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Acta Crystallogr Sect E Struct Rep Online. 2010 April 1; 66(Pt 4): m429.
Published online 2010 March 20. doi:  10.1107/S1600536810009906
PMCID: PMC2983967

[(Z)-O-Isopropyl N-phenyl­thio­car­bam­ato-κS](tricyclo­hexyl­phosphine-κP)gold(I)

Abstract

The Au atom in the title compound, [Au(C10H12NOS)(C18H33P)], is coordinated within an S,P-donor set that defines a slightly distorted linear geometry [S—Au—P = 174.54 (2)°], with the distortion due in part to a close intra­molecular Au(...)O contact [3.1702 (16) Å]. In the crystal structure, mol­ecules are arranged into supra­molecular chains along the b axis mediated by C—H(...)O inter­actions.

Related literature

For the structural systematics and luminescence properties of phosphinegold(I) carbonimidothio­ates, see: Ho et al. (2006 [triangle]); Ho & Tiekink (2007 [triangle]); Kuan et al. (2008 [triangle]). For the synthesis, see Hall et al. (1993 [triangle]).

An external file that holds a picture, illustration, etc.
Object name is e-66-0m429-scheme1.jpg

Experimental

Crystal data

  • [Au(C10H12NOS)(C18H33P)]
  • M r = 671.65
  • Orthorhombic, An external file that holds a picture, illustration, etc.
Object name is e-66-0m429-efi1.jpg
  • a = 19.3312 (10) Å
  • b = 15.1116 (7) Å
  • c = 19.811 (1) Å
  • V = 5787.3 (5) Å3
  • Z = 8
  • Mo Kα radiation
  • μ = 5.23 mm−1
  • T = 193 K
  • 0.23 × 0.18 × 0.16 mm

Data collection

  • Bruker SMART CCD diffractometer
  • Absorption correction: multi-scan (SADABS; Bruker, 2000 [triangle]) T min = 0.544, T max = 1
  • 39425 measured reflections
  • 6645 independent reflections
  • 5481 reflections with I > 2σ(I)
  • R int = 0.040

Refinement

  • R[F 2 > 2σ(F 2)] = 0.021
  • wR(F 2) = 0.050
  • S = 1.03
  • 6645 reflections
  • 300 parameters
  • H-atom parameters constrained
  • Δρmax = 0.99 e Å−3
  • Δρmin = −0.69 e Å−3

Data collection: SMART (Bruker, 2000 [triangle]); cell refinement: SAINT (Bruker, 2000 [triangle]); data reduction: SAINT; program(s) used to solve structure: PATTY in DIRDIF92 (Beurskens et al., 1992 [triangle]); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 [triangle]); molecular graphics: ORTEP-3 (Farrugia, 1997 [triangle]) and DIAMOND (Brandenburg, 2006 [triangle]); software used to prepare material for publication: publCIF (Westrip, 2010 [triangle]).

Table 1
Selected bond lengths (Å)
Table 2
Hydrogen-bond geometry (Å, °)

Supplementary Material

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536810009906/ez2204sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536810009906/ez2204Isup2.hkl

Additional supplementary materials: crystallographic information; 3D view; checkCIF report

Acknowledgments

The National University of Singapore (grant No. R-143–000-213–112) is thanked for support.

supplementary crystallographic information

Comment

Systematic structural studies of molecules with the general formula R3PAu[SC(OR')═NR''], for R, R' and R'' = alkyl and aryl, are motivated by crystal engineering and luminescence considerations (Ho et al. 2006; Ho & Tiekink, 2007; Kuan et al., 2008), and led to the synthesis and characterisation of the title compound, (I).

The gold atom in (I) exists within an SP donor set defined by the phosphine-P and thiolate-S atoms, Table 1 and Fig. 1. The carbonimidothioate ligand is functioning as a thiolate as seen by the magnitudes of the C1—S1 [1.755 (2) Å] and C1═N1 [1.263 (3) Å] bond distances. The coordination geometry is distorted from the ideal linear [S—Au—P = 174.54 (2) °] owing to the close approach of the O1 atom [3.1702 (16) Å].

The most prominent interactions in the crystal structure are of the type C–H···O, Table 2, and these lead to the formation of supramolecular chains with glide symmetry along the b axis, Fig. 2.

Experimental

Compound (I) was prepared following the standard literature procedure from the reaction of Cy3PAuCl and (i-Pr)OC(═S)N(H)Ph in the presence of NaOH (Hall et al., 1993). Crystals were obtained by the slow evaporation of a CH2Cl2/hexane (3/1) solution held at room temperature.

