Acta Crystallographica Section E

Structure Reports Online

Volume 68, Part 1 (January 2012)

organic compounds

Acta Cryst. (2012). E68, o234    [ doi:10.1107/S1600536811053918 ]


M. Helliwell, M. M. Baradarani, M. Alyari, A. Afghan and J. A. Joule

Abstract: Reaction of 2-(4-chloro-3,3,7-trimethyl-2,3-dihydro-1H-indol-2-yl­idene)propane­dial with hydroxyl­amine gives the title compound, C14H14ClN3O, in which the ring N atom is essentially planar [sum of angles around the ring N atom = 361°], indicating conjugation with the 2-cyano­acryl­amide unit. The orientation of the acetamide group arises from intra­molecular hydrogen bonding between the indole N-H and carbonyl groups. In the crystal, inversion-related acetamide groups form N-H...O hydrogen-bonded dimers in graph-set R22(8) motifs, whilst dimers are also formed by pairs of amine-nitrile N-H...N hydrogen bonds in R22(12) motifs. These inter­actions together generate ribbons that propagate along the b-axis direction.

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