Abstract
Piperazine-2,5-diones derived from 2-amino-7-cyano-4-methoxyindan-2-carboxylic acid were prepared in meso, racemic, and enantiomerically pure forms, crystallized from dimethyl sulfoxide (DMSO), and the supramolecular organization in the crystals determined by X-ray crystallography. These molecules were designed to bear two strongly polar p-methoxybenzonitrile moieties either aligned or opposed. In contrast with nonpolar or weakly polar piperazinediones of similar size and shape, which exclude DMSO to form ladder-like tapes by reciprocal intermolecular amide-to-amide hydrogen bonding, these more strongly polar piperazinediones participate in hydrogen bonding with included DMSO. In cocrystals of the enantiomerically pure compounds, the p-methoxybenzonitrile dipoles were aligned in the three-dimensional lattice but opposed by the dipoles of included DMSO. These cocrystals exhibited second harmonic properties comparable to urea. A second cocrystal possessing aligned p-methoxybenzonitrile dipoles was observed when the enantiomerically pure compound was crystallized from dipropylsulfoxide. Compensating dipropylsulfoxide dipoles were absent in this cocrystal.
Original language | English (US) |
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Pages (from-to) | 811-821 |
Number of pages | 11 |
Journal | Crystal Growth and Design |
Volume | 3 |
Issue number | 5 |
DOIs | |
State | Published - Sep 2003 |
ASJC Scopus subject areas
- Chemistry(all)
- Materials Science(all)
- Condensed Matter Physics
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Dive into the research topics of 'Organic crystal engineering with piperazine-2,5-diones. 4. Crystal packing of piperazinediones derived from 2-amino-7-cyano-4-methoxyindan-2-carboxylic acid'. Together they form a unique fingerprint.Datasets
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CCDC 221266: Experimental Crystal Structure Determination
Jagadish, B. (Creator), Carducci, M. D. (Creator), Bosshard, C. (Creator), Günter, P. (Contributor), Margolis, J. I. (Creator), Williams, L. J. (Creator) & Mash, E. A. (Creator), Cambridge Crystallographic Data Centre, 2004
DOI: 10.5517/cc7f7mh, http://www.ccdc.cam.ac.uk/services/structure_request?id=doi:10.5517/cc7f7mh&sid=DataCite
Dataset
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CCDC 221267: Experimental Crystal Structure Determination
Jagadish, B. (Creator), Carducci, M. D. (Creator), Bosshard, C. (Creator), Günter, P. (Contributor), Margolis, J. I. (Creator), Williams, L. J. (Creator) & Mash, E. A. (Creator), Cambridge Crystallographic Data Centre, 2004
DOI: 10.5517/cc7f7nj, http://www.ccdc.cam.ac.uk/services/structure_request?id=doi:10.5517/cc7f7nj&sid=DataCite
Dataset
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CCDC 221265: Experimental Crystal Structure Determination
Jagadish, B. (Creator), Carducci, M. D. (Creator), Bosshard, C. (Creator), Günter, P. (Contributor), Margolis, J. I. (Creator), Williams, L. J. (Creator) & Mash, E. A. (Creator), Cambridge Crystallographic Data Centre, 2004
DOI: 10.5517/cc7f7lg, http://www.ccdc.cam.ac.uk/services/structure_request?id=doi:10.5517/cc7f7lg&sid=DataCite
Dataset