research communications
trans-1-(diphenylphosphanethioyl-κS)-2-(diphenylphosphanoyl)ethene]gold(I) dichloromethane hemisolvate1
of chlorido[aInstitut für Anorganische und Analytische Chemie, Technische Universität Braunschweig, Postfach 3329, D-38023 Braunschweig, Germany
*Correspondence e-mail: p.jones@tu-bs.de
The title compound, [AuCl(C26H22OP2S)]·0.5CH2Cl2, crystallizes with a trans-O—P⋯P—S geometry of the groups either side of the C=C double bond, which prevents any intramolecular contact between the Au and O atoms. The AuI atom exhibits a nearly linear coordination [Cl—Au—S = 177.55 (4)°]. The molecules associate to form broad ribbons parallel to the c axis via two C—H⋯O, one C—H⋯Cl(Au) and one Au⋯Cl interaction.
Keywords: crystal structure; gold; phosphine; chalcogenide.
CCDC reference: 1486017
1. Chemical context
We are interested in phosphine chalcogenide complexes of gold (Taouss & Jones, 2016, and references therein). In general, we have synthesized complexes LAuX, where L is a phosphine chalcogenide and X is chlorine or bromine, and then oxidized these first to gold(III) complexes LAuX3 and further to (LX)+(AuX4)−. The title compound was obtained as an unexpected trans product in minimal yield (a few small crystals) during attempts to recrystallize cis-(Ph2PC=CPPh2S)AuCl (Taouss & Jones, 2014). The oxidation of the second P atom to P=O, presumably by atmospheric oxygen, is not unusual, but we are at a loss to explain the change of configuration at the C=C bond from cis to trans. One possibility, in view of the small amounts involved, is that the cis diphosphine as purchased contained a small amount of trans impurity.
2. Structural commentary
The molecular structure of the title compound is shown in Fig. 1. In the absence of a free phosphorus donor atom, the gold(I) atom is, as expected, coordinated by the softer sulfur donor rather than the oxygen. Bond lengths and angles are essentially as expected (Table 1). The P=S bond is somewhat lengthened compared to non-coordinating phosphine (see Section 4). The torsion angle O1—P1⋯P2—S1 is 174.72 (12)°, which is similar to the values observed for dppe-derived complexes of the type E=PPh2CH2CH2PPh2AuX (E = chalcogen and X = halogen); the dppm analogues E=PPh2CH2PPh2AuX, however, tend to display corresponding torsion angles close to zero, thus promoting short intramolecular Au⋯E contacts (Taouss & Jones, 2014). The Au⋯O distance in the title compound [6.127 (3) Å] is clearly far too long for any significant interaction.
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3. Supramolecular features
The molecules are connected into broad ribbons parallel to the c axis (Fig. 2) by the two shortest C—H⋯O and a C—H⋯Cl(Au) interaction (Table 2), together with an Au1⋯Cl1 contact of 3.6522 (12) Å (symmetry code: −x + 1, −y + 1, −z + 1). The corresponding Au1⋯Au1 contact of 3.9827 (4) Å is probably less significant. The third C—H⋯O contact (not shown in Fig. 2) links the ribbons in the a-axis direction.
4. Database survey
A search of the Cambridge Structural Database (Groom & Allen, 2014; Groom et al., 2016) (Version 5.37, 2015) revealed a mean P=S bond length of 1.954 Å for 485 examples of the non-coordinating moiety Ph2P(=S)C. This increases to 2.025 Å on coordination to an AuCl fragment (7 examples).
Perhaps surprisingly, there seem to be no structures of simple diphosphine dichalcogenides with the chalcogen atom(s) bonded to gold. One relevant publication, however, is that of the cyano-substituted derivative Ph3PAu[S=PPh2—C(CN)—PPh2=S] (Sithole et al., 2016). This has a torsion angle of 70° across the atom sequence S=P⋯P=S because the formally noncoordinating S atom makes a short contact of 2.98 Å to the Au atom.
5. Synthesis and crystallization
Starting from cis-(diphenylphosphanyl)ethene, we generated the monosulfide and then the gold complex cis-(Ph2PC=CPPh2S)AuCl by reaction with (tetrahydrothiophene)AuCl. This compound was successfully crystallized and its structure determined (Taouss & Jones, 2014). On one occasion, however, a few small crystals were obtained that proved not to be the intended compound, but instead the title compound.
