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Volume 67 
Part 9 
Page o2409  
September 2011  

Received 5 August 2011
Accepted 19 August 2011
Online 27 August 2011

Key indicators
Single-crystal X-ray study
T = 296 K
Mean [sigma](C-C) = 0.002 Å
R = 0.045
wR = 0.136
Data-to-parameter ratio = 22.7
Details
Open access

(2,6-Difluorophenyl)(4-methylpiperidin-1-yl)methanone

aSchool of Pharmaceutical Sciences, Universiti Sains Malaysia, 11800 USM, Penang, Malaysia,bSchool of Chemical Sciences, Universiti Sains Malaysia, 11800 USM, Penang, Malaysia, and cX-ray Crystallography Unit, School of Physics, Universiti Sains Malaysia, 11800 USM, Penang, Malaysia
Correspondence e-mail: hkfun@usm.my

In the title compound, C13H15F2NO, the piperidine ring adopts a chair conformation. The dihedral angle between the least-squares plane of the piperidine ring and the benzene ring is 48.75 (7)°. In the crystal structure, the molecules are connected via C-H...O hydrogen bonds, forming a zigzag chain along the b axis.

Related literature

For the biological applications of piperidine derivatives, see: Waelbroeck et al. (1992[Waelbroeck, M., Camus, J., Tastenoy, M. & Christophe, J. (1992). Br. J. Pharmacol. 105, 97-102.]); El Hadri et al. (1995[El Hadri, A., Maldivi, P., Leclerc, G. & Rocher, J.-P. (1995). Bioorg. Med. Chem. 3, 1183-1201.]). For puckering parameters, see: Cremer & Pople (1975[Cremer, D. & Pople, J. A. (1975). J. Am. Chem. Soc. 97, 1354-1358.]).

[Scheme 1]

Experimental

Crystal data
  • C13H15F2NO

  • Mr = 239.26

  • Monoclinic, P 21 /c

  • a = 9.1807 (7) Å

  • b = 10.9910 (8) Å

  • c = 13.2477 (8) Å

  • [beta] = 115.582 (4)°

  • V = 1205.71 (15) Å3

  • Z = 4

  • Mo K[alpha] radiation

  • [mu] = 0.10 mm-1

  • T = 296 K

  • 0.43 × 0.38 × 0.19 mm

Data collection
  • Bruker APEXII DUO CCD area-detector diffractometer

  • Absorption correction: multi-scan (SADABS; Bruker, 2009[Bruker (2009). APEX2, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.]) Tmin = 0.956, Tmax = 0.981

  • 11030 measured reflections

  • 3513 independent reflections

  • 2617 reflections with I > 2[sigma](I)

  • Rint = 0.018

Refinement
  • R[F2 > 2[sigma](F2)] = 0.045

  • wR(F2) = 0.136

  • S = 1.06

  • 3513 reflections

  • 155 parameters

  • H-atom parameters constrained

  • [Delta][rho]max = 0.23 e Å-3

  • [Delta][rho]min = -0.20 e Å-3

Table 1
Hydrogen-bond geometry (Å, °)

D-H...A D-H H...A D...A D-H...A
C3-H3A...O1i 0.93 2.35 3.2646 (18) 168
Symmetry code: (i) [-x, y+{\script{1\over 2}}, -z+{\script{1\over 2}}].

Data collection: APEX2 (Bruker, 2009[Bruker (2009). APEX2, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.]); cell refinement: SAINT (Bruker, 2009[Bruker (2009). APEX2, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.]); data reduction: SAINT; program(s) used to solve structure: SHELXTL (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL 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: IS2763 ).


Acknowledgements

NM gratefully acknowledges funding from the Malaysian Ministry of Science, Technology and Innovation, through the Malaysian Institute of Pharmaceutical and Nutraceutical R&D Initiative Grant (grant Nos. 09-05-IFN-MEB 004 and 304/PFARMASI/650512/I121). HKF and MH thank the Malaysian Government and USM for the Research University Grant (No. 1001/PFIZIK/811160). MH also thanks USM for a post-doctoral research fellowship.

References

Bruker (2009). APEX2, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.
Cremer, D. & Pople, J. A. (1975). J. Am. Chem. Soc. 97, 1354-1358.  [CrossRef] [ChemPort] [ISI]
El Hadri, A., Maldivi, P., Leclerc, G. & Rocher, J.-P. (1995). Bioorg. Med. Chem. 3, 1183-1201.  [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]
Waelbroeck, M., Camus, J., Tastenoy, M. & Christophe, J. (1992). Br. J. Pharmacol. 105, 97-102.  [PubMed] [ChemPort] [ISI]


Acta Cryst (2011). E67, o2409  [ doi:10.1107/S1600536811033848 ]

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