Structural and Theoretical Investigations, Hirshfeld Surface Analyses, and Cytotoxicity of a Naphthalene-Based Chiral Compound

A novel
Schiff base compound derived from the condensation of 2-hydroxy-1-naphthaldehyde
with (1S,2S)-(−)-1,2-diphenylethylenediamine
in 2:1 M ratio was reported and investigated by elemental analyses,
Fourier transform infrared and NMR spectroscopic studies, and single-crystal
X-ray crystallography. Hirshfeld surface analyses were also carried
out to measure the various intermolecular contacts controlling the
supramolecular topology, suggesting the H···O (7.6%)
contacts to be the most significant interactions, whereas the H···H
(48.9%) and C···H (40.2%) interactions are less-significant.
The data obtained from the energy calculations revealed the structure
observed experimentally to be the most stable isomer and its energy
being lower by 18.0441 kcal/mol than the less stable one. Density
functional theory calculations were also carried out to analyze the
natural charges, reactivity descriptors, and different intramolecular
charge transfer interactions. The in vitro anticancer
activity of the compound was evaluated by MTT assays against human
colorectal cancer cells, HT-29 and SW620. The results showed that
the compound has potential anticancer activity against these cells
lines.