(η6-Benzene)(2,2′-bipyridine-κ2N,N′)chloridoruthenium(II) chloride methanol sesquisolvate

Polson, M.I.J.

doi:10.1107/S1600536807066858

metal-organic compounds

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Volume 64| Part 1| January 2008| Page m256

https://doi.org/10.1107/S1600536807066858

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(η⁶-Benzene)(2,2′-bipyridine-κ²N,N′)chloridoruthenium(II) chloride methanol sesquisolvate

Matthew I. J. Polson ^a ^*

^aChemistry Department, University of Canterbury, PO Box 4800, Christchurch, New Zealand
^*Correspondence e-mail: matthew.polson@canterbury.ac.nz

(Received 9 November 2007; accepted 13 December 2007; online 21 December 2007)

In the title compound, [RuCl(C₆H₆)(C₁₀H₈N₂)]Cl·1.5CH₄O, the Ru^II atom is in a distorted octahedral environment coordinated by an η⁶-benzene ring, a chelating 2,2′-bipyridine ligand and a chloride ion. The asymmetric unit is completed by a chloride anion and two methanol molecules, one of which is disordered about a centre of inversion with an occupancy of 0.5. It is an example of a ruthenium complex with a less sterically congested environment than in similar derivatives. In the crystal structure, O—H⋯Cl hydrogen bonds, together with π–π stacking interactions [centroid–centroid distances of 3.472Å(2) Å], stabilize the structure.

Related literature

For literature concerning the synthesis of this class of compound, see Freedman et al. (2001 ). For related structures, see Himeda et al. (2007 ); Lalrempuia & Kollipara (2003 ).

Experimental

Crystal data

[RuCl(C₆H₆)(C₁₀H₈N₂)]Cl·1.5CH₄O
M_r = 454.33
Triclinic, $[P \overline 1]$
a = 6.9027 (11) Å
b = 10.2346 (16) Å
c = 12.895 (2) Å
α = 85.597 (2)°
β = 84.531 (2)°
γ = 75.875 (2)°
V = 878.1 (2) Å³
Z = 2
Mo Kα radiation
μ = 1.21 mm⁻¹
T = 93 (2) K
0.36 × 0.34 × 0.13 mm

Data collection

Bruker APEXII CCD area-detector diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2007 ) T_min = 0.660, T_max = 0.854
4385 measured reflections
3082 independent reflections
2867 reflections with I > 2σ(I)
R_int = 0.014

Refinement

R[F² > 2σ(F²)] = 0.033
wR(F²) = 0.086
S = 1.06
3082 reflections
220 parameters
H-atom parameters constrained
Δρ_max = 1.13 e Å⁻³
Δρ_min = −0.69 e Å⁻³

Table 1
Selected geometric parameters (Å, °)

Ru1—N1	2.083 (3)
Ru1—N2	2.084 (3)
Ru1—C1	2.165 (4)
Ru1—C6	2.186 (4)
Ru1—C5	2.193 (4)
Ru1—C2	2.198 (4)
Ru1—C4	2.198 (4)
Ru1—C3	2.199 (4)
Ru1—Cl1	2.4105 (9)

N1—Ru1—N2	77.18 (11)
N1—Ru1—Cl1	84.01 (8)
N2—Ru1—Cl1	86.34 (8)

Table 2
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O51—H51⋯Cl2	0.84	2.18	3.013 (4)	170
O61—H61⋯Cl2	0.84	2.15	2.986 (6)	171

Data collection: APEX2 (Bruker, 2007); cell refinement: SAINT (Bruker, 2007); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997 ); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997 ) and Mercury (Macrae et al., 2006 ); software used to prepare material for publication: publCIF (Westrip, 2008 ).

Supporting information

Crystal structure: contains datablocks global, I. DOI: https://doi.org/10.1107/S1600536807066858/sj2425sup1.cif

