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Dihydrogen Bond in the Aminoborane Complex of a Nicergoline Intermediate

1
Department of Solid State Chemistry, University of Chemistry and Technology Prague, Technická 5, 166 28 Prague 6, Czech Republic
2
Teva Czech Industries s.r.o., Research and Development, Ostravská 29, 747 70 Opava-Komárov, Czech Republic
3
Teva Czech Industries s.r.o., Research and Development, Branišovská 31, 370 05 České Budějovice, Czech Republic
*
Author to whom correspondence should be addressed.
Academic Editor: Josef Jampilek
Molecules 2019, 24(14), 2548; https://doi.org/10.3390/molecules24142548
Received: 28 May 2019 / Revised: 25 June 2019 / Accepted: 3 July 2019 / Published: 12 July 2019
(This article belongs to the Special Issue Heterocycles in Medicinal Chemistry)
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Abstract

An aminoborane side product from the nicergoline manufacture process was identified by single-crystal X-ray diffraction. As boranes of pharmaceutical molecules are quite rare, the binding potential of the BH3 group was investigated and compared with similar compounds using Cambridge Structural Database (CSD). Surprisingly, the packing was stabilized by a dihydrogen bond, which triggered a false alert for too-short contact of hydrogen atoms in IUCR checkCIF. As the dihydrogen bond concept is not widely known, such an alert might mislead crystallographers to force –CH3 optimal geometry to –BH3 groups. The B–H distances equal to or less than 1.0 Å (17% of the CSD structures) are substantially biased when analyzing the structures of aminoborane complexes in CSD. To conduct proper searching, B–H bond length normalization should be applied in the CSD search. View Full-Text
Keywords: nicergoline; aminoborane; CSD; single crystal; X-ray structure; dihydrogen bond nicergoline; aminoborane; CSD; single crystal; X-ray structure; dihydrogen bond
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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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Čejka, J.; Cvak, L.; Žižková, S.; Kratochvíl, B.; Jegorov, A. Dihydrogen Bond in the Aminoborane Complex of a Nicergoline Intermediate. Molecules 2019, 24, 2548.

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