catena-Poly[zinc(II)-μ-aqua-κ2O:O-bis­(μ-quinoline-4-carboxyl­ato-κ2O:O′)]

Chen, J.-X.; Meng, W.-W.

doi:10.1107/S1600536809025392

metal-organic compounds

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ISSN: 2056-9890

Volume 65| Part 8| August 2009| Page m873

doi:10.1107/S1600536809025392

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catena-Poly[zinc(II)-μ-aqua-κ²O:O-bis(μ-quinoline-4-carboxylato-κ²O:O′)]

Jin-Xi Chen ^a ^* and Wei-Wei Meng ^a

^aSchool of Chemistry and Chemical Engineering, Southeast University, Nanjing 211189, People's Republic of China
^*Correspondence e-mail: mww_514730@163.com

(Received 26 June 2009; accepted 1 July 2009; online 4 July 2009)

The asymmetric unit of the title complex, [Zn(C₁₀H₆NO₂)₂(H₂O)]_n, consists of one quinoline-4-carboxylate anion, half of a Zn²⁺ cation and half of a coordinated water molecule. The cation and the water O atom have crystallographically imposed inversion and twofold rotation symmetry, respectively. The metal centre displays an elongated ZnO₆ octahedral coordination geometry provided by the O atoms of four anions at the equatorial plane and two axial water molecules. Each anion and water molecule act as bridges between Zn^II cations, forming a polymeric chain parallel to [001]. The chains are further linked into a three-dimensional framework through O—H⋯N hydrogen bonds.

Related literature

For the coordination chemistry of transition metal complexes with quinoline-4-carboxylate, see: Bu et al. (2004 , 2005 ); Xiong et al. (2000 ); Chen et al. (2002 ).

Experimental

Crystal data

[Zn(C₁₀H₆NO₂)₂(H₂O)]
M_r = 427.72
Monoclinic, C 2/c
a = 14.929 (2) Å
b = 14.4025 (13) Å
c = 7.5428 (11) Å
β = 91.961 (6)°
V = 1620.8 (4) Å³
Z = 4
Mo Kα radiation
μ = 1.56 mm⁻¹
T = 293 K
0.30 × 0.30 × 0.20 mm

Data collection

Rigaku SCXmini diffractometer
Absorption correction: multi-scan (CrystalClear; Rigaku/MSC, 2005 ) T_min = 0.635, T_max = 0.732
5552 measured reflections
1831 independent reflections
1741 reflections with I > 2σ(I)
R_int = 0.030

Refinement

R[F² > 2σ(F²)] = 0.026
wR(F²) = 0.069
S = 1.09
1831 reflections
129 parameters
H-atom parameters constrained
Δρ_max = 0.38 e Å⁻³
Δρ_min = −0.82 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O3—H7⋯N1ⁱ	0.90	1.89	2.7920 (15)	174
Symmetry code: (i) $[x+{\script{1\over 2}}, y+{\script{1\over 2}}, z]$ .

Data collection: CrystalClear (Rigaku/MSC, 2005); cell refinement: CrystalClear; data reduction: CrystalClear; 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.

Supporting information

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536809025392/rz2342sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536809025392/rz2342Isup2.hkl

checkCIF report

Comment top

In recent years, new coordination compounds based on transition metals and quinoline-4-carboxylic acid have attracted much attention because of the role of non-covalent supramolecular interactions such as hydrogen bonding or π-π conjugate effect (Bu et al. 2005). However, the use of quinoline-4-carboxylic acid for the construction of metal-organic frameworks has not been well documented yet (Bu et al., 2004; Xiong et al., 2000; Chen et al., 2002).

The asymmetric unit of the title complex polymer (Fig. 1) consists of one quinoline-4-carboxylate anion, half of a zinc(II) cation and half of a coordinated water molecule. The cation and the water oxygen atom have crystallographically imposed inversion and twofold rotation symmetry, respectively. The geometry around the zinc(II) metal centre can be best described as elongated octahedral, with four oxygen atoms from four independent quinoline-4-carboxylate anions at the equatorial plane and two oxygen atoms from two H₂O molecules at the axial position. Each quinoline-4-carboxylate anion adopts an O,O'-bidentate bridging mode. Adjacent zinc(II) cations are bridged by the quinoline-4-carboxylate ligands and water molecules, forming a chain parallel to [001] (Fig. 2). The chains are further linked into a three-dimensional network (Fig. 3) by O—H···N hydrogen bonds (Table 1).

