metal-organic compounds\(\def\hfill{\hskip 5em}\def\hfil{\hskip 3em}\def\eqno#1{\hfil {#1}}\)

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Di­aqua­bis­(cyclo­hexa­ne­carboxyl­ato)zinc(II) monohydrate

aEngineering Research Center for Clean Production of Textile Dyeing and Printing, Ministry of Education, Wuhan 430073, People's Republic of China
*Correspondence e-mail: qfzeng@wuse.edu.cn

(Received 20 August 2009; accepted 22 August 2009; online 29 August 2009)

In the title compound, [Zn(C7H11O2)2(H2O)2]·H2O, the ZnII atom (site symmetry [\overline{1}]) is four-coordinated by two O atoms from the cyclo­hexa­necarboxyl­ate anions and two O atoms from the water mol­ecules, forming a slightly distorted square-planar coordination. The O atom of the uncoordinated water mol­ecule lies on a crysatllographic twofold rotation axis. In the crystal, the components are linked by O—H⋯O hydrogen bonds, forming a three-dimensional network.

Related literature

For background, see: Cheng et al. (2006[Cheng, K., Zhu, H.-L. & Li, Y.-G. (2006). Z. Anorg. Allg. Chem. 632, 2326-2330.]). For reference structural data, see: Allen et al. (1987[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.]).

[Scheme 1]

Experimental

Crystal data
  • [Zn(C7H11O2)2(H2O)2]·H2O

  • Mr = 373.75

  • Monoclinic, P 2/c

  • a = 15.9045 (16) Å

  • b = 4.9295 (6) Å

  • c = 11.5335 (16) Å

  • β = 91.585 (6)°

  • V = 903.89 (19) Å3

  • Z = 2

  • Mo Kα radiation

  • μ = 1.39 mm−1

  • T = 296 K

  • 0.28 × 0.25 × 0.22 mm

Data collection
  • Enraf–Nonius CAD-4 diffractometer

  • Absorption correction: ψ scan (North et al., 1968[North, A. C. T., Phillips, D. C. & Mathews, F. S. (1968). Acta Cryst. A24, 351-359.]) Tmin = 0.698, Tmax = 0.750

  • 4764 measured reflections

  • 1752 independent reflections

  • 1436 reflections with I > 2σ(I)

  • Rint = 0.032

  • 200 standard reflections every 3 reflections intensity decay: 1%

Refinement
  • R[F2 > 2σ(F2)] = 0.054

  • wR(F2) = 0.158

  • S = 1.07

  • 1752 reflections

  • 114 parameters

  • 4 restraints

  • H atoms treated by a mixture of independent and constrained refinement

  • Δρmax = 1.00 e Å−3

  • Δρmin = −0.37 e Å−3

Table 1
Selected bond lengths (Å)

Zn1—O2 1.961 (3)
Zn1—O3 1.977 (4)

Table 2
Hydrogen-bond geometry (Å, °)

D—H⋯A D—H H⋯A DA D—H⋯A
O7—H7⋯O1 0.834 (10) 1.99 (3) 2.699 (4) 142 (5)
O3—H3D⋯O1i 0.846 (10) 2.53 (7) 3.132 (6) 129 (8)
O3—H3C⋯O7ii 0.853 (10) 2.17 (2) 2.997 (5) 164 (6)
Symmetry codes: (i) [x, -y+1, z-{\script{1\over 2}}]; (ii) -x+1, -y+2, -z.

Data collection: CAD-4 Software (Enraf–Nonius, 1989[Enraf-Nonius (1989). CAD-4 Software. Enraf-Nonius, Delft, The Netherlands.]); cell refinement: CAD-4 Software; data reduction: XCAD4 (Harms & Wocadlo, 1995[Harms, K. & Wocadlo, S. (1995). XCAD4. University of Marburg, Germany.]); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); molecular graphics: SHELXTL (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); software used to prepare material for publication: SHELXTL.

Supporting information


Comment top

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 cyclohexanecarboxylate and two O atoms from the water molecules, forming a slightly distorted square-planar coordination (Table 1). In the crystal, O—H···O hydrogen bonds (Table 2) link the components.

Related literature top

For background, see: Cheng et al. (2006). For reference structural data, see: Allen et al. (1987).

