cell_measurement_theta_max 27.10 _exptl_crystal_description 'square plate' _exptl_crystal_colour colourless _exptl_crystal_size_max 0.50 _exptl_crystal_size_mid 0.30 _exptl_crystal_size_min 0.07 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.706 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 5688 _exptl_absorpt_coefficient_mu 0.365 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.8384 _exptl_absorpt_correction_T_max 0.9749 _exptl_absorpt_process_details 'SORTAV Blessing (1997)' _exptl_special_details ; PLEASE NOTE cell_measurement_ fields are not relevant to area detector data, the entire data set is used to refine the cell, which is indexed from all observed reflections in a 10 degree phi range. ; _diffrn_ambient_temperature 393(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'Nonius FR591 rotating anode' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Nonius Kappa CCD Area Detector' _diffrn_measurement_method '\f and \w scans to fill Ewald Sphere' _diffrn_detector_area_resol_mean 9.091 _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 15228 _diffrn_reflns_av_R_equivalents 0.0533 _diffrn_reflns_av_sigmaI/netI 0.0824 _diffrn_reflns_limit_h_min -16 _diffrn_reflns_limit_h_max 16 _diffrn_reflns_limit_k_min -35 _diffrn_reflns_limit_k_max 35 _diffrn_reflns_limit_l_min -26 _diffrn_reflns_limit_l_max 26 _diffrn_reflns_theta_min 3.04 _diffrn_reflns_theta_max 23.26 _reflns_number_total 7955 _reflns_number_gt 4883 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'DENZO (Otwinowski and Minor, 1997)' _computing_cell_refinement 'DENZO (Otwinowski and Minor, 1997) and COLLECT (Hooft 1998)' _computing_data_reduction 'DENZO (Otwinowski and Minor, 1997) and COLLECT (Hooft 1998)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1997a)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997b)' _computing_molecular_graphics 'PLATON (Spek, 1990)' _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^)+(0.1805P)^2^+85.6986P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment mixed _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 7955 _refine_ls_number_parameters 861 _refine_ls_number_restraints 60 _refine_ls_R_factor_all 0.1357 _refine_ls_R_factor_gt 0.0846 _refine_ls_wR_factor_ref 0.2759 _refine_ls_wR_factor_gt 0.2357 _refine_ls_goodness_of_fit_ref 0.905 _refine_ls_restrained_S_all 0.905 _refine_ls_shift/su_max 11.250 _refine_ls_shift/su_mean 0.202 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group C1 C 0.3378(5) 0.0647(2) 0.2980(3) 0.0277(17) Uani 1 1 d . . . C2 C 0.3079(5) 0.0642(2) 0.2415(3) 0.0299(18) Uani 1 1 d . . . C3 C 0.2428(5) 0.0356(3) 0.2189(3) 0.0345(19) Uani 1 1 d . . . C4 C 0.2081(5) 0.0072(2) 0.2530(3) 0.0337(19) Uani 1 1 d . . . C5 C 0.2379(5) 0.0060(2) 0.3088(3) 0.0350(19) Uani 1 1 d . . . C6 C 0.3024(5) 0.0357(2) 0.3309(3) 0.0284(17) Uani 1 1 d . . . C7 C 0.4152(5) 0.1340(2) 0.3103(3) 0.0297(18) Uani 1 1 d . . . C8 C 0.3274(5) 0.1559(2) 0.2893(3) 0.0264(17) Uani 1 1 d . . . C9 C 0.3286(5) 0.1846(3) 0.2459(3) 0.040(2) Uani 1 1 d . . . H9 H 0.3818 0.1878 0.2291 0.048 Uiso 1 1 calc R . . C10 C 0.2514(5) 0.2081(3) 0.2277(3) 0.041(2) Uani 1 1 d . . . H10 H 0.2520 0.2270 0.1985 0.049 Uiso 1 1 calc R . . C11 C 0.1734(5) 0.2035(3) 0.2530(3) 0.0361(19) Uani 1 1 d . . . H11 H 0.1215 0.2196 0.2408 0.043 Uiso 1 1 calc R . . C12 C 0.1709(5) 0.1752(2) 0.2964(3) 0.0281(17) Uani 1 1 d . . . C13 C 0.2490(5) 0.1513(2) 0.3138(3) 0.0278(17) Uani 1 1 d . . . H13 H 0.2480 0.1319 0.3425 0.033 Uiso 1 1 calc R . . C14 C 0.0880(5) 0.1749(2) 0.3240(3) 0.0291(17) Uani 1 1 d . . . C15 C 0.0030(5) 0.1450(2) 0.3921(3) 0.0273(17) Uani 1 1 d . . . C16 C -0.0917(5) 0.1383(3) 0.3779(3) 0.0330(18) Uani 1 1 d . . . C17 C -0.1517(5) 0.1480(3) 0.4141(3) 0.041(2) Uani 1 1 d . . . C18 C -0.1181(6) 0.1640(3) 0.4660(3) 0.040(2) Uani 1 1 d . . . C19 C -0.0261(6) 0.1704(2) 0.4813(3) 0.0343(19) Uani 1 1 d . . . C20 C 0.0335(5) 0.1607(2) 0.4442(3) 0.0291(17) Uani 1 1 d . . . C21 C 0.0767(4) 0.0971(2) 0.3325(3) 0.0236(16) Uani 1 1 d . . . C22 C 0.0675(5) 0.0630(2) 0.3726(3) 0.0264(17) Uani 1 1 d . . . C23 C 0.0136(5) 0.0285(2) 0.3540(3) 0.0333(18) Uani 1 1 d . . . H23 H -0.0177 0.0279 0.3177 0.040 Uiso 1 1 calc R . . C24 C 0.0072(5) -0.0048(3) 0.3897(3) 0.037(2) Uani 1 1 d . . . H24 H -0.0310 -0.0273 0.3777 0.044 Uiso 1 1 calc R . . C25 C 0.0561(5) -0.0053(2) 0.4425(3) 0.0315(18) Uani 1 1 d . . . H25 H 0.0519 -0.0282 0.4659 0.038 Uiso 1 1 calc R . . C26 C 0.1122(5) 0.0288(2) 0.4609(3) 0.0256(16) Uani 1 1 d . . . C27 C 0.1162(5) 0.0631(2) 0.4262(3) 0.0260(17) Uani 1 1 d . . . H27 H 0.1517 0.0863 0.4388 0.031 Uiso 1 1 calc R . . C28 C 0.1711(5) 0.0246(2) 0.5160(3) 0.0274(17) Uani 1 1 d . . . C29 C 0.3015(5) 0.0553(2) 0.5744(3) 0.0276(17) Uani 1 1 d . . . C30 C 0.3135(5) 0.0587(3) 0.6315(3) 0.039(2) Uani 1 1 d . . . C31 C 0.3991(7) 0.0540(3) 0.6624(3) 0.048(2) Uani 1 1 d . . . C32 C 0.4728(6) 0.0449(3) 0.6370(4) 0.046(2) Uani 1 1 d . . . C33 C 0.4632(5) 0.0397(2) 0.5801(4) 0.038(2) Uani 1 1 d . . . C34 C 0.3767(5) 0.0455(2) 0.5493(3) 0.0289(17) Uani 1 1 d . . . C35 C 0.1601(5) 0.0969(2) 0.5515(3) 0.0295(18) Uani 1 1 d . . . C36 C 0.2115(5) 0.1349(2) 0.5719(3) 0.0273(17) Uani 1 1 d . . . C37 C 0.1808(5) 0.1569(2) 0.6158(3) 0.0362(19) Uani 1 1 d . . . H37 H 0.1308 0.1469 0.6319 0.043 Uiso 1 1 calc R . . C38 C 0.2244(6) 0.1932(3) 0.6353(3) 0.042(2) Uani 1 1 d . . . H38 H 0.2052 0.2071 0.6655 0.050 Uiso 1 1 calc R . . C39 C 0.2961(5) 0.2093(3) 0.6105(3) 0.039(2) Uani 1 1 d . . . H39 H 0.3243 0.2342 0.6234 0.047 Uiso 1 1 calc R . . C40 C 