Dicarbon­yl(η5-1-carboxy­cyclo­penta­dien­yl)methyl­iron(II)

Bala, M.D.; Munyaneza, A.; Coville, N.J.

doi:10.1107/S1600536805030473

Dicarbonyl(η⁵-1-carboxycyclopentadienyl)methyliron(II)

M. D. Bala, A. Munyaneza and N. J. Coville

The title carboxyl-functionalized iron complex, [Fe(CH₃)(C₆H₅O₂)(CO)₂], was prepared by the reaction of CO₂ with a lithiated parent unsubstituted compound. The Fe(CO)₂Me legs of the tripodal piano stool are characterized by disorder between the methyl group and the carbonyl group, and the two ligands were refined (50% site occupancy) over the two positions. The ligands are alternately located on either side of a local pseudo-mirror plane running through the carboxylic functionality and the central Fe atom.

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Supporting information

	Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536805030473/lh6507sup1.cif Contains datablocks global, I
	Structure factor file (CIF format) https://doi.org/10.1107/S1600536805030473/lh6507Isup2.hkl Contains datablock I

CCDC reference: 287639

checkCIF report

Key indicators

Single-crystal X-ray study
T = 173 K
Mean (C-C) = 0.002 Å
Disorder in main residue
R factor = 0.025
wR factor = 0.069
Data-to-parameter ratio = 14.6

checkCIF/PLATON results

No syntax errors found



Alert level C
PLAT062_ALERT_4_C Rescale T(min) & T(max) by .....................       0.98
PLAT301_ALERT_3_C Main Residue  Disorder .........................      18.00 Perc.
PLAT720_ALERT_4_C Number of Unusual/Non-Standard Label(s) ........          3

   0 ALERT level A = In general: serious problem
   0 ALERT level B = Potentially serious problem
   3 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
   0 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

Comment top

Group six analogs of the title complex have been prepared (El Mouattasim et al., 1994) with the aim of utilizing the functional carboxylic acid group as labeling agents for amino acids. We prepared the title compound, (I), as part of our interest in solvent-free solid–gas reactions. It was envisaged that the network of hydrogen bonding between neighbouring molecules via the carboxylic acid functionality will serve as channels for small gaseous molecules to permeate into the crystal lattice (Braga et al., 2002; Fig. 2). Preliminary studies with SO₂ have indicated otherwise, indicating that intramolecular forces, such as steric interactions between ligands bonded to the central metal atom may be more crucial in influencing the single-crystal/gas reactivity (Munyaneza et al., 2005).

In the title compound, the Fe(CO)₂Me leg of the tripodal piano stool is characterized by a disordered Me group which was refined over positions C2 and C2'. These are located on opposite sides of a local psuedo-mirror plane running through the carboxylic acid functionality and the central Fe metal with 50% occupancy of each site (Fig. 1). Mousser et al. (1996) have prepared four-legged piano stool tungsten analogs of the title complex, and it is interesting to note that the Me group was similarly disordered between two trans positions in syn and anti configurations relative to the carboxylic acid functional group. In the crystal structure, molecules form the expected centrosymmetric dimers via O—H···O hydrogen bonds (Table 1 and Fig. 2).

Experimental top

The title complex was prepared by adapting the method of El Mouattasim et al. (1994) except that (η⁵-C₅H₅)Fe(CO)₂Me and butyllithium were substituted for (η⁵-C₅H₅)Mo(CO)₃Me and sec-butyllithium. Single crystals suitable for X-ray diffraction were grown from CH₂Cl₂/hexane. IR v_CO (CH₂Cl₂, cm⁻¹): 2059 (vs), 1998 (vs); ¹H NMR (CDCl₃, p.p.m.): 5.31 (s, 2H, CpH), 4.86 (s, 2H, CpH), 0.28 (s, 3H, Me).

Computing details top

Data collection: SMART (Bruker, 1999); cell refinement: SAINT (Bruker, 1999); data reduction: SAINT; program(s) used to solve structure: SHELXTL (Bruker, 1999); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: SHELXTL and ORTEP-3 (Farrugia, 1999); software used to prepare material for publication: SHELXTL.

