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Acta Crystallogr Sect E Struct Rep Online. 2009 November 1; 65(Pt 11): m1321–m1322.
Published online 2009 October 7. doi:  10.1107/S1600536809039816
PMCID: PMC2971050

Carbon­yl[4-(2,3-dimethyl­phenyl­amino)pent-3-en-2-onato-κ2 N,O](triphenyl­phosphine-κP)rhodium(I)

Abstract

In the title compound, [Rh(C13H16NO)(C18H15P)(CO)], the coordination geometry of the RhI atom is square-planar, formed by the coordinating N and O atoms of the bidentate enaminoketonate ligand, one C atom from the carbonyl group and a P atom from triphenyl­phosphine. The complex displays a 0.591 (3):0.409 (3) ratio disorder of the phenyl unit of the monoanionic N,O-bidentate ligand. Intra­molecular hydrogen bonding is observed between a C—H group of the triphenyl­phosphine unit and the O atom of the enamino­ketonate ligand.

Related literature

For related derivatives of the 4-phenyl­amino­pent-3-en-2-onate ligand, see: Da Silva et al. (1993 [triangle]); Gordon et al. (2002 [triangle]); Shaheen et al. (2006 [triangle]). For related dicarbonyl rhodium(I) complexes with a bidentate ligand, see: Cornils & Herrmann (1996 [triangle]); Trzeciak & Ziółkowski (1994 [triangle]); van Rooy et al. (1995 [triangle]). For related carbonyl rhodium(I) complexes with a phosphine and a bidentate ligand, see: Bonati & Wilkinson (1964 [triangle]); Damoense et al. (1994 [triangle]); Lamprecht et al. (1997 [triangle]); Leipoldt et al. (1978 [triangle]); Purcell et al. (1995 [triangle]); Varshavsky et al. (2001 [triangle]). For background information, see: Tolman (1977 [triangle]).

An external file that holds a picture, illustration, etc.
Object name is e-65-m1321-scheme1.jpg

Experimental

Crystal data

  • [Rh(C13H16NO)(C18H15P)(CO)]
  • M r = 595.46
  • Monoclinic, An external file that holds a picture, illustration, etc.
Object name is e-65-m1321-efi1.jpg
  • a = 14.9077 (3) Å
  • b = 11.6202 (3) Å
  • c = 16.0256 (4) Å
  • β = 93.521 (1)°
  • V = 2770.88 (11) Å3
  • Z = 4
  • Mo Kα radiation
  • μ = 0.70 mm−1
  • T = 100 K
  • 0.25 × 0.15 × 0.13 mm

Data collection

  • Bruker X8 APEXII 4K Kappa CCD diffractometer
  • Absorption correction: multi-scan (SADABS; Bruker, 2001 [triangle]) T min = 0.844, T max = 0.914
  • 30367 measured reflections
  • 6985 independent reflections
  • 5783 reflections with I > 2σ(I)
  • R int = 0.040

Refinement

  • R[F 2 > 2σ(F 2)] = 0.033
  • wR(F 2) = 0.076
  • S = 1.04
  • 6985 reflections
  • 305 parameters
  • H-atom parameters constrained
  • Δρmax = 0.60 e Å−3
  • Δρmin = −0.69 e Å−3

Data collection: APEX2 (Bruker, 2007 [triangle]); cell refinement: SAINT-Plus (Bruker, 2007 [triangle]); data reduction: SAINT-Plus; program(s) used to solve structure: SIR92 (Altomare et al., 1994 [triangle]); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 [triangle]); molecular graphics: DIAMOND (Brandenburg & Putz, 1999 [triangle]); software used to prepare material for publication: WinGX (Farrugia, 1999 [triangle]).

Table 1
Hydrogen-bond geometry (Å, °)
Table 2
Comparative geometrical parameters for similar [Rh(N,O-bid)(CO)(PPh3)] complexes (Å,°)

Supplementary Material

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536809039816/hy2218sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809039816/hy2218Isup2.hkl

Additional supplementary materials: crystallographic information; 3D view; checkCIF report

Acknowledgments

Financial assistance from the University of the Free State is gratefully acknowledged, while Mr Leo Kirsten is thanked for the XRD data collections. We also express our gratitude towards SASOL and the South African National Research Foundation (SA-NRF/THRIP) for financial support of this project. Part of this material is based on work supported by the SA-NRF/THRIP under grant No. GUN 2068915. Opinions, findings, conclusions or recommendations expressed in this material are those of the authors and do not necessarily reflect the views of the SA-NRF.

