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Acta Cryst. (2007). E63, m1718-m1719    [ doi:10.1107/S1600536807023173 ]

cis-Dichloridobis{[(S)-N-(3,5-dioxa-4-phosphacyclohepta[2,1-a;3,4-a']dinaphthalen-4-yl]dibenz[b,f]azepin-[kappa]P}palladium(II) deuterochloroform disolvate

A. Briceño and R. Dorta

Abstract top

The chiral bidentate P-olefin ligand (S)-(3,5-dioxa-4-phosphacyclohepta[2,1-a;3,4-a']dinaphthalen-4-yl)dibenzo[b,f]azepin reacted with PdCl2(NCCH3)2 to form the title compound, [PdCl2(C34H22NO2P)2]·2CDCl3. The Pd atom displays a distorted PdCl2P2 square-planar cis geometry. The title compound forms a three-dimensional hydrogen-bonded network from supramolecular right-handed helices assembled via C-H...Cl interactions, resulting in an array of channels along the c axis filled with deuterochloroform solvent molecules.

Comment top

P-olefin ligands constitute a rather new entry in the development of efficient bidentate ligand systems for organometallic reactivity and catalysis. Grützmacher et al. developed a new class of P-olefin ligands based on the dibenzo[b,f]cycloheptene and dibenzo[b,f]azepin motifs, several of them chiral (Maire et al., 2004). On the other hand, de Vries and Feringa (Van den Berg et al., 2000) showed that chiral phosphoramidites are highly versatile monodentate ligands and so we anticipated that the dibenzo[b,f]azepin molecule could be readily used to form new chiral phosphoramidite-olefin ligands such as (I). Ligand (I) has very recently been disclosed to be an excellent ligand for the enantioselective formation of allylic amines from allylic alcohols (Defieber et al., 2007).

Here, we report the crystal structure of a Pd(II) complex bearing the chiral ligand (I). The asymmetric unit of (II) consists of one metal complex molecule and three independent deuterocloroform molecules (two of which are half occupied). The Pd atom displays a distorted square planar environment, in which two ligands (I) are coordinated through their P atoms in a monodentade fashion and the remaining coordination sites are occupied by two chloride anions. The ligands are located in a cis configuration around the metal centre [P2—Pd1—P1 = 94.59 (7)°; Cl2—Pd—Cl1 = 89.24 (9)°]. The metal complex adopts pseudo-C2 symmetry about the Pd atom (Fig. 1). The naphtyl groups are twisted in both molecules as indicated by torsion angles of 50.39 (2)° for C1—C10—C11—C12 and 52.23 (2)° for C35—C44—C45—C46.

The crystal structure of (II) consists of a three-dimensional-hydrogen bonded network, which is self assembled via C—H··· π and C—H···Cl interaction [C27i···CL2: 3.741 (12) Å and C14i···Cl2: 3.613 (10) Å; i= x, 1 - y, 1/4 + z]. The coordinated chloride (Cl2) ion causes the self-assembly of the metal complex to generate a right-handed helical arrangement along the fourfold screw axis (41). Neighbouring helices are assembled by weak van der Waals interactions to afford a 3-D hydrogen-bonded assembly. This organization yields a framework with one-dimensional channels running along the c axis, where the deuterochloroform molecules are allocated, and which are sustained into the channels by C—H···Cl hydrogen bonding to the chloride ligands of the complex [Cl1···C2Sii: 3.358 Å; ii= x, 1 - y, -3/4 + z] (Fig 2).

Related literature top

For related literature, see: Deblon et al. (2003); Defieber et al. (2007); Maire et al. (2004); Van den Berg et al. (2000).

Experimental top

Two equivalents of ligand (I) reacted cleanly with PdCl2(NCCH3)2 in toluene/acetonitrile solution to afford the title compound (II) in yields of over 90%. Single crystals of (II) were grown from a CDCl3 solution layered with Et2O. The crystals are unstable outside their mother-liquor, and a single-crystal was sealed in a Lindemann capillary for intensity collection, together with its mother-liquor.

Refinement top

All H atoms bound to carbon were included in calculated positions (C—H = 0.93–0.98 Å) and refined as riding with Uiso(H) = 1.2Ueq(C).

The dibenzoazepine framgment containing the N2 atom was found disordered over two positions. The occupational parameters were determined to be 0.70 and 0.30. The non-hydrogen atoms of the six-menbered ring of this frament were refined with the atoms being forced into planarity. The deuterochloroform molecules were also found disordered. The disorder of the C2S molecule was modelled by two sets of chlorine positions with occupancies 0.60 and 0.40. The best model for the remaining solvent molecules was obtained by free refinement of its occupation factors, giving a partial occupation of approximatly 0.5 for both molecules. These occupations were fixed during the final refinements. All C—Cl distances were restrained to similar lenghts. The absolute structure was assigned from the known configuration of the starting binaphtol reagent used in the synthesis of ligand (I) and confirmed by refinement of the Flack (1983) absolute structure parameter.

Computing details top

Data collection: CrystalClear (Rigaku/MSC Inc., 2000); cell refinement: CrystalClear; data reduction: CrystalStructure (Rigaku/MSC Inc., 2004); program(s) used to solve structure: SHELXLTL-NT (Bruker, 1998); program(s) used to refine structure: SHELXLTL-NT; molecular graphics: SHELXLTL-NT and DIAMOND (Brandenburg, 1998); software used to prepare material for publication: SHELXLTL-NT and PLATON (Spek, 2003).

