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

Amna Qasem Ali,Naser Eltaher Eltayeb,Abdussalam Salhin,Hoong-Kun Fun,Siang Guan Teoh

doi:10.1107/s160053681105433x

Abstract

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 R 2 2(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).

Highlights

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
The A molecules form centrosymmetric cyclic dimers through intermolecular N—H O hydrogen bonds, which are linked into a supramolecular chain along [100] via

Summary

Structure Reports

The title compound, C15H11FN4OS, crystallizes with three independent molecules (A, B and C) in the asymmetric unit. C—H S hydrogen-bonding interactions [graph set S(6)] are present in the N—N—C—N chain between the ring systems. 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 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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