supplementary materials


hg5318 scheme

Acta Cryst. (2013). E69, m360-m361    [ doi:10.1107/S1600536813014712 ]

Bis{[2,2'-(5,8,11-trithia-2,14-diazapentadeca-1,14-diene-1,15-diyl)diphenolato]palladium(II)} acetonitrile monosolvate

L. N. Dawe, B. Adhikary, J. L. Collins and C. R. Lucas

Abstract top

The asymmetric unit of the title compound, [Pd(C22H26N2O2S3)]2·CH3CN, contains two complex molecules and a single uncoordinated lattice acetonitrile solvent molecule. The PdII cations have a trans-N2O2 square-planar geometry and the superposition of the two crystallographically independent PdII complexes yields an overall r.m.s. deviation of 0.292 Å. The Pd...Pd separation in the asymmetric unit is 3.3776 (3) Å, while the PdN2O2 plane-plane fold angle is 1.62 (7)°. A short intermolecular S...S contact between the central S atom of one complex and its inversion-related symmetry equivalent of 3.663 (2) Å is observed. Part of the ligand chain (S-C-C-S) in each complex molecule is disordered over two orientations and refined occupancies that converged to 0.450 (10) and 0.550 (10) for the one complex molecule, and 0.789 (9) and 0.211 (9) for the other.

Comment top

The Pd coordination sphere in complexes containing salicylaldimine (sal) ligands significantly affects the catalytic properties of the compounds (Jin et al., 2010). In particular, the tunability of the steric and electronic composition at the metal centre greatly influences catalytic performance.The heptadentate ligand present in the title complex has three different donor types, O, N and S, however, only the phenoxy O atoms and imine N atoms coordinate to the PdII cation, yielding a trans-N2O2 square planar geometry and two six-membered chelate rings. A search in the Cambridge Structural Database (CSD) v. 5.34 with Feb. 2013 update (Allen, 2002) for Pd complexes with molecules containing the noted three possible donor types (with coordination to no other elements allowed) yielded a total of 284 structures, wherein Pd was coordinated to just O and N donors in only 44 structures (and in order of decreasing frequency, the other structures had N & S = 99; only S = 53; O, N & S = 36; only N = 28; O & S = 24; and no examples where oxygen was the only donor.) Given the frequency in which S-coordination appears, it may be that it was not present as a donor in this structure due to the rigid framework established by the sal groups leading to pre-organization of the ligand for preferential coordination and formation of the six-membered chelate rings. A previously reported dinuclear Cu(II) complex containing the same ligand as the title complex, bis(µ2-2,2'-(5,8,11-trithia-2,14-diazapentadeca-1,14-diene-1,15-diyl)diphenolato)-di-copper(II), also exhibits coordination via only the phenoxy O atoms and imine N atoms, however, each copper site is square pyramidal, with axial coordination to a single phenoxy µ2-O donor found in the plane of the second copper (Lucas et al., 2011b).

The asymmetric unit of the title complex contains two metal complex formula units (Z' = 2) and a single uncoordinated lattice solvent molecule of acetonitrile (Figure 1.) Part of the ligand chain (S—C—C—S) in each complex was disordered with two orientations, and refined occupancies that converged to 0.450 (10) and 0.550 (10) for the complex containing Pd1 (S2—C12—C13—S3 and S2A—C12A—C13A—S3A), and 0.789 (9) and 0.211 (9) for the complex containing Pd2 (S5—C34—C35—S6 and S5A—C34A—C35A—S6A.)

The two Pd-containing molecules in the asymmetric unit were overlayed (Figure 2; H-atoms omitted from this analysis), using OLEX2 (Dolomanov et al., 2009), giving an overall root-mean-square deviation of 0.292 Å. In this context, a comparison of the PdN2O2 mean planes to the terminal aromatic ring planes revealed significant deviations from planarity for the molecule containing Pd2 (plane-plane fold angles of 12.69 (8)° and 5.42 (9)° to the rings C23—C28 and C39—C44, respectively) compared with the near planar arrangement for the molecule containing Pd1 (1.19 (9)° and 4.32 (9)° to C1—C6 and C17—C22, respectively.)

While PdII is normally expected to exhibit a stable square planar geometry (16-electron rule), the presence of the occupied dz2 and the empty pz orbitals perpendicular to the coordination plane means that higher coordination numbers can be achieved, with the cation acting as a Lewis base, a Lewis acid, or both (Aullón & Alvarez, 1996). In the title complex, the shortest distance between PdII centres and possible intramolecular sulfur donors are 4.5864 (10) Å and 4.3964 (9) Å for Pd1—S3 and Pd2—S4 respectively, and therefore does not constitute an interaction at either Pd site. The Pd1—Pd2 separation, however, is 3.3776 (3) Å, while the PdN2O2 plane-plane fold angle is 1.62 (7) °. A search for close (sum of the van der Waals radii, 3.26 Å, + 0.4 Å) Pd—Pd separations in the CSD v. 5.34 with Feb. 2013 update (Allen, 2002) yielded 1137 observations with an average value of 3.2 (3). Examination of the packed unit cell revealed a short intermolecular S—S contact between S5 and the inversion related S5iii (iii = 1 - x, 1 - y, 1 - z) measuring 3.663 (2) Å (Figure 3.)

Related literature top

For the synthesis of the ligand 5,8,11-trithia-2,14-diazapentadeca-1,14-diene-1,15-diyl)diphenolate, and the related complexes [2,2'-(5,8-dithia-2,11-diazododeca-1,11-diene-1,12-diyl)diphenolato]cobalt tetrafluoroborate and [2,2'-(5,8-dithia-2,11-diazododeca-1,11-diene-1,12-diyl)diphenolato]nickel acetate, see: Lucas et al. (2011a). For the preparation of the starting material, bis(acetonitrile)dichloropalladium(II), from which the title complex was synthesized, see: Mathews et al. (2003). For a copper complex containing the same ligand as the title complex, bis[µ2-2,2'-(5,8,11-trithia-2,14-diazapentadeca-1,14-diene-1,15-diyl)diphenolato]dicopper(II), see: Lucas et al. (2011b). Lucas et al. (2011b) also reports the related [2,2'-(5,8-dithia-2,11-diazadodeca-1,11-diene-1,12-diyl)diphenolato]copper(II). For Pd catalysts containing salicylaldimine (sal) ligands, see: Jin et al. (2010). For a discussion on the coordination capabilities of PdII, see: Aullón & Alvarez (1996). For a description of the Cambridge Crystallographic Database, see: Allen (2002).

