Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S0108270110016550/lg3031sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S0108270110016550/lg3031Isup2.hkl |
CCDC reference: 782524
For related literature, see: Baidya et al. (1991); Fantl et al. (1987); Garbauskas et al. (1983); Jensen (2004); Konno et al. (2009); Kovbasyuk et al. (1997); LeBlanc, Britten, Wang, Howard-Lock & Lock (1997); Schmidbaur & Schier (2008); Schmitt et al. (2002); Shi et al. (2006); Taguchi et al. (2007); Toyota et al. (2005).
A solution containing 0.013 g (0.04 mmol) of Ni(NO3)2.6H2O in 6 cm3 of ethanol was layered onto a colourless solution containing 0.050 g (0.09 mmol) of NH4[Au(D-Hpen)2].3.5H2O (LeBlanc et al., 1997; Konno et al., 2009) and 0.024 g (0.18 mmol) of K2CO3 in 1 cm3 of water in a test tube (1.5 cm × 10 cm), which was left in a refrigerator for 2 months. The resulting red, plate crystals of (I) were collected by filtration. IR (KBr, cm–1): 1593 (s, υas of OCO-).
H atoms bound to C and N atoms were placed at calculated positions [C—H = 0.98 (CH3), 0.99 (CH2) and 1.00 (CH), and N—H = 0.91 (NH3+), 0.92 (NH2) and 0.88 (NH)] and refined as riding with Uiso(H) = 1.2Ueq(C, N) for CH2, CH, NH2 and NH and 1.5Ueq(C, N) for CH3 and NH3+. Each of two ethanol molecules shares the same site with a water molecule, and these disordered molecules were refined with occupancies of 0.5. H atoms of water molecules and H atoms bound to O atoms of ethanol molecules were placed so as to form reasonable hydrogen bonding, except for two H atoms of disordered water molecules that were not included in the model. All H atoms bound to O atoms were refined with restrained geometric and displacement parameters [O—H = 0.85 (5) Å, H···H = 1.38 (5) Å and Uiso(H) = 1.2Ueq(O)]. In addition, 14 H atoms (H15A, H15B, H16B, H17A, H18A, H18B, H19A, H21A, H21B, H22B, H23A, H23B, H24, and H25) were refined with the restrained parameters so as to form reasonable hydrogen bonding.
Data collection: PROCESS-AUTO (Rigaku, 1998); cell refinement: PROCESS-AUTO (Rigaku, 1998); data reduction: CrystalStructure (Rigaku/MSC, 2004); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: Mercury (Macrae et al., 2006); software used to prepare material for publication: publCIF (Westrip, 2010).
K4[Au4Ni2(C6H8NO4S)(C5H9NO2S)4(C5H10NO2S)]·C2H6O·10H2O | F(000) = 2128 |
Mr = 2214.06 | Dx = 2.236 Mg m−3 |
Monoclinic, P21 | Mo Kα radiation, λ = 0.71075 Å |
Hall symbol: P 2yb | Cell parameters from 34450 reflections |
a = 9.9638 (18) Å | θ = 3.0–30.1° |
b = 22.644 (4) Å | µ = 9.97 mm−1 |
c = 14.723 (3) Å | T = 200 K |
β = 97.998 (7)° | Needle, red |
V = 3289.5 (10) Å3 | 0.15 × 0.15 × 0.04 mm |
Z = 2 |
Rigaku RAXIS-RAPID diffractometer | 17713 independent reflections |
Radiation source: fine-focus sealed tube | 16029 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.044 |
Detector resolution: 10.00 pixels mm-1 | θmax = 30.0°, θmin = 3.0° |
ω scans | h = −14→14 |
Absorption correction: multi-scan (ABSCOR; Higashi, 1995) | k = −31→29 |
Tmin = 0.316, Tmax = 0.691 | l = −20→20 |
38154 measured reflections |
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)] = 0.030 | H atoms treated by a mixture of independent and constrained refinement |
wR(F2) = 0.064 | w = 1/[σ2(Fo2) + (0.0056P)2] where P = (Fo2 + 2Fc2)/3 |
S = 1.04 | (Δ/σ)max = 0.001 |
17713 reflections | Δρmax = 1.14 e Å−3 |
804 parameters | Δρmin = −0.97 e Å−3 |
49 restraints | Absolute structure: Flack (1983). 8079 Friedel Pairs |
Primary atom site location: structure-invariant direct methods | Absolute structure parameter: −0.005 (3) |
K4[Au4Ni2(C6H8NO4S)(C5H9NO2S)4(C5H10NO2S)]·C2H6O·10H2O | V = 3289.5 (10) Å3 |
Mr = 2214.06 | Z = 2 |
Monoclinic, P21 | Mo Kα radiation |
a = 9.9638 (18) Å | µ = 9.97 mm−1 |
b = 22.644 (4) Å | T = 200 K |
c = 14.723 (3) Å | 0.15 × 0.15 × 0.04 mm |
β = 97.998 (7)° |
Rigaku RAXIS-RAPID diffractometer | 17713 independent reflections |
Absorption correction: multi-scan (ABSCOR; Higashi, 1995) | 16029 reflections with I > 2σ(I) |
Tmin = 0.316, Tmax = 0.691 | Rint = 0.044 |
38154 measured reflections |
R[F2 > 2σ(F2)] = 0.030 | H atoms treated by a mixture of independent and constrained refinement |
wR(F2) = 0.064 | Δρmax = 1.14 e Å−3 |
S = 1.04 | Δρmin = −0.97 e Å−3 |
17713 reflections | Absolute structure: Flack (1983). 8079 Friedel Pairs |
804 parameters | Absolute structure parameter: −0.005 (3) |
49 restraints |
Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds 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 | Occ. (<1) | |
Au1 | 0.036567 (19) | 0.253734 (9) | −0.081657 (17) | 0.01710 (5) | |
Au2 | 0.20358 (2) | 0.157111 (10) | 0.027257 (17) | 0.02000 (5) | |
Au3 | 0.19825 (2) | 0.370953 (10) | −0.017873 (17) | 0.02010 (5) | |
Au4 | 0.15529 (2) | 0.278386 (9) | 0.126191 (17) | 0.01696 (5) | |
Ni1 | −0.08065 (6) | 0.14333 (3) | −0.14709 (6) | 0.01478 (15) | |
Ni2 | 0.10443 (7) | 0.40292 (3) | 0.21117 (6) | 0.01450 (15) | |
K1 | −0.27872 (12) | 0.27266 (6) | 0.54363 (11) | 0.0257 (3) | |
K2 | −0.33196 (13) | 0.42437 (6) | 0.42523 (12) | 0.0259 (3) | |
K3 | −0.01420 (15) | 0.13962 (6) | 0.51312 (13) | 0.0361 (4) | |
K4 | 0.35920 (12) | 0.14745 (6) | −0.36847 (12) | 0.0290 (4) | |
S1 | −0.13567 (13) | 0.19568 (6) | −0.03508 (11) | 0.0173 (3) | |
S2 | 0.06493 (13) | 0.09054 (6) | −0.05895 (11) | 0.0183 (3) | |
S3 | 0.16598 (14) | 0.44096 (6) | 0.08863 (11) | 0.0179 (3) | |
S4 | −0.03057 (13) | 0.33741 (6) | 0.13872 (11) | 0.0155 (3) | |
S5 | 0.21126 (14) | 0.30517 (6) | −0.13551 (12) | 0.0195 (3) | |
S6 | 0.34522 (14) | 0.22088 (6) | 0.11829 (12) | 0.0196 (3) | |
O1 | −0.4449 (4) | 0.22462 (18) | −0.3265 (3) | 0.0272 (11) | |
O2 | −0.4855 (4) | 0.2939 (2) | −0.2276 (4) | 0.0383 (13) | |
O3 | 0.1587 (4) | 0.07034 (17) | −0.3673 (3) | 0.0193 (9) | |
O4 | 0.1549 (4) | −0.02365 (17) | −0.3199 (3) | 0.0255 (10) | |
O5 | 0.4781 (4) | 0.5024 (2) | 0.3511 (4) | 0.0359 (13) | |
O6 | 0.4261 (4) | 0.58590 (18) | 0.2775 (4) | 0.0403 (15) | |
O7 | −0.1183 (4) | 0.34293 (18) | 0.4495 (3) | 0.0248 (10) | |
O8 | −0.0449 (4) | 0.25043 (19) | 0.4410 (3) | 0.0280 (11) | |
O9 | 0.1387 (4) | 0.20511 (17) | −0.3156 (4) | 0.0264 (11) | |
O10 | −0.0610 (4) | 0.2510 (2) | −0.3291 (3) | 0.0302 (11) | |
O11 | 0.4599 (4) | 0.17817 (19) | 0.4469 (4) | 0.0301 (11) | |
O12 | 0.6534 (4) | 0.1747 (2) | 0.3882 (3) | 0.0319 (11) | |
O13 | 0.5414 (4) | 0.31679 (18) | 0.4114 (3) | 0.0261 (11) | |
O14 | 0.3345 (4) | 0.35605 (18) | 0.3859 (3) | 0.0268 (11) | |
N1 | −0.2233 (4) | 0.1831 (2) | −0.2258 (4) | 0.0187 (11) | |
H1A | −0.1896 | 0.1937 | −0.2785 | 0.022* | |
H1B | −0.2915 | 0.1561 | −0.2422 | 0.022* | |
N2 | −0.0150 (4) | 0.1054 (2) | −0.2506 (4) | 0.0179 (11) | |
H2A | −0.0882 | 0.0974 | −0.2941 | 0.022* | |
H2B | 0.0392 | 0.1319 | −0.2760 | 0.022* | |
N3 | 0.2318 (4) | 0.45634 (19) | 0.2793 (4) | 0.0173 (11) | |
H3A | 0.1876 | 0.4754 | 0.3217 | 0.021* | |
H3B | 0.2994 | 0.4340 | 0.3115 | 0.021* | |
N4 | 0.0462 (4) | 0.3773 (2) | 0.3223 (4) | 0.0186 (11) | |
H4A | 0.1181 | 0.3803 | 0.3686 | 0.022* | |
H4B | −0.0202 | 0.4027 | 0.3362 | 0.022* | |
N5 | 0.2732 (4) | 0.3017 (2) | −0.3517 (4) | 0.0183 (10) | |
H5A | 0.2993 | 0.3352 | −0.3786 | 0.027* | |
H5B | 0.2706 | 0.2711 | −0.3921 | 0.027* | |
H5C | 0.3334 | 0.2934 | −0.3010 | 0.027* | |
N6 | 0.3743 (4) | 0.2680 (2) | 0.3245 (4) | 0.0221 (12) | |
H6 | 0.2867 | 0.2644 | 0.3068 | 0.027* | |
C1 | −0.2998 (5) | 0.2279 (3) | −0.0895 (5) | 0.0186 (13) | |
C2 | −0.2859 (5) | 0.2368 (2) | −0.1901 (4) | 0.0152 (12) | |
H2 | −0.2211 | 0.2702 | −0.1934 | 0.018* | |
C3 | −0.4172 (5) | 0.2525 (3) | −0.2536 (5) | 0.0226 (14) | |
C4 | −0.4122 (5) | 0.1845 (3) | −0.0765 (6) | 0.0277 (16) | |
H41 | −0.5005 | 0.2029 | −0.0964 | 0.042* | |
H42 | −0.4056 | 0.1736 | −0.0116 | 0.042* | |
H43 | −0.4030 | 0.1490 | −0.1132 | 0.042* | |
C5 | −0.3206 (6) | 0.2850 (3) | −0.0422 (5) | 0.0261 (15) | |
H51 | −0.2554 | 0.3143 | −0.0583 | 0.039* | |
H52 | −0.3069 | 0.2789 | 0.0243 | 0.039* | |
H53 | −0.4130 | 0.2993 | −0.0617 | 0.039* | |
C6 | 0.1673 (5) | 0.0581 (2) | −0.1426 (4) | 0.0187 (12) | |
C7 | 0.0633 (5) | 0.0496 (2) | −0.2304 (4) | 0.0150 (11) | |
H7 | −0.0018 | 0.0181 | −0.2177 | 0.018* | |
