Acemetacin cocrystal structures by powder X-ray diffraction

IUCrJ
Geetha BollaAshwini Nangia

Abstract

Cocrystals of acemetacin drug (ACM) with nicotinamide (NAM), p-aminobenzoic acid (PABA), valerolactam (VLM) and 2-pyridone (2HP) were prepared by melt crystallization and their X-ray crystal structures determined by high-resolution powder X-ray diffraction. The powerful technique of structure determination from powder data (SDPD) provided details of molecular packing and hydrogen bonding in pharmaceutical cocrystals of acemetacin. ACM-NAM occurs in anhydrate and hydrate forms, whereas the other structures crystallized in a single crystalline form. The carboxylic acid group of ACM forms theacid-amide dimer three-point synthon R3(2)(9)R2(2)(8)R3(2)(9) with three different syn amides (VLM, 2HP and caprolactam). The conformations of the ACM molecule observed in the crystal structures differ mainly in the mutual orientation of chlorobenzene fragment and the neighboring methyl group, being anti (type I) or syn (type II). ACM hydrate, ACM-NAM, ACM-NAM-hydrate and the piperazine salt of ACM exhibit the type I conformation, whereas ACM polymorphs and other cocrystals adopt the ACM type II conformation. Hydrogen-bond interactions in all the crystal structures were quantified by calculating their molecular electrostatic potential (MEP) su...Continue Reading

References

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Citations

Aug 6, 2019·Acta Crystallographica. Section C, Structural Chemistry·Vasanthi PalanisamyVladimir Chernyshev
Oct 6, 2019·The Journal of Antimicrobial Chemotherapy·Gajapati Y N VarmaArunasree M Kalle
Mar 6, 2018·Acta Crystallographica. Section C, Structural Chemistry·Karolina de Oliveira GonçalvesFelipe T Martins
May 23, 2021·European Journal of Pharmaceutical Sciences : Official Journal of the European Federation for Pharmaceutical Sciences·Ling-Yang WangZhi-Yong Wu

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Methods Mentioned

BETA
X-ray
differential scanning calorimetry
NMR

Software Mentioned

ITO
TREOR
Seed
ConQuest
AUTOX

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