trans-Diiodidobis(2-phenyl-pyridine-κN)palladium(II).

In the title complex, [PdI(2)(C(11)H(9)N)(2)], the Pd(II) ion has a distorted trans-I(2)N(2) square-planar coordination geometry defined by two N atoms from two 2-phenyl-pyridine ligands and two I(-) anions. The 2-phenyl-pyridine ligands are not planar, the dihedral angles between the pyridine and benzene rings being 50.1 (2) and 45.7 (2)°. An inter-molecular π-π inter-action between the six-membered rings is present, the ring centroid-centroid distance being 3.898 (4) Å.

Related literature

For a related structure, [PdCl2(C11H9N)2], see: Ha (2011 ▶).

Experimental

Crystal data

[PdI2(C11H9N)2]

M = 670.58

Monoclinic,

a = 9.9163 (10) Å

b = 14.4759 (14) Å

c = 14.9917 (15) Å

β = 103.663 (2)°

V = 2091.1 (4) Å3

Z = 4

Mo Kα radiation

μ = 3.85 mm−1

T = 200 K

0.25 × 0.23 × 0.11 mm

Data collection

Bruker SMART 1000 CCD diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2000 ▶) T min = 0.511, T max = 0.655

15087 measured reflections

5163 independent reflections

2650 reflections with I > 2σ(I)

R int = 0.061

Refinement

R[F 2 > 2σ(F 2)] = 0.041

wR(F 2) = 0.110

S = 0.98

5163 reflections

244 parameters

H-atom parameters constrained

Δρmax = 2.20 e Å−3

Δρmin = −1.15 e Å−3

Data collection: SMART (Bruker, 2000 ▶); cell refinement: SAINT (Bruker, 2000 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: ORTEP-3 (Farrugia, 1997 ▶) and PLATON (Spek, 2009 ▶); software used to prepare material for publication: SHELXL97.

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S1600536811055425/is5038sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536811055425/is5038Isup2.hkl

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

[PdI2(C11H9N)2]	F(000) = 1264
Mr = 670.58	Dx = 2.130 Mg m−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 3071 reflections
a = 9.9163 (10) Å	θ = 2.5–27.7°
b = 14.4759 (14) Å	µ = 3.85 mm−1
c = 14.9917 (15) Å	T = 200 K
β = 103.663 (2)°	Plate, red
V = 2091.1 (4) Å3	0.25 × 0.23 × 0.11 mm
Z = 4

Bruker SMART 1000 CCD diffractometer	5163 independent reflections
Radiation source: fine-focus sealed tube	2650 reflections with I > 2σ(I)
graphite	Rint = 0.061
φ and ω scans	θmax = 28.3°, θmin = 2.0°
Absorption correction: multi-scan (SADABS; Bruker, 2000)	h = −12→13
Tmin = 0.511, Tmax = 0.655	k = −18→19
15087 measured reflections	l = −19→17

Refinement on F2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.041	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.110	H-atom parameters constrained
S = 0.98	w = 1/[σ2(Fo2) + (0.0329P)2] where P = (Fo2 + 2Fc2)/3
5163 reflections	(Δ/σ)max < 0.001
244 parameters	Δρmax = 2.20 e Å−3
0 restraints	Δρmin = −1.15 e Å−3

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.

