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Acta Cryst. (2007). E63, m2117    [ doi:10.1107/S160053680703276X ]

Tris(4-morpholinecarbodithioato-[kappa]2S,S')cobalt(III)

A. Kropidlowska, J. Chojnacki, J. Golaszewska, D. Paliwoda and B. Becker

Abstract top

In the unsolvated title compound, [Co(C5H8NOS2)3], the CoIII ion is coordinated by three chelating dithiocarbamate ligands. The central CoS6 core forms a trigonally distorted octahedron.

Comment top

Dithiocarbamates (dtc) react with many metallic ions and the complexing properties of these ligands are directly related to the presence of two donor S atoms. The dithiocarbamates serve different analytical purposes-the more interesting properties occur with disubstituted dithiocarbamates since the monosubstituted compounds show stronger reducing properties and tend to decompose to hydrogen sulfide (Hulanicki, 1967). Microdetermination of some metals such as Ni, Co, Fe, Cd or Zn using 4-morpholinecarbodithioate have been described (Sakla et al. 1979, Cadore et al., 2005.). What more, cobalt dithiocarbamates, such as aforementioned morpholine derivative, were used as catalyst systems for producing polybutadiene of a high degree of polymerization (Nasirov, 2003).

The structures of solvated tris(4-morpholinecarbodithioato-κ2S,S')cobalt(III) complexes have been described previously: with CHCl3 (Zhang et al., 2001), C6H6 (Butcher & Sinn, 1976) and CH2Cl2 (Healy & Sinn, 1975) as solvating molecules. Recently, we have devoted our interest to complexes with dtc ligands and we present here the structure of unsolvated [Co(S2CNC4H8O)3] complex, (I) (Fig. 1).

Monoclinic crystals of this mononuclear complex are built of [Co(S2CN(C4H8O)3] units with cobalt octahedrally coordinated by three bidentate dithiocarbamate ligands. The title compound possess D3 pseudosymmetry. The deformation of the coordination geometry is undoubtedly caused by the presence of three chelating agents and thus imposed S—Co—S bite angles. It is noteworthy that (I) which was recrystallized from chloroform did not retain the solvent within its crystal structure, unlike related tris(1-pyrrolidinylcarbodithioato-S,S')-cobalt(III) chloroform disolvate (Kropidłowska et al., 2007) reported by us earlier. Molecules of (I) are instead tightly packed (Fig. 2) forming layers (Fig. 3). Many short C—H···S contacts (with C···S distance of ca. 3.5 – 3.9 Å) are present between the adjacent layers. Some C—H···S interactions in the dithicarbamate cases have been observed and discussed previously (Healy et al., 1990). Several C—H···O short contacts (with C···O distance of ca. 3.1 – 3.5 Å) are present as well.

Related literature top

For related literature, see: Zhang et al. (2001); Butcher & Sinn (1976); Healy & Sinn (1975); Cadore et al. (2005); Healy et al. (1990); Hulanicki (1967); Kropidłowska et al. (2007); Nasirov (2003); Sakla et al. (1979).

Experimental top

The complexing agent was obtained by conventional method from the reaction between carbon disulfide (Merck), morpholine (Merck) and potassium hydroxide (POCh) at 0°C, under constant stirring. The product was filtered, washed with cold methanol and recrystallized from the same solvent. Cobalt chloride, CoCl2×6H2O (0.58 g, 0.0025 mol) purchased from POCh) was dissolved in 50 ml of methanol/water (10/1, v/v) and this solution was added dropwise to the potassium salt of morpholinecarbodithioic acid OC4H8NCS2K (0.98 g, 0.005 mol, Fluka) dissolved in methanol/water (10/1, v/v). The mixture was stirred vigorously in an inert gas (Ar) atmosphere for 25 minutes. The solution was then filtered and filtrate left for crystallization at 5°C. After a week green crystals were collected.

Refinement top

All H atoms were placed in calculated positions (0.99 Å) and refined as riding with Uiso(H) = 1.3Ueq (methylene carrier).

