The aurophilicity exhibited by AuI complexes depends strongly on the nature of the supporting ligands present and the length of the Au–element (Au—E) bond may be used as a measure of the donor–acceptor properties of the coordinated ligands. A binuclear iron–gold complex, [1,3-bis(2,6-diisopropylphenyl)imidazol-2-ylidene-2κC2]dicarbonyl-1κ2C-(1η5-cyclopentadienyl)gold(I)iron(II)(Au—Fe) benzene trisolvate, [AuFe(C5H5)(C27H36N2)(CO)2]·3C6H6, was prepared by reaction of K[CpFe(CO)2] (Cp is cyclopentadienyl) with (NHC)AuCl [NHC = 1,3-bis(2,6-diisopropylphenyl)imidazol-2-ylidene]. In addition to the binuclear complex, the asymmetric unit contains three benzene solvent molecules. This is the first example of a two-coordinated Au atom bonded to an Fe and a C atom of an N-heterocyclic carbene.
Supporting information
CCDC reference: 1063870
Data collection: X-AREA (Stoe & Cie, 2001); cell refinement: X-AREA (Stoe & Cie, 2001); data reduction: X-AREA (Stoe & Cie, 2001); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL2014 (Sheldrick, 2015); molecular graphics: XP (Sheldrick, 2008) and Mercury (Macrae et al., 2006); software used to prepare material for publication: publCIF (Westrip, 2010).
[1,3-Bis(2,6-diisopropylphenyl)imidazol-2-ylidene-2
κC2]dicarbonyl-1
κC-(1
η5-cyclopentadienyl)gold(0)iron(II)(
Au—
Fe)
benzene trisolvate
top
Crystal data top
[AuFe(C5H5)(C27H36N2)(CO)2]·3C6H6 | Z = 2 |
Mr = 996.82 | F(000) = 1012 |
Triclinic, P1 | Dx = 1.416 Mg m−3 |
a = 10.0579 (4) Å | Mo Kα radiation, λ = 0.71073 Å |
b = 16.3027 (6) Å | Cell parameters from 58383 reflections |
c = 16.7074 (6) Å | θ = 2.7–30.2° |
α = 110.037 (3)° | µ = 3.48 mm−1 |
β = 104.524 (3)° | T = 173 K |
γ = 103.208 (3)° | Block, light yellow |
V = 2337.83 (16) Å3 | 0.26 × 0.24 × 0.21 mm |
Data collection top
STOE IPDS II two-circle- diffractometer | 12614 reflections with I > 2σ(I) |
Radiation source: Genix 3D IµS microfocus X-ray source | Rint = 0.082 |
ω scans | θmax = 29.8°, θmin = 2.7° |
Absorption correction: multi-scan X-Area (Stoe & Cie, 2001) | h = −13→14 |
Tmin = 0.356, Tmax = 0.477 | k = −22→22 |
58383 measured reflections | l = −23→23 |
13245 independent reflections | |
Refinement top
Refinement on F2 | Hydrogen site location: inferred from neighbouring sites |
Least-squares matrix: full | H-atom parameters constrained |
R[F2 > 2σ(F2)] = 0.033 | w = 1/[σ2(Fo2) + (0.0483P)2 + 1.1822P] where P = (Fo2 + 2Fc2)/3 |
wR(F2) = 0.088 | (Δ/σ)max = 0.002 |
S = 1.08 | Δρmax = 1.40 e Å−3 |
13245 reflections | Δρmin = −2.08 e Å−3 |
524 parameters | Extinction correction: SHELXL, Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4 |
12 restraints | Extinction coefficient: 0.0136 (5) |
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. |
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top | x | y | z | Uiso*/Ueq | |
Au1 | 0.37489 (2) | 0.33945 (2) | 0.21016 (2) | 0.02569 (5) | |
Fe1 | 0.18305 (4) | 0.41298 (3) | 0.18829 (3) | 0.02917 (8) | |
C1 | 0.0793 (3) | 0.2953 (2) | 0.1246 (2) | 0.0358 (6) | |
O1 | 0.0059 (3) | 0.21830 (19) | 0.08102 (19) | 0.0525 (7) | |
C2 | 0.1858 (4) | 0.4120 (2) | 0.2920 (2) | 0.0380 (6) | |
O2 | 0.1849 (4) | 0.4145 (2) | 0.36216 (18) | 0.0592 (7) | |
C11 | 0.5482 (3) | 0.29580 (17) | 0.22389 (16) | 0.0225 (4) | |
N12 | 0.6730 (2) | 0.33670 (15) | 0.21310 (15) | 0.0256 (4) | |
