data_d4003 _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety '3(C4 H3 F N2 O2), C6 H6 N2 O, H2 O' _chemical_formula_sum 'C18 H17 F3 N8 O8' _chemical_formula_weight 530.40 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source 'C' 'C' 0.0033 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 'triclinic' _symmetry_space_group_name_H-M 'P -1' _symmetry_space_group_name_Hall '-P 1' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 8.1842(8) _cell_length_b 11.5004(15) _cell_length_c 12.7610(13) _cell_angle_alpha 86.296(9) _cell_angle_beta 76.709(8) _cell_angle_gamma 69.343(10) _cell_volume 1093.6(2) _cell_formula_units_Z 2 _cell_measurement_temperature 295(2) _cell_measurement_reflns_used 1372 _cell_measurement_theta_min 3.46 _cell_measurement_theta_max 27.56 _exptl_crystal_description prism _exptl_crystal_colour colorless _exptl_crystal_size_max 0.26 _exptl_crystal_size_mid 0.12 _exptl_crystal_size_min 0.10 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.611 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 544 _exptl_absorpt_coefficient_mu 0.144 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.9635 _exptl_absorpt_correction_T_max 0.9857 _exptl_absorpt_process_details ; CrysAlis Pro (Agilent, 2013) Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm. ; _diffrn_ambient_temperature 295(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'Enhance (Mo) X-ray Source' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Xcalibur, Eos' _diffrn_measurement_method '\w scans' _diffrn_detector_area_resol_mean 16.1954 _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 6492 _diffrn_reflns_av_R_equivalents 0.0144 _diffrn_reflns_av_sigmaI/netI 0.0427 _diffrn_reflns_limit_h_min -10 _diffrn_reflns_limit_h_max 8 _diffrn_reflns_limit_k_min -14 _diffrn_reflns_limit_k_max 14 _diffrn_reflns_limit_l_min -16 _diffrn_reflns_limit_l_max 16 _diffrn_reflns_theta_min 3.28 _diffrn_reflns_theta_max 27.56 _reflns_number_total 4980 _reflns_number_gt 3250 _reflns_threshold_expression >2sigma(I) _computing_data_collection ; CrysAlis Pro (Agilent, 2013) ; _computing_cell_refinement ; CrysAlis Pro (Agilent, 2013) ; _computing_data_reduction ; CrysAlis Pro (Agilent, 2013) ; _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics '(K. Brandenburg, Diamond 3.1, 2009)' _computing_publication_material '(K. Brandenburg, Diamond 3.1, 