[Journal logo]

Volume 66 
Part 8 
Page o2005  
August 2010  

Received 23 June 2010
Accepted 6 July 2010
Online 14 July 2010

Key indicators
Single-crystal X-ray study
T = 292 K
Mean [sigma](C-C) = 0.003 Å
R = 0.058
wR = 0.193
Data-to-parameter ratio = 19.6
Details
Open access

Ethyl 4-hydroxy-2,6-diphenyl-1-[2-(piperidin-1-yl)acetyl]-1,2,5,6-tetrahydropyridine-3-carboxylate

aDepartment of Image Science and Engineering, Pukyong National University, Busan 608-739, Republic of Korea, and bCentre of Advanced Study in Crystallography and Biophysics, University of Madras, Guindy Campus, Chennai 600 025, India
Correspondence e-mail: ytjeong@pknu.ac.kr

In the title compound, C27H32N2O4, the piperidine and tetrahydropyridine rings adopt chair and half-chair conformations, respectively. The dihedral angle between the two phenyl rings is 32.9 (1)°. The molecular structure is stabilized by a strong intramolecular O-H...O hydrogen bond, generating an S(6) motif. In the crystal, intermolecular C-H...O interactions form a ribbon-like structure along the a axis.

Related literature

For the biological activity of piperidines, see: Aridoss et al. (2008[Aridoss, G., Amirthaganesan, S., Ashok Kumar, N., Kim, J. T., Lim, K. T., Kabilan, S. & Jeong, Y. T. (2008). Bioorg. Med. Chem. Lett. 18, 6542-6548.], 2010[Aridoss, G., Amirthaganesan, S. & Jeong, Y. T. (2010). Bioorg. Med. Chem. Lett. 20, 2242-2249.]). For related structures, see: Subha Nandhini et al. (2003[Subha Nandhini, M., Vijayakumar, V., Mostad, A., Sundaravadivelu, M. & Natarajan, S. (2003). Acta Cryst. E59, o1672-o1674.]); Aridoss et al. (2009a[Aridoss, G., Gayathri, D., Park, K. S., Kim, J. T. & Jeong, Y. T. (2009a). Acta Cryst. E65, o3180-o3181.],b[Aridoss, G., Gayathri, D., Ramachandran, R., Lim, K. T. & Jeong, Y. T. (2009b). Acta Cryst. E65, o3232-o3233.]); Parkin et al. (2004[Parkin, A., Oswald, I. D. H. & Parsons, S. (2004). Acta Cryst. B60, 219-227.]). For ring conformational analysis, see: Cremer & Pople (1975[Cremer, D. & Pople, J. A. (1975). J. Am. Chem. Soc. 97, 1354-1358.]); Nardelli (1983[Nardelli, M. (1983). Acta Cryst. C39, 1141-1142.]).

[Scheme 1]

Experimental

Crystal data
  • C27H32N2O4

  • Mr = 448.55

  • Monoclinic, P 21 /n

  • a = 10.7936 (6) Å

  • b = 9.6752 (6) Å

  • c = 23.2335 (13) Å

  • [beta] = 93.213 (3)°

  • V = 2422.5 (2) Å3

  • Z = 4

  • Mo K[alpha] radiation

  • [mu] = 0.08 mm-1

  • T = 292 K

  • 0.25 × 0.23 × 0.20 mm

Data collection
  • Bruker SMART APEXII area-detector diffractometer

  • Absorption correction: multi-scan (SADABS; Bruker, 2008[Bruker (2008). APEX2, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.]) Tmin = 0.979, Tmax = 0.984

  • 21907 measured reflections

  • 5870 independent reflections

  • 3631 reflections with I > 2[sigma](I)

  • Rint = 0.025

Refinement
  • R[F2 > 2[sigma](F2)] = 0.058

  • wR(F2) = 0.193

  • S = 1.05

  • 5870 reflections

  • 299 parameters

  • 1 restraint

  • H-atom parameters constrained

  • [Delta][rho]max = 0.58 e Å-3

  • [Delta][rho]min = -0.37 e Å-3

Table 1
Hydrogen-bond geometry (Å, °)

D-H...A D-H H...A D...A D-H...A
O2-H2...O3 0.82 1.88 2.598 (3) 145
C2-H2B...O1i 0.97 2.43 3.286 (3) 148
C10-H10...O1ii 0.93 2.50 3.427 (3) 177
Symmetry codes: (i) -x, -y, -z; (ii) -x+1, -y, -z.

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 (Farrugia, 1997[Farrugia, L. J. (1997). J. Appl. Cryst. 30, 565.]); 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: CI5118 ).


Acknowledgements

GA and YTJ are grateful for the support provided by the Corporate-affiliated Research Institute of Academic-Industrial-Institutional Cooperation Improvement Business No. S7080008110. SS and DV thank the TBI X-ray Facility, CAS in Crystallography and Biophysics, University of Madras, India, for the data collection and the University Grants Commission (UGC-SAP) for financial support.

References

Aridoss, G., Amirthaganesan, S., Ashok Kumar, N., Kim, J. T., Lim, K. T., Kabilan, S. & Jeong, Y. T. (2008). Bioorg. Med. Chem. Lett. 18, 6542-6548.  [CSD] [CrossRef] [PubMed] [ChemPort]
Aridoss, G., Amirthaganesan, S. & Jeong, Y. T. (2010). Bioorg. Med. Chem. Lett. 20, 2242-2249.  [CrossRef] [ChemPort] [PubMed]
Aridoss, G., Gayathri, D., Park, K. S., Kim, J. T. & Jeong, Y. T. (2009a). Acta Cryst. E65, o3180-o3181.  [CSD] [CrossRef] [details]
Aridoss, G., Gayathri, D., Ramachandran, R., Lim, K. T. & Jeong, Y. T. (2009b). Acta Cryst. E65, o3232-o3233.  [CSD] [CrossRef] [details]
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] [ISI]
Farrugia, L. J. (1997). J. Appl. Cryst. 30, 565.  [CrossRef] [details]
Nardelli, M. (1983). Acta Cryst. C39, 1141-1142.  [CrossRef] [details]
Parkin, A., Oswald, I. D. H. & Parsons, S. (2004). Acta Cryst. B60, 219-227.
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.  [CrossRef] [details]
Spek, A. L. (2009). Acta Cryst. D65, 148-155.  [ISI] [CrossRef] [details]
Subha Nandhini, M., Vijayakumar, V., Mostad, A., Sundaravadivelu, M. & Natarajan, S. (2003). Acta Cryst. E59, o1672-o1674.  [CSD] [CrossRef] [details]


Acta Cryst (2010). E66, o2005  [ doi:10.1107/S1600536810026619 ]

This is an open-access article distributed under the terms of the Creative Commons Attribution Licence, which permits unrestricted use, distribution, and reproduction in any medium, provided the original authors and source are cited.