PMCCPMCCPMCC

Search tips
Search criteria 

Advanced

 
Logo of actaeInternational Union of Crystallographysearchopen accessarticle submissionjournal home pagethis article
 
Acta Crystallogr Sect E Struct Rep Online. 2008 May 1; 64(Pt 5): m635–m636.
Published online 2008 April 10. doi:  10.1107/S1600536808008970
PMCID: PMC2961332

(Carbonyl-1κC)bis­[2,3(η5)-cyclo­penta­dien­yl][μ3-(S-methyl trithio­carbonato)methylidyne-1:2:3κ4 C,S′′:C:C](triphenyl­phosphine-1κP)(μ3-sulfido-1:2:3κ3 S)dicobalt(II)iron(II) trifluoro­methane­sulfonate

Abstract

The asymmetric unit of the title compound, [FeCo2(C5H5)2(C3H3S3)S(C18H15P)(CO)]CF3SO3, consists of a triangular irondicobalt cluster cation and a trifluoro­methane­sulfonate anion. In the cation, the FeCo2 triangle is symmetrically capped on one face by an S atom and on the other by a C atom linked to a methyl trithio­carbonate residue that bridges the Fe—C bond. Each Co atom carries a cyclo­penta­dienyl ligand while the Fe atom coordinates to one carbonyl and one triphenyl­phosphine ligand. In the crystal structure, the cation is linked to the anion by a number of weak non-classical C—H(...)O and C—H(...)F hydrogen bonds and weak S(...)O (3.317 Å) and S(...)F (3.198 Å) inter­actions. The structure is further stabilized by additional inter­molecular C—H(...)O, C—H(...)F and O(...)O (2.942 Å) contacts, together with an unusual S(...)π(Cp) inter­action (S(...)centroid distance = 3.385 Å), generating an extended network.

Related literature

For the preparation of the title compound, see: Manning et al. (2003 [triangle]). For reference structural data, see: Allen et al. (1987 [triangle], 2002 [triangle]). For related sulfur- and carbon-capped triangular FeCo2 structures, see: Manning, O’Dwyer et al, (1995 [triangle], 1998 [triangle], 1999 [triangle]); Manning, Palmer et al. (1998 [triangle]). For related literature, see: Ringer et al. (2007 [triangle]).

An external file that holds a picture, illustration, etc.
Object name is e-64-0m635-scheme1.jpg

Experimental

Crystal data

  • [FeCo2(C5H5)2(C3H3S3)S(C18H15P)(CO)]CF3SO3
  • M r = 910.53
  • Monoclinic, An external file that holds a picture, illustration, etc.
Object name is e-64-0m635-efi1.jpg
  • a = 11.0403 (6) Å
  • b = 29.2183 (14) Å
  • c = 10.9040 (5) Å
  • β = 100.664 (3)°
  • V = 3456.7 (3) Å3
  • Z = 4
  • Mo Kα radiation
  • μ = 1.77 mm−1
  • T = 91 (2) K
  • 0.18 × 0.06 × 0.06 mm

Data collection

  • Bruker APEXII CCD area-detector diffractometer
  • Absorption correction: multi-scan (SADABS; Bruker, 2006 [triangle]) T min = 0.717, T max = 0.899
  • 36119 measured reflections
  • 5502 independent reflections
  • 4297 reflections with I > 2σ(I)
  • R int = 0.081

Refinement

  • R[F 2 > 2σ(F 2)] = 0.031
  • wR(F 2) = 0.067
  • S = 1.03
  • 5502 reflections
  • 443 parameters
  • H-atom parameters constrained
  • Δρmax = 0.38 e Å−3
  • Δρmin = −0.35 e Å−3

Data collection: APEX2 (Bruker 2006 [triangle]); cell refinement: APEX2 and SAINT (Bruker 2006 [triangle]); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 [triangle]) and TITAN2000 (Hunter & Simpson, 1999 [triangle]); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 [triangle]) and TITAN2000; molecular graphics: ORTEP-3 (Farrugia, 1997 [triangle]) and Mercury (Macrae et al., 2006 [triangle]); software used to prepare material for publication: SHELXL97, enCIFer (Allen et al., 2004 [triangle]) and PLATON (Spek, 2003 [triangle]).

