Studies of κ²- and κ³-tri­pyridyl­amine complexes of ruthenium and π-stacking by pyridyls

The reaction of tris­(pyridin-2-yl)amine with [CyRuCl₂]₂ (Cy = p-iso­propyl­toluene or cymene) in refluxing diglyme led to the formation of cis-[RuCl₂{κ²-(2-py)₃N}₂]·CHCl₃ (1a) after recrystallization from chloro­form/pentane, or cis-di­chlorido­bis­[tris­(pyridin-2-yl)amine-κ²N,N′]ruthenium(II) di­chloro­methane di­solvate, [RuCl₂(C₁₅H₁₂N₄)₂]·2CH₂Cl₂ or cis-[RuCl₂{κ²-(2-py)₃N}₂]·2CH₂Cl₂ (1b). Treatment of 1a with one equivalent of silver(I) hexa­fluorido­anti­monate in di­chloro­methane gave [RuCl{κ²-(2-py)₃N}{κ³-(2-py)₃N}][SbF₆]·CH₂Cl₂ (2a). Crystallization of 2a from chloro­form provided chlorido­[tris­(pyridin-2-yl)amine-κ²N,N′][tris­(pyridin-2-yl)amine-κ³N,N′,N′′]ruthenium(II) hexa­fluorido­anti­monate chloro­form monosolvate, [RuCl(C₁₅H₁₂N₄)₂][SbF₆]·CHCl₃ or [RuCl{κ²-(2-py)₃N}{κ³-(2-py)₃N}][SbF₆]·CHCl₃ (2b). Complex 2a reacted with a further equivalent of silver(I) hexa­fluorido­anti­monate to give [Ru{κ³-(2-py)₃N}₂][SbF₆]₂ (3). The reaction of (2-py)₃N with [CyRuCl₂]₂ in di­chloro­methane followed by treatment with excess sodium hexa­fluorido­anti­monate gave the known complex [CyRuCl{κ²-(2-py)₃N}][SbF₆] (4). Complex 2 is a rare example of a complex containing both κ²- and κ³-(2-py)₃N. Intra­molecular π-stacking inter­actions determine the orientation of the free pyridyl in the κ² complexes. An inter­esting encapsulation of methyl­ene chloride hydrogen-bonded tetra­mers was noted in one case.

Computing details

Dichloridobis[tris(pyridin-2-yl)amine-κ²N,N']ruthenium(II) dichloromethane disolvate (1b)

Crystal data

[RuCl2(C15H12N4)2]·2CH2Cl2	Z = 2
Mr = 838.39	F(000) = 844
Triclinic, P1	Dx = 1.706 Mg m^−3
a = 11.2435 (7) Å	Mo Kα radiation, λ = 0.71073 Å
b = 11.4038 (7) Å	Cell parameters from 15256 reflections
c = 13.6340 (7) Å	θ = 2.8–30.5°
α = 74.278 (5)°	µ = 1.01 mm^−1
β = 75.995 (5)°	T = 93 K
γ = 84.642 (5)°	Prism, orange
V = 1631.99 (17) Å^3	0.37 × 0.29 × 0.2 mm

Data collection

Rigaku Mercury275R CCD diffractometer	6726 reflections with I > 2σ(I)
Detector resolution: 6.8 pixels mm^-1	Rint = 0.093
ω scans	θmax = 30.5°, θmin = 2.7°
Absorption correction: multi-scan (CrysAlis PRO; Rigaku OD, 2019)	h = −15→16
Tmin = 0.926, Tmax = 1.000	k = −16→16
34353 measured reflections	l = −19→19
9877 independent reflections

Refinement

Refinement on F^2	Primary atom site location: dual
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F^2 > 2σ(F^2)] = 0.061	H-atom parameters constrained
wR(F^2) = 0.108	w = 1/[σ^2(Fo^2) + (0.0266P)^2 + 3.9087P] where P = (Fo^2 + 2Fc^2)/3
S = 1.03	(Δ/σ)max = 0.001
9877 reflections	Δρmax = 0.97 e Å^−3
424 parameters	Δρmin = −0.76 e Å^−3
0 restraints

Special details

Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes.

