Tricarbonyl(chlorodiphenylstannyl){η5-[2-(dimethylamino)ethyl]cyclopenta­dienyl}molybdenum

Fischer, P.J.; Krohn, K.M.; Young, V.G. Jr

doi:10.1107/S1600536809014329

metal-organic compounds

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ISSN: 2056-9890

Volume 65| Part 5| May 2009| Pages m558-m559

doi:10.1107/S1600536809014329

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Tricarbonyl(chlorodiphenylstannyl){η⁵-[2-(dimethylamino)ethyl]cyclopentadienyl}molybdenum

Paul J. Fischer,^a ^* Kristina M. Krohn ^a and Victor G. Young Jr ^b

^aChemistry Department, Macalester College, 1600 Grand Avenue, Saint Paul, MN 55105, USA, and ^bX-ray Crystallographic Laboratory, Department of Chemistry, University of Minnesota, 207 Pleasant Street SE, Minneapolis, MN 55455, USA
^*Correspondence e-mail: fischer@macalester.edu

(Received 2 April 2009; accepted 16 April 2009; online 25 April 2009)

Reaction of the tricarbonyl{η⁵-[2-(dimethylamino)ethyl]cyclopentadienyl}molybdenum anion and dichloridodiphenylstannane affords the title compound, [MoSn(C₆H₅)₂Cl(C₉H₁₄N)(CO)₃], which exhibits a four-legged piano-stool geometry with chloridodiphenylstannyl ligands unperturbed by the pendant 2-(dimethylamino)ethyl groups. The Mo—Sn bond length [2.7584 (5) Å] and the distortion of the tetrahedral tin coordination geometry are similar to those observed in related tin-substituted tricarbonylmolybdenum and -tungsten complexes.

Related literature

The synthesis of Mo(SnMe₂Cl)(CO)₃(η⁵-Cp) was reported by Patil & Graham (1966 ). This methodolgy was extended to prepare Mo(SnPh₂Cl)(CO)₃(η⁵-Cp) by Marks & Seyam (1974 ). Triphenyltin and tricyclohexyltin derivatives of [M(CO)₃(η⁵-C₅H₄CH₂CH₂NMe₂)]⁻ (M = Mo and W) were reported by Fischer et al. (2005 ). The structural characterization and reaction chemistry of a variety of half-sandwich molybdenum and tungsten chlorostannyl complexes have been reported by Braunschweig et al. (2007 , 2009 ). The Lewis acidity of coordinatively saturated chlorostannyl ligands has been explored by Tang et al. (2005 ). Structural parameters that define four-legged piano-stool geometries were detailed by Kubácek et al. (1982 ).

Experimental

Crystal data

[MoSn(C₆H₅)₂Cl(C₉H₁₄N)(CO)₃]
M_r = 624.52
Triclinic, $[P \overline 1]$
a = 8.8096 (8) Å
b = 9.3458 (8) Å
c = 16.1258 (14) Å
α = 89.392 (2)°
β = 85.269 (2)°
γ = 63.8560 (10)°
V = 1187.29 (18) Å³
Z = 2
Mo Kα radiation
μ = 1.72 mm⁻¹
T = 173 K
0.25 × 0.12 × 0.04 mm

Data collection

Bruker SMART CCD area-detector diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2003 ) T_min = 0.673, T_max = 0.935
14425 measured reflections
5431 independent reflections
4081 reflections with I > 2σ(I)
R_int = 0.056

Refinement

R[F² > 2σ(F²)] = 0.036
wR(F²) = 0.083
S = 1.00
5431 reflections
282 parameters
H-atom parameters constrained
Δρ_max = 0.71 e Å⁻³
Δρ_min = −0.56 e Å⁻³

Table 1
Selected bond lengths (Å)

Sn1—C13	2.144 (4)
Sn1—C19	2.146 (4)
Sn1—Cl1	2.3914 (11)

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/S1600536809014329/si2168sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536809014329/si2168Isup2.hkl

checkCIF report

Comment top

The chemistry of half-sandwich molybdenum and tungsten chlorostannyl complexes is undergoing a revival since their discovery roughly forty years ago (Braunschweig et al., 2009). Chlorostannyl ligands permit functionalization at tin in heterobimetallic complexes (Braunschweig et al., 2007). The design of hypervalent tin ligands via intramolecular coordination of cyclopentadienyl-bound tethered donor groups is facilitated by chlorostannyl ligand Lewis acidity (Tang et al., 2005).

The complexes W(SnBu₂Cl)(CO)₃(η⁵-Cp) (2) and W(SnMe₂Cl)(CO)₃(η⁵-Cp*) (3) were structurally characterized by Braunschweig et al. (2007). The title complex 1 is the first crystallographically characterized substance of general formula M(SnAr₂X)(CO)₃(η⁵-Cp).

The Mo—Sn bond length in 1 is slightly shorter (Table 1) than the W—Sn distances found in 2 (2.7959 (5) Å) and 3 (2.7866 (3) Å), respectively. The steric impact of the SnPh₃ ligand relative to SnPh₂Cl is minimal on the basis of Mo—Sn bond lengths; this separation is 2.8152 (3) Å in Mo(SnPh₃)(CO)₃(η⁵-C₅H₄CH₂CH₂NMe₂) (4) (Fischer et al., 2005). The geometric parameters of 1-4 satisfy the requirements for four-legged piano-stool structures (Kubácek et al., 1982).

