Download citation
Download citation
link to html
In the title structure, [Fe(η-C5H4)2P{p-C6H5-C(CH3)3}] or [Fe(C20H21P)], 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

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536805003089/hb6147sup1.cif
Contains datablocks global, I

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536805003089/hb6147Isup2.hkl
Contains datablock I

CCDC reference: 269564

Key indicators

  • Single-crystal X-ray study
  • T = 150 K
  • Mean [sigma](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

Computing details top

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 = 348.19F(000) = 364
Triclinic, P1Dx = 1.406 Mg m3
Hall symbol: -P 1Mo Kα radiation, λ = 0.71073 Å
a = 8.0529 (3) ÅCell parameters from 15007 reflections
b = 10.1125 (4) Åθ = 2.6–27.5°
c = 10.3508 (4) ŵ = 1.01 mm1
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 tube2445 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.061
Detector resolution: 9 pixels mm-1θmax = 25.0°, θmin = 2.8°
φ scans and ω scans with κ offsetsh = 99
Absorption correction: multi-scan
(SORTAV; Blessing 1995)
k = 1211
Tmin = 0.755, Tmax = 0.789l = 1212
7882 measured reflections
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)] = 0.063H-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 reflectionsΔρmax = 0.84 e Å3
200 parametersΔρmin = 0.47 e Å3
0 restraintsExtinction correction: SHELXL97, Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
Primary atom site location: structure-invariant direct methodsExtinction 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
xyzUiso*/Ueq
Fe10.38837 (9)0.70205 (7)0.83296 (7)0.0270 (3)
P10.57578 (17)0.58157 (13)0.60780 (12)0.0263 (4)
C10.6199 (6)0.7152 (5)0.7161 (5)0.0266 (11)
C20.5277 (7)0.8399 (5)0.7114 (6)0.0329 (12)
H2A0.49740.88070.63060.039*
C30.4842 (7)0.8919 (6)0.8412 (6)0.0368 (13)
H3A0.41540.97340.86770.044*
C40.5498 (7)0.8039 (6)0.9281 (6)0.0371 (13)
H4A0.53470.81321.02590.045*
C50.6332 (7)0.6961 (5)0.8518 (5)0.0310 (12)
H5A0.68950.61930.88750.037*
C60.3679 (7)0.5499 (5)0.7198 (5)0.0291 (11)
C70.2311 (6)0.6428 (5)0.7160 (5)0.0300 (11)
H7A0.21160.69120.63520.036*
C80.1325 (7)0.6568 (6)0.8459 (6)0.0359 (13)
H8A0.03460.71900.87270.043*
C90.2025 (7)0.5737 (5)0.9326 (6)0.0357 (13)
H9A0.16120.56681.03090.043*
C100.3463 (7)0.5053 (5)0.8572 (5)0.0329 (12)
H10A0.41940.43960.89260.040*
C110.7062 (6)0.4467 (5)0.6505 (5)0.0265 (11)
C120.8735 (7)0.4687 (5)0.6566 (5)0.0311 (12)
H12A0.91740.55610.64400.037*
C130.9784 (7)0.3664 (5)0.6805 (5)0.0316 (12)
H13A1.09270.38540.68400.038*
C140.9204 (7)0.2348 (5)0.6999 (5)0.0270 (11)
C150.7518 (7)0.2135 (5)0.6918 (5)0.0313 (12)
H15A0.70810.12600.70260.038*
C160.6458 (7)0.3164 (5)0.6683 (5)0.0309 (12)
H16A0.53150.29830.66420.037*
C171.0374 (7)0.1254 (5)0.7320 (5)0.0305 (11)
C181.2017 (9)0.1237 (7)0.6262 (7)0.0538 (17)
H18A1.17580.10410.54040.081*
