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Molecular Structures Polymorphism the Role of F…F Interactions in Crystal Packing of Fluorinated Tosylates

1
A.N.Nesmeyanov Institute of Organoelement Compounds of Russian Academy of Sciences, 119991 Moscow, Russia
2
Federal Scientific Research Center “Crystallography and Photonics” of Russian Academy of Sciences, 119333 Moscow, Russia
*
Author to whom correspondence should be addressed.
Crystals 2019, 9(5), 242; https://doi.org/10.3390/cryst9050242
Received: 19 April 2019 / Revised: 4 May 2019 / Accepted: 5 May 2019 / Published: 7 May 2019
(This article belongs to the Special Issue Chemical Bonding in Crystals and Their Properties)
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Abstract

The peculiarities of interatomic interactions formed by fluorine atoms were studied in four tosylate derivatives p-CH3C6H4OSO2CH2CF2CF3 and p-CH3C6H4OSO2CH2(CF2)nCHF2 (n = 1, 5, 7) using X-ray diffraction and quantum chemical calculations. Compounds p-CH3C6H4OSO2CH2(CF2)nCHF2 (n = 1, 5) were crystallized in several polymorph modifications. Analysis of intermolecular bonding was carried out using QTAIM approach and energy partitioning. All compounds are characterized by crystal packing of similar type and the contribution of intermolecular interactions formed by fluorine atoms to lattice energy is raised along with the increase of their amount. The energy of intra- and intermolecular F…F interactions is varied in range 0.5–13.0 kJ/mol. Total contribution of F…F interactions to lattice energy does not exceed 40%. Crystal structures of studied compounds are stabilized mainly by C-H…O and C-H…F weak hydrogen bonds. The analysis of intermolecular interactions and lattice energies in polymorphs of p-CH3C6H4OSO2CH2(CF2)nCHF2 (n = 1, 5) has shown that most stabilized are characterized by the least contribution of F…F interactions. View Full-Text
Keywords: organofluorine compounds; polymorphism; QTAIM; NCI; quantum chemical calculations; lattice energy; intermolecular interactions; F…F interactions organofluorine compounds; polymorphism; QTAIM; NCI; quantum chemical calculations; lattice energy; intermolecular interactions; F…F interactions
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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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Arkhipov, D.E.; Lyubeshkin, A.V.; Volodin, A.D.; Korlyukov, A.A. Molecular Structures Polymorphism the Role of F…F Interactions in Crystal Packing of Fluorinated Tosylates. Crystals 2019, 9, 242.

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