data_global _publ_contact_author_name 'Franc Perdih' _publ_contact_author_address ; Faculty of Chemistry and Chemical Technology University of Ljubljana Vecna pot 113, P. O. Box 537 1000 Ljubljana Slovenia ; _publ_contact_author_email franc.perdih@fkkt.uni-lj.si loop_ _publ_author_name _publ_author_address 'Tanja Kole\2\s(I) _computing_data_collection 'CrysAlis PRO (Agilent, 2011)' _computing_cell_refinement 'CrysAlis PRO (Agilent, 2011)' _computing_data_reduction 'CrysAlis PRO (Agilent, 2011)' _computing_structure_solution 'SIR2004 (Burla et al., 2005)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _computing_molecular_graphics ; ORTEP-3 (Farrugia, 1997) and DIAMOND (Brandenburg, 1999) ; _computing_publication_material 'WinGX publication routines (Farrugia, 1999)' _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^ > 2\s(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^)+(0.0585P)^2^+0.5922P] 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 constr _refine_ls_extinction_method SHELXL _refine_ls_extinction_coef 0.00093(17) _refine_ls_extinction_expression 'Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^' _refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _refine_ls_abs_structure_Flack 0.28(3) _refine_ls_number_reflns 1576 _refine_ls_number_parameters 241 _refine_ls_number_restraints 69 _refine_ls_R_factor_all 0.0468 _refine_ls_R_factor_gt 0.0393 _refine_ls_wR_factor_ref 0.1087 _refine_ls_wR_factor_gt 0.1007 _refine_ls_goodness_of_fit_ref 1.059 _refine_ls_restrained_S_all 1.091 _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 C1 C -0.09166(18) 0.23221(16) 0.4999(12) 0.0717(9) Uani 1 1 d D . . C2 C -0.09331(15) 0.14216(14) 0.5078(13) 0.0622(8) Uani 1 1 d . B . C4 C -0.17464(14) 0.02070(15) 0.5103(9) 0.0550(7) Uani 1 1 d D . . C3 C -0.16515(13) 0.10306(14) 0.5004(10) 0.0531(6) Uani 1 1 d . B . H3 H -0.2129 0.1342 0.4873 0.064 Uiso 1 1 calc R . . C5 C -0.25357(17) -0.01811(17) 0.4892(8) 0.0582(8) Uani 1 1 d D . . C6 C -0.25908(16) -0.09982(17) 0.5043(11) 0.0636(8) Uani 1 1 d D . . H6 H -0.2107 -0.1285 0.5290 0.076 Uiso 1 1 calc R A 1 F1A F -0.1438(9) 0.2592(6) 0.384(2) 0.136(8) Uani 0.53(2) 1 d PDU B 1 F2A F -0.1118(11) 0.2624(7) 0.6493(16) 0.138(7) Uani 0.53(2) 1 d PDU B 1 F3A F -0.0230(5) 0.2607(4) 0.468(3) 0.135(8) Uani 0.53(2) 1 d PDU B 1 F1B F -0.1618(5) 0.2628(5) 0.549(3) 0.138(10) Uani 0.47(2) 1 d PDU B 2 F2B F -0.0422(12) 0.2594(7) 0.618(3) 0.138(7) Uani 0.47(2) 1 d PDU B 2 F3B F -0.0656(17) 0.2617(8) 0.354(2) 0.172(10) Uani 0.47(2) 1 d PDU B 2 V1A V 0.0000 0.0000 0.6099(3) 0.0348(7) Uani 0.568(6) 2 d SPD . 1 O2A O -0.0248(3) 0.1140(3) 0.5673(10) 0.0492(17) Uani 0.568(6) 1 d P B 1 O3A O -0.1165(3) -0.0237(4) 0.5708(8) 0.0459(16) Uani 0.568(6) 1 d P . 1 O1A O 0.0000 0.0000 0.8230(15) 0.065(5) Uani 0.568(6) 2 d SPDU . 1 C10A C -0.3209(5) 0.0274(6) 0.4409(15) 0.064(3) Uani 0.568(6) 1 d PD . 1 H10A H -0.3178 0.0833 0.4233 0.077 Uiso 0.568(6) 1 calc PR . 1 C9A C -0.3943(5) -0.0158(9) 0.4199(16) 0.085(4) Uani 0.568(6) 1 d PD . 1 H9A H -0.4421 0.0136 0.3936 0.102 Uiso 0.568(6) 1 calc PR . 1 C8A C -0.4010(6) -0.0920(8) 0.434(2) 0.097(6) Uani 0.568(6) 1 d PD . 1 H8A H -0.4519 -0.1163 0.4104 0.116 Uiso 0.568(6) 1 calc PR . 1 C7A C -0.3308(10) -0.1431(13) 0.486(3) 0.101(7) Uani 0.568(6) 1 d PD . 1 H7A H -0.3346 -0.1989 0.5042 0.122 Uiso 0.568(6) 1 calc PR . 1 V1B V 0.0000 0.0000 0.3929(3) 0.0362(10) Uani 0.432(6) 2 d SPD . 2 O2B O -0.0249(4) 0.1147(4) 0.4284(12) 0.0422(16) Uani 0.432(6) 1 d P B 2 O3B O -0.1163(4) -0.0261(4) 0.4341(11) 0.0379(17) Uani 0.432(6) 1 d P . 2 O1B O 0.0000 0.0000 0.1787(19) 0.050(6) Uani 0.432(6) 2 d SPDU . 2 C7B C -0.3366(18) -0.1312(15) 0.534(5) 0.091(8) Uani 0.432(6) 1 d P . 2 H7B H -0.3422 -0.1867 0.5134 0.109 Uiso 0.432(6) 1 calc PR . 2 C8B C -0.4010(8) -0.0951(11) 0.586(2) 0.091(6) Uani 0.432(6) 1 d P . 2 H8B H -0.4498 -0.1237 0.6080 0.109 Uiso 0.432(6) 1 calc PR . 2 C9B C -0.3975(5) -0.0097(8) 0.610(3) 0.069(3) Uani 0.432(6) 1 d P . 2 H9B H -0.4431 0.0208 0.6462 0.083 Uiso 0.432(6) 1 calc PR . 2 C10B C -0.3256(6) 0.0224(8) 0.5763(11) 0.051(3) Uani 0.432(6) 1 d P . 2 H10B H -0.3184 0.0764 0.6105 0.062 Uiso 0.432(6) 1 calc PR . 2 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 C1 0.0589(15) 0.0401(13) 0.116(3) -0.003(4) 0.004(4) 0.0087(12) C2 0.0442(12) 0.0341(11) 0.108(2) -0.005(3) -0.004(3) 0.0061(9) C4 0.0322(10) 0.0459(12) 0.087(2) -0.007(3) 0.002(3) 0.0036(9) C3 0.0376(11) 0.0416(11) 0.0802(18) 0.000(3) -0.004(3) 0.0086(9) C5 0.0353(11) 0.0538(14) 0.085(2) -0.002(3) -0.005(2) -0.0021(10) C6 0.0472(13) 0.0578(14) 0.086(2) 0.006(4) -0.006(3) -0.0106(11) F1A 0.167(14) 0.063(5) 0.179(14) 0.046(7) -0.080(13) 0.005(6) F2A 0.183(18) 0.077(5) 0.153(8) -0.042(6) -0.015(10) 0.055(8) F3A 0.094(4) 0.043(3) 0.27(2) 0.035(7) 0.016(7) -0.010(3) F1B 0.064(4) 0.041(3) 0.31(3) -0.008(7) 0.052(9) 0.020(2) F2B 0.182(14) 0.059(6) 0.171(13) 0.006(8) -0.059(14) -0.060(8) F3B 0.27(3) 0.122(9) 0.127(9) 0.063(8) 0.039(15) -0.024(13) V1A 0.0300(8) 0.0409(11) 0.0334(17) 0.000 0.000 0.0025(7) O2A 0.035(2) 0.032(3) 0.081(6) -0.002(2) -0.003(2) 0.0049(19) O3A 0.039(3) 0.042(3) 0.057(5) 0.003(2) 0.002(2) -0.002(2) O1A 0.053(7) 0.072(8) 0.071(8) 0.000 0.000 0.009(5) C10A 0.030(3) 0.057(4) 0.105(9) 0.002(4) -0.001(3) 0.000(3) C9A 0.031(3) 0.118(10) 0.106(8) -0.008(6) -0.009(4) -0.017(4) C8A 0.042(5) 0.086(7) 0.163(18) -0.007(7) 0.002(6) -0.027(4) C7A 0.047(5) 0.081(11) 0.176(18) -0.027(11) -0.011(8) -0.025(6) V1B 0.0314(13) 0.0239(12) 0.053(2) 0.000 0.000 0.0048(9) O2B 0.041(3) 0.037(4) 0.049(5) -0.002(3) 0.011(3) -0.001(3) O3B 0.028(3) 0.035(4) 0.051(5) -0.003(3) -0.004(3) 0.000(2) O1B 0.038(6) 0.054(7) 0.058(11) 0.000 0.000 0.012(5) C7B 0.090(13) 0.035(4) 0.15(2) 0.008(9) 0.014(10) -0.019(5) C8B 0.042(6) 0.154(16) 0.077(9) 0.040(10) 0.009(7) -0.024(7) C9B 0.038(4) 0.071(7) 0.098(7) 0.000(7) 0.000(7) 0.013(5) C10B 0.036(4) 0.087(8) 0.031(6) 0.009(4) 0.001(3) 0.001(4) _geom_special_details ; All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell s.u.'s are taken into account individually in the estimation of s.u.'s in distances, angles and torsion angles; correlations between s.u.