
Acta Cryst. (2010). E66, m420 [ doi:10.1107/S1600536810009736 ]
S](tricyclohexylphosphine-
P)gold(I)The Au atom in the title compound, [Au(C10H11ClNOS)(C18H33P)], is coordinated within an S,P-donor set that defines a slightly distorted linear geometry [S-Au-P = 172.45 (5)°], with the distortion due in part to a close intramolecular Au
O contact [3.134 (3) Å].
Compound (I) was prepared following the standard literature procedure from the reaction of Cy3PAuCl and (i-Pr)OC(═S)N(H)(C6H4Cl-4) in the presence of NaOH (Hall et al., 1993). Crystals were obtained by the slow evaporation of a CH2Cl2/hexane (3/1) solution held at room temperature.
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 3.49 and 1.06 e Å-3, respectively, were located 0.85 Å and 0.70 Å from the Au atom.
Data collection: SMART (Bruker, 2000); cell refinement: 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: ORTEP-3 (Farrugia, 1997) and DIAMOND (Brandenburg, 2006); software used to prepare material for publication: publCIF (Westrip, 2010).
| Fig. 1. Molecular structure of (I) showing atom-labelling scheme and displacement ellipsoids at the 35% probability level. |
| [Au(C10H11ClNOS)(C18H33P)] | F(000) = 1416 |
| Mr = 706.09 | Dx = 1.564 Mg m−3 |
| Monoclinic, P21/c | Mo Kα radiation, λ = 0.71069 Å |
| Hall symbol: -P 2ybc | Cell parameters from 879 reflections |
| a = 9.4547 (15) Å | θ = 2.6–27.4° |
| b = 26.137 (4) Å | µ = 5.14 mm−1 |
| c = 12.326 (2) Å | T = 223 K |
| β = 100.162 (3)° | Prism, colourless |
| V = 2998.0 (8) Å3 | 0.32 × 0.07 × 0.07 mm |
| Z = 4 |
| Bruker SMART CCD diffractometer | 6886 independent reflections |
| Radiation source: fine-focus sealed tube | 5416 reflections with I > 2σ(I) |
| graphite | Rint = 0.037 |
| ω scans | θmax = 27.5°, θmin = 1.9° |
| Absorption correction: multi-scan (SADABS; Bruker, 2000) | h = −12→9 |
| Tmin = 0.466, Tmax = 1.000 | k = −33→33 |
| 20961 measured reflections | l = −15→15 |
| 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)] = 0.039 | Hydrogen site location: inferred from neighbouring sites |
| wR(F2) = 0.087 | H-atom parameters constrained |
| S = 1.06 | w = 1/[σ2(Fo2) + (0.0354P)2 + 3.2652P] where P = (Fo2 + 2Fc2)/3 |
| 6886 reflections | (Δ/σ)max = 0.001 |
| 307 parameters | Δρmax = 3.49 e Å−3 |
| 0 restraints | Δρmin = −1.06 e Å−3 |
| [Au(C10H11ClNOS)(C18H33P)] | V = 2998.0 (8) Å3 |
| Mr = 706.09 | Z = 4 |