Experimental top

A mixture of cyclohexanecarboxylic acid (256 mg, 2 mmol) and ZnNO3.6H2O (1 mmol, 297 mg) in methanol (10 ml) was stirred for 2 h. After keeping the filtrate in air for 6 d, colourless blocks of (I) were formed.

Refinement top

The O-bound H atoms were located in a difference map and their positions were refined with the restraint O—H = 0.82 (1)Å. The other H atoms were positioned geometrically (C—H = 0.97–0.98Å) and refined as riding, with Uiso(H) = 1.2Ueq(carrier).

Computing details top

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

Figures top
[Figure 1] Fig. 1. The molecular structure of (I) showing 30% probability displacement ellipsoids. Atoms with the suffix A are generated by the symmetry code (1–x, 1–y, –z).
Diaquabis(cyclohexanecarboxylato)zinc(II) monohydrate top
Crystal data top
[Zn(C7H11O2)2(H2O)2]·H2OF(000) = 396
Mr = 373.75Dx = 1.373 Mg m3
Monoclinic, P2/cMo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ycCell parameters from 25 reflections
a = 15.9045 (16) Åθ = 9–12°
b = 4.9295 (6) ŵ = 1.39 mm1
c = 11.5335 (16) ÅT = 296 K
β = 91.585 (6)°Block, colorless
V = 903.89 (19) Å30.28 × 0.25 × 0.22 mm
Z = 2
Data collection top
Enraf–Nonius CAD-4
diffractometer
1436 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tubeRint = 0.032
Graphite monochromatorθmax = 26.0°, θmin = 2.6°
ω/2θ scansh = 1819
Absorption correction: ψ scan
(North et al., 1968)
k = 66
Tmin = 0.698, Tmax = 0.750l = 1214
4764 measured reflections200 standard reflections every 3 reflections
1752 independent reflections intensity decay: 1%
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)] = 0.054Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.158H atoms treated by a mixture of independent and constrained refinement
S = 1.07 w = 1/[σ2(Fo2) + (0.0809P)2 + 1.216P]
where P = (Fo2 + 2Fc2)/3
1752 reflections(Δ/σ)max = 0.003
114 parametersΔρmax = 1.00 e Å3
4 restraintsΔρmin = 0.37 e Å3
Crystal data top
[Zn(C7H11O2)2(H2O)2]·H2OV = 903.89 (19) Å3
Mr = 373.75Z = 2
Monoclinic, P2/cMo Kα radiation
a = 15.9045 (16) ŵ = 1.39 mm1
b = 4.9295 (6) ÅT = 296 K
c = 11.5335 (16) Å0.28 × 0.25 × 0.22 mm
β = 91.585 (6)°
Data collection top
Enraf–Nonius CAD-4
diffractometer
1436 reflections with I > 2σ(I)
Absorption correction: ψ scan
(North et al., 1968)
Rint = 0.032
Tmin = 0.698, Tmax = 0.750200 standard reflections every 3 reflections
4764 measured reflections intensity decay: 1%
1752 independent reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0544 restraints
wR(F2) = 0.158H atoms treated by a mixture of independent and constrained refinement
S = 1.07Δρmax = 1.00 e Å3
1752 reflectionsΔρmin = 0.37 e Å3
114 parameters
Special details top

