Tricarbonyl­bis­(1,3-diisopropyl-4,5-dimethyl­imidazol-2-yl­idene)iron

Ahmida, A.; Flörke, U.; Henkel, G.

doi:10.1107/S1600536812048179

metal-organic compounds

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ISSN: 2056-9890

Volume 68| Part 12| December 2012| Page m1556

doi:10.1107/S1600536812048179

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Tricarbonylbis(1,3-diisopropyl-4,5-dimethylimidazol-2-ylidene)iron

Aziza Ahmida,^a Ulrich Flörke ^a ^* and Gerald Henkel ^a

^aDepartment Chemie, Fakultät für Naturwissenschaften, Universität Paderborn, Warburgerstrasse 100, D-33098 Paderborn, Germany
^*Correspondence e-mail: ulrich.floerke@upb.de

(Received 22 November 2012; accepted 23 November 2012; online 28 November 2012)

In the title compound, [Fe(C₁₁H₂₀N₂)₂(CO)₃], the Fe atom shows a distorted trigonal–bipyramidal geometry with three carbonyl and two carbene ligands. The latter have a cis arrangement, with a C—Fe—C angle of 90.60 (7)°. The Fe atom lies 0.007 (1) Å above the basal plane defined by two carbonyl and one carbene C atoms. The molecular structure is closely related to that of the isomolecular but not isotypic Ru complex with an identical cis arrangement, so, in general, bond geometries lie in expected ranges. In the crystal, C—H⋯O hydrogen bonds link the molecules into infinite zigzag chains extending along [010].

Related literature

For structures of related cis complexes, see: Ellul et al. (2008 ). For Co and Ru complexes with a trans configuration, see: van Rendsburg et al. (2007 ); Chantler et al. (2008 ); Ellul et al. (2008).

Experimental

Crystal data

[Fe(C₁₁H₂₀N₂)₂(CO)₃]
M_r = 500.46
Orthorhombic, P 2₁ 2₁ 2₁
a = 11.5913 (5) Å
b = 12.7572 (5) Å
c = 17.7970 (7) Å
V = 2631.69 (19) Å³
Z = 4
Mo Kα radiation
μ = 0.61 mm⁻¹
T = 120 K
0.38 × 0.32 × 0.29 mm

Data collection

Bruker SMART CCD area-detector diffractometer
Absorption correction: multi-scan (SADABS; Sheldrick, 2004 ) T_min = 0.803, T_max = 0.844
26635 measured reflections
6362 independent reflections
5983 reflections with I > 2σ(I)
R_int = 0.035

Refinement

R[F² > 2σ(F²)] = 0.033
wR(F²) = 0.082
S = 1.04
6362 reflections
298 parameters
H-atom parameters constrained
Δρ_max = 0.42 e Å⁻³
Δρ_min = −0.23 e Å⁻³
Absolute structure: Flack (1983 ), 2789 Friedel pairs
Flack parameter: 0.022 (11)

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C25—H25B⋯O2ⁱ	0.98	2.42	3.154 (3)	131
Symmetry code: (i) $[-x+1, y+{\script{1\over 2}}, -z+{\script{1\over 2}}]$ .

Data collection: SMART (Bruker, 2002 ); cell refinement: SAINT (Bruker, 2002); data reduction: SAINT; program(s) used to solve structure: SHELXTL (Sheldrick, 2008 ); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL and local programs.

Supporting information

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536812048179/bt6867sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536812048179/bt6867Isup2.hkl

checkCIF report

Related literature top

For structures of related cis complexes, see: Ellul et al. (2008). For Co and Rucomplexes with trans conformations, see: van Rendsburg et al. (2007); Chantler et al. (2008); Ellul et al. (2008).

Experimental top

To a solution of 1,3-diisopropyl-4,5-dimethylimidazol-2-thione (850 mg, 4 mmol) in 30 ml THF was added K (420 mg, 1 mmol + 10% excess) and the mixture was refluxed under inert atmosphere for 4 h. After filtration and removal of K₂S, Fe₂(CO)₉ (360 mg, 1 mmol) was added to the filtrate. The reaction mixture was stirred over night at room temperature. After removal of the solvent and subsequent drying in vacuum the residue was cyrstallized by diffusion of hexane into a concentrated toluene solution to give single-crystal of the title complex.

