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hy2119 scheme

Acta Cryst. (2008). E64, m503    [ doi:10.1107/S160053680800531X ]

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

H. Pérez, Y. Mascarenhas, A. M. Plutín, R. de Souza Corrêa and J. Duque

Abstract top

In the title compound, [Co(C20H15N2OS)3], the CoIII atom is coordinated by the S and O atoms of three N-benzoyl-N',N'-diphenylthiourea ligands in a slightly distorted octahedral geometry. The O and S atoms are in cis positions, while the positions between the O and S atoms are trans.

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). 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 and related structures, see: Arslan et al. (2003); Jia et al. (2007). For ligand synthesis, see: Hernández et al. (2003).

Experimental top

N-benzoyl-N',N'-diphenylthiourea ligand was synthesized according to a procedure described by Hernández et al. (2003), by converting benzoyl chloride into benzoyl isothiocyanate and then condensing with an appropriate amine. To an ethanol solution (30 ml) containing the ligand (0.66 g, 2 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 (Enraf–Nonius, 2000); cell refinement: DENZO (Otwinowski & Minor, 1997); data reduction: DENZO (Otwinowski & Minor, 1997); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 for Windows (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 compound.
Tris(N-benzoyl-N',N'-diphenylthioureato-κ2O,S)cobalt(III) top
Crystal data top
[Co(C20H15N2OS)3]Z = 2
Mr = 1053.13F000 = 1092
Triclinic, P1Dx = 1.316 Mg m−3
Hall symbol: -P 1Mo Kα radiation
λ = 0.71073 Å
a = 10.460 (1) ÅCell parameters from 288 reflections
b = 13.591 (5) Åθ = 2.9–26.4º
c = 20.515 (5) ŵ = 0.49 mm−1
α = 93.371 (2)ºT = 150 (2) K
β = 97.652 (5)ºBlock, green
γ = 112.212 (5)º0.22 × 0.12 × 0.03 mm
V = 2657.2 (12) Å3
Data collection top
Nonius KappaCCD
diffractometer		7633 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tubeRint = 0.057
Monochromator: graphiteθmax = 25º
φ and ω scansθmin = 3.0º
Absorption correction: Gaussian
(Coppens et al., 1965)		h = −12→12
Tmin = 0.862, Tmax = 0.971k = −16→16
16799 measured reflectionsl = −24→24
9325 independent reflections
Refinement top
Refinement on F2H-atom parameters constrained
Least-squares matrix: full  w = 1/[σ2(Fo2) + (0.0786P)2 + 0.1153P]
where P = (Fo2 + 2Fc2)/3
R[F2 > 2σ(F2)] = 0.057(Δ/σ)max < 0.001
wR(F2) = 0.162Δρmax = 0.34 e Å−3
S = 1.13Δρmin = −0.6 e Å−3
9325 reflectionsExtinction correction: none
654 parameters
Crystal data top
[Co(C20H15N2OS)3]γ = 112.212 (5)º
Mr = 1053.13V = 2657.2 (12) Å3
Triclinic, P1Z = 2
a = 10.460 (1) ÅMo Kα
b = 13.591 (5) ŵ = 0.49 mm−1
c = 20.515 (5) ÅT = 150 (2) K
α = 93.371 (2)º0.22 × 0.12 × 0.03 mm
β = 97.652 (5)º
Data collection top
Nonius KappaCCD
diffractometer		9325 independent reflections
