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Structure–property relationship of a complex photoluminescent arylacetylide-gold(I) compound. I: a pressure-induced phase transformation caught in the act
aBiological and Chemical Research Centre, Faculty of Chemistry, University of Warsaw, Żwirki i Wigury 101, 02-089 Warszawa, Poland, bLaboratory for Quantum Magnetism, École Polytechnique Fédérale de Lausanne, CH-1015 Lausanne, Switzerland, cALBA Synchrotron BL31-FaXToR, Cerdanyola del Vallés, Cataluña, Spain, and dMolecular Biophysics and Integrated Bioimaging Division, Lawrence Berkeley National Laboratory, 1 Cyclotron Road, Berkeley, CA 94720, USA
*Correspondence e-mail: dtchon@lbl.gov, am.makal@uw.edu.pl
A pressure-induced triclinic-to-monoclinic
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 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 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 (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 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 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 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 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 (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 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 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 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 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 for phase transition
The 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 ![]() |
In order to illustrate the 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 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 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 ). 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 P21/c. This result has been corroborated by the model obtained from unrestricted structure solution and against high-coverage multi-crystal data collected at 1.10 (3) GPa.
|
Based on these observations, the actual onset of a pressure-induced i.e. more thermodynamically favorable) unit-cell volume.
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 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 (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 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 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 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 of pyrEt-α in the high-pressure phase
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 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 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.
for pyrEt-4. Conclusions
We have successfully characterized a particular pressure-induced symmetry-increasing SCSC 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 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 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.
occurring in the of a large metalorganic gold(I) compound (pyrEt) in itsMoreover, 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
with an aspherical 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 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 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
https://doi.org/10.1107/S2052252524007681/lt5070sup1.cif
contains datablocks crystal_1, crystal_4a, crystal_4b, crystal_5. DOI:Supporting figures and tables. DOI: https://doi.org/10.1107/S2052252524007681/lt5070sup2.pdf
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) Å3 | 0.29 × 0.21 × 0.11 mm |
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 on F2 | 32 restraints |
Least-squares matrix: full | Hydrogen site location: inferred from neighbouring sites |
R[F2 > 2σ(F2)] = 0.040 | H-atom parameters constrained |
wR(F2) = 0.082 | w = 1/[σ2(Fo2) + (0.024P)2 + 1.6049P] where P = (Fo2 + 2Fc2)/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 |
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. |
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) |
U11 | U22 | U33 | U12 | U13 | U23 | |
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) |
Au2—Au1i | 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—P1i | 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 | ||
Au1i—Au2—Au1 | 180.0 | H86B—C86—H86C | 109.5 |
P1—Au2—Au1i | 86.43 (3) | C29—C28—H28 | 119.3 |
P1i—Au2—Au1 | 86.42 (3) | C27—C28—C29 | 121.3 (5) |
P1i—Au2—Au1i | 93.58 (3) | C27—C28—H28 | 119.3 |
P1—Au2—Au1 | 93.57 (3) | C4—C5—C16 | 117.6 (5) |
P1—Au2—P1i | 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. |
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) Å3 | 0.06 × 0.05 × 0.02 mm |
