Bis(η6-naphthalene)­molybdenum(0)

Minyaev, M.E.; Ellis, J.E.; Wolf, W.J.

doi:10.1107/S1600536812002504

metal-organic compounds

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ISSN: 2056-9890

Volume 68| Part 2| February 2012| Page m220

doi:10.1107/S1600536812002504

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Bis(η⁶-naphthalene)molybdenum(0)

Mikhail E. Minyaev,^a ^* John E. Ellis ^b and William J. Wolf ^b

^aInstitute of Organoelement Compounds, 28 Vavilova Str., 117813 Moscow, Russian Federation, and ^bDepartment of Chemistry, University of Minnesota, Minneapolis, 207 Pleasant Str. SE, MN 55455, USA
^*Correspondence e-mail: mminyaev@mail.ru

(Received 22 December 2011; accepted 19 January 2012; online 31 January 2012)

The title compound, [Mo(C₁₀H₈)₂], was prepared from the naphthalene radical anion and MoCl₄(thf)₂ (thf is tetrahydrofuran). In the crystal, the molecule is located on an inversion center. The Mo atom is equally disordered over two positions; the range of Mo—C distances is 2.2244 (19)–2.3400 (17) Å for both components of the disorder.

Related literature

For background to transition metal–arene complexes, see: Seyferth (2002a ,b ). For the structures of the isotypic Cr and V complexes, see: Elschenbroich et al. (1982 ); Pomije et al. (1997 ). For the structures of homoleptic naphthalenate ate-complexes, see: Jang & Ellis (1994 ); Brennessel et al. (2002 , 2006 ). For the preparation of the title compound, see: Kündig & Timms (1977 ); Thi et al. (1992 ); Pomije et al. (1997).

Experimental

Crystal data

[Mo(C₁₀H₈)₂]
M_r = 352.27
Monoclinic, P 2₁ /n
a = 8.4452 (10) Å
b = 8.0716 (10) Å
c = 10.9890 (13) Å
β = 109.186 (2)°
V = 707.47 (15) Å³
Z = 2
Mo Kα radiation
μ = 0.92 mm⁻¹
T = 173 K
0.60 × 0.60 × 0.30 mm

Data collection

Bruker SMART Platform CCD diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2003 ) T_min = 0.610, T_max = 0.771
8208 measured reflections
1674 independent reflections
1420 reflections with I > 2σ(I)
R_int = 0.031

Refinement

R[F² > 2σ(F²)] = 0.028
wR(F²) = 0.069
S = 1.03
1674 reflections
132 parameters
All H-atom parameters refined
Δρ_max = 0.27 e Å⁻³
Δρ_min = −0.28 e Å⁻³

Data collection: SMART (Bruker, 2003); cell refinement: SAINT (Bruker, 2003); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXTL.

Supporting information

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536812002504/tk5041sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536812002504/tk5041Isup2.hkl

Supporting information file. DOI: 10.1107/S1600536812002504/tk5041Isup3.mol

checkCIF report

Comment top

Studies of classical arene complexes of transition elements have had significant impact on understanding metal – organic ligand bonding (Seyferth, 2002a,b). However, only a few molecular structures of d-metal neutral homoleptic naphthalene species, i.e. Cr(η⁶-C₁₀H₈)₂ (Elschenbroich et al., 1982), V(η⁶-C₁₀H₈)₂ (Pomije et al., 1997) and homoleptic naphthalene ate-complexes [Zr(η⁴-C₁₀H₈)₃]^2- (Jang et al., 1994), [Ta(η⁴-C₁₀H₈)₃]^- (Brennessel et al., 2002) and [Co(η⁴-C₁₀H₈)₂]^- (Brennessel et al., 2006), have been established.

Previous examples of neutral homoleptic naphthalene complexes of transition metals were obtained by metal-atom-ligand-vapor co-condensation synthesis (Kündig et al., 1977). The title compound, Mo(η⁶-C₁₀H₈)₂, was later obtained by reduction of MoCl₅ or MoCl₄(thf)₂ with Mg, followed by evaporation of Mo atoms along with free naphthalene under vacuum (Thi et al., 1992), or by reduction of MoCl₄(thf)₂ or MoCl₃(thf)₃ with lithium naphthalenide (Pomije et al., 1997).