6. Refinement
Crystal data, data collection and structure . H atoms were included using a riding model starting from calculated positions, with C—H distances fixed at 0.95 Å. The dichloromethane molecule is disordered over an inversion centre; appropriate restraints were employed to improve stability, but the dimensions of disordered groups should be interpreted with caution.
details are summarized in Table 3Supporting information
CCDC reference: 1486017
https://doi.org/10.1107/S2056989016009816/pj2031sup1.cif
contains datablocks I, global. DOI:Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S2056989016009816/pj2031Isup2.hkl
Data collection: CrysAlis PRO (Agilent, 2010); cell
CrysAlis PRO (Agilent, 2010); data reduction: CrysAlis PRO (Agilent, 2010); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: XP (Siemens, 1994); software used to prepare material for publication: SHELXL97 (Sheldrick, 2008).[AuCl(C26H22OP2S)]·0.5CH2Cl2 | Z = 2 |
Mr = 719.32 | F(000) = 698 |
Triclinic, P1 | Dx = 1.876 Mg m−3 |
a = 8.4458 (3) Å | Mo Kα radiation, λ = 0.71073 Å |
b = 11.4318 (5) Å | Cell parameters from 18482 reflections |
c = 13.8713 (6) Å | θ = 2.1–30.7° |
α = 76.940 (5)° | µ = 6.21 mm−1 |
β = 85.785 (5)° | T = 103 K |
γ = 77.541 (5)° | Plate, pale yellow |
V = 1273.49 (9) Å3 | 0.16 × 0.16 × 0.05 mm |
Oxford Diffraction Xcalibur Eos diffractometer | 5824 independent reflections |
Radiation source: Enhance (Mo) X-ray Source | 4835 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.055 |
Detector resolution: 16.1419 pixels mm-1 | θmax = 27.5°, θmin = 2.1° |
ω–scan | h = −10→10 |
Absorption correction: multi-scan (CrysAlis PRO; Agilent, 2010) | k = −14→14 |
Tmin = 0.644, Tmax = 1.000 | l = −18→18 |
45210 measured reflections |
Refinement on F2 | Primary atom site location: structure-invariant direct methods |
Least-squares matrix: full | Secondary atom site location: difference Fourier map |
R[F2 > 2σ(F2)] = 0.028 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.070 | H-atom parameters constrained |
S = 0.98 | w = 1/[σ2(Fo2) + (0.039P)2] where P = (Fo2 + 2Fc2)/3 |
5824 reflections | (Δ/σ)max = 0.009 |
311 parameters | Δρmax = 1.83 e Å−3 |
19 restraints | Δρmin = −0.86 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. Non-bonded distances: 6.1266 (0.0028) Au1 - O1 3.9827 (0.0004) Au1 - Au1_$2 3.6522 (0.0012) Au1 - Cl1_$2 Operator for generating equivalent atoms: $2 -x+1, -y+1, -z+1 |
