Dichlorido(furfuryl-amine-κN)(η-hexa-methyl-benzene)-ruthenium(II).

The single-crystal X-ray structure analysis of [RuCl(2)(C(12)H(18))(C(5)H(7)NO)] reveals a distorted piano-stool geometry around the Ru(II) atom, with a hexa-methyl-benzene ligand, two chloride ligands and a furfuryl-amine ligand, the latter coordinating through the amine group. In the crystal, a dimeric structure is observed as a result of N-H⋯Cl inter-actions between two symmetry-related mol-ecules.

Related literature

For publications dealing with metal complexes of furfuryl­amine derivatives, see: Hu et al. (2006 ▶); Joesten et al. (1967 ▶). For reviews on arene–ruthenium complexes as anti­cancer agents, see: Süss-Fink (2010 ▶); Therrien & Smith (2011 ▶). For biological activity of metal complexes of furfuryl derivatives, see: Hamann et al. (1968 ▶); Shi et al. (2008 ▶). For a review on arene–ruthenium chemistry, see: Therrien (2009 ▶). For the synthesis, see: Bennett et al. (1982 ▶). For related structures, see: Govindaswamy et al. (2004 ▶); Therrien & Süss-Fink (2004 ▶); Therrien et al. (2004 ▶).

Experimental

Crystal data

[RuCl2(C12H18)(C5H7NO)]

M = 431.35

Monoclinic,

a = 7.6883 (6) Å

b = 22.8748 (18) Å

c = 10.1000 (7) Å

β = 100.493 (9)°

V = 1746.6 (2) Å3

Z = 4

Mo Kα radiation

μ = 1.20 mm−1

T = 173 K

0.15 × 0.12 × 0.11 mm

Data collection

Bruker SMART CCD diffractometer

13771 measured reflections

3428 independent reflections

2693 reflections with I > 2σ(I)

R int = 0.040

Refinement

R[F 2 > 2σ(F 2)] = 0.033

wR(F 2) = 0.081

S = 0.94

3428 reflections

205 parameters

H-atom parameters constrained

Δρmax = 0.65 e Å−3

Δρmin = −0.98 e Å−3

Data collection: SMART (Bruker, 1999 ▶); cell refinement: SMART and SAINT (Bruker, 1999 ▶); data reduction: SAINT; program(s) used to solve structure: SIR97 (Altomare et al., 1999 ▶); program(s) used to refine structure: SHELXTL (Sheldrick, 2008 ▶); molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL.

Crystal structure: contains datablock(s) I, global. DOI: 10.1107/S1600536811043170/ff2034sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536811043170/ff2034Isup2.hkl

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

[RuCl2(C12H18)(C5H7NO)]	F(000) = 880
Mr = 431.35	Dx = 1.640 Mg m−3
Monoclinic, P21/a	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2yab	Cell parameters from 8000 reflections
a = 7.6883 (6) Å	θ = 2.0–26.1°
b = 22.8748 (18) Å	µ = 1.20 mm−1
c = 10.1000 (7) Å	T = 173 K
β = 100.493 (9)°	Block, orange
V = 1746.6 (2) Å3	0.15 × 0.12 × 0.11 mm
Z = 4

Bruker SMART CCD PLATFORM diffractometer	2693 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	Rint = 0.040
graphite	θmax = 26.0°, θmin = 2.1°
Detector resolution: 0 pixels mm-1	h = −9→9
ω scans	k = −28→28
13771 measured reflections	l = −12→12
3428 independent 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)] = 0.033	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.081	H-atom parameters constrained
S = 0.94	w = 1/[σ2(Fo2) + (0.0567P)2] where P = (Fo2 + 2Fc2)/3
3428 reflections	(Δ/σ)max = 0.002
205 parameters	Δρmax = 0.65 e Å−3
0 restraints	Δρmin = −0.98 e Å−3

Experimental. A crystal was mounted at 173 K on a Bruker SMART CCD PLATFORM using Mo Kα graphite monochromated radiation. Image plate distance 70 mm, φ oscillation scans 0 - 200°, step Δφ = 1.0°, 3 minutes per frame.

