(2,2'-Bipyridine-κN,N')dibromido-palladium(II) dichloro-methane solvate.

In the title compound, [PdBr(2)(C(10)H(8)N(2))]·CH(2)Cl(2), the Pd(2+) ion is four-coordinated in a slightly distorted square-planar environment by two N atoms of the chelating 2,2'-bipyridine ligand and two bromide ions. The compound displays intra-molecular C-H⋯Br hydrogen bonds and pairs of complex mol-ecules are assembled by inter-molecular C-H⋯Br hydrogen bonds. These pairs are connected by additional C-H⋯Br hydrogen bonds, forming a layer structure extending parallel to (011). Inter-molecular π-π inter-actions between the pyridine rings of the ligand are also present, the shortest centroid-centroid distance being 4.090 (9) Å.

Related literature

For the crystal structures of [PdX 2(bipy)] (X = Cl or Br), see: Maekawa et al. (1991 ▶); Smeets et al. (1997 ▶). For the crystal structure of [PdCl2(bipy)]·CH2Cl2 which is isotypic to the title compound, see: Vicente et al. (1997 ▶); Kim et al. (2009a ▶). For related Pt(II, IV)-bipyridine complexes, see: Osborn & Rogers (1974 ▶); Hambley (1986 ▶); Sartori et al. (2005 ▶); Momeni et al. (2007 ▶); Kim et al. (2009b ▶).

Experimental

Crystal data

[PdBr2(C10H8N2)]·CH2Cl2

M = 507.33

Triclinic,

a = 8.9323 (10) Å

b = 9.3035 (10) Å

c = 10.0113 (11) Å

α = 72.882 (2)°

β = 67.292 (2)°

γ = 80.995 (2)°

V = 732.60 (14) Å3

Z = 2

Mo Kα radiation

μ = 7.07 mm−1

T = 200 K

0.22 × 0.15 × 0.11 mm

Data collection

Bruker SMART 1000 CCD diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2000 ▶) T min = 0.707, T max = 1.000

5486 measured reflections

3574 independent reflections

2195 reflections with I > 2σ(I)

R int = 0.038

Refinement

R[F 2 > 2σ(F 2)] = 0.068

wR(F 2) = 0.188

S = 1.14

3574 reflections

163 parameters

H-atom parameters constrained

Δρmax = 2.13 e Å−3

Δρmin = −3.43 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 datablocks global, I. DOI: 10.1107/S1600536809039701/wm2260sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809039701/wm2260Isup2.hkl

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

[PdBr2(C10H8N2)]·CH2Cl2	Z = 2
Mr = 507.33	F(000) = 480
Triclinic, P1	Dx = 2.300 Mg m−3
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 8.9323 (10) Å	Cell parameters from 1623 reflections
b = 9.3035 (10) Å	θ = 2.3–26.7°
c = 10.0113 (11) Å	µ = 7.07 mm−1
α = 72.882 (2)°	T = 200 K
β = 67.292 (2)°	Block, dark orange
γ = 80.995 (2)°	0.22 × 0.15 × 0.11 mm
V = 732.60 (14) Å3

Bruker SMART 1000 CCD diffractometer	3574 independent reflections
Radiation source: fine-focus sealed tube	2195 reflections with I > 2σ(I)
graphite	Rint = 0.038
φ and ω scans	θmax = 28.3°, θmin = 2.3°
Absorption correction: multi-scan (SADABS; Bruker, 2000)	h = −11→11
Tmin = 0.707, Tmax = 1.000	k = −12→12
5486 measured reflections	l = −13→10

