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

Shaaban K Mohamed; Mehmet Akkurt; Kuldip Singh; Adel A Marzouk; Antar A Abdelhamid

doi:10.1107/S1600536813018229

. 2013 Jul 13;69(Pt 8):o1243. doi: 10.1107/S1600536813018229

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

Shaaban K Mohamed ^a,^b,^*, Mehmet Akkurt ^c, Kuldip Singh ^d, Adel A Marzouk ^e, Antar A Abdelhamid ^f

PMCID: PMC3793746 PMID: 24109333

Abstract

In the title compound, C₂₆H₂₅ClN₂, the phenyl rings and the 2-(4-chlorophenyl) group make dihedral angles of 30.03 (11), 67.49 (12) and 41.56 (11)°, respectively, with the imidazole ring. In the crystal, the molecules interact with each other via very weak C—H⋯π contacts, forming layers parallel to (110).

Related literature

For biological applications of imidazole derivatives, see: Shalini et al. (2011 ▶); Ramesh et al. (2012 ▶); Wolkenberg et al. (2004 ▶). For related structures, see: Simpson et al. (2013 ▶); Akkurt et al. (2013 ▶). graphic file with name e-69-o1243-scheme1.jpg

Experimental

Crystal data

C₂₆H₂₅ClN₂
M _r = 400.93
Monoclinic,
a = 10.471 (2) Å
b = 9.7798 (19) Å
c = 21.682 (4) Å
β = 91.080 (4)°
V = 2219.9 (7) Å³
Z = 4
Mo Kα radiation
μ = 0.19 mm⁻¹
T = 150 K
0.36 × 0.14 × 0.11 mm

Data collection

Bruker APEX 2000 CCD area-detector diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2001 ▶) T _min = 0.969, T _max = 0.980
16940 measured reflections
4346 independent reflections
2593 reflections with I > 2σ(I)
R _int = 0.088

Refinement

R[F ² > 2σ(F ²)] = 0.053
wR(F ²) = 0.110
S = 0.89
4346 reflections
263 parameters
H-atom parameters constrained
Δρ_max = 0.26 e Å⁻³
Δρ_min = −0.31 e Å⁻³

Data collection: SMART (Bruker, 2001 ▶); cell refinement: SAINT (Bruker, 2001 ▶); 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/S1600536813018229/yk2095sup1.cif

e-69-o1243-sup1.cif^{(29.8KB, cif)}

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536813018229/yk2095Isup2.hkl

e-69-o1243-Isup2.hkl^{(238.4KB, hkl)}

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

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

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C20—H20⋯C25ⁱ	0.95	3.00	3.887 (3)	157
C24—H24⋯C13ⁱⁱ	0.95	2.78	3.697 (3)	163
C28—H28⋯N3ⁱⁱⁱ	0.95	2.88	3.444 (3)	119
C28—H28⋯C17ⁱⁱⁱ	0.95	3.00	3.894 (3)	158

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

Acknowledgments

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

supplementary crystallographic information

Comment

Various substituted imidazole derivatives have been found to possess a significant biological exhibition such as anti-helminthic, analgesic, antibacterial, antifungal, antiviral, tuberculostatic, cytostatic, and anti-inflammation activities (Shalini et al., 2011). Tetra-substituted imidazoles in particular represent the core structure in many biological systems such as Losartan, Trifenagrel, Eprosartan and Olmesartan (Ramesh et al., 2012; Wolkenberg et al., 2004). Based on literature and further to our ongoing study in synthesis of bio-active molecules the title compound has been synthesized and herein we report its crystal structure.

As shown in Fig. 1, the title molecule adopts a non-planar conformation. The two phenyl (C17–C22 and C23–C28) and 2-(4-chlorophenyl) (C11–C16) groups make the dihedral angles of 30.03 (11), 67.49 (12) and 41.56 (11) °, respectively, with the imidazole ring (N1/C2/N3/C4/C5). The N1–C6–C7–C8 and C7–C8–C9–C10 torsion angles are -168.61 (16) and -176.82 (19)°, respectively. The values of the geometric parameters of (I) are in the normal range and comparable to those reported for the similar compounds (Simpson et al., 2013; Akkurt et al., 2013).

The crystal structure of (I) is stabilized by intra and intermolecular Cl···H(C) contacts [Cl1···H13 = 2.80 Å, Cl1···H15 = 2.80 Å, Cl1···H6Aⁱ = 3.10 Å, Cl1···H8Bⁱ = 3.05 Å, Cl1···H24ⁱⁱ = 3.14 Å, Cl1···H10Bⁱⁱⁱ = 3.02 Å (symmetry codes: (i) 1 - x, 1 - y, 2 - z; (ii) 2 - x, 1 - y, 2 - z; (iii) -1/2 + x, 3/2 - y, 1/2 + z)]. Fig. 2 shows the molecular packing of (I) along the b axis.

Experimental

The title compound was synthesized following the previously reported procedure (Simpson et al., 2013). Colourless grains of product (M.p. 399 K) were collected with 89% yield. The crystals of sufficient quality for X-ray diffraction study were obtained by slow evaporation of the ethanol solution of the title compound.