metal-organic compounds
[μ-1,1′-Bis(diphenylphosphino)ferrocene-κ2P:P′]bis{[(Z)-O-isopropyl-N-(4-methylphenyl)thiocarbamato-κS]gold(I)}
aDepartment of Chemistry, National University of Singapore, Singapore 117543, and bDepartment of Chemistry, University of Malaya, 50603 Kuala Lumpur, Malaysia
*Correspondence e-mail: edward.tiekink@gmail.com
In the title compound, [Au2Fe(C11H14NOS)2(C17H14P)2], the FeII atom is located on a crystallographic centre of inversion. For the AuI atom, the deviation from linearity defined by its S,P-donor set [S—Au—P = 178.17 (8) Å] is due to an intramolecular Au⋯O contact [3.079 (4) Å]. In the crystal, supramolecular chains mediated by C—H⋯N interactions are formed, which run parallel to [001].
Related literature
For structural systematics and luminescence properties of phosphinegold(I) carbonimidothioates, see: Ho et al. (2006); Ho & Tiekink (2007); Kuan et al. (2008). For the synthesis, see Hall et al. (1993). For a related structure, see Ho & Tiekink (2009).
Experimental
Crystal data
|
Refinement
|
|
Data collection: SMART (Bruker, 2000); cell SAINT (Bruker, 2000); data reduction: SAINT; program(s) used to solve structure: PATTY in DIRDIF92 (Beurskens et al., 1992); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: DIAMOND (Brandenburg, 2006); software used to prepare material for publication: publCIF (Westrip, 2009).
Supporting information
10.1107/S1600536809047898/hb5221sup1.cif
contains datablocks global, I. DOI:Structure factors: contains datablock I. DOI: 10.1107/S1600536809047898/hb5221Isup2.hkl
Compound (I) was prepared following the standard literature procedure from the reaction of dppf(AuCl)2 and (iPr)OC(S)N(H)C6H4Me-p in the presence of base (Hall et al., 1993).
The H atoms were geometrically placed (C—H = 0.94–0.99 Å) and refined as riding with Uiso(H) = 1.2–1.5Ueq(C). The maximum and minimum residual electron density peaks of 1.74 and 0.93 e Å-3, respectively, were located 1.03 Å and 1.02 Å from the Au atom.
Data collection: SMART (Bruker, 2000); cell
SAINT (Bruker, 2000); data reduction: SAINT (Bruker, 2000); program(s) used to solve structure: PATTY in DIRDIF92 (Beurskens et al., 1992); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: DIAMOND (Brandenburg, 2006); software used to prepare material for publication: publCIF (Westrip, 2009).[Au2Fe(C11H14NOS)2(C17H14P)2] | Z = 1 |
Mr = 1364.87 | F(000) = 668 |
Triclinic, P1 | Dx = 1.710 Mg m−3 |
Hall symbol: -P 1 | Mo Kα radiation, λ = 0.71069 Å |
a = 8.1631 (9) Å | Cell parameters from 2346 reflections |
b = 13.4959 (14) Å | θ = 2.7–30.0° |
c = 13.5154 (14) Å | µ = 5.97 mm−1 |
α = 107.440 (2)° | T = 223 K |
β = 97.401 (2)° | Block, orange |
γ = 106.366 (2)° | 0.21 × 0.07 × 0.04 mm |
V = 1325.5 (2) Å3 |
Bruker SMART CCD diffractometer | 4651 independent reflections |
Radiation source: fine-focus sealed tube | 3790 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.036 |
ω scans | θmax = 25.0°, θmin = 1.6° |
Absorption correction: multi-scan (SADABS; Bruker, 2000) | h = −9→5 |
Tmin = 0.629, Tmax = 1 | k = −16→15 |
