In the title structure, [Fe(η-C
5H
4)
2P{
p-C
6H
5-C(CH
3)
3}] or [Fe(C
20H
21P)], the cyclopentadienyl (Cp) rings of the ferrocenophane are tilted towards the bridging P atom, with a tilt angle of 26.9 (3)°. Weak intermolecular C—H
π(Cp-ring) interactions link molecules into sheets parallel to the
bc plane.
Supporting information
CCDC reference: 269564
Key indicators
- Single-crystal X-ray study
- T = 150 K
- Mean (C-C) = 0.008 Å
- R factor = 0.063
- wR factor = 0.165
- Data-to-parameter ratio = 14.4
checkCIF/PLATON results
No syntax errors found
Alert level B
PLAT432_ALERT_2_B Short Inter X...Y Contact P1 .. P1 .. 3.25 Ang.
Alert level C
CRYSC01_ALERT_1_C The word below has not been recognised as a standard
identifier.
deep
PLAT242_ALERT_2_C Check Low Ueq as Compared to Neighbors for C17
PLAT341_ALERT_3_C Low Bond Precision on C-C bonds (x 1000) Ang ... 8
PLAT480_ALERT_4_C Long H...A H-Bond Reported H13A .. CG2 .. 2.93 Ang.
PLAT480_ALERT_4_C Long H...A H-Bond Reported H20B .. CG1 .. 3.09 Ang.
0 ALERT level A = In general: serious problem
1 ALERT level B = Potentially serious problem
5 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
2 ALERT type 2 Indicator that the structure model may be wrong or deficient
1 ALERT type 3 Indicator that the structure quality may be low
2 ALERT type 4 Improvement, methodology, query or suggestion
Data collection: COLLECT (Nonius, 2003); cell refinement: DENZO-SMN (Otwinowski & Minor, 1997); data reduction: DENZO-SMN; program(s) used to solve structure: SHELXTL (Sheldrick, 2001); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL and PLATON (Spek, 2004); software used to prepare material for publication: SHELXTL.
(4-
tert-butylphenyl)phospha[1]ferrocenophane
top
Crystal data top
[Fe(C20H21P)] | Z = 2 |
Mr = 348.19 | F(000) = 364 |
Triclinic, P1 | Dx = 1.406 Mg m−3 |
Hall symbol: -P 1 | Mo Kα radiation, λ = 0.71073 Å |
a = 8.0529 (3) Å | Cell parameters from 15007 reflections |
b = 10.1125 (4) Å | θ = 2.6–27.5° |
c = 10.3508 (4) Å | µ = 1.01 mm−1 |
α = 88.706 (2)° | T = 150 K |
β = 77.492 (2)° | Block, deep red |
γ = 89.568 (2)° | 0.30 × 0.24 × 0.23 mm |
V = 822.70 (6) Å3 | |
Data collection top
Nonius KappaCCD diffractometer | 2877 independent reflections |
Radiation source: fine-focus sealed tube | 2445 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.061 |
Detector resolution: 9 pixels mm-1 | θmax = 25.0°, θmin = 2.8° |
φ scans and ω scans with κ offsets | h = −9→9 |
Absorption correction: multi-scan (SORTAV; Blessing 1995) | k = −12→11 |