Figures top
[Figure 1] Fig. 1. Molecular structure of the main molecule of (II), showing the atom-labelling scheme. Displacement ellipsoids are drawn at the 30% probability level. H atoms have been omitted for clarity.
[Figure 2] Fig. 2. View of the three-dimensional hydrogen bonded network observed in the crystal structure of (II), showing one-dimensional channels along the c axis.
[Figure 3] Fig. 3. Reaction scheme.
Dichlorido- cis-bis[{(S)-(3,5-dioxa-4-phosphacyclohepta[2,1 - a;3,4-a']dinaphthalen-4-yl)dibenz[b,f]azepin}-\kP]palladium(II) deuterochloroform disolvate top
Crystal data top
[PdCl2(C34H22NO2P)2].2CDCl3Dx = 1.377 Mg m−3
Mr = 1431.03Mo Kα radiation, λ = 0.71070 Å
Tetragonal, P41Cell parameters from 2378 reflections
Hall symbol: P 4wθ = 2.0–27.6°
a = 19.866 (2) ŵ = 0.67 mm−1
c = 17.497 (2) ÅT = 293 K
V = 6905.2 (13) Å3Prism, yellow
Z = 40.42 × 0.30 × 0.25 mm
F(000) = 2896
Data collection top
Rigaku AFC7S Mercury
diffractometer		14408 independent reflections
Radiation source: normal-focus sealed tube9124 reflections with I > 2σ(I)
graphiteRint = 0.063
Detector resolution: 14.6306 pixels mm-1θmax = 28.0°, θmin = 1.5°
ω scansh = −24→21
Absorption correction: multi-scan
Jacobson (1998)		k = −23→23
Tmin = 0.802, Tmax = 0.891l = −22→22
79958 measured reflections
Refinement top
Refinement on F2Secondary atom site location: difference Fourier map
Least-squares matrix: fullHydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.074H-atom parameters constrained
wR(F2) = 0.248 w = 1/[σ2(Fo2) + (0.1446P)2 + 3.0373P]
where P = (Fo2 + 2Fc2)/3
S = 1.07(Δ/σ)max = 0.001
14408 reflectionsΔρmax = 1.06 e Å−3
886 parametersΔρmin = −0.71 e Å−3
593 restraintsAbsolute structure: Flack (1983), with 5079 Friedel pairs
Primary atom site location: structure-invariant direct methodsFlack parameter: 0.02 (4)
Crystal data top
[PdCl2(C34H22NO2P)2].2CDCl3Z = 4
Mr = 1431.03Mo Kα radiation
Tetragonal, P41µ = 0.67 mm−1
a = 19.866 (2) ÅT = 293 K
c = 17.497 (2) Å0.42 × 0.30 × 0.25 mm
V = 6905.2 (13) Å3
Data collection top
Rigaku AFC7S Mercury
diffractometer		14408 independent reflections
Absorption correction: multi-scan
Jacobson (1998)		9124 reflections with I > 2σ(I)
Tmin = 0.802, Tmax = 0.891Rint = 0.063
79958 measured reflectionsθmax = 28.0°
Refinement top
R[F2 > 2σ(F2)] = 0.074H-atom parameters constrained
wR(F2) = 0.248Δρmax = 1.06 e Å−3
S = 1.07Δρmin = −0.71 e Å−3
14408 reflectionsAbsolute structure: Flack (1983), with 5079 Friedel pairs
886 parametersFlack parameter: 0.02 (4)
593 restraints
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.

