Di­carbonyl­(η5-cyclo­penta­dienyl)­iodo­iron(II)

Zeller, M.; Lazich, E.; Hunter, A.D.

doi:10.1107/S1600536803019950

Dicarbonyl(η⁵-cyclopentadienyl)iodoiron(II)

In the title compound, [Fe(C₅H₅)I(CO)₂], there are two independent molecules in the asymmetric unit. They exhibit a three-legged-piano-stool geometry.

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Supporting information

	Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536803019950/ob6294sup1.cif Contains datablocks global, I
	Structure factor file (CIF format) https://doi.org/10.1107/S1600536803019950/ob6294Isup2.hkl Contains datablock I

CCDC reference: 225675

checkCIF report

Key indicators

Single-crystal X-ray study
T = 100 K
Mean (C-C) = 0.005 Å
R factor = 0.026
wR factor = 0.059
Data-to-parameter ratio = 18.4

checkCIF/PLATON results

No syntax errors found



Alert level C
PLAT125_ALERT_4_C No _symmetry_space_group_name_Hall Given .......          ?
PLAT164_ALERT_4_C Nr. of Refined C-H H-Atoms in Heavy-At Struct...         10
PLAT232_ALERT_2_C Hirshfeld Test Diff (M-X)  Fe1    -   C1       =       7.77 su
PLAT232_ALERT_2_C Hirshfeld Test Diff (M-X)  Fe1    -   C2       =       8.74 su
PLAT232_ALERT_2_C Hirshfeld Test Diff (M-X)  Fe2    -   C3       =       5.42 su
PLAT232_ALERT_2_C Hirshfeld Test Diff (M-X)  Fe2    -   C4       =       5.94 su

   0 ALERT level A = In general: serious problem
   0 ALERT level B = Potentially serious problem
   6 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
   4 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
   2 ALERT type 4 Improvement, methodology, query or suggestion

Computing details top

Data collection: SMART (Bruker, 1997-2000); cell refinement: SAINT-Plus (Bruker, 1997-1999); data reduction: SAINT-Plus; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: SHELXL97.

eta5-cyclopentadienyldicarbonyliodoiron top

Crystal data top

[Fe(C₅H₅)(CO)₂I]	F(000) = 1136
M_r = 303.86	D_x = 2.374 Mg m⁻³
Monoclinic, P2₁/c	Mo Kα radiation, λ = 0.71073 Å
a = 13.1442 (7) Å	Cell parameters from 6438 reflections
b = 10.2568 (6) Å	θ = 2.5–28.3°
c = 12.8680 (7) Å	µ = 5.35 mm⁻¹
β = 101.502 (1)°	T = 100 K
V = 1699.99 (16) Å³	Block, red
Z = 8	0.22 × 0.17 × 0.17 mm

Data collection top

Bruker AXS SMART APEX CCD diffractometer	4207 independent reflections
Radiation source: fine-focus sealed tube	4077 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.025
ω scans	θ_max = 28.3°, θ_min = 1.6°
Absorption correction: multi-scan SADABS in SAINT-Plus (Bruker, 1997-1999)	h = −17→17
T_min = 0.295, T_max = 0.400	k = −13→13
17192 measured reflections	l = −17→17

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)] = 0.026	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.059	Only H-atom coordinates refined
S = 1.32	w = 1/[σ²(F_o²) + (0.0698P)² + 0.6662P] where P = (F_o² + 2F_c²)/3
4207 reflections	(Δ/σ)_max = 0.001
229 parameters	Δρ_max = 0.66 e Å⁻³
0 restraints	Δρ_min = −0.69 e Å⁻³

