2-(4-Bromo­phen­yl)-1-pentyl-4,5-diphenyl-1H-imidazole

Shaaban K Mohamed; Mehmet Akkurt; Kuldip Singh; Adel A Marzouk; Mustafa R Albayati

doi:10.1107/S1600536813021983

. 2013 Aug 14;69(Pt 9):o1417. doi: 10.1107/S1600536813021983

2-(4-Bromophenyl)-1-pentyl-4,5-diphenyl-1H-imidazole

Shaaban K Mohamed ^a,^b, Mehmet Akkurt ^c, Kuldip Singh ^d, Adel A Marzouk ^e, Mustafa R Albayati ^f,^*

PMCID: PMC3884403 PMID: 24427052

Abstract

The title compound, C₂₆H₂₅BrN₂, is isomorphous with the chloro derivative [2-(4-chlorophenyl)-1-pentyl-4,5-diphenyl-1H-imidazole; Mohamed et al. (2013 ▶). Acta Cryst. E69, o846–o847]. The two phenyl rings and the 4-bromophenyl ring are oriented at dihedral angles of 30.1 (2), 64.3 (3) and 42.0 (2)°, respectively, with respect to the imidazole ring. In the crystal, molecules stack in columns along the b-axis direction, however, there are no significant intermolecular interactions present.

Related literature

For biological and synthetic applications of imidazole derivatives, see: Maier et al. (1989a ▶,b ▶); Welton (1999 ▶); Hermann & Kocher (1997 ▶). For related structures, see: Akkurt et al. (2013 ▶); Mohamed et al. (2013 ▶); Simpson et al. (2013 ▶).

Experimental

Crystal data

C₂₆H₂₅BrN₂
M _r = 445.39
Monoclinic,
a = 10.665 (5) Å
b = 9.619 (5) Å
c = 21.541 (10) Å
β = 91.092 (9)°
V = 2209.4 (19) Å³
Z = 4
Mo Kα radiation
μ = 1.88 mm⁻¹
T = 150 K
0.36 × 0.16 × 0.03 mm

Data collection

Bruker APEXII CCD area-detector diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2011 ▶) T _min = 0.600, T _max = 0.969
16966 measured reflections
4329 independent reflections
2328 reflections with I > 2σ(I)
R _int = 0.187

Refinement

R[F ² > 2σ(F ²)] = 0.066
wR(F ²) = 0.116
S = 0.88
4329 reflections
263 parameters
H-atom parameters constrained
Δρ_max = 0.61 e Å⁻³
Δρ_min = −1.05 e Å⁻³

Data collection: APEX2 (Bruker, 2011 ▶); cell refinement: SAINT (Bruker, 2011 ▶); data reduction: SAINT; 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

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S1600536813021983/su2633sup1.cif

e-69-o1417-sup1.cif^{(28.1KB, cif)}

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536813021983/su2633Isup2.hkl

e-69-o1417-Isup2.hkl^{(212.1KB, hkl)}

Click here for additional data file.^{(7.9KB, cml)}

Supplementary material file. DOI: 10.1107/S1600536813021983/su2633Isup3.cml

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

Acknowledgments

Manchester Metropolitan University, Erciyes University and the University of Leicester are gratefully acknowledged for supporting this study.

supplementary crystallographic information

1. Comment

Many substituted imidazoles exhibit diverse pharmaceutical properties and are known inhibitors of fungicides and herbicides, plant growth regulators and therapeutic agents (Maier et al., 1989a,b). Moreover, they are of interest for environmental and green chemistry applications, and have been prepared and used as a large class of ionic liquids and Lewis base catalysts (Welton, 1999; Hermann & Kocher, 1997). As part of our ongoing study of the synthesis (Akkurt et al., 2013; Mohamed et al., 2013; Simpson et al., 2013) and biological applications of tetrasubstituted imidazoles, we herein report on the synthesize and crystal structure of the title compound.

The title compound, Fig. 1, and the chloro derivative, 2-(4-Chlorophenyl)-1-pentyl-4,5-diphenyl-1H-imidazole, whose crystal structure has been reported by (Mohamed et al., 2013), are isomorphous. In the title compound the phenyl rings (C10–C15 and C16–C21) and the 4-bromophenyl ring (C4–C9) make dihedral angles of 30.1 (2), 64.3 (3) and 42.0 (2)°, respectively, with the imidazole ring (N1/N2/C1–C3). The values of the bond lengths and bond angles fall within the normal range and are comparable with those reported for similar structures (Akkurt et al., 2013; Mohamed et al., 2013; Simpson et al., 2013).

In the crystal, the molecules stack in columns along the b axis direction however, there are no significant intermolecular interactions present (Fig. 2).

2. Experimental

The title compound was synthesized following our previously reported procedure (Mohamed et al., 2013). Colourless plates of the title compound (M.p. 396–398 K) were collected with 84% yield. Crystals of sufficient quality for the X-ray diffraction study were obtained by slow evaporation of an ethanol solution of the title compound.