The tetrahedral coordination geometry of the tin atoms in 1-3 are distorted more significantly than that of 4. In 4, the diagnostic six angles about tin range from 105.60 (9)° to 116.15 (6)°, while the corresponding angles in 1 range from 100.30 (11)° to 120.34 (11)°. In 1-3 the M—Sn—C angles are widened whereas the C—Sn—Cl angles are more acute in comparison to the ideal tetrahedral angle. The angles about the Sn atoms of 1 and 3 are very similar as the phenyl and methyl substituents, respectively, attempt to minimize steric hinderance with the M(CO)₃(Cp) fragment. The C(13)—Sn(1)—Mo (116.32 (10)°) and C(19)—Sn(1)—Mo (120.34 (11)°) angles in 1 are similar to the corresponding angles found in 3 (118.56 (11), 118.31 (12)°). The widening of these angles is accommodated by compression of C—Sn—Cl angles. These angles in 1 (C(13)—Sn(1)—Cl(1), 100.30 (11)°; C(19)—Sn(1)—Cl(1), 101.25 (11)°) are similar to the corresponding angles found in 3 (99.75 (12), 100.48 (13)°).

Related literature top

The synthesis of Mo(SnMe₂Cl)(CO)₃(η⁵-Cp) was reported by Patil & Graham (1966). This methodolgy was extended to prepare Mo(SnPh₂Cl)(CO)₃(η⁵-Cp) by Marks & Seyam (1974). Triphenyltin and tricyclohexyltin derivatives of [M(CO)₃(η⁵-C₅H₄CH₂CH₂NMe₂)]^- (M = Mo and W) were reported by Fischer et al. (2005). The structural characterization and reaction chemistry of a variety of half-sandwich molybdenum and tungsten chlorostannyl complexes have been reported by Braunschweig et al. (2007, 2009). The Lewis acidity of coordinatively saturated chlorostannyl ligands has been explored by Tang et al. (2005). Structural parameters that define four-legged piano-stool geometries were detailed by Kubácek et al. (1982).

Experimental top

The following procedures were conducted under argon using standard techniques for handling air and moisture sensitive substances. THF (75 ml) was added to molybdenum hexacarbonyl (0.415 g, 1.57 mmol) and sodium ((2-dimethylamino)ethyl)cyclopentadienide (0.300 g, 1.88 mmol). The yellow solution was refluxed for 15 h. Addition of dichlorodiphenylstannane (0.540 g, 1.57 mmol) in THF (30 ml) resulted in a pale yellow suspension. A single molybdenum carbonyl complex was present in solution (based on IR spectroscopy) within 10 min. The suspension was filtered through Celite. THF was removed in vacuo revealing a yellow oil. The product was extracted with pentane (5 * 70 ml). Each colorless extract was filtered. The combined extracts were concentrated in vacuo until a yellow solid precipitated. The suspension (75 ml) was cooled and filtered at -70°C. The pale yellow, moderately air-sensitive solid was washed with pentane (-60°C, 5 * 15 ml) and dried in vacuo. Recrystallization from pentane at -65°C afforded pale yellow microcrystals (0.461 g, 47%). X-ray quality single crystals of 1 were obtained from a supersaturated pentane solution.

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 1 (50% thermal ellipsoids).

Tricarbonyl-1κ³C-chlorido-2κCl-diphenyl-2κ²C- {1η⁵-[2-(dimethylamino)ethyl]cyclopentadienyl}molybdenum(0) tin(IV)(Mo—Sn) top

Crystal data top

[MoSn(C₆H₅)₂Cl(C₉H₁₄N)(CO)₃]	Z = 2
M_r = 624.52	F(000) = 616
Triclinic, P1	D_x = 1.747 Mg m⁻³
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 8.8096 (8) Å	Cell parameters from 2659 reflections
b = 9.3458 (8) Å	θ = 2.4–27.4°
c = 16.1258 (14) Å	µ = 1.72 mm⁻¹
α = 89.392 (2)°	T = 173 K
β = 85.269 (2)°	Plate, colourless
γ = 63.856 (1)°	0.25 × 0.12 × 0.04 mm
V = 1187.29 (18) Å³

Data collection top

Bruker SMART CCD area-detector diffractometer	5431 independent reflections
Radiation source: sealed tube	4081 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.056
ϕ and ω scans	θ_max = 27.5°, θ_min = 2.4°
Absorption correction: multi-scan (SADABS; Bruker, 2003)	h = −11→11
T_min = 0.673, T_max = 0.935	k = −12→12
14425 measured reflections	l = 0→20

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)] = 0.036	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.083	H-atom parameters constrained
S = 1.00	w = 1/[σ²(F_o²) + (0.0315P)²] where P = (F_o² + 2F_c²)/3
5431 reflections	(Δ/σ)_max = 0.001
282 parameters	Δρ_max = 0.71 e Å⁻³
0 restraints	Δρ_min = −0.56 e Å⁻³

Crystal data top

[MoSn(C₆H₅)₂Cl(C₉H₁₄N)(CO)₃]	γ = 63.856 (1)°
M_r = 624.52	V = 1187.29 (18) Å³
Triclinic, P1	Z = 2
a = 8.8096 (8) Å	Mo Kα radiation
b = 9.3458 (8) Å	µ = 1.72 mm⁻¹
c = 16.1258 (14) Å	T = 173 K
α = 89.392 (2)°	0.25 × 0.12 × 0.04 mm
β = 85.269 (2)°

