(η(6)-Benzene)-dichlorido(dicyclo-hexyl-phenyl-phosphane)ruthenium(II) benzene sesquisolvate.

The asymmetric unit of the title compound, [RuCl2(C6H6)(C18H27P)]·1.5C6H6, contains one mol-ecule of the Ru(II) complex and one and a half solvent molecules as one of these is located about a centre of inversion. The Ru(II) atom has a classical three-legged piano-stool environment being coordinated by an η(6)-benzene ligand [Ru-centroid = 1.6964 (6) Å], two chloride ligands with an average Ru-Cl bond length of 2.4138 (3) Å and a dicyclo-hexyl-phenyl-phosphane ligand [Ru-P = 2.3786 (3) Å]. The effective cone angle for the phosphane was calculated to be 158°. In the crystal, weak C-H⋯Cl hydrogen bonds link the Ru(II) complexes into centrosymmetric dimers. The crystal packing exhibits intra- and inter-molecular C-H⋯π inter-actions resulting in a zigzag pattern in the [101] direction.

Related literature

For background to the catalytic activity of RuII–arene complexes, see: Chen et al. (2002 ▶); Crochet et al. (2003 ▶); Aydemir et al. (2011 ▶); Wang et al. (2011 ▶). For ring-opening metathesis polymerization with Ru–arene complexes, see: Stumpf et al. (1995 ▶). For background to cone angles, see: Tolman (1977 ▶); Otto (2001 ▶). For a description of the Cambridge Structural Database, see: Allen (2002 ▶).

Experimental

Crystal data

[RuCl2(C6H6)(C18H27P)]·1.5C6H6

M = 641.61

Triclinic,

a = 10.0893 (8) Å

b = 10.8325 (9) Å

c = 14.4937 (12) Å

α = 90.346 (2)°

β = 91.748 (1)°

γ = 106.979 (1)°

V = 1514.1 (2) Å3

Z = 2

Mo Kα radiation

μ = 0.77 mm−1

T = 100 K

0.43 × 0.17 × 0.16 mm

Data collection

Bruker APEX DUO 4K CCD diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2008 ▶) T min = 0.734, T max = 0.887

49345 measured reflections

7589 independent reflections

7093 reflections with I > 2σ(I)

R int = 0.022

Refinement

R[F 2 > 2σ(F 2)] = 0.018

wR(F 2) = 0.048

S = 1.03

7589 reflections

334 parameters

H-atom parameters constrained

Δρmax = 0.54 e Å−3

Δρmin = −0.43 e Å−3

Data collection: APEX2 (Bruker, 2011 ▶); cell refinement: SAINT (Bruker, 2008 ▶); data reduction: SAINT and XPREP (Bruker, 2008 ▶); program(s) used to solve structure: SIR97 (Altomare et al., 1999 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: DIAMOND (Brandenburg & Putz, 2005 ▶); software used to prepare material for publication: publCIF (Westrip, 2010 ▶) and WinGX (Farrugia, 1999 ▶).

Click here for additional data file.

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S1600536812044674/cv5349sup1.cif

Click here for additional data file.

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536812044674/cv5349Isup2.hkl

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

[RuCl2(C6H6)(C18H27P)]·1.5C6H6	Z = 2
Mr = 641.61	F(000) = 666
Triclinic, P1	Dx = 1.407 Mg m−3
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 10.0893 (8) Å	Cell parameters from 9969 reflections
b = 10.8325 (9) Å	θ = 2.4–28.4°
c = 14.4937 (12) Å	µ = 0.77 mm−1
α = 90.346 (2)°	T = 100 K
β = 91.748 (1)°	Needle, orange
γ = 106.979 (1)°	0.43 × 0.17 × 0.16 mm
V = 1514.1 (2) Å3

Bruker APEX DUO 4K CCD diffractometer	7589 independent reflections
Radiation source: sealed tube	7093 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.022
Detector resolution: 8.4 pixels mm-1	θmax = 28.4°, θmin = 2.0°
φ and ω scans	h = −12→13
Absorption correction: multi-scan (SADABS; Bruker, 2008)	k = −14→14
Tmin = 0.734, Tmax = 0.887	l = −19→19
49345 measured reflections

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)] = 0.018	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.048	H-atom parameters constrained
S = 1.03	w = 1/[σ2(Fo2) + (0.0236P)2 + 0.8124P] where P = (Fo2 + 2Fc2)/3
7589 reflections	(Δ/σ)max = 0.006
334 parameters	Δρmax = 0.54 e Å−3
0 restraints	Δρmin = −0.43 e Å−3

Experimental. The intensity data was collected on a Bruker Apex DUO 4 K CCD diffractometer using an exposure time of 10 s/frame. A total of 3975 frames were collected with a frame width of 0.5° covering up to θ = 28.39° with 99.8% completeness accomplished.