Absorption correction: Gaussian
(Coppens et al., 1965)		7633 reflections with I > 2σ(I)
Tmin = 0.862, Tmax = 0.971Rint = 0.057
16799 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.057654 parameters
wR(F2) = 0.162H-atom parameters constrained
S = 1.13Δρmax = 0.34 e Å−3
9325 reflectionsΔρmin = −0.6 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
C10.6058 (3)0.4720 (2)0.18641 (13)0.0483 (6)
C20.3964 (3)0.4260 (2)0.10944 (13)0.0469 (6)
C30.7327 (3)0.4463 (2)0.19797 (13)0.0522 (7)
C40.8459 (3)0.5073 (3)0.24551 (16)0.0691 (9)
H40.84220.56380.2720.083*
C50.9652 (4)0.4848 (4)0.2541 (2)0.0955 (14)
H51.04170.52650.28610.115*
C60.9707 (5)0.4024 (5)0.2161 (2)0.1075 (16)
H61.05110.38780.22210.129*
C70.8597 (5)0.3404 (4)0.1690 (2)0.1022 (15)
H70.86460.28380.14320.123*
C80.7403 (4)0.3618 (3)0.15960 (18)0.0731 (9)
H80.66460.31940.12750.088*
C90.3767 (3)0.2802 (3)0.02958 (14)0.0563 (7)
C100.3225 (5)0.1780 (3)0.0435 (2)0.0945 (13)
H100.25160.15680.06890.113*
C110.3739 (7)0.1046 (4)0.0193 (3)0.134 (2)
H110.33650.03390.02820.161*
C120.4794 (7)0.1369 (5)−0.0175 (3)0.1169 (17)
H120.51390.0881−0.03340.14*
C130.5332 (5)0.2388 (4)−0.0307 (2)0.0900 (12)
H130.60560.2606−0.05530.108*
C140.4812 (3)0.3111 (3)−0.00779 (16)0.0678 (8)
H140.51730.3812−0.01780.081*
C150.1953 (3)0.3554 (2)0.01770 (14)0.0535 (7)
C160.1959 (4)0.3985 (3)−0.04118 (17)0.0737 (9)
H160.27960.4305−0.05690.088*
C170.0722 (4)0.3942 (4)−0.07690 (19)0.0913 (12)
H170.07350.4242−0.11650.11*
C18−0.0503 (4)0.3472 (4)−0.0554 (2)0.0982 (14)
H18−0.13330.3441−0.08010.118*
C19−0.0511 (4)0.3043 (5)0.0032 (2)0.1144 (18)
H19−0.13530.2720.01860.137*
C200.0719 (4)0.3084 (4)0.03974 (18)0.0858 (12)
H200.07030.2790.07960.103*
C210.6062 (3)0.8182 (2)0.19445 (14)0.0567 (7)
C220.4123 (3)0.8152 (2)0.24214 (14)0.0553 (7)
C230.7319 (3)0.8900 (3)0.16920 (16)0.0664 (8)
C240.8101 (4)0.8470 (3)0.13729 (18)0.0740 (9)
H240.78360.77310.13190.089*
C250.9257 (4)0.9102 (4)0.1135 (2)0.1016 (13)
H250.97540.87970.09080.122*
C260.9668 (6)1.0168 (5)0.1230 (4)0.153 (2)
H261.04691.06040.10790.184*
C270.8913 (6)1.0628 (4)0.1553 (4)0.159 (3)
H270.92021.13680.16160.19*
C280.7733 (5)0.9983 (3)0.1780 (3)0.1106 (14)
H280.72171.02870.19940.133*
C290.4254 (4)0.9955 (3)0.27415 (18)0.0668 (9)
C300.4007 (5)1.0494 (3)0.2228 (2)0.1031 (14)
H300.34141.0120.18380.124*
C310.4642 (6)1.1594 (4)0.2294 (3)0.1232 (18)
H310.44841.1960.19430.148*
C320.5481 (6)1.2144 (4)0.2854 (3)0.1056 (15)
H320.58741.28880.28960.127*
C330.5761 (5)1.1622 (3)0.3359 (2)0.0985 (13)
H330.63721.20060.37420.118*
C340.5135 (4)1.0506 (3)0.3307 (2)0.0827 (10)
H340.5321.01440.36550.099*
C350.2295 (4)0.8392 (2)0.29742 (17)0.0644 (8)
C360.2357 (4)0.8093 (3)0.36055 (18)0.0777 (10)
H360.320.81310.38420.093*
C370.1148 (5)0.7735 (3)0.3880 (2)0.0885 (12)
H370.11810.7520.43020.106*
