1-Ethyl-5-iodoindoline-2,3-dione

Abstract

There are two independent mol­ecules in the asymmetric unit of the title compound, C10H8INO2, which differ in the degree of planarity. The iodo­indoline-2,3-dione skeleton of mol­ecule 1 is essentially planar [mean deviation = 0.003 (2) Å for the nine non-H atoms of the indoline core, with a maximum deviation of 0.033 (1) Å for the I atom]. The I atom and O atom in the 3-position of mol­ecule 2 deviate by 0.195 (1) and 0.120 (2) Å, respectively, from the least-squares plane through the nine non-H atoms of the indoline core. Mol­ecules 1 and 2 are roughly coplanar, the mean planes through their cores making a dihedral angle of 6.84 (1)°. This coplanarity results in a layer-like structure parallel to (6,11,17) in the crystal, the distance between adjacent least-squares planes through the cores of mol­ecules 1 and 2 being 3.37 (1) Å. In such a layer, mol­ecules 1 and 2 are linked by C—H⋯O hydrogen bonds, forming chains along [11-1]. The chains are further coupled to construct a kind of double-chain structure via I⋯O inter­actions [3.270 (2) Å].

4-Iodo-1H-indole-2,3-dione

“…The dimers are further linked into zigzag chains along [010] by pairs of weak IÁ Á ÁO interactions [I1Á Á ÁO2 i = 3.184 (4) Å ; symmetry code (i): Àx + 2, Ày + 1, Àz + 1]. Similar IÁ Á ÁO interactions have been observed in 5-iodoisatin and its derivatives (Abid et al, 2008;Garden et al, 2006;Wang et al, 2014). The closely related 4-bromoisatin also exhibits a weak halogen-oxygen interaction in the solid state (Huang et al, 2016).…”

Crystal structure of 1-ethyl-5-iodoindolin-2-one

“…precursor (Wang et al,2014). On the other hand, the noncentrosymmetry of the title crystal may be better explained by the IÁ Á ÁI intermolecular interactions, for there are no IÁ Á ÁI short contacts in the above centrosymmetric precursor crystal.…”

6-Chloro-1-phenylindoline-2,3-dione: absolute structure, non-linear optical and charge-transport properties

“…The crystal structures of many isatin derivatives have been reported, among the analogues of the title compound are 6-bromo-1-butylindoline-2,3-dione (Ji et al, 2009), 1-ethyl-5iodoindoline-2,3-dione (Wang et al, 2014), 6-chloroindoline-2,3-dione (Golen & Manke, 2016), 1-benzyl-5-fluoroindoline-2,3-dione (Sharmila et al, 2015) and 1-phenylindoline-2,3dione (Shukla & Rajeswaran, 2011). The synthesis of the title compound was reported in 2014 (Bergman & Stensland, 2014).…”