Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S0108270100007319/sk1392sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S0108270100007319/sk1392Isup2.hkl |
CCDC reference: 150314
Sodium N,N'-diisopropyldithiocarbamate, Na(S2CNiPr2), dissolved in H2O was added to gold trichloride at room temperature with stirring. The brown reaction mixture was filtered and the filtrate was washed with water and dried overnight in a vacuum. The brown solid obtained was dissolved in butane. Triphenylphosphine was added at 353–363 K with stirring and the solution was refluxed for 4–5 h before cooling. Single crystals of (I) suitable for X-ray analysis were grown by slow evaporation at room temperature for a period of two weeks.
The butane solvent is disordered and so has a higher atomic displacement parameter ratio for a few atoms. All H atoms were fixed geometrically at calculated distances and allowed to ride on their parent atoms. The maximum and minimum electron densities (1.31 and −1.46 e Å−3) were observed at distances of 1.05 and 0.89 Å, respectively, from the Au1 atom.
Data collection: SMART (Siemens, 1996); cell refinement: SAINT (Siemens, 1996); data reduction: SAINT; program(s) used to solve structure: SHELXTL (Sheldrick, 1997); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL and PLATON (Spek, 1990).
Fig. 1. The molecular structure of (I) showing 50% probability displacement ellipsoids and the atom-numbering scheme; the butane solvent molecule has been omitted for clarity. |
[Au(C7H14NS2)(C18H15P)2]·C4H10 | F(000) = 1936 |
Mr = 955.94 | Dx = 1.376 Mg m−3 |
Monoclinic, P21/c | Mo Kα radiation, λ = 0.71073 Å |
a = 12.0927 (2) Å | Cell parameters from 8192 reflections |
b = 25.2129 (5) Å | θ = 1.6–28.4° |
c = 15.4999 (3) Å | µ = 3.38 mm−1 |
β = 102.392 (1)° | T = 293 K |
V = 4615.70 (15) Å3 | Slab, colourless |
Z = 4 | 0.42 × 0.28 × 0.12 mm |
Siemens SMART CCD area-detector diffractometer | 11360 independent reflections |
Radiation source: fine-focus sealed tube | 5735 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.072 |
Detector resolution: 8.33 pixels mm-1 | θmax = 28.3°, θmin = 1.6° |
ω scans | h = −16→16 |
Absorption correction: empirical (using intensity measurements) (SADABS; Sheldrick, 1996) | k = −29→33 |
Tmin = 0.331, Tmax = 0.687 | l = −20→17 |
31290 measured reflections |
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)] = 0.052 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.119 | H-atom parameters constrained |
S = 0.99 | w = 1/[σ2(Fo2) + (0.0331P)2] where P = (Fo2 + 2Fc2)/3 |
11360 reflections | (Δ/σ)max = 0.001 |
