Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536806034118/er2015sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S1600536806034118/er2015Isup2.hkl |
CCDC reference: 620956
Data collection: COLLECT (Nonius, 2000); cell refinement: DENZO and SCALEPACK (Otwinowski & Minor, 1997); data reduction: DENZO and SCALEPACK; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997); software used to prepare material for publication: WinGX (Farrugia, 1999).
[Au(C10H11S2)(C18H15P)] | F(000) = 1280 |
Mr = 654.54 | Dx = 1.721 Mg m−3 |
Monoclinic, P21/n | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: -P 2yn | Cell parameters from 9809 reflections |
a = 8.9954 (10) Å | θ = 2.5–34.3° |
b = 20.745 (2) Å | µ = 6.07 mm−1 |
c = 13.553 (2) Å | T = 105 K |
β = 93.002 (5)° | Fragment, orange |
V = 2525.6 (5) Å3 | 0.20 × 0.15 × 0.12 mm |
Z = 4 |
Nonius KappaCCD (with an Oxford Cryosystems Cryostream coller) diffractometer | 8513 reflections with I > 2σ(I) |
ω scans with κ offsets | Rint = 0.024 |
Absorption correction: multi-scan (SCALEPACK; Otwinowski & Minor, 1997) | θmax = 34.3°, θmin = 2.7° |
Tmin = 0.431, Tmax = 0.530 | h = −14→14 |
48287 measured reflections | k = −32→25 |
10430 independent reflections | l = −21→21 |
Refinement on F2 | H-atom parameters constrained |
Least-squares matrix: full | w = 1/[σ2(Fo2) + (0.0096P)2 + 5.4333P] where P = (Fo2 + 2Fc2)/3 |
R[F2 > 2σ(F2)] = 0.027 | (Δ/σ)max = 0.001 |
wR(F2) = 0.054 | Δρmax = 0.84 e Å−3 |
S = 0.95 | Δρmin = −1.26 e Å−3 |
10430 reflections | Extinction correction: SHELXL97, Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4 |
293 parameters | Extinction coefficient: 0.00059 (5) |
0 restraints |
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. |
x | y | z | Uiso*/Ueq | ||
C1 | 0.0982 (3) | 0.26817 (11) | 0.38843 (18) | 0.0188 (4) | |
C2 | 0.0764 (3) | 0.24105 (11) | 0.28645 (17) | 0.0179 (4) | |
C3 | 0.1974 (3) | 0.23817 (11) | 0.22513 (17) | 0.0186 (4) | |
C4 | 0.1744 (3) | 0.21292 (12) | 0.13018 (17) | 0.0217 (4) | |
H4 | 0.2558 | 0.2112 | 0.0883 | 0.026* | |
C5 | 0.0363 (3) | 0.19012 (12) | 0.09493 (18) | 0.0250 (5) | |
C6 | −0.0819 (3) | 0.19473 (12) | 0.1563 (2) | 0.0260 (5) | |
