[Journal logo]

Volume 70 
Part 1 
Page o67  
January 2014  

Received 6 December 2013
Accepted 11 December 2013
Online 14 December 2013

Key indicators
Single-crystal X-ray study
T = 295 K
Mean [sigma](C-C) = 0.004 Å
R = 0.023
wR = 0.066
Data-to-parameter ratio = 18.2
Details
Open access

1-Ethyl-5-iodo­indoline-2,3-dione

aSchool of Chemistry and Chemical Engineering, Shandong University, Jinan 250100, People's Republic of China, and bState Key Laboratory of Crystal Materials, Shandong University, Jinan 250100, People's Republic of China
Correspondence e-mail: fangqi@sdu.edu.cn

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[Silva, J. F., Garden, S. J. & Pinto, A. C. (2001). J. Braz. Chem. Soc. 12, 273-324.]). For the synthesis of the title compound, see: Ji et al. (2010[Ji, L., Fang, Q., Yuan, M. S., Liu, Z. Q., Shen, Y. X. & Chen, H. F. (2010). Org. Lett. 12, 5192-5195.]). For related structures, see: Garden et al. (2006[Garden, S. J., Pinto, A. C., Wardell, J. L., Low, J. N. & Glidewell, C. (2006). Acta Cryst. C62, o321-o323.]); Abid et al. (2008[Abid, O.-R., Qadeer, G., Rama, N. H. & Ruzicka, A. (2008). Acta Cryst. E64, o2223.]); Kurkin et al. (2008[Kurkin, A. V., Bernovskaya, A. A., Yurovskaya, M. A. & Rybakov, V. B. (2008). Acta Cryst. E64, o1448.]).

[Scheme 1]

Experimental

Crystal data
  • C10H8INO2

  • Mr = 301.07

  • Triclinic, [P \overline 1]

  • a = 9.9658 (2) Å

  • b = 10.1453 (2) Å

  • c = 11.3007 (2) Å

  • [alpha] = 71.188 (1)°

  • [beta] = 72.599 (1)°

  • [gamma] = 84.434 (1)°

  • V = 1032.04 (3) Å3

  • Z = 4

  • Mo K[alpha] radiation

  • [mu] = 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[Bruker (2005). APEX2, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.]) Tmin = 0.490, Tmax = 0.746

  • 13515 measured reflections

  • 5091 independent reflections

  • 4358 reflections with I > 2[sigma](I)

  • Rint = 0.017

Refinement
  • R[F2 > 2[sigma](F2)] = 0.023

  • wR(F2) = 0.066

  • S = 1.01

  • 5091 reflections

  • 279 parameters

  • H atoms treated by a mixture of independent and constrained refinement

  • [Delta][rho]max = 0.74 e Å-3

  • [Delta][rho]min = -0.44 e Å-3

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
Symmetry code: (i) x+1, y+1, z-1.

Data collection: APEX2 (Bruker, 2005[Bruker (2005). APEX2, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.]); cell refinement: SAINT (Bruker, 2005[Bruker (2005). APEX2, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.]); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); molecular graphics: SHELXTL (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]) and Mercury (Macrae et al., 2006[Macrae, C. F., Edgington, P. R., McCabe, P., Pidcock, E., Shields, G. P., Taylor, R., Towler, M. & van de Streek, J. (2006). J. Appl. Cryst. 39, 453-457.]); software used to prepare material for publication: SHELXL97.


Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: VM2202 ).


Acknowledgements

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.

References

Abid, O.-R., Qadeer, G., Rama, N. H. & Ruzicka, A. (2008). Acta Cryst. E64, o2223.  [CSD] [CrossRef] [IUCr Journals]
Bruker (2005). APEX2, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.
Garden, S. J., Pinto, A. C., Wardell, J. L., Low, J. N. & Glidewell, C. (2006). Acta Cryst. C62, o321-o323.  [CSD] [CrossRef] [IUCr Journals]
Ji, L., Fang, Q., Yuan, M. S., Liu, Z. Q., Shen, Y. X. & Chen, H. F. (2010). Org. Lett. 12, 5192-5195.  [Web of Science] [CSD] [CrossRef] [ChemPort] [PubMed]
Kurkin, A. V., Bernovskaya, A. A., Yurovskaya, M. A. & Rybakov, V. B. (2008). Acta Cryst. E64, o1448.  [CSD] [CrossRef] [IUCr Journals]
Macrae, C. F., Edgington, P. R., McCabe, P., Pidcock, E., Shields, G. P., Taylor, R., Towler, M. & van de Streek, J. (2006). J. Appl. Cryst. 39, 453-457.  [Web of Science] [CrossRef] [ChemPort] [IUCr Journals]
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.  [CrossRef] [ChemPort] [IUCr Journals]
Silva, J. F., Garden, S. J. & Pinto, A. C. (2001). J. Braz. Chem. Soc. 12, 273-324.  [CrossRef]


Acta Cryst (2014). E70, o67  [ doi:10.1107/S1600536813033539 ]

This is an open-access article distributed under the terms of the Creative Commons Attribution Licence, which permits unrestricted use, distribution, and reproduction in any medium, provided the original authors and source are cited.