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Supporting information
![]() | Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536810019276/tk2679sup1.cif |
![]() | Structure factor file (CIF format) https://doi.org/10.1107/S1600536810019276/tk2679Isup2.hkl |
CCDC reference: 698167
Key indicators
- Single-crystal X-ray study
- T = 293 K
- Mean
(C-C) = 0.005 Å
- R factor = 0.034
- wR factor = 0.078
- Data-to-parameter ratio = 16.8
checkCIF/PLATON results
No syntax errors found
Alert level C PLAT241_ALERT_2_C Check High Ueq as Compared to Neighbors for C133 PLAT242_ALERT_2_C Check Low Ueq as Compared to Neighbors for C3 PLAT420_ALERT_2_C D-H Without Acceptor N1 - H1N1 ... ? PLAT420_ALERT_2_C D-H Without Acceptor N1 - H2N1 ... ? PLAT420_ALERT_2_C D-H Without Acceptor N2 - H1N2 ... ? PLAT420_ALERT_2_C D-H Without Acceptor N2 - H2N2 ... ? PLAT048_ALERT_1_C MoietyFormula Not Given ........................ ?
Alert level G PLAT199_ALERT_1_G Check the Reported _cell_measurement_temperature 293 K PLAT200_ALERT_1_G Check the Reported _diffrn_ambient_temperature 293 K PLAT720_ALERT_4_G Number of Unusual/Non-Standard Labels .......... 4
0 ALERT level A = In general: serious problem 0 ALERT level B = Potentially serious problem 7 ALERT level C = Check and explain 3 ALERT level G = General alerts; check 3 ALERT type 1 CIF construction/syntax error, inconsistent or missing data 6 ALERT type 2 Indicator that the structure model may be wrong or deficient 0 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
All the reactions were performed using Schlenk-type flask under argon and standard high vacuum-line techniques. Solvents were of analytical grade and distilled under argon. The title compound was prepared starting from trans-RuCl2(PPh3)3 in a similar procedure described previously (Lindner et al., 2003b). Mixing of 2,2-dimethylpropane-1,3-diamine (0.059 ml, 0.49 mmol) in dichloromethane (10 ml) dropwise with trans-RuCl2(PPh3)3 (0.454 mmol) dissolved in the same solvent (15 ml). The reaction mixture was stirred at room temperature for 2 h. The solvent was removed in vacuo. Then the residue was washed well with hexane then diethylether and dried, to yield 310 mg (90%) of yellow powder. The recrystallization was performed by slow diffusion of diethylether into a solution of the complex in dichloromethane to yield orange-brown-plated crystals. 1H NMR (CD2Cl2): δ (p.p.m.) 0.79 (s, 6H, C(CH3)2), 2.57 (m, 4H, NCH2), 3.12 (br, s, 4H, NH2), 7.2–7.7 (m, 20H, C6H5). 31P{1H} NMR (CD2Cl2):δ (p.p.m.) 46.02 (s). 13C{1H} NMR (CD2Cl2): δ (p.p.m.) 25.3 (s, C(CH3)2), 34.2 (s, C(CH3)2), 49.2 (s, CH2N), 127.7 (t, N = 4.04 Hz, m-C6H5), 129.3 (s, p-C6H5), 135.4 (t, N=7.42 Hz,o-C6H5), 135.8 (d, N = 18.8 Hz, 1-C6H5). FAB MS: (m/z) 798.1 (M+). Anal. Calc. for C41H44Cl2N2P2Ru: C, 66.65.12; H, 5.55; Cl, 8.88; N, 3.51. Found: C, 66.94; H, 5.52; Cl, 9.20; N, 3.59%.
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 > 2sigma(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. All Hydrogen atoms were refined isotropically.All H atoms were fixed and subsequently refined using a riding model with Uiso(H) = 1.2Ueq of the carrier atom.
Data collection: CAD-4 EXPRESS (Enraf–Nonius, 1994); cell refinement: CAD-4 EXPRESS (Enraf–Nonius, 1994); data reduction: HELENA (Spek, 1996); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: PLATON (Spek, 2009); software used to prepare material for publication: XCIF in SHELXTL (Sheldrick, 2008).
