trans-Dichlorido(2,2-dimethyl-propane-1,3-diamine)-bis-(triphenyl-phosphane)ruthenium(II).

In the title compound, [RuCl(2)(C(5)H(14)N(2))(C(18)H(15)P)(2)], the Ru(II) atom is six-coordinated, forming a slightly distorted octa-hedral geometry, with two chloride ions in an axial arrangement, and two P atoms of two triphenyl-phosphane and two chelating N atoms of the bidentate 2,2-dimethyl-propane-1,3-diamine ligand located in the equatorial plane. The average Ru-P, Ru-N and Ru-Cl bond lengths are 2.325 (18), 2.1845 (7) and 2.4123 (12) Å, respectively.

Related literature

For the reduction of pan> class="Chemical">ketones to secondary alcohols, see: Noyori (1994 ▶). For enanti­oselective hydrogenation of prochiral carbonyl compounds to chiral alcohols, see: Drozdzak et al. (2005 ▶). For background to stereo-, regio- and enantio-selective ruthenium catalysis, see: Clarke (2002 ▶); Noyori (2003 ▶) and references therein. For RuII catalysts, see: Noyori & Ohkuma (2001 ▶); Ohkuma et al. (2002 ▶); Lindner et al. (2005 ▶). For related structures, see: Nachtigall et al. (2002 ▶); Lindner et al. (2003a ▶,b ▶); Doucet et al. (1998 ▶); Warad et al. (2006 ▶).

Experimental

Crystal data

[n class="Chemical">Rupan> class="Chemical">Cl2(C5H14N2)(C18H15P)2]

M = 798.69

Monon class="Chemical">clinpan>ipan> class="Chemical">c,

a = 17.393 (2) Å

b = 10.3493 (16) Å

n class="Chemical">c = 21.315 (2) Å

β = 102.181 (15)°

V = 3750.4 (9) Å3

Z = 4

Mo Kα radiation

μ = 0.68 mm−1

T = 293 K

0.60 × 0.60 × 0.05 mm

Data collection

Enraf–n class="Chemical">Nonpan>ius pan> class="Chemical">CAD-4 diffractometer

Absorption n class="Chemical">correpan> class="Chemical">ction: ψ scan (North et al., 1968 ▶) T min = 0.687, T max = 0.967

7922 measured reflen class="Chemical">ctions

7319 independent reflen class="Chemical">ctionpan>s

5387 reflen class="Chemical">ctions with I > 2σ(I)

R int = 0.025

3 standard reflen class="Chemical">ctionpan>s every 400 reflepan> class="Chemical">ctions intensity decay: 2%

Refinement

R[F 2 > 2σ(F 2)] = 0.034

wR(F 2) = 0.078

S = 1.03

7319 reflen class="Chemical">ctions

436 parameters

Only H-atom n class="Chemical">coordinates refined

Δρmax = 0.39 e Å−3

Δρmin = −0.51 e Å−3

Data collepan> class="Chemical">ction: CAD-4 EXPRESS (Enraf–Nonius, 1994 ▶); cell refinement: CAD-4 EXPRESS; data reduction: HELENA (Spek, 1996 ▶); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: PLATON (Spek, 2009 ▶); software used to prepare material for publication: XCIF in SHELXTL (Sheldrick, 2008 ▶).

n class="Chemical">Crystal stpan> class="Chemical">ructure: contains datablocks global, I. DOI: 10.1107/S1600536810019276/tk2679sup1.cif

Stn class="Chemical">rupan> class="Chemical">cture factors: contains datablocks I. DOI: 10.1107/S1600536810019276/tk2679Isup2.hkl

Additional supplementary materials: n class="Chemical">crystallographipan> class="Chemical">c information; 3D view; checkCIF report

[RuCl2(C5H14N2)(C18H15P)2]	F(000) = 1648
Mr = 798.69	Dx = 1.411 Mg m−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.70930 Å
Hall symbol: -P 2ybc	Cell parameters from 25 reflections
a = 17.393 (2) Å	θ = 7.8–12.3°
b = 10.3493 (16) Å	µ = 0.68 mm−1
c = 21.315 (2) Å	T = 293 K
β = 102.181 (15)°	Plate, brown
V = 3750.4 (9) Å3	0.60 × 0.60 × 0.05 mm
Z = 4