| Monoclinic, P21/c | Mo Kα radiation |
| a = 9.4547 (15) Å | µ = 5.14 mm−1 |
| b = 26.137 (4) Å | T = 223 K |
| c = 12.326 (2) Å | 0.32 × 0.07 × 0.07 mm |
| β = 100.162 (3)° |
| Bruker SMART CCD diffractometer | 6886 independent reflections |
| Absorption correction: multi-scan (SADABS; Bruker, 2000) | 5416 reflections with I > 2σ(I) |
| Tmin = 0.466, Tmax = 1.000 | Rint = 0.037 |
| 20961 measured reflections | θmax = 27.5° |
| R[F2 > 2σ(F2)] = 0.039 | H-atom parameters constrained |
| wR(F2) = 0.087 | Δρmax = 3.49 e Å−3 |
| S = 1.06 | Δρmin = −1.06 e Å−3 |
| 6886 reflections | Absolute structure: ? |
| 307 parameters | Flack parameter: ? |
| 0 restraints | Rogers parameter: ? |
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 | 0.11172 (2) | 0.032224 (6) | 0.326336 (15) | 0.03900 (7) | |
| Cl1 | −0.41157 (16) | 0.29686 (6) | 0.41611 (13) | 0.0629 (4) | |
| S1 | 0.04148 (19) | 0.11519 (5) | 0.35057 (11) | 0.0547 (4) | |
| P1 | 0.16119 (15) | −0.05231 (5) | 0.31795 (10) | 0.0361 (3) | |
| O1 | 0.1788 (4) | 0.12683 (12) | 0.1876 (3) | 0.0391 (8) | |
| N1 | 0.0218 (5) | 0.19166 (14) | 0.2031 (3) | 0.0398 (9) | |
| C1 | 0.0788 (5) | 0.14992 (17) | 0.2375 (4) | 0.0360 (10) | |
| C2 | −0.0798 (5) | 0.21535 (17) | 0.2577 (4) | 0.0365 (11) | |
| C3 | −0.0419 (6) | 0.23739 (19) | 0.3612 (4) | 0.0445 (12) | |
| H3 | 0.0537 | 0.2351 | 0.3982 | 0.053* | |
| C4 | −0.1416 (6) | 0.26265 (19) | 0.4109 (4) | 0.0431 (12) | |
| H4 | −0.1149 | 0.2771 | 0.4813 | 0.052* | |
| C5 | −0.2805 (5) | 0.26620 (17) | 0.3554 (4) | 0.0396 (11) | |
| C6 | −0.3205 (6) | 0.2456 (2) | 0.2522 (4) | 0.0478 (13) | |
| H6 | −0.4157 | 0.2487 | 0.2147 | 0.057* | |
| C7 | −0.2198 (6) | 0.2204 (2) | 0.2044 (4) | 0.0468 (12) | |
| H7 | −0.2470 | 0.2063 | 0.1336 | 0.056* | |
| C8 | 0.2135 (6) | 0.1506 (2) | 0.0885 (4) | 0.0443 (12) | |
| H8 | 0.1240 | 0.1610 | 0.0390 | 0.053* | |
| C9 | 0.3096 (7) | 0.1964 (2) | 0.1161 (6) | 0.0720 (19) | |
| H9A | 0.2581 | 0.2229 | 0.1483 | 0.108* | |
| H9B | 0.3382 | 0.2093 | 0.0494 | 0.108* | |
| H9C | 0.3943 | 0.1865 | 0.1683 | 0.108* | |
| C10 | 0.2859 (7) | 0.1079 (2) | 0.0358 (5) | 0.0570 (15) | |
| H10A | 0.2191 | 0.0798 | 0.0177 | 0.085* | |
| H10B | 0.3696 | 0.0962 | 0.0869 | 0.085* | |
| H10C | 0.3153 | 0.1205 | −0.0309 | 0.085* | |
| C11 | 0.2157 (5) | −0.07089 (17) | 0.1873 (4) | 0.0357 (10) | |
| H11 | 0.2373 | −0.1080 | 0.1898 | 0.043* | |
| C12 | 0.3503 (6) | −0.0418 (2) | 0.1728 (4) | 0.0467 (13) | |
