# Supplementary Material (ESI) for Organic & Biomolecular Chemistry # This journal is © The Royal Society of Chemistry 2003 data_global _journal_name_full ? _journal_coden_Cambridge 177 _journal_year ? _journal_volume ? _journal_page_first ? loop_ _publ_author_name 'Chambers, Richard D.' 'Hoskin, Philip R.' 'Kenwright, Alan R.' 'Khalil, Ali' 'Richmond, Paul' 'Sandford, Graham' 'Yufit, Dmitrii S.' 'Howard, Judith A.K.' _publ_contact_author_address ; Chemistry Department, University of Durham, South Rd., Durham DH1 3LE UK ; _publ_contact_author_email d.s.yufit@durham.ac.uk _publ_contact_author_name 'Dr. D.S.Yufit' _publ_contact_letter ; The CIF file contains data for the structure 6a from the paper "Polyhalogenated Heterocyclic Compounds. Part 50. Macrocycles from Perfluoro-4-isopropylpyridine" by R.D.Chambers, P.R.Hoskin, A.R.Kenwright, A.Khalil, P.Richmond, G.Sandford, D.S.Yufit and J.A.K.Howard The paper will be submitted to J.Org.Biomol.Chem. (former J.Chem.Soc. Perkin Trans. 1&2) ; _publ_requested_journal J.Org.Biomol.Chem data_s170s _database_code_CSD 197403 _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C24 H16 F18 N2 O6' _chemical_formula_weight 770.39 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' 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' _symmetry_cell_setting triclinic _symmetry_space_group_name_H-M 'P -1' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 10.771(1) _cell_length_b 11.765(1) _cell_length_c 12.279(1) _cell_angle_alpha 69.53(1) _cell_angle_beta 85.10(1) _cell_angle_gamma 85.96(1) _cell_volume 1451.0(2) _cell_formula_units_Z 2 _cell_measurement_temperature 120.0(2) _cell_measurement_reflns_used 1575 _cell_measurement_theta_min 2.5 _cell_measurement_theta_max 23.8 _exptl_crystal_description plate _exptl_crystal_colour colourless _exptl_crystal_size_max 0.32 _exptl_crystal_size_mid 0.18 _exptl_crystal_size_min 0.04 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.763 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 768 _exptl_absorpt_coefficient_mu 0.199 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.9389 _exptl_absorpt_correction_T_max 0.9921 _exptl_absorpt_process_details 'SADABS (Sheldrick,1997)' _exptl_special_details ; ? ; _diffrn_ambient_temperature 120(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 SMART CCD' _diffrn_measurement_method \w-scan _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% 0 _diffrn_reflns_number 11550 _diffrn_reflns_av_R_equivalents 0.0878 _diffrn_reflns_av_sigmaI/netI 0.1688 _diffrn_reflns_limit_h_min -13 _diffrn_reflns_limit_h_max 13 _diffrn_reflns_limit_k_min -15 _diffrn_reflns_limit_k_max 13 _diffrn_reflns_limit_l_min -15 _diffrn_reflns_limit_l_max 13 _diffrn_reflns_theta_min 1.77 _diffrn_reflns_theta_max 27.50 _reflns_number_total 6561 _reflns_number_gt 2734 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SMART' _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^)+(0.0800P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens difmap _refine_ls_hydrogen_treatment mixed _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 6561 _refine_ls_number_parameters 512 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.2019 _refine_ls_R_factor_gt 0.0762 _refine_ls_wR_factor_ref 0.1921 _refine_ls_wR_factor_gt 0.1519 _refine_ls_goodness_of_fit_ref 0.952 _refine_ls_restrained_S_all 0.952 _refine_ls_shift/su_max 0.001 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group O1 O 0.0334(3) -0.0006(3) 0.2671(3) 0.0271(9) Uani 1 1 d . . . O2 O 0.1497(3) -0.1301(3) 0.4809(3) 0.0255(9) Uani 1 1 d . . . O3 O 0.2845(3) 0.0053(3) 0.5931(3) 0.0237(8) Uani 1 1 d . . . O4 O 0.4629(3) 0.0366(3) 0.2244(3) 0.0235(8) Uani 1 1 d . . . O5 O 0.3768(3) -0.1369(3) 0.1245(3) 0.0208(8) Uani 1 1 d . . . O6 O 0.2136(3) -0.0624(3) -0.0688(3) 0.0254(9) Uani 1 1 d . . . N1 N 0.1188(4) -0.0343(4) 0.0994(4) 0.0215(10) Uani 1 1 d . . . N2 N 0.3776(4) 0.0179(4) 0.4099(4) 0.0220(10) Uani 1 1 d . . . C1 C 0.1659(5) 0.0129(5) -0.0113(4) 0.0197(11) Uani 1 1 d . . . C2 C 0.1652(5) 0.1358(5) -0.0703(4) 0.0201(12) Uani 1 1 d . . . C3 C 0.1155(4) 0.2191(5) -0.0198(4) 0.0214(12) Uani 1 1 d . . . C4 C 0.0685(5) 0.1674(5) 0.0967(5) 0.0242(12) Uani 1 1 d . . . C5 C 0.0744(4) 0.0412(5) 0.1537(5) 0.0219(12) Uani 1 1 d . . . C6 C 0.0349(6) -0.1306(5) 0.3251(5) 0.0272(13) Uani 1 1 d . . . C7 C 0.0321(6) -0.1565(6) 0.4548(5) 0.0300(14) Uani 1 1 d . . . C8 C 0.1601(5) -0.1664(5) 0.6035(5) 0.0238(12) Uani 1 1 d . . . C9 C 0.2825(6) -0.1275(5) 0.6252(5) 0.0270(13) Uani 1 1 d . . . C10 C 0.3292(4) 0.0713(5) 0.4852(4) 0.0218(12) Uani 1 1 d . . . C11 C 0.3235(5) 0.1968(5) 0.4546(4) 0.0198(11) Uani 1 1 d . . . C12 C 0.3706(5) 0.2727(5) 0.3465(4) 0.0203(11) Uani 1 1 d . . . C13 C 0.4160(5) 0.2124(5) 0.2707(4) 0.0219(12) Uani 1 1 d . . . C14 C 0.4178(4) 0.0873(4) 0.3044(4) 0.0189(11) Uani 1 1 d . . . C15 C 0.4854(6) -0.0948(5) 0.2669(5) 0.0232(12) Uani 1 1 d . . . C16 C 0.4962(5) -0.1375(5) 0.1645(5) 0.0222(12) Uani 1 1 d . . . C17 C 0.3774(5) -0.1961(5) 0.0416(5) 0.0203(12) Uani 1 1 d . . . C18 C 0.2477(5) -0.1874(5) 0.0016(5) 0.0242(12) Uani 1 1 d . . . C19 C 0.1124(5) 0.3565(5) -0.0764(5) 0.0253(13) Uani 1 1 d . . . C20 C 0.1033(6) 0.4095(5) -0.2099(5) 0.0334(14) Uani 1 1 d . . . C21 C 0.2196(5) 0.4108(5) -0.0390(5) 0.0265(13) Uani 1 1 d . . . C22 C 0.3791(5) 0.4097(5) 0.3153(4) 0.0207(12) Uani 1 1 d . . . C23 C 0.5018(5) 0.4373(5) 0.3516(5) 0.0272(13) Uani 1 1 d . . . C24 C 0.2655(5) 0.4761(5) 0.3606(5) 0.0329(14) Uani 1 1 d . . . F1 F 0.2151(3) 0.1752(3) -0.1825(2) 0.0250(7) Uani 1 1 d . . . F2 F 0.0198(3) 0.2362(3) 0.1588(3) 0.0353(8) Uani 1 1 d . . . F3 F 0.0011(3) 0.4039(3) -0.0383(3) 0.0323(8) Uani 1 1 d . . . F4 F 0.0248(3) 0.3484(3) -0.2455(3) 0.0356(8) Uani 1 1 d . . . F5 F 0.0624(3) 0.5253(3) -0.2440(3) 0.0391(9) Uani 1 1 d . . . F6 F 0.2152(3) 0.4070(3) -0.2688(3) 0.0364(8) Uani 1 1 d . . . F7 F 0.2095(3) 0.3870(3) 0.0754(3) 0.0414(9) Uani 1 1 d . . . F8 F 0.2237(3) 0.5311(3) -0.0906(3) 0.0380(9) Uani 1 1 d . . . F9 F 0.3284(3) 0.3619(3) -0.0657(3) 0.0379(9) Uani 1 1 d . . . F10 F 0.2774(3) 0.2429(3) 0.5384(2) 0.0278(7) Uani 1 1 d . . . F11 F 0.4685(3) 0.2751(3) 0.1628(2) 0.0307(8) Uani 1 1 d . . . F12 F 0.3816(3) 0.4662(3) 0.1956(3) 0.0344(8) Uani 1 1 d . . . F13 F 0.5181(3) 0.3759(3) 0.4642(3) 0.0368(8) Uani 1 1 d . . . F14 F 0.5133(3) 0.5552(3) 0.3301(3) 0.0351(8) Uani 1 1 d . . . F15 F 0.5984(3) 0.4001(3) 0.2919(3) 0.0390(9) Uani 1 1 d . . . F16 F 0.2576(3) 0.5922(3) 0.2915(3) 0.0457(10) Uani 1 1 d . . . F17 F 0.2820(3) 0.4764(3) 0.4678(3) 0.0405(9) Uani 1 1 d . . . F18 F 0.1613(3) 0.4246(3) 0.3629(3) 0.0435(9) Uani 1 1 d . . . H61 H 0.106(5) -0.166(4) 0.302(4) 0.010(12) Uiso 1 1 d . . . H62 H -0.030(6) -0.152(6) 0.305(6) 0.05(2) Uiso 1 1 d . . . H71 H 0.024(5) -0.239(5) 0.487(5) 0.025 Uiso 1 1 d . . . H72 H -0.031(5) -0.103(5) 0.470(4) 0.025 Uiso 1 1 d . . . H81 H 0.165(5) -0.256(5) 0.635(4) 0.025 Uiso 1 1 d . . . H82 H 0.102(5) -0.123(5) 0.626(4) 0.021(15) Uiso 1 1 d . . . H91 H 0.299(5) -0.156(5) 0.707(5) 0.035(16) Uiso 1 1 d . . . H92 H 0.346(6) -0.155(5) 0.588(6) 0.05(2) Uiso 1 1 d . . . H151 H 0.423(5) -0.130(4) 0.301(4) 0.005(12) Uiso 1 1 d . . . H152 H 0.566(5) -0.117(4) 0.316(4) 0.024(14) Uiso 1 1 d . . . H171 H 0.425(6) -0.157(5) -0.015(5) 0.039(18) Uiso 1 1 d . . . H172 H 0.404(4) -0.296(4) 0.083(4) 0.013(12) Uiso 1 1 d . . . H161 H 0.550(5) -0.090(4) 0.104(4) 0.019(13) Uiso 1 1 d . . . H162 H 0.532(5) -0.225(5) 0.193(4) 0.020(13) Uiso 1 1 d . . . H181 H 0.239(5) -0.227(5) -0.054(5) 0.024(14) Uiso 1 1 d . . . H182 H 0.179(6) -0.223(5) 0.062(5) 0.047(18) Uiso 1 1 d . