# Electronic Supplementary Material (ESI) for Catalysis Science & Technology # This journal is © The Royal Society of Chemistry 2012 data_global _journal_name_full Cat.Sci.Tech. _journal_coden_Cambridge 1486 _journal_volume ? _journal_page_first ? _journal_year ? _publ_contact_author_name 'Dr Julien Legros' _publ_contact_author_email julien.legros@u-psud.fr _publ_section_title ; Self-assembly between 1,4-diazabicyclo[2.2.2]octane and bis(hexafluoroalcohols): solid/liquid phase switching for catalyst recycling ; loop_ _publ_author_name J.Legros D.Bonnet-Delpon B.Crousse A.Slawin # Attachment '- 1a.cif' data_1a _database_code_depnum_ccdc_archive 'CCDC 855431' #TrackingRef '- 1a.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C6 H12 N2,C12 H6 F12 O2' _chemical_formula_sum 'C18 H18 F12 N2 O2' _chemical_formula_weight 522.34 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0181 0.0091 '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 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' F F 0.0727 0.0534 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Triclinic _symmetry_space_group_name_H-M P-1 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 8.301(3) _cell_length_b 10.979(4) _cell_length_c 11.710(3) _cell_angle_alpha 80.225(12) _cell_angle_beta 85.04(3) _cell_angle_gamma 89.69(2) _cell_volume 1047.7(6) _cell_formula_units_Z 2 _cell_measurement_temperature 173(2) _cell_measurement_reflns_used 1153 _cell_measurement_theta_min 21.2 _cell_measurement_theta_max 68.7 _exptl_crystal_description Platelet _exptl_crystal_colour Colorless _exptl_crystal_size_max 0.20 _exptl_crystal_size_mid 0.10 _exptl_crystal_size_min 0.01 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.656 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 528 _exptl_absorpt_coefficient_mu 1.634 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.763 _exptl_absorpt_correction_T_max 1.000 _exptl_absorpt_process_details 'Jacobson, R. (1998) Private communication' _exptl_special_details ; ? ; _diffrn_ambient_temperature 173(2) _diffrn_radiation_wavelength 1.54178 _diffrn_radiation_type CuK\a _diffrn_radiation_source 'rotating anode' _diffrn_radiation_monochromator confocal _diffrn_measurement_device_type CCD _diffrn_measurement_method '\w scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 14359 _diffrn_reflns_av_R_equivalents 0.0513 _diffrn_reflns_av_sigmaI/netI 0.0379 _diffrn_reflns_limit_h_min -9 _diffrn_reflns_limit_h_max 9 _diffrn_reflns_limit_k_min -13 _diffrn_reflns_limit_k_max 12 _diffrn_reflns_limit_l_min -13 _diffrn_reflns_limit_l_max 13 _diffrn_reflns_theta_min 3.84 _diffrn_reflns_theta_max 68.17 _reflns_number_total 3590 _reflns_number_gt 2942 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'CrystalClear (Rigaku Corp., 2004)' _computing_cell_refinement 'CrystalClear (Rigaku Corp., 2004)' _computing_data_reduction 'CrystalClear (Rigaku Corp., 2004)' _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. The OH hydrogen atoms were located from a difference map and refined isotropically subject to a distance restraint. ; _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^)+(0.0952P)^2^+0.6065P] 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 3590 _refine_ls_number_parameters 315 _refine_ls_number_restraints 2 _refine_ls_R_factor_all 0.0700 _refine_ls_R_factor_gt 0.0590 _refine_ls_wR_factor_ref 0.1770 _refine_ls_wR_factor_gt 0.1634 _refine_ls_goodness_of_fit_ref 1.088 _refine_ls_restrained_S_all 1.088 _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 N1 N 0.4795(3) 0.7204(2) 0.82680(19) 0.0320(5) Uani 1 1 d . . . C2 C 0.5394(5) 0.8135(5) 0.7275(3) 0.0837(16) Uani 1 1 d . . . H2A H 0.6533 0.7956 0.7036 0.100 Uiso 1 1 calc R . . H2B H 0.5362 0.8961 0.7506 0.100 Uiso 1 1 calc R . . C3 C 0.4357(5) 0.8138(5) 0.6237(3) 