4,4′-Bipyridinium tetra­chloridopalladate(II)

In the title compound, (C₁₀H₁₀N₂)[PdCl₄], the Pd atom in the tetra­chloridopalladate anion exhibits a square-planar geometry. The anion is hydrogen bonded to the bipyridinium cation by an N—H...Cl hydrogen bond to form chains. The bipyridinium cation and the tetra­chloridopalladate anion exhibit perfect 2/m symmetry with the Pd atom located on a 2/m symmetry site.

Key indicators

• Single-crystal X-ray study
• T = 298 K
• Mean [sigma](C-C) = 0.005 Å
• R factor = 0.023
• wR factor = 0.058
• Data-to-parameter ratio = 13.3

checkCIF/PLATON results

No syntax errors found



Alert level C
PLAT128_ALERT_4_C Non-standard setting of Space group C2/m    ....    I2/m

   0 ALERT level A = In general: serious problem
   0 ALERT level B = Potentially serious problem
   1 ALERT level C = Check and explain
   0 ALERT level G = General alerts; check

   0 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
   0 ALERT type 2 Indicator that the structure model may be wrong or deficient
   0 ALERT type 3 Indicator that the structure quality may be low
   1 ALERT type 4 Improvement, methodology, query or suggestion
   0 ALERT type 5 Informative message, check

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Computing details

Data collection: SMART (Bruker, 2006); cell refinement: SMART; data reduction: SAINT (Bruker, 2006); program(s) used to solve structure: SHELXTL (Sheldrick, 2000); program(s) used to refine structure: SHELXTL; molecular graphics: X-SEED (Barbour, 2001); software used to prepare material for publication: publCIF Westrip, 2007) and enCIFer (Allen et al., 2004).

4,4'-Bipyridinium tetrachloridopalladate(II)

Crystal data

(C10H10N2)[PdCl4]	F(000) = 396
Mr = 406.40	Dx = 2.133 Mg m^−3
Monoclinic, I2/m	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -I 2y	Cell parameters from 2186 reflections
a = 6.718 (1) Å	θ = 3.1–25.4°
b = 11.754 (2) Å	µ = 2.29 mm^−1
c = 8.015 (2) Å	T = 298 K
β = 90.649 (3)°	Prism, yellow
V = 632.9 (2) Å^3	0.19 × 0.08 × 0.07 mm
Z = 2

Data collection

Bruker SMART APEX CCD diffractometer	613 independent reflections
Radiation source: fine-focus sealed tube	591 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.037
Detector resolution: 0.661 pixels mm^-1	θmax = 25.4°, θmin = 3.1°
ω scans	h = −8→8
Absorption correction: analytical (Sheldrick, 2000)	k = −14→14
Tmin = 0.670, Tmax = 0.855	l = −9→9
2552 measured reflections

Refinement

Refinement on F^2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F^2 > 2σ(F^2)] = 0.023	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.058	H atoms treated by a mixture of independent and constrained refinement
S = 1.10	w = 1/[σ^2(Fo^2) + (0.0295P)^2 + 0.5871P] where P = (Fo^2 + 2Fc^2)/3
613 reflections	(Δ/σ)max < 0.001
46 parameters	Δρmax = 0.58 e Å^−3
1 restraint	Δρmin = −0.29 e Å^−3

Special details

Experimental. The non-standard setting I2/m for the space group C2/m was selected following the suggestions of Alan D. Mighell (Mighell, 2002) for monoclinic conventional cells

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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Ų)

	x	y	z	Uiso*/Ueq
Pd1	1.0000	0.0000	0.0000	0.03097 (18)
Cl1	0.79728 (13)	0.13796 (7)	0.10751 (11)	0.0519 (3)
N1	0.4434 (6)	0.0000	0.2829 (5)	0.0489 (10)
H1	0.558 (4)	0.0000	0.234 (6)	0.059*
C2	0.3630 (5)	0.0972 (3)	0.3246 (5)	0.0560 (9)
H2	0.4243	0.1651	0.2950	0.067*
C3	0.1888 (5)	0.0993 (3)	0.4116 (5)	0.0502 (8)
H3	0.1330	0.1686	0.4417	0.060*
C4	0.0965 (6)	0.0000	0.4544 (5)	0.0333 (9)

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
Pd1	0.0321 (3)	0.0306 (3)	0.0304 (3)	0.000	0.00733 (17)	0.000
Cl1	0.0506 (6)	0.0374 (5)	0.0684 (6)	0.0049 (3)	0.0275 (4)	−0.0009 (4)
N1	0.035 (2)	0.074 (3)	0.038 (2)	0.000	0.0092 (16)	0.000
C2	0.048 (2)	0.056 (2)	0.065 (2)	−0.0062 (18)	0.0137 (17)	0.0120 (18)
C3	0.0444 (19)	0.0395 (19)	0.067 (2)	−0.0008 (14)	0.0182 (16)	0.0016 (16)
C4	0.034 (2)	0.036 (2)	0.0301 (19)	0.000	0.0019 (16)	0.000

Geometric parameters (Å, º)

Pd1—Cl1	2.2920 (8)	C2—H2	0.9300
N1—C2^i	1.309 (4)	C3—C4	1.367 (4)
N1—C2	1.309 (4)	C3—H3	0.9300
N1—H1	0.87 (3)	C4—C3^i	1.367 (4)
C2—C3	1.369 (5)	C4—C4^ii	1.496 (8)
Cl1^iii—Pd1—Cl1	89.94 (4)	C3—C2—H2	119.9
Cl1^i—Pd1—Cl1	90.06 (4)	C4—C3—C2	120.3 (3)
Cl1^iv—Pd1—Cl1	180.00 (5)	C4—C3—H3	119.8
C2^i—N1—C2	121.6 (4)	C2—C3—H3	119.8
C2^i—N1—H1	119.1 (3)	C3^i—C4—C3	117.2 (4)
C2—N1—H1	119.1 (3)	C3^i—C4—C4^ii	121.4 (2)
N1—C2—C3	120.2 (4)	C3—C4—C4^ii	121.4 (2)
N1—C2—H2	119.9

Symmetry codes: (i) x, −y, z; (ii) −x, −y, −z+1; (iii) −x+2, y, −z; (iv) −x+2, −y, −z.

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1···Cl1	0.87 (3)	2.51 (3)	3.214 (3)	139 (1)