Tmin = 0.755, Tmax = 0.789 | l = −12→12 |
7882 measured reflections | |
Refinement top
Refinement on F2 | Secondary atom site location: difference Fourier map |
Least-squares matrix: full | Hydrogen site location: inferred from neighbouring sites |
R[F2 > 2σ(F2)] = 0.063 | H-atom parameters constrained |
wR(F2) = 0.165 | w = 1/[σ2(Fo2) + 3.5656P] where P = (Fo2 + 2Fc2)/3 |
S = 1.12 | (Δ/σ)max < 0.001 |
2877 reflections | Δρmax = 0.84 e Å−3 |
200 parameters | Δρmin = −0.47 e Å−3 |
0 restraints | Extinction correction: SHELXL97, Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4 |
Primary atom site location: structure-invariant direct methods | Extinction coefficient: 0.022 (5) |
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 | x | y | z | Uiso*/Ueq | |
Fe1 | 0.38837 (9) | 0.70205 (7) | 0.83296 (7) | 0.0270 (3) | |
P1 | 0.57578 (17) | 0.58157 (13) | 0.60780 (12) | 0.0263 (4) | |
C1 | 0.6199 (6) | 0.7152 (5) | 0.7161 (5) | 0.0266 (11) | |
C2 | 0.5277 (7) | 0.8399 (5) | 0.7114 (6) | 0.0329 (12) | |
H2A | 0.4974 | 0.8807 | 0.6306 | 0.039* | |
C3 | 0.4842 (7) | 0.8919 (6) | 0.8412 (6) | 0.0368 (13) | |
H3A | 0.4154 | 0.9734 | 0.8677 | 0.044* | |
C4 | 0.5498 (7) | 0.8039 (6) | 0.9281 (6) | 0.0371 (13) | |
H4A | 0.5347 | 0.8132 | 1.0259 | 0.045* | |
C5 | 0.6332 (7) | 0.6961 (5) | 0.8518 (5) | 0.0310 (12) | |
H5A | 0.6895 | 0.6193 | 0.8875 | 0.037* | |
C6 | 0.3679 (7) | 0.5499 (5) | 0.7198 (5) | 0.0291 (11) | |
C7 | 0.2311 (6) | 0.6428 (5) | 0.7160 (5) | 0.0300 (11) | |
H7A | 0.2116 | 0.6912 | 0.6352 | 0.036* | |
C8 | 0.1325 (7) | 0.6568 (6) | 0.8459 (6) | 0.0359 (13) | |
H8A | 0.0346 | 0.7190 | 0.8727 | 0.043* | |
C9 | 0.2025 (7) | 0.5737 (5) | 0.9326 (6) | 0.0357 (13) | |
H9A | 0.1612 | 0.5668 | 1.0309 | 0.043* | |
C10 | 0.3463 (7) | 0.5053 (5) | 0.8572 (5) | 0.0329 (12) | |
H10A | 0.4194 | 0.4396 | 0.8926 | 0.040* | |
C11 | 0.7062 (6) | 0.4467 (5) | 0.6505 (5) | 0.0265 (11) | |
C12 | 0.8735 (7) | 0.4687 (5) | 0.6566 (5) | 0.0311 (12) | |
H12A | 0.9174 | 0.5561 | 0.6440 | 0.037* | |
C13 | 0.9784 (7) | 0.3664 (5) | 0.6805 (5) | 0.0316 (12) | |
H13A | 1.0927 | 0.3854 | 0.6840 | 0.038* | |
C14 | 0.9204 (7) | 0.2348 (5) | 0.6999 (5) | 0.0270 (11) | |
C15 | 0.7518 (7) | 0.2135 (5) | 0.6918 (5) | 0.0313 (12) | |
H15A | 0.7081 | 0.1260 | 0.7026 | 0.038* | |
C16 | 0.6458 (7) | 0.3164 (5) | 0.6683 (5) | 0.0309 (12) | |
H16A | 0.5315 | 0.2983 | 0.6642 | 0.037* | |
C17 | 1.0374 (7) | 0.1254 (5) | 0.7320 (5) | 0.0305 (11) | |
C18 | 1.2017 (9) | 0.1237 (7) | 0.6262 (7) | 0.0538 (17) | |
