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Volume 69 
Part 4 
Page o556  
April 2013  

Received 12 March 2013
Accepted 13 March 2013
Online 20 March 2013

Key indicators
Single-crystal X-ray study
T = 100 K
Mean [sigma](C-C) = 0.003 Å
R = 0.029
wR = 0.077
Data-to-parameter ratio = 18.0
Details
Open access

3,3-Bis(4-bromophenylsulfanyl)-1-methylpiperidin-2-one

aDepartmento de Química, Universidade Federal de São Carlos, CP 676, 13565-905 São Carlos-SP, Brazil,bChemistry Institute, University of São Paulo, 05508-000 São Paulo, SP, Brazil,cDepartment of Chemistry, University of Malaya, 50603 Kuala Lumpur, Malaysia, and dChemistry Department, Faculty of Science, King Abdulaziz University, PO Box 80203 Jeddah, Saudi Arabia
Correspondence e-mail: julio@power.ufscar.br

In the title compound, C18H17Br2NOS2, the conformation of the piperidin-2-one ring is based on a half-chair with the methylene C atom diagonally opposite the N atom being 0.649 (3) Å above the plane of the remaining five atoms (r.m.s. deviation = 0.1205 Å). The S atoms occupy axial and bisectional positions, and the dihedral angle between the benzene rings of 59.95 (11)° indicates a splayed disposition. Helical supramolecular chains along the b axis sustained by C-H...O interactions is the major feature of the crystal packing. The chains are connected into a three-dimensional architecture by C-H...Br and C-H...[pi] interactions.

Related literature

For background to the chemistry and structures of [beta]-thio-carbonyl compounds, see: Zukerman-Schpector et al. (2009[Zukerman-Schpector, J., Vinhato, E., Olivato, P. R., Rodrigues, A., Dal Colle, M., Cerqueira, C. R. Jr, Aman, H. D. & Tiekink, E. R. T. (2009). Z. Kristallogr. New Cryst. Struct. 214, 563-564.]); Vinhato (2007[Vinhato, E. (2007). PhD thesis, University of São Paulo, Brazil.]); Vinhato et al. (2011[Vinhato, E., Olivato, P. R., Rodrigues, A., Zukerman-Schpector, J. & Dal Colle, M. (2011). J. Mol. Struct. 1002, 97-106.]); Olivato et al. (2012[Olivato, P. R., Santos, J. M. M., Cerqueira, C. R. Jr, Vinhato, E., Zukerman-Schpector, J., Ng, S. W., Tiekink, E. R. T. & Dal Colle, M. (2012). J. Mol. Struct. 1028, 97-106.], 2013[Olivato, P. R., Cerqueira, C. R. Jr, Contieri, B., Santos, J. M. M. & Zukerman-Schpector, J. (2013). J. Sulfur Chem. doi:10.1080/17415993.2013.771359).]). For the synthesis, see: Olivato et al. (2013[Olivato, P. R., Cerqueira, C. R. Jr, Contieri, B., Santos, J. M. M. & Zukerman-Schpector, J. (2013). J. Sulfur Chem. doi:10.1080/17415993.2013.771359).]). For ring conformational analysis, see: Cremer & Pople (1975[Cremer, D. & Pople, J. A. (1975). J. Am. Chem. Soc. 97, 1354-1358.]).

[Scheme 1]

Experimental

Crystal data
  • C18H17Br2NOS2

  • Mr = 487.27

  • Monoclinic, P 21 /n

  • a = 7.8777 (1) Å

  • b = 9.6481 (1) Å

  • c = 24.6757 (3) Å

  • [beta] = 93.190 (1)°

  • V = 1872.57 (4) Å3

  • Z = 4

  • Cu K[alpha] radiation

  • [mu] = 7.61 mm-1

  • T = 100 K

  • 0.25 × 0.25 × 0.05 mm

Data collection
  • Agilent SuperNova (Dual, Cu at zero, Atlas) diffractometer

  • Absorption correction: multi-scan (CrysAlis PRO; Agilent, 2011[Agilent (2011). CrysAlis PRO. Agilent Technologies, Yarnton, England.]) Tmin = 0.298, Tmax = 1.000

  • 18656 measured reflections

  • 3916 independent reflections

  • 3715 reflections with I > 2[sigma](I)

  • Rint = 0.038

Refinement
  • R[F2 > 2[sigma](F2)] = 0.029

  • wR(F2) = 0.077

  • S = 1.10

  • 3916 reflections

  • 218 parameters

  • H-atom parameters constrained

  • [Delta][rho]max = 0.71 e Å-3

  • [Delta][rho]min = -1.26 e Å-3

Table 1
Hydrogen-bond geometry (Å, °)

Cg1 is the centroid of the C7-C12 ring.