Computing details top

Data collection: SMART (Bruker, 2002); cell refinement: SAINT (Bruker, 2002); data reduction: SAINT (Bruker, 2002); program(s) used to solve structure: SHELXTL (Sheldrick, 2008); program(s) used to refine structure: SHELXTL (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXTL (Sheldrick, 2008) and local programs.

Figures top

	Fig. 1. Molecular structure of the title compound. Displacement ellipsoids are drawn at the 50% probability level.
	Fig. 2. Crystal packing viewed along [001] with hydrogen bonding pattern indicated as dashed lines. H-atoms not involved in bonding are omitted.

Tricarbonylbis(1,3-diisopropyl-4,5-dimethylimidazol-2-ylidene)iron top

Crystal data top

[Fe(C₁₁H₂₀N₂)₂(CO)₃]	F(000) = 1072
M_r = 500.46	D_x = 1.263 Mg m⁻³
Orthorhombic, P2₁2₁2₁	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2ac 2ab	Cell parameters from 7772 reflections
a = 11.5913 (5) Å	θ = 2.4–27.7°
b = 12.7572 (5) Å	µ = 0.61 mm⁻¹
c = 17.7970 (7) Å	T = 120 K
V = 2631.69 (19) Å³	Prism, yellow
Z = 4	0.38 × 0.32 × 0.29 mm

Data collection top

Bruker SMART CCD area-detector diffractometer	6362 independent reflections
Radiation source: sealed tube	5983 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.035
ϕ and ω scans	θ_max = 28.1°, θ_min = 2.0°
Absorption correction: multi-scan (SADABS; Sheldrick, 2004)	h = −15→15
T_min = 0.803, T_max = 0.844	k = −16→16
26635 measured reflections	l = −23→23

Refinement top

Refinement on F²	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: difference Fourier map
R[F² > 2σ(F²)] = 0.033	H-atom parameters constrained
wR(F²) = 0.082	w = 1/[σ²(F_o²) + (0.0461P)² + 0.1759P] where P = (F_o² + 2F_c²)/3
S = 1.04	(Δ/σ)_max = 0.002
6362 reflections	Δρ_max = 0.42 e Å⁻³
298 parameters	Δρ_min = −0.23 e Å⁻³
0 restraints	Absolute structure: Flack (1983), 2789 Friedel pairs
Primary atom site location: structure-invariant direct methods	Absolute structure parameter: 0.022 (11)

Crystal data top

[Fe(C₁₁H₂₀N₂)₂(CO)₃]	V = 2631.69 (19) Å³
M_r = 500.46	Z = 4
Orthorhombic, P2₁2₁2₁	Mo Kα radiation
a = 11.5913 (5) Å	µ = 0.61 mm⁻¹
b = 12.7572 (5) Å	T = 120 K
c = 17.7970 (7) Å	0.38 × 0.32 × 0.29 mm

Data collection top

Bruker SMART CCD area-detector diffractometer	6362 independent reflections
Absorption correction: multi-scan (SADABS; Sheldrick, 2004)	5983 reflections with I > 2σ(I)
T_min = 0.803, T_max = 0.844	R_int = 0.035
26635 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.033	H-atom parameters constrained
wR(F²) = 0.082	Δρ_max = 0.42 e Å⁻³
S = 1.04	Δρ_min = −0.23 e Å⁻³
6362 reflections	Absolute structure: Flack (1983), 2789 Friedel pairs
298 parameters	Absolute structure parameter: 0.022 (11)
0 restraints

