metal-organic compounds\(\def\hfill{\hskip 5em}\def\hfil{\hskip 3em}\def\eqno#1{\hfil {#1}}\)

Journal logoCRYSTALLOGRAPHIC
COMMUNICATIONS
ISSN: 2056-9890
Volume 67| Part 4| April 2011| Pages m416-m417

[1,2-Bis(di­phenyl­phosphan­yl)ethane-κ2P,P′]{2-[(4-nitro­benzoyl­meth­yl)di­phenyl­phosphan­yl]phenyl-κ2C,C′}palladium(II) tri­fluoro­methane­sulfonate–di­chloro­methane–n-hexane (1/1/0.5)

aDipartimento di Chimica Generale ed Inorganica, Chimica Analitica, Chimica Fisica, Universitá degli Studi di Parma, Viale G. P. Usberti 17/A, I-43124 Parma, Italy, and bDepartment of Chemistry, Isfahan University of Technology, Isfahan 84156/83111, Iran
*Correspondence e-mail: corrado.rizzoli@unipr.it

(Received 25 February 2011; accepted 3 March 2011; online 9 March 2011)

In the cation of the title compound, [Pd(C26H19NO3P)(C26H24P2)]CF3O3S·CH2Cl2·0.5C6H14, the PdII atom has a slightly tetra­hedrally distorted square-planar coordination geometry. The PdC3P and PdC2P2 five-membered metallacycles adopt envelope and twist conformations, respectively. In the crystal, inter­molecular C—H⋯O hydrogen bonds link cations and anions into a three-dimensional network. The dichloro­methane solvent mol­ecule is disordered over three orientations with a site-occupancy ratio of 0.5/0.3/0.2. The n-hexane solvent mol­ecule has a crystallographically imposed centre of symmetry.

Related literature

For the synthesis and applications as catalysts of cyclo­palladated metal complexes, see: Rietling et al. (2002[Rietling, V., Sirlin, C. & Pfeffer, M. (2002). Chem. Rev. 102, 1731-1770.]); Aguilar et al. (2008[Aguilar, D., Aragues, M. A., Bielsa, R., Serrano, E., Soler, T., Navarro, R. & Urriolabeitia, E. P. (2008). J. Organomet. Chem. 693, 417-424.]); Dupont et al. (2001[Dupont, J., Pfeffer, M. & Spencer, J. (2001). Eur. J. Inorg. Chem. pp. 1917-1927.]); Chen et al. (2009[Chen, X., Engle, K. M., Wang, D.-H. & Yu, J.-Q. (2009). Angew. Chem. Int. Ed. 48, 5094-5115.]). For ortho-palladated α-ketophospho­rus ylides complexes reported by our group, see: Karami et al. (2010[Karami, K., Büyükgüngör, O. & Dalvand, H. (2010). Transition Met. Chem. 35, 621-626.]); Karami, Rizzoli & Salah (2011[Karami, K., Rizzoli, C. & Salah, M. M. (2011). J. Organomet. Chem. 696, 940-945.]); Karami, Rizzoli & Borzooie (2011[Karami, K., Rizzoli, C. & Borzooie, F. (2011). Polyhedron, 30, 778-784.]). For related structures, see: Falvello et al. (1998[Falvello, L. R., Fernandez, S., Navarro, R., Rueda, A. & Urriolabeitia, E. P. (1998). Organometallics, 17, 5887-5900.], 1999[Falvello, L. R., Fernandez, S., Navarro, R. & Urriolabeitia, E. P. (1999). Inorg. Chem. 38, 2455-2463.]); Shao et al. (1982[Shao, M., Jin, X., Tang, Y., Huang, Q. & Huang, Y. (1982). Tetrahedron Lett. 23, 5343-5346.]).

[Scheme 1]

Experimental

Crystal data
  • [Pd(C26H19NO3P)(C26H24P2)]CF3O3S·CH2Cl2·0.5C6H14

  • Mr = 1206.27

  • Monoclinic, P 21 /n

  • a = 12.4063 (7) Å

  • b = 14.2445 (8) Å

  • c = 31.3633 (17) Å

  • β = 91.6675 (9)°

  • V = 5540.2 (5) Å3

  • Z = 4

  • Mo Kα radiation

  • μ = 0.62 mm−1

  • T = 294 K

  • 0.19 × 0.16 × 0.10 mm

Data collection
  • Bruker APEXII CCD diffractometer

  • Absorption correction: multi-scan (SADABS; Bruker, 2008[Bruker (2008). APEX2, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.]) Tmin = 0.872, Tmax = 0.955

  • 62924 measured reflections

  • 10529 independent reflections

  • 8106 reflections with I > 2σ(I)

  • Rint = 0.036

Refinement
  • R[F2 > 2σ(F2)] = 0.029

  • wR(F2) = 0.076

  • S = 1.04

  • 10529 reflections

  • 691 parameters

  • 14 restraints

  • H-atom parameters constrained

  • Δρmax = 0.37 e Å−3

  • Δρmin = −0.38 e Å−3

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A D—H H⋯A DA D—H⋯A
C19—H19⋯O1i 0.93 2.54 3.284 (3) 138
C30—H30⋯O6ii 0.93 2.55 3.372 (4) 148
C39—H39B⋯O6iii 0.97 2.59 3.309 (4) 131
Symmetry codes: (i) -x+1, -y, -z; (ii) x, y-1, z; (iii) [-x+{\script{3\over 2}}, y-{\script{1\over 2}}, -z+{\script{1\over 2}}].

