Intermolecular interactions in the chiral and racemic forms of 3-hydroxy-2-(1-oxoisoindolin-2-yl)butanoic acid derived from threonine.
نویسندگان
چکیده
The title compounds, C12H13NO4, are derived from lthreonine and dl-threonine, respectively. Hydrogen bonding in the chiral derivative, (2S/3R)-3-hydroxy-2-(1-oxoisoindolin2-yl)butanoic acid, consists of OÐHacid OalkylÐ H O Cindole chains [O O 2.659 (3) and 2.718 (3) AÊ ], CspÐH O and three CÐH arene interactions. In the (2R,3S/2S,3R) racemate, conventional carboxylic acid hydrogen bonding as cyclical (OÐH O C)2 [graph set R2 (8)] is present, with OalkylÐH O Cindole, CspÐH O and CÐH arene interactions. The COOH group geometry differs between the two forms, with CÐO, C O, CÐCÐO and CÐC O bond lengths and angles of 1.322 (3) and 1.193 (3) AÊ , and 109.7 (2) and 125.4 (3) , respectively, in the chiral structure, and 1.2961 (17) and 1.2210 (18) AÊ , and 113.29 (12) and 122.63 (13) , respectively, in the racemate structure. The OÐC 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.
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ورودعنوان ژورنال:
- Acta crystallographica. Section C, Crystal structure communications
دوره 56 ( Pt 3) شماره
صفحات -
تاریخ انتشار 2000