The title complex was synthesized by ligand metathesis from [1,3-bis(2,6-diisopropylphenyl)imidazol-2-ylidene]gold(I) chloride and sodium cyanate in anhydrous tetrahydrofuran and crystallized from toluene at 233 K as a neutral complex with the central Au atom di-coordinated by an N-heterocyclic carbene and an isocyanate, with a linear CAuNCO moiety.
Supporting information
CCDC reference: 2306677
[1,3-Bis(2,6-diisopropylphenyl)imidazol-2-ylidene](isocyanato-
κN)gold(I)
top
Crystal data top
[Au(NCO)(C27H36N2)] | Dx = 1.540 Mg m−3 |
Mr = 627.56 | Mo Kα radiation, λ = 0.71073 Å |
Orthorhombic, P212121 | Cell parameters from 9267 reflections |
a = 10.3941 (7) Å | θ = 2.6–28.3° |
b = 11.1540 (7) Å | µ = 5.46 mm−1 |
c = 23.3489 (15) Å | T = 100 K |
V = 2707.0 (3) Å3 | Prism, colourless |
Z = 4 | 0.18 × 0.17 × 0.12 mm |
F(000) = 1248 | |
Data collection top
Bruker D8 Quest/Photon 100 diffractometer | 6680 independent reflections |
Radiation source: microfocus sealed tube | 6610 reflections with I > 2σ(I) |
Multilayer mirrors monochromator | Rint = 0.029 |
profile data from φ and ω scans | θmax = 28.4°, θmin = 2.5° |
Absorption correction: multi-scan (SADABS; Krause et al., 2015) | h = −13→13 |
Tmin = 0.512, Tmax = 0.710 | k = −14→14 |
76237 measured reflections | l = −31→31 |
Refinement top
Refinement on F2 | Hydrogen site location: inferred from neighbouring sites |
Least-squares matrix: full | H atoms treated by a mixture of independent and constrained refinement |
R[F2 > 2σ(F2)] = 0.013 | w = 1/[σ2(Fo2) + (0.0022P)2 + 0.5084P] where P = (Fo2 + 2Fc2)/3 |
wR(F2) = 0.025 | (Δ/σ)max = 0.003 |
S = 1.11 | Δρmax = 0.61 e Å−3 |
6680 reflections | Δρmin = −0.31 e Å−3 |
315 parameters | Extinction correction: SHELXL2019/1 (Sheldrick, 2015b), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4 |
0 restraints | Extinction coefficient: 0.00303 (9) |
Primary atom site location: dual | Absolute structure: Flack x determined using 2845 quotients
[(I+)-(I-)]/[(I+)+(I-)]
(Parsons et al., 2013) |
Secondary atom site location: difference Fourier map | Absolute structure parameter: 0.007 (2) |
Special details top
Experimental. One distinct cell was identified using APEX3 (Bruker, 2016). Six
frame series were integrated and filtered for statistical outliers
using SAINT (Bruker, 2016) then corrected for absorption by integration
