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Crystal and Molecular Structures of Quinolin-8-ol and its Salts with Acetylenedicarboxylic Acid, and Butane-1,2,3,4-tetracarboxylic Acid

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Abstract

The crystalline compounds quinolin-8-ol (1) and its two salts 2, and 3 have been prepared and structurally characterized. Compound 1 crystallizes in the triclinic, space group P-1, with a = 6.5775(5) Å, b = 7.8285(6) Å, c = 14.4617(13) Å, α = 96.099(2), β = 92.4700(10)°, γ = 106.171(3), V = 709.09(10) Å3, Z = 4. Compound 1 is a new polymorph of quinolin-8-ol, and displays as dimer. Compound 2 crystallizes in the monoclinic, space group P2(1)/n, with a = 7.4815(11) Å, b = 18.844(3) Å, c = 8.0396(8) Å, β = 94.069(10), V = 1130.5(3) Å3, Z = 4. Compound 3 crystallizes in the triclinic, space group P-1, with a = 7.0968(6) Å, b = 8.6854(7) Å, c = 11.0494(11) Å, α = 105.169(2), β = 90.3700(10)°, γ = 106.031(2), V = 629.50(10) Å3, Z = 1. In the compound 3, the middle two COOH groups were ionized. In the compounds 2 and 3, as predicted on the basis of pKa differences, proton transfer from the COOH group to the hetero-nitrogen of the quinolin-8-ol molecule occurs, resulting in the formation of the hydrogen or dihydrogen salts. In neither of the compounds (2 and 3) the primary cyclic hydrogen-bonded R 22 (8) A–B heterodimer was formed, involving the second oxygen of the anion and the 8-hydroxy substituent of quinolin-8-ol. Instead, this molecule acts in a bridging mode to link the associated molecular units into chain polymers via combination of hydrogen bonds and other nonbonding interactions. The role of these non-covalent interactions in the crystal packing is analyzed. Under these weak interactions, compounds 2 and 3 displayed 3D framework structures.

Graphical Abstract

The crystal structures of quinolin-8-ol and its two salts from acetylenedicarboxylic acid, and butane-1,2,3,4-tetracarboxylic acid display extensive classical hydrogen bonding as well as other non-covalent CH–O, CH2–O, O–Cπ, CH–Cπ, and π···π interactions, giving 0/3D 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 National Training Programs of Innovation and Entrepreneurship of China for Undergraduates under Grant No. 201410341022, and the Zhejiang A & F University Science Foundation under Grant No. 2009FK63.

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Authors and Affiliations

  1. Jiyang College, ZheJiang A & F University, Zhu’ji, 311800, People’s Republic of China

    Kai Xu, Shouwen Jin & Li Jin

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

    Kai Xu, Shouwen Jin & Li Jin

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

    Daqi Wang

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  1. Kai Xu
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  2. Shouwen Jin
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Correspondence to Shouwen Jin.

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Xu, K., Jin, S., Wang, D. et al. Crystal and Molecular Structures of Quinolin-8-ol and its Salts with Acetylenedicarboxylic Acid, and Butane-1,2,3,4-tetracarboxylic Acid. J Chem Crystallogr 45, 290–299 (2015). https://doi.org/10.1007/s10870-015-0590-2

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  • DOI: https://doi.org/10.1007/s10870-015-0590-2

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