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Volume 65 
Part 3 
Page o583  
March 2009  

Received 15 February 2009
Accepted 18 February 2009
Online 25 February 2009

Key indicators
Single-crystal X-ray study
T = 173 K
Mean [sigma](C-C) = 0.002 Å
R = 0.021
wR = 0.060
Data-to-parameter ratio = 14.3
Details
Open access

1-(2,6-Dichlorophenyl)indolin-2-one

aDepartment of Chemistry, Quaid-i-Azam Univeristy, Islamabad 45320, Pakistan,bDepartment of Chemistry, University of Sargodah, Sargodah, Pakistan, and cDepartment of Chemistry, Hong Kong Baptist University, Waterloo Road, Kowloon Tong, Hong Kong, People's Republic of China
Correspondence e-mail: qadeerqau@yahoo.com

In the molecule of the title compound, C14H9Cl2NO, the planar indole ring system [with a maximum deviation of 0.020 (2) Å for the N atom] is oriented at a dihedral angle of 72.17 (3)° with respect to the phenyl ring. In the crystal structure, weak intermolecular C-H...O hydrogen bonds link the molecules. A weak C-H...[pi] interaction may further stabilize the structure.

Related literature

For general background, see: Hibino & Choshi (2002[Hibino, S. & Choshi, T. (2002). Nat. Prod. Rep. 19, 148-180.]); Somei & Yamada (2003[Somei, M. & Yamada, F. (2003). Nat. Prod. Rep. 20, 216-242.]); Popp (1977[Popp, F. D. (1977). In Anticonvulsants, edited by J. A. Vida. New York: Academic Press.], 1984[Popp, F. D. (1984). J. Heterocycl. Chem. 21, 1641-1643.]). For related structures, see: Chakraborty & Talapatra (1985[Chakraborty, D. K. & Talapatra, S. K. (1985). Acta Cryst. C41, 1365-1366.]); Chakraborty et al. (1985[Chakraborty, D. K., Talapatra, S. K. & Chatterjee, A. (1985). Acta Cryst. C41, 1363-1364.]); De (1992[De, A. (1992). Acta Cryst. C48, 660-662.]); De & Kitagawa (1991a[De, A. & Kitagawa, Y. (1991a). Acta Cryst. C47, 2179-2181.],b[De, A. & Kitagawa, Y. (1991b). Acta Cryst. C47, 2384-2386.]); Itai et al. (1978[Itai, A., Iitaka, Y. & Kubo, A. (1978). Acta Cryst. B34, 3775-3777.]). For bond-length data, see: Allen et al. (1987[Allen, F. H., Kennard, O., Watson, D. G., Brammer, L., Orpen, A. G. & Taylor, R. (1987). J. Chem. Soc. Perkin Trans. 2, pp. S1-19.]).

[Scheme 1]

Experimental

Crystal data
  • C14H9Cl2NO

  • Mr = 278.12

  • Monoclinic, P 21

  • a = 7.1412 (8) Å

  • b = 8.0241 (9) Å

  • c = 11.0510 (13) Å

  • [beta] = 105.789 (2)°

  • V = 609.35 (12) Å3

  • Z = 2

  • Mo K[alpha] radiation

  • [mu] = 0.52 mm-1

  • T = 173 K

  • 0.30 × 0.24 × 0.20 mm

Data collection
  • Bruker SMART CCD area-detector diffractometer

  • Absorption correction: multi-scan (SADABS; Bruker, 2001[Bruker (2001). SMART and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.]) Tmin = 0.755, Tmax = 0.902

  • 3710 measured reflections

  • 2328 independent reflections

  • 2295 reflections with I > 2[sigma](I)

  • Rint = 0.014

Refinement
  • R[F2 > 2[sigma](F2)] = 0.021

  • wR(F2) = 0.060

  • S = 1.06

  • 2328 reflections

  • 163 parameters

  • 1 restraint

  • H-atom parameters constrained

  • [Delta][rho]max = 0.19 e Å-3

  • [Delta][rho]min = -0.16 e Å-3

  • Absolute structure: Flack (1983[Flack, H. D. (1983). Acta Cryst. A39, 876-881.]), 705 Friedel pairs

  • Flack parameter: -0.02 (4)

Table 1
Hydrogen-bond geometry (Å, °)

D-H...A D-H H...A D...A D-H...A
C4-H4A...O1i 0.95 2.55 3.2267 (19) 128
C8-H8A...Cg1ii 0.99 2.74 3.6125 (23) 147
Symmetry codes: (i) [-x, y+{\script{1\over 2}}, -z]; (ii) [-x+1, y-{\script{1\over 2}}, -z+1]. Cg1 is the centroid of the C9-C14 ring.

Data collection: SMART (Bruker, 2001[Bruker (2001). SMART and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.]); cell refinement: SAINT (Bruker, 2002[Bruker (2002). 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: ORTEP-3 for Windows (Farrugia, 1997[Farrugia, L. J. (1997). J. Appl. Cryst. 30, 565.]) and PLATON (Spek, 2009[Spek, A. L. (2009). Acta Cryst. D65, 148-155.]); software used to prepare material for publication: SHELXTL (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]) and PLATON.


Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: HK2625 ).


Acknowledgements

The authors gratefully acknowledge the financial support of the Higher Education Commission, Islamabad, Pakistan.

References

Allen, F. H., Kennard, O., Watson, D. G., Brammer, L., Orpen, A. G. & Taylor, R. (1987). J. Chem. Soc. Perkin Trans. 2, pp. S1-19.
Bruker (2001). SMART and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.
Bruker (2002). SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.
Chakraborty, D. K. & Talapatra, S. K. (1985). Acta Cryst. C41, 1365-1366.  [CrossRef] [details]
Chakraborty, D. K., Talapatra, S. K. & Chatterjee, A. (1985). Acta Cryst. C41, 1363-1364.  [CrossRef] [details]
De, A. (1992). Acta Cryst. C48, 660-662.  [CrossRef] [details]
De, A. & Kitagawa, Y. (1991a). Acta Cryst. C47, 2179-2181.  [CrossRef] [details]
De, A. & Kitagawa, Y. (1991b). Acta Cryst. C47, 2384-2386.  [CrossRef] [details]
Farrugia, L. J. (1997). J. Appl. Cryst. 30, 565.  [CrossRef] [details]
Flack, H. D. (1983). Acta Cryst. A39, 876-881.  [CrossRef] [details]
Hibino, S. & Choshi, T. (2002). Nat. Prod. Rep. 19, 148-180.  [CrossRef] [PubMed] [ChemPort]
Itai, A., Iitaka, Y. & Kubo, A. (1978). Acta Cryst. B34, 3775-3777.  [CrossRef] [details] [ISI]
Popp, F. D. (1977). In Anticonvulsants, edited by J. A. Vida. New York: Academic Press.
Popp, F. D. (1984). J. Heterocycl. Chem. 21, 1641-1643.  [ChemPort]
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.  [CrossRef] [details]
Somei, M. & Yamada, F. (2003). Nat. Prod. Rep. 20, 216-242.  [CrossRef] [PubMed] [ChemPort]
Spek, A. L. (2009). Acta Cryst. D65, 148-155.  [ISI] [CrossRef] [details]


Acta Cryst (2009). E65, o583  [ doi:10.1107/S1600536809005807 ]

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