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Volume 69 
Part 8 
Pages o1303-o1304  
August 2013  

Received 27 June 2013
Accepted 17 July 2013
Online 24 July 2013

Key indicators
Single-crystal X-ray study
T = 123 K
Mean [sigma](C-C) = 0.003 Å
R = 0.051
wR = 0.110
Data-to-parameter ratio = 12.5
Details
Open access

4-(2-Hydroxyethoxy)phenol

aInstitute of Organic Chemistry, Karlsruhe Institute of Technology, Fritz-Haber-Weg 6, 76131 Karlsruhe, Germany,bLaboratory of Inorganic Chemistry, Department of Chemistry, University of Helsinki, PO Box 55, 00014 University of Helsinki, Finland, and cInstitute of Organic Chemistry, Institute of Toxicology and Genetics, Karlsruhe Institute of Technology, Fritz-Haber-Weg 6, 76131 Karlsruhe, Germany
Correspondence e-mail: braese@kit.edu

The asymmetric unit of the title compound, C8H10O3, contains four molecules, which differ in the orientation of the hydroxyethyl group [O-C-C-O torsion angles = -168.89 (17), 72.9 (2), -65.8 (2) and 71.8 (2)°], as well as the orientation of the hydroxy H atoms. Furthermore, the crystal structure displays two different types of strong hydrogen bond. The first is between an alcohol O-H and another alcohol O atom, and the second between an alcohol O-H group and an ether O atom. Additional weak hydrogen bonds between C-H groups and ether O atoms stabilize the structure.

Related literature

For the synthesis of the title compound, see: Read & Miller (1932[Read, R. R. & Miller, E. (1932). J. Am. Chem. Soc. 54, 1195-1199.]). For its biological activity, see: Smit et al. (1992[Smit, N. P. M., Peters, K., Menko, W., Westerhof, W., Pavel, S. & Riley, P. A. (1992). Melanoma Res. 2, 295-304.]). For its use in the synthesis of biologically active materials, see: Ding et al. (2009[Ding, Q., Jiang, N., Yang, S., Zhang, J. & Zhang, Z. (2009). US Patent Appl. Publ. US 20090156610 A1 20090618.]); Pitterna et al. (2004[Pitterna, T., Böger, M. & Maienfisch, P. (2004). Chimia, 58, 108-116.]); Petrovic & Brückner (2011[Petrovic, D. & Brückner, R. (2011). Org. Lett. 13, 6524-6527.]). For its application in polymer synthesis, see: Nakano et al. (2000[Nakano, S., Nakanishi, S., Izumi, K., Yoshioka, M. & Mochizuki, O. (2000). Japanese Patent Kokai Tokkyo Koho JP2000327924A20001128.]); Kaneda et al. (2004[Kaneda, K., Kuriya, Y. & Nashiko, T. (2004). Japanese Patent Kokai Tokkyo Koho JP2004175943A20040624.]); Xi et al. (2010[Xi, H., Ju, S., Chen, Z. & Sun, X. (2010). Chem. Lett. 39, 415-417.]). For its use as a substrate for dye synthesis, see: Kelly (1996[Kelly, S. (1996). European Patent Appl. EP748852A219961218.]). For information about the cuprate, used for synthesis, see: Normant et al. (1980[Normant, J. F., Alexakis, A. & Cahiez, G. (1980). Tetrahedron Lett. 21, 935-938.]). For its reactivity, see: Semmelhack et al. (1985[Semmelhack, M. F., Keller, L., Sato, T., Spiess, E. J. & Wulff, W. (1985). J. Org. Chem. 50, 5566-5574.]).

[Scheme 1]

Experimental

Crystal data
  • C8H10O3

  • Mr = 154.16

  • Triclinic, [P \overline 1]

  • a = 10.0388 (10) Å

  • b = 10.2425 (8) Å

  • c = 15.0692 (11) Å

  • [alpha] = 83.916 (8)°

  • [beta] = 86.470 (9)°

  • [gamma] = 77.124 (8)°

  • V = 1500.8 (2) Å3

  • Z = 8

  • Mo K[alpha] radiation

  • [mu] = 0.10 mm-1

  • T = 123 K

  • 0.16 × 0.08 × 0.04 mm

Data collection
  • Bruker Nonius KappaCCD diffractometer

  • Absorption correction: multi-scan (SADABS; Sheldrick, 2003[Sheldrick, G. M. (2003). SADABS. University of Göttingen, Germany.]) Tmin = 0.910, Tmax = 0.997

  • 17940 measured reflections

  • 5282 independent reflections

  • 3204 reflections with I > 2[sigma](I)

  • Rint = 0.058

Refinement
  • R[F2 > 2[sigma](F2)] = 0.051

  • wR(F2) = 0.110

  • S = 1.02

  • 5282 reflections

  • 421 parameters

  • 48 restraints

  • H atoms treated by a mixture of independent and constrained refinement

  • [Delta][rho]max = 0.21 e Å-3

  • [Delta][rho]min = -0.27 e Å-3

Table 1
Selected torsion angles (°)

O1A-C2A-C3A-O4A -168.89 (17)
O1B-C2B-C3B-O4B 72.9 (2)
O1C-C2C-C3C-O4C -65.8 (2)
O1D-C2D-C3D-O4D 71.8 (2)

