Syntheses and structures of 1-[2,2-di-chloro-1-hy-droxy-3-(4-methyl-phen-yl)-3-oxoprop-yl]urea and 1-[2,2-di-chloro-3-(4-fluoro-phen-yl)-1-hy-droxy-3-oxoprop-yl]urea.

The title compounds, C(10)H(9)Cl(2)FN(2)O(3), (I), and C(11)H(12)Cl(2)N(2)O(3), (II), are α,α-dihalo-β-diketone urea derivatives, which contain 4-fluoro-phenyl and p-tolyl groups, respectively. The conformation about the C(O)-C(Cl2)-C(O)-N(u) (O = keto, Cl2 = di-chloro, 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).