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
C13	0.23801 (12)	0.90129 (11)	0.13276 (8)	0.0128 (2)
H13	0.2204	0.8214	0.1704	0.015*
Ru1	0.291263 (9)	1.021309 (9)	0.364239 (6)	0.01185 (3)
Cl2	0.35692 (3)	0.82818 (3)	0.330250 (19)	0.01576 (6)
Cl1	0.51362 (3)	1.14613 (3)	0.310072 (19)	0.01539 (6)
P1	0.20357 (3)	1.02428 (3)	0.210321 (19)	0.01140 (6)
C21	−0.20563 (14)	1.02643 (15)	0.22475 (9)	0.0240 (3)
H21	−0.2563	1.0878	0.2254	0.029*
C24	−0.05677 (13)	0.84778 (13)	0.22298 (9)	0.0199 (2)
H24	−0.0066	0.786	0.2228	0.024*
C7	0.27287 (12)	1.18293 (11)	0.15452 (8)	0.0141 (2)
H7	0.3714	1.1894	0.1416	0.017*
C3	0.34809 (14)	1.10795 (13)	0.50804 (8)	0.0205 (2)
H3	0.4342	1.1512	0.5383	0.025*
C19	0.01393 (12)	0.97891 (12)	0.21045 (8)	0.0151 (2)
C12	0.28055 (14)	1.29985 (12)	0.21791 (8)	0.0189 (2)
H12A	0.1856	1.3019	0.2314	0.023*
H12B	0.3285	1.2914	0.2771	0.023*
C15	0.17462 (13)	0.74268 (12)	−0.00063 (8)	0.0184 (2)
H15A	0.1478	0.6683	0.0413	0.022*
H15B	0.1177	0.7191	−0.0585	0.022*
C6	0.08641 (13)	0.98146 (14)	0.42244 (8)	0.0207 (3)
H6	−0.0029	0.9389	0.3963	0.025*
C5	0.16284 (14)	0.91076 (14)	0.47028 (9)	0.0217 (3)
H5	0.1282	0.8193	0.472	0.026*
C9	0.28183 (16)	1.32479 (12)	0.01475 (9)	0.0227 (3)
H9A	0.3764	1.3232	−0.0004	0.027*
H9B	0.2323	1.334	−0.0436	0.027*
C23	−0.19916 (14)	0.80717 (14)	0.23563 (10)	0.0247 (3)
H23	−0.2455	0.7181	0.2432	0.03*
C2	0.27617 (14)	1.18010 (13)	0.45379 (8)	0.0197 (2)
H2	0.3173	1.2698	0.4449	0.024*
C1	0.14425 (13)	1.11748 (13)	0.41362 (8)	0.0199 (2)
H1	0.094	1.1659	0.3807	0.024*
C20	−0.06275 (13)	1.06759 (13)	0.21126 (8)	0.0188 (2)
H20	−0.0174	1.1566	0.2026	0.023*
C22	−0.27381 (14)	0.89684 (15)	0.23717 (9)	0.0255 (3)
H22	−0.3707	0.8694	0.2467	0.031*
C4	0.29264 (14)	0.97544 (14)	0.51658 (8)	0.0216 (3)
H4	0.3402	0.9279	0.5528	0.026*
C17	0.42054 (13)	0.81708 (12)	0.06445 (8)	0.0166 (2)
H17A	0.5191	0.8397	0.0478	0.02*
H17B	0.4037	0.7463	0.1095	0.02*
C8	0.20528 (14)	1.19726 (12)	0.05982 (8)	0.0187 (2)
H8A	0.2067	1.1243	0.0188	0.022*
H8B	0.1073	1.1941	0.0679	0.022*
C29	0.13687 (16)	0.64750 (15)	0.65832 (10)	0.0294 (3)
H29	0.2034	0.7136	0.6276	0.035*
C25	−0.08721 (15)	0.49053 (14)	0.65995 (11)	0.0298 (3)
H25	−0.174	0.4484	0.6301	0.036*
C10	0.29188 (18)	1.44049 (13)	0.07790 (10)	0.0281 (3)
H10A	0.1979	1.4486	0.0869	0.034*
H10B	0.3476	1.5203	0.0485	0.034*
C30	0.00960 (16)	0.58659 (15)	0.61498 (10)	0.0297 (3)
H30	−0.0109	0.6108	0.5546	0.036*
C11	0.35888 (16)	1.42569 (12)	0.17166 (10)	0.0257 (3)
H11A	0.3598	1.4998	0.2123	0.031*
H11B	0.4562	1.4266	0.1632	0.031*
C27	0.06923 (17)	0.51601 (14)	0.79164 (10)	0.0281 (3)
H27	0.0895	0.4918	0.8521	0.034*
C28	0.16672 (16)	0.61169 (14)	0.74646 (10)	0.0288 (3)
H28	0.2541	0.6528	0.7759	0.035*
C26	−0.05788 (16)	0.45575 (13)	0.74830 (11)	0.0284 (3)
H26	−0.125	0.3905	0.7793	0.034*
C18	0.39160 (12)	0.93493 (11)	0.10898 (8)	0.0143 (2)
H18A	0.4145	1.008	0.0658	0.017*
H18B	0.4504	0.9612	0.1658	0.017*
C14	0.14528 (13)	0.86015 (12)	0.04474 (8)	0.0176 (2)
H14A	0.0465	0.838	0.0607	0.021*
H14B	0.1641	0.9325	0.0009	0.021*
C16	0.32791 (13)	0.77092 (12)	−0.02223 (8)	0.0180 (2)
H16A	0.3521	0.8381	−0.0699	0.022*
H16B	0.3447	0.6918	−0.0472	0.022*
C31	0.52440 (16)	0.43687 (14)	0.57897 (10)	0.0283 (3)
H31	0.541	0.3936	0.633	0.034*
C32	0.59078 (16)	0.42566 (14)	0.49868 (11)	0.0293 (3)
H32	0.6532	0.3748	0.4977	0.035*
C33	0.43334 (16)	0.51160 (14)	0.58070 (11)	0.0291 (3)
H33	0.3878	0.5197	0.6358	0.035*

