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

Sladjana B. NovakovićVinca Institute of Nuclear Sciences, Laboratory of Theoretical Physics and Condensed Matter Physics, PO Box 522, 11001 Belgrade, Republic of Serbia. [email protected]Maja Vitorović-TodorovićMilitary-Technical Institute, Ratka Resanovića 1, 11000 Belgrade, Republic of SerbiaGoran A. Bogdanović'Vinča' Institute of Nuclear Sciences, Laboratory of Theoretical Physics and Condensed Matter Physics, PO Box 522, 11001 Belgrade, Republic of SerbiaBranko J. DrakulićDepartment of Chemistry–IChTM, University of Belgrade, Njegoševa 12, 11000 Belgrade, Republic of Serbia
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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.

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