2-(4-Hydroxy­phen­yl)acetic acid–4,4′-bipyridine (1/1)

Jian-Feng Liu; Guo-Liang Zhao

doi:10.1107/S1600536810018842

. 2010 May 26;66(Pt 6):o1455. doi: 10.1107/S1600536810018842

2-(4-Hydroxyphenyl)acetic acid–4,4′-bipyridine (1/1)

Jian-Feng Liu ^a, Guo-Liang Zhao ^a,^*

PMCID: PMC2979409 PMID: 21579524

Abstract

In the acid molecule of the title complex, C₁₀H₈N₂·C₈H₈O₃, the acetyl C—C—C—O torsion angle is −32.1 (3)°, and in the molecule of the base, the dihedral angle between the two pyridine rings is 23.41 (10)°. In the crystal structure, intermolecular O—H⋯N hydrogen bonds link the acid and the base molecules into a one-dimensional triple-helix framework extended along the b axis.

Related literature

For related functional complexes, see: Han et al. (2009 ▶). For hydrogen-bond motif structures, see: Tomura & Yamashita (2001 ▶).

Experimental

Crystal data

C₁₀H₈N₂·C₈H₈O₃
M _r = 308.33
Monoclinic,
a = 25.3578 (6) Å
b = 10.2305 (2) Å
c = 14.2546 (4) Å
β = 122.321 (2)°
V = 3125.03 (15) Å³
Z = 8
Mo Kα radiation
μ = 0.09 mm⁻¹
T = 296 K
0.25 × 0.14 × 0.06 mm

Data collection

Bruker APEXII CCD area-detector diffractometer
Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ▶) T _min = 0.984, T _max = 0.994
24334 measured reflections
3650 independent reflections
2128 reflections with I > 2σ(I)
R _int = 0.043

Refinement

R[F ² > 2σ(F ²)] = 0.047
wR(F ²) = 0.139
S = 1.06
3650 reflections
214 parameters
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.15 e Å⁻³
Δρ_min = −0.16 e Å⁻³

Data collection: APEX2 (Bruker, 2006 ▶); cell refinement: SAINT (Bruker, 2006 ▶); 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: SHELXL97.

Supplementary Material

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536810018842/pv2281sup1.cif

e-66-o1455-sup1.cif^{(18.5KB, cif)}

Structure factors: contains datablocks I. DOI: 10.1107/S1600536810018842/pv2281Isup2.hkl

e-66-o1455-Isup2.hkl^{(179.1KB, 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—H2O⋯N2ⁱ	0.97 (2)	1.71 (2)	2.679 (2)	179 (2)
O3—H3O⋯N1ⁱⁱ	0.87 (2)	1.86 (2)	2.728 (2)	171 (2)

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

supplementary crystallographic information

Comment

The design and synthesis of coordination complexes have absorbed considerable attention due to their diverse structures with 4,4'-bipyridine linker (Han et al., 2009). Moreover, hydrogen bond can also play a role in forming motif structures (Tomura & Yamashita, 2001). We have designed the title complex in an attempt to prepare crystaline magnetic materials and report its crystal structure in this paper.

The structure of the title complex is shown in Fig. 1, which reveals that it contains 2-(4-hydroxyphenyl)acetic acid and 4,4'-bipyridine in a ratio of 1:1. In the molecule of 2-(4-hydroxyphenyl)acetic acid, the acetyl torsion angle C(1)—C(7)—C(8)—O(2) is -32.1 (3) °, and in the molecule of 4,4'-bipyridine, the dihedral angle between the two pyridine rings is 23.41 (10) °. The two molecules arranged in the crystal at regular intervals with two O—H···N hydrogen bonds. The end to end hydrogen-bonding interactions lead to the formation of a one-dimensional triple-helix structure framework along the b-axis, Fig 2. Between adjacent triple-helix chains there exist weak π—π interactions.

Experimental

2-(4-hydroxyphenyl)acetic acid (0.152 g, 1 mmol) and 4,4'-bipyridine (0.156 g, 1 mmol) were added to a mixed solution of ethanol (20 ml) and water (10 ml) with Cu(SO₄)₂ (0.127 g, 0.5 mmol) under stirred conditions at room temperature. A few minutes later a lot of blue deposit appeared. After the deposit was filtered out, a light blue solution was kept for evaporating. Colorless single crystals of the title complex were obtained about 19 days later.