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Acta Crystallogr Sect E Struct Rep Online. 2010 September 1; 66(Pt 9): m1170–m1171.
Published online 2010 August 28. doi:  10.1107/S160053681003357X
PMCID: PMC3008042

[2-(Diphenyl­phosphan­yl)benzene­thiol­ato-κ2 P,S](pyridine-2-thiol­ato-κS)(triphenyl­phosphine-κP)palladium(II)

Abstract

In the title compound, [Pd(C5H4NS)(C18H14PS)(C18H15P)], the PdII atom has a slightly distorted square-planar environment. Two coordination sites are occupied by a P,S-chelating 2-(diphenyl­phosphan­yl)benzene­thiol­ate ligand and the other two by a P atom from a triphenyl­phosphine ligand and an S atom from a pyridine-2-thiol­ate ligand, exhibiting a trans arrangement of the two P-donor atoms. In the crystal structure, weak intra- and inter­molecular C—H(...)π and π–π inter­actions are observed. The pyridyl ring is equally disordered over two positions.

Related literature

For general background to non-symmetric chelating ligands, see: Braunstein & Naud (2001 [triangle]); Dilworth et al. (2000 [triangle]); Dilworth & Weatley (2000 [triangle]); Serrano-Becerra et al. (2010 [triangle]); Solano-Prado et al. (2010 [triangle]). For a related structure, see: Benefiel et al. (1984 [triangle]). For the synthesis of transition metal complexes with P,S-non-symmetric ligands, see: Canseco-González et al. (2003 [triangle], 2004 [triangle]); Fierro-Arias et al. (2008 [triangle]); Gómez-Benítez et al. (2003 [triangle], 2007a [triangle],b [triangle]); Hernández-Ortega & Morales-Morales (2008 [triangle]); Morales-Morales et al. (2002a [triangle],b [triangle]); Ríos-Moreno et al. (2005 [triangle]).

An external file that holds a picture, illustration, etc.
Object name is e-66-m1170-scheme1.jpg

Experimental

Crystal data

  • [Pd(C5H4NS)(C18H14PS)(C18H15P)]
  • M r = 772.14
  • Triclinic, An external file that holds a picture, illustration, etc.
Object name is e-66-m1170-efi1.jpg
  • a = 11.399 (5) Å
  • b = 12.178 (5) Å
  • c = 13.467 (5) Å
  • α = 83.623 (5)°
  • β = 76.379 (5)°
  • γ = 75.135 (5)°
  • V = 1753.5 (12) Å3
  • Z = 2
  • Mo Kα radiation
  • μ = 0.77 mm−1
  • T = 298 K
  • 0.34 × 0.06 × 0.05 mm

Data collection

  • Bruker SMART APEX CCD diffractometer
  • Absorption correction: multi-scan (SADABS; Bruker, 2001 [triangle]) T min = 0.780, T max = 0.963
  • 14855 measured reflections
  • 6429 independent reflections
  • 4588 reflections with I > 2σ(I)
  • R int = 0.046

Refinement

  • R[F 2 > 2σ(F 2)] = 0.053
  • wR(F 2) = 0.123
  • S = 1.02
  • 6429 reflections
  • 470 parameters
  • 186 restraints
  • H-atom parameters constrained
  • Δρmax = 0.71 e Å−3
  • Δρmin = −0.30 e Å−3

Data collection: SMART (Bruker, 2007 [triangle]); cell refinement: SAINT-Plus (Bruker, 2007 [triangle]); data reduction: SAINT-Plus; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 [triangle]); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 [triangle]); molecular graphics: SHELXTL (Sheldrick, 2008 [triangle]); software used to prepare material for publication: SHELXTL.

Table 1
Selected bond lengths (Å)
Table 2
Intra- and inter­molecular C—H(...)π and π–π inter­actions (Å)

Supplementary Material

Crystal structure: contains datablocks I, global. DOI: 10.1107/S160053681003357X/hy2339sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S160053681003357X/hy2339Isup2.hkl

Additional supplementary materials: crystallographic information; 3D view; checkCIF report

Acknowledgments

The support of this research by CONACYT (F58692) and DGAPA-UNAM (IN227008) is gratefully acknowledged.

supplementary crystallographic information

Comment

Nonsymmetric chelating ligands have had a renaissance in recent years due to the potential properties they may confer to the compounds they form (Dilworth & Weatley, 2000). Thus, steric and electronic effects can be modified easily due in part to the pronounced chemical differences among the donor atoms in these ligands (Serrano-Becerra et al., 2010; Solano-Prado et al., 2010). Properties such as hemilability (Braunstein & Naud, 2001) have been invoked to explain the often observed enhanced reactivities of these metallic complexes, turning these species very attractive for their potential applications in homogeneous catalysis and metal mediated organic synthesis (Dilworth et al., 2000). Thus, given our continuous interest in the synthesis of transition metal complexes bearing P,S-nonsymmetric hybrid ligands (Canseco-González et al., 2003, 2004; Fierro-Arias et al., 2008; Gómez-Benítez et al., 2003, 2007a,b; Hernández-Ortega & Morales-Morales, 2008; Morales-Morales et al., 2002a,b; Ríos-Moreno et al., 2005), we report here the structure of the title complex.

