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Issue 7, 2011
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Uncommon crystal motif of brucine in its diastereomeric salt with (11-oxo-11H-dibenzo[b,f][1,4]thiazepin-10-yl)-acetic acid: a case of possible crystallization-induced dynamic resolution

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Abstract

The paper reports on the molecular and crystal structure of the diastereomeric salt (4) formed by the (11-oxo-11H-dibenzo[b,f][1,4]thiazepin-10-yl)-acetate (H−12) and the brucinium resolving agent. Experimental evidences suggest that the salt was obtained by a crystallization-induced dynamic resolution of the tricyclic compound 2, which seems to constitute the first example of successful application of this technique to tricycles of this kind. A systematic comparison with already published structural data of compounds containing brucine (molecule/ion) evidences that in 4 the resolving cation assembles in an unusual host framework. A review of the solid state structures containing brucine/brucinium moieties available in the literature provides some simple rules which help to exclude/identify a priori the supramolecular host (brucine molecule/ion) framework.

Graphical abstract: Uncommon crystal motif of brucine in its diastereomeric salt with (11-oxo-11H-dibenzo[b,f][1,4]thiazepin-10-yl)-acetic acid: a case of possible crystallization-induced dynamic resolution

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Publication details

The article was received on 01 Sep 2010, accepted on 15 Dec 2010 and first published on 25 Jan 2011


Article type: Paper
DOI: 10.1039/C0CE00595A
Citation: CrystEngComm, 2011,13, 2310-2317
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    Uncommon crystal motif of brucine in its diastereomeric salt with (11-oxo-11H-dibenzo[b,f][1,4]thiazepin-10-yl)-acetic acid: a case of possible crystallization-induced dynamic resolution

    M. Altamura, A. Guidi, L. Jierry, P. Paoli and P. Rossi, CrystEngComm, 2011, 13, 2310
    DOI: 10.1039/C0CE00595A

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