Bis(adeninium) bis­(hydrogensulfate) sulfate

Guenifa, F.; Bendjeddou, L.; Cherouana, A.; Dahaoui, S.; Lecomte, C.

doi:10.1107/S1600536812044728

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 (C-C) = 0.003 Å
R = 0.043
wR = 0.131
Data-to-parameter ratio = 16.1
Details

Bis(adeninium) bis(hydrogensulfate) sulfate

Fatiha Guenifa,^a Lamia Bendjeddou,^a ^* Aouatef Cherouana,^a Slimane Dahaoui ^b and Claude Lecomte ^b

^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^-·SO₄^2-, 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-HO and O-HO hydrogen bonds, and weak C-HO and C-HN hydrogen bonds, generating a three-dimensional network.

Related literature

For background to the title compound, see: Biradha et al. (2010); Guenifa et al. (2009); Zeghouan et al. (2012). For related structures, see: Bendjeddou et al. (2003); Fun et al. (2011). For hydrogen-bond motifs, see: Bernstein et al. (1995).

Experimental

Crystal data

2C₅H₇N₅⁺·2HSO₄^-·SO₄^2-
M_r = 564.54
Monoclinic, C 2/c
a = 26.370 (5) Å
b = 8.970 (2) Å
c = 20.350 (4) Å
= 126.184 (10)°
V = 3885.2 (15) Å³
Z = 8
Mo K radiation
= 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(I)

Refinement

R[F² > 2(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
_max = 1.09 e Å^-3
_min = -0.60 e Å^-3

Table 1
Hydrogen-bond geometry (Å, °)

D-HA	D-H	HA	DA	D-HA
O5-H5O4ⁱ	0.84 (2)	1.74 (2)	2.580 (2)	174 (3)
O11-H11O1ⁱⁱ	0.91 (3)	1.56 (2)	2.457 (2)	166 (4)
N1A-H1AO2ⁱⁱ	0.912 (18)	1.92 (2)	2.760 (3)	151 (3)
N1B-H1BO7	0.880 (18)	2.28 (2)	3.027 (3)	142 (2)
N1B-H1BO10	0.880 (18)	2.18 (2)	2.870 (3)	136 (2)
N2A-H21AO3ⁱⁱⁱ	0.89 (2)	1.96 (2)	2.796 (3)	156 (2)
N2A-H22AO2ⁱⁱ	0.911 (18)	2.17 (2)	2.884 (3)	135 (2)
N2A-H22AO9ⁱⁱⁱ	0.911 (18)	2.22 (2)	2.814 (3)	122 (2)
N2B-H21BO10	0.885 (18)	2.01 (3)	2.760 (3)	142 (3)
N2B-H22BO12^iv	0.91 (2)	1.94 (2)	2.817 (3)	162 (2)
N7A-H7AO3ⁱⁱⁱ	0.888 (17)	1.96 (2)	2.757 (2)	149 (2)
N7B-H7BO1^v	0.916 (17)	2.28 (2)	2.858 (3)	121 (2)
N7B-H7BO12^iv	0.916 (17)	1.97 (2)	2.763 (3)	145 (2)
N9A-H9AO8^vi	0.89 (2)	1.95 (2)	2.767 (3)	152.3 (18)
N9B-H9BO7^vii	0.87 (2)	1.920 (19)	2.775 (3)	166 (2)
C2A-H2AO6^viii	0.93	2.21	2.913 (3)	131
C2A-H2AN3B^vi	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); cell refinement: DENZO and SCALEPACK (Otwinowski & Minor, 1997); data reduction: DENZO and SCALEPACK; program(s) used to solve structure: SIR2002 (Burla et al., 2003); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 (Farrugia, 1997); software used to prepare material for publication: WinGX (Farrugia, 1999), PARST97 (Nardelli, 1995), Mercury (Macrae et al., 2006) and POVRay (Persistence of Vision Team, 2004).

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

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Zeghouan, O., Bendjeddou, L., Cherouana, A., Dahaoui, S. & Lecomte, C. (2012). Acta Cryst. E68, o2959-o2960.

organic compounds