catena-Poly[[[tetra­quazinc(II)]-μ-2,5-dihydroxy­benzene-1,4-diacetato-κ2O1:O4] dihydrate]

Wang, L.; Zhang, H.; Yue, L.; Zhang, Z.

doi:10.1107/S1600536808035514

metal-organic compounds

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Volume 64| Part 12| December 2008| Page m1505

doi:10.1107/S1600536808035514

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catena-Poly[[[tetraquazinc(II)]-μ-2,5-dihydroxybenzene-1,4-diacetato-κ²O¹:O⁴] dihydrate]

Liang Wang,^a ^* Hongwei Zhang,^a Lin Yue ^b and Zhaohui Zhang ^a

^aDepartment of Environmental Engineering, Polytechnic Tianjin University, Tianjin 300160, People's Republic of China, and ^bTianjin Tianle International Engineering Consulting Co, Tianjin 300203, People's Republic of China
^*Correspondence e-mail: mashi7822@163.com

(Received 4 September 2008; accepted 30 October 2008; online 8 November 2008)

The title compound, {[Zn(C₁₀H₈O₆)(H₂O)₄]·2H₂O}_n, is a one-dimensional coordination polymer with 2,5-dihydroxybenzene-1,4-diacetate acting as bridging ligand. The zigzag chains, extending parallel to [011], are further packed into a three-dimensional network by hydrogen bonds.

Related literature

For related structures, see Ren et al. (2008 ); Cano et al. (1997 ); Sun et al. (2001 ); Zhao et al. (2004 ).

Experimental

Crystal data

[Zn(C₁₀H₈O₆)(H₂O)₄]·2H₂O
M_r = 397.63
Monoclinic, P 2₁ /c
a = 11.122 (2) Å
b = 7.5176 (15) Å
c = 8.6417 (17) Å
β = 95.12 (3)°
V = 719.7 (2) Å³
Z = 2
Mo Kα radiation
μ = 1.77 mm⁻¹
T = 113 (2) K
0.32 × 0.24 × 0.10 mm

Data collection

Rigaku Saturn diffractometer
Absorption correction: multi-scan (CrystalStructure; Rigaku/MSC, 2005 ) T_min = 0.601, T_max = 0.843
6863 measured reflections
1833 independent reflections
1405 reflections with I > 2σ(I)
R_int = 0.041

Refinement

R[F² > 2σ(F²)] = 0.032
wR(F²) = 0.117
S = 1.17
1833 reflections
125 parameters
9 restraints
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.60 e Å⁻³
Δρ_min = −0.66 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O3—H3⋯O6ⁱ	0.84	1.92	2.725 (3)	160
O4—H4A⋯O2ⁱⁱ	0.857 (10)	1.823 (15)	2.616 (3)	153 (3)
O4—H4A⋯O1ⁱⁱ	0.857 (10)	2.45 (3)	3.011 (3)	123 (3)
O4—H4B⋯O6ⁱⁱⁱ	0.859 (10)	1.925 (10)	2.783 (3)	176 (3)
O5—H5A⋯O3^iv	0.853 (10)	2.000 (15)	2.828 (3)	164 (3)
O5—H5B⋯O4ⁱⁱⁱ	0.855 (10)	1.956 (15)	2.787 (3)	164 (3)
O6—H6A⋯O2^v	0.836 (10)	2.11 (3)	2.781 (3)	137 (3)
O6—H6B⋯O1	0.843 (10)	1.908 (15)	2.721 (3)	162 (3)
Symmetry codes: (i) x, y+1, z; (ii) -x+1, -y+1, -z+1; (iii) $[x, -y+{\script{1\over 2}}, z-{\script{1\over 2}}]$ ; (iv) $[x, -y+{\script{3\over 2}}, z-{\script{1\over 2}}]$ ; (v) $[x, -y+{\script{3\over 2}}, z+{\script{1\over 2}}]$ .

Data collection: CrystalStructure (Rigaku/MSC, 2005); cell refinement: CrystalStructure; data reduction: CrystalStructure; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 (Farrugia, 1997 ); software used to prepare material for publication: CrystalStructure.