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
C1	−0.2917 (6)	0.67556 (18)	−0.3554 (4)	0.0458 (11)
H1	−0.3165	0.6690	−0.4478	0.055*
C2	−0.3965 (6)	0.7033 (2)	−0.2866 (5)	0.0554 (14)
H2	−0.5055	0.7201	−0.3215	0.067*
C3	−0.3115 (6)	0.70300 (18)	−0.1486 (4)	0.0416 (10)
H3	−0.3544	0.7188	−0.0760	0.050*
C4	−0.1575 (5)	0.67527 (14)	−0.1450 (3)	0.0258 (7)
C5	−0.0108 (5)	0.66154 (16)	−0.0330 (4)	0.0318 (8)
H5A	0.0999	0.6643	−0.0657	0.038*
H5B	−0.0086	0.6908	0.0368	0.038*
C6	0.3433 (4)	0.64157 (14)	0.2398 (3)	0.0189 (7)
C7	0.3751 (4)	0.58374 (14)	0.1941 (3)	0.0204 (7)
C8	0.3450 (4)	0.53442 (14)	0.2709 (3)	0.0194 (7)
C9	0.2821 (4)	0.54158 (14)	0.3960 (3)	0.0200 (7)
C10	0.2485 (4)	0.59829 (14)	0.4412 (3)	0.0190 (7)
C11	0.2777 (4)	0.64832 (14)	0.3620 (3)	0.0194 (7)
C12	0.3872 (5)	0.69403 (15)	0.1635 (4)	0.0276 (8)
H12A	0.3169	0.7266	0.1823	0.041*
H12B	0.3624	0.6858	0.0687	0.041*
H12C	0.5103	0.7033	0.1906	0.041*
C13	0.4423 (5)	0.57521 (16)	0.0645 (3)	0.0281 (8)
H13A	0.5586	0.5584	0.0834	0.042*
H13B	0.4469	0.6123	0.0207	0.042*
H13C	0.3641	0.5495	0.0066	0.042*
C14	0.3796 (5)	0.47449 (15)	0.2214 (4)	0.0324 (8)
H14A	0.3347	0.4720	0.1264	0.049*
H14B	0.3218	0.4459	0.2678	0.049*
H14C	0.5047	0.4672	0.2382	0.049*
C15	0.2467 (5)	0.48765 (15)	0.4726 (3)	0.0277 (8)
H15A	0.1908	0.4986	0.5465	0.042*
H15B	0.3564	0.4682	0.5063	0.042*
H15C	0.1703	0.4618	0.4136	0.042*
C16	0.1769 (5)	0.60788 (16)	0.5680 (3)	0.0291 (8)
H16A	0.1548	0.5708	0.6062	0.044*
H16B	0.0684	0.6296	0.5477	0.044*
H16C	0.2615	0.6294	0.6312	0.044*
C17	0.2342 (5)	0.70814 (14)	0.4072 (3)	0.0284 (8)
H17A	0.3356	0.7331	0.4119	0.043*
H17B	0.2020	0.7056	0.4945	0.043*
H17C	0.1373	0.7241	0.3441	0.043*
Cl1	−0.15438 (11)	0.63943 (4)	0.27606 (9)	0.0297 (2)
Cl2	−0.08251 (10)	0.50113 (3)	0.18615 (8)	0.02257 (18)
N	−0.0221 (4)	0.60308 (11)	0.0272 (3)	0.0209 (6)
H1A	0.0225	0.5772	−0.0248	0.025*
H1B	−0.1376	0.5945	0.0208	0.025*
O	−0.1412 (4)	0.65784 (12)	−0.2709 (2)	0.0377 (6)
Ru	0.10420 (3)	0.587116 (10)	0.23267 (2)	0.01582 (9)

