Aqua-carbon-yl(ferrocenyldi-thio-phos-phon-ato-κ(2) S,S')bis-(tri-phenyl-phosphane-κP)ruthenium(II) dichloromethane mono-solvate.

The structure of the title complex, [FeRu(C5H5)(C5H4OPS2)(CO)(C18H15P)2(H2O)]·CH2Cl2, consists of one neutral [{FcP(O)S2}Ru(CO)(H2O)(PPh3)2] complex [Fc = Fe(η(5)-C5H4)(η(5)-C5H5)] and one CH2Cl2 solvent mol-ecule. The geometry around the Ru(II) atom is pseudo-octa-hedral, with two cis-binding PPh3 ligands and one chelating bidentate [Fc(O)PS2](2-) ligand via two S atoms. The average Ru-S and Ru-P bond lengths are 2.434 (1) and 2.398 (1) Å, and the Ru-O and Ru-C bond lengths are 2.157 (3) and 1.826 (4) Å, respectively. In the crystal, pairs of O-H⋯O hydrogen bonds link adjacent mol-ecules into dimers.

Related literature

For background to ferrocen­yl–phosphono­dithiol­ato com­plexes, see: Foreman et al. (1996 ▶); Gray et al. (2003 ▶, 2004 ▶); Haiduc (2001 ▶); Thomas et al. (2001 ▶); Van Zyl (2010 ▶). For a related structure, see: Liu et al. (2005 ▶); Wang et al. (2010 ▶); Zhang et al. (2001 ▶). For a description of the Cambridge Structural Database, see: Allen (2002 ▶).

Experimental

Crystal data

[FeRu(C5H5)(C5H4OPS2)(CO)(C18H15P)2(H2O)]·CH2Cl2

M = 1052.67

Triclinic,

a = 12.1493 (9) Å

b = 14.2208 (11) Å

c = 14.7100 (11) Å

α = 101.811 (1)°

β = 98.278 (1)°

γ = 109.759 (1)°

V = 2277.7 (3) Å3

Z = 2

Mo Kα radiation

μ = 1.01 mm−1

T = 296 K

0.24 × 0.15 × 0.08 mm

Data collection

Bruker SMART APEXII CCD area-detector diffractometer

Absorption correction: multi-scan (SADABS; Sheldrick, 1997 ▶) T min = 0.794, T max = 0.924

32262 measured reflections

10536 independent reflections

8221 reflections with I > 2σ(I)

R int = 0.039

Refinement

R[F 2 > 2σ(F 2)] = 0.054

wR(F 2) = 0.154

S = 1.05

10536 reflections

549 parameters

2 restraints

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 3.98 e Å−3

Δρmin = −0.67 e Å−3

Data collection: APEX2 (Bruker, 2005 ▶); cell refinement: SAINT (Bruker, 2005 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: SHELXTL (Sheldrick, 2008 ▶); software used to prepare material for publication: SHELXTL.

Click here for additional data file.

Crystal structure: contains datablock(s) I, global. DOI: 10.1107/S1600536813014311/ds2231sup1.cif

Click here for additional data file.

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536813014311/ds2231Isup2.hkl

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

[FeRu(C5H5)(C5H4OPS2)(CO)(C18H15P)2(H2O)]·CH2Cl2	Z = 2
Mr = 1052.67	F(000) = 1072
Triclinic, P1	Dx = 1.535 Mg m−3
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 12.1493 (9) Å	Cell parameters from 6761 reflections
b = 14.2208 (11) Å	θ = 2.4–25.7°
c = 14.7100 (11) Å	µ = 1.01 mm−1
α = 101.811 (1)°	T = 296 K
β = 98.278 (1)°	Block, yellow
γ = 109.759 (1)°	0.24 × 0.15 × 0.08 mm
V = 2277.7 (3) Å3

Bruker SMART APEXII CCD area-detector diffractometer	10536 independent reflections
Radiation source: fine-focus sealed tube	8221 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.039
phi and ω scans	θmax = 27.6°, θmin = 2.4°
Absorption correction: multi-scan (SADABS; Sheldrick, 1997)	h = −15→15
Tmin = 0.794, Tmax = 0.924	k = −18→18
32262 measured reflections	l = −19→19

Refinement on F2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.054	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.154	H atoms treated by a mixture of independent and constrained refinement
S = 1.05	w = 1/[σ2(Fo2) + (0.0853P)2 + 2.0442P] where P = (Fo2 + 2Fc2)/3
10536 reflections	(Δ/σ)max = 0.001
549 parameters	Δρmax = 3.98 e Å−3
2 restraints	Δρmin = −0.67 e Å−3

