(1R,3S)-3-Hydroxymethyl-N-isopropyl-2,2-dimethylcyclopropanecarboxamide

The asymmetric unit of the title compound, C10H19NO2, prepared from (−)-1R-cis-caronaldehyde, contains two independent molecules. In the crystal structure, intermolecular O—H⋯O and O—H⋯N hydrogen bonds form an extensive three-dimensional hydrogen-bonding network.

The asymmetric unit of the title compound, C 10 H 19 NO 2 , prepared from (À)-1R-cis-caronaldehyde, contains two independent molecules. In the crystal structure, intermolecular O-HÁ Á ÁO and O-HÁ Á ÁN hydrogen bonds form an extensive three-dimensional hydrogen-bonding network.
Financial support from the National Natural Science Foundation of China (grant Nos. 20472111 and 20742004) is gratefully acknowledged.

Comment
In continuation of our study of new (-)-1R-cis-caronaldehyde derivatives (Na & Wang, 2009;Wang et al., 2009), we present here the crystal structure of the title compound (I).
The asymmetric unit of (I) contains two independent molecules (Fig. 1). The crystal structure is stabilized by intermolecular O-H···O and O-H···N hydrogen bonds (Table 1).

Experimental
We have synthesized the title compound following the known procedure (Huang et al., 2001).

Refinement
All H atoms were positioned geometrically and treated as riding on their parent atoms, with C-H = 0.98 -1.00 Å, O-H = 0.84 Å, and with U iso (H) = 1.2-1.5U eq of the parent atom. In the absence of any significant anomalous scatterers in the molecule, the 1671 Friedel pairs were merged before the final refinement. Fig. 1. Two independent molecules of (I), with atomic labels and 30% probability displacement ellipsoids. Some of H atoms omitted for clarity.

Special details
Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds 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 > 2sigma(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.