Table 1
Selected geometric parameters (Å, °)
Table 2
Hydrogen-bond geometry (Å, °)

Supplementary Material

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536808008970/hb2713sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536808008970/hb2713Isup2.hkl

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

Acknowledgments

We thank the New Zealand Foundation for Research Science and Technology for a Postdoctoral Fellowship to CJM, and the University of Otago for the purchase of the diffractometer.

supplementary crystallographic information

Comment

The title compound (I) was first reported and characterized by us (Manning et al., 2003), as part of a study into the reaction of carbon disulfide with the µ3-CS cluster [{Co(η5-C5H5)}2{Fe(CO)(PPh3)}(µ3-S)(µ3-CS)]. The product from this reaction, [{Co(η5-C5H5)}2{Fe(CO)(PPh3)}(µ3-S)(µ3-C2S3)], reacted with alkylating agents MeX to give [{Co(η5-C5H5)}2{Fe(CO)(PPh3)}(µ3-S)(µ3-C2S3Me)]\ +[X]- salts. The compound with [X]- = I- was characterized crystallographically in the initial report. Since then crystals of the compound (I) where [X]- is trifluoromethanesulfonate have come to hand allowing us to determine the effect of the counter-anion on the unusual structure of the cation.

The asymmetric unit of (I), C32H28OPS4FeCo2+, CO3F3S-, consists of a bicapped iron-dicobalt cluster cation and a trifluoromethanesulfonate anion (Fig. 1). The structure of the cation in (I) is very similar to that of the cation in the previously reported iodide salt [{Co(η5-C5H5)}2{Fe(CO)(PPh3)}(µ3-S)(µ3-C2S3Me)][I], Manning et al. (2003). The bond lengths and angles in the cations, (Table 1) are comparable in both structures. They also confirm our suggestion that the bonding within the Fe—S—C(SMe)-S—C metallocycle is delocalized. Bond distances and angles in the anion are also normal (Allen et al., 1987).

In the crystal structure the cation is linked to the anion in the asymmetric unit by a number of weak non-classical C—H···O and C—H···F hydrogen bonds and weak S···O and F···O interactions. A feature of the packing is an intermolecular S···π(Cp) interaction involving the capping S1 atom and the C21···C25 cyclopentadiene ring of an adjacent molecule (Fig. 2), with an S···Cgi distance of 3.385Å and a mean S1···Cg···Cn angle of 89.9° (Cg is the centroid of the C21···C25 cyclopentadiene ring and n = 21···25; symmetry code i = x, 3/2 - y, 1/2 + z). Such interactions between S atoms and benzene rings are common, 1781 examples with S···Cg distances in the range 3.0 ··· 3.7 Å (mean 3.54 Å) and S1···Cg···Cn angles in the range 60···120° (mean 90.0°) in the Cambridge database Ver 5.29 to January 2008 (Allen et al., 2004). They are also important in determining protein folding interactions in biochemistry (Ringer et al., 2007). In contrast however, the database reveals only 194 similar interactions involving five-membered aromatic rings with the same distance and angle limitations (mean S···Cg distance 3.62 Å, S1···Cg···Cn angle 89.9), many of which involve cyclopentadiene rings in transition metal organometallic complexes.

The structure is further stabilized by additional intermolecular C—H···O, C—H···F and O···O contacts which generate an extended network (Table 2). Pairs of cluster cations, interleave with trifluoromethylsulphonate cations to form interlinked columns down the c axis (Fig. 3).

For related sulfur and carbon capped triangular FeCo2 structures see Manning, O'Dwyer et al., (1995, 1998, 1999); Manning, Palmer et al., (1998).

Experimental

The title compound was prepared from the room temperature reaction of methyl trifluoromethanesulfonate with [{Co(η5-C5H5)}2{Fe(CO)(PPh3)}(µ3-S)(µ3-C2S3)], Manning et al. (2003), with X-ray quality crystals grown from dichloromethane layered with methanol.

Refinement

The crystals were small and weakly diffracting and little useable data were obtained beyond θ = 24°. All H-atoms bound to carbon were refined using a riding model with d(C—H) = 0.95 Å, Uiso=1.2Ueq (C) for aromatic and 0.98 Å, Uiso = 1.5Ueq (C) for CH3 H atoms.

Figures

Fig. 1.
The asymmetric unit of (I), with 50% probability displacement ellipsoids for non-H atoms.
Fig. 2.
The unusual S···π(Cp) interaction (dotted line) in (I). The red circle represents the centroid of the C21···C25 cyclopentadiene ring.
Fig. 3.
Crystal packing of (I) viewed down the c axis.

Crystal data

[FeCo2(C5H5)2(C3H3S3)S(C18H15P)(CO)]CF3SO3F000 = 1840
Mr = 910.53Dx = 1.750 Mg m3
Monoclinic, P21/cMo Kα radiation λ = 0.71073 Å
Hall symbol: -P 2ybcCell parameters from 5433 reflections
a = 11.0403 (6) Åθ = 2.3–23.6º
b = 29.2183 (14) ŵ = 1.77 mm1
c = 10.9040 (5) ÅT = 91 (2) K
β = 100.664 (3)ºIrregular fragment, black
V = 3456.7 (3) Å30.18 × 0.06 × 0.06 mm
Z = 4

