Gold monochloride and monobromide can be transformed into monomeric complexes by ligands such as CO, PPh3 or Me2S, and such ligand-stabilized gold monochloride compounds have been investigated as catalysts, luminescent materials and anticancer drugs, especially when coordinated to a lipophilic benzyl-substituted N-heterocyclic carbene (NHC) ligand. The triclinic structures of NHC-Au-Cl {chlorido(1,3-dibenzyl-4,5-diphenylimidazol-2-ylidene)gold, [AuCl(C29H24N2)]} and NHC-Au-Br {bromido(1,3-dibenzyl-4,5-diphenylimidazol-2-ylidene)gold, [AuBr(C29H24N2)]}, determined by X-ray crystallography at 100 K, have one and four molecules, respectively, in their asymmetric units. The chloride compound shows an almost linear C-Au-Cl fragment [179.76 (8)°], with an Au-C distance of 1.976 (3) Å and an Au-Cl distance of 2.3013 (6) Å, while the bromide compound shows surprisingly large geometry deviations, from 1.969 (12) to 2.016 (10) Å for the Au-C distance and from 2.4279 (14) to 2.4796 (12) Å for the Au-Br distance, in the four independent molecules.
Supporting information
CCDC references: 1506847; 1506846
Data collection: CrysAlis PRO (Agilent, 2014) for (1); CrysAlis PRO (Rigaku Oxford Diffraction, 2015) for (2). Cell refinement: CrysAlis PRO (Agilent, 2014) for (1); CrysAlis PRO (Rigaku Oxford Diffraction, 2015) for (2). Data reduction: CrysAlis PRO (Agilent, 2014) for (1); CrysAlis PRO (Rigaku Oxford Diffraction, 2015) for (2). For both compounds, program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: DIAMOND (Brandenburg, 1999); software used to prepare material for publication: publCIF (Westrip, 2010).
(1) Chlorido(1,3-dibenzyl-4,5-diphenylimidazol-2-ylidene)gold
top
Crystal data top
[AuCl(C29H24N2)] | Z = 2 |
Mr = 632.92 | F(000) = 616 |
Triclinic, P1 | Dx = 1.755 Mg m−3 |
Hall symbol: -P 1 | Cu Kα radiation, λ = 1.54184 Å |
a = 6.9686 (1) Å | Cell parameters from 19517 reflections |
b = 11.8758 (2) Å | θ = 4.4–76.8° |
c = 15.1008 (2) Å | µ = 12.71 mm−1 |
α = 98.249 (2)° | T = 100 K |
β = 95.337 (2)° | Needle, colourless |
γ = 102.467 (2)° | 0.15 × 0.03 × 0.02 mm |
V = 1197.63 (3) Å3 | |
Data collection top
Agilent SuperNova Dual (Cu at zero) Source diffractometer with an Atlas
detector | 5011 independent reflections |
Radiation source: SuperNova (Cu) X-ray Source | 4649 reflections with I > 2σ(I) |
Mirror monochromator | Rint = 0.060 |
Detector resolution: 10.3196 pixels mm-1 | θmax = 76.7°, θmin = 3.9° |
ω scans | h = −8→8 |
Absorption correction: analytical [CrysAlis PRO (Agilent, 2014), based on expressions derived by
Clark & Reid (1995)] | k = −14→13 |
Tmin = 0.307, Tmax = 0.786 | l = −18→19 |
47539 measured reflections | |
Refinement top
Refinement on F2 | Primary atom site location: structure-invariant direct methods |
Least-squares matrix: full | Secondary atom site location: difference Fourier map |
R[F2 > 2σ(F2)] = 0.020 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.048 | H-atom parameters constrained |
S = 1.07 | w = 1/[σ2(Fo2) + (0.0241P)2 + 0.6779P] where P = (Fo2 + 2Fc2)/3 |
5011 reflections | (Δ/σ)max = 0.004 |
298 parameters | Δρmax = 0.84 e Å−3 |
0 restraints | Δρmin = −0.85 e Å−3 |
Special details top
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 > 2sigma(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. |
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top | x | y | z | Uiso*/Ueq | |
Au1 | 0.255623 (16) | 1.012733 (11) | 0.473642 (8) | 0.01793 (4) | |
Cl1 | 0.27277 (9) | 1.05921 (6) | 0.33134 (4) | 0.02018 (13) | |
C1 | 0.3856 (4) | 1.3206 (3) | 0.8164 (2) | 0.0236 (6) | |
H1 | 0.2572 | 1.3310 | 0.8259 | 0.028* | |
C2 | 0.5491 (5) | 1.3815 (3) | 0.8778 (2) | 0.0272 (6) | |
H2 | 0.5314 | 1.4326 | 0.9292 | 0.033* | |
C3 | 0.7367 (5) | 1.3681 (3) | 0.8645 (2) | 0.0304 (7) | |
H3 | 0.8478 | 1.4086 | 0.9071 | 0.036* | |
C4 | 0.7616 (5) | 1.2950 (3) | 0.7883 (3) | 0.0354 (8) | |
H4 | 0.8908 | 1.2873 | 0.7779 | 0.042* | |
C5 | 0.5982 (4) | 1.2328 (3) | 0.7270 (2) | 0.0279 (7) | |
H5 | 0.6162 | 1.1821 | 0.6753 | 0.033* | |
C6 | 0.4091 (4) | 1.2448 (3) | 0.74136 (19) | 0.0200 (5) | |
C7 | 0.2302 (4) | 1.1694 (3) | 0.67845 (19) | 0.0198 (5) | |
H7A | 0.1072 | 1.1838 | 0.7009 | 0.024* | |
H7B | 0.2333 | 1.1909 | 0.6175 | 0.024* | |
N1 | 0.2302 (3) | 1.0447 (2) | 0.67305 (15) | 0.0166 (4) | |
C8 | 0.2404 (4) | 0.9721 (2) | 0.59558 (18) | 0.0157 (5) | |
C9 | 0.2262 (4) | 0.9865 (3) | 0.74598 (19) | 0.0188 (5) | |
C11 | 0.2250 (4) | 1.0439 (3) | 0.83980 (18) | 0.0187 (5) | |
C12 | 0.3987 (4) | 1.0682 (3) | 0.90049 (19) | 0.0220 (6) | |
H12 | 0.5130 | 1.0449 | 0.8822 | 0.026* | |
C13 | 0.4039 (5) | 1.1264 (3) | 0.9875 (2) | 0.0258 (6) | |
H13 | 0.5222 | 1.1436 | 1.0286 | 0.031* | |
C14 | 0.2365 (5) | 1.1597 (3) | 1.0144 (2) | 0.0285 (7) | |
H14 | 0.2407 | 1.1998 | 1.0740 | 0.034* | |
C15 | 0.0629 (5) | 1.1347 (3) | 0.9549 (2) | 0.0301 (7) | |
H15 | −0.0519 | 1.1568 | 0.9739 | 0.036* | |
C16 | 0.0571 (4) | 1.0771 (3) | 0.8673 (2) | 0.0248 (6) | |
H16 | −0.0612 | 1.0606 | 0.8262 | 0.030* | |
C10 | 0.2358 (4) | 0.8762 (3) | 0.71339 (18) | 0.0171 (5) | |
C17 | 0.2350 (4) | 0.7779 (3) | 0.76422 (18) | 0.0195 (5) | |
C18 | 0.3948 (4) | 0.7249 (3) | 0.77107 (19) | 0.0219 (6) | |
H18 | 0.5064 | 0.7496 | 0.7410 | 0.026* | |
C19 | 0.3908 (5) | 0.6357 (3) | 0.8220 (2) | 0.0257 (6) | |
H19 | 0.4989 | 0.5990 | 0.8260 | 0.031* | |
C20 | 0.2292 (5) | 0.6004 (3) | 0.8670 (2) | 0.0288 (7) | |
H20 | 0.2272 | 0.5397 | 0.9019 | 0.035* | |
C21 | 0.0706 (5) | 0.6533 (3) | 0.8611 (2) | 0.0317 (7) | |
H21 | −0.0393 | 0.6294 | 0.8924 | 0.038* | |
C22 | 0.0722 (5) | 0.7410 (3) | 0.8095 (2) | 0.0269 (6) | |
H22 | −0.0376 | 0.7763 | 0.8048 | 0.032* | |
N2 | 0.2429 (3) | 0.8686 (2) | 0.62143 (15) | 0.0179 (5) | |
C23 | 0.2595 (4) | 0.7665 (3) | 0.55930 (19) | 0.0195 (5) | |
H23A | 0.3197 | 0.7153 | 0.5940 | 0.023* | |
H23B | 0.3507 | 0.7927 | 0.5159 | 0.023* | |
C24 | 0.0645 (4) | 0.6950 (3) | 0.50668 (19) | 0.0186 (5) | |
C25 | −0.1168 (4) | 0.6976 (3) | 0.5366 (2) | 0.0217 (6) | |
H25 | −0.1225 | 0.7475 | 0.5909 | 0.026* | |
C26 | −0.2912 (4) | 0.6267 (3) | 0.4870 (2) | 0.0254 (6) | |
H26 | −0.4152 | 0.6288 | 0.5078 | 0.030* | |
C27 | −0.2842 (5) | 0.5536 (3) | 0.4078 (2) | 0.0265 (6) | |
H27 | −0.4031 | 0.5058 | 0.3742 | 0.032* | |
C28 | −0.1022 (5) | 0.5504 (3) | 0.3778 (2) | 0.0278 (7) | |
H28 | −0.0964 | 0.5004 | 0.3236 | 0.033* | |
C29 | 0.0710 (4) | 0.6207 (3) | 0.4274 (2) | 0.0236 (6) | |
H29 | 0.1951 | 0.6180 | 0.4070 | 0.028* | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
Au1 | 0.01714 (6) | 0.02168 (7) | 0.01443 (6) | 0.00492 (4) | 0.00176 (4) | 0.00082 (4) |
Cl1 | 0.0189 (3) | 0.0282 (4) | 0.0134 (3) | 0.0053 (2) | 0.0019 (2) | 0.0036 (2) |
C1 | 0.0253 (14) | 0.0200 (15) | 0.0257 (14) | 0.0083 (11) | 0.0021 (11) | 0.0009 (12) |
C2 | 0.0331 (15) | 0.0214 (16) | 0.0243 (14) | 0.0064 (12) | −0.0012 (12) | −0.0021 (12) |
C3 | 0.0269 (15) | 0.0229 (17) | 0.0356 (17) | −0.0008 (12) | −0.0055 (12) | 0.0022 (13) |
C4 | 0.0204 (14) | 0.035 (2) | 0.049 (2) | 0.0049 (13) | 0.0048 (13) | 0.0020 (16) |
C5 | 0.0245 (14) | 0.0280 (17) | 0.0290 (15) | 0.0037 (12) | 0.0077 (12) | −0.0018 (13) |
C6 | 0.0245 (13) | 0.0139 (14) | 0.0219 (13) | 0.0040 (10) | 0.0029 (10) | 0.0044 (11) |
C7 | 0.0204 (12) | 0.0187 (14) | 0.0206 (13) | 0.0063 (10) | −0.0005 (10) | 0.0036 (11) |
N1 | 0.0171 (10) | 0.0180 (12) | 0.0141 (10) | 0.0049 (8) | 0.0013 (8) | 0.0004 (9) |
C8 | 0.0107 (10) | 0.0127 (13) | 0.0222 (13) | 0.0007 (9) | 0.0006 (9) | 0.0027 (10) |
C9 | 0.0182 (12) | 0.0205 (15) | 0.0178 (13) | 0.0060 (10) | 0.0024 (10) | 0.0017 (11) |
C11 | 0.0250 (13) | 0.0173 (14) | 0.0134 (12) | 0.0039 (11) | 0.0030 (10) | 0.0018 (10) |
C12 | 0.0266 (14) | 0.0210 (15) | 0.0194 (13) | 0.0083 (11) | 0.0017 (11) | 0.0031 (11) |
C13 | 0.0315 (15) | 0.0258 (16) | 0.0174 (13) | 0.0062 (12) | −0.0033 (11) | −0.0002 (12) |
C14 | 0.0351 (16) | 0.0266 (17) | 0.0196 (14) | 0.0031 (13) | 0.0055 (12) | −0.0045 (12) |
C15 | 0.0261 (14) | 0.0358 (19) | 0.0248 (15) | 0.0049 (13) | 0.0085 (12) | −0.0061 (13) |
C16 | 0.0228 (13) | 0.0266 (16) | 0.0221 (14) | 0.0032 (11) | 0.0030 (11) | −0.0021 (12) |
C10 | 0.0159 (11) | 0.0187 (14) | 0.0154 (12) | 0.0035 (10) | 0.0004 (9) | 0.0007 (10) |
C17 | 0.0256 (13) | 0.0147 (14) | 0.0163 (12) | 0.0036 (10) | 0.0008 (10) | −0.0008 (10) |
C18 | 0.0231 (13) | 0.0194 (15) | 0.0203 (13) | 0.0037 (11) | −0.0021 (10) | −0.0009 (11) |
