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Acta Cryst. (2009). E65, m1493    [ doi:10.1107/S1600536809044948 ]

Diaquabis(4-oxo-1,4-dihydropyridine-3-sulfonato-[kappa]2O3,O4)zinc(II)

Z.-B. Zhu, S. Gao and S. W. Ng

Abstract top

In the crystal structure of the title compound, [Zn(C5H4NO4S)2(H2O)2], the 4-oxo-1,4-dihydropyridine-3-sulfonate anion chelates to water-coordinated zinc centres through the carbonyl O atom and through one O atom of the sulfonate group. The ZnII atom lies on a center of inversion, and adjacent molecules are linked by N-H...O and O-H...O hydrogen bonds, forming a three-dimensional network.

Related literature top

For the structure of the 4-oxo-1,4-dihydropyridine-3-sulfonate anion, see: Zhu et al. (2009).

Experimental top

Zinc carbonate (0.25 g, 2 mmol) was added to a hot aqueous solution of 4-hydroxypyridine-3-sulfonic acid (0.35 g, 2 mmol); the pH value was adjusted to6 with 0.1 M sodium hydroxide. The solution was allowed to evaporate slowly at room temperature, and colorless prismatic crystals were isolated after about five days. CH&N elemental analysis. Calc. for C10H12N2O10S2Zn:C 26.71, H 2.69, N 6.23%; found: C 26.73, H 2.73, N 6.21%.

Refinement top

Carbon-bound H-atoms were placed in calculated positions (C—H 0.93 Å) and were included in the refinement in the riding model approximation, with U(H) set to 1.2U(C). The amino and water H-atoms were located in a difference Fourier map, and were refined isotropically with a distance restraint of N–H = O–H = 0.85±0.01 Å.

Computing details top

Data collection: RAPID-AUTO (Rigaku, 1998); cell refinement: RAPID-AUTO (Rigaku, 1998); data reduction: CrystalClear (Rigaku/MSC, 2002); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: X-SEED (Barbour, 2001); software used to prepare material for publication: publCIF (Westrip, 2009).