C8 | 0.1314 (5) | 0.0298 (3) | −0.3141 (4) | 0.0170 (12) | |
C9 | 0.2821 (5) | 0.0991 (3) | −0.1609 (5) | 0.0244 (14) | |
H91 | 0.3437 | 0.1055 | −0.1037 | 0.037* | |
H92 | 0.2443 | 0.1371 | −0.1840 | 0.037* | |
H93 | 0.3321 | 0.0811 | −0.2066 | 0.037* | |
C10 | 0.2210 (6) | −0.0010 (3) | −0.1050 (5) | 0.0291 (16) | |
H101 | 0.2757 | −0.0191 | −0.1479 | 0.044* | |
H102 | 0.1448 | −0.0270 | −0.0972 | 0.044* | |
H103 | 0.2772 | 0.0049 | −0.0455 | 0.044* | |
C11 | 0.3328 (5) | 0.4727 (2) | 0.1391 (4) | 0.0176 (12) | |
C12 | 0.2958 (5) | 0.5011 (2) | 0.2289 (4) | 0.0171 (12) | |
H12 | 0.2251 | 0.5317 | 0.2097 | 0.020* | |
C13 | 0.4122 (6) | 0.5328 (2) | 0.2899 (5) | 0.0227 (14) | |
C14 | 0.4391 (6) | 0.4235 (3) | 0.1616 (5) | 0.0267 (16) | |
H141 | 0.4568 | 0.4045 | 0.1047 | 0.040* | |
H142 | 0.4047 | 0.3941 | 0.2015 | 0.040* | |
H143 | 0.5233 | 0.4406 | 0.1931 | 0.040* | |
C15 | 0.3741 (6) | 0.5182 (3) | 0.0756 (6) | 0.0337 (18) | |
H151 | 0.4479 | 0.5421 | 0.1078 | 0.051* | |
H152 | 0.2966 | 0.5438 | 0.0545 | 0.051* | |
H153 | 0.4050 | 0.4988 | 0.0228 | 0.051* | |
C16 | −0.1101 (5) | 0.3065 (2) | 0.2356 (5) | 0.0194 (13) | |
C17 | −0.0071 (5) | 0.3163 (2) | 0.3215 (4) | 0.0164 (12) | |
H17 | 0.0709 | 0.2892 | 0.3168 | 0.020* | |
C18 | −0.0599 (5) | 0.3019 (3) | 0.4135 (4) | 0.0169 (12) | |
C19 | −0.2406 (5) | 0.3413 (3) | 0.2372 (5) | 0.0241 (14) | |
H191 | −0.2965 | 0.3386 | 0.1771 | 0.036* | |
H192 | −0.2185 | 0.3828 | 0.2512 | 0.036* | |
H193 | −0.2905 | 0.3250 | 0.2843 | 0.036* | |
C20 | −0.1394 (6) | 0.2410 (2) | 0.2192 (5) | 0.0246 (14) | |
H201 | −0.1745 | 0.2242 | 0.2726 | 0.037* | |
H202 | −0.0557 | 0.2206 | 0.2100 | 0.037* | |
H203 | −0.2069 | 0.2362 | 0.1646 | 0.037* | |
C21 | 0.1400 (5) | 0.3490 (2) | −0.2381 (5) | 0.0198 (13) | |
C22 | 0.1354 (5) | 0.3106 (2) | −0.3246 (4) | 0.0153 (11) | |
H22 | 0.0818 | 0.3332 | −0.3755 | 0.018* | |
C23 | 0.0657 (5) | 0.2503 (3) | −0.3213 (5) | 0.0218 (13) | |
C24 | 0.2353 (6) | 0.4017 (3) | −0.2434 (5) | 0.0280 (15) | |
H241 | 0.2049 | 0.4246 | −0.2989 | 0.042* | |
H242 | 0.3276 | 0.3873 | −0.2454 | 0.042* | |
H243 | 0.2343 | 0.4268 | −0.1893 | 0.042* | |
C25 | −0.0026 (6) | 0.3706 (3) | −0.2302 (5) | 0.0294 (15) | |
H251 | −0.0379 | 0.3929 | −0.2854 | 0.044* | |
H252 | −0.0002 | 0.3962 | −0.1763 | 0.044* | |
H253 | −0.0615 | 0.3366 | −0.2238 | 0.044* | |
C26 | 0.3913 (5) | 0.1791 (2) | 0.2281 (5) | 0.0192 (13) | |
C27 | 0.4653 (5) | 0.2236 (2) | 0.2979 (4) | 0.0177 (12) | |
H27 | 0.5388 | 0.2435 | 0.2694 | 0.021* | |
C28 | 0.5307 (6) | 0.1893 (3) | 0.3853 (5) | 0.0239 (14) | |
C29 | 0.4907 (6) | 0.1324 (3) | 0.2038 (5) | 0.0317 (17) | |
H291 | 0.5199 | 0.1078 | 0.2577 | 0.048* | |
H292 | 0.5697 | 0.1518 | 0.1841 | 0.048* | |
H293 | 0.4462 | 0.1075 | 0.1539 | 0.048* | |
C30 | 0.2674 (6) | 0.1514 (3) | 0.2616 (5) | 0.0263 (14) | |
H301 | 0.2274 | 0.1220 | 0.2171 | 0.039* | |
H302 | 0.2004 | 0.1823 | 0.2683 | 0.039* | |
H303 | 0.2947 | 0.1323 | 0.3210 | 0.039* | |
C31 | 0.4218 (6) | 0.3162 (2) | 0.3772 (5) | 0.0241 (14) | |
O15 | 0.2234 (4) | 0.2158 (2) | 0.4939 (4) | 0.0303 (11) | |
H15A | 0.160 (4) | 0.237 (3) | 0.470 (5) | 0.036* | |
H15B | 0.274 (4) | 0.201 (3) | 0.457 (4) | 0.036* | |
O16 | −0.3389 (5) | 0.3867 (2) | 0.6008 (4) | 0.0437 (14) | |
H16A | −0.426 (4) | 0.384 (3) | 0.589 (5) | 0.052* | |
H16B | −0.320 (7) | 0.404 (3) | 0.656 (3) | 0.052* | |
O17 | −0.2663 (4) | 0.1395 (2) | 0.5663 (4) | 0.0371 (13) | |
H17A | −0.332 (6) | 0.130 (3) | 0.612 (4) | 0.045* | |
H17B | −0.309 (6) | 0.161 (3) | 0.528 (4) | 0.045* | |
O18 | −0.1341 (5) | 0.0193 (2) | 0.5689 (4) | 0.0419 (14) | |
H18A | −0.099 (6) | −0.012 (2) | 0.551 (3) | 0.050* | |
H18B | −0.215 (5) | 0.017 (3) | 0.529 (4) | 0.050* | |
O19 | −0.1714 (6) | 0.5307 (3) | 0.5386 (5) | 0.0511 (16) | |
H19A | −0.178 (8) | 0.558 (3) | 0.492 (3) | 0.061* | |
H19B | −0.263 (5) | 0.538 (4) | 0.546 (6) | 0.061* | |
O20 | 0.3770 (5) | 0.3948 (2) | 0.5582 (4) | 0.0324 (11) | |
H20A | 0.358 (8) | 0.389 (3) | 0.505 (3) | 0.039* | |
H20B | 0.378 (7) | 0.4308 (19) | 0.575 (5) | 0.039* | |
O21 | 0.4477 (5) | 0.0584 (2) | 0.4806 (4) | 0.0404 (13) | |
H21A | 0.500 (6) | 0.043 (3) | 0.536 (3) | 0.049* | |
H21B | 0.471 (7) | 0.0929 (17) | 0.473 (5) | 0.049* | |
O22 | 0.0158 (5) | 0.4403 (2) | 0.5401 (4) | 0.0472 (15) | |
H22A | −0.015 (7) | 0.4070 (19) | 0.532 (7) | 0.057* | |
H22B | −0.034 (6) | 0.468 (2) | 0.551 (5) | 0.057* | |
O23 | 0.3394 (7) | 0.5114 (3) | 0.5963 (6) | 0.071 (2) | |
H23A | 0.309 (7) | 0.535 (3) | 0.640 (5) | 0.085* | |
H23B | 0.411 (6) | 0.528 (3) | 0.587 (5) | 0.085* | |
O24 | −0.1603 (6) | 0.0921 (2) | 0.3433 (5) | 0.0582 (18) | |
H24 | −0.194 (6) | 0.121 (2) | 0.367 (7) | 0.070* | |
C32 | −0.0777 (11) | 0.0784 (5) | 0.2737 (10) | 0.023 (3) | 0.50 |
H321 | −0.0302 | 0.0405 | 0.2894 | 0.028* | 0.50 |
H322 | −0.0080 | 0.1095 | 0.2732 | 0.028* | 0.50 |
C33 | −0.1537 (13) | 0.0736 (5) | 0.1831 (11) | 0.032 (4) | 0.50 |
H331 | −0.2232 | 0.0430 | 0.1831 | 0.048* | 0.50 |
H332 | −0.0924 | 0.0632 | 0.1391 | 0.048* | 0.50 |
H333 | −0.1973 | 0.1116 | 0.1658 | 0.048* | 0.50 |
O25 | −0.3299 (7) | 0.3969 (3) | 0.7911 (5) | 0.074 (2) | |
H25 | −0.379 (9) | 0.366 (3) | 0.807 (6) | 0.088* | |
C34 | −0.3417 (14) | 0.4432 (6) | 0.8523 (12) | 0.037 (3)* | 0.50 |
H341 | −0.4367 | 0.4571 | 0.8455 | 0.045* | 0.50 |
H342 | −0.3164 | 0.4291 | 0.9161 | 0.045* | 0.50 |
C35 | −0.2616 (13) | 0.4869 (6) | 0.8356 (12) | 0.036 (3)* | 0.50 |
H351 | −0.1920 | 0.4929 | 0.8888 | 0.054* | 0.50 |
H352 | −0.3151 | 0.5231 | 0.8239 | 0.054* | 0.50 |
H353 | −0.2180 | 0.4774 | 0.7817 | 0.054* | 0.50 |
U11 | U22 | U33 | U12 | U13 | U23 | |
Au1 | 0.01639 (9) | 0.01930 (10) | 0.01535 (13) | −0.00107 (8) | 0.00128 (9) | −0.00084 (9) |
Au2 | 0.01962 (10) | 0.02284 (11) | 0.01628 (13) | 0.00276 (8) | −0.00192 (9) | −0.00434 (10) |
Au3 | 0.02377 (11) | 0.02188 (11) | 0.01550 (13) | −0.00496 (9) | 0.00572 (9) | −0.00290 (10) |
Au4 | 0.01765 (9) | 0.01778 (10) | 0.01554 (13) | 0.00093 (7) | 0.00264 (9) | −0.00101 (9) |
Ni1 | 0.0127 (3) | 0.0176 (4) | 0.0139 (4) | 0.0003 (2) | 0.0015 (3) | −0.0021 (3) |
Ni2 | 0.0147 (3) | 0.0143 (3) | 0.0145 (4) | −0.0017 (3) | 0.0020 (3) | −0.0007 (3) |
K1 | 0.0215 (6) | 0.0323 (7) | 0.0233 (8) | 0.0025 (5) | 0.0028 (6) | 0.0057 (6) |
K2 | 0.0237 (6) | 0.0222 (6) | 0.0320 (9) | 0.0001 (5) | 0.0043 (6) | 0.0033 (6) |
K3 | 0.0329 (7) | 0.0316 (8) | 0.0437 (11) | 0.0022 (6) | 0.0048 (7) | 0.0122 (7) |
K4 | 0.0184 (6) | 0.0251 (7) | 0.0417 (10) | −0.0012 (5) | −0.0024 (6) | 0.0034 (6) |
S1 | 0.0167 (6) | 0.0211 (7) | 0.0141 (8) | 0.0017 (5) | 0.0027 (6) | 0.0003 (6) |
S2 | 0.0171 (6) | 0.0202 (7) | 0.0172 (8) | 0.0015 (5) | 0.0013 (6) | −0.0033 (6) |
S3 | 0.0206 (6) | 0.0180 (7) | 0.0157 (8) | −0.0034 (5) | 0.0043 (6) | −0.0006 (6) |
S4 | 0.0165 (6) | 0.0168 (6) | 0.0133 (8) | −0.0008 (5) | 0.0024 (6) | −0.0006 (6) |
S5 | 0.0202 (7) | 0.0210 (7) | 0.0179 (9) | −0.0014 (5) | 0.0040 (6) | −0.0006 (6) |
S6 | 0.0180 (6) | 0.0232 (7) | 0.0175 (8) | 0.0015 (5) | 0.0023 (6) | −0.0034 (6) |
O1 | 0.027 (2) | 0.022 (2) | 0.030 (3) | −0.0033 (17) | −0.006 (2) | 0.000 (2) |
O2 | 0.024 (2) | 0.057 (3) | 0.030 (3) | 0.019 (2) | −0.008 (2) | −0.004 (3) |
O3 | 0.023 (2) | 0.021 (2) | 0.015 (2) | −0.0017 (15) | 0.0052 (18) | −0.0008 (17) |
O4 | 0.029 (2) | 0.017 (2) | 0.032 (3) | 0.0057 (16) | 0.011 (2) | −0.006 (2) |
O5 | 0.033 (2) | 0.028 (2) | 0.043 (4) | −0.0024 (19) | −0.008 (2) | 0.004 (2) |
O6 | 0.030 (2) | 0.016 (2) | 0.068 (4) | −0.0077 (18) | −0.019 (3) | 0.003 (2) |
O7 | 0.026 (2) | 0.028 (2) | 0.022 (3) | 0.0030 (17) | 0.0120 (19) | 0.000 (2) |
O8 | 0.031 (2) | 0.027 (2) | 0.026 (3) | 0.0056 (18) | 0.006 (2) | 0.013 (2) |
O9 | 0.029 (2) | 0.017 (2) | 0.036 (3) | 0.0019 (16) | 0.015 (2) | 0.003 (2) |
O10 | 0.0157 (18) | 0.046 (3) | 0.027 (3) | −0.0108 (19) | −0.0018 (19) | 0.010 (2) |
O11 | 0.032 (2) | 0.032 (2) | 0.027 (3) | 0.0059 (18) | 0.004 (2) | 0.006 (2) |
O12 | 0.026 (2) | 0.050 (3) | 0.020 (3) | 0.017 (2) | 0.003 (2) | 0.006 (2) |
O13 | 0.019 (2) | 0.025 (2) | 0.031 (3) | −0.0026 (16) | −0.007 (2) | −0.007 (2) |
O14 | 0.028 (2) | 0.025 (2) | 0.024 (3) | 0.0075 (17) | −0.009 (2) | −0.0058 (19) |
