Chlorido­(η6-p-cymene)[6-(2-hydroxy­phen­yl)-2,2′-bipyridine]­ruthenium(II) chloride chloro­form solvate

Zhou, H.-F.; Bian, Z.-Q.; Liu, Z.-W.; Huang, C.-H.; Zhao, Y.-L.

doi:10.1107/S1600536807023975

Buy article online - an online subscription or single-article purchase is required to access this article.

Chlorido(η⁶-p-cymene)[6-(2-hydroxyphenyl)-2,2′-bipyridine]ruthenium(II) chloride chloroform solvate

H.-F. Zhou, Z.-Q. Bian, Z.-W. Liu, C.-H. Huang and Y.-L. Zhao

The title compound, [RuCl(C₁₀H₁₄)(C₁₆H₁₂N₂O)]Cl·CHCl₃, has been synthesized by the reaction of [RuCl₂(p-cymene)]₂ with 6-(2-hydroxyphenyl)-2,2′-bipyridine in acetonitrile. The Ru^II cation is in a pseudo-octahedral environment formed by a chloride anion, a cymene molecule (with an η⁶ coordination mode) and a chelating 6-(2-hydroxyphenyl)-2,2′-bipyridine ligand. The other chloride anion is uncoordinated but links with the complex via O—H

Cl hydrogen bonding. The two methyl groups of the isopropyl group are disordered over two positions in approximately a 0.7:0.3 ratio.

Read article Similar articles

Supporting information

	Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536807023975/xu2245sup1.cif Contains datablocks I, global
	Structure factor file (CIF format) https://doi.org/10.1107/S1600536807023975/xu2245Isup2.hkl Contains datablock I

CCDC reference: 621429

checkCIF report

Key indicators

Single-crystal X-ray study
T = 113 K
Mean (C-C) = 0.003 Å
Disorder in main residue
R factor = 0.026
wR factor = 0.064
Data-to-parameter ratio = 18.2

checkCIF/PLATON results

No syntax errors found



Alert level C
PLAT062_ALERT_4_C Rescale T(min) & T(max) by .....................       0.99
PLAT220_ALERT_2_C Large Non-Solvent    C     Ueq(max)/Ueq(min) ...       3.41 Ratio
PLAT222_ALERT_3_C Large Non-Solvent    H     Ueq(max)/Ueq(min) ...       3.15 Ratio
PLAT301_ALERT_3_C Main Residue  Disorder .........................       6.00 Perc.

Alert level G
PLAT860_ALERT_3_G Note: Number of Least-Squares Restraints .......         48

   0 ALERT level A = In general: serious problem
   0 ALERT level B = Potentially serious problem
   4 ALERT level C = Check and explain
   1 ALERT level G = General alerts; check

   0 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
   1 ALERT type 2 Indicator that the structure model may be wrong or deficient
   3 ALERT type 3 Indicator that the structure quality may be low
   1 ALERT type 4 Improvement, methodology, query or suggestion
   0 ALERT type 5 Informative message, check

Comment top

The complex consists of [RuCl(C₁₀H₁₄)(C₁₆H₁₁N₂OH)]⁺ cation, the charge being balanced by one interstitial chloride anion. The metal center ruthenium ion is coordinated by a chloride anion, a 6-(2-hydroxyphenyl)-2,2'-bipyridine (hpbipy) ligand linked in a bidentate manner through its two N atoms, defining a five-membered chelate ring, and the arene ring linked through its π-cloud in a η⁶ manner (see Fig. 1). The complex crystallizes in the triclinic space group. The geometry around the metal atom is best described as a distorted octahedron, the benzene ring occupying three sites of octahedral coordination geometry, the Cl^- anion and the two pyridine N atoms occupying the other three sites of octahedral geometry. The distortion of the octahedral geometry is evident from the values of the N1—Ru1—N2, Cl1—Ru1—N1 and Cl1—Ru1—N2 angles (Table 1). In hpbipy there is a torsion angle of 2.7 (2)° between the two pyridyl rings and there is one of 113.5 (2)° between the central pyridine ring and the phenolate ring, which is typical behavior for mixed pyridine-phenol ligand and occurs because the phenolate lone pair is not in the same plane as the adjacent pyridyl ring (Bardwell et al., 1996). In the other ligand, the p-cymene ring is almost planar. The Ru—C distances are almost equal, and Ru to p-cymene ring centroid distance agrees well with those found in other (p-cymene) ruthenium (II) complexes, for example, C₁₉H₂₆F₆IN₄PRu and C₂₀H₂₈ClF₆N₄PRu described by Poyatos et al., (2004). Defining X as the centroid of the arene ring, the Cl1—Ru1-X, N1—Ru1-X and N2—Ru1-X angles are 129.07 (3)°, 128.97 (6)° and 132.85 (5)°, respectively. It is the flexibility of the pyridine ligand that makes possible a near equal distribution of the N, N, and Cl donor atoms around the p-cymene ring.

The non-coordinated chloride anion is linked, via O—H···Cl hydrogen bonding, with the pyridine-phenol ligand (Table 2 and Fig. 2), leading the parallel supra-molecular chain.

Related literature top

For related structures, see: Bardwell et al. (1996); Poyatos et al. (2004). For synthesis, see: Jeffery et al. (1992).

Experimental top

6-(2-Hydroxyphenyl)-2,2'-bipyridine (hpbipy) was prepared according to the literature procedure reported by Jeffery et al. (1992). The complex was prepared using [BzRuCl₂]₂ (0.1225 g, 0.20 mmol) and hpbipy (0.1120 g, 0.23 mmol) dissolved in 50 ml acetonitrile (HPLC grade). The mixture was refluxed with stirring under nitrogen for 10 h. The flask was cooled in an ice bath, a bright orange solid was filtered, washed with small amount of acetonitrile. The solid was dissolved in methanol, then added diethyl ether carefully to get the bright orange precipitate. The precipitate was recrystallized twice yielding bright orange microcrystals (yield 70%). Analysis found: C 51.38%, H 5.28%, N 4.48%; calculated for [RuCl(C₁₀H₁₄)(C₁₆H₁₁N₂OH)]Cl.5H₂O: C 51.70%, H 5.17%, N 4.64%. TOF-MS: m/z = 519 (M—Cl). X-ray quality single crystals were grown by slow evaporation of a CHCl₃ solution.

