metal-organic compounds
[(Z)-O-Ethyl-N-(o-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 geometry for the Au atom defined by the S and P donor atoms. A small deviation from the ideal geometry is noted and is ascribed to an intramolecular Au⋯O contact [2.936 (4) Å]. Inversion dimers are formed in the mediated by C—H⋯π interactions between centrosymmetrically related o-tolyl residues [C⋯Cg = 3.532 (6) Å].
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).
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/S1600536809048466/sj2686sup1.cif
contains datablocks global, I. DOI:Structure factors: contains datablock I. DOI: 10.1107/S1600536809048466/sj2686Isup2.hkl
Compound (I) was prepared following the standard literature procedure from the reaction of Ph3AuCl and EtOC(S)N(H)(o-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 1.62 and 1.26 e Å-3, respectively, were located 0.81 Å and 0.92 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\bbr09).[Au(C10H12NOS)(C18H15P)] | Z = 2 |
Mr = 653.50 | F(000) = 640 |
Triclinic, P1 | Dx = 1.716 Mg m−3 |
Hall symbol: -P 1 | Mo Kα radiation, λ = 0.71069 Å |
a = 9.3378 (6) Å | Cell parameters from 5740 reflections |
b = 10.1665 (6) Å | θ = 2.3–29.9° |
c = 13.9711 (8) Å | µ = 5.98 mm−1 |
α = 95.514 (1)° | T = 223 K |
β = 103.371 (1)° | Block, colourless |
γ = 98.334 (1)° | 0.24 × 0.13 × 0.03 mm |
V = 1265.11 (13) Å3 |
Bruker SMART CCD diffractometer | 5772 independent reflections |
Radiation source: fine-focus sealed tube | 5279 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.023 |
ω scans | θmax = 27.5°, θmin = 1.5° |
Absorption correction: multi-scan (SADABS; Bruker, 2000) | h = −12→11 |
Tmin = 0.311, Tmax = 1 | k = −10→13 |
8823 measured reflections | l = −17→18 |
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)] = 0.031 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.104 | H-atom parameters constrained |
S = 1.07 | w = 1/[σ2(Fo2) + (0.0692P)2] where P = (Fo2 + 2Fc2)/3 |
5772 reflections | (Δ/σ)max = 0.001 |
299 parameters | Δρmax = 1.62 e Å−3 |
0 restraints | Δρmin = −1.26 e Å−3 |
[Au(C10H12NOS)(C18H15P)] | γ = 98.334 (1)° |
Mr = 653.50 | V = 1265.11 (13) Å3 |
Triclinic, P1 | Z = 2 |
a = 9.3378 (6) Å | Mo Kα radiation |
b = 10.1665 (6) Å | µ = 5.98 mm−1 |
