Molecular structure of 2-nitrobenzenesulphenyl chloride. An electron-diffraction Study

Abstract

From a gas-phase electron-diffraction study an intramolecular non-bonded sulphur–oxygen interaction has been found to be responsible for the planar conformation of 2-nitrobenzenesulphenyl chloride. This investigation reinforces earlier conclusions from crystallographic studies of organosulphur compunds. The S⋯0distance is remarkably short (2.41 Å) and the C1—S⋯O configuration is linear. The following values were obtained for bond lengths (r_a/Å): S—C, 1.776 ± 0.005; S—Cl, 2.046 ± 0.004; N—C, 1.459 ± 0.009; (NO)_mean, 1.229 ± 0.003; (CC)_mean, 1.397 ± 0.003; (C—H)_mean, 1.097 ± 0.010; and bond angles (°) Cl—S—C, 102.3 ± 1.4; S—CC(N), 118.5 ± 1.6; (S)CC—N, 118.5 ± 2.9; C—N0, 119.4 ± 2.8 and 115.5 ± 4.4; NO⋯S, 103.6 ± 2.0; O⋯S—C, 79.9 ± 1.9.