2-(3,4-Dimeth­oxy­phen­yl)-4,5-diphenyl-1-(prop-2-en-1-yl)-1H-imidazole

Shaaban K Mohamed; Mehmet Akkurt; Frank R Fronczek; Adel A E Marzouk; Antar A Abdelhamid

doi:10.1107/S1600536812039566

. 2012 Sep 22;68(Pt 10):o2979–o2980. doi: 10.1107/S1600536812039566

2-(3,4-Dimethoxyphenyl)-4,5-diphenyl-1-(prop-2-en-1-yl)-1H-imidazole

Shaaban K Mohamed ^a, Mehmet Akkurt ^b,^*, Frank R Fronczek ^c, Adel A E Marzouk ^d, Antar A Abdelhamid ^a

PMCID: PMC3470344 PMID: 23125757

Abstract

In the title compound, C₂₆H₂₄N₂O₂, the planar 1H-imidazole ring makes dihedral angles of 35.78 (4), 26.35 (5) and 69.75 (5)°, respectively, with the dimethoxyphenyl ring and the phenyl rings in the 4- and 5-positions. In the crystal, C—H⋯O hydrogen bonds connect neighbouring molecules, forming infinite chains running along the b axis. Furthermore, the crystal structure exhibits a C—H-⋯π interaction between a methyl H atom and a phenyl ring from an adjacent molecule.

Related literature

For the synthesis of imidazole compounds, see: Shalini et al. (2010 ▶). For the medicinal properties of imidazole derivatives, see: Adams et al. (2001 ▶); Nakamura et al. (2004 ▶); Venkatesan et al. (2008 ▶); Nanterment et al. (2004 ▶); Roman et al. (2007 ▶); Congiu et al. (2008 ▶). For standard bond distances, see: Allen et al. (1987 ▶).

Experimental

Crystal data

C₂₆H₂₄N₂O₂
M _r = 396.47
Triclinic,
a = 8.9683 (4) Å
b = 10.7916 (5) Å
c = 11.7219 (5) Å
α = 110.174 (2)°
β = 106.267 (2)°
γ = 91.991 (3)°
V = 1011.32 (8) Å³
Z = 2
Mo Kα radiation
μ = 0.08 mm⁻¹
T = 90 K
0.36 × 0.12 × 0.06 mm

Data collection

Bruker Kappa APEXII DUO diffractometer
Absorption correction: multi-scan (SADABS; Sheldrick, 2004 ▶) T _min = 0.971, T _max = 0.995
17346 measured reflections
6149 independent reflections
4408 reflections with I > 2σ(I)
R _int = 0.039
Standard reflections: 0

Refinement

R[F ² > 2σ(F ²)] = 0.048
wR(F ²) = 0.127
S = 1.02
6149 reflections
273 parameters
H-atom parameters constrained
Δρ_max = 0.46 e Å⁻³
Δρ_min = −0.25 e Å⁻³

Data collection: APEX2 (Bruker, 2005 ▶); cell refinement: SAINT (Bruker, 2005 ▶); data reduction: SAINT; program(s) used to solve structure: SIR97 (Altomare et al., 1999 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997 ▶) and PLATON (Spek, 2009 ▶); software used to prepare material for publication: WinGX (Farrugia, 1999 ▶) and PARST (Nardelli, 1983 ▶).

Supplementary Material

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S1600536812039566/bt6835sup1.cif

e-68-o2979-sup1.cif^{(29.8KB, cif)}

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536812039566/bt6835Isup2.hkl

e-68-o2979-Isup2.hkl^{(301KB, hkl)}

Supplementary material file. DOI: 10.1107/S1600536812039566/bt6835Isup3.cml

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

Table 1. Hydrogen-bond geometry (Å, °).

Cg3 is the centroid of the C15–C20 phenyl ring.

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C7—H9B⋯O1ⁱ	0.96	2.57	3.515 (2)	170
C8—H8B⋯Cg3ⁱⁱ	0.96	2.98	3.8316 (17)	149

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

Acknowledgments

Manchester Metropolitan University, Erciyes University and Louisiana State University are gratefully acknowledged for supporting this study.

supplementary crystallographic information

Comment

The high therapeutic properties of the imidazole related drugs have encouraged the medicinal chemists to synthesize a large number of novel chemotherapeutic agents incorporating the imidazole nucleus (Shalini et al., 2010). The broad medicinal properties of imidazole drugs include anticancer, β-lactamase inhibitors, 20-HETE (20-hydroxy-5,8,11,14-eicosatetraenoic acid) synthase inhibitors, carboxypeptidase inhibitors, hemeoxygenase inhibitors, anti-aging agents, anticoagulants, anti-inflammatory, antibacterial, antifungal, antiviral, anti-tubercular, anti-diabetic and antimalarial (Congiu et al., 2008; Venkatesan et al., 2008; Nakamura et al., 2004; Roman et al., 2007; Nanterment et al., 2004 and Adams et al., 2001). In this respect and in continuation of our on-going study for synthesis of bioactive molecules, we herein report synthesis and crystal structure of the title compound (I) among series of other imidazole derivatives.

The molecular structure of (I), (Fig. 1), has not a planar conformation. The (N1/N2/C9—C11) 1H-imidazole ring which is planar [maximum deviation = 0.005 (1) Å for C11] forms dihedral angles of 35.78 (4), 26.35 (5) and 69.75 (5)°, respectively, with the C1–C6 benzene ring and the C15–20 and C21–C26 phenyl rings. The plane of the allyl group makes a dihedral angle of 82.09 (12)° with the plane of the 1H-imidazole ring.

In (I), all bond lengths and bond angles are within normal range (Allen et al., 1987). The C3–C4–O1–C8 and C4–C3–O2–C7 torsion angles are 171.98 (13) and -176.30 (13)°, respectively.

In the crystal packing, molecules are linked by C—H···O hydrogen bonds, forming infinite chains running along the b axis (Table 1, Figs. 2 & 3). In addition, a C–H···π interaction is observed between the (C8)H8B methyl H atom and the C15–C20 phenyl ring of the adjacent molecule (Table 1).

Experimental

A mixture of 25 ml. of dimethyl sulfoxide and 2.4 g. (40 mmol) of potassium hydroxide was added in a 50-ml. volumetric flask equipped with a magnetic stirring bar. The mixture was stirred at room temperature for 5 minutes before adding of 3.26 g. (10 mmole) of 2-(3,4-dimethoxyphenyl)-4,5-diphenyl-1H-imidazole. Stirring was continued for 45 minutes, then 4.80 g. (20 mmol) of allylbromide was added. After being stirred for an additional 45 minutes the mixture was diluted with 20 ml. of water. The organic product was extracted with three 20-ml. portions of diethyl ether, and each ether layer was washed with three 10-ml. portions of water. The combined ether layers were dried over calcium chloride, and the solvent was removed at slightly reduced pressure. The excess allyl bromide was removed by distillation at approximately 15 mm. The residue was solidified upon cooling and scratching to furnish the title compound (3.22 g; 88%). Mono crystals suitable for X-ray analyses were obtained by slow evaporation method from ethanol at room temperature. M.p. 486 – 488 K.