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Volume 69 
Part 7 
Pages o1105-o1106  
July 2013  

Received 10 June 2013
Accepted 11 June 2013
Online 15 June 2013

Key indicators
Single-crystal X-ray study
T = 100 K
Mean [sigma](C-C) = 0.003 Å
Disorder in main residue
R = 0.058
wR = 0.149
Data-to-parameter ratio = 17.6
Details
Open access

Prop-2-en-1-yl 4-(4,5-diphenyl-1H-imidazol-2-yl)benzoate

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,eChemistry Department, Faculty of Science, Sohag University, 82524 Sohag, Egypt, and fDepartment of Organic Chemistry, Faculty of Science, Institute of Biotechnology, Granada University, Granada, E-18071, Spain
Correspondence e-mail: shaabankamel@yahoo.com

The title compound, C25H20N2O2, crystallized with two molecules in the asymmetric unit, in one of which the atoms of the terminal propenyl group are disordered over two sets of sites, with a refined occupancy ratio of 0.870 (4):0.130 (4). The central imidazole ring makes dihedral angles of 25.51 (11), 40.73 (11) and 27.36 (11)° with the three pendant rings in one molecule and 22.56 (10), 60.72 (10) and 5.85 (10)° in the other. In the crystal, molecules are linked by N-H...N and C-H...O hydrogen bonds, forming a three-dimensional network. The crystal structure also features C-H...[pi] interactions and [pi]-[pi] stacking [centroid-centroid distances = 3.8834 (18) and 3.9621 (17) Å] interactions.

Related literature

For the synthesis and biological activity of imidazole compounds, see, for example: Bhatnagar et al. (2011[Bhatnagar, A., Sharma, P. K. & Kumar, N. (2011). Int. J. PharmTech Res. 3, 268-282.]); Sisko & Mellinger (2002[Sisko, J. & Mellinger, M. (2002). Pure Appl. Chem. 74, 1349-1357.]). 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.]).

[Scheme 1]

Experimental

Crystal data
  • C25H20N2O2

  • Mr = 380.43

  • Monoclinic, P 21 /c

  • a = 15.705 (5) Å

  • b = 14.888 (5) Å

  • c = 17.589 (6) Å

  • [beta] = 105.151 (4)°

  • V = 3970 (2) Å3

  • Z = 8

  • Mo K[alpha] radiation

  • [mu] = 0.08 mm-1

  • T = 100 K

  • 0.73 × 0.35 × 0.15 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 = 0.967, Tmax = 0.988

  • 46196 measured reflections

  • 9345 independent reflections

  • 6507 reflections with I > 2[sigma](I)

  • Rint = 0.064

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

  • wR(F2) = 0.149

  • S = 1.02

  • 9345 reflections

  • 530 parameters

  • 42 restraints

  • H-atom parameters constrained

  • [Delta][rho]max = 0.51 e Å-3

  • [Delta][rho]min = -0.47 e Å-3

Table 1
Hydrogen-bond geometry (Å, °)

Cg1, Cg2 and Cg3 are the centroids of the N1/N2/C1-C3 1H-imidazole ring and the C4-C9 and C10-C15 phenyl rings, respectively.

D-H...A D-H H...A D...A D-H...A
N1-H1N...N4i 0.90 (2) 2.14 (2) 3.037 (2) 176 (2)
N3-H3N...N2 0.89 (2) 2.06 (2) 2.925 (2) 164 (2)
C7-H7...O1ii 0.95 2.45 3.254 (3) 142
C32-H32...O3iii 0.95 2.51 3.439 (3) 167
C23-H23A...Cg1iv 0.99 2.74 3.524 (3) 136
C25A-H25B...Cg2v 0.95 2.79 3.687 (3) 158
C37-H37...Cg3vi 0.95 2.90 3.634 (3) 134
C25B-H25D...Cg2v 0.95 2.68 3.44 (2) 137
Symmetry codes: (i) [x, -y+{\script{1\over 2}}, z-{\script{1\over 2}}]; (ii) x, y-1, z; (iii) x-1, y, z; (iv) [-x+1, y+{\script{1\over 2}}, -z+{\script{3\over 2}}]; (v) [x, -y+{\script{1\over 2}}, z+{\script{1\over 2}}]; (vi) -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: SIR97 (Altomare et al., 1999[Altomare, A., Burla, M. C., Camalli, M., Cascarano, G. L., Giacovazzo, C., Guagliardi, A., Moliterni, A. G. G., Polidori, G. & Spagna, R. (1999). J. Appl. Cryst. 32, 115-119.]); 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: HG5323 ).


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]
Altomare, A., Burla, M. C., Camalli, M., Cascarano, G. L., Giacovazzo, C., Guagliardi, A., Moliterni, A. G. G., Polidori, G. & Spagna, R. (1999). J. Appl. Cryst. 32, 115-119.  [Web of Science] [CrossRef] [ChemPort] [IUCr Journals]
Bhatnagar, A., Sharma, P. K. & Kumar, N. (2011). Int. J. PharmTech Res. 3, 268-282.  [ChemPort]
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]
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]
Sheldrick, G. M. (2004). SADABS. University of Göttingen, Germany.
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.  [CrossRef] [ChemPort] [IUCr Journals]
Sisko, J. & Mellinger, M. (2002). Pure Appl. Chem. 74, 1349-1357.  [Web of Science] [CrossRef] [ChemPort]
Spek, A. L. (2009). Acta Cryst. D65, 148-155.  [Web of Science] [CrossRef] [ChemPort] [IUCr Journals]


Acta Cryst (2013). E69, o1105-o1106   [ doi:10.1107/S160053681301619X ]

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