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Acta Crystallogr Sect E Struct Rep Online. 2008 June 1; 64(Pt 6): o1109.
Published online 2008 May 17. doi:  10.1107/S1600536808014098
PMCID: PMC2961594

3-Amino­pyridinium 4-hydr­oxy-3-iodo­naphthalene-1-sulfonate dihydrate

Yun Liua and Jie Lia,*

Abstract

In the hydrated title salt, C5H7N2 +·C10H6IO4S·2H2O, the component species are linked by O—H(...)O and N—H(...)O hydrogen bonds, forming an infinite three-dimensional framework.

Related literature

For background, see: Li (2007 [triangle]).

An external file that holds a picture, illustration, etc.
Object name is e-64-o1109-scheme1.jpg

Experimental

Crystal data

  • C5H7N2 +·C10H6IO4S·2H2O
  • M r = 480.27
  • Monoclinic, An external file that holds a picture, illustration, etc.
Object name is e-64-o1109-efi1.jpg
  • a = 15.0219 (6) Å
  • b = 6.9917 (3) Å
  • c = 18.0729 (7) Å
  • β = 110.868 (1)°
  • V = 1773.66 (12) Å3
  • Z = 4
  • Mo Kα radiation
  • μ = 1.96 mm−1
  • T = 296 (2) K
  • 0.18 × 0.12 × 0.10 mm

Data collection

  • Bruker SMART APEX CCD diffractometer
  • Absorption correction: multi-scan (SADABS; Bruker, 2001 [triangle]) T min = 0.720, T max = 0.828
  • 17926 measured reflections
  • 3484 independent reflections
  • 3128 reflections with I > 2σ(I)
  • R int = 0.027

Refinement

  • R[F 2 > 2σ(F 2)] = 0.025
  • wR(F 2) = 0.069
  • S = 1.08
  • 3484 reflections
  • 258 parameters
  • 34 restraints
  • H atoms treated by a mixture of independent and constrained refinement
  • Δρmax = 0.70 e Å−3
  • Δρmin = −0.96 e Å−3

Data collection: SMART (Bruker, 2001 [triangle]); cell refinement: SAINT-Plus (Bruker, 2001 [triangle]); data reduction: SAINT-Plus; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 [triangle]); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 [triangle]); molecular graphics: PLATON (Spek, 2003 [triangle]); software used to prepare material for publication: PLATON.

Table 1
Hydrogen-bond geometry (Å, °)

Supplementary Material

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536808014098/hb2719sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536808014098/hb2719Isup2.hkl

Additional supplementary materials: crystallographic information; 3D view; checkCIF report

supplementary crystallographic information

Comment

This work continues our previous synthetic and structural studies of the hydrogen bonding interactions between various organic acids and substituted pyridines (Li, 2007).

The asymmetric unit of the title salt, (I), is composed of one 3-aminopyridinium cation, one 8-hydroxy-7-iodo-5-quinolinesulfonate anion and two water molecules (Fig. 1). One water molecule (O1W), acting as a hydrogen bonding donor interacts with the hydroxy oxygen (O4) acting as hydrogen bonding acceptor (Table 1). The other water molecule (O2W) and the 3-aminopyridinium cation are linked by a N1—H1A···O2W hydrogen bond. Moreover, the cation and anion are linked together by a N2—H2B···O1 hydrogen bond. Overall, an infinite three-dimensional framework results (Fig. 2).

Experimental

A 5-ml ethanol solution of 3-aminopyridine (1.0 mmol, 0.094 g) was added to a 20-ml hot aqueous solution of 8-hydroxy-7-iodo-5-quinolinesulfonic acid (1.0 mmol, 0.351 g) and the mixture was stirred for 20 minutes at 373 K. Then the solution was filtered, and the filtrate was kept at the room temperature. After two weeks, yellow blocks of (I) were obtained.

Refinement

The N- and O-bonded H atoms bonded were located in a difference synthesis and refined isotropically with N—H = 0.89 (1), O—H = 0.85 (1) and H···H = 1.34 (1) Å, respectively. All the remaining H atoms were placed in calculated positions, with C—H = 0.93Å and were refined as riding with Uiso = 1.2Ueq(C). This refinement scheme results in a short intramolecular H4···H6 contact of 1.71Å, although H4 participates in a plausible intermolecular hydrogen bond: thus the location of H4 should be regarded as less certain. Other placement schemes for H4 appear to lead to disordered hydrogen bond arrangements.

