Structure–property relationship of a complex photoluminescent arylacetylide-gold(I) compound. I: a pressure-induced phase transformation caught in the act

A pressure-induced triclinic-to-monoclinic phase transition has been caught `in the act' over a wider series of high-pressure synchrotron diffraction experiments conducted on a large, photoluminescent organo-gold(I) compound. Here, we describe the mechanism of this single-crystal-to-single-crystal phase transition, the onset of which occurs at ∼0.6 GPa, and we report a high-quality structure of the new monoclinic phase, refined using aspherical atomic scattering factors. Our case illustrates how conducting a fast series of diffraction experiments, enabled by modern equipment at synchrotron facilities, can lead to overestimation of the actual pressure of a phase transition due to slow transformation kinetics.

1. Introduction

Application of increased pressure provides a unique means of control over the intermolecular interactions in crystals without changing the chemical composition (Valiente et al., 2016). This in turn opens possibilities to discover new solid phases and construct phase diagrams of various substances (Ravindran et al., 2019; Tse, 2020; Vervoorts et al., 2021) but also to systematically study properties of materials such as photoluminescence (Li et al., 2022; Tong et al., 2022; Zou et al., 2024).

With the recent advent of fourth-generation synchrotron sources, pixel-counting detectors, membrane diamond anvil cells (DACs) and dynamic compression systems, high-pressure research at large facilities has become ever faster, more comprehensive and more efficient (Donath et al., 2023; Poręba et al., 2022; Pascarelli et al., 2023). Strong incident beams coupled with automated pressure control offer full single-crystal X-ray diffraction datasets in a couple of minutes (Guńka et al., 2021; Ambach et al., 2024), opening the possibility of tracking time-resolved processes (phase transitions or solid state reactions) hitherto only available for powder diffraction studies on simple, highly symmetric inorganic compounds (Husband et al., 2021; Ricks et al., 2024). Though such rapid nature of data collection is certainly welcome, it nevertheless demands heightened awareness about the kinetics of investigated materials.

A thorough review by Chandra Shekar & Rajan (2001) highlighted the impact of the pressurization rate on the actual path of oncoming phase transitions. Recent specific cases of inorganic materials (Husband et al., 2021; Ricks et al., 2024) as well as, on a different time scale, certain molecular crystals (Fisch et al., 2015; Zhang et al., 2021; Tchoń et al., 2021; Yuan et al., 2022) confirm that slow pressurization can result in very different transformation paths and observed phases. Most importantly, certain pressure-induced phase transitions characterized by slow kinetics may require hours, days or weeks to take place, and thus remain unobserved over the course of a rapid series of diffraction experiments (Szafrański & Katrusiak, 2017; Szafrański et al., 2021).

As a part of our ongoing project aimed at relating crystal structures to physical properties in arylacetylide-gold(I) compounds, with a particular goal of elucidating the extent to which the crystal environment can affect their photoluminescence, we turned our attention to (pyren-1-oylacetylide)(triethylphosphine)gold(I). The compound is already known to produce at least two distinct crystalline materials, which differ in ligand arrangement, the presence/absence of the aurophilic interactions and photoemission properties (Głodek et al., 2018). Its crystal form, originally named 1a′, here denoted pyrEt-α, which could be represented as (pyren-1-oylacetylide)₂Au⋯Au(triethylphosphine)₂, is the focus of the current study due to the presence of aurophilic interactions. We conducted a few series of X-ray diffraction experiments with the aim of structure determination of this moderately luminescent material over a pressure range from 1 atm to 9.00 GPa and independently at temperatures from 90 to 300 K. These structural studies will be published separately together with the variable-pressure and variable-temperature analysis of the material's photoemission, putting the latter in a wider perspective. Here we focus exclusively on the occurrence and the mechanism of a particular single-crystal-to-single-crystal (SCSC) pressure-induced phase transition occurring at a relatively low pressure of approximately 0.6 GPa. Our goal was to highlight how such transition can be tracked by means of single-crystal X-ray diffraction (SCXRD) even for a relatively large metal–organic system.

2. Experimental

2.1. Single-crystal X-ray diffraction experiments

The crystals of pyrEt-α were obtained according to the formerly published protocol (Głodek et al., 2018). The structure of pyrEt-α has been redetermined under standard atmospheric conditions to serve as a reference for high-pressure studies. SCXRD data were collected using an in-house Rigaku Oxford Diffraction SuperNova four-circle diffractometer equipped with an Eos CCD detector and a molybdenum microsource (Mo Kα, λ = 0.71 Å). The single-crystalline block was mounted on a Mitegen loop with a small amount of Paratone-N oil. Data collection and reduction were performed in CrysAlisPro (Rigaku Oxford Diffraction, 2019). Shape based absorption corrections were applied using the same software.

2.1.1. Variable-pressure experiments

High-pressure SCXRD experiments were conducted at the ESRF ID15B synchrotron beamline (λ = 0.41 Å), beam size 4 × 4 µm, equipped with either Mar555 flat-panel amorphous Se detector (series I and multi-crystal approach) or EIGER2 X CdTe 9M detector (series II). The instrument model was calibrated with an Si NIST640b calibrant and a single crystal of vanadinite with known lattice constants.

The goal of the `serial experiments' was to observe the diffraction pattern in a wide pressure range. Thin plate-like single-crystal specimens were placed in a symmetric membrane DAC of BX90-type using helium gas as a pressure-transmitting medium (PTM) (further details provided in Section S1 of the supporting information). The pressure was increased using a PACE6000 controller and verified in situ with reference ruby spectra (nominal estimated standard deviation on pressure determination 0.03 GPa). In the first series (I), four crystal specimens were placed in the DAC to gain better data coverage and compensate for radiation damage. These yielded a total of 29 useful datasets in the pressure range from 0.25 (3) to 9.03 (3) GPa, two of which, at a pressure of 0.60 (3) (crystal 2) and 0.65 (3) GPa (crystal 3) accordingly, will be commented on in more detail here. In the second series (II), a single-crystal specimen (crystal 4) yielded a total of 16 useful datasets in the pressure range from 0.25 (3) to 5.98 (3) GPa, two of which were collected 20 min apart at the same pressure of 0.82 (3) GPa.

2.1.2. Multicrystal approach

In order to increase the reciprocal space coverage for the new phase being investigated and facilitate unrestrained refinement of its crystal structure, a total of five larger pieces cut out of a single crystal (crystal 5) of pyrEt were placed in a single DAC of a Merrill–Basset (MB) design in distinct orientations. The latter type of DAC provided a larger opening angle and easier loading, but as a trade-off it did not allow for gaseous PTM use. Paratone-N oil was used as a PTM, being the only liquid PTM on site that would not dissolve the compound under investigation. Initial rapid pressurization yielded 1.10 (3) GPa within the quasi-hydrostatic limit of the applied PTM (Klotz et al., 2009; Tateiwa & Haga, 2009). Diffraction data were collected within 2 h of reaching this pressure. Data collection for each crystal specimen in each experimental series consisted of a single ϕ-scan in ± opening angle range (32 or 39° for membrane DAC and MB DAC, accordingly) with an angular step Δω of 0.5° and an exposure time of 1 s per frame. Each data collection took less than 5 min.

Data reduction was performed in CrysAlisPro (Rigaku Oxford Diffraction, 2019). Final datasets from the three largest pieces in the multi-crystal approach were merged using SORTAV, yielding the total data completeness of 71% up to a 0.65 Å resolution.

2.1.3. Structure solution and refinement

Structures were solved using SXELXS/SHELXT and refined in SHELXL (Sheldrick, 2015) within the Olex2 graphical environment (Dolomanov et al., 2009; Bourhis et al., 2015). The hydrogen atom positions were constrained to their closest carbons and had their atomic displacement parameters defined using the riding approximation. In the case of the multi-crystal approach, no further restraints or constraints were necessary. In the cases of limited data coverage (i.e. datasets collected with a membrane DAC), a number of chemically viable geometrical similarity restraints on C—C distances and atomic displacement parameters were applied during structure refinement.

The structure of the new monoclinic pyrEt-α phase at 1.10 (3) GPa was finally subjected to the Hirshfeld atom refinement (HAR) using NoSpherA2, an implementation of non-spherical atomic form factors in Olex2 (Kleemiss et al., 2021). The electron density was calculated from a Gaussian basis set single-determinant SCF wavefunction for a fragment covering twice the monoclinic asymmetric unit in the exact experimental geometry. Calculations were performed with ORCA (version 5.0; Neese et al., 2020) using the DFT approach with R2SCAN functional, x2c-TZVP basis set and DKH2 relativistic correction. The hydrogen atom positions remained constrained using the riding approximation. Molecular graphics were prepared using either Olex2 or Mercury software (version 4.3; Macrae et al., 2008). The data were deposited with the CCDC and assigned the deposition numbers 2360104, 2360105, 2360125 and 2360126.

3. Results and discussion

3.1. Structure of pyrEt-α at room temperature

In the originally published phase determined at 100 K, the triclinic crystal structure of pyrEt-α is based on a four-Au-atom-long rod [Fig. 1(a)]. The rods arrange along the [010], almost forming an infinite Au⋯Au chain in that direction, as described previously (Głodek et al., 2018). Aurophilic interactions within the rod are quite short, whereas the distance between gold atoms from subsequent rods is over 4.4 Å, easily exceeding the sum of their van der Waals radii (3.4 Å). This general arrangement is retained at room temperature, with one important difference. Instead of two adjacent, distinct and perfectly ordered Au⋯Au chains, there is only one chain, with a disorder in the position of Au4 and the connected –PEt₃ ligands. As a consequence, the room-temperature phase features a halved unit-cell parameter a compared with the 100 K conditions (Fig. S2 of the supporting information).

Figure 1 (a) Main building block of the crystal structure of pyrEt at 300 K: a rod of four Au atoms, disordered over two positions along its long axis. Atoms Au4 and Au4′ with their phosphine ligands represent the two alternative disorder variants, as the rod can begin at either `side' along the [010] crystallographic direction. The parts with 50% occupancy are represented as semi-transparent. The atomic displacement parameters are presented exclusively for atoms from the asymmetric unit at 50% probability. Hydrogen atoms have been omitted for clarity. (b) Two distinct conformations of the –PEt3 group present in this structure, viewed along (top) and perpendicular to (bottom) the Au—P bond.

Note that the conformations of the triethylphosphine ligands at atoms Au2 and Au4 are distinct. They can be classified according to Orpen et al. (1998) and later Ellis et al. (2009) as F and G, accordingly [Fig. 1(b)]. Conformation F is the most commonly observed in the CCDC and features the lowest energy when considered individually (De Silva et al., 2015). Conformation G is decidedly less energetically advantageous and rarer, though it has been observed in certain Au(I) compounds (Ellis et al., 2009; De Silva et al., 2015).

3.2. Evolution of unit-cell parameters and assigning critical pressure for phase transition

The phase transition from the triclinic space group P1 to monoclinic P2₁/c is indicated at 0.65 (3) GPa in series I and 0.82 (3) GPa in series II (Fig. 2, top). All crystal specimens in the multi-crystal approach at 1.10 (3) GPa showed monoclinic unit-cell metrics and a systematic extinction pattern consistent with the presence of a c_[010] glide plane. The diffraction data from series I, collected with an amorphous Se detector at approximately 0.60 (3) GPa, were of noticeably lower resolution and generally too weak to permit an ab initio structure solution. This data inferiority, initially attributed to radiation damage, could stem from an ongoing structural reorganization of the crystal structure.

Figure 2 (Top) Evolution of the unit-cell volume of pyrEt-α with pressure. Data points referred to more specifically in this manuscript were highlighted and labeled with the crystallite number, according to Table 1. (Bottom) Graphical representation of the unit-cell-parameter contraction with pressure, represented as a normalized fraction of reference ambient-condition values on a ChARd plot. Each triangle represents one measured unit cell, complementing a single volume point shown on the left. The uncertainties on both graphs are negligible, not exceeding the point size on the left.

In order to illustrate the phase transition, unit-cell lengths a, b and c from individual experiments were normalized to the ambient-pressure reference and plotted in a radial coordinate system (Fig. 2, bottom). This approach was recently proposed by Kaźmierczak et al. (2021) and implemented in matplotlib for the purpose of this work (Tchoń, 2024). It allowed us to identify the 0.60 GPa series I data point collected on crystal 2 as an outlier on account of a skewed a:b:c ratio, deviating from both the triclinic and the monoclinic phases. Coupled with a streaky appearance of the diffraction spots (Fig. 3), it suggests that the sample was already undergoing the phase transition during the experiment. The dataset from crystal 2 in the same DAC collected 30 min later and at a slightly higher noted pressure of 0.65 (3) GPa indicated unambiguous monoclinic unit-cell metrics.

Figure 3 Reconstructions of selected reciprocal layers from datasets flanking the aP → mP phase transition from series I (i.e. crystals 2 and 3, upper row), and series II (i.e. crystal 4) before and after a 20 min interval (lower row). Red circles indicate where reflections expected for a given cell setting are missing. The patterns on the left index unambiguously in the triclinic unit cell, the patterns on the right in the monoclinic unit cell.

A pressurization sequence in the experimental series II yielded data points closest to the expected phase transition at 0.49 (3) and 0.82 (3) GPa. The dataset at the lower pressure indicated unambiguous triclinic symmetry. At higher pressure, the first dataset indicated also unequivocally a triclinic system, and the triclinic structure could be successfully refined based on this dataset starting from the room-temperature model (Table 1). A second dataset, collected within 20 min of the first from the same crystal specimen, yielded a pattern with monoclinic symmetry (Fig. 3) and allowed for ab initio structure solution in the monoclinic space group P2₁/c. This result has been corroborated by the model obtained from unrestricted structure solution and refinement against high-coverage multi-crystal data collected at 1.10 (3) GPa.

Table 1
Summary of the experiments performed for pyrEt-α (C₂₅H₂₄AuOP, 568.38 g mol⁻¹) under atmospheric conditions and pressure points flanking the phase transition

All experiments were performed at room temperature. The larger uncertainties and the missing structure-refinement statistics in series I result from the overall worse data quality; no structures could be refined for these series.

	In house 300 K	I		II		ESRF multicrystal
	Crystal 1	Crystal 2	Crystal 3	Crystal 4	Crystal 4	Crystal 5†
DAC	–	Membrane	Membrane	Membrane	Membrane	MB
PTM	–	He	He	He	He	Paratone
Pressure (GPa)	0.00001	0.60 (3)	0.65 (3)	0.82 (3)	0.82 (3)	1.10 (3)
a (Å)	16.0839 (5)	15.905 (8)	16.116 (15)	15.906 (7)	16.13 (4)	16.0966 (4)
b (Å)	14.2240 (7)	13.294 (18)	6.7243 (18)	13.677 (2)	6.7304 (9)	6.62840 (13)
c (Å)	10.1393 (3)	9.710 (6)	18.10 (7)	9.7733 (14)	18.096 (3)	17.9473 (14)
α (°)	109.816 (4)	110.32 (9)	90	109.591 (15)	90	90
β (°)	98.398 (2)	97.79 (5)	97.9 (2)	98.20 (2)	97.93 (8)	97.886 (6)
γ (°)	85.874 (3)	86.25 (7)	90	86.14 (3)	90	90
V (Å^3)	2158.26 (15)	1907 (3)	1943 (8)	1982.2 (10)	1945 (5)	1896.77 (16)
Z, Z′	4, 2	4, 2	4, 1	4, 2	4, 1	4, 1
Space group	P1	P1	P21/c	P1	P21/c	P21/c
ρcalc (g cm^−3)	1.749	1.980	1.943	1.905	1.941	1.990
Wavelength (Å)	0.71073	0.41097	0.41097	0.41004	0.41004	0.41097
Unique reflections	13173	3412	1310	3120	2004	3932
Rint	0.031	0.239	0.198	0.046	0.163	0.059
Resolution (Å)	0.70	0.51	0.79	0.56	0.56	0.59
Completeness	0.998	0.239	0.292	0.254	0.306	0.714
Reflections, restraints, parameters	42542, 32, 603	NA	NA	4078, 279, 263	3884, 632, 235	3932, 0, 256
R1 [I> 2σ(I)]	0.039	NA	NA	0.122	0.172	0.055
wR2 [I> 2σ(I)]	0.071	NA	NA	0.271	0.374	0.174
R1 (all data)	0.070	NA	NA	0.324	0.411	0.079
wR2 (all data)	0.081	NA	NA	0.367	0.483	0.229
Δρmin/max (eÅ^−3)	−1.472/1.011	NA	NA	−0.772/1.088	−0.910/1.145	−2.104/2.432

†Three distinctly oriented pieces of the same single crystal.

