1-Methyl-3,3-bis(phenylsulfanyl)- piperidin-2-one Ignez Caracelli, a * Paulo R. Olivato, b Carlos R. Cerqueira Jr, b Jean M. M. Santos, b Seik Weng Ng c,d and Edward R. T. Tiekink c a BioMat – Departamento de Fı ´sica, Universidade Federal de Sa ˜o Carlos, 13565-905 Sa ˜o Carlos, SP, Brazil, b Chemistry Institute, Universidade de Sa ˜o Paulo, 05508-000 Sa ˜o Paulo, SP, Brazil, c Department of Chemistry, University of Malaya, 50603 Kuala Lumpur, Malaysia, and d Chemistry Department, Faculty of Science, King Abdulaziz University, PO Box 80203 Jeddah, Saudi Arabia Correspondence e-mail: ignez@ufscar.br Received 26 April 2012; accepted 10 May 2012 Key indicators: single-crystal X-ray study; T = 100 K; mean (C–C) = 0.003 A ˚ ; R factor = 0.025; wR factor = 0.067; data-to-parameter ratio = 13.8. The piperidone ring in the title compound, C 18 H 19 NOS 2 , 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) A ˚ out of the plane defined by the other five atoms (r.m.s. deviation = 0.1197 A ˚ ). 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—HO interactions. The chains are consolidated into a three-dimensional architecture via C—H interactions whereby one S-bound phenyl ring accepts two C—H contacts. Related literature For background to -thio-carbonyl compounds, see: Vinhato et al. (2011); Olivato et al. (2009). For related structures, see: Zukerman-Schpector et al. (2010, 2011). For ring conforma- tional analysis, see: Cremer & Pople (1975). For the synthesis, see: Zoretic & Soja (1976). Experimental Crystal data C 18 H 19 NOS 2 M r = 329.48 Orthorhombic, P2 1 2 1 2 1 a = 8.2103 (1) A ˚ b = 9.8329 (1) A ˚ c = 20.3686 (2) A ˚ V = 1644.38 (3) A ˚ 3 Z =4 Cu K radiation = 2.93 mm 1 T = 100 K 0.35 0.30 0.25 mm Data collection Agilent SuperNova Dual (Cu at zero) diffractometer with an Atlas detector Absorption correction: multi-scan (CrysAlis PRO; Agilent, 2010) T min = 0.427, T max = 0.585 4452 measured reflections 2769 independent reflections 2728 reflections with I >2(I) R int = 0.016 Refinement R[F 2 >2(F 2 )] = 0.025 wR(F 2 ) = 0.067 S = 1.09 2769 reflections 200 parameters H-atom parameters constrained Á max = 0.19 e A ˚ 3 Á min = 0.32 e A ˚ 3 Absolute structure: Flack (1983), 818 Friedel pairs Flack parameter: 0.024 (14) Table 1 Hydrogen-bond geometry (A ˚ , ). Cg1 is the centroid of the C7–C12 ring. D—HA D—H HA DA D—HA C11—H11O1 i 0.95 2.32 3.237 (3) 163 C6—H6bCg1 ii 0.98 2.95 3.606 (2) 125 C14—H14Cg1 iii 0.95 2.96 3.544 (2) 121 Symmetry codes: (i) x þ 1; y 1 2 ; z þ 3 2 ; (ii) x þ 1; y 1 2 ; z þ 1 2 ; (iii) x; y 1 2 ; z þ 3 2 . Data collection: CrysAlis PRO (Agilent, 2010); cell refinement: CrysAlis PRO; data reduction: CrysAlis PRO; program(s) used to solve structure: SIR92 (Altomare et al. , 1999); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 (Farrugia, 1997), DIAMOND (Brandenburg, 2006) and MarvinSketch (ChemAxon, 2009); software used to prepare material for publication: publCIF (Westrip, 2010). The authors thank the Brazilian agencies FAPESP, CNPq (fellowships to IC and PRO, and scholarships for CRCJ and JMMS) and CAPES (grant No. 808/2009 to IC) for financial support. The authors also thank the Ministry of Higher Education (Malaysia) for funding structural studies through the High-Impact Research scheme (UM.C/HIR/MOHE/SC/ 12). Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: HG5220). References Agilent (2010). CrysAlis PRO. Agilent Technologies, Yarnton, Oxfordshire, England. Altomare, A., Burla, M. C., Camalli, M., Cascarano, G. L., Giacovazzo, C., Guagliardi, A., Moliterni, A. G. G., Polidori, G. & Spagna, R. (1999). J. Appl. Cryst. 32, 115–119. Brandenburg, K. (2006). DIAMOND. Crystal Impact GbR, Bonn, Germany. ChemAxon (2009). MarvinSketch. URL: www.chemaxon.com. Cremer, D. & Pople, J. A. (1975). J. Am. Chem. Soc. 97, 1354–1358. Farrugia, L. J. (1997). J. Appl. Cryst. 30, 565. Flack, H. D. (1983). Acta Cryst. A39, 876–881. Olivato, P. R., Domingues, N. L. C., Mondino, M. G., Tormena, C. F., Rittner, R. & Dal Colle, M. (2009). J. Mol. Struct. 920, 393–400. organic compounds Acta Cryst. (2012). E68, o1793–o1794 doi:10.1107/S1600536812021277 Caracelli et al. o1793 Acta Crystallographica Section E Structure Reports Online ISSN 1600-5368