Enraf–Nonius CAD-4 diffractometer	5387 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	Rint = 0.025
graphite	θmax = 25.9°, θmin = 3.1°
ω scans	h = −21→21
Absorption correction: ψ scan (North et al., 1968)	k = 0→12
Tmin = 0.687, Tmax = 0.967	l = −1→26
7922 measured reflections	3 standard reflections every 400 reflections
7319 independent reflections	intensity decay: 2%

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)] = 0.034	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.078	Only H-atom coordinates refined
S = 1.03	w = 1/[σ2(Fo2) + (0.027P)2 + 1.9538P] where P = (Fo2 + 2Fc2)/3
7319 reflections	(Δ/σ)max = 0.001
436 parameters	Δρmax = 0.39 e Å−3
0 restraints	Δρmin = −0.51 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	0.293247 (13)	0.49329 (2)	0.344643 (10)	0.02586 (7)
Cl1	0.39278 (5)	0.65793 (8)	0.37293 (4)	0.0421 (2)
Cl2	0.22021 (5)	0.29446 (7)	0.32284 (4)	0.0424 (2)
P1	0.19157 (4)	0.59121 (7)	0.38125 (4)	0.02806 (17)
C111	0.09258 (16)	0.5977 (3)	0.32882 (14)	0.0316 (7)
C112	0.07724 (19)	0.6794 (3)	0.27611 (15)	0.0386 (7)
H11A	0.1169	0.7326	0.2675	0.046*
C113	0.0032 (2)	0.6825 (3)	0.23610 (17)	0.0494 (9)
H11B	−0.0067	0.7391	0.2014	0.059*
C114	−0.0553 (2)	0.6028 (4)	0.24725 (18)	0.0520 (10)
H11C	−0.1048	0.6050	0.2202	0.062*
C115	−0.04061 (19)	0.5199 (4)	0.29828 (18)	0.0508 (9)
H11D	−0.0801	0.4647	0.3054	0.061*
C116	0.03250 (18)	0.5174 (3)	0.33944 (16)	0.0417 (8)
H11E	0.0415	0.4616	0.3744	0.050*
C121	0.20843 (17)	0.7563 (3)	0.41445 (14)	0.0315 (7)
C122	0.2748 (2)	0.7740 (3)	0.46276 (16)	0.0452 (8)
H12A	0.3091	0.7052	0.4751	0.054*
C123	0.2907 (2)	0.8923 (4)	0.49275 (19)	0.0559 (10)
H12B	0.3345	0.9016	0.5261	0.067*
C124	0.2429 (2)	0.9950 (4)	0.47395 (19)	0.0562 (10)
H12C	0.2542	1.0745	0.4942	0.067*
C125	0.1782 (2)	0.9815 (3)	0.42524 (19)	0.0547 (10)
H12D	0.1461	1.0523	0.4116	0.066*
C126	0.1605 (2)	0.8617 (3)	0.39623 (16)	0.0430 (8)
H12E	0.1156	0.8526	0.3640	0.052*
C131	0.16632 (17)	0.5131 (3)	0.45301 (14)	0.0350 (7)
C132	0.1386 (2)	0.5845 (4)	0.49815 (18)	0.0578 (10)
H13A	0.1363	0.6740	0.4942	0.069*
C133	0.1142 (3)	0.5270 (4)	0.5490 (2)	0.0828 (16)
H13B	0.0953	0.5775	0.5785	0.099*
C134	0.1179 (3)	0.3955 (4)	0.5561 (2)	0.0754 (14)
H13C	0.1028	0.3568	0.5909	0.090*
C135	0.1439 (2)	0.3217 (4)	0.5118 (2)	0.0647 (11)
H13D	0.1453	0.2322	0.5159	0.078*