c = 13.9711 (8) Å | T = 223 K |
α = 95.514 (1)° | 0.24 × 0.13 × 0.03 mm |
β = 103.371 (1)° |
Bruker SMART CCD diffractometer | 5772 independent reflections |
Absorption correction: multi-scan (SADABS; Bruker, 2000) | 5279 reflections with I > 2σ(I) |
Tmin = 0.311, Tmax = 1 | Rint = 0.023 |
8823 measured reflections |
R[F2 > 2σ(F2)] = 0.031 | 0 restraints |
wR(F2) = 0.104 | H-atom parameters constrained |
S = 1.07 | Δρmax = 1.62 e Å−3 |
5772 reflections | Δρmin = −1.26 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 | 0.147930 (18) | 0.358507 (16) | 0.308910 (12) | 0.03424 (8) | |
S1 | −0.00461 (14) | 0.49405 (12) | 0.22765 (9) | 0.0352 (2) | |
P1 | 0.28887 (13) | 0.21714 (12) | 0.38273 (9) | 0.0305 (2) | |
O1 | −0.1318 (4) | 0.2462 (3) | 0.1600 (3) | 0.0419 (8) | |
N1 | −0.2434 (5) | 0.3967 (4) | 0.0724 (3) | 0.0392 (9) | |
C1 | −0.1424 (5) | 0.3740 (5) | 0.1420 (3) | 0.0340 (9) | |
C2 | −0.2509 (5) | 0.5300 (5) | 0.0506 (4) | 0.0368 (10) | |
C3 | −0.3452 (5) | 0.6059 (5) | 0.0885 (3) | 0.0375 (10) | |
C4 | −0.3575 (6) | 0.7297 (5) | 0.0590 (4) | 0.0435 (11) | |
H4 | −0.4198 | 0.7813 | 0.0840 | 0.052* | |
C5 | −0.2799 (6) | 0.7804 (6) | −0.0070 (4) | 0.0483 (13) | |
H5 | −0.2893 | 0.8658 | −0.0256 | 0.058* | |
C6 | −0.1902 (6) | 0.7060 (6) | −0.0448 (4) | 0.0447 (12) | |
H6 | −0.1390 | 0.7395 | −0.0903 | 0.054* | |
C7 | −0.1747 (5) | 0.5813 (6) | −0.0160 (4) | 0.0412 (11) | |
H7 | −0.1120 | 0.5307 | −0.0417 | 0.049* | |
C8 | −0.4332 (6) | 0.5472 (6) | 0.1575 (4) | 0.0461 (12) | |
H8A | −0.4931 | 0.6107 | 0.1765 | 0.069* | |
H8B | −0.3648 | 0.5289 | 0.2164 | 0.069* | |
H8C | −0.4981 | 0.4645 | 0.1238 | 0.069* | |
C9 | −0.2431 (6) | 0.1389 (5) | 0.0974 (4) | 0.0476 (12) | |
H9A | −0.1996 | 0.0572 | 0.0923 | 0.057* | |
H9B | −0.2735 | 0.1637 | 0.0305 | 0.057* | |
C10 | −0.3760 (7) | 0.1122 (7) | 0.1382 (5) | 0.0568 (15) | |
H10A | −0.4484 | 0.0400 | 0.0952 | 0.085* | |
H10B | −0.4203 | 0.1925 | 0.1420 | 0.085* | |
H10C | −0.3462 | 0.0866 | 0.2040 | 0.085* | |
C11 | 0.4873 (5) | 0.2811 (5) | 0.4272 (4) | 0.0336 (9) | |
C12 | 0.5675 (6) | 0.2763 (5) | 0.5233 (4) | 0.0425 (11) | |
H12 | 0.5166 | 0.2442 | 0.5694 | 0.051* | |
C13 | 0.7199 (6) | 0.3175 (6) | 0.5527 (4) | 0.0490 (13) | |
H13 | 0.7724 | 0.3139 | 0.6182 | 0.059* | |