478 parameters | Δρmax = 1.31 e Å−3 |
3 restraints | Δρmin = −1.46 e Å−3 |
[Au(C7H14NS2)(C18H15P)2]·C4H10 | V = 4615.70 (15) Å3 |
Mr = 955.94 | Z = 4 |
Monoclinic, P21/c | Mo Kα radiation |
a = 12.0927 (2) Å | µ = 3.38 mm−1 |
b = 25.2129 (5) Å | T = 293 K |
c = 15.4999 (3) Å | 0.42 × 0.28 × 0.12 mm |
β = 102.392 (1)° |
Siemens SMART CCD area-detector diffractometer | 11360 independent reflections |
Absorption correction: empirical (using intensity measurements) (SADABS; Sheldrick, 1996) | 5735 reflections with I > 2σ(I) |
Tmin = 0.331, Tmax = 0.687 | Rint = 0.072 |
31290 measured reflections |
R[F2 > 2σ(F2)] = 0.052 | 3 restraints |
wR(F2) = 0.119 | H-atom parameters constrained |
S = 0.99 | Δρmax = 1.31 e Å−3 |
11360 reflections | Δρmin = −1.46 e Å−3 |
478 parameters |
Experimental. The data collection covered over a hemisphere of reciprocal space by a combination of three sets of exposures; each set had a different ϕ angle (0, 88 and 180°) for the crystal and each exposure of 10 s covered 0.3° in ω. The crystal-to-detector distance was 4 cm and the detector swing angle was −35°. Coverage of the unique set is over 99% complete. Crystal decay was monitored by repeating fifty initial frames at the end of data collection and analysing the duplicate reflections, and was found to be negligible. |
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 | ||
Au1 | 0.003638 (19) | 0.041403 (9) | 0.754681 (16) | 0.04747 (9) | |
S1 | −0.00648 (15) | 0.12619 (7) | 0.64886 (10) | 0.0543 (4) | |
P1 | 0.18396 (12) | 0.00391 (6) | 0.79054 (10) | 0.0392 (4) | |
S2 | 0.00540 (15) | 0.13589 (7) | 0.83879 (10) | 0.0528 (5) | |
P2 | −0.17678 (12) | 0.00387 (6) | 0.72036 (10) | 0.0401 (4) | |
N1 | −0.0321 (6) | 0.2182 (2) | 0.7266 (4) | 0.0699 (18) | |
C1 | 0.3029 (4) | 0.0492 (2) | 0.8271 (4) | 0.0409 (14) | |
C2 | 0.2899 (5) | 0.1012 (3) | 0.7975 (5) | 0.059 (2) | |
H2A | 0.2220 | 0.1126 | 0.7620 | 0.071* | |
C3 | 0.3798 (6) | 0.1358 (3) | 0.8218 (6) | 0.082 (3) | |
H3A | 0.3724 | 0.1704 | 0.8004 | 0.099* | |
C4 | 0.4798 (6) | 0.1206 (3) | 0.8766 (5) | 0.078 (2) | |
H4A | 0.5384 | 0.1449 | 0.8937 | 0.094* | |
C5 | 0.4918 (5) | 0.0695 (3) | 0.9057 (4) | 0.062 (2) | |
H5A | 0.5595 | 0.0586 | 0.9419 | 0.075* | |
C6 | 0.4038 (5) | 0.0337 (3) | 0.8817 (4) | 0.0528 (18) | |
H6A | 0.4125 | −0.0010 | 0.9025 | 0.063* | |
C7 | 0.1994 (4) | −0.0451 (2) | 0.8783 (3) | 0.0396 (14) | |
C8 | 0.1533 (5) | −0.0340 (3) | 0.9518 (4) | 0.0556 (18) | |
H8A | 0.1177 | −0.0016 | 0.9552 | 0.067* | |
C9 | 0.1598 (6) | −0.0703 (3) | 1.0191 (4) | 0.065 (2) | |
H9A | 0.1310 | −0.0619 | 1.0685 | 0.078* | |