H6 | −0.1774 | 0.1803 | 0.1324 | 0.031* | |
C7 | −0.0655 (3) | 0.21972 (12) | 0.25150 (19) | 0.0230 (5) | |
C8 | −0.1973 (3) | 0.22339 (15) | 0.3160 (2) | 0.0345 (6) | |
H8A | −0.2887 | 0.2134 | 0.2763 | 0.052* | |
H8B | −0.2043 | 0.2669 | 0.3434 | 0.052* | |
H8C | −0.1845 | 0.1922 | 0.37 | 0.052* | |
C9 | 0.3504 (3) | 0.26111 (13) | 0.25984 (19) | 0.0252 (5) | |
H9A | 0.4214 | 0.251 | 0.2096 | 0.038* | |
H9B | 0.3811 | 0.2394 | 0.3218 | 0.038* | |
H9C | 0.3483 | 0.3078 | 0.2706 | 0.038* | |
C10 | 0.0167 (4) | 0.16146 (16) | −0.0073 (2) | 0.0389 (7) | |
H10A | 0.0552 | 0.1173 | −0.0065 | 0.058* | |
H10B | 0.0715 | 0.1875 | −0.0537 | 0.058* | |
H10C | −0.0892 | 0.1611 | −0.0282 | 0.058* | |
C11 | −0.0137 (2) | −0.02173 (12) | 0.30954 (16) | 0.0181 (4) | |
C12 | −0.1261 (3) | 0.01353 (13) | 0.25845 (18) | 0.0239 (5) | |
H12 | −0.1112 | 0.0578 | 0.2439 | 0.029* | |
C13 | −0.2588 (3) | −0.01630 (15) | 0.22914 (18) | 0.0277 (5) | |
H13 | −0.3344 | 0.0074 | 0.1937 | 0.033* | |
C14 | −0.2820 (3) | −0.08079 (15) | 0.25134 (19) | 0.0287 (6) | |
H14 | −0.373 | −0.1011 | 0.2307 | 0.034* | |
C15 | −0.1719 (3) | −0.11554 (14) | 0.30378 (19) | 0.0265 (5) | |
H15 | −0.1885 | −0.1594 | 0.3199 | 0.032* | |
C16 | −0.0374 (3) | −0.08619 (12) | 0.33286 (17) | 0.0210 (4) | |
H16 | 0.038 | −0.11 | 0.3684 | 0.025* | |
C17 | 0.2805 (2) | −0.03747 (11) | 0.40625 (16) | 0.0163 (4) | |
C18 | 0.2961 (3) | −0.03155 (12) | 0.50900 (17) | 0.0218 (5) | |
H18 | 0.2467 | 0.0022 | 0.5415 | 0.026* | |
C19 | 0.3842 (3) | −0.07527 (14) | 0.56361 (18) | 0.0268 (5) | |
H19 | 0.3947 | −0.0715 | 0.6335 | 0.032* | |
C20 | 0.4570 (3) | −0.12441 (12) | 0.51588 (19) | 0.0227 (5) | |
H20 | 0.5163 | −0.1544 | 0.5534 | 0.027* | |
C21 | 0.4434 (3) | −0.12987 (11) | 0.41408 (18) | 0.0205 (4) | |
H21 | 0.4945 | −0.1632 | 0.3818 | 0.025* | |
C22 | 0.3551 (3) | −0.08661 (11) | 0.35878 (17) | 0.0190 (4) | |
H22 | 0.3455 | −0.0905 | 0.2889 | 0.023* | |
C23 | 0.2391 (3) | 0.02826 (11) | 0.21741 (16) | 0.0181 (4) | |
C24 | 0.1909 (3) | −0.00917 (12) | 0.13649 (17) | 0.0235 (5) | |
H24 | 0.1172 | −0.0414 | 0.1439 | 0.028* | |
C25 | 0.2504 (3) | 0.00051 (13) | 0.04477 (18) | 0.0262 (5) | |