C136	0.1682 (2)	0.3799 (3)	0.46079 (17)	0.0485 (9)
H13E	0.1861	0.3286	0.4311	0.058*
P2	0.26561 (4)	0.57378 (7)	0.23985 (4)	0.02910 (17)
C211	0.17237 (18)	0.5472 (3)	0.18165 (14)	0.0337 (7)
C212	0.1466 (2)	0.6279 (4)	0.12963 (17)	0.0577 (10)
H21A	0.1754	0.7014	0.1246	0.069*
C213	0.0781 (3)	0.6003 (5)	0.08490 (18)	0.0713 (13)
H21B	0.0607	0.6563	0.0507	0.086*
C214	0.0359 (2)	0.4905 (4)	0.09095 (17)	0.0631 (11)
H21C	−0.0092	0.4708	0.0603	0.076*
C215	0.0604 (2)	0.4106 (4)	0.14206 (17)	0.0536 (10)
H21D	0.0321	0.3360	0.1463	0.064*
C216	0.1271 (2)	0.4399 (3)	0.18753 (16)	0.0449 (8)
H21E	0.1419	0.3862	0.2230	0.054*
C221	0.28413 (18)	0.7468 (3)	0.22798 (15)	0.0344 (7)
C222	0.26872 (18)	0.8358 (3)	0.27232 (16)	0.0405 (8)
H22A	0.2537	0.8066	0.3092	0.049*
C223	0.2753 (2)	0.9669 (3)	0.2627 (2)	0.0540 (10)
H22B	0.2638	1.0251	0.2927	0.065*
C224	0.2986 (3)	1.0114 (4)	0.2091 (2)	0.0687 (12)
H22C	0.3029	1.0997	0.2025	0.082*
C225	0.3156 (3)	0.9248 (4)	0.1651 (2)	0.0714 (13)
H22D	0.3320	0.9549	0.1290	0.086*
C226	0.3088 (2)	0.7939 (3)	0.17389 (18)	0.0527 (9)
H22E	0.3206	0.7364	0.1437	0.063*
C231	0.33381 (18)	0.4979 (3)	0.19493 (14)	0.0372 (7)
C232	0.4127 (2)	0.5332 (4)	0.20829 (18)	0.0529 (10)
H23A	0.4294	0.6053	0.2336	0.063*
C233	0.4668 (2)	0.4602 (5)	0.1836 (2)	0.0725 (14)
H23B	0.5197	0.4830	0.1930	0.087*
C234	0.4424 (3)	0.3548 (5)	0.1456 (2)	0.0802 (15)
H23C	0.4788	0.3063	0.1293	0.096*
C235	0.3650 (3)	0.3213 (4)	0.1316 (2)	0.0735 (13)
H23D	0.3486	0.2506	0.1052	0.088*
C236	0.3109 (2)	0.3911 (3)	0.15613 (16)	0.0495 (9)
H23E	0.2583	0.3665	0.1466	0.059*
N1	0.38992 (15)	0.3781 (3)	0.32350 (12)	0.0411 (7)
H1N1	0.3780	0.3623	0.2810	0.049*
H2N1	0.4325	0.4298	0.3306	0.049*
N2	0.34248 (15)	0.4290 (3)	0.44251 (12)	0.0383 (6)
H1N2	0.3807	0.4856	0.4590	0.046*
H2N2	0.3043	0.4393	0.4647	0.046*
C1	0.4154 (2)	0.2550 (3)	0.35469 (16)	0.0489 (9)
H1B	0.4582	0.2214	0.3369	0.059*
H1C	0.3722	0.1941	0.3445	0.059*
C2	0.3752 (2)	0.3010 (4)	0.45837 (17)	0.0549 (10)
H2B	0.3332	0.2382	0.4463	0.066*
H2C	0.3934	0.2959	0.5046	0.066*
C3	0.4423 (2)	0.2623 (3)	0.42720 (15)	0.0434 (8)
C4	0.5121 (2)	0.3503 (4)	0.44572 (19)	0.0664 (12)
H4A	0.4975	0.4364	0.4311	0.100*
H4B	0.5539	0.3203	0.4263	0.100*
H4C	0.5296	0.3505	0.4916	0.100*
C5	0.4653 (3)	0.1253 (4)	0.4505 (2)	0.0764 (14)
H5A	0.4828	0.1255	0.4963	0.115*
H5B	0.5070	0.0950	0.4311	0.115*
H5C	0.4206	0.0693	0.4386	0.115*

