Bis{2-[(phenyl-imino)-meth-yl]-1H-pyrrol-1-ido}palladium(II).

In the title complex, [Pd(C11H9N2)2], the Pd(II) atom is located on an inversion centre and has a square-planar coordination geometry. The phenyl substituents at the imine N atoms make a dihedral angle of 75.0 (6)° with respect to the PdN4 plane.

Related literature

For structure analyses of the free ligand N-[(1H-pyrrol-2-yl)methyl­ene]aniline, see: Gomes et al. (2010 ▶); Crestani et al. (2011 ▶). For the structure of a related nickel complex of the same imine ligand and an additional bipyridine ligand, see: Castro et al. (1992 ▶). For the structure of a related palladium complex with a different aromatic substituent, see: Liang et al. (2004 ▶).

Experimental

Crystal data

[Pd(C11H9N2)2]

M = 444.80

Monoclinic,

a = 10.5634 (4) Å

b = 10.6480 (6) Å

c = 8.0560 (7) Å

β = 93.044 (2)°

V = 904.85 (10) Å3

Z = 2

Mo Kα radiation

μ = 1.04 mm−1

T = 183 K

0.60 × 0.10 × 0.02 mm

Data collection

Nonius KappaCCD diffractometer

3903 measured reflections

2018 independent reflections

1464 reflections with I > 2σ(I)

R int = 0.035

Refinement

R[F 2 > 2σ(F 2)] = 0.032

wR(F 2) = 0.078

S = 1.00

2018 reflections

124 parameters

H-atom parameters constrained

Δρmax = 0.31 e Å−3

Δρmin = −0.75 e Å−3

Data collection: COLLECT (Nonius, 1998 ▶); cell refinement: DENZO (Otwinowski & Minor, 1997 ▶); data reduction: DENZO; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: ORTEP-3 (Farrugia, 2012 ▶); software used to prepare material for publication: publCIF (Westrip, 2010 ▶).

Click here for additional data file.

Crystal structure: contains datablock(s) I, global. DOI: 10.1107/S1600536812048143/su2533sup1.cif

Click here for additional data file.

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536812048143/su2533Isup2.hkl

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

[Pd(C11H9N2)2]	F(000) = 448
Mr = 444.80	Dx = 1.633 Mg m−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 3903 reflections
a = 10.5634 (4) Å	θ = 2.7–27.5°
b = 10.6480 (6) Å	µ = 1.04 mm−1
c = 8.0560 (7) Å	T = 183 K
β = 93.044 (2)°	Plate, yellow
V = 904.85 (10) Å3	0.6 × 0.1 × 0.02 mm
Z = 2

Nonius KappaCCD diffractometer	1464 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	Rint = 0.035
Graphite monochromator	θmax = 27.5°, θmin = 2.7°
phi–scan, ω–scan	h = −13→13
3903 measured reflections	k = −13→13
2018 independent reflections	l = 0→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)] = 0.032	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.078	H-atom parameters constrained
S = 1.00	w = 1/[σ2(Fo2) + (0.0376P)2 + ] where P = (Fo2 + 2Fc2)/3
2018 reflections	(Δ/σ)max < 0.001
124 parameters	Δρmax = 0.31 e Å−3
0 restraints	Δρmin = −0.75 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	0.5000	0.5000	0.0000	0.02321 (12)
N1	0.6789 (2)	0.5646 (2)	0.0414 (3)	0.0262 (6)
C1	0.7967 (3)	0.5447 (3)	−0.0074 (4)	0.0312 (7)
H1	0.8188	0.4863	−0.0902	0.037*
C2	0.8824 (3)	0.6229 (3)	0.0821 (4)	0.0315 (7)
H2	0.9714	0.6268	0.0707	0.038*
C3	0.8136 (3)	0.6933 (3)	0.1901 (4)	0.0321 (7)
H3	0.8457	0.7552	0.2662	0.038*
C4	0.6880 (3)	0.6555 (3)	0.1652 (3)	0.0285 (7)
C5	0.5768 (3)	0.6762 (3)	0.2483 (3)	0.0299 (7)
H5	0.5744	0.7365	0.3349	0.036*
N2	0.4762 (2)	0.6101 (2)	0.2034 (3)	0.0270 (6)
C6	0.3624 (3)	0.6222 (3)	0.2888 (3)	0.0280 (7)
C7	0.3223 (3)	0.5215 (3)	0.3841 (4)	0.0339 (8)
H7	0.3735	0.4486	0.3975	0.041*
C8	0.2079 (4)	0.5286 (3)	0.4586 (4)	0.0385 (8)
H8	0.1811	0.4606	0.5245	0.046*
C9	0.1314 (3)	0.6348 (3)	0.4379 (4)	0.0395 (8)
H9	0.0511	0.6382	0.4858	0.047*
C10	0.1739 (3)	0.7353 (3)	0.3466 (4)	0.0363 (8)
H10	0.1232	0.8088	0.3350	0.044*
C11	0.2885 (3)	0.7303 (3)	0.2724 (3)	0.0300 (7)
H11	0.3168	0.8000	0.2107	0.036*