Data collection: APEX2 (Bruker, 2008[Bruker (2008). APEX2, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.]); cell refinement: APEX2; data reduction: SAINT (Bruker, 2008[Bruker (2008). APEX2, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.]); program(s) used to solve structure: SIR97 (Altomare et al., 1999[Altomare, A., Burla, M. C., Camalli, M., Cascarano, G. L., Giacovazzo, C., Guagliardi, A., Moliterni, A. G. G., Polidori, G. & Spagna, R. (1999). J. Appl. Cryst. 32, 115-119.]); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997[Farrugia, L. J. (1997). J. Appl. Cryst. 30, 565.]) and SCHAKAL97 (Keller, 1997[Keller, E. (1997). SCHAKAL97. University of Freiburg, Germany.]); software used to prepare material for publication: SHELXL97 and PARST95 (Nardelli, 1995[Nardelli, M. (1995). J. Appl. Cryst. 28, 659.]).

Supporting information


Comment top

The synthesis and characterization of cyclopalladated metal complexes (Rietling et al., 2002) has attracted considerable attention due to their potential applications in organic synthesis and homogenous catalysis (Aguilar et al., 2008; Dupont et al., 2001; Chen et al., 2009). As a continuation of our ongoing project devoted to the development of new catalysts based on ortho-palladated α-ketophosphorus ylides complexes (Karami et al., 2010; Karami, Rizzoli & Salah, 2011; Karami, Rizzoli & Borzooie, 2011), we report herein the synthesis and crystal structure of the title compound.

The asymmetric unit of the title compound (Fig. 1) consists of one mononuclear complex cation, one trifluoromethanesulfonate anion, one disordered dichloromethane molecule and half an n-hexane lying on a centre of symmetry. In the cation (Fig. 2), the palladium(II) atom displays a slightly but not negligibly tetrahedrally distorted square planar coordination geometry, with atoms P2, P3, C1 and C9 displaced from the mean plane through the P2C2 core by -0.0061 (6), 0.0055 (6), -0.070 (2) and 0.069 (2) Å, respectively. The distortion from the regular square planar geometry is also indicated by the values of the cis and trans angles subtended at the metal, which range from 83.17 (8) to 100.49 (5)°, and from 175.31 (5) to 175.68 (5)°, respectively. The Pd–C bond lengths involving the aromatic and ylidic carbon atoms (Pd1–C9 = 2.0783 (19) Å; Pd–C1 = 2.1711 (19) Å) are in agreement with those observed in related cyclopalladated complexes (Falvello et al., 1998; Falvello et al., 1999; Karami et al., 2010; Karami, Rizzoli & Salah, 2011; Karami, Rizzoli & Borzooie, 2011). The P1–C1 bond length (1.768 (2) Å) is significantly longer than that observed in the related free ylide (1.711 Å) of formula PPh3C(H)COPh (Shao et al., 1982). The Pd1···P1 separation is 3.0241 (9) Å. The PdC3P five-membered metallacycle (Pd1/C9/C14/P1/C1) assumes an envelope conformation, with atom C1 displaced by 1.006 (2) Å from the mean planes of the remaining four atoms, whereas the PdC2P2 metallacycle (Pd1/P2/C39/C40/P3) adopts a twist conformation with the local twofold axis passing through the C39–C40 bond and the Pd atom. In the crystal structure (Fig. 3), cations and anions are linked into a three-dimensional network by intermolecular C—H···O hydrogen bonds (Table 1).

Related literature top

For the synthesis and applications as catalysts of cyclopalladated metal complexes, see: Rietling et al. (2002); Aguilar et al. (2008); Dupont et al. (2001); Chen et al. (2009). For ortho-palladated α-ketophosphorus ylides complexes reported by our group, see: Karami et al. (2010); Karami, Rizzoli & Salah (2011); Karami, Rizzoli & Borzooie (2011). For related structures, see: Falvello et al. (1998, 1999); Shao et al. (1982).

Experimental top

The title compound was obtained according to the procedure recently reported elsewhere (Karami, Rizzoli & Borzooie, 2011). Crystals suitable for X-ray analysis were obtained by slow evaporation of a dichloromethane/n-hexane (1:1 v/v) solution at room temperature.

Refinement top

All H atoms were placed in calculated positions and refined using a riding model, with C–H = 0.93–0.98 Å, and with Uiso(H) = 1.2 Ueq(C) or 1.5 Ueq(C) for methyl H atoms. The dichloromethane solvent molecule was found to be disordered over three orientations (called A, B, and C) with site-occupancy factors of 1/2, 0.3 and 1/5, respectively. During the refinement, the C–Cl and Cl···Cl distances were constrained to 1.75 (1) and 2.75 (2) Å, respectively, and only the major component of disorder was refined anisotropically. The n-hexane molecule, which has crystallographically imposed centre of symmetry, showed rather high displacement ellipsoids, suggesting the presence of disorder. Attempts to model the molecule in terms of disordered contributors were unsuccessful, however. The molecule was therefore anisotropically refined by constraining the C–C bond lengths to 1.54 (1) Å, and the 1–3 C···C separations to 2.52 (2) Å.

Computing details top

Data collection: APEX2 (Bruker, 2008); cell refinement: APEX2 (Bruker, 2008); data reduction: SAINT (Bruker, 2008); program(s) used to solve structure: SIR97 (Altomare et al., 1999); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997) and SCHAKAL97 (Keller, 1997); software used to prepare material for publication: SHELXL97 (Sheldrick, 2008) and PARST95 (Nardelli, 1995).