Supporting information

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536808035514/bq2094sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536808035514/bq2094Isup2.hkl

checkCIF report

Comment top

Rigid carboxylato ligands, such as benzene-carboxylic acid, pyridine-carboxylic acid, etc. have been widely utilized to synthesize coordination polymers because they can link metal ions via one carboxyl group or via the aroma rings, leading plentiful varieties of structures (Cano et al., 1997; Sun et al., 2001; Zhao, et al., 2004). In contrast, flexible aroma-carboxylic acid and their complexes are less studied comparing to the rigid ones. (Ren et al., 2008)

In this contribution, a flexible ligand, 2,5-dihydroxy-p-benzenediacetic acid (H₂dba), was selected to construct coordination polymer, and the title complex was obtained under solvothermal conditions.

The Zn(II) ion in the title compound is coordinated by two oxygen atoms from dba anions in the apical sites and four water molecules in the equatorial plane (Fig. 1). The Zn(II) ions are linked through dba dianion forming one-dimensional chain (Fig. 2). Furthermore, the chains are packed into three-dimensional supermolecular moiety by O—H···O H-bonds (Fig. 3).

Related literature top

For related structures, see Ren et al. (2008); Cano et al. (1997); Sun et al. (2001); Zhao et al. (2004).

Experimental top

A mixture of Zn(Ac)₂2H₂O (0.5 mmol, 109.8 mg), H₂dba (0.5 mmol, 133.0 mg), 10 ml THF and 10 ml water was put into a 25 ml acid digestion bomb and heated at 80°C for three days. After cooling to room temperature, the title compound (56% yield based on Zn(II) salt) was obtained. Elemental analysis (%) for the title compound C₁₀H₂₀ZnO₁₂: found: C, 29.94; H, 4.96; N, 0. Calc.: C, 30.20; H, 5.07; N, 0.

Computing details top

Data collection: CrystalStructure (Rigaku/MSC, 2005); cell refinement: CrystalStructure (Rigaku/MSC, 2005); data reduction: CrystalStructure (Rigaku/MSC, 2005); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 (Farrugia, 1997); software used to prepare material for publication: CrystalStructure (Rigaku/MSC, 2005).

Figures top

	Fig. 1. The molecular structure of the title compound with 30% probability displacement ellipsoids. Symmetry code: A - x, -y + 2 - z.
	Fig. 2. One-dimensional chain structure of the title compound. H atoms and lattice water molecules are omitted for clarity. Symmetry code: (A) x, y, z; (B) - x, -y + 2 - z; (C) 1 - x, 1 - y, -z.
	Fig. 3. The packing diagram of the title compound.

catena-Poly[[[tetraquazinc(II)]-µ-2,5-dihydroxybenzene-1,4-diacetato- κ²O¹:O⁴] dihydrate] top

Crystal data top

[Zn(C₁₀H₈O₆)(H₂O)₄]·2H₂O	F(000) = 412
M_r = 397.63	D_x = 1.835 Mg m⁻³
Monoclinic, P2₁/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P2ybc	Cell parameters from 1803 reflections
a = 11.122 (2) Å	θ = 2.9–28.6°
b = 7.5176 (15) Å	µ = 1.77 mm⁻¹
c = 8.6417 (17) Å	T = 113 K
β = 95.12 (3)°	Prism, colorless
V = 719.7 (2) Å³	0.32 × 0.24 × 0.10 mm
Z = 2

Data collection top

Rigaku Saturn diffractometer	1833 independent reflections
Radiation source: rotating anode	1405 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.041
ω scans	θ_max = 28.6°, θ_min = 1.8°
Absorption correction: multi-scan (CrystalStructure; Rigaku/MSC, 2005)	h = −14→14
T_min = 0.601, T_max = 0.843	k = −10→10
6863 measured reflections	l = −10→11