Figures top

	Fig. 1. ORTEP-3 (Farrugia, 1999) diagrams of the title complex, showing the two conformations with the Me and CO ligands interchanged. Displacement ellipsoids are shown at 50% probability level.
	Fig. 2. Packing diagram, showing the hydrogen bonding (dashed lines) between neighbouring carboxyl molecules.

Dicarbonyl(η⁵-1-carboxycyclopentadienyl)methyliron(II) top

Crystal data top

[Fe(CH₃)(C₆H₅O₂)(CO)₂]	F(000) = 480
M_r = 236.00	D_x = 1.657 Mg m⁻³
Monoclinic, P2₁/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 830 reflections
a = 7.6183 (15) Å	θ = 2.6–30.2°
b = 10.714 (2) Å	µ = 1.58 mm⁻¹
c = 12.039 (2) Å	T = 173 K
β = 105.661 (4)°	Block, brown
V = 946.2 (3) Å³	0.24 × 0.19 × 0.19 mm
Z = 4

Data collection top

Bruker SMART 1K CCD diffractometer	2276 independent reflections
Radiation source: fine-focus sealed tube	1978 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.024
ϕ and ω scans	θ_max = 28.0°, θ_min = 2.6°
Absorption correction: multi-scan (SADABS; Bruker, 1999)	h = −10→9
T_min = 0.704, T_max = 0.754	k = −13→14
6617 measured reflections	l = −11→15

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)] = 0.025	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.070	H-atom parameters constrained
S = 1.08	w = 1/[σ²(F_o²) + (0.0402P)² + 0.1317P] where P = (F_o² + 2F_c²)/3
2276 reflections	(Δ/σ)_max = 0.034
156 parameters	Δρ_max = 0.31 e Å⁻³
8 restraints	Δρ_min = −0.30 e Å⁻³

Crystal data top

[Fe(CH₃)(C₆H₅O₂)(CO)₂]	V = 946.2 (3) Å³
M_r = 236.00	Z = 4
Monoclinic, P2₁/c	Mo Kα radiation
a = 7.6183 (15) Å	µ = 1.58 mm⁻¹
b = 10.714 (2) Å	T = 173 K
c = 12.039 (2) Å	0.24 × 0.19 × 0.19 mm
β = 105.661 (4)°

