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Volume 69 
Part 6 
Pages o861-o862  
June 2013  

Received 3 May 2013
Accepted 6 May 2013
Online 11 May 2013

Key indicators
Single-crystal X-ray study
T = 100 K
Mean [sigma](C-C) = 0.005 Å
R = 0.048
wR = 0.129
Data-to-parameter ratio = 19.5
Details
Open access

4',4',6',6'-Tetrachloro-2-(6-methylpyridin-2-yl)-1H,2H-spiro[naphtho[1,2-e][1,3,2]oxazaphosphinine-3,2'-[1,3,5,2,4,6]triazatriphosphinine]

aDepartment of Chemistry, Kirikkale University, 71450, Kirikkale, Turkey, and bDepartment of Physics, Hacettepe University, 06800 Beytepe, Ankara, Turkey
Correspondence e-mail: merzifon@hacettepe.edu.tr

The title compound, C17H14Cl4N5OP3, is a spiro-phosphazene derivative with bulky naphthalene and pyridine rings. The phosphazene and the six-membered N/O rings are in flattened-boat and twisted-boat conformations, respectively. The naphthalene ring system and the pyridine ring are oriented at a dihedral angle of 18.06 (8)°. In the crystal, weak [pi]-[pi] stacking between the pyridine rings and between the pyridine rings and the naphthalene ring system [centroid-centroid distances = 3.594 (2) and 3.961 (2) Å, respectively] occur. Weak C-H...[pi] interactions are also observed. These interactions link the molecules into a three-dimensional supramolecular network.

Related literature

For products from the reaction of N3P3Cl6 with bifunctional reagents, see: Besli et al. (2006[Besli, S., Coles, S. J., Davies, D. B., Eaton, R. J., Kiliç, A. & Shaw, R. A. (2006). Polyhedron, 25, 963-974.]). For N/O donor type bifunctional reagents used for the reaction of hexachlorocyclotriphosphazene giving spiro derivatives, see: Besli et al. (2007[Besli, S., Coles, S. J., Davies, D. B., Hursthouse, M. B., Kiliç, A. & Shaw, R. A. (2007). Dalton Trans. pp. 2792-2801.]); Sournies et al. (1997[Sournies, F., Zai, K., Vercruysse, K., Labarre, M. C. & Labarre, J. F. (1997). J. Mol. Struct. 412, 19-26.]); Deutsch & Shaw (1990[Deutsch, W. F. & Shaw, R. A. (1990). Phosphorus Sulfur Silicon, 47, 119-140.]); Isiklan et al. (2010[Isiklan, M., Asmafiliz, N., Özalp, E. E., Ilter, E. E., Kiliç, Z., Cosut, B., Yesilot, S., Kiliç, A., Öztürk, A., Hökelek, T., Koç, L. Y., Açik, L. & Akyüz, E. (2010). Inorg. Chem. 49, 7057-7071.]); Ilter et al. (2004[Ilter, E. E., Çaylak, N., Isiklan, M., Asmafiliz, N., Kiliç, Z. & Hökelek, T. (2004). J. Mol. Struct. 697, 119-129.], 2007[Ilter, E. E., Asmafiliz, N., Kiliç, Z., Isiklan, M., Hökelek, T., Çaylak, N. & Sahin, E. (2007). Inorg. Chem. 46, 9931-9944.]); Tercan et al. (2004[Tercan, B., Hökelek, T., Isiklan, M., Ilter, E. E. & Kiliç, Z. (2004). Acta Cryst. E60, o971-o973.]). For industrial applications of cyclophosphazenes, see: Omotowa et al. (2004[Omotowa, B. A., Phillips, B. S., Zabinski, J. S. & Shreeve, J. M. (2004). Inorg. Chem. 43, 5466-5471.]); Barbera et al. (2005[Barbera, J., Bardaji, M., Jimenez, J., Laguna, A., Martinez, M. P., Oriol, L., Serrano, J. L. & Zaragozano, I. (2005). J. Am. Chem. Soc. 127, 8994-9002.]); Schneider et al. (1999[Schneider, R., Köllner, C., Weber, I. & Togni, A. (1999). Chem. Commun. 23, 2415-2416.]); Ding et al. (2005[Ding, J., Liang, H., Shi, W. & Shen, X. (2005). J. Appl. Polym. Sci. 97, 1776-1782.]); Allcock (2006[Allcock, H. R. (2006). Curr. Opin. Solid State Mater. Sci. 10, 231-240.]); Xu et al. (2006[Xu, G.-X., Lu, Q., Yu, B. T. & Wen, L. (2006). Solid State Ionics, 177, 305-309.]); Allcock & Wood (2006[Allcock, H. R. & Wood, R. M. (2006). J. Polym. Sci. Part B Polym. Phys. 44, 2358-2368.]); Li et al. (2004[Li, Z., Huang, C., Hua, J., Qin, J., Yang, Z. & Ye, C. (2004). Macromolecules, 37, 371-376.]); Singh et al. (2006[Singh, A., Krogman, N. R., Sethurman, S., Nair, L. S., Sturgeon, J. L., Brown, P. W., Laurencin, C. T. & Allcock, H. R. (2006). Biomacromolecules, 7, 914-918.]); Greish et al. (2005[Greish, Y. E., Bender, J. E., Lakshmi, S., Brown, P. W., Allcock, H. R. & Laurencin, C. T. (2005). Biomaterials, 26, 1-9.]). For bond-length data, see: Allen et al. (1987[Allen, F. H., Kennard, O., Watson, D. G., Brammer, L., Orpen, A. G. & Taylor, R. (1987). J. Chem. Soc. Perkin Trans. 2, pp. S1-19.]). For the standard compound, N3P3Cl6, see: Bullen (1971[Bullen, G. J. (1971). J. Chem. Soc. A, pp. 1450-1453.]). For ring-puckering parameters, see: Cremer & Pople (1975[Cremer, D. & Pople, J. A. (1975). J. Am. Chem. Soc. 97, 1354-1358.]).

