Di­carbonyl(η⁵-cyclo­penta­dienyl)(tri­methyl­silyl isocyanide)­iron(II) tri­fluoro­methane­sulfonate

In the title compound, [Fe(C₅H₅)(C₄H₉NSi)(CO)₂](CF₃SO₃), the Fe atom is coordinated by two carbonyl groups, a tri­methyl­silyl­isocyanide ligand and a cyclo­penta­dienyl ligand in a typical piano-stool structure. The Fe—CN, C[triple bond]N and CN—Si bond distances are 1.862 (4), 1.157 (6) and 1.794 (4) Å, respectively, and the Fe—C—N—Si arrangement is almost linear.

Key indicators

• Single-crystal X-ray study
• T = 153 K
• Mean [sigma](C-C) = 0.008 Å
• R factor = 0.068
• wR factor = 0.171
• Data-to-parameter ratio = 19.0

checkCIF/PLATON results

No syntax errors found



Alert level C
PLAT094_ALERT_2_C Ratio of Maximum / Minimum Residual Density ....       2.75
PLAT242_ALERT_2_C Check Low       Ueq as Compared to Neighbors for        Fe1
PLAT244_ALERT_4_C Low   'Solvent' Ueq as Compared to Neighbors for         S1
PLAT244_ALERT_4_C Low   'Solvent' Ueq as Compared to Neighbors for        C12
PLAT341_ALERT_3_C Low Bond Precision on C-C bonds (x 1000) Ang ...          8

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

   0 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

Data collection: CrystalClear (Rigaku, 2001); cell refinement: CrystalClear; data reduction: TEXSAN (Molecular Structure Corporation 2000); program(s) used to solve structure: DIRDIF94 (Beurskens et al., 1994); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEPII (Johnson, 1976); software used to prepare material for publication: TEXSAN.

Dicarbonyl(η⁵-cyclopentadienyl)(trimethylsilylisocyanide)iron(II) trifluoromethanesulfonate

Crystal data

[Fe(C5H5)(C4H9NSi)(CO)2](CF3SO3)	F(000) = 864.00
Mr = 425.23	Dx = 1.546 Mg m^−3
Monoclinic, P21/n	Mo Kα radiation, λ = 0.7107 Å
Hall symbol: -P 2yn	Cell parameters from 7143 reflections
a = 17.370 (5) Å	θ = 3.1–27.5°
b = 13.131 (4) Å	µ = 1.05 mm^−1
c = 8.011 (2) Å	T = 153 K
β = 91.803 (7)°	Block, yellow
V = 1826.4 (9) Å^3	0.30 × 0.13 × 0.10 mm
Z = 4

Data collection

Rigaku/MSC Mercury CCD diffractometer	3344 reflections with I > 2σ(I)
Detector resolution: 14.62 pixels mm^-1	Rint = 0.042
ω scans	θmax = 27.5°
Absorption correction: multi-scan (Jacobson, 1998)	h = −22→22
Tmin = 0.758, Tmax = 0.900	k = −14→17
17930 measured reflections	l = −10→10
4113 independent reflections

Refinement

Refinement on F^2	H-atom parameters constrained
R[F^2 > 2σ(F^2)] = 0.068	w = 1/[σ^2(Fo^2) + (0.0484P)^2 + 7.0396P] where P = (Fo^2 + 2Fc^2)/3
wR(F^2) = 0.171	(Δ/σ)max = 0.001
S = 1.16	Δρmax = 1.65 e Å^−3
4113 reflections	Δρmin = −0.60 e Å^−3
217 parameters

Special details

Refinement. Refinement was carried out using all reflections. The weighted R-factor (wR) and goodness of fit (S) are based on F². R-factor (gt) are based on F. The threshold expression of F² > 2.0 σ(F²) is used only for calculating R-factor (gt).

