Crystal structure, Hirshfeld surface analysis and DFT studies of 2-[(2-hy-droxy-5-methyl-benzyl-idene)amino]-benzo-nitrile.

ABSTRACT: The title compound, C15H12N2O, was synthesized by condensation reaction of 2-hy-droxy-5-methyl-benzaldehyde and 2-amino-benzo-nitrile, and crystallizes in the ortho-rhom-bic space group Pbca. The phenol ring is inclined to the benzo-nitrile ring by 25.65?(3)°. The configuration about the C=N bond is E, stabilized by a strong intra-molecular O-H?N hydrogen bond that forms an S(6) ring motif. In the crystal, C-H?O and C-H?N inter-actions lead to the formation of sheets perpendicular to the a axis. C-H?? inter-actions, forming polymeric chains along the a-axis direction, connect these sheets into a three-dimensional network. A Hirshfeld surface analysis indicates that the most important contributions for the packing arrangement are from H?H and C?H/H?C inter-actions. The density functional theory (DFT) optimized structure at the B3LYP/6-311?G(d,p) level is compared with the experimentally determined mol-ecular structure and the HOMO-LUMO energy gap is given.

SUBMITTER: Faizi MSH 

PROVIDER: S-EPMC7405566 | biostudies-literature | 2020 Aug

REPOSITORIES: biostudies-literature