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Volume 69 
Part 2 
Pages o159-o160  
February 2013  

Received 1 December 2012
Accepted 20 December 2012
Online 4 January 2013

Key indicators
Single-crystal X-ray study
T = 100 K
Mean [sigma](C-C) = 0.002 Å
Disorder in main residue
R = 0.025
wR = 0.064
Data-to-parameter ratio = 22.2
Details
Open access

2-Chlorobenzene-1,4-diaminium bis(dihydrogenphosphate)

aLaboratoire de Chimie des Matériaux, Faculté des Sciences de Bizerte, 7021 Zarzouna, Tunisia, and bDepartment of Chemistry, Youngstown State University, One University Plaza, Youngstown, Ohio 44555-3663, USA
Correspondence e-mail: cherif_bennasr@yahoo.fr

The asymmetric unit of the title salt, C6H9ClN22+·2H2PO4-, contains two dihydrogenphosphate anions and one 2-chlorobenzene-1,4-diaminium dication. The H2PO4- anions are interconnected through strong O-H...O hydrogen bonds to form two-dimensional infinite layers parallel to (001). The organic entities are anchored to the inorganic layers through N-H...O hydrogen bonds, and through weak C-Cl...O halogen bonds [3.159 (2) Å, 140.48 (7)°]. No [pi]-[pi] stacking interactions between neighboring aromatic rings or C-H...[pi] interactions towards them are observed. Minor disorder is observed for the Cl atom and one hydroxy group [minor-component occupancy = 3.29 (9)%].

Related literature

For common applications of organic phosphate complexes, see: Masse et al. (1993[Masse, R., Bagieu-Beucher, M., Pecaut, J., Levy, J. P. & Zyss, J. (1993). Nonlinear Opt. 5, 413-423.]). For network geometries, see: Rayes et al. (2004[Rayes, A., Ben Nasr, C. & Rzaigui, M. (2004). Mater. Res. Bull. 39, 1113-1121.]); Oueslati et al. (2005[Oueslati, A., Ben Nasr, C., Durif, A. & Lefebvre, F. (2005). Mater. Res. Bull. 39, 970-980.]). For reference structural data, see: Kaabi et al. (2004[Kaabi, K., Ben Nasr, C. & Lefebvre, F. (2004). Mater. Res. Bull. 39, 205-215.]); Chtioui & Jouini (2006[Chtioui, A. & Jouini, A. (2006). Mater. Res. Bull. 41, 569-575.]). For halogen bonding, see: Metrangolo & Resnati (2001[Metrangolo, P. & Resnati, G. (2001). Chem. Eur. J. 7, 2511-2519.], 2008[Metrangolo, P. & Resnati, G. (2008). Science (Washington, DC), 321, 918-919.]); Politzer et al. (2007[Politzer, P., Lane, P., Concha, M. C., Ma, Y. & Murray, J. S. (2007). J. Mol. Model. 13, 305-311.]). For van der Waals radii, see: Bondi (1964[Bondi, A. (1964). J. Phys. Chem. 68, 441-451.]).

[Scheme 1]

Experimental

Crystal data
  • C6H9ClN22+·2H2PO4-

  • Mr = 338.57

  • Orthorhombic, P 21 21 21

  • a = 7.0084 (8) Å

  • b = 7.9404 (9) Å

  • c = 23.064 (3) Å

  • V = 1283.5 (3) Å3

  • Z = 4

  • Mo K[alpha] radiation

  • [mu] = 0.58 mm-1

  • T = 100 K

  • 0.55 × 0.52 × 0.51 mm

Data collection
  • Bruker SMART APEX CCD diffractometer

  • Absorption correction: multi-scan (SADABS; Bruker, 2011[Bruker (2011). APEX2, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.]) Tmin = 0.689, Tmax = 0.746

  • 11671 measured reflections

  • 4134 independent reflections

  • 4060 reflections with I > 2[sigma](I)

  • Rint = 0.021

Refinement
  • R[F2 > 2[sigma](F2)] = 0.025

  • wR(F2) = 0.064

  • S = 1.11

  • 4134 reflections

  • 186 parameters

  • H-atom parameters constrained

  • [Delta][rho]max = 0.44 e Å-3

  • [Delta][rho]min = -0.27 e Å-3

  • Absolute structure: Flack (1983[Flack, H. D. (1983). Acta Cryst. A39, 876-881.]), 1694 Friedel pairs

  • Flack parameter: 0.11 (4)

