Abstract

MARJANI, A. Poursattar; KHALAFY, J.  and  PESYAN, N. Noroozi. Synthesis and crystal structure of ethyl 2-(benzo[d]oxazol-2-yl)-5-oxo-3-(o-tolylamino)-2,5-dihydroisoxazole-4-carboxylate. S.Afr.j.chem. (Online) [online]. 2013, vol.66, pp.00-00. ISSN 1996-840X.

The title compound ethyl 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, ¹H and ¹³C NMR spectroscopy, microanalyses, and X-ray single crystal structure determination. Compound 5 crystallized in the monoclinic system, space group P2₁/c, a = 11.9936(3) Å, b = 13.9638(3) Å, c = 11.5126(4) Å, α = γ = 90°, β = 108.939(3) °, V = 1823.70(9) ų,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 Å, respectively. The crystal structure of 5 also shows a weak interaction between O1 and O26 atoms with distance of 2.985 Å. 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.

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