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)] = 0.068	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.188	H-atom parameters constrained
S = 1.14	w = 1/[σ2(Fo2) + 21.2252P] where P = (Fo2 + 2Fc2)/3
3574 reflections	(Δ/σ)max < 0.001
163 parameters	Δρmax = 2.13 e Å−3
0 restraints	Δρmin = −3.43 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	0.17533 (13)	0.20690 (12)	0.28502 (12)	0.0321 (3)
Br1	0.1261 (2)	0.47367 (16)	0.19026 (18)	0.0424 (4)
Br2	0.3633 (2)	0.26600 (18)	0.3779 (2)	0.0491 (4)
N1	0.2025 (13)	−0.0210 (11)	0.3616 (12)	0.028 (2)
N2	0.0139 (13)	0.1409 (13)	0.2168 (14)	0.036 (3)
C1	0.3048 (18)	−0.0927 (14)	0.4310 (15)	0.036 (3)
H1	0.3742	−0.0363	0.4462	0.043*
C2	0.3107 (19)	−0.2513 (16)	0.4819 (17)	0.042 (4)
H2	0.3822	−0.3021	0.5325	0.051*
C3	0.2123 (18)	−0.3299 (16)	0.4572 (17)	0.043 (4)
H3	0.2171	−0.4369	0.4870	0.052*
C4	0.1059 (19)	−0.2536 (15)	0.3888 (16)	0.039 (3)
H4	0.0338	−0.3090	0.3760	0.047*
C5	0.1007 (15)	−0.0985 (15)	0.3378 (15)	0.033 (3)
C6	−0.0030 (16)	−0.0117 (16)	0.2607 (16)	0.036 (3)
C7	−0.1125 (18)	−0.0734 (18)	0.2308 (17)	0.043 (4)
H7	−0.1228	−0.1793	0.2599	0.052*
C8	−0.210 (2)	0.0237 (19)	0.1559 (18)	0.050 (4)
H8	−0.2888	−0.0153	0.1361	0.060*
C9	−0.188 (2)	0.1730 (18)	0.1129 (18)	0.049 (4)
H9	−0.2510	0.2396	0.0603	0.059*
C10	−0.0763 (18)	0.2292 (19)	0.1449 (17)	0.043 (4)
H10	−0.0636	0.3348	0.1143	0.051*
C11	0.5407 (19)	0.6259 (17)	0.1286 (19)	0.048 (4)
H11A	0.4406	0.5743	0.2001	0.058*
H11B	0.5875	0.5785	0.0437	0.058*
Cl1	0.4918 (5)	0.8180 (5)	0.0621 (5)	0.0515 (10)
Cl2	0.6808 (6)	0.6039 (5)	0.2181 (6)	0.0662 (13)

	U11	U22	U33	U12	U13	U23
Pd1	0.0322 (6)	0.0287 (5)	0.0372 (6)	−0.0048 (4)	−0.0124 (5)	−0.0096 (4)
Br1	0.0503 (9)	0.0281 (7)	0.0507 (10)	−0.0036 (6)	−0.0195 (7)	−0.0104 (6)
Br2	0.0533 (10)	0.0378 (8)	0.0684 (12)	−0.0122 (7)	−0.0345 (9)	−0.0089 (8)
N1	0.032 (6)	0.015 (5)	0.033 (6)	−0.001 (4)	−0.017 (5)	0.004 (4)
N2	0.022 (6)	0.040 (7)	0.053 (8)	−0.006 (5)	−0.013 (5)	−0.018 (6)
C1	0.051 (9)	0.015 (6)	0.037 (8)	−0.003 (6)	−0.018 (7)	0.004 (5)
C2	0.047 (9)	0.027 (7)	0.052 (10)	0.004 (6)	−0.024 (8)	−0.003 (6)
C3	0.045 (9)	0.024 (7)	0.042 (9)	−0.001 (6)	0.002 (7)	−0.005 (6)
C4	0.055 (9)	0.024 (7)	0.036 (8)	−0.003 (6)	−0.021 (7)	0.001 (6)
C5	0.020 (6)	0.041 (8)	0.040 (8)	−0.006 (6)	−0.001 (5)	−0.024 (6)
C6	0.027 (7)	0.040 (8)	0.041 (8)	−0.010 (6)	−0.009 (6)	−0.011 (6)
C7	0.041 (9)	0.046 (9)	0.043 (9)	−0.011 (7)	−0.016 (7)	−0.006 (7)
C8	0.053 (10)	0.053 (10)	0.055 (11)	−0.008 (8)	−0.035 (9)	−0.007 (8)
C9	0.051 (10)	0.048 (9)	0.054 (10)	−0.010 (8)	−0.034 (8)	0.006 (8)
C10	0.045 (9)	0.059 (10)	0.045 (9)	−0.007 (7)	−0.037 (7)	−0.014 (7)
C11	0.041 (9)	0.045 (9)	0.055 (10)	−0.016 (7)	−0.004 (8)	−0.018 (8)
Cl1	0.055 (2)	0.045 (2)	0.055 (3)	−0.0045 (18)	−0.026 (2)	−0.0050 (18)
Cl2	0.069 (3)	0.052 (3)	0.091 (4)	0.003 (2)	−0.052 (3)	−0.008 (2)

