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

Akkurt, M.; Marzouk, A.A.; Abbasov, V.M.; Abdelhamid, A.A.; Gurbanov, A.V.

doi:10.1107/S1600536812041979

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 (C-C) = 0.003 Å
Disorder in main residue
R = 0.058
wR = 0.181
Data-to-parameter ratio = 18.8
Details

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

Mehmet Akkurt,^a ^* Adel A. Marzouk,^b Vagif. M. Abbasov,^c Antar A. Abdelhamid ^d and Atash V. Gurbanov ^d

^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). For biological properties of imidazoles, see: Puratchikody & Doble (2007); Bhatnagar et al. (2011); Antolini et al. (1999); Wang et al. (2002). For standard bond-length data, see: Allen et al. (1987).

Experimental

Crystal data

C₂₅H₂₂N₂O
M_r = 366.45
Monoclinic, P 2₁ /n
a = 18.3169 (7) Å
b = 9.6142 (3) Å
c = 23.1656 (8) Å
= 99.0261 (7)°
V = 4029.0 (2) Å³
Z = 8
Mo K radiation
= 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) T_min = 0.978, T_max = 0.985
44087 measured reflections
9608 independent reflections
6879 reflections with I > 2(I)
R_int = 0.026

Refinement

R[F² > 2(F²)] = 0.058
wR(F²) = 0.181
S = 1.01
9608 reflections
511 parameters
37 restraints
H-atom parameters constrained
_max = 0.60 e Å^-3
_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-HA	D-H	HA	DA	D-HA
C8-H8Cg5ⁱ	0.93	2.87	3.585 (2)	135
C28-H28ACg2ⁱⁱ	0.97	2.99	3.655 (6)	127
C33-H33Cg1ⁱⁱⁱ	0.93	2.86	3.592 (2)	137
C37-H37Cg1ⁱⁱ	0.93	2.96	3.789 (2)	150
C41-H41Cg3^iv	0.93	2.90	3.772 (10)	157
C41'-H41'Cg3^iv	0.93	2.85	3.705 (12)	154
C46-H46Cg4	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); cell refinement: SAINT-Plus (Bruker, 2001); data reduction: SAINT-Plus; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 for Windows (Farrugia, 2012); software used to prepare material for publication: WinGX (Farrugia, 2012) and PLATON (Spek, 2009).

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.
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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.
Mohamed, S. K., Akkurt, M., Fronczek, F. R., Marzouk, A. A. E. & Abdelhamid, A. A. (2012). Acta Cryst. E68, o2979-o2980.
Puratchikody, A. & Doble, M. (2007). Bioorg. Med. Chem. Lett. 15, 1083-1090.
Sheldrick, G. M. (2003). SADABS. University of Göttingen, Germany.
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.
Spek, A. L. (2009). Acta Cryst. D65, 148-155.
Wang, L., Woods, K. W. & Li, Q. (2002). J. Med. Chem. 45, 1697-1711.

organic compounds