2,4,5-Tris(pyridin-4-yl)-1H-imidazole monohydrate

Shen-Tang Wang; Guang-Bo Che; Chun-Bo Liu; Xing Wang; Ling Liu

doi:10.1107/S1600536811053013

. 2011 Dec 14;68(Pt 1):o130. doi: 10.1107/S1600536811053013

2,4,5-Tris(pyridin-4-yl)-1H-imidazole monohydrate

Shen-Tang Wang ^a, Guang-Bo Che ^a, Chun-Bo Liu ^a,^*, Xing Wang ^a, Ling Liu ^a

PMCID: PMC3254476 PMID: 22259418

Abstract

In the crystal structure of the title compound, C₁₈H₁₃N₅·H₂O, adjacent molecules are linked by O—H⋯N and N—H⋯O hydrogen bonds, generating a chain propagating along [001].

Related literature

For the use of 2,4,5-tri(4-pyridyl)imidazole in the construction of metal-organic coordination polymers, see: Wang et al. (2009 ▶); Liang et al. (2009 ▶). For related structures, see: Jiang & Hou (2011 ▶); Li (2011 ▶); Li & Xia (2011 ▶). For the preparation, see: Proskurnina et al. (2002 ▶).

Experimental

Crystal data

C₁₈H₁₃N₅·H₂O
M _r = 317.35
Triclinic,
a = 8.1510 (16) Å
b = 9.5210 (19) Å
c = 11.506 (2) Å
α = 103.80 (3)°
β = 105.64 (3)°
γ = 101.03 (3)°
V = 803.3 (4) Å³
Z = 2
Mo Kα radiation
μ = 0.09 mm⁻¹
T = 293 K
0.35 × 0.25 × 0.2 mm

Data collection

Bruker SMART diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2002 ▶) T _min = 0.970, T _max = 1.000
7510 measured reflections
2912 independent reflections
1792 reflections with I > 2σ(I)
R _int = 0.040

Refinement

R[F ² > 2σ(F ²)] = 0.058
wR(F ²) = 0.125
S = 1.02
2876 reflections
218 parameters
H-atom parameters constrained
Δρ_max = 0.19 e Å⁻³
Δρ_min = −0.17 e Å⁻³

Data collection: SMART (Bruker, 2002 ▶); cell refinement: SAINT (Bruker, 2002 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: SHELXTL (Sheldrick, 2008 ▶) and DIAMOND (Brandenburg, 1998 ▶); software used to prepare material for publication: SHELXTL.

Supplementary Material

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S1600536811053013/zj2036sup1.cif

e-68-0o130-sup1.cif^{(19KB, cif)}

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536811053013/zj2036Isup2.hkl

e-68-0o130-Isup2.hkl^{(138.3KB, hkl)}

Supplementary material file. DOI: 10.1107/S1600536811053013/zj2036Isup3.cml

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
O1—H1A⋯N5ⁱ	0.85	1.99	2.843 (3)	177
N1—H1⋯O1	0.89	1.85	2.741 (3)	176
O1—H1B⋯N4ⁱⁱ	0.85	1.94	2.787 (3)	172

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

Acknowledgments

The authors thank Jiangsu University for supporting this work.

supplementary crystallographic information

Comment

In the 2,4,5-tri(4-pyridyl)imidazole three pyridyl groups (pyridyl ring B (C4-C8 and N3), C (C9-C13 and N4), D (C14-C18 and N5)) are directly connected with the imidazole ring A (C1-C3 , N1 and N2). The dihedral angles between the mean planes of pyridyl ring B and imidazole ring A, pyridyl ring C and imidazole ring A, and pyridyl ring D and imidazole ring A are 9.1 (7) °, 21.5 (5) °, 45.5 (1) °, respectively.

We report herein on the crystal structure of the title compound (Fig. 1). In the crystal lattice the molecules are linked by O—H···N and N—H···O hydrogen bonds (Jiang et al. 2011; Li et al. 2011; Li 2011) interactions to generate a one-dimensional double chain structure (Fig. 2).

Experimental

The 2,4,5-tri(4-pyridyl)imidazole was prepared by the methord reported in the literature (Proskurnina et al. 2002). A mixture of 2,4,5-tri(4-pyridyl)imidazole (0.030 g, 0.1 mmol), 2 drops of 1 mol/L HCl and water (10 mL) was placed in a 25 mL Teflon-lined autoclave and heated for 3 d at 433 K under autogenous pressure. Upon cooling and opening the bomb, colourless block-shaped crystals were obtained, then washed with water and dried in air.