We prepared Mo(C₁₀H₈)₂ from LiC₁₀H₈ and MoCl₄(thf)₂ under argon in THF media in 13% yield. The ¹H NMR spectrum is identical with previously described by Pomije et al. (1997). The Mo(C₁₀H₈)₂ crystal structure is isomorphous with previously published structures of Cr(C₁₀H₈)₂ (Elschenbroich et al., 1982) and V(C₁₀H₈)₂ (Pomije et al., 1997). The molecule is located on the inversion center, one half of the molecule is unique. The molybdenum atom is disordered equally between two positions with occupancy of 50%. The C–C distances are similar to those found in Cr(C₁₀H₈)₂ and V(C₁₀H₈)₂. The Mo–centroid(C₆) distances are 1.782 Å (C1—C2—C3—C4—C9—C10) and 1.770 Å (C5—C6—C7—C8—C10—C9) and centroid(C₆)–Mo–centroid(C₆) angle is 178°. The naphthalene ligand is slightly bent along the C9—C10 bond towards molybdenum atom, the angle between flat rings in the naphthalene ligand is 177°.

Related literature top

For background to transition metal–arene complexes, see: Seyferth (2002a,b). For related d-metal neutral homoleptic naphthalene structures, see: Elschenbroich et al. (1982); Pomije et al. (1997). For the structures of homoleptic naphthalene ate-complexes, see: Jang & Ellis (1994); Brennessel et al. (2002, 2006). For the preparation of the title compound, see: Kündig & Timms (1977); Thi et al. (1992); Pomije et al. (1997). For the structures of the isotypic Cr and V complexes, see: Elschenbroich et al. (1982); Pomije et al. (1997).

Experimental top

All synthetic manipulations were carried out in atmosphere of purified argon or under vacuum, using Schlenk type glassware and dry box techniques. Freshly cut lithium wire (0.34 g, 49 mmol), sublimed naphthalene (9.15 g, 71.4 mmol) and THF (200 ml) were added to a 1 L round-bottomed flask equipped with a glass covered stirbar. The mixture was stirred for 17 h at ambient temperature, then the resulting deep green solution was cooled to -60°C. A cold (-60°C) suspension of MoCl₄(thf)₂ (4.5 g, 11.8 mmol) and C₁₀H₈ (6.10 g, 47.6 mmol) in THF (100 ml) was added dropwise to the cold solution of lithium naphthalenide via large cannula. The reaction mixture was allowed to warm to ambient temperature over 15 h. It was filtered to provide a dark red solution, then THF was removed under vacuum. The resulting solid was stirred in toluene (200 ml), the mixture was filtered, and all toluene was removed from the solution under vacuum. The remaining solid was transferred to a sublimator, and an excess of naphthalene was removed by sublimation under vacuum at 30°C over three days. The remaining purple brown solid was taken up in toluene (100 ml) and the solution was filtered. All but 5 ml of toluene was removed under vacuum, pentane (100 ml) was added. The resulting mixture was cooled to -78°C and stirred. The precipitate was filtered off to give Mo(C₁₀H₈)₂ (0.539 g, 1.53 mmol, 13.0%) as a dark purple microcrystalline solid. ¹H NMR (300 MHz, C₆D₆, 25°C): δ (p.p.m.) = 4.67 (m, 2H). 5.02 (m, 2H), 6.56 (m, 2H), 6.78 (m, 2H) p.p.m..

X-ray quality single crystals were grown at 0°C over a 2 week period by slow diffusion of pentane (100 ml) into a nearly saturated solution of Mo(C₁₀H₈)₂ (100 mg) in toluene (c.a. 20 ml).

Computing details top

Data collection: SMART (Bruker, 2003); cell refinement: SAINT (Bruker, 2003); data reduction: SAINT (Bruker, 2003); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXTL (Sheldrick, 2008).

Figures top

Fig. 1. Molecular structure of Mo(C₁₀H₈)₂ (50% atomic displacement parameters). The asymmetric unit consists of one half of the molecule. The occupancies of Mo1 and Mo1ⁱ sites are 50%. Symmetry code: (i) -x + 1, -y, -z + 2.

Bis(η⁶-naphthalene)molybdenum(0) top

Crystal data top

[Mo(C₁₀H₈)₂]	F(000) = 356
M_r = 352.27	D_x = 1.654 Mg m⁻³
Monoclinic, P2₁/n	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2yn	Cell parameters from 2191 reflections
a = 8.4452 (10) Å	θ = 2.7–28.3°
b = 8.0716 (10) Å	µ = 0.92 mm⁻¹
c = 10.9890 (13) Å	T = 173 K
β = 109.186 (2)°	Block, dark-red
V = 707.47 (15) Å³	0.60 × 0.60 × 0.30 mm
Z = 2

Data collection top

Bruker SMART Platform CCD diffractometer	1674 independent reflections
Radiation source: normal-focus sealed tube	1420 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.031
area detector, ω and ϕ scans	θ_max = 27.9°, θ_min = 2.7°
Absorption correction: multi-scan (SADABS; Bruker, 2003)	h = −10→11
T_min = 0.610, T_max = 0.771	k = −10→10
8208 measured reflections	l = −14→14

