catena-Poly[[diaqua­zinc(II)]-μ-piper­azine-1,4-diacetato-κ4N1,O1:N4,O4]

Bi, J.-H.

doi:10.1107/S1600536809045462

metal-organic compounds

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ISSN: 2056-9890

Volume 65| Part 12| December 2009| Page m1561

doi:10.1107/S1600536809045462

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catena-Poly[[diaquazinc(II)]-μ-piperazine-1,4-diacetato-κ⁴N¹,O¹:N⁴,O⁴]

Jian-Hong Bi ^a ^*

^aDeparment of Chemistry and Chemical Engineering, Hefei Normal University, Hefei 230061, People's Republic of China
^*Correspondence e-mail: bi010101@126.com

(Received 24 October 2009; accepted 29 October 2009; online 11 November 2009)

The asymmetric unit of the title compound, [Zn(C₈H₁₂N₂O₄)(H₂O)₂]_n, contains a Zn^II ion residing on an inversion center, half of a centrosymmetric piperazine-1,4-diacetate ligand (L) and a water molecule. The Zn^II ion is trans-coordinated by two N,O-bidentate L ligands and by two water molecules in a distorted octahedral geometry. In the crystal structure, intermolecular O—H⋯O hydrogen bonds link polymeric chains into a three-dimensional supramolecular structure.

Related literature

For related structures, see: Wu & Mak (1996 ); Zhang & Chen (2003 ); Shen et al. (2006 ); Yang et al. (2008 ); Zhang et al. (2008 ).

Experimental

Crystal data

[Zn(C₈H₁₂N₂O₄)(H₂O)₂]
M_r = 301.62
Monoclinic, P 2₁ /c
a = 6.3670 (1) Å
b = 7.3116 (10) Å
c = 11.9910 (1) Å
β = 101.438 (10)°
V = 547.13 (1) Å³
Z = 2
Mo Kα radiation
μ = 2.27 mm⁻¹
T = 291 K
0.30 × 0.15 × 0.12 mm

Data collection

Bruker SMART CCD area-detector diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2000 ) T_min = 0.517, T_max = 0.766
5254 measured reflections
1255 independent reflections
1173 reflections with I > 2σ(I)
R_int = 0.014

Refinement

R[F² > 2σ(F²)] = 0.018
wR(F²) = 0.050
S = 1.07
1255 reflections
87 parameters
2 restraints
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.35 e Å⁻³
Δρ_min = −0.17 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O3—H3A⋯O1ⁱ	0.813 (19)	2.000 (19)	2.8060 (16)	172.9 (19)
O3—H3B⋯O1ⁱⁱ	0.826 (15)	1.927 (15)	2.7497 (15)	175 (2)
Symmetry codes: (i) $[x, -y+{\script{1\over 2}}, z+{\script{1\over 2}}]$ ; (ii) -x+1, -y+1, -z+1.

Data collection: SMART (Bruker, 2000); cell refinement: SAINT (Bruker, 2000); data reduction: SAINT; program(s) used to solve structure: SHELXTL (Sheldrick, 2008 ); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL.

Supporting information

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536809045462/cv2645sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536809045462/cv2645Isup2.hkl

checkCIF report

Comment top

Researchers have shown their interest in design and synthesis of polydentate flexible ligands, which propagated a family of piperazine-based ligands, because the chair configuration of piperazine can reduce their coordination modes, which makes piperazine or its related species structurally or functionally directing polymeric constructions (Shen et al., 2006; Wu et al., 1996; Yang et al., 2008; Zhang et al., 2008; Zhang et al., 2003). Herein, based on bridging 1,4-piperazinediacetic acid, we report the title compound and present its crystal structure.

The coordination geometry about Zn(II) center is shown in Fig.1. The Zn(II) center adopts an octahedral coordination geometry, in which two N atoms and two O atoms from two ligands are in the equatorial plane while the apical positions are occupied by two O atoms from water molecules. Intermolecular O—H···O hydrogen bonds (Table 1) link polymeric chains into three-dimensional supramolecular structure.

