Two N-{[4-(3-aryl-4-sydnonyl­­idene­amino)-5-sulfan­yl­­idene-1H-1,2,4-triazol-3-yl]meth­yl}benzamides as disordered ethanol monosolvates

Chayanna Harish Chinthal, Hemmige S Yathirajan, Anish Kumar Kadambar, Balakrishna Kalluraya, Sabine Foro, Christopher Glidewell

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Two new N-{[4-(3-aryl-4-sydnonyl­idene­amino)-5-sulfanyl­idene-1H-1,2,4-triazol-3-yl]meth­yl}benzamides have been prepared by acid-promoted condensation reactions between 3-aryl-4-formyl­sydnones and N-[(4-amino-5-sulfanyl­idene-1H-1,2,4-triazol-3-yl)meth­yl]benzamide, and both have been crystallized as ethanol monosolvates. N-{[4-(3-Phenyl-4-sydnonyl­idene­amino)-5-sulfanyl­idene-1H-1,2,4-triazol-3-yl]meth­yl}benzamide ethanol monosolvate, C19H15N7O3S·C2H6O (I), and N-({4-[3-(4-methyl­phen­yl)-4-sydnonyl­idene­amino]-5-sulfanyl­idene-1H-1,2,4-triazol-3-yl}meth­yl)benzamide ethanol monosolvate, C20H17N7O3S·C2H6O (II), differ only in the presence of a methyl group for (II) instead of a hydrogen atom for (I), and in both of them the ethanol component is disordered over two sets of atomic sites having occupancies of 0.836 (6) and 0.164 (6) in (I), and 0.906 (6) and 0.094 (6) in (II). Combinations of O—H⋯O and N—H⋯O hydrogen bonds link the mol­ecules into cyclic, centrosymmetric four-mol­ecule aggregates. Comparisons are made with the structures of some related compounds.
Original languageEnglish
Pages (from-to)1057-1061
Number of pages18
JournalActa Crystallographica Section E Crystallographic Communications
Issue numberPart 7
Early online date9 Jun 2020
Publication statusPublished - Jul 2020


  • 1,2,4-triazoles
  • crystal structure
  • Disorder
  • Heterocyclic compounds
  • Hydrogen bonding
  • Supra­molecular assembly
  • Sydnones
  • Synthesis


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