7710 measured reflections | l = −15→16 |
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)] = 0.040 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.088 | H-atom parameters constrained |
S = 0.98 | w = 1/[σ2(Fo2) + (0.0429P)2] where P = (Fo2 + 2Fc2)/3 |
4651 reflections | (Δ/σ)max < 0.001 |
305 parameters | Δρmax = 1.74 e Å−3 |
0 restraints | Δρmin = −0.93 e Å−3 |
[Au2Fe(C11H14NOS)2(C17H14P)2] | γ = 106.366 (2)° |
Mr = 1364.87 | V = 1325.5 (2) Å3 |
Triclinic, P1 | Z = 1 |
a = 8.1631 (9) Å | Mo Kα radiation |
b = 13.4959 (14) Å | µ = 5.97 mm−1 |
c = 13.5154 (14) Å | T = 223 K |
α = 107.440 (2)° | 0.21 × 0.07 × 0.04 mm |
β = 97.401 (2)° |
Bruker SMART CCD diffractometer | 4651 independent reflections |
Absorption correction: multi-scan (SADABS; Bruker, 2000) | 3790 reflections with I > 2σ(I) |
Tmin = 0.629, Tmax = 1 | Rint = 0.036 |
7710 measured reflections |
R[F2 > 2σ(F2)] = 0.040 | 0 restraints |
wR(F2) = 0.088 | H-atom parameters constrained |
S = 0.98 | Δρmax = 1.74 e Å−3 |
4651 reflections | Δρmin = −0.93 e Å−3 |
305 parameters |
Geometry. All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell s.u.'s are taken into account individually in the estimation of s.u.'s in distances, angles and torsion angles; correlations between s.u.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell s.u.'s is used for estimating s.u.'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 > 2σ(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 | ||
Au | 0.13463 (4) | 0.49437 (2) | 0.20439 (2) | 0.03125 (11) | |
Fe | 0.5000 | 0.5000 | 0.0000 | 0.0270 (3) | |
S1 | 0.1355 (3) | 0.63009 (17) | 0.35458 (14) | 0.0434 (5) | |
P1 | 0.1284 (2) | 0.35677 (14) | 0.05834 (13) | 0.0266 (4) | |
O1 | 0.4456 (6) | 0.6118 (4) | 0.4008 (3) | 0.0351 (11) | |
N1 | 0.3945 (9) | 0.7445 (5) | 0.5308 (5) | 0.0457 (17) | |
C1 | 0.3418 (10) | 0.6707 (6) | 0.4401 (6) | 0.0382 (18) | |
C2 | 0.2892 (11) | 0.8073 (7) | 0.5704 (6) | 0.046 (2) | |
C3 | 0.2959 (12) | 0.8999 (7) | 0.5460 (7) | 0.057 (2) | |
H3 | 0.3647 | 0.9185 | 0.4993 | 0.069* | |
C4 | 0.2016 (12) | 0.9663 (7) | 0.5898 (7) | 0.059 (2) | |
H4 | 0.2036 | 1.0270 | 0.5689 | 0.071* | |
C5 | 0.1061 (12) | 0.9464 (8) | 0.6622 (6) | 0.056 (2) | |
C6 | 0.1049 (13) | 0.8551 (9) | 0.6871 (6) | 0.062 (3) | |
H6 | 0.0406 | 0.8381 | 0.7363 | 0.075* | |
C7 | 0.1941 (12) | 0.7875 (8) | 0.6427 (7) | 0.056 (2) | |
H7 | 0.1897 | 0.7259 | 0.6625 | 0.068* | |
C8 | 0.0014 (15) | 1.0160 (9) | 0.7055 (8) | 0.087 (4) | |
H8A | −0.1098 | 0.9924 | 0.6548 | 0.130* | |
H8B | 0.0657 | 1.0926 | 0.7178 | 0.130* | |
H8C | −0.0201 | 1.0084 | 0.7723 | 0.130* | |
C9 | 0.6271 (10) | 0.6486 (7) | 0.4650 (6) | 0.046 (2) | |
H9 | 0.6256 | 0.6677 | 0.5414 | 0.055* | |
C10 | 0.6848 (11) | 0.5484 (7) | 0.4295 (6) | 0.047 (2) | |
H10A | 0.6075 | 0.4880 | 0.4441 | 0.071* | |
H10B | 0.8042 | 0.5666 | 0.4682 | 0.071* | |
H10C | 0.6794 | 0.5267 | 0.3536 | 0.071* | |
C11 | 0.7391 (11) | 0.7471 (7) | 0.4477 (7) | 0.060 (2) | |
H11A | 0.6955 | 0.8079 | 0.4726 | 0.091* | |
H11B | 0.7357 | 0.7298 | 0.3723 | 0.091* | |