Experimental top

All starting materials were obtained from the Aldrich Chemical Company and were used without further purification. Analyses were performed by Canadian Microanalytical Service Ltd.

Preparation of the complex, [2,2'-(5,8,11-Trithia-2,14-diazapentadeca-1,14-diene-1,15-diyl)diphenolato]palladium(II) acetonitrile monosolvate

Bis(acetonitrile)dichloropalladium(II) (0.259 g; 1.00 m mol) (Mathews et al., 2003) was dissolved in acetonitrile (50 ml) to give a yellow-orange solution. Likewise, 5,8,11-trithia-2,14-diazapentadeca-1,14-diene-1,15-diyl)diphenolate (0.449 g; 1.00 mmol) (Lucas et al. 2011a) was dissolved in acetonitrile (100 ml) to give a colourless solution. The solutions were mixed at room temperature, refluxed with stirring for 2 h, the volume reduced in a rotavap to ~75 ml and solvent then allowed to evaporate slowly at room temperature until orange crystals formed. These were removed by filtration at room temperature and dried in air to yield the product in 44% yield. Calc'd for C44H52N4O4Pd2S6.CH3CN: C 48.16; H 4.83; N 6.10; S 16.77. Found: C 48.08; H 4.72; N 6.49; S 16.25.

Refinement top

Hydrogen atoms were introduced into idealized positions and refined using the riding atom formalism (idealized Me refined as rotating group.) The applied constraints were: Cmethine—Hmethine = 0.98 Å, Cmethylene—Hmethylene = 0.97 Å, Cmethyl—Hmethyl = 0.96 Å; Uiso(Hmethine) = 1.2Ueq(Cmethine), Uiso(Hmethylene) = 1.2Ueq(Cmethylene), Uiso(Hmethyl) = 1.5Ueq(Cmethyl).

Part of the ligand chain in each complex was disordered with two orientiations. For S2—C12—C13—S3 and S2A—C12A—C13A—S3A (and the pertinent H-atoms) the occupancies were constrained to equal to 1, and the respective occupancies resulted in 0.450 (10) and 0.550 (10). For S5—C34—C35—S6 and S5A—C34A—C35A—S6A (and the pertinent H-atoms) the occupancies were also constrained to equal to 1, and the respective occupancies resulted in 0.789 (9) and 0.211 (9). Similarity restraints (the command SAME and SIMU from SHELXL-2013 by Sheldrick, 2008) were applied to {S2, C12, S2, C12A} {C13, S3, C13A, S3} {S5, C34, S6, C35} {S5, C34A, S6, C35A}. Distances were restrained (the command DFIX from SHELXL-2013 by Sheldrick, 2008) for S5—C34A and S2—C12.

Computing details top

Data collection: CrystalClear (Rigaku, 2005); cell refinement: CrystalClear (Rigaku, 2005); data reduction: CrystalClear (Rigaku, 2005); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL2013 (Sheldrick, 2008); molecular graphics: Mercury (Macrae et al., 2006) and ORTEP-3 for Windows (Farrugia, 2012); software used to prepare material for publication: OLEX2 (Dolomanov et al., 2009) and publCIF (Westrip, 2010).

Figures top
[Figure 1] Fig. 1. Asymmetric unit of the title compound, shown with 50% probability displacement ellipsoids. Labels for H-atoms, and C1, C6, C17, and C22 omitted for clarity.
[Figure 2] Fig. 2. Overlay of both Pd complexes present in the asymmetric unit. The molecule containing Pd1 is green, while the molecule containing Pd2 has the atom colouring scheme Pd = purple, S = yellow, O = red, N = blue, C = grey. H-atoms omitted from this analysis.
[Figure 3] Fig. 3. Packed unit cell for the title complex. H-atoms and minor disorder components omitted for clarity. Symmetry codes: (i) = 1 - x, -1/2 + y, 1/2 - z; (ii) = x, 1.5 - y, 1/2 + z; (iii) = 1 - x, 1 - y, 1 - z.
Bis{[2,2'-(5,8,11-trithia-2,14-diazapentadeca-1,14-diene-1,15-diyl)diphenolato]palladium(II)}{ acetonitrile hemisolvate top
Crystal data top
[Pd(C22H26N2O2S3)]2·0.5C2H3NF(000) = 2344
Mr = 1147.11Dx = 1.586 Mg m3
Monoclinic, P21/cMo Kα radiation, λ = 0.7107 Å
Hall symbol: -P 2ybcCell parameters from 22595 reflections
a = 14.7232 (5) Åθ = 1.4–30.7°
b = 16.2151 (5) ŵ = 1.06 mm1
c = 20.9433 (8) ÅT = 153 K
β = 106.087 (1)°Prism, yellow
V = 4804.2 (3) Å30.39 × 0.39 × 0.24 mm
Z = 4
Data collection top
Rigaku Saturn70
diffractometer
10948 independent reflections
Radiation source: Sealed Tube10673 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.025
Detector resolution: 28.5714 pixels mm-1θmax = 27.5°, θmin = 2.9°
ω scansh = 1919
Absorption correction: numerical
(ABSCOR; Higashi, 2000)
k = 2020
Tmin = 0.794, Tmax = 0.862l = 2727
53768 measured reflections
Refinement top
Refinement on F274 restraints
Least-squares matrix: fullHydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.041H-atom parameters constrained
wR(F2) = 0.104 w = 1/[σ2(Fo2) + (0.0515P)2 + 8.1878P]
where P = (Fo2 + 2Fc2)/3
S = 1.07(Δ/σ)max = 0.004
10948 reflectionsΔρmax = 1.16 e Å3
607 parametersΔρmin = 1.02 e Å3
Crystal data top
[Pd(C22H26N2O2S3)]2·0.5C2H3NV = 4804.2 (3) Å3
Mr = 1147.11Z = 4
Monoclinic, P21/cMo Kα radiation
a = 14.7232 (5) ŵ = 1.06 mm1
b = 16.2151 (5) ÅT = 153 K
c = 20.9433 (8) Å0.39 × 0.39 × 0.24 mm
β = 106.087 (1)°
Data collection top
Rigaku Saturn70
diffractometer
10948 independent reflections
Absorption correction: numerical
(ABSCOR; Higashi, 2000)
10673 reflections with I > 2σ(I)
Tmin = 0.794, Tmax = 0.862Rint = 0.025
53768 measured reflectionsθmax = 27.5°
Refinement top
R[F2 > 2σ(F2)] = 0.041H-atom parameters constrained
wR(F2) = 0.104Δρmax = 1.16 e Å3
S = 1.07Δρmin = 1.02 e Å3
10948 reflectionsAbsolute structure: ?
607 parametersAbsolute structure parameter: ?
74 restraintsRogers parameter: ?
Special details top

