metal-organic compounds
(η6-Benzene)dichlorido(dicyclohexylphenylphosphane)ruthenium(II) benzene sesquisolvate
aResearch Centre for Synthesis and Catalysis, Department of Chemistry, University of Johannesburg (APK Campus), PO Box 524, Auckland Park, Johannesburg, 2006, South Africa
*Correspondence e-mail: daviswl24@yahoo.com
The 2(C6H6)(C18H27P)]·1.5C6H6, contains one molecule of the RuII complex and one and a half solvent molecules as one of these is located about a centre of inversion. The RuII atom has a classical three-legged piano-stool environment being coordinated by an η6-benzene ligand [Ru—centroid = 1.6964 (6) Å], two chloride ligands with an average Ru—Cl bond length of 2.4138 (3) Å and a dicyclohexylphenylphosphane ligand [Ru—P = 2.3786 (3) Å]. The effective cone angle for the phosphane was calculated to be 158°. In the crystal, weak C—H⋯Cl hydrogen bonds link the RuII complexes into centrosymmetric dimers. The crystal packing exhibits intra- and intermolecular C—H⋯π interactions resulting in a zigzag pattern in the [101] direction.
of the title compound, [RuClRelated literature
For background to the II–arene complexes, see: Chen et al. (2002); Crochet et al. (2003); Aydemir et al. (2011); Wang et al. (2011). For ring-opening metathesis polymerization with Ru–arene complexes, see: Stumpf et al. (1995). For background to cone angles, see: Tolman (1977); Otto (2001). For a description of the Cambridge Structural Database, see: Allen (2002).
of RuExperimental
Crystal data
|
Refinement
|
Data collection: APEX2 (Bruker, 2011); cell SAINT (Bruker, 2008); data reduction: SAINT and XPREP (Bruker, 2008); program(s) used to solve structure: SIR97 (Altomare et al., 1999); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: DIAMOND (Brandenburg & Putz, 2005); software used to prepare material for publication: publCIF (Westrip, 2010) and WinGX (Farrugia, 1999).
Supporting information
10.1107/S1600536812044674/cv5349sup1.cif
contains datablocks global, I. DOI:Structure factors: contains datablock I. DOI: 10.1107/S1600536812044674/cv5349Isup2.hkl
[(C6H6)RuCl2]2 (50.0 mg, 0.10 mmol) and dicyclohexylphenylphosphane (60.2 mg, 0.22 mmol) in benzene (25 ml) were refluxed under argon for 4 h. The resulting red solution was cooled and filtered to obtain the title complex as orange needles suitable for a single-crystal X-ray study. Analytical data: 31P {H} NMR (CDCl3, 161.99 MHz): δ (p.p.m.) 24.74 (s, 1P). 1H NMR (CDCl3, 400 MHz): δ (p.p.m.) 1.23 - 2.45 (m, 22H, 2×C6H11); 5.27 (s, 6H, C6H6); 7.43 (m, 3H, Ar—H of C6H5); 7.77 (t, 2H, Ar—H of C6H5); 7.34 (s, 6H, Ar—H of C6H6 co-crystallized solvate)
The aromatic, methine and methylene H atoms were placed in geometrically idealized positions (C—H = 0.95–1.00) and allowed to ride on their parent atoms, with Uiso(H) = 1.2Ueq(C).
Data collection: APEX2 (Bruker, 2011); cell
SAINT (Bruker, 2008); data reduction: SAINT and XPREP (Bruker, 2008); program(s) used to solve structure: SIR97 (Altomare et al., 1999); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: DIAMOND (Brandenburg & Putz, 2005); software used to prepare material for publication: publCIF (Westrip, 2010) and WinGX (Farrugia, 1999).Fig. 1. A view of the title complex, showing the atom-numbering scheme and 50% probability displacement ellipsoids. Accented lettering indicate atoms generated by symmetry code: 1 - x,1 - y,1 - z. | |
Fig. 2. Packing diagram showing the C—H···Cl/π interactions (indicated by red dashed lines). |
[RuCl2(C6H6)(C18H27P)]·1.5C6H6 | Z = 2 |
Mr = 641.61 | F(000) = 666 |
Triclinic, P1 | Dx = 1.407 Mg m−3 |
Hall symbol: -P 1 | Mo Kα radiation, λ = 0.71073 Å |
a = 10.0893 (8) Å | Cell parameters from 9969 reflections |
b = 10.8325 (9) Å | θ = 2.4–28.4° |