C14 | 0.7945 (6) | 0.3639 (6) | 0.4854 (5) | 0.0523 (14) | |
H14 | 0.8989 | 0.3902 | 0.5047 | 0.063* | |
C15 | 0.7178 (6) | 0.3723 (6) | 0.3895 (5) | 0.0509 (13) | |
H15 | 0.7697 | 0.4056 | 0.3443 | 0.061* | |
C16 | 0.5622 (6) | 0.3310 (5) | 0.3600 (4) | 0.0449 (11) | |
H16 | 0.5092 | 0.3372 | 0.2951 | 0.054* | |
C17 | 0.2775 (5) | 0.0655 (4) | 0.2989 (3) | 0.0317 (9) | |
C18 | 0.3943 (6) | −0.0073 (5) | 0.3093 (4) | 0.0413 (11) | |
H18 | 0.4832 | 0.0241 | 0.3587 | 0.050* | |
C19 | 0.3800 (7) | −0.1259 (6) | 0.2472 (4) | 0.0479 (13) | |
H19 | 0.4599 | −0.1736 | 0.2534 | 0.058* | |
C20 | 0.2469 (8) | −0.1739 (6) | 0.1757 (5) | 0.0550 (14) | |
H20 | 0.2355 | −0.2559 | 0.1351 | 0.066* | |
C21 | 0.1319 (7) | −0.1011 (7) | 0.1645 (5) | 0.0578 (15) | |
H21 | 0.0427 | −0.1331 | 0.1155 | 0.069* | |
C22 | 0.1467 (6) | 0.0183 (6) | 0.2245 (4) | 0.0436 (11) | |
H22 | 0.0685 | 0.0682 | 0.2153 | 0.052* | |
C23 | 0.2305 (5) | 0.1605 (5) | 0.4895 (3) | 0.0328 (9) | |
C24 | 0.2240 (6) | 0.0302 (5) | 0.5088 (4) | 0.0389 (10) | |
H24 | 0.2465 | −0.0348 | 0.4647 | 0.047* | |
C25 | 0.1840 (6) | −0.0054 (6) | 0.5941 (4) | 0.0478 (12) | |
H25 | 0.1777 | −0.0949 | 0.6068 | 0.057* | |
C26 | 0.1532 (6) | 0.0910 (6) | 0.6604 (4) | 0.0467 (12) | |
H26 | 0.1288 | 0.0670 | 0.7188 | 0.056* | |
C27 | 0.1583 (7) | 0.2195 (6) | 0.6411 (4) | 0.0502 (13) | |
H27 | 0.1370 | 0.2843 | 0.6860 | 0.060* | |
C28 | 0.1950 (6) | 0.2562 (5) | 0.5551 (4) | 0.0425 (11) | |
H28 | 0.1959 | 0.3449 | 0.5412 | 0.051* |
U11 | U22 | U33 | U12 | U13 | U23 | |
Au | 0.03477 (12) | 0.03251 (12) | 0.03386 (12) | 0.01184 (8) | 0.00062 (8) | 0.00697 (7) |
S1 | 0.0354 (6) | 0.0300 (5) | 0.0369 (6) | 0.0114 (4) | −0.0012 (5) | 0.0052 (4) |
P1 | 0.0305 (5) | 0.0294 (6) | 0.0300 (6) | 0.0095 (4) | 0.0012 (4) | 0.0054 (4) |
O1 | 0.0446 (19) | 0.0308 (17) | 0.0437 (19) | 0.0065 (14) | −0.0023 (15) | 0.0060 (14) |
N1 | 0.038 (2) | 0.037 (2) | 0.041 (2) | 0.0108 (17) | 0.0020 (17) | 0.0072 (17) |
C1 | 0.035 (2) | 0.030 (2) | 0.036 (2) | 0.0089 (18) | 0.0053 (19) | 0.0039 (18) |
C2 | 0.028 (2) | 0.040 (3) | 0.036 (2) | 0.0070 (19) | −0.0033 (18) | 0.0013 (19) |
C3 | 0.039 (2) | 0.041 (3) | 0.030 (2) | 0.011 (2) | 0.0010 (19) | 0.0030 (19) |
C4 | 0.044 (3) | 0.044 (3) | 0.040 (3) | 0.012 (2) | 0.005 (2) | −0.001 (2) |