| H12A | 0.4278 | −0.0496 | 0.2346 | 0.056* | |
| H12B | 0.3313 | −0.0049 | 0.1739 | 0.056* | |
| C13 | 0.3983 (7) | −0.0558 (2) | 0.0650 (5) | 0.0594 (16) | |
| H13A | 0.4813 | −0.0347 | 0.0562 | 0.071* | |
| H13B | 0.4286 | −0.0917 | 0.0678 | 0.071* | |
| C14 | 0.2799 (8) | −0.0479 (2) | −0.0335 (5) | 0.0689 (19) | |
| H14A | 0.3116 | −0.0610 | −0.0998 | 0.083* | |
| H14B | 0.2610 | −0.0112 | −0.0438 | 0.083* | |
| C15 | 0.1423 (7) | −0.0750 (2) | −0.0190 (5) | 0.0618 (16) | |
| H15A | 0.0655 | −0.0660 | −0.0804 | 0.074* | |
| H15B | 0.1569 | −0.1121 | −0.0206 | 0.074* | |
| C16 | 0.0970 (6) | −0.0603 (2) | 0.0886 (4) | 0.0496 (13) | |
| H16A | 0.0108 | −0.0797 | 0.0970 | 0.059* | |
| H16B | 0.0725 | −0.0239 | 0.0870 | 0.059* | |
| C17 | 0.3117 (6) | −0.07052 (19) | 0.4301 (4) | 0.0465 (12) | |
| H17 | 0.3989 | −0.0554 | 0.4090 | 0.056* | |
| C18 | 0.2971 (7) | −0.0452 (2) | 0.5377 (5) | 0.0554 (14) | |
| H18A | 0.2907 | −0.0081 | 0.5271 | 0.066* | |
| H18B | 0.2080 | −0.0568 | 0.5602 | 0.066* | |
| C19 | 0.4528 (8) | −0.1131 (3) | 0.6415 (7) | 0.083 (2) | |
| H19A | 0.5414 | −0.1180 | 0.6953 | 0.100* | |
| H19B | 0.3744 | −0.1298 | 0.6706 | 0.100* | |
| C20 | 0.4219 (8) | −0.0573 (3) | 0.6277 (5) | 0.0724 (19) | |
| H20A | 0.5077 | −0.0400 | 0.6114 | 0.087* | |
| H20B | 0.4020 | −0.0435 | 0.6974 | 0.087* | |
| C21 | 0.4688 (8) | −0.1377 (3) | 0.5361 (6) | 0.079 (2) | |
| H21A | 0.4788 | −0.1747 | 0.5475 | 0.095* | |
| H21B | 0.5573 | −0.1252 | 0.5141 | 0.095* | |
| C22 | 0.3425 (6) | −0.1274 (2) | 0.4425 (5) | 0.0572 (15) | |
| H22A | 0.3649 | −0.1410 | 0.3733 | 0.069* | |
| H22B | 0.2569 | −0.1452 | 0.4579 | 0.069* | |
| C23 | 0.0073 (6) | −0.09140 (18) | 0.3403 (5) | 0.0458 (12) | |
| H23 | 0.0199 | −0.0958 | 0.4212 | 0.055* | |
| C24 | −0.0029 (6) | −0.14566 (19) | 0.2938 (5) | 0.0493 (13) | |
| H24A | −0.0203 | −0.1442 | 0.2131 | 0.059* | |
| H24B | 0.0883 | −0.1635 | 0.3182 | 0.059* | |
| C25 | −0.1236 (7) | −0.1750 (2) | 0.3320 (6) | 0.0714 (19) | |
| H25A | −0.1305 | −0.2090 | 0.2980 | 0.086* | |
| H25B | −0.0997 | −0.1797 | 0.4120 | 0.086* | |
| C26 | −0.2653 (7) | −0.1494 (2) | 0.3048 (6) | 0.0650 (17) | |
| H26A | −0.3351 | −0.1680 | 0.3401 | 0.078* | |
| H26B | −0.2985 | −0.1506 | 0.2249 | 0.078* | |
| C27 | −0.2580 (6) | −0.0941 (2) | 0.3430 (5) | 0.0571 (15) | |
| H27A | −0.3490 | −0.0772 | 0.3129 | 0.068* | |