Data collection top

Bruker SMART CCD area-detector diffractometer	5431 independent reflections
Absorption correction: multi-scan (SADABS; Bruker, 2003)	4081 reflections with I > 2σ(I)
T_min = 0.673, T_max = 0.935	R_int = 0.056
14425 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.036	0 restraints
wR(F²) = 0.083	H-atom parameters constrained
S = 1.00	Δρ_max = 0.71 e Å⁻³
5431 reflections	Δρ_min = −0.56 e Å⁻³
282 parameters

Special details top

Experimental. Anal. Calcd for C₂₄H₂₄ClMoNO₃Sn: C, 46.15; H, 3.87; N, 2.24. Found: C, 46.01, H, 3.78; N, 2.30.

IR (THF) ν(CO): 2011 (s), 1944 (m, sh), 1912 (s) cm^-1; (pentane) ν(CO): 2015 (s), 1952 (m), 1919 (m) cm^-1; (nujol) ν(CO): 2011 (s), 1942 (m, sh), 1893 (s) cm^-1.

NMR (CD₂Cl₂, 300 MHz) ¹H δ 7.78–7.54 (m, 4H, ortho, SnPh₂Cl), 7.48–7.32 (m, 6H, meta/para, SnPh₂Cl), 5.52 (app. t, J=2.1 Hz, 2H, Cp), 5.27 (app. t, J=2.1 Hz, 2H, Cp), 2.44–2.29 (m, 4H, CH₂CH₂), 2.14 (s, 6H, CH₃).

NMR (CD₂Cl₂, 75.5 MHz) ¹³C{¹H} δ 228.64 (s, trans CO), 224.35 (s, cis CO), 146.11 (s, ipso C), 135.30 (s, ortho C, ^117,119Sn-¹³C sat. (merged): 135.63, 134.97, ²J_SnC=49.7 Hz), 129.80 (s, para, ^117,119Sn-¹³C sat. (merged): 129.89, 129.73, ⁴J_SnC=12.2 Hz), 129.12 (s, meta C, ^117,119Sn-¹³C sat. (merged): 129.48, 128.76, ³J_SnC=54.5 Hz), 114.60 (s, quat. C, Cp), 91.75 (s, Cp), 89.65 (s, Cp), 61.15 (s, CH₂CH₂N(CH₃)₂), 45.57 (s, CH₂CH₂N(CH₃)₂), 27.08 (s, CH₂CH₂N(CH₃)₂).

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. A crystal (approximate dimensions 1/4 x 0.12 x 0.04 mm³) was placed onto the tip of a 0.1 mm diameter glass capillary and mounted on a CCD area detector diffractometer for a data collection at 173 (2) K (SMART, Bruker, 2003). A preliminary set of cell constants was calculated from reflections harvested from three sets of 20 frames. These initial sets of frames were oriented such that orthogonal wedges of reciprocal space were surveyed. This produced initial orientation matrices determined from 48 reflections. The data collection was carried out using Mo Kα radiation (graphite monochromator) with a frame time of 8 s and a detector distance of 4.8 cm. A randomly oriented region of reciprocal space was surveyed to the extent of one sphere and to a resolution of 0.77 Å. Four major sections of frames were collected with 0.30° steps in ω at four different ϕ settings and a detector position of -28° in 2θ. The intensity data were corrected for absorption and decay (SADABS, Bruker, 2003). Final cell constants were calculated from 2659 strong reflections from the actual data collection after integration (SAINT, Bruker, 2003).

