Synthesis and crystal structure of catena-poly[[aqua­zinc(II)]-bis­[μ2-4-(phenyl­diazen­yl)benzoato-κ2O:O′]]

Huang, Y.-Y.; Zhang, B.-G.; Sun, Q.-Z.

doi:10.1107/S2056989026005177

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Volume 82| Part 7| July 2026|

https://doi.org/10.1107/S2056989026005177

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Synthesis and crystal structure of catena-poly[[aquazinc(II)]-bis[μ₂-4-(phenyldiazenyl)benzoato-κ²O:O′]]

Yu-Ying Huang,^a Bing-Guang Zhang ^a ^* and Qiao-Zhen Sun ^b

^aKey Laboratory of Catalysis and Materials Sciences of the State Ethnic Affairs Commission & Ministry of Education, College of Chemistry and Material Science, South-Central Minzu University, Wuhan, 430074, People's Republic of China, and ^bSchool of Materials Science and Engineering, Central South University, Changsha, 410083, People's Republic of China
^*Correspondence e-mail: [email protected]

Edited by X. Hao, Institute of Chemistry, Chinese Academy of Sciences (Received 18 March 2026; accepted 16 May 2026; online 5 June 2026)

In the title compound, [Zn(C₁₃H₉N₂O₂)₂(H₂O)]_n or [Zn(pba)₂(H₂O)]_n (pba⁻ = 4-(phenyldiazenyl)benzoate, the Zn²⁺ ions are coordinated by one water molecule and four oxygen atoms from four different pba⁻ ligands to form a [ZnO₅] trigonal bipyramid. The Zn ion and the water O atom lie on a twofold axis. The trigonal bipyramids are bridged by the pba⁻ ligands, extending the structure into chains propagating along the b-axis direction. The chains are connected through hydrogen-bonding interactions.

Keywords: crystal structure; zinc; 4-(phenyldiazenyl)benzoic acid; hydrogen bonds..

CCDC reference: 2537431

1. Chemical context

Azobenzene, as a classical photoswitchable molecule, has gained great attention in designing stimuli-responsive supramolecular system due to its unique photochromic properties arising from reversible E and Z geometric isomerism (Feng et al., 2025 ; Golzani et al., 2026 ; Hao et al., 2017 ). In recent years, metal–organic frameworks (MOFs) and their derivatives have become widely used in many fields such as separation, catalysis, detection and electrochemical reduction (Liang et al., 2024 ; Zhao et al., 2022 , 2026 ; Zhong et al., 2025 ). Incorporating azobenzene derivatives into MOFs represents a frontier strategy for constructing stimuli responsive systems in materials science. For example, Nitschke and co-workers successfully developed light-responsive metal–organic capsules by incorporating azobenzene-based ligands (Ghosh et al., 2026 ) while Tadjarodi and co-workers fabricated a sacrificial nanozyme-based MOF capable of detecting and quantifying Hg²⁺ ions in aqueous solutions by using an azobenzene-4,4-dicarboxylate ligand (Golzani et al., 2026). However, theoretically, the molecular motion will be certainly restricted by steric constraints and lattice strain in crystalline MOFs. To supply more examples of functional compounds incorporation by azobenzene derivatives, the title compound, (1), with a one-dimensional chain structure, was obtained.

2. Structural commentary

The asymmetric unit of (1) one Zn ion (site symmetry 2), one pba⁻ anion and one water molecule (O atom site symmetry 2) (Fig. 1). The Zn—O bond lengths are in the range 1.954 (5)–2.150 (3) Å (Table 1). All the data are comparable to those reported for other related Zn^II–polycarboxylate compounds (Gu et al., 2023 ; Liu et al., 2025 ; Zhao et al., 2024 ). Each Zn center is five-coordinated by four oxygen from four different pba⁻ anions and one coordinated water molecule, forming a trigonal–bipyramidal geometry. The equatorial plane is occupied by atoms O1, O1ⁱ and O3. The pba⁻ ligand bridges two Zn^II ions through its carboxyl O atoms, and two Zn^II ions are bridged by two pba⁻ ligands to form a binuclear Zn₂(COO)₂ unit. The two Zn^IIions and the two carboxyl carbon atoms are in the same plane. The neighboring Zn₂(COO)₂ unit is distorted and the angle between the binuclear units is 77.3 (1)° (the plane is defined by two Zn^II ions and two carboxyl carbon atoms).

