Crystal structure of [3-amino-2-(phenyl-diazenyl)-pyridine]chlorido-(η(6)-p-cymene)-ruthenium(II) chloride.

The title compound, [RuCl(C10H14)(C11H10N4)]Cl is an Ru(II) complex in which an η (6) -p-cymene ligand, two N atoms of 3-amino-2-(phenyl-azo)pyridine and one Cl ion form a piano-stool coordination environment around the metal ion. In the crystal structure, N-H⋯Cl hydrogen bonds play an important role in the formation of the supramolecular zigzag chain along the a-axis direction. Disorder is observed for the isopropyl group with site-occupancy factors refined to 0.78 (5) and 0.22 (5).

Related literature

For anti­cancer activity of organometallic ruthenium complexes, see: Almodares et al. (2014 ▸); Stepanenko et al. (2011 ▸). For the use of a similar azo­pyridine ligand to stabilize ruthenium complexes, see: Velders et al. (2000 ▸). For related η-p-cymene ruthenium complexes, see: Singh et al. (2002 ▸), Kumar et al. (2008 ▸). For the crystal structure of an η-p-cymene ruthenium complex with an azo­pyridine ligand, see: Dougan et al. (2006 ▸).

Experimental

Crystal data

[RuCl(C10H14)(C11H10N4)]Cl

M = 504.41

Orthorhombic,

a = 8.9642 (8) Å

b = 17.6283 (16) Å

c = 26.976 (3) Å

V = 4262.8 (7) Å3

Z = 8

Mo Kα radiation

μ = 1.00 mm−1

T = 293 K

0.44 × 0.10 × 0.07 mm

Data collection

Bruker SMART APEX CCD Diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2003 ▸) T min = 0.693, T max = 1.000

40186 measured reflections

5127 independent reflections

4242 reflections with I > 2σ(I)

R int = 0.069

Refinement

R[F 2 > 2σ(F 2)] = 0.074

wR(F 2) = 0.136

S = 1.12

5127 reflections

265 parameters

15 restraints

H-atom parameters constrained

Δρmax = 0.71 e Å−3

Δρmin = −1.61 e Å−3

Data collection: SMART (Bruker, 1998 ▸); cell refinement: SAINT (Bruker, 2003 ▸); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▸); program(s) used to refine structure: SHELXL2012 (Sheldrick, 2015 ▸) and SHELXLE (Hübschle et al., 2011 ▸); molecular graphics: Mercury (Macrae et al., 2008 ▸); software used to prepare material for publication: SHELXL97 (Sheldrick, 2008 ▸) and publCIF (Westrip, 2010 ▸).

Crystal structure: contains datablock(s) I. DOI: 10.1107/S2056989015017466/zq2235sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S2056989015017466/zq2235Isup2.hkl

Click here for additional data file.

. DOI: 10.1107/S2056989015017466/zq2235fig1.tif

The mol­ecular structure of the title compound showing the atom-labelling scheme. Displacement ellipsoids are drawn at the 30% probability level.

Click here for additional data file.

a . DOI: 10.1107/S2056989015017466/zq2235fig2.tif

Crystal packing of the title compound showing the N—H⋯Cl hydrogen bonds along the a axis.

CCDC reference: 1425731

Additional supporting information: crystallographic information; 3D view; checkCIF report

[RuCl(C10H14)(C11H10N4)]Cl	Dx = 1.572 Mg m−3
Mr = 504.41	Mo Kα radiation, λ = 0.71073 Å
Orthorhombic, Pbca	Cell parameters from 7302 reflections
a = 8.9642 (8) Å	θ = 2.3–27.9°
b = 17.6283 (16) Å	µ = 1.00 mm−1
c = 26.976 (3) Å	T = 293 K
V = 4262.8 (7) Å3	Block, colorless
Z = 8	0.44 × 0.10 × 0.07 mm
F(000) = 2048

Bruker SMART APEX CCD Diffractometer	4242 reflections with I > 2σ(I)
Radiation source: sealed tube	Rint = 0.069
φ and ω scans	θmax = 28.0°, θmin = 1.5°
Absorption correction: multi-scan (SADABS; Bruker, 2003)	h = −11→11
Tmin = 0.693, Tmax = 1.000	k = −23→23
40186 measured reflections	l = −35→35
5127 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)] = 0.074	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.136	H-atom parameters constrained
S = 1.12	w = 1/[σ2(Fo2) + (0.0276P)2 + 25.095P] where P = (Fo2 + 2Fc2)/3
5127 reflections	(Δ/σ)max = 0.002
265 parameters	Δρmax = 0.71 e Å−3
15 restraints	Δρmin = −1.61 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.

