metal-organic compounds
κ2S,S)[2-(pyridin-2-yl)phenyl-κ2C1,N]palladium(II)
of (piperidine-1-carbodithioato-aCentre for Analysis and Synthesis, Department of Chemistry, Lund University, PO Box 124, S-221 00 Lund, Sweden
*Correspondence e-mail: ola.wendt@chem.lu.se
The title compound, [Pd(C11H8N)(C6H10NS2)], crystallizes with three similar and discrete molecules in the The CNS2 donor set defines a distorted square-planar geometry around the PdII atom, with very small deviations from planarity. The bidentate nature of the ligands gives fairly large deviations from the ideal 90° angles; the C—Pd—N angles are all around 81° and the S—Pd—S angles are around 75°. Molecules pack via dispersion interactions.
Keywords: crystal structure; palladium; phenylpyridine; dithiocarbamate.
CCDC reference: 1418104
1. Related literature
For structures of phenylpyridine with palladium, see: Nasielski et al. (2010). For a hexathiaadamantane structure with an S—Pd—S moiety, see: Pickardt & Rautenberg (1986). For examples of dinuclear palladium(II) complexes relevant to possible C—H activation, see: Powers et al. (2009, 2010). For the preparation of the dithiocarbamic acid, see: Kiss (2007).
2. Experimental
2.1. Crystal data
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2.3. Refinement
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Data collection: CrysAlis PRO (Agilent, 2011); cell CrysAlis PRO; data reduction: CrysAlis PRO; program(s) used to solve structure: SIR92 (Altomare et al., 1994); program(s) used to refine structure: SHELXL2014 (Sheldrick, 2008); molecular graphics: CrystalMaker (CrystalMaker, 2011); software used to prepare material for publication: SHELXL2014 (Sheldrick, 2008).
Supporting information
CCDC reference: 1418104
https://doi.org/10.1107/S2056989015015005/tk5379sup1.cif
contains datablock I. DOI:Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S2056989015015005/tk5379Isup2.hkl
We were interested in synthesizing dinuclear PdII complexes because of their possible involvement in C—H activation (Powers et al., 2009; Powers et al., 2010). The title compound was synthesized by a ligand exchange from a corresponding acetate-bridged dimer (Powers et al. (2009) and N-piperidinedithiocarbamic acid (Kiss, 2007). However, despite the isoelectronic structure and similar geometry of acetate and dithiocarbamate, the product formed was found to have a monomeric structure. The likely explanation for this difference is that the larger atomic radius and longer bonds of sulfur decrease the strain in the four-membered ring that is formed in a monomeric structure. The σ-C compared to the nitrogen is clearly seen in the Pd–S bond which is approximately 0.1 Å longer trans to carbon.
contains three discrete molecules and there is no indication of any strong intermolecular forces; packing is by dispersion.The natural bite angle of the ligands make the angles smaller than 90° and there is good agreement with other phenylpyridine palladium(II) complexes (Nasielski et al. 2010), and also with an example of a hexathiaadamantane structure displaying the same S–Pd–S moiety as seen here (Pickardt and Rautenberg, 1986). Bond distances are unremarkable and the higher trans influence of theIn air, [(phpy)PdOAc]2 (20 mg, 0.034 mmol, 1 equiv) was added to a solution of N-piperidinedithiocarbamic acid (11 mg, 0.068 mmol, 2 equiv) in MeCN (10 mL). The resulting solution was stirred overnight at 40°C, and then it was cooled to RT. The reaction mixture was concentrated to ~1mL and a mixture of Et2O/pentane (3:1, 5 mL) was added. The bright-yellow precipitate formed was filtered off and washed with mixture of Et2O/pentane (3:1, 3x2 mL) and dried. 23 mg (80%) of the title compound was obtained. X-ray quality crystals were obtained by recrystallization from a CH2Cl2/MeCN solution.
1H NMR (500 MHz, CD2Cl2): d 8.38 (d, J = 5 Hz, 1H, H1), 7.86 (m, 1H, H3), 7.80 (d, J = 8 Hz, 1H, H4), 7.59 (dd, J = 7, 1 Hz, 1H, H7), 7.20 – 7.00 (m, 4H, H2,8-10), 4.01 (dd, J = 11, 5 Hz, 4H, H13+17), 1.80 – 1.64 (m, 6H, H14-16)
We were interested in synthesizing dinuclear PdII complexes because of their possible involvement in C—H activation (Powers et al., 2009; Powers et al., 2010). The title compound was synthesized by a ligand exchange from a corresponding acetate-bridged dimer (Powers et al. (2009) and N-piperidinedithiocarbamic acid (Kiss, 2007). However, despite the isoelectronic structure and similar geometry of acetate and dithiocarbamate, the product formed was found to have a monomeric structure. The likely explanation for this difference is that the larger atomic radius and longer bonds of sulfur decrease the strain in the four-membered ring that is formed in a monomeric structure. The σ-C compared to the nitrogen is clearly seen in the Pd–S bond which is approximately 0.1 Å longer trans to carbon.
contains three discrete molecules and there is no indication of any strong intermolecular forces; packing is by dispersion.The natural bite angle of the ligands make the angles smaller than 90° and there is good agreement with other phenylpyridine palladium(II) complexes (Nasielski et al. 2010), and also with an example of a hexathiaadamantane structure displaying the same S–Pd–S moiety as seen here (Pickardt and Rautenberg, 1986). Bond distances are unremarkable and the higher trans influence of theFor structures of phenylpyridine with palladium, see: Nasielski et al. (2010). For a hexathioadamantane structure with an S—Pd—S moiety, see: Pickardt & Rautenberg (1986). For examples of dinuclear palladium(II) complexes relevant to possible C—H activation, see: Powers et al. (2009, 2010). For the preparation of the dithiocarbamic acid, see: Kiss (2007).
In air, [(phpy)PdOAc]2 (20 mg, 0.034 mmol, 1 equiv) was added to a solution of N-piperidinedithiocarbamic acid (11 mg, 0.068 mmol, 2 equiv) in MeCN (10 mL). The resulting solution was stirred overnight at 40°C, and then it was cooled to RT. The reaction mixture was concentrated to ~1mL and a mixture of Et2O/pentane (3:1, 5 mL) was added. The bright-yellow precipitate formed was filtered off and washed with mixture of Et2O/pentane (3:1, 3x2 mL) and dried. 23 mg (80%) of the title compound was obtained. X-ray quality crystals were obtained by recrystallization from a CH2Cl2/MeCN solution.
