Syntheses and structures of 1-[2,2-di­chloro-1-hy­droxy-3-(4-methyl­phen­yl)-3-oxoprop­yl]urea and 1-[2,2-di­chloro-3-(4-fluoro­phen­yl)-1-hy­droxy-3-oxoprop­yl]urea

Abstract

The title compounds, C₁₀H₉Cl₂FN₂O₃, (I), and C₁₁H₁₂Cl₂N₂O₃, (II), are α,α-dihalo-β-diketone urea derivatives, which contain 4-fluoro­phenyl and p-tolyl groups, respectively. The conformation about the C_O—C_Cl2—C_O—N_u (O = keto, Cl2 = di­chloro, u = urea) bond is anti in (I) and gauche in (II). In the crystals of both compounds, O—H⋯O hydrogen bonds generate inversion dimers and the dimers are linked into (100) layers by N—H⋯O hydrogen bonds.

The title compounds, C₁₀H₉Cl₂FN₂O₃, (I), and C₁₁H₁₂Cl₂N₂O₃, (II), are α,α-dihalo-β-diketone urea derivatives, which contain 4-fluoro­phenyl and p-tolyl groups, respectively. The conformation about the C_O—C_Cl2—C_O—N_u (O = keto, Cl2 = di­chloro, u = urea) bond is anti in (I) and gauche in (II). In the crystals of both compounds, O—H⋯O hydrogen bonds generate inversion dimers and the dimers are linked into (100) layers by N—H⋯O hydrogen bonds. The Hirshfeld surface analyses of the crystal structures indicate that the most important contributions for the crystal packings are from H⋯O/O⋯H (22.3%), H⋯H (20.9%), H⋯Cl/Cl⋯H (15.6%) and H⋯C/C⋯H (10.3%) for (I) and H⋯H (31.7%), H⋯O/O⋯H (25.1%), H⋯Cl/Cl⋯H (21.1%) and H⋯C/C⋯H (9.5%) for (II).