1-(4-Chloro­phenyl­sulfon­yl)-5-(4-fluoro­phen­yl)-5-methyl­imidazolidine-2,4-dione

Abid Hussain; Shahid Hameed; Helen Stoeckli-Evans

doi:10.1107/S160053680901037X

. 2009 Mar 25;65(Pt 4):o858–o859. doi: 10.1107/S160053680901037X

1-(4-Chlorophenylsulfonyl)-5-(4-fluorophenyl)-5-methylimidazolidine-2,4-dione

Abid Hussain ^a, Shahid Hameed ^a,^*, Helen Stoeckli-Evans ^b

PMCID: PMC2968985 PMID: 21582575

Abstract

The title compound, C₁₆H₁₂ClFN₂O₄S, crystallizes with two independent molecules (A and B) in the asymmetric unit. The two molecules are U-shaped with similar geometries and conformations. The mean planes through the benzene rings are inclined to one another by 6.07 (8)° in molecule A and 8.67 (8)° in molecule B. They are separated with a centroid–centroid distance of 3.9096 (10) Å in molecule A and 3.9118 (10) Å in molecule B. Molecules A and B lie adjacent to one another, with a centroid–centroid distance of 3.7592 (10) Å between the fluorophenyl ring of molecule A and the chlorophenylsulfonyl ring of molecule B and with a dihedral angle of 5.75 (8)° between the ring planes. In the crystal structure, A and B molecules are linked by N—H⋯O hydrogen bonds, forming centrosymmetric dimers. These dimers stack along the [110] direction and are linked by C—H⋯O and C—H⋯F interactions. There are also some short halide⋯halide contacts [Cl⋯F = 3.0499 (14) and 3.1224 (13) Å, and F⋯F = 3.0612 (17) Å].

Related literature

For the biological activity of imidazolidine-2,4-diones, see: Muccioli et al. (2006 ▶); Flosi et al. (2006 ▶). For the biological activity of sulfonyl derivatives of imidazolidine-2,4-diones, see: Kato, Nakayama, Mizota et al. (1991 ▶); Kato, Nakayama, Ohta et al. (1991 ▶); Ahmad et al. (2000 ▶, 2002 ▶); Kashif, Ahmad & Hameed (2008 ▶). For the crystal structure of 5-(4-fluorophenyl)-5-methylimidazolidine-2,4-dione, see: Kashif, Hussain et al. (2008 ▶).

Experimental

Crystal data

C₁₆H₁₂ClFN₂O₄S
M _r = 382.79
Triclinic,
a = 9.6959 (7) Å
b = 10.0066 (7) Å
c = 16.6269 (13) Å
α = 92.098 (6)°
β = 93.630 (6)°
γ = 103.056 (6)°
V = 1566.2 (2) Å³
Z = 4
Mo Kα radiation
μ = 0.41 mm⁻¹
T = 173 K
0.45 × 0.40 × 0.24 mm

Data collection

Stoe IPDS-2 diffractometer
Absorption correction: none
30542 measured reflections
8438 independent reflections
5836 reflections with I > 2σ(I)
R _int = 0.042

Refinement

R[F ² > 2σ(F ²)] = 0.037
wR(F ²) = 0.095
S = 0.89
8438 reflections
462 parameters
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.49 e Å⁻³
Δρ_min = −0.64 e Å⁻³

Data collection: X-AREA (Stoe & Cie, 2006 ▶); cell refinement: X-AREA; data reduction: X-RED32 (Stoe & Cie, 2006 ▶); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: PLATON (Spek, 2009 ▶); software used to prepare material for publication: SHELXL97.

Supplementary Material

Crystal structure: contains datablocks I, global. DOI: 10.1107/S160053680901037X/nc2138sup1.cif

e-65-0o858-sup1.cif^{(30.3KB, cif)}

Structure factors: contains datablocks I. DOI: 10.1107/S160053680901037X/nc2138Isup2.hkl