c = 14.4937 (12) Å | µ = 0.77 mm−1 |
α = 90.346 (2)° | T = 100 K |
β = 91.748 (1)° | Needle, orange |
γ = 106.979 (1)° | 0.43 × 0.17 × 0.16 mm |
V = 1514.1 (2) Å3 |
Bruker APEX DUO 4K CCD diffractometer | 7589 independent reflections |
Radiation source: sealed tube | 7093 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.022 |
Detector resolution: 8.4 pixels mm-1 | θmax = 28.4°, θmin = 2.0° |
ϕ and ω scans | h = −12→13 |
Absorption correction: multi-scan (SADABS; Bruker, 2008) | k = −14→14 |
Tmin = 0.734, Tmax = 0.887 | l = −19→19 |
49345 measured reflections |
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)] = 0.018 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.048 | H-atom parameters constrained |
S = 1.03 | w = 1/[σ2(Fo2) + (0.0236P)2 + 0.8124P] where P = (Fo2 + 2Fc2)/3 |
7589 reflections | (Δ/σ)max = 0.006 |
334 parameters | Δρmax = 0.54 e Å−3 |
0 restraints | Δρmin = −0.43 e Å−3 |
[RuCl2(C6H6)(C18H27P)]·1.5C6H6 | γ = 106.979 (1)° |
Mr = 641.61 | V = 1514.1 (2) Å3 |
Triclinic, P1 | Z = 2 |
a = 10.0893 (8) Å | Mo Kα radiation |
b = 10.8325 (9) Å | µ = 0.77 mm−1 |
c = 14.4937 (12) Å | T = 100 K |
α = 90.346 (2)° | 0.43 × 0.17 × 0.16 mm |
β = 91.748 (1)° |
Bruker APEX DUO 4K CCD diffractometer | 7589 independent reflections |
Absorption correction: multi-scan (SADABS; Bruker, 2008) | 7093 reflections with I > 2σ(I) |
Tmin = 0.734, Tmax = 0.887 | Rint = 0.022 |
49345 measured reflections |
R[F2 > 2σ(F2)] = 0.018 | 0 restraints |
wR(F2) = 0.048 | H-atom parameters constrained |
S = 1.03 | Δρmax = 0.54 e Å−3 |
7589 reflections | Δρmin = −0.43 e Å−3 |
334 parameters |
Experimental. The intensity data was collected on a Bruker Apex DUO 4 K CCD diffractometer using an exposure time of 10 s/frame. A total of 3975 frames were collected with a frame width of 0.5° covering up to θ = 28.39° with 99.8% 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. |
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 | ||
C13 | 0.23801 (12) | 0.90129 (11) | 0.13276 (8) | 0.0128 (2) | |
H13 | 0.2204 | 0.8214 | 0.1704 | 0.015* | |
Ru1 | 0.291263 (9) | 1.021309 (9) | 0.364239 (6) | 0.01185 (3) | |
Cl2 | 0.35692 (3) | 0.82818 (3) | 0.330250 (19) | 0.01576 (6) | |
Cl1 | 0.51362 (3) | 1.14613 (3) | 0.310072 (19) | 0.01539 (6) | |
P1 | 0.20357 (3) | 1.02428 (3) | 0.210321 (19) | 0.01140 (6) | |
C21 | −0.20563 (14) | 1.02643 (15) | 0.22475 (9) | 0.0240 (3) | |
H21 | −0.2563 | 1.0878 | 0.2254 | 0.029* | |
C24 | −0.05677 (13) | 0.84778 (13) | 0.22298 (9) | 0.0199 (2) | |
H24 | −0.0066 | 0.786 | 0.2228 | 0.024* | |
C7 | 0.27287 (12) | 1.18293 (11) | 0.15452 (8) | 0.0141 (2) | |
H7 | 0.3714 | 1.1894 | 0.1416 | 0.017* | |
C3 | 0.34809 (14) | 1.10795 (13) | 0.50804 (8) | 0.0205 (2) | |
H3 | 0.4342 | 1.1512 | 0.5383 | 0.025* | |
C19 | 0.01393 (12) | 0.97891 (12) | 0.21045 (8) | 0.0151 (2) | |
C12 | 0.28055 (14) | 1.29985 (12) | 0.21791 (8) | 0.0189 (2) | |
H12A | 0.1856 | 1.3019 | 0.2314 | 0.023* | |
H12B | 0.3285 | 1.2914 | 0.2771 | 0.023* | |
C15 | 0.17462 (13) | 0.74268 (12) | −0.00063 (8) | 0.0184 (2) | |
H15A | 0.1478 | 0.6683 | 0.0413 | 0.022* | |
H15B | 0.1177 | 0.7191 | −0.0585 | 0.022* | |
C6 | 0.08641 (13) | 0.98146 (14) | 0.42244 (8) | 0.0207 (3) | |
H6 | −0.0029 | 0.9389 | 0.3963 | 0.025* | |
C5 | 0.16284 (14) | 0.91076 (14) | 0.47028 (9) | 0.0217 (3) | |
H5 | 0.1282 | 0.8193 | 0.472 | 0.026* | |
C9 | 0.28183 (16) | 1.32479 (12) | 0.01475 (9) | 0.0227 (3) | |
H9A | 0.3764 | 1.3232 | −0.0004 | 0.027* | |
H9B | 0.2323 | 1.334 | −0.0436 | 0.027* | |
C23 | −0.19916 (14) | 0.80717 (14) | 0.23563 (10) | 0.0247 (3) | |
H23 | −0.2455 | 0.7181 | 0.2432 | 0.03* | |
C2 | 0.27617 (14) | 1.18010 (13) | 0.45379 (8) | 0.0197 (2) | |
H2 | 0.3173 | 1.2698 | 0.4449 | 0.024* | |