Related literature top

For the coordination chemistry of transition metal complexes with quinoline-4-carboxylate, see: Bu et al. (2004, 2005); Xiong et al. (2000); Chen et al. (2002).

Experimental top

The title compound was synthesized by the solvothermal reaction of Zn(NO₃)₂.6H₂O (0.2 mmol, 0.0595 g), 4-quinolinecarboxylic acid (0.6 mmol, 0.1039 g) and C₂H₅OH/H₂O (4:1 v/v; 5 ml) in a Teflon-lined autoclave at 180°C for 3 days. After the reaction autoclave was slowly cooled to room temperature for 24 h, light yellow block single crystals suitable for X-ray diffraction analysis were obtained, isolated by filtration and washed with water.

Computing details top

Data collection: CrystalClear (Rigaku/MSC, 2005); cell refinement: CrystalClear (Rigaku/MSC, 2005); data reduction: CrystalClear (Rigaku/MSC, 2005); 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. The asymmetric unit of the title compound, with displacement ellipsoids drawn at the 30% probability level.
	Fig. 2. Partial crystal packing of the title compound, showing the polymeric chain parallel to [001]. Hydrogen atoms are omitted for clarity.
	Fig. 3. Crystal packing of the title compound viewed along the c axis. N—H···O hydrogen bonds are shown as dashed lines. Hydrogen atoms not involved in hydrogen bonding are omitted for clarity.

catena-Poly[zinc(II)-µ-aqua-κ²O:O-bis(µ-quinoline- 4-carboxylato-κ²O:O')] top

Crystal data top

[Zn(C₁₀H₆NO₂)₂(H₂O)]	F(000) = 872
M_r = 427.72	D_x = 1.753 Mg m⁻³
Monoclinic, C2/c	Mo Kα radiation, λ = 0.71070 Å
Hall symbol: -C 2yc	Cell parameters from 30 reflections
a = 14.929 (2) Å	θ = 3.3–27.5°
b = 14.4025 (13) Å	µ = 1.56 mm⁻¹
c = 7.5428 (11) Å	T = 293 K
β = 91.961 (6)°	Block, light yellow
V = 1620.8 (4) Å³	0.30 × 0.30 × 0.20 mm
Z = 4

Data collection top

Rigaku SCXmini diffractometer	1831 independent reflections
Radiation source: fine-focus sealed tube	1741 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.030
ω scans	θ_max = 27.5°, θ_min = 3.3°
Absorption correction: multi-scan (CrystalClear; Rigaku/MSC, 2005)	h = −18→19
T_min = 0.635, T_max = 0.732	k = −15→18
5552 measured reflections	l = −7→9

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)] = 0.026	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.069	H-atom parameters constrained
S = 1.09	w = 1/[σ²(F_o²) + (0.0375P)² + 1.5104P] where P = (F_o² + 2F_c²)/3
1831 reflections	(Δ/σ)_max < 0.001
129 parameters	Δρ_max = 0.38 e Å⁻³
0 restraints	Δρ_min = −0.82 e Å⁻³

Crystal data top

[Zn(C₁₀H₆NO₂)₂(H₂O)]	V = 1620.8 (4) Å³
M_r = 427.72	Z = 4
Monoclinic, C2/c	Mo Kα radiation
a = 14.929 (2) Å	µ = 1.56 mm⁻¹
b = 14.4025 (13) Å	T = 293 K
c = 7.5428 (11) Å	0.30 × 0.30 × 0.20 mm
β = 91.961 (6)°

