N-[2-(2-Chlorophenyl)-2-hydroxyethyl]propan-2-aminium chloride

In the title compound, C11H17ClNO+·Cl−, the side chain of the ethylamine group is orientated approximately perpendicular to the benzene ring, the dihedral angle between the C/C/N plane of the ethylamine group and the benzene plane being 83.5 (3)°. In the crystal structure, intermolecular O—H⋯Cl and N—H⋯Cl hydrogen bonds are observed. The crystal studied was an inversion twin with a 0.51 (10):0.49 (10) domain ratio.

In the title compound, C 11 H 17 ClNO + ÁCl À , the side chain of the ethylamine group is orientated approximately perpendicular to the benzene ring, the dihedral angle between the C/C/N plane of the ethylamine group and the benzene plane being 83.5 (3) . In the crystal structure, intermolecular O-HÁ Á ÁCl and N-HÁ Á ÁCl hydrogen bonds are observed. The crystal studied was an inversion twin with a 0.51 (10):0.49 (10) domain ratio.
In the molecular structure ( Fig. 1), there are no unusual bond distances or angles. The Cl atom and the phenyl plane is almost planar with the deviation of 0.0037 Å. The dihedral angle between the plane formed by C7/C8/N1 and the phenyl plane is 83.5 (3)°, which shows that the two planes are almost perpendicular. The C9-N1 distance of 1.506 Å is longer than the value of the similar bond distance of 1.474 Å (Tang et al., 2009).
O-H···Cl and N-H···Cl hydrogen bonds are found in the crystal structure and are essential forces in crystal formation.
The hydroxyl hydrogen at O1 acts as a donor to Cl2. The ethylamine hydrogens at N1 also act as donors to Cl2.
ShangHai, China. Racemic Clorprenaline hydrochloride (5 g) was dissolved in ethanol (75 ml) and then hydrochloric acid was added to give pH of about 4. Colorless crystal of (I) separated from the solution in about 80% yield after 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.