4
A. A. S. ELKHALDY ET AL.
aluminum slides coated with silica gel 60, using appropriate 12. 63. Found: %H, 3.65; %C 25.38; %S, 11.60; %P, 5.85;
solvent systems; spots were visualized under ultra-violet
light. On re-dissolving the O, O’-1,1,2,2-tetramethylethylene
dithiophosphatogold (III)dichloride in benzene and adding a
few drops of n-hexane, a yellow crystalline solid (suitable for
X-ray diffraction) was obtained,
%Au, 35.788; %Cl, 12.76.
Complex 7, [(C5H9O)2PS2] AuCl2: Product is 79% yield
and brown oily liquid. IR ꢀ (P)–O–C, 997s; ꢀ P–O–(C),
1
917 m; ꢀ P ¼ S 645 m; ꢀ P–S 548 w; ꢀ (Au–S) 446 w, H
NMR (CDCl3): 1.5–2.4 (m, 16H, CH2); 4.96–5.30 (m, 2H,
CHO). 13C NMR (CDCl3): 73.5(s, OCH) 32.3s 23,1 (s,
CH2). 31P NMR (CDCl3): d 102.5. Anal. Calcd. for
C10H18AuCl2O2PS2: %H, 3.40; %C, 22.52; %S, 12.02; %P,
5.80; %Au, 36.93; %Cl, 13.29. Found: %H, 3.29; %C 22.18;
%S, 12.70; %P, 5.38; %Au, 36.62; %Cl, 13.59.
[(nPrO)2PS2] AuCl2: product is 84% yield and oily brow
complex IR ꢀ (P)–O–C,1010s; ꢀ P–O–(C), 913 m; ꢀ P ¼ S
1
646 m; ꢀ P–S 525w; ꢀ (Au–S) 479w, H NMR (CDCl3): 1.10
(t, J ¼ 5.8Hz, 6H, 2xCH3), 1.84 (m, 4H, 2xCH2); 4.27
(J ¼ 5.3 Hz, 4H, 2xCH2). 13C NMR(CDCl3): 10.14 (s,CH3),
70.04(s, OCH2), 23.18 (s,CH2), 31P NMR (CDCl3): d 88.9.
Anal. Calcd for C6H14O2PS2AuCl2: %H, 2.93; %C 14.97; %S,
13.32; %P, 6.43; %Au, 40.93; %Cl, 14. 49. Found: %H, 2.74;
%C 14.90; %S, 13.90; %P, 5.86; %Au, 41.19; %Cl, 14.73
Complex 1, [(EtO)2PS2] AuCl2: Product is 86% yield and
brown oily liquid. IR ꢀ (P)–O–C,1022s; ꢀ P–O–(C), 958 m;
ꢀ P ¼ S, 617 m; ꢀ P–S, 581w; ꢀ (Au–S) 426w, 1H NMR
(CDCl3): 1.40 (t, J ¼ 6 Hz, 6H, 2xCH3; 4.35 (q, J ¼ 6 Hz, 4H,
2xCH2). 13C NMR(CDCl3): 15.91 (s, CH3), 64.13 (s, OCH2).
Complex 8, [OCMe2CMe2OPS2]AuCl2: Product is 80%
yield and yellow solid. M.P.1810C. IR ꢀ (P)–O–C,920 s; ꢀ
P–O–(C), 874 m; Ring vibration 924s; P ¼ S 645 m; ꢀ P–S
536 w; ꢀ (Au–S) 439w. 1H NMR (CDCl3): 1.60 (s, 12 H,
4xCH3). 13C NMR (CDCl3): 24.41 (s, CH3) 91.22 (s, OC);
31P NMR (CDCl3):
d
102.4. Anal. Calcd. for
C6H12AuCl2O2PS2: %H, 2.52; %C, 15.04; %S, 13.38; %P,
6.46; %Au, 41.10; %Cl, 14.79. Found: %H, 2.42; %C 15.23;
%S, 13.20; %P, 6.84; %Au, 41.66; %Cl, 14.49.
31P NMR (CDCl3):
d
89.8. Anal. Calcd for
C4H10O2PS2AuCl2: %H, 2.22; %C 10.60; %S, 14.15; %P, 6.83;
%Au, 43.47; %Cl, 15. 64. Found: %H, 2.10; %C 10.45; %S,
14.90; %P, 6.42; %Au, 43.89; %Cl, 14.57.
X-ray diffraction analysis
Single, yellow, needle-shaped crystals of [S2POCMe2CMe2O]
AuCl2 were used as received.
Complex 3, [(j-PrO)2PS2] AuCl2: Product is 88% yield
and brown oily liquid. IR ꢀ (P)–O–C, 1022s; ꢀ P–O–(C),
A
suitable crystal
(0.26 ꢁ 0.13 ꢁ 0.05 mm3) was selected and mounted on a
nylon loop with paratone oil on a Bruker APEX-II CCD
diffractometer.The crystal was kept at T ¼ 173 (2) K during
data collection.[35] The structure was solved with the Olex2
structure solution program[36], using the Charge Flipping
solution method. The model was refined with version 2014/
6 of XL,[37] using Least Squares minimization.