C19 | 0.0309 (15) | 0.0213 (16) | 0.0223 (14) | 0.0059 (12) | −0.0041 (11) | 0.0002 (12) |
C20 | 0.0465 (18) | 0.0171 (15) | 0.0215 (14) | 0.0062 (13) | 0.0022 (13) | 0.0026 (12) |
C21 | 0.0414 (18) | 0.0265 (18) | 0.0303 (16) | 0.0088 (14) | 0.0165 (14) | 0.0057 (13) |
C22 | 0.0303 (15) | 0.0248 (17) | 0.0289 (15) | 0.0092 (12) | 0.0123 (12) | 0.0055 (13) |
N2 | 0.0184 (10) | 0.0181 (12) | 0.0159 (10) | 0.0039 (9) | 0.0021 (8) | −0.0005 (9) |
C23 | 0.0207 (12) | 0.0185 (14) | 0.0183 (12) | 0.0055 (10) | 0.0028 (10) | −0.0021 (11) |
C24 | 0.0218 (13) | 0.0162 (14) | 0.0181 (12) | 0.0046 (10) | 0.0027 (10) | 0.0030 (10) |
C25 | 0.0238 (13) | 0.0193 (15) | 0.0210 (13) | 0.0055 (11) | 0.0022 (10) | 0.0003 (11) |
C26 | 0.0217 (13) | 0.0231 (16) | 0.0323 (16) | 0.0070 (11) | 0.0048 (11) | 0.0039 (12) |
C27 | 0.0249 (14) | 0.0209 (16) | 0.0301 (15) | 0.0014 (11) | −0.0032 (11) | 0.0028 (12) |
C28 | 0.0322 (15) | 0.0251 (17) | 0.0217 (14) | 0.0039 (12) | 0.0020 (12) | −0.0048 (12) |
C29 | 0.0226 (13) | 0.0256 (16) | 0.0212 (13) | 0.0046 (11) | 0.0042 (11) | −0.0003 (12) |
Geometric parameters (Å, º) top
Au1—C8 | 1.976 (3) | C15—H15 | 0.9500 |
Au1—Cl1 | 2.3013 (6) | C16—H16 | 0.9500 |
C1—C6 | 1.388 (4) | C10—N2 | 1.385 (3) |
C1—C2 | 1.391 (4) | C10—C17 | 1.486 (4) |
C1—H1 | 0.9500 | C17—C18 | 1.395 (4) |
C2—C3 | 1.380 (5) | C17—C22 | 1.401 (4) |
C2—H2 | 0.9500 | C18—C19 | 1.392 (5) |
C3—C4 | 1.386 (5) | C18—H18 | 0.9500 |
C3—H3 | 0.9500 | C19—C20 | 1.387 (5) |
C4—C5 | 1.395 (5) | C19—H19 | 0.9500 |
C4—H4 | 0.9500 | C20—C21 | 1.386 (5) |
C5—C6 | 1.389 (4) | C20—H20 | 0.9500 |
C5—H5 | 0.9500 | C21—C22 | 1.387 (5) |
C6—C7 | 1.520 (4) | C21—H21 | 0.9500 |
C7—N1 | 1.471 (4) | C22—H22 | 0.9500 |
C7—H7A | 0.9900 | N2—C23 | 1.455 (4) |
C7—H7B | 0.9900 | C23—C24 | 1.519 (4) |
N1—C8 | 1.367 (3) | C23—H23A | 0.9900 |
N1—C9 | 1.381 (4) | C23—H23B | 0.9900 |
C8—N2 | 1.346 (4) | C24—C25 | 1.385 (4) |
C9—C10 | 1.350 (4) | C24—C29 | 1.392 (4) |
C9—C11 | 1.483 (4) | C25—C26 | 1.398 (4) |
C11—C16 | 1.393 (4) | C25—H25 | 0.9500 |
C11—C12 | 1.398 (4) | C26—C27 | 1.385 (5) |
C12—C13 | 1.387 (4) | C26—H26 | 0.9500 |
C12—H12 | 0.9500 | C27—C28 | 1.392 (5) |
C13—C14 | 1.387 (5) | C27—H27 | 0.9500 |
C13—H13 | 0.9500 | C28—C29 | 1.390 (4) |
C14—C15 | 1.388 (5) | C28—H28 | 0.9500 |
C14—H14 | 0.9500 | C29—H29 | 0.9500 |
C15—C16 | 1.392 (4) | | |
| | | |
C8—Au1—Cl1 | 179.76 (8) | C15—C16—H16 | 120.0 |
C6—C1—C2 | 120.3 (3) | C11—C16—H16 | 120.0 |
C6—C1—H1 | 119.8 | C9—C10—N2 | 107.6 (3) |
C2—C1—H1 | 119.8 | C9—C10—C17 | 127.6 (3) |
C3—C2—C1 | 120.5 (3) | N2—C10—C17 | 124.8 (3) |
C3—C2—H2 | 119.7 | C18—C17—C22 | 119.3 (3) |
C1—C2—H2 | 119.7 | C18—C17—C10 | 121.9 (3) |
C2—C3—C4 | 119.4 (3) | C22—C17—C10 | 118.7 (3) |
C2—C3—H3 | 120.3 | C19—C18—C17 | 120.0 (3) |
C4—C3—H3 | 120.3 | C19—C18—H18 | 120.0 |
C3—C4—C5 | 120.4 (3) | C17—C18—H18 | 120.0 |
C3—C4—H4 | 119.8 | C20—C19—C18 | 120.2 (3) |
C5—C4—H4 | 119.8 | C20—C19—H19 | 119.9 |
C6—C5—C4 | 120.1 (3) | C18—C19—H19 | 119.9 |
C6—C5—H5 | 120.0 | C21—C20—C19 | 120.2 (3) |
C4—C5—H5 | 120.0 | C21—C20—H20 | 119.9 |
C1—C6—C5 | 119.3 (3) | C19—C20—H20 | 119.9 |
C1—C6—C7 | 120.9 (3) | C20—C21—C22 | 120.0 (3) |
C5—C6—C7 | 119.8 (3) | C20—C21—H21 | 120.0 |
N1—C7—C6 | 110.5 (2) | C22—C21—H21 | 120.0 |
N1—C7—H7A | 109.6 | C21—C22—C17 | 120.3 (3) |
C6—C7—H7A | 109.6 | C21—C22—H22 | 119.9 |
N1—C7—H7B | 109.6 | C17—C22—H22 | 119.9 |
C6—C7—H7B | 109.6 | C8—N2—C10 | 110.6 (2) |
H7A—C7—H7B | 108.1 | C8—N2—C23 | 122.8 (2) |
C8—N1—C9 | 111.1 (2) | C10—N2—C23 | 126.5 (3) |
C8—N1—C7 | 124.4 (2) | N2—C23—C24 | 114.6 (2) |
C9—N1—C7 | 124.5 (2) | N2—C23—H23A | 108.6 |
N2—C8—N1 | 104.7 (2) | C24—C23—H23A | 108.6 |
N2—C8—Au1 | 128.0 (2) | N2—C23—H23B | 108.6 |
N1—C8—Au1 | 127.3 (2) | C24—C23—H23B | 108.6 |
C10—C9—N1 | 106.0 (2) | H23A—C23—H23B | 107.6 |
C10—C9—C11 | 130.4 (3) | C25—C24—C29 | 119.4 (3) |
N1—C9—C11 | 123.5 (3) | C25—C24—C23 | 122.5 (3) |
C16—C11—C12 | 119.8 (3) | C29—C24—C23 | 118.0 (2) |
C16—C11—C9 | 121.3 (3) | C24—C25—C26 | 120.1 (3) |
C12—C11—C9 | 118.9 (3) | C24—C25—H25 | 119.9 |
C13—C12—C11 | 120.0 (3) | C26—C25—H25 | 119.9 |
C13—C12—H12 | 120.0 | C27—C26—C25 | 120.3 (3) |
C11—C12—H12 | 120.0 | C27—C26—H26 | 119.8 |
C14—C13—C12 | 120.0 (3) | C25—C26—H26 | 119.8 |
C14—C13—H13 | 120.0 | C26—C27—C28 | 119.7 (3) |
C12—C13—H13 | 120.0 | C26—C27—H27 | 120.2 |
C13—C14—C15 | 120.4 (3) | C28—C27—H27 | 120.2 |
C13—C14—H14 | 119.8 | C29—C28—C27 | 119.8 (3) |
C15—C14—H14 | 119.8 | C29—C28—H28 | 120.1 |
C14—C15—C16 | 119.9 (3) | C27—C28—H28 | 120.1 |
C14—C15—H15 | 120.0 | C28—C29—C24 | 120.7 (3) |
C16—C15—H15 | 120.0 | C28—C29—H29 | 119.7 |
C15—C16—C11 | 119.9 (3) | C24—C29—H29 | 119.7 |
| | | |
C6—C1—C2—C3 | 0.5 (5) | N1—C9—C10—C17 | −179.6 (3) |
C1—C2—C3—C4 | 1.2 (5) | C11—C9—C10—C17 | 4.3 (5) |
C2—C3—C4—C5 | −1.9 (6) | C9—C10—C17—C18 | −117.8 (3) |
C3—C4—C5—C6 | 0.8 (6) | N2—C10—C17—C18 | 63.6 (4) |
C2—C1—C6—C5 | −1.7 (5) | C9—C10—C17—C22 | 59.5 (4) |
C2—C1—C6—C7 | 174.3 (3) | N2—C10—C17—C22 | −119.1 (3) |
C4—C5—C6—C1 | 1.0 (5) | C22—C17—C18—C19 | 0.4 (4) |
C4—C5—C6—C7 | −175.0 (3) | C10—C17—C18—C19 | 177.7 (3) |
C1—C6—C7—N1 | −121.6 (3) | C17—C18—C19—C20 | −0.8 (4) |
C5—C6—C7—N1 | 54.4 (4) | C18—C19—C20—C21 | 0.3 (5) |
C6—C7—N1—C8 | −118.6 (3) | C19—C20—C21—C22 | 0.6 (5) |
C6—C7—N1—C9 | 59.3 (3) | C20—C21—C22—C17 | −1.0 (5) |
C9—N1—C8—N2 | −0.1 (3) | C18—C17—C22—C21 | 0.4 (5) |
C7—N1—C8—N2 | 178.0 (2) | C10—C17—C22—C21 | −177.0 (3) |
C9—N1—C8—Au1 | −178.54 (18) | N1—C8—N2—C10 | −0.4 (3) |
C7—N1—C8—Au1 | −0.4 (4) | Au1—C8—N2—C10 | 178.02 (18) |
C8—N1—C9—C10 | 0.6 (3) | N1—C8—N2—C23 | −178.0 (2) |
C7—N1—C9—C10 | −177.6 (2) | Au1—C8—N2—C23 | 0.4 (4) |
C8—N1—C9—C11 | 177.0 (2) | C9—C10—N2—C8 | 0.8 (3) |
C7—N1—C9—C11 | −1.2 (4) | C17—C10—N2—C8 | 179.6 (2) |
C10—C9—C11—C16 | −111.8 (4) | C9—C10—N2—C23 | 178.2 (2) |
N1—C9—C11—C16 | 72.7 (4) | C17—C10—N2—C23 | −2.9 (4) |
C10—C9—C11—C12 | 70.4 (4) | C8—N2—C23—C24 | −84.5 (3) |
N1—C9—C11—C12 | −105.1 (3) | C10—N2—C23—C24 | 98.4 (3) |
C16—C11—C12—C13 | −0.7 (5) | N2—C23—C24—C25 | −23.0 (4) |
C9—C11—C12—C13 | 177.1 (3) | N2—C23—C24—C29 | 159.8 (3) |
C11—C12—C13—C14 | 0.5 (5) | C29—C24—C25—C26 | −0.5 (5) |
C12—C13—C14—C15 | 0.2 (5) | C23—C24—C25—C26 | −177.7 (3) |
C13—C14—C15—C16 | −0.8 (5) | C24—C25—C26—C27 | 0.0 (5) |
C14—C15—C16—C11 | 0.6 (5) | C25—C26—C27—C28 | 0.2 (5) |
C12—C11—C16—C15 | 0.1 (5) | C26—C27—C28—C29 | 0.0 (5) |
C9—C11—C16—C15 | −177.6 (3) | C27—C28—C29—C24 | −0.4 (5) |
N1—C9—C10—N2 | −0.8 (3) | C25—C24—C29—C28 | 0.7 (5) |
C11—C9—C10—N2 | −176.9 (3) | C23—C24—C29—C28 | 178.0 (3) |
(2) Bromido(1,3-dibenzyl-4,5-diphenylimidazol-2-ylidene)gold
top
Crystal data top
[AuBr(C29H24N2)] | Z = 8 |
Mr = 677.38 | F(000) = 2608 |
Triclinic, P1 | Dx = 1.816 Mg m−3 |
Hall symbol: -P 1 | Cu Kα radiation, λ = 1.54184 Å |
a = 7.0973 (2) Å | Cell parameters from 33633 reflections |
b = 15.3919 (3) Å | θ = 3.9–76.2° |
c = 45.4224 (6) Å | µ = 13.19 mm−1 |
α = 87.896 (2)° | T = 100 K |
β = 87.876 (2)° | Irregular, colourless |
γ = 89.871 (2)° | 0.17 × 0.07 × 0.04 mm |
V = 4955.23 (18) Å3 | |
Data collection top
Agilent SuperNova Dual (Cu at zero) Source diffractometer with an Atlas
detector | 20595 independent reflections |
Radiation source: SuperNova (Cu) X-ray Source | 18809 reflections with I > 2σ(I) |
Mirror monochromator | Rint = 0.055 |
Detector resolution: 10.3196 pixels mm-1 | θmax = 76.8°, θmin = 3.0° |
ω scans | h = −8→8 |
Absorption correction: analytical [(CrysAlis PRO; Rigaku Oxford Diffraction, 2015), based on
expressions
derived by Clark & Reid (1995)] | k = −19→19 |
Tmin = 0.281, Tmax = 0.653 | l = −56→48 |
106224 measured reflections | |
Refinement top
Refinement on F2 | Primary atom site location: structure-invariant direct methods |
Least-squares matrix: full | Secondary atom site location: difference Fourier map |
R[F2 > 2σ(F2)] = 0.073 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.150 | H-atom parameters constrained |
S = 1.30 | w = 1/[σ2(Fo2) + (0.P)2 + 125.0771P] where P = (Fo2 + 2Fc2)/3 |
20595 reflections | (Δ/σ)max = 0.006 |
1189 parameters | Δρmax = 3.07 e Å−3 |
0 restraints | Δρmin = −3.44 e Å−3 |
Special details top
Experimental. Absorption correction: Rigaku Oxford Diffraction (2015).
Analytical numeric absorption correction using a multifaceted crystal
model based on expressions derived by Clark & Reid (1995).
