metal-organic compounds
[(Z)-O-Ethyl-N-(p-tolyl)thiocarbamato-κS](triphenylphosphine)-κP]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
The title compound, [Au(C10H12NOS)(C18H15P)], features a linear S,P-donor set about the central Au atom. The thiocarbamate ligand is orientated to place the aryl ring in close proximity to Au [the closest Au⋯C distance is 3.238 (4) Å], which results in a small deviation from the ideal linear P—Au—S geometry.
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 gold⋯π interactions, see: Tiekink & Zukerman-Schpector (2009).
Experimental
Crystal data
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Refinement
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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/S1600536809047618/lh2951sup1.cif
contains datablocks global, I. DOI:Structure factors: contains datablock I. DOI: 10.1107/S1600536809047618/lh2951Isup2.hkl
Compound (I) was prepared following the standard literature procedure from the reaction of Ph3AuCl and EtOC(S)N(H)(p-tolyl) in the presence of base (Hall et al., 1993).
The H atoms were geometrically placed (C—H = 0.94–0.98 Å) and refined as riding with Uiso(H) = 1.2–1.5Ueq(C). The maximum and minimum residual electron density peaks of 1.41 and 0.98 e Å-3, respectively, were located 0.83 Å and 0.81 Å, respectively, 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).Fig. 1. Molecular structure of (I) showing atom-labelling scheme and displacement ellipsoids at the 50% probability level. |
[Au(C10H12NOS)(C18H15P)] | Z = 2 |
Mr = 653.50 | F(000) = 640 |
Triclinic, P1 | Dx = 1.740 Mg m−3 |
Hall symbol: -P 1 | Mo Kα radiation, λ = 0.71069 Å |
a = 8.6676 (5) Å | Cell parameters from 6912 reflections |
b = 12.1397 (6) Å | θ = 2.4–29.9° |
c = 13.2378 (7) Å | µ = 6.07 mm−1 |
α = 65.482 (1)° | T = 223 K |
β = 89.765 (1)° | Block, colourless |
γ = 80.635 (1)° | 0.31 × 0.16 × 0.16 mm |
V = 1247.30 (12) Å3 |
Bruker SMART CCD diffractometer | 5702 independent reflections |
Radiation source: fine-focus sealed tube | 5380 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.019 |
ω scans | θmax = 27.5°, θmin = 1.9° |
Absorption correction: multi-scan (SADABS; Bruker, 2000) | h = −11→11 |
Tmin = 0.311, Tmax = 1 | k = −14→15 |
8852 measured reflections | l = −11→17 |
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)] = 0.025 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.074 | H-atom parameters constrained |
S = 1.04 | w = 1/[σ2(Fo2) + (0.0515P)2 + 0.0366P] where P = (Fo2 + 2Fc2)/3 |