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

	x	y	z	Uiso*/Ueq
Ru1	0.76400 (3)	0.73839 (3)	0.50380 (2)	0.01125 (8)
Cl1	0.96002 (8)	0.71921 (8)	0.38718 (7)	0.01494 (18)
Cl2	0.66580 (8)	0.80970 (8)	0.35919 (7)	0.01553 (19)
Cl3	1.14367 (11)	0.95770 (11)	0.88069 (9)	0.0323 (3)
Cl4	0.89342 (11)	0.99325 (10)	0.85424 (9)	0.0312 (3)
Cl5	1.37129 (11)	1.34020 (11)	0.86258 (9)	0.0361 (3)
Cl6	1.10635 (11)	1.32412 (11)	0.92797 (9)	0.0358 (3)
N1	0.8092 (3)	0.9115 (3)	0.4951 (2)	0.0123 (6)
N2	0.8448 (3)	0.6834 (3)	0.6271 (2)	0.0123 (6)
N3	0.6383 (3)	1.0142 (3)	0.7273 (3)	0.0257 (8)
N4	0.7763 (3)	0.8649 (3)	0.6766 (2)	0.0127 (6)
N5	0.5991 (3)	0.7491 (3)	0.6038 (2)	0.0122 (6)
N6	0.7166 (3)	0.5678 (3)	0.5075 (2)	0.0123 (6)
N7	0.6217 (3)	0.5179 (3)	0.8553 (3)	0.0220 (7)
N8	0.6141 (3)	0.5413 (3)	0.6825 (2)	0.0140 (6)
C1	0.8431 (3)	0.9909 (3)	0.4010 (3)	0.0158 (8)
H1	0.841044	0.966068	0.340388	0.019*
C2	0.8801 (3)	1.1051 (3)	0.3888 (3)	0.0162 (8)
H2	0.899673	1.159809	0.321172	0.019*
C3	0.8888 (3)	1.1405 (3)	0.4754 (3)	0.0179 (8)
H3	0.916364	1.219205	0.468523	0.021*
C4	0.8571 (3)	1.0602 (3)	0.5717 (3)	0.0146 (7)
H4	0.863908	1.081662	0.632727	0.017*
C5	0.8150 (3)	0.9472 (3)	0.5787 (3)	0.0129 (7)
C6	0.5434 (4)	1.0466 (4)	0.7950 (4)	0.0316 (11)
H6	0.512007	1.128064	0.778063	0.038*
C7	0.4882 (4)	0.9701 (5)	0.8872 (4)	0.0311 (11)
H7	0.420620	0.997012	0.933752	0.037*
C8	0.5344 (4)	0.8523 (4)	0.9101 (3)	0.0277 (10)
H8	0.498303	0.796129	0.973571	0.033*
C9	0.6313 (4)	0.8157 (3)	0.8427 (3)	0.0176 (8)
H9	0.664006	0.734654	0.858153	0.021*
C10	0.6803 (3)	0.8989 (3)	0.7520 (3)	0.0156 (8)
C11	0.9096 (3)	0.5772 (3)	0.6425 (3)	0.0146 (7)
H11	0.921410	0.531855	0.591715	0.017*
C12	0.9591 (3)	0.5317 (3)	0.7280 (3)	0.0161 (8)
H12	1.001666	0.454927	0.737285	0.019*
C13	0.9465 (3)	0.5987 (3)	0.8004 (3)	0.0175 (8)
H13	0.979346	0.568807	0.860782	0.021*
C14	0.8857 (3)	0.7091 (3)	0.7833 (3)	0.0158 (8)
H14	0.877527	0.757892	0.831152	0.019*
C15	0.8363 (3)	0.7496 (3)	0.6970 (3)	0.0137 (7)
C16	0.7464 (3)	0.5277 (3)	0.4209 (3)	0.0144 (7)
H16	0.797867	0.575801	0.360192	0.017*
C17	0.7062 (3)	0.4205 (3)	0.4161 (3)	0.0176 (8)
H17	0.733441	0.392770	0.354419	0.021*
C18	0.6264 (3)	0.3535 (3)	0.5008 (3)	0.0184 (8)
H18	0.595363	0.280010	0.498074	0.022*
C19	0.5921 (3)	0.3942 (3)	0.5895 (3)	0.0170 (8)
H19	0.535170	0.350752	0.648962	0.020*
C20	0.6420 (3)	0.5000 (3)	0.5910 (3)	0.0128 (7)
C21	0.6584 (4)	0.4546 (4)	0.9414 (3)	0.0267 (10)
H21	0.639614	0.487612	1.000517	0.032*
C22	0.7203 (4)	0.3469 (4)	0.9493 (3)	0.0298 (10)
H22	0.745311	0.305038	1.011724	0.036*
C23	0.7458 (4)	0.2998 (4)	0.8640 (4)	0.0311 (11)
H23	0.788795	0.223605	0.867265	0.037*
C24	0.7103 (4)	0.3607 (3)	0.7744 (3)	0.0226 (9)
H24	0.727817	0.328566	0.714851	0.027*
C25	0.6479 (3)	0.4713 (3)	0.7736 (3)	0.0146 (7)
C26	0.5354 (3)	0.8562 (3)	0.5945 (3)	0.0149 (7)
H26	0.567244	0.923808	0.538769	0.018*
C27	0.4275 (3)	0.8713 (3)	0.6615 (3)	0.0147 (7)
H27	0.386480	0.948849	0.654234	0.018*
C28	0.3784 (3)	0.7724 (4)	0.7402 (3)	0.0169 (8)
H28	0.302883	0.780619	0.787888	0.020*
C29	0.4402 (3)	0.6625 (3)	0.7484 (3)	0.0165 (8)
H29	0.407755	0.592811	0.801363	0.020*
C30	0.5503 (3)	0.6541 (3)	0.6789 (3)	0.0134 (7)
C31	1.0237 (4)	1.0647 (4)	0.8564 (3)	0.0245 (9)
H31A	1.002534	1.109425	0.911565	0.029*
H31B	1.051384	1.124580	0.788381	0.029*
C32	1.2459 (4)	1.2483 (4)	0.8893 (4)	0.0278 (10)
H32A	1.254901	1.174403	0.945609	0.033*
H32B	1.244774	1.221948	0.826080	0.033*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
Ru1	0.01253 (15)	0.01005 (15)	0.01226 (14)	−0.00182 (11)	−0.00308 (11)	−0.00394 (11)
Cl1	0.0144 (4)	0.0150 (4)	0.0155 (4)	−0.0022 (3)	−0.0007 (3)	−0.0060 (4)
Cl2	0.0191 (5)	0.0143 (4)	0.0156 (4)	−0.0009 (4)	−0.0076 (4)	−0.0044 (4)
Cl3	0.0353 (6)	0.0345 (6)	0.0242 (5)	0.0071 (5)	−0.0049 (5)	−0.0069 (5)
Cl4	0.0423 (7)	0.0231 (5)	0.0348 (6)	−0.0018 (5)	−0.0160 (5)	−0.0119 (5)
Cl5	0.0419 (7)	0.0314 (6)	0.0354 (6)	−0.0143 (5)	0.0000 (5)	−0.0127 (5)
Cl6	0.0376 (7)	0.0344 (6)	0.0377 (7)	0.0091 (5)	−0.0129 (5)	−0.0126 (5)
N1	0.0091 (14)	0.0130 (15)	0.0152 (15)	0.0023 (12)	−0.0031 (12)	−0.0051 (12)
N2	0.0139 (15)	0.0094 (15)	0.0134 (15)	−0.0048 (12)	−0.0025 (12)	−0.0017 (12)
N3	0.031 (2)	0.0227 (19)	0.028 (2)	0.0054 (16)	−0.0105 (16)	−0.0126 (16)
N4	0.0179 (16)	0.0076 (14)	0.0134 (15)	−0.0005 (12)	−0.0052 (12)	−0.0027 (12)
N5	0.0143 (15)	0.0110 (15)	0.0139 (15)	−0.0011 (12)	−0.0056 (12)	−0.0052 (12)
N6	0.0101 (14)	0.0137 (15)	0.0132 (15)	−0.0004 (12)	−0.0042 (12)	−0.0024 (12)
N7	0.0280 (19)	0.0210 (18)	0.0160 (17)	−0.0002 (15)	−0.0027 (14)	−0.0053 (14)
N8	0.0167 (16)	0.0121 (15)	0.0132 (15)	−0.0002 (12)	−0.0031 (12)	−0.0033 (12)
C1	0.0127 (18)	0.019 (2)	0.0152 (18)	−0.0004 (15)	−0.0025 (14)	−0.0045 (15)
C2	0.0139 (18)	0.0140 (19)	0.0193 (19)	−0.0021 (15)	−0.0034 (15)	−0.0013 (15)
C3	0.0147 (19)	0.0114 (18)	0.029 (2)	−0.0012 (15)	−0.0070 (16)	−0.0046 (16)
C4	0.0135 (18)	0.0124 (18)	0.0188 (19)	0.0030 (14)	−0.0052 (15)	−0.0055 (15)
C5	0.0128 (17)	0.0086 (17)	0.0171 (18)	0.0042 (14)	−0.0054 (14)	−0.0027 (14)
C6	0.041 (3)	0.030 (3)	0.034 (3)	0.017 (2)	−0.024 (2)	−0.017 (2)
C7	0.019 (2)	0.048 (3)	0.036 (3)	0.013 (2)	−0.0082 (19)	−0.030 (2)
C8	0.028 (2)	0.038 (3)	0.018 (2)	−0.012 (2)	−0.0026 (18)	−0.0089 (19)
C9	0.022 (2)	0.0124 (18)	0.0183 (19)	0.0001 (15)	−0.0044 (16)	−0.0037 (15)
C10	0.0164 (19)	0.0178 (19)	0.0180 (19)	−0.0015 (15)	−0.0076 (15)	−0.0099 (16)
C11	0.0139 (18)	0.0129 (18)	0.0156 (18)	−0.0039 (14)	0.0005 (14)	−0.0036 (15)
C12	0.0102 (17)	0.0145 (19)	0.022 (2)	−0.0006 (14)	−0.0037 (15)	−0.0021 (16)
C13	0.0169 (19)	0.018 (2)	0.0179 (19)	−0.0015 (15)	−0.0069 (15)	−0.0030 (16)
C14	0.0204 (19)	0.0144 (19)	0.0148 (18)	−0.0006 (15)	−0.0067 (15)	−0.0050 (15)
C15	0.0106 (17)	0.0125 (18)	0.0164 (18)	−0.0049 (14)	0.0010 (14)	−0.0031 (14)
C16	0.0133 (18)	0.0145 (19)	0.0175 (18)	0.0002 (14)	−0.0039 (14)	−0.0072 (15)
C17	0.019 (2)	0.017 (2)	0.0202 (19)	0.0012 (16)	−0.0066 (16)	−0.0095 (16)
C18	0.0175 (19)	0.0128 (19)	0.030 (2)	−0.0005 (15)	−0.0096 (17)	−0.0097 (17)
C19	0.0183 (19)	0.0081 (17)	0.023 (2)	−0.0010 (15)	−0.0058 (16)	0.0001 (15)
C20	0.0145 (18)	0.0115 (18)	0.0137 (17)	0.0014 (14)	−0.0055 (14)	−0.0039 (14)
C21	0.035 (2)	0.029 (2)	0.014 (2)	−0.003 (2)	−0.0041 (18)	−0.0036 (18)
C22	0.031 (2)	0.032 (3)	0.022 (2)	0.001 (2)	−0.0104 (19)	0.0049 (19)
C23	0.030 (2)	0.015 (2)	0.038 (3)	0.0063 (18)	−0.001 (2)	0.0024 (19)
C24	0.034 (2)	0.0125 (19)	0.020 (2)	0.0003 (17)	−0.0021 (18)	−0.0043 (16)
C25	0.0143 (18)	0.0088 (17)	0.0184 (19)	−0.0028 (14)	−0.0009 (15)	−0.0013 (14)
C26	0.0146 (18)	0.0136 (18)	0.0180 (19)	0.0018 (15)	−0.0073 (15)	−0.0041 (15)
C27	0.0170 (19)	0.0127 (18)	0.0177 (18)	0.0023 (15)	−0.0080 (15)	−0.0067 (15)
C28	0.0122 (18)	0.022 (2)	0.0195 (19)	−0.0004 (15)	−0.0028 (15)	−0.0107 (16)
C29	0.0170 (19)	0.0170 (19)	0.0147 (18)	−0.0039 (15)	−0.0036 (15)	−0.0014 (15)
C30	0.0160 (18)	0.0113 (18)	0.0156 (18)	−0.0007 (14)	−0.0054 (14)	−0.0060 (15)
C31	0.031 (2)	0.018 (2)	0.023 (2)	0.0005 (18)	−0.0010 (18)	−0.0079 (17)
C32	0.030 (2)	0.020 (2)	0.031 (2)	−0.0055 (18)	0.0015 (19)	−0.0092 (19)