Data collection

Bruker APEXII CCD area-detector diffractometer5502 independent reflections
Radiation source: fine-focus sealed tube4297 reflections with I > 2σ(I)
Monochromator: graphiteRint = 0.081
T = 91(2) Kθmax = 24.2º
ω scansθmin = 2.0º
Absorption correction: multi-scan(SADABS; Bruker, 2006)h = −12→12
Tmin = 0.717, Tmax = 0.899k = −33→33
36119 measured reflectionsl = −12→12

Refinement

Refinement on F2Secondary atom site location: difference Fourier map
Least-squares matrix: fullHydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.031H-atom parameters constrained
wR(F2) = 0.067  w = 1/[σ2(Fo2) + (0.0227P)2 + 1.9058P] where P = (Fo2 + 2Fc2)/3
S = 1.03(Δ/σ)max = 0.002
5502 reflectionsΔρmax = 0.38 e Å3
443 parametersΔρmin = −0.35 e Å3
Primary atom site location: structure-invariant direct methodsExtinction correction: none

Special details

Geometry. All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell e.s.d.'s are taken into account individually in the estimation of e.s.d.'s in distances, angles and torsion angles; correlations between e.s.d.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell e.s.d.'s is used for estimating e.s.d.'s involving l.s. planes.
Refinement. Refinement of F2 against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F2, conventional R-factors R are based on F, with F set to zero for negative F2. The threshold expression of F2 > σ(F2) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F2 are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger.

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

xyzUiso*/Ueq
S10.43507 (7)0.68025 (3)0.84869 (8)0.01321 (19)
Fe10.38034 (4)0.614761 (15)0.75881 (4)0.01093 (12)
Co10.59348 (4)0.647577 (15)0.79713 (4)0.01244 (12)
Co20.43989 (4)0.690431 (15)0.65645 (4)0.01123 (11)
C10.4900 (3)0.62912 (11)0.6502 (3)0.0119 (7)
S20.52197 (7)0.59798 (3)0.52361 (8)0.01445 (19)
C20.3965 (3)0.56308 (11)0.5050 (3)0.0126 (7)
S30.36348 (8)0.52579 (3)0.38030 (8)0.0195 (2)
C30.4831 (3)0.53630 (12)0.2912 (3)0.0219 (8)
H3A0.48770.56920.27470.033*
H3B0.46420.51970.21190.033*
H3C0.56240.52580.33860.033*
S40.29960 (7)0.56474 (3)0.60791 (8)0.0158 (2)
C40.4330 (3)0.57269 (12)0.8704 (3)0.0169 (8)
O40.4722 (2)0.54557 (8)0.9446 (2)0.0268 (6)
C110.7657 (3)0.65135 (13)0.7521 (3)0.0218 (9)
H110.78220.65730.67120.026*
C120.7543 (3)0.68458 (12)0.8438 (3)0.0232 (9)
H120.76080.71680.83500.028*
C130.7314 (3)0.66107 (13)0.9513 (3)0.0242 (9)
H130.72090.67481.02760.029*
C140.7270 (3)0.61407 (13)0.9253 (3)0.0249 (9)
H140.71240.59050.98070.030*
C150.7481 (3)0.60788 (13)0.8022 (3)0.0249 (9)
H150.75010.57940.76060.030*
C210.4574 (3)0.71066 (11)0.4791 (3)0.0171 (8)
H210.48800.69200.42020.021*
C220.3330 (3)0.71431 (11)0.4931 (3)0.0166 (8)
H220.26530.69880.44410.020*
C230.3258 (3)0.74476 (11)0.5918 (3)0.0173 (8)
H230.25340.75290.62240.021*
C240.4474 (3)0.76111 (11)0.6372 (3)0.0187 (8)
H240.47030.78270.70260.022*
C250.5283 (3)0.73976 (11)0.5685 (3)0.0192 (8)
H250.61490.74420.58020.023*
P10.19319 (7)0.62119 (3)0.81383 (8)0.01130 (19)
C310.1058 (3)0.66800 (11)0.7289 (3)0.0118 (7)
C320.0804 (3)0.66594 (11)0.5986 (3)0.0150 (8)
H320.10910.64070.55720.018*
C330.0139 (3)0.70032 (12)0.5291 (3)0.0185 (8)
H33−0.00510.69800.44080.022*
C34−0.0247 (3)0.73794 (12)0.5880 (3)0.0205 (8)
H34−0.07110.76140.54050.025*
C350.0044 (3)0.74128 (11)0.7162 (3)0.0192 (8)
H35−0.01990.76760.75670.023*
C360.0686 (3)0.70657 (11)0.7865 (3)0.0159 (8)
H360.08730.70920.87490.019*
C410.1856 (3)0.63076 (11)0.9778 (3)0.0130 (7)
C420.0678 (3)0.63315 (11)1.0099 (3)0.0138 (7)
H42−0.00360.63170.94630.017*
C430.0553 (3)0.63756 (11)1.1325 (3)0.0170 (8)
H43−0.02440.63991.15310.020*
C440.1591 (3)0.63864 (11)1.2259 (3)0.0157 (8)
H440.15020.64071.31070.019*
C450.2758 (3)0.63666 (11)1.1963 (3)0.0153 (8)
H450.34670.63781.26060.018*
C460.2888 (3)0.63291 (11)1.0721 (3)0.0131 (7)
H460.36880.63181.05180.016*
C510.0968 (3)0.56975 (11)0.7843 (3)0.0135 (7)
C520.0065 (3)0.56312 (12)0.6782 (3)0.0196 (8)
H52−0.01160.58690.61830.024*
C53−0.0570 (3)0.52218 (12)0.6594 (3)0.0241 (9)
H53−0.11730.51780.58600.029*
C54−0.0332 (3)0.48759 (12)0.7471 (4)0.0254 (9)
H54−0.07780.45970.73430.030*
C550.0555 (3)0.49360 (12)0.8532 (3)0.0239 (9)
H550.07130.47010.91420.029*
C560.1210 (3)0.53417 (11)0.8701 (3)0.0189 (8)
H560.18390.53780.94170.023*
S50.71566 (8)0.65888 (3)0.32134 (8)0.0176 (2)
O10.7829 (2)0.68745 (8)0.2496 (2)0.0249 (6)
O20.59310 (19)0.64632 (8)0.2590 (2)0.0201 (6)
O30.7252 (2)0.67193 (9)0.4504 (2)0.0260 (6)
C600.7989 (3)0.60449 (13)0.3295 (3)0.0221 (8)
F10.78346 (19)0.58458 (7)0.21758 (19)0.0351 (6)
F20.92021 (16)0.61032 (7)0.36923 (18)0.0264 (5)
F30.76096 (18)0.57506 (7)0.4081 (2)0.0321 (5)