Refinement top

Refinement on F²	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F² > 2σ(F²)] = 0.028	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.069	All H-atom parameters refined
S = 1.03	w = 1/[σ²(F_o²) + (0.0357P)² + 0.251P] where P = (F_o² + 2F_c²)/3
1674 reflections	(Δ/σ)_max = 0.001
132 parameters	Δρ_max = 0.27 e Å⁻³
0 restraints	Δρ_min = −0.28 e Å⁻³

Crystal data top

[Mo(C₁₀H₈)₂]	V = 707.47 (15) Å³
M_r = 352.27	Z = 2
Monoclinic, P2₁/n	Mo Kα radiation
a = 8.4452 (10) Å	µ = 0.92 mm⁻¹
b = 8.0716 (10) Å	T = 173 K
c = 10.9890 (13) Å	0.60 × 0.60 × 0.30 mm
β = 109.186 (2)°

Data collection top

Bruker SMART Platform CCD diffractometer	1674 independent reflections
Absorption correction: multi-scan (SADABS; Bruker, 2003)	1420 reflections with I > 2σ(I)
T_min = 0.610, T_max = 0.771	R_int = 0.031
8208 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.028	0 restraints
wR(F²) = 0.069	All H-atom parameters refined
S = 1.03	Δρ_max = 0.27 e Å⁻³
1674 reflections	Δρ_min = −0.28 e Å⁻³
132 parameters

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.

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

	x	y	z	U_iso*/U_eq	Occ. (<1)
Mo1	0.63424 (3)	0.01329 (3)	0.97463 (3)	0.02253 (11)	0.50
C1	0.4807 (3)	0.0582 (3)	0.76370 (18)	0.0382 (4)
C2	0.6382 (3)	0.1252 (3)	0.7895 (2)	0.0481 (6)
C3	0.7005 (3)	0.2429 (3)	0.8901 (2)	0.0452 (5)
C4	0.6048 (2)	0.2901 (2)	0.96470 (19)	0.0358 (4)
C9	0.4393 (2)	0.22530 (19)	0.93978 (16)	0.0261 (4)
C5	0.3393 (2)	0.2642 (2)	1.01832 (17)	0.0318 (4)
C6	0.1831 (3)	0.1938 (2)	0.99537 (19)	0.0358 (4)
C7	0.1202 (2)	0.0780 (3)	0.89365 (19)	0.0372 (4)
C8	0.2145 (2)	0.0343 (2)	0.81728 (17)	0.0330 (4)
C10	0.3753 (2)	0.1064 (2)	0.83615 (15)	0.0277 (4)
H1	0.442 (3)	−0.021 (2)	0.702 (2)	0.040 (6)*
H2	0.707 (3)	0.091 (3)	0.744 (2)	0.058 (7)*
H3	0.806 (3)	0.289 (3)	0.910 (2)	0.058 (7)*
H4	0.641 (3)	0.363 (3)	1.032 (2)	0.037 (6)*
H5	0.380 (2)	0.337 (2)	1.086 (2)	0.034 (5)*
H6	0.118 (3)	0.218 (3)	1.048 (2)	0.047 (6)*
H7	0.021 (3)	0.024 (3)	0.881 (2)	0.049 (7)*
H8	0.179 (3)	−0.044 (3)	0.758 (2)	0.034 (5)*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Mo1	0.02548 (16)	0.02166 (16)	0.01930 (16)	0.00090 (11)	0.00579 (11)	0.00237 (10)
C1	0.0496 (12)	0.0428 (11)	0.0217 (9)	0.0128 (9)	0.0111 (8)	0.0065 (8)
C2	0.0527 (13)	0.0604 (14)	0.0398 (12)	0.0210 (11)	0.0268 (11)	0.0232 (10)
C3	0.0342 (11)	0.0442 (12)	0.0579 (14)	0.0024 (9)	0.0160 (10)	0.0263 (10)
C4	0.0372 (11)	0.0238 (9)	0.0396 (11)	−0.0031 (7)	0.0036 (9)	0.0086 (8)
C9	0.0314 (9)	0.0194 (8)	0.0246 (8)	0.0017 (6)	0.0054 (7)	0.0048 (6)
C5	0.0420 (11)	0.0229 (8)	0.0276 (9)	0.0049 (7)	0.0078 (8)	−0.0004 (7)
C6	0.0368 (10)	0.0364 (10)	0.0359 (10)	0.0079 (8)	0.0143 (9)	0.0045 (8)
C7	0.0286 (10)	0.0366 (10)	0.0410 (11)	−0.0017 (8)	0.0043 (8)	0.0086 (8)
C8	0.0390 (10)	0.0259 (9)	0.0245 (9)	−0.0003 (7)	−0.0025 (8)	0.0005 (7)
C10	0.0350 (9)	0.0248 (8)	0.0194 (8)	0.0050 (7)	0.0038 (7)	0.0056 (6)