	U11	U22	U33	U12	U13	U23
Ru1	0.02516 (11)	0.02601 (12)	0.02646 (11)	0.00136 (11)	0.00557 (8)	0.00011 (11)
Cl1	0.0348 (4)	0.0439 (5)	0.0458 (5)	−0.0102 (4)	0.0044 (3)	0.0005 (4)
Cl2	0.0489 (5)	0.0297 (4)	0.0447 (5)	−0.0058 (4)	0.0014 (4)	−0.0002 (3)
P1	0.0275 (4)	0.0273 (4)	0.0300 (4)	0.0013 (3)	0.0073 (3)	−0.0002 (3)
C111	0.0276 (15)	0.0320 (16)	0.0358 (16)	0.0038 (13)	0.0082 (13)	−0.0051 (13)
C112	0.0390 (18)	0.0373 (18)	0.0391 (18)	0.0005 (15)	0.0074 (14)	−0.0027 (15)
C113	0.051 (2)	0.045 (2)	0.046 (2)	0.0098 (18)	−0.0050 (17)	0.0030 (17)
C114	0.0343 (18)	0.058 (2)	0.058 (2)	0.0082 (18)	−0.0039 (17)	−0.014 (2)
C115	0.0355 (17)	0.058 (2)	0.058 (2)	−0.0098 (17)	0.0094 (16)	−0.007 (2)
C116	0.0353 (16)	0.046 (2)	0.0440 (18)	−0.0061 (16)	0.0079 (14)	−0.0025 (16)
C121	0.0353 (16)	0.0287 (15)	0.0336 (17)	0.0016 (13)	0.0144 (13)	−0.0014 (13)
C122	0.0430 (19)	0.0414 (19)	0.049 (2)	0.0038 (16)	0.0040 (16)	−0.0042 (16)
C123	0.050 (2)	0.055 (2)	0.059 (2)	−0.0112 (19)	0.0025 (18)	−0.018 (2)
C124	0.065 (2)	0.0357 (19)	0.071 (3)	−0.011 (2)	0.021 (2)	−0.022 (2)
C125	0.069 (2)	0.0305 (19)	0.066 (2)	0.0093 (18)	0.017 (2)	−0.0052 (18)
C126	0.0421 (19)	0.0397 (19)	0.046 (2)	0.0055 (15)	0.0079 (16)	−0.0052 (16)
C131	0.0325 (15)	0.0392 (18)	0.0349 (15)	−0.0011 (15)	0.0105 (12)	0.0021 (15)
C132	0.087 (3)	0.041 (2)	0.059 (2)	−0.005 (2)	0.044 (2)	−0.0039 (18)
C133	0.137 (4)	0.057 (3)	0.077 (3)	−0.013 (3)	0.076 (3)	−0.008 (2)
C134	0.108 (4)	0.068 (3)	0.064 (3)	−0.005 (3)	0.051 (3)	0.012 (2)
C135	0.081 (3)	0.047 (2)	0.077 (3)	0.006 (2)	0.041 (2)	0.017 (2)
C136	0.060 (2)	0.0385 (19)	0.055 (2)	0.0082 (17)	0.0294 (19)	0.0069 (17)
P2	0.0320 (4)	0.0273 (4)	0.0286 (4)	0.0006 (3)	0.0079 (3)	0.0012 (3)
