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Volume 69 
Part 12 
Pages o1833-o1834  
December 2013  

Received 20 November 2013
Accepted 21 November 2013
Online 27 November 2013

Key indicators
Single-crystal X-ray study
T = 150 K
Mean [sigma](C-C) = 0.004 Å
R = 0.058
wR = 0.127
Data-to-parameter ratio = 13.5
Details
Open access

2-(3,4-Di­meth­oxy­phen­yl)-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,dPharmaceutical Chemistry Department, Faculty of Pharmacy, Al Azhar University, Egypt,eDepartment of Chemistry, University of Leicester, Leicester, England, and fKirkuk University, College of Science, Department of Chemistry, Kirkuk, Iraq
Correspondence e-mail: shaabankamel@yahoo.com

The central imidazole ring in the title compound, C28H30N2O2, makes dihedral angles of 28.42 (13), 71.22 (15) and 29.50 (14)°, respectively, with the phenyl rings in the 4- and 5-positions and the 3,4-di­meth­oxy­phenyl group. In the crystal, mol­ecules are linked by C-H...O and C-H...N hydrogen bonds, weak [pi]-[pi] stacking inter­actions [centroid-centroid distance = 3.760 (2) Å] and C-H...[pi] contacts, forming a three-dimensional network.

Related literature

For medicinal and industrial applications of imidazole-containing compounds see: Oyeka & Gugnani (1992[Oyeka, C. A. & Gugnani, H. C. (1992). Mycoses, 35, 357-61.]); Schrekker et al. (2013[Schrekker, H. S., Donato, R. K., Fuentefri, A. M., Bergamo, V., Oliveira, L. F. & Machado, M. M. (2013). MedChemComm, 4, 1457-1460.]); Mital (2009[Mital, A. (2009). Sci. Pharm. 77, 497-520.]); Juchau (1989[Juchau, M. R. (1989). Annu. Rev. Pharmacol. Toxicol. 29, 165-167.]); Rondu et al. (1997[Rondu, F., Le Bihan, G., Wang, X., Lamouri, A., Touboul, E., Dive, G., Bellahsene, T., Pfeiffer, B., Renard, P., Guardiola-L, B., Manechez, D., Penicaud, L., Ktorza, A. & Godfroid, J. J. (1997). J. Med. Chem. 40, 3793-3803.]); Bousquet & Feldman (1999[Bousquet, P. & Feldman, J. (1999). Drugs, 58, 799-812.]); Ueno et al. (1995[Ueno, M., Imaizumi, K., Sugita, T., Takata, I. & Takeshita, M. (1995). Int. J. Immunopharmacol. 17, 597-603.]); Jung & Huang (2000[Jung, M. E. & Huang, A. (2000). Org. Lett. 2, 2659-2661.]); Isobe et al. (2001[Isobe, T., Fukuda, K., Araki, Y. & Ishikawa, T. (2001). Chem. Commun. pp. 243-244.]). For similar 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. & Albayati, M. R. (2013). Acta Cryst. E69, o1417.]).

[Scheme 1]

Experimental

Crystal data
  • C28H30N2O2

  • Mr = 426.54

  • Triclinic, [P \overline 1]

  • a = 8.900 (2) Å

  • b = 11.915 (3) Å

  • c = 12.009 (3) Å

  • [alpha] = 106.757 (6)°

  • [beta] = 96.007 (5)°

  • [gamma] = 108.170 (6)°

  • V = 1131.8 (5) Å3

  • Z = 2

  • Mo K[alpha] radiation

  • [mu] = 0.08 mm-1

  • T = 150 K

  • 0.24 × 0.21 × 0.11 mm

Data collection
  • Bruker APEX2000 CCD area-detector diffractometer

  • Absorption correction: multi-scan (SADABS; Bruker, 2011[Bruker (2011). SMART, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.]) Tmin = 0.668, Tmax = 0.981

  • 8350 measured reflections

  • 3953 independent reflections

  • 2219 reflections with I > 2[sigma](I)

  • Rint = 0.086

Refinement
  • R[F2 > 2[sigma](F2)] = 0.058

  • wR(F2) = 0.127

  • S = 0.87

  • 3953 reflections

  • 292 parameters

  • H-atom parameters constrained

  • [Delta][rho]max = 0.25 e Å-3

  • [Delta][rho]min = -0.25 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
C23-H23...O1i 0.95 2.53 3.168 (4) 125
C27-H27A...N2ii 0.98 2.51 3.474 (3) 168
C27-H27A...Cg1ii 0.98 2.77 3.608 (3) 144
Symmetry codes: (i) x-1, y-1, z-1; (ii) -x+2, -y+2, -z+2.

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: SJ5371 ).


Acknowledgements

Manchester Metropolitan University, Erciyes University and Alazhar University 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]
Bousquet, P. & Feldman, J. (1999). Drugs, 58, 799-812.  [Web of Science] [CrossRef] [PubMed] [ChemPort]
Bruker (2011). SMART, SAINT 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]
Isobe, T., Fukuda, K., Araki, Y. & Ishikawa, T. (2001). Chem. Commun. pp. 243-244.  [CrossRef]
Juchau, M. R. (1989). Annu. Rev. Pharmacol. Toxicol. 29, 165-167.  [CrossRef] [ChemPort] [PubMed]
Jung, M. E. & Huang, A. (2000). Org. Lett. 2, 2659-2661.  [Web of Science] [CrossRef] [PubMed] [ChemPort]
Mital, A. (2009). Sci. Pharm. 77, 497-520.  [CrossRef] [ChemPort]
Mohamed, S. K., Akkurt, M., Singh, K., Marzouk, A. A. & Albayati, M. R. (2013). Acta Cryst. E69, o1417.  [CSD] [CrossRef] [IUCr Journals]
Oyeka, C. A. & Gugnani, H. C. (1992). Mycoses, 35, 357-61.  [CrossRef] [PubMed] [ChemPort]
Rondu, F., Le Bihan, G., Wang, X., Lamouri, A., Touboul, E., Dive, G., Bellahsene, T., Pfeiffer, B., Renard, P., Guardiola-L, B., Manechez, D., Penicaud, L., Ktorza, A. & Godfroid, J. J. (1997). J. Med. Chem. 40, 3793-3803.  [CrossRef] [ChemPort] [PubMed] [Web of Science]
Schrekker, H. S., Donato, R. K., Fuentefri, A. M., Bergamo, V., Oliveira, L. F. & Machado, M. M. (2013). MedChemComm, 4, 1457-1460.  [CrossRef] [ChemPort]
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.  [CrossRef] [ChemPort] [IUCr Journals]
Spek, A. L. (2009). Acta Cryst. D65, 148-155.  [Web of Science] [CrossRef] [ChemPort] [IUCr Journals]
Ueno, M., Imaizumi, K., Sugita, T., Takata, I. & Takeshita, M. (1995). Int. J. Immunopharmacol. 17, 597-603.  [CrossRef] [ChemPort] [PubMed] [Web of Science]


Acta Cryst (2013). E69, o1833-o1834   [ doi:10.1107/S1600536813031759 ]

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