2-Cyano-2-isonitrosoacetamide–3,4-dimethylpyrazole (1/1): a co-crystal of two molecules with agrochemical activities

In the structure of the title co-crystal, C3H3N3O2·C5H8N2, the components are linked by a set of directional O—H⋯N, N—H⋯O, N—H⋯N and C—H⋯O hydrogen bonds to yield a two-dimensional mono-periodic arrangement. The structure propagates in the third dimension by extensive π–π stacking inter­actions of nearly parallel mol­ecules of the two components, following an alternating sequence. The primary structure-defining inter­action is very strong oxime-OH donor to pyrazole-N acceptor hydrogen bond [O⋯N = 2.587 (2) Å], while the significance of weaker hydrogen bonds and π–π stacking inter­actions is comparable. The distinct structural roles of different kinds of inter­actions agree with the results of a Hirshfeld surface analysis and calculated inter­action energies. The title compound provides insights into co-crystals of active agrochemical mol­ecules and features the rational integration in one structure of a fungicide, C3H3N3O2, and a second active component, C5H8N2, known for alleviation the toxic effects of fungicides on plants. The material appears to be well suited for practical uses, being non-volatile, air-stable, water-soluble, but neither hygroscopic nor efflorescent.

Domasevitch, K. V., Senchyk, G. A., Ponomarova, V. V., Lysenko, A. B., & Krautscheid, H. (2024). 2-Cyano-2-isonitrosoacetamide–3,4-dimethylpyrazole (1/1): a co-crystal of two molecules with agrochemical activities. Acta Crystallographica Section E Crystallographic Communications, 80(5), pp. 439-445. doi:10.1107/s2056989024002809