| H27B | −0.2470 | −0.0933 | 0.4236 | 0.068* | |
| C28 | −0.1359 (6) | −0.0642 (2) | 0.3087 (5) | 0.0548 (14) | |
| H28A | −0.1299 | −0.0304 | 0.3437 | 0.066* | |
| H28B | −0.1561 | −0.0591 | 0.2287 | 0.066* |
| U11 | U22 | U33 | U12 | U13 | U23 | |
| Au | 0.05318 (13) | 0.02822 (10) | 0.03867 (11) | 0.00624 (9) | 0.01655 (8) | 0.00351 (8) |
| Cl1 | 0.0515 (9) | 0.0689 (9) | 0.0713 (10) | 0.0156 (7) | 0.0188 (7) | −0.0129 (8) |
| S1 | 0.0946 (12) | 0.0329 (6) | 0.0458 (7) | 0.0167 (7) | 0.0377 (8) | 0.0081 (5) |
| P1 | 0.0430 (7) | 0.0294 (6) | 0.0383 (7) | 0.0035 (5) | 0.0137 (6) | 0.0014 (5) |
| O1 | 0.046 (2) | 0.0363 (17) | 0.0385 (18) | 0.0048 (15) | 0.0171 (16) | 0.0017 (14) |
| N1 | 0.048 (3) | 0.036 (2) | 0.039 (2) | 0.0080 (18) | 0.0156 (19) | 0.0063 (17) |
| C1 | 0.044 (3) | 0.032 (2) | 0.034 (2) | −0.003 (2) | 0.012 (2) | 0.0011 (19) |
| C2 | 0.045 (3) | 0.030 (2) | 0.038 (3) | 0.003 (2) | 0.017 (2) | 0.0041 (19) |
| C3 | 0.040 (3) | 0.046 (3) | 0.046 (3) | 0.006 (2) | 0.002 (2) | 0.001 (2) |
| C4 | 0.046 (3) | 0.043 (3) | 0.040 (3) | 0.005 (2) | 0.008 (2) | −0.005 (2) |
| C5 | 0.038 (3) | 0.035 (2) | 0.047 (3) | 0.006 (2) | 0.013 (2) | −0.001 (2) |
| C6 | 0.040 (3) | 0.052 (3) | 0.050 (3) | 0.003 (2) | 0.006 (2) | 0.000 (2) |
| C7 | 0.048 (3) | 0.051 (3) | 0.041 (3) | −0.002 (2) | 0.008 (2) | −0.006 (2) |
| C8 | 0.046 (3) | 0.051 (3) | 0.039 (3) | 0.008 (2) | 0.017 (2) | 0.009 (2) |
| C9 | 0.069 (4) | 0.053 (4) | 0.105 (6) | −0.006 (3) | 0.044 (4) | 0.005 (4) |
| C10 | 0.058 (4) | 0.068 (4) | 0.049 (3) | 0.015 (3) | 0.022 (3) | −0.003 (3) |
| C11 | 0.038 (3) | 0.031 (2) | 0.040 (3) | 0.000 (2) | 0.015 (2) | −0.0033 (19) |
| C12 | 0.044 (3) | 0.050 (3) | 0.047 (3) | −0.004 (2) | 0.013 (3) | 0.004 (2) |
| C13 | 0.065 (4) | 0.052 (3) | 0.072 (4) | 0.002 (3) | 0.040 (4) | 0.005 (3) |
| C14 | 0.108 (6) | 0.057 (3) | 0.052 (4) | 0.001 (4) | 0.043 (4) | 0.003 (3) |
| C15 | 0.085 (5) | 0.062 (4) | 0.039 (3) | −0.014 (3) | 0.011 (3) | −0.009 (3) |
| C16 | 0.045 (3) | 0.063 (3) | 0.039 (3) | −0.005 (3) | 0.001 (2) | −0.004 (2) |
| C17 | 0.052 (3) | 0.042 (3) | 0.045 (3) | 0.006 (2) | 0.006 (2) | 0.007 (2) |
| C18 | 0.059 (4) | 0.052 (3) | 0.052 (3) | 0.003 (3) | 0.002 (3) | −0.003 (3) |
| C19 | 0.067 (5) | 0.096 (6) | 0.079 (5) | −0.004 (4) | −0.009 (4) | 0.029 (4) |
| C20 | 0.079 (5) | 0.088 (5) | 0.044 (3) | −0.014 (4) | −0.007 (3) | 0.010 (3) |
