<p>2-((1-Phenyl-1<i>H</i>-1,2,3-triazol-4-yl)methoxy)benzonitrile (<b>3</b>), was synthesized by scaffold Schiff base condensation reaction of 1,2,3-triazole (<b>1</b>) and then followed by its dehydration. The title compound was characterized by typical spectroscopic techniques such as ¹H-NMR, ¹³C-NMR and FTIR. The structure of the title compound <b>3</b> was also determined by single crystal X-ray diffraction analysis. The compound co-crystallizes with water molecules, which occupy a twofold axis special position, in the orthorhombic system with space group Pnna and a = 13.606(3) Å, b = 23.442(5) Å, c = 8.2412(16) Å. The crystal structure is stabilized by strong hydrogen bonds between the water molecules and the compound, along with weaker secondary interactions, including π-π stacking and C-H···N interactions. The geometry of <b>3</b> was optimized by the DFT method and the results were compared with the single crystal X-ray diffraction data. Frontier molecular orbitals of the title compound <b>3</b> were calculated by using the B3LYP/6–31 + g(d,p) method. MEP analysis and Mulliken charge density, Global reactivity and thermodynamic properties were also performed.</p>