In the title compound, [RuCl2(C27H33O3P)(C6H6)]·CH2Cl2, the Ru—P bond distance is 2.2790 (4) Å, and the Ru—Cl bond distances are 2.4052 (4) and 2.4046 (4) Å. The title compound is the first reported structure containing tris(2-isopropylphenyl)phosphite as a ligand. The effective cone angle (θE) for the tris(2-isopropylphenyl) phosphite was calculated to be 160°.
Supporting information
CCDC reference: 618213
Key indicators
- Single-crystal X-ray study
- T = 150 K
- Mean (C-C) = 0.003 Å
- R factor = 0.023
- wR factor = 0.058
- Data-to-parameter ratio = 21.8
checkCIF/PLATON results
No syntax errors found
Alert level C
PLAT220_ALERT_2_C Large Non-Solvent C Ueq(max)/Ueq(min) ... 3.03 Ratio
PLAT222_ALERT_3_C Large Non-Solvent H Ueq(max)/Ueq(min) ... 3.28 Ratio
PLAT232_ALERT_2_C Hirshfeld Test Diff (M-X) Ru - Cl1 .. 5.07 su
PLAT232_ALERT_2_C Hirshfeld Test Diff (M-X) Ru - Cl2 .. 5.57 su
PLAT720_ALERT_4_C Number of Unusual/Non-Standard Label(s) ........ 2
0 ALERT level A = In general: serious problem
0 ALERT level B = Potentially serious problem
5 ALERT level C = Check and explain
0 ALERT level G = General alerts; check
0 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
3 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
Data collection: APEX2 (Bruker, 2005); cell refinement: SAINT-Plus (Bruker, 2004); data reduction: SAINT-Plus and XPREP (Bruker, 2004); program(s) used to solve structure: SIR97 (Altomare et al., 1999); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: DIAMOND (Brandenburg & Putz, 2005); software used to prepare material for publication: WinGX (Farrugia, 1999).
(
η6-Benzene)dichloro[tris(2-isopropylphenyl)phosphite]ruthenium(II)
dichloromethane solvate
top
Crystal data top
[RuCl2(C27H33O3P)(C6H6)]·CH2Cl2 | F(000) = 1584 |
Mr = 771.51 | Dx = 1.483 Mg m−3 |
Monoclinic, P21/n | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: -P 2yn | Cell parameters from 8690 reflections |
a = 10.7593 (6) Å | θ = 2.3–28.3° |
b = 18.6163 (11) Å | µ = 0.84 mm−1 |
c = 17.5744 (10) Å | T = 150 K |
β = 101.029 (2)° | Cuboid, red |
V = 3455.1 (3) Å3 | 0.3 × 0.28 × 0.19 mm |
Z = 4 | |
Data collection top
Bruker X8 APEX-II 4K Kappa-CCD diffractometer | 8585 independent reflections |
Radiation source: fine-focus sealed tube | 7855 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.038 |
Detector resolution: 512 pixels mm-1 | θmax = 28.3°, θmin = 2.1° |
ω and φ scans | h = −14→14 |
Absorption correction: multi-scan (SADABS; Bruker, 2004) | k = −24→24 |