Atomic displacement parameters (Å2)

U11U22U33U12U13U23
S10.0146 (4)0.0129 (5)0.0127 (4)−0.0008 (3)0.0039 (3)−0.0018 (3)
Fe10.0111 (3)0.0106 (3)0.0116 (3)−0.0004 (2)0.00340 (19)0.0001 (2)
Co10.0102 (2)0.0157 (3)0.0112 (2)−0.00022 (19)0.00134 (18)−0.00025 (19)
Co20.0121 (2)0.0103 (2)0.0113 (2)−0.00045 (19)0.00221 (18)0.00090 (19)
C10.0094 (17)0.0112 (18)0.0156 (18)0.0009 (13)0.0038 (14)0.0007 (14)
S20.0156 (4)0.0144 (5)0.0144 (4)−0.0022 (4)0.0057 (4)−0.0032 (3)
C20.0123 (17)0.0109 (18)0.0148 (18)0.0048 (14)0.0035 (14)0.0019 (14)
S30.0193 (5)0.0198 (5)0.0198 (5)−0.0038 (4)0.0044 (4)−0.0074 (4)
C30.024 (2)0.025 (2)0.017 (2)0.0017 (16)0.0063 (16)−0.0051 (16)
S40.0140 (4)0.0157 (5)0.0188 (5)−0.0029 (4)0.0055 (4)−0.0033 (4)
C40.0149 (19)0.019 (2)0.019 (2)0.0005 (15)0.0081 (15)−0.0054 (17)
O40.0319 (15)0.0215 (15)0.0268 (15)0.0092 (12)0.0052 (12)0.0096 (12)
C110.0101 (18)0.043 (3)0.0125 (19)−0.0021 (16)0.0019 (14)0.0019 (17)
C120.0089 (18)0.024 (2)0.034 (2)−0.0051 (15)−0.0029 (16)0.0023 (18)
C130.0138 (19)0.044 (3)0.0131 (19)0.0004 (17)−0.0028 (15)−0.0050 (17)
C140.0151 (19)0.033 (2)0.023 (2)0.0009 (17)−0.0054 (16)0.0120 (17)
C150.0099 (18)0.033 (2)0.030 (2)0.0071 (16)−0.0024 (16)−0.0062 (18)
C210.024 (2)0.0151 (19)0.0141 (19)0.0052 (15)0.0093 (15)0.0054 (15)
C220.0197 (19)0.0156 (19)0.0129 (18)0.0019 (15)−0.0014 (15)0.0047 (15)
C230.0200 (19)0.0093 (18)0.023 (2)0.0055 (15)0.0046 (15)0.0030 (15)
C240.026 (2)0.0075 (18)0.020 (2)0.0002 (15)−0.0021 (16)0.0012 (14)
C250.0144 (18)0.018 (2)0.025 (2)−0.0035 (15)0.0024 (15)0.0113 (16)
P10.0109 (4)0.0114 (5)0.0117 (5)−0.0007 (4)0.0025 (3)−0.0005 (4)
C310.0084 (17)0.0115 (18)0.0165 (19)−0.0022 (14)0.0050 (14)0.0015 (14)
C320.0137 (18)0.0134 (18)0.0170 (19)−0.0028 (14)0.0005 (15)−0.0010 (15)
C330.0173 (19)0.023 (2)0.0133 (18)−0.0009 (16)−0.0017 (15)0.0038 (15)
C340.0126 (18)0.024 (2)0.024 (2)0.0012 (15)−0.0001 (15)0.0086 (16)
C350.0207 (19)0.0122 (19)0.026 (2)0.0035 (15)0.0072 (16)−0.0013 (16)
C360.0184 (19)0.0155 (19)0.0151 (18)−0.0010 (15)0.0066 (15)−0.0001 (15)
C410.0133 (18)0.0101 (18)0.0168 (18)−0.0008 (14)0.0057 (14)0.0011 (14)
C420.0125 (18)0.0143 (19)0.0138 (18)−0.0005 (14)0.0004 (14)−0.0007 (14)
C430.0180 (19)0.0154 (19)0.021 (2)−0.0017 (15)0.0115 (16)0.0017 (15)
C440.024 (2)0.0146 (19)0.0096 (17)−0.0041 (15)0.0059 (15)−0.0016 (14)
C450.0166 (19)0.0146 (19)0.0132 (18)−0.0028 (15)−0.0012 (15)0.0022 (14)
C460.0118 (17)0.0112 (18)0.0177 (19)−0.0010 (14)0.0059 (14)−0.0019 (14)
C510.0084 (17)0.0157 (19)0.0188 (19)0.0009 (14)0.0088 (14)−0.0008 (15)
C520.0192 (19)0.018 (2)0.021 (2)−0.0019 (16)0.0028 (15)0.0031 (16)
C530.0167 (19)0.024 (2)0.030 (2)−0.0065 (16)−0.0004 (16)−0.0021 (18)
C540.022 (2)0.016 (2)0.040 (2)−0.0047 (16)0.0102 (18)−0.0036 (18)
C550.025 (2)0.017 (2)0.030 (2)0.0007 (16)0.0063 (17)0.0038 (17)
C560.0191 (19)0.017 (2)0.021 (2)−0.0005 (16)0.0035 (15)0.0013 (16)
S50.0152 (5)0.0214 (5)0.0160 (5)−0.0011 (4)0.0028 (4)0.0013 (4)
O10.0238 (14)0.0281 (15)0.0232 (14)−0.0080 (11)0.0052 (11)0.0041 (11)
O20.0150 (13)0.0223 (14)0.0216 (14)−0.0027 (10)−0.0005 (10)0.0039 (11)
O30.0248 (14)0.0368 (16)0.0171 (14)0.0012 (12)0.0054 (11)−0.0063 (12)
C600.015 (2)0.034 (2)0.018 (2)0.0016 (17)0.0050 (16)0.0002 (17)
F10.0359 (13)0.0377 (14)0.0288 (13)0.0105 (11)−0.0013 (10)−0.0149 (11)
F20.0148 (11)0.0381 (13)0.0267 (12)0.0016 (9)0.0046 (9)−0.0003 (10)
F30.0258 (12)0.0291 (13)0.0442 (14)0.0049 (10)0.0136 (10)0.0168 (11)

Geometric parameters (Å, °)