| C21 | 0.073 (5) | 0.076 (5) | 0.087 (5) | 0.027 (4) | 0.011 (4) | 0.035 (4) |
| C22 | 0.053 (4) | 0.040 (3) | 0.076 (4) | 0.004 (3) | 0.006 (3) | 0.002 (3) |
| C23 | 0.050 (3) | 0.036 (2) | 0.055 (3) | −0.001 (2) | 0.018 (3) | 0.000 (2) |
| C24 | 0.049 (3) | 0.039 (3) | 0.063 (4) | −0.005 (2) | 0.018 (3) | −0.009 (2) |
| C25 | 0.075 (5) | 0.046 (3) | 0.103 (6) | −0.011 (3) | 0.042 (4) | −0.004 (3) |
| C26 | 0.051 (4) | 0.076 (4) | 0.068 (4) | −0.020 (3) | 0.010 (3) | −0.010 (3) |
| C27 | 0.047 (3) | 0.059 (3) | 0.070 (4) | 0.010 (3) | 0.024 (3) | 0.009 (3) |
| C28 | 0.037 (3) | 0.049 (3) | 0.077 (4) | 0.000 (2) | 0.005 (3) | −0.004 (3) |
| Au—P1 | 2.2646 (12) | C14—H14B | 0.9800 |
| Au—S1 | 2.3027 (13) | C15—C16 | 1.514 (7) |
| Cl1—C5 | 1.751 (5) | C15—H15A | 0.9800 |
| S1—C1 | 1.750 (5) | C15—H15B | 0.9800 |
| P1—C23 | 1.838 (5) | C16—H16A | 0.9800 |
| P1—C11 | 1.840 (4) | C16—H16B | 0.9800 |
| P1—C17 | 1.862 (5) | C17—C18 | 1.511 (8) |
| O1—C1 | 1.356 (5) | C17—C22 | 1.518 (7) |
| O1—C8 | 1.459 (5) | C17—H17 | 0.9900 |
| N1—C1 | 1.257 (6) | C18—C20 | 1.503 (8) |
| N1—C2 | 1.410 (6) | C18—H18A | 0.9800 |
| C2—C7 | 1.376 (7) | C18—H18B | 0.9800 |
| C2—C3 | 1.388 (7) | C19—C21 | 1.481 (10) |
| C3—C4 | 1.380 (7) | C19—C20 | 1.492 (10) |
| C3—H3 | 0.9400 | C19—H19A | 0.9800 |
| C4—C5 | 1.373 (7) | C19—H19B | 0.9800 |
| C4—H4 | 0.9400 | C20—H20A | 0.9800 |
| C5—C6 | 1.371 (7) | C20—H20B | 0.9800 |
| C6—C7 | 1.374 (7) | C21—C22 | 1.531 (9) |
| C6—H6 | 0.9400 | C21—H21A | 0.9800 |
| C7—H7 | 0.9400 | C21—H21B | 0.9800 |
| C8—C9 | 1.505 (8) | C22—H22A | 0.9800 |
| C8—C10 | 1.514 (7) | C22—H22B | 0.9800 |
| C8—H8 | 0.9900 | C23—C28 | 1.518 (7) |
| C9—H9A | 0.9700 | C23—C24 | 1.526 (7) |
| C9—H9B | 0.9700 | C23—H23 | 0.9900 |
| C9—H9C | 0.9700 | C24—C25 | 1.516 (7) |
| C10—H10A | 0.9700 | C24—H24A | 0.9800 |
| C10—H10B | 0.9700 | C24—H24B | 0.9800 |
| C10—H10C | 0.9700 | C25—C26 | 1.481 (9) |
| C11—C12 | 1.520 (7) | C25—H25A | 0.9800 |
| C11—C16 | 1.528 (7) | C25—H25B | 0.9800 |
| C11—H11 | 0.9900 | C26—C27 | 1.519 (8) |
| C12—C13 | 1.524 (7) | C26—H26A | 0.9800 |
| C12—H12A | 0.9800 | C26—H26B | 0.9800 |
| C12—H12B | 0.9800 | C27—C28 | 1.514 (7) |
| C13—C14 | 1.513 (9) | C27—H27A | 0.9800 |
| C13—H13A | 0.9800 | C27—H27B | 0.9800 |
| C13—H13B | 0.9800 | C28—H28A | 0.9800 |
| C14—C15 | 1.519 (9) | C28—H28B | 0.9800 |
| C14—H14A | 0.9800 | ||
| P1—Au—S1 | 172.45 (5) | C15—C16—C11 | 111.7 (5) |