C5 | 0.052 (3) | 0.038 (3) | 0.047 (3) | 0.003 (2) | 0.000 (2) | 0.008 (2) |
C6 | 0.044 (3) | 0.045 (3) | 0.043 (3) | 0.004 (2) | 0.004 (2) | 0.012 (2) |
C7 | 0.034 (2) | 0.047 (3) | 0.043 (3) | 0.016 (2) | 0.004 (2) | 0.007 (2) |
C8 | 0.048 (3) | 0.053 (3) | 0.039 (3) | 0.015 (2) | 0.011 (2) | 0.005 (2) |
C9 | 0.053 (3) | 0.031 (2) | 0.050 (3) | 0.007 (2) | −0.002 (2) | −0.001 (2) |
C10 | 0.047 (3) | 0.053 (3) | 0.065 (4) | 0.005 (3) | 0.002 (3) | 0.013 (3) |
C11 | 0.030 (2) | 0.029 (2) | 0.038 (2) | 0.0040 (17) | 0.0017 (18) | 0.0047 (18) |
C12 | 0.042 (3) | 0.038 (3) | 0.041 (3) | 0.000 (2) | 0.002 (2) | 0.005 (2) |
C13 | 0.039 (3) | 0.042 (3) | 0.052 (3) | 0.005 (2) | −0.013 (2) | 0.001 (2) |
C14 | 0.034 (3) | 0.038 (3) | 0.077 (4) | 0.000 (2) | 0.002 (3) | 0.004 (3) |
C15 | 0.046 (3) | 0.040 (3) | 0.068 (4) | −0.002 (2) | 0.023 (3) | 0.007 (3) |
C16 | 0.047 (3) | 0.041 (3) | 0.047 (3) | 0.010 (2) | 0.010 (2) | 0.010 (2) |
C17 | 0.033 (2) | 0.028 (2) | 0.034 (2) | 0.0051 (17) | 0.0085 (18) | 0.0054 (17) |
C18 | 0.046 (3) | 0.041 (3) | 0.036 (2) | 0.009 (2) | 0.008 (2) | 0.003 (2) |
C19 | 0.063 (4) | 0.039 (3) | 0.049 (3) | 0.016 (3) | 0.023 (3) | 0.007 (2) |
C20 | 0.075 (4) | 0.039 (3) | 0.051 (3) | 0.005 (3) | 0.023 (3) | −0.006 (2) |
C21 | 0.057 (3) | 0.058 (4) | 0.047 (3) | −0.002 (3) | 0.002 (3) | −0.007 (3) |
C22 | 0.036 (2) | 0.049 (3) | 0.037 (3) | 0.001 (2) | 0.000 (2) | −0.001 (2) |
C23 | 0.032 (2) | 0.036 (2) | 0.031 (2) | 0.0124 (18) | 0.0045 (17) | 0.0039 (18) |
C24 | 0.044 (3) | 0.037 (2) | 0.039 (3) | 0.014 (2) | 0.009 (2) | 0.010 (2) |
C25 | 0.056 (3) | 0.045 (3) | 0.046 (3) | 0.010 (2) | 0.015 (2) | 0.013 (2) |
C26 | 0.044 (3) | 0.058 (3) | 0.041 (3) | 0.010 (2) | 0.014 (2) | 0.010 (2) |
C27 | 0.050 (3) | 0.059 (4) | 0.042 (3) | 0.014 (3) | 0.016 (2) | −0.007 (3) |
C28 | 0.047 (3) | 0.037 (3) | 0.045 (3) | 0.015 (2) | 0.011 (2) | −0.001 (2) |
Au—S1 | 2.3105 (11) | C12—C13 | 1.375 (7) |
Au—P1 | 2.2509 (11) | C12—H12 | 0.9400 |
S1—C1 | 1.768 (5) | C13—C14 | 1.373 (9) |
P1—C11 | 1.812 (5) | C13—H13 | 0.9400 |
P1—C23 | 1.817 (5) | C14—C15 | 1.382 (9) |
P1—C17 | 1.819 (5) | C14—H14 | 0.9400 |
O1—C1 | 1.360 (6) | C15—C16 | 1.403 (8) |
O1—C9 | 1.450 (6) | C15—H15 | 0.9400 |
N1—C1 | 1.254 (6) | C16—H16 | 0.9400 |
N1—C2 | 1.425 (6) | C17—C18 | 1.392 (7) |