Data collection top

Rigaku SCXmini diffractometer	1831 independent reflections
Absorption correction: multi-scan (CrystalClear; Rigaku/MSC, 2005)	1741 reflections with I > 2σ(I)
T_min = 0.635, T_max = 0.732	R_int = 0.030
5552 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.026	0 restraints
wR(F²) = 0.069	H-atom parameters constrained
S = 1.09	Δρ_max = 0.38 e Å⁻³
1831 reflections	Δρ_min = −0.82 e Å⁻³
129 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	0.01513 (10)
O1	0.40680 (9)	0.40753 (9)	0.38283 (15)	0.0330 (3)
O2	0.39589 (8)	0.42662 (9)	0.08731 (15)	0.0325 (3)
O3	0.5000	0.58494 (9)	0.2500	0.0162 (3)
N1	0.14620 (8)	0.20508 (9)	0.23221 (16)	0.0219 (3)
C1	0.22399 (11)	0.18428 (10)	0.3075 (2)	0.0224 (3)
C2	0.29962 (10)	0.24374 (10)	0.3085 (2)	0.0214 (3)
C3	0.29358 (10)	0.32726 (10)	0.22272 (18)	0.0179 (3)
C4	0.19859 (11)	0.43283 (11)	0.0286 (2)	0.0266 (3)
C5	0.11735 (13)	0.45081 (12)	−0.0528 (2)	0.0342 (4)
C6	0.04541 (12)	0.38852 (14)	−0.0379 (2)	0.0353 (4)
C7	0.05608 (11)	0.30808 (13)	0.0555 (2)	0.0293 (3)
C8	0.13929 (10)	0.28722 (10)	0.14128 (19)	0.0200 (3)
C9	0.21217 (9)	0.35055 (10)	0.13033 (18)	0.0185 (3)
C10	0.37322 (9)	0.39320 (10)	0.23183 (19)	0.0193 (3)
H1	0.2299	0.1255	0.3648	0.027*
H2	0.3543	0.2252	0.3697	0.026*
H3	0.2469	0.4754	0.0182	0.032*
H4	0.1092	0.5063	−0.1217	0.041*
H5	−0.0115	0.4034	−0.0929	0.043*
H6	0.0073	0.2655	0.0619	0.035*
H7	0.5454	0.6264	0.2501	0.021*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Zn1	0.01229 (15)	0.01835 (14)	0.01481 (15)	0.00068 (7)	0.00133 (9)	−0.00354 (7)
O1	0.0360 (7)	0.0416 (7)	0.0210 (6)	−0.0229 (5)	−0.0037 (5)	−0.0001 (5)
O2	0.0303 (6)	0.0465 (7)	0.0211 (5)	−0.0222 (5)	0.0049 (5)	−0.0001 (5)
O3	0.0148 (6)	0.0152 (6)	0.0186 (7)	0.000	0.0000 (5)	0.000
N1	0.0216 (6)	0.0240 (6)	0.0203 (6)	−0.0082 (5)	0.0032 (5)	−0.0022 (5)
C1	0.0273 (8)	0.0196 (6)	0.0205 (7)	−0.0041 (6)	0.0028 (6)	0.0014 (5)
C2	0.0194 (7)	0.0261 (7)	0.0186 (6)	−0.0026 (5)	0.0004 (5)	−0.0005 (5)
C3	0.0182 (7)	0.0212 (6)	0.0144 (6)	−0.0058 (5)	0.0043 (5)	−0.0042 (5)
C4	0.0309 (8)	0.0220 (7)	0.0273 (7)	−0.0018 (6)	0.0061 (6)	0.0004 (6)
C5	0.0382 (10)	0.0338 (8)	0.0309 (9)	0.0100 (7)	0.0044 (7)	0.0077 (7)
C6	0.0255 (8)	0.0503 (10)	0.0299 (9)	0.0083 (7)	−0.0008 (7)	0.0037 (8)
C7	0.0192 (7)	0.0421 (9)	0.0268 (8)	−0.0034 (6)	0.0018 (6)	−0.0010 (7)
C8	0.0185 (7)	0.0250 (7)	0.0167 (6)	−0.0040 (5)	0.0030 (5)	−0.0026 (5)
C9	0.0196 (7)	0.0199 (6)	0.0162 (6)	−0.0029 (5)	0.0039 (5)	−0.0037 (5)
C10	0.0171 (7)	0.0217 (6)	0.0193 (7)	−0.0065 (5)	0.0023 (5)	−0.0032 (5)

Geometric parameters (Å, º) top

Zn1—O2ⁱ	2.0090 (11)	C2—C3	1.367 (2)
Zn1—O2ⁱⁱ	2.0090 (11)	C2—H2	0.96
Zn1—O1ⁱⁱⁱ	2.0991 (11)	C3—C9	1.420 (2)
Zn1—O1	2.0991 (11)	C3—C10	1.5213 (19)
Zn1—O3	2.2478 (7)	C4—C5	1.365 (3)
Zn1—O3ⁱⁱⁱ	2.2478 (7)	C4—C9	1.422 (2)
O1—C10	1.2459 (18)	C4—H3	0.95
O2—C10	1.2489 (18)	C5—C6	1.407 (3)
O2—Zn1ⁱⁱ	2.0090 (11)	C5—H4	0.96
O3—Zn1ⁱⁱ	2.2478 (7)	C6—C7	1.362 (3)
O3—H7	0.90	C6—H5	0.96
N1—C1	1.310 (2)	C7—C8	1.413 (2)
N1—C8	1.3695 (19)	C7—H6	0.95
C1—C2	1.417 (2)	C8—C9	1.4244 (19)
C1—H1	0.95

