Crystal and Molecular Structures of Five 3D Organic Salts from 2,6-Dimethylaniline and Organic Acids

Abstract

Five crystalline organic acid-base salts [(HL)·(dnsa−), L = 2,6-dimethylaniline, dnsa− = 3,5-dinitrosalicylate] (1), [(HL+)·(4-Hnpta−), 4-Hnpta− = 4-nitrophthalate] (2), [(HL)2·(nds)·(H2O)2, nds = 1,5-naphthalenedisulfonate] (3), [(HL)·(dnb)·(Hdnb), dnb = 3,5-dinitrobenzoate, Hdnb = 3,5-dinitrobenzoic acid] (4) and [(HL)·(dca), dca = dichloroacetate] (5) from 2,6-dimethylaniline and organic acids were prepared and characterized by XRD analysis, IR, mp and elemental analysis. Compound 1 adopts the triclinic, space group Pī, with a = 7.6261(6) A, b = 8.3429(8) A, c = 13.1147(12) A, α = 91.3610(10)o, β = 102.755(2)o, γ = 102.597(2)o, V = 791.96(12) A3, Z = 2. Compound 2 belongs to the monoclinic, space group P2(1)/c, with a = 14.2552(15) A, b = 8.1436(8) A, c = 14.5708(13) A, α = 90°, β = 113.795(2)o, γ = 90°, V = 1547.7(3) A3, Z = 4. Compound 3 crystallizes in the monoclinic, space group P2(1)/c, with a = 8.4784(7) A, b = 17.4798(15) A, c = 9.1119(8) A, α = 90°, β = 99.742(2)o, γ = 90°, V = 1330.9(2) A3, Z = 2. Compound 4 has orthorhombic, space group Pna2(1), with a = 24.5029(19) A, b = 7.5322(9) A, c = 26.665(2) A, α = 90°, β = 90°, γ = 90°, V = 4921.3(8) A3, Z = 8. Compound 5 crystallizes in the monoclinic, space group C2/c, with a = 19.8970(17) A, b = 11.1850(11) A, c = 13.1590(12) A, α = 90°, β = 123.408(3)o, γ = 90°, V = 2444.6(4) A3, Z = 8. For 1 it was the relatively weak phenol that has ionized, different from 2 to 5. All supramolecular architectures of 1–5 involve N–H⋯O H-bonds as well as CH3⋯O interactions. The other noncovalent interactions (CH⋯O, CH⋯Cl, O⋯C, O⋯N, O⋯O, Cl⋯Cl, C⋯π, O⋯π, CH3⋯π and π⋯π) in the crystal packing were also ascertained. These weak interactions combined, all compounds displayed 3D framework structures. In the five prepared supramolecular assemblies there are plenty of weak bonding interactions such as directional H-bonds of N–H⋯O, O–H⋯O, O–H⋯S, O–H⋯N and noncovalent bonds of CH⋯O, CH3⋯O, CH⋯Cl, O⋯C, O⋯N, O⋯O, Cl–Cl, C⋯π, O⋯π, CH3⋯π, and aryl⋯aryl interactions. All compounds displayed the 3D framework structures