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
Mo1	0.58741 (4)	0.72843 (4)	0.66247 (2)	0.01938 (9)
C1	0.6228 (5)	0.6492 (5)	0.5449 (3)	0.0282 (9)
O1	0.6433 (4)	0.6021 (4)	0.47726 (19)	0.0434 (8)
C2	0.8374 (5)	0.6518 (5)	0.6404 (3)	0.0265 (9)
O2	0.9820 (4)	0.5983 (4)	0.6286 (2)	0.0420 (8)
C3	0.4662 (5)	0.9349 (5)	0.6085 (2)	0.0223 (9)
O3	0.3862 (3)	1.0542 (3)	0.57849 (17)	0.0279 (7)
C4	0.6083 (5)	0.5692 (5)	0.7791 (2)	0.0242 (9)
C5	0.5505 (5)	0.5124 (5)	0.7139 (3)	0.0267 (9)
H5A	0.6093	0.4105	0.6868	0.032*
C6	0.3894 (6)	0.6330 (5)	0.6953 (3)	0.0353 (11)
H6A	0.3222	0.6263	0.6538	0.042*
C7	0.3483 (5)	0.7632 (5)	0.7495 (3)	0.0338 (11)
H7A	0.2470	0.8602	0.7514	0.041*
C8	0.4815 (5)	0.7269 (5)	0.8010 (2)	0.0267 (9)
H8A	0.4862	0.7953	0.8428	0.032*
C9	0.7613 (5)	0.4754 (5)	0.8262 (3)	0.0273 (9)
H9A	0.8019	0.5484	0.8498	0.033*
H9B	0.8542	0.3974	0.7881	0.033*
C10	0.7123 (5)	0.3881 (5)	0.8963 (3)	0.0296 (10)
H10A	0.6087	0.4656	0.9289	0.035*
H10B	0.6844	0.3072	0.8714	0.035*
N1	0.8441 (4)	0.3094 (4)	0.9527 (2)	0.0262 (8)
C11	0.9863 (5)	0.1694 (5)	0.9137 (3)	0.0304 (10)
H11A	1.0350	0.2008	0.8641	0.046*
H11B	0.9466	0.0916	0.8977	0.046*
H11C	1.0730	0.1215	0.9531	0.046*
C12	0.7735 (6)	0.2630 (5)	1.0275 (3)	0.0370 (11)
H12A	0.6813	0.3579	1.0552	0.055*
H12B	0.8626	0.2116	1.0654	0.055*
H12C	0.7293	0.1883	1.0121	0.055*
Sn1	0.66959 (3)	0.95053 (3)	0.732290 (16)	0.02009 (8)
Cl1	0.86682 (14)	0.82366 (13)	0.83383 (7)	0.0336 (3)
C13	0.4703 (5)	1.1368 (5)	0.8078 (2)	0.0235 (9)
C14	0.4566 (6)	1.1328 (5)	0.8939 (3)	0.0321 (10)
H14A	0.5345	1.0426	0.9209	0.038*
C15	0.3298 (6)	1.2593 (6)	0.9416 (3)	0.0418 (12)
H15A	0.3210	1.2541	1.0005	0.050*
C16	0.2193 (6)	1.3896 (6)	0.9037 (3)	0.0450 (13)
H16A	0.1352	1.4767	0.9364	0.054*
C17	0.2282 (6)	1.3965 (5)	0.8176 (3)	0.0396 (12)
H17A	0.1492	1.4872	0.7914	0.047*
C18	0.3534 (5)	1.2702 (5)	0.7697 (3)	0.0301 (10)
H18A	0.3592	1.2747	0.7107	0.036*
C19	0.7998 (5)	1.0601 (4)	0.6573 (2)	0.0234 (9)
C20	0.7633 (6)	1.1042 (5)	0.5768 (3)	0.0353 (11)
H20A	0.6844	1.0783	0.5517	0.042*
C21	0.8401 (6)	1.1859 (6)	0.5316 (3)	0.0410 (12)
H21A	0.8138	1.2145	0.4760	0.049*
C22	0.9535 (6)	1.2252 (5)	0.5667 (3)	0.0379 (12)
H22A	1.0046	1.2824	0.5360	0.045*
C23	0.9928 (6)	1.1815 (5)	0.6468 (3)	0.0347 (11)
H23A	1.0730	1.2068	0.6711	0.042*
C24	0.9161 (5)	1.1009 (5)	0.6922 (3)	0.0286 (10)
H24A	0.9428	1.0728	0.7477	0.034*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Mo1	0.02176 (19)	0.01690 (18)	0.01947 (19)	−0.00855 (15)	−0.00209 (14)	0.00347 (14)
C1	0.035 (3)	0.022 (2)	0.028 (2)	−0.012 (2)	−0.0045 (19)	0.0042 (18)
O1	0.061 (2)	0.0359 (19)	0.0279 (18)	−0.0161 (17)	−0.0040 (16)	−0.0046 (15)
C2	0.030 (2)	0.022 (2)	0.028 (2)	−0.0111 (19)	−0.0049 (19)	0.0037 (17)
O2	0.0278 (18)	0.045 (2)	0.048 (2)	−0.0117 (16)	0.0004 (15)	−0.0022 (16)
C3	0.027 (2)	0.026 (2)	0.016 (2)	−0.0140 (19)	−0.0008 (17)	−0.0027 (17)
O3	0.0258 (16)	0.0235 (15)	0.0288 (16)	−0.0053 (13)	−0.0058 (13)	0.0093 (13)
C4	0.023 (2)	0.024 (2)	0.027 (2)	−0.0111 (18)	−0.0017 (17)	0.0083 (17)
C5	0.032 (2)	0.019 (2)	0.035 (2)	−0.0164 (19)	−0.0063 (19)	0.0107 (18)
C6	0.031 (2)	0.042 (3)	0.042 (3)	−0.023 (2)	−0.013 (2)	0.023 (2)
C7	0.021 (2)	0.033 (3)	0.039 (3)	−0.005 (2)	0.0062 (19)	0.014 (2)
C8	0.033 (2)	0.025 (2)	0.020 (2)	−0.0130 (19)	0.0052 (18)	0.0064 (17)
C9	0.032 (2)	0.026 (2)	0.029 (2)	−0.018 (2)	−0.0093 (19)	0.0076 (18)
C10	0.026 (2)	0.029 (2)	0.034 (2)	−0.0116 (19)	−0.0073 (19)	0.0117 (19)
N1	0.0263 (19)	0.0221 (18)	0.0282 (19)	−0.0085 (15)	−0.0057 (15)	0.0090 (15)
C11	0.034 (3)	0.022 (2)	0.034 (3)	−0.010 (2)	−0.009 (2)	0.0043 (18)
C12	0.042 (3)	0.036 (3)	0.029 (2)	−0.015 (2)	−0.002 (2)	0.014 (2)
Sn1	0.02179 (15)	0.01760 (14)	0.02049 (15)	−0.00814 (12)	−0.00317 (11)	0.00216 (11)
Cl1	0.0381 (6)	0.0298 (6)	0.0355 (6)	−0.0152 (5)	−0.0179 (5)	0.0096 (5)
C13	0.024 (2)	0.022 (2)	0.027 (2)	−0.0132 (18)	0.0016 (17)	−0.0024 (17)
C14	0.037 (3)	0.032 (2)	0.027 (2)	−0.016 (2)	−0.001 (2)	−0.0019 (19)
C15	0.047 (3)	0.051 (3)	0.030 (3)	−0.026 (3)	0.011 (2)	−0.012 (2)
C16	0.038 (3)	0.038 (3)	0.055 (3)	−0.018 (2)	0.023 (2)	−0.024 (3)
C17	0.034 (3)	0.022 (2)	0.058 (3)	−0.009 (2)	0.003 (2)	−0.002 (2)
C18	0.032 (2)	0.023 (2)	0.034 (2)	−0.013 (2)	0.0053 (19)	−0.0018 (19)
C19	0.021 (2)	0.019 (2)	0.027 (2)	−0.0069 (17)	0.0012 (17)	0.0003 (17)
C20	0.037 (3)	0.042 (3)	0.032 (3)	−0.021 (2)	−0.010 (2)	0.008 (2)
C21	0.050 (3)	0.053 (3)	0.026 (2)	−0.028 (3)	−0.003 (2)	0.011 (2)
C22	0.042 (3)	0.030 (2)	0.041 (3)	−0.019 (2)	0.016 (2)	0.001 (2)
C23	0.030 (2)	0.034 (3)	0.044 (3)	−0.020 (2)	0.006 (2)	−0.006 (2)
C24	0.025 (2)	0.029 (2)	0.030 (2)	−0.0112 (19)	−0.0011 (18)	−0.0022 (19)