H25 | 0.2168 | −0.0247 | −0.0105 | 0.031* | |
C26 | 0.3595 (3) | 0.04743 (13) | 0.03442 (18) | 0.0247 (5) | |
H26 | 0.4 | 0.0541 | −0.0281 | 0.03* | |
C27 | 0.4089 (3) | 0.08423 (12) | 0.11441 (19) | 0.0235 (5) | |
H27 | 0.4842 | 0.1157 | 0.1071 | 0.028* | |
C28 | 0.3484 (3) | 0.07515 (12) | 0.20598 (17) | 0.0204 (4) | |
H28 | 0.3815 | 0.1009 | 0.2608 | 0.024* | |
Au | 0.138235 (10) | 0.115470 (4) | 0.412664 (6) | 0.01810 (3) | |
P | 0.16194 (7) | 0.01887 (3) | 0.33764 (4) | 0.01595 (10) | |
S2 | 0.09834 (8) | 0.34686 (3) | 0.40662 (5) | 0.02592 (13) | |
S1 | 0.12370 (8) | 0.21582 (3) | 0.48633 (4) | 0.02577 (13) |
U11 | U22 | U33 | U12 | U13 | U23 | |
C1 | 0.0207 (10) | 0.0153 (9) | 0.0206 (10) | 0.0038 (8) | 0.0019 (8) | 0.0018 (8) |
C2 | 0.0203 (10) | 0.0151 (9) | 0.0180 (10) | 0.0017 (8) | −0.0013 (8) | 0.0044 (8) |
C3 | 0.0192 (10) | 0.0180 (10) | 0.0183 (10) | 0.0020 (8) | −0.0011 (8) | 0.0030 (8) |
C4 | 0.0259 (11) | 0.0215 (10) | 0.0175 (10) | 0.0044 (9) | −0.0013 (9) | 0.0029 (8) |
C5 | 0.0345 (13) | 0.0196 (11) | 0.0199 (11) | 0.0027 (10) | −0.0102 (9) | 0.0012 (9) |
C6 | 0.0235 (12) | 0.0218 (11) | 0.0313 (13) | −0.0011 (9) | −0.0106 (10) | 0.0065 (10) |
C7 | 0.0204 (11) | 0.0216 (11) | 0.0266 (12) | −0.0006 (9) | −0.0025 (9) | 0.0061 (9) |
C8 | 0.0207 (12) | 0.0400 (16) | 0.0431 (17) | −0.0004 (11) | 0.0040 (11) | 0.0080 (13) |
C9 | 0.0198 (11) | 0.0313 (13) | 0.0243 (12) | −0.0014 (10) | 0.0000 (9) | −0.0002 (10) |
C10 | 0.0516 (19) | 0.0374 (16) | 0.0259 (14) | 0.0038 (14) | −0.0159 (13) | −0.0068 (12) |
C11 | 0.0165 (9) | 0.0258 (11) | 0.0123 (9) | 0.0019 (8) | 0.0020 (7) | −0.0003 (8) |
C12 | 0.0250 (11) | 0.0293 (12) | 0.0173 (10) | 0.0074 (10) | 0.0016 (9) | 0.0024 (9) |
C13 | 0.0208 (11) | 0.0449 (16) | 0.0173 (11) | 0.0066 (11) | −0.0006 (9) | 0.0009 (10) |
C14 | 0.0202 (11) | 0.0466 (16) | 0.0193 (11) | −0.0040 (11) | 0.0009 (9) | −0.0003 (11) |
C15 | 0.0265 (12) | 0.0323 (13) | 0.0207 (11) | −0.0066 (11) | 0.0004 (9) | 0.0024 (10) |
C16 | 0.0216 (11) | 0.0261 (11) | 0.0153 (10) | −0.0005 (9) | 0.0015 (8) | 0.0026 (8) |
C17 | 0.0158 (9) | 0.0178 (9) | 0.0152 (9) | 0.0001 (8) | 0.0002 (7) | 0.0003 (7) |
