(η(6)-Benzene)-(benzyl-diphenyl-phos-phane)dichloridoruthenium(II).

In the title compound, [RuCl(2)(C(6)H(6))(C(19)H(17)P)], the Ru(II) atom has a distorted pseudo-octa-hedral coordination environment with the metrical parameters around the metallic core as Ru-centroid(η(6)-benzene) = 1.6894 (11) Å, Ru-P = 2.3466 (6), Ru-Cl(avg.) = 2.4127 (7) Å; Cl-Ru-Cl = 88.07 (2) and Cl-Ru-P = 82.77 (2), 87.65 (2)°. The effective cone angle for the benzyl-diphenyl-phosphane was calculated to be 143°. In the crystal C-H⋯Cl and C-H⋯π inter-actions are observed.

Related literature

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

Experimental

Crystal data

[RuCl2(C6H6)(C19H17P)]

M = 526.37

Orthorhombic,

a = 16.8415 (9) Å

b = 14.1497 (7) Å

c = 18.6919 (8) Å

V = 4454.3 (4) Å3

Z = 8

Mo Kα radiation

μ = 1.03 mm−1

T = 100 K

0.09 × 0.03 × 0.01 mm

Data collection

Bruker APEX DUO 4K-CCD diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2008 ▶) T min = 0.429, T max = 0.629

34735 measured reflections

5544 independent reflections

4056 reflections with I > 2σ(I)

R int = 0.063

Refinement

R[F 2 > 2σ(F 2)] = 0.032

wR(F 2) = 0.069

S = 1.01

5544 reflections

262 parameters

H-atom parameters constrained

Δρmax = 0.44 e Å−3

Δρmin = −0.58 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 ▶).

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S1600536812037154/bt6823sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536812037154/bt6823Isup2.hkl

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

[RuCl2(C6H6)(C19H17P)]	F(000) = 2128
Mr = 526.37	Dx = 1.57 Mg m−3
Orthorhombic, Pbca	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ac 2ab	Cell parameters from 5707 reflections
a = 16.8415 (9) Å	θ = 2.2–28.1°
b = 14.1497 (7) Å	µ = 1.03 mm−1
c = 18.6919 (8) Å	T = 100 K
V = 4454.3 (4) Å3	Plate, red
Z = 8	0.09 × 0.03 × 0.01 mm

Bruker APEX DUO 4K-CCD diffractometer	5544 independent reflections
Radiation source: sealed tube	4056 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.063
Detector resolution: 8.4 pixels mm-1	θmax = 28.3°, θmin = 2.2°
φ and ω scans	h = −10→22
Absorption correction: multi-scan (SADABS; Bruker, 2008)	k = −18→18
Tmin = 0.429, Tmax = 0.629	l = −24→24
34735 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)] = 0.032	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.069	H-atom parameters constrained
S = 1.01	w = 1/[σ2(Fo2) + (0.024P)2 + 3.1419P] where P = (Fo2 + 2Fc2)/3
5544 reflections	(Δ/σ)max = 0.005
262 parameters	Δρmax = 0.44 e Å−3
0 restraints	Δρmin = −0.58 e Å−3