The title palladium complex (Fig. 1) consists of a diphenylphosphinobenzenethiolate ligand coordinated in a bidentated manner, a triphenylphosphine ligand arranged in a trans configuration with respect to the P atom of the P,S-chelating ligand and a pyridin-2-thiolate ligand coordinated by the S atom. The Pd—S distances observed are different (0.04 Å) (Table 1), while the Pd—P distance in the triphenylphosphine ligand are slightly longer than that observed in the diphenylphosphine fragment of the P,S-ligand (0.1 Å), due to the preferred bite angle of the chelate ligand. The disordered pyridyl ring of the pyridin-2-thiolate ligand and the phenyl rings (C7–C12 and C19–C24) exhibits important intramolecular face–to–face π–π interactions [centroid–centroid distances = 4.00 (2) and 3.93 (2) Å]. Additionally, the crystal packing is also supported by intermolecular C—H···π and π–π interactions (Table 2).

Experimental

The title compound was synthesized from the metathetical reaction of triphenylphosphine-2-(diphenylphosphine)benzenethiolate palladium(II) chloride [κ2-(SC6H4-2-PPh2)Pd(PPh3)Cl] (100 mg, 143 mmol) with lead 2-mercaptopirydine [Pb(C5H4N-2-S)2] (31 mg, 72 mmol) in a 2:1 molar ratio. The title compound was obtained as a bright yellow microcrystalline powder in a 92% (101 mg) yield.

Refinement

H atoms were positioned geometrically and refined as riding atoms, with C—H = 0.93Å and with Uiso(H) = 1.2Ueq(C). The pyridyl ring is disordered and was refined in two positions each with an occupancy factor of 0.50 (2).

Figures

Fig. 1.
The molecular structure of the title compound. Displacement ellipsoids are drawn at the 40% probability level. Only the H atoms involved in C—H···π interactions are shown. Dashed lines denote C—H···π ...

Crystal data

[Pd(C5H4NS)(C18H14PS)(C18H15P)]Z = 2
Mr = 772.14F(000) = 788
Triclinic, P1Dx = 1.462 Mg m3
Hall symbol: -P 1Mo Kα radiation, λ = 0.71069 Å
a = 11.399 (5) ÅCell parameters from 3920 reflections
b = 12.178 (5) Åθ = 2.2–24.6°
c = 13.467 (5) ŵ = 0.77 mm1
α = 83.623 (5)°T = 298 K
β = 76.379 (5)°Prism, yellow
γ = 75.135 (5)°0.34 × 0.06 × 0.05 mm
V = 1753.5 (12) Å3

Data collection

Bruker SMART APEX CCD diffractometer6429 independent reflections
Radiation source: fine-focus sealed tube4588 reflections with I > 2σ(I)
graphiteRint = 0.046
[var phi] and ω scansθmax = 25.4°, θmin = 1.6°
Absorption correction: multi-scan (SADABS; Bruker, 2001)h = −13→13
Tmin = 0.780, Tmax = 0.963k = −14→14
14855 measured reflectionsl = −16→16

Refinement

Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.053Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.123H-atom parameters constrained
S = 1.02w = 1/[σ2(Fo2) + (0.0518P)2 + 0.5024P] where P = (Fo2 + 2Fc2)/3
6429 reflections(Δ/σ)max = 0.038
470 parametersΔρmax = 0.71 e Å3
186 restraintsΔρmin = −0.30 e Å3

