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Volume 69 
Part 9 
Page o1371  
September 2013  

Received 1 July 2013
Accepted 23 July 2013
Online 3 August 2013

Key indicators
Single-crystal X-ray study
T = 293 K
Mean [sigma](C-C) = 0.002 Å
R = 0.043
wR = 0.125
Data-to-parameter ratio = 16.8
Details
Open access

r-2,c-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, C17H19N, the piperidine ring adopts a chair conformation. The phenyl rings substituted at the 2- and 6-positions of the piperidine ring subtend dihedral angles of 81.04 (7) and 81.10 (7)° with the best plane of the piperidine ring. The crystal packing features C-H...[pi] interactions.

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.]); Boehringer & Söhne GmbH (1961[Boehringer & Söhne GmbH (1961). Chem. Abstr. 55, 24796g.]); Jain et al. (2005[Jain, R., Chen, D., White, R. J., Patel, D. V. & Yuan, Z. (2005). Curr. Med. Chem. 12, 1607-1627.]); Kubota et al. (1998[Kubota, H., Fujii, M., Ikeda, K., Takeuchi, M., Shibanuma, T. & Isomura, Y. (1998). Chem. Pharm. Bull. 46, 351-354.]); Mobio et al. (1989[Mobio, I. G., Soldatenkov, A. T., Federov, V. O., Ageev, E. A., Sargeeva, N. D., Lin, S., Stashenko, E. E., Prostakov, N. S. & Andreeva, E. I. (1989). Khim. Farm. Zh. 23, 421-427.]); 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 the synthesis of the title compound, 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.]). For asymmetry parameters, see: Nardelli (1983[Nardelli, M. (1983). Acta Cryst. C39, 1141-1142.]).

[Scheme 1]

Experimental

Crystal data
  • C17H19N

  • Mr = 237.33

  • Triclinic, [P \overline 1]

  • a = 5.6450 (9) Å

  • b = 11.2255 (17) Å

  • c = 11.5281 (17) Å

  • [alpha] = 73.911 (9)°

  • [beta] = 89.898 (9)°

  • [gamma] = 81.466 (9)°

  • V = 693.53 (18) Å3

  • Z = 2

  • Mo K[alpha] radiation

  • [mu] = 0.07 mm-1

  • T = 293 K

  • 0.21 × 0.19 × 0.18 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 = 0.986, Tmax = 0.988

  • 9781 measured reflections

  • 2813 independent reflections

  • 2113 reflections with I > 2[sigma](I)

  • Rint = 0.032

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

  • wR(F2) = 0.125

  • S = 1.06

  • 2813 reflections

  • 167 parameters

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

  • [Delta][rho]max = 0.11 e Å-3

  • [Delta][rho]min = -0.20 e Å-3

Table 1
Hydrogen-bond geometry (Å, °)

Cg1 and Cg2 are the centroids of the C13-C18 and C7-C12 rings, respectively.

D-H...A D-H H...A D...A D-H...A
C3-H3A...Cg1i 0.97 3.00 3.719 (2) 132
C10-H10...Cg1ii 0.93 3.01 3.760 (2) 139
C16-H16...Cg2iii 0.93 3.03 3.799 (2) 141
Symmetry codes: (i) -x+2, -y+1, -z+2; (ii) -x+1, -y+2, -z+1; (iii) x, 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: BT6919 ).


Acknowledgements

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.  [ISI] [CrossRef] [PubMed] [ChemPort]
Boehringer & Söhne GmbH (1961). Chem. Abstr. 55, 24796g.
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]
Jain, R., Chen, D., White, R. J., Patel, D. V. & Yuan, Z. (2005). Curr. Med. Chem. 12, 1607-1627.  [ISI] [CrossRef] [PubMed] [ChemPort]
Kubota, H., Fujii, M., Ikeda, K., Takeuchi, M., Shibanuma, T. & Isomura, Y. (1998). Chem. Pharm. Bull. 46, 351-354.  [CrossRef] [ChemPort] [PubMed]
Mobio, I. G., Soldatenkov, A. T., Federov, V. O., Ageev, E. A., Sargeeva, N. D., Lin, S., Stashenko, E. E., Prostakov, N. S. & Andreeva, E. I. (1989). Khim. Farm. Zh. 23, 421-427.  [ChemPort]
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.
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] [details]
Spek, A. L. (2009). Acta Cryst. D65, 148-155.  [ISI] [CrossRef] [ChemPort] [details]


Acta Cryst (2013). E69, o1371  [ doi:10.1107/S1600536813020382 ]

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