Crystal structure of N-[(2S,5R)-4-oxo-2,3-diphenyl-1,3-thiazinan-5-yl]acetamide 0.375-hydrate

Hemant P. Yennawar, Harnoor Singh, Lee J. Silverberg*, W. T A Harrison (Editor)

*Corresponding author for this work

Research output: Contribution to journalArticle

2 Citations (Scopus)
4 Downloads (Pure)

Abstract

The asymmetric unit of the title compound, C18H18N2O2S.0.375H2O, has two independent organic molecules (A and B) and 3/4 of a water molecule distributed over three sites. In molecule A, the 1, 3-thiazine ring is in a boat conformation, with the C atoms at the 2- and 5-positions out of the plane. The angle between the two phenyl rings is 51.70 (12)°. In molecule B, the thiazine ring is in a half-chair conformation, with the S atom forming the back of the half-chair. The angle between the two phenyl rings is 84.44 (14)°. The A molecule features an intramolecular N - H⋯O hydrogen bond, which closes an S(5) ring motif. In the crystal, the corresponding N - H grouping of the B molecule participates in an intermolecular hydrogen bond to the A molecule. The A molecule participates in a C - H⋯O interaction back to the B molecule, whilst the B molecule features an intramolecular C - H⋯O link, which generates an S(10) loop.

Original languageEnglish
Pages (from-to)62-64
Number of pages3
JournalActa Crystallographica Section E: Structure Reports Online
Volume71
Issue number1
DOIs
Publication statusPublished - 1 Jan 2015

Fingerprint

Hydrates
hydrates
Crystal structure
crystal structure
Molecules
molecules
Thiazines
thiazine (trademark)
rings
seats
Conformations
Hydrogen bonds
diphenyl
acetamide
hydrogen bonds
Atoms
boats
Boats
atoms
Crystals

Keywords

  • 1,3-thiazin-4-one
  • Boat
  • Crystal structure
  • Half-chair
  • Hydrogen bonding
  • Thiazine ring

ASJC Scopus subject areas

  • Condensed Matter Physics
  • Materials Science(all)
  • Chemistry(all)

Cite this

Crystal structure of N-[(2S,5R)-4-oxo-2,3-diphenyl-1,3-thiazinan-5-yl]acetamide 0.375-hydrate. / Yennawar, Hemant P.; Singh, Harnoor; Silverberg, Lee J.; Harrison, W. T A (Editor).

In: Acta Crystallographica Section E: Structure Reports Online, Vol. 71, No. 1, 01.01.2015, p. 62-64.

Research output: Contribution to journalArticle

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abstract = "The asymmetric unit of the title compound, C18H18N2O2S.0.375H2O, has two independent organic molecules (A and B) and 3/4 of a water molecule distributed over three sites. In molecule A, the 1, 3-thiazine ring is in a boat conformation, with the C atoms at the 2- and 5-positions out of the plane. The angle between the two phenyl rings is 51.70 (12)°. In molecule B, the thiazine ring is in a half-chair conformation, with the S atom forming the back of the half-chair. The angle between the two phenyl rings is 84.44 (14)°. The A molecule features an intramolecular N - H⋯O hydrogen bond, which closes an S(5) ring motif. In the crystal, the corresponding N - H grouping of the B molecule participates in an intermolecular hydrogen bond to the A molecule. The A molecule participates in a C - H⋯O interaction back to the B molecule, whilst the B molecule features an intramolecular C - H⋯O link, which generates an S(10) loop.",
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note = "Acknowledgements We acknowledge NSF funding (CHEM-0131112) for the X-ray diffractometer. We also express gratitude to Euticals for the gift of T3P in 2-methyl­tetra­hydro­furan, and to Oakwood Products for the gift of N-acetyl-L-cysteine.",
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N1 - Acknowledgements We acknowledge NSF funding (CHEM-0131112) for the X-ray diffractometer. We also express gratitude to Euticals for the gift of T3P in 2-methyl­tetra­hydro­furan, and to Oakwood Products for the gift of N-acetyl-L-cysteine.

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N2 - The asymmetric unit of the title compound, C18H18N2O2S.0.375H2O, has two independent organic molecules (A and B) and 3/4 of a water molecule distributed over three sites. In molecule A, the 1, 3-thiazine ring is in a boat conformation, with the C atoms at the 2- and 5-positions out of the plane. The angle between the two phenyl rings is 51.70 (12)°. In molecule B, the thiazine ring is in a half-chair conformation, with the S atom forming the back of the half-chair. The angle between the two phenyl rings is 84.44 (14)°. The A molecule features an intramolecular N - H⋯O hydrogen bond, which closes an S(5) ring motif. In the crystal, the corresponding N - H grouping of the B molecule participates in an intermolecular hydrogen bond to the A molecule. The A molecule participates in a C - H⋯O interaction back to the B molecule, whilst the B molecule features an intramolecular C - H⋯O link, which generates an S(10) loop.

AB - The asymmetric unit of the title compound, C18H18N2O2S.0.375H2O, has two independent organic molecules (A and B) and 3/4 of a water molecule distributed over three sites. In molecule A, the 1, 3-thiazine ring is in a boat conformation, with the C atoms at the 2- and 5-positions out of the plane. The angle between the two phenyl rings is 51.70 (12)°. In molecule B, the thiazine ring is in a half-chair conformation, with the S atom forming the back of the half-chair. The angle between the two phenyl rings is 84.44 (14)°. The A molecule features an intramolecular N - H⋯O hydrogen bond, which closes an S(5) ring motif. In the crystal, the corresponding N - H grouping of the B molecule participates in an intermolecular hydrogen bond to the A molecule. The A molecule participates in a C - H⋯O interaction back to the B molecule, whilst the B molecule features an intramolecular C - H⋯O link, which generates an S(10) loop.

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