Figures top
[Figure 1] Fig. 1. The asymmetric unit of the title compound, with displacement ellipsoids drawn at the 30% probability level. Only the major component of the disordered dichloromethane molecule is shown. Symmetry code: (i) -x, 1 - y, -z.
[Figure 2] Fig. 2. The cation of the title compound, showing the labelling scheme adopted. Displacement ellipsoids are drawn at the 30% probability level. Hydrogen atoms are omitted for clarity.
[Figure 3] Fig. 3. Crystal packing of the title compound approximately viewed along the a axis. Only the major component of the disordered dichloromethane molecule is shown. Hydrogen atoms not involved in intermolecular C—H···O hydrogen bonds (dashed lines) are omitted for clarity.
[1,2-Bis(diphenylphosphanyl)ethane-κ2P,P']{2-[(4- nitrobenzoylmethyl)diphenylphosphanyl]phenyl- κ2C,C'}palladium(II) trifluoromethanesulfonate–dichloromethane–n-hexane (1/1/0.5) top
Crystal data top
[Pd(C26H19NO3P)(C26H24P2)]CF3O3S·CH2Cl2·0.5C6H14F(000) = 2468
Mr = 1206.27Dx = 1.446 Mg m3
Monoclinic, P21/nMo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ynCell parameters from 1226 reflections
a = 12.4063 (7) Åθ = 6.3–23.4°
b = 14.2445 (8) ŵ = 0.62 mm1
c = 31.3633 (17) ÅT = 294 K
β = 91.6675 (9)°Irregular block, yellow
V = 5540.2 (5) Å30.19 × 0.16 × 0.10 mm
Z = 4
Data collection top
Bruker APEXII CCD
diffractometer
10529 independent reflections
Radiation source: fine-focus sealed tube8106 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.036
ω scansθmax = 25.7°, θmin = 1.6°
Absorption correction: multi-scan
(SADABS; Bruker, 2008)
h = 1515
Tmin = 0.872, Tmax = 0.955k = 1717
62924 measured reflectionsl = 3838
Refinement top
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.029Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.076H-atom parameters constrained
S = 1.04 w = 1/[σ2(Fo2) + (0.038P)2]
where P = (Fo2 + 2Fc2)/3
10529 reflections(Δ/σ)max = 0.001
691 parametersΔρmax = 0.37 e Å3
14 restraintsΔρmin = 0.38 e Å3
Crystal data top
[Pd(C26H19NO3P)(C26H24P2)]CF3O3S·CH2Cl2·0.5C6H14V = 5540.2 (5) Å3
Mr = 1206.27Z = 4
Monoclinic, P21/nMo Kα radiation
a = 12.4063 (7) ŵ = 0.62 mm1
b = 14.2445 (8) ÅT = 294 K
c = 31.3633 (17) Å0.19 × 0.16 × 0.10 mm
β = 91.6675 (9)°
Data collection top
Bruker APEXII CCD
diffractometer
10529 independent reflections
Absorption correction: multi-scan
(SADABS; Bruker, 2008)
8106 reflections with I > 2σ(I)
Tmin = 0.872, Tmax = 0.955Rint = 0.036
62924 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.02914 restraints
wR(F2) = 0.076H-atom parameters constrained
S = 1.04Δρmax = 0.37 e Å3
10529 reflectionsΔρmin = 0.38 e Å3
691 parameters
Special details top