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Ų)

	x	y	z	Uiso*/Ueq
Fe1	0.64307 (4)	0.44959 (5)	0.72220 (8)	0.0219 (2)
S1	0.70694 (9)	0.1433 (1)	0.2504 (2)	0.0392 (3)
Si1	0.46863 (7)	0.1658 (1)	0.7336 (2)	0.0289 (3)
F1	0.6608 (3)	0.3320 (3)	0.2458 (6)	0.081 (1)
F2	0.5868 (3)	0.2328 (6)	0.3734 (6)	0.106 (2)
F3	0.5872 (3)	0.2291 (6)	0.1065 (6)	0.113 (2)
O1	0.5505 (3)	0.5886 (4)	0.9174 (9)	0.087 (2)
O2	0.5827 (3)	0.5220 (4)	0.3973 (6)	0.059 (1)
O3	0.7465 (3)	0.1639 (3)	0.1002 (5)	0.051 (1)
O4	0.7479 (3)	0.1672 (3)	0.4038 (6)	0.060 (1)
O5	0.6688 (4)	0.0472 (4)	0.2507 (6)	0.083 (2)
N1	0.5286 (2)	0.2771 (3)	0.7356 (5)	0.0261 (8)
C1	0.7485 (3)	0.5186 (4)	0.7783 (9)	0.044 (1)
C2	0.7311 (3)	0.4494 (5)	0.9057 (7)	0.044 (1)
C3	0.7257 (3)	0.3525 (4)	0.8342 (6)	0.033 (1)
C4	0.7382 (3)	0.3607 (4)	0.6628 (6)	0.030 (1)
C5	0.7535 (3)	0.4644 (5)	0.6291 (7)	0.038 (1)
C6	0.5860 (3)	0.5337 (4)	0.8423 (9)	0.051 (2)
C7	0.6056 (3)	0.4944 (4)	0.5246 (7)	0.037 (1)
C8	0.5716 (3)	0.3443 (3)	0.7314 (5)	0.0233 (9)
C9	0.5379 (4)	0.0596 (5)	0.7339 (9)	0.051 (2)
C10	0.4116 (4)	0.1725 (5)	0.9229 (9)	0.049 (2)
C11	0.4090 (3)	0.1766 (5)	0.5402 (9)	0.049 (2)
C12	0.6309 (4)	0.2376 (7)	0.2442 (7)	0.057 (2)
H1	0.7557	0.5897	0.7909	0.0443*
H2	0.7242	0.4656	1.0196	0.0437*
H3	0.7152	0.2912	0.8923	0.0327*
H4	0.7367	0.3066	0.5839	0.0301*
H5	0.7651	0.4923	0.5233	0.0383*
H6	0.5107	−0.0033	0.7332	0.0515*
H7	0.5681	0.0637	0.6374	0.0515*
H8	0.5704	0.0633	0.8311	0.0515*
H9	0.4452	0.1733	1.0188	0.0495*
H10	0.3814	0.2328	0.9205	0.0495*
H11	0.3787	0.1148	0.9276	0.0495*
H12	0.3796	0.2374	0.5429	0.0495*
H13	0.4414	0.1778	0.4468	0.0495*
H14	0.3754	0.1195	0.5311	0.0495*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
Fe1	0.0169 (3)	0.0183 (3)	0.0305 (4)	−0.0025 (2)	0.0017 (2)	−0.0011 (3)
S1	0.0637 (9)	0.0241 (6)	0.0295 (6)	−0.0115 (6)	−0.0026 (6)	0.0010 (5)
Si1	0.0195 (6)	0.0224 (6)	0.0450 (8)	−0.0055 (5)	0.0043 (5)	−0.0048 (6)
F1	0.118 (4)	0.055 (3)	0.071 (3)	0.043 (3)	0.022 (3)	0.009 (2)
F2	0.070 (3)	0.185 (6)	0.065 (3)	0.000 (4)	0.040 (2)	−0.003 (3)
F3	0.061 (3)	0.215 (7)	0.060 (3)	0.038 (4)	−0.023 (2)	−0.020 (4)
O1	0.070 (4)	0.064 (3)	0.128 (5)	−0.001 (3)	0.041 (3)	−0.051 (3)
O2	0.048 (3)	0.072 (3)	0.057 (3)	0.002 (2)	−0.012 (2)	0.032 (2)
O3	0.068 (3)	0.036 (2)	0.049 (2)	0.013 (2)	0.018 (2)	0.004 (2)
O4	0.088 (4)	0.043 (2)	0.048 (3)	0.010 (2)	−0.027 (2)	−0.005 (2)
O5	0.143 (5)	0.046 (3)	0.060 (3)	−0.056 (3)	−0.005 (3)	0.003 (2)
N1	0.018 (2)	0.029 (2)	0.031 (2)	−0.007 (2)	0.000 (1)	0.000 (2)
C1	0.022 (2)	0.032 (3)	0.079 (4)	−0.011 (2)	−0.002 (3)	−0.003 (3)
C2	0.045 (3)	0.057 (4)	0.029 (3)	−0.002 (3)	−0.011 (2)	−0.012 (3)
C3	0.026 (2)	0.035 (3)	0.037 (3)	0.000 (2)	−0.003 (2)	0.010 (2)
C4	0.021 (2)	0.039 (3)	0.030 (2)	0.006 (2)	−0.001 (2)	−0.002 (2)
C5	0.021 (2)	0.054 (3)	0.040 (3)	0.003 (2)	0.007 (2)	0.022 (3)
C6	0.035 (3)	0.035 (3)	0.083 (5)	−0.009 (2)	0.019 (3)	−0.025 (3)
C7	0.025 (2)	0.038 (3)	0.048 (3)	−0.002 (2)	0.001 (2)	0.015 (2)
C8	0.021 (2)	0.024 (2)	0.025 (2)	−0.002 (2)	0.001 (2)	−0.001 (2)
C9	0.043 (3)	0.030 (3)	0.081 (5)	0.005 (3)	0.003 (3)	−0.002 (3)
C10	0.041 (3)	0.044 (3)	0.066 (4)	−0.014 (3)	0.025 (3)	−0.005 (3)
C11	0.032 (3)	0.050 (3)	0.066 (4)	−0.006 (3)	−0.012 (3)	−0.017 (3)
C12	0.045 (3)	0.100 (6)	0.026 (3)	0.009 (4)	0.008 (2)	−0.001 (3)