Experimental. The intensity data was collected on a Bruker Apex DUO 4 K CCD diffractometer using an exposure time of 40 s/frame. A total of 972 frames were collected with a frame width of 0.5° covering up to θ = 28.3° with 100% 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
Ru1	0.192720 (13)	0.729519 (13)	1.097642 (10)	0.01308 (6)
Cl1	0.31341 (4)	0.65099 (4)	1.13353 (3)	0.01973 (14)
Cl2	0.12848 (4)	0.57711 (4)	1.09754 (3)	0.01605 (13)
P1	0.22367 (4)	0.68784 (4)	0.97937 (3)	0.01223 (14)
C1	0.1603 (2)	0.86916 (17)	1.06111 (14)	0.0241 (7)
H1	0.1636	0.894	1.014	0.029*
C2	0.22515 (19)	0.87954 (18)	1.10820 (14)	0.0240 (7)
H2	0.2714	0.9128	1.0935	0.029*
C3	0.22054 (19)	0.84011 (18)	1.17715 (14)	0.0224 (6)
H3	0.2649	0.8444	1.2083	0.027*
C4	0.15104 (19)	0.79438 (18)	1.20056 (14)	0.0232 (7)
H4	0.1474	0.7705	1.2479	0.028*
C5	0.08725 (19)	0.78461 (19)	1.15297 (15)	0.0260 (7)
H5	0.0408	0.752	1.1679	0.031*
C6	0.0910 (2)	0.82252 (19)	1.08314 (15)	0.0264 (7)
H6	0.0471	0.8165	1.0515	0.032*
C7	0.26500 (17)	0.56772 (16)	0.97117 (12)	0.0151 (6)
H7A	0.3014	0.5571	1.012	0.018*
H7B	0.2208	0.522	0.9759	0.018*
C8	0.30938 (17)	0.54528 (16)	0.90309 (12)	0.0151 (5)
C9	0.26901 (17)	0.51027 (16)	0.84315 (13)	0.0169 (6)
H9	0.2131	0.5017	0.8449	0.02*
C10	0.31070 (19)	0.48790 (17)	0.78088 (13)	0.0205 (6)
H10	0.2833	0.4633	0.7405	0.025*
C11	0.3918 (2)	0.50152 (18)	0.77798 (14)	0.0231 (7)
H11	0.4199	0.4871	0.7353	0.028*
C12	0.43254 (19)	0.53603 (19)	0.83694 (15)	0.0255 (7)
H12	0.4884	0.545	0.8348	0.031*
C13	0.39101 (18)	0.55751 (18)	0.89933 (14)	0.0210 (6)
H13	0.4189	0.5808	0.9398	0.025*
C14	0.29770 (16)	0.76094 (16)	0.93506 (12)	0.0131 (5)
C15	0.29935 (17)	0.76972 (17)	0.86005 (12)	0.0169 (6)
H15	0.2587	0.7413	0.8321	0.02*
C16	0.35968 (17)	0.81950 (17)	0.82660 (13)	0.0166 (6)
H16	0.3601	0.8257	0.776	0.02*
C17	0.41946 (17)	0.86018 (17)	0.86719 (14)	0.0180 (6)
H17	0.4605	0.8949	0.8443	0.022*
C18	0.41973 (17)	0.85044 (17)	0.94114 (13)	0.0173 (6)
H18	0.4615	0.8774	0.9686	0.021*
C19	0.35912 (17)	0.80140 (17)	0.97485 (13)	0.0170 (6)
H19	0.3594	0.7952	1.0255	0.02*
C20	0.13550 (17)	0.69210 (17)	0.92313 (12)	0.0140 (5)
C21	0.10851 (17)	0.77773 (17)	0.89283 (13)	0.0168 (6)
H21	0.1402	0.8331	0.8966	0.02*
C22	0.03634 (18)	0.78158 (19)	0.85764 (13)	0.0203 (6)
H22	0.0186	0.8398	0.8381	0.024*
C23	−0.01037 (18)	0.70135 (19)	0.85061 (13)	0.0198 (6)
H23	−0.0597	0.7044	0.8261	0.024*
C24	0.01564 (17)	0.61655 (18)	0.87968 (13)	0.0180 (6)
H24	−0.0158	0.5612	0.8746	0.022*
C25	0.08700 (17)	0.61219 (17)	0.91598 (12)	0.0154 (6)
H25	0.1035	0.554	0.9365	0.018*

