data_8k # local name ch108 _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C19 H19 N4 +, C2 F3 O2 -' _chemical_formula_sum 'C21 H19 F3 N4 O2' _chemical_formula_weight 416.40 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 'P 21/c' _symmetry_space_group_name_Hall '-P 2ybc' 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 13.1973(6) _cell_length_b 14.8812(7) _cell_length_c 10.1948(5) _cell_angle_alpha 90.00 _cell_angle_beta 110.978(3) _cell_angle_gamma 90.00 _cell_volume 1869.47(15) _cell_formula_units_Z 4 _cell_measurement_temperature 100(2) _cell_measurement_reflns_used 3401 _cell_measurement_theta_min 5.52 _cell_measurement_theta_max 69.54 _exptl_crystal_description block _exptl_crystal_colour colourless _exptl_crystal_size_max 0.19 _exptl_crystal_size_mid 0.17 _exptl_crystal_size_min 0.07 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.479 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 864 _exptl_absorpt_coefficient_mu 1.004 _exptl_absorpt_correction_type numerical _exptl_absorpt_correction_T_min 0.8344 _exptl_absorpt_correction_T_max 0.9330 _exptl_absorpt_process_details 'SADABS 2008/1, Sheldrick, 1996' _exptl_special_details ; ? ; _diffrn_ambient_temperature 100(2) _diffrn_radiation_wavelength 1.54178 _diffrn_radiation_type CuK\a _diffrn_radiation_source microsource _diffrn_radiation_monochromator 'silicon 111' _diffrn_measurement_device_type 'Bruker Kappa APEXII DUO CCD diffractometer' _diffrn_measurement_method '\f and \w scans' _diffrn_detector_area_resol_mean ? _diffrn_reflns_number 14493 _diffrn_reflns_av_R_equivalents 0.0391 _diffrn_reflns_av_sigmaI/netI 0.0281 _diffrn_reflns_limit_h_min -15 _diffrn_reflns_limit_h_max 15 _diffrn_reflns_limit_k_min -17 _diffrn_reflns_limit_k_max 17 _diffrn_reflns_limit_l_min -12 _diffrn_reflns_limit_l_max 8 _diffrn_reflns_theta_min 5.52 _diffrn_reflns_theta_max 66.59 _reflns_number_total 3285 _reflns_number_gt 2630 _reflns_threshold_expression I>2\s(I) _computing_data_collection 'APEX2 (Bruker, 2007)' _computing_cell_refinement 'SAINT (Bruker, 2007)' _computing_data_reduction SAINT _computing_structure_solution 'SHELXTL (Sheldrick, 2008)' _computing_structure_refinement SHELXTL _computing_molecular_graphics 'ORTEP3 for Windows (Farrugia, 1997)' _computing_publication_material 'SHELXTL and local programs' _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^)+(0.0523P)^2^+0.6815P] 