[Journal logo]

Volume 69 
Part 6 
Page o856  
June 2013  

Received 10 April 2013
Accepted 30 April 2013
Online 11 May 2013

Key indicators
Single-crystal X-ray study
T = 293 K
Mean [sigma](C-C) = 0.002 Å
R = 0.038
wR = 0.138
Data-to-parameter ratio = 17.9
Details
Open access

Methyl 2-(5-chloro-1-methyl-2-oxo-2,3-dihydro-1H-indol-3-ylidene)acetate

aDepartment of Physics, S.M.K. Fomra Institute of Technology, Thaiyur, Chennai 603 103, India,bIndustrial Chemistry Laboratory, Central Leather Research Institute, Adyar, Chennai 600 020, India, and cDepartment of Physics, Presidency College (Autonomous), Chennai 600 005, India
Correspondence e-mail: a_sp59@yahoo.in

The title compound, C12H10ClNO3, the indoline ring system is essentially planar, with a maximum deviation of 0.009 Å for the N atom. The indoline ring and acetate group are essentially coplanar, with a maximum deviation of 0.086 Å for the O atom. The mean plane through the methoxycarbonylmethyl group forms a dihedral angle of 3.68 (5)° with the plane of the indoline ring system. The molecular structure is stabilized by an intramolecular C-H...O hydrogen-bond interaction. In the crystal, [pi]-[pi] stacking interactions [centroid-centroid distance = 3.7677 (8) Å] occur between benzene rings, forming a chain running along the c-axis direction.

Related literature

For the biological activity of indole derivatives, see: Chai et al. (2006[Chai, H., Zhao, C. & Gong, P. (2006). Bioorg. Med. Chem. 14, 911-917.]); Nieto et al. (2005[Nieto, M. J., Alovero, F. L., Manzo, R. H. & Mazzieri, M. R. (2005). Eur. J. Med. Chem. 40, 361-369.]); Singh et al. (2000[Singh, U. P., Sarma, B. K., Mishra, P. K. & Ray, A. B. (2000). Folia Microbiol. (Praha), 45, 173-176.]); Andreani et al. (2001[Andreani, A., Granaiola, M., Leoni, A., Locatelli, A., Morigi, R., Rambaldi, M., Giorgi, G., Salvini, L. & Garaliene, V. (2001). Anticancer Drug Des. 16, 167-174.]); Quetin-Leclercq (1994[Quetin-Leclercq, J. (1994). J. Pharm. Belg. 49, 181-192.]); Mukhopadhyay et al. (1981[Mukhopadhyay, S., Handy, G. A., Funayama, S. & Cordell, G. A. (1981). J. Nat. Prod. 44, 696-700.]); Taylor et al. (1999[Taylor, D. L., Ahmed, P. S., Chambers, P., Tyms, A. S., Bedard, J., Duchaine, J., Falardeau, G., Lavallee, J. F., Brown, W., Rando, R. F. & Bowlin, T. (1999). Antivir. Chem. Chemother. 10, 79-86.]). For closely related structures, see: Hu et al. (2011[Hu, F., Zheng, L., Zeng, X. C. & Li, K. P. (2011). Acta Cryst. E67, o742.]); Han & Luo (2012[Han, X.-L. & Luo, Y.-H. (2012). Acta Cryst. E68, o145.]); Deng (2011[Deng, Q. (2011). Acta Cryst. E67, o897.]). For puckering parameters, see: Cremer & Pople (1975[Cremer, D. & Pople, J. A. (1975). J. Am. Chem. Soc. 97, 1354-1358.]).