5702 reflections | (Δ/σ)max = 0.001 |
299 parameters | Δρmax = 1.41 e Å−3 |
0 restraints | Δρmin = −0.98 e Å−3 |
[Au(C10H12NOS)(C18H15P)] | γ = 80.635 (1)° |
Mr = 653.50 | V = 1247.30 (12) Å3 |
Triclinic, P1 | Z = 2 |
a = 8.6676 (5) Å | Mo Kα radiation |
b = 12.1397 (6) Å | µ = 6.07 mm−1 |
c = 13.2378 (7) Å | T = 223 K |
α = 65.482 (1)° | 0.31 × 0.16 × 0.16 mm |
β = 89.765 (1)° |
Bruker SMART CCD diffractometer | 5702 independent reflections |
Absorption correction: multi-scan (SADABS; Bruker, 2000) | 5380 reflections with I > 2σ(I) |
Tmin = 0.311, Tmax = 1 | Rint = 0.019 |
8852 measured reflections |
R[F2 > 2σ(F2)] = 0.025 | 0 restraints |
wR(F2) = 0.074 | H-atom parameters constrained |
S = 1.04 | Δρmax = 1.41 e Å−3 |
5702 reflections | Δρmin = −0.98 e Å−3 |
299 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 | 0.133778 (13) | 0.439781 (10) | 0.172306 (9) | 0.03279 (6) | |
S1 | −0.03428 (11) | 0.61652 (8) | 0.06097 (8) | 0.03801 (18) | |
P1 | 0.28847 (10) | 0.26188 (8) | 0.28627 (7) | 0.03056 (17) | |
O1 | −0.1531 (3) | 0.8119 (2) | 0.0773 (2) | 0.0404 (5) | |
N1 | 0.0908 (4) | 0.7459 (3) | 0.1633 (3) | 0.0434 (7) | |
C1 | −0.0164 (4) | 0.7286 (3) | 0.1099 (3) | 0.0341 (6) | |
C2 | 0.2387 (4) | 0.6696 (3) | 0.2015 (3) | 0.0368 (7) | |
C3 | 0.3647 (5) | 0.6845 (4) | 0.1339 (4) | 0.0471 (8) | |
H3 | 0.3482 | 0.7387 | 0.0581 | 0.056* | |
C4 | 0.5130 (5) | 0.6205 (4) | 0.1775 (4) | 0.0473 (9) | |
H4 | 0.5966 | 0.6326 | 0.1308 | 0.057* | |
C5 | 0.5420 (4) | 0.5380 (3) | 0.2896 (3) | 0.0405 (8) | |
C6 | 0.4168 (5) | 0.5244 (3) | 0.3562 (3) | 0.0408 (8) | |
H6 | 0.4331 | 0.4705 | 0.4322 | 0.049* | |
C7 | 0.2677 (4) | 0.5889 (3) | 0.3127 (3) | 0.0400 (8) | |
H7 | 0.1844 | 0.5777 | 0.3596 | 0.048* | |
C8 | 0.7037 (5) | 0.4652 (4) | 0.3367 (4) | 0.0589 (11) | |
H8A | 0.7252 | 0.4645 | 0.4089 | 0.088* | |
H8B | 0.7810 | 0.5029 | 0.2867 | 0.088* | |
H8C | 0.7089 | 0.3815 | 0.3449 | 0.088* | |
C9 | −0.1632 (4) | 0.9157 (3) | 0.1064 (3) | 0.0400 (7) | |
H9A | −0.0921 | 0.9706 | 0.0639 | 0.048* | |
H9B | −0.1352 | 0.8872 | 0.1859 | 0.048* | |
C10 | −0.3300 (5) | 0.9812 (4) | 0.0780 (4) | 0.0523 (10) | |
H10A | −0.3432 | 1.0516 | 0.0964 | 0.078* | |
H10B | −0.3988 | 0.9256 | 0.1203 | 0.078* | |
H10C | −0.3558 | 1.0090 | −0.0009 | 0.078* | |
C11 | 0.4880 (4) | 0.2449 (3) | 0.2467 (3) | 0.0338 (6) | |
C12 | 0.5368 (4) | 0.3463 (3) | 0.1625 (3) | 0.0399 (7) | |
H12 | 0.4657 | 0.4204 | 0.1259 | 0.048* | |