Geometric parameters (Å, º) top

Mo1—C1	2.2826 (19)	C4—C9	1.432 (3)
Mo1—C2	2.236 (2)	C9—C5	1.427 (3)
Mo1—C3	2.225 (2)	C5—C6	1.381 (3)
Mo1—C4	2.2466 (19)	C6—C7	1.419 (3)
Mo1—C9	2.3176 (16)	C7—C8	1.379 (3)
Mo1—C10	2.3400 (17)	C8—C10	1.429 (3)
Mo1—C5ⁱ	2.2495 (18)	C9—C10	1.451 (2)
Mo1—C6ⁱ	2.2244 (19)	C1—H1	0.91 (2)
Mo1—C7ⁱ	2.2284 (19)	C2—H2	0.93 (2)
Mo1—C8ⁱ	2.2557 (18)	C3—H3	0.92 (3)
Mo1—C9ⁱ	2.3158 (16)	C4—H4	0.91 (2)
Mo1—C10ⁱ	2.3182 (16)	C5—H5	0.92 (2)
C1—C10	1.429 (3)	C6—H6	0.94 (2)
C1—C2	1.377 (3)	C7—H7	0.91 (3)
C2—C3	1.421 (3)	C8—H8	0.89 (2)
C3—C4	1.380 (3)

