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Volume 69 
Part 8 
Page o1348  
August 2013  

Received 1 July 2013
Accepted 15 July 2013
Online 27 July 2013

Key indicators
Single-crystal X-ray study
T = 293 K
Mean [sigma](C-C) = 0.004 Å
R = 0.048
wR = 0.136
Data-to-parameter ratio = 18.2
Details
Open access

1-Dichloroacetyl-t-3-isopropyl-r-2,c-6-diphenylpiperidin-4-one

aCentre of Advanced Study in Crystallography and Biophysics, University of Madras, Guindy Campus, Chennai 600 025, India, and bDepartment of Chemistry, Government Arts College (Autonomous), Coimbatore 641 018, India
Correspondence e-mail: mnpsy2004@yahoo.com

In the title compound, C22H23Cl2NO2, the piperidine ring adopts a twist-boat conformation. The phenyl rings substituted at the 2- and 6-positions of the piperidine ring subtend dihedral angles of 60.6 (2) and 84.2 (1)°, respectively, with the mean plane of the piperidine ring. In the crystal, molecules are linked by C-H...O interactions into zigzag chains running along the c-axis direction.

Related literature

For the biological activity of piperidine derivatives, see: Aridoss et al. (2009[Aridoss, G., Parthiban, P., Ramachandran, R., Prakash, M., Kabilan, S. & Jeong, Y. T. (2009). Eur. J. Med. Chem. 44, 577-592.]); Nalanishi et al. (1974[Nalanishi, M., Shiraki, M., Kobayakawa, T. & Kobayashi, R. (1974). Japanese Patent No. 74-3987.]); Michael (2001[Michael, J. P. (2001). The Alkaloids. Chemistry and Biology, edited by G. A. Cordell, Vol. 55, pp. 91-258. New York: Academic Press.]); Pinder (1992[Pinder, A. R. (1992). Nat. Prod. Rep. 9, 491-504.]); Rubiralta et al. (1991[Rubiralta, M., Giralt, E. & Diez, A. (1991). Piperidine: Structure, Preparation, Reactivity, and Synthetic Applications of Piperidine and its Derivatives, pp. 225-312. Amsterdam: Elsevier.]). For puckering parameters, see: Cremer & Pople (1975[Cremer, D. & Pople, J. A. (1975). J. Am. Chem. Soc. 97, 1354-1358.]). For asymmetry parameters, see: Nardelli (1983[Nardelli, M. (1983). Acta Cryst. C39, 1141-1142.]).

[Scheme 1]

Experimental

Crystal data
  • C22H23Cl2NO2

  • Mr = 404.31

  • Orthorhombic, P c a 21

  • a = 18.4336 (14) Å

  • b = 9.4516 (7) Å

  • c = 11.7077 (9) Å

  • V = 2039.8 (3) Å3

  • Z = 4

  • Mo K[alpha] radiation

  • [mu] = 0.34 mm-1

  • T = 293 K

  • 0.22 × 0.20 × 0.18 mm

Data collection
  • Bruker SMART APEXII CCD diffractometer

  • Absorption correction: multi-scan (SADABS; Bruker, 2008[Bruker (2008). APEX2, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.]) Tmin = 0.929, Tmax = 0.941

  • 10509 measured reflections

  • 4437 independent reflections

  • 3882 reflections with I > 2[sigma](I)

  • Rint = 0.022

Refinement
  • R[F2 > 2[sigma](F2)] = 0.048

  • wR(F2) = 0.136

  • S = 1.04

  • 4437 reflections

  • 244 parameters

  • 1 restraint

  • H-atom parameters constrained

  • [Delta][rho]max = 0.69 e Å-3

  • [Delta][rho]min = -0.47 e Å-3

  • Absolute structure: Flack (1983[Flack, H. D. (1983). Acta Cryst. A39, 876-881.]), 1759 Friedel pairs

  • Absolute structure parameter: -0.08 (8)

Table 1
Hydrogen-bond geometry (Å, °)

D-H...A D-H H...A D...A D-H...A
C2-H2...O1i 0.98 2.39 3.144 (3) 133
Symmetry code: (i) [-x+{\script{3\over 2}}, y, z+{\script{1\over 2}}].

Data collection: APEX2 (Bruker, 2008[Bruker (2008). APEX2, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.]); cell refinement: SAINT (Bruker, 2008[Bruker (2008). APEX2, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.]); data reduction: SAINT; 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: BT6918 ).


Acknowledgements

PS thanks the UGC, New Delhi, for financial support in the form of a Research Fellowship in Science for Meritorious Students. SP thanks the UGC, New Delhi, for financial assistance in the form of a Major Research Project.

References

Aridoss, G., Parthiban, P., Ramachandran, R., Prakash, M., Kabilan, S. & Jeong, Y. T. (2009). Eur. J. Med. Chem. 44, 577-592.  [Web of Science] [CrossRef] [PubMed] [ChemPort]
Bruker (2008). 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] [Web of Science]
Farrugia, L. J. (2012). J. Appl. Cryst. 45, 849-854.  [Web of Science] [CrossRef] [ChemPort] [IUCr Journals]
Flack, H. D. (1983). Acta Cryst. A39, 876-881.  [CrossRef] [IUCr Journals]
Michael, J. P. (2001). The Alkaloids. Chemistry and Biology, edited by G. A. Cordell, Vol. 55, pp. 91-258. New York: Academic Press.
Nalanishi, M., Shiraki, M., Kobayakawa, T. & Kobayashi, R. (1974). Japanese Patent No. 74-3987.
Nardelli, M. (1983). Acta Cryst. C39, 1141-1142.  [CrossRef] [IUCr Journals]
Pinder, A. R. (1992). Nat. Prod. Rep. 9, 491-504.  [CrossRef] [ChemPort]
Rubiralta, M., Giralt, E. & Diez, A. (1991). Piperidine: Structure, Preparation, Reactivity, and Synthetic Applications of Piperidine and its Derivatives, pp. 225-312. Amsterdam: Elsevier.
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.  [CrossRef] [ChemPort] [IUCr Journals]
Spek, A. L. (2009). Acta Cryst. D65, 148-155.  [Web of Science] [CrossRef] [ChemPort] [IUCr Journals]


Acta Cryst (2013). E69, o1348  [ doi:10.1107/S1600536813019582 ]

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