Dichlorido(η(6)-p-cymene)(eth-oxy-diphenyl-phosphane)ruthenium(II).

The title compound, [RuCl2(C10H14)(C14H15OP)], is an Ru(II) complex in which an η(6)-p-cymene ligand, two chloride anions and the P atom of an ethoxydiphenylphosphane ligand form a piano-stool coordination environment about the central Ru(II) atom.

Related literature

For related structures [Ru(η6-p-cymene)Cl2PPh3] and [Ru(η6-p-cymene)Cl2PPhOEt2], see: Elsegood et al. (2006 ▶) and Alber­tin et al. (2010 ▶), respectively. For the application of similar complexes as nitrile hydration catalysts, see: Ahmed et al. (2009 ▶); Cavarzan et al. (2010 ▶); Cadierno et al. (2008 ▶); García-Álvarez et al. (2010 ▶, 2011 ▶); Knapp et al. (2012 ▶).

Experimental

Crystal data

[RuCl2(C10H14)(C14H15OP)]

M = 536.41

Monoclinic,

a = 13.1818 (7) Å

b = 10.8481 (6) Å

c = 16.6888 (9) Å

β = 95.060 (1)°

V = 2377.2 (2) Å3

Z = 4

Mo Kα radiation

μ = 0.97 mm−1

T = 173 K

0.23 × 0.18 × 0.06 mm

Data collection

Bruker APEX CCD area-detector diffractometer

Absorption correction: multi-scan (SADABS; Sheldrick, 1995 ▶) T min = 0.809, T max = 0.944

15739 measured reflections

5164 independent reflections

4294 reflections with I > 2σ(I)

R int = 0.028

Refinement

R[F 2 > 2σ(F 2)] = 0.030

wR(F 2) = 0.068

S = 1.05

5164 reflections

378 parameters

All H-atom parameters refined

Δρmax = 0.50 e Å−3

Δρmin = −0.47 e Å−3

Data collection: SMART (Bruker, 2000 ▶); cell refinement: SAINT (Bruker, 2000 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXTL (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL.

Click here for additional data file.

Crystal structure: contains datablock(s) I, global. DOI: 10.1107/S1600536812045461/sj5274sup1.cif

Click here for additional data file.

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536812045461/sj5274Isup2.hkl

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

[RuCl2(C10H14)(C14H15OP)]	F(000) = 1096
Mr = 536.41	Dx = 1.499 Mg m−3
Monoclinic, P21/n	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2yn	Cell parameters from 4833 reflections
a = 13.1818 (7) Å	θ = 2.2–28.2°
b = 10.8481 (6) Å	µ = 0.97 mm−1
c = 16.6888 (9) Å	T = 173 K
β = 95.060 (1)°	Plate, red
V = 2377.2 (2) Å3	0.23 × 0.18 × 0.06 mm
Z = 4

Bruker APEX CCD area-detector diffractometer	5164 independent reflections
Radiation source: fine-focus sealed tube	4294 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.028
φ and ω scans	θmax = 27.0°, θmin = 1.9°
Absorption correction: multi-scan (SADABS; Sheldrick, 1995)	h = −12→16
Tmin = 0.809, Tmax = 0.944	k = −13→12
15739 measured reflections	l = −20→21