![]() | Fig. 1. : The structure of the compound, showing 30% probability displacement ellipsoids and the atom numbering scheme. |
[RuCl2(C5H14N2)(C18H15P)2] | F(000) = 1648 |
Mr = 798.69 | Dx = 1.411 Mg m−3 |
Monoclinic, P21/c | Mo Kα radiation, λ = 0.70930 Å |
Hall symbol: -P 2ybc | Cell parameters from 25 reflections |
a = 17.393 (2) Å | θ = 7.8–12.3° |
b = 10.3493 (16) Å | µ = 0.68 mm−1 |
c = 21.315 (2) Å | T = 293 K |
β = 102.181 (15)° | Plate, brown |
V = 3750.4 (9) Å3 | 0.60 × 0.60 × 0.05 mm |
Z = 4 |
Enraf–Nonius CAD-4 diffractometer | 5387 reflections with I > 2σ(I) |
Radiation source: fine-focus sealed tube | Rint = 0.025 |
Graphite monochromator | θmax = 25.9°, θmin = 3.1° |
ω scans | h = −21→21 |
Absorption correction: ψ scan (North et al., 1968) | k = 0→12 |
Tmin = 0.687, Tmax = 0.967 | l = −1→26 |
7922 measured reflections | 3 standard reflections every 400 reflections |
7319 independent reflections | intensity decay: 2% |
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)] = 0.034 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.078 | Only H-atom coordinates refined |
S = 1.03 | w = 1/[σ2(Fo2) + (0.027P)2 + 1.9538P] where P = (Fo2 + 2Fc2)/3 |
7319 reflections | (Δ/σ)max = 0.001 |
436 parameters | Δρmax = 0.39 e Å−3 |
0 restraints | Δρmin = −0.51 e Å−3 |
[RuCl2(C5H14N2)(C18H15P)2] | V = 3750.4 (9) Å3 |
Mr = 798.69 | Z = 4 |
Monoclinic, P21/c | Mo Kα radiation |
a = 17.393 (2) Å | µ = 0.68 mm−1 |
b = 10.3493 (16) Å | T = 293 K |
c = 21.315 (2) Å | 0.60 × 0.60 × 0.05 mm |
β = 102.181 (15)° |
Enraf–Nonius CAD-4 diffractometer | 5387 reflections with I > 2σ(I) |
Absorption correction: ψ scan (North et al., 1968) | Rint = 0.025 |
Tmin = 0.687, Tmax = 0.967 | 3 standard reflections every 400 reflections |
7922 measured reflections | intensity decay: 2% |
7319 independent reflections |
R[F2 > 2σ(F2)] = 0.034 | 0 restraints |
wR(F2) = 0.078 | Only H-atom coordinates refined |
S = 1.03 | Δρmax = 0.39 e Å−3 |
7319 reflections | Δρmin = −0.51 e Å−3 |
436 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 | ||
Ru1 | 0.293247 (13) | 0.49329 (2) | 0.344643 (10) | 0.02586 (7) | |
Cl1 | 0.39278 (5) | 0.65793 (8) | 0.37293 (4) | 0.0421 (2) | |
Cl2 | 0.22021 (5) | 0.29446 (7) | 0.32284 (4) | 0.0424 (2) | |
P1 | 0.19157 (4) | 0.59121 (7) | 0.38125 (4) | 0.02806 (17) | |
C111 | 0.09258 (16) | 0.5977 (3) | 0.32882 (14) | 0.0316 (7) | |
C112 | 0.07724 (19) | 0.6794 (3) | 0.27611 (15) | 0.0386 (7) | |
H11A | 0.1169 | 0.7326 | 0.2675 | 0.046* | |
C113 | 0.0032 (2) | 0.6825 (3) | 0.23610 (17) | 0.0494 (9) | |
H11B | −0.0067 | 0.7391 | 0.2014 | 0.059* | |
C114 | −0.0553 (2) | 0.6028 (4) | 0.24725 (18) | 0.0520 (10) | |
H11C | −0.1048 | 0.6050 | 0.2202 | 0.062* | |
C115 | −0.04061 (19) | 0.5199 (4) | 0.29828 (18) | 0.0508 (9) | |
H11D | −0.0801 | 0.4647 | 0.3054 | 0.061* | |
C116 | 0.03250 (18) | 0.5174 (3) | 0.33944 (16) | 0.0417 (8) | |
H11E | 0.0415 | 0.4616 | 0.3744 | 0.050* | |
C121 | 0.20843 (17) | 0.7563 (3) | 0.41445 (14) | 0.0315 (7) | |
