Four related benzazepine derivatives in a reaction pathway leading to a benzazepine carboxylic acid: hydrogen-bonded assembly in zero, one, two and three dimensions

Guerrero, Sergio A.; Sanabria, Carlos M.; Palma, Alirio; Cobo, Justo; Glidewell, Christopher

doi:10.1107/s2053229614006007

Cited by 5 publications

(2 citation statements)

References 22 publications

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“…Retrieving conglomerate crystals from this database is further frustrated by the difficulties in their prediction. While efforts to rationalize conglomerate crystallization have been conducted using crystal structure prediction, structural modifications, − and supramolecular interactions, , currently only direct measurements of the physical characteristics of a crystal can identify conglomerate behavior conclusively.…”

Section: Introductionmentioning

confidence: 99%

Identifying a Hidden Conglomerate Chiral Pool in the CSD

Walsh

Barclay

Begg

et al. 2022

JACS Au

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Conglomerate crystallization is the spontaneous generation of individually enantioenriched crystals from a nonenantioenriched material. This behavior is responsible for spontaneous resolution and the discovery of molecular chirality by Pasteur. The phenomenon of conglomerate crystallization of chiral organic molecules has been left largely undocumented, with no actively curated list available in the literature. While other crystallographic behaviors can be interrogated by automated searching, conglomerate crystallizations are not identified within the Cambridge Structural Database (CSD) and are therefore not accessible by conventional automated searching. By conducting a manual search of the CSD and literature, a list of over 1800 chiral species capable of conglomerate crystallization was curated by inspection of the racemic synthetic routes described in each publication. The majority of chiral conglomerate crystals are produced and published by synthetic chemists who seldom note and rarely exploit the implications this phenomenon can have on the enantiopurity of their crystalline materials. With their structures revealed, we propose that this list of compounds represents a new chiral pool which is not tied to biological sources of chirality.

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Section: Introductionmentioning

confidence: 99%

Identifying a Hidden Conglomerate Chiral Pool in the CSD

Walsh

Barclay

Begg

et al. 2022

JACS Au

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“…Nor can a conglomerate crystallisation be predicted. Whilst efforts to rationalise conglomerate crystallisation have been conducted using crystal structure predication [44] structural modifications, [45][46][47] and supramolecular interactions, [48,49] currently only direct measurements of the physical characteristics of a crystal can identify conglomerate behaviour conclusively.…”

Section: Introductionmentioning

confidence: 99%

A Potentially Limitless Chiral Pool via Conglomerate Crystallisation: Unidentified Spontaneous Resolution in the CSD.

Walsh

Barclay

Begg

et al. 2022

Preprint

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Conglomerate crystallisation is the behaviour responsible for spontaneous resolution and the discovery of molecular chirality by Pasteur. The phenomenon of conglomerate crystallisation of chiral organic molecules has been left largely undocumented and offers synthetic chemists a potential new chiral pool not reliant on biological systems to supply stereochemical information. While other crystallographic behaviours can be interrogated by automated searching, conglomerate crystallisations are not identified within the Cambridge Structural Database (CSD) and are therefore not accessible by conventional means. By conducting a manual search of the CSD, a list of over 1,700 chiral species capable of conglomerate crystallisation was curated by inspection of the synthetic routes described in each publication. The majority of these are produced by synthetic chemists who seldom note and rarely exploit the implications this phenomenon can have on the enantioenrichment of their crystalline materials. We propose that this list represents a limitless chiral pool which will continually grow in size as more conglomerate crystals are synthesised and recorded.

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