(OC-6-13)-Bis[5-bromo-2-(4-bromo­phenyl­diazenyl)phen­yl]dicarbonyl­ruthenium(II) with mutually trans N-donor atoms

The title compound, [Ru(C₁₂H₇Br₂N₂)₂(CO)₂], possesses a distorted octa­hedral environment about the Ru atom, with two cyclo­metallated 4,4'-dibromo­azobenzene ligands and two mutually cis carbonyl ligands. The donor atoms are arranged such that the N atoms are mutually trans and the aryl C atoms are trans to carbonyl ligands.

Key indicators

• Single-crystal X-ray study
• T = 200 K
• Mean [sigma](C-C) = 0.005 Å
• R factor = 0.024
• wR factor = 0.028
• Data-to-parameter ratio = 12.6

checkCIF/PLATON results

No syntax errors found



Alert level B
PLAT431_ALERT_2_B Short Inter HL..A Contact  Br12   ..  N12     ..       3.09 Ang.

Alert level C
PLAT232_ALERT_2_C Hirshfeld Test Diff (M-X)  Ru1    -   C1      ..       6.37 su
PLAT232_ALERT_2_C Hirshfeld Test Diff (M-X)  Ru1    -   C2      ..       5.88 su
PLAT720_ALERT_4_C Number of Unusual/Non-Standard Label(s) ........         14

Alert level G

   0 ALERT level A = In general: serious problem
   1 ALERT level B = Potentially serious problem
   3 ALERT level C = Check and explain
   1 ALERT level G = General alerts; check

   1 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
   3 ALERT type 2 Indicator that the structure model may be wrong or deficient
   0 ALERT type 3 Indicator that the structure quality may be low
   1 ALERT type 4 Improvement, methodology, query or suggestion

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S1. Comment

The title compound (I) has been prepared as a minor product from the reaction of Ru₃(CO)₁₂ and 4,4'-dibromoazobenzene in refluxing n-octane; the major product is the cluster complex Ru₃(µ₃-NC₆H₄Br)₂(CO)₉ (Willis et al., 2005). Two strong ν(CO) absorptions at 2047 and 1984 cm⁻¹ in the IR spectrum of (I) are consistent with the presence of two mutually cis carbonyl groups. The crystal structure was investigated to ascertain the relative dispositions of the remaining C and N donor atoms of the two cyclometallated 4,4'-dibromoazobenzene ligands.

The complex possesses a distorted octahedral coordination at the Ru atom and the X-ray study confirms the cis-disposed carbonyl ligands (Fig. 1). The N atoms of the cyclometallated azobenzene ligands are mutually trans, and the aryl C atoms are trans to the carbonyl ligands.

For ruthenium complexes of this type, i.e. with cis monodentate ligands and two N,C-cyclometallated ligands, three different arrangements of the cyclometallated donor atoms are possible. An analogue containing azobenzene residues Ru(C₆H₄N=NPh)₂(CO)₂ (Bruce et al., 1987) and a further minor product from the present reaction (Willis et al., 2006) possesses one configuration, in which one N atom is trans to an aryl C, while the other N atom is trans to a carbonyl ligand, with the other aryl C trans to the remaining carbonyl ligand. The second possibility, in which each of the N atoms is trans to a carbonyl ligand, is seen in Ru(C₁₃H₈N)₂(CO)₂ (Patrick et al., 1983). Compound (I) has the third configuration, not previously observed for ruthenium complexes with ligands of this type.

S2. Experimental

Ru₃(CO)₁₂ (200 mg, 0.31 mmol) was added to a solution of 4,4'-dibromoazobenzene (210 mg, 0.62 mmol) in n-octane (30 ml), and the mixture heated at reflux for 4 h. The resulting brown solution was taken to dryness on a rotary evaporator, and the residue dissolved in a minimum of CH₂Cl₂ (ca 3 ml) and applied to preparative thin-layer chromatography plates. Elution with CH₂Cl₂/petrol ether (1/9) gave four bands and a heavy baseline: band 1 was yellow (R_F =)/4; band 2 was orange (R_F = 0.52); band 3 was yellow (R_F = 0.21); band 4 (R_F = 0.10) was yellow. The contents of band 4 were identified as Ru(CO)₂(C₁₂H₇Br₂N₂)₂, compound (I), (50 mg, 19%). MS (secondary ion, Cs⁺): 837 − 28n ([M − nCO]⁺, n = 0–2. IR (CH₂Cl₂): ν(CO) 2047 s, 1984 s cm⁻¹. Crystals were obtained by liquid diffusion of methanol into a dichloromethane solution.