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
Fe1	0.378885 (18)	0.495342 (17)	0.430547 (11)	0.01450 (6)
O1	0.34212 (13)	0.66917 (12)	0.32606 (8)	0.0353 (4)
O2	0.37267 (15)	0.28447 (11)	0.36881 (9)	0.0422 (4)
O3	0.12817 (10)	0.49640 (11)	0.43365 (7)	0.0306 (3)
N1	0.34487 (13)	0.52000 (12)	0.60226 (8)	0.0216 (3)
N2	0.45810 (13)	0.63918 (11)	0.55801 (9)	0.0219 (3)
N3	0.62444 (13)	0.43646 (11)	0.47979 (7)	0.0181 (3)
N4	0.62449 (12)	0.49072 (12)	0.36536 (8)	0.0216 (3)
C1	0.36558 (16)	0.60380 (14)	0.36833 (10)	0.0213 (3)
C2	0.37532 (17)	0.36667 (14)	0.39603 (10)	0.0229 (4)
C3	0.22766 (14)	0.49610 (14)	0.43548 (9)	0.0199 (3)
C4	0.39480 (14)	0.55369 (13)	0.53668 (9)	0.0171 (3)
C5	0.26875 (16)	0.42794 (16)	0.60580 (11)	0.0251 (4)
H5A	0.2674	0.3977	0.5540	0.030*
C6	0.14431 (18)	0.45811 (19)	0.62406 (13)	0.0364 (5)
H6A	0.1193	0.5145	0.5904	0.055*
H6B	0.1396	0.4822	0.6762	0.055*
H6C	0.0942	0.3970	0.6173	0.055*
C7	0.3120 (2)	0.34124 (18)	0.65709 (13)	0.0370 (5)
H7A	0.3918	0.3238	0.6439	0.056*
H7B	0.2633	0.2790	0.6510	0.056*
H7C	0.3088	0.3650	0.7094	0.056*
C8	0.3765 (2)	0.58435 (17)	0.66267 (10)	0.0324 (4)
C9	0.3397 (3)	0.5679 (3)	0.74274 (13)	0.0557 (8)
H9A	0.3625	0.6286	0.7730	0.084*
H9B	0.3768	0.5047	0.7627	0.084*
H9C	0.2557	0.5595	0.7448	0.084*
C10	0.44711 (19)	0.65845 (16)	0.63532 (11)	0.0311 (5)
C11	0.5096 (3)	0.74236 (19)	0.67739 (14)	0.0511 (7)
H11A	0.4736	0.7521	0.7267	0.077*
H11B	0.5058	0.8081	0.6490	0.077*
H11C	0.5905	0.7219	0.6840	0.077*
C12	0.52171 (16)	0.70393 (14)	0.50370 (12)	0.0255 (4)
H12A	0.5184	0.6652	0.4549	0.031*
C13	0.64936 (17)	0.71613 (17)	0.52206 (15)	0.0382 (5)
H13A	0.6839	0.6468	0.5295	0.057*
H13B	0.6580	0.7577	0.5680	0.057*
H13C	0.6884	0.7518	0.4804	0.057*
C14	0.46139 (18)	0.80827 (16)	0.48996 (14)	0.0370 (5)
H14A	0.3798	0.7957	0.4786	0.055*
H14B	0.4979	0.8441	0.4474	0.055*
H14C	0.4677	0.8521	0.5350	0.055*
C15	0.55252 (14)	0.47282 (12)	0.42458 (10)	0.0170 (3)
C16	0.58137 (15)	0.38014 (14)	0.54622 (10)	0.0199 (4)
H16A	0.4960	0.3912	0.5475	0.024*
C17	0.60057 (17)	0.26248 (14)	0.53661 (12)	0.0293 (4)
H17A	0.5680	0.2397	0.4885	0.044*
H17B	0.5626	0.2248	0.5777	0.044*
H17C	0.6835	0.2475	0.5375	0.044*
C18	0.62846 (19)	0.42159 (16)	0.62020 (10)	0.0291 (4)
H18A	0.6133	0.4970	0.6238	0.044*
H18B	0.7118	0.4092	0.6225	0.044*
H18C	0.5907	0.3853	0.6620	0.044*
C19	0.73965 (15)	0.43699 (15)	0.45598 (11)	0.0226 (4)
C20	0.84120 (17)	0.41219 (19)	0.50418 (13)	0.0359 (5)
H20A	0.9120	0.4184	0.4744	0.054*
H20B	0.8342	0.3405	0.5234	0.054*
H20C	0.8442	0.4614	0.5464	0.054*
C21	0.73951 (15)	0.47107 (14)	0.38450 (10)	0.0238 (4)
C22	0.84160 (17)	0.4855 (2)	0.33430 (13)	0.0413 (6)
H22A	0.9121	0.4874	0.3647	0.062*
H22B	0.8338	0.5515	0.3066	0.062*
H22C	0.8459	0.4270	0.2987	0.062*
C23	0.58288 (17)	0.51908 (17)	0.28977 (10)	0.0306 (5)
