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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

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S205698902400046X/zv2031sup1.cif
Contains datablock I

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S205698902400046X/zv2031Isup5.hkl
Contains datablock I

CCDC reference: 2306677

Computing details top

[1,3-Bis(2,6-diisopropylphenyl)imidazol-2-ylidene](isocyanato-κN)gold(I) top
Crystal data top
[Au(NCO)(C27H36N2)]Dx = 1.540 Mg m3
Mr = 627.56Mo Kα radiation, λ = 0.71073 Å
Orthorhombic, P212121Cell parameters from 9267 reflections
a = 10.3941 (7) Åθ = 2.6–28.3°
b = 11.1540 (7) ŵ = 5.46 mm1
c = 23.3489 (15) ÅT = 100 K
V = 2707.0 (3) Å3Prism, colourless
Z = 40.18 × 0.17 × 0.12 mm
F(000) = 1248
Data collection top
Bruker D8 Quest/Photon 100
diffractometer
6680 independent reflections
Radiation source: microfocus sealed tube6610 reflections with I > 2σ(I)
Multilayer mirrors monochromatorRint = 0.029
profile data from φ and ω scansθmax = 28.4°, θmin = 2.5°
Absorption correction: multi-scan
(SADABS; Krause et al., 2015)
h = 1313
Tmin = 0.512, Tmax = 0.710k = 1414
76237 measured reflectionsl = 3131
Refinement top
Refinement on F2Hydrogen site location: inferred from neighbouring sites
Least-squares matrix: fullH 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 = 1.11Δρmax = 0.61 e Å3
6680 reflectionsΔρmin = 0.31 e Å3
315 parametersExtinction correction: SHELXL2019/1 (Sheldrick, 2015b), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
0 restraintsExtinction coefficient: 0.00303 (9)
Primary atom site location: dualAbsolute structure: Flack x determined using 2845 quotients [(I+)-(I-)]/[(I+)+(I-)] (Parsons et al., 2013)
Secondary atom site location: difference Fourier mapAbsolute 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
xyzUiso*/Ueq
Au10.26753 (2)0.23607 (2)0.37741 (2)0.01629 (3)
O10.2821 (2)0.14249 (15)0.41879 (9)0.0378 (5)
N10.2343 (2)0.49912 (15)0.39199 (7)0.0157 (4)
N20.2784 (2)0.45853 (16)0.30454 (7)0.0151 (4)
N30.2667 (3)0.06303 (19)0.39972 (9)0.0283 (5)
C10.2625 (2)0.40636 (18)0.35634 (9)0.0148 (4)
C20.2332 (2)0.6070 (2)0.36284 (10)0.0197 (5)
H20.221 (2)0.680 (2)0.3819 (10)0.023 (7)*
C30.2606 (3)0.58160 (19)0.30804 (10)0.0190 (5)
H30.270 (3)0.629 (2)0.2773 (10)0.017 (6)*
C40.2132 (2)0.4847 (2)0.45287 (9)0.0168 (5)
C50.0907 (2)0.4478 (2)0.47107 (11)0.0193 (5)