0.3261(5) 0.1880(2) 0.5659(3) 0.0302(18) Uani 1 1 d . . . C41 C 0.2849(5) 0.1507(2) 0.5478(3) 0.0276(17) Uani 1 1 d . . . H41 H 0.3066 0.1360 0.5190 0.033 Uiso 1 1 calc R . . C42 C 0.3973(5) 0.2094(3) 0.5381(3) 0.0343(19) Uani 1 1 d . . . C43 C 0.4949(5) 0.2052(2) 0.4652(3) 0.0314(18) Uani 1 1 d . . . C44 C 0.5880(5) 0.2140(3) 0.4722(3) 0.0359(19) Uani 1 1 d . . . C45 C 0.6294(6) 0.2331(3) 0.4312(4) 0.043(2) Uani 1 1 d . . . C46 C 0.5745(6) 0.2446(3) 0.3820(3) 0.041(2) Uani 1 1 d . . . C47 C 0.4824(6) 0.2369(3) 0.3747(3) 0.039(2) Uani 1 1 d . . . C48 C 0.4426(5) 0.2176(2) 0.4161(3) 0.0354(19) Uani 1 1 d . . . C49 C 0.4941(5) 0.1465(2) 0.5296(3) 0.0292(17) Uani 1 1 d . . . C50 C 0.5400(5) 0.1208(2) 0.4909(3) 0.0327(18) Uani 1 1 d . . . C51 C 0.6247(5) 0.1035(3) 0.5094(3) 0.042(2) Uani 1 1 d . . . H51 H 0.6530 0.1092 0.5456 0.050 Uiso 1 1 calc R . . C52 C 0.6683(5) 0.0783(3) 0.4758(3) 0.0365(19) Uani 1 1 d . . . H52 H 0.7267 0.0676 0.4885 0.044 Uiso 1 1 calc R . . C53 C 0.6251(5) 0.0687(2) 0.4228(3) 0.0334(19) Uani 1 1 d . . . H53 H 0.6545 0.0512 0.4000 0.040 Uiso 1 1 calc R . . C54 C 0.5387(5) 0.0848(2) 0.4032(3) 0.0267(17) Uani 1 1 d . . . C55 C 0.4961(5) 0.1117(2) 0.4371(3) 0.0281(17) Uani 1 1 d . . . H55 H 0.4389 0.1236 0.4241 0.034 Uiso 1 1 calc R . . C56 C 0.4927(5) 0.0695(2) 0.3487(3) 0.0285(17) Uani 1 1 d . . . O1 O 0.4894(3) 0.15132(16) 0.3169(2) 0.0359(13) Uani 1 1 d . . . O2 O 0.0407(4) 0.20575(18) 0.3265(2) 0.0436(14) Uani 1 1 d . . . O3 O 0.4047(4) 0.24679(19) 0.5370(3) 0.0525(16) Uani 1 1 d . . . O4 O 0.4896(3) 0.13643(17) 0.5771(2) 0.0365(13) Uani 1 1 d . . . O5 O 0.0939(3) 0.09108(16) 0.2858(2) 0.0337(12) Uani 1 1 d . . . O6 O 0.0765(3) 0.09488(16) 0.5429(2) 0.0347(13) Uani 1 1 d . . . O7 O 0.1888(4) -0.00812(17) 0.5381(2) 0.0373(13) Uani 1 1 d . . . O8 O 0.5152(4) 0.03917(18) 0.3263(2) 0.0411(14) Uani 1 1 d . . . N1 N 0.4092(4) 0.09168(19) 0.3235(2) 0.0290(14) Uani 1 1 d . . . N2 N 0.0655(4) 0.13832(19) 0.3532(2) 0.0280(14) Uani 1 1 d . . . N3 N 0.2137(4) 0.06212(19) 0.5407(2) 0.0271(14) Uani 1 1 d . . . N4 N 0.4530(4) 0.18410(19) 0.5075(2) 0.0292(14) Uani 1 1 d . . . F1 F 0.3417(3) 0.09086(14) 0.20742(17) 0.0404(11) Uani 1 1 d . . . F2 F 0.2135(3) 0.03569(16) 0.16358(17) 0.0493(13) Uani 1 1 d . . . F3 F 0.1440(3) -0.02063(15) 0.23075(19) 0.0475(12) Uani 1 1 d . . . F4 F 0.2052(3) -0.02198(15) 0.34122(19) 0.0463(12) Uani 1 1 d . . . F5 F 0.3297(3) 0.03495(15) 0.38578(16) 0.0426(12) Uani 1 1 d . . . F6 F -0.1234(3) 0.12325(15) 0.32738(17) 0.0432(12) Uani 1 1 d . . . F7 F -0.2423(3) 0.14282(19) 0.3997(2) 0.0634(16) Uani 1 1 d . . . F8 F -0.1773(3) 0.17238(18) 0.5025(2) 0.0601(15) Uani 1 1 d . . . F9 F 0.0044(3) 0.18550(15) 0.53181(18) 0.0479(12) Uani 1 1 d . . . F10 F 0.1241(3) 0.16693(14) 0.45845(17) 0.0371(11) Uani 1 1 d . . . F11 F 0.2401(3) 0.06607(17) 0.65778(18) 0.0539(13) Uani 1 1 d . . . F12 F 0.4077(4) 0.0571(2) 0.7181(2) 0.085(2) Uani 1 1 d . . . F13 F 0.5573(3) 0.04180(18) 0.6664(2) 0.0676(16) Uani 1 1 d . . . F14 F 0.5354(3) 0.02968(17) 0.5553(2) 0.0574(14) Uani 1 1 d . . . F15 F 0.3681(3) 0.04207(16) 0.49450(18) 0.0494(13) Uani 1 1 d . . . F16 F 0.6404(3) 0.20347(16) 0.5199(2) 0.0495(13) Uani 1 1 d . . . F17 F 0.7194(3) 0.23975(17) 0.4370(2) 0.0608(15) Uani 1 1 d . . . F18 F 0.6138(4) 0.26284(17) 0.3415(2) 0.0622(15) Uani 1 1 d . . . F19 F 0.4308(3) 0.24789(16) 0.3266(2) 0.0549(13) Uani 1 1 d . . . F20 F 0.3523(3) 0.20947(15) 0.40825(19) 0.0463(12) Uani 1 1 d . . . C57 C 0.8851(5) 0.3358(2) 0.3168(2) 0.127(6) Uani 1 1 d DU . . H57 H 0.9301 0.3576 0.3300 0.152 Uiso 1 1 calc R . . Cl1 Cl 0.9316(3) 0.28828(11) 0.33723(17) 0.162(2) Uani 1 1 d DU . . Cl2 Cl 0.8628(4) 0.33856(18) 0.24561(15) 0.199(3) Uani 1 1 d DU . . Cl3 Cl 0.7871(3) 0.3443(2) 0.3463(2) 0.218(3) Uani 1 1 d DU . . C58 C 0.5724(7) 0.3766(3) 0.2810(3) 0.165(16) Uani 0.50 1 d PDU . . H58 H 0.6359 0.3853 0.2784 0.198 Uiso 0.50 1 calc PR . . Cl4 Cl 0.5536(5) 0.3300(2) 0.2473(3) 0.108(2) Uani 0.50 1 d PDU . . Cl5 Cl 0.5608(8) 0.3724(3) 0.3498(2) 0.169(4) Uani 0.50 1 d PDU . . Cl6 Cl 0.5000 0.4139(2) 0.2500 0.245(4) Uani 1 2 d SDU . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 C1 0.028(4) 0.026(4) 0.029(4) -0.004(3) 0.008(3) 0.001(3) C2 0.027(4) 0.037(5) 0.026(4) -0.001(4) 0.006(3) 0.004(4) C3 0.031(4) 0.046(5) 0.026(4) -0.005(4) 0.000(3) 0.005(4) C4 0.024(4) 0.034(5) 0.042(5) -0.010(4) 0.001(4) -0.003(4) C5 0.035(4) 0.034(5) 0.038(5) 0.003(4) 0.012(4) 0.004(4) C6 0.029(4) 0.029(4) 0.026(4) 0.003(3) 0.000(3) -0.001(3) C7 0.032(5) 0.038(5) 0.021(4) -0.001(3) 0.008(3) -0.002(4) C8 0.027(4) 0.029(4) 0.025(4) 0.004(3) 0.009(3) 0.003(3) C9 0.031(4) 0.046(5) 0.046(5) 0.008(4) 0.016(4) -0.001(4) C10 0.034(5) 0.049(6) 0.041(5) 0.018(4) 0.007(4) 0.004(4) C11 0.032(4) 0.040(5) 0.037(4) 0.012(4) 0.009(4) 0.006(4) C12 0.023(4) 0.032(4) 0.031(4) 0.003(3) 0.006(3) 0.000(3) C13 0.026(4) 0.027(4) 0.030(4) 0.000(3) 0.004(3) -0.002(3) C14 0.031(4) 0.030(5) 0.027(4) 0.003(3) 0.005(3) 0.003(4) C15 0.028(4) 0.024(4) 0.031(4) 0.004(3) 0.007(3) 0.007(3) C16 0.034(5) 0.039(5) 0.027(4) 0.004(4) 0.005(4) 0.001(4) C17 0.028(5) 0.053(6) 0.044(5) 0.003(4) 0.016(4) -0.002(4) C18 0.043(5) 0.042(5) 0.042(5) 0.007(4) 0.026(4) 0.009(4) C19 0.051(5) 0.031(5) 0.023(4) 0.001(3) 0.010(4) 0.008(4) C20 0.026(4) 0.029(4) 0.032(4) 0.006(3) 0.004(3) 0.005(3) C21 0.015(3) 0.029(4) 0.026(4) -0.001(3) 0.004(3) 0.002(3) C22 0.024(4) 0.026(4) 0.030(4) -0.002(3) 0.007(3) 0.005(3) C23 0.033(4) 0.038(5) 0.030(4) -0.001(4) 0.006(3) -0.002(4) C24 0.033(4) 0.042(5) 0.035(5) -0.004(4) 0.002(4) -0.014(4) C25 0.034(4) 