Refinement. Refinement of F2 against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F2, conventional R-factors R are based on F, with F set to zero for negative F2. The threshold expression of F2 > σ(F2) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F2 are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/UeqOcc. (<1)
Pd10.46461 (3)0.15920 (3)0.07387 (5)0.05517 (19)
P20.51845 (11)0.13326 (10)0.18186 (12)0.0550 (5)
P10.54240 (10)0.23245 (9)0.03450 (12)0.0515 (4)
Cl20.39914 (12)0.18825 (12)−0.03184 (14)0.0767 (6)
Cl10.38606 (14)0.07551 (13)0.10470 (16)0.0870 (8)
O10.5486 (3)0.2454 (3)−0.0559 (3)0.0584 (13)
O20.6150 (2)0.2024 (2)0.0547 (3)0.0511 (12)
O40.5558 (3)0.1988 (3)0.2163 (3)0.0591 (13)
N10.5325 (3)0.3100 (3)0.0626 (4)0.0546 (15)
O30.4720 (3)0.1113 (3)0.2535 (3)0.0614 (13)
N20.5686 (4)0.0687 (3)0.1775 (4)0.0601 (16)
C10.5795 (5)0.2007 (4)−0.1058 (4)0.060 (2)
C20.5371 (5)0.1683 (5)−0.1609 (5)0.073 (2)
H2A0.49100.1760−0.16130.087*
C30.5653 (6)0.1268 (5)−0.2116 (5)0.077 (3)
H30.53850.1092−0.25030.093*
C40.6333 (6)0.1087 (5)−0.2095 (5)0.075 (2)
C50.6571 (8)0.0573 (6)−0.2551 (7)0.094 (3)
H50.62870.0364−0.28990.112*
C60.7220 (10)0.0376 (8)−0.2491 (8)0.118 (5)
H60.73760.0028−0.28000.141*
C70.7696 (7)0.0704 (6)−0.1936 (7)0.101 (4)
H70.81450.0573−0.19080.121*
C80.7454 (6)0.1190 (5)−0.1486 (6)0.081 (3)
H80.77390.1397−0.11360.098*
C90.6768 (5)0.1399 (4)−0.1532 (5)0.063 (2)
C100.6474 (4)0.1920 (4)−0.1040 (4)0.0544 (18)
C110.6907 (4)0.2292 (4)−0.0508 (4)0.0519 (17)
C120.6748 (4)0.2308 (4)0.0278 (5)0.0525 (17)
C130.7195 (4)0.2582 (4)0.0825 (5)0.0581 (18)
H130.71010.25470.13440.070*
C140.7761 (4)0.2895 (4)0.0584 (6)0.068 (2)
H140.80550.30670.09490.082*
C150.7926 (4)0.2973 (4)−0.0205 (5)0.0586 (19)
C160.8480 (5)0.3376 (6)−0.0460 (7)0.088 (3)
H160.87540.3586−0.01010.105*
C170.8612 (5)0.3456 (6)−0.1210 (7)0.089 (3)
H170.89840.3702−0.13720.106*
C180.8180 (6)0.3163 (6)−0.1731 (7)0.093 (3)
H180.82610.3228−0.22490.112*
C190.7646 (5)0.2785 (5)−0.1523 (5)0.077 (3)
H190.73800.2589−0.18980.092*
C200.7485 (4)0.2680 (4)−0.0745 (5)0.0599 (19)
C210.5706 (4)0.3648 (4)0.0274 (6)0.062 (2)
C220.5534 (5)0.3884 (5)−0.0429 (6)0.074 (2)
H220.51680.3706−0.06900.089*
C230.5926 (7)0.4409 (6)−0.0759 (8)0.103 (4)
H230.58050.4615−0.12160.123*
C240.6528 (7)0.4604 (7)−0.0339 (9)0.109 (4)
H240.68480.4874−0.05770.131*
C250.6625 (7)0.4415 (7)0.0337 (9)0.103 (4)
H250.69870.45990.06020.124*
C260.6224 (5)0.3950 (4)0.0710 (8)0.083 (3)
C270.6332 (6)0.3784 (5)0.1545 (8)0.093 (4)
H270.67740.37860.17170.111*
C280.5873 (7)0.3639 (5)0.2047 (7)0.083 (3)
H280.60200.35700.25450.100*
C290.5158 (5)0.3573 (4)0.1913 (6)0.071 (2)
C300.4712 (8)0.3774 (5)0.2496 (6)0.096 (4)
H300.48790.39600.29450.115*
C310.4029 (8)0.3694 (6)0.2403 (8)0.100 (4)
H310.37390.38370.27880.119*
C320.3770 (5)0.3413 (6)0.1763 (6)0.082 (3)
H320.33080.33510.17140.099*
C330.4200 (5)0.3218 (5)0.1183 (5)0.070 (2)
H330.40210.30320.07390.083*
C340.4880 (4)0.3293 (4)0.1245 (5)0.0581 (18)
C350.4326 (5)0.1589 (5)0.2915 (5)0.071 (2)
C360.3637 (6)0.1578 (6)0.2814 (7)0.086 (3)
H360.34390.12780.24730.104*
C370.3255 (6)0.2014 (6)0.3222 (9)0.099 (3)
H370.27880.19950.31880.119*
C380.3572 (9)0.2514 (7)0.3714 (7)0.110 (5)
C390.3148 (10)0.3015 (9)0.4059 (10)0.132 (5)
H390.26870.30150.39660.158*
C400.3424 (10)0.3484 (8)0.4520 (10)0.127 (5)
H400.31500.37920.47720.152*
C410.4097 (9)0.3507 (8)0.4613 (8)0.118 (4)
H410.42790.38420.49200.142*
C420.4522 (8)0.3057 (7)0.4274 (8)0.108 (4)
H420.49850.31000.43410.130*
C430.4255 (8)0.2510 (6)0.3809 (6)0.091 (3)
C440.4646 (6)0.2013 (4)0.3422 (5)0.077 (3)
C450.5384 (7)0.1966 (5)0.3536 (6)0.084 (3)
C460.5826 (5)0.1984 (4)0.2924 (5)0.070 (2)
C470.6528 (6)0.2003 (5)0.2969 (7)0.086 (3)
H470.67930.20510.25350.103*
C480.6815 (7)0.1945 (7)0.3696 (8)0.107 (4)
H480.72780.19810.37560.128*
