5-Aminopentan-1-ol

The title compound, C5H13NO, is an aliphatic aminoalcohol with both functional groups residing on terminal C atoms. Apart from the hydroxy group, all non-H atoms are nearly co-planar, the maximum deviation of an atom taking part in the least-squares plane defined by the mentioned non-H atoms being 0.029 (1) Å. In the crystal, O—H⋯N and N—H⋯O hydrogen bonds connect the molecules, forming a three-dimensional network.


Crystal data
Data collection: APEX2 (Bruker, 2010); cell refinement: SAINT (Bruker, 2010); data reduction: SAINT; program(s) used to solve structure: SIR97 (Altomare et al., 1999); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 (Farrugia, 1997) and Mercury (Macrae et al., 2008); software used to prepare material for publication: SHELXL97 and PLATON (Spek, 2009). The possible formation of chelate compounds, in this aspect, is -as a rule of thumb -more likely for smaller chelate ring sizes with four-, five-and six-membered ring systems while the formation of bigger rings is comparatively hampered. As a consequence, the knowledge about the properties of such compounds is limited and precludes a thorough assessment of their properties. In our continuous efforts to elucidate the rules guiding the formation of coordination compounds with chelate ligands featuring a N/O-set of donor atoms, we determined the crystal structure of the title compound to allow for comparative studies with envisioned coordination compounds. The crystal structure of the oxidation product of the title compound, 5-aminovaleric acid, is apparent in the literature (Honda et al., 1990).

Structure Reports Online
The molecule is a primary alcohol and primary amine at the same time. The molecule adopts a zigzag-chain conformation.
Apart from the hydroxy group, all non-hydrogen atoms are in-plane. The OH group encloses a dihedral angle of 62.86 (8)° with the atoms of the carbon chain ( Fig. 1 and Fig. 2).
In the molecule, hydrogen bonds between the hydroxy group as well as the amino groups give rise to a three-dimensional network. While a set of cooperative hydrogen bonds (alternating between hydroxy groups and amino groups) connects the molecules to discrete tetrameric units (Fig. 3), the remaining hydrogen atom of the amino group gives rise to centrosymmetric dimers upon interaction with the hydroxy group. In terms of graph-set analysis (Etter et al., 1990;Bernstein et al., 1995), the hydrogen bonding system requires a C 1 1 (8)C 1 1 (8)C 1 1 (8) descriptor on the unitary level. A description of the cooperative set of hydrogen bonds is possible on the binary level with a R 4 4 (8) descriptor while the centrosymmetric dimers necessitate a R 2 2 (16) descriptor on the unitary level (Fig. 4).
The packing of the compound in the crystal is shown in Figure 5.

Experimental
The compound was obtained commercially (Aldrich). Crystals suitable for the X-ray diffraction study were taken directly from the provided compound.