Naphthalen-1-ylmethanol

The molecules of naphthalen-1-ylmethanol are linked by O—H⋯O hydrogen bonds, generating infinite chains propagating parallel to the [100] direction.


Structure description
The title compound, C 11 H 10 O, was first prepared by reduction of the corresponding naphthylamide (West, 1920) and by Grignard reaction involving formaldehyde (Ziegler, 1921). It is available commercially.
The title compound ( Fig. 1) exhibits standard bond lengths and angles. Apart from the OH group, the molecule is almost planar: all carbon atoms are located within 0.03 Å of their mean plane and all aromatic hydrogen atoms are also within 0.04 Å of the same plane. Atom O1 is displaced from the mean plane of the other non-hydrogen atoms (r.m.s. deviation = 0.029 Å ) by À1.260 (1) Å .
In the crystal, the 1-naphthalenemethanol molecules are linked by O1-H1Á Á ÁO1 i hydrogen bonds (Table 1, Fig. 2), generating infinite C(2) chains propagating parallel to the [100] direction: adjacent molecules in a chain are related by a-glide symmetry. Similar chains were observed in 1-naphthaleneethanol (Garozzo & Nazarenko, 2016). Additional C-HÁ Á ÁC(ar) contacts involving the H4 hydrogen atom and C5 and C4 carbon atoms of another chain help to assemble the chains into a weakly bound layer lying parallel to the (010) plane (Fig. 2). These layers are held together by van der Waals forces, forming a molecular crystal.
Difference electron density maps (Fig. 3) show visible positive density at all covalent bonds and at the lone pair area of the oxygen atom. This effect comes from the limitations of the independent atom model; it results, among other shortcomings, in inflated R values and uncertainties of bonding parameters. Application of the Hirshfeld atom refinement data reports with HARt (Fugel et al., 2018) to the same dataset yields a lower R(F) of 0.036 and significantly lower uncertainties for the bond lengths and angles.

Synthesis and crystallization
The title compound is commercially available from Aldrich. Recrystallization from ethanol solution yields needle-like crystals, which were used in the current study.

Refinement
Crystal data, data collection and structure refinement details are summarized in Table 2 Acknowledgements Financial support from the State University of New York for acquisition and maintenance of the X-ray diffractometer is gratefully acknowledged.

Figure 3
Difference map in the plane of the naphthalene ring system (left lower corner: lone pair area of hydroxyl group).

Figure 2
Packing of 1-naphthalenemethanol molecules viewed along the [010] vector. Hydrogen bonds are red, contacts shorter than sum of van der Waals radii are blue. Highlighted hydrogen atoms: H1 (pale blue), H4 (yellow), H8 (green).   where P = (F o 2 + 2F c 2 )/3 (Δ/σ) max < 0.001 Δρ max = 0.35 e Å −3 Δρ min = −0.14 e Å −3 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.