S3. Refinement

H atoms were included at idealized positions and made to ride on their parent atoms, with C—H = 1.00 Å and U_iso(H) = 1.2U_eq(C).

Computing details

Data collection: COLLECT (Nonius, 1997); cell refinement: DENZO/SCALEPACK (Otwinowski & Minor, 1997); data reduction: DENZO/SCALEPACK; program(s) used to solve structure: SIR92 (Altomare et al., 1994); program(s) used to refine structure: CRYSTALS (Betteridge et al., 2003); molecular graphics: ORTEPII (Johnson, 1976) in TEXSAN (Molecular Structure Corporation, 1997); software used to prepare material for publication: CRYSTALS.

Figures

Fig. 1. The molecular structure of (I), showing 30% probability displacement ellipsoids. H atoms have been omitted for clarity.

(OC-6–32)-Bis[5-bromo-2-(4-bromophenyldiazenyl)phenyl]dicarbonylruthenium(II)

Crystal data

[Ru(C12H7Br2N2)2(CO)2]	F(000) = 1592
Mr = 835.11	Dx = 2.115 Mg m^−3
Monoclinic, P21/n	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2yn	Cell parameters from 32959 reflections
a = 13.5277 (2) Å	θ = 3–27°
b = 12.4006 (3) Å	µ = 6.73 mm^−1
c = 15.6585 (2) Å	T = 200 K
β = 93.176 (1)°	Block, orange
V = 2622.70 (8) Å^3	0.38 × 0.21 × 0.14 mm
Z = 4

Data collection

Nonius KappaCCD diffractometer	4200 reflections with I > 3σ(I)
Graphite monochromator	Rint = 0.05
ϕ and ω scans	θmax = 27.5°, θmin = 3.3°
Absorption correction: integration (Coppens, 1970)	h = −17→17
Tmin = 0.192, Tmax = 0.497	k = −16→16
49588 measured reflections	l = −20→20
5998 independent reflections

Refinement

Refinement on F	0 restraints
R[F^2 > 2σ(F^2)] = 0.025	w = [1-(Fo-Fc)^2/36σ^2(F)]^2/[1.39T0(x)-0.108T1(x) + 0.987T2(x)] where Ti are Chebychev polynomials and x = Fc/Fmax (Prince, 1982; Watkin, 1994)
wR(F^2) = 0.028	(Δ/σ)max = 0.002
S = 1.09	Δρmax = 0.95 e Å^−3
4200 reflections	Δρmin = −0.75 e Å^−3
334 parameters

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Ų)