The highest peak in the difference map is 0.05 Å from Co1 and the largest hole is 1.56 Å from S5.

Computing details top

Data collection: CrysAlis CCD (Oxford Diffraction, 2006); cell refinement: CrysAlis RED; data reduction: CrysAlis RED; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997) and Mercury (Macrae et al., 2006); software used to prepare material for publication: WinGX (Farrugia, 1999).

Figures top
[Figure 1] Fig. 1. Molecular structure of (I), with displacement ellipsoids drawn at the 50% probability level.
[Figure 2] Fig. 2. Schematic drawing of the crystal packing of I viewed along a axis.
[Figure 3] Fig. 3. Schematic drawing of the crystal packing of I viewed along b axis.
Tris(4-morpholinecarbodithioato-κ2S,S')cobalt(III) top
Crystal data top
[Co(C5H8NOS2)3]Z = 4
Mr = 545.66F(000) = 1128
Monoclinic, P21/cDx = 1.552 Mg m−3
Hall symbol: -P 2ybcMo Kα radiation, λ = 0.71073 Å
a = 13.1952 (6) Åθ = 2.4–32.5°
b = 11.4668 (5) ŵ = 1.29 mm−1
c = 15.7281 (9) ÅT = 120 K
β = 101.006 (5)°Prism, dark green
V = 2336.0 (2) Å30.19 × 0.10 × 0.02 mm
Data collection top
Oxford Diffraction KM4 CCD area-detector
diffractometer		4538 independent reflections
graphite4094 reflections with I > 2σ(I)
Detector resolution: 8.1883 pixels mm-1Rint = 0.039
ω scans, 0.75 deg widthθmax = 26°, θmin = 2.4°
Absorption correction: analytical
[CrysAlis RED (Oxford Diffraction, 2006); analytical numerical absorption correction using a multifaceted crystal model (Clark & Reid, 1995)]		h = −16→15
Tmin = 0.74, Tmax = 0.9k = −13→14
12971 measured reflectionsl = −19→15
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)] = 0.049Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.131H-atom parameters constrained
S = 1.13 w = 1/[σ2(Fo2) + (0.0719P)2 + 4.281P]
where P = (Fo2 + 2Fc2)/3
4538 reflections(Δ/σ)max < 0.001
253 parametersΔρmax = 1.11 e Å−3
0 restraintsΔρmin = −0.82 e Å−3
Crystal data top
[Co(C5H8NOS2)3]V = 2336.0 (2) Å3
Mr = 545.66Z = 4
Monoclinic, P21/cMo Kα radiation
a = 13.1952 (6) ŵ = 1.29 mm−1
b = 11.4668 (5) ÅT = 120 K
c = 15.7281 (9) Å0.19 × 0.10 × 0.02 mm
β = 101.006 (5)°
Data collection top
Oxford Diffraction KM4 CCD area-detector
diffractometer		4538 independent reflections
Absorption correction: analytical