Geometric parameters (Å, º) top

Mo1—C3	1.981 (4)	C11—H11B	0.9800
Mo1—C1	1.992 (4)	C11—H11C	0.9800
Mo1—C2	1.994 (4)	C12—H12A	0.9800
Mo1—C6	2.308 (4)	C12—H12B	0.9800
Mo1—C5	2.317 (4)	C12—H12C	0.9800
Mo1—C7	2.331 (4)	Sn1—C13	2.144 (4)
Mo1—C8	2.351 (4)	Sn1—C19	2.146 (4)
Mo1—C4	2.353 (4)	Sn1—Cl1	2.3914 (11)
Mo1—Sn1	2.7584 (5)	C13—C14	1.384 (6)
C1—O1	1.150 (5)	C13—C18	1.396 (6)
C2—O2	1.145 (5)	C14—C15	1.397 (6)
C3—O3	1.152 (4)	C14—H14A	0.9500
C4—C5	1.408 (6)	C15—C16	1.357 (7)
C4—C8	1.428 (5)	C15—H15A	0.9500
C4—C9	1.509 (5)	C16—C17	1.386 (7)
C5—C6	1.424 (6)	C16—H16A	0.9500
C5—H5A	0.9500	C17—C18	1.392 (6)
C6—C7	1.399 (6)	C17—H17A	0.9500
C6—H6A	0.9500	C18—H18A	0.9500
C7—C8	1.409 (6)	C19—C20	1.379 (6)
C7—H7A	0.9500	C19—C24	1.398 (5)
C8—H8A	0.9500	C20—C21	1.390 (6)
C9—C10	1.530 (5)	C20—H20A	0.9500
C9—H9A	0.9900	C21—C22	1.369 (6)
C9—H9B	0.9900	C21—H21A	0.9500
C10—N1	1.457 (5)	C22—C23	1.376 (6)
C10—H10A	0.9900	C22—H22A	0.9500
C10—H10B	0.9900	C23—C24	1.384 (6)
N1—C11	1.456 (5)	C23—H23A	0.9500
N1—C12	1.461 (5)	C24—H24A	0.9500
C11—H11A	0.9800

