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Crystals 2019, 9(2), 71; https://doi.org/10.3390/cryst9020071

New Crystal Forms for Biologically Active Compounds. Part 1: Noncovalent Interactions in Adducts of Nevirapine with XB Donors

Saint Petersburg State University, Saint Petersburg 199034, Russia
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Received: 12 January 2019 / Revised: 25 January 2019 / Accepted: 29 January 2019 / Published: 30 January 2019
(This article belongs to the Special Issue Halogen-Bonded Cocrystals)
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Abstract

Stabilization of specific crystal polymorphs of an active pharmaceutical ingredient is crucial for preventing uncontrollable interconversion of various crystalline forms, which affects physicochemical properties as well as physiological activity. Co-crystallization with various excipients is an emerging productive way of achieving such stabilization in the solid state. In this work, we identified an opportunity for co-crystallization of antiviral drug nevirapine (NVP) with a classical XB donor, 1,2,4,5-tetrafluoro-3,6-diiodobenzene (1,4-FIB), as well as 1,3-diiodobenzene (1,3-DIB), which has been seldom employed as an XB donor to date. In the X-ray structures of NVP·1,4-FIB and NVP·1,3-DIB co-crystals, different hydrogen and halogen bonding modes were detected and further investigated via DFT calculations as well as topological analysis of the electron density distribution within the framework of the QTAIM method at the M06/DZP-DKH level of theory. Estimated energies of these supramolecular contacts vary from 0.6 to 5.7 kcal/mol. View Full-Text
Keywords: nevirapine; crystal engineering; noncovalent interactions; halogen bonding; hydrogen bonding; DFT; QTAIM nevirapine; crystal engineering; noncovalent interactions; halogen bonding; hydrogen bonding; DFT; QTAIM
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This is an open access article distributed under the Creative Commons Attribution License which permits unrestricted use, distribution, and reproduction in any medium, provided the original work is properly cited (CC BY 4.0).

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Kryukova, M.A.; Sapegin, A.V.; Novikov, A.S.; Krasavin, M.; Ivanov, D.M. New Crystal Forms for Biologically Active Compounds. Part 1: Noncovalent Interactions in Adducts of Nevirapine with XB Donors. Crystals 2019, 9, 71.

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