# Electronic Supplementary Material (ESI) for Chemical Science # This journal is © The Royal Society of Chemistry 2013 ####################################################################### # # Cambridge Crystallographic Data Centre # CCDC # ####################################################################### # # This CIF contains data from an original supplementary publication # deposited with the CCDC, and may include chemical, crystal, # experimental, refinement, atomic coordinates, # anisotropic displacement parameters and molecular geometry data, # as required by the journal to which it was submitted. # # This CIF is provided on the understanding that it is used for bona # fide research purposes only. It may contain copyright material # of the CCDC or of third parties, and may not be copied or further # disseminated in any form, whether machine-readable or not, # except for the purpose of generating routine backup copies # on your local computer system. # # For further information on the CCDC, data deposition and # data retrieval see: # www.ccdc.cam.ac.uk # # Bona fide researchers may freely download Mercury and enCIFer # from this site to visualise CIF-encoded structures and # to carry out CIF format checking respectively. # data_shelxl _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C20 H16 F3 N3 O2, H2 O' _chemical_formula_sum 'C20 H18 F3 N3 O3' _chemical_formula_weight 405.37 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 C2/c loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y, -z+1/2' 'x+1/2, y+1/2, z' '-x+1/2, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y, z-1/2' '-x+1/2, -y+1/2, -z' 'x+1/2, -y+1/2, z-1/2' _cell_length_a 27.371(2) _cell_length_b 7.0453(6) _cell_length_c 18.8951(14) _cell_angle_alpha 90.00 _cell_angle_beta 99.010(7) _cell_angle_gamma 90.00 _cell_volume 3598.8(5) _cell_formula_units_Z 8 _cell_measurement_temperature 153(2) _cell_measurement_reflns_used 2403 _cell_measurement_theta_min 2.1 _cell_measurement_theta_max 21.1 _exptl_crystal_description ? _exptl_crystal_colour ? _exptl_crystal_size_max ? _exptl_crystal_size_mid ? _exptl_crystal_size_min ? _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.496 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1680 _exptl_absorpt_coefficient_mu 0.123 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.865 _exptl_absorpt_correction_T_max 1.00 _exptl_absorpt_process_details ; SADABS. Apex II release 2010, Bruker AXS, Inc. ; _exptl_special_details ; ? ; _diffrn_ambient_temperature 153(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 'Nonius KappaCCD with Bruker Apex II detector' _diffrn_measurement_method '\w and \f-scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 32499 _diffrn_reflns_av_R_equivalents 0.1522 _diffrn_reflns_av_sigmaI/netI 0.1347 _diffrn_reflns_limit_h_min -32 _diffrn_reflns_limit_h_max 32 _diffrn_reflns_limit_k_min -8 _diffrn_reflns_limit_k_max 8 _diffrn_reflns_limit_l_min -22 _diffrn_reflns_limit_l_max 22 _diffrn_reflns_theta_min 2.18 _diffrn_reflns_theta_max 24.97 _reflns_number_total 3159 _reflns_number_gt 1517 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Apex II release 2010, Bruker AXS, Inc.' _computing_cell_refinement 'Apex II release 2010, Bruker AXS, Inc.' _computing_data_reduction 'Apex II release 2010, Bruker AXS, Inc.' _computing_structure_solution ; SIR97 - Altomare A., Burla M.C., Camalli M., Cascarano G.L., Giacovazzo C., Guagliardi A., Moliterni A.G.G., Polidori G.,Spagna R. ; _computing_structure_refinement 'XL SHELXTL/PC, Siemens Analytical' _computing_molecular_graphics 'XP SHELXTL/PC, Siemens Analytical' _computing_publication_material ? _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0117P)^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 0.00102(9) _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_number_reflns 3159 _refine_ls_number_parameters 276 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.1192 _refine_ls_R_factor_gt 0.0421 _refine_ls_wR_factor_ref 0.0670 _refine_ls_wR_factor_gt 0.0595 _refine_ls_goodness_of_fit_ref 0.967 _refine_ls_restrained_S_all 0.967 _refine_ls_shift/su_max 0.007 _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 C1 C 0.30917(10) 0.5279(4) 0.42576(15) 0.0180(8) Uani 1 1 d . . . C2 C 0.27302(10) 0.5141(4) 0.47575(14) 0.0141(7) Uani 1 1 d . . . C3 C 0.28821(9) 0.5523(4) 0.54683(14) 0.0172(7) Uani 1 1 d . . . H3 H 0.3216 0.5874 0.5632 0.021 Uiso 1 1 calc R . . C4 C 0.25461(9) 0.5398(4) 0.59554(14) 0.0185(8) Uani 1 1 d . . . H4 H 0.2655 0.5645 0.6449 0.022 Uiso 1 1 calc R . . C5 C 0.20637(10) 0.4923(4) 0.57255(14) 0.0171(7) Uani 1 1 d . . . H5 H 0.1842 0.4848 0.6064 0.020 Uiso 1 1 calc R . . C6 C 0.18861(9) 0.4540(4) 0.49961(14) 0.0150(7) Uani 1 1 d . . . C7 C 0.13881(9) 0.4028(4) 0.47180(15) 0.0163(7) Uani 1 1 d . . . C8 C 0.12622(10) 0.3569(4) 0.40054(15) 0.0197(8) Uani 1 1 d . . . H8 H 0.0935 0.3157 0.3831 0.024 Uiso 1 1 calc R . . C9 C 0.16064(10) 0.3696(4) 