1H NMR (500 MHz, CD2Cl2): d 8.38 (d, J = 5 Hz, 1H, H1), 7.86 (m, 1H, H3), 7.80 (d, J = 8 Hz, 1H, H4), 7.59 (dd, J = 7, 1 Hz, 1H, H7), 7.20 – 7.00 (m, 4H, H2,8-10), 4.01 (dd, J = 11, 5 Hz, 4H, H13+17), 1.80 – 1.64 (m, 6H, H14-16)
detailsThe H atoms were positioned geometrically and treated as riding on their parent atoms with C–H distances of 0.93–0.97 Å, and with Uiso(H) = 1.2 Ueq.
Data collection: CrysAlis PRO (Agilent, 2011); cell
CrysAlis PRO (Agilent, 2011); data reduction: CrysAlis PRO (Agilent, 2011); program(s) used to solve structure: SIR92 (Altomare et al., 1994); program(s) used to refine structure: SHELXL2014 (Sheldrick, 2008); molecular graphics: CrystalMaker (CrystalMaker, 2011); software used to prepare material for publication: SHELXL2014 (Sheldrick, 2008).Fig. 1. The molecular structure of one of the molecules in the asymmetric unit with atom labels and 50% probability displacement ellipsoids. H-atoms are omitted for clarity. |
[Pd(C11H8N)(C6H10NS2)] | F(000) = 2544 |
Mr = 420.85 | Dx = 1.663 Mg m−3 |
Monoclinic, P21/c | Mo Kα radiation, λ = 0.71073 Å |
a = 24.0780 (9) Å | Cell parameters from 8955 reflections |
b = 8.5585 (2) Å | θ = 2.5–29.0° |
c = 26.6841 (10) Å | µ = 1.35 mm−1 |
β = 113.514 (4)° | T = 293 K |
V = 5042.2 (3) Å3 | Plate, yellow |
Z = 12 | 0.25 × 0.15 × 0.03 mm |
Agilent Xcalibur Sapphire3 diffractometer | 12332 independent reflections |
Radiation source: Enhance (Mo) X-ray Source | 8246 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.057 |
Detector resolution: 16.1829 pixels mm-1 | θmax = 29.1°, θmin = 2.5° |
ω scans | h = −32→31 |
Absorption correction: multi-scan (CrysAlis PRO; Agilent, 2011) | k = −11→11 |
Tmin = 0.604, Tmax = 1.000 | l = −34→35 |
58403 measured reflections |
Refinement on F2 | 0 restraints |
Least-squares matrix: full | Hydrogen site location: inferred from neighbouring sites |
R[F2 > 2σ(F2)] = 0.052 | H-atom parameters constrained |
wR(F2) = 0.096 | w = 1/[σ2(Fo2) + (0.0258P)2 + 4.0221P] where P = (Fo2 + 2Fc2)/3 |
S = 1.08 | (Δ/σ)max = 0.001 |
12332 reflections | Δρmax = 0.78 e Å−3 |
595 parameters | Δρmin = −0.69 e Å−3 |
[Pd(C11H8N)(C6H10NS2)] | V = 5042.2 (3) Å3 |
Mr = 420.85 | Z = 12 |
Monoclinic, P21/c | Mo Kα radiation |
a = 24.0780 (9) Å | µ = 1.35 mm−1 |
b = 8.5585 (2) Å | T = 293 K |
c = 26.6841 (10) Å | 0.25 × 0.15 × 0.03 mm |
β = 113.514 (4)° |
Agilent Xcalibur Sapphire3 diffractometer | 12332 independent reflections |
Absorption correction: multi-scan (CrysAlis PRO; Agilent, 2011) | 8246 reflections with I > 2σ(I) |
Tmin = 0.604, Tmax = 1.000 | Rint = 0.057 |
58403 measured reflections |
R[F2 > 2σ(F2)] = 0.052 | 0 restraints |
wR(F2) = 0.096 | H-atom parameters constrained |
S = 1.08 | Δρmax = 0.78 e Å−3 |
12332 reflections | Δρmin = −0.69 e Å−3 |
595 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 | ||
C1 | 0.47872 (19) | 0.9806 (5) | 0.59090 (18) | 0.0540 (11) | |
H1 | 0.4729 | 0.8838 | 0.6039 | 0.065* | |
C2 | 0.5189 (2) | 1.0838 (6) | 0.6266 (2) | 0.0637 (13) | |
H2 | 0.5398 | 1.0577 | 0.6632 | 0.076* | |
C3 | 0.5275 (2) | 1.2265 (6) | 0.6070 (2) | 0.0676 (14) | |
H3 | 0.5550 | 1.2974 | 0.6303 | 0.081* | |
C4 | 0.4954 (2) | 1.2637 (5) | 0.5531 (2) | 0.0590 (13) | |
H4 | 0.5008 | 1.3610 | 0.5401 | 0.071* | |
C5 | 0.45500 (17) | 1.1572 (4) | 0.51770 (18) | 0.0429 (10) | |
C6 | 0.41895 (17) | 1.1804 (4) | 0.45974 (18) | 0.0425 (10) | |
C11 | 0.38240 (17) | 1.0550 (4) | 0.43218 (16) | 0.0400 (9) | |
C12 | 0.33523 (17) | 0.5711 (5) | 0.47067 (16) | 0.0421 (9) | |
