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

Chitanda, J.M.; Quail, J.W.; Foley, S.R.

doi:10.1107/S1600536808017005

metal-organic compounds

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ISSN: 2056-9890

Volume 64| Part 7| July 2008| Pages m907-m908

doi:10.1107/S1600536808017005

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

Jackson M. Chitanda,^a J. Wilson Quail ^b and Stephen R. Foley ^a ^*

^aDepartment of Chemistry, University of Saskatchewan, 110 Science Place, Saskatoon, Saskatchewan, Canada S7N 5C9, and ^bSaskatchewan Structural Sciences Centre, University of Saskatchewan, 110 Science Place, Saskatoon, Saskatchewan, Canada S7N 5C9
^*Correspondence e-mail: stephen.foley@usask.ca

(Received 13 May 2008; accepted 4 June 2008; online 13 June 2008)

In the title compound, (C₂₀H₁₇N₂)₂[Pd₂Cl₆]·2C₆H₆, the dichloride-bridged [Pd₂Cl₆]²⁻ anion lies across an inversion center with each Pd^II 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 ); Chitanda et al. (2008 ); Fábry et al. (2004 ); Lassahn et al. (2003 ); Ojwach et al. (2007 ); Schupp et al. (2001 ); Yang et al. (2008 ).

Experimental

Crystal data

(C₂₀H₁₇N₂)₂[Pd₂Cl₆]·2C₆H₆
M_r = 1152.46
Triclinic, $[P \overline 1]$
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 ) 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[F² > 2σ(F²)] = 0.039
wR(F²) = 0.094
S = 1.04
6458 reflections
290 parameters
H-atom parameters constrained
Δρ_max = 0.82 e Å⁻³
Δρ_min = −0.94 e Å⁻³

Table 1
Selected geometric parameters (Å, °)

Pd1—Cl2	2.2635 (7)
Pd1—Cl1	2.2929 (7)
Pd1—Cl3ⁱ	2.3292 (7)
Pd1—Cl3	2.3374 (7)

Cl2—Pd1—Cl1	91.32 (3)
Cl2—Pd1—Cl3ⁱ	91.00 (3)
Cl1—Pd1—Cl3ⁱ	177.33 (3)
Cl2—Pd1—Cl3	176.86 (3)
Cl1—Pd1—Cl3	91.47 (3)
Cl3ⁱ—Pd1—Cl3	86.25 (3)
Symmetry code: (i) -x, -y+2, -z.

Table 2
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N2—H2⋯Cl1	0.88	2.37	3.242 (2)	171
Symmetry codes: .

Data collection: COLLECT (Nonius, 1998 ); cell refinement: SCALEPACK (Otwinowski & Minor, 1997 ); data reduction: DENZO (Otwinowski & Minor 1997) and SCALEPACK; 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 ); software used to prepare material for publication: SHELXL97.

Supporting information

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

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

checkCIF report

Comment top

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 Pd₂Cl₆^2- 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 Pd₂Cl₆^2- 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.

Related literature top

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

Experimental top

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.

Computing details top

Data collection: COLLECT (Nonius, 1998); cell refinement: SCALEPACK (Otwinowski & Minor, 1997); data reduction: DENZO and SCALEPACK (Otwinowski & Minor 1997); 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); software used to prepare material for publication: SHELXL97 (Sheldrick, 2008).

Figures top

	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.

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

Crystal data top

(C₂₀H₁₇N₂)₂[Pd₂Cl₆]·2C₆H₆	Z = 1
M_r = 1152.46	F(000) = 580
Triclinic, P1	D_x = 1.582 Mg m⁻³
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 9.5457 (3) Å	Cell parameters from 5512 reflections
b = 9.9754 (3) Å	θ = 1.0–29.1°
c = 14.8002 (5) Å	µ = 1.12 mm⁻¹
α = 74.270 (2)°	T = 173 K
β = 80.615 (2)°	Plate, orange
γ = 63.228 (2)°	0.22 × 0.18 × 0.05 mm
V = 1209.74 (7) Å³

Data collection top

Bruker–Nonius KappaCCD diffractometer	6458 independent reflections
Radiation source: fine-focus sealed tube	5322 reflections with I > 2σ(I)
Horizonally mounted graphite crystal monochromator	R_int = 0.038
Detector resolution: 9 pixels mm^-1	θ_max = 29.1°, θ_min = 2.9°
ϕ scans and ω scans with κ offsets	h = −13→11
Absorption correction: ψ scan (SHELXTL; Sheldrick, 2008)	k = −13→13
T_min = 0.791, T_max = 0.946	l = −20→20
18458 measured reflections

