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Volume 69 
Part 8 
Page o1278  
August 2013  

Received 18 May 2013
Accepted 9 July 2013
Online 20 July 2013

Key indicators
Single-crystal X-ray study
T = 293 K
Mean [sigma](C-C) = 0.002 Å
R = 0.042
wR = 0.123
Data-to-parameter ratio = 30.1
Details
Open access

1,4,8,11-Tetraazoniacyclotetradecane tetrakis(hydrogensulfate)

aLaboratoire Physico-chimie de l'État Solide, Département de Chimie, Faculté des Sciences de Sfax, Université de Sfax, BP 1171, 3000 Sfax, Tunisia, and bLaboratoire Sciences Chimiques de Rennes (CNRS, UMR 6226), Université de Rennes 1, Avenue du Général Leclerc, 35042 Rennes CEDEX, France
Correspondence e-mail: houcine_naili@yahoo.com

In the title salt, C10H28N44+·4HSO4-, the cation lies about an inversion center. In the crystal, O-H...O and N-H...O hydrogen bonds connect the anions and cations, forming a three-dimensional network.

Related literature

For the chemistry and applications of macrocyclic polyamine ligands, see: Wainwright (2001[Wainwright, K. P. (2001). Adv. Inorg. Chem. 52, 293-334.]); Lukes et al. (2001[Lukes, I., Kotek, J., Vojtisek, P. & Hermann, P. (2001). Coord. Chem. Rev. 216-217, 287-312.]); Zhang et al. (2003[Zhang, S., Merritt, M., Woessner, D. E., Lenkinski, R. E. & Sherry, A. D. (2003). Acc. Chem. Res. 36, 783-790.]); Liu (2004[Liu, S. (2004). Chem. Soc. Rev. 33, 445-461.]). For related structures, see: Melson (1979[Melson, G. A. (1979). Coordination Chemistry of Macrocyclic Compounds. New York: Plenum.]); Subramanian & Zaworotko (1995[Subramanian, S. & Zaworotko, M. J. (1995). Can. J. Chem. 73, 414-424.]); Ferchichi et al. (2010[Ferchichi, T., Trojett, B., Dhaouadi, H. & Marouani, H. (2010). Acta Cryst. E66, m869-m870.]); Pojarová et al. (2010[Pojarová, M., Fejfarová, K. & El Bali, B. (2010). Acta Cryst. E66, m1103.]).

[Scheme 1]

Experimental

Crystal data
  • C10H28N44+·4HSO4-

  • Mr = 592.68

  • Monoclinic, P 21 /c

  • a = 7.8177 (2) Å

  • b = 16.6464 (3) Å

  • c = 8.7222 (2) Å

  • [beta] = 97.165 (1)°

  • V = 1126.21 (4) Å3

  • Z = 2

  • Mo K[alpha] radiation

  • [mu] = 0.51 mm-1

  • T = 293 K

  • 0.03 × 0.02 × 0.01 mm

Data collection
  • Nonius KappaCCD diffractometer

  • Absorption correction: analytical (face-indexed; de Meulenaer & Tompa, 1965[Meulenaer, J. de & Tompa, H. (1965). Acta Cryst. 19, 1014-1018.]) Tmin = 0.988, Tmax = 0.995

  • 18757 measured reflections

  • 4952 independent reflections

  • 4074 reflections with I > 2[sigma](I)

  • Rint = 0.060

Refinement
  • R[F2 > 2[sigma](F2)] = 0.042

  • wR(F2) = 0.123

  • S = 1.05

  • 4952 reflections

  • 163 parameters

  • H-atom parameters constrained

  • [Delta][rho]max = 0.65 e Å-3

  • [Delta][rho]min = -0.54 e Å-3

Table 1
Hydrogen-bond geometry (Å, °)

D-H...A D-H H...A D...A D-H...A
N1-H1A...O4i 0.90 2.60 3.2773 (18) 133
N1-H1A...O1i 0.90 1.97 2.8445 (14) 165
N1-H1B...O4 0.90 1.91 2.8051 (16) 171
N2-H2A...O3ii 0.90 2.02 2.8675 (15) 156
N2-H2B...O3iii 0.90 2.09 2.9117 (14) 151
N2-H2A...O7iv 0.90 2.45 2.9232 (15) 113
O2-H1...O8i 0.73 1.89 2.6125 (18) 172
O6-H2...O1v 0.91 1.85 2.7544 (17) 172
Symmetry codes: (i) -x+1, -y+1, -z; (ii) -x, -y+1, -z; (iii) [-x, y-{\script{1\over 2}}, -z-{\script{1\over 2}}]; (iv) [x, -y+{\script{1\over 2}}, z-{\script{1\over 2}}]; (v) [-x+1, y-{\script{1\over 2}}, -z+{\script{1\over 2}}].

Data collection: COLLECT (Nonius, 1998[Nonius (1998). COLLECT. Nonius BV, Delft, The Netherlands.]); 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: 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: DIAMOND (Brandenburg & Berndt, 1999[Brandenburg, K. & Berndt, M. (1999). DIAMOND. Crystal Impact GbR, Bonn, Germany.]); software used to prepare material for publication: WinGX (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: LH5619 ).


Acknowledgements

Grateful thanks are expressed to Dr T. Roisnel (Centre de Diffractométrie X, Université de Rennes 1) for the X-ray data collection.

References

Brandenburg, K. & Berndt, M. (1999). DIAMOND. Crystal Impact GbR, Bonn, Germany.
Farrugia, L. J. (2012). J. Appl. Cryst. 45, 849-854.  [Web of Science] [CrossRef] [ChemPort] [IUCr Journals]
Ferchichi, T., Trojett, B., Dhaouadi, H. & Marouani, H. (2010). Acta Cryst. E66, m869-m870.  [CSD] [CrossRef] [ChemPort] [IUCr Journals]
Liu, S. (2004). Chem. Soc. Rev. 33, 445-461.  [Web of Science] [CrossRef] [PubMed] [ChemPort]
Lukes, I., Kotek, J., Vojtisek, P. & Hermann, P. (2001). Coord. Chem. Rev. 216-217, 287-312.  [Web of Science] [CrossRef] [ChemPort]
Melson, G. A. (1979). Coordination Chemistry of Macrocyclic Compounds. New York: Plenum.
Meulenaer, J. de & Tompa, H. (1965). Acta Cryst. 19, 1014-1018.  [CrossRef] [IUCr Journals]
Nonius (1998). COLLECT. Nonius BV, Delft, The Netherlands.
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.
Pojarová, M., Fejfarová, K. & El Bali, B. (2010). Acta Cryst. E66, m1103.  [CSD] [CrossRef] [IUCr Journals]
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.  [CrossRef] [ChemPort] [IUCr Journals]
Subramanian, S. & Zaworotko, M. J. (1995). Can. J. Chem. 73, 414-424.  [CrossRef] [ChemPort] [Web of Science]
Wainwright, K. P. (2001). Adv. Inorg. Chem. 52, 293-334.  [Web of Science] [CrossRef] [ChemPort]
Zhang, S., Merritt, M., Woessner, D. E., Lenkinski, R. E. & Sherry, A. D. (2003). Acc. Chem. Res. 36, 783-790.  [Web of Science] [CrossRef] [PubMed] [ChemPort]


Acta Cryst (2013). E69, o1278  [ doi:10.1107/S1600536813018953 ]

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