C211	0.0368 (17)	0.0363 (16)	0.0278 (15)	0.0032 (14)	0.0064 (13)	−0.0006 (13)
C212	0.058 (2)	0.060 (2)	0.047 (2)	−0.013 (2)	−0.0066 (18)	0.0191 (19)
C213	0.076 (3)	0.086 (3)	0.041 (2)	−0.011 (3)	−0.013 (2)	0.025 (2)
C214	0.056 (2)	0.087 (3)	0.040 (2)	−0.015 (2)	−0.0045 (17)	0.001 (2)
C215	0.049 (2)	0.059 (2)	0.050 (2)	−0.0125 (19)	0.0036 (18)	−0.0034 (19)
C216	0.045 (2)	0.048 (2)	0.0402 (19)	−0.0032 (17)	0.0053 (16)	0.0029 (16)
C221	0.0362 (17)	0.0280 (16)	0.0389 (18)	−0.0026 (13)	0.0075 (14)	0.0050 (14)
C222	0.0386 (18)	0.0346 (17)	0.047 (2)	−0.0010 (15)	0.0074 (15)	0.0031 (15)
C223	0.061 (2)	0.0294 (19)	0.071 (3)	−0.0024 (16)	0.012 (2)	−0.0012 (17)
C224	0.088 (3)	0.031 (2)	0.087 (3)	−0.007 (2)	0.020 (3)	0.017 (2)
C225	0.099 (3)	0.049 (2)	0.074 (3)	−0.006 (2)	0.035 (3)	0.023 (2)
C226	0.071 (3)	0.041 (2)	0.050 (2)	0.0000 (19)	0.0215 (19)	0.0081 (17)
C231	0.0444 (17)	0.0372 (16)	0.0345 (16)	0.0093 (17)	0.0184 (13)	0.0109 (16)
C232	0.052 (2)	0.054 (2)	0.058 (2)	0.0082 (18)	0.0243 (18)	0.0162 (18)
C233	0.051 (2)	0.089 (4)	0.089 (3)	0.017 (2)	0.040 (2)	0.039 (3)
C234	0.099 (4)	0.068 (3)	0.092 (4)	0.039 (3)	0.063 (3)	0.022 (3)
C235	0.108 (4)	0.061 (3)	0.064 (3)	0.023 (3)	0.047 (3)	−0.002 (2)
C236	0.068 (2)	0.044 (2)	0.042 (2)	0.0088 (19)	0.0224 (18)	0.0015 (16)
N1	0.0444 (16)	0.0454 (16)	0.0353 (15)	0.0172 (13)	0.0121 (12)	0.0037 (13)
N2	0.0378 (15)	0.0464 (16)	0.0313 (14)	0.0102 (13)	0.0090 (11)	0.0033 (12)
C1	0.058 (2)	0.043 (2)	0.045 (2)	0.0169 (18)	0.0098 (17)	0.0024 (17)
C2	0.071 (3)	0.056 (2)	0.040 (2)	0.023 (2)	0.0158 (18)	0.0165 (18)
C3	0.0454 (19)	0.046 (2)	0.0381 (18)	0.0177 (16)	0.0075 (15)	0.0056 (16)
C4	0.046 (2)	0.087 (3)	0.061 (3)	0.007 (2)	0.0016 (19)	−0.003 (2)
C5	0.102 (4)	0.064 (3)	0.066 (3)	0.039 (3)	0.022 (3)	0.020 (2)

