The crystal structure of the title mixed azine, C17H17CIN2O, contains four independent molecules, A-D, and molecule B is disordered. All four molecules have an N-N gauche conformation, with C-N-N-C torsion angles of 136.5 (4), 137.0 (4), -134.7 (4) and -134.7 (4)°, respectively. The phenyl rings are also somewhat twisted with respect to the plane defined by Cipso and the imine bond. On average, the combined effect of these twists results in an angle of 64.7° between the best planes of the two phenyl rings. Arene-arene double T-contacts are the dominant intermolecular interaction. The methoxy-substituted phenyl ring of one azine molecule interacts to form a T-contact with the methoxy-substituted phenyl ring of an adjacent molecule and, similarly, two chloro-substituted phenyl rings of neighboring molecules interact to form another T-contact. The only exception is for molecule B, for which the disorder leads to the formation of T-contacts between methoxy- and chloro-substituted phenyl rings. The prevailing structural motif of T-contact formation between like-substituted arene rings results in a highly dipole-parallel-aligned crystal structure.
M. A. Lewis et al., "4-Chloroacetophenone [1-(4-Methoxyphenyl)ethylidene]Hydrazone," Acta Crystallographica Section C: Crystal Structure Communications, vol. 56, no. 3, pp. 393-396, International Union of Crystallography (IUCr), Mar 2000.
The definitive version is available at https://doi.org/10.1107/S0108270199011737
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01 Mar 2000