Poly[diaqua­(μ-4,4′-bipyridine-κ2N:N′)[μ-2,2′-(p-phenyl­enedi­oxy)diacetato-κ2O:O′]cadmium]

Wang, G.-Y.

doi:10.1107/S1600536811031400

metal-organic compounds

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ISSN: 2056-9890

Volume 67| Part 9| September 2011| Page m1248

doi:10.1107/S1600536811031400

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Poly[diaqua(μ-4,4′-bipyridine-κ²N:N′)[μ-2,2′-(p-phenylenedioxy)diacetato-κ²O:O′]cadmium]

Guang-Yin Wang ^a ^*

^aDepartment of Chemistry, Dezhou University, Dezhou, Shandong 253023, People's Republic of China
^*Correspondence e-mail: dzgywang@126.com

(Received 14 July 2011; accepted 3 August 2011; online 17 August 2011)

In the title compound, [Cd(C₁₀H₈O₆)(C₁₀H₈N₂)(H₂O)₂]_n, the Cd^II ion has inversion symmetry and is coordinated by O atoms from two water molecules and two bridging 2,2′-(μ-p-phenylenedioxy)diacetate ligands and two N atoms from two 4,4′-bipyridine ligands, giving a slightly distorted octahedral geometry. The diacetate and 4,4′-bipyridine ligands also lie across inversion centers. The bridging ligands form layers parallel to (11 $[\overline{1}]$ ), with adjacent layers interconnected via O—H⋯O hydrogen bonds between the coordinated water molecules and the carboxylate O atoms, giving a three-dimensional supramolecular architecture.

Related literature

Benzene-1,4-dioxydiacetic acid is often used to construct coordination polymers owing to the flexibility of the two phenoxyacetate groups, see: Gong et al. (2010 ); Li et al. (2010 ); Zhang & Li (2010 ).

Experimental

Crystal data

[Cd(C₁₀H₈O₆)(C₁₀H₈N₂)(H₂O)₂]
M_r = 528.78
Triclinic, $[P \overline 1]$
a = 5.8612 (6) Å
b = 8.2313 (8) Å
c = 10.8659 (11) Å
α = 105.640 (1)°
β = 97.6785 (12)°
γ = 97.931 (1)°
V = 491.91 (9) Å³
Z = 1
Mo Kα radiation
μ = 1.16 mm⁻¹
T = 296 K
0.21 × 0.11 × 0.04 mm

Data collection

Bruker APEXII CCD area-detector diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2001 ) T_min = 0.789, T_max = 0.956
2533 measured reflections
1691 independent reflections
1667 reflections with I > 2σ(I)
R_int = 0.014

Refinement

R[F² > 2σ(F²)] = 0.027
wR(F²) = 0.067
S = 1.14
1691 reflections
142 parameters
H-atom parameters constrained
Δρ_max = 0.45 e Å⁻³
Δρ_min = −0.39 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O1W—H2W⋯O2ⁱ	0.85	1.81	2.636 (4)	165
O1W—H1W⋯O1ⁱⁱ	0.85	2.05	2.858 (4)	159
Symmetry codes: (i) -x+1, -y+1, -z+1; (ii) -x, -y+1, -z+1.

Data collection: APEX2 (Bruker, 2007 ); cell refinement: SAINT (Bruker, 2007); data reduction: SAINT; program(s) used to solve structure: SIR97 (Altomare et al., 1999 ); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ); molecular graphics: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: WinGX (Farrugia, 1999 ).

Supporting information

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536811031400/zs2132sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536811031400/zs2132Isup2.hkl

checkCIF report

Comment top

Due to the flexibility of the two phenoxyacetate groups, benzene-1,4-dioxydiacetic acid is often used to construct coordination polymers (Zhang & Li, 2010; Gong et al., 2010; Li et al., 2010;). The title coordination polymer [Cd(C₁₀H₈O₆)(C₁₀H₈N₂)(H₂O)₂]_n (I) was obtained under hydrothermal conditions, and its crystal structure is reported here .