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2)

xyzUiso*/UeqOcc. (<1)
Pd10.26508 (3)0.20691 (3)0.25871 (3)0.03896 (13)
S10.41538 (12)0.10047 (11)0.34128 (10)0.0527 (3)
S20.10300 (12)0.29994 (11)0.17836 (10)0.0513 (3)
P10.21862 (11)0.04240 (10)0.23856 (9)0.0383 (3)
P20.31291 (12)0.37713 (11)0.28524 (10)0.0435 (3)
C10.3252 (4)−0.0722 (4)0.2934 (3)0.0416 (11)
C20.4067 (4)−0.0419 (4)0.3403 (4)0.0442 (12)
C30.4853 (5)−0.1262 (5)0.3891 (4)0.0609 (15)
H30.5392−0.10680.42250.073*
C40.4824 (6)−0.2371 (5)0.3874 (5)0.0697 (17)
H40.5348−0.29300.42030.084*
C50.4042 (5)−0.2682 (5)0.3384 (5)0.0681 (16)
H50.4050−0.34460.33700.082*
C60.3249 (5)−0.1864 (4)0.2916 (4)0.0546 (13)
H60.2711−0.20690.25880.065*
C70.2388 (4)0.0109 (4)0.1058 (3)0.0400 (11)
C80.3553 (5)−0.0422 (4)0.0520 (4)0.0492 (12)
H80.4197−0.06980.08640.059*
C90.3772 (5)−0.0547 (5)−0.0516 (4)0.0603 (15)
H90.4561−0.0902−0.08680.072*
C100.2838 (7)−0.0154 (5)−0.1027 (4)0.0710 (17)
H100.2990−0.0233−0.17270.085*
C110.1676 (6)0.0357 (5)−0.0511 (4)0.0708 (17)
H110.10330.0606−0.08590.085*
C120.1447 (5)0.0509 (4)0.0533 (4)0.0529 (13)
H120.06600.08800.08760.063*
C130.0628 (4)0.0290 (4)0.3020 (3)0.0449 (12)
C140.0115 (5)−0.0538 (5)0.2790 (4)0.0682 (16)
H140.0556−0.10310.22760.082*
C15−0.1055 (6)−0.0635 (6)0.3322 (5)0.083 (2)
H15−0.1394−0.11940.31630.100*
C16−0.1711 (6)0.0075 (6)0.4073 (5)0.0814 (19)
H16−0.24940.00010.44280.098*
C17−0.1224 (5)0.0892 (5)0.4307 (5)0.0714 (17)
H17−0.16750.13810.48200.086*
C18−0.0057 (5)0.0999 (4)0.3782 (4)0.0556 (13)
H180.02700.15620.39490.067*
C190.2835 (5)0.5004 (4)0.1960 (4)0.0511 (13)
C200.1634 (6)0.5559 (5)0.1907 (5)0.0710 (17)
H200.09850.52800.23200.085*
C210.1352 (7)0.6508 (5)0.1270 (6)0.084 (2)
H210.05300.68780.12680.101*
C220.2296 (8)0.6888 (6)0.0650 (5)0.089 (2)
H220.21240.75350.02220.107*
C230.3497 (8)0.6337 (6)0.0642 (5)0.093 (2)
