Crystal structure of 1-(6-(1-(perfluorophenylimino)ethyl)pyridin-2-yl)ethanone, C15H9F5N2O

Abstract

C 15H 9 F 5 N 2 O,monoclinic, P 121 / c 1(no. 14), a =10.486(2) Å, b =10.510(2) Å, c =12.912(2) Å, Source of materialAsolution of 2,6-diacetylpyridine (0.41 g, 2.5 mmol),2,3,4,5,6-pentafluoroaniline (0.46 g, 2.5 mmol), Silica-Aluminacatalyst support(0.2 g) and 4Åmolecularsieve (1.0 g) in toluene (12 mL) wasstirred at30-40°Cfor 24 hours. Then the reaction mixture wasf iltered, and the moleculars ieve wasw ashed with toluene severaltimes. The toluene of combined filtrates wasremoved in vacuo. Anhydrous methanol(10 mL)wasadded to the residue. A yellow solid wasfiltered off to obtain the title compound in 68.8 % yield. Single crystals suitable for X-raymeasurements were obtained by crystallization from benzene. DiscussionRecently, aserieso fi minopyridyl-based ferrous and cobaltous complexes have obtained greatinterest due to their high activities for ethylene oligomerization and polymerization [1][2][3][4]. The catalytic performances have been greatly improved by introducing halogen atoms into ligands [5,6], and anew method for synthesis of halogen substituted bis(imino)pyridines hasbeen reported [7]. The title compound is in the E conformation. The N2-C7bond distancei s1 .270(3) Å,w hich is noticeably shorter thant he N2-C10 bond length of 1.404(3) Å,soitindicates thatatypical C = Ndouble bond hasf ormed between N2and C7atoms. The bond lengths of N1-C2(1.342(3) Å)and N1-C6(1.332(3) Å) are between the values for single bond and double bond. The dihedralangle betweenthe best planes of N1-C2-C3-C4-C5-C6 and C10-C11-C12-C13-C14-C15 is 63.32(6)°. The torsion angles of