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6902005 
Journal Article 
6-Chloro-2-oxindole: X-ray and DFT-calculated study 
Hachula, B; Zerzucha, P; Zubko, M; Kusz, J; , 
2011 
Yes 
Acta Crystallographica. Section C: Crystal Structure Communications
ISSN: 0108-2701 
WILEY-BLACKWELL 
HOBOKEN 
O413-O416 
21979979 
WOS:000295576800016 
The molecule of the title compound (systematic name: 6-chloroindolin-2-one), C8H6ClNO, is almost planar, with a dihedral angle of 1.13 (9)degrees between the planes of the constituent pyrrolidine and benzene rings. Centrosymmetric dimers are formed in the crystal structure by N-H center dot center dot center dot O hydrogen bonds, and these dimers are additionally linked by Cl center dot center dot center dot Cl and C-H center dot center dot center dot O interactions. Density functional theory (DFT) calculations at the B3LYP/6-31 G(d,p) level of theory were used to optimize the molecular structure and the geometry was best reproduced by optimization of two interacting molecules. The bond orders in the molecule, estimated using the natural bond orbitals (NBO) formalism, are consistent with the observed bond lengths. In particular, the contribution of the lone pair of electrons on the N atom to the N-C bond in the N-C=O group is revealed. The measured IR spectrum of the compound shows a red shift of the N-H stretching frequency compared with the free molecule, due to the formation of the hydrogen bonds.