Refinement. Refinement of F2 against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F2, conventional R-factors R are based on F, with F set to zero for negative F2. The threshold expression of F2 > 2sigma(F2) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F2 are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. |
x | y | z | Uiso*/Ueq | Occ. (<1) | |
Au1 | 0.52851 (2) | 0.647310 (17) | 0.545348 (14) | 0.01888 (6) | |
Cl1 | 0.27999 (14) | 0.66076 (11) | 0.48600 (9) | 0.0244 (3) | |
O1 | 0.4788 (3) | 0.3560 (2) | 0.9714 (2) | 0.0145 (6) | |
P1 | 0.51137 (12) | 0.34200 (9) | 0.86757 (8) | 0.0095 (2) | |
P2 | 0.72565 (12) | 0.66749 (9) | 0.73564 (8) | 0.0098 (2) | |
S1 | 0.78253 (13) | 0.62695 (10) | 0.60180 (8) | 0.0180 (2) | |
C1 | 0.6026 (5) | 0.4594 (3) | 0.7886 (3) | 0.0107 (8) | |
H1 | 0.6371 | 0.4502 | 0.7235 | 0.013* | |
C2 | 0.6236 (5) | 0.5582 (4) | 0.8175 (3) | 0.0119 (8) | |
H2 | 0.5850 | 0.5714 | 0.8810 | 0.014* | |
C11 | 0.3342 (5) | 0.3399 (3) | 0.8051 (3) | 0.0099 (8) | |
C12 | 0.2241 (5) | 0.2717 (4) | 0.8571 (3) | 0.0170 (9) | |
H12 | 0.2446 | 0.2293 | 0.9236 | 0.020* | |
C13 | 0.0850 (5) | 0.2652 (4) | 0.8124 (3) | 0.0195 (10) | |
H13 | 0.0110 | 0.2186 | 0.8486 | 0.023* | |
C14 | 0.0542 (5) | 0.3263 (4) | 0.7157 (3) | 0.0175 (9) | |
H14 | −0.0405 | 0.3213 | 0.6851 | 0.021* | |
C15 | 0.1620 (5) | 0.3954 (4) | 0.6629 (3) | 0.0168 (9) | |
H15 | 0.1398 | 0.4384 | 0.5967 | 0.020* | |
C16 | 0.3017 (5) | 0.4016 (4) | 0.7066 (3) | 0.0154 (9) | |
H16 | 0.3756 | 0.4477 | 0.6698 | 0.018* | |
C21 | 0.6553 (5) | 0.2024 (3) | 0.8576 (3) | 0.0125 (8) | |
C22 | 0.7163 (5) | 0.1221 (4) | 0.9446 (3) | 0.0194 (10) | |
H22 | 0.6842 | 0.1415 | 1.0072 | 0.023* | |
C23 | 0.8246 (6) | 0.0135 (4) | 0.9384 (4) | 0.0293 (12) | |
H23 | 0.8643 | −0.0428 | 0.9972 | 0.035* | |
C24 | 0.8749 (5) | −0.0132 (4) | 0.8477 (4) | 0.0273 (12) | |
H24 | 0.9498 | −0.0873 | 0.8443 | 0.033* | |
C25 | 0.8169 (5) | 0.0676 (4) | 0.7615 (4) | 0.0251 (11) | |
H25 | 0.8540 | 0.0498 | 0.6990 | 0.030* | |
C26 | 0.7039 (5) | 0.1753 (4) | 0.7661 (3) | 0.0162 (9) | |
H26 | 0.6607 | 0.2293 | 0.7071 | 0.019* | |
C31 | 0.9095 (5) | 0.6644 (3) | 0.7950 (3) | 0.0113 (8) | |
C32 | 1.0489 (5) | 0.6829 (4) | 0.7385 (4) | 0.0195 (10) | |
H32 | 1.0479 | 0.6954 | 0.6684 | 0.023* | |
C33 | 1.1888 (5) | 0.6829 (5) | 0.7846 (4) | 0.0253 (11) | |
H33 | 1.2836 | 0.6963 | 0.7461 | 0.030* | |
C34 | 1.1910 (5) | 0.6638 (4) | 0.8857 (4) | 0.0196 (10) | |
H34 | 1.2875 | 0.6637 | 0.9169 | 0.023* | |
C35 | 1.0536 (5) | 0.6445 (4) | 0.9429 (3) | 0.0199 (10) | |
