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Acta Crystallogr Sect E Struct Rep Online. 2009 November 1; 65(Pt 11): m1493.
Published online 2009 October 31. doi:  10.1107/S1600536809044948
PMCID: PMC2971298

Diaqua­bis(4-oxo-1,4-dihydro­pyridine-3-sulfonato-κ2 O 3,O 4)zinc(II)

Abstract

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

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

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Object name is e-65-m1493-scheme1.jpg

Experimental

Crystal data

  • [Zn(C5H4NO4S)2(H2O)2]
  • M r = 449.71
  • Monoclinic, An external file that holds a picture, illustration, etc.
Object name is e-65-m1493-efi1.jpg
  • a = 4.9263 (1) Å
  • b = 20.9529 (6) Å
  • c = 7.4437 (2) Å
  • β = 98.9371 (9)°
  • V = 759.01 (3) Å3
  • Z = 2
  • Mo Kα radiation
  • μ = 1.95 mm−1
  • T = 293 K
  • 0.23 × 0.17 × 0.14 mm

Data collection

  • Rigaku R-AXIS RAPID IP diffractometer
  • Absorption correction: multi-scan (ABSCOR; Higashi, 1995 [triangle]) T min = 0.662, T max = 0.772
  • 7334 measured reflections
  • 1738 independent reflections
  • 1629 reflections with I > 2σ(I)
  • R int = 0.021

Refinement

  • R[F 2 > 2σ(F 2)] = 0.025
  • wR(F 2) = 0.074
  • S = 1.10
  • 1738 reflections
  • 127 parameters
  • 3 restraints
  • H atoms treated by a mixture of independent and constrained refinement
  • Δρmax = 0.45 e Å−3
  • Δρmin = −0.46 e Å−3

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

Table 1
Hydrogen-bond geometry (Å, °)

Supplementary Material

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536809044948/bt5120sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809044948/bt5120Isup2.hkl

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

Acknowledgments

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

supplementary crystallographic information

Experimental

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

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.

Figures

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.

Crystal data

[Zn(C5H4NO4S)2(H2O)2]F(000) = 456
Mr = 449.71Dx = 1.968 Mg m3
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 mm1
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

Rigaku R-AXIS RAPID IP diffractometer1738 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

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 = 1.10w = 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 Å3
3 restraintsΔρmin = −0.45 e Å3

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2)

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)

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, °)

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, °)

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.

Footnotes

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: BT5120).

References

  • 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. [PubMed]
  • Westrip, S. P. (2009). publCIF In preparation.
  • Zhu, Z.-B., Gao, S. & Ng, S. W. (2009). Acta Cryst. E65, o2687. [PMC free article] [PubMed]

Articles from Acta Crystallographica Section E: Structure Reports Online are provided here courtesy of International Union of Crystallography