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

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 center dot center dot center dot O (2.738-2.874 & Aring;) 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 center dot center dot center dot H, O center dot center dot center dot H/H center dot center dot center dot O, C center dot center dot center dot H/H center dot center dot center dot C and Br center dot center dot center dot H/H center dot center dot center dot 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).