2-[4-(Piperidin-1-yl)-5H-chromeno[2,3-d]pyrimidin-2-yl]phenol

Abstract

In the title compound, C22H21N3O2, the pyrimidine ring is essentially planar [maximum deviation = 0.018 (2) Å] and forms dihedral angles of 22.70 (8) and 0.97 (7)°, respectively, with the fused benzene ring and the hy-droxy-substituted benzene ring. The piperidine ring has a chair conformation and the pyran ring has a flattened twist-boat conformation. The hy-droxy group was refined as disordered over two sets of sites in a 0.702 (4):0.298 (4) ratio. The disorder corresponds to a rotation of approxomiately 180° about the C-C bond connecting the phenol group to the pyrimidine ring and hence, both the major and minor components of disorder form intra-molecular O-H⋯N hydrogen bonds. In the crystal, pairs of weak C-H⋯π inter-actions form inversion dimers. In addition, π-π inter-actions are observed between the pyrimidine ring and the hy-droxy-substituted benzene ring [centroid-centroid separation = 3.739 (2) Å].

Fig. 1.

The molecular structure of (I) with ellipsoids drawn at the 40% probability level. H atoms are shown as small spheres of arbitrary radii. Both disorder components are shown.

Fig. 2.

Part of the crystal structure with hydrogen bonds shown as dashed lines. Only the H atoms involved in hydrogen bonds and weak C—H···π interactions are shown.