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Acta Crystallogr Sect E Struct Rep Online. 2009 February 1; 65(Pt 2): m133.
Published online 2009 January 8. doi:  10.1107/S1600536808043523
PMCID: PMC2968331

2-(4-Pyridinio)benzimidazolium tetra­chloridopalladium(II)

Abstract

The asymmetric unit of the title compound, (C12H11N3)[PdCl4], consists of a 2-(4-pyridinio)benzimidazolium cation and two half [PdCl4]2− anions, which are located on inversion centres. The cations lie in sheets parallel to (An external file that holds a picture, illustration, etc.
Object name is e-65-0m133-efi1.jpg1An external file that holds a picture, illustration, etc.
Object name is e-65-0m133-efi1.jpg). The cations and anions are connected by N—H(...)Cl and C—H(...)Cl contacts.

Related literature

For related structures, see: Alcade et al. (1992 [triangle]); Chen et al. (2006 [triangle]); Huang et al. (2004 [triangle]); Wang et al. (1999 [triangle]).

An external file that holds a picture, illustration, etc.
Object name is e-65-0m133-scheme1.jpg

Experimental

Crystal data

  • (C12H11N3)[PdCl4]
  • M r = 445.44
  • Triclinic, An external file that holds a picture, illustration, etc.
Object name is e-65-0m133-efi3.jpg
  • a = 8.2221 (1) Å
  • b = 8.3964 (2) Å
  • c = 12.3768 (5) Å
  • α = 94.09 (3)°
  • β = 97.42 (2)°
  • γ = 116.102 (10)°
  • V = 752.95 (11) Å3
  • Z = 2
  • Mo Kα radiation
  • μ = 1.93 mm−1
  • T = 293 (2) K
  • 0.30 × 0.15 × 0.04 mm

Data collection

  • Rigaku Mercury CCD diffractometer
  • Absorption correction: multi-scan (CrystalClear; Rigaku, 2002 [triangle]) T min = 0.713, T max = 0.916
  • 5851 measured reflections
  • 3406 independent reflections
  • 2816 reflections with I > 2σ(I)
  • R int = 0.017

Refinement

  • R[F 2 > 2σ(F 2)] = 0.030
  • wR(F 2) = 0.074
  • S = 1.06
  • 3406 reflections
  • 184 parameters
  • H-atom parameters constrained
  • Δρmax = 0.81 e Å−3
  • Δρmin = −0.61 e Å−3

Data collection: CrystalClear (Rigaku, 2002 [triangle]); cell refinement: CrystalClear; data reduction: CrystalClear; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 [triangle]); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 [triangle]); molecular graphics: DIAMOND (Brandenburg & Putz, 2006 [triangle]) and SHELXTL (Sheldrick, 2008 [triangle]); software used to prepare material for publication: SHELXL97.

Table 1
Hydrogen-bond geometry (Å, °)

Supplementary Material

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536808043523/bt2834sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536808043523/bt2834Isup2.hkl

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

Acknowledgments

We gratefully acknowledge financial support by the Key Science and Technology Project of Fujian Province (No. 2005H045)

supplementary crystallographic information

Comment

The 2-(4-pyridyl)benzimidazole ligand is often used to act as terminal or bridging ligand in complexes, the noncoordinating N—H and N groups act as hydrogen bond donor or acceptor for the formation of hydrogen bonds, contributing to the crystal packing. Herein we report the synthesis and structure of title complex.

The asymmetry unit of the crystal structure of the title compound comprises one protonated 2-(4-pyridinio)benzimidazolium cation and two independent half [PdCl4]2- anion. Each PdII atom has a slightly distorted square planar coordination geometry (Fig. 1). The N—H···Cl interactions generate a two-dimensional sheet structure, as show in Fig. 2. The sheets are further connected into a three-dimensional network via C—H···Cl contacts (Fig. 3).

Experimental

An aqueous solution of PdCl2 10 ml (0.108 g, 0.61 mmol), 2-(4-pyridyl)benzimidazole (Alcade et al., 1992) (0.12 g, 0.61 mmol) and concentrated HCl (5 ml) was stirred continuously for about 30 min. the solution was allowed to stand at room temperature for several days and produced red crystals of the title compound (yield 85%).

