Crystal structure, Hirshfeld surfaces and DFT computation of NLO active (2E)-2-(ethoxycarbonyl)-3-[(1-methoxy-1-oxo-3-phenylpropan-2-yl)amino] prop-2-enoic acid

• NLO active (2E)-2- (ethoxycarbonyl)-3-[(1-methoxy-1-oxo-3-phenylpropan-2-yl)amino]prop-2-enoic acid is synthesized.
• The compound crystallizes in non-centrosymmetric space group P21.
• Crystal structure is analyzed.
• The SHG efficiency of the compound displays 8 fold excess when compared with standard KDP.
• Intermolecular interactions are analyzed using Hirshfeld surfaces.
• The energetics of molecular pairs is estimated using PIXEL method.
• Mulliken atomic charges, polarizability, hyperpolarizability and molecular electrostatic potential are calculated.

Nonlinear optical (NLO) activity of the compound (2E)-2-(ethoxycarbonyl)-3-[(1-methoxy-1-oxo-3-phenylpropan-2-yl)amino] prop-2-enoic acid is investigated experimentally and theoretically using X-ray crystallography and quantum chemical calculations. The NLO activity is confirmed by both powder Second Harmonic Generation (SHG) experiment and first hyper polarizability calculation. The title compound displays 8 fold excess of SHG activity when compared with the standard compound KDP. The gas phase geometry optimization and vibrational frequencies calculations are performed using density functional theory (DFT) incorporated in B3LYP with 6–311G++(d,p) basis set. The title compound crystallizes in non–centrosymmetric space group P21. Moreover, the crystal structure is primarily stabilized through intramolecular N–H···O and O–H···O hydrogen bonds and intermolecular C–H···O and C–H···π interactions. These intermolecular interactions are analyzed and quantified using Hirshfeld surface analysis and PIXEL method. The detailed vibrational assignments are performed on the basis of the potential energy distributions (PED) of the vibrational modes.

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