2-(4-Hydroxyphenyl)acetamide

In the title mol-ecule, C₈H₉NO₂, which is an isomer of acetamino-phen [<i>N</i>-(4-hy-droxy-phen-yl)acetamide], the acetamide group plane subtends a dihedral angle of 89.95 (5)° with respect to the phenyl ring plane with the -NH₂ group directed outward, in contrast to an <i>in vacuo</i> DFT geometry optimization in which the -NH₂ group is directed inward. In the extended structure, N-H⋯O hydrogen bonds organize mol-ecules into stacks propagating along [100], with additional hydrogen bonding linking neighboring parallel stacks. A survey of known structures indicates that the structures of 2-phenyl-acetamide mol-ecules with any substitution at the 4-position on the phenyl ring can demonstrate different orientations for the acetamide group ranging from the -NH₂ group directed almost completely outward to the -NH₂ group directed almost completely inward.