Two regioisomers of condensed thio-heterocyclic triazine synthesized from 6-phenyl-3-thioxo-2,3,4,5-tetra-hydro-1,2,4-triazin-5-one

Akiko Hori, Yasuhide Ishida, Takahiro Kikuchi, Kumiko Miyamoto, Hiroshi Sakaguchi

Research output: Contribution to journalArticle

2 Citations (Scopus)

Abstract

In the crystal structure of 6-phenyl-3-thioxo-2,3,4,5-tetra-hydro-1,2,4- triazin-5-one, C 9H 7N 3OS, (I), the 1,2,4-triazine moieties are connected by face-to-face contacts through two kinds of double hydrogen bonds (N - H⋯O and N - H⋯S), which form planar ribbons along the a axis. The ribbons are crosslinked through C - H⋯π interactions between the phenyl rings. The mol-ecular structures of two regioisomeric compounds, namely 6-phenyl-2,3-dihydro-7H-1,3-thia-zolo[3,2-b][1, 2,4]triazin-7-one, C 11H 9N 3OS, (II), and 3-phenyl-6,7-di-hydro-4H-1,3-thia-zolo[2,3-c][1,2,4]triazin-4-one, C 11H 9N 3OS, (III), which were prepared by the condensation reaction of (I) with 1,2-dibromo-ethane, have been characterized by X-ray crystallography and spectroscopic studies. The crystal structures of (II) and (III) both show two crystallographically independent mol-ecules. While the two compounds are isomers, the unit-cell parameters and crystal packing are quite different and (II) has a chiral crystal structure.

Original languageEnglish
JournalActa Crystallographica Section C: Crystal Structure Communications
Volume65
Issue number12
DOIs
Publication statusPublished - 2009
Externally publishedYes

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Triazines
Crystal structure
Ethylene Dibromide
Condensation reactions
X ray crystallography
Isomers
Hydrogen bonds
Crystals

ASJC Scopus subject areas

  • Biochemistry, Genetics and Molecular Biology(all)
  • Medicine(all)

Cite this

Two regioisomers of condensed thio-heterocyclic triazine synthesized from 6-phenyl-3-thioxo-2,3,4,5-tetra-hydro-1,2,4-triazin-5-one. / Hori, Akiko; Ishida, Yasuhide; Kikuchi, Takahiro; Miyamoto, Kumiko; Sakaguchi, Hiroshi.

In: Acta Crystallographica Section C: Crystal Structure Communications, Vol. 65, No. 12, 2009.

Research output: Contribution to journalArticle

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abstract = "In the crystal structure of 6-phenyl-3-thioxo-2,3,4,5-tetra-hydro-1,2,4- triazin-5-one, C 9H 7N 3OS, (I), the 1,2,4-triazine moieties are connected by face-to-face contacts through two kinds of double hydrogen bonds (N - H⋯O and N - H⋯S), which form planar ribbons along the a axis. The ribbons are crosslinked through C - H⋯π interactions between the phenyl rings. The mol-ecular structures of two regioisomeric compounds, namely 6-phenyl-2,3-dihydro-7H-1,3-thia-zolo[3,2-b][1, 2,4]triazin-7-one, C 11H 9N 3OS, (II), and 3-phenyl-6,7-di-hydro-4H-1,3-thia-zolo[2,3-c][1,2,4]triazin-4-one, C 11H 9N 3OS, (III), which were prepared by the condensation reaction of (I) with 1,2-dibromo-ethane, have been characterized by X-ray crystallography and spectroscopic studies. The crystal structures of (II) and (III) both show two crystallographically independent mol-ecules. While the two compounds are isomers, the unit-cell parameters and crystal packing are quite different and (II) has a chiral crystal structure.",
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AU - Miyamoto, Kumiko

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N2 - In the crystal structure of 6-phenyl-3-thioxo-2,3,4,5-tetra-hydro-1,2,4- triazin-5-one, C 9H 7N 3OS, (I), the 1,2,4-triazine moieties are connected by face-to-face contacts through two kinds of double hydrogen bonds (N - H⋯O and N - H⋯S), which form planar ribbons along the a axis. The ribbons are crosslinked through C - H⋯π interactions between the phenyl rings. The mol-ecular structures of two regioisomeric compounds, namely 6-phenyl-2,3-dihydro-7H-1,3-thia-zolo[3,2-b][1, 2,4]triazin-7-one, C 11H 9N 3OS, (II), and 3-phenyl-6,7-di-hydro-4H-1,3-thia-zolo[2,3-c][1,2,4]triazin-4-one, C 11H 9N 3OS, (III), which were prepared by the condensation reaction of (I) with 1,2-dibromo-ethane, have been characterized by X-ray crystallography and spectroscopic studies. The crystal structures of (II) and (III) both show two crystallographically independent mol-ecules. While the two compounds are isomers, the unit-cell parameters and crystal packing are quite different and (II) has a chiral crystal structure.

AB - In the crystal structure of 6-phenyl-3-thioxo-2,3,4,5-tetra-hydro-1,2,4- triazin-5-one, C 9H 7N 3OS, (I), the 1,2,4-triazine moieties are connected by face-to-face contacts through two kinds of double hydrogen bonds (N - H⋯O and N - H⋯S), which form planar ribbons along the a axis. The ribbons are crosslinked through C - H⋯π interactions between the phenyl rings. The mol-ecular structures of two regioisomeric compounds, namely 6-phenyl-2,3-dihydro-7H-1,3-thia-zolo[3,2-b][1, 2,4]triazin-7-one, C 11H 9N 3OS, (II), and 3-phenyl-6,7-di-hydro-4H-1,3-thia-zolo[2,3-c][1,2,4]triazin-4-one, C 11H 9N 3OS, (III), which were prepared by the condensation reaction of (I) with 1,2-dibromo-ethane, have been characterized by X-ray crystallography and spectroscopic studies. The crystal structures of (II) and (III) both show two crystallographically independent mol-ecules. While the two compounds are isomers, the unit-cell parameters and crystal packing are quite different and (II) has a chiral crystal structure.

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