Abstract
The single-crystal structure of the title compound, C4H10N2·2C6F3I3, features a moderately strong halogen bond between one of the three crystallographically distinct iodine atoms and the nitro-gen atom. The iodine-nitro-gen distance is 2.820 (3) Å, corresponding to 80% of the sum of their van der Waals radii. The C-I⋯N halogen bond angle is 178.0 (1)°, consistent with the linear inter-action of nitro-gen via a σ-hole opposite the carbon-iodine covalent bond. The other two iodine atoms do not engage in halogen bonding. Some weak C-H⋯F and -H⋯I interactions are also observed. The complete piperazine molecule is generated by symmetry.
Highlights
The single-crystal structure of the title compound, C4H10N2Á2C6F3I3, features a moderately strong halogen bond between one of the three crystallographically distinct iodine atoms and the nitrogen atom
The iodine–nitrogen distance is 2.820 (3) A, corresponding to 80% of the sum of their van der Waals radii
The other two iodine atoms do not engage in halogen bonding
Summary
The halogen bond is a moderately strong and directional non-covalent interaction, which has proven very useful in the field of crystal engineering and for the design of cocrystalline materials. Perfluorinated iodobenzenes are commonly used as halogen-bond donors, in part due to their reliable ability to co-crystallize predictably with a range of electron donors (Cavallo, 2016). The iodine–nitrogen distance is 2.820 (3) A , which corresponds to 80% of the sum of their van der Waals radii. This is somewhat shorter than the analogous iodine–nitrogen halogen bonds in co-crystals formed from the same halogen-bond donor with acridine (3.022 A ), 1,10-phenanthroline (3.020 and 3.148 A ), or 2,3,5,6-tetramethylpyrazine (2.991 and 2.993 A ), but comparable to those formed with hexamethylenetetramine (2.864 and 2.879 A ) as the electron donor (Szell et al, 2017).
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