data_1 _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C21 H14 Br F N3 O5 V' _chemical_formula_weight 538.20 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' 'V' 'V' 0.3005 0.5294 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 'Br' 'Br' -0.2901 2.4595 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M P21/c 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 10.0532(8) _cell_length_b 17.2727(15) _cell_length_c 12.1902(10) _cell_angle_alpha 90.00 _cell_angle_beta 102.511(2) _cell_angle_gamma 90.00 _cell_volume 2066.5(3) _cell_formula_units_Z 4 _cell_measurement_temperature 298(2) _cell_measurement_reflns_used 8435 _cell_measurement_theta_min 2.36 _cell_measurement_theta_max 25.78 _exptl_crystal_description block _exptl_crystal_colour brown _exptl_crystal_size_max 0.23 _exptl_crystal_size_mid 0.23 _exptl_crystal_size_min 0.22 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.730 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1072 _exptl_absorpt_coefficient_mu 2.463 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.6012 _exptl_absorpt_correction_T_max 0.6133 _exptl_absorpt_process_details SADABS _exptl_special_details ; ? ; _diffrn_ambient_temperature 298(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 ? _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 19286 _diffrn_reflns_av_R_equivalents 0.0449 _diffrn_reflns_av_sigmaI/netI 0.0398 _diffrn_reflns_limit_h_min -11 _diffrn_reflns_limit_h_max 12 _diffrn_reflns_limit_k_min -20 _diffrn_reflns_limit_k_max 20 _diffrn_reflns_limit_l_min -14 _diffrn_reflns_limit_l_max 14 _diffrn_reflns_theta_min 2.08 _diffrn_reflns_theta_max 25.50 _reflns_number_total 3835 _reflns_number_gt 2928 _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^)+(0.0709P)^2^+2.8650P] 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 3835 _refine_ls_number_parameters 293 _refine_ls_number_restraints 1 _refine_ls_R_factor_all 0.0692 _refine_ls_R_factor_gt 0.0462 _refine_ls_wR_factor_ref 0.1366 _refine_ls_wR_factor_gt 0.1213 _refine_ls_goodness_of_fit_ref 1.057 _refine_ls_restrained_S_all 1.057 _refine_ls_shift/su_max 0.001 _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 0.90212(7) 0.86697(4) 0.35173(5) 0.0314(2) Uani 1 1 d . . . Br1 Br 0.41319(5) 1.17255(3) 0.42611(5) 0.0565(2) Uani 1 1 d . . . F1 F 1.1917(4) 0.8843(3) 0.7889(3) 0.1064(14) Uani 1 1 d . . . N1 N 0.8932(3) 0.91370(17) 0.5072(3) 0.0289(7) Uani 1 1 d . . . N2 N 0.9864(3) 0.88444(18) 0.5996(3) 0.0313(7) Uani 1 1 d . . . N3 N 0.9091(4) 0.71638(19) 0.2768(3) 0.0347(8) Uani 1 1 d D . . O1 O 0.7190(3) 0.89608(17) 0.3129(2) 0.0410(7) Uani 1 1 d . . . O2 O 1.0665(3) 0.83119(16) 0.4553(2) 