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)
Pd10.756229 (11)0.147230 (10)0.131977 (5)0.03814 (6)
S10.90642 (7)0.50943 (6)0.15555 (3)0.0883 (2)
P10.81951 (4)0.14269 (4)0.039724 (17)0.04289 (13)
P30.57524 (4)0.14972 (4)0.152637 (18)0.04526 (13)
P20.78566 (4)0.07474 (4)0.196011 (17)0.04514 (14)
O10.57447 (13)0.19304 (12)0.03587 (6)0.0709 (5)
O20.5578 (3)0.68752 (18)0.07768 (10)0.1340 (10)
O30.4015 (3)0.6445 (2)0.06026 (13)0.1685 (14)
O40.8765 (2)0.57210 (17)0.12237 (9)0.1226 (8)
O50.82523 (18)0.44856 (18)0.17003 (8)0.1183 (8)
O60.9700 (3)0.5548 (2)0.18984 (9)0.1499 (11)
F10.9555 (2)0.3873 (2)0.09940 (9)0.1675 (11)
F21.0418 (2)0.37281 (17)0.16085 (10)0.1651 (11)
F31.08767 (16)0.47955 (15)0.11854 (7)0.1293 (7)
N10.4919 (3)0.6307 (2)0.06826 (9)0.0947 (9)
C10.74213 (16)0.21915 (14)0.07104 (6)0.0428 (5)
H10.78440.27700.07420.051*
C20.63523 (17)0.24779 (16)0.05422 (7)0.0487 (5)
C30.60121 (18)0.34836 (15)0.05941 (7)0.0524 (5)
C40.6672 (2)0.41801 (17)0.07639 (9)0.0697 (7)
H40.73630.40300.08650.084*
C50.6311 (3)0.51037 (18)0.07854 (10)0.0794 (8)
H50.67620.55740.08930.095*
C60.5308 (3)0.53044 (19)0.06495 (9)0.0731 (7)
C70.4620 (2)0.4644 (2)0.04858 (9)0.0828 (9)
H70.39230.48070.03970.099*
C80.4971 (2)0.37316 (19)0.04537 (8)0.0694 (7)
H80.45130.32760.03380.083*
C90.91717 (15)0.13543 (13)0.11614 (6)0.0398 (5)
C101.00786 (17)0.12915 (15)0.14348 (7)0.0502 (5)
H100.99880.12950.17280.060*
C111.11043 (17)0.12245 (18)0.12802 (8)0.0608 (6)
H111.16890.11860.14720.073*
C121.12825 (18)0.12141 (18)0.08535 (8)0.0641 (7)
H121.19810.11670.07550.077*
C131.04155 (18)0.12737 (16)0.05688 (7)0.0545 (6)
H131.05210.12680.02760.065*
C140.93907 (16)0.13423 (14)0.07244 (6)0.0424 (5)
C150.76628 (17)0.02642 (16)0.03113 (6)0.0490 (5)
C160.8100 (2)0.04862 (17)0.05335 (8)0.0621 (6)
H160.86590.03950.07330.074*
C170.7694 (3)0.13839 (18)0.04549 (10)0.0845 (9)
H170.79800.18940.06040.101*
C180.6875 (3)0.1518 (2)0.01586 (11)0.0873 (10)
H180.66100.21200.01080.105*
C190.6445 (2)0.0779 (2)0.00625 (9)0.0789 (8)
H190.58930.08770.02640.095*
C200.68299 (19)0.01173 (19)0.00130 (7)0.0618 (6)
H200.65310.06230.01360.074*
C210.84920 (18)0.18697 (18)0.01227 (7)0.0545 (6)
C220.8883 (2)0.1285 (2)0.04356 (8)0.0712 (7)
H220.89420.06430.03840.085*
C230.9187 (2)0.1647 (3)0.08236 (9)0.0815 (9)
H230.94860.12520.10250.098*
C240.9057 (3)0.2541 (3)0.09099 (11)0.1113 (12)
H240.92860.27810.11680.134*
C250.8589 (3)0.3115 (3)0.06240 (12)0.1215 (13)
H250.84280.37320.06990.146*
C260.8347 (3)0.2789 (2)0.02164 (10)0.1082 (12)
H260.80900.31990.00130.130*
C270.85865 (19)0.03586 (15)0.19613 (7)0.0533 (6)
C280.8165 (2)0.10762 (19)0.17098 (9)0.0715 (7)
H280.75430.09740.15440.086*
C290.8663 (3)0.1941 (2)0.17036 (11)0.0857 (9)
H290.83700.24220.15370.103*
C300.9574 (3)0.2089 (2)0.19399 (11)0.0962 (11)
H300.99030.26750.19370.115*
C311.0012 (3)0.1393 (3)0.21797 (11)0.1123 (13)
H311.06490.15010.23360.135*
C320.9523 (2)0.0517 (2)0.21953 (9)0.0830 (8)
H320.98270.00420.23630.100*
C330.84562 (17)0.15069 (15)0.23661 (7)0.0498 (5)
C340.8534 (2)0.1220 (2)0.27935 (8)0.0698 (7)
H340.83030.06250.28710.084*
C350.8953 (2)0.1821 (3)0.30950 (9)0.0839 (9)
H350.89990.16340.33790.101*
C360.9302 (2)0.2687 (3)0.29844 (10)0.0884 (9)
H360.96010.30820.31920.106*
C370.9221 (2)0.2985 (2)0.25752 (10)0.0777 (8)
H370.94570.35830.25040.093*
C380.87898 (18)0.24007 (17)0.22645 (8)0.0581 (6)
H380.87230.26110.19840.070*
C390.65511 (18)0.04531 (17)0.21851 (7)0.0572 (6)
H39A0.62570.01080.20500.069*
H39B0.66350.03380.24890.069*
C400.58024 (18)0.12801 (17)0.21030 (7)0.0556 (6)
H40A0.60710.18310.22540.067*
H40B0.50870.11380.22020.067*
C410.48826 (17)0.25194 (16)0.14711 (7)0.0513 (5)
C420.5253 (2)0.33604 (18)0.16386 (9)0.0713 (7)
H420.59420.33980.17620.086*
C430.4591 (3)0.4154 (2)0.16227 (9)0.0848 (9)
H430.48400.47200.17360.102*
C440.3585 (3)0.4099 (2)0.14422 (11)0.0940 (10)
H440.31410.46250.14390.113*
C450.3215 (2)0.3273 (2)0.12634 (12)0.0943 (10)
H450.25330.32430.11330.113*
C460.38683 (19)0.24915 (19)0.12800 (9)0.0733 (7)
H460.36200.19320.11600.088*
C470.49623 (16)0.04970 (15)0.13374 (7)0.0484 (5)
C480.40033 (18)0.02404 (18)0.15241 (9)0.0669 (7)
H480.37320.06100.17410.080*
C490.3453 (2)0.05461 (19)0.13946 (9)0.0732 (7)
H490.27990.06930.15160.088*
C500.3860 (2)0.11248 (18)0.10840 (9)0.0661 (7)
H500.34970.16690.10010.079*
C510.4797 (2)0.08836 (18)0.09037 (8)0.0662 (7)