Refinement

After checking their presence in the different map, all H atoms were fixed geometrically and allowed to ride on their parent atoms, with C—H = 0.93 Å, N—H = 0.86 Å, Uiso(H)=1.2Ueq(C,N).

Figures

Fig. 1.
The structure of the title compound with the atomic labels and 30% probability displacement ellipsoids for non-H atoms. Symmetry codes: (i) 2 - x, 2 - y, -z; (ii) -x, -y, 1 - z.
Fig. 2.
Hydrogen bond pattern of (I). The H atoms have been omitted for clarity; hydrogen bonds are shown as dashed lines.
Fig. 3.
The crystal packing of (I), the N—H···Cl interactions are shown as dashed lines.

Crystal data

(C12H11N3)[PdCl4]Z = 2
Mr = 445.44F(000) = 436
Triclinic, P1Dx = 1.964 Mg m3
Hall symbol: -P 1Mo Kα radiation, λ = 0.71073 Å
a = 8.2221 (1) ÅCell parameters from 1904 reflections
b = 8.3964 (2) Åθ = 3.3–27.5°
c = 12.3768 (5) ŵ = 1.93 mm1
α = 94.09 (3)°T = 293 K
β = 97.42 (2)°Prism, red
γ = 116.102 (10)°0.30 × 0.15 × 0.04 mm
V = 752.95 (11) Å3

Data collection

Rigaku Mercury CCD diffractometer3406 independent reflections
Radiation source: fine-focus sealed tube2816 reflections with I > 2σ(I)
graphiteRint = 0.017
ω scansθmax = 27.5°, θmin = 3.3°
Absorption correction: multi-scan (CrystalClear; Rigaku, 2002)h = −10→10
Tmin = 0.713, Tmax = 0.916k = −10→10
5851 measured reflectionsl = −16→15

Refinement

Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.030Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.074H-atom parameters constrained
S = 1.06w = 1/[σ2(Fo2) + (0.0306P)2 + 0.584P] where P = (Fo2 + 2Fc2)/3
3406 reflections(Δ/σ)max < 0.001
184 parametersΔρmax = 0.81 e Å3
0 restraintsΔρmin = −0.61 e Å3

Special details

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)

xyzUiso*/Ueq
Pd11.00001.00000.00000.02528 (9)
Pd20.00000.00000.50000.02595 (9)
C10.2054 (5)0.5925 (5)0.3660 (3)0.0415 (8)
H1B0.14250.56640.42480.050*
C20.2983 (5)0.7664 (4)0.3483 (3)0.0367 (7)
H2B0.29830.85860.39460.044*
C30.3925 (4)0.8040 (4)0.2610 (2)0.0281 (6)
C40.3862 (5)0.6625 (4)0.1924 (3)0.0389 (8)
H4A0.44680.68450.13250.047*
C50.2904 (5)0.4902 (4)0.2129 (3)0.0390 (8)
H5A0.28490.39470.16690.047*
C60.4975 (4)0.9893 (4)0.2438 (2)0.0269 (6)
C70.6195 (4)1.2852 (4)0.2627 (3)0.0318 (7)
C80.6740 (5)1.4663 (4)0.2955 (3)0.0428 (8)
H8A0.63201.50500.35320.051*
C90.7928 (5)1.5835 (5)0.2379 (4)0.0519 (10)
H9A0.83241.70560.25710.062*
C100.8567 (5)1.5272 (5)0.1519 (4)0.0523 (10)
H10A0.93401.61240.11370.063*
C110.8097 (5)1.3500 (5)0.1212 (3)0.0428 (8)
H11A0.85551.31300.06490.051*
C120.6896 (4)1.2291 (4)0.1793 (3)0.0326 (7)
N10.2050 (4)0.4609 (4)0.2996 (2)0.0376 (6)
H1A0.14750.35270.31280.045*
N20.5007 (3)1.1324 (3)0.2995 (2)0.0299 (6)
H2A0.43831.13000.35050.036*
N30.6107 (4)1.0441 (3)0.1709 (2)0.0305 (6)
H3A0.63130.97510.12580.037*
Cl10.69047 (11)0.81997 (12)−0.00991 (7)0.0429 (2)
Cl20.95830 (12)0.96403 (11)−0.18905 (6)0.0393 (2)
Cl30.30176 (11)0.19239 (11)0.48955 (7)0.03794 (19)
Cl4−0.09172 (12)0.20039 (11)0.43218 (7)0.0396 (2)