Multi-scan absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm. |
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 > 2sigma(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. |
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top | x | y | z | Uiso*/Ueq | |
C1A | 0.3431 (18) | 0.8202 (8) | 0.8456 (3) | 0.030 (3) | |
H1A | 0.4702 | 0.8055 | 0.8494 | 0.036* | |
C2A | 0.215 (2) | 0.8304 (8) | 0.8690 (3) | 0.040 (3) | |
H2A | 0.2548 | 0.8224 | 0.8887 | 0.047* | |
C3A | 0.029 (2) | 0.8523 (8) | 0.8637 (3) | 0.039 (3) | |
H3A | −0.0576 | 0.8601 | 0.8798 | 0.047* | |
C4A | −0.030 (2) | 0.8627 (8) | 0.8351 (3) | 0.037 (3) | |
H4A | −0.1571 | 0.8773 | 0.8315 | 0.044* | |
C5A | 0.093 (2) | 0.8523 (7) | 0.8124 (3) | 0.034 (3) | |
H5A | 0.0495 | 0.8591 | 0.7929 | 0.040* | |
C6A | 0.2873 (17) | 0.8313 (6) | 0.8162 (3) | 0.025 (2) | |
C7A | 0.4327 (15) | 0.8254 (7) | 0.7921 (2) | 0.023 (2) | |
H7A | 0.5139 | 0.8777 | 0.7922 | 0.028* | |
H7B | 0.5132 | 0.7742 | 0.7963 | 0.028* | |
N1A | 0.3605 (13) | 0.8184 (6) | 0.76246 (19) | 0.0230 (19) | |
C8A | 0.3300 (14) | 0.8870 (6) | 0.7437 (2) | 0.020 (2) | |
Au1A | 0.33493 (7) | 1.01196 (3) | 0.754069 (10) | 0.02393 (10) | |
Br1A | 0.33379 (17) | 1.16683 (7) | 0.76731 (3) | 0.0279 (2) | |
C9A | 0.3399 (18) | 0.7405 (7) | 0.7478 (2) | 0.027 (2) | |
C11A | 0.3480 (17) | 0.6528 (7) | 0.7628 (2) | 0.026 (2) | |
C12A | 0.1830 (19) | 0.6195 (8) | 0.7760 (3) | 0.036 (3) | |
H12A | 0.0707 | 0.6533 | 0.7762 | 0.043* | |
C13A | 0.183 (2) | 0.5366 (8) | 0.7891 (3) | 0.038 (3) | |
H13A | 0.0700 | 0.5130 | 0.7979 | 0.045* | |
C14A | 0.345 (2) | 0.4889 (8) | 0.7893 (3) | 0.035 (3) | |
H14A | 0.3440 | 0.4323 | 0.7984 | 0.042* | |
C15A | 0.513 (2) | 0.5218 (8) | 0.7766 (3) | 0.035 (3) | |
H15A | 0.6250 | 0.4881 | 0.7769 | 0.042* | |
C16A | 0.5132 (19) | 0.6049 (8) | 0.7634 (3) | 0.033 (3) | |
H16A | 0.6267 | 0.6287 | 0.7548 | 0.039* | |
C10A | 0.3015 (16) | 0.7628 (7) | 0.7196 (2) | 0.023 (2) | |
C17A | 0.282 (2) | 0.7048 (8) | 0.6944 (3) | 0.038 (3) | |
C18A | 0.107 (3) | 0.6929 (11) | 0.6825 (3) | 0.060 (5) | |
H18A | −0.0008 | 0.7230 | 0.6898 | 0.072* | |
C19A | 0.091 (4) | 0.6348 (14) | 0.6590 (4) | 0.081 (7) | |
H19A | −0.0267 | 0.6256 | 0.6504 | 0.097* | |
C20A | 0.250 (4) | 0.5922 (11) | 0.6489 (4) | 0.080 (7) | |
H20A | 0.2400 | 0.5529 | 0.6334 | 0.095* | |
C21A | 0.421 (4) | 0.6047 (10) | 0.6604 (3) | 0.076 (7) | |
H21A | 0.5289 | 0.5743 | 0.6531 | 0.091* | |
C22A | 0.438 (3) | 0.6627 (10) | 0.6832 (3) | 0.059 (5) | |
H22A | 0.5579 | 0.6730 | 0.6909 | 0.071* | |
N2A | 0.2920 (14) | 0.8522 (5) | 0.7176 (2) | 0.0240 (19) | |
C23A | 0.2358 (18) | 0.9032 (7) | 0.6914 (2) | 0.029 (2) | |
H23A | 0.2118 | 0.9640 | 0.6968 | 0.034* | |
H23B | 0.1168 | 0.8793 | 0.6843 | 0.034* | |
C24A | 0.3856 (19) | 0.9021 (7) | 0.6666 (3) | 0.031 (3) | |
C25A | 0.570 (2) | 0.9275 (8) | 0.6711 (3) | 0.038 (3) | |
H25A | 0.6064 | 0.9429 | 0.6901 | 0.045* | |
C26A | 0.702 (2) | 0.9305 (9) | 0.6477 (3) | 0.046 (3) | |
H26A | 0.8280 | 0.9476 | 0.6508 | 0.055* | |
C27A | 0.652 (2) | 0.9088 (9) | 0.6199 (3) | 0.047 (4) | |
H27A | 0.7422 | 0.9115 | 0.6039 | 0.057* | |
C28A | 0.470 (2) | 0.8831 (9) | 0.6154 (3) | 0.048 (4) | |
H28A | 0.4353 | 0.8673 | 0.5963 | 0.057* | |
C29A | 0.338 (2) | 0.8802 (8) | 0.6387 (3) | 0.037 (3) | |
H29A | 0.2128 | 0.8629 | 0.6354 | 0.045* | |
C1B | 0.4427 (18) | 0.9524 (7) | 0.1697 (3) | 0.030 (3) | |
H1B | 0.4536 | 0.9822 | 0.1875 | 0.036* | |
C2B | 0.5945 (19) | 0.9509 (8) | 0.1497 (3) | 0.036 (3) | |
H2B | 0.7082 | 0.9800 | 0.1537 | 0.043* | |
C3B | 0.580 (2) | 0.9073 (8) | 0.1241 (3) | 0.040 (3) | |
H3B | 0.6838 | 0.9061 | 0.1103 | 0.048* | |
C4B | 0.414 (2) | 0.8651 (9) | 0.1183 (3) | 0.045 (3) | |
H4B | 0.4055 | 0.8349 | 0.1005 | 0.054* | |
C5B | 0.261 (2) | 0.8663 (8) | 0.1381 (3) | 0.034 (3) | |
H5B | 0.1484 | 0.8370 | 0.1339 | 0.041* | |
C6B | 0.2735 (18) | 0.9107 (7) | 0.1642 (2) | 0.028 (2) | |
C7B | 0.1098 (18) | 0.9125 (7) | 0.1863 (2) | 0.027 (2) | |
H7C | 0.0788 | 0.9738 | 0.1904 | 0.033* | |
H7D | −0.0016 | 0.8863 | 0.1776 | 0.033* | |
N1B | 0.1484 (15) | 0.8658 (6) | 0.2140 (2) | 0.028 (2) | |
C8B | 0.1816 (17) | 0.9026 (7) | 0.2393 (2) | 0.025 (2) | |
Au1B | 0.18212 (7) | 1.02978 (3) | 0.248238 (10) | 0.02357 (10) | |
Br1B | 0.17498 (15) | 1.18536 (7) | 0.26054 (3) | 0.0233 (2) | |
C9B | 0.1545 (18) | 0.7761 (7) | 0.2179 (2) | 0.027 (2) | |
C11B | 0.137 (2) | 0.7159 (7) | 0.1936 (3) | 0.036 (3) | |
C12B | −0.032 (2) | 0.7021 (8) | 0.1797 (3) | 0.041 (3) | |
H12B | −0.1421 | 0.7329 | 0.1856 | 0.049* | |
C13B | −0.038 (3) | 0.6435 (10) | 0.1573 (3) | 0.053 (4) | |
H13B | −0.1534 | 0.6341 | 0.1480 | 0.064* | |
C14B | 0.121 (3) | 0.5988 (9) | 0.1484 (3) | 0.062 (5) | |
H14B | 0.1137 | 0.5586 | 0.1331 | 0.074* | |
C15B | 0.290 (3) | 0.6120 (10) | 0.1615 (3) | 0.065 (6) | |
H15B | 0.3999 | 0.5817 | 0.1552 | 0.079* | |
C16B | 0.298 (3) | 0.6703 (8) | 0.1842 (3) | 0.046 (4) | |
H16B | 0.4137 | 0.6793 | 0.1935 | 0.055* | |
C10B | 0.1910 (16) | 0.7581 (7) | 0.2463 (3) | 0.027 (2) | |
C17B | 0.2020 (19) | 0.6717 (7) | 0.2621 (2) | 0.029 (3) | |
C18B | 0.366 (2) | 0.6433 (7) | 0.2750 (3) | 0.033 (3) | |
H18B | 0.4759 | 0.6784 | 0.2741 | 0.040* | |
C19B | 0.364 (2) | 0.5610 (8) | 0.2895 (3) | 0.041 (3) | |
H19B | 0.4751 | 0.5411 | 0.2988 | 0.050* | |
C20B | 0.209 (2) | 0.5087 (8) | 0.2905 (3) | 0.038 (3) | |
H20B | 0.2115 | 0.4534 | 0.3005 | 0.045* | |
C21B | 0.047 (2) | 0.5368 (8) | 0.2771 (3) | 0.040 (3) | |
H21B | −0.0614 | 0.5005 | 0.2774 | 0.048* | |
C22B | 0.044 (2) | 0.6191 (7) | 0.2631 (3) | 0.034 (3) | |
H22B | −0.0684 | 0.6393 | 0.2543 | 0.040* | |
N2B | 0.2084 (14) | 0.8378 (6) | 0.25939 (19) | 0.025 (2) | |
C23B | 0.264 (2) | 0.8501 (7) | 0.2895 (3) | 0.033 (3) | |
H23C | 0.3372 | 0.9048 | 0.2900 | 0.039* | |
H23D | 0.3489 | 0.8018 | 0.2954 | 0.039* | |
C24B | 0.103 (2) | 0.8539 (7) | 0.3117 (3) | 0.032 (3) | |
C25B | 0.139 (3) | 0.8545 (11) | 0.3419 (3) | 0.053 (4) | |
H25B | 0.2650 | 0.8494 | 0.3482 | 0.064* | |
C26B | −0.013 (3) | 0.8626 (11) | 0.3629 (3) | 0.059 (5) | |
H26B | 0.0129 | 0.8626 | 0.3833 | 0.071* | |
C27B | −0.191 (3) | 0.8703 (10) | 0.3545 (4) | 0.059 (5) | |
H27B | −0.2899 | 0.8775 | 0.3688 | 0.071* | |
C28B | −0.230 (3) | 0.8677 (9) | 0.3255 (3) | 0.051 (4) | |
H28B | −0.3567 | 0.8711 | 0.3194 | 0.061* | |
C29B | −0.076 (2) | 0.8597 (9) | 0.3041 (3) | 0.043 (3) | |
H29B | −0.1040 | 0.8586 | 0.2838 | 0.051* | |
C1C | 0.5116 (17) | 0.7562 (8) | 1.0067 (3) | 0.033 (3) | |
H1C | 0.4675 | 0.7017 | 1.0006 | 0.040* | |
C2C | 0.381 (2) | 0.8212 (10) | 1.0132 (4) | 0.047 (4) | |
H2C | 0.2502 | 0.8115 | 1.0111 | 0.056* | |
C3C | 0.445 (2) | 0.9002 (9) | 1.0226 (3) | 0.044 (3) | |
H3C | 0.3573 | 0.9450 | 1.0272 | 0.053* | |
C4C | 0.634 (3) | 0.9133 (10) | 1.0252 (4) | 0.058 (5) | |
H4C | 0.6774 | 0.9671 | 1.0320 | 0.070* | |
C5C | 0.764 (2) | 0.8488 (8) | 1.0180 (3) | 0.044 (3) | |
H5C | 0.8950 | 0.8596 | 1.0194 | 0.053* | |
C6C | 0.7023 (17) | 0.7686 (7) | 1.0088 (2) | 0.026 (2) | |
C7C | 0.8403 (17) | 0.6980 (8) | 1.0018 (2) | 0.028 (2) | |
H7E | 0.9680 | 0.7236 | 0.9993 | 0.033* | |
H7F | 0.8416 | 0.6555 | 1.0187 | 0.033* | |
N1C | 0.7981 (14) | 0.6523 (6) | 0.97526 (19) | 0.0234 (19) | |
C8C | 0.7602 (13) | 0.5679 (6) | 0.9750 (2) | 0.0167 (19) | |
Au1C | 0.74818 (6) | 0.47981 (3) | 1.008950 (10) | 0.02272 (10) | |
Br1C | 0.72632 (17) | 0.37071 (8) | 1.04914 (3) | 0.0301 (3) | |
C9C | 0.7922 (16) | 0.6885 (7) | 0.9469 (2) | 0.025 (2) | |
C11C | 0.8128 (18) | 0.7834 (7) | 0.9403 (2) | 0.027 (2) | |
C12C | 0.661 (2) | 0.8277 (8) | 0.9283 (3) | 0.039 (3) | |
H12C | 0.5492 | 0.7969 | 0.9246 | 0.046* | |
C13C | 0.672 (2) | 0.9168 (9) | 0.9216 (4) | 0.051 (4) | |
H13C | 0.5675 | 0.9466 | 0.9134 | 0.062* | |
C14C | 0.833 (3) | 0.9609 (9) | 0.9269 (3) | 0.060 (5) | |
H14C | 0.8394 | 1.0217 | 0.9226 | 0.071* | |
C15C | 0.988 (3) | 0.9181 (10) | 0.9387 (3) | 0.056 (4) | |
H15C | 1.1003 | 0.9490 | 0.9421 | 0.067* | |
C16C | 0.975 (2) | 0.8294 (9) | 0.9453 (3) | 0.043 (3) | |
H16C | 1.0800 | 0.7998 | 0.9535 | 0.051* | |
C10C | 0.7561 (16) | 0.6236 (7) | 0.9291 (2) | 0.026 (2) | |
C17C | 0.7538 (19) | 0.6256 (7) | 0.8963 (2) | 0.030 (3) | |
C18C | 0.588 (2) | 0.6130 (8) | 0.8815 (3) | 0.034 (3) | |
H18C | 0.4723 | 0.6021 | 0.8922 | 0.041* | |