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S1600536807066858/sj2425Isup2.hkl

checkCIF report

Comment top

The desire for a ruthenium complex which could be used to synthesize facially coordinated complexes led to the preparation of the starting material (1) (Freedman et al. 2001). It is convenient to use, in that the benzene ring can be readily removed in a photolytic reaction leaving ruthenium with three, vacant, facially arranged coordination sites. The Ru^II atom is in a distorted octahedral environment, Table 1, coordinating to an η⁶-benzene ring, a chelating 2,2'-bipyridine ligand and a chloride anion. Compared to other similar complexes from the literature, the cation is less bulky both around the benzene ring (Himeda et al., 2007) and in the bipyridine unit (Lalrempuia & Kollipara, 2003). This manifests itself in two angles. The angles between the mean plane of the bipyridine ligand and the mean plane of the benzene ring (60.47 (18)° in 1) become smaller as the ligands become larger due to additional substitution by methyl groups. This forces the two ligands become more parallel to each other. This effect is seen when either the bipyridine (32.24 ° Lalrempuia & Kollipara, 2003) or the benzene ring (36.04° Himeda et al. 2007) is larger due to additional substitution. With the smaller unsubstituted ligands of (1) the ruthenium atom is also more able to sit in the same plane as the bipyridine ligand, lying only 0.075 (1) Å above the plane in the direction of the choride ligand. The methanol solvate molecules form O—H···Cl hydrogen bonds to the chloride anion, Table 2, with D–H A distances of 3.013 (4) Å (O51–Cl2) and 2.986 (6) Å (O61–Cl2). The structure is further stabilized by offset π—π stacking interactions between adjacent N1, C7···C11 rings of the bipyridine ligands, with centroid to centroid distances of 3.472 (2) Å, related by the symmetry operation 1 - x, 1 - y, 1 - z, Fig. 2.

Related literature top

For literature concerning the synthesis of this class of compound, see Freedman et al. (2001). For related structures, see Himeda et al. (2007); Lalrempuia & Kollipara (2003).

Experimental top

The complex was prepared according to literature procedures (Freedman et al. 2001). X-ray quality crystals were grown by slow evaporation of a solution in methanol.

Structure description top

For literature concerning the synthesis of this class of compound, see Freedman et al. (2001). For related structures, see Himeda et al. (2007); Lalrempuia & Kollipara (2003).

Computing details top

Data collection: APEX2 (Bruker, 2007); cell refinement: SAINT (Bruker, 2007); data reduction: SAINT (Bruker, 2007); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997) and Mercury (Bruno et al., 2002); software used to prepare material for publication: publCIF (Westrip, 2008).

Figures top

	Fig. 1. The molecular structure of (1), showing displacement ellipsoids at the 50% probability level.
	Fig. 2. A packing diagram showing the π stacking. The close centroid-centroid approach is shown as a dashed line.

(η⁶-Benzene)(2,2'-bipyridine-κ²N,N')chloridoruthenium(II) chloride methanol sesquisolvate top

Crystal data top

[RuCl(C₆H₆)(C₁₀H₈N₂)]Cl·1.5CH₄O	Z = 2
M_r = 454.33	F(000) = 458
Triclinic, P1	D_x = 1.718 Mg m⁻³
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 6.9027 (11) Å	Cell parameters from 3474 reflections
b = 10.2346 (16) Å	θ = 2.5–26.4°
c = 12.895 (2) Å	µ = 1.21 mm⁻¹
α = 85.597 (2)°	T = 93 K
β = 84.531 (2)°	Block, yellow
γ = 75.875 (2)°	0.36 × 0.34 × 0.13 mm
V = 878.1 (2) Å³

Data collection top

Bruker APEXII CCD area-detector diffractometer	3082 independent reflections
Radiation source: sealed tube	2867 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.014
φ and ω scans	θ_max = 25.1°, θ_min = 2.5°
Absorption correction: multi-scan (SADABS; Bruker, 2007)	h = −8→8
T_min = 0.660, T_max = 0.854	k = −12→12
4385 measured reflections	l = −15→10

Refinement top

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) = 0.086	H-atom parameters constrained
S = 1.06	w = 1/[σ²(F_o²) + (0.0562P)² + 0.5007P] where P = (F_o² + 2F_c²)/3
3082 reflections	(Δ/σ)_max < 0.001
220 parameters	Δρ_max = 1.13 e Å⁻³
0 restraints	Δρ_min = −0.69 e Å⁻³

Crystal data top

[RuCl(C₆H₆)(C₁₀H₈N₂)]Cl·1.5CH₄O	γ = 75.875 (2)°
M_r = 454.33	V = 878.1 (2) Å³
Triclinic, P1	Z = 2
a = 6.9027 (11) Å	Mo Kα radiation
b = 10.2346 (16) Å	µ = 1.21 mm⁻¹
c = 12.895 (2) Å	T = 93 K
α = 85.597 (2)°	0.36 × 0.34 × 0.13 mm
β = 84.531 (2)°

Data collection top

Bruker APEXII CCD area-detector diffractometer	3082 independent reflections
Absorption correction: multi-scan (SADABS; Bruker, 2007)	2867 reflections with I > 2σ(I)
T_min = 0.660, T_max = 0.854	R_int = 0.014
4385 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.033	0 restraints
wR(F²) = 0.086	H-atom parameters constrained
S = 1.06	Δρ_max = 1.13 e Å⁻³
3082 reflections	Δρ_min = −0.69 e Å⁻³
220 parameters

Special details top

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.

