4-[3,5-Bis(ethoxy­carbon­yl)-2,6-dimethyl-4-pyrid­yl]pyridinium nitrate

Yumei Li

doi:10.1107/S1600536810015035

. 2010 Apr 30;66(Pt 5):o1224. doi: 10.1107/S1600536810015035

4-[3,5-Bis(ethoxycarbonyl)-2,6-dimethyl-4-pyridyl]pyridinium nitrate

Yumei Li ^a,^*

PMCID: PMC2979292 PMID: 21579250

Abstract

In the title molecular salt, C₁₈H₂₁N₂O₄ ⁺·NO₃ ⁻, the dihedral angle between the two pyridine rings is 61.24 (8)°. In the crystal, the cation and anion are linked by intermolecular N—H⋯O hydrogen bonds.

Related literature

For general background to metal-organic frameworks, see: Zhang et al. (2003 ▶).

Experimental

Crystal data

C₁₈H₂₁N₂O₄ ⁺·NO₃ ⁻
M _r = 391.38
Orthorhombic,
a = 9.075 (9) Å
b = 15.496 (15) Å
c = 14.125 (13) Å
V = 1987 (3) Å³
Z = 4
Mo Kα radiation
μ = 0.10 mm⁻¹
T = 296 K
0.37 × 0.33 × 0.24 mm

Data collection

Bruker APEXII CCD diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2001 ▶) T _min = 0.963, T _max = 0.975
9196 measured reflections
3395 independent reflections
2877 reflections with I > 2σ(I)
R _int = 0.156

Refinement

R[F ² > 2σ(F ²)] = 0.043
wR(F ²) = 0.115
S = 1.00
3395 reflections
258 parameters
1 restraint
H-atom parameters constrained
Δρ_max = 0.17 e Å⁻³
Δρ_min = −0.21 e Å⁻³

Data collection: APEX2 (Bruker, 2004 ▶); cell refinement: SAINT-Plus (Bruker, 2001 ▶); data reduction: SAINT-Plus; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: SHELXTL (Sheldrick, 2008 ▶); software used to prepare material for publication: SHELXTL.

Supplementary Material

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536810015035/hb5413sup1.cif

e-66-o1224-sup1.cif^{(20.5KB, cif)}

Structure factors: contains datablocks I. DOI: 10.1107/S1600536810015035/hb5413Isup2.hkl

e-66-o1224-Isup2.hkl^{(166.5KB, 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
N2—H2A⋯O5ⁱ	0.86	1.90	2.752 (3)	171

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Symmetry code: (i) Inline graphic .

supplementary crystallographic information

Comment

In recent years, the design and construction of metal-organic frameworks through the coordination of metal ions with multifunctional organic ligands have received extensive attention due to their impressive structural diversities in architectures and their potential applications as functional materials (Zhang et al., 2003). Whereas, it is more important to design the novel organic ligand. Here, we describe the recystallization and structural characterization of the title compound.

The molecular structure is shown in Fig 1. The dihedral angle between the two pyridine rings is 61.24 (8) °. N—H···O and N—H···N hydrogen bonding between the cations and anions leads to a consolidation of the structure (Fig. 2; Table 1).

Experimental

A mixture of 2,6-dimethyl-4-(4-pyridyl)pyridine-3,5-dicarboxylate (1 mmol, 0.39 g) and ammonium nitrate (2 mmol, 0.16 g) in 20 ml ethanol was refluxed for half an hour. The obtained filtrate was evaporated in one open flask at room temperature. One week later, yellow blocks of (I) were obained. Anal. C₂₀H₂₂NO₇: C, 55.61; H, 5.41; N, 7.21 %. Found: C, 55.56; H, 5.33; N, 7.10 %.