C18 | 0.0242 (11) | 0.0262 (11) | 0.0151 (10) | 0.0054 (9) | 0.0019 (8) | −0.0002 (8) |
C19 | 0.0306 (13) | 0.0345 (13) | 0.0152 (10) | 0.0092 (11) | 0.0005 (9) | 0.0034 (9) |
C20 | 0.0201 (10) | 0.0234 (11) | 0.0241 (11) | 0.0046 (9) | −0.0023 (9) | 0.0050 (9) |
C21 | 0.0197 (10) | 0.0171 (10) | 0.0249 (11) | 0.0010 (8) | 0.0029 (9) | −0.0004 (8) |
C22 | 0.0205 (10) | 0.0192 (10) | 0.0172 (10) | 0.0002 (8) | 0.0012 (8) | −0.0014 (8) |
C23 | 0.0225 (10) | 0.0185 (10) | 0.0133 (9) | 0.0052 (8) | 0.0022 (8) | 0.0025 (8) |
C24 | 0.0309 (12) | 0.0234 (11) | 0.0164 (10) | −0.0010 (10) | 0.0042 (9) | −0.0007 (9) |
C25 | 0.0353 (13) | 0.0268 (12) | 0.0168 (11) | 0.0000 (11) | 0.0056 (10) | −0.0025 (9) |
C26 | 0.0280 (12) | 0.0295 (12) | 0.0174 (10) | 0.0061 (10) | 0.0081 (9) | 0.0051 (9) |
C27 | 0.0224 (11) | 0.0255 (12) | 0.0229 (11) | 0.0033 (9) | 0.0047 (9) | 0.0045 (9) |
C28 | 0.0212 (10) | 0.0223 (10) | 0.0177 (10) | 0.0022 (9) | −0.0002 (8) | 0.0024 (8) |
Au | 0.02475 (4) | 0.01548 (4) | 0.01414 (4) | 0.00363 (3) | 0.00162 (3) | 0.00069 (3) |
P | 0.0191 (3) | 0.0162 (2) | 0.0126 (2) | 0.0024 (2) | 0.00190 (19) | 0.00081 (19) |
S2 | 0.0371 (3) | 0.0168 (2) | 0.0241 (3) | 0.0055 (2) | 0.0038 (3) | 0.0001 (2) |
S1 | 0.0453 (4) | 0.0168 (2) | 0.0152 (2) | 0.0053 (3) | 0.0012 (2) | −0.0002 (2) |
C1—C2 | 1.496 (3) | C14—H14 | 0.95 |
C1—S2 | 1.651 (2) | C15—C16 | 1.393 (3) |
C1—S1 | 1.721 (2) | C15—H15 | 0.95 |
C2—C3 | 1.405 (3) | C16—H16 | 0.95 |
C2—C7 | 1.409 (3) | C17—C22 | 1.396 (3) |
C3—C4 | 1.395 (3) | C17—C18 | 1.398 (3) |
C3—C9 | 1.509 (3) | C17—P | 1.807 (2) |
C4—C5 | 1.391 (4) | C18—C19 | 1.392 (3) |
C4—H4 | 0.95 | C18—H18 | 0.95 |
C5—C6 | 1.386 (4) | C19—C20 | 1.389 (4) |
C5—C10 | 1.510 (4) | C19—H19 | 0.95 |
C6—C7 | 1.392 (4) | C20—C21 | 1.383 (3) |
C6—H6 | 0.95 | C20—H20 | 0.95 |
C7—C8 | 1.512 (4) | C21—C22 | 1.391 (3) |
C8—H8A | 0.98 | C21—H21 | 0.95 |
C8—H8B | 0.98 | C22—H22 | 0.95 |
C8—H8C | 0.98 | C23—C24 | 1.394 (3) |
C9—H9A | 0.98 | C23—C28 | 1.397 (3) |
C9—H9B | 0.98 | C23—P | 1.815 (2) |
C9—H9C | 0.98 | C24—C25 | 1.393 (3) |
C10—H10A | 0.98 | C24—H24 | 0.95 |
C10—H10B | 0.98 | C25—C26 | 1.394 (4) |
C10—H10C | 0.98 | C25—H25 | 0.95 |
C11—C16 | 1.393 (3) | C26—C27 | 1.380 (4) |
