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Unclassical Hydrogen Bonds of C–H⋯N and C–H⋯Cl in the Crystal Structures of 2-((E)-1,3-diarylallylidene)malononitriles

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Abstract

The 2-((E)-3-(2-nitrophenyl)-1-(4-methoxyphenyl)allylidene)malononitrile and 2-((E)-3-(2-chlorophenyl)-1-(4-bromophenyl)allylidene)malononitrile were synthesized and characterized by IR, 1H NMR, and elemental analysis. The molecular structures were further confirmed by X-ray diffraction analysis. The former 1, C19H13N3O3, is triclinic, space group P−1, a = 7.3834(13), b = 10.901(3), c = 11.227(2) Å, α = 88.64(2), β = 71.596(14), γ = 78.186(18), Z = 2, V = 838.5(3) Å3. The unclassical hydrogen bond of C–H⋯N links the molecules forming polymers. The latter 2, C36H20Br2Cl2N4, is orthorhombic, space group Pnma, a = 20.900 (4), b = 7.0710 (11), c = 10.9170 (18) Å, Z = 2, V = 1613.4(5) Å3. The same hydrogen bond of C–H⋯N and another type of C–H⋯Cl hydrogen bond link the adjacent molecules forming polymers along a axis.

Index Abstract

The 2-((E)-3-(2-nitrophenyl)-1-(4-methoxyphenyl)allylidene)malononitrile and 2-((E)-3-(2-chlorophenyl)-1-(4-bromophenyl)allylidene)malononitrile were synthesized and characterized by IR, 1H NMR and elemental analysis. The molecular structures were further confirmed by X-ray diffraction analysis. The former 1, C19H13N3O3, is triclinic, space group P−1, a = 7.3834(13), b = 10.901(3), c = 11.227(2) Å, α = 88.64(2), β = 71.596(14), γ = 78.186(18), Z = 2, V = 838.5(3) Å3. The unclassical hydrogen bond of C–H⋯N links the molecules forming polymers. The latter 2, C36H20Br2Cl2N4, is orthorhombic, space group Pnma, a = 20.900 (4), b = 7.0710 (11), c = 10.9170 (18) Å, Z = 2, V = 1613.4(5) Å3. The same hydrogen bond of C–H⋯N and another type of C–H⋯Cl hydrogen bond link the adjacent molecules forming polymers along a axis.

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Acknowledgments

We are grateful to the National Natural Science foundation of China (20802061), the Natural Science foundation (08KJD150019) and Qing Lan Project (08QLT001) of Jiangsu Education Committee for financial support.

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Authors and Affiliations

  1. School of Chemistry and Chemical Engineering, Xuzhou Normal University, Xuzhou, 221116, Jiangsu, People’s Republic of China

    Xiang-Shan Wang, Qing Li & Jian-Rong Wu

  2. The Key Laboratory of Biotechnology on Medical Plant of Jiangsu Province, Xuzhou, 221116, China

    Xiang-Shan Wang & Mei-Mei Zhang

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  1. Xiang-Shan Wang
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  2. Qing Li
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  3. Jian-Rong Wu
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  4. Mei-Mei Zhang
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Correspondence to Xiang-Shan Wang.

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Wang, XS., Li, Q., Wu, JR. et al. Unclassical Hydrogen Bonds of C–H⋯N and C–H⋯Cl in the Crystal Structures of 2-((E)-1,3-diarylallylidene)malononitriles. J Chem Crystallogr 41, 59–63 (2011). https://doi.org/10.1007/s10870-010-9837-0

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