Based on these observations, the actual onset of a pressure-induced phase transition can be pinpointed at ∼0.6 GPa. Pressurizing to about that point apparently pushed crystal 2 into a metastable state. Rapid data collection at the synchrotron allowed us to capture this state. In series II, rapid pressurization to ∼0.82 GPa appeared to `freeze' crystal 4 in the triclinic phase with an un-contracted unit cell for the duration of data collection. Transformation to the monoclinic phase occurred in the next 20 min, leading to an apparently stable structure with a slightly contracted (i.e. more thermodynamically favorable) unit-cell volume.

3.3. Structural changes on phase transition

The phase transformation discovered can be categorized as displacive, yet it is accompanied by substantial structural changes. The appearance of the 2₁ axis and c plane lowers the number of symmetry-independent pyrenyl and triethylphosphine moieties from 2 to 1 while preserving four pyrEt units per unit cell. Although the π-stacking arrangement of the pyrenyl moieties is retained, the inter-planar pyrene–pyrene distance becomes fixed at 1/2|b|. This new arrangement requires the pyrene moieties to recline away from [010] by 15°, making them almost perpendicular to the axis. The entire rotation can be viewed as lifting the adjacent columns along [010], bending the α angle to exactly 90° (Fig. 4).

Figure 4 Overlay of crystal structures at 0.82 (3) GPa: triclinic (blue) and monoclinic (orange); conformational changes related to phase transitions are indicated with arrows. (a) Molecular motif of a 4Au rod. (b) Close-up of the Au⋯Au interactions; disorder of the Au4 atom from the triclinic system is being resolved. (c) Conformational change in the triethylphosphine leads to less steric hindrance in the [101] direction in the crystal lattice.

In addition to the pyrene ring rotation, concerted rotations of a single ethyl group in adjacent molecular layers, analogous to formerly described motions for other metal–organic compounds, are observed (Makal, 2018). They reduce the inter-layer steric hindrance, leading to the relative shifts of layers in [101] direction. The conformation of all –PEt₃ moieties switches from mixed F/G to uniformly G, rendering the new phase perfectly ordered.

Notably, though not unexpectedly (Wuttke et al., 2018), the aurophilic interactions have the smallest impact in dictating the transformation. All gold atoms in the new P2₁/c phase are located at inversion centers and evenly spaced along b, rendering the new phase fully polymeric. There is no tendency to preserve the shorter Au⋯Au contacts, as the average Au⋯Au distance within a `rod' increases from 3.228 (6) to 3.365 (6) Å.

In the new crystal setting, the crystallographic direction [010] spanned by the Au⋯Au rods is preserved, but the length of the associated lattice vector b becomes halved. To accommodate the new symmetry, the [100] direction becomes perpendicular to [010], but otherwise undergoes little change. The new lattice vector c remains parallel to the pyrene plane but doubles in length and deviates from the original triclinic [001] by almost 30° (Figs. 4 and S2.1 of the supporting information).

The new higher-symmetry phase of pyrEt-α is a much more promising subject in the context of studying the structure–luminescence relationship. There remains just one variant of pyrene π-stacking and one variant of aurophilic interactions, both restricted by symmetry and bound with the b lattice constant. Nevertheless, our preliminary observations indicate that, while pyrEt-α displays significant pressure-induced red-shift in photoemission, the trend is not affected by the structural changes at ∼0.6 GPa. Detailed analysis of pyrEt-α luminescence as a function of temperature and pressure will be the subject of another publication.

3.4. Unrestrained crystal structure of pyrEt-α in the high-pressure phase

Crystal structure analysis under high pressure is particularly challenging for low-symmetry systems due to poor data coverage, which for a single crystal from a monoclinic system – most common in the Cambridge Structural Database (CSD) – may typically be well below 50%. This can hinder structure solution and bias the resulting crystal model, causing, for example, systematic shortening of certain bond lengths, necessitating the use of numerous constraints and strong restraints.

Among all the metal–organic structures determined at increased pressure and deposited in the CSD (Groom et al., 2016) in the last four years, the typical data coverage for orthorhombic or lower symmetry systems is ∼40% up to the IUCr resolution limit of 0.82 Å (Spek, 2020) and only 12 structures among those contain more than 25 non-hydrogen atoms in the asymmetric unit.

In the context of our structure determination for pyrEt-α, the monoclinic phase is a positive outlier. The coverage obtained for a merged dataset was over 70% up to 0.65 Å, which allowed for unrestrained refinement of parameters pertaining to non-hyrogen atoms, yielding highly reliable molecular geometry. Using aspherical atomic scattering factors in the HAR approach proved to be fully justified, lowering the total discrepancy factor by over 2%. To the best of our knowledge, this is the largest low-symmetry system investigated structurally with quantum-crystallography tools.

4. Conclusions

We have successfully characterized a particular pressure-induced symmetry-increasing SCSC phase transition occurring in the crystal structure of a large metalorganic gold(I) compound (pyrEt) in its α crystal form by means of SCXRD. The modern instrumentation at the synchrotron facility have made it possible to collect (in series I) diffraction datasets confirming the coexistence of triclinic and monoclinic phases in two separate crystallites and with evident signs of increased strain, as a result, insufficient for structure determination. In another series (II), a similar experimental setup with a hybrid-pixel detector made it possible to collect two datasets from the same single-crystal specimen, with a 20 min delay, which allowed the structure determination of first pre-transition metastable triclinic and then post-transition stable monoclinic structures at the same pressure. As a result, details of pre- and post-transition structures and the steps necessary for structural reorganization could be captured for a large and labile compound at the moment of structural transformation.

Moreover, the structure of the new monoclinic phase was confirmed by data collected at 1.10 (3) GPa from multiple crystal specimens. A high-coverage merged dataset allowed unrestrained structure refinement with an aspherical atomic scattering factor formalism for this relatively large (>50 atoms per asymmetric unit) heavy-metal-containing organometallic compound.

The short span and quick succession of subsequent experiments that enabled us to observe the phase transition can yet be detrimental when it does not grant the crystal enough time to undergo a structural transformation. This puts in a different light the studies where certain phase transitions were theoretically predicted to occur at significantly lower pressures than reported based on XRD studies (Ukita et al., 2016). Our example highlights how conceivable it is that in modern studies the experimentally determined phase-transition pressure can be sometimes overestimated, owing to the sparse sampling or rapid succession of subsequent diffraction experiments. A transition with particularly slow kinetics might even be totally overlooked. Ignoring the kinetics of a phase transformation would thus have serious consequences wherever the results of in-house diffraction experiments, typically spanning hours, were confronted with the outcomes of rapid synchrotron data collections, done in minutes. More importantly, it can have serious ramifications where parallel studies by X-ray and neutron diffraction have to be applied. With the recent advent in tools enabling high-pressure structural research with neutrons (Haberl et al., 2023), the incompatibility of results may concern studies of ice, methane clathrates or metal superhydrides, as well as a number of magnetic materials consisting of large molecular building blocks. Our parting recommendation would be to perform repeated data collections at selected pressures, providing intervals of at least a few minutes, to detect the signs of potential transformations.

Supporting information

Computing details

(crystal_1)

Crystal data

0.25(C100H96Au4O4P4)	Z = 4
Mr = 568.38	F(000) = 1104
Triclinic, P1	Dx = 1.749 Mg m^−3
a = 16.0839 (5) Å	Mo Kα radiation, λ = 0.71073 Å
b = 14.2240 (7) Å	Cell parameters from 11269 reflections
c = 10.1393 (3) Å	θ = 3.1–27.9°
α = 109.816 (4)°	µ = 6.90 mm^−1
β = 98.398 (2)°	T = 293 K
γ = 85.874 (3)°	Plate, clear light yellow
V = 2158.26 (15) Å^3	0.29 × 0.21 × 0.11 mm

Data collection

SuperNova, Single source at offset, Eos diffractometer	9022 reflections with I > 2σ(I)
Detector resolution: 8.0013 pixels mm^-1	Rint = 0.031
ω scans	θmax = 30.5°, θmin = 3.1°
Absorption correction: multi-scan CrysAlisPro 1.171.38.43c (Rigaku Oxford Diffraction, 2015) Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm.	h = −22→22
Tmin = 0.831, Tmax = 1.000	k = −20→20
42542 measured reflections	l = −14→14
13173 independent reflections

Refinement

Refinement on F^2	32 restraints
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F^2 > 2σ(F^2)] = 0.040	H-atom parameters constrained
wR(F^2) = 0.082	w = 1/[σ^2(Fo^2) + (0.024P)^2 + 1.6049P] where P = (Fo^2 + 2Fc^2)/3
S = 1.03	(Δ/σ)max = 0.002
13173 reflections	Δρmax = 1.01 e Å^−3
603 parameters	Δρmin = −1.47 e Å^−3

Special details

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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Ų)

	x	y	z	Uiso*/Ueq	Occ. (<1)
Au2	0.5000	1.0000	0.5000	0.05348 (7)
Au1	0.49819 (2)	0.76965 (2)	0.51597 (2)	0.06113 (6)
P1	0.58216 (6)	0.95252 (8)	0.31846 (10)	0.0506 (2)
O2	0.71550 (19)	0.9036 (3)	0.9898 (3)	0.0917 (11)
C85	0.5250 (3)	0.9521 (4)	0.1502 (4)	0.0684 (12)
H85A	0.5113	1.0206	0.1547	0.082*
H85B	0.5611	0.9236	0.0770	0.082*
O1	0.32491 (19)	0.6219 (3)	0.0142 (3)	0.1046 (13)
C19	0.4083 (3)	0.7236 (3)	0.3550 (5)	0.0641 (11)
C34	0.8091 (3)	0.8406 (3)	0.6701 (4)	0.0571 (10)
H34	0.7583	0.8314	0.6109	0.069*
C81	0.6689 (3)	1.0339 (3)	0.3477 (4)	0.0642 (11)
H81A	0.7022	1.0069	0.2701	0.077*
H81B	0.6467	1.0988	0.3463	0.077*
C22	0.8862 (2)	0.8655 (3)	0.9027 (4)	0.0470 (8)
C38	0.6527 (3)	0.8361 (3)	0.7598 (5)	0.0652 (11)
C39	0.5923 (3)	0.8113 (3)	0.6723 (5)	0.0635 (11)
C18	0.3554 (3)	0.6943 (3)	0.2541 (4)	0.0650 (11)
C1	0.2072 (2)	0.6509 (3)	0.1404 (4)	0.0499 (9)
C23	0.8943 (3)	0.8763 (3)	1.0501 (4)	0.0567 (9)
H23	0.8460	0.8785	1.0915	0.068*
C21	0.8089 (2)	0.8563 (3)	0.8132 (4)	0.0501 (9)
C3	0.1558 (3)	0.6208 (3)	−0.1173 (4)	0.0643 (11)
H3	0.2103	0.6210	−0.1375	0.077*
C32	0.9599 (3)	0.8489 (3)	0.6982 (4)	0.0565 (9)
C82	0.7263 (3)	1.0479 (4)	0.4860 (5)	0.0909 (16)
H82A	0.6937	1.0723	0.5635	0.136*
H82B	0.7685	1.0953	0.4967	0.136*
H82C	0.7528	0.9851	0.4850	0.136*
C37	0.7251 (2)	0.8669 (3)	0.8654 (4)	0.0595 (10)
C36	1.0416 (2)	0.8709 (3)	0.9309 (4)	0.0541 (9)
C25	1.0460 (3)	0.8827 (3)	1.0746 (5)	0.0604 (10)
C83	0.6274 (3)	0.8284 (4)	0.2983 (6)	0.0865 (16)
H83A	0.6469	0.8257	0.3922	0.104*
H83B	0.5825	0.7810	0.2575	0.104*
C17	0.2980 (3)	0.6538 (3)	0.1274 (4)	0.0619 (10)
C24	0.9697 (3)	0.8835 (3)	1.1305 (4)	0.0622 (11)
H24	0.9719	0.8891	1.2250	0.075*
C14	0.1871 (3)	0.6667 (3)	0.2761 (4)	0.0630 (11)
H14	0.2297	0.6803	0.3522	0.076*
C35	0.9620 (2)	0.8616 (3)	0.8435 (4)	0.0494 (8)
C2	0.1425 (2)	0.6338 (3)	0.0253 (4)	0.0512 (9)
C33	0.8825 (3)	0.8382 (3)	0.6134 (4)	0.0655 (11)
H33	0.8802	0.8294	0.5178	0.079*
C12	0.0405 (3)	0.6464 (3)	0.1900 (6)	0.0736 (14)
C26	1.1248 (3)	0.8911 (3)	1.1587 (6)	0.0775 (14)
H26	1.1282	0.8982	1.2539	0.093*
C29	1.1170 (3)	0.8691 (3)	0.8720 (6)	0.0690 (12)
C15	0.0576 (3)	0.6322 (3)	0.0508 (5)	0.0633 (11)
C31	1.0376 (3)	0.8483 (3)	0.6437 (5)	0.0758 (13)
H31	1.0366	0.8410	0.5489	0.091*
C13	0.1052 (3)	0.6624 (3)	0.2987 (5)	0.0784 (14)
H13	0.0937	0.6706	0.3893	0.094*
C27	1.1974 (3)	0.8886 (4)	1.0983 (7)	0.0917 (17)
H27	1.2494	0.8944	1.1542	0.110*
C84	0.6968 (4)	0.7930 (5)	0.2133 (7)	0.135 (3)
H84A	0.6787	0.7928	0.1187	0.203*
H84B	0.7138	0.7265	0.2113	0.203*
H84C	0.7435	0.8367	0.2543	0.203*
C30	1.1111 (3)	0.8579 (3)	0.7265 (6)	0.0803 (14)
H30	1.1601	0.8571	0.6876	0.096*
C4	0.0915 (3)	0.6084 (3)	−0.2219 (5)	0.0815 (14)
H4	0.1030	0.6015	−0.3120	0.098*
C86	0.4449 (3)	0.8941 (5)	0.1095 (6)	0.1044 (19)
H86A	0.4075	0.9240	0.1788	0.157*
H86B	0.4578	0.8262	0.1049	0.157*
H86C	0.4185	0.8952	0.0187	0.157*
C28	1.1943 (3)	0.8781 (3)	0.9609 (7)	0.0860 (16)
H28	1.2440	0.8767	0.9236	0.103*
C5	0.0071 (3)	0.6053 (3)	−0.2007 (7)	0.0865 (16)
C16	−0.0092 (3)	0.6178 (3)	−0.0621 (7)	0.0791 (15)
C11	−0.0461 (4)	0.6422 (4)	0.2113 (8)	0.104 (2)
H11	−0.0589	0.6504	0.3012	0.124*
C10	−0.1069 (4)	0.6270 (4)	0.1048 (11)	0.125 (3)
H10	−0.1616	0.6233	0.1220	0.150*
C7	−0.1422 (6)	0.5929 (7)	−0.2790 (12)	0.164 (5)
H7	−0.1869	0.5858	−0.3508	0.196*
C9	−0.0932 (3)	0.6158 (4)	−0.0350 (10)	0.110 (2)
C8	−0.1574 (5)	0.6029 (5)	−0.1473 (12)	0.153 (5)
H8	−0.2126	0.6012	−0.1311	0.183*
C6	−0.0606 (4)	0.5930 (4)	−0.3082 (8)	0.125 (3)
H6	−0.0508	0.5849	−0.3996	0.150*
Au4	0.50364 (3)	0.53222 (3)	0.50258 (5)	0.06749 (14)	0.5
P3	0.4470 (3)	0.5714 (4)	0.7107 (5)	0.0728 (13)	0.5
P4	0.5593 (3)	0.4717 (3)	0.2913 (5)	0.0481 (8)	0.5
C113	0.4745 (16)	0.451 (3)	0.1370 (19)	0.115 (14)	0.5
H11A	0.4673	0.5130	0.1148	0.138*	0.5
H11B	0.4951	0.4008	0.0566	0.138*	0.5
C104	0.584 (3)	0.629 (4)	0.874 (7)	0.104 (15)	0.29 (2)
H10A	0.6041	0.6199	0.7849	0.157*	0.29 (2)
H10B	0.6309	0.6226	0.9412	0.157*	0.29 (2)
H10C	0.5592	0.6950	0.9075	0.157*	0.29 (2)
C103	0.5160 (16)	0.5470 (17)	0.852 (3)	0.052 (6)	0.29 (2)
H10D	0.4886	0.5595	0.9360	0.062*	0.29 (2)
H10E	0.5398	0.4796	0.8242	0.062*	0.29 (2)
C114	0.399 (2)	0.425 (2)	0.147 (4)	0.111 (11)	0.5
H11C	0.3624	0.4179	0.0601	0.167*	0.5
H11D	0.3755	0.4747	0.2235	0.167*	0.5
H11E	0.4032	0.3619	0.1636	0.167*	0.5
C112	0.6893 (16)	0.347 (3)	0.385 (3)	0.116 (10)	0.5
H11F	0.6748	0.3864	0.4760	0.174*	0.5
H11G	0.7358	0.3760	0.3643	0.174*	0.5
H11H	0.7047	0.2802	0.3837	0.174*	0.5
C111	0.6047 (19)	0.343 (2)	0.259 (3)	0.086 (7)	0.5
H11I	0.5627	0.2991	0.2638	0.103*	0.5
H11J	0.6222	0.3175	0.1653	0.103*	0.5
C115	0.6346 (11)	0.5540 (13)	0.2712 (17)	0.063 (3)	0.5
H11K	0.6604	0.5185	0.1868	0.075*	0.5
H11L	0.6037	0.6111	0.2552	0.075*	0.5
C116	0.7034 (11)	0.5922 (17)	0.391 (2)	0.087 (4)	0.5
H11M	0.6793	0.6219	0.4779	0.131*	0.5
H11N	0.7343	0.6414	0.3745	0.131*	0.5
H11O	0.7406	0.5378	0.3985	0.131*	0.5
C102	0.3152 (16)	0.676 (2)	0.640 (3)	0.099 (8)	0.5
H10F	0.2741	0.6268	0.6239	0.148*	0.5
H10G	0.3396	0.6653	0.5548	0.148*	0.5
H10H	0.2888	0.7417	0.6675	0.148*	0.5
C101	0.374 (2)	0.6707 (19)	0.740 (2)	0.085 (9)	0.5
H10I	0.3462	0.6711	0.8192	0.102*	0.5
H10J	0.4053	0.7318	0.7711	0.102*	0.5
C105	0.3912 (15)	0.4686 (15)	0.717 (2)	0.107 (7)	0.5
H10K	0.4315	0.4157	0.7233	0.129*	0.5
H10L	0.3645	0.4905	0.8027	0.129*	0.5
C106	0.3230 (17)	0.425 (2)	0.589 (3)	0.156 (11)	0.5
H10M	0.2755	0.4702	0.5954	0.233*	0.5
H10N	0.3055	0.3617	0.5899	0.233*	0.5
H10O	0.3458	0.4148	0.5029	0.233*	0.5
C203	0.5229 (16)	0.636 (3)	0.868 (3)	0.070 (8)	0.21 (2)
H20A	0.5191	0.7066	0.8818	0.085*	0.21 (2)
H20B	0.5052	0.6265	0.9499	0.085*	0.21 (2)
C204	0.609 (4)	0.604 (5)	0.862 (9)	0.071 (15)	0.21 (2)
H20C	0.6276	0.6129	0.7817	0.107*	0.21 (2)
H20D	0.6144	0.5350	0.8547	0.107*	0.21 (2)
H20E	0.6421	0.6436	0.9469	0.107*	0.21 (2)