C1 | 0.14425 (13) | 1.11748 (13) | 0.41362 (8) | 0.0199 (2) | |
H1 | 0.094 | 1.1659 | 0.3807 | 0.024* | |
C20 | −0.06275 (13) | 1.06759 (13) | 0.21126 (8) | 0.0188 (2) | |
H20 | −0.0174 | 1.1566 | 0.2026 | 0.023* | |
C22 | −0.27381 (14) | 0.89684 (15) | 0.23717 (9) | 0.0255 (3) | |
H22 | −0.3707 | 0.8694 | 0.2467 | 0.031* | |
C4 | 0.29264 (14) | 0.97544 (14) | 0.51658 (8) | 0.0216 (3) | |
H4 | 0.3402 | 0.9279 | 0.5528 | 0.026* | |
C17 | 0.42054 (13) | 0.81708 (12) | 0.06445 (8) | 0.0166 (2) | |
H17A | 0.5191 | 0.8397 | 0.0478 | 0.02* | |
H17B | 0.4037 | 0.7463 | 0.1095 | 0.02* | |
C8 | 0.20528 (14) | 1.19726 (12) | 0.05982 (8) | 0.0187 (2) | |
H8A | 0.2067 | 1.1243 | 0.0188 | 0.022* | |
H8B | 0.1073 | 1.1941 | 0.0679 | 0.022* | |
C29 | 0.13687 (16) | 0.64750 (15) | 0.65832 (10) | 0.0294 (3) | |
H29 | 0.2034 | 0.7136 | 0.6276 | 0.035* | |
C25 | −0.08721 (15) | 0.49053 (14) | 0.65995 (11) | 0.0298 (3) | |
H25 | −0.174 | 0.4484 | 0.6301 | 0.036* | |
C10 | 0.29188 (18) | 1.44049 (13) | 0.07790 (10) | 0.0281 (3) | |
H10A | 0.1979 | 1.4486 | 0.0869 | 0.034* | |
H10B | 0.3476 | 1.5203 | 0.0485 | 0.034* | |
C30 | 0.00960 (16) | 0.58659 (15) | 0.61498 (10) | 0.0297 (3) | |
H30 | −0.0109 | 0.6108 | 0.5546 | 0.036* | |
C11 | 0.35888 (16) | 1.42569 (12) | 0.17166 (10) | 0.0257 (3) | |
H11A | 0.3598 | 1.4998 | 0.2123 | 0.031* | |
H11B | 0.4562 | 1.4266 | 0.1632 | 0.031* | |
C27 | 0.06923 (17) | 0.51601 (14) | 0.79164 (10) | 0.0281 (3) | |
H27 | 0.0895 | 0.4918 | 0.8521 | 0.034* | |
C28 | 0.16672 (16) | 0.61169 (14) | 0.74646 (10) | 0.0288 (3) | |
H28 | 0.2541 | 0.6528 | 0.7759 | 0.035* | |
C26 | −0.05788 (16) | 0.45575 (13) | 0.74830 (11) | 0.0284 (3) | |
H26 | −0.125 | 0.3905 | 0.7793 | 0.034* | |
C18 | 0.39160 (12) | 0.93493 (11) | 0.10898 (8) | 0.0143 (2) | |
H18A | 0.4145 | 1.008 | 0.0658 | 0.017* | |
H18B | 0.4504 | 0.9612 | 0.1658 | 0.017* | |
C14 | 0.14528 (13) | 0.86015 (12) | 0.04474 (8) | 0.0176 (2) | |
H14A | 0.0465 | 0.838 | 0.0607 | 0.021* | |
H14B | 0.1641 | 0.9325 | 0.0009 | 0.021* | |
C16 | 0.32791 (13) | 0.77092 (12) | −0.02223 (8) | 0.0180 (2) | |
H16A | 0.3521 | 0.8381 | −0.0699 | 0.022* | |
H16B | 0.3447 | 0.6918 | −0.0472 | 0.022* | |
C31 | 0.52440 (16) | 0.43687 (14) | 0.57897 (10) | 0.0283 (3) | |
H31 | 0.541 | 0.3936 | 0.633 | 0.034* | |
C32 | 0.59078 (16) | 0.42566 (14) | 0.49868 (11) | 0.0293 (3) | |
H32 | 0.6532 | 0.3748 | 0.4977 | 0.035* | |
C33 | 0.43334 (16) | 0.51160 (14) | 0.58070 (11) | 0.0291 (3) | |
H33 | 0.3878 | 0.5197 | 0.6358 | 0.035* |
U11 | U22 | U33 | U12 | U13 | U23 | |
C13 | 0.0132 (5) | 0.0144 (5) | 0.0112 (5) | 0.0050 (4) | −0.0004 (4) | −0.0011 (4) |
Ru1 | 0.01057 (5) | 0.01581 (5) | 0.00970 (5) | 0.00475 (3) | −0.00032 (3) | 0.00017 (3) |
Cl2 | 0.01653 (13) | 0.01590 (12) | 0.01587 (12) | 0.00649 (10) | −0.00139 (10) | 0.00159 (10) |
Cl1 | 0.01180 (12) | 0.01761 (13) | 0.01576 (12) | 0.00284 (10) | −0.00064 (10) | 0.00031 (10) |
P1 | 0.01084 (13) | 0.01358 (13) | 0.01068 (13) | 0.00509 (10) | −0.00095 (10) | −0.00060 (10) |
C21 | 0.0192 (6) | 0.0392 (8) | 0.0191 (6) | 0.0170 (6) | −0.0003 (5) | −0.0004 (5) |
C24 | 0.0154 (6) | 0.0228 (6) | 0.0218 (6) | 0.0060 (5) | 0.0005 (5) | −0.0028 (5) |
C7 | 0.0158 (5) | 0.0138 (5) | 0.0134 (5) | 0.0055 (4) | −0.0009 (4) | 0.0000 (4) |
C3 | 0.0196 (6) | 0.0323 (7) | 0.0105 (5) | 0.0097 (5) | −0.0018 (4) | −0.0046 (5) |
C19 | 0.0121 (5) | 0.0222 (6) | 0.0121 (5) | 0.0067 (4) | −0.0013 (4) | −0.0019 (4) |
C12 | 0.0259 (6) | 0.0163 (5) | 0.0156 (5) | 0.0085 (5) | −0.0024 (5) | −0.0023 (4) |
C15 | 0.0220 (6) | 0.0181 (6) | 0.0152 (5) | 0.0064 (5) | −0.0021 (5) | −0.0037 (4) |
C6 | 0.0143 (6) | 0.0338 (7) | 0.0138 (5) | 0.0065 (5) | 0.0035 (4) | −0.0019 (5) |
C5 | 0.0214 (6) | 0.0282 (7) | 0.0150 (6) | 0.0057 (5) | 0.0069 (5) | 0.0040 (5) |
