The title N-heterocyclic carbene derivative, C23H30N5+center dot Br-center dot 0.25H(2)O, was synthesized using microwave heating and was characterized by H-1 and C-13 NMR spectroscopy and a single-crystal X-ray diffraction study. The structure of the title compound are stabilized by a network of intra-and intermolecular C-H center dot center dot center dot Br hydrogen-bonding interactions. The crystal structure is further stabilized by pi-pi stacking interactions between benzene and imidazole fragment rings of parallel benzo[d] imidazole rings, with a separation of 3.486 (3) angstrom between the centroids of the benzene and imidazole rings. There is also an intermolecular C-H center dot center dot center dot pi interaction in the crystal structure. The C-N bond lengths for the central benzimidazole ring are shorter than the average single C-N bond, thus showing varying degrees of double-bond character and indicating partial electron delocalization within the C-N-C-N-C fragment. The isopropyl group is disordered over two sites with occupancies of 0.792 (10) and 0.208 (10).
C1 [Arslan, Hakan] Fayetteville State Univ, Dept Nat Sci, Fayetteville, NC 28301 USA.
[Arslan, Hakan] Mersin Univ, Dept Chem, Fac Pharm, TR-33169 Mersin, Turkey.
[VanDerveer, Don] Clemson Univ, Dept Chem, Clemson, SC 29634 USA.
[Demir, Serpil; Oezdemir, Ismail] Inonu Univ, Dept Chem, Fac Sci & Arts, TR-44280 Malatya, Turkey.
[Cetinkaya, Bekir] Ege Univ, Dept Chem, Fac Sci, TR-35100 Bornova, Turkey.