Figures

Fig. 1.
The molecular structure of (I). Displacement ellipsoids for the non-H atoms are drawn at the 50% probability level. Hydrogen bonds are shown as dashed lines.
Fig. 2.
Part of the packing of (I) viewed along the direction [010]. Hydrogen bonds are shown as dashed lines. H atoms not involved in hydrogen bonds have been omitted for clarity.

Crystal data

C5H7N2+·C10H6IO4S·2H2OF000 = 952
Mr = 480.27Dx = 1.799 Mg m3
Monoclinic, P21/nMo Kα radiation λ = 0.71073 Å
Hall symbol: -P 2ynCell parameters from 9093 reflections
a = 15.0219 (6) Åθ = 2.4–27.7º
b = 6.9917 (3) ŵ = 1.96 mm1
c = 18.0729 (7) ÅT = 296 (2) K
β = 110.868 (1)ºBlock, yellow
V = 1773.66 (12) Å30.18 × 0.12 × 0.10 mm
Z = 4

Data collection

Bruker SMART APEX CCD diffractometer3484 independent reflections
Radiation source: fine-focus sealed tube3128 reflections with I > 2σ(I)
Monochromator: graphiteRint = 0.027
T = 296(2) Kθmax = 26.0º
ω scansθmin = 2.2º
Absorption correction: multi-scan(SADABS; Bruker, 2001)h = −18→18
Tmin = 0.720, Tmax = 0.828k = −8→8
17926 measured reflectionsl = −22→22

Refinement

Refinement on F2Secondary atom site location: difference Fourier map
Least-squares matrix: fullHydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.025H atoms treated by a mixture of independent and constrained refinement
wR(F2) = 0.069  w = 1/[σ2(Fo2) + (0.0364P)2 + 1.4355P] where P = (Fo2 + 2Fc2)/3
S = 1.08(Δ/σ)max < 0.001
3484 reflectionsΔρmax = 0.71 e Å3
258 parametersΔρmin = −0.96 e Å3
34 restraintsExtinction correction: none
Primary atom site location: structure-invariant direct methods

Special details

Geometry. All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell e.s.d.'s are taken into account individually in the estimation of e.s.d.'s in distances, angles and torsion angles; correlations between e.s.d.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell e.s.d.'s is used for estimating e.s.d.'s involving l.s. planes.
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)

xyzUiso*/Ueq
N10.7208 (2)0.1965 (4)−0.01736 (18)0.0486 (7)
H1A0.6708 (18)0.233 (5)−0.0582 (16)0.056 (11)*
N20.7670 (2)0.0577 (5)0.18478 (18)0.0614 (8)
H2B0.7069 (11)0.034 (6)0.179 (2)0.065 (11)*
H2C0.8150 (18)0.008 (5)0.2246 (15)0.059 (10)*
C110.8061 (3)0.1948 (5)−0.0234 (2)0.0564 (9)
H11A0.81350.2277−0.07080.068*
C120.8834 (2)0.1434 (5)0.0416 (2)0.0577 (9)
H12A0.94380.14050.03840.069*
C130.8718 (2)0.0965 (5)0.1112 (2)0.0541 (8)
H13A0.92450.06180.15500.065*
C140.7811 (2)0.1006 (4)0.11680 (19)0.0433 (7)
C150.7058 (2)0.1516 (4)0.0493 (2)0.0447 (7)
H15A0.64430.15470.05020.054*
S10.51967 (4)0.21097 (9)0.19020 (4)0.03081 (15)
I10.159514 (12)0.20253 (3)0.230170 (10)0.03822 (8)
O10.54976 (13)0.0659 (3)0.14622 (13)0.0469 (5)
O20.55842 (13)0.3982 (3)0.18257 (13)0.0469 (5)
O30.53822 (15)0.1580 (4)0.27109 (13)0.0570 (6)
O40.10004 (13)0.2998 (3)0.04865 (12)0.0393 (5)
H40.080 (3)0.315 (6)−0.0008 (7)0.071 (13)*
C10.39401 (17)0.2327 (4)0.14385 (15)0.0273 (5)
C20.33925 (18)0.2092 (3)0.18943 (15)0.0285 (5)
H2A0.36820.17840.24270.034*
C30.24002 (18)0.2308 (4)0.15712 (15)0.0281 (5)
C40.19533 (17)0.2770 (3)0.07873 (15)0.0275 (5)
C50.25099 (18)0.3043 (3)0.03008 (15)0.0275 (5)
C60.20225 (16)0.3533 (3)−0.04661 (13)0.0230 (5)
H60.13640.3671−0.06550.028*
C70.2508 (2)0.3803 (4)−0.09292 (16)0.0399 (6)
H70.21790.4140−0.14540.048*
C80.3502 (2)0.3611 (5)−0.06744 (17)0.0423 (7)
H80.38180.3819−0.10270.051*
C90.4003 (2)0.3120 (4)0.00897 (17)0.0371 (6)
H90.46610.29850.02620.045*
C100.35128 (18)0.2815 (3)0.06225 (15)0.0275 (5)
O1W−0.02157 (17)0.3572 (4)−0.09765 (13)0.0532 (6)
H1WA−0.038 (2)0.473 (2)−0.095 (2)0.060 (5)*
H1WB0.002 (2)0.359 (4)−0.1337 (16)0.056 (5)*
O2W0.55451 (16)0.2736 (3)−0.13855 (17)0.0555 (6)
H2WA0.5162 (18)0.179 (3)−0.147 (2)0.059 (11)*
H2WB0.5167 (18)0.370 (3)−0.151 (2)0.072 (13)*

