data_2 _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C21 H16 F N2 O8 V' _chemical_formula_weight 494.30 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' 'V' 'V' 0.0687 2.1097 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Orthorhombic _symmetry_space_group_name_H-M Pbca loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, -y, z+1/2' '-x, y+1/2, -z+1/2' 'x+1/2, -y+1/2, -z' '-x, -y, -z' 'x-1/2, y, -z-1/2' 'x, -y-1/2, z-1/2' '-x-1/2, y-1/2, z' _cell_length_a 8.6357(3) _cell_length_b 14.3372(5) _cell_length_c 32.6037(12) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 4036.7(2) _cell_formula_units_Z 8 _cell_measurement_temperature 298(2) _cell_measurement_reflns_used 16461 _cell_measurement_theta_min 2.70 _cell_measurement_theta_max 72.30 _exptl_crystal_description block _exptl_crystal_colour brown _exptl_crystal_size_max 0.33 _exptl_crystal_size_mid 0.30 _exptl_crystal_size_min 0.28 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.627 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 2016 _exptl_absorpt_coefficient_mu 4.692 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.3066 _exptl_absorpt_correction_T_max 0.3533 _exptl_absorpt_process_details SADABS _exptl_special_details ; ? ; _diffrn_ambient_temperature 298(2) _diffrn_radiation_wavelength 1.54178 _diffrn_radiation_type CuK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type ? _diffrn_measurement_method ? _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 36089 _diffrn_reflns_av_R_equivalents 0.0551 _diffrn_reflns_av_sigmaI/netI 0.0309 _diffrn_reflns_limit_h_min -10 _diffrn_reflns_limit_h_max 10 _diffrn_reflns_limit_k_min -17 _diffrn_reflns_limit_k_max 17 _diffrn_reflns_limit_l_min -40 _diffrn_reflns_limit_l_max 33 _diffrn_reflns_theta_min 5.43 _diffrn_reflns_theta_max 72.83 _reflns_number_total 4008 _reflns_number_gt 3262 _reflns_threshold_expression >2sigma(I) _computing_data_collection ? _computing_cell_refinement ? _computing_data_reduction ? _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics ? _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^)+(0.0609P)^2^+2.8059P] 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 4008 _refine_ls_number_parameters 300 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0615 _refine_ls_R_factor_gt 0.0485 _refine_ls_wR_factor_ref 0.1271 _refine_ls_wR_factor_gt 0.1199 _refine_ls_goodness_of_fit_ref 1.080 _refine_ls_restrained_S_all 1.080 _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 V1 V 0.09622(5) 0.96286(3) 0.391338(14) 0.03835(16) Uani 1 1 d . . . F1 F -0.6657(2) 0.68990(16) 0.29919(7) 0.0797(6) Uani 1 1 d . . . N1 N 0.1132(2) 0.93019(16) 0.32923(7) 0.0407(5) Uani 1 1 d . . . N2 N -0.0145(3) 0.88614(17) 0.31172(7) 0.0462(6) Uani 1 1 d . . . O1 O 0.3075(2) 0.97979(15) 0.38748(6) 0.0475(5) Uani 1 1 d . . . O2 O -0.0958(2) 0.89921(14) 0.37810(6) 0.0443(5) Uani 1 1 d . . . O3 O 0.5614(2) 1.06443(16) 0.40962(6) 