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The crystal structure of the title compound, chloro(η5-cyclopenta­dienyl){(1R,2S)-2-[(di­phenyl­phosphino)­methyl­amino]-1-phenyl­propyl di­phenyl­phosphinite-κ2P,P′}ruthenium(II), [Ru(C5H5)Cl(C34H33NOP2)], is reported. The pseudo-octa­hedral complex is chiral and the configuration at the Ru atom is S. The seven-membered metallacycle adopts a boat-like conformation.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S0108270102018395/gd1228sup1.cif
Contains datablocks global, I

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S0108270102018395/gd1228Isup2.hkl
Contains datablock I

CCDC reference: 199412

Comment top

Organometallic complexes containing a chiral metal centre have attracted considerable attention, due to their potential application as reagents in asymmetric synthesis (Brunner, 1999). For this purpose, half-sandwich Cp—Ru complexes bearing a chelating diphosphine without C2v symmetry are attractive targets, since these species have been shown to be configurationally stable at the chiral metal centre (Davies et al., 1990). Here, we present the molecular structure of the title complex, (I), a new optically pure half-sandwich Ru complex, which was obtained by reaction of the diphosphine (+)-(2S,3R)-2-[(diphenylphosphino)methylamino]-3-phenylpropyl diphenylphosphinite with ClRuCpPPh3. \sch

Compound (I) was synthesized as a single diastereomer and crystallized from a pentane-CH2Cl2 solvent mixture in the chiral space group P212121. Our X-ray data allowed determination of the absolute configuration at the Ru centre in (I). The molecular structure of (I) is shown in Fig. 1 and selected dimensions are given in Table 1.

The Ru atom in complex (I) adopts a pseudo-octahedral coordination geometry, which can also be described as a distorted tetrahedral structure if one simplifies the Ru(η5-C5H5) moiety to an Ru—Cg (Cg is the Cp centroid) moiety. The P1—Ru—P2, P1—Ru—Cl and P2—Ru—Cl bond angles [mean 93.76 (3)°] are smaller than the ideal tetrahedral angle (109.47°), which is compensated for by the opening of the Cp—Ru—L L is what? angles [122.44 (15)°]. In accordance with the stereochemical convention adopted for organometallics (Brunner et al., 1980), the ligand priority is C5H5 Cl P(O) P(N) and the absolute configuration of the metal centre is S. The seven-membered Ru-ligand chelate ring adopts a boat-like conformation, with the O atom being very close to the Ru—P1—P2 plane, as shown by the small O—P1—Ru—P2 torsion angle (-5.0°). The N atom is clearly out of the Ru—P1—P2 plane (P2—Ru—P1—N 42.6°).

The Ru—P(N) and Ru—P(O) bond distances [2.2906 (8) and 2.2675 (8) Å, respectively] are slightly longer than those in the related complex (S)—Ru(η5-C5H5)[(S)-dpompyr-PP']Cl [2.269 (2) and 2.242 Å, respectively; dpompyr-PP' is?; Cesarotti et al., 1987]. The Ru—P(N) distance is longer than the Ru—P(O) distance, as is generally observed in transition metal complexes containing aminophosphine-phosphinite ligands (Cesarotti et al., 1987, 1992).

Experimental top

Compound (I) was synthesized by reaction of the (+)-EPHOS ligand (2.670 g, 5 mmol) with CpRu(PPh3)2Cl (1.815 g, 2.5 mmol) in refluxing toluene (20 ml) for 18 h. Purification of the crude product by flash chromatography (CH2Cl2) afforded pure (I) (1.164 g, 63%) as an orange solid. Recrystallization from a dichloromethane-hexane mixture (1:1) afforded orange crystals Please clarify - blue given below suitable for X-ray analysis.

Refinement top

H atoms were treated as riding, with C—H distances in the range 0.93–0.98 Å. Is this added text OK?

Computing details top

Data collection: SMART (Bruker, 2001); cell refinement: SMART; data reduction: SHELXTL (Bruker, 2001); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL.

