metal-organic compounds\(\def\hfill{\hskip 5em}\def\hfil{\hskip 3em}\def\eqno#1{\hfil {#1}}\)

Journal logoSTRUCTURAL
CHEMISTRY
ISSN: 2053-2296

Poly[aqua­[μ4-3,3′-(diazenediyl)dibenzo­ato]zinc]

aCollege of Chemistry and Chemical Engineering, Anyang Normal University, Anyang 455000, Henan, People's Republic of China
*Correspondence e-mail: liuleileimail@163.com

(Received 29 October 2012; accepted 29 November 2012; online 13 December 2012)

The solvothermal reaction of Zn(OAc)2·2H2O with 3,3′-(di­az­enediyl)dibenzoic acid (H2ADB) in H2O at 393 K afforded the title complex, [Zn(C14H8N2O4)(H2O)]n. The asymmetric unit contains half a ZnII cation, half an ADB ligand and half a water mol­ecule. Each ZnII centre lies on a crystallographic twofold rotation axis and is five-coordinated by four O atoms of bridging carboxyl­ate groups from four ADB ligands and one O atom from a water mol­ecule, forming a distorted trigonal–bipyramidal coordination geometry. The [Zn(H2O)] subunits are bridged by carboxyl­ate groups to give one-dimensional [Zn(μ-COO)4(H2O)]n chains. The chains are linked by ADB ligands into two-dimensional sheets, and these sheets are further connected to neighbouring sheets via hydrogen bonds (OW—HW⋯O), forming a three-dimensional hydrogen-bond-stabilized structure with an unprecedented 374175262 topology.

Comment

In recent years, azobenzoic acid derivatives such as azobenzene­dicarb­oxy­lic, azobenzene­tricarb­oxy­lic and azobenzene­tetra­carb­oxy­lic acids have been employed as bridging ligands for constructing various types of functional metal–organic frameworks (MOFs) (Cairns et al., 2008[Cairns, A. J., Perman, J. A., Wojtas, L., Kravtsov, V. C., Alkordi, M. H., Eddaoudi, M. & Zaworotko, M. J. (2008). J. Am. Chem. Soc. 130, 1560-1561.]; Lee et al., 2008[Lee, Y.-G., Moon, H.-R., Cheon, Y.-E. & Suh, M.-P. (2008). Angew. Chem. Int. Ed. 47, 7741-7745.]; Bhattacharya et al., 2011[Bhattacharya, S., Sanyal, U. & Natarajan, S. (2011). Cryst. Growth Des. 11, 735-747.]; Yang et al., 2011[Yang, J., Ma, J.-F., Batten, S. R., Ng, S. W. & Liu, Y.-Y. (2011). CrystEngComm, 13, 5296-5298.]; Liu, Ren et al., 2011[Liu, L.-L., Ren, Z.-G., Zhu, L.-W., Wang, H.-F., Yan, W.-Y. & Lang, J.-P. (2011). Cryst. Growth Des. 11, 3479-3488.]; Liu, Wan et al., 2011[Liu, L.-L., Wan, L.-M., Ren, Z.-G. & Lang, J.-P. (2011). Inorg. Chem. Commun. 14, 1069-1072.]; Liu & Xu, 2009[Liu, B. & Xu, Q. (2009). Acta Cryst. E65, m509.]). For example, Yaghi and co-workers used 4,4′-azodibenzoic acid (4,4′-H2ADB) reacted with Tb(NO3)3·5H2O to form an inter­penetrating network of {Tb2(ADB)3[(CH3)2SO]4·16[(CH3)2SO]}n with a large free volume (Reineke et al., 2000[Reineke, T. M., Eddaoudi, M., Moler, D., O'Keeffe, M. & Yaghi, O. M. (2000). J. Am. Chem. Soc. 122, 4843-4844.]). Recently, Lu and co-workers reported three porous MOFs constructed from azobenzene-3,5,4′-tricarb­oxy­lic acid (H3ABTC) and Cd(NO3)2·4H2O or MnCl2·4H2O (Meng et al., 2011[Meng, M., Zhong, D.-C. & Lu, T.-B. (2011). CrystEngComm, 13, 6794-6800.]). Qiu and co-workers used 3,3′,5,5′-azobenzene­tetra­carb­oxy­lic acid (H4ABTC) to construct three three-dimensional microporous MOFs with NbO and PtS topologies, which show hydrogen storage and luminescent properties (Xue et al., 2008[Xue, M., Zhu, G.-S., Li, Y.-X., Zhao, X.-J., Jin, Z., Kang, E.-H. & Qiu, S.-L. (2008). Cryst. Growth Des. 8, 2478-2483.]). As for 3,3′-(diazenedi­yl)dibenzoic acid (H2ADB), Cudic et al. (1999[Cudic, P., Vigneron, J. P., Lehn, J. M., Cesario, M. & Prange, T. (1999). Eur. J. Org. Chem. 10, 2479-2484.]) studied the host–guest chemistry between cyclo-bis-inter­caland and ADB, and recently Chen et al. (2008[Chen, Z.-F., Zhang, Z.-L., Tan, Y.-H., Tang, Y.-Z., Fun, H.-K., Zhou, Z.-Y., Abrahams, B. F. & Liang, H. (2008). CrystEngComm, 10, 217-231.]) reported seven coordination polymers based on the assembly of H2ADB with Zn(OAc)2, PbI2, Co(OAc)2, Y(OAc)3, Sm(OAc)3 or Er(OAc)3, and/or 1,10-phenanthroline, which displayed considerable structural variety. Chen's ZnII ADB coordination polymer, [Zn(ADB)(EtOH)]n, was synthesized from Zn(OAc)2, pyridine and H2ADB in a mixture of solvents (DMF/H2O/EtOH) and shows a two-dimensional (4,4) network with Zn2 units serving as four-connecting square nodes (Chen et al., 2008[Chen, Z.-F., Zhang, Z.-L., Tan, Y.-H., Tang, Y.-Z., Fun, H.-K., Zhou, Z.-Y., Abrahams, B. F. & Liang, H. (2008). CrystEngComm, 10, 217-231.]). To better understand the coordination chemistry of 3,3′-(diazene­diyl)dibenzoic acid, we have employed it in a reaction with Zn(OAc)2·2H2O in H2O and obtained the title three-dimensional supramolecular complex [Zn(ADB)(H2O)]n, (I)[link].