C19C | 0.592 (2) | 0.6164 (8) | 0.8508 (3) | 0.040 (3) | |
H19C | 0.4790 | 0.6083 | 0.8407 | 0.048* | |
C20C | 0.760 (2) | 0.6317 (8) | 0.8349 (3) | 0.040 (3) | |
H20C | 0.7621 | 0.6332 | 0.8140 | 0.047* | |
C21C | 0.925 (2) | 0.6448 (8) | 0.8497 (3) | 0.038 (3) | |
H21C | 1.0404 | 0.6562 | 0.8391 | 0.045* | |
C22C | 0.918 (2) | 0.6409 (8) | 0.8806 (3) | 0.036 (3) | |
H22C | 1.0305 | 0.6493 | 0.8908 | 0.043* | |
N2C | 0.7387 (13) | 0.5491 (6) | 0.94676 (19) | 0.0225 (19) | |
C23C | 0.6857 (16) | 0.4633 (7) | 0.9368 (3) | 0.026 (2) | |
H23E | 0.6152 | 0.4712 | 0.9185 | 0.031* | |
H23F | 0.5994 | 0.4354 | 0.9520 | 0.031* | |
C24C | 0.8503 (18) | 0.4022 (7) | 0.9310 (2) | 0.029 (2) | |
C25C | 1.0318 (16) | 0.4336 (7) | 0.9252 (2) | 0.025 (2) | |
H25C | 1.0561 | 0.4942 | 0.9258 | 0.030* | |
C26C | 1.1783 (18) | 0.3763 (9) | 0.9186 (3) | 0.035 (3) | |
H26C | 1.3022 | 0.3978 | 0.9145 | 0.042* | |
C27C | 1.144 (2) | 0.2886 (9) | 0.9181 (3) | 0.040 (3) | |
H27C | 1.2443 | 0.2499 | 0.9137 | 0.048* | |
C28C | 0.968 (2) | 0.2565 (8) | 0.9237 (3) | 0.042 (3) | |
H28C | 0.9451 | 0.1958 | 0.9232 | 0.051* | |
C29C | 0.818 (2) | 0.3142 (8) | 0.9303 (3) | 0.034 (3) | |
H29C | 0.6942 | 0.2921 | 0.9343 | 0.040* | |
C1D | 0.818 (2) | 0.3224 (8) | 0.4247 (3) | 0.043 (3) | |
H1D | 0.6916 | 0.3022 | 0.4274 | 0.052* | |
C2D | 0.960 (3) | 0.2647 (10) | 0.4180 (4) | 0.056 (4) | |
H2D | 0.9314 | 0.2048 | 0.4165 | 0.067* | |
C3D | 1.144 (2) | 0.2925 (10) | 0.4132 (4) | 0.053 (4) | |
H3D | 1.2409 | 0.2526 | 0.4082 | 0.063* | |
C4D | 1.184 (2) | 0.3801 (9) | 0.4161 (3) | 0.041 (3) | |
H4D | 1.3100 | 0.3999 | 0.4131 | 0.049* | |
C5D | 1.043 (2) | 0.4387 (8) | 0.4230 (3) | 0.036 (3) | |
H5D | 1.0722 | 0.4984 | 0.4246 | 0.043* | |
C6D | 0.8578 (18) | 0.4105 (7) | 0.4277 (2) | 0.028 (2) | |
C7D | 0.6953 (18) | 0.4729 (7) | 0.4342 (3) | 0.030 (3) | |
H7G | 0.6274 | 0.4845 | 0.4158 | 0.036* | |
H7H | 0.6057 | 0.4443 | 0.4487 | 0.036* | |
N1D | 0.7538 (14) | 0.5558 (6) | 0.4456 (2) | 0.0248 (19) | |
C8D | 0.7812 (15) | 0.5676 (8) | 0.4746 (3) | 0.026 (2) | |
Au1D | 0.74653 (7) | 0.48120 (3) | 0.507417 (10) | 0.02840 (11) | |
Br1D | 0.70158 (19) | 0.37241 (10) | 0.54711 (3) | 0.0378 (3) | |
C9D | 0.7804 (17) | 0.6319 (7) | 0.4287 (2) | 0.025 (2) | |
C11D | 0.7668 (17) | 0.6376 (7) | 0.3962 (2) | 0.026 (2) | |
C12D | 0.9307 (19) | 0.6365 (8) | 0.3785 (3) | 0.033 (3) | |
H12D | 1.0494 | 0.6326 | 0.3874 | 0.040* | |
C13D | 0.925 (2) | 0.6409 (9) | 0.3480 (3) | 0.038 (3) | |
H13D | 1.0372 | 0.6392 | 0.3361 | 0.046* | |
C14D | 0.750 (2) | 0.6478 (8) | 0.3353 (3) | 0.039 (3) | |
H14D | 0.7436 | 0.6519 | 0.3144 | 0.046* | |
C15D | 0.585 (2) | 0.6489 (9) | 0.3525 (3) | 0.041 (3) | |
H15D | 0.4665 | 0.6528 | 0.3435 | 0.050* | |
C16D | 0.5951 (19) | 0.6442 (8) | 0.3830 (3) | 0.033 (3) | |
H16D | 0.4823 | 0.6455 | 0.3950 | 0.040* | |
C10D | 0.8214 (17) | 0.6933 (8) | 0.4479 (2) | 0.029 (2) | |
C17D | 0.852 (2) | 0.7895 (8) | 0.4429 (3) | 0.035 (3) | |
C18D | 1.024 (2) | 0.8274 (10) | 0.4463 (3) | 0.049 (4) | |
H18D | 1.1290 | 0.7929 | 0.4517 | 0.059* | |
C19D | 1.043 (3) | 0.9178 (11) | 0.4416 (4) | 0.062 (5) | |
H19D | 1.1618 | 0.9447 | 0.4441 | 0.074* | |
C20D | 0.891 (4) | 0.9669 (11) | 0.4336 (4) | 0.075 (7) | |
H20D | 0.9048 | 1.0280 | 0.4306 | 0.090* | |
C21D | 0.720 (3) | 0.9297 (9) | 0.4298 (3) | 0.065 (6) | |
H21D | 0.6166 | 0.9648 | 0.4239 | 0.077* | |
C22D | 0.696 (3) | 0.8391 (8) | 0.4346 (3) | 0.046 (4) | |
H22D | 0.5773 | 0.8125 | 0.4322 | 0.055* | |
N2D | 0.8220 (15) | 0.6538 (6) | 0.4757 (2) | 0.030 (2) | |
C23D | 0.8654 (19) | 0.6967 (8) | 0.5030 (2) | 0.033 (3) | |
H23G | 0.9917 | 0.7238 | 0.5006 | 0.039* | |
H23H | 0.8693 | 0.6526 | 0.5194 | 0.039* | |
C24D | 0.7224 (18) | 0.7653 (8) | 0.5107 (2) | 0.032 (3) | |
C25D | 0.778 (3) | 0.8494 (9) | 0.5159 (3) | 0.051 (4) | |
H25D | 0.9087 | 0.8637 | 0.5152 | 0.062* | |
C26D | 0.645 (3) | 0.9131 (11) | 0.5222 (4) | 0.069 (6) | |
H26D | 0.6843 | 0.9706 | 0.5257 | 0.082* | |
C27D | 0.454 (3) | 0.8929 (11) | 0.5233 (4) | 0.066 (5) | |
H27D | 0.3628 | 0.9363 | 0.5276 | 0.079* | |
C28D | 0.398 (2) | 0.8103 (11) | 0.5180 (4) | 0.056 (4) | |
H28D | 0.2678 | 0.7961 | 0.5185 | 0.067* | |
C29D | 0.532 (2) | 0.7470 (8) | 0.5120 (3) | 0.042 (3) | |
H29D | 0.4921 | 0.6895 | 0.5087 | 0.050* | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
C1A | 0.035 (7) | 0.028 (6) | 0.028 (6) | −0.003 (5) | −0.006 (5) | 0.000 (5) |
C2A | 0.061 (9) | 0.035 (7) | 0.022 (6) | −0.011 (6) | 0.000 (6) | 0.000 (5) |
C3A | 0.062 (9) | 0.027 (6) | 0.026 (6) | −0.004 (6) | 0.012 (6) | −0.004 (5) |
C4A | 0.046 (8) | 0.021 (6) | 0.043 (7) | −0.004 (5) | 0.008 (6) | −0.001 (5) |
C5A | 0.055 (8) | 0.022 (6) | 0.023 (6) | 0.008 (5) | 0.004 (5) | 0.001 (4) |
C6A | 0.035 (6) | 0.010 (4) | 0.032 (6) | 0.000 (4) | −0.007 (5) | −0.007 (4) |
C7A | 0.021 (5) | 0.022 (5) | 0.028 (6) | 0.003 (4) | 0.000 (4) | −0.003 (4) |
N1A | 0.027 (5) | 0.023 (4) | 0.020 (4) | 0.006 (4) | −0.001 (4) | −0.005 (3) |
C8A | 0.017 (5) | 0.016 (5) | 0.027 (5) | −0.001 (4) | 0.001 (4) | −0.007 (4) |
Au1A | 0.0293 (2) | 0.0163 (2) | 0.0264 (2) | 0.00075 (17) | 0.00005 (17) | −0.00331 (16) |
Br1A | 0.0273 (6) | 0.0182 (5) | 0.0382 (6) | −0.0004 (4) | 0.0008 (5) | −0.0058 (4) |
C9A | 0.043 (7) | 0.015 (5) | 0.022 (5) | −0.010 (5) | 0.003 (5) | −0.006 (4) |
C11A | 0.038 (7) | 0.025 (6) | 0.016 (5) | 0.005 (5) | −0.003 (4) | 0.000 (4) |
C12A | 0.041 (8) | 0.024 (6) | 0.041 (7) | 0.008 (5) | 0.014 (6) | 0.002 (5) |
C13A | 0.045 (8) | 0.024 (6) | 0.044 (8) | 0.001 (5) | 0.008 (6) | 0.007 (5) |
C14A | 0.059 (9) | 0.026 (6) | 0.021 (6) | 0.000 (6) | −0.004 (5) | 0.002 (4) |
C15A | 0.047 (8) | 0.024 (6) | 0.035 (7) | 0.007 (5) | −0.003 (6) | 0.002 (5) |
C16A | 0.043 (7) | 0.025 (6) | 0.031 (6) | 0.001 (5) | −0.005 (5) | 0.004 (5) |
C10A | 0.027 (6) | 0.016 (5) | 0.027 (6) | 0.002 (4) | 0.002 (4) | −0.004 (4) |
C17A | 0.074 (10) | 0.020 (6) | 0.021 (6) | −0.013 (6) | −0.004 (6) | 0.003 (4) |
C18A | 0.090 (13) | 0.062 (10) | 0.027 (7) | −0.033 (9) | 0.006 (8) | −0.010 (7) |
C19A | 0.14 (2) | 0.076 (13) | 0.030 (8) | −0.064 (14) | 0.001 (10) | −0.005 (8) |
C20A | 0.18 (2) | 0.035 (8) | 0.026 (8) | −0.020 (11) | −0.009 (12) | −0.005 (6) |
C21A | 0.16 (2) | 0.040 (9) | 0.031 (8) | 0.039 (11) | −0.022 (11) | −0.012 (7) |
C22A | 0.103 (14) | 0.043 (8) | 0.033 (8) | 0.042 (9) | −0.022 (8) | −0.017 (6) |
N2A | 0.035 (5) | 0.013 (4) | 0.025 (5) | −0.008 (4) | −0.004 (4) | −0.003 (3) |
C23A | 0.038 (7) | 0.024 (5) | 0.024 (6) | 0.002 (5) | 0.001 (5) | 0.000 (4) |
C24A | 0.043 (7) | 0.022 (5) | 0.027 (6) | 0.005 (5) | −0.007 (5) | −0.001 (4) |
C25A | 0.043 (8) | 0.032 (7) | 0.038 (7) | −0.008 (6) | 0.007 (6) | 0.003 (5) |
C26A | 0.042 (8) | 0.040 (8) | 0.055 (9) | −0.001 (6) | 0.009 (7) | 0.001 (6) |
C27A | 0.069 (11) | 0.033 (7) | 0.037 (8) | 0.009 (7) | 0.020 (7) | 0.005 (6) |
C28A | 0.073 (11) | 0.040 (8) | 0.029 (7) | 0.015 (7) | 0.007 (7) | 0.000 (6) |
C29A | 0.056 (9) | 0.031 (6) | 0.025 (6) | 0.004 (6) | −0.006 (6) | 0.000 (5) |
C1B | 0.041 (7) | 0.022 (5) | 0.027 (6) | 0.003 (5) | −0.009 (5) | −0.002 (4) |
C2B | 0.035 (7) | 0.029 (6) | 0.044 (7) | −0.002 (5) | −0.001 (6) | −0.001 (5) |
C3B | 0.042 (8) | 0.034 (7) | 0.042 (8) | 0.007 (6) | 0.008 (6) | 0.001 (5) |
C4B | 0.060 (10) | 0.042 (8) | 0.033 (7) | −0.005 (7) | 0.004 (6) | −0.011 (6) |
C5B | 0.046 (8) | 0.028 (6) | 0.030 (6) | −0.002 (5) | −0.005 (5) | −0.005 (5) |
C6B | 0.043 (7) | 0.018 (5) | 0.024 (6) | 0.004 (5) | −0.005 (5) | 0.002 (4) |
C7B | 0.040 (7) | 0.017 (5) | 0.026 (6) | 0.005 (5) | −0.007 (5) | 0.001 (4) |
N1B | 0.042 (6) | 0.019 (4) | 0.023 (5) | 0.003 (4) | −0.006 (4) | −0.002 (4) |
C8B | 0.035 (6) | 0.022 (5) | 0.020 (5) | 0.009 (4) | −0.003 (4) | −0.008 (4) |
Au1B | 0.0284 (2) | 0.0167 (2) | 0.0259 (2) | 0.00010 (16) | −0.00121 (17) | −0.00330 (16) |
Br1B | 0.0186 (5) | 0.0169 (5) | 0.0345 (6) | −0.0001 (4) | 0.0005 (4) | −0.0041 (4) |
C9B | 0.043 (7) | 0.016 (5) | 0.022 (5) | −0.001 (5) | −0.004 (5) | −0.001 (4) |
C11B | 0.071 (10) | 0.015 (5) | 0.021 (6) | −0.005 (5) | −0.008 (6) | 0.000 (4) |
C12B | 0.068 (10) | 0.032 (7) | 0.022 (6) | −0.016 (6) | −0.003 (6) | 0.003 (5) |
C13B | 0.091 (13) | 0.045 (8) | 0.024 (7) | −0.033 (8) | −0.007 (7) | 0.000 (6) |