H230.41360.65940.01900.111*
C240.3780 (6)0.5397 (5)0.1301 (4)0.0683 (16)
H240.46040.50330.12980.082*
C250.4744 (4)0.3612 (4)0.2925 (4)0.0440 (11)
C260.5669 (5)0.2975 (5)0.2206 (4)0.0632 (15)
H260.54610.26210.17170.076*
C270.6903 (6)0.2867 (5)0.2217 (5)0.0710 (17)
H270.75210.24470.17260.085*
C280.7229 (5)0.3366 (5)0.2934 (5)0.0685 (16)
H280.80620.32830.29390.082*
C290.6308 (5)0.3994 (5)0.3650 (4)0.0653 (15)
H290.65210.43440.41390.078*
C300.5090 (5)0.4110 (4)0.3649 (4)0.0490 (12)
H300.44800.45300.41450.059*
C310.2270 (4)0.4299 (4)0.4100 (4)0.0460 (12)
C320.2156 (5)0.3516 (5)0.4923 (4)0.0588 (14)
H320.24600.27420.48240.071*
C330.1589 (6)0.3888 (6)0.5892 (5)0.0779 (19)
H330.15390.33620.64470.093*
C340.1106 (5)0.5011 (7)0.6040 (5)0.078 (2)
H340.07130.52500.66940.093*
C350.1194 (5)0.5791 (6)0.5236 (6)0.0740 (18)
H350.08550.65600.53390.089*
C360.1780 (5)0.5440 (5)0.4277 (4)0.0572 (14)
H360.18520.59780.37330.069*
C380.1818 (5)0.3228 (4)0.0538 (4)0.0555 (12)
N370.3081 (7)0.2875 (18)0.0324 (10)0.068 (3)0.50 (2)
C390.1267 (10)0.4052 (14)−0.0117 (8)0.064 (3)0.50 (2)
H390.04480.44520.01010.077*0.50 (2)
C400.1895 (14)0.4282 (14)−0.1058 (8)0.071 (3)0.50 (2)
H400.14990.4812−0.14990.086*0.50 (2)
C410.3102 (14)0.3744 (16)−0.1364 (9)0.076 (3)0.50 (2)
H410.35250.3819−0.20400.092*0.50 (2)
C420.3674 (10)0.3094 (16)−0.0654 (11)0.077 (3)0.50 (2)
H420.45230.2777−0.08450.092*0.50 (2)
N37A0.3023 (8)0.2694 (18)0.0152 (9)0.067 (3)0.50 (2)
C39A0.1072 (10)0.3708 (15)−0.0149 (7)0.064 (3)0.50 (2)
H39A0.02130.39060.00820.077*0.50 (2)
C40A0.1566 (14)0.3893 (16)−0.1138 (7)0.073 (3)0.50 (2)
H40A0.10530.4265−0.15770.088*0.50 (2)
C41A0.2798 (14)0.3544 (16)−0.1503 (8)0.077 (3)0.50 (2)
H41A0.31650.3743−0.21690.092*0.50 (2)
C42A0.3480 (11)0.2893 (16)−0.0863 (9)0.072 (3)0.50 (2)
H42A0.43110.2562−0.11310.086*0.50 (2)

