2-Carboxy­pyridinium hydrogen chloranilate

Kazuma Gotoh; Hirokazu Nagoshi; Hiroyuki Ishida

doi:10.1107/S1600536809006412

. 2009 Feb 28;65(Pt 3):o614. doi: 10.1107/S1600536809006412

2-Carboxypyridinium hydrogen chloranilate

Kazuma Gotoh ^a, Hirokazu Nagoshi ^a, Hiroyuki Ishida ^a,^*

PMCID: PMC2968548 PMID: 21582266

Abstract

In the crystal structure of the title salt, C₆H₆NO₂ ⁺·C₆HCl₂O₄ ⁻, the pyridine ring and the mean plane of the hydrogen chloranilate anion form a dihedral angle of 77.40 (8)°. The ionic components are held together by N—H⋯O and O—H⋯O hydrogen bonds, forming a supramolecular ladder. C—H⋯O interactions are also present.

Related literature

For the structures of related carboxypyridinium hydrogen chloranilates, see: Gotoh et al. (2006 ▶); Tabuchi et al. (2005 ▶); Ishida (2009 ▶).

Experimental

Crystal data

C₆H₆NO₂ ⁺·C₆HCl₂O₄ ⁻
M _r = 332.10
Monoclinic,
a = 9.4166 (8) Å
b = 19.6900 (16) Å
c = 6.7089 (6) Å
β = 99.043 (3)°
V = 1228.45 (18) Å³
Z = 4
Mo Kα radiation
μ = 0.56 mm⁻¹
T = 103 K
0.30 × 0.30 × 0.23 mm

Data collection

Rigaku R-AXIS RAPID-II diffractometer
Absorption correction: multi-scan (ABSCOR; Higashi, 1995 ▶) T _min = 0.847, T _max = 0.880
9710 measured reflections
3433 independent reflections
2228 reflections with I > 2σ(I)
R _int = 0.047

Refinement

R[F ² > 2σ(F ²)] = 0.045
wR(F ²) = 0.144
S = 1.10
3433 reflections
202 parameters
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.47 e Å⁻³
Δρ_min = −0.92 e Å⁻³

Data collection: PROCESS-AUTO (Rigaku/MSC, 2004 ▶); cell refinement: PROCESS-AUTO; data reduction: CrystalStructure (Rigaku/MSC, 2004 ▶); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: ORTEP-3 (Farrugia, 1997 ▶); software used to prepare material for publication: CrystalStructure and PLATON (Spek, 2009 ▶).

Supplementary Material

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536809006412/tk2376sup1.cif

e-65-0o614-sup1.cif^{(16.9KB, cif)}

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809006412/tk2376Isup2.hkl

e-65-0o614-Isup2.hkl^{(168.4KB, hkl)}

Additional supplementary materials: crystallographic information; 3D view; checkCIF report

Table 1. Hydrogen-bond geometry (Å, °).

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1⋯O1	0.92 (4)	2.11 (3)	2.932 (2)	147 (3)
O2—H2⋯O5ⁱ	0.79 (3)	2.05 (3)	2.746 (2)	148 (3)
O6—H6⋯O4ⁱⁱ	0.90 (3)	1.63 (3)	2.528 (2)	177.1 (15)
C8—H8⋯O4ⁱⁱⁱ	0.95	2.50	3.338 (3)	147
C9—H9⋯O3^iv	0.95	2.33	3.227 (3)	156
C11—H11⋯O1^v	0.95	2.46	3.374 (3)	162

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Symmetry codes: (i) Inline graphic ; (ii) ; (iii) ; (iv) ; (v) .

Acknowledgments

This work was supported by a Grant-in-Aid for Scientific Research (C) (No. 19550018) from the Japan Society for the Promotion of Science.

supplementary crystallographic information

Comment

The title salt, (I), was prepared in order to extend our study on D—H···A hydrogen bonding (D = N, O or C; A = N, O or Cl) in chloranilic acid – substituted-pyridine systems (Gotoh et al., 2006; Tabuchi et al., 2005).

Compound (I) comprises 2-carboxypyridinium cations and hydrogen chloranilate anions in the ratio 1:1. Ions directly connected by an N—H···O hydrogen bond, Fig. 1, form a dihedral angle between their respective mean planes of 77.40 (8)°. In the cation, the carboxy O5/O6/C12 plane forms a dihedral angle of 11.44 (6)° with the pyridine ring, which is similar to those of 2.74 (6) and 10.01 (3)° observed in 3-carboxypyridinium hydrogen chloranilate and 4-carboxypyridinium hydrogen chloranilate monohydrate, respectively (Ishida, 2009). The ions are further connected by O—H···O hydrogen bonds (Table 1) to afford a supramolecular ladder running along the c axis (Fig. 2). The ladders are linked by weaker N—H···O hydrogen bonds and C—H···O contacts to form a 3-D network (Table 1).

Experimental

Crystals were obtained by slow evaporation from a methanol solution (ca 30 ml) containing a 1:1 molar ratio of chloranilic acid (0.302 g) and picolinic acid (0.179 g).