Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536802020512/cf6221sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S1600536802020512/cf6221Isup2.hkl |
CCDC reference: 202288
To a solution of bis(2-mercaptoimidazolyl)borate, Na[BmMe], in dichloromethane (10 ml) was added Ph3PAuNO3 (1:1 stoichiometric ratio), dissolved in dichloromethane (10 ml). The resulting mixture was stirred for 3 h and filtered to remove NaNO3. The solution was evaporated to 5 ml and ether was added to give an off-white precipitate. Block crystals were obtained by slow diffusion of ether into a dichloromethane solution of the title compound.
The maximum and minimum residual electron-density peaks in the final difference Fourier map were located at distances of 0.89 and 0.88 Å, respectively, from Au1.
Data collection: SMART (Bruker, 2001); cell refinement: SAINT (Bruker, 1999); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 1990); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: SHELXTL (Siemens, 1996); software used to prepare material for publication: SHELXL97.
Fig. 1. The molecular structure of (I). Displacement ellipsoids are shown at the 50% probability level for non-H atoms. |
[Au(C8H12N4S2)(C18H15P)] | Dx = 1.700 Mg m−3 |
Mr = 698.38 | Melting point: not measured K |
Monoclinic, P21/c | Mo Kα radiation, λ = 0.71073 Å |
a = 20.7037 (12) Å | Cell parameters from 8187 reflections |
b = 8.6870 (5) Å | θ = 2.0–28.3° |
c = 15.2487 (9) Å | µ = 5.62 mm−1 |
β = 95.643 (1)° | T = 110 K |
V = 2729.2 (3) Å3 | Block, colorless |
Z = 4 | 0.29 × 0.13 × 0.13 mm |
F(000) = 1368 |
Bruker SMART area-detector diffractometer | 6619 independent reflections |
Radiation source: fine-focus sealed tube | 5410 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.087 |
ω scans | θmax = 28.3°, θmin = 2.0° |
Absorption correction: multi-scan (SADABS; Blessing, 1995) | h = −26→26 |
Tmin = 0.351, Tmax = 0.495 | k = −11→11 |
17546 measured reflections | l = −20→20 |
Refinement on F2 | Secondary atom site location: difference Fourier map |
Least-squares matrix: full | Hydrogen site location: inferred from neighbouring sites |
R[F2 > 2σ(F2)] = 0.041 | H-atom parameters constrained |
wR(F2) = 0.110 | w = 1/[σ2(Fo2) + (0.0604P)2] where P = (Fo2 + 2Fc2)/3 |
S = 1.04 | (Δ/σ)max = 0.001 |
6619 reflections | Δρmax = 1.86 e Å−3 |
319 parameters | Δρmin = −2.35 e Å−3 |