Refinement top

Refinement on F²	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F² > 2σ(F²)] = 0.039	H-atom parameters constrained
wR(F²) = 0.094	w = 1/[σ²(F_o²) + (0.0328P)² + 1.4367P] where P = (F_o² + 2F_c²)/3
S = 1.04	(Δ/σ)_max < 0.001
6458 reflections	Δρ_max = 0.82 e Å⁻³
290 parameters	Δρ_min = −0.94 e Å⁻³
0 restraints	Extinction correction: SHELXL97 (Sheldrick, 2008), Fc^*=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.0061 (7)

Crystal data top

(C₂₀H₁₇N₂)₂[Pd₂Cl₆]·2C₆H₆	γ = 63.228 (2)°
M_r = 1152.46	V = 1209.74 (7) Å³
Triclinic, P1	Z = 1
a = 9.5457 (3) Å	Mo Kα radiation
b = 9.9754 (3) Å	µ = 1.12 mm⁻¹
c = 14.8002 (5) Å	T = 173 K
α = 74.270 (2)°	0.22 × 0.18 × 0.05 mm
β = 80.615 (2)°

Data collection top

Bruker–Nonius KappaCCD diffractometer	6458 independent reflections
Absorption correction: ψ scan (SHELXTL; Sheldrick, 2008)	5322 reflections with I > 2σ(I)
T_min = 0.791, T_max = 0.946	R_int = 0.038
18458 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.039	0 restraints
wR(F²) = 0.094	H-atom parameters constrained
S = 1.04	Δρ_max = 0.82 e Å⁻³
6458 reflections	Δρ_min = −0.94 e Å⁻³
290 parameters

