Synthesis, crystal structure, spectral analysis and DFT computational studies on a novel isoindoline derivative

• The novel isoindoline single crystals have been synthesized.
• The crystal system was characterized by FT-IR and UV–Vis studies.
• The molecular geometry and vibrational frequencies are calculated using DFT.
• NLO, FMO and MEP analysis of the compound were studied.

The isoindoline compound, 2-(3-chloro-4-(4-chlorophenoxy)phenyl)isoindoline-1,3-dione, has been synthesized and characterized by FT-IR, UV–Vis and X-ray single-crystal determination. The compound crystallizes in the monoclinic space group P21/c with a = 20.441 (3) Å, b = 4.0258 (4) Å, c = 23.836 (2) Å, β = 121.918 (7)° and Z = 4. The molecular structure and vibrational frequencies in the ground state were calculated using the density functional theory method (B3LYP) with 6-311++G(d,p) basis set. The results obtained from the optimization and vibrational analyses are agree with the experimental results. Using the TD-DFT method, electronic absorption spectra have been calculated, and they are compatible with the experimental ones. The electric dipole moment (μ), polarizability (α) and the first hyperpolarizability (β) values of the compound were calculated theoretically. The first hyperpolarizability of the molecule shows that the compound can be a good candidate of nonlinear optical material. In addition, DFT calculations of the compound, atomic charges, molecular electrostatic potential and thermodynamic properties were also performed at B3LYP/6-311++G(d,p) level of theory.

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