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Volume 69 
Part 9 
Pages o1491-o1492  
September 2013  

Received 14 August 2013
Accepted 23 August 2013
Online 31 August 2013

Key indicators
Single-crystal X-ray study
T = 100 K
Mean [sigma](C-C) = 0.003 Å
R = 0.037
wR = 0.102
Data-to-parameter ratio = 13.1
Details
Open access

1,1',4,5-Tetrahydrotrispiro[1,3,2-diazaphosphole-2,2'-[1,3,5,2,4,6]triazatriphosphinine-4',6''-dibenzo[d,f][1,3,2]dioxaphosphepine-6',6'''-dibenzo[d,f][1,3,2]dioxaphosphepine] acetone monosolvate

aUnited States Department of Agriculture Cotton Chemistry and Utilization, 1100 Robert E. Lee Blvd, New Orleans, LA 70124, USA, and bDepartment of Chemistry, Louisiana State University, Baton Rouge, LA 70803, USA
Correspondence e-mail: michael.easson@ars.usda.gov

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-H...N hydrogen bond, forming centrosymmetric dimers, while the other N-H group makes an N-H...O hydrogen bond to the acetone solvent molecule. The crystal was a two-component non-merohedral twin with ratio 0.811/0.189.

Related literature

For phosphazene-based flame retardants, see: Bakos et al. (1982[Bakos, D., Kosik, M., Antos, K., Karolyova, M. & Vyskocil, I. (1982). Fire Mater. 6, 10-11.]); Drews & Barker (1985[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.]). For related structures, bond angles and lengths, see: Allcock (1972[Allcock, H. R. (1972). In Phosphorus-Nitrogen Compounds. New York: Academic Press, Inc.]); Ciftci et al. (2013[Ciftci, G. Y., Ecik, E. T., Yildirim, T., Bilgin, K., Senkuytu, E., Yuksel, F., Uludag, Y. & Kilic, A. (2013). Tetrahedron, 69, 1454-1461.]). For the geometry of phosphazene rings, see: Olthof (1969[Olthof, R. (1969). Acta Cryst. B25, 2040-2045.]); Barclay et al. (2002[Barclay, T. M., Hicks, R. G., Ichimura, A. S. & Patenaude, G. W. (2002). Can. J. Chem. 80, 1501-1506.]). For the synthesis, see: Allen (1991[Allen, C. W. (1991). Chem. Rev. 91, 119-135.]); Carriedo et al. (1996[Carriedo, G. A., Fernandez-Catuxo, L., Alonso, F. J. G., Gomez-Elipe, P. & Gonzalez, P. A. (1996). Macromolecules, 29, 5320-5325.]). For related structures, see: Chandrasekhar et al. (2007[Chandrasekhar, V., Thilagar, P., Krishnan, V., Bickley, J. F. & Steiner, A. (2007). Cryst. Growth Des. 7, 668-675.]; 2011[Chandrasekhar, V., Pandey, M. D., Das, B., Mahanti, B., Gopal, K. & Azhakar, R. (2011). Tetrahedron, 67, 6917-6926.]; 2012[Chandrasekhar, V., Senapati, T., Dey, A., Das, S., Kalisz, M. & Clérac, R. (2012). Inorg. Chem. 51, 2031-2038.]); Harmjanz et al. (2004[Harmjanz, M., Piglosiewicz, I. M., Scott, B. L. & Burns, C. J. (2004). Inorg. Chem. 43, 642-650.]). For graph-set analysis, see: Etter (1990[Etter, M. C. (1990). Acc. Chem. Res. 23, 120-126.]). For ring asymmetry parameters, see: Duax et al. (1976[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.]).

