Chlorido­(η6-p-cymene)[2-(5-phenyl-4H-1,2,4-triazol-3-yl-κN2)pyridine-κN]ruthenium(II) chloride

Sikalov, A.

doi:10.1107/S2414314618006259

metal-organic compounds

IUCrDATA

ISSN: 2414-3146

Volume 3| Part 5| May 2018| x180625

https://doi.org/10.1107/S2414314618006259

Open

access

ADDENDA AND ERRATA
A correction has been published for this article. To view the correction, click here.

Chlorido(η⁶-p-cymene)[2-(5-phenyl-4H-1,2,4-triazol-3-yl-κN²)pyridine-κN]ruthenium(II) chloride

Alexander Sikalov ^a ^*

^aVolodymyrska 64 Street, Kiev, Ukraine
^*Correspondence e-mail: a.a.sikalov@gmail.com

Edited by J. Simpson, University of Otago, New Zealand (Received 29 March 2018; accepted 24 April 2018; online 4 May 2018)

In the title compound, [RuCl(C₁₀H₁₄)(C₁₃H₁₀N₄)]Cl, the pyridyltriazole fragment of the bidentate ligand is essentially planar [dihedral angle = 0.8 (1)°], while the phenyl substituent is inclined at 19.4 (1)° to the 1,2,4-triazole ring. In the crystal, the complex cations are packed in sheets with no particularly strong interactions between them. The Cl⁻ anions are bound to the cations by unusually strong N—H⋯Cl hydrogen bonds.

Keywords: crystal structure; ruthenium; p-cymene; coordination chemistry; hydrogen bonding; pyridyltriazoles.

CCDC reference: 1839210

Structure description

Recently, ruthenium(II) π-arene complexes have been of increasing interest – mostly due to their anticancer properties (Süss-Fink, 2010 ) and their catalytic activity in transfer hydrogenation reactions (Hohloch et al., 2013 ). Therefore, it is of great importance to know the structural details of these compounds. We have synthesized an example of a ruthenium(II) p-cymene complex with a pyridyl-1,2,4-triazole ligand in the 4H-tautomeric form. The molecular structure of the title compound is shown in Fig. 1. As is traditional for this kind of compounds, the cation exhibits a distorted octahedral piano-stool geometry with p-cymene as a π-bound hexahapto ligand, a chloride anion as a monodentate ligand and the 3-(2-pyridyl)-5-phenyl-1,2,4-triazole as a bidentate chelating N,N-donor ligand. It is interesting that while the pyridyltriazole moiety is virtually planar with a dihedral angle of a mere 0.8 (1)° between the pyridine and triazole rings, the phenyl ring does not lie in this plane and is inclined at 19.4 (1)° to the triazole ring plane, even though there is no apparent steric hindrance to cause this. We surmise that the fact that the 2-(5-phenyl-4H-1,2,4-triazol-3-yl)pyridine ligand is coordinated via N4 arises from unfavourable steric interactions (between the phenyl group and the p-cymene ligand), which would take place in a hypothetical analogue of the title compound where the ligand is coordinated via N7.

Figure 1
The title compound with displacement ellipsoids drawn at the 50% probability level. H atoms are shown as spheres of arbitrary radius.

As shown in Fig. 2, the title compound features an intriguing hydrogen bond formed between the N—H group of the 1,2,4-triazole ring and the chloride counter-ion (Table 1). The relatively short H⋯Cl distance and an NH⋯Cl angle close to 180° suggest an atypical strength of the bond as compared to other N—H⋯Cl hydrogen bonds, excluding charge-assisted hydrogen bonds (Steed & Atwood, 2009 ). Unexpectedly, the title compound does not exhibit any significant π-stacking interactions [the shortest centroid–centroid distance is 4.122 Å (offset) and the shortest C—H⋯centroid distance is 3.453 Å].

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N7—H71⋯Cl3	0.85	2.15	2.984	169

Figure 2
A crystal packing diagram (view along the b axis) of the title compound. N—H⋯Cl hydrogen bonds are depicted as blue dashed lines.

