1-Ethyl-5-iodo­indoline-2,3-dione

Lei Wang; Yu-Xiang Shen; Jian-Tong Dong; Man Zhang; Qi Fang

doi:10.1107/S1600536813033539

. 2013 Dec 14;70(Pt 1):o67. doi: 10.1107/S1600536813033539

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

Lei Wang ^a, Yu-Xiang Shen ^b, Jian-Tong Dong ^a, Man Zhang ^a, Qi Fang ^b,^*

PMCID: PMC3914098 PMID: 24527003

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].

Related literature

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 ▶). graphic file with name e-70-00o67-scheme1.jpg

Experimental

Crystal data

C₁₀H₈INO₂
M _r = 301.07
Triclinic,
a = 9.9658 (2) Å
b = 10.1453 (2) Å
c = 11.3007 (2) Å
α = 71.188 (1)°
β = 72.599 (1)°
γ = 84.434 (1)°
V = 1032.04 (3) Å³
Z = 4
Mo Kα radiation
μ = 3.08 mm⁻¹
T = 295 K
0.27 × 0.21 × 0.10 mm

Data collection

Bruker APEXII CCD diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2005 ▶) T _min = 0.490, T _max = 0.746
13515 measured reflections
5091 independent reflections
4358 reflections with I > 2σ(I)
R _int = 0.017

Refinement

R[F ² > 2σ(F ²)] = 0.023
wR(F ²) = 0.066
S = 1.01
5091 reflections
279 parameters
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.74 e Å⁻³
Δρ_min = −0.44 e Å⁻³

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 Material

Crystal structure: contains datablock(s) I, global. DOI: 10.1107/S1600536813033539/vm2202sup1.cif

e-70-00o67-sup1.cif^{(26.9KB, cif)}

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536813033539/vm2202Isup2.hkl

e-70-00o67-Isup2.hkl^{(249.3KB, hkl)}

Click here for additional data file.^{(3.6KB, cml)}

Supporting information file. DOI: 10.1107/S1600536813033539/vm2202Isup3.cml

Additional supporting information: crystallographic information; 3D view; checkCIF report

Table 1. Hydrogen-bond geometry (Å, °).

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C29—H29A⋯O2ⁱ	0.97	2.57	3.399 (3)	144
C27—H27⋯O2ⁱ	0.93 (3)	2.48 (3)	3.407 (3)	174 (3)
C9—H9A⋯O4	0.97	2.56	3.366 (3)	140

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Symmetry code: (i) Inline graphic .

Acknowledgments

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.

supplementary crystallographic information

1. Comment

To date, isatin and its derivatives have received much attention due to their potential applications in biomedicine and agrochemical industries (Silva et al., 2001). In this paper, we report the synthesis and structure of a new isatin derivative, namely 1-ethyl-5-iodoindoline-2,3-dione.

There are two molecules in the asymmetric unit of the unit cell as depicted in Fig. 1. The two molecules are essentially planar. All non-hydrogen atoms, except the terminal methyl C atom, are in a same plane. The iodoindoline-2,3-dione skeleton of molecule 1 has a perfect planarity (mean deviation is 0.003 (2) Å, maximum deviation is 0.033 (1) Å for I1 for the least-squares plane through the 9 non-hydrogen atoms of the indoline core). In molecule 2, two large deviations exist [0.195 (1) (I2) and 0.120 (2) Å (O3)], and the mean deviation is relatively larger [0.022 (2) Å]. Molecules 1 and 2 are virtually co-planar with a small dihedral angle of 6.84 (1) ° between both best planes. This co-planarity results in a layer-like structure of the crystal (Figs. 2 and 3). Considering this co-planarity, the least-squares plane through the 18 non-hydrogen atoms of the two indoline cores of the two molecules shows a mean deviation of 0.064 (3) Å. The distance between two such adjacent best planes or layers is 3.37 (1) Å.

Several intermolecular interactions can be found in a layer. The C—H···O hydrogen bonds (Table 1) help to build one-dimensional chains and the I1···O3 [-x, 1 - y, 1 - z] [3.270 (2) Å] short contact helps to construct a kind of double-chain structure.

2. Experimental

We synthesized the title compound by the similar method reported by Ji et al. (2010). KI (1.27 g), hexadecyl trimethyl ammonium bromide (0.410 g) and 5-iodoisatin (3.75 g) were dissolved in 20 ml DMSO, and the mixture was stirred in N₂ atmosphere while 2.7 ml iodoethane was quickly added via a syringe. Then 5 ml aqueous KOH solution (17.8 mol/L) was dropwise added into the brown solution at 30 °C and the colour rapidly became black. After another 3 ml iodoethane was added, the heating temperature was raised to 45 °C. The mixture was stirred for 5 h, then 1.6 ml iodoethane was added. The reaction continued for 1 h at 45°C. The mixture was then poured into water, and extracted with dichloromethane. The organic phase was seperated and dried over anhydrous Na₂SO₄. The solvent was evaporated under reduced pressure, the crude product was purified by column chromatography [V (dichloromethane)/ V (petroleum ether) = 1:1] obtaining 47.4% yield. Crystals suitable for X-ray diffraction were obtained by slow evaporation of a dichloromethane solution of the compound.