	U11	U22	U33	U12	U13	U23
C1	0.071 (3)	0.032 (2)	0.0259 (19)	−0.008 (2)	−0.013 (2)	0.0090 (17)
C2	0.049 (3)	0.044 (3)	0.059 (3)	0.006 (2)	−0.027 (2)	0.011 (2)
C3	0.041 (2)	0.037 (2)	0.044 (2)	0.0089 (19)	0.0012 (19)	−0.0058 (18)
C4	0.0314 (19)	0.0203 (16)	0.0236 (16)	−0.0037 (15)	−0.0008 (14)	0.0029 (13)
C5	0.035 (2)	0.0264 (19)	0.0295 (18)	−0.0074 (16)	−0.0050 (15)	0.0062 (15)
C6	0.0107 (15)	0.0185 (15)	0.0259 (16)	−0.0042 (12)	−0.0011 (12)	−0.0005 (12)
C7	0.0136 (15)	0.0233 (16)	0.0241 (16)	−0.0020 (13)	0.0031 (12)	−0.0033 (13)
C8	0.0126 (15)	0.0195 (16)	0.0249 (16)	0.0029 (12)	0.0004 (12)	−0.0005 (13)
C9	0.0147 (16)	0.0207 (16)	0.0223 (15)	0.0001 (13)	−0.0027 (12)	0.0038 (12)
C10	0.0157 (15)	0.0257 (17)	0.0140 (14)	−0.0015 (13)	−0.0018 (12)	−0.0026 (12)
C11	0.0156 (16)	0.0200 (16)	0.0199 (15)	−0.0032 (13)	−0.0039 (12)	−0.0055 (12)
C12	0.0248 (18)	0.0246 (17)	0.0329 (18)	−0.0080 (15)	0.0039 (14)	0.0020 (14)
C13	0.0269 (18)	0.033 (2)	0.0263 (17)	−0.0018 (15)	0.0114 (14)	−0.0063 (14)
C14	0.031 (2)	0.0235 (18)	0.044 (2)	0.0068 (16)	0.0093 (17)	−0.0049 (15)
C15	0.0280 (19)	0.0251 (17)	0.0291 (18)	0.0007 (15)	0.0024 (15)	0.0070 (14)
C16	0.035 (2)	0.0317 (19)	0.0218 (16)	−0.0043 (16)	0.0071 (15)	−0.0031 (14)
C17	0.036 (2)	0.0207 (17)	0.0280 (17)	−0.0007 (15)	0.0035 (15)	−0.0072 (14)
Cl1	0.0201 (4)	0.0318 (5)	0.0365 (5)	0.0070 (4)	0.0036 (3)	−0.0094 (4)
Cl2	0.0227 (4)	0.0208 (4)	0.0239 (4)	−0.0054 (3)	0.0035 (3)	−0.0013 (3)
N	0.0230 (14)	0.0196 (14)	0.0188 (13)	0.0006 (11)	−0.0003 (11)	0.0025 (10)
O	0.0504 (17)	0.0359 (15)	0.0274 (13)	−0.0006 (13)	0.0083 (12)	0.0029 (11)
Ru	0.01421 (14)	0.01550 (14)	0.01747 (14)	0.00002 (10)	0.00214 (9)	−0.00114 (10)