Tmin = 0.786, Tmax = 0.856 | l = −23→23 |
80414 measured reflections | |
Refinement top
Refinement on F2 | 0 restraints |
Least-squares matrix: full | H-atom parameters constrained |
R[F2 > 2σ(F2)] = 0.023 | w = 1/[σ2(Fo2) + (0.021P)2 + 2.6184P] where P = (Fo2 + 2Fc2)/3 |
wR(F2) = 0.058 | (Δ/σ)max = 0.001 |
S = 1.06 | Δρmax = 0.78 e Å−3 |
8585 reflections | Δρmin = −0.88 e Å−3 |
394 parameters | |
Special details top
Experimental. The intensity data was collected on a Bruker X8 Apex II 4 K Kappa CCD
diffractometer using an exposure time of 10 s/frame. A total of 2539 frames
were collected with a frame width of 0.5° covering up to θ = 28.28° with
100% completeness accomplished. |
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. |
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top | x | y | z | Uiso*/Ueq | |
Ru | 0.934199 (10) | 0.133029 (6) | 0.564731 (6) | 0.01389 (4) | |
P | 0.98307 (3) | 0.239182 (19) | 0.62799 (2) | 0.01357 (7) | |
Cl1 | 1.09269 (3) | 0.15674 (2) | 0.48827 (2) | 0.02059 (7) | |
Cl2 | 1.09729 (3) | 0.084531 (19) | 0.66431 (2) | 0.02110 (7) | |
O1 | 0.99838 (9) | 0.24282 (6) | 0.71995 (6) | 0.0170 (2) | |
C11 | 0.90528 (14) | 0.22618 (9) | 0.76374 (8) | 0.0202 (3) | |
C12 | 0.85013 (15) | 0.28331 (10) | 0.79695 (9) | 0.0254 (3) | |
C13 | 0.76432 (17) | 0.26453 (12) | 0.84406 (11) | 0.0376 (4) | |
H13 | 0.7239 | 0.3015 | 0.8675 | 0.045* | |
C14 | 0.73660 (19) | 0.19381 (14) | 0.85751 (11) | 0.0434 (5) | |
H14 | 0.6771 | 0.1829 | 0.8894 | 0.052* | |
C15 | 0.79477 (18) | 0.13866 (12) | 0.82485 (11) | 0.0363 (4) | |
H15 | 0.7758 | 0.09 | 0.8344 | 0.044* | |
C16 | 0.88143 (15) | 0.15512 (10) | 0.77787 (9) | 0.0254 (3) | |
H16 | 0.9236 | 0.1179 | 0.7558 | 0.03* | |
C1 | 0.89036 (17) | 0.35978 (10) | 0.78590 (10) | 0.0295 (4) | |
H1 | 0.8975 | 0.3657 | 0.7303 | 0.035* | |
C2 | 1.02144 (19) | 0.37333 (11) | 0.83578 (12) | 0.0396 (5) | |
H2A | 1.0177 | 0.3661 | 0.8905 | 0.059* | |
H2B | 1.0478 | 0.4228 | 0.828 | 0.059* | |
H2C | 1.0827 | 0.3398 | 0.8207 | 0.059* | |
C3 | 0.7972 (2) | 0.41618 (12) | 0.80429 (13) | 0.0474 (5) | |
H3A | 0.7123 | 0.4057 | 0.7746 | 0.071* | |
H3B | 0.8239 | 0.4639 | 0.7902 | 0.071* | |
H3C | 0.7956 | 0.4151 | 0.8598 | 0.071* | |
O2 | 0.88195 (10) | 0.30373 (6) | 0.60637 (6) | 0.0183 (2) | |
C21 | 0.82545 (14) | 0.32286 (8) | 0.53041 (8) | 0.0181 (3) | |
C22 | 0.69948 (15) | 0.34536 (9) | 0.51827 (9) | 0.0234 (3) | |
C23 | 0.64245 (17) | 0.36115 (10) | 0.44172 (10) | 0.0301 (4) | |
H23 | 0.5563 | 0.3759 | 0.4309 | 0.036* | |
