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

Mrad, M.L.; Zeller, M.; Rzaigui, M.; Ben Nasr, C.

doi:10.1107/S1600536812051434

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 (C-C) = 0.002 Å
Disorder in main residue
R = 0.025
wR = 0.064
Data-to-parameter ratio = 22.2
Details

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

Mohamed Lahbib Mrad,^a Matthias Zeller,^b Mohamed Rzaigui ^a and Cherif Ben Nasr ^a ^*

^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-HO hydrogen bonds to form two-dimensional infinite layers parallel to (001). The organic entities are anchored to the inorganic layers through N-HO hydrogen bonds, and through weak C-ClO 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). For network geometries, see: Rayes et al. (2004); Oueslati et al. (2005). For reference structural data, see: Kaabi et al. (2004); Chtioui & Jouini (2006). For halogen bonding, see: Metrangolo & Resnati (2001, 2008); Politzer et al. (2007). For van der Waals radii, see: Bondi (1964).

Experimental

Crystal data

C₆H₉ClN₂²⁺·2H₂PO₄^-
M_r = 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 radiation
= 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) T_min = 0.689, T_max = 0.746
11671 measured reflections
4134 independent reflections
4060 reflections with I > 2(I)
R_int = 0.021

Refinement

R[F² > 2(F²)] = 0.025
wR(F²) = 0.064
S = 1.11
4134 reflections
186 parameters
H-atom parameters constrained
_max = 0.44 e Å^-3
_min = -0.27 e Å^-3
Absolute structure: Flack (1983), 1694 Friedel pairs
Flack parameter: 0.11 (4)

Table 1
Hydrogen-bond geometry (Å, °)

D-HA	D-H	HA	DA	D-HA
N1-H1AO7ⁱ	0.91	1.76	2.6726 (15)	175
N1-H1BO4ⁱⁱ	0.91	1.88	2.7807 (15)	172
N1-H1CO2ⁱⁱⁱ	0.91	2.05	2.9155 (15)	158
N2-H2AO8	0.91	1.88	2.7886 (15)	178
N2-H2BO7^iv	0.91	1.84	2.7450 (15)	178
N2-H2CO4	0.91	1.75	2.6545 (15)	175
O1-H1DO2^v	0.84	1.90	2.6525 (14)	148
O3-H3AO8^vi	0.84	1.79	2.5863 (14)	158
O5-H5O8^vii	0.84	2.00	2.6585 (14)	134
O6-H6AO2	0.84	1.79	2.5841 (14)	156
O6B-H6BO2	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); cell refinement: SAINT (Bruker, 2011); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008) and SHELXLE (Hübschle et al., 2011); molecular graphics: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXTL and publCIF (Westrip, 2010).

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

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Bruker (2011). APEX2, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.
Chtioui, A. & Jouini, A. (2006). Mater. Res. Bull. 41, 569-575.
Flack, H. D. (1983). Acta Cryst. A39, 876-881.
Hübschle, C. B., Sheldrick, G. M. & Dittrich, B. (2011). J. Appl. Cryst. 44, 1281-1284.
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Masse, R., Bagieu-Beucher, M., Pecaut, J., Levy, J. P. & Zyss, J. (1993). Nonlinear Opt. 5, 413-423.
Metrangolo, P. & Resnati, G. (2001). Chem. Eur. J. 7, 2511-2519.
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.
Politzer, P., Lane, P., Concha, M. C., Ma, Y. & Murray, J. S. (2007). J. Mol. Model. 13, 305-311.
Rayes, A., Ben Nasr, C. & Rzaigui, M. (2004). Mater. Res. Bull. 39, 1113-1121.
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.
Westrip, S. P. (2010). J. Appl. Cryst. 43, 920-925.

organic compounds