0.028(4) 0.034(4) 0.006(3) 0.011(4) -0.001(3) C26 0.023(4) 0.025(4) 0.030(4) -0.001(3) 0.007(3) 0.001(3) C27 0.025(4) 0.025(4) 0.028(4) -0.005(3) 0.008(3) -0.001(3) C28 0.025(4) 0.031(5) 0.028(4) -0.001(3) 0.010(3) -0.002(3) C29 0.029(4) 0.027(4) 0.026(4) 0.006(3) 0.001(3) -0.001(3) C30 0.038(5) 0.045(5) 0.033(5) 0.006(4) 0.002(4) 0.007(4) C31 0.062(6) 0.049(6) 0.029(5) 0.002(4) -0.010(5) -0.001(5) C32 0.032(5) 0.043(5) 0.055(6) 0.009(4) -0.015(5) 0.003(4) C33 0.032(5) 0.026(5) 0.058(6) 0.017(4) 0.009(4) 0.002(4) C34 0.038(5) 0.022(4) 0.025(4) 0.006(3) 0.001(4) 0.004(3) C35 0.031(5) 0.036(5) 0.022(4) 0.000(3) 0.005(3) -0.004(4) C36 0.028(4) 0.026(4) 0.028(4) 0.001(3) 0.003(3) 0.005(3) C37 0.041(5) 0.036(5) 0.035(4) -0.002(4) 0.017(4) 0.003(4) C38 0.047(5) 0.044(5) 0.037(5) -0.013(4) 0.018(4) 0.002(4) C39 0.042(5) 0.035(5) 0.042(5) -0.009(4) 0.009(4) 0.003(4) C40 0.033(4) 0.031(5) 0.027(4) 0.002(3) 0.006(3) 0.001(3) C41 0.027(4) 0.029(4) 0.028(4) -0.002(3) 0.006(3) 0.003(3) C42 0.038(5) 0.030(5) 0.035(4) -0.004(4) 0.007(4) -0.004(4) C43 0.033(4) 0.025(4) 0.038(4) -0.003(3) 0.013(4) 0.000(3) C44 0.030(4) 0.037(5) 0.040(5) -0.002(4) 0.005(4) -0.002(4) C45 0.036(5) 0.043(5) 0.053(6) -0.007(4) 0.017(4) -0.002(4) C46 0.046(5) 0.035(5) 0.047(5) 0.003(4) 0.027(4) 0.001(4) C47 0.055(6) 0.032(5) 0.030(4) 0.000(4) 0.010(4) 0.007(4) C48 0.031(5) 0.027(5) 0.048(5) 0.000(4) 0.005(4) 0.000(3) C49 0.024(4) 0.027(4) 0.036(5) -0.003(4) 0.001(3) -0.001(3) C50 0.030(4) 0.034(5) 0.034(4) 0.002(4) 0.005(4) -0.001(3) C51 0.033(5) 0.054(6) 0.036(5) -0.005(4) -0.005(4) 0.001(4) C52 0.028(4) 0.037(5) 0.043(5) 0.000(4) 0.002(4) 0.008(4) C53 0.025(4) 0.033(5) 0.043(5) -0.002(4) 0.006(4) 0.003(3) C54 0.023(4) 0.023(4) 0.033(4) 0.004(3) 0.002(3) -0.003(3) C55 0.020(4) 0.032(5) 0.032(4) 0.000(3) 0.004(3) 0.001(3) C56 0.022(4) 0.034(5) 0.031(4) 0.001(4) 0.008(3) 0.006(3) O1 0.026(3) 0.034(3) 0.048(3) 0.002(2) 0.007(2) -0.004(2) O2 0.042(3) 0.038(4) 0.055(4) 0.010(3) 0.023(3) 0.013(3) O3 0.066(4) 0.033(4) 0.066(4) -0.009(3) 0.033(3) -0.007(3) O4 0.038(3) 0.044(3) 0.028(3) 0.002(3) 0.006(2) 0.003(3) O5 0.037(3) 0.041(3) 0.024(3) -0.003(2) 0.006(2) 0.001(2) O6 0.026(3) 0.035(3) 0.045(3) 0.000(2) 0.010(2) -0.001(2) O7 0.043(3) 0.027(3) 0.040(3) 0.008(3) 0.000(3) 0.005(2) O8 0.033(3) 0.040(4) 0.049(3) -0.010(3) 0.000(3) 0.007(3) N1 0.024(3) 0.031(4) 0.032(3) 0.002(3) 0.002(3) 0.002(3) N2 0.028(3) 0.031(4) 0.028(3) 0.004(3) 0.013(3) 0.002(3) N3 0.028(3) 0.030(4) 0.024(3) 0.004(3) 0.004(3) 0.001(3) N4 0.034(3) 0.025(4) 0.031(3) 0.001(3) 0.010(3) 0.001(3) F1 0.047(3) 0.047(3) 0.029(2) 0.005(2) 0.012(2) -0.002(2) F2 0.051(3) 0.063(3) 0.031(3) -0.008(2) -0.003(2) -0.005(2) F3 0.038(3) 0.049(3) 0.054(3) -0.007(2) 0.000(2) -0.008(2) F4 0.045(3) 0.045(3) 0.050(3) 0.009(2) 0.012(2) -0.008(2) F5 0.050(3) 0.052(3) 0.024(2) 0.006(2) 0.002(2) -0.006(2) F6 0.035(2) 0.059(3) 0.035(3) -0.004(2) 0.003(2) -0.007(2) F7 0.029(3) 0.094(5) 0.069(3) -0.004(3) 0.016(2) -0.005(3) F8 0.058(3) 0.076(4) 0.054(3) -0.003(3) 0.036(3) 0.016(3) F9 0.064(3) 0.049(3) 0.032(3) -0.005(2) 0.009(2) 0.009(2) F10 0.031(3) 0.038(3) 0.041(2) -0.005(2) 0.001(2) 0.007(2) F11 0.056(3) 0.078(4) 0.030(2) 0.010(2) 0.013(2) 0.015(3) F12 0.093(4) 0.123(6) 0.031(3) -0.006(3) -0.019(3) 0.028(4) F13 0.044(3) 0.073(4) 0.075(4) -0.001(3) -0.029(3) 0.002(3) F14 0.036(3) 0.066(4) 0.072(3) 0.017(3) 0.014(3) 0.015(2) F15 0.046(3) 0.070(4) 0.034(3) 0.003(2) 0.010(2) 0.023(2) F16 0.035(3) 0.062(3) 0.052(3) -0.003(3) 0.003(2) -0.011(2) F17 0.037(3) 0.067(4) 0.083(4) 0.003(3) 0.023(3) -0.012(2) F18 0.077(4) 0.051(3) 0.068(3) 0.014(3) 0.042(3) 0.004(3) F19 0.064(3) 0.054(3) 0.048(3) 0.013(2) 0.010(3) 0.007(3) F20 0.035(3) 0.050(3) 0.053(3) 0.008(2) 0.002(2) 0.000(2) C57 0.141(13) 0.115(12) 0.107(10) -0.047(9) -0.045(9) 0.042(10) Cl1 0.227(5) 0.069(2) 0.155(4) -0.031(2) -0.101(4) 0.008(3) Cl2 0.285(7) 0.185(5) 0.099(3) -0.006(3) -0.076(4) 0.013(5) Cl3 0.151(5) 0.275(8) 0.200(6) -0.106(5) -0.078(4) 0.050(5) C58 0.14(3) 0.11(3) 0.24(3) 0.02(3) 0.00(3) 0.01(3) Cl4 0.132(5) 0.098(6) 0.096(5) 0.003(5) 0.019(5) 0.013(4) Cl5 0.166(10) 0.186(11) 0.166(10) -0.048(8) 0.067(8) -0.020(8) Cl6 0.222(9) 0.195(10) 0.317(10) 0.000 0.036(8) 0.000 _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag C1 C6 1.368(10) . ? C1 C2 1.373(10) . ? C1 N1 1.424(9) . ? C2 F1 1.327(8) . ? C2 C3 1.374(11) . ? C3 F2 1.344(8) . ? C3 C4 1.370(11) . ? C4 F3 1.346(9) . ? C4 C5 1.359(11) . ? C5 F4 1.320(9) . ? C5 C6 1.388(11) . ? C6 F5 1.331(8) . ? C7 O1 1.208(9) . ? C7 N1 1.392(10) . ? C7 C8 1.487(10) . ? C8 C13 1.369(10) . ? C8 C9 1.393(10) . ? C9 C10 1.375(11) . ? C10 C11 1.373(10) . ? C11 C12 1.389(10) . ? C12 C13 1.388(10) . ? C12 C14 1.462(10) . ? C14 O2 1.209(9) . ? C14 N2 1.425(9) . ? C15 C20 1.371(10) . ? C15 C16 1.395(10) . ? C15 N2 1.414(9) . ? C16 F6 1.332(8) . ? C16 C17 1.358(11) . ? C17 F7 1.332(9) . ? C17 C18 1.378(12) . ? C18 F8 1.344(9) . ? C18 C19 1.359(12) . ? C19 F9 1.330(8) . ? C19 C20 1.369(10) . ? C20 F10 1.335(8) . ? C21 O5 1.206(8) . ? C21 N2 1.425(9) . ? C21 C22 1.476(10) . ? C22 C27 1.387(10) . ? C22 C23 1.390(11) . ? C23 C24 1.380(11) . ? C24 C25 1.373(10) . ? C25 C26 1.397(10) . ? C26 C27 1.385(10) . ? C26 C28 1.487(10) . ? C28 O7 1.185(8) . ? C28 N3 1.440(9) . ? C29 C34 1.364(10) . ? C29 C30 1.370(10) . ? C29 N3 1.436(9) . ? C30 F11 1.341(9) . ? C30 C31 1.372(12) . ? C31 F12 1.337(9) . ? C31 C32 1.346(12) . ? C32 F13 1.339(9) . ? C32 C33 1.371(12) . ? C33 F14 1.323(9) . ? C33 C34 1.387(11) . ? C34 F15 1.317(8) . ? C35 O6 1.211(8) . ? C35 N3 