Received 19 December 2012
aDepartment of Chemistry, Government College University, Faisalabad 38000, Pakistan,bDepartment of Physics, University of Sargodha, Sargodha, Pakistan,cDepartment of Chemistry, University of Aberdeen, Mston Walk, Aberdeen AB24 3UE, Scotland, and dMaterials Chemistry Laboratory, Department of Chemistry, Government College University, Lahore, Pakistan
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In the title compound, C18H16ClN3O2S, the dihedral angle between the aromatic rings is 4.81 (2)° and the alkyl chain takes on an extended conformation [N-C-C-C = 179.2 (4)°]. The conformation of the thiazine ring is an envelope, with the S atom displaced by -0.805 (3) Å from the mean plane of the other five atoms (r.m.s. deviation = 0.046 Å). The Cl atom is an axial conformation and is displaced by 1.761 (4) Å from the thiazine ring plane. In the crystal, inversion dimers linked by pairs of C-HO interactions generate R22(20) loops and further C-HO hydrogen bonds link the dimers into (001) sheets. Weak aromatic - stacking interactions [centroid-centroid separations = 3.870 (3) and 3.883 (3) Å] are also observed.
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 (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: BQ2381 ).
MS acknowledges the HEC Pakistan for granting a PhD fellowship.
Bruker (2007). APEX2, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.
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Shafiq, M., Zia-Ur-Rehman, M., Khan, I. U., Arshad, M. N. & Khan, S. A. (2011a). JJ. Chil. Chem. Soc. 56, 527-531.
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.