Figures top
[Figure 1] Fig. 1. A view of the molecular structure of complex (I). Displacement ellipsoids are shown at the 30% probability level and H atoms have been omitted for clarity.
chloro(η5-cyclopentadienyl)-(+)-{(2S,3R)-2-[(diphenylphosphino)methylamino]- 3-phenylpropyl diphenylphosphinite-κ2P,P'}ruthenium(II) top
Crystal data top
[Ru(C5H5)Cl(C34H33NOP2)]F(000) = 1512
Mr = 735.16Dx = 1.375 Mg m3
Orthorhombic, P212121Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2ac 2abCell parameters from 14894 reflections
a = 13.2734 (1) Åθ = 1.8–30.0°
b = 14.3376 (1) ŵ = 0.64 mm1
c = 18.6640 (2) ÅT = 296 K
V = 3551.92 (5) Å3Parallelepiped, blue
Z = 40.30 × 0.28 × 0.14 mm
Data collection top
Make Model CCD area-detector
diffractometer
9351 independent reflections
Radiation source: fine-focus sealed tube6619 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.044
ϕ and ω scansθmax = 30.0°, θmin = 1.8°
Absorption correction: multi-scan
(SADABS; Sheldrick, 1996)
h = 1813
Tmin = 0.832, Tmax = 0.916k = 1819
25398 measured reflectionsl = 2224
Refinement top
Refinement on F2Hydrogen site location: inferred from neighbouring sites
Least-squares matrix: fullH-atom parameters constrained
R[F2 > 2σ(F2)] = 0.038 w = 1/[σ2(Fo2) + (0.0316P)2]
where P = (Fo2 + 2Fc2)/3
wR(F2) = 0.078(Δ/σ)max = 0.015
S = 1.01Δρmax = 0.37 e Å3
9351 reflectionsΔρmin = 0.59 e Å3
409 parametersExtinction correction: SHELXL97 (Sheldrick, 1997), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
0 restraintsExtinction coefficient: 0.00095 (12)
Primary atom site location: structure-invariant direct methodsAbsolute structure: Flack (1983), with 3652 Friedel pairs Query
Secondary atom site location: difference Fourier mapAbsolute structure parameter: 0.03 (2)
Crystal data top
[Ru(C5H5)Cl(C34H33NOP2)]V = 3551.92 (5) Å3
Mr = 735.16Z = 4
Orthorhombic, P212121Mo Kα radiation
a = 13.2734 (1) ŵ = 0.64 mm1
b = 14.3376 (1) ÅT = 296 K
c = 18.6640 (2) Å0.30 × 0.28 × 0.14 mm
Data collection top
Make Model CCD area-detector
diffractometer
9351 independent reflections
Absorption correction: multi-scan
(SADABS; Sheldrick, 1996)
6619 reflections with I > 2σ(I)
Tmin = 0.832, Tmax = 0.916Rint = 0.044
25398 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.038H-atom parameters constrained
wR(F2) = 0.078Δρmax = 0.37 e Å3
S = 1.01Δρmin = 0.59 e Å3
9351 reflectionsAbsolute structure: Flack (1983), with 3652 Friedel pairs Query
409 parametersAbsolute structure parameter: 0.03 (2)
0 restraints
Special details top

Experimental. NMR data for (I). 31P NMR (162 MHz, CDCl3): 141.6 (d, J = 69.3 Hz), 116.4 (d, J = 69.3 Hz). 1H NMR (400 MHz, CDCl3): 8.09 (m, 2H), 7.80 (m, 2H), 7.6–7.1 (m, 17H), 7.07 (t, J = 7.2 Hz, 2H), 6.94 (d, J = 7.2 Hz, 2H), 5.42 (m, 1H), 4.60 (bs, 1H), 4.09 (s, 5H), 1.84 (d, J = 7.6 Hz, 3H), 1.03 (d, J = 6.8 Hz, 3H).

