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Acta Crystallogr Sect E Struct Rep Online. 2009 September 1; 65(Pt 9): m1146.
Published online 2009 August 29. doi:  10.1107/S1600536809033650
PMCID: PMC2970116

Bis{2-[2-(dimethyl­amino)ethyl­imino­meth­yl]-4,6-disulfanylphenolato}cobalt(II) monohydrate

Abstract

In the title hydrated complex, [Co(C11H15N2OS2)2]·H2O, the CoII atom (site symmetry 2) is coordinated by two O,N,N′-tridentate Schiff base ligands, resulting in a very distorted cis-CoO2N4 octa­hedral geometry for the metal ion. In the crystal, the water mol­ecule (O-atom site symmetry 2) inter­acts with nearby complex mol­ecules by way of bifurcated O—H(...)(O,S) hydrogen bonds.

Related literature

For a related compound and background, see: Li et al. (2009 [triangle]). For reference structural data, see: Allen et al. (1987 [triangle]).

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Object name is e-65-m1146-scheme1.jpg

Experimental

Crystal data

  • [Co(C11H15N2OS2)2]·H2O
  • M r = 587.69
  • Orthorhombic, An external file that holds a picture, illustration, etc.
Object name is e-65-m1146-efi1.jpg
  • a = 12.3755 (15) Å
  • b = 9.2485 (15) Å
  • c = 22.827 (3) Å
  • V = 2612.7 (6) Å3
  • Z = 4
  • Mo Kα radiation
  • μ = 1.01 mm−1
  • T = 296 K
  • 0.30 × 0.25 × 0.25 mm

Data collection

  • Enraf–Nonius CAD-4 diffractometer
  • Absorption correction: ψ scan (North et al., 1968 [triangle]) T min = 0.752, T max = 0.787
  • 13847 measured reflections
  • 2548 independent reflections
  • 2039 reflections with I > 2σ(I)
  • R int = 0.031
  • 200 standard reflections every 3 reflections intensity decay: 1%

Refinement

  • R[F 2 > 2σ(F 2)] = 0.054
  • wR(F 2) = 0.186
  • S = 1.06
  • 2548 reflections
  • 160 parameters
  • 1 restraint
  • H atoms treated by a mixture of independent and constrained refinement
  • Δρmax = 0.84 e Å−3
  • Δρmin = −0.96 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/S1600536809033650/hb5056sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809033650/hb5056Isup2.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

As part of our onging studies of this family of compounds (Li et al., 2009), 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 Co(II) is six-coordinated in a distorted octhaedral coordination by two N,N,O-tridentate Schiff base ligands.

Experimental

A mixture of 2-hydroxy-3,5-dimercaptobenzaldehyde (372 mg, 2 mmol), N,N-dimethylethane-1,2-diamine (176 mg, 2 mmol) and CoCl2.6H2O (1 mmol, 238 mg) in methanol (10 ml) was stirred for 1 h. After keeping the filtrate in air for 7 d, red blocks of (I) were formed.

Refinement

The water H atom was located in a difference map and its position was freely refined. All other H atoms were positioned geometrically (C—H = 0.93–0.97Å, S—H = 1.2Å) and refined as riding, with Uiso(H) = 1.2Ueq(carrier) or 1.5Ueq(methyl C).

Figures

Fig. 1.
The molecular structure of (I) showing 30% probability displacement ellipsoids. Atoms with the suffix A are generated by the symmetry operation (1–x, y, 3/2–z).

Crystal data

[Co(C11H15N2OS2)2]·H2OF(000) = 1228
Mr = 587.69Dx = 1.494 Mg m3
Orthorhombic, PbcnMo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2n 2abCell parameters from 25 reflections
a = 12.3755 (15) Åθ = 9–12°
b = 9.2485 (15) ŵ = 1.01 mm1
c = 22.827 (3) ÅT = 296 K
V = 2612.7 (6) Å3Block, red
Z = 40.30 × 0.25 × 0.25 mm

