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Crystal structure of bis-(N-methyl-N-phenyl-amino)-tris-ulfane.

Barany G, Henley MJ, Polski LA, Schroll AL, Young VG - Acta Crystallogr E Crystallogr Commun (2015)

Bottom Line: The core atoms, viz. the N-S-S-S-N moiety, of the two mol-ecules superimpose well if one is inverted on the other, but the phenyl groups do not.In mol-ecule (1 a ), the two phenyl rings are inclined to one another by 86.7 (3)°, and in mol-ecule (1 b ), by 81.1 (3)°.In the crystal, mol-ecules are linked via C-H⋯π inter-actions, forming sheets lying parallel to (010).

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Affiliation: Department of Chemistry, University of Minnesota, Minneapolis, MN 55455, USA.

ABSTRACT
The title compound, C14H16N2S3, crystallized with two independent mol-ecules [(1 a ) and (1 b )] in the asymmetric unit. Both mol-ecules display a pseudo-trans conformation. The two consecutive S-S bond lengths of the tris-ulfane unit of mol-ecule (1 a ) are 2.06 (3) and 2.08 (3) Å, and 2.08 (3) and 2.07 (2) Å for mol-ecule (1 b ). Torsion angles about each of the two S-S bonds are 86.6 (2) and 87.0 (2)° for (1 a ), and -84.6 (2) and -85.9 (2)° for (1 b ). The core atoms, viz. the N-S-S-S-N moiety, of the two mol-ecules superimpose well if one is inverted on the other, but the phenyl groups do not. Thus, the two units are essentially conformational enanti-omers. In mol-ecule (1 a ), the two phenyl rings are inclined to one another by 86.7 (3)°, and in mol-ecule (1 b ), by 81.1 (3)°. In the crystal, mol-ecules are linked via C-H⋯π inter-actions, forming sheets lying parallel to (010).

No MeSH data available.


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The mol­ecular structure of the title compound, showing the atom labelling. Displacement ellipsoids are drawn at the 50% probability level.
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fig1: The mol­ecular structure of the title compound, showing the atom labelling. Displacement ellipsoids are drawn at the 50% probability level.

Mentions: The title compound, (1), was obtained in crystalline form after preparative HPLC, as described by Schroll & Barany (1986 ▸). The proposed mol­ecular structure of (1) was confirmed by single-crystal X-ray analysis at 173 K. The mol­ecules do not take advantage of the twofold axis provided as an available symmetry option by the Fdd2 space group. Instead, there are two mol­ecules, (1a) and (1b), in the asymmetric unit (Fig. 1 ▸), and both of them display a pseudo-trans conformation (see later). All bond distances and angles in both mol­ecules are within expected ranges. Selected geometric parameters for compound (1) are given in Table 1 ▸. The two consecutive S—S bond lengths (comprising the tris­ulfane) of mol­ecule (1a) are 2.064 (3) and 2.078 (3) Å, and for mol­ecule (1b) are 2.076 (3) and 2.067 (2) Å. These values are similar to the value of 2.07 Å reported for the S—S bond length in elemental sulfur (S8). Torsion angles about each of the two S—S bonds (comprising the tris­ulfane) are, respectively, 86.6 (2) and 87.0 (2)° for (1a), and −84.6 (2) and −85.9 (2)° for (1b). The core atoms, viz. the N—S—S—S—N moiety, of the two units superimpose well if one is inverted on the other, but the phenyl groups do not. Thus, the two units are essentially conformational enanti­omers. Moreover, with respect to the four measured torsion angles, which range in absolute value from 84.6 (2) to 87.0 (2)°, these are slightly smaller than the theoretical optimum of 90.0° (Pauling, 1949 ▸; Torrico-Vallejos et al., 2010 ▸). Finally, given the presence of three consecutive linearly connected sulfur atoms, representing two dihedral angles close to 90°, it is noteworthy that both of the mol­ecules in the asymmetric unit display a pseudo-trans conformation (torsion angles +,+ or -,- across the two S—S bonds). The theoretically possible pseudo-cis (torsion angles +,- or -,+) conformation (Meyer, 1976 ▸) was not observed for these structures.


Crystal structure of bis-(N-methyl-N-phenyl-amino)-tris-ulfane.

