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ISSN: 2056-9890

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

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

(Received 30 October 2012; accepted 8 November 2012; online 14 November 2012)

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 ππ-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—H⋯O and quinolinium N—H⋯O hydrogen bonds to sulfonate O-atom acceptors which are also involved in water O—H⋯O hydrogen-bonding inter­actions along b, giving a two-dimensional network.

Related literature

For the crystal structure of ferron, see: Balasubramanian & Muthiah (1996[Balasubramanian, T. & Muthiah, P. T. (1996). Acta Cryst. C52, 2072-2073.]). For analytical applications of ferron, see: Vogel (1964[Vogel, A. I. (1964). Textbook of Macro and Semi-Micro Qualitative Inorganic Analysis, 4th ed., p. 266. London: Longmans.]). For the crystal structures of other non-zwitterionic compounds of ferron, see: Hemamalini et al. (2004[Hemamalini, M., Mu­thiah, P. T., Bocelli, G. & Cantoni, A. (2004). Acta Cryst. C60, o284-o286.]); Smith et al. (2004[Smith, G., Wermuth, U. D. & Healy, P. C. (2004). Acta Cryst. C60, o600-o603.], 2007[Smith, G., Wermuth, U. D. & Healy, P. C. (2007). Acta Cryst. C63, o405-o407.]).

[Scheme 1]

Experimental

Crystal data
  • C9H8N+·C9H5INO4S·0.8H2O

  • Mr = 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 Kα radiation

  • μ = 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[Agilent (2012). CrysAlis PRO. Agilent Technologies, Yarnton, England.]) Tmin = 0.906, Tmax = 0.980

  • 6143 measured reflections

  • 3207 independent reflections

  • 2709 reflections with I > 2σ(I)

  • Rint = 0.028

Refinement
  • R[F2 > 2σ(F2)] = 0.040

  • wR(F2) = 0.082

  • S = 1.18

  • 3207 reflections

  • 244 parameters

  • 1 restraint

  • H-atom parameters constrained

  • Δρmax = 0.65 e Å−3

  • Δρmin = −0.66 e Å−3

  • Absolute structure: Flack (1983[Flack, H. D. (1983). Acta Cryst. A39, 876-881.]), 789 Friedel pairs

  • Flack parameter: 0.01 (3)

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A D—H H⋯A DA D—H⋯A
N1A—H1A⋯O53i 0.86 1.97 2.783 (10) 157
N1B—H1B⋯O53i 0.86 1.88 2.725 (16) 166
O8—H8⋯O52ii 0.81 2.13 2.769 (7) 135
O1W—H11W⋯O52 0.89 2.18 3.066 (9) 179
O1W—H12W⋯O51iii 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[Agilent (2012). CrysAlis PRO. Agilent Technologies, Yarnton, England.]); cell refinement: CrysAlis PRO; data reduction: CrysAlis PRO; program(s) used to solve structure: SIR92 (Altomare et al., 1993[Altomare, A., Cascarano, G., Giacovazzo, C. & Guagliardi, A. (1993). J. Appl. Cryst. 26, 343-350.]); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]) within WinGX (Farrugia, 2012[Farrugia, L. J. (2012). J. Appl. Cryst. 45, 849-854.]); molecular graphics: PLATON (Spek, 2009[Spek, A. L. (2009). Acta Cryst. D65, 148-155.]); software used to prepare material for publication: PLATON.

Supporting information


Comment top

Ferron (8-hydroxy-7-iodoquinoline-5-sulfonic acid) is a bidentate complexing agent which has analytical applications as a selective colour reagent for the detection of iron(III) but not iron(II) (Vogel, 1964). The crystal structure of ferron (Balasubramanian & Muthiah, 1996) has shown that the molecule exists as a sulfonate-quinolinium zwitterion. As a sulfonic acid, ferron is potentially capable of protonating most Lewis bases, but the crystal structures of only a small number of such salts have been reported. With 8-hydroxyquinoline, a 1:1 sesquihydrate is formed (Smith et al., 2004) and with bifunctional 4,4'-bipyridine (Hemamalini et al., 2004) a monoprotonated 1:1 dihydrate is found. A common structural feature in these ferron proton-transfer salts is the presence of R22(10) cyclic hydrogen-bonded ferron···ferron dimers involving the 8-hydroxy donor and hetero-N acceptor groups. Reaction of ferron with quinoline gave the title chemically stable 1:1 hydrated salt, whose crystal structure is reported on herein.