1
901s; ꢀ P ¼ S 685m; ꢀ P–S 525w; ꢀ (Au–S) 405w, H NMR
(CDCl3): 1.52 (d, J ¼ 5.5Hz, 6H, 2xCH3); 4.90 (m, 1H, CH).
13C NMR (CDCl3): 23.19 (s, CH3), 72.4 (s, OCH). 31P
NMR (CDCl3): d 87.6. Anal. Calcd for C6H14O2PS2AuCl2:
%H, 2.93; %C 14.97; %S, 13.32; %P, 6.43; %Au, 40.93; %Cl,
14. 73. Found: %H, 2.79; %C 14.71; %S, 13.90; %P, 6.85;
%Au, 41.45; %Cl, 14.63.
Crystal Data: C18H36Au3Cl6O6P3S6, Mr ¼1437.34, triclinic,
P-1 (No. 2), a ¼ 10.2474(12) Å, b ¼ 11.2734(13) Å, c ¼
17.483(2) Å, a ¼ 96.9900(10)ꢂ, b ¼ 94.0090(10)ꢂ, c ¼
91.9340(10)ꢂ, V ¼ 1998.0(4) Å3, T ¼ 173(2) K, Z ¼ 2, Z’ ¼ 1, l
(MoKa) ¼ 11.853, 33154 reflections measured, 7329 unique
(Rint ¼ 0.0513) which were used in all calculations. The final
wR2 was 0.0947 (all data) and R1 was 0.0364 (I > 2(I))
(Table 1).
Complex 4, [(j-BuO)2PS2] AuCl2: Product is 85% yield
and yellow oily liquid. IR ꢀ (P)–O–C, 1020s; ꢀ P–O–(C),
1
993m; ꢀ P ¼ S 657m; ꢀ P–S 568m; ꢀ (Au–S) 477w. H NMR
(CDCl3): 0.98 (d, J ¼ 3.6Hz, 6H, 2xCH3); 2.0 (m, 1H, CH);
4.05 (d, J ¼ 6.4Hz, 2H, CH2). 13C NMR(CDCl3): 19.20 (s,
CH3), 70.92 (s, OCH2). 29.25(s, CH). 31P NMR (CDCl3): d
88.9. Anal. Calcd. for C8H18O2PS2AuCl2: %H, 3.56; %C,
18.86; %S, 12.59; %P, 6.08; %Au, 38.68; %Cl, 13.92. Found:
%H, 3.78; %C 18.65; %S, 12.70; %P, 6.53; %Au, 38.46;
%Cl, 13.67.
Experimental Extended. Data were collected using a
Bruker APEX-II CCD diffractometer equipped with an
Oxford Cryosystems low-temperature apparatus operating at
T ¼ 173 (2) K.
Complex 5, [(PhO)2PS2]AuCl2: Product is 82% yield and
yellow oily liquid. IR ꢀ (P)–O–C, 1010s; ꢀ P–O–(C), 913s; ꢀ
P ¼ S 646m; ꢀ P–S 525w; ꢀ (Au–S) 479w, 1H NMR
(CDCl3): 7.26 (m, ArH). 13C NMR (CDCl3): 121.47, 129.34,
123.57(s, CH), 150.35(s. OC). 31P NMR (CDCl3): d 91.3.
Anal. Calcd. for C6H14O2PS2AuCl2: %H, 1.83; %C 26.24;
%S, 11.67; %P, 5.64; %Au, 35.86; %Cl, 12.91. Found: %H,
1.75; %C 26.03; %S, 11.60; %P, 5.77; %Au, 35.64; %Cl, 12.51.
Complex 6, [(C6H11O)2PS2]AuCl2: Product is 83% yield,
yellow oily liquid. IR ꢀ (P)–O–C, 1120s; ꢀ P–O–(C), 965 m;
ꢀ P ¼ S 680 m; ꢀ P–S 578w; ꢀ (Au–S) 481w, 1H NMR
(CDCl3): 1.50–2.0 (m, 20H, CH2); 3.85 (m, 2H, CHO). 13C
NMR(CDCl3): 78.6 (s, CH) 31.23, 23,14, 25.12 (s, CH2). 31P
NMR (CDCl3): d 102.2 Anal. Calcd. for C12H22AuCl2O2PS2:
Data were measured using / and x scans of ꢀ0.50ꢂ per
frame for 20.10 s using MoKa radiation (sealed tube, 50 kV,
40mA). The total number of runs and images was based on the
strategy calculation from the program COSMO (BRUKER,
V1.61, 2009). The actually achieve resolution was H ¼ 25.377.
Cell parameters were retrieved using the SAINT (Bruker,
V8.27A, 2012) software and refined using SAINT (Bruker,
V8.27A, 2012) on 9836 reflections. Data reduction was per-
formed using the SAINT (Bruker, V8.27A, 2012) software
which corrects for Lorentz polarization. The final complete-
ness is 93.20 out to 25.377 in H. The absorption coefficient
(MU) of this material is 11.853 and the minimum and max-
%H, 3.95; %C; 25.67%S, 11.42; %P, 5.51; %Au, 35.09; %Cl, imum transmissions are 0.4840 and 0.7452.