Polysulfonylamine, LXXVI [1] Zwei supramolekulare Isomere im gleichen Kristall: Darstellung und Struktur des monomeren 18-Krone-6-Komplexes (CH₂CH₂O)₆·2 MeN(SO₂Me)(SO₂Ph) / Polysulfonylamines, LXXVI [1] Occurrence of Two Supramolecular Isomers in One Crystal: Synthesis and Structure of the Monomeric 18-Crown-6 Complex (CH₂CH₂O)₆ • 2 MeN(SO₂Me) (SO₂Ph)

Abstract

The title complex, obtained by co-crystallization of its molecular components from methanol, was characterized by low-temperature X-ray diffraction. The crystal structure (triclinic, space group P1̄, Z = 2) consists of two monomeric and crystallographically centrosymmetric formula units A and B which may be classified as supramolecular stereo- and/or linkage isomers. In both units, the receptor rings adopt the frequently observed D3d pseudosymmetry, and the symmetry-related substrate molecules are situated above and below the polyether rings. The isomerism of the supermolecules arises from markedly different confomations of their substrate components. In B, the methyl groups display a transoid orientation (torsional angle for C - N - S - C : 135.5°) and the N-methyldisulfonylamine is solely attached by three S - C - H ··· O interactions to a set of three alternating crown oxygen atoms. In isomer A, the C -N - S - Cmethyl sequence is cisoid (torsional angle: 83.1°) and the substrate is connected to the crown ether by three S - C - H ··· O bonds and an additional N - C - H ··· O interaction. The H ··· O distances and C -H ··· O angles of the seven independent hydrogen bonds lie within the intervals 230-260 pm and 140-180°, respectively. A supermolecule involving MeN (SO2Ph)2 and 18-crown-6 could not be isolated, whereas the binary complex (CH2CH2O)6•2 MeN(SO2F)2 is readily obtained by co-crystallization of the components. The latter complex showed severe disorder of the N(SO2F)2 moieties and its structure could not be refined satisfactorily.

N-Methyl-N-methylsulfonyl-2-nitrobenzenesulfonamide

“…In the title compound ( Fig. 1), all bond lengths and angles are normal (Allen et al, 1987) and in good agreement with those reported previously for similar molecules (Henschel et al, 1996). The molecular structure is stabilized by intramolecular C-H•••O hydrogen bonds involving the oxygen atoms bound to atom S1 (Table 1).…”

“…For literature on the biological activities of sulfonimide compounds, see: Kamoshita et al (1987). For the crystal structure of related compounds, see: Henschel et al (1996). For related literature, see: Allen et al (1987); Zhang et al (2007).…”

2-[(E)-(Dimethylamino)methyleneamino]-N-phenylbenzenesulfonamide

“…For a related crystal structure, see: Henschel et al (1996). For applications of sulfonimide derivatives, see: Kamoshita et al (1987) and Zhang et al (2007).…”

N-[(4-Methylphenyl)sulfonyl]acetamide

“…In addition, the nature and position of substituents play a significant role on the crystal structures of N-(aryl)-amides and N-(aryl)-sulfonamides (Gowda et al, 2007(Gowda et al, , 2010Shakuntala et al, 2011a,b;Henschel et al, 1996). In view of the importance of the biological activities of sulfonamide containing compounds, we report herein the crystal structure of the title compound.…”

“…For related structures, see : Henschel et al (1996); Gowda et al (2007Gowda et al ( , 2010 ;Shakuntala et al (2011a,b). For the stability of the temperature controller used in the data collection, see : Cosier & Glazer (1986).…”