C2—C7 | 1.391 (7) | C17—C22 | 1.396 (6) |
C2—C3 | 1.410 (7) | C18—C19 | 1.386 (8) |
C3—C4 | 1.374 (7) | C18—H18 | 0.9400 |
C3—C8 | 1.514 (7) | C19—C20 | 1.392 (9) |
C4—C5 | 1.390 (8) | C19—H19 | 0.9400 |
C4—H4 | 0.9400 | C20—C21 | 1.379 (9) |
C5—C6 | 1.366 (8) | C20—H20 | 0.9400 |
C5—H5 | 0.9400 | C21—C22 | 1.377 (8) |
C6—C7 | 1.384 (7) | C21—H21 | 0.9400 |
C6—H6 | 0.9400 | C22—H22 | 0.9400 |
C7—H7 | 0.9400 | C23—C24 | 1.372 (7) |
C8—H8A | 0.9700 | C23—C28 | 1.401 (7) |
C8—H8B | 0.9700 | C24—C25 | 1.393 (7) |
C8—H8C | 0.9700 | C24—H24 | 0.9400 |
C9—C10 | 1.482 (9) | C25—C26 | 1.390 (8) |
C9—H9A | 0.9800 | C25—H25 | 0.9400 |
C9—H9B | 0.9800 | C26—C27 | 1.356 (9) |
C10—H10A | 0.9700 | C26—H26 | 0.9400 |
C10—H10B | 0.9700 | C27—C28 | 1.392 (8) |
C10—H10C | 0.9700 | C27—H27 | 0.9400 |
C11—C16 | 1.387 (7) | C28—H28 | 0.9400 |
C11—C12 | 1.387 (7) | ||
P1—Au—S1 | 177.00 (4) | C13—C12—C11 | 121.4 (5) |
C1—S1—Au | 101.39 (16) | C13—C12—H12 | 119.3 |
C11—P1—C23 | 105.3 (2) | C11—C12—H12 | 119.3 |
C11—P1—C17 | 104.4 (2) | C14—C13—C12 | 119.4 (5) |
C23—P1—C17 | 105.6 (2) | C14—C13—H13 | 120.3 |
C11—P1—Au | 116.15 (15) | C12—C13—H13 | 120.3 |
C23—P1—Au | 112.80 (15) | C13—C14—C15 | 120.7 (5) |
C17—P1—Au | 111.68 (15) | C13—C14—H14 | 119.6 |
C1—O1—C9 | 117.5 (4) | C15—C14—H14 | 119.6 |
C1—N1—C2 | 120.8 (4) | C14—C15—C16 | 119.7 (5) |
N1—C1—O1 | 120.6 (4) | C14—C15—H15 | 120.1 |
N1—C1—S1 | 127.0 (4) | C16—C15—H15 | 120.1 |
O1—C1—S1 | 112.4 (3) | C11—C16—C15 | 119.5 (5) |
C7—C2—C3 | 119.5 (5) | C11—C16—H16 | 120.2 |
C7—C2—N1 | 119.5 (5) | C15—C16—H16 | 120.2 |
C3—C2—N1 | 120.7 (5) | C18—C17—C22 | 119.2 (5) |
C4—C3—C2 | 118.4 (5) | C18—C17—P1 | 121.5 (4) |
C4—C3—C8 | 122.2 (5) | C22—C17—P1 | 119.3 (4) |
C2—C3—C8 | 119.3 (5) | C19—C18—C17 | 120.4 (5) |
C3—C4—C5 | 121.6 (5) | C19—C18—H18 | 119.8 |
C3—C4—H4 | 119.2 | C17—C18—H18 | 119.8 |
C5—C4—H4 | 119.2 | C18—C19—C20 | 119.8 (6) |
C6—C5—C4 | 119.9 (5) | C18—C19—H19 | 120.1 |
C6—C5—H5 | 120.1 | C20—C19—H19 | 120.1 |
C4—C5—H5 | 120.1 | C21—C20—C19 | 119.9 (5) |
C5—C6—C7 | 120.0 (5) | C21—C20—H20 | 120.0 |
C5—C6—H6 | 120.0 | C19—C20—H20 | 120.0 |
C7—C6—H6 | 120.0 | C22—C21—C20 | 120.5 (6) |
C6—C7—C2 | 120.6 (5) | C22—C21—H21 | 119.7 |
C6—C7—H7 | 119.7 | C20—C21—H21 | 119.7 |