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 SHELXL _refine_ls_extinction_coef 0.00090(18) _refine_ls_extinction_expression 'Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^' _refine_ls_number_reflns 3285 _refine_ls_number_parameters 348 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0498 _refine_ls_R_factor_gt 0.0368 _refine_ls_wR_factor_ref 0.1003 _refine_ls_wR_factor_gt 0.0906 _refine_ls_goodness_of_fit_ref 1.034 _refine_ls_restrained_S_all 1.034 _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 0.25980(13) 0.20902(10) 0.36272(16) 0.0225(3) Uani 1 1 d . . . H1N H 0.301(2) 0.2372(17) 0.319(2) 0.044(7) Uiso 1 1 d . . . N2 N 0.20131(12) 0.07752(10) 0.43298(15) 0.0197(3) Uani 1 1 d . . . N3 N 0.15656(12) -0.11103(10) 0.60144(15) 0.0212(3) Uani 1 1 d . . . N4 N 0.30749(12) -0.02699(10) 0.69475(15) 0.0201(3) Uani 1 1 d . . . H4N H 0.359(2) 0.0121(17) 0.700(2) 0.041(7) Uiso 1 1 d . . . C1 C 0.21650(15) -0.02196(12) 0.43381(18) 0.0214(4) Uani 1 1 d . . . C2 C 0.32299(16) -0.02977(13) 0.40448(19) 0.0250(4) Uani 1 1 d . . . H2A H 0.3217(17) -0.0827(15) 0.348(2) 0.028(5) Uiso 1 1 d . . . H2B H 0.3874(18) -0.0336(14) 0.494(2) 0.027(5) Uiso 1 1 d . . . C3 C 0.33090(16) 0.05817(13) 0.32941(19) 0.0239(4) Uani 1 1 d . . . H3A H 0.4043(19) 0.0811(15) 0.355(2) 0.031(6) Uiso 1 1 d . . . H3B H 0.2979(17) 0.0551(14) 0.226(2) 0.027(5) Uiso 1 1 d . . . C4 C 0.26201(14) 0.12103(12) 0.37616(17) 0.0206(4) Uani 1 1 d . . . C5 C 0.19152(14) 0.26216(12) 0.41139(18) 0.0211(4) Uani 1 1 d . . . C6 C 0.19493(16) 0.35508(13) 0.40237(19) 0.0246(4) Uani 1 1 d . . . H6 H 0.2455(17) 0.3826(15) 0.363(2) 0.030(6) Uiso 1 1 d . . . C7 C 0.13017(16) 0.40715(13) 0.4534(2) 0.0257(4) Uani 1 1 d . . . H7 H 0.1350(17) 0.4706(15) 0.449(2) 0.027(5) Uiso 1 1 d . . . C8 C 0.06186(15) 0.36643(13) 0.5125(2) 0.0254(4) Uani 1 1 d . . . H8 H 0.0175(18) 0.4009(15) 0.549(2) 0.033(6) Uiso 1 1 d . . . C9 C 0.05871(15) 0.27317(13) 0.52024(19) 0.0239(4) Uani 1 1 d . . . H9 H 0.0105(17) 0.2422(14) 0.564(2) 0.028(5) Uiso 1 1 d . . . C10 C 0.12347(14) 0.22023(12) 0.47048(18) 0.0208(4) Uani 1 1 d . . . C11 C 0.12161(16) 0.11921(13) 0.4837(2) 0.0255(4) Uani 1 1 d . . . H11A H 0.1410(16) 0.1014(13) 0.585(2) 0.021(5) Uiso 1 1 d . . . H11B H 0.0504(19) 0.0966(16) 0.429(2) 0.038(6) Uiso 1 1 d . . . C12 C 0.12039(18) -0.06480(14) 0.3182(2) 0.0298(5) Uani 1 1 d . . . H12A H 0.0508(18) -0.0494(15) 