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

	x	y	z	U_iso*/U_eq	Occ. (<1)
Ru1	0.60854 (4)	0.67682 (3)	0.77268 (2)	0.02474 (11)
Cl1	0.89451 (12)	0.76724 (9)	0.71514 (7)	0.0277 (2)
Cl2	0.12633 (18)	0.29047 (14)	0.82005 (9)	0.0536 (3)
N1	0.6736 (4)	0.5821 (3)	0.6319 (2)	0.0217 (6)
N2	0.4510 (4)	0.8207 (3)	0.6686 (2)	0.0244 (6)
C7	0.6008 (5)	0.6559 (3)	0.5465 (2)	0.0201 (7)
C12	0.4677 (5)	0.7878 (3)	0.5677 (3)	0.0217 (7)
C2	0.4713 (8)	0.7559 (5)	0.9230 (3)	0.0530 (13)
H2	0.4272	0.8559	0.9289	0.064*
C1	0.3440 (7)	0.6888 (5)	0.8796 (3)	0.0463 (11)
H1	0.2101	0.7407	0.8579	0.056*
C6	0.4177 (8)	0.5533 (5)	0.8541 (3)	0.0499 (13)
H6	0.3375	0.5085	0.8140	0.060*
C3	0.6688 (8)	0.6925 (6)	0.9351 (3)	0.0557 (14)
H3	0.7634	0.7478	0.9496	0.067*
C4	0.7456 (8)	0.5604 (6)	0.9086 (3)	0.0515 (12)
H4	0.8939	0.5224	0.9047	0.062*
C5	0.6250 (8)	0.4896 (5)	0.8699 (3)	0.0489 (12)
H5	0.6880	0.4012	0.8385	0.059*
C11	0.7918 (5)	0.4575 (3)	0.6204 (3)	0.0234 (7)
H11	0.8430	0.4054	0.6803	0.028*
C8	0.6504 (5)	0.6079 (3)	0.4470 (2)	0.0220 (7)
H8	0.6023	0.6628	0.3876	0.026*
C9	0.7708 (5)	0.4794 (4)	0.4354 (3)	0.0232 (7)
H9	0.8048	0.4442	0.3682	0.028*
C10	0.8406 (5)	0.4030 (4)	0.5234 (3)	0.0236 (7)
H10	0.9215	0.3140	0.5174	0.028*
C14	0.2393 (5)	0.9964 (4)	0.5210 (3)	0.0307 (8)
H14	0.1655	1.0562	0.4708	0.037*
C13	0.3616 (5)	0.8737 (4)	0.4923 (3)	0.0255 (7)
H13	0.3729	0.8485	0.4222	0.031*
C16	0.3322 (5)	0.9412 (4)	0.6948 (3)	0.0307 (8)
H16	0.3216	0.9650	0.7652	0.037*
C15	0.2259 (5)	1.0307 (4)	0.6237 (3)	0.0337 (9)
H15	0.1444	1.1150	0.6447	0.040*
O51	0.5683 (5)	0.2257 (4)	0.7539 (3)	0.0553 (8)
H51	0.4459	0.2334	0.7716	0.083*
C50	0.6807 (7)	0.1122 (5)	0.8067 (4)	0.0484 (11)
H50A	0.5976	0.0837	0.8658	0.073*
H50B	0.7973	0.1347	0.8322	0.073*
H50C	0.7261	0.0388	0.7590	0.073*
O61	0.1958 (9)	0.0351 (6)	0.9544 (5)	0.0413 (13)*	0.50
H61	0.1872	0.1092	0.9201	0.062*	0.50
C60	−0.002 (4)	0.035 (3)	1.016 (2)	0.135 (8)*	0.50
H60A	0.0149	0.0364	1.0909	0.202*	0.50
H60B	−0.0448	−0.0459	1.0032	0.202*	0.50
H60C	−0.1028	0.1156	0.9950	0.202*	0.50

