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Durka K, Luliński S, Jarzembska KN, et al. Competition between hydrogen and halogen bonding in the structures of 5,10-dihydroxy-5,10-dihydroboranthrenes. Acta Crystallogr B Struct Sci Cryst Eng Mater. 2014;70:157-71doi: 10.1107/S2052520613034987.
Durka, K., Luliński, S., Jarzembska, K. N., Smętek, J., Serwatowski, J., & Woźniak, K. (2014). Competition between hydrogen and halogen bonding in the structures of 5,10-dihydroxy-5,10-dihydroboranthrenes. Acta crystallographica Section B, Structural science, crystal engineering and materials, 70157-71. https://doi.org/10.1107/S2052520613034987
Durka, Krzysztof, et al. "Competition between hydrogen and halogen bonding in the structures of 5,10-dihydroxy-5,10-dihydroboranthrenes." Acta crystallographica Section B, Structural science, crystal engineering and materials vol. 70 (2014): 157-71. doi: https://doi.org/10.1107/S2052520613034987
Durka K, Luliński S, Jarzembska KN, Smętek J, Serwatowski J, Woźniak K. Competition between hydrogen and halogen bonding in the structures of 5,10-dihydroxy-5,10-dihydroboranthrenes. Acta Crystallogr B Struct Sci Cryst Eng Mater. 2014 Feb;70:157-71. doi: 10.1107/S2052520613034987. Epub 2014 Jan 16. PMID: 24441139.
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Acta Crystallogr B Struct Sci Cryst Eng Mater. 2014 Feb;70:157-71. doi: 10.1107/S2052520613034987. Epub 2014 Jan 16.

Competition between hydrogen and halogen bonding in the structures of 5,10-dihydroxy-5,10-dihydroboranthrenes.

Acta crystallographica Section B, Structural science, crystal engineering and materials

Krzysztof Durka, Sergiusz Luliński, Katarzyna N Jarzembska, Jaromir Smętek, Janusz Serwatowski, Krzysztof Woźniak

Affiliations

  1. Department of Chemistry, Warsaw University of Technology, Noakowskiego 3, Warszawa 00-664, Poland.
  2. Department of Chemistry, University of Warsaw, Pasteura 1, Warszawa 02-093, Poland.

PMID: 24441139 DOI: 10.1107/S2052520613034987

Abstract

X-ray crystallographic and computational studies are reported for a series of boranthrenes, substituted with halogen atoms. The role of competitive hydrogen (O-H...O, O-H...F, C-H...O) and halogen (Cl...Cl, O...Br, F...F) bonding interactions on the molecular arrangement in the crystal structures is discussed. The structural analysis and calculations reveal that the O-H...O hydrogen bond in the unsubstituted derivative 5,10-dihydroxy-5,10-dihydroboranthrene, C12H10B2O2, is of moderate strength (ca -20 kJ mol(-1)), but weaker than that in the related thiophene derivative 4,8-dihydro-4,8-dihydroxy-p-diborino[2,3-b:5,6-b]dithiophene, C8H6B2O2S2 (ca -40 kJ mol(-1)). This is due to shielding of the OH group by the H atoms in the β-position of the boranthrene unit. Structural diversity derived from the flexibility of the O-H...O hydrogen bond facilitates the occurrence of other competitive interactions. For instance, in the 1,6-difluoro derivative, C12H8B2F2O2, the crystal packing results from O-H...F and F...F interactions. In turn, the 1,6-dibromo derivative, C12H8B2Br2O2, is dominated by Br...O halogen-bond interactions. In the most interesting case, the 1,6-dichloro derivative, C12H8B2Cl2O2, molecular disorder leads to the formation of two different supramolecular arrangements co-existing in the crystal lattice, one based on the Cl...Cl and C-H...O bonds, and the other stabilized by O-H...O hydrogen bonds. Calculations performed with density-functional theory (DFT; CRYSTAL09) and PIXEL methodologies show that both lattices are characterized by similar energy values (ca -100 kJ mol(-1)). A mixed arrangement with random or short-range-ordered molecular orientations can also be expected.

Keywords: X-ray structural analysis; boranthrenes; energy calculations; halogen bonding; hydrogen bonding

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