Data collection

Enraf–Nonius CAD-4 diffractometer2039 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tubeRint = 0.031
graphiteθmax = 26.0°, θmin = 2.4°
ω/2θ scansh = −15→15
Absorption correction: ψ scan (North et al., 1968)k = −11→6
Tmin = 0.752, Tmax = 0.787l = −28→27
13847 measured reflections200 standard reflections every 3 reflections
2548 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)] = 0.054Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.186H atoms treated by a mixture of independent and constrained refinement
S = 1.06w = 1/[σ2(Fo2) + (0.1201P)2 + 2.1692P] where P = (Fo2 + 2Fc2)/3
2548 reflections(Δ/σ)max = 0.001
160 parametersΔρmax = 0.84 e Å3
1 restraintΔρmin = −0.96 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
C30.2776 (3)0.1848 (3)0.68222 (16)0.0417 (8)
H30.20820.22070.67680.050*
C40.4167 (3)0.0107 (3)0.64302 (14)0.0380 (7)
C50.3168 (3)0.0854 (4)0.63802 (14)0.0395 (7)
C60.4439 (3)−0.0791 (4)0.59437 (15)0.0467 (9)
C70.2502 (3)0.0634 (4)0.58895 (17)0.0524 (10)
H70.18460.11200.58660.063*
C80.2678 (3)0.3286 (4)0.76616 (19)0.0507 (9)
H8A0.22450.27390.79380.061*
H8B0.21950.38810.74290.061*
C90.3788 (4)−0.0974 (4)0.54666 (16)0.0588 (11)
H90.4004−0.15600.51570.071*
C100.2796 (4)−0.0272 (5)0.54503 (18)0.0623 (12)
C110.3458 (3)0.4236 (4)0.79892 (18)0.0514 (9)
H11A0.37910.49090.77180.062*
H11B0.30660.47950.82790.062*
C140.5090 (4)0.4381 (5)0.8533 (2)0.0673 (13)
H14A0.53390.50320.82340.101*
H14B0.56920.38470.86860.101*
H14C0.47570.49220.88420.101*
C150.3836 (4)0.2501 (5)0.87496 (19)0.0651 (12)
H15A0.33750.30910.89890.098*
H15B0.44020.21000.89870.098*
H15C0.34210.17320.85790.098*
Co10.50000.18183 (7)0.75000.0390 (3)
H2A0.502 (3)0.789 (4)0.7815 (11)0.059 (14)*
N10.4310 (2)0.3386 (3)0.82838 (13)0.0431 (7)
N20.3272 (2)0.2283 (3)0.72746 (13)0.0401 (6)
O10.48006 (19)0.0189 (3)0.68755 (11)0.0412 (6)
O20.50000.7436 (5)0.75000.0605 (11)*
S10.19385 (15)−0.05824 (19)0.48627 (6)0.0990 (6)
H10.11070.00610.49370.148*
S20.56823 (10)−0.16647 (13)0.59645 (5)0.0678 (4)
H20.5567−0.28600.61590.102*

Atomic displacement parameters (Å2)

U11U22U33U12U13U23
C30.0367 (18)0.0393 (18)0.049 (2)−0.0001 (13)−0.0046 (14)0.0043 (14)
C40.0496 (19)0.0308 (15)0.0336 (16)−0.0073 (14)−0.0017 (14)0.0007 (12)
C50.0439 (18)0.0357 (16)0.0391 (17)−0.0069 (14)−0.0053 (14)0.0024 (13)
C60.062 (2)0.0407 (18)0.0372 (17)−0.0006 (16)0.0042 (16)−0.0029 (14)
C70.055 (2)0.054 (2)0.048 (2)−0.0105 (18)−0.0152 (17)0.0112 (16)
C80.042 (2)0.055 (2)0.056 (2)0.0115 (16)0.0015 (17)−0.0060 (17)
C90.086 (3)0.053 (2)0.0371 (19)−0.012 (2)−0.0050 (19)−0.0067 (16)
C100.085 (3)0.061 (2)0.041 (2)−0.021 (2)−0.022 (2)0.0033 (18)
C110.057 (2)0.0418 (19)0.055 (2)0.0080 (17)0.0037 (18)−0.0054 (16)
C140.056 (3)0.068 (3)0.078 (3)−0.004 (2)0.003 (2)−0.028 (2)
C150.076 (3)0.066 (3)0.054 (2)0.011 (2)0.018 (2)0.004 (2)
Co10.0383 (4)0.0381 (4)0.0406 (4)0.000−0.0028 (2)0.000
N10.0433 (16)0.0398 (15)0.0462 (16)0.0012 (12)0.0001 (13)−0.0065 (12)
N20.0376 (15)0.0375 (14)0.0452 (16)0.0029 (11)−0.0013 (12)−0.0018 (13)
O10.0498 (13)0.0367 (12)0.0372 (12)0.0030 (10)−0.0080 (10)−0.0059 (10)
S10.1182 (13)0.1170 (13)0.0616 (8)−0.0154 (9)−0.0498 (8)−0.0119 (7)
S20.0758 (8)0.0646 (7)0.0629 (7)0.0195 (6)0.0044 (5)−0.0196 (5)