supplementary crystallographic information

Comment

Rhodium(I) dicarbonyl complexes of the type [Rh(L,L')(CO)2] containing chelating mono-anionic bidentate (L,L') ligands coordinated to rhodium via (O,O) donor atoms have been studied as catalyst precursors (Cornils & Herrmann, 1996; Trzeciak & Ziółkowski, 1994; van Rooy et al., 1995). In this study the investigation of these β-diketonato complexes is followed by complexes containing bidentate β-enaminoketonato ligands such as 4-(phenylamino)pent-3-en-2-onato (Phony) (Shaheen et al., 2006) coordinated to rhodium via (N,O) donor atoms. Dicarbonyl complexes of the [Rh(N,O-bid)(CO)2]-type (Varshavsky et al., 2001) react with phosphorus ligands to form [Rh(N,O-bid)(CO)(PZ3)] complexes (Damoense et al., 1994; Varshavsky et al., 2001). According to Bonati & Wilkinson (1964), only one CO group will be substituted by triphenylphosphine, with the product being one of two possible isomers. Since N atom has a larger trans-influence than O atom, the CO group trans to the N atom will be substituted. This is evident in the title compound (Fig. 1), where [Rh(2,3-diMe-Phony)(CO)(PPh3)] is formed by the substitution of the carbonyl ligand in the dicarbonyl rhodium(I) complex [Rh(2,3-diMe-Phony)(CO)2] by PPh3.

Bond distances involving Rh atom in the title complex differ significantly from the distances in related complexes (Table 2). The Rh—N bond distance in the title complex is longer than those in similar complexes while the Rh—O bond distance is shorter. This is due to the steric influence of the phenyl group connected to N atom in the title compound, as opposed to H atom in the related complexes. The Rh—C and the carbonyl C—O bond distances do not differ substantially from the distances in the related complexes (Table 2). The N—Rh—O bite angle is slightly larger than those observed in similar complexes found in literature. The effective cone angle, θE (Tolman, 1977), of 156.39 (3)° is similar to the angles in the related compounds. The title complex displays a disorder of the phenyl ring in a 59:41% ratio.

Experimental

To a 5 ml acetone solution of [Rh(2,3-diMe-Phony)(CO)2] (0.0204 g, 56.48 mmol) was added PPh3 (0.0151 g, 57.57 mmol) resulting in the immediate evolution of gas. Crystallization from acetone produced yellow crystals in quantitative yield (0.0334 g). IR (KBr): νCO 1966.93 s (cm-1).

Refinement

The methyl and aromatic H atoms were placed in geometrically idealized positions and constrained to ride on their parent atoms, with C—H = 0.98 and 0.95 Å and Uiso(H) = 1.5Ueq(C) and 1.2Ueq(C), respectively. The methyl groups were generated to fit the difference electron density and the groups were then refined as rigid rotors.

Figures

Fig. 1.
Molecular structure of the title compound. Displacement ellipsoids are drawn at the 50% probability level. H atoms have been omitted for clarity.
Fig. 2.
Crystal packing of the title compound.

Crystal data

[Rh(C13H16NO)(C18H15P)(CO)]F(000) = 1224
Mr = 595.46Dx = 1.427 Mg m3
Monoclinic, P21/cMo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybcCell parameters from 8984 reflections
a = 14.9077 (3) Åθ = 2.2–28.4°
b = 11.6202 (3) ŵ = 0.70 mm1
c = 16.0256 (4) ÅT = 100 K
β = 93.521 (1)°Cuboid, yellow
V = 2770.88 (11) Å30.25 × 0.15 × 0.13 mm
Z = 4

Data collection

Bruker X8 APEXII 4K Kappa CCD diffractometer6985 independent reflections
Radiation source: fine-focus sealed tube5783 reflections with I > 2σ(I)
graphiteRint = 0.040
ω and [var phi] scansθmax = 28.5°, θmin = 1.4°
Absorption correction: multi-scan (SADABS; Bruker, 2001)h = −19→19
Tmin = 0.844, Tmax = 0.914k = −15→14
30367 measured reflectionsl = −21→18

Refinement

Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.033Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.076H-atom parameters constrained
S = 1.04w = 1/[σ2(Fo2) + (0.0235P)2 + 2.8578P] where P = (Fo2 + 2Fc2)/3
6985 reflections(Δ/σ)max = 0.005
305 parametersΔρmax = 0.60 e Å3
0 restraintsΔρmin = −0.69 e Å3

Special details

Experimental. The intensity data was collected on a Bruker X8 APEXII 4 K Kappa CCD diffractometer using an exposure time of 60 s/frame. A total of 1033 frames were collected with a frame width of 0.5° covering up to θ = 28.41° with 99.4% completeness accomplished.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2)

