Experimental and computational studies on the synthesis and structural characterization of 2-(4-chlorophenoxy)-N-[4-(4-methylphenyl)-1,3-thiazol-2-yl]acetamide

• Novel thiazol acetamide derivative is synthesized and spectroscopically characterized. • XRD study confirms the compound structure and reveals that it crystallizes in orthorhombic crystal system. • Crystal structure is stabilized by C-H...O intermolecular and CH...N intramolecular hydrogen bond interactions. • DFT computations, Hirshfeld surface studies, and Energy frameworks analysis are performed. • The energy gap (4.569 eV) between HOMO-LUMO implies the stability of the thiazol acetamide compound. The title compound 2-(4-chlorophenoxy)- N -[4-(4-methylphenyl)-1,3-thiazol-2-yl]acetamide (3) has been achieved via a sequence of multistep synthesis processes in good yield started by 2-(4-chlorophenoxy)acetic acid (1) with 4-(4-methylphenyl)thiazol-2-amine (2) in dry dichloromethane followed by the addition of lutidine, and O -(benzotriazole-1-yl)- N,N,N',N' -tetramethyluroniumtetrafluoroborate as coupling agent in cold condition to accomplish (3) . The synthesized compound was elucidated by different spectroscopic techniques (NMR and LC-MS) and finally, the structure was confirmed by X-ray diffraction method. The title compound has crystallized in the orthorhombic crystal system with the space group Pca2 1 . Density functional theory calculations were carried out to compare the computational values of (1) and (2) with (3) . The frontier molecular orbitals (HOMO-LUMO) and molecular electrostatic potential (MEP) of (3) were analyzed. In the crystal structure, intermolecular and intramolecular interactions were observed. Atom N12 represents the chiral center of (3) which is connected to four different groups. The stereochemistry of this molecule at N12 is S configuration. Hirshfeld surface studies and 2D fingerprint plots neatly quantify the interactions involved within the structure. Energy frameworks analysis for (3) were performed through different intermolecular interaction energies to understand the packing of molecules and to determine the type of the dominant energy.