catena-Poly[[[tetra­aqua­zinc(II)]-μ-4,4′-bipyridine-κ2N:N′] naphthalene-1,5-disulfonate]

Lin, J.; Cai, W.-L.

doi:10.1107/S1600536809032127

metal-organic compounds

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ISSN: 2056-9890

Volume 65| Part 9| September 2009| Page m1088

doi:10.1107/S1600536809032127

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catena-Poly[[[tetraaquazinc(II)]-μ-4,4′-bipyridine-κ²N:N′] naphthalene-1,5-disulfonate]

Jing Lin ^a and Wen-Lian Cai ^b ^*

^aDepartment of Pharmacy, Xiamen University, Xiamen, Fujian 363105, People's Republic of China, and ^bDepartment of Chemistry and Environmental Science, Zhangzhou Normal University, Zhangzhou, Fujian 363000, People's Republic of China
^*Correspondence e-mail: ghx919@yahoo.com.cn

(Received 12 August 2009; accepted 13 August 2009; online 19 August 2009)

In the title complex, {[Zn(C₁₀H₈N₂)(H₂O)₄](C₁₀H₆O₆S₂)}_n, the [Zn(4,4′-bipy)(H₂O)₄]²⁺ (4,4′-bipy is 4,4′-bipyridine) cations are linked into linear chains along [001] by the 4,4′-bipy ligands. The Zn^II ion exhibits a slightly distorted octahedral coordination geometry in which the four water molecules are in the equatorial positions. The anions are hydrogen bonded to the polycationic chains by O—H⋯O hydrogen bonds, forming a three-dimensional network. The Zn^II ion, 4,4′-bipy ligand and anion lie on special positions of 2/m site symmetry.

Related literature

For the design, preparation and applications of metal-organic hybrid materials, see: Batten & Robson (1998 ); Hagrman et al. (1999 ); Cui et al. (2003 ). For the structural and photoluminescent properties of d¹⁰ metal (such as Zn) complexes, see: Li et al. (2003 ); Sattarzadeh et al. (2009 ). 4,4′-Bipyridine can be used to assembly many transition metal coordination polymers through covalent or hydrogen bonds, see: Yaghi & Li (1995 , 1996 ).

Experimental

Crystal data

[Zn(C₁₀H₈N₂)(H₂O)₄](C₁₀H₆O₆S₂)
M_r = 579.89
Monoclinic, C 2/m
a = 14.584 (3) Å
b = 7.3948 (15) Å
c = 11.380 (2) Å
β = 108.38 (3)°
V = 1164.7 (4) Å³
Z = 2
Mo Kα radiation
μ = 1.29 mm⁻¹
T = 293 K
0.38 × 0.29 × 0.19 mm

Data collection

Siemens SMART CCD area-detector diffractometer
Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ) T_min = 0.658, T_max = 0.794
5711 measured reflections
1421 independent reflections
1302 reflections with I > 2σ(I)
R_int = 0.033

Refinement

R[F² > 2σ(F²)] = 0.034
wR(F²) = 0.107
S = 1.03
1421 reflections
107 parameters
15 restraints
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.46 e Å⁻³
Δρ_min = −0.52 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O1w—H1wa⋯O3	0.85 (2)	1.92 (2)	2.763 (3)	175 (3)
O1w—H1wb⋯O2ⁱ	0.83 (2)	1.95 (2)	2.768 (3)	166 (3)
Symmetry code: (i) $[-x+{\script{3\over 2}}, y+{\script{1\over 2}}, -z+1]$ .

Data collection: SMART (Siemens, 1994 ); cell refinement: SAINT (Siemens, 1994); data reduction: SAINT program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ); molecular graphics: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXTL.

Supporting information

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536809032127/ng2626sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536809032127/ng2626Isup2.hkl

checkCIF report

Comment top

The design and preparation of metal-organic hybrid materials have been studied widely during the past decade owing to their intriguing structures and potential practical applications. (Hagrman et al., 1999; Batten & Robson, 1998; Cui et al., 2003). It has been demonstrated that many d¹⁰ metal(such as Zn) complexes present intriguing structural and photoluminescent properties (Li et al.,2003; Sattarzadeh et al., 2009). On the other hand, bridged ligand,4,4'-bipyridine, can be efficiently used to assembly many interesting transition metal coordination polymers through covalent or hydrogen bonds (Yaghi & Li, 1995, 1996). In this work, we use 4,4'-bpy, 1, 5-naphthalenedisulphonic acid(NDS) and Zn(OAc)₂ to synthesize a novel 1-D chain polymer through hydrothermal synthesis.