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.

	x	y	z	Uiso*/Ueq
Ru1	0.57682 (3)	0.84933 (2)	0.60821 (2)	0.02666 (10)
Fe1	0.34922 (7)	0.55279 (5)	0.22580 (5)	0.04881 (18)
O3	0.5232 (3)	0.9764 (2)	0.5934 (2)	0.0406 (7)
H1S	0.541 (4)	1.0333 (16)	0.632 (2)	0.029 (11)*
H2S	0.460 (3)	0.962 (5)	0.555 (4)	0.09 (2)*
S1	0.40195 (9)	0.74574 (8)	0.47898 (7)	0.0361 (2)
S2	0.66350 (9)	0.87473 (8)	0.47088 (7)	0.0378 (2)
P1	0.49822 (9)	0.78762 (7)	0.38051 (7)	0.0305 (2)
P2	0.44859 (9)	0.80208 (7)	0.71339 (7)	0.0299 (2)
P3	0.76866 (9)	0.97232 (8)	0.70618 (7)	0.0306 (2)
O1	0.4530 (3)	0.8442 (2)	0.3179 (2)	0.0418 (7)
O2	0.6390 (3)	0.6647 (2)	0.6043 (3)	0.0588 (9)
C1	0.5005 (4)	0.6752 (3)	0.3034 (3)	0.0354 (8)
C2	0.5009 (5)	0.5821 (4)	0.3236 (3)	0.0514 (12)
H2	0.5042	0.5688	0.3831	0.062*
C3	0.4953 (5)	0.5126 (4)	0.2371 (4)	0.0593 (13)
H3	0.4951	0.4461	0.2304	0.071*
C4	0.4899 (5)	0.5611 (4)	0.1627 (4)	0.0629 (14)
H4	0.4848	0.5321	0.0988	0.075*
C5	0.4937 (5)	0.6615 (3)	0.2028 (3)	0.0495 (11)
H5	0.4920	0.7104	0.1698	0.059*
C6	0.2098 (7)	0.5002 (9)	0.2869 (7)	0.109 (3)
H6	0.2179	0.4986	0.3503	0.131*
C7	0.2044 (7)	0.4244 (6)	0.2133 (8)	0.107 (3)
H7	0.2062	0.3607	0.2183	0.128*
C8	0.1960 (6)	0.4522 (6)	0.1304 (6)	0.093 (2)
H8	0.1915	0.4117	0.0706	0.111*
C9	0.1952 (7)	0.5517 (8)	0.1503 (8)	0.114 (3)
H9	0.1916	0.5910	0.1074	0.136*
C10	0.2012 (6)	0.5817 (7)	0.2517 (8)	0.112 (3)
H10	0.1995	0.6435	0.2865	0.135*
C11	0.3794 (3)	0.8935 (3)	0.7572 (3)	0.0352 (8)
C12	0.3908 (4)	0.9360 (3)	0.8534 (3)	0.0473 (10)
H12	0.4339	0.9171	0.8991	0.057*
C13	0.3380 (5)	1.0067 (4)	0.8819 (4)	0.0642 (14)
H13	0.3455	1.0344	0.9466	0.077*
C14	0.2758 (5)	1.0353 (4)	0.8160 (5)	0.0689 (17)
H14	0.2415	1.0832	0.8356	0.083*
C15	0.2630 (5)	0.9939 (4)	0.7202 (5)	0.0608 (14)
H15	0.2199	1.0137	0.6753	0.073*
C16	0.3142 (4)	0.9226 (4)	0.6904 (4)	0.0479 (11)
H16	0.3048	0.8942	0.6255	0.058*
C20	0.6172 (3)	0.7368 (3)	0.6083 (3)	0.0349 (8)
C21	0.3166 (4)	0.6803 (3)	0.6583 (3)	0.0378 (9)
C22	0.3325 (4)	0.5913 (3)	0.6148 (3)	0.0485 (11)
H22	0.4094	0.5950	0.6103	0.058*
C23	0.2363 (5)	0.4970 (4)	0.5777 (4)	0.0632 (14)
H23	0.2485	0.4380	0.5483	0.076*
C24	0.1235 (5)	0.4914 (4)	0.5847 (5)	0.0755 (18)
H24	0.0585	0.4284	0.5593	0.091*