H35 | 1.0565 | 0.6307 | 1.0129 | 0.024* | |
C36 | 0.9123 (5) | 0.6454 (4) | 0.8982 (3) | 0.0168 (9) | |
H36 | 0.8176 | 0.6332 | 0.9373 | 0.020* | |
C41 | 0.5995 (5) | 0.8183 (3) | 0.7263 (3) | 0.0110 (8) | |
C42 | 0.5999 (6) | 0.9051 (4) | 0.6366 (3) | 0.0192 (10) | |
H42 | 0.6639 | 0.8825 | 0.5819 | 0.023* | |
C43 | 0.5085 (6) | 1.0225 (4) | 0.6270 (3) | 0.0212 (10) | |
H43 | 0.5105 | 1.0808 | 0.5663 | 0.025* | |
C44 | 0.4150 (5) | 1.0543 (4) | 0.7054 (4) | 0.0197 (10) | |
H44 | 0.3495 | 1.1343 | 0.6984 | 0.024* | |
C45 | 0.4149 (6) | 0.9712 (4) | 0.7946 (4) | 0.0286 (12) | |
H45 | 0.3502 | 0.9949 | 0.8487 | 0.034* | |
C46 | 0.5094 (5) | 0.8522 (4) | 0.8062 (3) | 0.0212 (10) | |
H46 | 0.5112 | 0.7958 | 0.8682 | 0.025* | |
C99 | 0.0028 (15) | 0.9195 (12) | 0.5150 (9) | 0.054 (3)* | 0.50 |
H99A | −0.0639 | 0.8733 | 0.5649 | 0.065* | 0.50 |
H99B | 0.0642 | 0.8629 | 0.4745 | 0.065* | 0.50 |
Cl98 | 0.1379 (12) | 0.9738 (9) | 0.5746 (7) | 0.078 (3) | 0.50 |
Cl99 | −0.1245 (10) | 1.0425 (5) | 0.4385 (7) | 0.062 (2) | 0.50 |
U11 | U22 | U33 | U12 | U13 | U23 | |
Au1 | 0.02164 (10) | 0.01867 (10) | 0.01674 (10) | −0.00635 (7) | −0.00190 (6) | −0.00213 (6) |
Cl1 | 0.0235 (6) | 0.0274 (6) | 0.0211 (6) | −0.0072 (5) | −0.0064 (5) | 0.0010 (5) |
O1 | 0.0136 (15) | 0.0147 (15) | 0.0163 (17) | −0.0042 (12) | −0.0004 (13) | −0.0047 (13) |
P1 | 0.0093 (5) | 0.0079 (5) | 0.0118 (5) | −0.0035 (4) | 0.0000 (4) | −0.0013 (4) |
P2 | 0.0080 (5) | 0.0087 (5) | 0.0131 (5) | −0.0032 (4) | 0.0001 (4) | −0.0022 (4) |
S1 | 0.0168 (6) | 0.0182 (6) | 0.0192 (6) | −0.0034 (4) | 0.0001 (5) | −0.0048 (5) |
C1 | 0.0068 (19) | 0.0104 (19) | 0.014 (2) | −0.0013 (15) | −0.0019 (16) | −0.0005 (16) |
C2 | 0.0043 (18) | 0.012 (2) | 0.019 (2) | −0.0013 (15) | 0.0009 (16) | −0.0016 (17) |
C11 | 0.0084 (19) | 0.0082 (19) | 0.014 (2) | −0.0006 (15) | 0.0002 (16) | −0.0062 (16) |
C12 | 0.021 (2) | 0.017 (2) | 0.014 (2) | −0.0090 (18) | −0.0002 (18) | −0.0010 (18) |
C13 | 0.011 (2) | 0.024 (2) | 0.025 (3) | −0.0104 (18) | 0.0016 (19) | −0.004 (2) |
C14 | 0.009 (2) | 0.018 (2) | 0.026 (3) | 0.0004 (17) | −0.0038 (18) | −0.0059 (19) |
C15 | 0.017 (2) | 0.016 (2) | 0.016 (2) | −0.0004 (17) | −0.0038 (18) | 0.0002 (18) |
C16 | 0.013 (2) | 0.015 (2) | 0.018 (2) | −0.0067 (17) | 0.0006 (17) | 0.0012 (17) |
C21 | 0.0093 (19) | 0.0073 (19) | 0.021 (2) | −0.0034 (15) | 0.0005 (17) | −0.0024 (17) |
C22 | 0.019 (2) | 0.018 (2) | 0.019 (2) | −0.0055 (18) | −0.0030 (19) | 0.0028 (18) |
