catena-Poly[[diaqua­zinc(II)]-μ-4,4′-(methyl­enedioxy)­dibenzoato]

Xu, L.; Guo, Y.; Yuan, X.

doi:10.1107/S1600536809006965

metal-organic compounds

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ISSN: 2056-9890

Volume 65| Part 4| April 2009| Page m360

doi:10.1107/S1600536809006965

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catena-Poly[[diaquazinc(II)]-μ-4,4′-(methylenedioxy)dibenzoato]

Lei Xu,^a,^b Yingna Guo ^a and Xing Yuan ^a ^*

^aCollege of Urban and Environmental Sciences, Northeast Normal University, Changchun 130024, People's Republic of China, and ^bSchool of Chemistry and Environmental Engineering, Changchun University of Science and Technology, Changchun 130022, People's Republic of China
^*Correspondence e-mail: yuanx@nenu.edu.cn

(Received 23 February 2009; accepted 25 February 2009; online 6 March 2009)

In the title complex, [Zn(C₁₅H₁₀O₆)(H₂O)₂]_n, the Zn^II atom is located on a twofold rotation axis and exhibits a distorted tetrahedral coordination environment defined by two O atoms from two 4,4′-(methylenedioxy)dibenzoate ligands and two O atoms from two coordinated water molecules. In the crystal structure, molecules are linked into a three-dimensional framework by O—H⋯O hydrogen bonds and C—H⋯π interactions.

Related literature

For the potential properties and structural topologies of metal-organic complexes involving polycarboxylate ligands, see: Chen & Liu (2002 ); Han et al. (2009 ); Li et al. (2007 ).

Experimental

Crystal data

[Zn(C₁₅H₁₀O₆)(H₂O)₂]
M_r = 387.63
Monoclinic, P 2/c
a = 13.496 (1) Å
b = 4.931 (1) Å
c = 12.357 (1) Å
β = 113.352 (1)°
V = 755.0 (2) Å³
Z = 2
Mo Kα radiation
μ = 1.67 mm⁻¹
T = 293 K
0.21 × 0.19 × 0.15 mm

Data collection

Rigaku R-AXIS RAPID diffractometer
Absorption correction: multi-scan (ABSCOR; Higashi, 1995 ) T_min = 0.707, T_max = 0.780
4318 measured reflections
1696 independent reflections
1461 reflections with I > 2σ(I)
R_int = 0.027

Refinement

R[F² > 2σ(F²)] = 0.032
wR(F²) = 0.075
S = 1.06
1696 reflections
118 parameters
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.25 e Å⁻³
Δρ_min = −0.30 e Å⁻³

Table 1
Selected geometric parameters (Å, °)

Zn1—O1	1.9582 (18)
Zn1—O4	1.975 (2)

O1—Zn1—O1ⁱ	102.26 (11)
O1—Zn1—O4	99.87 (9)
O1ⁱ—Zn1—O4	132.40 (8)
O4—Zn1—O4ⁱ	95.27 (13)
Symmetry code: (i) $[-x, y, -z+{\script{1\over 2}}]$ .

Table 2
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O4—H1⋯O1ⁱⁱ	0.74 (3)	2.13 (3)	2.851 (3)	167 (3)
O4—H2⋯O2ⁱⁱⁱ	0.88 (4)	1.78 (4)	2.657 (3)	177 (4)
C8—H8A⋯Cg3^iv	0.97	2.97	3.741 (3)	137
C8—H8B⋯Cg3^v	0.97	2.97	3.741 (3)	137
Symmetry codes: (ii) x, y-1, z; (iii) $[x, -y, z-{\script{1\over 2}}]$ ; (iv) x, y+1, z; (v) $[-x+1, y+1, -z+{\script{3\over 2}}]$ . Cg3 is the centroid of the C2–C7 benzene ring.

