research communications
Intermolecular hydrogen bonding in isostructural pincer complexes [OH-(t-BuPOCOPt-Bu)MCl] (M = Pd and Pt)
aLeibniz-Institut für Katalyse e. V. an der Universität Rostock, Albert-Einstein-Str. 29a, 18059 Rostock, Germany
*Correspondence e-mail: torsten.beweries@catalysis.de
In the tert-butylphosphanyl)oxy]-4-hydroxyphenyl}chloridopalladium(II), [Pd(C22H39O3P2)Cl], 1, and {2,6-bis[(di-tert-butylphosphanyl)oxy]-4-hydroxyphenyl}chloridoplatinum(II), [Pt(C22H39O3P2)Cl], 2, the metal centres are coordinated in a distorted square-planar fashion by the POCOP pincer fragment and the chloride ligand. Both complexes form strong hydrogen-bonded chain structures through an interaction of the OH group in the 4-position of the aromatic POCOP backbone with the halide ligand.
of the isostructural title compounds, namely {2,6-bis[(di-Keywords: pincer complexes; palladium; platinum; hydrogen bonding; crystal structure.
1. Chemical context
Since their discovery by Shaw and van Koten in the 1970s (Moulton & Shaw, 1976; van Koten et al., 1978), pincer complexes have received considerable attention in organometallic chemistry and because of their wide applicability for a broad range of stoichiometric and catalytic bond-activation reactions (e.g. Szabo & Wendt, 2014; Valdés et al., 2018). Modification of the pincer scaffold allows for fine-tuning of the steric and electronic properties that directly influence the reactivity (Peris & Crabtree, 2018). As a consequence, a plethora of transition metal complexes that possess neutral and anionic tridentate pincer ligands with many different combinations of donor atoms have been described. Substitution of the pincer backbone with suitable polar groups provides an excellent opportunity for the introduction of anchoring sites that can be attached covalently to a heterogeneous support (Rimoldi et al., 2016). In this context, hydroxylation of the aromatic ring of a POCOP ligand is a straightforward approach and the ligand precursor phloroglucinol is a readily available compound that can be converted into the corresponding ligand using standard methodologies (Göttker-Schnetmann et al., 2004; Garcia-Eleno et al., 2015). This polar functionality can engage in non-covalent interactions with ubiquitous metal-halide fragments. An example for this phenomenon that includes halide–halide interactions was reported recently by Whitwood, Brammer and Perutz, who studied intermolecular halogen bonding of a series of nickel(II) fluoride complexes (Thangavadivale et al., 2018). For a recent review article on the application of pincer complexes, see Valdés et al. (2018).
2. Structural commentary
Complexes 1 and 2 are isomorphous and both crystallize in the monoclinic P21/n with one molecule in the The molecular structures (Fig. 1) show the metal(II) centres in a distorted square-planar coordination environment. The distortion is evidenced by the P—M—P angles that strongly deviate from 180° [1: 159.768 (12), 2: 160.676 (17)°]. The M—Cl [1: 2.3871 (4), 2: 2.3907 (5) Å] and M—P bonds [1: 2.2880 (3), 2.2918 (3); 2: 2.2781 (5), 2.2796 (5) Å] are in the expected ranges and are in line with values found in previous examples for Pd and Pt PCP pincer complexes (e.g. Bolliger et al., 2007; Joksch et al., 2017, 2018). As can be seen from the structural data, variation of the metal centre does not affect the structural features of the pincer complex. Complexes 1 and 2 are isostructural to the dichloroethane solvate of a similar nickel complex (Garcia-Eleno et al., 2015).
3. Supramolecular features
In both complexes, the OH group in the 4-position of the POCOP ligand shows pronounced intermolecular hydrogen bonding to the chloride ligand (Tables 1 and 2), thus resulting in the formation of infinite chain structures along [101] (Figs. 2 and 3). A dihedral angle of 31.38 (6)° in 1 and 31.74 (9)° in 2 between the planes of the aryl rings of neighbouring pincer complexes involved in hydrogen bonding was observed.
4. Database survey
A search of the Cambridge Structural Database (CSD, Version 5.40, May 2019 update; Groom et al., 2016) for Pd and Pt POCOP halide complexes with aromatic ligand backbones resulted in 58 hits. Similar Pd and Pt pincer complexes without the OH group in the 4-position have been reported by our group (Joksch et al., 2017, 2018). Related complexes have been described, e.g. by Frech and co-workers (Bolliger et al., 2007), Jensen and co-workers (Morales-Morales et al., 2000; Wang et al., 2006), Wendt and co-workers (Johnson et al., 2013) or Milstein and co-workers (Vuzman et al., 2007).
5. Synthesis and crystallization
Complex 1: Pd(MeCN)Cl2 (261 mg, 1.01 mmol) and the ligand precursor 3,5-bis[(di-tert-butylphosphanyl)oxy]phenol (501 mg, 1.21 mmol) were dissolved in 20 mL of toluene and the mixture was heated at 388 K for two days, resulting in a yellow solution. Upon slow cooling, complex 1 precipitated as a pale-yellow solid, which was isolated by filtration and washed with cold toluene. Colourless crystals suitable for X-ray analysis were obtained from a saturated toluene solution at 195 K, yield: 216 mg (39%). 1H NMR (300.13 MHz, 295 K, toluene-d8): 5.98 (s, 2H, m-CH), 3.92 (br s, 1H, OH), 1.34 ppm (vt, 36H, t-Bu). 13C NMR (75.48 MHz, 295 K, toluene-d8, assigned by 1H-13C-HMBC): 167.4 [C-OP(t-Bu)2], 157.2 (C—OH), 121.4 (Pd—C), 94.4 (m—CH), 39.5 [C(CH3)3], 27.6 [C(CH3)3]. 31P NMR (121.50 MHz, 295 K, toluene-d8): 193.5 ppm. Analysis calculated for C22H39ClO3P2Pd: C, 47.58; H, 7.08. Found: C, 47.43; H, 7.13. MS (CI positive, iso-butane): m/z 554 [M]+.
Complex 2: Pt(cod)Cl2 (147 mg, 0.39 mmol) and the ligand precursor 3,5-bis[(di-tert-butylphosphanyl)oxy]phenol (195 mg, 1.47 mmol) were dissolved in 15 mL of toluene and the mixture was heated at 388 K for 16 h, resulting in a colourless solution. After cooling to room temperature, the solvent was removed in vacuum and the residue was washed with n-hexane to yield complex 2 as a colourless solid. Crystals suitable for X-ray analysis were obtained by slow cooling of a hot saturated toluene solution to room temperature. Yield: 214 mg (85%). 1H NMR (400.13 MHz, 297 K, toluene-d8): 6.03 (t, J = 7.53 Hz, 2H, m-CH), 4.10 (br s, 1H, OH), 1.33 (vt, 36H, t-Bu). 13C NMR (100.63 MHz, 297 K, toluene-d8): 165.8 [C—OP(t-Bu)2], 156.5 (C—OH), 112.5 (Pt—C), 94.2 (m—CH), 40.6 [C(CH3)3], 27.6 [C(CH3)3]. 31P NMR (161.98 MHz, 297 K, toluene-d8): 178.1. Analysis calculated for C22H39ClO3P2Pt: C, 41.03; H, 6.10. Found: C, 41.17; H, 5.99. MS (CI positive, iso-butane): m/z 644 [M]+, 608 [M - Cl]+.