Complex (I) consists of one-dimensional chains formed by 4,4'- bipy ligands through connecting Zn atoms,uncoordinated NDS^2- anions, as shown in Fig. 1. The [Zn(4,4'-bipy)(H₂O)₄]²⁺ cation is located on a twofold rotation axis that passes through atoms Zn1, N1 and C3. In the cation, the Zn1 atom exhibits slightly distorted octahedral coordination geometry, completed by four O atoms from four water molecules in the equatorial positions and two N donors from two 4,4'-bipy ligands in the apical positions. These Zn–O and Zn–N distances are 2.127 (2) and 2.131 (2) Å, respectively. The 4,4'-bipy ligand acts as bis-monodentate linkers and bridge adjacent Zn centers with the Zn···Zn separation of 11.380 (2)Å into an infinite one-dimensional chain.

In complex (I), the NDS^2- anions are not involved in coordination but hydrogen-bondedto the [Zn(4,4'-bipy)(H₂O)₄]²⁺ cations through the sulfonate oxygen atoms and the coordinated oxygen atoms, forming a three-dimensional hydrogen-bonding network, as shown in Fig. 2.

Related literature top

For the design, preparation and applications of metal-organic hybrid materials, see: Batten & Robson (1998); Hagrman et al. (1999); Cui et al. (2003). For the structural and photoluminescent properties of d¹⁰ metal (such as Zn) complexes, see: Li et al. (2003); Sattarzadeh et al. (2009). 4,4'-Bipyridine can be used to assembly many transition metal coordination polymers through covalent or hydrogen bonds, see: Yaghi & Li (1995, 1996).

Experimental top

The hydrothermal reaction of Zn(OAc)₂.2H₂O (0.5707 g,2.6 mmol), 1,5-Naphthalenedisulphonic acid(0.5405 g, 1.5 mmol), 4,4'-bipyridine(0.4681 g, 3.0 mmol) and water (15 ml) was carried out at 443 K for 3 d. After cooling to room temperature at 5 K h^-1, the colorless block crystalline complex, (I), was isolated in 49% yield (based on Zn).

Computing details top

Data collection: SMART (Siemens, 1994); cell refinement: SAINT (Siemens, 1994); data reduction: SAINT (Siemens, 1994); 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 (Sheldrick, 2008).

Figures top

	Fig. 1. View of the structure of compound (I), showing the atom-labelling scheme. Displacement ellipsoids are drawn at the 35% probability level; H atoms have been omitted for clarity.
	Fig. 2. View of the 3D hydrogen-bonded network in the packing of the title compound. The packing is viewed along the b axis; O-H···O interactions are shown as dashed lines.

catena-Poly[[[tetraaquazinc(II)]-µ-4,4'-bipyridine- κ²N:N'] naphthalene-1,5-disulfonate] top

Crystal data top

[Zn(C₁₀H₈N₂)(H₂O)₄](C₁₀H₆O₆S₂)	F(000) = 596
M_r = 579.89	D_x = 1.654 Mg m⁻³
Monoclinic, C2/m	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -C 2y	Cell parameters from 5711 reflections
a = 14.584 (3) Å	θ = 3.1–27.4°
b = 7.3948 (15) Å	µ = 1.29 mm⁻¹
c = 11.380 (2) Å	T = 293 K
β = 108.38 (3)°	Block, colorless
V = 1164.7 (4) Å³	0.38 × 0.29 × 0.19 mm
Z = 2

Data collection top

Siemens SMART CCD area-detector diffractometer	1421 independent reflections
Radiation source: fine-focus sealed tube	1302 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.033
ω scans	θ_max = 27.4°, θ_min = 3.1°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −18→18
T_min = 0.658, T_max = 0.794	k = −9→9
5711 measured reflections	l = −13→14

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)] = 0.034	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.107	H atoms treated by a mixture of independent and constrained refinement
S = 1.03	w = 1/[σ²(F_o²) + (0.0663P)² + 1.4457P] where P = (F_o² + 2F_c²)/3
1421 reflections	(Δ/σ)_max = 0.001
107 parameters	Δρ_max = 0.46 e Å⁻³
15 restraints	Δρ_min = −0.52 e Å⁻³

