3,4-Bis(4-bromo­phen­yl)-N-phenyl­maleimide

Liu, Y.; Zheng, S.; Zhou, J.; Gao, D.; Du, Z.-T.

doi:10.1107/S1600536811014152

Volume 67
Part 5
Page o1198
May 2011

Received 2 April 2011
Accepted 15 April 2011
Online 22 April 2011

Key indicators
Single-crystal X-ray study
T = 296 K
Mean (C-C) = 0.011 Å
R = 0.050
wR = 0.133
Data-to-parameter ratio = 13.9
Details

3,4-Bis(4-bromophenyl)-N-phenylmaleimide

Yong Liu,^a Shuai Zheng,^b Jing Zhou,^b Dongmei Gao ^b and Zhen-Ting Du ^b ^*

^aMedical College, Northwest University for Nationalities, Lanzhou 730030, Gansu Province, People's Republic of China, and ^bCollege of Science, Northwest A&F University, Yangling 712100, Shannxi Province, People's Republic of China
Correspondence e-mail: duzt@nwsuaf.edu.cn

In the title molecule, C₂₂H₁₃Br₂NO₂, the three benzene rings are arranged in a propeller-like fashion around the central malemide ring, making dihedral angles of 48.2 (4), 30.2 (4) and 34.8 (4)° with the malemide ring. The C-C single-bond lengths connecting benzene groups and maleimide are significantly shorter [C-C = 1.468 (9) and 1.478 (9) Å] than a typical Csp³-Csp³ single bond, indicating partial conjugation between the benzene and the maleimide. A weak nonclassical C-HO hydrogen bond helps to stabilize the crystal structure.

Related literature

For general background to 3,4-diaryl-substituted maleimide derivatives, see: Fujii et al. (2001); Onimura et al. (2010); Shorunov et al. (2006).

Experimental

Crystal data

C₂₂H₁₃Br₂NO₂
M_r = 483.13
Monoclinic, P 2₁ /c
a = 10.844 (5) Å
b = 18.594 (9) Å
c = 9.602 (5) Å
= 102.760 (6)°
V = 1888.3 (16) Å³
Z = 4
Mo K radiation
= 4.31 mm^-1
T = 296 K
0.32 × 0.30 × 0.24 mm

Data collection

Bruker APEXII CCD diffractometer
Absorption correction: multi-scan (SADABS; Sheldrick, 1998) T_min = 0.339, T_max = 0.424
8594 measured reflections
3382 independent reflections
1427 reflections with I > 2(I)
R_int = 0.117

Refinement

R[F² > 2(F²)] = 0.050
wR(F²) = 0.133
S = 0.94
3382 reflections
244 parameters
H-atom parameters constrained
_max = 0.51 e Å^-3
_min = -0.71 e Å^-3

Table 1
Hydrogen-bond geometry (Å, °)

D-HA	D-H	HA	DA	D-HA
C21-H21O1ⁱ	0.93	2.41	3.267 (9)	153
Symmetry code: (i) $[-x+1, y-{\script{1\over 2}}, -z+{\script{1\over 2}}]$ .

Data collection: APEX2 (Bruker, 2005); cell refinement: SAINT (Bruker, 2001); 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.

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: RK2272 ).

Acknowledgements

Financial support from the Fundamental Research Funds for the Central Universities in NWSUAF (QN2009048) and the Excellent Young Funds 211020712 is greatly appreciated.

References

Bruker (2001). SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.
Bruker (2005). APEX2. Bruker AXS Inc., Madison, Wisconsin, USA.
Fujii, I., Ohtani, J., Kodama, K., Kunimoto, K. & Hirayama, N. (2001). Anal. Sci. A17, 1471-1472.
Onimura, K., Matsushima, M., Yamabuki, K. & Oishi, T. (2010). Polym. J. 42, 290-297.
Sheldrick, G. M. (1998). SADABS. University of Göttingen, Germany.
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.
Shorunov, S. V., Krayushkin, M. M., Stoyanovich, F. M. & Irie, M. (2006). Russ. J. Org. Chem. 42, 1490-1497.

organic compounds