Trithiocyanuric acid: novel cocrystals and analysis of its tautomeric forms

• Published in: Acta crystallographica. Section C, Crystal structure communications Crystal structure communications, 2021-01, Vol.77 (1), p.49-55
• Main Authors: Wzgarda-Raj, Kinga, Rybarczyk-Pirek, Agnieszka Justyna, Wojtulewski, Sławomir, Palusiak, Marcin
• Format: Article
• Language: English
• Subjects: Acids; cocrystal; crystal structure; Crystals; hydrogen bonding; Hydrogen bonds; Quantum chemistry; supramolecular chemistry; tautomerism; trithiocyanuric acid
• ISSN: 2053-2296; 0108-2701; 2053-2296; 1600-5759
• DOI: 10.1107/S2053229620016137

Cocrystals of trithiocyanuric acid with 2,2′‐bipyridyl [1,3,5‐triazinane‐2,4,6‐trithione–2,2′‐bipyridine (2/1), 2C3H3N3S3·C10H8N2, (I)] and 4‐methylbenzohydrazide [1,3,5‐triazinane‐2,4,6‐trithione–4‐methylbenzohydrazide (1/1), C8H10N2O·C3H3N3S3, (II)] crystallize in the monoclinic crystal system. In the crystals, molecules of both components are linked by hydrogen bonds. The trithiocyanuric acid molecules are connected by N—H…S hydrogen bonds forming R22(8) synthons, which are further organized into chain motifs. Computations based on quantum chemistry methods have been performed for a more detailed description of the observed tautomerism of trithiocyanuric acid. The structures of two cocrystals of trithiocyanuric acid with 2,2′‐bipyridyl and 4‐methylbenzohydrazide have been determined. In the crystalline state, the molecular components are linked by N—H…S hydrogen bonds, forming (8) synthons. The observed tautomerism of trithiocyanuric acid was characterized by quantum chemistry methods.