Geometric parameters (Å, º)

Ru1—Cl1	2.4157 (9)	C8—H8	0.9500
Ru1—Cl2	2.4051 (9)	C8—C9	1.358 (6)
Ru1—N1	2.050 (3)	C9—H9	0.9500
Ru1—N2	2.027 (3)	C9—C10	1.365 (5)
Ru1—N5	2.033 (3)	C11—H11	0.9500
Ru1—N6	2.049 (3)	C11—C12	1.367 (5)
Cl3—C31	1.763 (4)	C12—H12	0.9500
Cl4—C31	1.752 (4)	C12—C13	1.378 (5)
Cl5—C32	1.744 (4)	C13—H13	0.9500
Cl6—C32	1.755 (4)	C13—C14	1.366 (5)
N1—C1	1.345 (5)	C14—H14	0.9500
N1—C5	1.327 (4)	C14—C15	1.370 (5)
N2—C11	1.346 (5)	C16—H16	0.9500
N2—C15	1.348 (4)	C16—C17	1.365 (5)
N3—C6	1.327 (6)	C17—H17	0.9500
N3—C10	1.337 (5)	C17—C18	1.368 (5)
N4—C5	1.403 (5)	C18—H18	0.9500
N4—C10	1.406 (5)	C18—C19	1.369 (5)
N4—C15	1.410 (5)	C19—H19	0.9500
N5—C26	1.348 (5)	C19—C20	1.384 (5)
N5—C30	1.327 (5)	C21—H21	0.9500
N6—C16	1.336 (4)	C21—C22	1.345 (6)
N6—C20	1.335 (5)	C22—H22	0.9500
N7—C21	1.338 (5)	C22—C23	1.367 (6)
N7—C25	1.320 (5)	C23—H23	0.9500
N8—C20	1.406 (4)	C23—C24	1.363 (6)
N8—C25	1.399 (5)	C24—H24	0.9500
N8—C30	1.408 (5)	C24—C25	1.384 (5)
C1—H1	0.9500	C26—H26	0.9500
C1—C2	1.359 (5)	C26—C27	1.359 (5)
C2—H2	0.9500	C27—H27	0.9500
C2—C3	1.374 (5)	C27—C28	1.379 (5)
C3—H3	0.9500	C28—H28	0.9500
C3—C4	1.368 (5)	C28—C29	1.366 (5)
C4—H4	0.9500	C29—H29	0.9500
C4—C5	1.386 (5)	C29—C30	1.378 (5)
C6—H6	0.9500	C31—H31A	0.9900
C6—C7	1.362 (7)	C31—H31B	0.9900
C7—H7	0.9500	C32—H32A	0.9900
C7—C8	1.376 (6)	C32—H32B	0.9900
Cl2—Ru1—Cl1	91.45 (3)	C11—C12—C13	119.1 (4)
N1—Ru1—Cl1	88.02 (8)	C13—C12—H12	120.5
N1—Ru1—Cl2	92.07 (9)	C12—C13—H13	120.8
N2—Ru1—Cl1	89.57 (9)	C14—C13—C12	118.4 (3)
N2—Ru1—Cl2	178.12 (9)	C14—C13—H13	120.8
N2—Ru1—N1	86.39 (12)	C13—C14—H14	120.0
N2—Ru1—N5	89.74 (12)	C13—C14—C15	120.0 (3)
N2—Ru1—N6	95.74 (11)	C15—C14—H14	120.0
N5—Ru1—Cl1	178.31 (9)	N2—C15—N4	117.1 (3)
N5—Ru1—Cl2	89.28 (9)	N2—C15—C14	122.2 (3)
N5—Ru1—N1	93.48 (12)	C14—C15—N4	120.7 (3)
N5—Ru1—N6	86.78 (12)	N6—C16—H16	118.6
N6—Ru1—Cl1	91.76 (9)	N6—C16—C17	122.8 (4)
N6—Ru1—Cl2	85.81 (8)	C17—C16—H16	118.6
N6—Ru1—N1	177.86 (12)	C16—C17—H17	120.3
C1—N1—Ru1	119.7 (2)	C16—C17—C18	119.4 (4)
C5—N1—Ru1	122.6 (2)	C18—C17—H17	120.3
C5—N1—C1	117.5 (3)	C17—C18—H18	120.6
C11—N2—Ru1	120.5 (2)	C17—C18—C19	118.7 (3)
C11—N2—C15	117.2 (3)	C19—C18—H18	120.6
C15—N2—Ru1	122.4 (2)	C18—C19—H19	120.6
C6—N3—C10	117.1 (4)	C18—C19—C20	118.7 (4)
C5—N4—C10	119.8 (3)	C20—C19—H19	120.6
C5—N4—C15	118.7 (3)	N6—C20—N8	116.9 (3)
C10—N4—C15	121.6 (3)	N6—C20—C19	122.6 (3)
C26—N5—Ru1	119.6 (2)	C19—C20—N8	120.4 (3)
C30—N5—Ru1	122.6 (2)	N7—C21—H21	118.1
C30—N5—C26	117.8 (3)	N7—C21—C22	123.8 (4)
C16—N6—Ru1	120.4 (2)	C22—C21—H21	118.1
C20—N6—Ru1	121.6 (2)	C21—C22—H22	121.2
C20—N6—C16	117.5 (3)	C21—C22—C23	117.5 (4)
C25—N7—C21	117.7 (4)	C23—C22—H22	121.2
C20—N8—C30	117.5 (3)	C22—C23—H23	119.5
C25—N8—C20	120.7 (3)	C24—C23—C22	120.9 (4)
C25—N8—C30	121.8 (3)	C24—C23—H23	119.5
N1—C1—H1	118.5	C23—C24—H24	121.3
N1—C1—C2	123.0 (3)	C23—C24—C25	117.3 (4)
C2—C1—H1	118.5	C25—C24—H24	121.3
C1—C2—H2	120.4	N7—C25—N8	117.1 (3)
C1—C2—C3	119.1 (4)	N7—C25—C24	122.7 (4)
C3—C2—H2	120.4	C24—C25—N8	120.2 (3)
C2—C3—H3	120.6	N5—C26—H26	118.6
C4—C3—C2	118.8 (3)	N5—C26—C27	122.7 (4)
C4—C3—H3	120.6	C27—C26—H26	118.6
C3—C4—H4	120.5	C26—C27—H27	120.5
C3—C4—C5	118.9 (3)	C26—C27—C28	119.0 (3)
C5—C4—H4	120.5	C28—C27—H27	120.5
N1—C5—N4	117.1 (3)	C27—C28—H28	120.6
N1—C5—C4	122.5 (3)	C29—C28—C27	118.8 (4)
C4—C5—N4	120.4 (3)	C29—C28—H28	120.6
N3—C6—H6	118.0	C28—C29—H29	120.4
N3—C6—C7	124.0 (4)	C28—C29—C30	119.2 (4)
C7—C6—H6	118.0	C30—C29—H29	120.4
C6—C7—H7	121.4	N5—C30—N8	116.8 (3)
C6—C7—C8	117.2 (4)	N5—C30—C29	122.5 (3)
C8—C7—H7	121.4	C29—C30—N8	120.6 (3)
C7—C8—H8	119.7	Cl3—C31—H31A	109.4
C9—C8—C7	120.5 (4)	Cl3—C31—H31B	109.4
C9—C8—H8	119.7	Cl4—C31—Cl3	111.2 (2)
C8—C9—H9	121.0	Cl4—C31—H31A	109.4
C8—C9—C10	118.0 (4)	Cl4—C31—H31B	109.4
C10—C9—H9	121.0	H31A—C31—H31B	108.0
N3—C10—N4	116.1 (3)	Cl5—C32—Cl6	112.2 (2)
N3—C10—C9	123.2 (4)	Cl5—C32—H32A	109.2
C9—C10—N4	120.7 (3)	Cl5—C32—H32B	109.2
N2—C11—H11	118.5	Cl6—C32—H32A	109.2
N2—C11—C12	123.0 (3)	Cl6—C32—H32B	109.2
C12—C11—H11	118.5	H32A—C32—H32B	107.9
C11—C12—H12	120.5
Ru1—N1—C1—C2	−176.7 (3)	C11—C12—C13—C14	−0.6 (5)
Ru1—N1—C5—N4	−6.5 (4)	C12—C13—C14—C15	1.5 (6)
Ru1—N1—C5—C4	173.5 (3)	C13—C14—C15—N2	0.4 (6)
Ru1—N2—C11—C12	−175.5 (3)	C13—C14—C15—N4	−178.2 (3)
Ru1—N2—C15—N4	−4.9 (4)	C15—N2—C11—C12	4.2 (5)
Ru1—N2—C15—C14	176.5 (3)	C15—N4—C5—N1	59.2 (4)
Ru1—N5—C26—C27	−176.9 (3)	C15—N4—C5—C4	−120.8 (4)
Ru1—N5—C30—N8	−4.2 (4)	C15—N4—C10—N3	174.0 (3)
Ru1—N5—C30—C29	178.0 (3)	C15—N4—C10—C9	−8.6 (5)
Ru1—N6—C16—C17	−172.9 (3)	C16—N6—C20—N8	178.2 (3)
Ru1—N6—C20—N8	−10.5 (4)	C16—N6—C20—C19	−2.5 (5)
Ru1—N6—C20—C19	168.8 (3)	C16—C17—C18—C19	−2.0 (6)
N1—C1—C2—C3	2.9 (6)	C17—C18—C19—C20	−1.7 (6)
N2—C11—C12—C13	−2.3 (5)	C18—C19—C20—N6	4.1 (6)
N3—C6—C7—C8	−0.4 (7)	C18—C19—C20—N8	−176.6 (3)
N5—C26—C27—C28	−2.4 (5)	C20—N6—C16—C17	−1.5 (5)
N6—C16—C17—C18	3.8 (6)	C20—N8—C25—N7	178.0 (3)
N7—C21—C22—C23	−0.6 (7)	C20—N8—C25—C24	0.6 (5)
C1—N1—C5—N4	178.3 (3)	C20—N8—C30—N5	−54.5 (4)
C1—N1—C5—C4	−1.7 (5)	C20—N8—C30—C29	123.2 (4)
C1—C2—C3—C4	−1.5 (6)	C21—N7—C25—N8	−177.0 (3)
C2—C3—C4—C5	−1.3 (5)	C21—N7—C25—C24	0.3 (6)
C3—C4—C5—N1	3.0 (5)	C21—C22—C23—C24	0.5 (7)
C3—C4—C5—N4	−177.0 (3)	C22—C23—C24—C25	0.0 (6)
C5—N1—C1—C2	−1.3 (5)	C23—C24—C25—N7	−0.4 (6)
C5—N4—C10—N3	−5.4 (5)	C23—C24—C25—N8	176.9 (4)
C5—N4—C10—C9	172.0 (3)	C25—N7—C21—C22	0.2 (6)
C5—N4—C15—N2	−52.7 (4)	C25—N8—C20—N6	−117.6 (4)
C5—N4—C15—C14	125.9 (4)	C25—N8—C20—C19	63.0 (5)
C6—N3—C10—N4	176.5 (3)	C25—N8—C30—N5	126.2 (4)
C6—N3—C10—C9	−0.8 (6)	C25—N8—C30—C29	−56.1 (5)
C6—C7—C8—C9	0.2 (6)	C26—N5—C30—N8	175.6 (3)
C7—C8—C9—C10	−0.3 (6)	C26—N5—C30—C29	−2.1 (5)
C8—C9—C10—N3	0.7 (6)	C26—C27—C28—C29	0.2 (5)
C8—C9—C10—N4	−176.6 (3)	C27—C28—C29—C30	0.8 (5)
C10—N3—C6—C7	0.7 (6)	C28—C29—C30—N5	0.1 (5)
C10—N4—C5—N1	−121.4 (4)	C28—C29—C30—N8	−177.6 (3)
C10—N4—C5—C4	58.6 (5)	C30—N5—C26—C27	3.3 (5)
C10—N4—C15—N2	127.9 (3)	C30—N8—C20—N6	63.1 (4)
C10—N4—C15—C14	−53.5 (5)	C30—N8—C20—C19	−116.3 (4)
C11—N2—C15—N4	175.4 (3)	C30—N8—C25—N7	−2.7 (5)
C11—N2—C15—C14	−3.2 (5)	C30—N8—C25—C24	179.8 (3)