It appears that crystal structures of ruthenium(II) p-cymene complexes bearing 3-(2-pyridyl)-1,2,4-triazoles have not been published until now. The two most closely related crystal structures are those of η⁵-cyclopentadienyl analogues, which also differ from the title compound by variations in the 3-(2-pyridyl)-1,2,4-triazole ligands and by replacement of the chlorido ligand by PPh₃ in the inner coordination sphere. The Ru1—N4 and Ru1—N5 bond lengths [2.072 (3) and 2.132 (2) Å, respectively] in the title compound are comparable to those in the related compounds mentioned above [respective bond distances are 2.069 (3) and 2.125 (3) Å (Gupta et al., 2010 ) and 2.089 (4) and 2.119 (3) Å (Gupta et al., 2012 )].

Synthesis and crystallization

The ruthenium(II) p-cymene dichloride dimer (244.8 mg, 0.4 mmol) was dissolved in about 3 ml of methanol. After complete dissolution of the starting compound, 2-(5-phenyl-4H-1,2,4-triazol-3-yl)pyridine (355.2 mg, 0.8 mmol) was added to the clear red solution. Within 30 minutes, the reaction mixture adopted a reddish–orange hue and red prismatic crystals suitable for single-crystal XRD analysis began to form on the bottom and sides of the reaction vessel. Several crystals were harvested, and then the solvent was distilled off with the use of a rotary evaporator. Yield: 93%. Schematic representation of the synthesis is given in Fig. 3.

Figure 3
Synthesis of the title compound.

¹H NMR (400 MHz, DMSO-δ₆): δ(p.p.m.) 9.43 (d, J = 4.2 Hz, 1H, py^αH), 8.30–8.08 (m, 3H, py^βH, py^β′H and py^γH), 7.83–7.26 (m, 5H, phenyl), 6.14 (d, J = 5.0 Hz, 1H, p-cymene CH), 6.02 (d, J = 4.9 Hz, 1H, p-cymene CH), 5.93 (d, J = 4.9 Hz, 1H, p-cymene CH), 5.80 (d, J = 5.0 Hz, 1H, p-cymene CH), 2.74–2.63 (m, 1H, CH from ⁱPr), 2.17 (s, 3H, Me from p-cymene), 1.06 (d, J = 6.8 Hz, 3H, Me from ⁱPr), 0.98 (d, J = 6.7 Hz, 3H, Me from ⁱPr).

Refinement

Crystal data, data collection and structure refinement details are summarized in Table 2.

Table 2
Experimental details

Crystal data
Chemical formula	[RuCl(C₁₀H₁₄)(C₁₃H₁₀N₄)]Cl
M_r	528.44
Crystal system, space group	Triclinic, P1
Temperature (K)	200
a, b, c (Å)	6.4704 (2), 8.7593 (3), 10.1975 (4)
α, β, γ (°)	101.425 (3), 97.379 (3), 95.337 (3)
V (Å³)	557.62 (3)
Z	1
Radiation type	Mo Kα
μ (mm⁻¹)	0.96
Crystal size (mm)	0.35 × 0.20 × 0.20

Data collection
Diffractometer	Agilent Xcalibur, Eos with CCD area detector
Absorption correction	Multi-scan (DENZO/SCALEPACK; Otwinowski & Minor, 1997 )
T_min, T_max	0.81, 0.83
No. of measured, independent and observed [I > 2.0σ(I)] reflections	13071, 7295, 7220
R_int	0.028
(sin θ/λ)_max (Å⁻¹)	0.760

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.032, 0.062, 0.98
No. of reflections	7295
No. of parameters	276
No. of restraints	7
H-atom treatment	H atoms treated by a mixture of independent and constrained refinement
Δρ_max, Δρ_min (e Å⁻³)	0.56, −0.40
Absolute structure	Flack (1983 ), 3505 Friedel-pairs
Absolute structure parameter	−0.03 (2)
Computer programs: CrysAlis PRO (Agilent, 2014 ), SHELXS97 (Sheldrick, 2008 ), CRYSTALS (Betteridge et al., 2003 ), Mercury (Macrae et al., 2006 ), publCIF (Westrip, 2010 ).

Structural data

CCDC reference: 1839210

Crystal structure: contains datablocks global, I. DOI: https://doi.org/10.1107/S2414314618006259/sj4174sup1.cif

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S2414314618006259/sj4174Isup2.hkl

checkCIF report

Computing details top

Data collection: CrysAlis PRO (Agilent, 2014); cell refinement: CrysAlis PRO (Agilent, 2014); data reduction: CrysAlis PRO (Agilent, 2014); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: CRYSTALS (Betteridge et al., 2003); molecular graphics: Mercury (Macrae et al., 2006); software used to prepare material for publication: publCIF (Westrip, 2010).