C490.6400 (7)0.1831 (6)0.4341 (8)0.101 (3)
C500.6698 (11)0.1701 (9)0.5084 (11)0.142 (5)
H500.71600.16810.51720.171*
C510.6216 (11)0.1611 (10)0.5647 (12)0.149 (6)
H510.63920.15140.61270.178*
C520.5558 (10)0.1637 (8)0.5626 (11)0.136 (5)
H520.52950.15640.60580.163*
C530.5293 (9)0.1772 (7)0.4950 (6)0.115 (5)
H530.48280.18060.49040.138*
C540.5703 (8)0.1869 (5)0.4288 (6)0.096 (4)
C550.5962 (5)0.0410 (5)0.1050 (4)0.058 (2)0.695 (16)
C560.5506 (5)0.0098 (5)0.0564 (5)0.065 (3)0.695 (16)
H560.50620.00350.07180.078*0.695 (16)
C570.5713 (6)−0.0121 (5)−0.0154 (5)0.077 (3)0.695 (16)
H570.5407−0.0330−0.04790.092*0.695 (16)
C580.6376 (7)−0.0028 (6)−0.0384 (4)0.085 (4)0.695 (16)
H580.6514−0.0174−0.08640.102*0.695 (16)
C590.6832 (6)0.0285 (6)0.0103 (5)0.077 (3)0.695 (16)
H590.72760.0347−0.00510.092*0.695 (16)
C600.6625 (5)0.0503 (5)0.0820 (5)0.066 (3)0.695 (16)
C610.7128 (8)0.0813 (8)0.1411 (12)0.074 (3)0.695 (16)
H610.74650.10790.11980.089*0.695 (16)
C620.7154 (9)0.0763 (9)0.2117 (11)0.077 (3)0.695 (16)
H620.75010.09840.23730.092*0.695 (16)
C630.6679 (10)0.0385 (9)0.2562 (9)0.067 (3)0.695 (16)
C640.6964 (7)0.0089 (8)0.3205 (10)0.080 (3)0.695 (16)
H640.74240.01270.32930.096*0.695 (16)
C650.6562 (7)−0.0265 (7)0.3716 (8)0.083 (3)0.695 (16)
H650.6753−0.04630.41460.099*0.695 (16)
C660.5874 (7)−0.0322 (7)0.3585 (9)0.074 (3)0.695 (16)
H660.5605−0.05590.39270.088*0.695 (16)
C670.5589 (7)−0.0026 (8)0.2942 (11)0.066 (3)0.695 (16)
H670.5129−0.00640.28540.079*0.695 (16)
C680.5991 (10)0.0327 (10)0.2431 (9)0.061 (3)0.695 (16)
C55A0.5723 (12)0.0395 (13)0.1022 (11)0.062 (4)0.305 (16)
C56A0.5214 (11)0.0042 (13)0.0653 (13)0.059 (4)0.305 (16)
H56A0.4794−0.00020.08810.071*0.305 (16)
C57A0.5334 (14)−0.0246 (12)−0.0059 (14)0.077 (5)0.305 (16)
H57A0.4994−0.0483−0.03060.092*0.305 (16)
C58A0.5962 (16)−0.0181 (14)−0.0400 (12)0.084 (5)0.305 (16)
H58A0.6042−0.0373−0.08760.100*0.305 (16)
C59A0.6471 (13)0.0173 (14)−0.0031 (14)0.078 (4)0.305 (16)
H59A0.68910.0217−0.02600.094*0.305 (16)
C60A0.6351 (11)0.0461 (13)0.0680 (14)0.067 (4)0.305 (16)
C61A0.6951 (19)0.0703 (18)0.109 (2)0.069 (4)0.305 (16)
H61A0.72880.09230.08160.083*0.305 (16)
C62A0.7034 (19)0.060 (2)0.1941 (18)0.073 (4)0.305 (16)
H62A0.74890.06230.20620.087*0.305 (16)
C63A0.664 (2)0.048 (2)0.266 (2)0.069 (4)0.305 (16)
C64A0.6841 (15)0.020 (2)0.335 (2)0.074 (4)0.305 (16)
H64A0.72880.02380.35060.089*0.305 (16)
C65A0.6376 (16)−0.0119 (17)0.3818 (18)0.074 (5)0.305 (16)
H65A0.6511−0.03010.42830.088*0.305 (16)
C66A0.5707 (15)−0.0169 (17)0.359 (2)0.067 (5)0.305 (16)
H66A0.5396−0.03850.39000.080*0.305 (16)
C67A0.5505 (19)0.010 (2)0.289 (3)0.064 (4)0.305 (16)
H67A0.50580.00700.27410.077*0.305 (16)
C68A0.597 (3)0.043 (2)0.2429 (19)0.060 (4)0.305 (16)
C2S0.9015 (4)0.2278 (5)−0.7074 (4)0.141 (6)
H2S0.90000.2771−0.70690.169*
Cl60.8807 (9)0.1984 (9)−0.6167 (4)0.205 (8)0.60
Cl70.9823 (4)0.2023 (10)−0.7313 (11)0.182 (7)0.60
Cl80.8439 (6)0.1985 (9)−0.7743 (6)0.171 (6)0.60
Cl6A0.8781 (16)0.1686 (13)−0.6377 (10)0.213 (10)0.40
Cl7A0.9894 (4)0.2278 (15)−0.7147 (16)0.168 (9)0.40
Cl8A0.8676 (13)0.2024 (16)−0.7954 (8)0.195 (10)0.40
C3S0.9472 (8)0.1616 (12)−0.0093 (10)0.178 (16)*0.50
H3SA0.95450.20780.00850.214*0.50
Cl90.9319 (8)0.1577 (8)−0.1072 (9)0.203 (5)*0.50
Cl101.0123 (7)0.1075 (7)0.0173 (9)0.191 (5)*0.50
Cl110.8718 (8)0.1281 (8)0.0235 (9)0.202 (5)*0.50
C1S0.8771 (9)0.1196 (7)−0.3571 (9)0.174 (16)*0.50
H1S0.82960.1086−0.34860.209*0.50
Cl30.9285 (11)0.0522 (7)−0.3290 (10)0.263 (8)*0.50
Cl40.8997 (9)0.1906 (7)−0.3039 (8)0.226 (6)*0.50
Cl50.8915 (10)0.1362 (8)−0.4541 (7)0.255 (8)*0.50
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Pd10.0611 (4)0.0510 (3)0.0534 (3)−0.0077 (2)−0.0145 (3)0.0077 (3)
P20.0676 (12)0.0490 (10)0.0485 (10)−0.0017 (8)−0.0124 (9)0.0068 (8)
P10.0576 (11)0.0479 (10)0.0491 (10)−0.0041 (8)−0.0124 (8)0.0043 (8)
