Methyl 2-acetonyl-4-hydroxy-2<i>H</i>-1,2-benzothiazine-3-carboxylate 1,1-dioxide

Arshad, Muhammad Nadeem; Zia‐ur‐Rehman, Muhammad; Khan, Islam Ullah

doi:10.1107/s1600536808019156

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“…For the biological properties and synthetic details of the title compound, see: Parveen et al (2014). For related structures, see: Ahmad et al (2008); Zia-ur-Rehman et al (2008); Yang et al (2012). For graph-set analysis, see: Etter et al (1990).…”

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confidence: 99%

2-[(Z)-1,1-Dioxo-2-(2,4,5-trifluorobenzyl)-3,4-dihydro-2H-1,2-benzothiazin-4-ylidene]acetic acid

et al. 2014

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In the title compound, C17H12F3NO4S, the heterocyclic thiazine ring adopts a half-chair conformation and the dihedral angle between the benzene rings is 43.28 (9)°. The α,β-unsaturated C=C group is inclined at an angle of 21.0 (3)° to the benzene ring of the benzothiazine moiety. In the crystal, inversion dimers linked by pairs of carboxylic acid O—H⋯O hydrogen bonds generate R 2 2(8) loops. Each of the F atoms accepts a Ca—H⋯F (a = aromatic) hydrogen bond from an adjacent molecule, resulting in (001) sheets.

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Section: Related Literaturementioning

confidence: 99%

2-[(Z)-1,1-Dioxo-2-(2,4,5-trifluorobenzyl)-3,4-dihydro-2H-1,2-benzothiazin-4-ylidene]acetic acid

et al. 2014

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2-[1,1-Dioxo-2-(2,4,5-trifluorobenzyl)-2H-1,2-benzothiazin-4-yl]acetic acid

Yang

Zhu

2012

Acta Cryst E

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In the title compound, C17H12F3NO4S, the heterocyclic thiazine ring adopts a half-chair conformation with the S and the N atoms displaced by −0.608 (3) and 0.105 (3) Å, respectively, from the mean plane formed by the remaining ring atoms. The dihedral angle between the two benzene rings is 36.63 (8)° and the acetic acid group is inclined at right angles [89.78 (8) °] to the mean plane formed by the C atoms of the thiazine ring. The crystal structure features O—H⋯O and C—H⋯O hydrogen bonds.

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Methyl 2-acetonyl-4-hydroxy-2H-1,2-benzothiazine-3-carboxylate 1,1-dioxide

Abstract: In the molecule of the title compound, C13H13NO6S, the thiazine ring adopts a distorted sofa conformation. The enolic H atom is involved in intramolecular O—H⋯O hydrogen bonding besides the weaker C—H⋯O=S and C—H⋯O=C interactions.

Cited by 2 publications

References 15 publications

2-[(Z)-1,1-Dioxo-2-(2,4,5-trifluorobenzyl)-3,4-dihydro-2H-1,2-benzothiazin-4-ylidene]acetic acid

2-[(Z)-1,1-Dioxo-2-(2,4,5-trifluorobenzyl)-3,4-dihydro-2H-1,2-benzothiazin-4-ylidene]acetic acid

2-[1,1-Dioxo-2-(2,4,5-trifluorobenzyl)-2H-1,2-benzothiazin-4-yl]acetic acid

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Methyl 2-acetonyl-4-hydroxy-2H-1,2-benzothiazine-3-carboxylate 1,1-dioxide

Abstract: In the mol­ecule of the title compound, C13H13NO6S, the thia­zine ring adopts a distorted sofa conformation. The enolic H atom is involved in intra­molecular O—H⋯O hydrogen bonding besides the weaker C—H⋯O=S and C—H⋯O=C inter­actions.

Cited by 2 publications

References 15 publications

2-[(Z)-1,1-Dioxo-2-(2,4,5-trifluorobenzyl)-3,4-dihydro-2H-1,2-benzothiazin-4-ylidene]acetic acid

2-[(Z)-1,1-Dioxo-2-(2,4,5-trifluorobenzyl)-3,4-dihydro-2H-1,2-benzothiazin-4-ylidene]acetic acid

2-[1,1-Dioxo-2-(2,4,5-trifluorobenzyl)-2H-1,2-benzothiazin-4-yl]acetic acid

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Abstract: In the molecule of the title compound, C13H13NO6S, the thiazine ring adopts a distorted sofa conformation. The enolic H atom is involved in intramolecular O—H⋯O hydrogen bonding besides the weaker C—H⋯O=S and C—H⋯O=C interactions.