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Volume 69 
Part 8 
Page o1276  
August 2013  

Received 16 May 2013
Accepted 9 July 2013
Online 20 July 2013

Key indicators
Single-crystal X-ray study
T = 293 K
Mean [sigma](C-C) = 0.003 Å
R = 0.047
wR = 0.144
Data-to-parameter ratio = 17.3
Details
Open access

[(4E)-1-Methyl-2,6-diphenyl-3-(propan-2-yl)piperidin-4-ylidene]amino 3-methylbenzoate

aCentre of Advanced Study in Crystallography and Biophysics, University of Madras, Maraimalai (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, C29H32N2O2, the piperidine ring exists in a chair conformation (the bond-angle sum at the sp2-hybridized C atom is 359.79°). The phenyl rings and the methyl group substituted on the heterocyclic ring are in equatorial orientations. In the crystal, pairs of C-H...[pi] interactions result in the formation of inversion dimers.

Related literature

For the synthesis and 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 the 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
  • C29H32N2O2

  • Mr = 440.57

  • Triclinic, [P \overline 1]

  • a = 10.7837 (4) Å

  • b = 11.7075 (4) Å

  • c = 12.0586 (4) Å

  • [alpha] = 114.352 (3)°

  • [beta] = 96.245 (2)°

  • [gamma] = 109.530 (5)°

  • V = 1252.07 (10) 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

  • 18725 measured reflections

  • 5163 independent reflections

  • 3847 reflections with I > 2[sigma](I)

  • Rint = 0.028

Refinement
  • R[F2 > 2[sigma](F2)] = 0.047

  • wR(F2) = 0.144

  • S = 1.04

  • 5163 reflections

  • 298 parameters

  • H-atom parameters constrained

  • [Delta][rho]max = 0.19 e Å-3

  • [Delta][rho]min = -0.20 e Å-3

Table 1
Hydrogen-bond geometry (Å, °)

Cg1 is the centroid of the C16-C21 ring.

D-H...A D-H H...A D...A D-H...A
C11-H11...Cg1i 0.93 2.95 3.778 (2) 149
Symmetry code: (i) -x+2, -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: PV2632 ).


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 the departmental facilities.

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, o1276  [ doi:10.1107/S160053681301893X ]

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