Figures top
[Figure 1] Fig. 1. Anisotropic displacement ellipsoid plot (Barbour, 2001) of Zn(H2O)2(C5H4NO4S)2 at the 50% probability level; hydrogen atoms are drawn as spheres of arbitrary radius.
Diaquabis(4-oxo-1,4-dihydropyridine-3-sulfonato- κ2O3,O4)zinc(II) top
Crystal data top
[Zn(C5H4NO4S)2(H2O)2]F(000) = 456
Mr = 449.71Dx = 1.968 Mg m−3
Monoclinic, P21/cMo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybcCell parameters from 6865 reflections
a = 4.9263 (1) Åθ = 3.4–27.5°
b = 20.9529 (6) ŵ = 1.95 mm−1
c = 7.4437 (2) ÅT = 293 K
β = 98.9371 (9)°Prism, colorless
V = 759.01 (3) Å30.23 × 0.17 × 0.14 mm
Z = 2
Data collection top
Rigaku R-AXIS RAPID IP
diffractometer		1738 independent reflections
Radiation source: fine-focus sealed tube1629 reflections with I > 2σ(I)
graphiteRint = 0.021
ω scansθmax = 27.5°, θmin = 3.4°
Absorption correction: multi-scan
(ABSCOR; Higashi, 1995)		h = −6→5
Tmin = 0.662, Tmax = 0.772k = −27→27
7334 measured reflectionsl = −9→9
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)] = 0.025Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.074H atoms treated by a mixture of independent and constrained refinement
S = 1.10 w = 1/[σ2(Fo2) + (0.0399P)2 + 0.5207P]
where P = (Fo2 + 2Fc2)/3
1738 reflections(Δ/σ)max = 0.001
127 parametersΔρmax = 0.45 e Å−3
3 restraintsΔρmin = −0.45 e Å−3
Crystal data top
[Zn(C5H4NO4S)2(H2O)2]V = 759.01 (3) Å3
Mr = 449.71Z = 2
Monoclinic, P21/cMo Kα radiation
a = 4.9263 (1) ŵ = 1.95 mm−1
b = 20.9529 (6) ÅT = 293 K
c = 7.4437 (2) Å0.23 × 0.17 × 0.14 mm
β = 98.9371 (9)°
Data collection top
Rigaku R-AXIS RAPID IP
diffractometer		1738 independent reflections
Absorption correction: multi-scan
(ABSCOR; Higashi, 1995)		1629 reflections with I > 2σ(I)
Tmin = 0.662, Tmax = 0.772Rint = 0.021
7334 measured reflectionsθmax = 27.5°
Refinement top
R[F2 > 2σ(F2)] = 0.025H atoms treated by a mixture of independent and constrained refinement
wR(F2) = 0.074Δρmax = 0.45 e Å−3
S = 1.10Δρmin = −0.45 e Å−3
1738 reflectionsAbsolute structure: ?
127 parametersFlack parameter: ?
3 restraintsRogers parameter: ?
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
Zn10.50000.50000.50000.01991 (11)
S10.54548 (9)0.35166 (2)0.43742 (6)0.02251 (13)
O10.6943 (3)0.41242 (6)0.46588 (19)0.0246 (3)
O20.4026 (3)0.33653 (7)0.5890 (2)0.0327 (3)
O30.7182 (3)0.30080 (7)0.3867 (2)0.0380 (4)
O40.1877 (3)0.47222 (6)0.29786 (18)0.0238 (3)
O1W0.7120 (3)0.54012 (7)0.3004 (2)0.0279 (3)
N1−0.0061 (4)0.30854 (10)0.0136 (2)0.0361 (5)
C10.2078 (4)0.30795 (10)0.1490 (3)0.0303 (4)
H1A0.30530.27030.17640.036*
C20.2849 (4)0.36189 (8)0.2474 (3)0.0221 (4)
C30.1359 (4)0.42039 (8)0.2098 (2)0.0209 (4)
C4−0.0876 (4)0.41740 (10)0.0613 (3)0.0294 (4)
H4−0.18970.45400.02740.035*
C5−0.1522 (5)0.36232 (11)−0.0300 (3)0.0353 (5)
H5A−0.29980.3615−0.12450.042*
H10.738 (5)0.5794 (5)0.318 (4)0.035 (7)*
H20.866 (3)0.5233 (13)0.301 (4)0.040 (7)*
H3−0.081 (6)0.2742 (9)−0.028 (4)0.051 (8)*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Zn10.01975 (17)0.01417 (16)0.02420 (18)−0.00106 (10)−0.00165 (12)−0.00169 (10)
S10.0258 (2)0.0128 (2)0.0270 (2)0.00172 (16)−0.00212 (18)0.00056 (16)
O10.0221 (6)0.0168 (6)0.0333 (7)0.0005 (5)−0.0006 (5)−0.0015 (5)
O20.0433 (8)0.0247 (7)0.0286 (7)−0.0061 (6)0.0009 (6)0.0042 (6)
O30.0398 (8)0.0203 (7)0.0503 (10)0.0124 (6)−0.0037 (7)−0.0046 (6)
O40.0226 (6)0.0168 (6)0.0295 (7)0.0010 (5)−0.0042 (5)−0.0031 (5)
O1W0.0263 (7)0.0244 (7)0.0333 (8)0.0020 (6)0.0059 (6)0.0008 (6)
