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Acta Crystallogr Sect E Struct Rep Online. 2008 July 1; 64(Pt 7): m907–m908.
Published online 2008 June 13. doi:  10.1107/S1600536808017005
PMCID: PMC2961759

Bis[2-phenyl-1-(phenyl­iminio)isoindo­line] di-μ-chlorido-bis­[dichloridopalladate(II)] benzene disolvate

Abstract

In the title compound, (C20H17N2)2[Pd2Cl6]·2C6H6, the dichloride-bridged [Pd2Cl6]2− anion lies across an inversion center with each PdII ion in a slightly distorted square-planar environment. In the crystal structure, two cations and an anion are connected via N—H(...)Cl hydrogen bonds between the NH groups of the iminioisoindoline cations and terminal Cl atoms of a hexa­chloridodipalladate(II) anion. The Pd—Cl distance of the terminal chloride engaged in hydrogen bonding is slightly longer than the Pd—Cl distance of the adjacent terminal chloride which is not involved in hydrogen bonding.

Related literature

For related literature, see: Bartczak et al. (2001 [triangle]); Chitanda et al. (2008 [triangle]); Fábry et al. (2004 [triangle]); Lassahn et al. (2003 [triangle]); Ojwach et al. (2007 [triangle]); Schupp et al. (2001 [triangle]); Yang et al. (2008 [triangle]).

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Object name is e-64-0m907-scheme1.jpg

Experimental

Crystal data

  • (C20H17N2)2[Pd2Cl6]·2C6H6
  • M r = 1152.46
  • Triclinic, An external file that holds a picture, illustration, etc.
Object name is e-64-0m907-efi1.jpg
  • a = 9.5457 (3) Å
  • b = 9.9754 (3) Å
  • c = 14.8002 (5) Å
  • α = 74.270 (2)°
  • β = 80.615 (2)°
  • γ = 63.228 (2)°
  • V = 1209.74 (7) Å3
  • Z = 1
  • Mo Kα radiation
  • μ = 1.11 mm−1
  • T = 173 (2) K
  • 0.22 × 0.18 × 0.05 mm

Data collection

  • Bruker–Nonius KappaCCD diffractometer
  • Absorption correction: ψ scan (SHELXTL; Sheldrick, 2008 [triangle]) T min = 0.791, T max = 0.946
  • 18458 measured reflections
  • 6458 independent reflections
  • 5322 reflections with I > 2σ(I)
  • R int = 0.038

Refinement

  • R[F 2 > 2σ(F 2)] = 0.039
  • wR(F 2) = 0.094
  • S = 1.04
  • 6458 reflections
  • 290 parameters
  • H-atom parameters constrained
  • Δρmax = 0.82 e Å−3
  • Δρmin = −0.94 e Å−3

Data collection: COLLECT (Nonius, 1998 [triangle]); cell refinement: SCALEPACK (Otwinowski & Minor, 1997 [triangle]); data reduction: DENZO (Otwinowski & Minor 1997 [triangle]) and SCALEPACK; program(s) used to solve structure: SIR97 (Altomare et al., 1999 [triangle]); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 [triangle]); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997 [triangle]); software used to prepare material for publication: SHELXL97.

Table 1
Selected geometric parameters (Å, °)
Table 2
Hydrogen-bond geometry (Å, °)

Supplementary Material

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536808017005/lh2628sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536808017005/lh2628Isup2.hkl

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

Acknowledgments

Financial assistance for this project was provided by the Natural Sciences and Engineering Research Council of Canada (NSERC) for an operating grant to SRF, and by the Canadian Government through the Commonwealth Scholarship fund for JMC.

