Crystal structure and Hirshfeld surface analysis of ( <i>E</i> )-2-[(anthracen-9-ylmethylidene)amino]-4-nitroaniline

Abstract

The title compound, C 21 H 15 N 3 O 2 , contains a nitroaniline ring and an anthracene ring system bridged over the methylene amino group. The anthracene ring system is essentially planar with an r.m.s. deviation of 0.03 (2) Å and it is oriented at a dihedral angle of 79.70 (5)° with respect to nitroaniline ring. There is an intramolecular N—H...N hydrogen bond between N atoms of nitroaniline ring and amino group. In the crystal, N—H—O hydrogen bonds link the molecules into infinite chains along the b -axis direction. π–π stacking interactions between the nitroaniline rings of adjacent molecules with centroid-to-centroid distance of 3.7682 (2) Å and C—H...π(ring) interactions may help to consolidate the three-dimensional architecture. A Hirshfeld surface analysis indicates that the most important contributions for the crystal packing are from H...H (35.5%), H...C/C...H (33.7%) and H...O/O...H (18.3%) interactions.