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) top
xyzUiso*/Ueq
C10.2156 (3)0.3294 (12)0.0060 (4)0.0586 (12)
H1A0.24630.28240.07470.070*
H1B0.21260.52560.00170.070*
C20.1273 (3)0.2162 (13)0.0177 (4)0.0711 (14)
H2A0.09880.29660.08470.085*
H2B0.13010.02180.03000.085*
C30.0779 (3)0.2734 (13)0.0889 (5)0.0743 (15)
H3A0.07090.46760.09800.089*
H3B0.02260.19170.08100.089*
C40.1236 (3)0.1592 (16)0.1934 (5)0.0832 (18)
H4A0.12640.03670.18640.100*
H4B0.09250.20170.26220.100*
C50.2124 (3)0.2720 (13)0.2071 (4)0.0661 (14)
H5A0.20950.46530.22210.079*
H5B0.24050.18670.27330.079*
C60.2630 (2)0.2234 (9)0.0999 (3)0.0427 (9)
H60.27080.02740.09080.051*
C70.3485 (2)0.3560 (8)0.1063 (4)0.0455 (9)
H70.475 (3)0.722 (8)0.205 (3)0.058 (14)*
O10.3660 (3)0.5302 (7)0.1802 (4)0.0755 (11)
O20.39946 (17)0.2822 (6)0.0283 (3)0.0549 (8)
O30.4282 (3)0.7551 (8)0.0904 (4)0.0718 (10)
O70.50000.8302 (10)0.25000.0775 (16)
Zn10.50000.50000.00000.0492 (3)
H3D0.384 (3)0.71 (2)0.127 (5)0.18 (5)*
H3C0.457 (3)0.852 (11)0.136 (4)0.076 (18)*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
C10.045 (2)0.085 (4)0.046 (2)0.007 (2)0.0019 (18)0.005 (2)
C20.048 (3)0.097 (4)0.067 (3)0.012 (3)0.011 (2)0.006 (3)
C30.037 (2)0.094 (4)0.092 (4)0.003 (2)0.000 (2)0.010 (3)
C40.057 (3)0.120 (5)0.075 (3)0.017 (3)0.026 (3)0.004 (4)
C50.053 (3)0.101 (4)0.045 (2)0.002 (3)0.005 (2)0.002 (2)
C60.0374 (19)0.046 (2)0.045 (2)0.0065 (16)0.0017 (16)0.0002 (17)
C70.041 (2)0.041 (2)0.054 (2)0.0016 (17)0.0066 (18)0.0067 (19)
O10.065 (2)0.074 (3)0.086 (3)0.0155 (18)0.0144 (19)0.0217 (19)
O20.0323 (14)0.0504 (17)0.083 (2)0.0060 (12)0.0125 (14)0.0045 (15)
O30.060 (2)0.066 (2)0.089 (3)0.0020 (18)0.004 (2)0.012 (2)
O70.047 (3)0.041 (3)0.143 (5)0.0000.008 (3)0.000
Zn10.0317 (4)0.0478 (4)0.0684 (5)0.0007 (3)0.0066 (3)0.0097 (3)
Geometric parameters (Å, º) top
C1—C61.511 (6)C5—H5A0.9700
C1—C21.513 (6)C5—H5B0.9700
C1—H1A0.9700C6—C71.509 (5)
C1—H1B0.9700C6—H60.9800
C2—C31.503 (7)C7—O11.236 (5)
C2—H2A0.9700C7—O21.281 (5)
C2—H2B0.9700Zn1—O21.961 (3)
C3—C41.500 (8)Zn1—O31.977 (4)
C3—H3A0.9700O3—H3D0.846 (10)
C3—H3B0.9700O3—H3C0.853 (10)
C4—C51.521 (7)O7—H70.834 (10)
C4—H4A0.9700Zn1—O2i1.961 (3)
C4—H4B0.9700Zn1—O3i1.977 (4)
C5—C61.513 (6)
C6—C1—C2112.6 (4)C6—C5—H5A109.3
C6—C1—H1A109.1C4—C5—H5A109.3
C2—C1—H1A109.1C6—C5—H5B109.3
C6—C1—H1B109.1C4—C5—H5B109.3
C2—C1—H1B109.1H5A—C5—H5B107.9
H1A—C1—H1B107.8C7—C6—C1108.6 (3)
C3—C2—C1111.3 (4)C7—C6—C5113.0 (4)
C3—C2—H2A109.4C1—C6—C5110.0 (4)
C1—C2—H2A109.4C7—C6—H6108.4
C3—C2—H2B109.4C1—C6—H6108.4
C1—C2—H2B109.4C5—C6—H6108.4
H2A—C2—H2B108.0O1—C7—O2123.1 (4)
C4—C3—C2109.5 (4)O1—C7—C6121.4 (4)
C4—C3—H3A109.8O2—C7—C6115.5 (4)
C2—C3—H3A109.8C7—O2—Zn1119.8 (3)
C4—C3—H3B109.8Zn1—O3—H3D123 (6)
C2—C3—H3B109.8Zn1—O3—H3C112 (4)
H3A—C3—H3B108.2H3D—O3—H3C107.5 (17)
C3—C4—C5112.0 (5)O2—Zn1—O2i180.0
C3—C4—H4A109.2O2—Zn1—O388.54 (15)
C5—C4—H4A109.2O2i—Zn1—O391.46 (15)
C3—C4—H4B109.2O2—Zn1—O3i91.46 (15)
C5—C4—H4B109.2O2i—Zn1—O3i88.54 (15)
H4A—C4—H4B107.9O3—Zn1—O3i180.0
C6—C5—C4111.7 (4)
C6—C1—C2—C356.4 (6)C5—C6—C7—O114.3 (6)
C1—C2—C3—C456.7 (7)C1—C6—C7—O269.8 (5)
C2—C3—C4—C557.1 (7)C5—C6—C7—O2167.9 (4)
C3—C4—C5—C656.2 (7)O1—C7—O2—Zn113.6 (6)
C2—C1—C6—C7177.8 (4)C6—C7—O2—Zn1164.1 (3)
C2—C1—C6—C553.7 (6)C7—O2—Zn1—O2i115 (24)
C4—C5—C6—C7174.6 (5)C7—O2—Zn1—O379.1 (3)
C4—C5—C6—C153.1 (6)C7—O2—Zn1—O3i100.9 (3)
C1—C6—C7—O1107.9 (5)
Symmetry code: (i) x+1, y+1, z.
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
O7—H7···O10.83 (1)1.99 (3)2.699 (4)142 (5)
O3—H3D···O1ii0.85 (1)2.53 (7)3.132 (6)129 (8)
O3—H3C···O7iii0.85 (1)2.17 (2)2.997 (5)164 (6)
Symmetry codes: (ii) x, y+1, z1/2; (iii) x+1, y+2, z.