0.0379(7) Uani 1 1 d . . . O3 O 0.8236(3) 0.76205(16) 0.4154(2) 0.0391(7) Uani 1 1 d . . . O4 O 0.9239(3) 0.79151(16) 0.2483(2) 0.0358(6) Uani 1 1 d . . . O5 O 0.9656(3) 0.93668(18) 0.2964(2) 0.0469(8) Uani 1 1 d . . . C1 C 0.7004(4) 0.9976(2) 0.4418(3) 0.0327(9) Uani 1 1 d . . . C2 C 0.6584(4) 0.9595(2) 0.3386(3) 0.0355(9) Uani 1 1 d . . . C3 C 0.5437(4) 0.9876(3) 0.2625(4) 0.0451(11) Uani 1 1 d . . . H3A H 0.5142 0.9631 0.1936 0.054 Uiso 1 1 calc R . . C4 C 0.4748(4) 1.0509(3) 0.2889(4) 0.0464(11) Uani 1 1 d . . . H4 H 0.3995 1.0695 0.2374 0.056 Uiso 1 1 calc R . . C5 C 0.5169(4) 1.0876(2) 0.3921(4) 0.0388(10) Uani 1 1 d . . . C6 C 0.6278(4) 1.0612(2) 0.4680(4) 0.0360(9) Uani 1 1 d . . . H6 H 0.6550 1.0856 0.5373 0.043 Uiso 1 1 calc R . . C7 C 0.8111(4) 0.9666(2) 0.5265(3) 0.0325(9) Uani 1 1 d . . . H7 H 0.8236 0.9860 0.5992 0.039 Uiso 1 1 calc R . . C8 C 1.0734(4) 0.8423(2) 0.5621(3) 0.0310(9) Uani 1 1 d . . . C9 C 1.1858(4) 0.8030(2) 0.6407(3) 0.0365(9) Uani 1 1 d . . . C10 C 1.2420(5) 0.8265(3) 0.7462(4) 0.0571(14) Uani 1 1 d . . . C11 C 1.3506(6) 0.7894(5) 0.8153(5) 0.080(2) Uani 1 1 d . . . H11 H 1.3874 0.8075 0.8873 0.096 Uiso 1 1 calc R . . C12 C 1.4025(7) 0.7240(4) 0.7729(6) 0.085(2) Uani 1 1 d . . . H12 H 1.4747 0.6973 0.8175 0.102 Uiso 1 1 calc R . . C13 C 1.3497(8) 0.6989(4) 0.6683(7) 0.094(2) Uani 1 1 d . . . H13 H 1.3876 0.6558 0.6411 0.113 Uiso 1 1 calc R . . C14 C 1.2418(6) 0.7352(3) 0.6012(6) 0.0754(18) Uani 1 1 d . . . H14 H 1.2047 0.7158 0.5300 0.090 Uiso 1 1 calc R . . C15 C 0.8360(4) 0.6242(2) 0.4030(3) 0.0334(9) Uani 1 1 d . . . C16 C 0.7721(5) 0.6148(3) 0.4915(4) 0.0493(12) Uani 1 1 d . . . H16 H 0.7432 0.6579 0.5258 0.059 Uiso 1 1 calc R . . C17 C 0.7510(6) 0.5415(3) 0.5289(4) 0.0587(14) Uani 1 1 d . . . H17 H 0.7080 0.5353 0.5886 0.070 Uiso 1 1 calc R . . C18 C 0.7930(5) 0.4778(3) 0.4790(4) 0.0496(12) Uani 1 1 d . . . H18 H 0.7771 0.4286 0.5042 0.060 Uiso 1 1 calc R . . C19 C 0.8590(5) 0.4860(3) 0.3912(4) 0.0434(10) Uani 1 1 d . . . H19 H 0.8879 0.4426 0.3578 0.052 Uiso 1 1 calc R . . C20 C 0.8818(4) 0.5593(2) 0.3536(3) 0.0361(9) Uani 1 1 d . . . H20 H 0.9276 0.5654 0.2956 0.043 Uiso 1 1 calc R . . C21 C 0.8554(4) 0.7039(2) 0.3658(3) 0.0323(9) Uani 1 1 d . . . H3 H 0.928(5) 0.682(2) 0.227(3) 0.048(13) 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 V1 0.0378(4) 0.0301(4) 0.0270(3) -0.0027(3) 0.0086(3) -0.0046(3) Br1 0.0445(3) 0.0463(3) 0.0771(4) 0.0029(2) 0.0099(3) 0.0109(2) F1 0.099(3) 0.129(3) 0.076(2) -0.034(2) -0.012(2) 0.037(3) N1 0.0296(17) 0.0282(16) 0.0289(16) -0.0007(13) 0.0062(14) -0.0060(14) N2 0.0346(18) 0.0299(17) 0.0281(17) 0.0011(13) 0.0043(15) 0.0007(14) N3 