C13 | 0.7739 (3) | 0.2930 (2) | 0.2268 (2) | 0.0314 (5) | |
H13A | 0.8686 | 0.3088 | 0.2233 | 0.038* | |
C14 | 0.7108 (3) | 0.2234 (2) | 0.2460 (2) | 0.0325 (5) | |
H14A | 0.7523 | 0.1804 | 0.2587 | 0.039* | |
N15 | 0.5738 (2) | 0.22680 (15) | 0.24362 (15) | 0.0246 (4) | |
C21 | 0.2042 (5) | 0.4542 (3) | 0.0856 (3) | 0.0554 (10) | |
H21A | 0.1959 | 0.4125 | 0.0232 | 0.066* | |
C22 | 0.3344 (4) | 0.5042 (3) | 0.1624 (3) | 0.0481 (8) | |
H22A | 0.4348 | 0.5044 | 0.1648 | 0.058* | |
C23 | 0.2972 (5) | 0.5542 (2) | 0.2346 (3) | 0.0521 (9) | |
H23A | 0.3669 | 0.5972 | 0.2981 | 0.063* | |
C24 | 0.1449 (6) | 0.5366 (3) | 0.2017 (4) | 0.0666 (13) | |
H24A | 0.0886 | 0.5648 | 0.2379 | 0.080* | |
C25 | 0.0881 (5) | 0.4757 (3) | 0.1108 (4) | 0.0664 (14) | |
H25A | −0.0165 | 0.4520 | 0.0694 | 0.080* | |
C31 | 0.6981 (3) | 0.41725 (19) | 0.19382 (19) | 0.0283 (5) | |
C32 | 0.6605 (3) | 0.4033 (2) | 0.1025 (2) | 0.0336 (6) | |
C33 | 0.6875 (4) | 0.4832 (3) | 0.0861 (2) | 0.0428 (7) | |
H33A | 0.6626 | 0.4769 | 0.0251 | 0.051* | |
C34 | 0.7498 (4) | 0.5709 (3) | 0.1575 (3) | 0.0457 (8) | |
H34A | 0.7689 | 0.6242 | 0.1451 | 0.055* | |
C35 | 0.7847 (4) | 0.5819 (2) | 0.2468 (3) | 0.0417 (7) | |
H35A | 0.8260 | 0.6427 | 0.2951 | 0.050* | |
C36 | 0.7600 (3) | 0.5047 (2) | 0.2672 (2) | 0.0334 (5) | |
C37 | 0.5924 (4) | 0.3074 (2) | 0.0242 (2) | 0.0395 (6) | |
H37A | 0.5878 | 0.2609 | 0.0509 | 0.047* | |
C371 | 0.6846 (5) | 0.2915 (3) | −0.0351 (3) | 0.0612 (11) | |
H37B | 0.6375 | 0.2288 | −0.0851 | 0.092* | |
H37C | 0.6938 | 0.3377 | −0.0605 | 0.092* | |
H37D | 0.7820 | 0.2977 | 0.0019 | 0.092* | |
C372 | 0.4370 (5) | 0.2908 (5) | −0.0326 (4) | 0.0847 (18) | |
H37E | 0.3956 | 0.2283 | −0.0828 | 0.127* | |
H37F | 0.3773 | 0.2964 | 0.0059 | 0.127* | |
H37G | 0.4378 | 0.3371 | −0.0577 | 0.127* | |
C38 | 0.7932 (4) | 0.5178 (2) | 0.3658 (2) | 0.0391 (6) | |
H38A | 0.7735 | 0.4547 | 0.3656 | 0.047* | |
C381 | 0.9552 (4) | 0.5754 (3) | 0.4253 (3) | 0.0591 (10) | |
H38B | 0.9723 | 0.5823 | 0.4880 | 0.089* | |
H38C | 1.0174 | 0.5436 | 0.4007 | 0.089* | |
H38D | 0.9788 | 0.6370 | 0.4249 | 0.089* | |
C382 | 0.6916 (5) | 0.5606 (3) | 0.4051 (2) | 0.0503 (8) | |
H38E | 0.7143 | 0.5685 | 0.4684 | 0.075* | |
H38F | 0.7050 | 0.6213 | 0.4033 | 0.075* | |
H38G | 0.5898 | 0.5195 | 0.3688 | 0.075* | |
C41 | 0.4722 (3) | 0.16264 (19) | 0.2612 (2) | 0.0292 (5) | |
C42 | 0.3728 (3) | 0.0801 (2) | 0.1883 (2) | 0.0367 (6) | |
C43 | 0.2775 (4) | 0.0193 (2) | 0.2077 (3) | 0.0472 (8) | |
H43A | 0.2086 | −0.0376 | 0.1594 | 0.057* | |
C44 | 0.2818 (4) | 0.0405 (3) | 0.2957 (3) | 0.0518 (9) | |
H44A | 0.2159 | −0.0017 | 0.3076 | 0.062* | |
C45 | 0.3814 (4) | 0.1226 (3) | 0.3668 (3) | 0.0478 (8) | |
H45A | 0.3830 | 0.1364 | 0.4272 | 0.057* | |
C46 | 0.4794 (3) | 0.1856 (2) | 0.3514 (2) | 0.0351 (6) | |
C47 | 0.3627 (4) | 0.0580 (2) | 0.0903 (2) | 0.0465 (8) | |
H47A | 0.4528 | 0.1014 | 0.0922 | 0.056* | |
C471 | 0.3548 (6) | −0.0408 (3) | 0.0382 (4) | 0.0680 (13) | |
H47B | 0.3485 | −0.0510 | −0.0241 | 0.102* | |
H47C | 0.4428 | −0.0503 | 0.0690 | 0.102* | |
H47D | 0.2680 | −0.0847 | 0.0362 | 0.102* | |
C472 | 0.2304 (6) | 0.0767 (4) | 0.0410 (3) | 0.0709 (14) | |
H47E | 0.2374 | 0.1407 | 0.0756 | 0.106* | |
H47F | 0.2289 | 0.0680 | −0.0203 | 0.106* | |
H47G | 0.1402 | 0.0333 | 0.0361 | 0.106* | |