C25	0.1053 (5)	0.5774 (5)	0.6287 (5)	0.0790 (19)
H25	0.0285	0.5722	0.6349	0.095*
C26	0.2008 (4)	0.6723 (4)	0.6642 (4)	0.0592 (13)
H26	0.1874	0.7311	0.6922	0.071*
C31	0.5046 (4)	0.7699 (3)	0.8209 (3)	0.0344 (8)
C32	0.4262 (4)	0.7171 (3)	0.8702 (3)	0.0430 (10)
H32	0.3440	0.6993	0.8496	0.052*
C33	0.4688 (5)	0.6907 (4)	0.9492 (3)	0.0532 (12)
H33	0.4154	0.6559	0.9818	0.064*
C34	0.5900 (5)	0.7156 (4)	0.9800 (3)	0.0547 (12)
H34	0.6187	0.6975	1.0332	0.066*
C35	0.6690 (5)	0.7675 (4)	0.9317 (3)	0.0531 (12)
H35	0.7511	0.7843	0.9522	0.064*
C36	0.6264 (4)	0.7946 (3)	0.8530 (3)	0.0420 (9)
H36	0.6803	0.8300	0.8210	0.050*
C41	0.8587 (3)	1.0592 (3)	0.6437 (3)	0.0332 (8)
C42	0.8153 (4)	1.1299 (3)	0.6144 (3)	0.0447 (10)
H42	0.7427	1.1315	0.6262	0.054*
C43	0.8791 (4)	1.1975 (3)	0.5681 (4)	0.0500 (11)
H43	0.8490	1.2441	0.5485	0.060*
C44	0.9874 (5)	1.1962 (4)	0.5508 (4)	0.0587 (13)
H44	1.0303	1.2416	0.5194	0.070*
C45	1.0315 (5)	1.1275 (4)	0.5800 (5)	0.0682 (16)
H45	1.1048	1.1270	0.5691	0.082*
C46	0.9668 (5)	1.0587 (4)	0.6261 (4)	0.0563 (13)
H46	0.9969	1.0120	0.6452	0.068*
C51	0.8706 (3)	0.9121 (3)	0.7488 (3)	0.0367 (9)
C52	0.8946 (4)	0.8419 (3)	0.6820 (3)	0.0413 (9)
H52	0.8600	0.8274	0.6175	0.050*
C53	0.9693 (4)	0.7934 (4)	0.7102 (4)	0.0519 (12)
H53	0.9858	0.7475	0.6646	0.062*
C54	1.0187 (5)	0.8123 (4)	0.8038 (4)	0.0593 (13)
H54	1.0689	0.7793	0.8223	0.071*
C55	0.9948 (5)	0.8805 (4)	0.8720 (4)	0.0607 (14)
H55	1.0275	0.8923	0.9364	0.073*
C56	0.9218 (4)	0.9312 (4)	0.8444 (3)	0.0490 (11)
H56	0.9072	0.9782	0.8902	0.059*
C61	0.7790 (4)	1.0714 (3)	0.8121 (3)	0.0356 (8)
C62	0.6762 (4)	1.0715 (3)	0.8422 (3)	0.0453 (10)
H62	0.6019	1.0203	0.8094	0.054*
C63	0.6843 (5)	1.1488 (4)	0.9222 (4)	0.0610 (14)
H63	0.6154	1.1477	0.9432	0.073*
C64	0.7919 (5)	1.2250 (4)	0.9693 (4)	0.0605 (14)
H64	0.7963	1.2762	1.0219	0.073*
C65	0.8950 (5)	1.2269 (4)	0.9395 (4)	0.0604 (13)
H65	0.9688	1.2789	0.9725	0.072*
C66	0.8888 (4)	1.1513 (4)	0.8603 (3)	0.0508 (11)
H66	0.9581	1.1540	0.8392	0.061*
C1S	0.8456 (18)	0.6112 (13)	0.2091 (9)	0.264 (11)
H1S1	0.7820	0.5791	0.2390	0.317*
H1S2	0.9174	0.6505	0.2597	0.317*
Cl1S	0.8099 (3)	0.6917 (4)	0.1639 (4)	0.2144 (19)
Cl2S	0.8735 (4)	0.5084 (4)	0.1346 (4)	0.2133 (17)

