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