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Supporting information
![]() | Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536810018179/hb5453sup1.cif |
![]() | Structure factor file (CIF format) https://doi.org/10.1107/S1600536810018179/hb5453Isup2.hkl |
CCDC reference: 781233
Key indicators
- Single-crystal X-ray study
- T = 223 K
- Mean
(C-C) = 0.007 Å
- Disorder in solvent or counterion
- R factor = 0.032
- wR factor = 0.092
- Data-to-parameter ratio = 20.3
checkCIF/PLATON results
No syntax errors found
Alert level B PLAT919_ALERT_3_B Reflection(s) # Likely Affected by the Beamstop 1
Alert level C PLAT202_ALERT_3_C Isotropic non-H Atoms in Anion/Solvent ......... 2 PLAT911_ALERT_3_C Missing # FCF Refl Between THmin & STh/L= 0.600 3 PLAT971_ALERT_2_C Large Calcd. Non-Metal Positive Residual Density 1.68 eA-3 PLAT972_ALERT_2_C Large Calcd. Non-Metal Negative Residual Density -1.74 eA-3 PLAT973_ALERT_2_C Large Calcd. Positive Residual Density on Au 1.05 eA-3 PLAT041_ALERT_1_C Calc. and Reported SumFormula Strings Differ ? PLAT042_ALERT_1_C Calc. and Reported MoietyFormula Strings Differ ? PLAT045_ALERT_1_C Calculated and Reported Z Differ by ............ 0.50 Ratio PLAT244_ALERT_4_C Low 'Solvent' Ueq as Compared to Neighbors of C28
Alert level G PLAT083_ALERT_2_G SHELXL Second Parameter in WGHT Unusually Large. 9.30 PLAT431_ALERT_2_G Short Inter HL..A Contact Cl1 .. Cl3 .. 3.17 Ang. PLAT302_ALERT_4_G Note: Anion/Solvent Disorder ................... 25.00 Perc. PLAT710_ALERT_4_G Delete 1-2-3 or 2-3-4 Linear Torsion Angle ... # 1 P1 -AU -S1 -C1 -143.50 1.20 1.555 1.555 1.555 1.555 PLAT710_ALERT_4_G Delete 1-2-3 or 2-3-4 Linear Torsion Angle ... # 2 S1 -AU -P1 -C22 171.40 1.20 1.555 1.555 1.555 1.555 PLAT710_ALERT_4_G Delete 1-2-3 or 2-3-4 Linear Torsion Angle ... # 3 S1 -AU -P1 -C16 53.80 1.20 1.555 1.555 1.555 1.555 PLAT710_ALERT_4_G Delete 1-2-3 or 2-3-4 Linear Torsion Angle ... # 4 S1 -AU -P1 -C10 -66.50 1.20 1.555 1.555 1.555 1.555
0 ALERT level A = In general: serious problem 1 ALERT level B = Potentially serious problem 9 ALERT level C = Check and explain 7 ALERT level G = General alerts; check 3 ALERT type 1 CIF construction/syntax error, inconsistent or missing data 5 ALERT type 2 Indicator that the structure model may be wrong or deficient 3 ALERT type 3 Indicator that the structure quality may be low 6 ALERT type 4 Improvement, methodology, query or suggestion 0 ALERT type 5 Informative message, check
Compound (I) was prepared following the standard literature procedure from the reaction of Ph3AuCl and EtOC(═S)N(H)(C6H4Cl-4) in the presence of NaOH (Hall et al., 1993). Yellow blocks of (I) 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 = 0.94–0.98 Å) and refined as riding with Uiso(H) = 1.2-1.5Ueq(C). The maximum and minimum residual electron density peaks of 1.73 and 1.87 e Å-3, respectively, were located 0.68 Å and 0.52 Å from the Cl2 atom. The solvent CH2Cl2 molecule (modelled isotropically) was disordered about a 2-fold axis of symmetry with the C and one Cl atom lying on the axis.
The structure of the title compound, (I), was investigated in the context of a study of molecules with the general formula R3PAu[SC(OR')═NR''], for R, R' and R'' = alkyl and aryl, of interest in terms of crystal engineering endeavours (Ho et al., 2006; Ho & Tiekink, 2007; Kuan et al., 2008).