Co2—S12.1275 (9)C22—C231.410 (5)
Co1—S12.1564 (9)C22—H220.9500
Fe1—S12.1836 (9)C23—C241.425 (4)
Fe1—C41.751 (4)C23—H230.9500
Fe1—C11.891 (3)C24—C251.413 (5)
Fe1—S42.2572 (9)C24—H240.9500
Fe1—P12.2634 (10)C25—H250.9500
Fe1—Co12.5035 (6)P1—C311.824 (3)
Fe1—Co22.6149 (6)P1—C411.827 (3)
Co1—C11.867 (3)P1—C511.835 (3)
Co1—C112.052 (3)C31—C361.389 (4)
Co1—C152.056 (3)C31—C321.398 (4)
Co1—C122.060 (3)C32—C331.384 (4)
Co1—C142.079 (3)C32—H320.9500
Co1—C132.086 (3)C33—C341.380 (5)
Co1—Co22.4153 (6)C33—H330.9500
Co2—C11.880 (3)C34—C351.379 (5)
Co2—C212.065 (3)C34—H340.9500
Co2—C222.067 (3)C35—C361.385 (4)
Co2—C232.068 (3)C35—H350.9500
Co2—C252.073 (3)C36—H360.9500
Co2—C242.079 (3)C41—C461.388 (4)
C1—S21.743 (3)C41—C421.410 (4)
S2—C21.702 (3)C42—C431.375 (4)
S2—F33.198 (2)C42—H420.9500
S2—O33.317 (3)C43—C441.385 (4)
S2—S53.7879 (12)C43—H430.9500
S2—C604.032 (4)C44—C451.387 (4)
C2—S41.688 (3)C44—H440.9500
C2—S31.728 (3)C45—C461.392 (4)
S3—C31.805 (3)C45—H450.9500
C3—H3A0.9800C46—H460.9500
C3—H3B0.9800C51—C561.391 (4)
C3—H3C0.9800C51—C521.394 (4)
C4—O41.158 (4)C52—C531.382 (5)
C4—O4i4.040 (5)C52—H520.9500
O4—O4i2.941 (5)C53—C541.383 (5)
C11—C151.410 (5)C53—H530.9500
C11—C121.416 (5)C54—C551.382 (5)
C11—H110.9500C54—H540.9500
C12—C131.421 (5)C55—C561.383 (5)
C12—H120.9500C55—H550.9500
C13—C141.401 (5)C56—H560.9500
C13—H130.9500S5—O11.440 (2)
C14—C151.416 (5)S5—O31.443 (2)
C14—H140.9500S5—O21.445 (2)
C15—H150.9500S5—C601.829 (4)
C21—C221.414 (4)C60—F11.334 (4)
C21—C251.415 (5)C60—F31.335 (4)
C21—H210.9500C60—F21.340 (4)
Co2—S1—Co168.64 (3)C13—C12—Co170.94 (19)
Co2—S1—Fe174.67 (3)C11—C12—H12126.2
Co1—S1—Fe170.45 (3)C13—C12—H12126.2
C4—Fe1—C1114.96 (14)Co1—C12—H12124.9
C4—Fe1—S1105.94 (11)C14—C13—C12108.1 (3)
C1—Fe1—S186.02 (10)C14—C13—Co170.05 (19)
C4—Fe1—S495.02 (11)C12—C13—Co168.97 (19)
C1—Fe1—S484.22 (10)C14—C13—H13125.9
S1—Fe1—S4159.02 (4)C12—C13—H13125.9
C4—Fe1—P194.37 (11)Co1—C13—H13126.6
C1—Fe1—P1150.38 (10)C13—C14—C15108.2 (3)
S1—Fe1—P189.92 (3)C13—C14—Co170.6 (2)
S4—Fe1—P189.44 (3)C15—C14—Co169.12 (19)
C4—Fe1—Co188.38 (11)C13—C14—H14125.9
C1—Fe1—Co147.82 (9)C15—C14—H14125.9
S1—Fe1—Co154.27 (3)Co1—C14—H14125.9
S4—Fe1—Co1127.00 (3)C11—C15—C14108.1 (3)
P1—Fe1—Co1143.12 (3)C11—C15—Co169.8 (2)
C4—Fe1—Co2144.34 (11)C14—C15—Co170.84 (19)