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 O1 0.031(2) 0.030(2) 0.020(2) -0.0116(17) 0.0057(16) 0.0045(17) O2 0.022(2) 0.040(2) 0.017(2) -0.0122(17) 0.0034(15) -0.0093(17) O3 0.032(2) 0.024(2) 0.0154(19) -0.0084(16) 0.0067(16) -0.0066(16) O4 0.025(2) 0.025(2) 0.022(2) -0.0110(17) 0.0034(15) -0.0013(16) O5 0.0125(19) 0.033(2) 0.024(2) -0.0202(17) 0.0011(14) 0.0046(15) O6 0.025(2) 0.029(2) 0.027(2) -0.0170(17) 0.0027(16) 0.0060(16) N1 0.019(2) 0.027(2) 0.020(2) -0.011(2) 0.0015(18) -0.0006(19) N2 0.019(2) 0.027(2) 0.020(3) -0.009(2) 0.0012(18) -0.0043(19) C1 0.016(3) 0.031(3) 0.018(3) -0.017(2) 0.000(2) 0.004(2) C2 0.014(3) 0.033(3) 0.016(3) -0.014(2) 0.005(2) 0.001(2) C3 0.011(3) 0.032(3) 0.023(3) -0.013(2) 0.002(2) 0.003(2) C4 0.021(3) 0.035(3) 0.023(3) -0.020(3) 0.006(2) 0.003(2) C5 0.007(3) 0.036(3) 0.025(3) -0.015(3) 0.005(2) -0.001(2) C6 0.023(4) 0.032(4) 0.031(3) -0.016(3) 0.002(3) -0.004(3) C7 0.025(3) 0.031(3) 0.032(4) -0.009(3) 0.006(3) -0.007(3) C8 0.021(3) 0.025(3) 0.024(3) -0.010(3) 0.009(2) 0.002(2) C9 0.036(4) 0.030(3) 0.015(3) -0.007(3) -0.001(3) 0.003(3) C10 0.013(3) 0.035(3) 0.020(3) -0.014(2) 0.005(2) -0.005(2) C11 0.020(3) 0.024(3) 0.020(3) -0.015(2) 0.003(2) 0.000(2) C12 0.021(3) 0.024(3) 0.018(3) -0.009(2) 0.000(2) -0.006(2) C13 0.022(3) 0.027(3) 0.013(3) -0.003(2) 0.001(2) -0.008(2) C14 0.009(3) 0.025(3) 0.025(3) -0.012(2) -0.003(2) 0.000(2) C15 0.017(3) 0.028(3) 0.030(3) -0.015(3) -0.003(3) -0.004(2) C16 0.011(3) 0.027(3) 0.028(3) -0.011(3) 0.004(2) 0.002(2) C17 0.018(3) 0.023(3) 0.022(3) -0.012(2) 0.008(2) -0.002(2) C18 0.026(3) 0.023(3) 0.031(3) -0.020(3) 0.005(3) -0.002(2) C19 0.014(3) 0.035(3) 0.033(3) -0.022(3) 0.006(2) -0.001(2) C20 0.029(3) 0.026(3) 0.045(4) -0.013(3) -0.003(3) -0.001(3) C21 0.022(3) 0.026(3) 0.035(4) -0.017(3) 0.001(2) 0.003(2) C22 0.023(3) 0.022(3) 0.018(3) -0.009(2) -0.001(2) 0.004(2) C23 0.025(3) 0.026(3) 0.028(3) -0.009(3) 0.008(2) -0.002(2) C24 0.029(4) 0.028(3) 0.039(4) -0.011(3) 0.005(3) 0.002(3) F1 0.0234(17) 0.0348(18) 0.0164(16) -0.0104(13) 0.0058(12) 0.0011(13) F2 0.040(2) 0.0363(19) 0.034(2) -0.0231(16) 0.0154(15) 0.0019(15) F3 0.0206(18) 0.0318(18) 0.044(2) -0.0156(16) 0.0083(14) 0.0062(13) F4 0.032(2) 0.0350(19) 0.041(2) -0.0130(16) -0.0079(15) -0.0030(15) F5 0.045(2) 0.0270(19) 0.042(2) -0.0086(16) -0.0044(16) 0.0017(16) F6 0.035(2) 0.042(2) 0.032(2) -0.0132(16) 0.0109(15) -0.0093(16) F7 0.046(2) 0.061(2) 0.027(2) -0.0266(17) 0.0022(15) -0.0129(18) F8 0.034(2) 0.036(2) 0.049(2) -0.0213(17) 0.0045(16) -0.0106(15) F9 0.0174(18) 0.048(2) 0.055(2) -0.0271(18) 0.0009(15) 0.0013(15) F10 0.0297(18) 0.0325(18) 0.0247(17) -0.0166(14) 0.0069(13) 0.0009(14) F11 0.043(2) 0.0276(17) 0.0193(17) -0.0075(14) 0.0122(14) -0.0058(14) F12 0.052(2) 0.0302(18) 0.0211(18) -0.0091(14) -0.0030(15) -0.0016(15) F13 0.036(2) 0.045(2) 0.033(2) -0.0154(16) -0.0108(15) -0.0047(16) F14 0.034(2) 0.0273(18) 0.050(2) -0.0220(16) 0.0062(16) -0.0068(14) F15 0.0217(18) 0.039(2) 0.057(2) -0.0196(18) 0.0121(16) -0.0046(14) F16 0.041(2) 0.0240(19) 0.058(2) -0.0019(17) 0.0076(18) 0.0103(15) F17 0.045(2) 0.039(2) 0.041(2) -0.0234(17) 0.0135(17) -0.0013(16) F18 0.0146(18) 0.041(2) 0.069(3) -0.0133(19) 0.0003(16) 0.0014(15) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag O1 C5 1.350(6) . ? O1 C6 1.443(7) . ? O2 C7 1.414(7) . ? O2 C8 1.426(6) . ? O3 C10 1.347(6) . ? O3 C9 1.473(7) . ? O4 C14 1.359(6) . ? O4 C15 1.457(6) . ? O5 C16 1.414(6) . ? O5 C17 1.419(6) . ? O6 C1 1.363(6) . ? O6 C18 1.461(6) . ? N1 C5 1.327(6) . ? N1 C1 1.345(6) . ? N2 C14 1.321(6) . ? N2 C10 1.342(6) . ? C1 C2 1.373(7) . ? C2 F1 1.366(5) . ? C2 C3 1.387(7) . ? C3 C4 1.409(7) . ? C3 C19 1.519(8) . ? C4 F2 1.347(6) . ? C4 C5 1.401(7) . ? C6 C7 1.511(8) . ? C8 C9 1.500(8) . ? C10 C11 1.388(7) . ? C11 F10 1.365(5) . ? C11 C12 1.391(7) . ? C12 C13 1.393(7) . ? C12 C22 1.529(7) . ? C13 F11 1.367(5) . ? C13 C14 1.381(7) . ? C15 C16 1.501(7) . ? C17 C18 1.505(8) . ? C19 F3 1.400(6) . ? C19 C21 1.533(8) . ? C19 C20 1.546(8) . ? C20 F5 1.331(6) . ? C20 F4 1.339(7) . ? C20 F6 1.355(7) . ? C21 F7 1.329(6) . ? C21 F9 1.336(6) . ? C21 F8 1.335(6) . ? C22 F12 1.384(6) . ? C22 C23 1.521(8) . ? C22 C24 1.572(7) . ? C23 F14 1.331(6) . ? C23 F13 1.337(6) . ? C23 F15 1.358(6) . ? C24 F18 1.306(7) . ? C24 F16 1.334(6) . ? C24 F17 1.344(7) . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C5 O1 C6 117.3(4) . . ? C7 O2 C8 111.4(4) . . ? C10 O3 C9 118.7(4) . . ? C14 O4 C15 116.6(4) . . ? C16 O5 C17 112.9(4) . . ? C1 O6 C18 117.3(4) . . ? C5 N1 C1 118.5(4) . . ? C14 N2 C10 118.6(4) . . ? N1 C1 O6 119.9(5) . . ? N1 C1 C2 121.9(5) . . ? O6 C1 C2 118.2(4) . . ? F1 C2 C1 117.7(4) . . ? F1 C2 C3 120.0(4) . . ? C1 C2 C3 122.3(5) . . ? C2 C3 C4 114.7(5) . . ? C2 C3 C19 126.4(5) . . ? C4 C3 C19 118.9(5) . . ? F2 C4 C5 117.4(4) . . ? F2 C4 C3 121.9(5) . . ? C5 C4 C3 120.7(5) . . ? N1 C5 O1 121.1(5) . . ? N1 C5 C4 121.9(5) . . ? O1 C5 C4 117.0(5) . . ? O1 C6 C7 108.1(5) . . ? O2 C7 C6 107.9(5) . . ? O2 C8 C9 108.8(4) . . ? O3 C9 C8 111.8(5) . . ? N2 C10 O3 121.3(5) . . ? N2 C10 C11 121.1(5) . . ? O3 C10 C11 117.6(4) . . ? F10 C11 C10 117.0(4) . . ? F10 C11 C12 120.9(4) . . ? C10 C11 C12 121.9(5) . . ? C11 C12 C13 114.3(4) . . ? C11 C12 C22 123.1(4) . . ? C13 C12 C22 122.5(4) . . ? F11 C13 C14 117.6(5) . . ? F11 C13 C12 120.7(4) . . ? C14 C13 C12 121.6(5) . . ? N2 C14 O4 120.3(4) . . ? N2 C14 C13 122.3(5) . . ? O4 C14 C13 117.4(5) . . ? O4 C15 C16 108.5(4) . . ? O5 C16 C15 110.1(4) . . ? O5 C17 C18 108.9(4) . . ? O6 C18 C17 110.7(4) . . ? F3 C19 C3 108.6(4) . . ? F3 C19 C21 107.0(4) . . ? C3 C19 C21 111.1(4) . . ? F3 C19 C20 101.0(4) . . ? C3 C19 C20 117.1(5) . . ? C21 C19 C20 111.1(5) . . ? F5 C20 F4 107.6(5) . . ? F5 C20 F6 106.4(5) . . ? F4 C20 F6 107.5(5) . . ? F5 C20 C19 111.2(5) . . ? F4 C20 C19 111.5(5) . . ? F6 C20 C19 112.4(5) . . ? F7 C21 F9 108.1(4) . . ? F7 C21 F8 107.5(4) . . ? F9 C21 F8 107.6(4) . . ? F7 C21 C19 110.6(4) . . ? F9 C21 C19 109.6(4) . . ? F8 C21 C19 113.2(5) . . ? F12 C22 C23 105.7(4) . . ? F12 C22 C12 109.7(4) . . ? C23 C22 C12 110.0(4) . . ? F12 C22 C24 103.5(4) . . ? C23 C22 C24 111.3(4) . . ? C12 C22 C24 116.0(4) . . ? F14 C23 F13 109.3(5) . . ? F14 C23 F15 107.2(4) . . ? F13 C23 F15 105.6(4) . . ? F14 C23 C22 112.9(4) . . ? F13 C23 C22 111.9(4) . . ? F15 C23 C22 109.6(5) . . ? F18 C24 F16 109.6(5) . . ? F18 C24 F17 109.2(5) . . ? F16 C24 F17 106.4(5) . . ? F18 C24 C22 111.1(5) . . ? F16 C24 C22 109.3(5) . . ? F17 C24 C22 111.0(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 C5 N1 C1 O6 179.2(4) . . . . ? C5 N1 C1 C2 -2.3(7) . . . . ? C18 O6 C1 N1 -19.0(6) . . . . ? C18 O6 C1 C2 162.4(4) . . . . ? N1 C1 C2 F1 -180.0(4) . . . . ? O6 C1 C2 F1 -1.4(7) . . . . ? N1 C1 C2 C3 -0.4(8) . . . . ? O6 C1 C2 C3 178.2(4) . . . . ? F1 C2 C3 C4 -179.2(4) . . . . ? C1 C2 C3 C4 1.2(7) . . . . ? F1 C2 C3 C19 -1.7(8) . . . . ? C1 C2 C3 C19 178.7(5) . . . . ? C2 C3 C4 F2 178.4(5) . . . . ? C19 C3 C4 F2 0.7(7) . . . . ? C2 C3 C4 C5 0.4(7) . . . . ? C19 C3 C4 C5 -177.3(5) . . . . ? C1 N1 C5 O1 -175.7(5) . . . . ? C1 N1 C5 C4 4.0(7) . . . . ? C6 O1 C5 N1 -2.5(7) . . . . ? C6 O1 C5 C4 177.8(5) . . . . ? F2 C4 C5 N1 178.8(4) . . . . ? C3 C4 C5 N1 -3.1(8) . . . . ? F2 C4 C5 O1 -1.5(7) . . . . ? C3 