(2,3-Di-2-pyridyl-pyrazine-κN,N)diiodidopalladium(II).

The Pd(II) ion in the title complex, [PdI(2)(C(14)H(10)N(4))], is four-coordinated in a slightly distorted square-planar environment by the two pyridine N atoms of the chelating 2,3-di-2-pyridyl-pyrazine (dpp) ligand and two iodide anions. In the crystal, the pyridine rings are considerably inclined to the least-squares plane of the PdI(2)N(2) unit [maximum deviation = 0.090 (2) Å], making dihedral angles of 65.0 (2) and 66.6 (2)°. The pyrazine ring is perpendicular to the unit plane, with a dihedral angle of 89.9 (2)°. The complex mol-ecules are connected by C-H⋯I hydrogen bonds, forming a helical chain along the b axis.

Related literature

For the crystal structure of the yellow form of [PtBr2(dpp)] which is isotypic to the title complex, see: Ha (2011 ▶).

Experimental

Crystal data

[PdI2(C14H10N4)]

M = 594.46

Monoclinic,

a = 8.7936 (12) Å

b = 15.528 (2) Å

c = 12.3351 (17) Å

β = 102.118 (3)°

V = 1646.8 (4) Å3

Z = 4

Mo Kα radiation

μ = 4.87 mm−1

T = 200 K

0.42 × 0.31 × 0.29 mm

Data collection

Bruker SMART 1000 CCD diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2000 ▶) T min = 0.183, T max = 0.243

10659 measured reflections

3513 independent reflections

2968 reflections with I > 2σ(I)

R int = 0.022

Refinement

R[F 2 > 2σ(F 2)] = 0.035

wR(F 2) = 0.103

S = 1.05

3513 reflections

190 parameters

H-atom parameters constrained

Δρmax = 1.28 e Å−3

Δρmin = −1.42 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/S1600536811044023/is2795sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536811044023/is2795Isup2.hkl

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

[PdI2(C14H10N4)]	F(000) = 1096
Mr = 594.46	Dx = 2.398 Mg m−3
Monoclinic, P21/n	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2yn	Cell parameters from 7148 reflections
a = 8.7936 (12) Å	θ = 2.4–27.0°
b = 15.528 (2) Å	µ = 4.87 mm−1
c = 12.3351 (17) Å	T = 200 K
β = 102.118 (3)°	Block, red-brown
V = 1646.8 (4) Å3	0.42 × 0.31 × 0.29 mm
Z = 4

Bruker SMART 1000 CCD diffractometer	3513 independent reflections
Radiation source: fine-focus sealed tube	2968 reflections with I > 2σ(I)
graphite	Rint = 0.022
φ and ω scans	θmax = 27.0°, θmin = 2.1°
Absorption correction: multi-scan (SADABS; Bruker, 2000)	h = −11→10
Tmin = 0.183, Tmax = 0.243	k = −19→19
10659 measured reflections	l = −11→15

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)] = 0.035	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.103	H-atom parameters constrained
S = 1.05	w = 1/[σ2(Fo2) + (0.0477P)2 + 7.4036P] where P = (Fo2 + 2Fc2)/3
3513 reflections	(Δ/σ)max = 0.001
190 parameters	Δρmax = 1.28 e Å−3
0 restraints	Δρmin = −1.42 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	0.46673 (5)	0.06358 (3)	0.67952 (3)	0.03147 (13)
I1	0.61860 (5)	−0.07875 (3)	0.68473 (4)	0.04827 (15)
I2	0.71972 (6)	0.15314 (3)	0.73389 (4)	0.05207 (16)
N1	0.1852 (6)	0.0054 (3)	0.9114 (4)	0.0419 (12)
N2	0.2351 (7)	0.1813 (4)	0.9159 (5)	0.0473 (13)
N3	0.2628 (5)	−0.0048 (3)	0.6446 (4)	0.0314 (10)
N4	0.3330 (6)	0.1733 (3)	0.6587 (4)	0.0375 (11)
C1	0.2007 (6)	0.0473 (4)	0.8187 (5)	0.0332 (12)
C2	0.2265 (7)	0.1360 (4)	0.8211 (5)	0.0347 (12)
C3	0.2229 (9)	0.1385 (5)	1.0064 (6)	0.0516 (17)
H3	0.2304	0.1690	1.0740	0.062*
C4	0.1993 (9)	0.0498 (4)	1.0047 (6)	0.0495 (16)
H4	0.1932	0.0207	1.0714	0.059*
C5	0.1683 (6)	−0.0075 (3)	0.7174 (5)	0.0309 (11)
C6	0.0425 (7)	−0.0623 (4)	0.7030 (6)	0.0430 (15)
H6	−0.0216	−0.0642	0.7561	0.052*
C7	0.0103 (7)	−0.1154 (4)	0.6092 (6)	0.0485 (16)
H7	−0.0753	−0.1541	0.5981	0.058*
C8	0.1045 (7)	−0.1106 (4)	0.5334 (5)	0.0418 (14)
H8	0.0844	−0.1452	0.4684	0.050*
C9	0.2272 (7)	−0.0552 (4)	0.5534 (5)	0.0385 (13)
H9	0.2913	−0.0517	0.5004	0.046*
C10	0.2329 (7)	0.1913 (4)	0.7239 (5)	0.0374 (13)
C11	0.1398 (8)	0.2639 (4)	0.7055 (6)	0.0470 (16)
H11	0.0711	0.2768	0.7533	0.056*
C12	0.1467 (10)	0.3171 (4)	0.6187 (6)	0.0558 (19)
H12	0.0820	0.3665	0.6050	0.067*
C13	0.2478 (10)	0.2984 (4)	0.5515 (6)	0.0554 (19)
H13	0.2543	0.3348	0.4907	0.067*
C14	0.3406 (9)	0.2259 (4)	0.5733 (5)	0.0497 (16)
H14	0.4113	0.2130	0.5270	0.060*