using SAINT/SADABS v2014/2 (Bruker, 2016) to sort, merge, and scale
the combined data. No decay correction was applied. |
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. Structure was phased by intrinsic methods (Sheldrick, 2015a). Systematic
conditions suggested the ambiguous space group. The space group choice was
confirmed by successful convergence of the full-matrix least-squares
refinement on F2. The final map had no significant features. A final
analysis of variance between observed and calculated structure factors
showed little dependence on amplitude and resolution. |
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top | x | y | z | Uiso*/Ueq | |
Au1 | 0.26753 (2) | 0.23607 (2) | 0.37741 (2) | 0.01629 (3) | |
O1 | 0.2821 (2) | −0.14249 (15) | 0.41879 (9) | 0.0378 (5) | |
N1 | 0.2343 (2) | 0.49912 (15) | 0.39199 (7) | 0.0157 (4) | |
N2 | 0.2784 (2) | 0.45853 (16) | 0.30454 (7) | 0.0151 (4) | |
N3 | 0.2667 (3) | 0.06303 (19) | 0.39972 (9) | 0.0283 (5) | |
C1 | 0.2625 (2) | 0.40636 (18) | 0.35634 (9) | 0.0148 (4) | |
C2 | 0.2332 (2) | 0.6070 (2) | 0.36284 (10) | 0.0197 (5) | |
H2 | 0.221 (2) | 0.680 (2) | 0.3819 (10) | 0.023 (7)* | |
C3 | 0.2606 (3) | 0.58160 (19) | 0.30804 (10) | 0.0190 (5) | |
H3 | 0.270 (3) | 0.629 (2) | 0.2773 (10) | 0.017 (6)* | |
C4 | 0.2132 (2) | 0.4847 (2) | 0.45287 (9) | 0.0168 (5) | |
C5 | 0.0907 (2) | 0.4478 (2) | 0.47107 (11) | 0.0193 (5) | |
C6 | 0.0742 (3) | 0.4320 (2) | 0.52988 (12) | 0.0246 (6) | |
H6 | −0.006924 | 0.406579 | 0.544201 | 0.029* | |
C7 | 0.1742 (3) | 0.4528 (2) | 0.56757 (11) | 0.0267 (6) | |
H7 | 0.161106 | 0.441254 | 0.607458 | 0.032* | |
C8 | 0.2930 (3) | 0.4900 (2) | 0.54798 (10) | 0.0259 (6) | |
H8 | 0.360466 | 0.503938 | 0.574613 | 0.031* | |
C9 | 0.3155 (2) | 0.5077 (2) | 0.48950 (10) | 0.0208 (5) | |
C10 | −0.0199 (2) | 0.4307 (2) | 0.42925 (12) | 0.0229 (6) | |
H10 | 0.017665 | 0.416710 | 0.390388 | 0.027* | |
C11 | −0.1042 (3) | 0.3230 (3) | 0.44407 (15) | 0.0394 (8) | |
H11A | −0.171818 | 0.314256 | 0.415116 | 0.059* | |
H11B | −0.143619 | 0.335255 | 0.481746 | 0.059* | |
H11C | −0.051310 | 0.250252 | 0.444865 | 0.059* | |
C12 | −0.1010 (3) | 0.5452 (3) | 0.42656 (13) | 0.0329 (7) | |
H12A | −0.046152 | 0.612932 | 0.415753 | 0.049* | |
H12B | −0.139480 | 0.560496 | 0.464170 | 0.049* | |