C9 | 0.0350 (7) | 0.0187 (6) | 0.0165 (6) | 0.0108 (5) | 0.0019 (5) | 0.0030 (5) |
C23 | 0.0160 (6) | 0.0296 (7) | 0.0247 (7) | 0.0008 (5) | 0.0011 (5) | −0.0029 (5) |
C2 | 0.0232 (6) | 0.0252 (6) | 0.0128 (5) | 0.0103 (5) | 0.0004 (5) | −0.0049 (5) |
C1 | 0.0191 (6) | 0.0322 (7) | 0.0128 (5) | 0.0144 (5) | 0.0012 (4) | −0.0027 (5) |
C20 | 0.0181 (6) | 0.0260 (6) | 0.0150 (5) | 0.0107 (5) | 0.0000 (4) | −0.0001 (5) |
C22 | 0.0122 (6) | 0.0445 (8) | 0.0195 (6) | 0.0080 (6) | 0.0002 (5) | −0.0022 (6) |
C4 | 0.0234 (6) | 0.0347 (7) | 0.0100 (5) | 0.0133 (6) | 0.0024 (5) | 0.0042 (5) |
C17 | 0.0179 (6) | 0.0187 (5) | 0.0155 (5) | 0.0086 (5) | 0.0023 (4) | −0.0001 (4) |
C8 | 0.0247 (6) | 0.0181 (6) | 0.0138 (5) | 0.0075 (5) | −0.0029 (5) | 0.0006 (4) |
C29 | 0.0274 (7) | 0.0277 (7) | 0.0265 (7) | −0.0026 (6) | 0.0052 (6) | 0.0001 (6) |
C25 | 0.0208 (7) | 0.0254 (7) | 0.0402 (8) | 0.0026 (5) | −0.0036 (6) | −0.0017 (6) |
C10 | 0.0477 (9) | 0.0177 (6) | 0.0219 (6) | 0.0143 (6) | 0.0010 (6) | 0.0028 (5) |
C30 | 0.0328 (8) | 0.0284 (7) | 0.0251 (7) | 0.0048 (6) | −0.0028 (6) | 0.0004 (6) |
C11 | 0.0376 (8) | 0.0147 (6) | 0.0238 (7) | 0.0066 (5) | −0.0025 (6) | −0.0016 (5) |
C27 | 0.0383 (8) | 0.0232 (6) | 0.0234 (7) | 0.0100 (6) | 0.0012 (6) | −0.0002 (5) |
C28 | 0.0249 (7) | 0.0286 (7) | 0.0280 (7) | 0.0011 (6) | −0.0031 (6) | −0.0057 (6) |
C26 | 0.0276 (7) | 0.0185 (6) | 0.0376 (8) | 0.0036 (5) | 0.0098 (6) | 0.0035 (5) |
C18 | 0.0143 (5) | 0.0154 (5) | 0.0138 (5) | 0.0050 (4) | 0.0018 (4) | −0.0001 (4) |
C14 | 0.0184 (6) | 0.0212 (6) | 0.0148 (5) | 0.0089 (5) | −0.0043 (4) | −0.0049 (4) |
C16 | 0.0237 (6) | 0.0182 (6) | 0.0141 (5) | 0.0094 (5) | 0.0016 (5) | −0.0017 (4) |
C31 | 0.0353 (8) | 0.0228 (6) | 0.0273 (7) | 0.0108 (6) | −0.0125 (6) | −0.0045 (5) |
C32 | 0.0307 (7) | 0.0253 (7) | 0.0353 (8) | 0.0147 (6) | −0.0106 (6) | −0.0079 (6) |
C33 | 0.0328 (8) | 0.0269 (7) | 0.0283 (7) | 0.0106 (6) | −0.0043 (6) | −0.0071 (6) |
C13—C18 | 1.5352 (16) | C23—C22 | 1.393 (2) |
C13—C14 | 1.5422 (15) | C23—H23 | 0.95 |
C13—P1 | 1.8536 (11) | C2—C1 | 1.4111 (18) |
C13—H13 | 1 | C2—H2 | 0.95 |
Ru1—C5 | 2.1708 (13) | C1—H1 | 0.95 |
Ru1—C1 | 2.1808 (12) | C20—H20 | 0.95 |
Ru1—C6 | 2.1816 (13) | C22—H22 | 0.95 |
Ru1—C2 | 2.1919 (12) | C4—H4 | 0.95 |
Ru1—C4 | 2.2667 (12) | C17—C16 | 1.5328 (17) |
Ru1—C3 | 2.2677 (12) | C17—C18 | 1.5333 (16) |
Ru1—P1 | 2.3786 (3) | C17—H17A | 0.99 |
Ru1—Cl1 | 2.4137 (3) | C17—H17B | 0.99 |
Ru1—Cl2 | 2.4239 (3) | C8—H8A | 0.99 |
P1—C19 | 1.8312 (12) | C8—H8B | 0.99 |
P1—C7 | 1.8564 (12) | C29—C28 | 1.387 (2) |
C21—C22 | 1.387 (2) | C29—C30 | 1.389 (2) |
C21—C20 | 1.3993 (18) | C29—H29 | 0.95 |
C21—H21 | 0.95 | C25—C30 | 1.384 (2) |
C24—C23 | 1.3925 (18) | C25—C26 | 1.385 (2) |
C24—C19 | 1.4067 (18) | C25—H25 | 0.95 |
C24—H24 | 0.95 | C10—C11 | 1.5295 (19) |
C7—C12 | 1.5422 (16) | C10—H10A | 0.99 |
C7—C8 | 1.5429 (16) | C10—H10B | 0.99 |
C7—H7 | 1 | C30—H30 | 0.95 |
C3—C4 | 1.388 (2) | C11—H11A | 0.99 |
C3—C2 | 1.4351 (18) | C11—H11B | 0.99 |
C3—H3 | 0.95 | C27—C26 | 1.387 (2) |
C19—C20 | 1.3986 (17) | C27—C28 | 1.387 (2) |
C12—C11 | 1.5318 (18) | C27—H27 | 0.95 |
C12—H12A | 0.99 | C28—H28 | 0.95 |
C12—H12B | 0.99 | C26—H26 | 0.95 |
C15—C16 | 1.5290 (18) | C18—H18A | 0.99 |
C15—C14 | 1.5366 (16) | C18—H18B | 0.99 |
C15—H15A | 0.99 | C14—H14A | 0.99 |
C15—H15B | 0.99 | C14—H14B | 0.99 |
C6—C5 | 1.4074 (19) | C16—H16A | 0.99 |
C6—C1 | 1.426 (2) | C16—H16B | 0.99 |
C6—H6 | 0.95 | C31—C32 | 1.382 (2) |
C5—C4 | 1.4357 (19) | C31—C33 | 1.391 (2) |
C5—H5 | 0.95 | C31—H31 | 0.95 |
C9—C10 | 1.5249 (18) | C32—C33i | 1.391 (2) |
C9—C8 | 1.5330 (18) | C32—H32 | 0.95 |
C9—H9A | 0.99 | C33—C32i | 1.391 (2) |
C9—H9B | 0.99 | C33—H33 | 0.95 |