Barany G, Henley MJ, Polski LA, Schroll AL, Young VG - Acta Crystallogr E Crystallogr Commun (2015)

The mol­ecular structure of the title compound, showing the atom labelling. Displacement ellipsoids are drawn at the 50% probability level.
© Copyright Policy - open-access
Related In: Results  -  Collection

License
Show All Figures
getmorefigures.php?uid=PMC4518933&req=5

fig1: The mol­ecular structure of the title compound, showing the atom labelling. Displacement ellipsoids are drawn at the 50% probability level.
Mentions: The title compound, (1), was obtained in crystalline form after preparative HPLC, as described by Schroll & Barany (1986 ▸). The proposed mol­ecular structure of (1) was confirmed by single-crystal X-ray analysis at 173 K. The mol­ecules do not take advantage of the twofold axis provided as an available symmetry option by the Fdd2 space group. Instead, there are two mol­ecules, (1a) and (1b), in the asymmetric unit (Fig. 1 ▸), and both of them display a pseudo-trans conformation (see later). All bond distances and angles in both mol­ecules are within expected ranges. Selected geometric parameters for compound (1) are given in Table 1 ▸. The two consecutive S—S bond lengths (comprising the tris­ulfane) of mol­ecule (1a) are 2.064 (3) and 2.078 (3) Å, and for mol­ecule (1b) are 2.076 (3) and 2.067 (2) Å. These values are similar to the value of 2.07 Å reported for the S—S bond length in elemental sulfur (S8). Torsion angles about each of the two S—S bonds (comprising the tris­ulfane) are, respectively, 86.6 (2) and 87.0 (2)° for (1a), and −84.6 (2) and −85.9 (2)° for (1b). The core atoms, viz. the N—S—S—S—N moiety, of the two units superimpose well if one is inverted on the other, but the phenyl groups do not. Thus, the two units are essentially conformational enanti­omers. Moreover, with respect to the four measured torsion angles, which range in absolute value from 84.6 (2) to 87.0 (2)°, these are slightly smaller than the theoretical optimum of 90.0° (Pauling, 1949 ▸; Torrico-Vallejos et al., 2010 ▸). Finally, given the presence of three consecutive linearly connected sulfur atoms, representing two dihedral angles close to 90°, it is noteworthy that both of the mol­ecules in the asymmetric unit display a pseudo-trans conformation (torsion angles +,+ or -,- across the two S—S bonds). The theoretically possible pseudo-cis (torsion angles +,- or -,+) conformation (Meyer, 1976 ▸) was not observed for these structures.

Bottom Line: The core atoms, viz. the N-S-S-S-N moiety, of the two mol-ecules superimpose well if one is inverted on the other, but the phenyl groups do not.In mol-ecule (1 a ), the two phenyl rings are inclined to one another by 86.7 (3)°, and in mol-ecule (1 b ), by 81.1 (3)°.In the crystal, mol-ecules are linked via C-H⋯π inter-actions, forming sheets lying parallel to (010).

View Article: PubMed Central - HTML - PubMed

Affiliation: Department of Chemistry, University of Minnesota, Minneapolis, MN 55455, USA.

ABSTRACT
The title compound, C14H16N2S3, crystallized with two independent mol-ecules [(1 a ) and (1 b )] in the asymmetric unit. Both mol-ecules display a pseudo-trans conformation. The two consecutive S-S bond lengths of the tris-ulfane unit of mol-ecule (1 a ) are 2.06 (3) and 2.08 (3) Å, and 2.08 (3) and 2.07 (2) Å for mol-ecule (1 b ). Torsion angles about each of the two S-S bonds are 86.6 (2) and 87.0 (2)° for (1 a ), and -84.6 (2) and -85.9 (2)° for (1 b ). The core atoms, viz. the N-S-S-S-N moiety, of the two mol-ecules superimpose well if one is inverted on the other, but the phenyl groups do not. Thus, the two units are essentially conformational enanti-omers. In mol-ecule (1 a ), the two phenyl rings are inclined to one another by 86.7 (3)°, and in mol-ecule (1 b ), by 81.1 (3)°. In the crystal, mol-ecules are linked via C-H⋯π inter-actions, forming sheets lying parallel to (010).

No MeSH data available.


Related in: MedlinePlus