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Volume 69 
Part 4 
Page o609  
April 2013  

Received 1 March 2013
Accepted 21 March 2013
Online 28 March 2013

Key indicators
Single-crystal X-ray study
T = 293 K
Mean [sigma](C-C) = 0.003 Å
R = 0.032
wR = 0.088
Data-to-parameter ratio = 18.0
Details
Open access

1-Dichloroacetyl-t-3,t-5-dimethyl-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, C21H21Cl2NO2, the piperidine ring adopts a distorted boat conformation. The phenyl rings substituted at the 2- and 6-positions of the piperidine ring subtend angles of 87.9 (7) and 70.8 (9)°, respectively, with the best plane through the piperidine ring. In the crystal, molecules are connected by C-H...O and C-H...Cl interactions into layers in the ab plane.

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.]); 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.]). For hydrogen-bond motifs, see: Bernstein et al.(1995[Bernstein, J., Davis, R. E., Shimoni, L. & Chang, N.-L. (1995). Angew. Chem. Int. Ed. Engl. 34, 1555-1573.]).

[Scheme 1]

Experimental

Crystal data
  • C21H21Cl2NO2

  • Mr = 390.29

  • Monoclinic, P 21

  • a = 8.278 (2) Å

  • b = 9.714 (3) Å

  • c = 11.847 (3) Å

  • [beta] = 90.578 (9)°

  • V = 952.5 (5) Å3

  • Z = 2

  • Mo K[alpha] radiation

  • [mu] = 0.36 mm-1

  • T = 293 K

  • 0.20 × 0.18 × 0.17 mm

Data collection
  • Bruker SMART APEXII CCD diffractometer

  • Absorption correction: multi-scan (SADABS; Bruker, 2008[Bruker (2008). APEX2, SADABS and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.]) Tmin = 0.931, Tmax = 0.944

  • 8874 measured reflections

  • 4241 independent reflections

  • 3962 reflections with I > 2[sigma](I)

  • Rint = 0.025

Refinement
  • R[F2 > 2[sigma](F2)] = 0.032

  • wR(F2) = 0.088

  • S = 1.03

  • 4241 reflections

  • 235 parameters

  • 1 restraint

  • H-atom parameters constrained

  • [Delta][rho]max = 0.31 e Å-3

  • [Delta][rho]min = -0.31 e Å-3

  • Absolute structure: Flack (1983[Flack, H. D. (1983). Acta Cryst. A39, 876-881.]), 1745 Friedel pairs

  • Flack parameter: 0.01 (5)

Table 1
Hydrogen-bond geometry (Å, °)

D-H...A D-H H...A D...A D-H...A
C2-H2...O1i 0.98 2.45 3.379 (2) 159
C20-H20...O1i 0.98 2.53 3.273 (2) 132
C21-H21C...Cl1ii 0.96 2.81 3.702 (2) 155
Symmetry codes: (i) [-x+1, y-{\script{1\over 2}}, -z]; (ii) [-x+1, y+{\script{1\over 2}}, -z].

Data collection: APEX2 (Bruker, 2008[Bruker (2008). APEX2, SADABS and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.]); cell refinement: SAINT (Bruker, 2008[Bruker (2008). APEX2, SADABS and SAINT. 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: BT6893 ).


Acknowledgements

PS thanks the UGC, New Delhi, for financial support in the form of a Research Fellowship in Science for Meritorious Students. SP thanks 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.  [ISI] [CrossRef] [PubMed] [ChemPort]
Bernstein, J., Davis, R. E., Shimoni, L. & Chang, N.-L. (1995). Angew. Chem. Int. Ed. Engl. 34, 1555-1573.  [CrossRef] [ChemPort] [ISI]
Bruker (2008). APEX2, SADABS and SAINT. 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]
Flack, H. D. (1983). Acta Cryst. A39, 876-881.  [CrossRef] [details]
Michael, J. P. (2001). The Alkaloids. Chemistry and Biology, edited by G. A. Cordell, Vol. 55, pp. 91-258. New York: Academic Press.
Nardelli, M. (1983). Acta Cryst. C39, 1141-1142.  [CrossRef] [details]
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] [details]
Spek, A. L. (2009). Acta Cryst. D65, 148-155.  [ISI] [CrossRef] [details]


Acta Cryst (2013). E69, o609  [ doi:10.1107/S1600536813007927 ]

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