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Volume 68 
Part 11 
Pages o3113-o3114  
November 2012  

Received 5 October 2012
Accepted 7 October 2012
Online 13 October 2012

Key indicators
Single-crystal X-ray study
T = 296 K
Mean [sigma](C-C) = 0.003 Å
Disorder in main residue
R = 0.058
wR = 0.181
Data-to-parameter ratio = 18.8
Details
Open access

2-(4-Methoxyphenyl)-4,5-diphenyl-1-(prop-2-en-1-yl)-1H-imidazole

aDepartment of Physics, Faculty of Sciences, Erciyes University, 38039 Kayseri, Turkey,bPharmaceutical Chemistry Department, Faculty of Pharmacy, Al Azhar University, Egypt,cMamedaliev Institute of Petrochemical Processes, National Academy of Sciences of Azerbaijan, Baku, Azerbaijan, and dDepartment of Organic Chemistry, Baku State University, Baku, Azerbaijan
Correspondence e-mail: akkurt@erciyes.edu.tr

The asymmetric unit of the title compound, C25H22N2O, contains two independent molecules (A and B), with significantly different conformations. In molecule A, the central imidazole ring makes dihedral angles of 88.26 (10) and 12.74 (11)° with the two phenyl rings, and 22.06 (9)° with the benzene ring. In molecule B, one of the phenyl rings is disordered over two sites, each having an occupancy of 0.5. Here the central imidazole ring forms dihedral angles of 79.24 (10)° with the ordered phenyl ring, and 3.5 (5) and 22.6 (5)° with the two parts of the disordered phenyl ring. The dihedral angle involving the benzene ring is 67.49 (10)°. The -N-C(H2)-C(H)-C(H2) torsion angles of the prop-1-ene group in the two molecules are very similar, 0.5 (3) and 1.3 (4)° for molecules A and B, respectively. The crystal structure is stabilized by C-H...[pi] interactions.

Related literature

For the synthesis, see: 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 biological properties of imidazoles, see: Puratchikody & Doble (2007[Puratchikody, A. & Doble, M. (2007). Bioorg. Med. Chem. Lett. 15, 1083-1090.]); Bhatnagar et al. (2011[Bhatnagar, A., Sharma, P. K. & Kumar, N. (2011). Int. J. Pharm. Tech. Res. 3, 268-282.]); Antolini et al. (1999[Antolini, M., Bozzoli, A. & Ghiron, C. (1999). Bioorg. Med. Chem. Lett. 9, 1023-1028.]); Wang et al. (2002[Wang, L., Woods, K. W. & Li, Q. (2002). J. Med. Chem. 45, 1697-1711.]). 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
  • C25H22N2O

  • Mr = 366.45

  • Monoclinic, P 21 /n

  • a = 18.3169 (7) Å

  • b = 9.6142 (3) Å

  • c = 23.1656 (8) Å

  • [beta] = 99.0261 (7)°

  • V = 4029.0 (2) Å3

  • Z = 8

  • Mo K[alpha] radiation

  • [mu] = 0.07 mm-1

  • T = 296 K

  • 0.30 × 0.30 × 0.20 mm

Data collection
  • Bruker APEXII CCD diffractometer

  • Absorption correction: multi-scan (SADABS; Sheldrick, 2003[Sheldrick, G. M. (2003). SADABS. University of Göttingen, Germany.]) Tmin = 0.978, Tmax = 0.985

  • 44087 measured reflections

  • 9608 independent reflections

  • 6879 reflections with I > 2[sigma](I)

  • Rint = 0.026

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

  • wR(F2) = 0.181

  • S = 1.01

  • 9608 reflections

  • 511 parameters

  • 37 restraints

  • H-atom parameters constrained

  • [Delta][rho]max = 0.60 e Å-3

  • [Delta][rho]min = -0.39 e Å-3

Table 1
Hydrogen-bond geometry (Å, °)

Cg1, Cg2, Cg3, Cg4 and Cg5 are the centroids of the N3/N4/C29-C31, C38'-C43', C7-C12, C13-C18 and C19-C24 rings, respectively.

D-H...A D-H H...A D...A D-H...A
C8-H8...Cg5i 0.93 2.87 3.585 (2) 135
C28-H28A...Cg2ii 0.97 2.99 3.655 (6) 127
C33-H33...Cg1iii 0.93 2.86 3.592 (2) 137
C37-H37...Cg1ii 0.93 2.96 3.789 (2) 150
C41-H41...Cg3iv 0.93 2.90 3.772 (10) 157
C41'-H41'...Cg3iv 0.93 2.85 3.705 (12) 154
C46-H46...Cg4 0.93 3.00 3.712 (2) 135
Symmetry codes: (i) [-x+{\script{1\over 2}}, y+{\script{1\over 2}}, -z+{\script{1\over 2}}]; (ii) [-x+{\script{3\over 2}}, y-{\script{1\over 2}}, -z+{\script{1\over 2}}]; (iii) [-x+{\script{3\over 2}}, y+{\script{1\over 2}}, -z+{\script{1\over 2}}]; (iv) x+1, y, z.

Data collection: APEX2 (Bruker, 2005[Bruker (2005). APEX2. Bruker AXS, Madison, Wisconsin, USA.]); cell refinement: SAINT-Plus (Bruker, 2001[Bruker (2001). SAINT-Plus. Bruker AXS, Madison, Wisconsin, USA.]); data reduction: SAINT-Plus; 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: SU2509 ).


Acknowledgements

The National Academy of Sciences of Azerbaijan, Erciyes University and Baku state University are gratefully acknowledged for supporting this study.

References

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.
Antolini, M., Bozzoli, A. & Ghiron, C. (1999). Bioorg. Med. Chem. Lett. 9, 1023-1028.  [CrossRef] [PubMed] [ChemPort]
Bhatnagar, A., Sharma, P. K. & Kumar, N. (2011). Int. J. Pharm. Tech. Res. 3, 268-282.  [ChemPort]
Bruker (2001). SAINT-Plus. Bruker AXS, Madison, Wisconsin, USA.
Bruker (2005). APEX2. Bruker AXS, Madison, Wisconsin, USA.
Farrugia, L. J. (2012). J. Appl. Cryst. 45, 849-854.  [ISI] [CrossRef] [ChemPort] [details]
Mohamed, S. K., Akkurt, M., Fronczek, F. R., Marzouk, A. A. E. & Abdelhamid, A. A. (2012). Acta Cryst. E68, o2979-o2980.  [CrossRef] [details]
Puratchikody, A. & Doble, M. (2007). Bioorg. Med. Chem. Lett. 15, 1083-1090.  [ChemPort]
Sheldrick, G. M. (2003). 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]
Wang, L., Woods, K. W. & Li, Q. (2002). J. Med. Chem. 45, 1697-1711.  [ISI] [CrossRef] [PubMed] [ChemPort]


Acta Cryst (2012). E68, o3113-o3114   [ doi:10.1107/S1600536812041979 ]

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