C122 | 0.2748 (2) | 0.7740 (3) | 0.46276 (16) | 0.0452 (8) | |
H12A | 0.3091 | 0.7052 | 0.4751 | 0.054* | |
C123 | 0.2907 (2) | 0.8923 (4) | 0.49275 (19) | 0.0559 (10) | |
H12B | 0.3345 | 0.9016 | 0.5261 | 0.067* | |
C124 | 0.2429 (2) | 0.9950 (4) | 0.47395 (19) | 0.0562 (10) | |
H12C | 0.2542 | 1.0745 | 0.4942 | 0.067* | |
C125 | 0.1782 (2) | 0.9815 (3) | 0.42524 (19) | 0.0547 (10) | |
H12D | 0.1461 | 1.0523 | 0.4116 | 0.066* | |
C126 | 0.1605 (2) | 0.8617 (3) | 0.39623 (16) | 0.0430 (8) | |
H12E | 0.1156 | 0.8526 | 0.3640 | 0.052* | |
C131 | 0.16632 (17) | 0.5131 (3) | 0.45301 (14) | 0.0350 (7) | |
C132 | 0.1386 (2) | 0.5845 (4) | 0.49815 (18) | 0.0578 (10) | |
H13A | 0.1363 | 0.6740 | 0.4942 | 0.069* | |
C133 | 0.1142 (3) | 0.5270 (4) | 0.5490 (2) | 0.0828 (16) | |
H13B | 0.0953 | 0.5775 | 0.5785 | 0.099* | |
C134 | 0.1179 (3) | 0.3955 (4) | 0.5561 (2) | 0.0754 (14) | |
H13C | 0.1028 | 0.3568 | 0.5909 | 0.090* | |
C135 | 0.1439 (2) | 0.3217 (4) | 0.5118 (2) | 0.0647 (11) | |
H13D | 0.1453 | 0.2322 | 0.5159 | 0.078* | |
C136 | 0.1682 (2) | 0.3799 (3) | 0.46079 (17) | 0.0485 (9) | |
H13E | 0.1861 | 0.3286 | 0.4311 | 0.058* | |
P2 | 0.26561 (4) | 0.57378 (7) | 0.23985 (4) | 0.02910 (17) | |
C211 | 0.17237 (18) | 0.5472 (3) | 0.18165 (14) | 0.0337 (7) | |
C212 | 0.1466 (2) | 0.6279 (4) | 0.12963 (17) | 0.0577 (10) | |
H21A | 0.1754 | 0.7014 | 0.1246 | 0.069* | |
C213 | 0.0781 (3) | 0.6003 (5) | 0.08490 (18) | 0.0713 (13) | |
H21B | 0.0607 | 0.6563 | 0.0507 | 0.086* | |
C214 | 0.0359 (2) | 0.4905 (4) | 0.09095 (17) | 0.0631 (11) | |
H21C | −0.0092 | 0.4708 | 0.0603 | 0.076* | |
C215 | 0.0604 (2) | 0.4106 (4) | 0.14206 (17) | 0.0536 (10) | |
H21D | 0.0321 | 0.3360 | 0.1463 | 0.064* | |
C216 | 0.1271 (2) | 0.4399 (3) | 0.18753 (16) | 0.0449 (8) | |
H21E | 0.1419 | 0.3862 | 0.2230 | 0.054* | |
C221 | 0.28413 (18) | 0.7468 (3) | 0.22798 (15) | 0.0344 (7) | |
C222 | 0.26872 (18) | 0.8358 (3) | 0.27232 (16) | 0.0405 (8) | |
H22A | 0.2537 | 0.8066 | 0.3092 | 0.049* | |
C223 | 0.2753 (2) | 0.9669 (3) | 0.2627 (2) | 0.0540 (10) | |
H22B | 0.2638 | 1.0251 | 0.2927 | 0.065* | |
C224 | 0.2986 (3) | 1.0114 (4) | 0.2091 (2) | 0.0687 (12) | |
H22C | 0.3029 | 1.0997 | 0.2025 | 0.082* | |
C225 | 0.3156 (3) | 0.9248 (4) | 0.1651 (2) | 0.0714 (13) | |
H22D | 0.3320 | 0.9549 | 0.1290 | 0.086* | |
C226 | 0.3088 (2) | 0.7939 (3) | 0.17389 (18) | 0.0527 (9) | |
H22E | 0.3206 | 0.7364 | 0.1437 | 0.063* | |
C231 | 0.33381 (18) | 0.4979 (3) | 0.19493 (14) | 0.0372 (7) | |
C232 | 0.4127 (2) | 0.5332 (4) | 0.20829 (18) | 0.0529 (10) | |
H23A | 0.4294 | 0.6053 | 0.2336 | 0.063* | |
C233 | 0.4668 (2) | 0.4602 (5) | 0.1836 (2) | 0.0725 (14) | |
H23B | 0.5197 | 0.4830 | 0.1930 | 0.087* | |
C234 | 0.4424 (3) | 0.3548 (5) | 0.1456 (2) | 0.0802 (15) | |
H23C | 0.4788 | 0.3063 | 0.1293 | 0.096* | |
C235 | 0.3650 (3) | 0.3213 (4) | 0.1316 (2) | 0.0735 (13) | |
H23D | 0.3486 | 0.2506 | 0.1052 | 0.088* | |
C236 | 0.3109 (2) | 0.3911 (3) | 0.15613 (16) | 0.0495 (9) | |
H23E | 0.2583 | 0.3665 | 0.1466 | 0.059* | |