Data collection: PROCESS-AUTO (Rigaku, 1998 ); cell refinement: PROCESS-AUTO; data reduction: PROCESS-AUTO; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: SHELXTL-Plus (Sheldrick, 2008); software used to prepare material for publication: SHELXL97.

Supporting information

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536809006965/at2728sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536809006965/at2728Isup2.hkl

checkCIF report

Comment top

Recently, the area of metal-organic framework materials has become one of the intense research activity for their fascinating structural diversities and potential applications in catalysis, nonlinear optics and molecular sensing. As an important family of multidentate O-donor ligands, organic aromatic polycarboxylate ligands have been extensively employed in the preparation of metal-organic complexes because of their potential properties and intriguing structural topologies (Han et al., 2009; Li et al., 2007; Chen et al., 2002). Herein, we report the structure of the title complex with bis(4-benzoateoxyl)methane and zinc, [Zn(C₁₅H₁₀O₆)(H₂O)₂] (I).

Single-crystal X-ray diffraction analyses revealed Zn(II) is tetra-coordinated and exhibits tetrahedral coordination environment supplied by two bis(4-benzoateoxyl)methane O atoms and two water molecules (Fig. 1). The Zn—O bond lengthes are in the normal range (Table 1). The bis(4-benzoateoxyl)methane ligand adopts bidentate coordinated modes and bond with two zinc ions to form a chain. Adjacent chains are linked by O—H···O hydrogen bonds and C—H···π interactions into a three-dimensional supramolecular network structure (Fig. 2, Table 2).

Related literature top

For the potential properties and structural topologies of metal-organic complexes involving polycarboxylate ligands, see: Chen & Liu (2002); Han et al. (2009); Li et al. (2007). Cg3 is the centroid of the C2–C7 benzene ring.

Experimental top

Zinc(II) acetate dihydrate (0.066 g, 0.3 mol), bis(4-benzoateoxyl)methane (0.058 g, 0.2 mmol), sodium hydroxide (0.016 g, 0.4 mmol) and water (14 ml) were placed in a 23 ml Teflon-lined autoclave, and the autoclave was heated at 423 K for 3 d. After cooling slowly to room temperature at a rate of 10 K h^-1, colourless crystals of (I) were obtained.

Computing details top

Data collection: PROCESS-AUTO (Rigaku, 1998); cell refinement: PROCESS-AUTO (Rigaku, 1998); data reduction: PROCESS-AUTO (Rigaku, 1998); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: SHELXTL-Plus (Sheldrick, 2008); software used to prepare material for publication: SHELXL97 (Sheldrick, 2008).

Figures top

	Fig. 1. View of the local coordination of Zn(II) with the atomic numbering scheme. Displacement ellipsoids are drawn at the 30% probability level.
	Fig. 2. A packing diagram for the three-dimensional supramolecular framework via O—H···O interactions. The view direction is parallel to the a axis. Hydrogen bonds are indicated by dashed lines.

catena-Poly[[diaquazinc(II)]-µ-4,4'-(methylenedioxy)dibenzoato] top

Crystal data top

[Zn(C₁₅H₁₀O₆)(H₂O)₂]	F(000) = 396
M_r = 387.63	D_x = 1.705 Mg m⁻³
Monoclinic, P2/c	Mo Kα radiation, λ = 0.71069 Å
Hall symbol: -P 2yc	Cell parameters from 3185 reflections
a = 13.496 (1) Å	θ = 2.1–27.4°
b = 4.931 (1) Å	µ = 1.67 mm⁻¹
c = 12.357 (1) Å	T = 293 K
β = 113.352 (1)°	Block, colourless
V = 755.0 (2) Å³	0.21 × 0.19 × 0.15 mm
Z = 2

Data collection top

Rigaku R-AXIS RAPID diffractometer	1696 independent reflections
Radiation source: fine-focus sealed tube	1461 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.027
Detector resolution: 10 pixels mm^-1	θ_max = 27.5°, θ_min = 3.3°
ω scans	h = −10→17
Absorption correction: multi-scan (ABSCOR; Higashi, 1995)	k = −6→5
T_min = 0.707, T_max = 0.780	l = −15→15
4318 measured reflections

