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The crystal structure of the title compound, [Rh(C5H7O2)(C10H19P)(CO)], consists of discrete chiral mol­ecules. The square-planar coordination geometry around RhI involves two O atoms of one acetyl­acetonate ligand, one carbonyl group and one P atom of a monodentate di­allyl­phosphine. The double bonds of the allyl groups have a mutual π–π interaction.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536803015691/cf6271sup1.cif
Contains datablocks global, I

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536803015691/cf6271Isup2.hkl
Contains datablock I

CCDC reference: 221644

Key indicators

  • Single-crystal X-ray study
  • T = 293 K
  • Mean [sigma](C-C) = 0.006 Å
  • R factor = 0.022
  • wR factor = 0.049
  • Data-to-parameter ratio = 14.7

checkCIF results

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Red Alert Alert Level A:
PUBL_003 Alert A The contact author's name is missing, _publ_contact_author_name. ADDSYM reports no extra symmetry General Notes
REFLT_03 From the CIF: _diffrn_reflns_theta_max 24.98 From the CIF: _reflns_number_total 2795 Count of symmetry unique reflns 1889 Completeness (_total/calc) 147.96% TEST3: Check Friedels for noncentro structure Estimate of Friedel pairs measured 906 Fraction of Friedel pairs measured 0.480 Are heavy atom types Z>Si present yes WARNING: Large fraction of Friedel related reflns may be needed to determine absolute structure
1 Alert Level A = Potentially serious problem
0 Alert Level B = Potential problem
0 Alert Level C = Please check

Computing details top

Data collection: MSC/AFC Diffractometer Control Software (Molecular Structure Corporation, 1991); cell refinement: MSC/AFC Diffractometer Control Software; data reduction: TEXSAN (Molecular Structure Corporation, 1999); program(s) used to solve structure: SHELXTL-NT (Bruker, 1998); program(s) used to refine structure: SHELXTL-NT; molecular graphics: SHELXTL-NT; software used to prepare material for publication: SHELXTL-NT.

(I) top
Crystal data top
[Rh(C5H7O2)(C10H19P)(CO)]Dx = 1.419 Mg m3
Mr = 400.25Mo Kα radiation, λ = 0.71073 Å
Orthorhombic, P212121Cell parameters from 25 reflections
a = 11.970 (2) Åθ = 26.4–31.7°
b = 12.270 (3) ŵ = 1.00 mm1
c = 12.758 (3) ÅT = 293 K
V = 1873.7 (7) Å3Prism, yellow
Z = 40.36 × 0.30 × 0.15 mm
F(000) = 824
Data collection top
Rigaku AFC-7S
diffractometer
2580 reflections with I > 2σ(I)
Radiation source: Normal-focus sealed tubeRint = 0.013
Graphite monochromatorθmax = 25.0°, θmin = 2.3°
ω–2θ scansh = 1014
Absorption correction: ψ scan
(North et al., 1968)
k = 014
Tmin = 0.766, Tmax = 0.860l = 115
3098 measured reflections3 standard reflections every 150 reflections
2795 independent reflections intensity decay: none
Refinement top
Refinement on F2Secondary atom site location: difference Fourier map
Least-squares matrix: fullHydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.022H-atom parameters constrained
wR(F2) = 0.049 w = 1/[σ2(Fo2) + (0.0248P)2 + 0.2043P]
where P = (Fo2 + 2Fc2)/3
S = 1.05(Δ/σ)max = 0.001
2795 reflectionsΔρmax = 0.25 e Å3
190 parametersΔρmin = 0.21 e Å3
0 restraintsAbsolute structure: Flack (1983), 956 Friedel pairs
Primary atom site location: structure-invariant direct methodsAbsolute structure parameter: 0.05 (3)
Special details top

