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Volume 69 
Part 4 
Pages o474-o475  
April 2013  

Received 7 February 2013
Accepted 13 February 2013
Online 2 March 2013

Key indicators
Single-crystal X-ray study
T = 296 K
Mean [sigma](C-C) = 0.002 Å
Disorder in main residue
R = 0.043
wR = 0.110
Data-to-parameter ratio = 14.2
Details
Open access

2-[2-(4-Methoxyphenyl)-4,5-diphenyl-1H-imidazol-1-yl]ethanol

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,eMamedaliev Institute of Petrochemical Processes, National Academy of Sciences of Azerbaijan, Baku, Azerbaijan, and fDepartment of Organic Chemistry, Baku State University, Baku, Azerbaijan
Correspondence e-mail: shaabankamel@yahoo.com, akkurt@erciyes.edu.tr

In the title compound, C24H22N2O2, the central imidazole ring makes dihedral angles of 49.45 (8), 88.94 (9) and 19.43 (8)° with the benzene ring and the two phenyl rings, respectively. The dihedral angle between the phenyl rings is 77.86 (9)°, and they form dihedral angles of 49.06 (9) and 67.31 (8)° with the benzene ring. In the crystal, molecules are linked by O-H...N hydrogen bonds, forming chains along the b axis. These chains are connected by C-H...O hydrogen bonds, forming a two-dimensional network parallel to (100). In addition, C-H...[pi] interactions are also observed. The terminal C and O atoms of the ethanol group are disordered over two sets of sites with an occupancy ratio of 0.801 (5):0.199 (5).

Related literature

For imidazole derivatives as anticancer agents, see, for example: Krezel (1998[Krezel, I. (1998). Il Farmaco, 53, 342-345.]); Andreani et al. (2000[Andreani, A., Leoni, A., Locatelli, A., Morigi, R., Rambaldi, M., Recanatini, M. & Garaliene, V. (2000). Bioorg. Med. Chem. 8, 2359-2366.]). For related structures, see: Akkurt et al. (2012[Akkurt, M., Marzouk, A. A., Abbasov, V. M., Abdelhamid, A. A. & Gurbanov, A. V. (2012). Acta Cryst. E68, o3113-o3114.]); Mohamed et al. (2012[Mohamed, S. K., Akkurt, M., Fronczek, F. R., Marzouk, A. A. E. & Abdelhamid, A. A. (2012). Acta Cryst. E68, o2979-o2980.]). For further biological applications of imidazoles, see: Maier et al. (1989a[Maier, T., Schmierer, R., Bauer, K., Bieringer, H., Buerstell, H. & Sachse, B. (1989a). US Patent 4 820 335.],b[Maier, T., Schmierer, R., Bauer, K., Bieringer, H., Buerstell, H. & Sachse, B. (1989b). Chem. Abstr. 111, 19494.]). For standard bond-length data, see: Allen et al. (1987[Allen, F. H., Kennard, O., Watson, D. G., Brammer, L., Orpen, A. G. & Taylor, R. (1987). J. Chem. Soc. Perkin Trans. 2, pp. S1-19.]).

[Scheme 1]

Experimental

Crystal data
  • C24H22N2O2

  • Mr = 370.44

  • Monoclinic, P 21 /c

  • a = 14.3570 (4) Å

  • b = 13.2820 (4) Å

  • c = 10.7380 (3) Å

  • [beta] = 108.212 (1)°

  • V = 1945.05 (10) Å3

  • Z = 4

  • Mo K[alpha] radiation

  • [mu] = 0.08 mm-1

  • T = 296 K

  • 0.30 × 0.30 × 0.30 mm

Data collection
  • Bruker APEXII CCD diffractometer

  • Absorption correction: multi-scan (SADABS; Sheldrick, 1996[Sheldrick, G. M. (1996). SADABS. University of Göttingen, Germany.]) Tmin = 0.976, Tmax = 0.976

  • 18622 measured reflections

  • 3822 independent reflections

  • 3046 reflections with I > 2[sigma](I)

  • Rint = 0.022

Refinement
  • R[F2 > 2[sigma](F2)] = 0.043

  • wR(F2) = 0.110

  • S = 1.04

  • 3822 reflections

  • 269 parameters

  • 2 restraints

  • H-atom parameters constrained

  • [Delta][rho]max = 0.16 e Å-3

  • [Delta][rho]min = -0.18 e Å-3

Table 1
Hydrogen-bond geometry (Å, °)

Cg1 is the centroid of the C4-C9 benzene ring.