0.330(2) 0.029(6) Uiso 1 1 d . . . H12B H 0.1332(17) -0.1308(15) 0.318(2) 0.027(5) Uiso 1 1 d . . . H12C H 0.1162(18) -0.0405(16) 0.226(2) 0.039(6) Uiso 1 1 d . . . C13 C 0.22574(14) -0.05625(11) 0.57670(18) 0.0186(4) Uani 1 1 d . . . C14 C 0.19581(14) -0.11980(12) 0.74718(18) 0.0203(4) Uani 1 1 d . . . C15 C 0.15625(16) -0.17100(12) 0.8330(2) 0.0245(4) Uani 1 1 d . . . H15 H 0.0896(18) -0.2077(15) 0.789(2) 0.029(6) Uiso 1 1 d . . . C16 C 0.21213(16) -0.16770(13) 0.9767(2) 0.0262(4) Uani 1 1 d . . . H16 H 0.1857(18) -0.2035(15) 1.039(2) 0.035(6) Uiso 1 1 d . . . C17 C 0.30492(16) -0.11353(13) 1.03471(19) 0.0252(4) Uani 1 1 d . . . H17 H 0.3407(17) -0.1111(15) 1.135(2) 0.029(6) Uiso 1 1 d . . . C18 C 0.34562(15) -0.06232(13) 0.95171(19) 0.0236(4) Uani 1 1 d . . . H18 H 0.4116(18) -0.0261(15) 0.993(2) 0.031(6) Uiso 1 1 d . . . C19 C 0.29002(14) -0.06695(11) 0.80685(18) 0.0203(4) Uani 1 1 d . . . F1 F 0.44723(10) 0.18366(8) 0.10259(15) 0.0453(4) Uani 1 1 d . . . F2 F 0.59257(10) 0.26390(8) 0.16441(15) 0.0398(3) Uani 1 1 d . . . F3 F 0.54035(11) 0.20423(9) 0.32068(14) 0.0432(3) Uani 1 1 d . . . O1 O 0.35241(11) 0.31176(9) 0.22310(14) 0.0297(3) Uani 1 1 d . . . O2 O 0.46713(10) 0.40267(9) 0.17004(14) 0.0260(3) Uani 1 1 d . . . C20 C 0.43547(14) 0.32867(12) 0.19637(18) 0.0220(4) Uani 1 1 d . . . C21 C 0.50494(15) 0.24497(13) 0.1947(2) 0.0266(4) 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 0.0242(8) 0.0201(8) 0.0264(8) 0.0027(6) 0.0130(7) -0.0002(6) N2 0.0208(7) 0.0180(7) 0.0207(7) 0.0008(6) 0.0081(6) 0.0000(6) N3 0.0231(8) 0.0169(7) 0.0244(8) 0.0004(6) 0.0096(6) -0.0010(6) N4 0.0216(8) 0.0176(7) 0.0222(7) 0.0005(6) 0.0090(6) -0.0013(6) C1 0.0264(10) 0.0168(9) 0.0215(9) -0.0005(7) 0.0092(8) -0.0011(7) C2 0.0324(10) 0.0220(9) 0.0252(9) -0.0004(7) 0.0159(8) 0.0045(8) C3 0.0284(10) 0.0232(9) 0.0237(9) 0.0011(7) 0.0137(8) 0.0020(8) C4 0.0212(9) 0.0222(9) 0.0180(8) 0.0017(7) 0.0067(7) -0.0009(7) C5 0.0183(9) 0.0208(9) 0.0223(8) 0.0006(7) 0.0049(7) 0.0020(7) C6 0.0236(9) 0.0222(9) 0.0261(9) 0.0029(7) 0.0067(8) -0.0019(8) C7 0.0252(10) 0.0179(9) 0.0313(10) -0.0009(7) 0.0069(8) 0.0017(8) C8 0.0205(9) 0.0252(10) 0.0291(9) -0.0023(7) 0.0070(8) 0.0044(8) C9 0.0213(9) 0.0260(10) 0.0243(9) 0.0001(7) 0.0083(8) 0.0010(8) C10 0.0185(9) 0.0206(9) 0.0213(8) 0.0011(6) 0.0049(7) 0.0005(7) C11 0.0236(10) 0.0219(10) 0.0351(10) 0.0034(8) 0.0156(8) 0.0010(8) C12 