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)] = 0.030	Hydrogen site location: difference Fourier map
wR(F2) = 0.068	All H-atom parameters refined
S = 1.05	w = 1/[σ2(Fo2) + (0.0316P)2 + 0.5053P] where P = (Fo2 + 2Fc2)/3
5164 reflections	(Δ/σ)max = 0.002
378 parameters	Δρmax = 0.50 e Å−3
0 restraints	Δρmin = −0.47 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 takeninto account individually in the estimation of e.s.d.'s in distances, anglesand torsion angles; correlations between e.s.d.'s in cell parameters are onlyused 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 andgoodness of fit S are based on F2, conventional R-factors R are basedon F, with F set to zero for negative F2. The threshold expression ofF2 > σ(F2) is used only for calculating R-factors(gt) etc. and isnot relevant to the choice of reflections for refinement. R-factors basedon 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	0.922759 (14)	0.993847 (17)	0.179893 (11)	0.02079 (7)
Cl1	0.85769 (5)	1.20143 (6)	0.16713 (4)	0.03260 (15)
Cl2	1.08699 (5)	1.06510 (6)	0.14859 (4)	0.02962 (14)
P1	0.98348 (5)	1.03105 (5)	0.31207 (4)	0.02006 (13)
O1	0.90032 (12)	1.01438 (14)	0.37705 (10)	0.0244 (4)
C1	0.76577 (19)	0.9210 (2)	0.15958 (17)	0.0346 (6)
C2	0.8041 (2)	0.9389 (3)	0.08317 (16)	0.0347 (6)
C3	0.8954 (2)	0.8889 (3)	0.06431 (16)	0.0335 (6)
C4	0.95485 (19)	0.8142 (2)	0.12134 (15)	0.0292 (6)
C5	0.9169 (2)	0.7927 (2)	0.19614 (16)	0.0287 (6)
C6	0.8235 (2)	0.8463 (2)	0.21485 (16)	0.0307 (6)
C7	0.6666 (3)	0.9770 (4)	0.1789 (3)	0.0537 (9)
C8	1.0545 (2)	0.7606 (3)	0.09785 (19)	0.0407 (7)
C9	1.0331 (3)	0.6736 (4)	0.0262 (3)	0.0617 (10)
C10	1.1180 (3)	0.6994 (4)	0.1653 (3)	0.0686 (12)
C11	1.07110 (18)	0.9129 (2)	0.35063 (14)	0.0245 (5)
C12	1.0370 (2)	0.8121 (2)	0.39239 (15)	0.0319 (6)
C13	1.1040 (2)	0.7190 (3)	0.41857 (18)	0.0444 (8)
C14	1.2050 (2)	0.7263 (3)	0.40394 (18)	0.0446 (8)
C15	1.2399 (2)	0.8264 (3)	0.36299 (17)	0.0403 (7)
C16	1.1739 (2)	0.9189 (3)	0.33660 (16)	0.0327 (6)
C17	1.05088 (17)	1.1723 (2)	0.34448 (14)	0.0238 (5)
C18	1.0912 (2)	1.1768 (3)	0.42473 (16)	0.0336 (6)
C19	1.1478 (2)	1.2776 (3)	0.45319 (18)	0.0447 (7)
C20	1.1628 (2)	1.3750 (3)	0.40183 (19)	0.0448 (8)
C21	1.1217 (2)	1.3722 (3)	0.32335 (18)	0.0384 (7)
C22	1.0657 (2)	1.2705 (2)	0.29405 (16)	0.0297 (6)
C23	0.8140 (2)	1.0977 (3)	0.37466 (17)	0.0317 (6)
C24	0.7362 (2)	1.0397 (3)	0.4228 (2)	0.0446 (8)
H2	0.770 (2)	0.993 (2)	0.0517 (17)	0.033 (8)*
H3	0.9204 (18)	0.910 (2)	0.0173 (15)	0.029 (7)*
H5	0.956 (2)	0.751 (3)	0.2361 (16)	0.038 (8)*
H6	0.8040 (18)	0.836 (2)	0.2656 (15)	0.027 (7)*
H7A	0.612 (3)	0.942 (3)	0.147 (2)	0.065 (11)*
H7B	0.649 (3)	0.982 (3)	0.234 (3)	0.093 (15)*
H7C	0.667 (2)	1.058 (3)	0.1647 (19)	0.053 (10)*
H8	1.092 (2)	0.827 (3)	0.0773 (19)	0.059 (10)*
H9A	0.991 (3)	0.704 (4)	−0.019 (3)	0.109 (18)*
H9B	0.997 (3)	0.593 (4)	0.046 (2)	0.091 (13)*
H9C	1.100 (3)	0.650 (3)	0.010 (2)	0.072 (11)*
H10A	1.179 (3)	0.667 (3)	0.148 (2)	0.072 (11)*
H10B	1.129 (3)	0.747 (4)	0.213 (3)	0.100 (15)*
H10C	1.077 (2)	0.625 (3)	0.1826 (18)	0.051 (10)*
H12	0.964 (2)	0.806 (2)	0.4018 (15)	0.036 (7)*
H13	1.0801 (19)	0.650 (2)	0.4488 (15)	0.033 (7)*
H14	1.249 (2)	0.662 (3)	0.4195 (17)	0.047 (8)*
H15	1.309 (2)	0.828 (3)	0.3514 (16)	0.042 (8)*
H16	1.192 (2)	0.985 (2)	0.3115 (16)	0.029 (7)*
H18	1.0840 (19)	1.115 (3)	0.4602 (16)	0.036 (8)*
H19	1.175 (2)	1.280 (3)	0.5067 (18)	0.052 (9)*
H20	1.202 (2)	1.435 (3)	0.4187 (16)	0.038 (8)*
H21	1.133 (2)	1.438 (3)	0.2895 (18)	0.050 (9)*
H22	1.0405 (18)	1.269 (2)	0.2397 (15)	0.026 (7)*
H23A	0.790 (2)	1.104 (3)	0.3202 (18)	0.051 (9)*
H23B	0.8364 (19)	1.178 (3)	0.3987 (15)	0.034 (7)*
H24A	0.709 (3)	0.965 (3)	0.396 (2)	0.063 (11)*
H24B	0.762 (3)	1.026 (3)	0.479 (2)	0.064 (11)*
H24C	0.681 (3)	1.094 (3)	0.4211 (19)	0.067 (11)*

