

Supporting information
![]() | Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536810047033/jh2228sup1.cif |
![]() | Structure factor file (CIF format) https://doi.org/10.1107/S1600536810047033/jh2228Isup2.hkl |
CCDC reference: 797152
Key indicators
- Single-crystal X-ray study
- T = 291 K
- Mean
(C-C) = 0.008 Å
- R factor = 0.049
- wR factor = 0.117
- Data-to-parameter ratio = 16.1
checkCIF/PLATON results
No syntax errors found
Alert level C PLAT910_ALERT_3_C Missing # of FCF Reflections Below Th(Min) ..... 1
Alert level G REFLT03_ALERT_4_G Please check that the estimate of the number of Friedel pairs is correct. If it is not, please give the correct count in the _publ_section_exptl_refinement section of the submitted CIF. From the CIF: _diffrn_reflns_theta_max 26.00 From the CIF: _reflns_number_total 6304 Count of symmetry unique reflns 3582 Completeness (_total/calc) 175.99% TEST3: Check Friedels for noncentro structure Estimate of Friedel pairs measured 2722 Fraction of Friedel pairs measured 0.760 Are heavy atom types Z>Si present yes PLAT917_ALERT_2_G The FCF is likely NOT based on a BASF/TWIN Flack !
0 ALERT level A = In general: serious problem 0 ALERT level B = Potentially serious problem 1 ALERT level C = Check and explain 2 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 1 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
The synthesis of the title compound 1 was carried out as follows. 2-methyl-8-(pyridineyl-2-methoxy)-quinoline (0.286 g, 0.55 mmol) was added to a solution of RuCl2(PPh3)3 (0.491 g, 0.50 mmol) in CH3OH (25 ml). This mixture was refluxed for 8 h and then evaporated to dryness. The orange solid residue was dissolved in CH2Cl2 (ca 3 ml) and the resulting solution was transferred to a silica gel chromatography column. Elution with CH2Cl2/CH3OH (40:1) gave a yellow-orange band, from which complex 1 was obtained after solvent removal. Crystal of 1 suitable for X-ary structure determination was grown from CH3OH solution of the complex layered with ethyl ether.
H atoms on C atoms were placed in idealized positions (C—H = 0.93—0.97 Å) and refined as riding atoms, with the Uiso(H) = 1.2 or 1.5Ueq(C). H atom attached to O atom are located in a difference Fourier map and refined as riding in their 'as found' positions with the Uiso(H) = 1.5Ueq(O).
The N,O,N'-tridentate ligands with two pyridine-like donors and an ether donor are potentially a doubly chelating ligands in coordination chemistry. The presence of the flexible methylene and ether linkages allows the ligands to act as a folded N,N'-bidentate ligands or N,O,N'-tridentate ligands in meridional or facial arrangement, coordination to the metal coordinate (Al-Mandhary & Steel, 2003; Xu et al. 2009). Here, we report the synthesis and crystal structure of the title complex 1, [Ru(C16H14N2O)(PPh3)Cl2.CH3OH, which combines 2-methyl-8-(pyridineyl-2-methoxy)-quinoline and triphenylphosphane ligands. The molecular structure of the title compound is shown in Fig. 1. In the title complex 1, the ruthenium atom center is in a pseudooctahedral environment with the two nitrogen atoms and one oxygen atom which from 2-methyl-8-(pyridineyl-2-methoxy)-quinoline acts as a mer N,O,N'-tridentate ligand, two cis chlorine atoms and one phosphorus atom from PPh3 ligand trans to one chloride. The N—Ru—N angle is 158.25 (17)°. The N1—Ru—O1 and N2—Ru—O1 angles are 79.47 (17)° and 79.66 (16)°, respectively. The coordination between N,O,N'-tridentate ligand and the RuII yields two five-membered rings, RuN1C6C5O1 and RuO1C7C12N2. The Ru—Cl1 distance [2.4905 (14) Å], which is trans to the PPh3 ligand, is longer than the Ru—Cl2 distance [2.4104 (14) Å], similar differences are in agreement with reported value (Deng et al. 2005; Xu et al. 2009). The Ru—N(pyridine) [2.067 (5) Å], Ru—N(quinoline) [2.163 (5) Å], Ru—O [2.060 (3) Å] and Ru—P [2.2931 (15) Å] are similar to reported value (Deng et al. 2005; Xu et al. 2009).
