Synthesis, crystal structure and Hirshfeld surface analysis of 2-chloro-3-[(E)-(2-phenyl-hydrazinyl-idene)meth-yl]quinoline.

ABSTRACT: A new quinoline-based hydrazone, C₁₆H₁₂ClN₃, was synthesized by a condensation reaction of 2-chloro-3-formyl-quinoline with phenyl-hydrazine. 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 mol-ecule adopts an E configuration with respect to the central C=N bond. In the crystal, mol-ecules are linked by a C-H??-phenyl inter-action, forming zigzag chains propagating along the [10] direction. The N-H hydrogen atom does not participate in hydrogen bonding but is directed towards the phenyl ring of an adjacent mol-ecule, so linking the chains via weak N-H?? inter-actions 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.

SUBMITTER: Akhramez S 

PROVIDER: S-EPMC6659329 | biostudies-literature | 2019 Jul

REPOSITORIES: biostudies-literature