Refinement

The H atoms were geometrically placed (C—H = 0.95-1.00 Å) and refined as riding with Uiso(H) = 1.2-1.5Ueq(C).

Figures

Fig. 1.
Molecular structure of (I) showing atom-labelling scheme and displacement ellipsoids at the 35% probability level.
Fig. 2.
A view of a supramolecular chain in (I) aligned along the b axis with the C–H···O interactions shown as orange dashed lines. Colour code: Au, orange; S, yellow; P, pink; O, red; N, blue; C, grey; and H, green.

Crystal data

[Au(C10H12NOS)(C18H33P)]F(000) = 2704
Mr = 671.65Dx = 1.542 Mg m3
Orthorhombic, PbcaMo Kα radiation, λ = 0.71069 Å
Hall symbol: -P 2ac 2abCell parameters from 6370 reflections
a = 19.3312 (10) Åθ = 2.3–30.0°
b = 15.1116 (7) ŵ = 5.23 mm1
c = 19.811 (1) ÅT = 193 K
V = 5787.3 (5) Å3Block, colourless
Z = 80.23 × 0.18 × 0.16 mm

Data collection

Bruker SMART CCD diffractometer6645 independent reflections
Radiation source: fine-focus sealed tube5481 reflections with I > 2σ(I)
graphiteRint = 0.040
ω scansθmax = 27.5°, θmin = 2.0°
Absorption correction: multi-scan (SADABS; Bruker, 2000)h = −25→23
Tmin = 0.544, Tmax = 1k = −19→12
39425 measured reflectionsl = −25→25

Refinement

Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.021Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.050H-atom parameters constrained
S = 1.03w = 1/[σ2(Fo2) + (0.0229P)2] where P = (Fo2 + 2Fc2)/3
6645 reflections(Δ/σ)max = 0.005
300 parametersΔρmax = 0.99 e Å3
0 restraintsΔρmin = −0.69 e Å3

Special details

Geometry. All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell s.u.'s are taken into account individually in the estimation of s.u.'s in distances, angles and torsion angles; correlations between s.u.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell s.u.'s is used for estimating s.u.'s 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 > 2σ(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)

