Tetra-aqua-bis[(1-carboxyl-atomethyl-1,3-benzimidazol-3-ium-3-yl)acetato-κO]palladium(II) dihydrate.

In the title compound, [Pd(C(11)H(9)N(2)O(4))(2)(H(2)O)(4)]·2H(2)O, the palladium(II) cation lies on an inversion centre and is hexa-coordinated by two carboxyl-ate O atoms from two (1-carboxyl-atomethyl-1,3-benzimidazol-3-ium-3-yl)acetate ligands and four water mol-ecules, with a slightly distorted octa-hedral geometry. O-H⋯O hydrogen bonds link the mol-ecules together.

Related literature

For uses of carboxylic acids in materials science, see: Church & Halvorson (1959 ▶). For uses in biological systems, see: Chung et al. (1971 ▶); Okabe & Oya (2000 ▶); Serre et al. (2005 ▶); Pocker & Fong (1980 ▶); Scapin et al. (1997 ▶); Kim et al. (2001 ▶).

Experimental

Crystal data

[Pd(C11H9N2O4)2(H2O)4]·2H2O

M = 680.90

Monoclinic,

a = 5.4702 (10) Å

b = 11.794 (2) Å

c = 20.886 (3) Å

β = 95.13 (3)°

V = 1342.1 (4) Å3

Z = 2

Mo Kα radiation

μ = 0.77 mm−1

T = 293 (2) K

0.43 × 0.28 × 0.22 mm

Data collection

Bruker APEXII CCD area-detector diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2004 ▶) T min = 0.733, T max = 0.849

7075 measured reflections

2425 independent reflections

1958 reflections with I > 2σ(I)

R int = 0.032

Refinement

R[F 2 > 2σ(F 2)] = 0.028

wR(F 2) = 0.072

S = 1.00

2425 reflections

205 parameters

9 restraints

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.24 e Å−3

Δρmin = −0.49 e Å−3

Data collection: APEX2 (Bruker, 2004 ▶); cell refinement: SAINT-Plus (Bruker, 2004 ▶); data reduction: SAINT-Plus; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: SHELXTL (Sheldrick, 2008 ▶); software used to prepare material for publication: SHELXTL.

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536808016097/cf2196sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536808016097/cf2196Isup2.hkl

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

[Pd(C11H9N2O4)2(H2O)4]·2H2O	F000 = 696
Mr = 680.90	Dx = 1.685 Mg m−3
Monoclinic, P21/n	Mo Kα radiation λ = 0.71073 Å
Hall symbol: -P 2yn	Cell parameters from 2425 reflections
a = 5.4702 (10) Å	θ = 2.0–25.2º
b = 11.794 (2) Å	µ = 0.77 mm−1
c = 20.886 (3) Å	T = 293 (2) K
β = 95.13 (3)º	Block, colorless
V = 1342.1 (4) Å3	0.43 × 0.28 × 0.22 mm
Z = 2

Bruker APEXII CCD area-detector diffractometer	2425 independent reflections
Radiation source: fine-focus sealed tube	1958 reflections with I > 2σ(I)
Monochromator: graphite	Rint = 0.032
T = 293(2) K	θmax = 25.2º
φ and ω scans	θmin = 2.0º
Absorption correction: multi-scan(SADABS; Bruker, 2004)	h = −6→6
Tmin = 0.733, Tmax = 0.849	k = −13→14
7075 measured reflections	l = −24→13

Refinement on F2	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.028	H atoms treated by a mixture of independent and constrained refinement
wR(F2) = 0.072	w = 1/[σ2(Fo2) + (0.042P)2] where P = (Fo2 + 2Fc2)/3
S = 1.00	(Δ/σ)max = 0.005
2425 reflections	Δρmax = 0.24 e Å−3
205 parameters	Δρmin = −0.49 e Å−3
9 restraints	Extinction correction: none
Primary atom site location: structure-invariant direct methods

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.