0.0398(12) 0.0241(10) 0.0228(10) -0.0010(7) 0.0080(9) -0.0083(9) C13 0.0201(9) 0.0154(8) 0.0221(8) -0.0001(6) 0.0097(7) 0.0015(7) C14 0.0216(9) 0.0167(8) 0.0240(8) 0.0003(7) 0.0098(7) 0.0035(7) C15 0.0246(10) 0.0194(9) 0.0308(10) 0.0029(7) 0.0114(8) -0.0003(8) C16 0.0305(10) 0.0231(10) 0.0288(10) 0.0071(7) 0.0153(8) 0.0035(8) C17 0.0275(10) 0.0256(10) 0.0233(9) 0.0022(7) 0.0100(8) 0.0067(8) C18 0.0226(9) 0.0228(9) 0.0251(9) -0.0009(7) 0.0080(8) 0.0028(8) C19 0.0212(9) 0.0163(8) 0.0253(9) 0.0002(7) 0.0106(7) 0.0025(7) F1 0.0355(7) 0.0301(7) 0.0615(9) -0.0186(6) 0.0064(6) -0.0006(6) F2 0.0342(7) 0.0266(6) 0.0690(9) -0.0044(6) 0.0312(6) 0.0020(5) F3 0.0438(7) 0.0345(7) 0.0474(7) 0.0151(6) 0.0117(6) 0.0133(6) O1 0.0270(7) 0.0277(7) 0.0405(8) 0.0095(6) 0.0196(6) 0.0031(6) O2 0.0254(7) 0.0211(7) 0.0348(7) 0.0030(5) 0.0148(6) 0.0012(5) C20 0.0217(9) 0.0230(9) 0.0212(8) 0.0015(7) 0.0076(7) 0.0003(8) C21 0.0235(9) 0.0218(9) 0.0353(10) 0.0002(8) 0.0115(8) -0.0024(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 H1N 0.92(3) . ? N1 C4 1.316(2) . ? N1 C5 1.415(2) . ? N2 C1 1.493(2) . ? N2 C4 1.315(2) . ? N2 C11 1.465(2) . ? N3 C13 1.314(2) . ? N3 C14 1.393(2) . ? N4 H4N 0.89(3) . ? N4 C13 1.368(2) . ? N4 C19 1.379(2) . ? C1 C2 1.542(3) . ? C1 C12 1.528(3) . ? C1 C13 1.507(2) . ? C2 H2A 0.97(2) . ? C2 H2B 1.00(2) . ? C2 C3 1.538(2) . ? C3 H3A 0.97(2) . ? C3 H3B 0.99(2) . ? C3 C4 1.496(2) . ? C5 C6 1.388(3) . ? C5 C10 1.395(3) . ? C6 H6 0.98(2) . ? C6 C7 1.386(3) . ? C7 H7 0.95(2) . ? C7 C8 1.390(3) . ? C8 H8 0.95(2) . ? C8 C9 1.391(3) . ? C9 H9 1.01(2) . ? C9 C10 1.385(3) . ? C10 C11 1.510(2) . ? C11 H11A 1.00(2) . ? C11 H11B 0.97(2) . ? C12 H12A 0.99(2) . ? C12 H12B 1.00(2) . ? C12 H12C 0.99(2) . ? C14 C15 1.395(3) . ? C14 C19 1.412(2) . ? C15 H15 1.00(2) . ? C15 C16 1.385(3) . ? C16 H16 0.98(2) . ? C16 C17 1.407(3) . ? C17 H17 0.96(2) . ? C17 C18 1.382(3) . ? C18 H18 0.98(2) . ? C18 C19 1.396(2) . ? F1 C21 1.335(2) . ? F2 C21 1.329(2) . ? F3 C21 1.344(2) . ? O1 C20 1.246(2) . ? O2 C20 1.241(2) . ? C20 C21 1.550(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 H1N N1 C4 120.5(16) . . ? H1N N1 C5 118.6(16) . . ? C4 N1 C5 120.84(16) . . ? C1 N2 C4 112.88(15) . . ? C1 N2 C11 121.98(14) . . ? C4 N2 C11 125.05(15) . . ? C13 N3 C14 104.14(14) . . ? H4N N4 C13 127.4(15) . . ? H4N N4 C19 126.3(15) . . ? C13 N4 C19 106.18(15) . . ? N2 C1 C2 101.74(14) . . ? N2 C1 