6. Refinement
Crystal data, data collection and structure . Hydrogen atoms attached to oxygen could be found in a difference-Fourier map and were refined freely. All other H atoms were placed in idealized positions with d(C—H) = 0.95 Å (CH), 0.98 Å (CH3) and refined using a riding model with Uiso(H) fixed at 1.2Ueq(C) for CH and 1.5Ueq(C) for CH3. A rotating model was used for the methyl groups.
details are summarized in Table 3Supporting information
https://doi.org/10.1107/S2056989019008491/rz5258sup1.cif
contains datablocks 1, 2, New_Global_Publ_Block. DOI:Structure factors: contains datablock 1. DOI: https://doi.org/10.1107/S2056989019008491/rz52581sup2.hkl
Structure factors: contains datablock 2. DOI: https://doi.org/10.1107/S2056989019008491/rz52582sup3.hkl
For both structures, data collection: APEX2 (Bruker, 2014); cell
SAINT (Bruker, 2014); data reduction: SAINT (Bruker, 2014); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL2014/7 (Sheldrick, 2015); molecular graphics: XP in SHELXTL (Sheldrick, 2008); software used to prepare material for publication: publCIF (Westrip, 2010).[Pd(C22H39O3P2)Cl] | F(000) = 1152 |
Mr = 555.32 | Dx = 1.389 Mg m−3 |
Monoclinic, P21/n | Mo Kα radiation, λ = 0.71073 Å |
a = 9.7678 (5) Å | Cell parameters from 9082 reflections |
b = 20.1652 (10) Å | θ = 2.4–30.5° |
c = 13.9656 (7) Å | µ = 0.94 mm−1 |
β = 105.1743 (8)° | T = 150 K |
V = 2654.9 (2) Å3 | Prism, colourless |
Z = 4 | 0.37 × 0.36 × 0.36 mm |
Bruker APEXII CCD diffractometer | 6411 independent reflections |
Radiation source: fine-focus sealed tube | 6166 reflections with I > 2σ(I) |
Detector resolution: 8.3333 pixels mm-1 | Rint = 0.018 |
φ and ω scans | θmax = 28.0°, θmin = 1.8° |
Absorption correction: multi-scan (SADABS; Bruker, 2014) | h = −12→12 |
Tmin = 0.68, Tmax = 0.73 | k = −26→26 |
57317 measured reflections | l = −18→18 |
Refinement on F2 | 0 restraints |
Least-squares matrix: full | Hydrogen site location: mixed |
R[F2 > 2σ(F2)] = 0.018 | H atoms treated by a mixture of independent and constrained refinement |
wR(F2) = 0.046 | w = 1/[σ2(Fo2) + (0.0197P)2 + 1.5724P] where P = (Fo2 + 2Fc2)/3 |
S = 1.08 | (Δ/σ)max < 0.001 |
6411 reflections | Δρmax = 0.49 e Å−3 |
278 parameters | Δρmin = −0.45 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 | ||
C1 | 0.21967 (12) | 0.29775 (6) | −0.06646 (9) | 0.0158 (2) | |
C2 | 0.32101 (13) | 0.27370 (6) | −0.11161 (9) | 0.0157 (2) | |
C3 | 0.38045 (13) | 0.31168 (6) | −0.17336 (9) | 0.0168 (2) | |
H3 | 0.4473 | 0.2932 | −0.2044 | 0.020* | |
C4 | 0.33893 (13) | 0.37773 (6) | −0.18831 (9) | 0.0174 (2) | |
C5 | 0.23941 (13) | 0.40494 (6) | −0.14407 (9) | 0.0187 (2) | |
H5 | 0.2125 | 0.4502 | −0.1537 | 0.022* | |
C6 | 0.18083 (12) | 0.36393 (6) | −0.08548 (9) | 0.0165 (2) | |
C7 | 0.20805 (14) | 0.09712 (7) | −0.10482 (10) | 0.0232 (3) | |
C8 | 0.11293 (18) | 0.13104 (9) | −0.19722 (12) | 0.0396 (4) | |
H8A | 0.1715 | 0.1584 | −0.2289 | 0.059* | |
H8B | 0.0431 | 0.1591 | −0.1775 | 0.059* | |
H8C | 0.0636 | 0.0972 | −0.2440 | 0.059* | |
C9 | 0.11526 (19) | 0.05436 (9) | −0.05637 (14) | 0.0406 (4) | |
H9A | 0.0636 | 0.0218 | −0.1044 | 0.061* | |
H9B | 0.0474 | 0.0827 | −0.0348 | 0.061* | |
H9C | 0.1754 | 0.0313 | 0.0012 | 0.061* | |
C10 | 0.31748 (17) | 0.05426 (7) | −0.13615 (13) | 0.0325 (3) | |
H10A | 0.3734 | 0.0297 | −0.0786 | 0.049* | |
H10B | 0.3805 | 0.0826 | −0.1625 | 0.049* | |
H10C | 0.2689 | 0.0229 | −0.1875 | 0.049* | |
C11 | 0.44379 (14) | 0.14362 (7) | 0.08081 (10) | 0.0227 (3) | |
C12 | 0.40374 (18) | 0.08715 (8) | 0.14186 (12) | 0.0351 (3) | |
H12A | 0.4794 | 0.0811 | 0.2030 | 0.053* | |
H12B | 0.3911 | 0.0461 | 0.1030 | 0.053* | |
H12C | 0.3151 | 0.0982 | 0.1586 | 0.053* | |
C13 | 0.57549 (15) | 0.12576 (8) | 0.04517 (12) | 0.0315 (3) | |
H13A | 0.6557 | 0.1171 | 0.1027 | 0.047* | |
H13B | 0.5989 | 0.1628 | 0.0068 | 0.047* | |
H13C | 0.5557 | 0.0861 | 0.0033 | 0.047* | |
C14 | 0.47797 (16) | 0.20604 (8) | 0.14625 (11) | 0.0300 (3) | |
H14A | 0.3977 | 0.2163 | 0.1736 | 0.045* | |
H14B | 0.4951 | 0.2435 | 0.1061 | 0.045* | |
H14C | 0.5629 | 0.1980 | 0.2006 | 0.045* | |
C15 | −0.16995 (14) | 0.34028 (7) | −0.02248 (11) | 0.0246 (3) | |
C16 | −0.22961 (16) | 0.40832 (8) | −0.06139 (13) | 0.0354 (3) | |