C13 | 0.6905 (5) | 0.3367 (4) | 0.1334 (4) | 0.0540 (10) | |
H13 | 0.7241 | 0.4050 | 0.0778 | 0.065* | |
C14 | 0.7948 (5) | 0.2275 (5) | 0.1856 (4) | 0.0569 (11) | |
H14 | 0.8991 | 0.2221 | 0.1658 | 0.068* | |
C15 | 0.7465 (5) | 0.1256 (4) | 0.2670 (4) | 0.0559 (11) | |
H15 | 0.8175 | 0.0512 | 0.3019 | 0.067* | |
C16 | 0.5923 (5) | 0.1342 (4) | 0.2969 (3) | 0.0439 (8) | |
H16 | 0.5587 | 0.0651 | 0.3512 | 0.053* | |
C17 | 0.2276 (4) | 0.1190 (3) | 0.3033 (3) | 0.0321 (6) | |
C18 | 0.1892 (4) | 0.0357 (3) | 0.4049 (3) | 0.0383 (7) | |
H18 | 0.1924 | 0.0535 | 0.4675 | 0.046* | |
C19 | 0.1460 (5) | −0.0739 (3) | 0.4155 (4) | 0.0444 (8) | |
H19 | 0.1196 | −0.1299 | 0.4846 | 0.053* | |
C20 | 0.1424 (4) | −0.0992 (3) | 0.3228 (4) | 0.0456 (8) | |
H20 | 0.1145 | −0.1733 | 0.3291 | 0.055* | |
C21 | 0.1794 (5) | −0.0163 (4) | 0.2211 (4) | 0.0453 (8) | |
H21 | 0.1759 | −0.0344 | 0.1587 | 0.054* | |
C22 | 0.2216 (4) | 0.0927 (3) | 0.2101 (3) | 0.0400 (8) | |
H22 | 0.2461 | 0.1490 | 0.1404 | 0.048* | |
C23 | 0.2960 (4) | 0.2546 (3) | 0.4263 (3) | 0.0329 (6) | |
C24 | 0.1596 (4) | 0.3020 (3) | 0.4609 (3) | 0.0400 (7) | |
H24 | 0.0671 | 0.3331 | 0.4138 | 0.048* | |
C25 | 0.1605 (5) | 0.3033 (4) | 0.5653 (3) | 0.0483 (9) | |
H25 | 0.0678 | 0.3341 | 0.5892 | 0.058* | |
C26 | 0.2956 (5) | 0.2601 (4) | 0.6341 (3) | 0.0496 (9) | |
H26 | 0.2960 | 0.2643 | 0.7034 | 0.059* | |
C27 | 0.4302 (6) | 0.2107 (4) | 0.6016 (3) | 0.0505 (9) | |
H27 | 0.5214 | 0.1779 | 0.6500 | 0.061* | |
C28 | 0.4315 (4) | 0.2093 (3) | 0.4973 (3) | 0.0421 (8) | |
H28 | 0.5245 | 0.1774 | 0.4745 | 0.051* |
U11 | U22 | U33 | U12 | U13 | U23 | |
Au | 0.03425 (8) | 0.02878 (8) | 0.03499 (9) | −0.00471 (5) | 0.00208 (5) | −0.01337 (6) |
S1 | 0.0414 (4) | 0.0333 (4) | 0.0401 (4) | −0.0021 (3) | −0.0074 (3) | −0.0178 (4) |
P1 | 0.0324 (4) | 0.0270 (4) | 0.0332 (4) | −0.0056 (3) | 0.0028 (3) | −0.0134 (3) |
O1 | 0.0382 (12) | 0.0349 (12) | 0.0474 (14) | 0.0010 (10) | −0.0073 (10) | −0.0193 (11) |
N1 | 0.0396 (16) | 0.0362 (15) | 0.0541 (19) | 0.0010 (13) | −0.0107 (14) | −0.0214 (14) |
C1 | 0.0376 (16) | 0.0299 (15) | 0.0355 (16) | −0.0050 (13) | 0.0019 (13) | −0.0147 (13) |
C2 | 0.0347 (16) | 0.0320 (16) | 0.0493 (19) | −0.0045 (13) | −0.0058 (14) | −0.0229 (15) |
C3 | 0.048 (2) | 0.0419 (19) | 0.048 (2) | −0.0037 (16) | −0.0011 (17) | −0.0176 (17) |
C4 | 0.042 (2) | 0.048 (2) | 0.053 (2) | −0.0086 (17) | 0.0077 (17) | −0.0216 (18) |
C5 | 0.0341 (16) | 0.0389 (18) | 0.056 (2) | −0.0046 (14) | −0.0038 (15) | −0.0279 (17) |
