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Synthesis and crystal structure of (( E )-{2-[( E )-(4-hy ­ droxynaphthalen-1-yl)methyl ­ idene]hydrazin-1-yl}(methyl ­ sulfan ­ yl)methyl ­ idene)azanium hydrogen sulfate monohydrate

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ABSTRACT

In the title hydrated mol­ecular salt, C13H14N3S+·HSO4−·H2O, the protonation of the azomethine N atom in sulfuric acid medium involves the formation of the bis­ulfate anion. The mol­ecular structure of the cation is obtained from the thiol tautomer of thio­semicarbazone wherein the naphthalene moiety and the conjugation of the bonds contribute to the planarity of the mol­ecular skeleton. In the crystal, the cation, anion and water mol­ecule of crystallization are linked by a series of O—H⋯O and N—H⋯O hydrogen bonds, forming a three-dimensional network. Within this network, there are also C—H⋯π inter­actions present involving symmetry-related naphthalene rings.

No MeSH data available.


A view of the mol­ecular structure of the title mol­ecular salt, with the atom labelling. Displacement ellipsoids are drawn at the 50% probability level.
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fig2: A view of the mol­ecular structure of the title mol­ecular salt, with the atom labelling. Displacement ellipsoids are drawn at the 50% probability level.

Mentions: The mol­ecular structure of the title mol­ecular salt is illustrated in Fig. 2 ▸. It is composed of three entities: a bis­ulfate anion, a thio­semicarbazone cation and a water mol­ecule of crystallization. The cationic entity shows an E conformation with respect to the C12=N13 bond and is approximately planar, the maximum deviation from the mean plane through the 18 non-hydrogen atoms being 0.118 (2) Å for atom C12. This planarity is due to electron delocalization along the cationic entity backbone. Bond lengths and angles are close to those observed for similar (methyl­idene)hydrazinecarbo­thio­amide derivatives (Gangadharan et al., 2015 ▸; Joseph et al., 2004 ▸; Houari et al., 2013 ▸.)


Synthesis and crystal structure of (( E )-{2-[( E )-(4-hy ­ droxynaphthalen-1-yl)methyl ­ idene]hydrazin-1-yl}(methyl ­ sulfan ­ yl)methyl ­ idene)azanium hydrogen sulfate monohydrate
A view of the mol­ecular structure of the title mol­ecular salt, with 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=PMC5120717&req=5

fig2: A view of the mol­ecular structure of the title mol­ecular salt, with the atom labelling. Displacement ellipsoids are drawn at the 50% probability level.
Mentions: The mol­ecular structure of the title mol­ecular salt is illustrated in Fig. 2 ▸. It is composed of three entities: a bis­ulfate anion, a thio­semicarbazone cation and a water mol­ecule of crystallization. The cationic entity shows an E conformation with respect to the C12=N13 bond and is approximately planar, the maximum deviation from the mean plane through the 18 non-hydrogen atoms being 0.118 (2) Å for atom C12. This planarity is due to electron delocalization along the cationic entity backbone. Bond lengths and angles are close to those observed for similar (methyl­idene)hydrazinecarbo­thio­amide derivatives (Gangadharan et al., 2015 ▸; Joseph et al., 2004 ▸; Houari et al., 2013 ▸.)

View Article: PubMed Central - HTML - PubMed

ABSTRACT

In the title hydrated mol­ecular salt, C13H14N3S+·HSO4−·H2O, the protonation of the azomethine N atom in sulfuric acid medium involves the formation of the bis­ulfate anion. The mol­ecular structure of the cation is obtained from the thiol tautomer of thio­semicarbazone wherein the naphthalene moiety and the conjugation of the bonds contribute to the planarity of the mol­ecular skeleton. In the crystal, the cation, anion and water mol­ecule of crystallization are linked by a series of O—H⋯O and N—H⋯O hydrogen bonds, forming a three-dimensional network. Within this network, there are also C—H⋯π inter­actions present involving symmetry-related naphthalene rings.

No MeSH data available.