H16A | −0.3313 | 0.4043 | −0.0934 | 0.053* | |
H16B | −0.1806 | 0.4245 | −0.1097 | 0.053* | |
H16C | −0.2150 | 0.4396 | −0.0060 | 0.053* | |
C17 | −0.24584 (17) | 0.31354 (9) | 0.05250 (14) | 0.0405 (4) | |
H17A | −0.3467 | 0.3073 | 0.0197 | 0.061* | |
H17B | −0.2356 | 0.3453 | 0.1071 | 0.061* | |
H17C | −0.2038 | 0.2710 | 0.0787 | 0.061* | |
C18 | −0.19456 (18) | 0.29240 (10) | −0.11087 (14) | 0.0428 (4) | |
H18A | −0.1665 | 0.2475 | −0.0867 | 0.064* | |
H18B | −0.1376 | 0.3065 | −0.1555 | 0.064* | |
H18C | −0.2952 | 0.2926 | −0.1468 | 0.064* | |
C19 | 0.08541 (15) | 0.38393 (7) | 0.15092 (10) | 0.0228 (3) | |
C20 | 0.24411 (17) | 0.39741 (9) | 0.16379 (13) | 0.0383 (4) | |
H20A | 0.2846 | 0.4180 | 0.2286 | 0.057* | |
H20B | 0.2558 | 0.4273 | 0.1112 | 0.057* | |
H20C | 0.2931 | 0.3555 | 0.1598 | 0.057* | |
C21 | 0.00919 (17) | 0.44979 (7) | 0.15343 (11) | 0.0291 (3) | |
H21A | −0.0898 | 0.4413 | 0.1529 | 0.044* | |
H21B | 0.0122 | 0.4762 | 0.0952 | 0.044* | |
H21C | 0.0562 | 0.4741 | 0.2138 | 0.044* | |
C22 | 0.0681 (2) | 0.33840 (8) | 0.23496 (11) | 0.0363 (4) | |
H22A | 0.1114 | 0.3593 | 0.2991 | 0.054* | |
H22B | 0.1148 | 0.2959 | 0.2309 | 0.054* | |
H22C | −0.0330 | 0.3309 | 0.2286 | 0.054* | |
Cl1 | 0.03724 (5) | 0.17138 (2) | 0.12263 (3) | 0.03930 (10) | |
O1 | 0.36634 (9) | 0.20853 (4) | −0.09447 (7) | 0.01852 (17) | |
O2 | 0.39346 (11) | 0.41889 (5) | −0.24683 (8) | 0.0243 (2) | |
O3 | 0.07741 (9) | 0.39017 (4) | −0.04466 (7) | 0.01986 (18) | |
P1 | 0.28824 (3) | 0.16660 (2) | −0.02188 (2) | 0.01575 (6) | |
P2 | 0.02457 (3) | 0.33937 (2) | 0.03141 (2) | 0.01631 (6) | |
Pd1 | 0.13707 (2) | 0.24105 (2) | 0.02025 (2) | 0.01624 (3) | |
H2 | 0.435 (2) | 0.3971 (10) | −0.2769 (15) | 0.039 (5)* |
U11 | U22 | U33 | U12 | U13 | U23 | |
C1 | 0.0166 (5) | 0.0163 (5) | 0.0162 (5) | 0.0017 (4) | 0.0072 (4) | 0.0020 (4) |
C2 | 0.0173 (5) | 0.0139 (5) | 0.0161 (5) | 0.0029 (4) | 0.0049 (4) | 0.0016 (4) |
C3 | 0.0168 (5) | 0.0179 (5) | 0.0179 (5) | 0.0027 (4) | 0.0082 (4) | 0.0014 (4) |
C4 | 0.0193 (5) | 0.0170 (5) | 0.0179 (5) | 0.0004 (4) | 0.0082 (4) | 0.0031 (4) |
C5 | 0.0218 (6) | 0.0143 (5) | 0.0220 (6) | 0.0030 (4) | 0.0094 (5) | 0.0028 (4) |
C6 | 0.0160 (5) | 0.0177 (5) | 0.0175 (5) | 0.0028 (4) | 0.0072 (4) | −0.0006 (4) |
C7 | 0.0253 (6) | 0.0210 (6) | 0.0261 (6) | −0.0039 (5) | 0.0113 (5) | −0.0061 (5) |
C8 | 0.0368 (8) | 0.0459 (9) | 0.0296 (8) | 0.0011 (7) | −0.0031 (6) | −0.0098 (7) |
C9 | 0.0457 (9) | 0.0371 (9) | 0.0478 (10) | −0.0214 (7) | 0.0282 (8) | −0.0155 (7) |
C10 | 0.0361 (8) | 0.0236 (7) | 0.0432 (9) | −0.0029 (6) | 0.0199 (7) | −0.0129 (6) |
C11 | 0.0245 (6) | 0.0212 (6) | 0.0213 (6) | 0.0024 (5) | 0.0041 (5) | 0.0058 (5) |
C12 | 0.0422 (9) | 0.0301 (8) | 0.0312 (8) | 0.0009 (6) | 0.0065 (7) | 0.0154 (6) |
C13 | 0.0246 (7) | 0.0330 (8) | 0.0351 (8) | 0.0087 (6) | 0.0047 (6) | 0.0049 (6) |
C14 | 0.0317 (7) | 0.0327 (7) | 0.0228 (7) | −0.0025 (6) | 0.0022 (6) | −0.0009 (6) |
C15 | 0.0180 (6) | 0.0280 (7) | 0.0287 (7) | −0.0009 (5) | 0.0078 (5) | −0.0009 (5) |
C16 | 0.0223 (7) | 0.0364 (8) | 0.0455 (9) | 0.0061 (6) | 0.0051 (6) | 0.0065 (7) |
C17 | 0.0279 (8) | 0.0462 (9) | 0.0537 (10) | −0.0051 (7) | 0.0218 (7) | 0.0081 (8) |
C18 | 0.0291 (8) | 0.0500 (10) | 0.0424 (9) | 0.0002 (7) | −0.0030 (7) | −0.0173 (8) |
C19 | 0.0275 (6) | 0.0208 (6) | 0.0204 (6) | 0.0026 (5) | 0.0069 (5) | −0.0027 (5) |
C20 | 0.0272 (7) | 0.0430 (9) | 0.0407 (9) | −0.0008 (7) | 0.0015 (6) | −0.0151 (7) |
C21 | 0.0411 (8) | 0.0198 (6) | 0.0289 (7) | 0.0050 (6) | 0.0133 (6) | −0.0036 (5) |
C22 | 0.0612 (11) | 0.0277 (7) | 0.0209 (7) | 0.0105 (7) | 0.0125 (7) | 0.0021 (6) |
Cl1 | 0.0649 (3) | 0.02367 (16) | 0.0452 (2) | −0.00300 (16) | 0.0427 (2) | 0.00352 (15) |
O1 | 0.0233 (4) | 0.0142 (4) | 0.0219 (4) | 0.0054 (3) | 0.0127 (4) | 0.0047 (3) |
O2 | 0.0318 (5) | 0.0179 (4) | 0.0308 (5) | 0.0036 (4) | 0.0215 (4) | 0.0065 (4) |
O3 | 0.0224 (4) | 0.0166 (4) | 0.0256 (4) | 0.0048 (3) | 0.0152 (4) | 0.0032 (3) |
P1 | 0.01950 (14) | 0.01287 (13) | 0.01668 (14) | 0.00141 (11) | 0.00791 (11) | 0.00152 (10) |
P2 | 0.01767 (14) | 0.01587 (14) | 0.01803 (14) | 0.00131 (11) | 0.00938 (11) | −0.00007 (11) |
