metal-organic compounds
trans-Chlorido(4-fluorobenzenethiolato-κS)bis(triphenylphosphane-κP)palladium(II) methanol hemisolvate
aEscuela Nacional de Ciencias Biológicas, IPN, Departamento de Química Orgánica, Caprio y Plan de Ayala S/N, Colonia Santo Tomás, 11340 México DF, Mexico, bUniversidad Politécnica de Tlaxcala, Av. Universidad Politécnica de Tlaxcala No. 1, San Pedro Xalcaltzinco Municipio de Tepeyanco, Tlaxcala, CP 90180, Mexico, and cInstituto de Química, Universidad Nacional Autónoma de México, Circuito exterior, Ciudad Universitaria, México, DF 04510, Mexico
*Correspondence e-mail: aavilas@ipn.mx
The title compound, [Pd(SC6H4F-p)Cl(PPh3)2]·0.5CH3OH, features a PdII complex with two triphenylphosphane (PPh3) ligands arranged in a trans conformation, with one chloride and one 4-fluorobenzenethiolate ligand completing the coordination sphere, giving rise to a slightly distorted square-planar geometry of the PdII ion. The methanol solvent molecule is disordered about an inversion centre with an occupancy of 0.25 for each molecule. In the crystal, weak C—H⋯Cl hydrogen-bonding interactions between the complex molecules generate chain frameworks parallel to [010].
CCDC reference: 984868
Related literature
For palladium complexes in catalysis, see: Frisch & Beller (2005); Yin & Liebscher (2007); Knochel & Singer (1993); Surry & Buchwald (2008). For related compounds, see: Jones et al. (2000); Alvarez-Larena et al. (1993).
Experimental
Crystal data
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Data collection: SMART (Bruker, 2007); cell SAINT (Bruker, 2007); data reduction: SAINT; program(s) used to solve structure: SHELXTL (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 for Windows (Farrugia, 2012) and DIAMOND (Brandenburg, 2006); software used to prepare material for publication: SHELXTL) and PLATON (Spek, 2009).
Supporting information
CCDC reference: 984868
10.1107/S1600536814002499/hp2065sup1.cif
contains datablock I. DOI:Structure factors: contains datablock I. DOI: 10.1107/S1600536814002499/hp2065Isup2.hkl
The high efficiency of palladium complexes in C—C cross coupling reactions is well known, for example in the Suzuki-Miyaura (Frisch & Beller, 2005), Mizoroki-Heck (Yin & Liebscher, 2007) and Negishi reactions (Knochel & Singer, 1993), as well as for the formation of C-Heteroatom bonds as in the Buchwald–Hartwig couplings (Surry & Buchwald, 2008). In this context, different research groups have devoted their research efforts to the synthesis of new palladium complexes with a variety of ligands. Therefore, in this opportunity we would like to report the
of the PdII complex trans-[Pd(SC6H4F-p)(Cl)(PPh3)2] ·0.5CH3OH.To a suspension consisting of PdCl2 (0.072 g, 0.41 mmol) and Na2CO3 (0.050 g, 0.0471 mmol) in 15 mL of toluene was added dropwise under magnetic stirring a toluene solution (5 mL) of an isomeric mix of (3-ethenylbenzyl)(4-fluorophenyl)sulfane and (4-ethenylbenzyl)(4-fluorophenyl)sulfane (60:40) (0.100 g, 0.41 mmol). The resulting mixture was set to reflux for 4 hours. After this time the reaction mixture was allowed to cool down to room temperature, filtered and the solid product washed with CHCl3. The insoluble reddish solid was then suspended in 15 mL of CHCl3 and then treated with Ph3P (0.215 g, 820 mmol). The reaction was allowed to proceed under stirring until the solid was completely dissolved. This solution was then filtered through a short plug of celite and CH3OH was added to promote precipitation. Slow evaporation of the solvent at room temperature produced brown crystals for X-ray
of trans-[Pd(SC6H4F-p)(Cl)(PPh3)2] ·0.5CH3OH.Crystal data, data collection and structure
details are summarized in Table 2. H atoms were included in calculated positions (C—H = 0.93 Å for aromatic H) and refined using a riding model with Uiso(H) = 1.2 Ueq of carrier atoms. The CH3OH solvent is disordered over two sets of sites in a 0.25 : 0.25 ratio.The compound trans-[Pd(SC6H4F-p)(Cl)(PPh3)2] ·0.5CH3OH crystallized in a monoclinic system including the complex trans-[Pd(SC6H4F-p)(Cl)(PPh3)2] and half molecule of methanol in the
The Pd2+ ion exhibits a slightly distorted square-planar PdClSP2 geometry, with one chloride and one p-fluorobenzenethiolate ligand and two molecules of triphenylphosphane in conformation completing the coordination sphere. The bond distances Pd—Cl and Pd—S are 2.3269 (11) and 2.2977 (11) Å, respectively, and the Pd—P distances are 2.3432 (11) and 2.3342 (11) Å. These distances are comparable to those found in the structures of the related compounds trans-[Pd(SC6H4Cl-p)(Cl)(PPh3)2] (Jones et al., 2000) and trans-[Pd(SC6H5)(Cl)(PPh3)2] (Alvarez-Larena et al., 1993).The p-fluorobenzenethiolate presents an intramolecular π-π interaction with one phenyl ring of the tripehylphosphane ligand. The distance between centroids Cg(C1—C6)-Cg(C7—C12) is 3.677 (3) Å. The structure is stabilized by weak C—H···Cl hydrogen bonding interactions between the complex molecules generate chain frameworks parallel to [010]. The methanol molecule is disordered over two positions in a 0.25:0.25 ratio.
