Single crystal structure, Hirshfeld surface analysis and DFT studies on 2‑bromo-4‑chloro-6-[(2‑hydroxy-5-methylanilino)methylidene]cyclohexa-2,4-dienone

A new crystal compound, 2‑bromo-4‑chloro-6-[(2‑hydroxy-5-methylanilino)methylidene]cyclohexa-2,4-dienone (Compound 1) was experimentally characterized by infrared, UV–Visible spectroscopy and single crystal X-ray diffraction technique. We report herein the synthesis, characterization of single crystal structure, DFT, natural bond orbital, linear and nonlinear optical properties studies of compound 1. The experimental data of UV–Visible, IR and X-ray and calculated data obtained from TD-DFT and DFT methods were compared and discussed in detail. The UV–Visible, IR and X-ray data revealed that the studied compound exists as keto-amine form. Compound 1 was crystallized in the monoclinic crystal system in the space group C2/c (#15) with chemical formula C₁₄H₁₁BrClNO₂. The crystal geometry of compound 1 was stabilized by hydrogen bond and weak π–π interactions. The 97.58% Lewis structure and 2.42% non-Lewis structure were found in the studied molecular system.