Atomic displacement parameters (Å2)

U11U22U33U12U13U23
Pd10.0445 (2)0.0354 (2)0.0403 (2)−0.01175 (16)−0.01242 (16)−0.00360 (15)
S10.0589 (8)0.0490 (8)0.0591 (8)−0.0123 (7)−0.0298 (7)−0.0047 (6)
S20.0449 (8)0.0520 (8)0.0570 (8)−0.0081 (6)−0.0146 (6)−0.0037 (6)
P10.0431 (7)0.0367 (7)0.0380 (7)−0.0127 (6)−0.0100 (5)−0.0038 (5)
P20.0466 (8)0.0403 (7)0.0475 (8)−0.0142 (6)−0.0124 (6)−0.0046 (6)
C10.043 (3)0.043 (3)0.037 (3)−0.012 (2)−0.003 (2)−0.001 (2)
C20.046 (3)0.042 (3)0.043 (3)−0.007 (2)−0.010 (2)0.000 (2)
C30.063 (4)0.061 (4)0.063 (4)−0.014 (3)−0.026 (3)0.002 (3)
C40.070 (4)0.051 (4)0.079 (4)−0.003 (3)−0.023 (3)0.020 (3)
C50.073 (4)0.037 (3)0.092 (5)−0.011 (3)−0.024 (4)0.015 (3)
C60.061 (3)0.042 (3)0.064 (3)−0.019 (3)−0.017 (3)0.003 (3)
C70.045 (3)0.038 (3)0.039 (3)−0.018 (2)−0.006 (2)−0.003 (2)
C80.054 (3)0.048 (3)0.048 (3)−0.017 (3)−0.008 (2)−0.005 (2)
C90.061 (4)0.065 (4)0.052 (3)−0.024 (3)0.011 (3)−0.019 (3)
C100.100 (5)0.080 (4)0.039 (3)−0.035 (4)−0.009 (3)−0.012 (3)
C110.094 (5)0.080 (4)0.048 (3)−0.028 (4)−0.027 (3)−0.002 (3)
C120.053 (3)0.059 (3)0.051 (3)−0.015 (3)−0.014 (3)−0.011 (3)
C130.048 (3)0.048 (3)0.039 (3)−0.014 (2)−0.008 (2)0.000 (2)
C140.072 (4)0.076 (4)0.064 (4)−0.039 (3)−0.006 (3)−0.006 (3)
C150.076 (5)0.101 (5)0.085 (5)−0.054 (4)−0.006 (4)−0.002 (4)
C160.055 (4)0.103 (5)0.081 (5)−0.031 (4)0.003 (3)0.007 (4)
C170.058 (4)0.076 (4)0.064 (4)−0.008 (3)0.007 (3)0.001 (3)
C180.057 (3)0.051 (3)0.056 (3)−0.010 (3)−0.010 (3)−0.004 (3)
C190.073 (4)0.042 (3)0.046 (3)−0.020 (3)−0.020 (3)−0.005 (2)
C200.068 (4)0.055 (4)0.094 (5)−0.021 (3)−0.028 (4)0.012 (3)
C210.100 (5)0.056 (4)0.106 (6)−0.015 (4)−0.054 (5)0.011 (4)
C220.136 (7)0.056 (4)0.072 (5)−0.014 (5)−0.030 (5)0.006 (3)
C230.124 (7)0.072 (5)0.071 (5)−0.033 (5)0.002 (4)0.012 (4)
C240.076 (4)0.059 (4)0.061 (4)−0.011 (3)−0.005 (3)−0.001 (3)
C250.044 (3)0.037 (3)0.052 (3)−0.013 (2)−0.010 (2)0.003 (2)
C260.056 (4)0.074 (4)0.064 (4)−0.021 (3)−0.008 (3)−0.024 (3)
C270.058 (4)0.071 (4)0.074 (4)−0.014 (3)0.006 (3)−0.013 (3)
C280.054 (4)0.072 (4)0.084 (4)−0.016 (3)−0.025 (3)0.001 (4)
C290.056 (4)0.083 (4)0.067 (4)−0.023 (3)−0.022 (3)−0.012 (3)
C300.049 (3)0.054 (3)0.046 (3)−0.014 (3)−0.012 (2)−0.006 (2)
C310.039 (3)0.044 (3)0.058 (3)−0.011 (2)−0.010 (2)−0.011 (3)
C320.063 (4)0.053 (3)0.055 (3)−0.016 (3)−0.001 (3)−0.004 (3)
C330.092 (5)0.088 (5)0.055 (4)−0.035 (4)0.001 (3)−0.016 (3)
C340.057 (4)0.105 (6)0.076 (5)−0.032 (4)0.008 (3)−0.044 (4)
C350.064 (4)0.060 (4)0.100 (5)−0.014 (3)−0.006 (4)−0.040 (4)
C360.054 (3)0.054 (3)0.069 (4)−0.017 (3)−0.012 (3)−0.015 (3)
C380.053 (2)0.056 (3)0.063 (3)−0.012 (2)−0.024 (2)−0.001 (2)
N370.056 (3)0.068 (6)0.080 (4)−0.014 (4)−0.015 (3)0.005 (4)
C390.055 (4)0.077 (6)0.060 (4)−0.011 (4)−0.021 (3)0.003 (4)
C400.066 (5)0.089 (6)0.063 (4)−0.019 (4)−0.025 (4)0.008 (4)
C410.066 (5)0.092 (6)0.071 (4)−0.022 (4)−0.012 (4)0.001 (4)
C420.061 (4)0.078 (6)0.082 (5)−0.011 (4)−0.008 (3)0.003 (5)
N37A0.054 (3)0.067 (6)0.081 (4)−0.017 (4)−0.018 (3)0.007 (5)
C39A0.055 (4)0.077 (6)0.060 (4)−0.013 (4)−0.022 (3)0.007 (4)
C40A0.064 (4)0.091 (6)0.066 (3)−0.018 (4)−0.024 (4)0.010 (4)
C41A0.067 (5)0.091 (6)0.070 (4)−0.020 (5)−0.014 (4)0.003 (4)
C42A0.055 (4)0.077 (6)0.081 (4)−0.016 (4)−0.012 (3)0.001 (5)

