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Cocrystallization of N-donor type compounds with 5-sulfosalicylic acid: The effect of hydrogen-bonding supramolecular architectures

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Abstract

Benzotriazole, N,N′-dimethylpiperazine and N-methylpiperazine were applied to crystallize with 5-sulfosalicylic acid (5-H2SSA), affording three new binary molecular cocrystals [(C6H6N3 +)·(C7H5O6S−)]·H2O (1), [(C6H16N2 2+)1/2·(C7H5O6S−)]·H2O (2) and [(C5H14N2 2+)·(C7H5O6S−)2]·3H2O (3) under general conditions. Proton-transferring occurs from acid to nitrogen of N-donor compounds in all compounds 1, 2 and 3. Analysis of the hydrogen-bonding synthons and their effects on crystal packing were also presented in the context of crystal engineering and host-guest chemistry. In compound 1, 1-D infinite chains are extended to a 2-D layered architecture via strong O-H…O hydrogen bonds and then to a 3-D network by N-H…O interactions. Compou 2 and 3 both have the 1-D chain which is formed by O-H…O bonds and weak C-H…O hydrogen bonds. A common intramolecular S(6) [synthon I] ring is formed by the hydroxyl with the carboxyl group in all three compounds.

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Authors and Affiliations

  1. State Key Laboratory of Crystal Materials, Shandong University, Jinan, 250100, China

    Lei Wang, XiFeng Lu & XuTang Tao

  2. Key Laboratory of Eco-chemical Engineering, Ministry of Education; College of Chemistry and Molecular Engineering, Qingdao University of Science and Technology, Qingdao, 266042, China

    Lei Wang, LingYan Xu, RuiFeng Xue & RuiXin Chen

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  1. Lei Wang
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  2. LingYan Xu
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  3. RuiFeng Xue
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  4. XiFeng Lu
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  5. RuiXin Chen
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  6. XuTang Tao
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Correspondence to XuTang Tao.

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Wang, L., Xu, L., Xue, R. et al. Cocrystallization of N-donor type compounds with 5-sulfosalicylic acid: The effect of hydrogen-bonding supramolecular architectures. Sci. China Chem. 55, 138–144 (2012). https://doi.org/10.1007/s11426-011-4394-8

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  • DOI: https://doi.org/10.1007/s11426-011-4394-8

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