5,5′-Bis[(1H-imidazol-1-yl)methyl]-2,2′-bipyridine methanol disolvate

The title compound, C18H16N6·2CH3OH, was prepared by the reaction of 5,5′-bis(bromomethyl)-2,2′-bipyridine with imidazole. The main molecule lies on an inversion center located at the mid-point of the C—C bond joining the two pyridine rings. The asymmetric unit therefore contains one half-molecule and one methanol solvent molecule. The dihedral angle between the pyridine and imidazole rings is 72.32 (5)°. In the crystal, weak intermolecular O—H⋯N, C—H⋯N and C—H⋯O hydrogen bonds contribute to the stabilization of the packing.

The title compound, C 18 H 16 N 6 Á2CH 3 OH, was prepared by the reaction of 5,5 0 -bis(bromomethyl)-2,2 0 -bipyridine with imidazole. The main molecule lies on an inversion center located at the mid-point of the C-C bond joining the two pyridine rings. The asymmetric unit therefore contains one half-molecule and one methanol solvent molecule. The dihedral angle between the pyridine and imidazole rings is 72.32 (5) . In the crystal, weak intermolecular O-HÁ Á ÁN, C-HÁ Á ÁN and C-HÁ Á ÁO hydrogen bonds contribute to the stabilization of the packing.

Comment
The title compound was prepared to use as a multi-dentate ligand in the formation of metallosupramolecules in line with similar previously reported compounds (Sambrook et al., 2006;Zang et al., 2010).
In the title compound (Scheme 1, Fig. 1), two pyridine rings are coplanar because the title compound lies on a crystallographic inversion center. The dihedral angle between the pyridine and imidazole rings is 72.32 (5)°. All the bond lengths are within normal values (Allen et al., 1987).
In the crystal structure, as shown in Fig. 2, weak intermolecular O-H···N, C-H···N and C-H···O hydrogen bonds are observed (Table 1). These intermolecular interactions may be contribute to the stabilization of the packing.

Experimental
A mixture of imidazole (0.120 g, 1.76 mmol) and potassium hydroxide (0.440 g, 7.84 mmol) in DMSO (10 ml) was stirred for 1 h. A DMSO solution (20 ml) of 5,5'-bis(bromomethyl)-2,2'-bipyridine (0.30 g, 0.88 mmol) was slowly added and the solution stirred for 6 h at room temperature. After water (100 ml) was added, the reaction mixture was extracted with chloroform (3×100 ml), washed with water and then dried over anhydrous MgSO 4 . The solvent was removed to give the title compound in 63% yield. X-ray quality single crystals were obtained by slow evaporation of a solution in MeOH.