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

	x	y	z	U_iso*/U_eq
Pd1	0.00603 (2)	0.87175 (2)	0.103892 (15)	0.02846 (8)
Cl1	0.05538 (8)	0.85027 (8)	0.25493 (5)	0.03459 (15)
Cl2	−0.03111 (9)	0.65391 (8)	0.14749 (5)	0.03895 (17)
Cl3	0.04870 (8)	1.09399 (8)	0.05063 (5)	0.03515 (15)
N1	0.5133 (2)	0.3157 (3)	0.18312 (15)	0.0261 (4)
N2	0.3165 (2)	0.4983 (2)	0.26541 (15)	0.0263 (4)
H2	0.2504	0.5964	0.2559	0.032*
C1	0.4296 (3)	0.4577 (3)	0.19937 (17)	0.0243 (5)
C2	0.4887 (3)	0.5622 (3)	0.13560 (18)	0.0284 (5)
C3	0.4427 (4)	0.7181 (4)	0.1276 (2)	0.0355 (6)
H3	0.3529	0.7768	0.1619	0.043*
C4	0.5329 (4)	0.7844 (4)	0.0678 (2)	0.0435 (7)
H4	0.5049	0.8908	0.0608	0.052*
C5	0.6646 (4)	0.6971 (4)	0.0176 (2)	0.0471 (8)
H5	0.7254	0.7453	−0.0223	0.057*
C6	0.7087 (4)	0.5426 (4)	0.0246 (2)	0.0418 (7)
H6	0.7979	0.4843	−0.0103	0.050*
C7	0.6181 (3)	0.4753 (3)	0.08448 (19)	0.0317 (6)
C8	0.6411 (3)	0.3118 (3)	0.1107 (2)	0.0332 (6)
H8A	0.6299	0.2787	0.0560	0.040*
H8B	0.7455	0.2421	0.1366	0.040*
C9	0.4809 (3)	0.1840 (3)	0.21669 (18)	0.0267 (5)
C10	0.3283 (3)	0.1986 (3)	0.22435 (19)	0.0300 (5)
H10	0.2433	0.2972	0.2072	0.036*
C11	0.3010 (4)	0.0682 (4)	0.2573 (2)	0.0381 (6)
H11	0.1967	0.0770	0.2640	0.046*
C12	0.4264 (4)	−0.0752 (4)	0.2804 (2)	0.0428 (7)
H12	0.4072	−0.1643	0.3037	0.051*
C13	0.5781 (4)	−0.0902 (3)	0.2699 (2)	0.0425 (7)
H13	0.6633	−0.1894	0.2840	0.051*
C14	0.6063 (3)	0.0394 (3)	0.2387 (2)	0.0352 (6)
H14	0.7109	0.0299	0.2324	0.042*
C15	0.2902 (3)	0.4009 (3)	0.34982 (17)	0.0233 (5)
C16	0.4162 (3)	0.2904 (3)	0.40237 (18)	0.0269 (5)
H16	0.5201	0.2780	0.3821	0.032*
C17	0.3886 (3)	0.1979 (3)	0.4851 (2)	0.0338 (6)
H17	0.4743	0.1212	0.5216	0.041*
C18	0.2376 (4)	0.2166 (4)	0.5149 (2)	0.0379 (6)
H18	0.2198	0.1519	0.5713	0.045*
C19	0.1122 (3)	0.3291 (4)	0.4628 (2)	0.0381 (7)
H19	0.0083	0.3422	0.4839	0.046*
C20	0.1372 (3)	0.4233 (3)	0.3796 (2)	0.0314 (6)
H20	0.0512	0.5014	0.3439	0.038*
C21	0.6984 (4)	0.4602 (4)	0.4106 (3)	0.0488 (8)
H21	0.6432	0.5641	0.4167	0.059*
C22	0.7139 (4)	0.3430 (4)	0.4878 (3)	0.0457 (8)
H22	0.6699	0.3660	0.5472	0.055*
C23	0.7927 (4)	0.1921 (4)	0.4801 (3)	0.0455 (8)
H23	0.8031	0.1110	0.5338	0.055*
C24	0.8565 (4)	0.1594 (4)	0.3940 (3)	0.0480 (8)
H24	0.9110	0.0553	0.3883	0.058*
C25	0.8418 (4)	0.2765 (5)	0.3164 (3)	0.0532 (9)
H25	0.8862	0.2535	0.2571	0.064*
C26	0.7618 (4)	0.4292 (5)	0.3246 (3)	0.0523 (9)
H26	0.7514	0.5109	0.2712	0.063*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Pd1	0.02505 (11)	0.02529 (12)	0.03109 (13)	−0.00905 (8)	−0.00203 (8)	−0.00290 (8)
Cl1	0.0361 (3)	0.0310 (3)	0.0325 (3)	−0.0106 (3)	−0.0012 (3)	−0.0077 (3)
Cl2	0.0451 (4)	0.0345 (4)	0.0398 (4)	−0.0227 (3)	−0.0061 (3)	0.0001 (3)
Cl3	0.0404 (4)	0.0322 (3)	0.0349 (4)	−0.0187 (3)	−0.0071 (3)	−0.0019 (3)
N1	0.0222 (10)	0.0309 (11)	0.0263 (11)	−0.0128 (9)	0.0024 (8)	−0.0077 (9)
N2	0.0240 (10)	0.0234 (10)	0.0266 (11)	−0.0076 (8)	0.0017 (8)	−0.0045 (8)
C1	0.0226 (11)	0.0292 (12)	0.0228 (12)	−0.0124 (10)	−0.0016 (9)	−0.0058 (10)
C2	0.0307 (13)	0.0370 (14)	0.0221 (12)	−0.0210 (11)	−0.0017 (10)	−0.0016 (10)
C3	0.0442 (16)	0.0407 (16)	0.0283 (14)	−0.0262 (14)	0.0002 (12)	−0.0045 (12)
C4	0.066 (2)	0.0516 (19)	0.0290 (15)	−0.0426 (17)	−0.0017 (14)	−0.0026 (13)
C5	0.061 (2)	0.075 (2)	0.0286 (15)	−0.053 (2)	0.0020 (14)	−0.0060 (15)
C6	0.0392 (16)	0.068 (2)	0.0314 (15)	−0.0353 (16)	0.0045 (12)	−0.0124 (14)
C7	0.0310 (13)	0.0457 (16)	0.0257 (13)	−0.0222 (12)	0.0001 (10)	−0.0100 (12)
C8	0.0266 (13)	0.0446 (16)	0.0312 (14)	−0.0168 (12)	0.0067 (11)	−0.0145 (12)
C9	0.0309 (13)	0.0267 (12)	0.0231 (12)	−0.0122 (11)	−0.0012 (10)	−0.0069 (10)
C10	0.0305 (13)	0.0334 (14)	0.0291 (13)	−0.0158 (11)	−0.0002 (10)	−0.0087 (11)
C11	0.0462 (17)	0.0453 (17)	0.0333 (15)	−0.0279 (14)	0.0031 (13)	−0.0128 (13)
C12	0.069 (2)	0.0345 (15)	0.0322 (15)	−0.0291 (15)	0.0032 (14)	−0.0091 (12)
C13	0.0541 (19)	0.0277 (14)	0.0371 (16)	−0.0095 (13)	−0.0034 (14)	−0.0075 (12)
C14	0.0335 (14)	0.0338 (14)	0.0334 (15)	−0.0079 (12)	−0.0008 (11)	−0.0119 (12)
C15	0.0239 (11)	0.0238 (11)	0.0218 (11)	−0.0102 (9)	0.0020 (9)	−0.0063 (9)
C16	0.0230 (11)	0.0279 (12)	0.0283 (13)	−0.0088 (10)	−0.0011 (10)	−0.0079 (10)
C17	0.0376 (15)	0.0306 (14)	0.0286 (14)	−0.0117 (12)	−0.0057 (11)	−0.0023 (11)
C18	0.0493 (17)	0.0413 (16)	0.0288 (14)	−0.0287 (14)	0.0013 (12)	−0.0017 (12)
C19	0.0328 (14)	0.0503 (18)	0.0358 (15)	−0.0254 (14)	0.0069 (12)	−0.0079 (13)
C20	0.0234 (12)	0.0349 (14)	0.0321 (14)	−0.0103 (11)	0.0003 (10)	−0.0062 (11)
C21	0.0351 (16)	0.0365 (17)	0.079 (3)	−0.0153 (14)	−0.0067 (16)	−0.0175 (17)
C22	0.0331 (15)	0.064 (2)	0.0496 (19)	−0.0235 (15)	0.0041 (14)	−0.0259 (17)
C23	0.0314 (15)	0.0464 (18)	0.056 (2)	−0.0190 (14)	−0.0093 (14)	0.0010 (15)
C24	0.0276 (14)	0.0388 (17)	0.078 (3)	−0.0059 (13)	−0.0101 (15)	−0.0242 (17)
C25	0.0315 (15)	0.089 (3)	0.047 (2)	−0.0249 (18)	0.0012 (14)	−0.031 (2)
C26	0.0394 (17)	0.059 (2)	0.058 (2)	−0.0292 (17)	−0.0142 (16)	0.0092 (17)

