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Issue 7, 2010
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C–H⋯F–C hydrogen bonding in 1,2,3,5-tetrafluorobenzene and other fluoroaromatic compounds and the crystal structure of alloxan revisited

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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 FF 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⋯π interaction, which appears improbable for the molecule. The role of weak intermolecular interactions in the crystal packing of predominantly non-polar compounds is highlighted.

Graphical abstract: C–H⋯F–C hydrogen bonding in 1,2,3,5-tetrafluorobenzene and other fluoroaromatic compounds and the crystal structure of alloxan revisited

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Publication details

The article was received on 30 Nov 2009, accepted on 02 Feb 2010 and first published on 17 Mar 2010


Article type: Paper
DOI: 10.1039/B925082D
Citation: CrystEngComm, 2010,12, 2079-2085
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    C–H⋯F–C hydrogen bonding in 1,2,3,5-tetrafluorobenzene and other fluoroaromatic compounds and the crystal structure of alloxan revisited

    T. S. Thakur, M. T. Kirchner, D. Bläser, R. Boese and G. R. Desiraju, CrystEngComm, 2010, 12, 2079
    DOI: 10.1039/B925082D

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