Atomic displacement parameters (Å2)

U11U22U33U12U13U23
Pd10.02766 (18)0.02197 (16)0.02590 (17)0.01006 (13)0.00961 (13)0.00102 (12)
Pd20.02897 (18)0.02667 (17)0.02514 (17)0.01380 (14)0.01011 (13)0.00409 (13)
C10.046 (2)0.0370 (18)0.0417 (19)0.0152 (16)0.0212 (16)0.0093 (15)
C20.044 (2)0.0273 (16)0.0375 (18)0.0135 (15)0.0144 (15)0.0000 (13)
C30.0252 (15)0.0271 (15)0.0322 (16)0.0113 (12)0.0079 (12)0.0042 (12)
C40.041 (2)0.0327 (17)0.0446 (19)0.0152 (15)0.0205 (16)0.0054 (15)
C50.044 (2)0.0293 (16)0.045 (2)0.0169 (15)0.0129 (16)−0.0019 (14)
C60.0248 (14)0.0272 (14)0.0292 (15)0.0119 (12)0.0059 (12)0.0036 (12)
C70.0278 (16)0.0287 (15)0.0382 (17)0.0123 (13)0.0045 (13)0.0077 (13)
C80.042 (2)0.0283 (17)0.059 (2)0.0178 (15)0.0087 (17)0.0022 (16)
C90.041 (2)0.0237 (16)0.084 (3)0.0088 (15)0.008 (2)0.0118 (18)
C100.043 (2)0.041 (2)0.071 (3)0.0129 (18)0.016 (2)0.027 (2)
C110.0372 (19)0.045 (2)0.047 (2)0.0156 (16)0.0148 (16)0.0177 (17)
C120.0295 (17)0.0289 (15)0.0392 (17)0.0125 (13)0.0065 (14)0.0077 (13)
N10.0400 (16)0.0259 (13)0.0485 (17)0.0138 (12)0.0150 (13)0.0101 (12)
N20.0311 (14)0.0261 (13)0.0356 (14)0.0144 (11)0.0118 (11)0.0031 (11)
N30.0338 (14)0.0278 (13)0.0322 (14)0.0140 (11)0.0141 (11)0.0045 (11)
Cl10.0280 (4)0.0474 (5)0.0406 (5)0.0061 (4)0.0134 (3)−0.0099 (4)
Cl20.0485 (5)0.0319 (4)0.0271 (4)0.0082 (4)0.0105 (3)0.0025 (3)
Cl30.0306 (4)0.0347 (4)0.0446 (5)0.0098 (3)0.0157 (4)−0.0004 (3)
Cl40.0478 (5)0.0428 (4)0.0433 (5)0.0293 (4)0.0193 (4)0.0180 (4)

Geometric parameters (Å, °)