For related structures, see: Al-Mandhary & Steel (2003); Deng et al. (2005); Xu et al. (2009).
Data collection: SMART (Bruker, 2003); cell refinement: SAINT-Plus (Bruker, 2003); data reduction: SAINT-Plus (Bruker, 2003); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXTL (Sheldrick, 2008).
![]() | Fig. 1. The structure of 1, with atom lables and 30% probability displacement ellipsoids. |
[RuCl2(C16H14N2O)(C18H15P)]·CH4O | F(000) = 1464 |
Mr = 716.57 | Dx = 1.478 Mg m−3 |
Orthorhombic, P212121 | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: P 2ac 2ab | Cell parameters from 592 reflections |
a = 8.868 (2) Å | θ = 2.4–13.2° |
b = 11.480 (2) Å | µ = 0.74 mm−1 |
c = 31.6351 (18) Å | T = 291 K |
V = 3220.7 (10) Å3 | Block, orange |
Z = 4 | 0.28 × 0.24 × 0.22 mm |
Bruker SMART APEX CCD diffractometer | 6304 independent reflections |
Radiation source: sealed tube | 5620 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.030 |
phi and ω scans | θmax = 26.0°, θmin = 1.9° |
Absorption correction: multi-scan (SADABS; Sheldrick, 2003) | h = −10→9 |
Tmin = 0.820, Tmax = 0.855 | k = −14→10 |
17669 measured reflections | l = −38→38 |
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)] = 0.049 | H-atom parameters constrained |
wR(F2) = 0.117 | w = 1/[σ2(Fo2) + (0.06P)2 + 1.99P] where P = (Fo2 + 2Fc2)/3 |
S = 1.10 | (Δ/σ)max < 0.001 |
6304 reflections | Δρmax = 0.70 e Å−3 |
391 parameters | Δρmin = −0.91 e Å−3 |
0 restraints | Absolute structure: Flack (1983), 2722 Friedel pairs |
Primary atom site location: structure-invariant direct methods | Absolute structure parameter: 0.06 (4) |
[RuCl2(C16H14N2O)(C18H15P)]·CH4O | V = 3220.7 (10) Å3 |
Mr = 716.57 | Z = 4 |
Orthorhombic, P212121 | Mo Kα radiation |
a = 8.868 (2) Å | µ = 0.74 mm−1 |
b = 11.480 (2) Å | T = 291 K |
c = 31.6351 (18) Å | 0.28 × 0.24 × 0.22 mm |
Bruker SMART APEX CCD diffractometer | 6304 independent reflections |
Absorption correction: multi-scan (SADABS; Sheldrick, 2003) | 5620 reflections with I > 2σ(I) |
Tmin = 0.820, Tmax = 0.855 | Rint = 0.030 |
17669 measured reflections |
R[F2 > 2σ(F2)] = 0.049 | H-atom parameters constrained |
wR(F2) = 0.117 | Δρmax = 0.70 e Å−3 |
S = 1.10 | Δρmin = −0.91 e Å−3 |
6304 reflections | Absolute structure: Flack (1983), 2722 Friedel pairs |
391 parameters | Absolute structure parameter: 0.06 (4) |
0 restraints |
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 | ||
C1 | 0.1967 (7) | 0.4572 (6) | 0.6458 (2) | 0.0547 (15) | |
H1 | 0.1733 | 0.4993 | 0.6216 | 0.066* | |