Geometric parameters (Å, º) top

Pd1—Cl2	2.2635 (7)	C11—C12	1.386 (5)
Pd1—Cl1	2.2929 (7)	C11—H11	0.9500
Pd1—Cl3ⁱ	2.3292 (7)	C12—C13	1.374 (5)
Pd1—Cl3	2.3374 (7)	C12—H12	0.9500
Pd1—Pd1ⁱ	3.4060 (4)	C13—C14	1.381 (4)
Cl3—Pd1ⁱ	2.3292 (7)	C13—H13	0.9500
N1—C1	1.343 (3)	C14—H14	0.9500
N1—C9	1.426 (3)	C15—C16	1.383 (3)
N1—C8	1.481 (3)	C15—C20	1.388 (3)
N2—C1	1.327 (3)	C16—C17	1.386 (4)
N2—C15	1.424 (3)	C16—H16	0.9500
N2—H2	0.8800	C17—C18	1.380 (4)
C1—C2	1.456 (4)	C17—H17	0.9500
C2—C3	1.388 (4)	C18—C19	1.382 (4)
C2—C7	1.391 (4)	C18—H18	0.9500
C3—C4	1.381 (4)	C19—C20	1.390 (4)
C3—H3	0.9500	C19—H19	0.9500
C4—C5	1.397 (5)	C20—H20	0.9500
C4—H4	0.9500	C21—C22	1.367 (5)
C5—C6	1.381 (5)	C21—C26	1.369 (5)
C5—H5	0.9500	C21—H21	0.9500
C6—C7	1.391 (4)	C22—C23	1.374 (5)
C6—H6	0.9500	C22—H22	0.9500
C7—C8	1.490 (4)	C23—C24	1.377 (5)
C8—H8A	0.9900	C23—H23	0.9500
C8—H8B	0.9900	C24—C25	1.371 (5)
C9—C10	1.385 (4)	C24—H24	0.9500
C9—C14	1.392 (4)	C25—C26	1.393 (5)
C10—C11	1.386 (4)	C25—H25	0.9500
C10—H10	0.9500	C26—H26	0.9500

