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.

Water-Tolerant Hydrogen-Bonded Organic Framework Based on Phenylbis(benzimidazol-2-yl)methanol: Synthesis, Structural Characterization, and Organic-Vapor-Adsorption Properties

“…Therefore, we decided to analyze the interactions between the NH site and six-membered rings in detail. The distances from the hydrogen atom of the NH site, which was placed according to the residual peaks of the electron density (N–H distance of 0.88(5) Å (not restrained)), to the six-membered rings (2.61(5) and 2.83(5) Å; Figure a) and the angles formed by the N–H bond and the line perpendicular to the six-membered rings from the hydrogen atom (134(3)° and 108(3)°; Figure a) are within the range previously reported for several organic crystals that have been reported to form weak N–H···π interactions (2.35(2)–3.01(5) Å, average 2.66(22); 107(3)–166.32(18)°, average 143(18)°). − We also performed a Hirshfeld surface analysis for the surface of the NH site using CrystalExplorer . Blue-colored highlights pointing toward the six-membered rings were observed from the NH site (Figure b, left), suggesting the presence of contacts longer than the van der Waals contact .…”

Synthesis, crystal growth, characterization and DFT investigation of a nonlinear optically active cuminaldehyde derivative hydrazone

“…The Hirshfeld surfaces of IBIHM are displayed in Fig. 7, illustrating surfaces that have been mapped over shape index, curvedness, d norm , d e and d i (Anitha et al, 2019;Akhramez et al, 2019). The surfaces are shown as transparent to permit visualization of the IBIHM molecule around which they were calculated.…”