C38−0.0086 (5)0.7691 (3)0.3545 (3)0.0952 (13)
H38−0.08870.74610.37390.114*
C39−0.0140 (5)0.7985 (4)0.2924 (3)0.1089 (15)
H39−0.09850.7950.26910.131*
C400.1056 (4)0.8338 (3)0.2636 (2)0.0895 (12)
H400.10110.85370.2210.107*
C410.5351 (3)0.6913 (2)0.36616 (13)0.0522 (7)
C420.3583 (3)0.5191 (2)0.35847 (13)0.0518 (7)
C430.6139 (3)0.7917 (2)0.41223 (14)0.0572 (7)
C440.7273 (4)0.8716 (3)0.39512 (18)0.0734 (9)
H440.75390.86340.35430.088*
C450.8020 (5)0.9639 (3)0.4379 (2)0.1027 (15)
H450.8791.01740.42620.123*
C460.7623 (6)0.9761 (4)0.4975 (2)0.1163 (17)
H460.81381.03750.52690.14*
C470.6478 (6)0.8992 (4)0.5144 (2)0.1141 (17)
H470.61910.90980.55430.137*
C480.5748 (4)0.8064 (3)0.47290 (17)0.0822 (11)
H480.49870.7530.48540.099*
C490.2637 (3)0.4864 (2)0.46147 (15)0.0583 (7)
C500.1969 (4)0.5550 (3)0.46646 (17)0.0748 (9)
H500.16620.58010.42880.09*
C510.1750 (4)0.5869 (3)0.52809 (19)0.0847 (11)
H510.12930.63330.53180.102*
C520.2211 (4)0.5497 (3)0.58357 (19)0.0822 (11)
H520.20620.57080.62490.099*
C530.2890 (4)0.4818 (3)0.57807 (18)0.0847 (11)
H530.32090.45730.61580.102*
C540.3106 (4)0.4492 (3)0.51650 (17)0.0751 (9)
H540.35630.40280.51270.09*
C550.2017 (4)0.3380 (3)0.37298 (16)0.0625 (8)
C560.0584 (4)0.2992 (3)0.3611 (2)0.0851 (11)
H560.01210.34410.36890.102*
C57−0.0175 (5)0.1915 (4)0.3370 (3)0.1113 (16)
H57−0.11480.16460.32820.134*
C580.0513 (7)0.1254 (4)0.3263 (3)0.1168 (17)
H580.00040.05360.31050.14*
C590.1918 (6)0.1639 (4)0.3386 (3)0.1068 (15)
H590.23780.11870.33110.128*
C600.2684 (4)0.2704 (3)0.3622 (2)0.0830 (11)
H600.36570.29640.37080.1*
N10.5092 (2)0.4108 (2)0.13594 (11)0.0542 (6)
N20.3234 (2)0.3561 (2)0.05438 (11)0.0532 (6)
N30.5350 (3)0.8671 (2)0.22344 (13)0.0613 (6)
N40.3564 (3)0.8799 (2)0.26916 (13)0.0634 (7)
N50.4330 (3)0.61702 (19)0.38961 (11)0.0557 (6)
N60.2803 (3)0.4495 (2)0.39679 (12)0.0597 (6)
O10.6057 (2)0.54725 (16)0.22486 (10)0.0576 (5)
O20.5835 (2)0.72042 (17)0.18653 (10)0.0611 (5)
O30.5765 (2)0.68743 (16)0.31129 (9)0.0561 (5)
S10.33442 (8)0.52013 (7)0.13271 (4)0.0583 (2)
S20.31150 (8)0.68008 (6)0.23515 (4)0.0580 (2)
S30.34463 (8)0.46920 (6)0.27777 (4)0.0569 (2)
Co10.46544 (4)0.60548 (3)0.228631 (17)0.05040 (14)
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
C10.0521 (15)0.0543 (16)0.0415 (14)0.0212 (13)0.0147 (12)0.0109 (12)
C20.0520 (15)0.0505 (15)0.0406 (14)0.0206 (12)0.0138 (12)0.0066 (11)
C30.0510 (15)0.0656 (18)0.0443 (15)0.0248 (14)0.0137 (12)0.0123 (13)
C40.0580 (18)0.095 (3)0.0499 (17)0.0253 (17)0.0081 (14)0.0105 (16)
C50.055 (2)0.162 (4)0.068 (2)0.041 (2)0.0051 (17)0.021 (3)
C60.082 (3)0.190 (5)0.086 (3)0.088 (3)0.021 (2)0.023 (3)
C70.096 (3)0.153 (4)0.094 (3)0.089 (3)0.018 (3)0.008 (3)
C80.069 (2)0.089 (3)0.071 (2)0.0436 (19)0.0102 (17)0.0014 (18)
C90.0630 (17)0.0615 (18)0.0483 (16)0.0301 (15)0.0080 (13)−0.0010 (13)
C100.122 (3)0.076 (3)0.107 (3)0.053 (2)0.046 (3)0.026 (2)