supplementary crystallographic information

Comment

As part of the ongoing research in our laboratory directed at the synthesis of substituted palladacycles incorporating iminoisoindolines (Chitanda et al., 2008), the title compound, I, was obtained by reaction of 1-phenylimino-2-phenylisoindoline with dichloropalladium(II) in the presence of HCl. The bis-iminoisoindolinium hexachlorodipalladate complex crystallizes with two molecules of benzene in the unit cell of the triclinic space group P1. The crystal structure of I is stabilized by a system of intermolecular hydrogen bonds between the imine NH atoms of the iminoisoindolinium cation and the termininal chloride atoms in the hexachlorodipalladate(II) anion. The Pd2Cl62- anion lies across an inversion center and has the expected planar dichloro-bridged structure with the Pd—Cl distance of the terminal chloride engaged in hydrogen bonding being slightly longer at 2.2929 (7)Å than the Pd—Cl distance of the adjacent terminal chloride at 2.2635 (7)Å which does not show any H-bonding. In previously reported structures incorporating a Pd2Cl62- anion, the anion most often lies across an inversion center (Bartczak et al., 2001; Fábry et al., 2004; Lassahn et al., 2003; Ojwach et al., 2007; Schupp et al., 2001; Yang et al., 2008). The molecular structure and packing of the title compound is shown in Figs. 1 and 2.

Experimental

The title compound was synthesized by reaction of 1-phenylimino-2- phenylisoindoline with dichloropalladium(II) in the presence of HCl in dichloromethane. Single crystals were obtained by slow evaporation from a benzene solution at ambient temperature.

Refinement

H atoms were placed in calculated positions with Uiso constrained to be 1.2 times Ueq of the carrier atom for all hydrogen atoms.

Figures

Fig. 1.
Molecular structure of the title compound with thermal ellipsoids at the 50% probability level. H atoms not participating in H-bonding are omitted for clarity. Only the symmetry unique cation is shown [symmetry code: (i) -x, -y+2, z].
Fig. 2.
Packing of the title compound with hydrogen bonds shown with dashed lines. H atoms not participating in H-bonding are omitted for clarity.

Crystal data

(C20H17N2)2[Pd2Cl6]·2C6H6Z = 1
Mr = 1152.46F000 = 580
Triclinic, P1Dx = 1.582 Mg m3
Hall symbol: -P 1Mo Kα radiation λ = 0.71073 Å
a = 9.5457 (3) ÅCell parameters from 5512 reflections
b = 9.9754 (3) Åθ = 1.0–29.1º
c = 14.8002 (5) ŵ = 1.12 mm1
α = 74.270 (2)ºT = 173 (2) K
β = 80.615 (2)ºPlate, orange
γ = 63.228 (2)º0.22 × 0.18 × 0.05 mm
V = 1209.74 (7) Å3

Data collection

Bruker–Nonius KappaCCD diffractometer6458 independent reflections
Radiation source: fine-focus sealed tube5322 reflections with I > 2σ(I)
Monochromator: horizonally mounted graphite crystalRint = 0.038
Detector resolution: 9 pixels mm-1θmax = 29.1º
T = 173(2) Kθmin = 2.9º
[var phi] scans and ω scans with κ offsetsh = −13→11
Absorption correction: ψ scan(SHELXTL; Sheldrick, 2008)k = −13→13
Tmin = 0.791, Tmax = 0.946l = −20→20
18458 measured reflections

Refinement

Refinement on F2Hydrogen site location: inferred from neighbouring sites
Least-squares matrix: fullH-atom parameters constrained
R[F2 > 2σ(F2)] = 0.039  w = 1/[σ2(Fo2) + (0.0328P)2 + 1.4367P] where P = (Fo2 + 2Fc2)/3
wR(F2) = 0.094(Δ/σ)max < 0.001
S = 1.04Δρmax = 0.82 e Å3
6458 reflectionsΔρmin = −0.94 e Å3
290 parametersExtinction correction: SHELXL97 (Sheldrick, 2008), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
Primary atom site location: structure-invariant direct methodsExtinction coefficient: 0.0061 (7)
Secondary atom site location: difference Fourier map