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell s.u.'s is used for estimating s.u.'s 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 C1 F3A 1.252(9) . ? C1 F2A 1.275(11) . ? C1 F3B 1.279(11) . ? C1 F2B 1.286(11) . ? C1 F1A 1.303(9) . ? C1 F1B 1.317(7) . ? C1 C2 1.515(3) . ? C2 O2A 1.303(7) . ? C2 C3 1.355(3) . ? C2 O2B 1.356(8) . ? C4 O3A 1.296(6) . ? C4 O3B 1.368(7) . ? C4 C3 1.395(4) . ? C4 C5 1.463(4) . ? C3 H3 0.9500 . ? C5 C6 1.381(4) . ? C5 C10A 1.395(9) . ? C5 C10B 1.516(11) . ? C6 C7A 1.395(15) . ? C6 C7B 1.40(3) . ? C6 H6 0.9500 . ? V1A O1A 1.601(11) . ? V1A O3A 1.982(5) . ? V1A O3A 1.982(5) 2 ? V1A O2A 1.985(5) . ? V1A O2A 1.985(5) 2 ? V1A O1A 2.155(11) 3_554 ? O1A V1A 2.155(11) 3 ? C10A C9A 1.420(12) . ? C10A H10A 0.9500 . ? C9A C8A 1.290(18) . ? C9A H9A 0.9500 . ? C8A C7A 1.49(3) . ? C8A H8A 0.9500 . ? C7A H7A 0.9500 . ? V1B O1B 1.609(13) . ? V1B O2B 1.989(7) 2 ? V1B O2B 1.989(7) . ? V1B O3B 1.990(6) 2 ? V1B O3B 1.990(6) . ? V1B O1B 2.147(13) 3 ? O1B V1B 2.147(13) 3_554 ? C7B C8B 1.28(3) . ? C7B H7B 0.9500 . ? C8B C9B 1.45(2) . ? C8B H8B 0.9500 . ? C9B C10B 1.327(15) . ? C9B H9B 0.9500 . ? C10B H10B 0.9500 . ? 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 F3A C1 F2A 104.6(13) . . ? F3A C1 F3B 52.0(12) . . ? F2A C1 F3B 133.5(10) . . ? F3A C1 F2B 54.8(11) . . ? F2A C1 F2B 54.4(10) . . ? F3B C1 F2B 103.9(11) . . ? F3A C1 F1A 109.5(11) . . ? F2A C1 F1A 106.1(9) . . ? F3B C1 F1A 60.8(14) . . ? F2B C1 F1A 138.8(8) . . ? F3A C1 F1B 134.2(6) . . ? F2A C1 F1B 51.0(10) . . ? F3B C1 F1B 112.5(14) . . ? F2B C1 F1B 103.0(14) . . ? F1A C1 F1B 58.2(9) . . ? F3A C1 C2 113.9(4) . . ? F2A C1 C2 111.0(8) . . ? F3B C1 C2 115.3(9) . . ? F2B C1 C2 109.9(7) . . ? F1A C1 C2 111.2(6) . . ? F1B C1 C2 111.3(5) . . ? O2A C2 C3 126.5(4) . . ? O2A C2 O2B 46.1(2) . . ? C3 C2 O2B 122.9(5) . . ? O2A C2 C1 111.2(4) . . ? C3 C2 C1 119.9(2) . . ? O2B C2 C1 107.9(4) . . ? O3A C4 O3B 45.3(2) . . ? O3A C4 C3 120.5(4) . . ? O3B C4 C3 118.0(4) . . ? O3A C4 C5 115.9(4) . . ? O3B C4 C5 108.8(4) . . ? C3 C4 C5 122.4(2) . . ? C2 C3 C4 125.3(2) . . ? C2 C3 H3 117.4 . . ? C4 C3 H3 117.4 . . ? C6 C5 C10A 121.0(4) . . ? C6 C5 C4 119.5(3) . . ? C10A C5 C4 119.3(4) . . ? C6 C5 C10B 111.1(5) . . ? C4 C5 C10B 116.6(5) . . ? C5 C6 C7A 124.5(11) . . ? C5 C6 C7B 116.6(12) . . ? C5 C6 H6 117.8 . . ? C7A C6 H6 117.8 . . ? C7B C6 H6 122.9 . . ? O1A V1A O3A 98.5(2) . . ? O1A V1A O3A 98.5(2) . 2 ? O3A V1A O3A 162.9(4) . 2 ? O1A V1A O2A 99.3(2) . . ? O3A V1A O2A 88.3(2) . . ? O3A V1A O2A 88.9(2) 2 . ? O1A V1A O2A 99.3(2) . 2 ? O3A V1A O2A 88.9(2) . 2 ? O3A V1A O2A 88.3(2) 2 2 ? O2A V1A O2A 161.4(5) . 2 ? O1A V1A O1A 180.000(4) . 3_554 ? O3A V1A O1A 81.5(2) . 3_554 ? O3A V1A O1A 81.5(2) 2 3_554 ? O2A V1A O1A 80.7(2) . 3_554 ? O2A V1A O1A 80.7(2) 2 3_554 ? C2 O2A V1A 125.8(4) . . ? C4 O3A V1A 130.6(4) . . ? V1A O1A V1A 180.000(1) . 3 ? C5 C10A C9A 115.1(8) . . ? C5 C10A H10A 122.4 . . ? C9A C10A H10A 122.4 . . ? C8A C9A C10A 124.8(10) . . ? C8A C9A H9A 117.6 . . ? C10A C9A H9A 117.6 . . ? C9A C8A C7A 121.8(10) . . ? C9A C8A H8A 119.1 . . ? C7A C8A H8A 119.1 . . ? C6 C7A C8A 112.5(16) . . ? C6 C7A H7A 123.8 . . ? C8A C7A H7A 123.8 . . ? O1B V1B O2B 97.7(3) . 2 ? O1B V1B O2B 97.7(3) . . ? O2B V1B O2B 164.6(6) 2 . ? O1B V1B O3B 99.0(3) . 2 ? O2B V1B O3B 89.7(3) 2 2 ? O2B V1B O3B 87.9(3) . 2 ? O1B V1B O3B 99.0(3) . . ? O2B V1B O3B 87.9(3) 2 . ? O2B V1B O3B 89.7(3) . . ? O3B V1B O3B 162.1(5) 2 . ? O1B V1B O1B 180.000(2) . 3 ? O2B V1B O1B 82.3(3) 2 3 ? O2B V1B O1B 82.3(3) . 3 ? O3B V1B O1B 81.0(3) 2 3 ? O3B V1B O1B 81.0(3) . 3 ? C2 O2B V1B 124.1(5) . . ? C4 O3B V1B 127.9(4) . . ? V1B O1B V1B 180.0 . 3_554 ? C8B C7B C6 129(2) . . ? C8B C7B H7B 115.7 . . ? C6 C7B H7B 115.7 . . ? C7B C8B C9B 118.3(14) . . ? C7B C8B H8B 120.9 . . ? C9B C8B H8B 120.9 . . ? C10B C9B C8B 114.6(11) . . ? C10B C9B H9B 122.7 . . ? C8B C9B H9B 122.7 . . ? C9B C10B C5 126.7(11) . . ? C9B C10B H10B 116.7 . . ? C5 C10B H10B 116.7 . . ? 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 F3A C1 C2 O2A 31.8(16) . . . . ? F2A C1 C2 O2A -85.9(11) . . . . ? F3B C1 C2 O2A 89.4(17) . . . . ? F2B C1 C2 O2A -27.5(15) . . . . ? F1A C1 C2 O2A 156.1(12) . . . . ? F1B C1 C2 O2A -140.9(13) . . . . ? F3A C1 C2 C3 -164.8(14) . . . . ? F2A C1 C2 C3 77.4(12) . . . . ? F3B C1 C2 C3 -107.2(16) . . . . ? F2B C1 C2 C3 135.8(13) . . . . ? F1A C1 C2 C3 -40.5(13) . . . . ? F1B C1 C2 C3 22.4(16) . . . . ? F3A C1 C2 O2B -17.2(16) . . . . ? F2A C1 C2 O2B -135.0(10) . . . . ? F3B C1 C2 O2B 40.4(17) . . . . ? F2B C1 C2 O2B -76.6(14) . . . . ? F1A C1 C2 O2B 107.1(12) . . . . ? F1B C1 C2 O2B 170.0(13) . . . . ? O2A C2 C3 C4 -17.9(14) . . . . ? O2B C2 C3 C4 38.8(13) . . . . ? C1 C2 C3 C4 -178.5(7) . . . . ? O3A C4 C3 C2 17.0(11) . . . . ? O3B C4 C3 C2 -35.3(11) . . . . ? C5 C4 C3 C2 -175.7(7) . . . . ? O3A C4 C5 C6 -10.8(7) . . . . ? O3B C4 C5 C6 37.9(6) . . . . ? C3 C4 C5 C6 -178.6(6) . . . . ? O3A C4 C5 C10A 174.0(7) . . . . ? O3B C4 C5 C10A -137.4(7) . . . . ? C3 C4 C5 C10A 6.1(8) . . . . ? O3A C4 C5 C10B 127.5(6) . . . . ? O3B C4 C5 C10B 176.1(6) . . . . ? C3 C4 C5 C10B -40.4(8) . . . . ? C10A C5 C6 C7A -4.5(14) . . . . ? C4 C5 C6 C7A -179.6(12) . . . . ? C10B C5 C6 C7A 40.0(13) . . . . ? C10A C5 C6 C7B -22.7(19) . . . . ? C4 C5 C6 C7B 162.1(18) . . . . ? C10B C5 C6 C7B 21.8(18) . . . . ? C3 C2 O2A V1A 15.4(13) . . . . ? O2B C2 O2A V1A -87.7(8) . . . . ? C1 C2 O2A V1A 177.4(5) . . . . ? O1A V1A O2A C2 -108.1(7) . . . . ? O3A V1A O2A C2 -9.7(8) . . . . ? O3A V1A O2A C2 153.4(7) 2 . . . ? O2A V1A O2A C2 71.9(7) 2 . . . ? O1A V1A O2A C2 71.9(7) 3_554 . . . ? O3B C4 O3A V1A 85.3(7) . . . . ? C3 C4 O3A V1A -15.3(9) . . . . ? C5 C4 O3A V1A 176.6(4) . . . . ? O1A V1A O3A C4 109.8(6) . . . . ? O3A V1A O3A C4 -70.2(6) 2 . . . ? O2A V1A O3A C4 10.6(7) . . . . ? O2A V1A O3A C4 -151.0(6) 2 . . . ? O1A V1A O3A C4 -70.2(6) 3_554 . . . ? C6 C5 C10A C9A 3.5(12) . . . . ? C4 C5 C10A C9A 178.7(7) . . . . ? C10B C5 C10A C9A -83.5(13) . . . . ? C5 C10A C9A C8A -3.5(18) . . . . ? C10A C9A C8A C7A 4(2) . . . . ? C5 C6 C7A C8A 4(2) . . . . ? C7B C6 C7A C8A 73(7) . . . . ? C9A C8A C7A C6 -4(2) . . . . ? O2A C2 O2B V1B 80.7(8) . . . . ? C3 C2 O2B V1B -30.4(12) . . . . ? C1 C2 O2B V1B -176.9(6) . . . . ? O1B V1B O2B C2 116.4(7) . . . . ? O2B V1B O2B C2 -63.6(7) 2 . . . ? O3B V1B O2B C2 -144.9(8) 2 . . . ? O3B V1B O2B C2 17.4(8) . . . . ? O1B V1B O2B C2 -63.6(7) 3 . . . ? O3A C4 O3B V1B -80.0(7) . . . . ? C3 C4 O3B V1B 26.4(9) . . . . ? C5 C4 O3B V1B 