C1—Fe1—Co245.92 (9)C11—C15—H15126.0
S1—Fe1—Co251.69 (3)C14—C15—H15126.0
S4—Fe1—Co2109.44 (3)Co1—C15—H15125.0
P1—Fe1—Co2110.91 (3)C22—C21—C25107.7 (3)
Co1—Fe1—Co256.263 (16)C22—C21—Co270.06 (18)
C1—Co1—C11104.89 (14)C25—C21—Co270.28 (19)
C1—Co1—C15103.48 (14)C22—C21—H21126.1
C11—Co1—C1540.14 (14)C25—C21—H21126.1
C1—Co1—C12136.54 (15)Co2—C21—H21125.1
C11—Co1—C1240.27 (14)C23—C22—C21108.9 (3)
C15—Co1—C1267.43 (14)C23—C22—Co270.08 (18)
C1—Co1—C14133.31 (14)C21—C22—Co269.91 (18)
C11—Co1—C1467.24 (14)C23—C22—H22125.6
C15—Co1—C1440.04 (14)C21—C22—H22125.6
C12—Co1—C1467.03 (14)Co2—C22—H22126.0
C1—Co1—C13170.24 (14)C22—C23—C24107.1 (3)
C11—Co1—C1367.19 (14)C22—C23—Co270.05 (18)
C15—Co1—C1366.83 (14)C24—C23—Co270.33 (18)
C12—Co1—C1340.08 (14)C22—C23—H23126.5
C14—Co1—C1339.32 (14)C24—C23—H23126.5
C1—Co1—S187.40 (10)Co2—C23—H23124.8
C11—Co1—S1150.50 (11)C25—C24—C23108.4 (3)
C15—Co1—S1162.20 (11)C25—C24—Co269.87 (19)
C12—Co1—S1114.00 (11)C23—C24—Co269.47 (18)
C14—Co1—S1122.79 (11)C25—C24—H24125.8
C13—Co1—S1102.27 (10)C23—C24—H24125.8
C1—Co1—Co250.10 (10)Co2—C24—H24126.4
C11—Co1—Co2113.13 (10)C24—C25—C21107.9 (3)
C15—Co1—Co2142.31 (11)C24—C25—Co270.35 (19)
C12—Co1—Co2110.88 (10)C21—C25—Co269.72 (19)
C14—Co1—Co2176.57 (11)C24—C25—H25126.0
C13—Co1—Co2137.37 (11)C21—C25—H25126.0
S1—Co1—Co255.12 (3)Co2—C25—H25125.5
C1—Co1—Fe148.64 (10)C31—P1—C41105.44 (15)
C11—Co1—Fe1149.80 (10)C31—P1—C51106.86 (14)
C15—Co1—Fe1122.58 (11)C41—P1—C5199.61 (15)
C12—Co1—Fe1169.27 (10)C31—P1—Fe1110.52 (11)
C14—Co1—Fe1117.35 (10)C41—P1—Fe1118.79 (11)
C13—Co1—Fe1136.90 (10)C51—P1—Fe1114.43 (11)
S1—Co1—Fe155.28 (3)C36—C31—C32118.3 (3)
Co2—Co1—Fe164.199 (18)C36—C31—P1123.5 (2)
C1—Co2—C2199.18 (14)C32—C31—P1118.1 (2)
C1—Co2—C22114.54 (13)C33—C32—C31120.8 (3)
C21—Co2—C2240.03 (12)C33—C32—H32119.6
C1—Co2—C23152.15 (13)C31—C32—H32119.6
C21—Co2—C2367.54 (13)C34—C33—C32120.1 (3)
C22—Co2—C2339.88 (13)C34—C33—H33119.9
C1—Co2—C25118.61 (14)C32—C33—H33119.9
C21—Co2—C2540.00 (13)C35—C34—C33119.6 (3)
C22—Co2—C2567.01 (13)C35—C34—H34120.2
C23—Co2—C2567.53 (13)C33—C34—H34120.2
C1—Co2—C24157.72 (14)C34—C35—C36120.6 (3)
C21—Co2—C2466.98 (14)C34—C35—H35119.7
C22—Co2—C2466.74 (13)C36—C35—H35119.7
C23—Co2—C2440.20 (12)C35—C36—C31120.5 (3)
C25—Co2—C2439.79 (13)C35—C36—H36119.7