Special details

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)

xyzUiso*/Ueq
Pd10.00603 (2)0.87175 (2)0.103892 (15)0.02846 (8)
Cl10.05538 (8)0.85027 (8)0.25493 (5)0.03459 (15)
Cl2−0.03111 (9)0.65391 (8)0.14749 (5)0.03895 (17)
Cl30.04870 (8)1.09399 (8)0.05063 (5)0.03515 (15)
N10.5133 (2)0.3157 (3)0.18312 (15)0.0261 (4)
N20.3165 (2)0.4983 (2)0.26541 (15)0.0263 (4)
H20.25040.59640.25590.032*
C10.4296 (3)0.4577 (3)0.19937 (17)0.0243 (5)
C20.4887 (3)0.5622 (3)0.13560 (18)0.0284 (5)
C30.4427 (4)0.7181 (4)0.1276 (2)0.0355 (6)
H30.35290.77680.16190.043*
C40.5329 (4)0.7844 (4)0.0678 (2)0.0435 (7)
H40.50490.89080.06080.052*
C50.6646 (4)0.6971 (4)0.0176 (2)0.0471 (8)
H50.72540.7453−0.02230.057*
C60.7087 (4)0.5426 (4)0.0246 (2)0.0418 (7)
H60.79790.4843−0.01030.050*
C70.6181 (3)0.4753 (3)0.08448 (19)0.0317 (6)
C80.6411 (3)0.3118 (3)0.1107 (2)0.0332 (6)
H8A0.62990.27870.05600.040*
H8B0.74550.24210.13660.040*
C90.4809 (3)0.1840 (3)0.21669 (18)0.0267 (5)
C100.3283 (3)0.1986 (3)0.22435 (19)0.0300 (5)
H100.24330.29720.20720.036*
C110.3010 (4)0.0682 (4)0.2573 (2)0.0381 (6)
H110.19670.07700.26400.046*
C120.4264 (4)−0.0752 (4)0.2804 (2)0.0428 (7)
H120.4072−0.16430.30370.051*
C130.5781 (4)−0.0902 (3)0.2699 (2)0.0425 (7)
H130.6633−0.18940.28400.051*
C140.6063 (3)0.0394 (3)0.2387 (2)0.0352 (6)
H140.71090.02990.23240.042*
C150.2902 (3)0.4009 (3)0.34982 (17)0.0233 (5)
C160.4162 (3)0.2904 (3)0.40237 (18)0.0269 (5)
H160.52010.27800.38210.032*
C170.3886 (3)0.1979 (3)0.4851 (2)0.0338 (6)
H170.47430.12120.52160.041*
C180.2376 (4)0.2166 (4)0.5149 (2)0.0379 (6)
H180.21980.15190.57130.045*
C190.1122 (3)0.3291 (4)0.4628 (2)0.0381 (7)
H190.00830.34220.48390.046*
C200.1372 (3)0.4233 (3)0.3796 (2)0.0314 (6)
H200.05120.50140.34390.038*
C210.6984 (4)0.4602 (4)0.4106 (3)0.0488 (8)
H210.64320.56410.41670.059*
C220.7139 (4)0.3430 (4)0.4878 (3)0.0457 (8)
H220.66990.36600.54720.055*
C230.7927 (4)0.1921 (4)0.4801 (3)0.0455 (8)
H230.80310.11100.53380.055*
C240.8565 (4)0.1594 (4)0.3940 (3)0.0480 (8)
H240.91100.05530.38830.058*
C250.8418 (4)0.2765 (5)0.3164 (3)0.0532 (9)
H250.88620.25350.25710.064*
C260.7618 (4)0.4292 (5)0.3246 (3)0.0523 (9)
H260.75140.51090.27120.063*

Atomic displacement parameters (Å2)