[CrysAlis RED (Oxford Diffraction, 2006); analytical numerical absorption correction using a multifaceted crystal model (Clark & Reid, 1995)]		4094 reflections with I > 2σ(I)
Tmin = 0.74, Tmax = 0.9Rint = 0.039
12971 measured reflectionsθmax = 26°
Refinement top
R[F2 > 2σ(F2)] = 0.049H-atom parameters constrained
wR(F2) = 0.131Δρmax = 1.11 e Å−3
S = 1.13Δρmin = −0.82 e Å−3
4538 reflectionsAbsolute structure: ?
253 parametersFlack parameter: ?
0 restraintsRogers parameter: ?
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
Co10.26983 (3)0.01485 (4)0.26399 (3)0.01532 (14)
S10.42699 (6)0.10412 (7)0.28576 (5)0.0203 (2)
S20.30882 (6)0.03786 (7)0.40951 (5)0.01715 (19)
S30.33634 (6)−0.16687 (7)0.25782 (5)0.01816 (19)
S40.13436 (6)−0.10359 (7)0.27236 (5)0.01796 (19)
S50.23133 (6)0.03742 (7)0.11798 (5)0.01843 (19)
S60.17989 (6)0.18432 (7)0.24632 (5)0.01834 (19)
N10.4846 (2)0.1614 (3)0.45449 (17)0.0203 (6)
N20.1923 (2)−0.3293 (2)0.27148 (19)0.0216 (6)
N30.1270 (2)0.2387 (2)0.07649 (17)0.0221 (6)
O10.5547 (2)0.3653 (2)0.54704 (17)0.0362 (6)
O20.1546 (2)−0.5539 (2)0.33120 (16)0.0276 (5)
O3−0.0211 (2)0.3479 (2)−0.05188 (15)0.0292 (6)
C10.4184 (2)0.1095 (3)0.3928 (2)0.0171 (6)
C20.5761 (3)0.2238 (3)0.4379 (2)0.0246 (7)
H2A0.58120.21570.37620.032*
H2B0.63920.19020.47370.032*
C30.5668 (3)0.3514 (3)0.4601 (2)0.0333 (9)
H3A0.62940.39360.45130.043*
H3B0.50660.38590.42090.043*
C40.4636 (3)0.3081 (3)0.5611 (2)0.0305 (8)
H4A0.40280.34270.52280.04*
H4B0.45580.32020.62180.04*
C50.4676 (3)0.1783 (3)0.5430 (2)0.0231 (7)
H5A0.52430.14170.58470.03*
H5B0.40180.14110.54960.03*
C60.2173 (2)−0.2175 (3)0.2675 (2)0.0186 (6)
C70.2634 (3)−0.4253 (3)0.2633 (2)0.0267 (8)
H7A0.3347−0.39490.27020.035*
H7B0.2445−0.46060.20490.035*
C80.2581 (3)−0.5172 (3)0.3318 (3)0.0291 (8)
H8A0.3−0.58550.32150.038*
H8B0.2881−0.48510.38960.038*
C90.0937 (3)−0.4574 (3)0.3478 (2)0.0243 (7)
H9A0.1245−0.42190.40420.032*
H9B0.0233−0.48440.3510.032*
C100.0878 (2)−0.3671 (3)0.2769 (2)0.0215 (7)
H10A0.0534−0.40080.22090.028*
H10B0.0466−0.29940.28980.028*
C110.1718 (2)0.1661 (3)0.1371 (2)0.0179 (6)
C120.1283 (3)0.2207 (3)−0.0155 (2)0.0251 (7)
H12A0.15360.1412−0.02450.033*
H12B0.17550.2776−0.03490.033*
C130.0202 (3)0.2361 (3)−0.0674 (2)0.0263 (7)
H13A0.02160.2282−0.12990.034*