C1—Co2—S187.93 (10)C31—C36—H36119.7
C21—Co2—S1170.52 (10)C46—C41—C42118.8 (3)
C22—Co2—S1141.40 (10)C46—C41—P1123.5 (2)
C23—Co2—S1108.56 (10)C42—C41—P1117.5 (2)
C25—Co2—S1130.76 (10)C43—C42—C41120.6 (3)
C24—Co2—S1104.29 (10)C43—C42—H42119.7
C1—Co2—Co149.63 (9)C41—C42—H42119.7
C21—Co2—Co1124.51 (9)C42—C43—C44119.9 (3)
C22—Co2—Co1160.72 (10)C42—C43—H43120.0
C23—Co2—Co1157.87 (9)C44—C43—H43120.0
C25—Co2—Co1108.60 (9)C43—C44—C45120.4 (3)
C24—Co2—Co1122.85 (9)C43—C44—H44119.8
S1—Co2—Co156.25 (3)C45—C44—H44119.8
C1—Co2—Fe146.27 (10)C44—C45—C46119.8 (3)
C21—Co2—Fe1135.74 (10)C44—C45—H45120.1
C22—Co2—Fe1120.30 (10)C46—C45—H45120.1
C23—Co2—Fe1127.53 (10)C41—C46—C45120.4 (3)
C25—Co2—Fe1164.27 (10)C41—C46—H46119.8
C24—Co2—Fe1154.27 (10)C45—C46—H46119.8
S1—Co2—Fe153.64 (3)C56—C51—C52118.2 (3)
Co1—Co2—Fe159.538 (17)C56—C51—P1117.4 (2)
S2—C1—Co1130.47 (17)C52—C51—P1124.2 (3)
S2—C1—Co2129.07 (18)C53—C52—C51120.6 (3)
Co1—C1—Co280.27 (13)C53—C52—H52119.7
S2—C1—Fe1128.84 (18)C51—C52—H52119.7
Co1—C1—Fe183.54 (13)C52—C53—C54120.2 (3)
Co2—C1—Fe187.81 (13)C52—C53—H53119.9
C2—S2—C197.32 (15)C54—C53—H53119.9
C2—S2—F3122.72 (12)C55—C54—C53120.1 (3)
C1—S2—F3136.38 (11)C55—C54—H54120.0
C2—S2—O3159.01 (12)C53—C54—H54120.0
C1—S2—O395.49 (11)C54—C55—C56119.5 (3)
F3—S2—O352.94 (6)C54—C55—H55120.3
C2—S2—S5138.33 (11)C56—C55—H55120.3
C1—S2—S5115.77 (11)C55—C56—C51121.4 (3)
C2—S2—C60130.20 (12)C55—C56—H56119.3
C1—S2—C60132.48 (12)C51—C56—H56119.3
S4—C2—S2120.38 (19)O1—S5—O3115.12 (15)
S4—C2—S3118.30 (18)O1—S5—O2115.05 (14)
S2—C2—S3121.31 (19)O3—S5—O2114.79 (14)
C2—S3—C3104.35 (16)O1—S5—C60103.03 (16)
S3—C3—H3A109.5O3—S5—C60103.68 (15)
S3—C3—H3B109.5O2—S5—C60102.73 (15)
H3A—C3—H3B109.5O1—S5—S2172.58 (11)
S3—C3—H3C109.5O3—S5—S260.23 (10)
H3A—C3—H3C109.5O2—S5—S264.80 (10)
H3B—C3—H3C109.5C60—S5—S284.03 (12)
C2—S4—Fe1106.84 (11)S5—O3—S297.59 (12)
O4—C4—Fe1177.4 (3)F1—C60—F3107.7 (3)
Fe1—C4—O4i165.73 (15)F1—C60—F2107.5 (3)
C4—O4—O4i158.3 (3)F3—C60—F2106.7 (3)
C15—C11—C12107.9 (3)F1—C60—S5110.9 (2)
C15—C11—Co170.08 (19)F3—C60—S5112.1 (2)
C12—C11—Co170.18 (19)F2—C60—S5111.6 (2)
C15—C11—H11126.0F1—C60—S2118.6 (2)
C12—C11—H11126.0F2—C60—S2130.3 (2)
Co1—C11—H11125.3S5—C60—S269.14 (10)
C11—C12—C13107.7 (3)C60—F3—S2119.84 (19)
C11—C12—Co169.55 (19)