N1 | 0.018 (2) | 0.025 (2) | 0.012 (3) | −0.0007 (19) | −0.003 (2) | −0.009 (2) |
N2 | 0.011 (2) | 0.023 (2) | 0.018 (3) | −0.0015 (17) | −0.001 (2) | −0.002 (2) |
N3 | 0.015 (2) | 0.019 (2) | 0.017 (3) | 0.0019 (17) | −0.003 (2) | −0.003 (2) |
N4 | 0.017 (2) | 0.021 (2) | 0.018 (3) | −0.0056 (18) | 0.001 (2) | 0.000 (2) |
N5 | 0.018 (2) | 0.024 (2) | 0.013 (3) | 0.0012 (18) | 0.002 (2) | 0.001 (2) |
N6 | 0.015 (2) | 0.022 (2) | 0.027 (3) | 0.0044 (18) | −0.005 (2) | −0.011 (2) |
C1 | 0.011 (2) | 0.025 (3) | 0.020 (4) | 0.001 (2) | 0.001 (2) | −0.001 (3) |
C2 | 0.015 (2) | 0.019 (3) | 0.011 (3) | 0.0003 (19) | 0.001 (2) | 0.002 (2) |
C3 | 0.013 (2) | 0.023 (3) | 0.031 (4) | −0.007 (2) | 0.001 (3) | 0.002 (3) |
C4 | 0.015 (3) | 0.026 (3) | 0.043 (5) | −0.003 (2) | 0.008 (3) | −0.003 (3) |
C5 | 0.032 (3) | 0.026 (3) | 0.018 (4) | 0.011 (3) | −0.005 (3) | −0.005 (3) |
C6 | 0.019 (3) | 0.022 (3) | 0.015 (3) | 0.000 (2) | 0.002 (2) | −0.005 (2) |
C7 | 0.018 (3) | 0.019 (3) | 0.009 (3) | 0.001 (2) | 0.006 (2) | −0.001 (2) |
C8 | 0.014 (2) | 0.026 (3) | 0.011 (3) | −0.001 (2) | 0.004 (2) | −0.002 (2) |
C9 | 0.018 (3) | 0.036 (4) | 0.019 (4) | −0.001 (2) | 0.000 (3) | 0.000 (3) |
C10 | 0.028 (3) | 0.028 (3) | 0.030 (4) | 0.008 (3) | 0.000 (3) | 0.003 (3) |
C11 | 0.016 (2) | 0.021 (3) | 0.016 (3) | −0.004 (2) | 0.002 (2) | 0.002 (2) |
C12 | 0.020 (3) | 0.012 (2) | 0.019 (3) | −0.002 (2) | 0.002 (2) | 0.004 (2) |
C13 | 0.020 (3) | 0.016 (3) | 0.033 (4) | −0.001 (2) | 0.005 (3) | −0.004 (3) |
C14 | 0.019 (3) | 0.021 (3) | 0.041 (5) | 0.003 (2) | 0.006 (3) | −0.007 (3) |
C15 | 0.023 (3) | 0.039 (4) | 0.041 (5) | −0.008 (3) | 0.008 (3) | 0.006 (3) |
C16 | 0.017 (3) | 0.017 (3) | 0.025 (4) | −0.004 (2) | 0.006 (3) | 0.001 (3) |
C17 | 0.016 (2) | 0.014 (3) | 0.021 (3) | 0.0002 (19) | 0.008 (2) | 0.005 (2) |
C18 | 0.013 (2) | 0.024 (3) | 0.014 (3) | −0.003 (2) | 0.000 (2) | 0.001 (2) |
C19 | 0.020 (3) | 0.028 (3) | 0.025 (4) | 0.000 (2) | 0.003 (3) | −0.002 (3) |
C20 | 0.029 (3) | 0.014 (3) | 0.031 (4) | −0.008 (2) | 0.006 (3) | −0.002 (3) |
C21 | 0.021 (3) | 0.013 (2) | 0.026 (4) | 0.000 (2) | 0.007 (3) | −0.001 (2) |
C22 | 0.017 (3) | 0.021 (3) | 0.010 (3) | 0.000 (2) | 0.009 (2) | 0.001 (2) |
C23 | 0.021 (3) | 0.028 (3) | 0.017 (3) | −0.009 (2) | 0.006 (3) | 0.003 (3) |
C24 | 0.036 (3) | 0.028 (3) | 0.021 (4) | −0.004 (3) | 0.008 (3) | −0.002 (3) |
C25 | 0.025 (3) | 0.038 (4) | 0.025 (4) | 0.014 (3) | 0.004 (3) | 0.007 (3) |
C26 | 0.019 (3) | 0.019 (3) | 0.019 (4) | 0.004 (2) | −0.001 (3) | −0.002 (2) |
C27 | 0.020 (3) | 0.020 (3) | 0.013 (3) | 0.003 (2) | 0.002 (2) | 0.000 (2) |
C28 | 0.021 (3) | 0.028 (3) | 0.022 (4) | 0.006 (2) | −0.002 (3) | −0.002 (3) |
C29 | 0.029 (3) | 0.029 (3) | 0.033 (5) | 0.008 (3) | −0.008 (3) | −0.007 (3) |
C30 | 0.035 (3) | 0.021 (3) | 0.023 (4) | −0.007 (2) | 0.003 (3) | −0.001 (3) |
C31 | 0.030 (3) | 0.015 (3) | 0.027 (4) | 0.000 (2) | 0.004 (3) | 0.004 (3) |
O15 | 0.028 (2) | 0.044 (3) | 0.020 (3) | 0.0066 (19) | 0.005 (2) | 0.005 (2) |
O16 | 0.046 (3) | 0.053 (3) | 0.029 (3) | 0.003 (3) | −0.004 (3) | −0.005 (3) |
O17 | 0.029 (2) | 0.050 (3) | 0.031 (3) | 0.002 (2) | 0.001 (2) | 0.008 (3) |
O18 | 0.037 (3) | 0.046 (3) | 0.041 (4) | 0.002 (2) | 0.001 (3) | 0.013 (3) |
O19 | 0.046 (3) | 0.071 (4) | 0.039 (4) | 0.017 (3) | 0.020 (3) | 0.014 (3) |
O20 | 0.051 (3) | 0.027 (2) | 0.023 (3) | 0.002 (2) | 0.016 (3) | 0.001 (2) |
O21 | 0.040 (3) | 0.044 (3) | 0.036 (4) | −0.006 (2) | 0.001 (3) | 0.004 (3) |
O22 | 0.053 (3) | 0.041 (3) | 0.043 (4) | 0.007 (3) | −0.008 (3) | −0.005 (3) |
O23 | 0.079 (4) | 0.044 (4) | 0.101 (7) | −0.020 (3) | 0.049 (5) | −0.025 (4) |
O24 | 0.061 (4) | 0.035 (3) | 0.078 (6) | 0.007 (3) | 0.010 (4) | 0.000 (3) |
C32 | 0.015 (5) | 0.025 (6) | 0.034 (9) | 0.001 (4) | 0.017 (5) | 0.010 (6) |
C33 | 0.037 (7) | 0.014 (6) | 0.047 (11) | 0.010 (5) | 0.011 (7) | 0.008 (6) |
O25 | 0.088 (5) | 0.088 (5) | 0.047 (5) | −0.015 (4) | 0.019 (4) | 0.001 (4) |
Au1—S5 | 2.3235 (15) | N6—C31 | 1.383 (8) |
Au1—S1 | 2.3390 (15) | N6—C27 | 1.445 (7) |
Au1—Ni1 | 2.8686 (8) | N6—H6 | 0.8800 |
Au1—Au2 | 3.0635 (5) | C1—C5 | 1.497 (8) |
Au1—Au4 | 3.1730 (6) | C1—C2 | 1.520 (9) |
Au1—Au3 | 3.1783 (5) | C1—C4 | 1.523 (8) |
Au2—S2 | 2.3030 (14) | C2—C3 | 1.540 (7) |
Au2—S6 | 2.3122 (15) | C2—H2 | 1.0000 |
Au2—Au4 | 3.1764 (5) | C4—H41 | 0.9800 |
Au3—S3 | 2.2837 (16) | C4—H42 | 0.9800 |
Au3—S5 | 2.3017 (17) | C4—H43 | 0.9800 |
Au3—Au4 | 3.0542 (5) | C5—H51 | 0.9800 |
Au4—S4 | 2.3118 (14) | C5—H52 | 0.9800 |
Au4—S6 | 2.3134 (14) | C5—H53 | 0.9800 |
Au4—Ni2 | 3.1545 (9) | C6—C10 | 1.518 (8) |
Ni1—N1 | 1.927 (5) | C6—C9 | 1.525 (8) |
Ni1—N2 | 1.940 (5) | C6—C7 | 1.553 (8) |
Ni1—S1 | 2.1627 (18) | C7—C8 | 1.553 (8) |
Ni1—S2 | 2.1664 (16) | C7—H7 | 1.0000 |
Ni2—N4 | 1.901 (5) | C9—H91 | 0.9800 |
Ni2—N3 | 1.930 (4) | C9—H92 | 0.9800 |
Ni2—S3 | 2.1634 (18) | C9—H93 | 0.9800 |
Ni2—S4 | 2.1792 (15) | C10—H101 | 0.9800 |
K1—O13i | 2.651 (4) | C10—H102 | 0.9800 |
K1—O10ii | 2.706 (4) | C10—H103 | 0.9800 |
K1—O7 | 2.761 (5) | C11—C15 | 1.487 (9) |
K1—O16 | 2.807 (6) | C11—C14 | 1.541 (8) |
K1—O1ii | 2.909 (5) | C11—C12 | 1.560 (9) |
K1—O8 | 2.990 (5) | C12—C13 | 1.542 (8) |
K1—O17 | 3.035 (5) | C12—H12 | 1.0000 |
K1—O12i | 3.192 (5) | C14—H141 | 0.9800 |
K1—K2 | 3.855 (2) | C14—H142 | 0.9800 |
K1—K3 | 4.069 (2) | C14—H143 | 0.9800 |
K1—K4iii | 4.902 (2) | C15—H151 | 0.9800 |
K2—O5i | 2.705 (5) | C15—H152 | 0.9800 |
K2—O16 | 2.732 (6) | C15—H153 | 0.9800 |
K2—O13i | 2.738 (4) | C16—C20 | 1.524 (7) |
K2—O4iv | 2.768 (5) | C16—C19 | 1.524 (8) |
K2—O7 | 2.802 (4) | C16—C17 | 1.530 (8) |
K2—O19 | 3.224 (7) | C17—C18 | 1.555 (9) |
K3—O8 | 2.725 (4) | C17—H17 | 1.0000 |
K3—O17 | 2.733 (5) | C19—H191 | 0.9800 |
K3—O3ii | 2.772 (4) | C19—H192 | 0.9800 |
K3—O24 | 2.918 (7) | C19—H193 | 0.9800 |
K3—O15 | 2.975 (5) | C20—H201 | 0.9800 |
K3—O18 | 3.131 (5) | C20—H202 | 0.9800 |
K3—O9ii | 3.132 (5) | C20—H203 | 0.9800 |
K3—O19v | 3.238 (7) | C21—C25 | 1.523 (8) |
K3—K4ii | 3.887 (2) | C21—C24 | 1.533 (8) |
K4—O1vi | 2.629 (4) | C21—C22 | 1.538 (9) |
K4—O3 | 2.655 (4) | C22—C23 | 1.535 (8) |
K4—O6vii | 2.741 (4) | C22—H22 | 1.0000 |
K4—O15viii | 2.751 (5) | C24—H241 | 0.9800 |
K4—O9 | 2.759 (4) | C24—H242 | 0.9800 |
K4—O11viii | 3.105 (6) | C24—H243 | 0.9800 |
K4—O21viii | 3.213 (6) | C25—H251 | 0.9800 |
K4—K3viii | 3.887 (2) | C25—H252 | 0.9800 |
K4—K1ix | 4.902 (2) | C25—H253 | 0.9800 |
S1—C1 | 1.867 (5) | C26—C29 | 1.524 (8) |
S2—C6 | 1.856 (6) | C26—C30 | 1.527 (8) |
S3—C11 | 1.867 (5) | C26—C27 | 1.551 (8) |
S4—C16 | 1.862 (7) | C27—C28 | 1.565 (9) |
S5—C21 | 1.863 (6) | C27—H27 | 1.0000 |
S6—C26 | 1.874 (7) | C29—H291 | 0.9800 |
O1—C3 | 1.243 (8) | C29—H292 | 0.9800 |
O1—K4i | 2.629 (4) | C29—H293 | 0.9800 |
O1—K1viii | 2.909 (5) | C30—H301 | 0.9800 |
O2—C3 | 1.248 (8) | C30—H302 | 0.9800 |
O3—C8 | 1.261 (7) | C30—H303 | 0.9800 |
O3—K3viii | 2.772 (4) | O15—K4ii | 2.751 (5) |
O4—C8 | 1.237 (7) | O15—H15A | 0.83 (3) |
O4—K2x | 2.768 (5) | O15—H15B | 0.86 (4) |
O5—C13 | 1.246 (8) | O16—H16A | 0.86 (4) |
O5—K2vi | 2.705 (5) | O16—H16B | 0.89 (4) |
O6—C13 | 1.227 (7) | O17—H17A | 1.02 (3) |
O6—K4xi | 2.741 (4) | O17—H17B | 0.82 (4) |
O7—C18 | 1.252 (7) | O18—H18A | 0.86 (3) |
O8—C18 | 1.236 (7) | O18—H18B | 0.93 (3) |
O9—C23 | 1.252 (7) | O19—K3xii | 3.238 (7) |
O9—K3viii | 3.132 (5) | O19—H19A | 0.92 (4) |
O10—C23 | 1.251 (6) | O19—H19B | 0.95 (4) |
O10—K1viii | 2.706 (4) | O20—H20A | 0.80 (4) |
O11—C28 | 1.249 (8) | O20—H20B | 0.85 (4) |
O11—K4ii | 3.105 (6) | O21—K4ii | 3.213 (6) |
O12—C28 | 1.262 (7) | O21—H21A | 0.97 (3) |
O12—K1vi | 3.192 (5) | O21—H21B | 0.83 (3) |
O13—C31 | 1.227 (7) | O22—H22A | 0.82 (4) |
O13—K1vi | 2.651 (4) | O22—H22B | 0.83 (3) |
O13—K2vi | 2.738 (4) | O23—H23A | 0.92 (4) |
O14—C31 | 1.273 (7) | O23—H23B | 0.83 (4) |
N1—C2 | 1.494 (7) | O24—C32 | 1.435 (14) |
N1—H1A | 0.9200 | O24—H24 | 0.83 (4) |
N1—H1B | 0.9200 | C32—C33 | 1.44 (2) |
N2—C7 | 1.493 (7) | C32—H321 | 0.9900 |
N2—H2A | 0.9200 | C32—H322 | 0.9900 |
N2—H2B | 0.9200 | C33—H331 | 0.9800 |
N3—C12 | 1.455 (7) | C33—H332 | 0.9800 |
N3—H3A | 0.9200 | C33—H333 | 0.9800 |
N3—H3B | 0.9200 | O25—C34 | 1.398 (16) |
N4—C17 | 1.480 (7) | O25—H25 | 0.90 (4) |
N4—H4A | 0.9200 | C34—C35 | 1.317 (19) |