0.0770(14) Uani 1 1 d . . . H3A H 0.3877 0.8964 0.6027 0.092 Uiso 1 1 calc R . . H3B H 0.5052 0.7963 0.5554 0.092 Uiso 1 1 calc R . . N4 N 0.3069(3) 0.7205(2) 0.65388(19) 0.0326(5) Uani 1 1 d . . . C5 C 0.3128(4) 0.7535(5) 0.8567(3) 0.0758(14) Uani 1 1 d . . . H5A H 0.3106 0.8373 0.8775 0.091 Uiso 1 1 calc R . . H5B H 0.2672 0.6947 0.9254 0.091 Uiso 1 1 calc R . . C6 C 0.2076(4) 0.7512(5) 0.7546(3) 0.0631(11) Uani 1 1 d . . . H6A H 0.1198 0.6890 0.7785 0.076 Uiso 1 1 calc R . . H6B H 0.1576 0.8330 0.7333 0.076 Uiso 1 1 calc R . . C7 C 0.4808(8) 0.6014(4) 0.7914(5) 0.103(2) Uani 1 1 d . . . H7A H 0.4377 0.5385 0.8577 0.124 Uiso 1 1 calc R . . H7B H 0.5936 0.5793 0.7692 0.124 Uiso 1 1 calc R . . C8 C 0.3778(6) 0.5999(4) 0.6872(4) 0.0835(16) Uani 1 1 d . . . H8A H 0.4469 0.5782 0.6205 0.100 Uiso 1 1 calc R . . H8B H 0.2911 0.5366 0.7091 0.100 Uiso 1 1 calc R . . C11 C 0.0237(3) 0.7025(3) 0.2970(2) 0.0289(6) Uani 1 1 d . . . C12 C -0.1022(3) 0.7517(3) 0.2329(2) 0.0292(6) Uani 1 1 d . . . H12A H -0.1640 0.8175 0.2567 0.035 Uiso 1 1 calc R . . C13 C -0.1386(3) 0.7057(3) 0.1343(2) 0.0280(6) Uani 1 1 d . . . C14 C -0.0447(3) 0.6121(3) 0.0987(2) 0.0383(7) Uani 1 1 d . . . H14A H -0.0671 0.5805 0.0310 0.046 Uiso 1 1 calc R . . C15 C 0.0817(4) 0.5648(3) 0.1615(3) 0.0411(7) Uani 1 1 d . . . H15A H 0.1462 0.5013 0.1358 0.049 Uiso 1 1 calc R . . C16 C 0.1161(3) 0.6083(3) 0.2613(2) 0.0342(6) Uani 1 1 d . . . H16A H 0.2020 0.5739 0.3046 0.041 Uiso 1 1 calc R . . C17 C 0.0609(3) 0.7504(3) 0.4075(2) 0.0283(6) Uani 1 1 d . . . O17 O 0.1793(2) 0.67862(19) 0.46160(16) 0.0381(5) Uani 1 1 d D . . H17O H 0.215(5) 0.700(4) 0.5333(19) 0.073(12) Uiso 1 1 d D . . C18 C 0.1232(3) 0.8846(3) 0.3753(2) 0.0352(6) Uani 1 1 d . . . F1 F 0.2585(2) 0.8897(2) 0.3051(2) 0.0650(6) Uani 1 1 d . . . F2 F 0.0199(2) 0.96295(17) 0.32139(16) 0.0504(5) Uani 1 1 d . . . F3 F 0.1587(2) 0.93066(17) 0.46904(16) 0.0521(5) Uani 1 1 d . . . C19 C -0.0925(3) 0.7419(3) 0.4931(2) 0.0378(7) Uani 1 1 d . . . F4 F -0.1586(3) 0.6301(2) 0.50928(18) 0.0660(6) Uani 1 1 d . . . F5 F -0.0602(2) 0.7646(2) 0.59720(14) 0.0606(6) Uani 1 1 d . . . F6 F -0.2085(2) 0.8215(2) 0.45818(15) 0.0511(5) Uani 1 1 d . . . C20 C -0.2777(3) 0.7578(2) 0.0629(2) 0.0284(6) Uani 1 1 d . . . O20 O -0.3170(2) 0.67407(18) -0.00775(16) 0.0352(5) Uani 1 1 d D . . H20O H -0.395(3) 0.707(3) -0.063(2) 0.063(11) Uiso 1 1 d D . . C21 C -0.2227(3) 0.8813(3) -0.0134(2) 0.0370(7) Uani 1 1 d . . . F7 F -0.1028(2) 0.86180(19) -0.09179(15) 0.0569(5) Uani 1 1 d . . . F8 F -0.3427(2) 0.93528(16) -0.07164(16) 0.0509(5) Uani 1 1 d . . . F9 F -0.1679(2) 0.96269(16) 0.04673(15) 0.0475(5) Uani 1 1 d . . . C22 C -0.4306(3) 0.7776(3) 0.1436(2) 0.0326(6) Uani 1 1 d . . . F10 F -0.56161(19) 0.79385(18) 0.08437(15) 0.0467(5) Uani 1 1 d . . . F11 F -0.41897(19) 0.87524(16) 0.19645(15) 0.0431(5) Uani 1 1 d . . . F12 F -0.4603(2) 0.67898(17) 0.22647(15) 0.0473(5) 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 N1 0.0323(11) 0.0357(14) 0.0307(12) -0.0099(10) -0.0091(9) 0.0019(10) C2 0.074(3) 0.123(4) 0.049(2) 0.013(2) -0.0269(19) -0.049(3) C3 0.067(2) 0.114(4) 0.043(2) 0.014(2) -0.0230(18) -0.043(2) N4 0.0314(12) 0.0377(14) 0.0306(12) -0.0088(10) -0.0071(9) 0.0023(10) C5 0.0415(19) 0.151(5) 0.043(2) -0.034(2) -0.0134(15) 0.015(2) C6 0.0421(18) 0.110(3) 0.0428(18) -0.024(2) -0.0148(14) 0.0107(19) C7 0.156(5) 0.064(3) 0.119(4) -0.055(3) -0.113(4) 0.050(3) C8 0.120(4) 0.059(3) 0.093(3) -0.041(2) -0.078(3) 0.042(3) C11 0.0294(13) 0.0308(15) 0.0282(13) -0.0075(11) -0.0074(10) 0.0007(11) C12 0.0295(13) 0.0293(15) 0.0315(14) -0.0106(11) -0.0076(10) 0.0068(11) C13 0.0278(13) 0.0324(15) 0.0266(13) -0.0102(10) -0.0076(10) 0.0037(11) C14 0.0411(16) 0.0455(19) 0.0351(15) -0.0217(13) -0.0133(12) 0.0099(14) C15 0.0418(16) 0.0433(19) 0.0461(17) -0.0232(14) -0.0184(13) 