Received 29 November 2011
aThe School of Chemistry, The University of Manchester, Manchester M13 9PL, England,bDepartment of Chemistry, Faculty of Science, University of Urmia, Urmia 57153-165, Iran, and cDepartment of Chemical Engineering, University of Urmia, Urmia 57153-165, Iran
Correspondence e-mail: firstname.lastname@example.org
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.
For background information on the chemistry of related compounds, see: Baradarani et al. (2006); Rashidi et al. (2009, 2011). For related structures, see: Helliwell et al. (2010, 2012). For graph-set notation, see: Etter et al. (1990).
Data collection: SMART (Bruker, 2001); cell refinement: SAINT (Bruker, 2002); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: XP in SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXTL.
Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: PK2373 ).
The authors are grateful to the University of Urmia for financial support of this work.
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