Data collection: SMART (Bruker, 2007); cell
SAINT (Bruker, 2007); data reduction: SAINT (Bruker, 2007); program(s) used to solve structure: SHELXTL (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 for Windows (Farrugia, 2012) and DIAMOND (Brandenburg, 2006); software used to prepare material for publication: SHELXTL (Sheldrick, 2008) and PLATON (Spek, 2009).[Pd(C6H4FS)Cl(C18H15P)2]·0.5CH4O | F(000) = 1652 |
Mr = 809.56 | Dx = 1.413 Mg m−3 |
Monoclinic, P21/c | Mo Kα radiation, λ = 0.71073 Å |
a = 18.9189 (16) Å | Cell parameters from 8442 reflections |
b = 9.6909 (8) Å | θ = 2.3–25.1° |
c = 21.6179 (18) Å | µ = 0.73 mm−1 |
β = 106.212 (1)° | T = 298 K |
V = 3805.8 (6) Å3 | Plates, dark-pink |
Z = 4 | 0.30 × 0.20 × 0.08 mm |
Bruker SMART APEX CCD diffractometer | 6950 independent reflections |
Radiation source: fine-focus sealed tube | 5392 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.052 |
Detector resolution: 8.333 pixels mm-1 | θmax = 25.4°, θmin = 2.0° |
ω–scans | h = −22→22 |
Absorption correction: multi-scan (SADABS; Sheldrick, 2008) | k = −11→11 |
Tmin = 0.822, Tmax = 0.947 | l = −26→26 |
30189 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)] = 0.043 | Hydrogen site location: mixed |
wR(F2) = 0.110 | H-atom parameters constrained |
S = 1.02 | w = 1/[σ2(Fo2) + (0.0613P)2] where P = (Fo2 + 2Fc2)/3 |
6950 reflections | (Δ/σ)max < 0.001 |
469 parameters | Δρmax = 0.57 e Å−3 |
33 restraints | Δρmin = −0.28 e Å−3 |
[Pd(C6H4FS)Cl(C18H15P)2]·0.5CH4O | V = 3805.8 (6) Å3 |
Mr = 809.56 | Z = 4 |
Monoclinic, P21/c | Mo Kα radiation |
a = 18.9189 (16) Å | µ = 0.73 mm−1 |
b = 9.6909 (8) Å | T = 298 K |
c = 21.6179 (18) Å | 0.30 × 0.20 × 0.08 mm |
β = 106.212 (1)° |
Bruker SMART APEX CCD diffractometer | 6950 independent reflections |
Absorption correction: multi-scan (SADABS; Sheldrick, 2008) | 5392 reflections with I > 2σ(I) |
Tmin = 0.822, Tmax = 0.947 | Rint = 0.052 |
30189 measured reflections |
R[F2 > 2σ(F2)] = 0.043 | 33 restraints |
wR(F2) = 0.110 | H-atom parameters constrained |
S = 1.02 | Δρmax = 0.57 e Å−3 |
6950 reflections | Δρmin = −0.28 e Å−3 |
469 parameters |
Geometry. All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell e.s.d.'s are taken into account individually in the estimation of e.s.d.'s in distances, angles and torsion angles; correlations between e.s.d.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell e.s.d.'s is used for estimating e.s.d.'s involving l.s. planes. |
x | y | z | Uiso*/Ueq | Occ. (<1) | |
Pd1 | 0.24393 (2) | 0.02208 (3) | 0.14849 (2) | 0.04003 (11) | |
Cl1 | 0.19542 (6) | 0.18164 (10) | 0.06730 (5) | 0.0558 (3) | |
S1 | 0.29295 (6) | −0.13516 (10) | 0.22852 (5) | 0.0519 (2) | |
P1 | 0.15593 (5) | 0.09096 (10) | 0.19997 (5) | 0.0437 (2) | |
P2 | 0.33009 (5) | −0.06767 (10) | 0.10028 (5) | 0.0424 (2) | |
F1 | 0.44844 (17) | 0.1686 (4) | 0.46211 (14) | 0.1094 (11) | |
C1 | 0.3380 (2) | −0.0375 (4) | 0.29652 (19) | 0.0517 (10) | |
C2 | 0.3650 (2) | 0.0954 (5) | 0.2943 (2) | 0.0615 (11) | |
