1-(Morpholinomethyl)indoline-2,3-dione

The title compound, C14H15BrClNO4, consists of a 5-bromoindoline-2,3-dione unit linked to a 1-{2-[2-(2-chloroethoxy)ethoxy]ethyl} 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%) interactions. Hydrogen bonding and van der Waals interactions are the dominant interactions in the crystal packing. Density functional theory (DFT) optimized structures at the B3LYP/6-311G(d,p) level are compared with the experimentally determined molecular structure in the solid state. The HOMO—LUMO behaviour was elucidated to determine the energy gap. The chloroethoxyethoxyethyl side chain atoms are disordered over two sets of sites with an occupancy ratio of 0.665 (8):0.335 (6).

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Crystal structure, Hirshfeld surface analysis and DFT studies of 5-bromo-1-{2-[2-(2-chloroethoxy)ethoxy]ethyl}indoline-2,3-dione

Abdellaoui¹,

Hökelek

Capet

et al. 2019

Acta Cryst E

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1-(Morpholinomethyl)indoline-2,3-dione

Abstract: In the title compound, C13H14N2O3, the morpholine ring displays a chair conformation, with the (2,3-dioxoindolin-1-yl)methyl group in an equatorial position. The crystal structure is stabilized by intermolecular C—H⋯O hydrogen bonds.

Cited by 1 publication

References 5 publications

Crystal structure, Hirshfeld surface analysis and DFT studies of 5-bromo-1-{2-[2-(2-chloroethoxy)ethoxy]ethyl}indoline-2,3-dione

Crystal structure, Hirshfeld surface analysis and DFT studies of 5-bromo-1-{2-[2-(2-chloroethoxy)ethoxy]ethyl}indoline-2,3-dione

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1-(Morpholinomethyl)indoline-2,3-dione

Abstract: In the title compound, C13H14N2O3, the morpholine ring displays a chair conformation, with the (2,3-dioxoindolin-1-yl)methyl group in an equatorial position. The crystal structure is stabilized by inter­molecular C—H⋯O hydrogen bonds.

Cited by 1 publication

References 5 publications

Crystal structure, Hirshfeld surface analysis and DFT studies of 5-bromo-1-{2-[2-(2-chloroethoxy)ethoxy]ethyl}indoline-2,3-dione

Crystal structure, Hirshfeld surface analysis and DFT studies of 5-bromo-1-{2-[2-(2-chloroethoxy)ethoxy]ethyl}indoline-2,3-dione

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Abstract: In the title compound, C13H14N2O3, the morpholine ring displays a chair conformation, with the (2,3-dioxoindolin-1-yl)methyl group in an equatorial position. The crystal structure is stabilized by intermolecular C—H⋯O hydrogen bonds.