C48 | 0.5858 (4) | 0.2768 (3) | 0.4302 (2) | 0.0422 (7) | |
H48A | 0.6598 | 0.3053 | 0.4083 | 0.051* | |
C481 | 0.5068 (6) | 0.3441 (3) | 0.4595 (3) | 0.0678 (12) | |
H48B | 0.5769 | 0.4024 | 0.5102 | 0.102* | |
H48C | 0.4613 | 0.3569 | 0.4080 | 0.102* | |
H48D | 0.4309 | 0.3166 | 0.4791 | 0.102* | |
C482 | 0.6673 (5) | 0.2611 (4) | 0.5111 (3) | 0.0617 (11) | |
H48E | 0.7176 | 0.2175 | 0.4909 | 0.093* | |
H48F | 0.7392 | 0.3206 | 0.5590 | 0.093* | |
H48G | 0.5972 | 0.2353 | 0.5353 | 0.093* | |
C51 | 0.4722 (7) | 0.1568 (5) | 0.6799 (5) | 0.130 (4) | |
H51A | 0.5543 | 0.1862 | 0.7354 | 0.156* | |
C52 | 0.3730 (6) | 0.2019 (5) | 0.6625 (4) | 0.101 (2) | |
H52A | 0.3901 | 0.2631 | 0.7049 | 0.121* | |
C53 | 0.2491 (7) | 0.1571 (4) | 0.5829 (4) | 0.0853 (17) | |
H53A | 0.1809 | 0.1873 | 0.5714 | 0.102* | |
C54 | 0.2258 (6) | 0.0680 (4) | 0.5203 (4) | 0.0773 (15) | |
H54A | 0.1397 | 0.0368 | 0.4670 | 0.093* | |
C55 | 0.3273 (7) | 0.0242 (4) | 0.5349 (4) | 0.091 (2) | |
H55A | 0.3130 | −0.0354 | 0.4905 | 0.109* | |
C56 | 0.4503 (7) | 0.0684 (5) | 0.6154 (5) | 0.124 (4) | |
H56A | 0.5191 | 0.0385 | 0.6263 | 0.149* | |
C61 | −0.1549 (6) | 0.0347 (3) | 0.2269 (3) | 0.0610 (11) | |
H61A | −0.2235 | −0.0205 | 0.1763 | 0.073* | |
C62 | −0.1640 (7) | 0.0554 (4) | 0.3118 (4) | 0.0710 (14) | |
H62A | −0.2373 | 0.0150 | 0.3209 | 0.085* | |
C63 | −0.0623 (8) | 0.1377 (5) | 0.3845 (3) | 0.0814 (18) | |
H63A | −0.0667 | 0.1537 | 0.4438 | 0.098* | |
C64 | 0.0439 (6) | 0.1957 (4) | 0.3709 (3) | 0.0742 (16) | |
H64A | 0.1125 | 0.2516 | 0.4206 | 0.089* | |
C65 | 0.0500 (5) | 0.1723 (3) | 0.2858 (3) | 0.0585 (10) | |
H65A | 0.1236 | 0.2120 | 0.2764 | 0.070* | |
C66 | −0.0485 (5) | 0.0923 (3) | 0.2139 (3) | 0.0544 (9) | |
H66A | −0.0431 | 0.0767 | 0.1549 | 0.065* | |
C71 | −0.0349 (4) | 0.2282 (3) | −0.1360 (2) | 0.0526 (9) | |
H71A | −0.0364 | 0.2429 | −0.0762 | 0.063* | |
C72 | −0.1196 (4) | 0.2561 (3) | −0.1941 (2) | 0.0525 (9) | |
H72A | −0.1771 | 0.2914 | −0.1732 | 0.063* | |
C73 | −0.1204 (4) | 0.2323 (3) | −0.2826 (2) | 0.0545 (9) | |
H73A | −0.1809 | 0.2496 | −0.3227 | 0.065* | |
C74 | −0.0326 (4) | 0.1831 (3) | −0.3126 (3) | 0.0608 (11) | |
H74A | −0.0317 | 0.1681 | −0.3726 | 0.073* | |
C75 | 0.0539 (5) | 0.1561 (3) | −0.2543 (3) | 0.0680 (13) | |
H75A | 0.1138 | 0.1225 | −0.2744 | 0.082* | |
C76 | 0.0522 (4) | 0.1785 (3) | −0.1662 (3) | 0.0644 (13) | |
H76A | 0.1107 | 0.1598 | −0.1266 | 0.077* | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
Au1 | 0.02179 (6) | 0.02859 (6) | 0.03281 (6) | 0.01164 (4) | 0.01219 (4) | 0.01636 (4) |
Fe1 | 0.02462 (18) | 0.03294 (19) | 0.03586 (19) | 0.01371 (15) | 0.01192 (15) | 0.01810 (16) |
C1 | 0.0307 (13) | 0.0436 (16) | 0.0367 (13) | 0.0124 (12) | 0.0113 (11) | 0.0221 (12) |
O1 | 0.0479 (15) | 0.0422 (13) | 0.0493 (14) | 0.0022 (11) | 0.0048 (11) | 0.0167 (11) |
C2 | 0.0340 (14) | 0.0425 (16) | 0.0410 (14) | 0.0166 (12) | 0.0163 (12) | 0.0175 (12) |
O2 | 0.071 (2) | 0.0723 (19) | 0.0415 (13) | 0.0257 (16) | 0.0283 (13) | 0.0255 (13) |
C11 | 0.0187 (10) | 0.0260 (10) | 0.0292 (10) | 0.0112 (8) | 0.0113 (8) | 0.0148 (9) |
N12 | 0.0236 (10) | 0.0276 (10) | 0.0321 (10) | 0.0108 (8) | 0.0135 (8) | 0.0162 (8) |
C13 | 0.0245 (12) | 0.0341 (13) | 0.0433 (14) | 0.0136 (10) | 0.0173 (11) | 0.0193 (11) |
