Retracted: Poly[aqua­(μ₄-benzene-1,3-dicarboxyl­ato-κ⁴O:O′:O′′:O′′′)bis­(imidazole-κN)palladium(II)]

In the title compound, [Pd(C₈H₄O₄)(C₃H₄N₂)₂(H₂O)]_n, two monodendate imidazole ligands are bonded to the Pd^II atom, and individual units are linked into chains by 1,3-benzene­dicarboxyl­ate anions. The Pd^II atom is seven-coordinated by two N atoms from two imidazole ligands, four O atoms from two independent 1,3-benzene­dicarboxyl­ate anions and one water mol­ecule, exhibiting a distorted penta­gonal–bipyramidal coordination environment. One of the carboxyl­ate O atoms at the base of the pyramid is bonded only very loosely, with a Pd—O distance of 2.771 (2) Å [cf. 2.312 (2)–2.488 (3) Å for the other Pd—O distances]. N—H...O and O—H...O hydrogen-bonding inter­actions link parallel chains together.

Key indicators

• Single-crystal X-ray study
• T = 293 K
• Mean [sigma](C-C) = 0.005 Å
• R factor = 0.031
• wR factor = 0.071
• Data-to-parameter ratio = 14.3

checkCIF/PLATON results

No syntax errors found



Alert level C
PLAT220_ALERT_2_C Large Non-Solvent    C     Ueq(max)/Ueq(min) ...       2.80 Ratio
PLAT242_ALERT_2_C Check Low       Ueq as Compared to Neighbors for         N3

Alert level G
PLAT199_ALERT_1_G Check the Reported _cell_measurement_temperature        293 K
PLAT200_ALERT_1_G Check the Reported _diffrn_ambient_temperature .        293 K
PLAT794_ALERT_5_G Check Predicted Bond Valency for Pd1         (2)       1.35
PLAT860_ALERT_3_G Note: Number of Least-Squares Restraints .......          4

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

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

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S1. Comment

In recent years, carboxylic acids have been widely used as polydentate ligands, which can coordinate to transition or rare earth ions yielding complexes with interesting properties that are useful in materials science (Church & Halvorson, 1959; Chung et al., 1971) and in biological systems (Okabe & Oya, 2000; Serre et al., 2005; Pocker & Fong, 1980; Scapin et al., 1997). Herein, we report the synthesis and X-ray crystal structure analysis of the title compound, poly[aqua (benzene-1,3-dicarboxylato) bis(imidazole) palladium(II)].

The molecular structure of the title compound is shown in Fig. 1. Pd(II) is seven-coordianted with two N atoms from two imidazole ligands, four O atoms from two independent 1,3-benzene dicarboxylate, and one water molecule. The palladium ion exhibits a distorted pentagonal bipyramidal coordination environment with one of the imidazole ligands and the water molecule being located in the two apical positions, and the N and O atoms of the remaining imidazole and the carboxylate ions in the basal plane. One of the carboxylate ions is coordinated to the Pd(II) ion in an asymmetric fashion with the Pd(1)—O(3) bond being with 2.771 (2) Å much longer than the other Pd—O bonding distances (2.312 (2) to 2.488 (3) Å). The 1,3-benzene dicarboxylate ions bridge neigboring Pd(II) ion to gives rise to one-dimensional zigzag chains (Fig. 2). N—H···O and O—H···O hydrogen bonding interactions connect the parallel chains with each other stabilize the structure (see the hydrogen-bond geometry table for numerical values and Figure 3 for a packing diagram showing the H-bond interactions).

Related literature

For related literature, see: Church & Halvorson (1959); Chung et al. (1971); Okabe & Oya (2000); Serre et al. (2005); Pocker & Fong (1980); Scapin et al. (1997).

S2. Experimental

A mixture of palladium acetate (0.5 mmol), imidazole (1.0 mmol), benzene-1,3-dicarboxylic acid (0.5 mmol), H₂O (8 ml) and ethanol (8 ml) in a 25 ml Teflon-lined stainless steel autoclave was kept at 413 K for three days. Colorless crystals were obtained after cooling to room temperature with a yield of 27%. Anal. Calc. for C₁₄H₁₄N₄O₅Pd: C 39.56, H 3.30, N 13.19%; Found: C 39.51, H 3.27, N 13.17%.

S3. Refinement

O—H and N—H hydrogen atoms were located in difference density maps and were refined with distance restraints of d(O—H) = 0.82 (2) Å, d(N—H) = 0.88 (2) Å. All other H atoms were placed in calculated positions with a C—H bond distance of 0.93 Å. U_iso(H) for the water H atoms was set to 1.5U_eq, all others to 1.2U_eq of the respective carrier atom.