	x	y	z	Uiso*/Ueq
Ru1	0.754629 (17)	0.578893 (19)	0.607309 (15)	0.0213
Br11	1.01812 (3)	0.95706 (4)	0.70555 (3)	0.0492
Br12	0.67482 (3)	0.21752 (3)	0.22049 (2)	0.0444
Br21	0.50973 (3)	0.84548 (3)	0.35052 (2)	0.0367
Br22	0.76775 (3)	0.52785 (3)	1.09337 (2)	0.0402
O1	0.5920 (2)	0.4045 (3)	0.5985 (2)	0.0552
O2	0.9309 (2)	0.4522 (3)	0.68953 (19)	0.0492
N11	0.80505 (18)	0.5535 (2)	0.48647 (15)	0.0227
N12	0.87088 (19)	0.6155 (2)	0.45750 (16)	0.0261
N21	0.70005 (18)	0.6453 (2)	0.71766 (16)	0.0227
N22	0.63669 (19)	0.7219 (2)	0.71081 (16)	0.0255
C1	0.6526 (3)	0.4669 (3)	0.6022 (2)	0.0305
C2	0.8628 (2)	0.4942 (3)	0.6614 (2)	0.0287
C111	0.9015 (2)	0.6964 (3)	0.5152 (2)	0.0268
C112	0.8612 (2)	0.6994 (2)	0.59614 (19)	0.0243
C113	0.8980 (2)	0.7774 (3)	0.6528 (2)	0.0273
C114	0.9683 (2)	0.8511 (3)	0.6269 (2)	0.0316
C115	1.0043 (3)	0.8503 (3)	0.5457 (2)	0.0347
C116	0.9710 (2)	0.7713 (3)	0.4890 (2)	0.0329
C121	0.7747 (2)	0.4695 (2)	0.42717 (18)	0.0239
C122	0.6744 (2)	0.4515 (3)	0.4089 (2)	0.0287
C123	0.6446 (3)	0.3752 (3)	0.3480 (2)	0.0309
C124	0.7156 (3)	0.3172 (3)	0.30732 (19)	0.0321
C125	0.8153 (3)	0.3324 (3)	0.3269 (2)	0.0374
C126	0.8453 (3)	0.4102 (3)	0.3865 (2)	0.0334
C211	0.6092 (2)	0.7485 (2)	0.62670 (19)	0.0241
C212	0.6529 (2)	0.6940 (2)	0.5592 (2)	0.0238
C213	0.6234 (2)	0.7251 (3)	0.4763 (2)	0.0269
C214	0.5516 (2)	0.8055 (3)	0.4632 (2)	0.0272
C215	0.5081 (2)	0.8577 (3)	0.5299 (2)	0.0293
C216	0.5378 (2)	0.8290 (3)	0.6132 (2)	0.0297
C221	0.7250 (2)	0.6190 (3)	0.80583 (19)	0.0245
C222	0.7422 (2)	0.5121 (3)	0.8293 (2)	0.0267
C223	0.7555 (2)	0.4849 (3)	0.9152 (2)	0.0292
C224	0.7540 (2)	0.5655 (3)	0.97620 (19)	0.0294
C225	0.7416 (3)	0.6736 (3)	0.9538 (2)	0.0335
C226	0.7258 (3)	0.6992 (3)	0.8680 (2)	0.0303
H1131	0.8743	0.7809	0.7121	0.0327*
H1151	1.0531	0.9057	0.5285	0.0417*
H1161	0.9961	0.7677	0.4302	0.0395*
H1221	0.6240	0.4933	0.4394	0.0344*
H1231	0.5727	0.3622	0.3337	0.0370*
H1251	0.8655	0.2878	0.2984	0.0452*
H1261	0.9174	0.4234	0.4001	0.0401*
H2131	0.6533	0.6901	0.4263	0.0322*
H2151	0.4566	0.9146	0.5184	0.0350*
H2161	0.5084	0.8654	0.6629	0.0357*
H2221	0.7450	0.4550	0.7844	0.0321*
H2231	0.7660	0.4080	0.9328	0.0351*
H2251	0.7440	0.7312	0.9985	0.0402*
H2261	0.7149	0.7761	0.8506	0.0363*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
Ru1	0.02339 (11)	0.01940 (11)	0.02132 (11)	0.00000 (9)	0.00195 (8)	0.00054 (9)
Br11	0.0421 (2)	0.0513 (2)	0.0549 (2)	−0.01992 (18)	0.00908 (17)	−0.02564 (19)
Br12	0.0650 (3)	0.0387 (2)	0.02878 (17)	−0.00613 (18)	−0.00311 (16)	−0.01149 (14)
Br21	0.04012 (19)	0.03902 (19)	0.02996 (17)	0.00306 (15)	−0.00832 (14)	0.00638 (14)
