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Acta Crystallogr Sect E Struct Rep Online. 2009 October 1; 65(Pt 10): m1183.
Published online 2009 September 9. doi:  10.1107/S1600536809034473
PMCID: PMC2970308

Diaqua­bis[3-(2-sulfanylphen­yl)prop-2-enoato]zinc(II) dihydrate

Abstract

In the title compound, [Zn(C9H7O2S)2(H2O)2]·2H2O, the ZnII atom (site symmetry An external file that holds a picture, illustration, etc.
Object name is e-65-m1183-efi1.jpg) is four-coordinated by two O atoms from 3-(2-sulfanylphen­yl)prop-2-enoate anions and two aqua O atoms in a slightly distorted ZnO4 square-planar arrangement. In the crystal, O—H(...)O hydrogen bonds help to establish the packing.

Related literature

For background to coordination networks, see: Cheng et al., (2006 [triangle]). For reference structural data, see: Allen et al. (1987 [triangle]).

An external file that holds a picture, illustration, etc.
Object name is e-65-m1183-scheme1.jpg

Experimental

Crystal data

  • [Zn(C9H7O2S)2(H2O)2]·2H2O
  • M r = 495.85
  • Monoclinic, An external file that holds a picture, illustration, etc.
Object name is e-65-m1183-efi2.jpg
  • a = 18.4398 (5) Å
  • b = 7.7188 (3) Å
  • c = 7.3258 (2) Å
  • β = 98.578 (2)°
  • V = 1031.04 (6) Å3
  • Z = 2
  • Mo Kα radiation
  • μ = 1.44 mm−1
  • T = 298 K
  • 0.30 × 0.20 × 0.14 mm

Data collection

  • Enraf–Nonius CAD-4 diffractometer
  • Absorption correction: ψ scan (North et al., 1968 [triangle]) T min = 0.673, T max = 0.824
  • 6272 measured reflections
  • 1811 independent reflections
  • 1441 reflections with I > 2σ(I)
  • R int = 0.092
  • 200 standard reflections every 3 reflections intensity decay: 1%

Refinement

  • R[F 2 > 2σ(F 2)] = 0.067
  • wR(F 2) = 0.185
  • S = 1.06
  • 1811 reflections
  • 146 parameters
  • 6 restraints
  • H atoms treated by a mixture of independent and constrained refinement
  • Δρmax = 0.93 e Å−3
  • Δρmin = −0.88 e Å−3

Data collection: CAD-4 Software (Enraf–Nonius, 1989 [triangle]); cell refinement: CAD-4 Software; data reduction: XCAD4 (Harms & Wocadlo, 1995 [triangle]); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 [triangle]); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 [triangle]); molecular graphics: SHELXTL (Sheldrick, 2008 [triangle]); software used to prepare material for publication: SHELXTL.

Table 1
Selected bond lengths (Å)
Table 2
Hydrogen-bond geometry (Å, °)

Supplementary Material

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536809034473/hb5073sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809034473/hb5073Isup2.hkl

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

Acknowledgments

The project was supported by the Scientific Research Foundation for Returned Overseas Chinese Scholars, State Education Ministry, Educational Commission of Hubei Province (D20091703) and the Natural Science Foundation of Hubei Province (2008CDB038).

supplementary crystallographic information

Comment

There has been much research interest in acid metal complexes due to their molecular architectures and biological activities (e.g. Cheng et al., 2006). In this work, we report here the crystal structure of the title compound, (I). In (I), all bond lengths are within normal ranges (Allen et al., 1987) (Fig. 1). The ZnII atom is four-coordinated by two O atoms from the 3-(2-sulfanylphenyl)propanoate and two O atoms from the water molecules, forming a slightly distorted square-planar coordination.

Experimental

A mixture of 3-(2-sulfanylphenyl)propanoic acid (364 mg, 2 mmol) and ZnCl2 (1 mmol, 134 mg) in methanol (10 ml) was stirred for 3 h. After keeping the filtrate in air for 7 d, colourless blocks of (I) were formed.

Refinement

The water H atoms were located in a difference map and their positions were refined with restraints of O—H = 0.82 (1)Å. The other H atoms were positioned geometrically (C—H = 0.93Å, S—H = 1.20 Å) and refined as riding, with Uiso(H) = 1.2Ueq(carrier).

Figures

Fig. 1.
The molecular structure of (I) showing 30% probability displacement ellipsoids. Atoms with the suffix A are generated by the symmetry operation (2–x, 1–y, 1–z).

