In the crystal structure of the title compound, [Fe2(C12H10P)2(CO)6]·CH2Cl2, the complex molecule lies across a mirror plane. Two diphosphide ligands bridge two (CO)3Fe fragments to form a dinuclear complex, in which the Fe—Fe distance is 2.6701 (6) Å. Two aromatic rings within the same molecule interact by face-to-face π–π stacking, with a centroid-to-centroid distance of 3.601 (2) Å.
Supporting information
CCDC reference: 282703
Key indicators
- Single-crystal X-ray study
- T = 293 K
- Mean (C-C) = 0.005 Å
- R factor = 0.044
- wR factor = 0.132
- Data-to-parameter ratio = 18.1
checkCIF/PLATON results
No syntax errors found
Alert level C
PLAT199_ALERT_1_C Check the Reported _cell_measurement_temperature 293 K
PLAT220_ALERT_2_C Large Non-Solvent C Ueq(max)/Ueq(min) ... 2.71 Ratio
PLAT232_ALERT_2_C Hirshfeld Test Diff (M-X) Fe - C10 .. 7.17 su
PLAT232_ALERT_2_C Hirshfeld Test Diff (M-X) Fe - C11 .. 6.10 su
PLAT232_ALERT_2_C Hirshfeld Test Diff (M-X) Fe - C12 .. 6.66 su
PLAT331_ALERT_2_C Small Average Phenyl C-C Dist. C21 -C22_b 1.37 Ang.
0 ALERT level A = In general: serious problem
0 ALERT level B = Potentially serious problem
6 ALERT level C = Check and explain
0 ALERT level G = General alerts; check
1 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
5 ALERT type 2 Indicator that the structure model may be wrong or deficient
0 ALERT type 3 Indicator that the structure quality may be low
0 ALERT type 4 Improvement, methodology, query or suggestion
Data collection: SMART (Bruker, 2000); cell refinement: SAINT (Bruker, 2000); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: SHELXTL (Bruker, 2000); software used to prepare material for publication: SHELXL97 and WinGX2003 (Farrugia, 1999).
Di-µ-diphenylphosphido-bis[tricarbonyliron(II)] dichloromethane solvate
top
Crystal data top
[Fe2(C12H10P)2(CO)6]·CH2Cl2 | F(000) = 744 |
Mr = 735.03 | Dx = 1.494 Mg m−3 |
Monoclinic, P21/m | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: -P 2yb | Cell parameters from 600 reflections |
a = 11.3218 (11) Å | θ = 20–25° |
b = 12.7214 (13) Å | µ = 1.19 mm−1 |
c = 11.8011 (12) Å | T = 293 K |
β = 105.976 (2)° | Rectangular, yellow |
V = 1634.1 (3) Å3 | 0.22 × 0.12 × 0.09 mm |
Z = 2 | |
Data collection top
Bruker SMART area-detector diffractometer | Rint = 0.022 |
Graphite monochromator | θmax = 27.5°, θmin = 1.8° |
φ and ω scans | h = −14→12 |
8071 measured reflections | k = −15→16 |
3826 independent reflections | l = −7→15 |
2896 reflections with I > 2σ(I) | |
Refinement top
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)] = 0.044 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.132 | H-atom parameters constrained |