C18—C13—C14 | 110.24 (9) | H9A—C9—H9B | 107.9 |
C18—C13—P1 | 111.93 (8) | C24—C23—C22 | 120.14 (13) |
C14—C13—P1 | 118.23 (8) | C24—C23—H23 | 119.9 |
C18—C13—H13 | 105.1 | C22—C23—H23 | 119.9 |
C14—C13—H13 | 105.1 | C1—C2—C3 | 119.86 (12) |
P1—C13—H13 | 105.1 | C1—C2—Ru1 | 70.74 (7) |
C5—Ru1—C1 | 68.40 (5) | C3—C2—Ru1 | 74.12 (7) |
C5—Ru1—C6 | 37.73 (5) | C1—C2—H2 | 120.1 |
C1—Ru1—C6 | 38.15 (5) | C3—C2—H2 | 120.1 |
C5—Ru1—C2 | 80.54 (5) | Ru1—C2—H2 | 127 |
C1—Ru1—C2 | 37.65 (5) | C2—C1—C6 | 119.93 (12) |
C6—Ru1—C2 | 68.32 (5) | C2—C1—Ru1 | 71.60 (7) |
C5—Ru1—C4 | 37.68 (5) | C6—C1—Ru1 | 70.96 (7) |
C1—Ru1—C4 | 79.39 (5) | C2—C1—H1 | 120 |
C6—Ru1—C4 | 67.44 (5) | C6—C1—H1 | 120 |
C2—Ru1—C4 | 66.63 (5) | Ru1—C1—H1 | 129.9 |
C5—Ru1—C3 | 66.62 (5) | C19—C20—C21 | 120.63 (13) |
C1—Ru1—C3 | 67.21 (5) | C19—C20—H20 | 119.7 |
C6—Ru1—C3 | 79.24 (5) | C21—C20—H20 | 119.7 |
C2—Ru1—C3 | 37.50 (5) | C21—C22—C23 | 119.51 (12) |
C4—Ru1—C3 | 35.64 (5) | C21—C22—H22 | 120.2 |
C5—Ru1—P1 | 121.28 (4) | C23—C22—H22 | 120.2 |
C1—Ru1—P1 | 90.39 (3) | C3—C4—C5 | 119.47 (12) |
C6—Ru1—P1 | 93.12 (3) | C3—C4—Ru1 | 72.22 (7) |
C2—Ru1—P1 | 115.10 (3) | C5—C4—Ru1 | 67.54 (7) |
C4—Ru1—P1 | 158.87 (4) | C3—C4—H4 | 120.3 |
C3—Ru1—P1 | 152.44 (4) | C5—C4—H4 | 120.3 |
C5—Ru1—Cl1 | 151.18 (4) | Ru1—C4—H4 | 133 |
C1—Ru1—Cl1 | 120.39 (4) | C16—C17—C18 | 111.25 (10) |
C6—Ru1—Cl1 | 158.52 (4) | C16—C17—H17A | 109.4 |
C2—Ru1—Cl1 | 92.13 (4) | C18—C17—H17A | 109.4 |
C4—Ru1—Cl1 | 114.00 (4) | C16—C17—H17B | 109.4 |
C3—Ru1—Cl1 | 90.67 (4) | C18—C17—H17B | 109.4 |
P1—Ru1—Cl1 | 87.124 (11) | H17A—C17—H17B | 108 |
C5—Ru1—Cl2 | 86.78 (4) | C9—C8—C7 | 111.20 (10) |
C1—Ru1—Cl2 | 151.53 (4) | C9—C8—H8A | 109.4 |
C6—Ru1—Cl2 | 113.39 (4) | C7—C8—H8A | 109.4 |
C2—Ru1—Cl2 | 153.91 (3) | C9—C8—H8B | 109.4 |
C4—Ru1—Cl2 | 89.50 (4) | C7—C8—H8B | 109.4 |
C3—Ru1—Cl2 | 116.42 (3) | H8A—C8—H8B | 108 |
P1—Ru1—Cl2 | 90.969 (10) | C28—C29—C30 | 119.92 (14) |
Cl1—Ru1—Cl2 | 88.071 (11) | C28—C29—H29 | 120 |
C19—P1—C13 | 103.21 (5) | C30—C29—H29 | 120 |
C19—P1—C7 | 110.18 (5) | C30—C25—C26 | 120.13 (14) |
C13—P1—C7 | 106.93 (5) | C30—C25—H25 | 119.9 |
C19—P1—Ru1 | 109.13 (4) | C26—C25—H25 | 119.9 |
C13—P1—Ru1 | 113.89 (4) | C9—C10—C11 | 111.01 (11) |
C7—P1—Ru1 | 113.03 (4) | C9—C10—H10A | 109.4 |
C22—C21—C20 | 120.56 (12) | C11—C10—H10A | 109.4 |
C22—C21—H21 | 119.7 | C9—C10—H10B | 109.4 |
C20—C21—H21 | 119.7 | C11—C10—H10B | 109.4 |
C23—C24—C19 | 121.02 (12) | H10A—C10—H10B | 108 |
C23—C24—H24 | 119.5 | C25—C30—C29 | 119.91 (14) |
C19—C24—H24 | 119.5 | C25—C30—H30 | 120 |
C12—C7—C8 | 110.59 (9) | C29—C30—H30 | 120 |
C12—C7—P1 | 114.10 (8) | C10—C11—C12 | 111.49 (12) |
C8—C7—P1 | 115.61 (8) | C10—C11—H11A | 109.3 |
C12—C7—H7 | 105.1 | C12—C11—H11A | 109.3 |
C8—C7—H7 | 105.1 | C10—C11—H11B | 109.3 |
P1—C7—H7 | 105.1 | C12—C11—H11B | 109.3 |
C4—C3—C2 | 120.40 (12) | H11A—C11—H11B | 108 |
C4—C3—Ru1 | 72.14 (7) | C26—C27—C28 | 119.83 (14) |
C2—C3—Ru1 | 68.39 (7) | C26—C27—H27 | 120.1 |
C4—C3—H3 | 119.8 | C28—C27—H27 | 120.1 |
C2—C3—H3 | 119.8 | C27—C28—C29 | 120.08 (14) |
Ru1—C3—H3 | 132.8 | C27—C28—H28 | 120 |
C20—C19—C24 | 118.14 (11) | C29—C28—H28 | 120 |
C20—C19—P1 | 124.07 (10) | C25—C26—C27 | 120.12 (14) |
C24—C19—P1 | 117.23 (9) | C25—C26—H26 | 119.9 |
C11—C12—C7 | 110.46 (10) | C27—C26—H26 | 119.9 |
C11—C12—H12A | 109.6 | C17—C18—C13 | 109.57 (10) |
C7—C12—H12A | 109.6 | C17—C18—H18A | 109.8 |
C11—C12—H12B | 109.6 | C13—C18—H18A | 109.8 |
C7—C12—H12B | 109.6 | C17—C18—H18B | 109.8 |
H12A—C12—H12B | 108.1 | C13—C18—H18B | 109.8 |
C16—C15—C14 | 111.35 (10) | H18A—C18—H18B | 108.2 |
C16—C15—H15A | 109.4 | C15—C14—C13 | 109.76 (10) |
C14—C15—H15A | 109.4 | C15—C14—H14A | 109.7 |
C16—C15—H15B | 109.4 | C13—C14—H14A | 109.7 |