N1 | 0.38992 (15) | 0.3781 (3) | 0.32350 (12) | 0.0411 (7) | |
H1N1 | 0.3780 | 0.3623 | 0.2810 | 0.049* | |
H2N1 | 0.4325 | 0.4298 | 0.3306 | 0.049* | |
N2 | 0.34248 (15) | 0.4290 (3) | 0.44251 (12) | 0.0383 (6) | |
H1N2 | 0.3807 | 0.4856 | 0.4590 | 0.046* | |
H2N2 | 0.3043 | 0.4393 | 0.4647 | 0.046* | |
C1 | 0.4154 (2) | 0.2550 (3) | 0.35469 (16) | 0.0489 (9) | |
H1B | 0.4582 | 0.2214 | 0.3369 | 0.059* | |
H1C | 0.3722 | 0.1941 | 0.3445 | 0.059* | |
C2 | 0.3752 (2) | 0.3010 (4) | 0.45837 (17) | 0.0549 (10) | |
H2B | 0.3332 | 0.2382 | 0.4463 | 0.066* | |
H2C | 0.3934 | 0.2959 | 0.5046 | 0.066* | |
C3 | 0.4423 (2) | 0.2623 (3) | 0.42720 (15) | 0.0434 (8) | |
C4 | 0.5121 (2) | 0.3503 (4) | 0.44572 (19) | 0.0664 (12) | |
H4A | 0.4975 | 0.4364 | 0.4311 | 0.100* | |
H4B | 0.5539 | 0.3203 | 0.4263 | 0.100* | |
H4C | 0.5296 | 0.3505 | 0.4916 | 0.100* | |
C5 | 0.4653 (3) | 0.1253 (4) | 0.4505 (2) | 0.0764 (14) | |
H5A | 0.4828 | 0.1255 | 0.4963 | 0.115* | |
H5B | 0.5070 | 0.0950 | 0.4311 | 0.115* | |
H5C | 0.4206 | 0.0693 | 0.4386 | 0.115* |
U11 | U22 | U33 | U12 | U13 | U23 | |
Ru1 | 0.02516 (11) | 0.02601 (12) | 0.02646 (11) | 0.00136 (11) | 0.00557 (8) | 0.00011 (11) |
Cl1 | 0.0348 (4) | 0.0439 (5) | 0.0458 (5) | −0.0102 (4) | 0.0044 (3) | 0.0005 (4) |
Cl2 | 0.0489 (5) | 0.0297 (4) | 0.0447 (5) | −0.0058 (4) | 0.0014 (4) | −0.0002 (3) |
P1 | 0.0275 (4) | 0.0273 (4) | 0.0300 (4) | 0.0013 (3) | 0.0073 (3) | −0.0002 (3) |
C111 | 0.0276 (15) | 0.0320 (16) | 0.0358 (16) | 0.0038 (13) | 0.0082 (13) | −0.0051 (13) |
C112 | 0.0390 (18) | 0.0373 (18) | 0.0391 (18) | 0.0005 (15) | 0.0074 (14) | −0.0027 (15) |
C113 | 0.051 (2) | 0.045 (2) | 0.046 (2) | 0.0098 (18) | −0.0050 (17) | 0.0030 (17) |
C114 | 0.0343 (18) | 0.058 (2) | 0.058 (2) | 0.0082 (18) | −0.0039 (17) | −0.014 (2) |
C115 | 0.0355 (17) | 0.058 (2) | 0.058 (2) | −0.0098 (17) | 0.0094 (16) | −0.007 (2) |
C116 | 0.0353 (16) | 0.046 (2) | 0.0440 (18) | −0.0061 (16) | 0.0079 (14) | −0.0025 (16) |
C121 | 0.0353 (16) | 0.0287 (15) | 0.0336 (17) | 0.0016 (13) | 0.0144 (13) | −0.0014 (13) |
C122 | 0.0430 (19) | 0.0414 (19) | 0.049 (2) | 0.0038 (16) | 0.0040 (16) | −0.0042 (16) |
C123 | 0.050 (2) | 0.055 (2) | 0.059 (2) | −0.0112 (19) | 0.0025 (18) | −0.018 (2) |
C124 | 0.065 (2) | 0.0357 (19) | 0.071 (3) | −0.011 (2) | 0.021 (2) | −0.022 (2) |
C125 | 0.069 (2) | 0.0305 (19) | 0.066 (2) | 0.0093 (18) | 0.017 (2) | −0.0052 (18) |
C126 | 0.0421 (19) | 0.0397 (19) | 0.046 (2) | 0.0055 (15) | 0.0079 (16) | −0.0052 (16) |
C131 | 0.0325 (15) | 0.0392 (18) | 0.0349 (15) | −0.0011 (15) | 0.0105 (12) | 0.0021 (15) |
C132 | 0.087 (3) | 0.041 (2) | 0.059 (2) | −0.005 (2) | 0.044 (2) | −0.0039 (18) |
C133 | 0.137 (4) | 0.057 (3) | 0.077 (3) | −0.013 (3) | 0.076 (3) | −0.008 (2) |
C134 | 0.108 (4) | 0.068 (3) | 0.064 (3) | −0.005 (3) | 0.051 (3) | 0.012 (2) |
C135 | 0.081 (3) | 0.047 (2) | 0.077 (3) | 0.006 (2) | 0.041 (2) | 0.017 (2) |
C136 | 0.060 (2) | 0.0385 (19) | 0.055 (2) | 0.0082 (17) | 0.0294 (19) | 0.0069 (17) |