C2 | 0.0977 (8) | 0.3754 (6) | 0.6601 (2) | 0.0547 (16) | |
H2 | 0.0091 | 0.3628 | 0.6451 | 0.066* | |
C3 | 0.1231 (7) | 0.3129 (5) | 0.69486 (18) | 0.0481 (14) | |
H3 | 0.0548 | 0.2561 | 0.7033 | 0.058* | |
C4 | 0.2514 (7) | 0.3333 (5) | 0.71807 (18) | 0.0482 (14) | |
H4 | 0.2707 | 0.2934 | 0.7431 | 0.058* | |
C5 | 0.3511 (6) | 0.4166 (5) | 0.70246 (16) | 0.0396 (11) | |
C6 | 0.4939 (7) | 0.4460 (5) | 0.72707 (17) | 0.0455 (12) | |
H6A | 0.4734 | 0.5064 | 0.7477 | 0.055* | |
H6B | 0.5309 | 0.3776 | 0.7418 | 0.055* | |
C7 | 0.7414 (7) | 0.5321 (5) | 0.71092 (17) | 0.0406 (12) | |
C8 | 0.8219 (7) | 0.4838 (5) | 0.74429 (15) | 0.0424 (13) | |
H8 | 0.7791 | 0.4250 | 0.7606 | 0.051* | |
C9 | 0.9665 (7) | 0.5233 (5) | 0.75332 (18) | 0.0512 (17) | |
H9 | 1.0204 | 0.4910 | 0.7757 | 0.061* | |
C10 | 1.0306 (6) | 0.6112 (5) | 0.72899 (18) | 0.0499 (15) | |
H10 | 1.1273 | 0.6376 | 0.7350 | 0.060* | |
C11 | 0.9500 (6) | 0.6594 (5) | 0.69561 (19) | 0.0416 (13) | |
C12 | 0.8054 (6) | 0.6199 (5) | 0.68658 (18) | 0.0409 (12) | |
C13 | 0.7889 (7) | 0.7560 (5) | 0.6289 (2) | 0.0498 (15) | |
C14 | 0.9335 (6) | 0.7956 (5) | 0.63790 (18) | 0.0481 (14) | |
H14 | 0.9764 | 0.8543 | 0.6216 | 0.058* | |
C15 | 1.0141 (8) | 0.7473 (4) | 0.67127 (15) | 0.0461 (13) | |
H15 | 1.1108 | 0.7737 | 0.6773 | 0.055* | |
C16 | 0.6974 (8) | 0.8152 (6) | 0.59660 (19) | 0.0556 (16) | |
H16A | 0.6168 | 0.7648 | 0.5878 | 0.083* | |
H16B | 0.7595 | 0.8337 | 0.5727 | 0.083* | |
H16C | 0.6561 | 0.8855 | 0.6082 | 0.083* | |
C17 | 0.4278 (6) | 0.3833 (5) | 0.56457 (16) | 0.0389 (12) | |
C18 | 0.3214 (7) | 0.4467 (5) | 0.54310 (19) | 0.0492 (15) | |
H18 | 0.3255 | 0.5276 | 0.5434 | 0.059* | |
C19 | 0.2062 (7) | 0.3896 (6) | 0.52066 (19) | 0.0520 (16) | |
H19 | 0.1352 | 0.4319 | 0.5054 | 0.062* | |
C20 | 0.2012 (7) | 0.2744 (5) | 0.5218 (2) | 0.0510 (15) | |
H20 | 0.1250 | 0.2367 | 0.5069 | 0.061* | |
C21 | 0.3002 (7) | 0.2094 (6) | 0.54320 (19) | 0.0514 (15) | |
H21 | 0.2917 | 0.1287 | 0.5429 | 0.062* | |
C22 | 0.4163 (8) | 0.2625 (5) | 0.5660 (2) | 0.0526 (15) | |
H22 | 0.4840 | 0.2183 | 0.5818 | 0.063* | |
C23 | 0.6972 (6) | 0.3305 (5) | 0.61146 (17) | 0.0397 (12) | |
C24 | 0.6582 (7) | 0.2702 (5) | 0.64730 (19) | 0.0469 (13) | |
H24 | 0.5781 | 0.2966 | 0.6637 | 0.056* | |
C25 | 0.7358 (8) | 0.1700 (5) | 0.65976 (17) | 0.0490 (15) | |
H25 | 0.7136 | 0.1346 | 0.6855 | 0.059* | |
C26 | 0.8444 (8) | 0.1244 (5) | 0.63414 (19) | 0.0529 (16) | |
H26 | 0.8935 | 0.0559 | 0.6416 | 0.063* | |
C27 | 0.8805 (6) | 0.1802 (4) | 0.59724 (17) | 0.0401 (12) | |
H27 | 0.9554 | 0.1497 | 0.5799 | 0.048* | |