	U11	U22	U33	U12	U13	U23
Ru1	0.01380 (12)	0.01403 (9)	0.01141 (9)	−0.00318 (9)	0.00057 (9)	−0.00071 (7)
Cl1	0.0162 (4)	0.0272 (3)	0.0158 (3)	−0.0018 (3)	−0.0033 (3)	0.0008 (2)
Cl2	0.0149 (4)	0.0154 (3)	0.0178 (3)	−0.0033 (2)	0.0016 (3)	0.0020 (2)
P1	0.0122 (4)	0.0123 (3)	0.0122 (3)	−0.0016 (3)	−0.0003 (3)	0.0001 (2)
C1	0.040 (2)	0.0133 (12)	0.0190 (13)	0.0028 (12)	0.0008 (13)	−0.0013 (10)
C2	0.0279 (19)	0.0167 (12)	0.0275 (14)	−0.0081 (12)	0.0095 (13)	−0.0051 (10)
C3	0.0247 (19)	0.0203 (12)	0.0221 (13)	−0.0020 (12)	−0.0030 (12)	−0.0091 (10)
C4	0.031 (2)	0.0229 (13)	0.0159 (12)	−0.0034 (12)	0.0079 (12)	−0.0042 (10)
C5	0.0194 (18)	0.0239 (14)	0.0348 (15)	−0.0010 (13)	0.0085 (13)	−0.0097 (12)
C6	0.028 (2)	0.0224 (14)	0.0291 (15)	0.0073 (13)	−0.0067 (13)	−0.0119 (11)
C7	0.0163 (17)	0.0157 (11)	0.0131 (11)	0.0017 (10)	−0.0016 (11)	0.0004 (9)
C8	0.0186 (16)	0.0118 (10)	0.0151 (10)	0.0005 (11)	0.0002 (12)	0.0009 (9)
C9	0.0155 (17)	0.0139 (11)	0.0212 (12)	−0.0005 (11)	−0.0021 (11)	0.0003 (9)
C10	0.0289 (19)	0.0163 (12)	0.0164 (11)	0.0036 (12)	−0.0048 (13)	−0.0018 (9)
C11	0.031 (2)	0.0178 (12)	0.0207 (13)	0.0012 (12)	0.0110 (13)	−0.0011 (10)
C12	0.0176 (18)	0.0255 (14)	0.0335 (15)	−0.0042 (13)	0.0115 (14)	−0.0064 (12)
C13	0.0176 (17)	0.0218 (13)	0.0234 (13)	−0.0026 (11)	−0.0003 (13)	−0.0066 (11)
C14	0.0121 (16)	0.0135 (10)	0.0137 (10)	0.0012 (10)	−0.0003 (10)	0.0007 (9)
C15	0.0182 (17)	0.0170 (11)	0.0156 (11)	0.0012 (11)	−0.0015 (11)	−0.0012 (9)
C16	0.0161 (17)	0.0188 (12)	0.0151 (11)	0.0038 (11)	0.0032 (11)	0.0040 (10)
C17	0.0124 (16)	0.0166 (12)	0.0248 (13)	0.0017 (11)	0.0060 (12)	0.0040 (10)
C18	0.0132 (16)	0.0175 (12)	0.0211 (12)	−0.0015 (11)	−0.0037 (12)	−0.0013 (10)
C19	0.0158 (17)	0.0199 (12)	0.0154 (11)	0.0006 (11)	−0.0013 (11)	0.0004 (9)
C20	0.0141 (16)	0.0168 (11)	0.0111 (10)	−0.0025 (11)	0.0018 (10)	−0.0023 (9)
C21	0.0157 (16)	0.0151 (11)	0.0196 (12)	−0.0020 (11)	−0.0001 (11)	−0.0007 (10)
C22	0.0184 (17)	0.0208 (13)	0.0216 (12)	0.0044 (12)	−0.0030 (12)	0.0014 (10)
C23	0.0089 (16)	0.0291 (14)	0.0213 (13)	0.0005 (12)	−0.0033 (11)	−0.0032 (10)
C24	0.0143 (17)	0.0211 (12)	0.0186 (12)	−0.0035 (11)	0.0015 (12)	−0.0035 (10)
C25	0.0151 (16)	0.0156 (11)	0.0154 (11)	−0.0022 (11)	0.0011 (11)	−0.0007 (9)