Chlorido[tris(pyridin-2-yl)amine-κ²N,N'][tris(pyridin-2-yl)amine-κ³N,N',N'']ruthenium(II) hexafluoridoantimonate chloroform monosolvate (2b)

Crystal data

[RuCl(C15H12N4)2][SbF6]·CHCl3	F(000) = 1936
Mr = 988.21	Dx = 1.855 Mg m^−3
Monoclinic, P21/n	Mo Kα radiation, λ = 0.71073 Å
a = 8.3209 (3) Å	Cell parameters from 8950 reflections
b = 27.3213 (10) Å	θ = 3.3–30.4°
c = 15.7839 (6) Å	µ = 1.56 mm^−1
β = 99.554 (4)°	T = 93 K
V = 3538.5 (2) Å^3	Needle, yellow
Z = 4	0.2 × 0.04 × 0.01 mm

Data collection

Dectris Pilatus 3R diffractometer	6339 reflections with I > 2σ(I)
Detector resolution: 5.8 pixels mm^-1	Rint = 0.067
ω scans	θmax = 28.3°, θmin = 2.7°
Absorption correction: multi-scan (CrysAlis PRO; Rigaku OD, 2019)	h = −10→11
Tmin = 0.783, Tmax = 1.000	k = −36→36
32718 measured reflections	l = −21→21
8658 independent reflections

Refinement

Refinement on F^2	Primary atom site location: iterative
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F^2 > 2σ(F^2)] = 0.048	H-atom parameters constrained
wR(F^2) = 0.081	w = 1/[σ^2(Fo^2) + (0.0259P)^2 + 4.6355P] where P = (Fo^2 + 2Fc^2)/3
S = 1.08	(Δ/σ)max = 0.001
8658 reflections	Δρmax = 0.98 e Å^−3
460 parameters	Δρmin = −1.31 e Å^−3
0 restraints

Special details

Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes.