[Scheme 1]

Polymer (I)[link] crystallizes in the monoclinic space group P2/c and its asymmetric unit contains half a [Zn(ADB)(H2O)] unit, which sits across a twofold axis. As shown in Fig. 1[link], each ZnII cation adopts a distorted trigonal–bipyramidal coordination geometry, coordinated by four O atoms of bridging car­box­yl­ate groups from four ADB ligands (O1, O1ii, O2iii and O2iv, with the latter two atoms occupying the axial positions; see Fig. 1[link] for symmetry codes) and one O atom from a water mol­ecule (O1W). The Zn—O bond lengths range from 1.9503 (19) to 2.184 (2) Å. The mean Zn—O bond length in (I)[link] [2.047 (2) Å] is longer than that of the corresponding bond in [Zn(azobenzene-4,4′-dicarboxylate)(H2O)]n [2.069 (8) Å; Fu et al., 2009[Fu, F., Li, D.-S., Yang, X.-G., Zhang, C.-Q., Wu, Y.-P., Zhao, J. & Wang, E.-B. (2009). Inorg. Chem. Commun. 12, 657-659.]], and the N=N bond length [1.245 (5) Å] is slightly longer than that observed in [Zn(ADB)(EtOH)]n [1.209 (4) Å; Chen et al., 2008[Chen, Z.-F., Zhang, Z.-L., Tan, Y.-H., Tang, Y.-Z., Fun, H.-K., Zhou, Z.-Y., Abrahams, B. F. & Liang, H. (2008). CrystEngComm, 10, 217-231.]]. The O1—Zn1—O1ii and O2iii—Zn1—O2iv angles are 139.82 (13) and 174.46 (11)°, respectively, and the other O—Zn—O angles are in the range 87.23 (5)–110.09 (7)°, consistent with the distorted trigonal–bipyramidal configuration. The carboxyl­ate groups of the ADB ligand in (I)[link] only display a bridging coordination mode.