C6ⁱ—Mo1—C3	115.50 (8)	C2—C1—Mo1	70.43 (12)
C6ⁱ—Mo1—C7ⁱ	37.18 (7)	C10—C1—Mo1	74.19 (10)
C3—Mo1—C7ⁱ	103.80 (8)	C1—C2—C3	120.6 (2)
C6ⁱ—Mo1—C2	102.80 (8)	C1—C2—Mo1	74.12 (12)
C3—Mo1—C2	37.15 (9)	C3—C2—Mo1	71.01 (12)
C7ⁱ—Mo1—C2	115.83 (8)	C4—C3—C2	120.5 (2)
C6ⁱ—Mo1—C4	144.57 (7)	C4—C3—Mo1	72.87 (11)
C3—Mo1—C4	35.95 (8)	C2—C3—Mo1	71.84 (12)
C7ⁱ—Mo1—C4	115.15 (7)	C3—C4—C9	120.73 (19)
C2—Mo1—C4	65.70 (8)	C3—C4—Mo1	71.18 (12)
C6ⁱ—Mo1—C5ⁱ	35.95 (7)	C9—C4—Mo1	74.44 (10)
C3—Mo1—C5ⁱ	143.88 (8)	C5—C9—C4	122.59 (17)
C7ⁱ—Mo1—C5ⁱ	65.64 (7)	C5—C9—C10	118.58 (16)
C2—Mo1—C5ⁱ	113.74 (8)	C4—C9—C10	118.68 (17)
C4—Mo1—C5ⁱ	179.14 (7)	C5—C9—Mo1ⁱ	69.28 (9)
C6ⁱ—Mo1—C8ⁱ	65.65 (7)	C4—C9—Mo1ⁱ	126.95 (11)
C3—Mo1—C8ⁱ	115.38 (8)	C10—C9—Mo1ⁱ	71.85 (9)
C7ⁱ—Mo1—C8ⁱ	35.82 (7)	C5—C9—Mo1	126.30 (11)
C2—Mo1—C8ⁱ	144.91 (9)	C4—C9—Mo1	69.04 (10)
C4—Mo1—C8ⁱ	103.61 (7)	C10—C9—Mo1	72.69 (9)
C5ⁱ—Mo1—C8ⁱ	77.22 (7)	Mo1ⁱ—C9—Mo1	65.77 (4)
C6ⁱ—Mo1—C1	113.87 (7)	C6—C5—C9	121.25 (17)
C3—Mo1—C1	65.22 (9)	C6—C5—Mo1ⁱ	71.04 (11)
C7ⁱ—Mo1—C1	144.00 (8)	C9—C5—Mo1ⁱ	74.33 (9)
C2—Mo1—C1	35.45 (8)	C5—C6—C7	120.16 (19)
C4—Mo1—C1	77.05 (7)	C5—C6—Mo1ⁱ	73.01 (11)
C5ⁱ—Mo1—C1	102.12 (7)	C7—C6—Mo1ⁱ	71.56 (11)
C8ⁱ—Mo1—C1	179.33 (7)	C8—C7—C6	120.40 (19)
C6ⁱ—Mo1—C9ⁱ	65.18 (7)	C8—C7—Mo1ⁱ	73.17 (11)
C3—Mo1—C9ⁱ	179.04 (7)	C6—C7—Mo1ⁱ	71.26 (11)
C7ⁱ—Mo1—C9ⁱ	77.15 (7)	C7—C8—C10	121.25 (17)
C2—Mo1—C9ⁱ	142.34 (8)	C7—C8—Mo1ⁱ	71.01 (11)
C4—Mo1—C9ⁱ	143.76 (7)	C10—C8—Mo1ⁱ	74.20 (10)
C5ⁱ—Mo1—C9ⁱ	36.39 (6)	C8—C10—C1	122.96 (17)
C8ⁱ—Mo1—C9ⁱ	65.46 (6)	C8—C10—C9	118.33 (16)
C1—Mo1—C9ⁱ	113.94 (7)	C1—C10—C9	118.56 (17)
C6ⁱ—Mo1—C9	178.65 (7)	C8—C10—Mo1ⁱ	69.43 (10)
C3—Mo1—C9	65.07 (7)	C1—C10—Mo1ⁱ	126.69 (12)
C7ⁱ—Mo1—C9	144.14 (7)	C9—C10—Mo1ⁱ	71.66 (9)
C2—Mo1—C9	76.91 (7)	C8—C10—Mo1	127.15 (11)
C4—Mo1—C9	36.52 (6)	C1—C10—Mo1	69.81 (10)
C5ⁱ—Mo1—C9	142.94 (7)	C9—C10—Mo1	71.02 (9)
C8ⁱ—Mo1—C9	115.35 (7)	Mo1ⁱ—C10—Mo1	65.37 (4)
C1—Mo1—C9	65.12 (7)	C2—C1—H1	120.8 (14)
C9ⁱ—Mo1—C9	114.23 (4)	C10—C1—H1	118.2 (14)
C6ⁱ—Mo1—C10ⁱ	77.33 (7)	Mo1—C1—H1	126.2 (13)
C3—Mo1—C10ⁱ	144.01 (8)	C1—C2—H2	120.5 (16)
C7ⁱ—Mo1—C10ⁱ	65.09 (7)	C3—C2—H2	118.9 (16)
C2—Mo1—C10ⁱ	178.65 (8)	Mo1—C2—H2	125.0 (15)
C4—Mo1—C10ⁱ	114.97 (7)	C4—C3—H3	117.5 (15)
C5ⁱ—Mo1—C10ⁱ	65.57 (6)	C2—C3—H3	122.1 (15)
C8ⁱ—Mo1—C10ⁱ	36.37 (7)	Mo1—C3—H3	126.5 (15)
C1—Mo1—C10ⁱ	143.26 (7)	C3—C4—H4	123.6 (13)
C9ⁱ—Mo1—C10ⁱ	36.49 (6)	C9—C4—H4	115.7 (13)
C9—Mo1—C10ⁱ	102.93 (6)	Mo1—C4—H4	126.8 (13)
C6ⁱ—Mo1—C10	142.39 (7)	C6—C5—H5	119.4 (12)
C3—Mo1—C10	76.73 (7)	C9—C5—H5	119.4 (12)
C7ⁱ—Mo1—C10	179.42 (7)	Mo1ⁱ—C5—H5	127.2 (12)
C2—Mo1—C10	64.45 (7)	C5—C6—H6	121.2 (14)
C4—Mo1—C10	65.41 (6)	C7—C6—H6	118.6 (14)
C5ⁱ—Mo1—C10	113.79 (6)	Mo1ⁱ—C6—H6	125.7 (14)
C8ⁱ—Mo1—C10	144.17 (7)	C8—C7—H7	118.3 (15)
C1—Mo1—C10	35.99 (6)	C6—C7—H7	121.1 (15)
C9ⁱ—Mo1—C10	102.32 (6)	Mo1ⁱ—C7—H7	123.6 (14)
C9—Mo1—C10	36.29 (6)	C7—C8—H8	120.6 (13)
C10ⁱ—Mo1—C10	114.63 (4)	C10—C8—H8	118.1 (13)
C2—C1—C10	121.0 (2)	Mo1ⁱ—C8—H8	124.5 (13)

