catena-Poly[[diaquazinc(II)]-μ-trans-4,4′-diazenediyldibenzoato-κ4O,O′:O′′,O′′′]

Liu, B.; Xu, Q.

doi:10.1107/S1600536809012604

metal-organic compounds

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ISSN: 2056-9890

Volume 65| Part 5| May 2009| Page m509

doi:10.1107/S1600536809012604

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catena-Poly[[diaquazinc(II)]-μ-trans-4,4′-diazenediyldibenzoato-κ⁴O,O′:O′′,O′′′]

Bo Liu ^a and Qiang Xu ^a ^*

^aNational Institute of Advanced Industrial Science and Technology (AIST), Ikeda, Osaka 563-8577, Japan, and Graduate School of Science and Technology, Kobe University, Nada Ku, Kobe, Hyogo 657-8501, Japan
^*Correspondence e-mail: q.xu@aist.go.jp

(Received 27 February 2009; accepted 3 April 2009; online 10 April 2009)

The title compound, [Zn(C₁₄H₈N₂O₄)(H₂O)₂]_n, consists of zigzag chains of Zn atoms bridged by azobenzene-4,4′-dicarboxylate ligands. The Zn^II atom, lying on a twofold rotation axis, is coordinated by four O atoms from the carboxylate groups and two water molecules, giving rise to a considerably distorted octahedral coordination envionment. The ligand lies on an inversion center. In the crystal structure, π–π interactions between the ligands [interplanar distance = 3.527 (3) Å] assemble the chains into a sheet-like structure. O—H⋯O hydrogen bonds between the coordinated water molecules and carboxylate O atoms connect the sheets into a three-dimensional network.

Related literature

For related structures, see: Chen et al. (2008 ); Bai et al. (2008 ); Mukherjee et al. (2004 ); Reineke et al. (2000 ).

Experimental

Crystal data

[Zn(C₁₄H₈N₂O₄)(H₂O)₂]
M_r = 369.63
Monoclinic, C 2/c
a = 22.392 (5) Å
b = 4.9308 (10) Å
c = 12.185 (2) Å
β = 90.30 (3)°
V = 1345.3 (5) Å³
Z = 4
Mo Kα radiation
μ = 1.86 mm⁻¹
T = 293 K
0.14 × 0.09 × 0.08 mm

Data collection

Rigaku R-AXIS RAPID diffractometer
Absorption correction: multi-scan (ABSCOR; Higashi, 1995 ) T_min = 0.781, T_max = 0.865
6205 measured reflections
1532 independent reflections
1194 reflections with I > 2σ(I)
R_int = 0.043

Refinement

R[F² > 2σ(F²)] = 0.044
wR(F²) = 0.109
S = 1.04
1532 reflections
110 parameters
8 restraints
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 1.37 e Å⁻³
Δρ_min = −0.89 e Å⁻³

Table 1
Selected bond lengths (Å)

Zn1—O3	1.985 (3)
Zn1—O2	2.572 (2)
Zn1—O1	1.995 (2)

Table 2
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O3—H3A⋯O1ⁱ	0.82	1.92	2.735 (4)	171
O3—H3B⋯O2ⁱⁱ	0.81 (6)	1.91 (6)	2.712 (4)	173 (6)
Symmetry codes: (i) $[-x, y-1, -z+{\script{3\over 2}}]$ ; (ii) -x, -y, -z+1.

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: Mercury (Macrae et al., 2006 ); software used to prepare material for publication: publCIF (Westrip, 2009 ).

Supporting information

Crystal structure: contains datablocks I, New_Global_Publ_Block. DOI: 10.1107/S1600536809012604/hy2186sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536809012604/hy2186Isup2.hkl