Geometric parameters (Å, °)

Pd1—P12.2585 (15)C21—H210.9300
Pd1—P22.3575 (15)C22—C231.359 (9)
Pd1—S12.2999 (15)C22—H220.9300
Pd1—S22.3374 (15)C23—C241.387 (8)
S1—C21.764 (5)C23—H230.9300
S2—C381.735 (6)C24—H240.9300
P1—C11.815 (5)C25—C301.382 (6)
P1—C71.819 (5)C25—C261.384 (7)
P1—C131.821 (5)C26—C271.382 (8)
P2—C251.826 (5)C26—H260.9300
P2—C311.827 (5)C27—C281.362 (8)
P2—C191.828 (5)C27—H270.9300
C1—C21.380 (6)C28—C291.375 (8)
C1—C61.394 (6)C28—H280.9300
C2—C31.394 (7)C29—C301.359 (7)
C3—C41.362 (8)C29—H290.9300
C3—H30.9300C30—H300.9300
C4—C51.371 (8)C31—C361.383 (7)
C4—H40.9300C31—C321.384 (7)
C5—C61.368 (7)C32—C331.382 (7)
C5—H50.9300C32—H320.9300
C6—H60.9300C33—C341.355 (9)
C7—C121.379 (6)C33—H330.9300
C7—C81.384 (6)C34—C351.362 (9)
C8—C91.378 (7)C34—H340.9300
C8—H80.9300C35—C361.366 (8)
C9—C101.358 (8)C35—H350.9300
C9—H90.9300C36—H360.9300
C10—C111.365 (8)C38—N371.362 (8)
C10—H100.9300C38—N37A1.365 (8)
C11—C121.393 (7)C38—C39A1.384 (9)
C11—H110.9300C38—C391.385 (9)
C12—H120.9300N37—C421.363 (9)
C13—C181.372 (7)C39—C401.339 (10)
C13—C141.383 (7)C39—H390.9300
C14—C151.385 (8)C40—C411.351 (10)
C14—H140.9300C40—H400.9300
C15—C161.355 (9)C41—C421.351 (11)
C15—H150.9300C41—H410.9300
C16—C171.353 (9)C42—H420.9300
C16—H160.9300N37A—C42A1.362 (9)
C17—C181.383 (7)C39A—C40A1.336 (10)
C17—H170.9300C39A—H39A0.9300
C18—H180.9300C40A—C41A1.346 (10)
C19—C241.377 (7)C40A—H40A0.9300
C19—C201.377 (7)C41A—C42A1.350 (11)
C20—C211.376 (8)C41A—H41A0.9300
C20—H200.9300C42A—H42A0.9300
C21—C221.348 (9)
P1—Pd1—S187.50 (5)C22—C21—H21120.8
P1—Pd1—S287.20 (5)C20—C21—H21120.8
S1—Pd1—S2174.33 (5)C21—C22—C23120.8 (7)
P1—Pd1—P2178.22 (5)C21—C22—H22119.6
S1—Pd1—P291.42 (5)C23—C22—H22119.6
S2—Pd1—P293.83 (5)C22—C23—C24120.7 (7)
C2—S1—Pd1105.60 (16)C22—C23—H23119.6
C38—S2—Pd1102.20 (18)C24—C23—H23119.6
C1—P1—C7106.4 (2)C19—C24—C23119.7 (6)
C1—P1—C13106.3 (2)C19—C24—H24120.1
C7—P1—C13106.1 (2)C23—C24—H24120.1
C1—P1—Pd1107.42 (16)C30—C25—C26118.4 (5)
C7—P1—Pd1114.19 (15)C30—C25—P2123.4 (4)
C13—P1—Pd1115.84 (16)C26—C25—P2118.2 (4)
C25—P2—C31102.7 (2)C27—C26—C25119.8 (5)
C25—P2—C19103.6 (2)C27—C26—H26120.1
C31—P2—C19104.2 (2)C25—C26—H26120.1
C25—P2—Pd1114.30 (16)C28—C27—C26121.1 (6)
C31—P2—Pd1110.55 (16)C28—C27—H27119.5
C19—P2—Pd1119.64 (16)C26—C27—H27119.5
C2—C1—C6120.2 (4)C27—C28—C29119.0 (5)
C2—C1—P1117.0 (4)C27—C28—H28120.5
C6—C1—P1122.8 (4)C29—C28—H28120.5
C1—C2—C3119.3 (5)C30—C29—C28120.7 (5)
C1—C2—S1122.4 (4)C30—C29—H29119.6
C3—C2—S1118.3 (4)C28—C29—H29119.6
C4—C3—C2119.5 (5)C29—C30—C25121.0 (5)
C4—C3—H3120.3C29—C30—H30119.5
C2—C3—H3120.3C25—C30—H30119.5
C3—C4—C5121.6 (5)C36—C31—C32118.3 (5)
C3—C4—H4119.2C36—C31—P2123.6 (4)