In the title compound, Fig. 1, the quinolinium cation is fully disordered over two sites A and B with occupancy factors fixed at 0.63 and 0.37, lying essentially within a common plane. These cations are linked to the anions through both quinolinium N—H···O and hydroxyl O—H···O and hydrogen bonds to sulfonate O-atom acceptors (Table 1), forming chains extending along c. Water O—H···Osulfonate hydrogen-bonding interactions together with cation–anion ring ππ associations [minimum ring centroid separation = 3.462 (6) Å] link the chains down the b axial direction, giving a two-dimensional network structure (Figs. 2 and 3). The ferron–ferron dimeric association is not present. In the crystal, there are relatively short intra-anionic I7···O51iv interactions [3.027 (5) Å] [symmetry code (iv): x + 1/2,-y, z].

With the ferron anion, the short intra-anionic O8—H8···N1 association [2.693 (7) Å] is present, similar to that found in other non-zwitterionic compounds of ferron (Hemamalini et al., 2004; Smith et al., 2004, 2007). Also the common aromatic ring C6–H6···O51sulfonate association [2.827 (8) Å] maintains the S5–O51 bond close to the extended plane of the aromatic ring [torsion angle C10—C5—S5—O51, 171.1 (5) °].

Related literature top

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 top

The title compound was synthesized by heating a solution containing 1 mmol of 8-hydroxy-7-iodoquinoline-5-sulfonic acid (ferron) and 1 mmol of quinoline in 50 ml of 50% ethanol-water for 10 min under reflux. After concentration to ca. 40 ml, partial room temperature evaporation of the hot-filtered solution gave yellow flat prisms of the title compound (m.p. 460.6–462.3 K) from which a specimen was cleaved for the X-ray analysis.

Refinement top

Hydrogen atoms on the water molecule and the hydroxyl group were located in a difference-Fourier synthesis but were subsequently allowed to ride in the refinement with Uiso(H) = 1.5Ueq(O). Other H-atoms were included in the refinement in calculated positions with N—H = 0.86 Å or C—H = 0.93 Å and were also treated as riding, with Uiso(H) = 1.2Ueq(C). The site occupancy of the water molecule was determined as 0.801 (12) and was subsequently fixed as 0.80. The quinolinium cation was completely disordered laterally within a common plane and the minor component (B) was subsequently located and its occupancy determined as 0.373 (14). Because of the instability in the anisotropic displacement parameters for both components, these were refined isotropically. The maximum difference peak was 0.64 e Å-3 1.07 Å from I7.

Computing details top

Data collection: CrysAlis PRO (Agilent, 2012); cell refinement: CrysAlis PRO (Agilent, 2012); data reduction: CrysAlis PRO (Agilent, 2012); 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 (Spek, 2009).

