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Volume 69 
Part 6 
Pages o994-o995  
June 2013  

Received 16 May 2013
Accepted 22 May 2013
Online 31 May 2013

Key indicators
Single-crystal X-ray study
T = 100 K
Mean [sigma](C-C) = 0.002 Å
R = 0.040
wR = 0.109
Data-to-parameter ratio = 19.9
Details
Open access

2-(4-Methylpyridin-2-yl)-4',4',6',6'-tetrakis(pyrrolidin-1-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

In the title spiro-phosphazene derivative, C33H46N9OP3, the phosphazene and six-membered N/O rings are in flattened chair and twisted-boat conformations, respectively. The naphthalene ring system and the pyridine ring are oriented at a dihedral angle of 41.82 (4)°. In the crystal, weak C-H...O hydrogen bonds link the molecules related by translation along the a axis into chains. C-H...[pi] interactions aggregate these chains into layers parallel to the ab plane.

Related literature

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.]); 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.], 2013[Isiklan, M., Sonkaya, Ö. & Hökelek, T. (2013). Acta Cryst. E69, o861-o862.]). 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
  • C33H46N9OP3

  • Mr = 677.70

  • Triclinic, [P \overline 1]

  • a = 9.5830 (2) Å

  • b = 10.9142 (2) Å

  • c = 16.8172 (3) Å

  • [alpha] = 79.210 (2)°

  • [beta] = 84.542 (3)°

  • [gamma] = 74.193 (2)°

  • V = 1660.68 (6) Å3

  • Z = 2

  • Mo K[alpha] radiation

  • [mu] = 0.22 mm-1

  • T = 100 K

  • 0.31 × 0.26 × 0.25 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 = 0.934, Tmax = 0.947

  • 30003 measured reflections

  • 8270 independent reflections

  • 6876 reflections with I > 2[sigma](I)

  • Rint = 0.030

Refinement
  • R[F2 > 2[sigma](F2)] = 0.040

  • wR(F2) = 0.109

  • S = 1.04

  • 8270 reflections

  • 416 parameters

  • H-atom parameters constrained

  • [Delta][rho]max = 0.89 e Å-3

  • [Delta][rho]min = -0.37 e Å-3

Table 1
Hydrogen-bond geometry (Å, °)

Cg1 is the centroid of the C1-C6 ring.

D-H...A D-H H...A D...A D-H...A
C17-H17A...O1i 0.96 2.47 3.372 (2) 156
C24-H24B...Cg1ii 0.97 2.74 3.624 (2) 152
Symmetry codes: (i) x+1, y, z; (ii) x, y+1, z.

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: CV5414 ).


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

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.
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]
Farrugia, L. J. (2012). J. Appl. Cryst. 45, 849-854.  [ISI] [CrossRef] [ChemPort] [details]
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]
Isiklan, M., Sonkaya, Ö. & Hökelek, T. (2013). Acta Cryst. E69, o861-o862.  [CrossRef] [details]
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.  [CrossRef] [ChemPort] [details]
Spek, A. L. (2009). Acta Cryst. D65, 148-155.  [ISI] [CrossRef] [ChemPort] [details]


Acta Cryst (2013). E69, o994-o995   [ doi:10.1107/S1600536813014220 ]

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