1-(3,5-Dimethyl­phenyl)-2-(4-fluoro­phenyl)-4,5-dimethyl-1H-imidazole

S Rosepriya; A Thiruvalluvar; J Jayabharathi; N Srinivasan; R J Butcher; J P Jasinski; J A Golen

doi:10.1107/S1600536811012098

. 2011 Apr 7;67(Pt 5):o1065. doi: 10.1107/S1600536811012098

1-(3,5-Dimethylphenyl)-2-(4-fluorophenyl)-4,5-dimethyl-1H-imidazole

S Rosepriya ^a, A Thiruvalluvar ^a,^*, J Jayabharathi ^b, N Srinivasan ^b, R J Butcher ^c, J P Jasinski ^d, J A Golen ^d

PMCID: PMC3089216 PMID: 21754391

Abstract

In the title compound, C₁₉H₁₉FN₂, the imidazole ring is essentially planar [maximum deviation of 0.0015 (9) Å] and makes dihedral angles of 77.61 (9) and 26.93 (10)° with the benzene rings attached to nitrogen and carbon, respectively. The dihedral angle between the two benzene rings is 78.84 (8)°. A C—H⋯π interaction is found in the crystal structure.

Related literature

For related structures and applications of imidazole derivatives, see: Gayathri et al. (2010 ▶); Rosepriya et al. (2011 ▶).

Experimental

Crystal data

C₁₉H₁₉FN₂
M _r = 294.36
Triclinic,
a = 8.4226 (10) Å
b = 9.5572 (10) Å
c = 11.0351 (11) Å
α = 105.423 (9)°
β = 105.677 (9)°
γ = 95.781 (9)°
V = 810.07 (17) Å³
Z = 2
Cu Kα radiation
μ = 0.63 mm⁻¹
T = 170 K
0.25 × 0.20 × 0.15 mm

Data collection

Oxford Diffraction Xcalibur Eos Gemini diffractometer
Absorption correction: multi-scan (CrysAlis RED; Oxford Diffraction, 2010 ▶) T _min = 0.858, T _max = 0.911
5121 measured reflections
3054 independent reflections
2771 reflections with I > 2σ(I)
R _int = 0.011

Refinement

R[F ² > 2σ(F ²)] = 0.052
wR(F ²) = 0.159
S = 1.07
3054 reflections
203 parameters
H-atom parameters constrained
Δρ_max = 0.31 e Å⁻³
Δρ_min = −0.23 e Å⁻³

Data collection: CrysAlis PRO (Oxford Diffraction, 2010 ▶); cell refinement: CrysAlis PRO; data reduction: CrysAlis RED (Oxford Diffraction, 2010 ▶); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: ORTEP-3 (Farrugia, 1997 ▶); software used to prepare material for publication: PLATON (Spek, 2009 ▶).

Supplementary Material

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536811012098/hg5018sup1.cif

e-67-o1065-sup1.cif^{(19.9KB, cif)}

Structure factors: contains datablocks I. DOI: 10.1107/S1600536811012098/hg5018Isup2.hkl

e-67-o1065-Isup2.hkl^{(146.8KB, hkl)}

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

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

Cg3 is the centroid of the C21–C26 ring.

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C12—H12⋯Cg3ⁱ	0.95	2.86	3.7969 (19)	169

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Symmetry code: (i) Inline graphic .

Acknowledgments

JPJ acknowledges the NSF–MRI program (grant No. CHE1039027) for funds to purchase the X-ray diffractometer.

supplementary crystallographic information

Comment

Rosepriya et al. (2011) have reported the crystal structure of 1,2-Diphenyl-1H-imidazo[4,5-f][1,10]phenanthroline. As part of our research (Gayathri et al., (2010)), we have synthesized the title compound (I) and report its crystal structure here. Since our group doing the research in organic light emitting devices, we are interested to use the title compound as ligand for synthesizing Ir(III) complexes.

In the title compound (Fig. 1), C₁₉H₁₉FN₂, the imidazole ring is essentially planar [maximum deviation of 0.0015 (9) Å for C4]. The imidazole ring makes dihedral angles of 77.61 (9) and 26.93 (10)° with the benzene rings attached to N1 and C2, respectively. The dihedral angle between the two benzene rings is 78.84 (8)°. A C12—H12···π interaction involving (C21—C26) ring is found in the crystal structure (Table 1).

Experimental

To pure butane-2,3-dione (1.48 g, 15 mmol) in ethanol (10 ml), 3,5-xylidine (1.8 g, 15 mmol), ammonium acetate (1.15 g, 15 mmol) and 4-fluorobenzaldehyde (1.7 g, 15 mmol) was added about 1 h by maintaining the temperature at 333 K. The reaction mixture was refluxed for 7 days and extracted with dichloromethane. The solid separated was purified by column chromatography using hexane: ethyl acetate as the eluent. Yield: 2.1 g (48%). Crystals suitable for X-ray diffraction studies were grown by slow solvent evaporation of a solution of the compound in dichloromethane.