1.402(9) . ? C35 C36 1.474(10) . ? C36 C41 1.386(10) . ? C36 C37 1.397(10) . ? C37 C38 1.373(11) . ? C38 C39 1.376(11) . ? C39 C40 1.394(10) . ? C40 C41 1.379(10) . ? C40 C42 1.481(10) . ? C42 O3 1.200(9) . ? C42 N4 1.422(10) . ? C43 C44 1.376(11) . ? C43 C48 1.377(11) . ? C43 N4 1.430(9) . ? C44 F16 1.335(9) . ? C44 C45 1.370(11) . ? C45 F17 1.321(9) . ? C45 C46 1.387(12) . ? C46 F18 1.334(9) . ? C46 C47 1.355(12) . ? C47 F19 1.341(9) . ? C47 C48 1.370(11) . ? C48 F20 1.332(9) . ? C49 O4 1.202(9) . ? C49 N4 1.412(9) . ? C49 C50 1.474(11) . ? C50 C51 1.371(11) . ? C50 C55 1.396(10) . ? C51 C52 1.362(11) . ? C52 C53 1.381(11) . ? C53 C54 1.385(10) . ? C54 C55 1.392(10) . ? C54 C56 1.476(10) . ? C56 O8 1.178(9) . ? C56 N1 1.466(9) . ? C57 Cl1 1.706(5) . ? C57 Cl2 1.707(5) . ? C57 Cl3 1.707(5) . ? C58 Cl6 1.696(5) . ? C58 Cl4 1.699(5) . ? C58 Cl5 1.700(5) . ? Cl4 Cl4 1.591(15) 2_655 ? Cl6 C58 1.696(5) 2_655 ? 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 C6 C1 C2 118.4(7) . . ? C6 C1 N1 118.1(6) . . ? C2 C1 N1 123.3(7) . . ? F1 C2 C1 120.9(7) . . ? F1 C2 C3 118.4(6) . . ? C1 C2 C3 120.7(7) . . ? F2 C3 C4 120.4(7) . . ? F2 C3 C2 120.1(7) . . ? C4 C3 C2 119.6(7) . . ? F3 C4 C5 119.2(7) . . ? F3 C4 C3 119.4(7) . . ? C5 C4 C3 121.4(7) . . ? F4 C5 C4 120.9(7) . . ? F4 C5 C6 121.1(7) . . ? C4 C5 C6 118.0(7) . . ? F5 C6 C1 120.4(6) . . ? F5 C6 C5 117.6(6) . . ? C1 C6 C5 122.0(7) . . ? O1 C7 N1 119.8(7) . . ? O1 C7 C8 123.0(7) . . ? N1 C7 C8 117.1(6) . . ? C13 C8 C9 119.8(7) . . ? C13 C8 C7 122.3(6) . . ? C9 C8 C7 117.7(6) . . ? C10 C9 C8 120.1(7) . . ? C9 C10 C11 119.6(7) . . ? C10 C11 C12 121.1(7) . . ? C11 C12 C13 118.7(6) . . ? C11 C12 C14 117.3(7) . . ? C13 C12 C14 123.8(7) . . ? C8 C13 C12 120.7(7) . . ? O2 C14 N2 117.9(6) . . ? O2 C14 C12 122.3(7) . . ? N2 C14 C12 119.6(6) . . ? C20 C15 C16 117.8(6) . . ? C20 C15 N2 120.6(6) . . ? C16 C15 N2 121.5(6) . . ? F6 C16 C17 119.9(7) . . ? F6 C16 C15 119.2(6) . . ? C17 C16 C15 120.9(7) . . ? F7 C17 C16 120.6(7) . . ? F7 C17 C18 119.9(7) . . ? C16 C17 C18 119.4(7) . . ? F8 C18 C19 119.6(7) . . ? F8 C18 C17 119.3(7) . . ? C19 C18 C17 121.0(7) . . ? F9 C19 C18 119.8(7) . . ? F9 C19 C20 121.3(7) . . ? C18 C19 C20 118.9(7) . . ? F10 C20 C19 119.8(7) . . ? F10 C20 C15 118.3(6) . . ? C19 C20 C15 121.9(7) . . ? O5 C21 N2 121.6(6) . . ? O5 C21 C22 123.3(7) . . ? N2 C21 C22 115.2(6) . . ? C27 C22 C23 119.9(7) . . ? C27 C22 C21 121.9(6) . . ? C23 C22 C21 118.0(6) . . ? C24 C23 C22 119.4(7) . . ? C25 C24 C23 121.2(7) . . ? C24 C25 C26 119.5(7) . . ? C27 C26 C25 119.8(6) . . ? C27 C26 C28 123.0(6) . . ? C25 C26 C28 117.1(6) . . ? C22 C27 C26 120.1(7) . . ? O7 C28 N3 119.4(6) . . ? O7 C28 C26 123.1(7) . . ? N3 C28 C26 117.4(6) . . ? C34 C29 C30 117.8(7) . . ? C34 C29 N3 119.6(6) . . ? C30 C29 N3 122.5(7) . . ? F11 C30 C31 119.3(7) . . ? F11 C30 C29 119.4(7) . . ? C31 C30 C29 121.3(8) . . ? F12 C31 C32 120.5(8) . . ? F12 C31 C30 119.4(8) . . ? C32 C31 C30 120.1(8) . . ? F13 C32 C31 120.6(8) . . ? F13 C32 C33 118.8(8) . . ? C31 C32 C33 120.5(7) . . ? F14 C33 C32 120.4(7) . . ? F14 C33 C34 120.9(8) . . ? C32 C33 C34 118.7(7) . . ? F15 C34 C29 119.7(6) . . ? F15 C34 C33 118.7(7) . . ? C29 C34 C33 121.6(7) . . ? O6 C35 N3 120.2(7) . . ? O6 C35 C36 123.7(7) . . ? N3 C35 C36 116.1(6) . . ? C41 C36 C37 119.0(7) . . ? C41 C36 C35 123.2(6) . . ? C37 C36 C35 117.7(6) . . ? C38 C37 C36 120.1(7) . . ? C37 C38 C39 120.7(7) . . ? C38 C39 C40 119.7(8) . . ? C41 C40 C39 119.7(7) . . ? C41 C40 C42 123.7(7) . . ? C39 C40 C42 116.4(7) . . ? C40 C41 C36 120.7(7) . . ? O3 C42 N4 119.5(7) . . ? O3 C42 C40 122.6(7) . . ? N4 C42 C40 117.7(7) . . ? C44 C43 C48 117.8(7) . . ? C44 C43 N4 121.6(7) . . ? C48 C43 N4 120.6(6) . . ? F16 C44 C45 118.6(7) . . ? F16 C44 C43 119.4(7) . . ? C45 C44 C43 122.0(8) . . ? F17 C45 C44 121.9(8) . . ? F17 C45 C46 119.7(7) . . ? C44 C45 C46 118.4(7) . . ? F18 C46 C47 120.2(8) . . ? F18 C46 C45 119.2(7) . . ? C47 C46 C45 120.5(7) . . ? F19 C47 C46 119.6(7) . . ? F19 C47 C48 120.3(7) . . ? C46 C47 C48 120.1(7) . . ? F20 C48 C47 119.8(7) . . ? F20 C48 C43 119.1(7) . . ? C47 C48 C43 121.1(7) . . ? O4 C49 N4 120.7(7) . . ? O4 C49 C50 123.1(7) . . ? N4 C49 C50 116.1(6) . . ? C51 C50 C55 119.8(7) . . ? C51 C50 C49 119.1(7) . . ? C55 C50 C49 121.0(6) . . ? C52 C51 C50 121.2(7) . . ? C51 C52 C53 119.5(7) . . ? C52 C53 C54 120.8(7) . . ? C53 C54 C55 119.3(7) . . ? C53 C54 C56 117.5(7) . . ? C55 C54 C56 123.0(6) . . ? C54 C55 C50 119.4(6) . . ? O8 C56 N1 118.3(6) . . ? O8 C56 C54 124.1(7) . . ? N1 C56 C54 117.4(6) . . ? C7 N1 C1 123.5(6) . . ? C7 N1 C56 119.1(6) . . ? C1 N1 C56 113.9(6) . . ? C15 N2 C14 114.8(6) . . ? C15 N2 C21 119.3(6) . . ? C14 N2 C21 122.5(6) . . ? C35 N3 C29 119.4(6) . . ? C35 N3 C28 121.0(6) . . ? C29 N3 C28 114.2(6) . . ? C49 N4 C42 121.9(6) . . ? C49 N4 C43 117.9(6) . . ? C42 N4 C43 115.9(6) . . ? Cl1 C57 Cl2 110.5(4) . . ? Cl1 C57 Cl3 110.1(4) . . ? Cl2 C57 Cl3 111.1(4) . . ? Cl6 C58 Cl4 110.8(5) . . ? Cl6 C58 Cl5 110.2(5) . . ? Cl4 C58 Cl5 111.6(5) . . ? Cl4 Cl4 C58 93.2(5) 2_655 . ? C58 Cl6 C58 90.8(7) 2_655 . ? _diffrn_measured_fraction_theta_max 0.992 _diffrn_reflns_theta_full 23.26 _diffrn_measured_fraction_theta_full 0.992 _refine_diff_density_max 2.431 _refine_diff_density_min -1.701 _refine_diff_density_rms 0.099 #===END data_s92_b _database_code_depnum_ccdc_archive 'CCDC 228209' _audit_creation_method SHELXL-97 _chemical_name_systematic ; Compound 2 ; _chemical_name_common 'Compound 2' _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C58 H23 F16 N5 O8' _chemical_formula_weight 1221.81 