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Acta Cryst. (2008). E64, m733-m734    [ doi:10.1107/S1600536808011598 ]

Tris[N-(2-furoyl)-N,N'-diphenylthioureato-[kappa]2O,S]cobalt(III)

H. Pérez, R. S. Corrêa, A. M. Plutín, B. O'Reilly and J. Duque

Abstract top

In the title compound, [Co(C18H13N2O2S)3], the CoIII atom is coordinated by the S and O atoms of three N-furoyl-N',N'-diphenylthiourea ligands in a slightly distorted octahedral geometry. The three O atoms are arranged fac, as are the three S atoms.

Comment top

Substituted N-acylthioureas are well known as chelating agents. Over recent years, many transition metal complexes with thiourea derivatives have been reported (Arslan et al., 2003), because this kind of ligands display a remarkably rich coordination chemistry.

In this paper, we report the crystal structure of the title compound (Fig. 1), which presents an octahedral environment about the CoIII atom with the ligands coordinating in a relatively distorted manner (Table 1). The Co—S bond lengths lie within the range of those found in the related structure (Jia et al., 2007; Pérez et al., 2008). The lengths of C—O, C—S and C—N bonds in the chelate rings are between characteristic single and double bond lengths; they are shorter than single bond and longer than double bond. These results can be explained by the existence of delocalization in the chelate rings. Fig. 2 shows the arrangement of the complex molecules in the unit cell.

Related literature top

For general background, see: Arslan et al. (2003). For related structures, see: Jia et al. (2007); Pérez et al. (2008). For the synthesis of the ligand, see: Hernández et al. (2003).

Experimental top

N-furoyl-N',N'-diphenylthiourea ligand was synthesized according to a procedure described by Hernández et al. (2003), by converting furoyl chloride into furoyl isothiocyanate and then condensing with an appropriate amine. To an ethanol solution (30 ml) containing the ligand (0.96 g, 3 mmol) was added an ethanol solution of Co(CH3COO)2.4H2O (0.25 g, 1 mmol). The solution was stirred at room temperature for 2 h, and at once a solution of NaOH (1 N) was added to adjust pH to the neutral value. The mixture was filtered and the filtrate was evaporated under reduced pressure to give a green solid, which was washed with acetone. Single crystals were obtained by slow evaporation of a chloroform/N,N-diphenylformamide solution (1:1, v/v) of the complex.

Refinement top

H atoms were positioned geometrically and refined as riding atoms, with C—H = 0.93 Å and Uiso(H) = 1.2Ueq(C).

Computing details top

Data collection: COLLECT (Nonius, 1998); cell refinement: DENZO/SCALEPACK (Otwinowski & Minor, 1997); data reduction: DENZO/SCALEPACK; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 (Farrugia, 1997); software used to prepare material for publication: WinGX (Farrugia, 1999).