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
Au2	0.05237 (12)	0.06738 (15)	0.04691 (11)	0.00370 (10)	0.01713 (9)	0.02373 (10)
Au1	0.04725 (9)	0.07435 (13)	0.06321 (10)	−0.00719 (7)	0.00691 (7)	0.02368 (9)
P1	0.0540 (5)	0.0518 (6)	0.0516 (5)	0.0025 (4)	0.0205 (4)	0.0195 (5)
O2	0.064 (2)	0.146 (3)	0.0618 (19)	−0.004 (2)	0.0168 (15)	0.027 (2)
C85	0.070 (3)	0.090 (3)	0.046 (2)	−0.006 (2)	0.0120 (19)	0.022 (2)
O1	0.061 (2)	0.184 (4)	0.0548 (17)	0.010 (2)	0.0173 (15)	0.021 (2)
C19	0.060 (3)	0.070 (3)	0.065 (3)	0.000 (2)	0.009 (2)	0.026 (2)
C34	0.061 (2)	0.060 (3)	0.046 (2)	−0.0016 (19)	0.0003 (17)	0.0145 (18)
C81	0.066 (3)	0.066 (3)	0.069 (3)	−0.004 (2)	0.020 (2)	0.026 (2)
C22	0.052 (2)	0.037 (2)	0.050 (2)	−0.0036 (15)	0.0022 (16)	0.0125 (16)
C38	0.054 (2)	0.069 (3)	0.075 (3)	−0.005 (2)	0.007 (2)	0.027 (2)
C39	0.053 (2)	0.064 (3)	0.078 (3)	−0.006 (2)	0.010 (2)	0.028 (2)
C18	0.061 (3)	0.076 (3)	0.058 (2)	0.003 (2)	0.012 (2)	0.021 (2)
C1	0.055 (2)	0.040 (2)	0.055 (2)	0.0030 (16)	0.0166 (18)	0.0133 (17)
C23	0.063 (2)	0.049 (2)	0.059 (2)	−0.0021 (18)	0.0056 (19)	0.0195 (19)
C21	0.056 (2)	0.040 (2)	0.052 (2)	0.0003 (16)	0.0058 (17)	0.0128 (17)
C3	0.067 (3)	0.062 (3)	0.064 (3)	−0.007 (2)	0.000 (2)	0.024 (2)
C32	0.061 (2)	0.044 (2)	0.062 (2)	0.0031 (18)	0.0153 (19)	0.0134 (18)
C82	0.082 (3)	0.102 (4)	0.081 (3)	−0.024 (3)	−0.002 (3)	0.022 (3)
C37	0.056 (2)	0.060 (3)	0.064 (2)	−0.0043 (19)	0.0054 (19)	0.023 (2)
C36	0.052 (2)	0.0312 (19)	0.074 (3)	0.0000 (16)	0.0003 (19)	0.0143 (18)
C25	0.059 (2)	0.035 (2)	0.080 (3)	−0.0039 (17)	−0.010 (2)	0.017 (2)
C83	0.089 (4)	0.063 (3)	0.119 (4)	0.013 (3)	0.049 (3)	0.034 (3)
C17	0.060 (2)	0.073 (3)	0.053 (2)	0.009 (2)	0.0133 (19)	0.022 (2)
C24	0.078 (3)	0.047 (2)	0.060 (2)	−0.001 (2)	−0.008 (2)	0.0221 (19)
C14	0.080 (3)	0.052 (3)	0.060 (2)	0.008 (2)	0.024 (2)	0.017 (2)
C35	0.053 (2)	0.0326 (19)	0.059 (2)	0.0002 (15)	0.0066 (17)	0.0106 (16)
C2	0.050 (2)	0.034 (2)	0.067 (2)	−0.0024 (15)	0.0064 (18)	0.0141 (17)
C33	0.078 (3)	0.068 (3)	0.049 (2)	0.004 (2)	0.013 (2)	0.016 (2)
C12	0.067 (3)	0.035 (2)	0.122 (4)	0.007 (2)	0.042 (3)	0.020 (2)
C26	0.080 (3)	0.051 (3)	0.093 (3)	−0.009 (2)	−0.029 (3)	0.027 (2)
C29	0.058 (3)	0.038 (2)	0.104 (4)	−0.0018 (18)	0.010 (2)	0.015 (2)
C15	0.053 (2)	0.031 (2)	0.104 (3)	0.0045 (17)	0.017 (2)	0.019 (2)
C31	0.080 (3)	0.065 (3)	0.080 (3)	0.007 (2)	0.034 (3)	0.013 (2)
C13	0.102 (4)	0.055 (3)	0.087 (3)	0.008 (3)	0.054 (3)	0.019 (2)
C27	0.064 (3)	0.065 (3)	0.136 (5)	−0.011 (2)	−0.021 (3)	0.032 (3)
C84	0.155 (6)	0.097 (5)	0.173 (6)	0.050 (4)	0.098 (5)	0.049 (5)
C30	0.066 (3)	0.064 (3)	0.109 (4)	0.004 (2)	0.034 (3)	0.019 (3)
C4	0.103 (4)	0.061 (3)	0.075 (3)	−0.014 (3)	−0.021 (3)	0.027 (2)
C86	0.088 (4)	0.133 (5)	0.086 (4)	−0.031 (4)	−0.005 (3)	0.030 (4)
C28	0.055 (3)	0.056 (3)	0.141 (5)	−0.002 (2)	0.004 (3)	0.027 (3)
C5	0.084 (4)	0.041 (3)	0.122 (5)	−0.012 (2)	−0.034 (3)	0.027 (3)
C16	0.051 (3)	0.033 (2)	0.144 (5)	−0.0010 (18)	−0.007 (3)	0.025 (3)
C11	0.082 (4)	0.053 (3)	0.181 (6)	0.006 (3)	0.072 (4)	0.024 (4)
C10	0.060 (4)	0.046 (3)	0.264 (10)	0.006 (3)	0.058 (5)	0.031 (5)
C7	0.110 (7)	0.078 (5)	0.259 (12)	−0.018 (4)	−0.094 (8)	0.044 (8)
C9	0.057 (3)	0.039 (3)	0.215 (8)	0.002 (2)	0.008 (4)	0.025 (4)
C8	0.062 (4)	0.054 (4)	0.305 (13)	−0.006 (3)	−0.048 (7)	0.040 (7)
C6	0.114 (5)	0.064 (4)	0.168 (6)	−0.018 (3)	−0.074 (5)	0.036 (4)
Au4	0.05461 (18)	0.1044 (4)	0.04069 (13)	0.0121 (3)	0.01689 (12)	0.0190 (3)
P3	0.0571 (17)	0.122 (4)	0.0394 (14)	0.015 (3)	0.0158 (12)	0.026 (3)
P4	0.0555 (16)	0.0525 (19)	0.0379 (12)	0.0071 (16)	0.0148 (10)	0.0153 (15)
C113	0.104 (17)	0.20 (4)	0.025 (6)	−0.001 (15)	−0.012 (7)	0.028 (10)
C104	0.08 (3)	0.15 (4)	0.072 (16)	−0.03 (2)	0.02 (2)	0.02 (3)
C103	0.047 (10)	0.042 (10)	0.071 (16)	0.009 (8)	0.025 (10)	0.019 (9)
C114	0.085 (15)	0.10 (2)	0.121 (15)	−0.016 (13)	−0.037 (11)	0.019 (13)
C112	0.137 (17)	0.111 (19)	0.108 (14)	0.032 (13)	−0.014 (11)	0.066 (13)
C111	0.077 (12)	0.119 (14)	0.099 (13)	0.012 (9)	0.036 (8)	0.075 (12)
C115	0.079 (8)	0.057 (8)	0.059 (7)	0.000 (5)	0.026 (6)	0.022 (5)
C116	0.095 (10)	0.081 (12)	0.078 (8)	−0.017 (8)	0.009 (8)	0.014 (7)
C102	0.107 (14)	0.089 (12)	0.132 (17)	0.007 (9)	0.073 (13)	0.057 (12)
C101	0.092 (18)	0.096 (13)	0.056 (9)	−0.026 (13)	0.031 (9)	−0.001 (9)
C105	0.17 (2)	0.081 (13)	0.099 (11)	0.039 (12)	0.079 (13)	0.046 (9)
C106	0.19 (2)	0.082 (13)	0.19 (2)	−0.045 (13)	0.092 (17)	−0.007 (13)
C203	0.044 (12)	0.088 (19)	0.069 (13)	−0.002 (12)	0.011 (10)	0.012 (12)
C204	0.06 (2)	0.08 (4)	0.07 (3)	−0.02 (2)	0.02 (2)	0.01 (2)

Geometric parameters (Å, º)