xyzUiso*/UeqOcc. (<1)
Rh10.258727 (11)0.605541 (15)1.062396 (10)0.01882 (6)
N110.26580 (15)0.43296 (18)1.03172 (15)0.0361 (5)
O120.36554 (10)0.63702 (14)0.99328 (9)0.0221 (3)
O140.09801 (11)0.57318 (15)1.15945 (10)0.0285 (4)
P130.26175 (4)0.79721 (5)1.08760 (3)0.01818 (12)
C10.3204 (2)0.2591 (2)0.9641 (2)0.0576 (10)
H1A0.30990.2181.01610.086*
H1B0.37820.23520.94390.086*
H1C0.27220.24090.92190.086*
C20.32179 (18)0.3869 (2)0.98045 (17)0.0325 (6)
C30.38454 (16)0.4508 (2)0.93713 (15)0.0267 (5)
H30.41760.40930.89820.032*
C40.40317 (14)0.5655 (2)0.94473 (14)0.0222 (5)
C50.47221 (16)0.6203 (2)0.89254 (16)0.0318 (6)
H5A0.44190.66840.84920.048*
H5B0.50680.56010.86620.048*
H5C0.51290.6680.92830.048*
C11A0.22412 (17)0.3512 (2)1.08695 (16)0.0249 (5)0.591 (3)
C12A0.13769 (16)0.3169 (2)1.06046 (13)0.0249 (5)0.591 (3)
C13A0.09120 (13)0.2400 (2)1.10833 (15)0.0249 (5)0.591 (3)
C14A0.13113 (16)0.1974 (2)1.18269 (14)0.0249 (5)0.591 (3)
H14A0.09940.14491.21540.03*0.591 (3)
C15A0.21756 (17)0.2318 (2)1.20919 (14)0.0249 (5)0.591 (3)
H15A0.24490.20271.260.03*0.591 (3)
C16A0.26405 (14)0.3086 (3)1.16132 (17)0.0249 (5)0.591 (3)
H16A0.32310.33211.17940.03*0.591 (3)
C18A−0.0011 (3)0.1950 (4)1.0797 (2)0.0249 (5)0.591 (3)
H18A0.00430.14231.03250.037*0.591 (3)
H18B−0.04010.25961.06220.037*0.591 (3)
H18C−0.02710.15391.12580.037*0.591 (3)
C17A0.0953 (3)0.3664 (4)0.9799 (3)0.0249 (5)0.591 (3)
H17A0.09020.45010.98530.037*0.591 (3)
H17B0.03540.3330.96880.037*0.591 (3)
H17C0.13290.3480.93370.037*0.591 (3)
C11B0.1803 (2)0.3671 (3)1.0474 (2)0.0243 (7)0.409 (3)
C12B0.18861 (19)0.3040 (3)1.1212 (2)0.0243 (7)0.409 (3)
C13B0.1158 (2)0.2418 (3)1.14741 (19)0.0243 (7)0.409 (3)
C14B0.0346 (2)0.2428 (3)1.0998 (2)0.0243 (7)0.409 (3)
H14B−0.01520.20031.11780.029*0.409 (3)
C15B0.0263 (2)0.3059 (3)1.0261 (2)0.0243 (7)0.409 (3)
H15B−0.02920.30650.99360.029*0.409 (3)
C16B0.0991 (3)0.3680 (3)0.99988 (19)0.0243 (7)0.409 (3)
H16B0.09340.41110.94950.029*0.409 (3)
C17B0.2760 (4)0.3064 (6)1.1737 (4)0.0243 (7)0.409 (3)
H17D0.30930.23511.1650.036*0.409 (3)
H17E0.26360.31321.23280.036*0.409 (3)
H17F0.31190.37241.15740.036*0.409 (3)
C18B0.1219 (4)0.1738 (5)1.2287 (3)0.0243 (7)0.409 (3)
H18D0.06240.1441.23990.036*0.409 (3)
H18E0.14360.22411.27470.036*0.409 (3)
H18F0.16380.10941.22380.036*0.409 (3)
C140.16135 (15)0.58652 (19)1.12283 (14)0.0215 (5)
C3110.19823 (15)0.8522 (2)1.17253 (14)0.0212 (5)
C3120.23991 (16)0.8923 (2)1.24725 (15)0.0261 (5)
H3120.30360.8981.25310.031*
C3130.18891 (18)0.9239 (2)1.31310 (16)0.0336 (6)
H3130.21770.95011.36420.04*
C3140.09599 (18)0.9173 (2)1.30437 (17)0.0372 (6)
H3140.06110.93951.34930.045*
C3150.05421 (17)0.8787 (2)1.23056 (18)0.0364 (6)
H315−0.00950.87451.22480.044*
C3160.10419 (16)0.8460 (2)1.16490 (16)0.0289 (5)
H3160.07480.81921.11430.035*
C3210.22426 (16)0.8831 (2)0.99645 (14)0.0239 (5)
C3220.17703 (18)0.9858 (2)1.00150 (15)0.0329 (6)
H3220.16151.0141.05440.04*
C3230.1525 (2)1.0472 (2)0.92915 (17)0.0409 (7)
H3230.11941.11670.93290.049*
C3240.1756 (2)1.0084 (2)0.85193 (16)0.0383 (6)
H3240.15911.05110.80280.046*
C3250.22301 (19)0.9068 (2)0.84678 (16)0.0362 (6)
H3250.23930.87960.79390.043*
C3260.24695 (16)0.8442 (2)0.91864 (14)0.0280 (5)
H3260.27910.77410.91440.034*
C3310.37540 (15)0.8504 (2)1.11391 (13)0.0224 (5)
C3320.40227 (19)0.9603 (2)1.09345 (18)0.0389 (7)
H3320.36231.00961.06180.047*
C3330.4886 (2)0.9988 (3)1.1196 (2)0.0510 (8)
H3330.50731.0741.10530.061*
C3340.54615 (18)0.9282 (3)1.16566 (18)0.0431 (8)
H3340.60430.9551.18390.052*
C3350.52026 (16)0.8193 (3)1.18548 (16)0.0353 (6)
H3350.56050.77051.21720.042*
C3360.43533 (15)0.7797 (2)1.15942 (14)0.0264 (5)
H3360.41810.70351.17290.032*