	U11	U22	U33	U12	U13	U23
Ru1	0.02830 (16)	0.02926 (16)	0.02479 (16)	0.01314 (12)	0.00753 (12)	0.00756 (11)
Fe1	0.0577 (4)	0.0377 (3)	0.0416 (4)	0.0124 (3)	0.0055 (3)	0.0049 (3)
O3	0.0535 (19)	0.0318 (15)	0.0399 (17)	0.0233 (14)	0.0068 (15)	0.0077 (13)
S1	0.0323 (5)	0.0421 (5)	0.0291 (5)	0.0102 (4)	0.0071 (4)	0.0061 (4)
S2	0.0344 (5)	0.0441 (5)	0.0301 (5)	0.0086 (4)	0.0113 (4)	0.0077 (4)
P1	0.0372 (5)	0.0279 (4)	0.0271 (5)	0.0140 (4)	0.0073 (4)	0.0060 (4)
P2	0.0315 (5)	0.0345 (5)	0.0289 (5)	0.0156 (4)	0.0109 (4)	0.0116 (4)
P3	0.0287 (5)	0.0366 (5)	0.0280 (5)	0.0145 (4)	0.0065 (4)	0.0087 (4)
O1	0.0580 (19)	0.0330 (14)	0.0340 (15)	0.0203 (13)	0.0051 (13)	0.0071 (12)
O2	0.055 (2)	0.0425 (17)	0.087 (3)	0.0301 (16)	0.0137 (19)	0.0167 (17)
C1	0.040 (2)	0.0319 (19)	0.033 (2)	0.0151 (16)	0.0078 (17)	0.0031 (15)
C2	0.072 (3)	0.048 (2)	0.046 (3)	0.037 (2)	0.012 (2)	0.015 (2)
C3	0.083 (4)	0.042 (2)	0.058 (3)	0.035 (3)	0.018 (3)	0.004 (2)
C4	0.087 (4)	0.048 (3)	0.048 (3)	0.024 (3)	0.029 (3)	−0.002 (2)
C5	0.067 (3)	0.041 (2)	0.039 (2)	0.018 (2)	0.021 (2)	0.0084 (19)
C6	0.061 (4)	0.141 (8)	0.102 (7)	0.005 (5)	0.030 (4)	0.033 (6)
C7	0.084 (5)	0.066 (4)	0.134 (8)	−0.008 (4)	0.017 (5)	0.021 (5)
C8	0.077 (5)	0.082 (5)	0.078 (5)	0.016 (4)	−0.013 (4)	−0.019 (4)
C9	0.073 (5)	0.122 (7)	0.142 (8)	0.034 (5)	−0.019 (5)	0.065 (6)
C10	0.044 (3)	0.105 (6)	0.143 (8)	0.024 (4)	0.002 (4)	−0.038 (6)
C11	0.0313 (19)	0.0363 (19)	0.043 (2)	0.0152 (16)	0.0177 (17)	0.0122 (17)
C12	0.049 (3)	0.049 (2)	0.046 (3)	0.023 (2)	0.016 (2)	0.006 (2)
C13	0.067 (3)	0.055 (3)	0.073 (4)	0.032 (3)	0.027 (3)	0.001 (3)
C14	0.065 (3)	0.047 (3)	0.114 (5)	0.037 (3)	0.042 (4)	0.021 (3)
C15	0.054 (3)	0.067 (3)	0.092 (4)	0.040 (3)	0.034 (3)	0.046 (3)
C16	0.046 (3)	0.055 (3)	0.057 (3)	0.027 (2)	0.022 (2)	0.027 (2)
C20	0.0305 (19)	0.0347 (19)	0.038 (2)	0.0132 (16)	0.0042 (17)	0.0090 (16)
C21	0.039 (2)	0.039 (2)	0.034 (2)	0.0123 (17)	0.0093 (17)	0.0130 (17)
C22	0.051 (3)	0.042 (2)	0.053 (3)	0.017 (2)	0.016 (2)	0.013 (2)