C23 | 0.019 (2) | 0.016 (2) | 0.046 (3) | −0.0037 (19) | −0.003 (2) | 0.007 (2) |
C24 | 0.013 (2) | 0.012 (2) | 0.059 (4) | −0.0010 (18) | −0.002 (2) | −0.012 (2) |
C25 | 0.013 (2) | 0.027 (3) | 0.042 (3) | −0.0050 (19) | 0.003 (2) | −0.021 (2) |
C26 | 0.013 (2) | 0.016 (2) | 0.022 (2) | −0.0047 (17) | −0.0028 (18) | −0.0066 (18) |
C31 | 0.009 (2) | 0.0075 (19) | 0.017 (2) | −0.0012 (15) | −0.0030 (16) | −0.0033 (16) |
C32 | 0.016 (2) | 0.024 (2) | 0.021 (2) | −0.0077 (19) | 0.0019 (19) | −0.008 (2) |
C33 | 0.010 (2) | 0.038 (3) | 0.032 (3) | −0.008 (2) | 0.005 (2) | −0.015 (2) |
C34 | 0.009 (2) | 0.017 (2) | 0.034 (3) | 0.0005 (17) | −0.0092 (19) | −0.007 (2) |
C35 | 0.023 (2) | 0.017 (2) | 0.019 (2) | −0.0057 (19) | −0.0070 (19) | 0.0001 (19) |
C36 | 0.016 (2) | 0.016 (2) | 0.018 (2) | −0.0066 (17) | −0.0020 (18) | 0.0007 (18) |
C41 | 0.011 (2) | 0.0050 (18) | 0.018 (2) | −0.0021 (15) | −0.0047 (17) | −0.0031 (16) |
C42 | 0.025 (2) | 0.021 (2) | 0.010 (2) | 0.0007 (19) | −0.0005 (18) | −0.0054 (18) |
C43 | 0.031 (3) | 0.009 (2) | 0.020 (2) | 0.0035 (19) | −0.012 (2) | 0.0016 (18) |
C44 | 0.016 (2) | 0.010 (2) | 0.031 (3) | 0.0032 (17) | −0.003 (2) | −0.0059 (19) |
C45 | 0.031 (3) | 0.019 (2) | 0.032 (3) | −0.002 (2) | 0.019 (2) | −0.007 (2) |
C46 | 0.024 (2) | 0.015 (2) | 0.021 (2) | −0.0052 (19) | 0.008 (2) | 0.0031 (18) |
Cl98 | 0.065 (4) | 0.134 (6) | 0.061 (3) | −0.061 (4) | 0.032 (2) | −0.046 (4) |
Cl99 | 0.069 (4) | 0.0233 (17) | 0.082 (5) | −0.004 (2) | 0.029 (3) | −0.004 (2) |
Au1—Cl1 | 2.2726 (12) | C24—H24 | 0.9500 |
Au1—S1 | 2.2846 (11) | C25—C26 | 1.396 (6) |
O1—P1 | 1.484 (3) | C25—H25 | 0.9500 |
P1—C11 | 1.791 (4) | C26—H26 | 0.9500 |
P1—C1 | 1.803 (4) | C31—C32 | 1.394 (6) |
P1—C21 | 1.811 (4) | C31—C36 | 1.399 (6) |
P2—C31 | 1.801 (4) | C32—C33 | 1.385 (6) |
P2—C41 | 1.803 (4) | C32—H32 | 0.9500 |
P2—C2 | 1.809 (4) | C33—C34 | 1.371 (7) |
P2—S1 | 2.0135 (16) | C33—H33 | 0.9500 |
C1—C2 | 1.330 (6) | C34—C35 | 1.386 (6) |
C1—H1 | 0.9500 | C34—H34 | 0.9500 |
C2—H2 | 0.9500 | C35—C36 | 1.382 (6) |
C11—C12 | 1.397 (6) | C35—H35 | 0.9500 |
C11—C16 | 1.406 (6) | C36—H36 | 0.9500 |
C12—C13 | 1.391 (6) | C41—C46 | 1.379 (6) |
C12—H12 | 0.9500 | C41—C42 | 1.406 (6) |
C13—C14 | 1.380 (6) | C42—C43 | 1.379 (6) |
C13—H13 | 0.9500 | C42—H42 | 0.9500 |
C14—C15 | 1.392 (6) | C43—C44 | 1.367 (6) |
C14—H14 | 0.9500 | C43—H43 | 0.9500 |
C15—C16 | 1.387 (6) | C44—C45 | 1.379 (7) |
C15—H15 | 0.9500 | C44—H44 | 0.9500 |
C16—H16 | 0.9500 | C45—C46 | 1.402 (6) |