	x	y	z	Uiso*/Ueq	Occ. (<1)
Ru1	0.62601 (5)	0.03668 (2)	0.38760 (2)	0.03006 (13)
Cl1	0.73313 (19)	−0.03312 (8)	0.45488 (5)	0.0473 (4)
Cl2	0.98928 (17)	−0.30554 (8)	0.21404 (6)	0.0434 (4)
N1	0.5259 (5)	−0.0663 (2)	0.37034 (16)	0.0298 (9)
N2	0.5993 (5)	−0.1133 (2)	0.34347 (16)	0.0310 (10)
N3	0.7791 (5)	−0.0169 (2)	0.34159 (16)	0.0283 (9)
N4	0.7774 (5)	−0.2032 (3)	0.28221 (19)	0.0450 (13)
H4A	0.8322	−0.2296	0.2625	0.054*
H4B	0.6955	−0.2218	0.2935	0.054*
C1	0.3803 (6)	−0.0944 (3)	0.3838 (2)	0.0352 (12)
C2	0.3052 (7)	−0.0609 (3)	0.4228 (2)	0.0410 (14)
H2	0.3527	−0.0249	0.4423	0.049*
C3	0.1594 (7)	−0.0812 (4)	0.4325 (3)	0.0511 (17)
H3	0.1065	−0.0564	0.4574	0.061*
C4	0.0923 (8)	−0.1376 (4)	0.4057 (3)	0.0571 (19)
H4	−0.0057	−0.1514	0.4125	0.069*
C5	0.1712 (8)	−0.1743 (4)	0.3684 (3)	0.0542 (18)
H5	0.1273	−0.2140	0.3510	0.065*
C6	0.3139 (7)	−0.1520 (3)	0.3573 (2)	0.0413 (14)
H6	0.3658	−0.1757	0.3318	0.050*
C7	0.7341 (6)	−0.0871 (3)	0.32750 (18)	0.0270 (10)
C8	0.8194 (6)	−0.1338 (3)	0.2952 (2)	0.0311 (11)
C9	0.9527 (6)	−0.1018 (3)	0.2774 (2)	0.0389 (13)
H9	1.0131	−0.1291	0.2558	0.047*
C10	0.9932 (7)	−0.0306 (3)	0.2921 (2)	0.0477 (15)
H10	1.0801	−0.0090	0.2796	0.057*
C11	0.9061 (6)	0.0096 (3)	0.3252 (2)	0.0396 (14)
H11	0.9388	0.0568	0.3361	0.048*
C12	0.6938 (7)	0.1496 (3)	0.4186 (2)	0.0374 (13)
C13	0.5524 (8)	0.1272 (3)	0.4388 (3)	0.0495 (17)
H13	0.5459	0.1158	0.4743	0.059*
C14	0.4329 (8)	0.1095 (3)	0.4089 (3)	0.0565 (19)
H14	0.3456	0.0853	0.4240	0.068*
C15	0.4465 (8)	0.1082 (3)	0.3565 (3)	0.0549 (18)
C16	0.5835 (7)	0.1301 (3)	0.3363 (2)	0.0447 (15)
H16	0.6012	0.1223	0.3008	0.054*
C17	0.7038 (7)	0.1516 (3)	0.3669 (2)	0.0382 (13)
H17	0.8028	0.1568	0.3518	0.046*
C18	0.3198 (8)	0.0843 (5)	0.3244 (3)	0.081 (3)
H18A	0.3575	0.0676	0.2929	0.121*
H18B	0.2536	0.1264	0.3195	0.121*
H18C	0.2667	0.0436	0.3401	0.121*
C19	0.8212 (9)	0.1721 (4)	0.4513 (3)	0.0580 (19)	0.78 (5)
H19	0.7999	0.1522	0.4845	0.070*	0.78 (5)
C20	0.9735 (12)	0.1408 (13)	0.4358 (7)	0.066 (4)	0.78 (5)
H20A	0.9682	0.0865	0.4335	0.099*	0.78 (5)
H20B	1.0471	0.1547	0.4600	0.099*	0.78 (5)
H20C	1.0006	0.1614	0.4041	0.099*	0.78 (5)
C21	0.824 (3)	0.2586 (7)	0.4555 (12)	0.111 (8)	0.78 (5)
H21A	0.9016	0.2735	0.4781	0.167*	0.78 (5)
H21B	0.7298	0.2763	0.4675	0.167*	0.78 (5)
H21C	0.8437	0.2802	0.4234	0.167*	0.78 (5)
C19B	0.8212 (9)	0.1721 (4)	0.4513 (3)	0.0580 (19)	0.22 (5)
H19B	0.8245	0.1339	0.4777	0.070*	0.22 (5)
C20B	0.974 (4)	0.169 (4)	0.426 (2)	0.066 (4)	0.22 (5)
H20D	0.9845	0.1215	0.4094	0.099*	0.22 (5)
H20E	1.0504	0.1738	0.4510	0.099*	0.22 (5)
H20F	0.9819	0.2098	0.4030	0.099*	0.22 (5)
C21B	0.791 (9)	0.247 (3)	0.477 (3)	0.111 (8)	0.22 (5)
H21D	0.8799	0.2637	0.4939	0.167*	0.22 (5)
H21E	0.7125	0.2405	0.5011	0.167*	0.22 (5)
H21F	0.7618	0.2844	0.4533	0.167*	0.22 (5)