C4 C5 O1 176.6(5) . . . . ? C5 O1 C6 C7 159.6(5) . . . . ? C8 O2 C7 C6 -172.8(5) . . . . ? O1 C6 C7 O2 -71.9(6) . . . . ? C7 O2 C8 C9 -175.7(5) . . . . ? C10 O3 C9 C8 -93.0(6) . . . . ? O2 C8 C9 O3 70.4(6) . . . . ? C14 N2 C10 O3 178.6(4) . . . . ? C14 N2 C10 C11 -1.3(7) . . . . ? C9 O3 C10 N2 -3.6(7) . . . . ? C9 O3 C10 C11 176.3(5) . . . . ? N2 C10 C11 F10 -177.4(4) . . . . ? O3 C10 C11 F10 2.6(7) . . . . ? N2 C10 C11 C12 -1.9(8) . . . . ? O3 C10 C11 C12 178.1(4) . . . . ? F10 C11 C12 C13 179.1(5) . . . . ? C10 C11 C12 C13 3.8(7) . . . . ? F10 C11 C12 C22 2.5(7) . . . . ? C10 C11 C12 C22 -172.8(5) . . . . ? C11 C12 C13 F11 -178.0(4) . . . . ? C22 C12 C13 F11 -1.4(8) . . . . ? C11 C12 C13 C14 -2.6(7) . . . . ? C22 C12 C13 C14 174.0(5) . . . . ? C10 N2 C14 O4 -177.4(4) . . . . ? C10 N2 C14 C13 2.5(7) . . . . ? C15 O4 C14 N2 -10.9(6) . . . . ? C15 O4 C14 C13 169.2(5) . . . . ? F11 C13 C14 N2 175.1(4) . . . . ? C12 C13 C14 N2 -0.4(8) . . . . ? F11 C13 C14 O4 -5.0(7) . . . . ? C12 C13 C14 O4 179.5(4) . . . . ? C14 O4 C15 C16 162.9(4) . . . . ? C17 O5 C16 C15 -169.6(4) . . . . ? O4 C15 C16 O5 -75.4(5) . . . . ? C16 O5 C17 C18 -178.3(4) . . . . ? C1 O6 C18 C17 -84.9(5) . . . . ? O5 C17 C18 O6 69.5(6) . . . . ? C2 C3 C19 F3 144.3(5) . . . . ? C4 C3 C19 F3 -38.3(6) . . . . ? C2 C3 C19 C21 -98.3(6) . . . . ? C4 C3 C19 C21 79.1(6) . . . . ? C2 C3 C19 C20 30.9(7) . . . . ? C4 C3 C19 C20 -151.7(5) . . . . ? F3 C19 C20 F5 42.7(6) . . . . ? C3 C19 C20 F5 160.3(4) . . . . ? C21 C19 C20 F5 -70.5(6) . . . . ? F3 C19 C20 F4 -77.4(5) . . . . ? C3 C19 C20 F4 40.2(6) . . . . ? C21 C19 C20 F4 169.4(4) . . . . ? F3 C19 C20 F6 161.8(4) . . . . ? C3 C19 C20 F6 -80.6(6) . . . . ? C21 C19 C20 F6 48.6(6) . . . . ? F3 C19 C21 F7 56.4(6) . . . . ? C3 C19 C21 F7 -62.0(6) . . . . ? C20 C19 C21 F7 165.7(4) . . . . ? F3 C19 C21 F9 175.6(4) . . . . ? C3 C19 C21 F9 57.2(6) . . . . ? C20 C19 C21 F9 -75.1(6) . . . . ? F3 C19 C21 F8 -64.3(6) . . . . ? C3 C19 C21 F8 177.3(4) . . . . ? C20 C19 C21 F8 45.0(6) . . . . ? C11 C12 C22 F12 -156.7(4) . . . . ? C13 C12 C22 F12 27.0(7) . . . . ? C11 C12 C22 C23 87.4(6) . . . . ? C13 C12 C22 C23 -88.9(6) . . . . ? C11 C12 C22 C24 -40.0(7) . . . . ? C13 C12 C22 C24 143.7(5) . . . . ? F12 C22 C23 F14 63.6(5) . . . . ? C12 C22 C23 F14 -178.0(4) . . . . ? C24 C22 C23 F14 -48.0(6) . . . . ? F12 C22 C23 F13 -172.6(4) . . . . ? C12 C22 C23 F13 -54.3(6) . . . . ? C24 C22 C23 F13 75.7(5) . . . . ? F12 C22 C23 F15 -55.8(5) . . . . ? C12 C22 C23 F15 62.5(5) . . . . ? C24 C22 C23 F15 -167.5(4) . . . . ? F12 C22 C24 F18 87.1(5) . . . . ? C23 C22 C24 F18 -159.8(5) . . . . ? C12 C22 C24 F18 -33.0(7) . . . . ? F12 C22 C24 F16 -34.1(6) . . . . ? C23 C22 C24 F16 79.1(6) . . . . ? C12 C22 C24 F16 -154.2(5) . . . . ? F12 C22 C24 F17 -151.2(4) . . . . ? C23 C22 C24 F17 -38.1(6) . . . . ? C12 C22 C24 F17 88.7(6) . . . . ? _diffrn_measured_fraction_theta_max 0.987 _diffrn_reflns_theta_full 27.50 _diffrn_measured_fraction_theta_full 0.987 _refine_diff_density_max 0.382 _refine_diff_density_min -0.427 _refine_diff_density_rms 0.097 data_s138 _database_code_CSD 197404 _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C24 H16 F18 N2 O6' _chemical_formula_weight 770.39 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/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 11.0542(4) _cell_length_b 14.1784(5) _cell_length_c 18.7552(6) _cell_angle_alpha 90.00 _cell_angle_beta 102.960(1) _cell_angle_gamma 90.00 _cell_volume 2864.64(17) _cell_formula_units_Z 4 _cell_measurement_temperature 120(2) _cell_measurement_reflns_used 5732 _cell_measurement_theta_min 2.4 _cell_measurement_theta_max 24.6 _exptl_crystal_description cube _exptl_crystal_colour colourless _exptl_crystal_size_max 0.36 _exptl_crystal_size_mid 0.32 _exptl_crystal_size_min 0.32 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.786 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1536 _exptl_absorpt_coefficient_mu 0.202 _exptl_absorpt_correction_type none _exptl_absorpt_correction_T_min 0.9308 _exptl_absorpt_correction_T_max 0.9382 _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 120(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 SMART CCD' _diffrn_measurement_method \w-scan _diffrn_detector_area_resol_mean 8 _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% 0 _diffrn_reflns_number 33009 _diffrn_reflns_av_R_equivalents 0.0287 _diffrn_reflns_av_sigmaI/netI 0.0182 _diffrn_reflns_limit_h_min -14 _diffrn_reflns_limit_h_max 14 _diffrn_reflns_limit_k_min -19 _diffrn_reflns_limit_k_max 19 _diffrn_reflns_limit_l_min -26 _diffrn_reflns_limit_l_max 26 _diffrn_reflns_theta_min 1.89 _diffrn_reflns_theta_max 30.20 _reflns_number_total 7801 _reflns_number_gt 6566 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SMART' _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^)+(0.0500P)^2^+2.0000P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens difmap _refine_ls_hydrogen_treatment refall _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 7801 _refine_ls_number_parameters 515 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0532 _refine_ls_R_factor_gt 0.0439 _refine_ls_wR_factor_ref 0.1175 _refine_ls_wR_factor_gt 0.1101 _refine_ls_goodness_of_fit_ref 1.053 _refine_ls_restrained_S_all 1.053 _refine_ls_shift/su_max 0.001 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group O1 O 0.48760(11) 0.76539(8) 0.74768(6) 0.0249(2) Uani 1 1 d . . . O2 O 0.35690(12) 0.89455(8) 0.64123(6) 0.0272(2) Uani 1 1 d . . . O3 O 0.53169(10) 1.02018(9) 0.59030(6) 0.0257(2) Uani 1 1 d . . . O4 O 0.53814(10) 1.04922(8) 0.83950(6) 0.0238(2) Uani 1 1 d . . . O5 O 0.36114(11) 0.94170(8) 0.89712(6) 0.0246(2) Uani 1 1 d . . . O6 O 0.44361(10) 0.77572(8) 0.98759(6) 0.0239(2) Uani 1 1 d . . . N1 N 0.46588(11) 0.76563(9) 0.86756(7) 0.0203(2) Uani 1 1 d . . . N2 N 0.53081(11) 1.03696(9) 0.71465(7) 0.0196(2) Uani 1 1 d . . . C1 C 0.51619(13) 0.76964(10) 0.93832(8) 0.0202(3) Uani 1 1 d . . . C2 C 0.64472(14) 0.76690(11) 0.96466(8) 0.0218(3) Uani 1 1 d . . . C3 C 0.72434(14) 0.76541(10) 0.91597(8) 0.0220(3) Uani 1 1 d . . . C4 C 0.66775(14) 0.76437(11) 0.84202(9) 0.0230(3) Uani 1 1 d . . . C5 C 0.53788(14) 0.76491(10) 0.82000(8) 0.0209(3) Uani 1 1 d . . . C6 C 0.35375(15) 0.77534(11) 0.72732(9) 0.0246(3) Uani 1 1 d . . . C7 C 0.32086(17) 0.79951(11) 0.64716(9) 0.0273(3) Uani 1 1 d . . . C8 C 0.34161(15) 0.92707(11) 0.56829(8) 0.0247(3) Uani 1 1 d . . . C9 C 0.39744(14) 1.02432(11) 0.57111(8) 0.0216(3) Uani 1 1 d . . . C10 C 0.59070(14) 1.02072(10) 0.66162(8) 0.0208(3) Uani 1 1 d . . . C11 C 0.71835(14) 1.00603(11) 0.67671(8) 0.0232(3) Uani 1 1 d . . . C12 C 0.78915(14) 1.00865(11) 0.74811(8) 0.0227(3) Uani 1 1 d . . . C13 C 0.72341(14) 1.02335(11) 0.80249(8) 0.0232(3) Uani 1 1 d . . . C14 C 0.59473(13) 1.03607(10) 0.78351(8) 0.0197(3) Uani 1 1 d . . . C15 C 0.40503(14) 1.06492(11) 0.82142(8) 0.0228(3) Uani 1 1 d . . . C16 C 0.35793(15) 1.04136(11) 0.88869(9) 0.0230(3) Uani 1 1 d . . . C17 C 0.30437(15) 0.91082(12) 0.95400(9) 0.0252(3) Uani 1 1 d . . . C18 C 0.31528(14) 0.80475(12) 0.95924(9) 0.0250(3) Uani 1 1 d . . . C19 C 0.86583(14) 0.76127(12) 0.94186(9) 0.0253(3) Uani 1 1 d . . . C20 C 0.90869(15) 0.65787(13) 0.95844(11) 0.0320(4) Uani 1 1 d . . . C21 C 0.92244(16) 0.82770(15) 1.00734(10) 0.0354(4) Uani 1 1 d . . . C22 C 0.93074(15) 1.00575(13) 0.76479(9) 0.0287(3) Uani 1 1 d . . . C23 C 0.97940(16) 1.10486(15) 