The nearly linear SP coordination geometry observed for the Au atom in (I), Fig. 1, is defined by phosphine and thiolate ligands, Table 1. The small deviation from the ideal linearity [S—Au—P = 178.01 (4) °] is related to a short intramolecular Au···O contact [2.964 (4) Å].
The major feature of the crystal packing is the presence of C–H···N (leading to centrosymmetric dimers), C–H···S and C–H···π interactions that lead to the formation of supramolecular chains along the b axis, Fig. 2 and Table 2. Chains are arranged to form channels in which reside the (disordered) CH2Cl2 molecules, Fig. 3.
For the 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).
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).
[Au(C9H9ClNOS)(C18H15P)]·0.5CH2Cl2 | F(000) = 2792 |
Mr = 716.40 | Dx = 1.758 Mg m−3 |
Monoclinic, C2/c | Mo Kα radiation, λ = 0.71069 Å |
Hall symbol: -C 2yc | Cell parameters from 6681 reflections |
a = 30.5163 (16) Å | θ = 2.5–29.1° |
b = 8.5881 (5) Å | µ = 5.79 mm−1 |
c = 21.0518 (12) Å | T = 223 K |
β = 101.054 (1)° | Block, yellow |
V = 5414.8 (5) Å3 | 0.15 × 0.15 × 0.13 mm |
Z = 8 |
Bruker SMART CCD diffractometer | 6214 independent reflections |
Radiation source: fine-focus sealed tube | 5381 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.031 |
ω scans | θmax = 27.5°, θmin = 1.4° |
Absorption correction: multi-scan (SADABS; Bruker, 2000) | h = −39→38 |
Tmin = 0.672, Tmax = 1 | k = −6→11 |
18509 measured reflections | l = −27→27 |
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)] = 0.032 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.092 | H-atom parameters constrained |
S = 1.10 | w = 1/[σ2(Fo2) + (0.05P)2 + 9.3001P] where P = (Fo2 + 2Fc2)/3 |
6214 reflections | (Δ/σ)max = 0.001 |
306 parameters | Δρmax = 1.73 e Å−3 |
0 restraints | Δρmin = −1.87 e Å−3 |
[Au(C9H9ClNOS)(C18H15P)]·0.5CH2Cl2 | V = 5414.8 (5) Å3 |
Mr = 716.40 | Z = 8 |
Monoclinic, C2/c | Mo Kα radiation |
a = 30.5163 (16) Å | µ = 5.79 mm−1 |
b = 8.5881 (5) Å | T = 223 K |
c = 21.0518 (12) Å | 0.15 × 0.15 × 0.13 mm |
β = 101.054 (1)° |
Bruker SMART CCD diffractometer | 6214 independent reflections |
Absorption correction: multi-scan (SADABS; Bruker, 2000) | 5381 reflections with I > 2σ(I) |
Tmin = 0.672, Tmax = 1 | Rint = 0.031 |
18509 measured reflections |
R[F2 > 2σ(F2)] = 0.032 | 0 restraints |
wR(F2) = 0.092 | H-atom parameters constrained |
