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

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.

The title compound, C 17 H 16 N 2 O 5 S, crystallized in the chiral monoclinic space group P2 1 , 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-HÁ Á ÁO hydrogen bonds, forming centrosymmetric dimers. A number of C-HÁ Á ÁO interactions are also present in the crystal structure, leading to the formation of a three-dimensinoal network.
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 P2 1 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 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 CH 2 Cl 2 was stirred with triethyl amine (4.8 mmol) and catalytic amounts of DMAP. 4-Methoxybenzene sulfonyl chloride (5.8 mmol) in CH 2 Cl 2 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 CH 2 Cl 2 (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.

Refinement
The NH H-atoms were located in difference Fourier maps and freely refined. The H-atoms bonded to C were included in calculated positions [C-H = 0.95 -0.98 Å] and treated as riding with U iso (H) = 1.2U eq (C) or 1.5U eq (C methyl ). Fig. 1. A view of the molecular structure of the two indepenent molecules of the title compound. Displacement ellipsoids are drawn at the 50% probabiltiy level.   Table 1 for details). Fig. 4. A perspective view along the a axis of the crystal packing in the title compound showing the N-H···O and C-H···O hydrogen bonds, which link the molecules to form a three-dimensional network (see Table 1 for details).