Research Article: (Z)-2-(5-Fluoro-2-oxoindolin-3-yl­idene)-N-phenyl­hydrazinecarbothio­amide

Date Published: February 01, 2012

Publisher: International Union of Crystallography

Author(s): Amna Qasem Ali, Naser Eltaher Eltayeb, Siang Guan Teoh, Abdussalam Salhin, Hoong-Kun Fun.


The title compound, C15H11FN4OS, crystallizes with three independent mol­ecules (A, B and C) in the asymmetric unit. The dihedral angles between the nine-membered 5-fluoro­indolin-2-one ring system and the benzene ring are 22.14 (11), 12.56 (11) and 3.70 (11)° in mol­ecules A, B and C, respectively. In all three mol­ecules, intra­molecular cyclic N—H⋯O and C—H⋯S hydrogen-bonding inter­actions [graph set S(6)] are present in the N—N—C—N chain between the ring systems. In the crystal, the A mol­ecules form centrosymmetric cyclic dimers through inter­molecular N—H⋯O hydrogen bonds, which are linked into a supramolecular chain along [100] via C—H⋯F interactions; each type of hydrogen bond has graph set graph set R22(8). A similar chain stabilised by similar interactions and also along [100] but, comprising alternating molecules of B and C is found. The latter chains are connected via C—H⋯S interactions, forming a layer with a zigzag topology parallel to (001).

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For related structures, see: Qasem Ali et al. (2011a ▶,b ▶); Ferrari et al. (2002 ▶); Pervez et al. (2010 ▶); Ramzan et al. (2010 ▶). For the biological activity of Schiff bases, see: Bhandari et al. (2008 ▶); Bhardwaj et al. (2010 ▶); Pandeya et al. (1999 ▶); Sridhar et al. (2002 ▶); Suryavanshi & Pai (2006 ▶). For the cytotoxic and anti­cancer activity of isatin and its derivatives, see: Vine et al. (2009 ▶). For graph-set analysis, see Bernstein et al. (1995 ▶).