Figures top
[Figure 1] Fig. 1. The molecular structure of the title compound. Displacement ellipsoids are drawn at the 50% probability level.
[Figure 2] Fig. 2. View of the unit cell of the title complex.
Tris[N-(2-furoyl)-N,N'-diphenylthioureato-κ2O,S]cobalt(III) top
Crystal data top
[Co(C18H13N2O2S)3]Z = 2
Mr = 1023.05F000 = 1056
Triclinic, P1Dx = 1.432 Mg m−3
Hall symbol: -P 1Mo Kα radiation
λ = 0.71073 Å
a = 10.0236 (11) ÅCell parameters from 8767 reflections
b = 13.1438 (16) Åθ = 2.9–25.4º
c = 19.388 (3) ŵ = 0.55 mm−1
α = 79.357 (7)ºT = 150 (2) K
β = 83.477 (8)ºBlock, green
γ = 71.152 (8)º0.15 × 0.13 × 0.02 mm
V = 2371.8 (5) Å3
Data collection top
Nonius KappaCCD
diffractometer		4680 reflections with I > 2σ(I)
T = 150(2) KRint = 0.092
φ and ω scansθmax = 25º
Absorption correction: Gaussian
(Coppens et al., 1965)		θmin = 3.0º
Tmin = 0.955, Tmax = 0.980h = −11→11
13609 measured reflectionsk = −15→14
8289 independent reflectionsl = −23→23
Refinement top
Refinement on F2H-atom parameters constrained
Least-squares matrix: full  w = 1/[σ2(Fo2) + (0.069P)2 + 0.4724P]
where P = (Fo2 + 2Fc2)/3
R[F2 > 2σ(F2)] = 0.086(Δ/σ)max < 0.001
wR(F2) = 0.222Δρmax = 0.51 e Å−3
S = 1.19Δρmin = −0.53 e Å−3
8289 reflectionsExtinction correction: SHELXL97 (Sheldrick, 2008), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
632 parametersExtinction coefficient: 0.0076 (14)
Crystal data top
[Co(C18H13N2O2S)3]γ = 71.152 (8)º
Mr = 1023.05V = 2371.8 (5) Å3
Triclinic, P1Z = 2
a = 10.0236 (11) ÅMo Kα
b = 13.1438 (16) ŵ = 0.55 mm−1
c = 19.388 (3) ÅT = 150 (2) K
α = 79.357 (7)º0.15 × 0.13 × 0.02 mm
β = 83.477 (8)º
Data collection top
Nonius KappaCCD
diffractometer		8289 independent reflections
Absorption correction: Gaussian
(Coppens et al., 1965)		4680 reflections with I > 2σ(I)
Tmin = 0.955, Tmax = 0.980Rint = 0.092
13609 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.086632 parameters
wR(F2) = 0.222H-atom parameters constrained
S = 1.19Δρmax = 0.51 e Å−3
8289 reflectionsΔρmin = −0.53 e Å−3
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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
C10.8134 (7)0.8428 (6)0.3061 (3)0.0522 (17)
C20.6159 (7)0.8246 (6)0.2602 (4)0.0555 (18)
C30.8605 (7)0.9270 (6)0.3268 (4)0.0588 (19)
C40.7991 (8)1.0351 (6)0.3228 (4)0.066 (2)
H40.71021.07480.30680.079*
C50.8942 (10)1.0766 (8)0.3472 (5)0.089 (3)
H50.87981.1490.35080.106*
C61.0102 (10)0.9925 (8)0.3645 (5)0.087 (3)
H61.09030.99760.38180.104*
C70.4392 (7)1.0014 (5)0.2305 (4)0.0562 (19)
C80.3801 (7)1.0434 (6)0.2904 (5)0.068 (2)
H80.37780.99730.33280.082*
C90.3241 (8)1.1545 (7)0.2874 (5)0.073 (2)
H90.28381.18360.32790.087*
C100.3278 (9)1.2218 (7)0.2253 (6)0.082 (3)
H100.28931.29690.2230.099*
C110.3895 (9)1.1776 (7)0.1656 (5)0.076 (2)
H110.39281.22350.12310.091*
C120.4462 (8)1.0663 (6)0.1680 (4)0.062 (2)
H120.4881.03670.12780.075*
C130.4055 (7)0.8386 (5)0.1994 (4)0.0556 (18)
C140.2771 (7)0.8351 (6)0.2318 (4)0.064 (2)
H140.25090.85560.27610.076*
C150.1880 (8)0.8017 (7)0.1994 (5)0.077 (2)
H150.10240.79740.22180.093*
C160.2263 (8)0.7744 (6)0.1329 (5)0.073 (2)
H160.16590.75290.10990.087*
C170.3530 (8)0.7791 (6)0.1013 (4)0.067 (2)
H170.37860.76030.05660.08*
C180.4443 (7)0.8113 (6)0.1343 (4)0.0613 (19)
H180.53070.81410.11230.074*
C190.8633 (7)0.7096 (5)0.1301 (4)0.0530 (17)
C200.8537 (6)0.5288 (5)0.1438 (4)0.0521 (17)
