Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536803012091/ya6158sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S1600536803012091/ya6158Isup2.hkl |
CCDC reference: 217430
Key indicators
- Single-crystal X-ray study
- T = 298 K
- Mean (C-C) = 0.003 Å
- R factor = 0.029
- wR factor = 0.083
- Data-to-parameter ratio = 13.8
checkCIF results
No syntax errors found ADDSYM reports no extra symmetry
Alert Level C:
PLAT_710 Alert C Delete 1-2-3 or 2-3-4 (CIF) Linear Torsion Angle # 4 P1 -FE1 -P1 -C7 6.40 0.07 2.655 1.555 1.555 1.555 PLAT_710 Alert C Delete 1-2-3 or 2-3-4 (CIF) Linear Torsion Angle # 8 P1 -FE1 -P1 -C1 -116.51 0.07 2.655 1.555 1.555 1.555 PLAT_710 Alert C Delete 1-2-3 or 2-3-4 (CIF) Linear Torsion Angle # 12 P1 -FE1 -P1 -C20 130.16 0.08 2.655 1.555 1.555 1.555 PLAT_710 Alert C Delete 1-2-3 or 2-3-4 (CIF) Linear Torsion Angle # 58 C22 -FE1 -C21 -O1 -71.00 20.00 1.555 1.555 1.555 1.555 PLAT_710 Alert C Delete 1-2-3 or 2-3-4 (CIF) Linear Torsion Angle # 59 C21 -FE1 -C21 -O1 109.00 20.00 2.655 1.555 1.555 1.555 PLAT_710 Alert C Delete 1-2-3 or 2-3-4 (CIF) Linear Torsion Angle # 60 P1 -FE1 -C21 -O1 -161.00 20.00 1.555 1.555 1.555 1.555 PLAT_710 Alert C Delete 1-2-3 or 2-3-4 (CIF) Linear Torsion Angle # 61 P1 -FE1 -C21 -O1 20.00 20.00 2.655 1.555 1.555 1.555 PLAT_710 Alert C Delete 1-2-3 or 2-3-4 (CIF) Linear Torsion Angle # 62 C21 -FE1 -C22 -O3 -164.00100.00 2.655 1.555 1.555 1.555 PLAT_710 Alert C Delete 1-2-3 or 2-3-4 (CIF) Linear Torsion Angle # 63 C21 -FE1 -C22 -O3 16.00100.00 1.555 1.555 1.555 1.555 PLAT_710 Alert C Delete 1-2-3 or 2-3-4 (CIF) Linear Torsion Angle # 64 P1 -FE1 -C22 -O3 105.00100.00 1.555 1.555 1.555 1.555 PLAT_710 Alert C Delete 1-2-3 or 2-3-4 (CIF) Linear Torsion Angle # 65 P1 -FE1 -C22 -O3 -75.00100.00 2.655 1.555 1.555 1.555
0 Alert Level A = Potentially serious problem
0 Alert Level B = Potential problem
11 Alert Level C = Please check
Synthesis was carried out under Ar atmosphere. After the mixture of KOH(0.26 g, 4.6 mmol) and Fe(CO)5 (0.3 ml, 2.3 mmol) in CH3OH (20 ml) was stirred for 30 min, H2SO4 (0.46 g, 4.6 mmol) in 10 ml of CH3OH and Ph2PCH2COPh (1.39 g, 4.6 mmol) in 5 ml of CH2Cl2 were added. After stirring for 2 h, the resulting yellow solid was collected by filtration and dried in vacuo. Yield 1.43 g (83%).
All H atoms were placed in geometrically calculated positions and included in the refinement in the riding motion approximation, with Uiso(H)=1.2Ueq of the carrier carbon atom.
Data collection: Bruker SMART (Bruker, 1998); cell refinement: Bruker SMART; data reduction: Bruker SHELXTL (Bruker, 1997); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: Bruker SHELXTL; software used to prepare material for publication: Bruker SHELXTL.
