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Acta Crystallogr Sect E Struct Rep Online. 2008 January 1; 64(Pt 1): m133.
Published online 2007 December 6. doi:  10.1107/S1600536807065051
PMCID: PMC2915081

This article has been retractedRetraction in: Acta Crystallogr Sect E Struct Rep Online. 2012 July 01; 68(Pt 7): e14    See also: PMC Retraction Policy

catena-Poly[[bis­(1H-benzimidazole-κN 3)palladium(II)]-μ-benzene-1,4-dicarboxyl­ato-κ2 O 1:O 4]

Abstract

In the title compound, [Pd(C8H4O4)(C7H6N2)2]n, the Pd atom is tetra­coordinated by two carboxyl­ate O atoms from two benzene-1,4-dicarboxyl­ate (bdc) dianions and two N atoms from two benzimidazole ligands, resulting in a slightly distorted tetra­hedral PdO2N2 geometry. The bdc ligand acts as a bridge, linking the Pd atoms into a chain. Inter-chain N—H(...)O hydrogen bonds help to stabilize the crystal structure.

Related literature

For background, see: Okabe & Oya (2000 [triangle]).

An external file that holds a picture, illustration, etc.
Object name is e-64-0m133-scheme1.jpg

Experimental

Crystal data

  • [Pd(C8H4O4)(C7H6N2)2]
  • M r = 506.79
  • Monoclinic, An external file that holds a picture, illustration, etc.
Object name is e-64-0m133-efi4.jpg
  • a = 17.0627 (5) Å
  • b = 7.3612 (10) Å
  • c = 18.0210 (5) Å
  • β = 114.362 (3)°
  • V = 2061.9 (3) Å3
  • Z = 4
  • Mo Kα radiation
  • μ = 0.94 mm−1
  • T = 273 (2) K
  • 0.43 × 0.28 × 0.22 mm

Data collection

  • Bruker APEXII CCD diffractometer
  • Absorption correction: multi-scan (SADABS; Bruker, 2001 [triangle]) T min = 0.689, T max = 0.820
  • 10244 measured reflections
  • 3763 independent reflections
  • 3136 reflections with I > 2σ(I)
  • R int = 0.021

Refinement

  • R[F 2 > 2σ(F 2)] = 0.021
  • wR(F 2) = 0.044
  • S = 1.00
  • 3763 reflections
  • 280 parameters
  • H-atom parameters constrained
  • Δρmax = 0.25 e Å−3
  • Δρmin = −0.30 e Å−3

Data collection: APEX2 (Bruker, 2004 [triangle]); cell refinement: SAINT-Plus (Bruker, 2001 [triangle]); data reduction: SAINT-Plus; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997 [triangle]); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997 [triangle]); molecular graphics: SHELXTL (Bruker, 2001 [triangle]); software used to prepare material for publication: SHELXTL.

Table 1
Selected bond lengths (Å)
Table 2
Hydrogen-bond geometry (Å, °)

Supplementary Material

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536807065051/hb2670sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536807065051/hb2670Isup2.hkl

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

Acknowledgments

The authors thank the Education Department of Shandong Province for research and development projects (J06A55).

supplementary crystallographic information

Comment

Dicarboxylic acids are key components in the synthesis of coordination polymers (e.g. Okabe & Oya, 2000). In this paper, we report the structure of the title compound, (I).

In compound (I) the Pd atom is tetra-coordinated by two oxygen atoms from two benzene-1,4-dicarboxylate (bdc) dianions and two nitrogen atoms from two benzimidazole ligands, resulting in a slightly distorterd tetrahedral PdO4N2 geometry for the metal (Fig. 1, Table 1). Two short Pd···O contacts arise from this arrangement [Pd1···O2 = 2.7015 (15)Å and Pd1···O1i = 2.5324 (14) Å; i = x - 1/2,-y + 5/2,z - 1/2] The bdc acts as a bridge to link Pd atoms into a chain (Fig. 2).