Refinement top

Refinement on F²	9 restraints
Least-squares matrix: full	H atoms treated by a mixture of independent and constrained refinement
R[F² > 2σ(F²)] = 0.032	w = 1/[σ²(F_o²) + (0.0565P)² + 0.7652P] where P = (F_o² + 2F_c²)/3
wR(F²) = 0.117	(Δ/σ)_max < 0.001
S = 1.17	Δρ_max = 0.60 e Å⁻³
1833 reflections	Δρ_min = −0.66 e Å⁻³
125 parameters

Crystal data top

[Zn(C₁₀H₈O₆)(H₂O)₄]·2H₂O	V = 719.7 (2) Å³
M_r = 397.63	Z = 2
Monoclinic, P2₁/c	Mo Kα radiation
a = 11.122 (2) Å	µ = 1.77 mm⁻¹
b = 7.5176 (15) Å	T = 113 K
c = 8.6417 (17) Å	0.32 × 0.24 × 0.10 mm
β = 95.12 (3)°

Data collection top

Rigaku Saturn diffractometer	1833 independent reflections
Absorption correction: multi-scan (CrystalStructure; Rigaku/MSC, 2005)	1405 reflections with I > 2σ(I)
T_min = 0.601, T_max = 0.843	R_int = 0.041
6863 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.032	9 restraints
wR(F²) = 0.117	H atoms treated by a mixture of independent and constrained refinement
S = 1.17	Δρ_max = 0.60 e Å⁻³
1833 reflections	Δρ_min = −0.66 e Å⁻³
125 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
Zn1	0.5000	0.5000	0.5000	0.00908 (16)
O1	0.33235 (19)	0.5544 (3)	0.5773 (2)	0.0106 (4)
O2	0.30469 (19)	0.8254 (3)	0.4764 (3)	0.0142 (5)
O3	0.17185 (19)	1.0259 (3)	0.7503 (3)	0.0124 (5)
H3	0.1832	1.1332	0.7746	0.019*
O4	0.4629 (2)	0.2263 (3)	0.5260 (3)	0.0121 (4)
H4A	0.5325 (13)	0.207 (5)	0.494 (4)	0.018*
H4B	0.4037 (18)	0.197 (5)	0.460 (3)	0.018*
O5	0.4263 (2)	0.5039 (3)	0.2703 (3)	0.0138 (4)
H5A	0.3500 (11)	0.517 (4)	0.268 (4)	0.021*
H5B	0.449 (3)	0.426 (4)	0.207 (4)	0.021*
C1	0.2689 (3)	0.6913 (4)	0.5470 (3)	0.0103 (6)
C2	0.1445 (3)	0.6927 (4)	0.6029 (4)	0.0107 (6)
H2A	0.1014	0.5838	0.5647	0.013*
H2B	0.1525	0.6879	0.7178	0.013*
C3	0.0690 (2)	0.8511 (4)	0.5524 (3)	0.0090 (6)
C4	−0.0186 (3)	0.8388 (4)	0.4269 (3)	0.0103 (6)
H4	−0.0321	0.7277	0.3758	0.012*
C5	0.0863 (2)	1.0146 (4)	0.6249 (3)	0.0095 (5)
O6	0.2650 (2)	0.3550 (3)	0.8178 (3)	0.0133 (4)
H6A	0.246 (3)	0.426 (4)	0.886 (3)	0.020*
H6B	0.286 (3)	0.395 (4)	0.733 (2)	0.020*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Zn1	0.0073 (2)	0.0100 (3)	0.0101 (3)	0.00122 (18)	0.00169 (16)	0.00064 (19)
O1	0.0082 (10)	0.0111 (10)	0.0125 (10)	0.0037 (8)	0.0015 (8)	0.0024 (8)
O2	0.0097 (10)	0.0127 (10)	0.0204 (12)	0.0011 (8)	0.0035 (9)	0.0034 (9)
O3	0.0108 (10)	0.0131 (11)	0.0125 (11)	−0.0002 (8)	−0.0035 (8)	−0.0011 (8)
O4	0.0086 (9)	0.0104 (10)	0.0177 (11)	0.0004 (8)	0.0032 (8)	0.0010 (8)
O5	0.0111 (10)	0.0182 (11)	0.0117 (11)	0.0018 (9)	−0.0007 (8)	−0.0026 (9)
C1	0.0089 (13)	0.0116 (14)	0.0104 (14)	0.0005 (11)	−0.0001 (11)	−0.0042 (11)
C2	0.0080 (13)	0.0126 (14)	0.0117 (14)	0.0043 (10)	0.0023 (11)	0.0046 (11)
C3	0.0049 (12)	0.0095 (13)	0.0132 (14)	0.0020 (10)	0.0043 (10)	0.0031 (11)
C4	0.0079 (12)	0.0156 (14)	0.0080 (14)	0.0006 (11)	0.0039 (10)	−0.0018 (11)
C5	0.0048 (11)	0.0159 (14)	0.0082 (13)	0.0023 (11)	0.0027 (9)	0.0011 (11)
O6	0.0159 (11)	0.0119 (11)	0.0123 (11)	−0.0003 (8)	0.0028 (9)	0.0001 (8)