C10 | 0.2085 (6) | −0.1186 (3) | 1.0131 (5) | 0.065 (2) | |
H10A | 0.2095 | −0.1438 | 1.0570 | 0.078* | |
C11 | 0.2558 (6) | −0.1299 (3) | 0.9430 (5) | 0.062 (2) | |
H11A | 0.2911 | −0.1624 | 0.9403 | 0.074* | |
C12 | 0.2517 (5) | −0.0937 (3) | 0.8762 (4) | 0.0525 (17) | |
H12A | 0.2847 | −0.1019 | 0.8289 | 0.063* | |
C13 | 0.2211 (5) | −0.0333 (2) | 0.7002 (3) | 0.0420 (15) | |
C14 | 0.3270 (6) | −0.0304 (3) | 0.6781 (4) | 0.064 (2) | |
H14A | 0.3835 | −0.0089 | 0.7102 | 0.076* | |
C15 | 0.3466 (7) | −0.0600 (3) | 0.6083 (5) | 0.086 (3) | |
H15A | 0.4181 | −0.0590 | 0.5952 | 0.103* | |
C16 | 0.2657 (7) | −0.0904 (3) | 0.5581 (5) | 0.070 (2) | |
H16A | 0.2808 | −0.1092 | 0.5104 | 0.084* | |
C17 | 0.1624 (7) | −0.0931 (3) | 0.5782 (4) | 0.063 (2) | |
H17A | 0.1066 | −0.1143 | 0.5445 | 0.076* | |
C18 | 0.1390 (5) | −0.0647 (2) | 0.6481 (4) | 0.0479 (16) | |
H18A | 0.0672 | −0.0666 | 0.6605 | 0.057* | |
C19 | −0.2133 (5) | −0.0350 (2) | 0.8098 (4) | 0.0446 (15) | |
C20 | −0.1309 (6) | −0.0676 (3) | 0.8591 (4) | 0.0574 (19) | |
H20A | −0.0594 | −0.0687 | 0.8460 | 0.069* | |
C21 | −0.1519 (7) | −0.0978 (3) | 0.9258 (5) | 0.067 (2) | |
H21A | −0.0951 | −0.1193 | 0.9577 | 0.080* | |
C22 | −0.2575 (8) | −0.0970 (3) | 0.9467 (5) | 0.081 (2) | |
H22A | −0.2722 | −0.1180 | 0.9922 | 0.097* | |
C23 | −0.3406 (7) | −0.0646 (3) | 0.8990 (5) | 0.081 (2) | |
H23A | −0.4113 | −0.0631 | 0.9134 | 0.097* | |
C24 | −0.3198 (6) | −0.0344 (3) | 0.8302 (5) | 0.064 (2) | |
H24A | −0.3771 | −0.0136 | 0.7973 | 0.077* | |
C25 | −0.1921 (5) | −0.0428 (3) | 0.6280 (4) | 0.0449 (15) | |
C26 | −0.2467 (5) | −0.0913 (3) | 0.6272 (4) | 0.0560 (18) | |
H26A | −0.2761 | −0.1018 | 0.6752 | 0.067* | |
C27 | −0.2570 (6) | −0.1240 (3) | 0.5538 (5) | 0.071 (2) | |
H27A | −0.2945 | −0.1563 | 0.5525 | 0.085* | |
C28 | −0.2129 (6) | −0.1092 (3) | 0.4840 (5) | 0.069 (2) | |
H28A | −0.2202 | −0.1316 | 0.4354 | 0.083* | |
C29 | −0.1578 (6) | −0.0619 (3) | 0.4845 (5) | 0.070 (2) | |
H29A | −0.1274 | −0.0522 | 0.4365 | 0.084* | |
C30 | −0.1476 (5) | −0.0287 (3) | 0.5565 (4) | 0.0565 (19) | |
H30A | −0.1103 | 0.0036 | 0.5568 | 0.068* | |
C31 | −0.2970 (4) | 0.0490 (3) | 0.6849 (4) | 0.0442 (15) | |
C32 | −0.3944 (5) | 0.0327 (3) | 0.6263 (4) | 0.059 (2) | |
H32A | −0.4000 | −0.0017 | 0.6039 | 0.070* | |
C33 | −0.4836 (5) | 0.0680 (3) | 0.6013 (5) | 0.070 (2) | |
H33A | −0.5495 | 0.0571 | 0.5627 | 0.084* | |
C34 | −0.4752 (6) | 0.1182 (3) | 0.6326 (5) | 0.075 (2) | |
H34A | −0.5348 | 0.1418 | 0.6150 | 0.090* | |
C35 | −0.3778 (6) | 0.1343 (3) | 0.6909 (6) | 0.085 (3) | |
H35A | −0.3718 | 0.1688 | 0.7125 | 0.102* | |