H12C | −0.169343 | 0.535288 | 0.398019 | 0.049* | |
C13 | 0.4476 (3) | 0.5458 (3) | 0.46822 (11) | 0.0264 (6) | |
H13 | 0.438282 | 0.567922 | 0.426931 | 0.032* | |
C14 | 0.4986 (3) | 0.6556 (3) | 0.49942 (12) | 0.0413 (8) | |
H14A | 0.581927 | 0.678645 | 0.483126 | 0.062* | |
H14B | 0.509191 | 0.637001 | 0.540165 | 0.062* | |
H14C | 0.437623 | 0.721984 | 0.495059 | 0.062* | |
C15 | 0.5423 (3) | 0.4419 (3) | 0.47129 (18) | 0.0453 (9) | |
H15A | 0.504052 | 0.370822 | 0.453394 | 0.068* | |
H15B | 0.562278 | 0.424411 | 0.511450 | 0.068* | |
H15C | 0.621502 | 0.463457 | 0.450996 | 0.068* | |
C16 | 0.3151 (2) | 0.3971 (2) | 0.25267 (10) | 0.0171 (5) | |
C17 | 0.4467 (3) | 0.3911 (2) | 0.23968 (11) | 0.0207 (6) | |
C18 | 0.4805 (3) | 0.3365 (2) | 0.18834 (11) | 0.0270 (6) | |
H18 | 0.568715 | 0.330687 | 0.177981 | 0.032* | |
C19 | 0.3877 (3) | 0.2906 (3) | 0.15223 (11) | 0.0293 (6) | |
H19 | 0.412772 | 0.254023 | 0.117211 | 0.035* | |
C20 | 0.2586 (3) | 0.2971 (2) | 0.16641 (10) | 0.0266 (5) | |
H20 | 0.196098 | 0.264555 | 0.141130 | 0.032* | |
C21 | 0.2193 (3) | 0.3511 (2) | 0.21743 (10) | 0.0205 (5) | |
C22 | 0.5492 (3) | 0.4415 (3) | 0.27965 (12) | 0.0259 (6) | |
H22 | 0.503778 | 0.484144 | 0.311436 | 0.031* | |
C23 | 0.6350 (4) | 0.5327 (4) | 0.24968 (15) | 0.0524 (10) | |
H23A | 0.681140 | 0.493551 | 0.218227 | 0.079* | |
H23B | 0.697090 | 0.565354 | 0.277140 | 0.079* | |
H23C | 0.581895 | 0.597885 | 0.234403 | 0.079* | |
C24 | 0.6274 (4) | 0.3407 (3) | 0.30637 (17) | 0.0595 (11) | |
H24A | 0.679597 | 0.301835 | 0.276762 | 0.089* | |
H24B | 0.569013 | 0.281642 | 0.323466 | 0.089* | |
H24C | 0.683788 | 0.373548 | 0.336097 | 0.089* | |
C25 | 0.0776 (3) | 0.3555 (3) | 0.23361 (12) | 0.0261 (6) | |
H25 | 0.068802 | 0.410186 | 0.267309 | 0.031* | |
C26 | 0.0316 (3) | 0.2308 (3) | 0.25208 (13) | 0.0390 (7) | |
H26A | 0.036322 | 0.175785 | 0.219407 | 0.059* | |
H26B | −0.057475 | 0.235788 | 0.265587 | 0.059* | |
H26C | 0.086646 | 0.200985 | 0.283054 | 0.059* | |
C27 | −0.0068 (3) | 0.4051 (3) | 0.18560 (13) | 0.0375 (8) | |
H27A | 0.025228 | 0.484162 | 0.174054 | 0.056* | |
H27B | −0.095587 | 0.412489 | 0.199211 | 0.056* | |
H27C | −0.004031 | 0.350569 | 0.152718 | 0.056* | |
C28 | 0.2743 (3) | −0.0363 (2) | 0.40865 (10) | 0.0218 (5) | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
