Carbonyl-chlorido(1-methyl-sulfanylpenta-1,3-dien-1-yl-5-yl-idene)bis-(triphenyl-phosphane)osmium(II).

The crystal structure of the title compound, [Os(C(6)H(7)S)Cl(C(18)H(15)P)(2)(CO)], confirms the formulation as an osmabenzene. There is a slightly distorted octa-hedral coordination environment at the Os(II) ion, with the triphenyl-phosphane ligands mutually trans and the chloride cis to the carbon bearing the -SMe substituent. Within the metallacyclic ring, the C-C distances are appropriate for aromatic bonds and the two Os-C distances are shorter than typical Os-C single bonds. The maximum deviation from the least-squares plane through the osmabenzene ring occurs for the carbon bearing the SMe substituent [0.1037 (18) Å].

Related literature

For the synthesis and properties of metallabenzenes, see: Bleeke (2001 ▶); Landorf & Haley (2006 ▶); Wright (2006 ▶). For the synthesis and properties of osmabenzenes, see: Elliott et al. (1982 ▶, 1989 ▶); Rickard et al. (2000 ▶, 2001 ▶). For a discussion of ring planarity in metallabenzenes, see: Zhu et al. (2007 ▶). For spectroscopic data, see: Maddock et al. (1996 ▶).

Experimental

Crystal data

[Os(C6H7S)Cl(C18H15P)2(CO)]

M = 889.38

Monoclinic,

a = 13.5565 (1) Å

b = 15.7136 (2) Å

c = 18.2264 (3) Å

β = 109.978 (1)°

V = 3648.97 (8) Å3

Z = 4

Mo Kα radiation

μ = 3.75 mm−1

T = 203 K

0.33 × 0.28 × 0.11 mm

Data collection

Siemens SMART CCD area-detector diffractometer

Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ▶) T min = 0.491, T max = 0.739

22209 measured reflections

7812 independent reflections

6032 reflections with I > 2σ(I)

R int = 0.023

Refinement

R[F 2 > 2σ(F 2)] = 0.022

wR(F 2) = 0.060

S = 1.01

7812 reflections

444 parameters

H-atom parameters constrained

Δρmax = 1.01 e Å−3

Δρmin = −0.53 e Å−3

Data collection: SMART (Siemens, 1995 ▶); cell refinement: SAINT (Siemens, 1995 ▶); data reduction: SAINT; 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 ▶).

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536809039695/lh2916sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809039695/lh2916Isup2.hkl

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

[Os(C6H7S)Cl(C18H15P)2(CO)]	F(000) = 1768
Mr = 889.38	Dx = 1.619 Mg m−3
Monoclinic, P21/n	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2yn	Cell parameters from 8192 reflections
a = 13.5565 (1) Å	θ = 1.6–28.3°
b = 15.7136 (2) Å	µ = 3.75 mm−1
c = 18.2264 (3) Å	T = 203 K
β = 109.978 (1)°	Plates, blue
V = 3648.97 (8) Å3	0.33 × 0.28 × 0.11 mm
Z = 4

Siemens SMART CCD area-detector diffractometer	7812 independent reflections
Radiation source: fine-focus sealed tube	6032 reflections with I > 2σ(I)
graphite	Rint = 0.023
ω scans	θmax = 27.0°, θmin = 1.6°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −17→16
Tmin = 0.491, Tmax = 0.739	k = 0→19
22209 measured reflections	l = 0→23

Refinement on F2	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.022	H-atom parameters constrained
wR(F2) = 0.060	w = 1/[σ2(Fo2) + (0.0268P)2 + 2.9139P] where P = (Fo2 + 2Fc2)/3
S = 1.01	(Δ/σ)max = 0.004
7812 reflections	Δρmax = 1.01 e Å−3
444 parameters	Δρmin = −0.53 e Å−3
0 restraints	Extinction correction: SHELXL97 (Sheldrick, 2008), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.00065 (5)