[Scheme 1]

Experimental

Crystal data
  • C12H10ClNO3

  • Mr = 251.66

  • Monoclinic, P 21 /c

  • a = 8.4709 (7) Å

  • b = 17.1658 (13) Å

  • c = 7.9481 (6) Å

  • [beta] = 107.228 (4)°

  • V = 1103.88 (15) Å3

  • Z = 4

  • Mo K[alpha] radiation

  • [mu] = 0.34 mm-1

  • T = 293 K

  • 0.30 × 0.25 × 0.20 mm

Data collection
  • Bruker SMART APEXII area-detector diffractometer

  • Absorption correction: multi-scan (SADABS; Bruker, 2008[Bruker (2008). APEX2, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.]) Tmin = 0.903, Tmax = 0.934

  • 10447 measured reflections

  • 2815 independent reflections

  • 2410 reflections with I > 2[sigma](I)

  • Rint = 0.031

Refinement
  • R[F2 > 2[sigma](F2)] = 0.038

  • wR(F2) = 0.138

  • S = 1.13

  • 2815 reflections

  • 157 parameters

  • H-atom parameters constrained

  • [Delta][rho]max = 0.34 e Å-3

  • [Delta][rho]min = -0.21 e Å-3

Table 1
Hydrogen-bond geometry (Å, °)

D-H...A D-H H...A D...A D-H...A
C6-H6...O2 0.93 2.30 3.0181 (17) 134

Data collection: APEX2 (Bruker, 2008[Bruker (2008). APEX2, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.]); cell refinement: SAINT (Bruker, 2008[Bruker (2008). APEX2, SAINT and SADABS. 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: ORTEP-3 for Windows (Farrugia, 2012[Farrugia, L. J. (2012). J. Appl. Cryst. 45, 849-854.]); software used to prepare material for publication: SHELXL97 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: BX2438 ).


Acknowledgements

The authors thank the TBI X-ray facility, CAS in Crystallography and BioPhysics, University of Madras, Chennai, India, for the data collection.

References

Andreani, A., Granaiola, M., Leoni, A., Locatelli, A., Morigi, R., Rambaldi, M., Giorgi, G., Salvini, L. & Garaliene, V. (2001). Anticancer Drug Des. 16, 167-174.  [PubMed] [ChemPort]
Bruker (2008). APEX2, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.
Chai, H., Zhao, C. & Gong, P. (2006). Bioorg. Med. Chem. 14, 911-917.  [CrossRef] [PubMed] [ChemPort]
Cremer, D. & Pople, J. A. (1975). J. Am. Chem. Soc. 97, 1354-1358.  [CrossRef] [ChemPort] [ISI]
Deng, Q. (2011). Acta Cryst. E67, o897.  [CSD] [CrossRef] [details]
Farrugia, L. J. (2012). J. Appl. Cryst. 45, 849-854.  [ISI] [CrossRef] [ChemPort] [details]
Han, X.-L. & Luo, Y.-H. (2012). Acta Cryst. E68, o145.  [CSD] [CrossRef] [details]
Hu, F., Zheng, L., Zeng, X. C. & Li, K. P. (2011). Acta Cryst. E67, o742.  [CSD] [CrossRef] [details]
Mukhopadhyay, S., Handy, G. A., Funayama, S. & Cordell, G. A. (1981). J. Nat. Prod. 44, 696-700.  [CrossRef] [ChemPort] [PubMed] [ISI]
Nieto, M. J., Alovero, F. L., Manzo, R. H. & Mazzieri, M. R. (2005). Eur. J. Med. Chem. 40, 361-369.  [ISI] [CrossRef] [PubMed] [ChemPort]
Quetin-Leclercq, J. (1994). J. Pharm. Belg. 49, 181-192.  [ChemPort] [PubMed]
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.  [CrossRef] [ChemPort] [details]
Singh, U. P., Sarma, B. K., Mishra, P. K. & Ray, A. B. (2000). Folia Microbiol. (Praha), 45, 173-176.  [CrossRef] [PubMed] [ChemPort]
Spek, A. L. (2009). Acta Cryst. D65, 148-155.  [ISI] [CrossRef] [ChemPort] [details]
Taylor, D. L., Ahmed, P. S., Chambers, P., Tyms, A. S., Bedard, J., Duchaine, J., Falardeau, G., Lavallee, J. F., Brown, W., Rando, R. F. & Bowlin, T. (1999). Antivir. Chem. Chemother. 10, 79-86.  [PubMed] [ChemPort]


Acta Cryst (2013). E69, o856  [ doi:10.1107/S1600536813011768 ]

This is an open-access article distributed under the terms of the Creative Commons Attribution Licence, which permits unrestricted use, distribution, and reproduction in any medium, provided the original authors and source are cited.