	U11	U22	U33	U12	U13	U23
Ru1	0.02214 (11)	0.02052 (11)	0.01992 (10)	−0.00193 (8)	0.00301 (7)	0.00024 (7)
Cl1	0.0357 (4)	0.0261 (3)	0.0359 (3)	0.0058 (3)	0.0025 (3)	0.0038 (3)
Cl2	0.0299 (3)	0.0306 (3)	0.0299 (3)	−0.0086 (3)	0.0110 (3)	−0.0030 (3)
P1	0.0208 (3)	0.0191 (3)	0.0207 (3)	0.0008 (2)	0.0042 (2)	0.0004 (2)
O1	0.0241 (9)	0.0250 (9)	0.0251 (9)	0.0060 (7)	0.0082 (7)	0.0024 (7)
C1	0.0259 (14)	0.0330 (15)	0.0448 (16)	−0.0073 (11)	0.0019 (12)	−0.0089 (12)
C2	0.0365 (16)	0.0329 (15)	0.0321 (15)	−0.0023 (12)	−0.0104 (12)	−0.0027 (12)
C3	0.0435 (16)	0.0358 (15)	0.0214 (13)	−0.0113 (12)	0.0046 (12)	−0.0073 (11)
C4	0.0293 (14)	0.0235 (13)	0.0357 (14)	−0.0078 (10)	0.0072 (11)	−0.0098 (11)
C5	0.0335 (15)	0.0207 (13)	0.0312 (14)	−0.0063 (10)	−0.0008 (12)	−0.0019 (10)
C6	0.0343 (15)	0.0290 (14)	0.0302 (14)	−0.0125 (11)	0.0103 (12)	−0.0018 (11)
C7	0.0286 (17)	0.055 (2)	0.078 (3)	−0.0012 (15)	0.0034 (18)	−0.013 (2)
C8	0.0367 (16)	0.0306 (15)	0.0564 (19)	−0.0051 (13)	0.0132 (14)	−0.0133 (14)
C9	0.060 (2)	0.067 (3)	0.062 (2)	0.002 (2)	0.025 (2)	−0.030 (2)
C10	0.058 (3)	0.074 (3)	0.075 (3)	0.030 (2)	0.008 (2)	−0.018 (2)
C11	0.0262 (13)	0.0260 (13)	0.0215 (12)	0.0047 (10)	0.0043 (10)	−0.0031 (10)
C12	0.0340 (15)	0.0308 (14)	0.0319 (14)	0.0081 (11)	0.0091 (12)	0.0053 (11)
C13	0.0538 (19)	0.0371 (17)	0.0446 (18)	0.0145 (14)	0.0173 (15)	0.0175 (14)
C14	0.0479 (19)	0.0487 (19)	0.0380 (16)	0.0287 (15)	0.0087 (14)	0.0106 (14)
C15	0.0295 (15)	0.0545 (19)	0.0377 (16)	0.0183 (13)	0.0068 (13)	0.0021 (14)
C16	0.0306 (15)	0.0373 (16)	0.0307 (14)	0.0054 (12)	0.0060 (11)	0.0030 (12)
C17	0.0221 (12)	0.0241 (12)	0.0256 (12)	0.0005 (10)	0.0047 (10)	−0.0040 (10)
C18	0.0402 (16)	0.0344 (15)	0.0263 (13)	−0.0053 (12)	0.0039 (12)	−0.0008 (12)
C19	0.056 (2)	0.0455 (18)	0.0320 (16)	−0.0122 (15)	0.0005 (14)	−0.0122 (14)
C20	0.0526 (19)	0.0357 (17)	0.0466 (18)	−0.0199 (15)	0.0068 (15)	−0.0145 (14)
C21	0.0488 (18)	0.0270 (15)	0.0405 (16)	−0.0090 (13)	0.0107 (13)	−0.0018 (12)
C22	0.0351 (15)	0.0269 (14)	0.0272 (13)	−0.0018 (11)	0.0025 (11)	−0.0022 (11)
C23	0.0311 (15)	0.0308 (15)	0.0346 (15)	0.0120 (11)	0.0121 (12)	0.0054 (12)
C24	0.0333 (17)	0.059 (2)	0.0442 (19)	0.0145 (15)	0.0171 (14)	0.0121 (16)

