Tri­carbonyl­iodo(η⁵-methyl­cyclo­penta­dienyl)­tungsten

The title complex, [W(η⁵-C₅H₅CH₃)I(CO)₃], lies on a crystallographic mirror plane, with only one half-mol­ecule per asymmetric unit. This four-legged piano-stool tungsten complex is strained at the W atom, with the trans-C—W—I angle [130.93 (18)°] larger than the cis-C—W—C angle [111.1 (3)°]. A possible trans influence due to a larger π back-bonding is marginal, with an insignificant difference between the W—C bond length trans to I [1.984 (6) Å] and the other W—C_CO bond lengths [1.996 (5) Å].

Key indicators

• Single-crystal X-ray study
• T = 293 K
• Mean [sigma](C-C) = 0.007 Å
• R factor = 0.020
• wR factor = 0.047
• Data-to-parameter ratio = 19.8

checkCIF/PLATON results

No syntax errors found



Alert level C
PLAT241_ALERT_2_C Check High   U(eq) as Compared to Neighbors ....         C6
PLAT242_ALERT_2_C Check Low    U(eq) as Compared to Neighbors ....         W1

   0 ALERT level A = In general: serious problem
   0 ALERT level B = Potentially serious problem
   2 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
   0 ALERT type 3 Indicator that the structure quality may be low
   0 ALERT type 4 Improvement, methodology, query or suggestion

---

Computing details

Data collection: SMART-NT (Bruker, 1998); cell refinement: SAINT-Plus (Bruker, 1999); data reduction: XPREP (Bruker, 1999); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997); software used to prepare material for publication: WinGX (Farrugia, 1999) and PLATON (Spek, 2003).

Tricarbonyliodo(η⁵-methylcyclopentadienyl)tungsten

Crystal data

[W(C6H8)I(CO)3]	F(000) = 848
Mr = 473.9	Dx = 2.8 Mg m^−3
Monoclinic, C2/m	Melting point: 456 K
Hall symbol: -C 2y	Mo Kα radiation, λ = 0.71073 Å
a = 13.5020 (16) Å	Cell parameters from 939 reflections
b = 8.4577 (10) Å	θ = 2.9–28.3°
c = 10.1886 (12) Å	µ = 13.00 mm^−1
β = 104.949 (2)°	T = 293 K
V = 1124.1 (2) Å^3	Needle, orange
Z = 4	0.35 × 0.12 × 0.1 mm

Data collection

Bruker SMART CCD area-detector diffractometer	1485 independent reflections
Radiation source: fine-focus sealed tube	1363 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.022
φ and ω scans	θmax = 28.3°, θmin = 2.1°
Absorption correction: multi-scan (SADABS; Bruker, 1999)	h = −12→17
Tmin = 0.165, Tmax = 0.273	k = −11→11
3934 measured reflections	l = −13→11

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)] = 0.02	H-atom parameters constrained
wR(F^2) = 0.047	w = 1/[σ^2(Fo^2) + (0.021P)^2 + 2.5564P] where P = (Fo^2 + 2Fc^2)/3
S = 1.06	(Δ/σ)max = 0.001
1485 reflections	Δρmax = 0.80 e Å^−3
75 parameters	Δρmin = −0.57 e Å^−3
0 restraints	Extinction correction: SHELXL97, Fc^*=kFc[1+0.001xFc^2λ^3/sin(2θ)]^-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.00169 (9)

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	Occ. (<1)
W1	0.725916 (15)	0.5	0.70453 (2)	0.03813 (9)
I2	0.58022 (3)	0.5	0.86264 (4)	0.05197 (12)
O2	0.5990 (3)	0.8093 (5)	0.6123 (4)	0.0768 (10)
C2	0.6428 (3)	0.6946 (6)	0.6453 (4)	0.0511 (10)
O1	0.6946 (4)	0.5	0.3901 (5)	0.0844 (18)
C1	0.7069 (5)	0.5	0.5048 (6)	0.0553 (15)
C4	0.8538 (4)	0.5	0.9206 (6)	0.0490 (14)
C5	0.8657 (3)	0.6344 (6)	0.8460 (5)	0.0558 (11)
H5	0.859	0.7389	0.8708	0.067*
C6	0.8898 (3)	0.5821 (7)	0.7259 (5)	0.0670 (14)
H6	0.9033	0.6465	0.6587	0.08*
C9	0.8400 (6)	0.5	1.0624 (7)	0.077 (2)
H9A	0.822	0.3956	1.0851	0.116*	0.5
H9B	0.7865	0.5725	1.0675	0.116*	0.5
H9C	0.9029	0.5319	1.1252	0.116*	0.5

