data_2 _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 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 27.4352(19) _cell_length_b 7.6107(5) _cell_length_c 20.9839(14) _cell_angle_alpha 90.00 _cell_angle_beta 100.193(2) _cell_angle_gamma 90.00 _cell_volume 4312.3(5) _cell_formula_units_Z 8 _cell_measurement_temperature 298(2) _cell_measurement_reflns_used 9910 _cell_measurement_theta_min 2.26 _cell_measurement_theta_max 26.38 _exptl_crystal_description block _exptl_crystal_colour brown _exptl_crystal_size_max 0.32 _exptl_crystal_size_mid 0.30 _exptl_crystal_size_min 0.27 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.658 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 2144 _exptl_absorpt_coefficient_mu 2.360 _exptl_absorpt_correction_type ? _exptl_absorpt_correction_T_min 0.5188 _exptl_absorpt_correction_T_max 0.5682 _exptl_absorpt_process_details ? _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 20143 _diffrn_reflns_av_R_equivalents 0.0438 _diffrn_reflns_av_sigmaI/netI 0.0340 _diffrn_reflns_limit_h_min -29 _diffrn_reflns_limit_h_max 33 _diffrn_reflns_limit_k_min -9 _diffrn_reflns_limit_k_max 9 _diffrn_reflns_limit_l_min -25 _diffrn_reflns_limit_l_max 25 _diffrn_reflns_theta_min 2.26 _diffrn_reflns_theta_max 25.50 _reflns_number_total 4003 _reflns_number_gt 3256 _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^)+(0.0408P)^2^+8.6161P] 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 4003 _refine_ls_number_parameters 293 _refine_ls_number_restraints 1 _refine_ls_R_factor_all 0.0530 _refine_ls_R_factor_gt 0.0385 _refine_ls_wR_factor_ref 0.0974 _refine_ls_wR_factor_gt 0.0904 _refine_ls_goodness_of_fit_ref 1.029 _refine_ls_restrained_S_all 1.029 _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 0.161544(18) 0.38675(6) 0.11720(2) 0.03541(15) Uani 1 1 d . . . Br1 Br 0.075419(16) 0.27109(5) 0.28722(2) 0.06924(16) Uani 1 1 d . . . F1 F 0.18089(9) 0.9425(3) -0.04740(10) 0.0708(6) Uani 1 1 d . . . N1 N 0.15499(8) 0.6555(3) 0.10698(10) 0.0337(5) Uani 1 1 d . . . N2 N 0.16438(9) 0.7294(3) 0.04928(11) 0.0354(5) Uani 1 1 d . . . N3 N 0.12822(9) 0.0900(3) 0.04623(12) 0.0399(6) Uani 1 1 d D . . O1 O 0.11732(8) 0.4157(3) 0.17472(9) 0.0438(5) Uani 1 1 d . . . O2 O 0.18546(8) 0.4429(2) 0.03792(9) 0.0413(5) Uani 1 1 d . . . O3 O 0.09247(7) 0.3482(3) 0.04814(10) 0.0425(5) Uani 1 1 d . . . O4 O 0.16171(7) 0.1491(2) 0.09737(9) 0.0377(5) Uani 1 1 d . . . O5 O 0.21141(8) 0.3821(3) 0.16877(10) 0.0486(5) Uani 1 1 d . . . C1 C 0.13588(12) 0.7080(4) 0.21274(14) 0.0393(7) Uani 1 1 d . . . C2 C 0.11885(10) 0.5354(4) 0.22077(13) 0.0360(6) Uani 1 1 