Ru1—C6	2.180 (2)	C9—H9C	0.98 (4)
Ru1—C5	2.201 (2)	C10—H10A	0.95 (4)
Ru1—C1	2.213 (2)	C10—H10B	0.95 (4)
Ru1—C2	2.228 (3)	C10—H10C	1.03 (3)
Ru1—C4	2.237 (2)	C11—C12	1.393 (3)
Ru1—C3	2.242 (2)	C11—C16	1.397 (3)
Ru1—P1	2.3147 (6)	C12—C13	1.386 (4)
Ru1—Cl2	2.3992 (6)	C12—H12	0.98 (3)
Ru1—Cl1	2.4124 (6)	C13—C14	1.377 (4)
P1—O1	1.6187 (17)	C13—H13	0.97 (3)
P1—C11	1.805 (2)	C14—C15	1.383 (4)
P1—C17	1.829 (2)	C14—H14	0.92 (3)
O1—C23	1.451 (3)	C15—C16	1.375 (4)
C1—C6	1.401 (4)	C15—H15	0.95 (3)
C1—C2	1.426 (4)	C16—H16	0.87 (3)
C1—C7	1.502 (4)	C17—C22	1.382 (3)
C2—C3	1.382 (4)	C17—C18	1.398 (3)
C2—H2	0.88 (3)	C18—C19	1.383 (4)
C3—C4	1.430 (4)	C18—H18	0.91 (3)
C3—H3	0.91 (2)	C19—C20	1.386 (4)
C4—C5	1.404 (3)	C19—H19	0.93 (3)
C4—C8	1.519 (4)	C20—C21	1.373 (4)
C5—C6	1.422 (4)	C20—H20	0.86 (3)
C5—H5	0.92 (3)	C21—C22	1.391 (4)
C6—H6	0.91 (2)	C21—H21	0.93 (3)
C7—H7A	0.94 (4)	C22—H22	0.94 (2)
C7—H7B	0.98 (4)	C23—C24	1.497 (4)
C7—H7C	0.91 (3)	C23—H23A	0.94 (3)
C8—C10	1.497 (5)	C23—H23B	1.00 (3)
C8—C9	1.530 (4)	C24—H24A	0.98 (3)
C8—H8	0.96 (3)	C24—H24B	0.98 (4)
C9—H9A	0.95 (4)	C24—H24C	0.94 (3)
C9—H9B	1.06 (4)
C6—Ru1—C5	37.88 (10)	C1—C6—H6	120.1 (16)
C6—Ru1—C1	37.18 (10)	C5—C6—H6	118.3 (16)
C5—Ru1—C1	67.83 (10)	Ru1—C6—H6	124.3 (16)
C6—Ru1—C2	66.27 (10)	C1—C7—H7A	110 (2)
C5—Ru1—C2	78.12 (10)	C1—C7—H7B	121 (3)
C1—Ru1—C2	37.45 (10)	H7A—C7—H7B	109 (3)
C6—Ru1—C4	67.57 (9)	C1—C7—H7C	108 (2)
C5—Ru1—C4	36.88 (9)	H7A—C7—H7C	106 (3)
C1—Ru1—C4	80.35 (9)	H7B—C7—H7C	102 (3)
C2—Ru1—C4	66.31 (10)	C10—C8—C4	114.5 (3)
C6—Ru1—C3	78.61 (10)	C10—C8—C9	111.5 (3)
C5—Ru1—C3	66.28 (10)	C4—C8—C9	109.5 (3)
C1—Ru1—C3	67.02 (10)	C10—C8—H8	109.3 (19)
C2—Ru1—C3	36.02 (10)	C4—C8—H8	106.9 (19)
C4—Ru1—C3	37.24 (10)	C9—C8—H8	104.6 (19)
C6—Ru1—P1	92.19 (7)	C8—C9—H9A	117 (3)
C5—Ru1—P1	93.92 (7)	C8—C9—H9B	109 (2)
C1—Ru1—P1	116.63 (7)	H9A—C9—H9B	106 (3)
C2—Ru1—P1	154.01 (8)	C8—C9—H9C	106 (2)
C4—Ru1—P1	120.35 (7)	H9A—C9—H9C	110 (3)
C3—Ru1—P1	157.59 (8)	H9B—C9—H9C	108 (3)
C6—Ru1—Cl2	150.41 (8)	C8—C10—H10A	112 (2)
C5—Ru1—Cl2	112.84 (7)	C8—C10—H10B	115 (3)
C1—Ru1—Cl2	158.61 (7)	H10A—C10—H10B	112 (3)
C2—Ru1—Cl2	121.18 (8)	C8—C10—H10C	106.6 (17)
C4—Ru1—Cl2	88.65 (6)	H10A—C10—H10C	106 (3)
C3—Ru1—Cl2	93.21 (7)	H10B—C10—H10C	104 (3)