In (I)[link], each [Zn(H2O)] subunit is inter­linked by four bridging carboxyl­ate groups to form a one-dimensional [Zn(μ-COO)2(H2O)]n chain extending along the c axis (Fig. 2[link]), in which the [Zn(μ-COO)2(H2O)] units are arranged in an up–down fashion. These [Zn(μ-COO)2(H2O)]n chains are bridged by the ADB ligands themselves to form two-dimensional six-connected sheets lying parallel to the ac plane (Fig. 3[link]). Atom O2 of the carboxyl­ate group acts as an acceptor to inter­act with a coordinated water mol­ecule of an adjacent sheet, forming an inter­molecular hydrogen bond (O1W—H1W⋯O2v; see Table 1[link] for symmetry code). These hydrogen bonds connect the two-dimensional sheets, giving rise to a three-dimensional hydrogen-bonded supramolecular structure (Fig. 4[link]). Topologically (Wells, 1997[Wells, A. F. (1997). In Three-dimensional Nets and Polyhedra. New York: Wiley Interscience.]), if the ZnII centres are considered as nodes and the ADB ligands and hydrogen bonds are considered as linkers, the structure of (I)[link] can be specified by a new Schläfli symbol of 374175262 (Fig. 5[link]).

An inter­esting related structure was reported by Fu et al. (2009[Fu, F., Li, D.-S., Yang, X.-G., Zhang, C.-Q., Wu, Y.-P., Zhao, J. & Wang, E.-B. (2009). Inorg. Chem. Commun. 12, 657-659.]) based on 4,4′-(diazenedi­yl)dibenzoic acid instead of the 3,3′-(diazenedi­yl)dibenzoic acid used in this study. Fu's compound has the same formula as (I)[link] and crystallizes in the same space group with approximately the same unit-cell parameters, and the frameworks of the two structures are extremely similar. The ZnII cations in both structures adopt a distorted trigonal–bipyramidal coordination geometry and both structures possess two-dimensional fourfold-connected sheets in which the one-dimensional [Zn(μ-COO)2(H2O)]n chains are bridged by ADB ligands. However, it is inter­esting to note that, while the two-dimensional sheets of (I)[link] are linked by hydrogen bonds giving rise to a three-dimensional network with a 374175262 topology, in the structure reported by Fu et al. the sheets are bridged by another ligand arm in the [010] direction to form the three-dimensional network. This may be possible due to the longer arms of the linear 4,4′-(diazene­diyl)dibenzoic acid ligands. It should also be noted that the network of Fu's 4,4′-ADB structure is large enough to allow another equivalent network generated by the ADB arms in the [010] direction to inter­penetrate with that formed by the ZnII cations, giving rise to a twofold-inter­penetrated three-dimensional PtS framework. This suggests that ligand geometry plays an important role in the construction of coordination polymers with different topological structures, and it is expected that such ligand-dependent synthetic strategies may be applicable to other systems to produce other multidimensional coordination polymers with new topological structures.

[Figure 1]
Figure 1
The coordination environment of the ZnII atom in (I)[link], showing the atom-numbering scheme. Displacement ellipsoids are drawn at the 50% probability level. [Symmetry codes: (i) −x + 2, −y, −z + 1; (ii) −x + 1, y, −z + [{1\over 2}]; (iii) −x + 1, −y, −z + 1; (iv) x, −y, z − [{1\over 2}].]
[Figure 2]
Figure 2
A projection of the structure of (I)[link] along the a axis, showing a section of the one-dimensional [Zn(μ-COO)2(H2O)]n chain extending along the c axis. All H atoms and ADB ligands (except for the bridging carboxyl­ate groups) have been omitted for clarity.
[Figure 3]
Figure 3
A projection of the structure of (I)[link] along the b axis, showing the two-dimensional sheets extending parellel to the ac plane. All H atoms have been omitted for clarity.
[Figure 4]
Figure 4
A projection of the structure of (I)[link] along the a axis, showing the three-dimensional hydrogen-bonded structure. All C-bound H atoms have been omitted for clarity. Dashed lines indicate hydrogen bonds.
[Figure 5]
Figure 5
An illustration of the topological structure of (I)[link]. Spheres represent eight-connected nodes and lines represent ADB ligands and hydrogen-bond linkers (pink and blue lines, respectively, in the electronic version of the paper).

Experimental

A mixture of Zn(OAc)2·2H2O (11 mg, 0.05 mmol), H2ADB (7 mg, 0.025 mmol) and H2O (4 ml) was sealed in a 10 ml Pyrex glass tube and heated at 393 K for 4 d, then cooled to room temperature at a rate of 5 K h−1. Orange blocks of (I)[link] were collected, washed thoroughly with H2O and dried in air (yield 12 mg, 68% based on Zn). IR (KBr disc, ν, cm−1): 3350 (m), 3272 (m), 3070 (w), 2930 (w), 1651 (s), 1590 (s), 1552 (s), 1475 (m), 1430 (m), 1390 (s), 1315 (w), 1255 (w), 1222 (w), 1159 (m), 1110 (m), 1077 (m), 936 (w), 819 (m), 780 (m), 686 (m), 538 (w), 401 (w).

