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In crystals of O-phospho-DL-threonine and O-phospho-L-threonine, the molecules are zwitterionic HO3POCH(CH3)CH(NH3+)CO2H and linked by three-dimensional networks of strong P-O-H...O=P, C-O-H...O=P, N-H...O=P, and N-H...O=C hydrogen bonds with 〈O...O〉 = 2.55 (3) Å and 〈N...O〉 = 2.84 (4) Å. Both the molecular conformations and the nearest-neighbor hydrogen-bonded surroundings are very similar in the racemic and enantiomeric crystals of the threonine compounds, but earlier studies of crystals of the analogous serine compounds have shown that the serine zwitterions HO3POCH2CH(NH+3)CO2H have different conformations about the Cβ-Oγ-P phosphate ester bonds and different hydrogen-bonded surroundings.

Supporting information

cif

Crystallographic Information File (CIF)
Contains datablocks text, bk1167a, bk1167b

CCDC references: 126904; 126905

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