(η⁵-Penta­methyl­cyclo­penta­dienyl)(η⁵-5,6,7-tri­hydro-4,8-di­methyl-s-indacenyl)­iron(II)

In the title compound, [Fe(C₁₀H₁₅)(C₁₄H₁₅)], the coordinating rings make an angle of 3.4 (2)° with each other and are rotated away from the ideal eclipsed conformation by ca 13°.

Key indicators

• Single-crystal X-ray study
• T = 178 K
• Mean [sigma](C-C) = 0.004 Å
• R factor = 0.038
• wR factor = 0.103
• Data-to-parameter ratio = 14.4

checkCIF results

No syntax errors found

ADDSYM reports no extra symmetry


 Alert Level B:



ABSTM_02  Alert B The ratio of Tmax/Tmin expected RT(exp) is > 1.20
          Absorption corrections should be applied.
          Tmin and Tmax expected:      0.734     0.887
          RT(exp) =      1.209


 0 Alert Level A = Potentially serious problem

 1 Alert Level B = Potential problem

 0 Alert Level C = Please check

---

Computing details

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

(2)

Crystal data

[Fe(C10H15)(C14H15)]	Z = 2
Mr = 374.33	F(000) = 400
Triclinic, P1	Dx = 1.307 Mg m^−3
a = 8.6838 (15) Å	Mo Kα radiation, λ = 0.71073 Å
b = 9.713 (2) Å	Cell parameters from 50 reflections
c = 11.566 (3) Å	θ = 10–11.5°
α = 80.62 (2)°	µ = 0.80 mm^−1
β = 81.09 (2)°	T = 178 K
γ = 88.82 (2)°	Tablet, red
V = 950.9 (4) Å^3	0.40 × 0.40 × 0.15 mm

Data collection

Nicolet R3 diffractometer	Rint = 0.017
Radiation source: fine-focus sealed tube	θmax = 25.0°, θmin = 3.0°
Graphite monochromator	h = −10→10
ω scans	k = 0→11
3561 measured reflections	l = −13→13
3346 independent reflections	3 standard reflections every 147 reflections
2889 reflections with I > 2σ(I)	intensity decay: none

Refinement

Refinement on F^2	Primary atom site location: isostructural to Ru analogue
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F^2 > 2σ(F^2)] = 0.038	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.103	H-atom parameters constrained
S = 1.08	w = 1/[σ^2(Fo^2) + (0.0604P)^2 + 0.467P] where P = (Fo^2 + 2Fc^2)/3
3346 reflections	(Δ/σ)max = 0.004
233 parameters	Δρmax = 0.60 e Å^−3
0 restraints	Δρmin = −0.63 e Å^−3

Special details

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)

0.2522 (0.0056) x + 6.6850 (0.0049) y - 6.8551 (0.0057) z = 1.7381 (0.0027)

* -0.0097 (0.0018) C1 * 0.0277 (0.0019) C2 * -0.0085 (0.0018) C3 * -0.0101 (0.0020) C3A * -0.0072 (0.0017) C4 * 0.0129 (0.0018) C4A * 0.0086 (0.0018) C7A * -0.0050 (0.0018) C8 * -0.0085 (0.0020) C8A -1.6745 (0.0012) Fe

Rms deviation of fitted atoms = 0.0126

- 0.5392 (0.0100) x - 7.0151 (0.0083) y + 6.3364 (0.0116) z = 1.3638 (0.0045)

Angle to previous plane (with approximate e.s.d.) = 3.36 (0.15)

* 0.0024 (0.0014) C11 * -0.0016 (0.0014) C12 * 0.0001 (0.0014) C13 * 0.0014 (0.0014) C14 * -0.0024 (0.0014) C15 - 1.6426 (0.0012) Fe