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)] = 0.032	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.075	H atoms treated by a mixture of independent and constrained refinement
S = 1.06	w = 1/[σ²(F_o²) + (0.0304P)² + 0.2993P] where P = (F_o² + 2F_c²)/3
1696 reflections	(Δ/σ)_max < 0.001
118 parameters	Δρ_max = 0.25 e Å⁻³
0 restraints	Δρ_min = −0.30 e Å⁻³

Crystal data top

[Zn(C₁₅H₁₀O₆)(H₂O)₂]	V = 755.0 (2) Å³
M_r = 387.63	Z = 2
Monoclinic, P2/c	Mo Kα radiation
a = 13.496 (1) Å	µ = 1.67 mm⁻¹
b = 4.931 (1) Å	T = 293 K
c = 12.357 (1) Å	0.21 × 0.19 × 0.15 mm
β = 113.352 (1)°

Data collection top

Rigaku R-AXIS RAPID diffractometer	1696 independent reflections
Absorption correction: multi-scan (ABSCOR; Higashi, 1995)	1461 reflections with I > 2σ(I)
T_min = 0.707, T_max = 0.780	R_int = 0.027
4318 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.032	0 restraints
wR(F²) = 0.075	H atoms treated by a mixture of independent and constrained refinement
S = 1.06	Δρ_max = 0.25 e Å⁻³
1696 reflections	Δρ_min = −0.30 e Å⁻³
118 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	Occ. (<1)
Zn1	0.0000	0.02532 (7)	0.2500	0.03611 (14)
O3	0.48509 (13)	1.0388 (3)	0.65056 (14)	0.0430 (4)
O4	0.06484 (17)	−0.2446 (4)	0.17945 (17)	0.0484 (5)
O2	0.07014 (13)	0.2515 (3)	0.46679 (14)	0.0420 (4)
O1	0.12200 (13)	0.2746 (3)	0.31887 (13)	0.0406 (4)
C5	0.39531 (18)	0.8759 (5)	0.60267 (19)	0.0351 (5)
C7	0.22564 (18)	0.6856 (4)	0.58165 (19)	0.0356 (5)
H7	0.1685	0.6754	0.6055	0.043*
C1	0.13275 (18)	0.3401 (4)	0.42419 (18)	0.0331 (5)
C8	0.5000	1.1980 (7)	0.7500	0.0451 (8)
H8A	0.4375	1.3138	0.7330	0.054*	0.50
H8B	0.5625	1.3138	0.7670	0.054*	0.50
C2	0.22362 (18)	0.5269 (4)	0.48823 (19)	0.0328 (5)
C6	0.31099 (19)	0.8591 (5)	0.6403 (2)	0.0379 (5)
H6	0.3119	0.9624	0.7037	0.046*
C3	0.3096 (2)	0.5481 (5)	0.4528 (2)	0.0434 (6)
H3	0.3092	0.4453	0.3896	0.052*
C4	0.3942 (2)	0.7180 (5)	0.5100 (2)	0.0447 (6)
H4	0.4515	0.7273	0.4863	0.054*
H2	0.069 (3)	−0.244 (7)	0.110 (3)	0.100 (13)*
H1	0.085 (2)	−0.374 (6)	0.210 (2)	0.046 (8)*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Zn1	0.0455 (2)	0.0276 (2)	0.0380 (2)	0.000	0.01943 (18)	0.000
O3	0.0416 (9)	0.0491 (10)	0.0364 (9)	−0.0115 (8)	0.0132 (7)	0.0005 (7)
O4	0.0832 (14)	0.0311 (10)	0.0397 (10)	0.0128 (9)	0.0338 (10)	0.0040 (8)
O2	0.0471 (9)	0.0448 (9)	0.0359 (9)	−0.0096 (8)	0.0183 (7)	0.0003 (7)
O1	0.0538 (10)	0.0371 (9)	0.0338 (9)	−0.0057 (8)	0.0205 (8)	−0.0074 (7)
C5	0.0361 (12)	0.0332 (11)	0.0337 (12)	−0.0026 (10)	0.0114 (10)	0.0052 (10)
C7	0.0367 (12)	0.0370 (12)	0.0370 (12)	−0.0021 (10)	0.0189 (10)	−0.0009 (10)
C1	0.0404 (12)	0.0269 (10)	0.0293 (11)	0.0039 (9)	0.0110 (10)	0.0010 (9)
C8	0.045 (2)	0.0317 (17)	0.051 (2)	0.000	0.0109 (16)	0.000
C2	0.0379 (12)	0.0304 (11)	0.0301 (11)	−0.0009 (9)	0.0135 (9)	0.0015 (9)
C6	0.0445 (13)	0.0378 (12)	0.0338 (12)	−0.0033 (10)	0.0179 (11)	−0.0055 (10)
C3	0.0488 (14)	0.0483 (14)	0.0398 (13)	−0.0055 (12)	0.0246 (12)	−0.0078 (11)
C4	0.0447 (14)	0.0506 (14)	0.0483 (14)	−0.0037 (12)	0.0285 (12)	−0.0033 (12)

