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The mol­ecule of the title compound, [Fe(C10H15)(C11H11)], contains parallel and eclipsed five-membered rings coordinated to the central Fe atom at perpendicular distances of 1.642 (1) (cyclo­penta­dienyl ring) and 1.667 (1) Å (indenyl ring).

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536802003884/na6141sup1.cif
Contains datablocks I, global

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536802003884/na6141Isup2.hkl
Contains datablock I

CCDC reference: 183761

Key indicators

  • Single-crystal X-ray study
  • T = 178 K
  • Mean [sigma](C-C) = 0.004 Å
  • R factor = 0.036
  • wR factor = 0.089
  • Data-to-parameter ratio = 13.4

checkCIF results

No syntax errors found

ADDSYM reports no extra symmetry


Red Alert Alert Level A:
ABSTM_02 Alert A The ratio of Tmax/Tmin expected RT(exp) is > 1.30 An absorption correction should be applied. Tmin and Tmax expected: 0.661 0.876 RT(exp) = 1.325
Author response: This structure was measured many years ago when it was not usual to perform absorption corrections for mu values < 1. This is of course no longer the accepted procedure today but we cannot correct the old data.

Yellow Alert Alert Level C:
REFLT_03 From the CIF: _diffrn_reflns_theta_max 25.04 From the CIF: _reflns_number_total 2768 TEST2: Reflns within _diffrn_reflns_theta_max Count of symmetry unique reflns 2990 Completeness (_total/calc) 92.58% Alert C: < 95% complete
1 Alert Level A = Potentially serious problem
0 Alert Level B = Potential problem
1 Alert Level C = Please check

Computing details top

Data collection: P3 (Nicolet, 1987); cell refinement: P3; data reduction: XDISK (Nicolet, 1987); program(s) used to solve structure: SHELXS97 (Sheldrick, 1990); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: XP (Siemens, 1994); software used to prepare material for publication: SHELXL97.

(I) top
Crystal data top
[Fe(C10H15)(C11H11)]F(000) = 712
Mr = 334.27Dx = 1.311 Mg m3
Monoclinic, P21/nMo Kα radiation, λ = 0.71073 Å
a = 8.350 (2) ÅCell parameters from 48 reflections
b = 13.925 (3) Åθ = 10–12°
c = 14.645 (4) ŵ = 0.89 mm1
β = 95.88 (2)°T = 178 K
V = 1693.9 (7) Å3Tablet, red
Z = 40.6 × 0.4 × 0.15 mm
Data collection top
Nicolet R3
diffractometer
Rint = 0.020
Radiation source: fine-focus sealed tubeθmax = 25.0°, θmin = 3.1°
Graphite monochromatorh = 99
ω scansk = 160
2821 measured reflectionsl = 1717
2768 independent reflections3 standard reflections every 247 reflections
2191 reflections with I > 2σ(I) intensity decay: none
Refinement top
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.036Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.089H-atom parameters constrained
S = 1.04 w = 1/[σ2(Fo2) + (0.0459P)2 + 0.6303P]
where P = (Fo2 + 2Fc2)/3
2768 reflections(Δ/σ)max < 0.001
206 parametersΔρmax = 0.37 e Å3
0 restraintsΔρmin = 0.46 e Å3
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.

Least-squares planes (x,y,z in crystal coordinates) and deviations from them (* indicates atom used to define plane)

6.8902 (0.0063) x + 7.5580 (0.0146) y - 3.5185 (0.0181) z = 5.9829 (0.0059)

* -0.0095 (0.0015) C1 * 0.0117 (0.0016) C2 * -0.0093 (0.0015) C3 * 0.0034 (0.0015) C3A * 0.0037 (0.0015) C7A -1.6674 (0.0013) Fe

Rms deviation of fitted atoms = 0.0082

6.6563 (0.0066) x + 8.1033 (0.0141) y - 3.5402 (0.0175) z = 2.6580 (0.0055)

Angle to previous plane (with approximate e.s.d.) = 2.77 (0.17)

* 0.0029 (0.0015) C15 * -0.0009 (0.0015) C16 * -0.0016 (0.0015) C17 * 0.0034 (0.0015) C18 * -0.0039 (0.0015) C19 1.6420 (0.0012) Fe

Rms deviation of fitted atoms = 0.0028

6.8731 (0.0035) x + 7.5594 (0.0072) y - 3.6620 (0.0114) z = 5.9387 (0.0041)

Angle to previous plane (with approximate e.s.d.) = 2.71 (0.13)