Au2—Au1^i	3.3373 (2)	C30—H30	0.9300
Au2—Au1	3.3373 (2)	C4—H4	0.9300
Au2—P1	2.3086 (9)	C4—C5	1.411 (7)
Au2—P1^i	2.3086 (8)	C86—H86A	0.9600
Au1—C19	1.976 (4)	C86—H86B	0.9600
Au1—C39	1.987 (4)	C86—H86C	0.9600
Au1—Au4	3.3289 (4)	C28—H28	0.9300
P1—C85	1.815 (4)	C5—C16	1.416 (8)
P1—C81	1.804 (4)	C5—C6	1.398 (7)
P1—C83	1.817 (5)	C16—C9	1.423 (7)
O2—C37	1.220 (5)	C11—H11	0.9300
C85—H85A	0.9700	C11—C10	1.316 (9)
C85—H85B	0.9700	C10—H10	0.9300
C85—C86	1.509 (6)	C10—C9	1.420 (10)
O1—C17	1.215 (4)	C7—H7	0.9300
C19—C18	1.205 (5)	C7—C8	1.351 (13)
C34—H34	0.9300	C7—C6	1.388 (11)
C34—C21	1.392 (5)	C9—C8	1.392 (10)
C34—C33	1.380 (5)	C8—H8	0.9300
C81—H81A	0.9700	C6—H6	0.9300
C81—H81B	0.9700	Au4—P3	2.299 (5)
C81—C82	1.522 (6)	Au4—P4	2.308 (5)
C22—C23	1.437 (5)	P3—C103	1.80 (3)
C22—C21	1.414 (5)	P3—C101	1.74 (3)
C22—C35	1.426 (5)	P3—C105	1.794 (16)
C38—C39	1.201 (5)	P3—C203	1.86 (3)
C38—C37	1.443 (6)	P4—C113	1.88 (2)
C18—C17	1.436 (6)	P4—C111	1.86 (3)
C1—C17	1.490 (5)	P4—C115	1.821 (13)
C1—C14	1.400 (5)	C113—H11A	0.9700
C1—C2	1.412 (5)	C113—H11B	0.9700
C23—H23	0.9300	C113—C114	1.33 (4)
C23—C24	1.348 (5)	C104—H10A	0.9600
C21—C37	1.498 (5)	C104—H10B	0.9600
C3—H3	0.9300	C104—H10C	0.9600
C3—C2	1.441 (5)	C104—C103	1.60 (6)
C3—C4	1.343 (6)	C103—H10D	0.9700
C32—C35	1.417 (5)	C103—H10E	0.9700
C32—C33	1.392 (6)	C114—H11C	0.9600
C32—C31	1.438 (5)	C114—H11D	0.9600
C82—H82A	0.9600	C114—H11E	0.9600
C82—H82B	0.9600	C112—H11F	0.9600
C82—H82C	0.9600	C112—H11G	0.9600
C36—C25	1.400 (6)	C112—H11H	0.9600
C36—C35	1.434 (5)	C112—C111	1.71 (4)
C36—C29	1.422 (6)	C111—H11I	0.9700
C25—C24	1.422 (6)	C111—H11J	0.9700
C25—C26	1.410 (6)	C115—H11K	0.9700
C83—H83A	0.9700	C115—H11L	0.9700
C83—H83B	0.9700	C115—C116	1.50 (3)
C83—C84	1.466 (6)	C116—H11M	0.9600
C24—H24	0.9300	C116—H11N	0.9600
C14—H14	0.9300	C116—H11O	0.9600
C14—C13	1.379 (6)	C102—H10F	0.9600
C2—C15	1.429 (5)	C102—H10G	0.9600
C33—H33	0.9300	C102—H10H	0.9600
C12—C15	1.422 (7)	C102—C101	1.30 (4)
C12—C13	1.371 (7)	C101—H10I	0.9700
C12—C11	1.449 (6)	C101—H10J	0.9700
C26—H26	0.9300	C105—H10K	0.9700
C26—C27	1.389 (7)	C105—H10L	0.9700
C29—C30	1.419 (7)	C105—C106	1.55 (4)
C29—C28	1.411 (6)	C106—H10M	0.9600
C15—C16	1.421 (7)	C106—H10N	0.9600
C31—H31	0.9300	C106—H10O	0.9600
C31—C30	1.332 (6)	C203—H20A	0.9700
C13—H13	0.9300	C203—H20B	0.9700
C27—H27	0.9300	C203—C204	1.42 (6)
C27—C28	1.343 (7)	C204—H20C	0.9600
C84—H84A	0.9600	C204—H20D	0.9600
C84—H84B	0.9600	C204—H20E	0.9600
C84—H84C	0.9600
Au1^i—Au2—Au1	180.0	H86B—C86—H86C	109.5
P1—Au2—Au1^i	86.43 (3)	C29—C28—H28	119.3
P1^i—Au2—Au1	86.42 (3)	C27—C28—C29	121.3 (5)
P1^i—Au2—Au1^i	93.58 (3)	C27—C28—H28	119.3
P1—Au2—Au1	93.57 (3)	C4—C5—C16	117.6 (5)
P1—Au2—P1^i	180.0	C6—C5—C4	123.4 (7)
C19—Au1—Au2	94.50 (13)	C6—C5—C16	119.0 (6)
C19—Au1—C39	177.23 (17)	C15—C16—C9	119.4 (6)
C19—Au1—Au4	83.46 (13)	C5—C16—C15	120.8 (4)
C39—Au1—Au2	86.64 (12)	C5—C16—C9	119.8 (6)
C39—Au1—Au4	95.17 (12)	C12—C11—H11	119.7
Au4—Au1—Au2	174.547 (9)	C10—C11—C12	120.7 (6)
C85—P1—Au2	113.35 (14)	C10—C11—H11	119.7
C85—P1—C83	108.8 (2)	C11—C10—H10	118.3
C81—P1—Au2	113.61 (14)	C11—C10—C9	123.4 (6)
C81—P1—C85	104.4 (2)	C9—C10—H10	118.3
C81—P1—C83	106.6 (2)	C8—C7—H7	119.7
C83—P1—Au2	109.69 (16)	C8—C7—C6	120.6 (9)
P1—C85—H85A	108.9	C6—C7—H7	119.7
P1—C85—H85B	108.9	C10—C9—C16	118.2 (6)
H85A—C85—H85B	107.7	C8—C9—C16	118.0 (8)
C86—C85—P1	113.6 (3)	C8—C9—C10	123.8 (8)
C86—C85—H85A	108.9	C7—C8—C9	122.3 (10)
C86—C85—H85B	108.9	C7—C8—H8	118.9
C18—C19—Au1	178.0 (4)	C9—C8—H8	118.9
C21—C34—H34	119.0	C5—C6—H6	119.9
C33—C34—H34	119.0	C7—C6—C5	120.3 (8)
C33—C34—C21	122.0 (4)	C7—C6—H6	119.9
P1—C81—H81A	108.7	P3—Au4—Au1	92.80 (12)
P1—C81—H81B	108.7	P3—Au4—P4	172.62 (13)
H81A—C81—H81B	107.6	P4—Au4—Au1	94.54 (8)
C82—C81—P1	114.4 (3)	C103—P3—Au4	114.6 (7)
C82—C81—H81A	108.7	C103—P3—C203	39.1 (17)
C82—C81—H81B	108.7	C101—P3—Au4	114.8 (8)
C21—C22—C23	124.5 (3)	C101—P3—C103	122.3 (11)
C21—C22—C35	118.5 (3)	C101—P3—C105	104.6 (12)
C35—C22—C23	117.0 (3)	C101—P3—C203	94.5 (13)
C39—C38—C37	179.4 (5)	C105—P3—Au4	111.6 (7)
C38—C39—Au1	175.5 (4)	C105—P3—C103	82.8 (11)
C19—C18—C17	175.0 (4)	C105—P3—C203	117.7 (15)
C14—C1—C17	116.5 (4)	C203—P3—Au4	112.3 (9)
C14—C1—C2	119.7 (4)	C113—P4—Au4	111.1 (7)
C2—C1—C17	123.9 (3)	C111—P4—Au4	112.2 (8)
C22—C23—H23	118.9	C111—P4—C113	101.4 (16)
C24—C23—C22	122.2 (4)	C115—P4—Au4	114.0 (6)
C24—C23—H23	118.9	C115—P4—C113	106.5 (13)
C34—C21—C22	119.4 (3)	C115—P4—C111	110.8 (11)
C34—C21—C37	117.3 (3)	P4—C113—H11A	107.4
C22—C21—C37	123.3 (3)	P4—C113—H11B	107.4
C2—C3—H3	119.1	H11A—C113—H11B	107.0
C4—C3—H3	119.1	C114—C113—P4	120 (2)
C4—C3—C2	121.7 (4)	C114—C113—H11A	107.4
C35—C32—C31	118.9 (4)	C114—C113—H11B	107.4
C33—C32—C35	118.9 (4)	H10A—C104—H10B	109.5
C33—C32—C31	122.2 (4)	H10A—C104—H10C	109.5
C81—C82—H82A	109.5	H10B—C104—H10C	109.5
C81—C82—H82B	109.5	C103—C104—H10A	109.5
C81—C82—H82C	109.5	C103—C104—H10B	109.5
H82A—C82—H82B	109.5	C103—C104—H10C	109.5
H82A—C82—H82C	109.5	P3—C103—H10D	112.2
H82B—C82—H82C	109.5	P3—C103—H10E	112.2
O2—C37—C38	119.7 (4)	C104—C103—P3	98 (3)
O2—C37—C21	123.3 (4)	C104—C103—H10D	112.2
C38—C37—C21	116.9 (4)	C104—C103—H10E	112.2
C25—C36—C35	120.6 (4)	H10D—C103—H10E	109.8
C25—C36—C29	119.5 (4)	C113—C114—H11C	109.5
C29—C36—C35	119.9 (4)	C113—C114—H11D	109.5
C36—C25—C24	118.3 (4)	C113—C114—H11E	109.5
C36—C25—C26	119.8 (4)	H11C—C114—H11D	109.5
C26—C25—C24	121.9 (4)	H11C—C114—H11E	109.5
P1—C83—H83A	107.6	H11D—C114—H11E	109.5
P1—C83—H83B	107.6	H11F—C112—H11G	109.5
H83A—C83—H83B	107.1	H11F—C112—H11H	109.5
C84—C83—P1	118.8 (4)	H11G—C112—H11H	109.5
C84—C83—H83A	107.6	C111—C112—H11F	109.5
C84—C83—H83B	107.6	C111—C112—H11G	109.5
O1—C17—C18	119.3 (4)	C111—C112—H11H	109.5
O1—C17—C1	122.3 (4)	P4—C111—H11I	109.9
C18—C17—C1	118.4 (3)	P4—C111—H11J	109.9
C23—C24—C25	121.8 (4)	C112—C111—P4	108.8 (18)
C23—C24—H24	119.1	C112—C111—H11I	109.9
C25—C24—H24	119.1	C112—C111—H11J	109.9
C1—C14—H14	119.5	H11I—C111—H11J	108.3
C13—C14—C1	121.0 (4)	P4—C115—H11K	108.0
C13—C14—H14	119.5	P4—C115—H11L	108.0
C22—C35—C36	120.1 (3)	H11K—C115—H11L	107.3
C32—C35—C22	120.7 (3)	C116—C115—P4	117.0 (10)
C32—C35—C36	119.2 (3)	C116—C115—H11K	108.0
C1—C2—C3	124.2 (3)	C116—C115—H11L	108.0
C1—C2—C15	118.8 (4)	C115—C116—H11M	109.5
C15—C2—C3	117.0 (4)	C115—C116—H11N	109.5
C34—C33—C32	120.5 (4)	C115—C116—H11O	109.5
C34—C33—H33	119.8	H11M—C116—H11N	109.5
C32—C33—H33	119.8	H11M—C116—H11O	109.5
C15—C12—C11	118.0 (6)	H11N—C116—H11O	109.5
C13—C12—C15	119.9 (4)	H10F—C102—H10G	109.5
C13—C12—C11	122.1 (5)	H10F—C102—H10H	109.5
C25—C26—H26	120.2	H10G—C102—H10H	109.5
C27—C26—C25	119.5 (5)	C101—C102—H10F	109.5
C27—C26—H26	120.2	C101—C102—H10G	109.5
C30—C29—C36	118.5 (4)	C101—C102—H10H	109.5
C28—C29—C36	118.5 (5)	P3—C101—H10I	107.1
C28—C29—C30	123.0 (5)	P3—C101—H10J	107.1
C12—C15—C2	119.5 (4)	C102—C101—P3	121 (2)
C16—C15—C2	120.1 (5)	C102—C101—H10I	107.1
C16—C15—C12	120.4 (4)	C102—C101—H10J	107.1
C32—C31—H31	119.4	H10I—C101—H10J	106.8
C30—C31—C32	121.3 (4)	P3—C105—H10K	108.5
C30—C31—H31	119.4	P3—C105—H10L	108.5
C14—C13—H13	119.4	H10K—C105—H10L	107.5
C12—C13—C14	121.1 (4)	C106—C105—P3	115.1 (15)
C12—C13—H13	119.4	C106—C105—H10K	108.5
C26—C27—H27	119.3	C106—C105—H10L	108.5
C28—C27—C26	121.4 (5)	C105—C106—H10M	109.5
C28—C27—H27	119.3	C105—C106—H10N	109.5
C83—C84—H84A	109.5	C105—C106—H10O	109.5
C83—C84—H84B	109.5	H10M—C106—H10N	109.5
C83—C84—H84C	109.5	H10M—C106—H10O	109.5
H84A—C84—H84B	109.5	H10N—C106—H10O	109.5
H84A—C84—H84C	109.5	P3—C203—H20A	108.1
H84B—C84—H84C	109.5	P3—C203—H20B	108.1
C29—C30—H30	118.9	H20A—C203—H20B	107.3
C31—C30—C29	122.2 (4)	C204—C203—P3	117 (4)
C31—C30—H30	118.9	C204—C203—H20A	108.1
C3—C4—H4	118.7	C204—C203—H20B	108.1
C3—C4—C5	122.7 (5)	C203—C204—H20C	109.5
C5—C4—H4	118.7	C203—C204—H20D	109.5
C85—C86—H86A	109.5	C203—C204—H20E	109.5
C85—C86—H86B	109.5	H20C—C204—H20D	109.5
C85—C86—H86C	109.5	H20C—C204—H20E	109.5
H86A—C86—H86B	109.5	H20D—C204—H20E	109.5
H86A—C86—H86C	109.5
Au2—P1—C85—C86	−51.4 (4)	C33—C32—C31—C30	−179.5 (4)
Au2—P1—C81—C82	55.0 (4)	C12—C15—C16—C5	178.9 (4)
Au2—P1—C83—C84	−165.7 (5)	C12—C15—C16—C9	−1.2 (6)
C85—P1—C81—C82	179.0 (3)	C12—C11—C10—C9	−1.3 (9)
C85—P1—C83—C84	69.8 (6)	C26—C25—C24—C23	179.4 (4)
C34—C21—C37—O2	−162.1 (4)	C26—C27—C28—C29	0.0 (8)
C34—C21—C37—C38	14.8 (5)	C29—C36—C25—C24	−179.5 (4)
C81—P1—C85—C86	−175.6 (4)	C29—C36—C25—C26	−1.0 (6)
C81—P1—C83—C84	−42.2 (6)	C29—C36—C35—C22	−178.7 (3)
C22—C23—C24—C25	1.3 (6)	C29—C36—C35—C32	1.1 (5)
C22—C21—C37—O2	15.2 (6)	C15—C12—C13—C14	1.0 (6)
C22—C21—C37—C38	−167.8 (4)	C15—C12—C11—C10	−0.8 (7)
C1—C14—C13—C12	−2.5 (6)	C15—C16—C9—C10	−0.9 (7)
C1—C2—C15—C12	−0.9 (5)	C15—C16—C9—C8	179.1 (5)
C1—C2—C15—C16	178.3 (3)	C31—C32—C35—C22	178.2 (4)
C23—C22—C21—C34	−176.5 (4)	C31—C32—C35—C36	−1.6 (5)
C23—C22—C21—C37	6.2 (6)	C31—C32—C33—C34	−179.1 (4)
C23—C22—C35—C32	178.7 (3)	C13—C12—C15—C2	0.7 (6)
C23—C22—C35—C36	−1.5 (5)	C13—C12—C15—C16	−178.6 (4)
C21—C34—C33—C32	1.8 (6)	C13—C12—C11—C10	179.8 (5)
C21—C22—C23—C24	179.1 (4)	C30—C29—C28—C27	−180.0 (5)
C21—C22—C35—C32	0.0 (5)	C4—C3—C2—C1	−177.5 (4)
C21—C22—C35—C36	179.8 (3)	C4—C3—C2—C15	0.4 (6)
C3—C2—C15—C12	−178.9 (4)	C4—C5—C16—C15	−0.4 (6)
C3—C2—C15—C16	0.3 (5)	C4—C5—C16—C9	179.7 (4)
C3—C4—C5—C16	1.1 (7)	C4—C5—C6—C7	−178.6 (6)
C3—C4—C5—C6	179.6 (5)	C28—C29—C30—C31	179.2 (4)
C32—C31—C30—C29	0.0 (7)	C5—C16—C9—C10	179.0 (5)
C36—C25—C24—C23	−2.1 (6)	C5—C16—C9—C8	−1.0 (7)
C36—C25—C26—C27	0.7 (6)	C16—C5—C6—C7	−0.2 (8)
C36—C29—C30—C31	−0.5 (7)	C16—C9—C8—C7	−0.3 (11)
C36—C29—C28—C27	−0.3 (7)	C11—C12—C15—C2	−178.7 (4)
C25—C36—C35—C22	0.7 (5)	C11—C12—C15—C16	2.1 (6)
C25—C36—C35—C32	−179.5 (3)	C11—C12—C13—C14	−179.6 (4)
C25—C36—C29—C30	−179.5 (4)	C11—C10—C9—C16	2.2 (8)
C25—C36—C29—C28	0.8 (6)	C11—C10—C9—C8	−177.8 (6)
C25—C26—C27—C28	−0.2 (7)	C10—C9—C8—C7	179.7 (8)
C83—P1—C85—C86	70.9 (4)	C8—C7—C6—C5	−1.1 (12)
C83—P1—C81—C82	−65.9 (4)	C6—C5—C16—C15	−178.9 (4)
C17—C1—C14—C13	−177.9 (4)	C6—C5—C16—C9	1.2 (7)
C17—C1—C2—C3	−2.5 (6)	C6—C7—C8—C9	1.3 (15)
C17—C1—C2—C15	179.7 (4)	Au4—P3—C103—C104	67 (2)
C24—C25—C26—C27	179.2 (4)	Au4—P3—C101—C102	45 (3)
C14—C1—C17—O1	164.9 (4)	Au4—P3—C105—C106	−53.4 (19)
C14—C1—C17—C18	−14.1 (6)	Au4—P3—C203—C204	−36 (5)
C14—C1—C2—C3	177.4 (4)	Au4—P4—C113—C114	−32 (4)
C14—C1—C2—C15	−0.5 (5)	Au4—P4—C111—C112	−65.3 (16)
C35—C22—C23—C24	0.5 (5)	Au4—P4—C115—C116	49.7 (17)
C35—C22—C21—C34	2.1 (5)	C113—P4—C111—C112	176.1 (16)
C35—C22—C21—C37	−175.2 (3)	C113—P4—C115—C116	172.5 (17)
C35—C32—C33—C34	0.4 (6)	C103—P3—C101—C102	−167.9 (19)
C35—C32—C31—C30	1.0 (6)	C103—P3—C105—C106	−167.1 (19)
C35—C36—C25—C24	1.0 (5)	C103—P3—C203—C204	66 (4)
C35—C36—C25—C26	179.6 (4)	C111—P4—C113—C114	87 (3)
C35—C36—C29—C30	−0.1 (6)	C111—P4—C115—C116	−78.0 (18)
C35—C36—C29—C28	−179.8 (4)	C115—P4—C113—C114	−157 (3)
C2—C1—C17—O1	−15.3 (7)	C115—P4—C111—C112	63.3 (16)
C2—C1—C17—C18	165.7 (4)	C101—P3—C103—C104	−80 (2)
C2—C1—C14—C13	2.2 (6)	C101—P3—C105—C106	71.3 (19)
C2—C3—C4—C5	−1.2 (7)	C101—P3—C203—C204	−155 (4)
C2—C15—C16—C5	−0.3 (6)	C105—P3—C103—C104	177 (2)
C2—C15—C16—C9	179.6 (4)	C105—P3—C101—C102	−77 (2)
C33—C34—C21—C22	−3.1 (6)	C105—P3—C203—C204	96 (4)
C33—C34—C21—C37	174.4 (4)	C203—P3—C103—C104	−29 (2)
C33—C32—C35—C22	−1.3 (6)	C203—P3—C101—C102	163 (2)
C33—C32—C35—C36	178.9 (4)	C203—P3—C105—C106	174.6 (18)

Symmetry code: (i) −x+1, −y+2, −z+1.

