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C—I…N and C—I…π halogen bonding in the structures of 1‐benzyliodoimidazole derivatives
Author(s) -
Nwachukwu Chideraa I.,
Bowling Nathan P.,
Bosch Eric
Publication year - 2017
Publication title -
acta crystallographica section c
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.304
H-Index - 17
ISSN - 2053-2296
DOI - 10.1107/s2053229616018702
Subject(s) - halogen , halogen bond , intermolecular force , imidazole , benzimidazole , molecule , chemistry , crystallography , zigzag , stereochemistry , hydrogen bond , organic chemistry , mathematics , geometry , alkyl
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‐1 H ‐imidazole, C 10 H 9 IN 2 , (1), 1‐benzyl‐4‐iodo‐1 H ‐imidazole, C 10 H 9 IN 2 , (2), and 1‐benzyl‐2‐iodo‐1 H ‐benzimidazole, C 14 H 11 IN 2 , (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.