N4—H4B | 0.9200 | C34—H341 | 0.9900 |
N5—C22 | 1.496 (7) | C34—H342 | 0.9900 |
N5—H5A | 0.9100 | C35—H351 | 0.9800 |
N5—H5B | 0.9100 | C35—H352 | 0.9800 |
N5—H5C | 0.9100 | C35—H353 | 0.9800 |
S5—Au1—S1 | 175.40 (6) | K4—O9—K3viii | 82.30 (13) |
S5—Au1—Ni1 | 127.70 (4) | C23—O10—K1viii | 140.1 (4) |
S1—Au1—Ni1 | 47.75 (4) | C28—O11—K4ii | 164.7 (4) |
S5—Au1—Au2 | 99.12 (4) | C28—O12—K1vi | 87.1 (4) |
S1—Au1—Au2 | 79.19 (4) | C31—O13—K1vi | 144.6 (4) |
Ni1—Au1—Au2 | 73.708 (19) | C31—O13—K2vi | 116.9 (4) |
S5—Au1—Au4 | 92.55 (4) | K1vi—O13—K2vi | 91.33 (12) |
S1—Au1—Au4 | 90.37 (4) | C2—N1—Ni1 | 118.5 (4) |
Ni1—Au1—Au4 | 123.844 (18) | C2—N1—H1A | 107.7 |
Au2—Au1—Au4 | 61.209 (11) | Ni1—N1—H1A | 107.7 |
S5—Au1—Au3 | 46.31 (4) | C2—N1—H1B | 107.7 |
S1—Au1—Au3 | 138.17 (4) | Ni1—N1—H1B | 107.7 |
Ni1—Au1—Au3 | 173.213 (17) | H1A—N1—H1B | 107.1 |
Au2—Au1—Au3 | 103.046 (15) | C7—N2—Ni1 | 116.2 (4) |
Au4—Au1—Au3 | 57.486 (8) | C7—N2—H2A | 108.2 |
S2—Au2—S6 | 177.61 (6) | Ni1—N2—H2A | 108.2 |
S2—Au2—Au1 | 86.48 (4) | C7—N2—H2B | 108.2 |
S6—Au2—Au1 | 95.78 (4) | Ni1—N2—H2B | 108.2 |
S2—Au2—Au4 | 134.51 (4) | H2A—N2—H2B | 107.4 |
S6—Au2—Au4 | 46.65 (4) | C12—N3—Ni2 | 118.3 (4) |
Au1—Au2—Au4 | 61.095 (13) | C12—N3—H3A | 107.7 |
S3—Au3—S5 | 173.69 (5) | Ni2—N3—H3A | 107.7 |
S3—Au3—Au4 | 87.30 (4) | C12—N3—H3B | 107.7 |
S5—Au3—Au4 | 96.11 (4) | Ni2—N3—H3B | 107.7 |
S3—Au3—Au1 | 131.96 (4) | H3A—N3—H3B | 107.1 |
S5—Au3—Au1 | 46.88 (4) | C17—N4—Ni2 | 115.5 (4) |
Au4—Au3—Au1 | 61.169 (13) | C17—N4—H4A | 108.4 |
S4—Au4—S6 | 177.97 (6) | Ni2—N4—H4A | 108.4 |
S4—Au4—Au3 | 81.37 (4) | C17—N4—H4B | 108.4 |
S6—Au4—Au3 | 99.02 (4) | Ni2—N4—H4B | 108.4 |
S4—Au4—Ni2 | 43.69 (4) | H4A—N4—H4B | 107.5 |
S6—Au4—Ni2 | 134.50 (4) | C22—N5—H5A | 109.5 |
Au3—Au4—Ni2 | 73.00 (2) | C22—N5—H5B | 109.5 |
S4—Au4—Au1 | 89.05 (4) | H5A—N5—H5B | 109.5 |
S6—Au4—Au1 | 92.88 (4) | C22—N5—H5C | 109.5 |
Au3—Au4—Au1 | 61.344 (12) | H5A—N5—H5C | 109.5 |
Ni2—Au4—Au1 | 118.742 (16) | H5B—N5—H5C | 109.5 |
S4—Au4—Au2 | 135.28 (3) | C31—N6—C27 | 121.5 (4) |
S6—Au4—Au2 | 46.61 (4) | C31—N6—H6 | 119.2 |
Au3—Au4—Au2 | 103.302 (16) | C27—N6—H6 | 119.2 |
Ni2—Au4—Au2 | 176.101 (18) | C5—C1—C2 | 112.1 (5) |
Au1—Au4—Au2 | 57.696 (8) | C5—C1—C4 | 110.4 (5) |
N1—Ni1—N2 | 92.0 (2) | C2—C1—C4 | 112.1 (5) |
N1—Ni1—S1 | 87.60 (16) | C5—C1—S1 | 107.9 (4) |
N2—Ni1—S1 | 172.03 (15) | C2—C1—S1 | 106.1 (4) |
N1—Ni1—S2 | 173.77 (15) | C4—C1—S1 | 108.0 (4) |
N2—Ni1—S2 | 87.45 (14) | N1—C2—C1 | 109.5 (5) |
S1—Ni1—S2 | 93.75 (6) | N1—C2—C3 | 109.6 (5) |
N1—Ni1—Au1 | 91.53 (14) | C1—C2—C3 | 115.9 (5) |
N2—Ni1—Au1 | 118.89 (14) | N1—C2—H2 | 107.1 |
S1—Ni1—Au1 | 53.19 (4) | C1—C2—H2 | 107.1 |
S2—Ni1—Au1 | 94.15 (5) | C3—C2—H2 | 107.1 |
N4—Ni2—N3 | 90.1 (2) | O1—C3—O2 | 125.5 (5) |
N4—Ni2—S3 | 174.26 (16) | O1—C3—C2 | 118.3 (5) |
N3—Ni2—S3 | 86.66 (17) | O2—C3—C2 | 116.1 (6) |
N4—Ni2—S4 | 88.41 (14) | C1—C4—H41 | 109.5 |
N3—Ni2—S4 | 175.90 (14) | C1—C4—H42 | 109.5 |
S3—Ni2—S4 | 95.17 (6) | H41—C4—H42 | 109.5 |
N4—Ni2—Au4 | 98.85 (15) | C1—C4—H43 | 109.5 |
N3—Ni2—Au4 | 129.50 (14) | H41—C4—H43 | 109.5 |
S3—Ni2—Au4 | 86.87 (5) | H42—C4—H43 | 109.5 |
S4—Ni2—Au4 | 47.12 (4) | C1—C5—H51 | 109.5 |
O13i—K1—O10ii | 166.27 (14) | C1—C5—H52 | 109.5 |
O13i—K1—O7 | 78.11 (14) | H51—C5—H52 | 109.5 |
O10ii—K1—O7 | 89.29 (14) | C1—C5—H53 | 109.5 |
O13i—K1—O16 | 73.90 (14) | H51—C5—H53 | 109.5 |
O10ii—K1—O16 | 98.24 (16) | H52—C5—H53 | 109.5 |
O7—K1—O16 | 77.47 (16) | C10—C6—C9 | 111.5 (5) |
O13i—K1—O1ii | 103.60 (13) | C10—C6—C7 | 110.8 (5) |
O10ii—K1—O1ii | 87.23 (13) | C9—C6—C7 | 111.0 (5) |
O7—K1—O1ii | 165.38 (14) | C10—C6—S2 | 107.8 (5) |
O16—K1—O1ii | 88.98 (16) | C9—C6—S2 | 111.8 (4) |
O13i—K1—O8 | 100.80 (14) | C7—C6—S2 | 103.7 (4) |
O10ii—K1—O8 | 73.34 (14) | N2—C7—C6 | 109.3 (4) |
O7—K1—O8 | 45.36 (12) | N2—C7—C8 | 111.1 (5) |
O16—K1—O8 | 121.35 (15) | C6—C7—C8 | 112.4 (4) |
O1ii—K1—O8 | 145.46 (12) | N2—C7—H7 | 107.9 |
O13i—K1—O17 | 117.93 (14) | C6—C7—H7 | 107.9 |
O10ii—K1—O17 | 74.16 (14) | C8—C7—H7 | 107.9 |
O7—K1—O17 | 127.60 (14) | O4—C8—O3 | 127.6 (6) |
O16—K1—O17 | 152.69 (18) | O4—C8—C7 | 116.5 (5) |
O1ii—K1—O17 | 64.80 (14) | O3—C8—C7 | 116.0 (5) |
O8—K1—O17 | 82.27 (14) | C6—C9—H91 | 109.5 |
O13i—K1—O12i | 71.43 (12) | C6—C9—H92 | 109.5 |
O10ii—K1—O12i | 116.07 (14) | H91—C9—H92 | 109.5 |
O7—K1—O12i | 96.92 (14) | C6—C9—H93 | 109.5 |
O16—K1—O12i | 145.28 (14) | H91—C9—H93 | 109.5 |
O1ii—K1—O12i | 97.36 (13) | H92—C9—H93 | 109.5 |
O8—K1—O12i | 67.85 (12) | C6—C10—H101 | 109.5 |
O17—K1—O12i | 52.37 (14) | C6—C10—H102 | 109.5 |
O13i—K1—K2 | 45.24 (9) | H101—C10—H102 | 109.5 |
O10ii—K1—K2 | 121.42 (11) | C6—C10—H103 | 109.5 |
O7—K1—K2 | 46.57 (9) | H101—C10—H103 | 109.5 |
O16—K1—K2 | 45.09 (13) | H102—C10—H103 | 109.5 |
O1ii—K1—K2 | 125.13 (9) | C15—C11—C14 | 113.2 (5) |
O8—K1—K2 | 89.40 (9) | C15—C11—C12 | 111.4 (5) |
O17—K1—K2 | 159.41 (12) | C14—C11—C12 | 110.6 (5) |
O12i—K1—K2 | 107.05 (10) | C15—C11—S3 | 109.0 (4) |
O13i—K1—K3 | 125.47 (11) | C14—C11—S3 | 110.7 (4) |
O10ii—K1—K3 | 58.19 (12) | C12—C11—S3 | 101.2 (4) |
O7—K1—K3 | 86.68 (9) | N3—C12—C13 | 112.0 (5) |
O16—K1—K3 | 152.01 (12) | N3—C12—C11 | 108.5 (4) |
O1ii—K1—K3 | 103.43 (9) | C13—C12—C11 | 116.0 (5) |
O8—K1—K3 | 42.04 (9) | N3—C12—H12 | 106.6 |
O17—K1—K3 | 42.20 (10) | C13—C12—H12 | 106.6 |
O12i—K1—K3 | 58.80 (8) | C11—C12—H12 | 106.6 |
K2—K1—K3 | 131.33 (5) | O6—C13—O5 | 126.2 (6) |
O13i—K1—K4iii | 87.97 (10) | O6—C13—C12 | 117.4 (6) |
O10ii—K1—K4iii | 105.11 (10) | O5—C13—C12 | 116.2 (5) |
O7—K1—K4iii | 164.70 (11) | C11—C14—H141 | 109.5 |
O16—K1—K4iii | 104.92 (13) | C11—C14—H142 | 109.5 |
O1ii—K1—K4iii | 26.24 (9) | H141—C14—H142 | 109.5 |
O8—K1—K4iii | 133.60 (10) | C11—C14—H143 | 109.5 |
O17—K1—K4iii | 54.30 (10) | H141—C14—H143 | 109.5 |
O12i—K1—K4iii | 72.36 (9) | H142—C14—H143 | 109.5 |
K2—K1—K4iii | 125.08 (4) | C11—C15—H151 | 109.5 |
K3—K1—K4iii | 96.47 (4) | C11—C15—H152 | 109.5 |
O5i—K2—O16 | 118.52 (18) | H151—C15—H152 | 109.5 |
O5i—K2—O13i | 105.16 (13) | C11—C15—H153 | 109.5 |
O16—K2—O13i | 73.77 (16) | H151—C15—H153 | 109.5 |
O5i—K2—O4iv | 87.77 (15) | H152—C15—H153 | 109.5 |
O16—K2—O4iv | 139.86 (16) | C20—C16—C19 | 111.2 (5) |
O13i—K2—O4iv | 131.29 (15) | C20—C16—C17 | 111.4 (5) |
O5i—K2—O7 | 163.28 (18) | C19—C16—C17 | 112.8 (5) |
O16—K2—O7 | 78.03 (15) | C20—C16—S4 | 109.7 (5) |
O13i—K2—O7 | 76.00 (12) | C19—C16—S4 | 105.7 (4) |
O4iv—K2—O7 | 79.57 (13) | C17—C16—S4 | 105.7 (4) |
O5i—K2—O19 | 89.46 (14) | N4—C17—C16 | 109.9 (5) |
O16—K2—O19 | 79.57 (17) | N4—C17—C18 | 110.7 (5) |
O13i—K2—O19 | 153.24 (17) | C16—C17—C18 | 114.8 (4) |
O4iv—K2—O19 | 70.35 (15) | N4—C17—H17 | 107.0 |
O7—K2—O19 | 96.42 (14) | C16—C17—H17 | 107.0 |
O5i—K2—K1 | 143.97 (11) | C18—C17—H17 | 107.0 |
O16—K2—K1 | 46.69 (12) | O8—C18—O7 | 127.1 (6) |
O13i—K2—K1 | 43.43 (9) | O8—C18—C17 | 116.3 (5) |
O4iv—K2—K1 | 125.01 (10) | O7—C18—C17 | 116.5 (5) |
O7—K2—K1 | 45.70 (9) | C16—C19—H191 | 109.5 |
O19—K2—K1 | 113.82 (12) | C16—C19—H192 | 109.5 |
O8—K3—O17 | 93.14 (15) | H191—C19—H192 | 109.5 |
O8—K3—O3ii | 142.63 (13) | C16—C19—H193 | 109.5 |
O17—K3—O3ii | 109.39 (15) | H191—C19—H193 | 109.5 |
O8—K3—O24 | 89.43 (16) | H192—C19—H193 | 109.5 |
O17—K3—O24 | 82.89 (18) | C16—C20—H201 | 109.5 |
O3ii—K3—O24 | 121.83 (15) | C16—C20—H202 | 109.5 |
O8—K3—O15 | 58.45 (12) | H201—C20—H202 | 109.5 |
O17—K3—O15 | 143.45 (16) | C16—C20—H203 | 109.5 |
O3ii—K3—O15 | 87.49 (13) | H201—C20—H203 | 109.5 |
O24—K3—O15 | 116.18 (18) | H202—C20—H203 | 109.5 |
O8—K3—O18 | 151.33 (13) | C25—C21—C24 | 110.2 (5) |
O17—K3—O18 | 61.59 (15) | C25—C21—C22 | 108.9 (5) |
O3ii—K3—O18 | 64.32 (12) | C24—C21—C22 | 110.2 (5) |
O24—K3—O18 | 74.99 (18) | C25—C21—S5 | 111.3 (5) |
O15—K3—O18 | 150.18 (13) | C24—C21—S5 | 106.7 (4) |
O8—K3—O9ii | 83.87 (13) | C22—C21—S5 | 109.5 (4) |
O17—K3—O9ii | 97.67 (16) | N5—C22—C23 | 109.0 (4) |
O3ii—K3—O9ii | 64.34 (12) | N5—C22—C21 | 112.0 (4) |
O24—K3—O9ii | 173.30 (16) | C23—C22—C21 | 116.0 (5) |
O15—K3—O9ii | 59.82 (13) | N5—C22—H22 | 106.4 |
O18—K3—O9ii | 111.19 (15) | C23—C22—H22 | 106.4 |
O8—K3—O19v | 130.32 (17) | C21—C22—H22 | 106.4 |
O17—K3—O19v | 130.11 (16) | O10—C23—O9 | 125.9 (5) |
O3ii—K3—O19v | 52.64 (15) | O10—C23—C22 | 116.2 (5) |
