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In the title compound, C10H9N2+·C9H5INO4S·2H2O, the 4,4′-bi­pyridine mol­ecule is protonated at one of the pyridine N atoms. These moieties self-assemble into a supramolecular chain along the a axis through N—H...N hydrogen bonds. The quinolinol OH group acts as a donor with respect to a sulfonate O atom [O—H...O(sulfonate)] and acts as an acceptor with respect to a C—H group of ferron [C—H...O(hydroxy)], forming a supramolecular chain along the b axis. These two types of supramolecular chains (one type made up of bi­pyridine motifs and the other made up of sulfoxine motifs) interact via π–π stacking, generating a three-dimensional framework. These chains are further crosslinked by C—­H...O hydrogen bonds and O—H...O hydrogen bonds involving water mol­ecules.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S0108270104001295/de1227sup1.cif
Contains datablocks global, I

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S0108270104001295/de1227Isup2.hkl
Contains datablock I

CCDC reference: 200584

Comment top

Derivatives of 8-hydroxyquinoline (oxine) are known for their antiamoebic, antibacterial and antifungal activities, which are correlated to their metal-chelating ability (Banerjee & Saha, 1986). The introduction of sulfonic acid into the oxine moiety offers additional metal-binding and hydrogen-bonding sites/modes. This type of ligand is called sulfoxine (sulfonic acid + oxine). Hydrogen bonds are primarily electrostatic and are formed with both strong and weak donors and acceptors (Desiraju & Steiner, 1999). Hydrogen-bonding patterns and metal-binding modes of sulfoxinates are of current interest (Cai, Chen, Liao et al., 2001; Cai, Chen, Feng et al., 2001). The crystal structures of 8-hydroxy-7-iodoquinoline-5-sulfonic acid (ferron; Balasubramanian & Muthiah, 1996), a cobalt complex of ferron (Balasubramanian, 1995), a nickel(II) complex of ferron (Raj et al., 2003) and a zinc(II) complex of ferron (Francis et al., 2003) have recently been reported from our laboratory. 4,4'-Bipyridine is an excellent synthon in preparing novel supramolecular structures, owing to its rigidity and aptness to form strong hydrogen bonds/coordination bonds via its two N atoms. The supramolecular structures made up of many 4,4'-bipyridine have been reported (Lough et al., 2000). In this paper, the hydrogen-bonding patterns of 4,4'-bipyridinium 8-hydroxy-7-iodoquinoline-5-sulfonate dihydrate, (I), are discussed.

The asymmetric unit of (I) contains one 4,4'-bipyridinium cation, a 8-hydroxy-7-iodoquinoline-5-sulfonate (ferron) anion, and two water molecules (Fig. 1). The bipyridine moiety is protonated at one of the ring N atoms (N1A), as is evident from the increase of the internal angle at nitrogen (C2A—N1A—C6A) from 115.45 (19)° in neutral 4,4'-bipyridine (Boag et al., 1999) to 121.5 (5)° in the present study. This increase of the internal angle has also been observed in many 4,4'-bipyridinium salts (Iyere et al., 2002). In the 4,4'-bipyridinium cation, the two rings are twisted by 31.05(X)° about the C7A—C4A bond; this angle normally ranges from 17 (1) to 38.4 (9)° (Subbotin & Aslanov, 1986). The sulfonic acid group is deprotonated. In the 8-hydroxy-7-iodoquinoline system, the hydroxy H atom forms an intramolecular hydrogen bond with the quinoline N atom, leading to a hydrogen-bonded ring with graph-set notation S(5), as also observed in the neutral 8-hydroxyquinoline system. The quinolinol O1 atom is hydrogen bonded to the sulfonate O3 atom and the C4 atom of a screw-related ligand; it is also hydrogen bonded to the quinolinol oxygen (O1), forming a hydrogen-bonded ring, with graph-set notation R22(8) (Etter, 1990; Bernstein et al., 1995). The 4,4'-bipyridinium moieties self-assemble into a supramolecular chain along the a axis through N—H···N hydrogen bonds involving the protonated and the unprotonated N atoms. These two types of supramolecular chains (one type made up of bipyridine motifs and the other made up of sulfoxine motifs) interact via ππ stacking, generating a three-dimensional framework. These chains are further crosslinked by C—H···O and O—H···O hydrogen bonds involving water molecules (Table 2 and Fig 2).