C13 | 0.25652 (19) | 0.3891 (5) | 0.41511 (17) | 0.0503 (11) | |
H13A | 0.2655 | 0.2870 | 0.4044 | 0.060* | |
H13B | 0.2527 | 0.4626 | 0.3863 | 0.060* | |
C14 | 0.19769 (18) | 0.3824 (5) | 0.42284 (18) | 0.0536 (11) | |
H14A | 0.1658 | 0.3430 | 0.3898 | 0.064* | |
H14B | 0.1865 | 0.4867 | 0.4296 | 0.064* | |
C15 | 0.2039 (2) | 0.2771 (6) | 0.47048 (19) | 0.0656 (14) | |
H15A | 0.1670 | 0.2814 | 0.4768 | 0.079* | |
H15B | 0.2097 | 0.1701 | 0.4616 | 0.079* | |
C16 | 0.25689 (19) | 0.3259 (5) | 0.52196 (18) | 0.0550 (12) | |
H16A | 0.2486 | 0.4275 | 0.5336 | 0.066* | |
H16B | 0.2618 | 0.2515 | 0.5509 | 0.066* | |
C17 | 0.31480 (18) | 0.3338 (5) | 0.51270 (18) | 0.0515 (11) | |
H17A | 0.3474 | 0.3730 | 0.5453 | 0.062* | |
H17B | 0.3258 | 0.2301 | 0.5051 | 0.062* | |
N1 | 0.44742 (14) | 1.0153 (4) | 0.53759 (14) | 0.0460 (8) | |
N2 | 0.30608 (14) | 0.4380 (4) | 0.46629 (13) | 0.0445 (8) | |
S1 | 0.39245 (5) | 0.63462 (13) | 0.53043 (5) | 0.0510 (3) | |
S2 | 0.31981 (5) | 0.70232 (13) | 0.41777 (4) | 0.0500 (3) | |
Pd1 | 0.38867 (2) | 0.86906 (3) | 0.48024 (2) | 0.04174 (9) | |
C42 | −0.1449 (3) | 0.3674 (7) | 0.1333 (2) | 0.0747 (15) | |
H42 | −0.1863 | 0.3804 | 0.1138 | 0.090* | |
C43 | −0.1223 (3) | 0.2369 (7) | 0.1647 (2) | 0.0768 (16) | |
H43 | −0.1487 | 0.1610 | 0.1674 | 0.092* | |
C44 | −0.0605 (3) | 0.2182 (6) | 0.1925 (2) | 0.0716 (15) | |
H44 | −0.0453 | 0.1289 | 0.2134 | 0.086* | |
C45 | −0.0210 (2) | 0.3326 (5) | 0.18941 (18) | 0.0532 (12) | |
C46 | 0.0450 (2) | 0.3269 (5) | 0.21499 (18) | 0.0535 (11) | |
C47 | 0.0774 (3) | 0.2004 (6) | 0.2458 (2) | 0.0753 (16) | |
H47 | 0.0571 | 0.1136 | 0.2510 | 0.090* | |
C48 | 0.1401 (3) | 0.2049 (7) | 0.2685 (2) | 0.0793 (17) | |
H48 | 0.1618 | 0.1208 | 0.2891 | 0.095* | |
C49 | 0.1703 (3) | 0.3323 (6) | 0.2609 (2) | 0.0709 (14) | |
H49 | 0.2124 | 0.3349 | 0.2766 | 0.085* | |
C50 | 0.1381 (2) | 0.4575 (5) | 0.22969 (18) | 0.0571 (12) | |
H50 | 0.1589 | 0.5429 | 0.2244 | 0.068* | |
C51 | 0.0755 (2) | 0.4574 (5) | 0.20639 (17) | 0.0473 (10) | |
C52 | 0.03404 (18) | 0.9253 (5) | 0.12234 (16) | 0.0453 (10) | |
C53 | 0.10411 (19) | 1.1262 (5) | 0.11693 (18) | 0.0578 (12) | |
H53A | 0.1342 | 1.0456 | 0.1335 | 0.069* | |
H53B | 0.1119 | 1.2115 | 0.1428 | 0.069* | |
C54 | 0.1088 (2) | 1.1846 (6) | 0.06519 (19) | 0.0626 (13) | |
H54A | 0.1483 | 1.2317 | 0.0743 | 0.075* | |
H54B | 0.1052 | 1.0970 | 0.0410 | 0.075* | |
C55 | 0.0602 (2) | 1.3033 (6) | 0.0360 (2) | 0.0693 (14) | |
H55A | 0.0657 | 1.3951 | 0.0588 | 0.083* | |
H55B | 0.0633 | 1.3352 | 0.0023 | 0.083* | |
C56 | −0.0014 (2) | 1.2336 (5) | 0.02334 (19) | 0.0635 (13) | |
H56A | −0.0086 | 1.1498 | −0.0030 | 0.076* | |
H56B | −0.0322 | 1.3129 | 0.0070 | 0.076* | |
C57 | −0.0066 (2) | 1.1706 (5) | 0.07404 (19) | 0.0575 (12) | |
H57A | −0.0061 | 1.2570 | 0.0978 | 0.069* | |
H57B | −0.0450 | 1.1167 | 0.0638 | 0.069* | |
N5 | −0.04432 (17) | 0.4636 (4) | 0.15885 (15) | 0.0528 (9) | |
N6 | 0.04299 (15) | 1.0624 (4) | 0.10399 (14) | 0.0467 (8) | |
S5 | 0.09201 (5) | 0.80207 (14) | 0.16127 (5) | 0.0576 (3) | |
S6 | −0.03610 (5) | 0.84672 (14) | 0.10983 (5) | 0.0585 (3) | |
Pd3 | 0.02011 (2) | 0.62500 (4) | 0.16033 (2) | 0.04749 (10) | |
C7 | 0.4200 (2) | 1.3170 (5) | 0.4314 (2) | 0.0562 (12) | |
H7 | 0.4442 | 1.4006 | 0.4497 | 0.067* | |
C8 | 0.3848 (2) | 1.3272 (5) | 0.3759 (2) | 0.0625 (13) | |
H8 | 0.3849 | 1.4186 | 0.3571 | 0.075* | |
C9 | 0.3500 (2) | 1.2038 (6) | 0.3487 (2) | 0.0606 (13) | |