Cl20.0803 (14)0.0791 (14)0.0707 (14)−0.0126 (11)−0.0330 (11)0.0156 (11)
Cl10.0904 (16)0.0877 (16)0.0831 (16)−0.0376 (13)−0.0170 (13)0.0199 (13)
O10.067 (3)0.057 (3)0.052 (3)0.002 (2)−0.019 (3)0.002 (2)
O20.058 (3)0.048 (3)0.047 (3)0.002 (2)−0.007 (2)0.006 (2)
O40.080 (4)0.050 (3)0.048 (3)0.002 (2)−0.019 (3)0.003 (2)
N10.052 (3)0.046 (3)0.065 (4)−0.008 (2)−0.007 (3)0.001 (3)
O30.075 (4)0.056 (3)0.053 (3)0.007 (2)−0.004 (3)0.014 (2)
N20.075 (4)0.053 (4)0.053 (4)0.001 (3)−0.007 (3)0.009 (3)
C10.082 (6)0.059 (4)0.038 (4)−0.005 (4)−0.017 (4)0.003 (3)
C20.094 (6)0.077 (6)0.047 (5)−0.026 (5)−0.014 (4)0.006 (4)
C30.115 (8)0.070 (6)0.047 (5)−0.027 (5)−0.007 (5)−0.016 (4)
C40.105 (8)0.080 (6)0.039 (4)−0.017 (5)0.001 (5)−0.001 (4)
C50.128 (10)0.092 (7)0.061 (6)−0.018 (7)0.006 (6)−0.019 (6)
C60.171 (15)0.111 (10)0.071 (7)−0.005 (9)0.006 (9)−0.032 (7)
C70.131 (9)0.097 (8)0.074 (7)0.021 (7)0.027 (7)−0.020 (6)
C80.103 (8)0.081 (6)0.060 (5)0.008 (5)0.005 (5)−0.010 (5)
C90.079 (5)0.061 (5)0.051 (5)−0.003 (4)−0.004 (4)−0.007 (3)
C100.072 (5)0.059 (4)0.032 (3)−0.005 (4)−0.007 (3)0.002 (3)
C110.062 (4)0.050 (4)0.044 (4)−0.009 (3)−0.009 (3)0.001 (3)
C120.048 (4)0.050 (4)0.059 (5)0.004 (3)−0.012 (3)0.002 (3)
C130.067 (5)0.055 (4)0.053 (4)0.006 (3)−0.013 (4)−0.014 (4)
C140.064 (5)0.058 (4)0.083 (7)−0.003 (4)−0.016 (4)−0.017 (4)
C150.051 (4)0.057 (4)0.067 (5)−0.005 (3)−0.011 (4)−0.007 (4)
C160.060 (5)0.101 (8)0.102 (9)−0.018 (5)−0.016 (5)−0.015 (6)
C170.071 (6)0.117 (8)0.077 (7)−0.032 (6)−0.006 (5)0.014 (6)
C180.101 (7)0.111 (8)0.068 (6)−0.028 (6)0.007 (6)0.014 (6)
C190.079 (6)0.095 (7)0.056 (5)−0.018 (5)0.000 (4)0.006 (4)
C200.061 (5)0.056 (4)0.063 (5)−0.008 (3)0.000 (4)0.003 (4)
C210.057 (5)0.043 (4)0.085 (6)0.001 (3)0.000 (4)−0.006 (4)
C220.080 (6)0.065 (5)0.078 (6)0.004 (4)0.014 (5)0.011 (5)
C230.125 (7)0.093 (6)0.091 (6)0.008 (5)0.026 (5)0.012 (5)
C240.110 (6)0.092 (6)0.125 (7)−0.021 (5)0.038 (6)−0.010 (6)
C250.095 (6)0.097 (6)0.117 (7)−0.023 (5)0.016 (5)−0.020 (5)
C260.063 (5)0.054 (4)0.131 (9)−0.014 (4)0.020 (6)−0.022 (6)
C270.081 (7)0.077 (6)0.121 (10)0.008 (5)−0.048 (7)−0.042 (7)
C280.105 (8)0.071 (6)0.074 (6)−0.004 (5)−0.007 (6)−0.018 (5)
C290.094 (7)0.049 (4)0.070 (6)−0.001 (4)−0.017 (5)0.000 (4)
C300.165 (13)0.068 (6)0.054 (5)0.012 (7)0.011 (7)−0.003 (4)
C310.125 (11)0.091 (8)0.082 (8)0.011 (7)0.026 (8)0.016 (6)
C320.069 (6)0.101 (7)0.076 (7)0.010 (5)0.005 (5)0.019 (6)
C330.069 (5)0.082 (6)0.058 (5)0.009 (4)−0.006 (4)0.011 (4)
C340.060 (5)0.061 (5)0.053 (4)0.002 (3)0.000 (4)0.006 (4)
C350.098 (7)0.067 (5)0.050 (5)0.008 (5)0.004 (5)0.014 (4)
C360.089 (7)0.089 (7)0.081 (7)0.001 (5)−0.007 (6)0.014 (6)
C370.083 (7)0.107 (8)0.109 (9)0.011 (6)0.021 (7)−0.002 (8)
C380.161 (13)0.101 (9)0.067 (7)0.045 (9)0.031 (8)0.016 (6)
C390.146 (8)0.123 (7)0.127 (8)0.021 (6)0.010 (6)0.016 (6)
C400.150 (8)0.115 (7)0.114 (7)0.009 (6)0.025 (6)−0.004 (6)
C410.157 (8)0.106 (7)0.091 (6)0.000 (6)0.010 (6)−0.011 (5)
C420.149 (7)0.097 (6)0.079 (6)0.003 (6)0.006 (6)0.012 (5)
C430.136 (11)0.078 (7)0.060 (6)0.007 (6)−0.003 (6)0.014 (5)
C440.113 (8)0.052 (5)0.065 (6)0.001 (4)−0.001 (5)0.011 (4)
C450.133 (9)0.054 (5)0.064 (6)0.012 (5)−0.021 (6)0.010 (4)
C460.100 (7)0.057 (5)0.054 (5)0.005 (4)−0.015 (5)−0.008 (4)
C470.086 (7)0.077 (6)0.096 (8)0.005 (5)−0.034 (6)−0.010 (5)
C480.104 (9)0.119 (10)0.097 (9)−0.013 (7)−0.053 (8)0.000 (7)
C490.116 (6)0.101 (6)0.086 (6)−0.015 (5)−0.040 (6)0.017 (5)
C500.146 (8)0.143 (8)0.139 (8)−0.019 (7)−0.031 (7)−0.006 (7)
C510.166 (9)0.154 (8)0.126 (8)−0.013 (7)−0.013 (7)−0.002 (7)
C520.156 (8)0.137 (8)0.116 (8)−0.019 (6)−0.015 (7)0.008 (6)
C530.193 (14)0.110 (9)0.040 (5)−0.018 (9)−0.010 (7)0.017 (5)
C540.167 (12)0.061 (5)0.059 (6)−0.026 (6)−0.029 (7)0.005 (4)
C550.069 (5)0.045 (5)0.059 (5)0.015 (5)−0.006 (4)0.011 (4)