Fig. 1. Molecular structure of the title compound. Displacement ellipsoids are drawn at the 30% probability level; the H atoms are omitted. |
[Fe(C20H17OP)(CO)3] | F(000) = 1552 |
Mr = 748.49 | Dx = 1.369 Mg m−3 |
Monoclinic, C2/c | Mo Kα radiation, λ = 0.71073 Å |
a = 20.4621 (14) Å | Cell parameters from 553 reflections |
b = 8.6575 (6) Å | θ = 2.6–22.3° |
c = 20.9787 (14) Å | µ = 0.55 mm−1 |
β = 102.342 (1)° | T = 298 K |
V = 3630.5 (4) Å3 | Plate, yellow |
Z = 4 | 0.40 × 0.35 × 0.20 mm |
CCD area detector diffractometer | 3203 independent reflections |
Radiation source: fine-focus sealed tube | 2656 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.010 |
ϕ and ω scans | θmax = 25.0°, θmin = 2.0° |
Absorption correction: multi-scan (SADABS; Sheldrick, 1996) | h = −20→24 |
Tmin = 0.874, Tmax = 0.936 | k = −10→10 |
7325 measured reflections | l = −23→24 |
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)] = 0.029 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.083 | H-atom parameters constrained |
S = 1.06 | w = 1/[σ2(Fo2) + (0.0453P)2 + 1.7565P] where P = (Fo2 + 2Fc2)/3 |
3203 reflections | (Δ/σ)max = 0.001 |
232 parameters | Δρmax = 0.24 e Å−3 |
0 restraints | Δρmin = −0.26 e Å−3 |
[Fe(C20H17OP)(CO)3] | V = 3630.5 (4) Å3 |
Mr = 748.49 | Z = 4 |
Monoclinic, C2/c | Mo Kα radiation |
a = 20.4621 (14) Å | µ = 0.55 mm−1 |
b = 8.6575 (6) Å | T = 298 K |
c = 20.9787 (14) Å | 0.40 × 0.35 × 0.20 mm |
β = 102.342 (1)° |
CCD area detector diffractometer | 3203 independent reflections |
Absorption correction: multi-scan (SADABS; Sheldrick, 1996) | 2656 reflections with I > 2σ(I) |
Tmin = 0.874, Tmax = 0.936 | Rint = 0.010 |
7325 measured reflections |
R[F2 > 2σ(F2)] = 0.029 | 0 restraints |
wR(F2) = 0.083 | H-atom parameters constrained |
S = 1.06 | Δρmax = 0.24 e Å−3 |
3203 reflections | Δρmin = −0.26 e Å−3 |
232 parameters |
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 | ||
Fe1 | 0.5000 | 0.60899 (4) | 0.2500 | 0.02855 (12) | |
P1 | 0.44951 (2) | 0.61152 (5) | 0.14569 (2) | 0.02946 (13) | |
O1 | 0.61366 (8) | 0.7711 (2) | 0.21637 (8) | 0.0637 (4) | |
O2 | 0.57564 (8) | 0.6373 (2) | 0.06666 (8) | 0.0638 (4) | |
O3 | 0.5000 | 0.2709 (2) | 0.2500 | 0.0522 (5) | |
C1 | 0.36502 (9) | 0.5285 (2) | 0.12348 (9) | 0.0366 (4) | |
C2 | 0.32580 (11) | 0.5476 (3) | 0.06132 (11) | 0.0640 (7) | |
H2A | 0.3410 | 0.6096 | 0.0313 | 0.077* | |
C3 | 0.26425 (13) | 0.4754 (4) | 0.04341 (13) | 0.0773 (8) | |