Crystal data
  • [Zn(C14H8N2O4)(H2O)]

  • Mr = 351.61

  • Monoclinic, P 2/c

  • a = 14.424 (4) Å

  • b = 6.3401 (16) Å

  • c = 7.234 (2) Å

  • β = 92.51 (3)°

  • V = 660.9 (3) Å3

  • Z = 2

  • Mo Kα radiation

  • μ = 1.89 mm−1

  • T = 296 K

  • 0.17 × 0.12 × 0.10 mm

Data collection
  • Bruker APEXII CCD area-detector diffractometer

  • Absorption correction: multi-scan (SADABS; Bruker, 2003[Bruker (2003). SADABS, SMART and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.]) Tmin = 0.740, Tmax = 0.834

  • 8726 measured reflections

  • 1172 independent reflections

  • 1085 reflections with I > 2σ(I)

  • Rint = 0.038

Refinement
  • R[F2 > 2σ(F2)] = 0.030

  • wR(F2) = 0.072

  • S = 1.10

  • 1172 reflections

  • 105 parameters

  • 1 restraint

  • H atoms treated by a mixture of independent and constrained refinement

  • Δρmax = 0.53 e Å−3

  • Δρmin = −0.34 e Å−3

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯AD—HH⋯ADAD—H⋯A
O1W—H1W⋯O2v0.82 (2)1.85 (2)2.639 (3)160 (4)
Symmetry code: (v) x, y-1, z.

The unique H atom (H1W) of the coordinated water mol­ecule (O1W) was located in a difference Fourier map and refined with a distance restraint [O—H = 0.83 (2) Å]. The second water H atom is generated by the crystallographic twofold axis. All other H atoms were placed in geometrically idealized positions, with C—H = 0.93 Å, and constrained to ride on their parent atoms, with Uiso(H) = 1.2Ueq(C).

Data collection: APEX2 (Bruker, 2005[Bruker (2005). APEX2. Bruker AXS Inc., Madison, Wisconsin, USA.]); cell refinement: SAINT (Bruker, 2003[Bruker (2003). SADABS, SMART and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.]); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); molecular graphics: XP (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]) and DIAMOND (Brandenburg, 1999[Brandenburg, K. (1999). DIAMOND. Crystal Impact GbR, Bonn, Germany.]); software used to prepare material for publication: SHELXTL (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]) and PLATON (Spek, 2009[Spek, A. L. (2009). Acta Cryst. D65, 148-155.]).

Supporting information


Comment top

In recent years, azobenzoic acid derivatives such as azobenzenedicarboxylic, azobenzenetricarboxylic and azobenzenetetracarboxylic acids have been employed as good bridging ligands for constructing various types of functional metal–organic frameworks (MOFs) (Cairns et al., 2008; Lee et al., 2008; Bhattacharya et al., 2011; Yang et al., 2011; Liu, Ren et al., 2011; Liu, Wan et al., 2011; Liu & Xu, 2009). For example, Yaghi and co-workers used 4,4'-azodibenzoic acid (4,4'-H2ADB) reacted with Tb(NO3)3.5H2O to form an interpenetrating network of {Tb2(ADB)3[(CH3)2SO]4.16[(CH3)2SO]}n with a large free volume (Reineke et al., 2000). Recently, Lu and co-workers reported three porous MOFs constructed from azobenzene-3,5,4'-tricarboxylic acid (H3ABTC) and Cd(NO3)2.4H2O or MnCl2.4H2O (Meng et al., 2011). Qiu and co-workers used 3,3',5,5'-azobenzenetetracarboxylic acid (H4ABTC) to construct three three-dimensional microporous MOFs with NbO and PtS topologies, which show hydrogen storage and luminescent properties (Xue et al., 2008). As for 3,3'-(diazenediyl)dibenzoic acid (H2ADB), Cudic et al. (1999) studied the host–guest chemistry between cyclo-bis-intercaland and ADB, and recently Chen et al. (2008) reported seven coordination polymers based on the assembly of H2ADB with Zn(OAc)2, PbI2, Co(OAc)2, Y(OAc)3, Sm(OAc)3 or Er(OAc)3, and/or 1,10-phenanthroline, which displayed considerable structural variety. Chen's ZnII ADB coordination polymer, [Zn(ADB)(EtOH)]n, was synthesized from Zn(OAc)2, pyridine and H2ADB in a mixture of solvents (DMF/H2O/EtOH) and shows a two-dimensional (4,4) network with Zn2 units serving as four-connecting square nodes (Chen et al., 2008). To better understand the coordination chemistry of 3,3'-(diazenediyl)dibenzoic acid, we have employed it in a reaction with Zn(OAc)2.2H2O in H2O and obtained the title three-dimensional coordination polymer [Zn(ADB)(H2O)]n, (I).

