The Crystal and Molecular Structure of endo-3-Benzylsulfinylbicyclo[2.2.1]heptane-endo-2-carboxylic Acid.

(2-Oxo-1,3-thiazolidin-3-yl)carbonylthioethylammonium Nitrate, C6H11N2O2S2+.NO3−

“…Among the intramolecular distances it is significant that the S(2)..-O(1) distance [2.734 (3) /~] is shorter than the sum of the van der Waals radii for these atoms (3.5/~) (Abrahamsson & Zacharis, 1976). Clearly the electronic interaction between the negatively polarized carbonyl O atom and the positively charged endocyclic S atom is sufficiently strong at this distance to compensate for the repulsive forces between these atoms.…”

Structure of 2-benzoylimino-3-methyl-1,3-thiazolidine: a comparison of intramolecular X–S...O = Y interactions

“…As shown by the puckering parameters (Cremer & Pople, 1975) and asymmetry parameters (Duax, Weeks & Rohrer, 1976) O tp ACsIC (2) (Table 5) reveal a distorted mirror symmetry between (a) and (b). In each molecule the phenyl group lies approximately in the plane (Table 6) Abrahamsson & Zacharis (1976) the interaction between the negatively polarized carbonyl O atom with the positively charged S is strong enough even at a distance of 2.8 ,~ to compensate the repulsion forces between S and O. Contrary to this Beer, McMonagle, Siddiqui, Hordvik & Jynge (1979), in accord with the conclusion of Adman, Jensen & Warrener (1975), claim that in the range 2.6-2.8 ,~ there is very little or no bonding between S and O atoms.…”

Directly Linked C-Disaccharides: Structures of Two 3,4-Dihydro-2H-pyran Derivatives

“…In both cases, the substituents are oriented such that S or 08 lies on the same side of the C3--C4 bond as O1 (Z configuration) and therefore trans to the C4==C5 double bond, with the vicinal 1,4 intramolecular contacts [S...O1 -2.854(2) and O8...O1 -2.699 (3) ,~,] being shorter than the sum of van der Waals radii (S..-O = 3.24, O...O = 3.00A; Bondi, 1964). While it has been known for a long time that sulfur can approach other atoms at 'non-bonded' distances much shorter than the sum of the van der Waals radii (Donohue, 1950;Nardelli, Braibanti & Fava, 1957;Lozac'h, 1971;Abrahamsson, Rehenberg, Liljefors & Sandstrom, 1974;Abrahamsson & Zacharis, 1976), the same cannot be said about the O...O contacts, but a search in the Cambridge Structural Database (Allen et al, 1991) shows that the contact present in (4) falls in the most populated range of values (2.68-2.72 A) for this kind of non-bonded contact.…”