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Monoclinic _symmetry_space_group_name_H-M P21/n loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, y+1/2, -z+1/2' '-x, -y, -z' 'x-1/2, -y-1/2, z-1/2' _cell_length_a 17.9621(5) _cell_length_b 13.2143(3) _cell_length_c 23.3857(6) _cell_angle_alpha 90.00 _cell_angle_beta 112.58 _cell_angle_gamma 90.00 _cell_volume 5125.1(2) _cell_formula_units_Z 4 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 30272 _cell_measurement_theta_min 2.91 _cell_measurement_theta_max 27.48 _exptl_crystal_description cube _exptl_crystal_colour colourless _exptl_crystal_size_max ? _exptl_crystal_size_mid ? _exptl_crystal_size_min ? _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.583 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 2456 _exptl_absorpt_coefficient_mu 0.145 _exptl_absorpt_correction_type none _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _exptl_absorpt_process_details 'SORTAV Blessing (1997)' _exptl_special_details ; PLEASE NOTE cell_measurement_ fields are not relevant to area detector data, the entire data set is used to refine the cell, which is indexed from all observed reflections in a 10 degree phi range. ; _diffrn_ambient_temperature 293(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'Nonius FR591 rotating anode' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Nonius KappaCCD Area Detector' _diffrn_measurement_method '\f and zw scans to fill Ewald Sphere' _diffrn_detector_area_resol_mean 9.091 _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 45287 _diffrn_reflns_av_R_equivalents 0.0489 _diffrn_reflns_av_sigmaI/netI 0.0442 _diffrn_reflns_limit_h_min -19 _diffrn_reflns_limit_h_max 23 _diffrn_reflns_limit_k_min -17 _diffrn_reflns_limit_k_max 15 _diffrn_reflns_limit_l_min -26 _diffrn_reflns_limit_l_max 30 _diffrn_reflns_theta_min 3.04 _diffrn_reflns_theta_max 27.51 _reflns_number_total 11319 _reflns_number_gt 7948 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'DENZO (Otwinowski and Minor, 1997)' _computing_cell_refinement 'DENZO (Otwinowski and Minor, 1997) and COLLECT (Hooft 1998)' _computing_data_reduction 'DENZO (Otwinowski and Minor, 1997) and COLLECT (Hooft 1998)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1997a)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997b)' _computing_molecular_graphics 'PLATON (Spek, 1990)' _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^)+(0.0805P)^2^+2.1534P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment mixed _refine_ls_extinction_method SHELXL _refine_ls_extinction_coef 0.0059(5) _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_number_reflns 11319 _refine_ls_number_parameters 786 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0820 _refine_ls_R_factor_gt 0.0524 _refine_ls_wR_factor_ref 0.1512 _refine_ls_wR_factor_gt 0.1344 _refine_ls_goodness_of_fit_ref 1.022 _refine_ls_restrained_S_all 1.022 _refine_ls_shift/su_max 0.007 _refine_ls_shift/su_mean 0.002 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group C1 C 0.41217(13) 0.68789(15) -0.17937(10) 0.0281(5) Uani 1 1 d . . . C2 C 0.34340(15) 0.74335(19) -0.21178(14) 0.0455(6) Uani 1 1 d . . . C3 C 0.30034(19) 0.7884(2) -0.1822(2) 0.0646(10) Uani 1 1 d . . . C4 C 0.3228(2) 0.7784(2) -0.1196(2) 0.0692(11) Uani 1 1 d . . . H4 H 0.2928 0.8087 -0.0996 0.083 Uiso 1 1 calc R . . C5 C 0.3905(2) 0.7228(2) -0.08662(14) 0.0544(8) Uani 1 1 d . . . C6 C 0.43486(14) 0.67767(17) -0.11642(11) 0.0349(5) Uani 1 1 d . . . C7 C 0.44566(12) 0.53023(15) -0.21558(9) 0.0254(4) Uani 1 1 d . . . C8 C 0.50989(12) 0.46814(15) -0.22344(9) 0.0250(4) Uani 1 1 d . . . C9 C 0.48850(13) 0.37264(16) -0.24974(10) 0.0296(5) Uani 1 1 d . . . H9 H 0.4348 0.3525 -0.2650 0.036 Uiso 1 1 calc R . . C10 C 0.54696(14) 0.30757(16) -0.25317(10) 0.0326(5) Uani 1 1 d . . . H10 H 0.5322 0.2449 -0.2723 0.039 Uiso 1 1 calc R . . C11 C 0.62722(14) 0.33537(16) -0.22829(10) 0.0316(5) Uani 1 1 d . . . H11 H 0.6667 0.2904 -0.2289 0.038 Uiso 1 1 calc R . . C12 C 0.64878(13) 0.43108(16) -0.20224(9) 0.0274(4) Uani 1 1 d . . . C13 C 0.59020(12) 0.49781(15) -0.20058(9) 0.0257(4) Uani 1 1 d . . . H7 H 0.6046 0.5623 -0.1842 0.031 Uiso 1 1 calc R . . C14 C 0.73595(13) 0.45810(15) -0.17216(10) 0.0265(4) Uani 1 1 d . . . C15 C 0.71307(12) 0.59039(16) -0.25144(10) 0.0275(4) Uani 1 1 d . . . C16 C 0.69954(14) 0.53464(17) -0.30449(11) 0.0342(5) Uani 1 1 d . . . C17 C 0.65446(16) 0.5756(2) -0.36160(11) 0.0426(6) Uani 1 1 d . . . C18 C 0.62523(15) 0.6724(2) -0.36744(12) 0.0438(6) Uani 1 1 d . . . H18 H 0.5962 0.6996 -0.4064 0.053 Uiso 1 1 calc R . . C19 C 0.63940(14) 0.72820(18) -0.31515(12) 0.0380(6) Uani 1 1 d . . . C20 C 0.68269(13) 0.68754(17) -0.25783(11) 0.0319(5) Uani 1 1 d . . . C21 C 0.83605(13) 0.59510(16) -0.16005(10) 0.0290(5) Uani 1 1 d . . . C22 C 0.86993(12) 0.59804(15) -0.09127(10) 0.0267(4) Uani 1 1 d . . . C23 C 0.82254(12) 0.59417(15) -0.05648(10) 0.0262(4) Uani 1 1 d . . . H23 H 0.7675 0.5819 -0.0757 0.031 Uiso 1 1 calc R . . C24 C 0.85739(12) 0.60866(15) 0.00713(10) 0.0256(4) Uani 1 1 d . . . C25 C 0.94059(13) 0.62423(16) 0.03612(10) 0.0303(5) Uani 1 1 d . . . H25 H 0.9641 0.6338 0.0788 0.036 Uiso 1 1 calc R . . C26 C 0.98754(13) 0.62545(17) 0.00161(11) 0.0339(5) Uani 1 1 d . . . H26 H 1.0430 0.6339 0.0211 0.041 Uiso 1 1 calc R . . C27 C 0.95247(13) 0.61415(16) -0.06193(11) 0.0320(5) Uani 1 1 d . . . H27 H 0.9843 0.6173 -0.0852 0.038 Uiso 1 1 calc R . . C28 C 0.80828(12) 0.61611(15) 0.04572(9) 0.0250(4) Uani 1 1 d . . . C29 C 0.74842(13) 0.44753(15) 0.01207(10) 