* -0.0213 (0.0019) C1 * 0.0076 (0.0020) C2 * 0.0009 (0.0019) C3 * 0.0147 (0.0021) C3A * -0.0064 (0.0019) C4 * -0.0115 (0.0019) C5 * 0.0051 (0.0020) C6 * 0.0097 (0.0019) C7 * 0.0013 (0.0021) C7A -1.6668 (0.0012) Fe

Rms deviation of fitted atoms = 0.0107

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
Fe0.52436 (4)0.20614 (3)0.24314 (3)0.02232 (13)
C10.7191 (3)0.27768 (19)0.3070 (2)0.0310 (6)
H10.74670.28000.37150.040*
C20.7692 (3)0.2068 (2)0.2468 (2)0.0331 (6)
H20.83890.15450.26410.041*
C30.6982 (3)0.22666 (19)0.1563 (2)0.0320 (6)
H30.70940.18920.10320.041*
C3A0.6066 (3)0.31346 (18)0.15985 (19)0.0263 (6)
C40.5094 (3)0.36557 (19)0.09070 (19)0.0289 (6)
C50.4347 (3)0.4457 (2)0.1174 (2)0.0326 (6)
H50.36930.48150.07260.041*
C60.4506 (3)0.4784 (2)0.2102 (2)0.0334 (7)
H60.39670.53560.22480.041*
C70.5401 (3)0.4308 (2)0.2786 (2)0.0308 (6)
C7A0.6200 (3)0.34510 (19)0.25397 (18)0.0258 (6)
C80.5600 (4)0.4643 (2)0.3762 (2)0.0431 (8)
H8A0.49470.52200.38220.052*
H8B0.67350.47920.39420.052*
H8C0.52470.41360.41600.052*
C90.4931 (4)0.3302 (2)0.0062 (2)0.0393 (7)
H9A0.41010.36750.04270.047*
H9B0.46240.26220.00740.047*
H9C0.59610.33760.03200.047*
C100.4092 (3)0.0361 (2)0.1070 (2)0.0391 (7)
H10A0.32210.01110.09700.047*
H10B0.51300.00280.11440.047*
H10C0.40570.07960.05420.047*
C110.5679 (3)0.0119 (2)0.3103 (2)0.0385 (7)
H11A0.50280.06410.33190.046*
H11B0.64980.00750.35960.046*
H11C0.62070.03390.25730.046*
C120.4521 (3)0.1453 (2)0.44526 (19)0.0363 (7)
H12A0.44190.21110.46770.044*
H12B0.56360.12350.45920.044*
H12C0.38000.10290.47540.044*
C130.2156 (3)0.2923 (2)0.3241 (2)0.0330 (6)
H13A0.10030.27810.32140.040*
H13B0.23220.34780.28510.040*
H13C0.25760.30660.38760.040*
C140.1848 (3)0.2215 (2)0.1202 (2)0.0342 (7)
H14A0.07160.20770.12710.041*
H14B0.21230.19540.06160.041*
H14C0.20200.29110.12120.041*
C150.3889 (3)0.09274 (19)0.19184 (18)0.0270 (6)
C160.4616 (3)0.07218 (19)0.28264 (18)0.0261 (6)
C170.4078 (3)0.14293 (18)0.34352 (17)0.0242 (5)
C180.3024 (3)0.20706 (18)0.29068 (18)0.0240 (5)
C190.2896 (3)0.17594 (19)0.19755 (18)0.0269 (6)
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Fe0.01607 (19)0.0211 (2)0.0296 (2)0.00056 (14)0.00143 (13)0.00172 (17)
C10.0174 (12)0.0337 (16)0.0399 (16)0.0042 (11)0.0060 (10)0.0038 (13)
C20.0155 (12)0.0279 (15)0.0554 (18)0.0020 (11)0.0012 (11)0.0041 (14)
C30.0218 (13)0.0290 (16)0.0473 (18)0.0026 (11)0.0132 (12)0.0008 (13)
C3A0.0172 (12)0.0263 (14)0.0360 (15)0.0050 (10)0.0061 (10)0.0024 (11)
C40.0230 (13)0.0299 (15)0.0341 (15)0.0093 (11)0.0044 (10)0.0051 (12)