H23A	0.4967	0.5168	0.2921	0.037*
C24	0.6189 (2)	0.4380 (3)	0.23116 (12)	0.0501 (7)
H24A	0.5947	0.3681	0.2477	0.075*
H24B	0.7029	0.4394	0.2252	0.075*
H24C	0.5822	0.4545	0.1830	0.075*
C25	0.6150 (2)	0.6308 (2)	0.26977 (15)	0.0508 (7)
H25A	0.5880	0.6782	0.3094	0.076*
H25B	0.5786	0.6500	0.2220	0.076*
H25C	0.6990	0.6365	0.2650	0.076*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Fe1	0.01323 (11)	0.01603 (11)	0.01422 (10)	−0.00051 (10)	−0.00024 (8)	0.00020 (10)
O1	0.0401 (9)	0.0333 (8)	0.0325 (8)	0.0048 (7)	−0.0021 (6)	0.0136 (6)
O2	0.0557 (10)	0.0268 (7)	0.0442 (8)	−0.0075 (8)	0.0135 (9)	−0.0155 (6)
O3	0.0164 (6)	0.0346 (7)	0.0407 (7)	0.0008 (7)	−0.0010 (5)	−0.0029 (7)
N1	0.0227 (7)	0.0253 (8)	0.0167 (7)	0.0028 (6)	0.0016 (5)	−0.0029 (6)
N2	0.0211 (7)	0.0203 (7)	0.0243 (8)	−0.0004 (6)	−0.0042 (6)	−0.0048 (6)
N3	0.0149 (7)	0.0202 (7)	0.0194 (7)	0.0003 (6)	0.0004 (6)	0.0015 (5)
N4	0.0177 (6)	0.0279 (7)	0.0191 (6)	0.0005 (8)	0.0024 (5)	0.0027 (6)
C1	0.0201 (9)	0.0236 (9)	0.0202 (8)	−0.0013 (7)	−0.0023 (7)	0.0023 (7)
C2	0.0218 (9)	0.0249 (9)	0.0220 (8)	−0.0010 (8)	0.0038 (8)	−0.0013 (7)
C3	0.0209 (7)	0.0179 (7)	0.0208 (7)	0.0006 (7)	−0.0004 (6)	−0.0014 (9)
C4	0.0137 (8)	0.0172 (8)	0.0203 (8)	0.0031 (6)	−0.0014 (6)	0.0005 (6)
C5	0.0243 (9)	0.0293 (10)	0.0218 (9)	0.0005 (8)	0.0045 (7)	0.0056 (8)
C6	0.0262 (11)	0.0460 (13)	0.0370 (11)	0.0031 (9)	0.0090 (9)	0.0084 (10)
C7	0.0353 (11)	0.0424 (13)	0.0333 (11)	0.0047 (10)	0.0089 (9)	0.0162 (9)
C8	0.0376 (11)	0.0395 (11)	0.0201 (9)	0.0073 (10)	−0.0003 (9)	−0.0089 (8)
C9	0.0736 (19)	0.0734 (19)	0.0201 (10)	−0.0006 (15)	0.0049 (11)	−0.0119 (12)
C10	0.0366 (11)	0.0313 (11)	0.0254 (10)	0.0060 (9)	−0.0067 (9)	−0.0118 (8)
C11	0.0654 (18)	0.0458 (14)	0.0423 (13)	−0.0033 (13)	−0.0141 (13)	−0.0228 (12)
C12	0.0206 (9)	0.0199 (9)	0.0359 (10)	−0.0048 (7)	−0.0035 (8)	−0.0017 (8)
C13	0.0229 (10)	0.0269 (10)	0.0649 (16)	−0.0025 (8)	−0.0079 (10)	−0.0019 (10)
C14	0.0249 (10)	0.0243 (10)	0.0618 (15)	−0.0021 (8)	−0.0080 (10)	0.0063 (10)
C15	0.0180 (8)	0.0160 (8)	0.0170 (7)	−0.0007 (6)	0.0002 (6)	−0.0007 (6)
C16	0.0186 (8)	0.0219 (9)	0.0193 (8)	0.0027 (7)	−0.0011 (7)	0.0059 (7)
C17	0.0264 (10)	0.0213 (9)	0.0402 (11)	0.0005 (7)	0.0010 (9)	0.0066 (8)
C18	0.0313 (10)	0.0353 (10)	0.0206 (9)	0.0035 (9)	−0.0040 (8)	0.0029 (7)
C19	0.0155 (8)	0.0225 (9)	0.0297 (9)	0.0003 (7)	0.0010 (7)	0.0002 (7)
C20	0.0183 (9)	0.0495 (13)	0.0399 (12)	0.0017 (9)	−0.0019 (8)	0.0084 (10)
C21	0.0168 (8)	0.0278 (10)	0.0267 (9)	0.0004 (7)	0.0039 (7)	0.0005 (7)
C22	0.0213 (9)	0.0639 (17)	0.0387 (11)	−0.0045 (10)	0.0093 (8)	0.0062 (12)
C23	0.0256 (9)	0.0482 (13)	0.0179 (8)	0.0050 (9)	0.0050 (7)	0.0080 (8)
C24	0.0374 (13)	0.088 (2)	0.0252 (11)	0.0085 (15)	0.0011 (11)	−0.0116 (12)
C25	0.0413 (13)	0.0592 (15)	0.0518 (14)	0.0049 (13)	0.0092 (12)	0.0319 (12)

