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

In the title compound, C(32)H(30)N(4)O(2)S(2), 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 C(i) = S (2) point-group symmetry with a crystallographic center of inversion located in the middle of...

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Autores principales: Okuniewski, Andrzej, Chojnacki, Jaroslaw, Becker, Barbara
Formato: Online Artículo Texto
Lenguaje:English
Publicado: International Union of Crystallography 2012
Materias:
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC3295418/
https://www.ncbi.nlm.nih.gov/pubmed/22412529
http://dx.doi.org/10.1107/S1600536812002954
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author Okuniewski, Andrzej
Chojnacki, Jaroslaw
Becker, Barbara
author_facet Okuniewski, Andrzej
Chojnacki, Jaroslaw
Becker, Barbara
author_sort Okuniewski, Andrzej
collection PubMed
description In the title compound, C(32)H(30)N(4)O(2)S(2), 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 C(i) = 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.
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spelling pubmed-32954182012-03-12 3,3′-Dibenzoyl-1,1′-dibenzyl-1,1′-(ethane-1,2-di­yl)­dithio­urea Okuniewski, Andrzej Chojnacki, Jaroslaw Becker, Barbara Acta Crystallogr Sect E Struct Rep Online Organic Papers In the title compound, C(32)H(30)N(4)O(2)S(2), 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 C(i) = 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. International Union of Crystallography 2012-02-04 /pmc/articles/PMC3295418/ /pubmed/22412529 http://dx.doi.org/10.1107/S1600536812002954 Text en © Okuniewski et al. 2012 http://creativecommons.org/licenses/by/2.0/uk/ This is an open-access article distributed under the terms of the Creative Commons Attribution Licence, which permits unrestricted use, distribution, and reproduction in any medium, provided the original authors and source are cited.
spellingShingle Organic Papers
Okuniewski, Andrzej
Chojnacki, Jaroslaw
Becker, Barbara
3,3′-Dibenzoyl-1,1′-dibenzyl-1,1′-(ethane-1,2-di­yl)­dithio­urea
title 3,3′-Dibenzoyl-1,1′-dibenzyl-1,1′-(ethane-1,2-di­yl)­dithio­urea
title_full 3,3′-Dibenzoyl-1,1′-dibenzyl-1,1′-(ethane-1,2-di­yl)­dithio­urea
title_fullStr 3,3′-Dibenzoyl-1,1′-dibenzyl-1,1′-(ethane-1,2-di­yl)­dithio­urea
title_full_unstemmed 3,3′-Dibenzoyl-1,1′-dibenzyl-1,1′-(ethane-1,2-di­yl)­dithio­urea
title_short 3,3′-Dibenzoyl-1,1′-dibenzyl-1,1′-(ethane-1,2-di­yl)­dithio­urea
title_sort 3,3′-dibenzoyl-1,1′-dibenzyl-1,1′-(ethane-1,2-di­yl)­dithio­urea
topic Organic Papers
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC3295418/
https://www.ncbi.nlm.nih.gov/pubmed/22412529
http://dx.doi.org/10.1107/S1600536812002954
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