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An X-ray Crystallographic Study of the Related Triazenes, 1,4-Di[(E)-2-(2-nitrophenyl)-1-diazenyl]piperazine and Methyl 4-{(E)-2-(4-methylpiperazino)-1-diazenyl}benzoate

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Abstract

The crystal structures of methyl 4-{(E)-2-(4-methylpiperazino)-1-diazenyl}benzoate (2a) and 1,4-di[(E)-2-(2-nitrophenyl)-1-diazenyl]piperazine (3a) have been determined by single crystal X-ray diffraction analysis. The bis-triazene (3a) adopts an unusual pseudo-boat conformation in the piperazine ring, with a dihedral angle of 52.20(0.06)° between the two planes defined within the piperazine ring. The crystal structures of 2a and 3a are compared with the structure of the triazene (4) and the closely related bis-triazene (5). The piperazine ring of 2a adopts a typical chair conformation, whereas the piperazine ring of 3a adopts an unusual boat conformation. Crystal data: 2a C13H18N4O2, monoclinic, space group P21 /n, a = 13.849(3) Å, b = 6.577(1) Å, c = 14.904(3) Å, α = 90°, β = 96.098(3)°, γ = 90° and V = 1,349.8(4) Å3, for Z = 4. 3a C16H16N8O4, triclinic, space group P-1, a = 7.6066(6) Å, b = 8.3741(7) Å, c = 14.507(1) Å, α = 78.673(1)°, β = 81.877(1)°, γ = 73.445(1)° and V = 865.0(1) Å3, for Z = 2.

Index abstract

The crystal structures of methyl 4-{(E)-2-(4-methylpiperazino)-1-diazenyl}benzoate (2a) and 1,4-di[(E)-2-(2-nitrophenyl)-1-diazenyl]piperazine (3a) have been determined by single crystal X-ray diffraction analysis.

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Acknowledgements

The authors are grateful to the Natural Sciences and Engineering Research Council of Canada (NSERC) for a Discovery Grant to the principal author (KV) and an Undergraduate Summer Research Award (2003) to Vanessa Little. The authors thank the Faculty of Graduate Studies and Research at Saint Mary’s University for a Summer Research Award (2004) to Vanessa Little.

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Correspondence to Keith Vaughan.

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Little, V.R., Jenkins, H. & Vaughan, K. An X-ray Crystallographic Study of the Related Triazenes, 1,4-Di[(E)-2-(2-nitrophenyl)-1-diazenyl]piperazine and Methyl 4-{(E)-2-(4-methylpiperazino)-1-diazenyl}benzoate. J Chem Crystallogr 38, 447–452 (2008). https://doi.org/10.1007/s10870-008-9340-z

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