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 > 2σ(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
Os1	0.503721 (7)	0.750195 (6)	0.123794 (5)	0.01728 (5)
Cl1	0.52137 (6)	0.89985 (5)	0.17787 (4)	0.03293 (16)
P1	0.35379 (5)	0.75535 (4)	0.16571 (4)	0.02055 (14)
P2	0.65608 (5)	0.75710 (4)	0.08534 (4)	0.02050 (14)
S1	0.41485 (6)	0.90387 (5)	0.00041 (4)	0.02726 (15)
O1	0.6180 (2)	0.6574 (2)	0.26956 (18)	0.0572 (7)
C1	0.4083 (2)	0.79638 (18)	0.01381 (16)	0.0235 (6)
C2	0.3413 (2)	0.74700 (19)	−0.04778 (18)	0.0314 (7)
H2A	0.2937	0.7754	−0.0907	0.038*
C3	0.3422 (2)	0.6598 (2)	−0.04821 (18)	0.0351 (7)
H3A	0.2913	0.6336	−0.0909	0.042*
C4	0.4089 (3)	0.6051 (2)	0.00668 (19)	0.0353 (7)
H4A	0.4057	0.5466	−0.0047	0.042*
C5	0.4789 (2)	0.63212 (18)	0.07632 (18)	0.0280 (6)
H5A	0.5222	0.5893	0.1069	0.034*
C6	0.5838 (2)	0.6926 (2)	0.2226 (2)	0.0331 (7)
C7	0.3395 (3)	0.9277 (2)	−0.10003 (18)	0.0413 (8)
H7A	0.3550	0.9851	−0.1122	0.062*
H7B	0.2652	0.9229	−0.1079	0.062*
H7C	0.3577	0.8878	−0.1340	0.062*
C11	0.3842 (2)	0.76453 (17)	0.27235 (16)	0.0235 (6)
C12	0.3095 (3)	0.7412 (2)	0.30511 (19)	0.0353 (7)
H12A	0.2436	0.7214	0.2727	0.042*
C13	0.3310 (3)	0.7467 (2)	0.3850 (2)	0.0426 (9)
H13A	0.2797	0.7303	0.4063	0.051*
C14	0.4268 (3)	0.7760 (2)	0.43332 (18)	0.0374 (8)
H14A	0.4411	0.7795	0.4875	0.045*
C15	0.5017 (2)	0.8001 (2)	0.40201 (17)	0.0326 (7)
H15A	0.5673	0.8203	0.4347	0.039*
C16	0.4802 (2)	0.79462 (19)	0.32186 (16)	0.0278 (6)
H16A	0.5316	0.8115	0.3008	0.033*
C21	0.2689 (2)	0.6613 (2)	0.14554 (17)	0.0290 (7)
C22	0.3159 (3)	0.5816 (2)	0.16040 (18)	0.0359 (7)
H22A	0.3894	0.5775	0.1759	0.043*
C23	0.2570 (3)	0.5082 (2)	0.1529 (2)	0.0493 (10)
H23A	0.2900	0.4547	0.1634	0.059*
C24	0.1479 (3)	0.5146 (3)	0.1294 (2)	0.0570 (12)
H24A	0.1070	0.4652	0.1243	0.068*
C25	0.1005 (3)	0.5922 (3)	0.1140 (2)	0.0549 (11)
H25A	0.0270	0.5958	0.0976	0.066*
C26	0.1597 (3)	0.6659 (2)	0.12214 (19)	0.0406 (8)
