3,3′-Dibenzoyl-1,1′-dibenzyl-1,1′-(ethane-1,2-diyl)dithiourea

Andrzej Okuniewski,Jaroslaw Chojnacki,Barbara Becker

doi:10.1107/s1600536812002954

Andrzej Okuniewski, Jaroslaw Chojnacki + Show 1 more

Open Access

https://doi.org/10.1107/s1600536812002954

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Abstract

In the title compound, C32H30N4O2S2, the carbonyl and thiocarbonyl groups are found in a rare synclinal conformation, with an S—C⋯C—O pseudo-torsion angle of 62.6 (2)°. The molecule has Ci = S 2 point-group symmetry with a crystallographic center of inversion located in the middle of the ethylene bridge. One of the symmetry-independent phenyl rings is disordered over two orientations, with a site-occupation ratio of 70:30. The distances between the centroids of the nearest phenyl rings are equal to one of the lattice constants [a = 4.7767 (2) Å], so stacking interactions are extremely weak. Molecules are joined by bifurcated hydrogen bonds (N—H⋯O and N—H⋯S), forming a ladder-like arrangement along [100]. van der Waals forces combine these ladders into a three-dimensional structure. The dependency between the S⋯O distance and the improper S=C⋯C=O torsion angle based on 739 structures containing the CC(=O)NC(=S)N moiety is discussed.

Highlights

C32H30N4O2S2, the carbonyl and thiocarbonyl groups are found in a rare synclinal conformation, with an S—C C—O pseudo-torsion angle of 62.6 (2)
The molecule has Ci = S2 point-group symmetry with a crystallographic center of inversion located in the middle of the ethylene bridge
One of the symmetry-independent phenyl rings is disordered over two orientations, with a siteoccupation ratio of 70:30

Summary

Structure Reports

C32H30N4O2S2, the carbonyl and thiocarbonyl groups are found in a rare synclinal conformation, with an S—C C—O pseudo-torsion angle of 62.6 (2). The molecule has Ci = S2 point-group symmetry with a crystallographic center of inversion located in the middle of the ethylene bridge. One of the symmetry-independent phenyl rings is disordered over two orientations, with a siteoccupation ratio of 70:30. The distances between the centroids of the nearest phenyl rings are equal to one of the lattice constants [a = 4.7767 (2) Å], so stacking interactions are extremely weak. Van der Waals forces combine these ladders into a three-dimensional structure. The dependency between the S O distance and the improper S C C O torsion angle based on 739 structures containing the CC( O)NC( S)N moiety is discussed

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