Au1 | 0.01867 (5) | 0.01490 (5) | 0.01529 (4) | 0.00074 (3) | −0.00236 (3) | 0.00049 (3) |
O1 | 0.0479 (13) | 0.0154 (9) | 0.0502 (12) | −0.0026 (9) | 0.0055 (11) | 0.0016 (8) |
N1 | 0.0162 (10) | 0.0178 (10) | 0.0132 (9) | 0.0007 (8) | −0.0020 (8) | −0.0020 (6) |
N2 | 0.0162 (10) | 0.0153 (9) | 0.0137 (9) | 0.0017 (9) | −0.0004 (8) | −0.0009 (7) |
N3 | 0.0358 (14) | 0.0224 (11) | 0.0268 (11) | 0.0023 (12) | −0.0081 (11) | 0.0032 (8) |
C1 | 0.0122 (11) | 0.0174 (10) | 0.0148 (10) | −0.0004 (10) | −0.0013 (9) | 0.0008 (8) |
C2 | 0.0213 (12) | 0.0143 (10) | 0.0235 (12) | 0.0016 (10) | −0.0008 (11) | −0.0022 (9) |
C3 | 0.0213 (13) | 0.0164 (11) | 0.0192 (11) | 0.0002 (11) | −0.0006 (11) | 0.0034 (9) |
C4 | 0.0198 (12) | 0.0179 (11) | 0.0125 (10) | 0.0034 (10) | 0.0006 (9) | −0.0020 (8) |
C5 | 0.0163 (12) | 0.0209 (13) | 0.0208 (13) | 0.0043 (10) | 0.0011 (10) | −0.0030 (10) |
C6 | 0.0224 (15) | 0.0298 (15) | 0.0215 (14) | 0.0038 (11) | 0.0067 (11) | −0.0012 (11) |
C7 | 0.0326 (15) | 0.0326 (16) | 0.0149 (12) | 0.0032 (12) | 0.0035 (11) | −0.0016 (11) |
C8 | 0.0252 (14) | 0.0341 (15) | 0.0184 (12) | 0.0012 (11) | −0.0049 (10) | −0.0032 (10) |
C9 | 0.0204 (12) | 0.0225 (14) | 0.0194 (13) | −0.0002 (10) | −0.0014 (10) | −0.0016 (10) |
C10 | 0.0155 (12) | 0.0300 (15) | 0.0232 (14) | 0.0001 (11) | 0.0009 (10) | −0.0024 (11) |
C11 | 0.0345 (17) | 0.0296 (16) | 0.054 (2) | −0.0079 (13) | −0.0191 (15) | 0.0070 (14) |
C12 | 0.0256 (15) | 0.0304 (16) | 0.0425 (17) | 0.0015 (12) | −0.0100 (13) | 0.0063 (13) |
C13 | 0.0205 (13) | 0.0397 (17) | 0.0190 (13) | −0.0062 (12) | −0.0051 (11) | 0.0025 (12) |
C14 | 0.046 (2) | 0.0443 (19) | 0.0339 (19) | −0.0176 (16) | −0.0041 (15) | 0.0028 (14) |
C15 | 0.0194 (17) | 0.048 (2) | 0.068 (3) | −0.0007 (15) | 0.0118 (16) | 0.0029 (18) |
C16 | 0.0225 (12) | 0.0167 (11) | 0.0121 (11) | 0.0022 (10) | 0.0013 (9) | 0.0012 (9) |
C17 | 0.0229 (13) | 0.0197 (13) | 0.0194 (13) | 0.0014 (11) | 0.0024 (10) | 0.0015 (10) |
C18 | 0.0259 (15) | 0.0301 (15) | 0.0249 (14) | 0.0052 (12) | 0.0070 (11) | 0.0020 (12) |
C19 | 0.0391 (16) | 0.0325 (16) | 0.0163 (12) | 0.0090 (12) | 0.0028 (11) | −0.0049 (11) |
C20 | 0.0339 (15) | 0.0279 (12) | 0.0180 (11) | 0.0044 (12) | −0.0064 (11) | −0.0050 (9) |
C21 | 0.0233 (13) | 0.0205 (11) | 0.0176 (11) | 0.0015 (11) | −0.0019 (10) | 0.0014 (9) |