C6ⁱ—Mo1—C1—C2	−78.24 (15)	C9ⁱ—Mo1—C9—C4	151.44 (12)
C3—Mo1—C1—C2	30.08 (13)	C10ⁱ—Mo1—C9—C4	114.69 (11)
C7ⁱ—Mo1—C1—C2	−49.1 (2)	C10—Mo1—C9—C4	−131.12 (15)
C4—Mo1—C1—C2	66.11 (14)	C3—Mo1—C9—C10	101.84 (12)
C5ⁱ—Mo1—C1—C2	−114.10 (14)	C7ⁱ—Mo1—C9—C10	−179.35 (11)
C9ⁱ—Mo1—C1—C2	−150.44 (13)	C2—Mo1—C9—C10	64.44 (11)
C9—Mo1—C1—C2	102.75 (15)	C4—Mo1—C9—C10	131.12 (15)
C10ⁱ—Mo1—C1—C2	−179.30 (12)	C5ⁱ—Mo1—C9—C10	−47.76 (15)
C10—Mo1—C1—C2	131.9 (2)	C8ⁱ—Mo1—C9—C10	−150.53 (10)
C6ⁱ—Mo1—C1—C10	149.85 (11)	C1—Mo1—C9—C10	28.93 (10)
C3—Mo1—C1—C10	−101.83 (13)	C9ⁱ—Mo1—C9—C10	−77.43 (9)
C7ⁱ—Mo1—C1—C10	179.02 (11)	C10ⁱ—Mo1—C9—C10	−114.18 (8)
C2—Mo1—C1—C10	−131.9 (2)	C3—Mo1—C9—Mo1ⁱ	179.28 (8)
C4—Mo1—C1—C10	−65.80 (12)	C7ⁱ—Mo1—C9—Mo1ⁱ	−101.91 (11)
C5ⁱ—Mo1—C1—C10	113.99 (12)	C2—Mo1—C9—Mo1ⁱ	141.87 (8)
C9ⁱ—Mo1—C1—C10	77.65 (12)	C4—Mo1—C9—Mo1ⁱ	−151.44 (12)
C9—Mo1—C1—C10	−29.17 (10)	C5ⁱ—Mo1—C9—Mo1ⁱ	29.67 (11)
C10ⁱ—Mo1—C1—C10	48.78 (19)	C8ⁱ—Mo1—C9—Mo1ⁱ	−73.10 (7)
C10—C1—C2—C3	0.7 (3)	C1—Mo1—C9—Mo1ⁱ	106.36 (7)
Mo1—C1—C2—C3	−55.86 (17)	C9ⁱ—Mo1—C9—Mo1ⁱ	0.0
C10—C1—C2—Mo1	56.59 (17)	C10ⁱ—Mo1—C9—Mo1ⁱ	−36.75 (6)
C6ⁱ—Mo1—C2—C1	113.35 (13)	C10—Mo1—C9—Mo1ⁱ	77.43 (9)
C3—Mo1—C2—C1	−131.1 (2)	C4—C9—C5—C6	−177.00 (16)
C7ⁱ—Mo1—C2—C1	150.43 (12)	C10—C9—C5—C6	−1.4 (2)
C4—Mo1—C2—C1	−102.13 (14)	Mo1ⁱ—C9—C5—C6	−55.60 (15)
C5ⁱ—Mo1—C2—C1	77.16 (14)	Mo1—C9—C5—C6	−90.3 (2)
C8ⁱ—Mo1—C2—C1	179.02 (12)	C4—C9—C5—Mo1ⁱ	−121.39 (15)
C9ⁱ—Mo1—C2—C1	47.56 (19)	C10—C9—C5—Mo1ⁱ	54.17 (13)
C9—Mo1—C2—C1	−65.29 (13)	Mo1—C9—C5—Mo1ⁱ	−34.68 (12)
C10—Mo1—C2—C1	−29.00 (12)	C9—C5—C6—C7	1.2 (3)
C6ⁱ—Mo1—C2—C3	−115.54 (13)	Mo1ⁱ—C5—C6—C7	−55.95 (16)
C7ⁱ—Mo1—C2—C3	−78.46 (14)	C9—C5—C6—Mo1ⁱ	57.15 (15)
C4—Mo1—C2—C3	28.97 (12)	C5—C6—C7—C8	0.3 (3)
C5ⁱ—Mo1—C2—C3	−151.74 (12)	Mo1ⁱ—C6—C7—C8	−56.39 (16)
C8ⁱ—Mo1—C2—C3	−49.88 (19)	C5—C6—C7—Mo1ⁱ	56.64 (16)
C1—Mo1—C2—C3	131.10 (19)	C6—C7—C8—C10	−1.4 (3)
C9ⁱ—Mo1—C2—C3	178.66 (11)	Mo1ⁱ—C7—C8—C10	−56.93 (15)
C9—Mo1—C2—C3	65.81 (13)	C6—C7—C8—Mo1ⁱ	55.48 (16)
C10—Mo1—C2—C3	102.10 (13)	C7—C8—C10—C1	176.59 (16)
C1—C2—C3—C4	0.9 (3)	Mo1ⁱ—C8—C10—C1	121.15 (16)
Mo1—C2—C3—C4	−56.46 (16)	C7—C8—C10—C9	1.2 (2)
C1—C2—C3—Mo1	57.35 (17)	Mo1ⁱ—C8—C10—C9	−54.27 (13)
C6ⁱ—Mo1—C3—C4	−151.64 (12)	C7—C8—C10—Mo1ⁱ	55.44 (16)
C7ⁱ—Mo1—C3—C4	−114.00 (13)	C7—C8—C10—Mo1	88.0 (2)
C2—Mo1—C3—C4	131.25 (19)	Mo1ⁱ—C8—C10—Mo1	32.57 (12)
C5ⁱ—Mo1—C3—C4	178.57 (12)	C2—C1—C10—C8	−176.75 (16)
C8ⁱ—Mo1—C3—C4	−77.86 (14)	Mo1—C1—C10—C8	−121.91 (16)
C1—Mo1—C3—C4	102.48 (14)	C2—C1—C10—C9	−1.3 (3)
C9—Mo1—C3—C4	29.72 (11)	Mo1—C1—C10—C9	53.51 (13)
C10ⁱ—Mo1—C3—C4	−47.57 (18)	C2—C1—C10—Mo1ⁱ	−89.0 (2)
C10—Mo1—C3—C4	66.25 (12)	Mo1—C1—C10—Mo1ⁱ	−34.14 (14)
C6ⁱ—Mo1—C3—C2	77.11 (14)	C2—C1—C10—Mo1	−54.85 (17)