H26A	0.1262	0.7192	0.1119	0.049*
C31	0.2631 (2)	0.8443 (2)	0.12691 (16)	0.0253 (6)
C32	0.2611 (2)	0.9141 (2)	0.17292 (19)	0.0314 (7)
H32A	0.3027	0.9141	0.2261	0.038*
C33	0.1988 (3)	0.9836 (2)	0.1415 (2)	0.0401 (8)
H33A	0.1983	1.0304	0.1734	0.048*
C34	0.1374 (2)	0.9848 (2)	0.0637 (2)	0.0428 (9)
H34A	0.0958	1.0326	0.0424	0.051*
C35	0.1373 (2)	0.9154 (2)	0.0172 (2)	0.0409 (8)
H35A	0.0947	0.9157	−0.0357	0.049*
C36	0.1997 (2)	0.8454 (2)	0.04829 (18)	0.0335 (7)
H36A	0.1994	0.7984	0.0163	0.040*
C41	0.6232 (2)	0.78681 (19)	−0.01726 (16)	0.0249 (6)
C42	0.5683 (2)	0.7288 (2)	−0.07572 (18)	0.0325 (7)
H42A	0.5528	0.6740	−0.0622	0.039*
C43	0.5370 (3)	0.7532 (2)	−0.1540 (2)	0.0442 (9)
H43A	0.5027	0.7138	−0.1932	0.053*
C44	0.5558 (3)	0.8340 (3)	−0.1742 (2)	0.0459 (9)
H44A	0.5347	0.8497	−0.2271	0.055*
C45	0.6055 (3)	0.8925 (2)	−0.1170 (2)	0.0426 (9)
H45A	0.6161	0.9485	−0.1309	0.051*
C46	0.6399 (2)	0.8687 (2)	−0.03906 (19)	0.0321 (7)
H46A	0.6749	0.9085	−0.0005	0.038*
C51	0.7660 (2)	0.82842 (19)	0.13641 (17)	0.0265 (6)
C52	0.7716 (2)	0.8719 (2)	0.2035 (2)	0.0363 (8)
H52A	0.7183	0.8653	0.2252	0.044*
C53	0.8567 (3)	0.9258 (2)	0.2393 (2)	0.0502 (10)
H53A	0.8599	0.9559	0.2846	0.060*
C54	0.9353 (3)	0.9348 (2)	0.2086 (2)	0.0512 (10)
H54A	0.9913	0.9723	0.2321	0.061*
C55	0.9324 (3)	0.8887 (3)	0.1431 (2)	0.0523 (10)
H55A	0.9878	0.8931	0.1233	0.063*
C56	0.8481 (3)	0.8365 (2)	0.1071 (2)	0.0413 (8)
H56A	0.8458	0.8060	0.0623	0.050*
C61	0.7313 (2)	0.65751 (18)	0.09802 (17)	0.0233 (6)
C62	0.7491 (2)	0.6108 (2)	0.03920 (18)	0.0320 (7)
H62A	0.7202	0.6292	−0.0129	0.038*
C63	0.8093 (3)	0.5370 (2)	0.0568 (2)	0.0389 (8)
H63A	0.8204	0.5057	0.0164	0.047*
C64	0.8526 (2)	0.5094 (2)	0.13256 (19)	0.0334 (7)
H64A	0.8927	0.4592	0.1440	0.040*
C65	0.8371 (3)	0.5558 (2)	0.19159 (19)	0.0364 (7)
H65A	0.8668	0.5375	0.2436	0.044*
C66	0.7779 (2)	0.6290 (2)	0.17438 (18)	0.0353 (7)
H66A	0.7688	0.6606	0.2153	0.042*