Chlorido(η⁶-p-cymene)[2-(5-phenyl-4H-1,2,4-triazol-3-yl-κN²)pyridine-κN]ruthenium(II) chloride top

Crystal data top

[RuCl(C₁₀H₁₄)(C₁₃H₁₀N₄)]Cl	Z = 1
M_r = 528.44	F(000) = 267.999
Triclinic, P1	D_x = 1.574 Mg m⁻³
Hall symbol: P 1	Mo Kα radiation, λ = 0.71073 Å
a = 6.4704 (2) Å	Cell parameters from 8029 reflections
b = 8.7593 (3) Å	θ = 2–32°
c = 10.1975 (4) Å	µ = 0.96 mm⁻¹
α = 101.425 (3)°	T = 200 K
β = 97.379 (3)°	Prism, clear intense red
γ = 95.337 (3)°	0.35 × 0.20 × 0.20 mm
V = 557.62 (3) Å³

Data collection top

Agilent Xcalibur, Eos with CCD area detector diffractometer	7220 reflections with I > 2.0σ(I)
Graphite monochromator	R_int = 0.028
ω scans	θ_max = 32.7°, θ_min = 2.1°
Absorption correction: multi-scan (DENZO/SCALEPACK; Otwinowski & Minor, 1997)	h = −9→9
T_min = 0.81, T_max = 0.83	k = −13→13
13071 measured reflections	l = −15→15
7295 independent reflections

Refinement top

Refinement on F²	Hydrogen site location: difference Fourier map
Least-squares matrix: full	H atoms treated by a mixture of independent and constrained refinement
R[F² > 2σ(F²)] = 0.032	Method = Modified Sheldrick w = 1/[σ²(F²) + ( 0.02P)² + 0.15P] , where P = (max(F_o²,0) + 2F_c²)/3
wR(F²) = 0.062	(Δ/σ)_max = 0.001
S = 0.98	Δρ_max = 0.56 e Å⁻³
7295 reflections	Δρ_min = −0.40 e Å⁻³
276 parameters	Absolute structure: Flack (1983), 3505 Friedel-pairs
7 restraints	Absolute structure parameter: −0.03 (2)
Primary atom site location: other

