Bis(4-aminopyridinium) bis(hydrogen oxalate) monohydrate

Fun, Hoong‐Kun; John, Jain; Jebas, Samuel Robinson; Balasubramanian, T.

doi:10.1107/s1600536809007247

Cited by 5 publications

(8 citation statements)

References 11 publications

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“…The uncoordinated 4-aminopyridinium cations are located between the anions (Fig. 2), their geometric parameters do not show unusual features, they are in accordance with those previously reported (Fun et al, 2008(Fun et al, , 2009(Fun et al, , 2010Quah et al, 2008;Ramesh et al, 2010;Rotondo et al, 2009;Pan et al, 2008).…”

Section: Methodssupporting

confidence: 90%

Talatisamine, a C₁₉-diterpenoid alkaloid from Chinese traditional herbal `Chuanwu'

Lei¹,

Luo²,

Qing-quan³

et al. 2011

Acta Cryst E

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The title compound [systematic name: (1S,4S,5R,7S,8S,9R,10R,11S,13S,14S,16S,17R)-N-methyl-8,14-dihydroxy-1,16-trimethoxy-4-(methoxymethylene)aconitane], C24H39NO5, was isolated from the roots of Aconitum carmichaelii Debx., which is known as ‘Chuanwu’ in Chinese traditional herbal medicine. The molecule has an aconitane carbon skeleton with four six-membered rings and two five-membered rings, including a six-membered N-containing heterocyclic ring. Both five-membered rings adopt envelope conformations. The four six-membered adopt chair conformations. Two intramolecular O—H⋯O hydrogen bonds occur.

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Section: Methodssupporting

confidence: 90%

Talatisamine, a C₁₉-diterpenoid alkaloid from Chinese traditional herbal `Chuanwu'

Lei¹,

Luo²,

Qing-quan³

et al. 2011

Acta Cryst E

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“…The uncoordinated 4-aminopyridinium cations are located between the anions (Fig. 2), their geometric parameters do not show unusual features, they are in accordance with those previously reported (Fun et al, 2008(Fun et al, , 2009(Fun et al, , 2010Jebas et al, 2009;Quah et al, 2008;Ramesh et al, 2010;Rotondo et al, 2009;Pan et al, 2008).…”

Section: Data Collectionsupporting

confidence: 91%

“…For C-O distances in oxalate anions, see: Marinescu et al (2000). For geometric parameters of the 4-aminopyridinium cation, see: Fun et al (2008Fun et al ( , 2009Fun et al ( , 2010; Jebas et al (2009); Quah et al (2008); Ramesh et al (2010); Rotondo et al (2009); Pan et al (2008). For discussion of hydrogen bonding, see: Blessing (1986); Brown (1976).…”

Section: Related Literaturementioning

confidence: 99%

4-Aminopyridiniumtrans-diaquadioxalatochromate(III) monohydrate

et al. 2011

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In the non-centrosymmetric structure of the title compound, (C5H7N2)[Cr(C2O4)2(H2O)2]·H2O, the CrIII ion has a slightly distorted octahedral coordination environment defined by two chelating oxalato ligands in equatorial positions and two water molecules in axial positions. An extensive three-dimensional network of hydrogen bonds involving all the water molecules, the 4-aminopyridinium cation and some of the oxalate O atoms contributes to the stabilization of the structure. π–π interactions between adjacent pyridine rings provide additional stability of the crystal packing, with a closest distance between pyridine mean planes of 3.613 (1) Å.

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“…The protonation is evidenced by the widening of the internal angles (C3B-N4B-C5B and C3D-N4D-C5D) of the pyridine rings to 120.5 (4) in molecule B and 120.4 (3) in molecule D of (I), and of the C2-N1-C6 angle to 120.52 (19) in molecule (II), compared with 115.25 (13) in unprotonated 4-aminopyridine (Anderson et al, 2005;Chao & Schempp, 1977). Similar protonation is observed in various 4-aminopyridine-acid complexes, such as 4-aminopyridinium hydrogen succinate (Fun et al, 2009a) and bis(4-aminopyridinium) bis(hydrogen oxalate) monohydrate (Fun et al, 2009b).…”

Section: Commentsupporting

confidence: 54%

4-Aminopyridinium 4-aminobenzoate dihydrate and 4-aminopyridinium nicotinate

Jebas

Sinthiya²,

Nayagam³

et al. 2009

Acta Crystallogr C

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In the title compounds, 4-aminopyridinium 4-aminobenzoate dihydrate, C(7)H(6)NO(2)(-).C(5)H(7)N(2)(+).2H(2)O, (I), and 4-aminopyridinium nicotinate, C(5)H(7)N(2)(+).C(6)H(4)NO(2)(-), (II), the aromatic N atoms of the 4-aminopyridinium cations are protonated. In (I), the asymmetric unit is composed of two 4-aminopyridinium cations, two 4-aminobenzoate anions and four water molecules, and the compound crystallizes in a noncentrosymmetric space group. The two sets of independent molecules of (I) are related by a centre of symmetry which is not part of the space group. In (I), the protonated pyridinium ring H atoms are involved in bifurcated hydrogen bonding with carboxylate O atoms to form an R(1)(2)(4) ring motif. The water molecules link the ions to form a two-dimensional network along the (101) plane. In (II), an intramolecular bifurcated hydrogen bond generates an R(1)(2)(4) ring motif and inter-ion hydrogen bonding generates an R(4)(2)(16) ring motif. The packing of adduct (II) is consolidated via N-H...O and N-H...N hydrogen bonds to form a two-dimensional network along the (102) plane.

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Bis(4-aminopyridinium) bis(hydrogen oxalate) monohydrate

Abstract: Key indicators: single-crystal X-ray study; T = 100 K; mean (C-C) = 0.001 Å; R factor = 0.034; wR factor = 0.096; data-to-parameter ratio = 15.5.In the title compound, ExperimentalCrystal data

Cited by 5 publications

References 11 publications

Talatisamine, a C₁₉-diterpenoid alkaloid from Chinese traditional herbal `Chuanwu'

Talatisamine, a C₁₉-diterpenoid alkaloid from Chinese traditional herbal `Chuanwu'

4-Aminopyridiniumtrans-diaquadioxalatochromate(III) monohydrate

4-Aminopyridinium 4-aminobenzoate dihydrate and 4-aminopyridinium nicotinate

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Bis(4-aminopyridinium) bis(hydrogen oxalate) monohydrate

Abstract: Key indicators: single-crystal X-ray study; T = 100 K; mean (C-C) = 0.001 Å; R factor = 0.034; wR factor = 0.096; data-to-parameter ratio = 15.5.In the title compound, ExperimentalCrystal data

Cited by 5 publications

References 11 publications

Talatisamine, a C19-diterpenoid alkaloid from Chinese traditional herbal `Chuanwu'

Talatisamine, a C19-diterpenoid alkaloid from Chinese traditional herbal `Chuanwu'

4-Aminopyridiniumtrans-diaquadioxalatochromate(III) monohydrate

4-Aminopyridinium 4-aminobenzoate dihydrate and 4-aminopyridinium nicotinate

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Talatisamine, a C₁₉-diterpenoid alkaloid from Chinese traditional herbal `Chuanwu'

Talatisamine, a C₁₉-diterpenoid alkaloid from Chinese traditional herbal `Chuanwu'