H2 | 0.3584 | 0.1383 | 0.2547 | 0.074* | |
C3 | 0.4012 (2) | 0.1645 (5) | 0.3494 (2) | 0.0658 (12) | |
H3 | 0.4181 | 0.2540 | 0.3473 | 0.079* | |
C4 | 0.4120 (2) | 0.1002 (6) | 0.4074 (2) | 0.0736 (13) | |
C5 | 0.3885 (3) | −0.0311 (6) | 0.4122 (2) | 0.0740 (13) | |
H5 | 0.3977 | −0.0742 | 0.4521 | 0.089* | |
C6 | 0.3510 (2) | −0.0987 (5) | 0.3569 (2) | 0.0623 (11) | |
H6 | 0.3338 | −0.1876 | 0.3599 | 0.075* | |
C7 | 0.1691 (2) | 0.0487 (4) | 0.28479 (19) | 0.0495 (9) | |
C8 | 0.1943 (2) | 0.1436 (5) | 0.33324 (19) | 0.0658 (12) | |
H8 | 0.2035 | 0.2338 | 0.3230 | 0.079* | |
C9 | 0.2059 (3) | 0.1061 (7) | 0.3973 (2) | 0.0877 (16) | |
H9 | 0.2233 | 0.1714 | 0.4295 | 0.105* | |
C10 | 0.1924 (3) | −0.0239 (8) | 0.4135 (3) | 0.098 (2) | |
H10 | 0.2003 | −0.0483 | 0.4565 | 0.117* | |
C11 | 0.1666 (3) | −0.1204 (6) | 0.3652 (3) | 0.0883 (16) | |
H11 | 0.1560 | −0.2095 | 0.3759 | 0.106* | |
C12 | 0.1564 (2) | −0.0862 (5) | 0.3015 (2) | 0.0677 (12) | |
H12 | 0.1411 | −0.1529 | 0.2696 | 0.081* | |
C13 | 0.1360 (2) | 0.2754 (4) | 0.19518 (17) | 0.0507 (9) | |
C14 | 0.0647 (3) | 0.3255 (5) | 0.1726 (2) | 0.0717 (13) | |
H14 | 0.0255 | 0.2641 | 0.1600 | 0.086* | |
C15 | 0.0516 (4) | 0.4662 (6) | 0.1687 (3) | 0.1000 (19) | |
H15 | 0.0037 | 0.4986 | 0.1526 | 0.120* | |
C16 | 0.1081 (5) | 0.5574 (6) | 0.1883 (3) | 0.099 (2) | |
H16 | 0.0987 | 0.6518 | 0.1858 | 0.119* | |
C17 | 0.1799 (4) | 0.5098 (5) | 0.2121 (3) | 0.0893 (17) | |
H17 | 0.2186 | 0.5716 | 0.2266 | 0.107* | |
C18 | 0.1931 (3) | 0.3675 (5) | 0.2140 (2) | 0.0670 (12) | |
H18 | 0.2412 | 0.3350 | 0.2281 | 0.080* | |
C19 | 0.0685 (2) | 0.0080 (4) | 0.1601 (2) | 0.0574 (11) | |
C20 | 0.0565 (3) | −0.0437 (5) | 0.0987 (2) | 0.0761 (14) | |
H20 | 0.0931 | −0.0360 | 0.0779 | 0.091* | |
C21 | −0.0097 (3) | −0.1070 (7) | 0.0675 (3) | 0.103 (2) | |
H21 | −0.0182 | −0.1391 | 0.0255 | 0.123* | |
C22 | −0.0624 (3) | −0.1214 (8) | 0.0995 (3) | 0.117 (2) | |
H22 | −0.1064 | −0.1657 | 0.0793 | 0.141* | |
C23 | −0.0514 (3) | −0.0726 (8) | 0.1596 (3) | 0.116 (2) | |
H23 | −0.0876 | −0.0830 | 0.1808 | 0.139* | |
C24 | 0.0138 (3) | −0.0069 (6) | 0.1899 (3) | 0.0874 (17) | |
H24 | 0.0208 | 0.0278 | 0.2313 | 0.105* | |
C25 | 0.4207 (2) | −0.0086 (4) | 0.14525 (19) | 0.0488 (9) | |
C26 | 0.4425 (2) | 0.1222 (4) | 0.1350 (2) | 0.0678 (12) | |
H26 | 0.4125 | 0.1769 | 0.1029 | 0.081* | |
C27 | 0.5096 (3) | 0.1733 (5) | 0.1729 (3) | 0.0836 (15) | |
H27 | 0.5242 | 0.2621 | 0.1657 | 0.100* | |
C28 | 0.5541 (3) | 0.0943 (6) | 0.2205 (3) | 0.0838 (16) | |
H28 | 0.5993 | 0.1287 | 0.2447 | 0.101* | |
C29 | 0.5330 (3) | −0.0320 (6) | 0.2322 (2) | 0.0754 (14) | |
H29 | 0.5628 | −0.0841 | 0.2655 | 0.091* | |
C30 | 0.4664 (2) | −0.0865 (5) | 0.1947 (2) | 0.0625 (11) | |
H30 | 0.4525 | −0.1752 | 0.2028 | 0.075* | |
C31 | 0.33212 (19) | −0.2558 (4) | 0.09877 (16) | 0.0434 (8) | |
C32 | 0.3926 (2) | −0.3279 (4) | 0.09171 (19) | 0.0536 (10) | |
H32 | 0.4351 | −0.2801 | 0.0910 | 0.064* | |
C33 | 0.3907 (3) | −0.4696 (4) | 0.0857 (2) | 0.0641 (11) | |