H510.50770.12690.06940.079*
C520.53468 (18)0.00806 (16)0.10225 (7)0.0554 (6)
H520.59830.00740.08890.067*
C531.0025 (3)0.4339 (3)0.13228 (13)0.1008 (10)
C54A0.3163 (9)0.6781 (8)0.2291 (3)0.194 (5)0.50
H54A0.27410.72640.24270.232*0.50
H54B0.39220.69270.23340.232*0.50
Cl1A0.2831 (3)0.6713 (2)0.17539 (14)0.1998 (15)0.50
Cl2A0.2875 (4)0.5690 (5)0.25025 (15)0.288 (3)0.50
C54B0.2090 (16)0.6089 (8)0.2196 (4)0.141 (6)*0.30
H54C0.26230.61380.19770.170*0.30
H54D0.13820.62020.20670.170*0.30
Cl1B0.2144 (9)0.4956 (6)0.2440 (3)0.295 (5)*0.30
Cl2B0.2361 (6)0.6898 (5)0.2604 (2)0.198 (2)*0.30
C54C0.2675 (17)0.7357 (9)0.2117 (4)0.107 (6)*0.20
H54E0.33400.76190.20130.129*0.20
H54F0.20600.76570.19760.129*0.20
Cl1C0.2632 (13)0.6113 (9)0.2074 (5)0.245 (6)*0.20
Cl2C0.2614 (9)0.7397 (8)0.2671 (3)0.207 (4)*0.20
C550.1874 (6)0.3580 (5)0.0169 (3)0.281 (5)
H55A0.26280.35940.02480.421*
H55B0.17530.31340.00570.421*
H55C0.14670.34000.04120.421*
C560.1529 (5)0.4517 (5)0.0023 (2)0.220 (3)
H56A0.18770.46640.02410.265*
H56B0.17580.49800.02340.265*
C570.0311 (5)0.4582 (4)0.0047 (3)0.221 (4)
H57A0.01650.44370.03450.265*
H57B0.00030.40740.01160.265*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Pd10.03380 (9)0.04284 (10)0.03775 (9)0.00153 (7)0.00029 (6)0.00164 (7)
S10.0898 (6)0.0880 (5)0.0879 (6)0.0087 (5)0.0177 (5)0.0037 (5)
P10.0401 (3)0.0506 (3)0.0378 (3)0.0059 (2)0.0005 (2)0.0001 (2)
P30.0354 (3)0.0529 (3)0.0476 (3)0.0014 (2)0.0040 (2)0.0047 (3)
P20.0459 (3)0.0482 (3)0.0414 (3)0.0009 (2)0.0010 (2)0.0032 (2)
O10.0542 (10)0.0624 (10)0.0944 (13)0.0030 (8)0.0271 (9)0.0110 (10)
O20.193 (3)0.0650 (16)0.145 (2)0.0284 (18)0.019 (2)0.0046 (16)
O30.173 (3)0.112 (2)0.220 (4)0.076 (2)0.017 (3)0.022 (2)
O40.1203 (19)0.1035 (18)0.144 (2)0.0192 (15)0.0099 (16)0.0336 (16)
O50.0866 (15)0.135 (2)0.135 (2)0.0087 (15)0.0315 (14)0.0224 (16)
O60.186 (3)0.153 (2)0.111 (2)0.027 (2)0.0091 (19)0.0592 (18)
F10.154 (2)0.170 (2)0.178 (3)0.0203 (18)0.0109 (19)0.098 (2)
F20.143 (2)0.1191 (17)0.236 (3)0.0479 (15)0.049 (2)0.0631 (19)
F30.0921 (13)0.1338 (17)0.165 (2)0.0059 (12)0.0491 (13)0.0272 (15)
N10.120 (3)0.079 (2)0.0850 (19)0.0314 (19)0.0008 (18)0.0077 (16)
C10.0426 (11)0.0408 (11)0.0448 (12)0.0048 (9)0.0013 (9)0.0020 (9)
C20.0447 (12)0.0530 (13)0.0482 (12)0.0034 (10)0.0035 (10)0.0043 (10)
C30.0539 (13)0.0559 (14)0.0472 (13)0.0003 (11)0.0010 (10)0.0044 (11)
C40.0569 (15)0.0557 (16)0.096 (2)0.0003 (12)0.0026 (14)0.0078 (14)
C50.089 (2)0.0500 (16)0.099 (2)0.0038 (15)0.0033 (17)0.0065 (14)
C60.099 (2)0.0605 (17)0.0601 (16)0.0193 (16)0.0048 (15)0.0053 (13)
C70.084 (2)0.088 (2)0.0758 (19)0.0364 (18)0.0124 (16)0.0035 (16)
C80.0663 (17)0.0726 (18)0.0681 (17)0.0130 (13)0.0174 (13)0.0053 (13)
C90.0360 (10)0.0371 (11)0.0462 (12)0.0018 (8)0.0006 (9)0.0015 (9)
C100.0427 (12)0.0605 (14)0.0470 (13)0.0016 (10)0.0025 (10)0.0043 (10)
C110.0347 (12)0.0830 (17)0.0642 (16)0.0008 (11)0.0079 (11)0.0086 (13)
C120.0335 (12)0.0918 (19)0.0674 (17)0.0053 (12)0.0092 (11)0.0139 (14)
C130.0476 (13)0.0662 (15)0.0500 (13)0.0069 (11)0.0083 (11)0.0080 (11)
C140.0360 (11)0.0476 (12)0.0435 (12)0.0046 (9)0.0004 (9)0.0022 (9)
C150.0489 (12)0.0590 (14)0.0394 (12)0.0133 (11)0.0069 (10)0.0066 (10)
C160.0681 (16)0.0558 (15)0.0622 (15)0.0101 (12)0.0007 (12)0.0043 (12)
C170.113 (3)0.0540 (17)0.086 (2)0.0182 (16)0.0076 (19)0.0043 (14)
C180.092 (2)0.083 (2)0.088 (2)0.0443 (18)0.0201 (18)0.0323 (18)
C190.0768 (19)0.097 (2)0.0630 (17)0.0370 (17)0.0086 (14)0.0254 (16)
C200.0581 (14)0.0802 (17)0.0471 (13)0.0148 (13)0.0009 (11)0.0107 (12)
C210.0491 (13)0.0673 (15)0.0473 (13)0.0062 (12)0.0043 (10)0.0060 (12)
C220.0755 (18)0.091 (2)0.0469 (15)0.0106 (15)0.0085 (13)0.0012 (13)
C230.0714 (18)0.123 (3)0.0512 (16)0.0050 (18)0.0115 (13)0.0022 (17)
C240.114 (3)0.154 (4)0.067 (2)0.022 (3)0.0348 (19)0.042 (2)
C250.161 (4)0.100 (3)0.105 (3)0.024 (3)0.047 (3)0.047 (2)
C260.150 (3)0.088 (2)0.090 (2)0.019 (2)0.061 (2)0.0298 (18)
C270.0638 (15)0.0481 (13)0.0483 (13)0.0064 (11)0.0064 (11)0.0051 (10)
C280.0780 (18)0.0604 (16)0.0767 (18)0.0021 (14)0.0118 (14)0.0049 (14)
C290.111 (3)0.0569 (18)0.090 (2)0.0035 (18)0.029 (2)0.0093 (16)
C300.145 (3)0.069 (2)0.076 (2)0.039 (2)0.041 (2)0.0141 (17)
C310.138 (3)0.115 (3)0.084 (2)0.073 (3)0.012 (2)0.006 (2)
C320.104 (2)0.0723 (18)0.0711 (18)0.0271 (17)0.0163 (17)0.0026 (14)
