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Crystal structure of isopropyl 2-hy-droxy-2-phenyl-acetate: a pharmacopoeia reference standard.
The title compound, C11H14O3, is used as a pharmacopoeia reference standard for determining impurities in the drug Pregabalin, used for the treatment of epilepsy and diabetic neuropathic pain. The mol-ecule is far from being planar, with the dihedral angle between the planes of the aromatic ring and the carboxyl fragment (O-C=O) being 76.1 (6)°. The isopropyl substituent is located in a synperiplanar position relative to the C=O bond and is turned so that the C-O-C-H torsion angle is -43.7°. In the crystal, bifurcated O-H⋯(O,O) hydrogen bonds, enclosing R1(2)(5) ring motifs, lead to the formation of chains propagating along the c-axis direction. Inversion-related chains are linked by the C-H⋯O hydrogen bonds, forming undulating layers lying parallel to the bc plane.
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