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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/UeqOcc. (<1)
Pd10.24528 (2)1.01728 (2)0.25397 (2)0.02431 (7)
Pd20.27766 (2)0.83920 (2)0.34103 (2)0.02261 (7)
S10.27034 (7)1.27406 (5)0.35638 (5)0.0436 (2)
S20.18287 (8)1.29247 (6)0.13677 (5)0.0542 (3)
C120.2051 (8)1.1866 (2)0.1194 (5)0.051 (3)0.450 (10)
H12A0.27391.17830.12680.061*0.450 (10)
H12B0.18391.14990.15020.061*0.450 (10)
C12A0.1402 (5)1.1877 (4)0.1129 (3)0.0362 (16)0.550 (10)
H12C0.13281.15750.15220.043*0.550 (10)
H12D0.07781.19000.07940.043*0.550 (10)
C130.1535 (7)1.1637 (5)0.0480 (5)0.050 (3)0.450 (10)
H13A0.17901.19760.01770.060*0.450 (10)
H13B0.08581.17770.03970.060*0.450 (10)
S30.16318 (7)1.05643 (6)0.02830 (5)0.0455 (2)
C13A0.2104 (4)1.1427 (4)0.0841 (3)0.0368 (17)0.550 (10)
H13C0.26231.12170.12140.044*0.550 (10)
H13D0.23831.18320.05950.044*0.550 (10)
S40.09765 (8)0.65616 (6)0.40186 (6)0.0517 (2)
S50.38682 (8)0.55470 (6)0.47534 (5)0.0515 (2)
C34A0.4263 (14)0.6403 (8)0.4351 (9)0.050 (5)0.211 (9)
H34A0.42440.62500.38900.060*0.211 (9)
H34B0.38350.68800.43320.060*0.211 (9)
S60.58158 (6)0.74205 (6)0.43321 (6)0.0513 (2)
C35A0.5288 (13)0.6647 (10)0.4741 (10)0.045 (5)0.211 (9)
H35A0.56890.61470.48110.054*0.211 (9)
H35B0.52830.68570.51840.054*0.211 (9)
C340.4646 (4)0.6428 (3)0.4825 (2)0.0435 (13)0.789 (9)
H34C0.43430.69140.49660.052*0.789 (9)
H34D0.52400.63150.51750.052*0.789 (9)
C350.4880 (4)0.6631 (3)0.4188 (2)0.0421 (13)0.789 (9)
H35C0.43070.68360.38570.051*0.789 (9)
H35D0.50950.61260.40070.051*0.789 (9)
O10.10969 (14)0.98736 (14)0.22468 (11)0.0348 (5)
O20.38175 (14)1.04476 (14)0.28401 (11)0.0336 (5)
O30.32370 (14)0.89742 (13)0.42772 (10)0.0294 (4)
O40.23161 (14)0.77858 (14)0.25591 (10)0.0322 (5)
N10.23177 (17)1.07243 (15)0.33818 (12)0.0262 (5)
N20.25695 (17)0.96422 (15)0.16926 (12)0.0274 (5)
N30.14478 (16)0.83256 (14)0.35040 (12)0.0249 (5)
N40.41045 (16)0.84643 (14)0.33121 (12)0.0256 (5)
N50.0113 (7)1.1934 (5)0.4860 (4)0.157 (3)
C10.04531 (19)1.00426 (18)0.25485 (15)0.0278 (6)
C20.0486 (2)0.97597 (19)0.22332 (18)0.0343 (7)
H20.06100.94700.18240.041*
C30.1207 (2)0.9903 (2)0.25155 (18)0.0383 (7)
H30.18250.97110.22990.046*
C40.1045 (2)1.0326 (2)0.31170 (18)0.0419 (8)
H40.15501.04230.33080.050*
C50.0150 (2)1.0602 (2)0.34308 (17)0.0378 (7)
H50.00421.08870.38410.045*
C60.0612 (2)1.04706 (18)0.31557 (14)0.0284 (6)
C70.1526 (2)1.07671 (18)0.35308 (14)0.0281 (6)
H70.15481.10280.39410.034*
C80.3150 (2)1.10684 (19)0.38663 (14)0.0303 (6)
H8A0.36671.06580.39510.036*
H8B0.29931.11630.42900.036*
C90.3503 (2)1.1876 (2)0.36453 (16)0.0333 (6)
H9A0.36331.17840.32120.040*
H9B0.41091.20240.39700.040*
C100.2018 (2)1.2663 (2)0.27020 (18)0.0410 (7)
H10A0.17701.20940.26160.049*
H10B0.14701.30400.26260.049*
C110.2570 (3)1.2868 (3)0.2211 (2)0.0520 (9)
H11A0.30611.24420.22380.062*
H11B0.28941.34040.23330.062*
C140.1084 (2)0.9958 (2)0.08026 (17)0.0395 (7)
H14A0.08781.03340.11080.047*
H14B0.05130.96870.05160.047*
C150.1726 (2)0.9301 (2)0.12107 (15)0.0318 (6)
H15A0.13610.89740.14530.038*
H15B0.19300.89240.09060.038*
C160.3354 (2)0.95802 (18)0.15369 (15)0.0291 (6)
H160.33190.93260.11220.035*
C170.4278 (2)0.98516 (18)0.19181 (15)0.0284 (6)
C180.5036 (2)0.9662 (2)0.16524 (16)0.0342 (6)
H180.49090.93840.12380.041*
C190.5947 (2)0.9869 (2)0.19757 (18)0.0388 (7)
H190.64490.97340.17910.047*
C200.6127 (2)1.0284 (2)0.25844 (18)0.0404 (7)
H200.67571.04360.28110.048*
C210.5405 (2)1.0475 (2)0.28593 (17)0.0354 (7)
H210.55461.07550.32730.042*
C220.4460 (2)1.02596 (18)0.25362 (15)0.0284 (6)
C230.27123 (19)0.93009 (17)0.46249 (13)0.0239 (5)
C240.3174 (2)0.97968 (18)0.51772 (14)0.0295 (6)
H240.38420.98480.52960.035*
C250.2674 (2)1.02042 (19)0.55435 (15)0.0341 (7)
H250.30011.05420.59050.041*
C260.1689 (2)1.0130 (2)0.53941 (15)0.0350 (7)
H260.13441.04280.56400.042*