	U11	U22	U33	U12	U13	U23
Os1	0.01787 (6)	0.01638 (6)	0.01841 (6)	−0.00104 (4)	0.00725 (4)	0.00086 (4)
Cl1	0.0314 (4)	0.0327 (4)	0.0342 (4)	−0.0012 (3)	0.0105 (3)	0.0008 (3)
P1	0.0185 (3)	0.0244 (4)	0.0191 (3)	−0.0022 (3)	0.0069 (3)	0.0012 (3)
P2	0.0199 (3)	0.0218 (4)	0.0214 (3)	−0.0007 (3)	0.0091 (3)	0.0001 (3)
S1	0.0287 (4)	0.0259 (4)	0.0262 (4)	0.0020 (3)	0.0081 (3)	0.0052 (3)
O1	0.0490 (16)	0.068 (2)	0.0625 (19)	0.0120 (15)	0.0288 (15)	0.0092 (16)
C1	0.0216 (13)	0.0274 (15)	0.0245 (14)	−0.0001 (11)	0.0117 (11)	0.0008 (12)
C2	0.0269 (14)	0.0362 (17)	0.0276 (15)	−0.0031 (13)	0.0048 (12)	−0.0002 (13)
C3	0.0302 (16)	0.0405 (19)	0.0320 (17)	−0.0140 (14)	0.0072 (13)	−0.0079 (14)
C4	0.0419 (18)	0.0235 (15)	0.0453 (19)	−0.0079 (14)	0.0210 (15)	−0.0047 (14)
C5	0.0300 (15)	0.0228 (14)	0.0366 (17)	−0.0020 (12)	0.0187 (13)	−0.0002 (12)
C6	0.0261 (16)	0.0375 (19)	0.0424 (19)	−0.0048 (14)	0.0207 (15)	−0.0094 (15)
C7	0.049 (2)	0.044 (2)	0.0268 (16)	0.0060 (16)	0.0071 (15)	0.0135 (14)
C11	0.0260 (14)	0.0235 (14)	0.0205 (13)	−0.0003 (11)	0.0073 (11)	0.0017 (11)
C12	0.0294 (15)	0.051 (2)	0.0290 (16)	−0.0121 (14)	0.0145 (13)	−0.0062 (14)
C13	0.0410 (18)	0.064 (3)	0.0313 (17)	−0.0146 (17)	0.0228 (15)	−0.0024 (16)
C14	0.0458 (19)	0.0481 (19)	0.0208 (15)	−0.0048 (16)	0.0143 (14)	−0.0001 (14)
C15	0.0336 (17)	0.0376 (18)	0.0224 (15)	−0.0039 (13)	0.0041 (13)	0.0000 (13)
C16	0.0281 (15)	0.0322 (16)	0.0240 (14)	−0.0053 (13)	0.0101 (12)	0.0019 (12)
C21	0.0314 (15)	0.0355 (17)	0.0206 (14)	−0.0126 (13)	0.0096 (12)	−0.0002 (12)
C22	0.0433 (19)	0.0350 (18)	0.0321 (17)	−0.0121 (15)	0.0166 (15)	0.0006 (14)
C23	0.079 (3)	0.0332 (19)	0.040 (2)	−0.0201 (19)	0.0262 (19)	0.0002 (16)
C24	0.070 (3)	0.061 (3)	0.037 (2)	−0.043 (2)	0.0148 (19)	−0.0004 (19)
C25	0.0381 (19)	0.078 (3)	0.043 (2)	−0.030 (2)	0.0065 (16)	0.006 (2)