C330.0479 (12)0.0562 (14)0.0450 (12)0.0088 (11)0.0031 (10)0.0020 (10)
C340.0757 (18)0.0842 (19)0.0491 (15)0.0040 (14)0.0061 (13)0.0033 (13)
C350.094 (2)0.111 (3)0.0451 (15)0.014 (2)0.0128 (14)0.0116 (16)
C360.092 (2)0.097 (2)0.075 (2)0.0012 (19)0.0113 (17)0.0382 (18)
C370.091 (2)0.0646 (17)0.077 (2)0.0046 (15)0.0014 (16)0.0201 (15)
C380.0625 (15)0.0575 (15)0.0546 (14)0.0037 (12)0.0040 (11)0.0075 (12)
C390.0560 (14)0.0681 (16)0.0477 (13)0.0055 (12)0.0069 (11)0.0069 (11)
C400.0454 (13)0.0728 (16)0.0492 (13)0.0041 (11)0.0100 (10)0.0038 (11)
C410.0444 (12)0.0579 (14)0.0522 (13)0.0032 (11)0.0103 (10)0.0022 (11)
C420.0787 (18)0.0628 (17)0.0718 (18)0.0018 (14)0.0072 (14)0.0117 (13)
C430.115 (3)0.0577 (17)0.082 (2)0.0130 (17)0.0013 (18)0.0129 (14)
C440.091 (2)0.083 (2)0.108 (3)0.0334 (19)0.018 (2)0.0008 (19)
C450.0572 (18)0.085 (2)0.141 (3)0.0117 (16)0.0014 (18)0.010 (2)
C460.0510 (15)0.0648 (17)0.104 (2)0.0061 (13)0.0028 (14)0.0014 (15)
C470.0409 (12)0.0489 (12)0.0554 (13)0.0004 (10)0.0021 (10)0.0018 (10)
C480.0484 (14)0.0686 (17)0.0848 (18)0.0083 (12)0.0186 (13)0.0168 (14)
C490.0475 (14)0.0739 (18)0.099 (2)0.0160 (13)0.0126 (14)0.0011 (16)
C500.0646 (16)0.0532 (14)0.0797 (18)0.0089 (13)0.0098 (14)0.0012 (13)
C510.0692 (17)0.0595 (16)0.0702 (17)0.0003 (13)0.0050 (14)0.0128 (13)
C520.0503 (13)0.0614 (15)0.0548 (14)0.0054 (11)0.0053 (11)0.0049 (11)
C530.095 (2)0.085 (2)0.124 (3)0.002 (2)0.023 (2)0.008 (2)
C54A0.122 (9)0.263 (15)0.195 (13)0.032 (9)0.013 (8)0.081 (13)
Cl1A0.159 (3)0.172 (3)0.267 (4)0.043 (2)0.016 (3)0.060 (3)
Cl2A0.207 (4)0.462 (9)0.195 (4)0.047 (6)0.012 (3)0.067 (5)
C550.230 (9)0.196 (8)0.416 (15)0.034 (6)0.002 (9)0.029 (8)
C560.175 (6)0.245 (8)0.241 (8)0.032 (6)0.006 (5)0.001 (6)
C570.217 (10)0.264 (11)0.179 (6)0.084 (8)0.020 (6)0.001 (8)
Geometric parameters (Å, º) top
Pd1—C92.0783 (19)C27—C281.384 (3)
Pd1—C12.1711 (19)C28—C291.378 (4)
Pd1—P22.2783 (6)C28—H280.9300
Pd1—P32.3554 (6)C29—C301.351 (4)
S1—O41.413 (2)C29—H290.9300
S1—O51.414 (2)C30—C311.348 (5)
S1—O61.466 (3)C30—H300.9300
S1—C531.777 (4)C31—C321.389 (4)
P1—C11.768 (2)C31—H310.9300
P1—C141.783 (2)C32—H320.9300
P1—C211.797 (2)C33—C381.379 (3)
P1—C151.800 (2)C33—C341.402 (3)
P3—C411.818 (2)C34—C351.367 (4)
P3—C471.819 (2)C34—H340.9300
P3—C401.834 (2)C35—C361.356 (4)
P2—C331.814 (2)C35—H350.9300
P2—C271.817 (2)C36—C371.352 (4)
P2—C391.834 (2)C36—H360.9300
O1—C21.218 (2)C37—C381.378 (3)
O2—N11.182 (4)C37—H370.9300
O3—N11.159 (4)C38—H380.9300
F1—C531.346 (4)C39—C401.517 (3)
F2—C531.332 (4)C39—H39A0.9700
F3—C531.324 (4)C39—H39B0.9700
N1—C61.512 (4)C40—H40A0.9700
C1—C21.471 (3)C40—H40B0.9700
C1—H10.9800C41—C461.378 (3)
C2—C31.504 (3)C41—C421.381 (3)
C3—C41.383 (3)C42—C431.397 (4)
C3—C81.397 (3)C42—H420.9300
C4—C51.392 (3)C43—C441.358 (4)
C4—H40.9300C43—H430.9300
C5—C61.334 (4)C44—C451.376 (4)
C5—H50.9300C44—H440.9300
C6—C71.361 (4)C45—C461.377 (4)
C7—C81.375 (4)C45—H450.9300
C7—H70.9300C46—H460.9300
C8—H80.9300C47—C521.381 (3)
C9—C101.397 (3)C47—C481.390 (3)
C9—C141.405 (3)C48—C491.368 (3)
C10—C111.378 (3)C48—H480.9300
C10—H100.9300C49—C501.383 (4)
C11—C121.363 (3)C49—H490.9300
C11—H110.9300C50—C511.352 (3)
C12—C131.380 (3)C50—H500.9300
C12—H120.9300C51—C521.378 (3)
C13—C141.378 (3)C51—H510.9300
C13—H130.9300C52—H520.9300
C15—C161.379 (3)C54A—Cl1A1.726 (8)
C15—C201.389 (3)C54A—Cl2A1.730 (8)
C16—C171.394 (3)C54A—H54A0.9700
C16—H160.9300C54A—H54B0.9700
C17—C181.370 (4)C54B—Cl2B1.746 (9)
C17—H170.9300C54B—Cl1B1.787 (9)
C18—C191.361 (4)C54B—H54C0.9700
C18—H180.9300C54B—H54D0.9700
C19—C201.381 (3)C54C—Cl2C1.744 (10)
C19—H190.9300C54C—Cl1C1.778 (10)
C20—H200.9300C54C—H54E0.9700
C21—C261.352 (4)C54C—H54F0.9700
C21—C221.386 (3)C55—C561.472 (6)
C22—C231.384 (4)C55—H55A0.9600
C22—H220.9300C55—H55B0.9600
C23—C241.310 (4)C55—H55C0.9600
C23—H230.9300C56—C571.523 (7)
C24—C251.357 (5)C56—H56A0.9700
C24—H240.9300C56—H56B0.9700
C25—C261.401 (4)C57—C57i1.455 (8)
C25—H250.9300C57—H57A0.9700
C26—H260.9300C57—H57B0.9700
C27—C321.375 (3)
C9—Pd1—C183.17 (8)C30—C29—C28120.0 (3)
C9—Pd1—P292.50 (6)C30—C29—H29120.0
C1—Pd1—P2175.31 (5)C28—C29—H29120.0
C9—Pd1—P3175.68 (5)C31—C30—C29120.6 (3)
C1—Pd1—P3100.49 (5)C31—C30—H30119.7
P2—Pd1—P383.91 (2)C29—C30—H30119.7
O4—S1—O5116.71 (16)C30—C31—C32120.7 (3)
O4—S1—O6112.71 (18)C30—C31—H31119.7
O5—S1—O6114.10 (17)C32—C31—H31119.7
O4—S1—C53104.18 (18)C27—C32—C31119.5 (3)
