π-stacking and C-X...D (X = H, NO2; D = O, π) interactions in the crystal network of both C-H...N and π-stacked dimers of 1,2-bis(4-bromophenyl)-1H-benzimidazole and 2-(4-bromophenyl)-1-(4-nitrophenyl)-1H-benzimidazole

Acta Crystallogr C Struct Chem. 2014 Jan;70(Pt 1):55-9. doi: 10.1107/S2053229613033329. Epub 2013 Dec 21.

Abstract

Molecules of 1,2-bis(4-bromophenyl)-1H-benzimidazole, C19H12Br2N2, (I), and 2-(4-bromophenyl)-1-(4-nitrophenyl)-1H-benzimidazole, C19H12BrN3O2, (II), are arranged in dimeric units through C-H...N and parallel-displaced π-stacking interactions favoured by the appropriate disposition of N- and C-bonded phenyl rings with respect to the mean benzimidazole plane. The molecular packing of the dimers of (I) and (II) arises by the concurrence of a diverse set of weak intermolecular C-X...D (X = H, NO2; D = O, π) interactions.

Keywords: crystal structure; hydrogen bonding; phenylbenzimidazole; supramolecular structures; π-stacking.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Benzimidazoles / chemistry*
  • Hydrogen Bonding
  • Models, Molecular
  • Nitro Compounds / chemistry*

Substances

  • 2-(4-bromophenyl)-1-(4-nitrophenyl)-1H-benzimidazole
  • Benzimidazoles
  • Nitro Compounds
  • benzimidazole