C5—C4—H4119.2C32—C31—P2118.1 (4)
C6—C5—C4119.7 (5)C33—C32—C31119.8 (5)
C6—C5—H5120.1C33—C32—H32120.1
C4—C5—H5120.1C31—C32—H32120.1
C5—C6—C1119.7 (5)C34—C33—C32120.6 (6)
C5—C6—H6120.1C34—C33—H33119.7
C1—C6—H6120.1C32—C33—H33119.7
C12—C7—C8118.5 (4)C33—C34—C35120.3 (6)
C12—C7—P1121.5 (4)C33—C34—H34119.9
C8—C7—P1119.5 (4)C35—C34—H34119.9
C9—C8—C7121.0 (5)C34—C35—C36119.9 (6)
C9—C8—H8119.5C34—C35—H35120.1
C7—C8—H8119.5C36—C35—H35120.1
C10—C9—C8120.1 (5)C35—C36—C31121.2 (6)
C10—C9—H9119.9C35—C36—H36119.4
C8—C9—H9119.9C31—C36—H36119.4
C9—C10—C11120.0 (5)N37—C38—C39A126.8 (8)
C9—C10—H10120.0N37A—C38—C39A117.8 (7)
C11—C10—H10120.0N37—C38—C39118.1 (7)
C10—C11—C12120.4 (6)N37A—C38—C39115.0 (8)
C10—C11—H11119.8N37—C38—S2117.8 (6)
C12—C11—H11119.8N37A—C38—S2124.1 (5)
C7—C12—C11119.9 (5)C39A—C38—S2115.3 (6)
C7—C12—H12120.0C39—C38—S2120.7 (6)
C11—C12—H12120.0C38—N37—C42116.3 (7)
C18—C13—C14118.0 (5)C40—C39—C38121.1 (8)
C18—C13—P1119.7 (4)C40—C39—H39119.4
C14—C13—P1122.3 (4)C38—C39—H39119.4
C13—C14—C15120.1 (6)C39—C40—C41119.9 (8)
C13—C14—H14119.9C39—C40—H40120.1
C15—C14—H14119.9C41—C40—H40120.0
C16—C15—C14120.7 (6)C42—C41—C40117.6 (8)
C16—C15—H15119.6C42—C41—H41121.2
C14—C15—H15119.6C40—C41—H41121.2
C17—C16—C15119.9 (6)C41—C42—N37124.0 (8)
C17—C16—H16120.0C41—C42—H42118.0
C15—C16—H16120.0N37—C42—H42118.0
C16—C17—C18120.0 (6)C42A—N37A—C38117.1 (7)
C16—C17—H17120.0C40A—C39A—C38121.1 (8)
C18—C17—H17120.0C40A—C39A—H39A119.5
C13—C18—C17121.2 (5)C38—C39A—H39A119.5
C13—C18—H18119.4C39A—C40A—C41A120.6 (8)
C17—C18—H18119.4C39A—C40A—H40A119.7
C24—C19—C20117.4 (5)C41A—C40A—H40A119.7
C24—C19—P2122.5 (4)C40A—C41A—C42A117.3 (8)
C20—C19—P2120.1 (4)C40A—C41A—H41A121.4
C21—C20—C19122.8 (6)C42A—C41A—H41A121.4
C21—C20—H20118.6C41A—C42A—N37A123.9 (8)
C19—C20—H20118.6C41A—C42A—H42A118.1
C22—C21—C20118.4 (7)N37A—C42A—H42A118.1
P1—Pd1—S1—C20.08 (17)C31—P2—C19—C20−56.4 (5)
P2—Pd1—S1—C2178.66 (17)Pd1—P2—C19—C2067.8 (5)
P1—Pd1—S2—C38−99.05 (19)C24—C19—C20—C21−3.4 (9)
P2—Pd1—S2—C3882.41 (19)P2—C19—C20—C21178.3 (5)
S1—Pd1—P1—C1−1.59 (15)C19—C20—C21—C222.1 (10)
S2—Pd1—P1—C1−179.60 (15)C20—C21—C22—C231.0 (11)
S1—Pd1—P1—C7−119.32 (18)C21—C22—C23—C24−2.5 (11)
S2—Pd1—P1—C762.67 (17)C20—C19—C24—C231.8 (8)
S1—Pd1—P1—C13116.98 (18)P2—C19—C24—C23−179.9 (5)
S2—Pd1—P1—C13−61.03 (18)C22—C23—C24—C191.1 (10)
S1—Pd1—P2—C2529.13 (18)C31—P2—C25—C30−16.2 (5)
S2—Pd1—P2—C25−153.00 (18)C19—P2—C25—C3092.1 (4)
S1—Pd1—P2—C31−86.20 (18)Pd1—P2—C25—C30−136.0 (4)
S2—Pd1—P2—C3191.67 (18)C31—P2—C25—C26164.9 (4)
S1—Pd1—P2—C19152.8 (2)C19—P2—C25—C26−86.8 (4)
S2—Pd1—P2—C19−29.3 (2)Pd1—P2—C25—C2645.1 (4)
C7—P1—C1—C2126.1 (4)C30—C25—C26—C27−1.1 (8)
C13—P1—C1—C2−121.2 (4)P2—C25—C26—C27177.9 (4)