H11C | 0.8590 | 0.7680 | 0.4870 | 0.091* | |
C12 | 0.2458 (8) | 0.4006 (5) | −0.0322 (5) | 0.0263 (15) | |
C13 | 0.2562 (9) | 0.5014 (6) | −0.0501 (5) | 0.0329 (16) | |
H13 | 0.2079 | 0.5535 | −0.0145 | 0.039* | |
C14 | 0.3500 (10) | 0.5101 (7) | −0.1288 (6) | 0.044 (2) | |
H14 | 0.3747 | 0.5680 | −0.1558 | 0.053* | |
C15 | 0.4004 (10) | 0.4153 (7) | −0.1600 (5) | 0.045 (2) | |
H15 | 0.4655 | 0.3996 | −0.2116 | 0.054* | |
C16 | 0.3375 (9) | 0.3480 (6) | −0.1013 (5) | 0.0354 (17) | |
H16 | 0.3534 | 0.2804 | −0.1070 | 0.043* | |
C17 | −0.0903 (8) | 0.2718 (5) | −0.0236 (5) | 0.0267 (15) | |
C18 | −0.2168 (10) | 0.2284 (6) | 0.0247 (6) | 0.0423 (19) | |
H18 | −0.1893 | 0.2431 | 0.0985 | 0.051* | |
C19 | −0.3841 (11) | 0.1631 (7) | −0.0356 (8) | 0.058 (2) | |
H19 | −0.4695 | 0.1317 | −0.0030 | 0.070* | |
C20 | −0.4260 (11) | 0.1439 (7) | −0.1435 (8) | 0.057 (2) | |
H20 | −0.5399 | 0.0997 | −0.1843 | 0.068* | |
C21 | −0.3025 (11) | 0.1890 (6) | −0.1906 (7) | 0.049 (2) | |
H21 | −0.3323 | 0.1767 | −0.2638 | 0.059* | |
C22 | −0.1347 (10) | 0.2522 (6) | −0.1327 (6) | 0.0384 (18) | |
H22 | −0.0499 | 0.2822 | −0.1663 | 0.046* | |
C23 | 0.2152 (8) | 0.2599 (5) | 0.0958 (5) | 0.0294 (15) | |
C24 | 0.3196 (10) | 0.2918 (7) | 0.1944 (6) | 0.0423 (19) | |
H24 | 0.3507 | 0.3648 | 0.2416 | 0.051* | |
C25 | 0.3806 (12) | 0.2174 (8) | 0.2258 (7) | 0.059 (2) | |
H25 | 0.4512 | 0.2398 | 0.2946 | 0.070* | |
C26 | 0.3391 (12) | 0.1131 (8) | 0.1582 (7) | 0.056 (2) | |
H26 | 0.3840 | 0.0639 | 0.1797 | 0.067* | |
C27 | 0.2318 (10) | 0.0772 (6) | 0.0580 (7) | 0.048 (2) | |
H27 | 0.2006 | 0.0036 | 0.0119 | 0.057* | |
C28 | 0.1709 (9) | 0.1516 (6) | 0.0263 (6) | 0.0400 (18) | |
H28 | 0.0993 | 0.1289 | −0.0422 | 0.048* |
U11 | U22 | U33 | U12 | U13 | U23 | |
Au | 0.02798 (16) | 0.03521 (17) | 0.02566 (15) | 0.00940 (12) | 0.00453 (10) | 0.00587 (11) |
Fe | 0.0229 (7) | 0.0322 (8) | 0.0227 (6) | 0.0055 (6) | 0.0028 (5) | 0.0098 (6) |
S1 | 0.0352 (11) | 0.0527 (12) | 0.0320 (9) | 0.0184 (10) | 0.0026 (8) | −0.0004 (9) |
P1 | 0.0224 (9) | 0.0272 (9) | 0.0276 (9) | 0.0064 (8) | 0.0042 (7) | 0.0086 (8) |
O1 | 0.028 (3) | 0.042 (3) | 0.029 (2) | 0.014 (2) | 0.000 (2) | 0.005 (2) |
N1 | 0.046 (4) | 0.048 (4) | 0.033 (3) | 0.020 (3) | −0.002 (3) | 0.003 (3) |
C1 | 0.040 (4) | 0.035 (4) | 0.033 (4) | 0.003 (4) | 0.003 (3) | 0.015 (4) |
C2 | 0.048 (5) | 0.054 (5) | 0.025 (4) | 0.019 (4) | 0.000 (4) | 0.003 (4) |
C3 | 0.064 (6) | 0.051 (5) | 0.056 (5) | 0.016 (5) | 0.028 (5) | 0.016 (5) |
C4 | 0.065 (6) | 0.040 (5) | 0.063 (6) | 0.016 (5) | 0.013 (5) | 0.008 (4) |
C5 | 0.054 (6) | 0.068 (6) | 0.027 (4) | 0.018 (5) | −0.002 (4) | −0.005 (4) |
C6 | 0.063 (6) | 0.092 (8) | 0.034 (4) | 0.027 (6) | 0.015 (4) | 0.023 (5) |
C7 | 0.053 (5) | 0.075 (6) | 0.050 (5) | 0.032 (5) | 0.005 (4) | 0.028 (5) |
C8 | 0.086 (8) | 0.099 (8) | 0.053 (6) | 0.048 (7) | 0.003 (6) | −0.015 (6) |
C9 | 0.036 (4) | 0.058 (5) | 0.031 (4) | 0.008 (4) | −0.002 (3) | 0.011 (4) |
C10 | 0.044 (5) | 0.070 (6) | 0.034 (4) | 0.027 (4) | 0.007 (4) | 0.021 (4) |
