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Crystal structure of 4-hy-droxy-pyridin-1-ium 3,5-di-carb-oxy-benzoate.

Staun SL, Oliver AG - Acta Crystallogr E Crystallogr Commun (2015)

Bottom Line: The structure of the title salt, C5H6NO(+)·C9H5O6 (-), (I), shows that 4-hy-droxy-pyridine has abstracted an H atom from benzene-1,3,5-tri-carb-oxy-lic acid, yielding a pyridinium cation and carboxyl-ate anion.The hydrogen bonds that comprise the core of the network are considered strong, with O-H⋯O and N-H⋯O donor-to-acceptor distances ranging from 2.533 (2) to 2.700 (2) Å.Packing is further enhanced by π-stacking of the cations and anions with like species [centroid-centroid distance = 3.6206 (13) Å].

View Article: PubMed Central - HTML - PubMed

Affiliation: Department of Chemistry and Biochemistry, University of Notre Dame, Notre Dame, IN 46556-5670, USA.

ABSTRACT
The structure of the title salt, C5H6NO(+)·C9H5O6 (-), (I), shows that 4-hy-droxy-pyridine has abstracted an H atom from benzene-1,3,5-tri-carb-oxy-lic acid, yielding a pyridinium cation and carboxyl-ate anion. The two ions form an extensive three-dimensional hydrogen-bonded network throughout the crystal. The hydrogen bonds that comprise the core of the network are considered strong, with O-H⋯O and N-H⋯O donor-to-acceptor distances ranging from 2.533 (2) to 2.700 (2) Å. Packing is further enhanced by π-stacking of the cations and anions with like species [centroid-centroid distance = 3.6206 (13) Å].

No MeSH data available.


A view of (I) approximately along the crystallographic c axis. Color code: blue represents the (28) ring, purple the (44) ring, and green the bridging 4-hy­droxy­pyridinium cations.
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fig2: A view of (I) approximately along the crystallographic c axis. Color code: blue represents the (28) ring, purple the (44) ring, and green the bridging 4-hy­droxy­pyridinium cations.

Mentions: Pertinent features of this extended network are an (28) ring comprised of 3,5-di­carb­oxy­benzoate ions (Fig. 2 ▸) (Bernstein et al., 1995 ▸). The carb­oxy­lic acid groups are involved in the hydrogen bonding within this ring. There is also an (44) ring of 3,5-di­carb­oxy­benzoate ions, that incorporate a different chain of carb­oxy­lic acid groups. These rings are bridged by the 4-hy­droxy­pyridinium cations resulting in the three-dimensional network. The hydrogen bonds within the structure are surprisingly strong, with O—H⋯O and N—H⋯O distances ranging from 2.533 (2) to 2.700 (2) Å (Table 1 ▸).


Crystal structure of 4-hy-droxy-pyridin-1-ium 3,5-di-carb-oxy-benzoate.

Staun SL, Oliver AG - Acta Crystallogr E Crystallogr Commun (2015)

A view of (I) approximately along the crystallographic c axis. Color code: blue represents the (28) ring, purple the (44) ring, and green the bridging 4-hy­droxy­pyridinium cations.
© Copyright Policy - open-access
Related In: Results  -  Collection

License
Show All Figures
getmorefigures.php?uid=PMC4518931&req=5

fig2: A view of (I) approximately along the crystallographic c axis. Color code: blue represents the (28) ring, purple the (44) ring, and green the bridging 4-hy­droxy­pyridinium cations.
Mentions: Pertinent features of this extended network are an (28) ring comprised of 3,5-di­carb­oxy­benzoate ions (Fig. 2 ▸) (Bernstein et al., 1995 ▸). The carb­oxy­lic acid groups are involved in the hydrogen bonding within this ring. There is also an (44) ring of 3,5-di­carb­oxy­benzoate ions, that incorporate a different chain of carb­oxy­lic acid groups. These rings are bridged by the 4-hy­droxy­pyridinium cations resulting in the three-dimensional network. The hydrogen bonds within the structure are surprisingly strong, with O—H⋯O and N—H⋯O distances ranging from 2.533 (2) to 2.700 (2) Å (Table 1 ▸).

Bottom Line: The structure of the title salt, C5H6NO(+)·C9H5O6 (-), (I), shows that 4-hy-droxy-pyridine has abstracted an H atom from benzene-1,3,5-tri-carb-oxy-lic acid, yielding a pyridinium cation and carboxyl-ate anion.The hydrogen bonds that comprise the core of the network are considered strong, with O-H⋯O and N-H⋯O donor-to-acceptor distances ranging from 2.533 (2) to 2.700 (2) Å.Packing is further enhanced by π-stacking of the cations and anions with like species [centroid-centroid distance = 3.6206 (13) Å].

View Article: PubMed Central - HTML - PubMed

Affiliation: Department of Chemistry and Biochemistry, University of Notre Dame, Notre Dame, IN 46556-5670, USA.

ABSTRACT
The structure of the title salt, C5H6NO(+)·C9H5O6 (-), (I), shows that 4-hy-droxy-pyridine has abstracted an H atom from benzene-1,3,5-tri-carb-oxy-lic acid, yielding a pyridinium cation and carboxyl-ate anion. The two ions form an extensive three-dimensional hydrogen-bonded network throughout the crystal. The hydrogen bonds that comprise the core of the network are considered strong, with O-H⋯O and N-H⋯O donor-to-acceptor distances ranging from 2.533 (2) to 2.700 (2) Å. Packing is further enhanced by π-stacking of the cations and anions with like species [centroid-centroid distance = 3.6206 (13) Å].

No MeSH data available.