Computing details

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

Figures

	Fig. 1. A view of the structure of (I), showing 30% probability displacement ellipsoids.
	Fig. 2. Chains of the title compound along the [010] direction.
	Fig. 3. Packing diagram, viewed along the [010] direction. Dashed lines indicate hydrogen bonds, hydrogen atoms themselves are omitted for clarity.

Poly[aqua(µ₄-benzene-1,3-dicarboxylato-κ⁴O:O':O'':O''') bis(imidazole-κN)palladium(II)]

Crystal data

[Pd(C8H4O4)(C3H4N2)2(H2O)]	F(000) = 848
Mr = 424.69	Dx = 1.684 Mg m^−3
Monoclinic, P21/n	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2yn	Cell parameters from 3516 reflections
a = 8.5814 (17) Å	θ = 1.7–27.0°
b = 19.426 (4) Å	µ = 1.14 mm^−1
c = 10.118 (2) Å	T = 293 K
β = 96.62 (3)°	Cube, colourless
V = 1675.5 (6) Å^3	0.43 × 0.28 × 0.22 mm
Z = 4

Data collection

Bruker APEXII CCD area-detector diffractometer	3280 independent reflections
Radiation source: fine-focus sealed tube	2523 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.031
φ and ω scans	θmax = 26.0°, θmin = 2.3°
Absorption correction: multi-scan (SADABS; Bruker, 2001)	h = −10→9
Tmin = 0.640, Tmax = 0.788	k = −23→11
8842 measured reflections	l = −12→12

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)] = 0.031	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.071	H atoms treated by a mixture of independent and constrained refinement
S = 1.00	w = 1/[σ^2(Fo^2) + (0.0336P)^2] where P = (Fo^2 + 2Fc^2)/3
3280 reflections	(Δ/σ)max = 0.003
229 parameters	Δρmax = 0.40 e Å^−3
4 restraints	Δρmin = −0.63 e Å^−3

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 (Ų)