Polymer (I) crystallizes in the monoclinic space group P2/c and its asymmetric unit contains half a [Zn(ADB)(H2O)] unit. As shown in Fig. 1, each ZnII cation adopts a tetragonal–pyramidal coordination geometry, coordinated by four O atoms of bridging carboxylate groups from four ADB ligands (O1, O1ii, O1iii and O1iv; see Fig. 1 for symmetry codes) and one O atom from a water molecule (O1W). The Zn—O bond lengths range from 1.950 (3) to 2.184 (2) Å. The mean Zn—O bond length [2.047 (2) Å] in (I) is longer than the corresponding bond length in [Zn4(mip)4(dabco)(H2O)2] [2.038 (2) Å; mip is 5-methylisophthalate and dabco is diazabicyclo[2.2.2]octane; Chun et al., 2009], and the NN bond length [1.245 (5) Å] is slightly longer than that observed in [Zn(ADB)(EtOH)]n [1.209 (4) Å; Chen et al., 2008]. The O1—Zn1—O1ii and O2iii—Zn1—O2iv angles (see Fig. 1 for symmetry codes) are 139.82 (13) and 174.46 (11)°, respectively, and the other O—Zn—O angles are in the range 87.23 (5)–110.09 (7)°, consistent with the tetragonal–pyramidal configuration. The carboxylate groups of the ADB ligand in (I) only display a bridging coordination mode.

In (I), each [Zn(H2O)] subunit is interlinked by four bridging carboxylate groups to form a one-dimensional [Zn(µ-COO)4(H2O)]n chain extending along the c axis (Fig. 2), in which the [Zn(µ-COO)4(H2O)] units are arranged in an up–down fashion. These [Zn(µ-COO)4(H2O)]n chains are bridged by ADB ligands to form two-dimensional six-connected sheets extending along the ac plane (Fig. 3). Atom O2 of the carboxylate group acts as an acceptor to interact with a coordinated water molecule of an adjacent sheet, forming an intermolecular hydrogen bond (O1W—H1W···O2v; see Table 1 for symmetry code). These hydrogen bonds connect the two-dimensional sheets, giving rise to a three-dimensional hydrogen-bonded structure extending parallel to the bc plane (Fig. 4). Topologically (Wells, 1997), if the ZnII centres are considered as nodes and the ADB ligands and hydrogen bonds are considered as linkers, the structure of (I) can be specified by a new Schläfli symbol of 374175262 (Fig. 5).

An interesting related structure was reported by Fu et al. (2009), based on 4,4'-(diazenediyl)dibenzoic acid instead of the 3,3'-(diazenediyl)dibenzoic acid used in this study. Fu's compound has the same formula as (I) and crystallizes in the same space group with approximately the same unit-cell parameters, and the frameworks of the two structures are extremely similar. The ZnII cations in both structures adopt a tetragonal–pyramidal coordination geometry and both structures possess two-dimensional sixfold-connected sheets in which the one-dimensional [Zn(µ-COO)4(H2O)]n chains are bridged by ADB ligands. However, it is interesting to note that, while the two-dimensional sheets of (I) are linked by hydrogen bonds giving rise to a three-dimensional network with a 374175262 topology, in the structure reported by Fu et al. the sheets are bridged by another ligand arm in the [010] direction to form the three-dimensional network. This may be possible due to the longer arms of the linear 4,4'-(diazenediyl)dibenzoic acid ligands. It should also be noted that the network of Fu's 4,4'-ADB structure is large enough to allow another equivalent network generated by the ADB arms in the [010] direction to interpenetrate with that formed by the ZnII cations, giving rise to a twofold-interpenetrated three-dimensional PtS framework. This suggests that ligand geometry plays an important role in the construction of coordination polymers with different topological structuresm, and it is expected that such ligand-dependent synthetic strategies may be applicable to other systems to produce other multidimensional coordination polymers with new topological structures.

