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

S Rosepriya; A Thiruvalluvar; K Saravanan; J Jayabharathi; Ray J Butcher

doi:10.1107/S1600536811055012

. 2012 Jan 7;68(Pt 2):o256. doi: 10.1107/S1600536811055012

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

S Rosepriya ^a, A Thiruvalluvar ^a,^*, K Saravanan ^b, J Jayabharathi ^b, Ray J Butcher ^c

PMCID: PMC3274949 PMID: 22346902

Abstract

In the title compound, C₁₉H₁₉FN₂O₂, the imidazole ring is essentially planar [maximum deviation = 0.0030 (8) Å] and makes dihedral angles of 66.45 (7) and 29.98 (7)° with the benzene rings attached to the ring N and C atoms, respectively. The dihedral angle between the two benzene rings is 64.79 (7)°. A C—H⋯π interaction is found in the crystal structure. The two methoxy groups were found to be disordered over two sets of sites with occupancy factors of 0.803 (4) and 0.197 (4). The F atom is disordered over two sites with occupancy factors of 0.929 (4) and 0.071 (4).

Related literature

For general background to the use of imidazole derivatives as drugs, see: Dooley et al. (1992 ▶); Jackson et al. (2000 ▶); Banfi et al. (2006 ▶). For a related structure and applications of imidazole derivatives, see: Rosepriya et al. (2011 ▶).

Experimental

Crystal data

C₁₉H₁₉FN₂O₂
M _r = 326.36
Monoclinic,
a = 6.9654 (1) Å
b = 17.8520 (3) Å
c = 13.7121 (3) Å
β = 97.833 (2)°
V = 1689.14 (5) Å³
Z = 4
Cu Kα radiation
μ = 0.75 mm⁻¹
T = 295 K
0.47 × 0.38 × 0.16 mm

Data collection

Oxford Diffraction Xcalibur Ruby Gemini diffractometer
Absorption correction: multi-scan CrysAlis PRO (Oxford Diffraction, 2010 ▶) T _min = 0.558, T _max = 1.000
7744 measured reflections
3533 independent reflections
2723 reflections with I > 2σ(I)
R _int = 0.024

Refinement

R[F ² > 2σ(F ²)] = 0.046
wR(F ²) = 0.138
S = 1.06
3533 reflections
240 parameters
H-atom parameters constrained
Δρ_max = 0.21 e Å⁻³
Δρ_min = −0.18 e Å⁻³

Data collection: CrysAlis PRO (Oxford Diffraction, 2010 ▶); cell refinement: CrysAlis PRO; data reduction: CrysAlis PRO; 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 datablock(s) global, I. DOI: 10.1107/S1600536811055012/hg5156sup1.cif

e-68-0o256-sup1.cif^{(23.1KB, cif)}

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536811055012/hg5156Isup2.hkl

e-68-0o256-Isup2.hkl^{(169.8KB, hkl)}

Supplementary material file. DOI: 10.1107/S1600536811055012/hg5156Isup3.cdx

Supplementary material file. DOI: 10.1107/S1600536811055012/hg5156Isup4.cml

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

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

Cg1 is the centroid of the N1/C2/N3/C4/C5 ring.

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C23—H23⋯Cg1ⁱ	0.93	2.99	3.8714 (16)	159

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Symmetry code: (i) Inline graphic .

Acknowledgments

JJ is thankful to the Department of Science and Technology [No. SR/S1/IC-07/2007] and the University Grants Commission [F. No. 36–21/2008 (SR)] for providing funding for this research work. RJB acknowledges the NSF MRI program (grant No. CHE-0619278) for funds to purchase the X-ray diffractometer.

supplementary crystallographic information

Comment

For multidrug-resistant Tuberculosis (Dooley et al.,(1992)), antifungal and antimycobacterial activity (Banfi et al. 2006), and bactericidal effects (Jackson et al. 2000), the use of imidazole based compounds were reported. Rosepriya et al. 2011 have reported the crystal structure of 1-(3,5-Dimethylphenyl)-2-(4-fluorophenyl)-4,5-dimethyl-1H-imidazole. As part of our research (Rosepriya et al. 2011), we have synthesized the title compound (I) and report its crystal structure here.

In the title compound, Fig. 1, C₁₉H₁₉FN₂O₂, the imidazole ring is essentially planar [maximum deviation of 0.0030 (8) Å for C4]. The imidazole ring makes dihedral angles of 66.45 (7) and 29.98 (7)° with the benzene rings attached to nitrogen and carbon, respectively. The dihedral angle between the two benzene rings is 64.79 (7)°. A C23—H23···π interaction involving the imidazole (N1,C2,N3,C4,C5) ring is found in the crystal structure (Table 1). The two methoxy groups at C13 and C15 were found to be disordered over two positions with occupancy factors of 0.803 (4) and 0.197 (4). The F atom at C24 is disordered over two positions with occupancy factors of 0.929 (4) and 0.071 (4).

Experimental

To pure butane-2,3-dione (1.48 g, 15 mmol) in ethanol (10 ml), 3,5-dimethoxyaniline (2.29 g, 15 mmol), ammonium acetate (1.15 g, 15 mmol) and 4-fluorobenzaldehyde (1.8 g, 15 mmol) was added over 1 hr with the temperature maintained 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: 2.20 g (45%). Crystals suitable for X-ray diffraction studies were grown by slow solvent evaporation of a solution of the compound in dichloromethane.