The asymmetric unit of (I) is composed of one Cd^II cation lying on a crystallographic inversion centre, half a benzene-1,4-dioxydiacetate anion, half a 4,4'-bipyridine molecule and one water molecule. The Cd^II ion is coordinated by O atoms from two water molecules [Cd—O, 2.313 (3)Å] and two from bridging benzene-1,4-dioxydiacetate ligands [Cd—O, 2.253 (2) Å] and two N atoms from two 4,4'-bipyridine ligands [Cd—N, 2.317 (3) Å], giving a slightly distorted octahedral geometry (Fig. 1). The benzene-1,4-dioxydiacetate and 4,4'-bipyridine ligands also lie across inversion centers, with both bridging the Cd^II cations to form two-dimensional layers parallel to the (1 1 -1) plane (Fig. 2). These layers are further interconnected via O—H···O hydrogen bonds between the coordinated water molecules and the carboxylate O atoms, resulting in a three-dimensional supramolecular architecture (Table 1, Fig. 3).

Related literature top

Experimental top

A mixture of benzene-1,4-dioxydiacetic acid (0.023 g, 0.1 mmol), 4,4'-bipyridine (0.016 g, 0.1 mmol), NaOH (0.008 g, 0.2 mmol) and Cd(NO₃)₂. 4H₂O (0.038 g, 0.1 mmol) in H₂O (7.0 ml) was placed in a 16 ml Teflon-lined stainless steel vessel and heated to 160 °C for 72 h, then cooled to room temperature at a rate of -5 °C/h. Colorless plate crystals are obtained after filtration.

Computing details top

Data collection: APEX2 (Bruker, 2007); cell refinement: SAINT (Bruker, 2007); data reduction: SAINT (Bruker, 2007); program(s) used to solve structure: SIR97 (Altomare et al., 1999); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: WinGX (Farrugia, 1999).

Figures top

	Fig. 1. Anisotropic displacement ellipsoid plot of (I) at the 50% probability level. H atoms are represented by circles of arbitrary size. Symmetry code: (i)-x + 1, -y, -z; (ii)-x, -y + 1, -z; (iii) -x + 1, -y + 1, -z + 1.
	Fig. 2. The two-dimensional layered substructure of (I). H atoms are omitted except for those of the water molecules.
	Fig. 3. The overall packing diagram of (I) showing showing hydrogen-bonding interactions as dashed lines.

Poly[diaqua(µ-4,4'-bipyridine-κ²N:N')[µ-2,2'-(p- phenylenedioxy)diacetato-κ²O:O']cadmium] top

Crystal data top

[Cd(C₁₀H₈O₆)(C₁₀H₈N₂)(H₂O)₂]	Z = 1
M_r = 528.78	F(000) = 266
Triclinic, P1	D_x = 1.785 Mg m⁻³
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 5.8612 (6) Å	Cell parameters from 1861 reflections
b = 8.2313 (8) Å	θ = 2.6–27.8°
c = 10.8659 (11) Å	µ = 1.16 mm⁻¹
α = 105.640 (1)°	T = 296 K
β = 97.6785 (12)°	Plate, colorless
γ = 97.931 (1)°	0.21 × 0.11 × 0.04 mm
V = 491.91 (9) Å³

Data collection top

Bruker APEXII CCD area-detector diffractometer	1691 independent reflections
Radiation source: fine-focus sealed tube	1667 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.014
ϕ and ω scans	θ_max = 25.0°, θ_min = 2.0°
Absorption correction: multi-scan (SADABS; Bruker, 2001)	h = −6→5
T_min = 0.789, T_max = 0.956	k = −9→9
2533 measured reflections	l = −12→12

Refinement top

Refinement on F²	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F² > 2σ(F²)] = 0.027	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.067	H-atom parameters constrained
S = 1.14	w = 1/[σ²(F_o²) + (0.0276P)² + 0.6011P] where P = (F_o² + 2F_c²)/3
1691 reflections	(Δ/σ)_max < 0.001
142 parameters	Δρ_max = 0.45 e Å⁻³
0 restraints	Δρ_min = −0.39 e Å⁻³

Crystal data top

[Cd(C₁₀H₈O₆)(C₁₀H₈N₂)(H₂O)₂]	γ = 97.931 (1)°
M_r = 528.78	V = 491.91 (9) Å³
Triclinic, P1	Z = 1
a = 5.8612 (6) Å	Mo Kα radiation
b = 8.2313 (8) Å	µ = 1.16 mm⁻¹
c = 10.8659 (11) Å	T = 296 K
α = 105.640 (1)°	0.21 × 0.11 × 0.04 mm
β = 97.6785 (12)°

