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

Pienaar, D.P.; Khorasani, S.; de Koning, C.B.; Michael, J.P.

doi:10.1107/S1600536812048854

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 (C-C) = 0.002 Å
R = 0.037
wR = 0.098
Data-to-parameter ratio = 19.7
Details

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

Daniel P. Pienaar,^a Sanaz Khorasani,^a Charles B. de Koning ^a and Joseph P. Michael ^a ^*

^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-HS contact occurs. In the crystal, C-H [pi] and C-HO 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). For information on the biological activity of febrifugine, see: Murata et al. (1998).

Experimental

Crystal data

C₂₀H₂₃NO₂S
M_r = 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 radiation
= 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(I)
R_int = 0.046

Refinement

R[F² > 2(F²)] = 0.037
wR(F²) = 0.098
S = 1.01
4286 reflections
218 parameters
H-atom parameters constrained
_max = 0.26 e Å^-3
_min = -0.26 e Å^-3

Table 1
Hydrogen-bond geometry (Å, °)

Cg1 is the centroid of the C16-C21 ring.

D-HA	D-H	HA	DA	D-HA
C7-H7AS1	0.99	2.54	3.0760 (16)	114
C13-H13O2ⁱ	0.95	2.59	3.4913 (19)	158
C6-H6BCg1ⁱ	0.99	2.54	3.5066 (19)	165
C14-H14ACg1ⁱⁱ	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); cell refinement: SAINT-NT (Bruker, 2005); data reduction: SAINT-NT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 for Windows (Farrugia, 2012) and SCHAKAL99 (Keller, 1999); software used to prepare material for publication: WinGX (Farrugia, 2012) and PLATON (Spek, 2009).

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.
Keller, E. (1999). SCHAKAL99. University of Freiberg, Germany.
Michael, J. P., de Koning, C. B. & Pienaar, D. P. (2006). Synlett, pp. 383-386.
Murata, K., Takano, F., Fushiya, S. & Oshima, Y. (1998). J. Nat. Prod. 61, 729-733.
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.
Spek, A. L. (2009). Acta Cryst. D65, 148-155.

organic compounds