Figures top
[Figure 1] Fig. 1. Molecular configuration and atom naming for the individual cation, the disordered anion components (A and B) and the water species in the title compound. The minor-occupancy B anion is shown with broken bonds and displacement ellipsoids are drawn at the 30% probability level. The intra- and inter-species hydrogen bonds are shown as a dashed lines.
[Figure 2] Fig. 2. The stacking of the cation and anion rings down the b axis in the crystal of the title compound.
[Figure 3] Fig. 3. A perspective view of the crystal packing of the title compound viewed along the a axis, showing the inter-chain water hydrogen-bonding associations (dashed lines; see Table for details; symmetry codes: (i) -x+1, -y+1, z+1/2; (ii) -x+1, -y+2, z+1/2; (iii) x, y+1, z).
Quinolinium 8-hydroxy-7-iodoquinoline-5-sulfonate 0.8-hydrate top
Crystal data top
C9H8N+·C9H5INO4S·0.8H2OF(000) = 976
Mr = 494.69Dx = 1.855 Mg m3
Orthorhombic, Pca21Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2c -2acCell parameters from 1806 reflections
a = 16.2403 (5) Åθ = 3.4–28.9°
b = 7.1539 (3) ŵ = 1.96 mm1
c = 15.2458 (5) ÅT = 200 K
V = 1771.28 (11) Å3Flat prism, yellow
Z = 40.32 × 0.25 × 0.12 mm
Data collection top
Oxford Diffraction Gemini-S CCD-detector
diffractometer
3207 independent reflections
Radiation source: fine-focus sealed tube2709 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.028
Detector resolution: 16.077 pixels mm-1θmax = 28.9°, θmin = 3.4°
ω scansh = 2215
Absorption correction: multi-scan
(CrysAlis PRO; Agilent, 2012)
k = 69
Tmin = 0.906, Tmax = 0.980l = 1919
6143 measured reflections
Refinement top
Refinement on F2Secondary atom site location: difference Fourier map
Least-squares matrix: fullHydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.040H-atom parameters constrained
wR(F2) = 0.082 w = 1/[σ2(Fo2) + (0.0181P)2 + 3.2291P]
where P = (Fo2 + 2Fc2)/3
S = 1.18(Δ/σ)max = 0.004
3207 reflectionsΔρmax = 0.65 e Å3
244 parametersΔρmin = 0.66 e Å3
1 restraintAbsolute structure: Flack (1983), 789 Friedel pairs
Primary atom site location: structure-invariant direct methodsAbsolute structure parameter: 0.01 (3)
Crystal data top
C9H8N+·C9H5INO4S·0.8H2OV = 1771.28 (11) Å3
Mr = 494.69Z = 4
Orthorhombic, Pca21Mo Kα radiation
a = 16.2403 (5) ŵ = 1.96 mm1
b = 7.1539 (3) ÅT = 200 K
c = 15.2458 (5) Å0.32 × 0.25 × 0.12 mm
Data collection top
Oxford Diffraction Gemini-S CCD-detector
diffractometer
3207 independent reflections
Absorption correction: multi-scan
(CrysAlis PRO; Agilent, 2012)
2709 reflections with I > 2σ(I)
Tmin = 0.906, Tmax = 0.980Rint = 0.028
6143 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.040H-atom parameters constrained
wR(F2) = 0.082Δρmax = 0.65 e Å3
S = 1.18Δρmin = 0.66 e Å3
3207 reflectionsAbsolute structure: Flack (1983), 789 Friedel pairs
244 parametersAbsolute structure parameter: 0.01 (3)
1 restraint
Special details top

Geometry. Bond distances, angles etc. have been calculated using the rounded fractional coordinates. All su's are estimated from the variances of the (full) variance-covariance matrix. The cell e.s.d.'s are taken into account in the estimation of distances, angles and torsion angles