	x	y	z	Uiso*/Ueq
Pd1	0.37425 (3)	0.126490 (13)	1.00522 (2)	0.03491 (10)
C1	0.4890 (4)	0.2744 (2)	0.8764 (4)	0.0612 (10)
H1	0.4473	0.2630	0.7902	0.073*
C2	0.5780 (5)	0.3305 (2)	0.9103 (5)	0.0653 (11)
H2	0.6097	0.3638	0.8530	0.078*
C3	0.5445 (4)	0.2718 (2)	1.0866 (4)	0.0641 (11)
H3	0.5504	0.2588	1.1755	0.077*
C4	0.0640 (5)	0.2230 (2)	0.9641 (5)	0.0741 (13)
H4	0.1256	0.2624	0.9630	0.089*
C5	−0.0908 (5)	0.2224 (3)	0.9456 (6)	0.1025 (19)
H5	−0.1565	0.2601	0.9272	0.123*
C6	−0.0034 (5)	0.1199 (2)	0.9826 (6)	0.0913 (17)
H6	−0.0009	0.0726	0.9959	0.110*
C7	0.4815 (4)	0.09640 (18)	0.7491 (3)	0.0413 (8)
C8	0.5730 (3)	0.08147 (17)	0.6351 (3)	0.0368 (7)
C9	0.7237 (4)	0.0550 (2)	0.6573 (3)	0.0533 (10)
H9	0.7684	0.0460	0.7438	0.064*
C10	0.8084 (4)	0.0420 (2)	0.5512 (4)	0.0663 (12)
H10	0.9091	0.0238	0.5665	0.080*
C11	0.5089 (4)	0.09436 (17)	0.5050 (3)	0.0388 (7)
H11	0.4072	0.1114	0.4889	0.047*
C12	0.7429 (4)	0.0560 (2)	0.4226 (3)	0.0555 (10)
H12	0.8002	0.0476	0.3516	0.067*
C13	0.5931 (4)	0.08233 (17)	0.3994 (3)	0.0397 (8)
C14	0.5215 (5)	0.09758 (19)	0.2596 (3)	0.0505 (9)
N1	0.4694 (3)	0.23673 (16)	0.9882 (3)	0.0532 (8)
N2	0.6116 (4)	0.32854 (18)	1.0435 (4)	0.0638 (9)
H21	0.682 (4)	0.3538 (18)	1.096 (3)	0.077*
N3	0.1206 (3)	0.15876 (16)	0.9847 (3)	0.0482 (7)
N4	−0.1346 (4)	0.1571 (3)	0.9587 (6)	0.1079 (16)
H20	−0.229 (3)	0.140 (3)	0.935 (6)	0.129*
O1	0.2779 (3)	0.01164 (13)	0.9913 (2)	0.0496 (6)
O2	0.5538 (3)	0.09052 (13)	0.8661 (2)	0.0489 (6)
O3	0.3421 (3)	0.11470 (14)	0.7305 (2)	0.0593 (7)
O4	0.3885 (3)	0.12419 (16)	0.2416 (2)	0.0722 (8)
O5	0.5971 (4)	0.08483 (16)	0.1641 (2)	0.0753 (9)
H22	0.296 (6)	−0.006 (2)	0.920 (3)	0.113*
H23	0.327 (5)	−0.013 (2)	1.048 (4)	0.113*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
Pd1	0.02806 (14)	0.04265 (16)	0.03440 (14)	0.00380 (12)	0.00523 (9)	0.00091 (12)
C1	0.055 (2)	0.061 (3)	0.065 (3)	−0.003 (2)	−0.0070 (19)	0.006 (2)
C2	0.054 (2)	0.062 (3)	0.079 (3)	−0.008 (2)	0.004 (2)	0.011 (2)
C3	0.059 (2)	0.074 (3)	0.061 (2)	−0.016 (2)	0.012 (2)	−0.013 (2)
C4	0.046 (2)	0.051 (3)	0.126 (4)	0.010 (2)	0.011 (2)	−0.004 (3)
C5	0.046 (3)	0.066 (3)	0.193 (6)	0.021 (2)	0.003 (3)	−0.021 (4)
C6	0.034 (2)	0.057 (3)	0.181 (5)	0.002 (2)	0.008 (3)	−0.004 (3)
C7	0.044 (2)	0.047 (2)	0.0327 (17)	0.0011 (17)	0.0051 (14)	0.0022 (15)
C8	0.0366 (17)	0.0414 (19)	0.0331 (16)	−0.0007 (15)	0.0074 (13)	0.0008 (14)
C9	0.042 (2)	0.080 (3)	0.0361 (18)	0.010 (2)	−0.0005 (15)	0.0035 (18)
C10	0.044 (2)	0.109 (4)	0.048 (2)	0.018 (2)	0.0117 (17)	0.000 (2)
C11	0.0363 (17)	0.0436 (19)	0.0364 (17)	0.0022 (16)	0.0031 (14)	0.0011 (15)
C12	0.051 (2)	0.080 (3)	0.0386 (19)	0.004 (2)	0.0174 (16)	−0.0040 (19)
C13	0.0437 (19)	0.0415 (19)	0.0339 (17)	−0.0019 (16)	0.0050 (14)	−0.0011 (15)
C14	0.069 (3)	0.048 (2)	0.0343 (19)	−0.003 (2)	0.0053 (18)	−0.0017 (16)
N1	0.0498 (18)	0.0557 (19)	0.0534 (18)	−0.0094 (16)	0.0024 (14)	−0.0037 (16)
N2	0.0489 (19)	0.061 (2)	0.082 (3)	−0.0150 (17)	0.0069 (17)	−0.0165 (19)
N3	0.0309 (15)	0.0496 (18)	0.064 (2)	0.0047 (14)	0.0043 (13)	−0.0022 (15)
N4	0.036 (2)	0.076 (3)	0.210 (5)	0.001 (2)	0.011 (3)	−0.020 (3)
O1	0.0518 (15)	0.0479 (15)	0.0500 (15)	0.0053 (12)	0.0090 (12)	0.0011 (12)
O2	0.0502 (14)	0.0645 (16)	0.0324 (12)	0.0089 (13)	0.0065 (10)	0.0026 (11)
O3	0.0444 (14)	0.089 (2)	0.0459 (14)	0.0201 (14)	0.0101 (11)	0.0048 (13)
O4	0.0713 (19)	0.103 (2)	0.0404 (14)	0.0198 (18)	−0.0011 (13)	0.0079 (14)
O5	0.109 (2)	0.086 (2)	0.0328 (13)	0.0261 (19)	0.0157 (14)	−0.0034 (14)

Geometric parameters (Å, º)

