Received 16 March 2013
aDepartment of Physics, Thanthai Periyar Government Institute of Technology, Vellore 632 002, India,bDepartment of Physics, Bharathidasan Engineering College, Nattrampalli, Vellore 635 854, India, and cDepartment of Organic Chemistry, University of Madras, Maraimalai Campus, Chennai 600 025, India
Correspondence e-mail: firstname.lastname@example.org
In the title compound, C16H11Cl2NOS, the seven-membered thiazepine ring adopts a distorted twist-boat conformation. The dihedral angle between the mean plane of the benzothiazepine ring system and the benzene ring is 78.6 (1)°. The molecular conformation is stabilized by a weak intramolecular C-HCl hydrogen bond, which generates an S(5) ring motif. In the crystal, pairs of N-HO hydrogen bonds link inversion-related molecules into dimers, generating R22(8) ring motifs. The crystal packing also features alternating - interactions between benzothiazepine benzene rings [inter-centroid distance = 3.740 (3) Å] and dichlorobenzene rings [inter-centroid distance = 3.882 (3) Å] to consolidate a three-dimensional architecture.
For background to the biology and related structures of thiazepin derivatives, see: Bakthadoss et al. (2013). For ring-puckering parameters, see: Cremer & Pople (1975). For hydrogen-bond motifs, see: Bernstein et al. (1995).
Data collection: APEX2 (Bruker, 2004); cell refinement: APEX2 and SAINT (Bruker, 2004); data reduction: SAINT and XPREP (Bruker, 2004); 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 and PLATON (Spek, 2009).
Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: TK5208 ).
The authors thank Dr Babu Vargheese, SAIF, IIT, Madras, India, for the data collection.
Bakthadoss, M., Selvakumar, R., Manikandan, N. & Murugavel, S. (2013). Acta Cryst. E69, o562-o563.
Bernstein, J., Davis, R. E., Shimoni, L. & Chang, N.-L. (1995). Angew. Chem. Int. Ed. Engl. 34, 1555-1573.
Bruker (2004). APEX2, SAINT and XPREP. Bruker AXS Inc., Madison, Wisconsin, USA.
Cremer, D. & Pople, J. A. (1975). J. Am. Chem. Soc. 97, 1354-1358.
Farrugia, L. J. (2012). J. Appl. Cryst. 45, 849-854.
Sheldrick, G. M. (1996). SADABS. University of Göttingen, Germany.
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.
Spek, A. L. (2009). Acta Cryst. D65, 148-155.