2001
DOI: 10.1107/s0108270101004590
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meso-N,N′-Oxalyldivaline

Abstract: The title compound, 2,2'-(oxalyldiimino)bis(3-methylbutanoic acid), C12H20N2O6, possesses a centre of symmetry. In the crystal, molecules are connected by hydrogen bonds between oxamide and carboxyl groups, similar to the pattern of the monoclinic forms of HO-Gly-CO-CO-Gly-OH and HO-Aib-CO-CO-Aib-OH (Gly is glycine and Aib is 2-aminoisobutyric acid). The characteristic torsion angles in the title compound are close to those in peptide alpha-helices.

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Cited by 5 publications
(6 citation statements)
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“…1). The six non-H atoms of the oxamide group are almost coplanar, which is similar to other oxamide compounds (Su et al, 1999;Perić et al, 2001). The C5-C5 i distance [symmetry code: (i) 1 À x, 1 À y, 2 À z] of 1.541 (3) Å is somewhat longer than the analogous bond in the copper complex of the deprotonated parent oxamide [1.518 (5) Å ; Real et al, 1993].…”
Section: Commentsupporting
confidence: 72%
“…1). The six non-H atoms of the oxamide group are almost coplanar, which is similar to other oxamide compounds (Su et al, 1999;Perić et al, 2001). The C5-C5 i distance [symmetry code: (i) 1 À x, 1 À y, 2 À z] of 1.541 (3) Å is somewhat longer than the analogous bond in the copper complex of the deprotonated parent oxamide [1.518 (5) Å ; Real et al, 1993].…”
Section: Commentsupporting
confidence: 72%
“…There is an intramolecular hydrogen bond between amido nitrogen atom (N1) and carboxyl oxygen atom (O2). The zwitterion has a transoid conformation, and six atoms of oxamido group are almost coplanar, which is similar to other oxamido compounds (Perić et al, 2001;Su et al, 1999;Sun et al, 2006). The dihedral angle between the oxamide and the benzene ring is 27.05 (12)°, and that between the benzene ring and carboxyl group is 23.9 (4)°.…”
Section: Sup-1supporting
confidence: 51%
“…For general background, see: Ojima & Nonoyama (1988); Matović et al (2005); Pei et al (1991); Zang et al (2003). For related structures, see: Perić et al (2001); Su et al (1999); Sun et al (2006). For synthesis, see: Matović et al (2005).…”
Section: Related Literaturementioning
confidence: 99%
“…The present structure determination forms part of a systematic study related to hydrogen bonding and gelation properties of bis(amino acid) Peric  et al, 2001) and bis(amino alcohol) oxamide derivatives (Makarevic  et al, 2003). Fig.…”
Section: Commentmentioning
confidence: 99%