Open AccessO—H⋯O, C—H⋯O and C—H⋯π arene intermolecular interactions in (2 S )‐2‐(1‐oxo‐1 H ‐2,3‐dihydroisoindol‐2‐yl)pentanoic acid and (2 S )‐3‐methyl‐2‐(1‐oxo‐1 H ‐2,3‐dihydroisoindol‐2‐yl)butanoic acid
Author(s) -
Brady Fiona,
Gallagher John F.
Publication year - 2000
Publication title -
acta crystallographica section c
Language(s) - English
Resource type - Journals
eISSN - 1600-5759
pISSN - 0108-2701
DOI - 10.1107/s0108270100003553
Subject(s) - intermolecular force , chemistry , hydrogen bond , stereochemistry , derivative (finance) , cooperativity , valine , crystallography , molecule , amino acid , biochemistry , organic chemistry , financial economics , economics
In the first of the title compounds, (2 S )‐2‐(1‐oxo‐1 H ‐2,3‐dihydroisoindol‐2‐yl)pentanoic acid, C 13 H 15 NO 3 , prepared from l ‐norvaline, a hydrogen‐bonded network is formed in the solid state through O—H⋯O=C, C—H⋯O=C and C—H⋯π arene intermolecular interactions, with shortest O⋯O, C⋯O and C⋯centroid distances of 2.582 (13), 3.231 (11) and 3.466 (3) Å, respectively. In the l ‐valine derivative, (2 S )‐3‐methyl‐2‐(1‐oxo‐1 H ‐2,3‐dihydroisoindol‐2‐yl)butanoic acid, C 13 H 15 NO 3 , O—H⋯O=C and C arene —H⋯O=C intermolecular interactions generate a cyclic R (9) motif through cooperativity, with shortest O⋯O and C⋯O distances of 2.634 (3) and 3.529 (5) Å, respectively. Methylene C—H⋯O=C indole interactions complete the hydrogen bonding, with C⋯O distances ranging from 3.283 (4) to 3.477 (4) Å.