Two N—H···O hydrogen bonds (Table 2) help to link the chains into a three-dimensional structure.

Experimental

A mixture of palladium acetate (1 mmol), benzene-1,4-dicarboxylic acid (1 mmol), benzimidazole (2 mmol), and 8 ml H2O was sealed in a 25 ml autoclave and heated to 413 K for 2 days. On cooling to room temperature, colourless blocks of (I) were obtained with a yield of 12%. Anal. Calc. for C22H16N4O4Pd: C 60.77, H 3.16, N 11.05%; Found: C 60.71, H 3.22, N 47.01%.

Refinement

All H atoms were placed in calculated positions with C—H = 0.93Å and N—H = 0.86Å and refined as riding with Uiso(H) = 1.2Ueq(carrier).

Figures

Fig. 1.
The molecular structure of (I), drawn with 30% probability displacement ellipsoids for the non-hydrogen atoms. The unlabelled O3 atom is at the symmetry position (x - 1/2, -y + 5/2, z - 1/2).
Fig. 2.
Fragment of a one dimensional chain in (I).

Crystal data

[Pd(C8H4O4)(C7H6N2)2]F000 = 1016
Mr = 506.79Dx = 1.633 Mg m3
Monoclinic, P21/nMo Kα radiation λ = 0.71073 Å
Hall symbol: -P 2ynCell parameters from 3823 reflections
a = 17.0627 (5) Åθ = 2.5–25.5º
b = 7.3612 (10) ŵ = 0.94 mm1
c = 18.0210 (5) ÅT = 273 (2) K
β = 114.362 (3)ºBlock, colourless
V = 2061.9 (3) Å30.43 × 0.28 × 0.22 mm
Z = 4

Data collection

Bruker APEXII CCD diffractometer3763 independent reflections
Radiation source: fine-focus sealed tube3136 reflections with I > 2σ(I)
Monochromator: graphiteRint = 0.021
T = 273(2) Kθmax = 25.5º
[var phi] and ω scansθmin = 2.5º
Absorption correction: multi-scan(SADABS; Bruker, 2001)h = −20→18
Tmin = 0.689, Tmax = 0.820k = −8→8
10244 measured reflectionsl = −16→21

Refinement

Refinement on F2Secondary atom site location: difference Fourier map
Least-squares matrix: fullHydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.021H-atom parameters constrained
wR(F2) = 0.044  w = 1/[σ2(Fo2) + (0.0204P)2 + 0.1114P] where P = (Fo2 + 2Fc2)/3
S = 1.00(Δ/σ)max = 0.007
3763 reflectionsΔρmax = 0.25 e Å3
280 parametersΔρmin = −0.30 e Å3
Primary atom site location: structure-invariant direct methodsExtinction correction: none