0.0539(5) Uani 1 1 d . . . O4 O 0.1700(2) 0.81277(13) 0.40397(6) 0.0468(5) Uani 1 1 d . . . O5 O 0.0622(2) 0.95128(12) 0.44774(6) 0.0430(4) Uani 1 1 d . . . O6 O 0.0620(3) 0.76585(15) 0.52248(6) 0.0552(5) Uani 1 1 d . . . O7 O 0.0413(3) 1.06744(15) 0.38674(7) 0.0594(6) Uani 1 1 d . . . O8 O -0.0316(4) 0.5866(2) 0.53546(10) 0.0997(10) Uani 1 1 d . . . H8 H -0.0322 0.5433 0.5519 0.150 Uiso 1 1 calc R . . C1 C 0.3661(3) 0.99556(19) 0.31627(9) 0.0390(6) Uani 1 1 d . . . C2 C 0.4006(3) 1.01091(18) 0.35746(9) 0.0383(6) Uani 1 1 d . . . C3 C 0.5395(3) 1.05479(18) 0.36847(9) 0.0416(6) Uani 1 1 d . . . C4 C 0.6418(3) 1.0821(2) 0.33834(10) 0.0491(7) Uani 1 1 d . . . H4 H 0.7337 1.1116 0.3455 0.059 Uiso 1 1 calc R . . C5 C 0.6085(3) 1.0659(2) 0.29741(10) 0.0527(8) Uani 1 1 d . . . H5 H 0.6786 1.0844 0.2774 0.063 Uiso 1 1 calc R . . C6 C 0.4734(4) 1.0227(2) 0.28609(9) 0.0493(7) Uani 1 1 d . . . H6 H 0.4528 1.0114 0.2585 0.059 Uiso 1 1 calc R . . C7 C 0.2254(3) 0.94975(19) 0.30432(8) 0.0419(6) Uani 1 1 d . . . H7 H 0.2140 0.9330 0.2769 0.050 Uiso 1 1 calc R . . C8 C -0.1176(3) 0.87287(18) 0.33992(8) 0.0397(6) Uani 1 1 d . . . C9 C -0.2642(3) 0.82576(17) 0.32912(8) 0.0384(6) Uani 1 1 d . . . C10 C -0.2863(3) 0.7912(2) 0.28998(9) 0.0449(6) Uani 1 1 d . . . H10 H -0.2090 0.7989 0.2704 0.054 Uiso 1 1 calc R . . C11 C -0.4212(3) 0.7456(2) 0.27958(10) 0.0519(7) Uani 1 1 d . . . H11 H -0.4362 0.7227 0.2532 0.062 Uiso 1 1 calc R . . C12 C -0.5327(3) 0.7348(2) 0.30908(10) 0.0517(7) Uani 1 1 d . . . C13 C -0.5168(3) 0.7686(2) 0.34828(10) 0.0492(7) Uani 1 1 d . . . H13 H -0.5949 0.7607 0.3676 0.059 Uiso 1 1 calc R . . C14 C -0.3814(3) 0.81485(19) 0.35810(9) 0.0434(6) Uani 1 1 d . . . H14 H -0.3684 0.8390 0.3844 0.052 Uiso 1 1 calc R . . C15 C 0.6846(4) 1.1215(3) 0.42318(12) 0.0742(11) Uani 1 1 d . . . H15A H 0.7814 1.0942 0.4151 0.111 Uiso 1 1 calc R . . H15B H 0.6812 1.1266 0.4525 0.111 Uiso 1 1 calc R . . H15C H 0.6750 1.1823 0.4112 0.111 Uiso 1 1 calc R . . C16 C 0.1411(3) 0.79421(19) 0.44064(9) 0.0411(6) Uani 1 1 d . . . C17 C 0.0791(3) 0.86747(19) 0.46604(9) 0.0415(6) Uani 1 1 d . . . C18 C 0.0424(4) 0.8512(2) 0.50530(9) 0.0493(7) Uani 1 1 d . . . H18 H 0.0026 0.8995 0.5211 0.059 Uiso 1 1 calc R . . C19 C 0.1191(4) 0.6944(2) 0.49961(9) 0.0497(7) Uani 1 1 d . . . C20 C 0.1603(4) 0.7054(2) 0.46008(9) 0.0482(7) Uani 1 1 d . . . H20 H 0.2010 0.6554 0.4454 0.058 Uiso 1 1 calc R . . C21 C 0.1251(5) 0.6062(2) 0.52328(11) 0.0666(9) Uani 1 1 d . . . H21A H 0.1656 0.5560 0.5064 0.080 Uiso 1 1 calc R . . H21B H 0.1910 0.6132 0.5472 0.080 Uiso 1 1 calc R . . 