r-2,c-6-Bis(4-chloro­phen­yl)-c-3,t-3-dimethyl­piperidin-4-one

Ilango, S.S.; Ponnuswamy, S.; Gayathri, P.; Thiruvalluvar, A.; Butcher, R.J.

doi:10.1107/S1600536808036325

Volume 64
Part 12
Page o2312
December 2008

Received 28 October 2008
Accepted 6 November 2008
Online 13 November 2008

Key indicators
Single-crystal X-ray study
T = 200 K
Mean (C-C) = 0.003 Å
R = 0.039
wR = 0.083
Data-to-parameter ratio = 26.9
Details

r-2,c-6-Bis(4-chlorophenyl)-c-3,t-3-dimethylpiperidin-4-one

S. S. Ilango,^a S. Ponnuswamy,^a P. Gayathri,^b A. Thiruvalluvar ^b ^* and R. J. Butcher ^c

^aDepartment of Chemistry, Government Arts College (Autonomous), Coimbatore 641 018, Tamilnadu, India,^bPG Research Department of Physics, Rajah Serfoji Government College (Autonomous), Thanjavur 613 005, Tamilnadu, India, and ^cDepartment of Chemistry, Howard University, 525 College Street NW, Washington, DC 20059, USA
Correspondence e-mail: athiru@vsnl.net

In the title molecule, C₁₉H₁₉Cl₂NO, the piperidine ring adopts a chair conformation and the dihedral angle between the two benzene rings is 77.23 (7)°. In the crystal structure, molecules are linked by N-HO and C-HO hydrogen bonds, and a weak C-H [pi] interaction is also observed.

Related literature

For a related crystal structure, see: Gayathri et al. (2008). For background on the biological activities of piperidones, see: Dimmock et al. (2001); Perumal et al. (2001). For the synthesis and stereodynamics of piperidin-4-ones and their derivatives, see: Ponnuswamy et al. (2002). For the synthesis, see: Noller & Baliah (1948).

Experimental

Crystal data

C₁₉H₁₉Cl₂NO
M_r = 348.25
Orthorhombic, P n a 2₁
a = 13.1627 (5) Å
b = 22.4739 (7) Å
c = 5.8794 (2) Å
V = 1739.23 (10) Å³
Z = 4
Mo K radiation
= 0.38 mm^-1
T = 200 (2) K
0.44 × 0.31 × 0.22 mm

Data collection

Oxford Diffraction Gemini R diffractometer
Absorption correction: multi-scan (CrysAlis RED; Oxford Diffraction, 2008 $[Oxford Diffraction (2008). CrysAlis CCD and CrysAlis RED. Oxford Diffraction Ltd, Abingdon, Oxfordshire, England.]$ ) T_min = 0.950, T_max = 1.000 (expected range = 0.874-0.920)
19147 measured reflections
5694 independent reflections
2460 reflections with I > 2(I)
R_int = 0.051

Refinement

R[F² > 2(F²)] = 0.039
wR(F²) = 0.083
S = 0.82
5694 reflections
212 parameters
1 restraint
H atoms treated by a mixture of independent and constrained refinement
_max = 0.34 e Å^-3
_min = -0.31 e Å^-3
Absolute structure: Flack (1983), 2278 Friedel pairs
Flack parameter: -0.03 (5)

Table 1
Hydrogen-bond geometry (Å, °)

D-HA	D-H	HA	DA	D-HA
N1-H1O4ⁱ	0.853 (17)	2.312 (17)	3.092 (2)	152.3 (15)
C23-H23O4ⁱⁱ	0.95	2.56	3.377 (2)	144
C31-H31BCg1ⁱⁱⁱ	0.98	2.96	3.7265 (15)	136
Symmetry codes: (i) $[x-{\script{1\over 2}}, -y+{\script{1\over 2}}, z]$ ; (ii) $[x-{\script{1\over 2}}, -y+{\script{1\over 2}}, z-1]$ ; (iii) $[x+{\script{1\over 2}}, -y+{\script{1\over 2}}, z]$ . Cg1 is the centroid of the C61-C66 ring.

Data collection: CrysAlis CCD (Oxford Diffraction, 2008 $[Oxford Diffraction (2008). CrysAlis CCD and CrysAlis RED. Oxford Diffraction Ltd, Abingdon, Oxfordshire, England.]$ ); cell refinement: CrysAlis RED (Oxford Diffraction, 2008 $[Oxford Diffraction (2008). CrysAlis CCD and CrysAlis RED. Oxford Diffraction Ltd, Abingdon, Oxfordshire, England.]$ ); data reduction: CrysAlis RED; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 (Farrugia, 1997); software used to prepare material for publication: PLATON (Spek, 2003).

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: HB2832 ).

Acknowledgements

AT thanks the UGC, India, for the award of a Minor Research Project [File No. MRP-2355/06(UGC-SERO), Link No. 2355, 10/01/2007]. RJB acknowledges the NSF-MRI program for funding the purchase of the X-ray CCD diffractometer.

References

Dimmock, J. R., Padmanilayam, M. P., Puthucode, R. N., Nazarali, A. J., Motaganahalli, N. L., Zello, G. A., Quail, J. W., Oloo, E. O., Kraatz, H. B., Prisciak, J. S., Allen, T. M., Santos, C. L., Balsarini, J., Clercq, E. D. & Manavathu, E. K. (2001). J. Med. Chem. 44, 586-593.
Farrugia, L. J. (1997). J. Appl. Cryst. 30, 565.
Flack, H. D. (1983). Acta Cryst. A39, 876-881.
Gayathri, P., Thiruvalluvar, A., Manimekalai, A., Sivakumar, S. & Butcher, R. J. (2008). Acta Cryst. E64, o1973.
Noller, C. & Baliah, V. (1948). J. Am. Chem. Soc. 70, 3853-3855.
Oxford Diffraction (2008). CrysAlis CCD and CrysAlis RED. Oxford Diffraction Ltd, Abingdon, Oxfordshire, England.
Perumal, R. V., Agiraj, M. & Shanmugapandiyan, P. (2001). Indian Drugs, 38, 156-159.
Ponnuswamy, S., Venkatraj, M., Jeyaraman, R., Suresh Kumar, M., Kumaran, D. & Ponnuswamy, M. N. (2002). Indian J. Chem. Sect B, 41, 614-627.
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.
Spek, A. L. (2003). J. Appl. Cryst. 36, 7-13.

organic compounds