Pd1 | 0.02072 (5) | 0.01407 (5) | 0.01727 (5) | 0.00096 (3) | 0.01092 (4) | 0.00110 (3) |
C1—C2 | 1.3926 (16) | C14—H14A | 0.9800 |
C1—C6 | 1.3937 (16) | C14—H14B | 0.9800 |
C1—Pd1 | 1.9841 (12) | C14—H14C | 0.9800 |
C2—O1 | 1.3873 (14) | C15—C17 | 1.531 (2) |
C2—C3 | 1.3891 (16) | C15—C16 | 1.533 (2) |
C3—C4 | 1.3920 (17) | C15—C18 | 1.536 (2) |
C3—H3 | 0.9500 | C15—P2 | 1.8516 (14) |
C4—O2 | 1.3670 (14) | C16—H16A | 0.9800 |
C4—C5 | 1.3936 (17) | C16—H16B | 0.9800 |
C5—C6 | 1.3878 (17) | C16—H16C | 0.9800 |
C5—H5 | 0.9500 | C17—H17A | 0.9800 |
C6—O3 | 1.3881 (14) | C17—H17B | 0.9800 |
C7—C10 | 1.5250 (19) | C17—H17C | 0.9800 |
C7—C9 | 1.531 (2) | C18—H18A | 0.9800 |
C7—C8 | 1.539 (2) | C18—H18B | 0.9800 |
C7—P1 | 1.8557 (13) | C18—H18C | 0.9800 |
C8—H8A | 0.9800 | C19—C21 | 1.5274 (18) |
C8—H8B | 0.9800 | C19—C22 | 1.534 (2) |
C8—H8C | 0.9800 | C19—C20 | 1.537 (2) |
C9—H9A | 0.9800 | C19—P2 | 1.8512 (13) |
C9—H9B | 0.9800 | C20—H20A | 0.9800 |
C9—H9C | 0.9800 | C20—H20B | 0.9800 |
C10—H10A | 0.9800 | C20—H20C | 0.9800 |
C10—H10B | 0.9800 | C21—H21A | 0.9800 |
C10—H10C | 0.9800 | C21—H21B | 0.9800 |
C11—C12 | 1.5334 (19) | C21—H21C | 0.9800 |
C11—C13 | 1.539 (2) | C22—H22A | 0.9800 |
C11—C14 | 1.540 (2) | C22—H22B | 0.9800 |
C11—P1 | 1.8545 (13) | C22—H22C | 0.9800 |
C12—H12A | 0.9800 | Cl1—Pd1 | 2.3871 (4) |
C12—H12B | 0.9800 | O1—P1 | 1.6521 (9) |
C12—H12C | 0.9800 | O2—H2 | 0.79 (2) |
C13—H13A | 0.9800 | O3—P2 | 1.6527 (9) |
C13—H13B | 0.9800 | P1—Pd1 | 2.2880 (3) |
C13—H13C | 0.9800 | P2—Pd1 | 2.2918 (3) |
C2—C1—C6 | 115.95 (11) | C16—C15—C18 | 108.22 (13) |
C2—C1—Pd1 | 121.76 (9) | C17—C15—P2 | 110.34 (11) |
C6—C1—Pd1 | 122.29 (9) | C16—C15—P2 | 114.03 (10) |
O1—C2—C3 | 117.58 (10) | C18—C15—P2 | 104.39 (10) |
O1—C2—C1 | 118.97 (10) | C15—C16—H16A | 109.5 |
C3—C2—C1 | 123.44 (11) | C15—C16—H16B | 109.5 |
C2—C3—C4 | 117.90 (11) | H16A—C16—H16B | 109.5 |
C2—C3—H3 | 121.0 | C15—C16—H16C | 109.5 |
C4—C3—H3 | 121.0 | H16A—C16—H16C | 109.5 |
O2—C4—C3 | 121.80 (11) | H16B—C16—H16C | 109.5 |
O2—C4—C5 | 116.88 (11) | C15—C17—H17A | 109.5 |
C3—C4—C5 | 121.33 (11) | C15—C17—H17B | 109.5 |
C6—C5—C4 | 118.03 (11) | H17A—C17—H17B | 109.5 |
C6—C5—H5 | 121.0 | C15—C17—H17C | 109.5 |
C4—C5—H5 | 121.0 | H17A—C17—H17C | 109.5 |
C5—C6—O3 | 118.14 (11) | H17B—C17—H17C | 109.5 |
C5—C6—C1 | 123.31 (11) | C15—C18—H18A | 109.5 |
O3—C6—C1 | 118.54 (10) | C15—C18—H18B | 109.5 |
C10—C7—C9 | 110.38 (12) | H18A—C18—H18B | 109.5 |
C10—C7—C8 | 109.03 (13) | C15—C18—H18C | 109.5 |
C9—C7—C8 | 108.88 (13) | H18A—C18—H18C | 109.5 |
C10—C7—P1 | 113.20 (10) | H18B—C18—H18C | 109.5 |
C9—C7—P1 | 110.57 (10) | C21—C19—C22 | 110.54 (12) |
C8—C7—P1 | 104.56 (10) | C21—C19—C20 | 109.04 (12) |
C7—C8—H8A | 109.5 | C22—C19—C20 | 109.04 (13) |
C7—C8—H8B | 109.5 | C21—C19—P2 | 113.53 (10) |
H8A—C8—H8B | 109.5 | C22—C19—P2 | 109.00 (10) |
C7—C8—H8C | 109.5 | C20—C19—P2 | 105.49 (9) |
H8A—C8—H8C | 109.5 | C19—C20—H20A | 109.5 |
H8B—C8—H8C | 109.5 | C19—C20—H20B | 109.5 |
C7—C9—H9A | 109.5 | H20A—C20—H20B | 109.5 |
C7—C9—H9B | 109.5 | C19—C20—H20C | 109.5 |
H9A—C9—H9B | 109.5 | H20A—C20—H20C | 109.5 |
C7—C9—H9C | 109.5 | H20B—C20—H20C | 109.5 |
H9A—C9—H9C | 109.5 | C19—C21—H21A | 109.5 |
H9B—C9—H9C | 109.5 | C19—C21—H21B | 109.5 |
C7—C10—H10A | 109.5 | H21A—C21—H21B | 109.5 |
C7—C10—H10B | 109.5 | C19—C21—H21C | 109.5 |
H10A—C10—H10B | 109.5 | H21A—C21—H21C | 109.5 |
C7—C10—H10C | 109.5 | H21B—C21—H21C | 109.5 |
H10A—C10—H10C | 109.5 | C19—C22—H22A | 109.5 |
H10B—C10—H10C | 109.5 | C19—C22—H22B | 109.5 |
C12—C11—C13 | 111.26 (12) | H22A—C22—H22B | 109.5 |
C12—C11—C14 | 108.92 (12) | C19—C22—H22C | 109.5 |
C13—C11—C14 | 108.27 (12) | H22A—C22—H22C | 109.5 |
C12—C11—P1 | 109.81 (10) | H22B—C22—H22C | 109.5 |
C13—C11—P1 | 113.17 (10) | C2—O1—P1 | 114.38 (7) |
C14—C11—P1 | 105.13 (9) | C4—O2—H2 | 108.4 (15) |
C11—C12—H12A | 109.5 | C6—O3—P2 | 114.27 (8) |
C11—C12—H12B | 109.5 | O1—P1—C11 | 100.72 (5) |
H12A—C12—H12B | 109.5 | O1—P1—C7 | 100.99 (5) |
C11—C12—H12C | 109.5 | C11—P1—C7 | 114.87 (6) |
H12A—C12—H12C | 109.5 | O1—P1—Pd1 | 104.76 (3) |
H12B—C12—H12C | 109.5 | C11—P1—Pd1 | 114.73 (5) |
C11—C13—H13A | 109.5 | C7—P1—Pd1 | 117.42 (4) |
C11—C13—H13B | 109.5 | O3—P2—C19 | 101.43 (6) |
