4-(1-Allyl-4,5-diphenyl-1H-imidazol-2-yl)-N,N-dimethyl­aniline

Mehmet Akkurt; Frank R Fronczek; Shaaban K Mohamed; Avtandil H Talybov; Adel A E Marzouk; Antar A Abdelhamid

doi:10.1107/S1600536813006326

. 2013 Mar 9;69(Pt 4):o527–o528. doi: 10.1107/S1600536813006326

4-(1-Allyl-4,5-diphenyl-1H-imidazol-2-yl)-N,N-dimethylaniline

Mehmet Akkurt ^a, Frank R Fronczek ^b, Shaaban K Mohamed ^c,^d,^*, Avtandil H Talybov ^e, Adel A E Marzouk ^e,^f, Antar A Abdelhamid ^d

PMCID: PMC3629582 PMID: 23634069

Abstract

The title compound, C₂₆H₂₅N₃, crystallizes with four independent molecules, 1–4, in the asymmetric unit of the triclinic unit cell. The allyl substituents on the imidazole rings adopt similar conformations in all four molecules. The imadazole and the 4-and 5-substituted phenyl rings of two pairs of molecules in the asymmetric unit stack parallel to (110). In contrast, the dimethylaniline systems in these pairs of molecules are almost normal to one another, with dihedral angles of 85.84 (10) and 85.65 (10)° between the benzene rings of the two dimethylaniline fragments of molecules 1 and 2, and 3 and 4, respectively. The crystal structure features an extensive series of C—H⋯π interactions that link the molecules into undulating rows along the c axis. The crystal studied was a pseudo-merohedral twin with twin law [-100, 0-10, 111] and the BASF parameter refined to 0.513 (3).

Related literature

For the synthesis and bioactivity of related heterocyclic molecules, see: El-Sawy et al. (2012 ▶); Issac et al. (2012 ▶); Mohamed, Abdelhamid et al. (2012 ▶); Soliman et al. (2012 ▶). For the synthesis of a similar imidazole derivative, see: Mohamed, Akkurt et al. (2012 ▶). For bond-length data, see: Allen et al. (1987 ▶).

Experimental

Crystal data

C₂₆H₂₅N₃
M _r = 379.49
Triclinic,
a = 9.4259 (7) Å
b = 10.2028 (7) Å
c = 44.721 (3) Å
α = 94.711 (2)°
β = 94.096 (2)°
γ = 107.359 (2)°
V = 4070.2 (5) Å³
Z = 8
Cu Kα radiation
μ = 0.57 mm⁻¹
T = 90 K
0.31 × 0.29 × 0.17 mm

Data collection

Bruker Kappa APEXII DUO diffractometer
Absorption correction: multi-scan (SADABS; Sheldrick, 2004 ▶) T _min = 0.844, T _max = 0.910
26145 measured reflections
13651 independent reflections
13253 reflections with I > 2σ(I)
R _int = 0.028

Refinement

R[F ² > 2σ(F ²)] = 0.043
wR(F ²) = 0.118
S = 1.03
13651 reflections
1054 parameters
72 restraints
H-atom parameters constrained
Δρ_max = 0.29 e Å⁻³
Δρ_min = −0.29 e Å⁻³

Data collection: APEX2 (Bruker, 2005 ▶); cell refinement: SAINT (Bruker, 2005 ▶); data reduction: SAINT (Bruker, 2005 ▶); 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.^{(84.5KB, cif)}

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S1600536813006326/sj5302sup1.cif

e-69-0o527-sup1.cif^{(84.5KB, cif)}

Click here for additional data file.^{(667.3KB, hkl)}

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536813006326/sj5302Isup2.hkl

e-69-0o527-Isup2.hkl^{(667.3KB, hkl)}

Click here for additional data file.^{(8KB, cml)}

Supplementary material file. DOI: 10.1107/S1600536813006326/sj5302Isup3.cml

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

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

Cg2, Cg8, Cg6, Cg4, Cg10, Cg16, Cg14 and Cg12 are the centroids of the C4–C9, C47–C52, C30–C35, C21–C26, C56–C61, C99–C104, C82–C87 and C73–C78 rings, respectively.

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C10—H10A⋯Cg2ⁱ	0.98	2.71	3.514 (3)	139
C16—H16⋯Cg8	0.95	2.47	3.328 (3)	151
C37—H37A⋯Cg6ⁱⁱ	0.98	2.77	3.600 (2)	142
C42—H42⋯Cg4ⁱⁱⁱ	0.95	2.49	3.345 (3)	150
C63—H63A⋯Cg10^iv	0.98	2.73	3.595 (2)	147
C68—H68⋯Cg16	0.95	2.59	3.390 (3)	142
C88—H88C⋯Cg14^v	0.98	2.74	3.509 (3)	136
C94—H94⋯Cg12ⁱⁱⁱ	0.95	2.48	3.340 (3)	150

Open in a new tab

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

Acknowledgments

Manchester Metropolitan University, Erciyes University and Louisiana State University are gratefully acknowledged for supporting this study.

supplementary crystallographic information

Comment

Further to our studies on the synthesis of bioactive heterocyclic molecules such as pyrimidines and fused imidazole compounds (Soliman et al., 2012), thiadiazoles (Issac et al. 2012), acridinones and xanthenones (Mohamed, Abdelhamid et al., 2012), benzoxazinones and quinazolinones (El-Sawy et al., 2012), we report herein the crystal and molecular structure of the title compound.

Figure 1 shows molecule 1 and the numbering scheme,while Figure 2 identifies the four independent molecules in the asymmetric unit. The allyl substituents on the imidazole rings adopt similar conformations in all four molecules. The –N—C(H₂)—C(H)—C(H₂) torsion angles of the prop-1-ene substituent on the imidazole rings are -8.5 (3), 0.4 (4), -9.6 (4) and -1.3 (4)°, respectively, for molecules 1···4. Bond lengths and angles of these four independent molecules are comparable with each other and the bond lengths are similar to values reported in the literature (Allen et al., 1987).

All four of the unique molecules depart significantly from planarity. In molecule 1 (with N1), the central imidazole ring forms dihedral angles of 26.84 (12), 67.62 (13) and 27.15 (13)° with the C4–C9 benzene and C15–C20 and C21–C26 phenyl rings, respectively [the corresponding angles in molecule 2 (with N4) are 57.03 (12), 66.12 (14) and 26.74 (14)°; molecule 3 (with N7) 57.70 (11), 64.34 (13) and 27.27 (13)°, and molecule 4 (with N10) 26.85 (12), 69.03 (13) and 26.83 (12)°].

The imadazole and the 4- and 5-substituted phenyl rings of adjacent pairs of molecules stack parallel to (110). In contrast, the dimethylaniline systems in these pairs of molecules are almost normal to one another with dihedral angles of 85.84 (10)° between the C5···C9 and C30···C35 benzene rings of molecules 1 and 2 and 85.65 (10)° between the C56···C61 and C82···C87 benzene rings of molecules 3 and 4.

The crystal structure is stabilized by an extensive series of C—H···π interactions (Table 1), that link the molecules into undulating rows along the c axis. Figure 3 shows the crystal packing of the title compound along the b axis.

Experimental

The title compound was prepared among series of imidazole derivatives according to our reported method (Mohamed, Akkurt et al., 2012). Suitable single crystals of (I) were obtained by the slow evaporation method using ethanol as a solvent. M.p. 403 – 405 K.