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|Title:||Favipiravir: Insight into the Crystal Structure, Hirshfeld Surface Analysis and Computational Study|
|Authors:||Babashkina, M. G.|
Kertman, A. V.
Safin, D. A.
|Publisher:||Springer Science and Business Media Deutschland GmbH|
Springer Science and Business Media LLC
|Citation:||Favipiravir: Insight into the Crystal Structure, Hirshfeld Surface Analysis and Computational Study / M. G. Babashkina, A. Frontera, A. V. Kertman et al. — DOI 10.30759/1728-9718-2021-3(72)-169-179 // Journal of the Iranian Chemical Society. — 2022. — Vol. 19. — Iss. 1. — P. 85-94.|
|Abstract:||In this work we report structural and computational studies of favipiravir, which is now used as a drug for COVID-19 treatment. The molecule is completely flat and stabilized by an intramolecular O–H···O hydrogen bond, yielding a six-membered pseudo-aromatic ring. The aromaticity index of this pseudo-aromatic ring was found to be 0.748, while the same indix for the pyrazine ring in favipiravir was found to be 0.954. The crystal packing of favipiravir is mainly constructed through intermolecular N–H···O, N–H···N and C–H···O hydrogen bonds, yielding a 3D supramolecular framework with a zst topology defined by the point symbol of (65·8). The crystal structure of favipiravir is further stabilized by weak C–F···F–C intermolecular type II dihalogen interactions, yielding a 1D supramolecular polymeric chain. More than 80% of the total Hirshfeld surface area for favipiravir is occupied by H···H/C/N/O/F and C···N/O contacts. Energy frameworks have been calculated to additionally analyze the overall crystal packing. It was established that the structure of favipiravir is mainly characterized by the dispersion energy framework followed by the less significant electrostatic energy framework contribution. Finally, by using density functional theory (DFT) calculations and the quantum theory of atoms in molecules, we have assigned the interaction energy of each hydrogen bond, which can be helpful to develop scoring functions to be used in force fields/docking calculations. © 2021, Iranian Chemical Society.|
HIRSHFELD SURFACE ANALYSIS
|metadata.dc.description.sponsorship:||A. Frontera thanks the MICIU/AEI of Spain (project CTQ2017-85821-R FEDER funds) for financial support.|
|Appears in Collections:||Научные публикации, проиндексированные в SCOPUS и WoS CC|
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