171.7(5) . . . . ? O1B V1B O3B C4 -114.5(6) . . . . ? O2B V1B O3B C4 148.0(6) 2 . . . ? O2B V1B O3B C4 -16.7(7) . . . . ? O3B V1B O3B C4 65.5(6) 2 . . . ? O1B V1B O3B C4 65.5(6) 3 . . . ? C5 C6 C7B C8B -16(4) . . . . ? C7A C6 C7B C8B -137(10) . . . . ? C6 C7B C8B C9B 4(4) . . . . ? C7B C8B C9B C10B -1(3) . . . . ? C8B C9B C10B C5 11(2) . . . . ? C6 C5 C10B C9B -21.9(13) . . . . ? C10A C5 C10B C9B 91.5(16) . . . . ? C4 C5 C10B C9B -163.5(11) . . . . ? _diffrn_measured_fraction_theta_max 0.986 _diffrn_reflns_theta_full 74.73 _diffrn_measured_fraction_theta_full 0.985 _refine_diff_density_max 0.180 _refine_diff_density_min -0.199 _refine_diff_density_rms 0.039 #===END data_1b _audit_creation_method SHELXL-97 _chemical_name_systematic ; bis(4,4,4-trifluoro-1-phenylbutane-1,3-dionato)oxidovanadium(IV) ; _chemical_name_common ; bis(4,4,4-trifluoro-1-phenylbutane-1,3-dionato)oxidovanadium(IV) ; _chemical_melting_point ? _chemical_formula_moiety 'C20 H12 F6 O5 V' _chemical_formula_sum 'C20 H12 F6 O5 V' _chemical_formula_weight 497.24 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' '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' _symmetry_cell_setting orthorhombic _symmetry_space_group_name_H-M Ccc2 _symmetry_space_group_name_Hall 'C 2 -2c' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, z' '-x, y, z+1/2' 'x, -y, z+1/2' 'x+1/2, y+1/2, z' '-x+1/2, -y+1/2, z' '-x+1/2, y+1/2, z+1/2' 'x+1/2, -y+1/2, z+1/2' _cell_length_a 16.7507(10) _cell_length_b 16.8587(14) _cell_length_c 7.5561(6) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 2133.8(3) _cell_formula_units_Z 4 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 1765 _cell_measurement_theta_min 3.1885 _cell_measurement_theta_max 30.3045 _exptl_crystal_description needle _exptl_crystal_colour yellow _exptl_crystal_size_max 0.25 _exptl_crystal_size_mid 0.05 _exptl_crystal_size_min 0.05 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.548 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 996 _exptl_absorpt_coefficient_mu 0.545 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.8757 _exptl_absorpt_correction_T_max 0.9732 _exptl_absorpt_process_details '(CrysAlis PRO; Agilent, 2011)' _exptl_special_details ; 213 frames in 3 runs of \w scans. Crystal-detector distance = 55.0 mm. ; _diffrn_ambient_temperature 293(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'SuperNova (Mo) X-ray Source' _diffrn_radiation_monochromator Mirror _diffrn_measurement_device_type 'SuperNova, Dual, Cu at zero, Atlas' _diffrn_measurement_method '\w scans' _diffrn_detector_area_resol_mean 10.4933 _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 5510 _diffrn_reflns_av_R_equivalents 0.0402 _diffrn_reflns_av_sigmaI/netI 0.0348 _diffrn_reflns_limit_h_min -21 _diffrn_reflns_limit_h_max 20 _diffrn_reflns_limit_k_min -21 _diffrn_reflns_limit_k_max 18 _diffrn_reflns_limit_l_min -9 _diffrn_reflns_limit_l_max 6 _diffrn_reflns_theta_min 3.19 _diffrn_reflns_theta_max 27.47 _reflns_number_total 1929 _reflns_number_gt 1340 _reflns_threshold_expression >2\s(I) _computing_data_collection 'CrysAlis PRO (Agilent, 2011)' _computing_cell_refinement 'CrysAlis PRO (Agilent, 2011)' _computing_data_reduction 'CrysAlis PRO (Agilent, 2011)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 2008)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _computing_molecular_graphics ; ORTEP-3 (Farrugia, 1997) and DIAMOND (Brandenburg, 1999) ; _computing_publication_material 'WinGX publication routines (Farrugia, 1999)' _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^ > 2\s(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^)+(0.0483P)^2^+0.3845P] 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 constr _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _refine_ls_abs_structure_Flack -0.03(9) _refine_ls_number_reflns 1929 _refine_ls_number_parameters 234 _refine_ls_number_restraints 38 _refine_ls_R_factor_all 0.0808 _refine_ls_R_factor_gt 0.0533 _refine_ls_wR_factor_ref 0.1295 _refine_ls_wR_factor_gt 0.1139 _refine_ls_goodness_of_fit_ref 1.104 _refine_ls_restrained_S_all 1.123 _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 C1 C 0.9048(3) 0.2302(3) 0.5122(15) 0.1039(16) Uani 1 1 d D . . F1A F 0.8792(18) 0.2517(10) 0.359(3) 0.245(12) Uani 0.53(2) 1 d PDU A 1 F2A F 0.8544(15) 0.2571(7) 0.632(3) 0.201(11) Uani 0.53(2) 1 d PD A 1 F3A F 0.9710(6) 0.2613(6) 0.542(4) 0.171(12) Uani 0.53(2) 1 d PD A 1 F1B F 0.8352(5) 0.2602(6) 0.478(4) 0.147(10) Uani 0.47(2) 1 d PDU A 2 F2B F 0.9285(15) 0.2635(8) 0.660(3) 0.162(11) Uani 0.47(2) 1 d PD A 2 F3B F 0.9527(12) 0.2581(9) 0.391(3) 0.149(8) Uani 0.47(2) 1 d PD A 2 C2 C 0.90498(18) 0.14080(19) 0.5225(13) 0.0725(10) Uani 1 1 d . A . C4 C 0.82711(17) 0.0189(2) 0.5254(12) 0.0648(9) Uani 1 1 d . . . C3 C 0.83498(17) 0.1011(2) 0.5218(14) 0.0745(10) Uani 1 1 d . A . H3 H 0.7884 0.1310 0.5187 0.089 Uiso 1 1 calc R . . C5 C 0.74927(19) -0.0211(2) 0.5171(16) 0.0777(10) Uani 1 1 d . . . C6 C 0.7452(2) -0.1015(3) 0.5227(16) 0.0957(13) Uani 1 1 d . . . H6 H 0.7907 -0.1317 0.5436 0.115 Uiso 1 1 calc R B 1 V1A V 1.0000 0.0000 0.6131(3) 0.0422(9) Uani 0.566(8) 2 d SP . 1 O2A O 0.9745(8) 0.1128(6) 0.5747(17) 0.060(2) Uani 0.566(8) 1 d P A 1 O3A O 0.8850(6) -0.0261(5) 0.5801(17) 0.0542(19) Uani 0.566(8) 1 d P . 1 O1A O 1.0000 0.0000 0.817(3) 0.077(7) Uani 0.566(8) 2 d SP . 1 C10A C 0.6835(7) 0.0222(8) 0.472(2) 0.078(4) Uani 0.566(8) 1 d P . 1 H10A H 0.6862 0.0767 0.4545 0.093 Uiso 0.566(8) 1 calc PR . 1 C9A C 0.6118(10) -0.0196(14) 0.455(4) 0.140(8) Uani 0.566(8) 1 d P . 1 H9A H 0.5654 0.0094 0.4356 0.168 Uiso 0.566(8) 1 calc PR . 1 C8A C 0.6059(11) -0.0965(15) 0.464(4) 0.142(9) Uani 0.566(8) 1 d P . 1 H8A H 0.5569 -0.1214 0.4477 0.171 Uiso 0.566(8) 1 calc PR . 1 C7A C 0.6703(8) -0.1383(8) 0.496(3) 0.096(5) Uani 0.566(8) 1 d P . 1 H7A H 0.6666 -0.1933 0.5016 0.115 Uiso 0.566(8) 1 calc PR . 1 V1B V 1.0000 0.0000 0.4269(7) 0.0530(18) Uani 0.434(8) 2 d SP . 2 O2B O 0.9726(11) 0.1139(8) 0.474(2) 0.063(3) Uani 0.434(8) 1 d P A 2 O3B O 0.8874(8) -0.0279(8) 0.480(2) 0.063(3) Uani 0.434(8) 1 d P . 2 O1B O 1.0000 0.0000 0.223(4) 0.094(9) Uani 0.434(8) 2 d SP . 2 C7B C 0.6759(18) -0.1439(18) 0.570(5) 0.146(12) Uiso 0.434(8) 1 d P . 2 H7B H 0.6759 -0.1988 0.5813 0.176 Uiso 0.434(8) 1 calc PR . 2 C8B C 0.6037(12) -0.0965(18) 0.601(5) 0.128(9) Uani 0.434(8) 1 d P . 