Received 27 December 2012
aDepartment of Chemistry, Gomal University, Dera Ismail Khan, NWFP, Pakistan,bDepartment of Chemistry, Government College University, Faisalabad 38000, Pakistan,cDepartment of Physics, University of Sargodha, Sargodha, Pakistan,dDepartment of Chemistry, University of Aberdeen, Meston Walk, Aberdeen AB24 3UE, Scotland, and eMaterials Chemistry Laboratory, Department of Chemistry, Government College University, Lahore, Pakistan
Correspondence e-mail: email@example.com
In the title compound, C16H13Cl2N3O2S, the dihedral angle between the aromatic rings is 6.62 (2)° and the C=N-N=C torsion angle is 176.2 (4)°. The thiazine ring shows an envelope conformation, with the S atom displaced by 0.633 (6) Å from the mean plane of the other five atoms (r.m.s. deviation = 0.037 Å). The Cl atom is an an axial conformation and is displaced by 2.015 (6) Å from the thiazine ring plane. In the crystal, molecules are linked by C-HO interactions, generating a three-dimensional network. Very weak aromatic - stacking interactions [centroid-centroid separations = 3.928 (2) Å] are also observed.
For background to benzothiazines, see: Misu & Togo (2003); Harmata et al. (2006). For the synthesis and biological activity of the title compound and related materials, see: Ahmad et al. (2010a); Shafiq et al. (2011a). For further synthetic details, see: Shafiq et al. (2011b). For related structures, see: Ahmad et al. (2010b); Shafiq et al. (2011c, 2013).
Data collection: APEX2 (Bruker, 2007); cell refinement: SAINT (Bruker, 2007); data reduction: SAINT; 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, 2012); software used to prepare material for publication: SHELXL97.
Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: IM2417 ).
MS acknowledges the HEC Pakistan for providing a PhD fellowship and the UOS, Sargodha, for X-ray diffraction facility.
Ahmad, M., Siddiqui, H. L., Ahmad, S., Parvez, M. & Tizzard, G. J. (2010b). J. Chem. Crystallogr. 40, 1188-1194.
Ahmad, M., Siddiqui, H. L., Zia-ur-Rehman, M. & Parvez, M. (2010a). Eur. J. Med. Chem. 45, 698-704.
Bruker (2007). APEX2, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.
Farrugia, L. J. (2012). J. Appl. Cryst. 45, 849-854.
Harmata, M., Calkins, N. L., Baughman, R. G. & Barnes, C. L. (2006). J. Org. Chem. 71, 3650-3652.
Misu, Y. & Togo, H. (2003). Org. Biomol. Chem. 1, 1342-1346.
Shafiq, M., Khan, I. U., Arshad, M. N. & Siddiqui, W. A. (2011b). Asian J. Chem. 23, 2101-2106.
Shafiq, M., Khan, I. U., Zia-ur-Rehman, M., Arshad, M. N. & Asiri, A. M. (2011c). Acta Cryst. E67, o2038.
Shafiq, M., Tahir, M. N., Harrison, W. T. A., Khan, I. U. & Shafique, S. (2013). Acta Cryst. E69, o165.
Shafiq, M., Zia-Ur-Rehman, M., Khan, I. U., Arshad, M. N. & Khan, S. A. (2011a). J. Chil. Chem. Soc. 56, 527-531.
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.