C1—C2	1.319 (7)	C10—Ru	2.209 (3)
C1—O	1.368 (5)	C11—C17	1.499 (4)
C1—H1	0.9300	C11—Ru	2.194 (3)
C2—C3	1.428 (6)	C12—H12A	0.9600
C2—H2	0.9300	C12—H12B	0.9600
C3—C4	1.338 (5)	C12—H12C	0.9600
C3—H3	0.9300	C13—H13A	0.9600
C4—O	1.360 (4)	C13—H13B	0.9600
C4—C5	1.478 (5)	C13—H13C	0.9600
C5—N	1.478 (4)	C14—H14A	0.9600
C5—H5A	0.9700	C14—H14B	0.9600
C5—H5B	0.9700	C14—H14C	0.9600
C6—C11	1.425 (4)	C15—H15A	0.9600
C6—C7	1.437 (4)	C15—H15B	0.9600
C6—C12	1.498 (4)	C15—H15C	0.9600
C6—Ru	2.211 (3)	C16—H16A	0.9600
C7—C8	1.412 (4)	C16—H16B	0.9600
C7—C13	1.505 (5)	C16—H16C	0.9600
C7—Ru	2.189 (3)	C17—H17A	0.9600
C8—C9	1.442 (4)	C17—H17B	0.9600
C8—C14	1.500 (4)	C17—H17C	0.9600
C8—Ru	2.184 (3)	Cl1—Ru	2.4277 (9)
C9—C10	1.415 (4)	Cl2—Ru	2.4299 (8)
C9—C15	1.507 (4)	N—Ru	2.156 (2)
C9—Ru	2.204 (3)	N—H1A	0.9000
C10—C11	1.437 (4)	N—H1B	0.9000
C10—C16	1.499 (4)
C2—C1—O	110.0 (3)	C8—C14—H14B	109.5
C2—C1—H1	125.0	H14A—C14—H14B	109.5
O—C1—H1	125.0	C8—C14—H14C	109.5
C1—C2—C3	107.3 (4)	H14A—C14—H14C	109.5
C1—C2—H2	126.4	H14B—C14—H14C	109.5
C3—C2—H2	126.4	C9—C15—H15A	109.5
C4—C3—C2	105.9 (4)	C9—C15—H15B	109.5
C4—C3—H3	127.0	H15A—C15—H15B	109.5
C2—C3—H3	127.0	C9—C15—H15C	109.5
C3—C4—O	110.2 (3)	H15A—C15—H15C	109.5
C3—C4—C5	132.0 (4)	H15B—C15—H15C	109.5
O—C4—C5	117.8 (3)	C10—C16—H16A	109.5
N—C5—C4	114.4 (3)	C10—C16—H16B	109.5
N—C5—H5A	108.7	H16A—C16—H16B	109.5
C4—C5—H5A	108.7	C10—C16—H16C	109.5
N—C5—H5B	108.7	H16A—C16—H16C	109.5
C4—C5—H5B	108.7	H16B—C16—H16C	109.5
H5A—C5—H5B	107.6	C11—C17—H17A	109.5
C11—C6—C7	119.1 (3)	C11—C17—H17B	109.5
C11—C6—C12	120.5 (3)	H17A—C17—H17B	109.5
C7—C6—C12	120.3 (3)	C11—C17—H17C	109.5
C11—C6—Ru	70.48 (17)	H17A—C17—H17C	109.5
C7—C6—Ru	70.13 (17)	H17B—C17—H17C	109.5
C12—C6—Ru	134.3 (2)	C5—N—Ru	119.9 (2)
C8—C7—C6	120.3 (3)	C5—N—H1A	107.3
C8—C7—C13	119.4 (3)	Ru—N—H1A	107.3
C6—C7—C13	120.3 (3)	C5—N—H1B	107.3
C8—C7—Ru	70.96 (18)	Ru—N—H1B	107.3
C6—C7—Ru	71.76 (18)	H1A—N—H1B	106.9
C13—C7—Ru	130.4 (2)	C4—O—C1	106.6 (3)
C7—C8—C9	120.4 (3)	N—Ru—C8	118.85 (11)
C7—C8—C14	119.3 (3)	N—Ru—C7	96.38 (11)
C9—C8—C14	120.3 (3)	C8—Ru—C7	37.68 (12)