	U11	U22	U33	U12	U13	U23
C13	0.0132 (5)	0.0144 (5)	0.0112 (5)	0.0050 (4)	−0.0004 (4)	−0.0011 (4)
Ru1	0.01057 (5)	0.01581 (5)	0.00970 (5)	0.00475 (3)	−0.00032 (3)	0.00017 (3)
Cl2	0.01653 (13)	0.01590 (12)	0.01587 (12)	0.00649 (10)	−0.00139 (10)	0.00159 (10)
Cl1	0.01180 (12)	0.01761 (13)	0.01576 (12)	0.00284 (10)	−0.00064 (10)	0.00031 (10)
P1	0.01084 (13)	0.01358 (13)	0.01068 (13)	0.00509 (10)	−0.00095 (10)	−0.00060 (10)
C21	0.0192 (6)	0.0392 (8)	0.0191 (6)	0.0170 (6)	−0.0003 (5)	−0.0004 (5)
C24	0.0154 (6)	0.0228 (6)	0.0218 (6)	0.0060 (5)	0.0005 (5)	−0.0028 (5)
C7	0.0158 (5)	0.0138 (5)	0.0134 (5)	0.0055 (4)	−0.0009 (4)	0.0000 (4)
C3	0.0196 (6)	0.0323 (7)	0.0105 (5)	0.0097 (5)	−0.0018 (4)	−0.0046 (5)
C19	0.0121 (5)	0.0222 (6)	0.0121 (5)	0.0067 (4)	−0.0013 (4)	−0.0019 (4)
C12	0.0259 (6)	0.0163 (5)	0.0156 (5)	0.0085 (5)	−0.0024 (5)	−0.0023 (4)
C15	0.0220 (6)	0.0181 (6)	0.0152 (5)	0.0064 (5)	−0.0021 (5)	−0.0037 (4)
C6	0.0143 (6)	0.0338 (7)	0.0138 (5)	0.0065 (5)	0.0035 (4)	−0.0019 (5)
C5	0.0214 (6)	0.0282 (7)	0.0150 (6)	0.0057 (5)	0.0069 (5)	0.0040 (5)
C9	0.0350 (7)	0.0187 (6)	0.0165 (6)	0.0108 (5)	0.0019 (5)	0.0030 (5)
C23	0.0160 (6)	0.0296 (7)	0.0247 (7)	0.0008 (5)	0.0011 (5)	−0.0029 (5)
C2	0.0232 (6)	0.0252 (6)	0.0128 (5)	0.0103 (5)	0.0004 (5)	−0.0049 (5)
C1	0.0191 (6)	0.0322 (7)	0.0128 (5)	0.0144 (5)	0.0012 (4)	−0.0027 (5)
C20	0.0181 (6)	0.0260 (6)	0.0150 (5)	0.0107 (5)	0.0000 (4)	−0.0001 (5)
C22	0.0122 (6)	0.0445 (8)	0.0195 (6)	0.0080 (6)	0.0002 (5)	−0.0022 (6)
C4	0.0234 (6)	0.0347 (7)	0.0100 (5)	0.0133 (6)	0.0024 (5)	0.0042 (5)
C17	0.0179 (6)	0.0187 (5)	0.0155 (5)	0.0086 (5)	0.0023 (4)	−0.0001 (4)
C8	0.0247 (6)	0.0181 (6)	0.0138 (5)	0.0075 (5)	−0.0029 (5)	0.0006 (4)
C29	0.0274 (7)	0.0277 (7)	0.0265 (7)	−0.0026 (6)	0.0052 (6)	0.0001 (6)
C25	0.0208 (7)	0.0254 (7)	0.0402 (8)	0.0026 (5)	−0.0036 (6)	−0.0017 (6)
C10	0.0477 (9)	0.0177 (6)	0.0219 (6)	0.0143 (6)	0.0010 (6)	0.0028 (5)
C30	0.0328 (8)	0.0284 (7)	0.0251 (7)	0.0048 (6)	−0.0028 (6)	0.0004 (6)
C11	0.0376 (8)	0.0147 (6)	0.0238 (7)	0.0066 (5)	−0.0025 (6)	−0.0016 (5)
C27	0.0383 (8)	0.0232 (6)	0.0234 (7)	0.0100 (6)	0.0012 (6)	−0.0002 (5)
C28	0.0249 (7)	0.0286 (7)	0.0280 (7)	0.0011 (6)	−0.0031 (6)	−0.0057 (6)
C26	0.0276 (7)	0.0185 (6)	0.0376 (8)	0.0036 (5)	0.0098 (6)	0.0035 (5)
C18	0.0143 (5)	0.0154 (5)	0.0138 (5)	0.0050 (4)	0.0018 (4)	−0.0001 (4)
C14	0.0184 (6)	0.0212 (6)	0.0148 (5)	0.0089 (5)	−0.0043 (4)	−0.0049 (4)
C16	0.0237 (6)	0.0182 (6)	0.0141 (5)	0.0094 (5)	0.0016 (5)	−0.0017 (4)
C31	0.0353 (8)	0.0228 (6)	0.0273 (7)	0.0108 (6)	−0.0125 (6)	−0.0045 (5)
C32	0.0307 (7)	0.0253 (7)	0.0353 (8)	0.0147 (6)	−0.0106 (6)	−0.0079 (6)
C33	0.0328 (8)	0.0269 (7)	0.0283 (7)	0.0106 (6)	−0.0043 (6)	−0.0071 (6)

