C - I...N and C - I...π halogen bonding in the structures of 1-benzyliodoimidazole derivatives

Abstract

Halogen bonding is a well-established and intensively studied intermolecular interaction that has also been used in the preparation of functional materials. While polyfluoroiodo- and polyfluorobromobenzenes have been widely used as aromatic halogen-bond donors, there have been very few studies of iodoimidazoles with regard to halogen bonding. We describe here the X-ray structures of three iodoimidazole derivatives, namely 1-benzyl-2-iodo-1H-imidazole, C10H9IN2, (1), 1-benzyl-4-iodo-1H-imidazole, C10H9IN2, (2), and 1-benzyl-2-iodo-1H-benzimidazole, C14H11IN2, (3), and the halogen bonds that dominate the intermolecular interactions in each of these three structures. The three-dimensional structure of (1) is dominated by a strong C - I...N halogen bond, with an N...I distance of 2.8765?(2)?Å, that connects the molecules into one-dimensional zigzag ribbons of molecules. In contrast, the three-dimensional structures of (2) and (3) both feature C - I...π halogen-bonded dimers.The role of halogen bonding, i.e. C - I...N and C - I...π, as a major intermolecular force is investigated in the crystal structures of three iodoimidazole derivatives.

Department(s)

Chemistry and Biochemistry

Document Type

Article

DOI

https://doi.org/10.1107/S2053229616018702

Keywords

computational chemistry, crystal structure, halogen bonding, halogen-bonded dimer, intermolecular interactions, iodoimidazole, molecular electrostatic potential

Publication Date

1-1-2017

Journal Title

Acta Crystallographica Section C: Structural Chemistry

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