C28 | 0.8063 (7) | 0.2826 (5) | 0.58537 (16) | 0.0407 (12) | |
H28 | 0.8302 | 0.3186 | 0.5599 | 0.049* | |
C29 | 0.6986 (7) | 0.5251 (5) | 0.55537 (18) | 0.0456 (14) | |
C30 | 0.6518 (7) | 0.5601 (5) | 0.51666 (17) | 0.0462 (14) | |
H30 | 0.5546 | 0.5422 | 0.5077 | 0.055* | |
C31 | 0.7457 (7) | 0.6215 (5) | 0.4905 (2) | 0.0510 (16) | |
H31 | 0.7118 | 0.6441 | 0.4639 | 0.061* | |
C32 | 0.8927 (7) | 0.6507 (5) | 0.50324 (19) | 0.0485 (15) | |
H32 | 0.9544 | 0.6944 | 0.4855 | 0.058* | |
C33 | 0.9447 (7) | 0.6144 (5) | 0.54189 (19) | 0.0499 (15) | |
H33 | 1.0441 | 0.6272 | 0.5500 | 0.060* | |
C34 | 0.8443 (7) | 0.5582 (5) | 0.56832 (18) | 0.0446 (14) | |
H34 | 0.8742 | 0.5415 | 0.5958 | 0.054* | |
C35 | 0.3573 (7) | 1.0239 (6) | 0.6490 (2) | 0.0559 (16) | |
H35A | 0.3218 | 1.1028 | 0.6508 | 0.084* | |
H35B | 0.4463 | 1.0214 | 0.6317 | 0.084* | |
H35C | 0.3806 | 0.9956 | 0.6768 | 0.084* | |
Cl1 | 0.43030 (16) | 0.71863 (12) | 0.70588 (4) | 0.0412 (3) | |
Cl2 | 0.35481 (17) | 0.69468 (12) | 0.60054 (5) | 0.0474 (3) | |
N1 | 0.3286 (5) | 0.4787 (4) | 0.66606 (13) | 0.0385 (10) | |
N2 | 0.7249 (5) | 0.6682 (4) | 0.65321 (14) | 0.0433 (11) | |
O1 | 0.6057 (4) | 0.4866 (3) | 0.69627 (11) | 0.0388 (8) | |
O2 | 0.2468 (5) | 0.9549 (4) | 0.63110 (15) | 0.0588 (12) | |
H2A | 0.2852 | 0.8955 | 0.6216 | 0.071* | |
P1 | 0.57943 (18) | 0.45692 (12) | 0.59589 (4) | 0.0401 (3) | |
Ru1 | 0.50826 (5) | 0.58272 (3) | 0.648543 (12) | 0.03625 (11) |
U11 | U22 | U33 | U12 | U13 | U23 | |
C1 | 0.050 (3) | 0.057 (4) | 0.057 (4) | −0.008 (3) | −0.002 (3) | −0.018 (3) |
C2 | 0.056 (4) | 0.058 (4) | 0.051 (4) | −0.014 (3) | −0.004 (3) | 0.008 (3) |
C3 | 0.054 (4) | 0.044 (3) | 0.047 (3) | −0.016 (3) | −0.014 (3) | 0.011 (3) |
C4 | 0.051 (3) | 0.050 (3) | 0.043 (3) | −0.005 (3) | −0.011 (3) | 0.008 (3) |
C5 | 0.041 (3) | 0.035 (3) | 0.044 (3) | 0.004 (3) | 0.004 (2) | 0.001 (2) |
C6 | 0.039 (3) | 0.049 (3) | 0.049 (3) | 0.012 (3) | −0.001 (3) | 0.018 (2) |
C7 | 0.042 (3) | 0.036 (3) | 0.044 (3) | −0.002 (2) | −0.012 (2) | −0.004 (2) |
C8 | 0.049 (3) | 0.051 (3) | 0.027 (3) | −0.012 (3) | −0.006 (2) | 0.006 (2) |
C9 | 0.057 (5) | 0.058 (4) | 0.038 (3) | 0.015 (3) | −0.019 (3) | −0.021 (3) |
C10 | 0.038 (3) | 0.059 (4) | 0.052 (3) | 0.005 (3) | −0.015 (3) | −0.016 (3) |
C11 | 0.030 (3) | 0.043 (3) | 0.051 (3) | −0.006 (2) | 0.001 (2) | −0.009 (2) |
C12 | 0.037 (3) | 0.034 (3) | 0.052 (3) | 0.000 (2) | −0.006 (2) | −0.012 (2) |
C13 | 0.057 (4) | 0.036 (3) | 0.056 (3) | −0.002 (3) | 0.002 (3) | −0.001 (3) |