2009)' _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^)+(0.0553P)^2^+0.0391P] 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 0.0041(10) _refine_ls_extinction_expression 'Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^' _refine_ls_number_reflns 4980 _refine_ls_number_parameters 365 _refine_ls_number_restraints 11 _refine_ls_R_factor_all 0.0782 _refine_ls_R_factor_gt 0.0467 _refine_ls_wR_factor_ref 0.1306 _refine_ls_wR_factor_gt 0.1072 _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 F1 F -0.00430(17) 0.31503(13) 0.30435(10) 0.0682(4) Uani 1 1 d . . . F2 F 0.29387(17) 0.46354(12) 0.79324(10) 0.0600(4) Uani 1 1 d . . . F3 F -0.09027(17) 0.40578(12) 0.99485(10) 0.0672(4) Uani 1 1 d . . . O1 O 0.8967(2) 0.07384(14) 0.13031(12) 0.0597(5) Uani 1 1 d . . . O2 O 0.7636(2) 0.15479(14) 0.48044(12) 0.0599(4) Uani 1 1 d . . . O3 O 0.35581(18) 0.09972(13) 0.60651(11) 0.0479(4) Uani 1 1 d . . . O4 O -0.11988(18) 0.40233(13) 0.51431(12) 0.0529(4) Uani 1 1 d . . . O5 O 0.01437(19) 0.31994(13) 0.78370(11) 0.0516(4) Uani 1 1 d . . . O6 O 0.48924(19) 0.00427(13) 0.86187(12) 0.0515(4) Uani 1 1 d . . . O7 O 0.5797(2) 0.26877(14) 0.83474(11) 0.0571(4) Uani 1 1 d . . . O1W O 1.0171(2) -0.01774(15) 0.31875(14) 0.0677(5) Uani 1 1 d D . . N1 N 0.8007(2) 0.13109(17) -0.02164(13) 0.0491(5) Uani 1 1 d D . . N2 N 0.4793(2) 0.34840(15) 0.31473(13) 0.0438(4) Uani 1 1 d . . . N3 N 0.3280(2) 0.10809(15) 0.43333(13) 0.0419(4) Uani 1 1 d D . . N4 N 0.1187(2) 0.25042(14) 0.55856(13) 0.0396(4) Uani 1 1 d D . . N5 N 0.5142(2) 0.32489(16) 0.53192(13) 0.0420(4) Uani 1 1 d D . . N6 N 0.6711(2) 0.21411(15) 0.65706(14) 0.0414(4) Uani 1 1 d D . . N7 N 0.2522(2) 0.16327(15) 0.82555(13) 0.0418(4) Uani 1 1 d D . . N8 N 0.3040(2) 0.13921(16) 0.99666(14) 0.0464(4) Uani 1 1 d . . . C1 C 0.7857(3) 0.14523(18) 0.08214(15) 0.0402(5) Uani 1 1 d . . . C2 C 0.6313(2) 0.25047(16) 0.14215(15) 0.0355(4) Uani 1 1 d . . . C3 C 0.5060(3) 0.33869(18) 0.09469(17) 0.0467(5) Uani 1 1 d . . . H3A H 0.5147 0.3364 0.0208 0.056 Uiso 1 1 calc R . . C4 C 0.3685(3) 0.42971(19) 0.15897(17) 0.0511(6) Uani 1 1 d . . . H4A H 0.2827 0.4898 0.1290 0.061 Uiso 1 1 calc R . . C5 C 0.3588(3) 0.43125(18) 0.26743(16) 0.0445(5) Uani 1 1 d . . . H5A H 0.2641 0.4927 0.3100 0.053 Uiso 1 1 calc R . . C6 C 0.6128(3) 0.25991(18) 0.25183(15) 0.0417(5) Uani 1 1 d . . . H6A H 0.6977 0.2016 0.2838 0.050 Uiso 1 1 calc R . . C7 C 0.0160(2) 0.31321(17) 0.48632(16) 0.0388(5) Uani 