Related literature top

For related literature, see: Bhattacharya et al. (2011); Cairns et al. (2008); Chen et al. (2008); Chun et al. (2009); Cudic et al. (1999); Fu et al. (2009); Lee et al. (2008); Liu & Xu (2009); Liu, Ren, Zhu, Wang, Yan & Lang (2011); Liu, Wan, Ren & Lang (2011); Meng et al. (2011); Reineke et al. (2000); Wells (1997); Xue et al. (2008); Yang et al. (2011).

Experimental top

A mixture of Zn(OAc)2.2H2O (11 mg, 0.05 mmol), H2ADB ligand (7 mg, 0.025 mmol) and H2O (4 ml) was sealed in a 10 ml Pyrex glass tube and heated at 393 K for 4 d, then cooled to room temperature at a rate of 5 K h-1. Orange blocks of (I) were collected, washed thoroughly with H2O and dried in air (yield 12 mg, 68% based on Zn). Spectroscopic analysis: IR (KBr disc, ν, cm-1): 3350 (m), 3272 (m), 3070 (w), 2930 (w), 1651 (s), 1590 (s), 1552 (s), 1475 (m), 1430 (m), 1390 (s), 1315 (w), 1255 (w), 1222 (w), 1159 (m), 1110 (m), 1077 (m), 936 (w), 819 (m), 780 (m), 686 (m), 538 (w), 401 (w).

Refinement top

The H atom (H1W) of the coordinated water molecule (O1W) was located from a difference Fourier map and refined with the help of a distance restraint [O—H = 0.83 (2) Å]. The second water H atom is generated by the crystallographic twofold axis. All other H atoms were placed in geometrically idealized positions, with C—H = 0.93 Å, and constrained to ride on their parent atoms, with Uiso(H) = 1.2Ueq(C).

Computing details top

Data collection: APEX2 (Bruker, 2005); cell refinement: SAINT (Bruker, 2003); data reduction: SAINT (Bruker, 2003); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: XP (Sheldrick, 2008) and DIAMOND (Brandenburg, 1999); software used to prepare material for publication: SHELXTL (Sheldrick, 2008) and PLATON (Spek, 2009).

Figures top
Fig. 1. The coordination environment of the ZnII atom in (I), showing the atom-numbering scheme. Displacement ellipsoids are drawn at the 50% probability level. [Symmetry codes: (i) -x + 2, -y, -z + 1; (ii) -x + 1, y, -z + 1/2; (iii) -x + 1, -y, -z + 1; (iv) x, -y, z + 1/2.]

Fig. 2. A projection of the structure of (I) along the a axis, showing a section of the one-dimensional [Zn(µ-COO)4(H2O)]n chain extending along the c-axis direction. All H atoms and ADB ligands (except for the bridging carboxylate groups) have been omitted for clarity.

Fig. 3. A projection of the structure of (I) along the b axis, showing the two-dimensional sheets extending parellel to the ac plane. All H atoms have been omitted for clarity.

Fig. 4. A projection of the structure of (I) along the a axis, showing the three-dimensional hydrogen-bonded structure. All C-bound H atoms have been omitted for clarity. Dashed lines indicate hydrogen bonds.