0.74927(10) 0.0353(4) Uani 1 1 d . . . C24 C 0.98814(17) 0.92548(15) 0.72592(11) 0.0387(4) Uani 1 1 d . . . F1 F 0.69087(9) 0.76533(7) 1.03735(5) 0.0288(2) Uani 1 1 d . . . F2 F 0.73234(9) 0.76170(8) 0.78907(5) 0.0315(2) Uani 1 1 d . . . F3 F 0.92073(9) 0.79072(8) 0.88668(6) 0.0336(2) Uani 1 1 d . . . F4 F 0.87407(10) 0.60705(8) 0.89798(7) 0.0388(3) Uani 1 1 d . . . F5 F 0.85953(10) 0.61926(9) 1.01001(7) 0.0412(3) Uani 1 1 d . . . F6 F 1.03264(10) 0.65294(9) 0.98023(8) 0.0476(3) Uani 1 1 d . . . F7 F 0.92754(11) 0.78674(11) 1.07173(6) 0.0492(3) Uani 1 1 d . . . F8 F 1.03866(10) 0.85008(10) 1.00506(7) 0.0495(3) Uani 1 1 d . . . F9 F 0.85722(11) 0.90689(9) 1.00431(7) 0.0459(3) Uani 1 1 d . . . F10 F 0.77263(9) 0.99142(8) 0.61993(5) 0.0322(2) Uani 1 1 d . . . F11 F 0.77984(9) 1.02945(9) 0.87399(5) 0.0365(3) Uani 1 1 d . . . F12 F 0.97752(10) 0.99085(9) 0.83840(6) 0.0401(3) Uani 1 1 d . . . F13 F 0.94403(12) 1.16757(9) 0.79374(7) 0.0468(3) Uani 1 1 d . . . F14 F 0.93412(10) 1.13259(8) 0.68103(6) 0.0368(2) Uani 1 1 d . . . F15 F 1.10310(10) 1.10597(11) 0.76198(7) 0.0531(4) Uani 1 1 d . . . F16 F 1.00778(11) 0.95127(9) 0.66115(6) 0.0425(3) Uani 1 1 d . . . F17 F 0.91492(12) 0.85006(9) 0.71639(8) 0.0511(3) Uani 1 1 d . . . F18 F 1.09814(12) 0.90045(12) 0.76757(8) 0.0610(4) Uani 1 1 d . . . H61 H 0.3290(18) 0.8260(14) 0.7543(10) 0.023(5) Uiso 1 1 d . . . H62 H 0.319(2) 0.7170(16) 0.7368(11) 0.031(5) Uiso 1 1 d . . . H71 H 0.363(2) 0.7566(15) 0.6194(12) 0.032(5) Uiso 1 1 d . . . H72 H 0.231(2) 0.7907(15) 0.6296(11) 0.029(5) Uiso 1 1 d . . . H81 H 0.3824(19) 0.8862(15) 0.5394(11) 0.027(5) Uiso 1 1 d . . . H82 H 0.252(2) 0.9302(16) 0.5435(13) 0.040(6) Uiso 1 1 d . . . H91 H 0.3660(18) 1.0632(14) 0.6046(10) 0.022(4) Uiso 1 1 d . . . H92 H 0.3780(18) 1.0532(14) 0.5224(11) 0.023(5) Uiso 1 1 d . . . H151 H 0.366(2) 1.0249(15) 0.7820(12) 0.030(5) Uiso 1 1 d . . . H152 H 0.3877(19) 1.1291(16) 0.8077(11) 0.029(5) Uiso 1 1 d . . . H161 H 0.2732(18) 1.0648(13) 0.8835(10) 0.021(4) Uiso 1 1 d . . . H162 H 0.408(2) 1.0724(16) 0.9322(12) 0.034(5) Uiso 1 1 d . . . H171 H 0.3428(19) 0.9396(14) 0.9999(11) 0.026(5) Uiso 1 1 d . . . H172 H 0.2190(19) 0.9270(14) 0.9434(11) 0.024(5) Uiso 1 1 d . . . H181 H 0.2826(18) 0.7751(14) 0.9118(11) 0.025(5) Uiso 1 1 d . . . H182 H 0.2731(19) 0.7809(15) 0.9943(11) 0.029(5) Uiso 1 1 d . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 O1 0.0245(5) 0.0283(5) 0.0221(5) 0.0001(4) 0.0056(4) 0.0047(4) O2 0.0387(6) 0.0210(5) 0.0196(5) 0.0000(4) 0.0015(4) -0.0058(5) O3 0.0197(5) 0.0397(6) 0.0176(5) -0.0032(4) 0.0038(4) -0.0024(4) O4 0.0198(5) 0.0341(6) 0.0182(5) -0.0002(4) 0.0059(4) -0.0009(4) O5 0.0298(6) 0.0217(5) 0.0270(5) 0.0045(4) 0.0161(4) 0.0038(4) O6 0.0218(5) 0.0296(6) 0.0214(5) 0.0057(4) 0.0071(4) 0.0061(4) N1 0.0196(6) 0.0184(5) 0.0229(6) 0.0017(4) 0.0049(5) 0.0018(4) N2 0.0191(6) 0.0209(6) 0.0188(6) -0.0012(4) 0.0045(4) -0.0019(4) C1 0.0200(7) 0.0177(6) 0.0241(7) 0.0014(5) 0.0070(5) 0.0021(5) C2 0.0212(7) 0.0225(7) 0.0210(7) -0.0014(5) 0.0028(5) 0.0028(5) C3 0.0184(7) 0.0195(6) 0.0281(7) -0.0022(5) 0.0052(5) 0.0005(5) C4 0.0222(7) 0.0225(7) 0.0262(7) -0.0009(5) 0.0096(6) 0.0010(5) C5 0.0225(7) 0.0169(6) 0.0239(7) 0.0001(5) 0.0063(5) 0.0019(5) C6 0.0243(7) 0.0226(7) 0.0256(7) 0.0014(6) 0.0030(6) 0.0003(6) C7 0.0331(8) 0.0211(7) 0.0249(7) -0.0016(6) 0.0001(6) -0.0035(6) C8 0.0269(8) 0.0267(7) 0.0181(7) -0.0015(5) 0.0001(6) -0.0020(6) C9 0.0195(7) 0.0250(7) 0.0191(6) 0.0006(5) 0.0019(5) 0.0010(5) C10 0.0203(7) 0.0228(7) 0.0192(6) -0.0025(5) 0.0041(5) -0.0030(5) C11 0.0213(7) 0.0287(7) 0.0214(7) -0.0020(5) 0.0088(5) -0.0010(6) C12 0.0181(7) 0.0266(7) 0.0237(7) 0.0024(5) 0.0054(5) -0.0003(5) C13 0.0212(7) 0.0295(7) 0.0180(6) 0.0019(5) 0.0028(5) -0.0024(6) C14 0.0206(7) 0.0201(6) 0.0190(6) -0.0001(5) 0.0057(5) -0.0026(5) C15 0.0213(7) 0.0243(7) 0.0238(7) 0.0038(6) 0.0070(5) 0.0019(5) C16 0.0249(7) 0.0216(7) 0.0250(7) 0.0017(5) 0.0108(6) 0.0040(6) C17 0.0239(7) 0.0294(8) 0.0261(7) 0.0070(6) 0.0136(6) 0.0066(6) C18 0.0185(7) 0.0307(8) 0.0281(8) 0.0089(6) 0.0101(6) 0.0033(6) C19 0.0194(7) 0.0314(8) 0.0257(7) -0.0027(6) 0.0065(6) -0.0008(6) C20 0.0184(7) 0.0346(9) 0.0434(10) 0.0004(7) 0.0074(7) 0.0047(6) C21 0.0232(8) 0.0487(11) 0.0337(9) -0.0123(8) 0.0049(6) -0.0055(7) C22 0.0183(7) 0.0421(9) 0.0249(7) 0.0058(6) 0.0030(6) 0.0006(6) C23 0.0230(8) 0.0491(11) 0.0324(9) 0.0022(8) 0.0035(6) -0.0091(7) C24 0.0254(8) 0.0485(11) 0.0445(10) 0.0082(8) 0.0123(7) 0.0084(8) F1 0.0263(5) 0.0379(5) 0.0206(4) -0.0021(4) 0.0018(4) 0.0046(4) F2 0.0267(5) 0.0443(6) 0.0265(5) -0.0020(4) 0.0126(4) 0.0015(4) F3 0.0280(5) 0.0452(6) 0.0301(5) 0.0010(4) 0.0120(4) -0.0050(4) F4 0.0326(5) 0.0341(5) 0.0529(7) -0.0107(5) 0.0165(5) 0.0042(4) F5 0.0317(6) 0.0472(7) 0.0444(6) 0.0149(5) 0.0081(5) 0.0053(5) F6 0.0187(5) 0.0522(7) 0.0694(8) 0.0060(6) 0.0049(5) 0.0101(5) F7 0.0390(6) 0.0799(9) 0.0257(5) -0.0065(6) 0.0008(5) -0.0021(6) F8 0.0241(5) 0.0700(9) 0.0549(7) -0.0251(6) 0.0101(5) -0.0184(5) F9 0.0410(6) 0.0403(6) 0.0567(7) -0.0210(5) 0.0118(5) -0.0065(5) F10 0.0241(5) 0.0511(6) 0.0240(5) -0.0063(4) 0.0106(4) -0.0001(4) F11 0.0241(5) 0.0659(7) 0.0176(4) 0.0017(4) 0.0006(4) -0.0008(5) F12 0.0232(5) 0.0673(8) 0.0280(5) 0.0134(5) 0.0019(4) 0.0047(5) F13 0.0477(7) 0.0501(7) 0.0417(6) -0.0125(5) 0.0080(5) -0.0195(6) F14 0.0301(5) 0.0466(6) 0.0332(5) 0.0093(5) 0.0059(4) -0.0069(4) F15 0.0213(5) 0.0815(10) 0.0533(7) 0.0140(7) 0.0014(5) -0.0160(6) F16 0.0332(6) 0.0567(7) 0.0427(6) 0.0003(5) 0.0195(5) 0.0031(5) F17 0.0462(7) 0.0361(6) 0.0794(9) 0.0045(6) 0.0316(7) 0.0079(5) F18 0.0314(6) 0.0905(11) 0.0618(8) 0.0167(8) 0.0123(6) 0.0298(7) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag O1 C5 1.3456(18) . ? O1 C6 1.4497(19) . ? O2 C7 1.4165(19) . ? O2 C8 1.4173(19) . ? O3 C10 1.3503(18) . ? O3 C9 1.4476(18) . ? O4 C14 1.3504(17) . ? O4 C15 1.4511(18) . ? O5 C16 1.4215(18) . ? O5 C17 1.4225(17) . ? O6 C1 1.3555(17) . ? O6 C18 1.4581(18) . ? N1 C1 1.3202(19) . ? N1 C5 1.3219(19) . ? N2 C14 1.3259(19) . ? N2 C10 1.3326(18) . ? C1 C2 1.396(2) . ? C2 F1 1.3444(17) . ? C2 C3 1.403(2) . ? C3 C4 1.388(2) . ? C3 C19 1.531(2) . ? C4 F2 1.3473(17) . ? C4 C5 1.402(2) . ? C6 C7 1.505(2) . ? C8 C9 1.507(2) . ? C10 C11 1.391(2) . ? C11 F10 1.3504(16) . ? C11 C12 1.392(2) . ? C12 C13 1.394(2) . ? C12 C22 1.526(2) . ? C13 F11 1.3489(17) . ? C13 C14 1.398(2) . ? C15 C16 1.506(2) . ? C17 C18 1.510(2) . ? C19 F3 1.3768(18) . ? C19 C20 1.551(2) . ? C19 C21 1.563(2) . ? C20 F4 1.325(2) . ? C20 F5 1.329(2) . ? C20 F6 1.3409(19) . ? C21 F9 1.329(2) . ? C21 F7 1.330(2) . ? C21 F8 1.333(2) . ? C22 F12 1.3776(19) . ? C22 C23 1.555(3) . ? C22 C24 1.561(3) . ? C23 F14 1.325(2) . ? C23 F15 1.334(2) . ? C23 F13 1.336(2) . ? C24 F17 1.329(2) . ? C24 F16 1.332(2) . ? C24 F18 1.337(2) . ? 