Structure description top

The non-coordinated chloride anion is linked, via O—H···Cl hydrogen bonding, with the pyridine-phenol ligand (Table 2 and Fig. 2), leading the parallel supra-molecular chain.

For related structures, see: Bardwell et al. (1996); Poyatos et al. (2004). For synthesis, see: Jeffery et al. (1992).

Computing details top

Data collection: CrystalClear (Rigaku, 2000); cell refinement: CrystalClear; data reduction: CrystalClear; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: SHELXTL (Bruker, 1998); software used to prepare material for publication: CrystalStructure (Rigaku/MSC, 2005).

Figures top

	Fig. 1. The molecular structure of (I), showing displacement ellipsoids at the 50% probability level. The CHCl₃ solvent molecules, the free chloride anion and all H atoms have been omitted for clarity.
	Fig. 2. The crystal structure of the complex, showing the hydrogen bond interactions.

[6-(2-Hydroxyphenyl)-2,2'-bipyridine]chloro(η⁶-p-cymene)ruthenium(II) chloride chloroform solvate top

Crystal data top

[RuCl(C₁₀H₁₄)(C₁₆H₁₂N₂O)]Cl·CHCl₃	Z = 2
M_r = 673.83	F(000) = 680
Triclinic, P1	D_x = 1.622 Mg m⁻³
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71070 Å
a = 9.2135 (14) Å	Cell parameters from 4697 reflections
b = 12.8915 (19) Å	θ = 1.7–27.9°
c = 13.527 (2) Å	µ = 1.08 mm⁻¹
α = 105.406 (3)°	T = 113 K
β = 109.022 (2)°	Block, orange
γ = 102.663 (3)°	0.34 × 0.32 × 0.26 mm
V = 1379.4 (4) Å³

Data collection top

Rigaku Saturn diffractometer	6455 independent reflections
Radiation source: rotating anode	5056 reflections with I > 2σ(I)
Confocal monochromator	R_int = 0.032
Detector resolution: 7.31 pixels mm^-1	θ_max = 27.9°, θ_min = 1.7°
ω scans	h = −11→12
Absorption correction: multi-scan (Jacobson, 1998)	k = −16→13
T_min = 0.711, T_max = 0.767	l = −17→17
12987 measured reflections

Refinement top

Refinement on F²	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F² > 2σ(F²)] = 0.026	H atoms treated by a mixture of independent and constrained refinement
wR(F²) = 0.064	w = 1/[σ²(F_o²) + (0.0278P)²] where P = (F_o² + 2F_c²)/3
S = 0.99	(Δ/σ)_max = 0.003
6455 reflections	Δρ_max = 0.50 e Å⁻³
354 parameters	Δρ_min = −0.53 e Å⁻³
48 restraints	Extinction correction: SHELXL97, Fc^*=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.0062 (5)

Crystal data top

[RuCl(C₁₀H₁₄)(C₁₆H₁₂N₂O)]Cl·CHCl₃	γ = 102.663 (3)°
M_r = 673.83	V = 1379.4 (4) Å³
Triclinic, P1	Z = 2
a = 9.2135 (14) Å	Mo Kα radiation
b = 12.8915 (19) Å	µ = 1.08 mm⁻¹
c = 13.527 (2) Å	T = 113 K
α = 105.406 (3)°	0.34 × 0.32 × 0.26 mm
β = 109.022 (2)°

