trans-Dibromidobis(1-ethyl-3-methyl-imidazol-2-yl-idene)palladium(II).

The title compound, trans-[PdBr(2)(C(6)H(10)N(2))(2)], was synthesized ionothermally in the ionic liquid solvent 1-ethyl-3-methyl-imidazolium bromide. In the crystal, the Pd(II) atoms are square-planarly coordinated to two Br atoms and two neutral (C(6)H(10)N(2)) ligands. The Pd(II) atom is located on an inversion centre.

Related literature

The title complex shares many features with a number of known structures, which also contain a PdII atom square-planarly coordinated to two bromide ligands in trans-conformation as well as two equivalent organic ligands (Hahn et al., 2004 ▶; Huynh & Wu, 2009 ▶). A few of these structures even have the same space group and in some structures the organic ligand is also an imidazolium derivative (Dash et al., 2010 ▶). The title compound was obtained in a attempt to simplify the synthesis of the cis-complex which was described previously (Madsen et al., 2011 ▶). For information on the ionothermal synthesis method, see: Welton (1999 ▶); Babai & Mudring (2006 ▶); Morris (2009 ▶).

Experimental

Crystal data

[PdBr2(C6H10N2)2]

M = 486.54

Monoclinic,

a = 8.3093 (2) Å

b = 8.6868 (2) Å

c = 12.0788 (3) Å

β = 101.741 (1)°

V = 853.62 (4) Å3

Z = 2

Mo Kα radiation

μ = 5.76 mm−1

T = 296 K

0.15 × 0.15 × 0.1 mm

Data collection

Bruker X8 APEXII diffractometer

Absorption correction: multi-scan (SADABS; Sheldrick, 2008a ▶) T min = 0.585, T max = 0.711

27485 measured reflections

2582 independent reflections

1894 reflections with I > 2σ(I)

R int = 0.022

Refinement

R[F 2 > 2σ(F 2)] = 0.044

wR(F 2) = 0.167

S = 1.63

2582 reflections

88 parameters

H-atom parameters constrained

Δρmax = 1.84 e Å−3

Δρmin = −1.02 e Å−3

Data collection: APEX2 (Bruker, 2011 ▶); cell refinement: SAINT (Bruker, 2011 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008b ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008b ▶); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997 ▶) and Mercury (Macrae et al., 2006 ▶); software used to prepare material for publication: WinGX (Farrugia, 1999 ▶).

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S1600536811030480/zk2019sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536811030480/zk2019Isup2.hkl

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

[PdBr2(C6H10N2)2]	F(000) = 472
Mr = 486.54	Dx = 1.893 Mg m−3
Monoclinic, P21/n	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2yn	Cell parameters from 9872 reflections
a = 8.3093 (2) Å	θ = 5.5–54.7°
b = 8.6868 (2) Å	µ = 5.76 mm−1
c = 12.0788 (3) Å	T = 296 K
β = 101.741 (1)°	Square, colourless
V = 853.62 (4) Å3	0.15 × 0.15 × 0.1 mm
Z = 2

Bruker X8 APEXII diffractometer	2582 independent reflections
Radiation source: fine-focus sealed tube	1894 reflections with I > 2σ(I)
graphite	Rint = 0.022
Detector resolution: 12.00 pixels mm-1	θmax = 30.5°, θmin = 2.7°
Narrow slices collected using φ and ω scans	h = −11→11
Absorption correction: multi-scan (SADABS; Sheldrick, 2008a)	k = −12→12
Tmin = 0.585, Tmax = 0.711	l = −15→17
27485 measured reflections

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)] = 0.044	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.167	H-atom parameters constrained
S = 1.63	w = 1/[σ2(Fo2) + (0.0705P)2] where P = (Fo2 + 2Fc2)/3
2582 reflections	(Δ/σ)max = 0.008
88 parameters	Δρmax = 1.84 e Å−3
0 restraints	Δρmin = −1.02 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
N2	0.8710 (5)	0.9917 (3)	0.7471 (3)	0.0598 (9)
C1	0.9896 (5)	0.9475 (5)	0.8355 (3)	0.0570 (8)
C3	0.9059 (7)	0.9436 (6)	0.6478 (4)	0.0735 (11)
H3	0.8411	0.9594	0.5763	0.088*
C5	1.2461 (7)	0.7839 (10)	0.8505 (6)	0.118 (2)
H5A	1.2269	0.747	0.9225	0.142*
H5B	1.2675	0.6958	0.8062	0.142*
C2	1.0451 (6)	0.8718 (7)	0.6700 (4)	0.0852 (14)
H2	1.1002	0.8294	0.6176	0.102*
C6	1.3777 (13)	0.8815 (14)	0.8675 (10)	0.197 (5)
H6A	1.473	0.8289	0.9084	0.295*
H6B	1.3548	0.9691	0.9104	0.295*
H6C	1.3977	0.9152	0.7959	0.295*
C4	0.7242 (7)	1.0768 (7)	0.7604 (5)	0.0953 (17)
H4A	0.6572	1.0973	0.6873	0.143*
H4B	0.7563	1.1723	0.7986	0.143*
H4C	0.6629	1.0166	0.8041	0.143*
Br1	1.09068 (7)	1.25854 (6)	0.96387 (4)	0.0893 (2)
N1	1.0978 (4)	0.8699 (5)	0.7886 (3)	0.0772 (10)
Pd1	1	1	1	0.0555 (2)