H3A | 0.2386 | 0.4891 | 0.0015 | 0.093* | |
C4 | 0.24084 (12) | 0.3840 (3) | 0.08691 (13) | 0.0653 (7) | |
H4A | 0.1995 | 0.3356 | 0.0747 | 0.078* | |
C5 | 0.27858 (11) | 0.3646 (3) | 0.14820 (12) | 0.0563 (6) | |
H5A | 0.2628 | 0.3024 | 0.1778 | 0.068* | |
C6 | 0.34052 (10) | 0.4368 (2) | 0.16706 (10) | 0.0430 (5) | |
H6A | 0.3656 | 0.4232 | 0.2092 | 0.052* | |
C7 | 0.43928 (9) | 0.8003 (2) | 0.10551 (8) | 0.0349 (4) | |
C8 | 0.43626 (11) | 0.8212 (3) | 0.03897 (10) | 0.0517 (5) | |
H8A | 0.4438 | 0.7378 | 0.0136 | 0.062* | |
C9 | 0.42209 (12) | 0.9647 (3) | 0.01048 (11) | 0.0591 (6) | |
H9A | 0.4202 | 0.9768 | −0.0339 | 0.071* | |
C10 | 0.41079 (11) | 1.0890 (2) | 0.04687 (11) | 0.0552 (6) | |
H10A | 0.4005 | 1.1848 | 0.0273 | 0.066* | |
C11 | 0.41469 (13) | 1.0710 (2) | 0.11232 (12) | 0.0592 (6) | |
H11A | 0.4073 | 1.1553 | 0.1374 | 0.071* | |
C12 | 0.42956 (11) | 0.9279 (2) | 0.14168 (10) | 0.0483 (5) | |
H12A | 0.4330 | 0.9179 | 0.1864 | 0.058* | |
C13 | 0.61637 (10) | 0.4173 (2) | 0.12767 (10) | 0.0434 (5) | |
C14 | 0.60503 (11) | 0.2708 (3) | 0.14895 (11) | 0.0534 (5) | |
H14A | 0.5615 | 0.2343 | 0.1438 | 0.064* | |
C15 | 0.65845 (14) | 0.1779 (3) | 0.17797 (14) | 0.0732 (7) | |
H15A | 0.6505 | 0.0789 | 0.1918 | 0.088* | |
C16 | 0.72235 (14) | 0.2309 (4) | 0.18627 (16) | 0.0846 (9) | |
H16A | 0.7578 | 0.1683 | 0.2060 | 0.102* | |
C17 | 0.73453 (13) | 0.3747 (4) | 0.16587 (18) | 0.0900 (10) | |
H17A | 0.7783 | 0.4106 | 0.1719 | 0.108* | |
C18 | 0.68197 (12) | 0.4680 (3) | 0.13608 (14) | 0.0693 (7) | |
H18A | 0.6907 | 0.5658 | 0.1215 | 0.083* | |
C19 | 0.56209 (10) | 0.5229 (2) | 0.09451 (9) | 0.0411 (4) | |
C20 | 0.48964 (9) | 0.4863 (2) | 0.09350 (9) | 0.0377 (4) | |
H20A | 0.4868 | 0.3800 | 0.1072 | 0.045* | |
H20B | 0.4644 | 0.4943 | 0.0489 | 0.045* | |
C21 | 0.56868 (10) | 0.7075 (2) | 0.22928 (8) | 0.0387 (4) | |
C22 | 0.5000 | 0.4047 (3) | 0.2500 | 0.0361 (6) |
U11 | U22 | U33 | U12 | U13 | U23 | |
Fe1 | 0.0289 (2) | 0.0323 (2) | 0.02270 (19) | 0.000 | 0.00155 (14) | 0.000 |
P1 | 0.0307 (3) | 0.0318 (3) | 0.0239 (2) | −0.00018 (18) | 0.00150 (18) | −0.00077 (17) |
O1 | 0.0551 (9) | 0.0793 (11) | 0.0606 (10) | −0.0266 (9) | 0.0212 (8) | −0.0055 (9) |
O2 | 0.0633 (10) | 0.0703 (11) | 0.0618 (10) | −0.0010 (8) | 0.0220 (8) | 0.0231 (9) |
O3 | 0.0655 (14) | 0.0347 (12) | 0.0545 (12) | 0.000 | 0.0089 (10) | 0.000 |
C1 | 0.0312 (9) | 0.0388 (10) | 0.0369 (10) | 0.0002 (8) | 0.0010 (8) | −0.0043 (8) |