C14 | 0.033 (3) | 0.056 (3) | 0.055 (3) | −0.005 (3) | 0.011 (3) | −0.012 (3) |
C15 | 0.053 (3) | 0.044 (3) | 0.041 (3) | 0.004 (3) | 0.019 (3) | −0.015 (2) |
C16 | 0.069 (4) | 0.051 (4) | 0.047 (3) | −0.009 (3) | 0.009 (3) | 0.011 (3) |
C17 | 0.043 (3) | 0.040 (3) | 0.034 (3) | 0.005 (2) | 0.004 (2) | −0.021 (2) |
C18 | 0.051 (3) | 0.039 (3) | 0.058 (4) | −0.001 (3) | −0.018 (3) | −0.019 (3) |
C19 | 0.043 (3) | 0.059 (4) | 0.054 (4) | 0.015 (3) | −0.011 (3) | −0.019 (3) |
C20 | 0.045 (3) | 0.044 (3) | 0.063 (4) | −0.003 (3) | −0.013 (3) | −0.022 (3) |
C21 | 0.043 (3) | 0.057 (4) | 0.054 (3) | −0.011 (3) | −0.011 (3) | −0.014 (3) |
C22 | 0.056 (4) | 0.037 (3) | 0.065 (4) | −0.015 (3) | −0.009 (3) | 0.005 (3) |
C23 | 0.037 (3) | 0.035 (3) | 0.047 (3) | −0.008 (2) | −0.009 (2) | −0.008 (2) |
C24 | 0.057 (3) | 0.039 (3) | 0.044 (3) | 0.001 (2) | −0.021 (3) | 0.000 (3) |
C25 | 0.067 (4) | 0.045 (3) | 0.035 (3) | 0.005 (3) | 0.001 (3) | 0.024 (2) |
C26 | 0.069 (4) | 0.037 (3) | 0.053 (3) | 0.022 (3) | −0.009 (3) | 0.003 (3) |
C27 | 0.041 (3) | 0.031 (3) | 0.048 (3) | 0.013 (2) | −0.012 (2) | −0.016 (2) |
C28 | 0.051 (3) | 0.046 (3) | 0.025 (2) | 0.000 (3) | −0.012 (2) | −0.004 (2) |
C29 | 0.053 (3) | 0.040 (3) | 0.044 (3) | 0.015 (3) | 0.009 (3) | 0.013 (3) |
C30 | 0.055 (4) | 0.045 (3) | 0.039 (3) | 0.004 (3) | 0.001 (3) | 0.003 (2) |
C31 | 0.049 (3) | 0.046 (3) | 0.058 (4) | 0.025 (3) | 0.019 (3) | 0.017 (3) |
C32 | 0.048 (4) | 0.047 (3) | 0.051 (3) | 0.016 (3) | 0.013 (3) | 0.026 (3) |
C33 | 0.056 (4) | 0.041 (3) | 0.054 (3) | 0.015 (2) | 0.014 (3) | 0.006 (3) |
C34 | 0.055 (3) | 0.034 (3) | 0.044 (3) | 0.007 (2) | 0.020 (3) | 0.006 (2) |
C35 | 0.064 (4) | 0.057 (4) | 0.046 (3) | −0.013 (3) | 0.023 (3) | −0.020 (3) |
Cl1 | 0.0449 (7) | 0.0410 (7) | 0.0376 (6) | −0.0005 (6) | −0.0036 (6) | −0.0007 (5) |
Cl2 | 0.0492 (8) | 0.0461 (8) | 0.0470 (7) | −0.0014 (6) | −0.0080 (6) | 0.0143 (6) |
N1 | 0.047 (3) | 0.043 (3) | 0.0254 (19) | −0.003 (2) | −0.0019 (19) | −0.0066 (18) |
N2 | 0.047 (3) | 0.048 (3) | 0.035 (2) | −0.006 (2) | −0.007 (2) | −0.006 (2) |
O1 | 0.045 (2) | 0.0283 (18) | 0.043 (2) | −0.0104 (15) | −0.0085 (17) | 0.0118 (16) |
O2 | 0.059 (3) | 0.048 (3) | 0.069 (3) | 0.022 (2) | −0.015 (2) | −0.021 (2) |
P1 | 0.0446 (8) | 0.0387 (7) | 0.0369 (7) | 0.0004 (6) | −0.0016 (6) | −0.0002 (6) |
Ru1 | 0.0366 (2) | 0.03698 (19) | 0.03518 (19) | −0.0014 (2) | −0.0037 (2) | 0.00081 (16) |
C1—N1 | 1.356 (8) | C19—H19 | 0.9300 |
C1—C2 | 1.362 (9) | C20—C21 | 1.337 (9) |
C1—H1 | 0.9300 | C20—H20 | 0.9300 |
C2—C3 | 1.332 (8) | C21—C22 | 1.398 (8) |
