(η5-Cyclo­penta­dienyl)(p-fluoro­phenoxo)(nitro­syl)(tri­methyl­silyl­methyl)­molybdenum(II)

Hayton, T.W.; Legzdins, P.; Rettig, S.J.

doi:10.1107/S0108270101019382

(η⁵-Cyclopentadienyl)(p-fluorophenoxo)(nitrosyl)(trimethylsilylmethyl)molybdenum(II)

T. W. Hayton, P. Legzdins and S. J. Rettig

The title complex, [Mo(C₅H₅)(C₆H₄FO)(C₄H₁₁Si)(NO)], is formed by reacting CpMo(NO)(CH₂SiMe₃)₂, where Cp is cyclopentadienyl, with one equivalent of p-FC₆H₄OH. The complex exhibits the expected piano-stool molecular structure, with a linear nitrosyl ligand [Mo—N—O 168.2 (2)°] having Mo—N and N—O distances of 1.764 (2) and 1.207 (3) Å, respectively. The phenoxo Mo—O distance of 1.945 (2) Å is suggestive of some multiple-bond character.

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Supporting information

	Crystallographic Information File (CIF) https://doi.org/10.1107/S0108270101019382/da1210sup1.cif Contains datablocks global, I
	Structure factor file (CIF format) https://doi.org/10.1107/S0108270101019382/da1210Isup2.hkl Contains datablock I

CCDC reference: 181977

Comment top

Many attempts to generate molybdenum– and tungsten–alkoxo complexes in our laboratories have been unsuccessful. The standard metathetical protocol, using a metal–halide precursor with an alkali metal–alkoxide salt, often results in either decomposition or the formation of N—O bond-cleavage products (Legzdins et al., 1996). An alternate procedure, namely protonation of the alkyl ligand in CpMo(NO)(CH₂SiMe₃)₂ by an alcohol to generate the corresponding alkoxo complex and SiMe₄, has now been found to generate a variety of new complexes in good yield. The title compound, CpMo(NO)(CH₂SiMe₃)(p-FC₆H₄O), (I) (Fig. 1), has been synthesized by this method.

Compound (I) exhibits a pseudo-tetrahedral geometry around the Mo atom typical of this class of three-legged piano-stool molecules. The Mo—N—O linkage is linear [Mo1—N1—O1 168.2 (3)°], with a short Mo1—N1 distance [1.764 (2) Å] and a long N—O distance [1.207 (3) Å], relative to most other nitrosyls (Feltham & Enemark, 1981). This indicates that the nitrosyl ligand is strongly involved in π-back-bonding with the Mo centre. The phenoxo Mo—O distance is 1.945 (2) Å, significantly longer than the W—O distances in the related complexes Cp*W(NO)(OCH₂Ph)₂ [1.910 (4) Å] and Cp*W(NO)(OCMe₃)₂ [Cp* is pentamethylcyclopentadienyl; 1.890 (5) and 1.903 (5) Å, respectively; Legzdins et al., 1993], where the metal–oxygen bond has definite multiple-bond character. However, it is shorter than the W—O bonds in Cp*W(NO)(OMe)[η²-O═C(Me)CH═CPh] [2.001 (7) Å; Legzdins et al., 1998] and Cp*W(NO)(OCMe₃)[η²-N(CMe₃)═C(CH₂CMe₃)] [1.978 (4) Å; Legzdins et al., 1994]. The W—O bonds in these two compounds, by the nature of the η²-bound co-ligands, are single bonds, which then suggests that the Mo—O link in (I) is somewhat more than a single bond. Comparison to other W and Mo complexes, namely Cp*W(MeCCMe)₂(OPh) [W—O 2.072 (7) Å; O'Regan et al., 1992], [Cp*W(Me)₂(OC₆F₅)]₂(µ-N₂) [W—O 2.079 (8) Å; O'Regan et al., 1990], and [Mo₂(OPh-4-Me)₇(Me₂NH)₂]^- [Mo—O_terminal 2.03 Å (average); Coffindaffer et al., 1985], further supports this assumption.