C23	0.071 (4)	0.034 (2)	0.070 (4)	0.011 (2)	0.006 (3)	0.007 (2)
C24	0.056 (3)	0.044 (3)	0.102 (5)	0.001 (2)	−0.006 (3)	0.014 (3)
C25	0.038 (3)	0.059 (3)	0.125 (6)	0.009 (2)	0.009 (3)	0.017 (4)
C26	0.043 (3)	0.049 (3)	0.083 (4)	0.016 (2)	0.012 (3)	0.014 (3)
C31	0.045 (2)	0.0371 (19)	0.0268 (19)	0.0196 (17)	0.0129 (17)	0.0112 (15)
C32	0.051 (3)	0.053 (2)	0.034 (2)	0.023 (2)	0.020 (2)	0.0179 (19)
C33	0.076 (4)	0.054 (3)	0.041 (3)	0.028 (3)	0.028 (2)	0.024 (2)
C34	0.078 (4)	0.060 (3)	0.036 (2)	0.034 (3)	0.011 (2)	0.021 (2)
C35	0.054 (3)	0.066 (3)	0.045 (3)	0.028 (2)	0.007 (2)	0.022 (2)
C36	0.043 (2)	0.051 (2)	0.036 (2)	0.0176 (19)	0.0098 (19)	0.0195 (19)
C41	0.0304 (19)	0.0360 (19)	0.032 (2)	0.0111 (15)	0.0083 (16)	0.0085 (16)
C42	0.039 (2)	0.048 (2)	0.054 (3)	0.0187 (19)	0.013 (2)	0.021 (2)
C43	0.053 (3)	0.042 (2)	0.058 (3)	0.017 (2)	0.013 (2)	0.021 (2)
C44	0.074 (4)	0.047 (3)	0.063 (3)	0.018 (2)	0.037 (3)	0.023 (2)
C45	0.065 (3)	0.066 (3)	0.106 (5)	0.037 (3)	0.058 (3)	0.042 (3)
C46	0.054 (3)	0.056 (3)	0.082 (4)	0.032 (2)	0.036 (3)	0.036 (3)
C51	0.032 (2)	0.045 (2)	0.040 (2)	0.0177 (17)	0.0098 (17)	0.0185 (18)
C52	0.038 (2)	0.049 (2)	0.042 (2)	0.0217 (19)	0.0088 (19)	0.0153 (19)
C53	0.045 (3)	0.058 (3)	0.066 (3)	0.031 (2)	0.019 (2)	0.023 (2)
C54	0.050 (3)	0.069 (3)	0.075 (4)	0.035 (3)	0.012 (3)	0.036 (3)
C55	0.055 (3)	0.079 (4)	0.050 (3)	0.028 (3)	−0.002 (2)	0.029 (3)
C56	0.049 (3)	0.062 (3)	0.041 (2)	0.027 (2)	0.005 (2)	0.018 (2)
C61	0.042 (2)	0.038 (2)	0.0287 (19)	0.0179 (17)	0.0078 (17)	0.0077 (16)
C62	0.046 (2)	0.044 (2)	0.043 (2)	0.0159 (19)	0.015 (2)	0.0040 (19)
C63	0.067 (3)	0.059 (3)	0.057 (3)	0.024 (3)	0.031 (3)	0.002 (2)
C64	0.084 (4)	0.053 (3)	0.041 (3)	0.029 (3)	0.012 (3)	0.001 (2)
C65	0.059 (3)	0.053 (3)	0.048 (3)	0.010 (2)	−0.004 (2)	0.000 (2)
C66	0.041 (2)	0.052 (3)	0.046 (3)	0.011 (2)	0.004 (2)	0.000 (2)
C1S	0.42 (3)	0.192 (14)	0.090 (9)	0.012 (16)	−0.011 (12)	0.071 (10)
Cl1S	0.0880 (19)	0.266 (5)	0.281 (5)	0.041 (2)	0.017 (2)	0.122 (4)
Cl2S	0.175 (3)	0.190 (4)	0.221 (4)	0.019 (3)	0.041 (3)	0.034 (3)

