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Volume 69 
Part 8 
Pages m464-m465  
August 2013  

Received 13 June 2013
Accepted 11 July 2013
Online 20 July 2013

Key indicators
Single-crystal X-ray study
T = 100 K
Mean [sigma](C-C) = 0.001 Å
R = 0.030
wR = 0.090
Data-to-parameter ratio = 31.1
Details
Open access

Poly[[[mu]-bis(4-nitrophenyl) phosphato-[kappa]2O,O']sodium]

aUniversity of Wroclaw, Faculty of Chemistry, 14 Joliot-Curie St, 50-383 Wroclaw, Poland
Correspondence e-mail: aleksandra.gerus@chem.uni.wroc.pl

The title compound, [Na(C12H8N2O8P)], consists of one Na+ cation and one bis(p-nitrophenyl)phosphate anion with a considerable distortion of the phosphate tetrahedron due to the presence of two P-O ester bonds. The anion bridges five Na+ cations whereby each cation is chelated by the nitro O atoms of one anion and bonded via a nitro O atom and phosphate O atoms to four other anions. This bridging arrangement leads to the formation of double layers parallel to (001). Adjacent layers are linked through weak C-H...O hydrogen bonds.

Related literature

For hydrolytic cleavage of the phosphodiester bond in bis(p-nitrophenyl)phosphate (BNPP) and related systems, see: Belousoff et al. (2009[Belousoff, M. J., Ung, P., Forsyth, C. M., Tor, Y., Spiccia, L. & Graham, B. (2009). J. Am. Chem. Soc. 131, 1106-1114.]); Branum et al. (2001[Branum, M. E., Tipton, A. K., Zhu, S. & Que, L. (2001). J. Am. Chem. Soc. 123, 1898-1904.]); Chang et al. (2009[Chang, C. A., Wu, B. H. & Hsiao, C.-H. (2009). Eur. J. Inorg. Chem. pp. 1339-1346.]); Liu et al. (2004[Liu, C., Wang, M., Zhang, T. & Sun, H. (2004). Coord. Chem. Rev. 248, 147-168.]); Mancin et al. (2005[Mancin, F., Scrimin, P., Tecilla, P. & Tonellato, U. (2005). Chem. Commun. pp. 2540-2548.]); Oh et al. (1996[Oh, S. J., Song, K. H., Whang, D., Kim, K., Yoon, T. H., Moon, H. & Park, J. W. (1996). Inorg. Chem. 35, 3780-3785.]); Sredhera & Cowan (2001[Sredhera, A. & Cowan, J. A. (2001). J. Biol. Inorg. Chem. 6, 337-347.]). For crystal structures containing the BNPP entity, see: Bazzicalupi et al. (2004[Bazzicalupi, C., Bencini, A., Berni, E., Bianchi, A., Fornasari, P., Giorgi, C. & Valtancoli, B. (2004). Inorg. Chem. 43, 6255-6265.]); Bond et al. (1985[Bond, D. R., Modro, T. A. & Nassimbeni, L. R. (1985). J. Org. Chem. 50, 2281-2287.]); Fry et al. (2003[Fry, F. H., Jensen, P., Kepert, C. M. & Spiccia, L. (2003). Inorg. Chem. 42, 5637-5644.]); Jurek & Martell (1999[Jurek, P. E. & Martell, A. E. (1999). Inorg. Chem. 38, 6003-6007.]); Král et al. (2006[Král, V., Lang, K., Králová, J., Dvorák, M., Martásek, P., Chin, A. O., Andrievsky, A., Lynch, V. & Sessler, J. L. (2006). J. Am. Chem. Soc. 128, 432-437.]); Pletcher et al. (1972[Pletcher, J., Sax, M. & Yoo, C. S. (1972). Acta Cryst. B28, 378-387.]); Sax et al. (1970[Sax, M., Pletcher, J. & Gustaffson, B. (1970). Acta Cryst. B26, 114-124.], 1971[Sax, M., Pletcher, J., Yoo, C. S. & Stewart, J. M. (1971). Acta Cryst. B27, 1635-1644.]); Warden et al. (2005[Warden, A. C., Warren, M., Hearn, M. T. W. & Spiccia, L. (2005). Cryst. Growth Des. 5, 713-720.]); Yoo et al. (1975[Yoo, C. S., Abola, E., Wood, M. K., Sax, M. & Pletcher, J. (1975). Acta Cryst. B31, 1354-1360.]).

[Scheme 1]

Experimental

Crystal data
  • [Na(C12H8N2O8P)]

  • Mr = 362.16

  • Triclinic, [P \overline 1]

  • a = 6.963 (2) Å

  • b = 9.844 (3) Å

  • c = 11.213 (3) Å

  • [alpha] = 103.93 (3)°

  • [beta] = 105.83 (3)°

  • [gamma] = 106.38 (3)°

  • V = 666.1 (3) Å3

  • Z = 2

  • Mo K[alpha] radiation

  • [mu] = 0.29 mm-1

  • T = 100 K

  • 0.30 × 0.27 × 0.25 mm

Data collection
  • Agilent Xcalibur (Onyx with CCD camera) diffractometer

  • Absorption correction: analytical (CrysAlis PRO; Agilent, 2011[Agilent (2011). CrysAlis PRO. Agilent Technologies, Yarnton, England.]) Tmin = 0.918, Tmax = 0.931

  • 13418 measured reflections

  • 6748 independent reflections

  • 5542 reflections with I > 2[sigma](I)

  • Rint = 0.014

Refinement
  • R[F2 > 2[sigma](F2)] = 0.030

  • wR(F2) = 0.090

  • S = 1.07

  • 6748 reflections

  • 217 parameters

  • H-atom parameters constrained

  • [Delta][rho]max = 0.66 e Å-3

  • [Delta][rho]min = -0.33 e Å-3

Table 1
Selected geometric parameters (Å, °)

