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Volume 69 
Part 7 
Pages o1098-o1099  
July 2013  

Received 3 June 2013
Accepted 7 June 2013
Online 15 June 2013

Key indicators
Single-crystal X-ray study
T = 100 K
Mean [sigma](C-C) = 0.003 Å
R = 0.047
wR = 0.125
Data-to-parameter ratio = 15.4
Details
Open access

2-(2,5-Dimethoxyphenyl)-4,5-diphenyl-1-(prop-2-en-1-yl)-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 Science, Mini University, 61519 El-Minia, Egypt,dPharmaceutical Chemistry Department, Faculty of Pharmacy, Al Azhar University, Egypt,eMamedaliev Institute of Petrochemical Processes, National Academy of Sciences of Azerbaijan, Baku, Azerbaijan,fChemistry Department, Faculty of Science, Sohag University, 82524 Sohag, Egypt, and gDepartment of Organic Chemistry, Faculty of Science, Institute of Biotechnology, Granada University, Granada, E-18071, Spain
Correspondence e-mail: shaabankamel@yahoo.com

In the title compound, C26H24N2O2, the two phenyl and the 2,5-dimethoxyphenyl rings are inclined to the imidazole ring at dihedral angles of 30.38 (8), 56.59 (9) and 73.11 (9)°, respectively. In the crystal, molecules are linked by pairs of C-H...O interactions into centrosymmetric dimers with graph-set notation R22(8). C-H...[pi] interactions are also observed.

Related literature

For chemical properties and applications of imidazoles with an unsaturated side chain, see, for example: Koszykowska et al. (2009[Koszykowska, M., Tokarek, M. & Kucharski, S. (2009). Mater. Sci. Pol. 27, 699-708.]); Berezin et al. (2009[Berezin, M. Y., Jeff, K. & Achilefu, S. (2009). Chemistry, 15, 3560-3566.]); Rambo et al. (2010[Rambo, B. M., Silver, E. S., Bielawski, C. W. & Sessler, J. L. (2010). Heterocycl. Chem. 1, 1-37.]); Min et al. (2006[Min, G.-H., Yim, T., Lee, H. Y., Huh, D. H., Lee, E., Mun, J., Oh, S. M. & Kim, Y. G. (2006). Bull. Korean Chem. Soc. 27, 847-852.]). For similar structures, see: Akkurt et al. (2013a[Akkurt, M., Fronczek, F. R., Mohamed, S. K., Talybov, A. H., Marzouk, A. A. E. & Abdelhamid, A. A. (2013a). Acta Cryst. E69, o527-o528.],b[Akkurt, M., Mohamed, S. K., Singh, K., Marzouk, A. A. & Abdelhamid, A. A. (2013b). Acta Cryst. E69, o846-o847.]); Mohamed et al. (2013a[Mohamed, S. K., Akkurt, M., Marzouk, A. A., Abbasov, V. M. & Gurbanov, A. V. (2013a). Acta Cryst. E69, o474-o475.],b[Mohamed, S. K., Akkurt, M., Marzouk, A. A. E., Santoyo-Gonzalez, F. & Elremaily, M. A. A. (2013b). Acta Cryst. E69, o875-o876.]). For hydrogen-bond motifs, see: Bernstein et al. (1995[Bernstein, J., Davis, R. E., Shimoni, L. & Chang, N.-L. (1995). Angew. Chem. Int. Ed. Engl. 34, 1555-1573.]).

[Scheme 1]

Experimental

Crystal data
  • C26H24N2O2

  • Mr = 396.47

  • Triclinic, [P \overline 1]

  • a = 8.3117 (14) Å

  • b = 10.5217 (17) Å

  • c = 13.425 (2) Å

  • [alpha] = 105.938 (2)°

  • [beta] = 101.846 (2)°

  • [gamma] = 107.772 (2)°

  • V = 1020.1 (3) Å3

  • Z = 2

  • Mo K[alpha] radiation

  • [mu] = 0.08 mm-1

  • T = 100 K

  • 0.26 × 0.16 × 0.08 mm

Data collection
  • Bruker SMART APEX CCD area-detector diffractometer

  • Absorption correction: multi-scan (SADABS; Sheldrick, 2004[Sheldrick, G. M. (2004). SADABS. University of Göttingen, Germany.]) Tmin = 0.979, Tmax = 0.993