C2—H2 | 0.9300 | C21—H21 | 0.9300 |
C3—C4 | 1.374 (8) | C22—H22 | 0.9300 |
C3—H3 | 0.9300 | C23—C24 | 1.373 (8) |
C4—C5 | 1.393 (8) | C23—C28 | 1.385 (8) |
C4—H4 | 0.9300 | C23—P1 | 1.855 (6) |
C5—N1 | 1.369 (7) | C24—C25 | 1.397 (8) |
C5—C6 | 1.524 (8) | C24—H24 | 0.9300 |
C6—O1 | 1.466 (7) | C25—C26 | 1.363 (9) |
C6—H6A | 0.9700 | C25—H25 | 0.9300 |
C6—H6B | 0.9700 | C26—C27 | 1.370 (8) |
C7—C8 | 1.390 (8) | C26—H26 | 0.9300 |
C7—C12 | 1.390 (8) | C27—C28 | 1.398 (7) |
C7—O1 | 1.391 (7) | C27—H27 | 0.9300 |
C8—C9 | 1.390 (9) | C28—H28 | 0.9300 |
C8—H8 | 0.9300 | C29—C30 | 1.354 (8) |
C9—C10 | 1.390 (9) | C29—C34 | 1.407 (9) |
C9—H9 | 0.9300 | C29—P1 | 1.837 (6) |
C10—C11 | 1.390 (8) | C30—C31 | 1.369 (8) |
C10—H10 | 0.9300 | C30—H30 | 0.9300 |
C11—C12 | 1.390 (8) | C31—C32 | 1.404 (9) |
C11—C15 | 1.390 (8) | C31—H31 | 0.9300 |
C12—N2 | 1.390 (7) | C32—C33 | 1.372 (8) |
C13—N2 | 1.390 (8) | C32—H32 | 0.9300 |
C13—C14 | 1.390 (9) | C33—C34 | 1.382 (8) |
C13—C16 | 1.470 (9) | C33—H33 | 0.9300 |
C14—C15 | 1.390 (9) | C34—H34 | 0.9300 |
C14—H14 | 0.9300 | C35—O2 | 1.381 (7) |
C15—H15 | 0.9300 | C35—H35A | 0.9600 |
C16—H16A | 0.9600 | C35—H35B | 0.9600 |
C16—H16B | 0.9600 | C35—H35C | 0.9600 |
C16—H16C | 0.9600 | Cl1—Ru1 | 2.4905 (14) |
C17—C18 | 1.371 (8) | Cl2—Ru1 | 2.4104 (14) |
C17—C22 | 1.392 (8) | N1—Ru1 | 2.067 (5) |
C17—P1 | 1.872 (6) | N2—Ru1 | 2.162 (5) |
C18—C19 | 1.406 (8) | O1—Ru1 | 2.060 (3) |
C18—H18 | 0.9300 | O2—H2A | 0.8200 |
C19—C20 | 1.325 (9) | P1—Ru1 | 2.2931 (15) |
N1—C1—C2 | 121.7 (7) | C24—C23—P1 | 118.2 (4) |
N1—C1—H1 | 119.2 | C28—C23—P1 | 123.1 (4) |
C2—C1—H1 | 119.2 | C23—C24—C25 | 121.6 (6) |
C3—C2—C1 | 122.4 (7) | C23—C24—H24 | 119.2 |
C3—C2—H2 | 118.8 | C25—C24—H24 | 119.2 |
C1—C2—H2 | 118.8 | C26—C25—C24 | 119.8 (5) |
C2—C3—C4 | 119.3 (6) | C26—C25—H25 | 120.1 |
C2—C3—H3 | 120.4 | C24—C25—H25 | 120.1 |
C4—C3—H3 | 120.4 | C25—C26—C27 | 119.5 (5) |
C3—C4—C5 | 117.0 (5) | C25—C26—H26 | 120.2 |
C3—C4—H4 | 121.5 | C27—C26—H26 | 120.2 |
C5—C4—H4 | 121.5 | C26—C27—C28 | 120.8 (5) |
N1—C5—C4 | 124.3 (5) | C26—C27—H27 | 119.6 |
N1—C5—C6 | 115.8 (5) | C28—C27—H27 | 119.6 |
C4—C5—C6 | 119.9 (5) | C23—C28—C27 | 120.2 (5) |
O1—C6—C5 | 107.0 (4) | C23—C28—H28 | 119.9 |
O1—C6—H6A | 110.3 | C27—C28—H28 | 119.9 |
C5—C6—H6A | 110.3 | C30—C29—C34 | 117.7 (6) |
O1—C6—H6B | 110.3 | C30—C29—P1 | 125.5 (5) |
C5—C6—H6B | 110.3 | C34—C29—P1 | 116.1 (4) |
H6A—C6—H6B | 108.6 | C29—C30—C31 | 120.8 (6) |
C8—C7—C12 | 120.0 (5) | C29—C30—H30 | 119.6 |
C8—C7—O1 | 123.2 (5) | C31—C30—H30 | 119.6 |