C560.077 (6)0.047 (5)0.072 (6)0.005 (5)−0.004 (5)0.003 (4)
C570.098 (7)0.060 (6)0.074 (6)0.026 (6)−0.005 (6)−0.008 (5)
C580.107 (8)0.083 (7)0.064 (6)0.024 (7)0.005 (5)−0.012 (5)
C590.091 (7)0.073 (7)0.066 (5)0.010 (6)0.012 (5)0.015 (5)
C600.075 (6)0.059 (5)0.064 (5)0.008 (5)−0.003 (4)0.006 (5)
C610.074 (6)0.056 (6)0.093 (5)−0.003 (5)−0.002 (6)−0.004 (6)
C620.081 (6)0.058 (7)0.092 (5)−0.011 (5)−0.021 (5)−0.006 (5)
C630.075 (5)0.048 (7)0.080 (6)0.006 (5)−0.020 (4)−0.001 (5)
C640.086 (7)0.067 (8)0.087 (7)0.014 (6)−0.033 (5)−0.001 (6)
C650.105 (8)0.072 (8)0.071 (7)0.039 (6)−0.020 (6)0.008 (6)
C660.096 (7)0.056 (8)0.069 (5)0.036 (6)−0.004 (6)0.017 (5)
C670.086 (6)0.040 (7)0.071 (6)0.021 (5)−0.006 (5)0.019 (5)
C680.075 (4)0.043 (8)0.065 (5)0.009 (5)−0.019 (4)0.013 (5)
C55A0.067 (5)0.059 (5)0.061 (5)0.005 (4)−0.003 (3)0.002 (4)
C56A0.074 (9)0.047 (9)0.056 (8)0.008 (8)−0.016 (7)0.017 (7)
C57A0.094 (9)0.060 (9)0.076 (9)0.011 (9)−0.016 (9)−0.007 (7)
C58A0.101 (10)0.078 (10)0.072 (9)0.023 (9)−0.007 (8)−0.004 (8)
C59A0.093 (8)0.068 (8)0.073 (7)0.012 (8)0.010 (6)0.003 (7)
C60A0.076 (7)0.055 (7)0.070 (7)0.002 (7)0.005 (5)0.008 (6)
C61A0.066 (7)0.056 (9)0.086 (6)0.010 (8)0.003 (7)0.008 (8)
C62A0.076 (7)0.052 (10)0.089 (7)0.001 (8)−0.012 (6)0.006 (8)
C63A0.079 (6)0.051 (9)0.078 (6)0.007 (7)−0.016 (5)0.002 (7)
C64A0.085 (8)0.061 (10)0.077 (8)0.022 (8)−0.018 (6)−0.003 (8)
C65A0.092 (10)0.057 (10)0.072 (8)0.037 (9)−0.017 (7)0.012 (8)
C66A0.085 (9)0.045 (11)0.070 (8)0.035 (9)−0.009 (8)0.012 (8)
C67A0.080 (7)0.046 (11)0.066 (8)0.020 (8)−0.008 (6)0.013 (8)
C68A0.077 (6)0.033 (9)0.069 (7)0.009 (8)−0.012 (5)0.001 (7)
C2S0.121 (11)0.148 (13)0.155 (15)−0.028 (10)−0.036 (10)0.019 (11)
Cl60.224 (11)0.248 (18)0.143 (8)−0.111 (13)−0.047 (8)0.046 (10)
Cl70.149 (8)0.182 (15)0.214 (17)0.004 (7)−0.039 (8)0.025 (12)
Cl80.209 (11)0.131 (8)0.173 (9)−0.040 (8)−0.092 (9)0.023 (8)
Cl6A0.26 (2)0.179 (19)0.203 (18)−0.047 (15)−0.004 (17)0.037 (15)
Cl7A0.153 (12)0.20 (2)0.155 (12)0.029 (11)−0.047 (9)−0.031 (13)
Cl8A0.27 (2)0.138 (12)0.171 (14)−0.101 (14)−0.104 (15)0.046 (11)
Geometric parameters (Å, °) top
Pd1—P22.232 (2)C40—C411.35 (2)
Pd1—P12.232 (2)C40—H400.9300
Pd1—Cl22.334 (2)C41—C421.36 (2)
Pd1—Cl12.343 (2)C41—H410.9300
P2—O41.615 (6)C42—C431.457 (19)
P2—O31.617 (6)C42—H420.9300
P2—N21.625 (7)C43—C441.426 (16)
P1—O21.601 (5)C44—C451.483 (16)
P1—O11.608 (6)C45—C461.385 (15)
P1—N11.630 (6)C45—C541.473 (15)
O1—C11.387 (11)C46—C471.397 (15)
O2—C121.397 (9)C47—C481.398 (16)
O4—C461.434 (10)C47—H470.9300
N1—C341.448 (11)C48—C491.42 (2)
N1—C211.463 (10)C48—H480.9300
O3—C351.396 (11)C49—C541.391 (19)
N2—C68A1.38 (3)C49—C501.45 (2)
N2—C55A1.441 (19)C50—C511.38 (3)
N2—C681.481 (13)C50—H500.9300
N2—C551.487 (10)C51—C521.31 (2)
C1—C101.361 (12)C51—H510.9300
C1—C21.432 (11)C52—C531.32 (2)
C2—C31.334 (14)C52—H520.9300
C2—H2A0.9300C53—C541.428 (19)
C3—C41.397 (15)C53—H530.9300
C3—H30.9300C55—C561.3900
C4—C51.379 (16)C55—C601.3900
C4—C91.450 (12)C56—C571.3900
C5—C61.35 (2)C56—H560.9300
C5—H50.9300C57—C581.3900
C6—C71.50 (2)C57—H570.9300
C6—H60.9300C58—C591.3900
C7—C81.335 (14)C58—H580.9300
C7—H70.9300C59—C601.3900
C8—C91.428 (15)C59—H590.9300
C8—H80.9300C60—C611.564 (18)
C9—C101.466 (12)C61—C621.24 (3)
C10—C111.467 (10)C61—H610.9300
C11—C121.411 (11)C62—C631.44 (2)
C11—C201.444 (11)C62—H620.9300
C12—C131.414 (10)C63—C641.3900
C13—C141.352 (13)C63—C681.3900
C13—H130.9300C64—C651.3900
C14—C151.428 (13)C64—H640.9300
C14—H140.9300C65—C661.3900
C15—C201.415 (11)C65—H650.9300
C15—C161.431 (13)C66—C671.3900
C16—C171.348 (16)C66—H660.9300
C16—H160.9300C67—C681.3900
C17—C181.380 (16)C67—H670.9300
C17—H170.9300C55A—C56A1.3900
C18—C191.350 (14)C55A—C60A1.3900
C18—H180.9300C56A—C57A1.3900
C19—C201.413 (13)C56A—H56A0.9300
C19—H190.9300C57A—C58A1.3900
