Study of 5-azidomethyl-8-hydroxyquinoline structure by X-ray diffraction and HF-DFT computational methods.

5-Azidomethyl-8-hydroxyquinoline has been synthesized and characterized using IR, H and C NMR spectroscopic methods. Thermal analysis revealed no solid-solid phase transitions. The crystal structure of this compound was refined by Rietveld method from powder X-ray diffraction data at 295 K. The single- crystal structure of the compound at 260 K was solved and refined using SHELX 97 program. According to the data obtained by both methods, the structure of the compound is monoclinic, space group P2/ c, with Z = 4 and Z' = 1. For the single crystal at 260 K, a = 12.2879 (9) Å, b = 4.8782 (3) Å, c = 15.7423 (12) Å, β=100.807(14)°. Mechanisms of deformation resulting from intra- and intermolecular interactions, such as hydrogen bonding, induced slight torsions in the crystal structure. The optimized molecular geometry of 5-azidomethyl-8-hydroxyquinoline in the ground state is calculated using density functional theory (B3LYP) and Hartree-Fock (HF) methods with the 6-311G( d,p) basis set. The calculated results show good agreement with experimental values. Energy gap of the molecule was found using HOMO and LUMO calculation which reveals that charge transfer occurs within the molecule. [ABSTRACT FROM AUTHOR]