C12—C7—O1 | 116.2 (5) | C30—C31—C32 | 120.9 (6) |
C9—C8—C7 | 120.0 (5) | C30—C31—H31 | 119.5 |
C9—C8—H8 | 120.0 | C32—C31—H31 | 119.5 |
C7—C8—H8 | 120.0 | C33—C32—C31 | 119.7 (6) |
C8—C9—C10 | 120.0 (5) | C33—C32—H32 | 120.1 |
C8—C9—H9 | 120.0 | C31—C32—H32 | 120.1 |
C10—C9—H9 | 120.0 | C32—C33—C34 | 117.7 (6) |
C11—C10—C9 | 120.0 (5) | C32—C33—H33 | 121.2 |
C11—C10—H10 | 120.0 | C34—C33—H33 | 121.2 |
C9—C10—H10 | 120.0 | C33—C34—C29 | 122.8 (6) |
C12—C11—C10 | 120.0 (5) | C33—C34—H34 | 118.6 |
C12—C11—C15 | 120.0 (6) | C29—C34—H34 | 118.6 |
C10—C11—C15 | 120.0 (5) | O2—C35—H35A | 109.5 |
C11—C12—N2 | 120.0 (5) | O2—C35—H35B | 109.5 |
C11—C12—C7 | 120.0 (5) | H35A—C35—H35B | 109.5 |
N2—C12—C7 | 120.0 (5) | O2—C35—H35C | 109.5 |
N2—C13—C14 | 120.0 (6) | H35A—C35—H35C | 109.5 |
N2—C13—C16 | 119.6 (6) | H35B—C35—H35C | 109.5 |
C14—C13—C16 | 120.1 (6) | C1—N1—C5 | 115.3 (5) |
C13—C14—C15 | 120.0 (6) | C1—N1—Ru1 | 130.1 (4) |
C13—C14—H14 | 120.0 | C5—N1—Ru1 | 114.5 (4) |
C15—C14—H14 | 120.0 | C13—N2—C12 | 120.0 (5) |
C14—C15—C11 | 120.0 (6) | C13—N2—Ru1 | 130.9 (4) |
C14—C15—H15 | 120.0 | C12—N2—Ru1 | 109.1 (4) |
C11—C15—H15 | 120.0 | C7—O1—C6 | 118.9 (4) |
C13—C16—H16A | 109.5 | C7—O1—Ru1 | 113.9 (3) |
C13—C16—H16B | 109.5 | C6—O1—Ru1 | 111.9 (3) |
H16A—C16—H16B | 109.5 | C35—O2—H2A | 109.5 |
C13—C16—H16C | 109.5 | C29—P1—C23 | 101.2 (3) |
H16A—C16—H16C | 109.5 | C29—P1—C17 | 103.7 (3) |
H16B—C16—H16C | 109.5 | C23—P1—C17 | 101.1 (2) |
C18—C17—C22 | 119.7 (5) | C29—P1—Ru1 | 113.4 (2) |
C18—C17—P1 | 121.1 (4) | C23—P1—Ru1 | 117.07 (18) |
C22—C17—P1 | 119.0 (5) | C17—P1—Ru1 | 118.10 (17) |
C17—C18—C19 | 120.2 (5) | O1—Ru1—N1 | 79.47 (17) |
C17—C18—H18 | 119.9 | O1—Ru1—N2 | 79.66 (16) |
C19—C18—H18 | 119.9 | N1—Ru1—N2 | 158.25 (17) |
C20—C19—C18 | 118.5 (6) | O1—Ru1—P1 | 94.55 (11) |
C20—C19—H19 | 120.8 | N1—Ru1—P1 | 92.46 (12) |
C18—C19—H19 | 120.8 | N2—Ru1—P1 | 95.22 (13) |
C19—C20—C21 | 123.3 (6) | O1—Ru1—Cl2 | 169.80 (11) |
C19—C20—H20 | 118.4 | N1—Ru1—Cl2 | 92.40 (14) |
C21—C20—H20 | 118.4 | N2—Ru1—Cl2 | 107.61 (13) |
C20—C21—C22 | 120.2 (6) | P1—Ru1—Cl2 | 91.93 (6) |
C20—C21—H21 | 119.9 | O1—Ru1—Cl1 | 85.32 (11) |
C22—C21—H21 | 119.9 | N1—Ru1—Cl1 | 87.29 (12) |
C17—C22—C21 | 118.1 (6) | N2—Ru1—Cl1 | 84.98 (13) |
C17—C22—H22 | 121.0 | P1—Ru1—Cl1 | 179.74 (6) |
C21—C22—H22 | 121.0 | Cl2—Ru1—Cl1 | 88.17 (5) |
C24—C23—C28 | 117.9 (5) |
Experimental details
Crystal data | |
Chemical formula | [RuCl2(C16H14N2O)(C18H15P)]·CH4O |
Mr | 716.57 |
Crystal system, space group | Orthorhombic, P212121 |
