Received 14 August 2013
The title compound, C26H22N5O4P3·C3H6O, has been achieved in a two-step synthesis that does not require chromatography. This molecule contains a seven-membered spirocyclic ring at two P-atom positions and a five-membered ring containing new P-N bonds at the other P-atom position. Endocyclic torsion angles about the central biphenyl C-C bonds are -41.5 (3) and -44.4 (3)°, and P-N bonds of the central P3N3 ring are within the range 1.5665 (17)-1.6171 (17) Å, while the P-O distances are in the range 1.5940 (14)-1.6041 (14) Å. One N-H group makes an intermolecular N-HN hydrogen bond, forming centrosymmetric dimers, while the other N-H group makes an N-HO hydrogen bond to the acetone solvent molecule. The crystal was a two-component non-merohedral twin with ratio 0.811/0.189.
For phosphazene-based flame retardants, see: Bakos et al. (1982); Drews & Barker (1985). For related structures, bond angles and lengths, see: Allcock (1972); Ciftci et al. (2013). For the geometry of phosphazene rings, see: Olthof (1969); Barclay et al. (2002). For the synthesis, see: Allen (1991); Carriedo et al. (1996). For related structures, see: Chandrasekhar et al. (2007; 2011; 2012); Harmjanz et al. (2004). For graph-set analysis, see: Etter (1990). For ring asymmetry parameters, see: Duax et al. (1976).
Data collection: APEX2 (Bruker, 2011); cell refinement: SAINT (Bruker, 2011); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 for Windows (Farrugia, 2012); software used to prepare material for publication: SHELXL97.
Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: JJ2173 ).
We would like to thank Dr Casey Grimm for the MS analysis. Upgrade of the diffractometer was made possible by grant No. LEQSF(2011-12)-ENH-TR-01, administered by the Louisiana Board of Regents.
Allcock, H. R. (1972). In Phosphorus-Nitrogen Compounds. New York: Academic Press, Inc.
Allen, C. W. (1991). Chem. Rev. 91, 119-135.
Bakos, D., Kosik, M., Antos, K., Karolyova, M. & Vyskocil, I. (1982). Fire Mater. 6, 10-11.
Barclay, T. M., Hicks, R. G., Ichimura, A. S. & Patenaude, G. W. (2002). Can. J. Chem. 80, 1501-1506.
Bruker (2011). APEX2 and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.
Carriedo, G. A., Fernandez-Catuxo, L., Alonso, F. J. G., Gomez-Elipe, P. & Gonzalez, P. A. (1996). Macromolecules, 29, 5320-5325.
Chandrasekhar, V., Pandey, M. D., Das, B., Mahanti, B., Gopal, K. & Azhakar, R. (2011). Tetrahedron, 67, 6917-6926.
Chandrasekhar, V., Senapati, T., Dey, A., Das, S., Kalisz, M. & Clérac, R. (2012). Inorg. Chem. 51, 2031-2038.
Chandrasekhar, V., Thilagar, P., Krishnan, V., Bickley, J. F. & Steiner, A. (2007). Cryst. Growth Des. 7, 668-675.
Ciftci, G. Y., Ecik, E. T., Yildirim, T., Bilgin, K., Senkuytu, E., Yuksel, F., Uludag, Y. & Kilic, A. (2013). Tetrahedron, 69, 1454-1461.
Drews, M. J. & Barker, R. H. (1985). Cellulose Chemistry and its applications, edited by T. P Nevell & S. H. Zeronian, pp. 423-454. John Wiley & Sons, Inc.
Duax, W. L., Weeks, C. M. & Rohrer, D. C. (1976). Topics in Stereochemistry, Vol. 9, edited by E. L. Eliel & N. Allinger, New York: New York: John Wiley, pp. 271-383.
Etter, M. C. (1990). Acc. Chem. Res. 23, 120-126.
Farrugia, L. J. (2012). J. Appl. Cryst. 45, 849-854.
Harmjanz, M., Piglosiewicz, I. M., Scott, B. L. & Burns, C. J. (2004). Inorg. Chem. 43, 642-650.
Olthof, R. (1969). Acta Cryst. B25, 2040-2045.
Sheldrick, G. (2004). TWINABS. University of Göttingen, Germany.
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.