C210.8372 (7)0.8086 (5)0.0784 (4)0.0529 (17)
C220.7907 (8)0.8320 (6)0.0137 (4)0.064 (2)
H220.76670.7857−0.01010.077*
C230.7852 (9)0.9420 (6)−0.0116 (5)0.076 (2)
H230.75610.9819−0.05510.091*
C240.8294 (8)0.9762 (7)0.0388 (4)0.070 (2)
H240.83791.04540.03550.084*
C250.7778 (7)0.4928 (6)0.0372 (4)0.0527 (17)
C260.6395 (7)0.5639 (6)0.0319 (4)0.065 (2)
H260.5880.59220.07080.078*
C270.5821 (8)0.5905 (7)−0.0333 (4)0.066 (2)
H270.49050.6376−0.0380.079*
C280.6569 (8)0.5492 (6)−0.0910 (4)0.067 (2)
H280.61690.5683−0.13440.081*
C290.7912 (7)0.4796 (6)−0.0840 (4)0.0608 (19)
H290.8420.4503−0.12270.073*
C300.8521 (7)0.4524 (6)−0.0202 (4)0.0576 (18)
H300.94430.4062−0.01630.069*
C310.8687 (7)0.3430 (5)0.1307 (4)0.0546 (18)
C320.7627 (8)0.2952 (6)0.1373 (4)0.0598 (19)
H320.670.33820.12980.072*
C330.7944 (8)0.1840 (6)0.1550 (4)0.069 (2)
H330.72310.15210.15810.083*
C340.9307 (9)0.1195 (6)0.1682 (4)0.068 (2)
H340.95130.04450.18060.081*
C351.0364 (8)0.1675 (6)0.1628 (4)0.067 (2)
H351.12830.12480.17240.081*
C361.0056 (7)0.2786 (6)0.1432 (4)0.0593 (19)
H361.07750.31030.13830.071*
C371.1649 (7)0.4839 (6)0.3130 (4)0.0509 (17)
C381.0025 (7)0.4247 (6)0.3945 (4)0.0541 (18)
C391.3184 (7)0.4579 (6)0.2980 (4)0.0518 (17)
C401.4255 (8)0.3729 (6)0.3245 (4)0.0600 (19)
H401.42020.31390.35820.072*
C411.5501 (8)0.3934 (8)0.2891 (5)0.080 (3)
H411.64260.34890.29530.096*
C421.5094 (8)0.4877 (8)0.2457 (5)0.077 (3)
H421.570.520.21680.093*
C430.8608 (7)0.3438 (6)0.4858 (4)0.0571 (18)
C440.8498 (8)0.3463 (6)0.5573 (4)0.062 (2)
H440.92560.34840.57990.075*
C450.7243 (9)0.3454 (6)0.5943 (4)0.070 (2)
H450.71620.34630.64250.084*
C460.6115 (9)0.3433 (7)0.5617 (5)0.080 (2)
H460.52710.3440.58730.096*
C470.6237 (9)0.3400 (8)0.4914 (5)0.088 (3)
H470.5470.33830.46930.105*
C480.7462 (8)0.3392 (7)0.4529 (4)0.079 (2)
H480.75370.33550.40510.095*
C491.1159 (7)0.2534 (6)0.4715 (4)0.0565 (18)
C501.2270 (8)0.2720 (7)0.4956 (4)0.069 (2)
H501.22860.34280.4940.083*
C511.3385 (9)0.1833 (9)0.5227 (5)0.087 (3)
H511.41460.19480.53980.104*
C521.3359 (11)0.0805 (9)0.5241 (5)0.099 (3)
H521.41030.02220.54290.119*
C531.2261 (12)0.0598 (8)0.4984 (5)0.099 (3)
H531.2264−0.01110.49850.119*
C541.1151 (9)0.1486 (7)0.4724 (4)0.074 (2)
H541.0390.13720.45530.088*
N10.6891 (6)0.8853 (5)0.2768 (3)0.0576 (15)
N20.4907 (5)0.8844 (4)0.2321 (3)0.0546 (15)
N30.8304 (5)0.6293 (4)0.1078 (3)0.0515 (14)
N40.8344 (6)0.4568 (4)0.1060 (3)0.0549 (15)
N51.1304 (6)0.4083 (5)0.3616 (3)0.0549 (15)
N60.9923 (5)0.3427 (5)0.4472 (3)0.0543 (15)
O10.8953 (4)0.7458 (4)0.3172 (2)0.0539 (12)
O20.9919 (5)0.8962 (4)0.3525 (3)0.0744 (15)
O30.9116 (4)0.7098 (4)0.1875 (2)0.0517 (11)
O40.8609 (5)0.8976 (4)0.0959 (3)0.0662 (14)
O51.0897 (4)0.5727 (4)0.2805 (2)0.0533 (12)
O61.3660 (5)0.5297 (4)0.2500 (3)0.0701 (14)
S10.65537 (17)0.68586 (14)0.27060 (10)0.0546 (5)
S20.89274 (18)0.48093 (14)0.22979 (10)0.0528 (5)
S30.85482 (18)0.53514 (16)0.38161 (10)0.0602 (5)
Co10.88802 (9)0.62353 (7)0.27666 (5)0.0511 (3)
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
C10.050 (4)0.064 (5)0.046 (4)−0.018 (4)−0.008 (3)−0.015 (4)
C20.049 (4)0.056 (4)0.060 (5)−0.010 (3)−0.011 (3)−0.011 (4)
C30.051 (4)0.072 (5)0.058 (5)−0.019 (4)−0.013 (4)−0.015 (4)
C40.064 (5)0.060 (5)0.080 (6)−0.017 (4)−0.013 (4)−0.022 (4)
C50.101 (7)0.073 (6)0.108 (8)−0.034 (5)−0.016 (6)−0.033 (5)
C60.087 (6)0.095 (7)0.105 (7)−0.046 (6)−0.010 (5)−0.046 (6)