C6 | 0.0454 (19) | 0.0317 (16) | 0.0439 (19) | −0.0042 (15) | −0.0082 (15) | −0.0153 (15) |
C7 | 0.0358 (17) | 0.0353 (17) | 0.051 (2) | −0.0082 (14) | 0.0031 (15) | −0.0194 (16) |
C8 | 0.041 (2) | 0.058 (3) | 0.080 (3) | 0.0024 (19) | −0.013 (2) | −0.034 (2) |
C9 | 0.0420 (18) | 0.0328 (16) | 0.0432 (19) | 0.0000 (14) | 0.0002 (14) | −0.0162 (15) |
C10 | 0.047 (2) | 0.046 (2) | 0.056 (2) | 0.0086 (17) | −0.0033 (18) | −0.0202 (19) |
C11 | 0.0319 (15) | 0.0360 (16) | 0.0370 (16) | −0.0052 (13) | 0.0041 (12) | −0.0190 (14) |
C12 | 0.0380 (17) | 0.0413 (18) | 0.0412 (18) | −0.0096 (14) | 0.0066 (14) | −0.0173 (15) |
C13 | 0.046 (2) | 0.065 (3) | 0.059 (3) | −0.0207 (19) | 0.0164 (19) | −0.029 (2) |
C14 | 0.039 (2) | 0.082 (3) | 0.059 (3) | −0.010 (2) | 0.0087 (19) | −0.039 (3) |
C15 | 0.046 (2) | 0.066 (3) | 0.053 (2) | 0.009 (2) | 0.0006 (18) | −0.028 (2) |
C16 | 0.045 (2) | 0.0393 (19) | 0.045 (2) | −0.0010 (15) | 0.0049 (16) | −0.0185 (16) |
C17 | 0.0294 (14) | 0.0291 (15) | 0.0396 (17) | −0.0053 (12) | −0.0002 (12) | −0.0161 (13) |
C18 | 0.0412 (17) | 0.0340 (17) | 0.0427 (18) | −0.0081 (14) | 0.0037 (14) | −0.0186 (15) |
C19 | 0.045 (2) | 0.0335 (17) | 0.051 (2) | −0.0118 (15) | 0.0093 (16) | −0.0134 (16) |
C20 | 0.0419 (19) | 0.0358 (18) | 0.067 (2) | −0.0097 (15) | 0.0022 (17) | −0.0280 (18) |
C21 | 0.047 (2) | 0.047 (2) | 0.053 (2) | −0.0094 (16) | −0.0005 (16) | −0.0313 (18) |
C22 | 0.0443 (19) | 0.0389 (18) | 0.0398 (18) | −0.0078 (15) | −0.0010 (15) | −0.0191 (15) |
C23 | 0.0380 (16) | 0.0286 (15) | 0.0352 (16) | −0.0098 (12) | 0.0043 (13) | −0.0149 (13) |
C24 | 0.0390 (17) | 0.0413 (18) | 0.0453 (19) | −0.0116 (14) | 0.0076 (14) | −0.0222 (16) |
C25 | 0.054 (2) | 0.052 (2) | 0.049 (2) | −0.0184 (18) | 0.0194 (18) | −0.0282 (19) |
C26 | 0.071 (3) | 0.050 (2) | 0.0357 (18) | −0.026 (2) | 0.0125 (18) | −0.0202 (17) |
C27 | 0.065 (3) | 0.041 (2) | 0.0396 (19) | −0.0112 (18) | −0.0068 (17) | −0.0106 (16) |
C28 | 0.0433 (19) | 0.0403 (18) | 0.0423 (19) | −0.0064 (15) | 0.0006 (15) | −0.0171 (15) |
Au—S1 | 2.2964 (9) | C12—C13 | 1.385 (5) |
Au—P1 | 2.2601 (9) | C12—H12 | 0.9400 |
S1—C1 | 1.759 (3) | C13—C14 | 1.381 (7) |
P1—C11 | 1.810 (3) | C13—H13 | 0.9400 |
P1—C17 | 1.819 (3) | C14—C15 | 1.387 (7) |
P1—C23 | 1.820 (3) | C14—H14 | 0.9400 |
O1—C1 | 1.365 (4) | C15—C16 | 1.392 (6) |
O1—C9 | 1.453 (4) | C15—H15 | 0.9400 |
N1—C1 | 1.265 (5) | C16—H16 | 0.9400 |
N1—C2 | 1.409 (4) | C17—C18 | 1.386 (5) |
C2—C7 | 1.385 (5) | C17—C22 | 1.400 (5) |
