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

Dikundwar, Amol G and Venkateswarlu, Ch and Piltz, Ross O and Chandrasekaran, Srinivasan and Row, Tayur Guru N (2011) Crystal structures of fluorinated aryl biscarbonates and a biscarbamate: a counterpoise between weak intermolecular interactions and molecular symmetry. In: CrystEngComm, 13 (5). pp. 1531-1538.

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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.

Item Type: Journal Article
Additional Information: Copyright of this article belongs to Royal Society of Chemistry.
Department/Centre: Division of Chemical Sciences > Organic Chemistry
Division of Chemical Sciences > Solid State & Structural Chemistry Unit
Date Deposited: 24 Mar 2011 06:04
Last Modified: 24 Mar 2011 06:04
URI: http://eprints.iisc.ernet.in/id/eprint/36212

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