	U11	U22	U33	U12	U13	U23
N2	0.075 (2)	0.060 (2)	0.0438 (19)	0.0033 (13)	0.0110 (16)	0.0020 (13)
C1	0.064 (2)	0.063 (2)	0.047 (2)	−0.0089 (17)	0.0168 (16)	−0.0047 (18)
C3	0.104 (4)	0.073 (3)	0.044 (2)	−0.009 (3)	0.016 (2)	−0.002 (2)
C5	0.080 (3)	0.189 (7)	0.088 (4)	0.017 (4)	0.023 (3)	−0.011 (4)
C2	0.100 (4)	0.104 (4)	0.059 (3)	−0.001 (3)	0.033 (3)	−0.006 (3)
C6	0.136 (7)	0.207 (12)	0.231 (13)	−0.009 (9)	0.000 (7)	0.036 (9)
C4	0.104 (4)	0.114 (4)	0.064 (3)	0.052 (4)	0.010 (3)	0.006 (3)
Br1	0.1261 (5)	0.0831 (4)	0.0624 (4)	−0.0312 (3)	0.0278 (3)	−0.0070 (2)
N1	0.0732 (19)	0.108 (3)	0.0529 (19)	0.008 (2)	0.0181 (16)	−0.0060 (19)
Pd1	0.0597 (3)	0.0696 (4)	0.0386 (3)	−0.00208 (16)	0.01357 (18)	−0.00364 (15)

N2—C1	1.353 (6)	C2—N1	1.410 (6)
N2—C3	1.356 (6)	C2—H2	0.93
N2—C4	1.463 (6)	C6—H6A	0.96
C1—N1	1.338 (5)	C6—H6B	0.96
C1—Pd1	2.023 (4)	C6—H6C	0.96
C3—C2	1.293 (7)	C4—H4A	0.96
C3—H3	0.93	C4—H4B	0.96
C5—C6	1.366 (12)	C4—H4C	0.96
C5—N1	1.503 (7)	Br1—Pd1	2.4364 (5)
C5—H5A	0.97	Pd1—C1i	2.023 (4)
C5—H5B	0.97	Pd1—Br1i	2.4364 (5)
C1—N2—C3	111.0 (4)	H6A—C6—H6B	109.5
C1—N2—C4	123.1 (4)	C5—C6—H6C	109.5
C3—N2—C4	125.9 (4)	H6A—C6—H6C	109.5
N1—C1—N2	104.7 (3)	H6B—C6—H6C	109.5
N1—C1—Pd1	129.1 (3)	N2—C4—H4A	109.5
N2—C1—Pd1	126.2 (3)	N2—C4—H4B	109.5
C2—C3—N2	107.9 (4)	H4A—C4—H4B	109.5
C2—C3—H3	126	N2—C4—H4C	109.5
N2—C3—H3	126	H4A—C4—H4C	109.5
C6—C5—N1	108.5 (8)	H4B—C4—H4C	109.5
C6—C5—H5A	110	C1—N1—C2	109.1 (4)
N1—C5—H5A	110	C1—N1—C5	126.4 (4)
C6—C5—H5B	110	C2—N1—C5	124.3 (4)
N1—C5—H5B	110	C1—Pd1—C1i	180.000 (2)
H5A—C5—H5B	108.4	C1—Pd1—Br1	89.14 (12)
C3—C2—N1	107.2 (4)	C1i—Pd1—Br1	90.86 (12)
C3—C2—H2	126.4	C1—Pd1—Br1i	90.86 (12)
N1—C2—H2	126.4	C1i—Pd1—Br1i	89.14 (12)
C5—C6—H6A	109.5	Br1—Pd1—Br1i	180
C5—C6—H6B	109.5
C3—N2—C1—N1	−0.5 (5)	Pd1—C1—N1—C5	8.6 (7)
C4—N2—C1—N1	178.1 (4)	C3—C2—N1—C1	−2.4 (6)
C3—N2—C1—Pd1	176.8 (3)	C3—C2—N1—C5	173.7 (5)
C4—N2—C1—Pd1	−4.7 (6)	C6—C5—N1—C1	−91.6 (8)
C1—N2—C3—C2	−1.1 (6)	C6—C5—N1—C2	93.0 (8)
C4—N2—C3—C2	−179.6 (5)	N1—C1—Pd1—Br1	100.3 (4)
N2—C3—C2—N1	2.1 (6)	N2—C1—Pd1—Br1	−76.2 (4)
N2—C1—N1—C2	1.7 (5)	N1—C1—Pd1—Br1i	−79.7 (4)
Pd1—C1—N1—C2	−175.4 (3)	N2—C1—Pd1—Br1i	103.8 (4)
N2—C1—N1—C5	−174.3 (5)

C1—Pd1	2.023 (4)
Br1—Pd1	2.4364 (5)

C1—Pd1—C1i	180
C1—Pd1—Br1	89.14 (12)
C1i—Pd1—Br1	90.86 (12)
Br1—Pd1—Br1i	180

Symmetry code: (i) .