Synthesis, crystal structure, DFT studies, and Hirshfeld surface analysis of N,N'-bis(3-quinolyl-methylene)diphenylethanedione dihydrazone

Abstract

The synthesis, characterization, and theoretical studies of a novel hydrazine, N,N’-bis-(3-quinolylmethylene)diphenylethanedione dihydrazone (1) has been reported. The molecular structure has been characterized by room-temperature single-crystal X-ray diffraction which reveals that two quinoline moieties are disposed nearly perpendicularly around the central C-C bond giving a ‘L’ shape of the molecule. This particular geometry gives rise to the hydrogen-bonded supramolecular rectangle of two self-complementary molecules. These supramolecular units are further assembled by π-π interaction. The Hirshfeld surface analysis of compound 1 shows that C···C, C···H, H···H, and N···H interactions of 13.1, 9.9, 52.3, and 7.4%, respectively, which exposed that the main intermolecular interactions were H···H intermolecular interactions. Crystal data for C₃₄H₂₄N₆: Triclinic, space group P-1 (no. 2), a = 10.885(3) Å, b = 11.134(3) Å, c = 12.870(3) Å, α = 90.122(6)°, β = 114.141(6)°, γ = 110.277(5)°, V = 1316.1(6) Å³, Z = 2, T = 100(2) K, μ(MoKα) = 0.080 mm^-1, Dcalc = 1.304 g/cm³, 7309 reflections measured (3.518° ≤ 2Θ ≤ 39.276°), 2318 unique (R_int = 0.0527, R_sigma = 0.0565) which were used in all calculations. The final R₁ was 0.0416 (I > 2σ(I)) and wR₂ was 0.1074 (all data).