Abstract
4-(E)-2-[3-(3-[(E)-2-(4-cyanophenyl)-1-diazenyl]hexahydro-1-pyrimidinylmethyl)hexahydro-1-pyrimidinyl]-1-diazenylbenzonitrile (1) has been synthesized by reaction of p-cyanobenzene diazonium chloride with a mixture of formaldehyde and 1,3-propanediamine. The crystal structure has been determined by single crystal X-ray diffraction analysis. The bis-triazene (1) adopts a folded conformation, similar to previously studied ethylenediamine analogues, and there is evidence of π-stacking in the crystal packing. The two planar phenyltriazenyl groups are almost parallel, forming an angle of 6.6(1)∘, and display weak intermolecular π ⋅s π interactions between molecules. This result establishes the structure of the product of this diazonium coupling reaction as the 1-(1-hexahydropyimidinylmethyl)hexahydropyrimidine derivative and not the alternate tetraazabicyclo[5.5.1]tridecane derivative. Crystal data: 1C23H26N10, monoclinic, space group P21/c, a = 10.717(1) Å, b = 7.749(1) Å, c = 28.252(2) Å, β = 97.223(2)∘, V = 2327.5(5) Å3, for Z = 4.
Similar content being viewed by others
References
Hooper, D.L.; Peori, M.B.; Vaughan, K. J. Org. Chem. 1998, 63, 7437.
Biradha, K.; Peori, M.B.; Vaughan, K.; Zaworotko, M.J. J. Chem Cryst. 1999, 29, 145.
Otwinowski, Z.; Minor,W. In Methods in Enzymology; Carter, C.W.; Sweet, R.M. Eds.; Academic Press: London; 1997, Vol. 276, Part. A, pp 307–326.
Altomare, A.; Burla, M.C.; Camalli, M.; Cascarano, G.; Giacovazzo, C.; Guagliardi, C.; Moliterni, A.G.; Polidori, C.; Spagna, R. J. Appl. Crystallogr. 1999, 32, 115.
Sheldrick, G.M. SHELXL-97, Program for Refinement of Crystal Structures, University of Göttingen: Germany; 1997.
Nardelli, M. J. Appl. Crystallogr. 1995, 28, 659.
Burnett, M.N.; Johnson, C.K. ORTEP-III, Report ORNL-6895, Oak Ridge National Laboratory: Oak Ridge, TN; 1996.
Cremer, D.; Pople, J.A. J. Am. Chem. Soc. 1975, 97, 1354.
Allen, F.H.; Kennard, O.; Watson, D.G.; Brammer, G.; Orpen, G.; Taylor, R. J. Chem. Soc., Perkin Trans. 2, 1987, S1.
Bertolasi, V.; Glister, J.F.; Vaughan, K. J. Chem. Cryst. 2004, 34, 175.
Fronczek, F.R.; Hansch, C.; Watkins, S.F. Acta. Cryst. 1988, C44, 1651.
Author information
Authors and Affiliations
Corresponding author
Rights and permissions
About this article
Cite this article
Peori, B., Vaughan, K. & Bertolasi, V. 4-(E)-2-[3-(3-[(E)-2-(4-cyanophenyl)-1-diazenyl]hexahydro-1-pyrimidinylmethyl)hexahydro-1-pyrimidinyl]-1diazenylbenzonitrile: X-ray crystal structure. J Chem Crystallogr 35, 297–305 (2005). https://doi.org/10.1007/s10870-005-3248-7
Received:
Accepted:
Issue Date:
DOI: https://doi.org/10.1007/s10870-005-3248-7