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
W1	0.02792 (12)	0.04960 (15)	0.03782 (13)	0	0.01023 (8)	0
I2	0.0416 (2)	0.0648 (3)	0.0566 (2)	0	0.02549 (17)	0
O2	0.074 (2)	0.074 (3)	0.084 (2)	0.027 (2)	0.0247 (19)	0.025 (2)
C2	0.042 (2)	0.066 (3)	0.049 (2)	0.005 (2)	0.0159 (17)	0.010 (2)
O1	0.072 (3)	0.139 (6)	0.043 (3)	0	0.016 (2)	0
C1	0.040 (3)	0.076 (5)	0.051 (3)	0	0.014 (3)	0
C4	0.031 (3)	0.067 (4)	0.046 (3)	0	0.005 (2)	0
C5	0.041 (2)	0.056 (3)	0.063 (3)	−0.0109 (19)	0.0012 (18)	−0.002 (2)
C6	0.0315 (19)	0.111 (4)	0.057 (2)	−0.015 (2)	0.0101 (17)	0.015 (3)
C9	0.057 (4)	0.126 (7)	0.043 (3)	0	0.005 (3)	0

Geometric parameters (Å, º)

W1—C1	1.984 (6)	C4—C5^i	1.399 (6)
W1—C2^i	1.996 (5)	C4—C5	1.399 (6)
W1—C2	1.996 (5)	C4—C9	1.504 (9)
W1—C6	2.275 (4)	C5—C6	1.416 (7)
W1—C6^i	2.275 (4)	C5—H5	0.93
W1—C5	2.351 (4)	C6—C6^i	1.388 (12)
W1—C5^i	2.351 (4)	C6—H6	0.93
W1—C4	2.422 (5)	C9—H9A	0.96
W1—I2	2.8460 (5)	C9—H9B	0.96
O2—C2	1.140 (5)	C9—H9C	0.96
O1—C1	1.138 (7)
C1—W1—C2^i	77.05 (15)	C6—W1—I2	137.98 (12)
C1—W1—C2	77.05 (15)	C6^i—W1—I2	137.98 (12)
C2^i—W1—C2	111.1 (3)	C5—W1—I2	102.44 (12)
C1—W1—C6	87.9 (2)	C5^i—W1—I2	102.44 (12)
C2^i—W1—C6	137.5 (2)	C4—W1—I2	85.43 (14)
C2—W1—C6	103.58 (19)	O2—C2—W1	177.1 (4)
C1—W1—C6^i	87.9 (2)	O1—C1—W1	179.0 (6)
C2^i—W1—C6^i	103.58 (19)	C5^i—C4—C5	108.7 (6)
C2—W1—C6^i	137.5 (2)	C5^i—C4—C9	125.6 (3)
C6—W1—C6^i	35.5 (3)	C5—C4—C9	125.6 (3)
C1—W1—C5	119.98 (19)	C5^i—C4—W1	70.2 (3)
C2^i—W1—C5	152.14 (18)	C5—C4—W1	70.2 (3)
C2—W1—C5	94.97 (18)	C9—C4—W1	129.6 (4)
C6—W1—C5	35.60 (17)	C4—C5—C6	107.4 (5)
C6^i—W1—C5	58.80 (18)	C4—C5—W1	75.7 (3)
C1—W1—C5^i	119.98 (19)	C6—C5—W1	69.3 (2)
C2^i—W1—C5^i	94.97 (17)	C4—C5—H5	126.3
C2—W1—C5^i	152.14 (18)	C6—C5—H5	126.3
C6—W1—C5^i	58.80 (18)	W1—C5—H5	120.5
C6^i—W1—C5^i	35.60 (17)	C6^i—C6—C5	108.2 (3)
