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Acta Crystallogr Sect E Struct Rep Online. 2008 February 1; 64(Pt 2): m273.
Published online 2008 January 4. doi:  10.1107/S1600536807061703
PMCID: PMC2960324

Hexaaqua­zinc(II) bis­[4-(2-hydroxy­benzyl­ideneamino)benzene­sulfonate]

Abstract

In the title compound, [Zn(H2O)6](C13H10NO4S)2, a distorted ZnO6 octa­hedron results from the coordination by the six water mol­ecules. Only three of the water molecules are crystallographically unique, as the Zn atom lies on an inversion center. The Zn—O bond lengths are in the range 2.054 (4)–2.073 (4) Å. A network of hydrogen bonds helps to establish the crystal packing.

Related literature

For related literature, see: Tai et al. (2005 [triangle]).

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Object name is e-64-0m273-scheme1.jpg

Experimental

Crystal data

  • [Zn(H2O)6](C13H10NO4S)2
  • M r = 726.03
  • Monoclinic, An external file that holds a picture, illustration, etc.
Object name is e-64-0m273-efi1.jpg
  • a = 6.3255 (10) Å
  • b = 35.312 (3) Å
  • c = 6.9832 (10) Å
  • β = 90.391 (2)°
  • V = 1559.8 (4) Å3
  • Z = 2
  • Mo Kα radiation
  • μ = 0.99 mm−1
  • T = 298 (2) K
  • 0.35 × 0.33 × 0.20 mm

Data collection

  • Bruker SMART CCD area-detector diffractometer
  • Absorption correction: multi-scan (SADABS; Bruker, 1997 [triangle]) T min = 0.723, T max = 0.826
  • 6994 measured reflections
  • 2708 independent reflections
  • 2170 reflections with I > 2σ(I)
  • R int = 0.034

Refinement

  • R[F 2 > 2σ(F 2)] = 0.069
  • wR(F 2) = 0.168
  • S = 1.08
  • 2708 reflections
  • 205 parameters
  • H-atom parameters constrained
  • Δρmax = 0.37 e Å−3
  • Δρmin = −0.79 e Å−3

Data collection: SMART (Bruker, 1997 [triangle]); cell refinement: SAINT (Bruker, 1997 [triangle]); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997 [triangle]); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997 [triangle]); molecular graphics: SHELXTL (Bruker, 1997 [triangle]); software used to prepare material for publication: SHELXTL.

Table 1
Hydrogen-bond geometry (Å, °)

Supplementary Material

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536807061703/pr2013sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536807061703/pr2013Isup2.hkl

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

Acknowledgments

The authors thank the National Natural Science Foundation of China (20671073), NingXia Natural Gas Transferring Key Laboratory (2004007), the Science and Technology Foundation of Weifang and Weifang University for research grants.

supplementary crystallographic information

Comment

As part of our onging studies of metal coordination complexes with Shiff base ligands (Tai et al., 2005), the synthesis and structure of the title compound, (I), is reported. Six water molecules are attached to the zinc atom, resulting in a distorted ZnO6 octahedron (Fig. 1). The C7=N1 bond length [1.280 (9) Å] implies double bond character, while C4—O9 [1.332 (9) Å] is well regarded as a single bond. The dihedral angle between the two benzene ring mean planes (C1—C6 and C8—C13) is 32.2 (3)°. A network of hydrogen bonds helps to establish the crystal packing.

Experimental

One mmol of zinc acetate was added to a solution of salicylaldehyde-4-aminobenzene sulfonic acid (1 mmol) in 20 ml of 95% CH3CH2OH. The mixture was continuously stirred for 2 h at refluxing temperature, evaporating some methanol, then, upon cooling, the solid product was collected by filtration and dried in vacuo (yield 76%). Clear blocks of (I) were obtained by evaporation from a methanol solution after a week.

Refinement

The water H atoms were located in a difference map and refined as riding in their as-found relative positions with Uiso(H) = 1.2Ueq(O)". Other H atoms were placed geometrically (C—H = 0.93–0.97 Å, O—H = 0.82 Å, N—H = 0.86 Å) and refined as riding with Uiso(H) = 1.2Ueq(C,N) or 1.5Ueq(O).

Figures

Fig. 1.
The complex molecule in (I) with 50% probabiility ellipsoids (arbitrary spheres for the H atoms).