H33 | 0.4318 | −0.5175 | 0.0817 | 0.077* | |
C34 | 0.3277 (3) | −0.5392 (4) | 0.0857 (2) | 0.0674 (12) | |
H34 | 0.3263 | −0.6347 | 0.0815 | 0.081* | |
C35 | 0.2672 (3) | −0.4707 (4) | 0.0917 (2) | 0.0601 (11) | |
H35 | 0.2246 | −0.5193 | 0.0913 | 0.072* | |
C36 | 0.2691 (2) | −0.3287 (4) | 0.09834 (18) | 0.0530 (10) | |
H36 | 0.2278 | −0.2819 | 0.1025 | 0.064* | |
C37 | 0.3254 (2) | −0.0314 (4) | 0.01670 (19) | 0.0487 (9) | |
C38 | 0.2591 (3) | −0.0288 (4) | −0.0293 (2) | 0.0655 (12) | |
H38 | 0.2160 | −0.0342 | −0.0167 | 0.079* | |
C39 | 0.2546 (3) | −0.0181 (5) | −0.0945 (2) | 0.0776 (14) | |
H39 | 0.2090 | −0.0179 | −0.1252 | 0.093* | |
C40 | 0.3169 (3) | −0.0081 (5) | −0.1131 (3) | 0.0799 (15) | |
H40 | 0.3138 | 0.0013 | −0.1566 | 0.096* | |
C41 | 0.3848 (3) | −0.0118 (6) | −0.0684 (3) | 0.0891 (17) | |
H41 | 0.4274 | −0.0064 | −0.0817 | 0.107* | |
C42 | 0.3896 (3) | −0.0232 (5) | −0.0041 (2) | 0.0780 (14) | |
H42 | 0.4356 | −0.0257 | 0.0260 | 0.094* | |
O1 | 0.0542 (7) | 1.0384 (15) | 0.5041 (6) | 0.077 (4) | 0.25 |
H1 | 0.0112 | 1.0626 | 0.4896 | 0.115* | 0.25 |
C43 | 0.0682 (13) | 0.889 (3) | 0.5018 (13) | 0.071 (4) | 0.25 |
H43A | 0.0231 | 0.8397 | 0.4971 | 0.086* | 0.25 |
H43B | 0.1036 | 0.8617 | 0.5409 | 0.086* | 0.25 |
H43C | 0.0869 | 0.8698 | 0.4658 | 0.086* | 0.25 |
O1B | 0.0386 (8) | 0.928 (2) | 0.5026 (8) | 0.084 (4) | 0.25 |
H1B | 0.0521 | 0.9888 | 0.4820 | 0.125* | 0.25 |
C43B | 0.0690 (11) | 0.808 (2) | 0.4885 (10) | 0.079 (4) | 0.25 |
H43D | 0.0340 | 0.7605 | 0.4542 | 0.094* | 0.25 |
H43E | 0.0821 | 0.7499 | 0.5260 | 0.094* | 0.25 |
H43F | 0.1123 | 0.8284 | 0.4752 | 0.094* | 0.25 |
U11 | U22 | U33 | U12 | U13 | U23 | |
Pd1 | 0.04087 (17) | 0.03949 (17) | 0.03993 (17) | −0.00118 (12) | 0.01160 (12) | −0.00155 (12) |
Cl1 | 0.0686 (6) | 0.0477 (6) | 0.0503 (6) | 0.0034 (5) | 0.0151 (5) | 0.0052 (4) |
S1 | 0.0627 (6) | 0.0458 (5) | 0.0468 (6) | 0.0065 (5) | 0.0147 (5) | 0.0020 (4) |
P1 | 0.0414 (5) | 0.0484 (6) | 0.0416 (5) | −0.0008 (4) | 0.0119 (4) | −0.0012 (4) |
P2 | 0.0429 (5) | 0.0412 (5) | 0.0446 (5) | −0.0017 (4) | 0.0147 (4) | −0.0026 (4) |
F1 | 0.100 (2) | 0.147 (3) | 0.0691 (19) | −0.022 (2) | 0.0042 (17) | −0.0266 (19) |
C1 | 0.047 (2) | 0.056 (2) | 0.053 (2) | 0.0114 (18) | 0.0148 (18) | 0.0026 (19) |
C2 | 0.055 (2) | 0.069 (3) | 0.060 (3) | 0.003 (2) | 0.016 (2) | 0.006 (2) |
C3 | 0.054 (3) | 0.076 (3) | 0.064 (3) | −0.011 (2) | 0.011 (2) | −0.008 (2) |
C4 | 0.058 (3) | 0.102 (4) | 0.053 (3) | −0.002 (3) | 0.002 (2) | −0.016 (3) |
C5 | 0.072 (3) | 0.095 (4) | 0.049 (3) | 0.017 (3) | 0.008 (2) | 0.007 (3) |
C6 | 0.069 (3) | 0.066 (3) | 0.052 (3) | 0.011 (2) | 0.018 (2) | 0.005 (2) |
C7 | 0.046 (2) | 0.059 (3) | 0.046 (2) | 0.0070 (18) | 0.0166 (18) | 0.0041 (19) |
C8 | 0.074 (3) | 0.078 (3) | 0.045 (2) | 0.021 (2) | 0.015 (2) | −0.005 (2) |
C9 | 0.089 (4) | 0.118 (5) | 0.054 (3) | 0.032 (3) | 0.015 (3) | −0.008 (3) |
C10 | 0.099 (4) | 0.146 (6) | 0.051 (3) | 0.033 (4) | 0.027 (3) | 0.027 (4) |
