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Crystal Structure of Dacarbazine, Metoclopramide, and Acetylcholine Pentacyanopropenides

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Abstract

The crystal structures of new salt forms of the known nitrogen-containing pharmaceuticals (dacarbazine, metoclopramide, and acetylcholine) in which 1,1,2,3,3-pentacyanopropenide anion acts as a counterion are analyzed by X-ray diffraction. It is found that in the crystals of studied salts with dacarbazine (in the form of a monohydrate) and metoclopramide, the mentioned anion plays the role of a structure-forming spacer, linking with more than one cation by classical hydrogen bonds. The types of cation and anion localization in the studied salts are revealed. They are: layered in the crystals with dacarbazine, stacked with the cation and anion alternation in the crystals with metoclopramide, and anion columns surrounded by cations in the crystals with acetylcholine. The tendency of the pentacyanopropenide anion to disordering in the crystals of metoclopramide and acetylcholine salts is detected.

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Funding

The study was supported by the Russian Science Foundation grant (project No. 19-73-00107). Diffraction experiments were performed using the facilities of the Spectral Analytical Center, Kazan Scientific Center, Russian Academy of Sciences.

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Authors and Affiliations

  1. Arbuzov Institute of Organic and Physical Chemistry, Kazan Scientific Center, Kazan, Russia

    S. A. Shteingolts, R. R. Fayzullin & O. A. Lodochnikova

  2. Ulianov Chuvash State University, Cheboksary, Russia

    V. V. Davydova, M. A. Mar’yasov & O. E. Nasakin

Authors
  1. S. A. Shteingolts
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  2. V. V. Davydova
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  3. M. A. Mar’yasov
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  4. O. E. Nasakin
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  5. R. R. Fayzullin
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  6. O. A. Lodochnikova
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Corresponding authors

Correspondence to R. R. Fayzullin or O. A. Lodochnikova.

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Russian Text © The Author(s), 2020, published in Zhurnal Strukturnoi Khimii, 2020, Vol. 61, No. 6, pp. 980–990.

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Shteingolts, S.A., Davydova, V.V., Mar’yasov, M.A. et al. Crystal Structure of Dacarbazine, Metoclopramide, and Acetylcholine Pentacyanopropenides. J Struct Chem 61, 928–937 (2020). https://doi.org/10.1134/S002247662006013X

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  • DOI: https://doi.org/10.1134/S002247662006013X

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