0 restraints | Extinction correction: SHELXL97, Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4 |
Primary atom site location: structure-invariant direct methods | Extinction coefficient: 0.00132 (17) |
[Au(C8H12N4S2)(C18H15P)] | V = 2729.2 (3) Å3 |
Mr = 698.38 | Z = 4 |
Monoclinic, P21/c | Mo Kα radiation |
a = 20.7037 (12) Å | µ = 5.62 mm−1 |
b = 8.6870 (5) Å | T = 110 K |
c = 15.2487 (9) Å | 0.29 × 0.13 × 0.13 mm |
β = 95.643 (1)° |
Bruker SMART area-detector diffractometer | 6619 independent reflections |
Absorption correction: multi-scan (SADABS; Blessing, 1995) | 5410 reflections with I > 2σ(I) |
Tmin = 0.351, Tmax = 0.495 | Rint = 0.087 |
17546 measured reflections |
R[F2 > 2σ(F2)] = 0.041 | 0 restraints |
wR(F2) = 0.110 | H-atom parameters constrained |
S = 1.04 | Δρmax = 1.86 e Å−3 |
6619 reflections | Δρmin = −2.35 e Å−3 |
319 parameters |
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 | 0.244832 (9) | 0.42959 (2) | 0.041577 (11) | 0.03475 (9) | |
S1 | 0.14261 (6) | 0.22195 (14) | 0.05990 (8) | 0.0352 (3) | |
S2 | 0.18706 (6) | 0.65295 (15) | −0.00472 (8) | 0.0399 (3) | |
P1 | 0.32909 (6) | 0.26726 (13) | 0.07210 (7) | 0.0290 (2) | |
N1 | 0.13956 (19) | 0.3516 (4) | 0.2243 (2) | 0.0310 (8) | |
N2 | 0.1289 (2) | 0.1015 (5) | 0.2217 (3) | 0.0385 (9) | |
N3 | 0.1065 (2) | 0.5835 (4) | 0.1259 (3) | 0.0301 (8) | |
N4 | 0.0593 (2) | 0.6941 (5) | 0.0079 (3) | 0.0366 (9) | |
C1 | 0.1368 (2) | 0.2273 (5) | 0.1707 (3) | 0.0306 (9) | |
C2 | 0.1326 (3) | 0.3013 (6) | 0.3092 (3) | 0.0395 (11) | |
H2 | 0.1323 | 0.3635 | 0.3588 | 0.047* | |
C3 | 0.1264 (3) | 0.1472 (7) | 0.3074 (3) | 0.0449 (12) | |
H3 | 0.1214 | 0.0835 | 0.3553 | 0.054* | |
C4 | 0.1252 (4) | −0.0569 (6) | 0.1891 (5) | 0.0575 (17) | |
H4A | 0.0812 | −0.0803 | 0.1674 | 0.086* | |
H4B | 0.1393 | −0.1261 | 0.2362 | 0.086* | |
H4C | 0.1526 | −0.0682 | 0.1423 | 0.086* | |
C5 | 0.1164 (2) | 0.6391 (5) | 0.0460 (3) | 0.0323 (9) | |
C6 | 0.0416 (3) | 0.6022 (6) | 0.1368 (3) | 0.0376 (11) | |
H6 | 0.0216 | 0.5729 | 0.1862 | 0.045* | |
C7 | 0.0121 (3) | 0.6698 (6) | 0.0645 (4) | 0.0424 (12) | |
H7 | −0.0316 | 0.6953 | 0.0544 | 0.051* | |
C8 | 0.0488 (3) | 0.7720 (7) | −0.0770 (4) | 0.0526 (15) | |
H8A | 0.0718 | 0.8680 | −0.0742 | 0.079* | |
H8B | 0.0032 | 0.7910 | −0.0908 | 0.079* | |
H8C | 0.0643 | 0.7082 | −0.1219 | 0.079* | |
C11 | 0.4037 (2) | 0.3685 (6) | 0.1083 (3) | 0.0352 (10) | |
