6‐Chloro‐2‐oxindole: X‐ray and DFT‐calculated study
Authors: Hachuła, Barbara; Zerzucha, Piotr; Zubko, Maciej; Kusz, Joachim
Source: Acta Crystallographica Section C, Volume 67, Number 10, 15 October 2011 , pp. o413-o416(4)
Abstract:The molecule of the title compound (systematic name: 6‐chloroindolin‐2‐one), C8H6ClNO, is almost planar, with a dihedral angle of 1.13 (9)° between the planes of the constituent pyrrolidine and benzene rings. Centrosymmetric dimers are formed in the crystal structure by N—H...O hydrogen bonds, and these dimers are additionally linked by Cl...Cl and C—H...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.
Document Type: Research Article
Publication date: October 15, 2011