Quinolinium 8-hy­droxy-7-iodo­quinoline-5-sulfonate 0.8-hydrate

Smith, G.

doi:10.1107/S1600536812046247

Volume 68
Part 12
Page o3349
December 2012

Received 30 October 2012
Accepted 8 November 2012
Online 14 November 2012

Key indicators
Single-crystal X-ray study
T = 200 K
Mean (C-C) = 0.009 Å
Disorder in main residue
R = 0.040
wR = 0.082
Data-to-parameter ratio = 13.1
Details

Quinolinium 8-hydroxy-7-iodoquinoline-5-sulfonate 0.8-hydrate

Graham Smith ^a ^*

^aScience and Engineering Faculty, Queensland University of Technology, GPO Box 2434, Brisbane, 4001, Australia
Correspondence e-mail: g.smith@qut.edu.au

In the crystal structure of the title hydrated quinolinium salt of ferron (8-hydroxy-7-iodoquinoline-5-sulfonic acid), C₉H₇N⁺·C₉H₅INO₄S^-·0.8H₂O, the quinolinium cation is fully disordered over two sites (occupancy factors fixed at 0.63 and 0.37) lying essentially within a common plane and with the ferron anions forming [pi] - [pi] -associated stacks down the b axis [minimum ring centroid separation = 3.462 (6) Å]. The cations and anions are linked into chains extending along c through hydroxy O-HO and quinolinium N-HO hydrogen bonds to sulfonate O-atom acceptors which are also involved in water O-HO hydrogen-bonding interactions along b, giving a two-dimensional network.

Related literature

For the crystal structure of ferron, see: Balasubramanian & Muthiah (1996). For analytical applications of ferron, see: Vogel (1964). For the crystal structures of other non-zwitterionic compounds of ferron, see: Hemamalini et al. (2004); Smith et al. (2004, 2007).

Experimental

Crystal data

C₉H₈N⁺·C₉H₅INO₄S^-·0.8H₂O
M_r = 494.69
Orthorhombic, P c a 2₁
a = 16.2403 (5) Å
b = 7.1539 (3) Å
c = 15.2458 (5) Å
V = 1771.28 (11) Å³
Z = 4
Mo K radiation
= 1.96 mm^-1
T = 200 K
0.32 × 0.25 × 0.12 mm

Data collection

Oxford Diffraction Gemini-S CCD-detector diffractometer
Absorption correction: multi-scan (CrysAlis PRO; Agilent, 2012) T_min = 0.906, T_max = 0.980
6143 measured reflections
3207 independent reflections
2709 reflections with I > 2(I)
R_int = 0.028

Refinement

R[F² > 2(F²)] = 0.040
wR(F²) = 0.082
S = 1.18
3207 reflections
244 parameters
1 restraint
H-atom parameters constrained
_max = 0.65 e Å^-3
_min = -0.66 e Å^-3
Absolute structure: Flack (1983), 789 Friedel pairs
Flack parameter: 0.01 (3)

Table 1
Hydrogen-bond geometry (Å, °)

D-HA	D-H	HA	DA	D-HA
N1A-H1AO53ⁱ	0.86	1.97	2.783 (10)	157
N1B-H1BO53ⁱ	0.86	1.88	2.725 (16)	166
O8-H8O52ⁱⁱ	0.81	2.13	2.769 (7)	135
O1W-H11WO52	0.89	2.18	3.066 (9)	179
O1W-H12WO51ⁱⁱⁱ	0.90	2.18	3.080 (8)	178
Symmetry codes: (i) $[-x+1, -y+1, z+{\script{1\over 2}}]$ ; (ii) $[-x+1, -y+2, z+{\script{1\over 2}}]$ ; (iii) x, y+1, z.

Data collection: CrysAlis PRO (Agilent, 2012); cell refinement: CrysAlis PRO; data reduction: CrysAlis PRO; program(s) used to solve structure: SIR92 (Altomare et al., 1993); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008) within WinGX (Farrugia, 2012); molecular graphics: PLATON (Spek, 2009); software used to prepare material for publication: PLATON.

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: SU2523 ).

Acknowledgements

The author acknowledges financial support from the Science and Engineering Faculty and the University Library, Queensland University of Technology.

References

Agilent (2012). CrysAlis PRO. Agilent Technologies, Yarnton, England.
Altomare, A., Cascarano, G., Giacovazzo, C. & Guagliardi, A. (1993). J. Appl. Cryst. 26, 343-350.
Balasubramanian, T. & Muthiah, P. T. (1996). Acta Cryst. C52, 2072-2073.
Farrugia, L. J. (2012). J. Appl. Cryst. 45, 849-854.
Flack, H. D. (1983). Acta Cryst. A39, 876-881.
Hemamalini, M., Muthiah, P. T., Bocelli, G. & Cantoni, A. (2004). Acta Cryst. C60, o284-o286.
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.
Smith, G., Wermuth, U. D. & Healy, P. C. (2004). Acta Cryst. C60, o600-o603.
Smith, G., Wermuth, U. D. & Healy, P. C. (2007). Acta Cryst. C63, o405-o407.
Spek, A. L. (2009). Acta Cryst. D65, 148-155.
Vogel, A. I. (1964). Textbook of Macro and Semi-Micro Qualitative Inorganic Analysis, 4th ed., p. 266. London: Longmans.

organic compounds