C21—C26 | 1.387 (6) | C45—H45 | 0.9500 |
C21—C22 | 1.397 (6) | C46—H46 | 0.9500 |
C22—C23 | 1.391 (6) | C99—Cl98 | 1.747 (12) |
C22—H22 | 0.9500 | C99—Cl99 | 1.760 (11) |
C23—C24 | 1.376 (8) | C99—H99A | 0.9900 |
C23—H23 | 0.9500 | C99—H99B | 0.9900 |
C24—C25 | 1.384 (7) | ||
Cl1—Au1—S1 | 177.55 (4) | C25—C24—H24 | 119.9 |
O1—P1—C11 | 113.74 (17) | C24—C25—C26 | 120.2 (5) |
O1—P1—C1 | 114.90 (18) | C24—C25—H25 | 119.9 |
C11—P1—C1 | 105.43 (19) | C26—C25—H25 | 119.9 |
O1—P1—C21 | 112.88 (18) | C21—C26—C25 | 119.3 (4) |
C11—P1—C21 | 106.13 (18) | C21—C26—H26 | 120.3 |
C1—P1—C21 | 102.73 (18) | C25—C26—H26 | 120.3 |
C31—P2—C41 | 107.84 (18) | C32—C31—C36 | 119.7 (4) |
C31—P2—C2 | 106.69 (19) | C32—C31—P2 | 120.2 (3) |
C41—P2—C2 | 108.17 (18) | C36—C31—P2 | 120.1 (3) |
C31—P2—S1 | 109.00 (14) | C33—C32—C31 | 119.9 (4) |
C41—P2—S1 | 111.91 (15) | C33—C32—H32 | 120.1 |
C2—P2—S1 | 112.98 (15) | C31—C32—H32 | 120.1 |
P2—S1—Au1 | 100.06 (5) | C34—C33—C32 | 120.2 (4) |
C2—C1—P1 | 122.9 (3) | C34—C33—H33 | 119.9 |
C2—C1—H1 | 118.5 | C32—C33—H33 | 119.9 |
P1—C1—H1 | 118.5 | C33—C34—C35 | 120.5 (4) |
C1—C2—P2 | 120.0 (3) | C33—C34—H34 | 119.7 |
C1—C2—H2 | 120.0 | C35—C34—H34 | 119.7 |
P2—C2—H2 | 120.0 | C36—C35—C34 | 120.2 (4) |
C12—C11—C16 | 118.6 (4) | C36—C35—H35 | 119.9 |
C12—C11—P1 | 117.9 (3) | C34—C35—H35 | 119.9 |
C16—C11—P1 | 123.5 (3) | C35—C36—C31 | 119.6 (4) |
C13—C12—C11 | 120.8 (4) | C35—C36—H36 | 120.2 |
C13—C12—H12 | 119.6 | C31—C36—H36 | 120.2 |
C11—C12—H12 | 119.6 | C46—C41—C42 | 119.4 (4) |
C14—C13—C12 | 120.1 (4) | C46—C41—P2 | 121.7 (3) |
C14—C13—H13 | 119.9 | C42—C41—P2 | 118.9 (3) |
C12—C13—H13 | 119.9 | C43—C42—C41 | 120.9 (4) |
C13—C14—C15 | 119.9 (4) | C43—C42—H42 | 119.6 |
C13—C14—H14 | 120.0 | C41—C42—H42 | 119.6 |
C15—C14—H14 | 120.0 | C44—C43—C42 | 119.5 (4) |
C16—C15—C14 | 120.3 (4) | C44—C43—H43 | 120.3 |
C16—C15—H15 | 119.9 | C42—C43—H43 | 120.3 |
C14—C15—H15 | 119.9 | C43—C44—C45 | 120.6 (4) |
C15—C16—C11 | 120.3 (4) | C43—C44—H44 | 119.7 |
C15—C16—H16 | 119.9 | C45—C44—H44 | 119.7 |
C11—C16—H16 | 119.9 | C44—C45—C46 | 120.7 (4) |
C26—C21—C22 | 120.5 (4) | C44—C45—H45 | 119.7 |
C26—C21—P1 | 121.1 (3) | C46—C45—H45 | 119.7 |
C22—C21—P1 | 118.4 (3) | C41—C46—C45 | 119.0 (4) |
C23—C22—C21 | 119.1 (4) | C41—C46—H46 | 120.5 |
C23—C22—H22 | 120.5 | C45—C46—H46 | 120.5 |
C21—C22—H22 | 120.5 | Cl98—C99—Cl99 | 110.3 (9) |
C24—C23—C22 | 120.6 (5) | Cl98—C99—H99A | 109.6 |
C24—C23—H23 | 119.7 | Cl99—C99—H99A | 109.6 |
C22—C23—H23 | 119.7 | Cl98—C99—H99B | 109.6 |