C26	0.0288 (16)	0.052 (2)	0.0386 (19)	−0.0146 (15)	0.0088 (14)	0.0055 (16)
C31	0.0167 (12)	0.0344 (17)	0.0274 (15)	0.0017 (12)	0.0107 (11)	0.0069 (12)
C32	0.0275 (15)	0.0335 (17)	0.0340 (16)	0.0028 (13)	0.0116 (13)	0.0033 (14)
C33	0.0327 (17)	0.0363 (19)	0.054 (2)	0.0054 (14)	0.0179 (16)	0.0041 (16)
C34	0.0255 (16)	0.043 (2)	0.062 (2)	0.0101 (14)	0.0178 (16)	0.0202 (18)
C35	0.0217 (15)	0.064 (2)	0.0350 (18)	0.0087 (15)	0.0067 (13)	0.0186 (17)
C36	0.0256 (15)	0.0463 (19)	0.0299 (16)	0.0022 (14)	0.0110 (13)	0.0041 (14)
C41	0.0243 (14)	0.0291 (15)	0.0246 (14)	0.0035 (12)	0.0127 (12)	0.0050 (12)
C42	0.0258 (15)	0.0433 (18)	0.0278 (16)	−0.0019 (13)	0.0084 (13)	0.0027 (13)
C43	0.0329 (17)	0.071 (3)	0.0270 (16)	−0.0006 (17)	0.0081 (14)	−0.0040 (17)
C44	0.0354 (18)	0.073 (3)	0.0328 (18)	0.0145 (18)	0.0162 (15)	0.0186 (18)
C45	0.0390 (18)	0.048 (2)	0.049 (2)	0.0121 (16)	0.0245 (17)	0.0231 (17)
C46	0.0315 (16)	0.0301 (16)	0.0377 (17)	0.0078 (13)	0.0158 (14)	0.0064 (13)
C51	0.0216 (13)	0.0247 (15)	0.0318 (16)	−0.0023 (11)	0.0072 (12)	0.0013 (12)
C52	0.0231 (15)	0.0390 (19)	0.0425 (19)	0.0009 (13)	0.0057 (14)	−0.0112 (15)
C53	0.0356 (18)	0.045 (2)	0.058 (2)	0.0001 (16)	0.0003 (17)	−0.0200 (18)
C54	0.0326 (18)	0.037 (2)	0.072 (3)	−0.0124 (15)	0.0012 (18)	−0.0025 (19)
C55	0.0328 (18)	0.066 (3)	0.059 (2)	−0.0197 (18)	0.0167 (18)	0.008 (2)
C56	0.0372 (18)	0.051 (2)	0.0406 (19)	−0.0133 (16)	0.0191 (16)	−0.0053 (16)
C61	0.0217 (13)	0.0223 (14)	0.0284 (15)	0.0008 (11)	0.0117 (11)	0.0008 (12)
C62	0.0350 (16)	0.0359 (17)	0.0262 (15)	0.0035 (14)	0.0117 (13)	0.0004 (13)
C63	0.0455 (19)	0.0341 (18)	0.0397 (18)	0.0071 (15)	0.0177 (16)	−0.0108 (14)
C64	0.0316 (16)	0.0246 (15)	0.0435 (19)	0.0037 (13)	0.0120 (14)	0.0012 (14)
C65	0.0362 (17)	0.0371 (18)	0.0347 (17)	0.0111 (14)	0.0106 (14)	0.0067 (14)
C66	0.0381 (18)	0.0425 (19)	0.0258 (16)	0.0130 (14)	0.0118 (14)	0.0029 (14)