S = 1.01 | w = 1/[σ2(Fo2) + (0.0878P)2] where P = (Fo2 + 2Fc2)/3 |
3826 reflections | (Δ/σ)max < 0.001 |
211 parameters | Δρmax = 1.17 e Å−3 |
0 restraints | Δρmin = −0.76 e Å−3 |
Special details top
Geometry. Bond distances, angles etc. have been calculated using the rounded
fractional coordinates. All e.s.d.'s are estimated from the variances of the
(full) variance-covariance matrix. The cell e.s.d.'s are taken into account in
the estimation of distances, angles and torsion angles |
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 | x | y | z | Uiso*/Ueq | |
Fe | 0.39139 (3) | 0.14753 (3) | 0.29892 (3) | 0.0335 (1) | |
P1 | 0.25204 (8) | 0.25000 | 0.34476 (8) | 0.0341 (3) | |
P2 | 0.34056 (8) | 0.25000 | 0.14062 (8) | 0.0323 (3) | |
O10 | 0.2581 (2) | −0.04789 (18) | 0.2297 (2) | 0.0665 (8) | |
O11 | 0.6258 (2) | 0.0945 (2) | 0.2550 (3) | 0.0899 (11) | |
O12 | 0.5111 (3) | 0.1175 (2) | 0.5507 (2) | 0.0752 (9) | |
C1 | 0.2380 (4) | 0.25000 | 0.4948 (3) | 0.0484 (14) | |
C2 | 0.2306 (4) | 0.1567 (3) | 0.5520 (3) | 0.0693 (14) | |
C3 | 0.2154 (5) | 0.1576 (4) | 0.6652 (4) | 0.099 (2) | |
C4 | 0.2076 (6) | 0.25000 | 0.7189 (5) | 0.102 (3) | |
C5 | 0.0890 (3) | 0.25000 | 0.2656 (3) | 0.0450 (14) | |
C6 | 0.0254 (3) | 0.1580 (3) | 0.2403 (4) | 0.0751 (13) | |
C7 | −0.1013 (3) | 0.1586 (4) | 0.1867 (4) | 0.098 (2) | |
C8 | −0.1627 (5) | 0.25000 | 0.1596 (5) | 0.090 (3) | |
C10 | 0.3093 (2) | 0.0285 (2) | 0.2564 (2) | 0.0427 (9) | |
C11 | 0.5349 (3) | 0.1158 (3) | 0.2707 (3) | 0.0518 (10) | |
C12 | 0.4628 (3) | 0.1281 (2) | 0.4536 (3) | 0.0489 (10) | |
C21 | 0.4315 (3) | 0.25000 | 0.0335 (3) | 0.0384 (11) | |
C22 | 0.4609 (3) | 0.1578 (2) | −0.0120 (3) | 0.0592 (11) | |
C23 | 0.5231 (4) | 0.1586 (3) | −0.0980 (3) | 0.0741 (16) | |
C24 | 0.5535 (5) | 0.25000 | −0.1395 (4) | 0.0722 (19) | |
C25 | 0.1870 (3) | 0.25000 | 0.0380 (3) | 0.0379 (11) | |
C26 | 0.1306 (3) | 0.1576 (3) | −0.0043 (3) | 0.0626 (12) | |
C27 | 0.0153 (4) | 0.1579 (3) | −0.0865 (3) | 0.0823 (16) | |
C28 | −0.0408 (5) | 0.25000 | −0.1272 (5) | 0.080 (2) | |
Cl1 | 0.8433 (4) | 0.1424 (3) | 0.5360 (3) | 0.379 (3) | |
C30 | 0.8992 (9) | 0.25000 | 0.4969 (9) | 0.131 (4) | |
H2 | 0.23570 | 0.09307 | 0.51491 | 0.0831* | |
H3 | 0.21060 | 0.09458 | 0.70369 | 0.1184* | |
H4 | 0.19662 | 0.25000 | 0.79414 | 0.1233* | |
H6 | 0.06660 | 0.09433 | 0.25883 | 0.0899* | |
H7 | −0.14349 | 0.09524 | 0.16963 | 0.1174* | |
H8 | −0.24655 | 0.25000 | 0.12248 | 0.1081* | |
H22 | 0.43902 | 0.09403 | 0.01503 | 0.0708* | |
H23 | 0.54389 | 0.09538 | −0.12716 | 0.0888* | |
H24 | 0.59558 | 0.25000 | −0.19698 | 0.0865* | |
