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

Lawrence J. Williams; B. Jagadish; Michael G. Lansdown; Michael D. Carducci; Eugene A. Mash

doi:10.1016/S0040-4020(99)00924-2

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

Lawrence J. Williams, B. Jagadish, Michael G. Lansdown, Michael D. Carducci, Eugene A. Mash

Chemistry and Biochemistry

Research output: Contribution to journal › Article › peer-review

20 Scopus citations

Abstract

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.

Original language	English (US)
Pages (from-to)	14301-14322
Number of pages	22
Journal	Tetrahedron
Volume	55
Issue number	50
DOIs	https://doi.org/10.1016/S0040-4020(99)00924-2
State	Published - Dec 10 1999

Keywords

Amino acids and derivatives
Indanes
Piperazinones
X-Ray crystal structures

ASJC Scopus subject areas

Biochemistry
Drug Discovery
Organic Chemistry

Access to Document

10.1016/S0040-4020(99)00924-2

Cite this

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. / Williams, Lawrence J.; Jagadish, B.; Lansdown, Michael G. et al.
In: Tetrahedron, Vol. 55, No. 50, 10.12.1999, p. 14301-14322.

Research output: Contribution to journal › Article › peer-review

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title = "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",

abstract = "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.",

keywords = "Amino acids and derivatives, Indanes, Piperazinones, X-Ray crystal structures",

author = "Williams, {Lawrence J.} and B. Jagadish and Lansdown, {Michael G.} and Carducci, {Michael D.} and Mash, {Eugene A.}",

note = "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.",

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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.

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KW - X-Ray crystal structures

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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

Abstract

Keywords

ASJC Scopus subject areas

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CCDC 255269: Experimental Crystal Structure Determination

CCDC 255270: Experimental Crystal Structure Determination

CCDC 255268: Experimental Crystal Structure Determination

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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

Abstract

Keywords

ASJC Scopus subject areas

Access to Document

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Datasets

CCDC 255269: Experimental Crystal Structure Determination

CCDC 255270: Experimental Crystal Structure Determination

CCDC 255268: Experimental Crystal Structure Determination

Cite this