C7—C8—Ru	71.36 (18)	N—Ru—C11	125.70 (11)
C9—C8—Ru	71.56 (17)	C8—Ru—C11	80.97 (12)
C14—C8—Ru	129.9 (2)	C7—Ru—C11	68.50 (12)
C10—C9—C8	119.8 (3)	N—Ru—C9	155.51 (12)
C10—C9—C15	121.6 (3)	C8—Ru—C9	38.38 (12)
C8—C9—C15	118.5 (3)	C7—Ru—C9	68.63 (12)
C10—C9—Ru	71.52 (17)	C11—Ru—C9	68.20 (12)
C8—C9—Ru	70.07 (17)	N—Ru—C10	163.32 (11)
C15—C9—Ru	128.7 (2)	C8—Ru—C10	68.47 (11)
C9—C10—C11	119.6 (3)	C7—Ru—C10	81.08 (12)
C9—C10—C16	121.8 (3)	C11—Ru—C10	38.10 (11)
C11—C10—C16	118.5 (3)	C9—Ru—C10	37.40 (11)
C9—C10—Ru	71.08 (16)	N—Ru—C6	99.31 (11)
C11—C10—Ru	70.36 (16)	C8—Ru—C6	68.43 (12)
C16—C10—Ru	129.2 (2)	C7—Ru—C6	38.11 (11)
C6—C11—C10	120.8 (3)	C11—Ru—C6	37.75 (12)
C6—C11—C17	119.7 (3)	C9—Ru—C6	80.98 (12)
C10—C11—C17	119.4 (3)	C10—Ru—C6	68.52 (12)
C6—C11—Ru	71.77 (17)	N—Ru—Cl1	81.39 (8)
C10—C11—Ru	71.54 (17)	C8—Ru—Cl1	159.36 (9)
C17—C11—Ru	128.2 (2)	C7—Ru—Cl1	152.45 (9)
C6—C12—H12A	109.5	C11—Ru—Cl1	90.40 (9)
C6—C12—H12B	109.5	C9—Ru—Cl1	120.98 (9)
H12A—C12—H12B	109.5	C10—Ru—Cl1	93.22 (9)
C6—C12—H12C	109.5	C6—Ru—Cl1	114.82 (9)
H12A—C12—H12C	109.5	N—Ru—Cl2	78.72 (7)
H12B—C12—H12C	109.5	C8—Ru—Cl2	92.25 (8)
C7—C13—H13A	109.5	C7—Ru—Cl2	119.00 (8)
C7—C13—H13B	109.5	C11—Ru—Cl2	154.90 (9)
H13A—C13—H13B	109.5	C9—Ru—Cl2	91.51 (8)
C7—C13—H13C	109.5	C10—Ru—Cl2	117.02 (9)
H13A—C13—H13C	109.5	C6—Ru—Cl2	157.04 (9)
H13B—C13—H13C	109.5	Cl1—Ru—Cl2	87.68 (3)
C8—C14—H14A	109.5
O—C1—C2—C3	−1.1 (5)	C8—C7—Ru—C10	66.14 (18)
C1—C2—C3—C4	1.0 (5)	C6—C7—Ru—C10	−66.39 (18)
C2—C3—C4—O	−0.6 (5)	C13—C7—Ru—C10	179.0 (3)
C2—C3—C4—C5	179.2 (4)	C8—C7—Ru—C6	132.5 (3)
C3—C4—C5—N	93.9 (5)	C13—C7—Ru—C6	−114.6 (4)
O—C4—C5—N	−86.4 (4)	C8—C7—Ru—Cl1	145.91 (17)
C11—C6—C7—C8	−1.2 (4)	C6—C7—Ru—Cl1	13.4 (3)
C12—C6—C7—C8	175.7 (3)	C13—C7—Ru—Cl1	−101.2 (3)
Ru—C6—C7—C8	−53.8 (3)	C8—C7—Ru—Cl2	−49.89 (19)
C11—C6—C7—C13	179.3 (3)	C6—C7—Ru—Cl2	177.58 (14)
C12—C6—C7—C13	−3.8 (4)	C13—C7—Ru—Cl2	63.0 (3)
Ru—C6—C7—C13	126.7 (3)	C6—C11—Ru—N	−52.9 (2)
C11—C6—C7—Ru	52.6 (2)	C10—C11—Ru—N	174.38 (17)
C12—C6—C7—Ru	−130.5 (3)	C17—C11—Ru—N	61.0 (3)
C6—C7—C8—C9	−0.1 (5)	C6—C11—Ru—C8	66.24 (19)
C13—C7—C8—C9	179.5 (3)	C10—C11—Ru—C8	−66.45 (19)
