(E)-5-Bromo-3-(2,6-dichloro­benzyl­idene)indolin-2-one

Zhang, H.; Ankati, H.; Akubathini, S.K.; Biehl, E.

doi:10.1107/S160053680903270X

Volume 65
Part 9
Page o2217
September 2009

Received 13 August 2009
Accepted 17 August 2009
Online 22 August 2009

Key indicators
Single-crystal X-ray study
T = 296 K
Mean (C-C) = 0.004 Å
R = 0.038
wR = 0.100
Data-to-parameter ratio = 18.9
Details

(E)-5-Bromo-3-(2,6-dichlorobenzylidene)indolin-2-one

Hongming Zhang,^a ^* Haribabu Ankati,^a Shashidhar Kumar Akubathini ^a and Ed Biehl ^a

^aDepartment of Chemistry, Southern Methodist University, Dallas, TX 75275, USA
Correspondence e-mail: hzhang@smu.edu

The title compound, C₁₅H₈BrCl₂NO, crystallizes with two independent molecules in the asymmetric unit. The dihedral angles between the two aromatic rings are 62.74 (9) and 63.50 (6)° in the two independent molecules. In the crystal, the molecules are connected by N-HO hydrogen bonds, forming two centrosymmetric dimers.

Related literature

For the pharmacological properties of 3-substituted indoline-2-ones, see: Andreani et al. (2006); Johnson et al. (2005); Sun et al. (2003). a series of 3-substituted indoline-2-one derivatives have been synthesized in our laboratory and their neuroprotective activities have been tested, see: Ankati et al., (2009); Balderamos et al. (2008). For the structures of some of the derivatives, see: Zhang et al. (2008, 2009a,b).

Experimental

Crystal data

C₁₅H₈BrCl₂NO
M_r = 369.03
Triclinic, $[P \overline 1]$
a = 8.1018 (4) Å
b = 13.5726 (7) Å
c = 14.4904 (7) Å
= 63.575 (1)°
= 82.956 (1)°
= 80.139 (1)°
V = 1403.89 (12) Å³
Z = 4
Mo K radiation
= 3.30 mm^-1
T = 296 K
0.32 × 0.21 × 0.15 mm

Data collection

Bruker SMART APEX diffractometer
Absorption correction: multi-scan (SADABS; Sheldrick, 1996) T_min = 0.416, T_max = 0.636
17925 measured reflections
6832 independent reflections
5263 reflections with I > 2(I)
R_int = 0.017

Refinement

R[F² > 2(F²)] = 0.038
wR(F²) = 0.100
S = 1.05
6832 reflections
361 parameters
H-atom parameters constrained
_max = 0.71 e Å^-3
_min = -0.76 e Å^-3

Table 1
Hydrogen-bond geometry (Å, °)

D-HA	D-H	HA	DA	D-HA
N21-H21O22ⁱ	0.86	2.03	2.848 (3)	160
N1-H1O2ⁱⁱ	0.86	2.09	2.924 (3)	163
Symmetry codes: (i) -x+2, -y+1, -z+1; (ii) -x+1, -y+1, -z+1.

Data collection: SMART (Bruker, 1997); cell refinement: SAINT (Bruker, 1997); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXTL and publCIF (Westrip, 2009).

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: BT5036 ).

Acknowledgements

The authors are grateful for grants from the Welch Foundation (N-118) and the DARPA (HR0011-06-1-0032).

References

Andreani, A., Burnelli, S., Granaiola, M., Leoni, A., Locatelli, A., Morigi, R., Rambaldi, M., Varoli, L. & Kunkel, M. W. (2006). J. Med. Chem. 49, 6922-6924.
Ankati, H., Akubathini, S. K., Kamila, S., Mukherjee, C., D'Mello, S. R. & Biehl, E. R. (2009). Open Org. Chem. J. 3, 1-10.
Balderamos, M., Ankati, H., Akubathini, S. K., Patel, A. V., Kamila, S., Mukherjee, C., Wang, L., Biehl, E. & D'Mello, S. (2008). Exp. Biol. Med. 233, 1395-1402.
Bruker (1997). SMART and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.
Johnson, K., Liu, L., Majdzadeh, N., Chavez, C., Chin, P. C., Morrison, B., Wang, L., Park, J., Chugh, P., Chen, H. & D'Mello, S. R. (2005). J. Neurochem. 93, 538-548.
Sheldrick, G. M. (1996). SADABS. University of Göttingen, Germany.
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.
Sun, L., Liang, C., Shirazian, S., Zhou, Y., Miller, T., Cui, J., Fukuda, J. Y., Chu, J. Y., Nematalla, A., Wang, X., Chen, H., Sistla, A., Luu, T. C., Tang, F., Wei, J. & Tang, C. (2003). J. Med. Chem. 46, 1116-1119.
Westrip, S. P. (2009). publCIF. In preparation.
Zhang, H., Akubathini, S. K., Ankati, H. & Biehl, E. (2009b). Acta Cryst. E65, o363.
Zhang, H., Ankati, H., Akubathini, S. K. & Biehl, E. (2008). Acta Cryst. E64, o2103.
Zhang, H., Ankati, H., Akubathini, S. K. & Biehl, E. (2009a). Acta Cryst. E65, o8.

organic compounds