C11 | 0.090 (4) | 0.102 (4) | 0.077 (4) | 0.008 (3) | 0.029 (3) | 0.038 (3) |
C12 | 0.068 (3) | 0.077 (3) | 0.057 (3) | 0.000 (2) | 0.017 (2) | 0.007 (2) |
C13 | 0.064 (3) | 0.052 (2) | 0.041 (2) | 0.006 (2) | 0.0214 (19) | −0.0009 (18) |
C14 | 0.075 (3) | 0.068 (3) | 0.070 (3) | 0.021 (2) | 0.016 (2) | 0.001 (2) |
C15 | 0.123 (5) | 0.085 (4) | 0.088 (4) | 0.049 (4) | 0.024 (4) | 0.004 (3) |
C16 | 0.171 (7) | 0.058 (3) | 0.076 (4) | 0.031 (4) | 0.045 (4) | 0.009 (3) |
C17 | 0.134 (5) | 0.067 (4) | 0.076 (4) | −0.018 (3) | 0.045 (4) | −0.008 (3) |
C18 | 0.078 (3) | 0.055 (3) | 0.073 (3) | −0.003 (2) | 0.029 (3) | 0.000 (2) |
C19 | 0.048 (2) | 0.069 (3) | 0.052 (3) | −0.0102 (19) | 0.010 (2) | 0.003 (2) |
C20 | 0.067 (3) | 0.094 (4) | 0.064 (3) | −0.030 (3) | 0.013 (2) | −0.005 (3) |
C21 | 0.093 (4) | 0.137 (5) | 0.068 (3) | −0.055 (4) | 0.005 (3) | −0.010 (3) |
C22 | 0.084 (4) | 0.173 (7) | 0.083 (4) | −0.069 (4) | 0.002 (3) | 0.009 (4) |
C23 | 0.054 (3) | 0.208 (7) | 0.083 (4) | −0.041 (4) | 0.013 (3) | 0.023 (5) |
C24 | 0.053 (3) | 0.145 (5) | 0.063 (3) | −0.022 (3) | 0.014 (2) | −0.003 (3) |
C25 | 0.050 (2) | 0.044 (2) | 0.054 (2) | −0.0033 (17) | 0.0162 (19) | −0.0112 (18) |
C26 | 0.060 (3) | 0.052 (3) | 0.095 (3) | −0.006 (2) | 0.027 (2) | −0.005 (2) |
C27 | 0.078 (3) | 0.062 (3) | 0.118 (5) | −0.028 (3) | 0.039 (3) | −0.026 (3) |
C28 | 0.052 (3) | 0.093 (4) | 0.104 (4) | −0.022 (3) | 0.019 (3) | −0.046 (4) |
C29 | 0.060 (3) | 0.095 (4) | 0.066 (3) | −0.010 (3) | 0.008 (2) | −0.022 (3) |
C30 | 0.057 (3) | 0.069 (3) | 0.057 (3) | −0.011 (2) | 0.009 (2) | −0.009 (2) |
C31 | 0.048 (2) | 0.042 (2) | 0.039 (2) | −0.0035 (16) | 0.0102 (16) | −0.0041 (16) |
C32 | 0.047 (2) | 0.053 (2) | 0.061 (3) | 0.0034 (18) | 0.0162 (19) | 0.001 (2) |
C33 | 0.068 (3) | 0.053 (3) | 0.072 (3) | 0.016 (2) | 0.020 (2) | 0.000 (2) |
C34 | 0.089 (4) | 0.042 (2) | 0.071 (3) | 0.001 (2) | 0.023 (3) | −0.002 (2) |
C35 | 0.070 (3) | 0.046 (2) | 0.067 (3) | −0.018 (2) | 0.025 (2) | −0.006 (2) |
C36 | 0.051 (2) | 0.053 (2) | 0.060 (3) | −0.0027 (18) | 0.022 (2) | −0.0062 (19) |
C37 | 0.057 (2) | 0.042 (2) | 0.049 (2) | 0.0004 (18) | 0.019 (2) | 0.0006 (17) |
C38 | 0.067 (3) | 0.070 (3) | 0.061 (3) | −0.004 (2) | 0.019 (2) | −0.007 (2) |
C39 | 0.081 (3) | 0.093 (4) | 0.053 (3) | 0.010 (3) | 0.008 (3) | −0.001 (2) |
C40 | 0.109 (4) | 0.080 (4) | 0.056 (3) | 0.009 (3) | 0.031 (3) | 0.007 (2) |
C41 | 0.086 (4) | 0.126 (5) | 0.067 (3) | 0.007 (3) | 0.040 (3) | 0.013 (3) |
C42 | 0.061 (3) | 0.112 (4) | 0.064 (3) | 0.004 (3) | 0.021 (2) | 0.007 (3) |
O1 | 0.051 (6) | 0.131 (10) | 0.048 (5) | −0.026 (7) | 0.014 (5) | 0.006 (7) |
C43 | 0.040 (7) | 0.134 (10) | 0.045 (6) | −0.025 (9) | 0.020 (7) | 0.000 (8) |
O1B | 0.055 (7) | 0.153 (11) | 0.048 (5) | −0.042 (8) | 0.023 (6) | 0.003 (7) |
C43B | 0.051 (7) | 0.141 (12) | 0.045 (8) | −0.036 (9) | 0.016 (6) | 0.022 (9) |
Pd1—S1 | 2.2976 (10) | C21—H21 | 0.9300 |
Pd1—Cl1 | 2.3269 (10) | C22—C23 | 1.345 (8) |
