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The conformational features of three 2-sulphur-substituted cyclohexanone derivatives, which differ in the number of sulphur-bound oxygen atoms,  i.e.  zero ( I ), one ( II ) and two ( III ), were investigated by single crystal X-ray crystallography and geometry optimized structures determined using Hartree-Fock method. In each of ( I )–( III ) an intramolecular S … O carbonyl  interaction is found with the magnitude correlated with the oxidation state of the sulphur atom,  i.e . 2.838(3) Å in ( I ) to 2.924(2) Å in ( II ) to 3.0973(18) Å in ( III ). There is an inverse relationship between the strength of this interaction and the magnitude of the carbonyl bond. The supramolecular aggregation patterns are primarily determined by C–H … O contacts and are similarly influenced by the number of oxygen atoms in the molecular structures. Thus, a supramolecular chain is found in the crystal structure of ( I ). With an additional oxygen atom available to participate in C–H … O interactions, as in ( II ), a two-dimensional array is found. Finally, a three-dimensional network is found for ( III ). Despite there being differences in conformations between the experimental structures and those calculated in the gas-phase, the S … O interactions persist. The presence of intermolecular C–H … O interactions involving the cyclohexanone-carbonyl group in the solid-state, disrupts the stabilising intramolecular C–H … O interaction in the energetically-favoured conformation. ( I ): C 12 H 13 NO 3 S, triclinic space group  P -1 with  a  = 5.392(3) Å,  b  = 10.731(6) Å,  c  = 11.075(6) Å,  α  = 113.424(4)°,  β  = 94.167(9)°,  γ  = 98.444(6)°,  V  = 575.5(6) Å 3 ,  Z  = 2,  R  1  = 0.052; ( II ): C 12 H 13 NO 4 S, monoclinic  P 2 1 / n ,  a  = 7.3506(15) Å,  b  = 6.7814(14) Å,  c  = 23.479(5) Å,  β  = 92.94(3)°,  V  = 1168.8(4) Å 3 ,  Z  = 4,  R  1  = 0.046; ( III ): C 12 H 13 NO 5 S, monoclinic  P 2 1 / c ,  a  = 5.5491(11) Å,  b  = 24.146(3) Å,  c  = 11.124(3) Å,  β  = 114.590(10)°,  V  = 1355.3(5) Å 3 ,  Z  = 4,  R  1  = 0.051.

zeitschrift für kristallographie

Crystal and molecular structures of three 2-sulphur-substituted cyclohexanones studied by X-ray crystallography and by  ab initio  molecular orbital calculations