[Scheme 1]

Experimental

Crystal data
  • C17H14Cl4N5OP3

  • Mr = 539.04

  • Orthorhombic, P b c a

  • a = 21.7784 (5) Å

  • b = 7.8573 (3) Å

  • c = 25.1034 (5) Å

  • V = 4295.7 (2) Å3

  • Z = 8

  • Mo K[alpha] radiation

  • [mu] = 0.80 mm-1

  • T = 100 K

  • 0.38 × 0.28 × 0.08 mm

Data collection
  • Bruker Kappa APEXII CCD area-detector diffractometer

  • Absorption correction: multi-scan (SADABS; Bruker, 2005[Bruker (2005). SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.]) Tmin = 0.752, Tmax = 0.939

  • 22083 measured reflections

  • 5297 independent reflections

  • 3446 reflections with I > 2[sigma](I)

  • Rint = 0.070

Refinement
  • R[F2 > 2[sigma](F2)] = 0.048

  • wR(F2) = 0.129

  • S = 1.01

  • 5297 reflections

  • 272 parameters

  • H-atom parameters constrained

  • [Delta][rho]max = 0.73 e Å-3

  • [Delta][rho]min = -0.77 e Å-3

Table 1
Selected bond lengths (Å)

P1-O1 1.580 (2)
P1-N1 1.596 (3)
P1-N3 1.598 (3)
P1-N4 1.665 (3)
P2-N1 1.571 (3)
P2-N2 1.580 (3)
P3-N2 1.581 (3)
P3-N3 1.571 (3)

Table 2
Hydrogen-bond geometry (Å, °)

Cg3 is the centroid of the C8-benzene ring.

D-H...A D-H H...A D...A D-H...A
C7-H7...Cg3i 0.95 2.82 3.507 (3) 130
Symmetry code: (i) [x, -y-{\script{1\over 2}}, z-{\script{1\over 2}}].

Data collection: APEX2 (Bruker, 2007[Bruker (2007). APEX2 and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.]); cell refinement: SAINT (Bruker, 2007[Bruker (2007). 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: WinGX (Farrugia, 2012[Farrugia, L. J. (2012). J. Appl. Cryst. 45, 849-854.]) and PLATON (Spek, 2009[Spek, A. L. (2009). Acta Cryst. D65, 148-155.]).


Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: XU5701 ).


Acknowledgements

The authors are indebted to Anadolu University and the Medicinal Plants and Medicine Research Centre of Anadolu University, Eskisehir, Turkey, for the use of X-ray diffractometer. The authors gratefully acknowledge the Kirikkale University Scientific Research Projects Coordination Unit (grant No. 2009/42), the Scientific and Technical Research Council of Turkey, TÜBITAK (grant No. 106 T503) and the Hacettepe University Scientific Research Unit (grant No. 02 02 602 002) for financial support.

