Abstract
Abstract X-Ray analysis of N,N'-dibenzyl-N-(5,5-dimethyl-2-oxo-1,3,2 -dioxaphosphoranyl)-thiourea (1) and its dicyclohexyl analog (2) revealed important structural differences in the solid state. The thiourea moiety in 1 formed by the atoms S, C(1), N(1) and N(2) has been found to be planar. The sulphur and phosphorus atoms in 1 adopt a practically antiperiplanar arrangement around the C(1)[sbnd]N(1) bond (the torsional angle 159.0(3)°). The molecule of 1 is stabilized by an intramolecular N[sbnd]H … O[dbnd]P hydrogen bond. In contrast to 1, compound 2 has a non-planar thiourea skeleton and the sulphur and phosphorus atoms are close to each other (the torsional angle P[sbnd]N(1)[sbnd]C(1)[sbnd]S is 91(1)° and the non-bonding S ° P distance is equal to 3.73 A). The molecules of 2 form dimeric structures due to intermolecular hydrogen bonds between the NH-protons and PO-groups.
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