Refinement. Refinement of F2 against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F2, conventional R-factors R are based on F, with F set to zero for negative F2. The threshold expression of F2 > σ(F2) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F2 are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/UeqOcc. (<1)
N1A0.5706 (6)0.4412 (12)0.3693 (6)0.020 (2)*0.630
C2A0.6389 (9)0.4939 (16)0.3279 (9)0.025 (3)*0.630
C3A0.6447 (7)0.4807 (15)0.2359 (9)0.019 (2)*0.630
C4A0.5784 (8)0.4161 (17)0.1888 (8)0.026 (3)*0.630
C5A0.4375 (7)0.2937 (15)0.1920 (9)0.023 (3)*0.630
C6A0.3681 (8)0.2443 (17)0.2377 (9)0.030 (2)*0.630
C7A0.3664 (8)0.2600 (17)0.3288 (10)0.026 (2)*0.630
C8A0.4325 (10)0.3261 (17)0.3750 (8)0.026 (3)*0.630
C9A0.5015 (8)0.3760 (17)0.3272 (8)0.021 (3)*0.630
C10A0.5084 (11)0.356 (3)0.2307 (12)0.022 (5)*0.630
C8B0.6037 (15)0.466 (3)0.3434 (14)0.020 (4)*0.370
C9B0.5273 (13)0.388 (3)0.3220 (12)0.013 (4)*0.370
C10B0.4986 (15)0.362 (3)0.2426 (16)0.006 (6)*0.370
C3B0.3682 (13)0.254 (3)0.2889 (17)0.029 (4)*0.370
C4B0.4180 (12)0.288 (3)0.2210 (14)0.020 (4)*0.370
C5B0.5542 (14)0.390 (3)0.1688 (15)0.032 (5)*0.370
C6B0.6308 (13)0.451 (3)0.1885 (15)0.030 (4)*0.370
C7B0.6552 (12)0.496 (3)0.2747 (15)0.022 (4)*0.370
N1B0.4736 (11)0.341 (2)0.3879 (10)0.022 (3)*0.370
C2B0.4005 (15)0.285 (3)0.3719 (14)0.028 (5)*0.370
I70.30996 (2)0.75195 (7)0.45473 (4)0.0259 (1)
S50.38785 (10)0.7547 (3)0.09027 (10)0.0232 (4)
O80.4943 (2)0.8886 (6)0.4574 (4)0.0265 (11)
O510.3101 (3)0.6580 (7)0.0999 (3)0.0327 (16)
O520.3807 (3)0.9388 (7)0.0506 (3)0.0280 (16)
O530.4497 (3)0.6391 (7)0.0466 (3)0.0323 (16)
N10.6037 (3)0.9565 (7)0.3285 (4)0.0220 (17)
C20.6580 (4)0.9911 (9)0.2656 (5)0.027 (2)
C30.6418 (4)0.9684 (9)0.1760 (5)0.0233 (19)
C40.5659 (4)0.9043 (9)0.1505 (4)0.0223 (19)
C50.4255 (4)0.7936 (7)0.1981 (4)0.0150 (17)
C60.3719 (4)0.7600 (9)0.2665 (4)0.0183 (17)
C70.3948 (4)0.7926 (7)0.3545 (4)0.0147 (17)
C80.4722 (4)0.8578 (8)0.3737 (4)0.0173 (17)
C90.5289 (4)0.8920 (8)0.3042 (4)0.0157 (17)
C100.5063 (4)0.8627 (8)0.2143 (4)0.0167 (17)
O1W0.2775 (5)1.2846 (9)0.0055 (5)0.057 (3)0.800
H4A0.580900.413300.127900.0310*0.630
H5A0.436300.284400.131100.0270*0.630
H6A0.322100.200100.207800.0360*0.630
H7A0.319100.224700.359000.0310*0.630
H8A0.431100.336900.435700.0310*0.630
H1A0.569600.448300.425600.0240*0.630
H2A0.683200.539800.359900.0300*0.630
H3A0.692900.515300.207300.0220*0.630
H1B0.489600.349400.441500.0260*0.370
H2B0.366100.263100.419600.0330*0.370
H3B0.314500.212800.281000.0350*0.370
H4B0.402100.264400.163400.0240*0.370
H5B0.538000.366300.111400.0380*0.370
H6B0.668900.463800.143400.0360*0.370
H7B0.706900.547900.284600.0270*0.370
H8B0.618400.494500.400800.0250*0.370
H20.710101.032900.281900.0320*
H30.681900.996500.134500.0280*
