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

• Published in: Acta crystallographica. Section E, Crystallographic communications Vol. 76; no. Pt 5; pp. 728 - 731
• Main Authors: Ahmed, Adeeba, Ahmad, Aiman, Ahmad, Musheer, Kalibabchuk, Valentina A
• Format: Journal Article
• Language: English
• Published: England International Union of Crystallography 01-05-2020
• Subjects: Research Communications; anthracene; crystal structure; inter­molecular hydrogen bonding; Hirshfeld surface analysis; C—H⋯π inter­actions; 4-amino­benzoic acid (PABA)
• ISSN: 2056-9890; 2056-9890
• DOI: 10.1107/S2056989020005393

The title compound, C
H
NO
·C
H
NO, was synthesized by condensation of an aromatic aldehyde with a secondary amine and subsequent reduction. It was crystallized from a di-methyl-formamide solution as a monosolvate, C
H
NO
·C
H
NO. The aromatic mol-ecule is non-planar with a dihedral angle between the mean planes of the aniline moiety and the methyl anthracene moiety of 81.36 (8)°. The torsion angle of the C
-CH
-NH-C
backbone is 175.9 (2)°. The crystal structure exhibits a three-dimensional supra-molecular network, resulting from hydrogen-bonding inter-actions between the carb-oxy-lic OH group and the solvent O atom as well as between the amine functionality and the O atom of the carb-oxy-lic group and additional C-H⋯π inter-actions. Hirshfeld surface analysis was performed to qu-antify the inter-molecular inter-actions.