Received 16 March 2013
aDepartment of Organic Chemistry, University of Madras, Maraimalai Campus, Chennai 600 025, India,bDepartment of Physics, Bharathidasan Engineering College, Nattrampalli, Vellore 635 854, India, and cDepartment of Physics, Thanthai Periyar Government Institute of Technology, Vellore 632 002, India
Correspondence e-mail: firstname.lastname@example.org
In the title compound, C18H17NO3S, the seven-membered thiazepine ring adopts a slightly distorted sofa conformation. The dihedral angle between the mean plane of the benzothiazepine ring system and the benzene ring is 5.9 (1)°. The molecular conformation is stabilized by an intramolecular C-HS hydrogen bond, which generates an S(7) ring motif. In the crystal, N-HO and C-HO hydrogen bonds link inversion-related molecules into dimers, incorporating R12(6) and R22(8) ring motifs; the acceptor O atom is bifurcated. These dimers are further linked by C-HO hydrogen bonds, forming supramolecular tapes running along the a axis. These are connected into the three-dimensional architecture by C-H interactions.
For the pharmaceutical properties of thiazepine derivatives, see: Tomascovic et al. (2000); Rajsner et al. (1971); Metys et al. (1965). For related structures, see: Lakshmanan et al. (2012); Selvakumar et al. (2012); Murugavel 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: TK5207 ).
The authors thank Dr Babu Vargheese, SAIF, IIT, Madras, India, for the data collection.
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.
Lakshmanan, D., Murugavel, S., Selvakumar, R. & Bakthadoss, M. (2012). Acta Cryst. E68, o2130.
Metys, J., Metysova, J. & Votava, Z. (1965). Acta Biol. Med. Ger. 15, 871-873.
Murugavel, S., Manikandan, N., Selvakumar, R. & Bakthadoss, M. (2013). Acta Cryst. E69, o564.
Rajsner, M., Protiva, M. & Metysova, J. (1971). Czech. Patent Appl. CS 143737.
Selvakumar, R., Bakthadoss, M., Lakshmanan, D. & Murugavel, S. (2012). Acta Cryst. E68, o2126.
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.
Tomascovic, L. L., Arneri, R. S., Brundic, A. H., Nagl, A., Mintas, M. & Sandtrom, J. (2000). Helv. Chim. Acta, 83, 479-493.