H9 | 0.3272 | 1.2102 | 0.3112 | 0.073* | |
C10 | 0.3488 (2) | 1.0690 (5) | 0.37684 (18) | 0.0545 (11) | |
H10 | 0.3248 | 0.9857 | 0.3579 | 0.065* | |
C21 | 0.4498 (2) | 0.0167 (6) | 0.1723 (2) | 0.0633 (13) | |
H21 | 0.4504 | 0.1109 | 0.1551 | 0.076* | |
C22 | 0.4939 (2) | −0.0922 (7) | 0.1785 (2) | 0.0749 (15) | |
H22 | 0.5235 | −0.0731 | 0.1652 | 0.090* | |
C23 | 0.4934 (3) | −0.2304 (7) | 0.2049 (2) | 0.0777 (16) | |
H23 | 0.5239 | −0.3039 | 0.2109 | 0.093* | |
C24 | 0.4481 (2) | −0.2592 (6) | 0.22206 (19) | 0.0699 (15) | |
H24 | 0.4470 | −0.3541 | 0.2386 | 0.084* | |
C25 | 0.4037 (2) | −0.1475 (5) | 0.21495 (17) | 0.0544 (12) | |
C26 | 0.3526 (2) | −0.1629 (5) | 0.23108 (17) | 0.0529 (12) | |
C27 | 0.3415 (2) | −0.2961 (6) | 0.25529 (19) | 0.0652 (14) | |
H27 | 0.3670 | −0.3822 | 0.2620 | 0.078* | |
C28 | 0.2925 (3) | −0.2998 (6) | 0.26931 (19) | 0.0723 (16) | |
H28 | 0.2856 | −0.3882 | 0.2863 | 0.087* | |
C29 | 0.2534 (2) | −0.1751 (6) | 0.25874 (19) | 0.0689 (14) | |
H29 | 0.2200 | −0.1791 | 0.2680 | 0.083* | |
C30 | 0.2648 (2) | −0.0418 (5) | 0.23374 (17) | 0.0584 (12) | |
H30 | 0.2385 | 0.0428 | 0.2264 | 0.070* | |
C31 | 0.3136 (2) | −0.0332 (5) | 0.21989 (16) | 0.0488 (11) | |
C32 | 0.29763 (19) | 0.4484 (5) | 0.14680 (16) | 0.0474 (10) | |
C33 | 0.2954 (2) | 0.6764 (5) | 0.09022 (18) | 0.0541 (11) | |
H33A | 0.3330 | 0.6322 | 0.0912 | 0.065* | |
H33B | 0.3037 | 0.7812 | 0.1052 | 0.065* | |
C34 | 0.2494 (2) | 0.6829 (6) | 0.03194 (18) | 0.0614 (13) | |
H34A | 0.2450 | 0.5797 | 0.0158 | 0.074* | |
H34B | 0.2637 | 0.7530 | 0.0111 | 0.074* | |
C35 | 0.1882 (2) | 0.7388 (6) | 0.0286 (2) | 0.0720 (15) | |
H35A | 0.1910 | 0.8477 | 0.0395 | 0.086* | |
H35B | 0.1587 | 0.7308 | −0.0088 | 0.086* | |
C36 | 0.1675 (2) | 0.6421 (6) | 0.06549 (18) | 0.0614 (13) | |
H36A | 0.1306 | 0.6868 | 0.0658 | 0.074* | |
H36B | 0.1584 | 0.5368 | 0.0511 | 0.074* | |
C37 | 0.2145 (2) | 0.6357 (5) | 0.12260 (18) | 0.0584 (12) | |
H37A | 0.2199 | 0.7390 | 0.1388 | 0.070* | |
H37B | 0.2011 | 0.5662 | 0.1443 | 0.070* | |
C41 | −0.1044 (2) | 0.4787 (6) | 0.1314 (2) | 0.0636 (13) | |
H41 | −0.1193 | 0.5677 | 0.1102 | 0.076* | |
N3 | 0.40623 (16) | −0.0083 (4) | 0.19014 (14) | 0.0527 (9) | |
N4 | 0.27226 (16) | 0.5801 (4) | 0.12316 (14) | 0.0499 (9) | |
S3 | 0.36489 (5) | 0.37714 (14) | 0.14774 (5) | 0.0570 (3) | |
S4 | 0.26594 (6) | 0.32525 (13) | 0.17964 (5) | 0.0571 (3) | |
Pd2 | 0.34020 (2) | 0.14795 (4) | 0.18645 (2) | 0.04822 (10) |
U11 | U22 | U33 | U12 | U13 | U23 | |
C1 | 0.057 (3) | 0.058 (3) | 0.044 (3) | −0.006 (2) | 0.018 (2) | −0.005 (2) |
C2 | 0.059 (3) | 0.078 (3) | 0.049 (3) | −0.005 (3) | 0.016 (2) | −0.020 (3) |
C3 | 0.051 (3) | 0.074 (4) | 0.069 (4) | −0.015 (3) | 0.016 (3) | −0.030 (3) |
C4 | 0.053 (3) | 0.047 (3) | 0.078 (4) | −0.011 (2) | 0.027 (3) | −0.015 (3) |
C5 | 0.037 (2) | 0.040 (2) | 0.056 (3) | −0.0019 (19) | 0.023 (2) | −0.008 (2) |
C6 | 0.038 (2) | 0.038 (2) | 0.057 (3) | 0.0010 (18) | 0.026 (2) | −0.003 (2) |
C11 | 0.037 (2) | 0.040 (2) | 0.045 (3) | 0.0036 (18) | 0.0189 (19) | −0.0031 (19) |
C12 | 0.040 (2) | 0.044 (2) | 0.046 (2) | −0.0016 (19) | 0.0220 (19) | −0.0047 (19) |
C13 | 0.056 (3) | 0.049 (2) | 0.045 (3) | −0.016 (2) | 0.020 (2) | −0.010 (2) |
C14 | 0.039 (2) | 0.067 (3) | 0.052 (3) | −0.007 (2) | 0.015 (2) | 0.005 (2) |
C15 | 0.046 (3) | 0.082 (3) | 0.069 (3) | −0.009 (3) | 0.022 (2) | 0.014 (3) |
C16 | 0.056 (3) | 0.056 (3) | 0.055 (3) | 0.008 (2) | 0.025 (2) | 0.016 (2) |
C17 | 0.047 (3) | 0.049 (2) | 0.056 (3) | −0.002 (2) | 0.017 (2) | 0.010 (2) |