d . . . C3 C 0.10019(11) 0.4992(4) 0.27670(15) 0.0444(7) Uani 1 1 d . . . C4 C 0.10034(14) 0.6233(5) 0.32432(17) 0.0601(9) Uani 1 1 d . . . H4 H 0.0886 0.5944 0.3619 0.072 Uiso 1 1 calc R . . C5 C 0.11784(16) 0.7908(5) 0.31666(17) 0.0633(10) Uani 1 1 d . . . H5 H 0.1180 0.8743 0.3490 0.076 Uiso 1 1 calc R . . C6 C 0.13500(14) 0.8335(4) 0.26130(15) 0.0534(8) Uani 1 1 d . . . H6 H 0.1462 0.9469 0.2559 0.064 Uiso 1 1 calc R . . C7 C 0.14945(11) 0.7631(4) 0.15288(14) 0.0380(7) Uani 1 1 d . . . H7 H 0.1545 0.8823 0.1468 0.046 Uiso 1 1 calc R . . C8 C 0.18110(10) 0.6041(3) 0.01664(13) 0.0333(6) Uani 1 1 d . . . C9 C 0.19619(10) 0.6355(4) -0.04658(13) 0.0360(6) Uani 1 1 d . . . C10 C 0.19579(11) 0.7990(4) -0.07610(15) 0.0445(7) Uani 1 1 d . . . C11 C 0.21054(12) 0.8240(5) -0.13475(16) 0.0546(9) Uani 1 1 d . . . H11 H 0.2104 0.9357 -0.1528 0.066 Uiso 1 1 calc R . . C12 C 0.22543(13) 0.6812(6) -0.16615(16) 0.0607(10) Uani 1 1 d . . . H12 H 0.2347 0.6955 -0.2064 0.073 Uiso 1 1 calc R . . C13 C 0.22675(13) 0.5181(6) -0.13889(16) 0.0598(10) Uani 1 1 d . . . H13 H 0.2372 0.4221 -0.1604 0.072 Uiso 1 1 calc R . . C14 C 0.21266(12) 0.4950(5) -0.07962(15) 0.0500(8) Uani 1 1 d . . . H14 H 0.2142 0.3834 -0.0613 0.060 Uiso 1 1 calc R . . C15 C 0.05247(11) 0.1435(5) -0.03062(14) 0.0447(7) Uani 1 1 d . . . C16 C 0.01992(13) 0.2709(5) -0.05983(18) 0.0603(9) Uani 1 1 d . . . H16 H 0.0235 0.3867 -0.0456 0.072 Uiso 1 1 calc R . . C17 C -0.01751(16) 0.2273(8) -0.1095(2) 0.0862(14) Uani 1 1 d . . . H17 H -0.0390 0.3136 -0.1294 0.103 Uiso 1 1 calc R . . C18 C -0.02331(17) 0.0558(9) -0.1299(2) 0.0915(16) Uani 1 1 d . . . H18 H -0.0489 0.0265 -0.1634 0.110 Uiso 1 1 calc R . . C19 C 0.00806(15) -0.0718(7) -0.1015(2) 0.0780(13) Uani 1 1 d . . . H19 H 0.0037 -0.1874 -0.1157 0.094 Uiso 1 1 calc R . . C20 C 0.04647(13) -0.0298(5) -0.05162(17) 0.0579(9) Uani 1 1 d . . . H20 H 0.0680 -0.1165 -0.0323 0.069 Uiso 1 1 calc R . . C21 C 0.09158(11) 0.1991(4) 0.02307(14) 0.0378(7) Uani 1 1 d . . . H3 H 0.1345(11) -0.017(2) 0.0320(13) 0.042(8) 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 0.0480(3) 0.0230(2) 0.0360(3) 0.00185(19) 0.0095(2) 0.0003(2) Br1 0.0747(3) 0.0664(3) 0.0748(3) 0.01189(19) 0.0356(2) -0.01641(19) F1 0.1083(17) 0.0478(11) 0.0675(13) 0.0183(10) 0.0463(13) 0.0181(11) N1 0.0432(14) 0.0263(11) 0.0327(12) 0.0015(10) 0.0098(11) -0.0004(10) N2 0.0484(14) 0.0285(12) 0.0309(12) 0.0037(10) 0.0119(11) 0.0013(10) N3 0.0508(15) 0.0269(13) 0.0416(14) -0.0040(11) 0.0069(12) 0.0028(11) O1 0.0595(13) 0.0344(11) 0.0412(11) -0.0013(9) 0.0193(10) -0.0071(10) O2 0.0581(13) 0.0284(10) 0.0406(11) 0.0012(8) 