C11 | 0.043 (5) | 0.051 (5) | 0.064 (6) | −0.001 (4) | −0.001 (4) | 0.009 (5) |
C12 | 0.023 (3) | 0.025 (3) | 0.027 (3) | 0.006 (3) | 0.001 (3) | 0.007 (3) |
C13 | 0.025 (4) | 0.037 (4) | 0.035 (4) | 0.010 (3) | −0.002 (3) | 0.016 (3) |
C14 | 0.043 (5) | 0.055 (5) | 0.032 (4) | 0.007 (4) | −0.002 (4) | 0.023 (4) |
C15 | 0.037 (4) | 0.064 (6) | 0.018 (3) | 0.002 (4) | 0.005 (3) | 0.007 (4) |
C16 | 0.032 (4) | 0.037 (4) | 0.030 (4) | 0.009 (3) | 0.005 (3) | 0.006 (3) |
C17 | 0.026 (4) | 0.016 (3) | 0.037 (4) | 0.007 (3) | 0.003 (3) | 0.009 (3) |
C18 | 0.036 (4) | 0.044 (5) | 0.053 (5) | 0.014 (4) | 0.019 (4) | 0.022 (4) |
C19 | 0.036 (5) | 0.044 (5) | 0.104 (8) | 0.011 (4) | 0.029 (5) | 0.035 (5) |
C20 | 0.025 (4) | 0.042 (5) | 0.088 (7) | 0.006 (4) | −0.009 (5) | 0.016 (5) |
C21 | 0.036 (5) | 0.045 (5) | 0.049 (5) | 0.009 (4) | −0.011 (4) | 0.006 (4) |
C22 | 0.036 (4) | 0.038 (4) | 0.037 (4) | 0.012 (4) | 0.006 (3) | 0.009 (3) |
C23 | 0.018 (3) | 0.028 (4) | 0.035 (4) | −0.002 (3) | 0.007 (3) | 0.011 (3) |
C24 | 0.041 (5) | 0.054 (5) | 0.036 (4) | 0.021 (4) | 0.007 (3) | 0.019 (4) |
C25 | 0.072 (6) | 0.087 (7) | 0.041 (5) | 0.051 (6) | 0.015 (4) | 0.032 (5) |
C26 | 0.066 (6) | 0.070 (6) | 0.072 (6) | 0.045 (5) | 0.037 (5) | 0.052 (6) |
C27 | 0.040 (5) | 0.031 (4) | 0.074 (6) | 0.004 (4) | 0.019 (4) | 0.026 (4) |
C28 | 0.025 (4) | 0.037 (4) | 0.052 (5) | 0.004 (3) | 0.003 (3) | 0.017 (4) |
Au—S1 | 2.2883 (19) | C10—H10A | 0.9700 |
Au—P1 | 2.2520 (17) | C10—H10B | 0.9700 |
Fe—C13i | 2.025 (6) | C10—H10C | 0.9700 |
Fe—C13 | 2.025 (6) | C11—H11A | 0.9700 |
Fe—C12 | 2.036 (6) | C11—H11B | 0.9700 |
Fe—C12i | 2.036 (6) | C11—H11C | 0.9700 |
Fe—C16 | 2.039 (7) | C12—C16 | 1.420 (9) |
Fe—C16i | 2.039 (7) | C12—C13 | 1.433 (9) |
Fe—C15 | 2.046 (7) | C13—C14 | 1.403 (10) |
Fe—C15i | 2.046 (7) | C13—H13 | 0.9400 |
Fe—C14i | 2.059 (7) | C14—C15 | 1.416 (11) |
Fe—C14 | 2.059 (7) | C14—H14 | 0.9400 |
S1—C1 | 1.753 (7) | C15—C16 | 1.411 (10) |
P1—C12 | 1.784 (7) | C15—H15 | 0.9400 |
P1—C23 | 1.814 (7) | C16—H16 | 0.9400 |
P1—C17 | 1.818 (6) | C17—C18 | 1.377 (10) |
O1—C1 | 1.370 (9) | C17—C22 | 1.396 (9) |
O1—C9 | 1.479 (8) | C18—C19 | 1.382 (11) |
N1—C1 | 1.253 (9) | C18—H18 | 0.9400 |
N1—C2 | 1.415 (10) | C19—C20 | 1.381 (13) |
C2—C7 | 1.365 (12) | C19—H19 | 0.9400 |
C2—C3 | 1.373 (11) | C20—C21 | 1.358 (12) |
C3—C4 | 1.390 (12) | C20—H20 | 0.9400 |
C3—H3 | 0.9400 | C21—C22 | 1.371 (10) |
C4—C5 | 1.369 (12) | C21—H21 | 0.9400 |
C4—H4 | 0.9400 | C22—H22 | 0.9400 |
C5—C6 | 1.369 (13) | C23—C24 | 1.358 (9) |
C5—C8 | 1.485 (12) | C23—C28 | 1.393 (10) |
C6—C7 | 1.372 (12) | C24—C25 | 1.386 (10) |
C6—H6 | 0.9400 | C24—H24 | 0.9400 |
C7—H7 | 0.9400 | C25—C26 | 1.346 (12) |
C8—H8A | 0.9700 | C25—H25 | 0.9400 |
C8—H8B | 0.9700 | C26—C27 | 1.378 (12) |
C8—H8C | 0.9700 | C26—H26 | 0.9400 |
C9—C11 | 1.488 (11) | C27—C28 | 1.387 (10) |
C9—C10 | 1.519 (10) | C27—H27 | 0.9400 |
C9—H9 | 0.9900 | C28—H28 | 0.9400 |
P1—Au—S1 | 178.17 (8) | O1—C9—C10 | 104.7 (6) |
C13i—Fe—C13 | 180.0 | C11—C9—C10 | 113.9 (7) |
C13i—Fe—C12 | 138.7 (3) | O1—C9—H9 | 109.3 |