C7ⁱ—Mo1—C3—C2	114.75 (13)	C5—C9—C10—C8	0.3 (2)
C4—Mo1—C3—C2	−131.25 (19)	C4—C9—C10—C8	176.00 (15)
C5ⁱ—Mo1—C3—C2	47.32 (19)	Mo1ⁱ—C9—C10—C8	53.20 (13)
C8ⁱ—Mo1—C3—C2	150.89 (12)	Mo1—C9—C10—C8	122.69 (14)
C1—Mo1—C3—C2	−28.78 (12)	C5—C9—C10—C1	−175.37 (15)
C9—Mo1—C3—C2	−101.53 (14)	C4—C9—C10—C1	0.4 (2)
C10ⁱ—Mo1—C3—C2	−178.82 (12)	Mo1ⁱ—C9—C10—C1	−122.43 (15)
C10—Mo1—C3—C2	−65.01 (13)	Mo1—C9—C10—C1	−52.93 (14)
C2—C3—C4—C9	−1.9 (3)	C5—C9—C10—Mo1ⁱ	−52.94 (13)
Mo1—C3—C4—C9	−57.84 (15)	C4—C9—C10—Mo1ⁱ	122.80 (14)
C2—C3—C4—Mo1	55.97 (17)	Mo1—C9—C10—Mo1ⁱ	69.50 (4)
C6ⁱ—Mo1—C4—C3	47.69 (19)	C5—C9—C10—Mo1	−122.43 (14)
C7ⁱ—Mo1—C4—C3	78.55 (14)	C4—C9—C10—Mo1	53.30 (13)
C2—Mo1—C4—C3	−29.87 (13)	Mo1ⁱ—C9—C10—Mo1	−69.50 (4)
C8ⁱ—Mo1—C4—C3	114.66 (13)	C6ⁱ—Mo1—C10—C8	67.8 (2)
C1—Mo1—C4—C3	−65.46 (13)	C3—Mo1—C10—C8	−177.41 (17)
C9ⁱ—Mo1—C4—C3	−178.45 (12)	C2—Mo1—C10—C8	145.24 (18)
C9—Mo1—C4—C3	−130.94 (18)	C4—Mo1—C10—C8	−141.19 (18)
C10ⁱ—Mo1—C4—C3	151.41 (12)	C5ⁱ—Mo1—C10—C8	39.17 (17)
C10—Mo1—C4—C3	−101.58 (14)	C8ⁱ—Mo1—C10—C8	−62.2 (2)
C6ⁱ—Mo1—C4—C9	178.64 (11)	C1—Mo1—C10—C8	116.7 (2)
C3—Mo1—C4—C9	130.94 (18)	C9ⁱ—Mo1—C10—C8	2.70 (17)
C7ⁱ—Mo1—C4—C9	−150.51 (11)	C9—Mo1—C10—C8	−111.65 (19)
C2—Mo1—C4—C9	101.07 (12)	C10ⁱ—Mo1—C10—C8	−33.67 (14)
C8ⁱ—Mo1—C4—C9	−114.40 (11)	C6ⁱ—Mo1—C10—C1	−48.81 (17)
C1—Mo1—C4—C9	65.49 (11)	C3—Mo1—C10—C1	65.93 (13)
C9ⁱ—Mo1—C4—C9	−47.50 (18)	C2—Mo1—C10—C1	28.59 (13)
C10ⁱ—Mo1—C4—C9	−77.64 (12)	C4—Mo1—C10—C1	102.16 (13)
C10—Mo1—C4—C9	29.36 (10)	C5ⁱ—Mo1—C10—C1	−77.49 (13)
C3—C4—C9—C5	176.78 (16)	C8ⁱ—Mo1—C10—C1	−178.89 (12)
Mo1—C4—C9—C5	120.50 (15)	C9ⁱ—Mo1—C10—C1	−113.95 (12)
C3—C4—C9—C10	1.2 (2)	C9—Mo1—C10—C1	131.69 (16)
Mo1—C4—C9—C10	−55.06 (13)	C10ⁱ—Mo1—C10—C1	−150.33 (13)
C3—C4—C9—Mo1ⁱ	89.3 (2)	C6ⁱ—Mo1—C10—C9	179.49 (11)
Mo1—C4—C9—Mo1ⁱ	33.05 (13)	C3—Mo1—C10—C9	−65.76 (11)
C3—C4—C9—Mo1	56.28 (16)	C2—Mo1—C10—C9	−103.11 (12)
C3—Mo1—C9—C5	−145.02 (17)	C4—Mo1—C10—C9	−29.54 (10)
C7ⁱ—Mo1—C9—C5	−66.2 (2)	C5ⁱ—Mo1—C10—C9	150.82 (10)
C2—Mo1—C9—C5	177.57 (17)	C8ⁱ—Mo1—C10—C9	49.42 (15)
C4—Mo1—C9—C5	−115.7 (2)	C1—Mo1—C10—C9	−131.69 (16)
C5ⁱ—Mo1—C9—C5	65.4 (2)	C9ⁱ—Mo1—C10—C9	114.35 (8)
C8ⁱ—Mo1—C9—C5	−37.40 (17)	C10ⁱ—Mo1—C10—C9	77.98 (9)
C1—Mo1—C9—C5	142.06 (17)	C6ⁱ—Mo1—C10—Mo1ⁱ	101.52 (11)
C9ⁱ—Mo1—C9—C5	35.70 (13)	C3—Mo1—C10—Mo1ⁱ	−143.74 (8)
C10ⁱ—Mo1—C9—C5	−1.05 (16)	C2—Mo1—C10—Mo1ⁱ	178.91 (8)
C10—Mo1—C9—C5	113.13 (19)	C4—Mo1—C10—Mo1ⁱ	−107.52 (7)
C3—Mo1—C9—C4	−29.28 (12)	C5ⁱ—Mo1—C10—Mo1ⁱ	72.84 (7)
C7ⁱ—Mo1—C9—C4	49.53 (16)	C8ⁱ—Mo1—C10—Mo1ⁱ	−28.56 (11)
C2—Mo1—C9—C4	−66.68 (12)	C1—Mo1—C10—Mo1ⁱ	150.33 (13)
C5ⁱ—Mo1—C9—C4	−178.88 (12)	C9ⁱ—Mo1—C10—Mo1ⁱ	36.37 (6)
C8ⁱ—Mo1—C9—C4	78.35 (12)	C9—Mo1—C10—Mo1ⁱ	−77.98 (9)
C1—Mo1—C9—C4	−102.19 (13)	C10ⁱ—Mo1—C10—Mo1ⁱ	0.0