2 H8B H 0.5548 -0.1223 0.6085 0.154 Uiso 0.434(8) 1 calc PR . 2 C9B C 0.6059(8) -0.0147(10) 0.620(4) 0.086(4) Uani 0.434(8) 1 d P . 2 H9B H 0.5605 0.0145 0.6487 0.104 Uiso 0.434(8) 1 calc PR . 2 C10B C 0.6748(9) 0.0191(11) 0.597(3) 0.091(5) Uani 0.434(8) 1 d P . 2 H10B H 0.6797 0.0719 0.6306 0.110 Uiso 0.434(8) 1 calc PR . 2 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 C1 0.088(3) 0.054(3) 0.170(5) -0.008(6) 0.024(8) 0.008(2) F1A 0.28(3) 0.183(13) 0.269(18) 0.133(13) -0.106(19) -0.082(14) F2A 0.27(2) 0.057(6) 0.27(3) -0.049(10) 0.100(19) 0.030(11) F3A 0.123(6) 0.048(4) 0.34(4) -0.024(12) 0.020(13) -0.018(3) F1B 0.069(5) 0.059(5) 0.31(3) 0.050(9) -0.007(8) 0.022(3) F2B 0.19(2) 0.079(7) 0.213(19) -0.073(10) -0.045(18) 0.004(13) F3B 0.149(13) 0.096(8) 0.202(19) 0.040(10) 0.030(14) -0.038(7) C2 0.0609(18) 0.049(2) 0.108(3) -0.009(4) -0.020(4) 0.0078(14) C4 0.0518(16) 0.064(2) 0.079(2) 0.006(3) -0.005(4) 0.0005(13) C3 0.0535(17) 0.054(2) 0.116(3) 0.009(4) 0.007(4) 0.0087(14) C5 0.0555(18) 0.072(2) 0.106(3) 0.001(4) -0.007(4) -0.0097(15) C6 0.074(2) 0.083(3) 0.131(4) 0.006(6) -0.003(5) -0.0181(19) V1A 0.0514(13) 0.0400(11) 0.0352(16) 0.000 0.000 -0.0002(8) O2A 0.053(5) 0.043(4) 0.084(6) 0.002(6) -0.019(7) 0.001(3) O3A 0.050(4) 0.042(4) 0.070(5) 0.002(5) 0.012(6) -0.003(2) O1A 0.107(14) 0.074(8) 0.049(15) 0.000 0.000 0.031(7) C10A 0.042(5) 0.078(7) 0.114(12) -0.010(7) -0.005(6) 0.002(4) C9A 0.065(8) 0.20(2) 0.16(2) -0.008(14) -0.006(8) -0.028(9) C8A 0.082(11) 0.149(17) 0.20(2) -0.076(18) -0.019(12) -0.024(10) C7A 0.086(7) 0.070(6) 0.131(16) -0.002(8) -0.015(8) -0.045(5) V1B 0.0349(17) 0.055(2) 0.069(4) 0.000 0.000 0.0099(12) O2B 0.058(7) 0.051(6) 0.080(7) 0.000(7) -0.012(9) -0.001(4) O3B 0.052(6) 0.065(6) 0.073(7) -0.005(7) 0.008(7) 0.005(4) O1B 0.068(11) 0.159(19) 0.056(17) 0.000 0.000 -0.013(9) C8B 0.069(12) 0.18(3) 0.134(14) -0.02(2) -0.006(14) -0.074(13) C9B 0.041(6) 0.108(14) 0.110(14) 0.011(11) -0.002(9) -0.004(7) C10B 0.058(8) 0.138(14) 0.079(9) -0.014(13) 0.012(11) -0.014(7) _geom_special_details ; All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell s.u.'s are taken into account individually in the estimation of s.u.'s in distances, angles and torsion angles; correlations between s.u.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell s.u.'s is used for estimating s.u.'s 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 C1 F3A 1.247(10) . ? C1 F1A 1.287(13) . ? C1 F1B 1.297(9) . ? C1 F3B 1.306(11) . ? C1 F2B 1.309(12) . ? C1 F2A 1.317(11) . ? C1 C2 1.509(5) . ? C2 O2B 1.273(19) . ? C2 O2A 1.317(13) . ? C2 C3 1.350(4) . ? C4 O3A 1.299(10) . ? C4 O3B 1.327(14) . ? C4 C3 1.392(5) . ? C4 C5 1.470(4) . ? C3 H3 0.9300 . ? C5 C6 1.357(5) . ? C5 C10A 1.364(12) . ? C5 C10B 1.541(19) . ? C6 C7B 1.41(3) . ? C6 C7A 1.414(12) . ? C6 H6 0.9300 . ? V1A O1A 1.54(2) . ? V1A O2A 1.970(10) 2_755 ? V1A O2A 1.970(10) . ? V1A O3A 1.992(9) . ? V1A O3A 1.992(9) 2_755 ? V1A O1A 2.23(2) 3_754 ? O1A V1A 2.23(2) 3_755 ? C10A C9A 1.40(2) . ? C10A H10A 0.9300 . ? C9A C8A 1.30(3) . ? C9A H9A 0.9300 . ? C8A C7A 1.31(3) . ? C8A H8A 0.9300 . ? C7A H7A 0.9300 . ? V1B O1B 1.54(3) . ? V1B O3B 1.984(14) 2_755 ? V1B O3B 1.984(14) . ? V1B O2B 2.007(15) 2_755 ? V1B O2B 2.007(15) . ? V1B O1B 2.24(3) 3_755 ? O1B V1B 2.24(3) 3_754 ? C7B C8B 1.47(4) . ? C7B H7B 0.9300 . ? C8B C9B 1.39(3) . ? C8B H8B 0.9300 . ? C9B C10B 1.30(2) . ? C9B H9B 0.9300 . ? C10B H10B 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 F3A C1 F1A 109.9(10) . . ? F3A C1 F1B 132.1(8) . . ? F1A C1 F1B 54.0(11) . . ? F3A C1 F3B 55.1(10) . . ? F1A C1 F3B 58.1(11) . . ? F1B C1 F3B 105.8(12) . . ? F3A C1 F2B 52.8(10) . . ? F1A C1 F2B 138.2(12) . . ? F1B C1 F2B 106.0(9) . . ? F3B C1 F2B 104.8(9) . . ? F3A C1 F2A 107.5(10) . . ? F1A C1 F2A 107.8(9) . . ? F1B C1 F2A 54.9(9) . . ? F3B C1 F2A 138.7(9) . . ? F2B C1 F2A 57.5(10) . . ? F3A C1 C2 114.1(6) . . ? F1A C1 C2 109.2(10) . . ? F1B C1 C2 113.7(6) . . ? F3B C1 C2 113.2(9) . . ? F2B C1 C2 112.6(10) . . ? F2A C1 C2 108.1(8) . . ? O2B C2 C3 126.5(8) . . ? O2A C2 C3 126.2(6) . . ? O2B C2 C1 110.0(8) . . ? O2A C2 C1 112.1(6) . . ? C3 C2 C1 119.5(3) . . ? O3A C4 C3 121.1(5) . . ? O3B C4 C3 121.0(7) . . ? O3A C4 C5 114.1(5) . . ? O3B C4 C5 113.1(7) . . ? C3 C4 C5 122.7(3) . . ? C2 C3 C4 125.1(3) . . ? C2 C3 H3 117.4 . . ? C4 C3 H3 117.4 . . ? C6 C5 C10A 120.1(6) . . ? C6 C5 C4 120.1(3) . . ? C10A C5 C4 118.8(6) . . ? C6 C5 C10B 112.7(8) . . ? C4 C5 C10B 120.0(8) . . ? C5 C6 C7B 123.8(14) . . ? C5 C6 C7A 118.6(8) . . ? C5 C6 H6 120.7 . . ? C7B C6 H6 110.7 . . ? C7A C6 H6 120.7 . . ? O1A V1A O2A 98.5(4) . 2_755 ? O1A V1A O2A 98.5(4) . . ? O2A V1A O2A 163.1(8) 2_755 . ? O1A V1A O3A 97.2(4) . . ? O2A V1A O3A 88.7(5) 2_755 . ? O2A V1A O3A 89.1(5) . . ? O1A V1A O3A 97.2(4) . 2_755 ? O2A V1A O3A 89.1(5) 2_755 2_755 ? O2A V1A O3A 88.7(5) . 2_755 ? O3A V1A O3A 165.7(8) . 2_755 ? O1A V1A O1A 180.000(7) . 3_754 ? O2A V1A O1A 81.5(4) 2_755 3_754 ? O2A V1A O1A 81.5(4) . 3_754 ? O3A V1A O1A 82.8(4) . 3_754 ? O3A V1A O1A 82.8(4) 2_755 3_754 ? C2 O2A V1A 125.6(8) . . ? C4 O3A V1A 129.2(6) . . ? V1A O1A V1A 180.000(1) . 3_755 ? C5 C10A C9A 116.6(13) . . ? C5 C10A H10A 121.7 . . ? C9A C10A H10A 121.7 . . ? C8A C9A C10A 124.1(18) . . ? C8A C9A H9A 117.9 . . ? C10A C9A H9A 117.9 . . ? C9A C8A C7A 118.9(17) . . ? C9A C8A H8A 120.6 . . ? C7A C8A H8A 120.6 . . ? C8A C7A C6 121.4(14) . . ? C8A C7A H7A 119.3 . . ? C6 C7A H7A 119.3 . . ? O1B V1B O3B 101.7(6) . 2_755 ? O1B V1B O3B 101.7(6) . . ? O3B V1B O3B 156.6(12) 2_755 . ? O1B V1B O2B 100.3(6) . 2_755 ? O3B V1B O2B 88.5(7) 2_755 2_755 ? O3B V1B O2B 87.4(6) . 2_755 ? O1B V1B O2B 100.3(6) . . ? O3B V1B O2B 87.4(6) 2_755 . ? O3B V1B O2B 88.5(7) . . ? O2B V1B O2B 159.4(12) 2_755 . ? O1B V1B O1B 180.000(4) . 3_755 ? O3B V1B O1B 78.3(6) 2_755 3_755 ? O3B V1B O1B 78.3(6) . 3_755 ? O2B V1B O1B 79.7(6) 2_755 3_755 ? O2B V1B O1B 79.7(6) . 3_755 ? C2 O2B V1B 126.5(11) . . ? C4 O3B V1B 129.4(9) . . ? V1B O1B V1B 180.000(1) . 3_754 ? C6 C7B C8B 116(2) . . ? C6 C7B H7B 121.9 . . ? C8B C7B H7B 121.9 . . ? C9B C8B C7B 122.4(16) . . ? C9B C8B H8B 118.8 . . ? C7B C8B H8B 118.8 . . ? C10B C9B C8B 116.3(16) . . ? C10B C9B H9B 121.8 . . ? C8B C9B H9B 121.8 . . ? C9B C10B C5 125.5(17) . . ? C9B C10B H10B 117.3 . . ? C5 C10B H10B 117.3 . . ? 