P1-O31 1.4733 (8)
P1-O41 1.4834 (7)
P1-O11 1.6266 (8)
P1-O21 1.6287 (12)
O1-Na 2.9377 (18)
O2-Na 2.4618 (11)
O4-Nai 2.3853 (11)
O31-Naii 2.2386 (10)
O41-Naiii 2.3135 (9)
O41-Naiv 2.4065 (14)
O31-P1-O41 119.67 (5)
O31-P1-O11 110.86 (4)
O41-P1-O11 110.02 (4)
O31-P1-O21 110.48 (5)
O41-P1-O21 110.21 (4)
O11-P1-O21 92.20 (4)
Symmetry codes: (i) x-1, y-2, z; (ii) x, y-1, z; (iii) x-1, y-1, z; (iv) -x+1, -y+2, -z+1.

Table 2
Hydrogen-bond geometry (Å, °)

D-H...A D-H H...A D...A D-H...A
C2-H2...O3v 0.95 2.50 3.1865 (15) 129
C21-H21...O1vi 0.95 2.53 3.3337 (18) 142
Symmetry codes: (v) -x, -y, -z; (vi) -x, -y+1, -z.

Data collection: CrysAlis PRO (Agilent, 2011[Agilent (2011). CrysAlis PRO. Agilent Technologies, Yarnton, England.]); cell refinement: CrysAlis PRO; data reduction: CrysAlis PRO; 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: XP in SHELXTL (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); software used to prepare material for publication: publCIF (Westrip, 2010[Westrip, S. P. (2010). J. Appl. Cryst. 43, 920-925.]).


Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: WM2751 ).


Acknowledgements

We thank Professor Dr Jerzy Lisowski for helpful discussions during preparation of this article.

References

Agilent (2011). CrysAlis PRO. Agilent Technologies, Yarnton, England.
Bazzicalupi, C., Bencini, A., Berni, E., Bianchi, A., Fornasari, P., Giorgi, C. & Valtancoli, B. (2004). Inorg. Chem. 43, 6255-6265.  [Web of Science] [CSD] [CrossRef] [PubMed] [ChemPort]
Belousoff, M. J., Ung, P., Forsyth, C. M., Tor, Y., Spiccia, L. & Graham, B. (2009). J. Am. Chem. Soc. 131, 1106-1114.  [Web of Science] [CSD] [CrossRef] [PubMed] [ChemPort]
Bond, D. R., Modro, T. A. & Nassimbeni, L. R. (1985). J. Org. Chem. 50, 2281-2287.  [CrossRef] [ChemPort]
Branum, M. E., Tipton, A. K., Zhu, S. & Que, L. (2001). J. Am. Chem. Soc. 123, 1898-1904.  [Web of Science] [CrossRef] [PubMed] [ChemPort]
Chang, C. A., Wu, B. H. & Hsiao, C.-H. (2009). Eur. J. Inorg. Chem. pp. 1339-1346.  [Web of Science] [CrossRef]
Fry, F. H., Jensen, P., Kepert, C. M. & Spiccia, L. (2003). Inorg. Chem. 42, 5637-5644.  [Web of Science] [CSD] [CrossRef] [PubMed] [ChemPort]
Jurek, P. E. & Martell, A. E. (1999). Inorg. Chem. 38, 6003-6007.  [Web of Science] [CSD] [CrossRef] [PubMed] [ChemPort]
Král, V., Lang, K., Králová, J., Dvorák, M., Martásek, P., Chin, A. O., Andrievsky, A., Lynch, V. & Sessler, J. L. (2006). J. Am. Chem. Soc. 128, 432-437.  [Web of Science] [PubMed]
Liu, C., Wang, M., Zhang, T. & Sun, H. (2004). Coord. Chem. Rev. 248, 147-168.  [Web of Science] [CrossRef] [ChemPort]
Mancin, F., Scrimin, P., Tecilla, P. & Tonellato, U. (2005). Chem. Commun. pp. 2540-2548.  [CrossRef]
Oh, S. J., Song, K. H., Whang, D., Kim, K., Yoon, T. H., Moon, H. & Park, J. W. (1996). Inorg. Chem. 35, 3780-3785.  [CrossRef] [PubMed] [ChemPort] [Web of Science]
Pletcher, J., Sax, M. & Yoo, C. S. (1972). Acta Cryst. B28, 378-387.  [CrossRef] [ChemPort] [IUCr Journals]
Sax, M., Pletcher, J. & Gustaffson, B. (1970). Acta Cryst. B26, 114-124.  [CrossRef] [ChemPort] [IUCr Journals]
Sax, M., Pletcher, J., Yoo, C. S. & Stewart, J. M. (1971). Acta Cryst. B27, 1635-1644.  [CrossRef] [ChemPort] [IUCr Journals]
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.  [CrossRef] [ChemPort] [IUCr Journals]
Sredhera, A. & Cowan, J. A. (2001). J. Biol. Inorg. Chem. 6, 337-347.  [Web of Science] [PubMed]
Warden, A. C., Warren, M., Hearn, M. T. W. & Spiccia, L. (2005). Cryst. Growth Des. 5, 713-720.  [CSD] [CrossRef] [ChemPort]
Westrip, S. P. (2010). J. Appl. Cryst. 43, 920-925.  [Web of Science] [CrossRef] [ChemPort] [IUCr Journals]
Yoo, C. S., Abola, E., Wood, M. K., Sax, M. & Pletcher, J. (1975). Acta Cryst. B31, 1354-1360.  [CrossRef] [IUCr Journals]


Acta Cryst (2013). E69, m464-m465   [ doi:10.1107/S1600536813019260 ]

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