(crystal_4a)

Crystal data

C25H24AuOP	Z = 4
Mr = 568.38	F(000) = 1104
Triclinic, P1	Dx = 1.905 Mg m^−3
a = 15.906 (7) Å	Synchrotron radiation, λ = 0.41004 Å
b = 13.677 (2) Å	Cell parameters from 4078 reflections
c = 9.7733 (14) Å	θ = 2.4–21.4°
α = 109.591 (15)°	µ = 1.84 mm^−1
β = 98.20 (2)°	T = 293 K
γ = 86.14 (3)°	Prism, yellow
V = 1982.2 (10) Å^3	0.06 × 0.05 × 0.02 mm

Data collection

Esperanto-CrysAlisPro-abstract goniometer imported esperanto images diffractometer	3120 independent reflections
Radiation source: synchrotron	886 reflections with I > 2σ(I)
Synchrotron monochromator	Rint = 0.046
Detector resolution: 13.3333 pixels mm^-1	θmax = 21.4°, θmin = 2.4°
ω scans	h = −8→8
Absorption correction: multi-scan CrysAlisPro 1.171.42.49 (Rigaku Oxford Diffraction, 2022) Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm.	k = −21→22
Tmin = 0.362, Tmax = 1.000	l = −13→13
4078 measured reflections

Refinement

Refinement on F^2	279 restraints
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F^2 > 2σ(F^2)] = 0.123	H-atom parameters constrained
wR(F^2) = 0.368	w = 1/[σ^2(Fo^2) + (0.1727P)^2] where P = (Fo^2 + 2Fc^2)/3
S = 0.91	(Δ/σ)max = 0.001
3120 reflections	Δρmax = 1.09 e Å^−3
263 parameters	Δρmin = −0.77 e Å^−3

Special details

Experimental. High-pressure measurement at 0.8 GPa in a Membrane Diamond Anvil Cell with effective opening angle of 35 deg. and helium used as a pressure medium. Pressure determined by monitoring the shift of the ruby R1-fluorescence line.

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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Ų)

	x	y	z	Uiso*/Ueq	Occ. (<1)
Au2	0.500000	1.000000	0.500000	0.130 (5)
Au1	0.4960 (3)	0.76867 (14)	0.51458 (18)	0.139 (5)
P1	0.5789 (18)	0.9543 (8)	0.3125 (10)	0.114 (18)
O2	0.725 (5)	0.904 (2)	0.992 (3)	0.138 (11)*
C85	0.501 (6)	0.951 (4)	0.154 (4)	0.22 (4)
H85A	0.482058	1.022854	0.168534	0.261*
H85B	0.531794	0.930742	0.069813	0.261*
O1	0.331 (5)	0.602 (3)	0.016 (4)	0.172 (14)*
C19	0.401 (4)	0.728 (2)	0.369 (3)	0.074 (9)*
C34	0.819 (3)	0.8446 (16)	0.660 (2)	0.087 (10)*
H34	0.768825	0.839465	0.597377	0.104*
C21	0.817 (3)	0.8587 (17)	0.807 (2)	0.081 (10)*
C22	0.893 (3)	0.8664 (11)	0.9012 (16)	0.062 (8)*
C35	0.970 (3)	0.8598 (14)	0.848 (2)	0.069 (9)*
C32	0.972 (3)	0.8457 (18)	0.701 (2)	0.105 (13)*
C33	0.897 (3)	0.8380 (15)	0.6069 (17)	0.074 (9)*
H33	0.898013	0.828571	0.508401	0.089*
C81	0.653 (6)	1.038 (3)	0.346 (4)	0.13 (3)
H81A	0.688317	1.014291	0.267794	0.159*
H81B	0.626062	1.103245	0.342362	0.159*
C38	0.665 (5)	0.833 (3)	0.752 (4)	0.103 (14)*
C39	0.601 (4)	0.814 (3)	0.672 (4)	0.109 (15)*
C18	0.338 (4)	0.692 (3)	0.274 (4)	0.146 (19)*
C1	0.200 (3)	0.6459 (18)	0.133 (3)	0.087 (11)*
C2	0.137 (3)	0.6308 (14)	0.0148 (18)	0.115 (16)*
C15	0.052 (3)	0.6285 (18)	0.035 (3)	0.097 (12)*
C12	0.031 (3)	0.6415 (19)	0.173 (4)	0.18 (2)*
C13	0.094 (3)	0.6567 (16)	0.291 (2)	0.099 (12)*
H13	0.080223	0.665341	0.383759	0.119*
C14	0.179 (3)	0.6589 (19)	0.271 (2)	0.103 (13)*
H14	0.221400	0.669028	0.350717	0.124*
C23	0.898 (4)	0.8798 (17)	1.052 (2)	0.088 (11)*
H23	0.847749	0.886689	1.093731	0.105*
C3	0.158 (3)	0.6180 (19)	−0.126 (3)	0.089 (11)*
H3	0.214387	0.615871	−0.143341	0.106*
C82	0.706 (7)	1.058 (5)	0.481 (4)	0.17 (3)
H82A	0.747196	1.108862	0.488586	0.249*
H82B	0.672451	1.084522	0.560016	0.249*
H82C	0.734918	0.995267	0.485194	0.249*
C37	0.737 (4)	0.873 (3)	0.863 (3)	0.084 (10)*
C36	1.049 (3)	0.868 (2)	0.936 (3)	0.107 (14)*
C25	1.052 (3)	0.8802 (19)	1.083 (3)	0.078 (10)*
C26	1.130 (3)	0.8895 (19)	1.171 (2)	0.100 (12)*
H26	1.131902	0.897499	1.270069	0.120*
C27	1.205 (3)	0.887 (3)	1.112 (3)	0.124 (16)*
H27	1.256657	0.892919	1.170478	0.149*
C28	1.201 (3)	0.875 (3)	0.964 (4)	0.15 (2)*
H28	1.251486	0.872886	0.924137	0.175*
C29	1.124 (3)	0.865 (2)	0.876 (2)	0.105 (13)*
C83	0.645 (6)	0.827 (3)	0.298 (4)	0.088 (19)
H83A	0.665850	0.830333	0.397694	0.106*
H83B	0.604315	0.770888	0.260831	0.106*
C17	0.295 (3)	0.640 (3)	0.129 (4)	0.14 (2)*
C24	0.976 (3)	0.883 (2)	1.140 (4)	0.074 (9)*
H24	0.976593	0.887270	1.237385	0.089*
C31	1.045 (4)	0.849 (2)	0.638 (4)	0.086 (10)*
H31	1.041711	0.849354	0.542379	0.103*
C84	0.717 (7)	0.792 (4)	0.214 (5)	0.16 (3)
H84A	0.738881	0.727407	0.223077	0.234*
H84B	0.697949	0.783320	0.112724	0.234*
H84C	0.760056	0.843319	0.250861	0.234*
C30	1.122 (4)	0.852 (3)	0.726 (3)	0.139 (19)*
H30	1.172841	0.844461	0.685816	0.167*
C4	0.091 (3)	0.609 (3)	−0.236 (4)	0.102 (14)*
H4	0.103692	0.611092	−0.324947	0.122*
C86	0.422 (7)	0.888 (4)	0.108 (4)	0.19 (4)
H86A	0.390764	0.899168	0.022098	0.282*
H86B	0.437044	0.815973	0.085904	0.282*
H86C	0.386844	0.908945	0.185546	0.282*
C5	0.005 (3)	0.597 (2)	−0.228 (4)	0.103 (14)*
C6	−0.062 (4)	0.585 (2)	−0.339 (3)	0.122 (16)*
H6	−0.051973	0.575290	−0.434102	0.147*
C7	−0.145 (3)	0.587 (3)	−0.308 (5)	0.22 (4)*
H7	−0.190311	0.579154	−0.382474	0.263*
C8	−0.160 (3)	0.602 (4)	−0.166 (6)	0.22 (4)*
H8	−0.215881	0.603229	−0.145381	0.267*
C9	−0.093 (4)	0.614 (3)	−0.055 (4)	0.130 (18)*
C16	−0.010 (3)	0.611 (2)	−0.086 (3)	0.16 (2)*
C11	−0.054 (3)	0.642 (3)	0.193 (4)	0.107 (13)*
H11	−0.066912	0.652615	0.286949	0.129*
C10	−0.121 (4)	0.627 (3)	0.080 (3)	0.120 (15)*
H10	−0.177436	0.626931	0.091992	0.144*
Au4	0.5081 (12)	0.5291 (4)	0.5009 (8)	0.141 (7)	0.5
P4	0.552 (2)	0.4507 (13)	0.2826 (11)	0.155 (18)
C113	0.450 (6)	0.436 (5)	0.142 (5)	0.16 (3)
H11A	0.425396	0.505224	0.161798	0.188*
H11B	0.470651	0.418493	0.047252	0.188*
C114	0.382 (8)	0.370 (6)	0.120 (6)	0.17 (3)
H11C	0.340709	0.378413	0.043106	0.259*
H11D	0.402760	0.299159	0.092828	0.259*
H11E	0.356993	0.386870	0.208668	0.259*
C112	0.692 (7)	0.340 (4)	0.384 (4)	0.11 (2)
H11F	0.722456	0.274216	0.364814	0.170*
H11G	0.729942	0.392411	0.387059	0.170*
H11H	0.671212	0.357363	0.477234	0.170*
C111	0.612 (7)	0.331 (4)	0.254 (4)	0.11 (2)
H11I	0.574534	0.276659	0.250551	0.136*
H11J	0.633280	0.311717	0.160351	0.136*
C115	0.619 (6)	0.549 (4)	0.271 (5)	0.14 (2)
H11K	0.643575	0.521091	0.180200	0.173*
H11L	0.582310	0.607670	0.263450	0.173*
C116	0.692 (7)	0.591 (3)	0.399 (4)	0.12 (2)
H11M	0.722675	0.642779	0.379728	0.186*
H11N	0.668699	0.622188	0.489192	0.186*
H11O	0.730202	0.535271	0.405618	0.186*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
Au2	0.223 (15)	0.0946 (15)	0.0802 (12)	0.008 (3)	0.066 (3)	0.0218 (9)
Au1	0.196 (16)	0.1063 (16)	0.1189 (14)	0.003 (3)	0.052 (3)	0.0316 (9)
P1	0.17 (6)	0.096 (7)	0.084 (5)	0.001 (13)	0.072 (14)	0.018 (5)
C85	0.36 (10)	0.11 (4)	0.11 (3)	−0.07 (7)	−0.12 (5)	−0.02 (2)
C81	0.20 (8)	0.08 (3)	0.111 (19)	0.03 (5)	0.00 (4)	0.043 (19)
C82	0.11 (8)	0.28 (6)	0.090 (17)	−0.03 (6)	0.04 (3)	0.03 (3)
C83	0.08 (5)	0.07 (2)	0.10 (2)	−0.01 (3)	0.01 (3)	0.013 (15)
C84	0.14 (7)	0.15 (4)	0.19 (4)	0.04 (5)	0.08 (5)	0.06 (3)
C86	0.28 (11)	0.14 (4)	0.09 (2)	−0.02 (6)	0.00 (4)	−0.03 (2)
Au4	0.20 (2)	0.145 (6)	0.0738 (14)	0.026 (10)	0.059 (4)	0.025 (4)
P4	0.18 (5)	0.197 (15)	0.069 (6)	−0.01 (2)	0.050 (13)	0.009 (7)
C113	0.15 (5)	0.17 (4)	0.12 (2)	−0.02 (4)	0.05 (4)	0.00 (2)
C114	0.16 (6)	0.21 (5)	0.16 (3)	−0.03 (5)	0.02 (4)	0.07 (3)
C112	0.09 (6)	0.11 (3)	0.14 (2)	−0.03 (4)	0.04 (3)	0.02 (2)
C111	0.09 (5)	0.14 (3)	0.114 (19)	−0.04 (4)	0.05 (3)	0.03 (2)
C115	0.13 (5)	0.14 (3)	0.13 (2)	0.05 (4)	0.04 (3)	−0.01 (2)
C116	0.12 (6)	0.08 (2)	0.15 (2)	0.06 (4)	0.03 (3)	0.017 (19)

Geometric parameters (Å, º)