In the structure of (I), ππ interactions between the aromatic rings are observed. The N1/C2–C4/C9/C10 pyridine ring of ferron has stacking interactions with the N1A/C2A–C6A pyridine ring of the 4,4'-bipyridinium cation, with a perpendicular separation of 3.498(X)Å, a centroid-to-centroid distance of 3.653 (3) Å and a slip angle (the angle between the centroid vector and the normal to the plane) of 16.48(X)°. The C5–C10 phenyl ring of ferron is positioned over the N1A/C2A–C6A pyridine ring of the 4,4'-bipyridinium cation, with a perpendicular separation of 3.521(X)Å, a centroid-to-centroid distance of 3.813 (3) Å and a slip angle of 31.23(X)°. These values are close to those reported for aromatic ππ stacking interactions (Hunter, 1994). The I1 atom is in contact with the sulfonate O4 atom [I1···O4(-x, y + 1/2, −z + 1/2) = 3.105 (4) Å; van der Waals distance = 3.50 Å; C7—I1···O4 = 172.2(X)°]; this I···O interaction was also observed in the crystal structure of ferron (Balasubramanian & Muthiah, 1996). This type of halogen–oxygen interaction has been recognized in the literature and is widely used in crystal engineering (Thalladi et al., 1996).

Experimental top

Hot aqueous solutions of 4,4'-bipyridine (39.05 mg) and ferron (87.80 mg) were mixed in a 1:1 molar ratio. The resulting solution was warmed over a water bath for half an hour and kept at room temperature for crystallization. After a few days, plate-like yellow crystals were obtained.

Refinement top

One of the H atoms (H11W) of water molecule O1W and one of the H atoms (H22W) of water molecule O2W were located from a difference Fourier map and allowed for but not refined in subsequent calculations. The remaining H atom of each water molecule could not be located. All other H atoms were refined using a riding model; Uiso values were set at 1.2eq(parent). The various O···O interactions are as follows: O1W···O1W(-x + 1, −y, −z) = 2.8164 (7) Å, O1W···O2W(-x + 1, y − 1/2, −z + 1/2) = 2.8113 (7) Å and O2W···O2W(-x + 2, −y + 1, −z + 1) = 2.7961 (8) Å.

Computing details top

Data collection: FEBO (Belleti, 1996); cell refinement: MolEN (Fair, 1990); data reduction: MolEN; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: PLATON97 (Spek, 1997); software used to prepare material for publication: PLATON97.