C14 | 0.0273 (12) | 0.0331 (13) | 0.0453 (14) | 0.0175 (10) | 0.0154 (11) | 0.0198 (11) |
N15 | 0.0229 (10) | 0.0237 (9) | 0.0302 (9) | 0.0090 (8) | 0.0116 (8) | 0.0129 (8) |
C21 | 0.074 (3) | 0.0478 (19) | 0.0469 (18) | 0.0110 (18) | 0.0193 (18) | 0.0315 (16) |
C22 | 0.0400 (17) | 0.0452 (18) | 0.074 (2) | 0.0162 (14) | 0.0264 (17) | 0.0375 (18) |
C23 | 0.060 (2) | 0.0309 (15) | 0.060 (2) | 0.0123 (15) | 0.0168 (18) | 0.0181 (15) |
C24 | 0.073 (3) | 0.057 (2) | 0.114 (4) | 0.048 (2) | 0.056 (3) | 0.054 (3) |
C25 | 0.043 (2) | 0.068 (3) | 0.101 (4) | 0.0167 (18) | 0.008 (2) | 0.065 (3) |
C31 | 0.0264 (12) | 0.0290 (12) | 0.0367 (13) | 0.0102 (9) | 0.0160 (10) | 0.0183 (10) |
C32 | 0.0314 (13) | 0.0387 (14) | 0.0387 (13) | 0.0124 (11) | 0.0168 (11) | 0.0221 (12) |
C33 | 0.0455 (18) | 0.0494 (18) | 0.0481 (17) | 0.0157 (14) | 0.0225 (14) | 0.0335 (15) |
C34 | 0.0485 (19) | 0.0425 (17) | 0.065 (2) | 0.0172 (14) | 0.0294 (17) | 0.0367 (16) |
C35 | 0.0446 (17) | 0.0310 (14) | 0.0560 (18) | 0.0124 (12) | 0.0252 (15) | 0.0213 (13) |
C36 | 0.0325 (14) | 0.0318 (13) | 0.0402 (14) | 0.0110 (11) | 0.0179 (11) | 0.0167 (11) |
C37 | 0.0400 (16) | 0.0448 (16) | 0.0327 (13) | 0.0098 (13) | 0.0140 (12) | 0.0176 (12) |
C371 | 0.059 (2) | 0.062 (2) | 0.058 (2) | 0.020 (2) | 0.032 (2) | 0.0134 (19) |
C372 | 0.043 (2) | 0.093 (4) | 0.071 (3) | 0.017 (2) | 0.002 (2) | 0.000 (3) |
C38 | 0.0441 (17) | 0.0308 (14) | 0.0369 (14) | 0.0095 (12) | 0.0132 (12) | 0.0116 (11) |
C381 | 0.043 (2) | 0.059 (2) | 0.056 (2) | 0.0139 (18) | 0.0051 (17) | 0.0143 (19) |
C382 | 0.054 (2) | 0.057 (2) | 0.0395 (16) | 0.0184 (17) | 0.0219 (15) | 0.0164 (15) |
C41 | 0.0270 (12) | 0.0275 (11) | 0.0424 (14) | 0.0125 (9) | 0.0154 (10) | 0.0214 (11) |
C42 | 0.0329 (14) | 0.0297 (13) | 0.0494 (16) | 0.0097 (11) | 0.0167 (12) | 0.0181 (12) |
C43 | 0.0392 (17) | 0.0339 (15) | 0.066 (2) | 0.0044 (13) | 0.0178 (15) | 0.0241 (15) |
C44 | 0.0399 (18) | 0.051 (2) | 0.077 (3) | 0.0094 (15) | 0.0252 (17) | 0.043 (2) |
C45 | 0.0412 (17) | 0.061 (2) | 0.059 (2) | 0.0149 (16) | 0.0247 (15) | 0.0424 (18) |
C46 | 0.0302 (13) | 0.0417 (15) | 0.0429 (14) | 0.0126 (11) | 0.0151 (11) | 0.0271 (13) |
C47 | 0.0467 (19) | 0.0315 (14) | 0.0442 (16) | 0.0030 (13) | 0.0158 (14) | 0.0041 (12) |
C471 | 0.063 (3) | 0.043 (2) | 0.079 (3) | 0.0101 (19) | 0.033 (2) | 0.003 (2) |
C472 | 0.084 (3) | 0.072 (3) | 0.0430 (19) | 0.031 (3) | 0.008 (2) | 0.016 (2) |
C48 | 0.0415 (16) | 0.0520 (18) | 0.0346 (14) | 0.0113 (14) | 0.0150 (12) | 0.0221 (13) |
C481 | 0.076 (3) | 0.057 (2) | 0.058 (2) | 0.027 (2) | 0.014 (2) | 0.015 (2) |
C482 | 0.051 (2) | 0.085 (3) | 0.0443 (19) | 0.019 (2) | 0.0069 (17) | 0.032 (2) |
C51 | 0.049 (3) | 0.224 (11) | 0.082 (4) | 0.002 (5) | 0.011 (3) | 0.063 (6) |
C52 | 0.091 (5) | 0.099 (5) | 0.099 (5) | 0.014 (4) | 0.053 (4) | 0.026 (4) |
C53 | 0.083 (4) | 0.108 (5) | 0.095 (4) | 0.039 (4) | 0.050 (3) | 0.059 (4) |
C54 | 0.075 (3) | 0.100 (4) | 0.076 (3) | 0.024 (3) | 0.041 (3) | 0.052 (3) |
C55 | 0.128 (6) | 0.078 (4) | 0.102 (4) | 0.039 (4) | 0.077 (4) | 0.052 (3) |
C56 | 0.108 (6) | 0.224 (11) | 0.165 (8) | 0.121 (7) | 0.096 (6) | 0.149 (9) |
C61 | 0.081 (3) | 0.0405 (18) | 0.066 (2) | 0.031 (2) | 0.027 (2) | 0.0203 (18) |
C62 | 0.094 (4) | 0.072 (3) | 0.094 (4) | 0.051 (3) | 0.054 (3) | 0.061 (3) |
C63 | 0.109 (5) | 0.118 (5) | 0.048 (2) | 0.077 (4) | 0.030 (3) | 0.044 (3) |