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

	x	y	z	Uiso*/Ueq
Sb1	0.69166 (3)	0.62728 (2)	−0.05383 (2)	0.01521 (7)
F1	0.6827 (4)	0.59602 (10)	0.05068 (15)	0.0327 (7)
F2	0.5627 (3)	0.67836 (9)	−0.02234 (18)	0.0328 (7)
F3	0.8788 (3)	0.66146 (10)	−0.00166 (16)	0.0287 (6)
F4	0.8247 (3)	0.57702 (10)	−0.08400 (18)	0.0355 (7)
F5	0.5049 (3)	0.59389 (11)	−0.10526 (17)	0.0349 (7)
F6	0.7015 (4)	0.65920 (12)	−0.15811 (16)	0.0418 (8)
Ru1	0.58927 (4)	0.60754 (2)	0.30593 (2)	0.00852 (7)
Cl1	0.77395 (11)	0.59764 (3)	0.44096 (5)	0.01372 (19)
N2	0.7417 (4)	0.56320 (12)	0.24889 (19)	0.0107 (6)
N3	0.4391 (4)	0.60839 (12)	0.18936 (19)	0.0115 (6)
N1	0.4703 (4)	0.54419 (11)	0.32919 (19)	0.0113 (7)
N4	0.4977 (4)	0.52254 (12)	0.18626 (18)	0.0115 (7)
N5	0.7063 (4)	0.67232 (12)	0.28082 (19)	0.0115 (7)
N6	0.4277 (4)	0.65211 (12)	0.35747 (19)	0.0117 (7)
N8	0.6459 (4)	0.70582 (12)	0.40989 (19)	0.0123 (7)
N7	0.8885 (4)	0.72276 (13)	0.5000 (2)	0.0177 (7)
C6	0.9055 (5)	0.56764 (15)	0.2601 (2)	0.0141 (8)
H6	0.957103	0.592094	0.297909	0.017*
C7	0.9997 (5)	0.53763 (15)	0.2181 (3)	0.0185 (9)
H7	1.114568	0.541992	0.226651	0.022*
C8	0.9284 (5)	0.50120 (15)	0.1636 (2)	0.0185 (9)
H8	0.992479	0.480445	0.134202	0.022*
C9	0.7597 (5)	0.49589 (15)	0.1530 (2)	0.0152 (8)
H9	0.706172	0.470935	0.117000	0.018*
C10	0.6719 (5)	0.52755 (14)	0.1958 (2)	0.0118 (8)
C11	0.3591 (5)	0.64812 (15)	0.1527 (2)	0.0162 (8)
H11	0.378994	0.678958	0.180210	0.019*
C12	0.2496 (5)	0.64568 (16)	0.0766 (2)	0.0186 (9)
H12	0.195487	0.674313	0.052487	0.022*
C13	0.2198 (5)	0.60054 (17)	0.0360 (3)	0.0218 (10)
H13	0.143533	0.597921	−0.015685	0.026*
C14	0.3023 (5)	0.55957 (16)	0.0716 (2)	0.0158 (8)
H14	0.284818	0.528513	0.044608	0.019*
C15	0.4114 (5)	0.56490 (15)	0.1478 (2)	0.0127 (8)
C1	0.4138 (5)	0.53416 (15)	0.4028 (2)	0.0146 (8)
H1	0.427994	0.557844	0.447456	0.017*
C2	0.3361 (5)	0.49068 (16)	0.4153 (3)	0.0181 (9)
H2	0.295013	0.485214	0.467210	0.022*
C3	0.3185 (5)	0.45529 (15)	0.3522 (3)	0.0177 (9)
H3	0.269121	0.424770	0.360926	0.021*
C4	0.3740 (5)	0.46486 (15)	0.2756 (2)	0.0171 (9)
H4	0.362905	0.441262	0.230780	0.021*
C5	0.4461 (4)	0.50989 (14)	0.2664 (2)	0.0118 (8)
C16	0.7696 (5)	0.67804 (15)	0.2075 (2)	0.0142 (8)
H16	0.755458	0.652306	0.166493	0.017*
C17	0.8538 (5)	0.71946 (16)	0.1895 (2)	0.0176 (9)
H17	0.898884	0.721472	0.138081	0.021*
C18	0.8713 (5)	0.75793 (16)	0.2476 (3)	0.0188 (9)
H18	0.928272	0.786806	0.236878	0.023*
C19	0.8034 (5)	0.75320 (15)	0.3218 (2)	0.0152 (8)
H19	0.811851	0.779197	0.362252	0.018*
C20	0.7234 (4)	0.71047 (14)	0.3365 (2)	0.0113 (8)
C21	0.2662 (5)	0.64252 (15)	0.3464 (2)	0.0162 (8)
H21	0.228360	0.612872	0.318558	0.019*
C22	0.1540 (5)	0.67308 (16)	0.3730 (3)	0.0192 (9)
H22	0.042697	0.663737	0.366764	0.023*
C23	0.2053 (5)	0.71796 (16)	0.4093 (3)	0.0188 (9)
H23	0.129180	0.740390	0.426053	0.023*
C24	0.3687 (5)	0.72921 (15)	0.4203 (2)	0.0163 (9)
H24	0.407285	0.759756	0.444306	0.020*
C25	0.4759 (5)	0.69520 (14)	0.3959 (2)	0.0120 (8)
C26	0.9761 (5)	0.72691 (16)	0.5791 (3)	0.0207 (9)
H26	1.087385	0.736011	0.583817	0.025*
C27	0.9150 (6)	0.71882 (17)	0.6538 (3)	0.0244 (10)
H27	0.982144	0.721872	0.708417	0.029*
C28	0.7517 (6)	0.70605 (17)	0.6463 (3)	0.0249 (10)
H28	0.705096	0.700071	0.696331	0.030*
C29	0.6573 (5)	0.70206 (16)	0.5659 (2)	0.0200 (9)
H29	0.545079	0.693674	0.559312	0.024*
C30	0.7328 (5)	0.71082 (14)	0.4946 (2)	0.0119 (8)
Cl2	1.1042 (2)	0.60896 (5)	0.71672 (8)	0.0461 (4)
Cl3	1.30678 (17)	0.62246 (5)	0.58615 (9)	0.0424 (3)
Cl4	1.14129 (16)	0.53000 (4)	0.59932 (7)	0.0312 (3)
C31	1.1291 (6)	0.59395 (18)	0.6109 (3)	0.0276 (11)
H31	1.032515	0.606278	0.570191	0.033*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
Sb1	0.01827 (14)	0.01482 (14)	0.01267 (12)	−0.00029 (12)	0.00293 (10)	−0.00067 (11)