0.0191(14) C16 0.0314(14) 0.0382(17) 0.0368(15) -0.0118(12) -0.0148(11) 0.0106(12) C17 0.0281(13) 0.0316(15) 0.0281(13) -0.0089(11) -0.0110(10) 0.0052(11) O17 0.0430(11) 0.0422(12) 0.0345(11) -0.0135(9) -0.0208(9) 0.0131(9) C18 0.0365(15) 0.0372(17) 0.0352(15) -0.0117(12) -0.0115(12) 0.0014(12) F1 0.0535(12) 0.0593(13) 0.0817(14) -0.0238(11) 0.0220(10) -0.0191(10) F2 0.0672(12) 0.0376(10) 0.0498(11) -0.0052(8) -0.0291(9) 0.0019(9) F3 0.0709(12) 0.0422(11) 0.0527(11) -0.0223(8) -0.0314(9) 0.0044(9) C19 0.0384(15) 0.0496(19) 0.0282(14) -0.0112(12) -0.0091(12) 0.0026(14) F4 0.0742(14) 0.0616(14) 0.0573(12) -0.0049(10) 0.0128(10) -0.0239(11) F5 0.0465(11) 0.1113(18) 0.0297(9) -0.0260(10) -0.0086(8) 0.0105(11) F6 0.0344(9) 0.0811(14) 0.0410(10) -0.0181(9) -0.0066(7) 0.0156(9) C20 0.0318(13) 0.0299(15) 0.0270(13) -0.0112(11) -0.0101(10) 0.0031(11) O20 0.0417(11) 0.0339(11) 0.0365(10) -0.0169(8) -0.0196(8) 0.0087(9) C21 0.0407(15) 0.0366(17) 0.0366(15) -0.0096(12) -0.0134(12) 0.0044(13) F7 0.0633(12) 0.0610(13) 0.0416(10) -0.0023(9) 0.0098(9) 0.0002(10) F8 0.0633(12) 0.0378(11) 0.0528(11) 0.0015(8) -0.0300(9) 0.0044(9) F9 0.0565(11) 0.0382(10) 0.0499(10) -0.0068(8) -0.0167(8) -0.0123(8) C22 0.0305(14) 0.0331(16) 0.0379(15) -0.0115(12) -0.0130(11) 0.0060(12) F10 0.0305(9) 0.0651(13) 0.0514(10) -0.0226(9) -0.0173(7) 0.0107(8) F11 0.0369(9) 0.0483(11) 0.0521(10) -0.0283(8) -0.0103(7) 0.0106(8) F12 0.0429(10) 0.0474(11) 0.0481(10) -0.0001(8) 0.0003(8) -0.0022(8) _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 N1 C7 1.435(4) . ? N1 C5 1.457(4) . ? N1 C2 1.465(5) . ? C2 C3 1.548(5) . ? C2 H2A 0.9900 . ? C2 H2B 0.9900 . ? C3 N4 1.464(4) . ? C3 H3A 0.9900 . ? C3 H3B 0.9900 . ? N4 C8 1.451(5) . ? N4 C6 1.465(4) . ? C5 C6 1.544(5) . ? C5 H5A 0.9900 . ? C5 H5B 0.9900 . ? C6 H6A 0.9900 . ? C6 H6B 0.9900 . ? C7 C8 1.552(5) . ? C7 H7A 0.9900 . ? C7 H7B 0.9900 . ? C8 H8A 0.9900 . ? C8 H8B 0.9900 . ? C11 C16 1.384(4) . ? C11 C12 1.393(4) . ? C11 C17 1.533(3) . ? C12 C13 1.392(3) . ? C12 H12A 0.9500 . ? C13 C14 1.385(4) . ? C13 C20 1.536(3) . ? C14 C15 1.381(4) . ? C14 H14A 0.9500 . ? C15 C16 1.387(4) . ? C15 H15A 0.9500 . ? C16 H16A 0.9500 . ? C17 O17 1.385(3) . ? C17 C18 1.539(4) . ? C17 C19 1.544(4) . ? O17 H17O 0.9800(11) . ? C18 F1 1.328(3) . ? C18 F2 1.332(3) . ? C18 F3 1.339(3) . ? C19 F4 1.325(4) . ? C19 F5 1.334(3) . ? C19 F6 1.340(4) . ? C20 O20 1.394(3) . ? C20 C21 1.539(4) . ? C20 C22 1.553(4) . ? O20 H20O 0.9800(11) . ? C21 F9 1.333(3) . ? C21 F8 1.335(3) . ? C21 F7 1.336(3) . ? C22 F11 1.333(3) . ? C22 F12 1.334(3) . ? C22 F10 1.335(3) . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C7 N1 C5 108.9(4) . . ? C7 N1 C2 109.0(4) . . ? C5 N1 C2 106.0(3) . . ? N1 C2 C3 110.8(3) . . ? N1 C2 H2A 109.5 . . ? C3 C2 H2A 109.5 . . ? N1 C2 H2B 109.5 . . ? C3 C2 H2B 109.5 . . ? H2A C2 H2B 108.1 . . ? N4 C3 C2 110.4(3) . . ? N4 C3 H3A 109.6 . . ? C2 C3 H3A 109.6 . . ? N4 C3 H3B 109.6 . . ? C2 C3 H3B 109.6 . . ? H3A C3 H3B 108.1 . . ? C8 N4 C3 109.3(3) . . ? C8 N4 C6 108.5(3) . . ? C3 N4 C6 107.2(3) . . ? N1 C5 C6 111.4(3) . . ? N1 C5 H5A 109.4 . . ? C6 C5 H5A 109.4 . . ? N1 C5 H5B 109.4 . . ? C6 C5 H5B 109.4 . . ? H5A C5 H5B 108.0 . . ? N4 C6 C5 110.1(3) . . ? N4 C6 H6A 109.6 . . ? C5 C6 H6A 109.6 . . ? N4 C6 H6B 109.6 . . ? C5 C6 H6B 109.6 . . ? H6A C6 H6B 108.1 . . ? N1 C7 C8 111.8(3) . . ? N1 C7 H7A 109.3 . . ? C8 C7 H7A 109.3 . . ? N1 C7 H7B 109.3 . . ? C8 C7 H7B 109.3 . . ? H7A C7 H7B 107.9 . . ? N4 C8 C7 110.0(3) . . ? N4 C8 H8A 109.7 . . ? C7 C8 H8A 109.7 . . ? N4 C8 H8B 109.7 . . ? C7 C8 H8B 109.7 . . ? H8A C8 H8B 108.2 . . ? C16 C11 C12 119.8(2) . . ? C16 C11 C17 119.3(2) . . ? C12 C11 C17 121.0(2) . . ? C13 C12 C11 120.8(2) . . ? C13 C12 H12A 119.6 . . ? C11 C12 H12A 119.6 . . ? C14 C13 C12 119.0(2) . . ? C14 C13 C20 119.2(2) . . ? C12 