Data collection top

Bruker APEXII CCD area-detector diffractometer	1691 independent reflections
Absorption correction: multi-scan (SADABS; Bruker, 2001)	1667 reflections with I > 2σ(I)
T_min = 0.789, T_max = 0.956	R_int = 0.014
2533 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.027	0 restraints
wR(F²) = 0.067	H-atom parameters constrained
S = 1.14	Δρ_max = 0.45 e Å⁻³
1691 reflections	Δρ_min = −0.39 e Å⁻³
142 parameters

Special details top

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

	x	y	z	U_iso*/U_eq
C1	0.3288 (6)	0.2750 (4)	0.2007 (3)	0.0314 (7)
H1	0.2097	0.3389	0.2098	0.038*
C2	0.3250 (6)	0.1600 (4)	0.0818 (3)	0.0313 (7)
H2	0.2047	0.1479	0.0130	0.038*
C3	0.4983 (5)	0.0624 (4)	0.0637 (3)	0.0221 (6)
C4	0.6685 (6)	0.0859 (5)	0.1715 (3)	0.0371 (8)
H4	0.7881	0.0223	0.1656	0.044*
C5	0.6607 (6)	0.2037 (5)	0.2877 (3)	0.0386 (8)
H5	0.7771	0.2169	0.3586	0.046*
C6	0.3586 (6)	0.7739 (4)	0.3662 (3)	0.0294 (7)
C7	0.1802 (6)	0.8591 (4)	0.3031 (3)	0.0358 (8)
H7A	0.1348	0.9458	0.3706	0.043*
H7B	0.2542	0.9168	0.2478	0.043*
C8	−0.1959 (6)	0.4972 (5)	0.0564 (3)	0.0334 (8)
H8	−0.3285	0.4941	0.0948	0.040*
C9	−0.0019 (6)	0.6241 (4)	0.1162 (3)	0.0296 (7)
C10	0.1962 (6)	0.6247 (4)	0.0590 (3)	0.0336 (8)
H10	0.3294	0.7076	0.0986	0.040*
N1	0.4958 (5)	0.2990 (3)	0.3034 (2)	0.0271 (6)
O1	0.2781 (4)	0.6403 (3)	0.3942 (2)	0.0314 (5)
O2	0.5658 (5)	0.8448 (3)	0.3879 (3)	0.0511 (7)
O3	−0.0252 (4)	0.7435 (3)	0.2275 (2)	0.0362 (5)
O1W	0.1584 (4)	0.3373 (3)	0.5183 (2)	0.0385 (6)
H1W	0.0509	0.3664	0.5598	0.046*
H2W	0.2264	0.2728	0.5543	0.046*
Cd1	0.5000	0.5000	0.5000	0.02535 (13)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
C1	0.0336 (18)	0.0297 (17)	0.0304 (17)	0.0152 (14)	0.0023 (14)	0.0051 (14)
C2	0.0350 (19)	0.0312 (17)	0.0244 (16)	0.0121 (14)	−0.0063 (13)	0.0049 (13)
C3	0.0242 (16)	0.0216 (14)	0.0195 (15)	0.0021 (12)	0.0033 (12)	0.0057 (12)
C4	0.0302 (18)	0.050 (2)	0.0268 (17)	0.0192 (16)	−0.0002 (14)	−0.0001 (15)
C5	0.035 (2)	0.053 (2)	0.0215 (16)	0.0162 (17)	−0.0027 (14)	0.0008 (15)
C6	0.0330 (19)	0.0304 (17)	0.0256 (16)	0.0132 (15)	0.0093 (14)	0.0038 (13)
C7	0.042 (2)	0.0319 (18)	0.0371 (19)	0.0124 (16)	0.0072 (16)	0.0128 (15)
C8	0.0250 (17)	0.048 (2)	0.0336 (18)	0.0095 (15)	0.0092 (14)	0.0195 (16)
C9	0.0302 (18)	0.0369 (18)	0.0292 (17)	0.0125 (15)	0.0055 (14)	0.0187 (14)
C10	0.0268 (17)	0.0386 (18)	0.0363 (19)	−0.0002 (14)	0.0025 (14)	0.0170 (15)
N1	0.0279 (14)	0.0280 (13)	0.0237 (13)	0.0062 (11)	0.0038 (11)	0.0043 (11)
O1	0.0348 (13)	0.0325 (12)	0.0306 (12)	0.0111 (10)	0.0048 (10)	0.0136 (10)
O2	0.0339 (15)	0.0488 (16)	0.078 (2)	0.0089 (12)	0.0097 (13)	0.0296 (15)
O3	0.0324 (13)	0.0453 (14)	0.0327 (12)	0.0138 (11)	0.0062 (10)	0.0108 (11)
O1W	0.0268 (13)	0.0500 (15)	0.0409 (14)	0.0076 (11)	0.0066 (10)	0.0164 (12)
Cd1	0.0268 (2)	0.02717 (19)	0.02091 (18)	0.00758 (13)	0.00313 (12)	0.00441 (13)