F1	0.0493 (18)	0.0286 (16)	0.0210 (12)	−0.0020 (13)	0.0081 (12)	0.0090 (11)
F2	0.0367 (16)	0.0175 (14)	0.0473 (16)	0.0085 (12)	0.0158 (13)	−0.0011 (12)
F3	0.0255 (14)	0.0242 (15)	0.0340 (14)	−0.0069 (12)	−0.0024 (11)	−0.0018 (11)
F4	0.0293 (15)	0.0330 (16)	0.0441 (16)	0.0110 (13)	0.0061 (13)	−0.0165 (13)
F5	0.0266 (15)	0.0394 (17)	0.0378 (15)	−0.0092 (13)	0.0028 (12)	−0.0125 (13)
F6	0.0501 (19)	0.057 (2)	0.0188 (13)	−0.0019 (17)	0.0086 (13)	0.0155 (13)
Ru1	0.00651 (14)	0.00916 (15)	0.00999 (13)	−0.00014 (12)	0.00161 (11)	−0.00153 (12)
Cl1	0.0134 (4)	0.0141 (5)	0.0128 (4)	−0.0008 (4)	−0.0006 (3)	0.0000 (3)
N2	0.0101 (16)	0.0118 (16)	0.0107 (14)	−0.0015 (13)	0.0034 (13)	−0.0018 (13)
N3	0.0066 (15)	0.0152 (16)	0.0132 (14)	−0.0016 (13)	0.0030 (12)	0.0003 (13)
N1	0.0103 (16)	0.0102 (17)	0.0133 (15)	0.0011 (13)	0.0017 (13)	−0.0002 (13)
N4	0.0149 (17)	0.0120 (17)	0.0083 (14)	−0.0024 (13)	0.0041 (13)	−0.0024 (12)
N5	0.0076 (15)	0.0140 (17)	0.0129 (15)	0.0003 (13)	0.0014 (12)	0.0003 (13)
N6	0.0064 (15)	0.0145 (17)	0.0143 (15)	−0.0013 (13)	0.0022 (12)	−0.0023 (13)
N8	0.0094 (16)	0.0141 (17)	0.0143 (15)	−0.0029 (13)	0.0044 (13)	−0.0040 (13)
N7	0.0153 (18)	0.0180 (19)	0.0198 (17)	−0.0028 (15)	0.0023 (14)	−0.0025 (15)
C6	0.0103 (19)	0.013 (2)	0.0185 (19)	−0.0008 (16)	0.0010 (16)	−0.0029 (16)
C7	0.010 (2)	0.023 (2)	0.024 (2)	0.0020 (17)	0.0073 (17)	0.0005 (18)
C8	0.018 (2)	0.019 (2)	0.019 (2)	0.0042 (17)	0.0066 (17)	−0.0036 (17)
C9	0.018 (2)	0.014 (2)	0.0144 (18)	0.0000 (16)	0.0035 (16)	−0.0029 (16)
C10	0.014 (2)	0.0108 (19)	0.0108 (17)	0.0016 (15)	0.0032 (15)	0.0027 (15)
C11	0.014 (2)	0.015 (2)	0.0193 (19)	−0.0022 (17)	0.0040 (16)	−0.0049 (17)
C12	0.016 (2)	0.019 (2)	0.0185 (19)	0.0048 (17)	−0.0023 (16)	0.0052 (17)
C13	0.018 (2)	0.032 (3)	0.0136 (18)	0.0021 (19)	−0.0008 (16)	0.0024 (18)
C14	0.016 (2)	0.017 (2)	0.0149 (19)	0.0006 (17)	0.0040 (17)	−0.0042 (16)
C15	0.0108 (19)	0.015 (2)	0.0141 (18)	−0.0010 (16)	0.0055 (15)	0.0000 (15)
C1	0.014 (2)	0.019 (2)	0.0109 (17)	0.0005 (16)	0.0040 (15)	−0.0046 (16)
C2	0.018 (2)	0.022 (2)	0.0164 (19)	−0.0009 (18)	0.0063 (17)	0.0022 (17)
C3	0.021 (2)	0.010 (2)	0.023 (2)	−0.0041 (17)	0.0049 (17)	0.0034 (17)
C4	0.020 (2)	0.015 (2)	0.0172 (19)	−0.0013 (17)	0.0048 (17)	−0.0045 (16)
C5	0.0060 (18)	0.016 (2)	0.0129 (17)	0.0031 (15)	−0.0002 (14)	0.0009 (15)
C16	0.0115 (19)	0.016 (2)	0.0142 (18)	0.0013 (16)	−0.0007 (15)	0.0003 (16)
C17	0.016 (2)	0.023 (2)	0.0141 (18)	−0.0013 (17)	0.0035 (16)	0.0016 (17)
C18	0.019 (2)	0.017 (2)	0.021 (2)	−0.0051 (17)	0.0018 (17)	0.0058 (17)
C19	0.013 (2)	0.015 (2)	0.0168 (19)	0.0014 (16)	−0.0001 (16)	0.0000 (16)
C20	0.0064 (18)	0.013 (2)	0.0144 (17)	0.0042 (15)	0.0025 (15)	0.0004 (15)
C21	0.014 (2)	0.014 (2)	0.0209 (19)	−0.0025 (16)	0.0019 (16)	−0.0063 (16)
C22	0.0068 (19)	0.024 (2)	0.027 (2)	−0.0014 (17)	0.0044 (17)	−0.0047 (18)
C23	0.016 (2)	0.019 (2)	0.022 (2)	0.0045 (17)	0.0062 (17)	−0.0069 (18)
C24	0.015 (2)	0.015 (2)	0.0184 (19)	0.0000 (16)	0.0013 (16)	−0.0079 (16)
C25	0.0099 (18)	0.013 (2)	0.0134 (17)	−0.0002 (15)	0.0024 (15)	−0.0005 (15)
C26	0.015 (2)	0.024 (2)	0.022 (2)	−0.0043 (18)	−0.0009 (17)	−0.0065 (18)
C27	0.027 (3)	0.024 (2)	0.019 (2)	0.005 (2)	−0.0061 (19)	−0.0041 (18)
C28	0.027 (3)	0.033 (3)	0.016 (2)	0.005 (2)	0.0080 (19)	0.0019 (19)
C29	0.016 (2)	0.028 (3)	0.017 (2)	−0.0038 (18)	0.0048 (17)	−0.0018 (18)
C30	0.0141 (19)	0.0086 (19)	0.0128 (17)	0.0006 (15)	0.0013 (15)	−0.0034 (15)
Cl2	0.0788 (11)	0.0278 (7)	0.0356 (6)	0.0110 (7)	0.0209 (7)	0.0019 (6)
Cl3	0.0421 (8)	0.0379 (8)	0.0484 (7)	−0.0087 (6)	0.0115 (6)	0.0051 (6)
Cl4	0.0390 (7)	0.0251 (6)	0.0300 (6)	−0.0012 (5)	0.0076 (5)	−0.0012 (5)
C31	0.024 (2)	0.028 (3)	0.030 (2)	0.002 (2)	0.003 (2)	0.005 (2)