Geometric parameters (Å, º) top

Fe1—C2	1.7531 (18)	C11—H11C	0.9800
Fe1—C3	1.7551 (16)	C12—C13	1.523 (3)
Fe1—C1	1.7788 (17)	C12—C14	1.523 (3)
Fe1—C15	2.0358 (16)	C12—H12A	1.0000
Fe1—C4	2.0386 (17)	C13—H13A	0.9800
O1—C1	1.156 (2)	C13—H13B	0.9800
O2—C2	1.156 (2)	C13—H13C	0.9800
O3—C3	1.154 (2)	C14—H14A	0.9800
N1—C4	1.372 (2)	C14—H14B	0.9800
N1—C8	1.402 (2)	C14—H14C	0.9800
N1—C5	1.470 (2)	C16—C18	1.520 (3)
N2—C4	1.368 (2)	C16—C17	1.527 (2)
N2—C10	1.403 (2)	C16—H16A	1.0000
N2—C12	1.470 (2)	C17—H17A	0.9800
N3—C15	1.369 (2)	C17—H17B	0.9800
N3—C19	1.401 (2)	C17—H17C	0.9800
N3—C16	1.471 (2)	C18—H18A	0.9800
N4—C15	1.363 (2)	C18—H18B	0.9800
N4—C21	1.399 (2)	C18—H18C	0.9800
N4—C23	1.474 (2)	C19—C21	1.344 (3)
C5—C7	1.519 (3)	C19—C20	1.491 (3)
C5—C6	1.528 (3)	C20—H20A	0.9800
C5—H5A	1.0000	C20—H20B	0.9800
C6—H6A	0.9800	C20—H20C	0.9800
C6—H6B	0.9800	C21—C22	1.494 (3)
C6—H6C	0.9800	C22—H22A	0.9800
C7—H7A	0.9800	C22—H22B	0.9800
C7—H7B	0.9800	C22—H22C	0.9800
C7—H7C	0.9800	C23—C25	1.515 (3)
C8—C10	1.342 (3)	C23—C24	1.527 (3)
C8—C9	1.502 (3)	C23—H23A	1.0000
C9—H9A	0.9800	C24—H24A	0.9800
C9—H9B	0.9800	C24—H24B	0.9800
C9—H9C	0.9800	C24—H24C	0.9800
C10—C11	1.494 (3)	C25—H25A	0.9800
C11—H11A	0.9800	C25—H25B	0.9800
C11—H11B	0.9800	C25—H25C	0.9800