O24—K3—O19v | 75.56 (16) | O9—C23—C22 | 117.8 (4) |
O15—K3—O19v | 86.07 (14) | C21—C24—H241 | 109.5 |
O18—K3—O19v | 69.49 (15) | C21—C24—H242 | 109.5 |
O9ii—K3—O19v | 108.69 (13) | H241—C24—H242 | 109.5 |
O8—K3—K4ii | 100.45 (10) | C21—C24—H243 | 109.5 |
O17—K3—K4ii | 137.06 (14) | H241—C24—H243 | 109.5 |
O3ii—K3—K4ii | 43.08 (8) | H242—C24—H243 | 109.5 |
O24—K3—K4ii | 137.17 (13) | C21—C25—H251 | 109.5 |
O15—K3—K4ii | 44.87 (9) | C21—C25—H252 | 109.5 |
O18—K3—K4ii | 107.36 (10) | H251—C25—H252 | 109.5 |
O9ii—K3—K4ii | 44.70 (8) | C21—C25—H253 | 109.5 |
O19v—K3—K4ii | 66.28 (10) | H251—C25—H253 | 109.5 |
O8—K3—K1 | 47.29 (10) | H252—C25—H253 | 109.5 |
O17—K3—K1 | 48.25 (11) | C29—C26—C30 | 111.9 (5) |
O3ii—K3—K1 | 134.74 (11) | C29—C26—C27 | 110.0 (4) |
O24—K3—K1 | 96.54 (12) | C30—C26—C27 | 112.5 (6) |
O15—K3—K1 | 96.74 (10) | C29—C26—S6 | 103.7 (5) |
O18—K3—K1 | 109.81 (11) | C30—C26—S6 | 112.0 (4) |
O9ii—K3—K1 | 79.08 (8) | C27—C26—S6 | 106.3 (4) |
O19v—K3—K1 | 172.04 (12) | N6—C27—C26 | 112.0 (4) |
K4ii—K3—K1 | 120.74 (5) | N6—C27—C28 | 109.1 (5) |
O1vi—K4—O3 | 166.03 (17) | C26—C27—C28 | 109.2 (5) |
O1vi—K4—O6vii | 73.72 (13) | N6—C27—H27 | 108.9 |
O3—K4—O6vii | 101.49 (14) | C26—C27—H27 | 108.9 |
O1vi—K4—O15viii | 94.13 (14) | C28—C27—H27 | 108.9 |
O3—K4—O15viii | 94.67 (14) | O11—C28—O12 | 124.4 (6) |
O6vii—K4—O15viii | 156.39 (18) | O11—C28—C27 | 119.0 (5) |
O1vi—K4—O9 | 102.32 (14) | O12—C28—C27 | 116.6 (6) |
O3—K4—O9 | 71.34 (12) | C26—C29—H291 | 109.5 |
O6vii—K4—O9 | 134.46 (18) | C26—C29—H292 | 109.5 |
O15viii—K4—O9 | 67.18 (15) | H291—C29—H292 | 109.5 |
O1vi—K4—O11viii | 74.75 (15) | C26—C29—H293 | 109.5 |
O3—K4—O11viii | 119.21 (14) | H291—C29—H293 | 109.5 |
O6vii—K4—O11viii | 102.50 (16) | H292—C29—H293 | 109.5 |
O15viii—K4—O11viii | 54.20 (13) | C26—C30—H301 | 109.5 |
O9—K4—O11viii | 120.53 (14) | C26—C30—H302 | 109.5 |
O1vi—K4—O21viii | 108.27 (15) | H301—C30—H302 | 109.5 |
O3—K4—O21viii | 82.58 (13) | C26—C30—H303 | 109.5 |
O6vii—K4—O21viii | 75.44 (15) | H301—C30—H303 | 109.5 |
O15viii—K4—O21viii | 89.89 (15) | H302—C30—H303 | 109.5 |
O9—K4—O21viii | 142.93 (13) | O13—C31—O14 | 126.1 (6) |
O11viii—K4—O21viii | 51.82 (13) | O13—C31—N6 | 118.4 (5) |
O1vi—K4—K3viii | 140.26 (10) | O14—C31—N6 | 115.5 (5) |
O3—K4—K3viii | 45.47 (9) | K4ii—O15—K3 | 85.41 (14) |
O6vii—K4—K3viii | 146.01 (10) | K4ii—O15—H15A | 155 (5) |
O15viii—K4—K3viii | 49.72 (10) | K3—O15—H15A | 79 (4) |
O9—K4—K3viii | 53.00 (10) | K4ii—O15—H15B | 89 (4) |
O11viii—K4—K3viii | 91.34 (9) | K3—O15—H15B | 112 (5) |
O21viii—K4—K3viii | 89.93 (9) | H15A—O15—H15B | 116 (6) |
O1vi—K4—K1ix | 29.29 (12) | K2—O16—K1 | 88.22 (18) |
O3—K4—K1ix | 164.61 (11) | K2—O16—H16A | 90 (6) |
O6vii—K4—K1ix | 82.54 (11) | K1—O16—H16A | 97 (5) |
O15viii—K4—K1ix | 77.56 (10) | K2—O16—H16B | 134 (4) |
O9—K4—K1ix | 116.41 (9) | K1—O16—H16B | 130 (5) |
O11viii—K4—K1ix | 45.56 (9) | H16A—O16—H16B | 107 (5) |
O21viii—K4—K1ix | 84.12 (10) | K3—O17—K1 | 89.55 (15) |
K3viii—K4—K1ix | 126.99 (5) | K3—O17—H17A | 152 (4) |
C1—S1—Ni1 | 100.8 (2) | K1—O17—H17A | 105 (4) |
C1—S1—Au1 | 106.8 (2) | K3—O17—H17B | 102 (5) |
Ni1—S1—Au1 | 79.06 (6) | K1—O17—H17B | 48 (6) |
C6—S2—Ni1 | 101.8 (2) | H17A—O17—H17B | 105 (5) |
C6—S2—Au2 | 106.34 (18) | K3—O18—H18A | 117 (4) |
Ni1—S2—Au2 | 105.62 (6) | K3—O18—H18B | 103 (5) |
C11—S3—Ni2 | 99.3 (2) | H18A—O18—H18B | 96 (4) |
C11—S3—Au3 | 109.7 (2) | K2—O19—K3xii | 134.9 (2) |
Ni2—S3—Au3 | 112.31 (6) | K2—O19—H19A | 98 (5) |
C16—S4—Ni2 | 100.39 (19) | K3xii—O19—H19A | 45 (5) |
C16—S4—Au4 | 105.93 (18) | K2—O19—H19B | 77 (5) |
Ni2—S4—Au4 | 89.19 (5) | K3xii—O19—H19B | 119 (5) |
C21—S5—Au3 | 102.1 (2) | H19A—O19—H19B | 89 (4) |
C21—S5—Au1 | 108.95 (18) | H20A—O20—H20B | 115 (6) |
Au3—S5—Au1 | 86.81 (6) | K4ii—O21—H21A | 79 (4) |
C26—S6—Au2 | 103.94 (18) | K4ii—O21—H21B | 67 (6) |
C26—S6—Au4 | 110.2 (2) | H21A—O21—H21B | 108 (5) |
Au2—S6—Au4 | 86.74 (5) | H22A—O22—H22B | 120 (6) |
C3—O1—K4i | 127.5 (4) | H23A—O23—H23B | 103 (5) |
C3—O1—K1viii | 107.4 (4) | C32—O24—K3 | 115.1 (6) |
K4i—O1—K1viii | 124.46 (19) | C32—O24—H24 | 141 (6) |
C8—O3—K4 | 135.2 (4) | K3—O24—H24 | 62 (6) |
C8—O3—K3viii | 129.7 (3) | O24—C32—C33 | 113.3 (9) |
K4—O3—K3viii | 91.46 (13) | O24—C32—H321 | 108.9 |
C8—O4—K2x | 126.6 (4) | C33—C32—H321 | 108.9 |
C13—O5—K2vi | 157.2 (5) | O24—C32—H322 | 108.9 |
C13—O6—K4xi | 121.5 (4) | C33—C32—H322 | 108.9 |
C18—O7—K1 | 96.9 (4) | H321—C32—H322 | 107.7 |
C18—O7—K2 | 145.5 (4) | C34—O25—H25 | 108 (6) |
K1—O7—K2 | 87.74 (12) | C35—C34—O25 | 109.7 (14) |
C18—O8—K3 | 176.1 (5) | C35—C34—H341 | 109.7 |
C18—O8—K1 | 86.5 (4) | O25—C34—H341 | 109.7 |
K3—O8—K1 | 90.67 (14) | C35—C34—H342 | 109.7 |
C23—O9—K4 | 147.8 (4) | O25—C34—H342 | 109.7 |
C23—O9—K3viii | 96.9 (4) | H341—C34—H342 | 108.2 |
S5—Au1—Au2—S2 | −125.35 (6) | O21viii—K4—O3—C8 | 103.9 (5) |
S1—Au1—Au2—S2 | 50.31 (6) | K3viii—K4—O3—C8 | −158.8 (6) |
Ni1—Au1—Au2—S2 | 1.40 (4) | K1ix—K4—O3—C8 | 134.4 (5) |
Au4—Au1—Au2—S2 | 146.76 (4) | O1vi—K4—O3—K3viii | 120.9 (5) |
Au3—Au1—Au2—S2 | −172.43 (4) | O6vii—K4—O3—K3viii | −170.69 (16) |
S5—Au1—Au2—S6 | 55.46 (6) | O15viii—K4—O3—K3viii | −7.98 (16) |
S1—Au1—Au2—S6 | −128.88 (6) | O9—K4—O3—K3viii | 56.02 (14) |
Ni1—Au1—Au2—S6 | −177.78 (4) | O11viii—K4—O3—K3viii | −59.17 (16) |
Au4—Au1—Au2—S6 | −32.43 (4) | O21viii—K4—O3—K3viii | −97.26 (14) |
Au3—Au1—Au2—S6 | 8.38 (4) | K1ix—K4—O3—K3viii | −66.8 (4) |
S5—Au1—Au2—Au4 | 87.89 (4) | O13i—K1—O7—C18 | −108.0 (4) |
S1—Au1—Au2—Au4 | −96.45 (4) | O10ii—K1—O7—C18 | 77.5 (4) |
Ni1—Au1—Au2—Au4 | −145.355 (19) | O16—K1—O7—C18 | 176.1 (4) |
Au3—Au1—Au2—Au4 | 40.808 (10) | O1ii—K1—O7—C18 | 153.7 (5) |
S5—Au1—Au3—S3 | 171.58 (7) | O8—K1—O7—C18 | 10.5 (3) |
S1—Au1—Au3—S3 | −9.92 (7) | O17—K1—O7—C18 | 8.2 (4) |
Au2—Au1—Au3—S3 | −98.22 (5) | O12i—K1—O7—C18 | −38.7 (4) |
Au4—Au1—Au3—S3 | −55.44 (5) | K2—K1—O7—C18 | −145.7 (4) |
S1—Au1—Au3—S5 | 178.50 (7) | K3—K1—O7—C18 | 19.3 (3) |
Au2—Au1—Au3—S5 | 90.21 (5) | K4iii—K1—O7—C18 | −83.2 (5) |
Au4—Au1—Au3—S5 | 132.99 (5) | O13i—K1—O7—K2 | 37.67 (13) |
S5—Au1—Au3—Au4 | −132.99 (5) | O10ii—K1—O7—K2 | −136.84 (15) |
S1—Au1—Au3—Au4 | 45.51 (5) | O16—K1—O7—K2 | −38.24 (14) |
Au2—Au1—Au3—Au4 | −42.780 (10) | O1ii—K1—O7—K2 | −60.6 (5) |
S3—Au3—Au4—S4 | 48.53 (5) | O8—K1—O7—K2 | 156.2 (2) |
S5—Au3—Au4—S4 | −126.14 (5) | O17—K1—O7—K2 | 153.89 (14) |
Au1—Au3—Au4—S4 | −93.66 (4) | O12i—K1—O7—K2 | 106.97 (12) |
S3—Au3—Au4—S6 | −129.46 (5) | K3—K1—O7—K2 | 164.98 (11) |
S5—Au3—Au4—S6 | 55.87 (5) | K4iii—K1—O7—K2 | 62.5 (4) |
Au1—Au3—Au4—S6 | 88.35 (4) | O5i—K2—O7—C18 | −33.9 (9) |
S3—Au3—Au4—Ni2 | 4.45 (4) | O16—K2—O7—C18 | 138.3 (7) |
S5—Au3—Au4—Ni2 | −170.22 (4) | O13i—K2—O7—C18 | 62.3 (7) |
Au1—Au3—Au4—Ni2 | −137.737 (16) | O4iv—K2—O7—C18 | −75.2 (7) |
S3—Au3—Au4—Au1 | 142.19 (4) | O19—K2—O7—C18 | −143.8 (7) |
S5—Au3—Au4—Au1 | −32.48 (4) | K1—K2—O7—C18 | 98.9 (7) |
S3—Au3—Au4—Au2 | −176.84 (3) | O5i—K2—O7—K1 | −132.8 (4) |
S5—Au3—Au4—Au2 | 8.50 (4) | O16—K2—O7—K1 | 39.39 (15) |
Au1—Au3—Au4—Au2 | 40.975 (11) | O13i—K2—O7—K1 | −36.64 (14) |
S5—Au1—Au4—S4 | 112.65 (5) | O4iv—K2—O7—K1 | −174.14 (15) |
S1—Au1—Au4—S4 | −70.91 (5) | O19—K2—O7—K1 | 117.26 (15) |
Ni1—Au1—Au4—S4 | −107.28 (4) | O17—K3—O8—K1 | 16.60 (16) |
Au2—Au1—Au4—S4 | −148.35 (4) | O3ii—K3—O8—K1 | −111.7 (2) |
Au3—Au1—Au4—S4 | 80.68 (4) | O24—K3—O8—K1 | 99.45 (16) |
S5—Au1—Au4—S6 | −66.74 (5) | O15—K3—O8—K1 | −138.96 (19) |
S1—Au1—Au4—S6 | 109.71 (5) | O18—K3—O8—K1 | 43.4 (4) |
Ni1—Au1—Au4—S6 | 73.34 (4) | O9ii—K3—O8—K1 | −80.79 (13) |
Au2—Au1—Au4—S6 | 32.27 (4) | O19v—K3—O8—K1 | 169.85 (15) |
Au3—Au1—Au4—S6 | −98.70 (4) | K4ii—K3—O8—K1 | −122.48 (9) |
S5—Au1—Au4—Au3 | 31.97 (4) | O13i—K1—O8—C18 | 50.6 (4) |
S1—Au1—Au4—Au3 | −151.59 (3) | O10ii—K1—O8—C18 | −116.7 (4) |
Ni1—Au1—Au4—Au3 | 172.046 (19) | O7—K1—O8—C18 | −10.6 (3) |
Au2—Au1—Au4—Au3 | 130.976 (13) | O16—K1—O8—C18 | −27.1 (4) |
S5—Au1—Au4—Ni2 | 79.15 (4) | O1ii—K1—O8—C18 | −175.1 (3) |
S1—Au1—Au4—Ni2 | −104.41 (4) | O17—K1—O8—C18 | 167.6 (4) |
Ni1—Au1—Au4—Ni2 | −140.77 (2) | O12i—K1—O8—C18 | 115.2 (4) |
Au2—Au1—Au4—Ni2 | 178.158 (18) | K2—K1—O8—C18 | 6.5 (3) |
Au3—Au1—Au4—Ni2 | 47.18 (2) | K3—K1—O8—C18 | −177.3 (4) |