C60.0742 (3)0.4320 (2)0.52988 (12)0.0246 (6)
H60.0069240.4065790.5442010.029*
C70.1742 (3)0.4528 (2)0.56757 (11)0.0267 (6)
H70.1611060.4412540.6074580.032*
C80.2930 (3)0.4900 (2)0.54798 (10)0.0259 (6)
H80.3604660.5039380.5746130.031*
C90.3155 (2)0.5077 (2)0.48950 (10)0.0208 (5)
C100.0199 (2)0.4307 (2)0.42925 (12)0.0229 (6)
H100.0176650.4167100.3903880.027*
C110.1042 (3)0.3230 (3)0.44407 (15)0.0394 (8)
H11A0.1718180.3142560.4151160.059*
H11B0.1436190.3352550.4817460.059*
H11C0.0513100.2502520.4448650.059*
C120.1010 (3)0.5452 (3)0.42656 (13)0.0329 (7)
H12A0.0461520.6129320.4157530.049*
H12B0.1394800.5604960.4641700.049*
H12C0.1693430.5352880.3980190.049*
C130.4476 (3)0.5458 (3)0.46822 (11)0.0264 (6)
H130.4382820.5679220.4269310.032*
C140.4986 (3)0.6556 (3)0.49942 (12)0.0413 (8)
H14A0.5819270.6786450.4831260.062*
H14B0.5091910.6370010.5401650.062*
H14C0.4376230.7219840.4950590.062*
C150.5423 (3)0.4419 (3)0.47129 (18)0.0453 (9)
H15A0.5040520.3708220.4533940.068*
H15B0.5622780.4244110.5114500.068*
H15C0.6215020.4634570.4509960.068*
C160.3151 (2)0.3971 (2)0.25267 (10)0.0171 (5)
C170.4467 (3)0.3911 (2)0.23968 (11)0.0207 (6)
C180.4805 (3)0.3365 (2)0.18834 (11)0.0270 (6)
H180.5687150.3306870.1779810.032*
C190.3877 (3)0.2906 (3)0.15223 (11)0.0293 (6)
H190.4127720.2540230.1172110.035*
C200.2586 (3)0.2971 (2)0.16641 (10)0.0266 (5)
H200.1960980.2645550.1411300.032*
C210.2193 (3)0.3511 (2)0.21743 (10)0.0205 (5)
C220.5492 (3)0.4415 (3)0.27965 (12)0.0259 (6)
H220.5037780.4841440.3114360.031*
C230.6350 (4)0.5327 (4)0.24968 (15)0.0524 (10)
H23A0.6811400.4935510.2182270.079*
H23B0.6970900.5653540.2771400.079*
H23C0.5818950.5978850.2344030.079*
C240.6274 (4)0.3407 (3)0.30637 (17)0.0595 (11)
H24A0.6795970.3018350.2767620.089*
H24B0.5690130.2816420.3234660.089*
H24C0.6837880.3735480.3360970.089*
C250.0776 (3)0.3555 (3)0.23361 (12)0.0261 (6)
H250.0688020.4101860.2673090.031*
C260.0316 (3)0.2308 (3)0.25208 (13)0.0390 (7)
H26A0.0363220.1757850.2194070.059*
H26B0.0574750.2357880.2655870.059*
H26C0.0866460.2009850.2830540.059*
C270.0068 (3)0.4051 (3)0.18560 (13)0.0375 (8)
H27A0.0252280.4841620.1740540.056*
H27B0.0955870.4124890.1992110.056*
H27C0.0040310.3505690.1527180.056*
C280.2743 (3)0.0363 (2)0.40865 (10)0.0218 (5)
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Au10.01867 (5)0.01490 (5)0.01529 (4)0.00074 (3)0.00236 (3)0.00049 (3)