Crystal data

[Zn(H2O)6](C13H10NO4S)2F000 = 752
Mr = 726.03Dx = 1.546 Mg m3
Monoclinic, P21/nMo Kα radiation λ = 0.71073 Å
a = 6.3255 (10) ÅCell parameters from 2287 reflections
b = 35.312 (3) Åθ = 2.3–23.1º
c = 6.9832 (10) ŵ = 0.99 mm1
β = 90.391 (2)ºT = 298 (2) K
V = 1559.8 (4) Å3Block, colourless
Z = 20.35 × 0.33 × 0.20 mm

Data collection

Bruker SMART CCD area-detector diffractometer2708 independent reflections
Radiation source: fine-focus sealed tube2170 reflections with I > 2σ(I)
Monochromator: graphiteRint = 0.034
T = 298(2) Kθmax = 25.0º
phi and ω scansθmin = 2.3º
Absorption correction: multi-scan(SADABS; Bruker, 1997)h = −7→5
Tmin = 0.723, Tmax = 0.826k = −42→32
6994 measured reflectionsl = −8→8

Refinement

Refinement on F2Secondary atom site location: difference Fourier map
Least-squares matrix: fullHydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.069H-atom parameters constrained
wR(F2) = 0.168  w = 1/[σ2(Fo2) + (0.063P)2 + 5.0428P] where P = (Fo2 + 2Fc2)/3
S = 1.08(Δ/σ)max < 0.001
2708 reflectionsΔρmax = 0.37 e Å3
205 parametersΔρmin = −0.79 e Å3
Primary atom site location: structure-invariant direct methodsExtinction correction: none

Special details

Experimental. 'SADABS v2.0 (Bruker, 1997)'
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
Zn11.00000.00000.00000.0366 (3)
N10.4209 (9)0.23101 (16)0.5074 (8)0.0590 (15)
O10.8397 (6)0.06182 (11)0.5063 (6)0.0432 (10)
O20.5147 (6)0.05114 (12)0.6744 (6)0.0517 (11)
O30.5147 (6)0.05133 (12)0.3282 (6)0.0508 (11)
O40.1459 (9)0.28426 (15)0.5713 (9)0.0841 (17)
H40.17650.26350.52710.126*
O50.7091 (6)0.02586 (12)0.0024 (6)0.0508 (11)
H5A0.66330.0365−0.09890.061*
H5B0.64030.03520.09530.061*
O61.1063 (6)0.03918 (14)−0.1984 (7)0.0634 (13)
H6A1.23250.0438−0.23210.076*
H6B1.02730.0452−0.29260.076*
O71.1046 (6)0.03394 (15)0.2234 (6)0.0659 (14)
H7A1.02050.04280.30670.079*
H7B1.22850.03640.26960.079*
S10.6114 (2)0.06635 (4)0.5026 (2)0.0358 (4)
C10.5612 (8)0.11535 (16)0.4999 (7)0.0352 (12)
C20.7196 (10)0.14097 (18)0.5569 (9)0.0504 (16)
H20.85290.13230.59320.060*
C30.6734 (12)0.17949 (19)0.5582 (10)0.0616 (19)
H30.77700.19680.59460.074*
C40.4756 (11)0.19220 (18)0.5058 (10)0.0534 (16)
C50.3215 (11)0.16672 (18)0.4537 (10)0.0577 (18)
H50.18710.17550.42170.069*
C60.3630 (9)0.12829 (17)0.4482 (9)0.0486 (15)
H60.25840.11130.41000.058*
C70.5591 (11)0.25692 (19)0.4805 (9)0.0551 (17)
H70.69770.25000.45400.066*
C80.5058 (12)0.29691 (18)0.4902 (10)0.0567 (17)
C90.3022 (13)0.3086 (2)0.5377 (11)0.067 (2)
C100.2618 (15)0.3473 (2)0.5562 (11)0.072 (2)
H100.12810.35540.59260.086*
C110.4158 (15)0.3734 (2)0.5214 (11)0.073 (2)
H110.38490.39910.53110.087*
C120.6194 (16)0.3620 (2)0.4714 (12)0.082 (2)
H120.72430.37980.44770.098*
C130.6621 (13)0.3239 (2)0.4578 (11)0.067 (2)
H130.79780.31600.42640.081*

Atomic displacement parameters (Å2)