C36 | −0.2888 (5) | 0.0989 (3) | 0.7171 (5) | 0.062 (2) | |
H36A | −0.2236 | 0.1096 | 0.7568 | 0.074* | |
C37 | −0.0132 (5) | 0.1656 (2) | 0.7370 (4) | 0.0462 (14) | |
C38 | −0.0400 (8) | 0.2519 (3) | 0.8044 (6) | 0.091 (3) | |
H38A | −0.0208 | 0.2293 | 0.8569 | 0.110* | |
C39 | −0.1631 (10) | 0.2713 (4) | 0.7974 (7) | 0.149 (5) | |
H39A | −0.2134 | 0.2414 | 0.7900 | 0.223* | |
H39B | −0.1841 | 0.2946 | 0.7475 | 0.223* | |
H39C | −0.1683 | 0.2901 | 0.8503 | 0.223* | |
C40 | 0.0455 (11) | 0.2953 (5) | 0.8157 (9) | 0.191 (7) | |
H40A | 0.1194 | 0.2805 | 0.8188 | 0.286* | |
H40B | 0.0447 | 0.3143 | 0.8693 | 0.286* | |
H40C | 0.0275 | 0.3192 | 0.7664 | 0.286* | |
C41 | −0.0563 (10) | 0.2465 (3) | 0.6379 (6) | 0.103 (3) | |
H41A | −0.0720 | 0.2832 | 0.6519 | 0.124* | |
C42 | −0.1649 (11) | 0.2276 (4) | 0.5767 (7) | 0.150 (5) | |
H42A | −0.2252 | 0.2273 | 0.6081 | 0.225* | |
H42B | −0.1540 | 0.1924 | 0.5564 | 0.225* | |
H42C | −0.1840 | 0.2511 | 0.5270 | 0.225* | |
C43 | 0.0498 (11) | 0.2500 (5) | 0.5996 (9) | 0.180 (6) | |
H43A | 0.1121 | 0.2625 | 0.6443 | 0.270* | |
H43B | 0.0366 | 0.2742 | 0.5507 | 0.270* | |
H43C | 0.0673 | 0.2155 | 0.5799 | 0.270* | |
C44 | 0.400 (3) | 0.2662 (13) | 0.608 (4) | 0.77 (6) | |
H44A | 0.4235 | 0.2531 | 0.5571 | 1.156* | |
H44B | 0.3339 | 0.2880 | 0.5905 | 1.156* | |
H44C | 0.3825 | 0.2369 | 0.6428 | 1.156* | |
C45 | 0.493 (3) | 0.2985 (14) | 0.663 (2) | 0.70 (8) | |
H45A | 0.5680 | 0.2856 | 0.6599 | 0.838* | |
H45B | 0.4870 | 0.3360 | 0.6487 | 0.838* | |
C46 | 0.464 (3) | 0.2864 (10) | 0.750 (2) | 0.51 (4) | |
H46A | 0.3928 | 0.3051 | 0.7473 | 0.610* | |
H46B | 0.4437 | 0.2491 | 0.7458 | 0.610* | |
C47 | 0.526 (3) | 0.2931 (14) | 0.844 (2) | 0.57 (5) | |
H47A | 0.4738 | 0.3050 | 0.8792 | 0.861* | |
H47B | 0.5849 | 0.3188 | 0.8471 | 0.861* | |
H47C | 0.5578 | 0.2597 | 0.8667 | 0.861* |
U11 | U22 | U33 | U12 | U13 | U23 | |
Au1 | 0.03530 (12) | 0.05104 (14) | 0.05533 (15) | 0.00186 (16) | 0.00807 (9) | 0.00294 (16) |
S1 | 0.0754 (11) | 0.0544 (11) | 0.0364 (8) | 0.0114 (9) | 0.0191 (8) | 0.0003 (7) |
P1 | 0.0333 (8) | 0.0467 (10) | 0.0376 (8) | −0.0003 (7) | 0.0077 (7) | 0.0002 (7) |
S2 | 0.0632 (10) | 0.0611 (12) | 0.0354 (8) | 0.0000 (8) | 0.0133 (8) | −0.0041 (7) |
P2 | 0.0317 (8) | 0.0478 (10) | 0.0412 (9) | 0.0035 (7) | 0.0085 (7) | 0.0030 (7) |
N1 | 0.115 (5) | 0.055 (4) | 0.040 (3) | 0.006 (3) | 0.018 (3) | −0.002 (3) |
C1 | 0.036 (3) | 0.045 (4) | 0.044 (3) | −0.006 (3) | 0.014 (3) | −0.003 (3) |
C2 | 0.042 (4) | 0.057 (5) | 0.074 (5) | −0.015 (3) | 0.006 (4) | 0.008 (3) |
C3 | 0.069 (5) | 0.058 (6) | 0.116 (7) | −0.013 (4) | 0.009 (5) | 0.020 (4) |
