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

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Abstract

Four compounds, [(HL) 3+3 · (cba−)3·2H2O] (1, cba = o-chlorobenzoate), [(HL)+·(NSA−)] (2, NSA− = 5-nitrosalicylate), [(HL) 2+2 ·(3,5-dns2−)] (3, 3,5-dns2− = 3,5-dinitrosalicylate), and [(HL) 2+2 ·(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

The crystal structures of the cyclohexylamine salts with o-chlorobenzoic acid, 5-nitrosalicylic acid, 3,5-dinitrosalicylic acid, and 1,5-naphthalenedisulfonic acid show extensive classical hydrogen bonding as well as C–H···O, CH2···O, Cl···O, NH3···π, CH2···π, and π···π interactions, giving 2D sheets or 3D networks.

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Acknowledgments

We gratefully acknowledge the financial support of the Education Office Foundation of Zhejiang Province (Project No. Y201017321) and the financial support of the Zhejiang A & F University Science Foundation (Project No. 2009FK63).

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Authors and Affiliations

  1. TianMu College, ZheJiang A & F University, Lin’An, 311300, People’s Republic of China

    Xingjun Gao, Zhanghui Lin, Shouwen Jin, Guqing Chen, Tiansong Huang, Zuoyi Ji & Ying Zhou

  2. Department of Chemistry, Liaocheng University, Liaocheng, 252059, People’s Republic of China

    Daqi Wang

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  1. Xingjun Gao
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  2. Zhanghui Lin
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Correspondence to Shouwen Jin.

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Gao, X., Lin, Z., Jin, S. et al. Crystal and Molecular Structure of Four Organic Salts Assembled from Cyclohexylamine and Organic acids. J Chem Crystallogr 44, 210–219 (2014). https://doi.org/10.1007/s10870-014-0503-9

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  • DOI: https://doi.org/10.1007/s10870-014-0503-9

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