S5—Au1—Au4—Au2 | −99.01 (4) | K4iii—K1—O8—C18 | 148.1 (3) |
S1—Au1—Au4—Au2 | 77.44 (4) | O13i—K1—O8—K3 | −132.11 (13) |
Ni1—Au1—Au4—Au2 | 41.07 (2) | O10ii—K1—O8—K3 | 60.68 (14) |
Au3—Au1—Au4—Au2 | −130.976 (13) | O7—K1—O8—K3 | 166.8 (2) |
S2—Au2—Au4—S4 | −1.90 (8) | O16—K1—O8—K3 | 150.27 (16) |
S6—Au2—Au4—S4 | −178.99 (8) | O1ii—K1—O8—K3 | 2.2 (3) |
Au1—Au2—Au4—S4 | 48.21 (6) | O17—K1—O8—K3 | −15.03 (14) |
S2—Au2—Au4—S6 | 177.09 (8) | O12i—K1—O8—K3 | −67.43 (13) |
Au1—Au2—Au4—S6 | −132.80 (6) | K2—K1—O8—K3 | −176.15 (11) |
S2—Au2—Au4—Au3 | −93.01 (6) | K4iii—K1—O8—K3 | −34.54 (18) |
S6—Au2—Au4—Au3 | 89.89 (6) | O1vi—K4—O9—C23 | 54.5 (8) |
Au1—Au2—Au4—Au3 | −42.905 (12) | O3—K4—O9—C23 | −138.4 (8) |
S2—Au2—Au4—Au1 | −50.11 (6) | O6vii—K4—O9—C23 | 133.7 (7) |
S6—Au2—Au4—Au1 | 132.80 (6) | O15viii—K4—O9—C23 | −34.8 (8) |
S5—Au1—Ni1—N1 | −95.04 (17) | O11viii—K4—O9—C23 | −24.9 (8) |
S1—Au1—Ni1—N1 | 85.86 (17) | O21viii—K4—O9—C23 | −90.7 (8) |
Au2—Au1—Ni1—N1 | 175.94 (17) | K3viii—K4—O9—C23 | −90.6 (8) |
Au4—Au1—Ni1—N1 | 139.08 (16) | K1ix—K4—O9—C23 | 27.2 (8) |
S5—Au1—Ni1—N2 | −1.86 (17) | O1vi—K4—O9—K3viii | 145.18 (13) |
S1—Au1—Ni1—N2 | 179.05 (17) | O3—K4—O9—K3viii | −47.75 (12) |
Au2—Au1—Ni1—N2 | −90.87 (16) | O6vii—K4—O9—K3viii | −135.64 (16) |
Au4—Au1—Ni1—N2 | −127.73 (16) | O15viii—K4—O9—K3viii | 55.86 (13) |
S5—Au1—Ni1—S1 | 179.10 (7) | O11viii—K4—O9—K3viii | 65.76 (14) |
Au2—Au1—Ni1—S1 | 90.08 (5) | O21viii—K4—O9—K3viii | 0.0 (3) |
Au4—Au1—Ni1—S1 | 53.23 (5) | K1ix—K4—O9—K3viii | 117.83 (8) |
S5—Au1—Ni1—S2 | 87.52 (7) | N2—Ni1—N1—C2 | −159.3 (4) |
S1—Au1—Ni1—S2 | −91.58 (7) | S1—Ni1—N1—C2 | 12.7 (4) |
Au2—Au1—Ni1—S2 | −1.49 (5) | Au1—Ni1—N1—C2 | −40.3 (4) |
Au4—Au1—Ni1—S2 | −38.35 (5) | N1—Ni1—N2—C7 | −156.2 (4) |
S4—Au4—Ni2—N4 | 79.46 (15) | S2—Ni1—N2—C7 | 17.6 (3) |
S6—Au4—Ni2—N4 | −99.26 (15) | Au1—Ni1—N2—C7 | 110.9 (3) |
Au3—Au4—Ni2—N4 | 174.78 (14) | N4—Ni2—N3—C12 | −167.4 (4) |
Au1—Au4—Ni2—N4 | 132.48 (14) | S3—Ni2—N3—C12 | 7.9 (4) |
S4—Au4—Ni2—N3 | 176.9 (2) | Au4—Ni2—N3—C12 | 91.0 (4) |
S6—Au4—Ni2—N3 | −1.8 (2) | N3—Ni2—N4—C17 | −152.1 (4) |
Au3—Au4—Ni2—N3 | −87.8 (2) | S4—Ni2—N4—C17 | 24.1 (3) |
Au1—Au4—Ni2—N3 | −130.1 (2) | Au4—Ni2—N4—C17 | −22.0 (4) |
S4—Au4—Ni2—S3 | −100.02 (7) | Ni1—S1—C1—C5 | −153.6 (4) |
S6—Au4—Ni2—S3 | 81.25 (8) | Au1—S1—C1—C5 | −71.9 (5) |
Au3—Au4—Ni2—S3 | −4.70 (4) | Ni1—S1—C1—C2 | −33.2 (4) |
Au1—Au4—Ni2—S3 | −47.01 (4) | Au1—S1—C1—C2 | 48.5 (4) |
S6—Au4—Ni2—S4 | −178.73 (8) | Ni1—S1—C1—C4 | 87.1 (5) |
Au3—Au4—Ni2—S4 | 95.32 (6) | Au1—S1—C1—C4 | 168.8 (4) |
Au1—Au4—Ni2—S4 | 53.02 (6) | Ni1—N1—C2—C1 | −38.6 (5) |
O13i—K1—K2—O5i | 36.3 (3) | Ni1—N1—C2—C3 | −166.8 (4) |
O10ii—K1—K2—O5i | −147.8 (3) | C5—C1—C2—N1 | 162.3 (4) |
O7—K1—K2—O5i | 159.0 (3) | C4—C1—C2—N1 | −72.9 (5) |
O16—K1—K2—O5i | −79.6 (3) | S1—C1—C2—N1 | 44.8 (5) |
O1ii—K1—K2—O5i | −36.6 (3) | C5—C1—C2—C3 | −73.0 (6) |
O8—K1—K2—O5i | 142.2 (2) | C4—C1—C2—C3 | 51.8 (7) |
O17—K1—K2—O5i | 76.5 (4) | S1—C1—C2—C3 | 169.4 (4) |
O12i—K1—K2—O5i | 75.7 (2) | K4i—O1—C3—O2 | −71.7 (8) |
K3—K1—K2—O5i | 138.8 (2) | K1viii—O1—C3—O2 | 99.7 (7) |
K4iii—K1—K2—O5i | −4.4 (2) | K4i—O1—C3—C2 | 110.1 (5) |
O13i—K1—K2—O16 | 115.9 (2) | K1viii—O1—C3—C2 | −78.4 (5) |
O10ii—K1—K2—O16 | −68.2 (2) | K4i—O1—C3—K1viii | −171.5 (5) |
O7—K1—K2—O16 | −121.4 (2) | K1viii—O1—C3—K4i | 171.5 (5) |
O1ii—K1—K2—O16 | 42.95 (19) | N1—C2—C3—O1 | −7.2 (8) |
O8—K1—K2—O16 | −138.17 (18) | C1—C2—C3—O1 | −131.8 (6) |
O17—K1—K2—O16 | 156.1 (3) | N1—C2—C3—O2 | 174.5 (5) |
O12i—K1—K2—O16 | 155.26 (18) | C1—C2—C3—O2 | 49.9 (7) |
K3—K1—K2—O16 | −141.60 (17) | N1—C2—C3—K1viii | −59.2 (4) |
K4iii—K1—K2—O16 | 75.17 (16) | C1—C2—C3—K1viii | 176.2 (4) |
O10ii—K1—K2—O13i | 175.9 (2) | N1—C2—C3—K4i | 34.9 (6) |
O7—K1—K2—O13i | 122.6 (2) | C1—C2—C3—K4i | −89.7 (6) |
O16—K1—K2—O13i | −115.9 (2) | Ni1—S2—C6—C10 | −151.0 (3) |
O1ii—K1—K2—O13i | −72.97 (19) | Au2—S2—C6—C10 | 98.6 (4) |
O8—K1—K2—O13i | 105.92 (18) | Ni1—S2—C6—C9 | 86.1 (4) |
O17—K1—K2—O13i | 40.2 (3) | Au2—S2—C6—C9 | −24.2 (5) |
O12i—K1—K2—O13i | 39.34 (17) | Ni1—S2—C6—C7 | −33.6 (4) |
K3—K1—K2—O13i | 102.48 (16) | Au2—S2—C6—C7 | −143.9 (3) |
K4iii—K1—K2—O13i | −40.75 (16) | Ni1—N2—C7—C6 | −45.3 (5) |
O13i—K1—K2—O4iv | −115.6 (2) | Ni1—N2—C7—C8 | −169.9 (3) |
O10ii—K1—K2—O4iv | 60.3 (2) | C10—C6—C7—N2 | 164.4 (5) |
O7—K1—K2—O4iv | 7.04 (18) | C9—C6—C7—N2 | −71.1 (6) |
O16—K1—K2—O4iv | 128.5 (2) | S2—C6—C7—N2 | 49.1 (5) |
O1ii—K1—K2—O4iv | 171.44 (16) | C10—C6—C7—C8 | −71.7 (6) |
O8—K1—K2—O4iv | −9.68 (16) | C9—C6—C7—C8 | 52.8 (6) |
O17—K1—K2—O4iv | −75.4 (3) | S2—C6—C7—C8 | 173.0 (4) |
O12i—K1—K2—O4iv | −76.25 (16) | K2x—O4—C8—O3 | 16.3 (8) |
K3—K1—K2—O4iv | −13.11 (16) | K2x—O4—C8—C7 | −162.2 (3) |
K4iii—K1—K2—O4iv | −156.34 (13) | K4—O3—C8—O4 | −96.1 (7) |
O13i—K1—K2—O7 | −122.6 (2) | K3viii—O3—C8—O4 | 111.8 (6) |
O10ii—K1—K2—O7 | 53.26 (19) | K4—O3—C8—C7 | 82.4 (6) |
O16—K1—K2—O7 | 121.4 (2) | K3viii—O3—C8—C7 | −69.6 (6) |
O1ii—K1—K2—O7 | 164.40 (18) | N2—C7—C8—O4 | −154.2 (5) |
O8—K1—K2—O7 | −16.72 (16) | C6—C7—C8—O4 | 83.0 (6) |
O17—K1—K2—O7 | −82.5 (3) | N2—C7—C8—O3 | 27.1 (6) |
O12i—K1—K2—O7 | −83.29 (16) | C6—C7—C8—O3 | −95.7 (6) |
K3—K1—K2—O7 | −20.15 (14) | Ni2—S3—C11—C15 | −161.1 (4) |
K4iii—K1—K2—O7 | −163.38 (15) | Au3—S3—C11—C15 | 81.1 (5) |
O13i—K1—K2—O19 | 162.44 (19) | Ni2—S3—C11—C14 | 73.7 (5) |
O10ii—K1—K2—O19 | −21.67 (19) | Au3—S3—C11—C14 | −44.2 (5) |
O7—K1—K2—O19 | −74.93 (18) | Ni2—S3—C11—C12 | −43.5 (3) |
O16—K1—K2—O19 | 46.52 (19) | Au3—S3—C11—C12 | −161.4 (3) |
O1ii—K1—K2—O19 | 89.47 (17) | Ni2—N3—C12—C13 | −170.0 (4) |
O8—K1—K2—O19 | −91.65 (15) | Ni2—N3—C12—C11 | −40.6 (5) |
O17—K1—K2—O19 | −157.4 (3) | C15—C11—C12—N3 | 169.1 (5) |
O12i—K1—K2—O19 | −158.22 (15) | C14—C11—C12—N3 | −64.0 (5) |
K3—K1—K2—O19 | −95.08 (14) | S3—C11—C12—N3 | 53.3 (5) |
K4iii—K1—K2—O19 | 121.69 (13) | C15—C11—C12—C13 | −63.8 (6) |
O13i—K1—K3—O8 | 63.48 (18) | C14—C11—C12—C13 | 63.0 (6) |
O10ii—K1—K3—O8 | −100.61 (17) | S3—C11—C12—C13 | −179.6 (4) |
O7—K1—K3—O8 | −9.38 (16) | K4xi—O6—C13—O5 | 10.2 (10) |
O16—K1—K3—O8 | −64.5 (3) | K4xi—O6—C13—C12 | −174.4 (4) |
O1ii—K1—K3—O8 | −178.69 (17) | K2vi—O5—C13—O6 | −102.6 (11) |
O17—K1—K3—O8 | 157.5 (2) | K2vi—O5—C13—C12 | 82.0 (11) |
O12i—K1—K3—O8 | 90.77 (17) | N3—C12—C13—O6 | −142.5 (6) |
K2—K1—K3—O8 | 5.14 (14) | C11—C12—C13—O6 | 92.2 (7) |
K4iii—K1—K3—O8 | 155.60 (14) | N3—C12—C13—O5 | 33.3 (8) |
O13i—K1—K3—O17 | −94.0 (2) | C11—C12—C13—O5 | −92.0 (7) |
O10ii—K1—K3—O17 | 101.9 (2) | Ni2—S4—C16—C20 | −146.4 (4) |
O7—K1—K3—O17 | −166.89 (19) | Au4—S4—C16—C20 | −54.2 (4) |
O16—K1—K3—O17 | 138.0 (3) | Ni2—S4—C16—C19 | 93.7 (4) |
O1ii—K1—K3—O17 | 23.79 (18) | Au4—S4—C16—C19 | −174.2 (3) |
O8—K1—K3—O17 | −157.5 (2) | Ni2—S4—C16—C17 | −26.2 (4) |
O12i—K1—K3—O17 | −66.75 (19) | Au4—S4—C16—C17 | 66.0 (4) |
K2—K1—K3—O17 | −152.38 (17) | Ni2—N4—C17—C16 | −48.4 (5) |
K4iii—K1—K3—O17 | −1.92 (16) | Ni2—N4—C17—C18 | −176.3 (3) |
O13i—K1—K3—O3ii | −169.08 (16) | C20—C16—C17—N4 | 165.2 (5) |
O10ii—K1—K3—O3ii | 26.84 (17) | C19—C16—C17—N4 | −69.0 (6) |
O7—K1—K3—O3ii | 118.07 (16) | S4—C16—C17—N4 | 46.1 (5) |
O16—K1—K3—O3ii | 63.0 (3) | C20—C16—C17—C18 | −69.2 (6) |
O1ii—K1—K3—O3ii | −51.25 (16) | C19—C16—C17—C18 | 56.6 (6) |
O8—K1—K3—O3ii | 127.45 (19) | S4—C16—C17—C18 | 171.7 (4) |
O17—K1—K3—O3ii | −75.0 (2) | K1—O8—C18—O7 | 21.1 (6) |
O12i—K1—K3—O3ii | −141.79 (17) | K1—O8—C18—C17 | −155.4 (4) |
K2—K1—K3—O3ii | 132.58 (13) | K1—O7—C18—O8 | −23.1 (6) |
K4iii—K1—K3—O3ii | −76.96 (13) | K2—O7—C18—O8 | −119.2 (7) |
O13i—K1—K3—O24 | −19.66 (19) | K1—O7—C18—C17 | 153.4 (4) |
O10ii—K1—K3—O24 | 176.26 (18) | K2—O7—C18—C17 | 57.3 (8) |
O7—K1—K3—O24 | −92.51 (17) | N4—C17—C18—O8 | −145.9 (5) |
O16—K1—K3—O24 | −147.6 (3) | C16—C17—C18—O8 | 88.9 (6) |
O1ii—K1—K3—O24 | 98.17 (17) | N4—C17—C18—O7 | 37.2 (6) |
O8—K1—K3—O24 | −83.14 (19) | C16—C17—C18—O7 | −88.0 (6) |
O17—K1—K3—O24 | 74.4 (2) | Au3—S5—C21—C25 | −57.3 (4) |
O12i—K1—K3—O24 | 7.63 (17) | Au1—S5—C21—C25 | 33.5 (5) |
K2—K1—K3—O24 | −78.00 (15) | Au3—S5—C21—C24 | 63.0 (4) |
K4iii—K1—K3—O24 | 72.46 (15) | Au1—S5—C21—C24 | 153.8 (4) |
O13i—K1—K3—O15 | 97.77 (16) | Au3—S5—C21—C22 | −177.7 (3) |
O10ii—K1—K3—O15 | −66.31 (15) | Au1—S5—C21—C22 | −87.0 (4) |
