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Synthesis and Crystal Structure of Ethyl 2-(benzo[d]oxazol-2-yl)-5-oxo-3-(o-tolylamino)- 2,5-dihydroisoxazole-4-carboxylate
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, 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)Å3,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.