H18A | 1.1758 | 0.1041 | 0.5404 | 0.081* | |
H18B | 1.2782 | 0.0556 | 0.6492 | 0.081* | |
H18C | 1.2568 | 0.2103 | 0.6209 | 0.081* | |
C19 | 1.0786 (10) | 0.1545 (8) | 0.8660 (7) | 0.0591 (19) | |
H19A | 0.9731 | 0.1556 | 0.9343 | 0.089* | |
H19B | 1.1343 | 0.2409 | 0.8613 | 0.089* | |
H19C | 1.1547 | 0.0858 | 0.8884 | 0.089* | |
C20 | 0.9554 (10) | −0.0107 (7) | 0.7423 (8) | 0.0599 (19) | |
H20A | 0.9276 | −0.0317 | 0.6575 | 0.090* | |
H20B | 0.8512 | −0.0109 | 0.8118 | 0.090* | |
H20C | 1.0347 | −0.0771 | 0.7643 | 0.090* | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
Fe1 | 0.0269 (4) | 0.0233 (4) | 0.0298 (5) | −0.0022 (3) | −0.0032 (3) | −0.0019 (3) |
P1 | 0.0274 (7) | 0.0247 (7) | 0.0261 (7) | 0.0000 (5) | −0.0043 (5) | 0.0005 (5) |
C1 | 0.021 (2) | 0.022 (2) | 0.036 (3) | −0.004 (2) | −0.004 (2) | 0.000 (2) |
C2 | 0.033 (3) | 0.021 (3) | 0.045 (3) | −0.004 (2) | −0.008 (2) | 0.002 (2) |
C3 | 0.034 (3) | 0.027 (3) | 0.048 (3) | −0.001 (2) | −0.005 (2) | −0.010 (2) |
C4 | 0.037 (3) | 0.036 (3) | 0.039 (3) | −0.005 (2) | −0.010 (2) | −0.007 (2) |
C5 | 0.028 (3) | 0.030 (3) | 0.035 (3) | −0.002 (2) | −0.008 (2) | −0.004 (2) |
C6 | 0.026 (3) | 0.031 (3) | 0.031 (3) | −0.004 (2) | −0.008 (2) | −0.003 (2) |
C7 | 0.024 (3) | 0.027 (3) | 0.040 (3) | −0.003 (2) | −0.008 (2) | −0.003 (2) |
C8 | 0.030 (3) | 0.032 (3) | 0.043 (3) | −0.005 (2) | −0.002 (2) | −0.002 (2) |
C9 | 0.033 (3) | 0.032 (3) | 0.036 (3) | −0.001 (2) | 0.003 (2) | 0.003 (2) |
C10 | 0.034 (3) | 0.031 (3) | 0.033 (3) | −0.003 (2) | −0.005 (2) | 0.003 (2) |
C11 | 0.027 (3) | 0.029 (3) | 0.023 (2) | 0.001 (2) | −0.003 (2) | −0.001 (2) |
C12 | 0.031 (3) | 0.025 (3) | 0.036 (3) | −0.003 (2) | −0.003 (2) | 0.001 (2) |
C13 | 0.023 (3) | 0.028 (3) | 0.043 (3) | −0.002 (2) | −0.005 (2) | 0.000 (2) |
C14 | 0.030 (3) | 0.023 (3) | 0.027 (3) | −0.003 (2) | −0.003 (2) | 0.0006 (19) |
C15 | 0.028 (3) | 0.027 (3) | 0.039 (3) | −0.003 (2) | −0.006 (2) | 0.003 (2) |
C16 | 0.023 (3) | 0.031 (3) | 0.039 (3) | −0.001 (2) | −0.008 (2) | 0.000 (2) |
C17 | 0.027 (3) | 0.027 (3) | 0.036 (3) | 0.000 (2) | −0.004 (2) | 0.001 (2) |
C18 | 0.040 (4) | 0.055 (4) | 0.061 (4) | 0.017 (3) | 0.001 (3) | 0.009 (3) |
C19 | 0.066 (5) | 0.066 (5) | 0.051 (4) | 0.025 (4) | −0.025 (4) | −0.004 (3) |
C20 | 0.051 (4) | 0.034 (3) | 0.098 (6) | 0.006 (3) | −0.024 (4) | 0.011 (4) |
Geometric parameters (Å, º) top
Fe1—C6 | 1.984 (5) | C8—H8A | 1.0000 |
Fe1—C1 | 1.994 (5) | C9—C10 | 1.431 (8) |
Fe1—C10 | 2.021 (5) | C9—H9A | 1.0000 |