Br22	0.0427 (2)	0.0545 (2)	0.02356 (16)	0.00860 (17)	0.00230 (13)	0.00586 (14)
O1	0.0595 (18)	0.0520 (18)	0.0551 (18)	−0.0338 (15)	0.0127 (14)	−0.0075 (14)
O2	0.0369 (14)	0.0555 (17)	0.0547 (16)	0.0144 (13)	−0.0012 (12)	0.0209 (14)
N11	0.0221 (12)	0.0232 (12)	0.0227 (12)	0.0014 (10)	−0.0003 (9)	0.0003 (10)
N12	0.0282 (13)	0.0270 (13)	0.0231 (12)	−0.0048 (11)	0.0009 (10)	0.0012 (10)
N21	0.0237 (12)	0.0210 (12)	0.0234 (12)	0.0000 (10)	0.0019 (9)	0.0014 (10)
N22	0.0275 (13)	0.0219 (12)	0.0272 (13)	0.0012 (10)	0.0021 (10)	0.0007 (10)
C1	0.0355 (17)	0.0271 (16)	0.0294 (16)	0.0003 (14)	0.0064 (13)	−0.0020 (13)
C2	0.0345 (17)	0.0275 (16)	0.0244 (14)	−0.0019 (13)	0.0030 (13)	0.0037 (12)
C111	0.0271 (15)	0.0273 (15)	0.0258 (14)	−0.0029 (12)	−0.0006 (12)	0.0015 (12)
C112	0.0234 (14)	0.0224 (15)	0.0268 (14)	0.0020 (11)	−0.0019 (11)	0.0031 (12)
C113	0.0267 (15)	0.0290 (16)	0.0261 (15)	0.0003 (13)	−0.0001 (12)	−0.0019 (12)
C114	0.0267 (15)	0.0294 (17)	0.0386 (18)	−0.0034 (13)	−0.0008 (13)	−0.0080 (14)
C115	0.0304 (17)	0.0359 (18)	0.0380 (18)	−0.0104 (14)	0.0028 (14)	0.0007 (14)
C116	0.0317 (17)	0.0382 (19)	0.0290 (16)	−0.0079 (14)	0.0029 (13)	0.0006 (14)
C121	0.0304 (15)	0.0205 (14)	0.0209 (13)	0.0005 (12)	0.0004 (11)	0.0003 (11)
C122	0.0308 (16)	0.0264 (15)	0.0288 (15)	0.0001 (13)	0.0006 (12)	−0.0028 (13)
C123	0.0320 (16)	0.0282 (16)	0.0322 (16)	−0.0045 (14)	−0.0012 (13)	0.0003 (13)
C124	0.049 (2)	0.0268 (16)	0.0199 (14)	−0.0038 (14)	−0.0004 (13)	−0.0033 (12)
C125	0.044 (2)	0.0368 (19)	0.0324 (17)	0.0027 (16)	0.0086 (15)	−0.0104 (15)
C126	0.0310 (16)	0.0361 (19)	0.0333 (16)	0.0006 (14)	0.0029 (13)	−0.0037 (14)
C211	0.0239 (14)	0.0228 (14)	0.0256 (14)	0.0009 (11)	0.0018 (11)	0.0003 (11)
C212	0.0231 (14)	0.0206 (14)	0.0273 (14)	−0.0002 (11)	−0.0002 (11)	0.0032 (12)
C213	0.0285 (15)	0.0245 (15)	0.0275 (15)	0.0009 (12)	−0.0010 (12)	0.0016 (12)
C214	0.0251 (14)	0.0254 (15)	0.0305 (16)	−0.0035 (12)	−0.0036 (12)	0.0034 (13)
C215	0.0254 (15)	0.0283 (16)	0.0337 (16)	0.0042 (12)	−0.0026 (12)	0.0012 (13)
C216	0.0293 (16)	0.0273 (16)	0.0326 (16)	0.0014 (13)	0.0033 (13)	−0.0002 (13)
C221	0.0244 (14)	0.0271 (15)	0.0218 (14)	0.0001 (12)	0.0007 (11)	0.0019 (12)
C222	0.0314 (16)	0.0240 (15)	0.0248 (14)	0.0021 (12)	0.0017 (12)	−0.0007 (12)
C223	0.0304 (16)	0.0281 (16)	0.0292 (16)	0.0025 (13)	0.0022 (13)	0.0033 (13)
C224	0.0264 (14)	0.0403 (19)	0.0216 (14)	0.0037 (13)	0.0022 (11)	0.0004 (13)
C225	0.0416 (19)	0.0324 (18)	0.0264 (16)	0.0033 (15)	0.0009 (13)	−0.0030 (13)
C226	0.0395 (18)	0.0234 (15)	0.0280 (15)	0.0034 (13)	0.0001 (13)	−0.0025 (12)

