4-[4,5-Bis(pyridin-2-yl)-1H-imidazol-2-yl]phenol monohydrate

Guo-Yong Xiao; Hai-Jun Chi; Peng Lei; Jiang-Long Yu; Zhi-Zhi Hu

doi:10.1107/S1600536810052062

. 2010 Dec 18;67(Pt 1):o161. doi: 10.1107/S1600536810052062

4-[4,5-Bis(pyridin-2-yl)-1H-imidazol-2-yl]phenol monohydrate

Guo-Yong Xiao ^a, Hai-Jun Chi ^a, Peng Lei ^a, Jiang-Long Yu ^b, Zhi-Zhi Hu ^a,^*

PMCID: PMC3050325 PMID: 21522668

Abstract

In the title hydrate, C₁₉H₁₄N₄O·H₂O, the dihedral angle between the two pyridine rings is 38.0 (2)°. The dihedral angle between the imidazole and benzene rings is 25.3 (2)°. The crystal structure is stabilized by intermolecular O—H⋯O, O—H⋯N and N—H⋯O hydrogen bonds.

Related literature

For early studies of lophine (2,4,5-triphenylimidazole), see: Radziszewsky (1877 ▶). For further synthetic details, see: Nakashima et al. (1995 ▶); Kuroda et al. (1993 ▶).

Experimental

Crystal data

C₁₉H₁₄N₄O·H₂O
M _r = 332.36
Triclinic,
a = 8.5875 (17) Å
b = 9.0151 (18) Å
c = 11.353 (2) Å
α = 77.89 (3)°
β = 69.96 (3)°
γ = 73.66 (3)°
V = 786.0 (3) Å³
Z = 2
Mo Kα radiation
μ = 0.10 mm⁻¹
T = 113 K
0.22 × 0.20 × 0.16 mm

Data collection

Bruker SMART CCD diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 1998 ▶) T _min = 0.980, T _max = 0.985
5731 measured reflections
2746 independent reflections
2155 reflections with I > 2σ(I)
R _int = 0.027

Refinement

R[F ² > 2σ(F ²)] = 0.038
wR(F ²) = 0.109
S = 1.09
2746 reflections
239 parameters
4 restraints
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.20 e Å⁻³
Δρ_min = −0.25 e Å⁻³

Data collection: SMART (Bruker, 1998 ▶); cell refinement: SAINT (Bruker, 1998 ▶); 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 ▶); software used to prepare material for publication: SHELXTL.

Supplementary Material

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536810052062/hb5769sup1.cif

e-67-0o161-sup1.cif^{(20KB, cif)}

Structure factors: contains datablocks I. DOI: 10.1107/S1600536810052062/hb5769Isup2.hkl

e-67-0o161-Isup2.hkl^{(134.8KB, 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
O1—H1⋯O2ⁱ	0.82	1.89	2.7003 (17)	171
O2—H2A⋯N3ⁱⁱ	0.88 (1)	1.91 (1)	2.7655 (16)	167 (2)
N2—H2C⋯O2ⁱⁱ	0.91 (1)	2.09 (1)	2.9715 (19)	164 (2)
O2—H2B⋯N4ⁱⁱⁱ	0.87 (1)	1.99 (1)	2.8254 (17)	162 (2)

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

supplementary crystallographic information

Comment

Lophine, 2,4,5-triphenylimidazole, is a well known potential chemiluminesscent (CL) compound (Radziszewsky, 1877). 2-(4-Hydroxyphenyl)-4,5-di(2-pyridyl)imidazole was synthesized by the methods similar to those previously reported (Nakashima et al., 1995; Kuroda et al., 1993). Recently, we have synthesized an analogic structure of imidazole derivative, namely, the title compound, 2-(4-hydroxyphenyl)-4,5-di(2-pyridyl)imidazole. We present its crystal structure here.

The compound consists of a 2-(4-hydroxyphenyl)-4,5-di(2-pyridyl)imidazole molecule and a water molecule of crystallization (Fig. 1). The central imidazole ring forms dihedral angles of 25.3 (2), 22.5 (2), and 29.2 (2)°, respectively, with the C1—C6 benzene ring, C9—C13/N3 pyridine ring, and C15—C19/N4 pyridine ring. The dihedral angle between the two pyridine rings is 38.0 (2)°. The dihedral angle between the central imidazole ring and the benzene ring is 25.3 (2)°. The crystal structure is stabilized by intermolecular O—H···O, O—H···N, and N—H···O hydrogen bonds (Fig. 2, and Table 1).

Experimental

The title compound was prepared by the reaction of 2, 2'-pyridyl (1.0 mmol), 4-hydroxybenzaldehyde (1.0 mmol) and ammonium acetate (10 mmol) in 8 ml acetic acid refluxed for 6 h. After cooling to room temperature, the mixture was poured into water, the precipitate was filtered off and dried to give the target compound in 20% yield. Colourless prisms of the title compound were grown by slow evaporation of a solution in mathanol.