e-65-0o858-Isup2.hkl^{(412.7KB, 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
N2—H2N⋯O5ⁱ	0.84 (2)	2.23 (2)	2.9383 (17)	143.0 (18)
N4—H4N⋯O1ⁱ	0.875 (19)	2.103 (19)	2.8595 (17)	144.4 (17)
C6—H6⋯O6ⁱⁱ	0.95	2.53	3.339 (2)	143
C16—H16⋯O7ⁱⁱⁱ	0.95	2.38	3.2330 (18)	149
C26—H26C⋯O4^iv	0.98	2.41	3.358 (2)	162
C32—H32⋯O3^v	0.95	2.38	3.2715 (19)	155
C3—H3⋯F1^vi	0.95	2.76	3.308 (2)	118
C29—H29⋯F1^vii	0.95	2.66	3.3715 (19)	133
C13—H13⋯F2^vii	0.95	2.75	3.4627 (19)	133
C19—H19⋯F2^vii	0.95	2.69	3.223 (2)	116

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Symmetry codes: (i) Inline graphic ; (ii) ; (iii) ; (iv) ; (v) ; (vi) ; (vii) .

supplementary crystallographic information

Comment

Immidazolidine-2,4-diones are a valuable class of cyclic urea derivatives exhibiting a broad spectrum of activities ranging from fatty acid amide hydrolase inhibitors (Muccioli et al., 2006) to HIV protease inhibitors (Flosi et al., 2006). Their sulfonyl derivatives not only possess strong inhibitory activity against aldose reductase (Kato, Nakayama, Mizota et al., 1991) but also address diabetic complications such as neuropathy and cataract formation (Kato, Nakayama, Ohta, et al., 1991). Hypoglycemic and aldose reductase inhibitory assay of this novel class of compounds has been reported from this laboratory (Ahmad et al., 2000; Ahmad et al., 2002; Kashif, Ahmad & Hameed, 2008). The crystal structure of 5-(4-Fluorophenyl)-5-methylimidazolidine-2,4-dione (Kashif, Hussain et al., 2008) has been reported previously. The title compound was synthesized by sulfonylation of 5-(4-Fluorophenyl)-5-methylimidazolidine-2,4-dione, to access its hypoglycemic activity.

The title compound crystallizes with two independent molecues (A and B) in the asymmetric unit. It is composed of a methylimidazolidine-2,4-dione moiety substituted with a p-fluorophenyl group and a p-chlorophenylsulfonyl group. Both molecules are U-shaped with a similar geometry and conformation, as can be seen from the Auto-Fit diagram (Fig. 2: Weighted and Unit Weight RMS-Fit = 0.075, 0.069 Å, respectively, for 25 non-H atoms; Spek, 2009). The phenyl ring mean planes are inclined to one another by 6.07 (8)° in molecule A and 8.67 (8)° in molecule B. They are separated with a centroid-to-centroid distance of 3.9096 (10) Å in molecule A, and 3.9118 (10) Å in molecule B. Molecules A and B lie adjacent to one another with a centroid-to-centroid distance of 3.7591 (10) Å between the fluorophenyl ring of molecule A and the chlorophenylsulfonyl ring of molecule B (Fig. 1).

In the crystal structure of the title compound the A and B molecules are linked by N—H···O hydrogen bonds to form a dimer-like arrangement (Fig. 3 and Table 1). These dimers stack along the direction [110] and are linked by C—H···O interactions. The stacks are also linked by C—H···F interactions, and there are some short halide···halide contacts: 3.0499 (14) Å for Cl1···F2ⁱ and 3.1224 (13) Å, for Cl2···F1ⁱ [symmetry operation (i) -x+1, -y, -z+1]) and 3.0612 (17) Å for F1···F2ⁱⁱ [symmetry operation (ii) -x+1, -y+1, -z+1].

Experimental

5-(4-Fluorophenyl)-5-methylimidazolidine-2,4-dione (4.8 mmol) in CH₂Cl₂ (20 ml) as stirred with triethyl amine (4.8 mmol) and catalytic amounts of DMAP. 4-Chlorobenzene sulfonyl chloride (5.8 mmol) in CH₂Cl₂ (10 ml) was added drop wise and the reaction mixture was stirred at rt until complete (controled by TLC). The reaction mixture was diluted with 1 N HCl (20 ml) and extracted with CH₂Cl₂ (3 × 25 ml). The organic layer was dried over anhydrous sodium sulfate and concentrated under reduced pressure. Crystallization of the residue in ethyl acetate afforded the title compound as colourless plate-like crystals, suitable for X-ray analysis.