C110.185 (6)0.085 (3)0.172 (6)0.084 (4)0.059 (5)0.036 (3)
C120.165 (5)0.130 (4)0.109 (4)0.112 (4)0.037 (4)0.008 (3)
C130.099 (3)0.129 (4)0.068 (2)0.074 (3)0.015 (2)−0.001 (2)
C140.070 (2)0.084 (2)0.0570 (18)0.0390 (18)0.0137 (15)−0.0014 (16)
C150.0559 (16)0.0611 (18)0.0451 (15)0.0265 (14)0.0050 (12)0.0002 (13)
C160.071 (2)0.093 (3)0.0577 (19)0.0288 (19)0.0153 (16)0.0235 (18)
C170.088 (3)0.127 (4)0.066 (2)0.048 (3)0.007 (2)0.038 (2)
C180.074 (2)0.158 (4)0.074 (3)0.059 (3)0.004 (2)0.028 (3)
C190.061 (2)0.193 (5)0.090 (3)0.044 (3)0.018 (2)0.050 (3)
C200.067 (2)0.133 (4)0.061 (2)0.037 (2)0.0155 (17)0.036 (2)
C210.0709 (19)0.0569 (18)0.0443 (15)0.0253 (15)0.0160 (14)0.0032 (13)
C220.0697 (18)0.0557 (17)0.0484 (16)0.0313 (15)0.0164 (14)0.0054 (13)
C230.073 (2)0.063 (2)0.0609 (19)0.0215 (16)0.0237 (16)0.0033 (15)
C240.071 (2)0.078 (2)0.072 (2)0.0268 (18)0.0225 (18)0.0010 (18)
C250.0880.097 (3)0.125 (4)0.031 (2)0.053 (2)0.011 (3)
C260.1330.103 (4)0.232 (7)0.025 (3)0.120 (4)0.034 (4)
C270.1370.071 (3)0.278 (9)0.022 (3)0.121 (4)0.029 (4)
C280.120.065 (2)0.153 (4)0.026 (2)0.073 (3)0.013 (3)
C290.081 (2)0.0542 (18)0.077 (2)0.0317 (17)0.0355 (18)0.0091 (16)
C300.143 (4)0.074 (3)0.085 (3)0.034 (3)0.016 (3)0.022 (2)
C310.173 (5)0.069 (3)0.122 (4)0.036 (3)0.026 (4)0.042 (3)
C320.135 (4)0.059 (2)0.117 (4)0.022 (3)0.047 (3)0.017 (3)
C330.102 (3)0.075 (3)0.097 (3)0.013 (2)0.019 (2)−0.005 (2)
C340.096 (3)0.064 (2)0.084 (3)0.026 (2)0.019 (2)0.0080 (19)
C350.081 (2)0.0531 (18)0.071 (2)0.0345 (16)0.0291 (17)0.0042 (15)
C360.093 (3)0.080 (2)0.069 (2)0.038 (2)0.0292 (19)0.0081 (18)
C370.126 (3)0.078 (3)0.077 (2)0.045 (2)0.051 (3)0.0134 (19)
C380.105 (3)0.080 (3)0.126 (4)0.048 (2)0.064 (3)0.019 (2)
C390.086 (3)0.133 (4)0.133 (4)0.062 (3)0.037 (3)0.031 (3)
C400.097 (3)0.105 (3)0.096 (3)0.062 (2)0.037 (2)0.037 (2)
C410.0597 (16)0.0582 (17)0.0428 (15)0.0271 (14)0.0105 (13)0.0049 (12)
C420.0602 (16)0.0558 (17)0.0435 (15)0.0262 (14)0.0107 (13)0.0091 (12)
C430.0668 (18)0.0590 (18)0.0464 (16)0.0270 (15)0.0068 (13)−0.0002 (13)
C440.078 (2)0.070 (2)0.064 (2)0.0184 (18)0.0174 (17)−0.0032 (17)
C450.111 (3)0.069 (2)0.095 (3)0.000 (2)0.023 (3)−0.016 (2)
C460.141 (4)0.085 (3)0.088 (3)0.014 (3)0.017 (3)−0.037 (3)
C470.149 (4)0.098 (3)0.075 (3)0.026 (3)0.033 (3)−0.027 (2)
C480.106 (3)0.079 (2)0.055 (2)0.028 (2)0.0250 (19)−0.0085 (17)
C490.0646 (18)0.0595 (18)0.0517 (17)0.0221 (15)0.0173 (14)0.0106 (14)
C500.097 (2)0.083 (2)0.059 (2)0.047 (2)0.0255 (18)0.0180 (17)
C510.105 (3)0.095 (3)0.074 (2)0.054 (2)0.035 (2)0.012 (2)
C520.095 (3)0.095 (3)0.060 (2)0.034 (2)0.0327 (19)0.0102 (19)
C530.101 (3)0.104 (3)0.053 (2)0.040 (2)0.0191 (19)0.0177 (19)
C540.092 (2)0.085 (2)0.060 (2)0.045 (2)0.0193 (18)0.0199 (18)
C550.076 (2)0.0565 (18)0.0569 (18)0.0241 (16)0.0196 (15)0.0118 (14)