xyzUiso*/Ueq
Au0.187999 (5)0.453847 (6)0.925784 (4)0.01954 (4)
S10.20150 (3)0.58446 (4)0.86767 (3)0.02664 (14)
P10.17856 (3)0.33212 (4)0.99177 (3)0.01871 (13)
O10.14511 (8)0.48712 (10)0.77343 (8)0.0226 (4)
N10.13197 (11)0.63489 (12)0.75576 (10)0.0248 (5)
C10.15504 (12)0.57284 (15)0.79206 (12)0.0210 (5)
C20.14430 (13)0.72399 (14)0.77403 (12)0.0233 (5)
C30.20992 (13)0.76015 (16)0.77533 (13)0.0280 (6)
H30.24890.72370.76620.034*
C40.21951 (15)0.84864 (16)0.78978 (13)0.0318 (6)
H40.26500.87260.79050.038*
C50.16365 (16)0.90265 (17)0.80318 (15)0.0376 (7)
H50.17030.96330.81400.045*
C60.09806 (16)0.86735 (16)0.80066 (16)0.0403 (7)
H60.05920.90410.80930.048*
C70.08822 (14)0.77876 (16)0.78567 (15)0.0331 (6)
H70.04270.75540.78340.040*
C80.11414 (14)0.47124 (16)0.70740 (13)0.0285 (6)
H80.07260.50990.70160.034*
C90.09212 (15)0.37553 (16)0.70929 (15)0.0360 (7)
H9A0.13300.33780.71460.054*
H9B0.06840.36050.66710.054*
H9C0.06060.36610.74740.054*
C100.16562 (18)0.4903 (2)0.65267 (16)0.0490 (8)
H10A0.18140.55170.65640.073*
H10B0.14390.48120.60850.073*
H10C0.20530.45030.65730.073*
C110.14793 (13)0.23346 (15)0.94552 (13)0.0233 (5)
H110.19040.20270.92890.028*
C120.10620 (14)0.25767 (17)0.88274 (14)0.0334 (6)
H12A0.06270.28720.89640.040*
H12B0.13300.29970.85470.040*
C130.08930 (16)0.1754 (2)0.84138 (16)0.0463 (8)
H13A0.06020.19240.80240.056*
H13B0.13270.14950.82370.056*
C140.05156 (16)0.1066 (2)0.88319 (18)0.0551 (10)
H14A0.00570.12990.89650.066*
H14B0.04410.05280.85570.066*
C150.09231 (18)0.0828 (2)0.94590 (18)0.0515 (9)
H15A0.13610.05370.93260.062*
H15B0.06540.04030.97340.062*
C160.10861 (15)0.16520 (16)0.98846 (15)0.0357 (7)
H16A0.13710.14821.02790.043*
H16B0.06500.19161.00530.043*
C170.11942 (13)0.35252 (15)1.06315 (11)0.0214 (5)
H170.11170.29541.08740.026*
C180.15046 (15)0.41908 (19)1.11282 (14)0.0356 (7)
H18A0.16200.47461.08880.043*
H18B0.19370.39471.13220.043*
C190.09894 (18)0.4387 (2)1.16965 (17)0.0554 (9)
H19A0.09140.38411.19630.066*
H19B0.11900.48381.20010.066*
C200.03053 (18)0.4714 (2)1.14351 (18)0.0548 (9)
H20A0.03710.52901.12060.066*
H20B−0.00160.48051.18180.066*
C21−0.00063 (15)0.4056 (2)1.09443 (15)0.0417 (7)
H21A−0.04410.43001.07560.050*
H21B−0.01190.35011.11850.050*
C220.04988 (13)0.38596 (17)1.03702 (13)0.0314 (6)
H22A0.02940.34081.00680.038*
H22B0.05730.44051.01030.038*
C230.26327 (12)0.30306 (15)1.02821 (12)0.0230 (5)
H230.27640.35321.05850.028*
C240.31875 (12)0.29918 (18)0.97299 (14)0.0284 (6)
H24A0.30780.25070.94110.034*
H24B0.31880.35550.94740.034*
C250.39004 (14)0.28369 (19)1.00344 (15)0.0395 (7)
H25A0.40330.33551.03110.047*
H25B0.42450.27730.96680.047*
C260.39063 (15)0.2002 (2)1.04759 (16)0.0442 (8)
H26A0.38200.14761.01900.053*
H26B0.43680.19341.06860.053*
C270.33607 (15)0.2054 (2)1.10215 (15)0.0396 (7)
H27A0.34720.25461.13330.047*
H27B0.33600.14971.12850.047*
C280.26457 (14)0.22035 (17)1.07165 (13)0.0310 (6)
H28A0.25160.16851.04380.037*
H28B0.23010.22621.10830.037*

Atomic displacement parameters (Å2)