1 1 d . . . C8 C 0.0885(3) 0.26036(19) 0.37874(15) 0.0426(5) Uani 1 1 d . . . C9 C 0.2374(3) 0.16162(19) 0.35527(16) 0.0444(5) Uani 1 1 d . . . H9A H 0.2800 0.1289 0.2854 0.053 Uiso 1 1 calc R . . C10 C 0.2730(2) 0.14917(17) 0.53625(15) 0.0370(4) Uani 1 1 d . . . C11 C 0.3934(3) 0.40385(17) 0.61214(16) 0.0401(5) Uani 1 1 d . . . H11A H 0.2980 0.4697 0.5956 0.048 Uiso 1 1 calc R . . C12 C 0.4111(3) 0.38735(18) 0.71272(16) 0.0395(5) Uani 1 1 d . . . C13 C 0.5569(3) 0.28819(18) 0.74292(15) 0.0392(5) Uani 1 1 d . . . C14 C 0.6569(3) 0.22669(18) 0.55153(16) 0.0403(5) Uani 1 1 d . . . C15 C 0.3563(3) 0.09705(18) 0.89346(16) 0.0406(5) Uani 1 1 d . . . C16 C 0.1548(3) 0.24331(19) 1.03063(17) 0.0475(5) Uani 1 1 d . . . H16A H 0.1229 0.2699 1.1022 0.057 Uiso 1 1 calc R . . C17 C 0.0571(3) 0.30546(19) 0.96274(17) 0.0450(5) Uani 1 1 d . . . C18 C 0.0991(3) 0.26827(18) 0.85129(16) 0.0398(5) Uani 1 1 d . . . H5N H 0.498(3) 0.334(2) 0.4663(10) 0.060 Uiso 1 1 d D . . H1N1 H 0.889(2) 0.0706(13) -0.0571(15) 0.060 Uiso 1 1 d D . . H4N H 0.082(3) 0.275(2) 0.6254(9) 0.060 Uiso 1 1 d D . . H1N2 H 0.738(2) 0.1765(16) -0.0634(14) 0.060 Uiso 1 1 d D . . H3N H 0.4253(19) 0.0458(14) 0.4166(18) 0.060 Uiso 1 1 d D . . H6N H 0.763(2) 0.1524(15) 0.6674(19) 0.060 Uiso 1 1 d D . . H8N H 0.362(3) 0.096(2) 1.0481(19) 0.060 Uiso 1 1 d . . . H1W1 H 0.977(3) 0.0127(18) 0.2624(10) 0.060 Uiso 1 1 d D . . H1W2 H 0.950(3) 0.0311(16) 0.3720(11) 0.060 Uiso 1 1 d D . . H7N H 0.282(3) 0.139(2) 0.7576(9) 0.060 Uiso 1 1 d 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 F1 0.0565(8) 0.0838(10) 0.0383(7) -0.0009(7) -0.0223(6) 0.0147(7) F2 0.0545(8) 0.0618(8) 0.0419(7) -0.0162(6) -0.0022(6) 0.0041(6) F3 0.0537(8) 0.0672(8) 0.0495(8) -0.0169(7) -0.0126(6) 0.0206(6) O1 0.0538(9) 0.0584(9) 0.0369(8) -0.0043(7) -0.0176(7) 0.0223(7) O2 0.0547(9) 0.0616(10) 0.0411(9) -0.0128(8) -0.0045(7) 0.0053(7) O3 0.0412(8) 0.0495(8) 0.0350(8) -0.0032(6) -0.0142(6) 0.0101(6) O4 0.0402(8) 0.0520(8) 0.0441(9) -0.0063(7) -0.0130(7) 0.0145(6) O5 0.0449(8) 0.0561(9) 0.0357(8) -0.0033(7) -0.0155(7) 0.0089(7) O6 0.0489(8) 0.0467(8) 0.0395(8) -0.0019(7) -0.0128(7) 0.0094(7) O7 0.0647(10) 0.0667(10) 0.0331(8) 0.0037(7) -0.0226(8) -0.0079(8) O1W 0.0611(11) 0.0638(11) 0.0499(10) -0.0104(9) -0.0231(9) 0.0212(8) N1 0.0462(10) 0.0487(10) 0.0310(9) -0.0079(8) -0.0120(8) 0.0129(8) N2 0.0455(10) 0.0433(9) 0.0318(9) -0.0057(7) -0.0111(8) 0.0002(7) N3 