C13—C18	1.5352 (16)	C23—C22	1.393 (2)
C13—C14	1.5422 (15)	C23—H23	0.95
C13—P1	1.8536 (11)	C2—C1	1.4111 (18)
C13—H13	1	C2—H2	0.95
Ru1—C5	2.1708 (13)	C1—H1	0.95
Ru1—C1	2.1808 (12)	C20—H20	0.95
Ru1—C6	2.1816 (13)	C22—H22	0.95
Ru1—C2	2.1919 (12)	C4—H4	0.95
Ru1—C4	2.2667 (12)	C17—C16	1.5328 (17)
Ru1—C3	2.2677 (12)	C17—C18	1.5333 (16)
Ru1—P1	2.3786 (3)	C17—H17A	0.99
Ru1—Cl1	2.4137 (3)	C17—H17B	0.99
Ru1—Cl2	2.4239 (3)	C8—H8A	0.99
P1—C19	1.8312 (12)	C8—H8B	0.99
P1—C7	1.8564 (12)	C29—C28	1.387 (2)
C21—C22	1.387 (2)	C29—C30	1.389 (2)
C21—C20	1.3993 (18)	C29—H29	0.95
C21—H21	0.95	C25—C30	1.384 (2)
C24—C23	1.3925 (18)	C25—C26	1.385 (2)
C24—C19	1.4067 (18)	C25—H25	0.95
C24—H24	0.95	C10—C11	1.5295 (19)
C7—C12	1.5422 (16)	C10—H10A	0.99
C7—C8	1.5429 (16)	C10—H10B	0.99
C7—H7	1	C30—H30	0.95
C3—C4	1.388 (2)	C11—H11A	0.99
C3—C2	1.4351 (18)	C11—H11B	0.99
C3—H3	0.95	C27—C26	1.387 (2)
C19—C20	1.3986 (17)	C27—C28	1.387 (2)
C12—C11	1.5318 (18)	C27—H27	0.95
C12—H12A	0.99	C28—H28	0.95
C12—H12B	0.99	C26—H26	0.95
C15—C16	1.5290 (18)	C18—H18A	0.99
C15—C14	1.5366 (16)	C18—H18B	0.99
C15—H15A	0.99	C14—H14A	0.99
C15—H15B	0.99	C14—H14B	0.99
C6—C5	1.4074 (19)	C16—H16A	0.99
C6—C1	1.426 (2)	C16—H16B	0.99
C6—H6	0.95	C31—C32	1.382 (2)
C5—C4	1.4357 (19)	C31—C33	1.391 (2)
C5—H5	0.95	C31—H31	0.95
C9—C10	1.5249 (18)	C32—C33i	1.391 (2)
C9—C8	1.5330 (18)	C32—H32	0.95
C9—H9A	0.99	C33—C32i	1.391 (2)
C9—H9B	0.99	C33—H33	0.95
C18—C13—C14	110.24 (9)	H9A—C9—H9B	107.9
C18—C13—P1	111.93 (8)	C24—C23—C22	120.14 (13)
C14—C13—P1	118.23 (8)	C24—C23—H23	119.9
C18—C13—H13	105.1	C22—C23—H23	119.9
C14—C13—H13	105.1	C1—C2—C3	119.86 (12)
P1—C13—H13	105.1	C1—C2—Ru1	70.74 (7)
C5—Ru1—C1	68.40 (5)	C3—C2—Ru1	74.12 (7)
C5—Ru1—C6	37.73 (5)	C1—C2—H2	120.1
C1—Ru1—C6	38.15 (5)	C3—C2—H2	120.1
C5—Ru1—C2	80.54 (5)	Ru1—C2—H2	127
C1—Ru1—C2	37.65 (5)	C2—C1—C6	119.93 (12)
C6—Ru1—C2	68.32 (5)	C2—C1—Ru1	71.60 (7)
C5—Ru1—C4	37.68 (5)	C6—C1—Ru1	70.96 (7)
C1—Ru1—C4	79.39 (5)	C2—C1—H1	120
C6—Ru1—C4	67.44 (5)	C6—C1—H1	120
C2—Ru1—C4	66.63 (5)	Ru1—C1—H1	129.9