Experimental top

In a Schlenk tube, under anaerobic and anhydrous conditions, (η⁵-C₅H₅)Mo(NO)(CH₂SiMe₃)₂ (100 mg, 0.27 mmol) was combined with p-fluorophenol (31 mg, 0.27 mmol), and the mixture was dissolved in THF (20 ml). The resulting purple solution was stirred for 3 days at room temperature, whereupon it became deep red. The THF was removed in vacuo, and the resulting red oil was dissolved in hexanes (30 ml) and filtered through a column of Celite (2 cm x 2 cm). The volume of this filtrate was reduced to 4 ml, and it was cooled to -30°C overnight to induce the deposition of (I) as a dark red powder (64 mg, 60% yield). X-ray quality crystals were grown from a concentrated hexanes solution at -30°C over the course of several weeks. IR (Nujol): 1635 cm^-1 (νNO). ¹H NMR (200 MHz, C₆D₆): δ 6.81 (t, 2H, C—H_m), 7.02 (dd, 2H, C—H_o), 5.19 (s, 5H, C₅H₅), 2.48 (d, 1H, CH₂SiMe₃), 1.97 (d, 1H, CH₂SiMe₃), 0.17 (s, 9H, SiCH₃). ¹³C NMR (200 MHz, C₆D₆): δ 118.6 (C—F), 116.1 (C—H_o), 115.6 (C—H_m), 104.7 (C₅H₅), 49.3 (CH₂Si), 1.93 (SiCH₃).

Data were collected in 0.50° oscillations with 60.0 s exposures. A sweep of data was carried out using ϕ oscillations from 0.0 to 190.0° at χ = -90° and a second sweep was performed using ω oscillations between -23.0 and 18.0° at χ = -90.0°. The crystal-to-detector distance was 39.25 mm. The detector swing angle was -10.43°.

Computing details top

Data collection: D*TREK (Molecular Structure Corporation, 1996-1998); cell refinement: D*TREK; data reduction: D*TREK; program(s) used to solve structure: SIR97 (Altomare et al., 1999); program(s) used to refine structure: TEXSAN (Molecular Structure Corporation, 1992-1997); software used to prepare material for publication: TEXSAN.

Figures top

Fig. 1. The molecular structure of (I) showing 50% probablilty ellipsoids.

(I) top

Crystal data top

[Mo(C₅H₅)(C₆H₄FO)(C₄H₁₁Si)(NO)]	Z = 2
M_r = 389.35	F(000) = 396.00
Triclinic, P1	D_x = 1.517 Mg m⁻³
a = 7.0052 (7) Å	Mo Kα radiation, λ = 0.7107 Å
b = 9.0510 (9) Å	Cell parameters from 4985 reflections
c = 14.021 (2) Å	θ = 3.1–27.9°
α = 103.510 (5)°	µ = 0.85 mm⁻¹
β = 98.776 (5)°	T = 180 K
γ = 91.830 (4)°	Irregular, red
V = 852.2 (1) Å³	0.25 × 0.20 × 0.06 mm

Data collection top

Rigaku/ADSC CCD diffractometer	3422 independent reflections
Radiation source: sealed tube	2674 reflections with I > 3σ(I)
Graphite monochromator	R_int = 0.043
Detector resolution: 11.76 pixels mm^-1	θ_max = 27.9°, θ_min = 3.1°
ϕ and ω scans	h = −7→8
Absorption correction: multi-scan (DTREK* MSC, 1996-1998) ?	k = −11→10
T_min = 0.73, T_max = 0.95	l = −18→15
7376 measured reflections

Refinement top

Refinement on F²	0 restraints
Least-squares matrix: full	0 constraints
R[F² > 2σ(F²)] = 0.029	H-atom parameters not refined
wR(F²) = 0.072	Weighting scheme based on measured s.u.'s w = 1/[σ²(F_o²)]
S = 0.86	(Δ/σ)_max = 0.001
3422 reflections	Δρ_max = 0.60 e Å⁻³
190 parameters	Δρ_min = −0.92 e Å⁻³

