Crystal structure and Hirshfeld surface analysis, crystal voids, interaction energy calculations and energy frameworks of C-anthracen-9-yl-N-methyl aldonitrone

The title compound (systematic name: 1-anthracen-9-yl-N-methylmethanimine oxide), C₁₆H₁₃NO, contains an almost planar anthracene ring system [r.m.s. deviation = 0.021 (1) Å]. In the crystal, intermolecular bifurcated C-H· · ·O hydrogen bonds link the molecules into infinite chains along the a-axis direction. The π-π stacking interactions between the benzene rings of adjacent molecules help to consolidate the three-dimensional architecture. The Hirshfeld surface analysis of the crystal structure indicates that the most important contributions for the crystal packing are from H· · ·H (54.5%), H· · ·C/C· · ·H (23.7%), H· · ·O/ O· · ·H (10.6%) and C· · ·C (9.8%) interactions. The volume of the crystal voids and the percentage of free space were calculated to be 76.07 ų and 6.57%, respectively, showing that there is no large cavity in the crystal packing. Evaluation of the electrostatic, dispersion and total energy frameworks indicates that the stabilization largely depends on dispersion energy contributions. Hydrogen bonding, π-π and van der Waals interactions, together with the dispersion energy contributions, are the dominant interactions in the crystal packing.