Atomic displacement parameters (Å2)

U11U22U33U12U13U23
N10.0482 (16)0.0385 (14)0.0518 (16)−0.0003 (12)0.0091 (13)0.0011 (12)
N20.0386 (16)0.090 (2)0.0548 (17)0.0127 (16)0.0150 (14)0.0124 (16)
C110.063 (2)0.0483 (19)0.064 (2)−0.0091 (16)0.0302 (19)0.0008 (16)
C120.0395 (17)0.060 (2)0.080 (3)−0.0068 (15)0.0282 (18)0.0007 (19)
C130.0307 (15)0.058 (2)0.068 (2)0.0012 (14)0.0112 (15)0.0044 (17)
C140.0321 (14)0.0431 (16)0.0531 (17)0.0027 (12)0.0129 (13)−0.0010 (14)
C150.0316 (14)0.0430 (16)0.0580 (19)0.0040 (12)0.0142 (14)0.0016 (14)
S10.0198 (3)0.0380 (3)0.0329 (3)0.0003 (2)0.0073 (2)0.0048 (3)
I10.03151 (12)0.05175 (14)0.03694 (12)0.00166 (7)0.01898 (8)0.00622 (8)
O10.0299 (10)0.0489 (12)0.0630 (13)0.0051 (9)0.0180 (9)−0.0058 (10)
O20.0289 (10)0.0424 (11)0.0616 (13)−0.0083 (9)0.0066 (9)0.0054 (10)
O30.0303 (11)0.0986 (19)0.0378 (11)0.0063 (11)0.0069 (9)0.0226 (12)
O40.0214 (9)0.0645 (14)0.0313 (11)0.0048 (8)0.0084 (8)0.0037 (9)
C10.0206 (11)0.0297 (12)0.0318 (13)0.0004 (9)0.0095 (10)0.0015 (10)
C20.0258 (12)0.0323 (13)0.0261 (12)0.0011 (10)0.0078 (10)0.0036 (10)
C30.0249 (12)0.0336 (13)0.0297 (12)−0.0003 (10)0.0144 (10)0.0007 (10)
C40.0214 (12)0.0318 (12)0.0297 (12)0.0013 (10)0.0095 (10)−0.0014 (10)
C50.0255 (12)0.0278 (12)0.0296 (12)−0.0006 (9)0.0101 (10)−0.0019 (9)
C60.0162 (10)0.0326 (12)0.0178 (10)0.0005 (9)0.0030 (8)0.0016 (9)
C70.0390 (15)0.0479 (16)0.0289 (13)−0.0033 (13)0.0075 (11)0.0030 (12)
C80.0375 (15)0.0600 (18)0.0342 (14)−0.0037 (14)0.0188 (12)0.0049 (13)
C90.0274 (13)0.0495 (16)0.0362 (14)−0.0016 (12)0.0135 (12)0.0028 (12)
C100.0248 (12)0.0285 (12)0.0288 (12)−0.0015 (9)0.0092 (10)−0.0006 (10)
O1W0.0462 (12)0.0741 (16)0.0393 (12)0.0129 (12)0.0151 (10)0.0012 (11)
O2W0.0377 (12)0.0424 (13)0.0792 (18)0.0006 (10)0.0122 (12)−0.0025 (12)

Geometric parameters (Å, °)

