Synthesis, crystal structure and spectroscopic and Hirshfeld surface analysis of 4-hydroxy-3-methoxy-5-nitrobenzaldehyde

Abstract

The title compound, C8H7NO5, is planar with an r.m.s. deviation for all non-hydrogen atoms of 0.018 Å. An intramolecular O—H...O hydrogen bond involving the adjacent hydroxy and nitro groups forms an S(6) ring motif. In the crystal, molecules are linked by O—H...O hydrogen bonds, forming chains propagating along the b-axis direction. The chains are linked by C—H...O hydrogen bonds, forming layers parallel to the bc plane. The layers are linked by a further C—H...O hydrogen bond, forming slabs, which are linked by C=O...π interactions, forming a three-dimensional supramolecular structure. Hirshfeld surface analysis was used to investigate intermolecular interactions in the solid state. The molecule was also characterized spectroscopically and its thermal stability investigated by differential scanning calorimetry and by thermogravimetric analysis.

Crystal structure and Hirshfeld surface analysis of 4-allyl-2-methoxy-6-nitrophenol

“…4-allyl-2methoxy-5-nitrophenyl acetate (refcode: TEJREG; Carrasco-Altamirano et al, 2006) and 4-hydroxy-3-methoxy-5-nitroacetophenone (5-nitroapocynin) (MUCDOE; Babu et al, 2009). A third related compound, 4-hydroxy-3-methoxy-5nitrobenzaldehyde, has recently been reported (Vusak et al, 2020). All of these compounds exhibit intramolecular hydrogen bonds involving the nitro O atoms with the H atoms of the hydroxide group, and other intermolecular hydrogen bonds, in addition tointeractions, which assure the crystal cohesion.…”