C11—C12 | 1.401 (3) | C26—H26 | 0.95 |
C11—P | 1.813 (2) | C27—C28 | 1.394 (3) |
C12—C13 | 1.385 (4) | C27—H27 | 0.95 |
C12—H12 | 0.95 | C28—H28 | 0.95 |
C13—C14 | 1.389 (4) | Au—P | 2.2623 (6) |
C13—H13 | 0.95 | Au—S1 | 2.3155 (6) |
C14—C15 | 1.390 (4) | ||
C2—C1—S2 | 120.59 (17) | C14—C15—C16 | 120.2 (3) |
C2—C1—S1 | 118.75 (16) | C14—C15—H15 | 119.9 |
S2—C1—S1 | 120.66 (15) | C16—C15—H15 | 119.9 |
C3—C2—C7 | 120.2 (2) | C11—C16—C15 | 119.7 (2) |
C3—C2—C1 | 119.6 (2) | C11—C16—H16 | 120.1 |
C7—C2—C1 | 120.1 (2) | C15—C16—H16 | 120.1 |
C4—C3—C2 | 118.7 (2) | C22—C17—C18 | 119.9 (2) |
C4—C3—C9 | 119.6 (2) | C22—C17—P | 121.35 (17) |
C2—C3—C9 | 121.7 (2) | C18—C17—P | 118.79 (17) |
C5—C4—C3 | 122.1 (2) | C19—C18—C17 | 119.8 (2) |
C5—C4—H4 | 119 | C19—C18—H18 | 120.1 |
C3—C4—H4 | 119 | C17—C18—H18 | 120.1 |
C6—C5—C4 | 118.0 (2) | C20—C19—C18 | 120.0 (2) |
C6—C5—C10 | 121.4 (3) | C20—C19—H19 | 120 |
C4—C5—C10 | 120.5 (3) | C18—C19—H19 | 120 |
C5—C6—C7 | 122.3 (2) | C21—C20—C19 | 120.4 (2) |
C5—C6—H6 | 118.8 | C21—C20—H20 | 119.8 |
C7—C6—H6 | 118.8 | C19—C20—H20 | 119.8 |
C6—C7—C2 | 118.6 (2) | C20—C21—C22 | 120.2 (2) |
C6—C7—C8 | 120.5 (2) | C20—C21—H21 | 119.9 |
C2—C7—C8 | 120.9 (2) | C22—C21—H21 | 119.9 |
C7—C8—H8A | 109.5 | C21—C22—C17 | 119.8 (2) |
C7—C8—H8B | 109.5 | C21—C22—H22 | 120.1 |
H8A—C8—H8B | 109.5 | C17—C22—H22 | 120.1 |
C7—C8—H8C | 109.5 | C24—C23—C28 | 119.5 (2) |
H8A—C8—H8C | 109.5 | C24—C23—P | 121.89 (18) |
H8B—C8—H8C | 109.5 | C28—C23—P | 118.60 (18) |
C3—C9—H9A | 109.5 | C23—C24—C25 | 120.2 (2) |
C3—C9—H9B | 109.5 | C23—C24—H24 | 119.9 |
H9A—C9—H9B | 109.5 | C25—C24—H24 | 119.9 |
C3—C9—H9C | 109.5 | C24—C25—C26 | 119.7 (2) |
H9A—C9—H9C | 109.5 | C24—C25—H25 | 120.1 |
H9B—C9—H9C | 109.5 | C26—C25—H25 | 120.1 |
C5—C10—H10A | 109.5 | C27—C26—C25 | 120.4 (2) |
C5—C10—H10B | 109.5 | C27—C26—H26 | 119.8 |
H10A—C10—H10B | 109.5 | C25—C26—H26 | 119.8 |
C5—C10—H10C | 109.5 | C26—C27—C28 | 120.0 (2) |
H10A—C10—H10C | 109.5 | C26—C27—H27 | 120 |
H10B—C10—H10C | 109.5 | C28—C27—H27 | 120 |
C16—C11—C12 | 119.9 (2) | C27—C28—C23 | 120.2 (2) |
C16—C11—P | 122.68 (18) | C27—C28—H28 | 119.9 |
C12—C11—P | 117.35 (19) | C23—C28—H28 | 119.9 |