C12 | 0.4543 (3) | 0.3034 (7) | 0.1604 (4) | 0.0499 (13) | |
H12 | 0.4501 | 0.2038 | 0.1815 | 0.060* | |
C13 | 0.5118 (3) | 0.3839 (10) | 0.1822 (5) | 0.069 (2) | |
H13 | 0.5462 | 0.3381 | 0.2165 | 0.083* | |
C14 | 0.5170 (4) | 0.5322 (11) | 0.1522 (6) | 0.078 (2) | |
H14 | 0.5554 | 0.5862 | 0.1659 | 0.094* | |
C15 | 0.4669 (4) | 0.6014 (9) | 0.1028 (6) | 0.081 (2) | |
H15 | 0.4709 | 0.7027 | 0.0844 | 0.097* | |
C16 | 0.4097 (3) | 0.5200 (7) | 0.0799 (5) | 0.0562 (15) | |
H16 | 0.3755 | 0.5668 | 0.0457 | 0.067* | |
C21 | 0.3171 (2) | 0.1268 (6) | 0.1576 (3) | 0.0314 (9) | |
C22 | 0.3188 (3) | −0.0301 (6) | 0.1440 (3) | 0.0469 (13) | |
H22 | 0.3291 | −0.0681 | 0.0901 | 0.056* | |
C23 | 0.3052 (4) | −0.1320 (7) | 0.2100 (4) | 0.0584 (17) | |
H23 | 0.3063 | −0.2376 | 0.2003 | 0.070* | |
C24 | 0.2899 (3) | −0.0750 (6) | 0.2909 (4) | 0.0500 (15) | |
H24 | 0.2807 | −0.1427 | 0.3353 | 0.060* | |
C25 | 0.2884 (3) | 0.0810 (6) | 0.3050 (3) | 0.0446 (13) | |
H25 | 0.2785 | 0.1190 | 0.3591 | 0.054* | |
C26 | 0.3015 (3) | 0.1816 (6) | 0.2387 (3) | 0.0405 (11) | |
H26 | 0.2999 | 0.2871 | 0.2485 | 0.049* | |
C31 | 0.3490 (2) | 0.1472 (5) | −0.0197 (3) | 0.0319 (9) | |
C32 | 0.4112 (3) | 0.1249 (7) | −0.0400 (4) | 0.0443 (12) | |
H32 | 0.4454 | 0.1740 | −0.0071 | 0.053* | |
C33 | 0.4238 (3) | 0.0294 (7) | −0.1096 (4) | 0.0551 (15) | |
H33 | 0.4662 | 0.0146 | −0.1232 | 0.066* | |
C34 | 0.3727 (4) | −0.0436 (7) | −0.1584 (4) | 0.0566 (16) | |
H34 | 0.3807 | −0.1055 | −0.2060 | 0.068* | |
C35 | 0.3109 (3) | −0.0251 (7) | −0.1371 (4) | 0.0525 (15) | |
H35 | 0.2770 | −0.0774 | −0.1687 | 0.063* | |
C36 | 0.2982 (3) | 0.0727 (5) | −0.0676 (3) | 0.0398 (11) | |
H36 | 0.2558 | 0.0872 | −0.0539 | 0.048* | |
B1 | 0.1563 (3) | 0.5210 (6) | 0.2008 (3) | 0.0327 (11) | |
H1A | 0.1555 | 0.5853 | 0.2526 | 0.039* | |
H1B | 0.1996 | 0.5250 | 0.1819 | 0.039* |
U11 | U22 | U33 | U12 | U13 | U23 | |
Au1 | 0.03801 (13) | 0.03725 (13) | 0.02962 (12) | 0.00994 (7) | 0.00644 (7) | 0.00254 (7) |
S1 | 0.0398 (6) | 0.0350 (6) | 0.0300 (5) | −0.0011 (5) | 0.0002 (5) | −0.0043 (5) |
S2 | 0.0447 (7) | 0.0349 (6) | 0.0421 (7) | 0.0090 (5) | 0.0135 (5) | 0.0116 (5) |
P1 | 0.0316 (6) | 0.0286 (6) | 0.0272 (5) | 0.0012 (5) | 0.0054 (4) | −0.0005 (4) |
N1 | 0.041 (2) | 0.0271 (19) | 0.0248 (18) | 0.0021 (17) | 0.0027 (15) | 0.0035 (14) |
N2 | 0.041 (2) | 0.029 (2) | 0.045 (2) | −0.0023 (17) | 0.0044 (19) | 0.0065 (17) |