0.35299(15) 0.0191(8) Uani 1 1 d . . . H9 H 0.1508 0.3406 0.3037 0.023 Uiso 1 1 calc R . . C10 C 0.20839(10) 0.4237(4) 0.37751(14) 0.0144(7) Uani 1 1 d . . . C11 C 0.24368(10) 0.4404(4) 0.32569(15) 0.0175(7) Uani 1 1 d . . . C12 C 0.22348(9) 0.4638(4) 0.45060(14) 0.0139(7) Uani 1 1 d . . . C13 C 0.32717(9) 0.5149(4) 0.30191(13) 0.0187(8) Uani 1 1 d . . . H13A H 0.3535 0.6056 0.3215 0.022 Uiso 1 1 calc R . . H13B H 0.3095 0.5686 0.2566 0.022 Uiso 1 1 calc R . . C14 C 0.35070(10) 0.3282(4) 0.28610(14) 0.0224(8) Uani 1 1 d . . . H14A H 0.3244 0.2337 0.2709 0.027 Uiso 1 1 calc R . . H14B H 0.3711 0.2806 0.3304 0.027 Uiso 1 1 calc R . . C15 C 0.38324(10) 0.3478(4) 0.22718(14) 0.0260(8) Uani 1 1 d . . . H15A H 0.3933 0.2196 0.2137 0.031 Uiso 1 1 calc R . . H15B H 0.3633 0.4055 0.1843 0.031 Uiso 1 1 calc R . . C16 C 0.42921(10) 0.4670(4) 0.24899(15) 0.0371(9) Uani 1 1 d . . . H16A H 0.4196 0.5956 0.2610 0.056 Uiso 1 1 calc R . . H16B H 0.4483 0.4728 0.2092 0.056 Uiso 1 1 calc R . . H16C H 0.4495 0.4098 0.2909 0.056 Uiso 1 1 calc R . . C17 C 0.10031(10) 0.4052(4) 0.51873(14) 0.0178(7) Uani 1 1 d . . . C18 C 0.08932(9) 0.5320(4) 0.56882(13) 0.0179(7) Uani 1 1 d . . . H18 H 0.1068 0.6446 0.5846 0.021 Uiso 1 1 calc R . . C19 C 0.04713(10) 0.4604(4) 0.59152(14) 0.0178(7) Uani 1 1 d . . . C20 C 0.02039(11) 0.5376(5) 0.64690(16) 0.0265(8) Uani 1 1 d . . . N1 N 0.29217(8) 0.4943(3) 0.35339(11) 0.0142(6) Uani 1 1 d . . . N2 N 0.06504(8) 0.2671(4) 0.51357(13) 0.0220(7) Uani 1 1 d . . . N3 N 0.03172(8) 0.2979(3) 0.55859(12) 0.0230(7) Uani 1 1 d . . . O1 O 0.35265(6) 0.5698(3) 0.44528(9) 0.0228(5) Uani 1 1 d . . . O2 O 0.23196(6) 0.4088(3) 0.26155(10) 0.0231(5) Uani 1 1 d . . . O1W O 0.44058(11) 0.5758(4) 0.55606(13) 0.0299(6) Uani 1 1 d . . . F1 F 0.00419(6) 0.7159(3) 0.63248(9) 0.0368(5) Uani 1 1 d . . . F2 F -0.01911(6) 0.4340(3) 0.65584(9) 0.0474(6) Uani 1 1 d . . . F3 F 0.04948(6) 0.5474(3) 0.71124(8) 0.0386(5) Uani 1 1 d . . . H1WA H 0.4721(15) 0.643(6) 0.559(2) 0.125(18) Uiso 1 1 d . . . H2N H 0.0632(10) 0.154(4) 0.4873(15) 0.048(11) Uiso 1 1 d . . . H1WB H 0.4208(15) 0.636(6) 0.534(2) 0.11(2) 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 C1 0.0204(19) 0.0128(19) 0.021(2) 0.0024(16) 0.0042(16) 0.0025(16) C2 0.0168(17) 0.0103(19) 0.0158(18) 0.0027(14) 0.0046(15) -0.0001(14) C3 0.0149(16) 0.0163(19) 0.0192(18) 0.0000(16) -0.0010(15) 0.0012(14) C4 0.0214(18) 0.020(2) 0.0130(17) 0.0004(15) 0.0009(15) 0.0023(16) C5 0.0202(18) 0.0181(19) 0.0141(18) 