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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
Ru0.229564 (19)0.152984 (16)0.790951 (14)0.04018 (7)
P10.35701 (6)0.24549 (5)0.74856 (4)0.03655 (17)
P20.11931 (5)0.20328 (5)0.70658 (5)0.03585 (16)
Cl0.18925 (7)0.26810 (6)0.88273 (5)0.0595 (2)
O0.15088 (16)0.28621 (13)0.65111 (11)0.0410 (5)
N0.33216 (17)0.35627 (16)0.72425 (13)0.0414 (6)
C10.4254 (2)0.1981 (2)0.67102 (18)0.0471 (8)
C20.3710 (3)0.1468 (3)0.62076 (19)0.0629 (10)
H20.30350.13340.62910.075*
C30.4168 (4)0.1155 (4)0.5585 (2)0.0898 (15)
H30.37940.08260.52480.108*
C40.5170 (4)0.1328 (4)0.5463 (3)0.1032 (18)
H40.54760.11090.50480.124*
C50.5708 (4)0.1817 (4)0.5946 (3)0.1038 (19)
H50.63880.19310.58640.125*
C60.5257 (3)0.2151 (3)0.6564 (2)0.0737 (12)
H60.56380.24960.68880.088*
C70.4569 (2)0.2556 (2)0.81635 (16)0.0438 (8)
C80.5259 (3)0.1846 (3)0.8276 (2)0.0586 (10)
H80.52800.13450.79610.070*
C90.5919 (3)0.1872 (3)0.8853 (2)0.0737 (12)
H90.63690.13840.89260.088*
C100.5912 (3)0.2608 (4)0.9310 (2)0.0822 (14)
H100.63520.26240.96980.099*
C110.5242 (3)0.3335 (4)0.9193 (2)0.0883 (14)
H110.52440.38450.95000.106*
C120.4570 (3)0.3312 (3)0.8627 (2)0.0645 (11)
H120.41200.38010.85580.077*
C130.2312 (2)0.39628 (18)0.73452 (15)0.0376 (6)
H130.20030.36110.77380.045*
C140.1614 (2)0.38363 (19)0.66942 (17)0.0397 (7)
H140.09460.40790.68200.048*
C150.1954 (2)0.4311 (2)0.60154 (17)0.0435 (8)
C160.2613 (3)0.3889 (2)0.55473 (18)0.0554 (9)
H160.28490.32930.56490.066*
C170.2934 (3)0.4335 (3)0.4925 (2)0.0740 (12)
H170.33770.40370.46140.089*
C180.2595 (4)0.5210 (3)0.4774 (2)0.0840 (14)
H180.28170.55120.43610.101*
C190.1936 (4)0.5649 (3)0.5221 (2)0.0790 (14)
H190.17030.62430.51090.095*
C200.1605 (3)0.5201 (2)0.5853 (2)0.0609 (10)
H200.11570.55000.61600.073*
C210.0096 (2)0.2360 (2)0.73185 (18)0.0463 (8)
C220.0778 (3)0.2623 (2)0.6790 (2)0.0617 (10)
H220.05610.26710.63180.074*
C230.1772 (3)0.2812 (2)0.6953 (3)0.0743 (13)
H230.22210.29780.65920.089*
C240.2094 (3)0.2754 (3)0.7654 (3)0.0787 (14)
H240.27620.28850.77670.094*
C250.1438 (3)0.2506 (3)0.8181 (3)0.0761 (12)
H250.16590.24710.86530.091*
C260.0431 (3)0.2305 (2)0.8016 (2)0.0573 (9)
H260.00130.21330.83780.069*
C270.0879 (2)0.1185 (2)0.63631 (18)0.0438 (8)
C280.0351 (3)0.0382 (2)0.6554 (2)0.0592 (10)
H280.01450.02990.70250.071*
C290.0130 (3)0.0297 (3)0.6044 (3)0.0756 (13)
H290.02130.08360.61760.091*
C300.0419 (4)0.0167 (3)0.5345 (3)0.0924 (16)
H300.02680.06170.50030.111*
C310.0932 (4)0.0628 (4)0.5148 (3)0.0933 (16)
H310.11240.07160.46740.112*
C320.1159 (3)0.1293 (3)0.5656 (2)0.0613 (10)
H320.15080.18260.55190.074*
C330.4127 (3)0.4153 (2)0.6967 (2)0.0630 (11)
H33A0.43090.39510.64940.095*
H33B0.47020.41100.72770.095*
H33C0.38990.47890.69490.095*
