Crystal Structure and Quantum Chemical Calculations on o-Hydroxyacetophenone Phenylhydrazone

o-Hydroxyacetophenone phenylhydrazone has been synthesized and characterized by elemental analysis, IR and electronic spectroscopy. The X-ray crystal structure study shows that the compound contains two crystallographically independent molecules in the asymmetric unit and crystallizes in the monoclinic system, space group P21/c, with Mr =226.27 (C14H14N2O), a = 13.433(3), b = 10.738(2), c = 18.351(7) Capital A, beta = 114.44(2)°, V = 2409.8(12) Capital A 3, Z = 8, Dc = 1.247 Mg/m3, F (000) = 960, mi (Mo K) = 0.080 mm–1, R = 0.0638, wR = 0.1535. Ab initio calculations of the structure, atomic charge distributions, natural bond orbital analysis and thermodynamic functions of the title compound were performed at HF/6-311G** and B3LYP/6-311G** levels of theory. Electronic absorption spectra were calculated by the time-dependent density functional theory (TD-DFT). Vibrational frequencies were predicted, as signed and compared with the experimental values. The calculation of the second order optical nonlinearity was carried out and the molecular hyperpolarizability of 3.332×10–30 esu was predicted.