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
Rh10.91546 (2)0.964193 (18)0.12852 (2)0.04217 (8)
P11.05392 (6)0.84271 (6)0.14477 (7)0.04182 (19)
O10.8260 (2)0.87419 (19)0.2330 (2)0.0571 (6)
O20.78003 (18)1.07020 (15)0.1194 (2)0.0537 (6)
O31.0552 (3)1.0884 (3)0.0182 (3)0.0970 (11)
C10.7300 (3)0.8948 (3)0.2710 (3)0.0526 (8)
C20.6643 (3)0.9823 (3)0.2434 (3)0.0577 (9)
H2A0.59550.98800.27670.069*
C30.6899 (3)1.0634 (3)0.1706 (3)0.0515 (9)
C40.6065 (3)1.1523 (3)0.1506 (4)0.0850 (15)
H4A0.63601.20210.09960.127*
H4B0.59171.19060.21470.127*
H4C0.53841.12100.12460.127*
C50.6914 (4)0.8173 (3)0.3532 (4)0.0806 (13)
H5A0.74680.76170.36320.121*
H5B0.62240.78430.33160.121*
H5C0.68010.85580.41780.121*
C61.0000 (3)1.0407 (3)0.0384 (3)0.0594 (9)
C71.1974 (3)0.8907 (3)0.1247 (4)0.0574 (8)
H7A1.24820.83160.14150.069*
H7B1.20710.90760.05090.069*
C81.2304 (4)0.9883 (3)0.1872 (4)0.0720 (11)
H8A1.18431.04920.18340.086*
C91.3161 (5)0.9950 (5)0.2452 (5)0.113 (2)
H9A1.36430.93600.25120.136*
H9B1.33071.05910.28170.136*
C101.0552 (3)0.7796 (3)0.2744 (3)0.0580 (10)
H10A0.98910.73450.28130.070*
H10B1.11970.73210.27910.070*
C111.0584 (3)0.8571 (3)0.3640 (3)0.0640 (10)
H11A1.00160.90860.36760.077*
C121.1315 (4)0.8593 (4)0.4361 (4)0.0859 (14)
H12A1.18990.80930.43570.103*
H12B1.12670.91100.48930.103*
C131.0429 (3)0.7248 (3)0.0526 (3)0.0538 (9)
C141.0500 (5)0.7693 (4)0.0597 (3)0.0863 (16)
H14A1.04420.71010.10860.129*
H14B1.12010.80590.06930.129*
H14C0.98990.81980.07140.129*
C151.1343 (4)0.6397 (3)0.0703 (4)0.0775 (13)
H15A1.12490.58090.02150.116*
H15B1.12910.61200.14060.116*
H15C1.20620.67270.06020.116*
C160.9286 (4)0.6723 (3)0.0698 (4)0.0812 (13)
H16A0.92030.61120.02340.122*
H16B0.87100.72470.05570.122*
H16C0.92270.64790.14110.122*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Rh10.03689 (12)0.04215 (11)0.04748 (13)0.00288 (10)0.00297 (13)0.00589 (12)
P10.0390 (4)0.0429 (4)0.0436 (5)0.0036 (3)0.0003 (4)0.0010 (4)
O10.0482 (14)0.0538 (13)0.0693 (17)0.0027 (11)0.0147 (13)0.0123 (12)
O20.0435 (12)0.0475 (11)0.0701 (16)0.0065 (9)0.0002 (14)0.0074 (12)
O30.070 (2)0.107 (2)0.114 (3)0.0069 (17)0.0280 (19)0.060 (2)
C10.046 (2)0.0538 (18)0.058 (2)0.0078 (16)0.0092 (17)0.0044 (16)
C20.0366 (18)0.067 (2)0.069 (2)0.0003 (16)0.0099 (18)0.009 (2)
C30.0394 (19)0.0510 (19)0.064 (2)0.0011 (14)0.0060 (17)0.0088 (15)
C40.053 (2)0.080 (2)0.122 (4)0.023 (2)0.006 (3)0.008 (3)
C50.079 (3)0.076 (2)0.087 (4)0.004 (2)0.027 (3)0.012 (2)
C60.048 (2)0.058 (2)0.072 (2)0.0092 (19)0.0060 (19)0.021 (2)
C70.0419 (18)0.0599 (18)0.070 (2)0.0023 (14)0.001 (2)0.004 (2)
C80.058 (3)0.074 (2)0.084 (3)0.017 (2)0.000 (2)0.000 (2)
C90.103 (4)0.127 (4)0.109 (4)0.046 (3)0.021 (4)0.001 (3)