0.0265(4) Uani 1 1 d . . . C30 C 0.81531(13) 0.38647(16) 0.03917(11) 0.0305(5) Uani 1 1 d . . . C31 C 0.81622(14) 0.28878(17) 0.01847(12) 0.0377(5) Uani 1 1 d . . . C32 C 0.75050(16) 0.24815(17) -0.02795(12) 0.0398(6) Uani 1 1 d . . . H32 H 0.7514 0.1821 -0.0414 0.048 Uiso 1 1 calc R . . C33 C 0.68344(15) 0.30744(18) -0.05394(11) 0.0359(5) Uani 1 1 d . . . C34 C 0.68207(13) 0.40607(17) -0.03498(10) 0.0291(5) Uani 1 1 d . . . C35 C 0.68942(13) 0.55947(16) 0.06484(10) 0.0287(5) Uani 1 1 d . . . C36 C 0.64394(12) 0.73096(15) 0.01687(9) 0.0254(4) Uani 1 1 d . . . H42 H 0.6677 0.7194 -0.0115 0.030 Uiso 1 1 calc R . . C37 C 0.65205(12) 0.66028(15) 0.06299(9) 0.0261(4) Uani 1 1 d . . . C38 C 0.61804(14) 0.67975(17) 0.10634(10) 0.0328(5) Uani 1 1 d . . . H38 H 0.6238 0.6330 0.1375 0.039 Uiso 1 1 calc R . . C39 C 0.57588(15) 0.76818(18) 0.10310(11) 0.0380(5) Uani 1 1 d . . . H39 H 0.5543 0.7813 0.1327 0.046 Uiso 1 1 calc R . . C40 C 0.56539(14) 0.83737(18) 0.05651(11) 0.0358(5) Uani 1 1 d . . . H40 H 0.5354 0.8958 0.0538 0.043 Uiso 1 1 calc R . . C41 C 0.60009(13) 0.81905(15) 0.01350(10) 0.0276(4) Uani 1 1 d . . . C43 C 0.64050(13) 0.97056(15) -0.10914(10) 0.0288(5) Uani 1 1 d . . . C44 C 0.55188(12) 0.83440(15) -0.17704(9) 0.0238(4) Uani 1 1 d . . . H44 H 0.5692 0.7887 -0.1443 0.029 Uiso 1 1 calc R . . C45 C 0.57728(12) 0.93475(15) -0.16769(9) 0.0267(4) Uani 1 1 d . . . C46 C 0.54981(14) 1.00352(16) -0.21643(10) 0.0324(5) Uani 1 1 d . . . H46 H 0.5673 1.0704 -0.2102 0.039 Uiso 1 1 calc R . . C47 C 0.49645(14) 0.97241(18) -0.27421(10) 0.0344(5) Uani 1 1 d . . . H47 H 0.4767 1.0188 -0.3064 0.041 Uiso 1 1 calc R . . C48 C 0.47256(13) 0.87253(17) -0.28393(10) 0.0305(5) Uani 1 1 d . . . H48 H 0.4376 0.8516 -0.3230 0.037 Uiso 1 1 calc R . . C49 C 0.50044(12) 0.80283(15) -0.23560(9) 0.0248(4) Uani 1 1 d . . . C50 C 0.48191(12) 0.69371(16) -0.25048(9) 0.0258(4) Uani 1 1 d . . . C51 C 0.88900(16) 0.9394(2) 0.07882(12) 0.0499(7) Uani 1 1 d . . . H51 H 0.9417 0.9461 0.1075 0.060 Uiso 1 1 calc R . . C52 C 0.82599(18) 0.9773(2) 0.09060(12) 0.0540(7) Uani 1 1 d . . . C53 C 0.74800(15) 0.97006(19) 0.04789(11) 0.0402(6) Uani 1 1 d . . . C54 C 0.73103(13) 0.91989(16) -0.00736(10) 0.0293(5) Uani 1 1 d . . . C55 C 0.79501(14) 0.87956(16) -0.01845(10) 0.0321(5) Uani 1 1 d . . . C56 C 0.87266(14) 0.89118(18) 0.02357(12) 0.0402(6) Uani 1 1 d . . . C42 C 0.58489(13) 0.89248(15) -0.03819(10) 0.0281(5) Uani 1 1 d . . . N1 N 0.45666(10) 0.63796(12) -0.21001(8) 0.0245(4) Uani 1 1 d . . . N2 N 0.75789(10) 0.55119(13) -0.19092(8) 0.0280(4) Uani 1 1 d . . . N3 N 0.65149(10) 0.91482(13) -0.05404(8) 0.0272(4) Uani 1 1 d . . . N4 N 0.74395(10) 0.54779(12) 0.03317(8) 0.0243(4) Uani 1 1 d . . . O1 O 0.38782(9) 0.49361(11) -0.20963(7) 0.0324(4) Uani 1 1 d . . . O2 O 0.48921(10) 0.65415(12) -0.29463(7) 0.0339(4) Uani 1 1 d . . . O3 O 0.86903(10) 0.63455(13) -0.19055(8) 0.0402(4) Uani 1 1 d . . . O4 O 0.78502(9) 0.40586(11) -0.13327(7) 0.0317(3) Uani 1 1 d . . . O5 O 0.68577(10) 1.03896(12) -0.10732(8) 0.0403(4) Uani 1 1 d . . . O6 O 0.51959(9) 0.93003(12) -0.06650(7) 0.0367(4) Uani 1 1 d . . . O7 O 0.67232(11) 0.48636(12) 0.08771(9) 0.0428(4) Uani 1 1 d . . . O8 O 0.82194(9) 0.67943(11) 0.08615(7) 0.0319(3) Uani 1 1 d . . . F1 F 0.31888(9) 0.75204(14) -0.27351(9) 0.0659(5) Uani 1 1 d . . . F2 F 0.23511(13) 0.84296(15) -0.21501(15) 0.1119(10) Uani 1 1 d . . . F3 F 0.41435(13) 0.71004(17) -0.02569(9) 0.0843(7) Uani 1 1 d . . . F4 F 0.50012(9) 0.62216(13) -0.08470(6) 0.0474(4) Uani 1 1 d . . . F5 F 0.72911(10) 0.44117(11) -0.30010(7) 0.0495(4) Uani 1 1 d . . . F6 F 0.63907(11) 0.51953(15) -0.41260(7) 0.0648(5) Uani 1 1 d . . . F7 F 0.60873(10) 0.82155(12) -0.31953(8) 0.0551(4) Uani 1 1 d . . . F8 F 0.69498(9) 0.74215(10) -0.20661(7) 0.0437(3) Uani 1 1 d . . . F9 F 0.87969(8) 0.42352(10) 0.08554(6) 0.0396(3) Uani 1 1 d . . . F10 F 0.88326(9) 0.23288(11) 0.04543(9) 0.0576(4) Uani 1 1 d . . . F11 F 0.61674(9) 0.27030(12) -0.09890(7) 0.0505(4) Uani 1 1 d . . . F12 F 0.61565(8) 0.46238(10) -0.06085(6) 0.0405(3) Uani 1 1 d . . . F13 F 0.93343(9) 0.85430(12) 0.00958(9) 0.0593(5) Uani 1 1 d . . . F14 F 0.78007(9) 0.83124(10) -0.07238(7) 0.0430(3) Uani 1 1 d . . . F15 F 0.68736(10) 1.01250(13) 0.05958(8) 0.0608(5) Uani 1 1 d . . . F16 F 0.83886(13) 1.0238(2) 0.14443(8) 0.0900(7) Uani 1 1 d . . . C57 C 0.3134(3) 0.0332(3) 0.7576(3) 0.124(2) Uani 1 1 d . . . H20A H 0.3558 -0.0144 0.7780 0.186 Uiso 1 1 calc R . . H20B H 0.2689 -0.0014 0.7271 0.186 Uiso 1 1 calc R . . H20C H 0.2961 0.0641 0.7876 0.186 Uiso 1 1 calc R . . C58 C 0.34325(19) 0.1108(2) 0.7277(2) 0.0740(11) Uani 1 1 d . . . N5 N 0.36765(18) 0.1700(2) 0.70514(18) 0.0793(9) Uani 1 1 d . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 C1 0.0297(11) 0.0208(10) 0.0395(12) -0.0015(9) 0.0195(10) -0.0016(8) C2 0.0375(13) 0.0334(12) 0.0732(19) 0.0158(13) 0.0299(13) 0.0043(10) C3 0.0580(18) 0.0316(14) 0.134(3) 0.0227(17) 0.069(2) 0.0134(13) C4 0.077(2) 0.0307(14) 0.141(4) -0.0166(18) 0.087(3) -0.0081(14) C5 0.076(2) 0.0491(16) 0.0640(18) -0.0302(14) 0.0555(17) -0.0346(15) C6 0.0383(12) 0.0333(12) 0.0393(12) -0.0097(10) 0.0218(11) -0.0123(10) C7 0.0267(10) 0.0261(10) 0.0224(10) -0.0021(8) 0.0084(8) -0.0035(8) C8 0.0281(10) 0.0247(10) 0.0232(10) -0.0006(8) 0.0112(8) -0.0006(8) C9 0.0306(11) 0.0274(11) 0.0295(11) -0.0036(9) 0.0101(9) -0.0044(9) C10 0.0386(12) 0.0241(10) 0.0346(11) -0.0063(9) 0.0134(10) -0.0047(9) C11 0.0367(12) 0.0260(11) 0.0353(11) -0.0017(9) 0.0174(10) 0.0028(9) C12 0.0303(11) 0.0274(10) 0.0261(10) -0.0010(9) 0.0128(9) -0.0008(8) C13 