C3—Mo1—C1	81.02 (16)	C4—C9—C10	109.1 (3)
C3—Mo1—C2	109.86 (16)	C4—C9—H9A	109.9
C1—Mo1—C2	79.28 (17)	C10—C9—H9A	109.9
C3—Mo1—C6	106.33 (16)	C4—C9—H9B	109.9
C1—Mo1—C6	91.77 (17)	C10—C9—H9B	109.9
C2—Mo1—C6	140.66 (16)	H9A—C9—H9B	108.3
C3—Mo1—C5	141.90 (15)	N1—C10—C9	114.0 (3)
C1—Mo1—C5	93.04 (16)	N1—C10—H10A	108.8
C2—Mo1—C5	105.82 (15)	C9—C10—H10A	108.8
C6—Mo1—C5	35.87 (14)	N1—C10—H10B	108.8
C3—Mo1—C7	92.95 (15)	C9—C10—H10B	108.8
C1—Mo1—C7	122.26 (17)	H10A—C10—H10B	107.6
C2—Mo1—C7	151.56 (16)	C11—N1—C10	112.1 (3)
C6—Mo1—C7	35.08 (16)	C11—N1—C12	109.4 (3)
C5—Mo1—C7	58.61 (15)	C10—N1—C12	110.0 (3)
C3—Mo1—C8	113.36 (15)	N1—C11—H11A	109.5
C1—Mo1—C8	149.29 (16)	N1—C11—H11B	109.5
C2—Mo1—C8	117.21 (16)	H11A—C11—H11B	109.5
C6—Mo1—C8	58.71 (16)	N1—C11—H11C	109.5
C5—Mo1—C8	58.52 (15)	H11A—C11—H11C	109.5
C7—Mo1—C8	35.02 (15)	H11B—C11—H11C	109.5
C3—Mo1—C4	148.50 (15)	N1—C12—H12A	109.5
C1—Mo1—C4	124.20 (15)	N1—C12—H12B	109.5
C2—Mo1—C4	94.55 (15)	H12A—C12—H12B	109.5
C6—Mo1—C4	59.16 (14)	N1—C12—H12C	109.5
C5—Mo1—C4	35.09 (14)	H12A—C12—H12C	109.5
C7—Mo1—C4	58.64 (14)	H12B—C12—H12C	109.5
C8—Mo1—C4	35.36 (13)	C13—Sn1—C19	106.86 (14)
C3—Mo1—Sn1	71.39 (11)	C13—Sn1—Cl1	100.30 (11)
C1—Mo1—Sn1	129.99 (12)	C19—Sn1—Cl1	101.25 (11)
C2—Mo1—Sn1	72.45 (11)	C13—Sn1—Mo1	116.32 (10)
C6—Mo1—Sn1	135.31 (13)	C19—Sn1—Mo1	120.34 (11)
C5—Mo1—Sn1	133.76 (11)	Cl1—Sn1—Mo1	108.86 (3)
C7—Mo1—Sn1	100.50 (12)	C14—C13—C18	118.4 (4)
C8—Mo1—Sn1	80.70 (10)	C14—C13—Sn1	122.3 (3)
C4—Mo1—Sn1	98.79 (10)	C18—C13—Sn1	119.3 (3)
O1—C1—Mo1	179.4 (4)	C13—C14—C15	121.0 (4)
O2—C2—Mo1	175.7 (4)	C13—C14—H14A	119.5
O3—C3—Mo1	175.6 (3)	C15—C14—H14A	119.5
C5—C4—C8	107.1 (4)	C16—C15—C14	120.0 (4)
C5—C4—C9	127.1 (4)	C16—C15—H15A	120.0
C8—C4—C9	125.3 (4)	C14—C15—H15A	120.0
C5—C4—Mo1	71.0 (2)	C15—C16—C17	120.5 (4)
C8—C4—Mo1	72.2 (2)	C15—C16—H16A	119.8
C9—C4—Mo1	128.7 (3)	C17—C16—H16A	119.8
C4—C5—C6	108.7 (4)	C16—C17—C18	119.8 (4)
C4—C5—Mo1	73.9 (2)	C16—C17—H17A	120.1
C6—C5—Mo1	71.7 (2)	C18—C17—H17A	120.1
C4—C5—H5A	125.7	C17—C18—C13	120.4 (4)
C6—C5—H5A	125.7	C17—C18—H18A	119.8
Mo1—C5—H5A	120.5	C13—C18—H18A	119.8
C7—C6—C5	107.4 (4)	C20—C19—C24	117.8 (4)
C7—C6—Mo1	73.4 (2)	C20—C19—Sn1	122.2 (3)
C5—C6—Mo1	72.4 (2)	C24—C19—Sn1	119.8 (3)
C7—C6—H6A	126.3	C19—C20—C21	121.1 (4)
C5—C6—H6A	126.3	C19—C20—H20A	119.4
Mo1—C6—H6A	119.8	C21—C20—H20A	119.4
C6—C7—C8	108.9 (4)	C22—C21—C20	120.4 (4)
C6—C7—Mo1	71.6 (2)	C22—C21—H21A	119.8
C8—C7—Mo1	73.2 (2)	C20—C21—H21A	119.8
C6—C7—H7A	125.5	C21—C22—C23	119.6 (4)
C8—C7—H7A	125.5	C21—C22—H22A	120.2
Mo1—C7—H7A	121.3	C23—C22—H22A	120.2
C7—C8—C4	107.9 (4)	C22—C23—C24	120.3 (4)
C7—C8—Mo1	71.7 (2)	C22—C23—H23A	119.9
C4—C8—Mo1	72.4 (2)	C24—C23—H23A	119.9
C7—C8—H8A	126.0	C23—C24—C19	120.9 (4)
C4—C8—H8A	126.0	C23—C24—H24A	119.6
Mo1—C8—H8A	121.5	C19—C24—H24A	119.6