S = 1.10 | Δρmax = 1.73 e Å−3 |
6214 reflections | Δρmin = −1.87 e Å−3 |
306 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 | Occ. (<1) | |
Au | 0.082143 (5) | 0.03531 (2) | 0.391240 (8) | 0.02794 (7) | |
Cl1 | −0.15255 (7) | 0.6401 (2) | 0.23755 (9) | 0.0849 (7) | |
S1 | 0.01688 (4) | 0.16692 (14) | 0.35074 (6) | 0.0351 (3) | |
P1 | 0.14730 (3) | −0.08554 (13) | 0.43121 (5) | 0.0251 (2) | |
O1 | −0.00607 (11) | −0.0698 (4) | 0.41402 (17) | 0.0367 (8) | |
N1 | −0.06288 (12) | 0.1010 (5) | 0.38198 (19) | 0.0344 (9) | |
C1 | −0.02287 (15) | 0.0627 (5) | 0.3836 (2) | 0.0301 (9) | |
C2 | −0.08159 (14) | 0.2323 (6) | 0.3475 (2) | 0.0317 (9) | |
C3 | −0.08667 (17) | 0.2412 (7) | 0.2804 (2) | 0.0416 (11) | |
H3 | −0.0754 | 0.1612 | 0.2577 | 0.050* | |
C4 | −0.10818 (18) | 0.3672 (7) | 0.2469 (2) | 0.0460 (13) | |
H4 | −0.1114 | 0.3727 | 0.2017 | 0.055* | |
C5 | −0.1248 (2) | 0.4838 (7) | 0.2801 (3) | 0.0486 (14) | |
C6 | −0.1206 (2) | 0.4782 (7) | 0.3461 (3) | 0.0513 (15) | |
H6 | −0.1321 | 0.5586 | 0.3684 | 0.062* | |
C7 | −0.09900 (18) | 0.3514 (7) | 0.3793 (2) | 0.0436 (12) | |
H7 | −0.0962 | 0.3465 | 0.4245 | 0.052* | |
C8 | −0.03693 (17) | −0.1648 (6) | 0.4414 (3) | 0.0438 (12) | |
H8A | −0.0639 | −0.1860 | 0.4090 | 0.053* | |
H8B | −0.0456 | −0.1117 | 0.4783 | 0.053* | |
C9 | −0.0126 (2) | −0.3152 (7) | 0.4631 (3) | 0.0581 (16) | |
H9A | −0.0320 | −0.3831 | 0.4821 | 0.087* | |
H9B | 0.0141 | −0.2922 | 0.4951 | 0.087* | |
H9C | −0.0042 | −0.3663 | 0.4262 | 0.087* | |
C10 | 0.18807 (15) | −0.0764 (6) | 0.3788 (2) | 0.0291 (9) | |
C11 | 0.22367 (16) | −0.1789 (7) | 0.3848 (2) | 0.0387 (11) | |
H11 | 0.2262 | −0.2602 | 0.4152 | 0.046* | |
C12 | 0.25552 (17) | −0.1628 (8) | 0.3465 (3) | 0.0494 (14) | |
H12 | 0.2799 | −0.2317 | 0.3512 | 0.059* | |
C13 | 0.2511 (2) | −0.0445 (8) | 0.3014 (3) | 0.0568 (18) | |
H13 | 0.2727 | −0.0324 | 0.2755 | 0.068* | |
C14 | 0.2155 (2) | 0.0556 (8) | 0.2940 (3) | 0.0551 (16) | |
H14 | 0.2126 | 0.1346 | 0.2625 | 0.066* | |
C15 | 0.18380 (19) | 0.0406 (6) | 0.3324 (2) | 0.0408 (12) | |
H15 | 0.1594 | 0.1094 | 0.3273 | 0.049* | |
C16 | 0.17531 (15) | −0.0050 (5) | 0.5079 (2) | 0.0270 (9) | |
C17 | 0.21857 (16) | 0.0542 (6) | 0.5187 (2) | 0.0330 (10) | |
H17 | 0.2353 | 0.0500 | 0.4856 | 0.040* | |
C18 | 0.23708 (18) | 0.1196 (7) | 0.5781 (2) | 0.0459 (13) | |
H18 | 0.2662 | 0.1603 | 0.5851 | 0.055* | |