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å²) top

	x	y	z	U_iso*/U_eq
Ru1	0.86321 (8)	0.38802 (6)	0.54014 (6)	0.0176
Cl2	0.67364 (12)	0.60046 (10)	0.49812 (9)	0.0272
Cl3	0.38532 (13)	0.18193 (12)	−0.10651 (9)	0.0382
N4	0.6317 (4)	0.2491 (3)	0.3951 (2)	0.0217
N5	0.9711 (4)	0.4024 (3)	0.3535 (2)	0.0205
N6	0.4495 (3)	0.1562 (3)	0.3969 (2)	0.0224
N7	0.4792 (3)	0.1708 (3)	0.1855 (2)	0.0220
C8	1.0648 (5)	0.5307 (4)	0.7248 (3)	0.0242
C9	0.6471 (4)	0.2555 (3)	0.2682 (2)	0.0197
C10	0.7853 (5)	0.3174 (4)	0.7245 (3)	0.0269
C11	1.1560 (4)	0.4760 (3)	0.3399 (3)	0.0252
C12	0.3595 (4)	0.1103 (3)	0.2695 (3)	0.0212
C13	0.8319 (4)	0.3402 (3)	0.2389 (3)	0.0217
C14	1.1769 (4)	0.4165 (3)	0.6582 (3)	0.0266
C15	0.8723 (4)	0.3530 (3)	0.1111 (3)	0.0294
C16	0.8650 (4)	0.4755 (3)	0.7562 (3)	0.0269
C17	0.1609 (4)	0.0092 (3)	0.2237 (3)	0.0227
C18	−0.1477 (6)	−0.0882 (5)	0.0591 (4)	0.0390
C19	1.0659 (4)	0.4275 (4)	0.0989 (3)	0.0318
C20	1.2075 (4)	0.4896 (4)	0.2144 (3)	0.0299
C21	0.9010 (4)	0.2016 (3)	0.6564 (3)	0.0276
C22	1.1445 (4)	0.7045 (3)	0.7648 (3)	0.0300
C23	0.0847 (5)	−0.0834 (4)	0.3077 (3)	0.0350
C24	1.0990 (4)	0.2552 (4)	0.6249 (3)	0.0279
C25	−0.2238 (5)	−0.1779 (4)	0.1438 (3)	0.0421
C26	0.0434 (4)	0.0051 (4)	0.0982 (3)	0.0310
C27	1.2355 (5)	0.7703 (4)	0.6552 (3)	0.0395
C28	−0.1071 (5)	−0.1770 (4)	0.2670 (3)	0.0433
C29	0.8085 (6)	0.0338 (4)	0.6203 (4)	0.0445
C30	1.3064 (6)	0.7305 (4)	0.8939 (4)	0.0505
H71	0.451 (3)	0.160 (3)	0.1007 (18)	0.0278 (19)*
H111	1.2519	0.5190	0.4165	0.0292*
H141	1.3038	0.4499	0.6226	0.0345*
H151	0.7718	0.3117	0.0351	0.0363*
H161	0.7756	0.5545	0.7899	0.0341*
H181	−0.2263	−0.0894	−0.0232	0.0473*
H191	1.1020	0.4339	0.0136	0.0391*
H201	1.3382	0.5360	0.2072	0.0359*
H221	1.0243	0.7611	0.7874	0.0381*
H231	0.1642	−0.0822	0.3918	0.0421*
H241	1.1754	0.1828	0.5704	0.0352*
H251	−0.3543	−0.2396	0.1181	0.0508*
H261	0.0930	0.0653	0.0394	0.0384*
H271	1.3590	0.7220	0.6351	0.0610*
H272	1.2764	0.8813	0.6860	0.0609*
H273	1.1347	0.7520	0.5733	0.0611*
H281	−0.1561	−0.2397	0.3228	0.0532*
H291	0.8511	−0.0189	0.5382	0.0682*
H293	0.8554	−0.0149	0.6927	0.0682*
H292	0.6578	0.0253	0.6089	0.0680*
H301	1.2398	0.7033	0.9668	0.0790*
H303	1.4155	0.6662	0.8771	0.0789*
H302	1.3657	0.8396	0.9189	0.0788*
H101	0.6409	0.2853	0.7369	0.0348*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Ru1	0.01437 (7)	0.02394 (8)	0.01423 (7)	0.00019 (5)	0.00201 (5)	0.00478 (6)
Cl2	0.0199 (3)	0.0299 (3)	0.0327 (4)	0.0052 (3)	0.0026 (3)	0.0090 (3)
Cl3	0.0336 (4)	0.0593 (5)	0.0200 (3)	−0.0087 (3)	0.0005 (3)	0.0134 (3)
N4	0.0213 (11)	0.0260 (11)	0.0172 (12)	−0.0043 (9)	0.0043 (9)	0.0054 (9)
N5	0.0156 (10)	0.0278 (12)	0.0182 (10)	0.0016 (9)	0.0031 (8)	0.0055 (9)
N6	0.0204 (10)	0.0244 (10)	0.0204 (10)	−0.0055 (8)	0.0013 (8)	0.0052 (8)
N7	0.0222 (10)	0.0261 (11)	0.0165 (10)	−0.0041 (8)	0.0020 (8)	0.0052 (8)
C8	0.0198 (13)	0.0308 (15)	0.0185 (15)	−0.0021 (11)	−0.0049 (10)	0.0041 (12)
C9	0.0194 (11)	0.0237 (12)	0.0156 (11)	−0.0009 (9)	0.0022 (8)	0.0053 (9)
C10	0.0234 (14)	0.0414 (18)	0.0177 (12)	−0.0001 (12)	0.0040 (10)	0.0121 (13)
C11	0.0186 (11)	0.0336 (14)	0.0226 (12)	−0.0014 (10)	0.0041 (9)	0.0058 (11)
C12	0.0193 (11)	0.0235 (12)	0.0211 (12)	0.0004 (9)	0.0043 (9)	0.0056 (10)
C13	0.0185 (11)	0.0261 (12)	0.0198 (12)	−0.0011 (9)	0.0022 (9)	0.0055 (10)
C14	0.0184 (11)	0.0393 (15)	0.0224 (12)	0.0025 (10)	−0.0030 (9)	0.0119 (11)
C15	0.0288 (14)	0.0392 (15)	0.0193 (12)	−0.0043 (12)	0.0043 (10)	0.0073 (11)
C16	0.0259 (13)	0.0371 (15)	0.0159 (11)	0.0025 (11)	0.0019 (9)	0.0030 (11)
C17	0.0212 (11)	0.0231 (12)	0.0224 (12)	−0.0026 (9)	0.0029 (9)	0.0038 (10)
C18	0.0271 (14)	0.052 (3)	0.032 (2)	−0.0112 (16)	−0.0040 (14)	0.0070 (18)
C19	0.0312 (14)	0.0440 (17)	0.0217 (13)	−0.0024 (12)	0.0088 (11)	0.0106 (12)
C20	0.0210 (12)	0.0405 (16)	0.0293 (14)	−0.0038 (11)	0.0085 (10)	0.0103 (12)
C21	0.0326 (14)	0.0282 (13)	0.0220 (12)	0.0020 (11)	−0.0011 (10)	0.0094 (10)
C22	0.0247 (13)	0.0341 (15)	0.0262 (13)	0.0011 (11)	−0.0008 (10)	−0.0013 (11)
C23	0.0360 (15)	0.0386 (16)	0.0280 (14)	−0.0129 (13)	−0.0004 (12)	0.0127 (12)
C24	0.0260 (14)	0.0356 (16)	0.0238 (14)	0.0114 (12)	0.0006 (11)	0.0088 (12)
C25	0.0306 (15)	0.0471 (19)	0.0424 (18)	−0.0161 (13)	0.0014 (13)	0.0071 (15)
C26	0.0255 (13)	0.0375 (16)	0.0279 (14)	−0.0049 (11)	0.0017 (11)	0.0073 (12)
C27	0.0418 (17)	0.0321 (15)	0.0435 (18)	−0.0019 (13)	0.0135 (14)	0.0037 (14)
C28	0.0392 (17)	0.0482 (19)	0.0393 (18)	−0.0180 (15)	0.0049 (14)	0.0131 (15)
C29	0.051 (2)	0.0342 (16)	0.050 (2)	0.0026 (15)	0.0041 (16)	0.0180 (15)
C30	0.051 (2)	0.048 (2)	0.0396 (19)	−0.0053 (17)	−0.0179 (16)	−0.0004 (16)

