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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 [sigma](C-C) = 0.003 Å
R = 0.040
wR = 0.091
Data-to-parameter ratio = 17.2
Details
Open access

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

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-H...O 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[Vine, K. L., Locke, J. M., Ranson, M., Pyne, S. G. & Bremner, J. B. (2007). J. Med. Chem. 50, 5109-5117.]); 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.]); Penthala et al. (2010[Penthala, N. R., Yerramreddy, T. R., Madadi, N. R. & Crooks, P. A. (2010). Bioorg. Med. Chem. Lett. 20, 4468-4471.]). For the preparation of the title compound, see: Itoh et al. (2009[Itoh, T., Ishikawa, H. & Hayashi, Y. (2009). Org. Lett. 17, 3854-3857.]).

[Scheme 1]

Experimental

Crystal data
  • C16H12ClNO3

  • Mr = 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[alpha] radiation

  • [mu] = 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[sigma](I)

  • Rint = 0.029

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

  • wR(F2) = 0.091

  • S = 1.01

  • 3259 reflections

  • 190 parameters

  • 1 restraint

  • H-atom parameters constrained

  • [Delta][rho]max = 0.11 e Å-3

  • [Delta][rho]min = -0.14 e Å-3

  • Absolute structure: Flack (1983[Flack, H. D. (1983). Acta Cryst. A39, 876-881.]), 1514 Friedel pairs

  • Flack parameter: -0.01 (7)

Table 1
Hydrogen-bond geometry (Å, °)

D-H...A D-H H...A D...A D-H...A
C16-H16C...O1i 0.96 2.63 3.537 (4) 159
C1-H1A...O2ii 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[Bruker (2007). APEX2, SADABS and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.]); cell refinement: APEX2 and SAINT (Bruker, 2007[Bruker (2007). APEX2, SADABS and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.]); data reduction: SAINT; 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: SHELXTL and 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: 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.  [CrossRef] [details]
Itoh, T., Ishikawa, H. & Hayashi, Y. (2009). Org. Lett. 17, 3854-3857.  [CrossRef]
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]
Penthala, N. R., Yerramreddy, T. R., Madadi, N. R. & Crooks, P. A. (2010). Bioorg. Med. Chem. Lett. 20, 4468-4471.  [CrossRef] [ChemPort] [PubMed]
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). J. Med. Chem. 50, 5109-5117.  [ISI] [CrossRef] [PubMed] [ChemPort]


Acta Cryst (2011). E67, o246  [ doi:10.1107/S1600536810052876 ]

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