0.0297(10) 0.0235(10) 0.0259(10) -0.0037(8) 0.0131(9) -0.0028(8) C14 0.0312(11) 0.0237(10) 0.0293(10) -0.0038(9) 0.0170(9) 0.0000(9) C15 0.0266(10) 0.0308(11) 0.0284(10) 0.0013(9) 0.0140(9) -0.0010(8) C16 0.0392(12) 0.0342(12) 0.0330(12) 0.0001(10) 0.0182(10) 0.0034(10) C17 0.0448(14) 0.0567(16) 0.0286(12) -0.0008(11) 0.0167(11) 0.0010(12) C18 0.0374(13) 0.0610(17) 0.0374(13) 0.0176(12) 0.0193(11) 0.0080(12) C19 0.0329(12) 0.0374(13) 0.0521(15) 0.0146(11) 0.0255(11) 0.0066(10) C20 0.0330(11) 0.0325(11) 0.0378(12) 0.0015(10) 0.0219(10) -0.0029(9) C21 0.0273(10) 0.0287(11) 0.0345(11) -0.0003(9) 0.0160(9) -0.0008(9) C22 0.0267(10) 0.0232(10) 0.0313(11) -0.0006(9) 0.0122(9) -0.0011(8) C23 0.0235(10) 0.0240(10) 0.0307(10) -0.0006(8) 0.0100(9) -0.0003(8) C24 0.0264(10) 0.0202(9) 0.0294(10) 0.0018(8) 0.0099(9) 0.0010(8) C25 0.0272(10) 0.0296(11) 0.0306(11) 0.0003(9) 0.0071(9) -0.0029(9) C26 0.0227(10) 0.0341(12) 0.0425(13) -0.0023(10) 0.0100(10) -0.0025(9) C27 0.0280(11) 0.0302(11) 0.0416(12) 0.0010(10) 0.0178(10) -0.0006(9) C28 0.0232(10) 0.0232(10) 0.0244(10) 0.0023(8) 0.0042(8) 0.0032(8) C29 0.0307(10) 0.0239(10) 0.0287(10) 0.0000(8) 0.0158(9) 0.0000(8) C30 0.0282(11) 0.0257(10) 0.0394(12) 0.0011(9) 0.0152(10) -0.0019(9) C31 0.0364(12) 0.0284(11) 0.0580(15) 0.0048(11) 0.0290(12) 0.0060(10) C32 0.0543(15) 0.0255(11) 0.0528(14) -0.0087(11) 0.0351(13) -0.0075(11) C33 0.0435(13) 0.0355(12) 0.0341(12) -0.0074(10) 0.0207(11) -0.0136(10) C34 0.0299(11) 0.0321(11) 0.0286(10) 0.0000(9) 0.0148(9) -0.0021(9) C35 0.0346(11) 0.0261(11) 0.0282(10) 0.0014(9) 0.0152(9) 0.0012(9) C36 0.0263(10) 0.0272(10) 0.0233(9) -0.0027(8) 0.0103(8) 0.0015(8) C37 0.0276(10) 0.0248(10) 0.0269(10) -0.0021(8) 0.0114(9) -0.0005(8) C38 0.0404(12) 0.0311(11) 0.0307(11) 0.0011(9) 0.0179(10) 0.0020(10) C39 0.0475(14) 0.0380(13) 0.0380(12) -0.0022(10) 0.0270(11) 0.0072(11) C40 0.0410(13) 0.0325(12) 0.0368(12) -0.0032(10) 0.0184(10) 0.0098(10) C41 0.0302(11) 0.0244(10) 0.0273(10) -0.0023(9) 0.0102(9) 0.0027(8) C43 0.0333(11) 0.0197(10) 0.0284(10) 0.0004(8) 0.0060(9) 0.0025(9) C44 0.0246(10) 0.0235(10) 0.0221(9) 0.0040(8) 0.0075(8) 0.0002(8) C45 0.0269(10) 0.0240(10) 0.0264(10) 0.0014(8) 0.0071(8) 0.0016(8) C46 0.0359(12) 0.0241(10) 0.0332(11) 0.0052(9) 0.0089(10) 0.0000(9) C47 0.0334(11) 0.0350(12) 0.0290(11) 0.0102(9) 0.0056(9) 0.0018(10) C48 0.0268(10) 0.0354(12) 0.0250(10) 0.0029(9) 0.0050(9) -0.0022(9) C49 0.0222(9) 0.0272(10) 0.0245(10) 0.0022(8) 0.0084(8) -0.0015(8) C50 0.0231(10) 0.0308(11) 0.0216(9) 0.0002(8) 0.0067(8) -0.0018(8) C51 0.0356(13) 0.0570(17) 0.0391(14) 0.0099(13) -0.0054(11) -0.0056(12) C52 0.0560(17) 0.0668(19) 0.0281(12) -0.0111(12) 0.0039(12) -0.0145(15) C53 0.0416(13) 0.0418(13) 0.0331(12) -0.0097(10) 0.0098(11) -0.0019(11) C54 0.0335(11) 0.0238(10) 0.0248(10) 0.0010(8) 0.0048(9) 0.0000(9) C55 0.0402(12) 0.0225(10) 0.0315(11) 0.0030(9) 0.0113(10) 0.0010(9) C56 0.0326(12) 0.0331(12) 0.0496(14) 0.0138(11) 0.0098(11) 0.0052(10) C42 0.0328(11) 0.0231(10) 0.0266(10) -0.0036(8) 0.0095(9) 0.0049(9) N1 0.0264(8) 0.0246(8) 0.0248(8) -0.0014(7) 0.0123(7) -0.0012(7) N2 0.0285(9) 0.0296(9) 0.0279(9) 0.0012(7) 0.0129(8) -0.0017(7) N3 0.0299(9) 0.0215(8) 0.0248(8) 0.0008(7) 0.0044(7) 0.0011(7) N4 0.0256(8) 0.0212(8) 0.0281(9) -0.0004(7) 0.0124(7) 0.0013(7) O1 0.0322(8) 0.0297(8) 0.0398(9) -0.0047(7) 0.0187(7) -0.0062(6) O2 0.0424(9) 0.0358(8) 0.0259(8) -0.0037(7) 0.0156(7) -0.0066(7) O3 0.0369(9) 0.0510(10) 0.0387(9) 0.0038(8) 0.0212(8) -0.0087(8) O4 0.0310(8) 0.0282(8) 0.0367(8) 0.0012(7) 0.0140(7) 0.0034(6) O5 0.0466(9) 0.0249(8) 0.0367(9) 0.0040(7) 0.0019(7) -0.0095(7) O6 0.0353(9) 0.0368(9) 0.0356(8) 0.0025(7) 0.0109(7) 0.0133(7) O7 0.0638(11) 0.0271(8) 0.0553(10) 0.0078(8) 0.0425(10) 0.0049(8) O8 0.0299(8) 0.0325(8) 0.0283(8) -0.0073(7) 0.0056(6) -0.0004(6) F1 0.0384(8) 0.0766(12) 0.0763(12) 0.0422(10) 0.0149(8) 0.0113(8) F2 0.0735(13) 0.0625(12) 0.238(3) 0.0675(16) 0.1025(18) 0.0408(10) F3 0.1074(16) 0.1088(16) 0.0684(12) -0.0493(11) 0.0688(12) -0.0608(13) F4 0.0401(8) 0.0702(10) 0.0296(7) 0.0033(7) 0.0107(6) -0.0073(7) F5 0.0669(10) 0.0430(8) 0.0423(8) -0.0030(7) 0.0249(7) 0.0113(7) F6 0.0747(11) 0.0841(13) 0.0314(8) -0.0078(8) 0.0157(8) 0.0122(10) F7 0.0560(9) 0.0474(9) 0.0765(11) 0.0254(8) 0.0418(9) 0.0180(7) F8 0.0553(9) 0.0331(7) 0.0511(8) -0.0077(6) 0.0297(7) -0.0015(6) F9 0.0297(7) 0.0341(7) 0.0470(8) 0.0022(6) 0.0058(6) 0.0018(6) F10 0.0465(9) 0.0320(8) 0.0971(13) 0.0035(8) 0.0306(9) 0.0123(7) F11 0.0575(9) 0.0497(9) 0.0415(8) -0.0160(7) 0.0159(7) -0.0217(7) F12 0.0341(7) 0.0430(8) 0.0356(7) 0.0021(6) 0.0038(6) 0.0011(6) F13 0.0384(8) 0.0512(9) 0.0856(12) 0.0094(9) 0.0207(8) 0.0087(7) F14 0.0482(8) 0.0391(8) 0.0445(8) -0.0112(6) 0.0208(7) -0.0011(6) F15 0.0582(10) 0.0676(11) 0.0573(10) -0.0357(9) 0.0229(8) -0.0073(8) F16 0.0788(13) 0.1347(19) 0.0405(9) -0.0437(11) 0.0051(9) -0.0245(13) C57 0.066(3) 0.081(3) 0.234(7) 0.047(4) 0.066(3) -0.005(2) C58 0.0390(16) 0.0417(17) 0.137(3) -0.005(2) 0.0286(19) -0.0022(13) N5 0.0662(18) 0.0416(15) 0.135(3) -0.0127(17) 0.0438(19) -0.0061(13) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag C1 C6 1.375(3) . ? C1 C2 1.385(3) . ? C1 N1 1.424(3) . ? C2 F1 1.343(3) . ? C2 C3 1.358(4) . ? C3 F2 1.338(4) . ? C3 C4 1.367(5) . ? C4 C5 1.375(5) . ? C5 F3 1.332(4) . ? C5 C6 1.380(4) . ? C6 F4 1.340(3) . ? C7 O1 1.202(2) . ? C7 N1 1.436(3) . ? C7 C8 1.484(3) . ? C8 C13 1.388(3) . ? C8 C9 1.392(3) . ? C9 C10 1.383(3) . ? C10 C11 1.381(3) . ? C11 C12 1.393(3) . ? C12 C13 1.385(3) . ? C12 C14 1.493(3) . ? C14 O4 1.210(3) . ? C14 N2 