C270.1235 (2)0.96191 (19)0.48844 (14)0.0296 (6)
H270.05720.95410.47960.035*
C280.17248 (19)0.92047 (17)0.44875 (13)0.0250 (5)
C290.11687 (19)0.86961 (17)0.39603 (14)0.0252 (5)
H290.05230.86250.39470.030*
C300.0742 (2)0.7805 (2)0.30476 (15)0.0323 (6)
H30A0.07370.79320.25840.039*
H30B0.01070.79330.30970.039*
C310.0947 (2)0.6890 (2)0.31811 (17)0.0384 (7)
H31A0.15650.67610.31030.046*
H31B0.04580.65670.28590.046*
C320.2233 (3)0.6526 (2)0.44326 (18)0.0482 (9)
H32A0.25250.70510.43530.058*
H32B0.23250.64730.49170.058*
C330.2735 (3)0.5813 (2)0.41969 (19)0.0489 (9)
H33A0.28240.59580.37590.059*
H33B0.23210.53200.41330.059*
C360.5182 (2)0.83366 (19)0.44539 (16)0.0331 (6)
H36A0.46290.81690.46050.040*
H36B0.56000.86730.48110.040*
C370.4843 (2)0.88662 (19)0.38354 (15)0.0293 (6)
H37A0.45950.93930.39570.035*
H37B0.53860.89960.36610.035*
C380.4345 (2)0.81974 (18)0.28014 (15)0.0294 (6)
H380.49870.82790.28100.035*
C390.3762 (2)0.77933 (18)0.22229 (15)0.0291 (6)
C400.4179 (2)0.76009 (19)0.17117 (16)0.0350 (7)
H400.48280.77260.17710.042*
C410.3672 (3)0.7238 (2)0.11291 (16)0.0395 (7)
H410.39640.71210.07870.047*
C420.2726 (3)0.7042 (2)0.10454 (16)0.0383 (7)
H420.23730.67870.06450.046*
C430.2293 (2)0.7215 (2)0.15391 (15)0.0341 (6)
H430.16500.70680.14770.041*
C440.2795 (2)0.76089 (17)0.21343 (14)0.0282 (6)
C450.0247 (5)1.2384 (5)0.4458 (3)0.098 (2)
C460.0420 (5)1.2925 (5)0.3953 (4)0.106 (2)
H46A0.00581.28270.35300.159*
H46B0.10501.28130.39010.159*
H46C0.03861.35000.40880.159*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Pd10.01968 (11)0.02473 (12)0.02705 (11)0.00004 (7)0.00403 (8)0.00088 (7)
Pd20.02143 (11)0.02333 (11)0.02199 (11)0.00194 (7)0.00422 (8)0.00289 (7)
S10.0497 (5)0.0313 (4)0.0478 (5)0.0008 (4)0.0101 (4)0.0047 (3)
S20.0727 (7)0.0348 (5)0.0494 (5)0.0012 (4)0.0076 (5)0.0115 (4)
C120.066 (7)0.040 (5)0.050 (5)0.004 (4)0.022 (4)0.006 (4)
C12A0.027 (3)0.040 (3)0.041 (3)0.005 (2)0.009 (2)0.008 (2)
C130.057 (6)0.043 (5)0.053 (5)0.005 (4)0.019 (5)0.011 (4)
S30.0485 (5)0.0461 (5)0.0387 (4)0.0025 (4)0.0067 (4)0.0033 (4)
C13A0.027 (3)0.038 (3)0.045 (4)0.005 (2)0.008 (3)0.008 (3)
S40.0623 (6)0.0443 (5)0.0603 (6)0.0112 (4)0.0365 (5)0.0002 (4)
S50.0603 (6)0.0481 (5)0.0456 (5)0.0120 (5)0.0138 (4)0.0002 (4)
C34A0.062 (12)0.039 (9)0.046 (11)0.004 (8)0.010 (9)0.001 (7)
S60.0334 (4)0.0425 (5)0.0810 (7)0.0107 (4)0.0208 (4)0.0133 (5)
C35A0.042 (9)0.027 (7)0.063 (12)0.004 (6)0.009 (8)0.018 (7)
C340.050 (3)0.044 (3)0.033 (3)0.001 (2)0.006 (2)0.0023 (18)
C350.056 (3)0.031 (2)0.042 (3)0.0071 (19)0.018 (2)0.0006 (17)
O10.0215 (10)0.0432 (13)0.0395 (12)0.0027 (9)0.0084 (9)0.0106 (9)
O20.0223 (9)0.0429 (12)0.0342 (11)0.0008 (9)0.0054 (8)0.0087 (9)
O30.0228 (9)0.0359 (11)0.0279 (10)0.0019 (8)0.0046 (8)0.0115 (8)
O40.0287 (10)0.0407 (12)0.0274 (10)0.0074 (9)0.0082 (8)0.0132 (9)
N10.0259 (11)0.0241 (11)0.0274 (11)0.0022 (9)0.0055 (9)0.0017 (9)
N20.0255 (11)0.0265 (12)0.0286 (12)0.0005 (9)0.0047 (9)0.0040 (9)
N30.0204 (10)0.0265 (12)0.0256 (11)0.0009 (9)0.0027 (9)0.0039 (9)
N40.0218 (11)0.0255 (12)0.0284 (12)0.0027 (9)0.0054 (9)0.0016 (9)
N50.255 (10)0.130 (6)0.092 (5)0.069 (6)0.059 (6)0.005 (4)
C10.0215 (13)0.0242 (13)0.0379 (15)0.0013 (10)0.0088 (11)0.0054 (11)
C20.0245 (14)0.0280 (15)0.0487 (18)0.0015 (11)0.0070 (13)0.0018 (13)
C30.0227 (14)0.0371 (17)0.054 (2)0.0008 (12)0.0092 (13)0.0097 (14)
C40.0293 (15)0.054 (2)0.0468 (19)0.0048 (14)0.0175 (14)0.0135 (16)
C50.0361 (16)0.0458 (19)0.0342 (16)0.0047 (14)0.0142 (13)0.0072 (13)
C60.0267 (13)0.0269 (14)0.0314 (14)0.0029 (11)0.0077 (11)0.0091 (11)
C70.0316 (14)0.0274 (14)0.0253 (13)0.0039 (11)0.0080 (11)0.0038 (10)
C80.0296 (14)0.0325 (15)0.0251 (13)0.0023 (12)0.0015 (11)0.0001 (11)
C90.0247 (13)0.0341 (16)0.0389 (16)0.0034 (12)0.0052 (12)0.0020 (12)
C100.0365 (17)0.0332 (16)0.0494 (19)0.0033 (13)0.0055 (14)0.0065 (14)