Geometric parameters (Å, °)

C3—N21.267 (5)C11—H11A0.9700
C3—C51.449 (5)C11—H11B0.9700
C3—H30.9300C14—N11.449 (5)
C4—O11.286 (4)C14—H14A0.9600
C4—C51.421 (5)C14—H14B0.9600
C4—C61.427 (5)C14—H14C0.9600
C5—C71.406 (5)C15—N11.464 (5)
C6—C91.366 (5)C15—H15A0.9600
C6—S21.738 (4)C15—H15B0.9600
C7—C101.356 (6)C15—H15C0.9600
C7—H70.9300Co1—O12.089 (2)
C8—N21.477 (5)Co1—O1i2.089 (2)
C8—C111.505 (6)Co1—N2i2.241 (3)
C8—H8A0.9700Co1—N22.241 (3)
C8—H8B0.9700Co1—N12.456 (3)
C9—C101.389 (7)Co1—N1i2.456 (3)
C9—H90.9300O2—H2A0.832 (10)
C10—S11.735 (4)S1—H11.2000
C11—N11.478 (5)S2—H21.2000
N2—C3—C5127.4 (3)H11A—C11—H11B107.9
N2—C3—H3116.3N1—C14—H14A109.5
C5—C3—H3116.3N1—C14—H14B109.5
O1—C4—C5124.4 (3)H14A—C14—H14B109.5
O1—C4—C6120.4 (3)N1—C14—H14C109.5
C5—C4—C6115.2 (3)H14A—C14—H14C109.5
C7—C5—C4120.2 (3)H14B—C14—H14C109.5
C7—C5—C3116.8 (3)N1—C15—H15A109.5
C4—C5—C3123.0 (3)N1—C15—H15B109.5
C9—C6—C4123.6 (4)H15A—C15—H15B109.5
C9—C6—S2119.1 (3)N1—C15—H15C109.5
C4—C6—S2117.3 (3)H15A—C15—H15C109.5
C10—C7—C5121.4 (4)H15B—C15—H15C109.5
C10—C7—H7119.3O1—Co1—O1i87.65 (14)
C5—C7—H7119.3O1—Co1—N2i114.06 (10)
N2—C8—C11110.2 (3)O1i—Co1—N2i82.47 (10)
N2—C8—H8A109.6O1—Co1—N282.48 (10)
C11—C8—H8A109.6O1i—Co1—N2114.06 (10)
N2—C8—H8B109.6N2i—Co1—N2157.88 (15)
C11—C8—H8B109.6N1—Co1—O1151.87 (12)
H8A—C8—H8B108.1N1—Co1—N273.88 (12)
C6—C9—C10119.0 (4)N1—Co1—N1i107.64 (12)
C6—C9—H9120.5C14—N1—C15109.7 (4)
C10—C9—H9120.5C14—N1—C11108.4 (3)
C7—C10—C9120.4 (4)C15—N1—C11110.0 (3)
C7—C10—S1120.7 (4)C3—N2—C8116.5 (3)
C9—C10—S1118.9 (3)C3—N2—Co1126.0 (2)
N1—C11—C8111.9 (3)C8—N2—Co1117.3 (2)
N1—C11—H11A109.2C4—O1—Co1130.8 (2)
C8—C11—H11A109.2C10—S1—H1109.5
N1—C11—H11B109.2C6—S2—H2109.5
C8—C11—H11B109.2

Symmetry codes: (i) −x+1, y, −z+3/2.

Hydrogen-bond geometry (Å, °)

D—H···AD—HH···AD···AD—H···A
O2—H2A···S2ii0.83 (1)2.95 (2)3.7001 (17)151 (4)
O2—H2A···O1ii0.83 (1)2.25 (3)2.928 (5)139 (4)

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

Footnotes

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: HB5056).

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.
  • Enraf–Nonius (1989). CAD-4 Software Enraf–Nonius, Delft, The Netherlands.
  • Harms, K. & Wocadlo, S. (1995). XCAD4 University of Marburg, Germany.
  • Li, H.-Y., Wang, L.-J., Hou, J. & Zeng, Q.-F. (2009). Acta Cryst. E65, m1112. [PMC free article] [PubMed]
  • 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