C3—Mo1—C1—O1	−152 (36)	C4—Mo1—C7—C6	−79.8 (3)
C2—Mo1—C1—O1	96 (36)	Sn1—Mo1—C7—C6	−173.8 (2)
C6—Mo1—C1—O1	−46 (36)	C3—Mo1—C7—C8	−128.2 (3)
C5—Mo1—C1—O1	−10 (36)	C1—Mo1—C7—C8	150.6 (2)
C7—Mo1—C1—O1	−64 (36)	C2—Mo1—C7—C8	15.9 (5)
C8—Mo1—C1—O1	−31 (36)	C6—Mo1—C7—C8	117.2 (4)
C4—Mo1—C1—O1	7 (36)	C5—Mo1—C7—C8	78.7 (3)
Sn1—Mo1—C1—O1	152 (36)	C4—Mo1—C7—C8	37.4 (2)
C3—Mo1—C2—O2	−157 (5)	Sn1—Mo1—C7—C8	−56.6 (2)
C1—Mo1—C2—O2	−81 (5)	C6—C7—C8—C4	−0.8 (4)
C6—Mo1—C2—O2	−1 (5)	Mo1—C7—C8—C4	−63.9 (3)
C5—Mo1—C2—O2	9 (5)	C6—C7—C8—Mo1	63.1 (3)
C7—Mo1—C2—O2	61 (5)	C5—C4—C8—C7	0.5 (4)
C8—Mo1—C2—O2	72 (5)	C9—C4—C8—C7	−171.4 (4)
C4—Mo1—C2—O2	43 (5)	Mo1—C4—C8—C7	63.4 (3)
Sn1—Mo1—C2—O2	141 (5)	C5—C4—C8—Mo1	−62.9 (3)
C1—Mo1—C3—O3	98 (4)	C9—C4—C8—Mo1	125.2 (4)
C2—Mo1—C3—O3	173 (4)	C3—Mo1—C8—C7	58.8 (3)
C6—Mo1—C3—O3	9 (4)	C1—Mo1—C8—C7	−54.5 (4)
C5—Mo1—C3—O3	14 (4)	C2—Mo1—C8—C7	−171.6 (3)
C7—Mo1—C3—O3	−24 (4)	C6—Mo1—C8—C7	−36.7 (2)
C8—Mo1—C3—O3	−54 (4)	C5—Mo1—C8—C7	−79.0 (3)
C4—Mo1—C3—O3	−48 (4)	C4—Mo1—C8—C7	−116.4 (4)
Sn1—Mo1—C3—O3	−125 (4)	Sn1—Mo1—C8—C7	123.7 (2)
C3—Mo1—C4—C5	107.3 (3)	C3—Mo1—C8—C4	175.1 (2)
C1—Mo1—C4—C5	−31.1 (3)	C1—Mo1—C8—C4	61.9 (4)
C2—Mo1—C4—C5	−111.3 (3)	C2—Mo1—C8—C4	−55.2 (3)
C6—Mo1—C4—C5	37.6 (3)	C6—Mo1—C8—C4	79.6 (3)
C7—Mo1—C4—C5	78.8 (3)	C5—Mo1—C8—C4	37.3 (2)
C8—Mo1—C4—C5	115.9 (3)	C7—Mo1—C8—C4	116.4 (4)
Sn1—Mo1—C4—C5	175.8 (2)	Sn1—Mo1—C8—C4	−119.9 (2)
C3—Mo1—C4—C8	−8.6 (4)	C5—C4—C9—C10	−84.0 (5)
C1—Mo1—C4—C8	−147.0 (3)	C8—C4—C9—C10	86.2 (5)
C2—Mo1—C4—C8	132.9 (3)	Mo1—C4—C9—C10	−178.8 (3)
C6—Mo1—C4—C8	−78.2 (3)	C4—C9—C10—N1	−172.7 (3)
C5—Mo1—C4—C8	−115.9 (3)	C9—C10—N1—C11	−71.6 (4)
C7—Mo1—C4—C8	−37.0 (2)	C9—C10—N1—C12	166.5 (4)
Sn1—Mo1—C4—C8	60.0 (2)	C3—Mo1—Sn1—C13	69.08 (17)
C3—Mo1—C4—C9	−129.9 (4)	C1—Mo1—Sn1—C13	129.3 (2)
C1—Mo1—C4—C9	91.7 (4)	C2—Mo1—Sn1—C13	−172.07 (17)
C2—Mo1—C4—C9	11.6 (4)	C6—Mo1—Sn1—C13	−25.59 (19)
C6—Mo1—C4—C9	160.4 (4)	C5—Mo1—Sn1—C13	−76.73 (19)
C5—Mo1—C4—C9	122.8 (5)	C7—Mo1—Sn1—C13	−20.51 (16)
C7—Mo1—C4—C9	−158.3 (4)	C8—Mo1—Sn1—C13	−49.54 (16)
C8—Mo1—C4—C9	−121.3 (5)	C4—Mo1—Sn1—C13	−80.05 (15)
Sn1—Mo1—C4—C9	−61.3 (4)	C3—Mo1—Sn1—C19	−62.57 (17)
C8—C4—C5—C6	−0.1 (4)	C1—Mo1—Sn1—C19	−2.39 (19)
C9—C4—C5—C6	171.6 (4)	C2—Mo1—Sn1—C19	56.28 (17)
Mo1—C4—C5—C6	−63.8 (3)	C6—Mo1—Sn1—C19	−157.24 (19)
C8—C4—C5—Mo1	63.7 (3)	C5—Mo1—Sn1—C19	151.62 (19)
C9—C4—C5—Mo1	−124.6 (4)	C7—Mo1—Sn1—C19	−152.15 (16)
C3—Mo1—C5—C4	−126.0 (3)	C8—Mo1—Sn1—C19	178.81 (16)
C1—Mo1—C5—C4	154.7 (3)	C4—Mo1—Sn1—C19	148.31 (16)
C2—Mo1—C5—C4	74.9 (3)	C3—Mo1—Sn1—Cl1	−178.60 (12)
C6—Mo1—C5—C4	−116.5 (4)	C1—Mo1—Sn1—Cl1	−118.42 (16)
C7—Mo1—C5—C4	−78.9 (3)	C2—Mo1—Sn1—Cl1	−59.75 (12)
C8—Mo1—C5—C4	−37.6 (2)	C6—Mo1—Sn1—Cl1	86.73 (15)
Sn1—Mo1—C5—C4	−5.7 (3)	C5—Mo1—Sn1—Cl1	35.59 (15)
C3—Mo1—C5—C6	−9.5 (4)	C7—Mo1—Sn1—Cl1	91.81 (11)
C1—Mo1—C5—C6	−88.8 (3)	C8—Mo1—Sn1—Cl1	62.78 (11)
C2—Mo1—C5—C6	−168.5 (3)	C4—Mo1—Sn1—Cl1	32.28 (10)
C7—Mo1—C5—C6	37.6 (3)	C19—Sn1—C13—C14	−123.0 (3)
C8—Mo1—C5—C6	78.9 (3)	Cl1—Sn1—C13—C14	−17.8 (3)
C4—Mo1—C5—C6	116.5 (4)	Mo1—Sn1—C13—C14	99.3 (3)
Sn1—Mo1—C5—C6	110.8 (3)	C19—Sn1—C13—C18	54.6 (3)
C4—C5—C6—C7	−0.4 (5)	Cl1—Sn1—C13—C18	159.8 (3)
Mo1—C5—C6—C7	−65.5 (3)	Mo1—Sn1—C13—C18	−83.1 (3)
C4—C5—C6—Mo1	65.1 (3)	C18—C13—C14—C15	−0.5 (6)
C3—Mo1—C6—C7	−71.1 (3)	Sn1—C13—C14—C15	177.1 (3)
C1—Mo1—C6—C7	−152.3 (3)	C13—C14—C15—C16	−0.9 (7)
C2—Mo1—C6—C7	132.6 (3)	C14—C15—C16—C17	1.7 (7)
C5—Mo1—C6—C7	115.0 (4)	C15—C16—C17—C18	−1.2 (7)
C8—Mo1—C6—C7	36.7 (2)	C16—C17—C18—C13	−0.2 (7)
C4—Mo1—C6—C7	78.2 (3)	C14—C13—C18—C17	1.1 (6)
Sn1—Mo1—C6—C7	8.7 (3)	Sn1—C13—C18—C17	−176.6 (3)
C3—Mo1—C6—C5	173.9 (3)	C13—Sn1—C19—C20	−96.5 (4)
C1—Mo1—C6—C5	92.7 (3)	Cl1—Sn1—C19—C20	158.9 (3)
C2—Mo1—C6—C5	17.6 (4)	Mo1—Sn1—C19—C20	39.0 (4)
C7—Mo1—C6—C5	−115.0 (4)	C13—Sn1—C19—C24	78.2 (3)
C8—Mo1—C6—C5	−78.3 (3)	Cl1—Sn1—C19—C24	−26.4 (3)
C4—Mo1—C6—C5	−36.8 (2)	Mo1—Sn1—C19—C24	−146.3 (3)
Sn1—Mo1—C6—C5	−106.3 (3)	C24—C19—C20—C21	0.3 (7)
C5—C6—C7—C8	0.7 (5)	Sn1—C19—C20—C21	175.1 (3)
Mo1—C6—C7—C8	−64.2 (3)	C19—C20—C21—C22	−0.4 (7)
C5—C6—C7—Mo1	64.9 (3)	C20—C21—C22—C23	0.9 (7)
C3—Mo1—C7—C6	114.6 (3)	C21—C22—C23—C24	−1.2 (7)
C1—Mo1—C7—C6	33.4 (3)	C22—C23—C24—C19	1.0 (6)
C2—Mo1—C7—C6	−101.3 (4)	C20—C19—C24—C23	−0.6 (6)
C5—Mo1—C7—C6	−38.5 (2)	Sn1—C19—C24—C23	−175.5 (3)
C8—Mo1—C7—C6	−117.2 (4)