Os1—C6	1.976 (4)	C25—H25A	0.9400
Os1—C1	2.109 (3)	C26—H26A	0.9400
Os1—C5	2.026 (3)	C31—C32	1.387 (4)
Os1—P2	2.3996 (7)	C31—C36	1.397 (4)
Os1—P1	2.4047 (7)	C32—C33	1.379 (4)
Os1—Cl1	2.5293 (8)	C32—H32A	0.9400
P1—C21	1.832 (3)	C33—C34	1.378 (5)
P1—C31	1.836 (3)	C33—H33A	0.9400
P1—C11	1.850 (3)	C34—C35	1.380 (5)
P2—C41	1.829 (3)	C34—H34A	0.9400
P2—C61	1.839 (3)	C35—C36	1.385 (4)
P2—C51	1.843 (3)	C35—H35A	0.9400
S1—C1	1.713 (3)	C36—H36A	0.9400
S1—C7	1.805 (3)	C41—C46	1.388 (4)
O1—C6	0.992 (4)	C41—C42	1.406 (4)
C1—C2	1.410 (4)	C42—C43	1.396 (5)
C2—C3	1.370 (4)	C42—H42A	0.9400
C2—H2A	0.9400	C43—C44	1.371 (5)
C3—C4	1.393 (5)	C43—H43A	0.9400
C3—H3A	0.9400	C44—C45	1.380 (5)
C4—C5	1.367 (4)	C44—H44A	0.9400
C4—H4A	0.9400	C45—C46	1.388 (4)
C5—H5A	0.9400	C45—H45A	0.9400
C7—H7A	0.9700	C46—H46A	0.9400
C7—H7B	0.9700	C51—C52	1.380 (4)
C7—H7C	0.9700	C51—C56	1.394 (4)
C11—C12	1.389 (4)	C52—C53	1.400 (4)
C11—C16	1.389 (4)	C52—H52A	0.9400
C12—C13	1.387 (4)	C53—C54	1.370 (6)
C12—H12A	0.9400	C53—H53A	0.9400
C13—C14	1.376 (5)	C54—C55	1.386 (6)
C13—H13A	0.9400	C54—H54A	0.9400
C14—C15	1.378 (4)	C55—C56	1.378 (5)
C14—H14A	0.9400	C55—H55A	0.9400
C15—C16	1.391 (4)	C56—H56A	0.9400
C15—H15A	0.9400	C61—C62	1.386 (4)
C16—H16A	0.9400	C61—C66	1.391 (4)
C21—C22	1.389 (5)	C62—C63	1.392 (4)
C21—C26	1.395 (4)	C62—H62A	0.9400
C22—C23	1.383 (4)	C63—C64	1.373 (5)
C22—H22A	0.9400	C63—H63A	0.9400
C23—C24	1.395 (6)	C64—C65	1.374 (4)
C23—H23A	0.9400	C64—H64A	0.9400
C24—C25	1.362 (6)	C65—C66	1.376 (4)
C24—H24A	0.9400	C65—H65A	0.9400
C25—C26	1.388 (5)	C66—H66A	0.9400
C6—Os1—C5	85.91 (13)	C23—C24—H24A	119.9
C6—Os1—C1	172.52 (12)	C24—C25—C26	120.7 (4)
C5—Os1—C1	87.18 (12)	C24—C25—H25A	119.7
C6—Os1—P2	91.54 (9)	C26—C25—H25A	119.7
C5—Os1—P2	87.16 (8)	C25—C26—C21	120.2 (4)
C1—Os1—P2	90.95 (7)	C25—C26—H26A	119.9
C6—Os1—P1	89.25 (9)	C21—C26—H26A	119.9
C5—Os1—P1	97.56 (8)	C32—C31—C36	118.5 (3)
C1—Os1—P1	88.84 (7)	C32—C31—P1	121.2 (2)
P2—Os1—P1	175.26 (2)	C36—C31—P1	120.1 (2)
C6—Os1—Cl1	97.00 (10)	C33—C32—C31	120.7 (3)
C5—Os1—Cl1	176.00 (9)	C33—C32—H32A	119.6
C1—Os1—Cl1	89.78 (8)	C31—C32—H32A	119.6
P2—Os1—Cl1	95.48 (2)	C34—C33—C32	120.5 (3)
P1—Os1—Cl1	79.78 (2)	C34—C33—H33A	119.7
C21—P1—C31	104.19 (15)	C32—C33—H33A	119.7
C21—P1—C11	99.96 (13)	C33—C34—C35	119.6 (3)
C31—P1—C11	103.00 (13)	C33—C34—H34A	120.2
C21—P1—Os1	116.76 (10)	C35—C34—H34A	120.2
C31—P1—Os1	115.50 (9)	C34—C35—C36	120.3 (3)
C11—P1—Os1	115.31 (10)	C34—C35—H35A	119.8