P1—Ru1—Cl2	84.75 (2)	C12—C11—C16	118.7 (2)
C6—Ru1—Cl1	119.46 (7)	C12—C11—P1	120.77 (18)
C5—Ru1—Cl1	156.97 (7)	C16—C11—P1	120.46 (19)
C1—Ru1—Cl1	89.97 (7)	C13—C12—C11	120.4 (3)
C2—Ru1—Cl1	87.95 (8)	C13—C12—H12	120.1 (16)
C4—Ru1—Cl1	148.65 (7)	C11—C12—H12	119.5 (16)
C3—Ru1—Cl1	111.67 (8)	C14—C13—C12	120.0 (3)
P1—Ru1—Cl1	90.67 (2)	C14—C13—H13	120.1 (15)
Cl2—Ru1—Cl1	90.04 (2)	C12—C13—H13	119.8 (15)
O1—P1—C11	97.57 (10)	C13—C14—C15	120.2 (3)
O1—P1—C17	103.62 (10)	C13—C14—H14	119.6 (18)
C11—P1—C17	102.15 (11)	C15—C14—H14	120.2 (18)
O1—P1—Ru1	114.92 (7)	C16—C15—C14	120.1 (3)
C11—P1—Ru1	111.87 (8)	C16—C15—H15	121.0 (17)
C17—P1—Ru1	123.10 (8)	C14—C15—H15	118.8 (17)
C23—O1—P1	119.18 (15)	C15—C16—C11	120.6 (3)
C6—C1—C2	117.0 (2)	C15—C16—H16	123.9 (18)
C6—C1—C7	121.6 (3)	C11—C16—H16	115.5 (18)
C2—C1—C7	121.4 (3)	C22—C17—C18	119.6 (2)
C6—C1—Ru1	70.10 (14)	C22—C17—P1	123.84 (18)
C2—C1—Ru1	71.82 (15)	C18—C17—P1	116.54 (19)
C7—C1—Ru1	130.0 (2)	C19—C18—C17	120.3 (3)
C3—C2—C1	122.3 (3)	C19—C18—H18	116.4 (17)
C3—C2—Ru1	72.54 (15)	C17—C18—H18	123.2 (17)
C1—C2—Ru1	70.73 (15)	C18—C19—C20	119.5 (3)
C3—C2—H2	122.3 (19)	C18—C19—H19	119.9 (19)
C1—C2—H2	114.8 (19)	C20—C19—H19	120.6 (19)
Ru1—C2—H2	123.0 (17)	C21—C20—C19	120.4 (3)
C2—C3—C4	120.5 (2)	C21—C20—H20	120.2 (19)
C2—C3—Ru1	71.44 (15)	C19—C20—H20	119.2 (19)
C4—C3—Ru1	71.21 (14)	C20—C21—C22	120.4 (3)
C2—C3—H3	119.4 (16)	C20—C21—H21	119.5 (19)
C4—C3—H3	119.8 (16)	C22—C21—H21	120.1 (19)
Ru1—C3—H3	125.2 (16)	C17—C22—C21	119.7 (2)
C5—C4—C3	118.0 (2)	C17—C22—H22	121.4 (15)
C5—C4—C8	123.3 (3)	C21—C22—H22	118.8 (15)
C3—C4—C8	118.7 (2)	O1—C23—C24	107.2 (2)
C5—C4—Ru1	70.18 (14)	O1—C23—H23A	105.7 (18)
C3—C4—Ru1	71.56 (14)	C24—C23—H23A	111.1 (18)
C8—C4—Ru1	130.35 (17)	O1—C23—H23B	109.4 (15)
C4—C5—C6	120.7 (2)	C24—C23—H23B	110.2 (15)
C4—C5—Ru1	72.94 (14)	H23A—C23—H23B	113 (2)
C6—C5—Ru1	70.22 (14)	C23—C24—H24A	109.7 (19)
C4—C5—H5	120.3 (16)	C23—C24—H24B	113 (2)
C6—C5—H5	118.6 (16)	H24A—C24—H24B	113 (3)
Ru1—C5—H5	123.4 (17)	C23—C24—H24C	107 (2)
C1—C6—C5	121.5 (2)	H24A—C24—H24C	105 (3)
C1—C6—Ru1	72.72 (15)	H24B—C24—H24C	109 (3)
C5—C6—Ru1	71.89 (14)
C6—Ru1—P1—O1	−35.73 (10)	P1—Ru1—C4—C5	49.58 (16)
C5—Ru1—P1—O1	−73.63 (9)	Cl2—Ru1—C4—C5	132.70 (15)
C1—Ru1—P1—O1	−6.51 (10)	Cl1—Ru1—C4—C5	−139.44 (14)