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
C3	0.1225 (2)	0.6623 (3)	0.2019 (2)	0.0188 (5)
I2	−0.094569 (13)	0.808051 (18)	0.159742 (14)	0.02053 (6)
I1	0.403466 (13)	0.728593 (18)	0.660422 (14)	0.02062 (6)
Fe1	0.59128 (3)	0.71181 (4)	0.77286 (3)	0.01426 (8)
Fe2	0.09140 (3)	0.79639 (4)	0.27729 (3)	0.01455 (8)
O4	0.16071 (16)	0.9916 (2)	0.14107 (16)	0.0258 (4)
O2	0.66637 (15)	0.9193 (2)	0.65208 (15)	0.0252 (4)
O3	0.14488 (16)	0.5759 (2)	0.15554 (15)	0.0252 (4)
O1	0.63702 (16)	0.5034 (2)	0.63439 (16)	0.0261 (4)
C1	0.6182 (2)	0.5845 (3)	0.6879 (2)	0.0192 (5)
C23	0.2050 (2)	0.8344 (3)	0.4111 (2)	0.0266 (6)
C4	0.1334 (2)	0.9153 (3)	0.1936 (2)	0.0185 (5)
C24	0.1688 (2)	0.7049 (3)	0.4163 (2)	0.0216 (6)
C2	0.6354 (2)	0.8374 (3)	0.6972 (2)	0.0189 (5)
C10	0.5610 (2)	0.6159 (3)	0.9076 (2)	0.0242 (6)
C21	0.0313 (3)	0.8428 (3)	0.4136 (2)	0.0277 (6)
C14	0.6682 (2)	0.6095 (3)	0.9050 (2)	0.0258 (6)
C11	0.5351 (3)	0.7500 (4)	0.9132 (2)	0.0321 (7)
C12	0.6246 (3)	0.8252 (3)	0.9125 (2)	0.0361 (8)
C20	0.0604 (2)	0.7095 (3)	0.4166 (2)	0.0230 (6)
C13	0.7068 (3)	0.7387 (4)	0.9064 (2)	0.0315 (7)
C22	0.1196 (3)	0.9198 (3)	0.4101 (2)	0.0307 (7)
H14	0.711 (3)	0.535 (4)	0.901 (3)	0.037*
H24	0.211 (3)	0.633 (4)	0.417 (3)	0.037*
H20	0.019 (3)	0.633 (4)	0.416 (3)	0.037*
H21	−0.033 (3)	0.872 (4)	0.411 (3)	0.037*
H10	0.521 (3)	0.542 (4)	0.906 (3)	0.037*
H13	0.775 (3)	0.762 (4)	0.905 (3)	0.037*
H22	0.119 (3)	1.008 (4)	0.410 (3)	0.037*
H11	0.464 (3)	0.782 (4)	0.915 (3)	0.037*
H12	0.623 (3)	0.921 (4)	0.911 (3)	0.037*
H23	0.267 (3)	0.862 (4)	0.410 (3)	0.037*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
C3	0.0161 (12)	0.0227 (13)	0.0174 (12)	−0.0013 (10)	0.0028 (10)	0.0011 (10)
I2	0.01349 (9)	0.02518 (10)	0.02109 (10)	0.00063 (6)	−0.00093 (7)	−0.00300 (6)
I1	0.01295 (9)	0.02599 (10)	0.02151 (10)	0.00000 (6)	0.00002 (7)	0.00033 (6)
Fe1	0.01325 (18)	0.01689 (17)	0.01249 (17)	−0.00003 (13)	0.00221 (14)	0.00027 (13)
Fe2	0.01330 (18)	0.01640 (17)	0.01338 (18)	−0.00014 (13)	0.00132 (14)	0.00011 (13)
O4	0.0261 (11)	0.0269 (11)	0.0246 (10)	−0.0033 (8)	0.0057 (8)	0.0056 (8)
O2	0.0260 (11)	0.0266 (10)	0.0223 (10)	−0.0062 (8)	0.0033 (8)	0.0034 (8)
O3	0.0303 (11)	0.0232 (10)	0.0232 (10)	0.0033 (8)	0.0081 (8)	−0.0023 (8)
O1	0.0322 (11)	0.0240 (10)	0.0236 (10)	0.0017 (9)	0.0094 (9)	−0.0037 (8)
C1	0.0169 (12)	0.0229 (13)	0.0181 (12)	−0.0008 (10)	0.0040 (10)	0.0040 (10)
C23	0.0250 (15)	0.0342 (16)	0.0170 (13)	−0.0116 (13)	−0.0042 (11)	0.0046 (12)
C4	0.0144 (12)	0.0209 (13)	0.0187 (12)	0.0013 (10)	0.0002 (10)	−0.0008 (10)
C24	0.0248 (14)	0.0215 (13)	0.0165 (12)	0.0066 (11)	−0.0007 (11)	0.0035 (10)
C2	0.0151 (12)	0.0255 (13)	0.0153 (12)	0.0004 (10)	0.0012 (10)	−0.0038 (10)
C10	0.0261 (14)	0.0297 (15)	0.0168 (13)	−0.0064 (12)	0.0046 (11)	0.0052 (11)
C21	0.0306 (16)	0.0393 (17)	0.0138 (12)	0.0137 (14)	0.0055 (11)	0.0001 (12)
C14	0.0295 (15)	0.0326 (16)	0.0136 (12)	0.0099 (13)	0.0000 (11)	0.0040 (11)
C11	0.0372 (18)	0.0460 (19)	0.0146 (13)	0.0183 (15)	0.0085 (13)	0.0040 (13)
C12	0.069 (3)	0.0230 (15)	0.0147 (14)	−0.0043 (15)	0.0039 (15)	−0.0045 (11)
C20	0.0251 (15)	0.0282 (15)	0.0159 (13)	−0.0049 (12)	0.0044 (11)	0.0013 (11)
C13	0.0251 (16)	0.050 (2)	0.0162 (13)	−0.0132 (14)	−0.0032 (12)	0.0033 (13)
C22	0.057 (2)	0.0169 (13)	0.0165 (13)	−0.0002 (13)	0.0020 (13)	−0.0017 (11)