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 C5 O1 C6 115.63(12) . . ? C7 O2 C8 114.23(12) . . ? C10 O3 C9 119.12(11) . . ? C14 O4 C15 117.50(11) . . ? C16 O5 C17 112.65(11) . . ? C1 O6 C18 116.45(11) . . ? C1 N1 C5 119.80(13) . . ? C14 N2 C10 118.68(13) . . ? N1 C1 O6 120.51(13) . . ? N1 C1 C2 121.36(13) . . ? O6 C1 C2 118.13(13) . . ? F1 C2 C1 118.94(13) . . ? F1 C2 C3 120.58(13) . . ? C1 C2 C3 120.47(14) . . ? C4 C3 C2 116.27(14) . . ? C4 C3 C19 121.06(13) . . ? C2 C3 C19 122.63(14) . . ? F2 C4 C3 122.84(14) . . ? F2 C4 C5 117.39(14) . . ? C3 C4 C5 119.77(14) . . ? N1 C5 O1 120.33(13) . . ? N1 C5 C4 122.21(14) . . ? O1 C5 C4 117.45(13) . . ? O1 C6 C7 106.80(13) . . ? O2 C7 C6 106.61(13) . . ? O2 C8 C9 107.74(12) . . ? O3 C9 C8 111.14(13) . . ? N2 C10 O3 121.99(13) . . ? N2 C10 C11 121.67(13) . . ? O3 C10 C11 116.32(13) . . ? F10 C11 C12 120.62(13) . . ? F10 C11 C10 118.18(13) . . ? C12 C11 C10 121.18(13) . . ? C11 C12 C13 115.78(14) . . ? C11 C12 C22 121.74(13) . . ? C13 C12 C22 122.19(14) . . ? F11 C13 C12 122.42(14) . . ? F11 C13 C14 117.52(13) . . ? C12 C13 C14 120.02(13) . . ? N2 C14 O4 121.17(13) . . ? N2 C14 C13 122.59(13) . . ? O4 C14 C13 116.23(13) . . ? O4 C15 C16 107.05(12) . . ? O5 C16 C15 107.99(12) . . ? O5 C17 C18 108.24(12) . . ? O6 C18 C17 111.21(13) . . ? F3 C19 C3 109.94(13) . . ? F3 C19 C20 105.73(13) . . ? C3 C19 C20 110.13(13) . . ? F3 C19 C21 103.98(13) . . ? C3 C19 C21 115.26(13) . . ? C20 C19 C21 111.21(14) . . ? F4 C20 F5 108.18(15) . . ? F4 C20 F6 108.16(14) . . ? F5 C20 F6 108.27(15) . . ? F4 C20 C19 109.01(14) . . ? F5 C20 C19 112.27(14) . . ? F6 C20 C19 110.84(14) . . ? F9 C21 F7 108.66(15) . . ? F9 C21 F8 108.37(16) . . ? F7 C21 F8 106.74(15) . . ? F9 C21 C19 110.97(15) . . ? F7 C21 C19 112.24(16) . . ? F8 C21 C19 109.71(14) . . ? F12 C22 C12 110.29(13) . . ? F12 C22 C23 104.97(14) . . ? C12 C22 C23 108.61(14) . . ? F12 C22 C24 104.81(14) . . ? C12 C22 C24 115.43(15) . . ? C23 C22 C24 112.17(14) . . ? F14 C23 F15 108.60(15) . . ? F14 C23 F13 107.78(16) . . ? F15 C23 F13 108.20(15) . . ? F14 C23 C22 112.17(15) . . ? F15 C23 C22 111.16(16) . . ? F13 C23 C22 108.82(14) . . ? F17 C24 F16 108.49(18) . . ? F17 C24 F18 108.16(17) . . ? F16 C24 F18 107.01(15) . . ? F17 C24 C22 110.51(14) . . ? F16 C24 C22 113.09(16) . . ? F18 C24 C22 109.41(17) . . ? 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 C5 N1 C1 O6 176.33(13) . . . . ? C5 N1 C1 C2 -4.3(2) . . . . ? C18 O6 C1 N1 -17.2(2) . . . . ? C18 O6 C1 C2 163.35(13) . . . . ? N1 C1 C2 F1 -175.94(13) . . . . ? O6 C1 C2 F1 3.5(2) . . . . ? N1 C1 C2 C3 3.8(2) . . . . ? O6 C1 C2 C3 -176.78(13) . . . . ? F1 C2 C3 C4 178.14(13) . . . . ? C1 C2 C3 C4 -1.6(2) . . . . ? F1 C2 C3 C19 0.4(2) . . . . ? C1 C2 C3 C19 -179.29(14) . . . . ? C2 C3 C4 F2 -179.14(14) . . . . ? C19 C3 C4 F2 -1.4(2) . . . . ? C2 C3 C4 C5 0.0(2) . . . . ? C19 C3 C4 C5 177.78(14) . . . . ? C1 N1 C5 O1 -176.81(13) . . . . ? C1 N1 C5 C4 2.7(2) . . . . ? C6 O1 C5 N1 5.36(19) . . . . ? C6 O1 C5 C4 -174.15(13) . . . . ? F2 C4 C5 N1 178.68(13) . . . . ? C3 C4 C5 N1 -0.5(2) . . . . ? F2 C4 C5 O1 -1.8(2) . . . . ? C3 C4 C5 O1 178.95(13) . . . . ? C5 O1 C6 C7 165.54(12) . . . . ? C8 O2 C7 C6 175.22(13) . . . . ? O1 C6 C7 O2 -73.68(16) . . . . ? C7 O2 C8 C9 -173.46(13) . . . . ? C10 O3 C9 C8 -87.71(16) . . . . ? O2 C8 C9 O3 73.19(16) . . . . ? C14 N2 C10 O3 179.77(13) . . . . ? C14 N2 C10 C11 -2.1(2) . . . . ? C9 O3 C10 N2 -8.7(2) . . . . ? C9 O3 C10 C11 173.07(13) . . . . ? N2 C10 C11 F10 -179.02(13) . . . . ? O3 C10 C11 F10 -0.8(2) . . . . ? N2 C10 C11 C12 -0.6(2) . . . . ? O3 C10 C11 C12 177.59(14) . . . . ? F10 C11 C12 C13 -179.45(14) . . . . ? C10 C11 C12 C13 2.2(2) . . . . ? F10 C11 C12 C22 6.6(2) . . . . ? C10 C11 C12 C22 -171.74(15) . . . . ? C11 C12 C13 F11 -178.63(15) . . . . ? C22 C12 C13 F11 -4.7(2) . . . . ? C11 C12 C13 C14 -1.2(2) . . . . ? C22 C12 C13 C14 172.76(15) . . . . ? C10 N2 C14 O4 -177.95(13) . . . . ? C10 N2 C14 C13 3.2(2) . . . . ? C15 O4 C14 N2 -0.4(2) . . . . ? C15 O4 C14 C13 178.53(13) . . . . ? F11 C13 C14 N2 176.04(14) . . . . ? C12 C13 C14 N2 -1.6(2) . . . . ? F11 C13 C14 O4 -2.9(2) . . . . ? C12 C13 C14 O4 179.55(14) . . . . ? C14 O4 C15 C16 159.21(13) . . . . ? C17 O5 C16 C15 -172.80(13) . . . . ? O4 C15 C16 O5 -72.88(15) . . . . ? C16 O5 C17 C18 -178.83(13) . . . . ? C1 O6 C18 C17 -83.71(16) . . . . ? O5 C17 C18 O6 69.53(17) . . . . ? C4 C3 C19 F3 21.7(2) . . . . ? C2 C3 C19 F3 -160.70(14) . . . . ? C4 C3 C19 C20 -94.40(17) . . . . ? C2 C3 C19 C20 83.18(18) . . . . ? C4 C3 C19 C21 138.80(16) . . . . ? C2 C3 C19 C21 -43.6(2) . . . . ? F3 C19 C20 F4 -58.52(16) . . . . ? C3 C19 C20 F4 60.21(17) . . . . ? C21 C19 C20 F4 -170.76(13) . . . . ? F3 C19 C20 F5 -178.37(13) . . . . ? C3 C19 C20 F5 -59.64(18) . . . . ? C21 C19 C20 F5 69.39(18) . . . . ? F3 C19 C20 F6 60.41(18) . . . . ? C3 C19 C20 F6 179.14(14) . . . . ? C21 C19 C20 F6 -51.83(19) . . . . ? F3 C19 C21 F9 86.94(16) . . . . ? C3 C19 C21 F9 -33.5(2) . . . . ? C20 C19 C21 F9 -159.72(15) . . . . ? F3 C19 C21 F7 -151.27(14) . . . . ? C3 C19 C21 F7 88.32(18) . . . . ? C20 C19 C21 F7 -37.92(19) . . . . ? F3 C19 C21 F8 -32.8(2) . . . . ? C3 C19 C21 F8 -153.18(15) . . . . ? C20 C19 C21 F8 80.57(19) . . . . ? C11 C12 C22 F12 -168.41(15) . . . . ? C13 C12 C22 F12 18.0(2) . . . . ? C11 C12 C22 C23 77.07(19) . . . . ? C13 C12 C22 C23 -96.49(18) . . . . ? C11 C12 C22 C24 -49.9(2) . . . . ? C13 C12 C22 C24 136.56(16) . . . . ? F12 C22 C23 F14 -175.25(14) . . . . ? C12 C22 C23 F14 -57.29(19) . . . . ? C24 C22 C23 F14 71.50(19) . . . . ? F12 C22 C23 F15 62.95(18) . . . . ? C12 C22 C23 F15 -179.09(14) . . . . ? C24 C22 C23 F15 -50.3(2) . . . . ? F12 C22 C23 F13 -56.10(17) . . . . ? C12 C22 C23 F13 61.86(18) . . . . ? C24 C22 C23 F13 -169.35(15) . . . . ? F12 C22 C24 F17 90.14(18) . . . . ? C12 C22 C24 F17 -31.4(2) . . . . ? C23 C22 C24 F17 -156.52(15) . . . . ? F12 C22 C24 F16 -148.01(15) . . . . ? C12 C22 C24 F16 90.45(19) . . . . ? C23 C22 C24 F16 -34.7(2) . . . . ? F12 C22 C24 F18 -28.8(2) . . . . ? C12 C22 C24 F18 -150.37(15) . . . . ? C23 C22 C24 F18 84.50(19) . . . . ? _diffrn_measured_fraction_theta_max 0.916 _diffrn_reflns_theta_full 30.20 _diffrn_measured_fraction_theta_full 0.916 _refine_diff_density_max 0.674 _refine_diff_density_min -0.314 _refine_diff_density_rms 0.056 data_103s _database_code_CSD 197405 _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C30 H12 F18 N2 O4' _chemical_formula_weight 806.42 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 'C 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' _cell_length_a 13.473(3) _cell_length_b 23.261(5) _cell_length_c 11.079(2) _cell_angle_alpha 90.00 _cell_angle_beta 113.78(3) _cell_angle_gamma 90.00 _cell_volume 3177.2(11) _cell_formula_units_Z 4 _cell_measurement_temperature 120.0(2) _cell_measurement_reflns_used 7295 _cell_measurement_theta_min 2.2 _cell_measurement_theta_max 30 _exptl_crystal_description plate _exptl_crystal_colour colourless _exptl_crystal_size_max 0.46 _exptl_crystal_size_mid 0.40 _exptl_crystal_size_min 0.20 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.686 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1600 _exptl_absorpt_coefficient_mu 0.182 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.9208 _exptl_absorpt_correction_T_max 0.9644 _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 120.0(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 SMART CCD' _diffrn_measurement_method \w-scan _diffrn_detector_area_resol_mean 8 _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% 0 _diffrn_reflns_number 15431 _diffrn_reflns_av_R_equivalents 0.0281 _diffrn_reflns_av_sigmaI/netI 0.0263 _diffrn_reflns_limit_h_min -16 _diffrn_reflns_limit_h_max 16 _diffrn_reflns_limit_k_min -28 _diffrn_reflns_limit_k_max 28 _diffrn_reflns_limit_l_min -13 _diffrn_reflns_limit_l_max 13 _diffrn_reflns_theta_min 1.75 _diffrn_reflns_theta_max 25.50 _reflns_number_total 5778 _reflns_number_gt 4792 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SMART' _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. Terminal perfluoroisopropyl groups are severely disordered. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details ; calc [1.00000+0.00000exp(0.00(sin\q/\l)^2^)]/ [\s^2^(Fo^2^)+0.0000+24.0000*P+(0.1400P)^2^+0.0000sin\q/\l] where P = 1.00000Fo^2^ + 0.00000Fc^2^ ; _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _refine_ls_abs_structure_Flack 0.1(18) _refine_ls_number_reflns 5778 _refine_ls_number_parameters 408 _refine_ls_number_restraints 2 _refine_ls_R_factor_all 0.1322 _refine_ls_R_factor_gt 0.1168 _refine_ls_wR_factor_ref 0.3100 _refine_ls_wR_factor_gt 0.2795 _refine_ls_goodness_of_fit_ref 1.095 _refine_ls_restrained_S_all 1.095 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group O1 O 0.8676(4) 0.8924(2) 0.4069(5) 0.0419(12) Uani 1 1 d . . . O2 O 1.0025(6) 0.7507(2) 0.1959(7) 0.0571(16) Uani 1 1 d . . . O3 O 1.1385(5) 0.8909(3) 0.0061(6) 0.0525(15) Uani 1 1 d . . . O4 O 0.9668(5) 1.0316(3) 0.1763(6) 0.0496(14) Uani 1 1 d . . . N1 N 0.9165(5) 0.9628(3) 0.2904(6) 0.0354(13) Uani 1 1 d . . . N2 N 1.0697(6) 0.8216(3) 0.1005(6) 0.0458(16) Uani 1 1 d . . . C1 C 0.9541(6) 0.8590(3) 0.4038(7) 0.0395(16) Uani 1 1 d . . . C2 C 1.0543(7) 0.8662(3) 0.4992(8) 0.0467(19) Uani 1 1 d . . . H2A H 1.0651 0.8937 0.5667 0.056 Uiso 1 1 calc R . . C3 C 1.1430(7) 0.8341(4) 0.5011(9) 0.050(2) Uani 1 1 d . . . C4 C 1.1217(8) 0.7964(4) 0.3959(9) 0.054(2) Uani 1 1 d . . . H4A H 1.1795 0.7745 0.3910 0.064 Uiso 1 1 calc R . . C5 C 1.0187(8) 0.7902(3) 0.2986(8) 0.049(2) Uani 1 1 d . . . C6 C 0.9339(8) 0.8207(3) 0.2997(8) 0.0464(19) Uani 1 1 d . . . H6A H 0.8632 0.8163 0.2322 0.056 Uiso 1 1 calc R . . C7 C 1.2584(9) 0.8416(5) 0.6116(14) 0.077(3) Uani 1 1 d . . . H7A H 1.2560 0.8698 0.6761 0.116 Uiso 1 1 calc R . . H7B H 1.3079 0.8551 0.5728 0.116 Uiso 1 1 calc R . . H7C H 1.2840 0.8047 0.6555 0.116 Uiso 1 1 calc R . . C8 C 1.0254(7) 0.7683(4) 0.0959(10) 0.050(2) Uani 1 1 d . . . C9 C 1.0063(8) 0.7340(4) -0.0107(9) 0.060(2) Uani 1 1 d . . . C10 C 1.0310(9) 0.7489(5) -0.1185(10) 0.067(3) Uani 1 1 d . B . C11 C 1.0736(9) 0.8023(5) -0.1077(8) 0.059(2) Uani 1 1 d . . . C12 C 1.0927(7) 0.8378(4) -0.0006(8) 0.048(2) Uani 1 1 d . . . C13 C 1.1393(7) 0.9291(4) 0.1042(8) 0.0431(18) Uani 1 1 d . . . C14 C 1.2396(7) 0.9392(5) 0.2091(9) 0.058(2) Uani 1 1 d . . . H14A H 1.3022 0.9188 0.2142 0.070 Uiso 1 1 calc R . . C15 C 1.2474(7) 0.9796(5) 0.3070(10) 0.059(2) Uani 1 1 d . . . C16 C 1.1542(7) 1.0100(4) 0.2943(9) 0.0498(19) Uani 1 1 d . . . H16A H 1.1581 1.0387 0.3571 0.060 Uiso 1 1 calc R . . C17 C 1.0568(6) 0.9984(3) 0.1909(8) 0.0410(17) Uani 1 1 d . . . C18 C 1.0468(6) 0.9580(3) 0.0943(7) 0.0386(16) Uani 1 1 d . . . H18A H 0.9788 0.9506 0.0238 0.046 Uiso 1 1 calc R . . C19 C 1.3524(16) 0.9908(10) 0.4211(19) 0.145(8) Uani 1 1 d . . . H19A H 1.3419 1.0203 0.4779 0.217 Uiso 1 1 calc R . . H19B H 1.4062 1.0041 0.3887 0.217 Uiso 1 1 calc R . . H19C H 1.3780 0.9552 0.4717 0.217 Uiso 1 1 calc R . . C20 C 0.9034(6) 1.0135(3) 0.2397(7) 0.0384(16) Uani 1 1 d . . . C21 C 0.8283(7) 1.0529(4) 0.2476(8) 0.0450(18) Uani 1 1 d . . . C22 C 0.7638(6) 1.0380(4) 0.3116(8) 0.0451(19) Uani 1 1 d . A . C23 C 0.7778(6) 0.9823(3) 0.3650(8) 0.0398(17) Uani 1 1 d . . . C24 C 0.8560(6) 0.9457(3) 0.3530(7) 0.0372(15) Uani 1 1 d . . . C25 C 0.6777(9) 1.0785(5) 0.3232(11) 0.065(2) Uiso 1 1 d . . . C26 C 0.5790(18) 1.0502(9) 0.318(2) 0.065(5) Uiso 0.50 1 d P A 1 F6 F 0.5840(11) 1.0428(6) 0.4342(14) 0.078(3) Uiso 0.50 1 d P A 1 C26' C 0.573(2) 1.0673(11) 0.230(3) 0.077(6) Uiso 0.50 1 d P A 2 F6' F 0.5836(10) 1.0773(6) 0.1096(13) 0.073(3) Uiso 0.50 1 d P A 2 C27 C 0.7286(15) 1.1189(8) 0.441(2) 0.050(4) Uiso 0.50 1 d P A 3 F9 F 0.7717(9) 1.0898(5) 0.5411(11) 0.061(3) Uiso 0.50 1 d P A 3 C27' C 0.7133(17) 1.1347(9) 0.374(2) 0.059(4) Uiso 0.50 1 d P A 4 F9' F 0.6916(12) 1.1662(6) 0.2615(15) 0.088(4) Uiso 0.50 1 d P A 4 C28 C 1.0132(11) 0.7108(6) -0.2368(14) 0.083(3) Uiso 1 1 d . . . C29 C 0.9042(10) 0.7197(5) -0.3448(12) 0.076(3) Uiso 1 1 d . B . C30 C 1.0935(16) 0.6932(9) -0.277(2) 0.056(4) Uiso 0.50 1 d P B 5 F16 F 1.0773(12) 0.6412(6) -0.3303(14) 0.067(3) Uiso 0.50 1 d P B 5 F17 F 1.1877(11) 0.7024(6) -0.1781(14) 0.078(3) Uiso 0.50 1 d P B 5 F18 F 1.0795(14) 0.7328(7) -0.373(2) 0.095(4) Uiso 0.50 1 d P B 5 C30' C 1.0689(11) 0.6543(6) -0.2045(13) 0.031(3) Uiso 0.50 1 d P B 6 F16' F 1.1146(10) 0.6335(5) -0.2824(12) 0.053(3) Uiso 0.50 1 d P B 6 F17' F 1.1551(8) 0.6535(4) -0.0824(10) 0.051(2) Uiso 0.50 1 d P B 6 F18' F 0.9977(10) 0.6207(6) -0.1936(12) 0.061(3) Uiso 0.50 1 d P B 6 F12 F 0.9740(11) 0.6477(6) -0.2041(13) 0.072(3) Uiso 0.50 1 d P B 7 F12' F 1.0993(11) 0.7381(6) -0.2984(15) 0.073(3) Uiso 0.50 1 d P B 8 F1 F 0.8231(4) 1.1061(2) 0.1969(5) 0.0544(12) Uiso 1 1 d . . . F2 F 0.7197(4) 0.9621(2) 0.4312(5) 0.0545(12) Uiso 1 1 d . . . F3 F 0.6373(11) 1.1170(6) 0.1958(14) 0.077(3) Uiso 0.50 1 d P A 9 F3' F 0.6761(11) 1.0555(6) 0.4645(14) 0.077(3) Uiso 0.50 1 d P A 10 F4 F 0.4975(9) 1.0995(5) 0.2507(11) 0.128(3) Uiso 1 1 d . . . F5 F 0.5402(7) 1.0128(4) 0.2319(9) 0.097(2) Uiso 1 1 d . . . F7 F 0.6609(6) 1.1580(3) 0.4488(7) 0.0816(18) Uiso 1 1 d . . . F8 F 0.8135(6) 1.1477(3) 0.4349(8) 0.091(2) Uiso 1 1 d . . . F10 F 1.1029(6) 0.8252(3) -0.2037(7) 0.0781(17) Uiso 1 1 d . . . F11 F 0.9619(6) 0.6802(3) -0.0077(7) 0.0812(18) Uiso 1 1 d . . . F13 F 0.8294(7) 0.7093(4) -0.2963(9) 0.108(3) Uiso 1 1 d . . . F14 F 0.8832(7) 0.6853(4) -0.4469(9) 0.104(2) Uiso 1 1 d . . . F15 F 0.8919(6) 0.7744(3) -0.3864(8) 0.0865(19) Uiso 1 1 d . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 O1 0.045(3) 0.039(3) 0.047(3) 0.008(2) 0.024(2) 0.004(2) O2 0.090(5) 0.037(3) 0.061(4) -0.004(3) 0.047(4) -0.002(3) O3 0.074(4) 0.057(4) 0.041(3) 0.005(3) 0.038(3) 0.011(3) O4 0.055(3) 0.053(3) 0.053(3) 0.018(3) 0.035(3) 0.015(3) N1 0.046(3) 0.036(3) 0.032(3) -0.003(2) 0.023(3) 0.002(2) N2 0.070(4) 0.047(4) 0.031(3) -0.005(3) 0.031(3) 0.005(3) C1 0.040(4) 0.047(4) 0.035(4) 0.007(3) 0.019(3) -0.003(3) C2 0.071(6) 0.041(4) 0.037(4) 0.000(3) 0.031(4) 0.002(4) C3 0.044(4) 0.057(5) 0.047(5) 0.010(4) 0.015(4) 0.004(4) C4 0.082(7) 0.043(4) 0.055(5) 0.010(4) 0.046(5) 0.000(4) C5 0.076(6) 0.034(4) 0.042(4) 0.002(3) 0.029(4) -0.002(4) C6 0.067(5) 0.040(4) 0.033(4) 0.001(3) 0.021(4) -0.016(4) C7 0.055(6) 0.081(7) 0.091(8) 0.001(6) 0.024(6) 0.006(5) C8 0.058(5) 0.039(4) 0.060(5) -0.005(4) 0.029(4) 0.010(4) C9 0.063(6) 0.058(6) 0.048(5) -0.014(4) 0.012(4) 0.012(4) C10 0.065(6) 0.066(6) 0.051(5) -0.011(5) 0.003(5) 0.035(5) C11 0.082(6) 0.076(6) 0.024(4) 0.002(4) 0.028(4) 0.024(5) C12 0.059(5) 0.052(5) 0.032(4) 0.002(3) 0.016(4) 0.017(4) C13 0.048(5) 0.053(5) 0.038(4) 0.002(3) 0.027(4) -0.003(4) C14 0.046(5) 0.087(7) 0.052(5) 0.004(5) 0.031(4) 0.012(4) C15 0.038(5) 0.077(6) 0.063(6) 0.008(5) 0.020(4) 0.006(4) C16 0.047(5) 0.057(5) 0.045(5) -0.008(4) 0.018(4) -0.004(4) C17 0.043(4) 0.046(4) 0.047(4) 0.010(3) 0.032(4) 0.005(3) C18 0.041(4) 0.045(4) 0.031(3) 0.009(3) 0.017(3) 0.001(3) C19 0.113(14) 0.174(18) 0.102(13) -0.038(13) -0.003(11) -0.033(13) C20 0.032(4) 0.046(4) 0.038(4) 0.001(3) 0.016(3) 0.010(3) C21 0.054(5) 0.043(4) 0.037(4) 0.002(3) 0.018(4) 0.011(4) C22 0.033(4) 0.060(5) 0.037(4) -0.017(4) 0.009(3) 0.001(3) C23 0.027(4) 0.053(4) 0.046(4) -0.007(3) 0.021(3) -0.006(3) C24 0.031(4) 0.043(4) 0.037(4) 0.000(3) 0.014(3) -0.002(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 O1 C24 1.358(9) . ? O1 C1 1.414(10) . ? O2 C8 1.329(11) . ? O2 C5 