Atomic displacement parameters (Å2)

U11U22U33U12U13U23
Rh10.01877 (9)0.01664 (9)0.02180 (9)−0.00199 (7)0.00727 (6)−0.00079 (7)
N110.0465 (13)0.0177 (10)0.0478 (13)−0.0072 (9)0.0327 (11)−0.0047 (9)
O120.0197 (8)0.0216 (8)0.0256 (8)0.0005 (6)0.0075 (6)0.0035 (6)
O140.0241 (9)0.0315 (10)0.0309 (9)−0.0077 (7)0.0108 (7)−0.0045 (7)
P130.0172 (3)0.0182 (3)0.0191 (3)−0.0007 (2)0.0002 (2)−0.0006 (2)
C10.083 (2)0.0238 (15)0.073 (2)−0.0050 (15)0.055 (2)−0.0111 (15)
C20.0384 (14)0.0220 (13)0.0393 (14)−0.0005 (11)0.0201 (12)−0.0043 (11)
C30.0271 (12)0.0248 (13)0.0297 (12)0.0038 (10)0.0134 (10)−0.0004 (10)
C40.0169 (10)0.0277 (12)0.0223 (11)0.0033 (9)0.0038 (9)0.0054 (9)
C50.0247 (12)0.0372 (15)0.0349 (13)−0.0004 (11)0.0128 (10)0.0068 (11)
C11A0.0258 (8)0.0232 (8)0.0259 (8)−0.0024 (6)0.0018 (6)0.0011 (6)
C12A0.0258 (8)0.0232 (8)0.0259 (8)−0.0024 (6)0.0018 (6)0.0011 (6)
C13A0.0258 (8)0.0232 (8)0.0259 (8)−0.0024 (6)0.0018 (6)0.0011 (6)
C14A0.0258 (8)0.0232 (8)0.0259 (8)−0.0024 (6)0.0018 (6)0.0011 (6)
C15A0.0258 (8)0.0232 (8)0.0259 (8)−0.0024 (6)0.0018 (6)0.0011 (6)
C16A0.0258 (8)0.0232 (8)0.0259 (8)−0.0024 (6)0.0018 (6)0.0011 (6)
C18A0.0258 (8)0.0232 (8)0.0259 (8)−0.0024 (6)0.0018 (6)0.0011 (6)
C17A0.0258 (8)0.0232 (8)0.0259 (8)−0.0024 (6)0.0018 (6)0.0011 (6)
C11B0.0281 (12)0.0204 (11)0.0246 (11)0.0016 (9)0.0036 (9)0.0003 (8)
C12B0.0281 (12)0.0204 (11)0.0246 (11)0.0016 (9)0.0036 (9)0.0003 (8)
C13B0.0281 (12)0.0204 (11)0.0246 (11)0.0016 (9)0.0036 (9)0.0003 (8)
C14B0.0281 (12)0.0204 (11)0.0246 (11)0.0016 (9)0.0036 (9)0.0003 (8)
C15B0.0281 (12)0.0204 (11)0.0246 (11)0.0016 (9)0.0036 (9)0.0003 (8)
C16B0.0281 (12)0.0204 (11)0.0246 (11)0.0016 (9)0.0036 (9)0.0003 (8)
C17B0.0281 (12)0.0204 (11)0.0246 (11)0.0016 (9)0.0036 (9)0.0003 (8)
C18B0.0281 (12)0.0204 (11)0.0246 (11)0.0016 (9)0.0036 (9)0.0003 (8)
C140.0238 (11)0.0192 (12)0.0216 (11)−0.0045 (9)0.0027 (9)−0.0031 (9)
C3110.0201 (11)0.0193 (11)0.0242 (11)0.0002 (9)0.0009 (9)−0.0020 (9)
C3120.0232 (12)0.0279 (13)0.0267 (12)0.0035 (10)−0.0017 (9)−0.0048 (10)
C3130.0363 (14)0.0400 (16)0.0242 (12)0.0017 (12)−0.0009 (11)−0.0116 (11)
C3140.0320 (14)0.0462 (17)0.0345 (14)0.0044 (12)0.0106 (11)−0.0135 (12)
C3150.0201 (12)0.0439 (17)0.0459 (16)−0.0004 (11)0.0072 (11)−0.0112 (13)
C3160.0235 (12)0.0312 (14)0.0319 (13)−0.0013 (10)0.0007 (10)−0.0085 (11)
C3210.0280 (12)0.0199 (12)0.0231 (11)−0.0001 (10)−0.0034 (9)−0.0003 (9)
C3220.0483 (16)0.0230 (13)0.0267 (12)0.0066 (12)−0.0043 (11)−0.0046 (10)
C3230.0585 (19)0.0243 (14)0.0386 (15)0.0148 (13)−0.0064 (14)0.0002 (11)
C3240.0529 (18)0.0312 (15)0.0298 (13)0.0095 (13)−0.0065 (12)0.0074 (11)
C3250.0469 (16)0.0383 (16)0.0230 (12)0.0103 (13)−0.0008 (11)0.0022 (11)
C3260.0340 (14)0.0248 (13)0.0246 (12)0.0081 (10)−0.0023 (10)0.0009 (10)
C3310.0200 (11)0.0286 (12)0.0190 (10)−0.0059 (9)0.0035 (9)−0.0027 (9)
C3320.0405 (16)0.0334 (16)0.0423 (15)−0.0137 (12)−0.0020 (13)0.0053 (12)
C3330.0503 (19)0.0486 (19)0.0550 (19)−0.0328 (16)0.0110 (15)−0.0046 (16)
C3340.0240 (13)0.067 (2)0.0387 (15)−0.0154 (14)0.0085 (12)−0.0198 (15)
C3350.0194 (12)0.0592 (19)0.0276 (12)0.0007 (12)0.0031 (10)−0.0165 (12)
C3360.0212 (11)0.0368 (14)0.0215 (11)−0.0014 (10)0.0050 (9)−0.0095 (10)

