1-(2,6-Dichloro­phen­yl)indolin-2-one

Hanif, M.; Rafiq, M.; Saleem, M.; Qadeer, G.; Wong, W.-Y.

doi:10.1107/S1600536809005807

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 (C-C) = 0.002 Å
R = 0.021
wR = 0.060
Data-to-parameter ratio = 14.3
Details

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

Muhammad Hanif,^a Muhammad Rafiq,^a Muhammad Saleem,^b Ghulam Qadeer ^a ^* and Wai-Yeung Wong ^c ⁺

^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-HO 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); Somei & Yamada (2003); Popp (1977, 1984). For related structures, see: Chakraborty & Talapatra (1985); Chakraborty et al. (1985); De (1992); De & Kitagawa (1991a,b); Itai et al. (1978). For bond-length data, see: Allen et al. (1987).

Experimental

Crystal data

C₁₄H₉Cl₂NO
M_r = 278.12
Monoclinic, P 2₁
a = 7.1412 (8) Å
b = 8.0241 (9) Å
c = 11.0510 (13) Å
= 105.789 (2)°
V = 609.35 (12) Å³
Z = 2
Mo K radiation
= 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) T_min = 0.755, T_max = 0.902
3710 measured reflections
2328 independent reflections
2295 reflections with I > 2(I)
R_int = 0.014

Refinement

R[F² > 2(F²)] = 0.021
wR(F²) = 0.060
S = 1.06
2328 reflections
163 parameters
1 restraint
H-atom parameters constrained
_max = 0.19 e Å^-3
_min = -0.16 e Å^-3
Absolute structure: Flack (1983), 705 Friedel pairs
Flack parameter: -0.02 (4)

Table 1
Hydrogen-bond geometry (Å, °)

D-HA	D-H	HA	DA	D-HA
C4-H4AO1ⁱ	0.95	2.55	3.2267 (19)	128
C8-H8ACg1ⁱⁱ	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); cell refinement: SAINT (Bruker, 2002); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997) and PLATON (Spek, 2009); software used to prepare material for publication: SHELXTL (Sheldrick, 2008) 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.
Chakraborty, D. K., Talapatra, S. K. & Chatterjee, A. (1985). Acta Cryst. C41, 1363-1364.
De, A. (1992). Acta Cryst. C48, 660-662.
De, A. & Kitagawa, Y. (1991a). Acta Cryst. C47, 2179-2181.
De, A. & Kitagawa, Y. (1991b). Acta Cryst. C47, 2384-2386.
Farrugia, L. J. (1997). J. Appl. Cryst. 30, 565.
Flack, H. D. (1983). Acta Cryst. A39, 876-881.
Hibino, S. & Choshi, T. (2002). Nat. Prod. Rep. 19, 148-180.
Itai, A., Iitaka, Y. & Kubo, A. (1978). Acta Cryst. B34, 3775-3777.
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.
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.
Somei, M. & Yamada, F. (2003). Nat. Prod. Rep. 20, 216-242.
Spek, A. L. (2009). Acta Cryst. D65, 148-155.

organic compounds