C2—Ru1—P1—O1	−2.91 (19)	C6—Ru1—C4—C3	100.96 (17)
C4—Ru1—P1—O1	−100.89 (10)	C5—Ru1—C4—C3	130.2 (2)
C3—Ru1—P1—O1	−100.5 (2)	C1—Ru1—C4—C3	64.48 (16)
Cl2—Ru1—P1—O1	173.77 (7)	C2—Ru1—C4—C3	28.07 (15)
Cl1—Ru1—P1—O1	83.79 (7)	P1—Ru1—C4—C3	179.78 (13)
C6—Ru1—P1—C11	74.33 (11)	Cl2—Ru1—C4—C3	−97.10 (14)
C5—Ru1—P1—C11	36.43 (11)	Cl1—Ru1—C4—C3	−9.2 (2)
C1—Ru1—P1—C11	103.55 (12)	C6—Ru1—C4—C8	−146.6 (3)
C2—Ru1—P1—C11	107.15 (19)	C5—Ru1—C4—C8	−117.4 (3)
C4—Ru1—P1—C11	9.17 (11)	C1—Ru1—C4—C8	176.9 (3)
C3—Ru1—P1—C11	9.5 (2)	C2—Ru1—C4—C8	140.5 (3)
Cl2—Ru1—P1—C11	−76.17 (9)	C3—Ru1—C4—C8	112.4 (3)
Cl1—Ru1—P1—C11	−166.15 (9)	P1—Ru1—C4—C8	−67.8 (3)
C6—Ru1—P1—C17	−163.51 (12)	Cl2—Ru1—C4—C8	15.3 (2)
C5—Ru1—P1—C17	158.59 (11)	Cl1—Ru1—C4—C8	103.2 (3)
C1—Ru1—P1—C17	−134.29 (12)	C3—C4—C5—C6	−1.5 (3)
C2—Ru1—P1—C17	−130.70 (19)	C8—C4—C5—C6	179.5 (2)
C4—Ru1—P1—C17	131.33 (11)	Ru1—C4—C5—C6	53.6 (2)
C3—Ru1—P1—C17	131.7 (2)	C3—C4—C5—Ru1	−55.1 (2)
Cl2—Ru1—P1—C17	45.98 (9)	C8—C4—C5—Ru1	125.9 (2)
Cl1—Ru1—P1—C17	−43.99 (9)	C6—Ru1—C5—C4	132.7 (2)
C11—P1—O1—C23	176.00 (19)	C1—Ru1—C5—C4	103.97 (17)
C17—P1—O1—C23	71.5 (2)	C2—Ru1—C5—C4	66.18 (16)
Ru1—P1—O1—C23	−65.57 (19)	C3—Ru1—C5—C4	30.32 (15)
C5—Ru1—C1—C6	29.19 (15)	P1—Ru1—C5—C4	−138.82 (14)
C2—Ru1—C1—C6	128.8 (2)	Cl2—Ru1—C5—C4	−52.87 (16)
C4—Ru1—C1—C6	65.40 (16)	Cl1—Ru1—C5—C4	120.15 (18)
C3—Ru1—C1—C6	101.78 (17)	C1—Ru1—C5—C6	−28.68 (15)
P1—Ru1—C1—C6	−53.82 (16)	C2—Ru1—C5—C6	−66.47 (16)
Cl2—Ru1—C1—C6	125.43 (19)	C4—Ru1—C5—C6	−132.7 (2)
Cl1—Ru1—C1—C6	−144.56 (15)	C3—Ru1—C5—C6	−102.33 (17)
C6—Ru1—C1—C2	−128.8 (2)	P1—Ru1—C5—C6	88.53 (14)
C5—Ru1—C1—C2	−99.58 (17)	Cl2—Ru1—C5—C6	174.48 (13)
C4—Ru1—C1—C2	−63.37 (17)	Cl1—Ru1—C5—C6	−12.5 (3)
C3—Ru1—C1—C2	−26.99 (16)	C2—C1—C6—C5	1.1 (4)
P1—Ru1—C1—C2	177.41 (14)	C7—C1—C6—C5	179.5 (3)
Cl2—Ru1—C1—C2	−3.3 (3)	Ru1—C1—C6—C5	−55.1 (2)
Cl1—Ru1—C1—C2	86.67 (16)	C2—C1—C6—Ru1	56.2 (2)
C6—Ru1—C1—C7	115.1 (4)	C7—C1—C6—Ru1	−125.4 (3)
C5—Ru1—C1—C7	144.3 (3)	C4—C5—C6—C1	0.6 (4)
C2—Ru1—C1—C7	−116.1 (4)	Ru1—C5—C6—C1	55.5 (2)
C4—Ru1—C1—C7	−179.5 (3)	C4—C5—C6—Ru1	−54.8 (2)
C3—Ru1—C1—C7	−143.1 (3)	C5—Ru1—C6—C1	−132.7 (2)
P1—Ru1—C1—C7	61.3 (3)	C2—Ru1—C6—C1	−31.19 (16)
Cl2—Ru1—C1—C7	−119.4 (3)	C4—Ru1—C6—C1	−104.13 (17)