| C1—S1—Au | 106.36 (16) | C15—C16—H16A | 109.3 |
| C23—P1—C11 | 109.6 (2) | C11—C16—H16A | 109.3 |
| C23—P1—C17 | 105.6 (2) | C15—C16—H16B | 109.3 |
| C11—P1—C17 | 106.7 (2) | C11—C16—H16B | 109.3 |
| C23—P1—Au | 111.10 (16) | H16A—C16—H16B | 107.9 |
| C11—P1—Au | 112.92 (15) | C18—C17—C22 | 112.7 (5) |
| C17—P1—Au | 110.63 (17) | C18—C17—P1 | 111.3 (4) |
| C1—O1—C8 | 117.9 (4) | C22—C17—P1 | 115.7 (4) |
| C1—N1—C2 | 120.5 (4) | C18—C17—H17 | 105.4 |
| N1—C1—O1 | 121.7 (4) | C22—C17—H17 | 105.4 |
| N1—C1—S1 | 125.7 (4) | P1—C17—H17 | 105.4 |
| O1—C1—S1 | 112.6 (3) | C20—C18—C17 | 112.0 (5) |
| C7—C2—C3 | 118.0 (4) | C20—C18—H18A | 109.2 |
| C7—C2—N1 | 119.6 (4) | C17—C18—H18A | 109.2 |
| C3—C2—N1 | 122.2 (5) | C20—C18—H18B | 109.2 |
| C4—C3—C2 | 121.4 (5) | C17—C18—H18B | 109.2 |
| C4—C3—H3 | 119.3 | H18A—C18—H18B | 107.9 |
| C2—C3—H3 | 119.3 | C21—C19—C20 | 111.8 (6) |
| C5—C4—C3 | 118.7 (5) | C21—C19—H19A | 109.3 |
| C5—C4—H4 | 120.7 | C20—C19—H19A | 109.3 |
| C3—C4—H4 | 120.7 | C21—C19—H19B | 109.3 |
| C6—C5—C4 | 121.3 (5) | C20—C19—H19B | 109.3 |
| C6—C5—Cl1 | 118.4 (4) | H19A—C19—H19B | 107.9 |
| C4—C5—Cl1 | 120.4 (4) | C19—C20—C18 | 113.7 (6) |
| C5—C6—C7 | 119.2 (5) | C19—C20—H20A | 108.8 |
| C5—C6—H6 | 120.4 | C18—C20—H20A | 108.8 |
| C7—C6—H6 | 120.4 | C19—C20—H20B | 108.8 |
| C6—C7—C2 | 121.5 (5) | C18—C20—H20B | 108.8 |
| C6—C7—H7 | 119.3 | H20A—C20—H20B | 107.7 |
| C2—C7—H7 | 119.3 | C19—C21—C22 | 113.5 (6) |
| O1—C8—C9 | 111.5 (5) | C19—C21—H21A | 108.9 |
| O1—C8—C10 | 103.3 (4) | C22—C21—H21A | 108.9 |
| C9—C8—C10 | 112.5 (5) | C19—C21—H21B | 108.9 |
| O1—C8—H8 | 109.8 | C22—C21—H21B | 108.9 |
| C9—C8—H8 | 109.8 | H21A—C21—H21B | 107.7 |
| C10—C8—H8 | 109.8 | C17—C22—C21 | 111.0 (5) |
| C8—C9—H9A | 109.5 | C17—C22—H22A | 109.4 |
| C8—C9—H9B | 109.5 | C21—C22—H22A | 109.4 |
| H9A—C9—H9B | 109.5 | C17—C22—H22B | 109.4 |
| C8—C9—H9C | 109.5 | C21—C22—H22B | 109.4 |
| H9A—C9—H9C | 109.5 | H22A—C22—H22B | 108.0 |
| H9B—C9—H9C | 109.5 | C28—C23—C24 | 110.1 (5) |
| C8—C10—H10A | 109.5 | C28—C23—P1 | 113.3 (4) |
| C8—C10—H10B | 109.5 | C24—C23—P1 | 117.3 (4) |
| H10A—C10—H10B | 109.5 | C28—C23—H23 | 104.9 |
| C8—C10—H10C | 109.5 | C24—C23—H23 | 104.9 |
| H10A—C10—H10C | 109.5 | P1—C23—H23 | 104.9 |
| H10B—C10—H10C | 109.5 | C25—C24—C23 | 110.8 (4) |
| C12—C11—C16 | 109.2 (4) | C25—C24—H24A | 109.5 |
| C12—C11—P1 | 109.9 (3) | C23—C24—H24A | 109.5 |
