Crystal structure, Hirshfeld surface analysis, crystal voids, inter-action energy calculations and energy frameworks, and DFT calculations of 1-(4-methyl-benz-yl)in-do-line-2,3-dione.

The in-do-line portion of the title mol-ecule, C16H13NO2, is planar. In the crystal, a layer structure is generated by C-H⋯O hydrogen bonds and C-H⋯π(ring), π-stacking and C=O⋯π(ring) inter-actions. The Hirshfeld surface analysis of the crystal structure indicates that the most important contributions for the crystal packing are from H⋯H (43.0%), H⋯C/C⋯H (25.0%) and H⋯O/O⋯H (22.8%) inter-actions. Hydrogen bonding and van der Waals inter-actions are the dominant inter-actions in the crystal packing. The volume of the crystal voids and the percentage of free space were calculated to be 120.52 Å3 and 9.64%, respectively, showing that there is no large cavity in the crystal packing. Evaluation of the electrostatic, dispersion and total energy frameworks indicate that the stabilization is dominated by the dispersion energy contributions in the title compound. Moreover, the DFT-optimized structure at the B3LYP/6-311G(d,p) level is compared with the experimentally determined mol-ecular structure in the solid state.

Synthesis, crystal structure and Hirshfeld surface analysis of 1-(12-bromo-dodec-yl)indoline-2,3-dione.

In the title compound, C20H28BrNO2, the indoline portion is almost planar and the 12-bromo-dodecyl 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 inter-actions between indolinedione head groups and inter-calation of the 12-bromo-dodecyl 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 mol-ecular structure in the solid state.

Crystal structure, Hirshfeld surface analysis and DFT studies of 5-bromo-1-{2-[2-(2-chloro-eth-oxy)eth-oxy]eth-yl}indoline-2,3-dione.

The title compound, C14H15BrClNO4, consists of a 5-bromo-indoline-2,3-dione unit linked to a 1-{2-[2-(2-chloro-eth-oxy)eth-oxy]eth-yl} moiety. In the crystal, a series of C-H⋯O hydrogen bonds link the molecules to form a supramolecular three-dimensional structure, enclosing R 2 2(8), R 2 2(12), R 2 2(18) and R 2 2(22) ring motifs. π-π contacts between the five-membered dione rings may further stabilize the structure, with a centroid-centroid distance of 3.899 (2) Å. The Hirshfeld surface analysis of the crystal structure indicates that the most important contributions for the crystal packing are from H⋯H (28.1%), H⋯O/O⋯H (23.5%), H⋯Br/Br⋯H (13.8%), H⋯Cl/Cl⋯H (13.0%) and H⋯C/C⋯H (10.2%) inter-actions. Hydrogen bonding and van der Waals inter-actions are the dominant inter-actions in the crystal packing. Density functional theory (DFT) optimized structures at the B3LYP/6-311G(d,p) level are compared with the experimentally determined mol-ecular structure in the solid state. The HOMO-LUMO behaviour was elucidated to determine the energy gap. The chloro-eth-oxy-ethoxyethyl side chain atoms are disordered over two sets of sites with an occupancy ratio of 0.665 (8):0.335 (6).