Bis(2,6-dicarboxy­pyridinium) dichloride acetone monosolvate

Cuong Quoc Ton; Michael Bolte

doi:10.1107/S1600536809043220

. 2009 Oct 23;65(Pt 11):o2848. doi: 10.1107/S1600536809043220

Bis(2,6-dicarboxypyridinium) dichloride acetone monosolvate

Cuong Quoc Ton ^a, Michael Bolte ^b,^*

PMCID: PMC2971198 PMID: 21578437

Abstract

The title compound, 2C₇H₆NO₄ ⁺·2Cl⁻·C₃H₆O, crystallizes with two 2,6-dicarboxypyridinium cations, two chloride anions and one acetone molecule in the asymmetric unit. The crystal structure is characterized by alternating cations and by Cl⁻ anions, forming zigzag chains running along the a axis.

Related literature

For co-crystallization experiments, see: Ton & Bolte (2005 ▶); Tutughamiarso et al. (2009 ▶).

Experimental

Crystal data

2C₇H₆NO₄ ⁺·2Cl⁻·C₃H₆O
M _r = 465.23
Monoclinic,
a = 21.108 (4) Å
b = 6.7877 (14) Å
c = 15.224 (3) Å
β = 110.28 (3)°
V = 2046.0 (7) Å³
Z = 4
Mo Kα radiation
μ = 0.37 mm⁻¹
T = 173 K
0.30 × 0.20 × 0.20 mm

Data collection

Stoe IPDSII two-circle diffractometer
Absorption correction: multi-scan (MULABS; Spek, 2003 ▶; Blessing, 1995 ▶) T _min = 0.897, T _max = 0.930
27731 measured reflections
3867 independent reflections
3412 reflections with I > 2σ(I)
R _int = 0.041

Refinement

R[F ² > 2σ(F ²)] = 0.028
wR(F ²) = 0.082
S = 1.07
3867 reflections
277 parameters
2 restraints
H-atom parameters constrained
Δρ_max = 0.17 e Å⁻³
Δρ_min = −0.33 e Å⁻³

Data collection: X-AREA (Stoe & Cie, 2001 ▶); cell refinement: X-AREA; data reduction: X-AREA; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: XP in SHELXTL (Sheldrick, 2008 ▶); software used to prepare material for publication: SHELXL97.

Supplementary Material

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536809043220/ng2671sup1.cif

e-65-o2848-sup1.cif^{(20.3KB, cif)}

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809043220/ng2671Isup2.hkl

e-65-o2848-Isup2.hkl^{(189.6KB, 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
O2—H2⋯Cl2ⁱ	0.84	2.11	2.9469 (13)	171
O3—H3⋯Cl1ⁱⁱ	0.84	2.14	2.9727 (13)	172
O12—H12⋯Cl1	0.84	2.13	2.9696 (15)	179
O14—H14⋯Cl2	0.84	2.14	2.9775 (12)	177
N1—H1N⋯O30ⁱⁱⁱ	0.88	2.42	3.277 (2)	166
N1—H1N⋯O2	0.88	2.34	2.6685 (16)	103
N1—H1N⋯O4	0.88	2.39	2.7195 (16)	103
N2—H2N⋯O11	0.88	2.25	2.6365 (17)	106
N2—H2N⋯O13	0.88	2.26	2.6392 (16)	106

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

supplementary crystallographic information

Comment

The aim of our research is the cocrystallization of two small organic compounds in order to examine the hydrogen bonds formed between hydrogen-bond acceptors and hydrogen-bond donors (Ton & Bolte, 2005; Tutughamiarso et al., 2009). When pyridine-2,6-dicarbonyl dichlorid and resorcinol were mixed in order to obtain a hydrogen bonded supermolecular complex, it turned out that the pyridine-2,6-dicarbonyl dichlorid had been hydrolyzed to the dicarboxylic acid. The title compound crystallizes with two 2,6-dicarboxypyridinium cations, two chloride anions and one acetone molecule in the asymmetric unit. The crystal structure is characterized by alternating cations and by Cl^- anions forming zigzag chains running along the a axis. The amino H atoms do not form intermolecular hydrogen bonds, but show short distances to the O atoms of the adjacent carboxyl groups.

Experimental

Pyridine-2,6-dicarbonyl dichlorid (20 mg) and resorcinol (20 mg) were dissolved in 2 ml absolute acetone. The mixture was sealed and set aside at room temperature. After two weeks small block-shaped crystals were obtained. It turned out that the pyridine-2,6-dicarbonyl dichloride had been hydrolyzed to the dicarboxylic acid.