C13—Fe—C12 | 41.3 (3) | C11—C9—H9 | 109.3 |
C13i—Fe—C12i | 41.3 (3) | C10—C9—H9 | 109.3 |
C13—Fe—C12i | 138.7 (3) | C9—C10—H10A | 109.5 |
C12—Fe—C12i | 180.0 | C9—C10—H10B | 109.5 |
C13i—Fe—C16 | 111.4 (3) | H10A—C10—H10B | 109.5 |
C13—Fe—C16 | 68.6 (3) | C9—C10—H10C | 109.5 |
C12—Fe—C16 | 40.8 (3) | H10A—C10—H10C | 109.5 |
C12i—Fe—C16 | 139.2 (3) | H10B—C10—H10C | 109.5 |
C13i—Fe—C16i | 68.6 (3) | C9—C11—H11A | 109.5 |
C13—Fe—C16i | 111.4 (3) | C9—C11—H11B | 109.5 |
C12—Fe—C16i | 139.2 (3) | H11A—C11—H11B | 109.5 |
C12i—Fe—C16i | 40.8 (3) | C9—C11—H11C | 109.5 |
C16—Fe—C16i | 180.0 (4) | H11A—C11—H11C | 109.5 |
C13i—Fe—C15 | 112.4 (3) | H11B—C11—H11C | 109.5 |
C13—Fe—C15 | 67.6 (3) | C16—C12—C13 | 106.7 (6) |
C12—Fe—C15 | 68.2 (3) | C16—C12—P1 | 130.5 (5) |
C12i—Fe—C15 | 111.8 (3) | C13—C12—P1 | 122.8 (5) |
C16—Fe—C15 | 40.4 (3) | C16—C12—Fe | 69.7 (4) |
C16i—Fe—C15 | 139.6 (3) | C13—C12—Fe | 68.9 (4) |
C13i—Fe—C15i | 67.6 (3) | P1—C12—Fe | 127.9 (3) |
C13—Fe—C15i | 112.4 (3) | C14—C13—C12 | 109.3 (7) |
C12—Fe—C15i | 111.8 (3) | C14—C13—Fe | 71.2 (4) |
C12i—Fe—C15i | 68.2 (3) | C12—C13—Fe | 69.7 (4) |
C16—Fe—C15i | 139.6 (3) | C14—C13—H13 | 125.4 |
C16i—Fe—C15i | 40.4 (3) | C12—C13—H13 | 125.4 |
C15—Fe—C15i | 180.0 (2) | Fe—C13—H13 | 125.3 |
C13i—Fe—C14i | 40.2 (3) | C13—C14—C15 | 107.0 (7) |
C13—Fe—C14i | 139.8 (3) | C13—C14—Fe | 68.6 (4) |
C12—Fe—C14i | 111.2 (3) | C15—C14—Fe | 69.3 (4) |
C12i—Fe—C14i | 68.8 (3) | C13—C14—H14 | 126.5 |
C16—Fe—C14i | 111.6 (3) | C15—C14—H14 | 126.5 |
C16i—Fe—C14i | 68.4 (3) | Fe—C14—H14 | 127.1 |
C15—Fe—C14i | 139.6 (3) | C16—C15—C14 | 109.2 (7) |
C15i—Fe—C14i | 40.4 (3) | C16—C15—Fe | 69.5 (4) |
C13i—Fe—C14 | 139.8 (3) | C14—C15—Fe | 70.3 (4) |
C13—Fe—C14 | 40.2 (3) | C16—C15—H15 | 125.4 |
C12—Fe—C14 | 68.8 (3) | C14—C15—H15 | 125.4 |
C12i—Fe—C14 | 111.2 (3) | Fe—C15—H15 | 126.3 |
C16—Fe—C14 | 68.4 (3) | C15—C16—C12 | 107.9 (7) |
C16i—Fe—C14 | 111.6 (3) | C15—C16—Fe | 70.1 (4) |
C15—Fe—C14 | 40.4 (3) | C12—C16—Fe | 69.5 (4) |
C15i—Fe—C14 | 139.6 (3) | C15—C16—H16 | 126.0 |
C14i—Fe—C14 | 180.000 (1) | C12—C16—H16 | 126.0 |
C1—S1—Au | 105.7 (3) | Fe—C16—H16 | 126.0 |
C12—P1—C23 | 108.0 (3) | C18—C17—C22 | 119.3 (7) |
C12—P1—C17 | 104.2 (3) | C18—C17—P1 | 118.6 (5) |
C23—P1—C17 | 104.0 (3) | C22—C17—P1 | 122.1 (6) |
C12—P1—Au | 114.8 (2) | C17—C18—C19 | 119.9 (8) |
C23—P1—Au | 110.6 (2) | C17—C18—H18 | 120.0 |
C17—P1—Au | 114.5 (2) | C19—C18—H18 | 120.0 |
C1—O1—C9 | 116.5 (5) | C20—C19—C18 | 120.1 (8) |
C1—N1—C2 | 120.7 (7) | C20—C19—H19 | 120.0 |
N1—C1—O1 | 120.6 (7) | C18—C19—H19 | 120.0 |
N1—C1—S1 | 125.4 (6) | C21—C20—C19 | 120.0 (8) |
O1—C1—S1 | 114.0 (5) | C21—C20—H20 | 120.0 |
C7—C2—C3 | 117.1 (8) | C19—C20—H20 | 120.0 |
C7—C2—N1 | 122.6 (8) | C20—C21—C22 | 120.8 (8) |
C3—C2—N1 | 119.9 (8) | C20—C21—H21 | 119.6 |
C2—C3—C4 | 120.5 (9) | C22—C21—H21 | 119.6 |
C2—C3—H3 | 119.7 | C21—C22—C17 | 119.8 (8) |
C4—C3—H3 | 119.7 | C21—C22—H22 | 120.1 |
C5—C4—C3 | 122.4 (9) | C17—C22—H22 | 120.1 |
C5—C4—H4 | 118.8 | C24—C23—C28 | 119.2 (7) |
C3—C4—H4 | 118.8 | C24—C23—P1 | 119.8 (5) |