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 V1 0.0377(3) 0.0395(3) 0.0378(3) 0.0007(2) 0.00210(19) -0.0029(2) F1 0.0578(11) 0.0926(15) 0.0888(15) -0.0006(12) -0.0115(11) -0.0332(11) N1 0.0365(12) 0.0468(12) 0.0387(12) 0.0028(10) -0.0002(10) -0.0036(10) N2 0.0402(12) 0.0567(14) 0.0418(12) -0.0016(11) -0.0010(10) -0.0107(11) O1 0.0396(10) 0.0641(13) 0.0389(10) 0.0064(9) -0.0001(8) -0.0139(9) O2 0.0384(10) 0.0532(11) 0.0414(10) -0.0010(9) 0.0016(8) -0.0062(9) O3 0.0476(11) 0.0622(13) 0.0518(12) -0.0003(10) -0.0043(10) -0.0166(10) O4 0.0550(12) 0.0481(11) 0.0373(10) -0.0007(9) 0.0094(9) 0.0042(9) O5 0.0482(10) 0.0401(10) 0.0408(10) -0.0050(8) 0.0031(8) -0.0020(8) O6 0.0713(14) 0.0539(12) 0.0404(11) 0.0007(9) 0.0062(10) -0.0027(11) O7 0.0647(14) 0.0435(11) 0.0699(15) 0.0053(10) 0.0029(11) 0.0005(11) O8 0.112(2) 0.093(2) 0.094(2) 0.0332(17) 0.0145(18) -0.0154(19) C1 0.0362(13) 0.0376(13) 0.0432(14) 0.0050(12) 0.0052(11) -0.0011(11) C2 0.0357(13) 0.0335(12) 0.0456(15) 0.0051(11) 0.0036(11) 0.0006(11) C3 0.0405(14) 0.0340(13) 0.0503(16) 0.0006(12) -0.0006(13) 0.0000(11) C4 0.0404(14) 0.0432(15) 0.0637(19) 0.0018(14) 0.0050(14) -0.0105(13) C5 0.0474(16) 0.0555(18) 0.0551(18) 0.0063(15) 0.0127(14) -0.0114(14) C6 0.0489(16) 0.0547(17) 0.0442(15) 0.0042(13) 0.0085(13) -0.0020(14) C7 0.0407(15) 0.0476(15) 0.0375(13) 0.0009(12) 0.0022(12) -0.0009(12) C8 0.0398(14) 0.0381(13) 0.0412(14) 0.0025(12) -0.0008(12) 0.0016(11) C9 0.0368(13) 0.0331(13) 0.0453(14) 0.0045(11) -0.0009(11) 0.0017(11) C10 0.0425(15) 0.0499(16) 0.0423(14) 0.0017(13) 0.0016(12) -0.0016(13) C11 0.0521(17) 0.0547(17) 0.0489(17) -0.0030(14) -0.0097(14) -0.0061(14) C12 0.0432(15) 0.0433(16) 0.069(2) 0.0064(15) -0.0083(15) -0.0091(13) C13 0.0403(15) 0.0452(15) 0.0620(18) 0.0068(14) 0.0078(14) -0.0017(13) C14 0.0445(15) 0.0389(13) 0.0468(15) 0.0004(12) 0.0022(12) 0.0019(12) C15 0.0481(18) 0.105(3) 0.070(2) -0.025(2) 0.0015(16) -0.0255(19) C16 0.0366(13) 0.0444(14) 0.0422(15) -0.0010(12) 0.0008(12) -0.0039(12) C17 0.0400(14) 0.0418(14) 0.0426(15) -0.0026(12) -0.0007(12) -0.0030(11) C18 0.0578(17) 0.0461(15) 0.0440(16) -0.0073(13) 0.0038(14) -0.0004(14) C19 0.0554(17) 0.0464(16) 0.0472(16) 0.0009(14) -0.0021(14) -0.0024(13) C20 0.0521(16) 0.0451(15) 0.0473(16) -0.0017(13) 0.0026(14) -0.0001(13) C21 0.087(3) 0.059(2) 0.0535(19) 0.0114(16) 0.0038(18) -0.0027(19) _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 V1 O7 1.580(2) . ? V1 O1 1.845(2) . ? V1 O5 1.8696(19) . ? V1 O2 1.9412(19) . ? V1 N1 2.084(2) . ? V1 O4 2.282(2) . ? F1 C12 1.356(3) . ? N1 C7 1.295(3) . ? N1 N2 1.394(3) . ? N2 C8 1.294(3) . ? O1 C2 1.343(3) . ? O2 C8 1.314(3) . ? O3 C3 1.362(4) . ? O3 C15 1.413(4) . ? O4 C16 1.250(3) . ? O5 C17 1.350(3) . ? O6 C18 1.356(4) . ? O6 C19 1.359(4) . ? O8 C21 1.439(5) . ? O8 H8 0.8200 . ? C1 C2 1.393(4) . ? C1 C6 1.407(4) . ? C1 C7 1.435(4) . ? C2 C3 1.401(4) . ? C3 C4 1.378(4) . ? C4 C5 1.384(4) . ? C4 H4 0.9300 . ? C5 C6 1.371(4) . ? C5 H5 0.9300 . ? C6 H6 0.9300 . ? C7 H7 0.9300 . ? C8 C9 1.477(4) . ? C9 C10 1.382(4) . ? C9 C14 1.394(4) . ? C10 C11 1.379(4) . ? C10 H10 0.9300 . ? C11 C12 1.369(4) . ? C11 H11 0.9300 . ? C12 C13 1.374(5) . ? C13 C14 1.381(4) . ? C13 H13 0.9300 . ? C14 H14 0.9300 . ? C15 H15A 0.9600 . ? C15 H15B 0.9600 . ? C15 H15C 0.9600 . ? C16 C20 1.432(4) . ? C16 C17 1.441(4) . ? C17 C18 1.339(4) . ? C18 H18 0.9300 . ? C19 C20 1.346(4) . ? C19 C21 1.483(4) . ? C20 H20 0.9300 . ? C21 H21A 0.9700 . ? C21 H21B 0.9700 . ? 