(Z)-2-(5-Chloro-2-oxoindolin-3-ylidene)-N-phenylhydrazinecarbothioamide

In the title compound, C15H11ClN4OS, the dihedral angle between the nine-membered 5-chloroindolin-2-one ring system and the benzene ring is 10.00 (6)°. 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, molecules form centrosymmetric cyclic dimers through intermolecular N—H⋯O hydrogen bonds [graph-set R 2 2(8)] and are extended by C—H⋯Cl interactions into infinite chains which propagate along [100].

[1]  N. Pai,et al.  Synthesis and Antibacterial Screening of N‐[Naphtho[1,2‐b]pyrano [3,4‐d]thiazol‐8‐yl]spiroindoloazetidin‐2‐ones/thiazolidin‐4‐ones. , 2006 .

[2]  Muhammad Nawaz Tahir,et al.  1-(2-Oxoindolin-3-ylidene)-4-[2-(trifluoromethyl)phenyl]thiosemicarbazide , 2010, Acta crystallographica. Section E, Structure reports online.

[3]  M. C. Rodríguez-Argüelles,et al.  Preparation, characterization and X-ray structures of 1-methylisatin 3-thiosemicarbazone copper, nickel and cobalt complexes , 2002 .

[4]  G. Sheldrick.  A short history of SHELX. , 2008, Acta crystallographica. Section A, Foundations of crystallography.

[5]  4-(3-Nitrophenyl)-1-(2-oxoindolin-3-ylidene)thiosemicarbazide , 2010, Acta crystallographica. Section E, Structure reports online.

[6]  D. Sriram,et al.  Synthesis, Antibacterial, Antifungal And Anti-HIV Activity Of Schiff And Mannich Bases Of Isatin With N-[6-Chlorobenzothiazol-2-yl] Thiosemicarbazide , 1999 .

[7]  K. Bothara,et al.  Design, synthesis and evaluation of antiinflammatory, analgesic and ulcerogenicity studies of novel S-substituted phenacyl-1,3,4-oxadiazole-2-thiol and Schiff bases of diclofenac acid as nonulcerogenic derivatives. , 2008, Bioorganic & medicinal chemistry.

[8]  Raymond E. Davis,et al.  Patterns in Hydrogen Bonding: Functionality and Graph Set Analysis in Crystals , 1995 .

[9]  D. Skropeta,et al.  Cytotoxic and anticancer activities of isatin and its derivatives: a comprehensive review from 2000-2008. , 2009, Anti-cancer agents in medicinal chemistry.

[10]  Anthony L. Spek,et al.  Structure validation in chemical crystallography , 2009, Acta crystallographica. Section D, Biological crystallography.

[11]  J. Stables,et al.  Anticonvulsant activity of hydrazones, Schiff and Mannich bases of isatin derivatives. , 2002, European journal of pharmaceutical sciences : official journal of the European Federation for Pharmaceutical Sciences.

[12]  ダニエル エル． フリン,et al.  Anti-cancer agents , 2003 .

[13]  H. Fun,et al.  (Z)-N-Methyl-2-(5-nitro-2-oxoindolin-3-ylidene)hydrazinecarbothioamide , 2012, Acta crystallographica. Section E, Structure reports online.

[14]  Olga Kennard,et al.  Tables of bond lengths determined by X-ray and neutron diffraction. Part 1. Bond lengths in organic compounds , 1987 .

[15]  H. Flack,et al.  On enantiomorph‐polarity estimation , 1983 .