Crystal data top

[Mo(C₅H₅)(C₆H₄FO)(C₄H₁₁Si)(NO)]	γ = 91.830 (4)°
M_r = 389.35	V = 852.2 (1) Å³
Triclinic, P1	Z = 2
a = 7.0052 (7) Å	Mo Kα radiation
b = 9.0510 (9) Å	µ = 0.85 mm⁻¹
c = 14.021 (2) Å	T = 180 K
α = 103.510 (5)°	0.25 × 0.20 × 0.06 mm
β = 98.776 (5)°

Data collection top

Rigaku/ADSC CCD diffractometer	3422 independent reflections
Absorption correction: multi-scan (DTREK* MSC, 1996-1998) ?	2674 reflections with I > 3σ(I)
T_min = 0.73, T_max = 0.95	R_int = 0.043
7376 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.029	0 restraints
wR(F²) = 0.072	H-atom parameters not refined
S = 0.86	Δρ_max = 0.60 e Å⁻³
3422 reflections	Δρ_min = −0.92 e Å⁻³
190 parameters

Special details top

Experimental. Data were collected in 0.50° oscillations with 10.0 s exposures. A sweep of data was done using ϕ oscillations from 0.0 to 190.0° at χ = -90° and a second sweep was performed using ω oscillations between -23.0 and 18.0° at χ = 90.0°. The crystal-to-detector distance was 39.25 mm. The detector swing angle was -10.4°. The absorption correction is based on a three-dimensional analysis of symmetry-equivalent data and is performed along with batch scaling in a single step. The resulting transmission factors, therefore, include contributions from absorption, crystal decay, and detectable variations in beam intensity.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å²) top

