Mixed halobenzenes also prefer face⋯face approaches of aromatic rings, revealing a new inversion symthon

Black, Simon

doi:10.1039/d3ce00276d

CrystEngComm

2023

DOI: 10.1039/d3ce00276d

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Mixed halobenzenes also prefer face⋯face approaches of aromatic rings, revealing a new inversion symthon

Simon Black

Abstract: Analysis of known crystal structures of halobenzenes reveals that the 176 closest intermolecular interactions contain either edge…face or face…face approaches between aromatic rings. Most of these close approaches possess the...

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2024

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Cited by 2 publications

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The interplay between hydrogen bonds and stacking/T-type interactions in molecular cocrystals

Cruz-Cabeza,

Spackman,

Hall

2024

Commun Chem

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Supramolecular synthon and hydrogen bond pairing approaches have influenced the understanding of cocrystal formation for decades, but are hydrogen bonds really the dominant interaction in cocrystals? To investigate this, an extensive analysis of 1:1 two-component cocrystals in the Cambridge Structural Database was undertaken, revealing that stacking and T-type interactions are just as, if not more important than hydrogen bonds in molecular cocrystals. A total of 84% of the most common coformers in the dataset are aromatic. When analysing cocrystal dimers, only 20% consist of solely strong hydrogen bonds, with over 50% of contacts involving stacking and T-type interactions. Combining interaction strength and frequency, both hydrogen bond and stacking/T-type interactions contribute equally to the stabilisation of cocrystal lattices. Therefore, we state that crystal engineering and cocrystal design concepts of the future should not solely revolve around supramolecular synthon pairing via hydrogen bonds, but instead consider optimising both hydrogen bonding and stacking/T-type interactions.

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The interplay between hydrogen bonds and stacking/T-type interactions in molecular cocrystals

Cruz-Cabeza,

Spackman,

Hall

2024

Commun Chem

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Symthons reveal how fluorine disrupts π–π stacking in halobenzene crystal structures

Black,

Davey

2024

CrystEngComm

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Mixed halobenzenes also prefer face⋯face approaches of aromatic rings, revealing a new inversion symthon

Abstract: Analysis of known crystal structures of halobenzenes reveals that the 176 closest intermolecular interactions contain either edge…face or face…face approaches between aromatic rings. Most of these close approaches possess the...

Cited by 2 publications

References 22 publications

The interplay between hydrogen bonds and stacking/T-type interactions in molecular cocrystals

The interplay between hydrogen bonds and stacking/T-type interactions in molecular cocrystals

Symthons reveal how fluorine disrupts π–π stacking in halobenzene crystal structures

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