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Volume 69 
Part 6 
Pages o988-o989  
June 2013  

Received 15 May 2013
Accepted 21 May 2013
Online 31 May 2013

Key indicators
Single-crystal X-ray study
T = 100 K
Mean [sigma](C-C) = 0.003 Å
Disorder in main residue
R = 0.062
wR = 0.183
Data-to-parameter ratio = 10.6
Details
Open access

2,4,5-Triphenyl-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, and fDepartment 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, C24H20N2, one of the ring C atoms and one of the ring N atoms are disordered over two sets of sites in a 0.615 (3):0.385 (3) ratio. The two parts of the disordered imidazole ring adopt an envelope conformation, with the undisordered ring N atom as the flap, displaced by -0.118 (6) and 0.226 (7) Å, respectively, in the two disorder components from the plane through the other ring atoms. The crystal structure features C-H...N hydrogen bonds and C-H...[pi] interactions, which lead to the formation of infinite chains along [010].

Related literature

For the biological significance of imidazole derivatives, see, for example: Kumar (2010[Kumar, J. R. (2010). Pharmacophore, 1, 167-177.]); Castaño et al. (2008[Castaño, T., Encinas, A., Pérez, C., Castro, A., Campillo, N. E. & Gil, C. (2008). Bioorg. Med. Chem. 16, 6193-6206.]); Banfi et al. (2006[Banfi, E., Scialino, G., Zampieri, D., Mamolo, M. G., Vio, L., Ferrone, M., Maurizio Fermeglia, M., Paneni, M. S. & Sabrina Pric, S. (2006). J. Antimicrob. Chemother. 58, 76-84.]); Bogle et al. (1994[Bogle, R. G., Whitley, G. S., Soo, S. C., Johnstone, A. P. & Vallance, P. (1994). Br. J. Pharmacol. 111, 1257-1261.]). For the synthesis and the structures of similar imidazoles, see: 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.]); Akkurt et al. (2013[Akkurt, M., Fronczek, F. R., Mohamed, S. K., Talybov, A. H., Marzouk, A. A. E. & Abdelhamid, A. A. (2013). Acta Cryst. E69, o527-o528.]). For puckering parameters, see: Cremer & Pople (1975[Cremer, D. & Pople, J. A. (1975). J. Am. Chem. Soc. 97, 1354-1358.]).

[Scheme 1]

Experimental

Crystal data
  • C24H20N2

  • Mr = 336.42

  • Monoclinic, P 21 /n

  • a = 10.362 (3) Å

  • b = 8.938 (2) Å

  • c = 19.387 (5) Å

  • [beta] = 90.340 (5)°

  • V = 1795.5 (8) Å3

  • Z = 4

  • Mo K[alpha] radiation

  • [mu] = 0.07 mm-1

  • T = 100 K

  • 0.14 × 0.14 × 0.003 mm

Data collection
  • Bruker SMART APEX CCD area-detector diffractometer

  • Absorption correction: refined from [Delta]F (XABS2; Parkin et al., 1995[Parkin, S., Moezzi, B. & Hope, H. (1995). J. Appl. Cryst. 28, 53-56.]) Tmin = 0.990, Tmax = 1.000

  • 17127 measured reflections

  • 3168 independent reflections

  • 2442 reflections with I > 2[sigma](I)

  • Rint = 0.046

Refinement
  • R[F2 > 2[sigma](F2)] = 0.062

  • wR(F2) = 0.183

  • S = 1.04

  • 3168 reflections

  • 299 parameters

  • 12 restraints

  • H-atom parameters constrained

  • [Delta][rho]max = 0.49 e Å-3

  • [Delta][rho]min = -0.29 e Å-3

Table 1
Hydrogen-bond geometry (Å, °)

Cg3 and Cg4 are the centroids of the C4-C9 and C10-C15 rings, respectively.

D-H...A D-H H...A D...A D-H...A
C17A-H17A...N1i 0.95 2.45 3.246 (8) 141
C21A-H21A...Cg3ii 0.95 2.98 3.888 (5) 160
C21B-H21B...Cg4i 0.95 2.99 3.914 (4) 163
Symmetry codes: (i) -x, -y+2, -z+1; (ii) -x, -y+1, -z+1.

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: ZP2005 ).


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. (2013). Acta Cryst. E69, o527-o528.  [CrossRef] [ChemPort] [details]
Banfi, E., Scialino, G., Zampieri, D., Mamolo, M. G., Vio, L., Ferrone, M., Maurizio Fermeglia, M., Paneni, M. S. & Sabrina Pric, S. (2006). J. Antimicrob. Chemother. 58, 76-84.  [CrossRef] [PubMed] [ChemPort]
Bogle, R. G., Whitley, G. S., Soo, S. C., Johnstone, A. P. & Vallance, P. (1994). Br. J. Pharmacol. 111, 1257-1261.  [CrossRef] [ChemPort] [PubMed]
Bruker (2001). SMART and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.
Castaño, T., Encinas, A., Pérez, C., Castro, A., Campillo, N. E. & Gil, C. (2008). Bioorg. Med. Chem. 16, 6193-6206.  [PubMed]
Cremer, D. & Pople, J. A. (1975). J. Am. Chem. Soc. 97, 1354-1358.  [CrossRef] [ChemPort] [ISI]
Farrugia, L. J. (2012). J. Appl. Cryst. 45, 849-854.  [ISI] [CrossRef] [ChemPort] [details]
Kumar, J. R. (2010). Pharmacophore, 1, 167-177.  [ChemPort]
Mohamed, S. K., Akkurt, M., Marzouk, A. A., Abbasov, V. M. & Gurbanov, A. V. (2013a). Acta Cryst. E69, o474-o475.  [CrossRef] [ChemPort] [details]
Mohamed, S. K., Akkurt, M., Marzouk, A. A. E., Santoyo-Gonzalez, F. & Elremaily, M. A. A. (2013b). Acta Cryst. E69, o875-o876.  [CrossRef] [details]
Parkin, S., Moezzi, B. & Hope, H. (1995). J. Appl. Cryst. 28, 53-56.  [CrossRef] [ChemPort] [ISI] [details]
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.  [CrossRef] [ChemPort] [details]
Spek, A. L. (2009). Acta Cryst. D65, 148-155.  [ISI] [CrossRef] [ChemPort] [details]


Acta Cryst (2013). E69, o988-o989   [ doi:10.1107/S1600536813014104 ]

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