C70.053 (4)0.042 (4)0.075 (5)−0.007 (3)−0.018 (4)−0.017 (4)
C80.062 (5)0.065 (5)0.077 (6)−0.011 (4)−0.009 (4)−0.021 (4)
C90.070 (5)0.066 (5)0.088 (7)−0.019 (4)0.002 (5)−0.033 (5)
C100.081 (6)0.057 (5)0.114 (8)−0.014 (4)−0.036 (6)−0.025 (6)
C110.088 (6)0.058 (5)0.086 (7)−0.024 (4)−0.026 (5)−0.006 (5)
C120.073 (5)0.048 (4)0.070 (5)−0.018 (4)−0.019 (4)−0.010 (4)
C130.049 (4)0.047 (4)0.068 (5)−0.009 (3)−0.013 (4)−0.008 (4)
C140.056 (4)0.065 (5)0.075 (6)−0.024 (4)0.001 (4)−0.017 (4)
C150.055 (5)0.068 (5)0.115 (8)−0.022 (4)−0.012 (5)−0.018 (5)
C160.058 (5)0.046 (4)0.118 (8)−0.010 (3)−0.030 (5)−0.016 (5)
C170.065 (5)0.060 (5)0.073 (6)−0.006 (4)−0.022 (4)−0.016 (4)
C180.050 (4)0.069 (5)0.069 (5)−0.014 (3)−0.007 (4)−0.026 (4)
C190.048 (4)0.051 (4)0.058 (5)−0.013 (3)−0.005 (3)−0.007 (4)
C200.044 (4)0.047 (4)0.067 (5)−0.017 (3)−0.003 (3)−0.009 (4)
C210.054 (4)0.050 (4)0.058 (5)−0.019 (3)−0.007 (3)−0.009 (3)
C220.075 (5)0.056 (5)0.063 (5)−0.018 (4)−0.022 (4)−0.008 (4)
C230.092 (6)0.058 (5)0.069 (6)−0.011 (4)−0.022 (5)0.001 (4)
C240.088 (6)0.059 (5)0.063 (5)−0.024 (4)−0.007 (4)−0.003 (4)
C250.058 (4)0.054 (4)0.052 (4)−0.019 (3)−0.014 (3)−0.011 (3)
C260.054 (4)0.074 (5)0.066 (5)−0.013 (4)−0.011 (4)−0.018 (4)
C270.053 (4)0.083 (6)0.060 (5)−0.012 (4)−0.010 (4)−0.020 (4)
C280.071 (5)0.073 (5)0.065 (5)−0.030 (4)−0.014 (4)−0.010 (4)
C290.060 (4)0.062 (5)0.063 (5)−0.016 (4)−0.002 (4)−0.024 (4)
C300.053 (4)0.068 (5)0.054 (5)−0.016 (3)−0.007 (4)−0.020 (4)
C310.063 (4)0.048 (4)0.057 (5)−0.016 (3)−0.013 (4)−0.013 (3)
C320.056 (4)0.058 (5)0.071 (5)−0.022 (4)−0.013 (4)−0.013 (4)
C330.075 (5)0.067 (5)0.072 (6)−0.029 (4)−0.007 (4)−0.014 (4)
C340.081 (5)0.049 (4)0.075 (6)−0.019 (4)−0.007 (4)−0.016 (4)
C350.062 (5)0.050 (4)0.079 (6)−0.001 (4)−0.017 (4)−0.006 (4)
C360.057 (4)0.052 (4)0.067 (5)−0.011 (3)−0.012 (4)−0.008 (4)
C370.047 (4)0.058 (4)0.055 (4)−0.022 (3)−0.003 (3)−0.018 (4)
C380.043 (4)0.064 (5)0.059 (5)−0.018 (3)−0.008 (3)−0.015 (4)
C390.057 (4)0.054 (4)0.047 (4)−0.020 (3)0.003 (3)−0.012 (3)
C400.062 (5)0.058 (5)0.060 (5)−0.014 (4)−0.019 (4)−0.008 (4)
C410.043 (4)0.100 (7)0.098 (7)−0.004 (4)−0.019 (5)−0.037 (6)
C420.044 (4)0.113 (7)0.089 (7)−0.027 (5)0.005 (4)−0.052 (6)
C430.054 (4)0.065 (5)0.054 (5)−0.025 (3)0.002 (4)−0.007 (4)
C440.063 (5)0.073 (5)0.055 (5)−0.027 (4)0.005 (4)−0.013 (4)
C450.089 (6)0.078 (5)0.051 (5)−0.033 (5)0.008 (4)−0.025 (4)
C460.066 (5)0.100 (7)0.081 (7)−0.034 (5)0.006 (5)−0.021 (5)
C470.059 (5)0.136 (9)0.084 (7)−0.050 (5)0.001 (5)−0.022 (6)
C480.069 (5)0.116 (7)0.070 (6)−0.043 (5)−0.012 (4)−0.029 (5)
C490.057 (4)0.051 (4)0.061 (5)−0.014 (3)−0.007 (4)−0.011 (4)
C500.065 (5)0.069 (5)0.070 (5)−0.012 (4)−0.011 (4)−0.012 (4)
C510.061 (5)0.103 (8)0.080 (6)−0.008 (5)−0.022 (4)0.004 (6)
C520.079 (7)0.090 (8)0.091 (8)0.010 (6)0.010 (6)0.004 (6)
C530.114 (8)0.066 (6)0.090 (7)0.006 (6)0.000 (6)−0.008 (5)
C540.082 (6)0.070 (5)0.070 (6)−0.022 (5)−0.005 (4)−0.015 (4)
N10.046 (3)0.058 (4)0.071 (4)−0.012 (3)−0.014 (3)−0.015 (3)
N20.042 (3)0.056 (4)0.072 (4)−0.016 (3)−0.015 (3)−0.017 (3)
N30.052 (3)0.048 (3)0.059 (4)−0.016 (3)−0.012 (3)−0.013 (3)
N40.060 (3)0.046 (3)0.062 (4)−0.018 (3)−0.011 (3)−0.008 (3)
N50.054 (3)0.054 (3)0.057 (4)−0.017 (3)−0.009 (3)−0.008 (3)
N60.048 (3)0.059 (4)0.057 (4)−0.017 (3)−0.008 (3)−0.005 (3)
O10.045 (2)0.057 (3)0.061 (3)−0.011 (2)−0.012 (2)−0.016 (2)
O20.062 (3)0.082 (4)0.089 (4)−0.021 (3)−0.010 (3)−0.038 (3)