O5—S1—C53104.67 (17)C27—C32—H32120.3
O6—S1—C53102.43 (19)C31—C32—H32120.3
C1—P1—C14100.26 (9)C38—C33—C34118.5 (2)
C1—P1—C21114.63 (11)C38—C33—P2120.54 (17)
C14—P1—C21110.91 (10)C34—C33—P2120.85 (19)
C1—P1—C15116.56 (10)C35—C34—C33119.5 (3)
C14—P1—C15108.63 (10)C35—C34—H34120.2
C21—P1—C15105.72 (10)C33—C34—H34120.2
C41—P3—C47106.47 (10)C36—C35—C34120.7 (3)
C41—P3—C40103.43 (10)C36—C35—H35119.6
C47—P3—C40101.05 (10)C34—C35—H35119.6
C41—P3—Pd1123.64 (7)C37—C36—C35120.8 (3)
C47—P3—Pd1114.05 (7)C37—C36—H36119.6
C40—P3—Pd1105.28 (7)C35—C36—H36119.6
C33—P2—C27108.75 (10)C36—C37—C38119.9 (3)
C33—P2—C39102.42 (11)C36—C37—H37120.0
C27—P2—C39104.28 (11)C38—C37—H37120.0
C33—P2—Pd1113.60 (7)C37—C38—C33120.5 (2)
C27—P2—Pd1117.51 (7)C37—C38—H38119.8
C39—P2—Pd1108.79 (8)C33—C38—H38119.8
O3—N1—O2126.6 (4)C40—C39—P2107.48 (15)
O3—N1—C6117.0 (4)C40—C39—H39A110.2
O2—N1—C6116.4 (3)P2—C39—H39A110.2
C2—C1—P1118.04 (15)C40—C39—H39B110.2
C2—C1—Pd1119.69 (14)P2—C39—H39B110.2
P1—C1—Pd199.62 (9)H39A—C39—H39B108.5
C2—C1—H1106.1C39—C40—P3107.53 (15)
P1—C1—H1106.1C39—C40—H40A110.2
Pd1—C1—H1106.1P3—C40—H40A110.2
O1—C2—C1122.1 (2)C39—C40—H40B110.2
O1—C2—C3119.31 (19)P3—C40—H40B110.2
C1—C2—C3118.59 (19)H40A—C40—H40B108.5
C4—C3—C8118.1 (2)C46—C41—C42118.7 (2)
C4—C3—C2124.1 (2)C46—C41—P3123.39 (19)
C8—C3—C2117.8 (2)C42—C41—P3117.94 (18)
C3—C4—C5120.6 (2)C41—C42—C43120.0 (3)
C3—C4—H4119.7C41—C42—H42120.0
C5—C4—H4119.7C43—C42—H42120.0
C6—C5—C4119.0 (3)C44—C43—C42120.0 (3)
C6—C5—H5120.5C44—C43—H43120.0
C4—C5—H5120.5C42—C43—H43120.0
C5—C6—C7122.8 (3)C43—C44—C45120.7 (3)
C5—C6—N1118.5 (3)C43—C44—H44119.6
C7—C6—N1118.7 (3)C45—C44—H44119.6
C6—C7—C8119.0 (3)C44—C45—C46119.1 (3)
C6—C7—H7120.5C44—C45—H45120.4
C8—C7—H7120.5C46—C45—H45120.4
C7—C8—C3120.5 (3)C45—C46—C41121.5 (3)
C7—C8—H8119.7C45—C46—H46119.3
C3—C8—H8119.7C41—C46—H46119.3
C10—C9—C14115.00 (18)C52—C47—C48117.5 (2)
C10—C9—Pd1128.35 (16)C52—C47—P3120.37 (16)
C14—C9—Pd1116.65 (14)C48—C47—P3121.90 (17)
C11—C10—C9121.6 (2)C49—C48—C47121.1 (2)
C11—C10—H10119.2C49—C48—H48119.4
C9—C10—H10119.2C47—C48—H48119.4
C12—C11—C10121.6 (2)C48—C49—C50120.5 (2)
C12—C11—H11119.2C48—C49—H49119.8
C10—C11—H11119.2C50—C49—H49119.8
C11—C12—C13119.3 (2)C51—C50—C49118.7 (2)
C11—C12—H12120.4C51—C50—H50120.7
C13—C12—H12120.4C49—C50—H50120.7
C14—C13—C12119.0 (2)C50—C51—C52121.5 (2)
C14—C13—H13120.5C50—C51—H51119.2
C12—C13—H13120.5C52—C51—H51119.2
C13—C14—C9123.56 (19)C51—C52—C47120.6 (2)
C13—C14—P1124.16 (16)C51—C52—H52119.7
C9—C14—P1112.28 (14)C47—C52—H52119.7
C16—C15—C20119.9 (2)F3—C53—F2105.1 (3)
C16—C15—P1120.01 (17)F3—C53—F1109.0 (3)
C20—C15—P1120.12 (19)F2—C53—F1109.5 (3)
C15—C16—C17119.1 (2)F3—C53—S1112.8 (3)
C15—C16—H16120.4F2—C53—S1110.9 (3)
C17—C16—H16120.4F1—C53—S1109.4 (3)
C18—C17—C16120.3 (3)Cl1A—C54A—Cl2A106.1 (6)
C18—C17—H17119.8Cl1A—C54A—H54A110.5
C16—C17—H17119.8Cl2A—C54A—H54A110.5
C19—C18—C17120.6 (3)Cl1A—C54A—H54B110.5
C19—C18—H18119.7Cl2A—C54A—H54B110.5
C17—C18—H18119.7H54A—C54A—H54B108.7
C18—C19—C20120.0 (3)Cl2B—C54B—Cl1B106.2 (8)
C18—C19—H19120.0Cl2B—C54B—H54C110.5
C20—C19—H19120.0Cl1B—C54B—H54C110.5
C19—C20—C15120.1 (3)Cl2B—C54B—H54D110.5
C19—C20—H20120.0Cl1B—C54B—H54D110.5
C15—C20—H20120.0H54C—C54B—H54D108.7
C26—C21—C22118.4 (2)Cl2C—C54C—Cl1C96.1 (7)
C26—C21—P1120.5 (2)Cl2C—C54C—H54E112.5
C22—C21—P1121.1 (2)Cl1C—C54C—H54E112.5
C23—C22—C21120.6 (3)Cl2C—C54C—H54F112.5
C23—C22—H22119.7Cl1C—C54C—H54F112.5
C21—C22—H22119.7H54E—C54C—H54F110.1
C24—C23—C22120.6 (3)C56—C55—H55A109.5
C24—C23—H23119.7C56—C55—H55B109.5
C22—C23—H23119.7H55A—C55—H55B109.5
C23—C24—C25120.1 (3)C56—C55—H55C109.5
C23—C24—H24119.9H55A—C55—H55C109.5
C25—C24—H24119.9H55B—C55—H55C109.5
C24—C25—C26120.6 (3)C55—C56—C57112.2 (6)
C24—C25—H25119.7C55—C56—H56A109.2
C26—C25—H25119.7C57—C56—H56A109.2
C21—C26—C25119.3 (3)C55—C56—H56B109.2
C21—C26—H26120.3C57—C56—H56B109.2
C25—C26—H26120.3H56A—C56—H56B107.9
C32—C27—C28118.8 (2)C57i—C57—C56123.4 (9)
C32—C27—P2123.8 (2)C57i—C57—H57A106.5
C28—C27—P2117.34 (19)C56—C57—H57A106.5
C29—C28—C27120.4 (3)C57i—C57—H57B106.5
C29—C28—H28119.8C56—C57—H57B106.5
C27—C28—H28119.8H57A—C57—H57B106.5
Symmetry code: (i) x, y+1, z.
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
C19—H19···O1ii0.932.543.284 (3)138
C30—H30···O6iii0.932.553.372 (4)148
C39—H39B···O6iv0.972.593.309 (4)131
Symmetry codes: (ii) x+1, y, z; (iii) x, y1, z; (iv) x+3/2, y1/2, z+1/2.