checkCIF report

Comment top

Metal-organic frameworks, in which metal ions are bridged by organic ligands, have a rapid development in the past decade due to the various topologies and wide applications. Azodibenzoate-based ligands are a kind of typical aromatic carboxylate ligand employed in the generation of coordination networks, including azobenzene-4,4'-dicarboxylate and azobenzene-3,3'-dicarboxylate and so on. A series of coordination polymers have been reported by employing these ligands as linkers (Chen et al., 2008; Bai et al., 2008; Mukherjee et al., 2004; Reineke et al., 2000). The title compound (Fig. 1 and Table 1) is an analogue to the reported compound [Cd(C₁₄H₈N₂O₄)(H₂O)₂]_n (Chen et al., 2008). The space group of the reported Cd complex is P2₁/m, while that of the title compound is determined to be C2/c. The seperation between the bridged Zn atoms is 17.211 (1) Å and the angle for the three neighboring Zn atoms is 95.84 (8)°. In comparison, the O_aq···O_carboxylate distances for hydrogen bonds are 2.712 (4) and 2.735 (4) Å in the title compound (Table 2), while they are greater than 3.19 Å in the Cd complex. Face-to-face π–π interaction between the ligands exists in the title compound [interplane distance = 3.527 (3) Å], which assembles the Zn–ligand chains into a sheet. O—H···O hydrogen bonds between the coordinated water molecules and carboxylate O atoms connect the sheets into a three-dimensional network (Fig. 2).

Related literature top

For related structures, see: Chen et al. (2008); Bai et al. (2008); Mukherjee et al. (2004); Reineke et al. (2000).

Experimental top

The single crystals of the title compound were obtained by solvothermal reaction of Zn(NO₃)₂.6H₂O (0.013 g) and azobenzene-4,4'-dicarboxylic acid (0.007 g) in a mixed solvent of DMSO and H₂O (20 ml, volume ratio 1:1) at 393 K for 72 h.

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: Mercury (Macrae et al., 2006); software used to prepare material for publication: publCIF (Westrip, 2009).

Figures top

	Fig. 1. Part of the chain in the title compound. Displacement ellipsoids are drawn at the 50% probability level. H atoms have been omitted for clarity. [Symmetry codes: (iii) -x, y, 3/2 - z; (iv) 1/2 - x, 5/2 - y, 1 - z.]
	Fig. 2. The crystal packing diagram showing hydrogen bonds (dashed lines).

catena-Poly[[diaquazinc(II)]-µ-trans-4,4'- diazenediyldibenzoato-κ⁴O,O':O'',O'''] top

Crystal data top

[Zn(C₁₄H₈N₂O₄)(H₂O)₂]	F(000) = 752
M_r = 369.63	D_x = 1.825 Mg m⁻³
Monoclinic, C2/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -C 2yc	Cell parameters from 1194 reflections
a = 22.392 (5) Å	θ = 3.3–27.5°
b = 4.9308 (10) Å	µ = 1.86 mm⁻¹
c = 12.185 (2) Å	T = 293 K
β = 90.30 (3)°	Needle, orange
V = 1345.3 (5) Å³	0.14 × 0.09 × 0.08 mm
Z = 4

Data collection top

Rigaku R-AXIS RAPID diffractometer	1532 independent reflections
Radiation source: rotating anode	1194 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.043
ω scans	θ_max = 27.5°, θ_min = 3.3°
Absorption correction: multi-scan (ABSCOR; Higashi, 1995)	h = −28→28
T_min = 0.781, T_max = 0.865	k = −6→6
6205 measured reflections	l = −14→15

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)] = 0.044	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.109	H atoms treated by a mixture of independent and constrained refinement
S = 1.04	w = 1/[σ²(F_o²) + (0.0399P)² + 7.8756P] where P = (F_o² + 2F_c²)/3
1532 reflections	(Δ/σ)_max < 0.001
110 parameters	Δρ_max = 1.37 e Å⁻³
8 restraints	Δρ_min = −0.89 e Å⁻³

Crystal data top

[Zn(C₁₄H₈N₂O₄)(H₂O)₂]	V = 1345.3 (5) Å³
M_r = 369.63	Z = 4
Monoclinic, C2/c	Mo Kα radiation
a = 22.392 (5) Å	µ = 1.86 mm⁻¹
b = 4.9308 (10) Å	T = 293 K
c = 12.185 (2) Å	0.14 × 0.09 × 0.08 mm
β = 90.30 (3)°

Data collection top

Rigaku R-AXIS RAPID diffractometer	1532 independent reflections
Absorption correction: multi-scan (ABSCOR; Higashi, 1995)	1194 reflections with I > 2σ(I)
T_min = 0.781, T_max = 0.865	R_int = 0.043
6205 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.044	8 restraints
wR(F²) = 0.109	H atoms treated by a mixture of independent and constrained refinement
S = 1.04	Δρ_max = 1.37 e Å⁻³
1532 reflections	Δρ_min = −0.89 e Å⁻³
110 parameters