C13 C20 121.7(2) . . ? C15 C14 C13 120.0(2) . . ? C15 C14 H14A 120.0 . . ? C13 C14 H14A 120.0 . . ? C14 C15 C16 121.2(3) . . ? C14 C15 H15A 119.4 . . ? C16 C15 H15A 119.4 . . ? C11 C16 C15 119.1(3) . . ? C11 C16 H16A 120.4 . . ? C15 C16 H16A 120.4 . . ? O17 C17 C11 109.8(2) . . ? O17 C17 C18 108.6(2) . . ? C11 C17 C18 109.5(2) . . ? O17 C17 C19 108.2(2) . . ? C11 C17 C19 109.9(2) . . ? C18 C17 C19 110.7(2) . . ? C17 O17 H17O 118(2) . . ? F1 C18 F2 107.0(2) . . ? F1 C18 F3 106.8(2) . . ? F2 C18 F3 106.4(2) . . ? F1 C18 C17 110.0(2) . . ? F2 C18 C17 114.3(2) . . ? F3 C18 C17 111.9(2) . . ? F4 C19 F5 107.2(3) . . ? F4 C19 F6 106.4(2) . . ? F5 C19 F6 105.8(2) . . ? F4 C19 C17 110.9(2) . . ? F5 C19 C17 111.9(2) . . ? F6 C19 C17 114.2(2) . . ? O20 C20 C13 109.2(2) . . ? O20 C20 C21 109.5(2) . . ? C13 C20 C21 108.9(2) . . ? O20 C20 C22 108.2(2) . . ? C13 C20 C22 111.0(2) . . ? C21 C20 C22 110.0(2) . . ? C20 O20 H20O 113(2) . . ? F9 C21 F8 107.2(2) . . ? F9 C21 F7 107.0(2) . . ? F8 C21 F7 107.5(2) . . ? F9 C21 C20 113.4(2) . . ? F8 C21 C20 111.6(2) . . ? F7 C21 C20 109.9(2) . . ? F11 C22 F12 107.3(2) . . ? F11 C22 F10 107.0(2) . . ? F12 C22 F10 106.7(2) . . ? F11 C22 C20 113.4(2) . . ? F12 C22 C20 110.8(2) . . ? F10 C22 C20 111.2(2) . . ? 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 C7 N1 C2 C3 57.6(5) . . . . ? C5 N1 C2 C3 -59.4(5) . . . . ? N1 C2 C3 N4 -0.2(6) . . . . ? C2 C3 N4 C8 -57.9(5) . . . . ? C2 C3 N4 C6 59.6(5) . . . . ? C7 N1 C5 C6 -56.2(5) . . . . ? C2 N1 C5 C6 60.9(5) . . . . ? C8 N4 C6 C5 59.6(4) . . . . ? C3 N4 C6 C5 -58.3(4) . . . . ? N1 C5 C6 N4 -2.1(5) . . . . ? C5 N1 C7 C8 57.7(6) . . . . ? C2 N1 C7 C8 -57.5(6) . . . . ? C3 N4 C8 C7 58.3(5) . . . . ? C6 N4 C8 C7 -58.4(5) . . . . ? N1 C7 C8 N4 -0.3(7) . . . . ? C16 C11 C12 C13 1.3(4) . . . . ? C17 C11 C12 C13 -178.2(2) . . . . ? C11 C12 C13 C14 -1.8(4) . . . . ? C11 C12 C13 C20 179.5(2) . . . . ? C12 C13 C14 C15 0.8(4) . . . . ? C20 C13 C14 C15 179.6(3) . . . . ? C13 C14 C15 C16 0.7(5) . . . . ? C12 C11 C16 C15 0.3(4) . . . . ? C17 C11 C16 C15 179.7(3) . . . . ? C14 C15 C16 C11 -1.3(5) . . . . ? C16 C11 C17 O17 -5.6(3) . . . . ? C12 C11 C17 O17 173.8(2) . . . . ? C16 C11 C17 C18 113.6(3) . . . . ? C12 C11 C17 C18 -66.9(3) . . . . ? C16 C11 C17 C19 -124.6(3) . . . . ? C12 C11 C17 C19 54.9(3) . . . . ? O17 C17 C18 F1 58.9(3) . . . . ? C11 C17 C18 F1 -61.0(3) . . . . ? C19 C17 C18 F1 177.7(2) . . . . ? O17 C17 C18 F2 179.4(2) . . . . ? C11 C17 C18 F2 59.4(3) . . . . ? C19 C17 C18 F2 -61.9(3) . . . . ? O17 C17 C18 F3 -59.6(3) . . . . ? C11 C17 C18 F3 -179.5(2) . . . . ? C19 C17 C18 F3 59.2(3) . . . . ? O17 C17 C19 F4 -69.2(3) . . . . ? C11 C17 C19 F4 50.7(3) . . . . ? C18 C17 C19 F4 171.8(2) . . . . ? O17 C17 C19 F5 50.5(3) . . . . ? C11 C17 C19 F5 170.4(2) . . . . ? C18 C17 C19 F5 -68.5(3) . . . . ? O17 C17 C19 F6 170.6(2) . . . . ? C11 C17 C19 F6 -69.5(3) . . . . ? C18 C17 C19 F6 51.6(3) . . . . ? C14 C13 C20 O20 18.4(3) . . . . ? C12 C13 C20 O20 -162.8(2) . . . . ? C14 C13 C20 C21 -101.1(3) . . . . ? C12 C13 C20 C21 77.6(3) . . . . ? C14 C13 C20 C22 137.6(3) . . . . ? C12 C13 C20 C22 -43.6(3) . . . . ? O20 C20 C21 F9 -173.9(2) . . . . ? C13 C20 C21 F9 -54.5(3) . . . . ? C22 C20 C21 F9 67.3(3) . . . . ? O20 C20 C21 F8 65.0(3) . . . . ? C13 C20 C21 F8 -175.7(2) . . . . ? C22 C20 C21 F8 -53.8(3) . . . . ? O20 C20 C21 F7 -54.1(3) . . . . ? C13 C20 C21 F7 65.2(3) . . . . ? C22 C20 C21 F7 -173.0(2) . . . . ? O20 C20 C22 F11 -165.9(2) . . . . ? C13 C20 C22 F11 74.3(3) . . . . ? C21 C20 C22 F11 -46.3(3) . . . . ? O20 C20 C22 F12 73.3(3) . . . . ? C13 C20 C22 F12 -46.4(3) . . . . ? C21 C20 C22 F12 -167.0(2) . . . . ? O20 C20 C22 F10 -45.2(3) . . . . ? C13 C20 C22 F10 -165.0(2) . . . . ? C21 C20 C22 F10 74.4(3) . . . . ? loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA _geom_hbond_site_symmetry_A O17 H17O N4 0.9800(11) 1.708(8) 2.678(3) 169(4) . O20 H20O N1 0.9800(11) 1.712(12) 2.662(3) 162(4) 1_454 _diffrn_measured_fraction_theta_max 0.941 _diffrn_reflns_theta_full 67.00 _diffrn_measured_fraction_theta_full 0.948 _refine_diff_density_max 0.509 _refine_diff_density_min -0.387 _refine_diff_density_rms 0.067 # Attachment '- 1b.cif' data_1b _database_code_depnum_ccdc_archive 'CCDC 855432' #TrackingRef '- 1b.