U11U22U33U12U13U23
Pd10.02505 (11)0.02529 (12)0.03109 (13)−0.00905 (8)−0.00203 (8)−0.00290 (8)
Cl10.0361 (3)0.0310 (3)0.0325 (3)−0.0106 (3)−0.0012 (3)−0.0077 (3)
Cl20.0451 (4)0.0345 (4)0.0398 (4)−0.0227 (3)−0.0061 (3)0.0001 (3)
Cl30.0404 (4)0.0322 (3)0.0349 (4)−0.0187 (3)−0.0071 (3)−0.0019 (3)
N10.0222 (10)0.0309 (11)0.0263 (11)−0.0128 (9)0.0024 (8)−0.0077 (9)
N20.0240 (10)0.0234 (10)0.0266 (11)−0.0076 (8)0.0017 (8)−0.0045 (8)
C10.0226 (11)0.0292 (12)0.0228 (12)−0.0124 (10)−0.0016 (9)−0.0058 (10)
C20.0307 (13)0.0370 (14)0.0221 (12)−0.0210 (11)−0.0017 (10)−0.0016 (10)
C30.0442 (16)0.0407 (16)0.0283 (14)−0.0262 (14)0.0002 (12)−0.0045 (12)
C40.066 (2)0.0516 (19)0.0290 (15)−0.0426 (17)−0.0017 (14)−0.0026 (13)
C50.061 (2)0.075 (2)0.0286 (15)−0.053 (2)0.0020 (14)−0.0060 (15)
C60.0392 (16)0.068 (2)0.0314 (15)−0.0353 (16)0.0045 (12)−0.0124 (14)
C70.0310 (13)0.0457 (16)0.0257 (13)−0.0222 (12)0.0001 (10)−0.0100 (12)
C80.0266 (13)0.0446 (16)0.0312 (14)−0.0168 (12)0.0067 (11)−0.0145 (12)
C90.0309 (13)0.0267 (12)0.0231 (12)−0.0122 (11)−0.0012 (10)−0.0069 (10)
C100.0305 (13)0.0334 (14)0.0291 (13)−0.0158 (11)−0.0002 (10)−0.0087 (11)
C110.0462 (17)0.0453 (17)0.0333 (15)−0.0279 (14)0.0031 (13)−0.0128 (13)
C120.069 (2)0.0345 (15)0.0322 (15)−0.0291 (15)0.0032 (14)−0.0091 (12)
C130.0541 (19)0.0277 (14)0.0371 (16)−0.0095 (13)−0.0034 (14)−0.0075 (12)
C140.0335 (14)0.0338 (14)0.0334 (15)−0.0079 (12)−0.0008 (11)−0.0119 (12)
C150.0239 (11)0.0238 (11)0.0218 (11)−0.0102 (9)0.0020 (9)−0.0063 (9)
C160.0230 (11)0.0279 (12)0.0283 (13)−0.0088 (10)−0.0011 (10)−0.0079 (10)
C170.0376 (15)0.0306 (14)0.0286 (14)−0.0117 (12)−0.0057 (11)−0.0023 (11)
C180.0493 (17)0.0413 (16)0.0288 (14)−0.0287 (14)0.0013 (12)−0.0017 (12)
C190.0328 (14)0.0503 (18)0.0358 (15)−0.0254 (14)0.0069 (12)−0.0079 (13)
C200.0234 (12)0.0349 (14)0.0321 (14)−0.0103 (11)0.0003 (10)−0.0062 (11)
C210.0351 (16)0.0365 (17)0.079 (3)−0.0153 (14)−0.0067 (16)−0.0175 (17)
C220.0331 (15)0.064 (2)0.0496 (19)−0.0235 (15)0.0041 (14)−0.0259 (17)
C230.0314 (15)0.0464 (18)0.056 (2)−0.0190 (14)−0.0093 (14)0.0010 (15)
C240.0276 (14)0.0388 (17)0.078 (3)−0.0059 (13)−0.0101 (15)−0.0242 (17)
C250.0315 (15)0.089 (3)0.047 (2)−0.0249 (18)0.0012 (14)−0.031 (2)
C260.0394 (17)0.059 (2)0.058 (2)−0.0292 (17)−0.0142 (16)0.0092 (17)

Geometric parameters (Å, °)

