3-(3-Chlorobenzoyl)-4-hydroxy-2H-1,2-benzothiazine 1,1-dioxide

In the title compound, C15H10ClNO4S, the heterocyclic thiazine ring adopts a half-chair conformation with the S and N atoms displaced by 0.476 (5) and 0.227 (5) Å, respectively, on opposite sides of the mean plane formed by the remaining ring atoms. The structure is stabilized by intermolecular N—H⋯O and C—H⋯O hydrogen bonds. In addition, intramolecular O—H⋯O and C—H⋯N interactions are also present.

[1]  J. Jaiswal,et al.  Comparison of Analgesic and Anti-Inflammatory Activity of Meloxicam Gel with Diclofenac and Piroxicam Gels in Animal Models: Pharmacokinetic Parameters after Topical Application , 2002, Skin Pharmacology and Physiology.

[2]  Olga Kennard,et al.  Tables of bond lengths determined by X-ray and neutron diffraction. Part 1. Bond lengths in organic compounds , 1987 .

[3]  R. Blessing.  Outlier Treatment in Data Merging , 1997 .

[4]  良二 上田.  J. Appl. Cryst.の発刊に際して , 1970 .

[5]  G. Sheldrick.  A short history of SHELX. , 2008, Acta crystallographica. Section A, Foundations of crystallography.

[6]  M. Parvez,et al.  N-(X-chlorophenyl)-4-hydroxy-2-methyl-2H-1,2-benzothiazine-3-carboxamide 1,1-dioxide (with X = 2 and 4). , 2008, Acta crystallographica. Section C, Crystal structure communications.

[7]  H. Fujita.  [Anticancer drugs]. , 1995, Nihon rinsho. Japanese journal of clinical medicine.

[8]  A. Doherty,et al.  Endothelin receptor antagonists: synthesis and structure-activity relationships of substituted benzothiazine-1,1-dioxides. , 1998, Bioorganic & medicinal chemistry.

[9]  Louis J. Farrugia,et al.  ORTEP-3 for Windows - a version of ORTEP-III with a Graphical User Interface (GUI) , 1997 .

[10]  M. Sharma,et al.  Anticancer activities of 2,3-dihydro-1,4-benzothiazines, and of their 4-(N-alkyl amides) and 4-(N-alkyl N-nitrosoamides). , 1993, Anti-cancer drugs.

[11]  J. Lombardino,et al.  Sudoxicam and related N-heterocyclic carboxamides of 4-hydroxy-2H-1,2-benzothiazine 1,1-dioxide. Potent nonsteroidal antiinflammatory agents. , 1972, Journal of medicinal chemistry.

[12]  Matloob Ahmad,et al.  Anti-oxidant and anti-bacterial activities of novel N'-arylmethylidene-2-(3, 4-dimethyl-5, 5-dioxidopyrazolo[4,3-c][1,2]benzothiazin-2(4H)-yl) acetohydrazides. , 2010, European journal of medicinal chemistry.

[13]  G. G. Stokes.  "J." , 1890, The New Yale Book of Quotations.

[14]  國郎 小笠原,et al.  Chem. Pharm. Bull.(オピニオン) , 2007 .