C2—Fe1—C3	89.95 (9)	C12—C13—H13A	109.5
C2—Fe1—C1	120.54 (9)	C12—C13—H13B	109.5
C3—Fe1—C1	86.58 (8)	H13A—C13—H13B	109.5
C2—Fe1—C15	82.70 (8)	C12—C13—H13C	109.5
C3—Fe1—C15	172.20 (8)	H13A—C13—H13C	109.5
C1—Fe1—C15	99.38 (8)	H13B—C13—H13C	109.5
C2—Fe1—C4	131.97 (7)	C12—C14—H14A	109.5
C3—Fe1—C4	92.41 (7)	C12—C14—H14B	109.5
C1—Fe1—C4	107.49 (7)	H14A—C14—H14B	109.5
C15—Fe1—C4	90.60 (7)	C12—C14—H14C	109.5
C4—N1—C8	111.02 (15)	H14A—C14—H14C	109.5
C4—N1—C5	122.68 (14)	H14B—C14—H14C	109.5
C8—N1—C5	126.30 (16)	N4—C15—N3	103.82 (13)
C4—N2—C10	111.29 (16)	N4—C15—Fe1	128.43 (12)
C4—N2—C12	122.31 (15)	N3—C15—Fe1	127.75 (12)
C10—N2—C12	126.29 (16)	N3—C16—C18	113.85 (15)
C15—N3—C19	111.20 (14)	N3—C16—C17	109.91 (15)
C15—N3—C16	122.38 (14)	C18—C16—C17	112.75 (15)
C19—N3—C16	124.68 (14)	N3—C16—H16A	106.6
C15—N4—C21	111.40 (14)	C18—C16—H16A	106.6
C15—N4—C23	123.11 (14)	C17—C16—H16A	106.6
C21—N4—C23	125.32 (14)	C16—C17—H17A	109.5
O1—C1—Fe1	170.74 (17)	C16—C17—H17B	109.5
O2—C2—Fe1	175.73 (17)	H17A—C17—H17B	109.5
O3—C3—Fe1	175.51 (15)	C16—C17—H17C	109.5
N2—C4—N1	103.88 (14)	H17A—C17—H17C	109.5
N2—C4—Fe1	126.64 (12)	H17B—C17—H17C	109.5
N1—C4—Fe1	129.47 (12)	C16—C18—H18A	109.5
N1—C5—C7	114.16 (17)	C16—C18—H18B	109.5
N1—C5—C6	111.99 (17)	H18A—C18—H18B	109.5
C7—C5—C6	111.54 (16)	C16—C18—H18C	109.5
N1—C5—H5A	106.2	H18A—C18—H18C	109.5
C7—C5—H5A	106.2	H18B—C18—H18C	109.5
C6—C5—H5A	106.2	C21—C19—N3	106.66 (15)
C5—C6—H6A	109.5	C21—C19—C20	127.89 (17)
C5—C6—H6B	109.5	N3—C19—C20	125.29 (17)
H6A—C6—H6B	109.5	C19—C20—H20A	109.5
C5—C6—H6C	109.5	C19—C20—H20B	109.5
H6A—C6—H6C	109.5	H20A—C20—H20B	109.5
H6B—C6—H6C	109.5	C19—C20—H20C	109.5
C5—C7—H7A	109.5	H20A—C20—H20C	109.5
C5—C7—H7B	109.5	H20B—C20—H20C	109.5
H7A—C7—H7B	109.5	C19—C21—N4	106.83 (15)
C5—C7—H7C	109.5	C19—C21—C22	127.21 (18)
H7A—C7—H7C	109.5	N4—C21—C22	125.96 (17)
H7B—C7—H7C	109.5	C21—C22—H22A	109.5
C10—C8—N1	107.09 (16)	C21—C22—H22B	109.5
C10—C8—C9	128.0 (2)	H22A—C22—H22B	109.5
N1—C8—C9	124.8 (2)	C21—C22—H22C	109.5
C8—C9—H9A	109.5	H22A—C22—H22C	109.5
C8—C9—H9B	109.5	H22B—C22—H22C	109.5
H9A—C9—H9B	109.5	N4—C23—C25	111.40 (18)
C8—C9—H9C	109.5	N4—C23—C24	111.58 (18)
H9A—C9—H9C	109.5	C25—C23—C24	114.18 (19)
H9B—C9—H9C	109.5	N4—C23—H23A	106.4
C8—C10—N2	106.71 (17)	C25—C23—H23A	106.4
C8—C10—C11	128.2 (2)	C24—C23—H23A	106.4
N2—C10—C11	125.0 (2)	C23—C24—H24A	109.5
C10—C11—H11A	109.5	C23—C24—H24B	109.5
C10—C11—H11B	109.5	H24A—C24—H24B	109.5
H11A—C11—H11B	109.5	C23—C24—H24C	109.5
C10—C11—H11C	109.5	H24A—C24—H24C	109.5
H11A—C11—H11C	109.5	H24B—C24—H24C	109.5
H11B—C11—H11C	109.5	C23—C25—H25A	109.5
N2—C12—C13	113.80 (17)	C23—C25—H25B	109.5
N2—C12—C14	111.49 (16)	H25A—C25—H25B	109.5
C13—C12—C14	113.02 (16)	C23—C25—H25C	109.5
N2—C12—H12A	105.9	H25A—C25—H25C	109.5
C13—C12—H12A	105.9	H25B—C25—H25C	109.5
C14—C12—H12A	105.9

