Crystal structure, Hirshfeld surface analysis and inter-action energy and DFT studies of 2-(2,3-di-hydro-1H-perimidin-2-yl)-6-meth-oxy-phenol.

ABSTRACT: The title compound, C18H16N2O2, consists of perimidine and meth-oxy-phenol units, where the tricyclic perimidine unit contains a naphthalene ring system and a non-planar C4N2 ring adopting an envelope conformation with the NCN group hinged by 47.44?(7)° with respect to the best plane of the other five atoms. In the crystal, O-HPhnl?NPrmdn and N-HPrmdn?OPhnl (Phnl = phenol and Prmdn = perimidine) hydrogen bonds link the mol-ecules into infinite chains along the b-axis direction. Weak C-H?? inter-actions may further stabilize the crystal structure. The Hirshfeld surface analysis of the crystal structure indicates that the most important contributions for the crystal packing are from H?H (49.0%), H?C/C?H (35.8%) and H?O/O?H (12.0%) inter-actions. Hydrogen bonding and van der Waals inter-actions are the dominant inter-actions in the crystal packing. Computational chemistry indicates that in the crystal, the O-HPhnl?NPrmdn and N-HPrmdn?OPhnl hydrogen-bond energies are 58.4 and 38.0?kJ?mol-1, respectively. Density functional theory (DFT) optimized structures at the B3LYP/ 6-311?G(d,p) level are compared with the experimentally determined mol-ecular structure in the solid state. The HOMO-LUMO behaviour was elucidated to determine the energy gap.

SUBMITTER: Daouda B 

PROVIDER: S-EPMC7199263 | biostudies-literature | 2020 May

REPOSITORIES: biostudies-literature