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Volume 68 
Part 1 
Page o219  
January 2012  

Received 5 December 2011
Accepted 16 December 2011
Online 23 December 2011

Key indicators
Single-crystal X-ray study
T = 293 K
Mean [sigma](C-C) = 0.005 Å
R = 0.060
wR = 0.155
Data-to-parameter ratio = 12.5
Details
Open access

4-Chloro-1-methylindoline-2,3-dione

aState Key Laboratory of Materials-Oriented Chemical Engineering, College of Life Science and Pharmaceutical Engineering, Nanjing University of Technology, No. 5 Xinmofan Road, Nanjing 210009, People's Republic of China, and bState Key Laboratory of Materials-Oriented Chemical Engineering, College of Food Science and Light Industry, Nanjing University of Technology, No. 5 Xinmofan Road, Nanjing 210009, People's Republic of China
Correspondence e-mail: dc_wang@hotmail.com

The title molecule, C9H6ClNO2, is essentially planar; the maximum deviation of the indoline ring system is 0.027 (3) Å and the substituents do not deviate by more than 0.075 (2) Å from this plane. Intermolecular C-H...O hydrogen bonds consolidate the crystal structure.

Related literature

For the preparation of the title compound, see: Bouhfid et al. (2005[Bouhfid, R., Joly, N., Massoui, M., Cecchelli, R., Lequart, V., Martin, P. & Essassi, E. M. (2005). Heterocycles, 65, 2949-2955.]). For a related crystal structure and background to isatin derivatives, see: Liu et al. (2011[Liu, H., Fan, D., Wang, D. & Ou-yang, P.-K. (2011). Acta Cryst. E67, o3427.]).

[Scheme 1]

Experimental

Crystal data
  • C9H6ClNO2

  • Mr = 195.60

  • Monoclinic, P 21 /c

  • a = 7.4890 (15) Å

  • b = 14.825 (3) Å

  • c = 7.3140 (15) Å

  • [beta] = 90.27 (3)°

  • V = 812.0 (3) Å3

  • Z = 4

  • Mo K[alpha] radiation

  • [mu] = 0.43 mm-1

  • T = 293 K

  • 0.20 × 0.10 × 0.10 mm

Data collection
  • Enraf-Nonius CAD-4 diffractometer

  • Absorption correction: [psi] scan (North et al., 1968[North, A. C. T., Phillips, D. C. & Mathews, F. S. (1968). Acta Cryst. A24, 351-359.]) Tmin = 0.919, Tmax = 0.958

  • 1607 measured reflections

  • 1485 independent reflections

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

  • Rint = 0.042

  • 3 standard reflections every 200 reflections intensity decay: 1%

Refinement
  • R[F2 > 2[sigma](F2)] = 0.060

  • wR(F2) = 0.155

  • S = 1.00

  • 1485 reflections

  • 119 parameters

  • H-atom parameters constrained

  • [Delta][rho]max = 0.28 e Å-3

  • [Delta][rho]min = -0.28 e Å-3

Table 1
Hydrogen-bond geometry (Å, °)

D-H...A D-H H...A D...A D-H...A
C2-H2A...O1i 0.93 2.58 3.323 (5) 137
C3-H3A...O2i 0.93 2.50 3.424 (5) 170
C9-H9A...O2ii 0.96 2.60 3.198 (5) 121
Symmetry codes: (i) [x-1, -y+{\script{3\over 2}}, z-{\script{1\over 2}}]; (ii) [-x+1, y+{\script{1\over 2}}, -z+{\script{1\over 2}}].

Data collection: CAD-4 EXPRESS (Enraf-Nonius, 1994[Enraf-Nonius (1994). CAD-4 EXPRESS. Enraf-Nonius, Delft, The Netherlands.]); cell refinement: CAD-4 EXPRESS; data reduction: XCAD4 (Harms & Wocadlo, 1995[Harms, K. & Wocadlo, S. (1995). XCAD4. University of Marburg, Germany.]); 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.]); software used to prepare material for publication: PLATON (Spek, 2009[Spek, A. L. (2009). Acta Cryst. D65, 148-155.]).


Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: PV2493 ).


Acknowledgements

The authors thank the Center of Testing and Analysis, Nanjing University, for support.

References

Bouhfid, R., Joly, N., Massoui, M., Cecchelli, R., Lequart, V., Martin, P. & Essassi, E. M. (2005). Heterocycles, 65, 2949-2955.  [ChemPort]
Enraf-Nonius (1994). CAD-4 EXPRESS. Enraf-Nonius, Delft, The Netherlands.
Harms, K. & Wocadlo, S. (1995). XCAD4. University of Marburg, Germany.
Liu, H., Fan, D., Wang, D. & Ou-yang, P.-K. (2011). Acta Cryst. E67, o3427.  [CrossRef] [details]
North, A. C. T., Phillips, D. C. & Mathews, F. S. (1968). Acta Cryst. A24, 351-359.  [CrossRef] [details]
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.  [CrossRef] [details]
Spek, A. L. (2009). Acta Cryst. D65, 148-155.  [ISI] [CrossRef] [details]


Acta Cryst (2012). E68, o219  [ doi:10.1107/S1600536811054171 ]

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