Geometric parameters (Å, º) top

Zn1—O1	2.077 (2)	O5—H5B	0.855 (10)
Zn1—O1ⁱ	2.077 (2)	C1—C2	1.506 (4)
Zn1—O5ⁱ	2.080 (2)	C2—C3	1.500 (4)
Zn1—O5	2.080 (2)	C2—H2A	0.9900
Zn1—O4	2.115 (2)	C2—H2B	0.9900
Zn1—O4ⁱ	2.115 (2)	C3—C5	1.384 (4)
O1—C1	1.262 (3)	C3—C4	1.395 (4)
O2—C1	1.261 (4)	C4—C5ⁱⁱ	1.387 (4)
O3—C5	1.379 (3)	C4—H4	0.9500
O3—H3	0.8400	C5—C4ⁱⁱ	1.387 (4)
O4—H4A	0.857 (10)	O6—H6A	0.836 (10)
O4—H4B	0.859 (10)	O6—H6B	0.843 (10)
O5—H5A	0.853 (10)

O1—Zn1—O1ⁱ	180.0	Zn1—O5—H5B	119 (2)
O1—Zn1—O5ⁱ	89.12 (9)	H5A—O5—H5B	114.9 (18)
O1ⁱ—Zn1—O5ⁱ	90.88 (9)	O2—C1—O1	123.9 (3)
O1—Zn1—O5	90.88 (9)	O2—C1—C2	119.2 (3)
O1ⁱ—Zn1—O5	89.12 (9)	O1—C1—C2	116.8 (3)
O5ⁱ—Zn1—O5	180.0	C3—C2—C1	114.8 (2)
O1—Zn1—O4	88.16 (8)	C3—C2—H2A	108.6
O1ⁱ—Zn1—O4	91.84 (8)	C1—C2—H2A	108.6
O5ⁱ—Zn1—O4	87.08 (8)	C3—C2—H2B	108.6
O5—Zn1—O4	92.92 (9)	C1—C2—H2B	108.6
O1—Zn1—O4ⁱ	91.84 (8)	H2A—C2—H2B	107.6
O1ⁱ—Zn1—O4ⁱ	88.16 (8)	C5—C3—C4	118.1 (3)
O5ⁱ—Zn1—O4ⁱ	92.92 (9)	C5—C3—C2	121.4 (3)
O5—Zn1—O4ⁱ	87.08 (8)	C4—C3—C2	120.5 (3)
O4—Zn1—O4ⁱ	180.0	C5ⁱⁱ—C4—C3	121.3 (3)
C1—O1—Zn1	126.52 (19)	C5ⁱⁱ—C4—H4	119.4
C5—O3—H3	109.5	C3—C4—H4	119.4
Zn1—O4—H4A	86 (3)	O3—C5—C3	117.9 (3)
Zn1—O4—H4B	109 (3)	O3—C5—C4ⁱⁱ	121.4 (3)
H4A—O4—H4B	113.9 (17)	C3—C5—C4ⁱⁱ	120.7 (3)
Zn1—O5—H5A	109 (3)	H6A—O6—H6B	119.8 (19)

