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

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.

The asymmetric unit of the title compound, C 12 H 16 O 2 , 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-HÁ Á ÁO hydrogen bonds into a three dimensional supramolecular structure.
Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: XU5667).
X-ray crystallography confirmed the molecular structure and the atom connectivity for the title compound(I), as illustrated in Fig. 1. A view on the crystal structure of the title compound, the angle of (C9-C10-C11) is 60.8 (2)°, and the angle of (C10-C9-C11) is 59.4 (2)°, and the angle of (C9-C11-C10) is 59.8 (2)°. It can be speculated that the structure of the three ring was similar equilateral triangle. The dihedral angle between the benzene ring and the cyclopropane ring is 75.9 (3) and 76.3 (3)°. The structure is more stable by intramolecular hydrogen bond (O2-H2B···O1A).

Experimental
To a two-necked flask containing samarium powder (2.5 mmol), was added THF (18 ml) and ally bromide (2.2 mmol) under nitrogen. The mixture was allowed to stir at room temperature for 1 h (the color would turn into purple). HMPA (2.0 ml) and H 2 O (1.0 mmol) was then added in sequence via a syringe. A solution of 4-Acetoxy-4-phenyl-1-butene (1.0 mmol) in THF (5.0 ml) was subsequently added. The color would fade out in 3 h (monitored by TLC). After treatment, afford the solid products. Recrystallization condition: Petrol/EtOAc (5/1, v:v), room temperature, one day.

Special details
Geometry. All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell e.s.d.'s are taken into account individually in the estimation of e.s.d.'s in distances, angles and torsion angles; correlations between e.s.d.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell e.s.d.'s is used for estimating e.s.d.'s involving l.s. planes. Refinement. Refinement of F 2 against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F 2 , conventional R-factors R are based on F, with F set to zero for negative F 2 . The threshold expression of F 2 > σ(F 2 ) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F 2 are statistically about twice as large as those based on F, and R-factors based on ALL data will be even larger.