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Volume 69 
Part 4 
Page o600  
April 2013  

Received 4 March 2013
Accepted 18 March 2013
Online 28 March 2013

Key indicators
Single-crystal X-ray study
T = 100 K
Mean [sigma](C-C) = 0.002 Å
R = 0.024
wR = 0.053
Data-to-parameter ratio = 12.4
Details
Open access

o-Phenylenediaminium chloride nitrate

aLaboratoire de Chimie des Matériaux, Faculté des Sciences de Bizerte, 7021 Zarzouna, Tunisia, and bCristallographie, Résonance Magnétique et Modélisations (CRM2), UMR CNRS-UHP 7036, Institut Jean Barriol, Université de Lorraine, BP 70239, Boulevard des Aiguillettes, 54506 Vandoeuvre-les-Nancy, France
Correspondence e-mail: cherif_bennasr@yahoo.fr

In the title molecular salt, C6H10N22+·NO3-·Cl-, the complete cation is generated by a crystallographic mirror plane. The complete nitrate ion is also generated by reflection, with the N atom and one O atom lying on the mirror plane; the chloride ion also lies on the reflection plane. In the crystal, the components are linked by N-H...Cl and N-H...(N,O) hydrogen bonds, forming (001) layers with the benzene rings projecting into the interlayer regions. The layers are linked by weak C-H...O hydrogen bonds, generating a three-dimensional network.

Related literature

For background to inorganic-organic hybrid compounds, see: Bringley & Rajeswaram (2006[Bringley, J. F. & Rajeswaran, M. (2006). Acta Cryst. E62, m1304-m1305.]); Dai et al. (2002[Dai, J.-C., Wu, X.-T., Fu, Z.-Y., Cui, C.-P., Wu, S.-M., Du, W.-X., Wu, L.-M., Zhang, H.-H. & Sun, Q.-Q. (2002). Inorg. Chem. 41, 1391-1396.]). For reference structural data, see: Riahi et al. (2012[Riahi, S., Mrad, M. L., Jeanneau, E., Lefebvre, F. & Ben Nasr, C. (2012). Elixir Appl. Chem. 51, 10855-10860.]); Engh & Huber (1991[Engh, R. A. & Huber, R. (1991). Acta Cryst. A47, 392-400.]).

[Scheme 1]

Experimental

Crystal data
  • C6H10N22+·Cl-·NO3-

  • Mr = 207.61

  • Orthorhombic, P n m a

  • a = 7.3695 (5) Å

  • b = 8.2367 (5) Å

  • c = 14.2398 (7) Å

  • V = 864.36 (8) Å3

  • Z = 4

  • Ag K[alpha] radiation

  • [lambda] = 0.56085 Å

  • [mu] = 0.22 mm-1

  • T = 100 K

  • 0.27 × 0.20 × 0.15 mm

Data collection
  • Bruker Photon100 CMOS detector diffractometer

  • Absorption correction: multi-scan (SADABS; Bruker, 2004[Bruker (2004). COLLECT. Bruker AXS Inc., Madison, Wisconsin, USA.]) Tmin = 0.751, Tmax = 0.967

  • 26823 measured reflections

  • 812 independent reflections

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

  • Rint = 0.049

Refinement
  • R[F2 > 2[sigma](F2)] = 0.024

  • wR(F2) = 0.053

  • S = 0.80

  • 812 reflections

  • 66 parameters

  • 12 restraints

  • H atoms treated by a mixture of independent and constrained refinement

  • [Delta][rho]max = 0.27 e Å-3

  • [Delta][rho]min = -0.26 e Å-3

Table 1
Hydrogen-bond geometry (Å, °)

D-H...A D-H H...A D...A D-H...A
N3-H34...O10 1.033 (4) 2.41 (1) 2.896 (2) 107.4 (9)
N3-H34...N1 1.033 (4) 2.429 (9) 3.263 (2) 137.1 (8)
N3-H31...Cl1i 1.033 (4) 2.181 (4) 3.179 (2) 161.8 (5)
N3-H32...Cl1 1.033 (4) 2.183 (5) 3.156 (2) 156.2 (5)
C2-H2...O11 1.08 2.48 3.299 (2) 132
C1-H1...O10ii 1.08 2.52 3.427 (2) 141
Symmetry codes: (i) [x-{\script{1\over 2}}, -y+{\script{1\over 2}}, -z+{\script{1\over 2}}]; (ii) -x, -y+1, -z+1.