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C6 H12 N2,C12 H6 F12 O2' _chemical_formula_sum 'C18 H18 F12 N2 O2' _chemical_formula_weight 522.34 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0181 0.0091 '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 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' F F 0.0727 0.0534 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Monoclinic _symmetry_space_group_name_H-M Cc 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 25.06(2) _cell_length_b 6.782(5) _cell_length_c 13.057(15) _cell_angle_alpha 90.00 _cell_angle_beta 110.81(3) _cell_angle_gamma 90.00 _cell_volume 2075(3) _cell_formula_units_Z 4 _cell_measurement_temperature 173(2) _cell_measurement_reflns_used 1264 _cell_measurement_theta_min 21.7 _cell_measurement_theta_max 68.5 _exptl_crystal_description Prism _exptl_crystal_colour Colorless _exptl_crystal_size_max 0.12 _exptl_crystal_size_mid 0.10 _exptl_crystal_size_min 0.05 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.672 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1056 _exptl_absorpt_coefficient_mu 1.650 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.643 _exptl_absorpt_correction_T_max 1.000 _exptl_absorpt_process_details 'Jacobson, R. (1998) Private communication' _exptl_special_details ; ? ; _diffrn_ambient_temperature 173(2) _diffrn_radiation_wavelength 1.54178 _diffrn_radiation_type CuK\a _diffrn_radiation_source 'rotating anode' _diffrn_radiation_monochromator confocal _diffrn_measurement_device_type CCD _diffrn_measurement_method '\w scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 12652 _diffrn_reflns_av_R_equivalents 0.1548 _diffrn_reflns_av_sigmaI/netI 0.0797 _diffrn_reflns_limit_h_min -30 _diffrn_reflns_limit_h_max 30 _diffrn_reflns_limit_k_min -8 _diffrn_reflns_limit_k_max 8 _diffrn_reflns_limit_l_min -15 _diffrn_reflns_limit_l_max 15 _diffrn_reflns_theta_min 3.77 _diffrn_reflns_theta_max 67.84 _reflns_number_total 3574 _reflns_number_gt 2892 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'CrystalClear (Rigaku Corp., 2004)' _computing_cell_refinement 'CrystalClear (Rigaku Corp., 2004)' _computing_data_reduction 'CrystalClear (Rigaku Corp., 2004)' _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. The OH hydrogen atoms were located from a difference map and refined isotropically subject to a distance restraint. ; _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^)+(0.2000P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment mixed _refine_ls_extinction_method SHELXL _refine_ls_extinction_coef 0.014(2) _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _refine_ls_abs_structure_Flack 0.6(3) _refine_ls_number_reflns 3574 _refine_ls_number_parameters 316 _refine_ls_number_restraints 4 _refine_ls_R_factor_all 0.1404 _refine_ls_R_factor_gt 0.1324 _refine_ls_wR_factor_ref 0.3567 _refine_ls_wR_factor_gt 0.3253 _refine_ls_goodness_of_fit_ref 1.330 _refine_ls_restrained_S_all 1.329 _refine_ls_shift/su_max 0.013 _refine_ls_shift/su_mean 0.001 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 N1 N 0.5091(2) 0.4088(9) 1.0467(5) 0.0683(13) Uani 1 1 d . . . C2 C 0.5387(4) 0.2583(11) 1.1265(6) 0.0797(17) Uani 1 1 d . . . H2A H 0.5562 0.1594 1.0923 0.096 Uiso 1 1 calc R . . H2B H 0.5115 0.1898 1.1539 0.096 Uiso 1 1 calc R . . C3 C 0.5855(4) 0.3631(12) 1.2223(6) 