Pd1—N3	2.252 (3)	C7—O3	1.242 (4)
Pd1—N1	2.305 (3)	C7—O2	1.276 (4)
Pd1—O2	2.311 (2)	C7—C8	1.497 (4)
Pd1—O1	2.378 (3)	C8—C9	1.386 (4)
Pd1—O4^i	2.382 (2)	C8—C11	1.390 (4)
Pd1—O5^i	2.487 (3)	C9—C10	1.387 (4)
C1—C2	1.353 (5)	C9—H9	0.9300
C1—N1	1.374 (5)	C10—C12	1.383 (5)
C1—H1	0.9300	C10—H10	0.9300
C2—N2	1.346 (5)	C11—C13	1.377 (4)
C2—H2	0.9300	C11—H11	0.9300
C3—N1	1.312 (4)	C12—C13	1.379 (4)
C3—N2	1.340 (5)	C12—H12	0.9300
C3—H3	0.9300	C13—C14	1.505 (4)
C4—C5	1.321 (6)	C14—O4	1.247 (4)
C4—N3	1.347 (5)	C14—O5	1.249 (4)
C4—H4	0.9300	N2—H21	0.901 (19)
C5—N4	1.335 (7)	N4—H20	0.88 (2)
C5—H5	0.9300	O1—H22	0.83 (3)
C6—N3	1.302 (5)	O1—H23	0.83 (4)
C6—N4	1.336 (5)	O4—Pd1^ii	2.382 (2)
C6—H6	0.9300	O5—Pd1^ii	2.487 (3)
N3—Pd1—N1	94.67 (11)	C11—C8—C7	120.6 (3)
N3—Pd1—O2	137.15 (9)	C8—C9—C10	120.3 (3)
N1—Pd1—O2	88.21 (10)	C8—C9—H9	119.9
N3—Pd1—O1	85.99 (10)	C10—C9—H9	119.9
N1—Pd1—O1	172.26 (9)	C12—C10—C9	120.0 (3)
O2—Pd1—O1	86.09 (9)	C12—C10—H10	120.0
N3—Pd1—O4^i	92.00 (10)	C9—C10—H10	120.0
N1—Pd1—O4^i	96.59 (11)	C13—C11—C8	121.2 (3)
O2—Pd1—O4^i	130.19 (9)	C13—C11—H11	119.4
O1—Pd1—O4^i	91.10 (9)	C8—C11—H11	119.4
N3—Pd1—O5^i	144.39 (9)	C13—C12—C10	120.2 (3)
N1—Pd1—O5^i	95.63 (11)	C13—C12—H12	119.9
O2—Pd1—O5^i	77.22 (8)	C10—C12—H12	119.9
O1—Pd1—O5^i	88.23 (10)	C11—C13—C12	119.6 (3)
O4^i—Pd1—O5^i	52.98 (9)	C11—C13—C14	120.1 (3)
C2—C1—N1	109.8 (4)	C12—C13—C14	120.3 (3)
C2—C1—H1	125.1	O4—C14—O5	121.1 (3)
N1—C1—H1	125.1	O4—C14—C13	119.1 (3)
N2—C2—C1	106.3 (4)	O5—C14—C13	119.7 (4)
N2—C2—H2	126.8	C3—N1—C1	104.6 (3)
C1—C2—H2	126.8	C3—N1—Pd1	124.9 (3)
N1—C3—N2	111.8 (4)	C1—N1—Pd1	129.3 (3)
N1—C3—H3	124.1	C3—N2—C2	107.4 (3)
N2—C3—H3	124.1	C3—N2—H21	123 (3)
C5—C4—N3	110.6 (4)	C2—N2—H21	129 (3)
C5—C4—H4	124.7	C6—N3—C4	104.8 (3)
N3—C4—H4	124.7	C6—N3—Pd1	128.3 (3)
C4—C5—N4	106.5 (4)	C4—N3—Pd1	126.8 (3)
C4—C5—H5	126.7	C5—N4—C6	106.9 (4)
N4—C5—H5	126.7	C5—N4—H20	126 (4)
N3—C6—N4	111.1 (4)	C6—N4—H20	125 (4)
N3—C6—H6	124.4	Pd1—O1—H22	110 (4)
N4—C6—H6	124.4	Pd1—O1—H23	111 (4)
O3—C7—O2	121.5 (3)	H22—O1—H23	103 (5)
O3—C7—C8	121.4 (3)	C7—O2—Pd1	104.5 (2)
O2—C7—C8	117.1 (3)	C14—O4—Pd1^ii	95.4 (2)
C9—C8—C11	118.7 (3)	C14—O5—Pd1^ii	90.4 (2)
C9—C8—C7	120.6 (3)

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

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
O1—H22···O5^iii	0.83 (3)	2.02 (3)	2.743 (4)	145 (5)
O1—H23···O2^iv	0.83 (4)	1.97 (4)	2.762 (3)	162 (5)
N2—H21···O3^v	0.90 (2)	1.92 (2)	2.801 (4)	165 (4)
N4—H20···O2^vi	0.88 (2)	2.14 (2)	3.020 (5)	173 (5)

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