Methyl­chloro­sila­[1]­ferrocenophane

In the title compound, [Fe(C₁₁H₁₁ClSi)], the cyclo­penta­dienyl ligands are tilted towards the bridging Si atom, with a tilt angle of 19.4 (3)°.

Key indicators

• Single-crystal X-ray study
• T = 150 K
• Mean [sigma](C-C) = 0.007 Å
• R factor = 0.039
• wR factor = 0.098
• Data-to-parameter ratio = 16.2

checkCIF/PLATON results

No syntax errors found



Alert level C
ABSTM02_ALERT_3_C  The ratio of expected to reported Tmax/Tmin(RR') is < 0.90
            Tmin and Tmax reported:      0.585     0.783
            Tmin' and Tmax expected:      0.703     0.786
            RR' =      0.836
            Please check that your absorption correction is appropriate.
PLAT061_ALERT_3_C Tmax/Tmin Range Test RR' too Large .............       0.82
PLAT341_ALERT_3_C Low Bond Precision on C-C bonds (x 1000) Ang ...          7

Alert level G
REFLT03_ALERT_4_G Please check that the estimate of the number of Friedel pairs is
            correct. If it is not, please give the correct count in the
            _publ_section_exptl_refinement section of the submitted CIF.
           From the CIF: _diffrn_reflns_theta_max           27.52
           From the CIF: _reflns_number_total               2078
           Count of symmetry unique reflns         1237
           Completeness (_total/calc)            167.99%
           TEST3: Check Friedels for noncentro structure
           Estimate of Friedel pairs measured       841
           Fraction of Friedel pairs measured     0.680
           Are heavy atom types Z>Si present          yes

   0 ALERT level A = In general: serious problem
   0 ALERT level B = Potentially serious problem
   3 ALERT level C = Check and explain
   1 ALERT level G = General alerts; check

   0 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
   0 ALERT type 2 Indicator that the structure model may be wrong or deficient
   3 ALERT type 3 Indicator that the structure quality may be low
   1 ALERT type 4 Improvement, methodology, query or suggestion

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Computing details

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.

Methylchlorosila[1]ferrocenophane

Crystal data

[Fe(C11H11ClSi)]	F(000) = 536
Mr = 262.59	Dx = 1.626 Mg m^−3
Monoclinic, Cc	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: C -2yc	Cell parameters from 11776 reflections
a = 13.4146 (9) Å	θ = 2.6–27.5°
b = 10.2135 (8) Å	µ = 1.72 mm^−1
c = 7.8627 (6) Å	T = 150 K
β = 95.295 (5)°	Block, orange
V = 1072.67 (14) Å^3	0.20 × 0.18 × 0.14 mm
Z = 4

Data collection

Nonius KappaCCD diffractometer	2078 independent reflections
Radiation source: fine-focus sealed tube	1859 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.040
Detector resolution: 9 pixels mm^-1	θmax = 27.5°, θmin = 3.1°
φ scans and ω scans with κ offsets	h = −17→15
Absorption correction: multi-scan (SORTAV; Blessing 1995)	k = −12→13
Tmin = 0.585, Tmax = 0.783	l = −10→10
4024 measured reflections

Refinement

Refinement on F^2	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F^2 > 2σ(F^2)] = 0.039	H-atom parameters constrained
wR(F^2) = 0.098	w = 1/[σ^2(Fo^2) + (0.0418P)^2 + 2.256P] where P = (Fo^2 + 2Fc^2)/3
S = 1.05	(Δ/σ)max < 0.001
2078 reflections	Δρmax = 0.48 e Å^−3
128 parameters	Δρmin = −0.50 e Å^−3
2 restraints	Absolute structure: Flack (1983), 845 Friedel pairs
Primary atom site location: structure-invariant direct methods	Absolute structure parameter: −0.02 (2)

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.