0.0355(9) 0.0412(9) 0.0326(9) -0.0065(7) -0.0067(7) 0.0074(7) N4 0.0341(9) 0.0404(9) 0.0307(9) -0.0052(7) -0.0102(7) 0.0064(7) N5 0.0414(9) 0.0471(10) 0.0292(9) 0.0015(8) -0.0116(8) -0.0032(8) N6 0.0376(9) 0.0409(9) 0.0357(9) 0.0023(7) -0.0134(8) 0.0016(7) N7 0.0413(9) 0.0429(9) 0.0282(8) -0.0048(7) -0.0099(8) 0.0033(7) N8 0.0474(10) 0.0479(10) 0.0310(9) 0.0008(8) -0.0131(8) 0.0020(8) C1 0.0380(10) 0.0393(10) 0.0316(10) -0.0019(8) -0.0098(9) 0.0022(8) C2 0.0343(10) 0.0341(9) 0.0303(10) -0.0032(8) -0.0096(8) 0.0000(8) C3 0.0479(12) 0.0460(11) 0.0318(11) -0.0051(9) -0.0153(9) 0.0059(9) C4 0.0479(12) 0.0458(12) 0.0425(12) -0.0049(10) -0.0203(10) 0.0119(9) C5 0.0397(11) 0.0409(11) 0.0384(11) -0.0092(9) -0.0078(9) 0.0048(8) C6 0.0386(11) 0.0415(11) 0.0351(11) -0.0012(9) -0.0137(9) 0.0020(8) C7 0.0309(10) 0.0399(10) 0.0371(11) 0.0008(9) -0.0113(8) 0.0002(8) C8 0.0363(10) 0.0503(12) 0.0317(10) 0.0027(9) -0.0140(9) 0.0002(9) C9 0.0403(11) 0.0512(12) 0.0309(10) -0.0052(9) -0.0103(9) -0.0003(9) C10 0.0323(10) 0.0364(10) 0.0330(10) -0.0011(8) -0.0083(8) 0.0002(8) C11 0.0361(10) 0.0395(10) 0.0379(11) 0.0021(9) -0.0124(9) -0.0027(8) C12 0.0370(10) 0.0409(10) 0.0307(10) -0.0048(8) -0.0058(8) -0.0016(8) C13 0.0413(11) 0.0439(11) 0.0290(10) 0.0011(8) -0.0110(9) -0.0089(9) C14 0.0374(10) 0.0433(11) 0.0321(11) 0.0016(9) -0.0081(9) -0.0041(9) C15 0.0388(11) 0.0413(11) 0.0340(11) 0.0039(9) -0.0119(9) -0.0028(9) C16 0.0464(12) 0.0512(12) 0.0329(11) -0.0047(10) -0.0087(10) -0.0016(10) C17 0.0386(11) 0.0445(11) 0.0375(11) -0.0064(9) -0.0086(9) 0.0043(9) C18 0.0342(10) 0.0423(11) 0.0344(11) -0.0012(9) -0.0088(9) -0.0019(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 F1 C8 1.338(2) . ? F2 C12 1.347(2) . ? F3 C17 1.344(2) . ? O1 C1 1.242(2) . ? O2 C14 1.222(2) . ? O3 C10 1.236(2) . ? O4 C7 1.215(2) . ? O5 C18 1.223(2) . ? O6 C15 1.233(2) . ? O7 C13 1.223(2) . ? O1W H1W1 0.861(9) . ? O1W H1W2 0.859(9) . ? N1 C1 1.317(2) . ? N1 H1N1 0.862(9) . ? N1 H1N2 0.849(9) . ? N2 C5 1.335(3) . ? N2 C6 1.338(2) . ? N3 C10 1.345(2) . ? N3 C9 1.363(3) . ? N3 H3N 0.856(9) . ? N4 C10 1.368(2) . ? N4 C7 1.385(2) . ? N4 H4N 0.867(10) . ? N5 C14 1.367(2) . ? N5 C11 1.368(2) . ? N5 H5N 0.871(10) . ? N6 C14 1.372(2) . ? N6 C13 1.374(2) . ? N6 H6N 0.863(10) . ? N7 C15 1.362(3) . ? N7 C18 1.389(2) . ? N7 H7N 0.882(9) . ? N8 C15 1.353(3) . ? N8 C16 1.380(3) . ? N8 H8N 0.92(2) . ? C1 C2 1.498(2) . ? C2 C6 