Figures top
[Figure 1] Fig. 1. A view of the components of (I), with the atom-labelling scheme and 50% probability displacement ellipsoids.
[Figure 2] Fig. 2. The hydrogen-bonding patterns in (I).
4,4'-bipyridinium 8-hydroxy-7-iodoquinoline-5-sulfonate dihydrate top
Crystal data top
C10H9N2+·C9H5INO4S·2H2OF(000) = 1072
Mr = 541.32Dx = 1.735 Mg m3
Monoclinic, P21/cMo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybcCell parameters from 25 reflections
a = 9.657 (3) Åθ = 3.0–27.0°
b = 15.213 (3) ŵ = 1.69 mm1
c = 14.679 (2) ÅT = 293 K
β = 106.01 (3)°Plate, yellow
V = 2072.9 (9) Å30.29 × 0.20 × 0.19 mm
Z = 4
Data collection top
Philips PW 1100
diffractometer
Rint = 0.065
Radiation source: fine-focus sealed tubeθmax = 27.0°, θmin = 3.0°
Graphite monochromatorh = 1211
ω scansk = 019
4690 measured reflectionsl = 018
4526 independent reflections1 standard reflections every 100 reflections
3101 reflections with I > 2σ(I) intensity decay: none
Refinement top
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.057Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.152H-atom parameters constrained
S = 0.97 w = 1/[σ2(Fo2) + (0.0974P)2
where P = (Fo2 + 2Fc2)/3
4526 reflections(Δ/σ)max < 0.001
272 parametersΔρmax = 2.43 e Å3
0 restraintsΔρmin = 2.49 e Å3
Crystal data top
C10H9N2+·C9H5INO4S·2H2OV = 2072.9 (9) Å3
Mr = 541.32Z = 4
Monoclinic, P21/cMo Kα radiation
a = 9.657 (3) ŵ = 1.69 mm1
b = 15.213 (3) ÅT = 293 K
c = 14.679 (2) Å0.29 × 0.20 × 0.19 mm
β = 106.01 (3)°
Data collection top
Philips PW 1100
diffractometer
Rint = 0.065
4690 measured reflections1 standard reflections every 100 reflections
4526 independent reflections intensity decay: none
3101 reflections with I > 2σ(I)
Refinement top
R[F2 > 2σ(F2)] = 0.0570 restraints
wR(F2) = 0.152H-atom parameters constrained
S = 0.97Δρmax = 2.43 e Å3
4526 reflectionsΔρmin = 2.49 e Å3
272 parameters
Special details top