Au2—Au1	3.2197 (19)	C26—H26	0.9300
Au2—Au1^i	3.2197 (19)	C26—C27	1.3900
Au2—P1^i	2.260 (15)	C27—H27	0.9300
Au2—P1	2.260 (15)	C27—C28	1.3900
Au1—C19	1.89 (5)	C28—H28	0.9300
Au1—C39	2.08 (6)	C28—C29	1.3900
Au1—Au4	3.228 (5)	C29—C30	1.414 (15)
P1—C85	1.83 (7)	C83—H83A	0.9700
P1—C81	1.62 (7)	C83—H83B	0.9700
P1—C83	1.95 (6)	C83—C84	1.46 (8)
O2—C37	1.23 (3)	C24—H24	0.9300
C85—H85A	0.9700	C31—H31	0.9300
C85—H85B	0.9700	C31—C30	1.392 (16)
C85—C86	1.50 (9)	C84—H84A	0.9600
O1—C17	1.26 (3)	C84—H84B	0.9600
C19—C18	1.28 (6)	C84—H84C	0.9600
C34—H34	0.9300	C30—H30	0.9300
C34—C21	1.3900	C4—H4	0.9300
C34—C33	1.3900	C4—C5	1.394 (16)
C21—C22	1.3900	C86—H86A	0.9600
C21—C37	1.44 (4)	C86—H86B	0.9600
C22—C35	1.3900	C86—H86C	0.9600
C22—C23	1.414 (14)	C5—C6	1.3900
C35—C32	1.3900	C5—C16	1.3900
C35—C36	1.400 (16)	C6—H6	0.9300
C32—C33	1.3900	C6—C7	1.3900
C32—C31	1.392 (16)	C7—H7	0.9300
C33—H33	0.9300	C7—C8	1.3900
C81—H81A	0.9700	C8—H8	0.9300
C81—H81B	0.9700	C8—C9	1.3900
C81—C82	1.41 (7)	C9—C16	1.3900
C38—C39	1.18 (7)	C9—C10	1.395 (16)
C38—C37	1.45 (6)	C11—H11	0.9300
C18—C17	1.44 (4)	C11—C10	1.392 (16)
C1—C2	1.3900	C10—H10	0.9300
C1—C14	1.3900	Au4—P4	2.230 (14)
C1—C17	1.50 (4)	P4—C113	1.94 (8)
C2—C15	1.3900	P4—C111	1.80 (7)
C2—C3	1.413 (15)	P4—C115	1.81 (7)
C15—C12	1.3900	C113—H11A	0.9700
C15—C16	1.392 (16)	C113—H11B	0.9700
C12—C13	1.3900	C113—C114	1.41 (9)
C12—C11	1.395 (16)	C114—H11C	0.9600
C13—H13	0.9300	C114—H11D	0.9600
C13—C14	1.3900	C114—H11E	0.9600
C14—H14	0.9300	C112—H11F	0.9600
C23—H23	0.9300	C112—H11G	0.9600
C23—C24	1.398 (16)	C112—H11H	0.9600
C3—H3	0.9300	C112—C111	1.65 (8)
C3—C4	1.391 (16)	C111—H11I	0.9700
C82—H82A	0.9600	C111—H11J	0.9700
C82—H82B	0.9600	C115—H11K	0.9700
C82—H82C	0.9600	C115—H11L	0.9700
C36—C25	1.3900	C115—C116	1.57 (8)
C36—C29	1.3900	C116—H11M	0.9600
C25—C26	1.3900	C116—H11N	0.9600
C25—C24	1.399 (16)	C116—H11O	0.9600
Au1^i—Au2—Au1	180.0	C28—C29—C30	119 (3)
P1^i—Au2—Au1	85.4 (3)	P1—C83—H83A	106.2
P1—Au2—Au1^i	85.4 (3)	P1—C83—H83B	106.2
P1—Au2—Au1	94.6 (3)	H83A—C83—H83B	106.4
P1^i—Au2—Au1^i	94.6 (3)	C84—C83—P1	124 (4)
P1—Au2—P1^i	180.0 (3)	C84—C83—H83A	106.2
Au2—Au1—Au4	173.1 (2)	C84—C83—H83B	106.2
C19—Au1—Au2	95.0 (9)	O1—C17—C18	125 (4)
C19—Au1—C39	179.1 (18)	O1—C17—C1	126 (4)
C19—Au1—Au4	85.4 (10)	C18—C17—C1	110 (3)
C39—Au1—Au2	84.6 (12)	C23—C24—C25	120 (3)
C39—Au1—Au4	94.9 (12)	C23—C24—H24	119.8
C85—P1—Au2	103 (3)	C25—C24—H24	119.8
C85—P1—C83	116 (2)	C32—C31—H31	121.8
C81—P1—Au2	109.6 (18)	C30—C31—C32	116 (3)
C81—P1—C85	114 (3)	C30—C31—H31	121.8
C81—P1—C83	102 (4)	C83—C84—H84A	109.5
C83—P1—Au2	112.3 (15)	C83—C84—H84B	109.5
P1—C85—H85A	106.2	C83—C84—H84C	109.5
P1—C85—H85B	106.2	H84A—C84—H84B	109.5
H85A—C85—H85B	106.4	H84A—C84—H84C	109.5
C86—C85—P1	124 (5)	H84B—C84—H84C	109.5
C86—C85—H85A	106.2	C29—C30—H30	120.1
C86—C85—H85B	106.2	C31—C30—C29	120 (4)
C18—C19—Au1	174 (2)	C31—C30—H30	120.1
C21—C34—H34	120.0	C3—C4—H4	116.6
C21—C34—C33	120.0	C3—C4—C5	127 (4)
C33—C34—H34	120.0	C5—C4—H4	116.6
C34—C21—C22	120.0	C85—C86—H86A	109.5
C34—C21—C37	119 (2)	C85—C86—H86B	109.5
C22—C21—C37	121 (2)	C85—C86—H86C	109.5
C21—C22—C23	124 (2)	H86A—C86—H86B	109.5
C35—C22—C21	120.0	H86A—C86—H86C	109.5
C35—C22—C23	116 (2)	H86B—C86—H86C	109.5
C22—C35—C32	120.0	C6—C5—C4	127 (4)
C22—C35—C36	123.4 (17)	C6—C5—C16	120.0
C32—C35—C36	116.6 (17)	C16—C5—C4	112 (4)
C35—C32—C31	125 (2)	C5—C6—H6	120.0
C33—C32—C35	120.0	C5—C6—C7	120.0
C33—C32—C31	114 (2)	C7—C6—H6	120.0
C34—C33—H33	120.0	C6—C7—H7	120.0
C32—C33—C34	120.0	C8—C7—C6	120.0
C32—C33—H33	120.0	C8—C7—H7	120.0
P1—C81—H81A	108.1	C7—C8—H8	120.0
P1—C81—H81B	108.1	C7—C8—C9	120.0
H81A—C81—H81B	107.3	C9—C8—H8	120.0
C82—C81—P1	117 (4)	C8—C9—C10	112 (4)
C82—C81—H81A	108.1	C16—C9—C8	120.0
C82—C81—H81B	108.1	C16—C9—C10	128 (4)
C39—C38—C37	171 (6)	C5—C16—C15	125 (4)
C38—C39—Au1	174 (5)	C9—C16—C15	115 (4)
C19—C18—C17	156 (5)	C9—C16—C5	120.0
C2—C1—C14	120.0	C12—C11—H11	118.4
C2—C1—C17	127 (3)	C10—C11—C12	123 (3)
C14—C1—C17	113 (3)	C10—C11—H11	118.4
C1—C2—C3	120 (3)	C9—C10—H10	123.6
C15—C2—C1	120.0	C11—C10—C9	113 (4)
C15—C2—C3	120 (3)	C11—C10—H10	123.6
C2—C15—C12	120.0	P4—Au4—Au1	101.6 (5)
C2—C15—C16	119 (3)	C113—P4—Au4	105 (2)
C12—C15—C16	121 (3)	C111—P4—Au4	118.6 (14)
C15—C12—C11	120 (3)	C111—P4—C113	112 (3)
C13—C12—C15	120.0	C111—P4—C115	109 (4)
C13—C12—C11	120 (3)	C115—P4—Au4	101.2 (15)
C12—C13—H13	120.0	C115—P4—C113	110 (3)
C14—C13—C12	120.0	P4—C113—H11A	105.5
C14—C13—H13	120.0	P4—C113—H11B	105.5
C1—C14—H14	120.0	H11A—C113—H11B	106.1
C13—C14—C1	120.0	C114—C113—P4	127 (6)
C13—C14—H14	120.0	C114—C113—H11A	105.5
C22—C23—H23	119.0	C114—C113—H11B	105.5
C24—C23—C22	122 (3)	C113—C114—H11C	109.5
C24—C23—H23	119.0	C113—C114—H11D	109.5
C2—C3—H3	121.8	C113—C114—H11E	109.5
C4—C3—C2	116 (3)	H11C—C114—H11D	109.5
C4—C3—H3	121.8	H11C—C114—H11E	109.5
C81—C82—H82A	109.5	H11D—C114—H11E	109.5
C81—C82—H82B	109.5	H11F—C112—H11G	109.5
C81—C82—H82C	109.5	H11F—C112—H11H	109.5
H82A—C82—H82B	109.5	H11G—C112—H11H	109.5
H82A—C82—H82C	109.5	C111—C112—H11F	109.5
H82B—C82—H82C	109.5	C111—C112—H11G	109.5
O2—C37—C21	126 (4)	C111—C112—H11H	109.5
O2—C37—C38	119 (5)	P4—C111—H11I	109.1
C21—C37—C38	114 (3)	P4—C111—H11J	109.1
C25—C36—C35	120 (2)	C112—C111—P4	112 (3)
C25—C36—C29	120.0	C112—C111—H11I	109.1
C29—C36—C35	120 (2)	C112—C111—H11J	109.1
C36—C25—C24	119 (2)	H11I—C111—H11J	107.9
C26—C25—C36	120.0	P4—C115—H11K	107.9
C26—C25—C24	121 (2)	P4—C115—H11L	107.9
C25—C26—H26	120.0	H11K—C115—H11L	107.2
C25—C26—C27	120.0	C116—C115—P4	117 (4)
C27—C26—H26	120.0	C116—C115—H11K	107.9
C26—C27—H27	120.0	C116—C115—H11L	107.9
C28—C27—C26	120.0	C115—C116—H11M	109.5
C28—C27—H27	120.0	C115—C116—H11N	109.5
C27—C28—H28	120.0	C115—C116—H11O	109.5
C29—C28—C27	120.0	H11M—C116—H11N	109.5
C29—C28—H28	120.0	H11M—C116—H11O	109.5
C36—C29—C30	121 (3)	H11N—C116—H11O	109.5
C28—C29—C36	120.0
Au2—P1—C85—C86	−55 (5)	C14—C1—C17—C18	−25 (2)
Au2—P1—C81—C82	54 (5)	C23—C22—C35—C32	179.4 (4)
C85—P1—C81—C82	169 (5)	C23—C22—C35—C36	−1 (2)
C19—C18—C17—O1	−0.1 (8)	C3—C2—C15—C12	−179.7 (6)
C19—C18—C17—C1	−175 (5)	C3—C2—C15—C16	1 (2)
C34—C21—C22—C35	0.0	C3—C4—C5—C6	−178 (2)
C34—C21—C22—C23	−179.4 (4)	C3—C4—C5—C16	10 (4)
C34—C21—C37—O2	−167 (3)	C37—C21—C22—C35	−175 (3)
C34—C21—C37—C38	22 (4)	C37—C21—C22—C23	5 (2)
C21—C34—C33—C32	0.0	C36—C35—C32—C33	−179.2 (18)
C21—C22—C35—C32	0.0	C36—C35—C32—C31	−6 (2)
C21—C22—C35—C36	179.1 (19)	C36—C25—C26—C27	0.0
C21—C22—C23—C24	177.5 (19)	C36—C25—C24—C23	−4 (3)
C22—C21—C37—O2	9 (4)	C36—C29—C30—C31	5 (4)
C22—C21—C37—C38	−162 (2)	C25—C36—C29—C28	0.0
C22—C35—C32—C33	0.0	C25—C36—C29—C30	179 (2)
C22—C35—C32—C31	173 (2)	C25—C26—C27—C28	0.0
C22—C35—C36—C25	2 (3)	C26—C25—C24—C23	176 (2)
C22—C35—C36—C29	−177.2 (13)	C26—C27—C28—C29	0.0
C22—C23—C24—C25	4 (3)	C27—C28—C29—C36	0.0
C35—C22—C23—C24	−2 (2)	C27—C28—C29—C30	−179 (2)
C35—C32—C33—C34	0.0	C28—C29—C30—C31	−176 (3)
C35—C32—C31—C30	10 (4)	C29—C36—C25—C26	0.0
C35—C36—C25—C26	−179 (2)	C29—C36—C25—C24	180 (2)
C35—C36—C25—C24	0 (2)	C83—P1—C85—C86	68 (6)
C35—C36—C29—C28	179 (2)	C83—P1—C81—C82	−65 (5)
C35—C36—C29—C30	−2 (3)	C17—C1—C2—C15	173 (3)
C32—C35—C36—C25	−178.6 (10)	C17—C1—C2—C3	−7 (3)
C32—C35—C36—C29	2 (2)	C17—C1—C14—C13	−174 (3)
C32—C31—C30—C29	−9 (5)	C24—C25—C26—C27	−180 (2)
C33—C34—C21—C22	0.0	C31—C32—C33—C34	−174 (2)
C33—C34—C21—C37	175 (2)	C4—C5—C6—C7	−172 (4)
C33—C32—C31—C30	−177 (3)	C4—C5—C16—C15	−4 (3)
C81—P1—C85—C86	−174 (5)	C4—C5—C16—C9	173 (3)
C1—C2—C15—C12	0.0	C5—C6—C7—C8	0.0
C1—C2—C15—C16	−179 (2)	C6—C5—C16—C15	−177 (3)
C1—C2—C3—C4	−176.6 (19)	C6—C5—C16—C9	0.0
C2—C1—C14—C13	0.0	C6—C7—C8—C9	0.0
C2—C1—C17—O1	−14 (6)	C7—C8—C9—C16	0.0
C2—C1—C17—C18	161.6 (14)	C7—C8—C9—C10	180 (2)
C2—C15—C12—C13	0.0	C8—C9—C16—C15	178 (3)
C2—C15—C12—C11	178 (2)	C8—C9—C16—C5	0.0
C2—C15—C16—C5	−1 (3)	C8—C9—C10—C11	−179 (3)
C2—C15—C16—C9	−178.1 (14)	C16—C15—C12—C13	179 (2)
C2—C3—C4—C5	−9 (4)	C16—C15—C12—C11	−3 (2)
C15—C2—C3—C4	3.1 (18)	C16—C5—C6—C7	0.0
C15—C12—C13—C14	0.0	C16—C9—C10—C11	1 (4)
C15—C12—C11—C10	2 (4)	C11—C12—C13—C14	−178 (2)
C12—C15—C16—C5	−179.6 (11)	C10—C9—C16—C15	−2 (3)
C12—C15—C16—C9	3 (3)	C10—C9—C16—C5	−180 (3)
C12—C13—C14—C1	0.0	Au4—P4—C111—C112	−50 (5)
C12—C11—C10—C9	−1 (4)	Au4—P4—C115—C116	55 (4)
C13—C12—C11—C10	180 (3)	C113—P4—C111—C112	−174 (4)
C14—C1—C2—C15	0.0	C113—P4—C115—C116	166 (4)
C14—C1—C2—C3	179.7 (6)	C111—P4—C115—C116	−71 (4)
C14—C1—C17—O1	160 (3)	C115—P4—C111—C112	65 (4)

Symmetry code: (i) −x+1, −y+2, −z+1.

(crystal_4b)

Crystal data

C25H24AuOP	F(000) = 1104
Mr = 568.38	Dx = 1.941 Mg m^−3
Monoclinic, P21/c	Synchrotron radiation, λ = 0.41004 Å
a = 16.13 (4) Å	Cell parameters from 3884 reflections
b = 6.7304 (9) Å	θ = 2.0–21.5°
c = 18.096 (3) Å	µ = 1.87 mm^−1
β = 97.93 (8)°	T = 293 K
V = 1945 (5) Å^3	Prism, yellow
Z = 4	0.06 × 0.05 × 0.02 mm

Data collection

Esperanto-CrysAlisPro-abstract goniometer imported esperanto images diffractometer	2004 independent reflections
Radiation source: synchrotron	432 reflections with I > 2σ(I)
Synchrotron monochromator	Rint = 0.163
Detector resolution: 13.3333 pixels mm^-1	θmax = 21.5°, θmin = 2.0°
ω scans	h = −8→8
Absorption correction: multi-scan CrysAlisPro 1.171.42.49 (Rigaku Oxford Diffraction, 2022) Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm.	k = −10→11
Tmin = 0.129, Tmax = 1.000	l = −30→29
3884 measured reflections

Refinement

Refinement on F^2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F^2 > 2σ(F^2)] = 0.172	H-atom parameters constrained
wR(F^2) = 0.483	w = 1/[σ^2(Fo^2) + (0.2P)^2] where P = (Fo^2 + 2Fc^2)/3
S = 1.00	(Δ/σ)max < 0.001
2004 reflections	Δρmax = 1.15 e Å^−3
235 parameters	Δρmin = −0.91 e Å^−3
632 restraints

Special details

Experimental. High-pressure measurement at 0.8 GPa in a Membrane Diamond Anvil Cell with effective opening angle of 35 deg. and helium used as a pressure medium. Pressure determined by monitoring the shift of the ruby R1-fluorescence line.

