Abstract
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).
Highlights
Heterocycles are a class of chemical compounds in which one atom or more than one carboxyl group is replaced by a heteroatom such as oxygen, nitrogen, phosphorus or sulfur
As a continuation of our research devoted to the development of substituted 5-bromoindoline-2,3-dione derivatives, we report the synthesis and molecular and crystal structures, along with the Hirshfeld surface analysis and the density functional theory (DFT) computational calculations carried out at the B3LYP/6-311G(d,p) level, of a 5-bromoindoline-2,3-dione derivative by the alkylation reaction of 5-bromo-1H-indole-2,3-dione under phase-transfer catalysis conditions using tetra-n-butylammonium bromide (TBAB) as catalyst and potassium carbonate as base, leading to the title compound, (I)
The Hirshfeld surface analysis of the crystal structure indicates that the most important contributions for the crystal packing are from HÁ Á ÁH (28.1%), HÁ Á ÁO/OÁ Á ÁH (23.5%), HÁ Á ÁBr/BrÁ Á ÁH (13.8%), HÁ Á ÁCl/ClÁ Á ÁH (13.0%) and HÁ Á ÁC/CÁ Á ÁH (10.2%) interactions
Summary
Heterocycles are a class of chemical compounds in which one atom or more than one carboxyl group is replaced by a heteroatom such as oxygen, nitrogen, phosphorus or sulfur They are very interesting chemical compounds because of their potential applications in different fields. The first reports on the syntheses of isatin and isatin-based derivatives can be traced back to the first half of the 19th century, and almost one hundred years after those publications, the review ‘The Chemistry of Isatin’ showed the versatility of this molecular fragment. This reaction is used for the synthesis of natural. Hydrogen bonding and van der Waals interactions are the dominant interactions in the crystal packing
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