	x	y	z	U_iso*/U_eq
Mo1	0.48307 (3)	0.39565 (3)	0.20474 (2)	0.01719 (7)
Si1	0.6767 (1)	0.1730 (1)	0.37501 (6)	0.0236 (2)
F1	−0.3157 (3)	0.0624 (2)	−0.1375 (1)	0.0439 (6)
O1	0.1359 (3)	0.3431 (3)	0.2918 (2)	0.0409 (7)
O2	0.3965 (3)	0.3195 (2)	0.0624 (1)	0.0225 (5)
N1	0.2755 (3)	0.3481 (3)	0.2515 (2)	0.0234 (7)
C1	0.4668 (5)	0.6536 (4)	0.2554 (3)	0.0342 (9)
C2	0.5770 (5)	0.6363 (4)	0.1777 (2)	0.0306 (9)
C3	0.7502 (4)	0.5781 (4)	0.2081 (2)	0.0286 (8)
C4	0.7522 (4)	0.5596 (3)	0.3057 (2)	0.0291 (8)
C5	0.5769 (5)	0.6094 (4)	0.3358 (2)	0.0315 (9)
C6	0.2174 (4)	0.2549 (3)	0.0134 (2)	0.0185 (7)
C7	0.2047 (4)	0.1199 (3)	−0.0601 (2)	0.0232 (8)
C8	0.0239 (5)	0.0553 (4)	−0.1118 (2)	0.0262 (8)
C9	−0.1377 (4)	0.1279 (4)	−0.0878 (2)	0.0265 (8)
C10	−0.1303 (4)	0.2598 (4)	−0.0169 (2)	0.0343 (9)
C11	0.0516 (5)	0.3247 (4)	0.0340 (2)	0.0303 (8)
C12	0.6576 (4)	0.2314 (3)	0.2553 (2)	0.0195 (7)
C13	0.8068 (6)	0.3251 (4)	0.4812 (2)	0.043 (1)
C14	0.8240 (5)	0.0030 (4)	0.3670 (3)	0.038 (1)
C15	0.4294 (5)	0.1242 (5)	0.3988 (3)	0.044 (1)
H1	0.3361	0.6896	0.2535	0.041*
H2	0.5382	0.6609	0.1134	0.037*
H3	0.8544	0.5541	0.1688	0.034*
H4	0.8562	0.5193	0.3452	0.035*
H5	0.5389	0.6131	0.4006	0.038*
H6	0.3225	0.0703	−0.0754	0.028*
H7	0.0125	−0.0391	−0.1639	0.031*
H8	−0.2489	0.3080	−0.0018	0.041*
H9	0.0608	0.4209	0.0847	0.036*
H10	0.6193	0.1367	0.2042	0.024*
H11	0.7902	0.2663	0.2527	0.024*
H12	0.8251	0.2870	0.5417	0.051*
H13	0.9334	0.3533	0.4664	0.051*
H14	0.7305	0.4146	0.4912	0.051*
H15	0.7553	−0.0832	0.3160	0.046*
H16	0.8442	−0.0239	0.4315	0.046*
H17	0.9496	0.0266	0.3494	0.046*
H18	0.3560	0.2158	0.4073	0.052*
H19	0.3618	0.0457	0.3425	0.052*
H20	0.4409	0.0868	0.4595	0.052*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Mo1	0.0119 (1)	0.0209 (1)	0.0174 (1)	−0.00086 (9)	0.00165 (8)	0.00270 (9)
Si1	0.0218 (4)	0.0256 (4)	0.0221 (4)	−0.0032 (3)	−0.0004 (3)	0.0066 (3)
F1	0.026 (1)	0.047 (1)	0.046 (1)	−0.0103 (9)	−0.0113 (9)	−0.001 (1)
O1	0.016 (1)	0.064 (2)	0.049 (1)	0.002 (1)	0.017 (1)	0.018 (1)
O2	0.018 (1)	0.028 (1)	0.018 (1)	−0.0024 (9)	−0.0008 (8)	0.0010 (8)
N1	0.016 (1)	0.031 (1)	0.023 (1)	0.001 (1)	0.004 (1)	0.005 (1)
C1	0.029 (2)	0.021 (2)	0.054 (2)	0.006 (1)	0.008 (2)	0.009 (2)
C2	0.031 (2)	0.026 (2)	0.036 (2)	−0.009 (1)	−0.001 (1)	0.015 (1)
C3	0.023 (2)	0.027 (2)	0.034 (2)	−0.011 (1)	0.009 (1)	0.001 (1)
C4	0.025 (2)	0.020 (2)	0.034 (2)	−0.006 (1)	−0.009 (1)	0.000 (1)
C5	0.046 (2)	0.020 (2)	0.024 (2)	−0.006 (1)	0.009 (1)	−0.005 (1)
C6	0.019 (1)	0.019 (1)	0.017 (1)	−0.001 (1)	−0.002 (1)	0.006 (1)
C7	0.024 (2)	0.025 (2)	0.020 (1)	0.002 (1)	0.007 (1)	0.003 (1)
C8	0.030 (2)	0.024 (2)	0.022 (2)	−0.002 (1)	0.003 (1)	0.003 (1)
C9	0.019 (2)	0.029 (2)	0.026 (2)	−0.005 (1)	−0.008 (1)	0.005 (1)
C10	0.020 (2)	0.041 (2)	0.034 (2)	0.010 (1)	−0.005 (1)	−0.001 (2)
C11	0.026 (2)	0.027 (2)	0.029 (2)	0.008 (1)	−0.004 (1)	−0.007 (1)
C12	0.014 (1)	0.019 (1)	0.023 (1)	−0.001 (1)	0.003 (1)	0.001 (1)
C13	0.058 (3)	0.044 (2)	0.021 (2)	−0.008 (2)	−0.002 (2)	0.004 (2)
C14	0.036 (2)	0.040 (2)	0.041 (2)	0.004 (2)	0.001 (2)	0.017 (2)
C15	0.033 (2)	0.063 (3)	0.043 (2)	−0.002 (2)	0.008 (2)	0.030 (2)

