C18H17ClN2O2, monoclinic, P121/c1 (no. 14), a = 12.2900(9) Å, b = 13.325(1) Å, c = 10.482(1) Å, b = 102.69(1)°, V = 1674.7 Å 3 , Z = 4, R gt (F) = 0.053, wRref(F 2 ) = 0.162, T = 293 K.
Source of materialThe title compound was obtained by 1,3-dipolar cycloaddition of 5-chloromethyl-2-methyl-3-phenyl-2,5-dihydroisoxazole and benzhydroximoyl chloride in the presence of triethylamine as a base [1][2][3][4][5][6]. Purification by chromatography (ethyl acetate/petrol ether) and crystallization from diethyl ether gave the title cycloadduct in the form of colorless crystals [1,2] (m.p. 381-382 K).
DiscussionThe N2=C4 double bond of the isoxazole moiety is clearly characterized by the distance of 1.288(4) Å. The dihedral angle of the bicyclic system is 75.0(1)°. The tetrahydroisoxazole moiety of the bicyclic system shows an envelope conformation, where O1 is out of plane ( figure, top). The cell plot shows a layer-type packing of the molecules. In the a,c view of the cell we identify polar layers generated by the heteroatoms of the isoxazole rings and the chlorine atoms in the b,c plane stacked along the a axis. In the same direction we find non-polar layers built up by the phenyl moieties (figure, bottom).
C 11H12BrNO, orthorhombic, Pccn (no. 56), a = 13.1274(7) Å, b = 23.309(1) Å, c = 6.995(1) Å, V = 2140.4 Å 3 , Z = 8, R gt(F) = 0.065, wRref(F 2 ) = 0.207, T = 293 K.
Source of materialThe title compound has been obtained by bromocyclization of 3-phenyl-4-pentenal oxime [1][2][3][4][5][6][7]. The two diastereoisomers (ratio 40:60) were separated by column chromatography (ethyl acetate/methanol), whereby crystallization of the major isomer from dichloromethane furnished the title nitrone in the form of colorless crystals (m.p. 398-401 K).
DiscussionThe pyrroline ring system has an envelope conformation, where C2 is situated out-of-plane. Both ring systems of the molecule have a nearly perfect perpendicular orientation of 88.9 (2)
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