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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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Compounds that also have an N—S—S—S—N moiety, viz. bis­(oxamido)­tris­ulfane, (2) (CSD refcode, GEHPUE; Brunn et al., 1988 ▸), and bis­[tert-but­yl(di-tert-butyl­fluoro­sil­yl)amino]­tris­ulfane, (3) (SOTLAO; Klingebiel et al., 1991 ▸).
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fig3: Compounds that also have an N—S—S—S—N moiety, viz. bis­(oxamido)­tris­ulfane, (2) (CSD refcode, GEHPUE; Brunn et al., 1988 ▸), and bis­[tert-but­yl(di-tert-butyl­fluoro­sil­yl)amino]­tris­ulfane, (3) (SOTLAO; Klingebiel et al., 1991 ▸).

Mentions: A search of the Cambridge Structural Database (CSD, Version 5.36, February 2015; Groom & Allen, 2014 ▸) revealed the presence of two compounds (see Fig. 3 ▸) that also have an N—S—S—S—N moiety, viz. bis­(oxamido)­tris­ulfane, (2) (CSD refcode GEHPUE; Brunn et al., 1988 ▸), and bis­[tert-but­yl(di-tert-butyl­fluoro­sil­yl)amino]­tris­ulfane, (3) (SOTLAO; Klingebiel et al., 1991 ▸). Unlike the title compound, (1), compounds (2) and (3) each have a unique conformation in the unit cell (Z′ = 1). Selected geometric parameters of (1) and the comparison compounds, (2) and (3), are given in Table 1 ▸. While the average S—S bond length of the title compound is ca 2.07 Å, the corresponding value is longer (2.09 Å) in (3) and shorter (2.04 Å) in (2). The absolute value of the average torsion angle of the title compound (1) is ca 86.0°, while the corresponding value is larger (93.2 and −89.5°) and closer to the theoretical optimum in (2), and significantly larger (109.7 and 95.9°) in (3).


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)

Compounds that also have an N—S—S—S—N moiety, viz. bis­(oxamido)­tris­ulfane, (2) (CSD refcode, GEHPUE; Brunn et al., 1988 ▸), and bis­[tert-but­yl(di-tert-butyl­fluoro­sil­yl)amino]­tris­ulfane, (3) (SOTLAO; Klingebiel et al., 1991 ▸).
© Copyright Policy - open-access
Related In: Results  -  Collection

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

fig3: Compounds that also have an N—S—S—S—N moiety, viz. bis­(oxamido)­tris­ulfane, (2) (CSD refcode, GEHPUE; Brunn et al., 1988 ▸), and bis­[tert-but­yl(di-tert-butyl­fluoro­sil­yl)amino]­tris­ulfane, (3) (SOTLAO; Klingebiel et al., 1991 ▸).
Mentions: A search of the Cambridge Structural Database (CSD, Version 5.36, February 2015; Groom & Allen, 2014 ▸) revealed the presence of two compounds (see Fig. 3 ▸) that also have an N—S—S—S—N moiety, viz. bis­(oxamido)­tris­ulfane, (2) (CSD refcode GEHPUE; Brunn et al., 1988 ▸), and bis­[tert-but­yl(di-tert-butyl­fluoro­sil­yl)amino]­tris­ulfane, (3) (SOTLAO; Klingebiel et al., 1991 ▸). Unlike the title compound, (1), compounds (2) and (3) each have a unique conformation in the unit cell (Z′ = 1). Selected geometric parameters of (1) and the comparison compounds, (2) and (3), are given in Table 1 ▸. While the average S—S bond length of the title compound is ca 2.07 Å, the corresponding value is longer (2.09 Å) in (3) and shorter (2.04 Å) in (2). The absolute value of the average torsion angle of the title compound (1) is ca 86.0°, while the corresponding value is larger (93.2 and −89.5°) and closer to the theoretical optimum in (2), and significantly larger (109.7 and 95.9°) in (3).

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