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Acta Crystallogr Sect E Struct Rep Online. 2008 March 1; 64(Pt 3): m503.
Published online 2008 February 29. doi:  10.1107/S160053680800531X
PMCID: PMC2960879

Tris(N-benzoyl-N′,N′-diphenyl­thio­ureato-κ2 O,S)cobalt(III)

Abstract

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.

Related literature

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

An external file that holds a picture, illustration, etc.
Object name is e-64-0m503-scheme1.jpg

Experimental

Crystal data

  • [Co(C20H15N2OS)3]
  • M r = 1053.13
  • Triclinic, An external file that holds a picture, illustration, etc.
Object name is e-64-0m503-efi1.jpg
  • a = 10.460 (1) Å
  • b = 13.591 (5) Å
  • c = 20.515 (5) Å
  • α = 93.371 (2)°
  • β = 97.652 (5)°
  • γ = 112.212 (5)°
  • V = 2657.2 (12) Å3
  • Z = 2
  • Mo Kα radiation
  • μ = 0.49 mm−1
  • T = 150 (2) K
  • 0.22 × 0.12 × 0.03 mm

Data collection

  • Nonius KappaCCD diffractometer
  • Absorption correction: Gaussian (Coppens et al., 1965 [triangle]) T min = 0.862, T max = 0.971
  • 16799 measured reflections
  • 9325 independent reflections
  • 7633 reflections with I > 2σ(I)
  • R int = 0.057

Refinement

  • R[F 2 > 2σ(F 2)] = 0.057
  • wR(F 2) = 0.162
  • S = 1.13
  • 9325 reflections
  • 654 parameters
  • H-atom parameters constrained
  • Δρmax = 0.34 e Å−3
  • Δρmin = −0.6 e Å−3

Data collection: COLLECT (Enraf–Nonius, 2000); cell refinement: DENZO (Otwinowski & Minor, 1997 [triangle]); data reduction: DENZO; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 [triangle]); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 [triangle]); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997 [triangle]); software used to prepare material for publication: WinGX (Farrugia, 1999 [triangle]).

Table 1
Selected geometric parameters (Å, °)

Supplementary Material

Crystal structure: contains datablocks global, I. DOI: 10.1107/S160053680800531X/hy2119sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S160053680800531X/hy2119Isup2.hkl

Additional supplementary materials: crystallographic information; 3D view; checkCIF report

Acknowledgments

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).

supplementary crystallographic information

Comment

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.

Experimental

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

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

Figures

Fig. 1.
The molecular structure of the title compound. Displacement ellipsoids are drawn at the 50% probability level.
Fig. 2.
View of the unit cell of the title compound.

Crystal data

[Co(C20H15N2OS)3]Z = 2
Mr = 1053.13F000 = 1092
Triclinic, P1Dx = 1.316 Mg m3
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 mm1
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

Nonius KappaCCD diffractometer7633 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tubeRint = 0.057
Monochromator: graphiteθmax = 25º
[var phi] 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

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 Å3
S = 1.13Δρmin = −0.6 e Å3
9325 reflectionsExtinction correction: none
654 parameters

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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2)

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)

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, °)

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)

Footnotes

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: HY2119).

References

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  • Hernández, W., Spodine, E., Muñoz, J. C., Beyer, L., Schröder, U., Ferreira, J. & Pavani, M. (2003). Bioinorg. Chem. Appl.1, 271–284. [PMC free article] [PubMed]
  • Jia, D.-X., Zhu, A.-M., Deng, J. & Zhang, Y. (2007). Z. Anorg. Allg. Chem.633, 2059–2063.
  • Otwinowski, Z. & Minor, W. (1997). Methods in Enzymology, Vol. 276, Macromolecular Crystallography, Part A, edited by C. W. Carter Jr and R. M. Sweet, pp. 307–326. New York: Academic Press.
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