Received 2 July 2013
aEscola de Química e Alimentos, Universidade Federal do Rio Grande, Av. Itália km 08, Campus Carreiros, 96203-903 Rio Grande, RS, Brazil,bInstitut für Anorganische Chemie, Christian-Albrechts-Universität zu Kiel, Max-Eyth Strasse 2, D-24118 Kiel, Germany, and cDepartamento de Química, Universidade Federal de Sergipe, Av. Marechal Rondon s/n, Campus, 49100-000 São Cristóvão, SE, Brazil
Correspondence e-mail: firstname.lastname@example.org
In the title compound, C15H11BrN4OS, the least-squares plane through the 5-bromoisatin fragment forms a dihedral angle of 13.63 (14)° with the phenyl ring. The molecular conformation features intramolecular N-HN and N-HO hydrogen bonds. In the crystal, molecules are connected via pairs of N-HO interactions into centrosymmetric dimers. Additionally, - stacking interactions link molecules into chains parallel to the a axis with short CC distances being observed between the phenyl and thiocarbonyl [3.236 (8) Å] groups and between the thiocarbonyl and carbonyl [3.351 (4) Å] groups of stacked molecules.
For the pharmacological properties of isatin-thiosemicarbazone derivatives against cruzain, falcipain-2 and rhodesain, see: Chiyanzu et al. (2003). For the synthesis of 5-bromoisatin-3-thiosemicarbazone, see: Campaigne & Archer (1952). For the crystal structure of 1-(5-bromo-2-oxoindolin-3-ylidene)thiosemicarbazide acetonitrile monosolvate, see: Pederzolli et al. (2011).
Data collection: X-AREA (Stoe & Cie, 2008); cell refinement: X-AREA; data reduction: X-RED32 (Stoe & Cie, 2008); 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: FY2102 ).
We gratefully acknowledge financial support by the State of Schleswig-Holstein, Germany. We thank Professor Dr. Wolfgang Bensch for access to his experimental facilities. We gratefully acknowledge financial support through the DECIT/SCTIE-MS-CNPq-FAPERGS-Pronem-# 11/2029-1 and PRONEX-CNPq-FAPERGS projects. KCTB thanks FAPEAM for the award of a scholarship and ABO acknowledges financial support through the FAPITEC/SE/FUNTEC/CNPq PPP 04/2011 program.
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