dl-Tyrosinium chloride dihydrate

Abstract

In the title compound, C(9)H(12)NO(3) (+)·Cl(-)·2H(2)O, the cation has a protonated amino group resulting from proton transfer from chloridric acid. The structure displays double layers parallel to the [010] direction held together by N-H⋯O, N-H⋯Cl, O-H⋯O and O-H⋯Cl hydrogen bonds. These layers are stacked along the c axis at b = 1/2; within each layer, the tyrosinium cations are arranged in an alternating head-to-tail sequence, forming inversion dimers [R(2) (2)(10) motif]. The water mol-ecules allow for the construction of a three-dimensional hydrogen-bonded network formed by centrosymmetric R(6) (6)(28) and R(8) (8)(34) motifs.

Fig. 1.

The asymmetric unit of (I) (Fig.1), showing the crystallographic numbering scheme. Displacement ellipsoids are drawn at the 50% probability level and H atoms are shown as spheres of arbitrary radii. Hydrogen bonds are shown as dashed lines.

Fig. 2.

Part of the crystal structures, showing the formation of dimers via N—H···O hydrogen bonds, and the aggregation of R22(10), R24(8) and R35(13) motifs [Symmetry codes: (i) -x + 1, -y + 1, -z + 1; (ii) x + 1, y, z]. For the sake of clarity, the water molecules in (I), and H atoms not involved in hydrogen bonding have been omitted. Only atoms involved in hydrogen bonding are labelled.

Fig. 3.

Packing view of (I) showing the aggregation of R24(8), R66(28) and R88(34) hydrogen-bonding motifs. [Symmetry codes:(i) -x + 1, -y + 1, -z + 1; (iii) -x + 1, -y + 1, -z + 2]. For the sake of clarity, the chloride anions, and H atoms not involved in hydrogen bonding have been omitted. Only atoms involved in hydrogen bonding are labelled.