Xiao-Qing Cai, Xiao-Nuan Xie, Xiaowei Yan
2009
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Zeitschrift für Kristallographie - New Crystal Structures
Abstract
C18H23N3O5S, triclinic, P1 (no. 2), a = 6.655(1) Å, b = 10.874(2) Å, c = 13.787(2) Å, 0 = 76.321(4)°, . = 87.388(4)°, = 80.611(3)°, V = 956.4 Å, Z = 2, Rgt(F) = 0.053, wRref(F) = 0.137, T = 298 K. Source of material N-(4-(3-cyclohexyl-5-methyl-2,4-dioxoimidazolidin-1-ylsulfonyl)phenyl) acetamide was prepared by reacting of 2-(4acetamidophenylsulfonamido)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 details All H atoms were positioned geometrically and allowed to ride on their parent atoms at distances of d(Csp—H) = 0.93 Å with Uiso = 1.2 Ueq(parent atom), d(Csp—H) = 0.97 Å with Uiso = 1.5 Ueq(parent atom) and d(N—H) = 0.86 Å with Uiso = 1.2 Ueq(parent atom). Discussion Sulfonamides 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, a factor required by bacteria for folic acid synthesis [1]. Sulfanilamide was introduced in therapy about half a century ago for prevention and cure of bacterial infections in humans, and so many derivatives of sulfanilamide have been developed [2-5]. In the title molecule (figure, top), the C2—O1 bond lengths (1.205(3).Å) is longer 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 a typical C—N bond length (ca. 1.443(4) Å), but longer than a typical 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 a chair conformation. Pairs of molecules are linked by intermolecular N1−H1···O5 (symmetry code A: −x +2,−y,−z+2) hydrogen bond to form a centrosymmetric hydrogen bonded dimer (figure, bottom) which can be described in graph-set motif of R2 2 20 ( ) [7]. Z. Kristallogr. NCS 224 (2009) 213-214 / DOI 10.1524/ncrs.2009.0095 213 © by Oldenbourg Wissenschaftsverlag, München Crystal: colorless block, size 0.20 × 0.27 × 0.29 mm Wavelength: Mo K0 radiation (0.71073 Å) &: 2.04 cm−1 Diffractometer, scan mode: Bruker APEX CCD, +/1 2"max: 50.04° N(hkl)measured, N(hkl)unique: 5001, 3305 Criterion for Iobs, N(hkl)gt: Iobs > 2 !(Iobs), 2602 N(param)refined: 246 Programs: SHELXS-97 [8], SHELDXL-97 [9], SHELXTL [10] Table 1. Data collection and handling.