C10—N2—C4—N1	−0.31 (19)	C10—N2—C12—C14	−70.2 (2)
C12—N2—C4—N1	−176.57 (15)	C21—N4—C15—N3	−3.00 (19)
C10—N2—C4—Fe1	178.52 (13)	C23—N4—C15—N3	172.56 (16)
C12—N2—C4—Fe1	2.3 (2)	C21—N4—C15—Fe1	176.66 (12)
C8—N1—C4—N2	0.41 (19)	C23—N4—C15—Fe1	−7.8 (2)
C5—N1—C4—N2	−179.58 (15)	C19—N3—C15—N4	2.90 (19)
C8—N1—C4—Fe1	−178.37 (13)	C16—N3—C15—N4	−162.70 (14)
C5—N1—C4—Fe1	1.6 (2)	C19—N3—C15—Fe1	−176.76 (12)
C2—Fe1—C4—N2	140.02 (15)	C16—N3—C15—Fe1	17.6 (2)
C3—Fe1—C4—N2	−127.88 (15)	C2—Fe1—C15—N4	88.48 (16)
C1—Fe1—C4—N2	−40.71 (16)	C1—Fe1—C15—N4	−31.39 (16)
C15—Fe1—C4—N2	59.32 (15)	C4—Fe1—C15—N4	−139.23 (15)
C2—Fe1—C4—N1	−41.4 (2)	C2—Fe1—C15—N3	−91.94 (15)
C3—Fe1—C4—N1	50.66 (16)	C1—Fe1—C15—N3	148.19 (15)
C1—Fe1—C4—N1	137.83 (15)	C4—Fe1—C15—N3	40.35 (15)
C15—Fe1—C4—N1	−122.14 (15)	C15—N3—C16—C18	−130.89 (17)
C4—N1—C5—C7	119.58 (19)	C19—N3—C16—C18	65.5 (2)
C8—N1—C5—C7	−60.4 (2)	C15—N3—C16—C17	101.53 (18)
C4—N1—C5—C6	−112.46 (19)	C19—N3—C16—C17	−62.1 (2)
C8—N1—C5—C6	67.5 (2)	C15—N3—C19—C21	−1.8 (2)
C4—N1—C8—C10	−0.4 (2)	C16—N3—C19—C21	163.43 (16)
C5—N1—C8—C10	179.62 (17)	C15—N3—C19—C20	173.86 (18)
C4—N1—C8—C9	−178.3 (2)	C16—N3—C19—C20	−20.9 (3)
C5—N1—C8—C9	1.7 (3)	N3—C19—C21—N4	−0.1 (2)
N1—C8—C10—N2	0.2 (2)	C20—C19—C21—N4	−175.63 (19)
C9—C8—C10—N2	178.0 (2)	N3—C19—C21—C22	180.0 (2)
N1—C8—C10—C11	−176.3 (2)	C20—C19—C21—C22	4.5 (3)
C9—C8—C10—C11	1.5 (4)	C15—N4—C21—C19	2.0 (2)
C4—N2—C10—C8	0.1 (2)	C23—N4—C21—C19	−173.42 (18)
C12—N2—C10—C8	176.17 (17)	C15—N4—C21—C22	−178.07 (19)
C4—N2—C10—C11	176.7 (2)	C23—N4—C21—C22	6.5 (3)
C12—N2—C10—C11	−7.2 (3)	C15—N4—C23—C25	111.8 (2)
C4—N2—C12—C13	−125.24 (19)	C21—N4—C23—C25	−73.2 (2)
C10—N2—C12—C13	59.1 (2)	C15—N4—C23—C24	−119.3 (2)
C4—N2—C12—C14	105.49 (19)	C21—N4—C23—C24	55.7 (3)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C25—H25B···O2ⁱ	0.98	2.42	3.154 (3)	131