Ru1—C20	1.826 (4)	C21—C22	1.385 (6)
Ru1—O3	2.157 (3)	C21—C26	1.389 (6)
Ru1—P2	2.3842 (10)	C22—C23	1.385 (7)
Ru1—P3	2.4110 (10)	C22—H22	0.9300
Ru1—S1	2.4232 (10)	C23—C24	1.366 (8)
Ru1—S2	2.4443 (10)	C23—H23	0.9300
Fe1—C7	2.015 (7)	C24—C25	1.365 (8)
Fe1—C6	2.023 (7)	C24—H24	0.9300
Fe1—C9	2.027 (7)	C25—C26	1.386 (7)
Fe1—C8	2.027 (6)	C25—H25	0.9300
Fe1—C2	2.028 (5)	C26—H26	0.9300
Fe1—C1	2.033 (4)	C31—C36	1.384 (6)
Fe1—C5	2.033 (5)	C31—C32	1.392 (6)
Fe1—C3	2.035 (5)	C32—C33	1.376 (6)
Fe1—C4	2.040 (5)	C32—H32	0.9300
Fe1—C10	2.045 (7)	C33—C34	1.374 (8)
O3—H1S	0.824 (10)	C33—H33	0.9300
O3—H2S	0.818 (10)	C34—C35	1.380 (7)
S1—P1	2.0472 (14)	C34—H34	0.9300
S2—P1	2.0517 (14)	C35—C36	1.379 (6)
P1—O1	1.502 (3)	C35—H35	0.9300
P1—C1	1.772 (4)	C36—H36	0.9300
P2—C11	1.834 (4)	C41—C46	1.376 (6)
P2—C31	1.836 (4)	C41—C42	1.394 (5)
P2—C21	1.844 (4)	C42—C43	1.381 (6)
P3—C61	1.831 (4)	C42—H42	0.9300
P3—C51	1.837 (4)	C43—C44	1.381 (7)
P3—C41	1.846 (4)	C43—H43	0.9300
O2—C20	1.136 (5)	C44—C45	1.373 (7)
C1—C2	1.417 (6)	C44—H44	0.9300
C1—C5	1.439 (6)	C45—C46	1.393 (7)
C2—C3	1.421 (6)	C45—H45	0.9300
C2—H2	0.9300	C46—H46	0.9300
C3—C4	1.412 (7)	C51—C56	1.384 (6)
C3—H3	0.9300	C51—C52	1.388 (6)
C4—C5	1.410 (6)	C52—C53	1.379 (6)
C4—H4	0.9300	C52—H52	0.9300
C5—H5	0.9300	C53—C54	1.354 (7)
C6—C7	1.339 (12)	C53—H53	0.9300
C6—C10	1.391 (12)	C54—C55	1.381 (8)
C6—H6	0.9300	C54—H54	0.9300
C7—C8	1.358 (11)	C55—C56	1.385 (6)
C7—H7	0.9300	C55—H55	0.9300
C8—C9	1.388 (11)	C56—H56	0.9300
C8—H8	0.9300	C61—C62	1.384 (6)
C9—C10	1.449 (12)	C61—C66	1.395 (6)
C9—H9	0.9300	C62—C63	1.403 (6)
C10—H10	0.9300	C62—H62	0.9300
C11—C12	1.387 (6)	C63—C64	1.355 (8)
C11—C16	1.388 (6)	C63—H63	0.9300
C12—C13	1.393 (6)	C64—C65	1.379 (8)
C12—H12	0.9300	C64—H64	0.9300
C13—C14	1.355 (8)	C65—C66	1.387 (7)
C13—H13	0.9300	C65—H65	0.9300
C14—C15	1.376 (8)	C66—H66	0.9300
C14—H14	0.9300	C1S—Cl1S	1.582 (16)
C15—C16	1.391 (6)	C1S—Cl2S	1.80 (2)
C15—H15	0.9300	C1S—H1S1	0.9700
C16—H16	0.9300	C1S—H1S2	0.9700
C20—Ru1—O3	174.49 (15)	C9—C8—H8	125.9
C20—Ru1—P2	90.26 (13)	Fe1—C8—H8	125.7
O3—Ru1—P2	92.66 (9)	C8—C9—C10	105.8 (8)
C20—Ru1—P3	94.08 (12)	C8—C9—Fe1	70.0 (4)
O3—Ru1—P3	89.54 (9)	C10—C9—Fe1	69.8 (4)
P2—Ru1—P3	106.97 (4)	C8—C9—H9	127.1
C20—Ru1—S1	91.03 (13)	C10—C9—H9	127.1
O3—Ru1—S1	84.48 (9)	Fe1—C9—H9	124.7
P2—Ru1—S1	86.51 (4)	C6—C10—C9	106.7 (7)
P3—Ru1—S1	165.53 (4)	C6—C10—Fe1	69.1 (4)
C20—Ru1—S2	90.95 (13)	C9—C10—Fe1	68.5 (4)
O3—Ru1—S2	85.10 (9)	C6—C10—H10	126.7