U11U22U33U12U13U23
Zn10.0234 (4)0.0495 (6)0.0370 (5)−0.0006 (4)−0.0002 (3)−0.0018 (4)
N10.064 (4)0.047 (3)0.066 (4)0.013 (3)−0.002 (3)−0.007 (3)
O10.0223 (18)0.062 (3)0.046 (2)0.0040 (17)0.0003 (16)0.003 (2)
O20.037 (2)0.066 (3)0.052 (3)0.003 (2)0.0060 (19)0.018 (2)
O30.032 (2)0.064 (3)0.057 (3)0.0026 (19)−0.0060 (19)−0.011 (2)
O40.085 (4)0.068 (3)0.100 (5)0.013 (3)0.027 (3)0.005 (3)
O50.035 (2)0.079 (3)0.038 (2)0.016 (2)0.0023 (18)0.002 (2)
O60.031 (2)0.099 (4)0.060 (3)−0.005 (2)−0.003 (2)0.030 (3)
O70.029 (2)0.109 (4)0.060 (3)−0.002 (2)−0.004 (2)−0.038 (3)
S10.0239 (7)0.0472 (8)0.0362 (7)0.0032 (6)0.0008 (5)−0.0001 (6)
C10.028 (3)0.047 (3)0.031 (3)0.005 (2)−0.001 (2)−0.005 (2)
C20.039 (3)0.060 (4)0.053 (4)−0.005 (3)−0.010 (3)0.000 (3)
C30.066 (5)0.049 (4)0.069 (5)−0.007 (3)−0.007 (4)−0.012 (3)
C40.053 (4)0.051 (4)0.056 (4)0.012 (3)0.010 (3)−0.002 (3)
C50.046 (4)0.048 (4)0.079 (5)0.007 (3)−0.007 (3)0.000 (3)
C60.037 (3)0.047 (4)0.062 (4)0.005 (3)−0.014 (3)0.001 (3)
C70.058 (4)0.055 (4)0.053 (4)0.008 (3)0.001 (3)−0.005 (3)
C80.068 (4)0.048 (4)0.053 (4)0.003 (4)−0.002 (3)−0.014 (3)
C90.081 (6)0.061 (5)0.058 (5)0.006 (4)0.006 (4)−0.001 (4)
C100.104 (7)0.052 (4)0.059 (5)0.019 (4)0.005 (4)−0.003 (3)
C110.108 (7)0.047 (4)0.062 (5)0.019 (4)−0.006 (4)−0.002 (4)
C120.109 (8)0.052 (5)0.084 (6)0.002 (5)−0.007 (5)0.003 (4)
C130.073 (5)0.059 (5)0.071 (5)0.002 (4)−0.008 (4)−0.007 (4)

Geometric parameters (Å, °)

