metal-organic compounds
Tricarbonylbis(1,3-diisopropyl-4,5-dimethylimidazol-2-ylidene)iron
aDepartment Chemie, Fakultät für Naturwissenschaften, Universität Paderborn, Warburgerstrasse 100, D-33098 Paderborn, Germany
*Correspondence e-mail: ulrich.floerke@upb.de
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
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Data collection: SMART (Bruker, 2002); cell 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
10.1107/S1600536812048179/bt6867sup1.cif
contains datablocks I, global. DOI:Structure factors: contains datablock I. DOI: 10.1107/S1600536812048179/bt6867Isup2.hkl
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.
All Hydrogen atom positions were clearly derived from difference maps, then refined at calculated positions riding on the parent atoms with C—H 0.98 - 1.00 Å and isotropic displacement parameters Uiso(H) = 1.2U(Ceq) or 1.5U(–CH3). All CH3 hydrogen atoms were allowed to rotate but not to tip.
Data collection: SMART (Bruker, 2002); cell
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.[Fe(C11H20N2)2(CO)3] | F(000) = 1072 |
Mr = 500.46 | Dx = 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 |
Bruker SMART CCD area-detector diffractometer | 6362 independent reflections |
Radiation source: sealed tube | 5983 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.035 |
ϕ and ω scans | θmax = 28.1°, θmin = 2.0° |
Absorption correction: multi-scan (SADABS; Sheldrick, 2004) | h = −15→15 |
Tmin = 0.803, Tmax = 0.844 | k = −16→16 |
26635 measured reflections | l = −23→23 |
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(Fo2) + (0.0461P)2 + 0.1759P] where P = (Fo2 + 2Fc2)/3 |
S = 1.04 | (Δ/σ)max = 0.002 |
6362 reflections | Δρmax = 0.42 e Å−3 |
298 parameters | Δρmin = −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) |
[Fe(C11H20N2)2(CO)3] | V = 2631.69 (19) Å3 |
Mr = 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 |
Bruker SMART CCD area-detector diffractometer | 6362 independent reflections |
Absorption correction: multi-scan (SADABS; Sheldrick, 2004) | 5983 reflections with I > 2σ(I) |
Tmin = 0.803, Tmax = 0.844 | Rint = 0.035 |
26635 measured reflections |
R[F2 > 2σ(F2)] = 0.033 | H-atom parameters constrained |
wR(F2) = 0.082 | Δρmax = 0.42 e Å−3 |
S = 1.04 | Δρmin = −0.23 e Å−3 |
6362 reflections | Absolute structure: Flack (1983), 2789 Friedel pairs |
298 parameters | Absolute structure parameter: 0.022 (11) |
0 restraints |
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. |
x | y | z | Uiso*/Ueq | ||
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* |
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) |
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) |
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] |
Mr | 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) |
Tmin, Tmax | 0.803, 0.844 |
No. of measured, independent and observed [I > 2σ(I)] reflections | 26635, 6362, 5983 |
Rint | 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 |
Δρmax, Δρmin (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.
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
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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
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