Pd1—P2 | 2.3342 (10) | C22—H22 | 0.9300 |
Pd1—P1 | 2.3432 (10) | C23—C24 | 1.380 (7) |
S1—C1 | 1.756 (4) | C23—H23 | 0.9300 |
P1—C13 | 1.824 (4) | C24—H24 | 0.9300 |
P1—C19 | 1.825 (4) | C25—C26 | 1.369 (5) |
P1—C7 | 1.827 (4) | C25—C30 | 1.394 (6) |
P2—C25 | 1.812 (4) | C26—C27 | 1.396 (6) |
P2—C37 | 1.818 (4) | C26—H26 | 0.9300 |
P2—C31 | 1.824 (4) | C27—C28 | 1.368 (7) |
F1—C4 | 1.364 (5) | C27—H27 | 0.9300 |
C1—C2 | 1.391 (6) | C28—C29 | 1.333 (7) |
C1—C6 | 1.392 (6) | C28—H28 | 0.9300 |
C2—C3 | 1.371 (6) | C29—C30 | 1.398 (6) |
C2—H2 | 0.9300 | C29—H29 | 0.9300 |
C3—C4 | 1.362 (6) | C30—H30 | 0.9300 |
C3—H3 | 0.9300 | C31—C36 | 1.384 (5) |
C4—C5 | 1.362 (7) | C31—C32 | 1.385 (5) |
C5—C6 | 1.374 (6) | C32—C33 | 1.380 (5) |
C5—H5 | 0.9300 | C32—H32 | 0.9300 |
C6—H6 | 0.9300 | C33—C34 | 1.368 (6) |
C7—C8 | 1.375 (6) | C33—H33 | 0.9300 |
C7—C12 | 1.394 (6) | C34—C35 | 1.362 (6) |
C8—C9 | 1.389 (6) | C34—H34 | 0.9300 |
C8—H8 | 0.9300 | C35—C36 | 1.384 (5) |
C9—C10 | 1.351 (8) | C35—H35 | 0.9300 |
C9—H9 | 0.9300 | C36—H36 | 0.9300 |
C10—C11 | 1.386 (8) | C37—C38 | 1.366 (6) |
C10—H10 | 0.9300 | C37—C42 | 1.410 (6) |
C11—C12 | 1.376 (6) | C38—C39 | 1.394 (6) |
C11—H11 | 0.9300 | C38—H38 | 0.9300 |
C12—H12 | 0.9300 | C39—C40 | 1.349 (7) |
C13—C18 | 1.372 (6) | C39—H39 | 0.9300 |
C13—C14 | 1.388 (6) | C40—C41 | 1.376 (7) |
C14—C15 | 1.384 (7) | C40—H40 | 0.9300 |
C14—H14 | 0.9300 | C41—C42 | 1.371 (7) |
C15—C16 | 1.361 (9) | C41—H41 | 0.9300 |
C15—H15 | 0.9300 | C42—H42 | 0.9300 |
C16—C17 | 1.390 (9) | O1—C43 | 1.47 (2) |
C16—H16 | 0.9300 | O1—H1 | 0.8200 |
C17—C18 | 1.400 (7) | C43—H43A | 0.9600 |
C17—H17 | 0.9300 | C43—H43B | 0.9600 |
C18—H18 | 0.9300 | C43—H43C | 0.9600 |
C19—C24 | 1.370 (6) | O1B—C43B | 1.37 (2) |
C19—C20 | 1.376 (6) | O1B—H1B | 0.8199 |
C20—C21 | 1.389 (6) | C43B—H43D | 0.9600 |
C20—H20 | 0.9300 | C43B—H43E | 0.9600 |
C21—C22 | 1.368 (8) | C43B—H43F | 0.9600 |
S1—Pd1—Cl1 | 179.44 (4) | C22—C21—H21 | 120.5 |
S1—Pd1—P2 | 84.47 (4) | C20—C21—H21 | 120.5 |
Cl1—Pd1—P2 | 95.07 (4) | C23—C22—C21 | 121.0 (5) |
S1—Pd1—P1 | 91.28 (4) | C23—C22—H22 | 119.5 |
Cl1—Pd1—P1 | 89.20 (4) | C21—C22—H22 | 119.5 |
P2—Pd1—P1 | 174.61 (4) | C22—C23—C24 | 119.8 (5) |
C1—S1—Pd1 | 105.81 (14) | C22—C23—H23 | 120.1 |
C13—P1—C19 | 105.03 (19) | C24—C23—H23 | 120.1 |
C13—P1—C7 | 104.19 (17) | C19—C24—C23 | 121.2 (5) |
C19—P1—C7 | 103.12 (19) | C19—C24—H24 | 119.4 |
C13—P1—Pd1 | 114.53 (12) | C23—C24—H24 | 119.4 |
C19—P1—Pd1 | 108.71 (14) | C26—C25—C30 | 118.4 (4) |
C7—P1—Pd1 | 119.79 (12) | C26—C25—P2 | 119.2 (3) |
C25—P2—C37 | 104.38 (18) | C30—C25—P2 | 122.1 (3) |
C25—P2—C31 | 107.68 (17) | C25—C26—C27 | 119.9 (5) |
C37—P2—C31 | 99.83 (16) | C25—C26—H26 | 120.1 |
C25—P2—Pd1 | 108.49 (12) | C27—C26—H26 | 120.1 |
C37—P2—Pd1 | 121.69 (13) | C28—C27—C26 | 120.7 (5) |
C31—P2—Pd1 | 113.66 (12) | C28—C27—H27 | 119.6 |
C2—C1—C6 | 117.1 (4) | C26—C27—H27 | 119.6 |
C2—C1—S1 | 124.6 (3) | C29—C28—C27 | 120.1 (4) |
C6—C1—S1 | 118.2 (3) | C29—C28—H28 | 119.9 |
C3—C2—C1 | 121.4 (4) | C27—C28—H28 | 119.9 |