N3 | 0.038 (2) | 0.0226 (18) | 0.0304 (19) | 0.0040 (15) | 0.0048 (16) | 0.0015 (14) |
N4 | 0.041 (2) | 0.031 (2) | 0.036 (2) | 0.0046 (17) | −0.0012 (17) | 0.0035 (16) |
C1 | 0.028 (2) | 0.030 (2) | 0.034 (2) | 0.0001 (18) | 0.0006 (17) | 0.0018 (18) |
C2 | 0.050 (3) | 0.043 (3) | 0.027 (2) | 0.002 (2) | 0.009 (2) | 0.002 (2) |
C3 | 0.057 (3) | 0.042 (3) | 0.037 (3) | −0.004 (3) | 0.011 (2) | 0.014 (2) |
C4 | 0.069 (4) | 0.027 (3) | 0.076 (4) | −0.004 (3) | 0.002 (4) | 0.002 (3) |
C5 | 0.042 (3) | 0.022 (2) | 0.033 (2) | 0.0066 (19) | 0.0049 (19) | −0.0018 (17) |
C6 | 0.041 (3) | 0.035 (3) | 0.038 (3) | 0.002 (2) | 0.009 (2) | 0.001 (2) |
C7 | 0.033 (3) | 0.046 (3) | 0.048 (3) | 0.001 (2) | 0.005 (2) | 0.003 (2) |
C8 | 0.050 (3) | 0.062 (4) | 0.044 (3) | 0.009 (3) | −0.003 (2) | 0.018 (3) |
C11 | 0.032 (2) | 0.038 (3) | 0.037 (2) | −0.002 (2) | 0.0055 (19) | −0.010 (2) |
C12 | 0.042 (3) | 0.054 (3) | 0.053 (3) | 0.002 (3) | 0.000 (2) | −0.012 (3) |
C13 | 0.041 (3) | 0.096 (6) | 0.069 (4) | −0.001 (4) | −0.005 (3) | −0.035 (4) |
C14 | 0.051 (4) | 0.090 (6) | 0.095 (6) | −0.029 (4) | 0.014 (4) | −0.041 (5) |
C15 | 0.080 (6) | 0.061 (5) | 0.103 (6) | −0.035 (4) | 0.012 (5) | −0.013 (4) |
C16 | 0.049 (3) | 0.047 (3) | 0.072 (4) | −0.010 (3) | 0.004 (3) | −0.005 (3) |
C21 | 0.034 (2) | 0.030 (2) | 0.029 (2) | 0.0029 (19) | 0.0021 (18) | 0.0031 (18) |
C22 | 0.072 (4) | 0.038 (3) | 0.032 (3) | 0.010 (3) | 0.010 (2) | 0.003 (2) |
C23 | 0.102 (5) | 0.030 (3) | 0.044 (3) | 0.005 (3) | 0.012 (3) | 0.006 (2) |
C24 | 0.069 (4) | 0.044 (3) | 0.037 (3) | 0.001 (3) | 0.007 (3) | 0.012 (2) |
C25 | 0.061 (4) | 0.049 (3) | 0.024 (2) | −0.001 (3) | 0.005 (2) | 0.003 (2) |
C26 | 0.057 (3) | 0.033 (3) | 0.032 (2) | −0.002 (2) | 0.007 (2) | −0.0019 (19) |
C31 | 0.042 (3) | 0.030 (2) | 0.024 (2) | −0.001 (2) | 0.0036 (18) | 0.0017 (17) |
C32 | 0.044 (3) | 0.045 (3) | 0.044 (3) | −0.002 (2) | 0.009 (2) | −0.010 (2) |
C33 | 0.057 (4) | 0.055 (3) | 0.057 (4) | 0.004 (3) | 0.021 (3) | −0.015 (3) |
C34 | 0.082 (5) | 0.046 (3) | 0.043 (3) | 0.010 (3) | 0.010 (3) | −0.017 (2) |
C35 | 0.072 (4) | 0.038 (3) | 0.043 (3) | 0.003 (3) | −0.014 (3) | −0.008 (2) |
C36 | 0.044 (3) | 0.037 (3) | 0.037 (3) | 0.003 (2) | −0.002 (2) | −0.0008 (19) |
B1 | 0.041 (3) | 0.027 (2) | 0.031 (2) | −0.002 (2) | 0.004 (2) | −0.002 (2) |
Au1—P1 | 2.2557 (12) | C12—C13 | 1.393 (9) |