Geometric parameters (Å, º) top

Ru1—Cl2	2.399 (3)	C15—H151	0.933
Ru1—N4	2.072 (3)	C16—H161	0.981
Ru1—N5	2.132 (2)	C17—C23	1.394 (4)
Ru1—C8	2.223 (3)	C17—C26	1.394 (4)
Ru1—C10	2.195 (3)	C18—C25	1.382 (5)
Ru1—C14	2.189 (3)	C18—C26	1.383 (5)
Ru1—C16	2.183 (3)	C18—H181	0.922
Ru1—C21	2.213 (3)	C19—C20	1.378 (4)
Ru1—C24	2.195 (3)	C19—H191	0.940
N4—N6	1.373 (3)	C20—H201	0.922
N4—C9	1.322 (3)	C21—C24	1.421 (4)
N5—C11	1.342 (3)	C21—C29	1.490 (4)
N5—C13	1.363 (4)	C22—C27	1.513 (4)
N6—C12	1.320 (3)	C22—C30	1.538 (4)
N7—C9	1.345 (3)	C22—H221	0.988
N7—C12	1.374 (3)	C23—C28	1.388 (4)
N7—H71	0.846 (17)	C23—H231	0.939
C8—C14	1.407 (4)	C24—H241	0.972
C8—C16	1.435 (4)	C25—C28	1.379 (5)
C8—C22	1.518 (4)	C25—H251	0.936
C9—C13	1.444 (3)	C26—H261	0.940
C10—C16	1.391 (4)	C27—H271	0.964
C10—C21	1.438 (4)	C27—H272	0.961
C10—H101	0.982	C27—H273	0.967
C11—C20	1.388 (4)	C28—H281	0.930
C11—H111	0.924	C29—H291	0.959
C12—C17	1.458 (3)	C29—H293	0.955
C13—C15	1.386 (3)	C29—H292	0.961
C14—C24	1.414 (4)	C30—H301	0.963
C14—H141	0.983	C30—H303	0.955
C15—C19	1.390 (4)	C30—H302	0.967