H13A—C13—H13B | 109.5 | O3—P2—C15 | 101.10 (6) |
C11—C13—H13C | 109.5 | C19—P2—C15 | 114.50 (6) |
H13A—C13—H13C | 109.5 | O3—P2—Pd1 | 104.87 (3) |
H13B—C13—H13C | 109.5 | C19—P2—Pd1 | 115.77 (4) |
C11—C14—H14A | 109.5 | C15—P2—Pd1 | 116.12 (5) |
C11—C14—H14B | 109.5 | C1—Pd1—P1 | 80.11 (3) |
H14A—C14—H14B | 109.5 | C1—Pd1—P2 | 79.73 (3) |
C11—C14—H14C | 109.5 | P1—Pd1—P2 | 159.768 (12) |
H14A—C14—H14C | 109.5 | C1—Pd1—Cl1 | 179.06 (4) |
H14B—C14—H14C | 109.5 | P1—Pd1—Cl1 | 99.219 (13) |
C17—C15—C16 | 110.51 (13) | P2—Pd1—Cl1 | 100.957 (13) |
C17—C15—C18 | 109.05 (14) | ||
C6—C1—C2—O1 | 178.90 (10) | C14—C11—P1—Pd1 | −31.95 (10) |
Pd1—C1—C2—O1 | −0.73 (16) | C10—C7—P1—O1 | 61.39 (11) |
C6—C1—C2—C3 | −0.88 (18) | C9—C7—P1—O1 | −174.18 (11) |
Pd1—C1—C2—C3 | 179.49 (9) | C8—C7—P1—O1 | −57.15 (10) |
O1—C2—C3—C4 | −177.93 (11) | C10—C7—P1—C11 | −46.00 (13) |
C1—C2—C3—C4 | 1.85 (19) | C9—C7—P1—C11 | 78.44 (12) |
C2—C3—C4—O2 | 179.12 (11) | C8—C7—P1—C11 | −164.53 (10) |
C2—C3—C4—C5 | −0.89 (19) | C10—C7—P1—Pd1 | 174.54 (9) |
O2—C4—C5—C6 | 179.06 (11) | C9—C7—P1—Pd1 | −61.03 (12) |
C3—C4—C5—C6 | −0.93 (19) | C8—C7—P1—Pd1 | 56.00 (11) |
C4—C5—C6—O3 | −177.39 (11) | C6—O3—P2—C19 | 114.99 (9) |
C4—C5—C6—C1 | 1.99 (19) | C6—O3—P2—C15 | −126.92 (9) |
C2—C1—C6—C5 | −1.10 (18) | C6—O3—P2—Pd1 | −5.84 (9) |
Pd1—C1—C6—C5 | 178.53 (10) | C21—C19—P2—O3 | 65.88 (11) |
C2—C1—C6—O3 | 178.27 (11) | C22—C19—P2—O3 | −170.43 (10) |
Pd1—C1—C6—O3 | −2.10 (16) | C20—C19—P2—O3 | −53.46 (11) |
C3—C2—O1—P1 | −178.98 (9) | C21—C19—P2—C15 | −42.05 (12) |
C1—C2—O1—P1 | 1.23 (14) | C22—C19—P2—C15 | 81.64 (12) |
C5—C6—O3—P2 | −175.03 (9) | C20—C19—P2—C15 | −161.39 (10) |
C1—C6—O3—P2 | 5.56 (14) | C21—C19—P2—Pd1 | 178.72 (8) |
C2—O1—P1—C11 | −120.43 (9) | C22—C19—P2—Pd1 | −57.59 (11) |
C2—O1—P1—C7 | 121.36 (9) | C20—C19—P2—Pd1 | 59.38 (11) |
C2—O1—P1—Pd1 | −1.08 (9) | C17—C15—P2—O3 | −162.98 (11) |
C12—C11—P1—O1 | −163.04 (10) | C16—C15—P2—O3 | −37.91 (12) |
C13—C11—P1—O1 | −38.05 (11) | C18—C15—P2—O3 | 79.99 (11) |
C14—C11—P1—O1 | 79.93 (10) | C17—C15—P2—C19 | −54.84 (13) |
C12—C11—P1—C7 | −55.49 (12) | C16—C15—P2—C19 | 70.22 (12) |
C13—C11—P1—C7 | 69.50 (11) | C18—C15—P2—C19 | −171.88 (11) |
C14—C11—P1—C7 | −172.52 (9) | C17—C15—P2—Pd1 | 84.24 (11) |
C12—C11—P1—Pd1 | 85.08 (10) | C16—C15—P2—Pd1 | −150.70 (10) |
C13—C11—P1—Pd1 | −149.93 (9) | C18—C15—P2—Pd1 | −32.80 (12) |
D—H···A | D—H | H···A | D···A | D—H···A |
O2—H2···Cl1i | 0.79 (2) | 2.37 (2) | 3.1545 (11) | 174.2 (19) |
Symmetry code: (i) x+1/2, −y+1/2, z−1/2. |
[Pt(C22H39O3P2)Cl] | F(000) = 1280 |
Mr = 644.01 | Dx = 1.611 Mg m−3 |
Monoclinic, P21/n | Mo Kα radiation, λ = 0.71073 Å |
a = 9.7722 (8) Å | Cell parameters from 9874 reflections |
b = 20.1562 (16) Å | θ = 2.3–30.5° |
c = 13.9699 (11) Å | µ = 5.52 mm−1 |
β = 105.1634 (13)° | T = 150 K |
V = 2655.9 (4) Å3 | Prism, colourless |
Z = 4 | 0.34 × 0.21 × 0.15 mm |
Bruker APEXII CCD diffractometer | 6413 independent reflections |
Radiation source: fine-focus sealed tube | 5959 reflections with I > 2σ(I) |
Detector resolution: 8.3333 pixels mm-1 | Rint = 0.023 |
φ and ω scans | θmax = 28.0°, θmin = 1.8° |
Absorption correction: multi-scan (SADABS; Bruker, 2014) | h = −8→12 |
Tmin = 0.34, Tmax = 0.50 | k = −25→26 |
25029 measured reflections | l = −18→18 |
Refinement on F2 | 0 restraints |
Least-squares matrix: full | Hydrogen site location: mixed |
R[F2 > 2σ(F2)] = 0.016 | H atoms treated by a mixture of independent and constrained refinement |
wR(F2) = 0.037 | w = 1/[σ2(Fo2) + (0.0128P)2 + 2.002P] where P = (Fo2 + 2Fc2)/3 |
S = 1.02 | (Δ/σ)max = 0.001 |
6413 reflections | Δρmax = 0.87 e Å−3 |
278 parameters | Δρmin = −0.84 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 | ||
C1 | 0.2222 (2) | 0.29907 (9) | −0.06632 (13) | 0.0156 (4) | |
C2 | 0.3236 (2) | 0.27501 (9) | −0.11116 (14) | 0.0156 (4) | |
C3 | 0.3826 (2) | 0.31281 (9) | −0.17280 (14) | 0.0162 (4) | |
H3 | 0.4495 | 0.2943 | −0.2038 | 0.019* | |
C4 | 0.3405 (2) | 0.37898 (9) | −0.18783 (14) | 0.0165 (4) | |
C5 | 0.2411 (2) | 0.40605 (9) | −0.14397 (14) | 0.0186 (4) | |
H5 | 0.2139 | 0.4513 | −0.1539 | 0.022* | |
C6 | 0.1826 (2) | 0.36515 (9) | −0.08529 (14) | 0.0160 (4) | |