C2—C7—H7 | 119.7 | C21—C22—C17 | 120.2 (5) |
C3—C8—H8A | 109.5 | C21—C22—H22 | 119.9 |
C3—C8—H8B | 109.5 | C17—C22—H22 | 119.9 |
H8A—C8—H8B | 109.5 | C24—C23—C28 | 119.6 (5) |
C3—C8—H8C | 109.5 | C24—C23—P1 | 122.8 (4) |
H8A—C8—H8C | 109.5 | C28—C23—P1 | 117.6 (4) |
H8B—C8—H8C | 109.5 | C23—C24—C25 | 119.9 (5) |
O1—C9—C10 | 111.1 (5) | C23—C24—H24 | 120.1 |
O1—C9—H9A | 109.4 | C25—C24—H24 | 120.1 |
C10—C9—H9A | 109.4 | C26—C25—C24 | 120.2 (5) |
O1—C9—H9B | 109.4 | C26—C25—H25 | 119.9 |
C10—C9—H9B | 109.4 | C24—C25—H25 | 119.9 |
H9A—C9—H9B | 108.0 | C27—C26—C25 | 120.1 (5) |
C9—C10—H10A | 109.5 | C27—C26—H26 | 119.9 |
C9—C10—H10B | 109.5 | C25—C26—H26 | 119.9 |
H10A—C10—H10B | 109.5 | C26—C27—C28 | 120.4 (5) |
C9—C10—H10C | 109.5 | C26—C27—H27 | 119.8 |
H10A—C10—H10C | 109.5 | C28—C27—H27 | 119.8 |
H10B—C10—H10C | 109.5 | C27—C28—C23 | 119.8 (5) |
C16—C11—C12 | 119.2 (5) | C27—C28—H28 | 120.1 |
C16—C11—P1 | 117.8 (4) | C23—C28—H28 | 120.1 |
C12—C11—P1 | 123.0 (4) | ||
C2—N1—C1—O1 | −177.2 (4) | C12—C11—C16—C15 | 1.7 (8) |
C2—N1—C1—S1 | 4.3 (7) | P1—C11—C16—C15 | −175.3 (4) |
C9—O1—C1—N1 | −1.4 (7) | C14—C15—C16—C11 | −0.5 (8) |
C9—O1—C1—S1 | 177.3 (4) | C11—P1—C17—C18 | 26.2 (4) |
Au—S1—C1—N1 | −171.6 (4) | C23—P1—C17—C18 | −84.6 (4) |
Au—S1—C1—O1 | 9.8 (4) | Au—P1—C17—C18 | 152.4 (4) |
C1—N1—C2—C7 | 89.5 (6) | C11—P1—C17—C22 | −156.2 (4) |
C1—N1—C2—C3 | −96.3 (6) | C23—P1—C17—C22 | 93.0 (4) |
C7—C2—C3—C4 | −0.7 (7) | Au—P1—C17—C22 | −29.9 (4) |
N1—C2—C3—C4 | −174.9 (4) | C22—C17—C18—C19 | −0.7 (7) |
C7—C2—C3—C8 | 177.4 (5) | P1—C17—C18—C19 | 177.0 (4) |
N1—C2—C3—C8 | 3.1 (7) | C17—C18—C19—C20 | −1.5 (8) |
C2—C3—C4—C5 | 0.2 (8) | C18—C19—C20—C21 | 2.3 (9) |
C8—C3—C4—C5 | −177.8 (5) | C19—C20—C21—C22 | −0.9 (10) |
C3—C4—C5—C6 | 0.7 (8) | C20—C21—C22—C17 | −1.3 (9) |
C4—C5—C6—C7 | −1.1 (8) | C18—C17—C22—C21 | 2.1 (8) |
C5—C6—C7—C2 | 0.6 (8) | P1—C17—C22—C21 | −175.6 (4) |
C3—C2—C7—C6 | 0.3 (7) | C11—P1—C23—C24 | −93.8 (4) |
N1—C2—C7—C6 | 174.6 (5) | C17—P1—C23—C24 | 16.3 (5) |
C1—O1—C9—C10 | −88.1 (6) | Au—P1—C23—C24 | 138.5 (4) |
C23—P1—C11—C16 | 179.7 (4) | C11—P1—C23—C28 | 84.5 (4) |
C17—P1—C11—C16 | 68.7 (4) | C17—P1—C23—C28 | −165.4 (4) |
Au—P1—C11—C16 | −54.7 (4) | Au—P1—C23—C28 | −43.2 (4) |
C23—P1—C11—C12 | 2.8 (5) | C28—C23—C24—C25 | −0.8 (8) |