C5—Ru1—C3	66.62 (5)	C19—C20—C21	120.63 (13)
C1—Ru1—C3	67.21 (5)	C19—C20—H20	119.7
C6—Ru1—C3	79.24 (5)	C21—C20—H20	119.7
C2—Ru1—C3	37.50 (5)	C21—C22—C23	119.51 (12)
C4—Ru1—C3	35.64 (5)	C21—C22—H22	120.2
C5—Ru1—P1	121.28 (4)	C23—C22—H22	120.2
C1—Ru1—P1	90.39 (3)	C3—C4—C5	119.47 (12)
C6—Ru1—P1	93.12 (3)	C3—C4—Ru1	72.22 (7)
C2—Ru1—P1	115.10 (3)	C5—C4—Ru1	67.54 (7)
C4—Ru1—P1	158.87 (4)	C3—C4—H4	120.3
C3—Ru1—P1	152.44 (4)	C5—C4—H4	120.3
C5—Ru1—Cl1	151.18 (4)	Ru1—C4—H4	133
C1—Ru1—Cl1	120.39 (4)	C16—C17—C18	111.25 (10)
C6—Ru1—Cl1	158.52 (4)	C16—C17—H17A	109.4
C2—Ru1—Cl1	92.13 (4)	C18—C17—H17A	109.4
C4—Ru1—Cl1	114.00 (4)	C16—C17—H17B	109.4
C3—Ru1—Cl1	90.67 (4)	C18—C17—H17B	109.4
P1—Ru1—Cl1	87.124 (11)	H17A—C17—H17B	108
C5—Ru1—Cl2	86.78 (4)	C9—C8—C7	111.20 (10)
C1—Ru1—Cl2	151.53 (4)	C9—C8—H8A	109.4
C6—Ru1—Cl2	113.39 (4)	C7—C8—H8A	109.4
C2—Ru1—Cl2	153.91 (3)	C9—C8—H8B	109.4
C4—Ru1—Cl2	89.50 (4)	C7—C8—H8B	109.4
C3—Ru1—Cl2	116.42 (3)	H8A—C8—H8B	108
P1—Ru1—Cl2	90.969 (10)	C28—C29—C30	119.92 (14)
Cl1—Ru1—Cl2	88.071 (11)	C28—C29—H29	120
C19—P1—C13	103.21 (5)	C30—C29—H29	120
C19—P1—C7	110.18 (5)	C30—C25—C26	120.13 (14)
C13—P1—C7	106.93 (5)	C30—C25—H25	119.9
C19—P1—Ru1	109.13 (4)	C26—C25—H25	119.9
C13—P1—Ru1	113.89 (4)	C9—C10—C11	111.01 (11)
C7—P1—Ru1	113.03 (4)	C9—C10—H10A	109.4
C22—C21—C20	120.56 (12)	C11—C10—H10A	109.4
C22—C21—H21	119.7	C9—C10—H10B	109.4
C20—C21—H21	119.7	C11—C10—H10B	109.4
C23—C24—C19	121.02 (12)	H10A—C10—H10B	108
C23—C24—H24	119.5	C25—C30—C29	119.91 (14)
C19—C24—H24	119.5	C25—C30—H30	120
C12—C7—C8	110.59 (9)	C29—C30—H30	120
C12—C7—P1	114.10 (8)	C10—C11—C12	111.49 (12)
C8—C7—P1	115.61 (8)	C10—C11—H11A	109.3
C12—C7—H7	105.1	C12—C11—H11A	109.3
C8—C7—H7	105.1	C10—C11—H11B	109.3
P1—C7—H7	105.1	C12—C11—H11B	109.3
C4—C3—C2	120.40 (12)	H11A—C11—H11B	108
C4—C3—Ru1	72.14 (7)	C26—C27—C28	119.83 (14)
C2—C3—Ru1	68.39 (7)	C26—C27—H27	120.1
C4—C3—H3	119.8	C28—C27—H27	120.1
C2—C3—H3	119.8	C27—C28—C29	120.08 (14)
Ru1—C3—H3	132.8	C27—C28—H28	120
C20—C19—C24	118.14 (11)	C29—C28—H28	120
C20—C19—P1	124.07 (10)	C25—C26—C27	120.12 (14)
