Received 6 December 2013
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-HO hydrogen bonds, forming chains along [11-1]. The chains are further coupled to construct a kind of double-chain structure via IO interactions [3.270 (2) Å].
For applications of indoline-2,3-dione in drug design, see: Silva et al. (2001). For the synthesis of the title compound, see: Ji et al. (2010). For related structures, see: Garden et al. (2006); Abid et al. (2008); Kurkin et al. (2008).
Data collection: APEX2 (Bruker, 2005); cell refinement: SAINT (Bruker, 2005); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008) and Mercury (Macrae et al., 2006); software used to prepare material for publication: SHELXL97.
Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: VM2202 ).
This work was supported by the National Natural Science Foundation of China (grant No. 20972089) and by a grant from the State Key Laboratory of Crystal Materials.
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