2,2′-Dithiodianiline: a redetermination at 100 K

• Main Authors: Jia Hao Goh, Hoong-Kun Fun, M. Babu, B. Kalluraya
• Format: Article
• Language: English
• Published: International Union of Crystallography 2010-02-01
• Series: Acta Crystallographica Section E
• Online Access: http://scripts.iucr.org/cgi-bin/paper?S1600536810000024

Structural studies of the title compound [systematic name: 2,2′-(disulfanediyl)dianiline], C12H12N2S2, were previously performed at room temperature [Gomes de Mesquita (1967). Acta Cryst. 23, 671; Lee & Bryant (1970). Acta Cryst. B26, 1729; Ribar et al. (1975). Bull. Yugoslav. Crystallogr. Centre, A10, 68]. The results of the current redetermination allow a clarification of the nature of the intra- and intermolecular N—H...S hydrogen bonding described in the literature for this compound. On cooling to 100 K, the unit cell contracts most in the c axis, and it changes rather less in the directions involving the strongly hydrogen-bonded chains, which are the a and b axes. In the crystal structure, N—H...N hydrogen bonds link neighbouring molecules into two-dimensional frameworks parallel to the ab plane. An additional intermolecular N—H...S hydrogen bond has also been established, based on freely refined H-atom positions. Intermolecular C—H...π interactions further stabilize the crystal structure.