P2 | 0.0320 (4) | 0.0273 (4) | 0.0286 (4) | 0.0006 (3) | 0.0079 (3) | 0.0012 (3) |
C211 | 0.0368 (17) | 0.0363 (16) | 0.0278 (15) | 0.0032 (14) | 0.0064 (13) | −0.0006 (13) |
C212 | 0.058 (2) | 0.060 (2) | 0.047 (2) | −0.013 (2) | −0.0066 (18) | 0.0191 (19) |
C213 | 0.076 (3) | 0.086 (3) | 0.041 (2) | −0.011 (3) | −0.013 (2) | 0.025 (2) |
C214 | 0.056 (2) | 0.087 (3) | 0.040 (2) | −0.015 (2) | −0.0045 (17) | 0.001 (2) |
C215 | 0.049 (2) | 0.059 (2) | 0.050 (2) | −0.0125 (19) | 0.0036 (18) | −0.0034 (19) |
C216 | 0.045 (2) | 0.048 (2) | 0.0402 (19) | −0.0032 (17) | 0.0053 (16) | 0.0029 (16) |
C221 | 0.0362 (17) | 0.0280 (16) | 0.0389 (18) | −0.0026 (13) | 0.0075 (14) | 0.0050 (14) |
C222 | 0.0386 (18) | 0.0346 (17) | 0.047 (2) | −0.0010 (15) | 0.0074 (15) | 0.0031 (15) |
C223 | 0.061 (2) | 0.0294 (19) | 0.071 (3) | −0.0024 (16) | 0.012 (2) | −0.0012 (17) |
C224 | 0.088 (3) | 0.031 (2) | 0.087 (3) | −0.007 (2) | 0.020 (3) | 0.017 (2) |
C225 | 0.099 (3) | 0.049 (2) | 0.074 (3) | −0.006 (2) | 0.035 (3) | 0.023 (2) |
C226 | 0.071 (3) | 0.041 (2) | 0.050 (2) | 0.0000 (19) | 0.0215 (19) | 0.0081 (17) |
C231 | 0.0444 (17) | 0.0372 (16) | 0.0345 (16) | 0.0093 (17) | 0.0184 (13) | 0.0109 (16) |
C232 | 0.052 (2) | 0.054 (2) | 0.058 (2) | 0.0082 (18) | 0.0243 (18) | 0.0162 (18) |
C233 | 0.051 (2) | 0.089 (4) | 0.089 (3) | 0.017 (2) | 0.040 (2) | 0.039 (3) |
C234 | 0.099 (4) | 0.068 (3) | 0.092 (4) | 0.039 (3) | 0.063 (3) | 0.022 (3) |
C235 | 0.108 (4) | 0.061 (3) | 0.064 (3) | 0.023 (3) | 0.047 (3) | −0.002 (2) |
C236 | 0.068 (2) | 0.044 (2) | 0.042 (2) | 0.0088 (19) | 0.0224 (18) | 0.0015 (16) |
N1 | 0.0444 (16) | 0.0454 (16) | 0.0353 (15) | 0.0172 (13) | 0.0121 (12) | 0.0037 (13) |
N2 | 0.0378 (15) | 0.0464 (16) | 0.0313 (14) | 0.0102 (13) | 0.0090 (11) | 0.0033 (12) |
C1 | 0.058 (2) | 0.043 (2) | 0.045 (2) | 0.0169 (18) | 0.0098 (17) | 0.0024 (17) |
C2 | 0.071 (3) | 0.056 (2) | 0.040 (2) | 0.023 (2) | 0.0158 (18) | 0.0165 (18) |
C3 | 0.0454 (19) | 0.046 (2) | 0.0381 (18) | 0.0177 (16) | 0.0075 (15) | 0.0056 (16) |
C4 | 0.046 (2) | 0.087 (3) | 0.061 (3) | 0.007 (2) | 0.0016 (19) | −0.003 (2) |
C5 | 0.102 (4) | 0.064 (3) | 0.066 (3) | 0.039 (3) | 0.022 (3) | 0.020 (2) |
Ru1—N1 | 2.184 (2) | C213—C214 | 1.374 (6) |
Ru1—N2 | 2.185 (2) | C213—H21B | 0.9300 |
Ru1—P1 | 2.3120 (8) | C214—C215 | 1.362 (5) |
Ru1—P2 | 2.3370 (8) | C214—H21C | 0.9300 |
Ru1—Cl2 | 2.4114 (8) | C215—C216 | 1.379 (5) |
Ru1—Cl1 | 2.4131 (8) | C215—H21D | 0.9300 |
P1—C111 | 1.845 (3) | C216—H21E | 0.9300 |
P1—C121 | 1.849 (3) | C221—C222 | 1.385 (4) |
P1—C131 | 1.863 (3) | C221—C226 | 1.400 (4) |
C111—C112 | 1.387 (4) | C222—C223 | 1.381 (4) |
C111—C116 | 1.390 (4) | C222—H22A | 0.9300 |
C112—C113 | 1.386 (4) | C223—C224 | 1.371 (5) |
C112—H11A | 0.9300 | C223—H22B | 0.9300 |
C113—C114 | 1.370 (5) | C224—C225 | 1.374 (6) |
C113—H11B | 0.9300 | C224—H22C | 0.9300 |
C114—C115 | 1.366 (5) | C225—C226 | 1.376 (5) |
C114—H11C | 0.9300 | C225—H22D | 0.9300 |
C115—C116 | 1.384 (4) | C226—H22E | 0.9300 |
