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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 [sigma](C-C) = 0.011 Å
R = 0.050
wR = 0.133
Data-to-parameter ratio = 13.9
Details
Open access

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

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-H...O 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[Fujii, I., Ohtani, J., Kodama, K., Kunimoto, K. & Hirayama, N. (2001). Anal. Sci. A17, 1471-1472.]); Onimura et al. (2010[Onimura, K., Matsushima, M., Yamabuki, K. & Oishi, T. (2010). Polym. J. 42, 290-297.]); Shorunov et al. (2006[Shorunov, S. V., Krayushkin, M. M., Stoyanovich, F. M. & Irie, M. (2006). Russ. J. Org. Chem. 42, 1490-1497.]).

[Scheme 1]

Experimental

Crystal data
  • C22H13Br2NO2

  • Mr = 483.13

  • Monoclinic, P 21 /c

  • a = 10.844 (5) Å

  • b = 18.594 (9) Å

  • c = 9.602 (5) Å

  • [beta] = 102.760 (6)°

  • V = 1888.3 (16) Å3

  • Z = 4

  • Mo K[alpha] radiation

  • [mu] = 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[Sheldrick, G. M. (1998). SADABS. University of Göttingen, Germany.]) Tmin = 0.339, Tmax = 0.424

  • 8594 measured reflections

  • 3382 independent reflections

  • 1427 reflections with I > 2[sigma](I)

  • Rint = 0.117

Refinement
  • R[F2 > 2[sigma](F2)] = 0.050

  • wR(F2) = 0.133

  • S = 0.94

  • 3382 reflections

  • 244 parameters

  • H-atom parameters constrained

  • [Delta][rho]max = 0.51 e Å-3

  • [Delta][rho]min = -0.71 e Å-3

Table 1
Hydrogen-bond geometry (Å, °)

D-H...A D-H H...A D...A D-H...A
C21-H21...O1i 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[Bruker (2005). APEX2. Bruker AXS Inc., Madison, Wisconsin, USA.]); cell refinement: SAINT (Bruker, 2001[Bruker (2001). 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: SHELXTL (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); 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.  [ChemPort]
Sheldrick, G. M. (1998). SADABS. University of Göttingen, Germany.
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.  [CrossRef] [details]
Shorunov, S. V., Krayushkin, M. M., Stoyanovich, F. M. & Irie, M. (2006). Russ. J. Org. Chem. 42, 1490-1497.  [ChemPort]


Acta Cryst (2011). E67, o1198  [ doi:10.1107/S1600536811014152 ]

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