Geometric parameters (Å, º)

Fe1—C1	2.079 (6)	N1—C8	1.157 (6)
Fe1—C2	2.088 (6)	C1—C2	1.406 (9)
Fe1—C3	2.099 (5)	C1—C5	1.396 (9)
Fe1—C4	2.090 (5)	C1—H1	0.947
Fe1—C5	2.088 (5)	C2—C3	1.398 (8)
Fe1—C6	1.786 (6)	C2—H2	0.948
Fe1—C7	1.791 (6)	C3—C4	1.401 (7)
Fe1—C8	1.862 (4)	C3—H3	0.950
S1—O3	1.430 (5)	C4—C5	1.414 (8)
S1—O4	1.436 (5)	C4—H4	0.951
S1—O5	1.426 (6)	C5—H5	0.951
S1—C12	1.810 (8)	C9—H6	0.951
Si1—N1	1.794 (4)	C9—H7	0.950
Si1—C9	1.842 (6)	C9—H8	0.950
Si1—C10	1.840 (7)	C10—H9	0.951
Si1—C11	1.842 (7)	C10—H10	0.949
F1—C12	1.343 (10)	C10—H11	0.951
F2—C12	1.309 (8)	C11—H12	0.948
F3—C12	1.325 (8)	C11—H13	0.950
O1—C6	1.134 (9)	C11—H14	0.951
O2—C7	1.143 (7)
F1···C2^i	3.391 (7)	O2···C6^ii	3.529 (8)
F1···C3^i	3.528 (7)	O3···C5^v	3.200 (7)
F3···N1^i	3.174 (6)	O3···C3^i	3.279 (7)
F3···C8^i	3.368 (7)	O3···C11^vi	3.560 (8)
F3···O1^ii	3.384 (9)	O3···C7^v	3.567 (7)
F3···C10^i	3.426 (8)	O3···C1^v	3.586 (8)
O1···O1^iii	3.22 (1)	O4···C1^vii	3.207 (8)
O1···C10^iii	3.443 (9)	O4···C2^vii	3.256 (8)
O1···C6^iii	3.492 (9)	O4···C10^vi	3.537 (8)
O2···C8^ii	3.339 (7)	O5···C2^vii	3.457 (8)
O2···C7^ii	3.355 (7)	O5···C10^viii	3.477 (8)
O2···O2^ii	3.404 (10)	O5···C5^v	3.539 (8)
O2···N1^ii	3.420 (6)	C3···C11^ix	3.562 (8)
O2···O3^iv	3.504 (7)
C1—Fe1—C2	39.4 (2)	Fe1—C2—H2	124.5
C1—Fe1—C3	65.6 (2)	C1—C2—C3	107.7 (5)
C1—Fe1—C4	66.1 (2)	C1—C2—H2	126.2
C1—Fe1—C5	39.2 (2)	C3—C2—H2	126.2
C1—Fe1—C6	96.5 (3)	Fe1—C3—C2	70.0 (3)
C1—Fe1—C7	109.9 (3)	Fe1—C3—C4	70.1 (3)
C1—Fe1—C8	154.0 (2)	Fe1—C3—H3	125.9
C2—Fe1—C3	39.0 (2)	C2—C3—C4	108.7 (5)
C2—Fe1—C4	66.0 (2)	C2—C3—H3	125.6
C2—Fe1—C5	65.9 (2)	C4—C3—H3	125.7
C2—Fe1—C6	91.6 (3)	Fe1—C4—C3	70.8 (3)
C2—Fe1—C7	149.3 (2)	Fe1—C4—C5	70.2 (3)
C2—Fe1—C8	116.5 (2)	Fe1—C4—H4	124.3
C3—Fe1—C4	39.1 (2)	C3—C4—C5	107.3 (5)