	U11	U22	U33	U12	U13	U23
Ru1	0.0334 (2)	0.02129 (19)	0.0355 (2)	0.00223 (18)	0.00250 (19)	−0.00160 (17)
Cl1	0.0641 (10)	0.0363 (7)	0.0414 (8)	0.0089 (7)	−0.0093 (7)	0.0017 (6)
Cl2	0.0424 (8)	0.0322 (7)	0.0558 (9)	−0.0014 (6)	0.0150 (7)	−0.0051 (6)
N1	0.033 (2)	0.024 (2)	0.032 (2)	−0.0030 (19)	0.0057 (19)	−0.0007 (17)
N2	0.030 (2)	0.023 (2)	0.040 (2)	0.0006 (18)	0.0072 (19)	−0.0019 (18)
N3	0.028 (2)	0.021 (2)	0.036 (2)	−0.0013 (17)	−0.0003 (19)	−0.0040 (17)
N4	0.039 (3)	0.031 (3)	0.065 (3)	−0.004 (2)	0.019 (3)	−0.011 (2)
C1	0.032 (3)	0.032 (3)	0.041 (3)	−0.002 (2)	0.009 (3)	0.006 (2)
C2	0.043 (3)	0.036 (3)	0.044 (3)	0.002 (3)	0.011 (3)	0.001 (3)
C3	0.049 (4)	0.050 (4)	0.054 (4)	0.006 (3)	0.023 (3)	0.009 (3)
C4	0.036 (4)	0.069 (5)	0.066 (5)	−0.005 (3)	0.006 (3)	0.020 (4)
C5	0.047 (4)	0.047 (4)	0.069 (5)	−0.016 (3)	0.002 (3)	0.001 (3)
C6	0.038 (3)	0.037 (3)	0.049 (4)	−0.008 (3)	0.009 (3)	−0.004 (3)
C7	0.025 (2)	0.024 (2)	0.032 (3)	−0.001 (2)	0.000 (2)	0.000 (2)
C8	0.034 (3)	0.025 (3)	0.035 (3)	0.004 (2)	0.004 (2)	0.002 (2)
C9	0.031 (3)	0.040 (3)	0.046 (3)	0.008 (2)	0.010 (3)	−0.004 (3)
C10	0.036 (3)	0.045 (3)	0.062 (4)	−0.011 (3)	0.014 (3)	−0.006 (3)
C11	0.032 (3)	0.034 (3)	0.053 (4)	−0.004 (2)	0.010 (3)	−0.011 (3)
C12	0.060 (4)	0.015 (2)	0.037 (3)	0.001 (2)	0.004 (3)	0.002 (2)
C13	0.076 (5)	0.021 (3)	0.052 (4)	0.006 (3)	0.020 (4)	−0.004 (3)
C14	0.050 (4)	0.026 (3)	0.093 (6)	0.011 (3)	0.019 (4)	−0.005 (3)
C15	0.048 (4)	0.030 (3)	0.087 (5)	0.011 (3)	−0.014 (4)	0.002 (3)
C16	0.055 (4)	0.031 (3)	0.049 (4)	0.010 (3)	−0.007 (3)	0.008 (3)
C17	0.045 (3)	0.024 (3)	0.045 (3)	0.003 (3)	0.002 (3)	0.006 (2)
C18	0.053 (5)	0.064 (5)	0.126 (8)	0.007 (4)	−0.038 (5)	0.020 (5)
C19	0.089 (6)	0.036 (3)	0.049 (4)	−0.013 (4)	−0.013 (4)	−0.012 (3)
C20	0.066 (6)	0.064 (10)	0.068 (8)	−0.018 (6)	−0.016 (5)	−0.002 (7)
C21	0.147 (15)	0.048 (6)	0.14 (2)	−0.010 (8)	−0.054 (14)	−0.032 (9)
C19B	0.089 (6)	0.036 (3)	0.049 (4)	−0.013 (4)	−0.013 (4)	−0.012 (3)
C20B	0.066 (6)	0.064 (10)	0.068 (8)	−0.018 (6)	−0.016 (5)	−0.002 (7)
C21B	0.147 (15)	0.048 (6)	0.14 (2)	−0.010 (8)	−0.054 (14)	−0.032 (9)