Au1—S2 | 2.3511 (12) | C12—H12 | 0.930 |
Au1—S1 | 2.8155 (13) | C13—C14 | 1.374 (12) |
S1—C1 | 1.707 (5) | C13—H13 | 0.930 |
S2—C5 | 1.725 (5) | C14—C15 | 1.359 (13) |
P1—C11 | 1.815 (5) | C14—H14 | 0.930 |
P1—C21 | 1.820 (5) | C15—C16 | 1.395 (10) |
P1—C31 | 1.825 (5) | C15—H15 | 0.930 |
N1—C1 | 1.352 (6) | C16—H16 | 0.930 |
N1—C2 | 1.387 (6) | C21—C22 | 1.379 (7) |
N1—B1 | 1.561 (6) | C21—C26 | 1.394 (7) |
N2—C1 | 1.360 (6) | C22—C23 | 1.390 (7) |
N2—C3 | 1.372 (7) | C22—H22 | 0.930 |
N2—C4 | 1.462 (6) | C23—C24 | 1.394 (8) |
N3—C5 | 1.344 (6) | C23—H23 | 0.930 |
N3—C6 | 1.379 (7) | C24—C25 | 1.373 (7) |
N3—B1 | 1.559 (7) | C24—H24 | 0.930 |
N4—C5 | 1.351 (6) | C25—C26 | 1.383 (7) |
N4—C7 | 1.383 (6) | C25—H25 | 0.930 |
N4—C8 | 1.458 (6) | C26—H26 | 0.930 |
C2—C3 | 1.345 (7) | C31—C32 | 1.368 (7) |
C2—H2 | 0.930 | C31—C36 | 1.382 (7) |
C3—H3 | 0.930 | C32—C33 | 1.391 (8) |
C4—H4A | 0.960 | C32—H32 | 0.930 |
C4—H4B | 0.960 | C33—C34 | 1.386 (9) |
C4—H4C | 0.960 | C33—H33 | 0.930 |
C6—C7 | 1.342 (7) | C34—C35 | 1.361 (10) |
C6—H6 | 0.930 | C34—H34 | 0.930 |
C7—H7 | 0.930 | C35—C36 | 1.403 (8) |
C8—H8A | 0.960 | C35—H35 | 0.930 |
C8—H8B | 0.960 | C36—H36 | 0.930 |
C8—H8C | 0.960 | B1—H1A | 0.970 |
C11—C12 | 1.373 (8) | B1—H1B | 0.970 |
C11—C16 | 1.395 (8) | ||
P1—Au1—S2 | 159.74 (4) | C11—C12—H12 | 119.4 |
P1—Au1—S1 | 98.78 (4) | C13—C12—H12 | 119.4 |
S2—Au1—S1 | 101.15 (4) | C14—C13—C12 | 119.0 (7) |
C1—S1—Au1 | 102.01 (16) | C14—C13—H13 | 120.5 |
C5—S2—Au1 | 103.69 (16) | C12—C13—H13 | 120.5 |
C11—P1—C21 | 106.2 (2) | C15—C14—C13 | 121.2 (7) |
C11—P1—C31 | 105.1 (2) | C15—C14—H14 | 119.4 |
C21—P1—C31 | 102.9 (2) | C13—C14—H14 | 119.4 |
C11—P1—Au1 | 112.17 (17) | C14—C15—C16 | 119.8 (8) |
C21—P1—Au1 | 114.20 (15) | C14—C15—H15 | 120.1 |
C31—P1—Au1 | 115.30 (16) | C16—C15—H15 | 120.1 |
C1—N1—C2 | 108.1 (4) | C11—C16—C15 | 120.0 (7) |
C1—N1—B1 | 127.7 (4) | C11—C16—H16 | 120.0 |
C2—N1—B1 | 123.8 (4) | C15—C16—H16 | 120.0 |
C1—N2—C3 | 109.3 (4) | C22—C21—C26 | 118.8 (4) |
C1—N2—C4 | 124.5 (5) | C22—C21—P1 | 123.2 (3) |
C3—N2—C4 | 126.2 (5) | C26—C21—P1 | 117.8 (4) |
C5—N3—C6 | 107.7 (4) | C21—C22—C23 | 120.7 (5) |
C5—N3—B1 | 129.8 (4) | C21—C22—H22 | 119.6 |
C6—N3—B1 | 122.3 (4) | C23—C22—H22 | 119.6 |
C5—N4—C7 | 108.6 (4) | C22—C23—C24 | 119.6 (5) |
C5—N4—C8 | 126.5 (4) | C22—C23—H23 | 120.2 |
C7—N4—C8 | 124.9 (4) | C24—C23—H23 | 120.2 |
