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

2-(4-Chloro-3,3,7-trimethyl-2,3-dihydro-1H-indol-2-ylidene)-2-cyanoacetamide

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-HO hydrogen-bonded dimers in graph-set R₂²(8) motifs, whilst dimers are also formed by pairs of amine-nitrile N-HN hydrogen bonds in R₂²(12) motifs. These interactions together generate ribbons that propagate along the b-axis direction.

Online 23 December 2011

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