N1 | 0.0406 (19) | 0.050 (2) | 0.049 (2) | −0.0007 (16) | 0.0192 (17) | −0.0078 (17) |
N2 | 0.044 (2) | 0.0458 (19) | 0.045 (2) | −0.0068 (17) | 0.0192 (16) | 0.0000 (17) |
S1 | 0.0469 (6) | 0.0522 (6) | 0.0465 (6) | −0.0083 (5) | 0.0108 (5) | −0.0018 (5) |
S2 | 0.0547 (7) | 0.0481 (6) | 0.0446 (6) | −0.0095 (5) | 0.0170 (5) | 0.0023 (5) |
Pd1 | 0.04080 (18) | 0.03782 (16) | 0.04519 (19) | −0.00455 (14) | 0.01567 (14) | −0.00407 (15) |
C42 | 0.073 (4) | 0.083 (4) | 0.074 (4) | −0.025 (3) | 0.036 (3) | −0.020 (3) |
C43 | 0.095 (5) | 0.073 (4) | 0.077 (4) | −0.036 (3) | 0.050 (4) | −0.017 (3) |
C44 | 0.101 (5) | 0.063 (3) | 0.060 (3) | −0.019 (3) | 0.042 (3) | 0.002 (3) |
C45 | 0.083 (4) | 0.048 (3) | 0.042 (3) | −0.007 (2) | 0.039 (3) | −0.005 (2) |
C46 | 0.075 (3) | 0.053 (3) | 0.041 (3) | 0.007 (2) | 0.032 (2) | 0.003 (2) |
C47 | 0.106 (5) | 0.068 (3) | 0.066 (4) | 0.008 (3) | 0.049 (3) | 0.020 (3) |
C48 | 0.102 (5) | 0.083 (4) | 0.057 (3) | 0.030 (4) | 0.036 (3) | 0.026 (3) |
C49 | 0.079 (4) | 0.081 (4) | 0.056 (3) | 0.014 (3) | 0.031 (3) | 0.004 (3) |
C50 | 0.067 (3) | 0.056 (3) | 0.052 (3) | 0.004 (3) | 0.028 (2) | −0.001 (2) |
C51 | 0.062 (3) | 0.043 (2) | 0.044 (3) | −0.002 (2) | 0.029 (2) | −0.006 (2) |
C52 | 0.047 (2) | 0.052 (2) | 0.042 (2) | 0.001 (2) | 0.024 (2) | 0.000 (2) |
C53 | 0.049 (3) | 0.061 (3) | 0.059 (3) | −0.011 (2) | 0.016 (2) | 0.002 (2) |
C54 | 0.058 (3) | 0.072 (3) | 0.062 (3) | −0.022 (3) | 0.029 (3) | −0.003 (3) |
C55 | 0.084 (4) | 0.066 (3) | 0.058 (3) | −0.018 (3) | 0.028 (3) | 0.013 (3) |
C56 | 0.071 (3) | 0.055 (3) | 0.057 (3) | 0.001 (3) | 0.018 (3) | 0.012 (2) |
C57 | 0.051 (3) | 0.054 (3) | 0.066 (3) | 0.004 (2) | 0.022 (2) | 0.008 (2) |
N5 | 0.066 (3) | 0.050 (2) | 0.052 (2) | −0.006 (2) | 0.033 (2) | −0.0086 (19) |
N6 | 0.040 (2) | 0.050 (2) | 0.050 (2) | −0.0003 (17) | 0.0174 (16) | 0.0075 (18) |
S5 | 0.0478 (7) | 0.0572 (7) | 0.0656 (8) | 0.0043 (6) | 0.0202 (6) | 0.0132 (6) |
S6 | 0.0443 (6) | 0.0604 (7) | 0.0729 (8) | −0.0049 (6) | 0.0255 (6) | 0.0081 (6) |
Pd3 | 0.0554 (2) | 0.04311 (18) | 0.0490 (2) | −0.00138 (16) | 0.02612 (16) | −0.00015 (16) |
C7 | 0.053 (3) | 0.045 (2) | 0.073 (4) | −0.004 (2) | 0.028 (3) | 0.001 (2) |
C8 | 0.071 (3) | 0.052 (3) | 0.073 (4) | 0.010 (3) | 0.039 (3) | 0.017 (3) |
C9 | 0.068 (3) | 0.063 (3) | 0.054 (3) | 0.014 (3) | 0.027 (3) | 0.009 (3) |
C10 | 0.060 (3) | 0.048 (2) | 0.052 (3) | 0.005 (2) | 0.019 (2) | −0.002 (2) |
C21 | 0.052 (3) | 0.065 (3) | 0.065 (3) | −0.006 (3) | 0.015 (3) | −0.009 (3) |
C22 | 0.056 (3) | 0.091 (4) | 0.068 (4) | 0.003 (3) | 0.015 (3) | −0.020 (3) |
C23 | 0.069 (4) | 0.080 (4) | 0.066 (4) | 0.024 (3) | 0.007 (3) | −0.013 (3) |
C24 | 0.077 (4) | 0.057 (3) | 0.051 (3) | 0.013 (3) | 0.000 (3) | 0.001 (2) |
C25 | 0.059 (3) | 0.047 (2) | 0.037 (2) | −0.001 (2) | −0.003 (2) | −0.003 (2) |
C26 | 0.058 (3) | 0.052 (3) | 0.032 (2) | −0.007 (2) | 0.000 (2) | −0.003 (2) |
C27 | 0.073 (4) | 0.055 (3) | 0.047 (3) | −0.005 (3) | 0.002 (3) | 0.002 (2) |
C28 | 0.094 (4) | 0.061 (3) | 0.042 (3) | −0.020 (3) | 0.006 (3) | 0.004 (2) |
C29 | 0.075 (4) | 0.079 (4) | 0.047 (3) | −0.026 (3) | 0.017 (3) | −0.008 (3) |
C30 | 0.063 (3) | 0.059 (3) | 0.043 (3) | −0.011 (2) | 0.010 (2) | −0.008 (2) |
C31 | 0.049 (3) | 0.051 (3) | 0.032 (2) | −0.006 (2) | 0.002 (2) | −0.004 (2) |
C32 | 0.052 (3) | 0.049 (2) | 0.035 (2) | −0.003 (2) | 0.011 (2) | −0.004 (2) |
C33 | 0.054 (3) | 0.051 (3) | 0.056 (3) | −0.008 (2) | 0.021 (2) | 0.004 (2) |
