ISSN:
1600-5759
Source:
Crystallography Journals Online : IUCR Backfile Archive 1948-2001
Topics:
Chemistry and Pharmacology
,
Geosciences
,
Physics
Notes:
The title compounds, C12H13NO4, are derived from L-threonine and DL-threonine, respectively. Hydrogen bonding in the chiral derivative, (2S/3R)-3-hydroxy-2-(1-oxoisoindolin-2-yl)butanoic acid, consists of O—Hacid...Oalkyl—H...O=Cindole chains [O...O 2.659 (3) and 2.718 (3) Å], Csp3—H...O and three C—H...πarene interactions. In the (2R,3S/2S,3R) racemate, conventional carboxylic acid hydrogen bonding as cyclical (O—H...O=C)2 [graph set R22(8)] is present, with Oalkyl—H...O=Cindole, Csp3—H...O and C—H...πarene interactions. The COOH group geometry differs between the two forms, with C—O, C=O, C—C—O and C—C=O bond lengths and angles of 1.322 (3) and 1.193 (3) Å, and 109.7 (2) and 125.4 (3)°, respectively, in the chiral structure, and 1.2961 (17) and 1.2210 (18) Å, and 113.29 (12) and 122.63 (13)°, respectively, in the racemate structure. The O—C=O angles of 124.9 (3) and 124.05 (14)° are similar. The differences arise from the contrasting COOH hydrogen-bonding environments in the two structures.
Type of Medium:
Electronic Resource
URL:
http://dx.doi.org/10.1107/S0108270199015619
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