Crystals of Benzamide, the First Polymorphous Molecular Compound, Are Helicoidal

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2020
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Shtukenberg, Alexander G.
Drori, Ran
Vidavsky, Netta
Haddad, Asaf
Zheng, Jason
Estroff, Lara A.
Weissman, Haim
Efrati, Efi
Kahr, Bart
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The growth of spontaneously twisted crystals is a common but poorly understood phenomenon. An analysis of the formation of twisted crystals of a metastable benzamide polymorph (form II) crystallizing from highly supersaturated aqueous and ethanol solutions is given here. Benzamide, the first polymorphic molecular crystal reported (1832), would have been the first helicoidal crystal observed had the original authors undertaken an analysis by light microscopy. Polymorphism and twisting frequently concur as they are both associated with high thermodynamic driving forces for crystallization. Optical and electron microscopies as well as electron and powder X‐ray diffraction reveal a complex lamellar structure of benzamide form II needle‐like crystals. The internal stress produced by the overgrowth of lamellae is shown to be able to create a twist moment that is responsible for the observed non‐classical morphologies.

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ISO 690SHTUKENBERG, Alexander G., Ran DRORI, Elena V. STURM, Netta VIDAVSKY, Asaf HADDAD, Jason ZHENG, Lara A. ESTROFF, Haim WEISSMAN, Efi EFRATI, Bart KAHR, 2020. Crystals of Benzamide, the First Polymorphous Molecular Compound, Are Helicoidal. In: Angewandte Chemie International Edition. Wiley. 2020, 59(34), pp. 14593-14601. ISSN 1433-7851. eISSN 1521-3773. Available under: doi: 10.1002/anie.202005738
BibTex
@article{Shtukenberg2020-05-29Cryst-50900,
  year={2020},
  doi={10.1002/anie.202005738},
  title={Crystals of Benzamide, the First Polymorphous Molecular Compound, Are Helicoidal},
  number={34},
  volume={59},
  issn={1433-7851},
  journal={Angewandte Chemie International Edition},
  pages={14593--14601},
  author={Shtukenberg, Alexander G. and Drori, Ran and Sturm, Elena V. and Vidavsky, Netta and Haddad, Asaf and Zheng, Jason and Estroff, Lara A. and Weissman, Haim and Efrati, Efi and Kahr, Bart}
}
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