Fe1—C5 | 2.023 (5) | C10—H10A | 1.0000 |
Fe1—C2 | 2.029 (5) | C11—C12 | 1.382 (7) |
Fe1—C7 | 2.034 (5) | C11—C16 | 1.402 (7) |
Fe1—C9 | 2.072 (5) | C12—C13 | 1.382 (8) |
Fe1—C4 | 2.083 (6) | C12—H12A | 0.9500 |
Fe1—C3 | 2.085 (5) | C13—C14 | 1.409 (7) |
Fe1—C8 | 2.089 (6) | C13—H13A | 0.9500 |
Fe1—P1 | 2.7876 (15) | C14—C15 | 1.397 (7) |
P1—C11 | 1.820 (5) | C14—C17 | 1.525 (7) |
P1—C6 | 1.844 (5) | C15—C16 | 1.391 (8) |
P1—C1 | 1.860 (5) | C15—H15A | 0.9500 |
C1—C5 | 1.440 (7) | C16—H16A | 0.9500 |
C1—C2 | 1.464 (7) | C17—C20 | 1.522 (8) |
C2—C3 | 1.425 (8) | C17—C18 | 1.525 (8) |
C2—H2A | 1.0000 | C17—C19 | 1.530 (8) |
C3—C4 | 1.429 (9) | C18—H18A | 0.9800 |
C3—H3A | 1.0000 | C18—H18B | 0.9800 |
C4—C5 | 1.435 (8) | C18—H18C | 0.9800 |
C4—H4A | 1.0000 | C19—H19A | 0.9800 |
C5—H5A | 1.0000 | C19—H19B | 0.9800 |
C6—C7 | 1.449 (8) | C19—H19C | 0.9800 |
C6—C10 | 1.456 (7) | C20—H20A | 0.9800 |
C7—C8 | 1.415 (8) | C20—H20B | 0.9800 |
C7—H7A | 1.0000 | C20—H20C | 0.9800 |
C8—C9 | 1.417 (8) | | |
| | | |
C6—Fe1—C1 | 82.9 (2) | C3—C4—H4A | 125.9 |
C6—Fe1—C10 | 42.6 (2) | C5—C4—H4A | 125.9 |
C1—Fe1—C10 | 104.1 (2) | Fe1—C4—H4A | 125.9 |
C6—Fe1—C5 | 104.4 (2) | C4—C5—C1 | 109.0 (5) |
C1—Fe1—C5 | 42.0 (2) | C4—C5—Fe1 | 71.8 (3) |
C10—Fe1—C5 | 96.3 (2) | C1—C5—Fe1 | 67.9 (3) |
C6—Fe1—C2 | 105.9 (2) | C4—C5—H5A | 125.5 |
C1—Fe1—C2 | 42.7 (2) | C1—C5—H5A | 125.5 |
C10—Fe1—C2 | 142.9 (2) | Fe1—C5—H5A | 125.5 |
C5—Fe1—C2 | 69.7 (2) | C7—C6—C10 | 106.3 (5) |
C6—Fe1—C7 | 42.3 (2) | C7—C6—P1 | 117.9 (4) |
C1—Fe1—C7 | 106.2 (2) | C10—C6—P1 | 124.2 (4) |
C10—Fe1—C7 | 70.0 (2) | C7—C6—Fe1 | 70.7 (3) |
C5—Fe1—C7 | 142.8 (2) | C10—C6—Fe1 | 70.1 (3) |
C2—Fe1—C7 | 100.0 (2) | P1—C6—Fe1 | 93.4 (2) |
C6—Fe1—C9 | 70.1 (2) | C8—C7—C6 | 108.8 (5) |
C1—Fe1—C9 | 145.0 (2) | C8—C7—Fe1 | 72.0 (3) |
C10—Fe1—C9 | 40.9 (2) | C6—C7—Fe1 | 67.0 (3) |
C5—Fe1—C9 | 123.6 (2) | C8—C7—H7A | 125.6 |
C2—Fe1—C9 | 166.4 (2) | C6—C7—H7A | 125.6 |
C7—Fe1—C9 | 68.1 (2) | Fe1—C7—H7A | 125.6 |
C6—Fe1—C4 | 145.2 (2) | C7—C8—C9 | 108.4 (5) |
C1—Fe1—C4 | 70.0 (2) | C7—C8—Fe1 | 67.8 (3) |
C10—Fe1—C4 | 123.2 (2) | C9—C8—Fe1 | 69.4 (3) |
C5—Fe1—C4 | 40.9 (2) | C7—C8—H8A | 125.7 |
C2—Fe1—C4 | 68.3 (2) | C9—C8—H8A | 125.7 |
C7—Fe1—C4 | 166.7 (2) | Fe1—C8—H8A | 125.7 |
C9—Fe1—C4 | 122.6 (2) | C8—C9—C10 | 108.8 (5) |
C6—Fe1—C3 | 146.4 (2) | C8—C9—Fe1 | 70.7 (3) |
C1—Fe1—C3 | 70.3 (2) | C10—C9—Fe1 | 67.7 (3) |
C10—Fe1—C3 | 163.1 (2) | C8—C9—H9A | 125.6 |
C5—Fe1—C3 | 68.7 (2) | C10—C9—H9A | 125.6 |
C2—Fe1—C3 | 40.5 (2) | Fe1—C9—H9A | 125.6 |
