Trithiacyanuric acid: a second triclinic polymorph

Abstract

The title compound, C3H3N3S3, is a triclinic modification. The other reported modification crystallizes with just one mol­ecule in the asymmetric unit, [Guo et al. (2006 ▶). Cryst. Growth Des. 6, 846–848] and was solved by power X-ray diffraction data. The present modification has Z′ = 2. In the crystal, mol­ecules are linked by strong intra­molecular N—H⋯S hydrogen bonds with set graph-motif R 2 2(8). In both mol­ecules, all of the N atoms and two of the S atoms are involved in hydrogen bonding, with an average H⋯S distance of 2.58 Å and N—H⋯S angles in the range 163–167°. π–π stacking inter­actions are not observed. In the solid state, the mol­ecules exist in the thione form. The mol­ecular and supra­molecular properties are similar in both polymorphs.

Two-Dimensional Networks of Thiocyanuric Acid and Imine Bases Assisted by Weak Hydrogen Bonds

“…This shorter hydrogen bond necessarily brings about closer C–H···S contacts (H···S separation 2.88–2.96 Å) between the coplanar TCA and DPE molecules. A slight lengthening of the C–S bonds is observed for the molecules involved in the TCA dimers, 1.6807(17) Å and 1.6823(17) Å vs. 1.659 Å for the average C–S bond length across the two polymorphs of neutral TCA. , Concomitant shortening of the C–N bonds ortho to the deprotonated nitrogen, both 1.348(2) Å versus 1.366 Å for the average C–N bond length in neutral TCA, is consistent with deprotonated TCA molecules previously described in the literature …”

“…As a result, the structure of 2 forms a three-dimensional structure created by interpenetration of twodimensional sheets. 28 As expected, each N−H 30,31 Concomitant shortening of the C−N bonds ortho to the deprotonated nitrogen, both 1.348(2) Å versus 1.366 Å for the average C−N bond length in neutral TCA, is consistent with deprotonated TCA molecules previously described in the literature. 32 A small degree of undulation of these two-dimensional sheets occurs as a result of a 34.7°angle between the mean planes of adjacent TCA molecules along the (TCA) ∞ chains.…”

Role of Staple Molecules in the Formation of S···S Contact in Thioamides: Experimental Charge Density and Theoretical Studies

“…1 The nondirectional character of the contacts is also supported by the random spread of points in Figure 2d No X 3 synthon has been found for thioamides; however, considering the one longer S•••S contact, this structure can be observed in the structure of trithiocyanuric acid. 9 Very nice examples of S3 synthons are present in structures containing thiocyanate 10,11 and carbon disulfide. 12 To investigate the most representative thioamides of type I, we selected three compounds, namely, 6-aminothiouracil hydrate (ATU•H 2 O) (1), 2-imidazolidinethione (IMT) (2), and 2-thiazolidinethione (TT) (3).…”

“…No X 3 synthon has been found for thioamides; however, considering the one longer S···S contact, this structure can be observed in the structure of trithiocyanuric acid . Very nice examples of S3 synthons are present in structures containing thiocyanate , and carbon disulfide …”

Synthesis, characterization and theoretical calculations of Cu(I) complex of trithiocyanuric acid [Cu(ttc)3]

“…Thus, the availability of multiple σ-donor atoms allows the possibility of forming a variety of polynuclear complexes. Henceforth, the capability of ttc to act as a bridging ligand is used commonly, and it has been observed in several reported polymeric compounds [5][6].…”