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
Fe1	0.64830 (4)	0.22608 (6)	0.65546 (5)	0.0285 (2)
Cl1	0.92521 (10)	0.06896 (14)	0.59839 (18)	0.0473 (4)
Si1	0.82248 (9)	0.21381 (13)	0.52090 (16)	0.0316 (3)
C1	0.6999 (4)	0.1325 (4)	0.4558 (6)	0.0306 (10)
C2	0.6605 (3)	0.0403 (5)	0.5714 (6)	0.0335 (10)
H2A	0.7002	−0.0305	0.6340	0.040*
C3	0.5571 (4)	0.0668 (5)	0.5864 (6)	0.0347 (11)
H3A	0.5128	0.0194	0.6614	0.042*
C4	0.5298 (4)	0.1738 (6)	0.4797 (6)	0.0415 (13)
H4A	0.4625	0.2166	0.4677	0.050*
C5	0.6152 (4)	0.2168 (5)	0.3998 (6)	0.0364 (12)
H5A	0.6168	0.2920	0.3186	0.044*
C6	0.7848 (4)	0.3022 (5)	0.7134 (6)	0.0337 (10)
C7	0.7549 (4)	0.2259 (5)	0.8556 (6)	0.0298 (11)
H7A	0.7904	0.1467	0.9053	0.036*
C8	0.6650 (4)	0.2804 (5)	0.9105 (6)	0.0332 (11)
H8A	0.6262	0.2445	1.0026	0.040*
C9	0.6379 (4)	0.3911 (5)	0.8065 (6)	0.0373 (11)
H9A	0.5770	0.4467	0.8129	0.045*
C10	0.7112 (4)	0.4050 (5)	0.6856 (6)	0.0370 (11)
H10A	0.7107	0.4741	0.5953	0.044*
C11	0.8705 (4)	0.3170 (6)	0.3533 (7)	0.0459 (13)
H11A	0.9377	0.2875	0.3318	0.069*
H11B	0.8735	0.4084	0.3913	0.069*
H11C	0.8257	0.3099	0.2480	0.069*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
Fe1	0.0272 (3)	0.0308 (3)	0.0267 (3)	0.0016 (3)	−0.0015 (2)	−0.0030 (3)
Cl1	0.0372 (7)	0.0523 (8)	0.0515 (8)	0.0108 (6)	0.0004 (6)	0.0069 (7)
Si1	0.0268 (6)	0.0379 (7)	0.0303 (7)	−0.0003 (6)	0.0033 (5)	0.0035 (5)
C1	0.035 (2)	0.029 (2)	0.027 (2)	0.000 (2)	0.0022 (18)	−0.0052 (19)
C2	0.035 (2)	0.037 (3)	0.029 (2)	0.000 (2)	0.0016 (19)	−0.008 (2)
C3	0.029 (2)	0.043 (3)	0.032 (3)	−0.007 (2)	0.004 (2)	−0.009 (2)
C4	0.029 (2)	0.061 (4)	0.034 (3)	0.004 (3)	−0.004 (2)	−0.016 (3)
C5	0.034 (3)	0.044 (3)	0.029 (2)	0.001 (2)	−0.007 (2)	−0.002 (2)
C6	0.034 (2)	0.038 (3)	0.028 (2)	−0.006 (2)	−0.0053 (19)	0.0031 (19)
C7	0.033 (3)	0.031 (3)	0.024 (2)	−0.001 (2)	−0.0037 (18)	−0.0005 (18)
C8	0.034 (3)	0.038 (3)	0.028 (2)	0.001 (2)	0.002 (2)	−0.006 (2)
C9	0.039 (3)	0.037 (3)	0.033 (3)	0.008 (2)	−0.007 (2)	−0.009 (2)
C10	0.045 (3)	0.028 (2)	0.035 (2)	−0.005 (2)	−0.007 (2)	−0.0009 (19)
C11	0.044 (3)	0.053 (3)	0.042 (3)	−0.003 (3)	0.010 (2)	0.009 (3)

Geometric parameters (Å, º)