Cl1—Ru1—C1—C7	−29.4 (3)	C3—Ru1—C6—C1	−66.83 (16)
C6—C1—C2—C3	−2.0 (4)	P1—Ru1—C6—C1	133.78 (15)
C7—C1—C2—C3	179.6 (3)	Cl2—Ru1—C6—C1	−143.00 (14)
Ru1—C1—C2—C3	53.3 (2)	Cl1—Ru1—C6—C1	41.76 (17)
C6—C1—C2—Ru1	−55.3 (2)	C1—Ru1—C6—C5	132.7 (2)
C7—C1—C2—Ru1	126.3 (3)	C2—Ru1—C6—C5	101.47 (17)
C6—Ru1—C2—C3	−103.75 (19)	C4—Ru1—C6—C5	28.53 (15)
C5—Ru1—C2—C3	−65.80 (17)	C3—Ru1—C6—C5	65.83 (16)
C1—Ru1—C2—C3	−134.7 (3)	P1—Ru1—C6—C5	−93.57 (14)
C4—Ru1—C2—C3	−28.96 (16)	Cl2—Ru1—C6—C5	−10.3 (2)
P1—Ru1—C2—C3	−140.02 (16)	Cl1—Ru1—C6—C5	174.42 (12)
Cl2—Ru1—C2—C3	43.85 (19)	C5—C4—C8—C10	−9.4 (4)
Cl1—Ru1—C2—C3	132.65 (16)	C3—C4—C8—C10	171.6 (3)
C6—Ru1—C2—C1	30.98 (16)	Ru1—C4—C8—C10	82.1 (4)
C5—Ru1—C2—C1	68.93 (16)	C5—C4—C8—C9	116.6 (3)
C4—Ru1—C2—C1	105.77 (18)	C3—C4—C8—C9	−62.3 (4)
C3—Ru1—C2—C1	134.7 (3)	Ru1—C4—C8—C9	−151.9 (3)
P1—Ru1—C2—C1	−5.3 (3)	O1—P1—C11—C12	27.2 (2)
Cl2—Ru1—C2—C1	178.57 (13)	C17—P1—C11—C12	132.9 (2)
Cl1—Ru1—C2—C1	−92.62 (15)	Ru1—P1—C11—C12	−93.6 (2)
C1—C2—C3—C4	1.1 (4)	O1—P1—C11—C16	−155.1 (2)
Ru1—C2—C3—C4	53.6 (2)	C17—P1—C11—C16	−49.3 (2)
C1—C2—C3—Ru1	−52.5 (2)	Ru1—P1—C11—C16	84.2 (2)
C6—Ru1—C3—C2	65.11 (18)	C16—C11—C12—C13	−0.7 (4)
C5—Ru1—C3—C2	102.84 (18)	P1—C11—C12—C13	177.0 (2)
C1—Ru1—C3—C2	27.99 (17)	C11—C12—C13—C14	0.6 (4)
C4—Ru1—C3—C2	132.9 (2)	C12—C13—C14—C15	−0.2 (5)
P1—Ru1—C3—C2	132.40 (19)	C13—C14—C15—C16	−0.1 (5)
Cl2—Ru1—C3—C2	−143.59 (16)	C14—C15—C16—C11	−0.1 (4)
Cl1—Ru1—C3—C2	−52.27 (18)	C12—C11—C16—C15	0.5 (4)
C6—Ru1—C3—C4	−67.78 (15)	P1—C11—C16—C15	−177.3 (2)
C5—Ru1—C3—C4	−30.05 (14)	O1—P1—C17—C22	−128.6 (2)
C1—Ru1—C3—C4	−104.90 (17)	C11—P1—C17—C22	130.4 (2)
C2—Ru1—C3—C4	−132.9 (2)	Ru1—P1—C17—C22	3.9 (2)
P1—Ru1—C3—C4	−0.5 (3)	O1—P1—C17—C18	53.3 (2)
Cl2—Ru1—C3—C4	83.53 (14)	C11—P1—C17—C18	−47.7 (2)
Cl1—Ru1—C3—C4	174.85 (12)	Ru1—P1—C17—C18	−174.27 (16)
C2—C3—C4—C5	0.7 (4)	C22—C17—C18—C19	−1.5 (4)
Ru1—C3—C4—C5	54.4 (2)	P1—C17—C18—C19	176.7 (2)
C2—C3—C4—C8	179.7 (2)	C17—C18—C19—C20	1.0 (5)
Ru1—C3—C4—C8	−126.5 (2)	C18—C19—C20—C21	0.3 (5)
C2—C3—C4—Ru1	−53.8 (2)	C19—C20—C21—C22	−1.1 (5)
C6—Ru1—C4—C5	−29.25 (15)	C18—C17—C22—C21	0.8 (4)
C1—Ru1—C4—C5	−65.72 (16)	P1—C17—C22—C21	−177.3 (2)
C2—Ru1—C4—C5	−102.14 (17)	C20—C21—C22—C17	0.5 (4)
C3—Ru1—C4—C5	−130.2 (2)	P1—O1—C23—C24	163.4 (2)