Zn1—O5i2.054 (4)C1—C21.406 (8)
Zn1—O52.054 (4)C2—C31.391 (9)
Zn1—O7i2.072 (4)C2—H20.9300
Zn1—O72.072 (4)C3—C41.376 (9)
Zn1—O62.073 (4)C3—H30.9300
Zn1—O6i2.073 (4)C4—C51.374 (9)
N1—C71.280 (9)C5—C61.383 (9)
N1—C41.413 (8)C5—H50.9300
O1—S11.453 (4)C6—H60.9300
O2—S11.453 (4)C7—C81.454 (9)
O3—S11.459 (4)C7—H70.9300
O4—C91.332 (9)C8—C131.394 (10)
O4—H40.8200C8—C91.394 (10)
O5—H5A0.8500C9—C101.397 (10)
O5—H5B0.8499C10—C111.365 (11)
O6—H6A0.8500C10—H100.9300
O6—H6B0.8500C11—C121.396 (12)
O7—H7A0.8500C11—H110.9300
O7—H7B0.8500C12—C131.375 (10)
S1—C11.759 (6)C12—H120.9300
C1—C61.380 (8)C13—H130.9300
O5i—Zn1—O5180.0 (2)C3—C2—H2120.6
O5i—Zn1—O7i91.04 (17)C1—C2—H2120.6
O5—Zn1—O7i88.96 (17)C4—C3—C2120.5 (6)
O5i—Zn1—O788.96 (17)C4—C3—H3119.7
O5—Zn1—O791.04 (17)C2—C3—H3119.7
O7i—Zn1—O7180.0 (3)C5—C4—C3119.9 (6)
O5i—Zn1—O689.80 (17)C5—C4—N1117.6 (6)
O5—Zn1—O690.20 (17)C3—C4—N1122.4 (6)
O7i—Zn1—O689.2 (2)C4—C5—C6121.0 (6)
O7—Zn1—O690.8 (2)C4—C5—H5119.5
O5i—Zn1—O6i90.20 (17)C6—C5—H5119.5
O5—Zn1—O6i89.80 (17)C1—C6—C5119.4 (6)
O7i—Zn1—O6i90.8 (2)C1—C6—H6120.3
O7—Zn1—O6i89.2 (2)C5—C6—H6120.3
O6—Zn1—O6i180.0 (3)N1—C7—C8121.9 (7)
C7—N1—C4121.6 (6)N1—C7—H7119.1
C9—O4—H4109.5C8—C7—H7119.1
Zn1—O5—H5A119.3C13—C8—C9119.6 (7)
Zn1—O5—H5B129.9C13—C8—C7119.5 (7)
H5A—O5—H5B106.9C9—C8—C7120.9 (7)
Zn1—O6—H6A128.5O4—C9—C8122.6 (7)
Zn1—O6—H6B119.5O4—C9—C10118.6 (8)
H6A—O6—H6B106.6C8—C9—C10118.8 (8)
Zn1—O7—H7A122.0C11—C10—C9120.9 (8)
Zn1—O7—H7B129.4C11—C10—H10119.5
H7A—O7—H7B106.4C9—C10—H10119.5
O1—S1—O2111.6 (2)C10—C11—C12120.6 (7)
O1—S1—O3112.7 (2)C10—C11—H11119.7
O2—S1—O3112.2 (3)C12—C11—H11119.7
O1—S1—C1106.7 (2)C13—C12—C11118.8 (8)
O2—S1—C1107.2 (3)C13—C12—H12120.6
O3—S1—C1105.9 (2)C11—C12—H12120.6
C6—C1—C2120.4 (5)C12—C13—C8121.2 (8)
C6—C1—S1119.5 (4)C12—C13—H13119.4
C2—C1—S1120.1 (4)C8—C13—H13119.4
C3—C2—C1118.8 (6)
O1—S1—C1—C6163.8 (5)S1—C1—C6—C5177.4 (5)
O2—S1—C1—C6−76.5 (5)C4—C5—C6—C11.4 (10)
O3—S1—C1—C643.5 (5)C4—N1—C7—C8−177.3 (6)
O1—S1—C1—C2−18.6 (5)N1—C7—C8—C13−179.4 (7)
O2—S1—C1—C2101.1 (5)N1—C7—C8—C92.8 (11)
O3—S1—C1—C2−138.9 (5)C13—C8—C9—O4−179.7 (7)
C6—C1—C2—C3−0.7 (9)C7—C8—C9—O4−1.9 (11)
S1—C1—C2—C3−178.3 (5)C13—C8—C9—C10−1.5 (11)
C1—C2—C3—C40.5 (10)C7—C8—C9—C10176.3 (7)
C2—C3—C4—C50.7 (11)O4—C9—C10—C11−179.3 (7)
C2—C3—C4—N1179.1 (6)C8—C9—C10—C112.5 (12)
C7—N1—C4—C5−152.7 (7)C9—C10—C11—C12−1.7 (12)
C7—N1—C4—C328.8 (10)C10—C11—C12—C130.0 (12)
C3—C4—C5—C6−1.7 (11)C11—C12—C13—C80.9 (12)
N1—C4—C5—C6179.8 (6)C9—C8—C13—C12−0.1 (11)
C2—C1—C6—C5−0.2 (9)C7—C8—C13—C12−178.0 (7)

Symmetry codes: (i) −x+2, −y, −z.

Hydrogen-bond geometry (Å, °)

D—H···AD—HH···AD···AD—H···A
O7—H7B···O3ii0.851.932.760 (6)166
O7—H7A···O10.851.932.779 (5)177
O6—H6B···O1iii0.851.922.773 (6)176
O6—H6A···O2iv0.851.922.770 (6)175
O5—H5B···O30.851.902.745 (6)171
O5—H5A···O2iii0.851.912.742 (6)167
O4—H4···N10.821.932.602 (7)139

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

Footnotes

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: PR2013).

References

  • Bruker (1997). SMART (Version 5.044), SAINT (Version 5.01), SADABS (Version 2.0) and SHELXTL (Version 5.10). Bruker AXS Inc., Madison, Wisconsin, USA.
  • Sheldrick, G. M. (1997). SHELXS97 and SHELXL97 University of Göttingen, Germany.
  • Tai, X. S., Liu, W. Y., Liu, Y. Z. & Li, Y. Z. (2005). Acta Cryst. E61, o389–o390.

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