Synthesis, crystal structure and Hirshfeld surface analysis of 1-(12-bromododecyl)indoline-2,3-dione

Abstract

In the title compound, C20H28BrNO2, the indoline portion is almost planar and the 12-bromododecyl chain adopts an all-trans conformation apart from the gauche terminal C—C—C—Br fragment. A micellar-like structure is generated in the crystal by C—H...O hydrogen bonds and π-stacking interactions between indolinedione head groups and intercalation of the 12-bromododecyl tails. The Hirshfeld surface analysis of the crystal structure indicates that the most important contributions for the crystal packing are from H...H (58.9%), H...O/O...H (17.9%) and H...Br/Br...H (9.5%) contacts. A density functional theory (DFT) optimized structure at the B3LYP/ 6–311 G(d,p) level shows good agreement with the experimentally determined molecular structure in the solid state.

Crystal structure, Hirshfeld surface analysis, crystal voids, interaction energy calculations and energy frameworks, and DFT calculations of 1-(4-methylbenzyl)indoline-2,3-dione

“…Additionally, notable disparities were noted in the O1-C7-C8 bond angle (3.05 � ) and the C7-N1-C9-C10 torsion angle (0.85 � ). For instance, some reported bond lengths for O1-C7 and N1-C9 were fuond to vary by 0.03 and 0.01 A ˚, respectively, for 1-(12bromododecyl)indoline-2,3-dione (Rharmili et al, 2023a). These differences may be attributed to the fact that these calculations pertain to the isolated molecule, while the experimental results correspond to interacting molecules in the crystal lattice, where intra-and intermolecular interactions with neighbouring molecules are present.…”

“…Isatin derivatives have a biologically active heterocyclic moiety that comprises two cyclic rings, one of which is sixmembered and the other is five-membered (Rharmili et al, 2023a). Both the rings are planar.…”