0.045(2) 0.0314(18) 0.0300(18) -0.0046(14) 0.0133(16) -0.0023(15) O1 0.0418(17) 0.0408(16) 0.0369(16) -0.0089(13) 0.0005(14) -0.0014(13) O2 0.0360(16) 0.0489(17) 0.0306(15) -0.0022(12) 0.0110(13) 0.0049(13) O3 0.0524(18) 0.0326(15) 0.0386(16) -0.0077(13) 0.0235(14) -0.0079(13) O4 0.0461(17) 0.0337(15) 0.0296(14) -0.0033(11) 0.0125(13) -0.0041(12) O5 0.061(2) 0.0443(18) 0.0374(16) -0.0006(13) 0.0151(15) -0.0138(15) C1 0.029(2) 0.033(2) 0.036(2) 0.0022(17) 0.0068(17) -0.0054(17) C2 0.035(2) 0.033(2) 0.038(2) 0.0021(18) 0.0075(19) -0.0065(17) C3 0.036(2) 0.054(3) 0.040(2) -0.002(2) -0.001(2) -0.006(2) C4 0.032(2) 0.049(3) 0.052(3) 0.009(2) -0.001(2) 0.001(2) C5 0.030(2) 0.037(2) 0.050(3) 0.0048(19) 0.011(2) -0.0020(18) C6 0.035(2) 0.035(2) 0.038(2) 0.0009(18) 0.0077(19) -0.0045(18) C7 0.036(2) 0.031(2) 0.030(2) -0.0021(16) 0.0087(18) -0.0037(17) C8 0.033(2) 0.0260(19) 0.035(2) 0.0013(16) 0.0098(18) -0.0068(16) C9 0.035(2) 0.038(2) 0.036(2) 0.0097(18) 0.0066(19) -0.0037(18) C10 0.045(3) 0.085(4) 0.043(3) -0.007(3) 0.014(2) 0.009(3) C11 0.064(4) 0.134(6) 0.036(3) 0.015(3) 0.000(3) -0.001(4) C12 0.069(4) 0.090(5) 0.093(5) 0.037(4) 0.009(4) 0.027(4) C13 0.096(5) 0.059(4) 0.112(6) 0.001(4) -0.012(5) 0.028(4) C14 0.061(4) 0.058(3) 0.104(5) 0.026(3) 0.010(3) 0.028(3) C15 0.033(2) 0.036(2) 0.031(2) -0.0035(17) 0.0046(17) -0.0078(17) C16 0.068(3) 0.045(3) 0.042(3) -0.007(2) 0.027(2) -0.006(2) C17 0.083(4) 0.057(3) 0.044(3) 0.000(2) 0.032(3) -0.020(3) C18 0.066(3) 0.036(2) 0.046(3) 0.004(2) 0.013(2) -0.009(2) C19 0.051(3) 0.033(2) 0.045(3) -0.0010(19) 0.008(2) 0.002(2) C20 0.035(2) 0.039(2) 0.036(2) -0.0025(18) 0.0097(18) -0.0018(18) C21 0.030(2) 0.033(2) 0.034(2) -0.0069(17) 0.0085(18) -0.0066(17) _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 O5 1.581(3) . ? V1 O4 1.859(3) . ? V1 O1 1.867(3) . ? V1 O2 1.950(3) . ? V1 N1 2.079(3) . ? V1 O3 2.185(3) . ? Br1 C5 1.898(4) . ? F1 C10 1.279(6) . ? N1 C7 1.287(5) . ? N1 N2 1.394(5) . ? N2 C8 1.296(5) . ? N3 C21 1.330(5) . ? N3 O4 1.360(4) . ? N3 H3 0.899(10) . ? O1 C2 1.324(5) . ? O2 C8 1.302(5) . ? O3 C21 1.249(5) . ? C1 C6 1.393(6) . ? C1 C2 1.402(6) . ? C1 C7 1.447(6) . ? C2 C3 1.401(6) . ? C3 C4 1.370(7) . ? C3 H3A 0.9300 . ? C4 C5 1.390(6) . ? C4 H4 0.9300 . ? C5 C6 1.364(6) . ? C6 H6 0.9300 . ? C7 H7 0.9300 . ? C8 C9 1.478(6) . ? C9 C10 1.350(7) . ? C9 C14 1.428(7) . ? C10 C11 1.383(8) . ? C11 C12 1.391(10) . ? C11 H11 0.9300 . ? C12 C13 1.342(10) . ? C12 H12 0.9300 . ? C13 C14 1.361(8) . ? C13 H13 0.9300 . ? C14 H14 0.9300 . ? C15 C16 1.380(6) . ? C15 C20 1.397(6) . ? C15 C21 1.475(6) . ? C16 C17 1.377(7) . ? C16 H16 0.9300 . ? C17 C18 1.369(7) . ? C17 H17 0.9300 . ? C18 C19 1.383(7) . ? C18 H18 0.9300 . ? C19 C20 1.381(6) . ? C19 H19 0.9300 . ? C20 H20 0.9300 . ? 