Journal of Chemical Crystallography

, Volume 44, Issue 1, pp 1–5 | Cite as

Isolation, Characterization and X-ray Structure Determination of 2,5-Bis(4-methylbenzylthio)-1,3,4-thiadiazole

  • Shahedeh Tayamon
  • Edward R. T. Tiekink
  • Farzad Nikpour
  • Thahira Begum S. A. Ravoof
  • Mohamad Ibrahim Mohamed Tahir
  • Karen A. Crouse
Original Paper


The reaction of hydrazine hydrate with carbon disulfide and 4-methylbenzyl chloride in basic solution yielded 2,5-bis(4-methylbenzylthio)-1,3,4-thiadiazole (C18H18N2S3, compound 1) in addition to the expected S-4-methylbenzyldithiocarbazate. The molecule has approximate twofold symmetry with the C=S bond lying on the pseudo axis. The five membered ring is planar with the three S atoms mutually syn, and with pendent 4-methylbenzylthio substituents; the dihedral angle between the terminal rings is 52.21(7)°. The compound 1 crystallizes in the triclinic space group \(P\bar{1}\) with a = 6.0139(3) Å, b = 11.8694(7) Å, c = 12.6330(7) Å, α = 72.583(5)°, β = 82.827(4)°, γ = 89.882(4)° and Z = 2.

Graphical Abstract

In situ cyclization of an authenticated dithiocarbazate gave rise to a supramolecular layerered assembly of new molecules containing a 1,3,4-thiadiazole ring system having a strictly planar central core with mutually syn sulfur atoms and terminal aryl groups twisted out of this plane.


Dithiocarbazate 1,3,4-Thiadiazole Supramolecular structure Crystal structure 



The authors gratefully acknowledge University Putra Malaysia (UPM) for supporting this project under their Research University Grant Scheme (RUGS No. 05–01–11–1243RU) and the Malaysian Fundamental Research Grant Scheme (FRGS No. 01–13–11– 986FR). ST also thanks Siti Khadijah Densabali for collecting the X-ray data. Support from the Ministry of Higher Education, Malaysia, High-Impact Research scheme (UM.C/HIR-MOHE/SC/03) is also gratefully acknowledged.


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Copyright information

© Springer Science+Business Media New York 2013

Authors and Affiliations

  • Shahedeh Tayamon
    • 1
  • Edward R. T. Tiekink
    • 2
  • Farzad Nikpour
    • 3
  • Thahira Begum S. A. Ravoof
    • 1
  • Mohamad Ibrahim Mohamed Tahir
    • 1
  • Karen A. Crouse
    • 1
  1. 1.Department of Chemistry, Faculty of ScienceUniversiti Putra MalaysiaSerdangMalaysia
  2. 2.Department of ChemistryUniversity of MalayaKuala LumpurMalaysia
  3. 3.Department of ChemistryUniversity of KurdistanSanandajIran

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