C12 109.67(15) . . ? N2 C1 C13 107.78(14) . . ? C2 C1 C12 112.42(15) . . ? C2 C1 C13 113.45(15) . . ? C12 C1 C13 111.22(15) . . ? C1 C2 H2A 110.7(13) . . ? C1 C2 H2B 111.3(12) . . ? C1 C2 C3 105.14(15) . . ? H2A C2 H2B 108.9(17) . . ? H2A C2 C3 112.5(13) . . ? H2B C2 C3 108.4(12) . . ? C2 C3 H3A 113.9(13) . . ? C2 C3 H3B 114.1(12) . . ? C2 C3 C4 102.48(14) . . ? H3A C3 H3B 108.7(18) . . ? H3A C3 C4 110.9(13) . . ? H3B C3 C4 106.4(12) . . ? N1 C4 N2 122.80(17) . . ? N1 C4 C3 125.61(16) . . ? N2 C4 C3 111.59(16) . . ? N1 C5 C6 119.59(17) . . ? N1 C5 C10 119.37(16) . . ? C6 C5 C10 121.03(17) . . ? C5 C6 H6 119.0(13) . . ? C5 C6 C7 119.55(18) . . ? H6 C6 C7 121.4(13) . . ? C6 C7 H7 118.4(13) . . ? C6 C7 C8 120.14(18) . . ? H7 C7 C8 121.5(13) . . ? C7 C8 H8 121.4(14) . . ? C7 C8 C9 119.78(18) . . ? H8 C8 C9 118.8(14) . . ? C8 C9 H9 121.1(12) . . ? C8 C9 C10 120.77(18) . . ? H9 C9 C10 118.2(12) . . ? C5 C10 C9 118.74(17) . . ? C5 C10 C11 121.14(16) . . ? C9 C10 C11 120.11(16) . . ? N2 C11 C10 110.70(15) . . ? N2 C11 H11A 107.4(11) . . ? N2 C11 H11B 108.8(14) . . ? C10 C11 H11A 110.4(11) . . ? C10 C11 H11B 109.8(14) . . ? H11A C11 H11B 109.9(18) . . ? C1 C12 H12A 111.1(12) . . ? C1 C12 H12B 108.5(12) . . ? C1 C12 H12C 109.2(13) . . ? H12A C12 H12B 113.1(18) . . ? H12A C12 H12C 106.7(18) . . ? H12B C12 H12C 108.2(18) . . ? N3 C13 N4 114.32(15) . . ? N3 C13 C1 125.06(16) . . ? N4 C13 C1 120.53(15) . . ? N3 C14 C15 129.82(17) . . ? N3 C14 C19 109.95(15) . . ? C15 C14 C19 120.23(16) . . ? C14 C15 H15 119.2(12) . . ? C14 C15 C16 117.84(17) . . ? H15 C15 C16 123.0(12) . . ? C15 C16 H16 118.9(13) . . ? C15 C16 C17 121.22(17) . . ? H16 C16 C17 119.8(13) . . ? C16 C17 H17 119.3(13) . . ? C16 C17 C18 121.93(17) . . ? H17 C17 C18 118.8(13) . . ? C17 C18 H18 121.5(13) . . ? C17 C18 C19 116.63(18) . . ? H18 C18 C19 121.9(13) . . ? N4 C19 C14 105.42(15) . . ? N4 C19 C18 132.46(17) . . ? C14 C19 C18 122.12(17) . . ? O1 C20 O2 128.11(18) . . ? O1 C20 C21 114.23(16) . . ? O2 C20 C21 117.66(16) . . ? F1 C21 F2 107.85(16) . . ? F1 C21 F3 106.23(16) . . ? F1 C21 C20 111.48(15) . . ? F2 C21 F3 106.48(16) . . ? F2 C21 C20 113.54(15) . . ? F3 C21 C20 110.86(16) . . ? 