Ru—C7—C8—C9	−54.2 (3)	C17—C11—Ru—C8	−179.8 (3)
C6—C7—C8—C14	−179.8 (3)	C6—C11—Ru—C7	29.25 (18)
C13—C7—C8—C14	−0.3 (4)	C10—C11—Ru—C7	−103.4 (2)
Ru—C7—C8—C14	126.0 (3)	C17—C11—Ru—C7	143.2 (3)
C6—C7—C8—Ru	54.2 (3)	C6—C11—Ru—C9	103.9 (2)
C13—C7—C8—Ru	−126.3 (3)	C10—C11—Ru—C9	−28.76 (18)
C7—C8—C9—C10	0.7 (4)	C17—C11—Ru—C9	−142.1 (3)
C14—C8—C9—C10	−179.5 (3)	C6—C11—Ru—C10	132.7 (3)
Ru—C8—C9—C10	−53.4 (2)	C17—C11—Ru—C10	−113.4 (4)
C7—C8—C9—C15	178.2 (3)	C10—C11—Ru—C6	−132.7 (3)
C14—C8—C9—C15	−2.0 (4)	C17—C11—Ru—C6	113.9 (4)
Ru—C8—C9—C15	124.1 (3)	C6—C11—Ru—Cl1	−132.59 (17)
C7—C8—C9—Ru	54.1 (3)	C10—C11—Ru—Cl1	94.72 (17)
C14—C8—C9—Ru	−126.1 (3)	C17—C11—Ru—Cl1	−18.7 (3)
C8—C9—C10—C11	−0.1 (4)	C6—C11—Ru—Cl2	142.04 (19)
C15—C9—C10—C11	−177.5 (3)	C10—C11—Ru—Cl2	9.3 (3)
Ru—C9—C10—C11	−52.9 (2)	C17—C11—Ru—Cl2	−104.0 (3)
C8—C9—C10—C16	177.8 (3)	C10—C9—Ru—N	158.9 (2)
C15—C9—C10—C16	0.4 (5)	C8—C9—Ru—N	26.2 (3)
Ru—C9—C10—C16	125.1 (3)	C15—C9—Ru—N	−84.9 (4)
C8—C9—C10—Ru	52.7 (2)	C10—C9—Ru—C8	132.7 (3)
C15—C9—C10—Ru	−124.7 (3)	C15—C9—Ru—C8	−111.1 (4)
C7—C6—C11—C10	1.8 (4)	C10—C9—Ru—C7	103.8 (2)
C12—C6—C11—C10	−175.1 (3)	C8—C9—Ru—C7	−28.97 (17)
Ru—C6—C11—C10	54.3 (3)	C15—C9—Ru—C7	−140.1 (3)
C7—C6—C11—C17	−176.6 (3)	C10—C9—Ru—C11	29.27 (18)
C12—C6—C11—C17	6.5 (4)	C8—C9—Ru—C11	−103.5 (2)
Ru—C6—C11—C17	−124.2 (3)	C15—C9—Ru—C11	145.4 (3)
C7—C6—C11—Ru	−52.4 (3)	C8—C9—Ru—C10	−132.7 (3)
C12—C6—C11—Ru	130.7 (3)	C15—C9—Ru—C10	116.2 (4)
C9—C10—C11—C6	−1.2 (4)	C10—C9—Ru—C6	66.25 (19)
C16—C10—C11—C6	−179.1 (3)	C8—C9—Ru—C6	−66.48 (19)
Ru—C10—C11—C6	−54.4 (3)	C15—C9—Ru—C6	−177.6 (3)
C9—C10—C11—C17	177.3 (3)	C10—C9—Ru—Cl1	−47.4 (2)
C16—C10—C11—C17	−0.7 (4)	C8—C9—Ru—Cl1	179.92 (15)
Ru—C10—C11—C17	124.1 (3)	C15—C9—Ru—Cl1	68.8 (3)
C9—C10—C11—Ru	53.2 (2)	C10—C9—Ru—Cl2	−135.55 (17)
C16—C10—C11—Ru	−124.8 (3)	C8—C9—Ru—Cl2	91.72 (17)
C4—C5—N—Ru	−154.7 (3)	C15—C9—Ru—Cl2	−19.4 (3)
C3—C4—O—C1	−0.1 (4)	C9—C10—Ru—N	−148.7 (4)
C5—C4—O—C1	−179.9 (3)	C11—C10—Ru—N	−16.1 (5)
C2—C1—O—C4	0.7 (5)	C16—C10—Ru—N	95.2 (5)
C5—N—Ru—C8	−106.9 (3)	C9—C10—Ru—C8	−29.36 (18)