C560.080 (3)0.075 (2)0.098 (3)0.025 (2)0.023 (2)0.008 (2)
C570.084 (3)0.085 (3)0.137 (4)0.006 (2)0.018 (3)−0.003 (3)
C580.137 (4)0.062 (3)0.133 (4)0.016 (3)0.038 (4)−0.001 (3)
C590.134 (4)0.066 (3)0.130 (4)0.045 (3)0.041 (3)0.010 (2)
C600.094 (3)0.063 (2)0.102 (3)0.037 (2)0.027 (2)0.016 (2)
N10.0537 (13)0.0633 (15)0.0472 (13)0.0275 (12)0.0045 (11)−0.0044 (11)
N20.0539 (13)0.0634 (15)0.0448 (13)0.0280 (12)0.0050 (10)−0.0022 (11)
N30.0752 (16)0.0557 (15)0.0592 (15)0.0277 (13)0.0261 (13)0.0055 (12)
N40.0788 (17)0.0516 (14)0.0708 (17)0.0309 (13)0.0330 (14)0.0078 (12)
N50.0651 (15)0.0552 (14)0.0459 (13)0.0215 (12)0.0137 (11)0.0044 (11)
N60.0744 (16)0.0534 (14)0.0524 (14)0.0233 (13)0.0181 (12)0.0092 (11)
O10.0645 (12)0.0599 (12)0.0493 (11)0.0280 (10)0.0051 (9)−0.0025 (9)
O20.0790 (14)0.0606 (13)0.0504 (11)0.0301 (11)0.0250 (10)0.0049 (9)
O30.0648 (12)0.0574 (12)0.0442 (11)0.0202 (10)0.0165 (9)0.0007 (9)
S10.0745 (5)0.0677 (5)0.0434 (4)0.0429 (4)0.0027 (3)−0.0004 (3)
S20.0676 (5)0.0544 (4)0.0583 (4)0.0291 (4)0.0179 (4)0.0036 (3)
S30.0691 (5)0.0532 (4)0.0457 (4)0.0218 (4)0.0080 (3)0.0026 (3)
Co10.0635 (3)0.0525 (3)0.0396 (2)0.02712 (19)0.01122 (17)0.00224 (16)
Geometric parameters (Å, °) top
C1—O11.254 (3)C32—C331.351 (7)
C1—N11.331 (4)C32—H320.93
C1—C31.489 (4)C33—C341.397 (5)
C2—N11.325 (4)C33—H330.93
C2—N21.362 (3)C34—H340.93
C2—S11.710 (3)C35—C401.360 (5)
C3—C41.377 (4)C35—C361.381 (5)
C3—C81.388 (4)C35—N41.447 (4)
C4—C51.385 (5)C36—C371.382 (5)
C4—H40.93C36—H360.93
C5—C61.351 (7)C37—C381.358 (6)
C5—H50.93C37—H370.93
C6—C71.363 (6)C38—C391.357 (7)
C6—H60.93C38—H380.93
C7—C81.378 (5)C39—C401.387 (6)
C7—H70.93C39—H390.93
C8—H80.93C40—H400.93
C9—C101.351 (5)C41—O31.264 (3)
C9—C141.368 (4)C41—N51.330 (4)
C9—N21.444 (4)C41—C431.491 (4)
C10—C111.395 (6)C42—N51.331 (4)
C10—H100.93C42—N61.362 (4)
C11—C121.370 (7)C42—S31.718 (3)
C11—H110.93C43—C441.376 (5)
C12—C131.343 (7)C43—C481.387 (4)
C12—H120.93C44—C451.379 (5)
C13—C141.378 (5)C44—H440.93
C13—H130.93C45—C461.363 (6)
C14—H140.93C45—H450.93
C15—C201.359 (4)C46—C471.361 (6)
C15—C161.373 (4)C46—H460.93
C15—N21.442 (4)C47—C481.369 (5)
C16—C171.378 (5)C47—H470.93
C16—H160.93C48—H480.93
C17—C181.345 (5)C49—C501.368 (5)
C17—H170.93C49—C541.370 (5)
C18—C191.367 (6)C49—N61.446 (4)
C18—H180.93C50—C511.388 (5)
C19—C201.380 (5)C50—H500.93
C19—H190.93C51—C521.374 (6)
C20—H200.93C51—H510.93
C21—O21.256 (4)C52—C531.370 (5)
C21—N31.339 (4)C52—H520.93
C21—C231.490 (4)C53—C541.388 (5)
C22—N31.331 (4)C53—H530.93
C22—N41.357 (4)C54—H540.93
C22—S21.723 (3)C55—C561.369 (5)
C23—C281.362 (5)C55—C601.373 (5)
C23—C241.378 (4)C55—N61.439 (4)
C24—C251.364 (5)C56—C571.395 (6)
C24—H240.93C56—H560.93
C25—C261.340 (7)C57—C581.372 (7)
C25—H250.93C57—H570.93
C26—C271.384 (7)C58—C591.342 (7)
C26—H260.93C58—H580.93
C27—C281.375 (6)C59—C601.381 (6)
C27—H270.93C59—H590.93