C14—C15—H15B | 109.4 | C15—C14—H14B | 109.7 |
H15A—C15—H15B | 108 | C13—C14—H14B | 109.7 |
C5—C6—C1 | 119.38 (12) | H14A—C14—H14B | 108.2 |
C5—C6—Ru1 | 70.72 (7) | C15—C16—C17 | 111.11 (10) |
C1—C6—Ru1 | 70.89 (7) | C15—C16—H16A | 109.4 |
C5—C6—H6 | 120.3 | C17—C16—H16A | 109.4 |
C1—C6—H6 | 120.3 | C15—C16—H16B | 109.4 |
Ru1—C6—H6 | 130.6 | C17—C16—H16B | 109.4 |
C6—C5—C4 | 120.66 (13) | H16A—C16—H16B | 108 |
C6—C5—Ru1 | 71.55 (7) | C32—C31—C33 | 119.98 (14) |
C4—C5—Ru1 | 74.79 (7) | C32—C31—H31 | 120 |
C6—C5—H5 | 119.7 | C33—C31—H31 | 120 |
C4—C5—H5 | 119.7 | C31—C32—C33i | 120.33 (14) |
Ru1—C5—H5 | 125.8 | C31—C32—H32 | 119.8 |
C10—C9—C8 | 111.74 (11) | C33i—C32—H32 | 119.8 |
C10—C9—H9A | 109.3 | C32i—C33—C31 | 119.69 (15) |
C8—C9—H9A | 109.3 | C32i—C33—H33 | 120.2 |
C10—C9—H9B | 109.3 | C31—C33—H33 | 120.2 |
C8—C9—H9B | 109.3 | ||
C18—C13—P1—C19 | 169.93 (8) | P1—Ru1—C5—C4 | −177.46 (6) |
C14—C13—P1—C19 | 40.18 (10) | Cl1—Ru1—C5—C4 | 13.27 (13) |
C18—C13—P1—C7 | 53.70 (9) | Cl2—Ru1—C5—C4 | 93.36 (7) |
C14—C13—P1—C7 | −76.05 (10) | C19—C24—C23—C22 | −0.8 (2) |
C18—C13—P1—Ru1 | −71.90 (8) | C4—C3—C2—C1 | 3.99 (18) |
C14—C13—P1—Ru1 | 158.35 (8) | Ru1—C3—C2—C1 | 56.04 (10) |
C5—Ru1—P1—C19 | 21.52 (6) | C4—C3—C2—Ru1 | −52.05 (11) |
C1—Ru1—P1—C19 | −43.22 (6) | C5—Ru1—C2—C1 | −66.72 (8) |
C6—Ru1—P1—C19 | −5.15 (6) | C6—Ru1—C2—C1 | −29.53 (8) |
C2—Ru1—P1—C19 | −72.63 (6) | C4—Ru1—C2—C1 | −103.39 (9) |
C4—Ru1—P1—C19 | 17.21 (11) | C3—Ru1—C2—C1 | −130.37 (12) |
C3—Ru1—P1—C19 | −77.71 (9) | P1—Ru1—C2—C1 | 53.49 (8) |
Cl1—Ru1—P1—C19 | −163.64 (4) | Cl1—Ru1—C2—C1 | 141.32 (7) |
Cl2—Ru1—P1—C19 | 108.34 (4) | Cl2—Ru1—C2—C1 | −128.72 (8) |
C5—Ru1—P1—C13 | −93.20 (6) | C5—Ru1—C2—C3 | 63.64 (8) |
C1—Ru1—P1—C13 | −157.94 (6) | C1—Ru1—C2—C3 | 130.37 (12) |
C6—Ru1—P1—C13 | −119.87 (6) | C6—Ru1—C2—C3 | 100.84 (9) |
C2—Ru1—P1—C13 | 172.65 (6) | C4—Ru1—C2—C3 | 26.98 (8) |
C4—Ru1—P1—C13 | −97.51 (11) | P1—Ru1—C2—C3 | −176.14 (7) |
C3—Ru1—P1—C13 | 167.57 (8) | Cl1—Ru1—C2—C3 | −88.32 (8) |
Cl1—Ru1—P1—C13 | 81.64 (4) | Cl2—Ru1—C2—C3 | 1.64 (14) |
Cl2—Ru1—P1—C13 | −6.38 (4) | C3—C2—C1—C6 | −3.71 (18) |
C5—Ru1—P1—C7 | 144.49 (6) | Ru1—C2—C1—C6 | 53.97 (10) |
C1—Ru1—P1—C7 | 79.75 (6) | C3—C2—C1—Ru1 | −57.67 (10) |
C6—Ru1—P1—C7 | 117.83 (6) | C5—C6—C1—C2 | −0.86 (18) |
C2—Ru1—P1—C7 | 50.34 (6) | Ru1—C6—C1—C2 | −54.27 (10) |
C4—Ru1—P1—C7 | 140.19 (11) | C5—C6—C1—Ru1 | 53.41 (10) |
C3—Ru1—P1—C7 | 45.26 (9) | C5—Ru1—C1—C2 | 102.95 (9) |
Cl1—Ru1—P1—C7 | −40.66 (4) | C6—Ru1—C1—C2 | 132.15 (11) |
Cl2—Ru1—P1—C7 | −128.68 (4) | C4—Ru1—C1—C2 | 65.31 (8) |
C19—P1—C7—C12 | 80.39 (9) | C3—Ru1—C1—C2 | 30.20 (8) |
C13—P1—C7—C12 | −168.11 (8) | P1—Ru1—C1—C2 | −133.29 (7) |
Ru1—P1—C7—C12 | −41.99 (9) | Cl1—Ru1—C1—C2 | −46.40 (8) |
C19—P1—C7—C8 | −49.53 (10) | Cl2—Ru1—C1—C2 | 133.96 (7) |
C13—P1—C7—C8 | 61.97 (10) | C5—Ru1—C1—C6 | −29.20 (7) |
Ru1—P1—C7—C8 | −171.91 (7) | C2—Ru1—C1—C6 | −132.15 (11) |
C5—Ru1—C3—C4 | 28.75 (8) | C4—Ru1—C1—C6 | −66.84 (8) |
C1—Ru1—C3—C4 | 104.07 (9) | C3—Ru1—C1—C6 | −101.94 (8) |
C6—Ru1—C3—C4 | 66.10 (8) | P1—Ru1—C1—C6 | 94.57 (7) |
C2—Ru1—C3—C4 | 134.39 (12) | Cl1—Ru1—C1—C6 | −178.54 (6) |
P1—Ru1—C3—C4 | 141.96 (7) | Cl2—Ru1—C1—C6 | 1.81 (12) |
Cl1—Ru1—C3—C4 | −132.98 (7) | C24—C19—C20—C21 | 0.37 (18) |
Cl2—Ru1—C3—C4 | −44.80 (8) | P1—C19—C20—C21 | −170.69 (10) |
C5—Ru1—C3—C2 | −105.64 (9) | C22—C21—C20—C19 | −0.27 (19) |
C1—Ru1—C3—C2 | −30.32 (8) | C20—C21—C22—C23 | −0.4 (2) |
C6—Ru1—C3—C2 | −68.29 (8) | C24—C23—C22—C21 | 0.9 (2) |
C4—Ru1—C3—C2 | −134.39 (12) | C2—C3—C4—C5 | 0.32 (18) |
P1—Ru1—C3—C2 | 7.57 (13) | Ru1—C3—C4—C5 | −50.06 (10) |
Cl1—Ru1—C3—C2 | 92.63 (8) | C2—C3—C4—Ru1 | 50.38 (11) |
Cl2—Ru1—C3—C2 | −179.19 (7) | C6—C5—C4—C3 | −4.96 (18) |
C23—C24—C19—C20 | 0.15 (18) | Ru1—C5—C4—C3 | 52.19 (11) |