1.409(10) . ? O3 C12 1.368(11) . ? O3 C13 1.400(9) . ? O4 C20 1.374(9) . ? O4 C17 1.392(9) . ? N1 C20 1.287(10) . ? N1 C24 1.326(9) . ? N2 C12 1.331(11) . ? N2 C8 1.369(11) . ? C1 C2 1.348(12) . ? C1 C6 1.394(11) . ? C2 C3 1.402(12) . ? C3 C4 1.393(13) . ? C3 C7 1.552(15) . ? C4 C5 1.379(14) . ? C5 C6 1.349(13) . ? C8 C9 1.361(12) . ? C9 F11 1.392(13) . ? C9 C10 1.406(16) . ? C10 C11 1.355(16) . ? C10 C28 1.518(17) . ? C11 F10 1.382(12) . ? C11 C12 1.383(12) . ? C13 C18 1.380(11) . ? C13 C14 1.403(13) . ? C14 C15 1.406(14) . ? C15 C16 1.397(12) . ? C15 C19 1.491(19) . ? C16 C17 1.377(12) . ? C17 C18 1.389(11) . ? C20 C21 1.394(10) . ? C21 F1 1.348(10) . ? C21 C22 1.370(12) . ? C22 C23 1.405(12) . ? C22 C25 1.540(14) . ? C23 F2 1.355(9) . ? C23 C24 1.401(10) . ? C25 C26' 1.40(3) . ? C25 C27' 1.43(2) . ? C25 C26 1.47(2) . ? C25 C27 1.53(2) . ? C25 F3 1.572(17) . ? C25 F3' 1.663(18) . ? C26 F5 1.24(2) . ? C26 F6 1.27(3) . ? C26 F4 1.55(2) . ? C26' F5 1.35(3) . ? C26' F4 1.35(3) . ? C26' F6' 1.42(3) . ? C27 F9 1.23(2) . ? C27 F7 1.315(19) . ? C27 F8 1.35(2) . ? C27' F8 1.28(2) . ? C27' F9' 1.37(3) . ? C27' F7 1.40(2) . ? C28 C30 1.39(2) . ? C28 C30' 1.485(19) . ? C28 C29 1.488(18) . ? C28 F12 1.649(19) . ? C28 F12' 1.689(19) . ? C29 F14 1.319(15) . ? C29 F15 1.340(14) . ? C29 F13 1.341(14) . ? C30 F17 1.32(2) . ? C30 F16 1.33(2) . ? C30 F18 1.36(3) . ? C30' F18' 1.279(17) . ? C30' F16' 1.337(18) . ? C30' F17' 1.383(17) . ? 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 C24 O1 C1 116.2(6) . . ? C8 O2 C5 117.4(6) . . ? C12 O3 C13 118.5(6) . . ? C20 O4 C17 117.5(6) . . ? C20 N1 C24 119.7(6) . . ? C12 N2 C8 118.1(7) . . ? C2 C1 C6 121.9(8) . . ? C2 C1 O1 119.1(7) . . ? C6 C1 O1 118.9(7) . . ? C1 C2 C3 121.5(8) . . ? C4 C3 C2 115.9(8) . . ? C4 C3 C7 122.2(9) . . ? C2 C3 C7 121.9(9) . . ? C5 C4 C3 121.5(8) . . ? C6 C5 C4 121.8(8) . . ? C6 C5 O2 119.6(8) . . ? C4 C5 O2 118.7(8) . . ? C5 C6 C1 117.4(8) . . ? O2 C8 C9 121.1(8) . . ? O2 C8 N2 119.5(8) . . ? C9 C8 N2 119.5(9) . . ? C8 C9 F11 116.1(9) . . ? C8 C9 C10 124.4(10) . . ? F11 C9 C10 119.5(8) . . ? C11 C10 C9 112.9(8) . . ? C11 C10 C28 121.6(11) . . ? C9 C10 C28 125.5(11) . . ? C10 C11 F10 121.9(8) . . ? C10 C11 C12 123.3(9) . . ? F10 C11 C12 114.7(9) . . ? N2 C12 O3 117.5(7) . . ? N2 C12 C11 121.8(9) . . ? O3 C12 C11 120.6(8) . . ? C18 C13 O3 121.6(7) . . ? C18 C13 C14 121.4(8) . . ? O3 C13 C14 117.0(7) . . ? C13 C14 C15 119.9(8) . . ? C16 C15 C14 118.4(9) . . ? C16 C15 C19 120.2(12) . . ? C14 C15 C19 121.3(12) . . ? C17 C16 C15 120.0(8) . . ? C16 C17 C18 122.5(7) . . ? C16 C17 O4 118.8(8) . . ? C18 C17 O4 118.5(7) . . ? C13 C18 C17 117.7(7) . . ? N1 C20 O4 120.0(6) . . ? N1 C20 C21 123.5(7) . . ? O4 C20 C21 116.5(7) . . ? F1 C21 C22 120.7(7) . . ? F1 C21 C20 119.7(7) . . ? C22 C21 C20 119.5(8) . . ? C21 C22 C23 116.5(7) . . ? C21 C22 C25 123.0(8) . . ? C23 C22 C25 120.5(8) . . ? F2 C23 C24 117.5(7) . . ? F2 C23 C22 122.6(6) . . ? C24 C23 C22 119.9(6) . . ? N1 C24 O1 121.1(6) . . ? N1 C24 C23 120.8(7) . . ? O1 C24 C23 118.0(6) . . ? C26' C25 C27' 122.7(16) . . ? C26' C25 C26 42.0(13) . . ? C27' C25 C26 125.7(14) . . ? C26' C25 C27 135.9(15) . . ? C27' C25 C27 30.4(9) . . ? C26 C25 C27 113.4(13) . . ? C26' C25 C22 113.3(13) . . ? C27' C25 C22 116.6(11) . . ? C26 C25 C22 115.1(12) . . ? C27 C25 C22 110.7(10) . . ? C26' C25 F3 64.0(13) . . ? C27' C25 F3 76.8(12) . . ? C26 C25 F3 103.9(13) . . ? C27 C25 F3 106.9(11) . . ? C22 C25 F3 105.9(9) . . ? C26' C25 F3' 104.0(14) . . ? C27' C25 F3' 93.2(12) . . ? C26 C25 F3' 62.2(11) . . ? C27 C25 F3' 64.3(10) . . ? C22 C25 F3' 100.2(8) . . ? F3 C25 F3' 153.8(10) . . ? F5 C26 F6 121.1(19) . . ? F5 C26 C25 116.1(17) . . ? F6 C26 C25 110.2(18) . . ? F5 C26 F4 98.6(15) . . ? F6 C26 F4 109.0(16) . . ? C25 C26 F4 98.1(14) . . ? F5 C26' F4 104.2(18) . . ? F5 C26' C25 113.8(19) . . ? F4 C26' C25 112.1(19) . . ? F5 C26' F6' 109.1(19) . . ? F4 C26' F6' 116(2) . . ? C25 C26' F6' 102.0(18) . . ? F9 C27 F7 114.1(16) . . ? F9 C27 F8 102.5(15) . . ? F7 C27 F8 106.5(13) . . ? F9 C27 C25 108.6(14) . . ? F7 C27 C25 113.4(14) . . ? F8 C27 C25 111.2(14) . . ? F8 C27' F9' 98.5(16) . . ? F8 C27' F7 105.7(15) . . ? F9' C27' F7 111.0(16) . . ? F8 C27' C25 122.8(16) . . ? F9' C27' C25 102.7(16) . . ? F7 C27' C25 114.7(15) . . ? C30 C28 C30' 55.3(11) . . ? C30 C28 C29 115.3(14) . . ? C30' C28 C29 123.7(12) . . ? C30 C28 C10 125.2(14) . . ? C30' C28 C10 114.8(11) . . ? C29 C28 C10 112.0(11) . . ? C30 C28 F12 99.6(12) . . ? C30' C28 F12 48.2(8) . . ? C29 C28 F12 90.0(10) . . ? C10 C28 F12 106.4(11) . . ? C30 C28 F12' 39.7(9) . . ? C30' C28 F12' 93.9(10) . . ? C29 C28 F12' 103.8(11) . . ? C10 C28 F12' 103.6(10) . . ? F12 C28 F12' 139.1(11) . . ? F14 C29 F15 109.1(10) . . ? F14 C29 F13 107.3(10) . . ? F15 C29 F13 107.5(10) . . ? F14 C29 C28 114.0(11) . . ? F15 C29 C28 110.7(10) . . ? F13 C29 C28 108.1(11) . . ? F17 C30 F16 116.7(17) . . ? F17 C30 F18 108.9(17) . . ? F16 C30 F18 108.7(17) . . ? F17 C30 C28 107.5(16) . . ? F16 C30 C28 113.8(16) . . ? F18 C30 C28 99.8(16) . . ? F18' C30' F16' 113.5(12) . . ? F18' C30' F17' 105.4(11) . . ? F16' C30' F17' 101.7(11) . . ? F18' C30' C28 103.8(12) . . ? F16' C30' C28 118.9(12) . . ? F17' C30' C28 113.1(11) . . ? C26' F4 C26 40.6(13) . . ? C26 F5 C26' 46.5(14) . . ? C27 F7 C27' 33.2(10) . . ? C27' F8 C27 34.3(10) . . ? _diffrn_measured_fraction_theta_max 1.000 _diffrn_reflns_theta_full 25.50 _diffrn_measured_fraction_theta_full 1.000 _refine_diff_density_max 0.745 _refine_diff_density_min -0.645 _refine_diff_density_rms 0.109 data_s139 _database_code_CSD 208079 _audit_creation_method SHELXL-97 _chemical_name_systematic ; 19,20-diaza-8,17-bis[1,2,2,2-tetrafluoromethyl)ethyl] -7,9,16,18-tetrafluoro-2,5,11,14- tetraoxatricyclo[13.3.1.1<6,10>]icosa- 1(19),6,8,10(20),15,17-hexaene ; _chemical_name_common ? _chemical_melting_point 191-194 _chemical_formula_moiety ? _chemical_formula_sum 'C20 H8 F18 N2 O4' _chemical_formula_weight 682.28 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 'P 21/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 14.2011(5) _cell_length_b 8.4725(3) _cell_length_c 9.4479(3) _cell_angle_alpha 90.00 _cell_angle_beta 102.114(1) _cell_angle_gamma 90.00 _cell_volume 1111.45(7) _cell_formula_units_Z 2 _cell_measurement_temperature 120.0(2) _cell_measurement_reflns_used 4496 _cell_measurement_theta_min 2.8 _cell_measurement_theta_max 29.8 _exptl_crystal_description plate _exptl_crystal_colour colourless _exptl_crystal_size_max 0.32 _exptl_crystal_size_mid 0.26 _exptl_crystal_size_min 0.06 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 2.039 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 672 _exptl_absorpt_coefficient_mu 0.240 _exptl_absorpt_correction_type none _exptl_absorpt_correction_T_min 0.9273 _exptl_absorpt_correction_T_max 0.9858 _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 120.0(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 SMART CCD 1K' _diffrn_measurement_method /w-scan _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% 0 _diffrn_reflns_number 12347 _diffrn_reflns_av_R_equivalents 0.0516 _diffrn_reflns_av_sigmaI/netI 0.0391 _diffrn_reflns_limit_h_min -19 _diffrn_reflns_limit_h_max 19 _diffrn_reflns_limit_k_min -11 _diffrn_reflns_limit_k_max 11 _diffrn_reflns_limit_l_min -13 _diffrn_reflns_limit_l_max 12 _diffrn_reflns_theta_min 1.47 _diffrn_reflns_theta_max 30.31 _reflns_number_total 3089 _reflns_number_gt 