C28—H280.93C60—H600.93
C29—C341.359 (5)O1—Co11.920 (2)
C29—C301.368 (6)O2—Co11.923 (2)
C29—N41.450 (4)O3—Co11.934 (2)
C30—C311.377 (6)S1—Co12.2153 (9)
C30—H300.93S2—Co12.2169 (11)
C31—C321.335 (7)S3—Co12.1985 (10)
C31—H310.93
O1—C1—N1129.8 (3)C37—C36—H36120.5
O1—C1—C3116.1 (2)C38—C37—C36121.2 (4)
N1—C1—C3114.0 (2)C38—C37—H37119.4
N1—C2—N2113.0 (2)C36—C37—H37119.4
N1—C2—S1129.9 (2)C39—C38—C37119.5 (4)
N2—C2—S1117.0 (2)C39—C38—H38120.3
C4—C3—C8118.7 (3)C37—C38—H38120.3
C4—C3—C1120.9 (3)C38—C39—C40120.5 (5)
C8—C3—C1120.3 (3)C38—C39—H39119.8
C3—C4—C5120.3 (4)C40—C39—H39119.8
C3—C4—H4119.9C35—C40—C39120.0 (4)
C5—C4—H4119.9C35—C40—H40120
C6—C5—C4120.1 (4)C39—C40—H40120
C6—C5—H5120O3—C41—N5129.1 (3)
C4—C5—H5120O3—C41—C43115.9 (3)
C5—C6—C7120.8 (4)N5—C41—C43115.0 (2)
C5—C6—H6119.6N5—C42—N6114.2 (2)
C7—C6—H6119.6N5—C42—S3129.7 (2)
C6—C7—C8120.0 (4)N6—C42—S3116.1 (2)
C6—C7—H7120C44—C43—C48118.8 (3)
C8—C7—H7120C44—C43—C41120.3 (3)
C7—C8—C3120.2 (4)C48—C43—C41120.9 (3)
C7—C8—H8119.9C43—C44—C45120.6 (3)
C3—C8—H8119.9C43—C44—H44119.7
C10—C9—C14120.0 (3)C45—C44—H44119.7
C10—C9—N2119.5 (3)C46—C45—C44119.6 (4)
C14—C9—N2120.5 (3)C46—C45—H45120.2
C9—C10—C11119.4 (4)C44—C45—H45120.2
C9—C10—H10120.3C47—C46—C45120.6 (4)
C11—C10—H10120.3C47—C46—H46119.7
C12—C11—C10119.9 (5)C45—C46—H46119.7
C12—C11—H11120.1C46—C47—C48120.2 (4)
C10—C11—H11120.1C46—C47—H47119.9
C13—C12—C11120.3 (4)C48—C47—H47119.9
C13—C12—H12119.9C47—C48—C43120.2 (4)
C11—C12—H12119.9C47—C48—H48119.9
C12—C13—C14120.0 (4)C43—C48—H48119.9
C12—C13—H13120C50—C49—C54121.0 (3)
C14—C13—H13120C50—C49—N6119.3 (3)
C9—C14—C13120.4 (4)C54—C49—N6119.6 (3)
C9—C14—H14119.8C49—C50—C51119.6 (3)
C13—C14—H14119.8C49—C50—H50120.2
C20—C15—C16119.2 (3)C51—C50—H50120.2
C20—C15—N2120.4 (3)C52—C51—C50119.8 (4)
C16—C15—N2120.4 (3)C52—C51—H51120.1
C15—C16—C17119.9 (3)C50—C51—H51120.1
C15—C16—H16120C53—C52—C51120.1 (3)
C17—C16—H16120C53—C52—H52120
C18—C17—C16121.1 (4)C51—C52—H52120
C18—C17—H17119.5C52—C53—C54120.3 (4)
C16—C17—H17119.5C52—C53—H53119.8
C17—C18—C19119.1 (4)C54—C53—H53119.8
C17—C18—H18120.4C49—C54—C53119.2 (4)
C19—C18—H18120.4C49—C54—H54120.4
C18—C19—C20120.5 (4)C53—C54—H54120.4
C18—C19—H19119.8C56—C55—C60119.6 (3)
C20—C19—H19119.8C56—C55—N6119.4 (3)
C15—C20—C19120.2 (3)C60—C55—N6120.9 (3)
C15—C20—H20119.9C55—C56—C57119.3 (4)
C19—C20—H20119.9C55—C56—H56120.3
O2—C21—N3129.2 (3)C57—C56—H56120.3
O2—C21—C23115.1 (3)C58—C57—C56120.1 (4)
N3—C21—C23115.7 (3)C58—C57—H57120
N3—C22—N4114.2 (3)C56—C57—H57120
N3—C22—S2130.4 (2)C59—C58—C57120.2 (4)
N4—C22—S2115.3 (2)C59—C58—H58119.9
C28—C23—C24118.7 (3)C57—C58—H58119.9
C28—C23—C21121.3 (3)C58—C59—C60120.3 (4)
C24—C23—C21120.0 (3)C58—C59—H59119.8
C25—C24—C23121.5 (4)C60—C59—H59119.8
C25—C24—H24119.2C55—C60—C59120.4 (4)
C23—C24—H24119.2C55—C60—H60119.8
C26—C25—C24119.4 (4)C59—C60—H60119.8