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 F3A C1 C2 O2B -32(2) . . . . ? F1A C1 C2 O2B 91.7(19) . . . . ? F1B C1 C2 O2B 149.9(16) . . . . ? F3B C1 C2 O2B 29.1(17) . . . . ? F2B C1 C2 O2B -89.6(17) . . . . ? F2A C1 C2 O2B -151.2(17) . . . . ? F3A C1 C2 O2A 4.8(19) . . . . ? F1A C1 C2 O2A 128.2(18) . . . . ? F1B C1 C2 O2A -173.6(16) . . . . ? F3B C1 C2 O2A 65.6(16) . . . . ? F2B C1 C2 O2A -53.1(16) . . . . ? F2A C1 C2 O2A -114.7(17) . . . . ? F3A C1 C2 C3 169.1(17) . . . . ? F1A C1 C2 C3 -67.5(18) . . . . ? F1B C1 C2 C3 -9.3(18) . . . . ? F3B C1 C2 C3 -130.1(14) . . . . ? F2B C1 C2 C3 111.2(15) . . . . ? F2A C1 C2 C3 49.6(17) . . . . ? O2B C2 C3 C4 22.5(18) . . . . ? O2A C2 C3 C4 -20.1(16) . . . . ? C1 C2 C3 C4 178.0(9) . . . . ? O3A C4 C3 C2 20.1(15) . . . . ? O3B C4 C3 C2 -19.2(16) . . . . ? C5 C4 C3 C2 -177.4(9) . . . . ? O3A C4 C5 C6 -15.8(12) . . . . ? O3B C4 C5 C6 20.9(14) . . . . ? C3 C4 C5 C6 -179.4(9) . . . . ? O3A C4 C5 C10A 175.8(11) . . . . ? O3B C4 C5 C10A -147.6(13) . . . . ? C3 C4 C5 C10A 12.1(15) . . . . ? O3A C4 C5 C10B 132.3(12) . . . . ? O3B C4 C5 C10B 169.0(14) . . . . ? C3 C4 C5 C10B -31.3(16) . . . . ? C10A C5 C6 C7B -32(2) . . . . ? C4 C5 C6 C7B 159.5(18) . . . . ? C10B C5 C6 C7B 9(2) . . . . ? C10A C5 C6 C7A -5.2(18) . . . . ? C4 C5 C6 C7A -173.6(14) . . . . ? C10B C5 C6 C7A 36.2(18) . . . . ? O2B C2 O2A V1A -88(2) . . . . ? C3 C2 O2A V1A 15.0(17) . . . . ? C1 C2 O2A V1A 178.1(7) . . . . ? O1A V1A O2A C2 -105.4(10) . . . . ? O2A V1A O2A C2 74.6(10) 2_755 . . . ? O3A V1A O2A C2 -8.3(12) . . . . ? O3A V1A O2A C2 157.5(10) 2_755 . . . ? O1A V1A O2A C2 74.6(10) 3_754 . . . ? O3B C4 O3A V1A 83.9(18) . . . . ? C3 C4 O3A V1A -16.3(15) . . . . ? C5 C4 O3A V1A 179.8(9) . . . . ? O1A V1A O3A C4 108.2(10) . . . . ? O2A V1A O3A C4 -153.5(10) 2_755 . . . ? O2A V1A O3A C4 9.7(12) . . . . ? O3A V1A O3A C4 -71.8(10) 2_755 . . . ? O1A V1A O3A C4 -71.8(10) 3_754 . . . ? C6 C5 C10A C9A 7(2) . . . . ? C4 C5 C10A C9A 175.9(16) . . . . ? C10B C5 C10A C9A -81(2) . . . . ? C5 C10A C9A C8A -6(4) . . . . ? C10A C9A C8A C7A 2(5) . . . . ? C9A C8A C7A C6 1(4) . . . . ? C5 C6 C7A C8A 1(3) . . . . ? C7B C6 C7A C8A 111(5) . . . . ? O2A C2 O2B V1B 90(2) . . . . ? C3 C2 O2B V1B -12(2) . . . . ? C1 C2 O2B V1B -169.8(10) . . . . ? O1B V1B O2B C2 103.1(14) . . . . ? O3B V1B O2B C2 -155.4(12) 2_755 . . . ? O3B V1B O2B C2 1.5(17) . . . . ? O2B V1B O2B C2 -76.9(14) 2_755 . . . ? O1B V1B O2B C2 -76.9(14) 3_755 . . . ? O3A C4 O3B V1B -93(2) . . . . ? C3 C4 O3B V1B 8(2) . . . . ? C5 C4 O3B V1B 167.7(12) . . . . ? O1B V1B O3B C4 -99.8(15) . . . . ? O3B V1B O3B C4 80.2(15) 2_755 . . . ? O2B V1B O3B C4 160.2(14) 2_755 . . . ? O2B V1B O3B C4 0.4(18) . . . . ? O1B V1B O3B C4 80.2(15) 3_755 . . . ? C5 C6 C7B C8B 5(3) . . . . ? C7A C6 C7B C8B -80(5) . . . . ? C6 C7B C8B C9B -13(5) . . . . ? C7B C8B C9B C10B 5(5) . . . . ? C8B C9B C10B C5 12(4) . . . . ? C6 C5 C10B C9B -19(3) . . . . ? C10A C5 C10B C9B 91(3) . . . . ? C4 C5 C10B C9B -169(2) . . . . ? _diffrn_measured_fraction_theta_max 0.984 _diffrn_reflns_theta_full 27.47 _diffrn_measured_fraction_theta_full 0.984 _refine_diff_density_max 0.132 _refine_diff_density_min -0.187 _refine_diff_density_rms 0.033 #===END data_2 _audit_creation_method SHELXL-97 _chemical_name_systematic ; bis(pentane-2,4-dionato-\k^2^O,O')(2-pyridone-\kO)oxidovanadium(IV) ; _chemical_name_common ; bis(acetylacetonato)(2-pyridone)oxidovanadium(IV) ; _chemical_melting_point ? _chemical_formula_moiety 'C10 H14 O5 V, C5 H5 N O' _chemical_formula_sum 'C15 H19 N O6 V' _chemical_formula_weight 360.25 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' 'V' 'V' 0.3005 0.5294 '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 7.5066(3) _cell_length_b 10.6366(6) _cell_length_c 10.7430(5) _cell_angle_alpha 88.063(3) _cell_angle_beta 75.206(3) _cell_angle_gamma 85.574(3) _cell_volume 826.78(7) _cell_formula_units_Z 2 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 3588 _cell_measurement_theta_min 1.00 _cell_measurement_theta_max 27.48 _exptl_crystal_description prism _exptl_crystal_colour green _exptl_crystal_size_max 0.20 _exptl_crystal_size_mid 0.10 _exptl_crystal_size_min 0.08 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.447 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 374 _exptl_absorpt_coefficient_mu 0.629 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.8846 _exptl_absorpt_correction_T_max 0.9514 _exptl_absorpt_process_details 'SCALEPACK (Otwinowski & Minor, 1997)' _exptl_special_details ; 190 frames in 6 sets of \w scans. Rotation/frame = 2.0 \%. Crystal-detector distance = 25.0 mm. Measuring time = 450 s/\%. ; _diffrn_ambient_temperature 293(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 ; Nonius KappaCCD area-detector diffractometer ; _diffrn_measurement_method '\w scans' _diffrn_detector_area_resol_mean 0.055 _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 6608 _diffrn_reflns_av_R_equivalents 0.0355 _diffrn_reflns_av_sigmaI/netI 0.0426 _diffrn_reflns_limit_h_min -9 _diffrn_reflns_limit_h_max 8 _diffrn_reflns_limit_k_min -13 _diffrn_reflns_limit_k_max 13 _diffrn_reflns_limit_l_min -13 _diffrn_reflns_limit_l_max 13 _diffrn_reflns_theta_min 7.44 _diffrn_reflns_theta_max 27.44 _reflns_number_total 3673 _reflns_number_gt 2915 _reflns_threshold_expression >2\s(I) _computing_data_collection 'KappaCCD Reference Manual (Nonius, 1998)' _computing_cell_refinement 'DENZO-SMN (Otwinowski & Minor, 1997)' _computing_data_reduction 'DENZO-SMN (Otwinowski & Minor, 1997)' _computing_structure_solution 'SIR97 (Altomare, 1999)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _computing_molecular_graphics ; ORTEP-3 (Farrugia, 1997) and DIAMOND (Brandenburg, 1999) ; _computing_publication_material 'WinGX publication routines (Farrugia, 1999)' _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^ > 2\s(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^)+(0.0606P)^2^+0.3462P] 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 constr _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 3673 _refine_ls_number_parameters 212 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0645 _refine_ls_R_factor_gt 0.0472 _refine_ls_wR_factor_ref 0.1340 _refine_ls_wR_factor_gt 0.1200 _refine_ls_goodness_of_fit_ref 1.077 _refine_ls_restrained_S_all 1.077 _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 0.40094(6) 0.79655(4) 0.27440(4) 0.04817(17) Uani 1 1 d . . . N1 N 0.5166(3) 0.3767(2) 0.38211(19) 0.0473(5) Uani 1 1 d . . . H1 H 0.5021 0.3894 0.4628 0.071 Uiso 1 1 calc R . . O1 O 0.3110(3) 0.9298(2) 0.2421(2) 0.0671(5) Uani 1 1 d . . . O2 O 0.2610(2) 0.68333(18) 0.19789(16) 0.0511(4) Uani 1 1 d . . . O3 O 0.2338(2) 0.76289(17) 0.44638(16) 0.0477(4) Uani 1 1 d . . . O4 O 0.6045(3) 0.77180(19) 0.11630(16) 0.0540(4) Uani 1 1 d . . . O5 O 0.5818(2) 0.85442(18) 0.36296(17) 0.0528(4) Uani 1 1 d . . . O6 O 0.5250(3) 0.58800(18) 0.34671(16) 0.0528(4) Uani 1 1 d . . . C1 C 0.0290(4) 0.5637(3) 0.1627(3) 0.0605(7) Uani 1 1 d . . . H1A H 0.0294 0.6130 0.0861 0.091 Uiso 1 1 calc R . . H1B H -0.0956 0.5465 0.2057 0.091 Uiso 1 1 calc R . . H1C H 0.1016 0.4856 0.1400 0.091 Uiso 1 1 calc R . . C2 C 0.1098(3) 0.6357(2) 0.2509(2) 0.0464(5) Uani 1 1 d . . . C3 C 0.0209(4) 0.6438(3) 0.3814(3) 0.0515(6) Uani 1 1 d . . . H3 H -0.0904 0.6062 0.4102 0.062 Uiso 1 1 calc R . . C4 C 0.0869(3) 0.7042(2) 0.4717(2) 0.0453(5) Uani 1 1 d . . . C5 C -0.0189(4) 0.7047(3) 0.6107(3) 0.0597(7) Uani 1 1 d . . . H5A H 0.0643 0.6829 0.6639 0.090 Uiso 1 1 calc R . . H5B H -0.1110 0.6444 0.6246 0.090 Uiso 1 1 calc R . . H5C H -0.0777 0.7873 0.6326 0.090 Uiso 1 1 calc R . . C6 C 0.8629(5) 0.8195(3) -0.0495(3) 0.0659(8) Uani 1 1 d . . . H6A H 0.8486 0.7397 -0.0836 0.099 Uiso 1 1 calc R . . H6B H 0.9913 0.8279 -0.0557 0.099 Uiso 1 1 calc R . . H6C H 0.8171 0.8864 -0.0978 0.099 Uiso 1 1 calc R . . C7 C 0.7560(4) 0.8264(2) 0.0895(2) 0.0483(5) Uani 1 1 d . . . C8 C 0.8218(4) 0.8887(3) 0.1783(3) 0.0548(6) Uani 1 1 d . . . H8 H 0.9320 0.9273 0.1478 0.066 Uiso 1 1 calc R . . C9 C 0.7365(3) 0.8978(2) 0.3089(3) 0.0463(5) Uani 1 1 d . . . C10 C 0.8269(4) 0.9629(3) 0.3955(3) 0.0604(7) Uani 1 1 d . . . H10A H 0.7735 1.0478 0.4093 0.091 Uiso 1 1 calc R . . H10B H 0.9569 0.9641 0.3560 0.091 Uiso 1 1 calc R . . H10C H 0.8084 0.9184 0.4765 0.091 Uiso 1 1 calc R . . C11 C 0.5323(3) 0.4785(2) 0.3017(2) 0.0439(5) Uani 1 1 d . . . C12 C 0.5573(4) 0.4516(3) 0.1693(2) 0.0506(6) Uani 1 1 d . . . H12 H 0.5696 0.5175 0.1093 0.061 Uiso 1 1 calc R . . C13 C 0.5633(4) 0.3314(3) 0.1290(2) 0.0560(6) Uani 1 1 d . . . H13 H 0.5802 0.3162 0.0419 0.067 Uiso 1 1 calc R . . C14 C 0.5445(4) 0.2298(3) 0.2173(3) 0.0567(6) Uani 1 1 d . . . H14 H 0.5471 0.1474 0.1900 0.068 Uiso 1 1 calc R . . C15 C 0.5224(4) 0.2550(3) 0.3433(3) 0.0536(6) Uani 1 1 d . . . H15 H 0.5112 0.1894 0.4036 0.064 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 0.0498(3) 0.0595(3) 0.0367(2) -0.00715(17) -0.00906(16) -0.01698(19) N1 0.0526(11) 0.0566(12) 0.0350(9) -0.0068(9) -0.0144(8) -0.0042(9) O1 0.0737(13) 0.0634(13) 0.0666(12) 0.0049(10) -0.0208(10) -0.0111(10) O2 0.0514(9) 0.0659(11) 0.0382(8) -0.0061(8) -0.0118(7) -0.0148(8) O3 0.0489(9) 0.0550(10) 0.0399(8) -0.0095(7) -0.0097(7) -0.0093(8) O4 0.0601(10) 0.0653(12) 0.0372(8) -0.0039(8) -0.0077(7) -0.0220(9) O5 0.0554(10) 0.0605(11) 0.0447(9) -0.0105(8) -0.0115(7) -0.0179(8) O6 0.0647(11) 0.0543(10) 0.0415(9) -0.0113(8) -0.0144(8) -0.0095(8) C1 0.0696(17) 0.0625(17) 0.0568(15) -0.0095(13) -0.0241(13) -0.0191(14) C2 0.0524(13) 0.0450(13) 0.0453(12) -0.0032(10) -0.0171(10) -0.0086(10) C3 0.0534(13) 0.0515(14) 0.0496(13) -0.0056(11) -0.0088(11) -0.0155(11) C4 0.0484(12) 0.0438(12) 0.0422(12) -0.0029(9) -0.0084(9) -0.0036(10) C5 0.0645(16) 0.0641(17) 0.0469(14) -0.0019(12) -0.0039(12) -0.0166(13) C6 0.0705(18) 0.0720(19) 0.0476(14) -0.0001(13) 0.0021(13) -0.0171(15) C7 0.0532(13) 0.0443(13) 0.0444(12) 0.0001(10) -0.0046(10) -0.0107(10) C8 0.0542(14) 0.0513(15) 0.0584(15) -0.0027(12) -0.0085(11) -0.0196(12) C9 0.0490(12) 0.0374(12) 0.0554(14) -0.0067(10) -0.0167(10) -0.0072(10) C10 0.0610(15) 0.0513(15) 0.0758(18) -0.0174(13) -0.0265(14) -0.0095(12) C11 0.0422(11) 0.0554(14) 0.0364(11) -0.0102(10) -0.0114(9) -0.0081(10) C12 0.0629(15) 0.0546(15) 0.0356(11) -0.0066(10) -0.0136(10) -0.0055(12) C13 0.0701(16) 0.0616(16) 0.0388(12) -0.0119(11) -0.0173(11) -0.0037(13) C14 0.0696(16) 0.0511(15) 0.0531(14) -0.0130(12) -0.0217(12) -0.0008(12) C15 0.0655(15) 0.0523(15) 0.0458(13) -0.0016(11) -0.0193(11) -0.0043(12) _geom_special_details ; All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell s.u.'s are taken into account individually in the estimation of s.u.'s in distances, angles and torsion angles; correlations between s.u.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell s.u.'s is used for estimating s.u.'s 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 O1 1.588(2) . ? V1 O4 1.9828(18) . ? V1 O2 1.9830(17) . ? V1 O5 1.9886(17) . ? V1 O3 1.9891(17) . ? N1 C11 1.356(3) . ? N1 C15 1.367(3) . ? N1 H1 0.8600 . ? O2 C2 1.268(3) . ? O3 C4 1.273(3) . ? O4 C7 1.279(3) . ? O5 C9 1.272(3) . ? O6 C11 1.268(3) . ? C1 C2 1.507(3) . ? C1 H1A 0.9600 . ? C1 H1B 0.9600 . ? C1 H1C 0.9600 . ? C2 C3 1.393(4) . ? C3 C4 1.391(3) . ? C3 H3 0.9300 . ? C4 C5 1.502(3) . ? C5 H5A 0.9600 . ? C5 H5B 0.9600 . ? C5 H5C 0.9600 . ? C6 C7 1.505(4) . ? C6 H6A 0.9600 . ? C6 H6B 0.9600 . ? C6 H6C 0.9600 . ? C7 C8 1.388(4) . ? C8 C9 1.390(4) . ? C8 H8 0.9300 . ? C9 C10 1.497(3) . ? C10 H10A 0.9600 . ? C10 H10B 0.9600 . ? C10 H10C 0.9600 . ? C11 C12 1.423(3) . ? C12 C13 1.356(4) . ? C12 H12 0.9300 . ? C13 C14 1.405(4) . ? C13 H13 0.9300 . ? C14 C15 1.355(4) . ? C14 H14 0.9300 . ? C15 H15 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 O1 V1 O4 100.16(10) . . ? O1 V1 O2 100.14(10) . . ? O4 V1 O2 87.10(7) . . ? O1 V1 O5 99.18(10) . . ? O4 V1 O5 88.84(7) . . ? O2 V1 O5 160.66(8) . . ? O1 V1 O3 99.74(10) . . ? O4 V1 O3 160.09(8) . . ? O2 V1 O3 88.86(7) . . ? O5 V1 O3 88.56(7) . . ? C11 N1 C15 124.3(2) . . ? C11 N1 H1 117.8 . . ? C15 N1 H1 117.8 . . ? C2 O2 V1 128.23(15) . . ? C4 O3 V1 127.76(15) . . ? C7 O4 V1 125.76(16) . . ? C9 O5 V1 126.24(16) . . ? C2 C1 H1A 109.5 . . ? C2 C1 H1B 109.5 . . ? H1A C1 H1B 109.5 . . ? C2 C1 H1C 109.5 . . ? H1A C1 H1C 109.5 . . ? H1B C1 H1C 109.5 . . ? O2 C2 C3 124.7(2) . . ? O2 C2 C1 115.3(2) . . ? C3 C2 C1 120.0(2) . . ? C4 C3 C2 124.6(2) . . ? C4 C3 H3 117.7 . . ? C2 C3 H3 117.7 . . ? O3 C4 C3 125.0(2) . . ? O3 C4 C5 115.0(2) . . ? C3 C4 C5 120.0(2) . . ? C4 C5 H5A 109.5 . . ? C4 C5 H5B 109.5 . . ? H5A C5 H5B 109.5 . . ? C4 C5 H5C 109.5 . . ? H5A C5 H5C 109.5 . . ? H5B C5 H5C 109.5 . . ? C7 C6 H6A 109.5 . . ? C7 C6 H6B 109.5 . . ? H6A C6 H6B 109.5 . . ? C7 C6 H6C 109.5 . . ? H6A C6 H6C 109.5 . . ? H6B C6 H6C 109.5 . . ? O4 C7 C8 124.5(2) . . ? O4 C7 C6 114.8(2) . . ? C8 C7 C6 120.7(2) . . ? C7 C8 C9 125.3(2) . . ? C7 C8 H8 117.4 . . ? C9 C8 H8 117.4 . . ? O5 C9 C8 124.3(2) . . ? O5 C9 C10 115.9(2) . . ? C8 C9 C10 119.8(2) . . ? C9 C10 H10A 109.5 . . ? C9 C10 H10B 109.5 . . ? H10A C10 H10B 109.5 . . ? C9 C10 H10C 109.5 . . ? H10A C10 H10C 109.5 . . ? H10B C10 H10C 109.5 . . ? O6 C11 N1 119.8(2) . . ? O6 C11 C12 124.9(2) . . ? N1 C11 C12 115.3(2) . . ? C13 C12 C11 121.2(3) . . ? C13 C12 H12 119.4 . . ? C11 C12 H12 119.4 . . ? C12 C13 C14 120.8(2) . . ? C12 C13 H13 119.6 . . ? C14 C13 H13 119.6 . . ? C15 C14 C13 118.1(3) . . ? C15 C14 H14 120.9 . . ? C13 C14 H14 120.9 . . ? C14 C15 N1 120.2(3) . . ? C14 C15 H15 119.9 . . ? N1 C15 H15 119.9 . . ? 