Crystal structure of 1,3-bis(4-methylbenzyl)-1H-1,3-benzimidazol-3-ium bromide monohydrate

Celikesir S. T. , Celik O., Akkoc S., Ilhan I. O. , GÖK Y., AKKURT M.

ACTA CRYSTALLOGRAPHICA SECTION E-CRYSTALLOGRAPHIC COMMUNICATIONS, vol.71, 2015 (Peer-Reviewed Journal) identifier identifier identifier

  • Publication Type: Article / Article
  • Volume: 71
  • Publication Date: 2015
  • Doi Number: 10.1107/s2056989014025857
  • Journal Indexes: Emerging Sources Citation Index, Scopus
  • Keywords: crystal structure, 1,3-bis(4-methylbenzyl)-1H-3,1-benzimidazol-3-ium bromide monohydrate, benzimidazolium salts, N-heterocyclic carbenes, hydrogen bonds, aromatic pi-pi stacking interactions, CATALYTIC-ACTIVITIES, CARBENE, COMPLEXES


In the title hydrated symetrically substituted 1,3-bis(4-methyl-benzyl) benzimidazolium salt, C23H23N2+center dot Br-center dot H2O, the dihedral angles between the benzimidazole ring system (r.m.s. deviation = 0.003 angstrom) and the pendant benzene rings are 73.18 (16) and 77.52 (16)degrees. Both benzene rings lie to the same side of the benzimidazole ring system, giving the cation an overall U-shape. In the crystal, the cation is linked to the water molecule by a short C-H center dot center dot center dot O hydrogen bond and the water molecule forms O-H center dot center dot center dot Br hydrogen bonds. Together, these interactions lead to [010] chains. The packing is consolidated by C-H center dot center dot center dot Br hydrogen bonds and aromatic pi-pi stacking interactions [centroid-centroid distances = 3.5401 (17) and 3.8815 (18) angstrom], generating a three-dimensional network.