N10.0443 (11)0.0297 (10)0.0324 (10)−0.0131 (8)0.0006 (8)−0.0141 (7)
C10.0366 (11)0.0203 (9)0.0337 (10)−0.0038 (8)0.0046 (8)−0.0065 (8)
C20.0253 (9)0.0178 (8)0.0224 (9)−0.0022 (7)0.0008 (7)−0.0024 (6)
C30.0215 (8)0.0189 (8)0.0212 (8)−0.0032 (7)−0.0005 (7)0.0008 (6)
C40.0300 (10)0.0295 (10)0.0256 (9)−0.0034 (8)−0.0061 (8)0.0025 (8)
C50.0364 (11)0.0414 (12)0.0248 (10)−0.0108 (9)−0.0056 (8)−0.0042 (8)
Geometric parameters (Å, °) top
Zn1—O42.0618 (12)O1W—H20.835 (10)
Zn1—O4i2.0618 (12)N1—C11.340 (3)
Zn1—O1i2.1031 (13)N1—C51.349 (3)
Zn1—O12.1031 (13)N1—H30.846 (10)
Zn1—O1Wi2.1183 (15)C1—C21.368 (3)
Zn1—O1W2.1183 (15)C1—H1A0.9300
S1—O31.4496 (15)C2—C31.434 (2)
S1—O21.4547 (17)C3—C41.435 (2)
S1—O11.4681 (13)C4—C51.352 (3)
S1—C21.7694 (19)C4—H40.9300
O4—C31.274 (2)C5—H5A0.9300
O1W—H10.841 (10)
O4—Zn1—O4i180.00 (7)C3—O4—Zn1133.12 (12)
O4—Zn1—O1i91.86 (5)Zn1—O1W—H1111.3 (18)
O4i—Zn1—O1i88.14 (5)Zn1—O1W—H2112 (2)
O4—Zn1—O188.14 (5)H1—O1W—H2107 (3)
O4i—Zn1—O191.86 (5)C1—N1—C5121.09 (18)
O1i—Zn1—O1180.0C1—N1—H3121 (2)
O4—Zn1—O1Wi90.38 (6)C5—N1—H3116 (2)
O4i—Zn1—O1Wi89.62 (6)N1—C1—C2121.0 (2)
O1i—Zn1—O1Wi88.76 (5)N1—C1—H1A119.5
O1—Zn1—O1Wi91.24 (5)C2—C1—H1A119.5
O4—Zn1—O1W89.62 (6)C1—C2—C3120.70 (17)
O4i—Zn1—O1W90.38 (6)C1—C2—S1115.75 (15)
O1i—Zn1—O1W91.24 (5)C3—C2—S1123.06 (13)
O1—Zn1—O1W88.76 (5)O4—C3—C2124.95 (16)
O1Wi—Zn1—O1W180.00 (7)O4—C3—C4120.14 (17)
O3—S1—O2114.58 (10)C2—C3—C4114.91 (16)
O3—S1—O1112.02 (9)C5—C4—C3121.1 (2)
O2—S1—O1111.59 (9)C5—C4—H4119.4
O3—S1—C2105.27 (9)C3—C4—H4119.4
O2—S1—C2105.55 (9)C4—C5—N1121.12 (18)
O1—S1—C2107.12 (8)C4—C5—H5A119.4
S1—O1—Zn1123.21 (8)N1—C5—H5A119.4
O3—S1—O1—Zn1170.03 (10)O2—S1—C2—C1−89.44 (17)
O2—S1—O1—Zn1−59.98 (12)O1—S1—C2—C1151.53 (16)
C2—S1—O1—Zn155.08 (12)O3—S1—C2—C3−155.77 (16)
O4—Zn1—O1—S1−40.93 (10)O2—S1—C2—C382.66 (17)
O4i—Zn1—O1—S1139.07 (10)O1—S1—C2—C3−36.38 (18)
O1Wi—Zn1—O1—S149.40 (10)Zn1—O4—C3—C26.9 (3)
O1W—Zn1—O1—S1−130.60 (10)Zn1—O4—C3—C4−173.69 (14)
O1i—Zn1—O4—C3−173.83 (17)C1—C2—C3—O4177.73 (19)
O1—Zn1—O4—C36.17 (17)S1—C2—C3—O46.0 (3)
O1Wi—Zn1—O4—C3−85.06 (18)C1—C2—C3—C4−1.7 (3)
O1W—Zn1—O4—C394.94 (18)S1—C2—C3—C4−173.44 (15)
C5—N1—C1—C20.0 (3)O4—C3—C4—C5−177.7 (2)
N1—C1—C2—C30.9 (3)C2—C3—C4—C51.8 (3)
N1—C1—C2—S1173.18 (17)C3—C4—C5—N1−1.0 (4)
O3—S1—C2—C132.14 (19)C1—N1—C5—C40.0 (3)
Symmetry codes: (i) −x+1, −y+1, −z+1.
Hydrogen-bond geometry (Å, °) top
D—H···AD—HH···AD···AD—H···A
O1w—H1···O2i0.84 (1)2.05 (2)2.797 (2)147 (2)
O1w—H2···O4ii0.84 (1)1.92 (1)2.744 (2)171 (3)
N1—H3···O3iii0.85 (1)1.91 (1)2.754 (2)175 (3)
Symmetry codes: (i) −x+1, −y+1, −z+1; (ii) x+1, y, z; (iii) x−1, −y+1/2, z−1/2.
Table 1
Hydrogen-bond geometry (Å, °) top
D—H···AD—HH···AD···AD—H···A
O1w—H1···O2i0.84 (1)2.05 (2)2.797 (2)147 (2)
O1w—H2···O4ii0.84 (1)1.92 (1)2.744 (2)171 (3)
N1—H3···O3iii0.85 (1)1.91 (1)2.754 (2)175 (3)
Symmetry codes: (i) −x+1, −y+1, −z+1; (ii) x+1, y, z; (iii) x−1, −y+1/2, z−1/2.
Acknowledgements top

We thank the Natural Science Foundation of Heilongjiang Province (No. B200501), Heilongjiang University and the University of Malaya for supporting this study.

references
References top

Barbour, L. J. (2001). J. Supramol. Chem. 1, 189–191.

Higashi, T. (1995). ABSCOR. Rigaku Corporation, Tokyo, Japan.

Rigaku (1998). RAPID-AUTO. Rigaku Corporation, Tokyo, Japan.

Rigaku/MSC (2002). CrystalClear. Rigaku/MSC Inc., The Woodlands, Texas, USA.

Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122.

Westrip, S. P. (2009). publCIF. In preparation.

Zhu, Z.-B., Gao, S. & Ng, S. W. (2009). Acta Cryst. E65, o2687.