O5ⁱ—Zn1—O1—C1	118.5 (2)	C1—C2—C3—C5	−77.9 (4)
O5—Zn1—O1—C1	−61.5 (2)	C1—C2—C3—C4	100.0 (3)
O4—Zn1—O1—C1	−154.4 (2)	C5—C3—C4—C5ⁱⁱ	0.2 (5)
O4ⁱ—Zn1—O1—C1	25.6 (2)	C2—C3—C4—C5ⁱⁱ	−177.7 (3)
Zn1—O1—C1—O2	−7.4 (4)	C4—C3—C5—O3	179.1 (3)
Zn1—O1—C1—C2	173.89 (19)	C2—C3—C5—O3	−2.9 (4)
O2—C1—C2—C3	6.2 (4)	C4—C3—C5—C4ⁱⁱ	−0.2 (5)
O1—C1—C2—C3	−175.0 (3)	C2—C3—C5—C4ⁱⁱ	177.7 (3)

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

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O3—H3···O6ⁱⁱⁱ	0.84	1.92	2.725 (3)	160
O4—H4A···O2ⁱ	0.86 (1)	1.82 (2)	2.616 (3)	153 (3)
O4—H4A···O1ⁱ	0.86 (1)	2.45 (3)	3.011 (3)	123 (3)
O4—H4B···O6^iv	0.86 (1)	1.93 (1)	2.783 (3)	176 (3)
O5—H5A···O3^v	0.85 (1)	2.00 (2)	2.828 (3)	164 (3)
O5—H5B···O4^iv	0.86 (1)	1.96 (2)	2.787 (3)	164 (3)
O6—H6A···O2^vi	0.84 (1)	2.11 (3)	2.781 (3)	137 (3)
O6—H6B···O1	0.84 (1)	1.91 (2)	2.721 (3)	162 (3)

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

Experimental details

Crystal data
Chemical formula	[Zn(C₁₀H₈O₆)(H₂O)₄]·2H₂O
M_r	397.63
Crystal system, space group	Monoclinic, P2₁/c
Temperature (K)	113
a, b, c (Å)	11.122 (2), 7.5176 (15), 8.6417 (17)
β (°)	95.12 (3)
V (Å³)	719.7 (2)
Z	2
Radiation type	Mo Kα
µ (mm⁻¹)	1.77
Crystal size (mm)	0.32 × 0.24 × 0.10

Data collection
Diffractometer	Rigaku Saturn diffractometer
Absorption correction	Multi-scan (CrystalStructure; Rigaku/MSC, 2005)
T_min, T_max	0.601, 0.843
No. of measured, independent and observed [I > 2σ(I)] reflections	6863, 1833, 1405
R_int	0.041
(sin θ/λ)_max (Å⁻¹)	0.674

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.032, 0.117, 1.17
No. of reflections	1833
No. of parameters	125
No. of restraints	9
H-atom treatment	H atoms treated by a mixture of independent and constrained refinement
Δρ_max, Δρ_min (e Å⁻³)	0.60, −0.66

Computer programs: CrystalStructure (Rigaku/MSC, 2005), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), ORTEP-3 (Farrugia, 1997).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O3—H3···O6ⁱ	0.84	1.92	2.725 (3)	160.1
O4—H4A···O2ⁱⁱ	0.857 (10)	1.823 (15)	2.616 (3)	153 (3)
O4—H4A···O1ⁱⁱ	0.857 (10)	2.45 (3)	3.011 (3)	123 (3)
O4—H4B···O6ⁱⁱⁱ	0.859 (10)	1.925 (10)	2.783 (3)	176 (3)
O5—H5A···O3^iv	0.853 (10)	2.000 (15)	2.828 (3)	164 (3)
O5—H5B···O4ⁱⁱⁱ	0.855 (10)	1.956 (15)	2.787 (3)	164 (3)
O6—H6A···O2^v	0.836 (10)	2.11 (3)	2.781 (3)	137 (3)
O6—H6B···O1	0.843 (10)	1.908 (15)	2.721 (3)	162 (3)

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

Acknowledgements

This work was supported by the National Natural Science Foundation of China (grant No. 50578108) and the Sci and Tec Innovation Foundation of Tianjin (No. 06FZZDSH00900).

References

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