C34 | 0.072 (3) | 0.065 (3) | 0.047 (3) | −0.014 (3) | 0.024 (2) | 0.008 (2) |
C35 | 0.062 (3) | 0.083 (4) | 0.057 (3) | −0.007 (3) | 0.009 (3) | 0.022 (3) |
C36 | 0.053 (3) | 0.070 (3) | 0.058 (3) | −0.004 (3) | 0.019 (2) | 0.001 (3) |
C37 | 0.065 (3) | 0.059 (3) | 0.058 (3) | 0.013 (2) | 0.031 (2) | 0.010 (2) |
C41 | 0.061 (3) | 0.065 (3) | 0.065 (3) | −0.004 (3) | 0.026 (3) | −0.006 (3) |
N3 | 0.049 (2) | 0.054 (2) | 0.042 (2) | −0.0057 (18) | 0.0042 (18) | −0.0072 (18) |
N4 | 0.051 (2) | 0.055 (2) | 0.044 (2) | 0.0026 (18) | 0.0195 (18) | 0.0077 (18) |
S3 | 0.0483 (7) | 0.0545 (7) | 0.0648 (8) | 0.0017 (6) | 0.0189 (6) | 0.0004 (6) |
S4 | 0.0644 (8) | 0.0543 (7) | 0.0540 (7) | 0.0005 (6) | 0.0251 (6) | 0.0104 (6) |
Pd2 | 0.0496 (2) | 0.04335 (18) | 0.0424 (2) | −0.00218 (16) | 0.00854 (15) | −0.00136 (15) |
C1—N1 | 1.351 (5) | C54—H54B | 0.9700 |
C1—C2 | 1.374 (6) | C55—C56 | 1.506 (6) |
C1—H1 | 0.9300 | C55—H55A | 0.9700 |
C2—C3 | 1.377 (7) | C55—H55B | 0.9700 |
C2—H2 | 0.9300 | C56—C57 | 1.508 (6) |
C3—C4 | 1.371 (6) | C56—H56A | 0.9700 |
C3—H3 | 0.9300 | C56—H56B | 0.9700 |
C4—C5 | 1.392 (5) | C57—N6 | 1.470 (5) |
C4—H4 | 0.9300 | C57—H57A | 0.9700 |
C5—N1 | 1.366 (5) | C57—H57B | 0.9700 |
C5—C6 | 1.454 (6) | N5—C41 | 1.342 (5) |
C6—C11 | 1.397 (5) | N5—Pd3 | 2.065 (4) |
C6—C7 | 1.398 (6) | S5—Pd3 | 2.2935 (12) |
C11—C10 | 1.377 (5) | S6—Pd3 | 2.4069 (12) |
C11—Pd1 | 2.011 (4) | C7—C8 | 1.384 (6) |
C12—N2 | 1.319 (5) | C7—H7 | 0.9300 |
C12—S2 | 1.725 (4) | C8—C9 | 1.363 (6) |
C12—S1 | 1.727 (4) | C8—H8 | 0.9300 |
C13—N2 | 1.471 (5) | C9—C10 | 1.383 (6) |
C13—C14 | 1.512 (5) | C9—H9 | 0.9300 |
C13—H13A | 0.9700 | C10—H10 | 0.9300 |
C13—H13B | 0.9700 | C21—N3 | 1.331 (6) |
C14—C15 | 1.516 (6) | C21—C22 | 1.372 (6) |
C14—H14A | 0.9700 | C21—H21 | 0.9300 |
C14—H14B | 0.9700 | C22—C23 | 1.378 (7) |
C15—C16 | 1.513 (6) | C22—H22 | 0.9300 |
C15—H15A | 0.9700 | C23—C24 | 1.364 (7) |
C15—H15B | 0.9700 | C23—H23 | 0.9300 |
C16—C17 | 1.512 (6) | C24—C25 | 1.390 (6) |
C16—H16A | 0.9700 | C24—H24 | 0.9300 |
C16—H16B | 0.9700 | C25—N3 | 1.376 (5) |
C17—N2 | 1.471 (5) | C25—C26 | 1.461 (6) |
C17—H17A | 0.9700 | C26—C27 | 1.388 (6) |
C17—H17B | 0.9700 | C26—C31 | 1.408 (6) |
N1—Pd1 | 2.045 (3) | C27—C28 | 1.374 (7) |
S1—Pd1 | 2.3939 (11) | C27—H27 | 0.9300 |
S2—Pd1 | 2.3149 (11) | C28—C29 | 1.376 (7) |
C42—C43 | 1.373 (7) | C28—H28 | 0.9300 |
C42—C41 | 1.378 (6) | C29—C30 | 1.403 (6) |
C42—H42 | 0.9300 | C29—H29 | 0.9300 |
C43—C44 | 1.382 (7) | C30—C31 | 1.368 (6) |
C43—H43 | 0.9300 | C30—H30 | 0.9300 |
C44—C45 | 1.390 (6) | C31—Pd2 | 2.016 (4) |
C44—H44 | 0.9300 | C32—N4 | 1.317 (5) |
C45—N5 | 1.368 (5) | C32—S3 | 1.721 (4) |
C45—C46 | 1.459 (6) | C32—S4 | 1.730 (4) |
C46—C47 | 1.395 (6) | C33—N4 | 1.467 (5) |
C46—C51 | 1.405 (6) | C33—C34 | 1.508 (6) |
C47—C48 | 1.384 (7) | C33—H33A | 0.9700 |
C47—H47 | 0.9300 | C33—H33B | 0.9700 |
C48—C49 | 1.371 (7) | C34—C35 | 1.517 (6) |
C48—H48 | 0.9300 | C34—H34A | 0.9700 |
C49—C50 | 1.388 (6) | C34—H34B | 0.9700 |
C49—H49 | 0.9300 | C35—C36 | 1.514 (6) |
C50—C51 | 1.382 (6) | C35—H35A | 0.9700 |
C50—H50 | 0.9300 | C35—H35B | 0.9700 |
C51—Pd3 | 2.009 (4) | C36—C37 | 1.494 (6) |
C52—N6 | 1.322 (5) | C36—H36A | 0.9700 |
C52—S6 | 1.722 (4) | C36—H36B | 0.9700 |
C52—S5 | 1.727 (4) | C37—N4 | 1.464 (5) |
C53—N6 | 1.476 (5) | C37—H37A | 0.9700 |
C53—C54 | 1.515 (6) | C37—H37B | 0.9700 |
C53—H53A | 0.9700 | C41—H41 | 0.9300 |
C53—H53B | 0.9700 | N3—Pd2 | 2.050 (4) |