P2—Ru1—S2	166.20 (4)	C9—C10—H10	126.7
P3—Ru1—S2	86.65 (3)	Fe1—C10—H10	127.3
S1—Ru1—S2	79.73 (4)	C12—C11—C16	118.7 (4)
C7—Fe1—C6	38.7 (3)	C12—C11—P2	123.2 (3)
C7—Fe1—C9	66.7 (4)	C16—C11—P2	118.0 (3)
C6—Fe1—C9	68.5 (4)	C11—C12—C13	120.3 (5)
C7—Fe1—C8	39.3 (3)	C11—C12—H12	119.8
C6—Fe1—C8	66.7 (4)	C13—C12—H12	119.8
C9—Fe1—C8	40.0 (3)	C14—C13—C12	120.3 (5)
C7—Fe1—C2	118.0 (3)	C14—C13—H13	119.8
C6—Fe1—C2	106.7 (3)	C12—C13—H13	119.8
C9—Fe1—C2	166.5 (4)	C13—C14—C15	120.3 (5)
C8—Fe1—C2	151.0 (3)	C13—C14—H14	119.8
C7—Fe1—C1	152.2 (3)	C15—C14—H14	119.8
C6—Fe1—C1	119.6 (3)	C14—C15—C16	120.1 (5)
C9—Fe1—C1	129.5 (3)	C14—C15—H15	119.9
C8—Fe1—C1	167.3 (3)	C16—C15—H15	119.9
C2—Fe1—C1	40.84 (17)	C11—C16—C15	120.1 (5)
C7—Fe1—C5	164.7 (3)	C11—C16—H16	119.9
C6—Fe1—C5	155.7 (4)	C15—C16—H16	119.9
C9—Fe1—C5	109.9 (3)	O2—C20—Ru1	176.9 (4)
C8—Fe1—C5	128.6 (3)	C22—C21—C26	118.0 (4)
C2—Fe1—C5	69.0 (2)	C22—C21—P2	119.7 (3)
C1—Fe1—C5	41.46 (17)	C26—C21—P2	122.2 (3)
C7—Fe1—C3	107.4 (3)	C23—C22—C21	121.4 (5)
C6—Fe1—C3	125.1 (4)	C23—C22—H22	119.3
C9—Fe1—C3	152.2 (4)	C21—C22—H22	119.3
C8—Fe1—C3	117.9 (3)	C24—C23—C22	119.4 (5)
C2—Fe1—C3	40.93 (19)	C24—C23—H23	120.3
C1—Fe1—C3	68.67 (18)	C22—C23—H23	120.3
C5—Fe1—C3	68.2 (2)	C23—C24—C25	120.6 (5)
C7—Fe1—C4	126.8 (3)	C23—C24—H24	119.7
C6—Fe1—C4	162.2 (4)	C25—C24—H24	119.7
C9—Fe1—C4	119.5 (4)	C24—C25—C26	120.2 (5)
C8—Fe1—C4	108.2 (3)	C24—C25—H25	119.9
C2—Fe1—C4	69.0 (2)	C26—C25—H25	119.9
C1—Fe1—C4	69.13 (18)	C25—C26—C21	120.4 (5)
C5—Fe1—C4	40.51 (18)	C25—C26—H26	119.8
C3—Fe1—C4	40.6 (2)	C21—C26—H26	119.8
C7—Fe1—C10	65.9 (4)	C36—C31—C32	118.2 (4)
C6—Fe1—C10	40.0 (4)	C36—C31—P2	120.5 (3)
C9—Fe1—C10	41.7 (4)	C32—C31—P2	121.2 (3)
C8—Fe1—C10	67.5 (3)	C33—C32—C31	120.9 (5)
C2—Fe1—C10	126.7 (3)	C33—C32—H32	119.6
C1—Fe1—C10	109.5 (2)	C31—C32—H32	119.6
C5—Fe1—C10	122.4 (3)	C34—C33—C32	120.2 (5)
C3—Fe1—C10	163.0 (4)	C34—C33—H33	119.9
C4—Fe1—C10	156.0 (4)	C32—C33—H33	119.9
Ru1—O3—H1S	130 (3)	C33—C34—C35	119.8 (4)
Ru1—O3—H2S	116 (5)	C33—C34—H34	120.1
H1S—O3—H2S	110 (5)	C35—C34—H34	120.1
P1—S1—Ru1	90.85 (5)	C36—C35—C34	120.1 (5)
P1—S2—Ru1	90.15 (4)	C36—C35—H35	120.0
O1—P1—C1	106.63 (18)	C34—C35—H35	120.0
O1—P1—S1	116.18 (13)	C35—C36—C31	120.9 (4)
C1—P1—S1	109.51 (14)	C35—C36—H36	119.5
O1—P1—S2	114.15 (13)	C31—C36—H36	119.5
C1—P1—S2	111.17 (14)	C46—C41—C42	118.7 (4)
S1—P1—S2	99.14 (6)	C46—C41—P3	123.4 (3)
C11—P2—C31	103.93 (18)	C42—C41—P3	117.9 (3)
C11—P2—C21	102.26 (19)	C43—C42—C41	120.7 (4)