C2 | 0.0478 (13) | 0.0931 (19) | 0.0438 (12) | −0.0196 (13) | −0.0069 (10) | 0.0100 (12) |
C3 | 0.0517 (14) | 0.110 (2) | 0.0566 (15) | −0.0225 (15) | −0.0189 (12) | 0.0044 (15) |
C4 | 0.0404 (12) | 0.0687 (16) | 0.0780 (17) | −0.0159 (11) | −0.0071 (12) | −0.0032 (13) |
C5 | 0.0435 (12) | 0.0519 (13) | 0.0711 (15) | −0.0111 (10) | 0.0065 (11) | 0.0056 (11) |
C6 | 0.0366 (10) | 0.0428 (11) | 0.0459 (11) | −0.0015 (8) | 0.0005 (9) | 0.0021 (9) |
C7 | 0.0343 (9) | 0.0364 (10) | 0.0310 (9) | −0.0016 (8) | 0.0002 (7) | 0.0037 (8) |
C8 | 0.0675 (14) | 0.0513 (12) | 0.0342 (10) | 0.0080 (11) | 0.0067 (10) | 0.0058 (9) |
C9 | 0.0708 (16) | 0.0621 (15) | 0.0403 (12) | 0.0017 (12) | 0.0028 (11) | 0.0177 (11) |
C10 | 0.0554 (13) | 0.0421 (12) | 0.0582 (14) | −0.0071 (10) | −0.0101 (11) | 0.0190 (10) |
C11 | 0.0776 (17) | 0.0352 (11) | 0.0618 (15) | 0.0015 (11) | 0.0081 (12) | 0.0021 (10) |
C12 | 0.0662 (14) | 0.0384 (11) | 0.0387 (11) | −0.0013 (10) | 0.0078 (10) | 0.0031 (9) |
C13 | 0.0418 (11) | 0.0482 (12) | 0.0419 (11) | 0.0041 (9) | 0.0123 (9) | −0.0091 (9) |
C14 | 0.0502 (12) | 0.0500 (13) | 0.0616 (14) | 0.0080 (10) | 0.0158 (10) | −0.0038 (11) |
C15 | 0.0723 (18) | 0.0548 (15) | 0.0921 (19) | 0.0221 (13) | 0.0167 (15) | −0.0001 (14) |
C16 | 0.0611 (18) | 0.080 (2) | 0.108 (2) | 0.0319 (15) | 0.0051 (16) | −0.0168 (18) |
C17 | 0.0383 (14) | 0.095 (2) | 0.132 (3) | 0.0076 (14) | 0.0080 (16) | −0.017 (2) |
C18 | 0.0473 (14) | 0.0673 (16) | 0.093 (2) | −0.0040 (12) | 0.0151 (13) | −0.0031 (14) |
C19 | 0.0469 (11) | 0.0473 (12) | 0.0304 (10) | 0.0004 (9) | 0.0115 (8) | −0.0054 (9) |
C20 | 0.0407 (10) | 0.0404 (10) | 0.0300 (9) | 0.0031 (8) | 0.0026 (8) | −0.0064 (8) |
C21 | 0.0409 (11) | 0.0470 (11) | 0.0262 (9) | −0.0046 (9) | 0.0025 (8) | −0.0028 (8) |
C22 | 0.0336 (14) | 0.0452 (17) | 0.0274 (13) | 0.000 | 0.0019 (10) | 0.000 |
Fe1—C22 | 1.769 (3) | C8—C9 | 1.382 (3) |
Fe1—C21i | 1.776 (2) | C8—H8A | 0.9300 |
Fe1—C21 | 1.776 (2) | C9—C10 | 1.367 (3) |
Fe1—P1 | 2.2113 (4) | C9—H9A | 0.9300 |
Fe1—P1i | 2.2113 (4) | C10—C11 | 1.367 (3) |
P1—C7 | 1.8302 (18) | C10—H10A | 0.9300 |
P1—C1 | 1.8382 (18) | C11—C12 | 1.388 (3) |
P1—C20 | 1.8527 (18) | C11—H11A | 0.9300 |
C1—C6 | 1.383 (3) | C12—H12A | 0.9300 |
C1—C2 | 1.387 (3) | C13—C14 | 1.380 (3) |
O1—C21 | 1.153 (2) | C13—C18 | 1.387 (3) |
O2—C19 | 1.212 (2) | C13—C19 | 1.491 (3) |
C2—C3 | 1.384 (3) | C14—C15 | 1.389 (3) |
C2—H2A | 0.9300 | C14—H14A | 0.9300 |
O3—C22 | 1.158 (3) | C15—C16 | 1.361 (4) |