2323 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SMART' _computing_data_reduction 'Bruker SHELXTL' _computing_structure_solution 'SHELXS (Sheldrick, 1990)' _computing_structure_refinement 'SHELX-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^)+(0.0500P)^2^+0.6000P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens difmap _refine_ls_hydrogen_treatment refall _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 3089 _refine_ls_number_parameters 215 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0643 _refine_ls_R_factor_gt 0.0429 _refine_ls_wR_factor_ref 0.1101 _refine_ls_wR_factor_gt 0.0997 _refine_ls_goodness_of_fit_ref 1.022 _refine_ls_restrained_S_all 1.022 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group O1 O 0.51872(9) 0.13881(15) 0.29736(14) 0.0197(3) Uani 1 1 d . . . O2 O 0.29223(9) 0.00787(16) -0.11802(13) 0.0201(3) Uani 1 1 d . . . N1 N 0.40769(11) 0.06509(17) 0.09001(16) 0.0168(3) Uani 1 1 d . . . C1 C 0.42879(12) 0.09422(19) 0.23045(18) 0.0155(3) Uani 1 1 d . . . C2 C 0.35994(12) 0.0861(2) 0.31611(18) 0.0164(3) Uani 1 1 d . . . C3 C 0.26340(12) 0.05577(19) 0.25212(18) 0.0161(3) Uani 1 1 d . . . C4 C 0.24413(12) 0.0264(2) 0.10363(19) 0.0178(3) Uani 1 1 d . . . C5 C 0.31743(12) 0.0324(2) 0.02638(19) 0.0166(3) Uani 1 1 d . . . C6 C 0.36758(13) 0.0154(2) -0.1991(2) 0.0185(4) Uani 1 1 d . . . C7 C 0.58996(12) 0.1479(2) 0.2079(2) 0.0181(3) Uani 1 1 d . . . C8 C 0.18606(13) 0.0516(2) 0.34206(19) 0.0178(3) Uani 1 1 d . . . C9 C 0.17167(13) -0.1189(2) 0.3917(2) 0.0218(4) Uani 1 1 d . . . C10 C 0.08771(13) 0.1305(2) 0.2694(2) 0.0232(4) Uani 1 1 d . . . F1 F 0.38989(7) 0.10973(13) 0.45937(11) 0.0221(2) Uani 1 1 d . . . F2 F 0.15446(7) -0.00653(14) 0.03138(12) 0.0238(2) Uani 1 1 d . . . F3 F 0.21673(8) 0.13771(13) 0.46709(11) 0.0223(2) Uani 1 1 d . . . F4 F 0.25331(8) -0.16754(13) 0.47931(12) 0.0278(3) Uani 1 1 d . . . F5 F 0.15175(9) -0.21708(13) 0.27968(13) 0.0285(3) Uani 1 1 d . . . F6 F 0.10178(9) -0.12737(15) 0.46524(14) 0.0350(3) Uani 1 1 d . . . F7 F 0.02822(8) 0.03105(16) 0.18697(13) 0.0311(3) Uani 1 1 d . . . F8 F 0.10340(9) 0.25387(14) 0.19011(13) 0.0313(3) Uani 1 1 d . . . F9 F 0.04452(8) 0.18250(16) 0.37266(13) 0.0326(3) Uani 1 1 d . . . H71 H 0.6386(15) 0.216(2) 0.258(2) 0.012(5) Uiso 1 1 d . . . H72 H 0.5601(14) 0.187(2) 0.115(2) 0.013(5) Uiso 1 1 d . . . H61 H 0.3348(17) 0.048(3) -0.293(3) 0.028(6) Uiso 1 1 d . . . H62 H 0.4180(16) 0.087(3) -0.155(2) 0.024(6) Uiso 1 1 d . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 O1 0.0163(6) 0.0250(7) 0.0184(6) -0.0057(5) 0.0049(5) -0.0030(5) O2 0.0165(6) 0.0302(7) 0.0141(6) -0.0025(5) 0.0041(5) 0.0013(5) N1 0.0176(7) 0.0152(7) 0.0178(7) -0.0010(6) 0.0041(6) 0.0001(5) C1 0.0174(8) 0.0129(7) 0.0167(8) -0.0014(6) 0.0046(6) 0.0001(6) C2 0.0185(8) 0.0166(8) 0.0143(8) -0.0007(6) 0.0037(6) 0.0000(6) C3 0.0193(8) 0.0133(7) 0.0170(8) 0.0012(6) 0.0068(6) 0.0007(6) C4 0.0162(8) 0.0177(8) 0.0193(8) -0.0008(7) 0.0031(6) 0.0004(6) C5 0.0187(8) 0.0166(8) 0.0151(8) 0.0001(6) 0.0048(6) 0.0013(6) C6 0.0191(8) 0.0225(9) 0.0147(8) 0.0006(7) 0.0054(7) -0.0001(7) C7 0.0154(8) 0.0209(8) 0.0184(9) -0.0024(7) 0.0048(7) -0.0032(6) C8 0.0184(8) 0.0196(8) 0.0158(8) -0.0016(7) 0.0043(6) -0.0003(6) C9 0.0215(9) 0.0232(9) 0.0214(9) 0.0028(7) 0.0063(7) -0.0019(7) C10 0.0211(9) 0.0289(10) 0.0209(9) 0.0015(8) 0.0074(7) 0.0057(7) F1 0.0208(5) 0.0312(6) 0.0145(5) -0.0036(4) 0.0039(4) -0.0016(4) F2 0.0163(5) 0.0341(6) 0.0203(5) -0.0050(5) 0.0025(4) -0.0025(4) F3 0.0231(5) 0.0264(6) 0.0186(5) -0.0059(4) 0.0068(4) 0.0000(4) F4 0.0300(6) 0.0249(6) 0.0262(6) 0.0069(5) 0.0008(5) 0.0013(5) F5 0.0329(6) 0.0226(6) 0.0285(6) -0.0024(5) 0.0029(5) -0.0070(5) F6 0.0323(6) 0.0387(7) 0.0400(7) 0.0104(6) 0.0209(6) -0.0039(5) F7 0.0169(5) 0.0473(7) 0.0279(6) -0.0032(5) 0.0024(5) -0.0002(5) F8 0.0329(7) 0.0313(6) 0.0313(7) 0.0108(5) 0.0105(5) 0.0121(5) F9 0.0260(6) 0.0475(8) 0.0270(6) -0.0006(6) 0.0120(5) 0.0137(5) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag O1 C1 1.354(2) . ? O1 C7 1.450(2) . ? O2 C5 1.352(2) . ? O2 C6 1.442(2) . ? N1 C1 1.321(2) . ? N1 C5 1.326(2) . ? C1 C2 1.396(2) . ? C2 F1 1.3458(19) . ? C2 C3 1.401(2) . ? C3 C4 1.394(2) . ? C3 C8 1.524(2) . ? C4 F2 1.342(2) . ? C4 C5 1.392(3) . ? C6 C7 1.518(3) 3_655 ? C7 C6 1.518(3) 3_655 ? C8 F3 1.379(2) . ? C8 C9 1.546(3) . ? C8 C10 1.570(3) . ? C9 F6 1.327(2) . ? C9 F5 1.329(2) . ? C9 F4 1.340(2) . ? C10 F7 1.324(2) . ? C10 F9 1.331(2) . ? C10 F8 1.332(2) . ? 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 C1 O1 C7 116.60(13) . . ? C5 O2 C6 117.43(13) . . ? C1 N1 C5 119.24(15) . . ? N1 C1 O1 120.93(15) . . ? N1 C1 C2 122.31(15) . . ? O1 C1 C2 116.73(15) . . ? F1 C2 C1 117.64(15) . . ? F1 C2 C3 122.36(15) . . ? C1 C2 C3 120.00(15) . . ? C4 C3 C2 115.75(15) . . ? C4 C3 C8 123.02(15) . . ? C2 C3 C8 121.21(15) . . ? F2 C4 C5 118.36(15) . . ? F2 C4 C3 120.92(16) . . ? C5 C4 C3 120.71(16) . . ? N1 C5 O2 121.05(15) . . ? N1 C5 C4 121.88(16) . . ? O2 C5 C4 117.05(15) . . ? O2 C6 C7 109.66(15) . 3_655 ? O1 C7 C6 108.49(14) . 3_655 ? F3 C8 C3 109.30(14) . . ? F3 C8 C9 105.81(14) . . ? C3 C8 C9 110.35(15) . . ? F3 C8 C10 103.96(14) . . ? C3 C8 C10 115.19(14) . . ? C9 C8 C10 111.61(15) . . ? F6 C9 F5 108.99(15) . . ? F6 C9 F4 107.78(15) . . ? F5 C9 F4 108.13(15) . . ? F6 C9 C8 111.74(16) . . ? F5 C9 C8 111.26(15) . . ? F4 C9 C8 108.81(15) . . ? F7 C10 F9 107.85(15) . . ? F7 C10 F8 109.24(15) . . ? F9 C10 F8 108.04(16) . . ? F7 C10 C8 112.66(15) . . ? F9 C10 C8 108.97(15) . . ? F8 C10 C8 109.96(15) . . ? 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 C5 N1 C1 O1 -175.33(15) . . . . ? C5 N1 C1 C2 2.5(2) . . . . ? C7 O1 C1 N1 -1.8(2) . . . . ? C7 O1 C1 C2 -179.69(15) . . . . ? N1 C1 C2 F1 176.55(15) . . . . ? O1 C1 C2 F1 -5.6(2) . . . . ? N1 C1 C2 C3 -4.0(3) . . . . ? O1 C1 C2 C3 173.85(15) . . . . ? F1 C2 C3 C4 -177.09(15) . . . . ? C1 C2 C3 C4 3.5(2) . . . . ? F1 C2 C3 C8 1.4(3) . . . . ? C1 C2 C3 C8 -177.95(16) . . . . ? C2 C3 C4 F2 178.94(15) . . . . ? C8 C3 C4 F2 0.5(3) . . . . ? C2 C3 C4 C5 -1.8(2) . . . . ? C8 C3 C4 C5 179.70(16) . . . . ? C1 N1 C5 O2 177.46(15) . . . . ? C1 N1 C5 C4 -0.6(2) . . . . ? C6 O2 C5 N1 1.2(2) . . . . ? C6 O2 C5 C4 179.43(15) . . . . ? F2 C4 C5 N1 179.64(15) . . . . ? C3 C4 C5 N1 0.4(3) . . . . ? F2 C4 C5 O2 1.5(2) . . . . ? C3 C4 C5 O2 -177.80(15) . . . . ? C5 O2 C6 C7 91.13(18) . . . 3_655 ? C1 O1 C7 C6 -84.91(18) . . . 3_655 ? C4 C3 C8 F3 -158.50(15) . . . . ? C2 C3 C8 F3 23.1(2) . . . . ? C4 C3 C8 C9 85.5(2) . . . . ? C2 C3 C8 C9 -92.86(19) . . . . ? C4 C3 C8 C10 -41.9(2) . . . . ? C2 C3 C8 C10 139.66(17) . . . . ? F3 C8 C9 F6 64.55(19) . . . . ? C3 C8 C9 F6 -177.33(14) . . . . ? C10 C8 C9 F6 -47.9(2) . . . . ? F3 C8 C9 F5 -173.38(13) . . . . ? C3 C8 C9 F5 -55.3(2) . . . . ? C10 C8 C9 F5 74.18(19) . . . . ? F3 C8 C9 F4 -54.35(18) . . . . ? C3 C8 C9 F4 63.77(18) . . . . ? C10 C8 C9 F4 -166.79(14) . . . . ? F3 C8 C10 F7 -152.64(15) . . . . ? C3 C8 C10 F7 87.81(19) . . . . ? C9 C8 C10 F7 -39.0(2) . . . . ? F3 C8 C10 F9 -32.99(19) . . . . ? C3 C8 C10 F9 -152.55(16) . . . . ? C9 C8 C10 F9 80.61(19) . . . . ? F3 C8 C10 F8 85.25(17) . . . . ? C3 C8 C10 F8 -34.3(2) . . . . ? C9 C8 C10 F8 -161.15(15) . . . . ? _diffrn_measured_fraction_theta_max 0.929 _diffrn_reflns_theta_full 30.31 _diffrn_measured_fraction_theta_full 0.929 _refine_diff_density_max 0.538 _refine_diff_density_min -0.284 _refine_diff_density_rms 0.063