Ru1—N1	2.184 (2)	C213—C214	1.374 (6)
Ru1—N2	2.185 (2)	C213—H21B	0.9300
Ru1—P1	2.3120 (8)	C214—C215	1.362 (5)
Ru1—P2	2.3370 (8)	C214—H21C	0.9300
Ru1—Cl2	2.4114 (8)	C215—C216	1.379 (5)
Ru1—Cl1	2.4131 (8)	C215—H21D	0.9300
P1—C111	1.845 (3)	C216—H21E	0.9300
P1—C121	1.849 (3)	C221—C222	1.385 (4)
P1—C131	1.863 (3)	C221—C226	1.400 (4)
C111—C112	1.387 (4)	C222—C223	1.381 (4)
C111—C116	1.390 (4)	C222—H22A	0.9300
C112—C113	1.386 (4)	C223—C224	1.371 (5)
C112—H11A	0.9300	C223—H22B	0.9300
C113—C114	1.370 (5)	C224—C225	1.374 (6)
C113—H11B	0.9300	C224—H22C	0.9300
C114—C115	1.366 (5)	C225—C226	1.376 (5)
C114—H11C	0.9300	C225—H22D	0.9300
C115—C116	1.384 (4)	C226—H22E	0.9300
C115—H11D	0.9300	C231—C236	1.387 (5)
C116—H11E	0.9300	C231—C232	1.391 (5)
C121—C126	1.377 (4)	C232—C233	1.393 (5)
C121—C122	1.388 (4)	C232—H23A	0.9300
C122—C123	1.382 (5)	C233—C234	1.371 (7)
C122—H12A	0.9300	C233—H23B	0.9300
C123—C124	1.356 (5)	C234—C235	1.361 (7)
C123—H12B	0.9300	C234—H23C	0.9300
C124—C125	1.368 (5)	C235—C236	1.375 (5)
C124—H12C	0.9300	C235—H23D	0.9300
C125—C126	1.391 (5)	C236—H23E	0.9300
C125—H12D	0.9300	N1—C1	1.461 (4)
C126—H12E	0.9300	N1—H1N1	0.9000
C131—C132	1.378 (4)	N1—H2N1	0.9000
C131—C136	1.387 (4)	N2—C2	1.453 (4)
C132—C133	1.380 (5)	N2—H1N2	0.9000
C132—H13A	0.9300	N2—H2N2	0.9000
C133—C134	1.369 (6)	C1—C3	1.520 (4)
C133—H13B	0.9300	C1—H1B	0.9700
C134—C135	1.363 (5)	C1—H1C	0.9700
C134—H13C	0.9300	C2—C3	1.514 (5)
C135—C136	1.386 (5)	C2—H2B	0.9700
C135—H13D	0.9300	C2—H2C	0.9700
C136—H13E	0.9300	C3—C4	1.502 (5)
P2—C211	1.843 (3)	C3—C5	1.527 (5)
P2—C221	1.846 (3)	C4—H4A	0.9600
P2—C231	1.849 (3)	C4—H4B	0.9600
C211—C216	1.383 (4)	C4—H4C	0.9600
C211—C212	1.385 (4)	C5—H5A	0.9600
C212—C213	1.389 (5)	C5—H5B	0.9600
C212—H21A	0.9300	C5—H5C	0.9600
N1—Ru1—N2	82.35 (9)	C212—C213—H21B	119.9
N1—Ru1—P1	170.31 (7)	C215—C214—C213	119.6 (3)
N2—Ru1—P1	89.14 (7)	C215—C214—H21C	120.2
N1—Ru1—P2	90.54 (7)	C213—C214—H21C	120.2
N2—Ru1—P2	168.90 (7)	C214—C215—C216	120.3 (4)
P1—Ru1—P2	98.55 (3)	C214—C215—H21D	119.9
N1—Ru1—Cl2	83.77 (8)	C216—C215—H21D	119.9
N2—Ru1—Cl2	90.48 (8)	C215—C216—C211	121.6 (3)
P1—Ru1—Cl2	91.70 (3)	C215—C216—H21E	119.2
P2—Ru1—Cl2	97.25 (3)	C211—C216—H21E	119.2
N1—Ru1—Cl1	83.92 (8)	C222—C221—C226	117.9 (3)
N2—Ru1—Cl1	81.99 (8)	C222—C221—P2	119.1 (2)
P1—Ru1—Cl1	99.54 (3)	C226—C221—P2	122.9 (3)
P2—Ru1—Cl1	88.81 (3)	C223—C222—C221	121.2 (3)
Cl2—Ru1—Cl1	166.33 (3)	C223—C222—H22A	119.4
C111—P1—C121	104.52 (14)	C221—C222—H22A	119.4
C111—P1—C131	99.29 (13)	C224—C223—C222	120.2 (4)
C121—P1—C131	97.63 (14)	C224—C223—H22B	119.9
C111—P1—Ru1	119.59 (9)	C222—C223—H22B	119.9
C121—P1—Ru1	117.61 (10)	C223—C224—C225	119.6 (4)
C131—P1—Ru1	114.61 (10)	C223—C224—H22C	120.2
C112—C111—C116	118.3 (3)	C225—C224—H22C	120.2
C112—C111—P1	120.5 (2)	C224—C225—C226	120.8 (4)