C7—Fe1—C3 | 126.7 (2) | C9—C10—C6 | 107.7 (5) |
C9—Fe1—C3 | 142.0 (2) | C9—C10—Fe1 | 71.4 (3) |
C4—Fe1—C3 | 40.1 (2) | C6—C10—Fe1 | 67.3 (3) |
C6—Fe1—C8 | 69.7 (2) | C9—C10—H10A | 126.2 |
C1—Fe1—C8 | 146.3 (2) | C6—C10—H10A | 126.2 |
C10—Fe1—C8 | 68.6 (2) | Fe1—C10—H10A | 126.2 |
C5—Fe1—C8 | 163.2 (2) | C12—C11—C16 | 117.8 (5) |
C2—Fe1—C8 | 126.7 (2) | C12—C11—P1 | 120.4 (4) |
C7—Fe1—C8 | 40.1 (2) | C16—C11—P1 | 121.7 (4) |
C9—Fe1—C8 | 39.8 (2) | C13—C12—C11 | 121.5 (5) |
C4—Fe1—C8 | 142.4 (2) | C13—C12—H12A | 119.2 |
C3—Fe1—C8 | 125.0 (2) | C11—C12—H12A | 119.2 |
C6—Fe1—P1 | 41.32 (15) | C12—C13—C14 | 121.8 (5) |
C1—Fe1—P1 | 41.79 (14) | C12—C13—H13A | 119.1 |
C10—Fe1—P1 | 72.87 (15) | C14—C13—H13A | 119.1 |
C5—Fe1—P1 | 73.08 (15) | C15—C14—C13 | 116.2 (5) |
C2—Fe1—P1 | 70.19 (16) | C15—C14—C17 | 123.4 (4) |
C7—Fe1—P1 | 69.84 (15) | C13—C14—C17 | 120.3 (5) |
C9—Fe1—P1 | 109.73 (16) | C16—C15—C14 | 122.0 (5) |
C4—Fe1—P1 | 110.17 (17) | C16—C15—H15A | 119.0 |
C3—Fe1—P1 | 108.29 (16) | C14—C15—H15A | 119.0 |
C8—Fe1—P1 | 107.45 (16) | C15—C16—C11 | 120.6 (5) |
C11—P1—C6 | 102.5 (2) | C15—C16—H16A | 119.7 |
C11—P1—C1 | 101.9 (2) | C11—C16—H16A | 119.7 |
C6—P1—C1 | 90.6 (2) | C20—C17—C18 | 109.1 (5) |
C11—P1—Fe1 | 111.57 (16) | C20—C17—C14 | 112.6 (5) |
C6—P1—Fe1 | 45.26 (16) | C18—C17—C14 | 109.8 (5) |
C1—P1—Fe1 | 45.62 (15) | C20—C17—C19 | 107.9 (6) |
C5—C1—C2 | 105.9 (4) | C18—C17—C19 | 109.3 (6) |
C5—C1—P1 | 124.7 (4) | C14—C17—C19 | 108.0 (5) |
C2—C1—P1 | 116.8 (4) | C17—C18—H18A | 109.5 |
C5—C1—Fe1 | 70.1 (3) | C17—C18—H18B | 109.5 |
C2—C1—Fe1 | 70.0 (3) | H18A—C18—H18B | 109.5 |
P1—C1—Fe1 | 92.6 (2) | C17—C18—H18C | 109.5 |
C3—C2—C1 | 108.9 (5) | H18A—C18—H18C | 109.5 |
C3—C2—Fe1 | 71.8 (3) | H18B—C18—H18C | 109.5 |
C1—C2—Fe1 | 67.4 (3) | C17—C19—H19A | 109.5 |
C3—C2—H2A | 125.5 | C17—C19—H19B | 109.5 |
C1—C2—H2A | 125.5 | H19A—C19—H19B | 109.5 |
Fe1—C2—H2A | 125.5 | C17—C19—H19C | 109.5 |
C2—C3—C4 | 108.0 (5) | H19A—C19—H19C | 109.5 |
C2—C3—Fe1 | 67.7 (3) | H19B—C19—H19C | 109.5 |
C4—C3—Fe1 | 69.9 (3) | C17—C20—H20A | 109.5 |
C2—C3—H3A | 126.0 | C17—C20—H20B | 109.5 |
C4—C3—H3A | 126.0 | H20A—C20—H20B | 109.5 |
Fe1—C3—H3A | 126.0 | C17—C20—H20C | 109.5 |
C3—C4—C5 | 108.2 (5) | H20A—C20—H20C | 109.5 |
C3—C4—Fe1 | 70.0 (3) | H20B—C20—H20C | 109.5 |
C5—C4—Fe1 | 67.3 (3) | | |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
C13—H13A···Cg2i | 0.95 | 2.93 | 3.659 (6) | 135 |
C20—H20B···Cg1ii | 0.98 | 3.09 | 3.693 (8) | 121 |
Symmetry codes: (i) x+1, y, z; (ii) x, y−1, z. |