Geometric parameters (Å, º) top

C3—O3	1.139 (3)	C23—C24	1.417 (4)
C3—Fe2	1.777 (3)	C23—C22	1.421 (5)
I2—Fe2	2.6082 (4)	C23—H23	0.87 (4)
I1—Fe1	2.6063 (4)	C24—C20	1.425 (4)
Fe1—C2	1.780 (3)	C24—H24	0.92 (4)
Fe1—C1	1.783 (3)	C10—C14	1.417 (4)
Fe1—C13	2.073 (3)	C10—C11	1.422 (5)
Fe1—C14	2.080 (3)	C10—H10	0.92 (4)
Fe1—C10	2.099 (3)	C21—C22	1.411 (5)
Fe1—C12	2.112 (3)	C21—C20	1.418 (4)
Fe1—C11	2.119 (3)	C21—H21	0.90 (4)
Fe2—C4	1.785 (3)	C14—C13	1.418 (5)
Fe2—C23	2.079 (3)	C14—H14	0.96 (4)
Fe2—C24	2.095 (3)	C11—C12	1.408 (5)
Fe2—C22	2.100 (3)	C11—H11	1.00 (4)
Fe2—C20	2.112 (3)	C12—C13	1.413 (5)
Fe2—C21	2.116 (3)	C12—H12	0.99 (4)
O4—C4	1.138 (3)	C20—H20	0.95 (4)
O2—C2	1.142 (3)	C13—H13	0.93 (4)
O1—C1	1.138 (3)	C22—H22	0.90 (4)