Geometric parameters (Å, º) top

C1—N1	1.334 (4)	C7—H7B	0.9700
C1—C2	1.376 (5)	C8—C10ⁱⁱ	1.379 (5)
C1—H1	0.9300	C8—C9	1.384 (5)
C2—C3	1.382 (4)	C8—H8	0.9300
C2—H2	0.9300	C9—O3	1.374 (4)
C3—C4	1.385 (4)	C9—C10	1.388 (5)
C3—C3ⁱ	1.489 (6)	C10—C8ⁱⁱ	1.379 (5)
C4—C5	1.379 (5)	C10—H10	0.9300
C4—H4	0.9300	N1—Cd1	2.317 (3)
C5—N1	1.327 (4)	O1—Cd1	2.253 (2)
C5—H5	0.9300	O1W—Cd1	2.313 (3)
C6—O2	1.234 (4)	O1W—H1W	0.8467
C6—O1	1.265 (4)	O1W—H2W	0.8499
C6—C7	1.526 (5)	Cd1—O1ⁱⁱⁱ	2.253 (2)
C7—O3	1.424 (4)	Cd1—O1Wⁱⁱⁱ	2.313 (3)
C7—H7A	0.9700	Cd1—N1ⁱⁱⁱ	2.317 (3)

N1—C1—C2	122.9 (3)	O3—C9—C10	125.2 (3)
N1—C1—H1	118.5	C8—C9—C10	118.7 (3)
C2—C1—H1	118.5	C8ⁱⁱ—C10—C9	120.2 (3)
C1—C2—C3	120.6 (3)	C8ⁱⁱ—C10—H10	119.9
C1—C2—H2	119.7	C9—C10—H10	119.9
C3—C2—H2	119.7	C5—N1—C1	117.0 (3)
C2—C3—C4	116.1 (3)	C5—N1—Cd1	121.5 (2)
C2—C3—C3ⁱ	122.3 (3)	C1—N1—Cd1	121.6 (2)
C4—C3—C3ⁱ	121.6 (3)	C6—O1—Cd1	123.8 (2)
C5—C4—C3	120.0 (3)	C9—O3—C7	117.8 (3)
C5—C4—H4	120.0	Cd1—O1W—H1W	130.3
C3—C4—H4	120.0	Cd1—O1W—H2W	95.3
N1—C5—C4	123.4 (3)	H1W—O1W—H2W	107.2
N1—C5—H5	118.3	O1ⁱⁱⁱ—Cd1—O1	180.000 (1)
C4—C5—H5	118.3	O1ⁱⁱⁱ—Cd1—O1W	91.72 (10)
O2—C6—O1	126.7 (3)	O1—Cd1—O1W	88.28 (10)
O2—C6—C7	116.8 (3)	O1ⁱⁱⁱ—Cd1—O1Wⁱⁱⁱ	88.28 (10)
O1—C6—C7	116.5 (3)	O1—Cd1—O1Wⁱⁱⁱ	91.72 (10)
O3—C7—C6	114.1 (3)	O1W—Cd1—O1Wⁱⁱⁱ	180.0
O3—C7—H7A	108.7	O1ⁱⁱⁱ—Cd1—N1	90.66 (9)
C6—C7—H7A	108.7	O1—Cd1—N1	89.34 (9)
O3—C7—H7B	108.7	O1W—Cd1—N1	88.66 (9)
C6—C7—H7B	108.7	O1Wⁱⁱⁱ—Cd1—N1	91.34 (9)
H7A—C7—H7B	107.6	O1ⁱⁱⁱ—Cd1—N1ⁱⁱⁱ	89.34 (9)
C10ⁱⁱ—C8—C9	121.2 (3)	O1—Cd1—N1ⁱⁱⁱ	90.66 (9)
C10ⁱⁱ—C8—H8	119.4	O1W—Cd1—N1ⁱⁱⁱ	91.34 (9)
C9—C8—H8	119.4	O1Wⁱⁱⁱ—Cd1—N1ⁱⁱⁱ	88.66 (9)
O3—C9—C8	116.2 (3)	N1—Cd1—N1ⁱⁱⁱ	180.000 (1)