N1—C111.325 (5)C1—C21.366 (4)
N1—C151.339 (4)C1—C101.424 (4)
N1—H1A0.882 (10)C2—C31.402 (4)
N2—C141.353 (4)C2—H2A0.9300
N2—H2B0.886 (10)C3—C41.373 (4)
N2—H2C0.888 (10)C4—C51.425 (4)
C11—C121.374 (5)C5—C61.361 (3)
C11—H11A0.9300C5—C101.417 (4)
C12—C131.369 (5)C6—C71.305 (4)
C12—H12A0.9300C6—H60.9300
C13—C141.403 (4)C7—C81.404 (4)
C13—H13A0.9300C7—H70.9300
C14—C151.382 (4)C8—C91.360 (4)
C15—H15A0.9300C8—H80.9300
S1—O31.436 (2)C9—C101.421 (4)
S1—O11.456 (2)C9—H90.9300
S1—O21.459 (2)O1W—H1WA0.851 (10)
S1—C11.778 (2)O1W—H1WB0.847 (10)
I1—C32.093 (2)O2W—H2WA0.853 (10)
O4—C41.347 (3)O2W—H2WB0.856 (10)
O4—H40.843 (10)
C11—N1—C15123.4 (3)C10—C1—S1121.29 (19)
C11—N1—H1A120 (3)C1—C2—C3121.0 (2)
C15—N1—H1A117 (3)C1—C2—H2A119.5
C14—N2—H2B115 (2)C3—C2—H2A119.5
C14—N2—H2C119 (2)C4—C3—C2120.8 (2)
H2B—N2—H2C122 (4)C4—C3—I1119.55 (18)
N1—C11—C12118.6 (4)C2—C3—I1119.64 (19)
N1—C11—H11A120.7O4—C4—C3120.2 (2)
C12—C11—H11A120.7O4—C4—C5120.5 (2)
C13—C12—C11120.3 (3)C3—C4—C5119.3 (2)
C13—C12—H12A119.9C6—C5—C10123.6 (2)
C11—C12—H12A119.9C6—C5—C4116.2 (2)
C12—C13—C14120.4 (3)C10—C5—C4120.2 (2)
C12—C13—H13A119.8C7—C6—C5118.0 (2)
C14—C13—H13A119.8C7—C6—H6121.0
N2—C14—C15121.0 (3)C5—C6—H6121.0
N2—C14—C13122.1 (3)C6—C7—C8123.2 (3)
C15—C14—C13116.9 (3)C6—C7—H7118.4
N1—C15—C14120.5 (3)C8—C7—H7118.4
N1—C15—H15A119.8C9—C8—C7119.7 (3)
C14—C15—H15A119.8C9—C8—H8120.1
O3—S1—O1113.00 (15)C7—C8—H8120.1
O3—S1—O2112.85 (15)C8—C9—C10119.6 (3)
O1—S1—O2111.19 (13)C8—C9—H9120.2
O3—S1—C1106.86 (12)C10—C9—H9120.2
O1—S1—C1106.64 (12)C5—C10—C9115.9 (2)
O2—S1—C1105.73 (12)C5—C10—C1118.2 (2)
C4—O4—H4111 (3)C9—C10—C1125.9 (2)
C2—C1—C10120.5 (2)H1WA—O1W—H1WB103.8 (15)
C2—C1—S1118.17 (19)H2WA—O2W—H2WB102.6 (15)

Hydrogen-bond geometry (Å, °)

D—H···AD—HH···AD···AD—H···A
N1—H1A···O2W0.882 (10)1.853 (13)2.725 (4)170 (4)
N2—H2B···O10.886 (10)2.232 (16)3.085 (3)162 (4)
N2—H2C···O2i0.888 (10)2.179 (11)3.064 (4)175 (3)
O4—H4···O1W0.843 (10)1.89 (2)2.655 (3)150 (4)
O1W—H1WB···O3ii0.847 (10)1.983 (12)2.822 (3)171 (4)
O1W—H1WA···O4iii0.851 (10)2.158 (15)2.944 (3)153 (3)
O2W—H2WA···O1iv0.853 (10)1.981 (12)2.820 (3)167 (3)
O2W—H2WB···O2v0.856 (10)1.944 (11)2.796 (3)173 (3)

Symmetry codes: (i) −x+3/2, y−1/2, −z+1/2; (ii) x−1/2, −y+1/2, z−1/2; (iii) −x, −y+1, −z; (iv) −x+1, −y, −z; (v) −x+1, −y+1, −z.

Footnotes

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: HB2719).

References

  • Bruker (2001). SADABS, SAINT-Plus and SMART Bruker AXS, Inc., Madison, Wisconsin, USA.
  • Li, J. (2007). Acta Cryst. E63, o4171.
  • Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. [PubMed]
  • Spek, A. L. (2003). J. Appl. Cryst.36, 7–13.

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