(IUCr) 1-Chloroacetyl-2,6-bis(3-fluorophenyl)piperidin-4-one

Volume 65
Part 8
Pages o1994-o1995
August 2009

Received 13 July 2009
Accepted 20 July 2009
Online 25 July 2009

Key indicators
Single-crystal X-ray study
T = 293 K
Mean (C-C) = 0.002 Å
R = 0.039
wR = 0.111
Data-to-parameter ratio = 17.1
Details

1-Chloroacetyl-2,6-bis(3-fluorophenyl)piperidin-4-one

G. Aridoss,^a D. Gayathri,^b ⁺ D. Velmurugan,^b M. S. Kim ^a and Yeon Tae Jeong ^a ^*

^aDivision of Image Science and Information Engineering, Pukyong National University, Busan 608-739, Republic of Korea, and ^bCentre of Advanced Study in Crystallography and Biophysics, University of Madras, Guindy Campus, Chennai 600 025, India
Correspondence e-mail: ytjeong@pknu.ac.kr

In the title compound C₁₉H₁₆ClF₂NO₂, the piperidone ring adopts a twist-boat conformation with the two out-of-plane atoms deviating by 0.544 (1) and 0.511 (1) Å from the plane through the remaining atoms in the ring. Sterically favoured non-H-atom CO intermolecular contacts are observed in the structure, within a 3.00 Å range. The crystal packing is stabilized by C-HO and C-HF hydrogen bonds and an intermolecular [pi] - [pi] interaction [centroid-centroid separation of 3.783 (1) Å]. Alternating C-HO and C-HF intermolecular interactions generate chains running along the a axis, while a centrosymmetric R₂²(16) ring involving C-HO interactions is formed centred at (1/2, 1/2, 0).

Related literature

For background to the biological activity of piperidines and piperidones and their derivatives, see: Richardo et al. (1979); Schneider (1996); Mukhtar & Wright (2005); Fleet et al. (1990); Winkler & Holan (1989); Aridoss et al. (2007a, 2008, 2009a). For related structures, see: Gayathri et al. (2008); Ramachandran et al. (2008); Aridoss et al. (2009b). For the synthesis and stereochemistry, see: Krishnapillay et al. (2000); Aridoss et al. (2007b). For ring conformational analysis, see: Cremer & Pople (1975); Nardelli (1983).

Experimental

Crystal data

C₁₉H₁₆ClF₂NO₂
M_r = 363.78
Monoclinic, P 2₁ /n
a = 10.7026 (8) Å
b = 8.2017 (6) Å
c = 19.0447 (15) Å
= 100.629 (1)°
V = 1643.1 (2) Å³
Z = 4
Mo K radiation
= 0.27 mm^-1
T = 293 K
0.29 × 0.25 × 0.22 mm

Data collection

Bruker SMART APEX diffractometer
Absorption correction: none
18143 measured reflections
3875 independent reflections
3515 reflections with I > 2(I)
R_int = 0.018

Refinement

R[F² > 2(F²)] = 0.039
wR(F²) = 0.111
S = 1.03
3875 reflections
226 parameters
H-atom parameters constrained
_max = 0.34 e Å^-3
_min = -0.35 e Å^-3

Table 1
Hydrogen-bond geometry (Å, °)

D-HA	D-H	HA	DA	D-HA
C2-H2BO1ⁱ	0.97	2.60	3.415 (2)	142
C7-H7AF2ⁱⁱ	0.97	2.49	3.270 (2)	137
C18-H18O2ⁱⁱⁱ	0.93	2.55	3.308 (2)	139
Symmetry codes: (i) $[-x+{\script{1\over 2}}, y-{\script{1\over 2}}, -z+{\script{1\over 2}}]$ ; (ii) $[-x+{\script{3\over 2}}, y-{\script{1\over 2}}, -z+{\script{1\over 2}}]$ ; (iii) -x+1, -y+1, -z.

Data collection: SMART (Bruker, 2001); cell refinement: SAINT (Bruker, 2001); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: PLATON (Spek, 2009); software used to prepare material for publication: SHELXL97 and PARST (Nardelli, 1995).

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: BG2281 ).

Acknowledgements

The authors thank Dr K. Ravikumar, Indian Institute of Chemical Technology, Hyderabad, India, for providing the X-ray data collection facility. GA and YTJ are grateful for the support provided by the second stage of the BK21 program, Republic of Korea. Financial support from the University Grants Commission (UGC-SAP) and the Department of Science & Technology (DST-FIST), Government of India, are acknowledged by DV for providing facilities to the department.

References

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Aridoss, G., Balasubramanian, S., Parthiban, P. & Kabilan, S. (2007b). Spectrochim. Acta Part A, 68, 1153-1163.
Aridoss, G., Balasubramanian, S., Parthiban, P., Ramachandran, R. & Kabilan, S. (2007a). Med. Chem. Res. 16, 188-204.
Aridoss, G., Gayathri, D., Velmurugan, D., Kim, M. S. & Jeong, Y. T. (2009b). Acta Cryst. E65, o1708-o1709.
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Richardo, G. J., Juan, B. C., Mario, R. A., Roldan, M. & Peinado, C. R. (1979). Fernando Spen. 47, 168-172.
Schneider, M. J. (1996). In Alkaloids: Chemical and Biological Perspectives, Vol. 10, edited by S. W. Pelletier, pp. 155-157. Oxford: Pergamon.
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organic compounds