Data collection top

Bruker SMART 1K CCD diffractometer	2276 independent reflections
Absorption correction: multi-scan (SADABS; Bruker, 1999)	1978 reflections with I > 2σ(I)
T_min = 0.704, T_max = 0.754	R_int = 0.024
6617 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.025	8 restraints
wR(F²) = 0.070	H-atom parameters constrained
S = 1.08	Δρ_max = 0.31 e Å⁻³
2276 reflections	Δρ_min = −0.30 e Å⁻³
156 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)
C2	0.556 (2)	0.2166 (12)	0.1394 (13)	0.039 (2)	0.551 (5)
H2A	0.6448	0.2205	0.0938	0.059*	0.551 (5)
H2B	0.5549	0.2964	0.1790	0.059*	0.551 (5)
H2C	0.4347	0.1998	0.0884	0.059*	0.551 (5)
C1	0.4782 (19)	−0.0213 (14)	0.1556 (13)	0.0298 (17)	0.551 (5)
O3	0.3807 (4)	−0.0845 (2)	0.0875 (2)	0.0456 (9)	0.551 (5)
C1'	0.580 (3)	0.2079 (15)	0.1612 (15)	0.035 (2)	0.449 (5)
O3'	0.5522 (5)	0.2868 (3)	0.0945 (3)	0.0536 (12)	0.449 (5)
C2'	0.473 (3)	−0.0340 (19)	0.1368 (17)	0.035 (3)	0.449 (5)
H2'1	0.5479	−0.0696	0.0900	0.052*	0.449 (5)
H2'2	0.3730	0.0144	0.0872	0.052*	0.449 (5)
H2'3	0.4229	−0.1015	0.1738	0.052*	0.449 (5)
C3	0.4404 (2)	0.11550 (19)	0.31256 (15)	0.0366 (4)
C4	0.89004 (19)	0.03310 (16)	0.25142 (12)	0.0247 (3)
C5	0.8231 (2)	−0.06350 (14)	0.31040 (14)	0.0271 (3)
H5	0.8071	−0.1485	0.2876	0.033*
C6	0.7851 (2)	−0.01092 (17)	0.40820 (13)	0.0313 (4)
H6	0.7373	−0.0542	0.4625	0.038*
C7	0.8300 (2)	0.11786 (18)	0.41208 (14)	0.0335 (4)
H7	0.8179	0.1755	0.4695	0.040*
C8	0.8956 (2)	0.14543 (16)	0.31631 (14)	0.0319 (4)
H8	0.9363	0.2247	0.2980	0.038*
C9	0.9399 (2)	0.01941 (15)	0.14299 (13)	0.0244 (3)
O1	0.99336 (18)	0.11962 (11)	0.10201 (11)	0.0339 (3)
H1	1.0160	0.1032	0.0391	0.051*
O2	0.93037 (18)	−0.08486 (10)	0.09565 (11)	0.0329 (3)
O5	0.3221 (2)	0.13996 (19)	0.34747 (14)	0.0649 (5)
Fe	0.62709 (3)	0.07778 (2)	0.257978 (18)	0.02464 (9)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
C2	0.051 (5)	0.039 (4)	0.030 (5)	0.003 (3)	0.014 (4)	0.001 (2)
C1	0.028 (3)	0.036 (3)	0.024 (4)	0.003 (2)	0.003 (2)	−0.001 (2)
O3	0.0418 (16)	0.0463 (16)	0.0384 (15)	−0.0099 (11)	−0.0066 (12)	−0.0078 (11)
C1'	0.039 (4)	0.042 (4)	0.027 (5)	0.014 (3)	0.016 (4)	0.006 (3)
O3'	0.076 (3)	0.048 (2)	0.042 (2)	0.0259 (18)	0.0256 (17)	0.0233 (16)
C2'	0.037 (4)	0.041 (5)	0.024 (5)	−0.008 (3)	0.003 (3)	−0.004 (3)
C3	0.0292 (8)	0.0505 (11)	0.0298 (8)	0.0045 (8)	0.0073 (7)	0.0034 (8)
C4	0.0214 (7)	0.0279 (8)	0.0255 (7)	0.0001 (6)	0.0076 (6)	−0.0002 (6)
C5	0.0265 (8)	0.0267 (8)	0.0278 (8)	0.0030 (6)	0.0067 (6)	0.0040 (6)
C6	0.0271 (8)	0.0438 (10)	0.0224 (8)	0.0030 (7)	0.0058 (6)	0.0066 (7)
C7	0.0280 (8)	0.0457 (10)	0.0267 (8)	−0.0036 (7)	0.0072 (6)	−0.0103 (7)
C8	0.0293 (8)	0.0326 (9)	0.0365 (9)	−0.0078 (7)	0.0132 (7)	−0.0084 (7)
C9	0.0204 (7)	0.0263 (8)	0.0273 (7)	0.0023 (6)	0.0081 (6)	0.0020 (6)
O1	0.0452 (7)	0.0276 (6)	0.0358 (6)	−0.0043 (5)	0.0227 (5)	−0.0004 (5)
O2	0.0459 (7)	0.0241 (6)	0.0342 (6)	0.0045 (5)	0.0200 (6)	0.0004 (5)
O5	0.0393 (8)	0.1098 (15)	0.0507 (9)	0.0129 (9)	0.0209 (7)	0.0090 (9)
Fe	0.02289 (13)	0.03106 (14)	0.02088 (13)	0.00366 (8)	0.00746 (9)	0.00159 (8)

Geometric parameters (Å, º) top

C2—Fe	2.031 (8)	C4—C9	1.462 (2)
C2—H2A	0.9800	C4—Fe	2.0818 (15)
C2—H2B	0.9800	C5—C6	1.404 (2)
C2—H2C	0.9800	C5—Fe	2.1002 (16)
C1—O3	1.164 (7)	C5—H5	0.9500
C1—Fe	1.782 (7)	C6—C7	1.419 (3)
C1'—O3'	1.146 (7)	C6—Fe	2.1088 (16)
C1'—Fe	1.790 (8)	C6—H6	0.9500
C2'—Fe	2.004 (9)	C7—C8	1.406 (2)
C2'—H2'1	0.9800	C7—Fe	2.1138 (17)
C2'—H2'2	0.9800	C7—H7	0.9500
C2'—H2'3	0.9800	C8—Fe	2.1040 (16)
C3—O5	1.124 (2)	C8—H8	0.9500
C3—Fe	1.7670 (19)	C9—O2	1.2472 (19)
C4—C5	1.425 (2)	C9—O1	1.2926 (19)
C4—C8	1.429 (2)	O1—H1	0.8400