C7 | 0.2082 (2) | 0.09861 (10) | −0.10463 (16) | 0.0224 (4) | |
C8 | 0.1139 (3) | 0.13295 (13) | −0.19738 (17) | 0.0368 (6) | |
H8A | 0.1731 | 0.1604 | −0.2285 | 0.055* | |
H8B | 0.0438 | 0.1610 | −0.1780 | 0.055* | |
H8C | 0.0650 | 0.0993 | −0.2446 | 0.055* | |
C9 | 0.1142 (3) | 0.05599 (12) | −0.0570 (2) | 0.0389 (6) | |
H9A | 0.0616 | 0.0240 | −0.1057 | 0.058* | |
H9B | 0.0473 | 0.0845 | −0.0348 | 0.058* | |
H9C | 0.1736 | 0.0322 | 0.0000 | 0.058* | |
C10 | 0.3175 (3) | 0.05516 (11) | −0.13603 (18) | 0.0315 (5) | |
H10A | 0.3703 | 0.0290 | −0.0791 | 0.047* | |
H10B | 0.3835 | 0.0834 | −0.1597 | 0.047* | |
H10C | 0.2689 | 0.0252 | −0.1894 | 0.047* | |
C11 | 0.4449 (2) | 0.14387 (10) | 0.08141 (15) | 0.0219 (4) | |
C12 | 0.4032 (3) | 0.08751 (11) | 0.14229 (18) | 0.0338 (5) | |
H12A | 0.4785 | 0.0811 | 0.2035 | 0.051* | |
H12B | 0.3897 | 0.0465 | 0.1033 | 0.051* | |
H12C | 0.3147 | 0.0991 | 0.1589 | 0.051* | |
C13 | 0.5752 (2) | 0.12509 (11) | 0.04526 (18) | 0.0313 (5) | |
H13A | 0.6550 | 0.1151 | 0.1025 | 0.047* | |
H13B | 0.6005 | 0.1622 | 0.0079 | 0.047* | |
H13C | 0.5534 | 0.0860 | 0.0023 | 0.047* | |
C14 | 0.4811 (3) | 0.20604 (11) | 0.14718 (16) | 0.0282 (5) | |
H14A | 0.4008 | 0.2172 | 0.1740 | 0.042* | |
H14B | 0.5004 | 0.2432 | 0.1075 | 0.042* | |
H14C | 0.5650 | 0.1973 | 0.2019 | 0.042* | |
C15 | −0.1691 (2) | 0.34070 (11) | −0.02288 (16) | 0.0233 (4) | |
C16 | −0.2283 (3) | 0.40901 (12) | −0.06013 (19) | 0.0345 (5) | |
H16A | −0.3300 | 0.4053 | −0.0919 | 0.052* | |
H16B | −0.1795 | 0.4257 | −0.1083 | 0.052* | |
H16C | −0.2133 | 0.4398 | −0.0040 | 0.052* | |
C17 | −0.2449 (3) | 0.31316 (13) | 0.0515 (2) | 0.0392 (6) | |
H17A | −0.3454 | 0.3062 | 0.0183 | 0.059* | |
H17B | −0.2362 | 0.3448 | 0.1061 | 0.059* | |
H17C | −0.2018 | 0.2708 | 0.0778 | 0.059* | |
C18 | −0.1939 (3) | 0.29371 (14) | −0.1125 (2) | 0.0413 (6) | |
H18A | −0.1673 | 0.2484 | −0.0894 | 0.062* | |
H18B | −0.1360 | 0.3080 | −0.1563 | 0.062* | |
H18C | −0.2943 | 0.2947 | −0.1489 | 0.062* | |
C19 | 0.0864 (2) | 0.38351 (10) | 0.15143 (15) | 0.0221 (4) | |
C20 | 0.2450 (3) | 0.39706 (13) | 0.16472 (19) | 0.0371 (6) | |
H20A | 0.2850 | 0.4177 | 0.2295 | 0.056* | |
H20B | 0.2570 | 0.4270 | 0.1122 | 0.056* | |
H20C | 0.2941 | 0.3551 | 0.1609 | 0.056* | |
C21 | 0.0100 (3) | 0.44929 (10) | 0.15415 (16) | 0.0277 (5) | |
H21A | −0.0888 | 0.4407 | 0.1539 | 0.042* | |
H21B | 0.0125 | 0.4758 | 0.0958 | 0.042* | |
H21C | 0.0572 | 0.4736 | 0.2145 | 0.042* | |
C22 | 0.0683 (3) | 0.33748 (11) | 0.23488 (16) | 0.0349 (6) | |
H22A | 0.1101 | 0.3584 | 0.2992 | 0.052* | |
H22B | 0.1162 | 0.2952 | 0.2311 | 0.052* | |
H22C | −0.0328 | 0.3295 | 0.2276 | 0.052* | |
Cl1 | 0.03655 (8) | 0.17228 (3) | 0.12079 (5) | 0.03816 (15) | |
O1 | 0.36834 (15) | 0.20966 (6) | −0.09302 (10) | 0.0177 (3) | |
O2 | 0.39515 (17) | 0.42028 (7) | −0.24662 (11) | 0.0241 (3) | |
O3 | 0.07860 (15) | 0.39053 (6) | −0.04407 (10) | 0.0189 (3) | |
P1 | 0.28950 (5) | 0.16756 (2) | −0.02112 (4) | 0.01541 (10) | |
P2 | 0.02527 (5) | 0.33940 (2) | 0.03123 (4) | 0.01579 (10) | |
Pt1 | 0.13889 (2) | 0.24213 (2) | 0.01970 (2) | 0.01543 (3) | |
H2 | 0.441 (3) | 0.3988 (14) | −0.277 (2) | 0.039 (8)* |
U11 | U22 | U33 | U12 | U13 | U23 | |
C1 | 0.0183 (10) | 0.0158 (8) | 0.0138 (9) | 0.0009 (7) | 0.0064 (7) | 0.0017 (6) |
C2 | 0.0180 (10) | 0.0129 (8) | 0.0154 (9) | 0.0025 (7) | 0.0035 (7) | 0.0013 (7) |
C3 | 0.0164 (9) | 0.0175 (8) | 0.0170 (9) | 0.0027 (7) | 0.0085 (7) | 0.0014 (7) |
C4 | 0.0169 (10) | 0.0180 (8) | 0.0158 (9) | −0.0004 (7) | 0.0067 (7) | 0.0040 (7) |
C5 | 0.0225 (10) | 0.0144 (8) | 0.0206 (10) | 0.0029 (7) | 0.0085 (8) | 0.0031 (7) |
C6 | 0.0155 (9) | 0.0173 (8) | 0.0167 (9) | 0.0032 (7) | 0.0071 (7) | −0.0005 (7) |
C7 | 0.0268 (11) | 0.0183 (9) | 0.0243 (11) | −0.0033 (8) | 0.0106 (9) | −0.0060 (7) |
C8 | 0.0354 (14) | 0.0417 (13) | 0.0280 (13) | 0.0003 (11) | −0.0015 (10) | −0.0112 (10) |
C9 | 0.0459 (16) | 0.0342 (12) | 0.0454 (15) | −0.0206 (11) | 0.0273 (13) | −0.0161 (11) |
C10 | 0.0357 (14) | 0.0232 (10) | 0.0411 (14) | −0.0033 (9) | 0.0198 (11) | −0.0124 (9) |
C11 | 0.0255 (11) | 0.0191 (9) | 0.0199 (10) | 0.0026 (8) | 0.0037 (8) | 0.0056 (7) |
C12 | 0.0404 (14) | 0.0291 (11) | 0.0297 (13) | 0.0012 (10) | 0.0049 (11) | 0.0158 (9) |