C54—C55 | 1.511 (6) | S3—Pd2 | 2.3996 (12) |
C54—H54A | 0.9700 | S4—Pd2 | 2.2963 (13) |
N1—C1—C2 | 122.1 (4) | C55—C56—H56A | 109.3 |
N1—C1—H1 | 118.9 | C57—C56—H56A | 109.3 |
C2—C1—H1 | 118.9 | C55—C56—H56B | 109.3 |
C1—C2—C3 | 118.6 (5) | C57—C56—H56B | 109.3 |
C1—C2—H2 | 120.7 | H56A—C56—H56B | 108.0 |
C3—C2—H2 | 120.7 | N6—C57—C56 | 111.9 (4) |
C4—C3—C2 | 119.8 (5) | N6—C57—H57A | 109.2 |
C4—C3—H3 | 120.1 | C56—C57—H57A | 109.2 |
C2—C3—H3 | 120.1 | N6—C57—H57B | 109.2 |
C3—C4—C5 | 120.5 (4) | C56—C57—H57B | 109.2 |
C3—C4—H4 | 119.7 | H57A—C57—H57B | 107.9 |
C5—C4—H4 | 119.7 | C41—N5—C45 | 120.1 (4) |
N1—C5—C4 | 119.0 (4) | C41—N5—Pd3 | 125.7 (3) |
N1—C5—C6 | 114.8 (3) | C45—N5—Pd3 | 114.2 (3) |
C4—C5—C6 | 126.2 (4) | C52—N6—C57 | 122.9 (3) |
C11—C6—C7 | 120.1 (4) | C52—N6—C53 | 122.4 (4) |
C11—C6—C5 | 116.0 (4) | C57—N6—C53 | 114.4 (3) |
C7—C6—C5 | 123.9 (4) | C52—S5—Pd3 | 88.37 (15) |
C10—C11—C6 | 118.4 (4) | C52—S6—Pd3 | 84.87 (14) |
C10—C11—Pd1 | 128.0 (3) | C51—Pd3—N5 | 81.04 (16) |
C6—C11—Pd1 | 113.6 (3) | C51—Pd3—S5 | 98.70 (13) |
N2—C12—S2 | 123.9 (3) | N5—Pd3—S5 | 179.26 (10) |
N2—C12—S1 | 123.7 (3) | C51—Pd3—S6 | 173.14 (13) |
S2—C12—S1 | 112.5 (2) | N5—Pd3—S6 | 105.44 (11) |
N2—C13—C14 | 110.0 (3) | S5—Pd3—S6 | 74.84 (4) |
N2—C13—H13A | 109.7 | C8—C7—C6 | 119.7 (4) |
C14—C13—H13A | 109.7 | C8—C7—H7 | 120.1 |
N2—C13—H13B | 109.7 | C6—C7—H7 | 120.1 |
C14—C13—H13B | 109.7 | C9—C8—C7 | 120.3 (4) |
H13A—C13—H13B | 108.2 | C9—C8—H8 | 119.8 |
C13—C14—C15 | 110.6 (4) | C7—C8—H8 | 119.8 |
C13—C14—H14A | 109.5 | C8—C9—C10 | 119.9 (5) |
C15—C14—H14A | 109.5 | C8—C9—H9 | 120.1 |
C13—C14—H14B | 109.5 | C10—C9—H9 | 120.1 |
C15—C14—H14B | 109.5 | C11—C10—C9 | 121.6 (4) |
H14A—C14—H14B | 108.1 | C11—C10—H10 | 119.2 |
C16—C15—C14 | 111.3 (4) | C9—C10—H10 | 119.2 |
C16—C15—H15A | 109.4 | N3—C21—C22 | 122.0 (5) |
C14—C15—H15A | 109.4 | N3—C21—H21 | 119.0 |
C16—C15—H15B | 109.4 | C22—C21—H21 | 119.0 |
C14—C15—H15B | 109.4 | C21—C22—C23 | 118.8 (5) |
H15A—C15—H15B | 108.0 | C21—C22—H22 | 120.6 |
C17—C16—C15 | 111.2 (4) | C23—C22—H22 | 120.6 |
C17—C16—H16A | 109.4 | C24—C23—C22 | 119.8 (5) |
C15—C16—H16A | 109.4 | C24—C23—H23 | 120.1 |
C17—C16—H16B | 109.4 | C22—C23—H23 | 120.1 |
C15—C16—H16B | 109.4 | C23—C24—C25 | 120.3 (5) |
H16A—C16—H16B | 108.0 | C23—C24—H24 | 119.8 |
N2—C17—C16 | 109.5 (3) | C25—C24—H24 | 119.8 |
N2—C17—H17A | 109.8 | N3—C25—C24 | 118.8 (5) |
C16—C17—H17A | 109.8 | N3—C25—C26 | 115.1 (4) |
N2—C17—H17B | 109.8 | C24—C25—C26 | 126.1 (5) |
C16—C17—H17B | 109.8 | C27—C26—C31 | 120.7 (5) |
H17A—C17—H17B | 108.2 | C27—C26—C25 | 123.6 (5) |
C1—N1—C5 | 120.0 (4) | C31—C26—C25 | 115.8 (4) |
C1—N1—Pd1 | 125.6 (3) | C28—C27—C26 | 119.5 (5) |
C5—N1—Pd1 | 114.4 (3) | C28—C27—H27 | 120.2 |
C12—N2—C13 | 122.3 (3) | C26—C27—H27 | 120.2 |
C12—N2—C17 | 123.8 (3) | C27—C28—C29 | 121.2 (5) |
C13—N2—C17 | 113.6 (3) | C27—C28—H28 | 119.4 |
C12—S1—Pd1 | 84.79 (14) | C29—C28—H28 | 119.4 |
C12—S2—Pd1 | 87.34 (14) | C28—C29—C30 | 118.7 (5) |
C11—Pd1—N1 | 81.17 (15) | C28—C29—H29 | 120.6 |
C11—Pd1—S2 | 100.29 (12) | C30—C29—H29 | 120.6 |
N1—Pd1—S2 | 177.45 (10) | C31—C30—C29 | 121.7 (5) |
C11—Pd1—S1 | 175.08 (12) | C31—C30—H30 | 119.2 |
N1—Pd1—S1 | 103.52 (10) | C29—C30—H30 | 119.2 |
S2—Pd1—S1 | 75.09 (4) | C30—C31—C26 | 118.2 (4) |
C43—C42—C41 | 118.2 (5) | C30—C31—Pd2 | 128.3 (4) |
C43—C42—H42 | 120.9 | C26—C31—Pd2 | 113.4 (3) |
C41—C42—H42 | 120.9 | N4—C32—S3 | 124.3 (3) |
C42—C43—C44 | 120.0 (5) | N4—C32—S4 | 123.4 (3) |
