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The role of functional nitro and cyano groups in the self-assembly of 1,3-dithiole-2-thione-halogen adducts

Skabara, Peter and Kanibolotsky, Alexander and Render, Simon and Berridge, Rory and Crouch, David J. and Bricklebank, Neil and Coles, Simon J. and Gelbrich, Thomas and Hursthouse, M. B. (2007) The role of functional nitro and cyano groups in the self-assembly of 1,3-dithiole-2-thione-halogen adducts. Heteroatom Chemistry, 18 (2). pp. 176-184. ISSN 1042-7163

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Abstract

The synthesis of five new dihalogen/interhalogen charge transfer adducts featuring cyano and nitro functionalized 1,3-dithiole-2-thiones have been prepared and characterized by x-ray crystallography. The structures feature a complex series of intermolecular close contacts between heteroatoms, as well as hydrogen bonding, to give highly ordered, polymeric assemblies. The adduct 4.IBr crystallizes in a noncentrosymmetric chiral space group and features a stack of molecules assembled through hydrogen bonds. The functional groups of all adducts participate in networks of close contacts, but do not affect the coordination environment of the dihalogen/interhalogen species.