Experimental details

Crystal data
Chemical formula[Zn(C7H11O2)2(H2O)2]·H2O
Mr373.75
Crystal system, space groupMonoclinic, P2/c
Temperature (K)296
a, b, c (Å)15.9045 (16), 4.9295 (6), 11.5335 (16)
β (°) 91.585 (6)
V3)903.89 (19)
Z2
Radiation typeMo Kα
µ (mm1)1.39
Crystal size (mm)0.28 × 0.25 × 0.22
Data collection
DiffractometerEnraf–Nonius CAD-4
diffractometer
Absorption correctionψ scan
(North et al., 1968)
Tmin, Tmax0.698, 0.750
No. of measured, independent and
observed [I > 2σ(I)] reflections
4764, 1752, 1436
Rint0.032
(sin θ/λ)max1)0.617
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.054, 0.158, 1.07
No. of reflections1752
No. of parameters114
No. of restraints4
H-atom treatmentH atoms treated by a mixture of independent and constrained refinement
Δρmax, Δρmin (e Å3)1.00, 0.37

Computer programs: CAD-4 Software (Enraf–Nonius, 1989), XCAD4 (Harms & Wocadlo, 1995), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), SHELXTL (Sheldrick, 2008).

Selected bond lengths (Å) top
Zn1—O21.961 (3)Zn1—O31.977 (4)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
O7—H7···O10.834 (10)1.99 (3)2.699 (4)142 (5)
O3—H3D···O1i0.846 (10)2.53 (7)3.132 (6)129 (8)
O3—H3C···O7ii0.853 (10)2.17 (2)2.997 (5)164 (6)
Symmetry codes: (i) x, y+1, z1/2; (ii) x+1, y+2, z.
 

Acknowledgements

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).

References

First citationAllen, F. H., Kennard, O., Watson, D. G., Brammer, L., Orpen, A. G. & Taylor, R. (1987). J. Chem. Soc. Perkin Trans. 2, pp. S1–19.  CrossRef Web of Science
First citationCheng, K., Zhu, H.-L. & Li, Y.-G. (2006). Z. Anorg. Allg. Chem. 632, 2326–2330.  Web of Science CSD CrossRef
First citationEnraf–Nonius (1989). CAD-4 Software. Enraf–Nonius, Delft, The Netherlands.
First citationHarms, K. & Wocadlo, S. (1995). XCAD4. University of Marburg, Germany.
First citationNorth, A. C. T., Phillips, D. C. & Mathews, F. S. (1968). Acta Cryst. A24, 351–359.  CrossRef IUCr Journals Web of Science
First citationSheldrick, G. M. (2008). Acta Cryst. A64, 112–122.  Web of Science CrossRef CAS IUCr Journals

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