Crystal data top

[Zn(C₁₀H₈N₂)(H₂O)₄](C₁₀H₆O₆S₂)	V = 1164.7 (4) Å³
M_r = 579.89	Z = 2
Monoclinic, C2/m	Mo Kα radiation
a = 14.584 (3) Å	µ = 1.29 mm⁻¹
b = 7.3948 (15) Å	T = 293 K
c = 11.380 (2) Å	0.38 × 0.29 × 0.19 mm
β = 108.38 (3)°

Data collection top

Siemens SMART CCD area-detector diffractometer	1421 independent reflections
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	1302 reflections with I > 2σ(I)
T_min = 0.658, T_max = 0.794	R_int = 0.033
5711 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.034	15 restraints
wR(F²) = 0.107	H atoms treated by a mixture of independent and constrained refinement
S = 1.03	Δρ_max = 0.46 e Å⁻³
1421 reflections	Δρ_min = −0.52 e Å⁻³
107 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	0.0328 (2)
S1	0.84039 (6)	0.5000	0.70300 (8)	0.0323 (3)
O1W	0.60582 (14)	0.7084 (3)	0.54834 (19)	0.0443 (5)
H1WA	0.6631 (16)	0.698 (5)	0.596 (2)	0.053*
H1WB	0.605 (2)	0.790 (4)	0.498 (3)	0.053*
O2	0.8672 (2)	0.5000	0.5896 (2)	0.0451 (7)
O3	0.78840 (14)	0.6629 (3)	0.71577 (18)	0.0425 (5)
C1	0.5820 (3)	0.5000	0.7822 (4)	0.0669 (15)
H1A	0.6403	0.5000	0.7651	0.080*
C2	0.5848 (3)	0.5000	0.9042 (4)	0.0647 (14)
H2A	0.6440	0.5000	0.9667	0.078*
C3	0.4997 (3)	0.5000	0.9346 (3)	0.0324 (8)
C4	0.4162 (3)	0.5000	0.8359 (3)	0.0364 (8)
H4A	0.3568	0.5000	0.8501	0.044*
C5	0.4189 (3)	0.5000	0.7155 (3)	0.0337 (8)
H5A	0.3607	0.5000	0.6511	0.040*
C6	0.8693 (3)	0.5000	0.9887 (4)	0.0580 (14)
H6A	0.8090	0.5000	0.9283	0.070*
C7	0.9543 (2)	0.5000	0.9528 (3)	0.0329 (8)
C8	0.9520 (3)	0.5000	0.8266 (3)	0.0338 (8)
C9	1.0349 (3)	0.5000	0.7957 (4)	0.0549 (13)
H9A	1.0322	0.5000	0.7130	0.066*
C10	1.1247 (3)	0.5000	0.8898 (5)	0.080 (2)
H10A	1.1812	0.5000	0.8684	0.096*
N1	0.5005 (2)	0.5000	0.6874 (3)	0.0371 (7)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Zn1	0.0270 (3)	0.0560 (4)	0.0140 (3)	0.000	0.0046 (2)	0.000
S1	0.0278 (5)	0.0414 (5)	0.0202 (4)	0.000	−0.0030 (3)	0.000
O1W	0.0347 (10)	0.0589 (13)	0.0301 (10)	−0.0062 (9)	−0.0031 (8)	0.0086 (9)
O2	0.0468 (16)	0.0607 (18)	0.0213 (13)	0.000	0.0014 (12)	0.000
O3	0.0360 (10)	0.0440 (11)	0.0372 (10)	0.0048 (8)	−0.0033 (8)	−0.0028 (8)
C1	0.036 (2)	0.137 (4)	0.030 (2)	0.000	0.0134 (18)	0.000
C2	0.032 (2)	0.135 (4)	0.027 (2)	0.000	0.0088 (17)	0.000
C3	0.0311 (18)	0.048 (2)	0.0190 (17)	0.000	0.0089 (14)	0.000
C4	0.0294 (17)	0.058 (2)	0.0230 (17)	0.000	0.0106 (14)	0.000
C5	0.0302 (17)	0.050 (2)	0.0186 (16)	0.000	0.0044 (13)	0.000
C6	0.0194 (17)	0.120 (5)	0.029 (2)	0.000	−0.0003 (15)	0.000
C7	0.0241 (17)	0.046 (2)	0.0247 (17)	0.000	0.0027 (15)	0.000
C8	0.0244 (16)	0.049 (2)	0.0224 (16)	0.000	−0.0008 (13)	0.000
C9	0.034 (2)	0.106 (4)	0.0219 (18)	0.000	0.0048 (16)	0.000
C10	0.025 (2)	0.178 (7)	0.036 (3)	0.000	0.0093 (19)	0.000
N1	0.0307 (15)	0.065 (2)	0.0157 (13)	0.000	0.0072 (12)	0.000