C14B | 0.137 (18) | 0.020 (6) | 0.028 (7) | −0.015 (8) | −0.011 (9) | −0.004 (5) |
C15B | 0.128 (17) | 0.033 (8) | 0.038 (8) | 0.026 (9) | −0.023 (10) | −0.005 (6) |
C16B | 0.082 (11) | 0.026 (6) | 0.031 (7) | 0.013 (7) | −0.013 (7) | −0.007 (5) |
C10B | 0.026 (6) | 0.023 (5) | 0.033 (6) | 0.017 (4) | 0.001 (5) | −0.005 (4) |
C17B | 0.050 (8) | 0.013 (5) | 0.023 (5) | 0.000 (5) | 0.002 (5) | −0.006 (4) |
C18B | 0.046 (8) | 0.019 (5) | 0.036 (7) | 0.005 (5) | −0.013 (6) | 0.001 (5) |
C19B | 0.068 (10) | 0.024 (6) | 0.032 (7) | 0.007 (6) | −0.007 (6) | 0.002 (5) |
C20B | 0.067 (10) | 0.021 (6) | 0.025 (6) | 0.001 (6) | −0.003 (6) | 0.002 (4) |
C21B | 0.059 (9) | 0.024 (6) | 0.035 (7) | −0.004 (6) | 0.006 (6) | 0.000 (5) |
C22B | 0.045 (8) | 0.021 (6) | 0.036 (7) | −0.001 (5) | −0.005 (5) | −0.001 (5) |
N2B | 0.038 (6) | 0.021 (4) | 0.018 (4) | 0.000 (4) | −0.003 (4) | −0.002 (3) |
C23B | 0.054 (8) | 0.020 (5) | 0.025 (6) | −0.001 (5) | −0.012 (5) | −0.001 (4) |
C24B | 0.054 (8) | 0.022 (6) | 0.020 (6) | −0.006 (5) | −0.002 (5) | 0.001 (4) |
C25B | 0.072 (12) | 0.058 (10) | 0.031 (7) | −0.016 (8) | −0.006 (7) | −0.005 (6) |
C26B | 0.099 (15) | 0.055 (10) | 0.024 (7) | −0.020 (9) | 0.004 (8) | −0.007 (6) |
C27B | 0.085 (14) | 0.043 (9) | 0.047 (9) | −0.007 (8) | 0.016 (9) | −0.003 (7) |
C28B | 0.075 (11) | 0.034 (7) | 0.041 (8) | 0.012 (7) | 0.015 (7) | 0.009 (6) |
C29B | 0.056 (9) | 0.038 (7) | 0.033 (7) | 0.009 (6) | −0.001 (6) | 0.008 (6) |
C1C | 0.026 (6) | 0.023 (6) | 0.050 (8) | 0.002 (5) | 0.010 (5) | −0.011 (5) |
C2C | 0.038 (8) | 0.043 (8) | 0.060 (9) | 0.006 (6) | 0.010 (7) | −0.012 (7) |
C3C | 0.053 (9) | 0.035 (7) | 0.045 (8) | 0.015 (6) | −0.006 (7) | −0.010 (6) |
C4C | 0.068 (11) | 0.036 (8) | 0.076 (12) | 0.013 (7) | −0.025 (9) | −0.029 (8) |
C5C | 0.049 (9) | 0.028 (6) | 0.058 (9) | −0.002 (6) | −0.022 (7) | −0.013 (6) |
C6C | 0.030 (6) | 0.028 (6) | 0.020 (5) | 0.006 (5) | −0.004 (4) | −0.001 (4) |
C7C | 0.033 (6) | 0.031 (6) | 0.019 (5) | 0.005 (5) | −0.008 (4) | −0.004 (4) |
N1C | 0.033 (5) | 0.018 (4) | 0.020 (4) | 0.002 (4) | −0.008 (4) | −0.003 (3) |
C8C | 0.003 (4) | 0.014 (4) | 0.033 (6) | −0.002 (3) | −0.005 (4) | −0.005 (4) |
Au1C | 0.0233 (2) | 0.0203 (2) | 0.0244 (2) | 0.00140 (17) | −0.00110 (17) | 0.00043 (16) |
Br1C | 0.0260 (6) | 0.0347 (6) | 0.0295 (6) | −0.0004 (5) | −0.0018 (5) | 0.0035 (5) |
C9C | 0.028 (6) | 0.018 (5) | 0.028 (6) | 0.008 (4) | 0.005 (4) | −0.001 (4) |
C11C | 0.040 (7) | 0.018 (5) | 0.023 (6) | 0.000 (5) | 0.001 (5) | −0.004 (4) |
C12C | 0.042 (8) | 0.029 (6) | 0.044 (8) | 0.007 (5) | 0.010 (6) | 0.003 (5) |
C13C | 0.067 (11) | 0.027 (7) | 0.058 (10) | 0.017 (7) | 0.019 (8) | 0.006 (6) |
C14C | 0.115 (16) | 0.021 (6) | 0.040 (8) | 0.001 (8) | 0.027 (9) | −0.003 (6) |
C15C | 0.091 (13) | 0.033 (8) | 0.044 (9) | −0.024 (8) | 0.000 (8) | −0.011 (6) |
C16C | 0.068 (10) | 0.033 (7) | 0.027 (6) | −0.012 (6) | −0.008 (6) | 0.002 (5) |
C10C | 0.026 (6) | 0.025 (5) | 0.026 (6) | −0.001 (4) | −0.004 (4) | −0.001 (4) |
C17C | 0.047 (8) | 0.020 (5) | 0.022 (6) | 0.010 (5) | −0.006 (5) | −0.002 (4) |
C18C | 0.044 (8) | 0.029 (6) | 0.031 (6) | 0.011 (5) | −0.007 (5) | −0.006 (5) |
C19C | 0.059 (9) | 0.032 (7) | 0.032 (7) | 0.012 (6) | −0.015 (6) | −0.011 (5) |
C20C | 0.067 (10) | 0.029 (6) | 0.024 (6) | 0.007 (6) | −0.006 (6) | −0.002 (5) |
C21C | 0.056 (9) | 0.027 (6) | 0.029 (6) | −0.002 (6) | 0.005 (6) | −0.001 (5) |
C22C | 0.055 (9) | 0.026 (6) | 0.025 (6) | −0.001 (6) | −0.001 (6) | 0.000 (5) |
N2C | 0.029 (5) | 0.018 (4) | 0.020 (4) | 0.006 (4) | −0.002 (4) | 0.000 (3) |
C23C | 0.021 (6) | 0.021 (5) | 0.036 (6) | 0.004 (4) | −0.005 (5) | −0.001 (4) |
C24C | 0.041 (7) | 0.026 (6) | 0.021 (5) | 0.000 (5) | −0.008 (5) | 0.003 (4) |
C25C | 0.026 (6) | 0.023 (5) | 0.028 (6) | 0.003 (4) | −0.008 (4) | −0.002 (4) |
C26C | 0.028 (7) | 0.048 (8) | 0.029 (6) | 0.002 (5) | −0.002 (5) | −0.005 (5) |
C27C | 0.046 (8) | 0.035 (7) | 0.039 (7) | 0.016 (6) | −0.006 (6) | −0.016 (5) |
C28C | 0.058 (9) | 0.024 (6) | 0.045 (8) | 0.010 (6) | −0.010 (7) | −0.006 (5) |
C29C | 0.046 (8) | 0.023 (6) | 0.033 (6) | −0.001 (5) | −0.005 (5) | −0.001 (5) |
C1D | 0.046 (8) | 0.027 (6) | 0.057 (9) | 0.001 (6) | −0.011 (7) | −0.003 (6) |
C2D | 0.071 (12) | 0.029 (7) | 0.070 (11) | 0.010 (7) | −0.020 (9) | −0.015 (7) |
C3D | 0.061 (11) | 0.046 (8) | 0.053 (9) | 0.024 (8) | −0.010 (8) | −0.020 (7) |
C4D | 0.040 (8) | 0.046 (8) | 0.038 (7) | 0.009 (6) | −0.009 (6) | −0.009 (6) |
C5D | 0.045 (8) | 0.032 (6) | 0.030 (6) | 0.007 (6) | −0.002 (5) | −0.005 (5) |
C6D | 0.039 (7) | 0.023 (5) | 0.022 (5) | 0.004 (5) | −0.003 (5) | −0.002 (4) |
C7D | 0.045 (7) | 0.025 (6) | 0.021 (5) | −0.006 (5) | −0.002 (5) | 0.002 (4) |
N1D | 0.031 (5) | 0.022 (4) | 0.021 (5) | 0.004 (4) | −0.001 (4) | −0.001 (3) |
C8D | 0.011 (5) | 0.037 (6) | 0.030 (6) | 0.012 (4) | −0.005 (4) | −0.007 (5) |
Au1D | 0.0335 (3) | 0.0281 (2) | 0.0234 (2) | 0.00435 (19) | −0.00027 (19) | 0.00187 (18) |
Br1D | 0.0332 (7) | 0.0502 (8) | 0.0291 (6) | 0.0015 (6) | 0.0015 (5) | 0.0060 (5) |
C9D | 0.036 (6) | 0.016 (5) | 0.023 (5) | 0.003 (4) | 0.004 (4) | −0.002 (4) |
C11D | 0.039 (7) | 0.016 (5) | 0.025 (6) | 0.001 (4) | −0.002 (5) | −0.001 (4) |
C12D | 0.035 (7) | 0.033 (6) | 0.032 (6) | 0.003 (5) | −0.003 (5) | −0.004 (5) |
C13D | 0.051 (9) | 0.038 (7) | 0.026 (6) | 0.001 (6) | 0.003 (6) | −0.006 (5) |
C14D | 0.066 (10) | 0.025 (6) | 0.024 (6) | 0.005 (6) | −0.004 (6) | −0.004 (5) |
C15D | 0.047 (8) | 0.046 (8) | 0.030 (7) | 0.002 (6) | −0.002 (6) | 0.000 (6) |
C16D | 0.040 (7) | 0.032 (6) | 0.029 (6) | 0.003 (5) | −0.003 (5) | −0.003 (5) |
C10D | 0.029 (6) | 0.037 (6) | 0.021 (5) | 0.005 (5) | −0.010 (4) | −0.004 (5) |
C17D | 0.059 (9) | 0.030 (6) | 0.017 (5) | −0.001 (6) | 0.001 (5) | −0.004 (4) |
C18D | 0.066 (11) | 0.046 (8) | 0.036 (8) | −0.013 (7) | −0.006 (7) | −0.005 (6) |
C19D | 0.102 (15) | 0.040 (9) | 0.044 (9) | −0.028 (9) | 0.003 (9) | −0.005 (7) |
C20D | 0.15 (2) | 0.027 (8) | 0.045 (10) | −0.017 (11) | 0.024 (11) | −0.016 (7) |
C21D | 0.136 (18) | 0.024 (7) | 0.033 (8) | 0.018 (9) | 0.014 (9) | −0.003 (6) |
C22D | 0.085 (12) | 0.023 (6) | 0.029 (7) | 0.007 (7) | 0.001 (7) | −0.003 (5) |
N2D | 0.036 (6) | 0.029 (5) | 0.025 (5) | 0.005 (4) | 0.001 (4) | −0.004 (4) |
C23D | 0.046 (8) | 0.037 (7) | 0.016 (5) | 0.004 (5) | −0.012 (5) | −0.003 (5) |
C24D | 0.038 (7) | 0.041 (7) | 0.017 (5) | 0.001 (5) | 0.001 (5) | −0.001 (5) |
C25D | 0.069 (11) | 0.038 (8) | 0.050 (9) | 0.005 (7) | −0.021 (8) | −0.016 (6) |
C26D | 0.097 (16) | 0.045 (9) | 0.067 (12) | 0.013 (9) | −0.026 (11) | −0.031 (8) |
C27D | 0.097 (15) | 0.047 (9) | 0.055 (10) | 0.033 (10) | −0.016 (10) | −0.023 (8) |
C28D | 0.053 (10) | 0.068 (11) | 0.049 (9) | 0.014 (8) | −0.001 (7) | −0.016 (8) |
C29D | 0.060 (9) | 0.027 (6) | 0.038 (7) | 0.009 (6) | 0.008 (6) | −0.009 (5) |
Geometric parameters (Å, º) top
C1A—C2A | 1.385 (18) | C1C—C6C | 1.375 (17) |
C1A—C6A | 1.412 (16) | C1C—C2C | 1.394 (17) |
C1A—H1A | 0.9500 | C1C—H1C | 0.9500 |
C2A—C3A | 1.39 (2) | C2C—C3C | 1.38 (2) |
C2A—H2A | 0.9500 | C2C—H2C | 0.9500 |
C3A—C4A | 1.387 (19) | C3C—C4C | 1.37 (2) |
C3A—H3A | 0.9500 | C3C—H3C | 0.9500 |
C4A—C5A | 1.340 (18) | C4C—C5C | 1.39 (2) |
C4A—H4A | 0.9500 | C4C—H4C | 0.9500 |
C5A—C6A | 1.430 (18) | C5C—C6C | 1.394 (17) |
C5A—H5A | 0.9500 | C5C—H5C | 0.9500 |
C6A—C7A | 1.481 (16) | C6C—C7C | 1.497 (16) |
C7A—N1A | 1.466 (14) | C7C—N1C | 1.460 (13) |
C7A—H7A | 0.9900 | C7C—H7E | 0.9900 |
C7A—H7B | 0.9900 | C7C—H7F | 0.9900 |
N1A—C8A | 1.354 (14) | N1C—C8C | 1.328 (13) |
N1A—C9A | 1.404 (13) | N1C—C9C | 1.385 (14) |
C8A—N2A | 1.356 (13) | C8C—N2C | 1.339 (13) |
C8A—Au1A | 1.997 (10) | C8C—Au1C | 2.016 (10) |
Au1A—Br1A | 2.4796 (12) | Au1C—Br1C | 2.4354 (13) |
C9A—C10A | 1.349 (16) | C9C—C10C | 1.341 (15) |
C9A—C11A | 1.491 (15) | C9C—C11C | 1.486 (15) |
C11A—C16A | 1.384 (17) | C11C—C16C | 1.385 (19) |
C11A—C12A | 1.387 (18) | C11C—C12C | 1.390 (18) |
C12A—C13A | 1.387 (16) | C12C—C13C | 1.396 (18) |
C12A—H12A | 0.9500 | C12C—H12C | 0.9500 |
C13A—C14A | 1.365 (19) | C13C—C14C | 1.36 (3) |
C13A—H13A | 0.9500 | C13C—H13C | 0.9500 |
C14A—C15A | 1.389 (19) | C14C—C15C | 1.40 (3) |
C14A—H14A | 0.9500 | C14C—H14C | 0.9500 |
C15A—C16A | 1.394 (16) | C15C—C16C | 1.389 (19) |
