6-(3,5-Dimeth-oxy-benzyl-amino)-9-(oxan-2-yl)-9H-purine

Abstract

The mol-ecule of the title compound, C19H23N5O3, contains six-membered pyrimidine and five-membered imidazole rings merged into the essentially planar purine skeleton (r.m.s. deviation = 0.01 Å). In the crystal, pairs of N-H⋯N hydrogen bonds link mol-ecules into inversion dimers. The dimers are linked via C-H⋯O hydrogen bonds, forming double-stranded chains propagating along [001]. These chains are linked via C-H⋯π and parallel slipped π-π inter-actions [centroid-centroid distance = 3.467 (1) Å; slippage 0.519 Å], forming a three-dimensional network.

Fig. 1.

The molecular structure of the title compound with the non-hydrogen atoms depicted as thermal ellipsoids at the 50% probability level and given with the atom numbering scheme.

Fig. 2.

The model of the title compound, showing the mutual orientation of the six-membered pyrimidine (least-squares plane created through the N1, C2, N3, C4, C5 and C6 atoms; in blue) and five-membered imidazole rings (least-squares plane created through the C4, C5, N7, C8 and N9 atoms; in red). The planes are nearly coplanar forming the dihedral angle of 1.50 (6)°.

Fig. 3.

The model of the title compound, showing the mutual orientation of the purine skeleton (least-squares plane created through the N1, C2, N3, C4, C5, C6, N7, C8 and N9 atoms; in red) and benzene ring (least-squares plane created through the C10, C11, C12, C13, C14 and C15 atoms; in blue). The planes form the dihedral angle of 63.87 (4)°.

Fig. 4.

Part of the crystal structure of the title compound (Ball-and-stick model), showing the N6—H6···N7 hydrogen bonds (dashed green lines; see Table 1 for parameters) and C8—H8···π, C21—H21···π and π···π interactions (dashed orange lines; see Table 1 for C8—H8···Cg and C21—H21···Cg parameters). Cg···Cgiii parameters: d(D···A) = 3.46700 (10) Å. Symmetry codes: (i) –x+2, –y+1, –z+1; (iii) –x+2, –y+2, –z+1; (iv) x, y+1, z.

Fig. 5.

Part of the crystal structure of the title compound (Ball-and-stick model), showing two molecules connected through C16—H16C···N6 non-covalent contacts (dashed orange lines; see Table 1 for parameters). Symmetry code: (v) –x+1, –y+1, –z+1.