C24—C19—P1	117.23 (9)	C25—C26—H26	119.9
C11—C12—C7	110.46 (10)	C27—C26—H26	119.9
C11—C12—H12A	109.6	C17—C18—C13	109.57 (10)
C7—C12—H12A	109.6	C17—C18—H18A	109.8
C11—C12—H12B	109.6	C13—C18—H18A	109.8
C7—C12—H12B	109.6	C17—C18—H18B	109.8
H12A—C12—H12B	108.1	C13—C18—H18B	109.8
C16—C15—C14	111.35 (10)	H18A—C18—H18B	108.2
C16—C15—H15A	109.4	C15—C14—C13	109.76 (10)
C14—C15—H15A	109.4	C15—C14—H14A	109.7
C16—C15—H15B	109.4	C13—C14—H14A	109.7
C14—C15—H15B	109.4	C15—C14—H14B	109.7
H15A—C15—H15B	108	C13—C14—H14B	109.7
C5—C6—C1	119.38 (12)	H14A—C14—H14B	108.2
C5—C6—Ru1	70.72 (7)	C15—C16—C17	111.11 (10)
C1—C6—Ru1	70.89 (7)	C15—C16—H16A	109.4
C5—C6—H6	120.3	C17—C16—H16A	109.4
C1—C6—H6	120.3	C15—C16—H16B	109.4
Ru1—C6—H6	130.6	C17—C16—H16B	109.4
C6—C5—C4	120.66 (13)	H16A—C16—H16B	108
C6—C5—Ru1	71.55 (7)	C32—C31—C33	119.98 (14)
C4—C5—Ru1	74.79 (7)	C32—C31—H31	120
C6—C5—H5	119.7	C33—C31—H31	120
C4—C5—H5	119.7	C31—C32—C33i	120.33 (14)
Ru1—C5—H5	125.8	C31—C32—H32	119.8
C10—C9—C8	111.74 (11)	C33i—C32—H32	119.8
C10—C9—H9A	109.3	C32i—C33—C31	119.69 (15)
C8—C9—H9A	109.3	C32i—C33—H33	120.2
C10—C9—H9B	109.3	C31—C33—H33	120.2
C8—C9—H9B	109.3
C18—C13—P1—C19	169.93 (8)	P1—Ru1—C5—C4	−177.46 (6)
C14—C13—P1—C19	40.18 (10)	Cl1—Ru1—C5—C4	13.27 (13)
C18—C13—P1—C7	53.70 (9)	Cl2—Ru1—C5—C4	93.36 (7)
C14—C13—P1—C7	−76.05 (10)	C19—C24—C23—C22	−0.8 (2)
C18—C13—P1—Ru1	−71.90 (8)	C4—C3—C2—C1	3.99 (18)
C14—C13—P1—Ru1	158.35 (8)	Ru1—C3—C2—C1	56.04 (10)
C5—Ru1—P1—C19	21.52 (6)	C4—C3—C2—Ru1	−52.05 (11)
C1—Ru1—P1—C19	−43.22 (6)	C5—Ru1—C2—C1	−66.72 (8)
C6—Ru1—P1—C19	−5.15 (6)	C6—Ru1—C2—C1	−29.53 (8)
C2—Ru1—P1—C19	−72.63 (6)	C4—Ru1—C2—C1	−103.39 (9)
C4—Ru1—P1—C19	17.21 (11)	C3—Ru1—C2—C1	−130.37 (12)
C3—Ru1—P1—C19	−77.71 (9)	P1—Ru1—C2—C1	53.49 (8)
Cl1—Ru1—P1—C19	−163.64 (4)	Cl1—Ru1—C2—C1	141.32 (7)
Cl2—Ru1—P1—C19	108.34 (4)	Cl2—Ru1—C2—C1	−128.72 (8)
C5—Ru1—P1—C13	−93.20 (6)	C5—Ru1—C2—C3	63.64 (8)
C1—Ru1—P1—C13	−157.94 (6)	C1—Ru1—C2—C3	130.37 (12)
C6—Ru1—P1—C13	−119.87 (6)	C6—Ru1—C2—C3	100.84 (9)