Symmetry code: (i) −x+1, −y, −z+2.

Experimental details

Crystal data
Chemical formula	[Mo(C₁₀H₈)₂]
M_r	352.27
Crystal system, space group	Monoclinic, P2₁/n
Temperature (K)	173
a, b, c (Å)	8.4452 (10), 8.0716 (10), 10.9890 (13)
β (°)	109.186 (2)
V (Å³)	707.47 (15)
Z	2
Radiation type	Mo Kα
µ (mm⁻¹)	0.92
Crystal size (mm)	0.60 × 0.60 × 0.30

Data collection
Diffractometer	Bruker SMART Platform CCD diffractometer
Absorption correction	Multi-scan (SADABS; Bruker, 2003)
T_min, T_max	0.610, 0.771
No. of measured, independent and observed [I > 2σ(I)] reflections	8208, 1674, 1420
R_int	0.031
(sin θ/λ)_max (Å⁻¹)	0.658

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.028, 0.069, 1.03
No. of reflections	1674
No. of parameters	132
H-atom treatment	All H-atom parameters refined
Δρ_max, Δρ_min (e Å⁻³)	0.27, −0.28

Computer programs: SMART (Bruker, 2003), SAINT (Bruker, 2003), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), SHELXTL (Sheldrick, 2008).

Acknowledgements

The authors are grateful to the National Science Foundation program (grant CHE–0841014).

References

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