Pd1—Cl22.2635 (7)C11—C121.386 (5)
Pd1—Cl12.2929 (7)C11—H110.9500
Pd1—Cl3i2.3292 (7)C12—C131.374 (5)
Pd1—Cl32.3374 (7)C12—H120.9500
Pd1—Pd1i3.4060 (4)C13—C141.381 (4)
Cl3—Pd1i2.3292 (7)C13—H130.9500
N1—C11.343 (3)C14—H140.9500
N1—C91.426 (3)C15—C161.383 (3)
N1—C81.481 (3)C15—C201.388 (3)
N2—C11.327 (3)C16—C171.386 (4)
N2—C151.424 (3)C16—H160.9500
N2—H20.8800C17—C181.380 (4)
C1—C21.456 (4)C17—H170.9500
C2—C31.388 (4)C18—C191.382 (4)
C2—C71.391 (4)C18—H180.9500
C3—C41.381 (4)C19—C201.390 (4)
C3—H30.9500C19—H190.9500
C4—C51.397 (5)C20—H200.9500
C4—H40.9500C21—C221.367 (5)
C5—C61.381 (5)C21—C261.369 (5)
C5—H50.9500C21—H210.9500
C6—C71.391 (4)C22—C231.374 (5)
C6—H60.9500C22—H220.9500
C7—C81.490 (4)C23—C241.377 (5)
C8—H8A0.9900C23—H230.9500
C8—H8B0.9900C24—C251.371 (5)
C9—C101.385 (4)C24—H240.9500
C9—C141.392 (4)C25—C261.393 (5)
C10—C111.386 (4)C25—H250.9500
C10—H100.9500C26—H260.9500
Cl2—Pd1—Cl191.32 (3)C11—C10—H10120.3
Cl2—Pd1—Cl3i91.00 (3)C10—C11—C12119.8 (3)
Cl1—Pd1—Cl3i177.33 (3)C10—C11—H11120.1
Cl2—Pd1—Cl3176.86 (3)C12—C11—H11120.1
Cl1—Pd1—Cl391.47 (3)C13—C12—C11120.9 (3)
Cl3i—Pd1—Cl386.25 (3)C13—C12—H12119.6
Cl2—Pd1—Pd1i134.20 (2)C11—C12—H12119.6
Cl1—Pd1—Pd1i134.48 (2)C12—C13—C14119.8 (3)
Cl3i—Pd1—Pd1i43.218 (17)C12—C13—H13120.1
Cl3—Pd1—Pd1i43.030 (18)C14—C13—H13120.1
Pd1i—Cl3—Pd193.75 (3)C13—C14—C9119.6 (3)
C1—N1—C9128.5 (2)C13—C14—H14120.2
C1—N1—C8111.3 (2)C9—C14—H14120.2
C9—N1—C8119.7 (2)C16—C15—C20121.3 (2)
C1—N2—C15127.3 (2)C16—C15—N2119.6 (2)
C1—N2—H2116.3C20—C15—N2119.0 (2)
C15—N2—H2116.4C15—C16—C17119.0 (2)
N2—C1—N1126.8 (2)C15—C16—H16120.5
N2—C1—C2124.2 (2)C17—C16—H16120.5
N1—C1—C2108.9 (2)C18—C17—C16120.5 (3)
C3—C2—C7122.0 (3)C18—C17—H17119.8
C3—C2—C1130.0 (3)C16—C17—H17119.8
C7—C2—C1107.7 (2)C17—C18—C19120.1 (3)
C4—C3—C2117.3 (3)C17—C18—H18120.0
C4—C3—H3121.3C19—C18—H18120.0
C2—C3—H3121.3C18—C19—C20120.4 (3)
C3—C4—C5120.9 (3)C18—C19—H19119.8
C3—C4—H4119.5C20—C19—H19119.8
C5—C4—H4119.5C15—C20—C19118.7 (3)
C6—C5—C4121.7 (3)C15—C20—H20120.6
C6—C5—H5119.2C19—C20—H20120.6
C4—C5—H5119.2C22—C21—C26120.6 (3)