C2—Ru1—P1—C13	172.65 (6)	C4—Ru1—C2—C3	26.98 (8)
C4—Ru1—P1—C13	−97.51 (11)	P1—Ru1—C2—C3	−176.14 (7)
C3—Ru1—P1—C13	167.57 (8)	Cl1—Ru1—C2—C3	−88.32 (8)
Cl1—Ru1—P1—C13	81.64 (4)	Cl2—Ru1—C2—C3	1.64 (14)
Cl2—Ru1—P1—C13	−6.38 (4)	C3—C2—C1—C6	−3.71 (18)
C5—Ru1—P1—C7	144.49 (6)	Ru1—C2—C1—C6	53.97 (10)
C1—Ru1—P1—C7	79.75 (6)	C3—C2—C1—Ru1	−57.67 (10)
C6—Ru1—P1—C7	117.83 (6)	C5—C6—C1—C2	−0.86 (18)
C2—Ru1—P1—C7	50.34 (6)	Ru1—C6—C1—C2	−54.27 (10)
C4—Ru1—P1—C7	140.19 (11)	C5—C6—C1—Ru1	53.41 (10)
C3—Ru1—P1—C7	45.26 (9)	C5—Ru1—C1—C2	102.95 (9)
Cl1—Ru1—P1—C7	−40.66 (4)	C6—Ru1—C1—C2	132.15 (11)
Cl2—Ru1—P1—C7	−128.68 (4)	C4—Ru1—C1—C2	65.31 (8)
C19—P1—C7—C12	80.39 (9)	C3—Ru1—C1—C2	30.20 (8)
C13—P1—C7—C12	−168.11 (8)	P1—Ru1—C1—C2	−133.29 (7)
Ru1—P1—C7—C12	−41.99 (9)	Cl1—Ru1—C1—C2	−46.40 (8)
C19—P1—C7—C8	−49.53 (10)	Cl2—Ru1—C1—C2	133.96 (7)
C13—P1—C7—C8	61.97 (10)	C5—Ru1—C1—C6	−29.20 (7)
Ru1—P1—C7—C8	−171.91 (7)	C2—Ru1—C1—C6	−132.15 (11)
C5—Ru1—C3—C4	28.75 (8)	C4—Ru1—C1—C6	−66.84 (8)
C1—Ru1—C3—C4	104.07 (9)	C3—Ru1—C1—C6	−101.94 (8)
C6—Ru1—C3—C4	66.10 (8)	P1—Ru1—C1—C6	94.57 (7)
C2—Ru1—C3—C4	134.39 (12)	Cl1—Ru1—C1—C6	−178.54 (6)
P1—Ru1—C3—C4	141.96 (7)	Cl2—Ru1—C1—C6	1.81 (12)
Cl1—Ru1—C3—C4	−132.98 (7)	C24—C19—C20—C21	0.37 (18)
Cl2—Ru1—C3—C4	−44.80 (8)	P1—C19—C20—C21	−170.69 (10)
C5—Ru1—C3—C2	−105.64 (9)	C22—C21—C20—C19	−0.27 (19)
C1—Ru1—C3—C2	−30.32 (8)	C20—C21—C22—C23	−0.4 (2)
C6—Ru1—C3—C2	−68.29 (8)	C24—C23—C22—C21	0.9 (2)
C4—Ru1—C3—C2	−134.39 (12)	C2—C3—C4—C5	0.32 (18)
P1—Ru1—C3—C2	7.57 (13)	Ru1—C3—C4—C5	−50.06 (10)
Cl1—Ru1—C3—C2	92.63 (8)	C2—C3—C4—Ru1	50.38 (11)
Cl2—Ru1—C3—C2	−179.19 (7)	C6—C5—C4—C3	−4.96 (18)
C23—C24—C19—C20	0.15 (18)	Ru1—C5—C4—C3	52.19 (11)
C23—C24—C19—P1	171.83 (10)	C6—C5—C4—Ru1	−57.14 (10)
C13—P1—C19—C20	−142.05 (10)	C5—Ru1—C4—C3	−133.75 (12)
C7—P1—C19—C20	−28.16 (12)	C1—Ru1—C4—C3	−65.49 (8)
Ru1—P1—C19—C20	96.50 (10)	C6—Ru1—C4—C3	−103.44 (9)
C13—P1—C19—C24	46.81 (11)	C2—Ru1—C4—C3	−28.28 (8)
C7—P1—C19—C24	160.70 (9)	P1—Ru1—C4—C3	−127.73 (10)
Ru1—P1—C19—C24	−74.64 (10)	Cl1—Ru1—C4—C3	53.20 (8)
