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Volume 69 
Part 9 
Page o1441  
September 2013  

Received 11 July 2013
Accepted 1 August 2013
Online 17 August 2013

Key indicators
Single-crystal X-ray study
T = 293 K
Mean [sigma](C-C) = 0.002 Å
R = 0.043
wR = 0.124
Data-to-parameter ratio = 17.6
Details
Open access

3-Ethyl-cis-2,6-diphenylpiperidine

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, C19H23N, the piperidine ring adopts a chair conformation. The phenyl rings at the 2,6-positions of the piperidine ring occupy equatorial orientations. The crystal structure features C-H...[pi] interactions.

Related literature

For the biological activity of piperidine derivatives, see: Nalanishi et al. (1974[Nalanishi, M., Shiraki, M., Kobayakawa, T. & Kobayashi, R. (1974). Jpn Patent 74-3987.]). For the synthesis, see: Ponnuswamy et al. (2002[Ponnuswamy, S., Venkatraj, M., Jeyaraman, R., Suresh Kumar, M., Kumaran, D. & Ponnuswamy, M. N. (2002). Indian J. Chem. Sect. B, 41, 614-627.]). For puckering parameters, see: Cremer & Pople (1975[Cremer, D. & Pople, J. A. (1975). J. Am. Chem. Soc. 97, 1354-1358.]) and for asymmetry parameters, see: Nardelli (1983[Nardelli, M. (1983). Acta Cryst. C39, 1141-1142.]).

[Scheme 1]

Experimental

Crystal data
  • C19H23N

  • Mr = 265.38

  • Triclinic, [P \overline 1]

  • a = 5.5384 (5) Å

  • b = 9.2717 (9) Å

  • c = 16.0483 (14) Å

  • [alpha] = 75.508 (5)°

  • [beta] = 89.474 (5)°

  • [gamma] = 81.625 (5)°

  • V = 789.04 (13) Å3

  • Z = 2

  • Mo K[alpha] radiation

  • [mu] = 0.06 mm-1

  • T = 293 K

  • 0.20 × 0.19 × 0.19 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 = 0.987, Tmax = 0.988

  • 11467 measured reflections

  • 3251 independent reflections

  • 2579 reflections with I > 2[sigma](I)

  • Rint = 0.025

Refinement
  • R[F2 > 2[sigma](F2)] = 0.043

  • wR(F2) = 0.124

  • S = 1.03

  • 3251 reflections

  • 185 parameters

  • H atoms treated by a mixture of independent and constrained refinement

  • [Delta][rho]max = 0.13 e Å-3

  • [Delta][rho]min = -0.18 e Å-3

Table 1
Hydrogen-bond geometry (Å, °)

Cg2 and Cg3 are the centroids of the C7-C12 and C13-C18 rings, respectively.

D-H...A D-H H...A D...A D-H...A
C5-H5B...Cg2i 0.97 3.14 3.893 (2) 136
C10-H10...Cg3ii 0.93 2.92 3.702 (2) 142
C20-H20A...Cg3iii 0.96 3.17 3.926 (2) 137
Symmetry codes: (i) -x+1, -y, -z+1; (ii) -x, -y+1, -z+1; (iii) -x+1, -y+1, -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: NG5337 ).


Acknowledgements

SP thanks the UGC, New Delhi, for financial assistance in the form of a Major Research Project.

References

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]
Nalanishi, M., Shiraki, M., Kobayakawa, T. & Kobayashi, R. (1974). Jpn Patent 74-3987.
Nardelli, M. (1983). Acta Cryst. C39, 1141-1142.  [CrossRef] [details]
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.  [CrossRef] [ChemPort] [details]
Spek, A. L. (2009). Acta Cryst. D65, 148-155.  [ISI] [CrossRef] [ChemPort] [details]


Acta Cryst (2013). E69, o1441  [ doi:10.1107/S1600536813021417 ]

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