Rms deviation of fitted atoms = 0.0018

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 (Ų)

	x	y	z	Uiso*/Ueq
Fe	0.15828 (4)	0.20522 (3)	0.19668 (3)	0.01985 (13)
C1	0.0520 (3)	0.3807 (2)	0.1210 (2)	0.0264 (5)
H1	−0.0535	0.4050	0.1440	0.032*
C2	0.1064 (3)	0.2955 (3)	0.0345 (2)	0.0288 (6)
H2	0.0438	0.2562	−0.0123	0.035*
C3	0.2702 (3)	0.2791 (2)	0.0298 (2)	0.0254 (5)
H3	0.3352	0.2241	−0.0185	0.030*
C3A	0.3204 (3)	0.3599 (2)	0.1107 (2)	0.0208 (5)
C4	0.4720 (3)	0.3835 (2)	0.1388 (2)	0.0209 (5)
C4A	0.4784 (3)	0.4695 (2)	0.2200 (2)	0.0229 (5)
C5	0.6209 (3)	0.5156 (3)	0.2644 (2)	0.0312 (6)
H5A	0.7083	0.5388	0.1984	0.037*
H5B	0.6549	0.4420	0.3249	0.037*
C6	0.5651 (3)	0.6456 (3)	0.3185 (3)	0.0368 (6)
H6A	0.6213	0.6558	0.3848	0.044*
H6B	0.5821	0.7308	0.2580	0.044*
C7	0.3904 (3)	0.6204 (3)	0.3629 (2)	0.0317 (6)
H7A	0.3725	0.5695	0.4453	0.038*
H7B	0.3327	0.7096	0.3596	0.038*
C7A	0.3415 (3)	0.5326 (2)	0.2771 (2)	0.0233 (5)
C8	0.1959 (3)	0.5121 (2)	0.2538 (2)	0.0234 (5)
C8A	0.1829 (3)	0.4235 (2)	0.1674 (2)	0.0208 (5)
C9	0.0508 (3)	0.5770 (3)	0.3116 (3)	0.0343 (6)
H9A	0.0801	0.6457	0.3578	0.041*
H9B	−0.0143	0.5042	0.3642	0.041*
H9C	−0.0076	0.6233	0.2503	0.041*
C10	0.6121 (3)	0.3171 (3)	0.0769 (2)	0.0303 (6)
H10A	0.6327	0.3611	−0.0065	0.036*
H10B	0.5922	0.2172	0.0817	0.036*
H10C	0.7028	0.3296	0.1151	0.036*
C11	0.2687 (3)	0.0573 (2)	0.3020 (2)	0.0224 (5)
C12	0.1876 (3)	−0.0054 (2)	0.2249 (2)	0.0223 (5)
C13	0.0261 (3)	0.0287 (2)	0.2493 (2)	0.0231 (5)
C14	0.0071 (3)	0.1134 (2)	0.3416 (2)	0.0242 (5)
C15	0.1575 (3)	0.1311 (2)	0.3734 (2)	0.0244 (5)
C16	0.4390 (3)	0.0443 (3)	0.3120 (3)	0.0339 (6)
H16A	0.4528	−0.0255	0.3810	0.041*
H16B	0.4793	0.1346	0.3215	0.041*
H16C	0.4959	0.0152	0.2400	0.041*
C17	0.2599 (3)	−0.0923 (3)	0.1339 (2)	0.0305 (6)
H17A	0.3688	−0.0639	0.1065	0.037*
H17B	0.2023	−0.0783	0.0665	0.037*
H17C	0.2555	−0.1911	0.1697	0.037*
C18	−0.1015 (3)	−0.0197 (3)	0.1914 (2)	0.0333 (6)
H18A	−0.0596	−0.0316	0.1100	0.040*
H18B	−0.1849	0.0498	0.1903	0.040*
H18C	−0.1433	−0.1090	0.2362	0.040*
C19	−0.1437 (3)	0.1703 (3)	0.3965 (2)	0.0357 (6)
H19A	−0.1865	0.1064	0.4685	0.043*
H19B	−0.2180	0.1797	0.3400	0.043*