C4 | 0.059 (5) | 0.079 (6) | 0.091 (6) | −0.033 (5) | 0.005 (5) | −0.005 (5) |
C5 | 0.042 (4) | 0.079 (6) | 0.062 (4) | −0.021 (4) | 0.002 (3) | 0.002 (4) |
C6 | 0.041 (3) | 0.063 (5) | 0.051 (4) | −0.002 (3) | 0.003 (3) | 0.005 (3) |
C7 | 0.031 (3) | 0.049 (4) | 0.040 (3) | −0.011 (3) | 0.009 (3) | 0.002 (3) |
C8 | 0.049 (4) | 0.063 (5) | 0.057 (4) | 0.000 (3) | 0.017 (3) | −0.005 (4) |
C9 | 0.066 (5) | 0.095 (6) | 0.035 (4) | −0.018 (4) | 0.015 (3) | 0.009 (4) |
C10 | 0.066 (5) | 0.065 (5) | 0.058 (5) | −0.018 (4) | 0.001 (4) | 0.020 (4) |
C11 | 0.072 (5) | 0.047 (5) | 0.064 (5) | 0.000 (3) | 0.012 (4) | 0.008 (4) |
C12 | 0.050 (4) | 0.060 (5) | 0.049 (4) | 0.000 (3) | 0.014 (3) | −0.002 (3) |
C13 | 0.047 (3) | 0.046 (4) | 0.032 (3) | 0.005 (3) | 0.009 (3) | 0.006 (3) |
C14 | 0.047 (4) | 0.088 (6) | 0.061 (4) | −0.007 (4) | 0.023 (4) | −0.014 (4) |
C15 | 0.078 (5) | 0.119 (7) | 0.073 (5) | −0.008 (5) | 0.045 (5) | −0.020 (5) |
C16 | 0.094 (6) | 0.063 (5) | 0.061 (5) | −0.008 (5) | 0.036 (5) | −0.015 (4) |
C17 | 0.081 (5) | 0.062 (5) | 0.042 (4) | −0.001 (4) | 0.003 (4) | −0.003 (3) |
C18 | 0.049 (4) | 0.054 (4) | 0.042 (3) | 0.000 (3) | 0.011 (3) | 0.002 (3) |
C19 | 0.045 (3) | 0.051 (4) | 0.040 (3) | 0.004 (3) | 0.013 (3) | −0.001 (3) |
C20 | 0.060 (4) | 0.065 (5) | 0.046 (4) | 0.005 (4) | 0.010 (4) | 0.009 (3) |
C21 | 0.078 (5) | 0.066 (5) | 0.055 (4) | 0.003 (4) | 0.011 (4) | 0.012 (4) |
C22 | 0.110 (7) | 0.078 (6) | 0.059 (5) | −0.015 (5) | 0.029 (5) | 0.014 (4) |
C23 | 0.086 (6) | 0.092 (6) | 0.080 (6) | 0.000 (5) | 0.051 (5) | 0.015 (5) |
C24 | 0.061 (4) | 0.072 (5) | 0.064 (4) | 0.004 (4) | 0.021 (4) | 0.011 (4) |
C25 | 0.041 (3) | 0.052 (4) | 0.040 (3) | 0.003 (3) | 0.005 (3) | 0.007 (3) |
C26 | 0.064 (4) | 0.055 (4) | 0.052 (4) | −0.008 (4) | 0.018 (4) | −0.002 (3) |
C27 | 0.069 (5) | 0.074 (6) | 0.066 (5) | 0.000 (4) | 0.007 (5) | −0.020 (4) |
C28 | 0.067 (5) | 0.090 (6) | 0.047 (4) | 0.020 (5) | 0.004 (4) | −0.019 (4) |
C29 | 0.070 (5) | 0.095 (6) | 0.047 (4) | 0.016 (5) | 0.019 (4) | 0.009 (4) |
C30 | 0.062 (4) | 0.063 (5) | 0.046 (4) | 0.001 (4) | 0.017 (4) | −0.003 (3) |
C31 | 0.032 (3) | 0.051 (4) | 0.048 (3) | 0.005 (3) | 0.006 (3) | 0.006 (3) |
C32 | 0.041 (3) | 0.066 (5) | 0.064 (4) | 0.007 (3) | 0.001 (3) | −0.001 (4) |
C33 | 0.042 (4) | 0.092 (6) | 0.067 (5) | 0.005 (4) | −0.008 (4) | 0.003 (4) |
C34 | 0.051 (4) | 0.077 (6) | 0.094 (6) | 0.022 (4) | 0.011 (4) | 0.012 (5) |
C35 | 0.069 (5) | 0.063 (6) | 0.119 (7) | 0.020 (4) | 0.015 (5) | −0.005 (5) |
C36 | 0.051 (4) | 0.054 (5) | 0.079 (5) | −0.001 (4) | 0.010 (4) | −0.008 (4) |
