Crystal structure of N-(4-(3-cyclohexyl-5-methyl-2,4-dioxoimidazolidin- 1-ylsulfonyl)phenyl)acetamide, C18H23N3O5S

Abstract

Source of material N-(4-(3-cyclohexyl-5-methyl-2,4-dioxoimidazolidin-1-ylsulfonyl)phenyl) acetamide was prepared by reacting of 2-(4-acetamidophenylsulfonamido)propanoic acid (0.01 mol) and dicyclohexylcarbodiimide (0.01 mol) in dry N,N-dimethylformamide (dmf) over 36 hours at 298 K. After filtration, reduced pressure distillation of dmf, and column chromatography separation, the title compound was obtained. The purified product was dissolved in 95 %ethanol and single crystals were separated after 10 days. Experimental detailsAll Hatoms were positioned geometrically and allowed to ride on their parent atoms at distances of d(Csp 2 -H) =0.93 Å with U iso = 1.2 U eq (parent atom), d(Csp 3 -H) =0 .97 Å with U iso =1 .5 U eq (parent atom) and d(N-H) =0.86 Å with U iso =1.2 U eq (parent atom). DiscussionSulfonamides are among the most widely used antibacterial angents in the world, chiefly because of their low cost, low toxicity, and excellent activity against bacterial diseases. The clinically useful sulfonamides are derived from sulfanilamide, which is similar to para-aminobenzoic acid, afactor required by bacteria for folic acid synthesis [1]. Sulfanilamide was introduced in therapy about half acentury ago for prevention and cure of bacterial infections in humans, and so many derivatives of sulfanilamide have been developed [2][3][4][5]. In the title molecule ( figure, top), the C2-O1 bond lengths (1.205(3).Å)i sl onger than that of standard C=O double bond length 1.170 Å,while the C2-N1 bond distance (1.364(4) Å)is shorter than atypical C-Nbond length (ca. 1.443(4) Å), but longer than atypical double C=N bond (ca. 1.269(2) Å), indicating the electron delocalization at the O1, C2 and N1 atoms [6]. The acetyl-amidocyanogen and the phenyl ring are in the same plane with an r.m.s. deviation of 0.0455 Å (plane p1). The imidazolidine ring and the two oxygen atoms (O4 and O5) are coplanar (r.m.s. deviation =0.0255 Å,plane p2). The dihedral angles formed by p1 and p2 are 81.99(5)°.The unique cyclohexyl group is in achair conformation. Pairs of molecules are linked by intermolecular N1−H1···O5 A (symmetry code A: −x +2,−y,−z+2) hydrogen bond to form ac entrosymmetric hydrogen bonded dimer (figure, bottom) which can be described in graph-set motif of R 2 2 20 () [7].