Geometry. Bond distances, angles etc. have been calculated using the rounded fractional coordinates. All e.s.d.'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 on F2 for ALL reflections except those flagged by the user for potential systematic errors. Weighted R-factors wR and all goodnesses of fit S are based on F2, conventional R-factors R are based on F, with F set to zero for negative F2. The observed criterion of F2 > σ(F2) is used only for calculating -R-factor-obs 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*/Ueq
I10.08594 (4)0.38215 (2)0.21492 (3)0.0414 (1)
S20.27537 (14)0.02379 (8)0.25072 (10)0.0320 (4)
O10.3959 (5)0.3968 (2)0.1775 (4)0.0483 (14)
O20.3026 (5)0.0260 (3)0.1742 (3)0.0493 (16)
O30.3712 (5)0.0013 (3)0.3429 (3)0.0448 (12)
O40.1246 (4)0.0242 (3)0.2502 (3)0.0436 (14)
N10.6050 (5)0.2779 (3)0.1862 (3)0.0376 (16)
C20.7075 (6)0.2200 (4)0.1906 (4)0.0412 (19)
C30.6962 (6)0.1316 (4)0.2090 (4)0.0397 (19)
C40.5705 (6)0.0992 (4)0.2225 (4)0.0365 (17)
C50.3167 (5)0.1352 (3)0.2293 (4)0.0290 (16)
C60.2157 (6)0.1988 (3)0.2264 (4)0.0313 (17)
C70.2421 (6)0.2881 (3)0.2109 (4)0.0317 (17)
C80.3712 (6)0.3119 (3)0.1956 (4)0.0333 (17)
C90.4790 (5)0.2479 (3)0.1990 (4)0.0296 (17)
C100.4545 (5)0.1585 (3)0.2176 (4)0.0291 (16)
N1A0.4789 (4)0.2124 (3)0.4575 (3)0.0391 (16)
N10A1.2034 (5)0.2090 (4)0.4578 (3)0.0431 (16)
C2A0.5366 (6)0.2850 (4)0.4338 (4)0.042 (2)
C3A0.6773 (6)0.2862 (4)0.4316 (4)0.0368 (17)
C4A0.7612 (5)0.2105 (3)0.4550 (4)0.0298 (16)
C5A0.6987 (6)0.1366 (4)0.4815 (4)0.0383 (19)
C6A0.5560 (6)0.1393 (4)0.4821 (5)0.0418 (19)
C7A0.9151 (5)0.2099 (4)0.4541 (4)0.0308 (16)
C8A0.9803 (6)0.1342 (4)0.4341 (4)0.0395 (19)
C9A1.1231 (6)0.1360 (4)0.4368 (4)0.0429 (19)
C11A1.1404 (6)0.2823 (4)0.4756 (5)0.048 (2)
C12A0.9971 (6)0.2859 (4)0.4747 (5)0.0427 (19)
O1W0.3631 (5)0.0293 (3)0.0032 (3)0.0601 (17)
O2W0.9254 (5)0.4751 (4)0.5651 (3)0.0699 (19)
H10.482900.406100.192900.0580*
H20.793300.239800.180800.0500*
H30.773500.094100.212200.0480*
H40.561300.039700.234600.0440*
H60.127100.182900.234800.0380*
H1A0.389600.212500.456900.0470*
H2A0.480900.335500.418500.0500*
H3A0.717000.337200.414600.0440*
H5A0.752200.085500.498800.0470*
H6A0.513500.089700.499900.0500*
H8A0.927700.082400.419300.0480*
H9A1.165900.084700.423300.0520*
H11A1.195100.333400.489300.0580*
H12A0.956400.338200.487700.0510*
H11W0.377900.010500.053800.0480*
H22W0.965400.483500.630900.0480*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
I10.0318 (2)0.0336 (2)0.0554 (3)0.0072 (2)0.0065 (2)0.0018 (2)
S20.0277 (6)0.0247 (6)0.0419 (8)0.0047 (5)0.0068 (6)0.0000 (6)