0.0037(15) 0.0066(14) 0.0051(15) C6 0.0186(17) 0.0097(17) 0.0173(18) 0.0036(15) 0.0043(15) 0.0019(15) C7 0.0114(17) 0.0170(19) 0.0214(19) 0.0023(15) 0.0049(15) -0.0001(14) C8 0.0130(17) 0.021(2) 0.024(2) -0.0011(15) 0.0014(16) -0.0009(14) C9 0.0210(19) 0.019(2) 0.0178(19) -0.0006(15) 0.0032(16) 0.0028(15) C10 0.0130(17) 0.0144(18) 0.0170(19) 0.0017(15) 0.0056(15) 0.0002(15) C11 0.0182(18) 0.0140(18) 0.0206(19) 0.0005(16) 0.0042(16) 0.0019(15) C12 0.0142(17) 0.0110(18) 0.0172(18) 0.0011(15) 0.0048(15) 0.0005(14) C13 0.0163(16) 0.023(2) 0.0181(18) 0.0021(15) 0.0073(14) -0.0022(15) C14 0.0210(17) 0.023(2) 0.0240(19) 0.0000(15) 0.0068(15) 0.0021(15) C15 0.0230(18) 0.029(2) 0.027(2) -0.0032(16) 0.0093(16) 0.0048(16) C16 0.0247(19) 0.050(3) 0.039(2) 0.0016(19) 0.0138(16) -0.0037(18) C17 0.0125(17) 0.020(2) 0.0205(19) 0.0011(16) 0.0018(15) -0.0034(16) C18 0.0185(17) 0.0144(18) 0.0213(18) -0.0047(15) 0.0051(14) -0.0047(15) C19 0.0158(18) 0.0193(19) 0.0187(18) -0.0007(16) 0.0041(15) 0.0007(16) C20 0.0230(19) 0.027(2) 0.030(2) 0.0004(18) 0.0058(18) -0.0049(18) N1 0.0132(13) 0.0178(16) 0.0126(14) 0.0004(12) 0.0051(12) -0.0014(11) N2 0.0207(16) 0.0229(18) 0.0239(17) -0.0057(15) 0.0079(14) -0.0028(14) N3 0.0182(14) 0.0344(18) 0.0184(16) 0.0008(14) 0.0089(13) -0.0002(14) O1 0.0141(12) 0.0312(14) 0.0225(12) 0.0001(11) 0.0014(10) -0.0019(11) O2 0.0211(12) 0.0345(14) 0.0130(12) -0.0024(11) 0.0005(10) -0.0045(10) O1W 0.0292(16) 0.0281(16) 0.0322(15) -0.0034(13) 0.0047(13) -0.0039(14) F1 0.0379(11) 0.0352(13) 0.0373(12) -0.0044(10) 0.0062(9) 0.0130(10) F2 0.0407(11) 0.0513(13) 0.0585(13) -0.0189(11) 0.0334(10) -0.0179(11) F3 0.0404(11) 0.0558(14) 0.0188(10) -0.0022(10) 0.0019(9) 0.0084(10) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag C1 O1 1.226(3) . ? C1 N1 1.394(3) . ? C1 C2 1.474(3) . ? C2 C3 1.369(3) . ? C2 C12 1.410(3) . ? C3 C4 1.402(3) . ? C3 H3 0.9500 . ? C4 C5 1.365(3) . ? C4 H4 0.9500 . ? C5 C6 1.414(3) . ? C5 H5 0.9500 . ? C6 C7 1.428(3) . ? C6 C12 1.432(3) . ? C7 C8 1.375(3) . ? C7 C17 1.480(3) . ? C8 C9 1.403(3) . ? C8 H8 0.9500 . ? C9 C10 1.371(3) . ? C9 H9 0.9500 . ? C10 C12 1.407(3) . ? C10 C11 1.484(3) . ? C11 O2 1.224(3) . ? C11 N1 1.401(3) . ? C13 N1 1.475(3) . ? C13 C14 1.515(3) . ? C13 H13A 0.9900 . ? C13 H13B 0.9900 . ? C14 C15 1.537(3) . ? C14 H14A 0.9900 . ? C14 H14B 0.9900 . ? C15 C16 1.516(3) . ? C15 H15A 0.9900 . ? C15 H15B 0.9900 . ? C16 H16A 0.9800 . ? C16 H16B 0.9800 . ? C16 H16C 0.9800 . ? C17 N2 1.363(3) . ? C17 C18 1.369(3) . ? C18 C19 1.388(3) . ? C18 H18 0.9500 . ? C19 N3 1.339(3) . ? C19 C20 1.472(3) . ? C20 F2 1.337(3) . ? C20 F1 1.346(3) . ? C20 F3 1.347(3) . ? N2 N3 1.358(3) . ? N2 H2N 0.93(3) . ? O1W H1WA 0.98(4) . ? O1W H1WB 0.76(4) . ? 