Geometric parameters (Å, º) top

Mo1—O2	1.945 (2)	C4—H4	0.98
Mo1—N1	1.764 (2)	C5—H5	0.98
Mo1—C1	2.288 (3)	C6—C7	1.394 (4)
Mo1—C2	2.386 (3)	C6—C11	1.377 (4)
Mo1—C3	2.443 (3)	C7—C8	1.395 (4)
Mo1—C4	2.405 (3)	C7—H6	0.98
Mo1—C5	2.333 (3)	C8—C9	1.373 (4)
Mo1—C12	2.133 (3)	C8—H7	0.98
Si1—C12	1.862 (3)	C9—C10	1.358 (4)
Si1—C13	1.869 (3)	C10—C11	1.399 (4)
Si1—C14	1.871 (4)	C10—H8	0.98
Si1—C15	1.872 (4)	C11—H9	0.98
F1—C9	1.373 (3)	C12—H10	0.98
O1—N1	1.207 (3)	C12—H11	0.98
O2—C6	1.375 (3)	C13—H12	0.98
C1—C2	1.412 (4)	C13—H13	0.98
C1—C5	1.411 (5)	C13—H14	0.98
C1—H1	0.98	C14—H15	0.98
C2—C3	1.385 (5)	C14—H16	0.98
C2—H2	0.98	C14—H17	0.98
C3—C4	1.414 (4)	C15—H18	0.98
C3—H3	0.98	C15—H19	0.98
C4—C5	1.412 (4)	C15—H20	0.98

Mo1···C1	2.288 (3)	O2···C1	3.519 (4)
Mo1···C5	2.333 (3)	N1···C5	3.011 (4)
Mo1···C2	2.386 (3)	N1···C1	3.019 (4)
Mo1···C4	2.405 (3)	C2···C7^iv	3.490 (4)
Mo1···C3	2.443 (3)	C2···C6^iv	3.542 (4)
F1···C2ⁱ	3.439 (4)	C3···C12	3.417 (4)
F1···C12ⁱⁱ	3.445 (3)	C4···C12	2.918 (4)
F1···C1ⁱ	3.476 (4)	C4···C13	3.594 (5)
F1···C7ⁱⁱ	3.544 (4)	C5···C12	3.437 (4)
O1···C4ⁱⁱⁱ	3.379 (4)	C7···C9ⁱⁱ	3.457 (4)
O1···C12ⁱⁱⁱ	3.395 (3)	C8···C8ⁱⁱ	3.564 (6)
O2···C2	3.068 (4)	C8···C9ⁱⁱ	3.576 (4)
O2···C3	3.412 (3)	C11···C11ⁱ	3.585 (7)
O2···C2^iv	3.513 (4)