O30.045 (2)0.058 (3)0.055 (3)−0.015 (2)−0.009 (2)−0.014 (2)
O40.073 (3)0.058 (3)0.072 (4)−0.024 (3)−0.012 (3)−0.010 (3)
O50.051 (3)0.056 (3)0.054 (3)−0.013 (2)−0.010 (2)−0.011 (2)
O60.059 (3)0.081 (4)0.077 (4)−0.026 (3)0.000 (3)−0.023 (3)
S10.0444 (9)0.0532 (10)0.0670 (12)−0.0134 (8)−0.0088 (8)−0.0113 (9)
S20.0522 (10)0.0526 (10)0.0546 (11)−0.0147 (8)−0.0077 (8)−0.0111 (8)
S30.0510 (10)0.0651 (12)0.0587 (12)−0.0097 (9)−0.0024 (9)−0.0108 (9)
Co10.0441 (5)0.0536 (6)0.0563 (6)−0.0120 (4)−0.0081 (4)−0.0130 (5)
Geometric parameters (Å, °) top
C1—O11.268 (8)C28—H280.93
C1—N11.335 (8)C29—C301.378 (9)
C1—C31.468 (10)C29—H290.93
C2—N11.343 (8)C30—H300.93
C2—N21.361 (8)C31—C361.381 (9)
C2—S11.714 (7)C31—C321.383 (9)
C3—C41.344 (10)C31—N41.423 (8)
C3—O21.371 (8)C32—C331.376 (10)
C4—C51.402 (11)C32—H320.93
C4—H40.93C33—C341.379 (10)
C5—C61.344 (12)C33—H330.93
C5—H50.93C34—C351.383 (10)
C6—O21.400 (9)C34—H340.93
C6—H60.93C35—C361.379 (9)
C7—C121.356 (10)C35—H350.93
C7—C81.370 (10)C36—H360.93
C7—N21.451 (8)C37—O51.263 (7)
C8—C91.378 (10)C37—N51.340 (8)
C8—H80.93C37—C391.470 (9)
C9—C101.361 (11)C38—N51.335 (8)
C9—H90.93C38—N61.362 (8)
C10—C111.384 (12)C38—S31.710 (7)
C10—H100.93C39—C401.342 (9)
C11—C121.382 (10)C39—O61.361 (8)
C11—H110.93C40—C411.434 (11)
C12—H120.93C40—H400.93
C13—C181.356 (10)C41—C421.333 (11)
C13—C141.377 (9)C41—H410.93
C13—N21.445 (8)C42—O61.362 (8)
C14—C151.368 (10)C42—H420.93
C14—H140.93C43—C441.383 (10)
C15—C161.380 (12)C43—C481.399 (9)
C15—H150.93C43—N61.437 (8)
C16—C171.361 (11)C44—C451.378 (10)
C16—H160.93C44—H440.93
C17—C181.382 (10)C45—C461.367 (10)
C17—H170.93C45—H450.93
C18—H180.93C46—C471.362 (11)
C19—O31.263 (8)C46—H460.93
C19—N31.355 (9)C47—C481.361 (11)
C19—C211.458 (9)C47—H470.93
C20—N31.336 (8)C48—H480.93
C20—N41.370 (8)C49—C501.362 (10)
C20—S21.712 (7)C49—C541.376 (10)
C21—C221.336 (9)C49—N61.458 (8)
C21—O41.371 (8)C50—C511.397 (10)
C22—C231.423 (10)C50—H500.93
C22—H220.93C51—C521.356 (13)
C23—C241.320 (11)C51—H510.93
C23—H230.93C52—C531.379 (14)
C24—O41.356 (8)C52—H520.93
C24—H240.93C53—C541.388 (14)
C25—C301.360 (9)C53—H530.93
C25—C261.402 (9)C54—H540.93
C25—N41.444 (8)O1—Co11.939 (5)
C26—C271.387 (9)O3—Co11.920 (5)
C26—H260.93O5—Co11.919 (4)
C27—C281.372 (10)S1—Co12.217 (2)
C27—H270.93S2—Co12.214 (2)
C28—C291.366 (10)S3—Co12.196 (2)
O1—C1—N1131.6 (7)C33—C34—C35119.3 (7)
O1—C1—C3116.8 (6)C33—C34—H34120.3
N1—C1—C3111.5 (6)C35—C34—H34120.3
N1—C2—N2113.6 (6)C36—C35—C34120.1 (7)
N1—C2—S1130.0 (5)C36—C35—H35120
N2—C2—S1116.5 (5)C34—C35—H35120
C4—C3—O2110.6 (7)C35—C36—C31120.4 (7)
C4—C3—C1131.4 (7)C35—C36—H36119.8
O2—C3—C1117.9 (6)C31—C36—H36119.8
C3—C4—C5107.1 (7)O5—C37—N5131.3 (6)
C3—C4—H4126.4O5—C37—C39116.2 (6)
C5—C4—H4126.4N5—C37—C39112.4 (6)
C6—C5—C4107.5 (8)N5—C38—N6114.3 (6)
C6—C5—H5126.3N5—C38—S3129.0 (6)
C4—C5—H5126.3N6—C38—S3116.7 (5)
C5—C6—O2109.5 (7)C40—C39—O6111.4 (6)
C5—C6—H6125.2C40—C39—C37130.9 (7)
O2—C6—H6125.2O6—C39—C37117.6 (6)
C12—C7—C8121.8 (7)C39—C40—C41104.7 (7)
C12—C7—N2118.2 (7)C39—C40—H40127.6
C8—C7—N2120.0 (7)C41—C40—H40127.6
C7—C8—C9119.5 (8)C42—C41—C40107.6 (7)
C7—C8—H8120.2C42—C41—H41126.2
C9—C8—H8120.2C40—C41—H41126.2
C10—C9—C8120.1 (9)C41—C42—O6110.0 (8)
C10—C9—H9119.9C41—C42—H42125
C8—C9—H9119.9O6—C42—H42125
C9—C10—C11119.3 (8)C44—C43—C48119.8 (7)
C9—C10—H10120.3C44—C43—N6118.9 (6)
C11—C10—H10120.3C48—C43—N6121.3 (7)
