TY - JOUR
T1 - Organic crystal engineering with piperazine-2,5-diones. 2. Crystal packing of weakly dipolar piperazinediones derived from 2-amino-4-bromo-7- methoxyindan-2-carboxylic acid
AU - Williams, Lawrence J.
AU - Jagadish, B.
AU - Lansdown, Michael G.
AU - Carducci, Michael D.
AU - Mash, Eugene A.
N1 - Funding Information:
Financial support of this research from Research Corporation, from the Office of Naval Research through the Center for Advanced Multifunctional Nonlinear Optical Polymers and Molecular Assemblies, and from the University of Arizona through the Materials Characterization Program and the Office of the Vice President for Research is gratefully acknowledged. Assistance from Dr. Michael Bruck and the staff of the Molecular Structure Lab at the University of Arizona Department of Chemistry, and from Dr. Victor G. Young, Jr., of the X-ray Crystallographic Laboratory at The University of Minnesota, is gratefully acknowledged.
PY - 1999/12/10
Y1 - 1999/12/10
N2 - Piperazine-2,5-diones with the potential to manifest three chemically distinct and linearly independent intermolecular interactions were synthesized from the enantiomers of 2-amino-4-bromo-7-methoxyindan-2- carboxylic acid. Samples of enantiomerically pure, racemic, and meso piperazinediones were characterized in the solid state by X-ray crystallography. 'Ladder-like' intermolecular amide-to-amide hydrogen bonding interactions were observed in each case, establishing tape structures parallel to one crystallographic axis. The observed tape morphologies and crystal packing closely resemble that previously observed for a topographically similar tetramethoxy-piperazinedione. The results obtained demonstrate that the weak dipoles associated with the p-bromoanisole moiety play no role in determining order in the crystalline state.
AB - Piperazine-2,5-diones with the potential to manifest three chemically distinct and linearly independent intermolecular interactions were synthesized from the enantiomers of 2-amino-4-bromo-7-methoxyindan-2- carboxylic acid. Samples of enantiomerically pure, racemic, and meso piperazinediones were characterized in the solid state by X-ray crystallography. 'Ladder-like' intermolecular amide-to-amide hydrogen bonding interactions were observed in each case, establishing tape structures parallel to one crystallographic axis. The observed tape morphologies and crystal packing closely resemble that previously observed for a topographically similar tetramethoxy-piperazinedione. The results obtained demonstrate that the weak dipoles associated with the p-bromoanisole moiety play no role in determining order in the crystalline state.
KW - Amino acids and derivatives
KW - Indanes
KW - Piperazinones
KW - X-Ray crystal structures
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U2 - 10.1016/S0040-4020(99)00924-2
DO - 10.1016/S0040-4020(99)00924-2
M3 - Article
AN - SCOPUS:0033544756
VL - 55
SP - 14301
EP - 14322
JO - Tetrahedron
JF - Tetrahedron
SN - 0040-4020
IS - 50
ER -