	x	y	z	Uiso*/Ueq
Pd1	0.75033 (5)	0.14770 (3)	0.24074 (3)	0.02261 (13)
I1	0.61261 (5)	0.14579 (3)	0.36973 (3)	0.03177 (14)
I2	0.88936 (5)	0.15018 (3)	0.11195 (3)	0.03134 (14)
N1	0.6117 (5)	0.0560 (3)	0.1689 (3)	0.0223 (12)
N2	0.8874 (6)	0.2392 (4)	0.3151 (4)	0.0294 (14)
C1	0.6530 (7)	−0.0331 (4)	0.1743 (4)	0.0282 (16)
H1	0.7465	−0.0464	0.2043	0.034*
C2	0.5691 (8)	−0.1047 (5)	0.1396 (5)	0.0365 (19)
H2	0.6031	−0.1663	0.1452	0.044*
C3	0.4332 (8)	−0.0863 (5)	0.0959 (5)	0.0339 (18)
H3	0.3708	−0.1349	0.0720	0.041*
C4	0.3903 (7)	0.0041 (5)	0.0877 (5)	0.0325 (18)
H4	0.2980	0.0181	0.0556	0.039*
C5	0.4787 (7)	0.0753 (4)	0.1254 (4)	0.0249 (16)
C6	0.4288 (7)	0.1721 (4)	0.1201 (4)	0.0252 (16)
C7	0.3044 (7)	0.1915 (5)	0.1446 (4)	0.0281 (16)
H7	0.2540	0.1430	0.1645	0.034*
C8	0.2542 (8)	0.2810 (5)	0.1401 (5)	0.0382 (19)
H8	0.1710	0.2940	0.1587	0.046*
C9	0.3244 (8)	0.3508 (5)	0.1090 (5)	0.0354 (18)
H9	0.2890	0.4120	0.1056	0.043*
C10	0.4459 (7)	0.3331 (5)	0.0824 (5)	0.0319 (18)
H10	0.4938	0.3821	0.0610	0.038*
C11	0.4991 (7)	0.2430 (5)	0.0868 (4)	0.0299 (17)
H11	0.5818	0.2303	0.0674	0.036*
C12	0.8459 (8)	0.3265 (5)	0.3126 (5)	0.0348 (19)
H12	0.7536	0.3406	0.2805	0.042*
C13	0.9289 (8)	0.3975 (5)	0.3540 (5)	0.043 (2)
H13	0.8956	0.4592	0.3496	0.052*
C14	1.0588 (8)	0.3775 (5)	0.4010 (5)	0.040 (2)
H14	1.1177	0.4255	0.4310	0.048*
C15	1.1072 (8)	0.2880 (5)	0.4060 (5)	0.042 (2)
H15	1.1990	0.2742	0.4393	0.051*
C16	1.0189 (8)	0.2168 (5)	0.3612 (5)	0.0321 (18)
C17	1.0712 (8)	0.1208 (5)	0.3653 (5)	0.0351 (19)
C18	1.2040 (8)	0.1041 (6)	0.3535 (5)	0.041 (2)
H18	1.2584	0.1540	0.3402	0.049*
C19	1.2577 (8)	0.0150 (5)	0.3609 (5)	0.044 (2)
H19	1.3474	0.0041	0.3508	0.053*
C20	1.1810 (9)	−0.0581 (6)	0.3831 (5)	0.049 (2)
H20	1.2183	−0.1189	0.3893	0.059*
C21	1.0499 (8)	−0.0414 (5)	0.3962 (5)	0.044 (2)
H21	0.9967	−0.0909	0.4116	0.053*
C22	0.9956 (8)	0.0471 (5)	0.3871 (5)	0.041 (2)
H22	0.9050	0.0576	0.3958	0.049*

	U11	U22	U33	U12	U13	U23
Pd1	0.0173 (3)	0.0242 (3)	0.0258 (3)	−0.0034 (2)	0.0040 (2)	−0.0018 (2)
I1	0.0291 (3)	0.0354 (3)	0.0328 (3)	−0.0015 (2)	0.0115 (2)	−0.0018 (2)
I2	0.0253 (3)	0.0370 (3)	0.0331 (3)	−0.0029 (2)	0.0095 (2)	−0.0013 (2)
N1	0.017 (3)	0.027 (3)	0.021 (3)	−0.005 (2)	0.001 (2)	0.001 (2)
N2	0.026 (4)	0.031 (3)	0.029 (3)	−0.011 (3)	0.002 (3)	−0.001 (3)
C1	0.029 (4)	0.024 (4)	0.032 (4)	0.002 (3)	0.009 (3)	−0.003 (3)
C2	0.045 (5)	0.021 (4)	0.044 (5)	−0.001 (3)	0.011 (4)	−0.005 (3)
C3	0.030 (5)	0.038 (4)	0.032 (4)	−0.013 (4)	0.003 (3)	−0.002 (3)
C4	0.030 (5)	0.041 (5)	0.024 (4)	0.002 (4)	0.001 (3)	0.009 (3)
C5	0.031 (4)	0.025 (4)	0.016 (3)	−0.004 (3)	0.002 (3)	−0.002 (3)
C6	0.018 (4)	0.030 (4)	0.025 (4)	0.002 (3)	0.001 (3)	0.005 (3)
C7	0.026 (4)	0.036 (4)	0.026 (4)	−0.006 (3)	0.014 (3)	0.001 (3)
C8	0.023 (5)	0.046 (5)	0.046 (5)	0.012 (4)	0.010 (3)	0.003 (4)
C9	0.037 (5)	0.026 (4)	0.042 (4)	0.003 (4)	0.007 (3)	0.004 (4)
C10	0.030 (5)	0.034 (4)	0.034 (4)	−0.005 (3)	0.011 (3)	−0.001 (3)
C11	0.020 (4)	0.038 (4)	0.029 (4)	0.003 (3)	0.002 (3)	0.000 (3)
C12	0.046 (5)	0.024 (4)	0.035 (4)	−0.003 (3)	0.011 (4)	−0.002 (3)
C13	0.044 (6)	0.034 (5)	0.053 (5)	−0.010 (4)	0.014 (4)	−0.002 (4)
C14	0.039 (5)	0.036 (5)	0.043 (5)	−0.010 (4)	0.005 (4)	−0.018 (4)
C15	0.039 (5)	0.050 (5)	0.034 (4)	−0.012 (4)	−0.001 (4)	−0.002 (4)
C16	0.036 (5)	0.033 (4)	0.028 (4)	−0.010 (3)	0.010 (3)	0.006 (3)
C17	0.028 (5)	0.045 (5)	0.028 (4)	−0.003 (4)	0.000 (3)	0.002 (3)
C18	0.023 (5)	0.054 (5)	0.042 (5)	−0.005 (4)	0.000 (4)	0.005 (4)
C19	0.032 (5)	0.046 (5)	0.053 (5)	0.004 (4)	0.008 (4)	0.003 (4)
C20	0.047 (6)	0.047 (5)	0.047 (5)	0.008 (4)	−0.002 (4)	0.001 (4)
C21	0.036 (5)	0.036 (5)	0.059 (5)	−0.001 (4)	0.012 (4)	0.012 (4)
C22	0.024 (5)	0.050 (5)	0.044 (5)	−0.002 (4)	0.001 (3)	0.007 (4)

