5-Chloro-1-(4-meth­oxy­benz­yl)indoline-2,3-dione

Wu, W.; Zheng, T.; Cao, S.; Xiao, Z.

doi:10.1107/S1600536810052876

Volume 67
Part 2
Page o246
February 2011

Received 29 November 2010
Accepted 16 December 2010
Online 8 January 2011

Key indicators
Single-crystal X-ray study
T = 296 K
Mean (C-C) = 0.003 Å
R = 0.040
wR = 0.091
Data-to-parameter ratio = 17.2
Details

5-Chloro-1-(4-methoxybenzyl)indoline-2,3-dione

Weiyao Wu,^a Tingting Zheng,^a Shengli Cao ^a ^* and Zhichang Xiao ^a

^aDepartment of Chemistry, Capital Normal University, Beijing 100048, People's Republic of China
Correspondence e-mail: sl_cao@sohu.com

In the title compound, C₁₆H₁₂ClNO₃, an arm-like 4-methoxybenzene links to 5-chloroindoline-2,3-dione through a methylene group, with a dihedral angle between the mean planes of the benzene ring and the indole moiety of 88.44 (8)°. In the crystal, weak intermolecular C-HO and [pi] - [pi] stacking interactions [centroid-centroid distance = 3.383 (3) Å] link the molecules together to form a three-dimensional framework.

Related literature

For the antitumor activity of N-benzyl isatin analogs, see: Vine et al. (2007); Matesic et al. (2008); Penthala et al. (2010). For the preparation of the title compound, see: Itoh et al. (2009).

Experimental

Crystal data

C₁₆H₁₂ClNO₃
M_r = 301.72
Orthorhombic, P n a 2₁
a = 7.5318 (17) Å
b = 16.587 (4) Å
c = 11.220 (3) Å
V = 1401.7 (6) Å³
Z = 4
Mo K radiation
= 0.28 mm^-1
T = 296 K
0.30 × 0.22 × 0.10 mm

Data collection

Bruker APEXII CCD area-detector diffractometer
7665 measured reflections
3259 independent reflections
2113 reflections with I > 2(I)
R_int = 0.029

Refinement

R[F² > 2(F²)] = 0.040
wR(F²) = 0.091
S = 1.01
3259 reflections
190 parameters
1 restraint
H-atom parameters constrained
_max = 0.11 e Å^-3
_min = -0.14 e Å^-3
Absolute structure: Flack (1983), 1514 Friedel pairs
Flack parameter: -0.01 (7)

Table 1
Hydrogen-bond geometry (Å, °)

D-HA	D-H	HA	DA	D-HA
C16-H16CO1ⁱ	0.96	2.63	3.537 (4)	159
C1-H1AO2ⁱⁱ	0.93	2.58	3.391 (3)	146
Symmetry codes: (i) $[-x+1, -y+1, z+{\script{1\over 2}}]$ ; (ii) $[-x+{\script{3\over 2}}, y+{\script{1\over 2}}, z+{\script{1\over 2}}]$ .

Data collection: APEX2 (Bruker, 2007); cell refinement: APEX2 and SAINT (Bruker, 2007); data reduction: SAINT; 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: SHELXTL and PLATON (Spek, 2009).

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: ZQ2080 ).

Acknowledgements

This work was supported by the National Natural Science Foundation of China (project No. 20972099).

References

Bruker (2007). APEX2, SADABS and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.
Flack, H. D. (1983). Acta Cryst. A39, 876-881.
Itoh, T., Ishikawa, H. & Hayashi, Y. (2009). Org. Lett. 17, 3854-3857.
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.
Penthala, N. R., Yerramreddy, T. R., Madadi, N. R. & Crooks, P. A. (2010). Bioorg. Med. Chem. Lett. 20, 4468-4471.
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). J. Med. Chem. 50, 5109-5117.

organic compounds