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Synthesis and structural characterization of 3-[1-[4-(2-methylpropyl)phenyl]ethyl]-6-(4-fluorophenyl)-1,2,4-triazolo[3,4-b]-1,3,4-thiadiazole

Published online by Cambridge University Press:  02 September 2019

Gülsüm Gündoğdu Open the ORCID record for Gülsüm Gündoğdu [Opens in a new window] ,
Arzu Karayel ,
Sevim Peri Aytaç ,
Birsen Tozkoparan  and
Filiz Betül Kaynak
Gülsüm Gündoğdu*
Affiliation:
Faculty of Engineering, Department of Physics Engineering, Hacettepe University, 06800 Beytepe, Ankara, Turkey
Arzu Karayel
Affiliation:
Faculty of Arts and Sciences, Department of Physics, Hitit University, 19030 Çorum, Turkey
Sevim Peri Aytaç
Affiliation:
Faculty of Pharmacy, Department of Pharmaceutical Chemistry, Hacettepe University, 06100 Sıhhiye, Ankara, Turkey
Birsen Tozkoparan
Affiliation:
Faculty of Pharmacy, Department of Pharmaceutical Chemistry, Hacettepe University, 06100 Sıhhiye, Ankara, Turkey
Filiz Betül Kaynak
Affiliation:
Faculty of Engineering, Department of Physics Engineering, Hacettepe University, 06800 Beytepe, Ankara, Turkey
*
a)Author to whom correspondence should be addressed. Electronic mail: gulsum.gnd@hacettepe.edu.tr
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Abstract

3-[1-[4-(2-Methylpropyl)phenyl]ethyl]-6-(4-fluorophenyl)-1,2,4-triazolo[3,4-b]-1,3,4-thiadiazole (C21H21FN4S) has been synthesized as a member of a series of triazolothiadiazoles having NSAIDs moieties with cytotoxic activity. The crystal structure of this new compound has been solved and refined using conventional laboratory X-ray powder diffraction data and optimized using density functional techniques. The final structure solution was achieved by Rietveld refinement using soft restraints on all non-H atom bond lengths and angles. This compound crystallizes in $P\bar{1}\;$ space group, with the unit cell parameters a = 5.5880(4) Å, b = 9.3074(7) Å, c = 19.497(4) Å, α = 99.311(10)°, β = 91.925(9)°, γ = 98.199(6)°, and V = 988.8(2) Å3. To complement and verify the structure solution of the compound, the density functional theory (DFT) calculations were performed by using the local density approximation and the generalized gradient approximation for exchange-correlation energy. In order to see the effect of the van der Waals interactions on the electronic structure, the relevant structure was also optimized with B3LYP-D2, PBE-D2, and optB88-vdW functionals. The refined crystal structure was confirmed by the DFT calculations. The best agreement with the experimental structure was achieved by optB88-vdW functional.

Keywords

1,2,4-triazolo[3,4-b]-1,3,4-thiadiazole derivativeslaboratory X-ray powder diffractionRietveld refinementcrystal structureDFT
Type
Technical Article
Information
Powder Diffraction , Volume 34 , Issue 4 , December 2019 , pp. 325 - 330
Copyright
Copyright © International Centre for Diffraction Data 2019 

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Footnotes

*

This article is a part of the PhD thesis of Gülsüm Gündoğdu.

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