O2—Mo1—N1	100.84 (9)	Mo1—C4—C3	74.5 (2)
O2—Mo1—C1	112.2 (1)	Mo1—C4—C5	69.9 (2)
O2—Mo1—C2	89.6 (1)	Mo1—C4—H4	121.1
O2—Mo1—C3	101.46 (9)	C3—C4—C5	107.7 (3)
O2—Mo1—C4	134.8 (1)	C3—C4—H4	126.2
O2—Mo1—C5	146.4 (1)	C5—C4—H4	126.1
O2—Mo1—C12	107.86 (9)	Mo1—C5—C1	70.5 (2)
N1—Mo1—C1	95.5 (1)	Mo1—C5—C4	75.5 (2)
N1—Mo1—C2	127.4 (1)	Mo1—C5—H5	119.8
N1—Mo1—C3	149.7 (1)	C1—C5—C4	107.4 (3)
N1—Mo1—C4	123.1 (1)	C1—C5—H5	126.2
N1—Mo1—C5	93.6 (1)	C4—C5—H5	126.4
N1—Mo1—C12	96.0 (1)	O2—C6—C7	119.4 (2)
C1—Mo1—C2	35.1 (1)	O2—C6—C11	120.7 (2)
C1—Mo1—C3	57.0 (1)	C7—C6—C11	119.8 (3)
C1—Mo1—C4	57.9 (1)	C6—C7—C8	119.8 (3)
C1—Mo1—C5	35.5 (1)	C6—C7—H6	120.1
C1—Mo1—C12	135.2 (1)	C8—C7—H6	120.1
C2—Mo1—C3	33.3 (1)	C7—C8—C9	118.4 (3)
C2—Mo1—C4	56.7 (1)	C7—C8—H7	120.8
C2—Mo1—C5	58.0 (1)	C9—C8—H7	120.8
C2—Mo1—C12	129.7 (1)	F1—C9—C8	118.2 (3)
C3—Mo1—C4	33.9 (1)	F1—C9—C10	118.5 (3)
C3—Mo1—C5	57.0 (1)	C8—C9—C10	123.3 (3)
C3—Mo1—C12	96.4 (1)	C9—C10—C11	118.1 (3)
C4—Mo1—C5	34.6 (1)	C9—C10—H8	120.9
C4—Mo1—C12	79.8 (1)	C11—C10—H8	121.0
C5—Mo1—C12	100.6 (1)	C6—C11—C10	120.6 (3)
C12—Si1—C13	111.7 (1)	C6—C11—H9	119.8
C12—Si1—C14	108.7 (1)	C10—C11—H9	119.6
C12—Si1—C15	109.9 (1)	Mo1—C12—Si1	129.2 (1)
C13—Si1—C14	106.5 (2)	Mo1—C12—H10	104.3
C13—Si1—C15	110.2 (2)	Mo1—C12—H11	104.2
C14—Si1—C15	109.8 (2)	Si1—C12—H10	104.5
Mo1—O2—C6	128.5 (2)	Si1—C12—H11	104.4
Mo1—N1—O1	168.2 (2)	H10—C12—H11	109.5
Mo1—C1—C2	76.2 (2)	Si1—C13—H12	109.5
Mo1—C1—C5	73.9 (2)	Si1—C13—H13	109.4
Mo1—C1—H1	115.8	Si1—C13—H14	109.5
C2—C1—C5	108.2 (3)	H12—C13—H13	109.4
C2—C1—H1	125.8	H12—C13—H14	109.5
C5—C1—H1	126.1	H13—C13—H14	109.5
Mo1—C2—C1	68.7 (2)	Si1—C14—H15	109.5
Mo1—C2—C3	75.6 (2)	Si1—C14—H16	109.5
Mo1—C2—H2	121.3	Si1—C14—H17	109.5
C1—C2—C3	108.0 (3)	H15—C14—H16	109.4
C1—C2—H2	126.1	H15—C14—H17	109.4
C3—C2—H2	125.9	H16—C14—H17	109.4
Mo1—C3—C2	71.1 (2)	Si1—C15—H18	109.3
Mo1—C3—C4	71.6 (2)	Si1—C15—H19	109.6
Mo1—C3—H3	123.5	Si1—C15—H20	109.5
C2—C3—C4	108.7 (3)	H18—C15—H19	109.5
C2—C3—H3	125.7	H18—C15—H20	109.3
C4—C3—H3	125.6	H19—C15—H20	109.7

