In the title compound, C 8 H 5 ClN 2 O 2 (common name: 5-chloroisatin 3-oxime), the molecular structure deviates slightly from the ideal planarity, with a maximum deviation of 0.0478 (8) Å for the non-H atoms. In the crystal, molecules are linked by N-HÁ Á ÁO interactions, building centrosymmetric dimers with graph-set motif R 2 2 (8). Additionally, the molecules are connected by pairs of O-HÁ Á ÁO interactions into chains along [100] with a C(6) motif. The hydrogen-bonded dimers and chains build a two-dimensional network parallel to (100). The packing also features -stacking interactions between benzene rings [centroid-centroid distance = 3.748 (2) Å ]. Structure descriptionAs part of our study on the structural chemistry of isatin derivatives we report herein the crystal structure of 5-chloroisatin-3-oxime (for the asymmetric unit, see Fig. 1). The title compound is almost planar with an r.m.s. maximum deviation for the non-H atoms of 0.0478 (8) Å for O2. In the solid state, the molecules are connected into dimers via pairs of N1-H1Á Á ÁO1 interactions and a graph-set motif R 2 2 (8) is observed. In addition, the molecules are connected into chains with a C(6) graph-set motif by O2-H5Á Á ÁO1 hydrogen bonds (Fig. 2 and Table 1). The O-HÁ Á ÁO interactions connect the centrosymmetric dimers building a two-dimensional network, a tape structure, parallel to (100). As the outstanding feature, the ketone oxygen atom, O1, accepts two hydrogen bonds. As the difference between the two HÁ Á ÁO distances is less than 0.2 Å , the hydrogen bonds presumably have roughly equal strength and the arrangement may be described as symmetric. The packing also features -stacking interactions between benzene rings [centroid-centroid distance = 3.748 (2) A ].
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
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