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Issue 5, 2011
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Crystal structures of fluorinated aryl biscarbonates and a biscarbamate: a counterpoise between weak intermolecular interactions and molecular symmetry

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Abstract

Conformational features and supramolecular structural organization in three aryl biscarbonates and an aryl biscarbamate with rigid acetylenic unit providing variable spacer lengths have been probed to gain insights into the packing features associated with molecular symmetry and the intermolecular interactions involving ‘organic’ fluorine. Four structures but-2-yne-1,4-diyl bis(2,3,4,5,6-pentafluorophenylcarbonate), 1; but-2-yne-1,4-diyl bis(4-fluorophenylcarbonate), 2; but-2-yne-1,4-diyl bis(2,3,4,5,6-pentafluorophenylcarbamate), 3 and hexa-2,4-diyne-1,6-diyl bis(2,3,4,5,6-pentafluorophenylcarbonate), 4 have been analyzed in this context. Compound 1 adopts a non-centrosymmetric “twisted” (syn) conformation, whereas 2, 3 and 4 acquire a centrosymmetric “extended” (anti) conformation. Weak intermolecular interactions and in particular those involving fluorine are found to dictate this conformational variation in the crystal structure of 1. A single-crystal neutron diffraction study at 90 K was performed on 1 to obtain further insights into these interactions involving ‘organic’ fluorine.

Graphical abstract: Crystal structures of fluorinated aryl biscarbonates and a biscarbamate: a counterpoise between weak intermolecular interactions and molecular symmetry

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Publication details

The article was received on 14 Aug 2010, accepted on 12 Oct 2010 and first published on 22 Nov 2010


Article type: Paper
DOI: 10.1039/C0CE00537A
Citation: CrystEngComm, 2011,13, 1531-1538
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    Crystal structures of fluorinated aryl biscarbonates and a biscarbamate: a counterpoise between weak intermolecular interactions and molecular symmetry

    A. G. Dikundwar, Ch. Venkateswarlu, R. O. Piltz, S. Chandrasekaran and T. N. Guru Row, CrystEngComm, 2011, 13, 1531
    DOI: 10.1039/C0CE00537A

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