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Ru1	0.02860 (18)	0.03351 (18)	0.01564 (16)	−0.01396 (12)	−0.00330 (11)	−0.00015 (11)
Cl1	0.0235 (4)	0.0287 (4)	0.0335 (5)	−0.0100 (3)	−0.0057 (3)	−0.0006 (3)
Cl2	0.0509 (7)	0.0718 (8)	0.0416 (6)	−0.0182 (6)	−0.0168 (5)	0.0028 (5)
N1	0.0215 (14)	0.0283 (15)	0.0187 (13)	−0.0131 (12)	−0.0036 (11)	0.0024 (11)
N2	0.0206 (14)	0.0305 (16)	0.0246 (15)	−0.0109 (12)	−0.0005 (11)	−0.0024 (12)
C7	0.0175 (16)	0.0258 (17)	0.0203 (16)	−0.0120 (13)	−0.0044 (12)	0.0032 (13)
C12	0.0176 (16)	0.0281 (17)	0.0231 (16)	−0.0140 (14)	−0.0012 (13)	0.0022 (13)
C2	0.072 (3)	0.064 (3)	0.028 (2)	−0.031 (3)	0.017 (2)	−0.015 (2)
C1	0.041 (2)	0.076 (3)	0.0229 (19)	−0.021 (2)	0.0037 (17)	0.008 (2)
C6	0.073 (3)	0.081 (3)	0.0145 (18)	−0.058 (3)	−0.0018 (19)	0.0070 (19)
C3	0.065 (3)	0.099 (4)	0.0178 (19)	−0.046 (3)	−0.0041 (19)	−0.006 (2)
C4	0.054 (3)	0.085 (4)	0.0195 (19)	−0.027 (3)	−0.0085 (19)	0.016 (2)
C5	0.074 (3)	0.048 (3)	0.022 (2)	−0.020 (2)	0.007 (2)	0.0148 (18)
C11	0.0226 (17)	0.0259 (17)	0.0242 (17)	−0.0112 (14)	−0.0059 (13)	0.0049 (13)
C8	0.0191 (16)	0.0318 (18)	0.0176 (16)	−0.0122 (14)	−0.0039 (12)	0.0046 (13)
C9	0.0179 (16)	0.0344 (19)	0.0217 (16)	−0.0140 (14)	−0.0014 (13)	−0.0033 (14)
C10	0.0167 (16)	0.0267 (17)	0.0298 (18)	−0.0096 (14)	−0.0039 (13)	0.0007 (14)
C14	0.0183 (17)	0.0299 (19)	0.046 (2)	−0.0122 (15)	−0.0043 (15)	0.0085 (16)
C13	0.0214 (17)	0.0291 (18)	0.0296 (18)	−0.0138 (14)	−0.0050 (14)	0.0045 (14)
C16	0.0263 (19)	0.036 (2)	0.0326 (19)	−0.0139 (16)	0.0049 (15)	−0.0091 (16)
C15	0.0213 (18)	0.0283 (19)	0.051 (2)	−0.0086 (15)	0.0045 (16)	−0.0028 (17)
O51	0.063 (2)	0.058 (2)	0.0437 (18)	−0.0138 (17)	−0.0090 (16)	0.0107 (15)
C50	0.048 (3)	0.042 (2)	0.054 (3)	−0.010 (2)	−0.012 (2)	0.005 (2)

Geometric parameters (Å, º) top

Ru1—N1	2.083 (3)	C4—H4	1.0000
Ru1—N2	2.084 (3)	C5—H5	1.0000
Ru1—C1	2.165 (4)	C11—C10	1.387 (5)
Ru1—C6	2.186 (4)	C11—H11	0.9500
Ru1—C5	2.193 (4)	C8—C9	1.385 (5)
Ru1—C2	2.198 (4)	C8—H8	0.9500
Ru1—C4	2.198 (4)	C9—C10	1.384 (5)
Ru1—C3	2.199 (4)	C9—H9	0.9500
Ru1—Cl1	2.4105 (9)	C10—H10	0.9500
N1—C11	1.346 (4)	C14—C15	1.385 (6)
N1—C7	1.352 (4)	C14—C13	1.386 (5)
N2—C16	1.351 (5)	C14—H14	0.9500
N2—C12	1.356 (4)	C13—H13	0.9500
C7—C8	1.392 (5)	C16—C15	1.374 (6)
C7—C12	1.464 (5)	C16—H16	0.9500
C12—C13	1.394 (5)	C15—H15	0.9500
C2—C3	1.378 (8)	O51—C50	1.398 (6)
C2—C1	1.417 (7)	O51—H51	0.8400
C2—H2	1.0000	C50—H50A	0.9800
C1—C6	1.408 (7)	C50—H50B	0.9800
C1—H1	1.0000	C50—H50C	0.9800
C6—C5	1.447 (7)	O61—C60	1.51 (3)
C6—H6	1.0000	O61—H61	0.8400
C3—C4	1.383 (8)	C60—H60A	0.9800
C3—H3	1.0000	C60—H60B	0.9800
C4—C5	1.378 (7)	C60—H60C	0.9800