C23—C24—C19—P1 | 171.83 (10) | C6—C5—C4—Ru1 | −57.14 (10) |
C13—P1—C19—C20 | −142.05 (10) | C5—Ru1—C4—C3 | −133.75 (12) |
C7—P1—C19—C20 | −28.16 (12) | C1—Ru1—C4—C3 | −65.49 (8) |
Ru1—P1—C19—C20 | 96.50 (10) | C6—Ru1—C4—C3 | −103.44 (9) |
C13—P1—C19—C24 | 46.81 (11) | C2—Ru1—C4—C3 | −28.28 (8) |
C7—P1—C19—C24 | 160.70 (9) | P1—Ru1—C4—C3 | −127.73 (10) |
Ru1—P1—C19—C24 | −74.64 (10) | Cl1—Ru1—C4—C3 | 53.20 (8) |
C8—C7—C12—C11 | −56.30 (14) | Cl2—Ru1—C4—C3 | 140.87 (7) |
P1—C7—C12—C11 | 171.32 (9) | C1—Ru1—C4—C5 | 68.27 (8) |
C1—Ru1—C6—C5 | −132.16 (11) | C6—Ru1—C4—C5 | 30.32 (8) |
C2—Ru1—C6—C5 | −102.99 (9) | C2—Ru1—C4—C5 | 105.47 (9) |
C4—Ru1—C6—C5 | −30.27 (8) | C3—Ru1—C4—C5 | 133.75 (12) |
C3—Ru1—C6—C5 | −65.51 (8) | P1—Ru1—C4—C5 | 6.03 (15) |
P1—Ru1—C6—C5 | 141.19 (7) | Cl1—Ru1—C4—C5 | −173.04 (7) |
Cl1—Ru1—C6—C5 | −128.73 (9) | Cl2—Ru1—C4—C5 | −85.38 (8) |
Cl2—Ru1—C6—C5 | 48.78 (8) | C10—C9—C8—C7 | −55.01 (15) |
C5—Ru1—C6—C1 | 132.16 (11) | C12—C7—C8—C9 | 55.45 (14) |
C2—Ru1—C6—C1 | 29.17 (7) | P1—C7—C8—C9 | −172.95 (9) |
C4—Ru1—C6—C1 | 101.89 (8) | C8—C9—C10—C11 | 55.02 (17) |
C3—Ru1—C6—C1 | 66.65 (7) | C26—C25—C30—C29 | 0.5 (2) |
P1—Ru1—C6—C1 | −86.65 (7) | C28—C29—C30—C25 | 0.2 (2) |
Cl1—Ru1—C6—C1 | 3.44 (14) | C9—C10—C11—C12 | −56.16 (17) |
Cl2—Ru1—C6—C1 | −179.06 (6) | C7—C12—C11—C10 | 56.94 (15) |
C1—C6—C5—C4 | 5.21 (18) | C26—C27—C28—C29 | 0.3 (2) |
Ru1—C6—C5—C4 | 58.71 (11) | C30—C29—C28—C27 | −0.6 (2) |
C1—C6—C5—Ru1 | −53.49 (10) | C30—C25—C26—C27 | −0.7 (2) |
C1—Ru1—C5—C6 | 29.50 (8) | C28—C27—C26—C25 | 0.3 (2) |
C2—Ru1—C5—C6 | 66.63 (8) | C16—C17—C18—C13 | 57.64 (13) |
C4—Ru1—C5—C6 | 130.38 (12) | C14—C13—C18—C17 | −59.41 (12) |
C3—Ru1—C5—C6 | 103.09 (9) | P1—C13—C18—C17 | 166.81 (8) |
P1—Ru1—C5—C6 | −47.08 (9) | C16—C15—C14—C13 | −56.64 (13) |
Cl1—Ru1—C5—C6 | 143.65 (7) | C18—C13—C14—C15 | 58.94 (13) |
Cl2—Ru1—C5—C6 | −136.26 (8) | P1—C13—C14—C15 | −170.54 (8) |
C1—Ru1—C5—C4 | −100.88 (9) | C14—C15—C16—C17 | 55.08 (13) |
C6—Ru1—C5—C4 | −130.38 (12) | C18—C17—C16—C15 | −55.60 (13) |
C2—Ru1—C5—C4 | −63.75 (8) | C33—C31—C32—C33i | −0.2 (2) |
C3—Ru1—C5—C4 | −27.30 (8) | C32—C31—C33—C32i | 0.2 (2) |
Symmetry code: (i) −x+1, −y+1, −z+1. |
Cg1 and Cg2 are the centroids of the C19–C24 and C31–C33/C31'–C33') benzene rings. |
D—H···A | D—H | H···A | D···A | D—H···A |
C3—H3···Cl2ii | 0.95 | 2.76 | 3.6307 (13) | 153 |
C4—H4···Cl1ii | 0.95 | 2.7 | 3.6209 (13) | 163 |
C6—H6···Cg1 | 0.95 | 2.78 | 3.5086 (14) | 135 |
C2—H2···Cg2iii | 0.95 | 2.73 | 3.5869 (15) | 150 |
Symmetry codes: (ii) −x+1, −y+2, −z+1; (iii) x, y+1, z. |
Experimental details
Crystal data | |
Chemical formula | [RuCl2(C6H6)(C18H27P)]·1.5C6H6 |
Mr | 641.61 |
Crystal system, space group | Triclinic, P1 |
Temperature (K) | 100 |
a, b, c (Å) | 10.0893 (8), 10.8325 (9), 14.4937 (12) |
α, β, γ (°) | 90.346 (2), 91.748 (1), 106.979 (1) |
V (Å3) | 1514.1 (2) |
Z | 2 |
Radiation type | Mo Kα |
µ (mm−1) | 0.77 |
Crystal size (mm) | 0.43 × 0.17 × 0.16 |
Data collection | |
Diffractometer | Bruker APEX DUO 4K CCD diffractometer |
Absorption correction | Multi-scan (SADABS; Bruker, 2008) |
Tmin, Tmax | 0.734, 0.887 |
No. of measured, independent and observed [I > 2σ(I)] reflections | 49345, 7589, 7093 |
Rint | 0.022 |
(sin θ/λ)max (Å−1) | 0.669 |
Refinement | |
R[F2 > 2σ(F2)], wR(F2), S | 0.018, 0.048, 1.03 |
No. of reflections | 7589 |
No. of parameters | 334 |
H-atom treatment | H-atom parameters constrained |
Δρmax, Δρmin (e Å−3) | 0.54, −0.43 |
Computer programs: APEX2 (Bruker, 2011), SAINT (Bruker, 2008), SAINT and XPREP (Bruker, 2008), SIR97 (Altomare et al., 1999), SHELXL97 (Sheldrick, 2008), DIAMOND (Brandenburg & Putz, 2005), publCIF (Westrip, 2010) and WinGX (Farrugia, 1999).