Geometric parameters (Å, º)

Ru1—N11	2.071 (2)	C121—C126	1.388 (4)
Ru1—N21	2.086 (2)	C122—C123	1.387 (5)
Ru1—C1	1.957 (3)	C122—H1221	1.000
Ru1—C2	1.956 (3)	C123—C124	1.383 (5)
Ru1—C112	2.090 (3)	C123—H1231	1.000
Ru1—C212	2.093 (3)	C124—C125	1.380 (5)
Br11—C114	1.898 (3)	C125—C126	1.387 (5)
Br12—C124	1.897 (3)	C125—H1251	1.000
Br21—C214	1.889 (3)	C126—H1261	1.000
Br22—C224	1.892 (3)	C211—C212	1.412 (4)
O1—C1	1.127 (4)	C211—C216	1.396 (4)
O2—C2	1.127 (4)	C212—C213	1.392 (4)
N11—N12	1.279 (4)	C213—C214	1.399 (4)
N11—C121	1.439 (4)	C213—H2131	1.000
N12—C111	1.397 (4)	C214—C215	1.388 (5)
N21—N22	1.280 (4)	C215—C216	1.390 (5)
N21—C221	1.440 (4)	C215—H2151	1.000
N22—C211	1.388 (4)	C216—H2161	1.000
C111—C112	1.407 (4)	C221—C222	1.392 (4)
C111—C116	1.399 (4)	C221—C226	1.391 (4)
C112—C113	1.387 (4)	C222—C223	1.390 (4)
C113—C114	1.395 (5)	C222—H2221	1.000
C113—H1131	1.000	C223—C224	1.382 (5)
C114—C115	1.387 (5)	C223—H2231	1.000
C115—C116	1.380 (5)	C224—C225	1.394 (5)
C115—H1151	1.000	C225—C226	1.385 (5)
C116—H1161	1.000	C225—H2251	1.000
C121—C122	1.390 (4)	C226—H2261	1.000
Br11···C123^i	3.436 (4)	O2···N22^v	3.404 (4)
Br11···O1^ii	3.545 (3)	O2···C216^v	3.451 (4)
Br11···C222^ii	3.599 (3)	C113···C223^ii	3.438 (5)
Br12···N12^iii	3.092 (2)	C113···C222^ii	3.494 (5)
Br21···O1^iv	3.502 (4)	C114···C223^ii	3.483 (4)
O1···C214^iv	3.359 (5)	C114···C222^ii	3.575 (4)
O1···C213^iv	3.474 (4)	C211···C223^ii	3.537 (4)
O1···C226^v	3.562 (5)	C216···C223^ii	3.448 (4)
N11—Ru1—N21	165.18 (10)	C122—C123—C124	119.2 (3)
N11—Ru1—C1	97.02 (12)	C122—C123—H1231	120.377
N21—Ru1—C1	91.87 (12)	C124—C123—H1231	120.380
N11—Ru1—C2	92.13 (11)	Br12—C124—C123	119.1 (3)
N21—Ru1—C2	98.29 (12)	Br12—C124—C125	119.3 (3)
C1—Ru1—C2	98.38 (14)	C123—C124—C125	121.5 (3)
N11—Ru1—C112	76.62 (11)	C124—C125—C126	119.3 (3)
N21—Ru1—C112	93.71 (11)	C124—C125—H1251	120.331
C1—Ru1—C112	172.86 (12)	C126—C125—H1251	120.330
C2—Ru1—C112	85.23 (12)	C121—C126—C125	119.6 (3)
N11—Ru1—C212	91.05 (11)	C121—C126—H1261	120.177
N21—Ru1—C212	76.88 (11)	C125—C126—H1261	120.177
C1—Ru1—C212	91.21 (13)	N22—C211—C212	119.6 (3)
C2—Ru1—C212	169.44 (13)	N22—C211—C216	117.4 (3)
C112—Ru1—C212	85.72 (11)	C212—C211—C216	123.0 (3)
