Crystal Structures of Three Organic Adducts Produced by N-Benzyladenine, Trichloroacetic Acid, 3-Nitrophthalic Acid, and Citric Acid.

Three organic adducts of N-benzyladenine have been prepared with trichloroacetic acid, 3-nitrophthalic acid, and citric acid. The three crystalline complexes were characterized by X-ray diffraction analysis, IR, mp, and elemental analysis. Compound 1 crystallizes in the triclinic, space group P-1, with a = 5.4634(4) Å, b = 9.7180(7) Å, c = 15.9707(12) Å, α = 84.2100(10)°, β = 86.633(2)°, γ = 78.0640(10)°, V = 824.75(10) Å, Z = 2. Compound 2 crystallizes in the triclinic, space group P-1, with a = 7.4065(7) Å, b = 8.1151(8) Å, c = 18.4782(15) Å, α = 95.3190(10)°, β = 90.7750(10)°, γ = 115.063(2)°, V = 1000.00(16) Å, Z = 2. Compound 3 crystallizes in the triclinic, space group P-1, with a = 5.0883(5) Å, b = 13.0295(11) Å, c = 16.4332(14) Å, α = 69.1550(10)°, β = 83.900(3)°, γ = 79.244(2)°, V = 999.35(15) Å, Z = 2. In 1, the N atom was protonated, thus 1 is a salt. For 2 and 3, all carboxyl groups remain protonated, so 2 and 3 are both cocrystal. These structures adopted homo or hetero supramolecular synthons or both. Analysis of the crystal packing of 1- 3 displays that there are O-H···O, O-H···N, N-H···O, and N-H···N hydrogen bonds as well as C-H···O, CH···O, C-H···Cl, O-O, O-N, Cl···N, Cl···O, Cl···π, CH···π, and π···π interactions, giving 2D/3D framework structures. Graphical Abstract: The crystal structures of the N-benzyladenine adducts with trichloroacetic acid, 3-nitrophthalic acid, and citric acid show extensive classical hydrogen bonding as well as C-H···O, CH···O, C-H···Cl, O-O, O-N, Cl···N, Cl···O, Cl···π, CH···π, and π···π interactions, giving 2D/3D framework structures. [ABSTRACT FROM AUTHOR]