C37 | 0.049 (3) | 0.049 (3) | 0.041 (4) | −0.007 (3) | 0.011 (3) | 0.001 (3) |
C38 | 0.137 (8) | 0.066 (5) | 0.069 (5) | 0.004 (6) | 0.016 (6) | −0.019 (4) |
C39 | 0.170 (11) | 0.138 (10) | 0.145 (10) | 0.029 (9) | 0.048 (9) | −0.056 (8) |
C40 | 0.198 (14) | 0.174 (13) | 0.204 (15) | −0.082 (10) | 0.051 (13) | −0.127 (11) |
C41 | 0.174 (10) | 0.046 (5) | 0.092 (7) | −0.002 (6) | 0.034 (7) | 0.005 (4) |
C42 | 0.221 (13) | 0.110 (8) | 0.093 (8) | 0.073 (9) | −0.022 (9) | 0.005 (6) |
C43 | 0.257 (16) | 0.125 (11) | 0.202 (14) | −0.028 (11) | 0.147 (13) | 0.037 (9) |
C44 | 0.36 (5) | 0.12 (2) | 0.87 (19) | 0.05 (3) | 0.09 (8) | 0.16 (5) |
C45 | 0.31 (5) | 0.29 (6) | 0.9 (2) | 0.08 (4) | 0.17 (9) | 0.46 (10) |
C46 | 0.46 (6) | 0.14 (2) | 0.82 (12) | −0.14 (3) | −0.09 (7) | 0.09 (4) |
C47 | 0.25 (3) | 0.52 (6) | 0.96 (11) | −0.19 (4) | 0.14 (5) | −0.41 (7) |
Au1—P1 | 2.3318 (15) | C14—C15 | 1.375 (10) |
Au1—P2 | 2.3324 (15) | C15—C16 | 1.350 (10) |
Au1—S1 | 2.6811 (17) | C16—C17 | 1.352 (10) |
Au1—S2 | 2.7136 (17) | C17—C18 | 1.378 (9) |
S1—C37 | 1.704 (6) | C19—C20 | 1.388 (8) |
P1—C7 | 1.817 (6) | C19—C24 | 1.390 (9) |
P1—C13 | 1.820 (6) | C20—C21 | 1.351 (9) |
P1—C1 | 1.829 (5) | C21—C22 | 1.383 (10) |
S2—C37 | 1.717 (6) | C22—C23 | 1.381 (10) |
P2—C19 | 1.828 (6) | C23—C24 | 1.376 (10) |
P2—C25 | 1.831 (6) | C25—C30 | 1.380 (8) |
P2—C31 | 1.835 (6) | C25—C26 | 1.389 (8) |
N1—C37 | 1.350 (7) | C26—C27 | 1.387 (9) |
N1—C38 | 1.495 (9) | C27—C28 | 1.357 (10) |
N1—C41 | 1.521 (10) | C28—C29 | 1.366 (10) |
C1—C6 | 1.384 (7) | C29—C30 | 1.380 (9) |
C1—C2 | 1.386 (8) | C31—C36 | 1.348 (8) |
C2—C3 | 1.381 (8) | C31—C32 | 1.387 (7) |
C3—C4 | 1.375 (9) | C32—C33 | 1.388 (8) |
C4—C5 | 1.363 (9) | C33—C34 | 1.351 (10) |
C5—C6 | 1.384 (8) | C34—C35 | 1.383 (9) |
C7—C12 | 1.382 (8) | C35—C36 | 1.390 (8) |
C7—C8 | 1.399 (8) | C38—C40 | 1.492 (12) |
C8—C9 | 1.378 (9) | C38—C39 | 1.549 (12) |
C9—C10 | 1.364 (9) | C41—C42 | 1.523 (12) |
C10—C11 | 1.362 (10) | C41—C43 | 1.526 (13) |
C11—C12 | 1.373 (8) | C44—C45 | 1.500 (2) |
C13—C18 | 1.385 (8) | C45—C46 | 1.500 (2) |
C13—C14 | 1.397 (8) | C46—C47 | 1.500 (2) |
P1—Au1—P2 | 132.15 (5) | C14—C13—P1 | 123.5 (5) |
P1—Au1—S1 | 112.74 (6) | C15—C14—C13 | 119.1 (7) |
P2—Au1—S1 | 105.44 (5) | C16—C15—C14 | 122.3 (8) |
P1—Au1—S2 | 109.32 (5) | C15—C16—C17 | 119.1 (7) |
P2—Au1—S2 | 112.10 (6) | C16—C17—C18 | 120.7 (7) |
S1—Au1—S2 | 65.71 (5) | C17—C18—C13 | 120.8 (6) |
C37—S1—Au1 | 88.7 (2) | C20—C19—C24 | 118.2 (6) |
C7—P1—C13 | 102.9 (3) | C20—C19—P2 | 118.3 (5) |
C7—P1—C1 | 104.2 (2) | C24—C19—P2 | 123.6 (5) |
C13—P1—C1 | 104.6 (3) | C21—C20—C19 | 121.6 (7) |