C64 | 0.068 (3) | 0.085 (3) | 0.047 (2) | 0.039 (3) | −0.001 (2) | 0.009 (2) |
C65 | 0.049 (2) | 0.059 (2) | 0.063 (2) | 0.0245 (19) | 0.0138 (19) | 0.022 (2) |
C66 | 0.063 (2) | 0.054 (2) | 0.054 (2) | 0.0317 (19) | 0.0257 (19) | 0.0208 (17) |
C71 | 0.053 (2) | 0.0476 (19) | 0.0440 (17) | 0.0003 (16) | 0.0094 (15) | 0.0212 (15) |
C72 | 0.051 (2) | 0.054 (2) | 0.066 (2) | 0.0251 (17) | 0.0298 (18) | 0.0300 (18) |
C73 | 0.052 (2) | 0.059 (2) | 0.058 (2) | 0.0195 (18) | 0.0157 (17) | 0.0341 (19) |
C74 | 0.080 (3) | 0.0412 (19) | 0.057 (2) | 0.0080 (19) | 0.037 (2) | 0.0164 (17) |
C75 | 0.068 (3) | 0.046 (2) | 0.115 (4) | 0.029 (2) | 0.054 (3) | 0.041 (2) |
C76 | 0.0404 (19) | 0.062 (2) | 0.097 (3) | 0.0135 (18) | 0.010 (2) | 0.053 (3) |
Geometric parameters (Å, º) top
Au1—C11 | 2.019 (2) | C42—C47 | 1.522 (5) |
Au1—Fe1 | 2.5093 (4) | C43—C44 | 1.378 (6) |
Fe1—C2 | 1.732 (3) | C43—H43A | 0.9500 |
Fe1—C1 | 1.741 (3) | C44—C45 | 1.381 (6) |
Fe1—C21 | 2.085 (4) | C44—H44A | 0.9500 |
Fe1—C24 | 2.084 (4) | C45—C46 | 1.393 (4) |
Fe1—C23 | 2.085 (4) | C45—H45A | 0.9500 |
Fe1—C25 | 2.090 (3) | C46—C48 | 1.521 (5) |
Fe1—C22 | 2.111 (4) | C47—C471 | 1.517 (5) |
C1—O1 | 1.154 (4) | C47—C472 | 1.533 (6) |
C2—O2 | 1.161 (4) | C47—H47A | 1.0000 |
C11—N15 | 1.336 (3) | C471—H47B | 0.9800 |
C11—N12 | 1.366 (3) | C471—H47C | 0.9800 |
N12—C13 | 1.385 (3) | C471—H47D | 0.9800 |
N12—C31 | 1.439 (3) | C472—H47E | 0.9800 |
C13—C14 | 1.348 (4) | C472—H47F | 0.9800 |
C13—H13A | 0.9500 | C472—H47G | 0.9800 |
C14—N15 | 1.383 (3) | C48—C481 | 1.517 (6) |
C14—H14A | 0.9500 | C48—C482 | 1.530 (5) |
N15—C41 | 1.448 (3) | C48—H48A | 1.0000 |
C21—C22 | 1.407 (6) | C481—H48B | 0.9800 |
C21—C25 | 1.413 (7) | C481—H48C | 0.9800 |
C21—H21A | 1.0000 | C481—H48D | 0.9800 |
C22—C23 | 1.398 (6) | C482—H48E | 0.9800 |
C22—H22A | 1.0000 | C482—H48F | 0.9800 |
C23—C24 | 1.414 (7) | C482—H48G | 0.9800 |
C23—H23A | 1.0000 | C51—C52 | 1.399 (2) |
C24—C25 | 1.375 (8) | C51—C56 | 1.400 (2) |
C24—H24A | 1.0000 | C51—H51A | 0.9500 |
C25—H25A | 1.0000 | C52—C53 | 1.394 (2) |
C31—C32 | 1.398 (4) | C52—H52A | 0.9500 |
C31—C36 | 1.392 (4) | C53—C54 | 1.393 (2) |
C32—C33 | 1.401 (4) | C53—H53A | 0.9500 |
C32—C37 | 1.512 (5) | C54—C55 | 1.394 (2) |
C33—C34 | 1.381 (6) | C54—H54A | 0.9500 |
C33—H33A | 0.9500 | C55—C56 | 1.397 (2) |
C34—C35 | 1.381 (5) | C55—H55A | 0.9500 |
C34—H34A | 0.9500 | C56—H56A | 0.9500 |
C35—C36 | 1.398 (4) | C61—C66 | 1.368 (7) |
C35—H35A | 0.9500 | C61—C62 | 1.374 (7) |
C36—C38 | 1.522 (4) | C61—H61A | 0.9500 |
C37—C372 | 1.518 (6) | C62—C63 | 1.398 (9) |
C37—C371 | 1.519 (5) | C62—H62A | 0.9500 |
C37—H37A | 1.0000 | C63—C64 | 1.376 (9) |
C371—H37B | 0.9800 | C63—H63A | 0.9500 |
C371—H37C | 0.9800 | C64—C65 | 1.362 (7) |
C371—H37D | 0.9800 | C64—H64A | 0.9500 |
C372—H37E | 0.9800 | C65—C66 | 1.365 (6) |
C372—H37F | 0.9800 | C65—H65A | 0.9500 |
C372—H37G | 0.9800 | C66—H66A | 0.9500 |
C38—C382 | 1.521 (5) | C71—C76 | 1.3937 (19) |
C38—C381 | 1.540 (5) | C71—C72 | 1.3930 (19) |
C38—H38A | 1.0000 | C71—H71A | 0.9500 |
C381—H38B | 0.9800 | C72—C73 | 1.3925 (19) |
C381—H38C | 0.9800 | C72—H72A | 0.9500 |
C381—H38D | 0.9800 | C73—C74 | 1.3941 (19) |
C382—H38E | 0.9800 | C73—H73A | 0.9500 |
C382—H38F | 0.9800 | C74—C75 | 1.3943 (19) |
C382—H38G | 0.9800 | C74—H74A | 0.9500 |
