The crystals of C5H8N4OS are orthorhombic, space group P212121 (Z=4),a=5.601(1),b=10.224(3), andc=12.233(2) Å. 1,2,4-Triazole ring is approximately planar while 1,3-thiazine ring adopts a C(5)-sofa conformation flattened at the N−C−S end with axial hydroxy group at the opposite side of the ring. The three intermolecular hydrogen bonds, N(3)...O(8), N(3)...N(2), and O(8)...N(1) form a three-dimensional hydrogen bonds network in the crystal. The structure is the first 5H-1,2,4-triazolo [3,4-b] 1,3-thiazine reported in the literature. It shows less aromatic character and smaller delocalization of π electrons of the triazole ring than those in known analogs with [5,1-b] junction.
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Foks, H., Rudnicka, W., Głowka, M. L., Kaliszan, R., Nasal, A., Damasiewicz, B., Radwańska, A., Petrusewicz, J., Trzeciak, H., Okopień, B., Janowiec, M., and Zwolska-Kwiek, Z. (1992)Pharmazie 47, 770–773.
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Główka, M.L. Crystal structure of enantiomeric 3-amino-6,7-dihydro-6-hydroxy-5H-1,2,4-triazolo [3,4-b] 1,3-thiazine. J Chem Crystallogr 24, 273–276 (1994). https://doi.org/10.1007/BF01670356
- Physical Chemistry
- Crystal Structure
- Hydrogen Bond
- Inorganic Chemistry