C3—Fe1—C5	65.6 (2)	C3—C4—H4	126.2
C3—Fe1—C6	121.9 (3)	C5—C4—H4	126.4
C3—Fe1—C7	143.2 (2)	Fe1—C5—C1	70.1 (3)
C3—Fe1—C8	88.8 (2)	Fe1—C5—C4	70.3 (3)
C4—Fe1—C5	39.6 (2)	Fe1—C5—H5	125.3
C4—Fe1—C6	157.6 (2)	C1—C5—C4	108.1 (5)
C4—Fe1—C7	104.5 (2)	C1—C5—H5	126.0
C4—Fe1—C8	97.3 (2)	C4—C5—H5	126.0
C5—Fe1—C6	131.8 (3)	Fe1—C6—O1	178.8 (6)
C5—Fe1—C7	88.1 (2)	Fe1—C7—O2	178.8 (5)
C5—Fe1—C8	134.8 (2)	Fe1—C8—N1	178.2 (4)
C6—Fe1—C7	94.6 (3)	Si1—C9—H6	109.5
C6—Fe1—C8	93.2 (2)	Si1—C9—H7	109.5
C7—Fe1—C8	93.1 (2)	Si1—C9—H8	109.5
O3—S1—O4	116.2 (3)	H6—C9—H7	109.4
O3—S1—O5	113.9 (3)	H6—C9—H8	109.4
O3—S1—C12	102.5 (3)	H7—C9—H8	109.5
O4—S1—O5	114.2 (3)	Si1—C10—H9	109.5
O4—S1—C12	102.4 (3)	Si1—C10—H10	109.6
O5—S1—C12	105.5 (4)	Si1—C10—H11	109.5
N1—Si1—C9	103.8 (2)	H9—C10—H10	109.5
N1—Si1—C10	106.3 (2)	H9—C10—H11	109.3
N1—Si1—C11	104.8 (2)	H10—C10—H11	109.5
C9—Si1—C10	113.8 (3)	Si1—C11—H12	109.5
C9—Si1—C11	114.1 (3)	Si1—C11—H13	109.4
C10—Si1—C11	112.8 (3)	Si1—C11—H14	109.4
Si1—N1—C8	174.7 (4)	H12—C11—H13	109.6
Fe1—C1—C2	70.6 (3)	H12—C11—H14	109.5
Fe1—C1—C5	70.8 (3)	H13—C11—H14	109.3
Fe1—C1—H1	124.4	S1—C12—F1	110.5 (5)
C2—C1—C5	108.2 (5)	S1—C12—F2	112.9 (6)
C2—C1—H1	126.2	S1—C12—F3	111.3 (6)
C5—C1—H1	125.6	F1—C12—F2	105.9 (6)
Fe1—C2—C1	70.0 (3)	F1—C12—F3	107.3 (6)
Fe1—C2—C3	71.0 (3)	F2—C12—F3	108.6 (5)
F1—C12—S1—O3	−61.4 (4)	F2—C12—S1—O5	60.8 (6)
F1—C12—S1—O4	59.4 (5)	F3—C12—S1—O3	57.8 (6)
F1—C12—S1—O5	179.2 (4)	F3—C12—S1—O4	178.5 (5)
F2—C12—S1—O3	−179.7 (5)	F3—C12—S1—O5	−61.7 (6)
F2—C12—S1—O4	−59.0 (6)

Symmetry codes: (i) x, y, z−1; (ii) −x+1, −y+1, −z+1; (iii) −x+1, −y+1, −z+2; (iv) −x+3/2, y+1/2, −z+1/2; (v) −x+3/2, y−1/2, −z+1/2; (vi) x+1/2, −y+1/2, z−1/2; (vii) −x+3/2, y−1/2, −z+3/2; (viii) −x+1, −y, −z+1; (ix) x+1/2, −y+1/2, z+1/2.