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

Al-Dajani, M.T.M.; Adballah, H.H.; Mohamed, N.; Hemamalini, M.; Fun, H.-K.

doi:10.1107/S1600536811033848

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 (C-C) = 0.002 Å
R = 0.045
wR = 0.136
Data-to-parameter ratio = 22.7
Details

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

Mohammad T. M. Al-Dajani,^a Hassan H. Adballah,^b Nornisah Mohamed,^a Madhukar Hemamalini ^c and Hoong-Kun Fun ^c ^*⁺

^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-HO hydrogen bonds, forming a zigzag chain along the b axis.

Related literature

For the biological applications of piperidine derivatives, see: Waelbroeck et al. (1992); El Hadri et al. (1995). For puckering parameters, see: Cremer & Pople (1975).

Experimental

Crystal data

C₁₃H₁₅F₂NO
M_r = 239.26
Monoclinic, P 2₁ /c
a = 9.1807 (7) Å
b = 10.9910 (8) Å
c = 13.2477 (8) Å
= 115.582 (4)°
V = 1205.71 (15) Å³
Z = 4
Mo K radiation
= 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) T_min = 0.956, T_max = 0.981
11030 measured reflections
3513 independent reflections
2617 reflections with I > 2(I)
R_int = 0.018

Refinement

R[F² > 2(F²)] = 0.045
wR(F²) = 0.136
S = 1.06
3513 reflections
155 parameters
H-atom parameters constrained
_max = 0.23 e Å^-3
_min = -0.20 e Å^-3

Table 1
Hydrogen-bond geometry (Å, °)

D-HA	D-H	HA	DA	D-HA
C3-H3AO1ⁱ	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); cell refinement: SAINT (Bruker, 2009); data reduction: SAINT; program(s) used to solve structure: SHELXTL (Sheldrick, 2008); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL and PLATON (Spek, 2009).

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.
El Hadri, A., Maldivi, P., Leclerc, G. & Rocher, J.-P. (1995). Bioorg. Med. Chem. 3, 1183-1201.
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.
Spek, A. L. (2009). Acta Cryst. D65, 148-155.
Waelbroeck, M., Camus, J., Tastenoy, M. & Christophe, J. (1992). Br. J. Pharmacol. 105, 97-102.

organic compounds