C41—C42 | 1.395 (4) | C75—C76 | 1.394 (2) |
C41—C46 | 1.400 (4) | C75—H75A | 0.9500 |
C42—C43 | 1.396 (4) | C76—H76A | 0.9500 |
| | | |
C11—Au1—Fe1 | 171.02 (7) | C38—C381—H38C | 109.5 |
C2—Fe1—C1 | 94.57 (15) | H38B—C381—H38C | 109.5 |
C2—Fe1—C21 | 163.94 (16) | C38—C381—H38D | 109.5 |
C1—Fe1—C21 | 101.24 (15) | H38B—C381—H38D | 109.5 |
C2—Fe1—C24 | 101.16 (19) | H38C—C381—H38D | 109.5 |
C1—Fe1—C24 | 134.74 (19) | C38—C382—H38E | 109.5 |
C21—Fe1—C24 | 65.5 (2) | C38—C382—H38F | 109.5 |
C2—Fe1—C23 | 98.61 (17) | H38E—C382—H38F | 109.5 |
C1—Fe1—C23 | 166.59 (16) | C38—C382—H38G | 109.5 |
C21—Fe1—C23 | 65.49 (17) | H38E—C382—H38G | 109.5 |
C24—Fe1—C23 | 39.64 (19) | H38F—C382—H38G | 109.5 |
C2—Fe1—C25 | 133.4 (2) | C42—C41—C46 | 122.6 (3) |
C1—Fe1—C25 | 103.28 (17) | C42—C41—N15 | 119.0 (3) |
C21—Fe1—C25 | 39.6 (2) | C46—C41—N15 | 118.4 (3) |
C24—Fe1—C25 | 38.5 (2) | C41—C42—C43 | 117.6 (3) |
C23—Fe1—C25 | 65.60 (18) | C41—C42—C47 | 121.9 (3) |
C2—Fe1—C22 | 128.57 (16) | C43—C42—C47 | 120.5 (3) |
C1—Fe1—C22 | 130.97 (16) | C44—C43—C42 | 120.9 (3) |
C21—Fe1—C22 | 39.17 (16) | C44—C43—H43A | 119.5 |
C24—Fe1—C22 | 65.79 (17) | C42—C43—H43A | 119.5 |
C23—Fe1—C22 | 38.91 (17) | C43—C44—C45 | 120.4 (3) |
C25—Fe1—C22 | 65.94 (16) | C43—C44—H44A | 119.8 |
C2—Fe1—Au1 | 82.17 (11) | C45—C44—H44A | 119.8 |
C1—Fe1—Au1 | 78.48 (10) | C44—C45—C46 | 121.0 (3) |
C21—Fe1—Au1 | 103.67 (14) | C44—C45—H45A | 119.5 |
C24—Fe1—Au1 | 145.31 (15) | C46—C45—H45A | 119.5 |
C23—Fe1—Au1 | 105.68 (12) | C45—C46—C41 | 117.4 (3) |
C25—Fe1—Au1 | 143.20 (17) | C45—C46—C48 | 120.3 (3) |
C22—Fe1—Au1 | 84.98 (10) | C41—C46—C48 | 122.3 (3) |
O1—C1—Fe1 | 177.2 (3) | C471—C47—C42 | 113.0 (4) |
O2—C2—Fe1 | 176.9 (3) | C471—C47—C472 | 110.7 (4) |
N15—C11—N12 | 103.9 (2) | C42—C47—C472 | 109.3 (3) |
N15—C11—Au1 | 132.60 (19) | C471—C47—H47A | 107.9 |
N12—C11—Au1 | 123.47 (17) | C42—C47—H47A | 107.9 |
C11—N12—C13 | 111.3 (2) | C472—C47—H47A | 107.9 |
C11—N12—C31 | 124.2 (2) | C47—C471—H47B | 109.5 |
C13—N12—C31 | 124.5 (2) | C47—C471—H47C | 109.5 |
C14—C13—N12 | 106.2 (2) | H47B—C471—H47C | 109.5 |
C14—C13—H13A | 126.9 | C47—C471—H47D | 109.5 |
N12—C13—H13A | 126.9 | H47B—C471—H47D | 109.5 |
C13—C14—N15 | 106.6 (2) | H47C—C471—H47D | 109.5 |
C13—C14—H14A | 126.7 | C47—C472—H47E | 109.5 |
N15—C14—H14A | 126.7 | C47—C472—H47F | 109.5 |
C11—N15—C14 | 112.0 (2) | H47E—C472—H47F | 109.5 |
C11—N15—C41 | 124.9 (2) | C47—C472—H47G | 109.5 |
C14—N15—C41 | 123.1 (2) | H47E—C472—H47G | 109.5 |
C22—C21—C25 | 108.3 (4) | H47F—C472—H47G | 109.5 |
C22—C21—Fe1 | 71.4 (2) | C481—C48—C46 | 110.7 (3) |
C25—C21—Fe1 | 70.4 (2) | C481—C48—C482 | 110.6 (3) |
C22—C21—H21A | 125.8 | C46—C48—C482 | 111.6 (3) |
C25—C21—H21A | 125.8 | C481—C48—H48A | 107.9 |
Fe1—C21—H21A | 125.8 | C46—C48—H48A | 107.9 |
C23—C22—C21 | 107.1 (4) | C482—C48—H48A | 107.9 |
C23—C22—Fe1 | 69.5 (2) | C48—C481—H48B | 109.5 |
C21—C22—Fe1 | 69.4 (2) | C48—C481—H48C | 109.5 |
C23—C22—H22A | 126.5 | H48B—C481—H48C | 109.5 |
C21—C22—H22A | 126.5 | C48—C481—H48D | 109.5 |
Fe1—C22—H22A | 126.5 | H48B—C481—H48D | 109.5 |
C22—C23—C24 | 108.3 (4) | H48C—C481—H48D | 109.5 |
C22—C23—Fe1 | 71.5 (2) | C48—C482—H48E | 109.5 |
C24—C23—Fe1 | 70.2 (2) | C48—C482—H48F | 109.5 |
C22—C23—H23A | 125.8 | H48E—C482—H48F | 109.5 |
C24—C23—H23A | 125.8 | C48—C482—H48G | 109.5 |