O7—K1—K3—O15 | 24.92 (14) | C25—C21—C22—N5 | 164.0 (5) |
O16—K1—K3—O15 | −30.2 (3) | C24—C21—C22—N5 | 43.0 (6) |
O1ii—K1—K3—O15 | −144.40 (14) | S5—C21—C22—N5 | −74.1 (5) |
O8—K1—K3—O15 | 34.30 (16) | C25—C21—C22—C23 | −70.0 (6) |
O17—K1—K3—O15 | −168.2 (2) | C24—C21—C22—C23 | 169.0 (5) |
O12i—K1—K3—O15 | 125.06 (15) | S5—C21—C22—C23 | 51.9 (5) |
K2—K1—K3—O15 | 39.43 (12) | K1viii—O10—C23—O9 | −106.5 (8) |
K4iii—K1—K3—O15 | −170.11 (11) | K1viii—O10—C23—C22 | 69.8 (9) |
O13i—K1—K3—O18 | −96.02 (17) | K1viii—O10—C23—K3viii | −62.3 (6) |
O10ii—K1—K3—O18 | 99.89 (17) | K4—O9—C23—O10 | 137.1 (6) |
O7—K1—K3—O18 | −168.88 (16) | K3viii—O9—C23—O10 | 50.7 (7) |
O16—K1—K3—O18 | 136.0 (3) | K4—O9—C23—C22 | −39.2 (11) |
O1ii—K1—K3—O18 | 21.81 (16) | K3viii—O9—C23—C22 | −125.6 (5) |
O8—K1—K3—O18 | −159.50 (19) | K4—O9—C23—K3viii | 86.4 (7) |
O17—K1—K3—O18 | −2.0 (2) | N5—C22—C23—O10 | −157.7 (6) |
O12i—K1—K3—O18 | −68.73 (16) | C21—C22—C23—O10 | 74.8 (7) |
K2—K1—K3—O18 | −154.36 (13) | N5—C22—C23—O9 | 19.0 (8) |
K4iii—K1—K3—O18 | −3.90 (13) | C21—C22—C23—O9 | −108.5 (7) |
O13i—K1—K3—O9ii | 155.20 (15) | N5—C22—C23—K3viii | −57.8 (6) |
O10ii—K1—K3—O9ii | −8.88 (14) | C21—C22—C23—K3viii | 174.7 (4) |
O7—K1—K3—O9ii | 82.35 (13) | Au2—S6—C26—C29 | 73.8 (4) |
O16—K1—K3—O9ii | 27.3 (3) | Au4—S6—C26—C29 | 165.5 (3) |
O1ii—K1—K3—O9ii | −86.97 (13) | Au2—S6—C26—C30 | −47.0 (4) |
O8—K1—K3—O9ii | 91.73 (16) | Au4—S6—C26—C30 | 44.7 (5) |
O17—K1—K3—O9ii | −110.76 (19) | Au2—S6—C26—C27 | −170.2 (3) |
O12i—K1—K3—O9ii | −177.51 (14) | Au4—S6—C26—C27 | −78.5 (4) |
K2—K1—K3—O9ii | 96.86 (11) | C31—N6—C27—C26 | −171.9 (6) |
K4iii—K1—K3—O9ii | −112.68 (10) | C31—N6—C27—C28 | 67.2 (7) |
O13i—K1—K3—K4ii | 138.31 (13) | C29—C26—C27—N6 | −178.8 (6) |
O10ii—K1—K3—K4ii | −25.78 (12) | C30—C26—C27—N6 | −53.3 (7) |
O7—K1—K3—K4ii | 65.45 (12) | S6—C26—C27—N6 | 69.6 (6) |
O16—K1—K3—K4ii | 10.4 (3) | C29—C26—C27—C28 | −57.8 (7) |
O1ii—K1—K3—K4ii | −103.86 (11) | C30—C26—C27—C28 | 67.6 (6) |
O8—K1—K3—K4ii | 74.83 (14) | S6—C26—C27—C28 | −169.5 (4) |
O17—K1—K3—K4ii | −127.65 (18) | K4ii—O11—C28—O12 | 21 (2) |
O12i—K1—K3—K4ii | 165.60 (13) | K4ii—O11—C28—C27 | −158.8 (12) |
K2—K1—K3—K4ii | 79.97 (9) | K4ii—O11—C28—K1vi | −42.4 (15) |
K4iii—K1—K3—K4ii | −129.57 (7) | K1vi—O12—C28—O11 | −71.2 (6) |
N1—Ni1—S1—C1 | 11.5 (2) | K1vi—O12—C28—C27 | 109.0 (5) |
S2—Ni1—S1—C1 | −162.37 (19) | N6—C27—C28—O11 | 37.8 (7) |
Au1—Ni1—S1—C1 | 105.2 (2) | C26—C27—C28—O11 | −84.9 (7) |
N1—Ni1—S1—Au1 | −93.71 (15) | N6—C27—C28—O12 | −142.4 (5) |
S2—Ni1—S1—Au1 | 92.38 (5) | C26—C27—C28—O12 | 95.0 (6) |
Ni1—Au1—S1—C1 | −98.1 (2) | N6—C27—C28—K1vi | −62.1 (5) |
Au2—Au1—S1—C1 | −175.8 (2) | C26—C27—C28—K1vi | 175.2 (4) |
Au4—Au1—S1—C1 | 123.6 (2) | K1vi—O13—C31—O14 | 104.3 (8) |
Au3—Au1—S1—C1 | 86.6 (2) | K2vi—O13—C31—O14 | −35.0 (9) |
Au2—Au1—S1—Ni1 | −77.74 (4) | K1vi—O13—C31—N6 | −75.2 (10) |
Au4—Au1—S1—Ni1 | −138.30 (4) | K2vi—O13—C31—N6 | 145.4 (5) |
Au3—Au1—S1—Ni1 | −175.28 (2) | K1vi—O13—C31—K2vi | 139.3 (9) |
N2—Ni1—S2—C6 | 9.9 (2) | C27—N6—C31—O13 | −9.4 (10) |
S1—Ni1—S2—C6 | −162.25 (19) | C27—N6—C31—O14 | 171.0 (6) |
Au1—Ni1—S2—C6 | −108.93 (18) | C27—N6—C31—K2vi | 39.5 (11) |
N2—Ni1—S2—Au2 | 120.77 (14) | O8—K3—O15—K4ii | 156.7 (2) |
S1—Ni1—S2—Au2 | −51.34 (7) | O17—K3—O15—K4ii | 112.8 (2) |
Au1—Ni1—S2—Au2 | 1.98 (6) | O3ii—K3—O15—K4ii | −7.13 (14) |
Au1—Au2—S2—C6 | 105.8 (2) | O24—K3—O15—K4ii | −131.64 (15) |
Au4—Au2—S2—C6 | 148.1 (2) | O18—K3—O15—K4ii | −25.5 (4) |
Au1—Au2—S2—Ni1 | −1.85 (6) | O9ii—K3—O15—K4ii | 54.46 (12) |
Au4—Au2—S2—Ni1 | 40.44 (10) | O19v—K3—O15—K4ii | −59.84 (16) |
N3—Ni2—S3—C11 | 20.5 (2) | K1—K3—O15—K4ii | 127.65 (11) |
S4—Ni2—S3—C11 | −155.85 (19) | O5i—K2—O16—K1 | 138.82 (14) |
Au4—Ni2—S3—C11 | −109.42 (18) | O13i—K2—O16—K1 | 40.09 (12) |
N3—Ni2—S3—Au3 | 136.40 (14) | O4iv—K2—O16—K1 | −96.0 (2) |
S4—Ni2—S3—Au3 | −39.92 (7) | O7—K2—O16—K1 | −38.62 (13) |
Au4—Ni2—S3—Au3 | 6.51 (5) | O19—K2—O16—K1 | −137.55 (15) |
Au4—Au3—S3—C11 | 102.7 (2) | O13i—K1—O16—K2 | −41.66 (14) |
Au1—Au3—S3—C11 | 149.0 (2) | O10ii—K1—O16—K2 | 126.82 (14) |
Au4—Au3—S3—Ni2 | −6.72 (5) | O7—K1—O16—K2 | 39.39 (14) |
Au1—Au3—S3—Ni2 | 39.52 (8) | O1ii—K1—O16—K2 | −146.13 (14) |
N4—Ni2—S4—C16 | 2.4 (2) | O8—K1—O16—K2 | 51.35 (19) |
S3—Ni2—S4—C16 | −173.10 (18) | O17—K1—O16—K2 | −161.9 (2) |
Au4—Ni2—S4—C16 | 106.05 (18) | O12i—K1—O16—K2 | −44.6 (3) |
N4—Ni2—S4—Au4 | −103.64 (15) | K3—K1—O16—K2 | 96.4 (3) |
S3—Ni2—S4—Au4 | 80.85 (6) | K4iii—K1—O16—K2 | −125.05 (11) |
Au3—Au4—S4—C16 | −174.97 (19) | O8—K3—O17—K1 | −16.35 (16) |
Ni2—Au4—S4—C16 | −100.6 (2) | O3ii—K3—O17—K1 | 133.32 (13) |
Au1—Au4—S4—C16 | 123.89 (19) | O24—K3—O17—K1 | −105.38 (16) |
Au2—Au4—S4—C16 | 84.8 (2) | O15—K3—O17—K1 | 20.0 (3) |
Au3—Au4—S4—Ni2 | −74.39 (5) | O18—K3—O17—K1 | 177.9 (2) |
Au1—Au4—S4—Ni2 | −135.53 (5) | O9ii—K3—O17—K1 | 67.89 (14) |
Au2—Au4—S4—Ni2 | −174.61 (3) | O19v—K3—O17—K1 | −169.68 (17) |
Au4—Au3—S5—C21 | 148.83 (18) | K4ii—K3—O17—K1 | 92.66 (17) |
Au1—Au3—S5—C21 | 108.70 (19) | O13i—K1—O17—K3 | 113.14 (16) |
Au4—Au3—S5—Au1 | 40.13 (4) | O10ii—K1—O17—K3 | −59.82 (15) |
Ni1—Au1—S5—C21 | 82.5 (2) | O7—K1—O17—K3 | 16.6 (2) |
Au2—Au1—S5—C21 | 158.9 (2) | O16—K1—O17—K3 | −136.8 (3) |
Au4—Au1—S5—C21 | −139.9 (2) | O1ii—K1—O17—K3 | −154.30 (18) |
Au3—Au1—S5—C21 | −101.7 (2) | O8—K1—O17—K3 | 14.98 (14) |
Ni1—Au1—S5—Au3 | −175.78 (2) | O12i—K1—O17—K3 | 82.91 (18) |
Au2—Au1—S5—Au3 | −99.37 (4) | K2—K1—O17—K3 | 81.9 (3) |
Au4—Au1—S5—Au3 | −38.13 (4) | K4iii—K1—O17—K3 | 177.7 (2) |
Au1—Au2—S6—C26 | 150.21 (19) | O5i—K2—O19—K3xii | −74.0 (3) |
Au4—Au2—S6—C26 | 110.0 (2) | O16—K2—O19—K3xii | 166.8 (3) |
Au1—Au2—S6—Au4 | 40.21 (4) | O13i—K2—O19—K3xii | 161.8 (2) |
Au3—Au4—S6—C26 | 156.52 (19) | O4iv—K2—O19—K3xii | 13.8 (2) |
Ni2—Au4—S6—C26 | 81.5 (2) | O7—K2—O19—K3xii | 90.3 (3) |
Au1—Au4—S6—C26 | −142.04 (19) | K1—K2—O19—K3xii | 134.4 (2) |
Au2—Au4—S6—C26 | −103.65 (19) | O8—K3—O24—C32 | 88.2 (6) |
Au3—Au4—S6—Au2 | −99.82 (4) | O17—K3—O24—C32 | −178.6 (6) |
Ni2—Au4—S6—Au2 | −174.81 (3) | O3ii—K3—O24—C32 | −70.2 (7) |
Au1—Au4—S6—Au2 | −38.39 (4) | O15—K3—O24—C32 | 34.2 (6) |
O1vi—K4—O3—C8 | −37.9 (9) | O18—K3—O24—C32 | −116.2 (6) |
O6vii—K4—O3—C8 | 30.5 (6) | O19v—K3—O24—C32 | −44.0 (6) |
O15viii—K4—O3—C8 | −166.8 (5) | K4ii—K3—O24—C32 | −16.7 (7) |
O9—K4—O3—C8 | −102.8 (5) | K1—K3—O24—C32 | 135.0 (6) |
O11viii—K4—O3—C8 | 142.0 (5) | K3—O24—C32—C33 | −161.0 (7) |
Symmetry codes: (i) x−1, y, z; (ii) x, y, z+1; (iii) x−1, y, z+1; (iv) −x, y+1/2, −z; (v) −x, y−1/2, −z+1; (vi) x+1, y, z; (vii) −x+1, y−1/2, −z; (viii) x, y, z−1; (ix) x+1, y, z−1; (x) −x, y−1/2, −z; (xi) −x+1, y+1/2, −z; (xii) −x, y+1/2, −z+1. |
D—H···A | D—H | H···A | D···A | D—H···A |
N1—H1A···O10 | 0.92 | 2.04 | 2.825 (7) | 143 |
N1—H1B···O6x | 0.92 | 2.10 | 3.013 (6) | 172 |
N2—H2B···O9 | 0.92 | 2.06 | 2.960 (6) | 167 |
N3—H3A···O18xii | 0.92 | 2.03 | 2.929 (8) | 167 |
N3—H3B···O14 | 0.92 | 2.08 | 2.867 (6) | 143 |
N4—H4A···O14 | 0.92 | 2.20 | 2.934 (6) | 136 |
N4—H4B···O4iv | 0.92 | 2.13 | 3.004 (6) | 157 |
N5—H5A···O20viii | 0.91 | 1.87 | 2.768 (7) | 169 |
N5—H5B···O15viii | 0.91 | 2.09 | 2.979 (7) | 164 |
N5—H5C···O2vi | 0.91 | 1.97 | 2.816 (6) | 154 |
O15—H15A···O8 | 0.83 (3) | 2.05 (3) | 2.791 (6) | 148 (6) |
O15—H15B···O11 | 0.86 (4) | 1.95 (3) | 2.686 (7) | 143 (6) |
O16—H16A···O20i | 0.86 (4) | 1.97 (4) | 2.820 (7) | 169 (8) |
O16—H16B···O25 | 0.89 (4) | 2.01 (4) | 2.801 (10) | 146 (6) |
O17—H17A···O1ii | 1.02 (3) | 2.64 (7) | 3.187 (7) | 113 (5) |
O17—H17B···O12i | 0.82 (4) | 2.06 (5) | 2.751 (7) | 142 (7) |
O18—H18A···O22v | 0.86 (3) | 1.98 (3) | 2.773 (9) | 153 (5) |
O18—H18B···O23v | 0.93 (3) | 2.08 (4) | 2.958 (10) | 156 (7) |
O19—H19A···O3iv | 0.92 (4) | 1.90 (4) | 2.697 (8) | 144 (7) |
O19—H19B···O21xii | 0.95 (4) | 1.89 (5) | 2.799 (7) | 161 (7) |
O20—H20A···O14 | 0.80 (4) | 1.89 (4) | 2.662 (7) | 165 (7) |
O20—H20B···O23 | 0.85 (4) | 1.90 (4) | 2.734 (8) | 167 (7) |
O21—H21A···O5xiii | 0.97 (3) | 1.89 (3) | 2.791 (8) | 154 (6) |
O21—H21B···O11 | 0.83 (3) | 1.97 (3) | 2.763 (7) | 160 (7) |
O22—H22A···O7 | 0.82 (4) | 2.07 (6) | 2.817 (7) | 151 (9) |
O22—H22B···O19 | 0.83 (3) | 1.96 (3) | 2.766 (8) | 163 (7) |