Pd1—P1—C1—C23.4 (4)C25—C26—C27—C280.9 (9)
C7—P1—C1—C6−55.5 (4)C26—C27—C28—C29−0.6 (10)
C13—P1—C1—C657.2 (4)C27—C28—C29—C300.5 (9)
Pd1—P1—C1—C6−178.2 (4)C28—C29—C30—C25−0.8 (9)
C6—C1—C2—C3−2.4 (7)C26—C25—C30—C291.0 (8)
P1—C1—C2—C3176.1 (4)P2—C25—C30—C29−177.9 (4)
C6—C1—C2—S1177.7 (4)C25—P2—C31—C3695.0 (5)
P1—C1—C2—S1−3.8 (5)C19—P2—C31—C36−12.8 (5)
Pd1—S1—C2—C12.2 (4)Pd1—P2—C31—C36−142.6 (4)
Pd1—S1—C2—C3−177.7 (4)C25—P2—C31—C32−81.7 (4)
C1—C2—C3—C41.6 (8)C19—P2—C31—C32170.5 (4)
S1—C2—C3—C4−178.5 (4)Pd1—P2—C31—C3240.7 (4)
C2—C3—C4—C50.2 (9)C36—C31—C32—C33−1.4 (8)
C3—C4—C5—C6−1.3 (9)P2—C31—C32—C33175.5 (4)
C4—C5—C6—C10.6 (9)C31—C32—C33—C342.2 (9)
C2—C1—C6—C51.3 (8)C32—C33—C34—C35−1.2 (10)
P1—C1—C6—C5−177.1 (4)C33—C34—C35—C36−0.6 (9)
C1—P1—C7—C12154.0 (4)C34—C35—C36—C311.3 (9)
C13—P1—C7—C1241.1 (5)C32—C31—C36—C35−0.3 (8)
Pd1—P1—C7—C12−87.7 (4)P2—C31—C36—C35−177.0 (4)
C1—P1—C7—C8−34.1 (4)Pd1—S2—C38—N37−1.2 (12)
C13—P1—C7—C8−147.0 (4)Pd1—S2—C38—N37A15.2 (13)
Pd1—P1—C7—C884.2 (4)Pd1—S2—C38—C39A175.7 (9)
C12—C7—C8—C90.1 (7)Pd1—S2—C38—C39−159.9 (10)
P1—C7—C8—C9−172.0 (4)N37A—C38—N37—C4264 (3)
C7—C8—C9—C10−0.4 (8)C39A—C38—N37—C425(3)
C8—C9—C10—C11−0.6 (9)C39—C38—N37—C42−19 (2)
C9—C10—C11—C121.8 (9)S2—C38—N37—C42−178.3 (12)
C8—C7—C12—C111.0 (7)N37—C38—C39—C4017 (2)
P1—C7—C12—C11173.0 (4)N37A—C38—C39—C400(2)
C10—C11—C12—C7−2.1 (9)C39A—C38—C39—C40−102 (2)
C1—P1—C13—C18102.0 (4)S2—C38—C39—C40175.9 (10)
C7—P1—C13—C18−145.1 (4)C38—C39—C40—C41−3(2)
Pd1—P1—C13—C18−17.2 (5)C39—C40—C41—C42−8(2)
C1—P1—C13—C14−75.3 (5)C40—C41—C42—N376(2)
C7—P1—C13—C1437.6 (5)C38—N37—C42—C418(3)
Pd1—P1—C13—C14165.5 (4)N37—C38—N37A—C42A−115 (5)
C18—C13—C14—C150.0 (8)C39A—C38—N37A—C42A15 (2)
P1—C13—C14—C15177.4 (5)C39—C38—N37A—C42A−10 (2)
C13—C14—C15—C16−0.1 (10)S2—C38—N37A—C42A174.8 (11)
C14—C15—C16—C170.2 (11)N37—C38—C39A—C40A−1(2)
C15—C16—C17—C18−0.2 (10)N37A—C38—C39A—C40A−16 (2)
C14—C13—C18—C170.0 (8)C39—C38—C39A—C40A72.5 (19)
P1—C13—C18—C17−177.4 (4)S2—C38—C39A—C40A−177.8 (10)
C16—C17—C18—C130.1 (9)C38—C39A—C40A—C41A5(2)
C25—P2—C19—C2418.2 (5)C39A—C40A—C41A—C42A8(2)
C31—P2—C19—C24125.4 (5)C40A—C41A—C42A—N37A−9(2)
Pd1—P2—C19—C24−110.5 (4)C38—N37A—C42A—C41A−3(3)
C25—P2—C19—C20−163.6 (4)

Table 2 Intra- and intermolecular C—H···π and π–π interactions (Å)

H/centroidcentroiddistance
N37,C38–C42C19–C243.93 (2)
N37A,C38,C39A–C42AC7–C124.00 (2)
C31–C36C31i–C36i3.76 (2)
H24C25–C303.17
H30C31–C363.11
H36C19–C243.20
H29C31ii–C36ii3.06

Symmetry codes: (i) -x, -y+1, -z+1; (ii) -x+1, -y+1, -z+1.

Footnotes

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: HY2339).

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