TY - JOUR
T1 - Supramolecular assembly of (Z)-ethyl 2-cyano-3-((4-fluorophenyl)amino) acrylate, crystal structure, Hirshfeld surface analysis and DFT studies
AU - Matos, Catiúcia R.M.O.
AU - Vitorino, Letícia S.
AU - De Oliveira, Pedro H.R.
AU - De Souza, Maria Cecília B.V.
AU - Cunha, Anna C.
AU - Boechat, Fernanda Da C.S.
AU - Resende, Jackson A.L.C.
AU - Carneiro, José Walkimar De M.
AU - Ronconi, Célia M.
N1 - Publisher Copyright:
© 2016 Elsevier B.V.
PY - 2016/9/15
Y1 - 2016/9/15
N2 - 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.
AB - 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.
KW - Crystal structure
KW - DFT studies
KW - Ethyl 2-cyano-3-((4-fluorophenyl)amino) acrylate E and Z isomers
KW - Hirshfeld surface analysis
KW - Noncovalent interactions
UR - http://www.scopus.com/inward/record.url?scp=84974577356&partnerID=8YFLogxK
U2 - 10.1016/j.molstruc.2016.05.033
DO - 10.1016/j.molstruc.2016.05.033
M3 - Article
AN - SCOPUS:84974577356
SN - 0022-2860
VL - 1120
SP - 333
EP - 340
JO - Journal of Molecular Structure
JF - Journal of Molecular Structure
ER -