(Graph Presented). The aromatic C-H⋯O hydrogen bonding within the series of the structurally relative indenone derivatives has been studied. The presence of the hydrogen bonds is corroborated by the large low-field chemical shifts of the protons involved in the hydrogen bond observed experimentally and reproduced by quantum mechanical calculations. Further confirmation is provided by analysis of the orbital overlap coefficients, 13C NMR chemical shifts, and one-bond spin-spin coupling constants J(13C- 1H). The relationship between molecular geometry and 1H NMR chemical shifts of involved protons has a complex nature, but the C-H⋯O distance is the principal factor.