C22 | 0.0192 (14) | 0.0299 (16) | 0.0287 (15) | −0.0010 (12) | 0.0051 (11) | −0.0059 (12) |
C23 | 0.047 (2) | 0.059 (2) | 0.051 (2) | −0.027 (2) | 0.0122 (18) | −0.0087 (19) |
C24 | 0.060 (2) | 0.047 (2) | 0.071 (3) | 0.0126 (18) | −0.045 (2) | −0.0157 (19) |
C25 | 0.0215 (14) | 0.0371 (17) | 0.0198 (14) | 0.0017 (12) | −0.0026 (11) | −0.0029 (12) |
C26 | 0.0282 (14) | 0.0491 (19) | 0.0397 (16) | −0.0129 (15) | −0.0086 (12) | 0.0063 (16) |
C27 | 0.0280 (16) | 0.054 (2) | 0.0302 (17) | 0.0101 (15) | −0.0068 (13) | −0.0018 (15) |
C28 | 0.0220 (13) | 0.0270 (14) | 0.0163 (12) | −0.0029 (12) | 0.0008 (11) | −0.0052 (9) |
Geometric parameters (Å, º) top
Au1—N3 | 1.999 (2) | C14—H14A | 0.9800 |
Au1—C1 | 1.963 (2) | C14—H14B | 0.9800 |
O1—C28 | 1.210 (3) | C14—H14C | 0.9800 |
N1—C1 | 1.360 (3) | C15—H15A | 0.9800 |
N1—C2 | 1.382 (3) | C15—H15B | 0.9800 |
N1—C4 | 1.447 (3) | C15—H15C | 0.9800 |
N2—C1 | 1.352 (3) | C16—C17 | 1.402 (4) |
N2—C3 | 1.387 (3) | C16—C21 | 1.390 (3) |
N2—C16 | 1.443 (3) | C17—C18 | 1.390 (4) |
N3—C28 | 1.130 (3) | C17—C22 | 1.524 (4) |
C2—H2 | 0.94 (3) | C18—H18 | 0.9500 |
C2—C3 | 1.341 (3) | C18—C19 | 1.380 (4) |
C3—H3 | 0.89 (2) | C19—H19 | 0.9500 |
C4—C5 | 1.404 (3) | C19—C20 | 1.384 (4) |
C4—C9 | 1.388 (3) | C20—H20 | 0.9500 |
C5—C6 | 1.395 (4) | C20—C21 | 1.396 (3) |
C5—C10 | 1.520 (3) | C21—C25 | 1.521 (4) |
C6—H6 | 0.9500 | C22—H22 | 1.0000 |
C6—C7 | 1.382 (4) | C22—C23 | 1.523 (4) |
C7—H7 | 0.9500 | C22—C24 | 1.521 (4) |
C7—C8 | 1.381 (4) | C23—H23A | 0.9800 |
C8—H8 | 0.9500 | C23—H23B | 0.9800 |
C8—C9 | 1.399 (3) | C23—H23C | 0.9800 |
C9—C13 | 1.521 (4) | C24—H24A | 0.9800 |
C10—H10 | 1.0000 | C24—H24B | 0.9800 |
C10—C11 | 1.527 (4) | C24—H24C | 0.9800 |
C10—C12 | 1.532 (4) | C25—H25 | 1.0000 |
C11—H11A | 0.9800 | C25—C26 | 1.533 (4) |
C11—H11B | 0.9800 | C25—C27 | 1.527 (4) |
C11—H11C | 0.9800 | C26—H26A | 0.9800 |
C12—H12A | 0.9800 | C26—H26B | 0.9800 |
C12—H12B | 0.9800 | C26—H26C | 0.9800 |
C12—H12C | 0.9800 | C27—H27A | 0.9800 |
C13—H13 | 1.0000 | C27—H27B | 0.9800 |
C13—C14 | 1.521 (4) | C27—H27C | 0.9800 |
C13—C15 | 1.522 (4) | | |
| | | |
C1—Au1—N3 | 178.14 (11) | H14A—C14—H14C | 109.5 |
C1—N1—C2 | 111.26 (18) | H14B—C14—H14C | 109.5 |
C1—N1—C4 | 123.35 (18) | C13—C15—H15A | 109.5 |
C2—N1—C4 | 125.36 (18) | C13—C15—H15B | 109.5 |
C1—N2—C3 | 110.91 (18) | C13—C15—H15C | 109.5 |