C42—C43—H43 | 120.0 | S3—C32—S4 | 112.3 (2) |
C44—C43—H43 | 120.0 | N4—C33—C34 | 109.9 (3) |
C43—C44—C45 | 120.1 (5) | N4—C33—H33A | 109.7 |
C43—C44—H44 | 119.9 | C34—C33—H33A | 109.7 |
C45—C44—H44 | 119.9 | N4—C33—H33B | 109.7 |
N5—C45—C44 | 119.0 (5) | C34—C33—H33B | 109.7 |
N5—C45—C46 | 114.7 (4) | H33A—C33—H33B | 108.2 |
C44—C45—C46 | 126.3 (5) | C33—C34—C35 | 111.7 (4) |
C47—C46—C51 | 120.4 (5) | C33—C34—H34A | 109.3 |
C47—C46—C45 | 123.5 (5) | C35—C34—H34A | 109.3 |
C51—C46—C45 | 116.1 (4) | C33—C34—H34B | 109.3 |
C48—C47—C46 | 119.5 (5) | C35—C34—H34B | 109.3 |
C48—C47—H47 | 120.2 | H34A—C34—H34B | 107.9 |
C46—C47—H47 | 120.2 | C36—C35—C34 | 110.7 (4) |
C49—C48—C47 | 120.6 (5) | C36—C35—H35A | 109.5 |
C49—C48—H48 | 119.7 | C34—C35—H35A | 109.5 |
C47—C48—H48 | 119.7 | C36—C35—H35B | 109.5 |
C48—C49—C50 | 119.9 (5) | C34—C35—H35B | 109.5 |
C48—C49—H49 | 120.0 | H35A—C35—H35B | 108.1 |
C50—C49—H49 | 120.0 | C37—C36—C35 | 111.8 (4) |
C51—C50—C49 | 121.2 (5) | C37—C36—H36A | 109.3 |
C51—C50—H50 | 119.4 | C35—C36—H36A | 109.3 |
C49—C50—H50 | 119.4 | C37—C36—H36B | 109.3 |
C50—C51—C46 | 118.3 (4) | C35—C36—H36B | 109.3 |
C50—C51—Pd3 | 127.8 (3) | H36A—C36—H36B | 107.9 |
C46—C51—Pd3 | 113.9 (3) | N4—C37—C36 | 110.6 (4) |
N6—C52—S6 | 124.5 (3) | N4—C37—H37A | 109.5 |
N6—C52—S5 | 123.6 (3) | C36—C37—H37A | 109.5 |
S6—C52—S5 | 111.9 (2) | N4—C37—H37B | 109.5 |
N6—C53—C54 | 109.8 (4) | C36—C37—H37B | 109.5 |
N6—C53—H53A | 109.7 | H37A—C37—H37B | 108.1 |
C54—C53—H53A | 109.7 | N5—C41—C42 | 122.5 (5) |
N6—C53—H53B | 109.7 | N5—C41—H41 | 118.8 |
C54—C53—H53B | 109.7 | C42—C41—H41 | 118.8 |
H53A—C53—H53B | 108.2 | C21—N3—C25 | 120.3 (4) |
C55—C54—C53 | 111.6 (4) | C21—N3—Pd2 | 125.8 (3) |
C55—C54—H54A | 109.3 | C25—N3—Pd2 | 113.9 (3) |
C53—C54—H54A | 109.3 | C32—N4—C37 | 122.7 (4) |
C55—C54—H54B | 109.3 | C32—N4—C33 | 123.6 (4) |
C53—C54—H54B | 109.3 | C37—N4—C33 | 113.4 (3) |
H54A—C54—H54B | 108.0 | C32—S3—Pd2 | 84.42 (15) |
C56—C55—C54 | 109.9 (4) | C32—S4—Pd2 | 87.47 (15) |
C56—C55—H55A | 109.7 | C31—Pd2—N3 | 81.62 (17) |
C54—C55—H55A | 109.7 | C31—Pd2—S4 | 99.70 (14) |
C56—C55—H55B | 109.7 | N3—Pd2—S4 | 178.20 (11) |
C54—C55—H55B | 109.7 | C31—Pd2—S3 | 174.86 (14) |
H55A—C55—H55B | 108.2 | N3—Pd2—S3 | 103.49 (11) |
C55—C56—C57 | 111.6 (4) | S4—Pd2—S3 | 75.20 (4) |
Experimental details
Crystal data | |
Chemical formula | [Pd(C11H8N)(C6H10NS2)] |
Mr | 420.85 |
Crystal system, space group | Monoclinic, P21/c |
Temperature (K) | 293 |
a, b, c (Å) | 24.0780 (9), 8.5585 (2), 26.6841 (10) |
β (°) | 113.514 (4) |
V (Å3) | 5042.2 (3) |
Z | 12 |
Radiation type | Mo Kα |
µ (mm−1) | 1.35 |
Crystal size (mm) | 0.25 × 0.15 × 0.03 |
Data collection | |
Diffractometer | Agilent Xcalibur Sapphire3 |
Absorption correction | Multi-scan (CrysAlis PRO; Agilent, 2011) |
Tmin, Tmax | 0.604, 1.000 |
No. of measured, independent and observed [I > 2σ(I)] reflections | 58403, 12332, 8246 |
Rint | 0.057 |
(sin θ/λ)max (Å−1) | 0.684 |
Refinement | |
R[F2 > 2σ(F2)], wR(F2), S | 0.052, 0.096, 1.08 |
No. of reflections | 12332 |
No. of parameters | 595 |
H-atom treatment | H-atom parameters constrained |
Δρmax, Δρmin (e Å−3) | 0.78, −0.69 |
Computer programs: CrysAlis PRO (Agilent, 2011), SIR92 (Altomare et al., 1994), SHELXL2014 (Sheldrick, 2008), CrystalMaker (CrystalMaker, 2011).
Acknowledgements
Financial support from the Swedish Research Council and the Knut and Alice Wallenberg Foundation is gratefully acknowledged.
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