Mohammed Hadj Mortada Belhachemi1, Nourdine Boukabcha1,
Zohra Douaa Benyahlou1, Abdelkader Chouaih1
1Laboratory of Technology and Solid Properties (LTSP), Abdelhamid Ibn Badis University of Mostaganem, 27000 Mostaganem, Algeria
Organic compounds have special properties due to the versatility of the carbon atom, which can engage in various types of bonding either between carbon atoms or with atoms of other elements. Among organic compounds, isatin also called indoline-2, 3-dione, is a bicyclic and heterocyclic aromatic organic molecule. The crystals of isatin are part of the centrosymmetric group. In the current study, 1-(4-fluorobenzyl)-5-bromolindolin-2,3-dione (FBID) has been synthesized and characterized by single-crystal X-ray diffraction (XRD) . This compound crystallized in an orthorhombic system with a space group P212121. Theoretical calculations were carried out using the DFT method using B3LYP function with 6-311G(d,p) basis set, in order to compare and complement the experimental results of structural geometry, demonstrating a very good correspondence between them. the torsion angles results confirm that compound doesn’t have a planar structure. Moreover, the hirshfeld surface analysis and 2D-fingerprint plots have indicated that H⋯O/O⋯H (20.9%), H⋯F/F⋯H (18.9%), H⋯C/C⋯H (17%), H⋯H, C⋯C (10.6%) and H⋯Br/Br⋯H (9.4%) contacts were the most important contributors among the interacting atoms which stabilized the crystal structure. Reduced density gradient (RDG) was devoted to analyse weak and strong attraction interactions and even steric repulsions within the molecule. Therefore, the RDG result of the compound corresponds well with the results of the hirshfeld surface analysis. Finally, molecular docking has been applied, indicating favourable performance and good binding affinity between FBID molecule and the target protein.
Keywords: heterocycle; XRD; crystal; isatin; H-Bond