A. P. Marjani, J. Khalafy, N. Pesyan
Aug 1, 2013
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Journal
South African journal of chemistry
Abstract
The titlecompoundethyl 2-(benzo[d]oxazol-2-yl)-5-oxo-3-( o -tolylamino)-2,5-dihydroisoxazole-4-carboxylate (5) was synthesized and studied by the single crystal X-ray diffraction method. Its structure was confirmed by IR, 1 H and 13 C NMR spectroscopy, microanalyses, and X-ray single crystal structure determination. Compound 5 crystallized in the monoclinic system, space group P2 1 / c , a=11.9936(3) A, b =13.9638(3) A, c=11.5126(4) A, α =γ=90 °,β =108.939(3) °, V=1823.70(9)A 3 ,Z=4, R1=0.050 and wR2 = 0.130. Compound 5 shows an intramolecular hydrogen bond between N9–H...O3 atoms. The H-bond and donor–acceptor (N9...O3) distances were obtained 2.165 and 2.798 A, respectively. The crystal structure of 5 also shows a weak interaction between O1 and O26 atoms with distance of 2.985 A. The benzo[d]oxazole and o-toluidine rings moieties are not collimated together on isoxazolone ring. The torsion angles of N9–C8–N7–C17, O6–N7–C17–O18 equal –49.63 ° and 68.67 °, respectively. KEYWORDS Isoxazolone; 2-chlorobenzoxazole; N-substituted isoxazolone; single crystal X-ray structure; hydrogen bond.