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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References
Little VR, Vaughan K (2004) Can J Chem 82:1294
Moser SL, Vaughan K (2004) Can J Chem 82:1725
Little VR, Tingley R, Vaughan K (2005) Can J Chem 83:471
Moser SL, Church R, Peori MB, Vaughan K (2005) Can J Chem 83:1071
Tingley R, Peori MB, Church R, Vaughan K (2005) Can J Chem 83:1799
Glister JF, Vaughan K (2006) J Het Chem 43:217
Yanarates E, Disli A, Yildirir Y (1999) Org Prep Proc Int Briefs 31:429
Kažemėkaitė M, Talaikytė Z, Niaura G, Butkus E (2002) Molecules 7:706
Lalezari I, Afgahi F (1975) J Pharm Sci 64:698
Mazza M, Pagani G, Calderara G, Vicarini L (1973) Farmaco Ed Sci 28:846
Sheldrick GM (1996) SADABS: Sheldrick GM (ed) Germany, Univ. Göttingen
Sheldrick GM (1994) SHELXTL, Release 5.03: Siemens Analytical X-ray Instruments Inc.; Madison, Wisconsin
Burnett MN, Johnson CK (1996) ORTEP-III [computer program]. Oak Ridge National Laboratory, Oak Ridge, Tenn
Allen FH, Kennard O, Watson DG, Branmer G, Orpen G, Taylor R (1987) J Chem Soc Perkin Trans 2:S1
Carpy A, Saxena AK (1991) Acta Cryst C47:227
Ravikumar K, Sridar B (2005) Acta Cryst E61:o3245
Thirumurugan R, Vengadesan K, Shanmuga Sundara Raj S, Shanmugam G, Fun H-K (2000) Cryst Res Technol 35:987
Paital AR, Nanda PK, Das S, Aromi G, Raj D (2006) Inorg Chem 45:505
Bullerwell WL, MacGillivray LR, Zaworotko MJ, Vaughan K, Wilman DEV (1995) Acta Crystallogr C51:2624
Vaughan K, Turner E, Jenkins H (2004) Can J Chem 82:448
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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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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DOI: https://doi.org/10.1007/s10870-008-9340-z