Fe1—C23—H23A | 125.8 | H48E—C482—H48G | 109.5 |
C25—C24—C23 | 108.4 (4) | H48F—C482—H48G | 109.5 |
C25—C24—Fe1 | 71.0 (2) | C52—C51—C56 | 119.9 (6) |
C23—C24—Fe1 | 70.2 (2) | C52—C51—H51A | 120.0 |
C25—C24—H24A | 125.8 | C56—C51—H51A | 120.0 |
C23—C24—H24A | 125.8 | C53—C52—C51 | 120.0 (6) |
Fe1—C24—H24A | 125.8 | C53—C52—H52A | 120.0 |
C24—C25—C21 | 107.9 (4) | C51—C52—H52A | 120.0 |
C24—C25—Fe1 | 70.5 (2) | C54—C53—C52 | 119.7 (6) |
C21—C25—Fe1 | 70.0 (2) | C54—C53—H53A | 120.1 |
C24—C25—H25A | 126.0 | C52—C53—H53A | 120.1 |
C21—C25—H25A | 126.0 | C53—C54—C55 | 120.7 (6) |
Fe1—C25—H25A | 126.0 | C53—C54—H54A | 119.6 |
C32—C31—C36 | 123.7 (3) | C55—C54—H54A | 119.6 |
C32—C31—N12 | 118.2 (3) | C54—C55—C56 | 119.5 (6) |
C36—C31—N12 | 118.1 (2) | C54—C55—H55A | 120.3 |
C31—C32—C33 | 116.8 (3) | C56—C55—H55A | 120.3 |
C31—C32—C37 | 122.4 (3) | C55—C56—C51 | 120.0 (6) |
C33—C32—C37 | 120.8 (3) | C55—C56—H56A | 120.0 |
C34—C33—C32 | 120.9 (3) | C51—C56—H56A | 120.0 |
C34—C33—H33A | 119.5 | C66—C61—C62 | 121.0 (5) |
C32—C33—H33A | 119.5 | C66—C61—H61A | 119.5 |
C35—C34—C33 | 120.6 (3) | C62—C61—H61A | 119.5 |
C35—C34—H34A | 119.7 | C61—C62—C63 | 118.1 (5) |
C33—C34—H34A | 119.7 | C61—C62—H62A | 121.0 |
C34—C35—C36 | 121.0 (3) | C63—C62—H62A | 121.0 |
C34—C35—H35A | 119.5 | C64—C63—C62 | 120.7 (5) |
C36—C35—H35A | 119.5 | C64—C63—H63A | 119.7 |
C31—C36—C35 | 117.1 (3) | C62—C63—H63A | 119.7 |
C31—C36—C38 | 122.5 (3) | C65—C64—C63 | 119.5 (5) |
C35—C36—C38 | 120.4 (3) | C65—C64—H64A | 120.3 |
C32—C37—C372 | 111.2 (4) | C63—C64—H64A | 120.3 |
C32—C37—C371 | 111.6 (3) | C66—C65—C64 | 120.7 (5) |
C372—C37—C371 | 110.8 (4) | C66—C65—H65A | 119.6 |
C32—C37—H37A | 107.7 | C64—C65—H65A | 119.6 |
C372—C37—H37A | 107.7 | C65—C66—C61 | 120.1 (4) |
C371—C37—H37A | 107.7 | C65—C66—H66A | 120.0 |
C37—C371—H37B | 109.5 | C61—C66—H66A | 120.0 |
C37—C371—H37C | 109.5 | C76—C71—C72 | 119.6 (3) |
H37B—C371—H37C | 109.5 | C76—C71—H71A | 120.2 |
C37—C371—H37D | 109.5 | C72—C71—H71A | 120.2 |
H37B—C371—H37D | 109.5 | C73—C72—C71 | 120.2 (3) |
H37C—C371—H37D | 109.5 | C73—C72—H72A | 119.9 |
C37—C372—H37E | 109.5 | C71—C72—H72A | 119.9 |
C37—C372—H37F | 109.5 | C72—C73—C74 | 120.1 (3) |
H37E—C372—H37F | 109.5 | C72—C73—H73A | 119.9 |
C37—C372—H37G | 109.5 | C74—C73—H73A | 119.9 |
H37E—C372—H37G | 109.5 | C75—C74—C73 | 119.9 (4) |
H37F—C372—H37G | 109.5 | C75—C74—H74A | 120.1 |
C36—C38—C382 | 110.5 (3) | C73—C74—H74A | 120.1 |
C36—C38—C381 | 111.8 (3) | C76—C75—C74 | 119.8 (4) |
C382—C38—C381 | 111.5 (3) | C76—C75—H75A | 120.1 |
C36—C38—H38A | 107.6 | C74—C75—H75A | 120.1 |
C382—C38—H38A | 107.6 | C75—C76—C71 | 120.4 (3) |
C381—C38—H38A | 107.6 | C75—C76—H76A | 119.8 |
C38—C381—H38B | 109.5 | C71—C76—H76A | 119.8 |
| | | |
N15—C11—N12—C13 | −0.3 (3) | C33—C32—C37—C371 | 59.0 (5) |
Au1—C11—N12—C13 | 179.75 (19) | C31—C36—C38—C382 | −111.0 (3) |
N15—C11—N12—C31 | −177.9 (2) | C35—C36—C38—C382 | 65.9 (4) |
Au1—C11—N12—C31 | 2.2 (4) | C31—C36—C38—C381 | 124.2 (3) |
C11—N12—C13—C14 | 0.3 (3) | C35—C36—C38—C381 | −58.9 (4) |
C31—N12—C13—C14 | 177.8 (3) | C11—N15—C41—C42 | 90.2 (3) |
N12—C13—C14—N15 | −0.1 (3) | C14—N15—C41—C42 | −90.2 (3) |
N12—C11—N15—C14 | 0.3 (3) | C11—N15—C41—C46 | −90.7 (3) |
Au1—C11—N15—C14 | −179.8 (2) | C14—N15—C41—C46 | 88.9 (3) |
