Received 24 February 2012
aInstitute of Chemistry, University of the Punjab, Lahore 54590, Pakistan,bChemistry Department, Govt. College University, Faisalabad, Pakistan, and cDepartment of Chemistry, The University of Calgary, 2500 University Drive NW, Calgary, Alberta, Canada T2N 1N4
Correspondence e-mail: email@example.com
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-HO and C-HO interactions and the crystal packing is stabilized by intermolecular O-HO and C-HCl hydrogen bonds.
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).
Data collection: COLLECT (Hooft, 1998); cell refinement: DENZO (Otwinowski & Minor, 1997); data reduction: SCALEPACK (Otwinowski & Minor, 1997); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997); software used to prepare material for publication: SHELXL97.
Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: PK2395 ).
The authors are grateful to the Higher Education Commission, Pakistan, and the Institute of Chemistry, University of the Punjab, Lahore, Pakistan, for financial support.
Ahmad, M., Siddiqui, H. L., Zia-ur-Rehman, M. & Parvez, M. (2010). Eur. J. Med. Chem. 45, 698-704.
Blessing, R. H. (1997). J. Appl. Cryst. 30, 421-426.
Farrugia, L. J. (1997). J. Appl. Cryst. 30, 565.
Hooft, R. (1998). COLLECT. Nonius BV, Delft, The Netherlands.
Otwinowski, Z. & Minor, W. (1997). Methods in Enzymology, Vol. 276, Macromolecular Crystallography, Part A, edited by C. W. Carter Jr & R. M. Sweet, pp. 307-326. New York: Academic Press.
Rajagopal, R. & Seshadri, S. (1990). Dyes Pigm. 13, 93-105.
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.
Siddiqui, W. A., Ahmad, S., Khan, I. U., Siddiqui, H. L. & Weaver, G. W. (2007). Synth. Commun. 37, 767-773.
Siddiqui, W. A., Ahmad, S., Tariq, M. I., Siddiqui, H. L. & Parvez, M. (2008). Acta Cryst. C64, o4-o6.
Turck, D., Busch, U., Heinzel, G., Narjes, H. & Nehmiz, G. (1995). Clin. Drug Invest. 9, 270-276.
Zia-ur-Rehman, M., Choudary, J. A., Ahmad, S. & Siddiqui, H. L. (2006). Chem. Pharm. Bull. 54, 1175-1178.