Related literature top

For related structures, see: Wu & Mak (1996); Zhang & Chen (2003); Shen et al. (2006); Yang et al. (2008); Zhang et al. (2008).

Experimental top

All solvents and chemicals were of analytical grade and were used without further purification. A mixture of H₂L.2HCl (0.1 mmol), ZnCl₂ (0.1 mmol), and water (10 ml) were heated in a 15-ml Teflon-lined vessel at 120 oC for 3 days, followed by slow cooling (5 oC h-1) to room temperature. After filtration and washing with H₂O, colorless block crystals were collected and dried in air. Anal. Calcd.for C₈H₁₆N₂O₆Zn: C, 31.86; H, 5.35; N, 9.29. Found: C, 31.88; H,5.39; N, 9.22.

Computing details top

Data collection: SMART (Bruker, 2000); cell refinement: SAINT (Bruker, 2000); data reduction: SAINT (Bruker, 2000); program(s) used to solve structure: SHELXTL (Sheldrick, 2008); program(s) used to refine structure: SHELXTL (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXTL (Sheldrick, 2008).

Figures top

Fig. 1. A portion of the polymeric chain in (I) showing 30% probability displacement ellipsoids and the atomic numbering [symmetry codes: (A) 1 - x, -y, 1 - z; (B) -x, -y, 1 - z].

catena-Poly[[diaquazinc(II)]-µ-piperazine-1,4-diacetato- κ⁴N¹,O¹:N⁴,O⁴] top

Crystal data top

[Zn(C₈H₁₂N₂O₄)(H₂O)₂]	F(000) = 312.0
M_r = 301.62	D_x = 1.831 Mg m⁻³
Monoclinic, P2₁/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 1255 reflections
a = 6.3670 (1) Å	θ = 3.3–27.5°
b = 7.3116 (1) Å	µ = 2.27 mm⁻¹
c = 11.9910 (1) Å	T = 291 K
β = 101.438 (1)°	Block, colourless
V = 547.13 (1) Å³	0.30 × 0.15 × 0.12 mm
Z = 2

Data collection top

Bruker SMART CCD area-detector diffractometer	1255 independent reflections
Radiation source: fine-focus sealed tube	1173 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.014
ϕ and ω scans	θ_max = 27.5°, θ_min = 3.3°
Absorption correction: multi-scan (SADABS; Bruker, 2000)	h = −8→8
T_min = 0.517, T_max = 0.766	k = −7→9
5254 measured reflections	l = −15→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)] = 0.018	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.050	H atoms treated by a mixture of independent and constrained refinement
S = 1.07	w = 1/[σ²(F_o²) + (0.0264P)² + 0.2196P] where P = (F_o² + 2F_c²)/3
1255 reflections	(Δ/σ)_max < 0.001
87 parameters	Δρ_max = 0.35 e Å⁻³
2 restraints	Δρ_min = −0.17 e Å⁻³

Crystal data top

[Zn(C₈H₁₂N₂O₄)(H₂O)₂]	V = 547.13 (1) Å³
M_r = 301.62	Z = 2
Monoclinic, P2₁/c	Mo Kα radiation
a = 6.3670 (1) Å	µ = 2.27 mm⁻¹
b = 7.3116 (1) Å	T = 291 K
c = 11.9910 (1) Å	0.30 × 0.15 × 0.12 mm
β = 101.438 (1)°

Data collection top

Bruker SMART CCD area-detector diffractometer	1255 independent reflections
Absorption correction: multi-scan (SADABS; Bruker, 2000)	1173 reflections with I > 2σ(I)
T_min = 0.517, T_max = 0.766	R_int = 0.014
5254 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.018	2 restraints
wR(F²) = 0.050	H atoms treated by a mixture of independent and constrained refinement
S = 1.07	Δρ_max = 0.35 e Å⁻³
1255 reflections	Δρ_min = −0.17 e Å⁻³
87 parameters

Special details top

Experimental. The structure was solved by direct methods (Bruker, 2000) and successive difference Fourier syntheses.