C340.2333 (3)0.4989 (2)0.75890 (19)0.0583 (9)
H34A0.27620.50490.80000.087*
H34B0.16630.51850.77110.087*
H34C0.25860.53720.72070.087*
C350.2137 (4)0.0448 (3)0.8764 (3)0.0828 (14)
H350.18680.05680.92150.099*
C360.1602 (4)0.0152 (3)0.8174 (3)0.0752 (13)
H360.09140.00310.81610.090*
C370.2282 (4)0.0064 (2)0.7588 (2)0.0671 (10)
H370.21230.01140.71220.080*
C380.3244 (3)0.0299 (2)0.7853 (3)0.0722 (12)
H380.38360.02920.75860.087*
C390.3175 (4)0.0540 (3)0.8570 (3)0.0835 (14)
H390.37000.07260.88680.100*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Ru0.04404 (13)0.03420 (11)0.04231 (13)0.00152 (11)0.00047 (12)0.00669 (12)
P10.0351 (4)0.0374 (4)0.0371 (4)0.0005 (4)0.0021 (3)0.0008 (3)
P20.0357 (4)0.0313 (3)0.0405 (4)0.0031 (3)0.0028 (4)0.0002 (4)
Cl0.0789 (6)0.0613 (5)0.0382 (5)0.0063 (5)0.0087 (4)0.0042 (4)
O0.0470 (13)0.0359 (11)0.0400 (12)0.0075 (10)0.0017 (10)0.0012 (9)
N0.0327 (13)0.0362 (12)0.0553 (17)0.0039 (11)0.0036 (10)0.0082 (13)
C10.0384 (18)0.0532 (19)0.050 (2)0.0054 (16)0.0008 (15)0.0029 (17)
C20.054 (2)0.074 (2)0.061 (2)0.003 (2)0.0081 (17)0.028 (2)
C30.088 (3)0.103 (4)0.078 (3)0.009 (3)0.009 (3)0.041 (3)
C40.084 (3)0.135 (5)0.091 (4)0.003 (3)0.040 (3)0.045 (3)
C50.068 (3)0.140 (5)0.103 (4)0.013 (3)0.037 (3)0.038 (4)
C60.050 (2)0.096 (3)0.075 (3)0.008 (2)0.018 (2)0.018 (2)
C70.0384 (17)0.0517 (19)0.0412 (19)0.0008 (16)0.0031 (13)0.0063 (15)
C80.046 (2)0.067 (2)0.064 (2)0.0040 (18)0.0104 (18)0.0038 (19)
C90.051 (2)0.095 (3)0.076 (3)0.008 (2)0.016 (2)0.022 (3)
C100.060 (3)0.134 (4)0.052 (3)0.000 (3)0.020 (2)0.007 (3)
C110.076 (3)0.118 (4)0.070 (3)0.003 (3)0.019 (2)0.028 (3)
C120.054 (2)0.081 (3)0.059 (2)0.008 (2)0.0132 (18)0.011 (2)
C130.0399 (15)0.0305 (13)0.0425 (16)0.0013 (14)0.0046 (14)0.0009 (12)
C140.0369 (18)0.0303 (14)0.052 (2)0.0008 (13)0.0005 (14)0.0042 (14)
C150.0465 (19)0.0397 (16)0.0444 (19)0.0077 (14)0.0115 (15)0.0096 (14)
C160.058 (2)0.0600 (19)0.049 (2)0.0104 (19)0.0006 (18)0.0144 (16)
C170.084 (3)0.088 (3)0.050 (2)0.023 (3)0.004 (2)0.011 (2)
C180.106 (4)0.086 (3)0.061 (3)0.034 (3)0.018 (3)0.029 (2)
C190.105 (4)0.053 (2)0.080 (3)0.022 (2)0.038 (3)0.031 (2)
C200.071 (3)0.0451 (19)0.067 (3)0.0086 (19)0.028 (2)0.0124 (18)
C210.0391 (18)0.0305 (15)0.069 (2)0.0030 (14)0.0075 (16)0.0042 (15)
C220.050 (2)0.052 (2)0.083 (3)0.0025 (18)0.0043 (19)0.0019 (19)
C230.044 (2)0.059 (2)0.121 (4)0.0018 (18)0.007 (2)0.003 (2)
C240.047 (3)0.054 (2)0.135 (5)0.0059 (18)0.021 (3)0.001 (2)
C250.067 (3)0.067 (2)0.094 (3)0.006 (2)0.033 (2)0.003 (2)
C260.048 (2)0.052 (2)0.073 (3)0.0006 (16)0.0191 (19)0.0017 (19)
C270.0362 (18)0.0409 (17)0.054 (2)0.0020 (14)0.0040 (15)0.0044 (15)
C280.055 (2)0.048 (2)0.076 (3)0.0089 (17)0.0082 (19)0.0005 (19)
