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Crystal and Molecular Structures of N-(5-Chloro-2-hydroxy-phenyl)-acetamide and Its Co-crystal with 3,5-Dinitrobenzoic Acid

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Abstract

Two crystalline compounds N-(5-chloro-2-hydroxy-phenyl)-acetamide [L] (1), and (N-(5-chloro-2-hydroxy-phenyl)-acetamide): (3,5-dinitrobenzoic acid) [(L) · (3,5-Hdns), 3,5-Hdns = 3,5-dinitrobenzoic acid] (2) were prepared and characterized by X-ray diffraction analysis, IR, mp, and elemental analysis. Compound 1 crystallizes in the monoclinic, space group C2/c, with a = 9.9833(7) Å, b = 10.7789(8) Å, c = 16.1622(14) Å, β = 92.8010(10)°, V = 1737.1(2) Å3, Z = 8. Compound 2 crystallizes in the monoclinic, space group C2/c, with a = 32.818(3) Å, b = 6.9900(5) Å, c = 14.8431(12) Å, β = 90.5340(10)°, V = 3404.8(5) Å3, Z = 8. Both supramolecular architectures of the compounds 1–2 involve N–H···O/O–H···O/C–H···O hydrogen bonds as well as other non-covalent association. The role of these non-covalent interactions in the crystal packing is ascertained. These weak interactions combined, the compounds displayed 1D–3D structures.

Graphical Abstract

The crystal structures of the N-(5-chloro-2-hydroxy-phenyl)-acetamide and its co-crystal with 3,5-dinitrobenzoic acid show the classical hydrogen bonding as well as CH–O, CH3–O, and π···π interactions, giving higher dimensional networks.

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Acknowledgements

We gratefully acknowledge the financial support of the Zhejiang Provincial Natural Science Foundation (LY14B010006) and the financial support of the Education Office Foundation of Zhejiang Province (Project No. Y201017321).

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Authors and Affiliations

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

    Xinchen Chi, Lanqing Wang, Shouwen Jin, Ying Zhao & Zhaohui Tao

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

    Daqi Wang

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  1. Xinchen Chi
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  2. Lanqing Wang
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  3. Shouwen Jin
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  4. Daqi Wang
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Correspondence to Shouwen Jin.

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Chi, X., Wang, L., Jin, S. et al. Crystal and Molecular Structures of N-(5-Chloro-2-hydroxy-phenyl)-acetamide and Its Co-crystal with 3,5-Dinitrobenzoic Acid. J Chem Crystallogr 49, 155–161 (2019). https://doi.org/10.1007/s10870-018-0753-z

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