X-ray and DFT calculated structures of 2-(1H-imidazol-1-yl)-1-(2-naphthyl)ethan-1-one N-phenylthiosemicarbazone and 2-(1H-imidazol-1-yl)-1-(2-naphthyl)ethan-1-one N-(4-chlorophenyl)thiosemicarbazone

Crystal and molecular structures of two new compounds 2-(1 H -imidazol-1-yl)-1-(2-naphthyl)ethan-1-one N -phenylthiosemicarbazone, C 22 H 19 N 5 S, ( I ) and 2-(1 H -imidazol-1-yl)-1-(2-naphthyl)ethan-1-one N -(4-chlorophenyl)thiosemicarbazone, C 22 H 18 ClN 5 S, ( II ) have been determined by single-crystal X-ray diffraction. Molecular geometries from X-ray experiment of I and II have been compared with those calculated using the Density Functional Theory (DFT) with B3LYP/6-31G( d , p ) basis set. Both compounds crystallize in the monoclinic space group P 2 1 / c with Z = 4: a = 13.2880(5), 14.2648(3) Å, b = 9.4122(2), 9.3892(3) Å, c = 15.6341(6), 15.6268(4) Å, β = 101.779(3)°, 104.926(2)°, for I and II , respectively. An extensive two-dimensional network of N-H⋯N hydrogen bonds and π-ring interactions are responsible for crystal stabilization in both structures.