Symmetry codes: (i) −x+1, −y+1, −z+2.

Hydrogen-bond geometry (Å, °)

D—H···AD—HH···AD···AD—H···A
C3—H3A···O20.982.563.477 (4)156
C3—H3C···F30.982.623.297 (4)127
C11—H11···O30.952.413.293 (4)154
C21—H21···O20.952.643.588 (4)174
C21—H21···O30.952.643.235 (4)121
C13—H13···O1ii0.952.423.288 (4)152
C14—H14···F1ii0.952.563.248 (4)129
C35—H35···O1iii0.952.533.283 (4)136
C24—H24···O2iv0.952.493.298 (4)143

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

Footnotes

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: HB2713).

References

  • Allen, F. H. (2002). Acta Cryst. B58, 380–388. [PubMed]
  • Allen, F. H., Johnson, O., Shields, G. P., Smith, B. R. & Towler, M. (2004). J. Appl. Cryst.37, 335–338.
  • Allen, F. H., Kennard, O., Watson, D. G., Brammer, L., Orpen, A. G. & Taylor, R. (1987). J. Chem. Soc. Perkin Trans. 2, pp. S1–S19.
  • Bruker (2006). APEX2, SAINT and SADABS Bruker AXS Inc., Madison, Wisconsin, USA.
  • Farrugia, L. J. (1997). J. Appl. Cryst.30, 565.
  • Hunter, K. A. & Simpson, J. (1999). TITAN2000 University of Otago, New Zealand.
  • Macrae, C. F., Edgington, P. R., McCabe, P., Pidcock, E., Shields, G. P., Taylor, R., Towler, M. & van de Streek, J. (2006). J. Appl. Cryst.39, 453–457.
  • Manning, A. R., McAdam, C. J., Palmer, A. J., Robinson, B. H. & Simpson, J. (2003). Dalton Trans. pp. 4472–4481.
  • Manning, A. R., O’Dwyer, L., McArdle, P. A. & Cunningham, D. (1995). J. Organomet. Chem.503, C46–C47.
  • Manning, A. R., O’Dwyer, L., McArdle, P. A. & Cunningham, D. (1998). J. Organomet. Chem.551, 139–149.
  • Manning, A. R., O’Dwyer, L., McArdle, P. A. & Cunningham, D. (1999). J. Organomet. Chem.573, 109–120.
  • Manning, A. R., Palmer, A. J., McAdam, C. J., Robinson, B. H. & Simpson, J. (1998). Chem. Commun. pp. 1577–1578.
  • Ringer, A. L., Senenko, A. & Sherrill, C. D. (2007). Protein Sci.16, 1–8.
  • Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. [PubMed]
  • Spek, A. L. (2003). J. Appl. Cryst.36, 7–13.

Articles from Acta Crystallographica Section E: Structure Reports Online are provided here courtesy of International Union of Crystallography