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

doi:10.1016/j.molstruc.2016.05.033

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

Universidade Federal do Rio de Janeiro

Research output: Contribution to journal › Article › peer-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 language	English
Pages (from-to)	333-340
Number of pages	8
Journal	Journal of Molecular Structure
Volume	1120
DOIs	https://doi.org/10.1016/j.molstruc.2016.05.033
Publication status	Published - 15 Sep 2016
Externally published	Yes

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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10.1016/j.molstruc.2016.05.033

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Matos, C. R. M. O., Vitorino, L. S., De Oliveira, P. H. R., De Souza, M. C. B. V., Cunha, A. C., Boechat, F. D. C. S., Resende, J. A. L. C., Carneiro, J. W. D. M., & Ronconi, C. M. (2016). Supramolecular assembly of (Z)-ethyl 2-cyano-3-((4-fluorophenyl)amino) acrylate, crystal structure, Hirshfeld surface analysis and DFT studies. Journal of Molecular Structure, 1120, 333-340. https://doi.org/10.1016/j.molstruc.2016.05.033

@article{f7f34681b6c64f3580cd9b315382b41e,

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

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.",

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

author = "Matos, \{Cati{\'u}cia R.M.O.\} and Vitorino, \{Let{\'i}cia S.\} and \{De Oliveira\}, \{Pedro H.R.\} and \{De Souza\}, \{Maria Cec{\'i}lia B.V.\} and Cunha, \{Anna C.\} and Boechat, \{Fernanda Da C.S.\} and Resende, \{Jackson A.L.C.\} and Carneiro, \{Jos{\'e} Walkimar De M.\} and Ronconi, \{C{\'e}lia M.\}",

note = "Publisher Copyright: {\textcopyright} 2016 Elsevier B.V.",

year = "2016",

month = sep,

day = "15",

doi = "10.1016/j.molstruc.2016.05.033",

language = "English",

volume = "1120",

pages = "333--340",

journal = "Journal of Molecular Structure",

issn = "0022-2860",

}

Matos, CRMO, Vitorino, LS, De Oliveira, PHR, De Souza, MCBV, Cunha, AC, Boechat, FDCS, Resende, JALC, Carneiro, JWDM & Ronconi, CM 2016, 'Supramolecular assembly of (Z)-ethyl 2-cyano-3-((4-fluorophenyl)amino) acrylate, crystal structure, Hirshfeld surface analysis and DFT studies', Journal of Molecular Structure, vol. 1120, pp. 333-340. https://doi.org/10.1016/j.molstruc.2016.05.033

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.

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 - https://www.scopus.com/pages/publications/84974577356

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 -

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

Abstract

Keywords

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