2,4,5-Tri-4-pyridyl-1H-imidazole monohydrate

Qiang Huang

doi:10.1107/S1600536809032267

. 2009 Sep 5;65(Pt 10):o2329. doi: 10.1107/S1600536809032267

2,4,5-Tri-4-pyridyl-1H-imidazole monohydrate

Qiang Huang ^a,^*

PMCID: PMC2970424 PMID: 21577800

Abstract

The title compound, C₁₈H₁₃N₅·H₂O, was synthesized by the condensation of pyridine-4-carbaldehyde and ammonium acetate, forming a multipyridyl ligand. In the crystal, molecules are linked into chains by O—H⋯N hydrogen bonds. The chains are linked by weak C—H⋯N interactions, generating a layer structure.

Related literature

2,4,5-Tri-4-pyridyl-imidazole is used in the construction of metal-organic coordination polymers, see: Liang et al. (2009 ▶).

Experimental

Crystal data

C₁₈H₁₃N₅·H₂O
M _r = 317.35
Triclinic,
a = 8.910 (2) Å
b = 9.401 (2) Å
c = 10.638 (2) Å
α = 72.027 (4)°
β = 70.624 (4)°
γ = 77.716 (4)°
V = 793.4 (3) Å³
Z = 2
Mo Kα radiation
μ = 0.09 mm⁻¹
T = 293 K
0.30 × 0.26 × 0.22 mm

Data collection

Bruker APEXII area-detector diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2004 ▶) T _min = 0.974, T _max = 0.981
4313 measured reflections
3067 independent reflections
1720 reflections with I > 2σ(I)
R _int = 0.025

Refinement

R[F ² > 2σ(F ²)] = 0.045
wR(F ²) = 0.059
S = 1.02
3067 reflections
217 parameters
3 restraints
H-atom parameters constrained
Δρ_max = 0.15 e Å⁻³
Δρ_min = −0.15 e Å⁻³

Data collection: APEX2 (Bruker, 2004 ▶); cell refinement: SAINT (Bruker, 2004 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: SHELXL97; software used to prepare material for publication: SHELXL97 and publCIF (Westrip, 2009 ▶).

Supplementary Material

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536809032267/hg2553sup1.cif

e-65-o2329-sup1.cif^{(18.9KB, cif)}

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809032267/hg2553Isup2.hkl

e-65-o2329-Isup2.hkl^{(150.5KB, hkl)}

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

Table 1. Selected torsion angles (°).

C4—C3—C6—N2	−12.2 (4)
C14—C7—C8—C9	1.8 (5)
N1—C8—C9—C13	−88.5 (3)
N2—C7—C14—C18	−7.7 (3)

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Table 2. Hydrogen-bond geometry (Å, °).

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1C⋯O1	0.94	1.82	2.756 (2)	173
C10—H10⋯N2ⁱ	0.93	2.59	3.467 (3)	158
O1—H1B⋯N4ⁱⁱ	0.91	1.96	2.869 (2)	174
O1—H1A⋯N5ⁱⁱⁱ	0.87	1.94	2.808 (2)	174

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

Acknowledgments

The author gratefully acknowledges financial support from the Educational Commission of Jiangxi Province of China (GJJ08448) and the Natural Science Foundation of Jiangxi Province of China (2008GQC0002).

supplementary crystallographic information

Comment

2,4,5-tri(4-pyridyl)imidazole is a multipyridyl compound, which is useful to construct new metal-organic coordination polymers (Liang et al., 2009). In this paper, we report the synthesis and X-ray crystal structure analysis of the title compound, (I,) 2,4,5-tri(4-pyridyl)imidazole with one co-crystallized water molecule.

In 2,4,5-tri(4-pyridyl)imidazole three pyridyl groups are directly connected with the imidazole ring. The dihedral angles between the mean planes of pyridyl ring A and imidazole ring D is 11.6 (4)°, that of pyridyl ring B and imidazole ring D is 8.4 (3)°, and that of pyridyl ring C and imidazole ring D is 84.1 (3)°, suggesting that the plane of ring A and B are co-planar with ring D, but that ring C and ring D are almost vertical.

In the crystal lattice the molecules are linked by O—H···N hydrogen bonds, and by weak C—H···N interactions to generate a three-dimensional layer structure (Fig 2).

Experimental

A mixture of 2 g (0.018 mol) of 4-pyridinecarbaldehyde and 8 g (0.1 mol) of ammonium acetate was heated to 393 K with stirring 3 h. The reaction mixture was cooled, the precipitate was filtered off, washed with water, 5% solution of NaOH, and recrystallized from ethanol. Single crystals of 2,4,5-tri(4-pyridyl)imidazole suitable for X-ray analysis were obtained by slow evaporation at room temperature of a methanol solution. ¹H NMR (500 MHz, DMSO-d₆) 8.70(t, 4H), 8.54 (s, 2H), 8.02 (s, 2H), 7.53 (s, 4H) MS: found [M₊] = 299.1, cal [M₊] = 299.3.