H18B1.27820.05560.64920.081*
H18C1.25680.21030.62090.081*
C191.0786 (10)0.1545 (8)0.8660 (7)0.0591 (19)
H19A0.97310.15560.93430.089*
H19B1.13430.24090.86130.089*
H19C1.15470.08580.88840.089*
C200.9554 (10)0.0107 (7)0.7423 (8)0.0599 (19)
H20A0.92760.03170.65750.090*
H20B0.85120.01090.81180.090*
H20C1.03470.07710.76430.090*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Fe10.0269 (4)0.0233 (4)0.0298 (5)0.0022 (3)0.0032 (3)0.0019 (3)
P10.0274 (7)0.0247 (7)0.0261 (7)0.0000 (5)0.0043 (5)0.0005 (5)
C10.021 (2)0.022 (2)0.036 (3)0.004 (2)0.004 (2)0.000 (2)
C20.033 (3)0.021 (3)0.045 (3)0.004 (2)0.008 (2)0.002 (2)
C30.034 (3)0.027 (3)0.048 (3)0.001 (2)0.005 (2)0.010 (2)
C40.037 (3)0.036 (3)0.039 (3)0.005 (2)0.010 (2)0.007 (2)
C50.028 (3)0.030 (3)0.035 (3)0.002 (2)0.008 (2)0.004 (2)
C60.026 (3)0.031 (3)0.031 (3)0.004 (2)0.008 (2)0.003 (2)
C70.024 (3)0.027 (3)0.040 (3)0.003 (2)0.008 (2)0.003 (2)
C80.030 (3)0.032 (3)0.043 (3)0.005 (2)0.002 (2)0.002 (2)
C90.033 (3)0.032 (3)0.036 (3)0.001 (2)0.003 (2)0.003 (2)
C100.034 (3)0.031 (3)0.033 (3)0.003 (2)0.005 (2)0.003 (2)
C110.027 (3)0.029 (3)0.023 (2)0.001 (2)0.003 (2)0.001 (2)
C120.031 (3)0.025 (3)0.036 (3)0.003 (2)0.003 (2)0.001 (2)
C130.023 (3)0.028 (3)0.043 (3)0.002 (2)0.005 (2)0.000 (2)
C140.030 (3)0.023 (3)0.027 (3)0.003 (2)0.003 (2)0.0006 (19)
C150.028 (3)0.027 (3)0.039 (3)0.003 (2)0.006 (2)0.003 (2)
C160.023 (3)0.031 (3)0.039 (3)0.001 (2)0.008 (2)0.000 (2)
C170.027 (3)0.027 (3)0.036 (3)0.000 (2)0.004 (2)0.001 (2)
C180.040 (4)0.055 (4)0.061 (4)0.017 (3)0.001 (3)0.009 (3)
C190.066 (5)0.066 (5)0.051 (4)0.025 (4)0.025 (4)0.004 (3)
C200.051 (4)0.034 (3)0.098 (6)0.006 (3)0.024 (4)0.011 (4)
Geometric parameters (Å, º) top
Fe1—C61.984 (5)C8—H8A1.0000
Fe1—C11.994 (5)C9—C101.431 (8)
Fe1—C102.021 (5)C9—H9A1.0000
Fe1—C52.023 (5)C10—H10A1.0000
Fe1—C22.029 (5)C11—C121.382 (7)
Fe1—C72.034 (5)C11—C161.402 (7)
Fe1—C92.072 (5)C12—C131.382 (8)
Fe1—C42.083 (6)C12—H12A0.9500
Fe1—C32.085 (5)C13—C141.409 (7)
Fe1—C82.089 (6)C13—H13A0.9500
Fe1—P12.7876 (15)C14—C151.397 (7)
P1—C111.820 (5)C14—C171.525 (7)
P1—C61.844 (5)C15—C161.391 (8)
P1—C11.860 (5)C15—H15A0.9500
C1—C51.440 (7)C16—H16A0.9500
C1—C21.464 (7)C17—C201.522 (8)
C2—C31.425 (8)C17—C181.525 (8)
C2—H2A1.0000C17—C191.530 (8)
C3—C41.429 (9)C18—H18A0.9800
C3—H3A1.0000C18—H18B0.9800
C4—C51.435 (8)C18—H18C0.9800
C4—H4A1.0000C19—H19A0.9800
C5—H5A1.0000C19—H19B0.9800
C6—C71.449 (8)C19—H19C0.9800
C6—C101.456 (7)C20—H20A0.9800
C7—C81.415 (8)C20—H20B0.9800
C7—H7A1.0000C20—H20C0.9800
C8—C91.417 (8)
C6—Fe1—C182.9 (2)C3—C4—H4A125.9
C6—Fe1—C1042.6 (2)C5—C4—H4A125.9
C1—Fe1—C10104.1 (2)Fe1—C4—H4A125.9
C6—Fe1—C5104.4 (2)C4—C5—C1109.0 (5)
C1—Fe1—C542.0 (2)C4—C5—Fe171.8 (3)
C10—Fe1—C596.3 (2)C1—C5—Fe167.9 (3)
C6—Fe1—C2105.9 (2)C4—C5—H5A125.5
C1—Fe1—C242.7 (2)C1—C5—H5A125.5
C10—Fe1—C2142.9 (2)Fe1—C5—H5A125.5
C5—Fe1—C269.7 (2)C7—C6—C10106.3 (5)