H40.554000.888400.091300.0270*
H60.319400.714700.254400.0220*
H80.541900.923300.457900.0390*
H11W0.307001.183900.018100.0850*0.800
H12W0.286001.394900.033100.0850*0.800
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
I70.0229 (2)0.0360 (2)0.0189 (2)0.0052 (2)0.0053 (2)0.0028 (2)
S50.0250 (8)0.0290 (8)0.0156 (6)0.0017 (8)0.0034 (6)0.0023 (7)
O80.025 (2)0.036 (2)0.0184 (18)0.0057 (18)0.006 (3)0.007 (3)
O510.030 (3)0.043 (3)0.025 (2)0.017 (2)0.010 (2)0.003 (2)
O520.028 (3)0.031 (3)0.025 (2)0.000 (2)0.003 (2)0.010 (2)
O530.045 (3)0.031 (3)0.021 (2)0.006 (3)0.000 (2)0.009 (2)
N10.017 (3)0.022 (3)0.027 (3)0.005 (2)0.003 (2)0.001 (3)
C20.018 (3)0.023 (4)0.041 (4)0.002 (3)0.007 (3)0.007 (3)
C30.018 (3)0.017 (3)0.035 (4)0.006 (3)0.005 (3)0.003 (3)
C40.028 (4)0.016 (3)0.023 (3)0.005 (3)0.004 (3)0.004 (3)
C50.025 (3)0.008 (3)0.012 (3)0.000 (2)0.001 (2)0.000 (2)
C60.018 (3)0.019 (3)0.018 (3)0.003 (3)0.002 (2)0.004 (3)
C70.013 (3)0.011 (3)0.020 (3)0.001 (2)0.006 (2)0.001 (2)
C80.020 (3)0.014 (3)0.018 (3)0.001 (2)0.001 (3)0.004 (3)
C90.013 (3)0.009 (3)0.025 (3)0.000 (2)0.001 (2)0.001 (2)
C100.018 (3)0.012 (3)0.020 (3)0.001 (2)0.000 (3)0.008 (3)
O1W0.070 (5)0.027 (4)0.073 (5)0.023 (4)0.034 (4)0.010 (4)
Geometric parameters (Å, º) top
I7—C72.078 (6)C8A—C9A1.38 (2)
S5—O521.454 (5)C8B—C9B1.40 (3)
S5—O511.447 (5)C9A—C10A1.48 (2)
S5—O531.462 (5)C9B—C10B1.31 (3)
S5—C51.776 (6)C2A—H2A0.9300
O8—C81.344 (8)C2B—H2B0.9300
O8—H80.8100C3A—H3A0.9300
O1W—H12W0.9000C3B—H3B0.9300
O1W—H11W0.8900C4A—H4A0.9300
N1A—C2A1.331 (17)C4B—H4B0.9300
N1A—C9A1.374 (16)C5A—H5A0.9300
N1B—C9B1.37 (3)C5B—H5B0.9300
N1B—C2B1.28 (3)C6A—H6A0.9300
N1A—H1A0.8600C6B—H6B0.9300
N1B—H1B0.8600C7A—H7A0.9300
N1—C21.326 (9)C7B—H7B0.9300
N1—C91.351 (8)C8A—H8A0.9300
C2A—C3A1.409 (19)C8B—H8B0.9300
C2B—C3B1.39 (3)C2—C31.401 (11)
C3A—C4A1.374 (17)C3—C41.371 (9)
C3B—C4B1.34 (3)C4—C101.404 (9)
C4A—C10A1.37 (2)C5—C61.380 (9)
C4B—C10B1.45 (3)C5—C101.424 (9)
C5A—C10A1.37 (2)C6—C71.412 (9)
C5A—C6A1.371 (18)C7—C81.372 (9)
C5B—C6B1.35 (3)C8—C91.425 (9)
C5B—C10B1.46 (3)C9—C101.434 (9)
C6A—C7A1.39 (2)C2—H20.9300
C6B—C7B1.41 (3)C3—H30.9300
C7A—C8A1.37 (2)C4—H40.9300
C7B—C8B1.36 (3)C6—H60.9300
O51—S5—O52113.9 (3)C4B—C3B—H3B122.00
O51—S5—O53112.1 (3)C10A—C4A—H4A120.00
O51—S5—C5106.3 (3)C3A—C4A—H4A120.00
O52—S5—O53112.2 (3)C3B—C4B—H4B122.00
O52—S5—C5105.7 (3)C10B—C4B—H4B122.00
O53—S5—C5105.9 (3)C10A—C5A—H5A118.00
C8—O8—H8108.00C6A—C5A—H5A118.00
H11W—O1W—H12W122.00C10B—C5B—H5B122.00
C2A—N1A—C9A123.7 (10)C6B—C5B—H5B122.00
C2B—N1B—C9B121.9 (17)C5A—C6A—H6A120.00
C9A—N1A—H1A118.00C7A—C6A—H6A120.00
C2A—N1A—H1A118.00C5B—C6B—H6B119.00
C9B—N1B—H1B119.00C7B—C6B—H6B119.00
C2B—N1B—H1B119.00C8A—C7A—H7A119.00
C2—N1—C9117.6 (6)C6A—C7A—H7A119.00
N1A—C2A—C3A120.6 (12)C8B—C7B—H7B120.00