C100.071 (3)0.0524 (19)0.050 (2)0.0138 (17)0.0017 (19)0.0093 (16)
C110.077 (3)0.068 (2)0.047 (2)0.0158 (17)0.002 (2)0.0063 (19)
C120.104 (4)0.099 (3)0.054 (3)0.015 (3)0.009 (3)0.008 (2)
C130.059 (2)0.0484 (18)0.054 (2)0.0023 (15)0.0041 (17)0.0062 (16)
C140.135 (5)0.079 (3)0.045 (2)0.005 (3)0.002 (3)0.012 (2)
C150.082 (3)0.059 (2)0.092 (3)0.021 (2)0.004 (3)0.018 (2)
C160.068 (3)0.070 (2)0.106 (3)0.011 (2)0.017 (3)0.023 (2)
Geometric parameters (Å, º) top
Rh1—C61.797 (4)C8—C91.267 (7)
Rh1—O12.036 (2)C8—H8A0.930
Rh1—O22.082 (2)C9—H9A0.930
Rh1—P12.2387 (8)C9—H9B0.930
P1—C101.826 (3)C10—C111.487 (5)
P1—C71.834 (3)C10—H10A0.970
P1—C131.869 (3)C10—H10B0.970
O1—C11.272 (4)C11—C121.270 (6)
O2—C31.264 (4)C11—H11A0.930
O3—C61.141 (4)C12—H12A0.930
C1—C21.377 (5)C12—H12B0.930
C1—C51.490 (5)C13—C161.528 (5)
C2—C31.395 (5)C13—C151.529 (5)
C2—H2A0.930C13—C141.536 (5)
C3—C41.500 (5)C14—H14A0.960
C4—H4A0.960C14—H14B0.960
C4—H4B0.960C14—H14C0.960
C4—H4C0.960C15—H15A0.960
C5—H5A0.960C15—H15B0.960
C5—H5B0.960C15—H15C0.960
C5—H5C0.960C16—H16A0.960
C7—C81.493 (5)C16—H16B0.960
C7—H7A0.970C16—H16C0.960
C7—H7B0.970
C6—Rh1—O1177.45 (14)C9—C8—C7125.3 (5)
C6—Rh1—O294.38 (13)C9—C8—H8A117.3
O1—Rh1—O288.03 (10)C7—C8—H8A117.3
C6—Rh1—P189.44 (12)C8—C9—H9A120.0
O1—Rh1—P188.15 (7)C8—C9—H9B120.0
O2—Rh1—P1176.15 (7)H9A—C9—H9B120.0
C10—P1—C7104.8 (2)C11—C10—P1115.2 (2)
C10—P1—C13104.03 (16)C11—C10—H10A108.5
C7—P1—C13103.08 (17)P1—C10—H10A108.5
C10—P1—Rh1111.84 (13)C11—C10—H10B108.5
C7—P1—Rh1117.82 (11)P1—C10—H10B108.5
C13—P1—Rh1113.89 (12)H10A—C10—H10B107.5
C1—O1—Rh1128.1 (2)C12—C11—C10126.0 (4)
C3—O2—Rh1126.5 (2)C12—C11—H11A117.0
O1—C1—C2125.0 (3)C10—C11—H11A117.0
O1—C1—C5114.9 (3)C11—C12—H12A120.0
C2—C1—C5120.1 (3)C11—C12—H12B120.0
C1—C2—C3126.9 (3)H12A—C12—H12B120.0
C1—C2—H2A116.5C16—C13—C15109.3 (3)
C3—C2—H2A116.5C16—C13—C14109.4 (4)
O2—C3—C2125.4 (3)C15—C13—C14110.0 (4)
O2—C3—C4115.6 (3)C16—C13—P1107.4 (3)
C2—C3—C4119.0 (3)C15—C13—P1112.6 (3)
C3—C4—H4A109.5C14—C13—P1107.9 (2)
C3—C4—H4B109.5C13—C14—H14A109.5
H4A—C4—H4B109.5C13—C14—H14B109.5
C3—C4—H4C109.5H14A—C14—H14B109.5
H4A—C4—H4C109.5C13—C14—H14C109.5
H4B—C4—H4C109.5H14A—C14—H14C109.5
C1—C5—H5A109.5H14B—C14—H14C109.5
C1—C5—H5B109.5C13—C15—H15A109.5
H5A—C5—H5B109.5C13—C15—H15B109.5
C1—C5—H5C109.5H15A—C15—H15B109.5
H5A—C5—H5C109.5C13—C15—H15C109.5
H5B—C5—H5C109.5H15A—C15—H15C109.5
O3—C6—Rh1178.8 (3)H15B—C15—H15C109.5
C8—C7—P1115.5 (3)C13—C16—H16A109.5
C8—C7—H7A108.4C13—C16—H16B109.5
P1—C7—H7A108.4H16A—C16—H16B109.5
C8—C7—H7B108.4C13—C16—H16C109.5
P1—C7—H7B108.4H16A—C16—H16C109.5
H7A—C7—H7B107.5H16B—C16—H16C109.5
 

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