0.0814(19) Uani 1 1 d . . . H3A H 0.5781 0.3408 1.2909 0.098 Uiso 1 1 calc R . . H3B H 0.6231 0.3043 1.2314 0.098 Uiso 1 1 calc R . . N4 N 0.5876(2) 0.5727(8) 1.2040(5) 0.0688(13) Uani 1 1 d . . . C5 C 0.5496(3) 0.5063(12) 1.0072(6) 0.0788(18) Uani 1 1 d . . . H5A H 0.5293 0.6058 0.9515 0.095 Uiso 1 1 calc R . . H5B H 0.5666 0.4080 0.9717 0.095 Uiso 1 1 calc R . . C6 C 0.5970(4) 0.6067(14) 1.1003(6) 0.085(2) Uani 1 1 d . . . H6A H 0.6345 0.5525 1.1053 0.103 Uiso 1 1 calc R . . H6B H 0.5970 0.7500 1.0858 0.103 Uiso 1 1 calc R . . C7 C 0.4840(3) 0.5565(13) 1.0981(6) 0.0804(19) Uani 1 1 d . . . H7A H 0.4564 0.4925 1.1260 0.097 Uiso 1 1 calc R . . H7B H 0.4634 0.6568 1.0433 0.097 Uiso 1 1 calc R . . C8 C 0.5312(3) 0.6551(12) 1.1923(6) 0.0806(18) Uani 1 1 d . . . H8A H 0.5311 0.7987 1.1786 0.097 Uiso 1 1 calc R . . H8B H 0.5239 0.6351 1.2613 0.097 Uiso 1 1 calc R . . C11 C 0.3454(3) 0.1982(11) 0.7220(5) 0.0679(14) Uani 1 1 d . . . C12 C 0.3083(3) 0.0478(11) 0.6673(6) 0.0757(17) Uani 1 1 d . . . H12A H 0.3149 -0.0831 0.6948 0.091 Uiso 1 1 calc R . . C13 C 0.2619(3) 0.0876(10) 0.5727(6) 0.0692(15) Uani 1 1 d . . . H13A H 0.2369 -0.0165 0.5366 0.083 Uiso 1 1 calc R . . C14 C 0.2516(2) 0.2740(10) 0.5308(5) 0.0641(14) Uani 1 1 d . . . C15 C 0.2891(3) 0.4288(11) 0.5853(6) 0.0749(17) Uani 1 1 d . . . H15A H 0.2826 0.5597 0.5579 0.090 Uiso 1 1 calc R . . C16 C 0.3352(3) 0.3854(11) 0.6794(6) 0.0767(17) Uani 1 1 d . . . H16A H 0.3607 0.4884 0.7155 0.092 Uiso 1 1 calc R . . C17 C 0.3962(3) 0.1629(10) 0.8297(5) 0.0680(15) Uani 1 1 d . . . O17 O 0.4302(2) 0.3304(8) 0.8545(4) 0.0836(14) Uani 1 1 d D . . H17O H 0.460(3) 0.351(13) 0.926(4) 0.09(3) Uiso 1 1 d D . . C18 C 0.4327(3) -0.0040(13) 0.8162(7) 0.087(2) Uani 1 1 d . . . F1 F 0.4465(3) 0.0264(16) 0.7272(5) 0.150(3) Uani 1 1 d . . . F2 F 0.4829(2) -0.0154(8) 0.9012(5) 0.0999(16) Uani 1 1 d . . . F3 F 0.4102(4) -0.1802(9) 0.8095(9) 0.184(5) Uani 1 1 d . . . C19 C 0.3742(3) 0.119(2) 0.9199(7) 0.103(3) Uani 1 1 d . . . F4 F 0.4163(2) 0.0786(11) 1.0155(4) 0.1090(19) Uani 1 1 d . . . F5 F 0.3386(4) -0.017(2) 0.9028(5) 0.242(8) Uani 1 1 d . . . F6 F 0.3496(3) 0.278(2) 0.9422(6) 0.184(5) Uani 1 1 d . . . C20 C 0.1995(2) 0.3132(9) 0.4287(5) 0.0623(13) Uani 1 1 d . . . O20 O 0.1709(2) 0.1381(7) 0.3944(4) 0.0831(14) Uani 1 1 d D . . H20O H 0.136(3) 0.097(17) 0.334(7) 0.12(4) Uiso 1 1 d D . . C21 C 0.1587(3) 0.4478(12) 0.4579(6) 0.0752(17) Uani 1 1 d . . . F7 F 0.1471(2) 0.3769(10) 0.5425(4) 0.1046(17) Uani 1 1 d . . . F8 F 0.1078(2) 0.4638(8) 0.3750(4) 0.0889(13) Uani 1 1 d . . . F9 F 0.1766(2) 0.6312(8) 0.4829(5) 0.1039(17) Uani 1 1 d . . . C22 C 0.2167(4) 0.4029(13) 0.3388(6) 0.0807(18) Uani 1 1 d . . . F10 F 0.2405(3) 0.5839(10) 0.3618(4) 0.1120(19) Uani 1 1 d . . . F11 F 0.1711(2) 0.4315(7) 0.2468(4) 0.0877(13) Uani 1 1 d . . . F12 F 0.2502(4) 0.2834(15) 0.3116(6) 0.149(3) 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 N1 0.061(3) 0.081(3) 0.053(3) -0.001(2) 0.007(2) -0.005(2) C2 0.073(3) 0.078(4) 0.069(4) 0.003(3) 0.001(3) -0.005(3) C3 0.075(4) 0.091(4) 0.057(4) -0.006(3) -0.003(3) -0.010(3) N4 0.068(3) 0.075(3) 0.054(3) -0.003(2) 0.010(2) -0.004(2) C5 0.080(4) 0.096(4) 0.051(4) -0.003(3) 0.013(3) -0.016(4) C6 0.086(5) 0.114(6) 0.050(4) -0.002(3) 0.016(4) -0.020(4) C7 0.061(3) 0.109(5) 0.056(4) -0.002(3) 0.001(3) 0.007(3) C8 0.074(4) 0.092(4) 0.063(4) -0.007(3) 0.009(3) 0.006(3) C11 0.062(3) 0.082(4) 0.051(3) 0.000(3) 0.009(3) 0.002(3) C12 0.068(4) 0.081(4) 0.062(4) -0.002(3) 0.004(3) -0.009(3) C13 0.061(3) 0.078(3) 0.057(4) -0.006(3) 0.007(3) -0.004(3) C14 0.054(3) 0.075(3) 0.049(3) -0.003(2) 0.000(2) -0.006(3) C15 0.066(4) 0.074(4) 0.070(4) -0.006(3) 0.007(3) -0.012(3) C16 0.068(4) 0.091(4) 0.057(4) 0.000(3) 0.004(3) -0.006(3) C17 0.068(4) 0.076(3) 0.053(3) -0.008(3) 0.012(3) -0.007(3) O17 0.076(3) 