Geometric parameters (Å, º) top

Zn1—O1	1.9582 (18)	C7—C2	1.386 (3)
Zn1—O1ⁱ	1.9582 (18)	C7—C6	1.387 (3)
Zn1—O4	1.975 (2)	C7—H7	0.9300
Zn1—O4ⁱ	1.975 (2)	C1—C2	1.487 (3)
O3—C5	1.377 (3)	C8—O3ⁱⁱ	1.404 (2)
O3—C8	1.404 (2)	C8—H8A	0.9700
O4—H2	0.88 (4)	C8—H8B	0.9700
O4—H1	0.74 (3)	C2—C3	1.396 (3)
O2—C1	1.239 (3)	C6—H6	0.9300
O1—C1	1.292 (3)	C3—C4	1.366 (3)
C5—C4	1.380 (3)	C3—H3	0.9300
C5—C6	1.392 (3)	C4—H4	0.9300

O1—Zn1—O1ⁱ	102.26 (11)	O1—C1—C2	115.52 (19)
O1—Zn1—O4	99.87 (9)	O3—C8—O3ⁱⁱ	112.0 (3)
O1ⁱ—Zn1—O4	132.40 (8)	O3—C8—H8A	109.2
O1—Zn1—O4ⁱ	132.40 (8)	O3ⁱⁱ—C8—H8A	109.2
O1ⁱ—Zn1—O4ⁱ	99.87 (9)	O3—C8—H8B	109.2
O4—Zn1—O4ⁱ	95.27 (13)	O3ⁱⁱ—C8—H8B	109.2
C5—O3—C8	119.93 (16)	H8A—C8—H8B	107.9
Zn1—O4—H2	130 (2)	C7—C2—C3	118.3 (2)
Zn1—O4—H1	119 (2)	C7—C2—C1	122.2 (2)
H2—O4—H1	111 (3)	C3—C2—C1	119.5 (2)
C1—O1—Zn1	109.52 (14)	C7—C6—C5	118.8 (2)
O3—C5—C4	113.8 (2)	C7—C6—H6	120.6
O3—C5—C6	126.0 (2)	C5—C6—H6	120.6
C4—C5—C6	120.2 (2)	C4—C3—C2	120.8 (2)
C2—C7—C6	121.5 (2)	C4—C3—H3	119.6
C2—C7—H7	119.3	C2—C3—H3	119.6
C6—C7—H7	119.3	C3—C4—C5	120.4 (2)
O2—C1—O1	121.1 (2)	C3—C4—H4	119.8
O2—C1—C2	123.4 (2)	C5—C4—H4	119.8