Fig. 5. An illustration of the topological structure of (I). Spheres represent eight-connected nodes and lines represent ADB ligands and hydrogen-bond linkers (pink and blue lines, respectively, in the electronic version of the paper).
Poly[aqua[µ4-3,3'-(diazenediyl)dibenzoato]zinc] top
Crystal data top
[Zn(C14H8N2O4)(H2O)]F(000) = 356
Mr = 351.61Dx = 1.767 Mg m3
Monoclinic, P2/cMo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ycCell parameters from 3032 reflections
a = 14.424 (4) Åθ = 3.2–26.4°
b = 6.3401 (16) ŵ = 1.89 mm1
c = 7.234 (2) ÅT = 296 K
β = 92.51 (3)°Block, orange
V = 660.9 (3) Å30.17 × 0.12 × 0.10 mm
Z = 2
Data collection top
Bruker APEXII CCD area-detector
diffractometer
1172 independent reflections
Radiation source: fine-focus sealed tube1085 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.038
ϕ and ω scansθmax = 25.0°, θmin = 2.8°
Absorption correction: multi-scan
(SADABS; Bruker, 2003)
h = 1317
Tmin = 0.740, Tmax = 0.834k = 76
8726 measured reflectionsl = 88
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)] = 0.030Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.072H atoms treated by a mixture of independent and constrained refinement
S = 1.10 w = 1/[σ2(Fo2) + (0.0261P)2 + 1.0926P]
where P = (Fo2 + 2Fc2)/3
1172 reflections(Δ/σ)max < 0.001
105 parametersΔρmax = 0.53 e Å3
1 restraintΔρmin = 0.33 e Å3
Crystal data top
[Zn(C14H8N2O4)(H2O)]V = 660.9 (3) Å3
Mr = 351.61Z = 2
Monoclinic, P2/cMo Kα radiation
a = 14.424 (4) ŵ = 1.89 mm1
b = 6.3401 (16) ÅT = 296 K
c = 7.234 (2) Å0.17 × 0.12 × 0.10 mm
β = 92.51 (3)°
Data collection top
Bruker APEXII CCD area-detector
diffractometer
1172 independent reflections
Absorption correction: multi-scan
(SADABS; Bruker, 2003)
1085 reflections with I > 2σ(I)
Tmin = 0.740, Tmax = 0.834Rint = 0.038
8726 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0301 restraint
wR(F2) = 0.072H atoms treated by a mixture of independent and constrained refinement
S = 1.10Δρmax = 0.53 e Å3
1172 reflectionsΔρmin = 0.33 e Å3
105 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
xyzUiso*/Ueq
Zn10.50000.18449 (7)0.25000.02324 (16)
C10.62679 (17)0.0934 (5)0.4312 (4)0.0249 (6)
C20.72252 (18)0.1732 (5)0.4768 (4)0.0270 (6)
C30.7360 (2)0.3753 (5)0.5473 (4)0.0318 (7)
H30.68520.46210.56530.038*
C40.8251 (2)0.4480 (5)0.5908 (4)0.0360 (7)
H40.83380.58440.63570.043*
C50.9005 (2)0.3197 (5)0.5680 (4)0.0356 (7)
H50.96000.36900.59790.043*
C60.88782 (19)0.1155 (5)0.4999 (4)0.0306 (7)
C70.79900 (18)0.0438 (5)0.4523 (4)0.0284 (6)
H70.79060.09110.40380.034*
N10.96059 (16)0.0347 (4)0.4789 (4)0.0371 (6)
O10.61964 (12)0.0788 (3)0.3460 (3)0.0335 (5)
O20.55768 (12)0.2011 (3)0.4762 (3)0.0288 (5)
O1W0.50000.4950 (5)0.25000.0466 (9)
H1W0.521 (3)0.565 (5)0.338 (4)0.050 (11)*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Zn10.0140 (2)0.0218 (2)0.0337 (3)0.0000.00125 (17)0.000
C10.0173 (13)0.0326 (15)0.0247 (14)0.0006 (11)0.0005 (10)0.0031 (12)
C20.0189 (13)0.0355 (16)0.0266 (14)0.0032 (12)0.0011 (11)0.0003 (12)
C30.0229 (14)0.0321 (16)0.0403 (17)0.0015 (12)0.0006 (12)0.0018 (13)
C40.0305 (15)0.0324 (16)0.0446 (19)0.0064 (13)0.0038 (13)0.0048 (14)
C50.0210 (14)0.0447 (18)0.0406 (17)0.0108 (13)0.0046 (12)0.0010 (15)
C60.0191 (14)0.0425 (17)0.0299 (15)0.0018 (12)0.0018 (11)0.0003 (13)
C70.0185 (13)0.0362 (16)0.0305 (15)0.0050 (12)0.0010 (11)0.0049 (13)
N10.0162 (10)0.0496 (17)0.0451 (16)0.0040 (11)0.0020 (10)0.0042 (13)
O10.0156 (9)0.0421 (12)0.0429 (12)0.0034 (9)0.0013 (8)0.0163 (10)
O20.0188 (9)0.0324 (11)0.0354 (11)0.0041 (8)0.0024 (8)0.0056 (9)
O1W0.077 (3)0.0219 (16)0.039 (2)0.0000.0193 (18)0.000
Geometric parameters (Å, º) top
Zn1—O11.9503 (19)C3—H30.9300
Zn1—O1i1.9503 (19)C4—C51.374 (4)
Zn1—O1W1.969 (3)C4—H40.9300
Zn1—O2ii2.184 (2)C5—C61.394 (4)
Zn1—O2iii2.184 (2)C5—H50.9300
C1—O11.256 (3)C6—C71.389 (4)
C1—O21.263 (3)C6—N11.430 (4)
C1—C21.494 (4)C7—H70.9300
C2—C31.389 (4)N1—N1iv1.245 (5)
C2—C71.393 (4)O2—Zn1ii2.184 (2)
C3—C41.389 (4)O1W—H1W0.822 (18)
O1—Zn1—O1i139.82 (13)C4—C3—H3119.9
O1—Zn1—O1W110.09 (7)C5—C4—C3120.4 (3)
O1i—Zn1—O1W110.09 (7)C5—C4—H4119.8
O1—Zn1—O2ii93.45 (8)C3—C4—H4119.8
O1i—Zn1—O2ii88.46 (8)C4—C5—C6120.0 (3)
O1W—Zn1—O2ii87.23 (5)C4—C5—H5120.0
O1—Zn1—O2iii88.46 (8)C6—C5—H5120.0
O1i—Zn1—O2iii93.45 (8)C7—C6—C5119.8 (3)
O1W—Zn1—O2iii87.23 (5)C7—C6—N1115.4 (3)
O2ii—Zn1—O2iii174.46 (11)C5—C6—N1124.8 (3)
O1—C1—O2123.2 (2)C6—C7—C2120.2 (3)
O1—C1—C2117.3 (2)C6—C7—H7119.9
O2—C1—C2119.5 (3)C2—C7—H7119.9
C3—C2—C7119.4 (3)N1iv—N1—C6113.9 (3)
C3—C2—C1120.5 (2)C1—O1—Zn1121.72 (17)
C7—C2—C1120.1 (3)C1—O2—Zn1ii122.96 (17)
C2—C3—C4120.2 (3)Zn1—O1W—H1W123 (3)
C2—C3—H3119.9
O1—C1—C2—C3170.9 (3)C3—C2—C7—C60.8 (4)
O2—C1—C2—C37.9 (4)C1—C2—C7—C6178.0 (3)
O1—C1—C2—C710.3 (4)C7—C6—N1—N1iv179.4 (3)
O2—C1—C2—C7170.9 (3)C5—C6—N1—N1iv2.5 (5)
C7—C2—C3—C40.7 (4)O2—C1—O1—Zn16.7 (4)
C1—C2—C3—C4179.5 (3)C2—C1—O1—Zn1172.13 (18)
C2—C3—C4—C51.2 (5)O1i—Zn1—O1—C130.4 (2)
C3—C4—C5—C60.3 (5)O1W—Zn1—O1—C1149.6 (2)
C4—C5—C6—C71.2 (5)O2ii—Zn1—O1—C161.3 (2)
C4—C5—C6—N1176.9 (3)O2iii—Zn1—O1—C1124.0 (2)
C5—C6—C7—C21.7 (4)O1—C1—O2—Zn1ii96.4 (3)
N1—C6—C7—C2176.5 (3)C2—C1—O2—Zn1ii84.8 (3)
Symmetry codes: (i) x+1, y, z+1/2; (ii) x+1, y, z+1; (iii) x, y, z1/2; (iv) x+2, y, z+1.
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
O1W—H1W···O2v0.82 (2)1.85 (2)2.639 (3)160 (4)
Symmetry code: (v) x, y1, z.