C2—C3 | 1.395 (5) | C18—C19 | 1.392 (5) |
C3—C4 | 1.378 (6) | C18—H18 | 0.9400 |
C3—H3 | 0.9400 | C19—C20 | 1.386 (6) |
C4—C5 | 1.400 (6) | C19—H19 | 0.9400 |
C4—H4 | 0.9400 | C20—C21 | 1.380 (6) |
C5—C6 | 1.383 (6) | C20—H20 | 0.9400 |
C5—C8 | 1.510 (5) | C21—C22 | 1.380 (5) |
C6—C7 | 1.385 (5) | C21—H21 | 0.9400 |
C6—H6 | 0.9400 | C22—H22 | 0.9400 |
C7—H7 | 0.9400 | C23—C24 | 1.390 (5) |
C8—H8A | 0.9700 | C23—C28 | 1.391 (5) |
C8—H8B | 0.9700 | C24—C25 | 1.389 (5) |
C8—H8C | 0.9700 | C24—H24 | 0.9400 |
C9—C10 | 1.498 (5) | C25—C26 | 1.374 (6) |
C9—H9A | 0.9800 | C25—H25 | 0.9400 |
C9—H9B | 0.9800 | C26—C27 | 1.374 (6) |
C10—H10A | 0.9700 | C26—H26 | 0.9400 |
C10—H10B | 0.9700 | C27—C28 | 1.388 (6) |
C10—H10C | 0.9700 | C27—H27 | 0.9400 |
C11—C16 | 1.390 (5) | C28—H28 | 0.9400 |
C11—C12 | 1.401 (5) | ||
P1—Au—S1 | 177.07 (3) | C13—C12—C11 | 119.6 (4) |
C1—S1—Au | 107.44 (12) | C13—C12—H12 | 120.2 |
C11—P1—C17 | 103.77 (15) | C11—C12—H12 | 120.2 |
C11—P1—C23 | 107.57 (15) | C14—C13—C12 | 120.4 (4) |
C17—P1—C23 | 104.35 (15) | C14—C13—H13 | 119.8 |
C11—P1—Au | 114.08 (12) | C12—C13—H13 | 119.8 |
C17—P1—Au | 117.45 (11) | C13—C14—C15 | 120.4 (4) |
C23—P1—Au | 108.81 (11) | C13—C14—H14 | 119.8 |
C1—O1—C9 | 116.6 (3) | C15—C14—H14 | 119.8 |
C1—N1—C2 | 125.5 (3) | C14—C15—C16 | 119.7 (4) |
N1—C1—O1 | 118.6 (3) | C14—C15—H15 | 120.2 |
N1—C1—S1 | 134.4 (3) | C16—C15—H15 | 120.2 |
O1—C1—S1 | 107.0 (2) | C11—C16—C15 | 120.1 (4) |
C7—C2—C3 | 118.0 (3) | C11—C16—H16 | 119.9 |
C7—C2—N1 | 119.7 (3) | C15—C16—H16 | 119.9 |
C3—C2—N1 | 121.7 (3) | C18—C17—C22 | 119.4 (3) |
C4—C3—C2 | 120.6 (4) | C18—C17—P1 | 122.3 (3) |
C4—C3—H3 | 119.7 | C22—C17—P1 | 118.3 (3) |
C2—C3—H3 | 119.7 | C17—C18—C19 | 120.9 (3) |
C3—C4—C5 | 121.4 (4) | C17—C18—H18 | 119.6 |
C3—C4—H4 | 119.3 | C19—C18—H18 | 119.6 |
C5—C4—H4 | 119.3 | C20—C19—C18 | 119.0 (4) |
C6—C5—C4 | 117.6 (3) | C20—C19—H19 | 120.5 |
C6—C5—C8 | 120.9 (4) | C18—C19—H19 | 120.5 |
C4—C5—C8 | 121.5 (4) | C21—C20—C19 | 120.5 (3) |
C5—C6—C7 | 121.0 (4) | C21—C20—H20 | 119.8 |
C5—C6—H6 | 119.5 | C19—C20—H20 | 119.8 |
C7—C6—H6 | 119.5 | C20—C21—C22 | 120.7 (4) |
C2—C7—C6 | 121.4 (4) | C20—C21—H21 | 119.6 |
C2—C7—H7 | 119.3 | C22—C21—H21 | 119.6 |
C6—C7—H7 | 119.3 | C21—C22—C17 | 119.5 (4) |
C5—C8—H8A | 109.5 | C21—C22—H22 | 120.2 |
C5—C8—H8B | 109.5 | C17—C22—H22 | 120.2 |
H8A—C8—H8B | 109.5 | C24—C23—C28 | 119.1 (3) |
C5—C8—H8C | 109.5 | C24—C23—P1 | 117.3 (3) |
H8A—C8—H8C | 109.5 | C28—C23—P1 | 123.5 (3) |
H8B—C8—H8C | 109.5 | C25—C24—C23 | 119.7 (4) |