C110.047 (2)0.051 (2)0.054 (2)0.0018 (17)0.0072 (17)0.0011 (18)
C140.0289 (15)0.0462 (19)0.0375 (17)0.0015 (14)0.0009 (13)0.0011 (14)
C150.0260 (13)0.0352 (16)0.0309 (14)0.0028 (12)0.0026 (11)0.0091 (12)
C160.0263 (13)0.0304 (14)0.0291 (14)0.0042 (11)0.0051 (11)0.0005 (11)
C170.0267 (14)0.0263 (14)0.0315 (14)0.0026 (11)0.0071 (11)0.0045 (11)
C180.0307 (15)0.0395 (17)0.0335 (15)0.0036 (13)0.0104 (12)0.0038 (13)
C190.0258 (14)0.049 (2)0.0436 (18)0.0034 (13)0.0133 (13)0.0081 (14)
C200.0240 (14)0.0446 (19)0.050 (2)0.0030 (13)0.0056 (13)0.0049 (15)
C210.0266 (14)0.0373 (17)0.0386 (16)0.0022 (12)0.0032 (12)0.0024 (13)
C220.0238 (13)0.0266 (14)0.0348 (15)0.0009 (11)0.0079 (11)0.0020 (11)
C230.0281 (13)0.0231 (12)0.0204 (12)0.0037 (10)0.0066 (10)0.0006 (9)
C240.0323 (14)0.0304 (15)0.0243 (13)0.0058 (12)0.0055 (11)0.0019 (11)
C250.0423 (17)0.0348 (16)0.0233 (13)0.0067 (13)0.0062 (12)0.0084 (11)
C260.0399 (17)0.0380 (17)0.0288 (15)0.0011 (13)0.0124 (13)0.0048 (12)
C270.0287 (14)0.0326 (15)0.0279 (14)0.0005 (12)0.0086 (11)0.0012 (11)
C280.0272 (13)0.0248 (13)0.0220 (12)0.0016 (11)0.0051 (10)0.0016 (10)
C290.0233 (12)0.0249 (13)0.0271 (13)0.0000 (10)0.0064 (10)0.0007 (10)
C300.0217 (13)0.0388 (16)0.0336 (15)0.0039 (12)0.0033 (11)0.0122 (12)
C310.0378 (16)0.0346 (16)0.0431 (18)0.0115 (14)0.0116 (14)0.0127 (13)
C320.073 (3)0.0411 (19)0.0332 (17)0.0045 (18)0.0187 (17)0.0019 (14)
C330.067 (2)0.0416 (19)0.0387 (18)0.0001 (18)0.0150 (17)0.0001 (15)
C360.0272 (14)0.0305 (15)0.0367 (16)0.0024 (12)0.0006 (12)0.0006 (12)
C370.0228 (13)0.0300 (14)0.0336 (15)0.0059 (11)0.0055 (11)0.0010 (11)
C380.0257 (13)0.0297 (14)0.0341 (15)0.0002 (11)0.0107 (11)0.0007 (11)
C390.0323 (14)0.0251 (13)0.0311 (14)0.0018 (11)0.0106 (11)0.0008 (11)
C400.0409 (17)0.0301 (15)0.0384 (16)0.0037 (13)0.0184 (14)0.0006 (12)
C410.054 (2)0.0360 (17)0.0338 (16)0.0035 (15)0.0206 (15)0.0030 (13)
C420.0536 (19)0.0321 (16)0.0283 (15)0.0028 (14)0.0097 (14)0.0062 (12)
C430.0391 (16)0.0304 (15)0.0315 (15)0.0026 (13)0.0074 (13)0.0073 (12)
C440.0357 (15)0.0253 (13)0.0236 (13)0.0021 (11)0.0083 (11)0.0015 (10)
C450.117 (5)0.095 (5)0.080 (4)0.011 (4)0.024 (4)0.008 (4)
C460.105 (5)0.109 (5)0.110 (5)0.001 (4)0.038 (4)0.012 (4)
Geometric parameters (Å, º) top
Pd1—O11.980 (2)C8—H8B0.9900
Pd1—O21.983 (2)C8—C91.528 (4)
Pd1—N12.036 (2)C9—H9A0.9900
Pd1—N22.021 (2)C9—H9B0.9900
Pd2—O31.9913 (19)C10—H10A0.9900
Pd2—O41.9836 (19)C10—H10B0.9900
Pd2—N32.022 (2)C10—C111.515 (5)
Pd2—N42.025 (2)C11—H11A0.9900
S1—C91.808 (3)C11—H11B0.9900
S1—C101.812 (4)C14—H14A0.9900
S2—C121.804 (2)C14—H14B0.9900
S2—C12A1.833 (6)C14—C151.519 (4)
S2—C111.802 (4)C15—H15A0.9900
C12—H12A0.9900C15—H15B0.9900
C12—H12B0.9900C16—H160.9500
C12—C131.522 (14)C16—C171.443 (4)
C12A—H12C0.9900C17—C181.411 (4)
C12A—H12D0.9900C17—C221.412 (4)
C12A—C13A1.519 (9)C18—H180.9500
C13—H13A0.9900C18—C191.367 (4)
C13—H13B0.9900C19—H190.9500
C13—S31.803 (9)C19—C201.400 (5)
S3—C13A1.832 (7)C20—H200.9500
S3—C141.813 (4)C20—C211.377 (5)
C13A—H13C0.9900C21—H210.9500
C13A—H13D0.9900C21—C221.413 (4)
S4—C311.822 (4)C23—C241.418 (4)
S4—C321.813 (5)C23—C281.410 (4)
S5—C34A1.802 (2)C24—H240.9500
S5—C341.811 (5)C24—C251.371 (4)
S5—C331.803 (4)C25—H250.9500
C34A—H34A0.9900C25—C261.401 (5)
C34A—H34B0.9900C26—H260.9500
C34A—C35A1.55 (3)C26—C271.371 (4)
S6—C35A1.810 (17)C27—H270.9500
S6—C351.843 (5)C27—C281.413 (4)
S6—C361.809 (3)C28—C291.438 (4)
C35A—H35A0.9900C29—H290.9500
C35A—H35B0.9900C30—H30A0.9900
C34—H34C0.9900C30—H30B0.9900
C34—H34D0.9900C30—C311.524 (5)
C34—C351.504 (7)C31—H31A0.9900
C35—H35C0.9900C31—H31B0.9900
C35—H35D0.9900C32—H32A0.9900
O1—C11.306 (4)C32—H32B0.9900
O2—C221.313 (4)C32—C331.526 (5)
O3—C231.311 (3)C33—H33A0.9900
O4—C441.311 (3)C33—H33B0.9900
N1—C71.290 (4)C36—H36A0.9900
N1—C81.468 (4)C36—H36B0.9900
N2—C151.474 (4)C36—C371.519 (4)