C19 | 0.2125 (2) | 0.1245 (6) | 0.6267 (2) | 0.0461 (13) | |
H19 | 0.2250 | 0.1692 | 0.6668 | 0.055* | |
C20 | 0.17016 (19) | 0.0650 (7) | 0.6171 (2) | 0.0426 (12) | |
H20 | 0.1539 | 0.0677 | 0.6507 | 0.051* | |
C21 | 0.15130 (17) | 0.0009 (6) | 0.5579 (2) | 0.0346 (10) | |
H21 | 0.1221 | −0.0390 | 0.5514 | 0.042* | |
C22 | 0.13970 (14) | −0.2882 (5) | 0.4482 (2) | 0.0276 (9) | |
C23 | 0.16943 (15) | −0.3689 (6) | 0.4943 (2) | 0.0349 (10) | |
H23 | 0.1946 | −0.3173 | 0.5178 | 0.042* | |
C24 | 0.16261 (19) | −0.5276 (6) | 0.5068 (3) | 0.0406 (12) | |
H24 | 0.1832 | −0.5823 | 0.5377 | 0.049* | |
C25 | 0.12537 (18) | −0.6007 (6) | 0.4730 (3) | 0.0430 (12) | |
H25 | 0.1206 | −0.7065 | 0.4809 | 0.052* | |
C26 | 0.0947 (2) | −0.5208 (7) | 0.4275 (3) | 0.0487 (14) | |
H26 | 0.0692 | −0.5721 | 0.4050 | 0.058* | |
C27 | 0.10177 (16) | −0.3649 (6) | 0.4152 (2) | 0.0360 (10) | |
H27 | 0.0809 | −0.3107 | 0.3845 | 0.043* | |
Cl2 | 0.5000 | 0.0930 (15) | 0.2500 | 0.288 (5)* | |
Cl3 | 0.44248 (15) | 0.3008 (6) | 0.2579 (2) | 0.0923 (12)* | 0.50 |
C28 | 0.5000 | 0.2911 (17) | 0.2500 | 0.101 (4)* | |
H28A | 0.5054 | 0.3360 | 0.2094 | 0.122* | 0.50 |
H28B | 0.5205 | 0.3360 | 0.2870 | 0.122* | 0.50 |
U11 | U22 | U33 | U12 | U13 | U23 | |
Au | 0.02219 (10) | 0.02619 (11) | 0.03374 (10) | 0.00001 (6) | 0.00111 (7) | 0.00359 (7) |
Cl1 | 0.0923 (13) | 0.0844 (13) | 0.0850 (12) | 0.0519 (11) | 0.0347 (10) | 0.0537 (11) |
S1 | 0.0244 (5) | 0.0319 (6) | 0.0480 (6) | 0.0006 (5) | 0.0041 (5) | 0.0140 (5) |
P1 | 0.0215 (5) | 0.0231 (5) | 0.0295 (5) | −0.0008 (4) | 0.0022 (4) | 0.0022 (4) |
O1 | 0.0297 (17) | 0.0335 (18) | 0.0484 (19) | 0.0048 (14) | 0.0108 (14) | 0.0135 (15) |
N1 | 0.0287 (19) | 0.037 (2) | 0.040 (2) | 0.0057 (17) | 0.0116 (16) | 0.0095 (18) |
C1 | 0.029 (2) | 0.031 (2) | 0.030 (2) | 0.0004 (18) | 0.0043 (17) | 0.0032 (18) |
C2 | 0.022 (2) | 0.037 (2) | 0.037 (2) | 0.0010 (19) | 0.0071 (17) | 0.011 (2) |
C3 | 0.044 (3) | 0.043 (3) | 0.037 (2) | 0.009 (2) | 0.007 (2) | 0.006 (2) |
C4 | 0.047 (3) | 0.055 (3) | 0.034 (2) | 0.003 (3) | 0.004 (2) | 0.010 (2) |
C5 | 0.040 (3) | 0.048 (3) | 0.059 (3) | 0.016 (2) | 0.013 (3) | 0.027 (3) |
C6 | 0.060 (4) | 0.043 (3) | 0.056 (3) | 0.020 (3) | 0.024 (3) | 0.008 (3) |
C7 | 0.050 (3) | 0.047 (3) | 0.038 (2) | 0.014 (3) | 0.018 (2) | 0.011 (2) |
C8 | 0.035 (3) | 0.041 (3) | 0.058 (3) | 0.003 (2) | 0.016 (2) | 0.021 (3) |