C15A—H15A | 0.9500 | C15C—H15C | 0.9500 |
C16A—H16A | 0.9500 | C16C—H16C | 0.9500 |
C10A—N2A | 1.377 (13) | C10C—N2C | 1.379 (14) |
C10A—C17A | 1.491 (15) | C10C—C17C | 1.487 (15) |
C17A—C22A | 1.37 (2) | C17C—C22C | 1.360 (19) |
C17A—C18A | 1.39 (2) | C17C—C18C | 1.398 (18) |
C18A—C19A | 1.42 (2) | C18C—C19C | 1.391 (18) |
C18A—H18A | 0.9500 | C18C—H18C | 0.9500 |
C19A—C20A | 1.38 (3) | C19C—C20C | 1.39 (2) |
C19A—H19A | 0.9500 | C19C—H19C | 0.9500 |
C20A—C21A | 1.36 (3) | C20C—C21C | 1.39 (2) |
C20A—H20A | 0.9500 | C20C—H20C | 0.9500 |
C21A—C22A | 1.40 (2) | C21C—C22C | 1.401 (17) |
C21A—H21A | 0.9500 | C21C—H21C | 0.9500 |
C22A—H22A | 0.9500 | C22C—H22C | 0.9500 |
N2A—C23A | 1.470 (14) | N2C—C23C | 1.466 (14) |
C23A—C24A | 1.520 (17) | C23C—C24C | 1.519 (16) |
C23A—H23A | 0.9900 | C23C—H23E | 0.9900 |
C23A—H23B | 0.9900 | C23C—H23F | 0.9900 |
C24A—C29A | 1.376 (17) | C24C—C29C | 1.376 (16) |
C24A—C25A | 1.394 (19) | C24C—C25C | 1.390 (17) |
C25A—C26A | 1.389 (19) | C25C—C26C | 1.393 (17) |
C25A—H25A | 0.9500 | C25C—H25C | 0.9500 |
C26A—C27A | 1.38 (2) | C26C—C27C | 1.374 (19) |
C26A—H26A | 0.9500 | C26C—H26C | 0.9500 |
C27A—C28A | 1.37 (2) | C27C—C28C | 1.36 (2) |
C27A—H27A | 0.9500 | C27C—H27C | 0.9500 |
C28A—C29A | 1.39 (2) | C28C—C29C | 1.414 (19) |
C28A—H28A | 0.9500 | C28C—H28C | 0.9500 |
C29A—H29A | 0.9500 | C29C—H29C | 0.9500 |
C1B—C2B | 1.384 (18) | C1D—C2D | 1.38 (2) |
C1B—C6B | 1.397 (17) | C1D—C6D | 1.399 (17) |
C1B—H1B | 0.9500 | C1D—H1D | 0.9500 |
C2B—C3B | 1.371 (19) | C2D—C3D | 1.38 (2) |
C2B—H2B | 0.9500 | C2D—H2D | 0.9500 |
C3B—C4B | 1.38 (2) | C3D—C4D | 1.39 (2) |
C3B—H3B | 0.9500 | C3D—H3D | 0.9500 |
C4B—C5B | 1.383 (19) | C4D—C5D | 1.383 (18) |
C4B—H4B | 0.9500 | C4D—H4D | 0.9500 |
C5B—C6B | 1.395 (16) | C5D—C6D | 1.390 (19) |
C5B—H5B | 0.9500 | C5D—H5D | 0.9500 |
C6B—C7B | 1.508 (17) | C6D—C7D | 1.526 (17) |
C7B—N1B | 1.463 (14) | C7D—N1D | 1.462 (14) |
C7B—H7C | 0.9900 | C7D—H7G | 0.9900 |
C7B—H7D | 0.9900 | C7D—H7H | 0.9900 |
N1B—C8B | 1.328 (14) | N1D—C8D | 1.359 (14) |
N1B—C9B | 1.386 (14) | N1D—C9D | 1.386 (14) |
C8B—N2B | 1.345 (14) | C8D—N2D | 1.361 (15) |
C8B—Au1B | 2.013 (11) | C8D—Au1D | 1.969 (12) |
Au1B—Br1B | 2.4789 (11) | Au1D—Br1D | 2.4279 (14) |
C9B—C10B | 1.343 (16) | C9D—C10D | 1.350 (16) |
C9B—C11B | 1.476 (15) | C9D—C11D | 1.482 (15) |
C11B—C12B | 1.39 (2) | C11D—C16D | 1.379 (17) |
C11B—C16B | 1.40 (2) | C11D—C12D | 1.391 (17) |
C12B—C13B | 1.386 (19) | C12D—C13D | 1.386 (17) |
C12B—H12B | 0.9500 | C12D—H12D | 0.9500 |
C13B—C14B | 1.37 (3) | C13D—C14D | 1.39 (2) |
C13B—H13B | 0.9500 | C13D—H13D | 0.9500 |
C14B—C15B | 1.38 (3) | C14D—C15D | 1.38 (2) |
C14B—H14B | 0.9500 | C14D—H14D | 0.9500 |
C15B—C16B | 1.395 (19) | C15D—C16D | 1.392 (18) |
C15B—H15B | 0.9500 | C15D—H15D | 0.9500 |
C16B—H16B | 0.9500 | C16D—H16D | 0.9500 |
C10B—N2B | 1.391 (14) | C10D—N2D | 1.382 (15) |
C10B—C17B | 1.492 (15) | C10D—C17D | 1.504 (17) |
C17B—C18B | 1.385 (17) | C17D—C18D | 1.37 (2) |
C17B—C22B | 1.385 (18) | C17D—C22D | 1.40 (2) |
C18B—C19B | 1.405 (16) | C18D—C19D | 1.40 (2) |
C18B—H18B | 0.9500 | C18D—H18D | 0.9500 |
C19B—C20B | 1.37 (2) | C19D—C20D | 1.37 (3) |
C19B—H19B | 0.9500 | C19D—H19D | 0.9500 |
C20B—C21B | 1.38 (2) | C20D—C21D | 1.36 (3) |
C20B—H20B | 0.9500 | C20D—H20D | 0.9500 |
C21B—C22B | 1.396 (17) | C21D—C22D | 1.415 (19) |
C21B—H21B | 0.9500 | C21D—H21D | 0.9500 |
C22B—H22B | 0.9500 | C22D—H22D | 0.9500 |
N2B—C23B | 1.458 (14) | N2D—C23D | 1.467 (14) |
C23B—C24B | 1.501 (18) | C23D—C24D | 1.506 (18) |
C23B—H23C | 0.9900 | C23D—H23G | 0.9900 |
C23B—H23D | 0.9900 | C23D—H23H | 0.9900 |
C24B—C29B | 1.33 (2) | C24D—C29D | 1.38 (2) |
C24B—C25B | 1.402 (18) | C24D—C25D | 1.386 (19) |
C25B—C26B | 1.42 (2) | C25D—C26D | 1.39 (2) |
C25B—H25B | 0.9500 | C25D—H25D | 0.9500 |
C26B—C27B | 1.34 (3) | C26D—C27D | 1.39 (3) |
C26B—H26B | 0.9500 | C26D—H26D | 0.9500 |
C27B—C28B | 1.36 (2) | C27D—C28D | 1.37 (2) |
C27B—H27B | 0.9500 | C27D—H27D | 0.9500 |
C28B—C29B | 1.44 (2) | C28D—C29D | 1.39 (2) |
C28B—H28B | 0.9500 | C28D—H28D | 0.9500 |
C29B—H29B | 0.9500 | C29D—H29D | 0.9500 |
| | | |
C2A—C1A—C6A | 121.0 (12) | C6C—C1C—C2C | 121.9 (12) |
C2A—C1A—H1A | 119.5 | C6C—C1C—H1C | 119.0 |
C6A—C1A—H1A | 119.5 | C2C—C1C—H1C | 119.0 |
C1A—C2A—C3A | 120.0 (12) | C3C—C2C—C1C | 119.2 (14) |
C1A—C2A—H2A | 120.0 | C3C—C2C—H2C | 120.4 |
C3A—C2A—H2A | 120.0 | C1C—C2C—H2C | 120.4 |
C4A—C3A—C2A | 120.2 (12) | C4C—C3C—C2C | 119.6 (13) |
C4A—C3A—H3A | 119.9 | C4C—C3C—H3C | 120.2 |
C2A—C3A—H3A | 119.9 | C2C—C3C—H3C | 120.2 |
C5A—C4A—C3A | 120.0 (14) | C3C—C4C—C5C | 120.8 (14) |
C5A—C4A—H4A | 120.0 | C3C—C4C—H4C | 119.6 |
C3A—C4A—H4A | 120.0 | C5C—C4C—H4C | 119.6 |
C4A—C5A—C6A | 122.7 (12) | C4C—C5C—C6C | 120.3 (14) |
C4A—C5A—H5A | 118.6 | C4C—C5C—H5C | 119.8 |
C6A—C5A—H5A | 118.6 | C6C—C5C—H5C | 119.8 |
C1A—C6A—C5A | 116.1 (11) | C1C—C6C—C5C | 118.1 (11) |
C1A—C6A—C7A | 118.6 (11) | C1C—C6C—C7C | 121.2 (11) |
C5A—C6A—C7A | 125.2 (10) | C5C—C6C—C7C | 120.7 (12) |
N1A—C7A—C6A | 115.4 (9) | N1C—C7C—C6C | 113.5 (9) |
N1A—C7A—H7A | 108.4 | N1C—C7C—H7E | 108.9 |
C6A—C7A—H7A | 108.4 | C6C—C7C—H7E | 108.9 |
N1A—C7A—H7B | 108.4 | N1C—C7C—H7F | 108.9 |
C6A—C7A—H7B | 108.4 | C6C—C7C—H7F | 108.9 |
H7A—C7A—H7B | 107.5 | H7E—C7C—H7F | 107.7 |
C8A—N1A—C9A | 109.9 (9) | C8C—N1C—C9C | 109.8 (9) |
C8A—N1A—C7A | 124.3 (9) | C8C—N1C—C7C | 123.9 (9) |
C9A—N1A—C7A | 125.2 (9) | C9C—N1C—C7C | 126.3 (9) |
N1A—C8A—N2A | 105.5 (8) | N1C—C8C—N2C | 106.6 (9) |
N1A—C8A—Au1A | 125.7 (8) | N1C—C8C—Au1C | 128.8 (8) |
N2A—C8A—Au1A | 128.8 (8) | N2C—C8C—Au1C | 124.5 (7) |
C8A—Au1A—Br1A | 178.7 (3) | C8C—Au1C—Br1C | 178.2 (3) |
C10A—C9A—N1A | 106.6 (9) | C10C—C9C—N1C | 106.9 (9) |
C10A—C9A—C11A | 129.8 (10) | C10C—C9C—C11C | 130.3 (11) |
N1A—C9A—C11A | 123.5 (10) | N1C—C9C—C11C | 122.7 (10) |
C16A—C11A—C12A | 120.4 (11) | C16C—C11C—C12C | 118.6 (12) |
C16A—C11A—C9A | 121.7 (11) | C16C—C11C—C9C | 123.4 (11) |
C12A—C11A—C9A | 117.9 (11) | C12C—C11C—C9C | 118.0 (11) |
C11A—C12A—C13A | 119.5 (12) | C11C—C12C—C13C | 120.8 (14) |
C11A—C12A—H12A | 120.3 | C11C—C12C—H12C | 119.6 |
C13A—C12A—H12A | 120.3 | C13C—C12C—H12C | 119.6 |
C14A—C13A—C12A | 120.1 (13) | C14C—C13C—C12C | 119.5 (15) |
C14A—C13A—H13A | 119.9 | C14C—C13C—H13C | 120.3 |
C12A—C13A—H13A | 119.9 | C12C—C13C—H13C | 120.3 |
C13A—C14A—C15A | 121.1 (12) | C13C—C14C—C15C | 121.0 (13) |
C13A—C14A—H14A | 119.4 | C13C—C14C—H14C | 119.5 |
C15A—C14A—H14A | 119.4 | C15C—C14C—H14C | 119.5 |
C14A—C15A—C16A | 119.0 (12) | C16C—C15C—C14C | 118.8 (15) |
C14A—C15A—H15A | 120.5 | C16C—C15C—H15C | 120.6 |
C16A—C15A—H15A | 120.5 | C14C—C15C—H15C | 120.6 |
C11A—C16A—C15A | 119.8 (12) | C11C—C16C—C15C | 121.2 (15) |
C11A—C16A—H16A | 120.1 | C11C—C16C—H16C | 119.4 |
C15A—C16A—H16A | 120.1 | C15C—C16C—H16C | 119.4 |
C9A—C10A—N2A | 107.1 (9) | C9C—C10C—N2C | 106.6 (10) |
C9A—C10A—C17A | 128.2 (10) | C9C—C10C—C17C | 128.8 (11) |
N2A—C10A—C17A | 124.6 (10) | N2C—C10C—C17C | 124.3 (10) |
C22A—C17A—C18A | 120.3 (14) | C22C—C17C—C18C | 119.5 (11) |
C22A—C17A—C10A | 119.5 (13) | C22C—C17C—C10C | 118.8 (11) |
C18A—C17A—C10A | 120.2 (14) | C18C—C17C—C10C | 121.7 (12) |
C17A—C18A—C19A | 118.9 (19) | C19C—C18C—C17C | 119.7 (13) |
C17A—C18A—H18A | 120.5 | C19C—C18C—H18C | 120.2 |
C19A—C18A—H18A | 120.5 | C17C—C18C—H18C | 120.2 |
C20A—C19A—C18A | 119 (2) | C20C—C19C—C18C | 120.6 (13) |
C20A—C19A—H19A | 120.6 | C20C—C19C—H19C | 119.7 |
C18A—C19A—H19A | 120.6 | C18C—C19C—H19C | 119.7 |
C21A—C20A—C19A | 121.9 (16) | C19C—C20C—C21C | 119.7 (12) |
C21A—C20A—H20A | 119.0 | C19C—C20C—H20C | 120.1 |
C19A—C20A—H20A | 119.0 | C21C—C20C—H20C | 120.1 |
C20A—C21A—C22A | 119.4 (19) | C20C—C21C—C22C | 119.0 (13) |
C20A—C21A—H21A | 120.3 | C20C—C21C—H21C | 120.5 |
C22A—C21A—H21A | 120.3 | C22C—C21C—H21C | 120.5 |
C17A—C22A—C21A | 120.5 (18) | C17C—C22C—C21C | 121.6 (13) |
C17A—C22A—H22A | 119.8 | C17C—C22C—H22C | 119.2 |
C21A—C22A—H22A | 119.8 | C21C—C22C—H22C | 119.2 |
C8A—N2A—C10A | 110.9 (9) | C8C—N2C—C10C | 110.0 (9) |
C8A—N2A—C23A | 124.2 (9) | C8C—N2C—C23C | 124.3 (9) |
C10A—N2A—C23A | 124.8 (9) | C10C—N2C—C23C | 125.4 (9) |
N2A—C23A—C24A | 112.2 (10) | N2C—C23C—C24C | 114.8 (9) |
N2A—C23A—H23A | 109.2 | N2C—C23C—H23E | 108.6 |
C24A—C23A—H23A | 109.2 | C24C—C23C—H23E | 108.6 |
N2A—C23A—H23B | 109.2 | N2C—C23C—H23F | 108.6 |
