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Volume 68 
Part 12 
Pages o3266-o3267  
December 2012  

Received 16 October 2012
Accepted 29 October 2012
Online 3 November 2012

Key indicators
Single-crystal X-ray study
T = 120 K
Mean [sigma](C-C) = 0.003 Å
R = 0.043
wR = 0.131
Data-to-parameter ratio = 16.1
Details
Open access

Bis(adeninium) bis(hydrogensulfate) sulfate

aUnité de Recherche Chimie de l'Environnement et Moléculaire Structurale (CHEMS), Faculté des Sciences Exactes, Campus Chaabet Ersas, Université Mentouri de Constantine, 25000 Constantine, Algeria, and bCristallographie, Résonance Magnétique et Modélisation (CRM2), Université Henri Poincaré, Nancy 1, Faculté des Sciences, BP 70239, 54506 Vandoeuvre lès Nancy CEDEX, France
Correspondence e-mail: Lamiabendjeddou@yahoo.fr

The title compound, 2C5H7N52+·2HSO4-·SO42-, was synthesized from adenine and sulfuric acid. The asymmetric unit contains two diprotonated adeninium cations, two bisulfate anions and one sulfate anion. The crystal structure is stabilized by classical N-H...O and O-H...O hydrogen bonds, and weak C-H...O and C-H...N hydrogen bonds, generating a three-dimensional network.

Related literature

For background to the title compound, see: Biradha et al. (2010[Biradha, K., Samai, S., Maity, A. C. & Goswami, S. (2010). Cryst. Growth Des. 10, 937-942.]); Guenifa et al. (2009[Guenifa, F., Bendjeddou, L., Cherouana, A., Dahaoui, S. & Lecomte, C. (2009). Acta Cryst. E65, o2264-o2265.]); Zeghouan et al. (2012[Zeghouan, O., Bendjeddou, L., Cherouana, A., Dahaoui, S. & Lecomte, C. (2012). Acta Cryst. E68, o2959-o2960.]). For related structures, see: Bendjeddou et al. (2003[Bendjeddou, L., Cherouana, A., Dahaoui, S., Benali-Cherif, N. & Lecomte, C. (2003). Acta Cryst. E59, o649-o651.]); Fun et al. (2011[Fun, H.-K., Goh, J. H., Maity, A. C. & Goswami, S. (2011). Acta Cryst. E67, o427.]). For hydrogen-bond motifs, see: Bernstein et al. (1995[Bernstein, J., Davis, R. E., Shimoni, L. & Chang, N. (1995). Angew. Chem. Int. Ed. Engl. 34, 1555-1573.]).

[Scheme 1]

Experimental

Crystal data
  • 2C5H7N5+·2HSO4-·SO42-

  • Mr = 564.54

  • Monoclinic, C 2/c

  • a = 26.370 (5) Å

  • b = 8.970 (2) Å

  • c = 20.350 (4) Å

  • [beta] = 126.184 (10)°

  • V = 3885.2 (15) Å3

  • Z = 8

  • Mo K[alpha] radiation

  • [mu] = 0.48 mm-1

  • T = 120 K

  • 0.3 × 0.3 × 0.2 mm

Data collection
  • Nonius KappaCCD diffractometer

  • 5681 measured reflections

  • 5681 independent reflections

  • 3989 reflections with I > 2[sigma](I)

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

  • wR(F2) = 0.131

  • S = 1.07

  • 5681 reflections

  • 352 parameters

  • 12 restraints

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

  • [Delta][rho]max = 1.09 e Å-3

  • [Delta][rho]min = -0.60 e Å-3

Table 1
Hydrogen-bond geometry (Å, °)

D-H...A D-H H...A D...A D-H...A
O5-H5...O4i 0.84 (2) 1.74 (2) 2.580 (2) 174 (3)
O11-H11...O1ii 0.91 (3) 1.56 (2) 2.457 (2) 166 (4)
N1A-H1A...O2ii 0.912 (18) 1.92 (2) 2.760 (3) 151 (3)
N1B-H1B...O7 0.880 (18) 2.28 (2) 3.027 (3) 142 (2)
N1B-H1B...O10 0.880 (18) 2.18 (2) 2.870 (3) 136 (2)
N2A-H21A...O3iii 0.89 (2) 1.96 (2) 2.796 (3) 156 (2)
N2A-H22A...O2ii 0.911 (18) 2.17 (2) 2.884 (3) 135 (2)
N2A-H22A...O9iii 0.911 (18) 2.22 (2) 2.814 (3) 122 (2)
N2B-H21B...O10 0.885 (18) 2.01 (3) 2.760 (3) 142 (3)
N2B-H22B...O12iv 0.91 (2) 1.94 (2) 2.817 (3) 162 (2)
N7A-H7A...O3iii 0.888 (17) 1.96 (2) 2.757 (2) 149 (2)
N7B-H7B...O1v 0.916 (17) 2.28 (2) 2.858 (3) 121 (2)
N7B-H7B...O12iv 0.916 (17) 1.97 (2) 2.763 (3) 145 (2)
N9A-H9A...O8vi 0.89 (2) 1.95 (2) 2.767 (3) 152.3 (18)
N9B-H9B...O7vii 0.87 (2) 1.920 (19) 2.775 (3) 166 (2)
C2A-H2A...O6viii 0.93 2.21 2.913 (3) 131
C2A-H2A...N3Bvi 0.93 2.49 3.189 (3) 132
Symmetry codes: (i) [x, -y+1, z+{\script{1\over 2}}]; (ii) x, y-1, z; (iii) [-x+{\script{1\over 2}}, y-{\script{1\over 2}}, -z+{\script{1\over 2}}]; (iv) -x, -y+1, -z; (v) -x, -y+2, -z; (vi) [x, -y+1, z-{\script{1\over 2}}]; (vii) x, y+1, z; (viii) [x, -y, z-{\script{1\over 2}}].

