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

Shaaban K Mohamed; Mehmet Akkurt; Adel A E Marzouk; Francisco Santoyo-Gonzalez; Mahmoud A A Elremaily

doi:10.1107/S1600536813012592

. 2013 May 11;69(Pt 6):o875–o876. doi: 10.1107/S1600536813012592

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

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

PMCID: PMC3685034 PMID: 23795053

Abstract

The title compound, C₂₄H₁₉ClN₂, crystallizes with two independent molecules in the asymmetric unit. The prop-2-enyl substituents on the imidazole rings adopt similar conformations in the two molecules. The 4-and 5-substituted phenyl rings and the benzene ring make dihedral angles of 67.06 (8), 5.61 (8) and 41.09 (8)°, respectively, with the imadazole ring in one molecule and 71.53 (8), 28.85 (8) and 41.87 (8)°, respectively, in the other. The crystal structure features C—H⋯π interactions and weak π–π stacking interactions [centroid–centroid distances = 3.6937 (10) and 4.0232 (10) Å] between the chlorophenyl rings, which form a three-dimensional supramolecular structure.

Related literature

For pharmaceutical properties of imidazoles and imidazole-containing compounds, see, for example: Roman et al. (2007 ▶); Nanterment et al. (2004 ▶); Congiu et al. (2008 ▶); Venkatesan et al. (2008 ▶); Bhatnagar et al. (2011 ▶); Puratchikody & Doble (2007 ▶). For similar structures, see: Mohamed et al. (2013 ▶); Akkurt et al. (2013 ▶).

Experimental

Crystal data

C₂₄H₁₉ClN₂
M _r = 370.86
Triclinic,
a = 10.0916 (7) Å
b = 13.1386 (9) Å
c = 15.6155 (10) Å
α = 72.924 (1)°
β = 86.849 (1)°
γ = 71.830 (1)°
V = 1879.0 (2) Å³
Z = 4
Mo Kα radiation
μ = 0.21 mm⁻¹
T = 100 K
0.57 × 0.33 × 0.28 mm

Data collection

Bruker SMART APEX CCD area-detector diffractometer
Absorption correction: multi-scan (SADABS; Sheldrick, 2004 ▶) T _min = 0.919, T _max = 0.942
20791 measured reflections
7718 independent reflections
6764 reflections with I > 2σ(I)
R _int = 0.023

Refinement

R[F ² > 2σ(F ²)] = 0.041
wR(F ²) = 0.106
S = 1.07
7718 reflections
487 parameters
H-atom parameters constrained
Δρ_max = 0.34 e Å⁻³
Δρ_min = −0.23 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.^{(44.7KB, cif)}

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S1600536813012592/hg5314sup1.cif

e-69-0o875-sup1.cif^{(44.7KB, cif)}

Click here for additional data file.^{(377.6KB, hkl)}

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536813012592/hg5314Isup2.hkl

e-69-0o875-Isup2.hkl^{(377.6KB, hkl)}

Click here for additional data file.^{(7KB, cml)}

Supplementary material file. DOI: 10.1107/S1600536813012592/hg5314Isup3.cml

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

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

Cg2, Cg4 and Cg8 are the centroids of the C4–C9, C19–C24 and C43–C48 rings, respectively.

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C5—H5⋯Cg4ⁱ	0.95	2.76	3.5968 (17)	147
C11—H11⋯Cg8ⁱⁱ	0.95	2.83	3.5879 (19)	137
C33—H33⋯Cg2ⁱⁱⁱ	0.95	2.89	3.8217 (18)	166

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

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

Imidazoles have been intensivley reported to serve as usefull building blocks for synthesis of diverse class of bioactive molecules. In addition imidazole comtaining compounds exhibited a wide spectrum of pharmaceutical properties such as pesticides, fungicides, antibacterial anti-inflammatory, anti-tubercular, anti-diabetic, antimalarial and antitumour (Roman et al., 2007; Nanterment et al., 2004; Congiu et al., 2008; Venkatesan et al., 2008; Bhatnagar et al., 2011; Puratchikody & Doble 2007). In this aspect and further to our study on synthesis of tetrasubstituted imidazoles as potential bioactive molecules, we herein report the crystal structure of the title compound.

As seen in the Fig. 1, the title compound contains two independent molecules, 1 (with Cl1) and 2 (with Cl2), in the asymmetric unit. The prop-2-ene substituents on the imidazole rings adopt similar conformations in molecules 1 and 2. The 4-and 5-substituted phenyl rings (C4–C9 and C19–C24) and the benzene ring (C13–C18) attached to the atom Cl1 makes dihedral angles of 67.06 (8), 5.61 (8) and 41.09 (8)°, respectively, with the imadazole ring (N1/N2/C1–C3) of molecule 1 and the corresponding angles are A/B = 71.53 (8), A/C = 28.85 (8) and A/D = 41.87 (8)°, respectively, in molecule 2; where A (N3/N4/C25–C27), B (C28–C33), C (C43–C48) and D (C37–C42). All bond lengths are normal and are comparable with those reported for the similar structures (Mohamed et al., 2013; Akkurt et al., 2013).

The crystal structure is stabilized by C—H···π interactions (Table 1) and weak π-π stacking interactions [Cg3···Cg3 (-x, -y, 1 - z) = 3.6937 (10) Å and Cg7···Cg7 (-x, 1 - y, 1 - z) = 4.0232 (10) Å; where Cg3 and Cg7 are the centroids of the C13–C18 and C37–C42 benzene rings respectively, which are attached to the Cl1 and Cl2 atoms]. Fig. 2 shows the packing diagram of (I) along the a axis.

Experimental

The title compound was prepared, according to our reported method (Mohamed et al., 2013) in 81% yield. Suitable single crystals were obtained by slow evaporation of a solution in ethanol, m.p. 305–307 K.