Weak intermolecular interactions in 11-chloro-2,3,4,5-tetrahydro-1H-cyclohepta[b]quinoline

Acta Crystallogr C. 2008 Sep;64(Pt 9):o502-4. doi: 10.1107/S0108270108022221. Epub 2008 Aug 13.

Abstract

The title compound, C(14)H(14)ClN, is a chloro analogue of tacrine, an acetylcholinesterase inhibitor. The compound comprises a seven-membered alicyclic ring whose CH donor groups are engaged in extensive intermolecular interactions. The important feature of this crystal structure is that, regardless of the presence of two typical hydrogen-bonding acceptors, viz. chlorine and nitrogen, the corresponding C-H...Cl and C-H...N interactions take no significant role in crystal stabilization. The molecules form dimers through pi-pi interactions with an interplanar distance between interacting pyridine rings of 3.576 (1) A. Within the dimers, the molecules are additionally interconnected by four C-H...pi interactions. The dimers arrange into regular columns via further intermolecular C-H...pi interactions.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Cholinesterase Inhibitors / chemistry*
  • Crystallography, X-Ray
  • Dimerization
  • Hydrogen Bonding
  • Quinolines / chemistry*
  • Tacrine / chemistry

Substances

  • 11-chloro-2,3,4,5-tetrahydro-1H-cyclohepta(b)quinoline
  • Cholinesterase Inhibitors
  • Quinolines
  • Tacrine