H19C	−0.1252	0.2619	0.4170	0.043*
C20	0.1932 (4)	0.2107 (3)	0.4668 (2)	0.0360 (6)
H20A	0.1111	0.2793	0.4809	0.043*
H20B	0.2936	0.2588	0.4401	0.043*
H20C	0.1984	0.1458	0.5405	0.043*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
Fe	0.0243 (2)	0.01526 (19)	0.0198 (2)	0.00052 (13)	−0.00173 (13)	−0.00380 (13)
C1	0.0268 (13)	0.0192 (12)	0.0319 (13)	0.0025 (10)	−0.0063 (10)	0.0010 (10)
C2	0.0416 (15)	0.0233 (12)	0.0227 (12)	−0.0048 (11)	−0.0118 (11)	−0.0003 (10)
C3	0.0345 (14)	0.0220 (12)	0.0186 (12)	−0.0009 (10)	0.0000 (10)	−0.0038 (10)
C3A	0.0263 (12)	0.0146 (11)	0.0197 (11)	0.0000 (9)	0.0009 (9)	−0.0017 (9)
C4	0.0221 (11)	0.0165 (11)	0.0216 (11)	0.0017 (9)	0.0009 (9)	0.0002 (9)
C4A	0.0252 (12)	0.0182 (11)	0.0244 (12)	0.0005 (9)	−0.0023 (10)	−0.0019 (9)
C5	0.0307 (14)	0.0284 (14)	0.0362 (15)	−0.0011 (11)	−0.0100 (11)	−0.0057 (11)
C6	0.0418 (16)	0.0316 (15)	0.0420 (16)	−0.0055 (12)	−0.0134 (13)	−0.0135 (12)
C7	0.0440 (16)	0.0275 (13)	0.0261 (13)	−0.0008 (11)	−0.0061 (11)	−0.0110 (11)
C7A	0.0324 (13)	0.0168 (11)	0.0195 (12)	0.0004 (10)	−0.0005 (10)	−0.0028 (9)
C8	0.0262 (12)	0.0151 (11)	0.0265 (12)	0.0034 (9)	0.0022 (10)	−0.0024 (9)
C8A	0.0244 (12)	0.0139 (11)	0.0225 (12)	0.0023 (9)	−0.0013 (9)	−0.0005 (9)
C9	0.0320 (14)	0.0264 (14)	0.0432 (16)	0.0029 (11)	0.0064 (12)	−0.0131 (12)
C10	0.0269 (13)	0.0262 (13)	0.0357 (14)	0.0043 (10)	0.0042 (11)	−0.0079 (11)
C11	0.0273 (12)	0.0170 (11)	0.0212 (12)	0.0017 (9)	−0.0030 (10)	0.0009 (9)
C12	0.0300 (13)	0.0162 (11)	0.0206 (12)	0.0021 (9)	−0.0026 (10)	−0.0042 (9)
C13	0.0275 (12)	0.0165 (11)	0.0246 (12)	−0.0025 (9)	−0.0037 (10)	−0.0012 (9)
C14	0.0292 (13)	0.0175 (11)	0.0220 (12)	0.0005 (10)	0.0039 (10)	0.0005 (9)
C15	0.0379 (14)	0.0157 (11)	0.0186 (12)	−0.0018 (10)	−0.0029 (10)	−0.0013 (9)
C16	0.0311 (14)	0.0312 (14)	0.0386 (15)	0.0016 (11)	−0.0095 (12)	0.0009 (12)
C17	0.0428 (15)	0.0216 (12)	0.0266 (13)	0.0066 (11)	−0.0005 (11)	−0.0074 (10)
C18	0.0342 (14)	0.0292 (14)	0.0381 (15)	−0.0054 (11)	−0.0099 (12)	−0.0053 (12)
C19	0.0350 (15)	0.0286 (14)	0.0376 (15)	0.0062 (11)	0.0106 (12)	−0.0038 (12)
C20	0.0599 (19)	0.0274 (14)	0.0224 (13)	−0.0038 (13)	−0.0075 (12)	−0.0071 (11)