Pd1—N1	2.027 (5)	C9—H9	0.9500
Pd1—N2	2.031 (5)	C10—C11	1.402 (9)
Pd1—I1	2.6178 (8)	C10—H10	0.9500
Pd1—I2	2.6244 (8)	C11—H11	0.9500
N1—C1	1.350 (8)	C12—C13	1.369 (9)
N1—C5	1.356 (8)	C12—H12	0.9500
N2—C12	1.328 (8)	C13—C14	1.346 (9)
N2—C16	1.363 (8)	C13—H13	0.9500
C1—C2	1.354 (9)	C14—C15	1.378 (10)
C1—H1	0.9500	C14—H14	0.9500
C2—C3	1.378 (9)	C15—C16	1.415 (9)
C2—H2	0.9500	C15—H15	0.9500
C3—C4	1.372 (9)	C16—C17	1.481 (10)
C3—H3	0.9500	C17—C22	1.386 (10)
C4—C5	1.384 (8)	C17—C18	1.390 (10)
C4—H4	0.9500	C18—C19	1.389 (10)
C5—C6	1.482 (9)	C18—H18	0.9500
C6—C11	1.397 (9)	C19—C20	1.389 (10)
C6—C7	1.397 (9)	C19—H19	0.9500
C7—C8	1.384 (9)	C20—C21	1.381 (11)
C7—H7	0.9500	C20—H20	0.9500
C8—C9	1.370 (10)	C21—C22	1.385 (10)
C8—H8	0.9500	C21—H21	0.9500
C9—C10	1.380 (10)	C22—H22	0.9500
N1—Pd1—N2	178.8 (2)	C9—C10—C11	120.2 (7)
N1—Pd1—I1	88.78 (15)	C9—C10—H10	119.9
N2—Pd1—I1	89.99 (17)	C11—C10—H10	119.9
N1—Pd1—I2	91.51 (15)	C6—C11—C10	119.1 (7)
N2—Pd1—I2	89.71 (17)	C6—C11—H11	120.5
I1—Pd1—I2	179.71 (3)	C10—C11—H11	120.5
C1—N1—C5	118.2 (5)	N2—C12—C13	123.6 (7)
C1—N1—Pd1	115.8 (4)	N2—C12—H12	118.2
C5—N1—Pd1	125.6 (4)	C13—C12—H12	118.2
C12—N2—C16	119.5 (6)	C14—C13—C12	118.3 (7)
C12—N2—Pd1	116.3 (5)	C14—C13—H13	120.8
C16—N2—Pd1	124.0 (5)	C12—C13—H13	120.8
N1—C1—C2	124.0 (6)	C13—C14—C15	120.6 (7)
N1—C1—H1	118.0	C13—C14—H14	119.7
C2—C1—H1	118.0	C15—C14—H14	119.7
C1—C2—C3	118.5 (7)	C14—C15—C16	119.3 (7)
C1—C2—H2	120.7	C14—C15—H15	120.3
C3—C2—H2	120.7	C16—C15—H15	120.3
C4—C3—C2	118.4 (6)	N2—C16—C15	118.6 (7)
C4—C3—H3	120.8	N2—C16—C17	121.9 (6)
C2—C3—H3	120.8	C15—C16—C17	119.5 (7)
C3—C4—C5	121.4 (6)	C22—C17—C18	118.6 (7)
C3—C4—H4	119.3	C22—C17—C16	121.9 (7)
C5—C4—H4	119.3	C18—C17—C16	119.4 (7)
N1—C5—C4	119.6 (6)	C19—C18—C17	120.5 (8)
N1—C5—C6	119.7 (5)	C19—C18—H18	119.8
C4—C5—C6	120.7 (6)	C17—C18—H18	119.8