Ru1—N3	2.077 (4)	C10—H10	0.9300
Ru1—N1	2.078 (4)	C11—H11	0.9300
Ru1—C16	2.185 (6)	C12—C17	1.398 (8)
Ru1—C15	2.210 (6)	C12—C13	1.435 (9)
Ru1—C13	2.211 (6)	C12—C19	1.498 (9)
Ru1—C17	2.215 (5)	C13—C14	1.376 (10)
Ru1—C14	2.231 (6)	C13—H13	0.9800
Ru1—C12	2.243 (5)	C14—C15	1.419 (10)
Ru1—Cl1	2.3938 (15)	C14—H14	0.9800
N1—N2	1.283 (6)	C15—C16	1.398 (9)
N1—C1	1.442 (7)	C15—C18	1.489 (10)
N2—C7	1.363 (6)	C16—C17	1.411 (8)
N3—C11	1.307 (7)	C16—H16	0.9800
N3—C7	1.356 (6)	C17—H17	0.9800
N4—C8	1.327 (7)	C18—H18A	0.9600
N4—H4A	0.8600	C18—H18B	0.9600
N4—H4B	0.8600	C18—H18C	0.9600
C1—C6	1.376 (8)	C19—C21	1.529 (12)
C1—C2	1.381 (8)	C19—C20	1.531 (12)
C2—C3	1.381 (8)	C19—H19	0.9800
C2—H2	0.9300	C20—H20A	0.9600
C3—C4	1.368 (10)	C20—H20B	0.9600
C3—H3	0.9300	C20—H20C	0.9600
C4—C5	1.389 (10)	C21—H21A	0.9600
C4—H4	0.9300	C21—H21B	0.9600
C5—C6	1.371 (8)	C21—H21C	0.9600
C5—H5	0.9300	C20B—H20D	0.9600
C6—H6	0.9300	C20B—H20E	0.9600
C7—C8	1.422 (7)	C20B—H20F	0.9600
C8—C9	1.406 (8)	C21B—H21D	0.9600
C9—C10	1.365 (8)	C21B—H21E	0.9600
C9—H9	0.9300	C21B—H21F	0.9600
C10—C11	1.382 (8)
N3—Ru1—N1	75.80 (16)	C9—C10—C11	120.6 (5)
N3—Ru1—C16	94.5 (2)	C9—C10—H10	119.7
N1—Ru1—C16	116.2 (2)	C11—C10—H10	119.7
N3—Ru1—C15	120.9 (2)	N3—C11—C10	121.8 (5)
N1—Ru1—C15	95.7 (2)	N3—C11—H11	119.1
C16—Ru1—C15	37.1 (2)	C10—C11—H11	119.1
N3—Ru1—C13	153.9 (2)	C17—C12—C13	116.3 (6)
N1—Ru1—C13	129.9 (2)	C17—C12—C19	122.2 (6)
C16—Ru1—C13	78.4 (2)	C13—C12—C19	121.5 (6)
C15—Ru1—C13	66.9 (3)	C17—C12—Ru1	70.6 (3)
N3—Ru1—C17	93.25 (19)	C13—C12—Ru1	70.0 (3)
N1—Ru1—C17	151.50 (19)	C19—C12—Ru1	131.4 (4)
C16—Ru1—C17	37.4 (2)	C14—C13—C12	121.9 (6)
C15—Ru1—C17	67.1 (2)	C14—C13—Ru1	72.7 (4)
C13—Ru1—C17	65.9 (2)	C12—C13—Ru1	72.4 (3)
N3—Ru1—C14	158.2 (2)	C14—C13—H13	118.6
N1—Ru1—C14	103.0 (2)	C12—C13—H13	118.6
C16—Ru1—C14	66.1 (3)	Ru1—C13—H13	118.6
C15—Ru1—C14	37.3 (3)	C13—C14—C15	121.3 (7)
C13—Ru1—C14	36.1 (3)	C13—C14—Ru1	71.2 (4)