Geometric parameters (Å, º)

Fe—C12	2.036 (2)	C8—C8A	1.439 (3)
Fe—C13	2.037 (2)	C8—C9	1.508 (3)
Fe—C3	2.045 (2)	C9—H9A	0.980
Fe—C2	2.049 (2)	C9—H9B	0.980
Fe—C11	2.049 (2)	C9—H9C	0.980
Fe—C14	2.051 (2)	C10—H10A	0.980
Fe—C15	2.053 (2)	C10—H10B	0.980
Fe—C1	2.054 (2)	C10—H10C	0.980
Fe—C3A	2.096 (2)	C11—C15	1.431 (3)
Fe—C8A	2.102 (2)	C11—C12	1.432 (3)
C1—C2	1.419 (4)	C11—C16	1.502 (3)
C1—C8A	1.426 (3)	C12—C13	1.430 (3)
C1—H1	0.950	C12—C17	1.509 (3)
C2—C3	1.422 (4)	C13—C14	1.439 (3)
C2—H2	0.950	C13—C18	1.500 (3)
C3—C3A	1.436 (3)	C14—C15	1.432 (4)
C3—H3	0.950	C14—C19	1.500 (3)
C3A—C4	1.436 (3)	C15—C20	1.498 (3)
C3A—C8A	1.448 (3)	C16—H16A	0.980
C4—C4A	1.362 (3)	C16—H16B	0.980
C4—C10	1.503 (3)	C16—H16C	0.980
C4A—C7A	1.443 (3)	C17—H17A	0.980
C4A—C5	1.514 (3)	C17—H17B	0.980
C5—C6	1.536 (4)	C17—H17C	0.980
C5—H5A	0.990	C18—H18A	0.980
C5—H5B	0.990	C18—H18B	0.980
C6—C7	1.536 (4)	C18—H18C	0.980
C6—H6A	0.990	C19—H19A	0.980
C6—H6B	0.990	C19—H19B	0.980
C7—C7A	1.521 (3)	C19—H19C	0.980
C7—H7A	0.990	C20—H20A	0.980
C7—H7B	0.990	C20—H20B	0.980
C7A—C8	1.358 (3)	C20—H20C	0.980
C12—Fe—C13	41.11 (10)	C6—C7—H7A	111.1
C12—Fe—C3	107.24 (10)	C7A—C7—H7B	111.1
C13—Fe—C3	127.32 (10)	C6—C7—H7B	111.1
C12—Fe—C2	117.46 (10)	H7A—C7—H7B	109.1
C13—Fe—C2	107.14 (10)	C8—C7A—C4A	122.8 (2)
C3—Fe—C2	40.64 (10)	C8—C7A—C7	128.3 (2)
C12—Fe—C11	41.03 (9)	C4A—C7A—C7	108.9 (2)
C13—Fe—C11	69.03 (10)	C7A—C8—C8A	116.7 (2)
C3—Fe—C11	118.08 (10)	C7A—C8—C9	124.1 (2)
C2—Fe—C11	151.64 (10)	C8A—C8—C9	119.2 (2)
C12—Fe—C14	69.21 (9)	C1—C8A—C8	132.0 (2)
C13—Fe—C14	41.20 (10)	C1—C8A—C3A	107.7 (2)
C3—Fe—C14	165.83 (10)	C8—C8A—C3A	120.3 (2)
C2—Fe—C14	127.75 (11)	C1—C8A—Fe	68.14 (13)
C11—Fe—C14	68.86 (10)	C8—C8A—Fe	127.57 (16)
C12—Fe—C15	69.02 (9)	C3A—C8A—Fe	69.62 (12)
C13—Fe—C15	69.03 (10)	C8—C9—H9A	109.5
C3—Fe—C15	152.07 (11)	C8—C9—H9B	109.5
C2—Fe—C15	166.15 (10)	H9A—C9—H9B	109.5
C11—Fe—C15	40.83 (10)	C8—C9—H9C	109.5
C14—Fe—C15	40.83 (10)	H9A—C9—H9C	109.5
C12—Fe—C1	151.02 (10)	H9B—C9—H9C	109.5
C13—Fe—C1	117.31 (10)	C4—C10—H10A	109.5
C3—Fe—C1	68.47 (10)	C4—C10—H10B	109.5
C2—Fe—C1	40.46 (10)	H10A—C10—H10B	109.5
C11—Fe—C1	166.75 (10)	C4—C10—H10C	109.5
C14—Fe—C1	107.59 (10)	H10A—C10—H10C	109.5
C15—Fe—C1	128.36 (10)	H10B—C10—H10C	109.5
C12—Fe—C3A	128.36 (9)	C15—C11—C12	108.0 (2)
C13—Fe—C3A	166.06 (9)	C15—C11—C16	124.9 (2)
C3—Fe—C3A	40.55 (9)	C12—C11—C16	127.0 (2)
