Propyl 4-hydroxy­benzoate

Yiwen Zhou; Guzalnur Matsadiq; Yanling Wu; Jing Xiao; Jing Cheng

doi:10.1107/S1600536810000139

. 2010 Jan 30;66(Pt 2):o485. doi: 10.1107/S1600536810000139

Propyl 4-hydroxybenzoate

Yiwen Zhou ^a, Guzalnur Matsadiq ^a, Yanling Wu ^a, Jing Xiao ^a, Jing Cheng ^a,^*

PMCID: PMC2979756 PMID: 21579892

Abstract

There are two molecules in the asymmetric unit of the title compound, C₁₀H₁₂O₃. In the crystal, molecules are linked by O—H⋯O hydrogen bonds into chains running along [010]. Adjacent chains are joined together by weak π–π interactions between benzene rings [centroid–centroid distance = 4.040 (2) Å].

Related literature

For the structure of another p-hydroxybenzoate, see: Mandal & Kadirvelraj (1996 ▶).

Experimental

Crystal data

C₁₀H₁₂O₃
M _r = 180.20
Monoclinic,
a = 12.0634 (12) Å
b = 13.8419 (14) Å
c = 11.7982 (11) Å
β = 108.625 (2)°
V = 1866.9 (3) Å³
Z = 8
Mo Kα radiation
μ = 0.09 mm⁻¹
T = 298 K
0.30 × 0.20 × 0.20 mm

Data collection

Bruker SMART APEX CCD area-detector diffractometer
10603 measured reflections
3271 independent reflections
2960 reflections with I > 2σ(I)
R _int = 0.027

Refinement

R[F ² > 2σ(F ²)] = 0.083
wR(F ²) = 0.189
S = 1.27
3271 reflections
237 parameters
H-atom parameters constrained
Δρ_max = 0.24 e Å⁻³
Δρ_min = −0.30 e Å⁻³

Data collection: SMART (Bruker, 2001 ▶); cell refinement: SAINT-Plus (Bruker, 2001 ▶); data reduction: SAINT-Plus; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: PLATON (Spek, 2009 ▶); software used to prepare material for publication: PLATON.

Supplementary Material

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536810000139/fk2009sup1.cif

e-66-0o485-sup1.cif^{(18.8KB, cif)}

Structure factors: contains datablocks I. DOI: 10.1107/S1600536810000139/fk2009Isup2.hkl

e-66-0o485-Isup2.hkl^{(160.5KB, 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
O4—H4⋯O5ⁱ	0.82	1.93	2.730 (3)	167
O1—H1⋯O2ⁱⁱ	0.82	1.91	2.720 (3)	171

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

Acknowledgments

We would like to thank the National Nature Science Foundation of China (30971948) and Wuhan’s program in science and technology (200760423155) for financial support for this work. We also wish to express our thanks to Meng Xianggao for his warmest help and patience.

supplementary crystallographic information

Comment

The propyl 4-hydroxybenzoate is a kind of p-hydroxybenzoates, which are also known as Nipagin esters. Nipagin ester is a preservative of large consumption in the world. Due to the high antibacterial activity and low toxicity of Nipagin ester, it becomes an inevitable trend that Nipagin ester replaces the traditional preservative. Here, we report the crystal structure of propyl 4-hydroxybenzoate.

There are two molecules in the asymmetric unit (Fig. 1). All bond lengths and bond angles lie in expected ranges.

As shown in Fig.2, molecules are linked by O—H···O hydrogen bonds into one-dimensional chains running along the [010] direction. Adjacent chains are further linked together by weak π–π interactions between two phenyl rings (centroid-to-centroid distance is 4.040 Å).

Experimental

¹H-NMR (C₃D₆O,600MHZ):δ7.916(d,2H,aromatic),δ6.933(d,2H,aromatic), δ4.208(t,2H,-COOCH₂-),δ2.096(s,1H,-OH),δ1.752(q,2H,-CH₂-), δ1.004(t,3H,-CH₃);

Crystals appropriate for data collection were obtained by slow evaporation of an ethanol solution at room temperature.