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

• Main Authors: Sevim Türktekin Çelikesir, Ömer Çelik, Senem Akkoç, İlhan Özer İlhan, Yetkin Gök, Mehmet Akkurt
• Format: Article
• Language: English
• Published: International Union of Crystallography 2015-01-01
• Series: Acta Crystallographica Section E: Crystallographic Communications
• Subjects: crystal structure; 1,3-bis(4-methylbenzyl)-1H-3,1-benzimidazol-3-ium bromide monohydrate; benzimidazolium salts; N-heterocyclic carbenes; hydrogen bonds; aromatic π–π stacking interactions
• Online Access: http://scripts.iucr.org/cgi-bin/paper?S2056989014025857

In the title hydrated symetrically substituted 1,3-bis(4-methylbenzyl)benzimidazolium salt, C23H23N2+·Br−·H2O, the dihedral angles between the benzimidazole ring system (r.m.s. deviation = 0.003 Å) and the pendant benzene rings are 73.18 (16) and 77.52 (16)°. 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...O hydrogen bond and the water molecule forms O—H...Br hydrogen bonds. Together, these interactions lead to [010] chains. The packing is consolidated by C—H...Br hydrogen bonds and aromatic π–π stacking interactions [centroid–centroid distances = 3.5401 (17) and 3.8815 (18) Å], generating a three-dimensional network.