5-(4-Fluoro­phen­yl)-5-methyl­imidazolidine-2,4-dione

M Kaleem Kashif; Abid Hussain; M Khawar Rauf; Masahiro Ebihara; Shahid Hameed

doi:10.1107/S1600536807067803

. 2008 Jan 16;64(Pt 2):o444. doi: 10.1107/S1600536807067803

5-(4-Fluorophenyl)-5-methylimidazolidine-2,4-dione

M Kaleem Kashif ^a, Abid Hussain ^a, M Khawar Rauf ^b, Masahiro Ebihara ^b, Shahid Hameed ^a,^*

PMCID: PMC2960434 PMID: 21201471

Abstract

In the title compound, C₁₀H₉FN₂O₂, the dihedral angle between the hydantoin unit and the benzene ring is 65.55 (5)°. The atoms in the hydantoin ring are coplanar, with a mean deviation of 0.015 Å and a maximum deviation of 0.075 (2) Å for one carbonyl O atom. N—H⋯O hydrogen bonds link the molecules into one-dimensional chains, with one carbonyl group acting as a bifurcated acceptor and the other accepting no hydrogen bonds.

Related literature

For related literature, see: Ahmad et al. (2000 ▶, 2002 ▶); Balavoine et al. (2007 ▶); Mullica et al. (1998 ▶); Park et al. (2007 ▶); Rajic et al. (2006 ▶); Sheppeck et al. (2007 ▶).

Experimental

Crystal data

C₁₀H₉FN₂O₂
M _r = 208.19
Orthorhombic,
a = 7.096 (2) Å
b = 11.348 (3) Å
c = 22.661 (7) Å
V = 1824.7 (10) Å³
Z = 8
Mo Kα radiation
μ = 0.12 mm⁻¹
T = 123 (2) K
0.34 × 0.30 × 0.20 mm

Data collection

Rigaku Mercury CCD diffractometer
Absorption correction: none
13516 measured reflections
2083 independent reflections
2054 reflections with I > 2σ(I)
R _int = 0.026

Refinement

R[F ² > 2σ(F ²)] = 0.045
wR(F ²) = 0.094
S = 1.22
2083 reflections
145 parameters
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.31 e Å⁻³
Δρ_min = −0.16 e Å⁻³

Data collection: CrystalClear (Molecular Structure Corporation & Rigaku, 2001 ▶); cell refinement: CrystalClear; data reduction: TEXSAN (Rigaku/MSC, 2004 ▶); program(s) used to solve structure: SIR97 (Altomare et al., 1999 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997 ▶); molecular graphics: ORTEPII (Johnson, 1976 ▶); software used to prepare material for publication: SHELXL97 and TEXSAN.

Supplementary Material

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536807067803/bi2269sup1.cif

e-64-0o444-sup1.cif^{(15.5KB, cif)}

Structure factors: contains datablocks I. DOI: 10.1107/S1600536807067803/bi2269Isup2.hkl

e-64-0o444-Isup2.hkl^{(102.5KB, hkl)}

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
N1—H1⋯O1ⁱ	0.88 (2)	2.04 (2)	2.8834 (17)	160.5 (18)
N2—H2⋯O1ⁱⁱ	0.89 (2)	1.96 (2)	2.8318 (17)	165.9 (17)

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

Acknowledgments

MKR is grateful to the Higher Education Commission of Pakistan for financial support under the International Support Initiative Program for a Doctoral Fellowship at Gifu University, Japan.

supplementary crystallographic information

Comment

Active research is being carried out in this laboratory on the synthesis of sulfonyl cyclic ureas and their evaluation as hypoglycemic agents (Ahmad et al., 2002; Ahmad et al., 2000). Imidazolidine-2,4-diones, a class of cyclic urea molecules, exhibit diverse biological activities like anti-cancer (Sheppeck et al., 2007), anti-viral (Rajic et al., 2006), COX-2 inhibitors (Park et al., 2007) and hormone receptor antagonists (Balavoine et al., 2007). The title compound (Fig. 1) was synthesized as an intermediate for onward conversion to sulfonyl derivatives for hypoglycemic assay. It contains a hydantoin ring attached to a methyl and p-flourophenyl group at the chiral centre C1. All bond distances are in agreement with experimental values found in similar compounds. The atoms in the hydantoin ring are planar as expected (Mullica et al., 1998) with a mean standard deviation of 0.015 Å. The C2—O1 and C3—O2 bond distances are 1.2320 (17) Å and 1.2080 (17) Å, respectively, which are close to the standard value for C?O (1.20 Å). The dihedral angle subtended by the p-flourophenyl group at the chiral centre C(1) is 65.55 (5)°.

Experimental

4-Fluoroacetophenone (0.1 mol) and ammonium carbonate (0.6 mol) were placed in a 100 ml round bottom flask. Potassium cyanide (0.1 mol) was dissolved in aqueous ethanol (60%) and added to the reaction flask. The mixture was heated on an oil bath at 328–333 K until the reaction was completed (monitored by TLC). After cooling to room temperature, the reaction mixture was concentrated and acidified using conc. HCl. The resulting precipitate was filtered, dissolved in saturated NaOH(aq) solution and extracted with diethyl ether (25 ml). The aqueous layer was acidified to precipitate the title compound, which was filtered, dried and recrystallized from ethanol/water. Yield: 75%; m.p. 485–488 K; R_f (pet. ether/ethyl acetate 1:2) 0.58.

IR (KBr, ν_max, cm^-1): 3412, 3245, 3058, 2989, 1773, 1719, 1602, 1378, 1274, 838; ¹H-NMR (acetone-d6) δ: 1.80 (3H, s), 7.18 (2H, m), 7.64 (2H, m), 7.71 (1H, bs), 9.72 (1H, bs); EIMS (m/z, %): 208 (M⁺, 20), 193 (65), 165 (5), 137 (36), 122 (100), 95 (25); Elemental analysis calculated: C 57.69, H 4.36, N 13.46; found: C 57.62, H 4.38, N 13.60%.