0.089(3) 0.059(3) 0.008(2) -0.009(2) -0.015(3) C18 0.072(4) 0.096(5) 0.063(4) -0.020(3) -0.012(3) 0.006(4) F1 0.105(4) 0.259(9) 0.071(4) -0.035(4) 0.015(3) 0.052(5) F2 0.072(3) 0.110(3) 0.091(4) -0.015(2) -0.004(3) 0.016(2) F3 0.138(6) 0.083(3) 0.226(10) -0.027(5) -0.064(6) 0.010(3) C19 0.061(4) 0.196(11) 0.047(4) 0.005(5) 0.013(3) -0.013(5) F4 0.084(3) 0.172(5) 0.056(3) 0.015(3) 0.006(2) -0.030(3) F5 0.167(8) 0.48(2) 0.050(3) 0.015(6) 0.009(4) -0.203(12) F6 0.129(6) 0.340(15) 0.077(4) -0.005(6) 0.031(4) 0.095(8) C20 0.056(3) 0.067(3) 0.052(3) -0.001(2) 0.004(3) -0.004(2) O20 0.084(3) 0.075(3) 0.069(3) -0.006(2) 0.001(3) -0.007(2) C21 0.066(4) 0.090(4) 0.060(4) -0.004(3) 0.011(3) -0.006(3) F7 0.089(3) 0.160(5) 0.068(3) 0.010(3) 0.032(2) 0.000(3) F8 0.070(3) 0.108(3) 0.073(3) -0.004(2) 0.007(2) 0.007(2) F9 0.085(3) 0.093(3) 0.118(4) -0.028(3) 0.016(3) 0.003(2) C22 0.076(4) 0.104(5) 0.051(3) 0.007(3) 0.009(3) 0.001(4) F10 0.107(4) 0.144(4) 0.073(3) 0.008(3) 0.017(3) -0.049(3) F11 0.085(3) 0.105(3) 0.056(2) 0.0092(19) 0.004(2) -0.012(2) F12 0.148(6) 0.220(9) 0.097(4) 0.039(5) 0.065(4) 0.083(6) _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 N1 C5 1.451(10) . ? N1 C2 1.459(10) . ? N1 C7 1.466(10) . ? C2 C3 1.550(10) . ? C2 H2A 0.9900 . ? C2 H2B 0.9900 . ? C3 N4 1.446(10) . ? C3 H3A 0.9900 . ? C3 H3B 0.9900 . ? N4 C6 1.474(10) . ? N4 C8 1.476(10) . ? C5 C6 1.525(11) . ? C5 H5A 0.9900 . ? C5 H5B 0.9900 . ? C6 H6A 0.9900 . ? C6 H6B 0.9900 . ? C7 C8 1.525(11) . ? C7 H7A 0.9900 . ? C7 H7B 0.9900 . ? C8 H8A 0.9900 . ? C8 H8B 0.9900 . ? C11 C16 1.373(11) . ? C11 C12 1.393(11) . ? C11 C17 1.544(10) . ? C12 C13 1.390(10) . ? C12 H12A 0.9500 . ? C13 C14 1.365(10) . ? C13 H13A 0.9500 . ? C14 C15 1.420(9) . ? C14 C20 1.522(8) . ? C15 C16 1.388(10) . ? C15 H15A 0.9500 . ? C16 H16A 0.9500 . ? C17 O17 1.388(8) . ? C17 C19 1.496(10) . ? C17 C18 1.504(11) . ? O17 H17O 0.98(2) . ? C18 F3 1.312(12) . ? C18 F1 1.341(12) . ? C18 F2 1.352(9) . ? C19 F5 1.247(13) . ? C19 F6 1.325(16) . ? C19 F4 1.345(10) . ? C20 O20 1.377(8) . ? C20 C22 1.515(10) . ? C20 C21 1.517(10) . ? O20 H20O 0.98(2) . ? C21 F9 1.324(9) . ? C21 F7 1.328(9) . ? C21 F8 1.353(9) . ? C22 F12 1.303(12) . ? C22 F11 1.347(9) . ? C22 F10 1.351(11) . ? 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 N1 C2 109.3(6) . . ? C5 N1 C7 108.6(6) . . ? C2 N1 C7 110.1(6) . . ? N1 C2 C3 107.6(6) . . ? N1 C2 H2A 110.2 . . ? C3 C2 H2A 110.2 . . ? N1 C2 H2B 110.2 . . ? C3 C2 H2B 110.2 . . ? H2A C2 H2B 108.5 . . ? N4 C3 C2 112.3(6) . . ? N4 C3 H3A 109.1 . . ? C2 C3 H3A 109.1 . . ? N4 C3 H3B 109.1 . . ? C2 C3 H3B 109.1 . . ? H3A C3 H3B 107.9 . . ? C3 N4 C6 109.4(6) . . ? C3 N4 C8 107.5(6) . . ? C6 N4 C8 107.8(6) . . ? N1 C5 C6 111.4(6) . . ? N1 C5 H5A 109.3 . . ? C6 C5 H5A 109.3 . . ? N1 C5 H5B 109.3 . . ? C6 C5 H5B 109.3 . . ? H5A C5 H5B 108.0 . . ? N4 C6 C5 109.2(6) . . ? N4 C6 H6A 109.8 . . ? C5 C6 H6A 109.8 . . ? N4 C6 H6B 109.8 . . ? C5 C6 H6B 109.8 . . ? H6A C6 H6B 108.3 . . ? N1 C7 C8 109.5(6) . . ? N1 C7 H7A 109.8 . . ? C8 C7 H7A 109.8 . . ? N1 C7 H7B 109.8 . . ? C8 C7 H7B 109.8 . . ? H7A C7 H7B 108.2 . . ? N4 C8 C7 110.9(6) . . ? N4 C8 H8A 109.5 . . ? C7 C8 H8A 109.5 . . ? N4 C8 H8B 109.5 . . ? C7 C8 H8B 109.5 . . ? H8A C8 H8B 108.0 . . ? C16 C11 C12 118.4(7) . . ? C16 C11 C17 119.1(6) . . ? C12 C11 C17 122.5(6) . . ? C13 C12 C11 120.6(7) . . ? C13 C12 H12A 119.7 . . ? C11 C12 H12A 119.7 . . ? C14 C13 C12 121.0(6) . . ? C14 C13 H13A 119.5 . . ? C12 C13 H13A 119.5 . . ? C13 C14 C15 119.1(6) . . ? C13 C14 C20 119.6(5) . . ? C15 C14 C20 121.3(6) . . ? C16 C15 C14 118.8(7) . . ? C16 C15 H15A 120.6 . . ? C14 C15 H15A 120.6 . . ? C11 C16 C15 122.1(7) . . ? C11 C16 H16A 119.0 . . ? C15 C16 H16A 119.0 . . ? O17 C17 C19 110.3(7) . . ? O17 C17 C18 107.1(6) . . ? C19 C17 C18 110.5(8) . . ? O17 C17 C11 