N1—C1—N2 | 107.3 (4) | C25—C24—C23 | 120.0 (5) |
N1—C1—S1 | 128.1 (3) | C25—C24—H24 | 120.0 |
N2—C1—S1 | 124.6 (4) | C23—C24—H24 | 120.0 |
C3—C2—N1 | 108.3 (4) | C24—C25—C26 | 120.0 (5) |
C3—C2—H2 | 125.9 | C24—C25—H25 | 120.0 |
N1—C2—H2 | 125.9 | C26—C25—H25 | 120.0 |
C2—C3—N2 | 107.1 (4) | C25—C26—C21 | 120.8 (5) |
C2—C3—H3 | 126.4 | C25—C26—H26 | 119.6 |
N2—C3—H3 | 126.4 | C21—C26—H26 | 119.6 |
N2—C4—H4A | 109.5 | C32—C31—C36 | 119.9 (5) |
N2—C4—H4B | 109.5 | C32—C31—P1 | 122.9 (4) |
H4A—C4—H4B | 109.5 | C36—C31—P1 | 117.1 (4) |
N2—C4—H4C | 109.5 | C31—C32—C33 | 120.5 (5) |
H4A—C4—H4C | 109.5 | C31—C32—H32 | 119.7 |
H4B—C4—H4C | 109.5 | C33—C32—H32 | 119.7 |
N3—C5—N4 | 108.2 (4) | C34—C33—C32 | 119.5 (6) |
N3—C5—S2 | 130.0 (4) | C34—C33—H33 | 120.2 |
N4—C5—S2 | 121.8 (4) | C32—C33—H33 | 120.2 |
C7—C6—N3 | 108.8 (4) | C35—C34—C33 | 120.2 (5) |
C7—C6—H6 | 125.6 | C35—C34—H34 | 119.9 |
N3—C6—H6 | 125.6 | C33—C34—H34 | 119.9 |
C6—C7—N4 | 106.7 (5) | C34—C35—C36 | 120.2 (6) |
C6—C7—H7 | 126.7 | C34—C35—H35 | 119.9 |
N4—C7—H7 | 126.7 | C36—C35—H35 | 119.9 |
N4—C8—H8A | 109.5 | C31—C36—C35 | 119.6 (5) |
N4—C8—H8B | 109.5 | C31—C36—H36 | 120.2 |
H8A—C8—H8B | 109.5 | C35—C36—H36 | 120.2 |
N4—C8—H8C | 109.5 | N3—B1—N1 | 110.6 (4) |
H8A—C8—H8C | 109.5 | N3—B1—H1A | 109.5 |
H8B—C8—H8C | 109.5 | N1—B1—H1A | 109.5 |
C12—C11—C16 | 118.8 (5) | N3—B1—H1B | 109.5 |
C12—C11—P1 | 123.7 (4) | N1—B1—H1B | 109.5 |
C16—C11—P1 | 117.5 (4) | H1A—B1—H1B | 108.1 |
C11—C12—C13 | 121.1 (6) | ||
P1—Au1—S1—C1 | 84.63 (17) | C21—P1—C11—C16 | −151.5 (4) |
S2—Au1—S1—C1 | −99.07 (17) | C31—P1—C11—C16 | 99.9 (4) |
P1—Au1—S2—C5 | −159.23 (18) | Au1—P1—C11—C16 | −26.1 (5) |
S1—Au1—S2—C5 | 31.38 (17) | C16—C11—C12—C13 | −2.5 (8) |
S2—Au1—P1—C11 | 32.6 (2) | P1—C11—C12—C13 | 176.5 (5) |
S1—Au1—P1—C11 | −157.91 (17) | C11—C12—C13—C14 | 1.4 (10) |
S2—Au1—P1—C21 | 153.5 (2) | C12—C13—C14—C15 | 0.7 (12) |
S1—Au1—P1—C21 | −37.01 (18) | C13—C14—C15—C16 | −1.7 (13) |
S2—Au1—P1—C31 | −87.6 (2) | C12—C11—C16—C15 | 1.5 (9) |
S1—Au1—P1—C31 | 81.85 (17) | P1—C11—C16—C15 | −177.5 (6) |
C2—N1—C1—N2 | −0.7 (5) | C14—C15—C16—C11 | 0.6 (12) |
B1—N1—C1—N2 | 172.2 (4) | C11—P1—C21—C22 | −114.9 (5) |
C2—N1—C1—S1 | −180.0 (4) | C31—P1—C21—C22 | −4.8 (5) |
B1—N1—C1—S1 | −7.2 (7) | Au1—P1—C21—C22 | 120.9 (4) |
C3—N2—C1—N1 | 0.3 (5) | C11—P1—C21—C26 | 69.2 (4) |
C4—N2—C1—N1 | −178.5 (5) | C31—P1—C21—C26 | 179.4 (4) |