H13B−0.0250.1742−0.05160.034*
C14−0.0276 (3)0.3579 (3)0.0376 (2)0.0256 (7)
H14A−0.07260.29530.05290.033*
H14B−0.0590.43380.04760.033*
C150.0785 (3)0.3487 (3)0.0951 (2)0.0243 (7)
H15A0.12190.41540.08390.032*
H15B0.0720.3510.15670.032*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Co10.0159 (2)0.0152 (2)0.0145 (2)−0.00138 (15)0.00206 (17)−0.00065 (15)
S10.0214 (4)0.0249 (4)0.0148 (4)−0.0058 (3)0.0039 (3)−0.0013 (3)
S20.0173 (4)0.0193 (4)0.0149 (4)−0.0030 (3)0.0032 (3)0.0000 (3)
S30.0166 (4)0.0175 (4)0.0203 (4)0.0001 (3)0.0032 (3)−0.0012 (3)
S40.0163 (4)0.0153 (4)0.0218 (4)0.0001 (3)0.0026 (3)0.0004 (3)
S50.0214 (4)0.0182 (4)0.0153 (4)0.0012 (3)0.0024 (3)−0.0020 (3)
S60.0236 (4)0.0159 (4)0.0152 (4)−0.0001 (3)0.0027 (3)−0.0018 (3)
N10.0189 (13)0.0256 (15)0.0168 (13)−0.0025 (11)0.0044 (10)−0.0021 (11)
N20.0187 (13)0.0153 (13)0.0299 (15)0.0016 (10)0.0023 (11)0.0022 (11)
N30.0326 (15)0.0181 (14)0.0151 (13)0.0033 (12)0.0031 (11)−0.0010 (11)
O10.0446 (16)0.0303 (14)0.0331 (14)−0.0102 (12)0.0056 (12)−0.0115 (11)
O20.0325 (13)0.0148 (11)0.0334 (13)−0.0013 (10)0.0011 (11)0.0023 (10)
O30.0423 (15)0.0227 (13)0.0207 (12)0.0092 (11)0.0016 (10)0.0036 (10)
C10.0196 (15)0.0152 (15)0.0169 (14)−0.0011 (12)0.0038 (12)0.0013 (11)
C20.0202 (16)0.0305 (19)0.0224 (16)−0.0080 (14)0.0027 (13)−0.0028 (14)
C30.039 (2)0.028 (2)0.0315 (19)−0.0114 (16)0.0025 (16)−0.0012 (15)
C40.0333 (19)0.0291 (19)0.0284 (18)0.0018 (15)0.0041 (15)−0.0087 (15)
C50.0224 (16)0.0314 (19)0.0155 (15)−0.0025 (14)0.0034 (12)−0.0023 (13)
C60.0178 (14)0.0214 (16)0.0153 (14)−0.0011 (12)−0.0001 (11)0.0002 (12)
C70.0234 (17)0.0186 (17)0.038 (2)0.0017 (13)0.0050 (15)−0.0023 (14)
C80.0283 (18)0.0166 (17)0.038 (2)0.0009 (13)−0.0057 (15)0.0010 (14)
C90.0294 (18)0.0181 (16)0.0246 (17)−0.0039 (13)0.0030 (14)0.0008 (13)
C100.0182 (15)0.0179 (16)0.0266 (17)−0.0031 (12)−0.0003 (13)0.0002 (13)
C110.0194 (15)0.0173 (15)0.0171 (15)−0.0051 (12)0.0038 (12)−0.0018 (12)
C120.0342 (19)0.0245 (17)0.0171 (16)0.0064 (14)0.0060 (13)0.0020 (13)
C130.0367 (19)0.0225 (17)0.0179 (16)0.0038 (14)0.0001 (14)0.0001 (13)
C140.0351 (19)0.0213 (17)0.0210 (16)0.0033 (14)0.0068 (14)0.0040 (13)
C150.0382 (19)0.0146 (16)0.0191 (16)0.0020 (14)0.0032 (14)−0.0008 (12)
Geometric parameters (Å, °) top