[Scheme 1]

Experimental

Crystal data
  • C26H22N5O4P3·C3H6O

  • Mr = 619.47

  • Monoclinic, P 21 /c

  • a = 9.4901 (9) Å

  • b = 22.9466 (19) Å

  • c = 13.1776 (13) Å

  • [beta] = 97.978 (6)°

  • V = 2841.9 (5) Å3

  • Z = 4

  • Cu K[alpha] radiation

  • [mu] = 2.34 mm-1

  • T = 100 K

  • 0.19 × 0.12 × 0.03 mm

Data collection
  • Bruker Kappa APEXII DUO CCD diffractometer

  • Absorption correction: multi-scan (TWINABS; Sheldrick, 2004[Sheldrick, G. (2004). TWINABS. University of Göttingen, Germany.]) Tmin = 0.664, Tmax = 0.933

  • 33208 measured reflections

  • 5065 independent reflections

  • 4276 reflections with I > 2[sigma](I)

  • Rint = 0.051

Refinement
  • R[F2 > 2[sigma](F2)] = 0.037

  • wR(F2) = 0.102

  • S = 1.08

  • 5065 reflections

  • 387 parameters

  • H atoms treated by a mixture of independent and constrained refinement

  • [Delta][rho]max = 0.40 e Å-3

  • [Delta][rho]min = -0.39 e Å-3

Table 1
Hydrogen-bond geometry (Å, °)

D-H...A D-H H...A D...A D-H...A
N4-H4N...O5 0.82 (3) 2.22 (3) 2.991 (2) 158 (2)
N5-H5N...N3i 0.83 (3) 2.53 (3) 3.285 (2) 151 (2)
Symmetry code: (i) -x+2, -y+1, -z+1.

Data collection: APEX2 (Bruker, 2011[Bruker (2011). APEX2 and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.]); cell refinement: SAINT (Bruker, 2011[Bruker (2011). APEX2 and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.]); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); molecular graphics: ORTEP-3 for Windows (Farrugia, 2012[Farrugia, L. J. (2012). J. Appl. Cryst. 45, 849-854.]); software used to prepare material for publication: SHELXL97.


Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: JJ2173 ).


Acknowledgements

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.

References

Allcock, H. R. (1972). In Phosphorus-Nitrogen Compounds. New York: Academic Press, Inc.
Allen, C. W. (1991). Chem. Rev. 91, 119-135.  [CrossRef] [ChemPort] [ISI]
Bakos, D., Kosik, M., Antos, K., Karolyova, M. & Vyskocil, I. (1982). Fire Mater. 6, 10-11.  [ChemPort]
Barclay, T. M., Hicks, R. G., Ichimura, A. S. & Patenaude, G. W. (2002). Can. J. Chem. 80, 1501-1506.  [CrossRef] [ChemPort]
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.  [CrossRef] [ChemPort]
Chandrasekhar, V., Pandey, M. D., Das, B., Mahanti, B., Gopal, K. & Azhakar, R. (2011). Tetrahedron, 67, 6917-6926.  [CrossRef] [ChemPort]
Chandrasekhar, V., Senapati, T., Dey, A., Das, S., Kalisz, M. & Clérac, R. (2012). Inorg. Chem. 51, 2031-2038.  [CrossRef] [ChemPort] [PubMed]
Chandrasekhar, V., Thilagar, P., Krishnan, V., Bickley, J. F. & Steiner, A. (2007). Cryst. Growth Des. 7, 668-675.  [CrossRef] [ChemPort]
Ciftci, G. Y., Ecik, E. T., Yildirim, T., Bilgin, K., Senkuytu, E., Yuksel, F., Uludag, Y. & Kilic, A. (2013). Tetrahedron, 69, 1454-1461.  [ChemPort]
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.  [CrossRef] [ChemPort] [ISI]
Farrugia, L. J. (2012). J. Appl. Cryst. 45, 849-854.  [ISI] [CrossRef] [ChemPort] [details]
Harmjanz, M., Piglosiewicz, I. M., Scott, B. L. & Burns, C. J. (2004). Inorg. Chem. 43, 642-650.  [CrossRef] [PubMed] [ChemPort]
Olthof, R. (1969). Acta Cryst. B25, 2040-2045.  [CrossRef] [details]
Sheldrick, G. (2004). TWINABS. University of Göttingen, Germany.
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.  [CrossRef] [ChemPort] [details]


Acta Cryst (2013). E69, o1491-o1492   [ doi:10.1107/S1600536813023830 ]

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