C24 | 0.70761 (18) | 0.35598 (10) | 0.38132 (10) | 0.0303 (4) | |
H24 | 0.6658 | 0.3661 | 0.3298 | 0.036* | |
C25 | 0.83365 (17) | 0.33608 (9) | 0.39616 (9) | 0.0262 (3) | |
H25 | 0.8794 | 0.3343 | 0.355 | 0.031* | |
C26 | 0.89349 (15) | 0.31871 (8) | 0.47105 (9) | 0.0209 (3) | |
H26 | 0.9797 | 0.3042 | 0.4815 | 0.025* | |
C4 | 0.62668 (17) | 0.35303 (11) | 0.58369 (11) | 0.0317 (4) | |
H4 | 0.6789 | 0.3311 | 0.6312 | 0.038* | |
C5 | 0.4999 (2) | 0.31347 (15) | 0.56651 (15) | 0.0545 (6) | |
H5A | 0.4446 | 0.336 | 0.5222 | 0.082* | |
H5B | 0.4597 | 0.3159 | 0.612 | 0.082* | |
H5C | 0.5141 | 0.2631 | 0.5544 | 0.082* | |
C6 | 0.6079 (3) | 0.43192 (13) | 0.60049 (15) | 0.0548 (6) | |
H6A | 0.6904 | 0.4559 | 0.6126 | 0.082* | |
H6B | 0.5651 | 0.4362 | 0.6448 | 0.082* | |
H6C | 0.5559 | 0.4546 | 0.5549 | 0.082* | |
O3 | 1.11496 (9) | 0.27235 (5) | 0.61885 (6) | 0.0177 (2) | |
C31 | 1.20406 (14) | 0.31106 (8) | 0.67276 (9) | 0.0188 (3) | |
C32 | 1.21043 (16) | 0.38543 (9) | 0.66742 (10) | 0.0254 (3) | |
C33 | 1.30984 (18) | 0.41875 (10) | 0.71862 (11) | 0.0321 (4) | |
H33 | 1.3176 | 0.4695 | 0.7171 | 0.039* | |
C34 | 1.39626 (18) | 0.38061 (11) | 0.77075 (11) | 0.0345 (4) | |
H34 | 1.4627 | 0.4049 | 0.8043 | 0.041* | |
C35 | 1.38648 (16) | 0.30669 (11) | 0.77430 (10) | 0.0323 (4) | |
H35 | 1.4462 | 0.2801 | 0.8103 | 0.039* | |
C36 | 1.28938 (15) | 0.27160 (9) | 0.72526 (9) | 0.0239 (3) | |
H36 | 1.2815 | 0.2209 | 0.7277 | 0.029* | |
C7 | 1.12060 (19) | 0.42982 (9) | 0.60906 (12) | 0.0348 (4) | |
H7 | 1.0525 | 0.3972 | 0.5818 | 0.042* | |
C8 | 1.1902 (2) | 0.46085 (12) | 0.54837 (13) | 0.0469 (5) | |
H8A | 1.2633 | 0.4889 | 0.5743 | 0.07* | |
H8B | 1.1327 | 0.492 | 0.5129 | 0.07* | |
H8C | 1.2193 | 0.4216 | 0.519 | 0.07* | |
C9 | 1.0576 (2) | 0.48884 (11) | 0.64923 (15) | 0.0489 (5) | |
H9A | 1.0076 | 0.4669 | 0.6842 | 0.073* | |
H9B | 1.002 | 0.5176 | 0.6101 | 0.073* | |
H9C | 1.123 | 0.5198 | 0.6791 | 0.073* | |
C41 | 0.83491 (16) | 0.02524 (9) | 0.55413 (12) | 0.0333 (4) | |
H41 | 0.8628 | −0.0216 | 0.5708 | 0.04* | |
C42 | 0.84169 (15) | 0.04785 (10) | 0.48025 (11) | 0.0317 (4) | |
H42 | 0.8748 | 0.0169 | 0.446 | 0.038* | |
C43 | 0.79892 (16) | 0.11759 (11) | 0.45596 (10) | 0.0311 (4) | |
H43 | 0.8092 | 0.1348 | 0.4067 | 0.037* | |
C44 | 0.74158 (15) | 0.16136 (9) | 0.50399 (12) | 0.0325 (4) | |
H44 | 0.7054 | 0.2061 | 0.4856 | 0.039* | |
C45 | 0.73806 (15) | 0.13846 (10) | 0.57974 (12) | 0.0336 (4) | |
H45 | 0.7026 | 0.1686 | 0.6136 | 0.04* | |
