The effect of fluorinated aryl substituents on the crystal structures of 1,2,3,5-dithiadiazolyl radicals

Caroline S Clarke, Delia A Haynes, J Nicholas B Smith, Andrei S Batsanov, Judith A K Howard, Sofia I Pascu, Jeremy M Rawson

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Abstract

The crystal structures of six new partially fluorinated aryl 1,2,3,5-dithiadiazolyls [ArCNSSN]˙ are reported [Ar = 2,6-F2C6H3 (4); Ar = 3,4-F2C6H3 (5); Ar = 3,5-F2C6H3 (6); Ar = 2,3,6-F3C6H2 (9); Ar = 2,4,6-F3C6H2 (11); and Ar = 3,4,5-F3C6H2 (12)] and compared with three previously reported structures in this series (Ar = 2,3-F2C6H3 (1); Ar = 2,5-F2C6H3 (3); Ar = 2,3,4-F3C6H2 (7)]. Radical 4 is shown to be polymorphic. Molecular electrostatic potential maps have been used to rationalise these structures. These reveal that whilst single F atoms appear to have little structure-directing influence, combinations of an ortho-F on the phenyl ring and a heterocyclic ring N, or several F atoms located in mutually ortho positions with respect to each other, generate significant regions of negative charge which have a substantial structure-directing influence.
Original languageEnglish
Pages (from-to)172-185
Number of pages14
JournalCrystEngComm
Volume12
Issue number1
DOIs
Publication statusPublished - 2010

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    Clarke, C. S., Haynes, D. A., Smith, J. N. B., Batsanov, A. S., Howard, J. A. K., Pascu, S. I., & Rawson, J. M. (2010). The effect of fluorinated aryl substituents on the crystal structures of 1,2,3,5-dithiadiazolyl radicals. CrystEngComm, 12(1), 172-185. https://doi.org/10.1039/b911636b