Crystal structures of the 2:2 complex of 1,1'-(1,2-phenyl-ene)bis-(3-m-tolyl-urea) and tetra-butyl-ammonium chloride or bromide.

The title compounds, tetra-butyl-ammonium chloride-1,1'-(1,2-phenyl-ene)bis-(3-m-tolyl-urea) (1/1), C16H36N(+)·Cl(-)·C22H22N4O2 or [(n-Bu4N(+)·Cl(-))(C22H22N4O2)] (I) and tetra-butyl-ammonium bromide-1,1'-(1,2-phenyl-ene)bis-(3-m-tolyl-urea) (1/1), C16H36N(+)·Br(-)·C22H22N4O2 or [(n-Bu4N(+)·Br(-))(C22H22N4O2)] (II), both comprise a tetra-butyl-ammonium cation, a halide anion and an ortho-phenyl-ene bis-urea mol-ecule. Each halide ion shows four N-H⋯X (X = Cl or Br) inter-actions with two urea receptor sites of different bis-urea moieties. A crystallographic inversion centre leads to the formation of a 2:2 arrangement of two halide anions and two bis-urea mol-ecules. In the crystals, the dihedral angle between the two urea groups of the bis-urea mol-ecule in (I) [defined by the four N atoms, 165.4 (2)°] is slightly smaller than that in (II) [167.4 (2)°], which is probably due to the smaller ionic radius of chloride compared to bromide.