O23—H23A···O24xii | 0.92 (4) | 2.00 (4) | 2.787 (9) | 142 (6) |
O23—H23B···O21xiv | 0.83 (4) | 1.96 (7) | 2.754 (9) | 158 (8) |
O24—H24···O12i | 0.83 (4) | 2.00 (4) | 2.778 (7) | 154 (7) |
O25—H25···O2ii | 0.90 (4) | 1.99 (4) | 2.792 (9) | 149 (8) |
Symmetry codes: (i) x−1, y, z; (ii) x, y, z+1; (iv) −x, y+1/2, −z; (v) −x, y−1/2, −z+1; (vi) x+1, y, z; (viii) x, y, z−1; (x) −x, y−1/2, −z; (xii) −x, y+1/2, −z+1; (xiii) −x+1, y−1/2, −z+1; (xiv) −x+1, y+1/2, −z+1. |
Experimental details
Crystal data | |
Chemical formula | K4[Au4Ni2(C6H8NO4S)(C5H9NO2S)4(C5H10NO2S)]·C2H6O·10H2O |
Mr | 2214.06 |
Crystal system, space group | Monoclinic, P21 |
Temperature (K) | 200 |
a, b, c (Å) | 9.9638 (18), 22.644 (4), 14.723 (3) |
β (°) | 97.998 (7) |
V (Å3) | 3289.5 (10) |
Z | 2 |
Radiation type | Mo Kα |
µ (mm−1) | 9.97 |
Crystal size (mm) | 0.15 × 0.15 × 0.04 |
Data collection | |
Diffractometer | Rigaku RAXIS-RAPID diffractometer |
Absorption correction | Multi-scan (ABSCOR; Higashi, 1995) |
Tmin, Tmax | 0.316, 0.691 |
No. of measured, independent and observed [I > 2σ(I)] reflections | 38154, 17713, 16029 |
Rint | 0.044 |
(sin θ/λ)max (Å−1) | 0.704 |
Refinement | |
R[F2 > 2σ(F2)], wR(F2), S | 0.030, 0.064, 1.04 |
No. of reflections | 17713 |
No. of parameters | 804 |
No. of restraints | 49 |
H-atom treatment | H atoms treated by a mixture of independent and constrained refinement |
Δρmax, Δρmin (e Å−3) | 1.14, −0.97 |
Absolute structure | Flack (1983). 8079 Friedel Pairs |
Absolute structure parameter | −0.005 (3) |
Computer programs: PROCESS-AUTO (Rigaku, 1998), CrystalStructure (Rigaku/MSC, 2004), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), Mercury (Macrae et al., 2006), publCIF (Westrip, 2010).
D—H···A | D—H | H···A | D···A | D—H···A |
N1—H1A···O10 | 0.92 | 2.04 | 2.825 (7) | 143 |
N1—H1B···O6i | 0.92 | 2.10 | 3.013 (6) | 172 |
N2—H2B···O9 | 0.92 | 2.06 | 2.960 (6) | 167 |
N3—H3A···O18ii | 0.92 | 2.03 | 2.929 (8) | 167 |
N3—H3B···O14 | 0.92 | 2.08 | 2.867 (6) | 143 |
N4—H4A···O14 | 0.92 | 2.20 | 2.934 (6) | 136 |
N4—H4B···O4iii | 0.92 | 2.13 | 3.004 (6) | 157 |
N5—H5A···O20iv | 0.91 | 1.87 | 2.768 (7) | 169 |
N5—H5B···O15iv | 0.91 | 2.09 | 2.979 (7) | 164 |
N5—H5C···O2v | 0.91 | 1.97 | 2.816 (6) | 154 |
O15—H15A···O8 | 0.83 (3) | 2.05 (3) | 2.791 (6) | 148 (6) |
O15—H15B···O11 | 0.86 (4) | 1.95 (3) | 2.686 (7) | 143 (6) |
O16—H16A···O20vi | 0.86 (4) | 1.97 (4) | 2.820 (7) | 169 (8) |
O16—H16B···O25 | 0.89 (4) | 2.01 (4) | 2.801 (10) | 146 (6) |
O17—H17A···O1vii | 1.02 (3) | 2.64 (7) | 3.187 (7) | 113 (5) |
O17—H17B···O12vi | 0.82 (4) | 2.06 (5) | 2.751 (7) | 142 (7) |
O18—H18A···O22viii | 0.86 (3) | 1.98 (3) | 2.773 (9) | 153 (5) |
O18—H18B···O23viii | 0.93 (3) | 2.08 (4) | 2.958 (10) | 156 (7) |
O19—H19A···O3iii | 0.92 (4) | 1.90 (4) | 2.697 (8) | 144 (7) |
O19—H19B···O21ii | 0.95 (4) | 1.89 (5) | 2.799 (7) | 161 (7) |
O20—H20A···O14 | 0.80 (4) | 1.89 (4) | 2.662 (7) | 165 (7) |
O20—H20B···O23 | 0.85 (4) | 1.90 (4) | 2.734 (8) | 167 (7) |
O21—H21A···O5ix | 0.97 (3) | 1.89 (3) | 2.791 (8) | 154 (6) |
O21—H21B···O11 | 0.83 (3) | 1.97 (3) | 2.763 (7) | 160 (7) |
O22—H22A···O7 | 0.82 (4) | 2.07 (6) | 2.817 (7) | 151 (9) |
O22—H22B···O19 | 0.83 (3) | 1.96 (3) | 2.766 (8) | 163 (7) |
O23—H23A···O24ii | 0.92 (4) | 2.00 (4) | 2.787 (9) | 142 (6) |
O23—H23B···O21x | 0.83 (4) | 1.96 (7) | 2.754 (9) | 158 (8) |
O24—H24···O12vi | 0.83 (4) | 2.00 (4) | 2.778 (7) | 154 (7) |
O25—H25···O2vii | 0.90 (4) | 1.99 (4) | 2.792 (9) | 149 (8) |
Symmetry codes: (i) −x, y−1/2, −z; (ii) −x, y+1/2, −z+1; (iii) −x, y+1/2, −z; (iv) x, y, z−1; (v) x+1, y, z; (vi) x−1, y, z; (vii) x, y, z+1; (viii) −x, y−1/2, −z+1; (ix) −x+1, y−1/2, −z+1; (x) −x+1, y+1/2, −z+1. |
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A carbamino derivative of amino acid, which is formed by the reaction of an amino group with CO2, is an important species in biological systems because the carbamination of an N-terminal valine residue of hemoglobin is related to its CO2 derivery [delivery?] and oxygen affinity (Jensen, 2004). While the carbamino deoxyhemoglobin has been crystallographically determined by Fantl et al. (1987), the structural determination of carbaminated amino acids has been done only for an achiral carbaminoglycinate salt (Kovbasyuk et al., 1997).
In the course of studying the reactivity of the 3-mercapto derivative of valine (D-penicillamine; D-H2pen = C5H11NO2S) bound to a gold(I) centre towards various metal ions (Toyota et al., 2005; Taguchi et al., 2007), we found that red crystals containing AuI and NiII atoms in a 2:1 ratio are formed when a solution containing [Au(D-pen)2]3– and Ni2+ is allowed to stand in a refrigerator for 2 months. Herein we report the crystal structure of (I) containing a D-carbaminopenicillaminate (D-cp = C6H8NO4S) that bridges two AuI atoms through a thiolato group. To our knowledge, this is the first example of a structurally characterized chiral carbamino amino acid bound to metal centres.
A displacement ellipsoid plot with the numbering scheme of (I) is given in Fig. 1. The hexanuclear complex anion in (I) contains two {Ni(D-pen)2}2– units, in which each NiII atom is coordinated by two bidentate-N,S D-pen ligands. The two NiII units have a slightly distorted square-planar geometry, with the dihedral angles between the Ni1/N1/S1 and Ni1/N2/S2 planes and the Ni2/N3/S3 and Ni2/N4/S4 planes being 10.3 (2)° and 6.1 (2)°, respectively. All D-pen N,S-chelate rings in the NiII units adopt a δ conformation as found in bis(D-penicillaminato)nickelate(II) (Baidya et al., 1991). In (I), the two NiII units are spanned by two digold(I) linkers, {Au2(D-Hpen)}+ and {Au2(D-cp)}-, forming an S-bridged hexanuclear structure in [{Au2(D-cp)}{Au2(D-Hpen)}{Ni(D-pen)2}2]4– with a 12-membered AuI4NiII2S6 metallo-ring. One of the digold(I) linkers contains a D-Hpen ligand that bridges two AuI atoms through S atoms, while its amino group is in a protonated form (NH3+) and is not involved in the coordination. The other digold(I) linker possesses D-cp, in place of D-Hpen, as a bridging ligand, which is considered to be produced by the reaction of D-pen with CO32–. A carbamino N atom of the D-cp ligand is in a trigonal planar geometry and the C—N bond [C31—N6 = 1.383 (8) Å] is obviously shorter than normal C—N single bonds. In addition, the carbamino and N-carboxylate groups lie roughly on the same plane; the dihedral angle between the N6/C27/H6 and C31/O13/O14 planes is 9.0 (8)°. This is indicative of the spreading of π-conjugation over the carbamino and the N-carboxylate groups. A similar structural feature has been observed for previously reported carbamino compounds (e.g. Garbauskas et al., 1983; Schmitt et al., 2002; Shi et al., 2006). It is noted that the carboxylate groups of D-Hpen and the N-carboxylate of D-cp form intramolecular hydrogen bonds with amine groups bound to NiII atoms [N1···O10 = 2.825 (7), N2···O9 = 2.960 (6), N3···O14 = 2.867 (6), N4···O14 = 2.934 (6) Å] (Fig. 2). Furthermore, there is an intramolecular aurophilic interaction (Schmidbaur & Schier, 2008) between AuI atoms with distances of Au1···Au2 = 3.0635 (5), Au1···Au4 = 3.1730 (6) and Au3···Au4 = 3.0542 (5) Å (Fig. 2). These attractive interactions appear to sustain this unique hexanuclear structure in (I).
In (I), each complex anion is connected [to?] with four neighbouring complex anions through N—H···O hydrogen bonds between amine or ammonium groups and carboxylate groups [N1···O6i = 3.013 (6), N4···O4iii = 3.004 (6), N5···O2v = 2.816 (6) Å; symmetry codes and geometric parameters are given in Table 1], forming a two-dimensional layer structure in the ab plane (Fig. 3). In addition, the layers are parallel connected [in a parallel manner?] with each other through K—Ocarboxylate coordination bonds [2.629 (4) – 3.192 (5) Å] to give a three-dimensional network structure (Fig. 4). Besides carboxylate groups, some water and ethanol molecules coordinate to K+ ions [2.732 (6) – 2.918 (7) Å]. All of the water and ethanol molecules participate in the formation of O—H···O hydrogen bonds with carboxylate groups, water molecules, and/or ethanol molecules in the O—O distance range of 2.662 (7)–3.187 (7) Å (Table 1).