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å²) top

	x	y	z	U_iso*/U_eq
Zn1	0.0000	0.08046 (11)	0.7500	0.0287 (2)
O1	0.06809 (11)	0.3407 (5)	0.7428 (2)	0.0270 (6)
O2	0.04382 (12)	0.2669 (5)	0.5705 (2)	0.0343 (6)
C1	0.07463 (15)	0.3874 (7)	0.6402 (3)	0.0233 (7)
O3	−0.03292 (14)	−0.2000 (5)	0.6496 (2)	0.0364 (7)
H3A	−0.0458	−0.3274	0.6857	0.055*
C2	0.12028 (14)	0.5963 (7)	0.6090 (3)	0.0229 (7)
C6	0.16404 (19)	0.9039 (8)	0.4779 (4)	0.0401 (10)
H6	0.1651	0.9768	0.4075	0.048*
C5	0.20375 (18)	0.9943 (8)	0.5579 (4)	0.0399 (7)
C7	0.12236 (18)	0.7023 (8)	0.5038 (3)	0.0332 (8)
H7	0.0960	0.6394	0.4503	0.040*
C3	0.16064 (17)	0.6897 (8)	0.6873 (3)	0.0323 (8)
H3	0.1599	0.6179	0.7578	0.039*
C4	0.20196 (18)	0.8879 (8)	0.6617 (4)	0.0399 (10)
H4	0.2286	0.9492	0.7150	0.048*
H3B	−0.037 (2)	−0.207 (12)	0.584 (5)	0.068 (18)*
N1	0.25044 (16)	1.2046 (7)	0.5460 (3)	0.0415 (7)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Zn1	0.0257 (3)	0.0176 (3)	0.0429 (4)	0.000	0.0010 (2)	0.000
O1	0.0319 (14)	0.0247 (12)	0.0244 (13)	−0.0017 (10)	0.0061 (10)	0.0034 (10)
O2	0.0348 (15)	0.0331 (14)	0.0351 (15)	−0.0108 (12)	0.0020 (12)	−0.0059 (12)
C1	0.0230 (16)	0.0196 (16)	0.0274 (18)	0.0033 (13)	0.0045 (13)	−0.0015 (14)
O3	0.059 (2)	0.0231 (13)	0.0273 (16)	−0.0099 (13)	0.0025 (14)	0.0009 (11)
C2	0.0223 (16)	0.0206 (15)	0.0258 (17)	−0.0011 (13)	0.0080 (13)	−0.0001 (14)
C6	0.045 (2)	0.035 (2)	0.041 (2)	0.0047 (19)	0.0167 (19)	0.0171 (19)
C5	0.0342 (15)	0.0342 (15)	0.0513 (18)	0.0033 (13)	0.0110 (14)	0.0006 (14)
C7	0.038 (2)	0.034 (2)	0.028 (2)	−0.0023 (17)	0.0022 (16)	0.0028 (16)
C3	0.0288 (19)	0.0323 (19)	0.036 (2)	−0.0057 (15)	0.0039 (16)	−0.0006 (17)
C4	0.0274 (19)	0.037 (2)	0.056 (3)	−0.0095 (17)	0.0043 (18)	−0.0082 (19)
N1	0.0368 (15)	0.0375 (15)	0.0505 (17)	0.0050 (13)	0.0094 (14)	0.0012 (13)

Geometric parameters (Å, º) top

Zn1—O3	1.985 (3)	C2—C3	1.389 (5)
Zn1—O3ⁱ	1.985 (3)	C6—C5	1.389 (6)
Zn1—O2	2.572 (2)	C6—C7	1.401 (5)
Zn1—O1	1.995 (2)	C6—H6	0.9300
Zn1—O1ⁱ	1.995 (2)	C5—C4	1.371 (6)
O1—C1	1.280 (4)	C5—N1	1.480 (5)
O2—C1	1.243 (4)	C7—H7	0.9300
C1—C2	1.501 (5)	C3—C4	1.383 (5)
O3—H3A	0.8200	C3—H3	0.9300
O3—H3B	0.81 (6)	C4—H4	0.9300
C2—C7	1.385 (5)	N1—N1ⁱⁱ	1.207 (7)

