Crystal structure of rel-(2R,3S)-2-bromomethyl-3-phenyl-3,4-dihydro- 2H-pyrrole 1-oxide, C11H12BrNO

Abstract

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)