Selective inclusion crystallization of phenol derivatives with tetraalkylammonium salts

The structures of four inclusion compounds of alkylammonium bromides with phenol derivatives are reported. Crystal data: (1) H1c. G4, monoclinic, P21/m with a = 5.5388(4), b = 7.4464(9), c = 32.421(5) Å, β = 92.43°, Z = 2, DC = 1.24 g cm−3, R = 0.082 for 1556 observed reflections. (2) H1c. G2b, monoclinic, P21/m with a = 11.154(2), b = 7.470(1), c = 31.767(5) Å, β = 91.42°, Z = 2, DC = 1.13 g cm−3, R = 0.061 for 2710 observed reflections. (3) H2b.G1, orthorhombic, Pbca with a = 15.215(3), b = 16.208(1), c = 19.827(5) Å, Z = 8, DC = 1.13 g cm−3, R = 0.061 for 1613 observed reflections. (4) H3.G6, monoclinic, P21/c with a = 9.472(2), b = 18.345(2), c = 16.384(3) Å, β = 105.73°, Z = 4, DC = 1.20 g cm−3, R = 0.050 for 1783 observed reflections. The molecules are held in their aggregates by O…Br hydrogen bonding. The inclusion compounds can also be formed in the solid state by shaking together the powdered components. The reaction was followed by UV spectroscopy. Isomeric separation of the phenol derivatives was carried out using inclusion crystallization. The phenols were obtained in high purities in yields ranging from 20 to 60%.