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 V1 O2 C2 -89.7(2) . . . . ? O4 V1 O2 C2 170.5(2) . . . . ? O5 V1 O2 C2 92.4(3) . . . . ? O3 V1 O2 C2 10.0(2) . . . . ? O1 V1 O3 C4 91.5(2) . . . . ? O4 V1 O3 C4 -86.8(3) . . . . ? O2 V1 O3 C4 -8.6(2) . . . . ? O5 V1 O3 C4 -169.4(2) . . . . ? O1 V1 O4 C7 76.2(2) . . . . ? O2 V1 O4 C7 176.0(2) . . . . ? O5 V1 O4 C7 -22.9(2) . . . . ? O3 V1 O4 C7 -105.5(3) . . . . ? O1 V1 O5 C9 -78.2(2) . . . . ? O4 V1 O5 C9 21.9(2) . . . . ? O2 V1 O5 C9 99.7(3) . . . . ? O3 V1 O5 C9 -177.8(2) . . . . ? V1 O2 C2 C3 -7.4(4) . . . . ? V1 O2 C2 C1 174.10(19) . . . . ? O2 C2 C3 C4 -0.7(5) . . . . ? C1 C2 C3 C4 177.7(3) . . . . ? V1 O3 C4 C3 4.5(4) . . . . ? V1 O3 C4 C5 -174.54(19) . . . . ? C2 C3 C4 O3 2.2(5) . . . . ? C2 C3 C4 C5 -178.8(3) . . . . ? V1 O4 C7 C8 15.9(4) . . . . ? V1 O4 C7 C6 -163.9(2) . . . . ? O4 C7 C8 C9 1.9(5) . . . . ? C6 C7 C8 C9 -178.3(3) . . . . ? V1 O5 C9 C8 -13.6(4) . . . . ? V1 O5 C9 C10 166.07(19) . . . . ? C7 C8 C9 O5 -3.1(5) . . . . ? C7 C8 C9 C10 177.2(3) . . . . ? C15 N1 C11 O6 179.9(2) . . . . ? C15 N1 C11 C12 -0.4(3) . . . . ? O6 C11 C12 C13 -179.9(3) . . . . ? N1 C11 C12 C13 0.4(4) . . . . ? C11 C12 C13 C14 0.2(4) . . . . ? C12 C13 C14 C15 -0.8(4) . . . . ? C13 C14 C15 N1 0.8(4) . . . . ? C11 N1 C15 C14 -0.2(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 N1 H1 O6 0.86 2.02 2.884(2) 177.4 2_666 _diffrn_measured_fraction_theta_max 0.972 _diffrn_reflns_theta_full 27.44 _diffrn_measured_fraction_theta_full 0.972 _refine_diff_density_max 0.308 _refine_diff_density_min -0.366 _refine_diff_density_rms 0.054 #===END data_3 _audit_creation_method SHELXL-97 _chemical_name_systematic ; pyridinium chlorido(pyridin-2-carboxylato-N,O)dioxidovandate(V) ; _chemical_name_common ; pyridinium chlorido(pyridin-2-carboxylato-N,O)dioxidovandate(V) ; _chemical_melting_point ? _chemical_formula_moiety 'C6 H4 Cl N O4 V, C5 H6 N' _chemical_formula_sum 'C11 H10 Cl N2 O4 V' _chemical_formula_weight 320.60 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' 'Cl' 'Cl' 0.1484 0.1585 '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' _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M P21/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 10.5709(3) _cell_length_b 9.9246(4) _cell_length_c 13.4691(4) _cell_angle_alpha 90.00 _cell_angle_beta 115.553(2) _cell_angle_gamma 90.00 _cell_volume 1274.85(7) _cell_formula_units_Z 4 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 3003 _cell_measurement_theta_min 0.920 _cell_measurement_theta_max 0.951 _exptl_crystal_description prism _exptl_crystal_colour green _exptl_crystal_size_max 0.20 _exptl_crystal_size_mid 0.07 _exptl_crystal_size_min 0.05 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.670 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 648 _exptl_absorpt_coefficient_mu 0.998 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.8254 _exptl_absorpt_correction_T_max 0.9518 _exptl_absorpt_process_details 'SCALEPACK (Otwinowski & Minor, 1997)' _exptl_special_details ; 205 frames in 6 sets of \w scans. Rotation/frame = 2.0 \%. Crystal-detector distance = 25.00 mm. Measuring time = 120 s/\%. ; _diffrn_ambient_temperature 293(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 ; Nonius KappaCCD area-detector diffractometer ; _diffrn_measurement_method '\w scans' _diffrn_detector_area_resol_mean 0.055 _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 5461 _diffrn_reflns_av_R_equivalents 0.0217 _diffrn_reflns_av_sigmaI/netI 0.0314 _diffrn_reflns_limit_h_min -13 _diffrn_reflns_limit_h_max 13 _diffrn_reflns_limit_k_min -12 _diffrn_reflns_limit_k_max 12 _diffrn_reflns_limit_l_min -17 _diffrn_reflns_limit_l_max 17 _diffrn_reflns_theta_min 3.10 _diffrn_reflns_theta_max 27.46 _reflns_number_total 2893 _reflns_number_gt 2230 _reflns_threshold_expression >2\s(I) _computing_data_collection 'KappaCCD Reference Manual (Nonius, 1998)' _computing_cell_refinement 'DENZO-SMN (Otwinowski & Minor, 1997)' _computing_data_reduction 'DENZO-SMN (Otwinowski & Minor, 1997)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 2008)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _computing_molecular_graphics ; ORTEP-3 (Farrugia, 1997) and DIAMOND (Brandenburg, 1999) ; _computing_publication_material 'WinGX publication routines (Farrugia, 1999)' _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^ > 2\s(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^)+(0.0533P)^2^+0.3673P] 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 constr _refine_ls_extinction_method SHELXL _refine_ls_extinction_coef 0.014(2) _refine_ls_extinction_expression 'Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^' _refine_ls_number_reflns 2893 _refine_ls_number_parameters 174 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0552 _refine_ls_R_factor_gt 0.0375 _refine_ls_wR_factor_ref 0.1047 _refine_ls_wR_factor_gt 0.0937 _refine_ls_goodness_of_fit_ref 1.042 _refine_ls_restrained_S_all 1.042 _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 0.19229(4) 0.38300(4) 0.32450(3) 0.04383(15) Uani 1 1 d . . . Cl1 Cl 0.28719(7) 0.22835(7) 0.24505(5) 0.0588(2) Uani 1 1 d . . . N1 N 0.18251(19) 0.5214(2) 0.44138(16) 0.0451(4) Uani 1 1 d . . . N2 N 0.5744(2) 0.1515(3) 0.47476(19) 0.0582(6) Uani 1 1 d . . . H2 H 0.5019 0.2031 0.4494 0.087 Uiso 1 1 calc R . . O3 O 0.37297(16) 0.35259(18) 0.46281(12) 0.0481(4) Uani 1 1 d . . . O4 