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
Pd10.386453 (9)0.87505 (2)0.131047 (8)0.03602 (6)
C10.38692 (14)0.4922 (3)0.05522 (12)0.0501 (5)
H10.32730.50280.03200.060*
C20.51274 (14)0.3771 (3)0.08708 (12)0.0465 (5)
C30.51865 (12)0.5488 (3)0.12239 (11)0.0414 (5)
C40.58302 (16)0.2724 (3)0.09742 (14)0.0600 (6)
H40.57810.15950.07270.072*
C50.59695 (13)0.6213 (3)0.17173 (13)0.0514 (5)
H50.60210.73480.19590.062*
C60.66649 (15)0.5167 (4)0.18295 (14)0.0642 (6)
H60.72080.56010.21640.077*
C70.65997 (17)0.3453 (4)0.14617 (15)0.0677 (7)
H70.71000.28030.15560.081*
C80.23606 (14)0.7875 (3)0.18459 (14)0.0558 (6)
H80.19700.78110.13030.067*
C90.35186 (13)0.8107 (3)0.29148 (12)0.0442 (5)
C100.28633 (14)0.7875 (3)0.31634 (13)0.0498 (5)
C110.30073 (17)0.7824 (4)0.39652 (15)0.0698 (7)
H110.25590.76680.41260.084*
C120.43443 (14)0.8292 (3)0.34715 (13)0.0549 (6)
H120.47930.84570.33120.066*
C130.44869 (17)0.8227 (4)0.42700 (15)0.0749 (8)
H130.50470.83340.46650.090*
C140.3826 (2)0.8007 (4)0.45121 (16)0.0843 (8)
H140.39480.79850.50650.101*
C150.49046 (12)1.1428 (3)0.23451 (11)0.0402 (5)
C160.56002 (11)1.2527 (3)0.29649 (11)0.0381 (4)
C170.64130 (13)1.1842 (3)0.32852 (12)0.0508 (5)
H170.65281.07300.31070.061*
C180.54456 (13)1.4201 (3)0.32342 (12)0.0500 (5)
H180.48931.46830.30100.060*
C190.60938 (13)1.5157 (3)0.38254 (12)0.0517 (6)
H190.59801.62740.40010.062*
C200.70605 (13)1.2803 (3)0.38725 (12)0.0512 (5)
H200.76171.23380.40880.061*
C210.68998 (12)1.4463 (3)0.41515 (11)0.0392 (4)
C220.75824 (12)1.5416 (3)0.48470 (11)0.0423 (5)
N10.21398 (12)0.7742 (3)0.24689 (12)0.0596 (5)
H1A0.16270.75960.24360.072*
N20.31782 (11)0.8103 (2)0.20759 (10)0.0477 (4)
N30.42774 (12)0.3463 (2)0.04448 (10)0.0527 (5)
H3A0.40450.25140.01600.063*
N40.43772 (11)0.6190 (2)0.10114 (10)0.0456 (4)
O10.74180 (9)1.6814 (2)0.51415 (9)0.0616 (4)
O20.41604 (8)1.1972 (2)0.20972 (8)0.0517 (4)
O30.83114 (8)1.46812 (19)0.51434 (8)0.0510 (4)
O40.51057 (8)0.99635 (19)0.20976 (8)0.0516 (4)

Atomic displacement parameters (Å2)