N2—C161.288 (4)C37—H37A0.9900
N3—C291.289 (4)C37—H37B0.9900
N3—C301.468 (3)C38—H380.9500
N4—C371.465 (3)C38—C391.435 (4)
N4—C381.291 (4)C39—C401.409 (4)
N5—C451.170 (9)C39—C441.415 (4)
C1—C21.432 (4)C40—H400.9500
C1—C61.410 (4)C40—C411.374 (5)
C2—H20.9500C41—H410.9500
C2—C31.370 (5)C41—C421.391 (5)
C3—H30.9500C42—H420.9500
C3—C41.396 (5)C42—C431.385 (4)
C4—H40.9500C43—H430.9500
C4—C51.374 (5)C43—C441.413 (4)
C5—H50.9500C45—C461.450 (9)
C5—C61.413 (4)C46—H46A0.9800
C6—C71.439 (4)C46—H46B0.9800
C7—H70.9500C46—H46C0.9800
C8—H8A0.9900
O1—Pd1—O2178.75 (10)S2—C11—H11A109.1
O1—Pd1—N192.51 (9)S2—C11—H11B109.1
O1—Pd1—N286.99 (9)C10—C11—S2112.5 (3)
O2—Pd1—N187.71 (9)C10—C11—H11A109.1
O2—Pd1—N292.81 (9)C10—C11—H11B109.1
N2—Pd1—N1178.86 (10)H11A—C11—H11B107.8
O3—Pd2—N391.77 (9)S3—C14—H14A108.7
O3—Pd2—N488.33 (9)S3—C14—H14B108.7
O4—Pd2—O3178.54 (9)H14A—C14—H14B107.6
O4—Pd2—N387.81 (9)C15—C14—S3114.1 (2)
O4—Pd2—N492.10 (9)C15—C14—H14A108.7
N3—Pd2—N4179.63 (10)C15—C14—H14B108.7
C9—S1—C10102.04 (16)N2—C15—C14113.4 (3)
C11—S2—C1293.2 (4)N2—C15—H15A108.9
C11—S2—C12A106.8 (2)N2—C15—H15B108.9
S2—C12—H12A109.4C14—C15—H15A108.9
S2—C12—H12B109.4C14—C15—H15B108.9
H12A—C12—H12B108.0H15A—C15—H15B107.7
C13—C12—S2111.2 (6)N2—C16—H16116.2
C13—C12—H12A109.4N2—C16—C17127.6 (3)
C13—C12—H12B109.4C17—C16—H16116.2
S2—C12A—H12C109.8C18—C17—C16116.3 (3)
S2—C12A—H12D109.8C18—C17—C22119.6 (3)
H12C—C12A—H12D108.2C22—C17—C16124.1 (3)
C13A—C12A—S2109.5 (4)C17—C18—H18119.1
C13A—C12A—H12C109.8C19—C18—C17121.7 (3)
C13A—C12A—H12D109.8C19—C18—H18119.1
C12—C13—H13A108.7C18—C19—H19120.6
C12—C13—H13B108.7C18—C19—C20118.8 (3)
C12—C13—S3114.2 (6)C20—C19—H19120.6
H13A—C13—H13B107.6C19—C20—H20119.5
S3—C13—H13A108.7C21—C20—C19121.0 (3)
S3—C13—H13B108.7C21—C20—H20119.5
C13—S3—C14108.0 (3)C20—C21—H21119.4
C14—S3—C13A100.6 (2)C20—C21—C22121.1 (3)
C12A—C13A—S3116.1 (4)C22—C21—H21119.4
C12A—C13A—H13C108.3O2—C22—C17125.1 (3)
C12A—C13A—H13D108.3O2—C22—C21117.2 (3)
S3—C13A—H13C108.3C17—C22—C21117.7 (3)
S3—C13A—H13D108.3O3—C23—C24117.3 (2)
H13C—C13A—H13D107.4O3—C23—C28125.1 (2)
C32—S4—C31102.62 (16)C28—C23—C24117.6 (3)
C34A—S5—C3382.8 (7)C23—C24—H24119.3
C33—S5—C34108.4 (2)C25—C24—C23121.3 (3)
S5—C34A—H34A109.7C25—C24—H24119.3
S5—C34A—H34B109.7C24—C25—H25119.4
H34A—C34A—H34B108.2C24—C25—C26121.1 (3)
C35A—C34A—S5110.0 (11)C26—C25—H25119.4
C35A—C34A—H34A109.7C25—C26—H26120.8
C35A—C34A—H34B109.7C27—C26—C25118.5 (3)
C36—S6—C35A101.3 (6)C27—C26—H26120.8
C36—S6—C35101.68 (18)C26—C27—H27119.1
C34A—C35A—S6114.2 (11)C26—C27—C28121.8 (3)
C34A—C35A—H35A108.7C28—C27—H27119.1
C34A—C35A—H35B108.7C23—C28—C27119.5 (3)
S6—C35A—H35A108.7C23—C28—C29123.8 (3)
S6—C35A—H35B108.7C27—C28—C29116.7 (3)
H35A—C35A—H35B107.6N3—C29—C28127.3 (3)
S5—C34—H34C108.9N3—C29—H29116.4
S5—C34—H34D108.9C28—C29—H29116.4
H34C—C34—H34D107.7N3—C30—H30A109.3
C35—C34—S5113.2 (3)N3—C30—H30B109.3
C35—C34—H34C108.9N3—C30—C31111.8 (2)
C35—C34—H34D108.9H30A—C30—H30B107.9
S6—C35—H35C109.5C31—C30—H30A109.3
S6—C35—H35D109.5C31—C30—H30B109.3
C34—C35—S6110.6 (3)S4—C31—H31A108.7
C34—C35—H35C109.5S4—C31—H31B108.7
C34—C35—H35D109.5C30—C31—S4114.3 (2)
H35C—C35—H35D108.1C30—C31—H31A108.7
C1—O1—Pd1127.13 (19)C30—C31—H31B108.7
C22—O2—Pd1126.60 (19)H31A—C31—H31B107.6
C23—O3—Pd2126.43 (17)S4—C32—H32A109.0
C44—O4—Pd2127.16 (19)S4—C32—H32B109.0
C7—N1—Pd1123.0 (2)H32A—C32—H32B107.8
C7—N1—C8116.7 (2)C33—C32—S4113.0 (3)
C8—N1—Pd1120.18 (19)C33—C32—H32A109.0
C15—N2—Pd1120.00 (19)C33—C32—H32B109.0
C16—N2—Pd1123.8 (2)S5—C33—H33A108.6
C16—N2—C15116.2 (2)S5—C33—H33B108.6
C29—N3—Pd2124.26 (19)C32—C33—S5114.6 (3)
C29—N3—C30115.9 (2)C32—C33—H33A108.6
C30—N3—Pd2119.78 (18)C32—C33—H33B108.6
C37—N4—Pd2119.14 (18)H33A—C33—H33B107.6
C38—N4—Pd2124.0 (2)S6—C36—H36A108.8
C38—N4—C37116.8 (2)S6—C36—H36B108.8
O1—C1—C2116.5 (3)H36A—C36—H36B107.7
O1—C1—C6125.3 (3)C37—C36—S6113.9 (2)
