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Volume 69 
Part 10 
Page o1545  
October 2013  

Received 26 May 2013
Accepted 30 August 2013
Online 18 September 2013

Key indicators
Single-crystal X-ray study
T = 293 K
Mean [sigma](C-C) = 0.003 Å
R = 0.046
wR = 0.139
Data-to-parameter ratio = 17.3
Details
Open access

[(4E)-3-Ethyl-1-methyl-2,6-diphenylpiperidin-4-ylidene]amino 3-methylbenzoate

aCentre of Advanced Study in Crystallography and Biophysics, University of Madras, Maraimalai Campus (Guindy Campus), Chennai 600 025, India, and bDepartment of Chemistry, Annamalai University, Annamalai Nagar, Chidambaram 608 002, India
Correspondence e-mail: shirai2011@gmail.com

In the title compound, C28H30N2O2, the piperidine ring exists in a chair conformation with an equatorial orientation of the phenyl rings and methyl group substituted on the heterocycle. In the crystal, C-H...[pi] interactions result in chains of molecules running parallel to the a-axis direction.

Related literature

For the synthesis and background to the biological activity of piperidinyl-4-one derivatives, see: Parthiban et al. (2009[Parthiban, P., Balasubramanian, S., Aridoss, G. & Kabilan, S. (2009). Bioorg. Med. Chem. Lett. 19, 2981-2985.], 2011[Parthiban, P., Pallela, R., Kim, S. K., Park, D. H. & Jeong, Y. T. (2011). Bioorg. Med. Chem. Lett. 21, 6678-6686.]). For crystal structures of related compounds, see: Park et al. (2012a[Park, D. H., Ramkumar, V. & Parthiban, P. (2012a). Acta Cryst. E68, o524.],b[Park, D. H., Ramkumar, V. & Parthiban, P. (2012b). Acta Cryst. E68, o525.]). For ring puckering parameters, see: Cremer & Pople (1975[Cremer, D. & Pople, J. A. (1975). J. Am. Chem. Soc. 97, 1354-1358.]).

[Scheme 1]

Experimental

Crystal data
  • C28H30N2O2

  • Mr = 426.54

  • Triclinic, [P \overline 1]

  • a = 10.5220 (15) Å

  • b = 11.8295 (16) Å

  • c = 11.987 (3) Å

  • [alpha] = 112.871 (11)°

  • [beta] = 97.939 (11)°

  • [gamma] = 110.123 (8)°

  • V = 1225.5 (4) Å3

  • Z = 2

  • Mo K[alpha] radiation

  • [mu] = 0.07 mm-1

  • T = 293 K

  • 0.20 × 0.20 × 0.20 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 = 0.986, Tmax = 0.986

  • 18615 measured reflections

  • 5042 independent reflections

  • 3610 reflections with I > 2[sigma](I)

  • Rint = 0.023

Refinement
  • R[F2 > 2[sigma](F2)] = 0.046

  • wR(F2) = 0.139

  • S = 1.03

  • 5042 reflections

  • 292 parameters

  • H-atom parameters constrained

  • [Delta][rho]max = 0.15 e Å-3

  • [Delta][rho]min = -0.17 e Å-3

Table 1
Hydrogen-bond geometry (Å, °)

Cg1 is the centroid of the C15-C20 ring.

D-H...A D-H H...A D...A D-H...A
C11-H11...Cg1i 0.93 2.93 3.761 (2) 149
C23-H23...Cg1ii 0.93 2.89 3.730 (3) 151
Symmetry codes: (i) -x+2, -y+1, -z+1; (ii) -x+3, -y+1, -z+1.

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: PV2635 ).


Acknowledgements

The authors thank the TBI X-ray facility, CAS in Crystallography and Biophysics, University of Madras, India, for the data collection·TV, TS and DV thank the UGC (SAP-CAS) for providing facilities to the department.

References

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]
Park, D. H., Ramkumar, V. & Parthiban, P. (2012a). Acta Cryst. E68, o524.  [CSD] [CrossRef] [IUCr Journals]
Park, D. H., Ramkumar, V. & Parthiban, P. (2012b). Acta Cryst. E68, o525.  [CSD] [CrossRef] [IUCr Journals]
Parthiban, P., Balasubramanian, S., Aridoss, G. & Kabilan, S. (2009). Bioorg. Med. Chem. Lett. 19, 2981-2985.  [CSD] [CrossRef] [PubMed] [ChemPort]
Parthiban, P., Pallela, R., Kim, S. K., Park, D. H. & Jeong, Y. T. (2011). Bioorg. Med. Chem. Lett. 21, 6678-6686.  [CrossRef] [ChemPort] [PubMed]
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, o1545  [ doi:10.1107/S1600536813024276 ]

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