2-(5-Chloro-2-oxoindolin-3-yl-idene)hydrazinecarbo-thio-amide

Abstract

The title mol-ecule, 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. Intra-molecular N-H⋯O and N-H⋯N hydrogen bonds form S(6) and S(5) ring motifs, respectively. In the crystal, mol-ecules are assembled into inversion dimers through pairs of co-operative N-H⋯Cl inter-actions. These dimers are connected along the b axis by N-H⋯O and N-H⋯S hydrogen bonds, generating layers parallel to (103). The layers are further connected along the a axis into a three-dimensional network, through weak π-π stacking inter-actions [centroid-centroid distance = 3.849 (2) Å].

Fig. 1.

Molecular projection showing the asymmetric unit. Intramolecular hydrogen bonds are represented with dashed lines. Ellipsoid probability: 50%.

Fig. 2.

Bi-dimensional network formed through intermolecular hydrogen bonds, represented with dashed lines. Aromatic hydrogen atoms were omitted for clarity. Symmetry codes: (i) –x + 2, –y + 1, –z; (ii) –x + 1/2, y + 1/2, –z + 1/2; (iii) –x + 1/2, y - 1/2, –z + 1/2.

Fig. 3.

Packing of bidimensional layers through π–π stacking interactions. Aromatic hydrogen atoms were omitted for clarity. Symmetry codes: (iv) x + 1/2, –y + 3/2, z + 1/2; (v) x – 1/2, –y + 3/2, z + 1/2.