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

Mehmet Akkurt; Shaaban K Mohamed; Adel A E Marzouk; V M Abbasov; Francisco Santoyo-Gonzalez

doi:10.1107/S1600536813014104

. 2013 May 31;69(Pt 6):o988–o989. doi: 10.1107/S1600536813014104

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

Mehmet Akkurt ^a, Shaaban K Mohamed ^b,^c,^*, Adel A E Marzouk ^d, V M Abbasov ^e, Francisco Santoyo-Gonzalez ^f

PMCID: PMC3685121 PMID: 23795140

Abstract

In the title compound, C₂₄H₂₀N₂, one of the ring C atoms and one of the ring N atoms are disordered over two sets of sites in a 0.615 (3):0.385 (3) ratio. The two parts of the disordered imidazole ring adopt an envelope conformation, with the undisordered ring N atom as the flap, displaced by −0.118 (6) and 0.226 (7) Å, respectively, in the two disorder components from the plane through the other ring atoms. The crystal structure features C—H⋯N hydrogen bonds and C—H⋯π interactions, which lead to the formation of infinite chains along [010].

Related literature

For the biological significance of imidazole derivatives, see, for example: Kumar (2010 ▶); Castaño et al. (2008 ▶); Banfi et al. (2006 ▶); Bogle et al. (1994 ▶). For the synthesis and the structures of similar imidazoles, see: Mohamed et al. (2013a ▶,b ▶); Akkurt et al. (2013 ▶). For puckering parameters, see: Cremer & Pople (1975 ▶).

Experimental

Crystal data

C₂₄H₂₀N₂
M _r = 336.42
Monoclinic,
a = 10.362 (3) Å
b = 8.938 (2) Å
c = 19.387 (5) Å
β = 90.340 (5)°
V = 1795.5 (8) Å³
Z = 4
Mo Kα radiation
μ = 0.07 mm⁻¹
T = 100 K
0.14 × 0.14 × 0.003 mm

Data collection

Bruker SMART APEX CCD area-detector diffractometer
Absorption correction: refined from ΔF (XABS2; Parkin et al., 1995 ▶) T _min = 0.990, T _max = 1.000
17127 measured reflections
3168 independent reflections
2442 reflections with I > 2σ(I)
R _int = 0.046

Refinement

R[F ² > 2σ(F ²)] = 0.062
wR(F ²) = 0.183
S = 1.04
3168 reflections
299 parameters
12 restraints
H-atom parameters constrained
Δρ_max = 0.49 e Å⁻³
Δρ_min = −0.29 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

Click here for additional data file.^{(34.1KB, cif)}

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S1600536813014104/zp2005sup1.cif

e-69-0o988-sup1.cif^{(34.1KB, cif)}

Click here for additional data file.^{(155.5KB, hkl)}

Structure factors: contains datablock(s) shelxl. DOI: 10.1107/S1600536813014104/zp2005Isup2.hkl

e-69-0o988-Isup2.hkl^{(155.5KB, hkl)}

Click here for additional data file.^{(6.9KB, cml)}

Supplementary material file. DOI: 10.1107/S1600536813014104/zp2005Isup3.cml

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

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

Cg3 and Cg4 are the centroids of the C4–C9 and C10–C15 rings, respectively.

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C17A—H17A⋯N1ⁱ	0.95	2.45	3.246 (8)	141
C21A—H21A⋯Cg3ⁱⁱ	0.95	2.98	3.888 (5)	160
C21B—H21B⋯Cg4ⁱ	0.95	2.99	3.914 (4)	163

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

Acknowledgments

Manchester Metropolitan University, Erciyes University and Granada University are gratefully acknowledged for supporting this study. The authors also thank José Romero Garzón, Centro de Instrumentación Científica, Universidad de Granada, for the data collection.

supplementary crystallographic information

Comment

The substituted imidazole derivatives are valuable in treatment of many systemic microbial infections and exhibit different types of pharmacological and biological activities (Kumar 2010). A number of substituted imidazoles, including clotrimazole, are selective inhibitors of nitric oxide synthase, which makes them interesting drug targets in inflammation, neurodegenerative diseases and tumors of the nervous system (Bogle et al., 1994; Castaño et al., 2008). Imidazoles also belong to the class of azole antifungals (Banfi et al., 2006), which includes 1-vinyl imidazole, ketoconazole, miconazole, and clotrimazole. In this aspect we have prepared a series of tetrasubstituted imidazoles including the title compound as potential bio-active precursors. Herein, we report the single-crystal X-ray structure of 2,4,5-Triphenyl-1-(prop-2-en-1-yl)-1H-imidazole (I).

In the title compound (I), (Fig. 1), the two parts of the disordered imidazole ring adopt an envelope conformation [the puckering parameters (Cremer & Pople, 1975) are Q(2) = 0.076 (3) Å, φ(2) = 357 (4) ° for (N1/N2A/C1/C2A/C3), and Q(2) = 0.146 (4) Å, φ(2) = 180 (3) ° for (N1/N2B/C1/C2B/C3)]. The phenyl rings (C4–C9, C10–C15, C16A–C21A and C16B–C21B) makes dihedral angles of 35.91 (7), 18.14 (17), 85.0 (2) and 87.8 (2)°, respectively, with the mean plane of the imadazole ring (N1/N2A/C1/C2A/C3) and the corresponding angles are 18.8 (3), 35.3 (2), 85.7 (3) and 83.6 (3)°, respectively, for (N1/N2B/C1/C2B/C3). The bond lengths in (I) are within normal ranges and are comparable with those reported for the similar structures (Mohamed et al., 2013a,b; Akkurt et al., 2013).

In the crystal structure, molecules are linked by intermolecular C—H···N hydrogen bonds (Table 1, Fig. 2). In addition, C—H···π interactions contribute to the stabilization of the crystal packing.

Experimental

The title compound was synthesized according to our reported method (Mohamed et al. 2013a) in 83% yield. Colourless plates suitable for X-ray analyses were obtained by slow evaporation of a solution of (I) in ethanol, m.p. 377–379 K.