Crystal data

[Zn(C9H7O2S)2(H2O)2]·2H2OF(000) = 512
Mr = 495.85Dx = 1.597 Mg m3
Monoclinic, P21/cMo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybcCell parameters from 25 reflections
a = 18.4398 (5) Åθ = 9–12°
b = 7.7188 (3) ŵ = 1.44 mm1
c = 7.3258 (2) ÅT = 298 K
β = 98.578 (2)°Block, colourless
V = 1031.04 (6) Å30.30 × 0.20 × 0.14 mm
Z = 2

Data collection

Enraf–Nonius CAD-4 diffractometer1441 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tubeRint = 0.092
graphiteθmax = 25.0°, θmin = 2.2°
ω/2θ scansh = −21→18
Absorption correction: ψ scan (North et al., 1968)k = −9→8
Tmin = 0.673, Tmax = 0.824l = −8→8
6272 measured reflections200 standard reflections every 3 reflections
1811 independent reflections intensity decay: 1%

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)] = 0.067Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.185H atoms treated by a mixture of independent and constrained refinement
S = 1.06w = 1/[σ2(Fo2) + (0.1071P)2 + 0.9875P] where P = (Fo2 + 2Fc2)/3
1811 reflections(Δ/σ)max = 0.001
146 parametersΔρmax = 0.93 e Å3
6 restraintsΔρmin = −0.88 e Å3

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
C10.6975 (3)0.9228 (8)0.6126 (7)0.0401 (13)
C20.6254 (3)0.8922 (8)0.6435 (8)0.0442 (14)
C30.5803 (4)1.0275 (10)0.6681 (10)0.0590 (19)
H30.53271.00420.68920.071*
C40.6020 (4)1.1926 (10)0.6630 (11)0.070 (2)
H40.57001.28180.68110.084*
C50.6739 (4)1.2307 (10)0.6300 (10)0.066 (2)
H50.68981.34460.62530.079*
C60.7196 (3)1.0945 (8)0.6051 (9)0.0500 (16)
H60.76691.11830.58250.060*
C70.7479 (3)0.7796 (7)0.5892 (7)0.0374 (12)
H70.73260.66850.61500.045*
C80.8132 (3)0.7942 (7)0.5345 (7)0.0361 (12)
H80.82810.90300.50030.043*
C90.8630 (3)0.6463 (7)0.5254 (7)0.0354 (12)
H3A1.0261 (19)0.464 (7)0.180 (6)0.043*
H4A0.866 (2)0.294 (4)0.419 (8)0.043*
H3B0.964 (2)0.558 (6)0.165 (6)0.043*
H4B0.861 (2)0.133 (5)0.346 (8)0.043*
O10.92576 (19)0.6850 (5)0.4821 (5)0.0401 (9)
O20.8441 (3)0.4964 (5)0.5594 (7)0.0530 (12)
O30.9908 (3)0.4908 (6)0.2311 (6)0.0499 (11)
O40.8892 (3)0.2064 (6)0.3989 (8)0.0666 (13)
S10.59232 (9)0.6819 (2)0.6468 (3)0.0601 (6)
H10.59700.61260.50240.090*
Zn11.00000.50000.50000.0327 (4)

Atomic displacement parameters (Å2)

U11U22U33U12U13U23
C10.038 (3)0.044 (3)0.039 (3)0.008 (3)0.008 (2)−0.006 (3)
C20.040 (3)0.050 (4)0.045 (3)0.005 (3)0.013 (3)0.001 (3)
C30.040 (4)0.071 (5)0.069 (5)0.018 (3)0.018 (3)0.003 (4)
C40.063 (5)0.062 (5)0.088 (5)0.033 (4)0.020 (4)−0.004 (4)
C50.078 (5)0.042 (4)0.079 (5)0.013 (4)0.021 (4)−0.012 (3)
C60.040 (3)0.041 (4)0.072 (4)0.005 (3)0.017 (3)−0.004 (3)
C70.034 (3)0.034 (3)0.045 (3)0.005 (2)0.008 (2)0.002 (2)
C80.037 (3)0.032 (3)0.040 (3)0.005 (2)0.011 (2)0.003 (2)
C90.037 (3)0.038 (3)0.032 (3)0.007 (2)0.009 (2)−0.002 (2)
O10.032 (2)0.045 (2)0.045 (2)0.0091 (16)0.0099 (17)0.0037 (17)
O20.052 (3)0.035 (3)0.075 (3)0.0035 (19)0.019 (2)0.000 (2)
O30.062 (3)0.052 (3)0.040 (2)0.017 (2)0.021 (2)0.0060 (18)
O40.074 (3)0.049 (3)0.082 (4)0.014 (2)0.030 (3)−0.004 (3)
S10.0465 (9)0.0555 (11)0.0842 (13)−0.0072 (8)0.0287 (9)0.0035 (9)
Zn10.0348 (6)0.0360 (6)0.0300 (5)0.0075 (4)0.0139 (4)0.0046 (3)