C1—N2—C16 | 125.33 (18) | H15A—C15—H15B | 109.5 |
C3—N2—C16 | 123.69 (18) | H15A—C15—H15C | 109.5 |
C28—N3—Au1 | 173.8 (2) | H15B—C15—H15C | 109.5 |
N1—C1—Au1 | 126.05 (16) | C17—C16—N2 | 117.5 (2) |
N2—C1—Au1 | 129.61 (16) | C21—C16—N2 | 118.8 (2) |
N2—C1—N1 | 104.26 (17) | C21—C16—C17 | 123.6 (2) |
N1—C2—H2 | 121.6 (15) | C16—C17—C22 | 122.1 (2) |
C3—C2—N1 | 106.53 (19) | C18—C17—C16 | 117.0 (2) |
C3—C2—H2 | 131.7 (15) | C18—C17—C22 | 120.8 (2) |
N2—C3—H3 | 121.3 (15) | C17—C18—H18 | 119.6 |
C2—C3—N2 | 107.05 (19) | C19—C18—C17 | 120.8 (3) |
C2—C3—H3 | 131.7 (15) | C19—C18—H18 | 119.6 |
C5—C4—N1 | 117.9 (2) | C18—C19—H19 | 119.6 |
C9—C4—N1 | 117.9 (2) | C18—C19—C20 | 120.8 (2) |
C9—C4—C5 | 124.2 (2) | C20—C19—H19 | 119.6 |
C4—C5—C10 | 121.9 (2) | C19—C20—H20 | 119.6 |
C6—C5—C4 | 116.5 (2) | C19—C20—C21 | 120.7 (2) |
C6—C5—C10 | 121.5 (2) | C21—C20—H20 | 119.6 |
C5—C6—H6 | 119.6 | C16—C21—C20 | 117.0 (2) |
C7—C6—C5 | 120.9 (3) | C16—C21—C25 | 122.3 (2) |
C7—C6—H6 | 119.6 | C20—C21—C25 | 120.6 (2) |
C6—C7—H7 | 119.6 | C17—C22—H22 | 107.4 |
C8—C7—C6 | 120.8 (2) | C23—C22—C17 | 112.0 (2) |
C8—C7—H7 | 119.6 | C23—C22—H22 | 107.4 |
C7—C8—H8 | 119.5 | C24—C22—C17 | 110.6 (2) |
C7—C8—C9 | 121.0 (2) | C24—C22—H22 | 107.4 |
C9—C8—H8 | 119.5 | C24—C22—C23 | 111.7 (3) |
C4—C9—C8 | 116.6 (2) | C22—C23—H23A | 109.5 |
C4—C9—C13 | 122.8 (2) | C22—C23—H23B | 109.5 |
C8—C9—C13 | 120.6 (2) | C22—C23—H23C | 109.5 |
C5—C10—H10 | 107.9 | H23A—C23—H23B | 109.5 |
C5—C10—C11 | 112.8 (2) | H23A—C23—H23C | 109.5 |
C5—C10—C12 | 109.8 (2) | H23B—C23—H23C | 109.5 |
C11—C10—H10 | 107.9 | C22—C24—H24A | 109.5 |
C11—C10—C12 | 110.4 (2) | C22—C24—H24B | 109.5 |
C12—C10—H10 | 107.9 | C22—C24—H24C | 109.5 |
C10—C11—H11A | 109.5 | H24A—C24—H24B | 109.5 |
C10—C11—H11B | 109.5 | H24A—C24—H24C | 109.5 |
C10—C11—H11C | 109.5 | H24B—C24—H24C | 109.5 |
H11A—C11—H11B | 109.5 | C21—C25—H25 | 107.7 |
H11A—C11—H11C | 109.5 | C21—C25—C26 | 110.0 (2) |
H11B—C11—H11C | 109.5 | C21—C25—C27 | 112.7 (2) |
C10—C12—H12A | 109.5 | C26—C25—H25 | 107.7 |
C10—C12—H12B | 109.5 | C27—C25—H25 | 107.7 |
C10—C12—H12C | 109.5 | C27—C25—C26 | 110.9 (2) |
H12A—C12—H12B | 109.5 | C25—C26—H26A | 109.5 |
H12A—C12—H12C | 109.5 | C25—C26—H26B | 109.5 |
H12B—C12—H12C | 109.5 | C25—C26—H26C | 109.5 |
C9—C13—H13 | 107.2 | H26A—C26—H26B | 109.5 |
C9—C13—C15 | 110.8 (2) | H26A—C26—H26C | 109.5 |
