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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.

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A view along the a axis of the crystal packing of the title mol­ecular salt. The hydrogen bonds are drawn as dashed lines (see Table 1 ▸) and the C-bound H atoms have been omitted for clarity.
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fig3: A view along the a axis of the crystal packing of the title mol­ecular salt. The hydrogen bonds are drawn as dashed lines (see Table 1 ▸) and the C-bound H atoms have been omitted for clarity.

Mentions: In the crystal, there is an extensive hydrogen-bonding network present. 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 (Table 1 ▸ and Fig. 3 ▸). Within this network there are also C—H⋯π inter­actions present involving symmetry-related naphthalene rings (Table 1 ▸).


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 along the a axis of the crystal packing of the title mol­ecular salt. The hydrogen bonds are drawn as dashed lines (see Table 1 ▸) and the C-bound H atoms have been omitted for clarity.
© Copyright Policy - open-access
Related In: Results  -  Collection

License
Show All Figures
getmorefigures.php?uid=PMC5120717&req=5

fig3: A view along the a axis of the crystal packing of the title mol­ecular salt. The hydrogen bonds are drawn as dashed lines (see Table 1 ▸) and the C-bound H atoms have been omitted for clarity.
Mentions: In the crystal, there is an extensive hydrogen-bonding network present. 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 (Table 1 ▸ and Fig. 3 ▸). Within this network there are also C—H⋯π inter­actions present involving symmetry-related naphthalene rings (Table 1 ▸).

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.


Related in: MedlinePlus