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Synthesis and Crystal Structure of a New Diphenylglycoluril Derivative

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Abstract

The title compound has been synthesized by alkylation of diphenylglycoluril with o-xylylenedihalides followed by Sonogashira cross-coupling reaction. The yielded product 2 was investigated with X-ray crystallographic, NMR, EI-MS, and IR techniques. The crystal belongs to a triclinic system, space group P-1 with unit cell parameters a = 10.5057(8) Å, b = 12.6915(9) Å, c = 13.3426(10) Å, α = 83.8540(10)o, β = 87.9360(10)o, γ = 75.5700(10)o, V = 1712.9(2) Å3, Z = 2, D c  = 1.322, M r  = 681.59, μ = 0.232 mm−1, F(000) = 708, R 1  = 0.0586 and wR 2  = 0.1470.

Graphical Abstract

Two molecules of 2 undergo dimerazation due to the formation of two self-complementary N–H···O = C interactions to yield the R 2 2 (8) hydrogen bonding motif.

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Acknowledgments

The authors would like to express their thanks to Xianggao Meng for performing the x-ray crystallographic measurements and gratefully acknowledge the financial support of this work by the National Natural Science Foundation of China (Grant Number 20902035).

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Authors and Affiliations

  1. Key Laboratory of Pesticide and Chemical Biology, Ministry of Education, College of Chemistry, Central China Normal University, Wuhan, 430079, People’s Republic of China

    Yan Chen, Nengfang She & Anxin Wu

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  1. Yan Chen
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  2. Nengfang She
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  3. Anxin Wu
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Correspondence to Nengfang She.

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Chen, Y., She, N. & Wu, A. Synthesis and Crystal Structure of a New Diphenylglycoluril Derivative. J Chem Crystallogr 41, 791–795 (2011). https://doi.org/10.1007/s10870-010-9977-2

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  • DOI: https://doi.org/10.1007/s10870-010-9977-2

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