Co-crystals
of thiocyanuric acid (TCA) and five multitopic bases
are reported, and their structures are compared. The adducts of all
five co-crystals form two-dimensional hydrogen-bonded sheets that
are either stacked or interpenetrated. Strong N–H···N
hydrogen bonds between TCA and the N-heterocyclic bases are supplemented
by pairs of longer, weaker C–H···S hydrogen
bonds resulting in a motif reminiscent of the complementary triple
hydrogen bond observed between imides and aminopyridines. TCA is observed
to fulfill different roles in the adducts: a 3-fold node with triazine,
a dimer junction exhibiting 4-fold connectivity with pyrazine, 2,7-diazapyrene,
and DABCO, and an extended ribbon with 1,2-di(4-pyridyl)ethylene.
The weak C–H···S hydrogen bonds are seen to
be readily distorted to accommodate favorable packing arrangements
in the adducts with pyrazine and DABCO, suggesting these weak C–H···S
interactions possess a limited role in the direction of topology.
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