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The structures of the D-3-phosphoglycerate trianion in the tris{[tris(2-hydroxymethyl)methyl]ammonium} salt, 3C4H12NO3+.C3H4O7P3−, (I), and in the tris(cyclohexylammonium) ethanol solvate 3C6H14N+.C3H4O7P3−.C2H5OH, (II), has been determined by X-ray analyses at 150 and 85 K, respectively. A notable feature of (I) is the shortest P—O(ester) bond [1.607 (2) Å] found so far for the completely ionized phosphate ester group. In contrast, in (II) this bond length is 1.627 (2) Å, similar to that observed in other doubly ionized phosphate ester groups. In (II) the carboxyl­ate group is twisted by −23.5 (4)° relative to the α-hydroxyl group, as indicated by the O1—C1—C2—O2 torsion angle, whereas in (I), the O2—C2—C1—O1 system is almost planar. Both crystal structures are stabilized by hydrogen bonds utilizing all N and O atoms.

Supporting information

cif

Crystallographic Information File (CIF)
Contains datablocks 1, 2, default

fcf

Structure factor file (CIF format)
Contains datablock 2

hkl

Structure factor file (CIF format)
Contains datablock 1

CCDC references: 130747; 130748

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