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Open AccessArticle

Co-Crystal with Unusual High Z′ and Z′′ Values Derived from Hexamethylenetetramine and 4-fluorophenol (1/1)

1
Universidad Nacional de Colombia, Sede Bogotá, Facultad de Ciencias, Departamento de Química, Síntesis de Heterociclos, Carrera 30 No. 45-03, Bogotá 111321, Colombia
2
Institut für Anorganische Chemie, J. W. Goethe-Universität Frankfurt, Max-von Laue-Str., 7, 60438 Frankfurt/Main, Germany
*
Author to whom correspondence should be addressed.
Crystals 2019, 9(10), 520; https://doi.org/10.3390/cryst9100520
Received: 24 August 2019 / Revised: 7 October 2019 / Accepted: 9 October 2019 / Published: 10 October 2019
(This article belongs to the Section Crystal Engineering)
The title co-crystal, 1,3,5,7-tetraazatricyclo[3.3.1.13,7]decane (HMTA, 1)–4-fluorophenol (4-FP) (1/1), C6H12N4·C6H5FO, shows an unusual asymmetric unit that comprises eight independent molecules (Z′′ = 8), four for each component, with four formula units per asymmetric unit (Z′ = 4). In the molecular packing, each HMTA molecule bridges one 4-FP molecule via an O−H···N hydrogen bond to form a two-molecule aggregate. Differences can be observed between the bond lengths and angles of the independent HMTA and 4-FP molecules and those of the molecules in the aggregate. The C−N bonds exhibit different bond lengths in the tetrahedral cage-like structure of the HMTA molecules, but the largest differences between the molecular aggregates are in the bond lengths in the 4-fluorophenol ring. In the crystal, the HMTA and 4-FP molecules form two hydrogen-bonded (O−H···N, C−H···F and C−H···O) dimers of HMTA and 4-FP molecules, A···D and B···C inversion dimers, which generate enlarged R88(34) ring motifs in both supramolecular structures. In both structures, the crystal packing also features additional C−H···F and C−H···O interactions. The A···D and B···C dimers are linked by additional C−H···F and C−H···O hydrogen bonds, forming columns along the a and b axes, respectively. The importance of the C−H···F interaction to the structure and crystal packing has been demonstrated. View Full-Text
Keywords: crystal structure; urotropine; hydrogen bonding; halogen bonding; C−H···F; mechanochemistry crystal structure; urotropine; hydrogen bonding; halogen bonding; C−H···F; mechanochemistry
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Rivera, A.; Sadat-Bernal, J.; Ríos-Motta, J.; Bolte, M. Co-Crystal with Unusual High Z′ and Z′′ Values Derived from Hexamethylenetetramine and 4-fluorophenol (1/1). Crystals 2019, 9, 520.

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