C6—C5—C4 | 115.9 (9) | C28—C23—P1 | 121.0 (5) |
C6—C5—C8 | 122.3 (10) | C23—C24—C25 | 120.4 (8) |
C4—C5—C8 | 121.7 (10) | C23—C24—H24 | 119.8 |
C5—C6—C7 | 122.3 (9) | C25—C24—H24 | 119.8 |
C5—C6—H6 | 118.8 | C26—C25—C24 | 120.2 (8) |
C7—C6—H6 | 118.8 | C26—C25—H25 | 119.9 |
C2—C7—C6 | 121.7 (9) | C24—C25—H25 | 119.9 |
C2—C7—H7 | 119.1 | C25—C26—C27 | 121.1 (7) |
C6—C7—H7 | 119.1 | C25—C26—H26 | 119.5 |
C5—C8—H8A | 109.5 | C27—C26—H26 | 119.5 |
C5—C8—H8B | 109.5 | C26—C27—C28 | 118.7 (8) |
H8A—C8—H8B | 109.5 | C26—C27—H27 | 120.6 |
C5—C8—H8C | 109.5 | C28—C27—H27 | 120.6 |
H8A—C8—H8C | 109.5 | C27—C28—C23 | 120.3 (7) |
H8B—C8—H8C | 109.5 | C27—C28—H28 | 119.9 |
O1—C9—C11 | 110.2 (6) | C23—C28—H28 | 119.9 |
C2—N1—C1—O1 | 178.4 (7) | C16—Fe—C14—C13 | 81.9 (5) |
C2—N1—C1—S1 | −3.5 (11) | C16i—Fe—C14—C13 | −98.1 (5) |
C9—O1—C1—N1 | −6.9 (10) | C15—Fe—C14—C13 | 118.9 (6) |
C9—O1—C1—S1 | 174.8 (5) | C15i—Fe—C14—C13 | −61.1 (6) |
Au—S1—C1—N1 | 179.4 (6) | C13i—Fe—C14—C15 | 61.1 (6) |
Au—S1—C1—O1 | −2.4 (6) | C13—Fe—C14—C15 | −118.9 (6) |
C1—N1—C2—C7 | 101.8 (9) | C12—Fe—C14—C15 | −80.9 (5) |
C1—N1—C2—C3 | −85.8 (10) | C12i—Fe—C14—C15 | 99.1 (5) |
C7—C2—C3—C4 | −3.1 (13) | C16—Fe—C14—C15 | −37.0 (4) |
N1—C2—C3—C4 | −175.9 (7) | C16i—Fe—C14—C15 | 143.0 (4) |
C2—C3—C4—C5 | 3.3 (14) | C15i—Fe—C14—C15 | 180.0 |
C3—C4—C5—C6 | −1.7 (13) | C13—C14—C15—C16 | 0.3 (8) |
C3—C4—C5—C8 | −178.0 (9) | Fe—C14—C15—C16 | 58.8 (5) |
C4—C5—C6—C7 | 0.2 (13) | C13—C14—C15—Fe | −58.5 (5) |
C8—C5—C6—C7 | 176.4 (8) | C13i—Fe—C15—C16 | 97.3 (5) |
C3—C2—C7—C6 | 1.7 (12) | C13—Fe—C15—C16 | −82.7 (5) |
N1—C2—C7—C6 | 174.3 (8) | C12—Fe—C15—C16 | −38.0 (4) |
C5—C6—C7—C2 | −0.3 (14) | C12i—Fe—C15—C16 | 142.0 (4) |
C1—O1—C9—C11 | −78.4 (8) | C14i—Fe—C15—C16 | 59.6 (6) |
C1—O1—C9—C10 | 158.6 (6) | C14—Fe—C15—C16 | −120.4 (6) |
C23—P1—C12—C16 | 24.5 (7) | C13i—Fe—C15—C14 | −142.3 (4) |
C17—P1—C12—C16 | −85.7 (6) | C13—Fe—C15—C14 | 37.7 (4) |
Au—P1—C12—C16 | 148.3 (5) | C12—Fe—C15—C14 | 82.4 (5) |
C23—P1—C12—C13 | −158.2 (5) | C12i—Fe—C15—C14 | −97.6 (5) |
C17—P1—C12—C13 | 91.7 (5) | C16—Fe—C15—C14 | 120.4 (6) |
Au—P1—C12—C13 | −34.4 (6) | C16i—Fe—C15—C14 | −59.6 (6) |
C23—P1—C12—Fe | −70.5 (5) | C14—C15—C16—C12 | 0.1 (8) |
C17—P1—C12—Fe | 179.3 (4) | Fe—C15—C16—C12 | 59.4 (5) |
Au—P1—C12—Fe | 53.3 (4) | C14—C15—C16—Fe | −59.3 (5) |
C13i—Fe—C12—C16 | −62.0 (6) | C13—C12—C16—C15 | −0.5 (7) |
C13—Fe—C12—C16 | 118.0 (6) | P1—C12—C16—C15 | 177.2 (5) |
C16i—Fe—C12—C16 | 180.0 | Fe—C12—C16—C15 | −59.8 (5) |
C15—Fe—C12—C16 | 37.6 (4) | C13—C12—C16—Fe | 59.3 (4) |
C15i—Fe—C12—C16 | −142.4 (4) | P1—C12—C16—Fe | −123.0 (6) |
C14i—Fe—C12—C16 | −98.9 (4) | C13i—Fe—C16—C15 | −99.8 (5) |
C14—Fe—C12—C16 | 81.1 (4) | C13—Fe—C16—C15 | 80.2 (5) |
C13i—Fe—C12—C13 | 180.0 | C12—Fe—C16—C15 | 119.0 (6) |
C16—Fe—C12—C13 | −118.0 (6) | C12i—Fe—C16—C15 | −61.0 (6) |
C16i—Fe—C12—C13 | 62.0 (6) | C14i—Fe—C16—C15 | −143.1 (5) |
C15—Fe—C12—C13 | −80.4 (4) | C14—Fe—C16—C15 | 36.9 (5) |
C15i—Fe—C12—C13 | 99.6 (4) | C13i—Fe—C16—C12 | 141.2 (4) |
C14i—Fe—C12—C13 | 143.1 (4) | C13—Fe—C16—C12 | −38.8 (4) |
