The Crystal Structure of Orthocetamol Solved by 3D Electron Diffraction

Andrusenko, Iryna; Hamilton, Victoria; Mugnaioli, Enrico; Lanza, Arianna; Hall, Charlie L.; Potticary, Jason; Hall, Simon R.; Gemmi, Mauro

doi:10.1002/anie.201904564

Cited by 46 publications

(62 citation statements)

References 41 publications

(17 reference statements)

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“…The hydrogen positions (in black) are stable once incorporated to the dynamical refinement. (B) Two adjacent orthocetamol chains 34 with the superimposed difference Fourier map. The maximum residual potential (in blue and yellow) corresponds to the hydrogen atom responsible for the intermolecular bonding.…”

Section: Dynamical Refinementmentioning

confidence: 99%

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3D Electron Diffraction: The Nanocrystallography Revolution

et al. 2019

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Crystallography of nanocrystalline materials has witnessed a true revolution in the past 10 years, thanks to the introduction of protocols for 3D acquisition and analysis of electron diffraction data. This method provides single-crystal data of structure solution and refinement quality, allowing the atomic structure determination of those materials that remained hitherto unknown because of their limited crystallinity. Several experimental protocols exist, which share the common idea of sampling a sequence of diffraction patterns while the crystal is tilted around a noncrystallographic axis, namely, the goniometer axis of the transmission electron microscope sample stage. This Outlook reviews most important 3D electron diffraction applications for different kinds of samples and problematics, related with both materials and life sciences. Structure refinement including dynamical scattering is also briefly discussed.

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Section: Dynamical Refinementmentioning

confidence: 99%

“…31,32 Additionally, ED allows for a better structural resolution and requires an electron dose much lower than any imaging technique, as testified by the successful structure determinations of very beam sensitive materials, 21,26,30,35,46−50,56,68,73 possibly even without the need of cooling down the sample. 24,29,34,55,62…”

Section: Introductionmentioning

confidence: 99%

3D Electron Diffraction: The Nanocrystallography Revolution

et al. 2019

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“…Its commercially used form I exhibits poor compactability, unless specially prepared as porous microballs (Ogienko et al, 2011), and so this compound remains of great interest with respect to the search for new solid forms applicable for direct compression (Haisa et al, 1976;Espeau et al, 2005;Keshavarz et al, 2019). In addition, since paracetamol is known for its hepatotoxicity (Bunchorntavakul & Reddy, 2013;Njoku, 2014), structurally similar compounds are of interest (McGregor et al, 2015;Andrusenko et al, 2019). In particular, one of the possible alternatives is metacetamol [or N-(3-hydroxyphenyl)acetamide], the closest analogue and isomer of paracetamol (Hadi et al, 2013).…”

Section: Introductionmentioning

confidence: 99%

A novel crystal form of metacetamol: the first example of a hydrated form

et al. 2019

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We report the crystal structure and crystallization conditions of a first hydrated form of metacetamol (a hemihydrate), C 8 H 9 NO 2 Á0.5H 2 O. It crystallizes from metacetamol-saturated 1:1 (v/v) water-ethanol solutions in a monoclinic structure (space group P2 1 /n) and contains eight metacetamol and four water molecules per unit cell. The conformations of the molecules are the same as in polymorph II of metacetamol, which ensures the formation of hydrogen-bonded dimers and R 2 2 (16) ring motifs in its crystal structure similar to those in polymorph II. Unlike in form II, however, these dimers in the hemihydrate are connected through water molecules into infinite hydrogen-bonded molecular chains. Different chains are linked to each other by metacetamol-water and metacetamol-metacetamol hydrogen bonds, the latter type being also present in polymorph I. The overall noncovalent network of the hemihydrate is well developed and several types of hydrogen bonds are responsible for its formation. research papers Acta Cryst. (2019). C75, 1465-1470 Zemtsova et al. A novel crystal form of metacetamol

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“…The intensity of the electron beam should be reduced to the minimum, the microscope should be equipped with a direct electron detector, and the data collection should be carried out in the continuous mode. 24 Using these precautions, the total dose can be reduced to 1 el Å À2 , and nanocrystals of very beam sensitive materials such as API 34,35 or even proteins 36 can be fully characterized through 3D ED.…”

Section: Discussionmentioning

confidence: 99%

A New Method Based on Electron Diffraction for Detecting Nanoparticles in Injectable Medicines

Gemmi

Serravalle²,

Sarsina³

2020

Journal of Pharmaceutical Sciences

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A new method for detecting and characterizing nanoparticles in an injectable pharmaceutical solution is presented. The method is based on the simultaneous use, on those nanoparticles that are crystalline, of three-dimensional electron diffraction tomography and energy dispersive X-ray spectrometry. With three-dimensional electron diffraction tomography, the unit cell and the crystal symmetry of the nanoparticles are determined, while with energy dispersive X-ray spectrometry, the chemical composition is derived. With these data, through an inspection of a crystallographic database, it is possible to determine the crystal phase of the nanoparticles. The knowledge of the crystal phase is a valuable element for understanding the provenance and the formation of the nanoparticles, helping the researcher in solving any quality control issue related to the presence of nanoparticles in an injectable solution.

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The Crystal Structure of Orthocetamol Solved by 3D Electron Diffraction

Abstract: Supportinginformation and the ORCID identification number(s) for the author(s) of this article can be found under: https://doi.

Cited by 46 publications

References 41 publications

3D Electron Diffraction: The Nanocrystallography Revolution

3D Electron Diffraction: The Nanocrystallography Revolution

A novel crystal form of metacetamol: the first example of a hydrated form

A New Method Based on Electron Diffraction for Detecting Nanoparticles in Injectable Medicines

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