C24A—C23A—H23B | 109.2 | C24C—C23C—H23F | 108.6 |
H23A—C23A—H23B | 107.9 | H23E—C23C—H23F | 107.6 |
C29A—C24A—C25A | 118.5 (13) | C29C—C24C—C25C | 119.2 (12) |
C29A—C24A—C23A | 120.2 (12) | C29C—C24C—C23C | 119.3 (12) |
C25A—C24A—C23A | 121.2 (11) | C25C—C24C—C23C | 121.4 (10) |
C26A—C25A—C24A | 120.0 (14) | C24C—C25C—C26C | 120.0 (11) |
C26A—C25A—H25A | 120.0 | C24C—C25C—H25C | 120.0 |
C24A—C25A—H25A | 120.0 | C26C—C25C—H25C | 120.0 |
C27A—C26A—C25A | 120.6 (15) | C27C—C26C—C25C | 120.0 (12) |
C27A—C26A—H26A | 119.7 | C27C—C26C—H26C | 120.0 |
C25A—C26A—H26A | 119.7 | C25C—C26C—H26C | 120.0 |
C28A—C27A—C26A | 119.7 (14) | C28C—C27C—C26C | 121.0 (12) |
C28A—C27A—H27A | 120.2 | C28C—C27C—H27C | 119.5 |
C26A—C27A—H27A | 120.2 | C26C—C27C—H27C | 119.5 |
C27A—C28A—C29A | 119.9 (14) | C27C—C28C—C29C | 119.5 (12) |
C27A—C28A—H28A | 120.0 | C27C—C28C—H28C | 120.3 |
C29A—C28A—H28A | 120.0 | C29C—C28C—H28C | 120.3 |
C24A—C29A—C28A | 121.3 (15) | C24C—C29C—C28C | 120.3 (13) |
C24A—C29A—H29A | 119.4 | C24C—C29C—H29C | 119.9 |
C28A—C29A—H29A | 119.4 | C28C—C29C—H29C | 119.9 |
C2B—C1B—C6B | 121.2 (11) | C2D—C1D—C6D | 120.4 (14) |
C2B—C1B—H1B | 119.4 | C2D—C1D—H1D | 119.8 |
C6B—C1B—H1B | 119.4 | C6D—C1D—H1D | 119.8 |
C3B—C2B—C1B | 119.7 (12) | C1D—C2D—C3D | 121.1 (14) |
C3B—C2B—H2B | 120.2 | C1D—C2D—H2D | 119.5 |
C1B—C2B—H2B | 120.2 | C3D—C2D—H2D | 119.5 |
C2B—C3B—C4B | 120.1 (13) | C2D—C3D—C4D | 118.7 (14) |
C2B—C3B—H3B | 119.9 | C2D—C3D—H3D | 120.7 |
C4B—C3B—H3B | 119.9 | C4D—C3D—H3D | 120.7 |
C3B—C4B—C5B | 120.8 (13) | C5D—C4D—C3D | 120.9 (15) |
C3B—C4B—H4B | 119.6 | C5D—C4D—H4D | 119.5 |
C5B—C4B—H4B | 119.6 | C3D—C4D—H4D | 119.5 |
C4B—C5B—C6B | 119.9 (13) | C4D—C5D—C6D | 120.2 (13) |
C4B—C5B—H5B | 120.1 | C4D—C5D—H5D | 119.9 |
C6B—C5B—H5B | 120.1 | C6D—C5D—H5D | 119.9 |
C5B—C6B—C1B | 118.4 (12) | C5D—C6D—C1D | 118.7 (12) |
C5B—C6B—C7B | 121.1 (11) | C5D—C6D—C7D | 122.4 (11) |
C1B—C6B—C7B | 120.5 (10) | C1D—C6D—C7D | 118.8 (12) |
N1B—C7B—C6B | 112.9 (10) | N1D—C7D—C6D | 114.1 (10) |
N1B—C7B—H7C | 109.0 | N1D—C7D—H7G | 108.7 |
C6B—C7B—H7C | 109.0 | C6D—C7D—H7G | 108.7 |
N1B—C7B—H7D | 109.0 | N1D—C7D—H7H | 108.7 |
C6B—C7B—H7D | 109.0 | C6D—C7D—H7H | 108.7 |
H7C—C7B—H7D | 107.8 | H7G—C7D—H7H | 107.6 |
C8B—N1B—C9B | 109.7 (9) | C8D—N1D—C9D | 112.0 (9) |
C8B—N1B—C7B | 125.4 (9) | C8D—N1D—C7D | 123.2 (9) |
C9B—N1B—C7B | 124.9 (9) | C9D—N1D—C7D | 124.8 (9) |
N1B—C8B—N2B | 106.9 (9) | N1D—C8D—N2D | 103.9 (10) |
N1B—C8B—Au1B | 128.7 (8) | N1D—C8D—Au1D | 127.2 (9) |
N2B—C8B—Au1B | 124.3 (8) | N2D—C8D—Au1D | 128.7 (8) |
C8B—Au1B—Br1B | 178.1 (3) | C8D—Au1D—Br1D | 178.8 (3) |
C10B—C9B—N1B | 107.4 (9) | C10D—C9D—N1D | 105.5 (10) |
C10B—C9B—C11B | 129.0 (10) | C10D—C9D—C11D | 130.7 (10) |
N1B—C9B—C11B | 123.5 (10) | N1D—C9D—C11D | 123.8 (9) |
C12B—C11B—C16B | 118.7 (12) | C16D—C11D—C12D | 119.0 (11) |
C12B—C11B—C9B | 123.3 (13) | C16D—C11D—C9D | 121.6 (11) |
C16B—C11B—C9B | 118.0 (12) | C12D—C11D—C9D | 119.4 (11) |
C13B—C12B—C11B | 120.0 (16) | C13D—C12D—C11D | 121.4 (12) |
C13B—C12B—H12B | 120.0 | C13D—C12D—H12D | 119.3 |
C11B—C12B—H12B | 120.0 | C11D—C12D—H12D | 119.3 |
C14B—C13B—C12B | 120.9 (16) | C12D—C13D—C14D | 118.5 (13) |
C14B—C13B—H13B | 119.6 | C12D—C13D—H13D | 120.8 |
C12B—C13B—H13B | 119.6 | C14D—C13D—H13D | 120.8 |
C13B—C14B—C15B | 120.4 (14) | C15D—C14D—C13D | 121.2 (12) |
C13B—C14B—H14B | 119.8 | C15D—C14D—H14D | 119.4 |
C15B—C14B—H14B | 119.8 | C13D—C14D—H14D | 119.4 |
C14B—C15B—C16B | 119.3 (18) | C14D—C15D—C16D | 119.3 (13) |
C14B—C15B—H15B | 120.4 | C14D—C15D—H15D | 120.4 |
C16B—C15B—H15B | 120.4 | C16D—C15D—H15D | 120.4 |
C15B—C16B—C11B | 120.8 (16) | C11D—C16D—C15D | 120.7 (13) |
C15B—C16B—H16B | 119.6 | C11D—C16D—H16D | 119.7 |
C11B—C16B—H16B | 119.6 | C15D—C16D—H16D | 119.7 |
C9B—C10B—N2B | 106.3 (10) | C9D—C10D—N2D | 107.7 (11) |
C9B—C10B—C17B | 128.8 (10) | C9D—C10D—C17D | 130.0 (10) |
N2B—C10B—C17B | 124.9 (10) | N2D—C10D—C17D | 122.1 (10) |
C18B—C17B—C22B | 120.3 (11) | C18D—C17D—C22D | 121.0 (13) |
C18B—C17B—C10B | 121.6 (11) | C18D—C17D—C10D | 121.9 (13) |
C22B—C17B—C10B | 118.1 (11) | C22D—C17D—C10D | 117.1 (12) |
C17B—C18B—C19B | 118.1 (13) | C17D—C18D—C19D | 119.4 (17) |
C17B—C18B—H18B | 121.0 | C17D—C18D—H18D | 120.3 |
C19B—C18B—H18B | 121.0 | C19D—C18D—H18D | 120.3 |
C20B—C19B—C18B | 121.9 (13) | C20D—C19D—C18D | 119.8 (18) |
C20B—C19B—H19B | 119.0 | C20D—C19D—H19D | 120.1 |
C18B—C19B—H19B | 119.0 | C18D—C19D—H19D | 120.1 |
C19B—C20B—C21B | 119.7 (12) | C21D—C20D—C19D | 121.3 (16) |
C19B—C20B—H20B | 120.2 | C21D—C20D—H20D | 119.4 |
C21B—C20B—H20B | 120.2 | C19D—C20D—H20D | 119.4 |
C20B—C21B—C22B | 119.4 (13) | C20D—C21D—C22D | 120.1 (18) |
C20B—C21B—H21B | 120.3 | C20D—C21D—H21D | 120.0 |
C22B—C21B—H21B | 120.3 | C22D—C21D—H21D | 120.0 |
C17B—C22B—C21B | 120.6 (13) | C17D—C22D—C21D | 118.4 (17) |
C17B—C22B—H22B | 119.7 | C17D—C22D—H22D | 120.8 |
C21B—C22B—H22B | 119.7 | C21D—C22D—H22D | 120.8 |
C8B—N2B—C10B | 109.6 (9) | C8D—N2D—C10D | 110.8 (10) |
C8B—N2B—C23B | 124.6 (9) | C8D—N2D—C23D | 123.6 (10) |
C10B—N2B—C23B | 125.6 (9) | C10D—N2D—C23D | 125.5 (10) |
N2B—C23B—C24B | 114.4 (11) | N2D—C23D—C24D | 112.2 (10) |
N2B—C23B—H23C | 108.7 | N2D—C23D—H23G | 109.2 |
C24B—C23B—H23C | 108.7 | C24D—C23D—H23G | 109.2 |
N2B—C23B—H23D | 108.7 | N2D—C23D—H23H | 109.2 |
C24B—C23B—H23D | 108.7 | C24D—C23D—H23H | 109.2 |
H23C—C23B—H23D | 107.6 | H23G—C23D—H23H | 107.9 |
C29B—C24B—C25B | 117.6 (14) | C29D—C24D—C25D | 118.2 (13) |
C29B—C24B—C23B | 122.8 (11) | C29D—C24D—C23D | 121.0 (12) |
C25B—C24B—C23B | 119.5 (13) | C25D—C24D—C23D | 120.7 (13) |
C24B—C25B—C26B | 119.8 (16) | C24D—C25D—C26D | 120.4 (17) |
C24B—C25B—H25B | 120.1 | C24D—C25D—H25D | 119.8 |
C26B—C25B—H25B | 120.1 | C26D—C25D—H25D | 119.8 |
C27B—C26B—C25B | 121.0 (15) | C27D—C26D—C25D | 120.2 (16) |
C27B—C26B—H26B | 119.5 | C27D—C26D—H26D | 119.9 |
C25B—C26B—H26B | 119.5 | C25D—C26D—H26D | 119.9 |
C26B—C27B—C28B | 120.2 (17) | C28D—C27D—C26D | 119.6 (16) |
C26B—C27B—H27B | 119.9 | C28D—C27D—H27D | 120.2 |
C28B—C27B—H27B | 119.9 | C26D—C27D—H27D | 120.2 |
C27B—C28B—C29B | 118.8 (17) | C27D—C28D—C29D | 119.8 (17) |
C27B—C28B—H28B | 120.6 | C27D—C28D—H28D | 120.1 |
C29B—C28B—H28B | 120.6 | C29D—C28D—H28D | 120.1 |
C24B—C29B—C28B | 122.5 (14) | C24D—C29D—C28D | 121.8 (14) |
C24B—C29B—H29B | 118.8 | C24D—C29D—H29D | 119.1 |
C28B—C29B—H29B | 118.8 | C28D—C29D—H29D | 119.1 |
| | | |
C6A—C1A—C2A—C3A | −0.3 (18) | C6C—C1C—C2C—C3C | −1 (2) |
C1A—C2A—C3A—C4A | 0.9 (19) | C1C—C2C—C3C—C4C | 0 (2) |
C2A—C3A—C4A—C5A | −0.4 (18) | C2C—C3C—C4C—C5C | 1 (3) |
C3A—C4A—C5A—C6A | −0.7 (18) | C3C—C4C—C5C—C6C | −2 (3) |
C2A—C1A—C6A—C5A | −0.7 (16) | C2C—C1C—C6C—C5C | 1 (2) |
C2A—C1A—C6A—C7A | 175.9 (11) | C2C—C1C—C6C—C7C | 179.9 (13) |
C4A—C5A—C6A—C1A | 1.3 (16) | C4C—C5C—C6C—C1C | 1 (2) |
C4A—C5A—C6A—C7A | −175.1 (11) | C4C—C5C—C6C—C7C | −178.3 (14) |
C1A—C6A—C7A—N1A | 167.1 (9) | C1C—C6C—C7C—N1C | 43.3 (16) |
C5A—C6A—C7A—N1A | −16.6 (15) | C5C—C6C—C7C—N1C | −137.3 (12) |
C6A—C7A—N1A—C8A | 92.5 (13) | C6C—C7C—N1C—C8C | −118.7 (12) |
C6A—C7A—N1A—C9A | −97.5 (12) | C6C—C7C—N1C—C9C | 61.6 (16) |
C9A—N1A—C8A—N2A | −0.4 (12) | C9C—N1C—C8C—N2C | 2.8 (12) |
C7A—N1A—C8A—N2A | 170.9 (9) | C7C—N1C—C8C—N2C | −176.9 (10) |
C9A—N1A—C8A—Au1A | 178.1 (8) | C9C—N1C—C8C—Au1C | 179.8 (8) |
C7A—N1A—C8A—Au1A | −10.6 (15) | C7C—N1C—C8C—Au1C | 0.1 (16) |
C8A—N1A—C9A—C10A | 1.6 (13) | C8C—N1C—C9C—C10C | −2.1 (13) |
C7A—N1A—C9A—C10A | −169.6 (10) | C7C—N1C—C9C—C10C | 177.5 (11) |
C8A—N1A—C9A—C11A | −174.5 (11) | C8C—N1C—C9C—C11C | 174.8 (10) |
C7A—N1A—C9A—C11A | 14.2 (18) | C7C—N1C—C9C—C11C | −5.5 (18) |
C10A—C9A—C11A—C16A | 90.0 (17) | C10C—C9C—C11C—C16C | −120.3 (15) |
N1A—C9A—C11A—C16A | −94.8 (15) | N1C—C9C—C11C—C16C | 63.6 (17) |
C10A—C9A—C11A—C12A | −89.4 (16) | C10C—C9C—C11C—C12C | 59.2 (18) |
N1A—C9A—C11A—C12A | 85.9 (15) | N1C—C9C—C11C—C12C | −116.9 (13) |
C16A—C11A—C12A—C13A | −2.1 (19) | C16C—C11C—C12C—C13C | −0.5 (19) |
C9A—C11A—C12A—C13A | 177.2 (12) | C9C—C11C—C12C—C13C | −180.0 (12) |
C11A—C12A—C13A—C14A | 1 (2) | C11C—C12C—C13C—C14C | 0 (2) |
C12A—C13A—C14A—C15A | 0 (2) | C12C—C13C—C14C—C15C | 1 (2) |
C13A—C14A—C15A—C16A | −0.1 (19) | C13C—C14C—C15C—C16C | −1 (2) |
C12A—C11A—C16A—C15A | 1.9 (18) | C12C—C11C—C16C—C15C | 0 (2) |
