Synthesis, crystal structure, characterization, Hirshfeld analysis, molecular docking and DFT calculations of 5-Phenylamino-isophthalic acid: A good NLO material

Abstract

5-Phenylamino-isophthalic acid (H2L) (C15H13NO4) has been synthesized, characterized via single-crystal X-ray diffraction, spectroscopic techniques and also studied theoretically using DFT approach. The compound crystallizes in a monoclinic crystal system with a P21/c space group with Z = 2 and the following unit cell dimensions: a = 10.4415(14) Å, b = 16.472(2) Å, c = 7.5305(10) Å. DFT calculations were carried out by B3LYP/6–311++G(d,p) level and geometry optimization, vibrational analysis, MEP, ELF, NBO, NHO, and FMO analysis were also carried out. The calculated values showed excellent agreement with the experimental data. The vibrational frequencies were evaluated using density functional theory (DFT) with the complete PED analysis. The Molecular Frontiers Orbitals (FMO) or HOMO/LUMO energy values showed that there wasa satisfying interchange of charge occurring within the molecule. Hirshfeld surface analysis was carried out to study 3-D and 2-D interactions in crystal. Molecular docking was done with 4 protein receptors to find the best ligand-protein interactions. The nonlinear optical characteristics of the title compound have been evaluated using the Z-scan method with CW diode laser working at 520 nm. The third-order nonlinear refraction coefficient (n2), nonlinear absorption (β), nonlinear susceptibility χ(3), and second-order hyperpolarizability (γ) are of the order of 10−8 cm2/ W, 10−3 cm/ W, 10−7 esu, and 10−27 esu, respectively.