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 O7 V1 O1 99.52(11) . . ? O7 V1 O5 97.49(10) . . ? O1 V1 O5 103.54(8) . . ? O7 V1 O2 99.72(11) . . ? O1 V1 O2 153.05(9) . . ? O5 V1 O2 92.45(8) . . ? O7 V1 N1 98.18(11) . . ? O1 V1 N1 83.89(8) . . ? O5 V1 N1 161.27(9) . . ? O2 V1 N1 74.84(8) . . ? O7 V1 O4 174.94(10) . . ? O1 V1 O4 81.97(9) . . ? O5 V1 O4 77.44(7) . . ? O2 V1 O4 80.51(8) . . ? N1 V1 O4 86.77(8) . . ? C7 N1 N2 115.7(2) . . ? C7 N1 V1 127.86(19) . . ? N2 N1 V1 116.36(16) . . ? C8 N2 N1 108.7(2) . . ? C2 O1 V1 133.26(17) . . ? C8 O2 V1 117.91(16) . . ? C3 O3 C15 118.2(2) . . ? C16 O4 V1 108.53(17) . . ? C17 O5 V1 119.80(16) . . ? C18 O6 C19 119.9(2) . . ? C21 O8 H8 109.5 . . ? C2 C1 C6 119.3(3) . . ? C2 C1 C7 121.0(2) . . ? C6 C1 C7 119.6(3) . . ? O1 C2 C1 121.5(2) . . ? O1 C2 C3 118.3(2) . . ? C1 C2 C3 120.1(2) . . ? O3 C3 C4 125.8(3) . . ? O3 C3 C2 114.7(2) . . ? C4 C3 C2 119.6(3) . . ? C3 C4 C5 120.4(3) . . ? C3 C4 H4 119.8 . . ? C5 C4 H4 119.8 . . ? C6 C5 C4 120.8(3) . . ? C6 C5 H5 119.6 . . ? C4 C5 H5 119.6 . . ? C5 C6 C1 119.8(3) . . ? C5 C6 H6 120.1 . . ? C1 C6 H6 120.1 . . ? N1 C7 C1 124.2(3) . . ? N1 C7 H7 117.9 . . ? C1 C7 H7 117.9 . . ? N2 C8 O2 122.2(2) . . ? N2 C8 C9 119.2(2) . . ? O2 C8 C9 118.7(2) . . ? C10 C9 C14 119.0(2) . . ? C10 C9 C8 120.1(2) . . ? C14 C9 C8 120.8(2) . . ? C11 C10 C9 120.9(3) . . ? C11 C10 H10 119.5 . . ? C9 C10 H10 119.5 . . ? C12 C11 C10 118.4(3) . . ? C12 C11 H11 120.8 . . ? C10 C11 H11 120.8 . . ? F1 C12 C11 118.8(3) . . ? F1 C12 C13 118.2(3) . . ? C11 C12 C13 122.9(3) . . ? C12 C13 C14 118.0(3) . . ? C12 C13 H13 121.0 . . ? C14 C13 H13 121.0 . . ? C13 C14 C9 120.8(3) . . ? C13 C14 H14 119.6 . . ? C9 C14 H14 119.6 . . ? O3 C15 H15A 109.5 . . ? O3 C15 H15B 109.5 . . ? H15A C15 H15B 109.5 . . ? O3 C15 H15C 109.5 . . ? H15A C15 H15C 109.5 . . ? H15B C15 H15C 109.5 . . ? O4 C16 C20 126.1(3) . . ? O4 C16 C17 117.9(2) . . ? C20 C16 C17 115.9(3) . . ? C18 C17 O5 123.5(3) . . ? C18 C17 C16 120.7(3) . . ? O5 C17 C16 115.8(2) . . ? C17 C18 O6 121.5(3) . . ? C17 C18 H18 119.3 . . ? O6 C18 H18 119.3 . . ? C20 C19 O6 122.2(3) . . ? C20 C19 C21 126.1(3) . . ? O6 C19 C21 111.7(3) . . ? C19 C20 C16 119.8(3) . . ? C19 C20 H20 120.1 . . ? C16 C20 H20 120.1 . . ? O8 C21 C19 106.1(3) . . ? O8 C21 H21A 110.5 . . ? C19 C21 H21A 110.5 . . ? O8 C21 H21B 110.5 . . ? C19 C21 H21B 110.5 . . ? H21A C21 H21B 108.7 . . ? 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 O8 H8 O1 0.82 2.44 3.025(4) 129.5 4_466 O8 H8 O3 0.82 2.15 2.923(4) 157.5 4_466 _diffrn_measured_fraction_theta_max 0.995 _diffrn_reflns_theta_full 72.83 _diffrn_measured_fraction_theta_full 0.995 _refine_diff_density_max 0.809 _refine_diff_density_min -0.421 _refine_diff_density_rms 0.102