N1—Ru1—N2	77.18 (11)	C1—C6—Ru1	70.3 (2)
N1—Ru1—C1	127.42 (15)	C5—C6—Ru1	70.9 (2)
N2—Ru1—C1	91.75 (15)	C1—C6—H6	120.4
N1—Ru1—C6	99.21 (14)	C5—C6—H6	120.4
N2—Ru1—C6	111.47 (16)	Ru1—C6—H6	120.4
C1—Ru1—C6	37.76 (19)	C2—C3—C4	120.9 (5)
N1—Ru1—C5	94.95 (14)	C2—C3—Ru1	71.7 (2)
N2—Ru1—C5	148.17 (16)	C4—C3—Ru1	71.6 (2)
C1—Ru1—C5	68.40 (19)	C2—C3—H3	119.0
C6—Ru1—C5	38.58 (19)	C4—C3—H3	119.0
N1—Ru1—C2	165.29 (15)	Ru1—C3—H3	119.0
N2—Ru1—C2	101.06 (17)	C5—C4—C3	120.4 (5)
C1—Ru1—C2	37.89 (18)	C5—C4—Ru1	71.5 (2)
C6—Ru1—C2	67.59 (18)	C3—C4—Ru1	71.7 (3)
C5—Ru1—C2	78.80 (19)	C5—C4—H4	119.3
N1—Ru1—C4	116.02 (17)	C3—C4—H4	119.3
N2—Ru1—C4	166.80 (17)	Ru1—C4—H4	119.3
C1—Ru1—C4	80.20 (18)	C4—C5—C6	120.4 (5)
C6—Ru1—C4	68.00 (18)	C4—C5—Ru1	71.9 (3)
C5—Ru1—C4	36.57 (19)	C6—C5—Ru1	70.5 (2)
C2—Ru1—C4	66.2 (2)	C4—C5—H5	119.1
N1—Ru1—C3	151.14 (18)	C6—C5—H5	119.1
N2—Ru1—C3	130.37 (18)	Ru1—C5—H5	119.1
C1—Ru1—C3	67.60 (18)	N1—C11—C10	121.8 (3)
C6—Ru1—C3	79.73 (17)	N1—C11—H11	119.1
C5—Ru1—C3	66.1 (2)	C10—C11—H11	119.1
C2—Ru1—C3	36.5 (2)	C9—C8—C7	119.3 (3)
C4—Ru1—C3	36.7 (2)	C9—C8—H8	120.4
N1—Ru1—Cl1	84.01 (8)	C7—C8—H8	120.4
N2—Ru1—Cl1	86.34 (8)	C10—C9—C8	118.8 (3)
C1—Ru1—Cl1	147.23 (14)	C10—C9—H9	120.6
C6—Ru1—Cl1	162.19 (14)	C8—C9—H9	120.6
C5—Ru1—Cl1	123.93 (14)	C9—C10—C11	119.6 (3)
C2—Ru1—Cl1	110.55 (13)	C9—C10—H10	120.2
C4—Ru1—Cl1	94.76 (13)	C11—C10—H10	120.2
C3—Ru1—Cl1	89.00 (13)	C15—C14—C13	119.2 (3)
C11—N1—C7	119.0 (3)	C15—C14—H14	120.4
C11—N1—Ru1	124.3 (2)	C13—C14—H14	120.4
C7—N1—Ru1	116.5 (2)	C14—C13—C12	119.1 (3)
C16—N2—C12	118.5 (3)	C14—C13—H13	120.4
C16—N2—Ru1	125.0 (2)	C12—C13—H13	120.4
C12—N2—Ru1	116.5 (2)	N2—C16—C15	122.7 (3)
N1—C7—C8	121.6 (3)	N2—C16—H16	118.6
N1—C7—C12	114.8 (3)	C15—C16—H16	118.6
C8—C7—C12	123.6 (3)	C16—C15—C14	119.0 (3)
N2—C12—C13	121.4 (3)	C16—C15—H15	120.5
N2—C12—C7	114.6 (3)	C14—C15—H15	120.5
C13—C12—C7	124.0 (3)	C50—O51—H51	109.5
C3—C2—C1	120.7 (5)	O51—C50—H50A	109.5
C3—C2—Ru1	71.8 (3)	O51—C50—H50B	109.5
C1—C2—Ru1	69.8 (2)	H50A—C50—H50B	109.5
C3—C2—H2	118.9	O51—C50—H50C	109.5
C1—C2—H2	118.9	H50A—C50—H50C	109.5
Ru1—C2—H2	118.9	H50B—C50—H50C	109.5
C6—C1—C2	119.4 (5)	C60—O61—H61	109.5
C6—C1—Ru1	71.9 (2)	O61—C60—H60A	109.5
C2—C1—Ru1	72.3 (2)	O61—C60—H60B	109.5
C6—C1—H1	120.0	H60A—C60—H60B	109.5
C2—C1—H1	120.0	O61—C60—H60C	109.5
Ru1—C1—H1	120.0	H60A—C60—H60C	109.5
C1—C6—C5	118.2 (4)	H60B—C60—H60C	109.5

