Crystal structure of rac-3-hydroxy-2-(p-tolyl)-2,3,3a,4,7,7a-hexahydro-1H-4,7-methanoisoindol-1-one

In the title compound, C16H17NO2, the cyclohexene ring adopts a boat conformation, and the five-membered rings have envelope conformations with the bridging atom as the flap. Their mean planes are oriented at a dihedral angle of 86.51 (7)°. The molecular structure is stabilized by a short intramolecular C—H⋯O contact. In the crystal, molecules are linked by O—H⋯O hydrogen bonds forming chains propagating along [100]. The chains are linked by C—H⋯π interactions, forming slabs parallel to (001).

In the crystal, molecules are linked by O-H···O hydrogen bonds forming chains along [100]; see Table 1 and Fig. 2.
The chains are linked by C-H···π interactions forming slabs parallel to (001); see Table 1.

Figure 1
The molecular structure of the title compound, with atom labelling. Displacement ellipsoids are drawn at the 30% probability level.

sup-3
Acta Cryst. (2015). E71, o143-o144  Table 1 for details).  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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å 2 )
x y z U iso */U eq O1 0.45122 (