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Volume 69 
Part 1 
Page o21  
January 2013  

Received 26 November 2012
Accepted 28 November 2012
Online 5 December 2012

Key indicators
Single-crystal X-ray study
T = 173 K
Mean [sigma](C-C) = 0.002 Å
R = 0.037
wR = 0.098
Data-to-parameter ratio = 19.7
Details
Open access

(±)-3-Benzyloxy-1-(4-methoxybenzyl)piperidine-2-thione

aMolecular Sciences Institute, School of Chemistry, University of the Witwatersrand, PO Wits 2050, Johannesburg, South Africa
Correspondence e-mail: joseph.michael@wits.ac.za

The title molecule, C20H23NO2S, adopts a twisted conformation in which the two aromatic rings connected to the central piperidine ring are orientated trans to each other. An intramolecular C-H...S contact occurs. In the crystal, C-H...[pi] and C-H...O interactions act to stabilize the structure in three dimensions.

Related literature

For the use of related piperidinethiones in the synthesis of febrifugine analogues, see: Michael et al. (2006[Michael, J. P., de Koning, C. B. & Pienaar, D. P. (2006). Synlett, pp. 383-386.]). For information on the biological activity of febrifugine, see: Murata et al. (1998[Murata, K., Takano, F., Fushiya, S. & Oshima, Y. (1998). J. Nat. Prod. 61, 729-733.]).

[Scheme 1]

Experimental

Crystal data
  • C20H23NO2S

  • Mr = 341.45

  • Orthorhombic, P b c a

  • a = 18.371 (3) Å

  • b = 10.4844 (15) Å

  • c = 18.467 (3) Å

  • V = 3556.9 (9) Å3

  • Z = 8

  • Mo K[alpha] radiation

  • [mu] = 0.19 mm-1

  • T = 173 K

  • 0.47 × 0.28 × 0.05 mm

Data collection
  • Bruker APEXII CCD area-detector diffractometer

  • 22717 measured reflections

  • 4286 independent reflections

  • 2949 reflections with I > 2[sigma](I)

  • Rint = 0.046

Refinement
  • R[F2 > 2[sigma](F2)] = 0.037

  • wR(F2) = 0.098

  • S = 1.01

  • 4286 reflections

  • 218 parameters

  • H-atom parameters constrained

  • [Delta][rho]max = 0.26 e Å-3

  • [Delta][rho]min = -0.26 e Å-3

Table 1
Hydrogen-bond geometry (Å, °)

Cg1 is the centroid of the C16-C21 ring.

D-H...A D-H H...A D...A D-H...A
C7-H7A...S1 0.99 2.54 3.0760 (16) 114
C13-H13...O2i 0.95 2.59 3.4913 (19) 158
C6-H6B...Cg1i 0.99 2.54 3.5066 (19) 165
C14-H14A...Cg1ii 0.98 2.61 3.455 (2) 144
Symmetry codes: (i) [-x, y-{\script{1\over 2}}, -z+{\script{3\over 2}}]; (ii) -x, -y, -z+1.

Data collection: APEX2 (Bruker, 2005[Bruker (2005). APEX2 and SAINT-NT. Bruker AXS Inc., Madison, Wisconsin, USA.]); cell refinement: SAINT-NT (Bruker, 2005[Bruker (2005). APEX2 and SAINT-NT. Bruker AXS Inc., Madison, Wisconsin, USA.]); data reduction: SAINT-NT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); 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 SCHAKAL99 (Keller, 1999[Keller, E. (1999). SCHAKAL99. University of Freiberg, Germany.]); software used to prepare material for publication: WinGX (Farrugia, 2012[Farrugia, L. J. (2012). J. Appl. Cryst. 45, 849-854.]) and PLATON (Spek, 2009[Spek, A. L. (2009). Acta Cryst. D65, 148-155.]).


Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: GO2079 ).


Acknowledgements

This work was supported by the University of the Witwatersrand and the National Research Foundation, Pretoria (grant number 78837).

References

Bruker (2005). APEX2 and SAINT-NT. Bruker AXS Inc., Madison, Wisconsin, USA.
Farrugia, L. J. (2012). J. Appl. Cryst. 45, 849-854.  [ISI] [CrossRef] [ChemPort] [details]
Keller, E. (1999). SCHAKAL99. University of Freiberg, Germany.
Michael, J. P., de Koning, C. B. & Pienaar, D. P. (2006). Synlett, pp. 383-386.  [ISI] [CrossRef]
Murata, K., Takano, F., Fushiya, S. & Oshima, Y. (1998). J. Nat. Prod. 61, 729-733.  [ISI] [CrossRef] [ChemPort] [PubMed]
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.  [CrossRef] [details]
Spek, A. L. (2009). Acta Cryst. D65, 148-155.  [ISI] [CrossRef] [details]


Acta Cryst (2013). E69, o21  [ doi:10.1107/S1600536812048854 ]

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