Mo1—O2—C6—C7	−132.2 (2)	C1—Mo1—C3—C2	−37.9 (2)
Mo1—O2—C6—C11	49.9 (4)	C1—Mo1—C3—C4	80.2 (2)
Mo1—C1—C2—C3	−66.0 (2)	C1—Mo1—C4—C3	−77.4 (2)
Mo1—C1—C5—C4	67.1 (2)	C1—Mo1—C4—C5	38.5 (2)
Mo1—C2—C1—C5	67.7 (2)	C1—Mo1—C5—C4	−114.8 (3)
Mo1—C2—C3—C4	−62.0 (2)	C1—C2—Mo1—C3	−116.3 (3)
Mo1—C3—C2—C1	61.4 (2)	C1—C2—Mo1—C4	−80.2 (2)
Mo1—C3—C4—C5	−62.4 (2)	C1—C2—Mo1—C5	−38.8 (2)
Mo1—C4—C3—C2	61.7 (2)	C1—C2—Mo1—C12	−115.0 (2)
Mo1—C4—C5—C1	−63.7 (2)	C1—C2—C3—C4	−0.6 (3)
Mo1—C5—C1—C2	−69.2 (2)	C1—C5—Mo1—C2	38.3 (2)
Mo1—C5—C4—C3	65.5 (2)	C1—C5—Mo1—C3	78.1 (2)
Mo1—C12—Si1—C13	−71.7 (2)	C1—C5—Mo1—C4	114.8 (3)
Mo1—C12—Si1—C14	171.2 (2)	C1—C5—Mo1—C12	168.8 (2)
Mo1—C12—Si1—C15	50.9 (2)	C1—C5—C4—C3	1.8 (3)
Si1—C12—Mo1—O2	−143.6 (2)	C2—Mo1—O2—C6	−124.6 (2)
Si1—C12—Mo1—N1	−40.2 (2)	C2—Mo1—C1—C5	−113.9 (3)
Si1—C12—Mo1—C1	63.8 (2)	C2—Mo1—C3—C4	118.1 (3)
Si1—C12—Mo1—C2	111.5 (2)	C2—Mo1—C4—C3	−35.4 (2)
Si1—C12—Mo1—C3	112.2 (2)	C2—Mo1—C4—C5	80.5 (2)
Si1—C12—Mo1—C4	82.5 (2)	C2—Mo1—C5—C4	−76.5 (2)
Si1—C12—Mo1—C5	54.6 (2)	C2—C1—Mo1—C3	35.9 (2)
F1—C9—C8—C7	−178.7 (3)	C2—C1—Mo1—C4	76.4 (2)
F1—C9—C10—C11	179.3 (3)	C2—C1—Mo1—C5	113.9 (3)
O1—N1—Mo1—O2	−125 (1)	C2—C1—Mo1—C12	98.2 (2)
O1—N1—Mo1—C1	−11 (1)	C2—C1—C5—C4	−2.1 (4)
O1—N1—Mo1—C2	−27 (1)	C2—C3—Mo1—C4	−118.1 (3)
O1—N1—Mo1—C3	12 (1)	C2—C3—Mo1—C5	−80.6 (2)
O1—N1—Mo1—C4	44 (1)	C2—C3—Mo1—C12	−179.0 (2)
O1—N1—Mo1—C5	24 (1)	C2—C3—C4—C5	−0.7 (3)
O1—N1—Mo1—C12	125 (1)	C3—Mo1—O2—C6	−156.0 (2)
O2—Mo1—C1—C2	−53.6 (2)	C3—Mo1—C1—C5	−78.0 (2)
O2—Mo1—C1—C5	−167.4 (2)	C3—Mo1—C4—C5	115.9 (3)
O2—Mo1—C2—C1	131.8 (2)	C3—Mo1—C5—C4	−36.7 (2)
O2—Mo1—C2—C3	−111.9 (2)	C3—C2—Mo1—C4	36.1 (2)
O2—Mo1—C3—C2	71.2 (2)	C3—C2—Mo1—C5	77.5 (2)
O2—Mo1—C3—C4	−170.6 (2)	C3—C2—Mo1—C12	1.3 (2)
O2—Mo1—C4—C3	13.0 (3)	C3—C2—C1—C5	1.7 (4)
O2—Mo1—C4—C5	128.9 (2)	C3—C4—Mo1—C5	−115.9 (3)
O2—Mo1—C5—C1	21.3 (3)	C3—C4—Mo1—C12	118.1 (2)
O2—Mo1—C5—C4	−93.5 (3)	C4—Mo1—O2—C6	−163.3 (2)
O2—C6—C7—C8	−178.6 (3)	C4—Mo1—C1—C5	−37.5 (2)
O2—C6—C11—C10	179.1 (3)	C4—C3—Mo1—C5	37.6 (2)
N1—Mo1—O2—C6	3.4 (2)	C4—C3—Mo1—C12	−60.9 (2)
N1—Mo1—C1—C2	−157.6 (2)	C4—C5—Mo1—C12	54.0 (2)
N1—Mo1—C1—C5	88.5 (2)	C5—Mo1—O2—C6	−110.3 (3)
N1—Mo1—C2—C1	28.5 (2)	C5—C1—Mo1—C12	−15.7 (3)
N1—Mo1—C2—C3	144.8 (2)	C5—C4—Mo1—C12	−126.1 (2)
N1—Mo1—C3—C2	−65.5 (3)	C6—O2—Mo1—C12	103.4 (2)
N1—Mo1—C3—C4	52.6 (3)	C6—C7—C8—C9	−0.2 (5)
N1—Mo1—C4—C3	−151.4 (2)	C6—C11—C10—C9	−1.0 (5)
N1—Mo1—C4—C5	−35.5 (2)	C7—C6—C11—C10	1.3 (5)
N1—Mo1—C5—C1	−94.4 (2)	C7—C8—C9—C10	0.5 (5)
N1—Mo1—C5—C4	150.8 (2)	C8—C7—C6—C11	−0.7 (5)
C1—Mo1—O2—C6	−97.1 (2)	C8—C9—C10—C11	0.1 (6)
C1—Mo1—C2—C3	116.3 (3)

