Synthesis, crystal structure and Hirshfeld surface analysis of 2-chloro-3-[(E)-(2-phenylhydrazinylidene)methyl]quinoline

Abstract

A new quinoline-based hydrazone, C16H12ClN3, was synthesized by a condensation reaction of 2-chloro-3-formylquinoline with phenylhydrazine. The quinoline ring system is essentially planar (r.m.s. deviation = 0.012 Å), and forms a dihedral angle of 8.46 (10)° with the phenyl ring. The molecule adopts an E configuration with respect to the central C=N bond. In the crystal, molecules are linked by a C—H...π-phenyl interaction, forming zigzag chains propagating along the [10\overline{3}] direction. The N—H hydrogen atom does not participate in hydrogen bonding but is directed towards the phenyl ring of an adjacent molecule, so linking the chains via weak N—H...π interactions to form of a three-dimensional structure. The Hirshfeld surface analysis of the crystal structure indicates that the most important contributions to the crystal packing are from H...H (35.5%), C...H/H...C (33.7%), Cl...H/H...Cl (12.3%), N...H/H...N (9.5%) contacts.

Keywords

• crystal structure
• quinoline hydrazine
• phenyl hydrazine
• C—H...π interaction
• weak N—H...π interaction
• Hirshfeld surface analysis