C2—Fe—C3A	67.85 (10)	C15—C11—Fe	69.70 (13)
C11—Fe—C3A	108.78 (9)	C12—C11—Fe	68.97 (13)
C14—Fe—C3A	152.07 (10)	C16—C11—Fe	129.04 (17)
C15—Fe—C3A	118.94 (10)	C13—C12—C11	108.0 (2)
C1—Fe—C3A	67.99 (10)	C13—C12—C17	126.0 (2)
C12—Fe—C8A	166.97 (9)	C11—C12—C17	126.0 (2)
C13—Fe—C8A	151.37 (10)	C13—C12—Fe	69.51 (13)
C3—Fe—C8A	68.05 (9)	C11—C12—Fe	70.00 (13)
C2—Fe—C8A	67.51 (10)	C17—C12—Fe	126.05 (17)
C11—Fe—C8A	129.27 (9)	C12—C13—C14	108.0 (2)
C14—Fe—C8A	118.36 (9)	C12—C13—C18	125.8 (2)
C15—Fe—C8A	109.06 (9)	C14—C13—C18	126.1 (2)
C1—Fe—C8A	40.12 (9)	C12—C13—Fe	69.38 (13)
C3A—Fe—C8A	40.34 (9)	C14—C13—Fe	69.92 (13)
C2—C1—C8A	108.3 (2)	C18—C13—Fe	127.86 (17)
C2—C1—Fe	69.57 (14)	C15—C14—C13	107.7 (2)
C8A—C1—Fe	71.73 (13)	C15—C14—C19	126.1 (2)
C2—C1—H1	125.8	C13—C14—C19	126.2 (2)
C8A—C1—H1	125.8	C15—C14—Fe	69.63 (13)
Fe—C1—H1	124.5	C13—C14—Fe	68.88 (13)
C1—C2—C3	108.5 (2)	C19—C14—Fe	127.89 (17)
C1—C2—Fe	69.96 (14)	C11—C15—C14	108.2 (2)
C3—C2—Fe	69.52 (14)	C11—C15—C20	125.5 (2)
C1—C2—H2	125.7	C14—C15—C20	126.3 (2)
C3—C2—H2	125.7	C11—C15—Fe	69.47 (13)
Fe—C2—H2	126.4	C14—C15—Fe	69.54 (13)
C2—C3—C3A	108.1 (2)	C20—C15—Fe	127.50 (17)
C2—C3—Fe	69.84 (14)	C11—C16—H16A	109.5
C3A—C3—Fe	71.65 (13)	C11—C16—H16B	109.5
C2—C3—H3	125.9	H16A—C16—H16B	109.5
C3A—C3—H3	125.9	C11—C16—H16C	109.5
Fe—C3—H3	124.2	H16A—C16—H16C	109.5
C3—C3A—C4	131.7 (2)	H16B—C16—H16C	109.5
C3—C3A—C8A	107.2 (2)	C12—C17—H17A	109.5
C4—C3A—C8A	121.1 (2)	C12—C17—H17B	109.5
C3—C3A—Fe	67.80 (13)	H17A—C17—H17B	109.5
C4—C3A—Fe	127.49 (16)	C12—C17—H17C	109.5
C8A—C3A—Fe	70.03 (13)	H17A—C17—H17C	109.5
C4A—C4—C3A	116.3 (2)	H17B—C17—H17C	109.5
C4A—C4—C10	124.2 (2)	C13—C18—H18A	109.5
C3A—C4—C10	119.5 (2)	C13—C18—H18B	109.5
C4—C4A—C7A	122.7 (2)	H18A—C18—H18B	109.5
C4—C4A—C5	128.0 (2)	C13—C18—H18C	109.5
C7A—C4A—C5	109.3 (2)	H18A—C18—H18C	109.5
C4A—C5—C6	103.6 (2)	H18B—C18—H18C	109.5
C4A—C5—H5A	111.0	C14—C19—H19A	109.5
C6—C5—H5A	111.0	C14—C19—H19B	109.5
C4A—C5—H5B	111.0	H19A—C19—H19B	109.5
C6—C5—H5B	111.0	C14—C19—H19C	109.5
H5A—C5—H5B	109.0	H19A—C19—H19C	109.5
C7—C6—C5	104.9 (2)	H19B—C19—H19C	109.5
C7—C6—H6A	110.8	C15—C20—H20A	109.5
C5—C6—H6A	110.8	C15—C20—H20B	109.5
C7—C6—H6B	110.8	H20A—C20—H20B	109.5
C5—C6—H6B	110.8	C15—C20—H20C	109.5
H6A—C6—H6B	108.8	H20A—C20—H20C	109.5
C7A—C7—C6	103.3 (2)	H20B—C20—H20C	109.5
C7A—C7—H7A	111.1