H26 | 0.16921 | 0.09410 | 0.02180 | 0.0757* | |
H27 | −0.02326 | 0.09462 | −0.11359 | 0.0989* | |
H28 | −0.11719 | 0.25000 | −0.18260 | 0.0962* | |
H30A | 0.88361 | 0.25000 | 0.41182 | 0.1577* | |
H30B | 0.98758 | 0.25000 | 0.53092 | 0.1577* | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
Fe | 0.0317 (2) | 0.0326 (2) | 0.0339 (2) | 0.0018 (1) | 0.0050 (2) | 0.0019 (1) |
P1 | 0.0353 (5) | 0.0381 (5) | 0.0294 (5) | 0.0000 | 0.0095 (4) | 0.0000 |
P2 | 0.0316 (4) | 0.0346 (5) | 0.0307 (5) | 0.0000 | 0.0087 (4) | 0.0000 |
O10 | 0.0616 (13) | 0.0476 (13) | 0.0855 (17) | −0.0158 (11) | 0.0121 (12) | −0.0098 (12) |
O11 | 0.0485 (14) | 0.112 (2) | 0.115 (2) | 0.0262 (15) | 0.0321 (14) | 0.0180 (19) |
O12 | 0.0931 (18) | 0.0703 (15) | 0.0438 (13) | 0.0202 (13) | −0.0123 (12) | 0.0066 (11) |
C1 | 0.041 (2) | 0.071 (3) | 0.034 (2) | 0.0000 | 0.0115 (16) | 0.0000 |
C2 | 0.078 (2) | 0.080 (3) | 0.056 (2) | 0.0022 (18) | 0.0287 (19) | 0.0151 (17) |
C3 | 0.102 (3) | 0.143 (5) | 0.059 (3) | 0.011 (3) | 0.036 (2) | 0.039 (3) |
C4 | 0.087 (4) | 0.190 (8) | 0.037 (3) | 0.0000 | 0.028 (3) | 0.0000 |
C5 | 0.037 (2) | 0.067 (3) | 0.033 (2) | 0.0000 | 0.0131 (16) | 0.0000 |
C6 | 0.0424 (18) | 0.077 (2) | 0.105 (3) | −0.0072 (16) | 0.0188 (19) | −0.029 (2) |
C7 | 0.043 (2) | 0.139 (4) | 0.111 (4) | −0.023 (2) | 0.019 (2) | −0.053 (3) |
C8 | 0.038 (3) | 0.153 (7) | 0.079 (4) | 0.0000 | 0.015 (3) | 0.0000 |
C10 | 0.0404 (14) | 0.0436 (16) | 0.0431 (15) | 0.0025 (12) | 0.0097 (12) | −0.0001 (12) |
C11 | 0.0412 (16) | 0.0553 (17) | 0.0564 (19) | 0.0055 (14) | 0.0092 (14) | 0.0050 (15) |
C12 | 0.0536 (18) | 0.0389 (15) | 0.0474 (18) | 0.0071 (12) | 0.0027 (14) | 0.0022 (13) |
C21 | 0.0370 (19) | 0.042 (2) | 0.037 (2) | 0.0000 | 0.0115 (15) | 0.0000 |
C22 | 0.072 (2) | 0.0488 (18) | 0.067 (2) | −0.0043 (15) | 0.0362 (19) | −0.0068 (14) |
C23 | 0.098 (3) | 0.067 (2) | 0.077 (3) | 0.0095 (19) | 0.057 (2) | −0.0096 (18) |
C24 | 0.077 (3) | 0.094 (4) | 0.061 (3) | 0.0000 | 0.045 (3) | 0.0000 |
C25 | 0.0353 (18) | 0.055 (2) | 0.0242 (17) | 0.0000 | 0.0093 (14) | 0.0000 |
C26 | 0.057 (2) | 0.064 (2) | 0.054 (2) | −0.0153 (15) | −0.0064 (16) | 0.0037 (15) |
C27 | 0.059 (2) | 0.104 (3) | 0.068 (3) | −0.029 (2) | −0.0092 (19) | 0.000 (2) |
C28 | 0.045 (3) | 0.129 (5) | 0.055 (3) | 0.0000 | −0.006 (2) | 0.0000 |
Cl1 | 0.421 (5) | 0.487 (6) | 0.176 (2) | −0.355 (5) | −0.008 (3) | 0.052 (3) |
C30 | 0.133 (6) | 0.121 (6) | 0.170 (8) | 0.0000 | 0.093 (6) | 0.0000 |
Geometric parameters (Å, º) top
Fe—P1 | 2.2250 (9) | C21—C22 | 1.369 (3) |
Fe—P2 | 2.2200 (8) | C21—C22i | 1.369 (3) |