U11U22U33U12U13U23
Au0.02220 (6)0.01907 (6)0.01734 (6)0.00080 (4)−0.00015 (4)0.00148 (3)
S10.0369 (4)0.0185 (3)0.0245 (3)−0.0044 (3)−0.0083 (3)0.0021 (2)
P10.0202 (3)0.0198 (3)0.0161 (3)−0.0002 (2)−0.0012 (2)0.0001 (2)
O10.0274 (9)0.0162 (8)0.0242 (9)−0.0010 (7)−0.0049 (8)−0.0033 (7)
N10.0287 (12)0.0197 (10)0.0259 (12)−0.0001 (9)−0.0057 (9)0.0009 (8)
C10.0187 (12)0.0212 (12)0.0232 (14)−0.0003 (10)0.0014 (10)−0.0016 (10)
C20.0310 (14)0.0197 (12)0.0192 (13)−0.0003 (10)−0.0054 (11)0.0041 (10)
C30.0295 (14)0.0298 (14)0.0247 (14)−0.0020 (11)−0.0020 (11)0.0056 (11)
C40.0358 (15)0.0314 (15)0.0281 (15)−0.0124 (12)−0.0082 (12)0.0076 (11)
C50.0568 (19)0.0167 (13)0.0392 (18)−0.0072 (13)−0.0184 (15)0.0038 (11)
C60.0405 (17)0.0220 (14)0.058 (2)0.0100 (12)−0.0093 (15)−0.0040 (13)
C70.0281 (14)0.0227 (13)0.0485 (19)0.0004 (11)−0.0079 (13)0.0015 (12)
C80.0350 (15)0.0251 (13)0.0254 (15)0.0007 (11)−0.0057 (12)−0.0045 (10)
C90.0396 (16)0.0304 (15)0.0381 (18)−0.0103 (12)−0.0052 (13)−0.0067 (12)
C100.075 (2)0.0394 (17)0.0328 (18)−0.0116 (17)0.0153 (16)−0.0100 (14)
C110.0220 (13)0.0230 (13)0.0249 (14)−0.0017 (10)0.0009 (10)−0.0061 (10)
C120.0352 (15)0.0384 (15)0.0267 (15)−0.0005 (12)−0.0072 (12)−0.0102 (12)
C130.0423 (18)0.057 (2)0.0397 (19)0.0019 (15)−0.0102 (14)−0.0255 (15)
C140.0392 (19)0.0485 (19)0.078 (3)−0.0093 (15)−0.0070 (18)−0.0400 (18)
C150.055 (2)0.0299 (16)0.070 (2)−0.0126 (15)0.0029 (18)−0.0121 (16)
C160.0400 (16)0.0259 (14)0.0412 (18)−0.0112 (12)−0.0012 (14)−0.0032 (12)
C170.0255 (13)0.0223 (12)0.0164 (13)−0.0034 (10)0.0029 (10)−0.0017 (9)
C180.0363 (16)0.0433 (16)0.0272 (16)−0.0026 (13)0.0015 (13)−0.0157 (13)
C190.056 (2)0.078 (3)0.0323 (19)−0.0080 (18)0.0096 (16)−0.0249 (16)
C200.052 (2)0.058 (2)0.054 (2)0.0009 (16)0.0267 (18)−0.0227 (16)
C210.0277 (16)0.0544 (19)0.0431 (18)0.0026 (14)0.0128 (13)−0.0054 (15)
C220.0239 (14)0.0415 (16)0.0288 (16)0.0039 (11)0.0042 (11)−0.0028 (11)
C230.0244 (13)0.0255 (13)0.0191 (13)0.0029 (10)−0.0034 (10)−0.0001 (10)
C240.0231 (14)0.0375 (15)0.0248 (14)0.0003 (11)0.0024 (11)0.0050 (11)
C250.0234 (15)0.0557 (19)0.0392 (18)0.0025 (13)0.0036 (13)−0.0005 (14)
C260.0328 (17)0.065 (2)0.0351 (18)0.0218 (15)−0.0037 (14)0.0056 (15)
C270.0382 (17)0.0500 (19)0.0305 (17)0.0164 (14)−0.0066 (14)0.0087 (13)
C280.0320 (15)0.0349 (15)0.0260 (15)0.0065 (12)−0.0016 (12)0.0091 (11)

Geometric parameters (Å, °)

