Mono- and difunctional furan-based 1,2,3,5-dithiadiazolyl radicals; preparation and solid state structures of 2,5-[(S2N2C)OC4H2(CN2S2)] and 2,5-[(S2N2C)OC4H2(CN)]

• Published in: Canadian journal of chemistry Vol. 70; no. 3; pp. 919 - 925
• Main Authors: Cordes, A. Wallace, Chamchoumis, Charles M, Hicks, Robin G, Oakley, Richard T, Young, Kelly M, Haddon, Robert C
• Format: Journal Article
• Language: English
• Published: Ottawa, Canada NRC Research Press 01.03.1992
• ISSN: 0008-4042; 1480-3291
• DOI: 10.1139/v92-123

The preparation and solid state characterization of the bifunctional radical furan-2,5-bis(1,2,3,5-dithiadiazolyl) 2,5-[(S 2 N 2 C)OC 4 H 2 (CN 2 S 2 )] and the related monofunctional radical 2-cyanofuran-5-(1,2,3,5-dithiadiazolyl) 2,5-[(S 2 N 2 C)OC 4 H 2 (CN)] are described. The crystal structure of 2,5-[(S 2 N 2 C)OC 4 H 2 (CN 2 S 2 )] is orthorhombic, space group Pna2 1 , and consists of interleaved arrays of dimers, for which the mean interannular contact is 3.137 Å. The crystal structure of the monofunctional radical 2,5-[(S 2 N 2 C)OC 4 H 2 (CN)] is monoclinic, space group P2 1 /n, and consists of a ribbon-like network of dimers (mean interannular interconnected by close head-to-tail contacts. The dimer units form stacks parallel to z, with a mean interdimer separation of 3.956 Å. The similarities and differences between these two crystal structures and those of related benzene-substituted systems are discussed. Keywords: dithiadiazolyl radicals, furan-based diradicals, cyanofuran-based radicals, radical dimers, crystal structures.