O3—Zn1—O3ⁱ	91.71 (17)	C5—C6—C7	119.6 (4)
O3—Zn1—O1	134.60 (11)	C5—C6—H6	120.2
O3ⁱ—Zn1—O1	101.17 (12)	C7—C6—H6	120.2
O3—Zn1—O1ⁱ	101.17 (12)	C4—C5—C6	120.2 (4)
O3ⁱ—Zn1—O1ⁱ	134.60 (11)	C4—C5—N1	112.5 (4)
O1—Zn1—O1ⁱ	99.95 (15)	C6—C5—N1	127.3 (4)
C1—O1—Zn1	104.5 (2)	C2—C7—C6	120.2 (4)
C1—O2—Zn1	78.6 (2)	C2—C7—H7	119.9
O2—C1—O1	121.0 (3)	C6—C7—H7	119.9
O2—C1—C2	122.1 (3)	C4—C3—C2	120.9 (4)
O1—C1—C2	116.9 (3)	C4—C3—H3	119.6
Zn1—O3—H3A	109.5	C2—C3—H3	119.6
Zn1—O3—H3B	133 (4)	C5—C4—C3	120.1 (4)
H3A—O3—H3B	117.4	C5—C4—H4	120.0
C7—C2—C3	119.0 (3)	C3—C4—H4	120.0
C7—C2—C1	121.3 (3)	N1ⁱⁱ—N1—C5	110.0 (5)
C3—C2—C1	119.7 (3)

O3—Zn1—O1—C1	28.2 (3)	C3—C2—C7—C6	−1.1 (6)
O3ⁱ—Zn1—O1—C1	131.9 (2)	C1—C2—C7—C6	177.8 (3)
O1ⁱ—Zn1—O1—C1	−88.5 (2)	C5—C6—C7—C2	0.8 (6)
Zn1—O1—C1—O2	−3.7 (4)	C7—C2—C3—C4	0.8 (6)
Zn1—O1—C1—C2	175.3 (2)	C1—C2—C3—C4	−178.0 (3)
O2—C1—C2—C7	12.6 (5)	C6—C5—C4—C3	0.1 (6)
O1—C1—C2—C7	−166.5 (3)	N1—C5—C4—C3	179.6 (4)
O2—C1—C2—C3	−168.6 (3)	C2—C3—C4—C5	−0.4 (6)
O1—C1—C2—C3	12.3 (5)	C4—C5—N1—N1ⁱⁱ	−178.8 (4)
C7—C6—C5—C4	−0.3 (6)	C6—C5—N1—N1ⁱⁱ	0.7 (7)
C7—C6—C5—N1	−179.8 (4)

Symmetry codes: (i) −x, y, −z+3/2; (ii) −x+1/2, −y+5/2, −z+1.

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O3—H3A···O1ⁱⁱⁱ	0.82	1.92	2.735 (4)	171
O3—H3B···O2^iv	0.81 (6)	1.91 (6)	2.712 (4)	173 (6)

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

Experimental details

Crystal data
Chemical formula	[Zn(C₁₄H₈N₂O₄)(H₂O)₂]
M_r	369.63
Crystal system, space group	Monoclinic, C2/c
Temperature (K)	293
a, b, c (Å)	22.392 (5), 4.9308 (10), 12.185 (2)
β (°)	90.30 (3)
V (Å³)	1345.3 (5)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	1.86
Crystal size (mm)	0.14 × 0.09 × 0.08

Data collection
Diffractometer	Rigaku R-AXIS RAPID diffractometer
Absorption correction	Multi-scan (ABSCOR; Higashi, 1995)
T_min, T_max	0.781, 0.865
No. of measured, independent and observed [I > 2σ(I)] reflections	6205, 1532, 1194
R_int	0.043
(sin θ/λ)_max (Å⁻¹)	0.649

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.044, 0.109, 1.04
No. of reflections	1532
No. of parameters	110
No. of restraints	8
H-atom treatment	H atoms treated by a mixture of independent and constrained refinement
Δρ_max, Δρ_min (e Å⁻³)	1.37, −0.89

Computer programs: PROCESS-AUTO (Rigaku, 1998), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), Mercury (Macrae et al., 2006), publCIF (Westrip, 2009).

Selected bond lengths (Å) top

Zn1—O3	1.985 (3)	Zn1—O1	1.995 (2)
Zn1—O2	2.572 (2)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O3—H3A···O1ⁱ	0.82	1.92	2.735 (4)	171
O3—H3B···O2ⁱⁱ	0.81 (6)	1.91 (6)	2.712 (4)	173 (6)

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

Acknowledgements

We thank AIST and Kobe University for financial support. BL thanks MEXT for a Japanese Government Scholarship.

References

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