Synthesis, structural studies and Hirshfeld surface analysis of the substituted isoindole-1,3‑dione derivatives

•The regioselective ring opening reaction of 5-benzyl/ethyl-2-hydroxyhexahydro-4H-oxireno[2,3-e]isoindole-4,6(5H)‑dione with HBr was examined.•5‑bromo-2-benzyl/ethyl-4,6-dihydroxyhexahydro-1H-isoindole 1,3(2H)‑dione was determined by X-ray diffraction analysis.•X-Ray analysis of the compounds showed that the group attached to the nitrogen atom in the five-membered imide ring affected the crystal structure of the molecule.•Hirshfeld surface analyzes of compounds provided information about the molecular, crystal structure and intermolecular interactions.•To better understand the packing of the crystal structure and the intermolecular rearrangements into the structures, the energy frameworks were analyzed. In this study, we have performed the ring-opening reaction of 5-benzyl/ethyl-2-hydroxyhexahydro-4H-oxireno[2,3-e] isoindole-4,6(5H)‑dione (10) with HBr to the corresponding bromodiols, regioselectively. Structures of the synthesized compounds are elucidated through spectral methods (1H NMR,13C NMR and HRMS) Afterwards, the racemic products 11a-b were purified and the absolute geometries of 5‑bromo-2-ethyl-4,6-dihydroxyhexahydro-1H-isoindole 1,3(2H)‑dione (11a) and 2-benzyl-5‑bromo-4,6-dihydroxyhexahydro-1H-isoindole-1,3(2H)‑dione (11b) was determined by X-ray diffraction analysis. Effective O−H∙∙∙O (2.738–2.874 Å) hydrogen bonds between diol and ketone units are important interactions between the molecules. Hirshfeld surface analyses of the compounds (11a-b) have provided further insights into molecular, crystal structure and intermolecular interactions. The results indicated that the most important contributions for the crystal packings are from H∙∙∙H, O∙∙∙H/H∙∙∙O, C∙∙∙H/H∙∙∙C and Br∙∙∙H/H∙∙∙Br interactions. Finally, energy frameworks were analyzed to a better understanding of the packing of crystal structure and the supramolecular rearrangements for the structures (11a-b). [Display omitted]