Fe—C2—H2A	109.5	O1—C9—C4	116.23 (14)
Fe—C2—H2B	109.5	C9—O1—H1	109.5
H2A—C2—H2B	109.5	C3—Fe—C1	88.1 (6)
Fe—C2—H2C	109.5	C3—Fe—C1'	91.4 (6)
H2A—C2—H2C	109.5	C1—Fe—C1'	92.1 (9)
H2B—C2—H2C	109.5	C3—Fe—C2'	92.0 (7)
O3—C1—Fe	178.9 (16)	C1—Fe—C2'	4.0 (13)
O3'—C1'—Fe	176.1 (18)	C1'—Fe—C2'	91.0 (10)
Fe—C2'—H2'1	109.5	C3—Fe—C2	90.3 (5)
Fe—C2'—H2'2	109.5	C1—Fe—C2	87.2 (8)
H2'1—C2'—H2'2	109.5	C1'—Fe—C2	4.9 (12)
Fe—C2'—H2'3	109.5	C2'—Fe—C2	86.2 (9)
H2'1—C2'—H2'3	109.5	C3—Fe—C4	161.09 (7)
H2'2—C2'—H2'3	109.5	C1—Fe—C4	106.0 (5)
O5—C3—Fe	179.7 (2)	C1'—Fe—C4	100.3 (6)
C5—C4—C8	107.52 (14)	C2'—Fe—C4	102.4 (7)
C5—C4—C9	125.88 (15)	C2—Fe—C4	102.6 (5)
C8—C4—C9	126.59 (15)	C3—Fe—C5	129.16 (8)
C5—C4—Fe	70.77 (9)	C1—Fe—C5	92.7 (5)
C8—C4—Fe	70.87 (9)	C1'—Fe—C5	139.2 (6)
C9—C4—Fe	122.78 (10)	C2'—Fe—C5	91.0 (7)
C6—C5—C4	108.00 (14)	C2—Fe—C5	140.5 (5)
C6—C5—Fe	70.84 (9)	C4—Fe—C5	39.84 (6)
C4—C5—Fe	69.38 (9)	C3—Fe—C8	127.20 (8)
C6—C5—H5	126.0	C1—Fe—C8	144.7 (6)
C4—C5—H5	126.0	C1'—Fe—C8	87.4 (7)
Fe—C5—H5	125.4	C2'—Fe—C8	140.7 (7)
C5—C6—C7	108.36 (14)	C2—Fe—C8	91.9 (5)
C5—C6—Fe	70.18 (9)	C4—Fe—C8	39.93 (6)
C7—C6—Fe	70.55 (9)	C5—Fe—C8	66.40 (6)
C5—C6—H6	125.8	C3—Fe—C6	96.57 (7)
C7—C6—H6	125.8	C1—Fe—C6	115.7 (6)
Fe—C6—H6	125.0	C1'—Fe—C6	151.2 (7)
C8—C7—C6	108.26 (15)	C2'—Fe—C6	116.2 (7)
C8—C7—Fe	70.15 (9)	C2—Fe—C6	156.2 (5)
C6—C7—Fe	70.17 (9)	C4—Fe—C6	66.21 (6)
C8—C7—H7	125.9	C5—Fe—C6	38.98 (6)
C6—C7—H7	125.9	C8—Fe—C6	65.84 (7)
Fe—C7—H7	125.4	C3—Fe—C7	95.66 (8)
C7—C8—C4	107.86 (15)	C1—Fe—C7	154.9 (6)
C7—C8—Fe	70.90 (9)	C1'—Fe—C7	112.5 (7)
C4—C8—Fe	69.20 (8)	C2'—Fe—C7	155.0 (7)
C7—C8—H8	126.1	C2—Fe—C7	117.4 (5)
C4—C8—H8	126.1	C4—Fe—C7	66.21 (6)
Fe—C8—H8	125.4	C5—Fe—C7	65.82 (7)
O2—C9—O1	123.71 (15)	C8—Fe—C7	38.95 (6)
O2—C9—C4	120.06 (14)	C6—Fe—C7	39.28 (7)