C115—H11D | 0.9300 | C231—C236 | 1.387 (5) |
C116—H11E | 0.9300 | C231—C232 | 1.391 (5) |
C121—C126 | 1.377 (4) | C232—C233 | 1.393 (5) |
C121—C122 | 1.388 (4) | C232—H23A | 0.9300 |
C122—C123 | 1.382 (5) | C233—C234 | 1.371 (7) |
C122—H12A | 0.9300 | C233—H23B | 0.9300 |
C123—C124 | 1.356 (5) | C234—C235 | 1.361 (7) |
C123—H12B | 0.9300 | C234—H23C | 0.9300 |
C124—C125 | 1.368 (5) | C235—C236 | 1.375 (5) |
C124—H12C | 0.9300 | C235—H23D | 0.9300 |
C125—C126 | 1.391 (5) | C236—H23E | 0.9300 |
C125—H12D | 0.9300 | N1—C1 | 1.461 (4) |
C126—H12E | 0.9300 | N1—H1N1 | 0.9000 |
C131—C132 | 1.378 (4) | N1—H2N1 | 0.9000 |
C131—C136 | 1.387 (4) | N2—C2 | 1.453 (4) |
C132—C133 | 1.380 (5) | N2—H1N2 | 0.9000 |
C132—H13A | 0.9300 | N2—H2N2 | 0.9000 |
C133—C134 | 1.369 (6) | C1—C3 | 1.520 (4) |
C133—H13B | 0.9300 | C1—H1B | 0.9700 |
C134—C135 | 1.363 (5) | C1—H1C | 0.9700 |
C134—H13C | 0.9300 | C2—C3 | 1.514 (5) |
C135—C136 | 1.386 (5) | C2—H2B | 0.9700 |
C135—H13D | 0.9300 | C2—H2C | 0.9700 |
C136—H13E | 0.9300 | C3—C4 | 1.502 (5) |
P2—C211 | 1.843 (3) | C3—C5 | 1.527 (5) |
P2—C221 | 1.846 (3) | C4—H4A | 0.9600 |
P2—C231 | 1.849 (3) | C4—H4B | 0.9600 |
C211—C216 | 1.383 (4) | C4—H4C | 0.9600 |
C211—C212 | 1.385 (4) | C5—H5A | 0.9600 |
C212—C213 | 1.389 (5) | C5—H5B | 0.9600 |
C212—H21A | 0.9300 | C5—H5C | 0.9600 |
N1—Ru1—N2 | 82.35 (9) | C212—C213—H21B | 119.9 |
N1—Ru1—P1 | 170.31 (7) | C215—C214—C213 | 119.6 (3) |
N2—Ru1—P1 | 89.14 (7) | C215—C214—H21C | 120.2 |
N1—Ru1—P2 | 90.54 (7) | C213—C214—H21C | 120.2 |
N2—Ru1—P2 | 168.90 (7) | C214—C215—C216 | 120.3 (4) |
P1—Ru1—P2 | 98.55 (3) | C214—C215—H21D | 119.9 |
N1—Ru1—Cl2 | 83.77 (8) | C216—C215—H21D | 119.9 |
N2—Ru1—Cl2 | 90.48 (8) | C215—C216—C211 | 121.6 (3) |
P1—Ru1—Cl2 | 91.70 (3) | C215—C216—H21E | 119.2 |
P2—Ru1—Cl2 | 97.25 (3) | C211—C216—H21E | 119.2 |
N1—Ru1—Cl1 | 83.92 (8) | C222—C221—C226 | 117.9 (3) |
N2—Ru1—Cl1 | 81.99 (8) | C222—C221—P2 | 119.1 (2) |
P1—Ru1—Cl1 | 99.54 (3) | C226—C221—P2 | 122.9 (3) |
P2—Ru1—Cl1 | 88.81 (3) | C223—C222—C221 | 121.2 (3) |
Cl2—Ru1—Cl1 | 166.33 (3) | C223—C222—H22A | 119.4 |
C111—P1—C121 | 104.52 (14) | C221—C222—H22A | 119.4 |
C111—P1—C131 | 99.29 (13) | C224—C223—C222 | 120.2 (4) |
C121—P1—C131 | 97.63 (14) | C224—C223—H22B | 119.9 |
C111—P1—Ru1 | 119.59 (9) | C222—C223—H22B | 119.9 |
C121—P1—Ru1 | 117.61 (10) | C223—C224—C225 | 119.6 (4) |
C131—P1—Ru1 | 114.61 (10) | C223—C224—H22C | 120.2 |
C112—C111—C116 | 118.3 (3) | C225—C224—H22C | 120.2 |
C112—C111—P1 | 120.5 (2) | C224—C225—C226 | 120.8 (4) |
C116—C111—P1 | 121.1 (2) | C224—C225—H22D | 119.6 |
C113—C112—C111 | 120.5 (3) | C226—C225—H22D | 119.6 |
C113—C112—H11A | 119.8 | C225—C226—C221 | 120.3 (4) |
C111—C112—H11A | 119.8 | C225—C226—H22E | 119.8 |
C114—C113—C112 | 120.5 (3) | C221—C226—H22E | 119.8 |
C114—C113—H11B | 119.8 | C236—C231—C232 | 118.6 (3) |
C112—C113—H11B | 119.8 | C236—C231—P2 | 120.8 (3) |
C115—C114—C113 | 119.7 (3) | C232—C231—P2 | 119.7 (3) |
C115—C114—H11C | 120.1 | C231—C232—C233 | 119.7 (4) |