Temperature (K) | 291 |
a, b, c (Å) | 8.868 (2), 11.480 (2), 31.6351 (18) |
V (Å3) | 3220.7 (10) |
Z | 4 |
Radiation type | Mo Kα |
µ (mm−1) | 0.74 |
Crystal size (mm) | 0.28 × 0.24 × 0.22 |
Data collection | |
Diffractometer | Bruker SMART APEX CCD |
Absorption correction | Multi-scan (SADABS; Sheldrick, 2003) |
Tmin, Tmax | 0.820, 0.855 |
No. of measured, independent and observed [I > 2σ(I)] reflections | 17669, 6304, 5620 |
Rint | 0.030 |
(sin θ/λ)max (Å−1) | 0.617 |
Refinement | |
R[F2 > 2σ(F2)], wR(F2), S | 0.049, 0.117, 1.10 |
No. of reflections | 6304 |
No. of parameters | 391 |
H-atom treatment | H-atom parameters constrained |
Δρmax, Δρmin (e Å−3) | 0.70, −0.91 |
Absolute structure | Flack (1983), 2722 Friedel pairs |
Absolute structure parameter | 0.06 (4) |
Computer programs: SMART (Bruker, 2003), SAINT-Plus (Bruker, 2003), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), SHELXTL (Sheldrick, 2008).
The N,O,N'-tridentate ligands with two pyridine-like donors and an ether donor are potentially a doubly chelating ligands in coordination chemistry. The presence of the flexible methylene and ether linkages allows the ligands to act as a folded N,N'-bidentate ligands or N,O,N'-tridentate ligands in meridional or facial arrangement, coordination to the metal coordinate (Al-Mandhary & Steel, 2003; Xu et al. 2009). Here, we report the synthesis and crystal structure of the title complex 1, [Ru(C16H14N2O)(PPh3)Cl2.CH3OH, which combines 2-methyl-8-(pyridineyl-2-methoxy)-quinoline and triphenylphosphane ligands. The molecular structure of the title compound is shown in Fig. 1. In the title complex 1, the ruthenium atom center is in a pseudooctahedral environment with the two nitrogen atoms and one oxygen atom which from 2-methyl-8-(pyridineyl-2-methoxy)-quinoline acts as a mer N,O,N'-tridentate ligand, two cis chlorine atoms and one phosphorus atom from PPh3 ligand trans to one chloride. The N—Ru—N angle is 158.25 (17)°. The N1—Ru—O1 and N2—Ru—O1 angles are 79.47 (17)° and 79.66 (16)°, respectively. The coordination between N,O,N'-tridentate ligand and the RuII yields two five-membered rings, RuN1C6C5O1 and RuO1C7C12N2. The Ru—Cl1 distance [2.4905 (14) Å], which is trans to the PPh3 ligand, is longer than the Ru—Cl2 distance [2.4104 (14) Å], similar differences are in agreement with reported value (Deng et al. 2005; Xu et al. 2009). The Ru—N(pyridine) [2.067 (5) Å], Ru—N(quinoline) [2.163 (5) Å], Ru—O [2.060 (3) Å] and Ru—P [2.2931 (15) Å] are similar to reported value (Deng et al. 2005; Xu et al. 2009).