6-Chloro-1-methyl­indoline-2,3-dione

Liu, H.Q.; Tang, W.; Wang, D.C.; Ou-yang, P.K.

doi:10.1107/S1600536811051294

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 (C-C) = 0.003 Å
R = 0.040
wR = 0.118
Data-to-parameter ratio = 13.1
Details

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

Hua Quan Liu,^a Wei Tang,^a De Cai Wang ^a ^* and Ping Kai Ou-yang ^a

^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-HO 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); Matesic et al. (2008). For the preparation of the title compound, see: Bouhfid et al. (2005). For a related structure, see: Wu et al. (2011).

Experimental

Crystal data

C₉H₆ClNO₂
M_r = 195.60
Monoclinic, C 2/c
a = 13.077 (3) Å
b = 7.9390 (16) Å
c = 16.673 (3) Å
= 101.95 (3)°
V = 1693.5 (6) Å³
Z = 8
Mo K radiation
= 0.41 mm^-1
T = 293 K
0.30 × 0.20 × 0.10 mm

Data collection

Enraf-Nonius CAD-4 diffractometer
Absorption correction: scan (North et al., 1968) T_min = 0.887, T_max = 0.960
3124 measured reflections
1557 independent reflections
1250 reflections with I > 2(I)
R_int = 0.031
3 standard reflections every 200 reflections intensity decay: 1%

Refinement

R[F² > 2(F²)] = 0.040
wR(F²) = 0.118
S = 1.00
1557 reflections
119 parameters
1 restraint
H-atom parameters constrained
_max = 0.17 e Å^-3
_min = -0.27 e Å^-3

Table 1
Hydrogen-bond geometry (Å, °)

D-HA	D-H	HA	DA	D-HA
C2-H2AO1ⁱ	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); cell refinement: CAD-4 EXPRESS; data reduction: XCAD4 (Harms & Wocadlo, 1995); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: PLATON (Spek, 2009).

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.
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.
North, A. C. T., Phillips, D. C. & Mathews, F. S. (1968). Acta Cryst. A24, 351-359.
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.
Spek, A. L. (2009). Acta Cryst. D65, 148-155.
Vine, K. L., Locke, J. M., Ranson, M., Pyne, S. G. & Bremner, J. B. (2007). Bioorg. Med. Chem. 15, 931-938.
Wu, W., Zheng, T., Cao, S. & Xiao, Z. (2011). Acta Cryst. E67, o246.

organic compounds