Geometric parameters (Å, °)

C1—C61.390 (10)C8—C91.473 (7)
C1—C21.402 (8)C8—H80.9300
C1—C71.470 (8)C9—O21.245 (6)
C2—C31.364 (9)C9—O11.280 (6)
C2—S11.735 (7)Zn1—O11.969 (4)
C3—C41.338 (10)Zn1—O31.953 (4)
C3—H30.9300O3—H3A0.824 (10)
C4—C51.413 (11)O3—H3B0.823 (10)
C4—H40.9300O4—H4A0.821 (10)
C5—C61.376 (9)O4—H4B0.819 (10)
C5—H50.9300S1—H11.2000
C6—H60.9300Zn1—O3i1.953 (4)
C7—C81.330 (7)Zn1—O1i1.969 (4)
C7—H70.9300
C6—C1—C2117.2 (5)C1—C7—H7117.0
C6—C1—C7121.3 (5)C7—C8—C9123.2 (5)
C2—C1—C7121.5 (6)C7—C8—H8118.4
C3—C2—C1120.3 (6)C9—C8—H8118.4
C3—C2—S1119.4 (5)O2—C9—O1123.9 (5)
C1—C2—S1120.3 (5)O2—C9—C8121.0 (5)
C4—C3—C2122.3 (7)O1—C9—C8115.0 (5)
C4—C3—H3118.9C9—O1—Zn1117.3 (4)
C2—C3—H3118.9Zn1—O3—H3A121 (4)
C3—C4—C5119.7 (6)Zn1—O3—H3B121 (4)
C3—C4—H4120.1H3A—O3—H3B110.2 (18)
C5—C4—H4120.1H4A—O4—H4B110.3 (18)
C6—C5—C4118.2 (7)C2—S1—H1109.5
C6—C5—H5120.9O3i—Zn1—O3180.0
C4—C5—H5120.9O3i—Zn1—O1i90.25 (17)
C5—C6—C1122.3 (6)O3—Zn1—O1i89.75 (17)
C5—C6—H6118.8O3i—Zn1—O189.75 (17)
C1—C6—H6118.8O3—Zn1—O190.25 (17)
C8—C7—C1126.0 (5)O1i—Zn1—O1180.0
C8—C7—H7117.0
C6—C1—C2—C3−1.1 (9)C7—C1—C6—C5−178.8 (6)
C7—C1—C2—C3178.8 (6)C6—C1—C7—C8−10.0 (9)
C6—C1—C2—S1177.7 (4)C2—C1—C7—C8170.1 (6)
C7—C1—C2—S1−2.4 (8)C1—C7—C8—C9175.9 (5)
C1—C2—C3—C40.4 (11)C7—C8—C9—O24.1 (8)
S1—C2—C3—C4−178.5 (6)C7—C8—C9—O1−175.4 (5)
C2—C3—C4—C50.4 (12)O2—C9—O1—Zn1−7.6 (7)
C3—C4—C5—C6−0.4 (11)C8—C9—O1—Zn1171.9 (3)
C4—C5—C6—C1−0.4 (10)C9—O1—Zn1—O3i−70.7 (4)
C2—C1—C6—C51.2 (9)C9—O1—Zn1—O3109.3 (4)

Symmetry codes: (i) −x+2, −y+1, −z+1.

Hydrogen-bond geometry (Å, °)

D—H···AD—HH···AD···AD—H···A
O3—H3A···O4ii0.82 (4)2.56 (5)3.033 (7)118 (5)
O3—H3B···O1iii0.82 (4)2.44 (5)3.221 (6)159 (4)
O4—H4A···O20.83 (3)1.95 (4)2.716 (7)155 (5)
O4—H4B···O2iv0.83 (4)2.30 (6)2.951 (7)136 (4)

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

Footnotes

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: HB5073).

References

  • Allen, F. H., Kennard, O., Watson, D. G., Brammer, L., Orpen, A. G. & Taylor, R. (1987). J. Chem. Soc. Perkin Trans. 2, pp. S1–19.
  • Cheng, K., Zhu, H.-L. & Li, Y.-G. (2006). Z. Anorg. Allg. Chem.632, 2326–2330.
  • Enraf–Nonius (1989). CAD-4 Software Enraf–Nonius, Delft, The Netherlands.
  • Harms, K. & Wocadlo, S. (1995). XCAD4 University of Marburg, Germany.
  • North, A. C. T., Phillips, D. C. & Mathews, F. S. (1968). Acta Cryst. A24, 351–359.
  • Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. [PubMed]

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