C3—C4 | 1.369 (4) | C15—H15A | 0.9300 |
C3—H3A | 0.9300 | C16—C17 | 1.357 (4) |
C4—C5 | 1.361 (4) | C16—H16A | 0.9300 |
C4—H4A | 0.9300 | C17—C18 | 1.383 (4) |
C5—C6 | 1.393 (3) | C17—H17A | 0.9300 |
C5—H5A | 0.9300 | C18—H18A | 0.9300 |
C6—H6A | 0.9300 | C19—C20 | 1.512 (3) |
C7—C12 | 1.378 (3) | C20—H20A | 0.9700 |
C7—C8 | 1.396 (3) | C20—H20B | 0.9700 |
C22—Fe1—C21i | 118.71 (6) | C10—C9—H9A | 119.6 |
C22—Fe1—C21 | 118.71 (6) | C8—C9—H9A | 119.6 |
C21i—Fe1—C21 | 122.58 (13) | C11—C10—C9 | 119.4 (2) |
C22—Fe1—P1 | 90.568 (14) | C11—C10—H10A | 120.3 |
C21i—Fe1—P1 | 90.61 (6) | C9—C10—H10A | 120.3 |
C21—Fe1—P1 | 88.85 (6) | C10—C11—C12 | 120.5 (2) |
C22—Fe1—P1i | 90.568 (14) | C10—C11—H11A | 119.8 |
C21i—Fe1—P1i | 88.85 (6) | C12—C11—H11A | 119.8 |
C21—Fe1—P1i | 90.61 (6) | C7—C12—C11 | 120.99 (19) |
P1—Fe1—P1i | 178.86 (3) | C7—C12—H12A | 119.5 |
C7—P1—C1 | 102.94 (8) | C11—C12—H12A | 119.5 |
C7—P1—C20 | 105.77 (9) | C14—C13—C18 | 118.3 (2) |
C1—P1—C20 | 97.64 (8) | C14—C13—C19 | 123.7 (2) |
C7—P1—Fe1 | 116.61 (6) | C18—C13—C19 | 118.0 (2) |
C1—P1—Fe1 | 117.53 (6) | C13—C14—C15 | 120.2 (2) |
C20—P1—Fe1 | 113.99 (6) | C13—C14—H14A | 119.9 |
C6—C1—C2 | 118.12 (18) | C15—C14—H14A | 119.9 |
C6—C1—P1 | 120.74 (14) | C16—C15—C14 | 120.3 (3) |
C2—C1—P1 | 121.02 (16) | C16—C15—H15A | 119.8 |
C3—C2—C1 | 120.7 (2) | C14—C15—H15A | 119.8 |
C3—C2—H2A | 119.6 | C17—C16—C15 | 120.3 (3) |
C1—C2—H2A | 119.6 | C17—C16—H16A | 119.8 |
C4—C3—C2 | 120.5 (2) | C15—C16—H16A | 119.8 |
C4—C3—H3A | 119.7 | C16—C17—C18 | 120.1 (3) |
C2—C3—H3A | 119.7 | C16—C17—H17A | 120.0 |
C5—C4—C3 | 119.5 (2) | C18—C17—H17A | 120.0 |
C5—C4—H4A | 120.3 | C17—C18—C13 | 120.7 (3) |
C3—C4—H4A | 120.3 | C17—C18—H18A | 119.6 |
C4—C5—C6 | 120.7 (2) | C13—C18—H18A | 119.6 |
C4—C5—H5A | 119.6 | O2—C19—C13 | 120.12 (19) |
C6—C5—H5A | 119.6 | O2—C19—C20 | 119.32 (18) |
C1—C6—C5 | 120.4 (2) | C13—C19—C20 | 120.53 (18) |
C1—C6—H6A | 119.8 | C19—C20—P1 | 115.23 (13) |
C5—C6—H6A | 119.8 | C19—C20—H20A | 108.5 |
C12—C7—C8 | 117.75 (17) | P1—C20—H20A | 108.5 |
C12—C7—P1 | 118.54 (14) | C19—C20—H20B | 108.5 |
C8—C7—P1 | 123.56 (15) | P1—C20—H20B | 108.5 |
C9—C8—C7 | 120.6 (2) | H20A—C20—H20B | 107.5 |
C9—C8—H8A | 119.7 | O1—C21—Fe1 | 179.37 (18) |
C7—C8—H8A | 119.7 | O3—C22—Fe1 | 180.0 |
C10—C9—C8 | 120.7 (2) | ||
C22—Fe1—P1—C7 | −173.60 (7) | P1—C7—C8—C9 | 173.77 (17) |
C21i—Fe1—P1—C7 | 67.68 (9) | C7—C8—C9—C10 | 0.0 (4) |
C21—Fe1—P1—C7 | −54.89 (9) | C8—C9—C10—C11 | 1.1 (4) |
