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Volume 70 
Part 5 
Page o513  
May 2014  

Received 23 January 2014
Accepted 26 March 2014
Online 2 April 2014

Key indicators
Single-crystal X-ray study
T = 295 K
Mean [sigma](C-C) = 0.003 Å
R = 0.071
wR = 0.214
Data-to-parameter ratio = 70.6
Details
Open access

Methyl ({[(4E)-1,3-dimethyl-2,6-di­phenyl­piperidin-4-yl­idene]amino}­oxy)acetate

aDepartment of Physics, Shri Angalamman College of Engineering and Technology, Siruganoor, Tiruchirappalli, India,bDepartment of Chemistry, Annamalai University, Annamalainagar, Chidambaram, India,cDepartment of Chemistry, Urumu Dhanalakshmi College, Tiruchirappalli 620 019, India, and dDepartment of Physics, Urumu Dhanalakshmi College, Tiruchirappalli 620 019, India
Correspondence e-mail: sakthi2udc@gmail.com

In the title compound, C22H26N2O3, the piperidine ring exhibits a chair conformation. The phenyl rings attached to the piperidine at the 2- and 6-positions have axial orientations. These rings make a dihedral angle of 49.75 (11)°. The amino­oxy acetate group attached at the 4-position has an equatorial orientation. In the crystal, inversion dimers linked by pairs of C-H...[pi] inter­actions occur.

Related literature

For background and the importance of oxime ethers, see: Crichlow et al. (2007[Crichlow, G. V., Cheng, K. F., Dabideen, D., Ochani, M., Aljabari, B., Pavlov, V. A., Miller, E. J., Lolis, E. & Al-Abed, Y. (2007). J.Biol.Chem. 282, 23089-23095.]). For a study of the in vitro anti­proliferative activity of oxyme ether derivatives, see: Parthiban et al. (2011[Parthiban, P., Pallela, R., Kim, S.-K., Park, D.-H. & Jeong, Y.-T. (2011). Bioorg. Med. Chem. Lett. 21, 6678-6686.]). For their effects on the senescence of cut carnation flowers, see: Zeng et al. (2012[Zeng, Z., Jiang, H., Zhang, H. & Jiang, Z. (2012). Res. Chem. Intermed., 38, 463-470.]). For ring conformations, see: Cremer & Pople (1975[Cremer, D. & Pople, J. A. (1975). J. Am. Chem. Soc. 97, 1354-1358.]). For related structures, 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.]).

[Scheme 1]

Experimental

Crystal data
  • C22H26N2O3

  • Mr = 366.45

  • Monoclinic, P 21 /c

  • a = 8.1662 (9) Å

  • b = 15.0229 (16) Å

  • c = 16.2889 (19) Å

  • [beta] = 93.903 (6)°

  • V = 1993.7 (4) Å3

  • Z = 4

  • Mo K[alpha] radiation

  • [mu] = 0.08 mm-1

  • T = 295 K

  • 0.35 × 0.35 × 0.30 mm

Data collection
  • Bruker Kappa APEXII CCD diffractometer

  • Absorption correction: multi-scan (SADABS; Bruker, 2008[Bruker (2008). APEX2, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.]) Tmin = 0.972, Tmax = 0.976

  • 17582 measured reflections

  • 17582 independent reflections

  • 12046 reflections with I > 2[sigma](I)

Refinement
  • R[F2 > 2[sigma](F2)] = 0.071

  • wR(F2) = 0.214

  • S = 1.06

  • 17582 reflections

  • 249 parameters

  • H-atom parameters constrained

  • [Delta][rho]max = 0.31 e Å-3

  • [Delta][rho]min = -0.29 e Å-3

Table 1
Hydrogen-bond geometry (Å, °)

Cg2 is the centroid of the C1-C6 ring.

D-H...A D-H H...A D...A D-H...A
C22-H22B...Cg2i 0.96 2.76 3.525 (3) 138.00
Symmetry code: (i) -x+1, -y+1, -z+1.

Data collection: APEX2 (Bruker, 2008[Bruker (2008). APEX2, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.]); cell refinement: APEX2 and 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: PLATON (Spek, 2009[Spek, A. L. (2009). Acta Cryst. D65, 148-155.]).


Supporting information for this paper is available from the IUCr electronic archives (Reference: RK2422 ).


Acknowledgements

The auther thank Dr Babu Varghese, Senior Scientific Officer, SAIF, IIT Madras, India, for carrying out the data collection.

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]
Crichlow, G. V., Cheng, K. F., Dabideen, D., Ochani, M., Aljabari, B., Pavlov, V. A., Miller, E. J., Lolis, E. & Al-Abed, Y. (2007). J.Biol.Chem. 282, 23089-23095.  [ChemPort]
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., 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]
Zeng, Z., Jiang, H., Zhang, H. & Jiang, Z. (2012). Res. Chem. Intermed., 38, 463-470.  [Web of Science] [CrossRef] [ChemPort]


Acta Cryst (2014). E70, o513  [ doi:10.1107/S1600536814006667 ]

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