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

Sammer Yousuf; Aurang Zeb; Fatima Z Basha

doi:10.1107/S1600536812006319

. 2012 Mar 3;68(Pt 4):o952. doi: 10.1107/S1600536812006319

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

Sammer Yousuf ^a,^*, Aurang Zeb ^a, Fatima Z Basha ^a

PMCID: PMC3343933 PMID: 22590014

Abstract

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.

Related literature

For biological activities of metronidazole derivatives, see: Atia (2009 ▶); Beena et al. (2009 ▶); Bowden & Izadi (1998 ▶); Dubey et al. (2009 ▶); Mao et al. (2009 ▶); Qian et al. (2010 ▶).

Experimental

Crystal data

C₁₃H₁₂FN₃O₄
M _r = 293.26
Monoclinic,
a = 8.9669 (12) Å
b = 18.784 (2) Å
c = 7.8288 (10) Å
β = 99.684 (3)°
V = 1299.9 (3) Å³
Z = 4
Mo Kα radiation
μ = 0.12 mm⁻¹
T = 273 K
0.50 × 0.29 × 0.16 mm

Data collection

Bruker SMART APEX CCD diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2000 ▶) T _min = 0.941, T _max = 0.981
3782 measured reflections
1186 independent reflections
1150 reflections with I > 2σ(I)
R _int = 0.022

Refinement

R[F ² > 2σ(F ²)] = 0.032
wR(F ²) = 0.088
S = 1.06
1186 reflections
192 parameters
2 restraints
H-atom parameters constrained
Δρ_max = 0.15 e Å⁻³
Δρ_min = −0.11 e Å⁻³

Data collection: SMART (Bruker, 2000 ▶); cell refinement: SAINT (Bruker, 2000 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: SHELXTL (Sheldrick, 2008 ▶); software used to prepare material for publication: SHELXTL, PARST (Nardelli, 1995 ▶) and PLATON (Spek, 2009 ▶).

Supplementary Material

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S1600536812006319/is5064sup1.cif

e-68-0o952-sup1.cif^{(17.9KB, cif)}

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536812006319/is5064Isup2.hkl

e-68-0o952-Isup2.hkl^{(58.7KB, hkl)}

Supplementary material file. DOI: 10.1107/S1600536812006319/is5064Isup3.cml

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

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

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C1—H1A⋯O1ⁱ	0.93	2.45	3.378 (3)	172
C2—H2B⋯O3ⁱⁱ	0.93	2.46	3.356 (4)	162

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

supplementary crystallographic information

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.

In the title compound, the benzene (C1–C6) and imidazole (N1/C10/C11/N2/C12) rings are almost planar (Fig. 1) with a dihedral angle of 32.77 (12)° between the mean planes. The bond lengths and angles are within the normal ranges. C1—H1A···O1ⁱ and C2—H2B···O3ⁱⁱ hydrogen bonds (symmetry codes as in Table 1) play important roles in stabilizing the crystal structure by forming a three-dimensional network (Fig. 2).

Experimental

The synthesis of title compounds 1 was achieved by reacting metronidazole (171 mg, 1.0 mmole) with 4-fluorobenzoic acid (1.2 equiv.) in the presence of dicyclohexylcarbodiimide (245 mg, 1.2 mmole) and 4-dimethylaminopyridine (0.35 mmole) in dichloromethane (10 ml) at room temperature for 40–45 h. The progress of reaction was monitored by TLC. The reaction was quenched with 20 ml HCl (0.5 M) and then basified with sat.NaHCO₃. 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.