C5—W1—C5^i	57.8 (2)	C6^i—C6—W1	72.24 (15)
C1—W1—C4	143.6 (2)	C5—C6—W1	75.1 (2)
C2^i—W1—C4	119.24 (14)	C6^i—C6—H6	125.9
C2—W1—C4	119.24 (14)	C5—C6—H6	125.9
C6—W1—C4	57.67 (17)	W1—C6—H6	118.6
C6^i—W1—C4	57.67 (17)	C4—C9—H9A	109.5
C5—W1—C4	34.06 (13)	C4—C9—H9B	109.5
C5^i—W1—C4	34.06 (13)	H9A—C9—H9B	109.5
C1—W1—I2	130.93 (18)	C4—C9—H9C	109.5
C2^i—W1—I2	75.77 (12)	H9A—C9—H9C	109.5
C2—W1—I2	75.77 (12)	H9B—C9—H9C	109.5
C1—W1—C4—C5^i	−59.7 (3)	C2—W1—C5—C4	138.3 (3)
C2^i—W1—C4—C5^i	49.4 (4)	C6—W1—C5—C4	−115.2 (4)
C2—W1—C4—C5^i	−168.8 (3)	C6^i—W1—C5—C4	−77.3 (3)
C6—W1—C4—C5^i	−80.9 (4)	C5^i—W1—C5—C4	−35.2 (3)
C6^i—W1—C4—C5^i	−38.6 (3)	I2—W1—C5—C4	61.8 (3)
C5—W1—C4—C5^i	−119.4 (6)	C1—W1—C5—C6	−28.5 (4)
I2—W1—C4—C5^i	120.3 (3)	C2^i—W1—C5—C6	94.0 (4)
C1—W1—C4—C5	59.7 (3)	C2—W1—C5—C6	−106.5 (3)
C2^i—W1—C4—C5	168.8 (3)	C6^i—W1—C5—C6	38.0 (4)
C2—W1—C4—C5	−49.4 (4)	C5^i—W1—C5—C6	80.0 (3)
C6—W1—C4—C5	38.6 (3)	C4—W1—C5—C6	115.2 (4)
C6^i—W1—C4—C5	80.9 (4)	I2—W1—C5—C6	177.0 (3)
C5^i—W1—C4—C5	119.4 (6)	C4—C5—C6—C6^i	1.6 (4)
I2—W1—C4—C5	−120.3 (3)	W1—C5—C6—C6^i	−65.2 (2)
C1—W1—C4—C9	180.000 (2)	C4—C5—C6—W1	66.8 (3)
C2^i—W1—C4—C9	−70.89 (15)	C1—W1—C6—C6^i	−89.3 (2)
C2—W1—C4—C9	70.89 (15)	C2^i—W1—C6—C6^i	−21.2 (2)
C6—W1—C4—C9	158.84 (18)	C2—W1—C6—C6^i	−165.5 (2)
C6^i—W1—C4—C9	−158.84 (18)	C5—W1—C6—C6^i	115.1 (3)
C5—W1—C4—C9	120.3 (3)	C5^i—W1—C6—C6^i	38.03 (17)
C5^i—W1—C4—C9	−120.3 (3)	C4—W1—C6—C6^i	78.3 (2)
I2—W1—C4—C9	0.000 (2)	I2—W1—C6—C6^i	110.82 (17)
C5^i—C4—C5—C6	−2.6 (6)	C1—W1—C6—C5	155.5 (3)
C9—C4—C5—C6	172.4 (5)	C2^i—W1—C6—C5	−136.3 (3)
W1—C4—C5—C6	−62.5 (3)	C2—W1—C6—C5	79.4 (3)
C5^i—C4—C5—W1	59.9 (4)	C6^i—W1—C6—C5	−115.1 (3)
C9—C4—C5—W1	−125.1 (6)	C5^i—W1—C6—C5	−77.1 (4)
C1—W1—C5—C4	−143.8 (3)	C4—W1—C6—C5	−36.8 (2)
C2^i—W1—C5—C4	−21.2 (5)	I2—W1—C6—C5	−4.3 (4)

Symmetry code: (i) x, −y+1, z.