Journal of Chemical Crystallography

, Volume 41, Issue 6, pp 868–873

Synthesis and Crystal Structure of (2S,6R) Ethyl 1,2,6-triphenyl-4-(phenylamino)-1,2,5,6-tetrahydropyridine-3-carboxylate

  • Ambika Sambyal
  • R. K. Bamezai
  • T. K. Razdan
  • Vivek K. Gupta
Original Paper

DOI: 10.1007/s10870-011-0015-9

Cite this article as:
Sambyal, A., Bamezai, R.K., Razdan, T.K. et al. J Chem Crystallogr (2011) 41: 868. doi:10.1007/s10870-011-0015-9

Abstract

The title compound, (2S,6R), Ethyl 1,2,6-triphenyl-4-(phenylamino)-1,2,5,6-tetrahydropyridine-3-carboxylate (C32H30N2O2), was synthesised by the reaction of benzaldehyde, aniline and ethylacetoacetate, in the presence of l (−) proline–Fe(III) complex, formed in situ, at room temperature. The compound was characterized by spectral methods and X-ray diffraction studies. The compound crystallizes in the triclinic space group P − 1 with the following unit-cell parameters: a = 9.651(4), b = 10.909(5), c = 13.737(7) Å, α = 106.597(7), β = 108.664(8), γ = 99.779(6)°, Z = 2. The crystal structure was solved by direct methods using single-crystal X-ray diffraction data collected at 100 K and refined by full-matrix least-squares procedures to a final R-value of 0.0633 for 3415 observed reflections. The 1,2,5,6-tetrahydropyridine ring exhibits a flat boat conformation. The structure has intra- and intermolecular hydrogen bonds of the type N–H···O, C–H···O and C–H···π, which help to stabilize the crystal structure.

Graphical Abstract

Crystal structure analysis of (2S,6R) Ethyl 1,2,6-triphenyl-4-(phenylamino)-1,2,5,6-tetrahydropyridine-3-carboxylate.
https://static-content.springer.com/image/art%3A10.1007%2Fs10870-011-0015-9/MediaObjects/10870_2011_15_Figa_HTML.gif

Keywords

Asymmetric synthesisCrystal structureDirect methodsHydrogen bondingC–H···π stacking interactionsChiral tetrahydropyridine

Copyright information

© Springer Science+Business Media, LLC 2011

Authors and Affiliations

  • Ambika Sambyal
    • 1
  • R. K. Bamezai
    • 1
  • T. K. Razdan
    • 1
  • Vivek K. Gupta
    • 2
  1. 1.Department of ChemistryUniversity of JammuJammu TawiIndia
  2. 2.Department of PhysicsUniversity of JammuJammu TawiIndia