P1i—Fe1—P1—C7 | 6.40 (7) | C9—C10—C11—C12 | −0.4 (4) |
C22—Fe1—P1—C1 | 63.49 (7) | C8—C7—C12—C11 | 2.5 (3) |
C21i—Fe1—P1—C1 | −55.23 (9) | P1—C7—C12—C11 | −173.32 (18) |
C21—Fe1—P1—C1 | −177.81 (9) | C10—C11—C12—C7 | −1.4 (4) |
P1i—Fe1—P1—C1 | −116.51 (7) | C18—C13—C14—C15 | 0.0 (3) |
C22—Fe1—P1—C20 | −49.84 (7) | C19—C13—C14—C15 | 178.4 (2) |
C21i—Fe1—P1—C20 | −168.56 (9) | C13—C14—C15—C16 | 0.7 (4) |
C21—Fe1—P1—C20 | 68.86 (9) | C14—C15—C16—C17 | −0.5 (5) |
P1i—Fe1—P1—C20 | 130.16 (8) | C15—C16—C17—C18 | −0.4 (5) |
C7—P1—C1—C6 | −144.33 (16) | C16—C17—C18—C13 | 1.1 (5) |
C20—P1—C1—C6 | 107.48 (17) | C14—C13—C18—C17 | −0.9 (4) |
Fe1—P1—C1—C6 | −14.70 (18) | C19—C13—C18—C17 | −179.3 (3) |
C7—P1—C1—C2 | 39.9 (2) | C14—C13—C19—O2 | −166.6 (2) |
C20—P1—C1—C2 | −68.3 (2) | C18—C13—C19—O2 | 11.8 (3) |
Fe1—P1—C1—C2 | 169.50 (17) | C14—C13—C19—C20 | 11.6 (3) |
C6—C1—C2—C3 | −0.7 (4) | C18—C13—C19—C20 | −170.02 (19) |
P1—C1—C2—C3 | 175.2 (2) | O2—C19—C20—P1 | −73.4 (2) |
C1—C2—C3—C4 | 0.2 (5) | C13—C19—C20—P1 | 108.46 (18) |
C2—C3—C4—C5 | 0.1 (5) | C7—P1—C20—C19 | 71.13 (15) |
C3—C4—C5—C6 | 0.1 (4) | C1—P1—C20—C19 | 176.95 (14) |
C2—C1—C6—C5 | 0.9 (3) | Fe1—P1—C20—C19 | −58.29 (15) |
P1—C1—C6—C5 | −175.04 (17) | C22—Fe1—C21—O1 | −71 (20) |
C4—C5—C6—C1 | −0.6 (3) | C21i—Fe1—C21—O1 | 109 (20) |
C1—P1—C7—C12 | 97.22 (17) | P1—Fe1—C21—O1 | −161 (20) |
C20—P1—C7—C12 | −160.86 (16) | P1i—Fe1—C21—O1 | 20 (20) |
Fe1—P1—C7—C12 | −32.98 (18) | C21i—Fe1—C22—O3 | −164 (100) |
C1—P1—C7—C8 | −78.30 (18) | C21—Fe1—C22—O3 | 16 (100) |
C20—P1—C7—C8 | 23.62 (19) | P1—Fe1—C22—O3 | 105 (100) |
Fe1—P1—C7—C8 | 151.51 (15) | P1i—Fe1—C22—O3 | −75 (100) |
C12—C7—C8—C9 | −1.8 (3) |
Symmetry code: (i) −x+1, y, −z+1/2. |
Experimental details
Crystal data | |
Chemical formula | [Fe(C20H17OP)(CO)3] |
Mr | 748.49 |
Crystal system, space group | Monoclinic, C2/c |
Temperature (K) | 298 |
a, b, c (Å) | 20.4621 (14), 8.6575 (6), 20.9787 (14) |
β (°) | 102.342 (1) |
V (Å3) | 3630.5 (4) |
Z | 4 |
Radiation type | Mo Kα |
µ (mm−1) | 0.55 |
Crystal size (mm) | 0.40 × 0.35 × 0.20 |
Data collection | |
Diffractometer | CCD area detector diffractometer |
Absorption correction | Multi-scan (SADABS; Sheldrick, 1996) |
Tmin, Tmax | 0.874, 0.936 |
No. of measured, independent and observed [I > 2σ(I)] reflections | 7325, 3203, 2656 |
Rint | 0.010 |
(sin θ/λ)max (Å−1) | 0.595 |
Refinement | |
R[F2 > 2σ(F2)], wR(F2), S | 0.029, 0.083, 1.06 |
No. of reflections | 3203 |
No. of parameters | 232 |