O10.037 (2)0.025 (2)0.082 (3)0.0042 (17)0.015 (2)0.001 (2)
O20.058 (3)0.035 (2)0.060 (3)0.006 (2)0.025 (2)0.010 (2)
O30.041 (2)0.037 (2)0.048 (2)0.0031 (18)0.0016 (19)0.0074 (18)
O40.0228 (19)0.041 (2)0.067 (3)0.0124 (17)0.0126 (18)0.004 (2)
N10.033 (3)0.031 (2)0.047 (3)0.0102 (19)0.008 (2)0.002 (2)
C20.027 (3)0.046 (3)0.052 (4)0.005 (2)0.013 (3)0.004 (3)
C30.024 (3)0.046 (3)0.048 (4)0.005 (2)0.008 (2)0.001 (3)
C40.027 (3)0.033 (3)0.046 (3)0.000 (2)0.004 (2)0.001 (2)
C50.021 (2)0.028 (3)0.034 (3)0.005 (2)0.001 (2)0.002 (2)
C60.025 (3)0.031 (3)0.037 (3)0.002 (2)0.007 (2)0.002 (2)
C70.026 (3)0.028 (3)0.037 (3)0.002 (2)0.002 (2)0.003 (2)
C80.030 (3)0.028 (3)0.038 (3)0.009 (2)0.003 (2)0.007 (2)
C90.026 (3)0.029 (3)0.032 (3)0.005 (2)0.005 (2)0.005 (2)
C100.023 (2)0.029 (3)0.032 (3)0.002 (2)0.002 (2)0.001 (2)
N1A0.012 (2)0.058 (3)0.044 (3)0.000 (2)0.0021 (18)0.003 (2)
N10A0.018 (2)0.064 (3)0.045 (3)0.000 (2)0.005 (2)0.001 (3)
C2A0.021 (3)0.049 (4)0.050 (4)0.010 (3)0.002 (2)0.002 (3)
C3A0.021 (3)0.037 (3)0.050 (3)0.001 (2)0.006 (2)0.004 (3)
C4A0.014 (2)0.035 (3)0.038 (3)0.000 (2)0.003 (2)0.002 (2)
C5A0.023 (3)0.036 (3)0.056 (4)0.004 (2)0.011 (3)0.002 (3)
C6A0.024 (3)0.047 (3)0.054 (4)0.008 (2)0.010 (3)0.001 (3)
C7A0.014 (2)0.039 (3)0.037 (3)0.000 (2)0.003 (2)0.002 (2)
C8A0.022 (3)0.046 (3)0.050 (4)0.001 (2)0.009 (2)0.004 (3)
C9A0.023 (3)0.057 (4)0.046 (3)0.013 (3)0.005 (2)0.001 (3)
C11A0.026 (3)0.057 (4)0.058 (4)0.012 (3)0.008 (3)0.006 (3)
C12A0.021 (3)0.042 (3)0.063 (4)0.001 (2)0.008 (3)0.004 (3)
O1W0.040 (3)0.079 (3)0.059 (3)0.003 (2)0.010 (2)0.010 (3)
O2W0.046 (3)0.095 (4)0.059 (3)0.012 (3)0.002 (2)0.019 (3)
Geometric parameters (Å, º) top
I1—C72.091 (5)C8—C91.416 (7)
S2—O21.438 (5)C9—C101.420 (7)
S2—O31.454 (5)C2—H20.9294
S2—O41.454 (4)C3—H30.9304
S2—C51.789 (5)C4—H40.9314
O1—C81.353 (6)C6—H60.9295
O1—H10.8199C2A—C3A1.368 (9)
O1W—H11W0.9382C3A—C4A1.395 (8)
O2W—H22W0.9448C4A—C7A1.490 (7)
N1—C91.360 (7)C4A—C5A1.382 (8)
N1—C21.313 (8)C5A—C6A1.381 (9)
N1A—C2A1.326 (8)C7A—C12A1.387 (8)
N1A—C6A1.332 (8)C7A—C8A1.382 (8)
N10A—C9A1.341 (8)C8A—C9A1.369 (9)
N10A—C11A1.330 (8)C11A—C12A1.381 (9)
N1A—H1A0.8600C2A—H2A0.9292
C2—C31.382 (9)C3A—H3A0.9295
C3—C41.374 (9)C5A—H5A0.9292
C4—C101.425 (8)C6A—H6A0.9302
C5—C101.433 (7)C8A—H8A0.9302
C5—C61.366 (7)C9A—H9A0.9297
C6—C71.412 (7)C11A—H11A0.9302
C7—C81.375 (8)C12A—H12A0.9302
I1···O13.197 (5)C6···C9Aiii3.574 (8)
I1···O4i3.105 (4)C6···C11Av3.562 (9)
I1···H22Wii3.1881C6···N10Aiii3.435 (7)
S2···H42.8459C6A···O33.123 (8)
S2···H9Aiii3.1418C6A···N1xiii3.163 (8)
S2···H1iv2.8765C6A···O3x3.267 (8)