Ru1—C1	2.161 (3)	C9—H9	0.95
Ru1—C6	2.177 (3)	C10—C11	1.380 (4)
Ru1—C5	2.198 (3)	C10—H10	0.95
Ru1—C2	2.201 (3)	C11—C12	1.387 (4)
Ru1—C3	2.208 (2)	C11—H11	0.95
Ru1—C4	2.244 (3)	C12—C13	1.393 (4)
Ru1—P1	2.3466 (6)	C12—H12	0.95
Ru1—Cl1	2.4116 (7)	C13—H13	0.95
Ru1—Cl2	2.4127 (6)	C14—C19	1.397 (4)
P1—C14	1.819 (3)	C14—C15	1.408 (3)
P1—C20	1.820 (3)	C15—C16	1.385 (4)
P1—C7	1.843 (2)	C15—H15	0.95
C1—C6	1.403 (4)	C16—C17	1.386 (4)
C1—C2	1.410 (4)	C16—H16	0.95
C1—H1	0.95	C17—C18	1.389 (3)
C2—C3	1.406 (4)	C17—H17	0.95
C2—H2	0.95	C18—C19	1.386 (4)
C3—C4	1.407 (4)	C18—H18	0.95
C3—H3	0.95	C19—H19	0.95
C4—C5	1.402 (4)	C20—C25	1.401 (4)
C4—H4	0.95	C20—C21	1.413 (3)
C5—C6	1.413 (4)	C21—C22	1.383 (4)
C5—H5	0.95	C21—H21	0.95
C6—H6	0.95	C22—C23	1.387 (4)
C7—C8	1.510 (3)	C22—H22	0.95
C7—H7A	0.99	C23—C24	1.388 (4)
C7—H7B	0.99	C23—H23	0.95
C8—C13	1.387 (4)	C24—C25	1.382 (4)
C8—C9	1.401 (3)	C24—H24	0.95
C9—C10	1.396 (4)	C25—H25	0.95
C1—Ru1—C6	37.73 (11)	C4—C5—H5	119.5
C1—Ru1—C5	67.68 (11)	C6—C5—H5	119.5
C6—Ru1—C5	37.66 (10)	Ru1—C5—H5	129.1
C1—Ru1—C2	37.72 (11)	C1—C6—C5	119.1 (3)
C6—Ru1—C2	67.88 (12)	C1—C6—Ru1	70.48 (17)
C5—Ru1—C2	79.41 (11)	C5—C6—Ru1	71.96 (17)
C1—Ru1—C3	67.56 (10)	C1—C6—H6	120.4
C6—Ru1—C3	79.78 (11)	C5—C6—H6	120.4
C5—Ru1—C3	66.65 (11)	Ru1—C6—H6	129.4
C2—Ru1—C3	37.20 (9)	C8—C7—P1	116.81 (16)
C1—Ru1—C4	79.51 (10)	C8—C7—H7A	108.1
C6—Ru1—C4	67.26 (11)	P1—C7—H7A	108.1
C5—Ru1—C4	36.77 (11)	C8—C7—H7B	108.1
C2—Ru1—C4	66.81 (10)	P1—C7—H7B	108.1
C3—Ru1—C4	36.84 (10)	H7A—C7—H7B	107.3
C1—Ru1—P1	89.32 (7)	C13—C8—C9	119.0 (2)
C6—Ru1—P1	102.09 (7)	C13—C8—C7	120.5 (2)
C5—Ru1—P1	135.38 (8)	C9—C8—C7	120.5 (3)
C2—Ru1—P1	105.77 (7)	C10—C9—C8	120.2 (3)
C3—Ru1—P1	139.90 (8)	C10—C9—H9	119.9
C4—Ru1—P1	168.48 (8)	C8—C9—H9	119.9
C1—Ru1—Cl1	136.24 (9)	C11—C10—C9	119.9 (2)
C6—Ru1—Cl1	167.51 (7)	C11—C10—H10	120
C5—Ru1—Cl1	135.53 (8)	C9—C10—H10	120
C2—Ru1—Cl1	102.14 (9)	C10—C11—C12	120.5 (2)
C3—Ru1—Cl1	87.73 (8)	C10—C11—H11	119.7
C4—Ru1—Cl1	102.33 (8)	C12—C11—H11	119.7
P1—Ru1—Cl1	87.65 (2)	C11—C12—C13	119.5 (3)
C1—Ru1—Cl2	134.73 (9)	C11—C12—H12	120.2
C6—Ru1—Cl2	100.79 (8)	C13—C12—H12	120.2
