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

Mao, H.; Tu, Y.-W.; Li, S.-K.; Wang, X.-J.; Wang, P.-P.

doi:10.1107/S1600536812051768

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 (C-C) = 0.004 Å
R = 0.070
wR = 0.249
Data-to-parameter ratio = 20.3
Details

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

Hui Mao,^a ^* Ya-Wei Tu,^a Shi-Kun Li,^a Xiao-Juan Wang ^a and Peng-Peng Wang ^a

^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-HO hydrogen bonds into a three dimensional supramolecular structure.

Related literature

For applications of cyclopropane derivatives, see: Pietruszka (2003); Helene et al. (2003); Wessjohann et al. (2003); Charette & Marcoux (1995).

Experimental

Crystal data

C₁₂H₁₆O₂
M_r = 192.25
Triclinic, $[P \overline 1]$
a = 9.1700 (8) Å
b = 10.3863 (10) Å
c = 11.9412 (11) Å
= 98.133 (7)°
= 90.854 (6)°
= 91.841 (7)°
V = 1125.07 (18) Å³
Z = 4
Mo K radiation
= 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(I)
R_int = 0.038

Refinement

R[F² > 2(F²)] = 0.070
wR(F²) = 0.249
S = 1.04
5146 reflections
253 parameters
4 restraints
H-atom parameters constrained
_max = 0.37 e Å^-3
_min = -0.39 e Å^-3

Table 1
Hydrogen-bond geometry (Å, °)

D-HA	D-H	HA	DA	D-HA
O1-H1AO2ⁱ	0.82	1.94	2.745 (2)	167
O1A-H1AAO2Aⁱⁱ	0.82	1.95	2.757 (2)	167
O2-H2BO1A	0.82	1.96	2.768 (3)	167
O2A-H2ABO1ⁱⁱⁱ	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); 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 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.
Helene, L., Marcoux, J. C., Molinaro, C. & Charette, A. B. (2003). Chem. Rev. 103, 977-1050.
Pietruszka, J. (2003). Chem. Rev. 103, 1051-1070.
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.
Wessjohann, L. A., Brandt, W. & Thiemann, T. (2003). Chem. Rev. 103, 1625-1648.

organic compounds