N1B—C2B—C3B125 (2)C6B—C7B—H7B120.00
C2A—C3A—C4A119.4 (11)C7A—C8A—H8A121.00
C2B—C3B—C4B117 (2)C9A—C8A—H8A122.00
C3A—C4A—C10A120.7 (13)C9B—C8B—H8B122.00
C3B—C4B—C10B116 (2)C7B—C8B—H8B122.00
C6A—C5A—C10A123.8 (14)N1—C2—C3124.0 (6)
C6B—C5B—C10B116 (2)C2—C3—C4119.0 (6)
C5A—C6A—C7A120.1 (12)C3—C4—C10119.6 (6)
C5B—C6B—C7B123 (2)C6—C5—C10120.7 (6)
C6A—C7A—C8A121.7 (12)S5—C5—C6117.1 (5)
C6B—C7B—C8B120.7 (19)S5—C5—C10122.2 (5)
C7A—C8A—C9A117.0 (12)C5—C6—C7121.6 (6)
C7B—C8B—C9B115.4 (19)I7—C7—C8119.9 (4)
C8A—C9A—C10A124.0 (13)I7—C7—C6120.1 (5)
N1A—C9A—C10A115.8 (12)C6—C7—C8120.0 (6)
N1A—C9A—C8A120.2 (11)O8—C8—C9120.4 (5)
N1B—C9B—C8B119.4 (17)O8—C8—C7120.2 (5)
C8B—C9B—C10B126 (2)C7—C8—C9119.5 (6)
N1B—C9B—C10B115 (2)N1—C9—C10122.8 (6)
C4A—C10A—C9A119.6 (15)C8—C9—C10121.3 (6)
C4A—C10A—C5A126.7 (16)N1—C9—C8115.8 (6)
C5A—C10A—C9A113.3 (14)C4—C10—C9117.0 (6)
C5B—C10B—C9B118 (2)C4—C10—C5126.1 (6)
C4B—C10B—C5B116 (2)C5—C10—C9116.9 (6)
C4B—C10B—C9B126 (2)N1—C2—H2118.00
C3A—C2A—H2A120.00C3—C2—H2118.00
N1A—C2A—H2A120.00C4—C3—H3121.00
C3B—C2B—H2B117.00C2—C3—H3120.00
N1B—C2B—H2B118.00C3—C4—H4120.00
C2A—C3A—H3A120.00C10—C4—H4120.00
C4A—C3A—H3A120.00C5—C6—H6119.00
C2B—C3B—H3B122.00C7—C6—H6119.00
O53—S5—C5—C6130.4 (5)C8A—C9A—C10A—C4A177.6 (14)
O53—S5—C5—C1051.8 (5)N1—C2—C3—C40.9 (10)
O52—S5—C5—C6110.4 (5)C2—C3—C4—C100.1 (9)
O51—S5—C5—C611.0 (5)C3—C4—C10—C5179.3 (6)
O51—S5—C5—C10171.1 (5)C3—C4—C10—C90.5 (9)
O52—S5—C5—C1067.4 (5)S5—C5—C6—C7177.8 (5)
C2A—N1A—C9A—C10A3.5 (18)C10—C5—C6—C70.0 (9)
C9A—N1A—C2A—C3A1.6 (17)S5—C5—C10—C41.5 (8)
C2A—N1A—C9A—C8A179.2 (11)S5—C5—C10—C9178.7 (4)
C9—N1—C2—C31.4 (9)C6—C5—C10—C4179.2 (6)
C2—N1—C9—C8179.6 (5)C6—C5—C10—C91.0 (8)
C2—N1—C9—C100.9 (9)C5—C6—C7—I7177.1 (4)
N1A—C2A—C3A—C4A1.3 (17)C5—C6—C7—C80.5 (9)
C2A—C3A—C4A—C10A3 (2)I7—C7—C8—O82.6 (7)
C3A—C4A—C10A—C5A178.0 (15)I7—C7—C8—C9177.6 (4)
C3A—C4A—C10A—C9A5 (2)C6—C7—C8—O8179.9 (5)
C6A—C5A—C10A—C4A176.6 (16)C6—C7—C8—C90.0 (8)
C6A—C5A—C10A—C9A4 (2)O8—C8—C9—N10.4 (8)
C10A—C5A—C6A—C7A1 (2)O8—C8—C9—C10179.1 (5)
C5A—C6A—C7A—C8A0.7 (19)C7—C8—C9—N1179.8 (5)
C6A—C7A—C8A—C9A0.3 (19)C7—C8—C9—C101.1 (9)
C7A—C8A—C9A—C10A2 (2)N1—C9—C10—C40.0 (9)
C7A—C8A—C9A—N1A179.1 (11)N1—C9—C10—C5179.8 (5)
N1A—C9A—C10A—C4A5 (2)C8—C9—C10—C4178.6 (6)
C8A—C9A—C10A—C5A4 (2)C8—C9—C10—C51.5 (8)
N1A—C9A—C10A—C5A179.0 (13)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N1A—H1A···O53i0.861.972.783 (10)157
N1B—H1B···O53i0.861.882.725 (16)166
O8—H8···N10.812.232.693 (7)117
O8—H8···O52ii0.812.132.769 (7)135
O1W—H11W···O520.892.183.066 (9)179
O1W—H12W···O51iii0.902.183.080 (8)178
C4—H4···O530.932.553.110 (8)119
C6—H6···O510.932.392.827 (8)108
C8A—H8A···O53i0.932.583.251 (14)130
Symmetry codes: (i) x+1, y+1, z+1/2; (ii) x+1, y+2, z+1/2; (iii) x, y+1, z.