	U11	U22	U33	U12	U13	U23
Pd1	0.0364 (2)	0.0300 (2)	0.0295 (2)	−0.00616 (17)	0.01056 (17)	−0.00251 (16)
I1	0.0419 (3)	0.0503 (3)	0.0548 (3)	0.00162 (18)	0.01512 (19)	0.00031 (19)
I2	0.0562 (3)	0.0592 (3)	0.0431 (3)	−0.0268 (2)	0.0154 (2)	−0.0105 (2)
N1	0.053 (3)	0.037 (3)	0.036 (3)	−0.003 (2)	0.013 (2)	−0.002 (2)
N2	0.062 (4)	0.039 (3)	0.041 (3)	0.002 (3)	0.012 (3)	−0.011 (2)
N3	0.034 (2)	0.026 (2)	0.034 (2)	−0.0009 (18)	0.0070 (19)	0.0001 (19)
N4	0.054 (3)	0.027 (2)	0.031 (2)	−0.004 (2)	0.007 (2)	−0.0016 (19)
C1	0.032 (3)	0.034 (3)	0.034 (3)	0.001 (2)	0.007 (2)	−0.006 (2)
C2	0.038 (3)	0.030 (3)	0.037 (3)	−0.001 (2)	0.010 (2)	−0.004 (2)
C3	0.072 (5)	0.048 (4)	0.038 (4)	−0.002 (3)	0.018 (3)	−0.009 (3)
C4	0.068 (5)	0.044 (4)	0.040 (4)	−0.001 (3)	0.019 (3)	−0.004 (3)
C5	0.034 (3)	0.026 (3)	0.034 (3)	0.001 (2)	0.010 (2)	−0.003 (2)
C6	0.034 (3)	0.055 (4)	0.044 (4)	−0.009 (3)	0.017 (3)	−0.009 (3)
C7	0.037 (3)	0.046 (4)	0.062 (4)	−0.012 (3)	0.008 (3)	−0.014 (3)
C8	0.047 (4)	0.038 (3)	0.039 (3)	−0.005 (3)	0.004 (3)	−0.014 (3)
C9	0.048 (3)	0.037 (3)	0.031 (3)	0.000 (3)	0.008 (2)	−0.007 (2)
C10	0.050 (3)	0.026 (3)	0.033 (3)	−0.004 (2)	−0.001 (3)	−0.003 (2)
C11	0.053 (4)	0.033 (3)	0.052 (4)	0.003 (3)	0.003 (3)	−0.004 (3)
C12	0.069 (5)	0.029 (3)	0.060 (4)	0.000 (3)	−0.008 (4)	0.004 (3)
C13	0.092 (6)	0.032 (3)	0.036 (3)	−0.007 (3)	0.001 (4)	0.004 (3)
C14	0.071 (5)	0.041 (3)	0.036 (3)	−0.011 (3)	0.008 (3)	−0.001 (3)