Experimental details

Crystal data
Chemical formula	[MoSn(C₆H₅)₂Cl(C₉H₁₄N)(CO)₃]
M_r	624.52
Crystal system, space group	Triclinic, P1
Temperature (K)	173
a, b, c (Å)	8.8096 (8), 9.3458 (8), 16.1258 (14)
α, β, γ (°)	89.392 (2), 85.269 (2), 63.856 (1)
V (Å³)	1187.29 (18)
Z	2
Radiation type	Mo Kα
µ (mm⁻¹)	1.72
Crystal size (mm)	0.25 × 0.12 × 0.04

Data collection
Diffractometer	Bruker SMART CCD area-detector diffractometer
Absorption correction	Multi-scan (SADABS; Bruker, 2003)
T_min, T_max	0.673, 0.935
No. of measured, independent and observed [I > 2σ(I)] reflections	14425, 5431, 4081
R_int	0.056
(sin θ/λ)_max (Å⁻¹)	0.650

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.036, 0.083, 1.00
No. of reflections	5431
No. of parameters	282
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.71, −0.56

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

Selected bond lengths (Å) top

Mo1—Sn1	2.7584 (5)	Sn1—C19	2.146 (4)
Sn1—C13	2.144 (4)	Sn1—Cl1	2.3914 (11)

Acknowledgements

The donors of the Petroleum Research Fund, administered by the American Chemical Society (grant No. ACS-PRF 46626-B), and an award from Research Corporation (grant No. CC5932) supported this research.

References

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