Data collection top

Rigaku Saturn diffractometer	6455 independent reflections
Absorption correction: multi-scan (Jacobson, 1998)	5056 reflections with I > 2σ(I)
T_min = 0.711, T_max = 0.767	R_int = 0.032
12987 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.026	48 restraints
wR(F²) = 0.064	H atoms treated by a mixture of independent and constrained refinement
S = 0.99	Δρ_max = 0.50 e Å⁻³
6455 reflections	Δρ_min = −0.53 e Å⁻³
354 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	0.06609 (2)	0.119648 (12)	0.263140 (13)	0.01230 (6)
Cl1	−0.13959 (6)	0.04881 (4)	0.07590 (4)	0.01967 (12)
Cl2	0.77785 (6)	0.28443 (4)	0.72438 (4)	0.01802 (11)
Cl3	0.77344 (8)	0.26543 (5)	1.01892 (4)	0.03189 (15)
Cl4	0.52444 (8)	0.35538 (5)	0.92069 (6)	0.03474 (15)
Cl5	0.85304 (9)	0.50928 (5)	1.06956 (5)	0.03829 (17)
O1	−0.11761 (19)	0.25455 (12)	0.53521 (12)	0.0195 (3)
H1	−0.135 (3)	0.260 (2)	0.588 (2)	0.035 (8)*
N1	0.1906 (2)	0.22880 (13)	0.20732 (13)	0.0141 (3)
N2	−0.0190 (2)	0.26007 (12)	0.29346 (12)	0.0111 (3)
C1	0.2867 (3)	0.20021 (18)	0.15562 (16)	0.0192 (4)
H1A	0.2904	0.1247	0.1376	0.023*
C2	0.3796 (3)	0.27783 (18)	0.12835 (17)	0.0232 (5)
H2	0.4485	0.2566	0.0935	0.028*
C3	0.3715 (3)	0.38664 (18)	0.15209 (17)	0.0229 (5)
H3	0.4359	0.4415	0.1347	0.027*
C4	0.2684 (3)	0.41545 (17)	0.20171 (16)	0.0184 (4)
H4	0.2589	0.4894	0.2167	0.022*
C5	0.1793 (2)	0.33424 (15)	0.22897 (15)	0.0137 (4)
C6	0.0646 (2)	0.35315 (15)	0.27995 (15)	0.0124 (4)
C7	0.0400 (3)	0.45734 (16)	0.31050 (16)	0.0164 (4)
H7	0.1024	0.5214	0.3027	0.020*
C8	−0.0764 (3)	0.46652 (17)	0.35239 (17)	0.0200 (5)
H8	−0.0935	0.5375	0.3757	0.024*
C9	−0.1676 (3)	0.37102 (16)	0.35989 (17)	0.0178 (4)
H9	−0.2514	0.3754	0.3855	0.021*
C10	−0.1381 (2)	0.26836 (15)	0.33020 (15)	0.0135 (4)
C11	−0.2399 (2)	0.16594 (15)	0.33706 (16)	0.0134 (4)
C12	−0.2287 (2)	0.16362 (16)	0.44268 (16)	0.0141 (4)
C13	−0.3235 (3)	0.06753 (16)	0.44986 (17)	0.0177 (4)
H13	−0.3146	0.0653	0.5212	0.021*
C14	−0.4304 (3)	−0.02437 (16)	0.35292 (18)	0.0192 (4)
H14	−0.4944	−0.0898	0.3579	0.023*
C15	−0.4449 (3)	−0.02147 (16)	0.24794 (18)	0.0197 (5)
H15	−0.5195	−0.0844	0.1816	0.024*
C16	−0.3505 (3)	0.07302 (16)	0.24032 (17)	0.0168 (4)
H16	−0.3611	0.0747	0.1686	0.020*
C17	0.0212 (3)	−0.06009 (17)	0.25867 (19)	0.0227 (5)
C18	−0.0163 (3)	0.00294 (16)	0.34352 (18)	0.0200 (5)
H18	−0.1196	−0.0250	0.3451	0.024*
C19	0.0996 (3)	0.10807 (17)	0.42677 (17)	0.0179 (4)
H19	0.0708	0.1497	0.4824	0.021*
C20	0.2566 (2)	0.15333 (16)	0.43013 (17)	0.0160 (4)
C21	0.2889 (3)	0.08878 (16)	0.34213 (17)	0.0174 (4)
H21	0.3912	0.1169	0.3393	0.021*
C22	0.1741 (3)	−0.01612 (17)	0.25820 (18)	0.0202 (5)
H22	0.2011	−0.0570	0.2011	0.024*
C23	−0.1038 (3)	−0.16856 (17)	0.1673 (2)	0.0352 (6)
H23A	−0.0809	−0.1818	0.1000	0.053*
H23B	−0.2126	−0.1620	0.1496	0.053*
H23C	−0.0995	−0.2327	0.1927	0.053*
C24	0.3834 (3)	0.26317 (17)	0.52252 (17)	0.0221 (5)
H24A	0.4505	0.2432	0.5804	0.026*	0.701 (13)
H24B	0.4704	0.2383	0.5583	0.026*	0.299 (13)
C25	0.3058 (5)	0.3461 (4)	0.5771 (4)	0.0319 (13)	0.701 (13)
H25A	0.2449	0.3092	0.6130	0.048*	0.701 (13)
H25B	0.2317	0.3643	0.5188	0.048*	0.701 (13)
H25C	0.3922	0.4166	0.6335	0.048*	0.701 (13)
C26	0.4940 (8)	0.3301 (5)	0.4811 (6)	0.0210 (12)	0.701 (13)
H26A	0.4284	0.3535	0.4236	0.031*	0.701 (13)
H26B	0.5481	0.2817	0.4490	0.031*	0.701 (13)