Data collection: COLLECT (Bruker, 2004[Bruker (2004). COLLECT. Bruker AXS Inc., Madison, Wisconsin, USA.]); cell refinement: SCALEPACK (Otwinowski & Minor, 1997[Otwinowski, Z. & Minor, W. (1997). Methods in Enzymology, Vol. 276, Macromolecular Crystallography, Part A, edited by C. W. Carter Jr & R. M. Sweet, pp. 307-326. New York: Academic Press.]); data reduction: DENZO (Otwinowski & Minor, 1997[Otwinowski, Z. & Minor, W. (1997). Methods in Enzymology, Vol. 276, Macromolecular Crystallography, Part A, edited by C. W. Carter Jr & R. M. Sweet, pp. 307-326. New York: Academic Press.]) and SCALEPACK; program(s) used to solve structure: SIR92 (Altomare et al., 1994[Altomare, A., Cascarano, G., Giacovazzo, C., Guagliardi, A., Burla, M. C., Polidori, G. & Camalli, M. (1994). J. Appl. Cryst. 27, 435.]); program(s) used to refine structure: MoPro (Jelsch et al., 2005[Jelsch, C., Guillot, B., Lagoutte, A. & Lecomte, C. (2005). J. Appl. Cryst. 38, 38-54.]); molecular graphics: DIAMOND (Brandenburg, 1998[Brandenburg, K. (1998). DIAMOND. University of Bonn, Germany.]); 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: HB7052 ).


Acknowledgements

We thank the Secretary of State for Scientific Research and Technology of Tunisia for financial support.

References

Altomare, A., Cascarano, G., Giacovazzo, C., Guagliardi, A., Burla, M. C., Polidori, G. & Camalli, M. (1994). J. Appl. Cryst. 27, 435.  [CrossRef] [details]
Brandenburg, K. (1998). DIAMOND. University of Bonn, Germany.
Bringley, J. F. & Rajeswaran, M. (2006). Acta Cryst. E62, m1304-m1305.  [CSD] [CrossRef] [details]
Bruker (2004). COLLECT. Bruker AXS Inc., Madison, Wisconsin, USA.
Dai, J.-C., Wu, X.-T., Fu, Z.-Y., Cui, C.-P., Wu, S.-M., Du, W.-X., Wu, L.-M., Zhang, H.-H. & Sun, Q.-Q. (2002). Inorg. Chem. 41, 1391-1396.  [ISI] [CSD] [CrossRef] [PubMed] [ChemPort]
Engh, R. A. & Huber, R. (1991). Acta Cryst. A47, 392-400.  [CrossRef] [details]
Jelsch, C., Guillot, B., Lagoutte, A. & Lecomte, C. (2005). J. Appl. Cryst. 38, 38-54.  [ISI] [CrossRef] [details]
Otwinowski, Z. & Minor, W. (1997). Methods in Enzymology, Vol. 276, Macromolecular Crystallography, Part A, edited by C. W. Carter Jr & R. M. Sweet, pp. 307-326. New York: Academic Press.
Riahi, S., Mrad, M. L., Jeanneau, E., Lefebvre, F. & Ben Nasr, C. (2012). Elixir Appl. Chem. 51, 10855-10860.
Westrip, S. P. (2010). J. Appl. Cryst. 43, 920-925.  [ISI] [CrossRef] [ChemPort] [details]


Acta Cryst (2013). E69, o600  [ doi:10.1107/S1600536813007447 ]

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