C8—C4—C5—C6	1.11 (18)	C4—C5—Fe—C2'	108.4 (7)
C9—C4—C5—C6	−177.69 (14)	C6—C5—Fe—C2	141.9 (8)
Fe—C4—C5—C6	−60.60 (11)	C4—C5—Fe—C2	23.2 (8)
C8—C4—C5—Fe	61.71 (11)	C6—C5—Fe—C4	118.70 (14)
C9—C4—C5—Fe	−117.09 (15)	C6—C5—Fe—C8	80.21 (10)
C4—C5—C6—C7	−0.82 (18)	C4—C5—Fe—C8	−38.50 (9)
Fe—C5—C6—C7	−60.49 (11)	C4—C5—Fe—C6	−118.70 (14)
C4—C5—C6—Fe	59.68 (11)	C6—C5—Fe—C7	37.44 (10)
C5—C6—C7—C8	0.20 (18)	C4—C5—Fe—C7	−81.26 (10)
Fe—C6—C7—C8	−60.06 (12)	C7—C8—Fe—C3	42.07 (15)
C5—C6—C7—Fe	60.26 (11)	C4—C8—Fe—C3	160.67 (11)
C6—C7—C8—C4	0.49 (19)	C7—C8—Fe—C1	−138.3 (10)
Fe—C7—C8—C4	−59.58 (11)	C4—C8—Fe—C1	−19.7 (10)
C6—C7—C8—Fe	60.07 (11)	C7—C8—Fe—C1'	131.9 (7)
C5—C4—C8—C7	−0.99 (18)	C4—C8—Fe—C1'	−109.5 (7)
C9—C4—C8—C7	177.80 (14)	C7—C8—Fe—C2'	−139.9 (11)
Fe—C4—C8—C7	60.66 (12)	C4—C8—Fe—C2'	−21.3 (11)
C5—C4—C8—Fe	−61.65 (11)	C7—C8—Fe—C2	133.9 (5)
C9—C4—C8—Fe	117.15 (15)	C4—C8—Fe—C2	−107.5 (5)
C5—C4—C9—O2	−2.1 (2)	C7—C8—Fe—C4	−118.60 (15)
C8—C4—C9—O2	179.28 (15)	C7—C8—Fe—C5	−80.18 (11)
Fe—C4—C9—O2	−91.13 (17)	C4—C8—Fe—C5	38.42 (9)
C5—C4—C9—O1	178.23 (15)	C7—C8—Fe—C6	−37.38 (11)
C8—C4—C9—O1	−0.3 (2)	C4—C8—Fe—C6	81.21 (11)
Fe—C4—C9—O1	89.24 (16)	C4—C8—Fe—C7	118.60 (15)
C5—C4—Fe—C3	62.8 (3)	C5—C6—Fe—C3	150.25 (11)
C8—C4—Fe—C3	−54.5 (3)	C7—C6—Fe—C3	−90.91 (11)
C9—C4—Fe—C3	−176.3 (2)	C5—C6—Fe—C1	59.2 (6)
C5—C4—Fe—C1	−74.4 (6)	C7—C6—Fe—C1	178.0 (6)
C8—C4—Fe—C1	168.3 (6)	C5—C6—Fe—C1'	−104.5 (14)
C9—C4—Fe—C1	46.5 (7)	C7—C6—Fe—C1'	14.3 (14)
C5—C4—Fe—C1'	−169.6 (7)	C5—C6—Fe—C2'	54.7 (8)
C8—C4—Fe—C1'	73.1 (7)	C7—C6—Fe—C2'	173.5 (8)
C9—C4—Fe—C1'	−48.7 (7)	C5—C6—Fe—C2	−103.8 (13)
C5—C4—Fe—C2'	−76.3 (7)	C7—C6—Fe—C2	15.1 (13)
C8—C4—Fe—C2'	166.4 (7)	C5—C6—Fe—C4	−37.89 (9)
C9—C4—Fe—C2'	44.6 (8)	C7—C6—Fe—C4	80.95 (10)
C5—C4—Fe—C2	−165.1 (5)	C7—C6—Fe—C5	118.83 (14)
C8—C4—Fe—C2	77.6 (5)	C5—C6—Fe—C8	−81.77 (10)
C9—C4—Fe—C2	−44.2 (5)	C7—C6—Fe—C8	37.07 (9)
C8—C4—Fe—C5	−117.28 (13)	C5—C6—Fe—C7	−118.83 (14)
C9—C4—Fe—C5	120.91 (18)	C8—C7—Fe—C3	−147.57 (12)
C5—C4—Fe—C8	117.28 (13)	C6—C7—Fe—C3	93.47 (11)
C9—C4—Fe—C8	−121.81 (18)	C8—C7—Fe—C1	114.7 (14)
C5—C4—Fe—C6	37.08 (10)	C6—C7—Fe—C1	−4.2 (14)
C8—C4—Fe—C6	−80.20 (11)	C8—C7—Fe—C1'	−53.6 (7)
C9—C4—Fe—C6	157.99 (16)	C6—C7—Fe—C1'	−172.6 (7)
C5—C4—Fe—C7	80.19 (10)	C8—C7—Fe—C2'	105.2 (16)
C8—C4—Fe—C7	−37.09 (10)	C6—C7—Fe—C2'	−13.8 (16)
C9—C4—Fe—C7	−158.91 (16)	C8—C7—Fe—C2	−54.2 (6)
C6—C5—Fe—C3	−39.47 (14)	C6—C7—Fe—C2	−173.2 (6)
C4—C5—Fe—C3	−158.18 (11)	C8—C7—Fe—C4	38.01 (10)
C6—C5—Fe—C1	−129.2 (6)	C6—C7—Fe—C4	−80.95 (10)
C4—C5—Fe—C1	112.1 (6)	C8—C7—Fe—C5	81.80 (11)
C6—C5—Fe—C1'	134.5 (11)	C6—C7—Fe—C5	−37.16 (9)
C4—C5—Fe—C1'	15.8 (11)	C6—C7—Fe—C8	−118.96 (15)
C6—C5—Fe—C2'	−132.9 (7)	C8—C7—Fe—C6	118.96 (15)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1···O2ⁱ	0.84	1.79	2.6240 (19)	174