0.0174(10) 0.0055(9) O3 0.0492(12) 0.0332(11) 0.0439(11) -0.0029(9) 0.0049(10) 0.0072(9) O4 0.0449(12) 0.0257(9) 0.0406(11) 0.0007(8) 0.0021(9) 0.0022(8) O5 0.0584(14) 0.0407(12) 0.0446(12) 0.0048(10) 0.0035(10) -0.0014(10) C1 0.0483(17) 0.0364(15) 0.0344(15) -0.0008(12) 0.0103(13) 0.0036(13) C2 0.0359(15) 0.0373(15) 0.0353(14) 0.0008(13) 0.0073(12) 0.0048(12) C3 0.0440(17) 0.0474(18) 0.0454(17) 0.0053(14) 0.0176(14) 0.0017(14) C4 0.071(2) 0.070(2) 0.0457(19) 0.0022(18) 0.0283(18) 0.010(2) C5 0.091(3) 0.059(2) 0.0448(19) -0.0125(17) 0.0254(19) 0.005(2) C6 0.076(2) 0.0413(17) 0.0445(18) -0.0075(15) 0.0159(17) 0.0031(17) C7 0.0505(18) 0.0278(14) 0.0359(15) 0.0002(12) 0.0084(14) -0.0003(12) C8 0.0340(15) 0.0317(14) 0.0330(14) 0.0003(12) 0.0027(12) -0.0007(12) C9 0.0341(15) 0.0418(16) 0.0316(14) 0.0003(12) 0.0043(12) 0.0024(12) C10 0.0411(17) 0.0514(18) 0.0425(17) 0.0060(15) 0.0112(14) 0.0077(15) C11 0.0495(19) 0.072(2) 0.0430(18) 0.0184(18) 0.0110(15) 0.0044(18) C12 0.0459(19) 0.103(3) 0.0339(17) 0.003(2) 0.0102(15) 0.003(2) C13 0.058(2) 0.082(3) 0.0411(18) -0.0143(19) 0.0148(16) 0.010(2) C14 0.0540(19) 0.055(2) 0.0417(17) -0.0061(15) 0.0105(15) 0.0062(16) C15 0.0414(17) 0.060(2) 0.0362(16) -0.0040(15) 0.0149(14) -0.0035(15) C16 0.050(2) 0.074(3) 0.056(2) 0.0025(19) 0.0050(17) -0.0011(18) C17 0.056(3) 0.122(4) 0.073(3) 0.004(3) -0.009(2) 0.005(3) C18 0.054(3) 0.156(5) 0.061(3) -0.028(3) -0.001(2) -0.011(3) C19 0.056(2) 0.108(4) 0.075(3) -0.051(3) 0.026(2) -0.022(2) C20 0.049(2) 0.068(2) 0.060(2) -0.0215(19) 0.0185(17) -0.0063(18) C21 0.0411(16) 0.0386(16) 0.0368(15) 0.0014(13) 0.0156(13) -0.0001(13) _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 1.587(2) . ? V1 O4 1.8564(19) . ? V1 O1 1.870(2) . ? V1 O2 1.9410(19) . ? V1 N1 2.061(2) . ? V1 O3 2.192(2) . ? Br1 C3 1.892(3) . ? F1 C10 1.345(4) . ? N1 C7 1.294(4) . ? N1 N2 1.400(3) . ? N2 C8 1.304(3) . ? N3 C21 1.328(4) . ? N3 O4 1.360(3) . ? N3 H3 0.893(10) . ? O1 C2 1.323(3) . ? O2 C8 1.304(3) . ? O3 C21 1.249(3) . ? C1 C6 1.400(4) . ? C1 C2 1.415(4) . ? C1 C7 1.434(4) . ? C2 C3 1.389(4) . ? C3 C4 1.375(5) . ? C4 C5 1.382(5) . ? C4 H4 0.9300 . ? C5 C6 1.367(5) . ? C5 H5 0.9300 . ? C6 H6 0.9300 . ? C7 H7 0.9300 . ? C8 C9 1.477(4) . ? C9 C10 1.389(4) . ? C9 C14 1.393(4) . ? C10 C11 1.375(4) . ? C11 C12 1.370(5) . ? C11 H11 0.9300 . ? C12 C13 1.365(5) . ? C12 H12 0.9300 . ? C13 C14 1.378(5) . ? C13 H13 0.9300 . ? C14 H14 0.9300 . ? C15 C16 1.385(5) . ? C15 C20 1.391(5) . ? C15 C21 1.474(4) . ? C16 C17 1.369(6) . ? C16 H16 0.9300 . ? C17 C18 1.374(7) . ? C17 H17 0.9300 . ? C18 C19 1.363(7) . ? C18 H18 0.9300 . ? C19 C20 1.385(5) . ? 