Geometric parameters (Å, º) top

Zn1—O1Wⁱ	2.127 (2)	C3—C4	1.372 (5)
Zn1—O1W	2.127 (2)	C3—C3^iv	1.485 (6)
Zn1—O1Wⁱⁱ	2.127 (2)	C4—C5	1.383 (5)
Zn1—O1Wⁱⁱⁱ	2.127 (2)	C4—H4A	0.9300
Zn1—N1ⁱ	2.131 (3)	C5—N1	1.326 (5)
Zn1—N1	2.131 (3)	C5—H5A	0.9300
S1—O3ⁱⁱ	1.455 (2)	C6—C10^v	1.358 (6)
S1—O3	1.455 (2)	C6—C7	1.421 (5)
S1—O2	1.461 (3)	C6—H6A	0.9300
S1—C8	1.784 (4)	C7—C7^v	1.424 (7)
O1W—H1WA	0.846 (19)	C7—C8	1.426 (5)
O1W—H1WB	0.83 (2)	C8—C9	1.362 (6)
C1—N1	1.330 (6)	C9—C10	1.406 (6)
C1—C2	1.376 (6)	C9—H9A	0.9300
C1—H1A	0.9300	C10—C6^v	1.358 (6)
C2—C3	1.390 (6)	C10—H10A	0.9300
C2—H2A	0.9300

O1Wⁱ—Zn1—O1W	180.00 (9)	C3—C2—H2A	119.8
O1Wⁱ—Zn1—O1Wⁱⁱ	87.13 (12)	C4—C3—C2	115.3 (3)
O1W—Zn1—O1Wⁱⁱ	92.87 (12)	C4—C3—C3^iv	123.0 (4)
O1Wⁱ—Zn1—O1Wⁱⁱⁱ	92.87 (12)	C2—C3—C3^iv	121.7 (4)
O1W—Zn1—O1Wⁱⁱⁱ	87.13 (12)	C3—C4—C5	121.1 (3)
O1Wⁱⁱ—Zn1—O1Wⁱⁱⁱ	180.000 (1)	C3—C4—H4A	119.4
O1Wⁱ—Zn1—N1ⁱ	88.18 (8)	C5—C4—H4A	119.4
O1W—Zn1—N1ⁱ	91.82 (8)	N1—C5—C4	123.1 (3)
O1Wⁱⁱ—Zn1—N1ⁱ	91.82 (8)	N1—C5—H5A	118.4
O1Wⁱⁱⁱ—Zn1—N1ⁱ	88.18 (8)	C4—C5—H5A	118.4
O1Wⁱ—Zn1—N1	91.82 (8)	C10^v—C6—C7	120.7 (4)
O1W—Zn1—N1	88.18 (8)	C10^v—C6—H6A	119.7
O1Wⁱⁱ—Zn1—N1	88.18 (8)	C7—C6—H6A	119.7
O1Wⁱⁱⁱ—Zn1—N1	91.82 (8)	C6—C7—C7^v	118.6 (4)
N1ⁱ—Zn1—N1	180.0	C6—C7—C8	122.9 (3)
O3ⁱⁱ—S1—O3	111.78 (18)	C7^v—C7—C8	118.5 (4)
O3ⁱⁱ—S1—O2	112.40 (11)	C9—C8—C7	121.3 (3)
O3—S1—O2	112.40 (11)	C9—C8—S1	117.4 (3)
O3ⁱⁱ—S1—C8	107.20 (10)	C7—C8—S1	121.3 (3)
O3—S1—C8	107.20 (10)	C8—C9—C10	119.6 (4)
O2—S1—C8	105.36 (17)	C8—C9—H9A	120.2
Zn1—O1W—H1WA	126 (3)	C10—C9—H9A	120.2
Zn1—O1W—H1WB	120 (2)	C6^v—C10—C9	121.3 (4)
H1WA—O1W—H1WB	108 (3)	C6^v—C10—H10A	119.3
N1—C1—C2	123.5 (4)	C9—C10—H10A	119.3
N1—C1—H1A	118.2	C5—N1—C1	116.5 (3)
C2—C1—H1A	118.2	C5—N1—Zn1	121.4 (2)
C1—C2—C3	120.5 (4)	C1—N1—Zn1	122.1 (3)
C1—C2—H2A	119.8