C5—Ru1—Cl2	87.42 (8)	C8—C13—C12	120.8 (3)
C2—Ru1—Cl2	166.78 (8)	C8—C13—H13	119.6
C3—Ru1—Cl2	136.81 (7)	C12—C13—H13	119.6
C4—Ru1—Cl2	103.06 (7)	C19—C14—C15	118.6 (2)
P1—Ru1—Cl2	82.77 (2)	C19—C14—P1	119.88 (18)
Cl1—Ru1—Cl2	88.07 (2)	C15—C14—P1	121.1 (2)
C14—P1—C20	106.10 (11)	C16—C15—C14	120.6 (3)
C14—P1—C7	103.15 (12)	C16—C15—H15	119.7
C20—P1—C7	106.90 (12)	C14—C15—H15	119.7
C14—P1—Ru1	115.99 (8)	C15—C16—C17	119.8 (2)
C20—P1—Ru1	110.77 (8)	C15—C16—H16	120.1
C7—P1—Ru1	113.20 (8)	C17—C16—H16	120.1
C6—C1—C2	120.7 (3)	C16—C17—C18	120.4 (3)
C6—C1—Ru1	71.78 (16)	C16—C17—H17	119.8
C2—C1—Ru1	72.68 (15)	C18—C17—H17	119.8
C6—C1—H1	119.7	C19—C18—C17	120.0 (3)
C2—C1—H1	119.7	C19—C18—H18	120
Ru1—C1—H1	128.1	C17—C18—H18	120
C3—C2—C1	119.2 (3)	C18—C19—C14	120.6 (2)
C3—C2—Ru1	71.69 (15)	C18—C19—H19	119.7
C1—C2—Ru1	69.60 (15)	C14—C19—H19	119.7
C3—C2—H2	120.4	C25—C20—C21	117.8 (2)
C1—C2—H2	120.4	C25—C20—P1	120.25 (19)
Ru1—C2—H2	130.9	C21—C20—P1	121.50 (19)
C2—C3—C4	120.9 (3)	C22—C21—C20	120.5 (2)
C2—C3—Ru1	71.11 (15)	C22—C21—H21	119.8
C4—C3—Ru1	72.96 (15)	C20—C21—H21	119.8
C2—C3—H3	119.6	C21—C22—C23	120.7 (2)
C4—C3—H3	119.6	C21—C22—H22	119.6
Ru1—C3—H3	128.7	C23—C22—H22	119.6
C5—C4—C3	119.0 (3)	C22—C23—C24	119.4 (3)
C5—C4—Ru1	69.83 (15)	C22—C23—H23	120.3
C3—C4—Ru1	70.20 (14)	C24—C23—H23	120.3
C5—C4—H4	120.5	C25—C24—C23	120.4 (2)
C3—C4—H4	120.5	C25—C24—H24	119.8
Ru1—C4—H4	132.4	C23—C24—H24	119.8
C4—C5—C6	121.0 (3)	C24—C25—C20	121.2 (2)
C4—C5—Ru1	73.40 (18)	C24—C25—H25	119.4
C6—C5—Ru1	70.37 (17)	C20—C25—H25	119.4
C1—Ru1—P1—C14	57.32 (13)	C5—Ru1—C4—C3	−133.0 (3)
C6—Ru1—P1—C14	93.09 (12)	C2—Ru1—C4—C3	−29.14 (17)
C5—Ru1—P1—C14	113.77 (14)	P1—Ru1—C4—C3	−80.7 (5)
C2—Ru1—P1—C14	22.94 (13)	Cl1—Ru1—C4—C3	68.93 (17)
C3—Ru1—P1—C14	4.66 (16)	Cl2—Ru1—C4—C3	159.82 (16)
C4—Ru1—P1—C14	71.4 (4)	C3—C4—C5—C6	−2.1 (4)
Cl1—Ru1—P1—C14	−79.02 (9)	Ru1—C4—C5—C6	−54.0 (2)
Cl2—Ru1—P1—C14	−167.37 (10)	C3—C4—C5—Ru1	51.9 (2)
C1—Ru1—P1—C20	−63.67 (12)	C1—Ru1—C5—C4	−102.74 (18)
C6—Ru1—P1—C20	−27.90 (12)	C6—Ru1—C5—C4	−132.6 (2)
C5—Ru1—P1—C20	−7.22 (14)	C2—Ru1—C5—C4	−65.22 (17)
C2—Ru1—P1—C20	−98.05 (12)	C3—Ru1—C5—C4	−28.53 (16)