O 0.50721(19) 0.4061(2) 0.63849(14) 0.0620(5) Uani 1 1 d . . . O2 O 0.14297(19) 0.4991(2) 0.22991(14) 0.0612(5) Uani 1 1 d . . . O1 O 0.05527(18) 0.3015(2) 0.31429(16) 0.0602(5) Uani 1 1 d . . . C1 C 0.4018(2) 0.4203(3) 0.55264(19) 0.0462(5) Uani 1 1 d . . . C2 C 0.2911(2) 0.5212(2) 0.54150(19) 0.0443(5) Uani 1 1 d . . . C3 C 0.2980(3) 0.6078(3) 0.6240(2) 0.0559(6) Uani 1 1 d . . . H3 H 0.3752 0.6074 0.6923 0.067 Uiso 1 1 calc R . . C4 C 0.1864(3) 0.6958(3) 0.6020(2) 0.0614(7) Uani 1 1 d . . . H4 H 0.1871 0.7547 0.6560 0.074 Uiso 1 1 calc R . . C5 C 0.0753(3) 0.6943(3) 0.4994(3) 0.0620(7) Uani 1 1 d . . . H5 H -0.0002 0.7522 0.4832 0.074 Uiso 1 1 calc R . . C6 C 0.0765(3) 0.6070(3) 0.4213(2) 0.0564(6) Uani 1 1 d . . . H6 H 0.0012 0.6071 0.3519 0.068 Uiso 1 1 calc R . . C7 C 0.5925(3) 0.0657(3) 0.4075(2) 0.0678(8) Uani 1 1 d . . . H7 H 0.5295 0.0638 0.3335 0.081 Uiso 1 1 calc R . . C8 C 0.7040(4) -0.0202(3) 0.4466(3) 0.0767(9) Uani 1 1 d . . . H8 H 0.7168 -0.0826 0.4001 0.092 Uiso 1 1 calc R . . C9 C 0.7987(3) -0.0130(3) 0.5574(3) 0.0690(8) Uani 1 1 d . . . H9 H 0.8756 -0.0704 0.5863 0.083 Uiso 1 1 calc R . . C10 C 0.7760(3) 0.0801(3) 0.6224(2) 0.0633(7) Uani 1 1 d . . . H10 H 0.8384 0.0876 0.6963 0.076 Uiso 1 1 calc R . . C11 C 0.6629(3) 0.1612(3) 0.5794(2) 0.0572(6) Uani 1 1 d . . . H11 H 0.6473 0.2244 0.6238 0.069 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 0.0413(2) 0.0441(3) 0.0441(2) 0.00297(16) 0.01663(16) 0.00355(16) Cl1 0.0653(4) 0.0600(4) 0.0501(3) -0.0031(3) 0.0239(3) 0.0117(3) N1 0.0445(9) 0.0399(11) 0.0514(10) 0.0053(8) 0.0212(8) 0.0032(8) N2 0.0453(11) 0.0589(15) 0.0671(14) 0.0160(11) 0.0212(10) 0.0039(9) O3 0.0463(8) 0.0520(10) 0.0437(8) -0.0002(7) 0.0172(7) 0.0096(7) O4 0.0515(9) 0.0765(14) 0.0486(9) -0.0027(9) 0.0127(8) 0.0072(9) O2 0.0680(11) 0.0588(12) 0.0571(10) 0.0128(9) 0.0274(9) 0.0138(9) O1 0.0514(9) 0.0607(12) 0.0690(11) -0.0090(9) 0.0264(8) -0.0086(8) C1 0.0474(11) 0.0479(14) 0.0454(12) 0.0045(10) 0.0220(10) 0.0009(10) C2 0.0496(11) 0.0410(12) 0.0484(12) 0.0053(10) 0.0269(10) 0.0002(9) C3 0.0725(16) 0.0528(16) 0.0490(13) 0.0017(11) 0.0325(12) 0.0029(12) C4 0.0898(19) 0.0460(16) 0.0698(17) 0.0034(12) 0.0548(16) 0.0077(13) C5 0.0678(16) 0.0515(16) 0.0780(18) 0.0097(14) 0.0420(15) 0.0158(13) C6 0.0540(13) 0.0495(15) 0.0649(15) 0.0063(12) 0.0249(12) 0.0103(11) C7 0.0748(17) 0.0663(19) 0.0488(14) 0.0017(14) 0.0139(13) -0.0158(15) C8 0.111(3) 0.0551(18) 0.084(2) -0.0182(16) 0.062(2) -0.0121(18) C9 0.0629(16) 0.0580(18) 0.092(2) 0.0200(16) 0.0384(15) 0.0187(13) C10 0.0574(14) 0.076(2) 0.0463(13) 0.0051(13) 0.0132(11) 0.0021(13) C11 0.0647(15) 0.0553(16) 0.0596(15) 0.0015(12) 0.0342(13) 0.0028(12) _geom_special_details ; All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell s.u.'s are taken into account individually in the estimation of s.u.'s in distances, angles and torsion angles; correlations between s.u.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell s.u.'s is used for estimating s.u.'s 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 O1 1.6124(18) . ? V1 O2 1.6276(18) . ? V1 O3 2.0347(15) . ? V1 N1 2.125(2) . ? V1 Cl1 2.3308(8) . ? N1 C6 1.337(3) . ? N1 C2 1.342(3) . ? N2 C7 1.316(4) . ? N2 C11 1.316(3) . ? N2 H2 0.8600 . ? O3 C1 1.300(3) . ? O4 C1 1.219(3) . ? C1 C2 1.498(3) . ? C2 C3 1.381(4) . ? C3 C4 1.394(4) . ? C3 H3 0.9300 . ? C4 C5 1.374(4) . ? C4 H4 0.9300 . ? C5 C6 1.368(4) . ? C5 H5 0.9300 . ? C6 H6 0.9300 . ? C7 C8 1.363(5) . ? C7 H7 0.9300 . ? C8 C9 1.395(5) . ? C8 H8 0.9300 . ? C9 C10 1.364(5) . ? C9 H9 0.9300 . ? C10 C11 1.347(4) . ? C10 H10 0.9300 . ? C11 H11 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 O1 V1 O2 108.41(10) . . ? O1 V1 O3 117.23(9) . . ? O2 V1 O3 132.76(9) . . ? O1 V1 N1 93.36(9) . . ? O2 V1 N1 91.19(9) . . ? O3 V1 N1 75.17(7) . . ? O1 V1 Cl1 100.32(7) . . ? O2 V1 Cl1 99.37(7) . . ? O3 V1 Cl1 84.42(5) . . ? N1 V1 Cl1 159.03(6) . . ? C6 N1 C2 118.9(2) . . ? C6 N1 V1 124.38(17) . . ? C2 N1 V1 116.72(15) . . ? C7 N2 C11 122.5(2) . . ? C7 N2 H2 118.8 . . ? C11 N2 H2 118.8 . . ? C1 O3 V1 121.75(14) . . ? O4 C1 O3 125.1(2) . . ? O4 C1 C2 121.8(2) . . ? O3 C1 C2 113.12(19) . . ? N1 C2 C3 122.2(2) . . ? N1 C2 C1 113.2(2) . . ? C3 C2 C1 124.5(2) . . ? C2 C3 C4 118.2(2) . . ? C2 C3 H3 120.9 . . ? C4 C3 H3 120.9 . . ? C5 C4 C3 119.0(3) . . ? C5 C4 H4 120.5 . . ? C3 C4 H4 120.5 . . ? C6 C5 C4 119.6(3) . . ? C6 C5 H5 120.2 . . ? C4 C5 H5 120.2 . . ? N1 C6 C5 122.1(3) . . ? N1 C6 H6 118.9 . . ? C5 C6 H6 118.9 . . ? N2 C7 C8 119.8(3) . . ? N2 C7 H7 120.1 . . ? C8 C7 H7 120.1 . . ? C7 C8 C9 118.9(3) . . ? C7 C8 H8 120.6 . . ? C9 C8 H8 120.6 . . ? C10 C9 C8 118.6(3) . . ? C10 C9 H9 120.7 . . ? C8 C9 H9 120.7 . . ? C11 C10 C9 119.9(3) . . ? C11 C10 H10 120.1 . . ? C9 C10 H10 120.1 . . ? N2 C11 C10 120.4(3) . . ? N2 C11 H11 119.8 . . ? C10 C11 H11 119.8 . . ? 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 V1 N1 C6 -62.9(2) . . . . ? O2 V1 N1 C6 45.6(2) . . . . ? O3 V1 N1 C6 179.8(2) . . . . ? Cl1 V1 N1 C6 166.20(16) . . . . ? O1 V1 N1 C2 117.07(17) . . . . ? O2 V1 N1 C2 -134.41(17) . . . . ? O3 V1 N1 C2 -0.23(16) . . . . ? Cl1 V1 N1 C2 -13.8(3) . . . . ? O1 V1 O3 C1 -85.4(2) . . . . ? O2 V1 O3 C1 78.2(2) . . . . ? N1 V1 O3 C1 0.67(17) . . . . ? Cl1 V1 O3 C1 175.83(18) . . . . ? V1 O3 C1 O4 179.2(2) . . . . ? V1 O3 C1 C2 -0.9(3) . . . . ? C6 N1 C2 C3 -1.0(3) . . . . ? V1 N1 C2 C3 178.97(19) . . . . ? C6 N1 C2 C1 179.8(2) . . . . ? V1 N1 C2 C1 -0.1(2) . . . . ? O4 C1 C2 N1 -179.5(2) . . . . ? O3 C1 C2 N1 0.7(3) . . . . ? O4 C1 C2 C3 1.5(4) . . . . ? O3 C1 C2 C3 -178.4(2) . . . . ? N1 C2 C3 C4 1.4(4) . . . . ? C1 C2 C3 C4 -179.6(2) . . . . ? C2 C3 C4 C5 -0.8(4) . . . . ? C3 C4 C5 C6 -0.1(4) . . . . ? C2 N1 C6 C5 0.1(4) . . . . ? V1 N1 C6 C5 -179.9(2) . . . . ? C4 C5 C6 N1 0.5(4) . . . . ? C11 N2 C7 C8 2.2(4) . . . . ? N2 C7 C8 C9 -1.5(5) . . . . ? C7 C8 C9 C10 -0.1(5) . . . . ? C8 C9 C10 C11 0.9(5) . . . . ? C7 N2 C11 C10 -1.3(4) . . . . ? C9 C10 C11 N2 -0.3(5) . . . . ? 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 N2 H2 O3 0.86 2.07 2.872(3) 153.8 . N2 H2 Cl1 0.86 2.72 3.357(2) 131.9 . _diffrn_measured_fraction_theta_max 0.992 _diffrn_reflns_theta_full 27.46 _diffrn_measured_fraction_theta_full 0.992 _refine_diff_density_max 0.230 _refine_diff_density_min -0.319 _refine_diff_density_rms 0.055