Cg1 and Cg2 are the centroids of the C19–C24 and C31–C33/C31'–C33') benzene rings. |
D—H···A | D—H | H···A | D···A | D—H···A |
C3—H3···Cl2i | 0.95 | 2.76 | 3.6307 (13) | 153.4 |
C4—H4···Cl1i | 0.95 | 2.7 | 3.6209 (13) | 162.9 |
C6—H6···Cg1 | 0.95 | 2.78 | 3.5086 (14) | 135 |
C2—H2···Cg2ii | 0.95 | 2.73 | 3.5869 (15) | 150 |
Symmetry codes: (i) −x+1, −y+2, −z+1; (ii) x, y+1, z. |
Acknowledgements
Financial assistance from the Research Fund of the University of Johannesburg is gratefully acknowledged.
References
Allen, F. H. (2002). Acta Cryst. B58, 380–388. Web of Science CrossRef CAS IUCr Journals Google Scholar
Altomare, A., Burla, M. C., Camalli, M., Cascarano, G. L., Giacovazzo, C., Guagliardi, A., Moliterni, A. G. G., Polidori, G. & Spagna, R. (1999). J. Appl. Cryst. 32, 115–119. Web of Science CrossRef CAS IUCr Journals Google Scholar
Aydemir, M., Baysal, A., Meric, N., Kayan, C., Gümgüm, B., Özkar, S. & Şahin, E. (2011). Inorg. Chim. Acta, 356, 114–120. Google Scholar
Brandenburg, K. & Putz, H. (2005). DIAMOND. Crystal Impact GbR, Bonn, Germany. Google Scholar
Bruker (2008). SADABS, SAINT and XPREP. Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
Bruker (2011). APEX2. Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
Chen, Y., Valentini, M., Pregosin, P. S. & Albinati, A. (2002). Inorg. Chim. Acta, 327, 4–14. Web of Science CSD CrossRef CAS Google Scholar
Crochet, P., Fernández-Zumel, M. A., Beauquis, C. & Gimeno, J. (2003). Inorg. Chim. Acta, 356, 114–120. Web of Science CrossRef CAS Google Scholar
Farrugia, L. J. (1999). J. Appl. Cryst. 32, 837–838. CrossRef CAS IUCr Journals Google Scholar
Otto, S. (2001). Acta Cryst. C57, 793–795. Web of Science CSD CrossRef CAS IUCr Journals Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar
Stumpf, A. W., Saive, E., Demonceau, A. & Noels, A. F. (1995). J. Chem. Soc. Chem. Commun. pp. 1127–1128. CrossRef Web of Science Google Scholar
Tolman, C. A. (1977). Chem. Rev. 77, 313–348. CrossRef CAS Web of Science Google Scholar
Wang, L., Yang, Q., Fu, H.-Y., Chen, H., Yuan, M.-L. & Li, R.-X. (2011). Appl. Organomet. Chem. 25, 626–631. Web of Science CSD CrossRef CAS Google Scholar
Westrip, S. P. (2010). J. Appl. Cryst. 43, 920–925. Web of Science CrossRef CAS IUCr Journals Google Scholar
This is an open-access article distributed under the terms of the Creative Commons Attribution (CC-BY) Licence, which permits unrestricted use, distribution, and reproduction in any medium, provided the original authors and source are cited.
The activity of the half-sandwich Ru(II)-arene complexes are well known in the catalytic transfer hydrogenation of carbonyl compounds (Chen et al., 2002; Crochet et al., 2003; Aydemir et al., 2011; Wang et al., 2011) and for ring-opening metathesis polymerization (Stumpf et al., 1995). Reported here is the η6-Ru compound containing the phosphane, PCy2Ph, where Cy = C6H11 and Ph = C6H5 as part of our ongoing structural investigation into these type of complexes.
The title compound crystallizes in the triclinic space group P1 (Z=2), with its molecules adopting a classical three-legged piano-stool environment observed for these type of complexes. Each Ru complex co-crystallizes with sesqui benzene solvate molecules due to one of the solvate being situated on an inversion centre (see Fig. 1). The coordination sphere of the ruthenium is occupied by a benzene, dicyclohexylphenylphosphane and two chloride atoms. The distance between Ru and the centroid of the π-bonded η6-benzene ligand is 1.6964 (6) Å and the mean Ru—C bond distance is 2.2099 (13) Å. The coordination of the remaining ligands to the Ru atom shows a slight deviation from the typical octahedral geometry with Cl—Ru—Cl = 88.07 (11) and Cl—Ru—P = 87.12 (11), 90.97 (2)°. The bond distances of Ru—P = 2.3786 (3) and Ru—Cl(avg.) = 2.4138 (3) Å are within normal ranges (Allen, 2002).
The steric demand of phosphane ligands is usually described with the use of the Tolman cone angle model (Tolman, 1977). In the present study we make use of an adaptation of this model whereby the geometry obtained from the title compound (and adjusting the Ru—P bond distance to 2.28 Å) is used to calculate an effective cone angle (Otto, 2001). The value obtained with this method is 158°, which is marginally smaller that the average effective cone angle value calculated from literature observations of the phosphane ligand. Data extracted from the Cambridge Structural Database (Allen, 2002) shows an average cone angle of 165° for the phosphane from 31 hits, containing 45 useable observations with a standard deviation of ±6° and a spread from 148° to 180°.
The slightly smaller cone angle value obtained for the phosphane ligand in the title compound could be due to a crowded metal coordination environment as well as several C–H···Cl and C–H···π interactions that are observed (see Fig. 2, Table 1 for a graphical representation of the interactions).