Symmetry code: (i) −x+2, −y, −z.

Experimental details

Crystal data
Chemical formula	[Fe(CH₃)(C₆H₅O₂)(CO)₂]
M_r	236.00
Crystal system, space group	Monoclinic, P2₁/c
Temperature (K)	173
a, b, c (Å)	7.6183 (15), 10.714 (2), 12.039 (2)
β (°)	105.661 (4)
V (Å³)	946.2 (3)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	1.58
Crystal size (mm)	0.24 × 0.19 × 0.19

Data collection
Diffractometer	Bruker SMART 1K CCD diffractometer
Absorption correction	Multi-scan (SADABS; Bruker, 1999)
T_min, T_max	0.704, 0.754
No. of measured, independent and observed [I > 2σ(I)] reflections	6617, 2276, 1978
R_int	0.024
(sin θ/λ)_max (Å⁻¹)	0.661

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.025, 0.070, 1.08
No. of reflections	2276
No. of parameters	156
No. of restraints	8
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.31, −0.30

Computer programs: SMART (Bruker, 1999), SAINT (Bruker, 1999), SAINT, SHELXTL (Bruker, 1999), SHELXL97 (Sheldrick, 1997), SHELXTL and ORTEP-3 (Farrugia, 1999), SHELXTL.

Selected geometric parameters (Å, º) top

C2—Fe	2.031 (8)	C2'—Fe	2.004 (9)
C1—O3	1.164 (7)	C3—O5	1.124 (2)
C1—Fe	1.782 (7)	C3—Fe	1.7670 (19)
C1'—O3'	1.146 (7)	C9—O2	1.2472 (19)
C1'—Fe	1.790 (8)	C9—O1	1.2926 (19)

O3—C1—Fe	178.9 (16)	C3—Fe—C1	88.1 (6)
O3'—C1'—Fe	176.1 (18)	C3—Fe—C2	90.3 (5)
O5—C3—Fe	179.7 (2)	C1—Fe—C2	87.2 (8)
O2—C9—O1	123.71 (15)