S2···H22Wv3.0269C7···C11Av3.489 (9)
O1···I13.197 (5)C8···N10Av3.434 (7)
O1···N12.688 (6)C8···C2A3.444 (8)
O1···O3vi2.837 (7)C9···C3A3.472 (8)
O1···C4vi3.388 (7)C9···C2A3.384 (8)
O1W···O2Wiv2.812 (7)C9A···O4xiv3.228 (7)
O1W···O1Wvii2.816 (7)C9A···C6xiv3.574 (8)
O1W···O22.856 (6)C11A···C7viii3.489 (9)
O2···O1W2.856 (6)C11A···C6viii3.562 (9)
O2···C3Aiv3.283 (8)C12A···O2W3.321 (9)
O2···C43.132 (8)C3A···H12A2.7100
O2W···O4viii2.864 (6)C5A···H8A2.7419
O2W···O1Wvi2.812 (7)C8A···H5A2.7308
O2W···O2Wix2.797 (7)C9A···H6xiv3.0604
O2W···C12A3.321 (9)C9A···H1Axiv2.7651
O3···C6Ax3.267 (8)C11A···H1Axiv2.7127
O3···C43.305 (8)C12A···H3A2.7180
O3···C6A3.123 (8)H1···O2vi2.6333
O3···O1iv2.837 (7)H1···S2vi2.8765
O4···C9Aiii3.228 (7)H1···N12.2951
O4···I1xi3.105 (4)H1···O3vi2.1834
O4···O2Wv2.864 (6)H1···H4vi2.3867
O1···H4vi2.5035H1A···C9Aiii2.7651
O1W···H11Av2.6180H1A···N10Aiii1.8026
O1W···H2Axii2.8019H1A···C11Aiii2.7127
O1W···H11Wvii2.8622H2A···O1Wxiii2.8019
O2···H42.6086H3A···O2vi2.4352
O2···H11W2.1016H3A···H12A2.2645
O2···H3Aiv2.4352H3A···H11Wvi2.5803
O2···H1iv2.6333H3A···C12A2.7180
O2W···H12A2.4301H4···O1iv2.5035
O3···H42.8015H4···H1iv2.3867
O3···H6Ax2.6578H4···O22.6086
O3···H9Aiii2.8677H4···O32.8015
O3···H6A2.6947H4···S22.8459
O3···H1iv2.1834H5A···C8A2.7308
O4···H9Aiii2.6275H5A···H8A2.3081
O4···H22Wv1.9897H6···C9Aiii3.0604
O4···H62.4256H6···O42.4256
N1···N1Axii3.243 (6)H6A···O3x2.6578
N1···C6Axii3.163 (8)H6A···O32.6947
N1···O12.688 (6)H8A···C5A2.7419
N1A···N1xiii3.243 (6)H8A···H5A2.3081
N1A···N10Aiii2.662 (6)H9A···S2xiv3.1418
N10A···C6xiv3.435 (7)H9A···O3xiv2.8677
N10A···N1Axiv2.662 (6)H9A···O4xiv2.6275
N10A···C8viii3.434 (7)H11A···O1Wviii2.6180
N1···H12.2951H11W···O22.1016
N10A···H1Axiv1.8026H11W···H3Aiv2.5803
C2A···C83.444 (8)H11W···O1Wvii2.8622
C2A···C93.384 (8)H12A···H3A2.2645
C3A···C93.472 (8)H12A···O2W2.4301
C3A···O2vi3.283 (8)H12A···C3A2.7100
C4···O1iv3.388 (7)H22W···I1ii3.1881
C4···O23.132 (8)H22W···S2viii3.0269
C4···O33.305 (8)H22W···O4viii1.9897
O2—S2—O3113.4 (3)C3—C4—H4120.70
O2—S2—O4113.4 (3)C10—C4—H4120.67
O2—S2—C5105.3 (3)C5—C6—H6119.14
O3—S2—O4112.7 (3)C7—C6—H6119.04
O3—S2—C5105.7 (3)N1A—C2A—C3A120.6 (5)
O4—S2—C5105.5 (3)C2A—C3A—C4A119.7 (5)
C8—O1—H1109.47C3A—C4A—C7A121.0 (5)
C2—N1—C9117.3 (5)C3A—C4A—C5A118.1 (5)
C2A—N1A—C6A121.5 (5)C5A—C4A—C7A120.8 (5)
C9A—N10A—C11A118.2 (5)C4A—C5A—C6A119.5 (5)
C6A—N1A—H1A119.23N1A—C6A—C5A120.5 (5)
C2A—N1A—H1A119.25C8A—C7A—C12A118.3 (5)
N1—C2—C3124.3 (6)C4A—C7A—C8A121.4 (5)
C2—C3—C4119.9 (6)C4A—C7A—C12A120.3 (5)
C3—C4—C10118.6 (5)C7A—C8A—C9A119.4 (6)
S2—C5—C6119.0 (4)N10A—C9A—C8A122.5 (6)