Cl2—Ru1—N4	84.77 (8)	Ru1—C14—H141	122.1
Cl2—Ru1—N5	83.97 (7)	C8—C14—H141	119.4
N4—Ru1—N5	76.14 (9)	C24—C14—H141	118.0
Cl2—Ru1—C8	94.13 (9)	C13—C15—C19	118.5 (3)
N4—Ru1—C8	168.20 (9)	C13—C15—H151	120.5
N5—Ru1—C8	115.48 (10)	C19—C15—H151	121.0
Cl2—Ru1—C10	109.97 (9)	Ru1—C16—C8	72.50 (16)
N4—Ru1—C10	101.13 (11)	Ru1—C16—C10	71.95 (16)
N5—Ru1—C10	165.66 (9)	C8—C16—C10	122.3 (3)
C8—Ru1—C10	68.16 (12)	Ru1—C16—H161	121.8
Cl2—Ru1—C14	124.65 (8)	C8—C16—H161	117.5
N4—Ru1—C14	148.83 (11)	C10—C16—H161	119.7
N5—Ru1—C14	95.31 (9)	C12—C17—C23	119.5 (2)
C8—Ru1—C14	37.19 (11)	C12—C17—C26	121.3 (2)
C10—Ru1—C14	79.71 (11)	C23—C17—C26	119.2 (2)
Cl2—Ru1—C16	88.32 (8)	C25—C18—C26	120.5 (4)
N4—Ru1—C16	130.20 (10)	C25—C18—H181	119.6
N5—Ru1—C16	151.76 (10)	C26—C18—H181	119.9
C8—Ru1—C16	38.00 (11)	C15—C19—C20	118.8 (2)
C10—Ru1—C16	37.05 (11)	C15—C19—H191	121.1
Cl2—Ru1—C21	146.94 (8)	C20—C19—H191	120.1
N4—Ru1—C21	93.12 (10)	C11—C20—C19	119.9 (2)
N5—Ru1—C21	127.60 (10)	C11—C20—H201	120.5
C8—Ru1—C21	81.38 (11)	C19—C20—H201	119.6
C10—Ru1—C21	38.07 (11)	Ru1—C21—C10	70.29 (16)
Cl2—Ru1—C24	161.72 (8)	Ru1—C21—C24	70.50 (15)
N4—Ru1—C24	113.51 (12)	C10—C21—C24	117.4 (3)
N5—Ru1—C24	100.26 (10)	Ru1—C21—C29	129.3 (2)
C8—Ru1—C24	67.92 (12)	C10—C21—C29	119.4 (3)
C10—Ru1—C24	67.60 (11)	C24—C21—C29	123.3 (3)
C14—Ru1—C16	67.15 (10)	C8—C22—C27	114.4 (2)
C14—Ru1—C21	68.15 (10)	C8—C22—C30	107.7 (3)
C16—Ru1—C21	68.00 (11)	C27—C22—C30	111.2 (3)
C14—Ru1—C24	37.62 (11)	C8—C22—H221	107.5
C16—Ru1—C24	79.57 (11)	C27—C22—H221	108.0
C21—Ru1—C24	37.60 (11)	C30—C22—H221	107.9
Ru1—N4—N6	135.48 (17)	C17—C23—C28	120.1 (3)
Ru1—N4—C9	115.74 (18)	C17—C23—H231	119.5
N6—N4—C9	108.6 (2)	C28—C23—H231	120.3
Ru1—N5—C11	125.85 (19)	Ru1—C24—C21	71.89 (15)
Ru1—N5—C13	116.14 (17)	Ru1—C24—C14	70.97 (15)
C11—N5—C13	117.8 (2)	C21—C24—C14	121.0 (3)
N4—N6—C12	106.0 (2)	Ru1—C24—H241	123.9
C9—N7—C12	105.0 (2)	C21—C24—H241	120.0
C9—N7—H71	127.5 (12)	C14—C24—H241	118.6
C12—N7—H71	127.5 (12)	C18—C25—C28	120.0 (3)
Ru1—C8—C14	70.11 (16)	C18—C25—H251	120.5
Ru1—C8—C16	69.50 (16)	C28—C25—H251	119.5
C14—C8—C16	116.6 (3)	C17—C26—C18	120.0 (3)
Ru1—C8—C22	131.5 (2)	C17—C26—H261	120.6
C14—C8—C22	123.8 (3)	C18—C26—H261	119.4
C16—C8—C22	119.6 (3)	C22—C27—H271	109.8
N7—C9—N4	109.8 (2)	C22—C27—H272	109.7
N7—C9—C13	130.9 (2)	H271—C27—H272	108.0
N4—C9—C13	119.2 (2)	C22—C27—H273	111.2
Ru1—C10—C16	71.00 (16)	H271—C27—H273	109.1
Ru1—C10—C21	71.64 (15)	H272—C27—H273	109.0
C16—C10—C21	120.7 (3)	C23—C28—C25	120.2 (3)
Ru1—C10—H101	122.9	C23—C28—H281	119.8
C16—C10—H101	120.0	C25—C28—H281	120.0
C21—C10—H101	118.8	C21—C29—H291	110.7
N5—C11—C20	122.1 (3)	C21—C29—H293	108.3
N5—C11—H111	118.9	H291—C29—H293	109.8
C20—C11—H111	119.0	C21—C29—H292	110.6
N7—C12—N6	110.7 (2)	H291—C29—H292	109.1
N7—C12—C17	124.4 (2)	H293—C29—H292	108.3
N6—C12—C17	124.9 (2)	C22—C30—H301	110.0
C9—C13—N5	111.6 (2)	C22—C30—H303	109.2
C9—C13—C15	125.5 (2)	H301—C30—H303	109.5
N5—C13—C15	122.8 (2)	C22—C30—H302	109.4
Ru1—C14—C8	72.71 (16)	H301—C30—H302	109.3
Ru1—C14—C24	71.41 (15)	H303—C30—H302	109.5
C8—C14—C24	122.1 (3)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N7—H71···Cl3	0.85	2.15	2.984	169

