oa South African Journal of Chemistry - Synthesis and crystal structure of ethyl 2-(benzo[d]oxazol-2-yl)-5-oxo-3-(o-tolylamino)-2,5-dihydroisoxazole-4-carboxylate : research article
|Article Title||Synthesis and crystal structure of ethyl 2-(benzo[d]oxazol-2-yl)-5-oxo-3-(o-tolylamino)-2,5-dihydroisoxazole-4-carboxylate : research article|
|© Publisher:||South African Chemical Institute (SACI)|
|Journal||South African Journal of Chemistry|
|Affiliations||1 Urmia University, Iran, 2 Urmia University, Iran and 3 Urmia University, Iran|
|Publication Date||Jan 2013|
|Pages||27 - 31|
|Keyword(s)||2-chlorobenzoxazole, Hydrogen bond, Isoxazolone, N-substituted isoxazolone and Single crystal X-ray structure|
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) 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.
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