C50.0236 (13)0.0308 (15)0.0422 (17)0.0037 (11)0.0023 (11)0.0106 (13)
C60.0239 (13)0.0225 (14)0.0551 (19)0.0010 (11)0.0097 (12)0.0008 (13)
C70.0220 (13)0.0281 (15)0.0426 (16)0.0061 (11)0.0050 (11)0.0015 (13)
C7A0.0192 (12)0.0235 (14)0.0347 (15)0.0080 (10)0.0020 (10)0.0013 (12)
C80.0435 (17)0.0407 (19)0.0449 (19)0.0034 (14)0.0046 (14)0.0122 (15)
C90.0419 (16)0.0429 (18)0.0327 (16)0.0119 (13)0.0017 (12)0.0039 (14)
C100.0422 (16)0.0388 (18)0.0368 (17)0.0061 (13)0.0072 (12)0.0063 (14)
C110.0331 (15)0.0296 (16)0.0526 (19)0.0055 (12)0.0039 (13)0.0082 (14)
C120.0340 (15)0.0424 (18)0.0317 (16)0.0009 (13)0.0010 (11)0.0036 (13)
C130.0260 (13)0.0315 (15)0.0426 (17)0.0024 (12)0.0092 (11)0.0020 (14)
C140.0218 (13)0.0446 (18)0.0346 (15)0.0050 (12)0.0042 (11)0.0101 (13)
C150.0242 (13)0.0258 (14)0.0315 (14)0.0073 (10)0.0047 (10)0.0003 (12)
C160.0214 (12)0.0235 (14)0.0332 (15)0.0018 (10)0.0012 (10)0.0049 (11)
C170.0193 (12)0.0256 (14)0.0275 (14)0.0033 (10)0.0014 (10)0.0023 (11)
C180.0157 (11)0.0249 (13)0.0316 (14)0.0022 (10)0.0035 (10)0.0029 (12)
C190.0194 (12)0.0295 (15)0.0312 (15)0.0053 (10)0.0005 (10)0.0083 (11)
Geometric parameters (Å, º) top
Fe—C162.037 (3)C16—C171.432 (4)
Fe—C22.039 (2)C17—C181.425 (3)
Fe—C152.040 (3)C18—C191.425 (4)
Fe—C172.044 (3)C1—H10.9500
Fe—C32.045 (3)C2—H20.9500
Fe—C182.046 (2)C3—H30.9500
Fe—C192.049 (2)C5—H50.9500
Fe—C12.049 (3)C6—H60.9500
Fe—C3A2.089 (3)C8—H8A0.9800
Fe—C7A2.093 (3)C8—H8B0.9800
C1—C21.414 (4)C8—H8C0.9800
C1—C7A1.427 (4)C9—H9A0.9800
C2—C31.423 (4)C9—H9B0.9800
C3—C3A1.434 (4)C9—H9C0.9800
C3A—C41.429 (4)C10—H10A0.9800
C3A—C7A1.440 (4)C10—H10B0.9800
C4—C51.356 (4)C10—H10C0.9800
C4—C91.495 (4)C11—H11A0.9800
C5—C61.427 (4)C11—H11B0.9800
C6—C71.360 (4)C11—H11C0.9800
C7—C7A1.431 (4)C12—H12A0.9800
C7—C81.496 (4)C12—H12B0.9800
C10—C151.495 (4)C12—H12C0.9800
C11—C161.499 (4)C13—H13A0.9800
C12—C171.498 (4)C13—H13B0.9800
C13—C181.498 (4)C13—H13C0.9800
C14—C191.500 (4)C14—H14A0.9800
C15—C191.432 (4)C14—H14B0.9800
C15—C161.433 (4)C14—H14C0.9800
C16—Fe—C2106.44 (10)C17—C16—C15108.1 (2)
C16—Fe—C1541.15 (10)C17—C16—C11125.7 (2)
C2—Fe—C15122.00 (11)C15—C16—C11126.1 (2)
C16—Fe—C1741.08 (10)C17—C16—Fe69.70 (14)
C2—Fe—C17122.20 (11)C15—C16—Fe69.54 (14)
C15—Fe—C1769.18 (10)C11—C16—Fe128.98 (18)
C16—Fe—C3121.60 (11)C18—C17—C16108.0 (2)
C2—Fe—C340.76 (12)C18—C17—C12127.0 (2)
C15—Fe—C3106.33 (11)C16—C17—C12125.0 (2)
C17—Fe—C3158.12 (10)C18—C17—Fe69.69 (14)
C16—Fe—C1868.95 (10)C16—C17—Fe69.22 (14)
C2—Fe—C18158.69 (11)C12—C17—Fe128.19 (18)
C15—Fe—C1869.07 (10)C19—C18—C17108.1 (2)