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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Ų)

	x	y	z	Uiso*/Ueq
Au1	1.0000	0.5000	0.5000	0.085 (8)
Au2	1.0000	0.0000	0.5000	0.072 (7)
P1	1.064 (2)	0.002 (2)	0.3944 (7)	0.062 (7)
O1	0.790 (7)	0.558 (5)	0.2488 (16)	0.071 (7)
C17	0.784 (6)	0.589 (8)	0.317 (2)	0.060 (4)
C18	0.832 (4)	0.546 (7)	0.371 (2)	0.059 (5)
C19	0.889 (5)	0.540 (6)	0.418 (2)	0.055 (6)
C20	1.108 (9)	0.245 (7)	0.363 (3)	0.063 (8)
H20A	1.1072	0.2433	0.3090	0.076*
H20B	1.0730	0.3550	0.3749	0.076*
C21	1.198 (7)	0.272 (8)	0.402 (3)	0.081 (14)
H21A	1.2367	0.2335	0.3691	0.121*
H21B	1.2063	0.1899	0.4461	0.121*
H21C	1.2070	0.4085	0.4163	0.121*
C22	1.157 (6)	−0.171 (7)	0.398 (2)	0.061 (8)
H22A	1.1385	−0.3044	0.3837	0.074*
H22B	1.1947	−0.1262	0.3641	0.074*
C23	1.204 (9)	−0.174 (9)	0.479 (2)	0.076 (19)
H23A	1.2498	−0.2654	0.4819	0.115*
H23B	1.1660	−0.2141	0.5125	0.115*
H23C	1.2248	−0.0430	0.4919	0.115*
C24	0.981 (6)	−0.066 (8)	0.313 (2)	0.066 (8)
H24A	1.0058	−0.0523	0.2675	0.079*
H24B	0.9676	−0.2056	0.3181	0.079*
C25	0.899 (7)	0.053 (6)	0.304 (3)	0.061 (13)
H25A	0.8649	0.0153	0.2583	0.091*
H25B	0.9108	0.1921	0.3033	0.091*
H25C	0.8687	0.0242	0.3453	0.091*
C11	0.470 (4)	0.655 (4)	0.4199 (15)	0.059 (4)
H11	0.4696	0.6622	0.4712	0.071*
C10	0.394 (4)	0.651 (4)	0.3720 (19)	0.060 (4)
H10	0.3434	0.6550	0.3911	0.071*
C4	0.550 (4)	0.628 (4)	0.1628 (15)	0.058 (4)
H4	0.5508	0.6215	0.1115	0.069*
C3	0.622 (4)	0.630 (5)	0.2075 (19)	0.058 (4)
H3	0.6722	0.6265	0.1875	0.069*
C15	0.547 (3)	0.6411 (18)	0.3149 (12)	0.059 (4)
C12	0.545 (4)	0.649 (2)	0.3915 (13)	0.059 (4)
C13	0.619 (4)	0.651 (3)	0.4403 (10)	0.059 (4)
H13	0.6183	0.6560	0.4915	0.071*
C14	0.696 (4)	0.646 (3)	0.4127 (15)	0.059 (4)
H14	0.7456	0.6477	0.4454	0.071*
C1	0.697 (3)	0.639 (3)	0.3361 (16)	0.059 (4)
C2	0.623 (4)	0.636 (3)	0.2873 (11)	0.059 (4)
C16	0.471 (3)	0.640 (3)	0.2663 (12)	0.058 (4)
C5	0.472 (4)	0.635 (3)	0.1896 (12)	0.058 (4)
C6	0.397 (4)	0.631 (3)	0.1413 (11)	0.059 (4)
H6	0.3980	0.6279	0.0900	0.070*
C7	0.322 (4)	0.632 (4)	0.1697 (15)	0.060 (4)
H7	0.2715	0.6292	0.1375	0.071*
C8	0.321 (3)	0.637 (4)	0.2464 (16)	0.060 (4)
H8	0.2700	0.6373	0.2654	0.072*
C9	0.396 (4)	0.641 (3)	0.2947 (11)	0.060 (4)

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
Au1	0.09 (3)	0.086 (2)	0.078 (2)	0.014 (6)	0.010 (5)	−0.005 (2)
Au2	0.08 (2)	0.087 (2)	0.0523 (14)	0.020 (6)	0.015 (4)	0.005 (2)
P1	0.07 (2)	0.055 (6)	0.062 (5)	0.014 (13)	0.012 (10)	−0.016 (7)
O1	0.062 (7)	0.091 (17)	0.059 (4)	0.008 (7)	0.007 (3)	−0.002 (3)
C17	0.059 (4)	0.062 (7)	0.059 (4)	0.001 (3)	0.008 (2)	0.000 (3)
C18	0.059 (5)	0.058 (7)	0.059 (5)	0.000 (3)	0.008 (3)	−0.001 (3)
C19	0.056 (6)	0.054 (8)	0.056 (6)	0.000 (4)	0.010 (4)	−0.001 (4)
C20	0.07 (2)	0.056 (7)	0.062 (11)	0.013 (13)	0.010 (11)	−0.016 (8)
C21	0.08 (2)	0.074 (12)	0.088 (19)	0.003 (13)	−0.002 (11)	0.003 (13)
C22	0.07 (2)	0.056 (7)	0.058 (9)	0.015 (13)	0.012 (11)	−0.017 (8)
C23	0.08 (3)	0.08 (3)	0.060 (10)	0.04 (3)	0.007 (14)	−0.024 (13)
C24	0.07 (2)	0.058 (8)	0.066 (8)	0.013 (13)	0.007 (11)	−0.015 (8)
C25	0.07 (2)	0.046 (19)	0.067 (15)	0.006 (15)	0.013 (13)	−0.004 (14)
C11	0.059 (4)	0.059 (7)	0.059 (4)	0.000 (2)	0.008 (2)	0.000 (3)
C10	0.059 (4)	0.060 (7)	0.060 (4)	0.000 (2)	0.0081 (19)	0.000 (2)
C4	0.058 (4)	0.055 (7)	0.059 (4)	0.000 (2)	0.0076 (19)	0.000 (2)
C3	0.058 (4)	0.056 (7)	0.059 (4)	0.000 (2)	0.0077 (19)	0.000 (2)
C15	0.059 (4)	0.058 (7)	0.059 (4)	0.0000 (19)	0.0078 (17)	0.000 (2)
C12	0.059 (4)	0.059 (7)	0.059 (4)	0.000 (2)	0.0079 (17)	0.000 (2)
C13	0.059 (4)	0.059 (7)	0.059 (4)	0.000 (2)	0.0079 (19)	0.000 (2)
C14	0.059 (4)	0.059 (7)	0.059 (4)	0.000 (2)	0.0078 (19)	0.000 (2)
C1	0.059 (4)	0.059 (7)	0.059 (4)	0.000 (2)	0.0077 (18)	0.000 (2)
C2	0.059 (4)	0.060 (7)	0.059 (4)	0.000 (2)	0.0078 (17)	0.000 (2)
C16	0.059 (4)	0.056 (7)	0.059 (4)	0.0000 (19)	0.0078 (17)	0.000 (2)
C5	0.059 (4)	0.057 (7)	0.059 (4)	0.000 (2)	0.0078 (17)	0.000 (2)
C6	0.059 (4)	0.058 (7)	0.059 (4)	0.000 (2)	0.008 (2)	0.000 (3)
C7	0.059 (4)	0.059 (7)	0.060 (4)	0.000 (3)	0.008 (2)	0.000 (3)
C8	0.059 (4)	0.060 (7)	0.060 (4)	0.000 (2)	0.008 (2)	0.000 (3)
C9	0.059 (4)	0.060 (7)	0.060 (4)	0.000 (2)	0.0082 (18)	0.000 (2)

Geometric parameters (Å, º)

Au1—Au2	3.3652 (5)	C25—H25B	0.9600
Au1—Au2^i	3.3652 (5)	C25—H25C	0.9600
Au1—C19^ii	2.18 (6)	C11—H11	0.9300
Au1—C19	2.18 (6)	C11—C10	1.40 (5)
Au2—Au1^iii	3.3652 (5)	C11—C12	1.38 (4)
Au2—P1	2.29 (2)	C10—H10	0.9300
Au2—P1^iv	2.29 (2)	C10—C9	1.40 (3)
P1—C20	1.90 (6)	C4—H4	0.9300
P1—C22	1.90 (6)	C4—C3	1.32 (5)
P1—C24	1.90 (6)	C4—C5	1.41 (4)
O1—C17	1.26 (4)	C3—H3	0.9300
C17—C18	1.20 (6)	C3—C2	1.44 (3)
C17—C1	1.52 (11)	C15—C12	1.3900
C18—C19	1.16 (5)	C15—C2	1.3900
C20—H20A	0.9700	C15—C16	1.398 (19)
C20—H20B	0.9700	C12—C13	1.3900
C20—C21	1.54 (9)	C13—H13	0.9300
C21—H21A	0.9600	C13—C14	1.3900
C21—H21B	0.9600	C14—H14	0.9300
C21—H21C	0.9600	C14—C1	1.3900
C22—H22A	0.9700	C1—C2	1.3900
C22—H22B	0.9700	C16—C5	1.3900
C22—C23	1.54 (8)	C16—C9	1.3900
C23—H23A	0.9600	C5—C6	1.3900
C23—H23B	0.9600	C6—H6	0.9300
C23—H23C	0.9600	C6—C7	1.3900
C24—H24A	0.9700	C7—H7	0.9300
C24—H24B	0.9700	C7—C8	1.3900
C24—C25	1.54 (9)	C8—H8	0.9300
C25—H25A	0.9600	C8—C9	1.3900
Au2—Au1—Au2^i	180.0	C24—C25—H25B	109.5
C19^ii—Au1—Au2^i	97.0 (12)	C24—C25—H25C	109.5
C19^ii—Au1—Au2	83.0 (12)	H25A—C25—H25B	109.5
C19—Au1—Au2	97.0 (12)	H25A—C25—H25C	109.5
C19—Au1—Au2^i	83.0 (12)	H25B—C25—H25C	109.5
C19^ii—Au1—C19	179.998 (11)	C10—C11—H11	119.8
Au1—Au2—Au1^iii	180.0	C12—C11—H11	119.8
P1—Au2—Au1^iii	90.4 (4)	C12—C11—C10	120.3 (19)
P1—Au2—Au1	89.6 (4)	C11—C10—H10	120.5
P1^iv—Au2—Au1^iii	89.6 (4)	C11—C10—C9	119 (2)
P1^iv—Au2—Au1	90.4 (4)	C9—C10—H10	120.5
P1^iv—Au2—P1	180.0 (7)	C3—C4—H4	118.7
C20—P1—Au2	119 (2)	C3—C4—C5	123 (2)
C20—P1—C24	103 (4)	C5—C4—H4	118.7
C22—P1—Au2	114.2 (18)	C4—C3—H3	120.0
C22—P1—C20	103 (5)	C4—C3—C2	120 (2)
C22—P1—C24	110 (3)	C2—C3—H3	120.0
C24—P1—Au2	107 (3)	C12—C15—C2	120.0
O1—C17—C1	117 (7)	C12—C15—C16	119.5 (12)
C18—C17—O1	129 (8)	C2—C15—C16	120.5 (12)
C18—C17—C1	112 (5)	C11—C12—C15	121 (2)
C19—C18—C17	165 (7)	C11—C12—C13	119 (2)
C18—C19—Au1	174 (5)	C13—C12—C15	120.0
P1—C20—H20A	109.9	C12—C13—H13	120.0
P1—C20—H20B	109.9	C14—C13—C12	120.0
H20A—C20—H20B	108.3	C14—C13—H13	120.0
C21—C20—P1	109 (5)	C13—C14—H14	120.0
C21—C20—H20A	109.9	C13—C14—C1	120.0
C21—C20—H20B	109.9	C1—C14—H14	120.0
C20—C21—H21A	109.5	C14—C1—C17	113 (3)
C20—C21—H21B	109.5	C14—C1—C2	120.0
C20—C21—H21C	109.5	C2—C1—C17	126 (3)
H21A—C21—H21B	109.5	C15—C2—C3	118.3 (18)
H21A—C21—H21C	109.5	C1—C2—C3	121.7 (18)
H21B—C21—H21C	109.5	C1—C2—C15	120.0
P1—C22—H22A	109.9	C5—C16—C15	120.1 (12)
P1—C22—H22B	109.9	C5—C16—C9	120.0
H22A—C22—H22B	108.3	C9—C16—C15	119.9 (12)
C23—C22—P1	109 (5)	C16—C5—C4	118.5 (19)
C23—C22—H22A	109.9	C16—C5—C6	120.0
C23—C22—H22B	109.9	C6—C5—C4	121.4 (19)
C22—C23—H23A	109.5	C5—C6—H6	120.0
C22—C23—H23B	109.5	C5—C6—C7	120.0
C22—C23—H23C	109.5	C7—C6—H6	120.0
H23A—C23—H23B	109.5	C6—C7—H7	120.0
H23A—C23—H23C	109.5	C8—C7—C6	120.0
H23B—C23—H23C	109.5	C8—C7—H7	120.0
P1—C24—H24A	107.9	C7—C8—H8	120.0
P1—C24—H24B	107.9	C7—C8—C9	120.0
H24A—C24—H24B	107.2	C9—C8—H8	120.0
C25—C24—P1	117 (4)	C16—C9—C10	120.4 (19)
C25—C24—H24A	107.9	C8—C9—C10	119.6 (19)
C25—C24—H24B	107.9	C8—C9—C16	120.0
C24—C25—H25A	109.5
Au2—P1—C20—C21	87 (6)	C12—C15—C2—C3	−179.7 (13)
Au2—P1—C22—C23	−36 (6)	C12—C15—C2—C1	0.0
O1—C17—C18—C19	72 (27)	C12—C15—C16—C5	179.2 (7)
O1—C17—C1—C14	173 (4)	C12—C15—C16—C9	−1.8 (14)
O1—C17—C1—C2	6 (6)	C12—C13—C14—C1	0.0
C17—C1—C2—C3	−15 (3)	C13—C14—C1—C17	−167 (3)
C17—C1—C2—C15	166 (3)	C13—C14—C1—C2	0.0
C18—C17—C1—C14	7 (6)	C14—C1—C2—C3	179.7 (13)
C18—C17—C1—C2	−160 (4)	C14—C1—C2—C15	0.0
C20—P1—C22—C23	94 (6)	C1—C17—C18—C19	−124 (25)
C22—P1—C20—C21	−40 (4)	C2—C15—C12—C11	179.5 (14)
C24—P1—C20—C21	−155 (5)	C2—C15—C12—C13	0.0
C24—P1—C22—C23	−156 (6)	C2—C15—C16—C5	−0.3 (14)
C11—C10—C9—C16	−2 (3)	C2—C15—C16—C9	178.6 (8)
C11—C10—C9—C8	180 (2)	C16—C15—C12—C11	0.0 (16)
C11—C12—C13—C14	−179.5 (14)	C16—C15—C12—C13	−179.5 (9)
C10—C11—C12—C15	1 (3)	C16—C15—C2—C3	−0.2 (15)
C10—C11—C12—C13	−179.5 (19)	C16—C15—C2—C1	179.5 (9)
C4—C3—C2—C15	0 (3)	C16—C5—C6—C7	0.0
C4—C3—C2—C1	−180 (2)	C5—C4—C3—C2	1 (4)
C4—C5—C6—C7	178 (2)	C5—C16—C9—C10	−178 (2)
C3—C4—C5—C16	−1 (3)	C5—C16—C9—C8	0.0
C3—C4—C5—C6	−179 (2)	C5—C6—C7—C8	0.0
C15—C12—C13—C14	0.0	C6—C7—C8—C9	0.0
C15—C16—C5—C4	1.1 (19)	C7—C8—C9—C10	178 (2)
C15—C16—C5—C6	179.0 (16)	C7—C8—C9—C16	0.0
C15—C16—C9—C10	3 (2)	C9—C16—C5—C4	−178 (2)
C15—C16—C9—C8	−179.0 (16)	C9—C16—C5—C6	0.0
C12—C11—C10—C9	0 (4)

Symmetry codes: (i) x, y+1, z; (ii) −x+2, −y+1, −z+1; (iii) x, y−1, z; (iv) −x+2, −y, −z+1.

(crystal_5)

Crystal data

C25H24AuOP	F(000) = 1102.600
Mr = 568.41	Dx = 1.990 Mg m^−3
Monoclinic, P21/c	Synchrotron radiation, λ = 0.41097 Å
a = 16.0966 (4) Å	Cell parameters from 597 reflections
b = 6.62840 (13) Å	θ = 2.1–18.7°
c = 17.9473 (14) Å	µ = 1.93 mm^−1
β = 97.886 (6)°	T = 293 K
V = 1896.77 (16) Å^3	Block, clear yellow
Z = 4	0.26 × 0.18 × 0.11 mm

Data collection

Synchrotron diffractometer	1955 reflections with I ≥ 2u(I)
π scans	Rint = 0.059
Absorption correction: multi-scan CrysAlisPro, Agilent Technologies, Version 1.171.37.34 (release 22-05-2014 CrysAlis171 .NET) (compiled May 22 2014,16:03:01) Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm.	θmax = 18.1°, θmin = 1.9°
Tmin = 0.839, Tmax = 1.000	h = −26→25
3932 measured reflections	k = 0→11
3740 independent reflections	l = 0→27

Refinement

Refinement on F^2	0 restraints
Least-squares matrix: full	39 constraints
R[F^2 > 2σ(F^2)] = 0.055	H-atom parameters constrained
wR(F^2) = 0.229	w = 1/[σ^2(Fo^2) + (0.1273P)^2 + 1.6491P] where P = (Fo^2 + 2Fc^2)/3
S = 1.02	(Δ/σ)max = 0.001
3740 reflections	Δρmax = 2.34 e Å^−3
256 parameters	Δρmin = −2.10 e Å^−3