C13 | 0.0257 (12) | 0.0321 (11) | 0.0343 (13) | 0.0089 (10) | 0.0045 (10) | 0.0051 (9) |
C14 | 0.0299 (12) | 0.0302 (11) | 0.0215 (11) | −0.0028 (9) | 0.0012 (9) | −0.0007 (8) |
C15 | 0.0172 (10) | 0.0271 (10) | 0.0264 (11) | −0.0007 (8) | 0.0074 (8) | −0.0006 (8) |
C16 | 0.0221 (12) | 0.0345 (12) | 0.0446 (15) | 0.0055 (10) | 0.0046 (10) | 0.0057 (10) |
C17 | 0.0244 (13) | 0.0469 (14) | 0.0515 (16) | −0.0041 (11) | 0.0191 (11) | 0.0086 (12) |
C18 | 0.0283 (13) | 0.0498 (15) | 0.0394 (15) | 0.0007 (12) | −0.0022 (11) | −0.0166 (12) |
C19 | 0.0281 (11) | 0.0186 (9) | 0.0201 (10) | 0.0026 (8) | 0.0074 (8) | −0.0023 (7) |
C20 | 0.0290 (13) | 0.0414 (13) | 0.0372 (14) | −0.0004 (11) | 0.0025 (10) | −0.0145 (11) |
C21 | 0.0392 (14) | 0.0184 (9) | 0.0279 (11) | 0.0038 (9) | 0.0131 (10) | −0.0032 (8) |
C22 | 0.0594 (17) | 0.0269 (11) | 0.0195 (11) | 0.0117 (11) | 0.0125 (11) | 0.0014 (8) |
Cl1 | 0.0641 (4) | 0.0222 (2) | 0.0437 (3) | −0.0029 (3) | 0.0417 (3) | 0.0040 (2) |
O1 | 0.0222 (7) | 0.0135 (6) | 0.0211 (7) | 0.0052 (5) | 0.0120 (6) | 0.0042 (5) |
O2 | 0.0329 (9) | 0.0173 (6) | 0.0297 (8) | 0.0041 (6) | 0.0217 (7) | 0.0064 (6) |
O3 | 0.0218 (7) | 0.0152 (6) | 0.0243 (7) | 0.0046 (5) | 0.0143 (6) | 0.0030 (5) |
P1 | 0.0197 (3) | 0.0121 (2) | 0.0163 (2) | 0.00103 (18) | 0.00787 (19) | 0.00132 (16) |
P2 | 0.0180 (3) | 0.0148 (2) | 0.0172 (2) | 0.00112 (18) | 0.00937 (19) | −0.00010 (17) |
Pt1 | 0.02031 (4) | 0.01324 (4) | 0.01583 (4) | 0.00074 (3) | 0.01022 (3) | 0.00099 (2) |
C1—C2 | 1.390 (3) | C14—H14A | 0.9800 |
C1—C6 | 1.393 (2) | C14—H14B | 0.9800 |
C1—Pt1 | 1.9841 (18) | C14—H14C | 0.9800 |
C2—C3 | 1.384 (3) | C15—C17 | 1.530 (3) |
C2—O1 | 1.390 (2) | C15—C16 | 1.531 (3) |
C3—C4 | 1.395 (2) | C15—C18 | 1.538 (3) |
C3—H3 | 0.9500 | C15—P2 | 1.852 (2) |
C4—O2 | 1.372 (2) | C16—H16A | 0.9800 |
C4—C5 | 1.389 (3) | C16—H16B | 0.9800 |
C5—C6 | 1.387 (3) | C16—H16C | 0.9800 |
C5—H5 | 0.9500 | C17—H17A | 0.9800 |
C6—O3 | 1.390 (2) | C17—H17B | 0.9800 |
C7—C9 | 1.531 (3) | C17—H17C | 0.9800 |
C7—C10 | 1.532 (3) | C18—H18A | 0.9800 |
C7—C8 | 1.543 (3) | C18—H18B | 0.9800 |
C7—P1 | 1.854 (2) | C18—H18C | 0.9800 |
C8—H8A | 0.9800 | C19—C21 | 1.527 (3) |
C8—H8B | 0.9800 | C19—C22 | 1.536 (3) |
C8—H8C | 0.9800 | C19—C20 | 1.537 (3) |
C9—H9A | 0.9800 | C19—P2 | 1.855 (2) |
C9—H9B | 0.9800 | C20—H20A | 0.9800 |
C9—H9C | 0.9800 | C20—H20B | 0.9800 |
C10—H10A | 0.9800 | C20—H20C | 0.9800 |
C10—H10B | 0.9800 | C21—H21A | 0.9800 |
C10—H10C | 0.9800 | C21—H21B | 0.9800 |
C11—C13 | 1.535 (3) | C21—H21C | 0.9800 |
C11—C12 | 1.537 (3) | C22—H22A | 0.9800 |
C11—C14 | 1.539 (3) | C22—H22B | 0.9800 |
C11—P1 | 1.857 (2) | C22—H22C | 0.9800 |
C12—H12A | 0.9800 | Cl1—Pt1 | 2.3907 (5) |
C12—H12B | 0.9800 | O1—P1 | 1.6514 (13) |
C12—H12C | 0.9800 | O2—H2 | 0.82 (3) |
C13—H13A | 0.9800 | O3—P2 | 1.6514 (13) |
C13—H13B | 0.9800 | P1—Pt1 | 2.2781 (5) |
C13—H13C | 0.9800 | P2—Pt1 | 2.2796 (5) |
C2—C1—C6 | 116.32 (16) | C16—C15—C18 | 108.19 (19) |
C2—C1—Pt1 | 121.64 (13) | C17—C15—P2 | 110.18 (16) |
C6—C1—Pt1 | 122.03 (14) | C16—C15—P2 | 114.05 (15) |
C3—C2—O1 | 118.22 (16) | C18—C15—P2 | 104.48 (15) |
C3—C2—C1 | 123.37 (17) | C15—C16—H16A | 109.5 |
O1—C2—C1 | 118.41 (16) | C15—C16—H16B | 109.5 |
C2—C3—C4 | 117.77 (17) | H16A—C16—H16B | 109.5 |
C2—C3—H3 | 121.1 | C15—C16—H16C | 109.5 |
C4—C3—H3 | 121.1 | H16A—C16—H16C | 109.5 |
O2—C4—C5 | 116.91 (16) | H16B—C16—H16C | 109.5 |
O2—C4—C3 | 121.65 (17) | C15—C17—H17A | 109.5 |
C5—C4—C3 | 121.45 (17) | C15—C17—H17B | 109.5 |
C6—C5—C4 | 118.14 (17) | H17A—C17—H17B | 109.5 |
C6—C5—H5 | 120.9 | C15—C17—H17C | 109.5 |
C4—C5—H5 | 120.9 | H17A—C17—H17C | 109.5 |
C5—C6—O3 | 119.03 (16) | H17B—C17—H17C | 109.5 |
C5—C6—C1 | 122.91 (17) | C15—C18—H18A | 109.5 |
O3—C6—C1 | 118.06 (16) | C15—C18—H18B | 109.5 |
C9—C7—C10 | 110.27 (18) | H18A—C18—H18B | 109.5 |
C9—C7—C8 | 108.8 (2) | C15—C18—H18C | 109.5 |
C10—C7—C8 | 108.90 (19) | H18A—C18—H18C | 109.5 |
C9—C7—P1 | 110.74 (15) | H18B—C18—H18C | 109.5 |
C10—C7—P1 | 113.09 (15) | C21—C19—C22 | 110.59 (18) |
C8—C7—P1 | 104.80 (14) | C21—C19—C20 | 109.09 (18) |
C7—C8—H8A | 109.5 | C22—C19—C20 | 109.2 (2) |
C7—C8—H8B | 109.5 | C21—C19—P2 | 113.26 (15) |