	Title compound	[Ru(η6-p-cymene)Cl2PPhOEt2]a	[Ru(η6-p-cymene)Cl2PPh3]b
Ru—P	2.3147 (6)	2.2807 (7)	2.3438 (6)
Ru—Cl1	2.4124 (6)	2.4171 (7)	2.4154 (6)
Ru—Cl2	2.3992 (6)	2.4038 (7)	2.4151 (6)
Ru—C(av)	2.217 (1)	2.218 (4)	2.218 (2)
P—Ru – Cl1	90.67 (2)	87.59 (2)	87.094 (19)
P—Ru – Cl2	84.75 (2)	87.89 (2)	90.27 (2)
Cl1—Ru – Cl2	90.04 (2)	88.81 (2)	88.41 (2)
Σ angles	265.46	264.29	265.77

Table 1

Selected geometric parameters (Å, °) for the title compound and related compounds

Σ angles = sum of P—Ru—Cl1, P—Ru—Cl2, and Cl1—Ru— Cl2 angles.

	Title compound	[Ru(η6-p-cymene)Cl2PPhOEt2]a	[Ru(η6-p-cymene)Cl2PPh3]b
Ru—P	2.3147 (6)	2.2807 (7)	2.3438 (6)
Ru—Cl1	2.4124 (6)	2.4171 (7)	2.4154 (6)
Ru—Cl2	2.3992 (6)	2.4038 (7)	2.4151 (6)
Ru—C(av)	2.217 (1)	2.218 (4)	2.218 (2)
P—Ru – Cl1	90.67 (2)	87.59 (2)	87.094 (19)
P—Ru – Cl2	84.75 (2)	87.89 (2)	90.27 (2)
Cl1—Ru – Cl2	90.04 (2)	88.81 (2)	88.41 (2)
Σ angles	265.46	264.29	265.77

Notes: (a) Albertin et al. (2010 ▶); (b) Elsegood et al. (2006 ▶).