C12—C11—C10121.0 (8)C45—C44—C43118.7 (7)
C12—C11—H11119.5C45—C44—H44120.6
C10—C11—H11119.5C43—C44—H44120.6
C7—C12—C11118.2 (8)C46—C45—C44121.3 (8)
C7—C12—H12120.9C46—C45—H45119.3
C11—C12—H12120.9C44—C45—H45119.3
C18—C13—C14120.7 (7)C47—C46—C45119.5 (8)
C18—C13—N2120.1 (7)C47—C46—H46120.2
C14—C13—N2118.8 (7)C45—C46—H46120.2
C15—C14—C13120.4 (8)C48—C47—C46121.2 (8)
C15—C14—H14119.8C48—C47—H47119.4
C13—C14—H14119.8C46—C47—H47119.4
C14—C15—C16119.2 (8)C47—C48—C43119.4 (8)
C14—C15—H15120.4C47—C48—H48120.3
C16—C15—H15120.4C43—C48—H48120.3
C17—C16—C15119.7 (8)C50—C49—C54120.5 (7)
C17—C16—H16120.1C50—C49—N6121.4 (7)
C15—C16—H16120.1C54—C49—N6118.1 (7)
C16—C17—C18121.2 (8)C49—C50—C51119.0 (8)
C16—C17—H17119.4C49—C50—H50120.5
C18—C17—H17119.4C51—C50—H50120.5
C13—C18—C17118.7 (7)C52—C51—C50120.0 (9)
C13—C18—H18120.6C52—C51—H51120
C17—C18—H18120.6C50—C51—H51120
O3—C19—N3129.7 (6)C51—C52—C53121.9 (9)
O3—C19—C21117.7 (6)C51—C52—H52119.1
N3—C19—C21112.6 (6)C53—C52—H52119.1
N3—C20—N4113.4 (6)C52—C53—C54117.5 (10)
N3—C20—S2129.6 (6)C52—C53—H53121.2
N4—C20—S2116.8 (5)C54—C53—H53121.2
C22—C21—O4110.2 (6)C49—C54—C53121.1 (9)
C22—C21—C19131.5 (7)C49—C54—H54119.5
O4—C21—C19118.3 (6)C53—C54—H54119.5
C21—C22—C23106.3 (7)C1—N1—C2123.2 (6)
C21—C22—H22126.9C2—N2—C13123.4 (6)
C23—C22—H22126.9C2—N2—C7120.3 (5)
C24—C23—C22106.6 (7)C13—N2—C7116.2 (5)
C24—C23—H23126.7C20—N3—C19123.9 (6)
C22—C23—H23126.7C20—N4—C31123.1 (6)
C23—C24—O4111.3 (7)C20—N4—C25121.3 (5)
C23—C24—H24124.4C31—N4—C25115.6 (6)
O4—C24—H24124.4C38—N5—C37123.1 (6)
C30—C25—C26120.5 (6)C38—N6—C43121.9 (6)
C30—C25—N4121.1 (6)C38—N6—C49121.9 (6)
C26—C25—N4118.3 (7)C43—N6—C49116.0 (6)
C27—C26—C25117.8 (7)C1—O1—Co1126.7 (4)
C27—C26—H26121.1C3—O2—C6105.2 (6)
C25—C26—H26121.1C19—O3—Co1127.0 (4)
C28—C27—C26121.7 (7)C24—O4—C21105.7 (6)
C28—C27—H27119.2C37—O5—Co1127.7 (4)
C26—C27—H27119.2C39—O6—C42106.3 (6)
C29—C28—C27119.1 (7)C2—S1—Co1104.5 (2)
C29—C28—H28120.4C20—S2—Co1106.4 (2)
C27—C28—H28120.4C38—S3—Co1106.0 (3)
C28—C29—C30120.8 (7)O5—Co1—O388.20 (19)
C28—C29—H29119.6O5—Co1—O185.77 (19)
C30—C29—H29119.6O3—Co1—O185.5 (2)
C25—C30—C29120.2 (7)O5—Co1—S393.19 (15)
C25—C30—H30119.9O3—Co1—S3176.11 (15)
C29—C30—H30119.9O1—Co1—S390.95 (15)
C36—C31—C32119.5 (6)O5—Co1—S291.05 (15)
C36—C31—N4121.9 (6)O3—Co1—S293.98 (15)
C32—C31—N4118.4 (6)O1—Co1—S2176.80 (14)
C33—C32—C31120.0 (7)S3—Co1—S289.62 (8)
C33—C32—H32120O5—Co1—S1178.62 (16)
C31—C32—H32120O3—Co1—S190.58 (13)
C32—C33—C34120.7 (7)O1—Co1—S193.51 (14)
C32—C33—H33119.6S3—Co1—S187.99 (7)
C34—C33—H33119.6S2—Co1—S189.66 (7)
O1—C1—C3—C4−179.4 (8)C14—C13—N2—C7−70.9 (8)
N1—C1—C3—C41.9 (12)C12—C7—N2—C2105.8 (8)
O1—C1—C3—O23.8 (10)C8—C7—N2—C2−76.9 (9)
N1—C1—C3—O2−174.9 (6)C12—C7—N2—C13−71.2 (8)
O2—C3—C4—C5−0.3 (10)C8—C7—N2—C13106.1 (8)
C1—C3—C4—C5−177.3 (8)N4—C20—N3—C19−169.6 (6)
C3—C4—C5—C60.6 (11)S2—C20—N3—C1914.7 (10)
C4—C5—C6—O2−0.6 (11)O3—C19—N3—C20−4.5 (11)
C12—C7—C8—C91.0 (11)C21—C19—N3—C20175.4 (6)
N2—C7—C8—C9−176.2 (6)N3—C20—N4—C31172.6 (6)
C7—C8—C9—C10−0.1 (12)S2—C20—N4—C31−11.1 (9)
C8—C9—C10—C11−0.6 (12)N3—C20—N4—C25−7.0 (9)
C9—C10—C11—C120.5 (12)S2—C20—N4—C25169.3 (5)
C8—C7—C12—C11−1.1 (11)C36—C31—N4—C20−63.5 (10)
N2—C7—C12—C11176.2 (6)C32—C31—N4—C20121.4 (7)
C10—C11—C12—C70.3 (12)C36—C31—N4—C25116.1 (7)
C18—C13—C14—C151.4 (11)C32—C31—N4—C25−59.0 (9)
N2—C13—C14—C15173.9 (6)C30—C25—N4—C20121.4 (8)
C13—C14—C15—C16−1.8 (11)C26—C25—N4—C20−63.8 (9)