C41—P2—C61	106.08 (13)	C36—C35—H35A	119.8
C41—P2—C51	103.53 (14)	C35—C36—C31	120.3 (3)
C61—P2—C51	97.81 (13)	C35—C36—H36A	119.8
C41—P2—Os1	112.12 (9)	C31—C36—H36A	119.8
C61—P2—Os1	114.88 (9)	C46—C41—C42	118.7 (3)
C51—P2—Os1	120.54 (10)	C46—C41—P2	121.5 (2)
C1—S1—C7	108.06 (15)	C42—C41—P2	119.4 (2)
C2—C1—S1	118.7 (2)	C43—C42—C41	119.6 (3)
C2—C1—Os1	125.9 (2)	C43—C42—H42A	120.2
S1—C1—Os1	115.46 (15)	C41—C42—H42A	120.2
C3—C2—C1	123.4 (3)	C44—C43—C42	120.6 (3)
C3—C2—H2A	118.3	C44—C43—H43A	119.7
C1—C2—H2A	118.3	C42—C43—H43A	119.7
C2—C3—C4	128.2 (3)	C43—C44—C45	120.1 (3)
C2—C3—H3A	115.9	C43—C44—H44A	119.9
C4—C3—H3A	115.9	C45—C44—H44A	119.9
C5—C4—C3	123.3 (3)	C44—C45—C46	120.0 (3)
C5—C4—H4A	118.3	C44—C45—H45A	120.0
C3—C4—H4A	118.3	C46—C45—H45A	120.0
C4—C5—Os1	130.0 (2)	C45—C46—C41	120.9 (3)
C4—C5—H5A	115.0	C45—C46—H46A	119.6
Os1—C5—H5A	115.0	C41—C46—H46A	119.6
O1—C6—Os1	172.7 (4)	C52—C51—C56	119.0 (3)
S1—C7—H7A	109.5	C52—C51—P2	122.6 (2)
S1—C7—H7B	109.5	C56—C51—P2	118.4 (2)
H7A—C7—H7B	109.5	C51—C52—C53	119.9 (3)
S1—C7—H7C	109.5	C51—C52—H52A	120.0
H7A—C7—H7C	109.5	C53—C52—H52A	120.0
H7B—C7—H7C	109.5	C54—C53—C52	120.4 (4)
C12—C11—C16	118.0 (3)	C54—C53—H53A	119.8
C12—C11—P1	119.8 (2)	C52—C53—H53A	119.8
C16—C11—P1	122.1 (2)	C53—C54—C55	120.0 (3)
C13—C12—C11	120.8 (3)	C53—C54—H54A	120.0
C13—C12—H12A	119.6	C55—C54—H54A	120.0
C11—C12—H12A	119.6	C56—C55—C54	119.7 (3)
C14—C13—C12	120.4 (3)	C56—C55—H55A	120.1
C14—C13—H13A	119.8	C54—C55—H55A	120.1
C12—C13—H13A	119.8	C55—C56—C51	120.9 (3)
C13—C14—C15	119.7 (3)	C55—C56—H56A	119.5
C13—C14—H14A	120.1	C51—C56—H56A	119.5
C15—C14—H14A	120.1	C62—C61—C66	117.6 (3)
C14—C15—C16	119.9 (3)	C62—C61—P2	126.0 (2)
C14—C15—H15A	120.1	C66—C61—P2	116.3 (2)
C16—C15—H15A	120.1	C61—C62—C63	120.4 (3)
C11—C16—C15	121.1 (3)	C61—C62—H62A	119.8
C11—C16—H16A	119.4	C63—C62—H62A	119.8
C15—C16—H16A	119.4	C64—C63—C62	120.7 (3)
C22—C21—C26	118.4 (3)	C64—C63—H63A	119.6
C22—C21—P1	118.3 (2)	C62—C63—H63A	119.6
C26—C21—P1	123.2 (3)	C63—C64—C65	119.5 (3)
C23—C22—C21	121.5 (3)	C63—C64—H64A	120.2
C23—C22—H22A	119.3	C65—C64—H64A	120.2
C21—C22—H22A	119.3	C64—C65—C66	119.9 (3)
C22—C23—C24	119.1 (4)	C64—C65—H65A	120.1
C22—C23—H23A	120.5	C66—C65—H65A	120.1
C24—C23—H23A	120.5	C65—C66—C61	121.8 (3)
C25—C24—C23	120.2 (3)	C65—C66—H66A	119.1
C25—C24—H24A	119.9	C61—C66—H66A	119.1

Table 1

Selected bond lengths (Å)

Os1—C1	2.109 (3)
Os1—C5	2.026 (3)
C1—C2	1.410 (4)
C2—C3	1.370 (4)
C3—C4	1.393 (5)
C4—C5	1.367 (4)