5,6-Dichloro-2-(3-methoxy­phen­yl)isoindoline-1,3-dione

Büyükgüngör, O.; Odabaşoğlu, M.

doi:10.1107/S1600536808010659

Volume 64
Part 5
Page o881
May 2008

Received 4 April 2008
Accepted 17 April 2008
Online 23 April 2008

Key indicators
Single-crystal X-ray study
T = 296 K
Mean (C-C) = 0.006 Å
R = 0.071
wR = 0.170
Data-to-parameter ratio = 14.0
Details

5,6-Dichloro-2-(3-methoxyphenyl)isoindoline-1,3-dione

Orhan Büyükgüngör ^a ^* and Mustafa Odabasoglu ^b

^aDepartment of Physics, Faculty of Arts and Sciences, Ondokuz Mayis University, TR-55139 Kurupelit Samsun, Turkey, and ^bDepartment of Chemistry, Faculty of Arts and Sciences, Ondokuz Mayis University, TR-55139 Kurupelit Samsun, Turkey
Correspondence e-mail: orhanb@omu.edu.tr

The title compound, C₁₅H₉Cl₂NO₃, crystallizes as an inversion twin, the ratio of the twin components being 0.43 (13):0.57 (13). The isoindoline group is planar and inclined by 77.63 (3)° to the aromatic ring substituent. The crystal structure is stabilized by aromatic [pi] - [pi] stacking interactions involving the benzene rings of adjacent isoindoline groups, with a centroid-centroid distance of 3.664 (7) Å and an interplanar separation of 3.409 Å.

Related literature

For general background, see: Chapman et al. (1979); Hall et al., (1983; 1987); Srivastava et al. (2001); Abdel-Hafez (2004); Sena et al. (2007).

Experimental

Crystal data

C₁₅H₉Cl₂NO₃
M_r = 322.13
Orthorhombic, P 2₁ 2₁ 2₁
a = 6.8689 (5) Å
b = 9.7362 (10) Å
c = 20.4271 (14) Å
V = 1366.1 (2) Å³
Z = 4
Mo K radiation
= 0.48 mm^-1
T = 296 K
0.65 × 0.51 × 0.23 mm

Data collection

Stoe IPDSII diffractometer
Absorption correction: integration (X-RED32; Stoe & Cie, 2002) T_min = 0.685, T_max = 0.888
6123 measured reflections
2687 independent reflections
2076 reflections with I > 2(I)
R_int = 0.117

Refinement

R[F² > 2(F²)] = 0.071
wR(F²) = 0.169
S = 1.00
2687 reflections
192 parameters
H-atom parameters constrained
_max = 0.63 e Å^-3
_min = -0.57 e Å^-3
Absolute structure: Flack (1983), 1114 Friedel pairs
Flack parameter: 0.43 (13)

Data collection: X-AREA (Stoe & Cie, 2002); cell refinement: X-AREA; data reduction: X-RED32 (Stoe & Cie, 2002); 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); software used to prepare material for publication: WinGX (Farrugia, 1999).

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: RZ2205 ).

Acknowledgements

The authors acknowledge the Faculty of Arts and Sciences, Ondokuz Mayis University, Turkey, for the use of the Stoe IPDSII diffractometer (purchased under grant F.279 of the University Research Fund).

References

Abdel-Hafez, A. A. M. (2004). Arch. Pharm. Res. 27, 495-501.
Chapman, J. M., Cocolas, G. H. & Hall, I. H. (1979). J. Med. Chem. 22, 1399-1402.
Farrugia, L. J. (1997). J. Appl. Cryst. 30, 565.
Farrugia, L. J. (1999). J. Appl. Cryst. 32, 837-838.
Flack, H. D. (1983). Acta Cryst. A39, 876-881.
Hall, I. H., Reynolds, D. J., Wong, O. T., Oswald, C. B. & Murthy, A. R. K. (1987). Pharm. Res. 4, 472-479.
Hall, I. H., Voorstad, P. J., Chapman, J. M. & Cocolas, G. H. (1983). J. Pharm. Sci. 72, 845-851.
Sena, V. L. M., Srivastava, M. R., de Simone, C. A., da Cruz Gonçalves, S. M., Silva, R. O. & Pereira, M. A. (2007). J. Braz. Chem. Soc. 18, 1224-1234.
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.
Srivastava, R. M., Oliveira, F. J. S., da Silva, L. P., de Freitas Filho, J. R., Oliveira, S. P. & Lima, V. L. M. (2001). Carbohydr. Res. 332, 335-340.
Stoe & Cie (2002). X-AREA and X-RED32. Stoe & Cie, Darmstadt, Germany.

organic compounds