H26C	0.5763	0.3980	0.5443	0.031*	0.701 (13)
C25'	0.3291 (14)	0.3035 (12)	0.6121 (10)	0.042 (3)	0.299 (13)
H25D	0.4173	0.3694	0.6742	0.063*	0.299 (13)
H25E	0.3001	0.2421	0.6393	0.063*	0.299 (13)
H25F	0.2337	0.3260	0.5825	0.063*	0.299 (13)
C26'	0.461 (2)	0.3468 (13)	0.4826 (16)	0.032 (4)	0.299 (13)
H26D	0.3882	0.3888	0.4585	0.048*	0.299 (13)
H26E	0.4821	0.3065	0.4192	0.048*	0.299 (13)
H26F	0.5641	0.4005	0.5437	0.048*	0.299 (13)
C27	0.7341 (3)	0.37268 (17)	0.96670 (17)	0.0221 (5)
H27	0.7638	0.3645	0.9009	0.027*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Ru1	0.01053 (9)	0.00951 (8)	0.01572 (9)	0.00345 (6)	0.00411 (6)	0.00437 (6)
Cl1	0.0179 (3)	0.0177 (2)	0.0158 (2)	0.00578 (19)	0.0030 (2)	−0.00029 (18)
Cl2	0.0196 (3)	0.0158 (2)	0.0172 (2)	0.00279 (19)	0.0078 (2)	0.00601 (18)
Cl3	0.0382 (4)	0.0201 (3)	0.0211 (3)	0.0056 (2)	−0.0036 (2)	0.0061 (2)
Cl4	0.0265 (3)	0.0342 (3)	0.0495 (4)	0.0095 (3)	0.0160 (3)	0.0240 (3)
Cl5	0.0524 (5)	0.0186 (3)	0.0234 (3)	−0.0026 (3)	0.0025 (3)	0.0049 (2)
O1	0.0203 (9)	0.0178 (8)	0.0148 (8)	−0.0013 (6)	0.0077 (7)	0.0033 (6)
N1	0.0145 (9)	0.0141 (8)	0.0118 (8)	0.0038 (7)	0.0044 (7)	0.0040 (6)
N2	0.0110 (8)	0.0087 (7)	0.0085 (7)	0.0011 (6)	0.0010 (6)	0.0010 (6)
C1	0.0214 (12)	0.0214 (10)	0.0148 (10)	0.0092 (9)	0.0076 (9)	0.0045 (8)
C2	0.0267 (13)	0.0269 (11)	0.0184 (11)	0.0086 (9)	0.0129 (10)	0.0078 (9)
C3	0.0227 (12)	0.0279 (12)	0.0221 (11)	0.0048 (9)	0.0128 (10)	0.0135 (9)
C4	0.0221 (12)	0.0162 (10)	0.0178 (10)	0.0052 (8)	0.0085 (9)	0.0080 (8)
C5	0.0151 (10)	0.0137 (9)	0.0100 (9)	0.0037 (8)	0.0037 (8)	0.0035 (7)
C6	0.0132 (10)	0.0124 (9)	0.0107 (9)	0.0038 (7)	0.0034 (8)	0.0054 (7)
C7	0.0196 (11)	0.0123 (9)	0.0150 (10)	0.0023 (8)	0.0056 (8)	0.0062 (7)
C8	0.0256 (12)	0.0125 (10)	0.0228 (11)	0.0081 (8)	0.0114 (10)	0.0046 (8)
C9	0.0211 (12)	0.0150 (10)	0.0216 (11)	0.0072 (8)	0.0128 (9)	0.0070 (8)
C10	0.0140 (10)	0.0124 (9)	0.0118 (9)	0.0034 (7)	0.0041 (8)	0.0035 (7)
C11	0.0108 (10)	0.0103 (9)	0.0192 (10)	0.0045 (7)	0.0063 (8)	0.0047 (7)
C12	0.0118 (10)	0.0129 (9)	0.0182 (10)	0.0050 (7)	0.0066 (8)	0.0054 (8)
C13	0.0179 (11)	0.0163 (10)	0.0244 (11)	0.0076 (8)	0.0112 (9)	0.0110 (8)
C14	0.0117 (11)	0.0119 (10)	0.0381 (12)	0.0040 (8)	0.0132 (10)	0.0114 (9)
C15	0.0109 (10)	0.0123 (9)	0.0275 (11)	0.0033 (8)	0.0044 (9)	−0.0006 (8)
C16	0.0135 (10)	0.0174 (10)	0.0208 (10)	0.0070 (8)	0.0082 (9)	0.0058 (8)
C17	0.0170 (11)	0.0119 (10)	0.0364 (13)	0.0056 (8)	0.0047 (10)	0.0118 (9)
C18	0.0136 (11)	0.0181 (10)	0.0356 (12)	0.0068 (8)	0.0101 (10)	0.0196 (9)
C19	0.0174 (11)	0.0223 (10)	0.0199 (10)	0.0095 (8)	0.0075 (9)	0.0146 (8)
C20	0.0119 (10)	0.0187 (10)	0.0191 (10)	0.0065 (8)	0.0032 (8)	0.0123 (8)
C21	0.0114 (10)	0.0175 (10)	0.0278 (11)	0.0085 (8)	0.0073 (9)	0.0129 (8)
C22	0.0190 (12)	0.0144 (10)	0.0304 (12)	0.0118 (8)	0.0098 (10)	0.0085 (9)
C23	0.0208 (13)	0.0124 (10)	0.0574 (17)	0.0045 (9)	0.0029 (12)	0.0075 (10)
C24	0.0122 (11)	0.0286 (12)	0.0180 (11)	0.0029 (9)	0.0013 (9)	0.0066 (9)
C25	0.025 (2)	0.032 (2)	0.024 (2)	0.0016 (16)	0.0100 (16)	−0.0058 (16)
C26	0.021 (2)	0.012 (2)	0.025 (2)	0.0019 (17)	0.0072 (18)	0.0045 (18)
C25'	0.028 (5)	0.035 (5)	0.033 (5)	−0.004 (4)	0.004 (4)	−0.010 (4)
C26'	0.048 (8)	0.011 (5)	0.023 (5)	0.009 (4)	0.003 (5)	0.000 (4)
C27	0.0254 (13)	0.0185 (10)	0.0179 (10)	0.0041 (9)	0.0057 (9)	0.0064 (8)