C17—P1—C11—C12 | −108.2 (4) | P1—C23—C24—C25 | 177.5 (4) |
Au—P1—C11—C12 | 128.4 (4) | C23—C24—C25—C26 | −1.1 (8) |
C16—C11—C12—C13 | −1.3 (8) | C24—C25—C26—C27 | 1.7 (9) |
P1—C11—C12—C13 | 175.5 (4) | C25—C26—C27—C28 | −0.3 (9) |
C11—C12—C13—C14 | −0.3 (9) | C26—C27—C28—C23 | −1.6 (9) |
C12—C13—C14—C15 | 1.4 (9) | C24—C23—C28—C27 | 2.2 (8) |
C13—C14—C15—C16 | −1.0 (9) | P1—C23—C28—C27 | −176.2 (4) |
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) | 9.3378 (6), 10.1665 (6), 13.9711 (8) |
α, β, γ (°) | 95.514 (1), 103.371 (1), 98.334 (1) |
V (Å3) | 1265.11 (13) |
Z | 2 |
Radiation type | Mo Kα |
µ (mm−1) | 5.98 |
Crystal size (mm) | 0.24 × 0.13 × 0.03 |
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 | 8823, 5772, 5279 |
Rint | 0.023 |
(sin θ/λ)max (Å−1) | 0.650 |
Refinement | |
R[F2 > 2σ(F2)], wR(F2), S | 0.031, 0.104, 1.07 |
No. of reflections | 5772 |
No. of parameters | 299 |
H-atom treatment | H-atom parameters constrained |
Δρmax, Δρmin (e Å−3) | 1.62, −1.26 |
Computer programs: SMART (Bruker, 2000), SAINT (Bruker, 2000), PATTY in DIRDIF92 (Beurskens et al., 1992), SHELXL97 (Sheldrick, 2008), DIAMOND (Brandenburg, 2006), publCIF (Westrip, 2009\bbr09).
Acknowledgements
The National University of Singapore (grant No. R-143–000–213–112) is thanked for support.
References
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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.
The title compound, Ph3Au[SC(OEt)N(o-tolyl), (I), was synthesized during the course of systematic studies of phosphinegold(I) thiocarbamides (Ho et al. 2006; Ho & Tiekink, 2007; Kuan et al., 2008)..
The gold atom in (I) exists in a linear geometry defined by an S,P donor set, Table 1 and Fig. 1. The small deviation from linearity is due to the close approach of the O1 atom to Au [Au···O = 2.936 (4) Å]. The anion, having C1—S1 = 1.768 (5) Å and C1N1 = 1.254 (6) Å, coordinates as a thiolate ligand. The configuration about the C1N1 double bond is Z.
In the crystal structure of (I), supramolecular dimers are formed between centrosymmetric pairs of o-tolyl residues owing to the presence of C—H···π interactions whereby the π system is defined by the (C2–C7) ring; C8–H8c···Cgi = 2.67 Å, C8···Cgi = 3.532 (6) Å with an angle at H8c = 148 ° for i: -1 - x, 1 - y, -z.