C14—C15—C16—C171.2 (11)C30—C25—N4—C31−58.2 (9)
C15—C16—C17—C18−0.3 (11)C26—C25—N4—C31116.6 (7)
C14—C13—C18—C17−0.5 (11)N6—C38—N5—C37−173.5 (6)
N2—C13—C18—C17−172.9 (6)S3—C38—N5—C373.9 (11)
C16—C17—C18—C13−0.1 (11)O5—C37—N5—C38−12.4 (12)
O3—C19—C21—C22178.2 (8)C39—C37—N5—C38165.3 (6)
N3—C19—C21—C22−1.8 (11)N5—C38—N6—C43−176.6 (6)
O3—C19—C21—O4−2.7 (9)S3—C38—N6—C435.7 (9)
N3—C19—C21—O4177.4 (6)N5—C38—N6—C498.5 (10)
O4—C21—C22—C230.3 (9)S3—C38—N6—C49−169.2 (5)
C19—C21—C22—C23179.5 (7)C44—C43—N6—C38−117.6 (8)
C21—C22—C23—C240.6 (9)C48—C43—N6—C3864.3 (10)
C22—C23—C24—O4−1.2 (10)C44—C43—N6—C4957.6 (9)
C30—C25—C26—C270.2 (11)C48—C43—N6—C49−120.5 (8)
N4—C25—C26—C27−174.6 (7)C50—C49—N6—C3857.1 (10)
C25—C26—C27—C280.1 (12)C54—C49—N6—C38−125.7 (8)
C26—C27—C28—C290.4 (12)C50—C49—N6—C43−118.1 (8)
C27—C28—C29—C30−1.1 (12)C54—C49—N6—C4359.1 (9)
C26—C25—C30—C29−1.0 (11)N1—C1—O1—Co114.3 (11)
N4—C25—C30—C29173.7 (6)C3—C1—O1—Co1−164.0 (5)
C28—C29—C30—C251.4 (11)C4—C3—O2—C6−0.1 (9)
C36—C31—C32—C33−1.1 (11)C1—C3—O2—C6177.4 (7)
N4—C31—C32—C33174.2 (7)C5—C6—O2—C30.5 (10)
C31—C32—C33—C341.8 (12)N3—C19—O3—Co1−26.9 (10)
C32—C33—C34—C35−0.7 (12)C21—C19—O3—Co1153.2 (5)
C33—C34—C35—C36−1.1 (12)C23—C24—O4—C211.4 (9)
C34—C35—C36—C311.8 (12)C22—C21—O4—C24−1.0 (8)
C32—C31—C36—C35−0.7 (11)C19—C21—O4—C24179.6 (6)
N4—C31—C36—C35−175.8 (7)N5—C37—O5—Co1−11.8 (11)
O5—C37—C39—C40178.2 (7)C39—C37—O5—Co1170.6 (4)
N5—C37—C39—C400.1 (11)C40—C39—O6—C420.4 (8)
O5—C37—C39—O6−1.3 (9)C37—C39—O6—C42179.9 (6)
N5—C37—C39—O6−179.3 (6)C41—C42—O6—C390.2 (9)
O6—C39—C40—C41−0.7 (9)N1—C2—S1—Co1−22.5 (8)
C37—C39—C40—C41179.8 (7)N2—C2—S1—Co1158.8 (5)
C39—C40—C41—C420.8 (9)N3—C20—S2—Co12.9 (7)
C40—C41—C42—O6−0.6 (10)N4—C20—S2—Co1−172.7 (4)
C48—C43—C44—C45−0.8 (11)N5—C38—S3—Co119.4 (7)
N6—C43—C44—C45−178.9 (7)N6—C38—S3—Co1−163.3 (5)
C43—C44—C45—C46−0.6 (12)C37—O5—Co1—O3−153.8 (6)
C44—C45—C46—C471.1 (14)C37—O5—Co1—O1120.6 (6)
C45—C46—C47—C48−0.2 (15)C37—O5—Co1—S329.9 (5)
C46—C47—C48—C43−1.2 (14)C37—O5—Co1—S2−59.8 (5)
C44—C43—C48—C471.7 (13)C19—O3—Co1—O5125.6 (5)
N6—C43—C48—C47179.8 (7)C19—O3—Co1—O1−148.5 (5)
C54—C49—C50—C51−1.5 (12)C19—O3—Co1—S234.7 (5)
N6—C49—C50—C51175.6 (7)C19—O3—Co1—S1−55.0 (5)
C49—C50—C51—C520.7 (13)C1—O1—Co1—O5147.3 (6)
C50—C51—C52—C530.9 (15)C1—O1—Co1—O358.8 (6)
C51—C52—C53—C54−1.6 (15)C1—O1—Co1—S3−119.6 (5)
C50—C49—C54—C530.7 (13)C1—O1—Co1—S1−31.6 (6)
N6—C49—C54—C53−176.5 (8)C38—S3—Co1—O5−27.9 (3)
C52—C53—C54—C490.8 (14)C38—S3—Co1—O1−113.7 (3)
O1—C1—N1—C28.9 (12)C38—S3—Co1—S263.1 (3)
C3—C1—N1—C2−172.6 (6)C38—S3—Co1—S1152.8 (3)
N2—C2—N1—C1178.9 (6)C20—S2—Co1—O5−108.4 (3)
S1—C2—N1—C10.1 (11)C20—S2—Co1—O3−20.2 (3)
N1—C2—N2—C13169.1 (6)C20—S2—Co1—S3158.4 (2)
S1—C2—N2—C13−11.9 (9)C20—S2—Co1—S170.4 (2)
N1—C2—N2—C7−7.6 (10)C2—S1—Co1—O3−56.2 (3)
S1—C2—N2—C7171.3 (5)C2—S1—Co1—O129.4 (3)
C18—C13—N2—C2−75.3 (9)C2—S1—Co1—S3120.2 (3)
C14—C13—N2—C2112.2 (8)C2—S1—Co1—S2−150.2 (3)
C18—C13—N2—C7101.6 (8)
Table 1
Selected geometric parameters (Å, °) top
O1—Co11.939 (5)S1—Co12.217 (2)
O3—Co11.920 (5)S2—Co12.214 (2)
O5—Co11.919 (4)S3—Co12.196 (2)
O5—Co1—O388.20 (19)O1—Co1—S2176.80 (14)
O5—Co1—O185.77 (19)S3—Co1—S289.62 (8)
O3—Co1—O185.5 (2)O5—Co1—S1178.62 (16)
O5—Co1—S393.19 (15)O3—Co1—S190.58 (13)
O3—Co1—S3176.11 (15)O1—Co1—S193.51 (14)
O1—Co1—S390.95 (15)S3—Co1—S187.99 (7)
O5—Co1—S291.05 (15)S2—Co1—S189.66 (7)
O3—Co1—S293.98 (15)
Acknowledgements top

