Effect of pressure on the crystal structure of L-serine-I and the crystal structure of L-serine-II at 5.4 GPa

Stephen A. Moggach, David R. Allan, Carole A. Morrison, Simon Parsons, Lindsay Sawyer

Research output: Contribution to journalArticlepeer-review

106 Citations (Scopus)

Abstract

The crystal structure of L-serine has been determined at room temperature at pressures between 0.3 and 4.8 GPa. The structure of this phase (hereafter termed L-serine-I), which consists of the molecules in their zwitterionic tautomer, is orthorhombic, space group P212121, The least compressible cell dimension (c), corresponds to chains of head-to-tail NH⋯carboxylate hydrogen bonds. The most compressible direction is along b, and the pressure-induced distortion in this direction takes the form of closing up voids in the middle of R-type hydrogen-bonded ring motifs. This occurs by a change in the geometry of hydrogen-bonded chains connecting the hydroxyl groups of the - CH2OH side chains. These hydrogen bonds are the longest conventional hydrogen bonds in the system at ambient pressure, having an O⋯O separation of 2.918 (4) Å and an O⋯O⋯O angle of 148.5 (2)°; at 4.8 GPa these parameters are 2.781 (11) and 158.5 (7)°. Elsewhere in the structure one NH⋯O interaction reaches an N⋯O separation of 2.691 (13) Å at 4.8 GPa. This is amongst the shortest of this type of interaction to have been observed in an amino acid crystal structure. Above 4.8 GPa the structure undergoes a single-crystal-to-single-crystal phase transition to a hitherto uncharacterized polymorph, which we designate L-serine-II. The OH⋯OH hydrogen-bonded chains of L-serine-I are replaced in L-serine-II by shorter OH⋯carboxyl interactions, which have an O⋯O separation of 2.62 (2) Å. This phase transition occurs via a change from a gauche to an anti conformation of the OH group, and a change in the NCαCO torsion angle from -178.1 (2)° at 4.8 GPa to -156.3 (10)° at 5.4 GPa. Thus, the same topology appears in both crystal forms, which explains why it occurs from one single-crystal form to another. The transition to L-serine-II is also characterized by the closing-up of voids which occur in the centres of other R-type motifs elsewhere in the structure. There is a marked increase in CH⋯O hydrogen bonding in both phases relative to L-serine-I at ambient pressure.

Original languageEnglish
Pages (from-to)58-68
Number of pages11
JournalActa Crystallographica Section B: Structural Science
Volume61
Issue number1
DOIs
Publication statusPublished - 1 Feb 2005

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