Date Published: July 01, 2012
Publisher: International Union of Crystallography
Author(s): Hatem A. Abdel-Aziz, Tze Shyang Chia, Hoong-Kun Fun.
The title compound, C9H9ClN2O, is close to planar (r.m.s. deviation for the non-H atoms = 0.0446 Å); it exists in a cis conformation with respect to the C=N double bond. In the crystal, the ketone O atom accepts both N—H⋯O and C—H⋯O hydrogen bonds, which leads to  infinite chains incorporating R21(6) loops. The crystal structure also features a C—H⋯π interaction.
For synthetic applications of hydrazonoyl chlorides, see: Abdel-Aziz & Mekawey (2009 ▶). For graph-set descriptors of hydrogen-bond motifs, see: Bernstein et al. (1995 ▶). For related structures. see: Asiri et al. (2011a ▶,b ▶). For a historical perspective on the synthesis, see: Dieckmann & Platz (1905 ▶). For the stability of the temperature controller used in the data collection, see: Cosier & Glazer (1986 ▶).