U11U22U33U12U13U23
Pd10.02818 (8)0.04723 (9)0.02930 (9)−0.00258 (7)0.00849 (6)0.00106 (6)
C10.0435 (12)0.0563 (13)0.0459 (12)−0.0098 (10)0.0138 (10)−0.0010 (10)
C20.0561 (13)0.0490 (12)0.0371 (11)−0.0015 (11)0.0221 (10)0.0066 (10)
C30.0410 (12)0.0494 (12)0.0360 (11)−0.0018 (9)0.0180 (9)0.0026 (9)
C40.0762 (18)0.0561 (14)0.0552 (14)0.0118 (13)0.0348 (13)0.0061 (11)
C50.0415 (12)0.0627 (13)0.0506 (13)−0.0062 (11)0.0196 (10)−0.0052 (11)
C60.0425 (14)0.0929 (19)0.0581 (15)−0.0005 (13)0.0217 (11)0.0025 (14)
C70.0602 (17)0.090 (2)0.0626 (16)0.0250 (14)0.0351 (14)0.0149 (14)
C80.0415 (13)0.0714 (15)0.0541 (14)−0.0101 (11)0.0194 (11)0.0052 (12)
C90.0449 (12)0.0463 (11)0.0448 (12)0.0012 (9)0.0219 (10)0.0057 (9)
C100.0491 (13)0.0530 (12)0.0538 (14)−0.0008 (10)0.0277 (11)0.0044 (11)
C110.0730 (18)0.0872 (18)0.0654 (17)−0.0066 (15)0.0448 (15)0.0048 (14)
C120.0468 (13)0.0694 (15)0.0496 (13)0.0032 (11)0.0210 (11)0.0093 (11)
C130.0617 (16)0.108 (2)0.0487 (15)−0.0052 (14)0.0164 (13)0.0122 (14)
C140.094 (2)0.115 (2)0.0515 (16)−0.0136 (18)0.0375 (16)0.0058 (15)
C150.0316 (11)0.0570 (13)0.0334 (10)−0.0034 (9)0.0148 (8)0.0020 (9)
C160.0337 (10)0.0493 (12)0.0310 (10)−0.0023 (9)0.0128 (8)−0.0015 (8)
C170.0377 (12)0.0596 (13)0.0492 (13)0.0047 (10)0.0120 (10)−0.0170 (10)
C180.0344 (11)0.0571 (13)0.0470 (12)0.0087 (9)0.0053 (9)−0.0043 (10)
C190.0425 (12)0.0527 (13)0.0475 (13)0.0081 (10)0.0060 (10)−0.0107 (10)
C200.0320 (11)0.0648 (14)0.0487 (13)0.0076 (10)0.0084 (9)−0.0102 (11)
C210.0361 (11)0.0482 (11)0.0311 (10)0.0000 (9)0.0117 (8)−0.0008 (9)
C220.0386 (12)0.0510 (12)0.0335 (11)−0.0001 (10)0.0110 (9)0.0021 (9)
N10.0430 (11)0.0751 (13)0.0693 (13)−0.0076 (10)0.0317 (10)0.0075 (11)
N20.0404 (10)0.0595 (11)0.0452 (10)−0.0043 (8)0.0196 (8)0.0014 (8)
N30.0598 (12)0.0479 (11)0.0458 (10)−0.0114 (9)0.0171 (9)−0.0077 (8)
N40.0412 (10)0.0491 (10)0.0432 (10)−0.0059 (8)0.0141 (8)−0.0053 (8)
O10.0449 (9)0.0736 (10)0.0552 (10)0.0035 (7)0.0097 (7)−0.0251 (8)
O20.0290 (8)0.0759 (10)0.0461 (8)−0.0005 (7)0.0114 (6)−0.0057 (7)
O30.0378 (8)0.0546 (9)0.0441 (8)0.0077 (7)0.0002 (6)−0.0024 (7)
O40.0390 (8)0.0575 (9)0.0528 (9)−0.0046 (7)0.0134 (7)−0.0161 (7)

Geometric parameters (Å, °)

