Two new compounds, 1-(3-morpholinopropyl)-3-(4-chlorobenzoyl)thiourea monohydrate (I) and 1-(3-morpholinopropyl)-3-(4-methylbenzoyl)thiourea monohydrate (II) have been synthesized and characterized by FT-IR, H-1 NMR, C-13 NMR, and Single-Crystal X-Ray Diffraction analyses. Theoretical investigations have been calculated by using DFT method of B3LYP/6-31G + (2d, p) and B3LYP/6-311G + (2d, p) basis sets. Each compound contains a water molecule, forming intra and intermolecular hydrogen bonds with other molecules and further stabilizes the crystal structure. Theoretical calculations of bond parameters, harmonic vibration frequencies, and isotropic chemical shifts are in good agreement with the experimental results. The observed intermolecular interactions in the crystal packing are the main cause of the calculated torsion angles, molecular vibrations, and chemical shifts. The calculated molecular vibrations show good correlation values ranging from 0.995, 0.996, and 0.997 with the experimental data, where the higher basis set fits the experimental results better.