Ru1—N11—N12	120.3 (2)	C211—C212—Ru1	110.6 (2)
Ru1—N11—C121	127.09 (19)	C211—C212—C213	117.1 (3)
N12—N11—C121	112.7 (2)	Ru1—C212—C213	132.3 (2)
N11—N12—C111	112.9 (3)	C212—C213—C214	119.7 (3)
Ru1—N21—N22	119.32 (19)	C212—C213—H2131	120.165
Ru1—N21—C221	129.05 (19)	C214—C213—H2131	120.168
N22—N21—C221	111.6 (2)	Br21—C214—C213	119.6 (2)
N21—N22—C211	113.5 (2)	Br21—C214—C215	117.6 (2)
Ru1—C1—O1	178.1 (3)	C213—C214—C215	122.9 (3)
Ru1—C2—O2	173.6 (3)	C214—C215—C216	118.3 (3)
N12—C111—C112	119.0 (3)	C214—C215—H2151	120.849
N12—C111—C116	117.8 (3)	C216—C215—H2151	120.847
C112—C111—C116	123.1 (3)	C211—C216—C215	119.1 (3)
C111—C112—Ru1	111.1 (2)	C211—C216—H2161	120.446
C111—C112—C113	116.8 (3)	C215—C216—H2161	120.448
Ru1—C112—C113	132.1 (2)	N21—C221—C222	119.7 (3)
C112—C113—C114	119.9 (3)	N21—C221—C226	120.1 (3)
C112—C113—H1131	120.071	C222—C221—C226	120.1 (3)
C114—C113—H1131	120.069	C221—C222—C223	119.8 (3)
Br11—C114—C113	119.2 (3)	C221—C222—H2221	120.090
Br11—C114—C115	118.0 (3)	C223—C222—H2221	120.091
C113—C114—C115	122.8 (3)	C222—C223—C224	119.2 (3)
C114—C115—C116	118.4 (3)	C222—C223—H2231	120.417
C114—C115—H1151	120.790	C224—C223—H2231	120.418
C116—C115—H1151	120.790	Br22—C224—C223	119.1 (3)
C111—C116—C115	118.9 (3)	Br22—C224—C225	119.0 (2)
C111—C116—H1161	120.544	C223—C224—C225	121.8 (3)
C115—C116—H1161	120.538	C224—C225—C226	118.4 (3)
N11—C121—C122	119.3 (3)	C224—C225—H2251	120.812
N11—C121—C126	120.1 (3)	C226—C225—H2251	120.813
C122—C121—C126	120.6 (3)	C221—C226—C225	120.6 (3)
C121—C122—C123	119.7 (3)	C221—C226—H2261	119.706
C121—C122—H1221	120.171	C225—C226—H2261	119.707
C123—C122—H1221	120.170
Ru1—N11—N12—C111	0.2 (3)	N22—N21—Ru1—C212	−1.8 (2)
Ru1—N11—C121—C122	49.7 (3)	N22—N21—C221—C222	143.3 (3)
Ru1—N11—C121—C126	−132.7 (3)	N22—N21—C221—C226	−32.6 (4)
Ru1—N21—N22—C211	2.4 (3)	N22—C211—C212—C213	−179.2 (3)
Ru1—N21—C221—C222	−38.1 (4)	N22—C211—C216—C215	−179.8 (3)
Ru1—N21—C221—C226	145.9 (3)	C1—Ru1—N11—C121	−5.3 (2)
Ru1—C112—C111—N12	−2.8 (3)	C1—Ru1—N21—C221	88.9 (3)
Ru1—C112—C111—C116	176.8 (2)	C1—Ru1—C212—C211	92.4 (2)
Ru1—C112—C113—C114	−178.0 (2)	C1—Ru1—C212—C213	−88.4 (3)
Ru1—C212—C211—N22	0.2 (3)	C2—Ru1—N11—C121	93.4 (2)
Ru1—C212—C211—C216	−179.4 (2)	C2—Ru1—N21—C221	−9.8 (3)