C3—Ru1—P1—C20	−116.32 (15)	P1—Ru1—C5—C4	−167.01 (12)
C4—Ru1—P1—C20	−49.6 (4)	Cl1—Ru1—C5—C4	31.4 (2)
Cl1—Ru1—P1—C20	160.00 (9)	Cl2—Ru1—C5—C4	115.99 (15)
Cl2—Ru1—P1—C20	71.65 (9)	C1—Ru1—C5—C6	29.85 (16)
C1—Ru1—P1—C7	176.28 (13)	C2—Ru1—C5—C6	67.37 (17)
C6—Ru1—P1—C7	−147.95 (13)	C3—Ru1—C5—C6	104.06 (18)
C5—Ru1—P1—C7	−127.27 (15)	C4—Ru1—C5—C6	132.6 (2)
C2—Ru1—P1—C7	141.91 (13)	P1—Ru1—C5—C6	−34.4 (2)
C3—Ru1—P1—C7	123.63 (16)	Cl1—Ru1—C5—C6	163.98 (13)
C4—Ru1—P1—C7	−169.6 (4)	Cl2—Ru1—C5—C6	−111.41 (16)
Cl1—Ru1—P1—C7	39.95 (10)	C2—C1—C6—C5	−1.0 (4)
Cl2—Ru1—P1—C7	−48.40 (10)	Ru1—C1—C6—C5	55.0 (2)
C5—Ru1—C1—C6	−29.80 (15)	C2—C1—C6—Ru1	−56.0 (2)
C2—Ru1—C1—C6	−131.7 (2)	C4—C5—C6—C1	1.1 (4)
C3—Ru1—C1—C6	−102.70 (17)	Ru1—C5—C6—C1	−54.3 (2)
C4—Ru1—C1—C6	−66.23 (16)	C4—C5—C6—Ru1	55.4 (2)
P1—Ru1—C1—C6	110.94 (15)	C5—Ru1—C6—C1	131.2 (2)
Cl1—Ru1—C1—C6	−163.16 (12)	C2—Ru1—C6—C1	29.54 (15)
Cl2—Ru1—C1—C6	31.82 (19)	C3—Ru1—C6—C1	66.38 (16)
C6—Ru1—C1—C2	131.7 (2)	C4—Ru1—C6—C1	102.65 (17)
C5—Ru1—C1—C2	101.90 (18)	P1—Ru1—C6—C1	−72.76 (15)
C3—Ru1—C1—C2	29.00 (16)	Cl1—Ru1—C6—C1	67.9 (4)
C4—Ru1—C1—C2	65.47 (17)	Cl2—Ru1—C6—C1	−157.58 (14)
P1—Ru1—C1—C2	−117.36 (16)	C1—Ru1—C6—C5	−131.2 (2)
Cl1—Ru1—C1—C2	−31.5 (2)	C2—Ru1—C6—C5	−101.65 (18)
Cl2—Ru1—C1—C2	163.52 (13)	C3—Ru1—C6—C5	−64.82 (17)
C6—C1—C2—C3	1.8 (4)	C4—Ru1—C6—C5	−28.54 (16)
Ru1—C1—C2—C3	−53.7 (2)	P1—Ru1—C6—C5	156.05 (15)
C6—C1—C2—Ru1	55.5 (2)	Cl1—Ru1—C6—C5	−63.3 (5)
C1—Ru1—C2—C3	132.2 (3)	Cl2—Ru1—C6—C5	71.22 (16)
C6—Ru1—C2—C3	102.62 (19)	C14—P1—C7—C8	−35.7 (2)
C5—Ru1—C2—C3	65.12 (19)	C20—P1—C7—C8	76.0 (2)
C4—Ru1—C2—C3	28.88 (18)	Ru1—P1—C7—C8	−161.80 (17)
P1—Ru1—C2—C3	−160.48 (16)	P1—C7—C8—C13	92.6 (3)
Cl1—Ru1—C2—C3	−69.50 (18)	P1—C7—C8—C9	−88.5 (3)
Cl2—Ru1—C2—C3	70.4 (4)	C13—C8—C9—C10	0.2 (3)
C6—Ru1—C2—C1	−29.55 (17)	C7—C8—C9—C10	−178.7 (2)
C5—Ru1—C2—C1	−67.05 (18)	C8—C9—C10—C11	−0.9 (4)
C3—Ru1—C2—C1	−132.2 (3)	C9—C10—C11—C12	1.0 (4)
C4—Ru1—C2—C1	−103.30 (19)	C10—C11—C12—C13	−0.4 (4)
P1—Ru1—C2—C1	67.34 (17)	C9—C8—C13—C12	0.4 (4)
Cl1—Ru1—C2—C1	158.33 (16)	C7—C8—C13—C12	179.3 (2)
Cl2—Ru1—C2—C1	−61.8 (4)	C11—C12—C13—C8	−0.3 (4)
