Electrical, magnetic, and structural characterisation of 4-cyano-1,3,6-triazacycl[3.3.3]azine

Abstract

4-Cyano-1,3,6-triazacycl[3.3.3]azine crystallises in the monoclinic system, space group P2₁/c. with a= 6.411(4). b= 15.366(6), c= 9.211(5)Å, β= 104.30(5)°, U= 879.3 ų, Z= 4, D_c= 1.48 Mg m^–3. The structure was solved by direct methods and refined to a final R of 0.045 for 737 observed reflections. The molecules are arranged in distorted columns, parallel to c, with two types of overlap and interplanar spacings of 3.09 and 3.31 Å which alternate, The crystals show semiconductive behaviour with ρ= 2 × 10⁹Ω cm at 300 K, the properties arising from charge transfer interactions between the acceptor atoms of the cyano group and the donor atoms of the ring. The closest intermolecular non-hydrogen contacts are C(3a)–C(10′)= 3.153(6), C(4)–C(10′)= 3.293(6), and N(9b)–N(11′)= 3.159(5)Å. In contrast, 1,3,4,6-tetra-azacycl[3.3.3]azine and its 2,5-dimethyl analogue have ρ_{300 K} > 10¹⁴Ω cm and all intermolecular contacts are of the van der Waals type.