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The title thia-pyrazino-phanes, 2,5,8,11,14,17-hexa-thia-[9.9](2,6,3,5)-pyrazino-phane, C 16 H 24 N 2 S 6 , ( I ), and 2,5,8,11,14,17-hexa-thia-[9.9](2,5,3,6)-pyrazino-phane, C 16 H 24 N 2 S 6 , ( II ), are regioisomers; m -bis L1 and p -bis L1, respectively. Both compounds have a central tetra-2,3,5,6-methyl-ene-pyrazine unit with two -S-CH 2 -CH 2 -S-CH 2 -CH 2 -S- chains, linking the methyl-ene C atoms at positions 2 and 6 and 3 and 5 on the pyrazine ring of I , but linking the methyl-ene C atoms at positions 2 and 5 and 3 and 6 on the pyrazine ring of II . Both compounds crystallize with half a mol-ecule in the asymmetric unit. The whole mol-ecule of I is generated by inversion symmetry, with the pyrazine ring being located about a center of symmetry. The whole mol-ecule of II is generated by twofold rotation symmetry, with the pyrazine N atoms being located on the twofold rotation axis. In compound I , there are pairs of intra-molecular C-H⋯S contacts present, but none in compound II . In the crystal of I , there are no significant inter-molecular inter-actions present, while in the crystal of II , mol-ecules are linked by pairs of C-H⋯S hydrogen bonds, forming corrugated layers lying parallel the ac plane. The Hirshfeld surfaces and the energy frameworks of the two regioisomers indicate little difference in the inter-atomic contacts, which are dominated by dispersion forces.

acta crystallographica. section e, crystallographic communications

The crystal structures, Hirshfeld surface analyses and energy frameworks of two hexathiapyrazinophane regioisomers; 2,5,8,11,14,17-hexathia-[9.9](2,6,3,5)-pyrazinophane and 2,5,8,11,14,17-hexathia-[9.9](2,5,3,6)-pyrazinophane