Received 11 November 2013
aEscola de Quimica e Alimentos, Universidade Federal do Rio Grande, Av. Italia, km 08, Campus Carreiros, 96203-900 Rio Grande-RS, Brazil, and bDepartamento de Quimica, Universidade Federal de Santa Maria, Av. Roraima, Campus, 97105-900 Santa Maria-RS, Brazil
Correspondence e-mail: email@example.com
The title molecule, C9H7ClN4OS, is almost planar, with an r.m.s. deviation of 0.034 (2) Å for the mean plane through all the non-H atoms. Intramolecular N-HO and N-HN hydrogen bonds form S(6) and S(5) ring motifs, respectively. In the crystal, molecules are assembled into inversion dimers through pairs of co-operative N-HCl interactions. These dimers are connected along the b axis by N-HO and N-HS hydrogen bonds, generating layers parallel to (103). The layers are further connected along the a axis into a three-dimensional network, through weak - stacking interactions [centroid-centroid distance = 3.849 (2) Å].
For the synthesis of the title compound, see: Qasem Ali et al. (2011). For similar hydrazinecarbothioamide crystal structures, see: Bandeira et al. (2013); Ali et al. (2012); de Oliveira et al. (2012). For the biological activity of isatin and derivatives, see: Cerchiaro & Ferreira (2006).
Data collection: APEX2 (Bruker, 2009); cell refinement: SAINT (Bruker, 2009); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: DIAMOND (Brandenburg, 2006); software used to prepare material for publication: publCIF (Westrip, 2010).
Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: LR2119 ).
We gratefully acknowledge Professor Dr. Manfredo Hörner (Federal University of Santa Maria, Brazil) for his help and support with the X-ray measurements. We also acknowledge financial support through the DECIT/SCTIE-MS-CNPq- FAPERGS-Pronem-# 11/2029-1 and PRONEX-CNPq- FAPERGS projects.
Ali, A. Q., Eltayeb, N. E., Teoh, S. G., Salhin, A. & Fun, H.-K. (2012). Acta Cryst. E68, o2868-o2869.
Bandeira, K. C. T., Bresolin, L., Näther, C., Jess, I. & Oliveira, A. B. (2013). Acta Cryst. E69, o1251-o1252.
Brandenburg, K. (2006). DIAMOND. Crystal Impact GbR, Bonn, Germany.
Bruker (2009). APEX2, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.
Cerchiaro, G. & Ferreira, A. M. C. (2006). J. Braz. Chem. Soc. 17, 1473-1485.
Oliveira, A. B. de, Silva, C. S., Feitosa, B. R. S., Näther, C. & Jess, I. (2012). Acta Cryst. E68, o2581.
Qasem Ali, A., Eltayeb, N. E., Teoh, S. G., Salhin, A. & Fun, H.-K. (2011). Acta Cryst. E67, o3141-o3142.
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.
Westrip, S. P. (2010). J. Appl. Cryst. 43, 920-925.