C290.064 (3)0.051 (2)0.111 (4)0.014 (2)0.012 (3)0.021 (2)
C300.102 (4)0.083 (3)0.093 (4)0.013 (3)0.000 (3)0.047 (3)
C310.090 (3)0.106 (4)0.084 (3)0.031 (3)0.017 (3)0.052 (3)
C320.063 (2)0.065 (2)0.056 (2)0.0117 (19)0.0045 (18)0.0172 (19)
C330.046 (2)0.055 (2)0.089 (3)0.0103 (16)0.002 (2)0.019 (2)
C340.075 (2)0.0404 (16)0.059 (2)0.0039 (19)0.007 (2)0.0078 (15)
C350.124 (5)0.054 (2)0.070 (3)0.011 (3)0.007 (3)0.036 (2)
C360.074 (3)0.044 (2)0.108 (4)0.007 (2)0.001 (3)0.026 (2)
C370.077 (3)0.0311 (16)0.093 (3)0.001 (2)0.010 (3)0.0051 (17)
C380.063 (3)0.0441 (19)0.110 (4)0.0105 (18)0.008 (3)0.018 (2)
C390.087 (3)0.062 (3)0.101 (4)0.004 (2)0.031 (3)0.039 (3)
Geometric parameters (Å, º) top
Ru—C382.171 (4)C16—H160.9300
Ru—C372.186 (3)C17—C181.363 (6)
Ru—C392.213 (4)C17—H170.9300
Ru—C352.235 (4)C18—C191.363 (6)
Ru—C362.235 (4)C18—H180.9300
Ru—P22.2675 (8)C19—C201.414 (5)
Ru—P12.2906 (8)C19—H190.9300
Ru—Cl2.4382 (9)C20—H200.9300
P1—N1.684 (2)C21—C261.378 (5)
P1—C11.838 (3)C21—C221.391 (5)
P1—C71.838 (3)C22—C231.380 (5)
P2—O1.631 (2)C22—H220.9300
P2—C211.836 (3)C23—C241.380 (6)
P2—C271.837 (3)C23—H230.9300
O—C141.445 (3)C24—C251.361 (6)
N—C331.457 (4)C24—H240.9300
N—C131.471 (4)C25—C261.403 (5)
C1—C61.381 (5)C25—H250.9300
C1—C21.394 (5)C26—H260.9300
C2—C31.386 (5)C27—C321.380 (5)
C2—H20.9300C27—C281.393 (5)
C3—C41.372 (6)C28—C291.392 (5)
C3—H30.9300C28—H280.9300
C4—C51.347 (7)C29—C301.372 (6)
C4—H40.9300C29—H290.9300
C5—C61.385 (5)C30—C311.378 (6)
C5—H50.9300C30—H300.9300
C6—H60.9300C31—C321.377 (5)
C7—C81.385 (5)C31—H310.9300
C7—C121.386 (5)C32—H320.9300
C8—C91.389 (5)C33—H33A0.9600
C8—H80.9300C33—H33B0.9600
C9—C101.356 (6)C33—H33C0.9600
C9—H90.9300C34—H34A0.9600
C10—C111.388 (6)C34—H34B0.9600
C10—H100.9300C34—H34C0.9600
C11—C121.382 (5)C35—C361.377 (6)
C11—H110.9300C35—C391.430 (6)
C12—H120.9300C35—H350.9300
C13—C141.539 (4)C36—C371.425 (6)
C13—C341.540 (4)C36—H360.9300
C13—H130.9800C37—C381.410 (5)
C14—C151.508 (4)C37—H370.9300
C14—H140.9800C38—C391.387 (6)
C15—C161.376 (5)C38—H380.9300
C15—C201.391 (4)C39—H390.9300
C16—C171.393 (5)
C38—Ru—C3737.76 (15)C20—C15—C14119.8 (3)
C38—Ru—C3936.88 (17)C15—C16—C17121.5 (4)
C37—Ru—C3962.67 (17)C15—C16—H16119.2
C38—Ru—C3561.65 (18)C17—C16—H16119.2
C37—Ru—C3561.83 (17)C18—C17—C16119.6 (4)
C39—Ru—C3537.51 (16)C18—C17—H17120.2
C38—Ru—C3662.05 (16)C16—C17—H17120.2
C37—Ru—C3637.59 (15)C17—C18—C19120.7 (4)
C39—Ru—C3661.81 (16)C17—C18—H18119.7
C35—Ru—C3635.90 (15)C19—C18—H18119.7
C38—Ru—P2126.79 (14)C18—C19—C20120.1 (4)
C37—Ru—P296.31 (12)C18—C19—H19120.0
C39—Ru—P2158.67 (13)C20—C19—H19120.0
C35—Ru—P2130.98 (15)C15—C20—C19119.6 (4)
C36—Ru—P299.71 (12)C15—C20—H20120.2
C38—Ru—P191.46 (11)C19—C20—H20120.2
C37—Ru—P1117.90 (13)C26—C21—C22118.4 (3)