109.0(6) . . ? C19 C17 C11 109.4(6) . . ? C18 C17 C11 110.5(5) . . ? C17 O17 H17O 123(5) . . ? F3 C18 F1 108.6(9) . . ? F3 C18 F2 104.8(7) . . ? F1 C18 F2 105.6(7) . . ? F3 C18 C17 115.3(8) . . ? F1 C18 C17 109.9(8) . . ? F2 C18 C17 112.0(6) . . ? F5 C19 F6 106.2(11) . . ? F5 C19 F4 107.0(9) . . ? F6 C19 F4 103.5(8) . . ? F5 C19 C17 116.6(8) . . ? F6 C19 C17 110.0(9) . . ? F4 C19 C17 112.6(6) . . ? O20 C20 C22 110.6(6) . . ? O20 C20 C21 106.3(5) . . ? C22 C20 C21 110.9(6) . . ? O20 C20 C14 108.6(5) . . ? C22 C20 C14 111.0(5) . . ? C21 C20 C14 109.2(6) . . ? C20 O20 H20O 136(7) . . ? F9 C21 F7 106.8(7) . . ? F9 C21 F8 105.3(7) . . ? F7 C21 F8 105.8(6) . . ? F9 C21 C20 115.3(6) . . ? F7 C21 C20 110.9(6) . . ? F8 C21 C20 112.1(6) . . ? F12 C22 F11 105.8(7) . . ? F12 C22 F10 110.5(8) . . ? F11 C22 F10 103.6(6) . . ? F12 C22 C20 110.4(7) . . ? F11 C22 C20 111.3(6) . . ? F10 C22 C20 114.6(6) . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag C5 N1 C2 C3 60.2(8) . . . . ? C7 N1 C2 C3 -59.0(8) . . . . ? N1 C2 C3 N4 -1.7(10) . . . . ? C2 C3 N4 C6 -57.2(9) . . . . ? C2 C3 N4 C8 59.6(9) . . . . ? C2 N1 C5 C6 -60.6(9) . . . . ? C7 N1 C5 C6 59.5(9) . . . . ? C3 N4 C6 C5 57.4(9) . . . . ? C8 N4 C6 C5 -59.3(9) . . . . ? N1 C5 C6 N4 0.5(10) . . . . ? C5 N1 C7 C8 -59.1(8) . . . . ? C2 N1 C7 C8 60.5(9) . . . . ? C3 N4 C8 C7 -58.3(8) . . . . ? C6 N4 C8 C7 59.6(9) . . . . ? N1 C7 C8 N4 -0.2(9) . . . . ? C16 C11 C12 C13 -0.9(10) . . . . ? C17 C11 C12 C13 177.6(6) . . . . ? C11 C12 C13 C14 0.4(11) . . . . ? C12 C13 C14 C15 -0.1(10) . . . . ? C12 C13 C14 C20 -178.6(6) . . . . ? C13 C14 C15 C16 0.3(10) . . . . ? C20 C14 C15 C16 178.7(6) . . . . ? C12 C11 C16 C15 1.1(11) . . . . ? C17 C11 C16 C15 -177.5(6) . . . . ? C14 C15 C16 C11 -0.8(11) . . . . ? C16 C11 C17 O17 -11.1(9) . . . . ? C12 C11 C17 O17 170.4(6) . . . . ? C16 C11 C17 C19 109.5(9) . . . . ? C12 C11 C17 C19 -69.0(9) . . . . ? C16 C11 C17 C18 -128.6(8) . . . . ? C12 C11 C17 C18 52.9(9) . . . . ? O17 C17 C18 F3 169.7(8) . . . . ? C19 C17 C18 F3 49.5(10) . . . . ? C11 C17 C18 F3 -71.7(10) . . . . ? O17 C17 C18 F1 -67.1(8) . . . . ? C19 C17 C18 F1 172.7(7) . . . . ? C11 C17 C18 F1 51.5(8) . . . . ? O17 C17 C18 F2 49.9(9) . . . . ? C19 C17 C18 F2 -70.3(9) . . . . ? C11 C17 C18 F2 168.5(6) . . . . ? O17 C17 C19 F5 173.2(12) . . . . ? C18 C17 C19 F5 -68.5(13) . . . . ? C11 C17 C19 F5 53.3(14) . . . . ? O17 C17 C19 F6 52.2(9) . . . . ? C18 C17 C19 F6 170.5(7) . . . . ? C11 C17 C19 F6 -67.6(9) . . . . ? O17 C17 C19 F4 -62.6(11) . . . . ? C18 C17 C19 F4 55.7(11) . . . . ? C11 C17 C19 F4 177.5(8) . . . . ? C13 C14 C20 O20 -0.9(8) . . . . ? C15 C14 C20 O20 -179.4(6) . . . . ? C13 C14 C20 C22 -122.8(7) . . . . ? C15 C14 C20 C22 58.7(8) . . . . ? C13 C14 C20 C21 114.7(7) . . . . ? C15 C14 C20 C21 -63.8(7) . . . . ? O20 C20 C21 F9 -173.8(6) . . . . ? C22 C20 C21 F9 -53.4(9) . . . . ? C14 C20 C21 F9 69.2(8) . . . . ? O20 C20 C21 F7 64.7(7) . . . . ? C22 C20 C21 F7 -175.0(6) . . . . ? C14 C20 C21 F7 -52.4(7) . . . . ? O20 C20 C21 F8 -53.3(7) . . . . ? C22 C20 C21 F8 67.0(7) . . . . ? C14 C20 C21 F8 -170.4(5) . . . . ? O20 C20 C22 F12 -60.1(9) . . . . ? C21 C20 C22 F12 -177.8(7) . . . . ? C14 C20 C22 F12 60.6(9) . . . . ? O20 C20 C22 F11 57.1(8) . . . . ? C21 C20 C22 F11 -60.6(8) . . . . ? C14 C20 C22 F11 177.8(6) . . . . ? O20 C20 C22 F10 174.3(7) . . . . ? C21 C20 C22 F10 56.6(9) . . . . ? C14 C20 C22 F10 -65.0(9) . . . . ? loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA _geom_hbond_site_symmetry_A O17 H17O N1 0.98(2) 1.66(2) 2.639(8) 174(8) . O20 H20O N4 0.98(2) 1.71(5) 2.655(7) 160(11) 3_444 _diffrn_measured_fraction_theta_max 0.989 _diffrn_reflns_theta_full 67.00 _diffrn_measured_fraction_theta_full 0.990 _refine_diff_density_max 0.826 _refine_diff_density_min -0.594 _refine_diff_density_rms 0.166