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Acta Cryst. (2009). E65, m509    [ doi:10.1107/S1600536809012604 ]

catena-Poly[[diaquazinc(II)]-[mu]-trans-4,4'-diazenediyldibenzoato-[kappa]4O,O':O'',O''']

B. Liu and Q. Xu

Abstract top

The title compound, [Zn(C14H8N2O4)(H2O)2]n, consists of zigzag chains of Zn atoms bridged by azobenzene-4,4'-dicarboxylate ligands. The ZnII 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, [pi]-[pi] 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.

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 Oaq···Ocarboxylate 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.

Refinement top

Aromatic H atoms were positioned geometrically and refined as riding, with C—H = 0.93 Å and with Uiso(H) = 1.2Ueq(C). H atoms of water molecule were located on a difference Fourier map. One (H3A) of the two water H atoms was fixed with O—H = 0.82 Å and Uiso(H) = 1.5Ueq(O). The other H atom (H3B) was refined isotropically, with a distance restraint O—H = 0.82 (1) Å. In the final difference map, the highest peak and deepest hole were found to be 0.81 and 0.60 Å from N1 atom, respectively.

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
[Figure 1] 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.]
[Figure 2] 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
Mr = 369.63Dx = 1.825 Mg m−3
Monoclinic, C2/cMo Kα radiation, λ = 0.71073 Å
Hall symbol: -C 2ycCell parameters from 1194 reflections
a = 22.392 (5) Åθ = 3.3–27.5°
b = 4.9308 (10) ŵ = 1.86 mm−1
c = 12.185 (2) ÅT = 293 K
β = 90.30 (3)°Needle, orange
V = 1345.3 (5) Å30.14 × 0.09 × 0.08 mm
Z = 4
Data collection top
Rigaku R-AXIS RAPID
diffractometer		1532 independent reflections
Radiation source: rotating anode1194 reflections with I > 2σ(I)
graphiteRint = 0.043
ω scansθmax = 27.5°, θmin = 3.3°
Absorption correction: multi-scan
(ABSCOR; Higashi, 1995)		h = −28→28
Tmin = 0.781, Tmax = 0.865k = −6→6
6205 measured reflectionsl = −14→15
Refinement top
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.044Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.109H atoms treated by a mixture of independent and constrained refinement
S = 1.04 w = 1/[σ2(Fo2) + (0.0399P)2 + 7.8756P]
where P = (Fo2 + 2Fc2)/3
1532 reflections(Δ/σ)max < 0.001
110 parametersΔρmax = 1.37 e Å−3
8 restraintsΔρmin = −0.89 e Å−3
Crystal data top
[Zn(C14H8N2O4)(H2O)2]V = 1345.3 (5) Å3
Mr = 369.63Z = 4
Monoclinic, C2/cMo Kα radiation
a = 22.392 (5) ŵ = 1.86 mm−1
b = 4.9308 (10) ÅT = 293 K
c = 12.185 (2) Å0.14 × 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)
Tmin = 0.781, Tmax = 0.865Rint = 0.043
6205 measured reflectionsθmax = 27.5°
Refinement top
R[F2 > 2σ(F2)] = 0.044H atoms treated by a mixture of independent and constrained refinement
wR(F2) = 0.109Δρmax = 1.37 e Å−3
S = 1.04Δρmin = −0.89 e Å−3
1532 reflectionsAbsolute structure: ?
110 parametersFlack parameter: ?
8 restraintsRogers parameter: ?
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
Zn10.00000.08046 (11)0.75000.0287 (2)
O10.06809 (11)0.3407 (5)0.7428 (2)0.0270 (6)
O20.04382 (12)0.2669 (5)0.5705 (2)0.0343 (6)
C10.07463 (15)0.3874 (7)0.6402 (3)0.0233 (7)
O3−0.03292 (14)−0.2000 (5)0.6496 (2)0.0364 (7)
H3A−0.0458−0.32740.68570.055*
C20.12028 (14)0.5963 (7)0.6090 (3)0.0229 (7)