Cl2—Pd1—Cl1	91.32 (3)	C11—C10—H10	120.3
Cl2—Pd1—Cl3ⁱ	91.00 (3)	C10—C11—C12	119.8 (3)
Cl1—Pd1—Cl3ⁱ	177.33 (3)	C10—C11—H11	120.1
Cl2—Pd1—Cl3	176.86 (3)	C12—C11—H11	120.1
Cl1—Pd1—Cl3	91.47 (3)	C13—C12—C11	120.9 (3)
Cl3ⁱ—Pd1—Cl3	86.25 (3)	C13—C12—H12	119.6
Cl2—Pd1—Pd1ⁱ	134.20 (2)	C11—C12—H12	119.6
Cl1—Pd1—Pd1ⁱ	134.48 (2)	C12—C13—C14	119.8 (3)
Cl3ⁱ—Pd1—Pd1ⁱ	43.218 (17)	C12—C13—H13	120.1
Cl3—Pd1—Pd1ⁱ	43.030 (18)	C14—C13—H13	120.1
Pd1ⁱ—Cl3—Pd1	93.75 (3)	C13—C14—C9	119.6 (3)
C1—N1—C9	128.5 (2)	C13—C14—H14	120.2
C1—N1—C8	111.3 (2)	C9—C14—H14	120.2
C9—N1—C8	119.7 (2)	C16—C15—C20	121.3 (2)
C1—N2—C15	127.3 (2)	C16—C15—N2	119.6 (2)
C1—N2—H2	116.3	C20—C15—N2	119.0 (2)
C15—N2—H2	116.4	C15—C16—C17	119.0 (2)
N2—C1—N1	126.8 (2)	C15—C16—H16	120.5
N2—C1—C2	124.2 (2)	C17—C16—H16	120.5
N1—C1—C2	108.9 (2)	C18—C17—C16	120.5 (3)
C3—C2—C7	122.0 (3)	C18—C17—H17	119.8
C3—C2—C1	130.0 (3)	C16—C17—H17	119.8
C7—C2—C1	107.7 (2)	C17—C18—C19	120.1 (3)
C4—C3—C2	117.3 (3)	C17—C18—H18	120.0
C4—C3—H3	121.3	C19—C18—H18	120.0
C2—C3—H3	121.3	C18—C19—C20	120.4 (3)
C3—C4—C5	120.9 (3)	C18—C19—H19	119.8
C3—C4—H4	119.5	C20—C19—H19	119.8
C5—C4—H4	119.5	C15—C20—C19	118.7 (3)
C6—C5—C4	121.7 (3)	C15—C20—H20	120.6
C6—C5—H5	119.2	C19—C20—H20	120.6
C4—C5—H5	119.2	C22—C21—C26	120.6 (3)
C5—C6—C7	117.7 (3)	C22—C21—H21	119.7
C5—C6—H6	121.2	C26—C21—H21	119.7
C7—C6—H6	121.2	C21—C22—C23	120.4 (3)
C2—C7—C6	120.4 (3)	C21—C22—H22	119.8
C2—C7—C8	109.5 (2)	C23—C22—H22	119.8
C6—C7—C8	130.0 (3)	C22—C23—C24	119.6 (3)
N1—C8—C7	102.4 (2)	C22—C23—H23	120.2
N1—C8—H8A	111.3	C24—C23—H23	120.2
C7—C8—H8A	111.3	C25—C24—C23	120.3 (3)
N1—C8—H8B	111.3	C25—C24—H24	119.9
C7—C8—H8B	111.3	C23—C24—H24	119.9
H8A—C8—H8B	109.2	C24—C25—C26	119.9 (3)
C10—C9—C14	120.6 (3)	C24—C25—H25	120.0
C10—C9—N1	120.8 (2)	C26—C25—H25	120.0
C14—C9—N1	118.6 (2)	C21—C26—C25	119.2 (3)
C9—C10—C11	119.3 (3)	C21—C26—H26	120.4
C9—C10—H10	120.3	C25—C26—H26	120.4