C3—N2—C1—S1 | 179.7 (4) | Au1—P1—C21—C26 | −54.9 (4) |
C4—N2—C1—S1 | 0.8 (8) | C26—C21—C22—C23 | −0.1 (9) |
Au1—S1—C1—N1 | 42.4 (4) | P1—C21—C22—C23 | −175.8 (5) |
Au1—S1—C1—N2 | −136.8 (4) | C21—C22—C23—C24 | −0.2 (10) |
C1—N1—C2—C3 | 0.8 (6) | C22—C23—C24—C25 | −0.1 (11) |
B1—N1—C2—C3 | −172.4 (5) | C23—C24—C25—C26 | 0.6 (10) |
N1—C2—C3—N2 | −0.6 (6) | C24—C25—C26—C21 | −0.8 (9) |
C1—N2—C3—C2 | 0.2 (6) | C22—C21—C26—C25 | 0.5 (8) |
C4—N2—C3—C2 | 179.0 (6) | P1—C21—C26—C25 | 176.6 (5) |
C6—N3—C5—N4 | 1.0 (5) | C11—P1—C31—C32 | 10.9 (5) |
B1—N3—C5—N4 | −173.7 (4) | C21—P1—C31—C32 | −100.1 (5) |
C6—N3—C5—S2 | 178.2 (4) | Au1—P1—C31—C32 | 134.9 (4) |
B1—N3—C5—S2 | 3.5 (7) | C11—P1—C31—C36 | −171.5 (4) |
C7—N4—C5—N3 | −1.1 (5) | C21—P1—C31—C36 | 77.5 (4) |
C8—N4—C5—N3 | 176.5 (5) | Au1—P1—C31—C36 | −47.4 (4) |
C7—N4—C5—S2 | −178.7 (4) | C36—C31—C32—C33 | 0.9 (8) |
C8—N4—C5—S2 | −1.0 (7) | P1—C31—C32—C33 | 178.6 (5) |
Au1—S2—C5—N3 | 36.0 (5) | C31—C32—C33—C34 | 0.0 (10) |
Au1—S2—C5—N4 | −147.1 (4) | C32—C33—C34—C35 | −1.7 (10) |
C5—N3—C6—C7 | −0.4 (6) | C33—C34—C35—C36 | 2.4 (10) |
B1—N3—C6—C7 | 174.7 (4) | C32—C31—C36—C35 | −0.2 (8) |
N3—C6—C7—N4 | −0.3 (6) | P1—C31—C36—C35 | −178.0 (4) |
C5—N4—C7—C6 | 0.9 (6) | C34—C35—C36—C31 | −1.5 (8) |
C8—N4—C7—C6 | −176.8 (5) | C5—N3—B1—N1 | −121.8 (5) |
C21—P1—C11—C12 | 29.6 (5) | C6—N3—B1—N1 | 64.2 (5) |
C31—P1—C11—C12 | −79.0 (5) | C1—N1—B1—N3 | 60.5 (6) |
Au1—P1—C11—C12 | 155.0 (4) | C2—N1—B1—N3 | −127.7 (5) |
Experimental details
Crystal data | |
Chemical formula | [Au(C8H12N4S2)(C18H15P)] |
Mr | 698.38 |
Crystal system, space group | Monoclinic, P21/c |
Temperature (K) | 110 |
a, b, c (Å) | 20.7037 (12), 8.6870 (5), 15.2487 (9) |
β (°) | 95.643 (1) |
V (Å3) | 2729.2 (3) |
Z | 4 |
Radiation type | Mo Kα |
µ (mm−1) | 5.62 |
Crystal size (mm) | 0.29 × 0.13 × 0.13 |
Data collection | |
Diffractometer | Bruker SMART area-detector diffractometer |
Absorption correction | Multi-scan (SADABS; Blessing, 1995) |
Tmin, Tmax | 0.351, 0.495 |
No. of measured, independent and observed [I > 2σ(I)] reflections | 17546, 6619, 5410 |
Rint | 0.087 |
(sin θ/λ)max (Å−1) | 0.667 |
Refinement | |
R[F2 > 2σ(F2)], wR(F2), S | 0.041, 0.110, 1.04 |
No. of reflections | 6619 |
No. of parameters | 319 |
H-atom treatment | H-atom parameters constrained |
Δρmax, Δρmin (e Å−3) | 1.86, −2.35 |