C31—P2—C21	98.52 (18)	C43—C42—H42	119.7
C11—P2—Ru1	116.26 (13)	C41—C42—H42	119.7
C31—P2—Ru1	119.75 (13)	C42—C43—C44	120.1 (4)
C21—P2—Ru1	113.37 (13)	C42—C43—H43	120.0
C61—P3—C51	104.19 (19)	C44—C43—H43	120.0
C61—P3—C41	98.26 (18)	C45—C44—C43	119.7 (4)
C51—P3—C41	102.50 (18)	C45—C44—H44	120.1
C61—P3—Ru1	121.33 (14)	C43—C44—H44	120.1
C51—P3—Ru1	113.93 (14)	C44—C45—C46	120.2 (5)
C41—P3—Ru1	114.01 (13)	C44—C45—H45	119.9
C2—C1—C5	107.2 (4)	C46—C45—H45	119.9
C2—C1—P1	129.1 (3)	C41—C46—C45	120.6 (4)
C5—C1—P1	123.5 (3)	C41—C46—H46	119.7
C2—C1—Fe1	69.4 (3)	C45—C46—H46	119.7
C5—C1—Fe1	69.3 (2)	C56—C51—C52	118.5 (4)
P1—C1—Fe1	123.3 (2)	C56—C51—P3	123.2 (3)
C1—C2—C3	107.9 (4)	C52—C51—P3	118.3 (3)
C1—C2—Fe1	69.8 (3)	C53—C52—C51	120.7 (4)
C3—C2—Fe1	69.8 (3)	C53—C52—H52	119.7
C1—C2—H2	126.0	C51—C52—H52	119.7
C3—C2—H2	126.0	C54—C53—C52	120.4 (5)
Fe1—C2—H2	125.9	C54—C53—H53	119.8
C4—C3—C2	108.7 (4)	C52—C53—H53	119.8
C4—C3—Fe1	69.9 (3)	C53—C54—C55	120.2 (4)
C2—C3—Fe1	69.3 (3)	C53—C54—H54	119.9
C4—C3—H3	125.6	C55—C54—H54	119.9
C2—C3—H3	125.6	C54—C55—C56	119.9 (5)
Fe1—C3—H3	126.8	C54—C55—H55	120.1
C5—C4—C3	107.8 (4)	C56—C55—H55	120.1
C5—C4—Fe1	69.5 (3)	C51—C56—C55	120.3 (5)
C3—C4—Fe1	69.6 (3)	C51—C56—H56	119.8
C5—C4—H4	126.1	C55—C56—H56	119.8
C3—C4—H4	126.1	C62—C61—C66	118.8 (4)
Fe1—C4—H4	126.4	C62—C61—P3	120.2 (3)
C4—C5—C1	108.4 (4)	C66—C61—P3	120.9 (3)
C4—C5—Fe1	70.0 (3)	C61—C62—C63	120.0 (4)
C1—C5—Fe1	69.3 (2)	C61—C62—H62	120.0
C4—C5—H5	125.8	C63—C62—H62	120.0
C1—C5—H5	125.8	C64—C63—C62	120.5 (5)
Fe1—C5—H5	126.5	C64—C63—H63	119.8
C7—C6—C10	107.9 (9)	C62—C63—H63	119.8
C7—C6—Fe1	70.3 (5)	C63—C64—C65	120.3 (5)
C10—C6—Fe1	70.9 (5)	C63—C64—H64	119.8
C7—C6—H6	126.0	C65—C64—H64	119.8
C10—C6—H6	126.0	C64—C65—C66	120.0 (5)
Fe1—C6—H6	124.4	C64—C65—H65	120.0
C6—C7—C8	111.4 (8)	C66—C65—H65	120.0
C6—C7—Fe1	70.9 (4)	C65—C66—C61	120.3 (5)
C8—C7—Fe1	70.8 (4)	C65—C66—H66	119.8
C6—C7—H7	124.3	C61—C66—H66	119.8
C8—C7—H7	124.3	Cl1S—C1S—Cl2S	119.8 (8)
Fe1—C7—H7	125.5	Cl1S—C1S—H1S1	107.4
C7—C8—C9	108.1 (8)	Cl2S—C1S—H1S1	107.4
C7—C8—Fe1	69.9 (4)	Cl1S—C1S—H1S2	107.4
C9—C8—Fe1	70.0 (4)	Cl2S—C1S—H1S2	107.4
C7—C8—H8	125.9	H1S1—C1S—H1S2	106.9

D—H···A	D—H	H···A	D···A	D—H···A
O3—H1S···O1i	0.82 (1)	1.72 (2)	2.515 (4)	162 (4)
O3—H2S···O3i	0.82 (1)	2.52 (6)	2.980 (6)	117 (5)

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O3—H1S⋯O1i	0.82 (1)	1.72 (2)	2.515 (4)	162 (4)
O3—H2S⋯O3i	0.82 (1)	2.52 (6)	2.980 (6)	117 (5)

Symmetry code: (i) .