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 95.47(10) . . ? O5 V1 O1 98.17(11) . . ? O4 V1 O1 106.70(9) . . ? O5 V1 O2 102.00(10) . . ? O4 V1 O2 90.45(8) . . ? O1 V1 O2 152.09(9) . . ? O5 V1 N1 98.15(10) . . ? O4 V1 N1 161.31(9) . . ? O1 V1 N1 84.00(9) . . ? O2 V1 N1 74.26(8) . . ? O5 V1 O3 170.98(9) . . ? O4 V1 O3 75.97(8) . . ? O1 V1 O3 81.88(9) . . ? O2 V1 O3 81.18(8) . . ? N1 V1 O3 90.83(8) . . ? C7 N1 N2 117.0(2) . . ? C7 N1 V1 124.78(19) . . ? N2 N1 V1 117.55(16) . . ? C8 N2 N1 107.3(2) . . ? C21 N3 O4 116.3(2) . . ? C21 N3 H3 128.7(19) . . ? O4 N3 H3 115.0(19) . . ? C2 O1 V1 127.76(18) . . ? C8 O2 V1 118.46(17) . . ? C21 O3 V1 110.48(18) . . ? N3 O4 V1 118.11(15) . . ? C6 C1 C2 119.9(3) . . ? C6 C1 C7 118.6(3) . . ? C2 C1 C7 121.2(3) . . ? O1 C2 C3 120.8(3) . . ? O1 C2 C1 121.4(2) . . ? C3 C2 C1 117.6(3) . . ? C4 C3 C2 121.6(3) . . ? C4 C3 Br1 120.1(2) . . ? C2 C3 Br1 118.3(2) . . ? C3 C4 C5 120.4(3) . . ? C3 C4 H4 119.8 . . ? C5 C4 H4 119.8 . . ? C6 C5 C4 119.8(3) . . ? C6 C5 H5 120.1 . . ? C4 C5 H5 120.1 . . ? C5 C6 C1 120.6(3) . . ? C5 C6 H6 119.7 . . ? C1 C6 H6 119.7 . . ? N1 C7 C1 123.4(3) . . ? N1 C7 H7 118.3 . . ? C1 C7 H7 118.3 . . ? N2 C8 O2 121.8(2) . . ? N2 C8 C9 122.3(2) . . ? O2 C8 C9 115.9(2) . . ? C10 C9 C14 116.3(3) . . ? C10 C9 C8 124.3(3) . . ? C14 C9 C8 119.4(3) . . ? F1 C10 C11 116.7(3) . . ? F1 C10 C9 120.4(3) . . ? C11 C10 C9 122.9(3) . . ? C12 C11 C10 118.7(3) . . ? C12 C11 H11 120.6 . . ? C10 C11 H11 120.6 . . ? C13 C12 C11 120.5(3) . . ? C13 C12 H12 119.7 . . ? C11 C12 H12 119.7 . . ? C12 C13 C14 120.3(3) . . ? C12 C13 H13 119.9 . . ? C14 C13 H13 119.9 . . ? C13 C14 C9 121.3(3) . . ? C13 C14 H14 119.4 . . ? C9 C14 H14 119.4 . . ? C16 C15 C20 119.5(3) . . ? C16 C15 C21 117.5(3) . . ? C20 C15 C21 122.9(3) . . ? C17 C16 C15 120.4(4) . . ? C17 C16 H16 119.8 . . ? C15 C16 H16 119.8 . . ? C16 C17 C18 119.8(4) . . ? C16 C17 H17 120.1 . . ? C18 C17 H17 120.1 . . ? C19 C18 C17 120.8(4) . . ? C19 C18 H18 119.6 . . ? C17 C18 H18 119.6 . . ? C18 C19 C20 120.2(4) . . ? C18 C19 H19 119.9 . . ? C20 C19 H19 119.9 . . ? C19 C20 C15 119.3(4) . . ? C19 C20 H20 120.3 . . ? C15 C20 H20 120.3 . . ? O3 C21 N3 117.2(3) . . ? O3 C21 C15 122.7(3) . . ? N3 C21 C15 120.1(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 N3 H3 F1 0.893(10) 2.29(3) 2.866(3) 122(2) 1_545 N3 H3 N2 0.893(10) 2.105(17) 2.915(3) 150(3) 1_545 _diffrn_measured_fraction_theta_max 0.997 _diffrn_reflns_theta_full 25.50 _diffrn_measured_fraction_theta_full 0.997 _refine_diff_density_max 0.854 _refine_diff_density_min -0.772 _refine_diff_density_rms 0.058