References

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Allcock, H. R. & Wood, R. M. (2006). J. Polym. Sci. Part B Polym. Phys. 44, 2358-2368.  [ISI] [CrossRef] [ChemPort]
Allen, F. H., Kennard, O., Watson, D. G., Brammer, L., Orpen, A. G. & Taylor, R. (1987). J. Chem. Soc. Perkin Trans. 2, pp. S1-19.
Barbera, J., Bardaji, M., Jimenez, J., Laguna, A., Martinez, M. P., Oriol, L., Serrano, J. L. & Zaragozano, I. (2005). J. Am. Chem. Soc. 127, 8994-9002.  [ISI] [PubMed] [ChemPort]
Besli, S., Coles, S. J., Davies, D. B., Eaton, R. J., Kiliç, A. & Shaw, R. A. (2006). Polyhedron, 25, 963-974.
Besli, S., Coles, S. J., Davies, D. B., Hursthouse, M. B., Kiliç, A. & Shaw, R. A. (2007). Dalton Trans. pp. 2792-2801.
Bruker (2005). SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.
Bruker (2007). APEX2 and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.
Bullen, G. J. (1971). J. Chem. Soc. A, pp. 1450-1453.
Cremer, D. & Pople, J. A. (1975). J. Am. Chem. Soc. 97, 1354-1358.  [CrossRef] [ChemPort] [ISI]
Deutsch, W. F. & Shaw, R. A. (1990). Phosphorus Sulfur Silicon, 47, 119-140.  [CrossRef] [ChemPort]
Ding, J., Liang, H., Shi, W. & Shen, X. (2005). J. Appl. Polym. Sci. 97, 1776-1782.  [ISI] [CrossRef] [ChemPort]
Farrugia, L. J. (2012). J. Appl. Cryst. 45, 849-854.  [ISI] [CrossRef] [ChemPort] [details]
Greish, Y. E., Bender, J. E., Lakshmi, S., Brown, P. W., Allcock, H. R. & Laurencin, C. T. (2005). Biomaterials, 26, 1-9.  [ISI] [CrossRef] [PubMed] [ChemPort]
Ilter, E. E., Asmafiliz, N., Kiliç, Z., Isiklan, M., Hökelek, T., Çaylak, N. & Sahin, E. (2007). Inorg. Chem. 46, 9931-9944.  [PubMed]
Ilter, E. E., Çaylak, N., Isiklan, M., Asmafiliz, N., Kiliç, Z. & Hökelek, T. (2004). J. Mol. Struct. 697, 119-129.
Isiklan, M., Asmafiliz, N., Özalp, E. E., Ilter, E. E., Kiliç, Z., Cosut, B., Yesilot, S., Kiliç, A., Öztürk, A., Hökelek, T., Koç, L. Y., Açik, L. & Akyüz, E. (2010). Inorg. Chem. 49, 7057-7071.  [ISI] [PubMed]
Li, Z., Huang, C., Hua, J., Qin, J., Yang, Z. & Ye, C. (2004). Macromolecules, 37, 371-376.  [ISI] [CrossRef] [ChemPort]
Omotowa, B. A., Phillips, B. S., Zabinski, J. S. & Shreeve, J. M. (2004). Inorg. Chem. 43, 5466-5471.  [ISI] [CrossRef] [PubMed] [ChemPort]
Schneider, R., Köllner, C., Weber, I. & Togni, A. (1999). Chem. Commun. 23, 2415-2416.  [CrossRef]
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.  [CrossRef] [ChemPort] [details]
Singh, A., Krogman, N. R., Sethurman, S., Nair, L. S., Sturgeon, J. L., Brown, P. W., Laurencin, C. T. & Allcock, H. R. (2006). Biomacromolecules, 7, 914-918.  [ISI] [CrossRef] [PubMed] [ChemPort]
Sournies, F., Zai, K., Vercruysse, K., Labarre, M. C. & Labarre, J. F. (1997). J. Mol. Struct. 412, 19-26.  [CrossRef] [ChemPort] [ISI]
Spek, A. L. (2009). Acta Cryst. D65, 148-155.  [ISI] [CrossRef] [ChemPort] [details]
Tercan, B., Hökelek, T., Isiklan, M., Ilter, E. E. & Kiliç, Z. (2004). Acta Cryst. E60, o971-o973.  [CSD] [CrossRef] [ChemPort] [details]
Xu, G.-X., Lu, Q., Yu, B. T. & Wen, L. (2006). Solid State Ionics, 177, 305-309.  [ISI] [CrossRef] [ChemPort]


Acta Cryst (2013). E69, o861-o862   [ doi:10.1107/S1600536813012348 ]

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