C46 | 0.78659 (17) | 0.07160 (10) | 0.60504 (11) | 0.0336 (4) | |
H46 | 0.7873 | 0.057 | 0.6569 | 0.04* | |
C | 0.3830 (2) | 0.11900 (17) | 0.61087 (14) | 0.0572 (7) | |
H0A | 0.3078 | 0.0935 | 0.6222 | 0.069* | |
H0B | 0.3565 | 0.1681 | 0.5932 | 0.069* | |
Cl3 | 0.43873 (5) | 0.07392 (5) | 0.53697 (4) | 0.0675 (2) | |
Cl4 | 0.49854 (5) | 0.12445 (4) | 0.69600 (3) | 0.05209 (15) | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
Ru | 0.01353 (6) | 0.01347 (6) | 0.01503 (6) | −0.00173 (4) | 0.00364 (4) | −0.00194 (4) |
P | 0.01402 (16) | 0.01393 (16) | 0.01270 (16) | −0.00022 (12) | 0.00244 (12) | −0.00133 (12) |
Cl1 | 0.02048 (16) | 0.02381 (17) | 0.01954 (17) | −0.00274 (13) | 0.00902 (13) | −0.00287 (13) |
Cl2 | 0.02145 (16) | 0.02124 (17) | 0.02025 (17) | 0.00425 (13) | 0.00304 (13) | 0.00159 (13) |
O1 | 0.0165 (5) | 0.0220 (5) | 0.0128 (5) | 0.0012 (4) | 0.0033 (4) | −0.0022 (4) |
C11 | 0.0165 (6) | 0.0321 (8) | 0.0120 (6) | 0.0022 (6) | 0.0029 (5) | 0.0003 (6) |
C12 | 0.0202 (7) | 0.0398 (9) | 0.0156 (7) | 0.0069 (6) | 0.0016 (6) | −0.0043 (6) |
C13 | 0.0285 (9) | 0.0624 (13) | 0.0244 (9) | 0.0114 (9) | 0.0113 (7) | −0.0038 (9) |
C14 | 0.0307 (9) | 0.0761 (16) | 0.0275 (9) | 0.0008 (10) | 0.0156 (8) | 0.0089 (10) |
C15 | 0.0313 (9) | 0.0505 (12) | 0.0276 (9) | −0.0070 (8) | 0.0065 (7) | 0.0115 (8) |
C16 | 0.0237 (8) | 0.0334 (9) | 0.0188 (7) | −0.0003 (6) | 0.0034 (6) | 0.0032 (6) |
C1 | 0.0318 (9) | 0.0328 (9) | 0.0226 (8) | 0.0104 (7) | 0.0017 (7) | −0.0103 (7) |
C2 | 0.0380 (10) | 0.0422 (11) | 0.0346 (10) | 0.0044 (8) | −0.0032 (8) | −0.0170 (8) |
C3 | 0.0517 (13) | 0.0484 (12) | 0.0410 (11) | 0.0246 (10) | 0.0060 (9) | −0.0148 (10) |
O2 | 0.0214 (5) | 0.0181 (5) | 0.0146 (5) | 0.0051 (4) | 0.0013 (4) | −0.0006 (4) |
C21 | 0.0216 (7) | 0.0148 (6) | 0.0164 (7) | −0.0004 (5) | −0.0004 (5) | 0.0003 (5) |
C22 | 0.0222 (7) | 0.0239 (7) | 0.0230 (8) | 0.0035 (6) | 0.0013 (6) | 0.0017 (6) |
C23 | 0.0255 (8) | 0.0342 (9) | 0.0278 (9) | 0.0051 (7) | −0.0019 (7) | 0.0050 (7) |
C24 | 0.0365 (9) | 0.0318 (9) | 0.0194 (8) | 0.0004 (7) | −0.0030 (7) | 0.0041 (7) |
C25 | 0.0364 (9) | 0.0240 (8) | 0.0182 (7) | −0.0020 (7) | 0.0053 (6) | 0.0005 (6) |
C26 | 0.0233 (7) | 0.0184 (7) | 0.0205 (7) | −0.0014 (6) | 0.0034 (6) | −0.0003 (6) |
C4 | 0.0250 (8) | 0.0435 (10) | 0.0270 (9) | 0.0124 (7) | 0.0062 (7) | 0.0064 (7) |
C5 | 0.0382 (11) | 0.0728 (17) | 0.0582 (15) | −0.0049 (11) | 0.0234 (11) | −0.0021 (13) |
C6 | 0.0721 (16) | 0.0494 (13) | 0.0493 (13) | 0.0107 (12) | 0.0278 (12) | −0.0086 (11) |
