A high-pressure polymorph of propionamide from in situ high-pressure crystallisation from solution

Abstract

The structure of a high-pressure polymorph of propionamide is reported from synchrotron single-crystal X-ray diffraction data. The polymorph was obtained by in situ high-pressure crystallisation from solution in a diamond-anvil cell at 0.9 GPa; its structure is 23% denser than that of the ambient-pressure polymorph at STP. PIXEL lattice and dimer energies calculations indicate that the ambientand high-pressure polymorphs are energetically competitive. Together with acetamide and formamide, this is the third high-pressure polymorph of an aliphatic amide crystallising as a Z′ = 2 structure; the H-bonded network is however significantly different from the ones reported for the other two compounds. This study highlights the power of in situ high-pressure crystallisation techniques for accessing novel polymorphic forms of molecular compounds.

Intermolecular interaction energies in transition metal coordination compounds

“…10 The results can be used to visualise contributing energy terms using Hirshfeld surfaces 11 or energy vectors or frameworks. [12][13][14] This progress has been applied to areas such as polymorphism 15 and energy landscapes, 16 cocrystals and solvates, 17 crystal engineering, 18 molecular recognition 19 and extreme conditions research. 20 The techniques listed above have been applied extensively in work on organic materials.…”

On modelling disordered crystal structures through restraints from molecule-in-cluster computations, and distinguishing static and dynamic disorder

“…7) and the two archetype structures optimize to distinct nonplanar local minima. At room temperature, modelling two split sites does not improve the modelling (Fabbiani et al, 2014) and an overall weaker fit to the data of the conformational average with single positions was observed. This can be explained by moving away from an ideal crystal with more perfect translational symmetry at room temperature.…”

“…Computations performed in our earlier study (Dittrich et al, 2020a) on the drug subset were partly relied upon for these structures. Their diffraction data were deposited alongside publications in the journals of Acta Crystallographica sections C and E. For two further examples, propionamide (Fabbiani et al, 2014) and DL-arginine monohydrate (Kingsford-Adaboh et al, 2002) data were collected by the author. Intensity data are usually embedded in deposited CIFs today.…”

“…This permitted adding three further examples, which were randomly selected based on disorder being reported from a search in the CSD. The datasets used were: I, methyl (4-bromophenyl)(3-tert-butyl-1H-indol-1-research papers yl)acetate, refcode CAWWIJ (Arredondo et al, 2017); II, erlotinib, refcode DULKAX (Sridhar et al, 2010); III, 4-(4methoxyphenyl)piperazin-1-ium (MeOPP) 4-fluorobenzoate monohydrate, refcode FOVPOY (Kiran Kumar et al, 2019); IV, DL-arginine monohydrate, refcode FUGXIO01 with intensity data (lattice parameters) from a subsequent chargedensity study (Kingsford-Adaboh et al, 2000; V, 1-(2bromo-3-{[tert-butyl(dimethyl)silyl]oxy}phenyl)-2,2-dimethylbut-3-en-1-yl 4-nitro-benzoate, refcode IRUMAL (Ghosh & Kassekert, 2016); VI, telaprevir, refcode LERJID (Gelbrich et al, 2013); VII, irbesartan bromide sesquihydrate, refcode NIQVIT (Wang et al, 2007); VIII, duloxetine hydrochloride, refcode MUCDUK (Bhadbhade et al, 2009); IX, darifenacin hydrobromide, refcode SOYMID (Selvanayagam et al, 2009); and X, propionamide, refcode ZZZKAY03 at 100 K (Fabbiani et al, 2014). For propionamide there is an additional roomtemperature structure relevant here, with refcode ZZZKAY05 (Fabbiani et al, 2014).…”

Cocrystals of Gallic Acid with Urea and Propionamide: Supramolecular Structures, Hirshfeld Surface Analysis, and DFT Studies

“…Urea and propionamide, two Food and Drug Administration (FDA) status aliphatic acyclic amides, have been identified as coformers. Urea with two hydrogen bond donor (─NH 2 ) groups and a hydrogen bond acceptor (C═O) group, propionamide with a hydrogen bond donor (─NH 2 ) group and a hydrogen bond acceptor (C═O) group can demonstrate a remarkable ability to form hydrogen bonds which are necessary for the formation of cocrystals. Expected supramolecular arrangements are shown in Scheme .…”