Experimental details

Crystal data
Chemical formulaC9H8N+·C9H5INO4S·0.8H2O
Mr494.69
Crystal system, space groupOrthorhombic, Pca21
Temperature (K)200
a, b, c (Å)16.2403 (5), 7.1539 (3), 15.2458 (5)
V3)1771.28 (11)
Z4
Radiation typeMo Kα
µ (mm1)1.96
Crystal size (mm)0.32 × 0.25 × 0.12
Data collection
DiffractometerOxford Diffraction Gemini-S CCD-detector
diffractometer
Absorption correctionMulti-scan
(CrysAlis PRO; Agilent, 2012)
Tmin, Tmax0.906, 0.980
No. of measured, independent and
observed [I > 2σ(I)] reflections
6143, 3207, 2709
Rint0.028
(sin θ/λ)max1)0.680
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.040, 0.082, 1.18
No. of reflections3207
No. of parameters244
No. of restraints1
H-atom treatmentH-atom parameters constrained
Δρmax, Δρmin (e Å3)0.65, 0.66
Absolute structureFlack (1983), 789 Friedel pairs
Absolute structure parameter0.01 (3)

Computer programs: CrysAlis PRO (Agilent, 2012), SIR92 (Altomare et al., 1993), SHELXL97 (Sheldrick, 2008) within WinGX (Farrugia, 2012), PLATON (Spek, 2009).

Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N1A—H1A···O53i0.861.972.783 (10)157
N1B—H1B···O53i0.861.882.725 (16)166
O8—H8···O52ii0.812.132.769 (7)135
O1W—H11W···O520.892.183.066 (9)179
O1W—H12W···O51iii0.902.183.080 (8)178
Symmetry codes: (i) x+1, y+1, z+1/2; (ii) x+1, y+2, z+1/2; (iii) x, y+1, z.
 

Acknowledgements

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

References

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First citationVogel, A. I. (1964). Textbook of Macro and Semi-Micro Qualitative Inorganic Analysis, 4th ed., p. 266. London: Longmans.

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