C9 | 0.053 (3) | 0.044 (3) | 0.082 (4) | 0.009 (3) | 0.026 (3) | 0.030 (3) |
C10 | 0.029 (2) | 0.032 (2) | 0.0255 (19) | −0.0056 (19) | 0.0037 (17) | −0.0043 (18) |
C11 | 0.035 (2) | 0.044 (3) | 0.036 (2) | 0.002 (2) | 0.0049 (19) | −0.004 (2) |
C12 | 0.032 (3) | 0.075 (4) | 0.043 (3) | −0.001 (3) | 0.010 (2) | −0.017 (3) |
C13 | 0.047 (3) | 0.088 (5) | 0.039 (3) | −0.023 (3) | 0.021 (3) | −0.021 (3) |
C14 | 0.069 (4) | 0.062 (4) | 0.037 (3) | −0.021 (3) | 0.017 (3) | 0.003 (3) |
C15 | 0.045 (3) | 0.040 (3) | 0.037 (2) | −0.007 (2) | 0.009 (2) | 0.004 (2) |
C16 | 0.026 (2) | 0.023 (2) | 0.031 (2) | 0.0017 (17) | 0.0029 (17) | 0.0024 (17) |
C17 | 0.026 (2) | 0.035 (3) | 0.037 (2) | −0.0047 (19) | 0.0043 (18) | 0.000 (2) |
C18 | 0.040 (3) | 0.047 (3) | 0.046 (3) | −0.013 (3) | −0.005 (2) | −0.003 (3) |
C19 | 0.064 (3) | 0.039 (3) | 0.032 (2) | −0.005 (3) | 0.000 (2) | 0.000 (2) |
C20 | 0.052 (3) | 0.044 (3) | 0.033 (2) | −0.002 (2) | 0.010 (2) | −0.002 (2) |
C21 | 0.031 (2) | 0.038 (3) | 0.036 (2) | −0.001 (2) | 0.0072 (19) | 0.001 (2) |
C22 | 0.028 (2) | 0.022 (2) | 0.034 (2) | −0.0022 (17) | 0.0084 (17) | 0.0012 (17) |
C23 | 0.028 (2) | 0.032 (3) | 0.043 (2) | −0.0005 (19) | 0.0030 (19) | 0.004 (2) |
C24 | 0.042 (3) | 0.031 (3) | 0.051 (3) | 0.011 (2) | 0.016 (2) | 0.010 (2) |
C25 | 0.056 (3) | 0.023 (2) | 0.055 (3) | −0.002 (2) | 0.023 (3) | 0.002 (2) |
C26 | 0.054 (4) | 0.035 (3) | 0.058 (3) | −0.015 (3) | 0.013 (3) | −0.009 (3) |
C27 | 0.037 (2) | 0.032 (3) | 0.037 (2) | −0.006 (2) | 0.001 (2) | 0.000 (2) |
Au—P1 | 2.2578 (11) | C12—H12 | 0.9400 |
Au—S1 | 2.3064 (11) | C13—C14 | 1.371 (10) |
Cl1—C5 | 1.740 (5) | C13—H13 | 0.9400 |
S1—C1 | 1.753 (5) | C14—C15 | 1.381 (8) |
P1—C22 | 1.801 (5) | C14—H14 | 0.9400 |
P1—C16 | 1.814 (5) | C15—H15 | 0.9400 |
P1—C10 | 1.816 (4) | C16—C17 | 1.392 (6) |
O1—C1 | 1.358 (5) | C16—C21 | 1.394 (6) |
O1—C8 | 1.447 (6) | C17—C18 | 1.387 (7) |
N1—C1 | 1.259 (6) | C17—H17 | 0.9400 |
N1—C2 | 1.402 (6) | C18—C19 | 1.380 (8) |
C2—C7 | 1.382 (7) | C18—H18 | 0.9400 |
C2—C3 | 1.393 (6) | C19—C20 | 1.368 (8) |
C3—C4 | 1.386 (7) | C19—H19 | 0.9400 |
C3—H3 | 0.9400 | C20—C21 | 1.382 (7) |
C4—C5 | 1.372 (8) | C20—H20 | 0.9400 |
C4—H4 | 0.9400 | C21—H21 | 0.9400 |
C5—C6 | 1.372 (9) | C22—C23 | 1.381 (6) |
C6—C7 | 1.390 (7) | C22—C27 | 1.396 (6) |
C6—H6 | 0.9400 | C23—C24 | 1.411 (7) |
C7—H7 | 0.9400 | C23—H23 | 0.9400 |