Fe—C10 | 1.775 (3) | C22—C23 | 1.385 (5) |
Fe—C11 | 1.792 (4) | C23—C24 | 1.343 (5) |
Fe—C12 | 1.798 (3) | C25—C26 | 1.365 (4) |
Fe—Fei | 2.6071 (6) | C25—C26i | 1.365 (4) |
Cl1—C30 | 1.627 (7) | C26—C27 | 1.396 (5) |
P1—C1 | 1.821 (4) | C27—C28 | 1.356 (5) |
P1—C5 | 1.825 (4) | C2—H2 | 0.9295 |
P2—C21 | 1.837 (4) | C3—H3 | 0.9304 |
P2—C25 | 1.825 (4) | C4—H4 | 0.9298 |
O10—C10 | 1.131 (3) | C6—H6 | 0.9302 |
O11—C11 | 1.128 (4) | C7—H7 | 0.9303 |
O12—C12 | 1.134 (4) | C8—H8 | 0.9296 |
C1—C2i | 1.379 (4) | C22—H22 | 0.9299 |
C1—C2 | 1.379 (4) | C23—H23 | 0.9302 |
C2—C3 | 1.393 (6) | C24—H24 | 0.9301 |
C3—C4 | 1.350 (6) | C26—H26 | 0.9297 |
C5—C6 | 1.363 (4) | C27—H27 | 0.9295 |
C5—C6i | 1.363 (4) | C28—H28 | 0.9296 |
C6—C7 | 1.399 (5) | C30—H30A | 0.9704 |
C7—C8 | 1.347 (6) | C30—H30B | 0.9702 |
| | | |
P1—Fe—P2 | 79.84 (3) | P2—C21—C22 | 120.86 (19) |
P1—Fe—C10 | 102.55 (8) | P2—C21—C22i | 120.86 (19) |
P1—Fe—C11 | 156.48 (12) | C22—C21—C22i | 118.0 (3) |
P1—Fe—C12 | 89.11 (11) | C21—C22—C23 | 120.6 (3) |
Fei—Fe—P1 | 54.14 (2) | C22—C23—C24 | 120.4 (4) |
P2—Fe—C10 | 105.59 (8) | C23—C24—C23i | 120.0 (5) |
P2—Fe—C11 | 90.81 (12) | P2—C25—C26 | 120.5 (2) |
P2—Fe—C12 | 151.02 (9) | P2—C25—C26i | 120.5 (2) |
Fei—Fe—P2 | 54.04 (2) | C26—C25—C26i | 118.9 (3) |
C10—Fe—C11 | 100.73 (14) | C25—C26—C27 | 120.4 (3) |
C10—Fe—C12 | 102.93 (12) | C26—C27—C28 | 120.4 (4) |
Fei—Fe—C10 | 148.53 (8) | C27—C28—C27i | 119.5 (5) |
C11—Fe—C12 | 88.87 (16) | C1—C2—H2 | 119.93 |
Fei—Fe—C11 | 103.02 (12) | C3—C2—H2 | 119.92 |
Fei—Fe—C12 | 97.90 (8) | C2—C3—H3 | 120.02 |
Fe—P1—C1 | 119.60 (11) | C4—C3—H3 | 120.07 |
Fe—P1—C5 | 124.09 (8) | C3—C4—H4 | 119.44 |
Fe—P1—Fei | 71.73 (3) | C3i—C4—H4 | 119.44 |
C1—P1—C5 | 98.69 (18) | C5—C6—H6 | 119.70 |
Fei—P1—C1 | 119.60 (11) | C7—C6—H6 | 119.76 |
Fei—P1—C5 | 124.09 (8) | C6—C7—H7 | 119.64 |
Fe—P2—C21 | 120.96 (9) | C8—C7—H7 | 119.72 |
Fe—P2—C25 | 122.51 (9) | C7—C8—H8 | 120.34 |
Fe—P2—Fei | 71.91 (3) | C7i—C8—H8 | 120.34 |
C21—P2—C25 | 98.94 (16) | C21—C22—H22 | 119.77 |
Fei—P2—C21 | 120.96 (9) | C23—C22—H22 | 119.66 |
Fei—P2—C25 | 122.51 (9) | C22—C23—H23 | 119.74 |
P1—C1—C2 | 120.6 (2) | C24—C23—H23 | 119.83 |
P1—C1—C2i | 120.6 (2) | C23—C24—H24 | 120.01 |
C2—C1—C2i | 118.7 (3) | C23i—C24—H24 | 120.01 |
C1—C2—C3 | 120.2 (4) | C25—C26—H26 | 119.81 |
C2—C3—C4 | 119.9 (5) | C27—C26—H26 | 119.81 |
C3—C4—C3i | 121.1 (5) | C26—C27—H27 | 119.84 |
P1—C5—C6 | 120.7 (2) | C28—C27—H27 | 119.77 |
P1—C5—C6i | 120.7 (2) | C27—C28—H28 | 120.23 |
C6—C5—C6i | 118.3 (3) | C27i—C28—H28 | 120.23 |
C5—C6—C7 | 120.5 (4) | Cl1—C30—Cl1i | 114.5 (7) |
C6—C7—C8 | 120.6 (4) | Cl1—C30—H30A | 108.62 |
