6,6′-Dimethylsulfinyl-2,2′-bipyridine: crystal structure and Hirshfeld surface analysis

The structure of 6,6'-dimethylsulfinyl-2,2'-bipyridine (1) has been determined by a single-crystal X-ray crystallography. This compound crystallizes in the monoclinic P2(1) space group with a = 5.7922(12) angstrom, b = 8.7292(5) angstrom, c = 13.0887(16) angstrom, beta = 102.094(14)degrees and Z = 2. The molecule of 1 consists of a 2,2'-bipyridine moiety substituted in the 6 and 6' positions by dimethylsulfinyl groups. Atoms belonging to one of these two groups are disordered over two positions with an occupation of 0.600(9) for the major component. The molecular structure of 1 has been compared and discussed with several similar compounds. In the solid state, molecules of 1 are linked by two independent weak C-H center dot center dot center dot O hydrogen bonds forming the infinite simple C(4) and C(5) chains, and their combined effect is a formation of the R-4(4)(42) ring additionally stabilized by intermolecular pi center dot center dot center dot pi stacking and S=O center dot center dot center dot pi interactions. Moreover, Hirshfeld surface analysis has been used for comparison of the interactions in the crystal structure of 1 and in those of several of its simple analogues [i.e. 1-[6-(6-acetylpyridin-2-yl)pyridin-2-yl]ethanone, dimethyl 2,2'-bipyridine-6,6'-dicarboxylate, 6,6'-dimethyl-2,2'-bipyridyl and 2,2'-bipyridyl]. [GRAPHICS] .