C3—C2—H2 | 119.3 | C28—C29—C30 | 120.4 (5) |
C1—C2—H2 | 119.3 | C28—C29—H29 | 119.8 |
C4—C3—C2 | 119.1 (4) | C30—C29—H29 | 119.8 |
C4—C3—H3 | 120.5 | C25—C30—C29 | 120.4 (4) |
C2—C3—H3 | 120.5 | C25—C30—H30 | 119.8 |
C5—C4—C3 | 122.0 (4) | C29—C30—H30 | 119.8 |
C5—C4—F1 | 119.0 (5) | C36—C31—C32 | 118.6 (3) |
C3—C4—F1 | 119.0 (5) | C36—C31—P2 | 119.2 (3) |
C4—C5—C6 | 118.6 (4) | C32—C31—P2 | 121.9 (3) |
C4—C5—H5 | 120.7 | C33—C32—C31 | 120.7 (4) |
C6—C5—H5 | 120.7 | C33—C32—H32 | 119.6 |
C5—C6—C1 | 121.7 (4) | C31—C32—H32 | 119.6 |
C5—C6—H6 | 119.1 | C34—C33—C32 | 119.4 (4) |
C1—C6—H6 | 119.1 | C34—C33—H33 | 120.3 |
C8—C7—C12 | 118.5 (4) | C32—C33—H33 | 120.3 |
C8—C7—P1 | 122.4 (3) | C35—C34—C33 | 121.0 (4) |
C12—C7—P1 | 119.0 (3) | C35—C34—H34 | 119.5 |
C7—C8—C9 | 120.6 (5) | C33—C34—H34 | 119.5 |
C7—C8—H8 | 119.7 | C34—C35—C36 | 119.8 (4) |
C9—C8—H8 | 119.7 | C34—C35—H35 | 120.1 |
C10—C9—C8 | 120.9 (5) | C36—C35—H35 | 120.1 |
C10—C9—H9 | 119.6 | C35—C36—C31 | 120.4 (4) |
C8—C9—H9 | 119.6 | C35—C36—H36 | 119.8 |
C9—C10—C11 | 119.1 (5) | C31—C36—H36 | 119.8 |
C9—C10—H10 | 120.4 | C38—C37—C42 | 117.7 (4) |
C11—C10—H10 | 120.4 | C38—C37—P2 | 120.4 (3) |
C12—C11—C10 | 120.8 (5) | C42—C37—P2 | 121.3 (3) |
C12—C11—H11 | 119.6 | C37—C38—C39 | 121.4 (4) |
C10—C11—H11 | 119.6 | C37—C38—H38 | 119.3 |
C11—C12—C7 | 119.9 (5) | C39—C38—H38 | 119.3 |
C11—C12—H12 | 120.0 | C40—C39—C38 | 119.7 (5) |
C7—C12—H12 | 120.0 | C40—C39—H39 | 120.1 |
C18—C13—C14 | 119.0 (4) | C38—C39—H39 | 120.1 |
C18—C13—P1 | 119.2 (3) | C39—C40—C41 | 120.7 (5) |
C14—C13—P1 | 121.8 (3) | C39—C40—H40 | 119.7 |
C15—C14—C13 | 120.4 (5) | C41—C40—H40 | 119.7 |
C15—C14—H14 | 119.8 | C42—C41—C40 | 119.9 (5) |
C13—C14—H14 | 119.8 | C42—C41—H41 | 120.0 |
C16—C15—C14 | 120.6 (6) | C40—C41—H41 | 120.0 |
C16—C15—H15 | 119.7 | C41—C42—C37 | 120.5 (5) |
C14—C15—H15 | 119.7 | C41—C42—H42 | 119.7 |
C15—C16—C17 | 120.1 (5) | C37—C42—H42 | 119.7 |
C15—C16—H16 | 120.0 | C43—O1—H1 | 115.9 |
C17—C16—H16 | 120.0 | O1—C43—H43A | 109.5 |
C16—C17—C18 | 119.0 (6) | O1—C43—H43B | 109.5 |
C16—C17—H17 | 120.5 | H43A—C43—H43B | 109.5 |
C18—C17—H17 | 120.5 | O1—C43—H43C | 109.5 |
C13—C18—C17 | 120.9 (5) | H43A—C43—H43C | 109.5 |
C13—C18—H18 | 119.6 | H43B—C43—H43C | 109.5 |
C17—C18—H18 | 119.6 | C43B—O1B—H1B | 106.1 |
C24—C19—C20 | 118.1 (4) | O1B—C43B—H43D | 109.5 |
C24—C19—P1 | 121.9 (3) | O1B—C43B—H43E | 109.5 |
C20—C19—P1 | 120.0 (3) | H43D—C43B—H43E | 109.5 |
C19—C20—C21 | 120.9 (5) | O1B—C43B—H43F | 109.5 |
C19—C20—H20 | 119.6 | H43D—C43B—H43F | 109.5 |
C21—C20—H20 | 119.6 | H43E—C43B—H43F | 109.5 |
C22—C21—C20 | 119.0 (5) | ||
Pd1—S1—C1—C2 | −24.8 (4) | C19—C20—C21—C22 | −2.0 (9) |
Pd1—S1—C1—C6 | 158.4 (3) | C20—C21—C22—C23 | 1.5 (11) |
C6—C1—C2—C3 | −1.6 (6) | C21—C22—C23—C24 | −0.1 (12) |
S1—C1—C2—C3 | −178.5 (3) | C20—C19—C24—C23 | 0.4 (8) |
C1—C2—C3—C4 | 1.3 (6) | P1—C19—C24—C23 | −178.6 (5) |
C2—C3—C4—C5 | 0.6 (7) | C22—C23—C24—C19 | −0.9 (10) |
C2—C3—C4—F1 | 179.5 (4) | C37—P2—C25—C26 | 51.5 (4) |