Geometric parameters (Å, º) top

Ru1—Cl1	2.3924 (6)	C14—C15	1.394 (3)
Ru1—N1	2.0706 (16)	C14—H14	0.9500
Ru1—N2	2.1209 (16)	C15—C16	1.382 (3)
Ru1—C17	2.243 (2)	C15—H15	0.9500
Ru1—C18	2.220 (2)	C16—H16	0.9500
Ru1—C19	2.183 (2)	C17—C22	1.402 (3)
Ru1—C20	2.221 (2)	C17—C18	1.408 (3)
Ru1—C21	2.161 (2)	C17—C23	1.502 (3)
Ru1—C22	2.192 (2)	C18—C19	1.420 (3)
Cl3—C27	1.765 (2)	C18—H18	0.9500
Cl4—C27	1.767 (2)	C19—C20	1.417 (3)
Cl5—C27	1.760 (2)	C19—H19	0.9500
O1—C12	1.359 (2)	C20—C21	1.418 (3)
O1—H1	0.77 (2)	C20—C24	1.521 (3)
N1—C5	1.347 (2)	C21—C22	1.418 (3)
N1—C1	1.349 (3)	C21—H21	0.9500
N2—C10	1.356 (2)	C22—H22	0.9500
N2—C6	1.367 (2)	C23—H23A	0.9800
C1—C2	1.377 (3)	C23—H23B	0.9800
C1—H1A	0.9500	C23—H23C	0.9800
C2—C3	1.378 (3)	C24—C25'	1.471 (7)
C2—H2	0.9500	C24—C26'	1.479 (8)
C3—C4	1.389 (3)	C24—C26	1.529 (4)
C3—H3	0.9500	C24—C25	1.569 (4)
C4—C5	1.389 (3)	C24—H24A	0.9601
C4—H4	0.9500	C24—H24B	0.9600
C5—C6	1.467 (3)	C25—H25A	0.9800
C6—C7	1.388 (3)	C25—H25B	0.9800
C7—C8	1.379 (3)	C25—H25C	0.9800
C7—H7	0.9500	C26—H26A	0.9800
C8—C9	1.379 (3)	C26—H26B	0.9800
C8—H8	0.9500	C26—H26C	0.9800
C9—C10	1.391 (3)	C25'—H25D	0.9800
C9—H9	0.9500	C25'—H25E	0.9800
C10—C11	1.487 (3)	C25'—H25F	0.9800
C11—C16	1.396 (3)	C26'—H26D	0.9800
C11—C12	1.407 (3)	C26'—H26E	0.9800
C12—C13	1.397 (3)	C26'—H26F	0.9800
C13—C14	1.384 (3)	C27—H27	1.0000
C13—H13	0.9500