O3—C3—Fe2	178.1 (3)	C22—C23—Fe2	70.92 (17)
C2—Fe1—C1	93.95 (12)	C24—C23—H23	129 (3)
C2—Fe1—C13	95.29 (12)	C22—C23—H23	123 (3)
C1—Fe1—C13	113.82 (14)	Fe2—C23—H23	125 (2)
C2—Fe1—C14	130.82 (12)	O4—C4—Fe2	179.4 (3)
C1—Fe1—C14	90.48 (12)	C23—C24—C20	108.3 (3)
C13—Fe1—C14	39.93 (13)	C23—C24—Fe2	69.53 (16)
C2—Fe1—C10	157.94 (12)	C20—C24—Fe2	70.86 (16)
C1—Fe1—C10	104.86 (12)	C23—C24—H24	123 (2)
C13—Fe1—C10	66.78 (12)	C20—C24—H24	129 (2)
C14—Fe1—C10	39.63 (12)	Fe2—C24—H24	123 (2)
C2—Fe1—C12	91.82 (13)	O2—C2—Fe1	177.4 (2)
C1—Fe1—C12	153.15 (14)	C14—C10—C11	107.2 (3)
C13—Fe1—C12	39.44 (15)	C14—C10—Fe1	69.48 (16)
C14—Fe1—C12	66.28 (13)	C11—C10—Fe1	71.07 (17)
C10—Fe1—C12	66.21 (12)	C14—C10—H10	122 (2)
C2—Fe1—C11	122.62 (13)	C11—C10—H10	131 (2)
C1—Fe1—C11	143.42 (13)	Fe1—C10—H10	124 (2)
C13—Fe1—C11	65.87 (14)	C22—C21—C20	108.7 (3)
C14—Fe1—C11	65.91 (12)	C22—C21—Fe2	69.80 (17)
C10—Fe1—C11	39.41 (12)	C20—C21—Fe2	70.25 (16)
C12—Fe1—C11	38.88 (14)	C22—C21—H21	127 (2)
C2—Fe1—I1	91.41 (8)	C20—C21—H21	125 (2)
C1—Fe1—I1	89.41 (9)	Fe2—C21—H21	124 (2)
C13—Fe1—I1	155.22 (10)	C10—C14—C13	108.2 (3)
C14—Fe1—I1	137.65 (9)	C10—C14—Fe1	70.88 (16)
C10—Fe1—I1	100.07 (8)	C13—C14—Fe1	69.75 (17)
C12—Fe1—I1	116.66 (11)	C10—C14—H14	129 (2)
C11—Fe1—I1	90.48 (10)	C13—C14—H14	123 (2)
C3—Fe2—C4	93.83 (12)	Fe1—C14—H14	124 (2)
C3—Fe2—C23	113.11 (13)	C12—C11—C10	108.7 (3)
C4—Fe2—C23	96.55 (12)	C12—C11—Fe1	70.28 (18)
C3—Fe2—C24	89.69 (12)	C10—C11—Fe1	69.53 (16)
C4—Fe2—C24	131.68 (12)	C12—C11—H11	127 (2)
C23—Fe2—C24	39.69 (11)	C10—C11—H11	124 (2)
C3—Fe2—C22	152.70 (13)	Fe1—C11—H11	125 (2)
C4—Fe2—C22	93.09 (12)	C11—C12—C13	107.8 (3)
C23—Fe2—C22	39.77 (13)	C11—C12—Fe1	70.83 (18)
C24—Fe2—C22	66.28 (12)	C13—C12—Fe1	68.78 (18)
C3—Fe2—C20	103.95 (12)	C11—C12—H12	122 (2)
C4—Fe2—C20	159.18 (12)	C13—C12—H12	130 (2)
C23—Fe2—C20	66.69 (12)	Fe1—C12—H12	122 (2)
C24—Fe2—C20	39.60 (11)	C21—C20—C24	107.2 (3)
C22—Fe2—C20	66.17 (12)	C21—C20—Fe2	70.57 (16)
C3—Fe2—C21	142.27 (13)	C24—C20—Fe2	69.55 (16)
C4—Fe2—C21	123.90 (13)	C21—C20—H20	130 (2)
C23—Fe2—C21	66.18 (13)	C24—C20—H20	123 (2)
C24—Fe2—C21	65.84 (11)	Fe2—C20—H20	123 (2)
C22—Fe2—C21	39.11 (13)	C12—C13—C14	108.1 (3)
C20—Fe2—C21	39.18 (12)	C12—C13—Fe1	71.77 (19)
C3—Fe2—I2	90.55 (9)	C14—C13—Fe1	70.32 (17)
C4—Fe2—I2	89.18 (8)	C12—C13—H13	126 (2)
C23—Fe2—I2	155.09 (10)	C14—C13—H13	126 (2)
C24—Fe2—I2	139.02 (8)	Fe1—C13—H13	125 (2)
C22—Fe2—I2	115.93 (10)	C21—C22—C23	107.9 (3)
C20—Fe2—I2	101.22 (8)	C21—C22—Fe2	71.08 (17)
C21—Fe2—I2	90.51 (9)	C23—C22—Fe2	69.31 (17)
O1—C1—Fe1	178.9 (3)	C21—C22—H22	124 (2)
C24—C23—C22	107.8 (3)	C23—C22—H22	128 (2)
C24—C23—Fe2	70.78 (16)	Fe2—C22—H22	127 (2)

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Di­carbonyl­(η5-cyclo­penta­dienyl)­iodo­iron(II)

Supporting information

Key indicators

checkCIF/PLATON results

Dicarbonyl(η⁵-cyclopentadienyl)iodoiron(II)