Special details

Experimental. High-pressure measurement at 1.1 GPa in a MB DAC with effective opening angle of 30 deg. and Paratone oil used as a pressure medium. Pressure determined by monitoring the shift of the ruby R1-fluorescence line.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Ų)

	x	y	z	Uiso*/Ueq
Au1	1.0	0.5	0.5	0.0331 (2)
Au2	1.0	0.0	0.5	0.0311 (2)
P1	1.06467 (9)	0.00311 (18)	0.39305 (11)	0.0324 (4)
O1	0.7869 (3)	0.5691 (11)	0.2454 (4)	0.0720 (15)
C3	0.6132 (4)	0.6429 (8)	0.2032 (4)	0.0393 (15)
H3	0.6710 (4)	0.6378 (8)	0.1787 (4)	0.0472 (18)*
C4	0.5380 (4)	0.6492 (9)	0.1577 (4)	0.0422 (14)
H4	0.5377 (4)	0.6567 (9)	0.0973 (4)	0.0506 (17)*
C9	0.3833 (3)	0.6491 (9)	0.2961 (4)	0.0419 (16)
C16	0.4614 (3)	0.6519 (8)	0.2655 (4)	0.0353 (13)
C5	0.4600 (3)	0.6462 (8)	0.1864 (4)	0.0341 (13)
C6	0.3835 (4)	0.6440 (8)	0.1395 (4)	0.0458 (16)
H6	0.3830 (4)	0.6465 (8)	0.0791 (4)	0.0550 (19)*
C7	0.3079 (4)	0.6387 (11)	0.1685 (5)	0.054 (2)
H7	0.2491 (4)	0.6315 (11)	0.1311 (5)	0.065 (3)*
C8	0.3083 (4)	0.6425 (9)	0.2463 (5)	0.0499 (17)
H8	0.2492 (4)	0.6404 (9)	0.2688 (5)	0.060 (2)*
C10	0.3855 (4)	0.6616 (9)	0.3762 (4)	0.0462 (16)
H10	0.3271 (4)	0.6652 (9)	0.3998 (4)	0.0555 (19)*
C11	0.4590 (4)	0.6690 (9)	0.4229 (4)	0.0465 (15)
H11	0.4587 (4)	0.6811 (9)	0.4831 (4)	0.0558 (18)*
C12	0.5367 (4)	0.6610 (8)	0.3938 (4)	0.0390 (14)
C13	0.6137 (4)	0.6628 (9)	0.4420 (4)	0.0493 (16)
H13	0.6141 (4)	0.6776 (9)	0.5021 (4)	0.059 (2)*
C14	0.6883 (3)	0.6458 (9)	0.4130 (4)	0.0402 (14)
H14	0.7463 (3)	0.6442 (9)	0.4515 (4)	0.0483 (17)*
C1	0.6920 (4)	0.6304 (9)	0.3355 (4)	0.0401 (15)
C2	0.6159 (3)	0.6429 (8)	0.2850 (4)	0.0325 (12)
C15	0.5385 (3)	0.6522 (7)	0.3143 (4)	0.0322 (13)
C17	0.7750 (3)	0.5931 (10)	0.3119 (4)	0.0457 (16)
C18	0.8444 (3)	0.5686 (11)	0.3715 (5)	0.0486 (16)
C19	0.9054 (4)	0.5397 (10)	0.4200 (5)	0.0448 (16)
C20	1.1041 (4)	0.2425 (8)	0.3620 (5)	0.0480 (18)
H20a	1.1110 (4)	0.2296 (8)	0.3025 (5)	0.058 (2)*
H20b	1.0574 (4)	0.3590 (8)	0.3670 (5)	0.058 (2)*
C21	1.1879 (4)	0.3115 (11)	0.4050 (5)	0.0522 (17)
H21a	1.2057 (4)	0.4533 (11)	0.3826 (5)	0.078 (3)*
H21b	1.1817 (4)	0.3295 (11)	0.4636 (5)	0.078 (3)*
H21c	1.2353 (4)	0.2001 (11)	0.3991 (5)	0.078 (3)*
C22	1.1505 (4)	−0.1724 (10)	0.4016 (4)	0.0477 (17)
H22a	1.1256 (4)	−0.3245 (10)	0.3914 (4)	0.057 (2)*
H22b	1.1900 (4)	−0.1390 (10)	0.3584 (4)	0.057 (2)*
C23	1.2052 (4)	−0.1667 (11)	0.4799 (4)	0.0527 (17)
H23a	1.2553 (4)	−0.2751 (11)	0.4812 (4)	0.079 (3)*
H23b	1.2313 (4)	−0.0180 (11)	0.4899 (4)	0.079 (3)*
H23c	1.1671 (4)	−0.2032 (11)	0.5229 (4)	0.079 (3)*
C24	0.9934 (4)	−0.0735 (11)	0.3106 (4)	0.0466 (15)
H24a	1.0227 (4)	−0.0455 (11)	0.2603 (4)	0.0559 (18)*
H24b	0.9813 (4)	−0.2350 (11)	0.3137 (4)	0.0559 (18)*
C25	0.9102 (4)	0.0412 (11)	0.3047 (5)	0.0531 (19)
H25a	0.8696 (4)	−0.0079 (11)	0.2553 (5)	0.080 (3)*
H25b	0.8807 (4)	0.0118 (11)	0.3539 (5)	0.080 (3)*
H25c	0.9219 (4)	0.2006 (11)	0.3007 (5)	0.080 (3)*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
Au1	0.0226 (2)	0.0470 (3)	0.0305 (4)	0.00229 (9)	0.0064 (3)	−0.00200 (11)
Au2	0.0277 (3)	0.0493 (3)	0.0177 (3)	0.00047 (9)	0.0088 (3)	0.00023 (10)
P1	0.0335 (7)	0.0458 (9)	0.0197 (10)	−0.0005 (5)	0.0100 (8)	0.0001 (5)
O1	0.042 (2)	0.134 (5)	0.043 (4)	−0.003 (3)	0.015 (3)	−0.005 (4)
C3	0.049 (3)	0.046 (3)	0.025 (4)	−0.005 (3)	0.013 (4)	0.001 (2)
C4	0.046 (3)	0.058 (3)	0.023 (4)	0.003 (3)	0.006 (3)	0.002 (2)
C9	0.037 (3)	0.049 (3)	0.041 (5)	0.004 (2)	0.011 (4)	0.004 (3)
C16	0.037 (2)	0.040 (3)	0.029 (4)	0.006 (2)	0.004 (3)	−0.001 (2)
C5	0.037 (2)	0.035 (3)	0.029 (4)	0.002 (2)	−0.001 (3)	0.004 (2)
C6	0.055 (3)	0.048 (3)	0.032 (4)	0.001 (3)	−0.002 (4)	0.009 (2)
C7	0.043 (3)	0.068 (4)	0.044 (6)	0.006 (3)	−0.017 (4)	−0.004 (3)
C8	0.042 (3)	0.047 (3)	0.059 (5)	0.001 (2)	0.001 (4)	0.002 (3)
C10	0.039 (3)	0.057 (4)	0.044 (5)	0.004 (3)	0.010 (4)	−0.008 (3)
C11	0.055 (3)	0.059 (4)	0.031 (4)	0.003 (3)	0.025 (4)	0.004 (3)
C12	0.045 (3)	0.047 (3)	0.027 (4)	−0.002 (2)	0.014 (3)	0.001 (2)
C13	0.052 (3)	0.064 (4)	0.029 (4)	−0.006 (3)	−0.004 (4)	−0.002 (3)
C14	0.036 (2)	0.068 (4)	0.016 (3)	0.000 (2)	0.002 (3)	0.000 (2)
C1	0.042 (3)	0.056 (4)	0.023 (4)	−0.005 (3)	0.010 (3)	−0.002 (2)
C2	0.034 (2)	0.044 (3)	0.020 (3)	0.001 (2)	0.007 (3)	0.005 (2)
C15	0.035 (2)	0.034 (3)	0.028 (4)	−0.002 (2)	0.005 (3)	0.000 (2)
C17	0.033 (3)	0.061 (4)	0.043 (5)	−0.006 (3)	0.005 (3)	0.000 (3)
C18	0.032 (3)	0.068 (4)	0.048 (5)	0.002 (3)	0.013 (3)	0.002 (4)
C19	0.033 (3)	0.074 (4)	0.032 (4)	0.002 (3)	0.021 (3)	0.003 (3)
C20	0.052 (4)	0.045 (4)	0.049 (5)	0.002 (2)	0.017 (4)	0.006 (3)
C21	0.047 (3)	0.058 (4)	0.050 (5)	−0.008 (3)	0.000 (4)	0.000 (4)
C22	0.048 (3)	0.055 (4)	0.042 (5)	0.018 (3)	0.014 (4)	0.004 (3)
C23	0.052 (3)	0.068 (4)	0.037 (5)	0.007 (3)	0.004 (4)	0.010 (3)
C24	0.055 (3)	0.061 (4)	0.027 (4)	0.002 (3)	0.016 (3)	−0.014 (3)
C25	0.033 (3)	0.079 (4)	0.046 (5)	0.009 (3)	0.000 (4)	−0.004 (4)

Geometric parameters (Å, º)

Au1—Au2	3.3142	C12—C13	1.411 (8)
Au1—Au2^i	3.3142	C12—C15	1.432 (9)
Au1—C19	1.962 (8)	C13—H13	1.0830
Au1—C19^ii	1.962 (8)	C13—C14	1.376 (9)
Au2—P1^iii	2.3057 (18)	C14—H14	1.0830
Au2—P1	2.3057 (18)	C14—C1	1.405 (9)
P1—C20	1.825 (6)	C1—C2	1.422 (8)
P1—C22	1.796 (6)	C1—C17	1.476 (8)
P1—C24	1.816 (7)	C2—C15	1.419 (8)
O1—C17	1.245 (9)	C17—C18	1.446 (9)
C3—H3	1.0830	C18—C19	1.235 (9)
C3—C4	1.365 (8)	C20—H20a	1.0910
C3—C2	1.463 (9)	C20—H20b	1.0910
C4—H4	1.0830	C20—C21	1.529 (9)
C4—C5	1.421 (9)	C21—H21a	1.0770
C9—C16	1.438 (8)	C21—H21b	1.0770
C9—C8	1.401 (9)	C21—H21c	1.0770
C9—C10	1.436 (10)	C22—H22a	1.0910
C16—C5	1.419 (9)	C22—H22b	1.0910
C16—C15	1.417 (8)	C22—C23	1.553 (10)
C5—C6	1.393 (8)	C23—H23a	1.0770
C6—H6	1.0830	C23—H23b	1.0770
C6—C7	1.388 (10)	C23—H23c	1.0770
C7—H7	1.0830	C24—H24a	1.0910
C7—C8	1.397 (11)	C24—H24b	1.0910
C8—H8	1.0830	C24—C25	1.530 (8)
C10—H10	1.0830	C25—H25a	1.0770
C10—C11	1.355 (9)	C25—H25b	1.0770
C11—H11	1.0830	C25—H25c	1.0770
C11—C12	1.422 (9)
Au2^i—Au1—Au2	180.0	H14—C14—C13	118.7 (4)
C19^ii—Au1—Au2^i	97.7 (2)	C1—C14—C13	122.5 (6)
C19^ii—Au1—Au2	82.3 (2)	C1—C14—H14	118.7 (3)
C19—Au1—Au2	97.7 (2)	C2—C1—C14	118.5 (5)
C19—Au1—Au2^i	82.3 (2)	C17—C1—C14	117.4 (6)
C19^ii—Au1—C19	180.0	C17—C1—C2	124.1 (6)
Au1—Au2—Au1^iv	180.0	C1—C2—C3	123.0 (5)
P1^iii—Au2—Au1^iv	89.49 (3)	C15—C2—C3	117.7 (5)
P1^iii—Au2—Au1	90.51 (3)	C15—C2—C1	119.3 (6)
P1—Au2—Au1^iv	90.51 (3)	C12—C15—C16	118.7 (5)
P1—Au2—Au1	89.49 (3)	C2—C15—C16	120.7 (6)
P1^iii—Au2—P1	180.0	C2—C15—C12	120.6 (5)
C20—P1—Au2	118.6 (3)	C1—C17—O1	124.1 (6)
C22—P1—Au2	110.6 (3)	C18—C17—O1	119.3 (5)
C22—P1—C20	107.1 (3)	C18—C17—C1	116.4 (6)
C24—P1—Au2	111.6 (2)	C19—C18—C17	176.5 (7)
C24—P1—C20	101.6 (4)	C18—C19—Au1	177.6 (6)
C24—P1—C22	106.3 (3)	H20a—C20—P1	108.5 (3)
C4—C3—H3	119.9 (4)	H20b—C20—P1	108.5 (2)
C2—C3—H3	119.9 (3)	H20b—C20—H20a	107.5
C2—C3—C4	120.2 (6)	C21—C20—P1	115.2 (5)
H4—C4—C3	118.7 (4)	C21—C20—H20a	108.5 (4)
C5—C4—C3	122.5 (7)	C21—C20—H20b	108.5 (4)
C5—C4—H4	118.7 (4)	H21a—C21—C20	109.5
C8—C9—C16	118.6 (7)	H21b—C21—C20	109.5
C10—C9—C16	118.6 (6)	H21b—C21—H21a	109.5
C10—C9—C8	122.7 (6)	H21c—C21—C20	109.5
C5—C16—C9	119.2 (5)	H21c—C21—H21a	109.5
C15—C16—C9	120.1 (6)	H21c—C21—H21b	109.5
C15—C16—C5	120.7 (5)	H22a—C22—P1	108.9 (2)
C16—C5—C4	118.0 (5)	H22b—C22—P1	108.9 (3)
C6—C5—C4	122.2 (7)	H22b—C22—H22a	107.7
C6—C5—C16	119.8 (6)	C23—C22—P1	113.3 (5)
H6—C6—C5	119.3 (4)	C23—C22—H22a	108.9 (4)
C7—C6—C5	121.5 (7)	C23—C22—H22b	108.9 (4)
C7—C6—H6	119.3 (4)	H23a—C23—C22	109.5
H7—C7—C6	120.3 (4)	H23b—C23—C22	109.5
C8—C7—C6	119.3 (6)	H23b—C23—H23a	109.5
C8—C7—H7	120.3 (4)	H23c—C23—C22	109.5
C7—C8—C9	121.6 (7)	H23c—C23—H23a	109.5
H8—C8—C9	119.2 (4)	H23c—C23—H23b	109.5
H8—C8—C7	119.2 (4)	H24a—C24—P1	109.3 (2)
H10—C10—C9	119.3 (3)	H24b—C24—P1	109.3 (3)
C11—C10—C9	121.4 (6)	H24b—C24—H24a	108.0
C11—C10—H10	119.3 (4)	C25—C24—P1	111.5 (5)
H11—C11—C10	119.7 (4)	C25—C24—H24a	109.3 (4)
C12—C11—C10	120.6 (7)	C25—C24—H24b	109.3 (4)
C12—C11—H11	119.7 (4)	H25a—C25—C24	109.5
C13—C12—C11	121.1 (7)	H25b—C25—C24	109.5
C15—C12—C11	120.5 (6)	H25b—C25—H25a	109.5
C15—C12—C13	118.4 (5)	H25c—C25—C24	109.5
H13—C13—C12	119.8 (4)	H25c—C25—H25a	109.5
C14—C13—C12	120.4 (7)	H25c—C25—H25b	109.5
C14—C13—H13	119.8 (4)
O1—C17—C1—C14	177.4 (7)	C16—C5—C6—C7	−2.8 (6)
O1—C17—C1—C2	0.1 (8)	C16—C15—C12—C11	0.1 (6)
C3—C4—C5—C16	4.7 (6)	C16—C15—C12—C13	−179.5 (5)
C3—C4—C5—C6	−177.2 (5)	C16—C15—C2—C1	−176.0 (5)
C3—C2—C1—C14	175.6 (5)	C5—C6—C7—C8	2.2 (6)
C3—C2—C1—C17	−7.2 (6)	C10—C11—C12—C13	−178.2 (6)
C3—C2—C15—C16	2.8 (6)	C10—C11—C12—C15	2.2 (7)
C3—C2—C15—C12	−177.5 (5)	C11—C12—C13—C14	177.1 (6)
C4—C5—C16—C9	−180.0 (5)	C11—C12—C15—C2	−179.6 (5)
C4—C5—C16—C15	−2.5 (5)	C12—C13—C14—C1	1.4 (7)
C4—C5—C6—C7	179.2 (6)	C12—C15—C2—C1	3.7 (6)
C9—C16—C5—C6	1.9 (6)	C13—C14—C1—C2	3.2 (7)
C9—C16—C15—C12	−3.4 (6)	C13—C14—C1—C17	−174.2 (6)
C9—C16—C15—C2	176.2 (5)	C14—C1—C2—C15	−5.6 (7)
C9—C8—C7—C6	−0.8 (7)	C14—C1—C17—C18	2.2 (7)
C9—C10—C11—C12	−1.1 (7)

Symmetry codes: (i) x, y+1, z; (ii) −x+2, −y+1, −z+1; (iii) −x+2, −y, −z+1; (iv) x, y−1, z.