Crystal structures of (N-methyl-N-phenylamino)(N-methyl-N-phenylcarbamoyl)sulfide and the corresponding disulfane

Abstract

The title compounds, (N-methyl-N-phenylamino)(N-methyl-N-phenylcarbamoyl)sulfide, C15H16N2OS, (I), and (N-methyl-N-phenylamino)(N-methyl-N-phenylcarbamoyl)disulfane, C15H16N2OS2, (II), are stable derivatives of (chlorocarbonyl)sulfenyl chloride and (chlorocarbonyl)disulfanyl chloride, respectively. The torsion angle about the S—S bond in (II) is −92.62 (6)°, which is close to the theoretical value of 90°. In the crystal of (II), non-classical intermolecular C—H...O hydrogen bonds form centrosymmetric cyclic dimers [graph set R22(10)], while inter-dimer C—H...S interactions generate chains extending along the b axis.

Keywords

• crystal structure
• organosulfur chemistry
• sulfide
• disulfane
• hydrogen bonding