S2—C5—C10121.0 (4)N10A—C11A—C12A122.9 (6)
C6—C5—C10120.0 (4)C7A—C12A—C11A118.6 (6)
C5—C6—C7121.8 (5)N1A—C2A—H2A119.67
C6—C7—C8119.5 (5)C3A—C2A—H2A119.72
I1—C7—C8121.2 (3)C2A—C3A—H3A120.22
I1—C7—C6119.3 (4)C4A—C3A—H3A120.03
O1—C8—C7120.0 (5)C4A—C5A—H5A120.30
O1—C8—C9119.7 (5)C6A—C5A—H5A120.25
C7—C8—C9120.3 (4)N1A—C6A—H6A119.78
N1—C9—C8116.2 (4)C5A—C6A—H6A119.74
N1—C9—C10123.4 (5)C7A—C8A—H8A120.26
C8—C9—C10120.4 (5)C9A—C8A—H8A120.30
C4—C10—C9116.5 (5)N10A—C9A—H9A118.77
C5—C10—C9118.0 (4)C8A—C9A—H9A118.72
C4—C10—C5125.5 (5)N10A—C11A—H11A118.67
N1—C2—H2117.85C12A—C11A—H11A118.46
C3—C2—H2117.87C7A—C12A—H12A120.64
C2—C3—H3120.07C11A—C12A—H12A120.72
C4—C3—H3120.08
O2—S2—C5—C6126.6 (5)C6—C7—C8—C92.4 (8)
O2—S2—C5—C1054.9 (5)I1—C7—C8—C9176.1 (4)
O3—S2—C5—C6113.1 (5)O1—C8—C9—N11.9 (8)
O3—S2—C5—C1065.4 (5)C7—C8—C9—C100.4 (8)
O4—S2—C5—C66.5 (5)O1—C8—C9—C10179.8 (5)
O4—S2—C5—C10175.1 (5)C7—C8—C9—N1177.8 (5)
C2—N1—C9—C8178.9 (5)C8—C9—C10—C4178.2 (5)
C9—N1—C2—C31.2 (8)C8—C9—C10—C52.1 (8)
C2—N1—C9—C100.7 (8)N1—C9—C10—C5179.7 (5)
C6A—N1A—C2A—C3A1.7 (8)N1—C9—C10—C40.0 (8)
C2A—N1A—C6A—C5A1.5 (9)N1A—C2A—C3A—C4A0.4 (9)
C9A—N10A—C11A—C12A1.0 (9)C2A—C3A—C4A—C5A1.1 (8)
C11A—N10A—C9A—C8A0.7 (8)C2A—C3A—C4A—C7A179.5 (5)
N1—C2—C3—C41.1 (9)C3A—C4A—C5A—C6A1.3 (9)
C2—C3—C4—C100.4 (8)C7A—C4A—C5A—C6A179.7 (6)
C3—C4—C10—C90.1 (8)C3A—C4A—C7A—C8A150.1 (6)
C3—C4—C10—C5179.5 (5)C3A—C4A—C7A—C12A30.7 (8)
S2—C5—C10—C9178.8 (4)C5A—C4A—C7A—C8A31.6 (8)
S2—C5—C10—C40.8 (8)C5A—C4A—C7A—C12A147.6 (6)
S2—C5—C6—C7179.3 (4)C4A—C5A—C6A—N1A0.1 (9)
C10—C5—C6—C70.8 (9)C12A—C7A—C8A—C9A1.1 (9)
C6—C5—C10—C92.7 (8)C4A—C7A—C12A—C11A178.3 (6)
C6—C5—C10—C4177.6 (6)C4A—C7A—C8A—C9A178.1 (5)
C5—C6—C7—I1176.7 (4)C8A—C7A—C12A—C11A0.9 (9)
C5—C6—C7—C81.9 (9)C7A—C8A—C9A—N10A0.3 (9)
C6—C7—C8—O1177.8 (5)N10A—C11A—C12A—C7A0.2 (10)
I1—C7—C8—O13.7 (8)
Symmetry codes: (i) x, y+1/2, z+1/2; (ii) x+1, y+1, z+1; (iii) x1, y, z; (iv) x+1, y1/2, z+1/2; (v) x1, y+1/2, z1/2; (vi) x+1, y+1/2, z+1/2; (vii) x+1, y, z; (viii) x+1, y+1/2, z+1/2; (ix) x+2, y+1, z+1; (x) x+1, y, z+1; (xi) x, y1/2, z+1/2; (xii) x, y+1/2, z1/2; (xiii) x, y+1/2, z+1/2; (xiv) x+1, y, z.
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
O1—H1···N10.822.302.688 (6)110
O1—H1···O3vi0.822.182.837 (7)137
N1A—H1A···N10Aiii0.861.802.662 (6)178
O1W—H11W···O20.942.102.856 (6)137
O2W—H22W···O4viii0.941.992.864 (6)153
C3A—H3A···O2vi0.932.443.283 (8)152
C4—H4···O1iv0.932.503.388 (7)159
C6—H6···O40.932.432.850 (7)108
C12A—H12A···O2W0.932.433.321 (9)160
Symmetry codes: (iii) x1, y, z; (iv) x+1, y1/2, z+1/2; (vi) x+1, y+1/2, z+1/2; (viii) x+1, y+1/2, z+1/2.

