2,6-Dichloro-aniline-4-(2,6-dichloro-anilino)-pent-3-en-2-one (1/2)

Abstract

The asymmetric unit of the title compound, C6H5Cl2N·2C11H11Cl2NO, is composed of one mol-ecule of an enamino-ketone [i.e. -(2,6-dichloro-phenyl-amino)-pent-3-en-2-one] and half a mol-ecule of 2,6-dichloro-aniline, the whole mol-ecule of the latter component being generated by twofold rotational symmetry. In this latter mol-ecule, there are two intra-molecular N-H⋯Cl contacts. In the enamino-ketone mol-ecule, there is an N-H⋯O hydrogen bond of moderate strength, and the dihedral angle between the benzene ring and penta-none fragment [C-C(-N)=C-C(=O)-C; planar within 0.005 (1) Å] is 81.85 (7)°. In the crystal, two mol-ecules of the enamino-ketone are bridged by a mol-ecule of 2,6-dichloro-aniline via N-H⋯O hydrogen bonds of moderate strength. There are also π-π inter-actions present, involving the benzene rings of inversion-related enamino-ketone mol-ecules [centroid-centroid distance = 3.724 (4) Å].

Fig. 1.

The molecular structure of the title compound, with the atom numbering. The displacement ellipsoids are drawn at the 50% probability level [Symmetry code: (i) -x, y, -z + 1/2]. The various intramolecular hydrogen bonds and contacts are shown as dashed lines.

Fig. 2.

A view of the unit cell along the b axis of the crystal structure of the title compound, illustrating the intra- and intermolecular N—H···O hydrogen bonds (dashed yellow lines).