C8—C7—C12—C11	−56.30 (14)	Cl2—Ru1—C4—C3	140.87 (7)
P1—C7—C12—C11	171.32 (9)	C1—Ru1—C4—C5	68.27 (8)
C1—Ru1—C6—C5	−132.16 (11)	C6—Ru1—C4—C5	30.32 (8)
C2—Ru1—C6—C5	−102.99 (9)	C2—Ru1—C4—C5	105.47 (9)
C4—Ru1—C6—C5	−30.27 (8)	C3—Ru1—C4—C5	133.75 (12)
C3—Ru1—C6—C5	−65.51 (8)	P1—Ru1—C4—C5	6.03 (15)
P1—Ru1—C6—C5	141.19 (7)	Cl1—Ru1—C4—C5	−173.04 (7)
Cl1—Ru1—C6—C5	−128.73 (9)	Cl2—Ru1—C4—C5	−85.38 (8)
Cl2—Ru1—C6—C5	48.78 (8)	C10—C9—C8—C7	−55.01 (15)
C5—Ru1—C6—C1	132.16 (11)	C12—C7—C8—C9	55.45 (14)
C2—Ru1—C6—C1	29.17 (7)	P1—C7—C8—C9	−172.95 (9)
C4—Ru1—C6—C1	101.89 (8)	C8—C9—C10—C11	55.02 (17)
C3—Ru1—C6—C1	66.65 (7)	C26—C25—C30—C29	0.5 (2)
P1—Ru1—C6—C1	−86.65 (7)	C28—C29—C30—C25	0.2 (2)
Cl1—Ru1—C6—C1	3.44 (14)	C9—C10—C11—C12	−56.16 (17)
Cl2—Ru1—C6—C1	−179.06 (6)	C7—C12—C11—C10	56.94 (15)
C1—C6—C5—C4	5.21 (18)	C26—C27—C28—C29	0.3 (2)
Ru1—C6—C5—C4	58.71 (11)	C30—C29—C28—C27	−0.6 (2)
C1—C6—C5—Ru1	−53.49 (10)	C30—C25—C26—C27	−0.7 (2)
C1—Ru1—C5—C6	29.50 (8)	C28—C27—C26—C25	0.3 (2)
C2—Ru1—C5—C6	66.63 (8)	C16—C17—C18—C13	57.64 (13)
C4—Ru1—C5—C6	130.38 (12)	C14—C13—C18—C17	−59.41 (12)
C3—Ru1—C5—C6	103.09 (9)	P1—C13—C18—C17	166.81 (8)
P1—Ru1—C5—C6	−47.08 (9)	C16—C15—C14—C13	−56.64 (13)
Cl1—Ru1—C5—C6	143.65 (7)	C18—C13—C14—C15	58.94 (13)
Cl2—Ru1—C5—C6	−136.26 (8)	P1—C13—C14—C15	−170.54 (8)
C1—Ru1—C5—C4	−100.88 (9)	C14—C15—C16—C17	55.08 (13)
C6—Ru1—C5—C4	−130.38 (12)	C18—C17—C16—C15	−55.60 (13)
C2—Ru1—C5—C4	−63.75 (8)	C33—C31—C32—C33i	−0.2 (2)
C3—Ru1—C5—C4	−27.30 (8)	C32—C31—C33—C32i	0.2 (2)

D—H···A	D—H	H···A	D···A	D—H···A
C3—H3···Cl2ii	0.95	2.76	3.6307 (13)	153
C4—H4···Cl1ii	0.95	2.7	3.6209 (13)	163
C6—H6···Cg1	0.95	2.78	3.5086 (14)	135
C2—H2···Cg2iii	0.95	2.73	3.5869 (15)	150

Table 1

Hydrogen-bond geometry (Å, °)

Cg1 and Cg2 are the centroids of the C19–C24 and C31–C33/C31′–C33′) benzene rings.

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C3—H3⋯Cl2i	0.95	2.76	3.6307 (13)	153
C4—H4⋯Cl1i	0.95	2.7	3.6209 (13)	163
C6—H6⋯Cg1	0.95	2.78	3.5086 (14)	135
C2—H2⋯Cg2ii	0.95	2.73	3.5869 (15)	150

Symmetry codes: (i) ; (ii) .