| C16—C11—P1 | 111.7 (3) | C25—C24—H24B | 109.5 |
| C12—C11—H11 | 108.7 | C23—C24—H24B | 109.5 |
| C16—C11—H11 | 108.7 | H24A—C24—H24B | 108.1 |
| P1—C11—H11 | 108.7 | C26—C25—C24 | 113.7 (5) |
| C11—C12—C13 | 111.5 (4) | C26—C25—H25A | 108.8 |
| C11—C12—H12A | 109.3 | C24—C25—H25A | 108.8 |
| C13—C12—H12A | 109.3 | C26—C25—H25B | 108.8 |
| C11—C12—H12B | 109.3 | C24—C25—H25B | 108.8 |
| C13—C12—H12B | 109.3 | H25A—C25—H25B | 107.7 |
| H12A—C12—H12B | 108.0 | C25—C26—C27 | 111.7 (5) |
| C14—C13—C12 | 112.0 (5) | C25—C26—H26A | 109.3 |
| C14—C13—H13A | 109.2 | C27—C26—H26A | 109.3 |
| C12—C13—H13A | 109.2 | C25—C26—H26B | 109.3 |
| C14—C13—H13B | 109.2 | C27—C26—H26B | 109.3 |
| C12—C13—H13B | 109.2 | H26A—C26—H26B | 107.9 |
| H13A—C13—H13B | 107.9 | C28—C27—C26 | 113.6 (5) |
| C13—C14—C15 | 111.8 (5) | C28—C27—H27A | 108.9 |
| C13—C14—H14A | 109.3 | C26—C27—H27A | 108.9 |
| C15—C14—H14A | 109.3 | C28—C27—H27B | 108.9 |
| C13—C14—H14B | 109.3 | C26—C27—H27B | 108.9 |
| C15—C14—H14B | 109.3 | H27A—C27—H27B | 107.7 |
| H14A—C14—H14B | 107.9 | C27—C28—C23 | 112.1 (5) |
| C16—C15—C14 | 111.5 (5) | C27—C28—H28A | 109.2 |
| C16—C15—H15A | 109.3 | C23—C28—H28A | 109.2 |
| C14—C15—H15A | 109.3 | C27—C28—H28B | 109.2 |
| C16—C15—H15B | 109.3 | C23—C28—H28B | 109.2 |
| C14—C15—H15B | 109.3 | H28A—C28—H28B | 107.9 |
| H15A—C15—H15B | 108.0 | ||
| P1—Au—S1—C1 | −159.3 (4) | C12—C13—C14—C15 | −52.6 (7) |
| S1—Au—P1—C23 | 29.2 (5) | C13—C14—C15—C16 | 53.0 (7) |
| S1—Au—P1—C11 | 152.8 (4) | C14—C15—C16—C11 | −56.1 (7) |
| S1—Au—P1—C17 | −87.8 (5) | C12—C11—C16—C15 | 57.6 (6) |
| C2—N1—C1—O1 | −178.8 (4) | P1—C11—C16—C15 | 179.3 (4) |
| C2—N1—C1—S1 | 1.4 (7) | C23—P1—C17—C18 | −78.2 (4) |
| C8—O1—C1—N1 | −3.1 (7) | C11—P1—C17—C18 | 165.2 (4) |
| C8—O1—C1—S1 | 176.7 (3) | Au—P1—C17—C18 | 42.1 (4) |
| Au—S1—C1—N1 | 158.6 (4) | C23—P1—C17—C22 | 52.1 (5) |
| Au—S1—C1—O1 | −21.1 (4) | C11—P1—C17—C22 | −64.4 (5) |
| C1—N1—C2—C7 | −114.7 (6) | Au—P1—C17—C22 | 172.4 (4) |
| C1—N1—C2—C3 | 70.2 (6) | C22—C17—C18—C20 | 51.2 (7) |
| C7—C2—C3—C4 | 1.5 (7) | P1—C17—C18—C20 | −177.0 (4) |
| N1—C2—C3—C4 | 176.7 (4) | C21—C19—C20—C18 | 52.5 (9) |
| C2—C3—C4—C5 | −0.7 (8) | C17—C18—C20—C19 | −51.8 (8) |
| C3—C4—C5—C6 | −0.6 (8) | C20—C19—C21—C22 | −52.7 (8) |
| C3—C4—C5—Cl1 | 178.8 (4) | C18—C17—C22—C21 | −50.9 (7) |
| C4—C5—C6—C7 | 0.9 (8) | P1—C17—C22—C21 | 179.4 (4) |
| Cl1—C5—C6—C7 | −178.6 (4) | C19—C21—C22—C17 | 52.1 (8) |