O3 | 0.0182 (5) | 0.0185 (5) | 0.0166 (5) | −0.0056 (4) | 0.0036 (4) | −0.0038 (4) |
C31 | 0.0172 (6) | 0.0213 (7) | 0.0182 (7) | −0.0053 (5) | 0.0042 (5) | −0.0052 (6) |
C32 | 0.0276 (8) | 0.0210 (7) | 0.0275 (8) | −0.0048 (6) | 0.0051 (6) | −0.0044 (6) |
C33 | 0.0368 (9) | 0.0264 (8) | 0.0332 (9) | −0.0132 (7) | 0.0068 (8) | −0.0087 (7) |
C34 | 0.0308 (9) | 0.0455 (11) | 0.0261 (9) | −0.0180 (8) | 0.0027 (7) | −0.0088 (8) |
C35 | 0.0247 (8) | 0.0447 (10) | 0.0250 (9) | −0.0062 (7) | −0.0017 (7) | 0.0029 (8) |
C36 | 0.0216 (7) | 0.0260 (8) | 0.0241 (8) | −0.0019 (6) | 0.0043 (6) | 0.0011 (6) |
C7 | 0.0385 (10) | 0.0197 (8) | 0.0422 (11) | −0.0034 (7) | −0.0021 (8) | 0.0022 (7) |
C8 | 0.0638 (14) | 0.0379 (11) | 0.0374 (11) | 0.0002 (10) | 0.0056 (10) | 0.0064 (9) |
C9 | 0.0524 (13) | 0.0309 (10) | 0.0657 (15) | 0.0081 (9) | 0.0174 (11) | 0.0096 (10) |
C41 | 0.0249 (8) | 0.0188 (8) | 0.0526 (12) | −0.0090 (6) | −0.0020 (8) | 0.0011 (7) |
C42 | 0.0193 (7) | 0.0348 (9) | 0.0407 (10) | −0.0080 (7) | 0.0052 (7) | −0.0241 (8) |
C43 | 0.0227 (8) | 0.0460 (10) | 0.0216 (8) | −0.0137 (7) | −0.0034 (6) | −0.0003 (7) |
C44 | 0.0166 (7) | 0.0216 (8) | 0.0538 (12) | −0.0028 (6) | −0.0069 (7) | −0.0024 (8) |
C45 | 0.0158 (7) | 0.0386 (10) | 0.0490 (11) | −0.0094 (7) | 0.0125 (7) | −0.0229 (8) |
C46 | 0.0322 (9) | 0.0414 (10) | 0.0283 (9) | −0.0218 (8) | 0.0085 (7) | −0.0005 (8) |
C | 0.0263 (10) | 0.101 (2) | 0.0446 (13) | 0.0016 (11) | 0.0074 (9) | −0.0114 (13) |
Cl3 | 0.0337 (3) | 0.1178 (6) | 0.0528 (3) | −0.0203 (3) | 0.0128 (2) | −0.0360 (4) |
Cl4 | 0.0398 (3) | 0.0828 (4) | 0.0343 (3) | 0.0159 (3) | 0.0085 (2) | −0.0005 (3) |
Geometric parameters (Å, º) top
Ru—P | 2.2790 (4) | C5—H5B | 0.98 |
Ru—Cl1 | 2.4052 (4) | C5—H5C | 0.98 |
Ru—Cl2 | 2.4046 (4) | C6—H6A | 0.98 |
P—O1 | 1.5942 (10) | C6—H6B | 0.98 |
P—O3 | 1.5837 (10) | C6—H6C | 0.98 |
P—O2 | 1.6167 (10) | O3—C31 | 1.4101 (17) |
O1—C11 | 1.4095 (17) | C31—C36 | 1.382 (2) |
C11—C16 | 1.379 (2) | C31—C32 | 1.390 (2) |
C11—C12 | 1.399 (2) | C32—C33 | 1.404 (2) |
C12—C13 | 1.397 (2) | C32—C7 | 1.513 (2) |
C12—C1 | 1.511 (3) | C33—C34 | 1.372 (3) |
C13—C14 | 1.380 (3) | C33—H33 | 0.95 |
C13—H13 | 0.95 | C34—C35 | 1.382 (3) |
C14—C15 | 1.383 (3) | C34—H34 | 0.95 |
C14—H14 | 0.95 | C35—C36 | 1.384 (2) |
C15—C16 | 1.393 (2) | C35—H35 | 0.95 |
C15—H15 | 0.95 | C36—H36 | 0.95 |
C16—H16 | 0.95 | C7—C8 | 1.529 (3) |
C1—C3 | 1.528 (2) | C7—C9 | 1.532 (3) |
C1—C2 | 1.532 (3) | C7—H7 | 1 |
C1—H1 | 1 | C8—H8A | 0.98 |