O1ⁱ—Zn1—O1—C1	86.84 (14)	O1—C1—C2—C7	158.0 (2)
O4—Zn1—O1—C1	−135.58 (15)	O2—C1—C2—C3	159.3 (2)
O4ⁱ—Zn1—O1—C1	−29.01 (18)	O1—C1—C2—C3	−21.1 (3)
C8—O3—C5—C4	−176.2 (2)	C2—C7—C6—C5	1.0 (3)
C8—O3—C5—C6	3.1 (3)	O3—C5—C6—C7	179.5 (2)
Zn1—O1—C1—O2	−1.0 (3)	C4—C5—C6—C7	−1.2 (3)
Zn1—O1—C1—C2	179.28 (14)	C7—C2—C3—C4	0.9 (4)
C5—O3—C8—O3ⁱⁱ	64.94 (16)	C1—C2—C3—C4	−180.0 (2)
C6—C7—C2—C3	−0.9 (3)	C2—C3—C4—C5	−1.2 (4)
C6—C7—C2—C1	−179.9 (2)	O3—C5—C4—C3	−179.3 (2)
O2—C1—C2—C7	−21.7 (3)	C6—C5—C4—C3	1.3 (4)

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

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O4—H1···O1ⁱⁱⁱ	0.74 (3)	2.13 (3)	2.851 (3)	167 (3)
O4—H2···O2^iv	0.88 (4)	1.78 (4)	2.657 (3)	177 (4)
C8—H8A···Cg3^v	0.97	2.97	3.741 (3)	137
C8—H8B···Cg3^vi	0.97	2.97	3.741 (3)	137

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

Experimental details

Crystal data
Chemical formula	[Zn(C₁₅H₁₀O₆)(H₂O)₂]
M_r	387.63
Crystal system, space group	Monoclinic, P2/c
Temperature (K)	293
a, b, c (Å)	13.496 (1), 4.931 (1), 12.357 (1)
β (°)	113.352 (1)
V (Å³)	755.0 (2)
Z	2
Radiation type	Mo Kα
µ (mm⁻¹)	1.67
Crystal size (mm)	0.21 × 0.19 × 0.15

Data collection
Diffractometer	Rigaku R-AXIS RAPID diffractometer
Absorption correction	Multi-scan (ABSCOR; Higashi, 1995)
T_min, T_max	0.707, 0.780
No. of measured, independent and observed [I > 2σ(I)] reflections	4318, 1696, 1461
R_int	0.027
(sin θ/λ)_max (Å⁻¹)	0.649

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.032, 0.075, 1.06
No. of reflections	1696
No. of parameters	118
H-atom treatment	H atoms treated by a mixture of independent and constrained refinement
Δρ_max, Δρ_min (e Å⁻³)	0.25, −0.30

Computer programs: PROCESS-AUTO (Rigaku, 1998), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), SHELXTL-Plus (Sheldrick, 2008).

Selected geometric parameters (Å, º) top

Zn1—O1	1.9582 (18)	Zn1—O4	1.975 (2)

O1—Zn1—O1ⁱ	102.26 (11)	O1ⁱ—Zn1—O4	132.40 (8)
O1—Zn1—O4	99.87 (9)	O4—Zn1—O4ⁱ	95.27 (13)

Symmetry code: (i) −x, y, −z+1/2.

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O4—H1···O1ⁱⁱ	0.74 (3)	2.13 (3)	2.851 (3)	167 (3)
O4—H2···O2ⁱⁱⁱ	0.88 (4)	1.78 (4)	2.657 (3)	177 (4)
C8—H8A···Cg3^iv	0.97	2.97	3.741 (3)	137
C8—H8B···Cg3^v	0.97	2.97	3.741 (3)	137

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

Acknowledgements

The authors thank the the National Natural Science Foundation of China (No. 50878041) and the Analysis and Testing Foundation of Northeast Normal University for financial support.

References

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