Co1—S22.2634 (8)C2—H2B0.99
Co1—S62.2663 (9)C3—H3A0.99
Co1—S42.2688 (9)C3—H3B0.99
Co1—S52.2702 (8)C4—C51.518 (5)
Co1—S32.2703 (9)C4—H4A0.99
Co1—S12.2790 (9)C4—H4B0.99
S1—C11.710 (3)C5—H5A0.99
S2—C11.726 (3)C5—H5B0.99
S3—C61.708 (3)C7—C81.519 (5)
S4—C61.715 (3)C7—H7A0.99
S5—C111.725 (3)C7—H7B0.99
S6—C111.713 (3)C8—H8A0.99
N1—C11.317 (4)C8—H8B0.99
N1—C51.465 (4)C9—C101.512 (5)
N1—C21.468 (4)C9—H9A0.99
N2—C61.329 (4)C9—H9B0.99
N2—C101.464 (4)C10—H10A0.99
N2—C71.468 (4)C10—H10B0.99
N3—C111.318 (4)C12—C131.513 (5)
N3—C121.465 (4)C12—H12A0.99
N3—C151.469 (4)C12—H12B0.99
O1—C31.415 (5)C13—H13A0.99
O1—C41.423 (5)C13—H13B0.99
O2—C91.420 (4)C14—C151.518 (5)
O2—C81.428 (4)C14—H14A0.99
O3—C141.430 (4)C14—H14B0.99
O3—C131.432 (4)C15—H15A0.99
C2—C31.516 (5)C15—H15B0.99
C2—H2A0.99
S2—Co1—S692.10 (3)N1—C5—H5B109.9
S2—Co1—S492.33 (3)C4—C5—H5B109.9
S6—Co1—S496.91 (3)H5A—C5—H5B108.3
S2—Co1—S5166.76 (4)N2—C6—S3124.9 (3)
S6—Co1—S576.55 (3)N2—C6—S4124.5 (3)
S4—Co1—S595.75 (3)S3—C6—S4110.5 (2)
S2—Co1—S397.76 (3)N2—C7—C8110.0 (3)
S6—Co1—S3168.36 (3)N2—C7—H7A109.7
S4—Co1—S376.61 (3)C8—C7—H7A109.7
S5—Co1—S394.31 (3)N2—C7—H7B109.7
S2—Co1—S176.77 (3)C8—C7—H7B109.7
S6—Co1—S194.22 (3)H7A—C7—H7B108.2
S4—Co1—S1164.70 (3)O2—C8—C7111.9 (3)
S5—Co1—S197.02 (3)O2—C8—H8A109.2
S3—Co1—S194.05 (3)C7—C8—H8A109.2
C1—S1—Co186.3 (1)O2—C8—H8B109.2
C1—S2—Co186.4 (1)C7—C8—H8B109.2
C6—S3—Co186.5 (1)H8A—C8—H8B107.9
C6—S4—Co186.4 (1)O2—C9—C10110.5 (3)
C11—S5—Co186.7 (1)O2—C9—H9A109.6
C11—S6—Co187.1 (1)C10—C9—H9A109.6
C1—N1—C5124.0 (3)O2—C9—H9B109.6
C1—N1—C2122.8 (3)C10—C9—H9B109.6
C5—N1—C2112.6 (3)H9A—C9—H9B108.1
C6—N2—C10122.2 (3)N2—C10—C9109.2 (3)
C6—N2—C7123.4 (3)N2—C10—H10A109.8
C10—N2—C7114.1 (3)C9—C10—H10A109.8
C11—N3—C12122.5 (3)N2—C10—H10B109.8
C11—N3—C15123.4 (3)C9—C10—H10B109.8
C12—N3—C15113.9 (3)H10A—C10—H10B108.3
C3—O1—C4110.6 (3)N3—C11—S6125.6 (3)
C9—O2—C8110.1 (3)N3—C11—S5124.8 (2)
C14—O3—C13109.6 (2)S6—C11—S5109.6 (2)
N1—C1—S1125.6 (2)N3—C12—C13109.2 (3)
N1—C1—S2124.1 (2)N3—C12—H12A109.8
S1—C1—S2110.33 (17)C13—C12—H12A109.8
N1—C2—C3108.9 (3)N3—C12—H12B109.8
N1—C2—H2A109.9C13—C12—H12B109.8
C3—C2—H2A109.9H12A—C12—H12B108.3
N1—C2—H2B109.9O3—C13—C12111.3 (3)
C3—C2—H2B109.9O3—C13—H13A109.4
H2A—C2—H2B108.3C12—C13—H13A109.4
O1—C3—C2111.2 (3)O3—C13—H13B109.4