C13—C12—C11 | 119.8 (2) | P—Au—S1 | 177.43 (2) |
C13—C12—H12 | 120.1 | C17—P—C11 | 106.99 (11) |
C11—C12—H12 | 120.1 | C17—P—C23 | 106.74 (10) |
C12—C13—C14 | 120.3 (2) | C11—P—C23 | 103.38 (11) |
C12—C13—H13 | 119.8 | C17—P—Au | 114.12 (8) |
C14—C13—H13 | 119.8 | C11—P—Au | 113.84 (8) |
C15—C14—C13 | 120.0 (2) | C23—P—Au | 110.97 (8) |
C15—C14—H14 | 120 | C1—S1—Au | 104.07 (8) |
C13—C14—H14 | 120 | ||
S2—C1—C2—C3 | 81.1 (3) | C19—C20—C21—C22 | −0.9 (4) |
S1—C1—C2—C3 | −98.7 (2) | C20—C21—C22—C17 | 0.3 (3) |
S2—C1—C2—C7 | −97.6 (2) | C18—C17—C22—C21 | 0.6 (3) |
S1—C1—C2—C7 | 82.5 (3) | P—C17—C22—C21 | −178.83 (17) |
C7—C2—C3—C4 | −1.0 (3) | C28—C23—C24—C25 | −0.5 (4) |
C1—C2—C3—C4 | −179.8 (2) | P—C23—C24—C25 | 178.5 (2) |
C7—C2—C3—C9 | 179.5 (2) | C23—C24—C25—C26 | 0.6 (4) |
C1—C2—C3—C9 | 0.7 (3) | C24—C25—C26—C27 | 0.1 (4) |
C2—C3—C4—C5 | −0.6 (3) | C25—C26—C27—C28 | −0.8 (4) |
C9—C3—C4—C5 | 178.9 (2) | C26—C27—C28—C23 | 0.9 (4) |
C3—C4—C5—C6 | 1.8 (4) | C24—C23—C28—C27 | −0.2 (4) |
C3—C4—C5—C10 | −178.3 (2) | P—C23—C28—C27 | −179.26 (18) |
C4—C5—C6—C7 | −1.6 (4) | C22—C17—P—C11 | 79.1 (2) |
C10—C5—C6—C7 | 178.6 (2) | C18—C17—P—C11 | −100.3 (2) |
C5—C6—C7—C2 | 0.1 (4) | C22—C17—P—C23 | −31.0 (2) |
C5—C6—C7—C8 | −179.6 (2) | C18—C17—P—C23 | 149.52 (19) |
C3—C2—C7—C6 | 1.3 (3) | C22—C17—P—Au | −154.00 (16) |
C1—C2—C7—C6 | −180.0 (2) | C18—C17—P—Au | 26.6 (2) |
C3—C2—C7—C8 | −179.1 (2) | C16—C11—P—C17 | −4.6 (2) |
C1—C2—C7—C8 | −0.3 (3) | C12—C11—P—C17 | 178.27 (17) |
C16—C11—C12—C13 | −1.6 (3) | C16—C11—P—C23 | 107.92 (19) |
P—C11—C12—C13 | 175.63 (18) | C12—C11—P—C23 | −69.24 (19) |
C11—C12—C13—C14 | 0.9 (4) | C16—C11—P—Au | −131.59 (17) |
C12—C13—C14—C15 | 0.4 (4) | C12—C11—P—Au | 51.24 (19) |
C13—C14—C15—C16 | −1.0 (4) | C24—C23—P—C17 | 93.1 (2) |
C12—C11—C16—C15 | 1.0 (3) | C28—C23—P—C17 | −87.9 (2) |
P—C11—C16—C15 | −176.06 (18) | C24—C23—P—C11 | −19.6 (2) |
C14—C15—C16—C11 | 0.3 (4) | C28—C23—P—C11 | 159.41 (18) |
C22—C17—C18—C19 | −0.9 (4) | C24—C23—P—Au | −142.03 (18) |
P—C17—C18—C19 | 178.6 (2) | C28—C23—P—Au | 37.0 (2) |
C17—C18—C19—C20 | 0.3 (4) | C2—C1—S1—Au | 5.9 (2) |
C18—C19—C20—C21 | 0.6 (4) | S2—C1—S1—Au | −173.97 (12) |