C5—C6—C7117.7 (3)C22—C21—H21119.7
C5—C6—H6121.2C26—C21—H21119.7
C7—C6—H6121.2C21—C22—C23120.4 (3)
C2—C7—C6120.4 (3)C21—C22—H22119.8
C2—C7—C8109.5 (2)C23—C22—H22119.8
C6—C7—C8130.0 (3)C22—C23—C24119.6 (3)
N1—C8—C7102.4 (2)C22—C23—H23120.2
N1—C8—H8A111.3C24—C23—H23120.2
C7—C8—H8A111.3C25—C24—C23120.3 (3)
N1—C8—H8B111.3C25—C24—H24119.9
C7—C8—H8B111.3C23—C24—H24119.9
H8A—C8—H8B109.2C24—C25—C26119.9 (3)
C10—C9—C14120.6 (3)C24—C25—H25120.0
C10—C9—N1120.8 (2)C26—C25—H25120.0
C14—C9—N1118.6 (2)C21—C26—C25119.2 (3)
C9—C10—C11119.3 (3)C21—C26—H26120.4
C9—C10—H10120.3C25—C26—H26120.4
Cl1—Pd1—Cl3—Pd1i−178.61 (3)C8—N1—C9—C10−133.0 (3)
Cl3i—Pd1—Cl3—Pd1i0.0C1—N1—C9—C14−144.4 (3)
C15—N2—C1—N121.0 (4)C8—N1—C9—C1444.9 (3)
C15—N2—C1—C2−155.2 (2)C14—C9—C10—C112.1 (4)
C9—N1—C1—N215.2 (4)N1—C9—C10—C11−180.0 (2)
C8—N1—C1—N2−173.5 (2)C9—C10—C11—C12−1.2 (4)
C9—N1—C1—C2−168.2 (2)C10—C11—C12—C13−0.9 (5)
C8—N1—C1—C23.1 (3)C11—C12—C13—C142.0 (5)
N2—C1—C2—C3−1.4 (5)C12—C13—C14—C9−1.1 (4)
N1—C1—C2—C3−178.2 (3)C10—C9—C14—C13−1.0 (4)
N2—C1—C2—C7173.0 (2)N1—C9—C14—C13−178.9 (2)
N1—C1—C2—C7−3.8 (3)C1—N2—C15—C1642.8 (4)
C7—C2—C3—C4−1.3 (4)C1—N2—C15—C20−139.8 (3)
C1—C2—C3—C4172.4 (3)C20—C15—C16—C171.7 (4)
C2—C3—C4—C50.1 (5)N2—C15—C16—C17179.1 (2)
C3—C4—C5—C60.9 (5)C15—C16—C17—C18−0.4 (4)
C4—C5—C6—C7−0.7 (5)C16—C17—C18—C19−0.7 (5)
C3—C2—C7—C61.6 (4)C17—C18—C19—C200.6 (5)
C1—C2—C7—C6−173.4 (3)C16—C15—C20—C19−1.8 (4)
C3—C2—C7—C8177.9 (3)N2—C15—C20—C19−179.2 (2)
C1—C2—C7—C83.0 (3)C18—C19—C20—C150.6 (4)
C5—C6—C7—C2−0.5 (4)C26—C21—C22—C23−0.4 (5)
C5—C6—C7—C8−176.0 (3)C21—C22—C23—C240.1 (5)
C1—N1—C8—C7−1.3 (3)C22—C23—C24—C250.1 (5)
C9—N1—C8—C7170.9 (2)C23—C24—C25—C26−0.1 (5)
C2—C7—C8—N1−1.1 (3)C22—C21—C26—C250.3 (5)
C6—C7—C8—N1174.7 (3)C24—C25—C26—C21−0.1 (5)
C1—N1—C9—C1037.6 (4)

Symmetry codes: (i) −x, −y+2, −z.

Hydrogen-bond geometry (Å, °)

D—H···AD—HH···AD···AD—H···A
N2—H2···Cl10.882.373.242 (2)171

Footnotes

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: LH2628).

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