N1—C1—C2—C3	0.000 (2)	C7—C8—C9—C10	0.000 (2)
C1—C2—C3—C4	0.000 (2)	S1—C8—C9—C10	180.000 (2)
C1—C2—C3—C3^iv	180.000 (2)	C8—C9—C10—C6^v	0.000 (2)
C2—C3—C4—C5	0.000 (1)	C4—C5—N1—C1	0.000 (2)
C3^iv—C3—C4—C5	180.000 (1)	C4—C5—N1—Zn1	180.000 (1)
C3—C4—C5—N1	0.000 (2)	C2—C1—N1—C5	0.000 (1)
C10^v—C6—C7—C7^v	0.000 (2)	C2—C1—N1—Zn1	180.000 (1)
C10^v—C6—C7—C8	180.000 (2)	O1Wⁱ—Zn1—N1—C5	−46.47 (6)
C6—C7—C8—C9	180.000 (2)	O1W—Zn1—N1—C5	133.53 (6)
C7^v—C7—C8—C9	0.000 (2)	O1Wⁱⁱ—Zn1—N1—C5	−133.53 (6)
C6—C7—C8—S1	0.000 (1)	O1Wⁱⁱⁱ—Zn1—N1—C5	46.47 (6)
C7^v—C7—C8—S1	180.000 (1)	N1ⁱ—Zn1—N1—C5	0 (100)
O3ⁱⁱ—S1—C8—C9	119.92 (10)	O1Wⁱ—Zn1—N1—C1	133.53 (6)
O3—S1—C8—C9	−119.92 (10)	O1W—Zn1—N1—C1	−46.47 (6)
O2—S1—C8—C9	0.0	O1Wⁱⁱ—Zn1—N1—C1	46.47 (6)
O3ⁱⁱ—S1—C8—C7	−60.08 (10)	O1Wⁱⁱⁱ—Zn1—N1—C1	−133.53 (6)
O3—S1—C8—C7	60.08 (10)	N1ⁱ—Zn1—N1—C1	180 (100)
O2—S1—C8—C7	180.000 (1)

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

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O1w—H1wa···O3	0.85 (2)	1.92 (2)	2.763 (3)	175 (3)
O1w—H1wb···O2^vi	0.83 (2)	1.95 (2)	2.768 (3)	166 (3)

Symmetry code: (vi) −x+3/2, y+1/2, −z+1.

Experimental details

Crystal data
Chemical formula	[Zn(C₁₀H₈N₂)(H₂O)₄](C₁₀H₆O₆S₂)
M_r	579.89
Crystal system, space group	Monoclinic, C2/m
Temperature (K)	293
a, b, c (Å)	14.584 (3), 7.3948 (15), 11.380 (2)
β (°)	108.38 (3)
V (Å³)	1164.7 (4)
Z	2
Radiation type	Mo Kα
µ (mm⁻¹)	1.29
Crystal size (mm)	0.38 × 0.29 × 0.19

Data collection
Diffractometer	Siemens SMART CCD area-detector diffractometer
Absorption correction	Multi-scan (SADABS; Sheldrick, 1996)
T_min, T_max	0.658, 0.794
No. of measured, independent and observed [I > 2σ(I)] reflections	5711, 1421, 1302
R_int	0.033
(sin θ/λ)_max (Å⁻¹)	0.647

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.034, 0.107, 1.03
No. of reflections	1421
No. of parameters	107
No. of restraints	15
H-atom treatment	H atoms treated by a mixture of independent and constrained refinement
Δρ_max, Δρ_min (e Å⁻³)	0.46, −0.52

Computer programs: SMART (Siemens, 1994), SAINT (Siemens, 1994), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), SHELXTL (Sheldrick, 2008).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O1w—H1wa···O3	0.85 (2)	1.92 (2)	2.763 (3)	175 (3)
O1w—H1wb···O2ⁱ	0.83 (2)	1.95 (2)	2.768 (3)	166 (3)

Symmetry code: (i) −x+3/2, y+1/2, −z+1.

Acknowledgements

This work was supported by the Natural Science Foundation of Fujian Province (No. 2008 J0172).

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