Data collection: KappaCCD Reference Manual (Nonius, 1998[Nonius (1998). KappaCCD Reference Manual. Nonius BV, Delft, The Netherlands.]); cell refinement: DENZO and 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 and SCALEPACK; program(s) used to solve structure: SIR2002 (Burla et al., 2003[Burla, M. C., Camalli, M., Carrozzini, B., Cascarano, G. L., Giacovazzo, C., Polidori, G. & Spagna, R. (2003). J. Appl. Cryst. 36, 1103.]); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); molecular graphics: ORTEP-3 (Farrugia, 1997[Farrugia, L. J. (1997). J. Appl. Cryst. 30, 565.]); software used to prepare material for publication: WinGX (Farrugia, 1999[Farrugia, L. J. (1999). J. Appl. Cryst. 32, 837-838.]), PARST97 (Nardelli, 1995[Nardelli, M. (1995). J. Appl. Cryst. 28, 659.]), Mercury (Macrae et al., 2006[Macrae, C. F., Edgington, P. R., McCabe, P., Pidcock, E., Shields, G. P., Taylor, R., Towler, M. & van de Streek, J. (2006). J. Appl. Cryst. 39, 453-457.]) and POVRay (Persistence of Vision Team, 2004[Persistence of Vision Team (2004). POV-RAY. Persistence of Vision Raytracer Pty Ltd, Victoria, Australia. URL: http://www.povray.org/ .]).


Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: XU5635 ).


Acknowledgements

Technical support (X-ray measurements at SCDRX) from Université Henry Poincaré, Nancy 1, is gratefully acknowledged.

References

Bendjeddou, L., Cherouana, A., Dahaoui, S., Benali-Cherif, N. & Lecomte, C. (2003). Acta Cryst. E59, o649-o651.  [CSD] [CrossRef] [details]
Bernstein, J., Davis, R. E., Shimoni, L. & Chang, N. (1995). Angew. Chem. Int. Ed. Engl. 34, 1555-1573.  [CrossRef] [ChemPort] [ISI]
Biradha, K., Samai, S., Maity, A. C. & Goswami, S. (2010). Cryst. Growth Des. 10, 937-942.  [CrossRef] [ChemPort]
Burla, M. C., Camalli, M., Carrozzini, B., Cascarano, G. L., Giacovazzo, C., Polidori, G. & Spagna, R. (2003). J. Appl. Cryst. 36, 1103.  [CrossRef] [details]
Farrugia, L. J. (1997). J. Appl. Cryst. 30, 565.  [CrossRef] [details]
Farrugia, L. J. (1999). J. Appl. Cryst. 32, 837-838.  [CrossRef] [ChemPort] [details]
Fun, H.-K., Goh, J. H., Maity, A. C. & Goswami, S. (2011). Acta Cryst. E67, o427.  [CSD] [CrossRef] [details]
Guenifa, F., Bendjeddou, L., Cherouana, A., Dahaoui, S. & Lecomte, C. (2009). Acta Cryst. E65, o2264-o2265.  [CSD] [CrossRef] [details]
Macrae, C. F., Edgington, P. R., McCabe, P., Pidcock, E., Shields, G. P., Taylor, R., Towler, M. & van de Streek, J. (2006). J. Appl. Cryst. 39, 453-457.  [ISI] [CrossRef] [ChemPort] [details]
Nardelli, M. (1995). J. Appl. Cryst. 28, 659.  [CrossRef] [details]
Nonius (1998). KappaCCD Reference Manual. 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.
Persistence of Vision Team (2004). POV-RAY. Persistence of Vision Raytracer Pty Ltd, Victoria, Australia. URL: http://www.povray.org/ .
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.  [CrossRef] [details]
Zeghouan, O., Bendjeddou, L., Cherouana, A., Dahaoui, S. & Lecomte, C. (2012). Acta Cryst. E68, o2959-o2960.  [CSD] [CrossRef] [details]


Acta Cryst (2012). E68, o3266-o3267   [ doi:10.1107/S1600536812044728 ]

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