Pd1—O42.1945 (13)C11—C141.343 (3)
Pd1—N22.1987 (17)C11—H110.9300
Pd1—N42.2355 (17)C12—C131.358 (3)
Pd1—O3i2.2382 (13)C12—H120.9300
Pd1—O1i2.5324 (14)C13—C141.377 (4)
C1—N41.310 (2)C13—H130.9300
C1—N31.337 (3)C14—H140.9300
C1—H10.9300C15—O21.227 (2)
C2—N31.351 (3)C15—O41.267 (2)
C2—C41.372 (3)C15—C161.489 (3)
C2—C31.400 (3)C16—C171.360 (3)
C3—C51.371 (3)C16—C181.389 (3)
C3—N41.373 (2)C17—C201.370 (3)
C4—C71.354 (3)C17—H170.9300
C4—H40.9300C18—C191.372 (3)
C5—C61.358 (3)C18—H180.9300
C5—H50.9300C19—C211.353 (3)
C6—C71.408 (3)C19—H190.9300
C6—H60.9300C20—C211.391 (3)
C7—H70.9300C20—H200.9300
C8—N21.292 (2)C21—C221.488 (3)
C8—N11.327 (3)C22—O11.242 (2)
C8—H80.9300C22—O31.256 (2)
C9—C121.358 (3)N1—H1A0.8600
C9—C101.376 (3)N3—H3A0.8600
C9—N21.378 (2)O1—Pd1ii2.5324 (14)
C10—N11.351 (3)O3—Pd1ii2.2382 (13)
C10—C111.363 (3)
O4—Pd1—N2107.72 (6)C14—C13—H13119.1
O4—Pd1—N497.45 (6)C11—C14—C13121.3 (2)
N2—Pd1—N4109.34 (6)C11—C14—H14119.4
O4—Pd1—O3i108.54 (5)C13—C14—H14119.4
N2—Pd1—O3i125.04 (6)O2—C15—O4122.67 (18)
N4—Pd1—O3i105.28 (6)O2—C15—C16118.73 (19)
N4—C1—N3114.5 (2)O4—C15—C16118.60 (17)
N4—C1—H1122.7C17—C16—C18119.19 (18)
N3—C1—H1122.7C17—C16—C15118.35 (18)
N3—C2—C4131.0 (2)C18—C16—C15122.46 (17)
N3—C2—C3105.61 (18)C16—C17—C20119.53 (19)
C4—C2—C3123.4 (2)C16—C17—H17120.2
C5—C3—N4129.27 (19)C20—C17—H17120.2
C5—C3—C2121.0 (2)C19—C18—C16121.20 (18)
N4—C3—C2109.73 (17)C19—C18—H18119.4
C7—C4—C2115.1 (2)C16—C18—H18119.4
C7—C4—H4122.4C21—C19—C18119.55 (19)
C2—C4—H4122.4C21—C19—H19120.2
C6—C5—C3115.7 (2)C18—C19—H19120.2
C6—C5—H5122.2C17—C20—C21121.10 (18)
C3—C5—H5122.2C17—C20—H20119.4
C5—C6—C7122.9 (2)C21—C20—H20119.4
C5—C6—H6118.5C19—C21—C20119.41 (18)
C7—C6—H6118.5C19—C21—C22119.34 (18)
C4—C7—C6121.9 (2)C20—C21—C22121.06 (17)
C4—C7—H7119.1O1—C22—O3122.26 (18)
C6—C7—H7119.1O1—C22—C21120.94 (18)
N2—C8—N1112.6 (2)O3—C22—C21116.68 (18)
N2—C8—H8123.7C8—N1—C10107.97 (19)
N1—C8—H8123.7C8—N1—H1A126.0
C12—C9—C10120.5 (2)C10—N1—H1A126.0
C12—C9—N2130.5 (2)C8—N2—C9105.25 (18)
C10—C9—N2109.00 (18)C8—N2—Pd1127.66 (15)
N1—C10—C11132.6 (2)C9—N2—Pd1126.54 (13)
N1—C10—C9105.20 (19)C1—N3—C2106.50 (17)
C11—C10—C9122.2 (2)C1—N3—H3A126.7
C14—C11—C10117.0 (2)C2—N3—H3A126.7
C14—C11—H11121.5C1—N4—C3103.61 (17)
C10—C11—H11121.5C1—N4—Pd1122.03 (15)
C9—C12—C13117.2 (2)C3—N4—Pd1134.34 (13)
C9—C12—H12121.4C22—O1—Pd1ii84.55 (11)
C13—C12—H12121.4C22—O3—Pd1ii97.89 (12)
C12—C13—C14121.9 (2)C15—O4—Pd1104.15 (12)
C12—C13—H13119.1

Symmetry codes: (i) x−1/2, −y+5/2, z−1/2; (ii) x+1/2, −y+5/2, z+1/2.

Hydrogen-bond geometry (Å, °)

D—H···AD—HH···AD···AD—H···A
N3—H3A···O3iii0.862.042.762 (2)142
N1—H1A···O2iv0.861.912.699 (2)152

Symmetry codes: (iii) x−1/2, −y+3/2, z−1/2; (iv) −x+1/2, y−1/2, −z+1/2.

Footnotes

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: HB2670).

References

  • Bruker (2001). SADABS, SAINT-Plus and SHELXTL Bruker AXS Inc., Madison, Wisconsin, USA.
  • Bruker (2004). APEX2 Bruker AXS Inc., Madison, Wisconsin, USA.
  • Okabe, N. & Oya, N. (2000). Acta Cryst. C56, 1416–1417. [PubMed]
  • Sheldrick, G. M. (1997). SHELXS97 and SHELXL97 University of Göttingen, Germany.

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