C7—P1—Au1 | 113.24 (19) | C20—C21—C22 | 120.4 (7) |
C13—P1—Au1 | 113.46 (18) | C23—C22—C21 | 119.1 (7) |
C1—P1—Au1 | 117.0 (2) | C24—C23—C22 | 120.6 (8) |
C37—S2—Au1 | 87.4 (2) | C23—C24—C19 | 120.1 (7) |
C19—P2—C25 | 104.3 (3) | C30—C25—C26 | 119.1 (6) |
C19—P2—C31 | 104.8 (3) | C30—C25—P2 | 118.1 (5) |
C25—P2—C31 | 102.9 (3) | C26—C25—P2 | 122.8 (5) |
C19—P2—Au1 | 114.28 (18) | C27—C26—C25 | 119.3 (7) |
C25—P2—Au1 | 111.8 (2) | C28—C27—C26 | 120.7 (8) |
C31—P2—Au1 | 117.3 (2) | C27—C28—C29 | 120.6 (7) |
C37—N1—C38 | 120.0 (6) | C28—C29—C30 | 119.6 (7) |
C37—N1—C41 | 124.3 (6) | C25—C30—C29 | 120.7 (7) |
C38—N1—C41 | 115.4 (6) | C36—C31—C32 | 120.2 (6) |
C6—C1—C2 | 119.5 (5) | C36—C31—P2 | 118.5 (4) |
C6—C1—P1 | 122.9 (5) | C32—C31—P2 | 121.3 (5) |
C2—C1—P1 | 117.5 (4) | C31—C32—C33 | 119.5 (6) |
C3—C2—C1 | 118.7 (6) | C34—C33—C32 | 120.5 (6) |
C4—C3—C2 | 121.9 (7) | C33—C34—C35 | 119.8 (7) |
C5—C4—C3 | 118.9 (6) | C34—C35—C36 | 120.0 (7) |
C4—C5—C6 | 120.5 (6) | C31—C36—C35 | 120.0 (6) |
C1—C6—C5 | 120.3 (6) | N1—C37—S1 | 120.8 (5) |
C12—C7—C8 | 117.5 (6) | N1—C37—S2 | 121.5 (5) |
C12—C7—P1 | 124.0 (5) | S1—C37—S2 | 117.6 (3) |
C8—C7—P1 | 118.6 (5) | C40—C38—N1 | 110.5 (9) |
C9—C8—C7 | 121.0 (7) | C40—C38—C39 | 114.0 (9) |
C10—C9—C8 | 119.7 (7) | N1—C38—C39 | 110.5 (7) |
C11—C10—C9 | 120.2 (7) | N1—C41—C42 | 112.9 (8) |
C10—C11—C12 | 120.6 (7) | N1—C41—C43 | 111.3 (9) |
C11—C12—C7 | 120.9 (7) | C42—C41—C43 | 117.4 (10) |
C18—C13—C14 | 117.8 (6) | C46—C45—C44 | 96 (5) |
C18—C13—P1 | 118.6 (5) | C47—C46—C45 | 133 (3) |
Experimental details
Crystal data | |
Chemical formula | [Au(C7H14NS2)(C18H15P)2]·C4H10 |
Mr | 955.94 |
Crystal system, space group | Monoclinic, P21/c |
Temperature (K) | 293 |
a, b, c (Å) | 12.0927 (2), 25.2129 (5), 15.4999 (3) |
β (°) | 102.392 (1) |
V (Å3) | 4615.70 (15) |
Z | 4 |
Radiation type | Mo Kα |
µ (mm−1) | 3.38 |
Crystal size (mm) | 0.42 × 0.28 × 0.12 |
Data collection | |
Diffractometer | Siemens SMART CCD area-detector diffractometer |
Absorption correction | Empirical (using intensity measurements) (SADABS; Sheldrick, 1996) |
Tmin, Tmax | 0.331, 0.687 |
No. of measured, independent and observed [I > 2σ(I)] reflections | 31290, 11360, 5735 |
Rint | 0.072 |
(sin θ/λ)max (Å−1) | 0.666 |
Refinement | |
R[F2 > 2σ(F2)], wR(F2), S | 0.052, 0.119, 0.99 |
No. of reflections | 11360 |
No. of parameters | 478 |
No. of restraints | 3 |
H-atom treatment | H-atom parameters constrained |
Δρmax, Δρmin (e Å−3) | 1.31, −1.46 |
Computer programs: SMART (Siemens, 1996), SAINT (Siemens, 1996), SAINT, SHELXTL (Sheldrick, 1997), SHELXTL and PLATON (Spek, 1990).