O10.0479 (13)0.0154 (9)0.0502 (12)0.0026 (9)0.0055 (11)0.0016 (8)
N10.0162 (10)0.0178 (10)0.0132 (9)0.0007 (8)0.0020 (8)0.0020 (6)
N20.0162 (10)0.0153 (9)0.0137 (9)0.0017 (9)0.0004 (8)0.0009 (7)
N30.0358 (14)0.0224 (11)0.0268 (11)0.0023 (12)0.0081 (11)0.0032 (8)
C10.0122 (11)0.0174 (10)0.0148 (10)0.0004 (10)0.0013 (9)0.0008 (8)
C20.0213 (12)0.0143 (10)0.0235 (12)0.0016 (10)0.0008 (11)0.0022 (9)
C30.0213 (13)0.0164 (11)0.0192 (11)0.0002 (11)0.0006 (11)0.0034 (9)
C40.0198 (12)0.0179 (11)0.0125 (10)0.0034 (10)0.0006 (9)0.0020 (8)
C50.0163 (12)0.0209 (13)0.0208 (13)0.0043 (10)0.0011 (10)0.0030 (10)
C60.0224 (15)0.0298 (15)0.0215 (14)0.0038 (11)0.0067 (11)0.0012 (11)
C70.0326 (15)0.0326 (16)0.0149 (12)0.0032 (12)0.0035 (11)0.0016 (11)
C80.0252 (14)0.0341 (15)0.0184 (12)0.0012 (11)0.0049 (10)0.0032 (10)
C90.0204 (12)0.0225 (14)0.0194 (13)0.0002 (10)0.0014 (10)0.0016 (10)
C100.0155 (12)0.0300 (15)0.0232 (14)0.0001 (11)0.0009 (10)0.0024 (11)
C110.0345 (17)0.0296 (16)0.054 (2)0.0079 (13)0.0191 (15)0.0070 (14)
C120.0256 (15)0.0304 (16)0.0425 (17)0.0015 (12)0.0100 (13)0.0063 (13)
C130.0205 (13)0.0397 (17)0.0190 (13)0.0062 (12)0.0051 (11)0.0025 (12)
C140.046 (2)0.0443 (19)0.0339 (19)0.0176 (16)0.0041 (15)0.0028 (14)
C150.0194 (17)0.048 (2)0.068 (3)0.0007 (15)0.0118 (16)0.0029 (18)
C160.0225 (12)0.0167 (11)0.0121 (11)0.0022 (10)0.0013 (9)0.0012 (9)
C170.0229 (13)0.0197 (13)0.0194 (13)0.0014 (11)0.0024 (10)0.0015 (10)
C180.0259 (15)0.0301 (15)0.0249 (14)0.0052 (12)0.0070 (11)0.0020 (12)
C190.0391 (16)0.0325 (16)0.0163 (12)0.0090 (12)0.0028 (11)0.0049 (11)
C200.0339 (15)0.0279 (12)0.0180 (11)0.0044 (12)0.0064 (11)0.0050 (9)
C210.0233 (13)0.0205 (11)0.0176 (11)0.0015 (11)0.0019 (10)0.0014 (9)
C220.0192 (14)0.0299 (16)0.0287 (15)0.0010 (12)0.0051 (11)0.0059 (12)
C230.047 (2)0.059 (2)0.051 (2)0.027 (2)0.0122 (18)0.0087 (19)
C240.060 (2)0.047 (2)0.071 (3)0.0126 (18)0.045 (2)0.0157 (19)
C250.0215 (14)0.0371 (17)0.0198 (14)0.0017 (12)0.0026 (11)0.0029 (12)
C260.0282 (14)0.0491 (19)0.0397 (16)0.0129 (15)0.0086 (12)0.0063 (16)
C270.0280 (16)0.054 (2)0.0302 (17)0.0101 (15)0.0068 (13)0.0018 (15)
C280.0220 (13)0.0270 (14)0.0163 (12)0.0029 (12)0.0008 (11)0.0052 (9)
Geometric parameters (Å, º) top
Au1—N31.999 (2)C14—H14A0.9800
Au1—C11.963 (2)C14—H14B0.9800
O1—C281.210 (3)C14—H14C0.9800
N1—C11.360 (3)C15—H15A0.9800
N1—C21.382 (3)C15—H15B0.9800
N1—C41.447 (3)C15—H15C0.9800