Pd1—N1	2.042 (9)	C4—H4	0.9500
Pd1—N2	2.051 (11)	C5—C6	1.43 (2)
Pd1—Br2	2.4044 (19)	C6—C7	1.371 (19)
Pd1—Br1	2.4182 (18)	C7—C8	1.41 (2)
N1—C1	1.338 (17)	C7—H7	0.9500
N1—C5	1.370 (15)	C8—C9	1.35 (2)
N2—C10	1.317 (18)	C8—H8	0.9500
N2—C6	1.371 (17)	C9—C10	1.373 (19)
C1—C2	1.412 (17)	C9—H9	0.9500
C1—H1	0.9500	C10—H10	0.9500
C2—C3	1.36 (2)	C11—Cl2	1.757 (17)
C2—H2	0.9500	C11—Cl1	1.763 (16)
C3—C4	1.37 (2)	C11—H11A	0.9900
C3—H3	0.9500	C11—H11B	0.9900
C4—C5	1.382 (18)
N1—Pd1—N2	80.6 (5)	N1—C5—C4	117.9 (13)
N1—Pd1—Br2	95.3 (3)	N1—C5—C6	117.2 (12)
N2—Pd1—Br2	175.7 (4)	C4—C5—C6	124.9 (12)
N1—Pd1—Br1	175.7 (3)	C7—C6—N2	120.9 (14)
N2—Pd1—Br1	95.1 (3)	C7—C6—C5	123.7 (13)
Br2—Pd1—Br1	88.90 (6)	N2—C6—C5	115.4 (12)
C1—N1—C5	121.3 (11)	C6—C7—C8	118.5 (15)
C1—N1—Pd1	125.6 (9)	C6—C7—H7	120.7
C5—N1—Pd1	113.0 (9)	C8—C7—H7	120.7
C10—N2—C6	119.5 (12)	C9—C8—C7	118.9 (15)
C10—N2—Pd1	126.8 (10)	C9—C8—H8	120.6
C6—N2—Pd1	113.6 (10)	C7—C8—H8	120.6
N1—C1—C2	120.6 (13)	C8—C9—C10	120.3 (15)
N1—C1—H1	119.7	C8—C9—H9	119.8
C2—C1—H1	119.7	C10—C9—H9	119.8
C3—C2—C1	118.8 (14)	N2—C10—C9	121.9 (15)
C3—C2—H2	120.6	N2—C10—H10	119.1
C1—C2—H2	120.6	C9—C10—H10	119.1
C2—C3—C4	119.4 (13)	Cl2—C11—Cl1	110.9 (8)
C2—C3—H3	120.3	Cl2—C11—H11A	109.5
C4—C3—H3	120.3	Cl1—C11—H11A	109.5
C3—C4—C5	121.9 (14)	Cl2—C11—H11B	109.5
C3—C4—H4	119.1	Cl1—C11—H11B	109.5
C5—C4—H4	119.1	H11A—C11—H11B	108.0
N2—Pd1—N1—C1	178.3 (12)	C3—C4—C5—N1	−2(2)
Br2—Pd1—N1—C1	−3.1 (11)	C3—C4—C5—C6	177.7 (14)
N2—Pd1—N1—C5	−2.9 (9)	C10—N2—C6—C7	0(2)
Br2—Pd1—N1—C5	175.6 (8)	Pd1—N2—C6—C7	176.6 (11)
N1—Pd1—N2—C10	179.9 (13)	C10—N2—C6—C5	179.8 (13)
Br1—Pd1—N2—C10	0.6 (13)	Pd1—N2—C6—C5	−3.5 (15)
N1—Pd1—N2—C6	3.5 (9)	N1—C5—C6—C7	−179.1 (13)
Br1—Pd1—N2—C6	−175.8 (9)	C4—C5—C6—C7	1(2)
C5—N1—C1—C2	0(2)	N1—C5—C6—N2	1.1 (18)
Pd1—N1—C1—C2	178.7 (10)	C4—C5—C6—N2	−178.6 (13)
N1—C1—C2—C3	1(2)	N2—C6—C7—C8	−1(2)
C1—C2—C3—C4	−2(2)	C5—C6—C7—C8	179.1 (14)
C2—C3—C4—C5	3(2)	C6—C7—C8—C9	2(2)
C1—N1—C5—C4	0.4 (19)	C7—C8—C9—C10	−2(3)
Pd1—N1—C5—C4	−178.4 (10)	C6—N2—C10—C9	0(2)
C1—N1—C5—C6	−179.2 (12)	Pd1—N2—C10—C9	−175.8 (12)
Pd1—N1—C5—C6	2.0 (15)	C8—C9—C10—N2	0(3)

D—H···A	D—H	H···A	D···A	D—H···A
C1—H1···Br2	0.95	2.69	3.313 (13)	124
C2—H2···Br2i	0.95	2.84	3.659 (16)	145
C10—H10···Br1	0.95	2.72	3.343 (14)	124
C11—H11A···Br2	0.99	2.92	3.693 (15)	135
C11—H11B···Br1ii	0.99	2.81	3.668 (16)	145

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C1—H1⋯Br2	0.95	2.69	3.313 (13)	124
C2—H2⋯Br2i	0.95	2.84	3.659 (16)	145
C10—H10⋯Br1	0.95	2.72	3.343 (14)	124
C11—H11A⋯Br2	0.99	2.92	3.693 (15)	135
C11—H11B⋯Br1ii	0.99	2.81	3.668 (16)	145

Symmetry codes: (i) ; (ii) .