C113—C114—H11C | 120.1 | C231—C232—H23A | 120.1 |
C114—C115—C116 | 120.6 (3) | C233—C232—H23A | 120.1 |
C114—C115—H11D | 119.7 | C234—C233—C232 | 120.3 (4) |
C116—C115—H11D | 119.7 | C234—C233—H23B | 119.8 |
C115—C116—C111 | 120.5 (3) | C232—C233—H23B | 119.8 |
C115—C116—H11E | 119.8 | C235—C234—C233 | 120.1 (4) |
C111—C116—H11E | 119.8 | C235—C234—H23C | 120.0 |
C126—C121—C122 | 117.7 (3) | C233—C234—H23C | 120.0 |
C126—C121—P1 | 125.9 (2) | C234—C235—C236 | 120.5 (4) |
C122—C121—P1 | 116.5 (2) | C234—C235—H23D | 119.7 |
C123—C122—C121 | 120.9 (3) | C236—C235—H23D | 119.7 |
C123—C122—H12A | 119.6 | C235—C236—C231 | 120.8 (4) |
C121—C122—H12A | 119.6 | C235—C236—H23E | 119.6 |
C124—C123—C122 | 120.5 (3) | C231—C236—H23E | 119.6 |
C124—C123—H12B | 119.8 | C1—N1—Ru1 | 123.7 (2) |
C122—C123—H12B | 119.8 | C1—N1—H1N1 | 106.4 |
C123—C124—C125 | 120.0 (3) | Ru1—N1—H1N1 | 106.4 |
C123—C124—H12C | 120.0 | C1—N1—H2N1 | 106.4 |
C125—C124—H12C | 120.0 | Ru1—N1—H2N1 | 106.4 |
C124—C125—C126 | 119.8 (3) | H1N1—N1—H2N1 | 106.5 |
C124—C125—H12D | 120.1 | C2—N2—Ru1 | 123.7 (2) |
C126—C125—H12D | 120.1 | C2—N2—H1N2 | 106.4 |
C121—C126—C125 | 121.1 (3) | Ru1—N2—H1N2 | 106.4 |
C121—C126—H12E | 119.4 | C2—N2—H2N2 | 106.4 |
C125—C126—H12E | 119.4 | Ru1—N2—H2N2 | 106.4 |
C132—C131—C136 | 116.9 (3) | H1N2—N2—H2N2 | 106.5 |
C132—C131—P1 | 121.2 (3) | N1—C1—C3 | 114.7 (3) |
C136—C131—P1 | 121.7 (2) | N1—C1—H1B | 108.6 |
C131—C132—C133 | 121.8 (4) | C3—C1—H1B | 108.6 |
C131—C132—H13A | 119.1 | N1—C1—H1C | 108.6 |
C133—C132—H13A | 119.1 | C3—C1—H1C | 108.6 |
C134—C133—C132 | 120.0 (4) | H1B—C1—H1C | 107.6 |
C134—C133—H13B | 120.0 | N2—C2—C3 | 116.1 (3) |
C132—C133—H13B | 120.0 | N2—C2—H2B | 108.3 |
C135—C134—C133 | 119.7 (4) | C3—C2—H2B | 108.3 |
C135—C134—H13C | 120.1 | N2—C2—H2C | 108.3 |
C133—C134—H13C | 120.1 | C3—C2—H2C | 108.3 |
C134—C135—C136 | 120.0 (4) | H2B—C2—H2C | 107.4 |
C134—C135—H13D | 120.0 | C4—C3—C2 | 112.3 (3) |
C136—C135—H13D | 120.0 | C4—C3—C1 | 110.9 (3) |
C135—C136—C131 | 121.5 (3) | C2—C3—C1 | 111.0 (3) |
C135—C136—H13E | 119.2 | C4—C3—C5 | 109.6 (3) |
C131—C136—H13E | 119.2 | C2—C3—C5 | 106.1 (3) |
C211—P2—C221 | 101.92 (14) | C1—C3—C5 | 106.7 (3) |
C211—P2—C231 | 99.08 (14) | C3—C4—H4A | 109.5 |
C221—P2—C231 | 101.03 (14) | C3—C4—H4B | 109.5 |
C211—P2—Ru1 | 124.38 (10) | H4A—C4—H4B | 109.5 |
C221—P2—Ru1 | 118.04 (10) | C3—C4—H4C | 109.5 |
C231—P2—Ru1 | 108.57 (10) | H4A—C4—H4C | 109.5 |
C216—C211—C212 | 117.5 (3) | H4B—C4—H4C | 109.5 |
C216—C211—P2 | 119.7 (2) | C3—C5—H5A | 109.5 |
C212—C211—P2 | 122.7 (3) | C3—C5—H5B | 109.5 |
C211—C212—C213 | 120.8 (4) | H5A—C5—H5B | 109.5 |
C211—C212—H21A | 119.6 | C3—C5—H5C | 109.5 |
C213—C212—H21A | 119.6 | H5A—C5—H5C | 109.5 |
C214—C213—C212 | 120.3 (4) | H5B—C5—H5C | 109.5 |
C214—C213—H21B | 119.9 |
Experimental details
Crystal data | |
Chemical formula | [RuCl2(C5H14N2)(C18H15P)2] |
Mr | 798.69 |
Crystal system, space group | Monoclinic, P21/c |
Temperature (K) | 293 |
a, b, c (Å) | 17.393 (2), 10.3493 (16), 21.315 (2) |
β (°) | 102.181 (15) |
