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Volume 69 
Part 9 
Pages o1458-o1459  
September 2013  

Received 7 August 2013
Accepted 8 August 2013
Online 21 August 2013

Key indicators
Single-crystal X-ray study
T = 180 K
Mean [sigma](C-C) = 0.002 Å
R = 0.030
wR = 0.079
Data-to-parameter ratio = 13.3
Details
Open access

8-Hydroxyquinolin-1-ium hydrogen sulfate monohydrate

aUnité de Recherche de Chimie de l'Environnement et Moléculaire Structurale, CHEMS, Université Constantine 1, 25000, Algeria,bLaboratory of Solid State Chemistry and Mössbauer Spectroscopy, Laboratories for Inorganic Materials, Department of Chemistry and Biochemistry, Concordia University, Montreal, Quebec, H3G 1M8, Canada,cDépartement Sciences de la Matière, Faculté des Sciences Exactes et Sciences de la Nature et de la Vie, Université Oum El Bouaghi 04000, Algeria, and dLaboratoire de Chimie de Coordination, UPR CNRS 8241, 205 route de Narbonne, 31077 Toulouse Cedex, France
Correspondence e-mail: bouacida_sofiane@yahoo.fr

In the crystal structure of the title salt hydrate, C9H8NO+·HSO4-·H2O, the quinoline N-H atoms are hydrogen bonded to the bisulfate anions. The bisulfate anions and water molecules are linked together by O-H...O hydrogen-bonding interactions. The cations and anions form separate layers alternating along the c axis, which are linked by N-H...O and O-H...O hydrogen bonds into a two-dimensional network parallel to (100). Further O-H...O contacts connect these layers, forming a three-dimensional network, in which two R44(12) rings and C22(13) infinite chains can be identified.

Related literature

For background to and the biological activity of quinoline derivatives, see: Sasaki et al. (1998[Sasaki, K., Tsurumori, A. & Hirota, T. (1998). J. Chem. Soc. Perkin Trans. 1, pp. 3851-3856.]); Reux et al. (2009[Reux, B., Nevalainen, T., Raitio, K. H. & Koskinen, A. M. P. (2009). Bioorg. Med. Chem. 17, 4441-4447.]); Morimoto et al. (1991[Morimoto, Y., Matsuda, F. & Shirahama, H. (1991). Synlett, 3, 202-203.]); Markees et al. (1970[Markees, D. G., Dewey, V. C. & Kidder, G. W. (1970). J. Med. Chem. 13, 324-326.]). For related structures, see: Loh et al. (2010a[Loh, W.-S., Quah, C. K., Hemamalini, M. & Fun, H.-K. (2010a). Acta Cryst. E66, o2357.],b[Loh, W.-S., Quah, C. K., Hemamalini, M. & Fun, H.-K. (2010b). Acta Cryst. E66, o2396.]). For a description of the Cambridge Structural Database, see: Allen, (2002[Allen, F. H. (2002). Acta Cryst. B58, 380-388.]).

[Scheme 1]

Experimental

Crystal data
  • C9H8NO+·HSO4-·H2O

  • Mr = 261.25

  • Triclinic, [P \overline 1]

  • a = 6.5536 (4) Å

  • b = 8.0600 (5) Å

  • c = 11.3369 (6) Å

  • [alpha] = 100.068 (5)°

  • [beta] = 106.344 (4)°

  • [gamma] = 105.712 (5)°

  • V = 532.35 (5) Å3

  • Z = 2

  • Mo K[alpha] radiation

  • [mu] = 0.32 mm-1

  • T = 180 K

  • 0.43 × 0.16 × 0.08 mm

Data collection
  • Agilent Xcalibur (Sapphire1) diffractometer

  • Absorption correction: multi-scan (CrysAlis PRO; Agilent, 2011[Agilent, (2011). CrysAlis PRO. Agilent Technologies Ltd, Yarnton, England.]) Tmin = 0.874, Tmax = 0.975

  • 10891 measured reflections

  • 2171 independent reflections

  • 2000 reflections with I > 2[sigma](I)

  • Rint = 0.027

Refinement
  • R[F2 > 2[sigma](F2)] = 0.030

  • wR(F2) = 0.079

  • S = 1.05

  • 2171 reflections

  • 163 parameters

  • 3 restraints

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

  • [Delta][rho]max = 0.41 e Å-3

  • [Delta][rho]min = -0.39 e Å-3

Table 1
Hydrogen-bond geometry (Å, °)

D-H...A D-H H...A D...A D-H...A
N1-H1...O14 0.88 2.00 2.7690 (18) 145
O1W-H1W...O11i 0.85 (1) 1.89 (1) 2.7369 (17) 178 (1)
O1W-H2W...O14ii 0.85 (1) 2.03 (1) 2.8818 (19) 175 (1)
O9-H9...O13iii 0.84 1.81 2.6470 (16) 174
O12-H12...O1W 0.84 1.72 2.5529 (17) 172
Symmetry codes: (i) -x+1, -y+1, -z; (ii) x+1, y, z; (iii) -x+1, -y+1, -z+1.

Data collection: CrysAlis PRO (Agilent, 2011[Agilent, (2011). CrysAlis PRO. Agilent Technologies Ltd, Yarnton, England.]); cell refinement: CrysAlis PRO; data reduction: CrysAlis PRO; 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 for Windows (Farrugia, 2012[Farrugia, L. J. (2012). J. Appl. Cryst. 45, 849-854.]) and DIAMOND (Brandenburg & Berndt, 2001[Brandenburg, K. & Berndt, M. (2001). 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: HG5339 ).


Acknowledgements

This work was supported by the Unité de Recherche de Chimie de l'Environnement et Moléculaire Structurale, CHEMS, Université Constantine 1, Algeria and Laboratoire de Chimie de Coordination Toulouse, France. Thanks are due to the Ministére de l'Enseignement Supérieur et de la Recherche Scientifique - Algérie (via the PNR project) for financial support.

References

Agilent, (2011). CrysAlis PRO. Agilent Technologies Ltd, Yarnton, England.
Allen, F. H. (2002). Acta Cryst. B58, 380-388.  [ISI] [CrossRef] [details]
Brandenburg, K. & Berndt, M. (2001). DIAMOND. Crystal Impact GbR, Bonn, Germany.
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. (2012). J. Appl. Cryst. 45, 849-854.  [ISI] [CrossRef] [ChemPort] [details]
Loh, W.-S., Quah, C. K., Hemamalini, M. & Fun, H.-K. (2010a). Acta Cryst. E66, o2357.  [CSD] [CrossRef] [details]
Loh, W.-S., Quah, C. K., Hemamalini, M. & Fun, H.-K. (2010b). Acta Cryst. E66, o2396.  [CSD] [CrossRef] [details]
Markees, D. G., Dewey, V. C. & Kidder, G. W. (1970). J. Med. Chem. 13, 324-326.  [CrossRef] [ChemPort] [PubMed] [ISI]
Morimoto, Y., Matsuda, F. & Shirahama, H. (1991). Synlett, 3, 202-203.  [CrossRef]
Reux, B., Nevalainen, T., Raitio, K. H. & Koskinen, A. M. P. (2009). Bioorg. Med. Chem. 17, 4441-4447.  [CrossRef] [PubMed] [ChemPort]
Sasaki, K., Tsurumori, A. & Hirota, T. (1998). J. Chem. Soc. Perkin Trans. 1, pp. 3851-3856.  [CrossRef]
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.  [CrossRef] [ChemPort] [details]


Acta Cryst (2013). E69, o1458-o1459   [ doi:10.1107/S1600536813022319 ]

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