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Volume 69 
Part 2 
Page o189  
February 2013  

Received 17 December 2012
Accepted 23 December 2012
Online 4 January 2013

Key indicators
Single-crystal X-ray study
T = 296 K
Mean [sigma](C-C) = 0.004 Å
R = 0.070
wR = 0.249
Data-to-parameter ratio = 20.3
Details
Open access

2-(2-Hydroxy-2-phenylethyl)-1-methylcyclopropan-1-ol

aCollege of Chemistry and Life Science, Zhejiang Normal University, Jinhua 321004, Zhejiang, People's Republic of China
Correspondence e-mail: maohui2011@zjnu.cn

The asymmetric unit of the title compound, C12H16O2, contains two independent molecules in which the dihedral angles between the benzene and cyclopropane rings are 75.9 (3) and 76.3 (3)°. In the crystal, the molecules are connected by O-H...O hydrogen bonds into a three dimensional supramolecular structure.

Related literature

For applications of cyclopropane derivatives, see: Pietruszka (2003[Pietruszka, J. (2003). Chem. Rev. 103, 1051-1070.]); Helene et al. (2003[Helene, L., Marcoux, J. C., Molinaro, C. & Charette, A. B. (2003). Chem. Rev. 103, 977-1050.]); Wessjohann et al. (2003[Wessjohann, L. A., Brandt, W. & Thiemann, T. (2003). Chem. Rev. 103, 1625-1648.]); Charette & Marcoux (1995[Charette, A. B. & Marcoux, J. C. (1995). Synlett, 12, 1197-1207.]).

[Scheme 1]

Experimental

Crystal data
  • C12H16O2

  • Mr = 192.25

  • Triclinic, [P \overline 1]

  • a = 9.1700 (8) Å

  • b = 10.3863 (10) Å

  • c = 11.9412 (11) Å

  • [alpha] = 98.133 (7)°

  • [beta] = 90.854 (6)°

  • [gamma] = 91.841 (7)°

  • V = 1125.07 (18) Å3

  • Z = 4

  • Mo K[alpha] radiation

  • [mu] = 0.08 mm-1

  • T = 296 K

  • 0.13 × 0.10 × 0.08 mm

Data collection
  • Bruker SMART APEXII area-detector diffractometer

  • 16925 measured reflections

  • 5146 independent reflections

  • 2391 reflections with I > 2[sigma](I)

  • Rint = 0.038

Refinement
  • R[F2 > 2[sigma](F2)] = 0.070

  • wR(F2) = 0.249

  • S = 1.04

  • 5146 reflections

  • 253 parameters

  • 4 restraints

  • H-atom parameters constrained

  • [Delta][rho]max = 0.37 e Å-3

  • [Delta][rho]min = -0.39 e Å-3

Table 1
Hydrogen-bond geometry (Å, °)

D-H...A D-H H...A D...A D-H...A
O1-H1A...O2i 0.82 1.94 2.745 (2) 167
O1A-H1AA...O2Aii 0.82 1.95 2.757 (2) 167
O2-H2B...O1A 0.82 1.96 2.768 (3) 167
O2A-H2AB...O1iii 0.82 1.98 2.778 (2) 165
Symmetry codes: (i) -x, -y+1, -z; (ii) -x+1, -y+1, -z+1; (iii) x, y, z+1.

Data collection: APEX2 (Bruker, 2006[Bruker (2006). SAINT and APEX2. Bruker AXS Inc., Madison, Wisconsin, USA.]); cell refinement: SAINT (Bruker, 2006[Bruker (2006). SAINT and APEX2. Bruker AXS Inc., Madison, Wisconsin, USA.]); data reduction: SAINT; 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.


Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: XU5667 ).


References

Bruker (2006). SAINT and APEX2. Bruker AXS Inc., Madison, Wisconsin, USA.
Charette, A. B. & Marcoux, J. C. (1995). Synlett, 12, 1197-1207.  [CrossRef]
Helene, L., Marcoux, J. C., Molinaro, C. & Charette, A. B. (2003). Chem. Rev. 103, 977-1050.  [ISI] [PubMed]
Pietruszka, J. (2003). Chem. Rev. 103, 1051-1070.  [ISI] [CrossRef] [PubMed] [ChemPort]
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.  [CrossRef] [details]
Wessjohann, L. A., Brandt, W. & Thiemann, T. (2003). Chem. Rev. 103, 1625-1648.  [ISI] [CrossRef] [PubMed] [ChemPort]


Acta Cryst (2013). E69, o189  [ doi:10.1107/S1600536812051768 ]

This is an open-access article distributed under the terms of the Creative Commons Attribution Licence, which permits unrestricted use, distribution, and reproduction in any medium, provided the original authors and source are cited.