(2-Aminophenyl)methanol

The crystal strucure of the title compound, C7H9NO, displays N—H⋯O hydrogen bonds which link molecules related by translation along the b axis, and O—H⋯N and further N—H⋯O hydrogen bonds which link molecules related by the 21 screw axis along the c axis. The resulting combination is a hydrogen-bonded layer of molecules parallel to (011).

The crystal strucure of the title compound, C 7 H 9 NO, displays N-HÁ Á ÁO hydrogen bonds which link molecules related by translation along the b axis, and O-HÁ Á ÁN and further N-HÁ Á ÁO hydrogen bonds which link molecules related by the 2 1 screw axis along the c axis. The resulting combination is a hydrogen-bonded layer of molecules parallel to (011).

Related literature
For the use of amines in the pharmaceutical industry, see: Morissette et al. (2004). For the use of amines in crystal engineering, see: Bernstein et al. (1999). For hydrogen-bond motifs, see: Bernstein et al. (1995); Etter et al. (1990).

Structure Reports Online
The title compound (I) is capable of forming hydrogen bonds through the alcohol and amine groups ( Fig. 1). In this structure, molecules related by translation along the b axis are linked by the N1-H1A···O1 hydrogen bond to form a C6 chain (Etter et al., 1990;Bernstein et al., 1995) along the b axis. In addition, molecules related by the 2 fold screw axis along c, are held together by the O1-H1···N1 hydrogen bond and the N1-H1B···O1 to form a chain of molecules which appear as a stack of molecules when viewed down the c axis (Fig. 2). The combination of these two hydrogen bonded chains results in a hydrogen bonded layer of molecules parallel to (011).

Experimental
The title compound was purchased from Sigma Aldrich and was recrystallized from dichloromethane and hexane (1:1) to yield colourless needles.

Refinement
With the exception of those involved in hydrogen bonding, all H atoms were first located in the difference Fourier map and then positioned geometrically, and allowed to ride on their parent atoms. Hydrogen bond lengths were set as follows for C-H = 0.95 Å (CH) or 0.99 Å (CH 2 ). Hydrogen atoms involved in hydrogen bonding (N-H and O-H) were located in the difference Fourier map and then allowed to ride on their parent atoms with unmodified N-H and O-H distances.
Isotropic displacement parameters for the H atoms were set as follows: 1.2 times U eq of the parent atom for C and N, and 1.5 times U eq of the parent atom for O. Though the molecule crystallizes in a polar space group it was not possible to determine the absolute conformation of the crystal. As a consequence all Friedel pairs were merged during the final refinements with a SHELXL97 MERG 4 instruction.
supplementary materials sup-2 Figures   Fig. 1. The molecular structure of (I), showing the atomic numbering scheme. Displacement ellipsoids are drawn at the 50% probability level.