Ru1—C212—C213—C214	179.4 (2)	C2—Ru1—C112—C111	95.4 (2)
Br11—C114—C113—C112	−179.8 (2)	C2—Ru1—C112—C113	−83.7 (3)
Br11—C114—C115—C116	177.9 (3)	C111—N12—N11—C121	−179.3 (2)
Br12—C124—C123—C122	−177.2 (3)	C111—C112—Ru1—C212	−90.0 (2)
Br12—C124—C125—C126	175.9 (3)	C111—C112—C113—C114	2.9 (4)
Br21—C214—C213—C212	−178.7 (2)	C111—C116—C115—C114	0.9 (5)
Br21—C214—C215—C216	179.8 (2)	C112—Ru1—N11—C121	178.0 (2)
Br22—C224—C223—C222	177.9 (2)	C112—Ru1—N21—C221	−95.6 (3)
Br22—C224—C225—C226	−176.3 (3)	C112—Ru1—C212—C211	−94.1 (2)
N11—Ru1—C112—C111	2.1 (2)	C112—Ru1—C212—C213	85.2 (3)
N11—Ru1—C112—C113	−177.1 (3)	C112—C111—C116—C115	2.0 (5)
N11—Ru1—C212—C211	−170.6 (2)	C112—C113—C114—C115	−0.2 (5)
N11—Ru1—C212—C213	8.6 (3)	C113—C112—Ru1—C212	90.8 (3)
N11—N12—C111—C112	1.8 (4)	C113—C112—C111—C116	−3.9 (4)
N11—N12—C111—C116	−177.8 (3)	C113—C114—C115—C116	−1.8 (5)
N11—C121—C122—C123	176.1 (3)	C121—N11—Ru1—C212	−96.6 (2)
N11—C121—C126—C125	−177.4 (3)	C121—C122—C123—C124	0.9 (5)
N12—N11—Ru1—C1	175.4 (2)	C121—C126—C125—C124	1.7 (5)
N12—N11—Ru1—C2	−85.9 (2)	C122—C121—C126—C125	0.1 (5)
N12—N11—Ru1—C112	−1.3 (2)	C122—C123—C124—C125	1.0 (5)
N12—N11—Ru1—C212	84.0 (2)	C123—C122—C121—C126	−1.5 (5)
N12—N11—C121—C122	−130.9 (3)	C123—C124—C125—C126	−2.3 (5)
N12—N11—C121—C126	46.7 (4)	C211—N22—N21—C221	−178.9 (2)
N12—C111—C112—C113	176.5 (3)	C211—C212—C213—C214	−1.4 (4)
N12—C111—C116—C115	−178.3 (3)	C211—C216—C215—C214	−0.6 (5)
N21—Ru1—C112—C111	−166.6 (2)	C212—Ru1—N21—C221	179.7 (3)
N21—Ru1—C112—C113	14.3 (3)	C212—C211—C216—C215	−0.2 (4)
N21—Ru1—C212—C211	0.8 (2)	C212—C213—C214—C215	0.7 (5)
N21—Ru1—C212—C213	180.0 (3)	C213—C212—C211—C216	1.3 (4)
N21—N22—C211—C212	−1.6 (4)	C213—C214—C215—C216	0.4 (5)
N21—N22—C211—C216	178.0 (3)	C221—C222—C223—C224	−1.7 (4)
N21—C221—C222—C223	−172.9 (3)	C221—C226—C225—C224	−1.7 (6)
N21—C221—C226—C225	174.6 (3)	C222—C221—C226—C225	−1.3 (5)
N22—N21—Ru1—C1	−92.6 (2)	C222—C223—C224—C225	−1.4 (4)
N22—N21—Ru1—C2	168.6 (2)	C223—C222—C221—C226	3.1 (4)
N22—N21—Ru1—C112	82.9 (2)	C223—C224—C225—C226	3.1 (5)

Symmetry codes: (i) x+1/2, −y+3/2, z+1/2; (ii) −x+3/2, y+1/2, −z+3/2; (iii) −x+3/2, y−1/2, −z+1/2; (iv) −x+1, −y+1, −z+1; (v) −x+3/2, y−1/2, −z+3/2.