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O51—H51···Cl2	0.84	2.18	3.013 (4)	170
O61—H61···Cl2	0.84	2.15	2.986 (6)	171

Experimental details

Crystal data
Chemical formula	[RuCl(C₆H₆)(C₁₀H₈N₂)]Cl·1.5CH₄O
M_r	454.33
Crystal system, space group	Triclinic, P1
Temperature (K)	93
a, b, c (Å)	6.9027 (11), 10.2346 (16), 12.895 (2)
α, β, γ (°)	85.597 (2), 84.531 (2), 75.875 (2)
V (Å³)	878.1 (2)
Z	2
Radiation type	Mo Kα
µ (mm⁻¹)	1.21
Crystal size (mm)	0.36 × 0.34 × 0.13

Data collection
Diffractometer	Bruker APEXII CCD area-detector
Absorption correction	Multi-scan (SADABS; Bruker, 2007)
T_min, T_max	0.660, 0.854
No. of measured, independent and observed [I > 2σ(I)] reflections	4385, 3082, 2867
R_int	0.014
(sin θ/λ)_max (Å⁻¹)	0.596

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.033, 0.086, 1.06
No. of reflections	3082
No. of parameters	220
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	1.13, −0.69

Computer programs: APEX2 (Bruker, 2007), SAINT (Bruker, 2007), SHELXS97 (Sheldrick, 1997), SHELXL97 (Sheldrick, 1997), ORTEP-3 for Windows (Farrugia, 1997) and Mercury (Bruno et al., 2002), publCIF (Westrip, 2008).

Selected geometric parameters (Å, º) top

Ru1—N1	2.083 (3)	Ru1—C2	2.198 (4)
Ru1—N2	2.084 (3)	Ru1—C4	2.198 (4)
Ru1—C1	2.165 (4)	Ru1—C3	2.199 (4)
Ru1—C6	2.186 (4)	Ru1—Cl1	2.4105 (9)
Ru1—C5	2.193 (4)

N1—Ru1—N2	77.18 (11)	N2—Ru1—Cl1	86.34 (8)
N1—Ru1—Cl1	84.01 (8)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O51—H51···Cl2	0.84	2.18	3.013 (4)	170.0
O61—H61···Cl2	0.84	2.15	2.986 (6)	170.5

Acknowledgements

The author acknowledges the extensive advice of Professor Peter Steel and funding from the New Zealand Foundation of Research, Science and Technology.

References

Bruker (2007). APEX2 (Version 2.1-4), SAINT (Version 7.34A) and SADABS (Version 2004/1). Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
Farrugia, L. J. (1997). J. Appl. Cryst. 30, 565. CrossRef IUCr Journals Google Scholar
Freedman, D. A., Evju, J. K., Pomije, M. K. & Mann, K. R. (2001). Inorg. Chem. 40, 5711–5715. Web of Science CrossRef PubMed CAS Google Scholar
Himeda, Y., Onozawa-Komatsuzaki, N., Sugihara, H. & Kasuga, K. (2007). Organometallics, 26, 702–712. Web of Science CSD CrossRef CAS Google Scholar
Lalrempuia, R. & Kollipara, M. R. (2003). Polyhedron, 22, 3155–3160. Web of Science 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
Sheldrick, G. M. (1997). SHELXS97 and SHELXL97. University of Göttingen, Germany. Google Scholar
Westrip, S. P. (2008). publCIF. In preparation. Google Scholar

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