N2—C11.352 (3)C16—C171.402 (4)
N2—C31.387 (3)C16—C211.390 (3)
N2—C161.443 (3)C17—C181.390 (4)
N3—C281.130 (3)C17—C221.524 (4)
C2—H20.94 (3)C18—H180.9500
C2—C31.341 (3)C18—C191.380 (4)
C3—H30.89 (2)C19—H190.9500
C4—C51.404 (3)C19—C201.384 (4)
C4—C91.388 (3)C20—H200.9500
C5—C61.395 (4)C20—C211.396 (3)
C5—C101.520 (3)C21—C251.521 (4)
C6—H60.9500C22—H221.0000
C6—C71.382 (4)C22—C231.523 (4)
C7—H70.9500C22—C241.521 (4)
C7—C81.381 (4)C23—H23A0.9800
C8—H80.9500C23—H23B0.9800
C8—C91.399 (3)C23—H23C0.9800
C9—C131.521 (4)C24—H24A0.9800
C10—H101.0000C24—H24B0.9800
C10—C111.527 (4)C24—H24C0.9800
C10—C121.532 (4)C25—H251.0000
C11—H11A0.9800C25—C261.533 (4)
C11—H11B0.9800C25—C271.527 (4)
C11—H11C0.9800C26—H26A0.9800
C12—H12A0.9800C26—H26B0.9800
C12—H12B0.9800C26—H26C0.9800
C12—H12C0.9800C27—H27A0.9800
C13—H131.0000C27—H27B0.9800
C13—C141.521 (4)C27—H27C0.9800
C13—C151.522 (4)
C1—Au1—N3178.14 (11)H14A—C14—H14C109.5
C1—N1—C2111.26 (18)H14B—C14—H14C109.5
C1—N1—C4123.35 (18)C13—C15—H15A109.5
C2—N1—C4125.36 (18)C13—C15—H15B109.5
C1—N2—C3110.91 (18)C13—C15—H15C109.5
C1—N2—C16125.33 (18)H15A—C15—H15B109.5
C3—N2—C16123.69 (18)H15A—C15—H15C109.5
C28—N3—Au1173.8 (2)H15B—C15—H15C109.5
N1—C1—Au1126.05 (16)C17—C16—N2117.5 (2)
N2—C1—Au1129.61 (16)C21—C16—N2118.8 (2)
N2—C1—N1104.26 (17)C21—C16—C17123.6 (2)
N1—C2—H2121.6 (15)C16—C17—C22122.1 (2)
C3—C2—N1106.53 (19)C18—C17—C16117.0 (2)
C3—C2—H2131.7 (15)C18—C17—C22120.8 (2)
N2—C3—H3121.3 (15)C17—C18—H18119.6
C2—C3—N2107.05 (19)C19—C18—C17120.8 (3)
C2—C3—H3131.7 (15)C19—C18—H18119.6
C5—C4—N1117.9 (2)C18—C19—H19119.6
C9—C4—N1117.9 (2)C18—C19—C20120.8 (2)
C9—C4—C5124.2 (2)C20—C19—H19119.6
C4—C5—C10121.9 (2)C19—C20—H20119.6
C6—C5—C4116.5 (2)C19—C20—C21120.7 (2)
C6—C5—C10121.5 (2)C21—C20—H20119.6
C5—C6—H6119.6C16—C21—C20117.0 (2)
C7—C6—C5120.9 (3)C16—C21—C25122.3 (2)
C7—C6—H6119.6C20—C21—C25120.6 (2)
C6—C7—H7119.6C17—C22—H22107.4
C8—C7—C6120.8 (2)C23—C22—C17112.0 (2)
C8—C7—H7119.6C23—C22—H22107.4
C7—C8—H8119.5C24—C22—C17110.6 (2)
C7—C8—C9121.0 (2)C24—C22—H22107.4
C9—C8—H8119.5C24—C22—C23111.7 (3)
C4—C9—C8116.6 (2)C22—C23—H23A109.5
C4—C9—C13122.8 (2)C22—C23—H23B109.5
C8—C9—C13120.6 (2)C22—C23—H23C109.5
C5—C10—H10107.9H23A—C23—H23B109.5
C5—C10—C11112.8 (2)H23A—C23—H23C109.5
C5—C10—C12109.8 (2)H23B—C23—H23C109.5
C11—C10—H10107.9C22—C24—H24A109.5
C11—C10—C12110.4 (2)C22—C24—H24B109.5
C12—C10—H10107.9C22—C24—H24C109.5