Geometric parameters (Å, °)

Rh1—C141.807 (2)C13B—C18B1.522 (6)
Rh1—O122.0280 (15)C14B—C15B1.39
Rh1—N112.069 (2)C14B—H14B0.95
Rh1—P132.2635 (6)C15B—C16B1.39
N11—C21.320 (3)C15B—H15B0.95
N11—C11A1.463 (3)C16B—H16B0.95
N11—C11B1.522 (3)C17B—H17D0.98
O12—C41.290 (3)C17B—H17E0.98
O14—C141.152 (3)C17B—H17F0.98
P13—C3111.821 (2)C18B—H18D0.98
P13—C3311.828 (2)C18B—H18E0.98
P13—C3211.828 (2)C18B—H18F0.98
C1—C21.508 (4)C311—C3121.395 (3)
C1—H1A0.98C311—C3161.401 (3)
C1—H1B0.98C312—C3131.388 (3)
C1—H1C0.98C312—H3120.95
C2—C31.410 (3)C313—C3141.386 (4)
C3—C41.366 (3)C313—H3130.95
C3—H30.95C314—C3151.378 (4)
C4—C51.507 (3)C314—H3140.95
C5—H5A0.98C315—C3161.379 (3)
C5—H5B0.98C315—H3150.95
C5—H5C0.98C316—H3160.95
C11A—C12A1.39C321—C3261.388 (3)
C11A—C16A1.39C321—C3221.390 (3)
C12A—C13A1.39C322—C3231.391 (4)
C12A—C17A1.515 (5)C322—H3220.95
C13A—C14A1.39C323—C3241.381 (4)
C13A—C18A1.516 (4)C323—H3230.95
C14A—C15A1.39C324—C3251.380 (4)
C14A—H14A0.95C324—H3240.95
C15A—C16A1.39C325—C3261.390 (3)
C15A—H15A0.95C325—H3250.95
C16A—H16A0.95C326—H3260.95
C18A—H18A0.98C331—C3321.384 (4)
C18A—H18B0.98C331—C3361.388 (3)
C18A—H18C0.98C332—C3331.403 (4)
C17A—H17A0.98C332—H3320.95
C17A—H17B0.98C333—C3341.369 (5)
C17A—H17C0.98C333—H3330.95
C11B—C12B1.39C334—C3351.366 (4)
C11B—C16B1.39C334—H3340.95
C12B—C13B1.39C335—C3361.387 (3)
C12B—C17B1.506 (7)C335—H3350.95
C13B—C14B1.39C336—H3360.95
C14—Rh1—O12176.48 (9)C14B—C15B—H15B120
C14—Rh1—N1193.62 (9)C15B—C16B—C11B120
O12—Rh1—N1189.53 (7)C15B—C16B—H16B120
C14—Rh1—P1391.86 (7)C11B—C16B—H16B120
O12—Rh1—P1384.97 (5)C12B—C17B—H17D109.5
N11—Rh1—P13174.49 (6)C12B—C17B—H17E109.5
C2—N11—C11A114.9 (2)H17D—C17B—H17E109.5
C2—N11—C11B117.8 (2)C12B—C17B—H17F109.5
C2—N11—Rh1125.77 (17)H17D—C17B—H17F109.5
C11A—N11—Rh1117.14 (17)H17E—C17B—H17F109.5
C11B—N11—Rh1113.14 (19)C13B—C18B—H18D109.5
C4—O12—Rh1126.75 (15)C13B—C18B—H18E109.5
C311—P13—C331103.07 (10)H18D—C18B—H18E109.5
C311—P13—C321104.96 (11)C13B—C18B—H18F109.5
C331—P13—C321103.48 (11)H18D—C18B—H18F109.5
C311—P13—Rh1118.23 (8)H18E—C18B—H18F109.5
C331—P13—Rh1112.44 (8)O14—C14—Rh1178.1 (2)
C321—P13—Rh1113.14 (8)C312—C311—C316118.8 (2)
C2—C1—H1A109.5C312—C311—P13122.29 (17)
C2—C1—H1B109.5C316—C311—P13118.70 (17)
H1A—C1—H1B109.5C313—C312—C311120.4 (2)
C2—C1—H1C109.5C313—C312—H312119.8
H1A—C1—H1C109.5C311—C312—H312119.8
H1B—C1—H1C109.5C314—C313—C312120.0 (2)
