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Volume 69 
Part 8 
Page o1243  
August 2013  

Received 24 May 2013
Accepted 1 July 2013
Online 13 July 2013

Key indicators
Single-crystal X-ray study
T = 150 K
Mean [sigma](C-C) = 0.003 Å
R = 0.053
wR = 0.110
Data-to-parameter ratio = 16.5
Details
Open access

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

aChemistry and Environmental Division, Manchester Metropolitan University, Manchester, M1 5GD, England,bChemistry Department, Faculty of Science, Mini 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 fChemistry Department, Faculty of Science, Sohag University, 82524 Sohag, Egypt
Correspondence e-mail: shaabankamel@yahoo.com

In the title compound, C26H25ClN2, the phenyl rings and the 2-(4-chlorophenyl) group make dihedral angles of 30.03 (11), 67.49 (12) and 41.56 (11)°, respectively, with the imidazole ring. In the crystal, the molecules interact with each other via very weak C-H...[pi] contacts, forming layers parallel to (110).

Related literature

For biological applications of imidazole derivatives, see: Shalini et al. (2011[Shalini, K., Kumar, N. & Sharma, P. K. (2011). Biointerface Res. Appl. Chem. 1, 184-190.]); Ramesh et al. (2012[Ramesh, K., Murthy, S. N., Karnakar, K., Nageswar, Y. V. D., Vijayalakhshmi, K., Devi, B. L. A. P. & Prasad, R. P. N. (2012). Tetrahedron Lett. 53, 1126-1129.]); Wolkenberg et al. (2004[Wolkenberg, S. E., Wisnoski, D. D., Leister, W. H., Wang, Y., Zhao, Z. & Lindsley, C. W. (2004). Org. Lett. 6, 1453-1456.]). For related structures, see: Simpson et al. (2013[Simpson, J., Mohamed, S. K., Marzouk, A. A., Talybov, A. H. & Abdelhamid, A. A. (2013). Acta Cryst. E69, o5-o6.]); Akkurt et al. (2013[Akkurt, M., Mohamed, S. K., Singh, K., Marzouk, A. A. & Abdelhamid, A. A. (2013). Acta Cryst. E69, o846-o847.]).

[Scheme 1]

Experimental

Crystal data
  • C26H25ClN2

  • Mr = 400.93

  • Monoclinic, P 21 /n

  • a = 10.471 (2) Å

  • b = 9.7798 (19) Å

  • c = 21.682 (4) Å

  • [beta] = 91.080 (4)°

  • V = 2219.9 (7) Å3

  • Z = 4

  • Mo K[alpha] radiation

  • [mu] = 0.19 mm-1

  • T = 150 K

  • 0.36 × 0.14 × 0.11 mm

Data collection
  • Bruker APEX 2000 CCD area-detector diffractometer

  • Absorption correction: multi-scan (SADABS; Bruker, 2001[Bruker (2001). SAINT, SMART and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.]) Tmin = 0.969, Tmax = 0.980

  • 16940 measured reflections

  • 4346 independent reflections

  • 2593 reflections with I > 2[sigma](I)

  • Rint = 0.088

Refinement
  • R[F2 > 2[sigma](F2)] = 0.053

  • wR(F2) = 0.110

  • S = 0.89

  • 4346 reflections

  • 263 parameters

  • H-atom parameters constrained

  • [Delta][rho]max = 0.26 e Å-3

  • [Delta][rho]min = -0.31 e Å-3

Table 1
Hydrogen-bond geometry (Å, °)

D-H...A D-H H...A D...A D-H...A
C20-H20...C25i 0.95 3.00 3.887 (3) 157
C24-H24...C13ii 0.95 2.78 3.697 (3) 163
C28-H28...N3iii 0.95 2.88 3.444 (3) 119
C28-H28...C17iii 0.95 3.00 3.894 (3) 158
Symmetry codes: (i) -x+3, -y, -z+2; (ii) -x+2, -y+1, -z+2; (iii) -x+2, -y, -z+2.

Data collection: SMART (Bruker, 2001[Bruker (2001). SAINT, SMART and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.]); cell refinement: SAINT (Bruker, 2001[Bruker (2001). SAINT, SMART 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: YK2095 ).


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] [IUCr Journals]
Bruker (2001). SAINT, SMART and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.
Farrugia, L. J. (2012). J. Appl. Cryst. 45, 849-854.  [Web of Science] [CrossRef] [ChemPort] [IUCr Journals]
Ramesh, K., Murthy, S. N., Karnakar, K., Nageswar, Y. V. D., Vijayalakhshmi, K., Devi, B. L. A. P. & Prasad, R. P. N. (2012). Tetrahedron Lett. 53, 1126-1129.  [Web of Science] [CrossRef] [ChemPort]
Shalini, K., Kumar, N. & Sharma, P. K. (2011). Biointerface Res. Appl. Chem. 1, 184-190.
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.  [CrossRef] [ChemPort] [IUCr Journals]
Simpson, J., Mohamed, S. K., Marzouk, A. A., Talybov, A. H. & Abdelhamid, A. A. (2013). Acta Cryst. E69, o5-o6.  [CSD] [CrossRef] [ChemPort] [IUCr Journals]
Spek, A. L. (2009). Acta Cryst. D65, 148-155.  [Web of Science] [CrossRef] [ChemPort] [IUCr Journals]
Wolkenberg, S. E., Wisnoski, D. D., Leister, W. H., Wang, Y., Zhao, Z. & Lindsley, C. W. (2004). Org. Lett. 6, 1453-1456.  [Web of Science] [CrossRef] [PubMed] [ChemPort]


Acta Cryst (2013). E69, o1243  [ doi:10.1107/S1600536813018229 ]

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