Pd1—N3	2.050 (5)	C4—H4	0.9500
Pd1—N4	2.056 (5)	C5—C6	1.378 (8)
Pd1—I1	2.5761 (7)	C6—C7	1.400 (9)
Pd1—I2	2.5898 (6)	C6—H6	0.9500
N1—C4	1.326 (8)	C7—C8	1.375 (10)
N1—C1	1.347 (8)	C7—H7	0.9500
N2—C3	1.321 (9)	C8—C9	1.362 (9)
N2—C2	1.353 (8)	C8—H8	0.9500
N3—C5	1.346 (7)	C9—H9	0.9500
N3—C9	1.352 (7)	C10—C11	1.384 (9)
N4—C10	1.340 (8)	C11—C12	1.363 (10)
N4—C14	1.346 (8)	C11—H11	0.9500
C1—C2	1.395 (8)	C12—C13	1.367 (12)
C1—C5	1.489 (7)	C12—H12	0.9500
C2—C10	1.486 (8)	C13—C14	1.383 (11)
C3—C4	1.393 (10)	C13—H13	0.9500
C3—H3	0.9500	C14—H14	0.9500
N3—Pd1—N4	87.17 (19)	C6—C5—C1	117.9 (5)
N3—Pd1—I1	89.26 (13)	C5—C6—C7	119.2 (6)
N4—Pd1—I1	173.87 (13)	C5—C6—H6	120.4
N3—Pd1—I2	176.70 (13)	C7—C6—H6	120.4
N4—Pd1—I2	91.43 (14)	C8—C7—C6	118.9 (6)
I1—Pd1—I2	92.38 (2)	C8—C7—H7	120.5
C4—N1—C1	118.5 (5)	C6—C7—H7	120.5
C3—N2—C2	118.0 (6)	C9—C8—C7	118.6 (6)
C5—N3—C9	118.0 (5)	C9—C8—H8	120.7
C5—N3—Pd1	120.7 (4)	C7—C8—H8	120.7
C9—N3—Pd1	120.9 (4)	N3—C9—C8	123.6 (6)
C10—N4—C14	119.3 (6)	N3—C9—H9	118.2
C10—N4—Pd1	121.9 (4)	C8—C9—H9	118.2
C14—N4—Pd1	118.7 (5)	N4—C10—C11	120.8 (6)
N1—C1—C2	120.3 (5)	N4—C10—C2	120.3 (5)
N1—C1—C5	113.6 (5)	C11—C10—C2	118.9 (6)
C2—C1—C5	125.7 (5)	C12—C11—C10	120.0 (7)
N2—C2—C1	120.7 (6)	C12—C11—H11	120.0
N2—C2—C10	113.1 (5)	C10—C11—H11	120.0
C1—C2—C10	126.0 (5)	C11—C12—C13	119.3 (7)
N2—C3—C4	121.5 (6)	C11—C12—H12	120.4
N2—C3—H3	119.2	C13—C12—H12	120.4
C4—C3—H3	119.2	C12—C13—C14	119.2 (7)
N1—C4—C3	120.9 (6)	C12—C13—H13	120.4
N1—C4—H4	119.5	C14—C13—H13	120.4
C3—C4—H4	119.5	N4—C14—C13	121.4 (7)
N3—C5—C6	121.6 (5)	N4—C14—H14	119.3
N3—C5—C1	120.4 (5)	C13—C14—H14	119.3
N4—Pd1—N3—C5	−70.8 (4)	N1—C1—C5—C6	42.3 (7)
I1—Pd1—N3—C5	114.2 (4)	C2—C1—C5—C6	−130.1 (7)
N4—Pd1—N3—C9	116.0 (4)	N3—C5—C6—C7	−1.3 (10)
I1—Pd1—N3—C9	−59.1 (4)	C1—C5—C6—C7	−179.2 (6)
N3—Pd1—N4—C10	62.2 (5)	C5—C6—C7—C8	−0.6 (11)
I2—Pd1—N4—C10	−114.8 (4)	C6—C7—C8—C9	1.0 (10)
N3—Pd1—N4—C14	−114.1 (5)	C5—N3—C9—C8	−2.4 (9)
I2—Pd1—N4—C14	68.9 (5)	Pd1—N3—C9—C8	171.0 (5)
C4—N1—C1—C2	−1.8 (9)	C7—C8—C9—N3	0.6 (10)
C4—N1—C1—C5	−174.7 (6)	C14—N4—C10—C11	−1.2 (9)
C3—N2—C2—C1	2.0 (10)	Pd1—N4—C10—C11	−177.5 (4)
C3—N2—C2—C10	176.8 (6)	C14—N4—C10—C2	−177.7 (5)
N1—C1—C2—N2	−0.6 (9)	Pd1—N4—C10—C2	6.0 (7)
C5—C1—C2—N2	171.4 (6)	N2—C2—C10—N4	129.4 (6)
N1—C1—C2—C10	−174.7 (6)	C1—C2—C10—N4	−56.1 (8)
C5—C1—C2—C10	−2.7 (10)	N2—C2—C10—C11	−47.2 (8)
C2—N2—C3—C4	−1.1 (11)	C1—C2—C10—C11	127.3 (7)
C1—N1—C4—C3	2.7 (10)	N4—C10—C11—C12	1.6 (10)
N2—C3—C4—N1	−1.3 (12)	C2—C10—C11—C12	178.1 (6)
C9—N3—C5—C6	2.8 (8)	C10—C11—C12—C13	−1.0 (10)
Pd1—N3—C5—C6	−170.7 (5)	C11—C12—C13—C14	0.1 (11)
C9—N3—C5—C1	−179.4 (5)	C10—N4—C14—C13	0.3 (9)
Pd1—N3—C5—C1	7.2 (7)	Pd1—N4—C14—C13	176.7 (5)
N1—C1—C5—N3	−135.7 (6)	C12—C13—C14—N4	0.3 (11)
C2—C1—C5—N3	51.9 (8)

D—H···A	D—H	H···A	D···A	D—H···A
C11—H11···I1i	0.95	2.99	3.776 (7)	141.

Table 1

Selected bond lengths (Å)

Pd1—N3	2.050 (5)
Pd1—N4	2.056 (5)
Pd1—I1	2.5761 (7)
Pd1—I2	2.5898 (6)

Table 2

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C11—H11⋯I1i	0.95	2.99	3.776 (7)	141

Symmetry code: (i) .