D-H...A D-H H...A D...A D-H...A
O1A-H1OA...N2i 0.82 2.01 2.829 (3) 175
C9-H9...O1Aii 0.93 2.58 3.452 (3) 156
C24-H24...O1Aiii 0.93 2.53 3.448 (4) 170
C23-H23...Cg1iii 0.93 2.90 3.736 (2) 151
Symmetry codes: (i) [-x+1, y+{\script{1\over 2}}, -z+{\script{1\over 2}}]; (ii) [x, -y+{\script{1\over 2}}, z-{\script{1\over 2}}]; (iii) [-x+1, y-{\script{1\over 2}}, -z+{\script{1\over 2}}].

Data collection: APEX2 (Bruker, 2005[Bruker (2005). APEX2. Bruker AXS Inc., Madison, Wisconsin, USA.]); cell refinement: SAINT-Plus (Bruker, 2001[Bruker (2001). SAINT-Plus. Bruker AXS Inc., Madison, Wisconsin, USA.]); data reduction: SAINT-Plus; 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: SU2561 ).


Acknowledgements

The authors are thankful to the National Academy of Sciences of Azerbaijan in collaboration with the Ministry of Higher Education of Egypt for funding this project. Manchester Metropolitan University, Erciyes University and Baku State University are gratefully acknowledged for supporting the study.

References

Akkurt, M., Marzouk, A. A., Abbasov, V. M., Abdelhamid, A. A. & Gurbanov, A. V. (2012). Acta Cryst. E68, o3113-o3114.  [CSD] [CrossRef] [details]
Allen, F. H., Kennard, O., Watson, D. G., Brammer, L., Orpen, A. G. & Taylor, R. (1987). J. Chem. Soc. Perkin Trans. 2, pp. S1-19.
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.  [ISI] [CrossRef] [ChemPort] [details]
Andreani, A., Leoni, A., Locatelli, A., Morigi, R., Rambaldi, M., Recanatini, M. & Garaliene, V. (2000). Bioorg. Med. Chem. 8, 2359-2366.  [CrossRef] [PubMed] [ChemPort]
Bruker (2001). SAINT-Plus. Bruker AXS Inc., Madison, Wisconsin, USA.
Bruker (2005). APEX2. Bruker AXS Inc., Madison, Wisconsin, USA.
Farrugia, L. J. (2012). J. Appl. Cryst. 45, 849-854.  [ISI] [CrossRef] [ChemPort] [details]
Krezel, I. (1998). Il Farmaco, 53, 342-345.  [ChemPort] [PubMed]
Maier, T., Schmierer, R., Bauer, K., Bieringer, H., Buerstell, H. & Sachse, B. (1989a). US Patent 4 820 335.
Maier, T., Schmierer, R., Bauer, K., Bieringer, H., Buerstell, H. & Sachse, B. (1989b). Chem. Abstr. 111, 19494.
Mohamed, S. K., Akkurt, M., Fronczek, F. R., Marzouk, A. A. E. & Abdelhamid, A. A. (2012). Acta Cryst. E68, o2979-o2980.  [CSD] [CrossRef] [details]
Sheldrick, G. M. (1996). SADABS. University of Göttingen, Germany.
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.  [CrossRef] [details]
Spek, A. L. (2009). Acta Cryst. D65, 148-155.  [ISI] [CrossRef] [details]


Acta Cryst (2013). E69, o474-o475   [ doi:10.1107/S1600536813004285 ]

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