C2—H2A | 0.98 | C8—H8B | 0.98 |
C2—H2B | 0.98 | C8—H8C | 0.98 |
C2—H2C | 0.98 | C9—H9A | 0.98 |
C3—H3A | 0.98 | C9—H9B | 0.98 |
C3—H3B | 0.98 | C9—H9C | 0.98 |
C3—H3C | 0.98 | C41—C42 | 1.380 (3) |
O2—C21 | 1.4028 (17) | C41—C46 | 1.412 (3) |
C21—C26 | 1.386 (2) | C41—H41 | 0.95 |
C21—C22 | 1.396 (2) | C42—C43 | 1.416 (3) |
C22—C23 | 1.399 (2) | C42—H42 | 0.95 |
C22—C4 | 1.517 (2) | C43—C44 | 1.399 (3) |
C23—C24 | 1.383 (3) | C43—H43 | 0.95 |
C23—H23 | 0.95 | C44—C45 | 1.405 (3) |
C24—C25 | 1.382 (3) | C44—H44 | 0.95 |
C24—H24 | 0.95 | C45—C46 | 1.389 (3) |
C25—C26 | 1.388 (2) | C45—H45 | 0.95 |
C25—H25 | 0.95 | C46—H46 | 0.95 |
C26—H26 | 0.95 | C—Cl3 | 1.746 (2) |
C4—C6 | 1.519 (3) | C—Cl4 | 1.755 (2) |
C4—C5 | 1.529 (3) | C—H0A | 0.99 |
C4—H4 | 1 | C—H0B | 0.99 |
C5—H5A | 0.98 | | |
| | | |
P—Ru—Cl2 | 84.400 (13) | C4—C5—H5B | 109.5 |
P—Ru—Cl1 | 89.504 (13) | H5A—C5—H5B | 109.5 |
Cl2—Ru—Cl1 | 88.787 (14) | C4—C5—H5C | 109.5 |
O3—P—O1 | 99.52 (5) | H5A—C5—H5C | 109.5 |
O3—P—O2 | 105.19 (6) | H5B—C5—H5C | 109.5 |
O1—P—O2 | 98.11 (5) | C4—C6—H6A | 109.5 |
O3—P—Ru | 114.60 (4) | C4—C6—H6B | 109.5 |
O1—P—Ru | 120.05 (4) | H6A—C6—H6B | 109.5 |
O2—P—Ru | 116.60 (4) | C4—C6—H6C | 109.5 |
C11—O1—P | 126.71 (9) | H6A—C6—H6C | 109.5 |
C16—C11—C12 | 123.08 (15) | H6B—C6—H6C | 109.5 |
C16—C11—O1 | 119.03 (14) | C31—O3—P | 129.67 (9) |
C12—C11—O1 | 117.61 (14) | C36—C31—C32 | 122.65 (14) |
C13—C12—C11 | 115.99 (17) | C36—C31—O3 | 117.15 (13) |
C13—C12—C1 | 123.35 (16) | C32—C31—O3 | 119.97 (14) |
C11—C12—C1 | 120.52 (14) | C31—C32—C33 | 115.98 (16) |
C14—C13—C12 | 121.94 (18) | C31—C32—C7 | 123.80 (15) |
C14—C13—H13 | 119 | C33—C32—C7 | 120.18 (15) |
C12—C13—H13 | 119 | C34—C33—C32 | 122.38 (17) |
C13—C14—C15 | 120.48 (17) | C34—C33—H33 | 118.8 |
C13—C14—H14 | 119.8 | C32—C33—H33 | 118.8 |
C15—C14—H14 | 119.8 | C33—C34—C35 | 119.84 (16) |
C14—C15—C16 | 119.35 (19) | C33—C34—H34 | 120.1 |
C14—C15—H15 | 120.3 | C35—C34—H34 | 120.1 |
C16—C15—H15 | 120.3 | C34—C35—C36 | 119.77 (17) |
C11—C16—C15 | 119.11 (17) | C34—C35—H35 | 120.1 |
C11—C16—H16 | 120.4 | C36—C35—H35 | 120.1 |
C15—C16—H16 | 120.4 | C31—C36—C35 | 119.37 (16) |
C12—C1—C3 | 113.85 (17) | C31—C36—H36 | 120.3 |
C12—C1—C2 | 109.66 (15) | C35—C36—H36 | 120.3 |
C3—C1—C2 | 109.58 (15) | C32—C7—C8 | 110.16 (17) |
C12—C1—H1 | 107.8 | C32—C7—C9 | 111.14 (17) |
C3—C1—H1 | 107.8 | C8—C7—C9 | 111.67 (16) |
C2—C1—H1 | 107.8 | C32—C7—H7 | 107.9 |
C1—C2—H2A | 109.5 | C8—C7—H7 | 107.9 |
C1—C2—H2B | 109.5 | C9—C7—H7 | 107.9 |
