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Volume 69 
Part 9 
Page o1417  
September 2013  

Received 6 August 2013
Accepted 6 August 2013
Online 14 August 2013

Key indicators
Single-crystal X-ray study
T = 150 K
Mean [sigma](C-C) = 0.007 Å
R = 0.066
wR = 0.116
Data-to-parameter ratio = 16.5
Details
Open access

2-(4-Bromophenyl)-1-pentyl-4,5-diphenyl-1H-imidazole

aChemistry and Environmental Division, Manchester Metropolitan University, Manchester M1 5GD, England,bChemistry Department, Faculty of Science, Minia University, 61519 El-Minia, Egypt,cDepartment of Physics, Faculty of Sciences, Erciyes University, 38039 Kayseri, Turkey,dDepartment of Chemistry, University of Leicester, Leicester, England,ePharmaceutical Chemistry Department, Faculty of Pharmacy, Al Azhar University, Egypt, and fKirkuk University, College of Science, Department of Chemistry, Kirkuk, Iraq
Correspondence e-mail: shaabankamel@yahoo.com

The title compound, C26H25BrN2, is isomorphous with the chloro derivative [2-(4-chlorophenyl)-1-pentyl-4,5-diphenyl-1H-imidazole; Mohamed et al. (2013[Mohamed, S. K., Akkurt, M., Singh, K., Marzouk, A. A. & Abdelhamid, A. A. (2013). Acta Cryst. E69, o1243.]). Acta Cryst. E69, o846-o847]. The two phenyl rings and the 4-bromophenyl ring are oriented at dihedral angles of 30.1 (2), 64.3 (3) and 42.0 (2)°, respectively, with respect to the imidazole ring. In the crystal, molecules stack in columns along the b-axis direction, however, there are no significant intermolecular interactions present.

Related literature

For biological and synthetic applications of imidazole derivatives, see: Maier et al. (1989a[Maier, T., Schmierer, R., Bauer, K., Bieringer, H., Buerstell, H. & Sachse, B. (1989a). US Patent 4820335.],b[Maier, T., Schmierer, R., Bauer, K., Bieringer, H., Buerstell, H. & Sachse, B. (1989b). Chem. Abstr. 111, 19494.]); Welton (1999[Welton, T. (1999). Chem. Rev. 99, 2071-2084.]); Hermann & Kocher (1997[Hermann, W. A. & Kocher, C. (1997). Angew. Chem. Int. Ed. Engl. 36, 2162-2187.]). For related structures, see: Akkurt et al. (2013[Akkurt, M., Mohamed, S. K., Singh, K., Marzouk, A. A. & Abdelhamid, A. A. (2013). Acta Cryst. E69, o846-o847.]); Mohamed et al. (2013[Mohamed, S. K., Akkurt, M., Singh, K., Marzouk, A. A. & Abdelhamid, A. A. (2013). Acta Cryst. E69, o1243.]); Simpson et al. (2013[Simpson, J., Mohamed, S. K., Marzouk, A. A., Talybov, A. H. & Abdelhamid, A. A. (2013). Acta Cryst. E69, o5-o6.]).

[Scheme 1]

Experimental

Crystal data
  • C26H25BrN2

  • Mr = 445.39

  • Monoclinic, P 21 /n

  • a = 10.665 (5) Å

  • b = 9.619 (5) Å

  • c = 21.541 (10) Å

  • [beta] = 91.092 (9)°

  • V = 2209.4 (19) Å3

  • Z = 4

  • Mo K[alpha] radiation

  • [mu] = 1.88 mm-1

  • T = 150 K

  • 0.36 × 0.16 × 0.03 mm

Data collection
  • Bruker APEXII CCD area-detector diffractometer

  • Absorption correction: multi-scan (SADABS; Bruker, 2011[Bruker (2011). APEX2, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.]) Tmin = 0.600, Tmax = 0.969

  • 16966 measured reflections

  • 4329 independent reflections

  • 2328 reflections with I > 2[sigma](I)

  • Rint = 0.187

Refinement
  • R[F2 > 2[sigma](F2)] = 0.066

  • wR(F2) = 0.116

  • S = 0.88

  • 4329 reflections

  • 263 parameters

  • H-atom parameters constrained

  • [Delta][rho]max = 0.61 e Å-3

  • [Delta][rho]min = -1.05 e Å-3

Data collection: APEX2 (Bruker, 2011[Bruker (2011). APEX2, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.]); cell refinement: SAINT (Bruker, 2011[Bruker (2011). APEX2, SAINT and SADABS. 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: ORTEP-3 for Windows (Farrugia, 2012[Farrugia, L. J. (2012). J. Appl. Cryst. 45, 849-854.]); software used to prepare material for publication: WinGX (Farrugia, 2012[Farrugia, L. J. (2012). J. Appl. Cryst. 45, 849-854.]) and PLATON (Spek, 2009[Spek, A. L. (2009). Acta Cryst. D65, 148-155.]).


Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: SU2633 ).


Acknowledgements

Manchester Metropolitan University, Erciyes University and the University of Leicester are gratefully acknowledged for supporting this study.

References

Akkurt, M., Mohamed, S. K., Singh, K., Marzouk, A. A. & Abdelhamid, A. A. (2013). Acta Cryst. E69, o846-o847.  [CSD] [CrossRef] [ChemPort] [details]
Bruker (2011). APEX2, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.
Farrugia, L. J. (2012). J. Appl. Cryst. 45, 849-854.  [ISI] [CrossRef] [ChemPort] [details]
Hermann, W. A. & Kocher, C. (1997). Angew. Chem. Int. Ed. Engl. 36, 2162-2187.  [CrossRef] [ISI]
Maier, T., Schmierer, R., Bauer, K., Bieringer, H., Buerstell, H. & Sachse, B. (1989a). US Patent 4820335.
Maier, T., Schmierer, R., Bauer, K., Bieringer, H., Buerstell, H. & Sachse, B. (1989b). Chem. Abstr. 111, 19494.
Mohamed, S. K., Akkurt, M., Singh, K., Marzouk, A. A. & Abdelhamid, A. A. (2013). Acta Cryst. E69, o1243.  [CrossRef] [details]
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.  [CrossRef] [ChemPort] [details]
Simpson, J., Mohamed, S. K., Marzouk, A. A., Talybov, A. H. & Abdelhamid, A. A. (2013). Acta Cryst. E69, o5-o6.  [CSD] [CrossRef] [ChemPort] [details]
Spek, A. L. (2009). Acta Cryst. D65, 148-155.  [ISI] [CrossRef] [ChemPort] [details]
Welton, T. (1999). Chem. Rev. 99, 2071-2084.  [ISI] [CrossRef] [PubMed] [ChemPort]


Acta Cryst (2013). E69, o1417  [ doi:10.1107/S1600536813021983 ]

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