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Synthesis, Characterization and Crystal Structures of 3-Hydroxy-N′-[methyl(2-pyridyl)methylene]-2-naphthohydrazide monohydrate and 3-Hydroxy-N′-(3,5-dibromo-2-hydroxybenzylidene)-2-naphthohydrazide dimethylformamide solvate

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Abstract

Two hydrazone compounds, 3-hydroxy-N′-[methyl(2-pyridyl)methylene]-2-naphthohydrazide monohydrate (1), and 3-hydroxy-N′-(3,5-dibromo-2-hydroxybenzylidene)-2-naphthohydrazide dimethylformamide solvate (2), have been prepared and characterized by elemental analysis, IR spectra, 1HNMR spectra, and X-ray single crystal structural determination. Compound (1) crystallizes in the monoclinic space group C2/c with unit cell dimensions a = 11.072(2) Å, b = 12.017(2) Å, c = 23.753(3) Å, β = 95.710(2)°, V = 3144.7(9) Ǻ3, Z = 8, R 1 = 0.0780, and wR 2 = 0.1465. Compound (2) crystallizes in the triclinic space group P-1 with unit cell dimensions a = 7.601(2) Å, b = 16.522(4) Å, c = 17.048(3) Å, α = 92.516(11)°, β = 96.726(12)°, γ = 94.117(12)°, V = 2117.8(8) Ǻ3, Z = 4, R 1 = 0.0490, and wR 2 = 0.1012. The hydrazone molecules in the compounds adopt trans configurations about the C=N double bonds. The crystal structures of the compounds are stabilized by intermolecular hydrogen bonds and π···π stacking interactions.

Graphical Abstract

Two hydrazone compounds, 3-hydroxy-N′-[methyl(2-pyridyl)methylene]-2-naphthohydrazide monohydrate and 3-hydroxy-N′-(3,5-dibromo-2-hydroxybenzylidene)-2-naphthohydrazide dimethylformamide solvate, are presented.

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Acknowledgments

This research was supported by the National Sciences Foundation of China (No. 20676057 and 20877036) and Top-class foundation of Pingdingshan University (No. 2008010).

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Authors and Affiliations

  1. College of Chemistry and Chemical Engineering, Pingdingshan University, Pingdingshan, 467000, Henan, People’s Republic of China

    Guo-Ping Cheng, Ling-Wei Xue & Wei-Chun Yang

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  1. Guo-Ping Cheng
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  2. Ling-Wei Xue
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  3. Wei-Chun Yang
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Correspondence to Ling-Wei Xue.

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Cheng, GP., Xue, LW. & Yang, WC. Synthesis, Characterization and Crystal Structures of 3-Hydroxy-N′-[methyl(2-pyridyl)methylene]-2-naphthohydrazide monohydrate and 3-Hydroxy-N′-(3,5-dibromo-2-hydroxybenzylidene)-2-naphthohydrazide dimethylformamide solvate. J Chem Crystallogr 42, 668–672 (2012). https://doi.org/10.1007/s10870-012-0297-6

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