References

Agilent (2014). CrysAlis PRO. Agilent Technologies Ltd, Yarnton, England. Google Scholar
Betteridge, P. W., Carruthers, J. R., Cooper, R. I., Prout, K. & Watkin, D. J. (2003). J. Appl. Cryst. 36, 1487. Web of Science CrossRef IUCr Journals Google Scholar
Flack, H. D. (1983). Acta Cryst. A39, 876–881. CrossRef CAS Web of Science IUCr Journals Google Scholar
Gupta, G., Prasad, K. T., Das, B. & Rao, K. M. (2010). Polyhedron, 29, 904–910. CSD CrossRef CAS Google Scholar
Gupta, G., Therrien, B., Park, S., Lee, S. S. & Kim, J. (2012). J. Coord. Chem. 65, 2523–2534. CSD CrossRef CAS Google Scholar
Hohloch, S., Suntrup, L. & Sarkar, B. (2013). Organometallics, 32, 7376–7385. CSD CrossRef CAS Google Scholar
Macrae, C. F., Edgington, P. R., McCabe, P., Pidcock, E., Shields, G. P., Taylor, R., Towler, M. & van de Streek, J. (2006). J. Appl. Cryst. 39, 453–457. Web of Science CSD CrossRef CAS IUCr Journals Google Scholar
Otwinowski, Z. & Minor, W. (1997). Methods in Enzymology, Vol. 276, Macromolecular Crystallography, Part A, edited by C. W. Carter Jr & R. M. Sweet, pp. 307–326. New York: Academic Press. Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar
Steed, J. W. & Atwood, J. L. (2009). Supramolecular Chemistry. Chichester: John Wiley & Sons. Google Scholar
Süss-Fink, G. (2010). Dalton Trans. 39, 1673–1688. Web of Science PubMed Google Scholar
Westrip, S. P. (2010). J. Appl. Cryst. 43, 920–925. Web of Science CrossRef CAS IUCr Journals Google Scholar

This is an open-access article distributed under the terms of the Creative Commons Attribution (CC-BY) Licence, which permits unrestricted use, distribution, and reproduction in any medium, provided the original authors and source are cited.