Desvenlafaxinium chloranilate ethyl acetate solvate

Abstract

In the cation of the title compound, C16H26NO2 (+)·C6HCl2O4 (-)·C4H8O2, the 1-hy-droxy-cyclo-hexyl ring adopts a slightly distorted chair conformation. The dihedral angle between the mean planes of the 1-hy-droxy-cyclo-hexyl and 4-hy-droxy-phenyl rings is 84.0 (8)°. In the anion, the hydroxyl H atom is twisted slightly out of the ring plane with a C-C-O-H torsion angle of -171.9°. Disorder was modeled for the methyl group of the acetate group in the solvate with an occupancy ratio of 0.583 (15): 0.417 (15). In the crystal, O-H⋯O hydrogen bonds are observed between cations and between cations and anions, while bifuricated N-H⋯(O,O) cation-anion hydrogen bonds are also present, forming chains along [010] and [100]. In addition weak cation-anion and cation-solvate C-H⋯O inter-actions occur.

Fig. 1.

ORTEP drawings of cation (C16H26NO2+), anion (C6HCl2O4-), solvate (C4H8O2), in the asymmetric unit of (I) showing the atom labeling scheme and 30% probability displacement ellipsoids. Dashed lines indicate N—H···O, O—H···O hydrogen bonds and weak C—H···O intermolecular interactions. Only the major component of the disordered solvent methyl group is shown.

Fig. 2.

Molecular packing for (I) viewed along the c axis. Dashed lines indicate hydrogen bonds between cation (C16H26NO2+), anion (C6HCl2O4-) and solvate (C4H8O2) groups forming chains along [0 1 0] and [1 0 0]. Weak C—H···O cation-anion and cation-solvate intermolecular interactions also influence crystal packing. Only the major component of the disordered solvent methyl group is shown.