C-H···F-C hydrogen bonding in 1,2,3,5-tetrafluorobenzene and other fluoroaromatic compounds and the crystal structure of alloxan revisited

Thakur, Tejender S. ; Kirchner, Michael T. ; Blaser, Dieter ; Boese, Roland ; Desiraju, Gautam R. (2010) C-H···F-C hydrogen bonding in 1,2,3,5-tetrafluorobenzene and other fluoroaromatic compounds and the crystal structure of alloxan revisited CrystEngComm, 12 (7). pp. 2079-2085. ISSN 1466-8033

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Official URL: http://pubs.rsc.org/en/Content/ArticleLanding/2010...

Related URL: http://dx.doi.org/10.1039/B925082D

Abstract

The crystal structure of 1,2,3,5-tetrafluorobenzene, 1, has been determined and is compared with those of other polyfluoro-substituted benzenes. Compound 1 has a layered monoclinic structure in which the layers are held by bifurcated C-H···F-C interactions. Short F···F separations are also observed. The layers are stacked at van der Waals separation to give a 4 Å packing. This structure is adopted instead of an alternative tetragonal structure adopted by fluorobenzene and a number of related compounds such as benzonitrile, pyridine N-oxide and alloxan. Compound 1 does not take the tetragonal structure mostly because this structure would demand the formation of a C-F···∏ interaction, which appears improbable for the molecule. The role of weak intermolecular interactions in the crystal packing of predominantly non-polar compounds is highlighted.

Item Type:Article
Source:Copyright of this article belongs to Royal Society of Chemistry.
ID Code:11410
Deposited On:09 Nov 2010 06:14
Last Modified:29 May 2011 15:42

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