C39—Ru—P1100.03 (13)C26—C21—P2121.9 (3)
C35—Ru—P1135.88 (15)C22—C21—P2119.6 (3)
C36—Ru—P1153.20 (13)C23—C22—C21121.3 (4)
P2—Ru—P193.01 (3)C23—C22—H22119.3
C38—Ru—Cl135.41 (15)C21—C22—H22119.3
C37—Ru—Cl147.36 (12)C22—C23—C24119.5 (4)
C39—Ru—Cl99.09 (16)C22—C23—H23120.2
C35—Ru—Cl87.00 (13)C24—C23—H23120.2
C36—Ru—Cl110.64 (14)C25—C24—C23120.2 (4)
P2—Ru—Cl97.53 (3)C25—C24—H24119.9
P1—Ru—Cl90.73 (3)C23—C24—H24119.9
N—P1—C1103.47 (14)C24—C25—C26120.3 (4)
N—P1—C7104.60 (14)C24—C25—H25119.8
C1—P1—C7102.41 (15)C26—C25—H25119.8
N—P1—Ru119.63 (9)C21—C26—C25120.2 (4)
C1—P1—Ru115.00 (12)C21—C26—H26119.9
C7—P1—Ru109.91 (10)C25—C26—H26119.9
O—P2—C21102.49 (13)C32—C27—C28118.2 (3)
O—P2—C2795.05 (13)C32—C27—P2123.2 (3)
C21—P2—C2798.08 (14)C28—C27—P2118.6 (3)
O—P2—Ru120.45 (8)C29—C28—C27120.6 (4)
C21—P2—Ru120.29 (12)C29—C28—H28119.7
C27—P2—Ru115.60 (10)C27—C28—H28119.7
C14—O—P2125.41 (19)C30—C29—C28119.7 (4)
C33—N—C13119.2 (2)C30—C29—H29120.2
C33—N—P1120.0 (2)C28—C29—H29120.2
C13—N—P1120.74 (18)C29—C30—C31120.3 (4)
C6—C1—C2117.4 (3)C29—C30—H30119.9
C6—C1—P1124.5 (3)C31—C30—H30119.9
C2—C1—P1118.0 (3)C32—C31—C30119.8 (4)
C3—C2—C1120.6 (4)C32—C31—H31120.1
C3—C2—H2119.7C30—C31—H31120.1
C1—C2—H2119.7C31—C32—C27121.4 (4)
C4—C3—C2120.3 (4)C31—C32—H32119.3
C4—C3—H3119.8C27—C32—H32119.3
C2—C3—H3119.8N—C33—H33A109.5
C5—C4—C3119.8 (4)N—C33—H33B109.5
C5—C4—H4120.1H33A—C33—H33B109.5
C3—C4—H4120.1N—C33—H33C109.5
C4—C5—C6120.6 (4)H33A—C33—H33C109.5
C4—C5—H5119.7H33B—C33—H33C109.5
C6—C5—H5119.7C13—C34—H34A109.5
C1—C6—C5121.3 (4)C13—C34—H34B109.5
C1—C6—H6119.3H34A—C34—H34B109.5
C5—C6—H6119.3C13—C34—H34C109.5
C8—C7—C12118.6 (3)H34A—C34—H34C109.5
C8—C7—P1121.5 (3)H34B—C34—H34C109.5
C12—C7—P1119.5 (3)C36—C35—C39108.9 (5)
C7—C8—C9121.0 (4)C36—C35—Ru72.1 (2)
C7—C8—H8119.5C39—C35—Ru70.4 (2)
C9—C8—H8119.5C36—C35—H35125.6
C10—C9—C8120.3 (4)C39—C35—H35125.6
C10—C9—H9119.9Ru—C35—H35123.6
C8—C9—H9119.9C35—C36—C37108.3 (4)
C9—C10—C11119.3 (4)C35—C36—Ru72.0 (2)
C9—C10—H10120.3C37—C36—Ru69.3 (2)
C11—C10—H10120.3C35—C36—H36125.9
C12—C11—C10121.0 (4)C37—C36—H36125.9
C12—C11—H11119.5Ru—C36—H36124.4
C10—C11—H11119.5C38—C37—C36106.5 (4)
C11—C12—C7119.7 (4)C38—C37—Ru70.6 (2)
C11—C12—H12120.1C36—C37—Ru73.1 (2)
C7—C12—H12120.1C38—C37—H37126.7
N—C13—C14113.6 (2)C36—C37—H37126.7
N—C13—C34113.2 (3)Ru—C37—H37121.4
C14—C13—C34110.9 (2)C39—C38—C37109.7 (4)
N—C13—H13106.2C39—C38—Ru73.2 (2)
C14—C13—H13106.2C37—C38—Ru71.7 (2)
C34—C13—H13106.2C39—C38—H38125.1
O—C14—C15105.5 (2)C37—C38—H38125.1
O—C14—C13111.0 (2)Ru—C38—H38121.6
C15—C14—C13115.5 (2)C38—C39—C35106.6 (4)
O—C14—H14108.2C38—C39—Ru69.9 (2)
C15—C14—H14108.2C35—C39—Ru72.1 (2)
C13—C14—H14108.2C38—C39—H39126.7
C16—C15—C20118.5 (3)C35—C39—H39126.7
C16—C15—C14121.7 (3)Ru—C39—H39123.0

