Authors: Howie, R. A.; De Souza, M.V.N.; Lima, C.H.S.; Wardell, J.L.; Wardell, S.M.S.V.
AbstractThe molecule of (E)-3-(3-MeOC6H4CH=CHCO)-benzotriazole 1-oxide, 2, has a very near planar structure, while the 2-nitrophenyl ring is rotated out of the plane of the remaining atoms in (E)-3-(2-O2NC6H4CH=CHCO)-benzotriazole 1-oxide, 1. The nitrogen oxide bond lengths in 1 and 2 are 1.258 (6) and 1.2683 (15) Å, respectively, and are in the region found for related compounds. There are no strong intermolecular hydrogen-bonds in either compound, instead there are weak C–H···O intermolecular hydrogen-bonds and π···π stacking interactions in 1, and C–H···O, C–H···π, and π···π stacking interactions in 2. Different three-dimensional arrays are generated in each case. Compound 1 crystallises in the orthorhombic space group Pna21, with a = 25.061 (2) Å, b = 3.6997 (2) Å, c = 14.2623 (12) Å and Z = 4. Compound 2 crystallises in the triclinic space group P-1, with a = 5.7297 (3) Å, b = 10.8440 (6) Å, c = 11.4965 (6) Å, α = 89.689 (3)°, β = 76.019 (3)°, γ = 75.047 (3)°, Z = 2.
Keywords: Benzotriazole 1-oxides Hydrogen-bonds π···π Stacking interactions Supramolecular arrangementsDocument Type: Research ArticleDOI: http://dx.doi.org/10.1007/s10870-011-0260-yPublication date: 7 de Fevereiro de 2012