	x	y	z	Uiso*/Ueq
Pd1	0.5000	1.0000	0.0000	0.02449 (11)
C1	0.7711 (5)	1.0484 (2)	0.14648 (12)	0.0299 (6)
C2	0.5544 (5)	0.9924 (2)	0.17543 (12)	0.0326 (6)
H2A	0.4065	1.0354	0.1631	0.039*
H2B	0.5316	0.9166	0.1578	0.039*
C3	0.4539 (5)	1.0371 (2)	0.28620 (12)	0.0294 (6)
H3	0.3237	1.0858	0.2745	0.035*
C4	0.7676 (4)	0.9208 (2)	0.28035 (12)	0.0279 (6)
C5	0.9568 (5)	0.8536 (2)	0.26202 (14)	0.0365 (7)
H5	0.9834	0.8433	0.2190	0.044*
C6	1.1029 (6)	0.8030 (3)	0.31070 (17)	0.0480 (8)
H6	1.2346	0.7586	0.3006	0.058*
C7	1.0587 (6)	0.8166 (3)	0.37470 (17)	0.0540 (9)
H7	1.1595	0.7793	0.4062	0.065*
C8	0.8726 (6)	0.8828 (3)	0.39307 (15)	0.0449 (7)
H8	0.8444	0.8916	0.4360	0.054*
C9	0.7282 (5)	0.9361 (2)	0.34427 (12)	0.0299 (6)
C11	0.4355 (5)	1.0558 (3)	0.40327 (13)	0.0369 (7)
H11A	0.4276	0.9955	0.4346	0.044*
H11B	0.2696	1.0831	0.3923	0.044*
C12	0.5910 (5)	1.1527 (2)	0.43369 (13)	0.0347 (6)
H1W	0.545 (5)	0.681 (2)	0.2365 (7)	0.042*
H2W	0.571 (4)	0.693 (2)	0.1719 (9)	0.042*
H3W	0.160 (5)	1.1619 (14)	0.0196 (13)	0.042*
H4W	0.074 (4)	1.078 (2)	0.0568 (12)	0.042*
H5W	0.503 (3)	0.7896 (18)	0.0589 (13)	0.042*
H6W	0.270 (3)	0.799 (2)	0.0290 (13)	0.042*
N1	0.5889 (4)	0.98516 (17)	0.24523 (11)	0.0290 (5)
N2	0.5306 (4)	1.01001 (17)	0.34575 (11)	0.0301 (5)
O1	0.1897 (3)	1.09974 (17)	0.03739 (10)	0.0394 (5)
O2	0.3926 (4)	0.83292 (17)	0.04423 (10)	0.0451 (5)
O3	0.7682 (3)	1.03890 (18)	0.08641 (9)	0.0384 (5)
O4	0.9339 (4)	1.09448 (18)	0.18150 (9)	0.0460 (5)
O5	0.7726 (4)	1.1842 (2)	0.40763 (11)	0.0650 (7)
O6	0.5172 (3)	1.19231 (18)	0.48365 (9)	0.0439 (5)
O7	0.4821 (4)	0.7010 (2)	0.20114 (10)	0.0485 (5)

	U11	U22	U33	U12	U13	U23
Pd1	0.02495 (17)	0.02873 (18)	0.01952 (16)	−0.00361 (11)	0.00047 (11)	0.00121 (11)
C1	0.0280 (14)	0.0368 (15)	0.0252 (15)	0.0003 (12)	0.0035 (11)	0.0001 (12)
C2	0.0323 (15)	0.0429 (17)	0.0225 (14)	−0.0058 (12)	0.0013 (12)	−0.0005 (11)
C3	0.0301 (14)	0.0302 (14)	0.0285 (15)	−0.0017 (11)	0.0057 (12)	−0.0005 (11)
C4	0.0297 (14)	0.0259 (14)	0.0280 (14)	−0.0057 (11)	0.0025 (11)	−0.0017 (11)
C5	0.0348 (15)	0.0316 (16)	0.0433 (18)	−0.0014 (12)	0.0053 (13)	−0.0082 (13)
C6	0.0394 (17)	0.0315 (17)	0.072 (2)	0.0073 (13)	−0.0003 (16)	−0.0058 (15)
C7	0.055 (2)	0.042 (2)	0.061 (2)	0.0064 (16)	−0.0148 (17)	0.0110 (16)
C8	0.0555 (19)	0.0411 (18)	0.0369 (17)	−0.0030 (15)	−0.0020 (14)	0.0067 (13)
C9	0.0336 (15)	0.0261 (15)	0.0295 (15)	−0.0037 (12)	0.0007 (11)	0.0001 (11)
C11	0.0397 (16)	0.0461 (18)	0.0264 (15)	−0.0038 (14)	0.0115 (12)	−0.0088 (13)
C12	0.0360 (15)	0.0362 (16)	0.0322 (16)	0.0023 (12)	0.0049 (12)	−0.0056 (12)
N1	0.0282 (12)	0.0365 (14)	0.0227 (12)	−0.0006 (9)	0.0046 (9)	0.0024 (9)
N2	0.0342 (13)	0.0327 (13)	0.0239 (12)	−0.0027 (9)	0.0058 (10)	−0.0037 (9)
O1	0.0368 (11)	0.0391 (12)	0.0445 (13)	−0.0023 (9)	0.0158 (9)	0.0021 (9)
O2	0.0349 (12)	0.0429 (13)	0.0558 (14)	−0.0055 (9)	−0.0058 (10)	0.0164 (10)
O3	0.0353 (11)	0.0585 (13)	0.0212 (11)	−0.0095 (9)	0.0023 (8)	−0.0004 (9)
O4	0.0425 (12)	0.0675 (15)	0.0279 (11)	−0.0240 (10)	0.0021 (9)	−0.0049 (9)
O5	0.0650 (16)	0.0750 (17)	0.0596 (15)	−0.0360 (13)	0.0314 (13)	−0.0339 (13)
O6	0.0475 (13)	0.0510 (14)	0.0339 (11)	0.0038 (9)	0.0067 (9)	−0.0152 (9)
O7	0.0458 (13)	0.0635 (15)	0.0366 (13)	0.0001 (11)	0.0067 (10)	0.0083 (11)

