The title molecule, 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. Intramolecular N—H⋯O and N—H⋯N hydrogen bonds form S(6) and S(5) ring motifs, respectively. In the crystal, molecules are assembled into inversion dimers through pairs of co-operative N—H⋯Cl interactions. 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 interactions [centroid–centroid distance = 3.849 (2) Å].
The title molecule, C5H5N5O3S, is approximately planar, with a maximum deviation from the mean plane through the non-H atoms of 0.182 (3) Å for the amine N atom. In the crystal, molecules are connected via N—H⋯O and N—H⋯S interactions, building a three-dimensional hydrogen-bonded network. Additionally, a weak intramolecular N—H⋯O hydrogen bond is observed.
The reaction between 5-cholroisatin and phenylhydrazine yields the title compound, C 14 H 10 ClN 3 O. The molecular structure deviates slightly from the ideal planarity, with an r.m.s. deviation of 0.1372 (12) Å for the non-H atoms. An N-HÁ Á ÁO intramolecular interaction is observed, which supports an E conformation with respect to the C N bond. In the crystal, molecules are linked by a pair of N-HÁ Á ÁO interactions into an inversion dimer. The dimers are linked by weak C-HÁ Á ÁCl interactions, formng a tape structure along [101]. The tapes are also linked through a weak -interaction [centroid-centroid distance = 3.5773 (8) Å ] into a layer parallel to (111). An in silico evaluation of the title compound with a topoisomerase enzyme was performed and the global free energy of À26.59 kJ mol À1 was found.
Structure descriptionThe chemistry of isatin derivatives covers a wide range of scientific disciplines with special attention to medicinal chemistry (Vine et al., 2013). As part of our ongoing research into isatin derivatives, we report herein the crystal structure of the title compound (common name: 5-chloroisatine-3-phenylhydrazone). The title molecule is nearly planar, with the r.m.s. deviation for the non-H atoms being 0.1372 (12) Å for atom C11 (Fig. 1). In the crystal, molecules are linked by N-HÁ Á ÁO and weak C-HÁ Á ÁCl interactions (Table 1) into a hydrogen-bonded tape structure along [101] (Fig. 2). In addition, a weak -interaction between the pyrrole and phenyl rings [centroid-centroid distance = 3.5773 (8) Å ] connects the tapes, forming a layer parallel to
In the title compound, C9H7FN4OS, the molecules are almost planar, with an r.m.s. deviation of 0.047 (3) Å from the mean plane defined by the non-H atoms and a maximum deviation of 0.123 (2) Å for the amine N atom. The torsion angle for the N—N—C—S unit is 176.57 (19)°. In the crystal, molecules are linked into inversion dimers via pairs of N—H⋯F hydrogen bonds and, additionally, through N—H⋯O and N—H⋯S hydrogen bonds, building a two-dimensional hydrogen-bond network parallel to the (103) plane. An intramolecular N—H⋯O interaction is also observed.
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