Crystal structure of O-benzyl-l-tyrosine N-carb-oxy anhydride

Abstract

In the title compound, C₁₇H₁₅NO₄ (alternative name; O-benzyl-l-tyrosine N-carb-oxy anhydride), the oxazolidine ring is planer, with an r.m.s. deviation of 0.039 Å. The benz-yloxy and benzyl rings are almost coplanar, making a dihedral angle of 0.078 (10)°, and are inclined to the oxazolidine ring by 59.16 (11) and 58.42 (11)°, respectively. In the crystal, mol-ecules are linked by N-H⋯O and C-H⋯O hydrogen bonds, forming ribbons propagating along [010]. The ribbons are linked by C-H⋯π inter-actions, forming a three-dimensional supra-molecular structure. The oxazolidine rings of adjacent ribbons are arranged into a layer parallel to the ab plane. This arrangement is favourable for the polymerization of the compound in the solid state.

Keywords: C—H⋯π inter­actions; O-benzyl-l-tyrosine NCA; crystal structure; hydrogen bonding; l-amino acid N-carb­oxy anhydride; l-tyrosine; solid-state polymerization.

Figure 1

The mol­ecular structure of the title compound, showing the atom labelling and 50% probability displacement ellipsoids.

Figure 2

A partial view along the a axis of the crystal packing of the title compound. The hydrogen bonds are shown as dashed lines (see Table 1 ▸). For clarity, only H atoms H1 and H3 (grey balls) have been included.

Figure 3

A view along the a axis of the crystal packing of the title compound. The hydrogen bonds and C—H⋯π inter­actions are shown as dashed lines (see Table 1 ▸). For clarity, only H atoms H1 and H3 and H6 (grey balls) have been included.