1.380(3) . ? C2 C3 1.385(3) . ? C3 C4 1.375(3) . ? C3 H3A 0.9300 . ? C4 C5 1.369(3) . ? C4 H4A 0.9300 . ? C5 H5A 0.9300 . ? C6 H6A 0.9300 . ? C7 C8 1.444(3) . ? C8 C9 1.328(3) . ? C9 H9A 0.9300 . ? C11 C12 1.319(3) . ? C11 H11A 0.9300 . ? C12 C13 1.438(3) . ? C16 C17 1.318(3) . ? C16 H16A 0.9300 . ? C17 C18 1.440(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 H1W1 O1W H1W2 107.1(13) . . ? C1 N1 H1N1 119.6(13) . . ? C1 N1 H1N2 129.6(13) . . ? H1N1 N1 H1N2 110.7(13) . . ? C5 N2 C6 117.34(16) . . ? C10 N3 C9 123.19(16) . . ? C10 N3 H3N 117.8(16) . . ? C9 N3 H3N 119.1(16) . . ? C10 N4 C7 126.57(16) . . ? C10 N4 H4N 115.1(16) . . ? C7 N4 H4N 118.3(16) . . ? C14 N5 C11 122.25(17) . . ? C14 N5 H5N 117.9(16) . . ? C11 N5 H5N 119.7(16) . . ? C14 N6 C13 126.79(16) . . ? C14 N6 H6N 113.6(16) . . ? C13 N6 H6N 119.6(16) . . ? C15 N7 C18 126.94(17) . . ? C15 N7 H7N 118.5(15) . . ? C18 N7 H7N 114.5(15) . . ? C15 N8 C16 121.96(18) . . ? C15 N8 H8N 120.9(14) . . ? C16 N8 H8N 117.0(14) . . ? O1 C1 N1 121.38(18) . . ? O1 C1 C2 119.93(17) . . ? N1 C1 C2 118.69(17) . . ? C6 C2 C3 117.98(17) . . ? C6 C2 C1 117.77(16) . . ? C3 C2 C1 124.25(17) . . ? C4 C3 C2 118.66(18) . . ? C4 C3 H3A 120.7 . . ? C2 C3 H3A 120.7 . . ? C5 C4 C3 119.56(18) . . ? C5 C4 H4A 120.2 . . ? C3 C4 H4A 120.2 . . ? N2 C5 C4 122.86(18) . . ? N2 C5 H5A 118.6 . . ? C4 C5 H5A 118.6 . . ? N2 C6 C2 123.58(18) . . ? N2 C6 H6A 118.2 . . ? C2 C6 H6A 118.2 . . ? O4 C7 N4 121.56(18) . . ? O4 C7 C8 125.77(18) . . ? N4 C7 C8 112.67(16) . . ? C9 C8 F1 121.81(18) . . ? C9 C8 C7 121.86(18) . . ? F1 C8 C7 116.31(16) . . ? C8 C9 N3 120.14(18) . . ? C8 C9 H9A 119.9 . . ? N3 C9 H9A 119.9 . . ? O3 C10 N3 122.68(17) . . ? O3 C10 N4 121.75(17) . . ? N3 C10 N4 115.57(17) . . ? C12 C11 N5 120.52(17) . . ? C12 C11 H11A 119.7 . . ? N5 C11 H11A 119.7 . . ? C11 C12 F2 121.73(17) . . ? C11 C12 C13 122.23(17) . . ? F2 C12 C13 116.04(17) . . ? O7 C13 N6 122.08(18) . . ? O7 C13 C12 124.91(18) . . ? N6 C13 C12 113.01(17) . . ? O2 C14 N5 122.51(18) . . ? O2 C14 N6 122.31(18) . . ? N5 C14 N6 115.19(17) . . ? O6 C15 N8 122.72(18) . . ? O6 C15 N7 121.44(18) . . ? N8 C15 N7 115.84(17) . . ? C17 C16 N8 120.66(19) . . ? C17 C16 H16A 119.7 . . ? N8 C16 H16A 119.7 . . ? C16 C17 F3 121.44(18) . . ? C16 C17 C18 122.15(18) . . ? F3 C17 C18 116.39(18) . . ? O5 C18 N7 121.44(18) . . ? O5 C18 C17 126.13(18) . . ? N7 C18 C17 112.43(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 