O1—C9—C10 | 106.2 (3) | C25—C24—H24 | 120.2 |
O1—C9—H9A | 110.5 | C23—C24—H24 | 120.2 |
C10—C9—H9A | 110.5 | C26—C25—C24 | 120.7 (4) |
O1—C9—H9B | 110.5 | C26—C25—H25 | 119.7 |
C10—C9—H9B | 110.5 | C24—C25—H25 | 119.7 |
H9A—C9—H9B | 108.7 | C27—C26—C25 | 120.0 (4) |
C9—C10—H10A | 109.5 | C27—C26—H26 | 120.0 |
C9—C10—H10B | 109.5 | C25—C26—H26 | 120.0 |
H10A—C10—H10B | 109.5 | C26—C27—C28 | 120.0 (4) |
C9—C10—H10C | 109.5 | C26—C27—H27 | 120.0 |
H10A—C10—H10C | 109.5 | C28—C27—H27 | 120.0 |
H10B—C10—H10C | 109.5 | C27—C28—C23 | 120.4 (4) |
C16—C11—C12 | 119.7 (3) | C27—C28—H28 | 119.8 |
C16—C11—P1 | 121.7 (3) | C23—C28—H28 | 119.8 |
C12—C11—P1 | 118.6 (3) | ||
C2—N1—C1—O1 | −179.2 (3) | P1—C11—C16—C15 | −177.8 (3) |
C2—N1—C1—S1 | −0.6 (7) | C14—C15—C16—C11 | −1.1 (6) |
C9—O1—C1—N1 | 0.6 (5) | C11—P1—C17—C18 | 116.3 (3) |
C9—O1—C1—S1 | −178.4 (2) | C23—P1—C17—C18 | 3.7 (3) |
Au—S1—C1—N1 | 25.4 (4) | Au—P1—C17—C18 | −116.8 (3) |
Au—S1—C1—O1 | −155.85 (19) | C11—P1—C17—C22 | −62.9 (3) |
C1—N1—C2—C7 | −102.7 (5) | C23—P1—C17—C22 | −175.5 (3) |
C1—N1—C2—C3 | 86.4 (5) | Au—P1—C17—C22 | 64.0 (3) |
C7—C2—C3—C4 | −0.1 (6) | C22—C17—C18—C19 | 0.5 (5) |
N1—C2—C3—C4 | 171.0 (4) | P1—C17—C18—C19 | −178.8 (3) |
C2—C3—C4—C5 | 0.8 (6) | C17—C18—C19—C20 | 0.3 (6) |
C3—C4—C5—C6 | −1.2 (6) | C18—C19—C20—C21 | −0.7 (6) |
C3—C4—C5—C8 | 178.3 (4) | C19—C20—C21—C22 | 0.4 (6) |
C4—C5—C6—C7 | 1.0 (6) | C20—C21—C22—C17 | 0.4 (6) |
C8—C5—C6—C7 | −178.5 (4) | C18—C17—C22—C21 | −0.8 (5) |
C3—C2—C7—C6 | −0.1 (5) | P1—C17—C22—C21 | 178.5 (3) |
N1—C2—C7—C6 | −171.4 (4) | C11—P1—C23—C24 | 160.8 (3) |
C5—C6—C7—C2 | −0.4 (6) | C17—P1—C23—C24 | −89.4 (3) |
C1—O1—C9—C10 | −171.3 (3) | Au—P1—C23—C24 | 36.7 (3) |
C17—P1—C11—C16 | −41.1 (3) | C11—P1—C23—C28 | −16.4 (3) |
C23—P1—C11—C16 | 69.1 (3) | C17—P1—C23—C28 | 93.4 (3) |
Au—P1—C11—C16 | −170.1 (3) | Au—P1—C23—C28 | −140.5 (3) |
C17—P1—C11—C12 | 138.3 (3) | C28—C23—C24—C25 | −0.1 (5) |
C23—P1—C11—C12 | −111.5 (3) | P1—C23—C24—C25 | −177.4 (3) |
Au—P1—C11—C12 | 9.3 (3) | C23—C24—C25—C26 | 1.1 (6) |
C16—C11—C12—C13 | −2.7 (5) | C24—C25—C26—C27 | −2.4 (6) |
P1—C11—C12—C13 | 177.8 (3) | C25—C26—C27—C28 | 2.7 (6) |
C11—C12—C13—C14 | 1.0 (6) | C26—C27—C28—C23 | −1.7 (6) |
C12—C13—C14—C15 | 0.6 (7) | C24—C23—C28—C27 | 0.4 (5) |
C13—C14—C15—C16 | −0.6 (7) | P1—C23—C28—C27 | 177.6 (3) |
C12—C11—C16—C15 | 2.7 (6) |
Experimental details
Crystal data | |
Chemical formula | [Au(C10H12NOS)(C18H15P)] |
Mr | 653.50 |
Crystal system, space group | Triclinic, P1 |