C23—C24—C25 | 120.2 (4) | Cl99—C99—H99B | 109.6 |
C23—C24—H24 | 119.9 | H99A—C99—H99B | 108.1 |
C31—P2—S1—Au1 | −177.51 (14) | C22—C23—C24—C25 | −0.6 (7) |
C41—P2—S1—Au1 | −58.32 (15) | C23—C24—C25—C26 | −1.6 (7) |
C2—P2—S1—Au1 | 64.07 (15) | C22—C21—C26—C25 | −1.1 (6) |
Cl1—Au1—S1—P2 | −143.9 (10) | P1—C21—C26—C25 | 179.1 (3) |
O1—P1—C1—C2 | −6.9 (4) | C24—C25—C26—C21 | 2.4 (6) |
C11—P1—C1—C2 | 119.2 (4) | C41—P2—C31—C32 | −97.6 (4) |
C21—P1—C1—C2 | −129.9 (4) | C2—P2—C31—C32 | 146.4 (3) |
P1—C1—C2—P2 | 176.8 (2) | S1—P2—C31—C32 | 24.1 (4) |
C31—P2—C2—C1 | −115.7 (3) | C41—P2—C31—C36 | 81.3 (4) |
C41—P2—C2—C1 | 128.5 (3) | C2—P2—C31—C36 | −34.7 (4) |
S1—P2—C2—C1 | 4.1 (4) | S1—P2—C31—C36 | −157.0 (3) |
O1—P1—C11—C12 | −42.7 (4) | C36—C31—C32—C33 | −0.3 (6) |
C1—P1—C11—C12 | −169.4 (3) | P2—C31—C32—C33 | 178.6 (3) |
C21—P1—C11—C12 | 82.0 (3) | C31—C32—C33—C34 | 0.6 (7) |
O1—P1—C11—C16 | 138.3 (3) | C32—C33—C34—C35 | −0.2 (7) |
C1—P1—C11—C16 | 11.5 (4) | C33—C34—C35—C36 | −0.5 (7) |
C21—P1—C11—C16 | −97.0 (4) | C34—C35—C36—C31 | 0.7 (6) |
C16—C11—C12—C13 | −0.2 (6) | C32—C31—C36—C35 | −0.4 (6) |
P1—C11—C12—C13 | −179.3 (3) | P2—C31—C36—C35 | −179.3 (3) |
C11—C12—C13—C14 | 0.1 (7) | C31—P2—C41—C46 | −78.6 (4) |
C12—C13—C14—C15 | −0.5 (7) | C2—P2—C41—C46 | 36.4 (4) |
C13—C14—C15—C16 | 1.0 (6) | S1—P2—C41—C46 | 161.5 (3) |
C14—C15—C16—C11 | −1.1 (6) | C31—P2—C41—C42 | 98.0 (4) |
C12—C11—C16—C15 | 0.7 (6) | C2—P2—C41—C42 | −146.9 (3) |
P1—C11—C16—C15 | 179.7 (3) | S1—P2—C41—C42 | −21.8 (4) |
O1—P1—C21—C26 | −178.3 (3) | C46—C41—C42—C43 | −1.5 (7) |
C11—P1—C21—C26 | 56.5 (4) | P2—C41—C42—C43 | −178.3 (4) |
C1—P1—C21—C26 | −54.0 (4) | C41—C42—C43—C44 | −0.7 (7) |
O1—P1—C21—C22 | 1.9 (4) | C42—C43—C44—C45 | 1.8 (7) |
C11—P1—C21—C22 | −123.4 (3) | C43—C44—C45—C46 | −0.7 (8) |
C1—P1—C21—C22 | 126.2 (3) | C42—C41—C46—C45 | 2.7 (7) |
C26—C21—C22—C23 | −1.0 (6) | P2—C41—C46—C45 | 179.3 (4) |
P1—C21—C22—C23 | 178.9 (3) | C44—C45—C46—C41 | −1.6 (8) |
C21—C22—C23—C24 | 1.8 (7) |
D—H···A | D—H | H···A | D···A | D—H···A |
C2—H2···O1i | 0.95 | 2.36 | 3.294 (5) | 166 |
C46—H46···O1i | 0.95 | 2.49 | 3.438 (5) | 179 |
C26—H26···Cl1ii | 0.95 | 2.75 | 3.583 (5) | 147 |
C34—H34···O1iii | 0.95 | 2.54 | 3.478 (5) | 170 |
Symmetry codes: (i) −x+1, −y+1, −z+2; (ii) −x+1, −y+1, −z+1; (iii) −x+2, −y+1, −z+2. |
Footnotes
1Phosphane chalcogenides and their metal complexes, Part V. For Part IV, see Taouss & Jones (2016).
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