Strong N–H⋯N hydrogen bonds and weak N–H⋯S  C interactions in controlling the structure of the co-crystals of dithiooxamide with nitrogen heterocycles

Barbara Piotrkowska; Aleksandra Wasilewska; Maria Gdaniec; Tadeusz Połoński

doi:10.1039/B806061D

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Strong N–H⋯N hydrogen bonds and weak N–H⋯S C interactions in controlling the structure of the co-crystals of dithiooxamide with nitrogen heterocycles†

Barbara Piotrkowska,^a Aleksandra Wasilewska,^a Maria Gdaniec*^b and Tadeusz Połoński*^a

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* Corresponding authors

^a Department of Chemistry, Gdańsk University of Technology, Gdansk, Poland
E-mail: tadpol@chem.pg.gda.pl

^b Faculty of Chemistry, A. Mickiewicz University, Poznań, Poland
E-mail: magdan@amu.edu.pl

Abstract

A series of co-crystals of dithiooxamide (dtox) with azaheterocycles 1–6 (1 = 4,4′-dipyridyl, 2 = 1,2-bis(4-pyridyl)ethane, 3 = 2,7-diazapyrene, 4 = 1,4-diazabicyclo[2.2.2]octane, 5 = 1,3,5,7-tetraazatricyclo[3.3.1.13,7]decane, 6 = 1,10-phenanthroline) were prepared and their structures were studied by X-ray crystallography. The structures of 1·dtox–5·dtox are characterized by infinite 1D assemblies of the alternating component molecules linked by the N–H⋯N hydrogen bonds whereas in the case of 6₂·dtox, formation of heterotrimers was observed. In the case of 1·dtox–5·dtox the dtox molecules are arranged into pleated or planar tapes by weak N–H⋯S interactions with H⋯S distances in the range of 2.80–3.15 Å and the N–H⋯S angle of 106–135°. In the crystals of 1·dtox–4·dtox a combination of the two-component chain motif with the dtox tapes generates 2D layers whereas in 5·dtox a 3D network is formed.

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Article information

DOI: https://doi.org/10.1039/B806061D
Article type: Paper
Submitted: 10 Apr 2008
Accepted: 25 Jul 2008
First published: 08 Aug 2008

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CrystEngComm, 2008,10, 1421-1428

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Strong N–H⋯N hydrogen bonds and weak N–H⋯S C interactions in controlling the structure of the co-crystals of dithiooxamide with nitrogen heterocycles

B. Piotrkowska, A. Wasilewska, M. Gdaniec and T. Połoński, CrystEngComm, 2008, 10, 1421 DOI: 10.1039/B806061D

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