2-(2-Methyl-5-nitro-1H-imidazol-1-yl)ethyl 4-fluorobenzoate

In the title compound, C13H12FN3O4, the dihedral angle between the benzene and imidazole rings is 32.77 (12)°. In the crystal, molecules are linked into a three-dimensional network by C—H⋯O hydrogen bonds.

In the title compound, C 13 H 12 FN 3 O 4 , the dihedral angle between the benzene and imidazole rings is 32.77 (12) . In the crystal, molecules are linked into a three-dimensional network by C-HÁ Á ÁO hydrogen bonds.   Table 1 Hydrogen-bond geometry (Å , ).

Comment
The title compound is a derivative of well known broad spectrum antibiotic metronidazole, commonly known as Flagyl.
A number of metronidazole derivatives have been synthesized to evaluate their biological potentials, such as antibacterial (Atia, 2009;Dubey et al., 2009;Beena et al., 2009;Bowden & Izadi, 1998), anticancer (Qian et al., 2010, and H. pylori urease inhibitors (Mao et al., 2009). These properties of metronidazole derivatives attracted the attention of synthetic and medicinal chemists to further explore their potential against different diseases. In present study, metronidazole ester derivative was prepared in a cost effective manner to evaluate its antiglycation potential.
The reaction was quenched with 20 ml HCl (0.5 M) and then basified with sat.NaHCO 3 . It was extracted with dichloromethane and evaporated in vacuo to obtain crude product. The mixture of crude product was purified by using silica gel chromatography (EtOAc:hexane, 3.0:7.0 to 7.0:3.0) which afforded compound 1 in 85% yield. Recrystallization from the slow evaporation of dichloromethane afforded pure crystals found suitable for single-crystal X-ray diffraction studies. All chemicals were purchased from Sigma-Aldrich.

Refinement
H atoms on methyl, methylene and methine groups were positioned geometrically with C-H = 0.96, 0.97 and 0.93 Å, respectively, and constrained to ride on their parent atoms with U iso (H) = 1.2U eq (CH and CH 2 ) and 1.5U eq (CH 3 ). A rotating group model was applied to the methyl groups. In the absence of significant anomalous scattering effects, 952 Friedel pairs were merged before the final refinement.  The molecular structure of the title compound with displacement ellipsoids drawn at 30% probability level.

Figure 2
The crystal packing view of the title compound.

Special details
Geometry. All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell e.s.d.'s are taken into account individually in the estimation of e.s.d.'s in distances, angles and torsion angles; correlations between e.s.d.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell e.s.d.'s is used for estimating e.s.d.'s involving l.s. planes. Refinement. Refinement of F 2 against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F 2 , conventional R-factors R are based on F, with F set to zero for negative F 2 . The threshold expression of F 2 > σ(F 2 ) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F 2 are statistically about twice as large as those based on F, and R-factors based on ALL data will be even larger.