4-Chloro-1-methyl­indoline-2,3-dione

Yu, J.G.; Tang, W.; Wang, D.C.; Xu, H.

doi:10.1107/S1600536811054171

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 (C-C) = 0.005 Å
R = 0.060
wR = 0.155
Data-to-parameter ratio = 12.5
Details

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

Jian Guang Yu,^a Wei Tang,^a De Cai Wang ^a ^* and Hong Xu ^b

^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-HO hydrogen bonds consolidate the crystal structure.

Related literature

For the preparation of the title compound, see: Bouhfid et al. (2005). For a related crystal structure and background to isatin derivatives, see: Liu et al. (2011).

Experimental

Crystal data

C₉H₆ClNO₂
M_r = 195.60
Monoclinic, P 2₁ /c
a = 7.4890 (15) Å
b = 14.825 (3) Å
c = 7.3140 (15) Å
= 90.27 (3)°
V = 812.0 (3) Å³
Z = 4
Mo K radiation
= 0.43 mm^-1
T = 293 K
0.20 × 0.10 × 0.10 mm

Data collection

Enraf-Nonius CAD-4 diffractometer
Absorption correction: scan (North et al., 1968) T_min = 0.919, T_max = 0.958
1607 measured reflections
1485 independent reflections
965 reflections with I > 2(I)
R_int = 0.042
3 standard reflections every 200 reflections intensity decay: 1%

Refinement

R[F² > 2(F²)] = 0.060
wR(F²) = 0.155
S = 1.00
1485 reflections
119 parameters
H-atom parameters constrained
_max = 0.28 e Å^-3
_min = -0.28 e Å^-3

Table 1
Hydrogen-bond geometry (Å, °)

D-HA	D-H	HA	DA	D-HA
C2-H2AO1ⁱ	0.93	2.58	3.323 (5)	137
C3-H3AO2ⁱ	0.93	2.50	3.424 (5)	170
C9-H9AO2ⁱⁱ	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); 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: 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.
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.
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.

organic compounds