C9A—C11A—C16A—C15A | −177.4 (11) | C9C—C11C—C16C—C15C | 179.8 (12) |
C14A—C15A—C16A—C11A | −0.8 (19) | C14C—C15C—C16C—C11C | 0 (2) |
N1A—C9A—C10A—N2A | −2.2 (13) | N1C—C9C—C10C—N2C | 0.6 (13) |
C11A—C9A—C10A—N2A | 173.7 (12) | C11C—C9C—C10C—N2C | −176.0 (12) |
N1A—C9A—C10A—C17A | 174.8 (12) | N1C—C9C—C10C—C17C | −173.3 (12) |
C11A—C9A—C10A—C17A | −9 (2) | C11C—C9C—C10C—C17C | 10 (2) |
C9A—C10A—C17A—C22A | −68.6 (19) | C9C—C10C—C17C—C22C | 65.5 (17) |
N2A—C10A—C17A—C22A | 107.8 (15) | N2C—C10C—C17C—C22C | −107.5 (14) |
C9A—C10A—C17A—C18A | 110.8 (16) | C9C—C10C—C17C—C18C | −113.8 (15) |
N2A—C10A—C17A—C18A | −72.8 (17) | N2C—C10C—C17C—C18C | 73.2 (16) |
C22A—C17A—C18A—C19A | 2 (2) | C22C—C17C—C18C—C19C | −0.1 (17) |
C10A—C17A—C18A—C19A | −177.9 (13) | C10C—C17C—C18C—C19C | 179.2 (11) |
C17A—C18A—C19A—C20A | 0 (2) | C17C—C18C—C19C—C20C | 0.4 (18) |
C18A—C19A—C20A—C21A | −1 (3) | C18C—C19C—C20C—C21C | −0.9 (19) |
C19A—C20A—C21A—C22A | 0 (3) | C19C—C20C—C21C—C22C | 0.9 (19) |
C18A—C17A—C22A—C21A | −3 (2) | C18C—C17C—C22C—C21C | 0.2 (18) |
C10A—C17A—C22A—C21A | 176.9 (14) | C10C—C17C—C22C—C21C | −179.1 (11) |
C20A—C21A—C22A—C17A | 2 (3) | C20C—C21C—C22C—C17C | −0.6 (19) |
N1A—C8A—N2A—C10A | −1.0 (12) | N1C—C8C—N2C—C10C | −2.4 (12) |
Au1A—C8A—N2A—C10A | −179.5 (8) | Au1C—C8C—N2C—C10C | −179.6 (7) |
N1A—C8A—N2A—C23A | 175.2 (10) | N1C—C8C—N2C—C23C | −176.7 (9) |
Au1A—C8A—N2A—C23A | −3.3 (16) | Au1C—C8C—N2C—C23C | 6.1 (14) |
C9A—C10A—N2A—C8A | 2.0 (13) | C9C—C10C—N2C—C8C | 1.1 (13) |
C17A—C10A—N2A—C8A | −175.0 (12) | C17C—C10C—N2C—C8C | 175.4 (11) |
C9A—C10A—N2A—C23A | −174.1 (11) | C9C—C10C—N2C—C23C | 175.4 (10) |
C17A—C10A—N2A—C23A | 8.8 (19) | C17C—C10C—N2C—C23C | −10.3 (18) |
C8A—N2A—C23A—C24A | 112.6 (12) | C8C—N2C—C23C—C24C | −88.0 (13) |
C10A—N2A—C23A—C24A | −71.8 (14) | C10C—N2C—C23C—C24C | 98.5 (13) |
N2A—C23A—C24A—C29A | 128.5 (12) | N2C—C23C—C24C—C29C | 160.6 (10) |
N2A—C23A—C24A—C25A | −55.1 (15) | N2C—C23C—C24C—C25C | −21.8 (15) |
C29A—C24A—C25A—C26A | 0.0 (19) | C29C—C24C—C25C—C26C | 0.5 (17) |
C23A—C24A—C25A—C26A | −176.5 (12) | C23C—C24C—C25C—C26C | −177.2 (11) |
C24A—C25A—C26A—C27A | 0 (2) | C24C—C25C—C26C—C27C | −0.6 (18) |
C25A—C26A—C27A—C28A | −1 (2) | C25C—C26C—C27C—C28C | 0 (2) |
C26A—C27A—C28A—C29A | 1 (2) | C26C—C27C—C28C—C29C | 0 (2) |
C25A—C24A—C29A—C28A | 0.1 (19) | C25C—C24C—C29C—C28C | −0.3 (18) |
C23A—C24A—C29A—C28A | 176.6 (11) | C23C—C24C—C29C—C28C | 177.4 (11) |
C27A—C28A—C29A—C24A | −1 (2) | C27C—C28C—C29C—C24C | 0 (2) |
C6B—C1B—C2B—C3B | −0.5 (18) | C6D—C1D—C2D—C3D | −2 (2) |
C1B—C2B—C3B—C4B | 0 (2) | C1D—C2D—C3D—C4D | 1 (2) |
C2B—C3B—C4B—C5B | 0 (2) | C2D—C3D—C4D—C5D | −1 (2) |
C3B—C4B—C5B—C6B | 0 (2) | C3D—C4D—C5D—C6D | 1 (2) |
C4B—C5B—C6B—C1B | −0.6 (18) | C4D—C5D—C6D—C1D | −1.1 (19) |
C4B—C5B—C6B—C7B | −179.5 (11) | C4D—C5D—C6D—C7D | −177.2 (11) |
C2B—C1B—C6B—C5B | 0.8 (17) | C2D—C1D—C6D—C5D | 2 (2) |
C2B—C1B—C6B—C7B | 179.7 (10) | C2D—C1D—C6D—C7D | 177.8 (13) |
C5B—C6B—C7B—N1B | 113.2 (12) | C5D—C6D—C7D—N1D | −21.5 (16) |
C1B—C6B—C7B—N1B | −65.7 (13) | C1D—C6D—C7D—N1D | 162.4 (11) |
C6B—C7B—N1B—C8B | 106.3 (13) | C6D—C7D—N1D—C8D | −85.1 (13) |
C6B—C7B—N1B—C9B | −74.1 (15) | C6D—C7D—N1D—C9D | 97.6 (13) |
C9B—N1B—C8B—N2B | −0.2 (14) | C9D—N1D—C8D—N2D | 1.3 (12) |
C7B—N1B—C8B—N2B | 179.4 (11) | C7D—N1D—C8D—N2D | −176.3 (10) |
C9B—N1B—C8B—Au1B | −177.5 (9) | C9D—N1D—C8D—Au1D | 176.4 (8) |
C7B—N1B—C8B—Au1B | 2.1 (19) | C7D—N1D—C8D—Au1D | −1.2 (15) |
C8B—N1B—C9B—C10B | 0.5 (14) | C8D—N1D—C9D—C10D | −1.4 (13) |
C7B—N1B—C9B—C10B | −179.2 (11) | C7D—N1D—C9D—C10D | 176.1 (11) |
C8B—N1B—C9B—C11B | −175.6 (12) | C8D—N1D—C9D—C11D | 177.7 (11) |
C7B—N1B—C9B—C11B | 5 (2) | C7D—N1D—C9D—C11D | −4.8 (18) |
C10B—C9B—C11B—C12B | 113.5 (16) | C10D—C9D—C11D—C16D | −100.2 (16) |
N1B—C9B—C11B—C12B | −71.4 (17) | N1D—C9D—C11D—C16D | 81.0 (15) |
C10B—C9B—C11B—C16B | −66.3 (19) | C10D—C9D—C11D—C12D | 79.7 (17) |
N1B—C9B—C11B—C16B | 108.8 (14) | N1D—C9D—C11D—C12D | −99.1 (14) |
C16B—C11B—C12B—C13B | 0.7 (18) | C16D—C11D—C12D—C13D | −0.7 (18) |
C9B—C11B—C12B—C13B | −179.1 (11) | C9D—C11D—C12D—C13D | 179.4 (11) |
C11B—C12B—C13B—C14B | 0 (2) | C11D—C12D—C13D—C14D | 0.9 (19) |
C12B—C13B—C14B—C15B | 0 (2) | C12D—C13D—C14D—C15D | −1.0 (19) |
C13B—C14B—C15B—C16B | 1 (2) | C13D—C14D—C15D—C16D | 1 (2) |
C14B—C15B—C16B—C11B | −1 (2) | C12D—C11D—C16D—C15D | 0.5 (18) |
C12B—C11B—C16B—C15B | 0 (2) | C9D—C11D—C16D—C15D | −179.6 (11) |
C9B—C11B—C16B—C15B | 179.5 (13) | C14D—C15D—C16D—C11D | −1 (2) |
N1B—C9B—C10B—N2B | −0.5 (14) | N1D—C9D—C10D—N2D | 1.0 (13) |
C11B—C9B—C10B—N2B | 175.2 (13) | C11D—C9D—C10D—N2D | −178.0 (12) |
N1B—C9B—C10B—C17B | 176.5 (12) | N1D—C9D—C10D—C17D | −175.5 (13) |
C11B—C9B—C10B—C17B | −8 (2) | C11D—C9D—C10D—C17D | 6 (2) |
C9B—C10B—C17B—C18B | 119.2 (15) | C9D—C10D—C17D—C18D | −113.5 (16) |
N2B—C10B—C17B—C18B | −64.3 (16) | N2D—C10D—C17D—C18D | 70.5 (17) |
C9B—C10B—C17B—C22B | −59.8 (18) | C9D—C10D—C17D—C22D | 66.5 (18) |
N2B—C10B—C17B—C22B | 116.7 (13) | N2D—C10D—C17D—C22D | −109.5 (13) |
C22B—C17B—C18B—C19B | −1.1 (18) | C22D—C17D—C18D—C19D | 1 (2) |
C10B—C17B—C18B—C19B | −180.0 (11) | C10D—C17D—C18D—C19D | −179.2 (13) |
C17B—C18B—C19B—C20B | 1 (2) | C17D—C18D—C19D—C20D | 0 (2) |
C18B—C19B—C20B—C21B | 0 (2) | C18D—C19D—C20D—C21D | 0 (3) |
C19B—C20B—C21B—C22B | −1.4 (19) | C19D—C20D—C21D—C22D | 1 (2) |
C18B—C17B—C22B—C21B | −0.3 (18) | C18D—C17D—C22D—C21D | −0.2 (19) |
C10B—C17B—C22B—C21B | 178.7 (11) | C10D—C17D—C22D—C21D | 179.8 (11) |
C20B—C21B—C22B—C17B | 1.5 (19) | C20D—C21D—C22D—C17D | −1 (2) |
N1B—C8B—N2B—C10B | −0.2 (14) | N1D—C8D—N2D—C10D | −0.6 (12) |
Au1B—C8B—N2B—C10B | 177.3 (8) | Au1D—C8D—N2D—C10D | −175.7 (8) |
N1B—C8B—N2B—C23B | 174.7 (11) | N1D—C8D—N2D—C23D | −179.1 (11) |
Au1B—C8B—N2B—C23B | −7.9 (17) | Au1D—C8D—N2D—C23D | 5.9 (17) |
C9B—C10B—N2B—C8B | 0.4 (14) | C9D—C10D—N2D—C8D | −0.2 (14) |
C17B—C10B—N2B—C8B | −176.7 (11) | C17D—C10D—N2D—C8D | 176.6 (11) |
C9B—C10B—N2B—C23B | −174.3 (12) | C9D—C10D—N2D—C23D | 178.2 (11) |
C17B—C10B—N2B—C23B | 8.5 (19) | C17D—C10D—N2D—C23D | −5.0 (19) |
C8B—N2B—C23B—C24B | 94.0 (14) | C8D—N2D—C23D—C24D | −116.9 (12) |
C10B—N2B—C23B—C24B | −92.0 (14) | C10D—N2D—C23D—C24D | 64.9 (16) |
N2B—C23B—C24B—C29B | −10.3 (17) | N2D—C23D—C24D—C29D | 51.5 (16) |
N2B—C23B—C24B—C25B | 171.9 (11) | N2D—C23D—C24D—C25D | −126.5 (13) |
C29B—C24B—C25B—C26B | −1 (2) | C29D—C24D—C25D—C26D | 0 (2) |
C23B—C24B—C25B—C26B | 176.8 (13) | C23D—C24D—C25D—C26D | 178.0 (14) |
C24B—C25B—C26B—C27B | 0 (2) | C24D—C25D—C26D—C27D | 0 (3) |
C25B—C26B—C27B—C28B | 2 (3) | C25D—C26D—C27D—C28D | 0 (3) |
C26B—C27B—C28B—C29B | −2 (2) | C26D—C27D—C28D—C29D | 1 (3) |
C25B—C24B—C29B—C28B | 1 (2) | C25D—C24D—C29D—C28D | 1 (2) |
C23B—C24B—C29B—C28B | −176.9 (12) | C23D—C24D—C29D—C28D | −177.5 (13) |
C27B—C28B—C29B—C24B | 1 (2) | C27D—C28D—C29D—C24D | −1 (2) |
Selected bond lengths and angles (Å, °) for (1) and (2) topX = Cl for (1) and Br for (2). |
| 1 | (2), molecule A | (2), molecule B | (2), molecule C | (2), molecule D | Variation within (2) (largest individual s.u.) |
Au—X | 2.3013 (6) | 2.4796 (12) | 2.4789 (11) | 2.4354 (13) | 2.4279 (14) | 0.0517 (14) |
Au—C8 | 1.976 (3) | 1.997 (10) | 2.013 (11) | 2.016 (10) | 1.969 (12) | 0.047 (12) |
C8—N1 | 1.367 (3) | 1.354 (14) | 1.328 (14) | 1.328 (13) | 1.359 (14) | 0.031 (14) |
C8—N2 | 1.346 (4) | 1.356 (13) | 1.345 (14) | 1.339 (13) | 1.361 (15) | 0.023 (15) |
N1—C9 | 1.381 (4) | 1.404 (13) | 1.386 (14) | 1.385 (14) | 1.386 (14) | 0.019 (15) |
C9—C10 | 1.350 (4) | 1.349 (16) | 1.343 (16) | 1.341 (15) | 1.350 (16) | 0.009 (16) |
C10—N2 | 1.385 (3) | 1.377 (13) | 1.391 (14) | 1.379 (14) | 1.382 (15) | 0.014 (15) |
| | | | | | |
N1—C8—N2 | 104.7 (2) | 105.5 (8) | 106.9 (9) | 106.6 (9) | 103.9 (10) | |
C9—N1—C8 | 111.1 (2) | 109.9 (9) | 109.7 (9) | 109.8 (9) | 112.0 (9) | |
C10—C9—N1 | 106.0 (2) | 106.6 (9) | 107.4 (9) | 106.9 (9) | 105.5 (10) | |
N2—C10—C9 | 107.6 (3) | 107.1 (9) | 106.3 (10) | 106.6 (10) | 107.7 (11) | |
C8—N2—C10 | 110.6 (2) | 110.9 (9) | 109.6 (9) | 110.0 (9) | 110.8 (10) | |
Centroid positions of the four independent molecules in (2) top | Centroid x | Centroid y | Centroid z |
Molecule A | 0.324 | 0.770 | 0.735 |
Molecule B | 0.180 | 0.783 | 0.233 |
Molecule C | 0.782 | 0.650 | 0.943 |
Molecule D | 0.798 | 0.655 | 0.443 |