The authors thank the Crystallography Group, São Carlos Physics Institute, USP, Brazil, for allowing the X-ray data collection. The authors acknowledge financial support from Brazilian agencies CAPES (Project 018/05) and CNPq (Project 134576/2007–1).

references
References top

Arslan, H., Flörke, U. & Külcü, N. (2003). Transition Met. Chem. 28, 816–819.

Coppens, P., Leiserowitz, L. & Rabinovich, D. (1965). Acta Cryst. 18, 1035–1038.

Farrugia, L. J. (1997). J. Appl. Cryst. 30, 565.

Farrugia, L. J. (1999). J. Appl. Cryst. 32, 837–838.

Hernández, W., Spodine, E., Muñoz, J. C., Beyer, L., Schröder, U., Ferreira, J. & Pavani, M. (2003). Bioinorg. Chem. Appl. 1, 271–284.

Jia, D.-X., Zhu, A.-M., Deng, J. & Zhang, Y. (2007). Z. Anorg. Allg. Chem. 633, 2059–2063.

Nonius (1998). COLLECT. Nonius BV, Delft, The Netherlands.

Otwinowski, Z. & Minor, W. (1997). Methods in Enzymology, Vol. 276, Macromolecular Crystallography, Part A, edited by C. W. Carter Jr & R. M. Sweet, pp. 307–326. New York: Academic Press.

Pérez, H., Mascarenhas, Y., Plutín, A. M., de Souza Corrêa, R. & Duque, J. (2008). Acta Cryst. E64, m503.

Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122.