Role of sp-C-H-N hydrogen bonding in crystal engineering
Evidence supporting the central role of alkynyl sp-C-H-N hydrogen bonds in the formation of discrete molecular complexes as well as one-and two-dimensional bimolecular sp-C-H-N hydrogen bonded networks is presented. The crystal structures of seven bimolecular complexes formed between nitrogen-containing aromatics and compounds containing terminal alkynes are reported. The average N-H distance in these structures is 2.35 Å, well below the sum of the van der Waals radii of 2.80 Å, and the average N-H-C bond angle is 173.2°.
Bosch, Eric. "Role of sp-C− H---N Hydrogen Bonding in Crystal Engineering." Crystal growth & design 10, no. 8 (2010): 3808-3813.
Crystal Growth and Design