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	0.3930 (2)	0.34321 (18)	0.39316 (11)	0.0202 (3)
C2	0.2110 (2)	0.32565 (19)	0.45839 (13)	0.0246 (3)
H2A	0.2484	0.3936	0.5290	0.029*
H2B	0.0826	0.3804	0.4137	0.029*
C3	0.0594 (2)	0.1341 (2)	0.58516 (12)	0.0223 (3)
H3C	−0.0658	0.2127	0.5701	0.027*
H3D	0.1581	0.1831	0.6505	0.027*
C4	0.0075 (2)	0.0568 (2)	0.38757 (12)	0.0221 (3)
H4A	0.0714	0.0528	0.3206	0.026*
H4B	−0.1179	0.1350	0.3709	0.026*
H3A	0.547 (3)	0.101 (3)	0.7111 (15)	0.043 (6)*
H3B	0.607 (3)	0.255 (2)	0.6608 (17)	0.042 (6)*
N1	0.16401 (17)	0.13433 (15)	0.48462 (10)	0.0198 (2)
O1	0.3977 (2)	0.48174 (13)	0.33348 (10)	0.0299 (2)
O2	0.53370 (15)	0.22018 (14)	0.40554 (9)	0.0263 (2)
O3	0.59517 (17)	0.14245 (15)	0.65815 (9)	0.0265 (2)
Zn1	0.5000	0.0000	0.5000	0.02027 (9)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
C1	0.0241 (6)	0.0172 (6)	0.0196 (6)	−0.0029 (5)	0.0052 (5)	−0.0009 (5)
C2	0.0228 (6)	0.0188 (7)	0.0346 (8)	0.0020 (5)	0.0116 (6)	0.0021 (6)
C3	0.0198 (6)	0.0264 (7)	0.0224 (7)	−0.0021 (5)	0.0080 (5)	−0.0027 (5)
C4	0.0188 (6)	0.0276 (7)	0.0205 (6)	−0.0001 (5)	0.0054 (5)	0.0020 (6)
N1	0.0185 (5)	0.0198 (5)	0.0228 (6)	−0.0020 (4)	0.0081 (4)	0.0006 (4)
O1	0.0418 (6)	0.0197 (5)	0.0307 (6)	0.0016 (4)	0.0131 (5)	0.0068 (4)
O2	0.0255 (5)	0.0224 (5)	0.0351 (6)	0.0040 (4)	0.0162 (4)	0.0083 (4)
O3	0.0328 (5)	0.0225 (5)	0.0270 (5)	−0.0011 (4)	0.0125 (4)	−0.0019 (4)
Zn1	0.02321 (13)	0.01652 (13)	0.02233 (13)	0.00056 (7)	0.00751 (9)	0.00295 (8)

Geometric parameters (Å, º) top

C1—O1	1.2439 (17)	C4—C3ⁱ	1.514 (2)
C1—O2	1.2575 (16)	C4—H4A	0.9700
C1—C2	1.5269 (18)	C4—H4B	0.9700
C2—N1	1.4773 (17)	N1—Zn1	2.3278 (11)
C2—H2A	0.9700	O2—Zn1	2.0042 (10)
C2—H2B	0.9700	O3—Zn1	2.1430 (11)
C3—N1	1.4884 (16)	O3—H3A	0.814 (15)
C3—C4ⁱ	1.514 (2)	O3—H3B	0.825 (16)
C3—H3C	0.9700	Zn1—O2ⁱⁱ	2.0042 (10)
C3—H3D	0.9700	Zn1—O3ⁱⁱ	2.1430 (11)
C4—N1	1.4864 (18)	Zn1—N1ⁱⁱ	2.3278 (11)

