2-Hy­droxy­ethyl 4-hy­droxy­benzoate

M Jeyalaxmi; G Jagadeesan; J Arulmoli; D Roop Singh; S Aravindhan

doi:10.1107/S1600536810054516

. 2011 Jan 22;67(Pt 2):o442. doi: 10.1107/S1600536810054516

2-Hydroxyethyl 4-hydroxybenzoate

M Jeyalaxmi ^a, G Jagadeesan ^a, J Arulmoli ^b, D Roop Singh ^b, S Aravindhan ^a,^*

PMCID: PMC3051633 PMID: 21523106

Abstract

In the title compound, C₉H₁₀O₄, the dihedral angle between the benzene ring and the –CO₂ unit is 11.93 (8)° and the conformation of the 2-hydroxyethyl side chain is gauche [O—C—C—O = −71.91 (17)°]. In the crystal, molecules are linked by O—H⋯O and C—H⋯O hydrogen bonds.

Related literature

For background to the properties of esters of 4-hydroxybenzoic acid, see: Kadokawa et al. (2002 ▶).

Experimental

Crystal data

C₉H₁₀O₄
M _r = 182.17
Triclinic,
a = 4.4235 (10) Å
b = 5.6850 (17) Å
c = 8.7050 (17) Å
α = 80.819 (13)°
β = 79.943 (14)°
γ = 81.804 (14)°
V = 211.30 (9) Å³
Z = 1
Mo Kα radiation
μ = 0.11 mm⁻¹
T = 293 K
0.20 × 0.20 × 0.20 mm

Data collection

Bruker SMART APEXII CCD diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2008 ▶) T _min = 0.978, T _max = 0.982
3761 measured reflections
1767 independent reflections
1609 reflections with I > 2σ(I)
R _int = 0.018

Refinement

R[F ² > 2σ(F ²)] = 0.031
wR(F ²) = 0.088
S = 1.06
1767 reflections
126 parameters
3 restraints
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.21 e Å⁻³
Δρ_min = −0.14 e Å⁻³

Data collection: APEX2 (Bruker, 2008 ▶); cell refinement: SAINT (Bruker, 2008 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: ORTEP-3 (Farrugia, 1997 ▶); software used to prepare material for publication: SHELXL97 and PLATON (Spek, 2009 ▶).

Supplementary Material

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536810054516/hb5779sup1.cif

e-67-0o442-sup1.cif^{(14.8KB, cif)}

Structure factors: contains datablocks I. DOI: 10.1107/S1600536810054516/hb5779Isup2.hkl

e-67-0o442-Isup2.hkl^{(85.2KB, 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—H1A⋯O4ⁱ	0.86 (3)	1.87 (3)	2.7204 (19)	169 (2)
O4—H4A⋯O2ⁱⁱ	0.75 (3)	2.15 (3)	2.8970 (18)	170 (3)
C9—H9A⋯O2ⁱⁱⁱ	0.97	2.51	3.322 (2)	141

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

Acknowledgments

SA thanks the UGC, India, for financial support.

supplementary crystallographic information

Comment

The ORTEP diagram of the title compound, (I), shown in Fig.1 indicates that the aromatic ring is in a plane and the ester group attached to it maintains near planarity with it which is defined by the torsion angles C5—C6—C7—O2 (166.91°), C5—C6—C7—O3 (-12.81°).

Though the C6—C7 is a single bond (1.468 Å) and the possibility of free rotation is high at that connectivity, the planarity exerted by the ester group may be purely because of crystal packing.

The torsion angle O3—C8—C9—O4 is -71.09° which makes the ethyl hydroxy O4 to assume the syn-clinal conformation with respect to the carboxy O3. Such a conformation instead of anti conformation may be due to crystal packing of the molecules which makes them compactly stacked to one another.

The crystal packing (Fig.2) shows the presence of inter-molecular hydrogen bonding. The phenolic oxygen (O1) forms a strong intermolecular hydrogen bond (O1—H1A···O4) with the D···A distance of 2.720 Å and the D—H···A angle of 169°. The ethanolic O4 donates the hydrogen to symmetrically related carbonyl O2 to form intermolecular hydrogen bond (O4—H4A···O2) with the D···A distance of 2.897 Å and the D—H···A angle of 170°. The carbon (C9) atom forms a weak intermolecular hydrogen bond (C9—H9A···O2) with the D···A distance of 3.392 Å and the D—H···A angle is 140.8°. All these three hydrogen bonds are exisiting between a given molecule and three different symmetry related molecules (x - 1, +y + 1, +z - 1 x, +y - 1, +z and x + 1, +y - 1, +z respectively). This multiple hydrogen bonding network makes the well defined crystal packing.

Experimental

An ethanolic solution of 3-methyl-1-phenyl-4-acetylpyrazolin-5-ol (0.432 g, 2 mmol) and 2-aminoethanol (0.122 g, 2mmoL) were taken in a round bottom flask and refluxed for 4 h. The solid product was filtered and washed with cold ethanol. The product obtained was pure by TLC and NMR spectroscopy. However, the product was further purified by re-crystallization from ethanol and dried under vacuum. The compound was crystallized by slow evaporation technique using methanol as solvent at room temperature to yield colourless blocks of (I).