TY - JOUR
T1 - Organic crystal engineering with 1,4-piperazine-2,5-diones. 7. Crystal packing of piperazinediones derived from 2-amino-7-nitro-4-methoxyindan-2- carboxylic acid
AU - Ntirampebura, Deogratias
AU - Jagadish, Bhumasamudram
AU - Nichol, Gary S.
AU - Carducci, Michael D.
AU - Dawson, Alice
AU - Rajapakshe, Asha
AU - Oliver, Allen G.
AU - Clegg, William
AU - Harrington, Ross W.
AU - Layne, Larry
AU - Margolis, Jason I.
AU - Mash, Eugene A.
PY - 2008/9
Y1 - 2008/9
N2 - 1,4-Piperazine-2,5-diones derived from 2-amino-7-nitro-4-methoxyindan-2- carboxylic acid were prepared in meso, racemic, and enantiomerically pure forms, crystallized from DMSO or DMF, and the supramolecular organization in the crystals determined by X-ray crystallography. These molecules were designed to bear two strongly dipolar p-nitroanisole groups, aligned in the enantiomeric stereoisomers and opposed in the meso stereoisomer. Consistent with piperazinediones of similar size and shape bearing nonpolar or weakly dipolar arene groups, these compounds engage in R22(8) hydrogen bonding, most often forming one-dimensional tapes. However, the preference for arene perpendicular edge-to-center interactions seen in the former is replaced by a preference for parallel edge-to-center arene interactions. While the dipoles of parallel edge-to-center associated arenes are often opposed, this is not a requirement in the solid state.
AB - 1,4-Piperazine-2,5-diones derived from 2-amino-7-nitro-4-methoxyindan-2- carboxylic acid were prepared in meso, racemic, and enantiomerically pure forms, crystallized from DMSO or DMF, and the supramolecular organization in the crystals determined by X-ray crystallography. These molecules were designed to bear two strongly dipolar p-nitroanisole groups, aligned in the enantiomeric stereoisomers and opposed in the meso stereoisomer. Consistent with piperazinediones of similar size and shape bearing nonpolar or weakly dipolar arene groups, these compounds engage in R22(8) hydrogen bonding, most often forming one-dimensional tapes. However, the preference for arene perpendicular edge-to-center interactions seen in the former is replaced by a preference for parallel edge-to-center arene interactions. While the dipoles of parallel edge-to-center associated arenes are often opposed, this is not a requirement in the solid state.
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U2 - 10.1021/cg701240m
DO - 10.1021/cg701240m
M3 - Article
AN - SCOPUS:61549092473
VL - 8
SP - 3257
EP - 3270
JO - Crystal Growth and Design
JF - Crystal Growth and Design
SN - 1528-7483
IS - 9
ER -