Symmetry codes: (i) −x, −y+1, −z; (ii) −x, −y, −z; (iii) x−1, y, z; (iv) −x+1, −y+1, −z.

Experimental details

Crystal data
Chemical formula	[Mo(C₅H₅)(C₆H₄FO)(C₄H₁₁Si)(NO)]
M_r	389.35
Crystal system, space group	Triclinic, P1
Temperature (K)	180
a, b, c (Å)	7.0052 (7), 9.0510 (9), 14.021 (2)
α, β, γ (°)	103.510 (5), 98.776 (5), 91.830 (4)
V (Å³)	852.2 (1)
Z	2
Radiation type	Mo Kα
µ (mm⁻¹)	0.85
Crystal size (mm)	0.25 × 0.20 × 0.06

Data collection
Diffractometer	Rigaku/ADSC CCD diffractometer
Absorption correction	Multi-scan (DTREK* MSC, 1996-1998)
T_min, T_max	0.73, 0.95
No. of measured, independent and observed [I > 3σ(I)] reflections	7376, 3422, 2674
R_int	0.043
(sin θ/λ)_max (Å⁻¹)	0.658

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.029, 0.072, 0.86
No. of reflections	3422
No. of parameters	190
H-atom treatment	H-atom parameters not refined
Δρ_max, Δρ_min (e Å⁻³)	0.60, −0.92

Computer programs: D*TREK (Molecular Structure Corporation, 1996-1998), D*TREK, SIR97 (Altomare et al., 1999), TEXSAN (Molecular Structure Corporation, 1992-1997), TEXSAN.

Selected geometric parameters (Å, º) top

Mo1—O2	1.945 (2)	Mo1—C3	2.443 (3)
Mo1—N1	1.764 (2)	Mo1—C4	2.405 (3)
Mo1—C1	2.288 (3)	Mo1—C5	2.333 (3)
Mo1—C2	2.386 (3)	Mo1—C12	2.133 (3)

O2—Mo1—N1	100.84 (9)	Mo1—O2—C6	128.5 (2)
O2—Mo1—C12	107.86 (9)	Mo1—N1—O1	168.2 (2)
N1—Mo1—C12	96.0 (1)	Mo1—C12—Si1	129.2 (1)

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(η5-Cyclo­penta­dienyl)(p-fluoro­phenoxo)(nitro­syl)(tri­methyl­silyl­methyl)­molybdenum(II)

Supporting information

(η⁵-Cyclopentadienyl)(p-fluorophenoxo)(nitrosyl)(trimethylsilylmethyl)molybdenum(II)