H-atom treatment | H-atom parameters constrained |
Δρmax, Δρmin (e Å−3) | 0.24, −0.26 |
Computer programs: Bruker SMART (Bruker, 1998), Bruker SMART, Bruker SHELXTL (Bruker, 1997), SHELXS97 (Sheldrick, 1997), SHELXL97 (Sheldrick, 1997), Bruker SHELXTL.
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For many years we used trans-(Ph2Ppy)2Fe(CO)3 as neutral organometallic tridentate ligand and reacted it with various metal derivatives to yield a series of homo- and heterobinuclear complexes (Zhang & Cheng, 1996). Owing to the important role of hemilabile ligands containing a combination of soft and hard donor atoms (Jeffrey & Rauchfuss, 1979), we used Ph2PCH2COPh (Bouaoud et al., 1986) as a ligand to synthesize trans-(Ph2PCH2COPh)2Fe(CO)3. In the literature method, trans-(P)2Fe(CO)3 (P = phosphine ligand) is synthesized under basic conditions and some phosphine ligands containing functional groups such as COOH, etc. can therefore not be used.
Recently, we described a new synthetic route leading to trans-(Ph2PCH2COPh)2Fe(CO)3 (Cui et al., 2003), and now we report its crystal structure. According to the new synthesis, KOH is reacted with Fe(CO)5 to give KH(CO)4, and then H2SO4 and phosphine are added. The KH(CO)4 formed initially is then reacted with H2SO4 to give H2Fe(CO)4, which is activated by the excess of the acid and further reacted with the phosphine ligand, thus producing the target complex, trans-(Ph2PCH2COPh)2Fe(CO)3, (I), in high yield.
The structural study has shown that the molecule of the title compound (Fig. 1) occupies a special position: the Fe atom and one of the carbonyl groups lie on the twofold axis. The Fe atom has a trigonal-bipyramidal coordination environment, with two phosphine ligands in axial positions and three carbonyl groups lying on the equatorial plane. The PFeP unit has the expected parameters, with Fe—P distances of 2.2113 (4) Å and a P—Fe—P angle of 178.86 (3)°. Its geometry is comparable to those observed in trans-(Ph2Ppyrimidine)2Fe(CO)3 (Fe–P 2.202 Å, P—Fe—P 174.2°; Li et al., 1997) and trans-(Ph2Ppy)2Fe(CO)3 (2.206 Å, 177.1°; Zhang et al., 1996). The directions of the Fe—P bonds are almost exactly orthogonal to the equatorial FeC3 plane, all P—Fe—C angles being close to 90° [P1—Fe1—C21 88.85 (6), P1—Fe1—C22 90.568 (14), P1—Fe1—C21i 90.61 (6); symmetry code (i): 1 − x, y, 0.5 − z]. The C—Fe—C angles are not much different from the ideal value of 120° [C21—Fe1—C22 118.71 (6)°].