C8—C9 | 1.516 (7) | C24—C25 | 1.372 (8) |
C8—H8A | 0.9800 | C24—H24 | 0.9400 |
C8—H8B | 0.9800 | C25—C26 | 1.386 (9) |
C9—H9A | 0.9700 | C25—H25 | 0.9400 |
C9—H9B | 0.9700 | C26—C27 | 1.388 (8) |
C9—H9C | 0.9700 | C26—H26 | 0.9400 |
C10—C11 | 1.385 (7) | C27—H27 | 0.9400 |
C10—C15 | 1.389 (7) | Cl2—C28 | 1.701 (18) |
C11—C12 | 1.383 (7) | Cl3—C28 | 1.797 (5) |
C11—H11 | 0.9400 | C28—H28A | 0.9800 |
C12—C13 | 1.379 (9) | C28—H28B | 0.9800 |
P1—Au—S1 | 178.01 (4) | C14—C13—C12 | 120.8 (5) |
C1—S1—Au | 102.58 (16) | C14—C13—H13 | 119.6 |
C22—P1—C16 | 104.4 (2) | C12—C13—H13 | 119.6 |
C22—P1—C10 | 107.0 (2) | C13—C14—C15 | 120.2 (6) |
C16—P1—C10 | 105.3 (2) | C13—C14—H14 | 119.9 |
C22—P1—Au | 112.37 (14) | C15—C14—H14 | 119.9 |
C16—P1—Au | 112.79 (15) | C14—C15—C10 | 119.8 (5) |
C10—P1—Au | 114.24 (15) | C14—C15—H15 | 120.1 |
C1—O1—C8 | 116.4 (4) | C10—C15—H15 | 120.1 |
C1—N1—C2 | 121.4 (4) | C17—C16—C21 | 118.9 (4) |
N1—C1—O1 | 120.5 (4) | C17—C16—P1 | 123.7 (4) |
N1—C1—S1 | 126.7 (4) | C21—C16—P1 | 117.4 (3) |
O1—C1—S1 | 112.8 (3) | C18—C17—C16 | 120.3 (5) |
C7—C2—C3 | 118.1 (4) | C18—C17—H17 | 119.9 |
C7—C2—N1 | 120.1 (4) | C16—C17—H17 | 119.9 |
C3—C2—N1 | 121.6 (5) | C19—C18—C17 | 119.7 (5) |
C4—C3—C2 | 120.6 (5) | C19—C18—H18 | 120.2 |
C4—C3—H3 | 119.7 | C17—C18—H18 | 120.2 |
C2—C3—H3 | 119.7 | C20—C19—C18 | 120.7 (5) |
C5—C4—C3 | 119.8 (5) | C20—C19—H19 | 119.6 |
C5—C4—H4 | 120.1 | C18—C19—H19 | 119.6 |
C3—C4—H4 | 120.1 | C19—C20—C21 | 120.0 (5) |
C6—C5—C4 | 121.2 (5) | C19—C20—H20 | 120.0 |
C6—C5—Cl1 | 119.3 (5) | C21—C20—H20 | 120.0 |
C4—C5—Cl1 | 119.5 (5) | C20—C21—C16 | 120.4 (5) |
C5—C6—C7 | 118.6 (5) | C20—C21—H21 | 119.8 |
C5—C6—H6 | 120.7 | C16—C21—H21 | 119.8 |
C7—C6—H6 | 120.7 | C23—C22—C27 | 118.9 (4) |
C2—C7—C6 | 121.8 (5) | C23—C22—P1 | 122.2 (3) |
C2—C7—H7 | 119.1 | C27—C22—P1 | 118.9 (3) |
C6—C7—H7 | 119.1 | C22—C23—C24 | 121.0 (4) |
O1—C8—C9 | 106.3 (4) | C22—C23—H23 | 119.5 |
O1—C8—H8A | 110.5 | C24—C23—H23 | 119.5 |
C9—C8—H8A | 110.5 | C25—C24—C23 | 118.9 (5) |
O1—C8—H8B | 110.5 | C25—C24—H24 | 120.5 |
C9—C8—H8B | 110.5 | C23—C24—H24 | 120.5 |
H8A—C8—H8B | 108.7 | C24—C25—C26 | 120.9 (5) |
C8—C9—H9A | 109.5 | C24—C25—H25 | 119.5 |
C8—C9—H9B | 109.5 | C26—C25—H25 | 119.5 |
H9A—C9—H9B | 109.5 | C25—C26—C27 | 119.9 (5) |
C8—C9—H9C | 109.5 | C25—C26—H26 | 120.1 |
H9A—C9—H9C | 109.5 | C27—C26—H26 | 120.1 |