C17—Fe—C1840.80 (10)C19—C18—C13124.2 (2)
C3—Fe—C18159.41 (11)C17—C18—C13127.7 (2)
C16—Fe—C1968.86 (10)C19—C18—Fe69.74 (14)
C2—Fe—C19158.85 (11)C17—C18—Fe69.51 (13)
C15—Fe—C1941.00 (10)C13—C18—Fe126.97 (18)
C17—Fe—C1968.64 (10)C18—C19—C15108.4 (2)
C3—Fe—C19122.85 (11)C18—C19—C14125.1 (2)
C18—Fe—C1940.73 (10)C15—C19—C14126.5 (3)
C16—Fe—C1122.06 (10)C18—C19—Fe69.54 (13)
C2—Fe—C140.46 (11)C15—C19—Fe69.20 (14)
C15—Fe—C1158.17 (11)C14—C19—Fe128.63 (18)
C17—Fe—C1107.19 (11)C2—C1—H1125.9
C3—Fe—C168.60 (12)C7A—C1—H1125.9
C18—Fe—C1123.10 (11)Fe—C1—H1124.8
C19—Fe—C1159.48 (11)C1—C2—H2125.6
C16—Fe—C3A158.47 (11)C3—C2—H2125.6
C2—Fe—C3A67.89 (11)Fe—C2—H2126.0
C15—Fe—C3A122.79 (11)C2—C3—H3126.2
C17—Fe—C3A159.61 (10)C3A—C3—H3126.2
C3—Fe—C3A40.57 (10)Fe—C3—H3124.7
C18—Fe—C3A123.89 (10)C4—C5—H5118.8
C19—Fe—C3A108.50 (10)C6—C5—H5118.8
C1—Fe—C3A68.01 (11)C7—C6—H6118.8
C16—Fe—C7A158.77 (10)C5—C6—H6118.8
C2—Fe—C7A67.67 (10)C7—C8—H8A109.5
C15—Fe—C7A159.41 (10)C7—C8—H8B109.5
C17—Fe—C7A123.35 (10)H8A—C8—H8B109.5
C3—Fe—C7A68.18 (11)C7—C8—H8C109.5
C18—Fe—C7A108.68 (10)H8A—C8—H8C109.5
C19—Fe—C7A124.01 (10)H8B—C8—H8C109.5
C1—Fe—C7A40.29 (10)C4—C9—H9A109.5
C3A—Fe—C7A40.29 (10)C4—C9—H9B109.5
C2—C1—C7A108.2 (3)H9A—C9—H9B109.5
C2—C1—Fe69.40 (15)C4—C9—H9C109.5
C7A—C1—Fe71.51 (14)H9A—C9—H9C109.5
C1—C2—C3108.9 (2)H9B—C9—H9C109.5
C1—C2—Fe70.14 (14)C15—C10—H10A109.5
C3—C2—Fe69.83 (14)C15—C10—H10B109.5
C2—C3—C3A107.6 (3)H10A—C10—H10B109.5
C2—C3—Fe69.40 (15)C15—C10—H10C109.5
C3A—C3—Fe71.36 (14)H10A—C10—H10C109.5
C4—C3A—C3132.0 (3)H10B—C10—H10C109.5
C4—C3A—C7A120.4 (2)C16—C11—H11A109.5
C3—C3A—C7A107.6 (2)C16—C11—H11B109.5
C4—C3A—Fe125.45 (17)H11A—C11—H11B109.5
C3—C3A—Fe68.06 (14)C16—C11—H11C109.5
C7A—C3A—Fe70.00 (15)H11A—C11—H11C109.5
C5—C4—C3A117.3 (3)H11B—C11—H11C109.5
C5—C4—C9123.0 (3)C17—C12—H12A109.5
C3A—C4—C9119.7 (3)C17—C12—H12B109.5
C4—C5—C6122.4 (3)H12A—C12—H12B109.5
C7—C6—C5122.5 (3)C17—C12—H12C109.5
C6—C7—C7A117.1 (3)H12A—C12—H12C109.5
C6—C7—C8123.4 (3)H12B—C12—H12C109.5
C7A—C7—C8119.5 (3)C18—C13—H13A109.5
C1—C7A—C7132.1 (3)C18—C13—H13B109.5
C1—C7A—C3A107.6 (2)H13A—C13—H13B109.5
C7—C7A—C3A120.3 (2)C18—C13—H13C109.5
C1—C7A—Fe68.19 (14)H13A—C13—H13C109.5
C7—C7A—Fe127.29 (17)H13B—C13—H13C109.5
C3A—C7A—Fe69.71 (14)C19—C14—H14A109.5
C19—C15—C16107.5 (2)C19—C14—H14B109.5
C19—C15—C10126.2 (2)H14A—C14—H14B109.5
C16—C15—C10126.3 (2)C19—C14—H14C109.5
C19—C15—Fe69.81 (15)H14A—C14—H14C109.5
C16—C15—Fe69.31 (14)H14B—C14—H14C109.5
C10—C15—Fe127.46 (18)
 

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