N11—C2—C3123.8 (2)C314—C313—H313120
N11—C2—C1120.3 (2)C312—C313—H313120
C3—C2—C1115.8 (2)C315—C314—C313120.1 (2)
C4—C3—C2127.4 (2)C315—C314—H314120
C4—C3—H3116.3C313—C314—H314120
C2—C3—H3116.3C314—C315—C316120.5 (2)
O12—C4—C3126.1 (2)C314—C315—H315119.7
O12—C4—C5113.6 (2)C316—C315—H315119.7
C3—C4—C5120.3 (2)C315—C316—C311120.2 (2)
C4—C5—H5A109.5C315—C316—H316119.9
C4—C5—H5B109.5C311—C316—H316119.9
H5A—C5—H5B109.5C326—C321—C322119.0 (2)
C4—C5—H5C109.5C326—C321—P13117.40 (18)
H5A—C5—H5C109.5C322—C321—P13123.59 (18)
H5B—C5—H5C109.5C321—C322—C323120.0 (2)
C12A—C11A—C16A120C321—C322—H322120
C12A—C11A—N11114.94 (19)C323—C322—H322120
C16A—C11A—N11125.06 (19)C324—C323—C322120.8 (2)
C11A—C12A—C13A120C324—C323—H323119.6
C11A—C12A—C17A118.8 (2)C322—C323—H323119.6
C13A—C12A—C17A121.2 (2)C325—C324—C323119.3 (2)
C12A—C13A—C14A120C325—C324—H324120.3
C12A—C13A—C18A121.9 (2)C323—C324—H324120.3
C14A—C13A—C18A118.0 (2)C324—C325—C326120.3 (2)
C15A—C14A—C13A120C324—C325—H325119.9
C15A—C14A—H14A120C326—C325—H325119.9
C13A—C14A—H14A120C321—C326—C325120.6 (2)
C14A—C15A—C16A120C321—C326—H326119.7
C14A—C15A—H15A120C325—C326—H326119.7
C16A—C15A—H15A120C332—C331—C336119.0 (2)
C15A—C16A—C11A120C332—C331—P13122.3 (2)
C15A—C16A—H16A120C336—C331—P13118.61 (18)
C11A—C16A—H16A120C331—C332—C333119.8 (3)
C12B—C11B—C16B120C331—C332—H332120.1
C12B—C11B—N11112.0 (2)C333—C332—H332120.1
C16B—C11B—N11128.0 (2)C334—C333—C332120.2 (3)
C11B—C12B—C13B120C334—C333—H333119.9
C11B—C12B—C17B119.6 (3)C332—C333—H333119.9
C13B—C12B—C17B120.4 (3)C335—C334—C333120.3 (3)
C14B—C13B—C12B120C335—C334—H334119.9
C14B—C13B—C18B118.6 (3)C333—C334—H334119.9
C12B—C13B—C18B121.4 (3)C334—C335—C336120.2 (3)
C13B—C14B—C15B120C334—C335—H335119.9
C13B—C14B—H14B120C336—C335—H335119.9
C15B—C14B—H14B120C335—C336—C331120.5 (3)
C16B—C15B—C14B120C335—C336—H336119.7
C16B—C15B—H15B120C331—C336—H336119.7
C14—Rh1—N11—C2174.7 (3)C16B—C11B—C12B—C17B−178.1 (4)
O12—Rh1—N11—C2−3.8 (3)N11—C11B—C12B—C17B−0.6 (4)
C14—Rh1—N11—C11A−23.0 (2)C11B—C12B—C13B—C14B0
O12—Rh1—N11—C11A158.5 (2)C17B—C12B—C13B—C14B178.1 (4)
C14—Rh1—N11—C11B15.6 (2)C11B—C12B—C13B—C18B−178.8 (4)
O12—Rh1—N11—C11B−162.8 (2)C17B—C12B—C13B—C18B−0.7 (5)
N11—Rh1—O12—C48.13 (19)C12B—C13B—C14B—C15B0
P13—Rh1—O12—C4−171.45 (18)C18B—C13B—C14B—C15B178.8 (4)
C14—Rh1—P13—C31116.41 (11)C13B—C14B—C15B—C16B0
