Crystal structure of rel-(2R,3aS)-2-bromomethyl-3,3a,4,5,6,7-hexahydro- 2H-indole 1-oxide, C9H14BrNO

Abstract

Source of materialThe title compound has been obtained by bromocyclization of 2-allylcyclohexanone oxime [1][2][3][4]. The two diastereoisomers (ratio 67:33) were separated by column chromatography using ethyl acetate/methanol (7:3), whereby crystallization of the minor isomer from dichloromethane furnished the title nitrone in the form of brownish crystals (m.p. 375-376 K). DiscussionThe six-membered ring system shows a chair conformation and the pyrrolidine ring has an envelope conformation, where C2 is out of plane. The double bond N1=C8 is clearly characterized by the distance of 1.298(7) Å. The NO distance of the neighboring N-oxide function is 1.309 (6) Å. In the packing diagram of the cell plot we observe an antiparallel orientation of the molecules along the c axis and a face-to-face stacking of the molecules along the a axis.Z. Kristallogr. NCS 221 (2006) 89-90