Hirshfeld surface analysis of substituted phenols

Adam D. Martin, Karel J. Hartlieb, Alexandre N. Sobolev, Colin L. Raston

Research output: Contribution to journalArticlepeer-review

65 Citations (Scopus)


The effect of para-substituents on the crystal packing of phenols has been investigated, for systems bearing nonpolar groups (tert-butyl and benzyl, compounds 1 and 2, respectively) and for methylene linked bis-phenol bearing polar nitro groups (compound 3). Remarkable for 1 and 2, the asymmetric unit has six molecules, which form infinite helical hydrogen bonded arrays in the extended structures, whereas compound 3 bearing nitro groups coplanar with the phenol rings forms almost columnar arrays. Hirshfeld surface analysis is used to show that despite packing in a nearly identical manner, 1 and 2 are distinctly different in their interactions, and these structures are compared to compound 3, where the solid-state interactions are dominated by the nitro moieties.
Original languageEnglish
Pages (from-to)5302-5306
Number of pages5
JournalCrystal Growth and Design
Issue number12
Publication statusPublished - 2010
Externally publishedYes


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