C17—Ru1—C14	77.5 (2)	C15—C14—Ru1	70.6 (4)
N3—Ru1—C12	116.54 (19)	C13—C14—H14	118.5
N1—Ru1—C12	167.39 (19)	C15—C14—H14	118.5
C16—Ru1—C12	67.3 (2)	Ru1—C14—H14	118.5
C15—Ru1—C12	80.3 (2)	C16—C15—C14	117.4 (7)
C13—Ru1—C12	37.6 (2)	C16—C15—C18	121.3 (7)
C17—Ru1—C12	36.5 (2)	C14—C15—C18	121.2 (7)
C14—Ru1—C12	66.6 (2)	C16—C15—Ru1	70.5 (3)
N3—Ru1—Cl1	87.39 (12)	C14—C15—Ru1	72.2 (4)
N1—Ru1—Cl1	83.92 (13)	C18—C15—Ru1	127.9 (5)
C16—Ru1—Cl1	159.70 (18)	C15—C16—C17	121.1 (6)
C15—Ru1—Cl1	150.8 (2)	C15—C16—Ru1	72.4 (4)
C13—Ru1—Cl1	91.00 (19)	C17—C16—Ru1	72.5 (3)
C17—Ru1—Cl1	122.36 (16)	C15—C16—H16	119.1
C14—Ru1—Cl1	114.3 (2)	C17—C16—H16	119.1
C12—Ru1—Cl1	93.73 (15)	Ru1—C16—H16	119.1
N2—N1—C1	112.6 (4)	C12—C17—C16	121.9 (6)
N2—N1—Ru1	118.0 (3)	C12—C17—Ru1	72.8 (3)
C1—N1—Ru1	129.4 (3)	C16—C17—Ru1	70.1 (3)
N1—N2—C7	114.5 (4)	C12—C17—H17	118.3
C11—N3—C7	119.4 (4)	C16—C17—H17	118.3
C11—N3—Ru1	128.0 (4)	Ru1—C17—H17	118.3
C7—N3—Ru1	112.7 (3)	C15—C18—H18A	109.5
C8—N4—H4A	120.0	C15—C18—H18B	109.5
C8—N4—H4B	120.0	H18A—C18—H18B	109.5
H4A—N4—H4B	120.0	C15—C18—H18C	109.5
C6—C1—C2	120.0 (5)	H18A—C18—H18C	109.5
C6—C1—N1	120.9 (5)	H18B—C18—H18C	109.5
C2—C1—N1	119.0 (5)	C12—C19—C21	108.7 (9)
C3—C2—C1	119.8 (6)	C12—C19—C20	115.0 (7)
C3—C2—H2	120.1	C21—C19—C20	111.3 (10)
C1—C2—H2	120.1	C12—C19—H19	107.2
C4—C3—C2	120.2 (6)	C21—C19—H19	107.2
C4—C3—H3	119.9	C20—C19—H19	107.2
C2—C3—H3	119.9	C19—C20—H20A	109.5
C3—C4—C5	119.8 (6)	C19—C20—H20B	109.5
C3—C4—H4	120.1	H20A—C20—H20B	109.5
C5—C4—H4	120.1	C19—C20—H20C	109.5
C6—C5—C4	120.0 (7)	H20A—C20—H20C	109.5
C6—C5—H5	120.0	H20B—C20—H20C	109.5
C4—C5—H5	120.0	C19—C21—H21A	109.5
C5—C6—C1	120.0 (6)	C19—C21—H21B	109.5
C5—C6—H6	120.0	H21A—C21—H21B	109.5
C1—C6—H6	120.0	C19—C21—H21C	109.5
N3—C7—N2	119.0 (4)	H21A—C21—H21C	109.5
N3—C7—C8	122.7 (5)	H21B—C21—H21C	109.5
N2—C7—C8	118.2 (4)	H20D—C20B—H20E	109.5
N4—C8—C9	121.4 (5)	H20D—C20B—H20F	109.5
N4—C8—C7	123.0 (5)	H20E—C20B—H20F	109.5