O1—C3—H3A109.4C12—C13—H13B109.4
C2—C3—H3A109.4H13A—C13—H13B108
O1—C3—H3B109.4O3—C14—C15111.0 (3)
C2—C3—H3B109.4O3—C14—H14A109.4
H3A—C3—H3B108C15—C14—H14A109.4
O1—C4—C5111.3 (3)O3—C14—H14B109.4
O1—C4—H4A109.4C15—C14—H14B109.4
C5—C4—H4A109.4H14A—C14—H14B108
O1—C4—H4B109.4N3—C15—C14109.1 (3)
C5—C4—H4B109.4N3—C15—H15A109.9
H4A—C4—H4B108C14—C15—H15A109.9
N1—C5—C4109.0 (3)N3—C15—H15B109.9
N1—C5—H5A109.9C14—C15—H15B109.9
C4—C5—H5A109.9H15A—C15—H15B108.3
S2—Co1—S1—C1−3.29 (11)C5—N1—C2—C3−54.6 (4)
S6—Co1—S1—C187.88 (11)C4—O1—C3—C2−60.6 (4)
S4—Co1—S1—C1−48.75 (18)N1—C2—C3—O156.9 (4)
S5—Co1—S1—C1164.83 (11)C3—O1—C4—C560.2 (4)
S3—Co1—S1—C1−100.32 (11)C1—N1—C5—C4−117.1 (3)
S6—Co1—S2—C1−90.58 (11)C2—N1—C5—C454.2 (4)
S4—Co1—S2—C1172.41 (11)O1—C4—C5—N1−56.1 (4)
S5—Co1—S2—C1−59.94 (18)C10—N2—C6—S3−178.0 (2)
S3—Co1—S2—C195.61 (11)C7—N2—C6—S3−3.5 (5)
S1—Co1—S2—C13.26 (11)C10—N2—C6—S42.7 (5)
S2—Co1—S3—C689.61 (11)C7—N2—C6—S4177.2 (2)
S6—Co1—S3—C6−58.1 (2)Co1—S3—C6—N2−178.1 (3)
S4—Co1—S3—C6−0.94 (10)Co1—S3—C6—S41.30 (14)
S5—Co1—S3—C6−95.84 (11)Co1—S4—C6—N2178.1 (3)
S1—Co1—S3—C6166.79 (11)Co1—S4—C6—S3−1.30 (14)
S2—Co1—S4—C6−96.49 (11)C6—N2—C7—C8135.6 (3)
S6—Co1—S4—C6171.11 (10)C10—N2—C7—C8−49.5 (4)
S5—Co1—S4—C694.01 (11)C9—O2—C8—C7−60.1 (4)
S3—Co1—S4—C60.94 (10)N2—C7—C8—O252.4 (4)
S1—Co1—S4—C6−52.51 (17)C8—O2—C9—C1062.8 (3)
S2—Co1—S5—C11−30.55 (18)C6—N2—C10—C9−132.7 (3)
S6—Co1—S5—C111.03 (10)C7—N2—C10—C952.3 (4)
S4—Co1—S5—C1196.79 (11)O2—C9—C10—N2−58.1 (3)
S3—Co1—S5—C11173.73 (11)C12—N3—C11—S6176.3 (3)
S1—Co1—S5—C11−91.64 (11)C15—N3—C11—S61.2 (5)
S2—Co1—S6—C11172.07 (11)C12—N3—C11—S5−3.8 (5)
S4—Co1—S6—C11−95.33 (11)C15—N3—C11—S5−178.9 (3)
S5—Co1—S6—C11−1.04 (11)Co1—S6—C11—N3−178.7 (3)
S3—Co1—S6—C11−39.9 (2)Co1—S6—C11—S51.41 (14)
S1—Co1—S6—C1195.19 (11)Co1—S5—C11—N3178.7 (3)
C5—N1—C1—S1171.1 (3)Co1—S5—C11—S6−1.41 (14)
C2—N1—C1—S10.6 (5)C11—N3—C12—C13132.2 (3)
C5—N1—C1—S2−8.2 (5)C15—N3—C12—C13−52.3 (4)
C2—N1—C1—S2−178.7 (3)C14—O3—C13—C12−61.6 (4)
Co1—S1—C1—N1−174.9 (3)N3—C12—C13—O356.1 (4)
Co1—S1—C1—S24.48 (15)C13—O3—C14—C1561.6 (4)
Co1—S2—C1—N1174.9 (3)C11—N3—C15—C14−132.2 (3)
Co1—S2—C1—S1−4.51 (15)C12—N3—C15—C1452.3 (4)
C1—N1—C2—C3116.9 (3)O3—C14—C15—N3−56.1 (4)
references
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