D-H...A D-H H...A D...A D-H...A
C9-H9...Br2i 0.95 2.87 3.744 (2) 154
C11-H11...O1ii 0.95 2.27 3.195 (3) 163
C1-H1B...Cg1i 0.98 2.86 3.660 (3) 139
Symmetry codes: (i) [-x+{\script{3\over 2}}, y+{\script{1\over 2}}, -z+{\script{1\over 2}}]; (ii) [-x+{\script{1\over 2}}, y-{\script{1\over 2}}, -z+{\script{1\over 2}}].

Data collection: CrysAlis PRO (Agilent, 2011[Agilent (2011). CrysAlis PRO. Agilent Technologies, Yarnton, England.]); cell refinement: CrysAlis PRO; data reduction: CrysAlis PRO; program(s) used to solve structure: SIR92 (Altomare et al., 1999[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.]); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); molecular graphics: ORTEP-3 for Windows (Farrugia, 2012[Farrugia, L. J. (2012). J. Appl. Cryst. 45, 849-854.]) and DIAMOND (Brandenburg, 2006[Brandenburg, K. (2006). DIAMOND. Crystal Impact GbR, Bonn, Germany.]); software used to prepare material for publication: publCIF (Westrip, 2010[Westrip, S. P. (2010). J. Appl. Cryst. 43, 920-925.]).


Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: HG5299 ).


Acknowledgements

We thank the Brazilian agencies FAPESP, CNPq and CAPES (808/2009 to JZ-S) for financial support. CRC and BC thank CNPq for scholarships; PRO and JZ-S thank CNPq for fellowships. We also thank the Ministry of Higher Education (Malaysia) for funding structural studies through the High-Impact Research scheme (UM.C/HIR-MOHE/SC/03).

References

Agilent (2011). CrysAlis PRO. Agilent Technologies, Yarnton, 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.  [ISI] [CrossRef] [ChemPort] [details]
Brandenburg, K. (2006). DIAMOND. Crystal Impact GbR, Bonn, Germany.
Cremer, D. & Pople, J. A. (1975). J. Am. Chem. Soc. 97, 1354-1358.  [CrossRef] [ChemPort] [ISI]
Farrugia, L. J. (2012). J. Appl. Cryst. 45, 849-854.  [ISI] [CrossRef] [ChemPort] [details]
Olivato, P. R., Cerqueira, C. R. Jr, Contieri, B., Santos, J. M. M. & Zukerman-Schpector, J. (2013). J. Sulfur Chem. doi:10.1080/17415993.2013.771359).
Olivato, P. R., Santos, J. M. M., Cerqueira, C. R. Jr, Vinhato, E., Zukerman-Schpector, J., Ng, S. W., Tiekink, E. R. T. & Dal Colle, M. (2012). J. Mol. Struct. 1028, 97-106.  [ISI] [CrossRef]
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.  [CrossRef] [details]
Vinhato, E. (2007). PhD thesis, University of São Paulo, Brazil.
Vinhato, E., Olivato, P. R., Rodrigues, A., Zukerman-Schpector, J. & Dal Colle, M. (2011). J. Mol. Struct. 1002, 97-106.  [ISI] [CSD] [CrossRef] [ChemPort]
Westrip, S. P. (2010). J. Appl. Cryst. 43, 920-925.  [ISI] [CrossRef] [ChemPort] [details]
Zukerman-Schpector, J., Vinhato, E., Olivato, P. R., Rodrigues, A., Dal Colle, M., Cerqueira, C. R. Jr, Aman, H. D. & Tiekink, E. R. T. (2009). Z. Kristallogr. New Cryst. Struct. 214, 563-564.


Acta Cryst (2013). E69, o556  [ doi:10.1107/S1600536813006995 ]

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