New 1,3,5-dithiazinanes bearing β-alcohol or β-sulphonates chains at C2. Non classical S→phenyl and S→C interactions

The synthesis of six new 1,3,5-dithiazinanes bearing functionalised alkyl chains at carbon-2 are reported: 1-(5-methyl-1,3,5-dithiazinan-2-yl)propan-2-ol ( 5 ), 1-(5-methyl-1,3,5-dithiazinan-2-yl)-3-phenoxypropan-2-ol ( 6 ), ( R ) 2-(5-methyl-1,3,5-dithiazinan-2-yl)-1-phenylethan-1-ol ( 7 ), 1-(5-methyl-1,3,5-dithiazinan-2-yl)propan-2-yl-4-methylbenzene-sulphonate ( 8 ), 1-(5-methyl-1,3,5-dithiazinan-2-yl)-3-phenoxypropan-2-yl-4-methyl benzene-sulphonate ( 9 ) and 1-(5-methyl-1,3,5-dithiazinan-2-yl)propan-2-yl-methane sulphonate ( 10 ). X-Ray diffraction analysis of compounds 7 and 8 are discussed. In the crystal of compound 8 a non-classical S(lp)→phenyl (π-hole) intramolecular interaction was observed. In the crystal net of compound 8, dimers formed by two cooperative contacts between the S1 of one molecule and a methyl σ-hole of a second molecule were analysed. The weak interactions observed in the crystal of compound 8 were confirmed by calculations. The most stable conformers of molecules 6, 8 - 10, calculated in the gas phase, are reported as well as NBO charges, molecular graphs and reduced gradient maps of the electronic density.