O1—C1—O2	123.53 (12)	C4—N1—C3	107.18 (10)
O1—C1—C2	118.08 (12)	C2—N1—Zn1	101.23 (7)
O2—C1—C2	118.34 (12)	C4—N1—Zn1	111.36 (8)
N1—C2—C1	113.26 (11)	C3—N1—Zn1	119.15 (8)
N1—C2—H2A	108.9	C1—O2—Zn1	119.19 (8)
C1—C2—H2A	108.9	Zn1—O3—H3A	115.2 (15)
N1—C2—H2B	108.9	Zn1—O3—H3B	121.7 (14)
C1—C2—H2B	108.9	H3A—O3—H3B	112 (2)
H2A—C2—H2B	107.7	O2ⁱⁱ—Zn1—O2	180.0
N1—C3—C4ⁱ	111.49 (11)	O2ⁱⁱ—Zn1—O3	86.18 (4)
N1—C3—H3C	109.3	O2—Zn1—O3	93.82 (4)
C4ⁱ—C3—H3C	109.3	O2ⁱⁱ—Zn1—O3ⁱⁱ	93.82 (4)
N1—C3—H3D	109.3	O2—Zn1—O3ⁱⁱ	86.18 (4)
C4ⁱ—C3—H3D	109.3	O3—Zn1—O3ⁱⁱ	180.0
H3C—C3—H3D	108.0	O2ⁱⁱ—Zn1—N1	100.60 (4)
N1—C4—C3ⁱ	110.87 (11)	O2—Zn1—N1	79.40 (4)
N1—C4—H4A	109.5	O3—Zn1—N1	87.66 (4)
C3ⁱ—C4—H4A	109.5	O3ⁱⁱ—Zn1—N1	92.34 (4)
N1—C4—H4B	109.5	O2ⁱⁱ—Zn1—N1ⁱⁱ	79.40 (4)
C3ⁱ—C4—H4B	109.5	O2—Zn1—N1ⁱⁱ	100.60 (4)
H4A—C4—H4B	108.1	O3—Zn1—N1ⁱⁱ	92.34 (4)
C2—N1—C4	109.09 (11)	O3ⁱⁱ—Zn1—N1ⁱⁱ	87.66 (4)
C2—N1—C3	108.39 (10)	N1—Zn1—N1ⁱⁱ	180.00 (6)

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

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O3—H3A···O1ⁱⁱⁱ	0.81 (2)	2.00 (2)	2.8060 (16)	173 (2)
O3—H3B···O1^iv	0.83 (2)	1.93 (2)	2.7497 (15)	175 (2)

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

Experimental details

Crystal data
Chemical formula	[Zn(C₈H₁₂N₂O₄)(H₂O)₂]
M_r	301.62
Crystal system, space group	Monoclinic, P2₁/c
Temperature (K)	291
a, b, c (Å)	6.3670 (1), 7.3116 (1), 11.9910 (1)
β (°)	101.438 (1)
V (Å³)	547.13 (1)
Z	2
Radiation type	Mo Kα
µ (mm⁻¹)	2.27
Crystal size (mm)	0.30 × 0.15 × 0.12

Data collection
Diffractometer	Bruker SMART CCD area-detector diffractometer
Absorption correction	Multi-scan (SADABS; Bruker, 2000)
T_min, T_max	0.517, 0.766
No. of measured, independent and observed [I > 2σ(I)] reflections	5254, 1255, 1173
R_int	0.014
(sin θ/λ)_max (Å⁻¹)	0.649

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.018, 0.050, 1.07
No. of reflections	1255
No. of parameters	87
No. of restraints	2
H-atom treatment	H atoms treated by a mixture of independent and constrained refinement
Δρ_max, Δρ_min (e Å⁻³)	0.35, −0.17

Computer programs: SMART (Bruker, 2000), SAINT (Bruker, 2000), SHELXTL (Sheldrick, 2008).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O3—H3A···O1ⁱ	0.813 (19)	2.000 (19)	2.8060 (16)	172.9 (19)
O3—H3B···O1ⁱⁱ	0.826 (15)	1.927 (15)	2.7497 (15)	175 (2)

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

Acknowledgements

The author is indebted to the National Natural Science Foundation of China (grant No. 20871039) for financial support.

References

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