Table 2
Hydrogen-bond geometry (Å, °)

D-H...A D-H H...A D...A D-H...A
O1A-H1A...O1Ci 0.84 (1) 1.85 (1) 2.671 (2) 165 (2)
O8A-H8A...O1Bii 0.84 (1) 1.74 (1) 2.565 (2) 170 (2)
O1B-H1B...O1Diii 0.84 (1) 1.88 (1) 2.707 (2) 168 (2)
O8B-H8B...O1Ai 0.84 (1) 1.79 (1) 2.617 (2) 169 (2)
O1C-H1C...O4D 0.84 (1) 2.12 (1) 2.830 (2) 142 (2)
O8C-H8C...O8Biv 0.84 (1) 1.88 (1) 2.721 (2) 176 (2)
O1D-H1D...O8Ciii 0.84 (1) 2.02 (1) 2.800 (2) 155 (2)
O8D-H8D...O8Av 0.84 (1) 1.88 (1) 2.707 (2) 167 (2)
C2A-H2A1...O4B 0.99 2.48 3.452 (3) 168
C2B-H2B2...O4A 0.99 2.58 3.450 (3) 147
C2C-H2C1...O8Avi 0.99 2.44 3.402 (3) 163
C9B-H9B...O4Avii 0.95 2.54 3.361 (3) 145
C2C-H2C2...O8Dviii 0.99 2.49 3.337 (3) 144
C2D-H2D2...O4C 0.99 2.57 3.478 (3) 152
Symmetry codes: (i) -x+1, -y+1, -z+1; (ii) -x, -y, -z+2; (iii) -x+1, -y, -z+1; (iv) x-1, y, z; (v) x+2, y, z-1; (vi) x+1, y, z-1; (vii) x+1, y, z; (viii) -x+2, -y+1, -z.

Data collection: COLLECT (Nonius, 1999[Nonius (1999). COLLECT. Nonius BV, Delft, The Netherlands.]); cell refinement: EVALCCD (Duisenberg et al., 2003[Duisenberg, A. J. M., Kroon-Batenburg, L. M. J. & Schreurs, A. M. M. (2003). J. Appl. Cryst. 36, 220-229.]); data reduction: EVALCCD; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); molecular graphics: SHELXTL (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); software used to prepare material for publication: SHELXL97 and publCIF (Westrip, 2010[Westrip, S. P. (2010). J. Appl. Cryst. 43, 920-925.]).


Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: MW2112 ).


Acknowledgements

The authors acknowledge the Fonds der Chemischen Industrie and the Deutsche Forschungsgemeinschaft (DFG) (grant No. BR 1750-12-1) for financial support.

References

Ding, Q., Jiang, N., Yang, S., Zhang, J. & Zhang, Z. (2009). US Patent Appl. Publ. US 20090156610 A1 20090618.
Duisenberg, A. J. M., Kroon-Batenburg, L. M. J. & Schreurs, A. M. M. (2003). J. Appl. Cryst. 36, 220-229.  [Web of Science] [CrossRef] [ChemPort] [IUCr Journals]
Kaneda, K., Kuriya, Y. & Nashiko, T. (2004). Japanese Patent Kokai Tokkyo Koho JP2004175943A20040624.
Kelly, S. (1996). European Patent Appl. EP748852A219961218.
Nakano, S., Nakanishi, S., Izumi, K., Yoshioka, M. & Mochizuki, O. (2000). Japanese Patent Kokai Tokkyo Koho JP2000327924A20001128.
Nonius (1999). COLLECT. Nonius BV, Delft, The Netherlands.
Normant, J. F., Alexakis, A. & Cahiez, G. (1980). Tetrahedron Lett. 21, 935-938.  [CrossRef] [ChemPort]
Petrovic, D. & Brückner, R. (2011). Org. Lett. 13, 6524-6527.  [PubMed]
Pitterna, T., Böger, M. & Maienfisch, P. (2004). Chimia, 58, 108-116.  [CrossRef] [ChemPort]
Read, R. R. & Miller, E. (1932). J. Am. Chem. Soc. 54, 1195-1199.  [CrossRef] [ChemPort]
Semmelhack, M. F., Keller, L., Sato, T., Spiess, E. J. & Wulff, W. (1985). J. Org. Chem. 50, 5566-5574.  [CrossRef] [ChemPort]
Sheldrick, G. M. (2003). SADABS. University of Göttingen, Germany.
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.  [CrossRef] [ChemPort] [IUCr Journals]
Smit, N. P. M., Peters, K., Menko, W., Westerhof, W., Pavel, S. & Riley, P. A. (1992). Melanoma Res. 2, 295-304.  [CrossRef] [PubMed] [ChemPort]
Westrip, S. P. (2010). J. Appl. Cryst. 43, 920-925.  [Web of Science] [CrossRef] [ChemPort] [IUCr Journals]
Xi, H., Ju, S., Chen, Z. & Sun, X. (2010). Chem. Lett. 39, 415-417.  [CrossRef] [ChemPort]


Acta Cryst (2013). E69, o1303-o1304   [ doi:10.1107/S1600536813019818 ]

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