O12—Rh1—P13—C311−165.13 (10)C14B—C15B—C16B—C11B0
C14—Rh1—P13—C331136.38 (11)C12B—C11B—C16B—C15B0
O12—Rh1—P13—C331−45.16 (9)N11—C11B—C16B—C15B−177.0 (4)
C14—Rh1—P13—C321−106.82 (11)C331—P13—C311—C312−16.6 (2)
O12—Rh1—P13—C32171.63 (10)C321—P13—C311—C312−124.6 (2)
C11A—N11—C2—C3−164.1 (3)Rh1—P13—C311—C312108.17 (19)
C11B—N11—C2—C3156.7 (3)C331—P13—C311—C316168.3 (2)
Rh1—N11—C2—C3−1.5 (4)C321—P13—C311—C31660.2 (2)
C11A—N11—C2—C116.8 (4)Rh1—P13—C311—C316−67.0 (2)
C11B—N11—C2—C1−22.4 (4)C316—C311—C312—C3130.9 (4)
Rh1—N11—C2—C1179.4 (2)P13—C311—C312—C313−174.3 (2)
N11—C2—C3—C45.4 (5)C311—C312—C313—C314−0.9 (4)
C1—C2—C3—C4−175.5 (3)C312—C313—C314—C3150.4 (4)
Rh1—O12—C4—C3−7.5 (3)C313—C314—C315—C3160.1 (5)
Rh1—O12—C4—C5171.45 (15)C314—C315—C316—C311−0.2 (4)
C2—C3—C4—O12−0.5 (4)C312—C311—C316—C315−0.3 (4)
C2—C3—C4—C5−179.4 (3)P13—C311—C316—C315175.1 (2)
C2—N11—C11A—C12A−98.8 (3)C311—P13—C321—C326−166.46 (19)
C11B—N11—C11A—C12A4.8 (3)C331—P13—C321—C32685.8 (2)
Rh1—N11—C11A—C12A97.0 (2)Rh1—P13—C321—C326−36.2 (2)
C2—N11—C11A—C16A81.7 (3)C311—P13—C321—C32215.4 (2)
C11B—N11—C11A—C16A−174.7 (4)C331—P13—C321—C322−92.3 (2)
Rh1—N11—C11A—C16A−82.5 (2)Rh1—P13—C321—C322145.7 (2)
C16A—C11A—C12A—C13A0C326—C321—C322—C3230.6 (4)
N11—C11A—C12A—C13A−179.5 (3)P13—C321—C322—C323178.7 (2)
C16A—C11A—C12A—C17A178.9 (3)C321—C322—C323—C324−1.0 (4)
N11—C11A—C12A—C17A−0.6 (3)C322—C323—C324—C3250.6 (5)
C11A—C12A—C13A—C14A0C323—C324—C325—C3260.2 (5)
C17A—C12A—C13A—C14A−178.9 (3)C322—C321—C326—C3250.1 (4)
C11A—C12A—C13A—C18A−176.5 (3)P13—C321—C326—C325−178.1 (2)
C17A—C12A—C13A—C18A4.6 (4)C324—C325—C326—C321−0.5 (4)
C12A—C13A—C14A—C15A0C311—P13—C331—C332−83.3 (2)
C18A—C13A—C14A—C15A176.7 (3)C321—P13—C331—C33225.9 (2)
C13A—C14A—C15A—C16A0Rh1—P13—C331—C332148.32 (19)
C14A—C15A—C16A—C11A0C311—P13—C331—C33693.63 (19)
C12A—C11A—C16A—C15A0C321—P13—C331—C336−157.22 (18)
N11—C11A—C16A—C15A179.5 (3)Rh1—P13—C331—C336−34.78 (19)
C2—N11—C11B—C12B98.0 (3)C336—C331—C332—C333−0.7 (4)
C11A—N11—C11B—C12B3.6 (3)P13—C331—C332—C333176.2 (2)
Rh1—N11—C11B—C12B−101.2 (2)C331—C332—C333—C334−0.4 (4)
C2—N11—C11B—C16B−84.8 (3)C332—C333—C334—C3350.9 (4)
C11A—N11—C11B—C16B−179.2 (5)C333—C334—C335—C336−0.3 (4)
Rh1—N11—C11B—C16B76.1 (3)C334—C335—C336—C331−0.8 (3)
C16B—C11B—C12B—C13B0C332—C331—C336—C3351.3 (3)
N11—C11B—C12B—C13B177.5 (3)P13—C331—C336—C335−175.74 (17)

