Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536807023975/xu2245sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S1600536807023975/xu2245Isup2.hkl |
CCDC reference: 621429
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
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.
Hydroxy H atom was located in a difference Fourier map and refined freely. Other H atoms were positioned geometrically and refined using a riding model, with C—H = 0.95 – 1.00 Å and Uiso(H) = 1.5Ueq(C) for methyl and 1.2Ueq(C) for others. The C25 and C26 atoms of isopropyl group were disordered over two positions. The C—C distances of disordered isopropyl group were restrained at 1.54 (1) Å, occupancies were refined to 0.701 (13) and 0.299 (13), respectively.
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.
For related structures, see: Bardwell et al. (1996); Poyatos et al. (2004). For synthesis, see: Jeffery et al. (1992).
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).
[RuCl(C10H14)(C16H12N2O)]Cl·CHCl3 | Z = 2 |
Mr = 673.83 | F(000) = 680 |
Triclinic, P1 | Dx = 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 |
Rigaku Saturn diffractometer | 6455 independent reflections |
Radiation source: rotating anode | 5056 reflections with I > 2σ(I) |
Confocal monochromator | Rint = 0.032 |
Detector resolution: 7.31 pixels mm-1 | θmax = 27.9°, θmin = 1.7° |
ω scans | h = −11→12 |
Absorption correction: multi-scan (Jacobson, 1998) | k = −16→13 |
Tmin = 0.711, Tmax = 0.767 | l = −17→17 |
12987 measured reflections |
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(Fo2) + (0.0278P)2] where P = (Fo2 + 2Fc2)/3 |
S = 0.99 | (Δ/σ)max = 0.003 |
6455 reflections | Δρmax = 0.50 e Å−3 |
354 parameters | Δρmin = −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) |
[RuCl(C10H14)(C16H12N2O)]Cl·CHCl3 | γ = 102.663 (3)° |
Mr = 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)° |
Rigaku Saturn diffractometer | 6455 independent reflections |
Absorption correction: multi-scan (Jacobson, 1998) | 5056 reflections with I > 2σ(I) |
Tmin = 0.711, Tmax = 0.767 | Rint = 0.032 |
12987 measured reflections |
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 | Δρmax = 0.50 e Å−3 |
6455 reflections | Δρmin = −0.53 e Å−3 |
354 parameters |
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 | 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* |
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) |
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) |
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 |
Mr | 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) |
Tmin, Tmax | 0.711, 0.767 |
No. of measured, independent and observed [I > 2σ(I)] reflections | 12987, 6455, 5056 |
Rint | 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 |
Δρmax, Δρmin (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).
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) |
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. |
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.