C116—C111—P1	121.1 (2)	C224—C225—H22D	119.6
C113—C112—C111	120.5 (3)	C226—C225—H22D	119.6
C113—C112—H11A	119.8	C225—C226—C221	120.3 (4)
C111—C112—H11A	119.8	C225—C226—H22E	119.8
C114—C113—C112	120.5 (3)	C221—C226—H22E	119.8
C114—C113—H11B	119.8	C236—C231—C232	118.6 (3)
C112—C113—H11B	119.8	C236—C231—P2	120.8 (3)
C115—C114—C113	119.7 (3)	C232—C231—P2	119.7 (3)
C115—C114—H11C	120.1	C231—C232—C233	119.7 (4)
C113—C114—H11C	120.1	C231—C232—H23A	120.1
C114—C115—C116	120.6 (3)	C233—C232—H23A	120.1
C114—C115—H11D	119.7	C234—C233—C232	120.3 (4)
C116—C115—H11D	119.7	C234—C233—H23B	119.8
C115—C116—C111	120.5 (3)	C232—C233—H23B	119.8
C115—C116—H11E	119.8	C235—C234—C233	120.1 (4)
C111—C116—H11E	119.8	C235—C234—H23C	120.0
C126—C121—C122	117.7 (3)	C233—C234—H23C	120.0
C126—C121—P1	125.9 (2)	C234—C235—C236	120.5 (4)
C122—C121—P1	116.5 (2)	C234—C235—H23D	119.7
C123—C122—C121	120.9 (3)	C236—C235—H23D	119.7
C123—C122—H12A	119.6	C235—C236—C231	120.8 (4)
C121—C122—H12A	119.6	C235—C236—H23E	119.6
C124—C123—C122	120.5 (3)	C231—C236—H23E	119.6
C124—C123—H12B	119.8	C1—N1—Ru1	123.7 (2)
C122—C123—H12B	119.8	C1—N1—H1N1	106.4
C123—C124—C125	120.0 (3)	Ru1—N1—H1N1	106.4
C123—C124—H12C	120.0	C1—N1—H2N1	106.4
C125—C124—H12C	120.0	Ru1—N1—H2N1	106.4
C124—C125—C126	119.8 (3)	H1N1—N1—H2N1	106.5
C124—C125—H12D	120.1	C2—N2—Ru1	123.7 (2)
C126—C125—H12D	120.1	C2—N2—H1N2	106.4
C121—C126—C125	121.1 (3)	Ru1—N2—H1N2	106.4
C121—C126—H12E	119.4	C2—N2—H2N2	106.4
C125—C126—H12E	119.4	Ru1—N2—H2N2	106.4
C132—C131—C136	116.9 (3)	H1N2—N2—H2N2	106.5
C132—C131—P1	121.2 (3)	N1—C1—C3	114.7 (3)
C136—C131—P1	121.7 (2)	N1—C1—H1B	108.6
C131—C132—C133	121.8 (4)	C3—C1—H1B	108.6
C131—C132—H13A	119.1	N1—C1—H1C	108.6
C133—C132—H13A	119.1	C3—C1—H1C	108.6
C134—C133—C132	120.0 (4)	H1B—C1—H1C	107.6
C134—C133—H13B	120.0	N2—C2—C3	116.1 (3)
C132—C133—H13B	120.0	N2—C2—H2B	108.3
C135—C134—C133	119.7 (4)	C3—C2—H2B	108.3
C135—C134—H13C	120.1	N2—C2—H2C	108.3
C133—C134—H13C	120.1	C3—C2—H2C	108.3
C134—C135—C136	120.0 (4)	H2B—C2—H2C	107.4
C134—C135—H13D	120.0	C4—C3—C2	112.3 (3)
C136—C135—H13D	120.0	C4—C3—C1	110.9 (3)
C135—C136—C131	121.5 (3)	C2—C3—C1	111.0 (3)
C135—C136—H13E	119.2	C4—C3—C5	109.6 (3)
C131—C136—H13E	119.2	C2—C3—C5	106.1 (3)
C211—P2—C221	101.92 (14)	C1—C3—C5	106.7 (3)
C211—P2—C231	99.08 (14)	C3—C4—H4A	109.5
C221—P2—C231	101.03 (14)	C3—C4—H4B	109.5
C211—P2—Ru1	124.38 (10)	H4A—C4—H4B	109.5
C221—P2—Ru1	118.04 (10)	C3—C4—H4C	109.5
C231—P2—Ru1	108.57 (10)	H4A—C4—H4C	109.5
C216—C211—C212	117.5 (3)	H4B—C4—H4C	109.5
C216—C211—P2	119.7 (2)	C3—C5—H5A	109.5
C212—C211—P2	122.7 (3)	C3—C5—H5B	109.5
C211—C212—C213	120.8 (4)	H5A—C5—H5B	109.5
C211—C212—H21A	119.6	C3—C5—H5C	109.5
C213—C212—H21A	119.6	H5A—C5—H5C	109.5
C214—C213—C212	120.3 (4)	H5B—C5—H5C	109.5
C214—C213—H21B	119.9