C3—C4—C5—C6 | −1.9 (7) | C31—P2—C25—C26 | 156.9 (3) |
F1—C4—C5—C6 | 179.2 (4) | Pd1—P2—C25—C26 | −79.6 (3) |
C4—C5—C6—C1 | 1.5 (7) | C37—P2—C25—C30 | −135.2 (3) |
C2—C1—C6—C5 | 0.3 (6) | C31—P2—C25—C30 | −29.8 (4) |
S1—C1—C6—C5 | 177.4 (3) | Pd1—P2—C25—C30 | 93.7 (3) |
C13—P1—C7—C8 | −28.2 (4) | C30—C25—C26—C27 | 1.2 (6) |
C19—P1—C7—C8 | −137.7 (3) | P2—C25—C26—C27 | 174.8 (3) |
Pd1—P1—C7—C8 | 101.5 (3) | C25—C26—C27—C28 | −0.2 (7) |
C13—P1—C7—C12 | 154.7 (3) | C26—C27—C28—C29 | −1.5 (8) |
C19—P1—C7—C12 | 45.2 (4) | C27—C28—C29—C30 | 2.1 (8) |
Pd1—P1—C7—C12 | −75.6 (3) | C26—C25—C30—C29 | −0.7 (6) |
C12—C7—C8—C9 | −0.7 (6) | P2—C25—C30—C29 | −174.0 (3) |
P1—C7—C8—C9 | −177.8 (3) | C28—C29—C30—C25 | −1.0 (7) |
C7—C8—C9—C10 | −0.5 (7) | C25—P2—C31—C36 | 147.5 (3) |
C8—C9—C10—C11 | 0.0 (8) | C37—P2—C31—C36 | −103.8 (3) |
C9—C10—C11—C12 | 1.6 (8) | Pd1—P2—C31—C36 | 27.3 (3) |
C10—C11—C12—C7 | −2.8 (7) | C25—P2—C31—C32 | −38.9 (4) |
C8—C7—C12—C11 | 2.3 (6) | C37—P2—C31—C32 | 69.7 (3) |
P1—C7—C12—C11 | 179.5 (4) | Pd1—P2—C31—C32 | −159.1 (3) |
C19—P1—C13—C18 | −171.9 (3) | C36—C31—C32—C33 | −1.3 (6) |
C7—P1—C13—C18 | 80.0 (3) | P2—C31—C32—C33 | −174.9 (3) |
Pd1—P1—C13—C18 | −52.7 (3) | C31—C32—C33—C34 | 1.1 (7) |
C19—P1—C13—C14 | 7.6 (4) | C32—C33—C34—C35 | −0.3 (7) |
C7—P1—C13—C14 | −100.4 (3) | C33—C34—C35—C36 | −0.4 (7) |
Pd1—P1—C13—C14 | 126.8 (3) | C34—C35—C36—C31 | 0.1 (6) |
C18—C13—C14—C15 | 0.4 (7) | C32—C31—C36—C35 | 0.7 (6) |
P1—C13—C14—C15 | −179.1 (4) | P2—C31—C36—C35 | 174.5 (3) |
C13—C14—C15—C16 | −1.5 (8) | C25—P2—C37—C38 | −162.9 (3) |
C14—C15—C16—C17 | 0.4 (9) | C31—P2—C37—C38 | 85.9 (4) |
C15—C16—C17—C18 | 1.6 (8) | Pd1—P2—C37—C38 | −40.0 (4) |
C14—C13—C18—C17 | 1.6 (6) | C25—P2—C37—C42 | 25.5 (4) |
P1—C13—C18—C17 | −178.8 (3) | C31—P2—C37—C42 | −85.7 (4) |
C16—C17—C18—C13 | −2.7 (7) | Pd1—P2—C37—C42 | 148.4 (3) |
C13—P1—C19—C24 | −77.5 (4) | C42—C37—C38—C39 | −0.1 (6) |
C7—P1—C19—C24 | 31.4 (4) | P2—C37—C38—C39 | −172.0 (4) |
Pd1—P1—C19—C24 | 159.5 (4) | C37—C38—C39—C40 | −1.0 (7) |
C13—P1—C19—C20 | 103.6 (4) | C38—C39—C40—C41 | 1.6 (8) |
C7—P1—C19—C20 | −147.6 (4) | C39—C40—C41—C42 | −1.1 (8) |
Pd1—P1—C19—C20 | −19.4 (4) | C40—C41—C42—C37 | 0.0 (8) |
C24—C19—C20—C21 | 1.1 (8) | C38—C37—C42—C41 | 0.6 (7) |
P1—C19—C20—C21 | −179.9 (4) | P2—C37—C42—C41 | 172.4 (4) |
D—H···A | D—H | H···A | D···A | D—H···A |
C34—H34···Cl1i | 0.93 | 2.99 | 3.631 (5) | 127 |
C35—H35···Cl1i | 0.93 | 2.97 | 3.616 (4) | 128 |
Symmetry code: (i) x, y−1, z. |
D—H···A | D—H | H···A | D···A | D—H···A |
C34—H34···Cl1i | 0.93 | 2.99 | 3.631 (5) | 127 |
C35—H35···Cl1i | 0.93 | 2.97 | 3.616 (4) | 128 |
Symmetry code: (i) x, y−1, z. |
Acknowledgements
ESJ thanks PROMEP "Apoyo a perfil deseable". Financial support of this research by CONACYT (grant No. CB2010–154732) and PAPIIT (grant No. IN201711–3) is gratefully acknowledged. RRM and DMM thank Dr Ruben A. Toscano for technical assistance.
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