Bisphenol flukicides. VI. The crystal and molecular structures of 2,2'-(Phenoxymethylene)bis(4-chloro-6-nitrophenol) and a triethylamine adduct of 2,2'-(Benzyloxymethylene)bis(4-chloro-6-nitrophenol)

Abstract

X-ray crystallographic analyses have defined the conformational detail in the title compounds. Crystals of 2,2'-(phenoxymethylene)bis(4-chloro-6-nitrophenol) (1), C_l9H₁₂Cl₂N₂O₇, are monoclinic: space group P2₁/n, a 8.616(1), b 16.214(1), c l3.727(1) Å, β 92.13(1)º and Z 4. The triethylamine adduct of 2,2'-(benzyloxymethylene)bis(4-chloro-6-nitrophenol) (2),Et₃N, C₂₀H₁₄Cl₂N₂O₇,C₆H₁₅N, crystallizes in the monoclinic space group P2₁/c with a 9.454(1), b 11.911(2), c 25.392(2) Å, ββ 109.96(1)º and Z 4. The structures were refined with diffractometer data measured with Cu Kα radiation to R 0.061 (1761 terms) for (1) and R 0.063 (1230 terms) for (2),Et₃N. The methylenebisphenol moieties in the molecules of (1) and (2) adopt twist and butterfly conformations respectively. In (1), the dihedral angles between the perpendiculars to the plane of the C-C-C bridge and the phenol rings are 61.1(4) and 71.6(4)º; in (2), these angles have values of 88.0(8) and 85.6(7)º.