| C5—C6—C7—C2 | 0.1 (8) | C11—P1—C23—C28 | −99.4 (4) |
| C3—C2—C7—C6 | −1.2 (7) | C17—P1—C23—C28 | 146.1 (4) |
| N1—C2—C7—C6 | −176.5 (5) | Au—P1—C23—C28 | 26.1 (5) |
| C1—O1—C8—C9 | 76.9 (6) | C11—P1—C23—C24 | 30.7 (5) |
| C1—O1—C8—C10 | −162.0 (4) | C17—P1—C23—C24 | −83.8 (5) |
| C23—P1—C11—C12 | −175.4 (3) | Au—P1—C23—C24 | 156.2 (4) |
| C17—P1—C11—C12 | −61.6 (4) | C28—C23—C24—C25 | −56.0 (7) |
| Au—P1—C11—C12 | 60.1 (4) | P1—C23—C24—C25 | 172.5 (4) |
| C23—P1—C11—C16 | 63.3 (4) | C23—C24—C25—C26 | 55.8 (8) |
| C17—P1—C11—C16 | 177.1 (4) | C24—C25—C26—C27 | −51.6 (8) |
| Au—P1—C11—C16 | −61.2 (4) | C25—C26—C27—C28 | 49.3 (8) |
| C16—C11—C12—C13 | −56.7 (6) | C26—C27—C28—C23 | −51.7 (7) |
| P1—C11—C12—C13 | −179.5 (4) | C24—C23—C28—C27 | 54.6 (6) |
| C11—C12—C13—C14 | 55.2 (6) | P1—C23—C28—C27 | −171.8 (4) |
The National University of Singapore (grant No. R-143–000-213–112) is thanked for support.
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.
Brandenburg, K. (2006). DIAMOND. Crystal Impact GbR, Bonn, Germany.
Bruker (2000). SMART, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.
Farrugia, L. J. (1997). J. Appl. Cryst. 30, 565.
Hall, V. J., Siasios, G. & Tiekink, E. R. T. (1993). Aust. J. Chem. 46, 561–570.
Ho, S. Y., Cheng, E. C.-C., Tiekink, E. R. T. & Yam, V. W.-W. (2006). Inorg. Chem. 45, 8165–8174.
Ho, S. Y. & Tiekink, E. R. T. (2007). CrystEngComm, 9, 368–378.
Kuan, F. S., Ho, S. Y., Tadbuppa, P. P. & Tiekink, E. R. T. (2008). CrystEngComm, 10, 548–564.
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122.
Westrip, S. P. (2010). publCIF. In preparation.
Crystal engineering and luminescence imperatives motivated systematic studies of R3PAu[SC(OR')═NR''], for R, R' and R'' = alkyl and aryl, derivatives (Ho et al. 2006; Ho & Tiekink, 2007; Kuan et al., 2008). The synthesis and characterisation of the title compound, (I), was investigated in this context.
The gold atom in (I) exists within an SP donor set defined by the phosphine-P and thiolate-S atoms, Table 1 and Fig. 1. The carbonimidothioate ligand is functioning as a thiolate as seen by the magnitudes of the C1—S1 [1.750 (5) Å] and C1═N1 [1.257 (6) Å] bond distances. The coordination geometry is distorted from the ideal linear [S—Au—P = 172.45 (5) °] owing to the close approach of the O1 atom [3.134 (3) Å]. No specific intermolecular interactions are noted in the crystal packing.