Hydrogen-bond geometry (Å, °)

D—H···AD—HH···AD···AD—H···A
C326—H326···O120.952.363.177 (3)143

Table 2 Comparative geometrical parameters for similar [Rh(N,O-bid)(CO)(PPh3)] complexes (Å,°).

Parameters(I)(II)(III)
Rh1—N112.069 (2)2.045 (4)2.045 (3)
Rh1—O122.028 (2)2.044 (3)2.045 (2)
Rh1—P132.2635 (6)2.275 (1)2.281 (2)
Rh1—C141.807 (2)1.784 (5)1.804 (3)
C14—O141.152 (3)1.142 (7)1.148 (4)
N11···O122.885 (3)2.826 (6)2.841 (3)
N11—Rh1—O1289.54 (8)87.4 (1)87.95 (8)
O12—Rh1—P1384.97 (5)89.7 (1)89.91 (5)
P13—Rh1—C1491.87 (7)90.3 (2)89.48 (9)
N11—Rh1—C1493.6 (1)92.6 (2)92.6 (1)
N11—C2—C4—O124.1 (2)1.2 (4)1.5 (2)
θE (Tolman, 1977)156.39 (3)156.0 (2)156.23 (4)

(I) This work. (II) N,O-bid = 4-aminopent-3-en-2-onato (Damoense et al., 1994). (III) N,O-bid = 4-amino-1,1,1-trifluoropent-3-en-2-onato (Varshavsky et al., 2001).

Footnotes

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: HY2218).

References

  • Altomare, A., Cascarano, G., Giacovazzo, C., Guagliardi, A., Burla, M. C., Polidori, G. & Camalli, M. (1994). J. Appl. Cryst.27, 435.
  • Bonati, F. & Wilkinson, G. (1964). J. Chem. Soc. pp. 3156–3160.
  • Brandenburg, K. & Putz, H. (1999). DIAMOND Crystal Impact GbR, Bonn, Germany.
  • Bruker (2001). SADABS Bruker AXS Inc., Madison, Wisconsin, USA.
  • Bruker (2007). APEX2 and SAINT-Plus Bruker AXS Inc., Madison, Wisconsin, USA.
  • Cornils, B. & Herrmann, W. A. (1996). In Applied Homogeneous Catalysis with Organometallic Compounds: A Comprehensive Handbook Weinheim: VCH.
  • Damoense, L. J., Purcell, W., Roodt, A. & Leipoldt, J. G. (1994). Rhodium Express, 5, 10–13.
  • Da Silva, M. A. V. R., Da Silva, M. D. M. C. R., Paiva, J. P. A., Nogueira, I. M. C. S., Damas, A. M., Barkley, J. V., Harding, M. M., Akello, M. J. & Pilcher, G. (1993). J. Chem. Soc. Perkin Trans. 2, pp. 1765–1769.
  • Farrugia, L. J. (1999). J. Appl. Cryst.32, 837–838.
  • Gordon, J. C., Shukla, P., Cowley, A. H., Jones, J. N., Keogh, D. W. & Scott, B. L. (2002). Chem. Commun. pp. 2710–2711. [PubMed]
  • Lamprecht, D., Lamprecht, G. J., Botha, J. M., Umakoshi, K. & Sasaki, Y. (1997). Acta Cryst. C53, 1403–1405.
  • Leipoldt, J. G., Basson, S. S., Bok, L. D. C. & Gerber, T. I. A. (1978). Inorg. Chim. Acta, 26, L35–L37.
  • Purcell, W., Basson, S. S., Leipoldt, J. G., Roodt, A. & Preston, H. (1995). Inorg. Chim. Acta, 234, 153–156.
  • Rooy, A. van, Orij, E. N., Kamer, P. C. J. & van Leeuwen, P. W. M. N. (1995). Organometallics, 14, 34–43.
  • Shaheen, F., Marchio, L., Badshah, A. & Khosa, M. K. (2006). Acta Cryst. E62, o873–o874.
  • Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. [PubMed]
  • Tolman, C. A. (1977). Chem. Rev.77, 313–348.
  • Trzeciak, A. M. & Ziółkowski, J. J. (1994). J. Organomet. Chem.464, 107–111.
  • Varshavsky, Y. S., Galding, M. R., Cherkasova, T. G., Podkorytov, I. S., Nikol’skii, A. B., Trzeciak, A. M., Olejnik, Z., Lis, T. & Ziółkowski, J. J. (2001). J. Organomet. Chem.628, 195–210.

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