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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.


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The crystal packing of the title salt, viewed along the b axis. The hydrogen bonds are shown as dashed lines (see Table 1 ▸ for details; only the major components of the disordered nitro O atoms are shown).
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fig2: The crystal packing of the title salt, viewed along the b axis. The hydrogen bonds are shown as dashed lines (see Table 1 ▸ for details; only the major components of the disordered nitro O atoms are shown).

Mentions: In the crystal, the ion pairs are linked by the N—H⋯O and N—H⋯N hydrogen bonds (Table 1 ▸ and Fig. 2 ▸). The proton­ated atom (N3) and the 2-amino group (N2) of the cation are hydrogen bonded to the carboxyl­ate oxygen atoms (O5 and O4) and the nitro­gen atom (N4) of the sulfamate anion via a pair of N—H⋯O and N—H⋯N (N3—H3A⋯O5, N2—H2B⋯O4 and N2—H2A⋯N4) hydrogen bonds (Table 1 ▸), forming an (22)ring motif. These motifs are further linked by N—H⋯O hydrogen bonds, enclosing (8) loops, and forming sheets lying parallel to (100). Weak C—H⋯O hydrogen bonds link the sheets, forming a three-dimensional structure (Fig. 2 ▸ and Table 1 ▸). The identification of such supra­molecular patterns will help us design and construct preferred hydrogen-bonding patterns of drug-like mol­ecules.


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)

The crystal packing of the title salt, viewed along the b axis. The hydrogen bonds are shown as dashed lines (see Table 1 ▸ for details; only the major components of the disordered nitro O atoms are shown).
© Copyright Policy - open-access
Related In: Results  -  Collection

License
Show All Figures
getmorefigures.php?uid=PMC4384627&req=5

fig2: The crystal packing of the title salt, viewed along the b axis. The hydrogen bonds are shown as dashed lines (see Table 1 ▸ for details; only the major components of the disordered nitro O atoms are shown).
Mentions: In the crystal, the ion pairs are linked by the N—H⋯O and N—H⋯N hydrogen bonds (Table 1 ▸ and Fig. 2 ▸). The proton­ated atom (N3) and the 2-amino group (N2) of the cation are hydrogen bonded to the carboxyl­ate oxygen atoms (O5 and O4) and the nitro­gen atom (N4) of the sulfamate anion via a pair of N—H⋯O and N—H⋯N (N3—H3A⋯O5, N2—H2B⋯O4 and N2—H2A⋯N4) hydrogen bonds (Table 1 ▸), forming an (22)ring motif. These motifs are further linked by N—H⋯O hydrogen bonds, enclosing (8) loops, and forming sheets lying parallel to (100). Weak C—H⋯O hydrogen bonds link the sheets, forming a three-dimensional structure (Fig. 2 ▸ and Table 1 ▸). The identification of such supra­molecular patterns will help us design and construct preferred hydrogen-bonding patterns of drug-like mol­ecules.

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.


Related in: MedlinePlus