Crystal structure and Hirshfeld surface analysis of 4-{[(anthracen-9-yl)methyl]amino}benzoic acid

Abstract

In the molecule of the title anthracene derivative, C22H17NO2, the benzene ring is inclined to the mean plane of the anthracene ring system (r.m.s. deviation = 0.024 Å) by 75.21 (9)°. In the crystal, molecules are linked by pairs of O—H...O hydrogen bonds, forming classical carboxylic acid inversion dimers with an R 2 2(8) ring motif. The dimers are linked by C—H...π interactions, forming a supramolecular framework.

Crystal structure and Hirshfeld surface analysis of 4-{[(anthracen-9-yl)methyl]amino}benzoic acid dimethylformamide monosolvate

“…The torsion angle of the C aryl -CH 2 -NH-C aryl backbone (C9-C8-N1-C5) is 175.9 (2) . The C8-N1 bond length of 1.452 (3) Å is in agreement with the corresponding bond length of 1.457 (3) Å in the solvent-free compound [CSD (Groom et al, 2016) refcode RUCJIL; Ahmed et al, 2020], just as the bond lengths in the carboxylic group of the title compound, C1-O2 = 1.230 (3), C1-O1 = 1.322 (3) Å , are virtually identical with those of the solvent-free compound [1.238 (3) and 1.325 (3) Å , respectively].…”

“…The Schiff base was synthesized and subsequently reduced by a reported procedure (Ahmed et al, 2020). To this reduced ligand (0.15 mmol), ethanol and dimethylformamide were added in an equal volume ratio, and the mixture was heated under reflux for 3-4 h at 353 K. The solution was then allowed to cool to room temperature, filtered and kept for slow evaporation.…”

Crystal Structure, Topology, DFT and Hirshfeld Surface Analysis of a Novel Charge Transfer Complex (L3) of Anthraquinone and 4-{[(anthracen-9-yl)meth-yl] amino}-benzoic Acid (L2) Exhibiting Photocatalytic Properties: An Experimental and Theoretical Approach

“…The ligand (L2) was synthesized by an earlier reported procedure [ 10 ]. Both ligand (L2) and anthraquinone were taken in 1:1 ratio; L2 (0.459 mmol, 0.015 g) and anthraquinone (0.0459 mmol, 0.0095 g) were placed in a 100 mL round-bottom flask and dissolved in a solvent of ethanol and water in a ratio of 1:0.5, and the mixture was refluxed at 80 °C for 2 h. A clear yellow-colored solution obtained was allowed to cool and kept for slow evaporation after filtration ( Scheme 1 ).…”

“…The existence of hydrogen bonding and non-covalent interactions make them obtain more attention in the emerging field of supramolecular chemistry [ 8 , 9 ]. Donor–acceptor molecular systems are also parts of these kinds of systems, and in this respect, we have synthesized a new donor–acceptor system (L3) by synthesizing our own ligand (L2) [ 10 ] as donor and anthraquinone as an acceptor molecule. Anthraquinone has been an important chemical for pharmaceutical preparations [ 11 ].…”