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

Mehmet Akkurt; Shaaban K Mohamed; Adel A Marzouk; Antar A Abdelhamid; Francisco Santoyo-Gonzalez

doi:10.1107/S1600536813015936

. 2013 Jun 15;69(Pt 7):o1098–o1099. doi: 10.1107/S1600536813015936

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

Mehmet Akkurt ^a, Shaaban K Mohamed ^b,^c, Adel A Marzouk ^d,^e, Antar A Abdelhamid ^f,^*, Francisco Santoyo-Gonzalez ^g

PMCID: PMC3770375 PMID: 24046660

Abstract

In the title compound, C₂₆H₂₄N₂O₂, the two phenyl and the 2,5-dimethoxyphenyl rings are inclined to the imidazole ring at dihedral angles of 30.38 (8), 56.59 (9) and 73.11 (9)°, respectively. In the crystal, molecules are linked by pairs of C—H⋯O interactions into centrosymmetric dimers with graph-set notation R ₂ ²(8). C—H⋯π interactions are also observed.

Related literature

For chemical properties and applications of imidazoles with an unsaturated side chain, see, for example: Koszykowska et al. (2009 ▶); Berezin et al. (2009 ▶); Rambo et al. (2010 ▶); Min et al. (2006 ▶). For similar structures, see: Akkurt et al. (2013a ▶,b ▶); Mohamed et al. (2013a ▶,b ▶). For hydrogen-bond motifs, see: Bernstein et al. (1995 ▶).

Experimental

Crystal data

C₂₆H₂₄N₂O₂
M _r = 396.47
Triclinic,
a = 8.3117 (14) Å
b = 10.5217 (17) Å
c = 13.425 (2) Å
α = 105.938 (2)°
β = 101.846 (2)°
γ = 107.772 (2)°
V = 1020.1 (3) Å³
Z = 2
Mo Kα radiation
μ = 0.08 mm⁻¹
T = 100 K
0.26 × 0.16 × 0.08 mm

Data collection

Bruker SMART APEX CCD area-detector diffractometer
Absorption correction: multi-scan (SADABS; Sheldrick, 2004 ▶) T _min = 0.979, T _max = 0.993
11527 measured reflections
4193 independent reflections
3184 reflections with I > 2σ(I)
R _int = 0.036

Refinement

R[F ² > 2σ(F ²)] = 0.047
wR(F ²) = 0.125
S = 1.05
4193 reflections
273 parameters
H-atom parameters constrained
Δρ_max = 0.23 e Å⁻³
Δρ_min = −0.26 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/S1600536813015936/bx2444sup1.cif

e-69-o1098-sup1.cif^{(30KB, cif)}

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536813015936/bx2444Isup2.hkl

e-69-o1098-Isup2.hkl^{(205.4KB, hkl)}

Click here for additional data file.^{(8.1KB, cml)}

Supplementary material file. DOI: 10.1107/S1600536813015936/bx2444Isup3.cml

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

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

Cg1, Cg2 and Cg4 are the centroids of the N1/N2/C1–C3, C4–C9 and C19–C24 rings, respectively.

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C20—H20⋯O1ⁱ	0.95	2.54	3.354 (2)	143
C14—H14⋯Cg2ⁱⁱ	0.95	2.63	3.4083 (19)	139
C25—H25B⋯Cg1ⁱⁱⁱ	0.98	2.84	3.6337 (19)	139
C26—H26C⋯Cg4^iv	0.98	2.95	3.908 (2)	166

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

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

Recently, much attention has been devoted to vinyl and allyl N-substituted imidazole compunds due to their interesting properties and high reactivities. Such compounds in addition to threir flourecent properties (Berezin et al., 2009; Rambo et al., 2010) they can polymerize to obtain chromophoric polymers (Koszykowska et al., 2009). In addition their quaternery salts are acting as ionic catalists (Min et al., 2006) which are widely used in green chemistry applications. In this context the title compound has been synthesized among series of allyl imidazole derivatives and herein we report its crystal structure.

In the title compound (I, Fig. 1), the two phenyl (C4–C9 and C10–C15) and 2-(2,5-dimethoxyphenyl) (C19–C24) rings are inclined to the N1/N2/C1–C3 imidazole ring at angles of 30.38 (8), 56.59 (9) and 73.11 (9)°, respectively. All bond lengths and angles are normal and are corresponding to those reported in a similar structure (Akkurt et al., 2013a,b; Mohamed et al., 2013a,b). In the crystal the molecules are linked by C— H··· O interactions into centrosymmetric dimers with graph-set notation R₂²(8) (Bernstein et al., 1995).C—H···π interactions are also observed,Table 1, Fig2.

Experimental

The title compound was synthesized according to our reported method (Mohamed et al. 2013a) in 85% yield. Colourless prisms suitable for X-ray analyses were obtained by slow evaporation of a solution of (I) in ethanol, m.p. 471–473 K.