Fe1—C6	2.002 (5)	C2—H2A	1.0000
Fe1—C1	2.014 (4)	C3—C4	1.406 (8)
Fe1—C10	2.018 (5)	C3—H3A	1.0000
Fe1—C5	2.021 (5)	C4—C5	1.426 (8)
Fe1—C2	2.021 (5)	C4—H4A	1.0000
Fe1—C7	2.026 (5)	C5—H5A	1.0000
Fe1—C8	2.072 (5)	C6—C10	1.444 (7)
Fe1—C9	2.073 (5)	C6—C7	1.450 (7)
Fe1—C4	2.078 (5)	C7—C8	1.430 (7)
Fe1—C3	2.078 (5)	C7—H7A	1.0000
Fe1—Si1	2.6554 (13)	C8—C9	1.422 (7)
Cl1—Si1	2.0746 (18)	C8—H8A	1.0000
Si1—C11	1.849 (5)	C9—C10	1.436 (7)
Si1—C1	1.871 (5)	C9—H9A	1.0000
Si1—C6	1.872 (5)	C10—H10A	1.0000
C1—C2	1.442 (7)	C11—H11A	0.9800
C1—C5	1.461 (7)	C11—H11B	0.9800
C2—C3	1.429 (7)	C11—H11C	0.9800
C6—Fe1—C1	89.36 (19)	C2—C1—Si1	118.8 (3)
C6—Fe1—C10	42.1 (2)	C5—C1—Si1	117.4 (4)
C1—Fe1—C10	110.6 (2)	C2—C1—Fe1	69.3 (2)
C6—Fe1—C5	110.9 (2)	C5—C1—Fe1	69.0 (3)
C1—Fe1—C5	42.5 (2)	Si1—C1—Fe1	86.16 (18)
C10—Fe1—C5	102.1 (2)	C3—C2—C1	110.1 (4)
C6—Fe1—C2	109.8 (2)	C3—C2—Fe1	71.7 (3)
C1—Fe1—C2	41.89 (18)	C1—C2—Fe1	68.8 (3)
C10—Fe1—C2	147.5 (2)	C3—C2—H2A	125.0
C5—Fe1—C2	69.4 (2)	C1—C2—H2A	125.0
C6—Fe1—C7	42.18 (19)	Fe1—C2—H2A	125.0
C1—Fe1—C7	109.7 (2)	C4—C3—C2	107.4 (4)
C10—Fe1—C7	69.6 (2)	C4—C3—Fe1	70.2 (3)
C5—Fe1—C7	147.9 (2)	C2—C3—Fe1	67.5 (3)
C2—Fe1—C7	100.41 (19)	C4—C3—H3A	126.3
C6—Fe1—C8	70.19 (19)	C2—C3—H3A	126.3
C1—Fe1—C8	150.1 (2)	Fe1—C3—H3A	126.3
C10—Fe1—C8	68.7 (2)	C3—C4—C5	109.1 (4)
C5—Fe1—C8	165.8 (2)	C3—C4—Fe1	70.2 (3)
C2—Fe1—C8	124.3 (2)	C5—C4—Fe1	67.5 (3)
C7—Fe1—C8	40.8 (2)	C3—C4—H4A	125.4
C6—Fe1—C9	70.3 (2)	C5—C4—H4A	125.4
C1—Fe1—C9	151.39 (19)	Fe1—C4—H4A	125.4
C10—Fe1—C9	41.1 (2)	C4—C5—C1	108.6 (5)
C5—Fe1—C9	126.0 (2)	C4—C5—Fe1	71.8 (3)
C2—Fe1—C9	164.18 (19)	C1—C5—Fe1	68.5 (3)
C7—Fe1—C9	68.64 (19)	C4—C5—H5A	125.7
C8—Fe1—C9	40.1 (2)	C1—C5—H5A	125.7
C6—Fe1—C4	151.4 (2)	Fe1—C5—H5A	125.7
C1—Fe1—C4	69.9 (2)	C10—C6—C7	105.9 (4)
C10—Fe1—C4	126.6 (2)	C10—C6—Si1	117.4 (3)
C5—Fe1—C4	40.7 (2)	C7—C6—Si1	118.6 (4)
C2—Fe1—C4	67.7 (2)	C10—C6—Fe1	69.5 (3)
C7—Fe1—C4	163.4 (2)	C7—C6—Fe1	69.8 (3)
C8—Fe1—C4	136.07 (19)	Si1—C6—Fe1	86.5 (2)
C9—Fe1—C4	120.1 (2)	C8—C7—C6	108.9 (4)
C6—Fe1—C3	150.2 (2)	C8—C7—Fe1	71.3 (3)
C1—Fe1—C3	70.19 (19)	C6—C7—Fe1	68.0 (3)
C10—Fe1—C3	165.9 (2)	C8—C7—H7A	125.5
C5—Fe1—C3	68.5 (2)	C6—C7—H7A	125.5
C2—Fe1—C3	40.77 (19)	Fe1—C7—H7A	125.5
C7—Fe1—C3	124.0 (2)	C9—C8—C7	108.3 (4)
C8—Fe1—C3	118.1 (2)	C9—C8—Fe1	70.0 (3)
C9—Fe1—C3	135.8 (2)	C7—C8—Fe1	67.8 (3)
C4—Fe1—C3	39.6 (2)	C9—C8—H8A	125.8
C6—Fe1—Si1	44.71 (14)	C7—C8—H8A	125.8
C1—Fe1—Si1	44.67 (14)	Fe1—C8—H8A	125.8
C10—Fe1—Si1	73.49 (15)	C8—C9—C10	107.8 (4)
C5—Fe1—Si1	73.86 (15)	C8—C9—Fe1	69.9 (3)
C2—Fe1—Si1	74.01 (13)	C10—C9—Fe1	67.4 (3)
C7—Fe1—Si1	74.07 (14)	C8—C9—H9A	126.1
C8—Fe1—Si1	112.18 (14)	C10—C9—H9A	126.1
C9—Fe1—Si1	111.99 (15)	Fe1—C9—H9A	126.1
C4—Fe1—Si1	111.73 (14)	C9—C10—C6	109.1 (4)
C3—Fe1—Si1	112.18 (13)	C9—C10—Fe1	71.5 (3)
C11—Si1—C1	114.4 (2)	C6—C10—Fe1	68.4 (3)
C11—Si1—C6	116.0 (3)	C9—C10—H10A	125.4
C1—Si1—C6	98.0 (2)	C6—C10—H10A	125.4
C11—Si1—Cl1	110.5 (2)	Fe1—C10—H10A	125.4
C1—Si1—Cl1	107.90 (16)	Si1—C11—H11A	109.5
C6—Si1—Cl1	109.18 (16)	Si1—C11—H11B	109.5
C11—Si1—Fe1	129.3 (2)	H11A—C11—H11B	109.5
C1—Si1—Fe1	49.17 (13)	Si1—C11—H11C	109.5
C6—Si1—Fe1	48.82 (15)	H11A—C11—H11C	109.5
Cl1—Si1—Fe1	120.11 (7)	H11B—C11—H11C	109.5
C2—C1—C5	104.8 (4)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
C9—H9A···Cl1^i	1.00	2.81	3.641 (5)	141

Symmetry code: (i) x−1/2, y+1/2, z.