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Volume 69 
Part 6 
Pages o875-o876  
June 2013  

Received 7 May 2013
Accepted 8 May 2013
Online 11 May 2013

Key indicators
Single-crystal X-ray study
T = 100 K
Mean [sigma](C-C) = 0.002 Å
R = 0.041
wR = 0.106
Data-to-parameter ratio = 15.8
Details
Open access

2-(4-Chlorophenyl)-4,5-diphenyl-1-(prop-2-en-1-yl)-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,dPharmaceutical Chemistry Department, Faculty of Pharmacy, Al Azhar University, Egypt,eDepartment of Organic Chemistry, Faculty of Science, Institute of Biotechnology, Granada University, Granada, E-18071, Spain, and fChemistry Department, Faculty of Science, Sohag University, 82524 Shag, Egypt
Correspondence e-mail: shaabankamel@yahoo.com

The title compound, C24H19ClN2, crystallizes with two independent molecules in the asymmetric unit. The prop-2-enyl substituents on the imidazole rings adopt similar conformations in the two molecules. The 4-and 5-substituted phenyl rings and the benzene ring make dihedral angles of 67.06 (8), 5.61 (8) and 41.09 (8)°, respectively, with the imadazole ring in one molecule and 71.53 (8), 28.85 (8) and 41.87 (8)°, respectively, in the other. The crystal structure features C-H...[pi] interactions and weak [pi]-[pi] stacking interactions [centroid-centroid distances = 3.6937 (10) and 4.0232 (10) Å] between the chlorophenyl rings, which form a three-dimensional supramolecular structure.

Related literature

For pharmaceutical properties of imidazoles and imidazole-containing compounds, see, for example: Roman et al. (2007[Roman, G., Riley, J. G., Vlahakis, J. Z., Kinobe, R. T., Brien, J. F., Nakatsu, K. & Szarek, W. A. (2007). Bioorg. Med. Chem. 15, 3225-3234.]); Nanterment et al. (2004[Nanterment, P. G., Barrow, J. C., Lindsley, S. R., Young, M., Mao, S., Carroll, S., Bailey, C., Bosserman, M., Colussi, D., McMasters, D. R., Vacca, J. P. & Selnick, H. G. (2004). Bioorg. Med. Chem. Lett. 14, 2141-2145.]); Congiu et al. (2008[Congiu, C., Cocco, M. T. & Onnis, V. (2008). Bioorg. Med. Chem. Lett. 18, 989-993.]); Venkatesan et al. (2008[Venkatesan, A. M., Agarwal, A., Abe, T., Ushirogochi, H. O., Santos, D., Li, Z., Francisco, G., Lin, Y. I., Peterson, P. J., Yang, Y., Weiss, W. J., Shales, D. M. & Mansour, T. S. (2008). Bioorg. Med. Chem. 16, 1890-1902.]); Bhatnagar et al. (2011[Bhatnagar, A., Sharma, P. K. & Kumar, N. (2011). Int. J. Pharm. Tech. Res. 3, 268-282.]); Puratchikody & Doble (2007[Puratchikody, A. & Doble, M. (2007). Bioorg. Med. Chem. Lett. 15, 1083-1090.]). For similar structures, see: Mohamed et al. (2013[Mohamed, S. K., Akkurt, M., Marzouk, A. A., Abbasov, V. M. & Gurbanov, A. V. (2013). Acta Cryst. E69, o474-o475.]); 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.]).

[Scheme 1]

Experimental

Crystal data
  • C24H19ClN2

  • Mr = 370.86

  • Triclinic, [P \overline 1]

  • a = 10.0916 (7) Å

  • b = 13.1386 (9) Å

  • c = 15.6155 (10) Å

  • [alpha] = 72.924 (1)°

  • [beta] = 86.849 (1)°

  • [gamma] = 71.830 (1)°

  • V = 1879.0 (2) Å3

  • Z = 4

  • Mo K[alpha] radiation

  • [mu] = 0.21 mm-1

  • T = 100 K

  • 0.57 × 0.33 × 0.28 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 = 0.919, Tmax = 0.942

  • 20791 measured reflections

  • 7718 independent reflections

  • 6764 reflections with I > 2[sigma](I)

  • Rint = 0.023

Refinement
  • R[F2 > 2[sigma](F2)] = 0.041

  • wR(F2) = 0.106

  • S = 1.07

  • 7718 reflections

  • 487 parameters

  • H-atom parameters constrained

  • [Delta][rho]max = 0.34 e Å-3

  • [Delta][rho]min = -0.23 e Å-3

Table 1
Hydrogen-bond geometry (Å, °)

Cg2, Cg4 and Cg8 are the centroids of the C4-C9, C19-C24 and C43-C48 rings, respectively.

D-H...A D-H H...A D...A D-H...A
C5-H5...Cg4i 0.95 2.76 3.5968 (17) 147
C11-H11...Cg8ii 0.95 2.83 3.5879 (19) 137
C33-H33...Cg2iii 0.95 2.89 3.8217 (18) 166
Symmetry codes: (i) -x, -y+1, -z; (ii) -x, -y, -z+1; (iii) x, y, 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: HG5314 ).


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]
Bhatnagar, A., Sharma, P. K. & Kumar, N. (2011). Int. J. Pharm. Tech. Res. 3, 268-282.  [ChemPort]
Bruker (2001). SMART and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.
Congiu, C., Cocco, M. T. & Onnis, V. (2008). Bioorg. Med. Chem. Lett. 18, 989-993.  [CrossRef] [PubMed] [ChemPort]
Farrugia, L. J. (2012). J. Appl. Cryst. 45, 849-854.  [ISI] [CrossRef] [ChemPort] [details]
Mohamed, S. K., Akkurt, M., Marzouk, A. A., Abbasov, V. M. & Gurbanov, A. V. (2013). Acta Cryst. E69, o474-o475.  [CrossRef] [ChemPort] [details]
Nanterment, P. G., Barrow, J. C., Lindsley, S. R., Young, M., Mao, S., Carroll, S., Bailey, C., Bosserman, M., Colussi, D., McMasters, D. R., Vacca, J. P. & Selnick, H. G. (2004). Bioorg. Med. Chem. Lett. 14, 2141-2145.  [PubMed]
Puratchikody, A. & Doble, M. (2007). Bioorg. Med. Chem. Lett. 15, 1083-1090.  [ChemPort]
Roman, G., Riley, J. G., Vlahakis, J. Z., Kinobe, R. T., Brien, J. F., Nakatsu, K. & Szarek, W. A. (2007). Bioorg. Med. Chem. 15, 3225-3234.  [CrossRef] [PubMed] [ChemPort]
Sheldrick, G. M. (2004). SADABS. University of Göttingen, Germany.
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]
Venkatesan, A. M., Agarwal, A., Abe, T., Ushirogochi, H. O., Santos, D., Li, Z., Francisco, G., Lin, Y. I., Peterson, P. J., Yang, Y., Weiss, W. J., Shales, D. M. & Mansour, T. S. (2008). Bioorg. Med. Chem. 16, 1890-1902.  [CrossRef] [PubMed] [ChemPort]


Acta Cryst (2013). E69, o875-o876   [ doi:10.1107/S1600536813012592 ]

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