O2ⁱ—Zn1—O2ⁱⁱ	180.0	C1—C2—H2	119.9
O2ⁱ—Zn1—O1ⁱⁱⁱ	92.14 (6)	C2—C3—C9	118.77 (13)
O2ⁱⁱ—Zn1—O1ⁱⁱⁱ	87.86 (6)	C2—C3—C10	119.28 (13)
O2ⁱ—Zn1—O1	87.86 (6)	C9—C3—C10	121.94 (13)
O2ⁱⁱ—Zn1—O1	92.14 (6)	C5—C4—C9	120.58 (15)
O1ⁱⁱⁱ—Zn1—O1	180.0	C5—C4—H3	120.3
O2ⁱ—Zn1—O3	90.62 (4)	C9—C4—H3	119.1
O2ⁱⁱ—Zn1—O3	89.38 (4)	C4—C5—C6	120.78 (16)
O1ⁱⁱⁱ—Zn1—O3	89.36 (4)	C4—C5—H4	119.8
O1—Zn1—O3	90.64 (4)	C6—C5—H4	119.4
O2ⁱ—Zn1—O3ⁱⁱⁱ	89.38 (4)	C7—C6—C5	120.50 (16)
O2ⁱⁱ—Zn1—O3ⁱⁱⁱ	90.62 (4)	C7—C6—H5	120.1
O1ⁱⁱⁱ—Zn1—O3ⁱⁱⁱ	90.64 (4)	C5—C6—H5	119.4
O1—Zn1—O3ⁱⁱⁱ	89.36 (4)	C6—C7—C8	120.20 (15)
O3—Zn1—O3ⁱⁱⁱ	180.00 (6)	C6—C7—H6	119.8
C10—O1—Zn1	136.90 (10)	C8—C7—H6	120.0
C10—O2—Zn1ⁱⁱ	136.44 (10)	N1—C8—C7	117.58 (13)
Zn1ⁱⁱ—O3—Zn1	114.05 (6)	N1—C8—C9	122.53 (13)
Zn1ⁱⁱ—O3—H7	109.9	C7—C8—C9	119.90 (14)
Zn1—O3—H7	112.4	C3—C9—C4	124.42 (13)
C1—N1—C8	117.71 (12)	C3—C9—C8	117.57 (13)
N1—C1—C2	123.96 (14)	C4—C9—C8	118.01 (14)
N1—C1—H1	117.8	O1—C10—O2	128.43 (13)
C2—C1—H1	118.2	O1—C10—C3	115.72 (13)
C3—C2—C1	119.31 (14)	O2—C10—C3	115.84 (13)
C3—C2—H2	120.8

Symmetry codes: (i) x, −y+1, z+1/2; (ii) −x+1, y, −z+1/2; (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
O3—H7···N1^iv	0.90	1.89	2.7920 (15)	174

Symmetry code: (iv) x+1/2, y+1/2, z.

Experimental details

Crystal data
Chemical formula	[Zn(C₁₀H₆NO₂)₂(H₂O)]
M_r	427.72
Crystal system, space group	Monoclinic, C2/c
Temperature (K)	293
a, b, c (Å)	14.929 (2), 14.4025 (13), 7.5428 (11)
β (°)	91.961 (6)
V (Å³)	1620.8 (4)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	1.56
Crystal size (mm)	0.30 × 0.30 × 0.20

Data collection
Diffractometer	Rigaku SCXmini diffractometer
Absorption correction	Multi-scan (CrystalClear; Rigaku/MSC, 2005)
T_min, T_max	0.635, 0.732
No. of measured, independent and observed [I > 2σ(I)] reflections	5552, 1831, 1741
R_int	0.030
(sin θ/λ)_max (Å⁻¹)	0.649

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.026, 0.069, 1.09
No. of reflections	1831
No. of parameters	129
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.38, −0.82

Computer programs: CrystalClear (Rigaku/MSC, 2005), 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
O3—H7···N1ⁱ	0.90	1.89	2.7920 (15)	174

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

Acknowledgements

We gratefully acknowledge financial support by the start-up fund of Southeast University.

References

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