C26—C25—H25120.3C2—N1—C1126.2 (2)
C24—C25—H25120.3C2—N2—C15123.3 (2)
C25—C26—C27120.6 (4)C2—N2—C9119.4 (2)
C25—C26—H26119.7C15—N2—C9117.3 (2)
C27—C26—H26119.7C22—N3—C21123.7 (3)
C28—C27—C26119.6 (5)C22—N4—C35122.7 (3)
C28—C27—H27120.2C22—N4—C29121.3 (2)
C26—C27—H27120.2C35—N4—C29115.9 (2)
C23—C28—C27120.1 (4)C41—N5—C42124.2 (2)
C23—C28—H28120C42—N6—C55121.9 (2)
C27—C28—H28120C42—N6—C49121.0 (2)
C34—C29—C30119.9 (4)C55—N6—C49116.9 (2)
C34—C29—N4119.5 (3)C1—O1—Co1130.12 (18)
C30—C29—N4120.5 (4)C21—O2—Co1129.07 (18)
C29—C30—C31119.5 (5)C41—O3—Co1126.90 (19)
C29—C30—H30120.2C2—S1—Co1106.23 (10)
C31—C30—H30120.2C22—S2—Co1103.40 (11)
C32—C31—C30121.0 (5)C42—S3—Co1106.22 (10)
C32—C31—H31119.5O1—Co1—O285.41 (9)
C30—C31—H31119.5O1—Co1—O387.12 (9)
C31—C32—C33120.1 (4)O2—Co1—O385.99 (9)
C31—C32—H32119.9O1—Co1—S389.85 (7)
C33—C32—H32119.9O2—Co1—S3175.21 (7)
C32—C33—C34120.2 (4)O3—Co1—S393.07 (7)
C32—C33—H33119.9O1—Co1—S195.85 (7)
C34—C33—H33119.9O2—Co1—S192.24 (7)
C29—C34—C33119.2 (4)O3—Co1—S1176.42 (7)
C29—C34—H34120.4S3—Co1—S188.94 (4)
C33—C34—H34120.4O1—Co1—S2177.27 (7)
C40—C35—C36119.8 (3)O2—Co1—S292.85 (7)
C40—C35—N4120.8 (3)O3—Co1—S290.66 (7)
C36—C35—N4119.4 (3)S3—Co1—S291.86 (4)
C35—C36—C37119.0 (4)S1—Co1—S286.31 (4)
C35—C36—H36120.5
O1—C1—C3—C4−4.2 (4)N2—C2—N1—C1174.2 (3)
N1—C1—C3—C4175.6 (3)S1—C2—N1—C1−4.0 (4)
O1—C1—C3—C8177.5 (3)O1—C1—N1—C29.7 (5)
N1—C1—C3—C8−2.7 (4)C3—C1—N1—C2−170.1 (3)
C8—C3—C4—C50.6 (5)N1—C2—N2—C15178.7 (2)
C1—C3—C4—C5−177.7 (3)S1—C2—N2—C15−2.9 (4)
C3—C4—C5—C6−0.4 (6)N1—C2—N2—C9−3.1 (4)
C4—C5—C6—C70.0 (7)S1—C2—N2—C9175.3 (2)
C5—C6—C7—C80.2 (8)C20—C15—N2—C2−79.4 (4)
C6—C7—C8—C30.1 (7)C16—C15—N2—C2103.1 (4)
C4—C3—C8—C7−0.5 (5)C20—C15—N2—C9102.3 (4)
C1—C3—C8—C7177.8 (3)C16—C15—N2—C9−75.2 (4)
C14—C9—C10—C11−0.1 (7)C10—C9—N2—C2100.3 (4)
N2—C9—C10—C11179.8 (4)C14—C9—N2—C2−79.9 (4)
C9—C10—C11—C120.7 (9)C10—C9—N2—C15−81.4 (4)
C10—C11—C12—C13−0.3 (9)C14—C9—N2—C1598.5 (3)
C11—C12—C13—C14−0.7 (8)N4—C22—N3—C21−178.5 (3)
C10—C9—C14—C13−0.9 (5)S2—C22—N3—C21−0.8 (5)
N2—C9—C14—C13179.2 (3)O2—C21—N3—C22−9.2 (5)
C12—C13—C14—C91.3 (6)C23—C21—N3—C22172.3 (3)
C20—C15—C16—C170.3 (6)N3—C22—N4—C35−174.9 (3)
N2—C15—C16—C17177.9 (3)S2—C22—N4—C357.1 (4)
C15—C16—C17—C18−0.7 (7)N3—C22—N4—C292.1 (4)
C16—C17—C18—C190.7 (8)S2—C22—N4—C29−176.0 (3)
C17—C18—C19—C20−0.3 (9)C40—C35—N4—C22−102.6 (4)
C16—C15—C20—C190.0 (6)C36—C35—N4—C2279.8 (4)
N2—C15—C20—C19−177.5 (4)C40—C35—N4—C2980.2 (4)
C18—C19—C20—C150.0 (8)C36—C35—N4—C29−97.3 (4)
O2—C21—C23—C28−176.1 (4)C34—C29—N4—C22−93.6 (4)
N3—C21—C23—C282.6 (5)C30—C29—N4—C2287.4 (5)
O2—C21—C23—C242.7 (5)C34—C29—N4—C3583.6 (4)
N3—C21—C23—C24−178.6 (3)C30—C29—N4—C35−95.4 (4)
C28—C23—C24—C25−1.3 (6)O3—C41—N5—C423.5 (5)
C21—C23—C24—C25179.9 (4)C43—C41—N5—C42−174.3 (3)
C23—C24—C25—C262.1 (8)N6—C42—N5—C41167.0 (3)
C24—C25—C26—C27−1.6 (11)S3—C42—N5—C41−13.9 (5)