C1—C2—C3—C4	−2.8 (4)	C20—P1—C14—C19	155.8 (2)
Ru1—C2—C3—C4	−55.6 (2)	C7—P1—C14—C19	−92.0 (2)
C1—C2—C3—Ru1	52.7 (2)	Ru1—P1—C14—C19	32.4 (2)
C1—Ru1—C3—C2	−29.38 (19)	C20—P1—C14—C15	−30.9 (2)
C6—Ru1—C3—C2	−66.73 (19)	C7—P1—C14—C15	81.3 (2)
C5—Ru1—C3—C2	−103.8 (2)	Ru1—P1—C14—C15	−154.40 (18)
C4—Ru1—C3—C2	−132.2 (3)	C19—C14—C15—C16	−1.6 (4)
P1—Ru1—C3—C2	29.9 (2)	P1—C14—C15—C16	−174.9 (2)
Cl1—Ru1—C3—C2	113.59 (18)	C14—C15—C16—C17	0.7 (4)
Cl2—Ru1—C3—C2	−161.65 (15)	C15—C16—C17—C18	0.7 (4)
C1—Ru1—C3—C4	102.9 (2)	C16—C17—C18—C19	−1.3 (4)
C6—Ru1—C3—C4	65.51 (18)	C17—C18—C19—C14	0.4 (4)
C5—Ru1—C3—C4	28.48 (17)	C15—C14—C19—C18	1.0 (4)
C2—Ru1—C3—C4	132.2 (3)	P1—C14—C19—C18	174.4 (2)
P1—Ru1—C3—C4	162.18 (13)	C14—P1—C20—C25	144.4 (2)
Cl1—Ru1—C3—C4	−114.17 (17)	C7—P1—C20—C25	34.8 (2)
Cl2—Ru1—C3—C4	−29.4 (2)	Ru1—P1—C20—C25	−88.9 (2)
C2—C3—C4—C5	3.0 (4)	C14—P1—C20—C21	−43.5 (2)
Ru1—C3—C4—C5	−51.8 (2)	C7—P1—C20—C21	−153.1 (2)
C2—C3—C4—Ru1	54.7 (2)	Ru1—P1—C20—C21	83.2 (2)
C1—Ru1—C4—C5	66.59 (18)	C25—C20—C21—C22	0.2 (4)
C6—Ru1—C4—C5	29.19 (17)	P1—C20—C21—C22	−172.1 (2)
C2—Ru1—C4—C5	103.85 (19)	C20—C21—C22—C23	−0.9 (4)
C3—Ru1—C4—C5	133.0 (3)	C21—C22—C23—C24	0.4 (4)
P1—Ru1—C4—C5	52.3 (5)	C22—C23—C24—C25	0.7 (4)
Cl1—Ru1—C4—C5	−158.07 (15)	C23—C24—C25—C20	−1.3 (4)
Cl2—Ru1—C4—C5	−67.19 (16)	C21—C20—C25—C24	0.9 (4)
C1—Ru1—C4—C3	−66.41 (18)	P1—C20—C25—C24	173.2 (2)
C6—Ru1—C4—C3	−103.80 (19)

D—H···A	D—H	H···A	D···A	D—H···A
C11—H11···Cl2i	0.95	2.85	3.568 (3)	133
C16—H16···Cl1ii	0.95	2.8	3.716 (3)	163
C2—H2···Cl2iii	0.95	2.87	3.733 (3)	151
C24—H24···Cl2iv	0.95	2.78	3.685 (3)	161
C21—H21···Cg1v	0.95	2.89	3.673 (3)	140
C4—H4···Cg2vi	0.95	3.00	3.789 (3)	141

Table 1

Hydrogen-bond geometry (Å, °)

Cg1 and Cg2 are the centroids of the C8–C13 and C20–C25 rings, respectively.

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C11—H11⋯Cl2i	0.95	2.85	3.568 (3)	133
C16—H16⋯Cl1ii	0.95	2.8	3.716 (3)	163
C2—H2⋯Cl2iii	0.95	2.87	3.733 (3)	151
C24—H24⋯Cl2iv	0.95	2.78	3.685 (3)	161
C21—H21⋯Cg1v	0.95	2.89	3.673 (3)	140
C4—H4⋯Cg2vi	0.95	3.00	3.789 (3)	141

Symmetry codes: (i) ; (ii) ; (iii) ; (iv) ; (v) ; (vi) .