Geometric parameters (Å, º)

Sb1—F1	1.870 (2)	C12—C13	1.393 (6)
Sb1—F2	1.877 (3)	C13—H13	0.9500
Sb1—F3	1.884 (2)	C13—C14	1.383 (6)
Sb1—F4	1.874 (3)	C14—H14	0.9500
Sb1—F5	1.867 (3)	C14—C15	1.389 (5)
Sb1—F6	1.876 (3)	C1—H1	0.9500
Ru1—Cl1	2.4269 (9)	C1—C2	1.382 (6)
Ru1—N2	2.065 (3)	C2—H2	0.9500
Ru1—N3	2.046 (3)	C2—C3	1.379 (6)
Ru1—N1	2.057 (3)	C3—H3	0.9500
Ru1—N5	2.090 (3)	C3—C4	1.388 (6)
Ru1—N6	2.077 (3)	C4—H4	0.9500
N2—C6	1.350 (5)	C4—C5	1.387 (6)
N2—C10	1.351 (5)	C16—H16	0.9500
N3—C11	1.352 (5)	C16—C17	1.385 (6)
N3—C15	1.358 (5)	C17—H17	0.9500
N1—C1	1.351 (5)	C17—C18	1.387 (6)
N1—C5	1.354 (5)	C18—H18	0.9500
N4—C10	1.439 (5)	C18—C19	1.388 (6)
N4—C15	1.442 (5)	C19—H19	0.9500
N4—C5	1.444 (5)	C19—C20	1.382 (5)
N5—C16	1.357 (5)	C21—H21	0.9500
N5—C20	1.355 (5)	C21—C22	1.369 (6)
N6—C21	1.352 (5)	C22—H22	0.9500
N6—C25	1.354 (5)	C22—C23	1.390 (6)
N8—C20	1.423 (5)	C23—H23	0.9500
N8—C25	1.425 (5)	C23—C24	1.376 (6)
N8—C30	1.417 (5)	C24—H24	0.9500
N7—C26	1.341 (5)	C24—C25	1.387 (5)
N7—C30	1.325 (5)	C26—H26	0.9500
C6—H6	0.9500	C26—C27	1.377 (6)
C6—C7	1.378 (6)	C27—H27	0.9500
C7—H7	0.9500	C27—C28	1.389 (7)
C7—C8	1.384 (6)	C28—H28	0.9500
C8—H8	0.9500	C28—C29	1.382 (6)
C8—C9	1.393 (6)	C29—H29	0.9500
C9—H9	0.9500	C29—C30	1.398 (5)
C9—C10	1.379 (5)	Cl2—C31	1.765 (5)
C11—H11	0.9500	Cl3—C31	1.771 (5)
C11—C12	1.383 (5)	Cl4—C31	1.761 (5)
C12—H12	0.9500	C31—H31	1.0000
F1—Sb1—F2	89.87 (12)	C14—C13—C12	119.4 (4)
F1—Sb1—F3	89.53 (12)	C14—C13—H13	120.3
F1—Sb1—F4	90.06 (13)	C13—C14—H14	120.8
F1—Sb1—F6	179.44 (13)	C13—C14—C15	118.4 (4)
F2—Sb1—F3	89.04 (12)	C15—C14—H14	120.8
F4—Sb1—F2	178.69 (13)	N3—C15—N4	117.8 (3)
F4—Sb1—F3	89.66 (12)	N3—C15—C14	122.9 (4)
F4—Sb1—F6	90.24 (14)	C14—C15—N4	119.2 (3)
F5—Sb1—F1	90.47 (13)	N1—C1—H1	118.8
F5—Sb1—F2	90.42 (13)	N1—C1—C2	122.4 (4)
F5—Sb1—F3	179.46 (13)	C2—C1—H1	118.8
F5—Sb1—F4	90.88 (13)	C1—C2—H2	120.2
F5—Sb1—F6	90.00 (13)	C3—C2—C1	119.6 (4)
F6—Sb1—F2	89.82 (13)	C3—C2—H2	120.2
F6—Sb1—F3	89.99 (13)	C2—C3—H3	120.4
N2—Ru1—Cl1	88.41 (9)	C2—C3—C4	119.1 (4)
N2—Ru1—N5	94.29 (12)	C4—C3—H3	120.4
N2—Ru1—N6	177.10 (12)	C3—C4—H4	121.0
N3—Ru1—Cl1	173.96 (10)	C5—C4—C3	118.0 (4)
N3—Ru1—N2	86.69 (12)	C5—C4—H4	121.0
N3—Ru1—N1	85.98 (12)	N1—C5—N4	116.5 (3)
N3—Ru1—N5	93.11 (12)	N1—C5—C4	123.5 (3)
N3—Ru1—N6	90.41 (12)	C4—C5—N4	120.0 (3)
N1—Ru1—Cl1	90.16 (9)	N5—C16—H16	118.3
N1—Ru1—N2	86.14 (12)	N5—C16—C17	123.4 (4)
N1—Ru1—N5	178.97 (12)	C17—C16—H16	118.3
N1—Ru1—N6	93.53 (13)	C16—C17—H17	120.5
N5—Ru1—Cl1	90.79 (8)	C16—C17—C18	119.0 (4)
N6—Ru1—Cl1	94.47 (8)	C18—C17—H17	120.5
N6—Ru1—N5	85.99 (13)	C17—C18—H18	120.8
C6—N2—Ru1	124.7 (3)	C17—C18—C19	118.4 (4)
C6—N2—C10	117.8 (3)	C19—C18—H18	120.8
C10—N2—Ru1	117.5 (3)	C18—C19—H19	120.2
C11—N3—Ru1	125.3 (3)	C20—C19—C18	119.6 (4)
C11—N3—C15	117.6 (3)	C20—C19—H19	120.2
C15—N3—Ru1	117.0 (3)	N5—C20—N8	116.5 (3)
C1—N1—Ru1	124.8 (3)	N5—C20—C19	122.9 (4)
C1—N1—C5	117.2 (3)	C19—C20—N8	120.5 (3)
C5—N1—Ru1	118.0 (3)	N6—C21—H21	118.1
C10—N4—C15	113.0 (3)	N6—C21—C22	123.8 (4)
C10—N4—C5	111.8 (3)	C22—C21—H21	118.1
C15—N4—C5	111.2 (3)	C21—C22—H22	120.5
C16—N5—Ru1	121.2 (3)	C21—C22—C23	119.1 (4)
C20—N5—Ru1	122.0 (2)	C23—C22—H22	120.5
C20—N5—C16	116.7 (3)	C22—C23—H23	120.7