O1 C1 C2 C6 -3.6(3) . . . . ? N1 C1 C2 C6 176.8(2) . . . . ? O1 C1 C2 C3 176.5(2) . . . . ? N1 C1 C2 C3 -3.2(3) . . . . ? C6 C2 C3 C4 -1.0(3) . . . . ? C1 C2 C3 C4 178.93(19) . . . . ? C2 C3 C4 C5 0.1(3) . . . . ? C6 N2 C5 C4 -0.9(3) . . . . ? C3 C4 C5 N2 0.9(4) . . . . ? C5 N2 C6 C2 0.0(3) . . . . ? C3 C2 C6 N2 1.0(3) . . . . ? C1 C2 C6 N2 -178.96(18) . . . . ? C10 N4 C7 O4 179.70(19) . . . . ? C10 N4 C7 C8 0.0(3) . . . . ? O4 C7 C8 C9 -179.3(2) . . . . ? N4 C7 C8 C9 0.4(3) . . . . ? O4 C7 C8 F1 -0.4(3) . . . . ? N4 C7 C8 F1 179.26(18) . . . . ? F1 C8 C9 N3 -179.71(19) . . . . ? C7 C8 C9 N3 -0.9(3) . . . . ? C10 N3 C9 C8 1.0(3) . . . . ? C9 N3 C10 O3 179.8(2) . . . . ? C9 N3 C10 N4 -0.6(3) . . . . ? C7 N4 C10 O3 179.7(2) . . . . ? C7 N4 C10 N3 0.0(3) . . . . ? C14 N5 C11 C12 0.0(3) . . . . ? N5 C11 C12 F2 -179.86(17) . . . . ? N5 C11 C12 C13 0.8(3) . . . . ? C14 N6 C13 O7 179.2(2) . . . . ? C14 N6 C13 C12 -0.3(3) . . . . ? C11 C12 C13 O7 179.9(2) . . . . ? F2 C12 C13 O7 0.5(3) . . . . ? C11 C12 C13 N6 -0.6(3) . . . . ? F2 C12 C13 N6 179.98(16) . . . . ? C11 N5 C14 O2 178.86(19) . . . . ? C11 N5 C14 N6 -0.8(3) . . . . ? C13 N6 C14 O2 -178.69(19) . . . . ? C13 N6 C14 N5 0.9(3) . . . . ? C16 N8 C15 O6 180.0(2) . . . . ? C16 N8 C15 N7 -0.4(3) . . . . ? C18 N7 C15 O6 179.47(19) . . . . ? C18 N7 C15 N8 -0.2(3) . . . . ? C15 N8 C16 C17 0.2(3) . . . . ? N8 C16 C17 F3 178.87(19) . . . . ? N8 C16 C17 C18 0.4(4) . . . . ? C15 N7 C18 O5 -179.2(2) . . . . ? C15 N7 C18 C17 0.8(3) . . . . ? C16 C17 C18 O5 179.2(2) . . . . ? F3 C17 C18 O5 0.7(3) . . . . ? C16 C17 C18 N7 -0.9(3) . . . . ? F3 C17 C18 N7 -179.40(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 N5 H5N N2 0.871(10) 1.967(10) 2.837(2) 176(2) . N1 H1N1 O1 0.862(9) 2.027(9) 2.887(2) 175.6(19) 2_755 N4 H4N O5 0.867(10) 2.018(10) 2.883(2) 175(2) . N1 H1N2 O7 0.849(9) 2.030(10) 2.875(2) 174(2) 1_554 N3 H3N O3 0.856(9) 1.950(10) 2.803(2) 174(2) 2_656 N6 H6N O1W 0.863(10) 1.952(10) 2.813(2) 175(2) 2_756 N8 H8N O6 0.92(2) 1.90(2) 2.810(2) 172(2) 2_657 O1W H1W1 O1 0.861(9) 1.950(9) 2.810(2) 176.9(19) . O1W H1W2 O2 0.859(9) 2.005(11) 2.856(2) 170.2(19) . N7 H7N O3 0.882(9) 1.915(10) 2.793(2) 174(2) . _diffrn_measured_fraction_theta_max 0.987 _diffrn_reflns_theta_full 27.56 _diffrn_measured_fraction_theta_full 0.987 _refine_diff_density_max 0.215 _refine_diff_density_min -0.205 _refine_diff_density_rms 0.047