2-Ethyl-1-[5-(4-methylphenyl)pyrazol-3-yl]-3-(thiophene-2-carbonyl)isothiourea: molecular ribbons containing three types of hydrogen-bonded ring

Edison Castro, Henry Insuasty, Braulio Insuasty, Justo Cobo, Christopher Glidewell*

*Corresponding author for this work

Research output: Contribution to journalArticlepeer-review


The title compound, C18H18N4OS2, was prepared by reaction of S,S-diethyl 2-thenoylimidodithiocarbonate with 5-amino-3-(4-methylphenyl)-1H-pyrazole using microwave irradiation under solvent-free conditions. In the molecule, the thiophene unit is disordered over two sets of atomic sites, with occupancies of 0.814 (4) and 0.186 (4), and the bonded distances provide evidence for polarization in the acylthiourea fragment and for aromatic type delocalization in the pyrazole ring. An intramolecular N—H…O hydrogen bond is present, forming an S(6) motif, and molecules are linked by N—H…O and N—H…N hydrogen bonds to form a ribbon in which centrosymmetric R22(4) rings, built from N—H…O hydrogen bonds and flanked by inversion-related pairs of S(6) rings, alternate with centrosymmetric R22(6) rings built from N—H…N hydrogen bonds.

Original languageEnglish
Pages (from-to)1064-1068
Number of pages11
JournalActa Crystallographica Section C: Crystal Structure Communications
Issue number11
Publication statusPublished - Nov 2014


  • Crystal structure
  • Isothiourea
  • Thiophene
  • Pharmacological activity
  • Charge-assisted hydrogen bonding
  • Microwave irradiation
  • Solvent-free conditions
  • Molecular ribbons
  • H-3 receptor antagonists
  • Nitric-oxide synthase
  • System
  • Inhibitors


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