C21—N6—Ru1	122.0 (3)	C24—C23—C22	118.6 (4)
C21—N6—C25	116.1 (3)	C24—C23—H23	120.7
C25—N6—Ru1	121.5 (3)	C23—C24—H24	120.6
C20—N8—C25	117.7 (3)	C23—C24—C25	118.9 (4)
C30—N8—C20	122.1 (3)	C25—C24—H24	120.6
C30—N8—C25	120.3 (3)	N6—C25—N8	117.3 (3)
C30—N7—C26	117.0 (4)	N6—C25—C24	123.4 (4)
N2—C6—H6	119.1	C24—C25—N8	119.2 (3)
N2—C6—C7	121.8 (4)	N7—C26—H26	117.9
C7—C6—H6	119.1	N7—C26—C27	124.3 (4)
C6—C7—H7	119.8	C27—C26—H26	117.9
C6—C7—C8	120.5 (4)	C26—C27—H27	121.2
C8—C7—H7	119.8	C26—C27—C28	117.5 (4)
C7—C8—H8	121.0	C28—C27—H27	121.2
C7—C8—C9	118.0 (4)	C27—C28—H28	120.1
C9—C8—H8	121.0	C29—C28—C27	119.8 (4)
C8—C9—H9	120.6	C29—C28—H28	120.1
C10—C9—C8	118.8 (4)	C28—C29—H29	121.2
C10—C9—H9	120.6	C28—C29—C30	117.6 (4)
N2—C10—N4	117.1 (3)	C30—C29—H29	121.2
N2—C10—C9	123.2 (4)	N7—C30—N8	115.1 (3)
C9—C10—N4	119.7 (3)	N7—C30—C29	123.8 (3)
N3—C11—H11	118.7	C29—C30—N8	121.0 (3)
N3—C11—C12	122.7 (4)	Cl2—C31—Cl3	109.9 (3)
C12—C11—H11	118.7	Cl2—C31—H31	108.8
C11—C12—H12	120.6	Cl3—C31—H31	108.8
C11—C12—C13	118.9 (4)	Cl4—C31—Cl2	110.3 (3)
C13—C12—H12	120.6	Cl4—C31—Cl3	110.4 (3)
C12—C13—H13	120.3	Cl4—C31—H31	108.8
Ru1—N2—C6—C7	−178.1 (3)	C1—N1—C5—C4	−3.0 (5)
Ru1—N2—C10—N4	−2.2 (4)	C1—C2—C3—C4	−2.4 (6)
Ru1—N2—C10—C9	179.2 (3)	C2—C3—C4—C5	0.4 (6)
Ru1—N3—C11—C12	−175.0 (3)	C3—C4—C5—N1	2.4 (6)
Ru1—N3—C15—N4	−3.9 (4)	C3—C4—C5—N4	−176.7 (3)
Ru1—N3—C15—C14	174.8 (3)	C5—N1—C1—C2	0.8 (6)
Ru1—N1—C1—C2	−179.3 (3)	C5—N4—C10—N2	−62.6 (4)
Ru1—N1—C5—N4	−3.8 (4)	C5—N4—C10—C9	116.0 (4)
Ru1—N1—C5—C4	177.1 (3)	C5—N4—C15—N3	66.4 (4)
Ru1—N5—C16—C17	−177.4 (3)	C5—N4—C15—C14	−112.4 (4)
Ru1—N5—C20—N8	−5.0 (4)	C16—N5—C20—N8	175.2 (3)
Ru1—N5—C20—C19	178.6 (3)	C16—N5—C20—C19	−1.2 (5)
Ru1—N6—C21—C22	−174.3 (3)	C16—C17—C18—C19	0.1 (6)
Ru1—N6—C25—N8	−8.2 (5)	C17—C18—C19—C20	1.1 (6)
Ru1—N6—C25—C24	170.7 (3)	C18—C19—C20—N5	−0.5 (6)
N2—C6—C7—C8	−1.0 (6)	C18—C19—C20—N8	−176.8 (3)
N3—C11—C12—C13	0.1 (6)	C20—N5—C16—C17	2.4 (5)
N1—C1—C2—C3	1.8 (6)	C20—N8—C25—N6	62.8 (5)
N5—C16—C17—C18	−1.9 (6)	C20—N8—C25—C24	−116.1 (4)
N6—C21—C22—C23	3.8 (6)	C20—N8—C30—N7	3.6 (5)
N7—C26—C27—C28	−0.7 (7)	C20—N8—C30—C29	−174.6 (4)
C6—N2—C10—N4	178.5 (3)	C21—N6—C25—N8	178.8 (3)
C6—N2—C10—C9	−0.1 (5)	C21—N6—C25—C24	−2.4 (6)
C6—C7—C8—C9	−0.2 (6)	C21—C22—C23—C24	−2.6 (6)
C7—C8—C9—C10	1.2 (6)	C22—C23—C24—C25	−0.8 (6)
C8—C9—C10—N2	−1.1 (6)	C23—C24—C25—N6	3.4 (6)
C8—C9—C10—N4	−179.6 (3)	C23—C24—C25—N8	−177.8 (4)
C10—N2—C6—C7	1.1 (6)	C25—N6—C21—C22	−1.3 (6)
C10—N4—C15—N3	−60.3 (4)	C25—N8—C20—N5	−54.6 (5)
C10—N4—C15—C14	120.9 (4)	C25—N8—C20—C19	121.9 (4)
C10—N4—C5—N1	66.4 (4)	C25—N8—C30—N7	−177.2 (4)
C10—N4—C5—C4	−114.5 (4)	C25—N8—C30—C29	4.6 (6)
C11—N3—C15—N4	179.4 (3)	C26—N7—C30—N8	−178.7 (4)
C11—N3—C15—C14	−1.9 (6)	C26—N7—C30—C29	−0.6 (6)
C11—C12—C13—C14	−1.2 (6)	C26—C27—C28—C29	−0.2 (7)
C12—C13—C14—C15	0.8 (6)	C27—C28—C29—C30	0.6 (7)
C13—C14—C15—N3	0.8 (6)	C28—C29—C30—N8	177.8 (4)
C13—C14—C15—N4	179.6 (4)	C28—C29—C30—N7	−0.2 (7)
C15—N3—C11—C12	1.4 (6)	C30—N8—C20—N5	124.6 (4)
C15—N4—C10—N2	63.7 (4)	C30—N8—C20—C19	−58.9 (5)
C15—N4—C10—C9	−117.6 (4)	C30—N8—C25—N6	−116.4 (4)
C15—N4—C5—N1	−60.9 (4)	C30—N8—C25—C24	64.7 (5)
C15—N4—C5—C4	118.2 (4)	C30—N7—C26—C27	1.1 (7)
C1—N1—C5—N4	176.1 (3)