C14—C13—C9 | 112.6 (2) | H26B—C26—H26C | 109.5 |
C14—C13—H13 | 107.2 | C25—C27—H27A | 109.5 |
C14—C13—C15 | 111.4 (3) | C25—C27—H27B | 109.5 |
C15—C13—H13 | 107.2 | C25—C27—H27C | 109.5 |
C13—C14—H14A | 109.5 | H27A—C27—H27B | 109.5 |
C13—C14—H14B | 109.5 | H27A—C27—H27C | 109.5 |
C13—C14—H14C | 109.5 | H27B—C27—H27C | 109.5 |
H14A—C14—H14B | 109.5 | N3—C28—O1 | 179.3 (3) |
| | | |
N1—C2—C3—N2 | −0.1 (3) | C5—C6—C7—C8 | 0.2 (4) |
N1—C4—C5—C6 | 178.5 (2) | C6—C5—C10—C11 | −40.7 (4) |
N1—C4—C5—C10 | −3.9 (3) | C6—C5—C10—C12 | 82.9 (3) |
N1—C4—C9—C8 | −178.4 (2) | C6—C7—C8—C9 | −0.1 (4) |
N1—C4—C9—C13 | −0.5 (4) | C7—C8—C9—C4 | −0.5 (4) |
N2—C16—C17—C18 | −177.2 (2) | C7—C8—C9—C13 | −178.5 (3) |
N2—C16—C17—C22 | 3.0 (4) | C8—C9—C13—C14 | −51.9 (3) |
N2—C16—C21—C20 | 177.1 (2) | C8—C9—C13—C15 | 73.7 (3) |
N2—C16—C21—C25 | −4.4 (3) | C9—C4—C5—C6 | −1.0 (4) |
C1—N1—C2—C3 | 0.2 (3) | C9—C4—C5—C10 | 176.5 (2) |
C1—N1—C4—C5 | −82.3 (3) | C10—C5—C6—C7 | −177.2 (2) |
C1—N1—C4—C9 | 97.3 (3) | C16—N2—C1—Au1 | −6.1 (4) |
C1—N2—C3—C2 | 0.0 (3) | C16—N2—C1—N1 | 177.3 (2) |
C1—N2—C16—C17 | −91.9 (3) | C16—N2—C3—C2 | −177.2 (2) |
C1—N2—C16—C21 | 90.3 (3) | C16—C17—C18—C19 | 0.0 (4) |
C2—N1—C1—Au1 | −177.09 (17) | C16—C17—C22—C23 | −124.0 (3) |
C2—N1—C1—N2 | −0.3 (3) | C16—C17—C22—C24 | 110.7 (3) |
C2—N1—C4—C5 | 100.1 (3) | C16—C21—C25—C26 | −105.2 (3) |
C2—N1—C4—C9 | −80.3 (3) | C16—C21—C25—C27 | 130.5 (3) |
C3—N2—C1—Au1 | 176.85 (18) | C17—C16—C21—C20 | −0.4 (4) |
C3—N2—C1—N1 | 0.2 (3) | C17—C16—C21—C25 | 178.1 (2) |
C3—N2—C16—C17 | 84.8 (3) | C17—C18—C19—C20 | −0.4 (4) |
C3—N2—C16—C21 | −92.9 (3) | C18—C17—C22—C23 | 56.1 (4) |
C4—N1—C1—Au1 | 5.0 (4) | C18—C17—C22—C24 | −69.2 (4) |
C4—N1—C1—N2 | −178.2 (2) | C18—C19—C20—C21 | 0.4 (4) |
C4—N1—C2—C3 | 178.1 (2) | C19—C20—C21—C16 | 0.0 (4) |
C4—C5—C6—C7 | 0.3 (4) | C19—C20—C21—C25 | −178.5 (2) |
C4—C5—C10—C11 | 141.9 (3) | C20—C21—C25—C26 | 73.2 (3) |
C4—C5—C10—C12 | −94.5 (3) | C20—C21—C25—C27 | −51.1 (3) |
C4—C9—C13—C14 | 130.3 (3) | C21—C16—C17—C18 | 0.4 (4) |
C4—C9—C13—C15 | −104.1 (3) | C21—C16—C17—C22 | −179.4 (2) |
C5—C4—C9—C8 | 1.1 (4) | C22—C17—C18—C19 | 179.8 (3) |
C5—C4—C9—C13 | 179.0 (2) | | |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
C2—H2···O1i | 0.94 (3) | 2.25 (3) | 3.127 (3) | 155 (2) |
Symmetry code: (i) x, y+1, z. |