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 C4 N2 C1 C2 15.66(18) . . . . ? C4 N2 C1 C12 -103.55(17) . . . . ? C4 N2 C1 C13 135.23(15) . . . . ? C11 N2 C1 C2 -167.67(15) . . . . ? C11 N2 C1 C12 73.1(2) . . . . ? C11 N2 C1 C13 -48.1(2) . . . . ? N2 C1 C2 C3 -23.57(17) . . . . ? C12 C1 C2 C3 93.66(18) . . . . ? C13 C1 C2 C3 -139.05(15) . . . . ? C1 C2 C3 C4 23.39(18) . . . . ? C1 N2 C4 N1 178.82(16) . . . . ? C1 N2 C4 C3 -0.7(2) . . . . ? C11 N2 C4 N1 2.3(3) . . . . ? C11 N2 C4 C3 -177.24(16) . . . . ? C5 N1 C4 N2 0.8(3) . . . . ? C5 N1 C4 C3 -179.76(16) . . . . ? C2 C3 C4 N1 165.83(17) . . . . ? C2 C3 C4 N2 -14.7(2) . . . . ? C4 N1 C5 C6 176.71(17) . . . . ? C4 N1 C5 C10 -1.9(3) . . . . ? N1 C5 C6 C7 -178.29(16) . . . . ? C10 C5 C6 C7 0.3(3) . . . . ? C5 C6 C7 C8 -0.4(3) . . . . ? C6 C7 C8 C9 0.0(3) . . . . ? C7 C8 C9 C10 0.4(3) . . . . ? C8 C9 C10 C5 -0.5(3) . . . . ? C8 C9 C10 C11 178.14(17) . . . . ? N1 C5 C10 C9 178.71(16) . . . . ? N1 C5 C10 C11 0.1(3) . . . . ? C6 C5 C10 C9 0.1(3) . . . . ? C6 C5 C10 C11 -178.48(17) . . . . ? C1 N2 C11 C10 -179.90(14) . . . . ? C4 N2 C11 C10 -3.7(2) . . . . ? C5 C10 C11 N2 2.4(2) . . . . ? C9 C10 C11 N2 -176.20(16) . . . . ? C14 N3 C13 N4 -0.67(19) . . . . ? C14 N3 C13 C1 -177.21(16) . . . . ? C19 N4 C13 N3 0.3(2) . . . . ? C19 N4 C13 C1 177.02(15) . . . . ? N2 C1 C13 N3 115.82(18) . . . . ? N2 C1 C13 N4 -60.5(2) . . . . ? C2 C1 C13 N3 -132.35(18) . . . . ? C2 C1 C13 N4 51.3(2) . . . . ? C12 C1 C13 N3 -4.4(2) . . . . ? C12 C1 C13 N4 179.23(16) . . . . ? C13 N3 C14 C15 -178.76(18) . . . . ? C13 N3 C14 C19 0.77(19) . . . . ? N3 C14 C15 C16 179.63(18) . . . . ? C19 C14 C15 C16 0.1(3) . . . . ? C14 C15 C16 C17 0.9(3) . . . . ? C15 C16 C17 C18 -1.0(3) . . . . ? C16 C17 C18 C19 0.0(3) . . . . ? C13 N4 C19 C14 0.19(18) . . . . ? C13 N4 C19 C18 -179.63(19) . . . . ? C17 C18 C19 N4 -179.12(18) . . . . ? C17 C18 C19 C14 1.1(3) . . . . ? N3 C14 C19 N4 -0.60(19) . . . . ? N3 C14 C19 C18 179.25(16) . . . . ? C15 C14 C19 N4 178.98(16) . . . . ? C15 C14 C19 C18 -1.2(3) . . . . ? O1 C20 C21 F1 57.2(2) . . . . ? O1 C20 C21 F2 179.26(16) . . . . ? O1 C20 C21 F3 -60.9(2) . . . . ? O2 C20 C21 F1 -121.94(18) . . . . ? O2 C20 C21 F2 0.1(2) . . . . ? O2 C20 C21 F3 119.93(18) . . . . ? 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 N1 H1N O1 0.92(3) 1.76(3) 2.665(2) 165(2) . N4 H4N O2 0.89(3) 2.01(3) 2.882(2) 169(2) 4_566 _diffrn_measured_fraction_theta_max 0.995 _diffrn_reflns_theta_full 66.59 _diffrn_measured_fraction_theta_full 0.995 _refine_diff_density_max 0.240 _refine_diff_density_min -0.213 _refine_diff_density_rms 0.046