C60.16404 (19)0.9039 (8)0.4779 (4)0.0401 (10)
H60.16510.97680.40750.048*
C50.20375 (18)0.9943 (8)0.5579 (4)0.0399 (7)
C70.12236 (18)0.7023 (8)0.5038 (3)0.0332 (8)
H70.09600.63940.45030.040*
C30.16064 (17)0.6897 (8)0.6873 (3)0.0323 (8)
H30.15990.61790.75780.039*
C40.20196 (18)0.8879 (8)0.6617 (4)0.0399 (10)
H40.22860.94920.71500.048*
H3B−0.037 (2)−0.207 (12)0.584 (5)0.068 (18)*
N10.25044 (16)1.2046 (7)0.5460 (3)0.0415 (7)
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Zn10.0257 (3)0.0176 (3)0.0429 (4)0.0000.0010 (2)0.000
O10.0319 (14)0.0247 (12)0.0244 (13)−0.0017 (10)0.0061 (10)0.0034 (10)
O20.0348 (15)0.0331 (14)0.0351 (15)−0.0108 (12)0.0020 (12)−0.0059 (12)
C10.0230 (16)0.0196 (16)0.0274 (18)0.0033 (13)0.0045 (13)−0.0015 (14)
O30.059 (2)0.0231 (13)0.0273 (16)−0.0099 (13)0.0025 (14)0.0009 (11)
C20.0223 (16)0.0206 (15)0.0258 (17)−0.0011 (13)0.0080 (13)−0.0001 (14)
C60.045 (2)0.035 (2)0.041 (2)0.0047 (19)0.0167 (19)0.0171 (19)
C50.0342 (15)0.0342 (15)0.0513 (18)0.0033 (13)0.0110 (14)0.0006 (14)
C70.038 (2)0.034 (2)0.028 (2)−0.0023 (17)0.0022 (16)0.0028 (16)
C30.0288 (19)0.0323 (19)0.036 (2)−0.0057 (15)0.0039 (16)−0.0006 (17)
C40.0274 (19)0.037 (2)0.056 (3)−0.0095 (17)0.0043 (18)−0.0082 (19)
N10.0368 (15)0.0375 (15)0.0505 (17)0.0050 (13)0.0094 (14)0.0012 (13)
Geometric parameters (Å, °) top
Zn1—O31.985 (3)C2—C31.389 (5)
Zn1—O3i1.985 (3)C6—C51.389 (6)
Zn1—O22.572 (2)C6—C71.401 (5)
Zn1—O11.995 (2)C6—H60.9300
Zn1—O1i1.995 (2)C5—C41.371 (6)
O1—C11.280 (4)C5—N11.480 (5)
O2—C11.243 (4)C7—H70.9300
C1—C21.501 (5)C3—C41.383 (5)
O3—H3A0.8200C3—H30.9300
O3—H3B0.81 (6)C4—H40.9300
C2—C71.385 (5)N1—N1ii1.207 (7)
O3—Zn1—O3i91.71 (17)C5—C6—C7119.6 (4)
O3—Zn1—O1134.60 (11)C5—C6—H6120.2
O3i—Zn1—O1101.17 (12)C7—C6—H6120.2
O3—Zn1—O1i101.17 (12)C4—C5—C6120.2 (4)
O3i—Zn1—O1i134.60 (11)C4—C5—N1112.5 (4)
O1—Zn1—O1i99.95 (15)C6—C5—N1127.3 (4)
C1—O1—Zn1104.5 (2)C2—C7—C6120.2 (4)
C1—O2—Zn178.6 (2)C2—C7—H7119.9
O2—C1—O1121.0 (3)C6—C7—H7119.9
O2—C1—C2122.1 (3)C4—C3—C2120.9 (4)
O1—C1—C2116.9 (3)C4—C3—H3119.6
Zn1—O3—H3A109.5C2—C3—H3119.6
Zn1—O3—H3B133 (4)C5—C4—C3120.1 (4)
H3A—O3—H3B117.4C5—C4—H4120.0
C7—C2—C3119.0 (3)C3—C4—H4120.0
C7—C2—C1121.3 (3)N1ii—N1—C5110.0 (5)
C3—C2—C1119.7 (3)
O3—Zn1—O1—C128.2 (3)C3—C2—C7—C6−1.1 (6)
O3i—Zn1—O1—C1131.9 (2)C1—C2—C7—C6177.8 (3)
O1i—Zn1—O1—C1−88.5 (2)C5—C6—C7—C20.8 (6)
Zn1—O1—C1—O2−3.7 (4)C7—C2—C3—C40.8 (6)
Zn1—O1—C1—C2175.3 (2)C1—C2—C3—C4−178.0 (3)
O2—C1—C2—C712.6 (5)C6—C5—C4—C30.1 (6)
O1—C1—C2—C7−166.5 (3)N1—C5—C4—C3179.6 (4)
O2—C1—C2—C3−168.6 (3)C2—C3—C4—C5−0.4 (6)
O1—C1—C2—C312.3 (5)C4—C5—N1—N1ii−178.8 (4)
C7—C6—C5—C4−0.3 (6)C6—C5—N1—N1ii0.7 (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, °) top
D—H···AD—HH···AD···AD—H···A
O3—H3A···O1iii0.821.922.735 (4)171
O3—H3B···O2iv0.81 (6)1.91 (6)2.712 (4)173 (6)
Symmetry codes: (iii) −x, y−1, −z+3/2; (iv) −x, −y, −z+1.
Table 1
Selected geometric parameters (Å) top
Zn1—O31.985 (3)Zn1—O11.995 (2)
Zn1—O22.572 (2)
Table 2
Hydrogen-bond geometry (Å, °) top
D—H···AD—HH···AD···AD—H···A
O3—H3A···O1i0.821.922.735 (4)171
O3—H3B···O2ii0.81 (6)1.91 (6)2.712 (4)173 (6)
Symmetry codes: (i) −x, y−1, −z+3/2; (ii) −x, −y, −z+1.
Acknowledgements top

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

references
References top

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