N1—Ru1—N2	77.00 (6)	C15—C16—C11	120.62 (19)
N1—Ru1—C21	88.96 (7)	C15—C16—H16	119.7
N2—Ru1—C21	135.12 (7)	C11—C16—H16	119.7
N1—Ru1—C19	134.95 (7)	C22—C17—C18	118.48 (19)
N2—Ru1—C19	93.42 (7)	C22—C17—C23	121.0 (2)
C21—Ru1—C19	67.04 (8)	C18—C17—C23	120.5 (2)
N1—Ru1—C22	105.25 (7)	C22—C17—Ru1	69.58 (11)
N2—Ru1—C22	171.71 (7)	C18—C17—Ru1	70.72 (11)
C21—Ru1—C22	38.02 (7)	C23—C17—Ru1	128.70 (16)
C19—Ru1—C22	79.32 (8)	C17—C18—C19	120.3 (2)
N1—Ru1—C18	168.10 (7)	C17—C18—Ru1	72.51 (12)
N2—Ru1—C18	110.11 (7)	C19—C18—Ru1	69.79 (11)
C21—Ru1—C18	79.28 (8)	C17—C18—H18	119.9
C19—Ru1—C18	37.61 (7)	C19—C18—H18	119.9
C22—Ru1—C18	66.35 (8)	Ru1—C18—H18	130.5
N1—Ru1—C20	101.30 (7)	C20—C19—C18	122.55 (19)
N2—Ru1—C20	103.22 (7)	C20—C19—Ru1	72.67 (11)
C21—Ru1—C20	37.73 (7)	C18—C19—Ru1	72.60 (12)
C19—Ru1—C20	37.54 (7)	C20—C19—H19	118.7
C22—Ru1—C20	68.57 (8)	C18—C19—H19	118.7
C18—Ru1—C20	68.15 (8)	Ru1—C19—H19	128.4
N1—Ru1—C17	138.90 (7)	C19—C20—C21	115.58 (18)
N2—Ru1—C17	143.16 (7)	C19—C20—C24	122.46 (18)
C21—Ru1—C17	67.55 (8)	C21—C20—C24	121.96 (18)
C19—Ru1—C17	67.27 (8)	C19—C20—Ru1	69.79 (12)
C22—Ru1—C17	36.82 (8)	C21—C20—Ru1	68.83 (11)
C18—Ru1—C17	36.77 (7)	C24—C20—Ru1	132.06 (14)
C20—Ru1—C17	80.77 (8)	C20—C21—C22	122.46 (19)
N1—Ru1—Cl1	84.07 (5)	C20—C21—Ru1	73.44 (12)
N2—Ru1—Cl1	86.47 (4)	C22—C21—Ru1	72.18 (12)
C21—Ru1—Cl1	134.78 (5)	C20—C21—H21	118.8
C19—Ru1—Cl1	139.91 (6)	C22—C21—H21	118.8
C22—Ru1—Cl1	101.66 (6)	Ru1—C21—H21	127.9
C18—Ru1—Cl1	105.53 (6)	C17—C22—C21	120.62 (19)
C20—Ru1—Cl1	169.72 (5)	C17—C22—Ru1	73.59 (12)
C17—Ru1—Cl1	89.41 (6)	C21—C22—Ru1	69.80 (11)
C12—O1—H1	114 (2)	C17—C22—H22	119.7
C5—N1—C1	119.58 (17)	C21—C22—H22	119.7
C5—N1—Ru1	117.58 (13)	Ru1—C22—H22	129.3
C1—N1—Ru1	122.77 (13)	C17—C23—H23A	109.5
C10—N2—C6	118.36 (16)	C17—C23—H23B	109.5
C10—N2—Ru1	127.07 (12)	H23A—C23—H23B	109.5
C6—N2—Ru1	114.45 (13)	C17—C23—H23C	109.5
N1—C1—C2	121.60 (19)	H23A—C23—H23C	109.5
N1—C1—H1A	119.2	H23B—C23—H23C	109.5
C2—C1—H1A	119.2	C25'—C24—C26'	119.1 (7)
C1—C2—C3	119.3 (2)	C25'—C24—C20	111.0 (4)
C1—C2—H2	120.3	C26'—C24—C20	114.9 (8)
C3—C2—H2	120.3	C25'—C24—C26	130.3 (6)
C2—C3—C4	119.4 (2)	C20—C24—C26	112.7 (3)
C2—C3—H3	120.3	C26'—C24—C25	92.8 (6)
C4—C3—H3	120.3	C20—C24—C25	112.8 (2)
C3—C4—C5	118.83 (19)	C26—C24—C25	107.2 (3)
C3—C4—H4	120.6	C25'—C24—H24A	79.2
C5—C4—H4	120.6	C26'—C24—H24A	119.5
N1—C5—C4	121.24 (18)	C20—C24—H24A	108.0
N1—C5—C6	114.50 (16)	C26—C24—H24A	108.0
C4—C5—C6	124.24 (18)	C25—C24—H24A	107.9
N2—C6—C7	122.16 (18)	C25'—C24—H24B	102.7
N2—C6—C5	115.25 (16)	C26'—C24—H24B	103.4
C7—C6—C5	122.58 (17)	C20—C24—H24B	103.2
C8—C7—C6	119.05 (18)	C26—C24—H24B	89.4
C8—C7—H7	120.5	C25—C24—H24B	129.2
C6—C7—H7	120.5	C24—C25—H25A	109.5
C9—C8—C7	118.88 (18)	C24—C25—H25B	109.5
C9—C8—H8	120.6	C24—C25—H25C	109.5
C7—C8—H8	120.6	C24—C26—H26A	109.5
C8—C9—C10	120.56 (19)	C24—C26—H26B	109.5
C8—C9—H9	119.7	C24—C26—H26C	109.5
C10—C9—H9	119.7	C24—C25'—H25D	109.5
N2—C10—C9	120.80 (17)	C24—C25'—H25E	109.5
N2—C10—C11	119.58 (16)	H25D—C25'—H25E	109.5
C9—C10—C11	119.61 (18)	C24—C25'—H25F	109.5
C16—C11—C12	119.10 (18)	H25D—C25'—H25F	109.5
C16—C11—C10	121.23 (18)	H25E—C25'—H25F	109.5
C12—C11—C10	119.64 (17)	C24—C26'—H26D	109.5
O1—C12—C13	122.38 (18)	C24—C26'—H26E	109.5
O1—C12—C11	117.55 (17)	H26D—C26'—H26E	109.5
C13—C12—C11	119.98 (18)	C24—C26'—H26F	109.5
C14—C13—C12	119.89 (19)	H26D—C26'—H26F	109.5
C14—C13—H13	120.1	H26E—C26'—H26F	109.5
C12—C13—H13	120.1	Cl5—C27—Cl3	110.73 (12)
C13—C14—C15	120.39 (18)	Cl5—C27—Cl4	110.80 (12)
C13—C14—H14	119.8	Cl3—C27—Cl4	110.02 (12)
C15—C14—H14	119.8	Cl5—C27—H27	108.4
C16—C15—C14	119.99 (18)	Cl3—C27—H27	108.4
C16—C15—H15	120.0	Cl4—C27—H27	108.4
C14—C15—H15	120.0