Au—P12.2641 (6)C14—H14B0.9900
Au—S12.2998 (6)C15—C161.536 (4)
S1—C11.755 (2)C15—H15A0.9900
P1—C231.843 (2)C15—H15B0.9900
P1—C171.844 (2)C16—H16A0.9900
P1—C111.847 (2)C16—H16B0.9900
O1—C11.361 (3)C17—C221.527 (3)
O1—C81.458 (3)C17—C181.530 (3)
N1—C11.263 (3)C17—H171.0000
N1—C21.414 (3)C18—C191.532 (4)
C2—C31.382 (3)C18—H18A0.9900
C2—C71.383 (3)C18—H18B0.9900
C3—C41.380 (3)C19—C201.504 (5)
C3—H30.9500C19—H19A0.9900
C4—C51.379 (4)C19—H19B0.9900
C4—H40.9500C20—C211.515 (4)
C5—C61.377 (4)C20—H20A0.9900
C5—H50.9500C20—H20B0.9900
C6—C71.384 (3)C21—C221.528 (4)
C6—H60.9500C21—H21A0.9900
C7—H70.9500C21—H21B0.9900
C8—C101.500 (4)C22—H22A0.9900
C8—C91.508 (3)C22—H22B0.9900
C8—H81.0000C23—C281.518 (3)
C9—H9A0.9800C23—C241.533 (3)
C9—H9B0.9800C23—H231.0000
C9—H9C0.9800C24—C251.522 (4)
C10—H10A0.9800C24—H24A0.9900
C10—H10B0.9800C24—H24B0.9900
C10—H10C0.9800C25—C261.535 (4)
C11—C121.527 (3)C25—H25A0.9900
C11—C161.538 (3)C25—H25B0.9900
C11—H111.0000C26—C271.512 (4)
C12—C131.524 (3)C26—H26A0.9900
C12—H12A0.9900C26—H26B0.9900
C12—H12B0.9900C27—C281.525 (4)
C13—C141.517 (5)C27—H27A0.9900
C13—H13A0.9900C27—H27B0.9900
C13—H13B0.9900C28—H28A0.9900
C14—C151.515 (5)C28—H28B0.9900
C14—H14A0.9900
P1—Au—S1174.54 (2)C15—C16—C11110.0 (2)
C1—S1—Au106.46 (8)C15—C16—H16A109.7
C23—P1—C17106.88 (11)C11—C16—H16A109.7
C23—P1—C11106.67 (11)C15—C16—H16B109.7
C17—P1—C11108.45 (11)C11—C16—H16B109.7
C23—P1—Au110.38 (8)H16A—C16—H16B108.2
C17—P1—Au110.91 (8)C22—C17—C18110.2 (2)
C11—P1—Au113.27 (8)C22—C17—P1109.94 (16)
C1—O1—C8117.25 (17)C18—C17—P1111.10 (17)
C1—N1—C2120.1 (2)C22—C17—H17108.5
N1—C1—O1120.2 (2)C18—C17—H17108.5
N1—C1—S1126.33 (19)P1—C17—H17108.5
O1—C1—S1113.51 (16)C17—C18—C19110.2 (2)
C3—C2—C7118.7 (2)C17—C18—H18A109.6
C3—C2—N1122.4 (2)C19—C18—H18A109.6
C7—C2—N1118.7 (2)C17—C18—H18B109.6
C4—C3—C2120.7 (2)C19—C18—H18B109.6
C4—C3—H3119.7H18A—C18—H18B108.1
C2—C3—H3119.7C20—C19—C18112.5 (3)
C5—C4—C3120.5 (3)C20—C19—H19A109.1
C5—C4—H4119.7C18—C19—H19A109.1
C3—C4—H4119.7C20—C19—H19B109.1
C6—C5—C4119.0 (2)C18—C19—H19B109.1
C6—C5—H5120.5H19A—C19—H19B107.8
C4—C5—H5120.5C19—C20—C21110.8 (3)
C5—C6—C7120.6 (3)C19—C20—H20A109.5
C5—C6—H6119.7C21—C20—H20A109.5
C7—C6—H6119.7C19—C20—H20B109.5
C2—C7—C6120.5 (2)C21—C20—H20B109.5
C2—C7—H7119.8H20A—C20—H20B108.1
C6—C7—H7119.8C20—C21—C22110.6 (2)
O1—C8—C10110.2 (2)C20—C21—H21A109.5
O1—C8—C9104.6 (2)C22—C21—H21A109.5
C10—C8—C9112.9 (2)C20—C21—H21B109.5
O1—C8—H8109.7C22—C21—H21B109.5
C10—C8—H8109.7H21A—C21—H21B108.1
C9—C8—H8109.7C17—C22—C21112.0 (2)
C8—C9—H9A109.5C17—C22—H22A109.2
C8—C9—H9B109.5C21—C22—H22A109.2
H9A—C9—H9B109.5C17—C22—H22B109.2
C8—C9—H9C109.5C21—C22—H22B109.2
H9A—C9—H9C109.5H22A—C22—H22B107.9
H9B—C9—H9C109.5C28—C23—C24111.2 (2)
C8—C10—H10A109.5C28—C23—P1115.66 (18)
C8—C10—H10B109.5C24—C23—P1110.57 (17)
H10A—C10—H10B109.5C28—C23—H23106.3
C8—C10—H10C109.5C24—C23—H23106.3