	U11	U22	U33	U12	U13	U23
Pd1	0.02423 (19)	0.02118 (18)	0.02387 (18)	−0.00028 (14)	−0.00192 (12)	−0.00276 (13)
N1	0.0275 (14)	0.0234 (14)	0.0274 (12)	−0.0012 (11)	−0.0018 (11)	0.0008 (10)
C1	0.0302 (18)	0.0304 (15)	0.0328 (16)	0.0010 (14)	−0.0002 (14)	0.0008 (13)
C2	0.0240 (16)	0.0340 (17)	0.0361 (16)	−0.0078 (14)	−0.0021 (14)	0.0057 (13)
C3	0.0318 (18)	0.0316 (18)	0.0319 (16)	−0.0076 (14)	−0.0064 (14)	−0.0004 (13)
C4	0.0356 (18)	0.0226 (15)	0.0268 (14)	−0.0029 (13)	−0.0027 (14)	−0.0022 (12)
C5	0.0338 (18)	0.0272 (16)	0.0283 (15)	−0.0008 (13)	−0.0029 (14)	−0.0042 (12)
N2	0.0290 (14)	0.0246 (13)	0.0271 (13)	0.0011 (11)	−0.0009 (11)	−0.0037 (10)
C6	0.0286 (16)	0.0311 (17)	0.0238 (14)	−0.0030 (13)	−0.0024 (13)	−0.0076 (12)
C7	0.0372 (19)	0.035 (2)	0.0297 (16)	0.0033 (14)	0.0008 (14)	0.0003 (12)
C8	0.045 (2)	0.039 (2)	0.0308 (17)	−0.0062 (15)	0.0028 (16)	0.0030 (13)
C9	0.0298 (18)	0.055 (2)	0.0340 (16)	−0.0047 (16)	0.0056 (14)	−0.0123 (15)
C10	0.0348 (19)	0.039 (2)	0.0351 (17)	0.0095 (15)	−0.0014 (15)	−0.0080 (14)
C11	0.0339 (18)	0.0276 (17)	0.0281 (15)	0.0026 (14)	−0.0020 (14)	−0.0035 (12)

Pd1—N1	2.022 (2)	C5—H5	0.9500
Pd1—N1i	2.022 (2)	N2—C6	1.422 (4)
Pd1—N2	2.041 (2)	C6—C11	1.393 (4)
Pd1—N2i	2.041 (2)	C6—C7	1.398 (4)
N1—C1	1.342 (4)	C7—C8	1.379 (5)
N1—C4	1.389 (3)	C7—H7	0.9500
C1—C2	1.401 (4)	C8—C9	1.395 (5)
C1—H1	0.9500	C8—H8	0.9500
C2—C3	1.384 (4)	C9—C10	1.387 (5)
C2—H2	0.9500	C9—H9	0.9500
C3—C4	1.391 (4)	C10—C11	1.379 (4)
C3—H3	0.9500	C10—H10	0.9500
C4—C5	1.400 (4)	C11—H11	0.9500
C5—N2	1.310 (4)
N1—Pd1—N1i	180.0	C4—C5—H5	120.9
N1—Pd1—N2	80.00 (9)	C5—N2—C6	120.8 (2)
N1i—Pd1—N2	100.00 (9)	C5—N2—Pd1	113.4 (2)
N1—Pd1—N2i	100.00 (9)	C6—N2—Pd1	125.75 (18)
N1i—Pd1—N2i	80.00 (9)	C11—C6—C7	120.1 (3)
N2—Pd1—N2i	180.0	C11—C6—N2	120.9 (3)
C1—N1—C4	106.9 (3)	C7—C6—N2	119.0 (3)
C1—N1—Pd1	140.5 (2)	C8—C7—C6	119.7 (3)
C4—N1—Pd1	112.6 (2)	C8—C7—H7	120.1
N1—C1—C2	109.8 (3)	C6—C7—H7	120.1
N1—C1—H1	125.1	C9—C8—C7	120.5 (3)
C2—C1—H1	125.1	C9—C8—H8	119.7
C3—C2—C1	107.4 (3)	C7—C8—H8	119.7
C3—C2—H2	126.3	C10—C9—C8	119.1 (3)
C1—C2—H2	126.3	C10—C9—H9	120.4
C2—C3—C4	106.3 (3)	C8—C9—H9	120.4
C2—C3—H3	126.8	C9—C10—C11	121.1 (3)
C4—C3—H3	126.8	C9—C10—H10	119.4
N1—C4—C3	109.5 (3)	C11—C10—H10	119.4
N1—C4—C5	115.2 (3)	C6—C11—C10	119.4 (3)
C3—C4—C5	134.7 (3)	C6—C11—H11	120.3
N2—C5—C4	118.2 (3)	C10—C11—H11	120.3
N2—C5—H5	120.9