N1—C1—C2—C3	0.0 (5)	C7—C6—O1—Cd1	−175.7 (2)
C1—C2—C3—C4	1.1 (5)	C8—C9—O3—C7	170.1 (3)
C1—C2—C3—C3ⁱ	−179.4 (3)	C10—C9—O3—C7	−11.8 (4)
C2—C3—C4—C5	−1.1 (5)	C6—C7—O3—C9	−66.8 (4)
C3ⁱ—C3—C4—C5	179.5 (4)	C6—O1—Cd1—O1W	170.5 (2)
C3—C4—C5—N1	−0.1 (6)	C6—O1—Cd1—O1Wⁱⁱⁱ	−9.5 (2)
O2—C6—C7—O3	152.4 (3)	C6—O1—Cd1—N1	−100.8 (2)
O1—C6—C7—O3	−29.5 (4)	C6—O1—Cd1—N1ⁱⁱⁱ	79.2 (2)
C10ⁱⁱ—C8—C9—O3	177.0 (3)	C5—N1—Cd1—O1ⁱⁱⁱ	−22.8 (3)
C10ⁱⁱ—C8—C9—C10	−1.3 (5)	C1—N1—Cd1—O1ⁱⁱⁱ	157.9 (3)
O3—C9—C10—C8ⁱⁱ	−176.8 (3)	C5—N1—Cd1—O1	157.2 (3)
C8—C9—C10—C8ⁱⁱ	1.3 (5)	C1—N1—Cd1—O1	−22.1 (3)
C4—C5—N1—C1	1.2 (5)	C5—N1—Cd1—O1W	−114.5 (3)
C4—C5—N1—Cd1	−178.2 (3)	C1—N1—Cd1—O1W	66.2 (3)
C2—C1—N1—C5	−1.1 (5)	C5—N1—Cd1—O1Wⁱⁱⁱ	65.5 (3)
C2—C1—N1—Cd1	178.2 (3)	C1—N1—Cd1—O1Wⁱⁱⁱ	−113.8 (3)
O2—C6—O1—Cd1	2.1 (5)

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

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O1W—H2W···O2ⁱⁱⁱ	0.85	1.81	2.636 (4)	165
O1W—H1W···O1^iv	0.85	2.05	2.858 (4)	159

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

Experimental details

Crystal data
Chemical formula	[Cd(C₁₀H₈O₆)(C₁₀H₈N₂)(H₂O)₂]
M_r	528.78
Crystal system, space group	Triclinic, P1
Temperature (K)	296
a, b, c (Å)	5.8612 (6), 8.2313 (8), 10.8659 (11)
α, β, γ (°)	105.640 (1), 97.6785 (12), 97.931 (1)
V (Å³)	491.91 (9)
Z	1
Radiation type	Mo Kα
µ (mm⁻¹)	1.16
Crystal size (mm)	0.21 × 0.11 × 0.04

Data collection
Diffractometer	Bruker APEXII CCD area-detector diffractometer
Absorption correction	Multi-scan (SADABS; Bruker, 2001)
T_min, T_max	0.789, 0.956
No. of measured, independent and observed [I > 2σ(I)] reflections	2533, 1691, 1667
R_int	0.014
(sin θ/λ)_max (Å⁻¹)	0.594

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.027, 0.067, 1.14
No. of reflections	1691
No. of parameters	142
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.45, −0.39

Computer programs: APEX2 (Bruker, 2007), SAINT (Bruker, 2007), SIR97 (Altomare et al., 1999), SHELXL97 (Sheldrick, 2008), SHELXTL (Sheldrick, 2008), WinGX (Farrugia, 1999).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O1W—H2W···O2ⁱ	0.85	1.81	2.636 (4)	165
O1W—H1W···O1ⁱⁱ	0.85	2.05	2.858 (4)	159

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

Acknowledgements

This work was supported financially by the Project of Shandong Province Higher Educational Science and Technology Program (grant No. J11LB56).

References

Altomare, A., Burla, M. C., Camalli, M., Cascarano, G. L., Giacovazzo, C., Guagliardi, A., Moliterni, A. G. G., Polidori, G. & Spagna, R. (1999). J. Appl. Cryst. 32, 115–119. Web of Science CrossRef CAS IUCr Journals Google Scholar
Bruker (2001). SADABS. Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
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