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 O1 C1 N1 119.7(2) . . ? O1 C1 C2 122.7(3) . . ? N1 C1 C2 117.6(3) . . ? C3 C2 C12 120.6(2) . . ? C3 C2 C1 119.0(3) . . ? C12 C2 C1 120.5(3) . . ? C2 C3 C4 120.1(3) . . ? C2 C3 H3 119.9 . . ? C4 C3 H3 119.9 . . ? C5 C4 C3 120.5(3) . . ? C5 C4 H4 119.7 . . ? C3 C4 H4 119.7 . . ? C4 C5 C6 121.6(2) . . ? C4 C5 H5 119.2 . . ? C6 C5 H5 119.2 . . ? C5 C6 C7 124.7(2) . . ? C5 C6 C12 117.3(2) . . ? C7 C6 C12 117.9(2) . . ? C8 C7 C6 119.9(2) . . ? C8 C7 C17 119.8(2) . . ? C6 C7 C17 120.3(2) . . ? C7 C8 C9 121.5(3) . . ? C7 C8 H8 119.3 . . ? C9 C8 H8 119.3 . . ? C10 C9 C8 120.1(3) . . ? C10 C9 H9 119.9 . . ? C8 C9 H9 119.9 . . ? C9 C10 C12 120.4(2) . . ? C9 C10 C11 118.9(3) . . ? C12 C10 C11 120.7(2) . . ? O2 C11 N1 120.4(2) . . ? O2 C11 C10 122.8(3) . . ? N1 C11 C10 116.8(2) . . ? C10 C12 C2 120.0(2) . . ? C10 C12 C6 120.2(2) . . ? C2 C12 C6 119.8(3) . . ? N1 C13 C14 112.6(2) . . ? N1 C13 H13A 109.1 . . ? C14 C13 H13A 109.1 . . ? N1 C13 H13B 109.1 . . ? C14 C13 H13B 109.1 . . ? H13A C13 H13B 107.8 . . ? C13 C14 C15 112.2(2) . . ? C13 C14 H14A 109.2 . . ? C15 C14 H14A 109.2 . . ? C13 C14 H14B 109.2 . . ? C15 C14 H14B 109.2 . . ? H14A C14 H14B 107.9 . . ? C16 C15 C14 113.8(2) . . ? C16 C15 H15A 108.8 . . ? C14 C15 H15A 108.8 . . ? C16 C15 H15B 108.8 . . ? C14 C15 H15B 108.8 . . ? H15A C15 H15B 107.7 . . ? C15 C16 H16A 109.5 . . ? C15 C16 H16B 109.5 . . ? H16A C16 H16B 109.5 . . ? C15 C16 H16C 109.5 . . ? H16A C16 H16C 109.5 . . ? H16B C16 H16C 109.5 . . ? N2 C17 C18 106.6(2) . . ? N2 C17 C7 120.8(3) . . ? C18 C17 C7 132.5(3) . . ? C17 C18 C19 105.1(2) . . ? C17 C18 H18 127.5 . . ? C19 C18 H18 127.5 . . ? N3 C19 C18 112.6(2) . . ? N3 C19 C20 119.4(2) . . ? C18 C19 C20 128.0(3) . . ? F2 C20 F1 106.7(2) . . ? F2 C20 F3 106.8(2) . . ? F1 C20 F3 105.3(3) . . ? F2 C20 C19 113.0(3) . . ? F1 C20 C19 112.7(2) . . ? F3 C20 C19 111.8(2) . . ? C1 N1 C11 124.3(2) . . ? C1 N1 C13 118.6(2) . . ? C11 N1 C13 117.1(2) . . ? N3 N2 C17 112.2(2) . . ? N3 N2 H2N 118.8(16) . . ? C17 N2 H2N 128.7(16) . . ? C19 N3 N2 103.5(2) . . ? H1WA O1W H1WB 108(4) . . ? 