Pd1—O1	2.2608 (19)	C6—C7	1.389 (4)
Pd1—O1i	2.2608 (19)	C6—H6	0.930
Pd1—O3	2.2687 (19)	C7—C8	1.364 (5)
Pd1—O3i	2.2687 (19)	C7—H7	0.930
Pd1—O2i	2.276 (2)	C8—C9	1.383 (4)
Pd1—O2	2.276 (2)	C8—H8	0.930
C1—O4	1.227 (3)	C9—N2	1.392 (3)
C1—O3	1.258 (3)	C11—N2	1.455 (3)
C1—C2	1.529 (4)	C11—C12	1.528 (4)
C2—N1	1.456 (3)	C11—H11A	0.970
C2—H2A	0.970	C11—H11B	0.970
C2—H2B	0.970	C12—O5	1.232 (3)
C3—N2	1.316 (4)	C12—O6	1.243 (3)
C3—N1	1.329 (3)	O1—H3W	0.832 (10)
C3—H3	0.930	O1—H4W	0.823 (10)
C4—C9	1.383 (3)	O2—H5W	0.828 (10)
C4—C5	1.384 (4)	O2—H6W	0.824 (10)
C4—N1	1.394 (3)	O7—H1W	0.822 (10)
C5—C6	1.373 (4)	O7—H2W	0.821 (10)
C5—H5	0.930
O1—Pd1—O1i	180.00 (9)	C5—C6—H6	119.2
O1—Pd1—O3	94.14 (7)	C7—C6—H6	119.2
O1i—Pd1—O3	85.86 (8)	C8—C7—C6	122.4 (3)
O1—Pd1—O3i	85.86 (8)	C8—C7—H7	118.8
O1i—Pd1—O3i	94.14 (7)	C6—C7—H7	118.8
O3—Pd1—O3i	180.0	C7—C8—C9	116.3 (3)
O1—Pd1—O2i	85.34 (7)	C7—C8—H8	121.8
O1i—Pd1—O2i	94.66 (7)	C9—C8—H8	121.8
O3—Pd1—O2i	88.61 (7)	C8—C9—C4	121.6 (3)
O3i—Pd1—O2i	91.39 (7)	C8—C9—N2	131.4 (3)
O1—Pd1—O2	94.66 (7)	C4—C9—N2	106.9 (2)
O1i—Pd1—O2	85.34 (7)	N2—C11—C12	113.2 (2)
O3—Pd1—O2	91.39 (7)	N2—C11—H11A	108.9
O3i—Pd1—O2	88.61 (7)	C12—C11—H11A	108.9
O2i—Pd1—O2	180.00 (10)	N2—C11—H11B	108.9
O4—C1—O3	125.3 (2)	C12—C11—H11B	108.9
O4—C1—C2	120.2 (2)	H11A—C11—H11B	107.7
O3—C1—C2	114.5 (2)	O5—C12—O6	126.3 (3)
N1—C2—C1	112.7 (2)	O5—C12—C11	118.9 (2)
N1—C2—H2A	109.1	O6—C12—C11	114.8 (2)
C1—C2—H2A	109.1	C3—N1—C4	108.4 (2)
N1—C2—H2B	109.1	C3—N1—C2	126.0 (2)
C1—C2—H2B	109.1	C4—N1—C2	125.5 (2)
H2A—C2—H2B	107.8	C3—N2—C9	108.3 (2)
N2—C3—N1	110.3 (2)	C3—N2—C11	125.6 (2)
N2—C3—H3	124.8	C9—N2—C11	125.9 (2)
N1—C3—H3	124.8	Pd1—O1—H3W	115.2 (18)
C9—C4—C5	121.8 (2)	Pd1—O1—H4W	130.4 (18)
C9—C4—N1	106.0 (2)	H3W—O1—H4W	111 (2)
C5—C4—N1	132.3 (2)	Pd1—O2—H5W	118.6 (19)
C6—C5—C4	116.4 (3)	Pd1—O2—H6W	120.1 (19)
C6—C5—H5	121.8	H5W—O2—H6W	112 (2)
C4—C5—H5	121.8	C1—O3—Pd1	139.53 (17)
C5—C6—C7	121.5 (3)	H1W—O7—H2W	114 (2)

D—H···A	D—H	H···A	D···A	D—H···A
O7—H1W···O4ii	0.822 (10)	1.985 (14)	2.756 (3)	156 (3)
O7—H2W···O5ii	0.821 (10)	1.937 (10)	2.747 (3)	169 (3)

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O7—H1W⋯O4i	0.822 (10)	1.985 (14)	2.756 (3)	156 (3)
O7—H2W⋯O5i	0.821 (10)	1.937 (10)	2.747 (3)	169 (3)

Symmetry code: (i) .