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Volume 70 
Part 1 
Page o3  
January 2014  

Received 15 November 2013
Accepted 28 November 2013
Online 4 December 2013

Key indicators
Single-crystal X-ray study
T = 293 K
Mean [sigma](C-C) = 0.003 Å
R = 0.043
wR = 0.127
Data-to-parameter ratio = 32.2
Details
Open access

Bis(benzyl­ammonium) di­hydrogen diphosphate

aLaboratoire de Chimie des Matériaux, Faculté des Sciences de Bizerte, 7021 Zarzouna Bizerte, Tunisia, and bCEMES-CNRS, 29 rue Jeanne Marvig, 31055 Toulouse cedex 4, France
Correspondence e-mail: samah.akriche@fsb.rnu.tn

The asymmetric unit of the title salt, 2C6H5CH2NH3+·H2P2O72-, contains two independent benzyl­ammonium cations and a di­hydrogen diphosphate dianion. In the crystal, O-H...O and N-H...O hydrogen bonds link the cations and anions, forming a two-dimensional network parallel to (010). Within this network, weak C-H...O hydrogen bonds are observed.

Related literature

For the chemistry of diphosphate materials, see: Ernester (1992[Ernester, L. (1992). In Molecular Mechanism in Bioenergetics. Amsterdam: Elsevier.]); Lipscomb & Strater (1996[Lipscomb, W. N. & Strater, N. (1996). Chem. Rev. 96, 2375-2433.]); Centi et al. (1988[Centi, G., Trifirò, F., Ebner, J. R. & Franchetti, V. M. (1988). Chem. Rev. 88, 55-80.]); Chen & Munson (2002[Chen, B. & Munson, E. J. (2002). J. Am. Chem. Soc. 124, 1638-1652.]); Ballarini et al. (2006[Ballarini, N., Cavani, F., Cortelli, C., Ligi, S., Pierelli, F., Trifiro, F., Fumagalli, C., Mazzoni, G. & Monti, T. (2006). Top. Catal. 38, 147-156.]). For details of hydrogen bonds, see: Desiraju (1991[Desiraju, G. R. (1991). Acc. Chem. Res. 24, 290-296.]); Steiner (2002[Steiner, T. (2002). Angew. Chem. Int. Ed. 41, 48-76.]). For related structures, see: Akriche & Rzaigui (2005[Akriche, S. & Rzaigui, M. (2005). Acta Cryst. E61, o2607-o2609.], 2008[Akriche, S. & Rzaigui, M. (2008). Struct. Chem. 19, 827-831.]); Ahmed et al. (2006[Ahmed, S., Samah, A. & Mohamed, R. (2006). Acta Cryst. E62, m1796-m1798.]); Elboulali et al. (2013[Elboulali, A., Akriche, S., Al-Deyab, S. S. & Rzaigui, M. (2013). Acta Cryst. E69, o213-o214.]).

[Scheme 1]

Experimental

Crystal data
  • 2C7H10N+·H2P2O72-

  • Mr = 392.27

  • Monoclinic, P 21 /c

  • a = 8.1337 (2) Å

  • b = 28.9015 (9) Å

  • c = 8.4727 (2) Å

  • [beta] = 113.449 (1)°

  • V = 1827.24 (9) Å3

  • Z = 4

  • Mo K[alpha] radiation

  • [mu] = 0.28 mm-1

  • T = 293 K

  • 0.3 × 0.2 × 0.1 mm

Data collection
  • Nonius KappaCCD diffractometer

  • 27919 measured reflections

  • 7410 independent reflections

  • 5946 reflections with I > 2[sigma](I)

  • Rint = 0.025

Refinement
  • R[F2 > 2[sigma](F2)] = 0.043

  • wR(F2) = 0.127

  • S = 1.06

  • 7410 reflections

  • 230 parameters

  • H-atom parameters constrained

  • [Delta][rho]max = 0.52 e Å-3

  • [Delta][rho]min = -0.28 e Å-3

Table 1
Hydrogen-bond geometry (Å, °)

D-H...A D-H H...A D...A D-H...A
O1-H1O1...O6i 0.82 1.90 2.7208 (13) 174
O5-H5O5...O3ii 0.82 1.83 2.6061 (13) 158
N1-H1N1...O2 0.89 2.07 2.9292 (13) 162
N1-H2N1...O6iii 0.89 2.10 2.9698 (15) 166
N1-H2N1...O4iii 0.89 2.53 3.1493 (13) 127
N1-H3N1...O7iv 0.89 1.88 2.7645 (15) 169
N2-H1N2...O3ii 0.89 1.94 2.7956 (15) 160
N2-H2N2...O2 0.89 1.98 2.8637 (15) 169
N2-H3N2...O6iii 0.89 1.99 2.8053 (14) 152
C1-H1B...O5ii 0.97 2.52 3.3333 (19) 141
C8-H8B...O7 0.97 2.40 3.1558 (17) 135
Symmetry codes: (i) -x+1, -y, -z+2; (ii) -x, -y, -z+1; (iii) x-1, y, z; (iv) -x, -y, -z+2.