Computer programs: SMART (Bruker, 2001), SAINT (Bruker, 1999), SAINT, SHELXS97 (Sheldrick, 1990), SHELXL97 (Sheldrick, 1997), SHELXTL (Siemens, 1996), SHELXL97.
Au1—P1 | 2.2557 (12) | S2—C5 | 1.725 (5) |
Au1—S2 | 2.3511 (12) | N1—B1 | 1.561 (6) |
Au1—S1 | 2.8155 (13) | N3—B1 | 1.559 (7) |
S1—C1 | 1.707 (5) | ||
P1—Au1—S2 | 159.74 (4) | S2—Au1—S1 | 101.15 (4) |
P1—Au1—S1 | 98.78 (4) | N3—B1—N1 | 110.6 (4) |
The coordination chemistry of the nitrogen-donor poly(pyrazol-1-yl)borate ligands has been extensively investigated with various metals (Trofimenko, 1999; Parkin, 1995). Recently, the coordination of these ligands has been studied with coinage (group 11) metals (Santini et al., 1998; Effendy et al., 2000). Softer (sulfur) donor ligands were synthesized by the reaction of molten 2-thiol-1-methylimidazole (methimazole) with borohydride salts, to produce the hydrobis(methimazolyl)borate anion (abbreviated Bm) (Kimblin et al., 1997) or hydrotris(methimazolyl)borate anion (abbreviated Tm) (Garner et al., 1996). Poly(methimazolyl)borate complexes were suggested to be models of enzymes (Kimblin et al., 1997). Silver(I) complexes of Tm have been characterized, such as Cy3PAg(Tm) (Santini et al., 1999). We report here the first gold complex, (I), of a poly(methimazolyl)borate ligand, bis(2-mercapto-1-methylimidazolyl)borate (BmMe).
The unit cell of Ph3PAu(BmMe) contains four discrete symmetry-related molecules. The Au atom is coordinated in a distorted trigonal environment. The molecular structure is shown in Fig. 1, and selected bond distances and angles are given in Table 1. The P—Au—S angles are somewhat compressed [S1—Au1—P1 = 98.78 (4)°] and somehwat enlarged [P1—Au1—S2 = 159.74 (4)°]; the chelate angle at the Au atom, S1—Au1—S2, is 101.15 (4)°. The slight deviation of the sum of angles about the gold center from 360° is due to the displacement of Au1 by 0.048 Å from the AuS2P mean plane. The angles in the highly asymmetric eight-membered ring range from 101.15 (4)°, for S1—Au1—S2, to 130.0 (4)°, for S2—C5—N3.
The Au—Sthione distances are Au1—S1 = 2.8155 (12) Å and Au1—S2 = 2.3511 (12) Å. The C—S bond lengths of 1.707 (5) and 1.725 (5) Å are intermediate between single- and double-bond values. The Au—P distance, 2.2557 (12) Å, lies in the range observed for phosphine–gold complexes. The B atom is tetrahedrally coordinated. The thioimazolyl rings are approximately perpendicular to each other.