Experimental details

Crystal data
Chemical formula[Zn(C14H8N2O4)(H2O)]
Mr351.61
Crystal system, space groupMonoclinic, P2/c
Temperature (K)296
a, b, c (Å)14.424 (4), 6.3401 (16), 7.234 (2)
β (°) 92.51 (3)
V3)660.9 (3)
Z2
Radiation typeMo Kα
µ (mm1)1.89
Crystal size (mm)0.17 × 0.12 × 0.10
Data collection
DiffractometerBruker APEXII CCD area-detector
diffractometer
Absorption correctionMulti-scan
(SADABS; Bruker, 2003)
Tmin, Tmax0.740, 0.834
No. of measured, independent and
observed [I > 2σ(I)] reflections
8726, 1172, 1085
Rint0.038
(sin θ/λ)max1)0.595
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.030, 0.072, 1.10
No. of reflections1172
No. of parameters105
No. of restraints1
H-atom treatmentH atoms treated by a mixture of independent and constrained refinement
Δρmax, Δρmin (e Å3)0.53, 0.33

Computer programs: APEX2 (Bruker, 2005), SAINT (Bruker, 2003), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), XP (Sheldrick, 2008) and DIAMOND (Brandenburg, 1999), SHELXTL (Sheldrick, 2008) and PLATON (Spek, 2009).

Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
O1W—H1W···O2i0.822 (18)1.85 (2)2.639 (3)160 (4)
Symmetry code: (i) x, y1, z.
 

Acknowledgements

This work was supported by the Research Start-Up Fund for New Staff of Anyang Normal University (grant No. 308772).

References

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