C21—C221.361 (13)C57A—H57A0.9300
C21—C261.415 (14)C58A—C59A1.3900
C22—C231.424 (16)C58A—H58A0.9300
C22—H220.9300C59A—C60A1.3900
C23—C241.46 (2)C59A—H59A0.9300
C23—H230.9300C60A—C61A1.47 (4)
C24—C251.26 (2)C61A—C62A1.51 (5)
C24—H240.9300C61A—H61A0.9300
C25—C261.383 (16)C62A—C63A1.501 (5)
C25—H250.9300C62A—H62A0.9300
C26—C271.512 (19)C63A—C64A1.3900
C27—C281.298 (17)C63A—C68A1.3900
C27—H270.9300C64A—C65A1.3900
C28—C291.445 (16)C64A—H64A0.9300
C28—H280.9300C65A—C66A1.3900
C29—C341.408 (13)C65A—H65A0.9300
C29—C301.409 (16)C66A—C67A1.3900
C30—C311.375 (19)C66A—H66A0.9300
C30—H300.9300C67A—C68A1.3900
C31—C321.354 (18)C67A—H67A0.9300
C31—H310.9300C2S—Cl71.734 (8)
C32—C331.381 (14)C2S—Cl81.737 (8)
C32—H320.9300C2S—Cl61.740 (8)
C33—C341.365 (12)C2S—Cl7A1.751 (8)
C33—H330.9300C2S—Cl8A1.755 (8)
C35—C441.379 (14)C2S—Cl6A1.756 (8)
C35—C361.381 (15)C2S—H2S0.9800
C36—C371.355 (17)C3S—Cl111.736 (8)
C36—H360.9300C3S—Cl91.741 (8)
C37—C381.46 (2)C3S—Cl101.746 (8)
C37—H370.9300C3S—H3SA0.9800
C38—C431.37 (2)C1S—Cl41.748 (8)
C38—C391.44 (2)C1S—Cl51.751 (8)
C39—C401.35 (2)C1S—Cl31.755 (8)
C39—H390.9300C1S—H1S0.9800
P2—Pd1—P194.59 (7)C39—C40—H40120.1
P2—Pd1—Cl2174.48 (10)C40—C41—C42122.7 (16)
P1—Pd1—Cl288.86 (8)C40—C41—H41118.7
P2—Pd1—Cl187.73 (8)C42—C41—H41118.7
P1—Pd1—Cl1174.22 (10)C41—C42—C43120.3 (16)
Cl2—Pd1—Cl189.24 (9)C41—C42—H42119.8
O4—P2—O3101.0 (3)C43—C42—H42119.8
O4—P2—N2111.8 (3)C38—C43—C44119.0 (12)
O3—P2—N2100.0 (3)C38—C43—C42115.2 (13)
O4—P2—Pd1110.5 (2)C44—C43—C42125.7 (14)
O3—P2—Pd1116.4 (2)C35—C44—C43118.5 (11)
N2—P2—Pd1115.9 (3)C35—C44—C45120.2 (9)
O2—P1—O1102.0 (3)C43—C44—C45121.2 (10)
O2—P1—N1113.3 (3)C46—C45—C54114.9 (11)
O1—P1—N199.0 (3)C46—C45—C44121.5 (9)
O2—P1—Pd1108.2 (2)C54—C45—C44123.6 (11)
O1—P1—Pd1117.5 (2)C45—C46—C47126.1 (9)
N1—P1—Pd1116.1 (2)C45—C46—O4118.8 (9)
C1—O1—P1123.4 (5)C47—C46—O4115.0 (9)
C12—O2—P1122.8 (4)C48—C47—C46117.1 (12)
C46—O4—P2120.9 (5)C48—C47—H47121.4
C34—N1—C21115.7 (6)C46—C47—H47121.4
C34—N1—P1123.3 (5)C47—C48—C49120.1 (12)
C21—N1—P1120.9 (6)C47—C48—H48119.9
C35—O3—P2120.4 (5)C49—C48—H48119.9
C68A—N2—C55A126 (2)C54—C49—C48121.2 (11)
C55A—N2—C68119.5 (15)C54—C49—C50118.5 (15)
C68A—N2—C55115 (2)C48—C49—C50120.3 (14)
C68—N2—C55109.3 (10)C51—C50—C49112.2 (17)
C68A—N2—P2121 (2)C51—C50—H50123.9
C55A—N2—P2113.0 (11)C49—C50—H50123.9
C68—N2—P2126.5 (10)C52—C51—C50132 (2)
C55—N2—P2124.0 (6)C52—C51—H51114.1
C10—C1—O1120.3 (7)C50—C51—H51114.1
C10—C1—C2122.7 (8)C51—C52—C53115.5 (19)
O1—C1—C2116.8 (8)C51—C52—H52122.2
C3—C2—C1118.6 (10)C53—C52—H52122.2
C3—C2—H2A120.7C52—C53—C54121.7 (17)
C1—C2—H2A120.7C52—C53—H53119.2
C2—C3—C4123.2 (9)C54—C53—H53119.2
C2—C3—H3118.4C49—C54—C53120.4 (11)
C4—C3—H3118.4C49—C54—C45119.7 (12)
C5—C4—C3120.5 (10)C53—C54—C45119.8 (13)
C5—C4—C9120.3 (11)C56—C55—C60120.0
C3—C4—C9118.9 (8)C56—C55—N2116.6 (6)
C6—C5—C4119.8 (11)C60—C55—N2123.2 (6)
C6—C5—H5120.1C55—C56—C57120.0
C4—C5—H5120.1C55—C56—H56120.0
C5—C6—C7121.6 (12)C57—C56—H56120.0
C5—C6—H6119.2C58—C57—C56120.0
C7—C6—H6119.2C58—C57—H57120.0
C8—C7—C6117.8 (13)C56—C57—H57120.0
C8—C7—H7121.1C57—C58—C59120.0
C6—C7—H7121.1C57—C58—H58120.0
C7—C8—C9121.5 (11)C59—C58—H58120.0
C7—C8—H8119.3C58—C59—C60120.0
C9—C8—H8119.3C58—C59—H59120.0
C8—C9—C4118.8 (8)C60—C59—H59120.0
C8—C9—C10123.6 (8)C59—C60—C55120.0
C4—C9—C10117.6 (8)C59—C60—C61122.1 (8)
C1—C10—C9118.1 (7)C55—C60—C61117.8 (8)
C1—C10—C11122.1 (7)C62—C61—C60130.9 (15)
C9—C10—C11119.6 (7)C62—C61—H61114.6
C12—C11—C20116.5 (7)C60—C61—H61114.6
C12—C11—C10120.0 (7)C61—C62—C63123.6 (16)
C20—C11—C10123.5 (7)C61—C62—H62118.2
O2—C12—C11120.6 (6)C63—C62—H62118.2
O2—C12—C13117.5 (7)C64—C63—C68120.0
C11—C12—C13121.8 (7)C64—C63—C62113.0 (14)
C14—C13—C12119.3 (8)C68—C63—C62126.9 (14)
C14—C13—H13120.4C63—C64—C65120.0
C12—C13—H13120.4C63—C64—H64120.0
C13—C14—C15122.8 (8)C65—C64—H64120.0
