4-{[(1S,2R)-2-Hydroxyindan-1-yl]amino}pent-3-en-2-one

In the molecule of the title compound, C14H17NO2, the dihedral angle formed by the mean planes through the indan ring system and the aminopentenone fragment is 83.26 (13)°. An intramolecular N—H⋯O hydrogen bond is observed. In the crystal, molecules are linked into one-dimensional chains extending along the [010] direction via O—H⋯O and C—H⋯O hydrogen bonds.

In the title compound ( Fig. 1), the C8 carbon atom is displaced by 0.594 (2) Å from the mean plane defined by the C1-C7/C9 atoms of the indane ring system. The dihedral angle formed by the mean planes through the indane ring system and the approximately planar aminopentenone fragment [maximum deviation 0.063 (3) Å for atom C14] is 86.23 (13)°.
The molecular conformation is stabilized by an intramolecular N-H···O hydrogen bond (Table 1). In the crystal structure ( Fig. 2), molecules interact via intermolecular O-H···O and C-H···O hydrogen bonds to generate one-dimensional chains extending along the [0 1 0] direction.

Experimental
A mixture of (1S,2R)-(-)-amino-2-indanol(0.149 g,1 mmol) and 2,4-pentanedione(0.100 g,1 mmol) was stirred in ethanol for 24 h in the presence of catalytic amount of p-toluene sulfonic acid. The residue, obtained by removing the solvent under vacuum, was recrystallized in hexane. The desired product was isolated as white crystals after the solution remained at -20 °C in a refrigerator for a few days (yield 80%, 0.183 g).

Refinement
In the absence of significant anomalous scattering effects, 1121 Friedel pairs were merged in the last cycles of refinement. The absolute configuration was assigned on the basis of the known configuration of the indanyl alcohol employed in the synthesis. The C-bound H-atoms were included in calculated positions and treated as riding atoms, with C-H = 0.93-0.97 Å, and with U iso (H) = 1.2 U eq (C) or 1.5 U eq (C) for methyl H atoms. The amine and hydroxy H atoms were located in a difference Fourier map and refined isotropically.  The molecular structure of the title compound, with displacement ellipsoids drawn at the 50% probability level. H atoms are shown as spheres of arbitrary radius.

Figure 2
The one-dimensional chain structure extending along [010], with hydrogen bonds shown dotted lines. Displacement ellipsoids are drawn at the 50% probability level.

4-{[(1S,2R)-2-Hydroxyindan-1-yl]amino}pent-3-en-2-one
Crystal data C 14 H 17 NO 2 M r = 231.29 Orthorhombic, P2 1 2 1 2 1 Hall symbol: P 2ac 2ab a = 8.3472 (5)  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.