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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.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536807008483/dn2131sup1.cif
Contains datablocks I, global

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536807008483/dn2131Isup2.hkl
Contains datablock I

CCDC reference: 640319

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

Computing details top

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) top
Crystal data top
(C10H10N2)[PdCl4]F(000) = 396
Mr = 406.40Dx = 2.133 Mg m3
Monoclinic, I2/mMo Kα radiation, λ = 0.71073 Å
Hall symbol: -I 2yCell parameters from 2186 reflections
a = 6.718 (1) Åθ = 3.1–25.4°
b = 11.754 (2) ŵ = 2.29 mm1
c = 8.015 (2) ÅT = 298 K
β = 90.649 (3)°Prism, yellow
V = 632.9 (2) Å30.19 × 0.08 × 0.07 mm
Z = 2
Data collection top
Bruker SMART APEX CCD
diffractometer
613 independent reflections
Radiation source: fine-focus sealed tube591 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.037
Detector resolution: 0.661 pixels mm-1θmax = 25.4°, θmin = 3.1°
ω scansh = 88
Absorption correction: analytical
(Sheldrick, 2000)
k = 1414
Tmin = 0.670, Tmax = 0.855l = 99
2552 measured reflections
Refinement top
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.023Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.058H atoms treated by a mixture of independent and constrained refinement
S = 1.10 w = 1/[σ2(Fo2) + (0.0295P)2 + 0.5871P]
where P = (Fo2 + 2Fc2)/3
613 reflections(Δ/σ)max < 0.001
46 parametersΔρmax = 0.58 e Å3
1 restraintΔρmin = 0.29 e Å3
Special details top

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 (Å2) top
xyzUiso*/Ueq
Pd11.00000.00000.00000.03097 (18)
Cl10.79728 (13)0.13796 (7)0.10751 (11)0.0519 (3)
N10.4434 (6)0.00000.2829 (5)0.0489 (10)
H10.558 (4)0.00000.234 (6)0.059*
C20.3630 (5)0.0972 (3)0.3246 (5)0.0560 (9)
H20.42430.16510.29500.067*
C30.1888 (5)0.0993 (3)0.4116 (5)0.0502 (8)
H30.13300.16860.44170.060*
C40.0965 (6)0.00000.4544 (5)0.0333 (9)
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Pd10.0321 (3)0.0306 (3)0.0304 (3)0.0000.00733 (17)0.000
Cl10.0506 (6)0.0374 (5)0.0684 (6)0.0049 (3)0.0275 (4)0.0009 (4)
N10.035 (2)0.074 (3)0.038 (2)0.0000.0092 (16)0.000
C20.048 (2)0.056 (2)0.065 (2)0.0062 (18)0.0137 (17)0.0120 (18)
C30.0444 (19)0.0395 (19)0.067 (2)0.0008 (14)0.0182 (16)0.0016 (16)
C40.034 (2)0.036 (2)0.0301 (19)0.0000.0019 (16)0.000
Geometric parameters (Å, º) top
Pd1—Cl12.2920 (8)C2—H20.9300
N1—C2i1.309 (4)C3—C41.367 (4)
N1—C21.309 (4)C3—H30.9300
N1—H10.87 (3)C4—C3i1.367 (4)
C2—C31.369 (5)C4—C4ii1.496 (8)
Cl1iii—Pd1—Cl189.94 (4)C3—C2—H2119.9
Cl1i—Pd1—Cl190.06 (4)C4—C3—C2120.3 (3)
Cl1iv—Pd1—Cl1180.00 (5)C4—C3—H3119.8
C2i—N1—C2121.6 (4)C2—C3—H3119.8
C2i—N1—H1119.1 (3)C3i—C4—C3117.2 (4)
C2—N1—H1119.1 (3)C3i—C4—C4ii121.4 (2)
N1—C2—C3120.2 (4)C3—C4—C4ii121.4 (2)
N1—C2—H2119.9
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) top
D—H···AD—HH···AD···AD—H···A
N1—H1···Cl10.87 (3)2.51 (3)3.214 (3)139 (1)
 

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