Co-crystallization of sym-triiodo-trifluorobenzene with bipyridyl donors

Consistent formation of two instead of anticipated three N⋯I halogen bonds

André C B Lucassen, Amir Karton, Gregory Leitus, Linda J W Shimon, Jan M L Martin, Milko van der Boom

Research output: Contribution to journalArticle

63 Citations (Scopus)

Abstract

The potential triple-halogen-bond acceptor, sym-triiodo-trifluorobenzene IFB (1), has been co-crystallized with a series of bipyridyl derivatives (2-4) to gain insight to the factors controlling formation of multiple halogen bonds with a single aromatic system. Co-crystals 5-7 were obtained that consistently contained two N⋯I halogen bonds. The reluctance to the formation of a supramolecular assembly having a third N⋯I halogen bond does not depend on the size of the bispyridine donor systems (2-4). Apparently, there are limitations to the number of halogen bonds that can be formed with a single aromatic halogen donor. The solid-state structure of co-crystal (5) contains short I⋯F contacts of 2.96 and 3.05 A. DFT calculations were performed at the PBE0/(apc1-aSDBDZ)//PBEO/(pc1-SDBDZ) level of theory to investigate the nature of the interaction between the pyridine nitrogen and IFB (1). These calculations reveal a weakening of N⋯I interactions as more pyridine moieties coordinate to the IFB (1), which might be a contributing factor to the consistent formation of two rather than three N⋯I halogen bonds.

Original languageEnglish
Pages (from-to)386-392
Number of pages7
JournalCrystal Growth and Design
Volume7
Issue number2
DOIs
Publication statusPublished - Feb 2007

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2,2'-Dipyridyl
Halogens
Crystallization
Pyridine
halogens
crystallization
Crystals
Discrete Fourier transforms
Nitrogen
Derivatives
pyridines
reluctance
crystals
assembly
interactions
solid state
nitrogen

ASJC Scopus subject areas

  • Chemistry(all)
  • Materials Science(all)
  • Condensed Matter Physics

Cite this

Co-crystallization of sym-triiodo-trifluorobenzene with bipyridyl donors : Consistent formation of two instead of anticipated three N⋯I halogen bonds. / Lucassen, André C B; Karton, Amir; Leitus, Gregory; Shimon, Linda J W; Martin, Jan M L; van der Boom, Milko.

In: Crystal Growth and Design, Vol. 7, No. 2, 02.2007, p. 386-392.

Research output: Contribution to journalArticle

Lucassen, André C B ; Karton, Amir ; Leitus, Gregory ; Shimon, Linda J W ; Martin, Jan M L ; van der Boom, Milko. / Co-crystallization of sym-triiodo-trifluorobenzene with bipyridyl donors : Consistent formation of two instead of anticipated three N⋯I halogen bonds. In: Crystal Growth and Design. 2007 ; Vol. 7, No. 2. pp. 386-392.
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