H9B—C9—H9C | 109.5 | C26—C27—C22 | 120.4 (5) |
C11—C10—C15 | 119.4 (4) | C26—C27—H27 | 119.8 |
C11—C10—P1 | 122.2 (4) | C22—C27—H27 | 119.8 |
C15—C10—P1 | 118.4 (4) | Cl2—C28—Cl3 | 92.7 (5) |
C12—C11—C10 | 120.6 (5) | Cl2—C28—H28A | 113.2 |
C12—C11—H11 | 119.7 | Cl3—C28—H28A | 113.2 |
C10—C11—H11 | 119.7 | Cl2—C28—H28B | 113.2 |
C11—C12—C13 | 119.2 (6) | Cl3—C28—H28B | 113.2 |
C11—C12—H12 | 120.4 | H28A—C28—H28B | 110.5 |
C13—C12—H12 | 120.4 | ||
P1—Au—S1—C1 | −143.5 (12) | C12—C13—C14—C15 | 1.0 (9) |
S1—Au—P1—C22 | 171.4 (12) | C13—C14—C15—C10 | −0.1 (9) |
S1—Au—P1—C16 | 53.8 (12) | C11—C10—C15—C14 | −1.4 (8) |
S1—Au—P1—C10 | −66.5 (12) | P1—C10—C15—C14 | 176.8 (4) |
C2—N1—C1—O1 | −176.1 (4) | C22—P1—C16—C17 | 114.7 (4) |
C2—N1—C1—S1 | 5.2 (7) | C10—P1—C16—C17 | 2.2 (5) |
C8—O1—C1—N1 | 2.4 (7) | Au—P1—C16—C17 | −123.0 (4) |
C8—O1—C1—S1 | −178.8 (4) | C22—P1—C16—C21 | −67.0 (4) |
Au—S1—C1—N1 | 170.6 (4) | C10—P1—C16—C21 | −179.5 (4) |
Au—S1—C1—O1 | −8.2 (4) | Au—P1—C16—C21 | 55.3 (4) |
C1—N1—C2—C7 | −121.0 (5) | C21—C16—C17—C18 | −0.8 (7) |
C1—N1—C2—C3 | 64.5 (7) | P1—C16—C17—C18 | 177.5 (4) |
C7—C2—C3—C4 | 0.7 (8) | C16—C17—C18—C19 | 0.5 (8) |
N1—C2—C3—C4 | 175.3 (5) | C17—C18—C19—C20 | 0.3 (9) |
C2—C3—C4—C5 | −0.3 (8) | C18—C19—C20—C21 | −0.9 (9) |
C3—C4—C5—C6 | −0.1 (9) | C19—C20—C21—C16 | 0.6 (8) |
C3—C4—C5—Cl1 | −179.0 (5) | C17—C16—C21—C20 | 0.2 (7) |
C4—C5—C6—C7 | 0.1 (10) | P1—C16—C21—C20 | −178.1 (4) |
Cl1—C5—C6—C7 | 178.9 (5) | C16—P1—C22—C23 | −31.3 (4) |
C3—C2—C7—C6 | −0.7 (8) | C10—P1—C22—C23 | 80.0 (4) |
N1—C2—C7—C6 | −175.4 (5) | Au—P1—C22—C23 | −153.9 (3) |
C5—C6—C7—C2 | 0.4 (9) | C16—P1—C22—C27 | 146.6 (4) |
C1—O1—C8—C9 | 171.6 (5) | C10—P1—C22—C27 | −102.1 (4) |
C22—P1—C10—C11 | −35.4 (4) | Au—P1—C22—C27 | 24.0 (4) |
C16—P1—C10—C11 | 75.3 (4) | C27—C22—C23—C24 | 1.9 (7) |
Au—P1—C10—C11 | −160.4 (3) | P1—C22—C23—C24 | 179.9 (4) |
C22—P1—C10—C15 | 146.5 (4) | C22—C23—C24—C25 | −1.1 (7) |
C16—P1—C10—C15 | −102.9 (4) | C23—C24—C25—C26 | −0.2 (8) |
Au—P1—C10—C15 | 21.4 (4) | C24—C25—C26—C27 | 0.6 (9) |
C15—C10—C11—C12 | 1.9 (7) | C25—C26—C27—C22 | 0.3 (8) |
P1—C10—C11—C12 | −176.2 (4) | C23—C22—C27—C26 | −1.5 (7) |
C10—C11—C12—C13 | −1.0 (8) | P1—C22—C27—C26 | −179.5 (4) |
C11—C12—C13—C14 | −0.5 (9) |
Cg1 is the centroid of the C22–C27 ring. |
D—H···A | D—H | H···A | D···A | D—H···A |
C21—H21···N1i | 0.94 | 2.55 | 3.310 (6) | 138 |
