X–N charge density analysis of the hydrogen bonding motif in 1-(2-hydroxy-5-nitrophenyl)ethanone

Abstract

The total experimental charge density in 1-(2-hydroxy-5-nitrophenyl)ethanone (1) has been determined using high-resolution X-ray diffraction data in combination with neutron diffraction data measured at 100 K. Multipole refinement was carried out in terms of the rigid pseudoatom model. Multipole refinement converged at R = 0.026 for 5415 reflections with I > 2σ(I). Topological analysis of the total experimental charge density p(r) and its Laplacian, -∇2ρ(r) together with a comparison against high level theoretical gas-phase calculations reveals fine details of intra- intermolecular bonding features, in particular the extent of the π-delocalisation throughout the molecule. © Royal Society of Chemistry 2025.