C11—C6—C7	119.5 (6)	C20—C19—C18	120.3 (8)
C11—C6—C5	121.7 (7)	C20—C19—H19	119.8
C7—C6—C5	118.7 (6)	C18—C19—H19	119.8
C8—C7—C6	120.3 (7)	C21—C20—C19	119.2 (8)
C8—C7—H7	119.8	C21—C20—H20	120.4
C6—C7—H7	119.8	C19—C20—H20	120.4
C9—C8—C7	120.1 (7)	C20—C21—C22	120.4 (8)
C9—C8—H8	119.9	C20—C21—H21	119.8
C7—C8—H8	119.9	C22—C21—H21	119.8
C8—C9—C10	120.6 (7)	C21—C22—C17	121.0 (8)
C8—C9—H9	119.7	C21—C22—H22	119.5
C10—C9—H9	119.7	C17—C22—H22	119.5
I1—Pd1—N1—C1	−100.1 (5)	C8—C9—C10—C11	0.1 (11)
I2—Pd1—N1—C1	79.8 (5)	C7—C6—C11—C10	2.6 (9)
I1—Pd1—N1—C5	72.3 (5)	C5—C6—C11—C10	179.2 (6)
I2—Pd1—N1—C5	−107.7 (5)	C9—C10—C11—C6	−1.2 (10)
I1—Pd1—N2—C12	−78.3 (5)	C16—N2—C12—C13	0.5 (11)
I2—Pd1—N2—C12	101.7 (5)	Pd1—N2—C12—C13	−175.6 (6)
I1—Pd1—N2—C16	105.8 (6)	N2—C12—C13—C14	−1.2 (12)
I2—Pd1—N2—C16	−74.2 (6)	C12—C13—C14—C15	0.9 (12)
C5—N1—C1—C2	−0.7 (10)	C13—C14—C15—C16	0.0 (12)
Pd1—N1—C1—C2	172.3 (6)	C12—N2—C16—C15	0.5 (10)
N1—C1—C2—C3	0.1 (11)	Pd1—N2—C16—C15	176.3 (5)
C1—C2—C3—C4	1.5 (11)	C12—N2—C16—C17	−179.3 (7)
C2—C3—C4—C5	−2.6 (11)	Pd1—N2—C16—C17	−3.5 (10)
C1—N1—C5—C4	−0.3 (9)	C14—C15—C16—N2	−0.7 (11)
Pd1—N1—C5—C4	−172.6 (5)	C14—C15—C16—C17	179.1 (7)
C1—N1—C5—C6	178.5 (6)	N2—C16—C17—C22	−47.9 (10)
Pd1—N1—C5—C6	6.3 (9)	C15—C16—C17—C22	132.3 (8)
C3—C4—C5—N1	2.0 (11)	N2—C16—C17—C18	136.7 (7)
C3—C4—C5—C6	−176.9 (7)	C15—C16—C17—C18	−43.1 (10)
N1—C5—C6—C11	52.8 (9)	C22—C17—C18—C19	1.7 (11)
C4—C5—C6—C11	−128.4 (7)	C16—C17—C18—C19	177.3 (7)
N1—C5—C6—C7	−130.6 (7)	C17—C18—C19—C20	−2.0 (12)
C4—C5—C6—C7	48.2 (9)	C18—C19—C20—C21	1.1 (12)
C11—C6—C7—C8	−3.0 (10)	C19—C20—C21—C22	0.1 (12)
C5—C6—C7—C8	−179.7 (6)	C20—C21—C22—C17	−0.5 (12)
C6—C7—C8—C9	1.9 (11)	C18—C17—C22—C21	−0.5 (11)
C7—C8—C9—C10	−0.5 (11)	C16—C17—C22—C21	−175.9 (7)

Table 1

Selected bond lengths (Å)

Pd1—N1	2.027 (5)
Pd1—N2	2.031 (5)
Pd1—I1	2.6178 (8)
Pd1—I2	2.6244 (8)