Synthesis and Structural Characterization of Cyclohexanaminium 2-(Methoxycarbonyl)-3,4,5,6-Tetrabromobenzoate Methanol Solvate

Abstract

The title compound cyclohexanaminium 2-(methoxycarbonyl)-3,4,5,6-tetrabromo benzoate methanol solvate (C16H21Br4NO5, Mr = 626.94) was synthesized and characterized by single crystal X-ray diffraction. The crystal belongs to monoclinic, space group P21/c, with a = 18.4464(16), b = 13.4490(14), c = 8.8614(7) A, β = 90.5550(10) °, V = 2198.3(3) A3, Z = 4, Dc = 1.894 g/cm3, λ = 0.71073 A, μ (MoK α ) = 7.347 mm-1, F(000) = 1216. The final refinement gave R = 0.0430, wR(F2) = 0.0743 for 10,893 observed reflections with I > 2(I). X-ray diffraction analysis reveals that in the title compound, C6H14N+ · C9H3Br4O4 - · CH4O, the N atoms of the cyclohexanamine molecule are protonated. In the anion, the mean planes of the methoxycarbonyl and carboxylate groups form dihedral angles of 71.7 (3) and 94.7 (3) °, respectively with the benzene ring. The crystal structure is stabilized by N---H...O hydrogen bonds between cyclohexanaminium and 2-(methoxycarbonyl)- 3,4,5,6-tetrabromobenzoate anion, and by O---H...O and N---H...O hydrogen bonds between methanol, 2-(methoxycarbonyl)-3,4,5,6-tetrabromobenzoate and cyclohexanaminium.