Research Article: 1-Methyl-3,3-bis­(phenyl­sulfan­yl)piperidin-2-one

Date Published: June 01, 2012

Publisher: International Union of Crystallography

Author(s): Ignez Caracelli, Paulo R. Olivato, Carlos R. Cerqueira Jr, Jean M. M. Santos, Seik Weng Ng, Edward R. T. Tiekink.


The piperidone ring in the title compound, C18H19NOS2, is in a distorted half-chair conformation, distorted towards a twisted boat, with the central methyl­ene C atom of the propyl backbone lying 0.606 (2) Å out of the plane defined by the other five atoms (r.m.s. deviation = 0.1197 Å). One of the S-bound phenyl rings is almost perpendicular to the least-squares plane through the piperidone ring, whereas the other is splayed [dihedral angles = 75.97 (6) and 44.21 (7)°, respectively]. The most prominent feature of the crystal packing is the formation of helical supra­molecular chains along the b axis sustained by C—H⋯O inter­actions. The chains are consolidated into a three-dimensional architecture via C—H⋯π inter­actions whereby one S-bound phenyl ring accepts two C—H⋯π contacts.

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For background to β-thio-carbonyl compounds, see: Vinhato et al. (2011 ▶); Olivato et al. (2009 ▶). For related structures, see: Zukerman-Schpector et al. (2010 ▶, 2011 ▶). For ring conformational analysis, see: Cremer & Pople (1975 ▶). For the synthesis, see: Zoretic & Soja (1976 ▶).




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