H2A—C2—H2B | 109.5 | C7—C8—H8A | 109.5 |
C1—C2—H2C | 109.5 | C7—C8—H8B | 109.5 |
H2A—C2—H2C | 109.5 | H8A—C8—H8B | 109.5 |
H2B—C2—H2C | 109.5 | C7—C8—H8C | 109.5 |
C1—C3—H3A | 109.5 | H8A—C8—H8C | 109.5 |
C1—C3—H3B | 109.5 | H8B—C8—H8C | 109.5 |
H3A—C3—H3B | 109.5 | C7—C9—H9A | 109.5 |
C1—C3—H3C | 109.5 | C7—C9—H9B | 109.5 |
H3A—C3—H3C | 109.5 | H9A—C9—H9B | 109.5 |
H3B—C3—H3C | 109.5 | C7—C9—H9C | 109.5 |
C21—O2—P | 124.19 (9) | H9A—C9—H9C | 109.5 |
C26—C21—C22 | 122.61 (14) | H9B—C9—H9C | 109.5 |
C26—C21—O2 | 120.46 (13) | C42—C41—C46 | 120.13 (17) |
C22—C21—O2 | 116.94 (13) | C42—C41—H41 | 119.9 |
C21—C22—C23 | 116.39 (15) | C46—C41—H41 | 119.9 |
C21—C22—C4 | 122.66 (14) | C41—C42—C43 | 119.39 (16) |
C23—C22—C4 | 120.94 (15) | C41—C42—H42 | 120.3 |
C24—C23—C22 | 122.01 (16) | C43—C42—H42 | 120.3 |
C24—C23—H23 | 119 | C44—C43—C42 | 120.51 (17) |
C22—C23—H23 | 119 | C44—C43—H43 | 119.7 |
C25—C24—C23 | 119.82 (16) | C42—C43—H43 | 119.7 |
C25—C24—H24 | 120.1 | C43—C44—C45 | 119.33 (16) |
C23—C24—H24 | 120.1 | C43—C44—H44 | 120.3 |
C24—C25—C26 | 120.12 (16) | C45—C44—H44 | 120.3 |
C24—C25—H25 | 119.9 | C46—C45—C44 | 119.90 (16) |
C26—C25—H25 | 119.9 | C46—C45—H45 | 120.1 |
C21—C26—C25 | 118.99 (15) | C44—C45—H45 | 120.1 |
C21—C26—H26 | 120.5 | C45—C46—C41 | 120.40 (17) |
C25—C26—H26 | 120.5 | C45—C46—H46 | 119.8 |
C22—C4—C6 | 110.22 (16) | C41—C46—H46 | 119.8 |
C22—C4—C5 | 112.07 (17) | Cl3—C—Cl4 | 111.97 (13) |
C6—C4—C5 | 110.91 (18) | Cl3—C—H0A | 109.2 |
C22—C4—H4 | 107.8 | Cl4—C—H0A | 109.2 |
C6—C4—H4 | 107.8 | Cl3—C—H0B | 109.2 |
C5—C4—H4 | 107.8 | Cl4—C—H0B | 109.2 |
C4—C5—H5A | 109.5 | H0A—C—H0B | 107.9 |
| | | |
Cl2—Ru—P—O3 | 71.81 (5) | C4—C22—C23—C24 | 178.66 (17) |
Cl1—Ru—P—O3 | −17.02 (5) | C22—C23—C24—C25 | −1.3 (3) |
Cl2—Ru—P—O1 | −46.54 (5) | C23—C24—C25—C26 | 2.4 (3) |
Cl1—Ru—P—O1 | −135.37 (5) | C22—C21—C26—C25 | −1.4 (2) |
Cl2—Ru—P—O2 | −164.71 (5) | O2—C21—C26—C25 | 178.18 (13) |
Cl1—Ru—P—O2 | 106.46 (5) | C24—C25—C26—C21 | −1.1 (2) |
O3—P—O1—C11 | 174.06 (12) | C21—C22—C4—C6 | 107.4 (2) |
O2—P—O1—C11 | 67.07 (12) | C23—C22—C4—C6 | −72.3 (2) |
Ru—P—O1—C11 | −60.16 (13) | C21—C22—C4—C5 | −128.61 (19) |
P—O1—C11—C16 | 78.90 (17) | C23—C22—C4—C5 | 51.7 (2) |
P—O1—C11—C12 | −107.07 (14) | O1—P—O3—C31 | −14.94 (13) |
C16—C11—C12—C13 | −2.2 (2) | O2—P—O3—C31 | 86.24 (13) |
O1—C11—C12—C13 | −175.99 (14) | Ru—P—O3—C31 | −144.37 (11) |
C16—C11—C12—C1 | 173.58 (15) | P—O3—C31—C36 | 83.91 (16) |
O1—C11—C12—C1 | −0.2 (2) | P—O3—C31—C32 | −101.50 (16) |