C26—H26···S1ii | 0.94 | 2.86 | 3.738 (6) | 156 |
C7—H7···Cg1i | 0.94 | 2.96 | 3.784 (5) | 147 |
Symmetry codes: (i) −x, −y, −z+1; (ii) x, y−1, z. |
Experimental details
Crystal data | |
Chemical formula | [Au(C9H9ClNOS)(C18H15P)]·0.5CH2Cl2 |
Mr | 716.40 |
Crystal system, space group | Monoclinic, C2/c |
Temperature (K) | 223 |
a, b, c (Å) | 30.5163 (16), 8.5881 (5), 21.0518 (12) |
β (°) | 101.054 (1) |
V (Å3) | 5414.8 (5) |
Z | 8 |
Radiation type | Mo Kα |
µ (mm−1) | 5.79 |
Crystal size (mm) | 0.15 × 0.15 × 0.13 |
Data collection | |
Diffractometer | Bruker SMART CCD |
Absorption correction | Multi-scan (SADABS; Bruker, 2000) |
Tmin, Tmax | 0.672, 1 |
No. of measured, independent and observed [I > 2σ(I)] reflections | 18509, 6214, 5381 |
Rint | 0.031 |
(sin θ/λ)max (Å−1) | 0.650 |
Refinement | |
R[F2 > 2σ(F2)], wR(F2), S | 0.032, 0.092, 1.10 |
No. of reflections | 6214 |
No. of parameters | 306 |
H-atom treatment | H-atom parameters constrained |
Δρmax, Δρmin (e Å−3) | 1.73, −1.87 |
Computer programs: SMART (Bruker, 2000), SAINT (Bruker, 2000), PATTY in DIRDIF92 (Beurskens et al., 1992), SHELXL97 (Sheldrick, 2008), ORTEP-3 (Farrugia, 1997) and DIAMOND (Brandenburg, 2006), publCIF (Westrip, 2010).
Cg1 is the centroid of the C22–C27 ring. |
D—H···A | D—H | H···A | D···A | D—H···A |
C21—H21···N1i | 0.94 | 2.55 | 3.310 (6) | 138 |
C26—H26···S1ii | 0.94 | 2.86 | 3.738 (6) | 156 |
C7—H7···Cg1i | 0.94 | 2.96 | 3.784 (5) | 147 |
Symmetry codes: (i) −x, −y, −z+1; (ii) x, y−1, z. |
The structure of the title compound, (I), was investigated in the context of a study of molecules with the general formula R3PAu[SC(OR')═NR''], for R, R' and R'' = alkyl and aryl, of interest in terms of crystal engineering endeavours (Ho et al., 2006; Ho & Tiekink, 2007; Kuan et al., 2008).
The nearly linear SP coordination geometry observed for the Au atom in (I), Fig. 1, is defined by phosphine and thiolate ligands, Table 1. The small deviation from the ideal linearity [S—Au—P = 178.01 (4) °] is related to a short intramolecular Au···O contact [2.964 (4) Å].
The major feature of the crystal packing is the presence of C–H···N (leading to centrosymmetric dimers), C–H···S and C–H···π interactions that lead to the formation of supramolecular chains along the b axis, Fig. 2 and Table 2. Chains are arranged to form channels in which reside the (disordered) CH2Cl2 molecules, Fig. 3.