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 on F2 | 279 restraints |
Least-squares matrix: full | Hydrogen site location: inferred from neighbouring sites |
R[F2 > 2σ(F2)] = 0.123 | H-atom parameters constrained |
wR(F2) = 0.368 | w = 1/[σ2(Fo2) + (0.1727P)2] where P = (Fo2 + 2Fc2)/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 |
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. |
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* |
U11 | U22 | U33 | U12 | U13 | U23 | |
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) |
Au2—Au1 | 3.2197 (19) | C26—H26 | 0.9300 |
Au2—Au1i | 3.2197 (19) | C26—C27 | 1.3900 |
Au2—P1i | 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 |
Au1i—Au2—Au1 | 180.0 | C28—C29—C30 | 119 (3) |
P1i—Au2—Au1 | 85.4 (3) | P1—C83—H83A | 106.2 |
P1—Au2—Au1i | 85.4 (3) | P1—C83—H83B | 106.2 |
P1—Au2—Au1 | 94.6 (3) | H83A—C83—H83B | 106.4 |
P1i—Au2—Au1i | 94.6 (3) | C84—C83—P1 | 124 (4) |
P1—Au2—P1i | 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. |
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) Å3 | Prism, yellow |
Z = 4 | 0.06 × 0.05 × 0.02 mm |
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 on F2 | Primary atom site location: structure-invariant direct methods |
Least-squares matrix: full | Hydrogen site location: inferred from neighbouring sites |
R[F2 > 2σ(F2)] = 0.172 | H-atom parameters constrained |
wR(F2) = 0.483 | w = 1/[σ2(Fo2) + (0.2P)2] where P = (Fo2 + 2Fc2)/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 |
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. |
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) |
U11 | U22 | U33 | U12 | U13 | U23 | |
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) |
Au1—Au2 | 3.3652 (5) | C25—H25B | 0.9600 |
Au1—Au2i | 3.3652 (5) | C25—H25C | 0.9600 |
Au1—C19ii | 2.18 (6) | C11—H11 | 0.9300 |
Au1—C19 | 2.18 (6) | C11—C10 | 1.40 (5) |
Au2—Au1iii | 3.3652 (5) | C11—C12 | 1.38 (4) |
Au2—P1 | 2.29 (2) | C10—H10 | 0.9300 |
Au2—P1iv | 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—Au2i | 180.0 | C24—C25—H25B | 109.5 |
C19ii—Au1—Au2i | 97.0 (12) | C24—C25—H25C | 109.5 |
C19ii—Au1—Au2 | 83.0 (12) | H25A—C25—H25B | 109.5 |
C19—Au1—Au2 | 97.0 (12) | H25A—C25—H25C | 109.5 |
C19—Au1—Au2i | 83.0 (12) | H25B—C25—H25C | 109.5 |
C19ii—Au1—C19 | 179.998 (11) | C10—C11—H11 | 119.8 |
Au1—Au2—Au1iii | 180.0 | C12—C11—H11 | 119.8 |
P1—Au2—Au1iii | 90.4 (4) | C12—C11—C10 | 120.3 (19) |
P1—Au2—Au1 | 89.6 (4) | C11—C10—H10 | 120.5 |
P1iv—Au2—Au1iii | 89.6 (4) | C11—C10—C9 | 119 (2) |
P1iv—Au2—Au1 | 90.4 (4) | C9—C10—H10 | 120.5 |
P1iv—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. |
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) Å3 | Block, clear yellow |
Z = 4 | 0.26 × 0.18 × 0.11 mm |
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 on F2 | 0 restraints |
Least-squares matrix: full | 39 constraints |
R[F2 > 2σ(F2)] = 0.055 | H-atom parameters constrained |
wR(F2) = 0.229 | w = 1/[σ2(Fo2) + (0.1273P)2 + 1.6491P] where P = (Fo2 + 2Fc2)/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 |
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. |
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)* |
U11 | U22 | U33 | U12 | U13 | U23 | |
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) |
Au1—Au2 | 3.3142 | C12—C13 | 1.411 (8) |
Au1—Au2i | 3.3142 | C12—C15 | 1.432 (9) |
Au1—C19 | 1.962 (8) | C13—H13 | 1.0830 |
Au1—C19ii | 1.962 (8) | C13—C14 | 1.376 (9) |
Au2—P1iii | 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) | ||
Au2i—Au1—Au2 | 180.0 | H14—C14—C13 | 118.7 (4) |
C19ii—Au1—Au2i | 97.7 (2) | C1—C14—C13 | 122.5 (6) |
C19ii—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—Au2i | 82.3 (2) | C17—C1—C14 | 117.4 (6) |
C19ii—Au1—C19 | 180.0 | C17—C1—C2 | 124.1 (6) |
Au1—Au2—Au1iv | 180.0 | C1—C2—C3 | 123.0 (5) |
P1iii—Au2—Au1iv | 89.49 (3) | C15—C2—C3 | 117.7 (5) |
P1iii—Au2—Au1 | 90.51 (3) | C15—C2—C1 | 119.3 (6) |
P1—Au2—Au1iv | 90.51 (3) | C12—C15—C16 | 118.7 (5) |
P1—Au2—Au1 | 89.49 (3) | C2—C15—C16 | 120.7 (6) |
P1iii—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. |
Acknowledgements
The authors thank Damian Plażuk from the University of Łódź for providing the pyrEt-α substrate. The European Synchrotron Radiation Facility is acknowledged for provision of beam time on ID15B beamline as well as Michael Hanfland for his assistance.
Funding information
This study was financially supported by the National Science Centre Poland (grant No. DEC-2021/41/B/ST4/02760 awarded to AM). The access to ESRF was financed by the Polish Ministry of Science and Higher Education (decision No. 2021/WK/11).
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