C11—C12—C13—C14 | 0.6 (3) | C36—C31—C32—C33 | 0.3 (2) |
C1—C12—C13—C14 | −175.11 (17) | O3—C31—C32—C33 | −173.97 (14) |
C12—C13—C14—C15 | 0.6 (3) | C36—C31—C32—C7 | 178.24 (16) |
C13—C14—C15—C16 | −0.3 (3) | O3—C31—C32—C7 | 4.0 (2) |
C12—C11—C16—C15 | 2.6 (2) | C31—C32—C33—C34 | 0.3 (3) |
O1—C11—C16—C15 | 176.32 (14) | C7—C32—C33—C34 | −177.74 (18) |
C14—C15—C16—C11 | −1.3 (3) | C32—C33—C34—C35 | −0.4 (3) |
C13—C12—C1—C3 | −21.6 (2) | C33—C34—C35—C36 | −0.1 (3) |
C11—C12—C1—C3 | 162.90 (16) | C32—C31—C36—C35 | −0.8 (2) |
C13—C12—C1—C2 | 101.54 (19) | O3—C31—C36—C35 | 173.67 (14) |
C11—C12—C1—C2 | −73.93 (19) | C34—C35—C36—C31 | 0.6 (3) |
O3—P—O2—C21 | 82.13 (12) | C31—C32—C7—C8 | −110.15 (19) |
O1—P—O2—C21 | −175.64 (11) | C33—C32—C7—C8 | 67.7 (2) |
Ru—P—O2—C21 | −46.06 (12) | C31—C32—C7—C9 | 125.54 (19) |
P—O2—C21—C26 | −35.88 (18) | C33—C32—C7—C9 | −56.6 (2) |
P—O2—C21—C22 | 143.75 (12) | C46—C41—C42—C43 | −0.5 (2) |
C26—C21—C22—C23 | 2.4 (2) | C41—C42—C43—C44 | −4.8 (2) |
O2—C21—C22—C23 | −177.18 (14) | C42—C43—C44—C45 | 6.3 (2) |
C26—C21—C22—C4 | −177.27 (16) | C43—C44—C45—C46 | −2.7 (2) |
O2—C21—C22—C4 | 3.1 (2) | C44—C45—C46—C41 | −2.5 (2) |
C21—C22—C23—C24 | −1.0 (3) | C42—C41—C46—C45 | 4.1 (2) |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
C1—H1···O2 | 1 | 2.44 | 3.308 (2) | 145 |
C2—H2C···O1 | 0.98 | 2.57 | 3.149 (2) | 118 |
C4—H4···O2 | 1 | 2.36 | 2.851 (2) | 109 |
C7—H7···O3 | 1 | 2.47 | 2.938 (2) | 108 |
C16—H16···Cl2 | 0.95 | 2.76 | 3.5885 (17) | 146 |
C41—H41···Cl1i | 0.95 | 2.8 | 3.5863 (19) | 141 |
C42—H42···Cl2i | 0.95 | 2.76 | 3.6875 (17) | 164 |
C—H0A···Cl2ii | 0.99 | 2.52 | 3.442 (2) | 155 |
Symmetry codes: (i) −x+2, −y, −z+1; (ii) x−1, y, z. |
Comparative geometrical parameters for selected [(η6-C6H6)RuCl2(L)]
(L = ligand) complexes. topL | Ru-L (Å) | Ru-Cl1 (Å) | Ru-Cl2 (Å) | notes |
P(2-iPr-C6H4)3 | 2.2790 (4) | 2.4052 (4) | 2.4046 (4) | TW |
Me2HPz | 2.122 (7) | 2.423 (1) | 2.410 (2) | (i) |
Me2HPz | 2.125 (7) | 2.417 (2) | 2.412 (2) | (i) |
PPh3 | 2.364 (1) | 2.412 (1) | 2.406 (2) | (ii) |
pta | 2.237 (4) | 2.4155 (18) | s | (iii) |
PPh2MeIm | 2.3529 (10) | 2.4085 (11) | 2.4055 (10) | (iv) |
PPh2MeIm+ | 2.3404 (14) | 2.4221 (15) | 2.398 (13) | (iv) |
Notes: TW = this work; Pz = pyrazole; pta = 1,3,5-triaza-7-phophaadamantane;
s = generated by symmetry; MeIm = 1-methylimidazol-2-yl; MeIm+ =
1-methylimidazol-3-ium-2-yl. (i) Małecki et al. (2004). (ii)
Elsegood &
Tochner (1995). (iii) Horváth or Hórvath et al.
(2004). (iv) Caballero et
al. (2004). |