C7—C8—C7i | 119.3 (5) | Cl1—C30—H30B | 108.66 |
Fe—C10—O10 | 179.3 (2) | H30A—C30—H30B | 107.54 |
Fe—C11—O11 | 178.5 (3) | Cl1i—C30—H30A | 108.62 |
Fe—C12—O12 | 177.8 (3) | Cl1i—C30—H30B | 108.66 |
| | | |
P1—Fe—Fei—P2 | −104.81 (4) | C12—Fe—P2—C25 | −133.9 (2) |
P2—Fe—Fei—P1 | 104.81 (4) | Fei—Fe—P2—C25 | −117.53 (10) |
C10—Fe—Fei—P1 | 48.13 (15) | P1—Fe—P2—Fei | 52.75 (3) |
C10—Fe—Fei—P2 | −56.68 (15) | C10—Fe—P2—Fei | 153.07 (8) |
C10—Fe—Fei—C10i | 0.0 (2) | C11—Fe—P2—Fei | −105.55 (12) |
C10—Fe—Fei—C11i | −138.07 (18) | C12—Fe—P2—Fei | −16.4 (2) |
C10—Fe—Fei—C12i | 131.26 (19) | P1—Fei—P2—Fe | −52.75 (3) |
C11—Fe—Fei—P1 | −173.80 (12) | Fe—Fei—P2—C21 | −115.80 (10) |
C11—Fe—Fei—P2 | 81.39 (12) | Fe—Fei—P2—C25 | 117.53 (10) |
C11—Fe—Fei—C10i | 138.07 (18) | Fe—P1—C1—C2 | −48.7 (4) |
C11—Fe—Fei—C11i | 0.00 (16) | C5—P1—C1—C2 | 89.0 (4) |
C11—Fe—Fei—C12i | −90.67 (16) | Fei—P1—C1—C2 | −133.4 (3) |
C12—Fe—Fei—P1 | −83.13 (12) | Fe—P1—C1—C2i | 133.4 (3) |
C12—Fe—Fei—P2 | 172.06 (12) | Fe—P1—C5—C6i | −138.2 (3) |
C12—Fe—Fei—C10i | −131.26 (19) | Fe—P1—C5—C6 | 48.1 (4) |
C12—Fe—Fei—C11i | 90.67 (16) | C1—P1—C5—C6 | −86.9 (3) |
C12—Fe—Fei—C12i | 0.00 (16) | Fei—P1—C5—C6 | 138.2 (3) |
P2—Fe—P1—C1 | −166.91 (12) | Fe—P2—C25—C26i | 136.6 (3) |
C10—Fe—P1—C1 | 89.22 (14) | Fei—P2—C25—C26 | −136.6 (3) |
C11—Fe—P1—C1 | −99.0 (3) | Fe—P2—C21—C22 | 50.2 (3) |
C12—Fe—P1—C1 | −13.83 (15) | Fe—P2—C21—C22i | −136.6 (3) |
Fei—Fe—P1—C1 | −114.25 (12) | Fei—P2—C21—C22 | 136.6 (3) |
P2—Fe—P1—C5 | 66.63 (10) | C21—P2—C25—C26 | 87.6 (3) |
C10—Fe—P1—C5 | −37.24 (13) | C25—P2—C21—C22 | −86.6 (3) |
C11—Fe—P1—C5 | 134.6 (3) | Fe—P2—C25—C26 | −48.3 (3) |
C12—Fe—P1—C5 | −140.29 (14) | C2i—C1—C2—C3 | 0.3 (7) |
Fei—Fe—P1—C5 | 119.29 (11) | P1—C1—C2—C3 | −177.7 (4) |
P2—Fe—P1—Fei | −52.66 (3) | C1—C2—C3—C4 | 0.2 (8) |
C10—Fe—P1—Fei | −156.53 (8) | C2—C3—C4—C3i | −0.6 (9) |
C11—Fe—P1—Fei | 15.3 (3) | P1—C5—C6—C7 | 175.7 (3) |
C12—Fe—P1—Fei | 100.42 (10) | C6i—C5—C6—C7 | 1.8 (6) |
P2—Fei—P1—Fe | 52.66 (3) | C5—C6—C7—C8 | −0.3 (7) |
Fe—Fei—P1—C1 | 114.25 (12) | C6—C7—C8—C7i | −1.3 (8) |
Fe—Fei—P1—C5 | −119.29 (11) | C22i—C21—C22—C23 | 2.6 (5) |
P1—Fe—P2—C21 | 168.55 (10) | P2—C21—C22—C23 | 176.1 (3) |
C10—Fe—P2—C21 | −91.13 (12) | C21—C22—C23—C24 | −1.2 (6) |
C11—Fe—P2—C21 | 10.26 (15) | C22—C23—C24—C23i | −0.3 (7) |
C12—Fe—P2—C21 | 99.4 (3) | P2—C25—C26—C27 | −177.3 (3) |
Fei—Fe—P2—C21 | 115.80 (10) | C26i—C25—C26—C27 | −2.1 (5) |
P1—Fe—P2—C25 | −64.78 (10) | C25—C26—C27—C28 | 1.4 (6) |
C10—Fe—P2—C25 | 35.54 (13) | C26—C27—C28—C27i | −0.7 (7) |
C11—Fe—P2—C25 | 136.92 (15) | | |
Symmetry code: (i) x, −y+1/2, z. |