Supramolecular assembly of (Z)-ethyl 2-cyano-3-((4-fluorophenyl)amino) acrylate, crystal structure, Hirshfeld surface analysis and DFT studies

Catiúcia R.M.O. Matos, Letícia S. Vitorino, Pedro H.R. De Oliveira, Maria Cecília B.V. De Souza, Anna C. Cunha, Fernanda Da C.S. Boechat, Jackson A.L.C. Resende, José Walkimar De M. Carneiro, Célia M. Ronconi

Research output: Contribution to journalArticlepeer-review

Abstract

A mixture of the E and Z isomers of ethyl 2-cyano-3-((4-fluorophenyl)amino) acrylate was synthesized and characterized by elemental analysis, attenuated total reflectance-Fourier transform infrared spectroscopy, 1H and 13C nuclear magnetic resonance spectroscopy. The structure of the Z isomer was determined by single crystal X-ray diffraction, which revealed a three-dimensional supramolecular network governed by C-H...N, C-H...O, and C-H...F hydrogen bonds and π...π stacking interactions. The combination of these interactions plays an important role in stabilizing the self-assembly process and the molecular conformation. Hirshfeld surface analysis indicated the roles of the noncovalent interactions in the crystal packing, which were quantified by fingerprint plots and DFT calculations.

Original languageEnglish
Pages (from-to)333-340
Number of pages8
JournalJournal of Molecular Structure
Volume1120
DOIs
Publication statusPublished - 15 Sep 2016
Externally publishedYes

Keywords

  • Crystal structure
  • DFT studies
  • Ethyl 2-cyano-3-((4-fluorophenyl)amino) acrylate E and Z isomers
  • Hirshfeld surface analysis
  • Noncovalent interactions

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