1-(4-Methoxy­phenyl­sulfon­yl)-5-methyl-5-phenyl­imidazolidine-2,4-dione

Abid Hussain; Shahid Hameed; Helen Stoeckli-Evans

doi:10.1107/S1600536809016092

. 2009 May 7;65(Pt 6):o1207–o1208. doi: 10.1107/S1600536809016092

1-(4-Methoxyphenylsulfonyl)-5-methyl-5-phenylimidazolidine-2,4-dione

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

PMCID: PMC2969567 PMID: 21583077

Abstract

The title compound, C₁₇H₁₆N₂O₅S, crystallized in the chiral monoclinic space group P2₁, with two enantiomeric molecules (A and B) in the asymmetric unit. It is composed of a methylimidazolidine-2,4-dione unit substituted with a phenyl group and a 4-methoxyphenylsulfonyl group. The benzene ring mean planes are inclined to one another by 22.20 (14)° in molecule A and by 15.82 (13)° in molecule B. In the crystal structure, the A and B molecules are linked by N—H⋯O hydrogen bonds, forming centrosymmetric dimers. A number of C—H⋯O interactions are also present in the crystal structure, leading to the formation of a three-dimensinoal network.

Related literature

For the applications of immidazolidine-2,4-diones, see: Thenmozhiyal et al. (2004 ▶); Zhang et al. (2004 ▶). For the activity of sulfonylimmidazolidine-2,4-diones, see: Kashif, Ahmad & Hameed (2008 ▶); Ahmad et al. (2000 ▶, 2002 ▶); Murakami et al. (1997 ▶). For related crystal structures, see: Hussain et al. (2009 ▶); Kashif, Hussain et al. (2008 ▶).

Experimental

Crystal data

C₁₇H₁₆N₂O₅S
M _r = 360.38
Monoclinic,
a = 6.2314 (6) Å
b = 17.5694 (12) Å
c = 15.5892 (16) Å
β = 99.373 (12)°
V = 1683.9 (3) Å³
Z = 4
Mo Kα radiation
μ = 0.22 mm⁻¹
T = 173 K
0.38 × 0.30 × 0.19 mm

Data collection

Stoe IPDS diffractometer
Absorption correction: none
13521 measured reflections
6394 independent reflections
4309 reflections with I > 2σ(I)
R _int = 0.033

Refinement

R[F ² > 2σ(F ²)] = 0.029
wR(F ²) = 0.058
S = 0.81
6394 reflections
465 parameters
3 restraints
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.17 e Å⁻³
Δρ_min = −0.20 e Å⁻³
Absolute structure: Flack (1983 ▶), 2987 Friedel pairs
Flack parameter: 0.06 (5)

Data collection: EXPOSE in IPDS-I (Stoe & Cie, 2000 ▶); cell refinement: CELL in IPDS-I; data reduction: INTEGRATE in IPDS-I; 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/S1600536809016092/bt2941sup1.cif

e-65-o1207-sup1.cif^{(31.2KB, cif)}

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809016092/bt2941Isup2.hkl

e-65-o1207-Isup2.hkl^{(312.9KB, 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⋯O8ⁱ	0.91 (2)	1.95 (2)	2.851 (3)	171 (2)
N4—H4N⋯O3ⁱⁱ	0.92 (2)	1.89 (2)	2.800 (3)	171 (2)
C5—H5⋯O2ⁱ	0.95	2.36	3.218 (3)	150
C10—H10A⋯O8	0.98	2.56	3.437 (3)	149
C10—H10B⋯O2	0.98	2.45	3.055 (3)	120
C12—H12⋯O2	0.95	2.52	2.905 (3)	104
C13—H13⋯O9ⁱⁱⁱ	0.95	2.43	3.287 (3)	150
C22—H22⋯O7ⁱⁱ	0.95	2.42	3.351 (3)	165
C24—H24⋯O8^iv	0.95	2.56	3.492 (3)	166
C27—H27A⋯O7	0.98	2.52	3.126 (4)	120
C29—H29⋯O7	0.95	2.54	2.916 (3)	104
C30—H30⋯O4^v	0.95	2.38	3.159 (3)	138
C34—H34⋯O8	0.95	2.56	3.291 (3)	134

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

supplementary crystallographic information

Comment

Imidazolidine-2,4-diones have found applications as androgen receptor antagonists (Zhang et al., 2004) and possess strong anticonvulsant activity (Thenmozhiyal et al., 2004). Sulfonyl derivatives of imidazolidine-2,4-diones on the other hand, are finding utility as inhibitors of aldose reductase (Murakami et al., 1997). The potential of this class of compounds as hypoglycemic agents has already been reported from our laboratory (Kashif, Ahmad & Hameed, 2008; Ahmad et al., 2002, 2000). In continuation of our work on sulfonyl cyclic ureas (Hussain et al., 2009; Kashif, Hussain et al., 2008), the title compound was synthesized taking an imidazolidine-2,4-dione as the scaffold.

The molecular structure of the title compound is illustrated in Fig. 1, and full geometrical details are available in the archived CIF. It crystallized in the chiral monoclinic space group P2₁ with two enantiomeric molecues (A and B) in the asymmetric unit. It is composed of a methylimidazolidine-2,4-dione moiety substituted with a phenyl group and a 4-methoxyphenylsulfonyl group. The bond distances and angles of the two independent molecules are very similar to those observed in 1-(4-Chlorophenylsulfonyl)-5-(4-fluorophenyl)-5-methylimidazolidine-2,4-dione (Hussain et al., 2009), which also crystallized with two independent molecules per asymmetric unit but in the centrosymmetric triclinic space group P-1.

Both molecules A and B are U-shaped with slightly different conformations, as can be seen in the auto-fit view, Fig. 2 (Spek, 2009). The best fit was obtained for inverted molecule B on molecule A (25 non-H atoms) with the weighted and unit weight r.m.s. fits being 0.687 and 0.460 Å, respectively. The benzene ring mean planes are inclined to one another by 22.20 (14) ° in molecule A and 15.82 (13) ° in molecule B. This is different to the situation in the compound mentioned above where the same angles are 6.07 (8) and 8.67 (8) °, for molecules A and B, respectively (Hussain et al., 2009).

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). There are also a number of C—H···O interactions present in the crystal structure, which leads to the formation of a three-dimensional network (Fig. 4 and Table 1).

Experimental

5-Methyl-5-phenylimidazolidine-2,4-dione (4.8 mmol) in CH₂Cl₂ was stirred with triethyl amine (4.8 mmol) and catalytic amounts of DMAP. 4-Methoxybenzene sulfonyl chloride (5.8 mmol) in CH₂Cl₂ was added dropwise. The reaction mixture was stirred continually at 298 K until the reaction was complete (monitored by TLC). The reaction mixture was then diluted with 1 N HCl 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 colourless rod-like crystals of the title compound, suitable for X-ray analysis.