Temperature (K) | 223 |
a, b, c (Å) | 8.6676 (5), 12.1397 (6), 13.2378 (7) |
α, β, γ (°) | 65.482 (1), 89.765 (1), 80.635 (1) |
V (Å3) | 1247.30 (12) |
Z | 2 |
Radiation type | Mo Kα |
µ (mm−1) | 6.07 |
Crystal size (mm) | 0.31 × 0.16 × 0.16 |
Data collection | |
Diffractometer | Bruker SMART CCD diffractometer |
Absorption correction | Multi-scan (SADABS; Bruker, 2000) |
Tmin, Tmax | 0.311, 1 |
No. of measured, independent and observed [I > 2σ(I)] reflections | 8852, 5702, 5380 |
Rint | 0.019 |
(sin θ/λ)max (Å−1) | 0.650 |
Refinement | |
R[F2 > 2σ(F2)], wR(F2), S | 0.025, 0.074, 1.04 |
No. of reflections | 5702 |
No. of parameters | 299 |
H-atom treatment | H-atom parameters constrained |
Δρmax, Δρmin (e Å−3) | 1.41, −0.98 |
Computer programs: SMART (Bruker, 2000), SAINT (Bruker, 2000), PATTY in DIRDIF92 (Beurskens et al., 1992), SHELXL97 (Sheldrick, 2008), DIAMOND (Brandenburg, 2006), publCIF (Westrip, 2009).
Acknowledgements
The National University of Singapore (grant No. R-143–000–213–112) is thanked for support.
References
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Phosphinegold(I) thiocarbamides have proved relatively easy to crystallize making systematic structural investigations possible, such as monitoring the influence of phosphine and/or thiocarbamato ligands upon supramolecular aggregation patterns (Ho & Tiekink, 2007; Kuan et al., 2008) and luminescence (Ho et al. 2006). During these studies, the title compound, Ph3Au[SC(OEt)N(p-tolyl)], (I), was synthesized.
The gold atom in (I) exists in the expected linear geometry defined by a S,P donor set, Table 1 and Fig. 1. While the thiocarbamato anion shows the expected features, i.e. a Z-conformation about the C1-N1 bond and thiolate character [C1–S1 is 1.759 (3) Å and C1-N1 is 1.265 (5) Å], its orientation within the molecule is unusual. Normally in these type of phosphinegold(I) compounds, the orientation of the thiocarbamato ligand has the O1 atom in close proximity to the Au atom. However, in (I), the aryl ring is orientated towards Au [closest Au···C2 distance = 3.238 (4) Å, and Au···Cg(C2—C7) = 3.60 Å]. The close approach of the aryl ring is responsible for the small deviation from linearity of the S,P donor set, Table 1.
Electronic and steric effects have been cited as reasons for the variation in the coordination modes of thiocarbamato ligands in their phosphinegold(I) compounds, with N-bound p-tolyl groups known to promote Au···π interactions (Kuan et al., 2008).