H8A—C8—H8B | 109.5 | C22—C19—P2 | 108.89 (14) |
C7—C8—H8C | 109.5 | C20—C19—P2 | 105.68 (14) |
H8A—C8—H8C | 109.5 | C19—C20—H20A | 109.5 |
H8B—C8—H8C | 109.5 | C19—C20—H20B | 109.5 |
C7—C9—H9A | 109.5 | H20A—C20—H20B | 109.5 |
C7—C9—H9B | 109.5 | C19—C20—H20C | 109.5 |
H9A—C9—H9B | 109.5 | H20A—C20—H20C | 109.5 |
C7—C9—H9C | 109.5 | H20B—C20—H20C | 109.5 |
H9A—C9—H9C | 109.5 | C19—C21—H21A | 109.5 |
H9B—C9—H9C | 109.5 | C19—C21—H21B | 109.5 |
C7—C10—H10A | 109.5 | H21A—C21—H21B | 109.5 |
C7—C10—H10B | 109.5 | C19—C21—H21C | 109.5 |
H10A—C10—H10B | 109.5 | H21A—C21—H21C | 109.5 |
C7—C10—H10C | 109.5 | H21B—C21—H21C | 109.5 |
H10A—C10—H10C | 109.5 | C19—C22—H22A | 109.5 |
H10B—C10—H10C | 109.5 | C19—C22—H22B | 109.5 |
C13—C11—C12 | 111.28 (18) | H22A—C22—H22B | 109.5 |
C13—C11—C14 | 108.47 (18) | C19—C22—H22C | 109.5 |
C12—C11—C14 | 108.90 (18) | H22A—C22—H22C | 109.5 |
C13—C11—P1 | 113.03 (15) | H22B—C22—H22C | 109.5 |
C12—C11—P1 | 109.56 (15) | C2—O1—P1 | 115.03 (11) |
C14—C11—P1 | 105.35 (14) | C4—O2—H2 | 110.2 (19) |
C11—C12—H12A | 109.5 | C6—O3—P2 | 114.89 (11) |
C11—C12—H12B | 109.5 | O1—P1—C7 | 101.18 (8) |
H12A—C12—H12B | 109.5 | O1—P1—C11 | 100.58 (8) |
C11—C12—H12C | 109.5 | C7—P1—C11 | 114.96 (9) |
H12A—C12—H12C | 109.5 | O1—P1—Pt1 | 104.36 (5) |
H12B—C12—H12C | 109.5 | C7—P1—Pt1 | 116.95 (7) |
C11—C13—H13A | 109.5 | C11—P1—Pt1 | 115.35 (7) |
C11—C13—H13B | 109.5 | O3—P2—C15 | 101.07 (9) |
H13A—C13—H13B | 109.5 | O3—P2—C19 | 101.36 (8) |
C11—C13—H13C | 109.5 | C15—P2—C19 | 114.56 (10) |
H13A—C13—H13C | 109.5 | O3—P2—Pt1 | 104.54 (5) |
H13B—C13—H13C | 109.5 | C15—P2—Pt1 | 116.74 (7) |
C11—C14—H14A | 109.5 | C19—P2—Pt1 | 115.39 (7) |
C11—C14—H14B | 109.5 | C1—Pt1—P1 | 80.54 (5) |
H14A—C14—H14B | 109.5 | C1—Pt1—P2 | 80.20 (5) |
C11—C14—H14C | 109.5 | P1—Pt1—P2 | 160.676 (17) |
H14A—C14—H14C | 109.5 | C1—Pt1—Cl1 | 178.95 (6) |
H14B—C14—H14C | 109.5 | P1—Pt1—Cl1 | 99.023 (19) |
C17—C15—C16 | 110.49 (19) | P2—Pt1—Cl1 | 100.257 (19) |
C17—C15—C18 | 109.2 (2) | ||
C6—C1—C2—C3 | −0.9 (3) | C8—C7—P1—Pt1 | 55.81 (16) |
Pt1—C1—C2—C3 | 178.98 (15) | C13—C11—P1—O1 | −38.88 (16) |
C6—C1—C2—O1 | 178.89 (16) | C12—C11—P1—O1 | −163.60 (15) |
Pt1—C1—C2—O1 | −1.2 (2) | C14—C11—P1—O1 | 79.40 (15) |
O1—C2—C3—C4 | −177.85 (17) | C13—C11—P1—C7 | 68.85 (17) |
C1—C2—C3—C4 | 2.0 (3) | C12—C11—P1—C7 | −55.87 (18) |
C2—C3—C4—O2 | 179.05 (18) | C14—C11—P1—C7 | −172.87 (14) |
C2—C3—C4—C5 | −1.0 (3) | C13—C11—P1—Pt1 | −150.45 (13) |
O2—C4—C5—C6 | 179.09 (18) | C12—C11—P1—Pt1 | 84.83 (15) |
C3—C4—C5—C6 | −0.8 (3) | C14—C11—P1—Pt1 | −32.18 (16) |
C4—C5—C6—O3 | −177.37 (17) | C6—O3—P2—C15 | −127.19 (14) |
C4—C5—C6—C1 | 2.0 (3) | C6—O3—P2—C19 | 114.69 (14) |
C2—C1—C6—C5 | −1.1 (3) | C6—O3—P2—Pt1 | −5.57 (14) |
Pt1—C1—C6—C5 | 178.99 (15) | C17—C15—P2—O3 | −163.37 (16) |
C2—C1—C6—O3 | 178.22 (17) | C16—C15—P2—O3 | −38.44 (17) |
Pt1—C1—C6—O3 | −1.7 (2) | C18—C15—P2—O3 | 79.49 (17) |
C3—C2—O1—P1 | −178.45 (14) | C17—C15—P2—C19 | −55.30 (19) |
C1—C2—O1—P1 | 1.7 (2) | C16—C15—P2—C19 | 69.62 (18) |
C5—C6—O3—P2 | −175.52 (15) | C18—C15—P2—C19 | −172.45 (16) |
C1—C6—O3—P2 | 5.1 (2) | C17—C15—P2—Pt1 | 83.99 (16) |
C2—O1—P1—C7 | 120.46 (14) | C16—C15—P2—Pt1 | −151.09 (14) |
C2—O1—P1—C11 | −121.21 (13) | C18—C15—P2—Pt1 | −33.16 (18) |
C2—O1—P1—Pt1 | −1.38 (13) | C21—C19—P2—O3 | 66.03 (17) |
C9—C7—P1—O1 | −173.96 (16) | C22—C19—P2—O3 | −170.48 (15) |
C10—C7—P1—O1 | 61.70 (17) | C20—C19—P2—O3 | −53.34 (16) |
C8—C7—P1—O1 | −56.78 (16) | C21—C19—P2—C15 | −41.87 (19) |
C9—C7—P1—C11 | 78.67 (19) | C22—C19—P2—C15 | 81.62 (17) |
C10—C7—P1—C11 | −45.66 (19) | C20—C19—P2—C15 | −161.23 (15) |
C8—C7—P1—C11 | −164.15 (15) | C21—C19—P2—Pt1 | 178.29 (13) |
C9—C7—P1—Pt1 | −61.38 (18) | C22—C19—P2—Pt1 | −58.23 (17) |
C10—C7—P1—Pt1 | 174.29 (13) | C20—C19—P2—Pt1 | 58.92 (16) |
D—H···A | D—H | H···A | D···A | D—H···A |
O2—H2···Cl1i | 0.82 (3) | 2.38 (3) | 3.1874 (16) | 170 (3) |
Symmetry code: (i) x+1/2, −y+1/2, z−1/2. |
Acknowledgements
We thank our technical and analytical staff for assistance. General support by LIKAT is gratefully acknowledged. The publication of this article was funded by the Open Access Fund of the Leibniz Association.
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