N2—Ru1—N1—C5	8.66 (13)	C22—Ru1—C18—C17	−29.09 (13)
C21—Ru1—N1—C5	−128.35 (15)	C20—Ru1—C18—C17	−104.36 (14)
C19—Ru1—N1—C5	−73.06 (17)	Cl1—Ru1—C18—C17	67.07 (13)
C22—Ru1—N1—C5	−163.10 (14)	N1—Ru1—C18—C19	56.9 (4)
C18—Ru1—N1—C5	−119.3 (3)	N2—Ru1—C18—C19	−68.20 (13)
C20—Ru1—N1—C5	−92.48 (15)	C21—Ru1—C18—C19	66.12 (13)
C17—Ru1—N1—C5	178.64 (13)	C22—Ru1—C18—C19	103.71 (14)
Cl1—Ru1—N1—C5	96.39 (14)	C20—Ru1—C18—C19	28.43 (12)
N2—Ru1—N1—C1	−174.45 (17)	C17—Ru1—C18—C19	132.79 (19)
C21—Ru1—N1—C1	48.54 (17)	Cl1—Ru1—C18—C19	−160.13 (11)
C19—Ru1—N1—C1	103.83 (17)	C17—C18—C19—C20	−1.1 (3)
C22—Ru1—N1—C1	13.79 (18)	Ru1—C18—C19—C20	−55.23 (17)
C18—Ru1—N1—C1	57.6 (4)	C17—C18—C19—Ru1	54.14 (17)
C20—Ru1—N1—C1	84.41 (17)	N1—Ru1—C19—C20	−32.36 (16)
C17—Ru1—N1—C1	−4.5 (2)	N2—Ru1—C19—C20	−107.36 (12)
Cl1—Ru1—N1—C1	−86.72 (16)	C21—Ru1—C19—C20	30.85 (11)
N1—Ru1—N2—C10	174.27 (16)	C22—Ru1—C19—C20	68.59 (12)
C21—Ru1—N2—C10	−110.70 (17)	C18—Ru1—C19—C20	133.50 (18)
C19—Ru1—N2—C10	−50.29 (16)	C17—Ru1—C19—C20	105.06 (13)
C18—Ru1—N2—C10	−15.70 (17)	Cl1—Ru1—C19—C20	164.07 (9)
C20—Ru1—N2—C10	−86.97 (16)	N1—Ru1—C19—C18	−165.86 (11)
C17—Ru1—N2—C10	5.3 (2)	N2—Ru1—C19—C18	119.14 (12)
Cl1—Ru1—N2—C10	89.55 (15)	C21—Ru1—C19—C18	−102.65 (13)
N1—Ru1—N2—C6	−9.87 (13)	C22—Ru1—C19—C18	−64.91 (13)
C21—Ru1—N2—C6	65.17 (16)	C20—Ru1—C19—C18	−133.50 (18)
C19—Ru1—N2—C6	125.57 (14)	C17—Ru1—C19—C18	−28.44 (12)
C18—Ru1—N2—C6	160.16 (13)	Cl1—Ru1—C19—C18	30.57 (16)
C20—Ru1—N2—C6	88.90 (14)	C18—C19—C20—C21	2.3 (3)
C17—Ru1—N2—C6	−178.87 (13)	Ru1—C19—C20—C21	−52.92 (15)
Cl1—Ru1—N2—C6	−94.59 (13)	C18—C19—C20—C24	−177.07 (19)
C5—N1—C1—C2	2.8 (3)	Ru1—C19—C20—C24	127.73 (18)
Ru1—N1—C1—C2	−174.08 (16)	C18—C19—C20—Ru1	55.20 (18)
N1—C1—C2—C3	−1.5 (3)	N1—Ru1—C20—C19	157.28 (12)
C1—C2—C3—C4	−0.8 (3)	N2—Ru1—C20—C19	78.16 (12)
C2—C3—C4—C5	1.8 (3)	C21—Ru1—C20—C19	−129.49 (17)
C1—N1—C5—C4	−1.7 (3)	C22—Ru1—C20—C19	−100.62 (13)
Ru1—N1—C5—C4	175.28 (15)	C18—Ru1—C20—C19	−28.48 (11)
C1—N1—C5—C6	176.91 (18)	C17—Ru1—C20—C19	−64.47 (12)
Ru1—N1—C5—C6	−6.1 (2)	Cl1—Ru1—C20—C19	−82.0 (3)
C3—C4—C5—N1	−0.5 (3)	N1—Ru1—C20—C21	−73.23 (12)
C3—C4—C5—C6	−179.03 (19)	N2—Ru1—C20—C21	−152.35 (11)
C10—N2—C6—C7	5.0 (3)	C19—Ru1—C20—C21	129.49 (17)
Ru1—N2—C6—C7	−171.30 (15)	C22—Ru1—C20—C21	28.87 (12)
C10—N2—C6—C5	−173.88 (16)	C18—Ru1—C20—C21	101.01 (13)
Ru1—N2—C6—C5	9.9 (2)	C17—Ru1—C20—C21	65.02 (12)
N1—C5—C6—N2	−2.7 (2)	Cl1—Ru1—C20—C21	47.5 (4)
C4—C5—C6—N2	175.84 (18)	N1—Ru1—C20—C24	41.3 (2)
N1—C5—C6—C7	178.44 (18)	N2—Ru1—C20—C24	−37.8 (2)
C4—C5—C6—C7	−3.0 (3)	C21—Ru1—C20—C24	114.5 (2)
N2—C6—C7—C8	−2.2 (3)	C19—Ru1—C20—C24	−116.0 (2)
C5—C6—C7—C8	176.54 (19)	C22—Ru1—C20—C24	143.4 (2)
C6—C7—C8—C9	−1.7 (3)	C18—Ru1—C20—C24	−144.5 (2)
C7—C8—C9—C10	2.7 (3)	C17—Ru1—C20—C24	179.5 (2)
C6—N2—C10—C9	−3.8 (3)	Cl1—Ru1—C20—C24	162.0 (2)
Ru1—N2—C10—C9	171.88 (14)	C19—C20—C21—C22	−2.0 (3)
C6—N2—C10—C11	175.17 (17)	C24—C20—C21—C22	177.34 (19)
Ru1—N2—C10—C11	−9.1 (3)	Ru1—C20—C21—C22	−55.43 (18)
C8—C9—C10—N2	0.1 (3)	C19—C20—C21—Ru1	53.41 (16)
C8—C9—C10—C11	−178.93 (19)	C24—C20—C21—Ru1	−127.24 (18)
N2—C10—C11—C16	−68.5 (3)	N1—Ru1—C21—C20	110.11 (12)
C9—C10—C11—C16	110.6 (2)	N2—Ru1—C21—C20	39.81 (15)
N2—C10—C11—C12	113.5 (2)	C19—Ru1—C21—C20	−30.71 (11)
C9—C10—C11—C12	−67.5 (3)	C22—Ru1—C21—C20	−133.13 (18)
C16—C11—C12—O1	178.79 (18)	C18—Ru1—C21—C20	−68.01 (12)
C10—C11—C12—O1	−3.2 (3)	C17—Ru1—C21—C20	−104.51 (13)
C16—C11—C12—C13	2.2 (3)	Cl1—Ru1—C21—C20	−169.31 (9)
C10—C11—C12—C13	−179.74 (19)	N1—Ru1—C21—C22	−116.76 (13)
O1—C12—C13—C14	−177.60 (18)	N2—Ru1—C21—C22	172.94 (11)
C11—C12—C13—C14	−1.2 (3)	C19—Ru1—C21—C22	102.43 (14)
C12—C13—C14—C15	−0.3 (3)	C18—Ru1—C21—C22	65.12 (13)
C13—C14—C15—C16	0.8 (3)	C20—Ru1—C21—C22	133.13 (18)
C14—C15—C16—C11	0.2 (3)	C17—Ru1—C21—C22	28.62 (12)
C12—C11—C16—C15	−1.7 (3)	Cl1—Ru1—C21—C22	−36.18 (15)
C10—C11—C16—C15	−179.75 (19)	C18—C17—C22—C21	0.7 (3)
N1—Ru1—C17—C22	30.28 (18)	C23—C17—C22—C21	177.4 (2)
N2—Ru1—C17—C22	−166.14 (12)	Ru1—C17—C22—C21	53.67 (17)
C21—Ru1—C17—C22	−29.49 (12)	C18—C17—C22—Ru1	−52.93 (17)
C19—Ru1—C17—C22	−102.96 (14)	C23—C17—C22—Ru1	123.7 (2)
C18—Ru1—C17—C22	−132.01 (19)	C20—C21—C22—C17	0.6 (3)
C20—Ru1—C17—C22	−66.37 (13)	Ru1—C21—C22—C17	−55.43 (18)
Cl1—Ru1—C17—C22	110.55 (12)	C20—C21—C22—Ru1	56.00 (17)
N1—Ru1—C17—C18	162.29 (12)	N1—Ru1—C22—C17	−159.91 (12)
N2—Ru1—C17—C18	−34.14 (18)	C21—Ru1—C22—C17	132.38 (19)
C21—Ru1—C17—C18	102.51 (14)	C19—Ru1—C22—C17	66.16 (13)
C19—Ru1—C17—C18	29.05 (12)	C18—Ru1—C22—C17	29.05 (12)
C22—Ru1—C17—C18	132.01 (19)	C20—Ru1—C22—C17	103.71 (14)
C20—Ru1—C17—C18	65.63 (13)	Cl1—Ru1—C22—C17	−72.95 (13)
Cl1—Ru1—C17—C18	−117.45 (12)	N1—Ru1—C22—C21	67.72 (13)
N1—Ru1—C17—C23	−83.6 (2)	C19—Ru1—C22—C21	−66.21 (13)
N2—Ru1—C17—C23	79.9 (2)	C18—Ru1—C22—C21	−103.32 (14)
C21—Ru1—C17—C23	−143.4 (2)	C20—Ru1—C22—C21	−28.67 (12)
C19—Ru1—C17—C23	143.1 (2)	C17—Ru1—C22—C21	−132.38 (19)
C22—Ru1—C17—C23	−113.9 (3)	Cl1—Ru1—C22—C21	154.67 (11)
C18—Ru1—C17—C23	114.1 (3)	C19—C20—C24—C25'	8.1 (9)
C20—Ru1—C17—C23	179.7 (2)	C21—C20—C24—C25'	−171.2 (9)
Cl1—Ru1—C17—C23	−3.4 (2)	Ru1—C20—C24—C25'	99.4 (9)
C22—C17—C18—C19	−0.5 (3)	C19—C20—C24—C26'	−130.7 (8)
C23—C17—C18—C19	−177.12 (19)	C21—C20—C24—C26'	50.0 (8)
Ru1—C17—C18—C19	−52.88 (17)	Ru1—C20—C24—C26'	−39.4 (8)
C22—C17—C18—Ru1	52.40 (17)	C19—C20—C24—C26	−147.6 (3)
C23—C17—C18—Ru1	−124.2 (2)	C21—C20—C24—C26	33.1 (4)
N1—Ru1—C18—C17	−75.9 (3)	Ru1—C20—C24—C26	−56.3 (4)
N2—Ru1—C18—C17	159.00 (12)	C19—C20—C24—C25	−26.0 (4)
C21—Ru1—C18—C17	−66.68 (13)	C21—C20—C24—C25	154.7 (3)
C19—Ru1—C18—C17	−132.79 (19)	Ru1—C20—C24—C25	65.3 (4)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1···Cl2ⁱ	0.77 (2)	2.22 (2)	2.9782 (17)	169 (3)