C9—C8—C7	115.7 (5)	H21D—C21B—H21E	109.5
C10—C9—C8	119.8 (5)	H21D—C21B—H21F	109.5
C10—C9—H9	120.1	H21E—C21B—H21F	109.5
C8—C9—H9	120.1
C1—N1—N2—C7	176.3 (4)	C19—C12—C13—C14	177.3 (6)
Ru1—N1—N2—C7	−3.0 (6)	Ru1—C12—C13—C14	−55.7 (5)
N2—N1—C1—C6	−19.8 (7)	C17—C12—C13—Ru1	55.0 (4)
Ru1—N1—C1—C6	159.5 (4)	C19—C12—C13—Ru1	−127.0 (5)
N2—N1—C1—C2	162.6 (5)	C12—C13—C14—C15	3.7 (9)
Ru1—N1—C1—C2	−18.2 (7)	Ru1—C13—C14—C15	−51.8 (5)
C6—C1—C2—C3	−5.1 (9)	C12—C13—C14—Ru1	55.5 (5)
N1—C1—C2—C3	172.7 (5)	C13—C14—C15—C16	−3.7 (9)
C1—C2—C3—C4	4.1 (10)	Ru1—C14—C15—C16	−55.8 (5)
C2—C3—C4—C5	−0.3 (10)	C13—C14—C15—C18	176.1 (6)
C3—C4—C5—C6	−2.5 (11)	Ru1—C14—C15—C18	124.0 (6)
C4—C5—C6—C1	1.5 (10)	C13—C14—C15—Ru1	52.1 (5)
C2—C1—C6—C5	2.3 (9)	C14—C15—C16—C17	0.7 (9)
N1—C1—C6—C5	−175.4 (6)	C18—C15—C16—C17	−179.1 (6)
C11—N3—C7—N2	−177.9 (5)	Ru1—C15—C16—C17	−55.9 (5)
Ru1—N3—C7—N2	1.0 (6)	C14—C15—C16—Ru1	56.6 (5)
C11—N3—C7—C8	−0.1 (8)	C18—C15—C16—Ru1	−123.2 (6)
Ru1—N3—C7—C8	178.8 (4)	C13—C12—C17—C16	−2.3 (8)
N1—N2—C7—N3	1.3 (7)	C19—C12—C17—C16	179.7 (5)
N1—N2—C7—C8	−176.6 (4)	Ru1—C12—C17—C16	52.4 (5)
N3—C7—C8—N4	178.4 (5)	C13—C12—C17—Ru1	−54.7 (4)
N2—C7—C8—N4	−3.8 (8)	C19—C12—C17—Ru1	127.4 (5)
N3—C7—C8—C9	−1.8 (7)	C15—C16—C17—C12	2.3 (9)
N2—C7—C8—C9	176.0 (5)	Ru1—C16—C17—C12	−53.6 (5)
N4—C8—C9—C10	−179.2 (6)	C15—C16—C17—Ru1	55.9 (5)
C7—C8—C9—C10	0.9 (8)	C17—C12—C19—C21	81.0 (17)
C8—C9—C10—C11	1.6 (10)	C13—C12—C19—C21	−96.8 (16)
C7—N3—C11—C10	2.9 (9)	Ru1—C12—C19—C21	172.9 (15)
Ru1—N3—C11—C10	−175.8 (5)	C17—C12—C19—C20	−44.5 (14)
C9—C10—C11—N3	−3.7 (10)	C13—C12—C19—C20	137.7 (12)
C17—C12—C13—C14	−0.7 (8)	Ru1—C12—C19—C20	47.4 (13)

D—H···A	D—H	H···A	D···A	D—H···A
N4—H4A···Cl2	0.86	2.34	3.200 (5)	176
N4—H4B···Cl2i	0.86	2.37	3.152 (5)	151

Table 1

Hydrogen-bond geometry (, )

DHA	DH	HA	D A	DHA
N4H4ACl2	0.86	2.34	3.200(5)	176
N4H4BCl2i	0.86	2.37	3.152(5)	151

Symmetry code: (i) .