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

Mehmet Akkurt; Adel A Marzouk; Vagif M Abbasov; Antar A Abdelhamid; Atash V Gurbanov

doi:10.1107/S1600536812041979

. 2012 Oct 13;68(Pt 11):o3113–o3114. doi: 10.1107/S1600536812041979

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, Atash V Gurbanov ^d

PMCID: PMC3515219 PMID: 23284439

Abstract

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⋯π 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,
a = 18.3169 (7) Å
b = 9.6142 (3) Å
c = 23.1656 (8) Å
β = 99.0261 (7)°
V = 4029.0 (2) Å³
Z = 8
Mo Kα radiation
μ = 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 > 2σ(I)
R _int = 0.026

Refinement

R[F ² > 2σ(F ²)] = 0.058
wR(F ²) = 0.181
S = 1.01
9608 reflections
511 parameters
37 restraints
H-atom parameters constrained
Δρ_max = 0.60 e Å⁻³
Δρ_min = −0.39 e Å⁻³

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 Material

Click here for additional data file.^{(49.5KB, cif)}

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S1600536812041979/su2509sup1.cif

e-68-o3113-sup1.cif^{(49.5KB, cif)}

Click here for additional data file.^{(469.9KB, hkl)}

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536812041979/su2509Isup2.hkl

e-68-o3113-Isup2.hkl^{(469.9KB, hkl)}

Click here for additional data file.^{(7.5KB, cml)}

Supplementary material file. DOI: 10.1107/S1600536812041979/su2509Isup3.cml

Additional supplementary materials: crystallographic information; 3D view; checkCIF report

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⋯Cg3^iv	0.93	2.90	3.772 (10)	157
C41′—H41′⋯Cg3^iv	0.93	2.85	3.705 (12)	154
C46—H46⋯Cg4	0.93	3.00	3.712 (2)	135

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Symmetry codes: (i) Inline graphic ; (ii) ; (iii) ; (iv) .

Acknowledgments

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

supplementary crystallographic information

Comment

Imidazole derivatives are a great class of heterocyclic compounds due to their wide range of pharmacological and biological activities They exhibited as inhibitors of p38 MAP kinase, fungicides, herbicides, plant growth regulators, antibacterial, antitumour, pesticides and therapeutic agents (Bhatnagar et al. (2011); Puratchikody & Doble 2007; Wang et al., 2002 and Antolini, et al., 1999). They also serve as useful building blocks for synthesis of diverse class of bioactive molecules. Further to our study on synthesis of bioactive heterocyclic molecules we herein report the crystal structure of the title compound.

The molecular structure of the two independent molecules (A and B) of the title compound are illustrated in Fig. 1 Both molecules have a similar conformation. The –N—C(H₂)—C(H)—C(H₂) torsion angles of the prop-1-ene group are 0.5 (3) and 1.3 (4)° in molecules A and B, respectively. The bond lengths and angles of both molecules are comparable and similar to the values reported in the literature (Allen et al., 1987).

In molecule A, the central imidazole ring (N1/N2/C4–C6) forms dihedral angles of 88.26 (10), 12.74 (11) and 22.06 (9)° with the C7–C12 and C13–C18 phenyl and C19—C24 benzene rings, respectively. The corresponding angles in molecule B are 79.24 (10), 3.5 (5) [22.6 (5)] and 67.49 (10)°, with the C32–C37 and disordered C38–C43 [C38'–C43'] phenyl and C44—C49 benzene rings, respectively. In the disordered phenyl group of molecule B, the dihedral angle between the two parts is 19.1 (7)°.

In the crystal, there is no classical hydrogen bonds; the molecules are linked via C—H···π interactions (Table 1 and Fig. 2).

Experimental

The title compound was prepared, among series of imidazole derivatives, according to our reported method (Mohamed et al., 2012) in 88% yield. Suitable single crystals were obtained by slow evaporation of a solution in ethanol M.p. 385–387 K.