C6—C1—C2118.1 (3)C37—C36—H36A108.8
C1—C2—H2119.6C37—C36—H36B108.8
C3—C2—C1120.7 (3)N4—C37—C36112.8 (2)
C3—C2—H2119.6N4—C37—H37A109.0
C2—C3—H3119.5N4—C37—H37B109.0
C2—C3—C4120.9 (3)C36—C37—H37A109.0
C4—C3—H3119.5C36—C37—H37B109.0
C3—C4—H4120.2H37A—C37—H37B107.8
C5—C4—C3119.5 (3)N4—C38—H38116.0
C5—C4—H4120.2N4—C38—C39128.0 (3)
C4—C5—H5119.3C39—C38—H38116.0
C4—C5—C6121.4 (3)C40—C39—C38117.2 (3)
C6—C5—H5119.3C40—C39—C44119.2 (3)
C1—C6—C5119.3 (3)C44—C39—C38123.5 (3)
C1—C6—C7123.6 (3)C39—C40—H40119.2
C5—C6—C7117.1 (3)C41—C40—C39121.7 (3)
N1—C7—C6128.4 (3)C41—C40—H40119.2
N1—C7—H7115.8C40—C41—H41120.4
C6—C7—H7115.8C40—C41—C42119.2 (3)
N1—C8—H8A108.8C42—C41—H41120.4
N1—C8—H8B108.8C41—C42—H42119.6
N1—C8—C9113.9 (2)C43—C42—C41120.7 (3)
H8A—C8—H8B107.7C43—C42—H42119.6
C9—C8—H8A108.8C42—C43—H43119.5
C9—C8—H8B108.8C42—C43—C44120.9 (3)
S1—C9—H9A108.5C44—C43—H43119.5
S1—C9—H9B108.5O4—C44—C39125.1 (3)
C8—C9—S1115.2 (2)O4—C44—C43116.7 (3)
C8—C9—H9A108.5C43—C44—C39118.2 (3)
C8—C9—H9B108.5N5—C45—C46178.7 (9)
H9A—C9—H9B107.5C45—C46—H46A109.5
S1—C10—H10A108.8C45—C46—H46B109.5
S1—C10—H10B108.8C45—C46—H46C109.5
H10A—C10—H10B107.7H46A—C46—H46B109.5
C11—C10—S1114.0 (3)H46A—C46—H46C109.5
C11—C10—H10A108.8H46B—C46—H46C109.5
C11—C10—H10B108.8
Pd1—O1—C1—C2179.8 (2)C2—C3—C4—C50.1 (5)
Pd1—O1—C1—C60.8 (4)C3—C4—C5—C60.4 (5)
Pd1—O2—C22—C172.8 (4)C4—C5—C6—C10.4 (5)
Pd1—O2—C22—C21176.3 (2)C4—C5—C6—C7178.6 (3)
Pd1—N1—C7—C61.3 (4)C5—C6—C7—N1179.6 (3)
Pd1—N1—C8—C974.4 (3)C6—C1—C2—C30.0 (4)
Pd1—N2—C15—C1475.9 (3)C7—N1—C8—C9107.9 (3)
Pd1—N2—C16—C170.9 (4)C8—N1—C7—C6179.0 (3)
Pd2—O3—C23—C24170.55 (19)C9—S1—C10—C1169.8 (3)
Pd2—O3—C23—C288.7 (4)C10—S1—C9—C890.7 (3)
Pd2—O4—C44—C392.9 (4)C11—S2—C12—C13179.2 (7)
Pd2—O4—C44—C43176.0 (2)C11—S2—C12A—C13A88.3 (4)
Pd2—N3—C29—C281.2 (4)C14—S3—C13A—C12A53.6 (5)
Pd2—N3—C30—C3170.9 (3)C15—N2—C16—C17179.3 (3)
Pd2—N4—C37—C3675.0 (3)C16—N2—C15—C14103.9 (3)
Pd2—N4—C38—C391.4 (4)C16—C17—C18—C19178.4 (3)
S1—C10—C11—S2171.9 (2)C16—C17—C22—O20.4 (5)
S2—C12—C13—S3174.8 (5)C16—C17—C22—C21178.7 (3)
S2—C12A—C13A—S3156.5 (3)C17—C18—C19—C200.4 (5)
C12—S2—C12A—C13A22.9 (7)C18—C17—C22—O2178.1 (3)
C12—S2—C11—C1094.3 (4)C18—C17—C22—C211.0 (4)
C12—C13—S3—C13A18.9 (6)C18—C19—C20—C210.7 (5)
C12—C13—S3—C1462.5 (8)C19—C20—C21—C220.1 (5)
C12A—S2—C12—C1361.4 (9)C20—C21—C22—O2178.5 (3)
C12A—S2—C11—C1067.6 (4)C20—C21—C22—C170.8 (5)
C13—S3—C13A—C12A53.3 (7)C22—C17—C18—C190.5 (5)
C13—S3—C14—C15124.9 (4)C23—C24—C25—C261.4 (5)
S3—C14—C15—N262.7 (3)C23—C28—C29—N37.3 (5)
C13A—S3—C14—C1592.2 (3)C24—C23—C28—C272.0 (4)
S4—C32—C33—S5161.3 (2)C24—C23—C28—C29177.6 (3)
S5—C34A—C35A—S6173.0 (9)C24—C25—C26—C272.0 (5)
S5—C34—C35—S6171.0 (2)C25—C26—C27—C283.5 (5)
C34A—S5—C34—C3527.6 (12)C26—C27—C28—C231.5 (4)
C34A—S5—C33—C3281.6 (7)C26—C27—C28—C29179.0 (3)
S6—C36—C37—N467.5 (3)C27—C28—C29—N3173.2 (3)
C35A—S6—C35—C3420.5 (10)C28—C23—C24—C253.4 (4)
C35A—S6—C36—C37134.9 (7)C29—N3—C30—C31106.9 (3)
C34—S5—C34A—C35A24.5 (10)C30—N3—C29—C28176.6 (3)
C34—S5—C33—C3262.1 (3)C31—S4—C32—C3371.1 (3)
C35—S6—C35A—C34A21.3 (9)C32—S4—C31—C3099.9 (3)
C35—S6—C36—C3797.5 (3)C33—S5—C34A—C35A167.9 (14)
O1—C1—C2—C3179.5 (3)C33—S5—C34—C3566.2 (4)
O1—C1—C6—C5179.2 (3)C36—S6—C35A—C34A73.1 (14)
O1—C1—C6—C71.1 (5)C36—S6—C35—C3472.8 (3)
O3—C23—C24—C25175.9 (3)C37—N4—C38—C39179.3 (3)
O3—C23—C28—C27177.3 (3)C38—N4—C37—C36107.1 (3)
O3—C23—C28—C293.2 (4)C38—C39—C40—C41177.9 (3)
N1—C8—C9—S165.7 (3)C38—C39—C44—O40.5 (5)
N2—C16—C17—C18176.1 (3)C38—C39—C44—C43179.4 (3)
N2—C16—C17—C221.7 (5)C39—C40—C41—C421.1 (5)
N3—C30—C31—S459.1 (3)C40—C39—C44—O4177.2 (3)
N4—C38—C39—C40176.5 (3)C40—C39—C44—C431.7 (4)
N4—C38—C39—C441.3 (5)C40—C41—C42—C430.5 (5)
C1—C2—C3—C40.1 (5)C41—C42—C43—C441.2 (5)
C1—C6—C7—N12.4 (5)C42—C43—C44—O4176.7 (3)
C2—C1—C6—C50.2 (4)C42—C43—C44—C392.3 (5)
C2—C1—C6—C7178.3 (3)C44—C39—C40—C410.1 (5)

