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Open Access Crystal structures of three (trichloromethyl)(carbamoyl)disulfanes

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The present paper reports crystallographic studies on three related compounds that were of interest as precursors for synthetic and mechanistic work in organosulfur chemistry, as well as to model nitrogen-protecting groups: (N-methylcarbamoyl)(trichloromethyl)disulfane, C3H4Cl3NOS2, (1), (N-benzylcarbamoyl)(trichloromethyl)disulfane, C9H8Cl3NOS2, (2), and (N-methyl-N-phenylcarbamoyl)(trichloromethyl)disulfane, C9H8Cl3NOS2, (3). Their molecular structures, with similar bond lengths and angles for the CCl3SS(C=O)N moieties, are confirmed. Compounds (1) and (3) both crystallized with two independent molecules in the asymmetric unit. Classical hydrogen bonding, as well as chlorine-dense regions, are evident in the crystal packing for (1) and (2). In the crystal of (1), molecules are linked via N—H...O hydrogen bonds forming chains along [110], which are linked by short Cl...Cl and S...O contacts forming sheets parallel to (001). In the crystal of (2), molecules are linked via N—H...O hydrogen bonds forming chains along [001], which in turn are linked by pairs of short O...Cl contacts forming ribbons along the c-axis direction. In the crystal of (3), there are no classical hydrogen bonds present and the chlorine-dense regions observed in (1) and (2) are lacking.
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Document Type: Research Article

Affiliations: Department of Chemistry, University of Minnesota, Minneapolis, MN 55455, USA

Publication date: January 1, 2015

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