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Volume 68 
Part 1 
Page o14  
January 2012  

Received 15 November 2011
Accepted 29 November 2011
Online 3 December 2011

Key indicators
Single-crystal X-ray study
T = 293 K
Mean [sigma](C-C) = 0.003 Å
R = 0.040
wR = 0.118
Data-to-parameter ratio = 13.1
Details
Open access

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

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

The title molecule, C9H6ClNO2, is essentially planar: the maximum deviation from the mean plane of the indoline ring is 0.020 (2) Å and the substituents do not deviate by more than 0.053 (2) Å from this plane. C-H...O hydrogen bonds help to consolidate the crystal structure.

Related literature

The title compound is a halogenated derivative of isatin. For the cytotoxic and antineoplastic activity of halogenated isatin derivatives, see: Vine et al. (2007[Vine, K. L., Locke, J. M., Ranson, M., Pyne, S. G. & Bremner, J. B. (2007). Bioorg. Med. Chem. 15, 931-938.]); Matesic et al. (2008[Matesic, L., Locke, J. M., Bremner, J. B., Pyne, S. G., Skropeta, D., Ranson, M. & Vine, K. L. (2008). Bioorg. Med. Chem. 16, 3118-3124.]). 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 structure, see: Wu et al. (2011[Wu, W., Zheng, T., Cao, S. & Xiao, Z. (2011). Acta Cryst. E67, o246.]).

[Scheme 1]

Experimental

Crystal data
  • C9H6ClNO2

  • Mr = 195.60

  • Monoclinic, C 2/c

  • a = 13.077 (3) Å

  • b = 7.9390 (16) Å

  • c = 16.673 (3) Å

  • [beta] = 101.95 (3)°

  • V = 1693.5 (6) Å3

  • Z = 8

  • Mo K[alpha] radiation

  • [mu] = 0.41 mm-1

  • T = 293 K

  • 0.30 × 0.20 × 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 = 0.887, Tmax = 0.960

  • 3124 measured reflections

  • 1557 independent reflections

  • 1250 reflections with I > 2[sigma](I)

  • Rint = 0.031

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

Refinement
  • R[F2 > 2[sigma](F2)] = 0.040

  • wR(F2) = 0.118

  • S = 1.00

  • 1557 reflections

  • 119 parameters

  • 1 restraint

  • H-atom parameters constrained

  • [Delta][rho]max = 0.17 e Å-3

  • [Delta][rho]min = -0.27 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 2.50 3.419 (2) 168
Symmetry code: (i) [x-{\script{1\over 2}}, y-{\script{1\over 2}}, z].

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: PV2487 ).


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.
Matesic, L., Locke, J. M., Bremner, J. B., Pyne, S. G., Skropeta, D., Ranson, M. & Vine, K. L. (2008). Bioorg. Med. Chem. 16, 3118-3124.  [CrossRef] [PubMed] [ChemPort]
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]
Vine, K. L., Locke, J. M., Ranson, M., Pyne, S. G. & Bremner, J. B. (2007). Bioorg. Med. Chem. 15, 931-938.  [CrossRef] [PubMed] [ChemPort]
Wu, W., Zheng, T., Cao, S. & Xiao, Z. (2011). Acta Cryst. E67, o246.  [CSD] [CrossRef] [details]


Acta Cryst (2012). E68, o14  [ doi:10.1107/S1600536811051294 ]

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