Table 1
Hydrogen-bond geometry (Å, °)

D-H...A D-H H...A D...A D-H...A
N1-H1A...O7i 0.91 1.76 2.6726 (15) 175
N1-H1B...O4ii 0.91 1.88 2.7807 (15) 172
N1-H1C...O2iii 0.91 2.05 2.9155 (15) 158
N2-H2A...O8 0.91 1.88 2.7886 (15) 178
N2-H2B...O7iv 0.91 1.84 2.7450 (15) 178
N2-H2C...O4 0.91 1.75 2.6545 (15) 175
O1-H1D...O2v 0.84 1.90 2.6525 (14) 148
O3-H3A...O8vi 0.84 1.79 2.5863 (14) 158
O5-H5...O8vii 0.84 2.00 2.6585 (14) 134
O6-H6A...O2 0.84 1.79 2.5841 (14) 156
O6B-H6B...O2 0.84 1.84 2.63 (3) 157
Symmetry codes: (i) [-x+3, y-{\script{1\over 2}}, -z+{\script{3\over 2}}]; (ii) [-x+2, y+{\script{1\over 2}}, -z+{\script{3\over 2}}]; (iii) [-x+3, y+{\script{1\over 2}}, -z+{\script{3\over 2}}]; (iv) x-1, y, z; (v) [x-{\script{1\over 2}}, -y-{\script{1\over 2}}, -z+1]; (vi) x, y-1, z; (vii) [x+{\script{1\over 2}}, -y+{\script{1\over 2}}, -z+1].

Data collection: APEX2 (Bruker, 2011[Bruker (2011). APEX2, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.]); cell refinement: SAINT (Bruker, 2011[Bruker (2011). APEX2, SAINT and SADABS. 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.]) and SHELXLE (Hübschle et al., 2011[Hübschle, C. B., Sheldrick, G. M. & Dittrich, B. (2011). J. Appl. Cryst. 44, 1281-1284.]); molecular graphics: SHELXTL (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); software used to prepare material for publication: SHELXTL and 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: RU2048 ).


Acknowledgements

The authors acknowledge the support provided by the Secretary of State for Scientific Research and Technology of Tunisia. The diffractometer was funded by NSF grant No. 0087210, by Ohio Board of Regents grant CAP-491 and by YSU.

References

Bondi, A. (1964). J. Phys. Chem. 68, 441-451.  [CrossRef] [ChemPort] [ISI]
Bruker (2011). APEX2, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.
Chtioui, A. & Jouini, A. (2006). Mater. Res. Bull. 41, 569-575.  [ISI] [CSD] [CrossRef] [ChemPort]
Flack, H. D. (1983). Acta Cryst. A39, 876-881.  [CrossRef] [details]
Hübschle, C. B., Sheldrick, G. M. & Dittrich, B. (2011). J. Appl. Cryst. 44, 1281-1284.  [ISI] [CrossRef] [details]
Kaabi, K., Ben Nasr, C. & Lefebvre, F. (2004). Mater. Res. Bull. 39, 205-215.  [ISI] [CSD] [CrossRef] [ChemPort]
Masse, R., Bagieu-Beucher, M., Pecaut, J., Levy, J. P. & Zyss, J. (1993). Nonlinear Opt. 5, 413-423.  [ChemPort]
Metrangolo, P. & Resnati, G. (2001). Chem. Eur. J. 7, 2511-2519.  [CrossRef] [PubMed] [ChemPort]
Metrangolo, P. & Resnati, G. (2008). Science (Washington, DC), 321, 918-919.
Oueslati, A., Ben Nasr, C., Durif, A. & Lefebvre, F. (2005). Mater. Res. Bull. 39, 970-980.  [ISI] [CrossRef]
Politzer, P., Lane, P., Concha, M. C., Ma, Y. & Murray, J. S. (2007). J. Mol. Model. 13, 305-311.  [ISI] [CrossRef] [PubMed] [ChemPort]
Rayes, A., Ben Nasr, C. & Rzaigui, M. (2004). Mater. Res. Bull. 39, 1113-1121.  [ISI] [CSD] [CrossRef] [ChemPort]
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.  [CrossRef] [details]
Westrip, S. P. (2010). J. Appl. Cryst. 43, 920-925.  [ISI] [CrossRef] [ChemPort] [details]


Acta Cryst (2013). E69, o159-o160   [ doi:10.1107/S1600536812051434 ]

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