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There has been growing interest in the study of d10 metal complexes, which exhibit rich photophysical and photochemical properties (Harvey & Gray, 1988; Vogler & Kunkely, 1988). Of particular interest is the nature of the lowest electronic excited states, which serve to develop a better understanding of the luminescent properties of d10–d10 systems (Yam et al., 1990). Also, it has been found that gold(I) dialkyldithiocarbamates exist in discrete dimeric units which stack in the solid state to form linear gold chains (Hesse & Jennische, 1972). The number of gold(I) complexes of this type is limited in the literature. As part of our work on this type of complex, we present here the synthesis and crystal structure of the novel gold(I) complex (N,N-diisopropyldithiocarbamato-S,S')bis(triphenylphosphine-P)gold(I) butane solvate, (I).
The crystal structure of (I) consists of mononuclear [Au(PPh3)2{S2CN(iPr)2}] units and butane molecules in a 1:1 ratio. As shown in Fig. 1, the AuI ion in (I) is four-coordinated forming a distorted tetrahedron. The diisopropyldithiocarbamate ligand acts as a bidentate ligand coordinating through the two S atoms, forming a four-membered chelate ring. The other positions of the tetrahedron are occupied by two triphenylphosphine ligands.
The four-membered AuS2C ring is planar, with a maximum deviation of 0.047 (6) Å for C37. The Au1—S2 bond length [2.714 (2) Å] is longer than that of Au1—S1 [2.681 (2) Å] as the former is a coordination bond. Only a small variation in the C—S bond distance is observed. The Au—P distances are almost equal and are slightly longer than those found in [(AuSC2H4PEt2)2 [2.27 (2) Å; Crane & Beall, 1978] and C14H38Au3Cl3O12P6·2.5H2O [2.296 (7) Å; Yam et al., 1990]. The C37—N1 distance [1.350 (7) Å] has double-bond character, but is a little longer than those observed in the related structures (Sharma et al., 1991; Gimeno et al., 1996; Jian et al., 1999). The P—C and C—C bond distances are in good agreement with values reported for silimar structures (Zheng et al., 1997; Razak et al., 2000).
The smallest angle, S1—Au1—S2 of 65.71 (5)°, is restricted by the bite angle of the ligand (Crespo et al., 1997; Jones et al., 1994; Gimeno et al., 1994), whereas the largest alngle, P1—Au1—P2 of 132.15 (5)°, is the open side opposite the chelate ring. A possible explanation for this large value is minimization of the steric interaction between the PPh3 groups. The other P—Au—S angles deviate slightly from the tetrahedral value of 109.47°.
A non-crystallographic twofold axis passes through atoms N1, C17 and Au1. The diisopropyl group is twisted by 7.5 (2)° with respect to the AuS2C group. The isopropyl groups are at anticlinal (C38, C39 and C40) and synclinal (C41, C42 and C43) orientations with respect to the N1—C38 and N1—C41 bonds, respectively. The N1—C37 bond act as an ethylene bond with S atoms and isopropyl groups on either side. The orientations of the isopropyl groups are limited by the intramolecular C—S interaction. The butane solvent is not involved in any interaction as there is no potential acceptor atom.
It is quite interesting to note that the molecular structure is stabilized by intramolecular C—H···π interaction between the aromatic H atoms of the PPh3 groups and the centroid (Cg) of the chelate ring (atoms Au1, S1, C37 and S2) [C2···Cg = 3.48, H2A···Cg = 2.68 Å, C2—H2A···Cg = 145°; C36···Cg = 3.43, H36A···Cg = 2.72 Å, C36—H36A···Cg = 133°;].