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Crystal and Molecular Structure of Three Organic Salts from N6-Benzyladenine, 5-Sulfosalicylic Acid, Naphthalene-1,5-Disulfonic Acid, and α-Ketoglutaric Acid

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Abstract

Three organic salts of the nucleobase of N6-benzyladenine have been prepared with 5-sulfosalicylic acid, naphthalene-1,5-disulfonic acid, and α-ketoglutaric 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 = 10.6684(8) Å, b = 11.3981(9) Å, c = 15.1175(12) Å, α = 71.0290(10)º, β = 77.0130(10)º, γ = 87.404(2)º, V = 1693.2(2) Å3, Z = 2. Compound 2 crystallizes in the triclinic, space group P-1, with a = 7.3941(9) Å, b = 10.4623(11) Å, c = 11.7424(12) Å, α = 102.0570(10), β = 102.6580(10)º, γ = 110.254(2), V = 790.25(15) Å3, Z = 1. Compound 3 crystallizes in the monoclinic, space group P2(1)/c, with a = 5.2150(6) Å, b = 47.960(3) Å, c = 7.3909(8) Å, β = 113.882(2)º, V = 1690.3(3) Å3, Z = 4. In all of the compounds, the N9 atom was protonated. 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···S, N–H···O, and N–H···N interactions as well as other noncovalent C–H···O, CH2···O, C···π, C–H···π, N–H···π, O···π, and π···π interactions, giving higher-dimensional framework structures.

Graphical Abstract

The crystal structures of the N6-benzyladenine salts with 5-sulfosalicylic acid, naphthalene-1,5-disulfonic acid, and α-ketoglutaric acid show extensive classical hydrogen bonding as well as C–H···O, CH2···O, C···π, C–H···π, N–H···π, O···π, and π···π interactions, giving higher-dimensional framework structures.

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Acknowledgments

This research was supported by Zhejiang Provincial Natural Science Foundation of China under Grant No. LY14B010006, the Education Office Foundation of Zhejiang Province under Grant No. Y201017321, the college innovation project of the Shaoxing city (TMKC1472), and the innovation project of the Tianmu College of the Zhejiang A & F University.

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Authors and Affiliations

  1. Jiyang College, Zhejiang A & F University, Zhuji, 311800, People’s Republic of China

    Shouwen Jin, Li Jin, Xianghang Ye, Jingwen Li, Binpeng Jin & Lu Zheng

  2. Zhejiang Provincial Key Laboratory of Chemical Utilization of Forestry Biomass, Zhejiang A & F University, Lin’an, 311300, Zhejiang Province, People’s Republic of China

    Shouwen Jin, Li Jin, Xianghang Ye, Jingwen Li, Binpeng Jin & Lu Zheng

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

    Daqi Wang

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  1. Shouwen Jin
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Correspondence to Shouwen Jin.

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Jin, S., Jin, L., Ye, X. et al. Crystal and Molecular Structure of Three Organic Salts from N6-Benzyladenine, 5-Sulfosalicylic Acid, Naphthalene-1,5-Disulfonic Acid, and α-Ketoglutaric Acid. J Chem Crystallogr 45, 9–19 (2015). https://doi.org/10.1007/s10870-014-0557-8

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