C14—Fe—C12—C13 | −36.9 (4) | C12i—Fe—C16—C12 | 180.0 |
C13i—Fe—C12—P1 | 64.2 (6) | C15—Fe—C16—C12 | −119.0 (6) |
C13—Fe—C12—P1 | −115.8 (6) | C15i—Fe—C16—C12 | 61.0 (6) |
C16—Fe—C12—P1 | 126.1 (6) | C14i—Fe—C16—C12 | 97.9 (4) |
C16i—Fe—C12—P1 | −53.9 (6) | C14—Fe—C16—C12 | −82.1 (4) |
C15—Fe—C12—P1 | 163.8 (5) | C12—P1—C17—C18 | −177.4 (5) |
C15i—Fe—C12—P1 | −16.2 (5) | C23—P1—C17—C18 | 69.6 (6) |
C14i—Fe—C12—P1 | 27.3 (5) | Au—P1—C17—C18 | −51.2 (6) |
C14—Fe—C12—P1 | −152.7 (5) | C12—P1—C17—C22 | 0.7 (6) |
C16—C12—C13—C14 | 0.7 (7) | C23—P1—C17—C22 | −112.3 (6) |
P1—C12—C13—C14 | −177.2 (5) | Au—P1—C17—C22 | 126.9 (5) |
Fe—C12—C13—C14 | 60.5 (5) | C22—C17—C18—C19 | 2.1 (10) |
C16—C12—C13—Fe | −59.8 (4) | P1—C17—C18—C19 | −179.7 (6) |
P1—C12—C13—Fe | 122.3 (5) | C17—C18—C19—C20 | −1.8 (12) |
C12—Fe—C13—C14 | −119.8 (6) | C18—C19—C20—C21 | 0.2 (13) |
C12i—Fe—C13—C14 | 60.2 (6) | C19—C20—C21—C22 | 1.1 (12) |
C16—Fe—C13—C14 | −81.5 (5) | C20—C21—C22—C17 | −0.8 (12) |
C16i—Fe—C13—C14 | 98.5 (5) | C18—C17—C22—C21 | −0.8 (10) |
C15—Fe—C13—C14 | −37.8 (5) | P1—C17—C22—C21 | −178.9 (6) |
C15i—Fe—C13—C14 | 142.2 (5) | C12—P1—C23—C24 | 106.1 (6) |
C14i—Fe—C13—C14 | 180.0 | C17—P1—C23—C24 | −143.6 (6) |
C12i—Fe—C13—C12 | 180.0 | Au—P1—C23—C24 | −20.2 (6) |
C16—Fe—C13—C12 | 38.3 (4) | C12—P1—C23—C28 | −76.4 (6) |
C16i—Fe—C13—C12 | −141.7 (4) | C17—P1—C23—C28 | 33.9 (7) |
C15—Fe—C13—C12 | 82.0 (4) | Au—P1—C23—C28 | 157.3 (5) |
C15i—Fe—C13—C12 | −98.0 (4) | C28—C23—C24—C25 | −0.3 (12) |
C14i—Fe—C13—C12 | −60.2 (6) | P1—C23—C24—C25 | 177.2 (6) |
C14—Fe—C13—C12 | 119.8 (6) | C23—C24—C25—C26 | 1.0 (13) |
C12—C13—C14—C15 | −0.6 (7) | C24—C25—C26—C27 | −1.8 (14) |
Fe—C13—C14—C15 | 59.0 (5) | C25—C26—C27—C28 | 1.9 (13) |
C12—C13—C14—Fe | −59.6 (4) | C26—C27—C28—C23 | −1.2 (12) |
C13i—Fe—C14—C13 | 180.0 | C24—C23—C28—C27 | 0.4 (11) |
C12—Fe—C14—C13 | 37.9 (4) | P1—C23—C28—C27 | −177.0 (6) |
C12i—Fe—C14—C13 | −142.1 (4) |
Symmetry code: (i) −x+1, −y+1, −z. |
D—H···A | D—H | H···A | D···A | D—H···A |
C25—H25···N1ii | 0.94 | 2.45 | 3.370 (11) | 167 |
Symmetry code: (ii) −x+1, −y+1, −z+1. |
Experimental details
Crystal data | |
Chemical formula | [Au2Fe(C11H14NOS)2(C17H14P)2] |
Mr | 1364.87 |
Crystal system, space group | Triclinic, P1 |
Temperature (K) | 223 |
a, b, c (Å) | 8.1631 (9), 13.4959 (14), 13.5154 (14) |
α, β, γ (°) | 107.440 (2), 97.401 (2), 106.366 (2) |
V (Å3) | 1325.5 (2) |
Z | 1 |
Radiation type | Mo Kα |
µ (mm−1) | 5.97 |
Crystal size (mm) | 0.21 × 0.07 × 0.04 |
Data collection | |
Diffractometer | Bruker SMART CCD diffractometer |
Absorption correction | Multi-scan (SADABS; Bruker, 2000) |
Tmin, Tmax | 0.629, 1 |
No. of measured, independent and observed [I > 2σ(I)] reflections | 7710, 4651, 3790 |
Rint | 0.036 |
(sin θ/λ)max (Å−1) | 0.595 |
Refinement | |
R[F2 > 2σ(F2)], wR(F2), S | 0.040, 0.088, 0.98 |
No. of reflections | 4651 |
No. of parameters | 305 |
H-atom treatment | H-atom parameters constrained |
Δρmax, Δρmin (e Å−3) | 1.74, −0.93 |
