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Crystal and Molecular Structure of Four Organic Salts Assembled from Cyclohexylamine and Organic acids

Research paper by Xingjun Gao, Zhanghui Lin, Shouwen Jin, Guqing Chen, Tiansong Huang, Zuoyi Ji, Ying Zhou, Daqi Wang

Indexed on: 18 Mar '14Published on: 18 Mar '14Published in: Journal of chemical crystallography



Abstract

Four compounds, [(HL)33+ · (cba−)3·2H2O] (1, cba = o-chlorobenzoate), [(HL)+·(NSA−)] (2, NSA− = 5-nitrosalicylate), [(HL)22+·(3,5-dns2−)] (3, 3,5-dns2− = 3,5-dinitrosalicylate), and [(HL)22+·(nda2−)] (4, nda2− = 1,5-naphthalenedisulfonate) were obtained from self-assembly of the corresponding acids with the cyclohexylamine, and their structures were fully characterized. All four compounds are organic salts, with proton transfer occurring to the NH2 of the cyclohexylamine moiety. All structures adopted hetero supramolecular synthons. Compound 1 crystallizes in the triclinic, space group P-1, with a = 10.151(3) Å, b = 13.160(4) Å, c = 17.172(5) Å, α = 72.159(4)°, β = 79.546(4)°, γ = 78.285(4)°, V = 2120.5(11) Å3, Z = 2. Compound 2 crystallizes in the monoclinic, space group P2(1)/c, with a = 13.501(2) Å, b = 6.3144(15) Å, c = 19.601(3) Å, β = 123.900(13)°, V = 1386.9(4) Å3, Z = 4. Compound 3 crystallizes in the monoclinic, space group P2(1)/n, with a = 14.6439(11) Å, b = 6.9231(4) Å, c = 21.3012(18) Å, β = 96.4800(10)°, V = 2145.7(3) Å3, Z = 4. Compound 4 crystallizes in the monoclinic, space group P2(1)/n, with a = 5.3477(5) Å, b = 19.9238(16) Å, c = 11.1761(9) Å, β = 95.7230(10)°, V = 1184.84(17) Å3, Z = 2. Analysis of the crystal packing of 1–4 displays that there are extensive N–H···O hydrogen bonds between the acids and the cyclohexylamine in all of the salts. Except the classical hydrogen bonding interactions, the secondary propagating interactions also play significant roles in structure extension. The four salts displayed 2D/3D framework structures for the synergistic effect of the various noncovalent interactions.

Graphical abstract 10.1007/s10870-014-0503-9.gif