H10A—C10—H10C109.5P1—C23—H23106.3
H10B—C10—H10C109.5C25—C24—C23110.9 (2)
C12—C11—C16110.5 (2)C25—C24—H24A109.5
C12—C11—P1112.33 (17)C23—C24—H24A109.5
C16—C11—P1115.17 (18)C25—C24—H24B109.5
C12—C11—H11106.0C23—C24—H24B109.5
C16—C11—H11106.0H24A—C24—H24B108.1
P1—C11—H11106.0C24—C25—C26111.0 (2)
C13—C12—C11110.8 (2)C24—C25—H25A109.4
C13—C12—H12A109.5C26—C25—H25A109.4
C11—C12—H12A109.5C24—C25—H25B109.4
C13—C12—H12B109.5C26—C25—H25B109.4
C11—C12—H12B109.5H25A—C25—H25B108.0
H12A—C12—H12B108.1C27—C26—C25111.1 (2)
C14—C13—C12111.6 (2)C27—C26—H26A109.4
C14—C13—H13A109.3C25—C26—H26A109.4
C12—C13—H13A109.3C27—C26—H26B109.4
C14—C13—H13B109.3C25—C26—H26B109.4
C12—C13—H13B109.3H26A—C26—H26B108.0
H13A—C13—H13B108.0C26—C27—C28110.9 (2)
C15—C14—C13111.1 (2)C26—C27—H27A109.5
C15—C14—H14A109.4C28—C27—H27A109.5
C13—C14—H14A109.4C26—C27—H27B109.5
C15—C14—H14B109.4C28—C27—H27B109.5
C13—C14—H14B109.4H27A—C27—H27B108.1
H14A—C14—H14B108.0C23—C28—C27111.2 (2)
C14—C15—C16111.4 (3)C23—C28—H28A109.4
C14—C15—H15A109.4C27—C28—H28A109.4
C16—C15—H15A109.4C23—C28—H28B109.4
C14—C15—H15B109.4C27—C28—H28B109.4
C16—C15—H15B109.4H28A—C28—H28B108.0
H15A—C15—H15B108.0
P1—Au—S1—C1−165.2 (2)C14—C15—C16—C11−56.7 (3)
S1—Au—P1—C23−58.3 (3)C12—C11—C16—C1556.9 (3)
S1—Au—P1—C1759.9 (3)P1—C11—C16—C15−174.5 (2)
C2—N1—C1—O1−177.9 (2)C23—P1—C17—C22174.41 (17)
C2—N1—C1—S11.6 (4)C11—P1—C17—C22−70.93 (19)
C8—O1—C1—N16.6 (3)Au—P1—C17—C2254.05 (18)
C8—O1—C1—S1−173.04 (17)C23—P1—C17—C1852.1 (2)
Au—S1—C1—N1157.6 (2)C11—P1—C17—C18166.76 (18)
Au—S1—C1—O1−22.86 (18)Au—P1—C17—C18−68.26 (19)
C1—N1—C2—C364.9 (3)C22—C17—C18—C1954.9 (3)
C1—N1—C2—C7−120.5 (3)P1—C17—C18—C19177.0 (2)
C7—C2—C3—C41.8 (4)C17—C18—C19—C20−56.2 (4)
N1—C2—C3—C4176.4 (2)C18—C19—C20—C2156.6 (4)
C2—C3—C4—C50.0 (4)C19—C20—C21—C22−55.6 (4)
C3—C4—C5—C6−1.2 (4)C18—C17—C22—C21−56.1 (3)
C4—C5—C6—C70.7 (4)P1—C17—C22—C21−178.89 (18)
C3—C2—C7—C6−2.3 (4)C20—C21—C22—C1756.3 (3)
N1—C2—C7—C6−177.1 (2)C17—P1—C23—C2861.4 (2)
C5—C6—C7—C21.0 (4)C11—P1—C23—C28−54.4 (2)
C1—O1—C8—C1073.4 (3)Au—P1—C23—C28−177.88 (16)
C1—O1—C8—C9−165.0 (2)C17—P1—C23—C24−171.08 (17)
C23—P1—C11—C12−146.24 (18)C11—P1—C23—C2473.06 (19)
C17—P1—C11—C1299.0 (2)Au—P1—C23—C24−50.38 (18)
Au—P1—C11—C12−24.6 (2)C28—C23—C24—C25−55.4 (3)
C23—P1—C11—C1686.1 (2)P1—C23—C24—C25174.72 (18)
C17—P1—C11—C16−28.7 (2)C23—C24—C25—C2655.2 (3)
Au—P1—C11—C16−152.29 (16)C24—C25—C26—C27−56.2 (3)
C16—C11—C12—C13−56.7 (3)C25—C26—C27—C2856.4 (3)
P1—C11—C12—C13173.13 (19)C24—C23—C28—C2755.9 (3)
C11—C12—C13—C1456.0 (3)P1—C23—C28—C27−176.94 (19)
C12—C13—C14—C15−55.4 (3)C26—C27—C28—C23−56.6 (3)
C13—C14—C15—C1656.0 (4)

Hydrogen-bond geometry (Å, °)

D—H···AD—HH···AD···AD—H···A
C4—H4···O1i0.952.483.367 (3)156

Symmetry codes: (i) −x+1/2, y+1/2, z.

Footnotes

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: EZ2204).

References

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