Research Article: 1-(4-Chloro­phen­yl)-2-[4-hy­droxy-3-(3-meth­oxy­benzo­yl)-1,1-dioxo-2H-1λ6,2-benzothia­zin-2-yl]ethanone

Date Published: April 01, 2012

Publisher: International Union of Crystallography

Author(s): Hamid Latif Siddiqui, Matloob Ahmad, Salman Gul, Chaudhary Muhammad Ashraf, Masood Parvez.


In the title mol­ecule, C24H18ClNO6S, the heterocyclic thia­zine ring adopts a half-chair conformation with the S and N atoms displaced by 0.406 (5) and 0.444 (5) Å, respectively, on opposite sides of the mean plane formed by the remaining ring atoms. The meth­oxy­benzoyl and the chloro­phenyl rings lie roughly parallel to each other, with a dihedral angle between the mean planes of these rings of 8.86 (10)°. The mol­ecular structure is consolidated by intra­molecular O—H⋯O and C—H⋯O inter­actions and the crystal packing is stabilized by inter­molecular O—H⋯O and C—H⋯Cl hydrogen bonds.

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For background information on the synthesis of related compounds, see: Siddiqui et al. (2007 ▶). For the biological activity of benzothia­zine derivatives, see: Turck et al. (1995 ▶); Zia-ur-Rehman et al. (2006 ▶); Ahmad et al. (2010 ▶). For studies of benzothia­zines as precursors for azodisperse dyes for polyesters, see: Rajagopal & Seshadri (1990 ▶). For a related structure, see: Siddiqui et al. (2008 ▶).