1.412(3) . ? C15 C20 1.380(3) . ? C15 C16 1.382(3) . ? C15 N2 1.430(3) . ? C16 F5 1.333(3) . ? C16 C17 1.379(3) . ? C17 F6 1.339(3) . ? C17 C18 1.369(4) . ? C18 C19 1.366(4) . ? C19 F7 1.339(3) . ? C19 C20 1.375(3) . ? C20 F8 1.342(3) . ? C21 O3 1.207(3) . ? C21 N2 1.432(3) . ? C21 C22 1.486(3) . ? C22 C23 1.386(3) . ? C22 C27 1.390(3) . ? C23 C24 1.388(3) . ? C24 C25 1.399(3) . ? C24 C28 1.488(3) . ? C25 C26 1.373(3) . ? C26 C27 1.381(3) . ? C28 O8 1.215(2) . ? C28 N4 1.406(3) . ? C29 C30 1.383(3) . ? C29 C34 1.387(3) . ? C29 N4 1.427(3) . ? C30 F9 1.338(3) . ? C30 C31 1.381(3) . ? C31 F10 1.345(3) . ? C31 C32 1.370(4) . ? C32 C33 1.368(4) . ? C33 F11 1.347(3) . ? C33 C34 1.380(3) . ? C34 F12 1.337(3) . ? C35 O7 1.200(3) . ? C35 N4 1.445(3) . ? C35 C37 1.485(3) . ? C36 C41 1.391(3) . ? C36 C37 1.392(3) . ? C37 C38 1.394(3) . ? C38 C39 1.379(3) . ? C39 C40 1.379(3) . ? C40 C41 1.393(3) . ? C41 C42 1.491(3) . ? C43 O5 1.206(3) . ? C43 N3 1.431(3) . ? C43 C45 1.481(3) . ? C44 C49 1.390(3) . ? C44 C45 1.392(3) . ? C45 C46 1.392(3) . ? C46 C47 1.385(3) . ? C47 C48 1.379(3) . ? C48 C49 1.394(3) . ? C49 C50 1.491(3) . ? C50 O2 1.208(3) . ? C50 N1 1.405(3) . ? C51 C52 1.359(4) . ? C51 C56 1.368(4) . ? C52 F16 1.338(3) . ? C52 C53 1.376(4) . ? C53 F15 1.343(3) . ? C53 C54 1.378(3) . ? C54 C55 1.379(3) . ? C54 N3 1.428(3) . ? C55 F14 1.345(3) . ? C55 C56 1.372(3) . ? C56 F13 1.345(3) . ? C42 O6 1.210(3) . ? C42 N3 1.413(3) . ? C57 C58 1.455(6) . ? C58 N5 1.123(5) . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C6 C1 C2 118.2(2) . . ? C6 C1 N1 120.03(19) . . ? C2 C1 N1 121.7(2) . . ? F1 C2 C3 119.7(3) . . ? F1 C2 C1 119.3(2) . . ? C3 C2 C1 121.1(3) . . ? F2 C3 C2 119.2(4) . . ? F2 C3 C4 120.0(3) . . ? C2 C3 C4 120.7(3) . . ? C3 C4 C5 119.1(3) . . ? F3 C5 C4 121.3(3) . . ? F3 C5 C6 118.4(3) . . ? C4 C5 C6 120.3(3) . . ? F4 C6 C1 118.9(2) . . ? F4 C6 C5 120.6(2) . . ? C1 C6 C5 120.5(3) . . ? O1 C7 N1 118.92(19) . . ? O1 C7 C8 122.67(19) . . ? N1 C7 C8 118.22(17) . . ? C13 C8 C9 119.73(19) . . ? C13 C8 C7 122.58(18) . . ? C9 C8 C7 117.41(18) . . ? C10 C9 C8 120.2(2) . . ? C11 C10 C9 120.2(2) . . ? C10 C11 C12 119.7(2) . . ? C13 C12 C11 120.3(2) . . ? C13 C12 C14 120.35(18) . . ? C11 C12 C14 119.25(19) . . ? C12 C13 C8 119.84(19) . . ? O4 C14 N2 121.38(19) . . ? O4 C14 C12 123.16(19) . . ? N2 C14 C12 115.44(18) . . ? C20 C15 C16 118.2(2) . . ? C20 C15 N2 119.54(19) . . ? C16 C15 N2 122.25(19) . . ? F5 C16 C17 120.4(2) . . ? F5 C16 C15 119.8(2) . . ? C17 C16 C15 119.7(2) . . ? F6 C17 C18 119.2(2) . . ? F6 C17 C16 119.3(2) . . ? C18 C17 C16 121.5(2) . . ? C19 C18 C17 118.9(2) . . ? F7 C19 C18 120.0(2) . . ? F7 C19 C20 119.8(2) . . ? C18 C19 C20 120.2(2) . . ? F8 C20 C19 119.8(2) . . ? F8 C20 C15 118.7(2) . . ? C19 C20 C15 121.4(2) . . ? O3 C21 N2 119.1(2) . . ? O3 C21 C22 122.6(2) . . ? N2 C21 C22 118.10(18) . . ? C23 C22 C27 119.7(2) . . ? C23 C22 C21 123.09(19) . . ? C27 C22 C21 117.0(2) . . ? C22 C23 C24 119.89(19) . . ? C23 C24 C25 119.8(2) . . ? C23 C24 C28 122.07(18) . . ? C25 C24 C28 117.92(19) . . ? C26 C25 C24 120.0(2) . . ? C25 C26 C27 120.1(2) . . ? C26 C27 C22 120.4(2) . . ? O8 C28 N4 120.59(19) . . ? O8 C28 C24 121.87(19) . . ? N4 C28 C24 117.54(17) . . ? C30 C29 C34 117.63(19) . . ? C30 C29 N4 122.53(19) . . ? C34 C29 N4 119.72(18) . . ? F9 C30 C31 120.2(2) . . ? F9 C30 C29 119.11(19) . . ? C31 C30 C29 120.7(2) . . ? F10 C31 C32 120.0(2) . . ? F10 C31 C30 118.6(2) . . ? C32 C31 C30 121.4(2) . . ? C33 C32 C31 118.1(2) . . ? F11 C33 C32 120.4(2) . . ? F11 C33 C34 118.3(2) . . ? C32 C33 C34 121.3(2) . . ? F12 C34 C33 120.2(2) . . ? F12 C34 C29 118.98(19) . . ? C33 C34 C29 120.8(2) . . ? O7 C35 N4 118.83(19) . . ? O7 C35 C37 123.0(2) . . ? N4 C35 C37 117.95(17) . . ? C41 C36 C37 119.62(19) . . ? C36 C37 C38 119.68(19) . . ? C36 C37 C35 122.43(19) . . ? C38 C37 C35 117.64(19) . . ? C39 C38 C37 120.1(2) . . ? C38 C39 C40 120.7(2) . . ? C39 C40 C41 119.5(2) . . ? C36 C41 C40 120.3(2) . . ? C36 C41 C42 120.93(19) . . ? C40 C41 C42 118.61(19) . . ? O5 C43 N3 119.76(19) . . ? O5 C43 C45 122.6(2) . . ? N3 C43 C45 117.37(18) . . ? C49 C44 C45 119.63(18) . . ? C46 C45 C44 120.12(19) . . ? C46 C45 C43 116.96(19) . . ? C44 C45 C43 122.56(18) . . ? C47 C46 C45 120.0(2) . . ? C48 C47 C46 120.0(2) . . ? C47 C48 C49 120.43(19) . . ? C44 C49 C48 119.79(19) . . ? C44 C49 C50 121.65(18) . . ? C48 C49 C50 118.13(18) . . ? O2 C50 N1 121.18(19) . . ? O2 C50 C49 122.01(19) . . ? N1 C50 C49 116.80(18) . . ? C52 C51 C56 118.0(2) . . ? F16 C52 C51 120.2(2) . . ? F16 C52 C53 118.3(3) . . ? C51 C52 C53 121.5(2) . . ? F15 C53 C52 120.1(2) . . ? F15 C53 C54 119.1(2) . . ? C52 C53 C54 120.7(2) . . ? C53 C54 C55 117.5(2) . . ? C53 C54 N3 122.4(2) . . ? C55 C54 N3 119.97(19) . . ? F14 C55 C56 120.4(2) . . ? F14 C55 C54 118.63(19) . . ? C56 C55 C54 120.9(2) . . ? F13 C56 C51 119.9(2) . . ? F13 C56 C55 118.8(2) . . ? C51 C56 C55 121.3(2) . . ? O6 C42 N3 120.75(19) . . ? O6 C42 C41 123.2(2) . . ? N3 C42 C41 116.02(17) . . ? C50 N1 C1 119.00(17) . . ? C50 N1 C7 121.83(17) . . ? C1 N1 C7 114.88(17) . . ? C14 N2 C15 120.32(17) . . ? C14 N2 C21 122.21(17) . . ? C15 N2 C21 114.99(17) . . ? C42 N3 C54 120.57(17) . . ? C42 N3 C43 120.40(17) . . ? C54 N3 C43 114.57(17) . . ? C28 N4 C29 121.17(17) . . ? C28 N4 C35 119.27(17) . . ? C29 N4 C35 114.57(16) . . ? N5 C58 C57 178.7(4) . . ? _diffrn_measured_fraction_theta_max 0.961 _diffrn_reflns_theta_full 27.51 _diffrn_measured_fraction_theta_full 0.961 _refine_diff_density_max 1.427 _refine_diff_density_min -0.499 _refine_diff_density_rms 0.059