Symmetry code: (i) x−1, y, z.

Experimental details

Crystal data
Chemical formula	[RuCl(C₁₀H₁₄)(C₁₆H₁₂N₂O)]Cl·CHCl₃
M_r	673.83
Crystal system, space group	Triclinic, P1
Temperature (K)	113
a, b, c (Å)	9.2135 (14), 12.8915 (19), 13.527 (2)
α, β, γ (°)	105.406 (3), 109.022 (2), 102.663 (3)
V (Å³)	1379.4 (4)
Z	2
Radiation type	Mo Kα
µ (mm⁻¹)	1.08
Crystal size (mm)	0.34 × 0.32 × 0.26

Data collection
Diffractometer	Rigaku Saturn
Absorption correction	Multi-scan (Jacobson, 1998)
T_min, T_max	0.711, 0.767
No. of measured, independent and observed [I > 2σ(I)] reflections	12987, 6455, 5056
R_int	0.032
(sin θ/λ)_max (Å⁻¹)	0.658

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.026, 0.064, 0.99
No. of reflections	6455
No. of parameters	354
No. of restraints	48
H-atom treatment	H atoms treated by a mixture of independent and constrained refinement
Δρ_max, Δρ_min (e Å⁻³)	0.50, −0.53

Computer programs: CrystalClear (Rigaku, 2000), CrystalClear, SHELXS97 (Sheldrick, 1997), SHELXL97 (Sheldrick, 1997), SHELXTL (Bruker, 1998), CrystalStructure (Rigaku/MSC, 2005).

Selected geometric parameters (Å, º) top

Ru1—Cl1	2.3924 (6)	Ru1—C19	2.183 (2)
Ru1—N1	2.0706 (16)	Ru1—C20	2.221 (2)
Ru1—N2	2.1209 (16)	Ru1—C21	2.161 (2)
Ru1—C17	2.243 (2)	Ru1—C22	2.192 (2)
Ru1—C18	2.220 (2)

N1—Ru1—N2	77.00 (6)	N2—Ru1—Cl1	86.47 (4)
N1—Ru1—Cl1	84.07 (5)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1···Cl2ⁱ	0.77 (2)	2.22 (2)	2.9782 (17)	169 (3)

Symmetry code: (i) x−1, y, z.

Subscribe to Acta Crystallographica Section E: Crystallographic Communications

Buy online

You may purchase this article in PDF and/or HTML formats. For purchasers in the European Community who do not have a VAT number, VAT will be added at the local rate. Payments to the IUCr are handled by WorldPay, who will accept payment by credit card in several currencies. To purchase the article, please complete the form below (fields marked * are required), and then click on `Continue'.

E-mail address*
Repeat e-mail address* (for error checking)

Format*	PDF (US $40)
	HTML (US $40)
	PDF+HTML (US $50)
In order for VAT to be shown for your country javascript needs to be enabled.

VAT number (non-UK EC countries only)
Country*

Terms and conditions of use
Contact us

Format		BIBTeX
		EndNote
		RefMan
		Refer
		Medline
		CIF
		SGML
		Text
		Plain Text

Format		BIBTeX
		EndNote
		RefMan
		Refer
		Medline
		CIF
		SGML
		Text
		Plain Text

Search IUCr Journals		doi		Advanced search
Author		volume	page