Abstract
The crystal structure of 1,3-di-thiane 1,1,3,3-tetra-oxide, C4H8O4S2, has been determined to examine the inter-molecular C-H⋯O hydrogen bonds in a small mol-ecule with highly polarized hydrogen atoms. The crystals are monoclinic, space group Pn, with a = 4.9472 (5), b = 9.9021 (10), c = 7.1002 (7) Å and β = 91.464 (3)° with Z = 2. The mol-ecules form two stacks parallel to the a axis with the molecules being one a translation distance from each other. This stacking involves axial hydrogen atoms on one mol-ecule and the axial oxygen atoms on the adjacent mol-ecule in the stack. None of these C-H⋯O contacts is particularly short (all are > 2.4 Å). The many C-H⋯O contacts between the two stacks involve at least one equatorial hydrogen or oxygen atom. Again, no unusually short contacts are found. The whole crystal structure basically consists of a complex network of C-H⋯O contacts with no single, linear C-H⋯O contacts, only contacts that involve two (bifurcated), and mostly three or four neighbors.
Highlights
The crystal structure of 1,3-dithiane 1,1,3,3-tetraoxide, C4H8O4S2, has been determined to examine the intermolecular C—HÁ Á ÁO hydrogen bonds in a small molecule with highly polarized hydrogen atoms
The whole crystal structure basically consists of a complex network of C—HÁ Á ÁO contacts with no single, linear C—HÁ Á ÁO contacts, only contacts that involve two, and mostly three or four neighbors
This is the second in a series looking at the C—HÁ Á ÁO contacts in cyclic organic structures containing multiple sulfone groups [see Harlow et al (2019) for the first structure in the series: 1,4dithiane 1,1,4,4-tetraoxide]
Summary
This is the second in a series looking at the C—HÁ Á ÁO contacts in cyclic organic structures containing multiple sulfone groups [see Harlow et al (2019) for the first structure in the series: 1,4dithiane 1,1,4,4-tetraoxide]. Any methylene group adjacent to a sulfone has polarized hydrogen atoms. Methylene groups bonded to two sulfones are polarized to such an extent that they may form a C—HÁ Á ÁX (X = N, O) hydrogen bond (Harlow et al, 1984) as illustrated. The structure of the unsubstituted 1,3-disulfone, has not been previously reported and was of interest because of its high melting point (583 K) and decomposition temperatures (ca 623 K), which are suggestive of potentially strong C—HÁ Á ÁO contacts. E77, 204–207 for further details of 1H NMR spectra and hydrogen-atom polarity in disulfones
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