C10—C11—H11A109.5H24A—C24—H24B109.5
C10—C11—H11B109.5H24A—C24—H24C109.5
C10—C11—H11C109.5H24B—C24—H24C109.5
H11A—C11—H11B109.5C21—C25—H25107.7
H11A—C11—H11C109.5C21—C25—C26110.0 (2)
H11B—C11—H11C109.5C21—C25—C27112.7 (2)
C10—C12—H12A109.5C26—C25—H25107.7
C10—C12—H12B109.5C27—C25—H25107.7
C10—C12—H12C109.5C27—C25—C26110.9 (2)
H12A—C12—H12B109.5C25—C26—H26A109.5
H12A—C12—H12C109.5C25—C26—H26B109.5
H12B—C12—H12C109.5C25—C26—H26C109.5
C9—C13—H13107.2H26A—C26—H26B109.5
C9—C13—C15110.8 (2)H26A—C26—H26C109.5
C14—C13—C9112.6 (2)H26B—C26—H26C109.5
C14—C13—H13107.2C25—C27—H27A109.5
C14—C13—C15111.4 (3)C25—C27—H27B109.5
C15—C13—H13107.2C25—C27—H27C109.5
C13—C14—H14A109.5H27A—C27—H27B109.5
C13—C14—H14B109.5H27A—C27—H27C109.5
C13—C14—H14C109.5H27B—C27—H27C109.5
H14A—C14—H14B109.5N3—C28—O1179.3 (3)
N1—C2—C3—N20.1 (3)C5—C6—C7—C80.2 (4)
N1—C4—C5—C6178.5 (2)C6—C5—C10—C1140.7 (4)
N1—C4—C5—C103.9 (3)C6—C5—C10—C1282.9 (3)
N1—C4—C9—C8178.4 (2)C6—C7—C8—C90.1 (4)
N1—C4—C9—C130.5 (4)C7—C8—C9—C40.5 (4)
N2—C16—C17—C18177.2 (2)C7—C8—C9—C13178.5 (3)
N2—C16—C17—C223.0 (4)C8—C9—C13—C1451.9 (3)
N2—C16—C21—C20177.1 (2)C8—C9—C13—C1573.7 (3)
N2—C16—C21—C254.4 (3)C9—C4—C5—C61.0 (4)
C1—N1—C2—C30.2 (3)C9—C4—C5—C10176.5 (2)
C1—N1—C4—C582.3 (3)C10—C5—C6—C7177.2 (2)
C1—N1—C4—C997.3 (3)C16—N2—C1—Au16.1 (4)
C1—N2—C3—C20.0 (3)C16—N2—C1—N1177.3 (2)
C1—N2—C16—C1791.9 (3)C16—N2—C3—C2177.2 (2)
C1—N2—C16—C2190.3 (3)C16—C17—C18—C190.0 (4)
C2—N1—C1—Au1177.09 (17)C16—C17—C22—C23124.0 (3)
C2—N1—C1—N20.3 (3)C16—C17—C22—C24110.7 (3)
C2—N1—C4—C5100.1 (3)C16—C21—C25—C26105.2 (3)
C2—N1—C4—C980.3 (3)C16—C21—C25—C27130.5 (3)
C3—N2—C1—Au1176.85 (18)C17—C16—C21—C200.4 (4)
C3—N2—C1—N10.2 (3)C17—C16—C21—C25178.1 (2)
C3—N2—C16—C1784.8 (3)C17—C18—C19—C200.4 (4)
C3—N2—C16—C2192.9 (3)C18—C17—C22—C2356.1 (4)
C4—N1—C1—Au15.0 (4)C18—C17—C22—C2469.2 (4)
C4—N1—C1—N2178.2 (2)C18—C19—C20—C210.4 (4)
C4—N1—C2—C3178.1 (2)C19—C20—C21—C160.0 (4)
C4—C5—C6—C70.3 (4)C19—C20—C21—C25178.5 (2)
C4—C5—C10—C11141.9 (3)C20—C21—C25—C2673.2 (3)
C4—C5—C10—C1294.5 (3)C20—C21—C25—C2751.1 (3)
C4—C9—C13—C14130.3 (3)C21—C16—C17—C180.4 (4)
C4—C9—C13—C15104.1 (3)C21—C16—C17—C22179.4 (2)
C5—C4—C9—C81.1 (4)C22—C17—C18—C19179.8 (3)
C5—C4—C9—C13179.0 (2)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
C2—H2···O1i0.94 (3)2.25 (3)3.127 (3)155 (2)
Symmetry code: (i) x, y+1, z.
 

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