Symmetry code: (i) −x+1, y+1/2, −z+1/2.

Experimental details

Crystal data
Chemical formula	[Fe(C₁₁H₂₀N₂)₂(CO)₃]
M_r	500.46
Crystal system, space group	Orthorhombic, P2₁2₁2₁
Temperature (K)	120
a, b, c (Å)	11.5913 (5), 12.7572 (5), 17.7970 (7)
V (Å³)	2631.69 (19)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.61
Crystal size (mm)	0.38 × 0.32 × 0.29

Data collection
Diffractometer	Bruker SMART CCD area-detector diffractometer
Absorption correction	Multi-scan (SADABS; Sheldrick, 2004)
T_min, T_max	0.803, 0.844
No. of measured, independent and observed [I > 2σ(I)] reflections	26635, 6362, 5983
R_int	0.035
(sin θ/λ)_max (Å⁻¹)	0.662

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.033, 0.082, 1.04
No. of reflections	6362
No. of parameters	298
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.42, −0.23
Absolute structure	Flack (1983), 2789 Friedel pairs
Absolute structure parameter	0.022 (11)

Computer programs: SMART (Bruker, 2002), SAINT (Bruker, 2002), SHELXTL (Sheldrick, 2008) and local programs.

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C25—H25B···O2ⁱ	0.98	2.42	3.154 (3)	131.0

Symmetry code: (i) −x+1, y+1/2, −z+1/2.

References

Bruker (2002). SMART and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
Chantler, V. L., Chatwin, S. L., Jazzar, R. F. R., Mahon, M. F., Saker, O. & Whittlesey, M. K. (2008). Dalton Trans. pp. 2603–2614. Web of Science CSD CrossRef Google Scholar
Ellul, C. E., Saker, O., Mahon, M. F., Apperley, D. C. & Whittlesey, M. K. (2008). Organometallics, 27, 100–108. Web of Science CSD CrossRef CAS Google Scholar
Flack, H. D. (1983). Acta Cryst. A39, 876–881. CrossRef CAS Web of Science IUCr Journals Google Scholar
Rendsburg, H. van, Tooze, R. P., Foster, D. F. & Otto, S. (2007). Inorg. Chem. 46, 1963–1965. Web of Science PubMed Google Scholar
Sheldrick, G. M. (2004). SADABS. University of Göttingen, Germany. Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar

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Volume 68| Part 12| December 2012| Page m1556

doi:10.1107/S1600536812048179

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