3-Anilino-1-(isopropylamino)propan-2-ol

The title compound, C12H20N2O, was obtained by the reaction of N-(oxiran-2-ylmethyl)aniline and propan-2-amine. In the crystal, molecules are linked by O—H⋯N and N—H⋯O hydrogen bonds into chains parallel to the b axis.

The title compound, C 12 H 20 N 2 O, was obtained by the reaction of N-(oxiran-2-ylmethyl)aniline and propan-2-amine. In the crystal, molecules are linked by O-HÁ Á ÁN and N-HÁ Á ÁO hydrogen bonds into chains parallel to the b axis.

3-Anilino-1-(isopropylamino)propan-2-ol
Xuehui Hou, Ping Hu and Quanjian Lv Comment Amino alcohols are important structural elements for asymmetric catalysis (Li et al., 2004) as well as in biologically active compounds (Ellison & Gandhi, 2005). In order to develop new applications for amino alcohols and their derivatives, structural modifications of these compounds have been extensively investigated. As a contribution in this field, we report here the crystal structure of the title compound.
The molecular structure of the title compound is shown in Fig. 1. A l l bond lengths and angles are not unexceptional. In the crystal structure ( Fig. 2), intermolecular O-H···N and N-H···O hydrogen bonds (Table 1)

Experimental
To a solution of N-(oxiran-2-ylmethyl)aniline (14.9 g, 0.1 mol) in acetone (200 ml), propan-2-amine (86.7 ml, 1.0 mol) was added. The mixture was stirred at room temperature for 6 h, then it was concentrated under reduced pressure and purified by crystallization from ethyl acetate, giving colourless single crystals of the title compound suitablu for X-ray analysis.

Refinement
The amine and hydroxy H atoms were located in a difference Fourier map and refined freely. All other H atoms were placed geometrically and treated as riding on their parent atoms, with C-H = 0.93-0.96 Å and U iso (H) = 1.2U eq (C) or 1.5U eq (C) for methyl H atoms. In the absence of significant anomalous scattering, 464 Friedel pairs were merged.

Figure 2
Crystal packing of the title compound viewed along the b axis, showing the molecular chains formed by intermolecular hydrogen bonds (dashed lines).

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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å 2 )
x y z U iso */U eq N1 −0.0180 (