Experimental details

Crystal data
Chemical formula[Pd(C22H26N2O2S3)]2·0.5C2H3N
Mr1147.11
Crystal system, space groupMonoclinic, P21/c
Temperature (K)153
a, b, c (Å)14.7232 (5), 16.2151 (5), 20.9433 (8)
β (°) 106.087 (1)
V3)4804.2 (3)
Z4
Radiation typeMo Kα
µ (mm1)1.06
Crystal size (mm)0.39 × 0.39 × 0.24
Data collection
DiffractometerRigaku Saturn70
diffractometer
Absorption correctionNumerical
(ABSCOR; Higashi, 2000)
Tmin, Tmax0.794, 0.862
No. of measured, independent and
observed [I > 2σ(I)] reflections
53768, 10948, 10673
Rint0.025
(sin θ/λ)max1)0.650
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.041, 0.104, 1.07
No. of reflections10948
No. of parameters607
No. of restraints74
H-atom treatmentH-atom parameters constrained
Δρmax, Δρmin (e Å3)1.16, 1.02

Computer programs: CrystalClear (Rigaku, 2005), SHELXS97 (Sheldrick, 2008), SHELXL2013 (Sheldrick, 2008), Mercury (Macrae et al., 2006) and ORTEP-3 for Windows (Farrugia, 2012), OLEX2 (Dolomanov et al., 2009) and publCIF (Westrip, 2010).

Acknowledgements top

Financial assistance from the Memorial University of Newfoundland is acknowledged.

references
References top

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