C25—C26—C27—C280.3 (12)N5—C42—N6—C55−175.0 (3)
C24—C23—C28—C27−0.1 (8)S3—C42—N6—C555.8 (4)
C21—C23—C28—C27178.7 (5)N5—C42—N6—C4910.1 (4)
C26—C27—C28—C230.6 (11)S3—C42—N6—C49−169.0 (2)
C34—C29—C30—C31−0.9 (7)C56—C55—N6—C42−110.8 (4)
N4—C29—C30—C31178.2 (4)C60—C55—N6—C4269.3 (4)
C29—C30—C31—C32−0.9 (9)C56—C55—N6—C4964.3 (4)
C30—C31—C32—C332.4 (9)C60—C55—N6—C49−115.7 (4)
C31—C32—C33—C34−2.3 (8)C50—C49—N6—C4263.7 (4)
C30—C29—C34—C331.0 (6)C54—C49—N6—C42−118.7 (4)
N4—C29—C34—C33−178.0 (3)C50—C49—N6—C55−111.4 (4)
C32—C33—C34—C290.5 (7)C54—C49—N6—C5566.2 (4)
C40—C35—C36—C370.4 (5)N1—C1—O1—Co11.0 (4)
N4—C35—C36—C37178.0 (3)C3—C1—O1—Co1−179.22 (17)
C35—C36—C37—C38−1.1 (6)N3—C21—O2—Co1−15.1 (5)
C36—C37—C38—C391.2 (7)C23—C21—O2—Co1163.5 (2)
C37—C38—C39—C40−0.6 (7)N5—C41—O3—Co129.3 (4)
C36—C35—C40—C390.1 (6)C43—C41—O3—Co1−152.9 (2)
N4—C35—C40—C39−177.4 (4)N1—C2—S1—Co1−7.9 (3)
C38—C39—C40—C35−0.1 (7)N2—C2—S1—Co1174.04 (18)
O3—C41—C43—C44−2.2 (4)N3—C22—S2—Co124.0 (3)
N5—C41—C43—C44175.9 (3)N4—C22—S2—Co1−158.4 (2)
O3—C41—C43—C48177.8 (3)N5—C42—S3—Co1−4.7 (3)
N5—C41—C43—C48−4.1 (5)N6—C42—S3—Co1174.3 (2)
C48—C43—C44—C451.0 (6)C1—O1—Co1—O2−102.9 (2)
C41—C43—C44—C45−179.0 (4)C1—O1—Co1—O3170.9 (2)
C43—C44—C45—C46−0.5 (7)C1—O1—Co1—S377.8 (2)
C44—C45—C46—C47−1.5 (9)C1—O1—Co1—S1−11.1 (2)
C45—C46—C47—C482.9 (9)C21—O2—Co1—O1−144.6 (3)
C46—C47—C48—C43−2.4 (8)C21—O2—Co1—O3−57.2 (3)
C44—C43—C48—C470.4 (6)C21—O2—Co1—S1119.7 (3)
C41—C43—C48—C47−179.6 (4)C21—O2—Co1—S233.3 (3)
C54—C49—C50—C51−0.6 (6)C41—O3—Co1—O1−127.1 (2)
N6—C49—C50—C51177.1 (3)C41—O3—Co1—O2147.3 (2)
C49—C50—C51—C520.3 (6)C41—O3—Co1—S3−37.4 (2)
C50—C51—C52—C530.3 (6)C41—O3—Co1—S254.5 (2)
C51—C52—C53—C54−0.6 (6)C42—S3—Co1—O1109.02 (12)
C50—C49—C54—C530.3 (6)C42—S3—Co1—O321.91 (12)
N6—C49—C54—C53−177.4 (3)C42—S3—Co1—S1−155.12 (11)
C52—C53—C54—C490.3 (6)C42—S3—Co1—S2−68.85 (11)
C60—C55—C56—C57−1.1 (6)C2—S1—Co1—O111.72 (12)
N6—C55—C56—C57179.0 (4)C2—S1—Co1—O297.33 (12)
C55—C56—C57—C580.9 (7)C2—S1—Co1—S3−78.02 (10)
C56—C57—C58—C59−0.4 (9)C2—S1—Co1—S2−169.95 (10)
C57—C58—C59—C600.2 (9)C22—S2—Co1—O2−30.16 (12)
C56—C55—C60—C590.9 (6)C22—S2—Co1—O355.86 (12)
N6—C55—C60—C59−179.2 (4)C22—S2—Co1—S3148.96 (11)
C58—C59—C60—C55−0.4 (7)C22—S2—Co1—S1−122.23 (11)
Table 1
Selected geometric parameters (Å, °) top
O1—Co11.920 (2)S1—Co12.2153 (9)
O2—Co11.923 (2)S2—Co12.2169 (11)
O3—Co11.934 (2)S3—Co12.1985 (10)
O1—Co1—O285.41 (9)O3—Co1—S1176.42 (7)
O1—Co1—O387.12 (9)S3—Co1—S188.94 (4)
O2—Co1—O385.99 (9)O1—Co1—S2177.27 (7)
O1—Co1—S389.85 (7)O2—Co1—S292.85 (7)
O2—Co1—S3175.21 (7)O3—Co1—S290.66 (7)
O3—Co1—S393.07 (7)S3—Co1—S291.86 (4)
O1—Co1—S195.85 (7)S1—Co1—S286.31 (4)
O2—Co1—S192.24 (7)
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 (Proyect 134576/2007–1).

references
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