Data collection: COLLECT (Hooft, 1998[Hooft, R. W. W. (1998). COLLECT. Nonius BV, Delft, The Netherlands.]); cell refinement: DIRAX/LSQ (Duisenberg et al., 2000[Duisenberg, A. J. M., Hooft, R. W. W., Schreurs, A. M. M. & Kroon, J. (2000). J. Appl. Cryst. 33, 893-898.]); data reduction: EVALCCD (Duisenberg et al., 2003[Duisenberg, A. J. M., Kroon-Batenburg, L. M. J. & Schreurs, A. M. M. (2003). J. Appl. Cryst. 36, 220-229.]); 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.]) and DIAMOND (Brandenburg & Putz, 2005[Brandenburg, K. & Putz, H. (2005). DIAMOND. Crystal Impact GbR, Bonn, Germany.]); software used to prepare material for publication: WinGX publication routines (Farrugia, 2012[Farrugia, L. J. (2012). J. Appl. Cryst. 45, 849-854.]).


Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: LH5670 ).


References

Ahmed, S., Samah, A. & Mohamed, R. (2006). Acta Cryst. E62, m1796-m1798.  [CSD] [CrossRef] [ChemPort] [IUCr Journals]
Akriche, S. & Rzaigui, M. (2005). Acta Cryst. E61, o2607-o2609.  [CSD] [CrossRef] [ChemPort] [IUCr Journals]
Akriche, S. & Rzaigui, M. (2008). Struct. Chem. 19, 827-831.  [Web of Science] [CSD] [CrossRef] [ChemPort]
Ballarini, N., Cavani, F., Cortelli, C., Ligi, S., Pierelli, F., Trifiro, F., Fumagalli, C., Mazzoni, G. & Monti, T. (2006). Top. Catal. 38, 147-156.  [Web of Science] [CrossRef] [ChemPort]
Brandenburg, K. & Putz, H. (2005). DIAMOND. Crystal Impact GbR, Bonn, Germany.
Centi, G., Trifirò, F., Ebner, J. R. & Franchetti, V. M. (1988). Chem. Rev. 88, 55-80.  [CrossRef] [ChemPort] [Web of Science]
Chen, B. & Munson, E. J. (2002). J. Am. Chem. Soc. 124, 1638-1652.  [Web of Science] [CrossRef] [PubMed] [ChemPort]
Desiraju, G. R. (1991). Acc. Chem. Res. 24, 290-296.  [CrossRef] [ChemPort] [Web of Science]
Duisenberg, A. J. M., Hooft, R. W. W., Schreurs, A. M. M. & Kroon, J. (2000). J. Appl. Cryst. 33, 893-898.  [Web of Science] [CrossRef] [ChemPort] [IUCr Journals]
Duisenberg, A. J. M., Kroon-Batenburg, L. M. J. & Schreurs, A. M. M. (2003). J. Appl. Cryst. 36, 220-229.  [Web of Science] [CrossRef] [ChemPort] [IUCr Journals]
Elboulali, A., Akriche, S., Al-Deyab, S. S. & Rzaigui, M. (2013). Acta Cryst. E69, o213-o214.  [CSD] [CrossRef] [ChemPort] [IUCr Journals]
Ernester, L. (1992). In Molecular Mechanism in Bioenergetics. Amsterdam: Elsevier.
Farrugia, L. J. (2012). J. Appl. Cryst. 45, 849-854.  [Web of Science] [CrossRef] [ChemPort] [IUCr Journals]
Hooft, R. W. W. (1998). COLLECT. Nonius BV, Delft, The Netherlands.
Lipscomb, W. N. & Strater, N. (1996). Chem. Rev. 96, 2375-2433.  [CrossRef] [PubMed] [ChemPort] [Web of Science]
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.  [CrossRef] [ChemPort] [IUCr Journals]
Steiner, T. (2002). Angew. Chem. Int. Ed. 41, 48-76.  [Web of Science] [CrossRef] [ChemPort]


Acta Cryst (2014). E70, o3  [ doi:10.1107/S1600536813032455 ]

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