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 O1 C1 C2 C3 1.0(4) . . . . ? N1 C1 C2 C3 -177.9(2) . . . . ? O1 C1 C2 C12 -179.5(3) . . . . ? N1 C1 C2 C12 1.6(4) . . . . ? C12 C2 C3 C4 0.7(4) . . . . ? C1 C2 C3 C4 -179.8(2) . . . . ? C2 C3 C4 C5 -1.0(4) . . . . ? C3 C4 C5 C6 0.1(4) . . . . ? C4 C5 C6 C7 179.7(3) . . . . ? C4 C5 C6 C12 1.0(4) . . . . ? C5 C6 C7 C8 -175.9(3) . . . . ? C12 C6 C7 C8 2.8(4) . . . . ? C5 C6 C7 C17 6.2(4) . . . . ? C12 C6 C7 C17 -175.1(2) . . . . ? C6 C7 C8 C9 -3.7(4) . . . . ? C17 C7 C8 C9 174.2(2) . . . . ? C7 C8 C9 C10 1.8(4) . . . . ? C8 C9 C10 C12 1.1(4) . . . . ? C8 C9 C10 C11 -178.5(2) . . . . ? C9 C10 C11 O2 0.4(4) . . . . ? C12 C10 C11 O2 -179.2(3) . . . . ? C9 C10 C11 N1 -179.4(2) . . . . ? C12 C10 C11 N1 1.0(4) . . . . ? C9 C10 C12 C2 178.1(2) . . . . ? C11 C10 C12 C2 -2.2(4) . . . . ? C9 C10 C12 C6 -1.9(4) . . . . ? C11 C10 C12 C6 177.7(3) . . . . ? C3 C2 C12 C10 -179.6(3) . . . . ? C1 C2 C12 C10 0.9(4) . . . . ? C3 C2 C12 C6 0.5(4) . . . . ? C1 C2 C12 C6 -179.0(2) . . . . ? C5 C6 C12 C10 178.8(3) . . . . ? C7 C6 C12 C10 0.0(4) . . . . ? C5 C6 C12 C2 -1.3(4) . . . . ? C7 C6 C12 C2 179.9(2) . . . . ? N1 C13 C14 C15 174.6(2) . . . . ? C13 C14 C15 C16 67.3(3) . . . . ? C8 C7 C17 N2 41.6(4) . . . . ? C6 C7 C17 N2 -140.5(3) . . . . ? C8 C7 C17 C18 -134.2(3) . . . . ? C6 C7 C17 C18 43.6(5) . . . . ? N2 C17 C18 C19 0.2(3) . . . . ? C7 C17 C18 C19 176.4(3) . . . . ? C17 C18 C19 N3 0.1(3) . . . . ? C17 C18 C19 C20 177.7(3) . . . . ? N3 C19 C20 F2 -2.6(4) . . . . ? C18 C19 C20 F2 180.0(3) . . . . ? N3 C19 C20 F1 -123.6(3) . . . . ? C18 C19 C20 F1 58.9(4) . . . . ? N3 C19 C20 F3 118.0(3) . . . . ? C18 C19 C20 F3 -59.5(4) . . . . ? O1 C1 N1 C11 178.1(2) . . . . ? C2 C1 N1 C11 -2.9(4) . . . . ? O1 C1 N1 C13 -1.4(4) . . . . ? C2 C1 N1 C13 177.5(2) . . . . ? O2 C11 N1 C1 -178.1(3) . . . . ? C10 C11 N1 C1 1.7(4) . . . . ? O2 C11 N1 C13 1.4(4) . . . . ? C10 C11 N1 C13 -178.8(2) . . . . ? C14 C13 N1 C1 95.0(3) . . . . ? C14 C13 N1 C11 -84.6(3) . . . . ? C18 C17 N2 N3 -0.4(3) . . . . ? C7 C17 N2 N3 -177.2(2) . . . . ? C18 C19 N3 N2 -0.4(3) . . . . ? C20 C19 N3 N2 -178.2(2) . . . . ? C17 N2 N3 C19 0.5(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 O1W H1WB O1 0.76(4) 2.35(4) 2.932(3) 134(4) . O1W H1WA N3 0.98(4) 1.96(4) 2.939(3) 174(3) 3 N2 H2N O1W 0.93(3) 1.81(3) 2.744(3) 175(3) 7_556 _diffrn_measured_fraction_theta_max 0.999 _diffrn_reflns_theta_full 24.97 _diffrn_measured_fraction_theta_full 0.999 _refine_diff_density_max 0.227 _refine_diff_density_min -0.244 _refine_diff_density_rms 0.057 _database_code_depnum_ccdc_archive 'CCDC 942177'