  • 11527 measured reflections

  • 4193 independent reflections

  • 3184 reflections with I > 2[sigma](I)

  • Rint = 0.036

Refinement
  • R[F2 > 2[sigma](F2)] = 0.047

  • wR(F2) = 0.125

  • S = 1.05

  • 4193 reflections

  • 273 parameters

  • H-atom parameters constrained

  • [Delta][rho]max = 0.23 e Å-3

  • [Delta][rho]min = -0.26 e Å-3

Table 1
Hydrogen-bond geometry (Å, °)

Cg1, Cg2 and Cg4 are the centroids of the N1/N2/C1-C3, C4-C9 and C19-C24 rings, respectively.

D-H...A D-H H...A D...A D-H...A
C20-H20...O1i 0.95 2.54 3.354 (2) 143
C14-H14...Cg2ii 0.95 2.63 3.4083 (19) 139
C25-H25B...Cg1iii 0.98 2.84 3.6337 (19) 139
C26-H26C...Cg4iv 0.98 2.95 3.908 (2) 166
Symmetry codes: (i) -x, -y+1, -z; (ii) -x, -y, -z+1; (iii) -x+1, -y+1, -z+1; (iv) -x+1, -y+1, -z.

Data collection: SMART (Bruker, 2001[Bruker (2001). SMART and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.]); cell refinement: SAINT (Bruker, 2001[Bruker (2001). SMART and 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: 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: BX2444 ).


Acknowledgements

Manchester Metropolitan University, Erciyes University and Granada University are gratefully acknowledged for supporting this study. The authors also thank José Romero Garzón, Centro de Instrumentación Científica, Universidad de Granada, for the data collection.

References

Akkurt, M., Fronczek, F. R., Mohamed, S. K., Talybov, A. H., Marzouk, A. A. E. & Abdelhamid, A. A. (2013a). Acta Cryst. E69, o527-o528.  [CrossRef] [ChemPort] [IUCr Journals]
Akkurt, M., Mohamed, S. K., Singh, K., Marzouk, A. A. & Abdelhamid, A. A. (2013b). Acta Cryst. E69, o846-o847.  [CrossRef] [ChemPort] [IUCr Journals]
Berezin, M. Y., Jeff, K. & Achilefu, S. (2009). Chemistry, 15, 3560-3566.  [PubMed] [ChemPort]
Bernstein, J., Davis, R. E., Shimoni, L. & Chang, N.-L. (1995). Angew. Chem. Int. Ed. Engl. 34, 1555-1573.  [CrossRef] [ChemPort] [Web of Science]
Bruker (2001). SMART and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.
Farrugia, L. J. (2012). J. Appl. Cryst. 45, 849-854.  [Web of Science] [CrossRef] [ChemPort] [IUCr Journals]
Koszykowska, M., Tokarek, M. & Kucharski, S. (2009). Mater. Sci. Pol. 27, 699-708.  [ChemPort]
Min, G.-H., Yim, T., Lee, H. Y., Huh, D. H., Lee, E., Mun, J., Oh, S. M. & Kim, Y. G. (2006). Bull. Korean Chem. Soc. 27, 847-852.  [ChemPort]
Mohamed, S. K., Akkurt, M., Marzouk, A. A., Abbasov, V. M. & Gurbanov, A. V. (2013a). Acta Cryst. E69, o474-o475.  [CrossRef] [ChemPort] [IUCr Journals]
Mohamed, S. K., Akkurt, M., Marzouk, A. A. E., Santoyo-Gonzalez, F. & Elremaily, M. A. A. (2013b). Acta Cryst. E69, o875-o876.  [CrossRef] [ChemPort] [IUCr Journals]
Rambo, B. M., Silver, E. S., Bielawski, C. W. & Sessler, J. L. (2010). Heterocycl. Chem. 1, 1-37.
Sheldrick, G. M. (2004). SADABS. University of Göttingen, Germany.
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]


Acta Cryst (2013). E69, o1098-o1099   [ doi:10.1107/S1600536813015936 ]

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