C6—Fe1—C742.3 (2)C7—C6—P1117.9 (4)
C1—Fe1—C7106.2 (2)C10—C6—P1124.2 (4)
C10—Fe1—C770.0 (2)C7—C6—Fe170.7 (3)
C5—Fe1—C7142.8 (2)C10—C6—Fe170.1 (3)
C2—Fe1—C7100.0 (2)P1—C6—Fe193.4 (2)
C6—Fe1—C970.1 (2)C8—C7—C6108.8 (5)
C1—Fe1—C9145.0 (2)C8—C7—Fe172.0 (3)
C10—Fe1—C940.9 (2)C6—C7—Fe167.0 (3)
C5—Fe1—C9123.6 (2)C8—C7—H7A125.6
C2—Fe1—C9166.4 (2)C6—C7—H7A125.6
C7—Fe1—C968.1 (2)Fe1—C7—H7A125.6
C6—Fe1—C4145.2 (2)C7—C8—C9108.4 (5)
C1—Fe1—C470.0 (2)C7—C8—Fe167.8 (3)
C10—Fe1—C4123.2 (2)C9—C8—Fe169.4 (3)
C5—Fe1—C440.9 (2)C7—C8—H8A125.7
C2—Fe1—C468.3 (2)C9—C8—H8A125.7
C7—Fe1—C4166.7 (2)Fe1—C8—H8A125.7
C9—Fe1—C4122.6 (2)C8—C9—C10108.8 (5)
C6—Fe1—C3146.4 (2)C8—C9—Fe170.7 (3)
C1—Fe1—C370.3 (2)C10—C9—Fe167.7 (3)
C10—Fe1—C3163.1 (2)C8—C9—H9A125.6
C5—Fe1—C368.7 (2)C10—C9—H9A125.6
C2—Fe1—C340.5 (2)Fe1—C9—H9A125.6
C7—Fe1—C3126.7 (2)C9—C10—C6107.7 (5)
C9—Fe1—C3142.0 (2)C9—C10—Fe171.4 (3)
C4—Fe1—C340.1 (2)C6—C10—Fe167.3 (3)
C6—Fe1—C869.7 (2)C9—C10—H10A126.2
C1—Fe1—C8146.3 (2)C6—C10—H10A126.2
C10—Fe1—C868.6 (2)Fe1—C10—H10A126.2
C5—Fe1—C8163.2 (2)C12—C11—C16117.8 (5)
C2—Fe1—C8126.7 (2)C12—C11—P1120.4 (4)
C7—Fe1—C840.1 (2)C16—C11—P1121.7 (4)
C9—Fe1—C839.8 (2)C13—C12—C11121.5 (5)
C4—Fe1—C8142.4 (2)C13—C12—H12A119.2
C3—Fe1—C8125.0 (2)C11—C12—H12A119.2
C6—Fe1—P141.32 (15)C12—C13—C14121.8 (5)
C1—Fe1—P141.79 (14)C12—C13—H13A119.1
C10—Fe1—P172.87 (15)C14—C13—H13A119.1
C5—Fe1—P173.08 (15)C15—C14—C13116.2 (5)
C2—Fe1—P170.19 (16)C15—C14—C17123.4 (4)
C7—Fe1—P169.84 (15)C13—C14—C17120.3 (5)
C9—Fe1—P1109.73 (16)C16—C15—C14122.0 (5)
C4—Fe1—P1110.17 (17)C16—C15—H15A119.0
C3—Fe1—P1108.29 (16)C14—C15—H15A119.0
C8—Fe1—P1107.45 (16)C15—C16—C11120.6 (5)
C11—P1—C6102.5 (2)C15—C16—H16A119.7
C11—P1—C1101.9 (2)C11—C16—H16A119.7
C6—P1—C190.6 (2)C20—C17—C18109.1 (5)
C11—P1—Fe1111.57 (16)C20—C17—C14112.6 (5)
C6—P1—Fe145.26 (16)C18—C17—C14109.8 (5)
C1—P1—Fe145.62 (15)C20—C17—C19107.9 (6)
C5—C1—C2105.9 (4)C18—C17—C19109.3 (6)
C5—C1—P1124.7 (4)C14—C17—C19108.0 (5)
C2—C1—P1116.8 (4)C17—C18—H18A109.5
C5—C1—Fe170.1 (3)C17—C18—H18B109.5
C2—C1—Fe170.0 (3)H18A—C18—H18B109.5
P1—C1—Fe192.6 (2)C17—C18—H18C109.5
C3—C2—C1108.9 (5)H18A—C18—H18C109.5
C3—C2—Fe171.8 (3)H18B—C18—H18C109.5
C1—C2—Fe167.4 (3)C17—C19—H19A109.5
C3—C2—H2A125.5C17—C19—H19B109.5
C1—C2—H2A125.5H19A—C19—H19B109.5
Fe1—C2—H2A125.5C17—C19—H19C109.5
C2—C3—C4108.0 (5)H19A—C19—H19C109.5
C2—C3—Fe167.7 (3)H19B—C19—H19C109.5
C4—C3—Fe169.9 (3)C17—C20—H20A109.5
C2—C3—H3A126.0C17—C20—H20B109.5
C4—C3—H3A126.0H20A—C20—H20B109.5
Fe1—C3—H3A126.0C17—C20—H20C109.5
C3—C4—C5108.2 (5)H20A—C20—H20C109.5
C3—C4—Fe170.0 (3)H20B—C20—H20C109.5
C5—C4—Fe167.3 (3)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
C13—H13A···Cg2i0.952.933.659 (6)135
C20—H20B···Cg1ii0.983.093.693 (8)121
Symmetry codes: (i) x+1, y, z; (ii) x, y1, z.
 

Follow Acta Cryst. E
Sign up for e-alerts
Follow Acta Cryst. on Twitter
Follow us on facebook
Sign up for RSS feeds