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Volume 69 
Part 6 
Pages o846-o847  
June 2013  

Received 22 April 2013
Accepted 26 April 2013
Online 11 May 2013

Key indicators
Single-crystal X-ray study
T = 150 K
Mean [sigma](C-C) = 0.004 Å
R = 0.054
wR = 0.098
Data-to-parameter ratio = 16.3
Details
Open access

2-(2,6-Dichlorophenyl)-1-pentyl-4,5-diphenyl-1H-imidazole

aDepartment of Physics, Faculty of Sciences, Erciyes University, 38039 Kayseri, Turkey,bChemistry and Environmental Division, Manchester Metropolitan University, Manchester M1 5GD, England,cChemistry Department, Faculty of Sccience, Mini University, 61519 El-Minia, Egypt,dDepartment of Chemistry, University of Leicester, Leicester, England, and ePharmaceutical Chemistry Department, Faculty of Pharmacy, Al Azhar University, Egypt
Correspondence e-mail: shaabankamel@yahoo.com

The title compound, C26H24Cl2N2, crystallizes with two independent molecules (1 and 2) in the asymmetric unit. In molecule 1, the two phenyl and 2,6-dichlorophenyl rings are inclined to the imidazole ring at angles of 74.12 (14), 26.13 (14) and 67.30 (14)°, respectively. In molecule 2, due to the different molecular environment in the crystal, the corresponding angles are different, viz. 71.72 (15), 16.14 (15) and 80.41 (15)°, respectively. In the crystal, molecules 1 and 2 are linked by C-H...Cl interactions, and inversion-related 2 molecules are linked by C-H...[pi] interactions. There are no other significant intermolecular interactions present.

Related literature

For some biological applications of imidazoles, see: Prabhu & Radha (2012[Prabhu, M. & Radha, R. (2012). Asian J. Pharm. Clin. Res. 5, 154-159.]); Sharma et al. (2009[Sharma, D., Narasimhan, B., Kumar, P., Judge, V., Narang, R., De Clercq, E. & Balzarini, J. (2009). Eur. J. Med. Chem. 44, 2347-2353.], 2010[Sharma, G. K., Kumar, S. & Pathak, D. (2010). Pharma Lett. 2, 223-230.]); Pandey et al. (2009[Pandey, J., Tiwari, V. K., Verma, S. S., Chaturvedi, V., Bhatnagar, S. & Sinha, S. (2009). Eur. J. Med. Chem. 44, 3350-3355.]); Sisko & Mellinger (2002[Sisko, J. & Mellinger, M. (2002). Pure Appl. Chem. 74, 1349-1357.]); Puratchikody & Doble (2007[Puratchikody, A. & Doble, M. (2007). Bioorg. Med. Chem. 15, 1083-1090.]). For the synthesis of imidazole-containing compounds and a similar structure, 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.]).

[Scheme 1]

Experimental

Crystal data
  • C26H24Cl2N2

  • Mr = 435.37

  • Monoclinic, P 21 /c

  • a = 20.172 (6) Å

  • b = 15.947 (5) Å

  • c = 14.500 (5) Å

  • [beta] = 105.293 (7)°

  • V = 4499 (2) Å3

  • Z = 8

  • Mo K[alpha] radiation

  • [mu] = 0.30 mm-1

  • T = 150 K

  • 0.34 × 0.16 × 0.11 mm

Data collection
  • Bruker APEX 2000 CCD area-detector diffractometer

  • Absorption correction: multi-scan (SADABS; Bruker, 2011[Bruker (2011). SMART, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.]) Tmin = 0.516, Tmax = 0.928

  • 34900 measured reflections

  • 8837 independent reflections

  • 5052 reflections with I > 2[sigma](I)

  • Rint = 0.123

Refinement
  • R[F2 > 2[sigma](F2)] = 0.054

  • wR(F2) = 0.098

  • S = 0.84

  • 8837 reflections

  • 543 parameters

  • H-atom parameters constrained

  • [Delta][rho]max = 0.29 e Å-3

  • [Delta][rho]min = -0.39 e Å-3

Table 1
Hydrogen-bond geometry (Å, °)

Cg1 is the centroid of the N1/N2/C1-C3 imidazole ring.

D-H...A D-H H...A D...A D-H...A
C12A-H12A...Cl1i 0.95 2.70 3.512 (4) 143
C21-H21...Cg1ii 0.95 2.88 3.734 (3) 151
Symmetry codes: (i) x, y, z+1; (ii) -x+1, -y, -z+1.

Data collection: SMART (Bruker, 2011[Bruker (2011). SMART, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.]); cell refinement: SAINT (Bruker, 2011[Bruker (2011). SMART, 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: SU2592 ).


Acknowledgements

The authors are grateful to Manchester Metropolitan University, the University of Leicester and Erciyes University for supporting this study.

References

Bruker (2011). SMART, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.
Farrugia, L. J. (2012). J. Appl. Cryst. 45, 849-854.  [ISI] [CrossRef] [ChemPort] [details]
Pandey, J., Tiwari, V. K., Verma, S. S., Chaturvedi, V., Bhatnagar, S. & Sinha, S. (2009). Eur. J. Med. Chem. 44, 3350-3355.  [ISI] [CrossRef] [PubMed] [ChemPort]
Prabhu, M. & Radha, R. (2012). Asian J. Pharm. Clin. Res. 5, 154-159.  [ChemPort]
Puratchikody, A. & Doble, M. (2007). Bioorg. Med. Chem. 15, 1083-1090.  [CrossRef] [PubMed] [ChemPort]
Sharma, G. K., Kumar, S. & Pathak, D. (2010). Pharma Lett. 2, 223-230.  [ChemPort]
Sharma, D., Narasimhan, B., Kumar, P., Judge, V., Narang, R., De Clercq, E. & Balzarini, J. (2009). Eur. J. Med. Chem. 44, 2347-2353.  [ISI] [CrossRef] [PubMed] [ChemPort]
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]
Sisko, J. & Mellinger, M. (2002). Pure Appl. Chem. 74, 1349-1357.  [ISI] [CrossRef] [ChemPort]
Spek, A. L. (2009). Acta Cryst. D65, 148-155.  [ISI] [CrossRef] [ChemPort] [details]


Acta Cryst (2013). E69, o846-o847   [ doi:10.1107/S1600536813011446 ]

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