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 O5 V1 O4 97.28(14) . . ? O5 V1 O1 98.83(16) . . ? O4 V1 O1 105.73(13) . . ? O5 V1 O2 98.85(15) . . ? O4 V1 O2 90.54(12) . . ? O1 V1 O2 154.15(13) . . ? O5 V1 N1 101.21(14) . . ? O4 V1 N1 157.66(13) . . ? O1 V1 N1 83.80(13) . . ? O2 V1 N1 74.37(12) . . ? O5 V1 O3 173.51(14) . . ? O4 V1 O3 76.37(11) . . ? O1 V1 O3 84.34(12) . . ? O2 V1 O3 80.08(12) . . ? N1 V1 O3 84.72(11) . . ? C7 N1 N2 117.0(3) . . ? C7 N1 V1 126.8(3) . . ? N2 N1 V1 116.2(2) . . ? C8 N2 N1 107.8(3) . . ? C21 N3 O4 116.7(3) . . ? C21 N3 H3 129(3) . . ? O4 N3 H3 114(3) . . ? C2 O1 V1 130.0(3) . . ? C8 O2 V1 117.0(2) . . ? C21 O3 V1 110.2(2) . . ? N3 O4 V1 117.4(2) . . ? C6 C1 C2 120.3(4) . . ? C6 C1 C7 119.2(4) . . ? C2 C1 C7 120.2(4) . . ? O1 C2 C3 119.0(4) . . ? O1 C2 C1 122.4(4) . . ? C3 C2 C1 118.5(4) . . ? C4 C3 C2 120.5(4) . . ? C4 C3 H3A 119.8 . . ? C2 C3 H3A 119.8 . . ? C3 C4 C5 120.4(4) . . ? C3 C4 H4 119.8 . . ? C5 C4 H4 119.8 . . ? C6 C5 C4 120.4(4) . . ? C6 C5 Br1 121.2(3) . . ? C4 C5 Br1 118.4(3) . . ? C5 C6 C1 120.0(4) . . ? C5 C6 H6 120.0 . . ? C1 C6 H6 120.0 . . ? N1 C7 C1 123.8(4) . . ? N1 C7 H7 118.1 . . ? C1 C7 H7 118.1 . . ? N2 C8 O2 122.8(4) . . ? N2 C8 C9 120.6(4) . . ? O2 C8 C9 116.6(4) . . ? C10 C9 C14 117.0(5) . . ? C10 C9 C8 125.7(4) . . ? C14 C9 C8 117.4(4) . . ? F1 C10 C9 120.1(5) . . ? F1 C10 C11 116.3(5) . . ? C9 C10 C11 123.6(5) . . ? C10 C11 C12 117.4(6) . . ? C10 C11 H11 121.3 . . ? C12 C11 H11 121.3 . . ? C13 C12 C11 120.8(6) . . ? C13 C12 H12 119.6 . . ? C11 C12 H12 119.6 . . ? C12 C13 C14 121.5(7) . . ? C12 C13 H13 119.3 . . ? C14 C13 H13 119.3 . . ? C13 C14 C9 119.7(6) . . ? C13 C14 H14 120.1 . . ? C9 C14 H14 120.1 . . ? C16 C15 C20 119.7(4) . . ? C16 C15 C21 117.8(4) . . ? C20 C15 C21 122.6(4) . . ? C17 C16 C15 119.9(4) . . ? C17 C16 H16 120.1 . . ? C15 C16 H16 120.1 . . ? C18 C17 C16 120.5(4) . . ? C18 C17 H17 119.7 . . ? C16 C17 H17 119.7 . . ? C17 C18 C19 120.5(4) . . ? C17 C18 H18 119.8 . . ? C19 C18 H18 119.8 . . ? C20 C19 C18 119.5(4) . . ? C20 C19 H19 120.2 . . ? C18 C19 H19 120.2 . . ? C19 C20 C15 119.9(4) . . ? C19 C20 H20 120.1 . . ? C15 C20 H20 120.1 . . ? O3 C21 N3 117.1(4) . . ? O3 C21 C15 122.4(4) . . ? N3 C21 C15 120.4(4) . . ? 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 N3 H3 N2 0.899(10) 2.112(13) 3.005(5) 172(4) 4_575 _diffrn_measured_fraction_theta_max 0.999 _diffrn_reflns_theta_full 25.50 _diffrn_measured_fraction_theta_full 0.999 _refine_diff_density_max 1.598 _refine_diff_density_min -0.575 _refine_diff_density_rms 0.090