N12—C11—N15—C41 | 180.0 (2) | C46—C41—C42—C43 | 0.2 (5) |
Au1—C11—N15—C41 | −0.1 (4) | N15—C41—C42—C43 | 179.3 (3) |
C13—C14—N15—C11 | −0.1 (3) | C46—C41—C42—C47 | 177.7 (3) |
C13—C14—N15—C41 | −179.8 (3) | N15—C41—C42—C47 | −3.2 (4) |
C25—C21—C22—C23 | 1.4 (4) | C41—C42—C43—C44 | 0.2 (5) |
Fe1—C21—C22—C23 | −59.6 (3) | C47—C42—C43—C44 | −177.4 (4) |
C25—C21—C22—Fe1 | 61.1 (3) | C42—C43—C44—C45 | −0.2 (6) |
C21—C22—C23—C24 | −1.3 (4) | C43—C44—C45—C46 | −0.1 (6) |
Fe1—C22—C23—C24 | −60.9 (3) | C44—C45—C46—C41 | 0.4 (5) |
C21—C22—C23—Fe1 | 59.5 (2) | C44—C45—C46—C48 | 178.5 (3) |
C22—C23—C24—C25 | 0.7 (5) | C42—C41—C46—C45 | −0.5 (5) |
Fe1—C23—C24—C25 | −61.0 (3) | N15—C41—C46—C45 | −179.6 (3) |
C22—C23—C24—Fe1 | 61.7 (3) | C42—C41—C46—C48 | −178.5 (3) |
C23—C24—C25—C21 | 0.2 (5) | N15—C41—C46—C48 | 2.4 (4) |
Fe1—C24—C25—C21 | −60.3 (3) | C41—C42—C47—C471 | 134.5 (4) |
C23—C24—C25—Fe1 | 60.5 (3) | C43—C42—C47—C471 | −48.0 (5) |
C22—C21—C25—C24 | −1.0 (4) | C41—C42—C47—C472 | −101.7 (4) |
Fe1—C21—C25—C24 | 60.7 (3) | C43—C42—C47—C472 | 75.8 (4) |
C22—C21—C25—Fe1 | −61.7 (3) | C45—C46—C48—C481 | −74.1 (4) |
C11—N12—C31—C32 | −92.5 (3) | C41—C46—C48—C481 | 103.8 (4) |
C13—N12—C31—C32 | 90.2 (3) | C45—C46—C48—C482 | 49.5 (5) |
C11—N12—C31—C36 | 88.1 (3) | C41—C46—C48—C482 | −132.5 (3) |
C13—N12—C31—C36 | −89.2 (3) | C56—C51—C52—C53 | 2.8 (11) |
C36—C31—C32—C33 | −0.2 (5) | C51—C52—C53—C54 | −0.9 (10) |
N12—C31—C32—C33 | −179.5 (3) | C52—C53—C54—C55 | −2.0 (9) |
C36—C31—C32—C37 | −179.5 (3) | C53—C54—C55—C56 | 3.1 (8) |
N12—C31—C32—C37 | 1.2 (4) | C54—C55—C56—C51 | −1.1 (10) |
C31—C32—C33—C34 | 0.7 (5) | C52—C51—C56—C55 | −1.8 (12) |
C37—C32—C33—C34 | −180.0 (3) | C66—C61—C62—C63 | 0.7 (7) |
C32—C33—C34—C35 | −1.1 (6) | C61—C62—C63—C64 | −0.3 (7) |
C33—C34—C35—C36 | 1.0 (6) | C62—C63—C64—C65 | −0.2 (8) |
C32—C31—C36—C35 | 0.1 (5) | C63—C64—C65—C66 | 0.3 (7) |
N12—C31—C36—C35 | 179.4 (3) | C64—C65—C66—C61 | 0.0 (7) |
C32—C31—C36—C38 | 177.1 (3) | C62—C61—C66—C65 | −0.6 (7) |
N12—C31—C36—C38 | −3.6 (4) | C76—C71—C72—C73 | 1.7 (6) |
C34—C35—C36—C31 | −0.5 (5) | C71—C72—C73—C74 | −2.1 (6) |
C34—C35—C36—C38 | −177.5 (3) | C72—C73—C74—C75 | 1.3 (7) |
C31—C32—C37—C372 | 114.1 (4) | C73—C74—C75—C76 | −0.1 (7) |
C33—C32—C37—C372 | −65.2 (5) | C74—C75—C76—C71 | −0.3 (7) |
C31—C32—C37—C371 | −121.7 (4) | C72—C71—C76—C75 | −0.5 (6) |
Hydrogen-bond geometry (Å, º) topCg(C51) and Cg(C61) are the centroids of the C51–C56
and C61–C66 benzene solvent molecules. |
D—H···A | D—H | H···A | D···A | D—H···A |
C14—H14A···Cg(C61)i | 0.95 | 2.74 | 3.37 | 158 |
C62—H62A···Cg(C51)ii | 0.95 | 3.00 | 3.88 | 155 |
C45—H45A···Cg(C51) | 0.95 | 3.12 | 4.03 | 162 |
Symmetry codes: (i) x+1, y, z; (ii) −x, −y, −z+1. |
Structural characteristics of (I) in comparison to those of (II)
(Fructos et al., 2005), (Me3P)AuCl (Angermaier et al.,
1994),
(F3P)AuCl (Schödel et al., 2006) and (OC)AuCl (Jones,
1982).
Fp is ????. topE | X | Compound | E—Au—X (°) | Au—Au (Å) | E—Au (Å) |
C | Fp | (NHC)AuFp, (I) | 171.02 (7) | 8.6341 (5) | 2.019 (2) |
C | Cl | (NHC)AuCl, (II) | 177.1 | 8.327 | 1.941 |
P | Fp | (Me3P)AuCl* | 178.4 | 3.338 | 2.234 |
P | Fp | (F3P)AuCl | 173.6 | 3.350 | 2.172 |
C | Cl | (OC)AuCl | 180.0 | 3.380 | 1.926 |
Note: (*) since this structure has three molecules in the asymmetric unit, mean
values were calculated. |