Pd1—Cl22.2987 (8)C7—N21.380 (4)
Pd1—Cl12.2989 (8)C7—C121.394 (4)
Pd2—Cl42.2937 (8)C7—C81.395 (4)
Pd2—Cl32.3170 (8)C8—C91.366 (5)
C1—N11.328 (4)C8—H8A0.9300
C1—C21.368 (4)C9—C101.387 (6)
C1—H1B0.9300C9—H9A0.9300
C2—C31.385 (4)C10—C111.373 (5)
C2—H2B0.9300C10—H10A0.9300
C3—C41.388 (4)C11—C121.388 (4)
C3—C61.458 (4)C11—H11A0.9300
C4—C51.371 (5)C12—N31.386 (4)
C4—H4A0.9300N1—Cl43.207 (3)
C5—N11.336 (4)N1—H1A0.8600
C5—Cl1i3.556 (3)N2—Cl3ii3.165 (2)
C5—H5A0.9300N2—H2A0.8600
C6—N21.330 (3)N3—Cl13.138 (3)
C6—N31.338 (3)N3—H3A0.8600
Cl2—Pd1—Cl2iii180.00 (4)N2—C6—N3108.6 (3)
Cl2—Pd1—Cl189.78 (4)N2—C6—C3125.9 (2)
Cl2iii—Pd1—Cl190.22 (4)N3—C6—C3125.5 (3)
Cl2—Pd1—Cl189.78 (4)N2—C7—C12106.6 (3)
Cl2iii—Pd1—Cl190.22 (4)N2—C7—C8131.9 (3)
Cl1—Pd1—Cl10.00 (4)C12—C7—C8121.5 (3)
Cl2—Pd1—Cl1iii90.22 (4)C9—C8—C7116.0 (3)
Cl2iii—Pd1—Cl1iii89.78 (4)C9—C8—H8A122.0
Cl1—Pd1—Cl1iii180.0C7—C8—H8A122.0
Cl1—Pd1—Cl1iii180.0C8—C9—C10122.4 (3)
Cl4—Pd2—Cl40.00 (7)C8—C9—H9A118.8
Cl4—Pd2—Cl4iv180.0C10—C9—H9A118.8
Cl4—Pd2—Cl4iv180.0C11—C10—C9122.2 (3)
Cl4—Pd2—Cl3iv90.27 (3)C11—C10—H10A118.9
Cl4—Pd2—Cl3iv90.27 (3)C9—C10—H10A118.9
Cl4iv—Pd2—Cl3iv89.73 (3)C10—C11—C12116.1 (3)
Cl4—Pd2—Cl389.73 (3)C10—C11—H11A122.0
Cl4—Pd2—Cl389.73 (3)C12—C11—H11A122.0
Cl4iv—Pd2—Cl390.27 (3)N3—C12—C11132.4 (3)
Cl3iv—Pd2—Cl3180.0N3—C12—C7105.9 (3)
N1—C1—C2120.2 (3)C11—C12—C7121.7 (3)
N1—C1—H1B119.9C1—N1—C5122.5 (3)
C2—C1—H1B119.9C1—N1—Cl485.01 (19)
C1—C2—C3119.5 (3)C5—N1—Cl4151.2 (2)
C1—C2—H2B120.3C1—N1—H1A118.7
C3—C2—H2B120.3C5—N1—H1A118.7
C2—C3—C4118.6 (3)C6—N2—C7109.5 (2)
C2—C3—C6119.9 (3)C6—N2—Cl3ii134.59 (18)
C4—C3—C6121.5 (3)C7—N2—Cl3ii115.88 (18)
C5—C4—C3119.9 (3)C6—N2—H2A125.2
C5—C4—H4A120.0C7—N2—H2A125.2
C3—C4—H4A120.0C6—N3—C12109.4 (2)
N1—C5—C4119.3 (3)C6—N3—Cl1130.00 (19)
N1—C5—Cl1i129.9 (2)C12—N3—Cl1120.44 (18)
C4—C5—Cl1i110.8 (2)C6—N3—H3A125.3
N1—C5—H5A120.4C12—N3—H3A125.3
C4—C5—H5A120.4

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

Hydrogen-bond geometry (Å, °)

D—H···AD—HH···AD···AD—H···A
N1—H1A···Cl40.862.553.207 (3)134
N2—H2A···Cl3ii0.862.323.165 (2)167
N3—H3A···Cl10.862.283.138 (3)172
C5—H5A···Cl1i0.932.643.556 (3)167

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

Footnotes

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: BT2834).

References

  • Alcade, E., Dinares, I., Perez-Garia, L. & Roca, T. (1992). Synthesis, pp. 295–398.
  • Brandenburg, K. & Putz, H. (2006). DIAMOND Crystal Impact GbR, Bonn, Germany.
  • Chen, L. J., He, X., Xia, C. K., Zhang, Q. Z., Chen, J. T., Yang, W. B. & Lu, C. Z. (2006). Cryst. Growth Des.9, 2076–2085.
  • Huang, X.-C., Zeng, M.-H. & Ng, S. W. (2004). Acta Cryst. E60, o939–o940.
  • Rigaku (2002). CrystalClear Rigaku Corporation, Tokyo, Japan.
  • Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. [PubMed]
  • Wang, Z. Y., Wilson, S. R., Foxman, B. M. & Lin, W. B. (1999). Cryst. Eng.2, 91–100.

Articles from Acta Crystallographica Section E: Structure Reports Online are provided here courtesy of International Union of Crystallography