C13—C14—H14118.6C64—C65—C66120.0
C15—C14—H14118.6C64—C65—H65120.0
C20—C15—C14117.3 (7)C66—C65—H65120.0
C20—C15—C16119.9 (9)C65—C66—C67120.0
C14—C15—C16122.6 (8)C65—C66—H66120.0
C17—C16—C15121.2 (9)C67—C66—H66120.0
C17—C16—H16119.4C68—C67—C66120.0
C15—C16—H16119.4C68—C67—H67120.0
C16—C17—C18118.2 (9)C66—C67—H67120.0
C16—C17—H17120.9C67—C68—C63120.0
C18—C17—H17120.9C67—C68—N2120.5 (12)
C19—C18—C17123.0 (11)C63—C68—N2119.4 (12)
C19—C18—H18118.5C56A—C55A—C60A120.0
C17—C18—H18118.5C56A—C55A—N2126.3 (14)
C18—C19—C20121.3 (10)C60A—C55A—N2113.6 (14)
C18—C19—H19119.3C57A—C56A—C55A120.0
C20—C19—H19119.3C57A—C56A—H56A120.0
C19—C20—C15116.2 (8)C55A—C56A—H56A120.0
C19—C20—C11122.4 (8)C56A—C57A—C58A120.0
C15—C20—C11121.4 (8)C56A—C57A—H57A120.0
C22—C21—C26121.6 (9)C58A—C57A—H57A120.0
C22—C21—N1120.5 (8)C59A—C58A—C57A120.0
C26—C21—N1117.8 (9)C59A—C58A—H58A120.0
C21—C22—C23118.8 (11)C57A—C58A—H58A120.0
C21—C22—H22120.6C60A—C59A—C58A120.0
C23—C22—H22120.6C60A—C59A—H59A120.0
C22—C23—C24116.0 (12)C58A—C59A—H59A120.0
C22—C23—H23122.0C59A—C60A—C55A120.0
C24—C23—H23122.0C59A—C60A—C61A115 (2)
C25—C24—C23121.4 (12)C55A—C60A—C61A123 (2)
C25—C24—H24119.3C60A—C61A—C62A121 (3)
C23—C24—H24119.3C60A—C61A—H61A119.3
C24—C25—C26123.8 (14)C62A—C61A—H61A119.3
C24—C25—H25118.1C63A—C62A—H62A109.0
C26—C25—H25118.1C61A—C62A—H62A109.0
C25—C26—C21116.5 (13)C64A—C63A—C68A120.0
C25—C26—C27121.4 (11)C64A—C63A—C62A130 (3)
C21—C26—C27122.1 (9)C68A—C63A—C62A106 (3)
C28—C27—C26127.1 (10)C65A—C64A—C63A120.0
C28—C27—H27116.4C65A—C64A—H64A120.0
C26—C27—H27116.5C63A—C64A—H64A120.0
C27—C28—C29126.9 (11)C64A—C65A—C66A120.0
C27—C28—H28116.5C64A—C65A—H65A120.0
C29—C28—H28116.5C66A—C65A—H65A120.0
C34—C29—C30117.8 (10)C67A—C66A—C65A120.0
C34—C29—C28123.7 (9)C67A—C66A—H66A120.0
C30—C29—C28118.4 (10)C65A—C66A—H66A120.0
C31—C30—C29120.2 (11)C68A—C67A—C66A120.0
C31—C30—H30119.9C68A—C67A—H67A120.0
C29—C30—H30119.9C66A—C67A—H67A120.0
C32—C31—C30121.3 (12)N2—C68A—C67A113 (3)
C32—C31—H31119.3N2—C68A—C63A127 (3)
C30—C31—H31119.3C67A—C68A—C63A120.0
C31—C32—C33119.3 (11)Cl7—C2S—Cl8110.4 (6)
C31—C32—H32120.4Cl7—C2S—Cl6110.0 (6)
C33—C32—H32120.4Cl8—C2S—Cl6110.3 (5)
C34—C33—C32121.5 (9)Cl6—C2S—Cl7A107.7 (16)
C34—C33—H33119.2Cl7A—C2S—Cl8A108.6 (6)
C32—C33—H33119.2Cl7—C2S—Cl6A102.5 (18)
C33—C34—C29119.8 (9)Cl7A—C2S—Cl6A108.4 (6)
C33—C34—N1121.0 (8)Cl8A—C2S—Cl6A108.4 (6)
C29—C34—N1119.1 (7)Cl7—C2S—H2S108.7
C44—C35—C36123.3 (10)Cl8—C2S—H2S108.7
C44—C35—O3117.6 (9)Cl6—C2S—H2S108.7
C36—C35—O3118.9 (9)Cl7A—C2S—H2S91.7
C37—C36—C35118.5 (11)Cl8A—C2S—H2S106.4
C37—C36—H36120.7Cl6A—C2S—H2S131.0
C35—C36—H36120.7Cl11—C3S—Cl999.1 (12)
C36—C37—C38120.3 (12)Cl11—C3S—Cl10108.3 (13)
C36—C37—H37119.9Cl9—C3S—Cl10111.3 (14)
C38—C37—H37119.9Cl11—C3S—H3SA112.4
C43—C38—C39122.3 (16)Cl9—C3S—H3SA112.4
C43—C38—C37119.9 (11)Cl10—C3S—H3SA112.4
C39—C38—C37117.8 (16)Cl4—C1S—Cl5108.8 (6)
C40—C39—C38119.5 (18)Cl4—C1S—Cl3108.5 (6)
C40—C39—H39120.3Cl5—C1S—Cl3108.7 (6)
C38—C39—H39120.3Cl4—C1S—H1S110.3
C41—C40—C39119.9 (17)Cl5—C1S—H1S110.3
C41—C40—H40120.1Cl3—C1S—H1S110.3
Hydrogen-bond geometry (Å, °) top
D—H···AD—HH···AD···AD—H···A
C2S—H2S···Cl1i0.972.473.358 (10)151
C27—H27···Cl2ii0.932.823.741 (12)172
C14—H14···Cl2ii0.932.843.613 (10)142
Symmetry codes: (i) −y+1, x, z−3/4; (ii) −y+1, x, z+1/4.
Table 1
Selected geometric parameters (Å) top
Pd1—P22.232 (2)Pd1—Cl22.334 (2)
Pd1—P12.232 (2)Pd1—Cl12.343 (2)
Table 2
Hydrogen-bond geometry (Å, °) top
D—H···AD—HH···AD···AD—H···A
C2S—H2S···Cl1i0.972.473.358 (10)151
C27—H27···Cl2ii0.932.823.741 (12)172
C14—H14···Cl2ii0.932.843.613 (10)142
Symmetry codes: (i) −y+1, x, z−3/4; (ii) −y+1, x, z+1/4.
Acknowledgements top

This work was possible thanks to FONACIT-MCT (projects S1–2001000851 and LAB-199700821).

references
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