Experimental details

Crystal data
Chemical formulaC10H9N2+·C9H5INO4S·2H2O
Mr541.32
Crystal system, space groupMonoclinic, P21/c
Temperature (K)293
a, b, c (Å)9.657 (3), 15.213 (3), 14.679 (2)
β (°) 106.01 (3)
V3)2072.9 (9)
Z4
Radiation typeMo Kα
µ (mm1)1.69
Crystal size (mm)0.29 × 0.20 × 0.19
Data collection
DiffractometerPhilips PW 1100
diffractometer
Absorption correction
No. of measured, independent and
observed [I > 2σ(I)] reflections
4690, 4526, 3101
Rint0.065
(sin θ/λ)max1)0.639
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.057, 0.152, 0.97
No. of reflections4526
No. of parameters272
H-atom treatmentH-atom parameters constrained
Δρmax, Δρmin (e Å3)2.43, 2.49

Computer programs: FEBO (Belleti, 1996), MolEN (Fair, 1990), MolEN, SHELXS97 (Sheldrick, 1997), SHELXL97 (Sheldrick, 1997), PLATON97 (Spek, 1997), PLATON97.

Selected geometric parameters (Å, º) top
I1—C72.091 (5)N1—C91.360 (7)
S2—O21.438 (5)N1—C21.313 (8)
S2—O31.454 (5)N1A—C2A1.326 (8)
S2—O41.454 (4)N1A—C6A1.332 (8)
S2—C51.789 (5)N10A—C9A1.341 (8)
O1—C81.353 (6)N10A—C11A1.330 (8)
O2—S2—O3113.4 (3)S2—C5—C10121.0 (4)
O2—S2—O4113.4 (3)I1—C7—C8121.2 (3)
O2—S2—C5105.3 (3)I1—C7—C6119.3 (4)
O3—S2—O4112.7 (3)O1—C8—C7120.0 (5)
O3—S2—C5105.7 (3)O1—C8—C9119.7 (5)
O4—S2—C5105.5 (3)N1—C9—C8116.2 (4)
C2—N1—C9117.3 (5)N1—C9—C10123.4 (5)
C2A—N1A—C6A121.5 (5)N1A—C2A—C3A120.6 (5)
C9A—N10A—C11A118.2 (5)N1A—C6A—C5A120.5 (5)
N1—C2—C3124.3 (6)N10A—C9A—C8A122.5 (6)
S2—C5—C6119.0 (4)N10A—C11A—C12A122.9 (6)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
O1—H1···N10.822.302.688 (6)110
O1—H1···O3i0.822.182.837 (7)137
N1A—H1A···N10Aii0.861.802.662 (6)178
O1W—H11W···O20.942.102.856 (6)137
O2W—H22W···O4iii0.941.992.864 (6)153
C3A—H3A···O2i0.932.443.283 (8)152
C4—H4···O1iv0.932.503.388 (7)159
C6—H6···O40.932.432.850 (7)108
C12A—H12A···O2W0.932.433.321 (9)160
Symmetry codes: (i) x+1, y+1/2, z+1/2; (ii) x1, y, z; (iii) x+1, y+1/2, z+1/2; (iv) x+1, y1/2, z+1/2.
 

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