Computer programs: SMART (Bruker, 2000), SAINT (Bruker, 2000), PATTY in DIRDIF92 (Beurskens et al., 1992), SHELXL97 (Sheldrick, 2008), DIAMOND (Brandenburg, 2006), publCIF (Westrip, 2009).
D—H···A | D—H | H···A | D···A | D—H···A |
C25—H25···N1i | 0.94 | 2.45 | 3.370 (11) | 167 |
Symmetry code: (i) −x+1, −y+1, −z+1. |
Acknowledgements
The National University of Singapore (grant No. R-143–000–213–112) is thanked for support.
References
Beurskens, P. T., Admiraal, G., Beurskens, G., Bosman, W. P., Garcia-Granda, S., Gould, R. O., Smits, J. M. M. & Smykalla, C. (1992). The DIRDIF Program System. Technical Report. Crystallography Laboratory, University of Nijmegen, The Netherlands. Google Scholar
Brandenburg, K. (2006). DIAMOND. Crystal Impact GbR, Bonn, Germany. Google Scholar
Bruker (2000). SMART, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
Hall, V. J., Siasios, G. & Tiekink, E. R. T. (1993). Aust. J. Chem. 46, 561–570. CSD CrossRef CAS Google Scholar
Ho, S. Y., Cheng, E. C.-C., Tiekink, E. R. T. & Yam, V. W.-W. (2006). Inorg. Chem. 45, 8165–8174. Web of Science CSD CrossRef PubMed CAS Google Scholar
Ho, S. Y. & Tiekink, E. R. T. (2007). CrystEngComm, 9, 368–378. Web of Science CSD CrossRef CAS Google Scholar
Ho, S. Y. & Tiekink, E. R. T. (2009). Acta Cryst. E65, m1466–m1467. Web of Science CSD CrossRef CAS IUCr Journals Google Scholar
Kuan, F. S., Ho, S. Y., Tadbuppa, P. P. & Tiekink, E. R. T. (2008). CrystEngComm, 10, 548–564. Web of Science CSD CrossRef CAS Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar
Westrip, S. P. (2009). publCIF. In preparation. Google Scholar
This is an open-access article distributed under the terms of the Creative Commons Attribution (CC-BY) Licence, which permits unrestricted use, distribution, and reproduction in any medium, provided the original authors and source are cited.
As a part of systematic studies of phosphinegold(I) thiocarbamides (Ho et al. 2006; Ho & Tiekink, 2007; Kuan et al., 2008), the title compound, dppf{Au[SC(O-iPr)NC6H4Me-p]}2, was synthesized, (I); dppf is (Ph2PC5H4)2Fe. The dinuclear molecule has crystallographic symmetry with the Fe atom lying on an inversion centre, Fig. 1.
The gold atom exists in the expected linear geometry defined by a SP donor set, Table 1, and the deviation from linearity [S1–Au–P1 is 178.17 (8) Å] is ascribed to the close approach of the O1 atom, Au···O = 3.079 (4) Å. The anion, with a Z configuration about the C1═N1 bond, shows the expected characteristics. The magnitudes of C1—S1 and C1═N1 of 1.753 (7) and 1.253 (9) Å, respectively, confirm that the anion is coordinating as a thiolate. The overall conformation of the molecule is "open" in that the thiocarbamate ligands are lying on either side of the molecule. This contrasts the situation in each of dppf{Au[SC(OR)NC6H4NO2-p]}2, for R = Me (Ho et al., 2006) and iPr (Ho & Tiekink, 2009), whereby the molecule has a U-shaped conformation allowing for the formation of intramolecular Au···Au interactions.
In the crystal structure of (I), supramolecular chains are formed down the c axis owing to the presence of C–H···N interactions, Table 2 and Fig. 2.