Cl1—Pd1—Cl3—Pd1ⁱ	−178.61 (3)	C8—N1—C9—C10	−133.0 (3)
Cl3ⁱ—Pd1—Cl3—Pd1ⁱ	0.0	C1—N1—C9—C14	−144.4 (3)
C15—N2—C1—N1	21.0 (4)	C8—N1—C9—C14	44.9 (3)
C15—N2—C1—C2	−155.2 (2)	C14—C9—C10—C11	2.1 (4)
C9—N1—C1—N2	15.2 (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—C2	3.1 (3)	C11—C12—C13—C14	2.0 (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—C7	173.0 (2)	N1—C9—C14—C13	−178.9 (2)
N1—C1—C2—C7	−3.8 (3)	C1—N2—C15—C16	42.8 (4)
C7—C2—C3—C4	−1.3 (4)	C1—N2—C15—C20	−139.8 (3)
C1—C2—C3—C4	172.4 (3)	C20—C15—C16—C17	1.7 (4)
C2—C3—C4—C5	0.1 (5)	N2—C15—C16—C17	179.1 (2)
C3—C4—C5—C6	0.9 (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—C6	1.6 (4)	C17—C18—C19—C20	0.6 (5)
C1—C2—C7—C6	−173.4 (3)	C16—C15—C20—C19	−1.8 (4)
C3—C2—C7—C8	177.9 (3)	N2—C15—C20—C19	−179.2 (2)
C1—C2—C7—C8	3.0 (3)	C18—C19—C20—C15	0.6 (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—C24	0.1 (5)
C1—N1—C8—C7	−1.3 (3)	C22—C23—C24—C25	0.1 (5)
C9—N1—C8—C7	170.9 (2)	C23—C24—C25—C26	−0.1 (5)
C2—C7—C8—N1	−1.1 (3)	C22—C21—C26—C25	0.3 (5)
C6—C7—C8—N1	174.7 (3)	C24—C25—C26—C21	−0.1 (5)
C1—N1—C9—C10	37.6 (4)

Symmetry code: (i) −x, −y+2, −z.

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N2—H2···Cl1	0.88	2.37	3.242 (2)	171

Experimental details

Crystal data
Chemical formula	(C₂₀H₁₇N₂)₂[Pd₂Cl₆]·2C₆H₆
M_r	1152.46
Crystal system, space group	Triclinic, P1
Temperature (K)	173
a, b, c (Å)	9.5457 (3), 9.9754 (3), 14.8002 (5)
α, β, γ (°)	74.270 (2), 80.615 (2), 63.228 (2)
V (Å³)	1209.74 (7)
Z	1
Radiation type	Mo Kα
µ (mm⁻¹)	1.12
Crystal size (mm)	0.22 × 0.18 × 0.05

Data collection
Diffractometer	Bruker–Nonius KappaCCD diffractometer
Absorption correction	ψ scan (SHELXTL; Sheldrick, 2008)
T_min, T_max	0.791, 0.946
No. of measured, independent and observed [I > 2σ(I)] reflections	18458, 6458, 5322
R_int	0.038
(sin θ/λ)_max (Å⁻¹)	0.685

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.039, 0.094, 1.04
No. of reflections	6458
No. of parameters	290
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.82, −0.94

Computer programs: COLLECT (Nonius, 1998), SCALEPACK (Otwinowski & Minor, 1997), DENZO and SCALEPACK (Otwinowski & Minor 1997), SIR97 (Altomare et al., 1999), SHELXL97 (Sheldrick, 2008), ORTEP-3 for Windows (Farrugia, 1997).

Selected geometric parameters (Å, º) top

Pd1—Cl2	2.2635 (7)	Pd1—Cl3ⁱ	2.3292 (7)
Pd1—Cl1	2.2929 (7)	Pd1—Cl3	2.3374 (7)

Cl2—Pd1—Cl1	91.32 (3)	Cl2—Pd1—Cl3	176.86 (3)
Cl2—Pd1—Cl3ⁱ	91.00 (3)	Cl1—Pd1—Cl3	91.47 (3)
Cl1—Pd1—Cl3ⁱ	177.33 (3)	Cl3ⁱ—Pd1—Cl3	86.25 (3)

Symmetry code: (i) −x, −y+2, −z.

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N2—H2···Cl1	0.88	2.37	3.242 (2)	170.8

Acknowledgements

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.

References

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. Web of Science CrossRef CAS IUCr Journals Google Scholar
Bartczak, T. J., Michalska, Z. M., Ostaszewski, B., Sobota, P. & Strzelec, K. (2001). Inorg. Chim. Acta, 319, 229–234. Web of Science CSD CrossRef CAS Google Scholar
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Volume 64| Part 7| July 2008| Pages m907-m908

doi:10.1107/S1600536808017005

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

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

Related literature

Experimental

Crystal data

Data collection

Refinement

Supporting information

Acknowledgements

References

metal-organic compounds

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