C5—N—Ru—C7	−74.8 (3)	C11—C10—Ru—C8	103.3 (2)
C5—N—Ru—C11	−6.8 (3)	C16—C10—Ru—C8	−145.4 (3)
C5—N—Ru—C9	−125.1 (3)	C9—C10—Ru—C7	−66.30 (19)
C5—N—Ru—C10	5.4 (5)	C11—C10—Ru—C7	66.35 (19)
C5—N—Ru—C6	−36.4 (3)	C16—C10—Ru—C7	177.7 (3)
C5—N—Ru—Cl1	77.5 (3)	C9—C10—Ru—C11	−132.6 (3)
C5—N—Ru—Cl2	166.8 (3)	C16—C10—Ru—C11	111.3 (4)
C7—C8—Ru—N	59.6 (2)	C11—C10—Ru—C9	132.6 (3)
C9—C8—Ru—N	−167.94 (16)	C16—C10—Ru—C9	−116.0 (4)
C14—C8—Ru—N	−53.5 (3)	C9—C10—Ru—C6	−103.7 (2)
C9—C8—Ru—C7	132.4 (3)	C11—C10—Ru—C6	28.92 (18)
C14—C8—Ru—C7	−113.1 (4)	C16—C10—Ru—C6	140.2 (3)
C7—C8—Ru—C11	−66.33 (18)	C9—C10—Ru—Cl1	140.83 (17)
C9—C8—Ru—C11	66.11 (19)	C11—C10—Ru—Cl1	−86.53 (18)
C14—C8—Ru—C11	−179.4 (3)	C16—C10—Ru—Cl1	24.8 (3)
C7—C8—Ru—C9	−132.4 (3)	C9—C10—Ru—Cl2	51.8 (2)
C14—C8—Ru—C9	114.5 (4)	C11—C10—Ru—Cl2	−175.56 (15)
C7—C8—Ru—C10	−103.8 (2)	C16—C10—Ru—Cl2	−64.3 (3)
C9—C8—Ru—C10	28.66 (17)	C11—C6—Ru—N	138.96 (18)
C14—C8—Ru—C10	143.1 (3)	C7—C6—Ru—N	−88.47 (18)
C7—C8—Ru—C6	−29.28 (17)	C12—C6—Ru—N	25.0 (3)
C9—C8—Ru—C6	103.2 (2)	C11—C6—Ru—C8	−103.6 (2)
C14—C8—Ru—C6	−142.4 (3)	C7—C6—Ru—C8	28.97 (18)
C7—C8—Ru—Cl1	−132.6 (2)	C12—C6—Ru—C8	142.4 (4)
C9—C8—Ru—Cl1	−0.2 (4)	C11—C6—Ru—C7	−132.6 (3)
C14—C8—Ru—Cl1	114.3 (3)	C12—C6—Ru—C7	113.4 (4)
C7—C8—Ru—Cl2	137.98 (17)	C7—C6—Ru—C11	132.6 (3)
C9—C8—Ru—Cl2	−89.59 (17)	C12—C6—Ru—C11	−114.0 (4)
C14—C8—Ru—Cl2	24.9 (3)	C11—C6—Ru—C9	−65.85 (19)
C8—C7—Ru—N	−130.50 (18)	C7—C6—Ru—C9	66.72 (19)
C6—C7—Ru—N	96.97 (18)	C12—C6—Ru—C9	−179.8 (3)
C13—C7—Ru—N	−17.6 (3)	C11—C6—Ru—C10	−29.17 (18)
C6—C7—Ru—C8	−132.5 (3)	C7—C6—Ru—C10	103.4 (2)
C13—C7—Ru—C8	112.9 (4)	C12—C6—Ru—C10	−143.2 (4)
C8—C7—Ru—C11	103.5 (2)	C11—C6—Ru—Cl1	54.20 (19)
C6—C7—Ru—C11	−28.98 (18)	C7—C6—Ru—Cl1	−173.23 (15)
C13—C7—Ru—C11	−143.6 (3)	C12—C6—Ru—Cl1	−59.8 (3)
C8—C7—Ru—C9	29.47 (18)	C11—C6—Ru—Cl2	−138.00 (19)
C6—C7—Ru—C9	−103.05 (19)	C7—C6—Ru—Cl2	−5.4 (3)
C13—C7—Ru—C9	142.3 (3)	C12—C6—Ru—Cl2	108.0 (3)

D—H···A	D—H	H···A	D···A	D—H···A
N—H1A···Cl2i	0.9	2.52	3.406 (3)	168.

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N—H1A⋯Cl2i	0.9	2.52	3.406 (3)	168

Symmetry code: (i) .