Experimental details

Crystal data
Chemical formula[Pd(C26H19NO3P)(C26H24P2)]CF3O3S·CH2Cl2·0.5C6H14
Mr1206.27
Crystal system, space groupMonoclinic, P21/n
Temperature (K)294
a, b, c (Å)12.4063 (7), 14.2445 (8), 31.3633 (17)
β (°) 91.6675 (9)
V3)5540.2 (5)
Z4
Radiation typeMo Kα
µ (mm1)0.62
Crystal size (mm)0.19 × 0.16 × 0.10
Data collection
DiffractometerBruker APEXII CCD
diffractometer
Absorption correctionMulti-scan
(SADABS; Bruker, 2008)
Tmin, Tmax0.872, 0.955
No. of measured, independent and
observed [I > 2σ(I)] reflections
62924, 10529, 8106
Rint0.036
(sin θ/λ)max1)0.610
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.029, 0.076, 1.04
No. of reflections10529
No. of parameters691
No. of restraints14
H-atom treatmentH-atom parameters constrained
Δρmax, Δρmin (e Å3)0.37, 0.38

Computer programs: APEX2 (Bruker, 2008), SAINT (Bruker, 2008), SIR97 (Altomare et al., 1999), ORTEP-3 for Windows (Farrugia, 1997) and SCHAKAL97 (Keller, 1997), SHELXL97 (Sheldrick, 2008) and PARST95 (Nardelli, 1995).

Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
C19—H19···O1i0.932.543.284 (3)138
C30—H30···O6ii0.932.553.372 (4)148
C39—H39B···O6iii0.972.593.309 (4)131
Symmetry codes: (i) x+1, y, z; (ii) x, y1, z; (iii) x+3/2, y1/2, z+1/2.
 

Acknowledgements

Financial support from the Universitá degli Studi di Parma is gratefully acknowledged.

References

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Volume 67| Part 4| April 2011| Pages m416-m417
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