V (Å3) | 3750.4 (9) |
Z | 4 |
Radiation type | Mo Kα |
µ (mm−1) | 0.68 |
Crystal size (mm) | 0.60 × 0.60 × 0.05 |
Data collection | |
Diffractometer | Enraf–Nonius CAD-4 diffractometer |
Absorption correction | ψ scan (North et al., 1968) |
Tmin, Tmax | 0.687, 0.967 |
No. of measured, independent and observed [I > 2σ(I)] reflections | 7922, 7319, 5387 |
Rint | 0.025 |
(sin θ/λ)max (Å−1) | 0.616 |
Refinement | |
R[F2 > 2σ(F2)], wR(F2), S | 0.034, 0.078, 1.03 |
No. of reflections | 7319 |
No. of parameters | 436 |
H-atom treatment | Only H-atom coordinates refined |
Δρmax, Δρmin (e Å−3) | 0.39, −0.51 |
Computer programs: CAD-4 EXPRESS (Enraf–Nonius, 1994), HELENA (Spek, 1996), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), PLATON (Spek, 2009), XCIF in SHELXTL (Sheldrick, 2008).
One of the important transformations in the organic synthesis is the reduction of ketones to secondary alcohol (Noyori, 1994). The enantioselective hydrogenation of prochiral carbonyl compounds to chiral alcohols is among the most valuable method in organic chemistry (Drozdzak et al., 2005; Lindner et al., 2005). Furthermore, stereo-, regio- and enantioselective ruthenium-catalysis lies at the heart of current developments in pharmaceutical, agrochemical and similar industries (Noyori, 2003; Clarke, 2002). Recently Noyori et al. (Ohkuma et al., 2002; Noyori & Ohkuma, 2001) discovered a ruthenium(II) complex system containing diphosphine and 1,2-diamine ligands which, in the presence of a base and 2-propanol, proved to be excellent catalysts (regarding efficiency, enantioselectivity, and flexibility) for the hydrogenation of ketones under mild conditions (Lindner et al., 2005; Noyori & Ohkuma, 2001). The title complex is crystallized as free solvated trans-dichloro-cis-bis(triphenylphosphane) isomer with approximate C2v symmetry. The ruthenium atom is coordinated with two chlorine species in trans form, one diamine co-ligand via the nitrogen atoms and two triphenylphosphane ligands via the phosphorus atoms in cis forms. The complex exhibits distorted octahedron geometry around the ruthenium center atom with two Ru–N distances of 2.183 (3)Å and 2.185 (3) Å, two Ru–Cl distances of 2.4114 (8)Å and 2.4130 (8)Å and two Ru–P distances equal 2.3120 (8)Å and 2.3370 (8) Å. The diamine and phosphine ligands are practically planar. The coordination angle of the diamine chelate ring results in distinctly N–Ru–N angle of 82.35 (11)° departs from ideal value by up to approximately 7.6°, due to the six-membered ring chelating nature of 1,3-propanediamine ligand, while the P–Ru–P angle is equal 98.55 (3)°. The dichloro ligands are bent away from their axial positions toward the diamine ligand forming Cl–Ru–Cl angle of 166.32 (3)°, resonating to the steric effect of the phenyls in the phosphine ligands. In the crystal structure there are a number of RuCl···HN contacts smaller than 3.0 Å, indicating the presence of unconventional intra-hydrogen bonds (Doucet et al., 1998; Warad et al., 2006).