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Crystal structure of enantiomeric 3-amino-6,7-dihydro-6-hydroxy-5H-1,2,4-triazolo [3,4-b] 1,3-thiazine

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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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  1. 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.

  2. Główka, M. L., Foks, H., and Rudnicka, W. (1994)J. Cryst. Chem. accepted.

  3. Sheldrick, G. M. (1990)SHELXTL PC version 4.1. An integrated system for solving, refining and displaying crystal structures from diffraction data, Siemens Analytical X-Ray Instruments, Inc. Madison, WI.

  4. Walker, N., and Stuart, D. (1983)Acta Cryst. A39, 158–166.

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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

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  • Hydrogen
  • Physical Chemistry
  • Crystal Structure
  • Hydrogen Bond
  • Inorganic Chemistry