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Crystal structure of 2-amino-5-nitro-pyridinium sulfamate.

Rajkumar MA, NizamMohideen M, Xavier SS, Anbarasu S, Devarajan DP - Acta Crystallogr E Crystallogr Commun (2015)

Bottom Line: A proton transfer from sulfamic acid to the pyridine N atom occurred, resulting in the formation of a salt.As expected, this protonation leads to the widening of the C-N-C angle of the pyridine ring, to 122.9 (3)°, with the pyridinium ring being essentially planar (r.m.s. deviation = 0.025 Å).The O atoms of the nitro group are disordered over two sets of sites with a refined occupancy ratio of 0.737 (19):0.263 (19).

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Affiliation: Physics Research Centre, Department of Physics, St. Xavier's College (Autonomous), Palayamkottai 627 002, Tamil Nadu, India.

ABSTRACT
The title mol-ecular salt, C5H6N3O2 (+) ·H2NO3S(-), was obtained from the reaction of sulfamic acid with 2-amino-5-nitro-pyridine. A proton transfer from sulfamic acid to the pyridine N atom occurred, resulting in the formation of a salt. As expected, this protonation leads to the widening of the C-N-C angle of the pyridine ring, to 122.9 (3)°, with the pyridinium ring being essentially planar (r.m.s. deviation = 0.025 Å). In the crystal, the ion pairs are joined by three N-H⋯O and one N-H⋯N hydrogen bonds in which the pyridinium N atom and the amino N atom act as donors, and are hydrogen bonded to the carboxyl-ate O atoms and the N atom of the sulfamate anion, thus generating an R (3) 3(22) ring motif. These motifs are linked by further N-H⋯O hydrogen bonds enclosing R (3) 3(8) loops, forming sheets parallel to (100). The sheets are linked via weak C-H⋯O hydrogen bonds, forming a three-dimensional structure. The O atoms of the nitro group are disordered over two sets of sites with a refined occupancy ratio of 0.737 (19):0.263 (19).

No MeSH data available.


View of the mol­ecular structure of the title mol­ecular salt, with atom labelling. Displacement ellipsoids are drawn at the 50% probability level.
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fig1: View of the mol­ecular structure of the title mol­ecular salt, with atom labelling. Displacement ellipsoids are drawn at the 50% probability level.

Mentions: The asymmetric unit of the title compound, Fig. 1 ▸, consists of a 2-amino-5-nitro­pyridin-1-ium cation and a sulfamate anion. The bond lengths and angles are within normal ranges and comparable with those in closely related structures (Babu et al., 2014a ▸,b ▸; Rajkumar et al., 2014 ▸). A proton transfer from the sulfamic acid to the pyridine atom N3 resulted in the formation of a salt. This protonation leads to the widening of the C5—N3—C1 angle of the pyridine ring to 122.9 (3)°, compared with 115.25 (13)° in unprotonated amino­pyridine (Anderson et al., 2005 ▸). This type of protonation is observed in various amino­pyridine acid complexes (Babu et al., 2014a ▸,b ▸; Rajkumar et al., 2014 ▸). In the sulfamate anion the S—O distances vary from 1.440 (3) to 1.460 (2) Å, and O—S—O angles vary from 111.59 (15) to 114.22 (15) °.


Crystal structure of 2-amino-5-nitro-pyridinium sulfamate.

Rajkumar MA, NizamMohideen M, Xavier SS, Anbarasu S, Devarajan DP - Acta Crystallogr E Crystallogr Commun (2015)

View of the mol­ecular structure of the title mol­ecular salt, with 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=PMC4384627&req=5

fig1: View of the mol­ecular structure of the title mol­ecular salt, with atom labelling. Displacement ellipsoids are drawn at the 50% probability level.
Mentions: The asymmetric unit of the title compound, Fig. 1 ▸, consists of a 2-amino-5-nitro­pyridin-1-ium cation and a sulfamate anion. The bond lengths and angles are within normal ranges and comparable with those in closely related structures (Babu et al., 2014a ▸,b ▸; Rajkumar et al., 2014 ▸). A proton transfer from the sulfamic acid to the pyridine atom N3 resulted in the formation of a salt. This protonation leads to the widening of the C5—N3—C1 angle of the pyridine ring to 122.9 (3)°, compared with 115.25 (13)° in unprotonated amino­pyridine (Anderson et al., 2005 ▸). This type of protonation is observed in various amino­pyridine acid complexes (Babu et al., 2014a ▸,b ▸; Rajkumar et al., 2014 ▸). In the sulfamate anion the S—O distances vary from 1.440 (3) to 1.460 (2) Å, and O—S—O angles vary from 111.59 (15) to 114.22 (15) °.

Bottom Line: A proton transfer from sulfamic acid to the pyridine N atom occurred, resulting in the formation of a salt.As expected, this protonation leads to the widening of the C-N-C angle of the pyridine ring, to 122.9 (3)°, with the pyridinium ring being essentially planar (r.m.s. deviation = 0.025 Å).The O atoms of the nitro group are disordered over two sets of sites with a refined occupancy ratio of 0.737 (19):0.263 (19).

View Article: PubMed Central - HTML - PubMed

Affiliation: Physics Research Centre, Department of Physics, St. Xavier's College (Autonomous), Palayamkottai 627 002, Tamil Nadu, India.

ABSTRACT
The title mol-ecular salt, C5H6N3O2 (+) ·H2NO3S(-), was obtained from the reaction of sulfamic acid with 2-amino-5-nitro-pyridine. A proton transfer from sulfamic acid to the pyridine N atom occurred, resulting in the formation of a salt. As expected, this protonation leads to the widening of the C-N-C angle of the pyridine ring, to 122.9 (3)°, with the pyridinium ring being essentially planar (r.m.s. deviation = 0.025 Å). In the crystal, the ion pairs are joined by three N-H⋯O and one N-H⋯N hydrogen bonds in which the pyridinium N atom and the amino N atom act as donors, and are hydrogen bonded to the carboxyl-ate O atoms and the N atom of the sulfamate anion, thus generating an R (3) 3(22) ring motif. These motifs are linked by further N-H⋯O hydrogen bonds enclosing R (3) 3(8) loops, forming sheets parallel to (100). The sheets are linked via weak C-H⋯O hydrogen bonds, forming a three-dimensional structure. The O atoms of the nitro group are disordered over two sets of sites with a refined occupancy ratio of 0.737 (19):0.263 (19).

No MeSH data available.