3-Hy­droxy-1-(4-meth­oxy­benz­yl)piperidin-2-one

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

doi:10.1107/S1600536812049501

Volume 69
Part 1
Page o51
January 2013

Received 29 November 2012
Accepted 3 December 2012
Online 8 December 2012

Key indicators
Single-crystal X-ray study
T = 173 K
Mean (C-C) = 0.002 Å
R = 0.042
wR = 0.124
Data-to-parameter ratio = 18.3
Details

3-Hydroxy-1-(4-methoxybenzyl)piperidin-2-one

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 compound, C₁₃H₁₇NO₃, adopts a conformation in which the aromatic ring and the mean plane of the piperidine ring are almost perpendicular to each other [dihedral angle = 79.25 (6)°]. The presence of the carbonyl group alters the conformation of the piperidine ring from a chair to a twisted half-chair conformation. In the crystal, pairs of strong O-HO hydrogen bonds link the molecules into inversion dimers. Weak C-HO interactions extend the hydrogen-bonding network into three dimensions.

Related literature

For the use of related lactams in the synthesis of febrifugine analogues, see: Michael et al. (2006). For information on the biological activity of febrifugine, a quinazoline alkaloid with potent antimalarial activity, see: Murata et al. (1998). For the use of chiral oxaziridines in asymmetric hydroxylation, see: Davis et al. (1990). For the conformation of six-membered rings, see: Boeyens (1978).

Experimental

Crystal data

C₁₃H₁₇NO₃
M_r = 235.28
Monoclinic, P 2₁ /c
a = 12.980 (3) Å
b = 7.6143 (17) Å
c = 12.189 (3) Å
= 90.497 (5)°
V = 1204.6 (5) Å³
Z = 4
Mo K radiation
= 0.09 mm^-1
T = 173 K
0.32 × 0.26 × 0.18 mm

Data collection

Bruker APEXII CCD diffractometer
8378 measured reflections
2895 independent reflections
2271 reflections with I > 2(I)
R_int = 0.027

Refinement

R[F² > 2(F²)] = 0.042
wR(F²) = 0.124
S = 1.08
2895 reflections
158 parameters
H atoms treated by a mixture of independent and constrained refinement
_max = 0.52 e Å^-3
_min = -0.22 e Å^-3

Table 1
Hydrogen-bond geometry (Å, °)

D-HA	D-H	HA	DA	D-HA
O2-H2O1ⁱ	0.96 (2)	1.84 (2)	2.7708 (16)	161.6 (19)
C6-H6BO1ⁱⁱ	0.99	2.43	3.3142 (17)	148
C14-H14BO2ⁱⁱⁱ	0.98	2.52	3.449 (2)	158
Symmetry codes: (i) -x, -y, -z+1; (ii) $[x, -y+{\script{1\over 2}}, z-{\script{1\over 2}}]$ ; (iii) -x+1, -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: BH2468 ).

Acknowledgements

This work was supported by the University of the Witwatersrand and the National Research Foundation, Pretoria (grant No. 78837).

References

Boeyens, J. C. A. (1978). J. Cryst. Mol. Struct. 8, 317-320.
Bruker (2005). APEX2 and SAINT-NT. Bruker AXS Inc., Madison, Wisconsin, USA.
Davis, F. A., Sheppard, A. C., Chen, B.-C. & Haque, M. S. (1990). J. Am. Chem. Soc. 112, 6679-6690.
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