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Volume 69 
Part 9 
Page o1424  
September 2013  

Received 24 July 2013
Accepted 8 August 2013
Online 14 August 2013

Key indicators
Single-crystal X-ray study
T = 293 K
Mean [sigma](C-C) = 0.003 Å
R = 0.046
wR = 0.131
Data-to-parameter ratio = 17.4
Details
Open access

2-Chloro-1-(3,3-dimethyl-2,6-diphenylpiperidin-1-yl)ethanone

aPG and Research Department of Physics, Queen Mary's College, Chennai-4, Tamilnadu, India, and bDepartment of Chemistry, Government Arts College (Autonomous), Coimbatore 641 018, Tamilnadu, India
Correspondence e-mail: guqmc@yahoo.com

In the title compound, C21H24ClNO, the piperidine ring adopts a chair conformation. The two phenyl rings are inclined to one another by 20.7 (1)°, and are inclined to the mean plane of the four planar atoms of the piperidine ring by 87.64 (10) and 70.8 (1)°. The molecular structure features short intramolecular C-H...Cl and C-H...O contacts. In the crystal, there are no significant intermolecular interactions present.

Related literature

For the synthesis of the title compound, see: Venkatraj et al. (2008[Venkatraj, M., Ponnuswamy, S. & Jeyaraman, R. (2008). Indian J. Chem. Sect. B, 47, 411-426.]). For the biological activity of piperdine derivatives, see: Ramalingan et al. (2004[Ramalingan, C., Balasubramanian, S., Kabilan, S. & Vasudevan, M. (2004). Eur. J. Med. Chem. 39, 527-533.]), Weintraub et al. (2003[Weintraub, P. M., Sabol, J. S., Kane, J. M. & Borcherding, D. R. (2003). Tetrahedron, 59, 2953-2989.]); Ramachandran et al. (2011[Ramachandran, R., Rani, M., Senthan, S., Jeong, Y. T. & Kabilan, S. (2011). Eur. J. Med. Chem. 46, 1926-1934.]). For a related structure, see: Aridoss et al. (2011[Aridoss, G., Sundaramoorthy, S., Velmurugan, D. & Jeong, Y. T. (2011). Acta Cryst. E67, o540.]). 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
  • C21H24ClNO

  • Mr = 341.86

  • Triclinic, [P \overline 1]

  • a = 7.5488 (6) Å

  • b = 9.9706 (7) Å

  • c = 12.9887 (10) Å

  • [alpha] = 106.783 (4)°

  • [beta] = 93.022 (4)°

  • [gamma] = 102.347 (4)°

  • V = 907.45 (12) Å3

  • Z = 2

  • Mo K[alpha] radiation

  • [mu] = 0.22 mm-1

  • T = 293 K

  • 0.22 × 0.20 × 0.20 mm

Data collection
  • Bruker Kappa APEXII CCD diffractometer

  • Absorption correction: multi-scan (SADABS; Bruker, 2004[Bruker (2004). APEX2, SAINT, XPREP and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.]) Tmin = 0.953, Tmax = 0.958

  • 13736 measured reflections

  • 3806 independent reflections

  • 3169 reflections with I > 2[sigma](I)

  • Rint = 0.026

Refinement
  • R[F2 > 2[sigma](F2)] = 0.046

  • wR(F2) = 0.131

  • S = 1.02

  • 3806 reflections

  • 219 parameters

  • H-atom parameters constrained

  • [Delta][rho]max = 0.26 e Å-3

  • [Delta][rho]min = -0.38 e Å-3

Table 1
Hydrogen-bond geometry (Å, °)

D-H...A D-H H...A D...A D-H...A
C7-H7...Cl1 0.98 2.68 3.3736 (16) 128
C13-H13...O1 0.98 2.27 2.732 (2) 108

Data collection: APEX2 (Bruker, 2004[Bruker (2004). APEX2, SAINT, XPREP and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.]); cell refinement: SAINT (Bruker, 2004[Bruker (2004). APEX2, SAINT, XPREP and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.]); data reduction: SAINT and XPREP (Bruker, 2004[Bruker (2004). APEX2, SAINT, XPREP and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.]); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); molecular graphics: ORTEP-3 for Windows (Farrugia, 2012[Farrugia, L. J. (2012). J. Appl. Cryst. 45, 849-854.]); software used to prepare material for publication: SHELXL97 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: SU2628 ).


Acknowledgements

SP and SA thank the UGC, New Delhi, for financial assistance in the form of a Major Research Project. The authors thank Professor D. Velmurugan, Centre for Advanced Study in Crystallography and Biophysics, University of Madras, for providing data collection and computer facilities.

References

Aridoss, G., Sundaramoorthy, S., Velmurugan, D. & Jeong, Y. T. (2011). Acta Cryst. E67, o540.  [CSD] [CrossRef] [details]
Bruker (2004). APEX2, SAINT, XPREP and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.
Cremer, D. & Pople, J. A. (1975). J. Am. Chem. Soc. 97, 1354-1358.  [CrossRef] [ChemPort] [ISI]
Farrugia, L. J. (2012). J. Appl. Cryst. 45, 849-854.  [ISI] [CrossRef] [ChemPort] [details]
Ramachandran, R., Rani, M., Senthan, S., Jeong, Y. T. & Kabilan, S. (2011). Eur. J. Med. Chem. 46, 1926-1934.  [ISI] [CSD] [CrossRef] [ChemPort] [PubMed]
Ramalingan, C., Balasubramanian, S., Kabilan, S. & Vasudevan, M. (2004). Eur. J. Med. Chem. 39, 527-533.  [ISI] [CrossRef] [PubMed] [ChemPort]
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.  [CrossRef] [ChemPort] [details]
Spek, A. L. (2009). Acta Cryst. D65, 148-155.  [ISI] [CrossRef] [ChemPort] [details]
Venkatraj, M., Ponnuswamy, S. & Jeyaraman, R. (2008). Indian J. Chem. Sect. B, 47, 411-426.
Weintraub, P. M., Sabol, J. S., Kane, J. M. & Borcherding, D. R. (2003). Tetrahedron, 59, 2953-2989.  [ISI] [CrossRef] [ChemPort]


Acta Cryst (2013). E69, o1424  [ doi:10.1107/S1600536813022289 ]

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