Experimental details

Crystal data
Chemical formula[Ru(C5H5)Cl(C34H33NOP2)]
Mr735.16
Crystal system, space groupOrthorhombic, P212121
Temperature (K)296
a, b, c (Å)13.2734 (1), 14.3376 (1), 18.6640 (2)
V3)3551.92 (5)
Z4
Radiation typeMo Kα
µ (mm1)0.64
Crystal size (mm)0.30 × 0.28 × 0.14
Data collection
DiffractometerMake Model CCD area-detector
diffractometer
Absorption correctionMulti-scan
(SADABS; Sheldrick, 1996)
Tmin, Tmax0.832, 0.916
No. of measured, independent and
observed [I > 2σ(I)] reflections
25398, 9351, 6619
Rint0.044
(sin θ/λ)max1)0.703
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.038, 0.078, 1.01
No. of reflections9351
No. of parameters409
H-atom treatmentH-atom parameters constrained
Δρmax, Δρmin (e Å3)0.37, 0.59
Absolute structureFlack (1983), with 3652 Friedel pairs Query
Absolute structure parameter0.03 (2)

Computer programs: SMART (Bruker, 2001), SMART, SHELXTL (Bruker, 2001), SHELXS97 (Sheldrick, 1997), SHELXL97 (Sheldrick, 1997), SHELXTL.

Selected geometric parameters (Å, º) top
Ru—P22.2675 (8)P1—N1.684 (2)
Ru—P12.2906 (8)P2—O1.631 (2)
Ru—Cl2.4382 (9)
C38—Ru—P2126.79 (14)C38—Ru—Cl135.41 (15)
C38—Ru—P191.46 (11)P2—Ru—Cl97.53 (3)
P2—Ru—P193.01 (3)P1—Ru—Cl90.73 (3)
 

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