Table 1
Selected geometric parameters (Å, °)

Zn1—O1	1.964 (3)	Zn1—O2ⁱⁱⁱ	2.150 (3)
Zn1—O1ⁱ	1.964 (3)	Zn1—O3	1.954 (5)
Zn1—O2ⁱⁱ	2.150 (3)

O1—Zn1—O1ⁱ	142.3 (2)	O3—Zn1—O1ⁱ	108.85 (11)
O1—Zn1—O2ⁱⁱⁱ	87.11 (12)	O3—Zn1—O1	108.85 (10)
O1ⁱ—Zn1—O2ⁱⁱⁱ	94.66 (13)	O3—Zn1—O2ⁱⁱⁱ	87.26 (9)
O1ⁱ—Zn1—O2ⁱⁱ	87.11 (12)	O3—Zn1—O2ⁱⁱ	87.26 (9)
O1—Zn1—O2ⁱⁱ	94.66 (13)	C1—O1—Zn1	121.4 (3)
O2ⁱⁱⁱ—Zn1—O2ⁱⁱ	174.51 (18)	C1—O2—Zn1ⁱⁱ	125.4 (3)
Symmetry codes: (i) $[-x+1, y, -z+{\script{3\over 2}}]$ ; (ii) ; (iii) $[x, -y+1, z+{\script{1\over 2}}]$ .

Figure 1
The extended asymmetric unit of (1) showing the coordination environment of the Zn²⁺ cation and the ligand. Displacement ellipsoids are drawn at the 30% probability level. [Symmetry codes: (A) −x + 1, −y + 1, −z + 1; (B)−x + 1, y, −z + $[{3\over 2}]$ ; (C) x, −y + 1, z + $[{1\over 2}]$ .]

3. Supramolecular features

In the crystal, The units are extended along the c-axis direction, generating a one-dimensional zigzag chain (Fig. 2). The ligand hangs along the chain towards different directions (Fig. 3). O—H⋯O hydrogen bonds are observed (Table 2). The packing is shown in Fig. 4.

Table 2
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O3—H3⋯O2^iv	0.87	1.78	2.588 (4)	154
Symmetry code: (iv) $[-x+1, y+1, -z+{\script{3\over 2}}]$ .

Figure 2
The one-dimensional zigzag chain.

Figure 3
The one-dimensional chain constructed by Zn^II ions and the carboxyl groups.

Figure 4
Packing diagram of (1), showing hydrogen-bonding interactions (dashed lines).

4. Synthesis and crystallization

A mixture of Zn(NO₃)₂·6H₂O (29.5 mg, 0.1 mmol) and pba (45.2 mg, 0.2 mmol) in 5 mL DMF was sealed in a Teflon lined autoclave and heated to 393 K for 48 h, then gradually cooled down to room temperature. Pale-yellow block-shaped crystals were obtained.

5. Refinement

Crystal data, data collection and structure refinement details are summarized in Table 3. The hydrogen atom of the coordinated water molecule was located from a difference-Fourier map, and refined using a riding model with isotropic displacement parameters U_iso(H) = 1.5U_eq(O). C-bound H atoms were positioned geometrically (C—H = 0.95 Å) and refined with as riding with U_iso(H) = 1.2U_eq(C).

Table 3
Experimental details

Crystal data
Chemical formula	[Zn(C₁₃H₉N₂O₂)₂(H₂O)]
M_r	533.83
Crystal system, space group	Monoclinic, C2/c
Temperature (K)	100
a, b, c (Å)	51.1233 (13), 6.1213 (2), 7.2534 (3)
β (°)	90.788 (3)
V (Å³)	2269.68 (13)
Z	4
Radiation type	Cu Kα
μ (mm⁻¹)	1.91
Crystal size (mm)	0.35 × 0.34 × 0.34

Data collection
Diffractometer	ROD, Synergy Custom DW system, HyPix
Absorption correction	Multi-scan (CrysAlis PRO; Rigaku Oxford Diffraction, 2023 )
T_min, T_max	0.683, 1.000
No. of measured, independent and observed [I > 2σ(I)] reflections	12079, 2310, 1997
R_int	0.074
(sin θ/λ)_max (Å⁻¹)	0.629

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.064, 0.188, 1.09
No. of reflections	2310
No. of parameters	164
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.98, −0.79
Computer programs: CrysAlis PRO (Rigaku OD, 2023), SHELXT (Sheldrick, 2015a ), SHELXL2018/3 (Sheldrick, 2015b ) and OLEX2 (Dolomanov et al., 2009 ).

Supporting information

CCDC reference: 2537431

Crystal structure: contains datablock I. DOI: https://doi.org/10.1107/S2056989026005177/nx2033sup1.cif

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S2056989026005177/nx2033Isup2.hkl

checkCIF report

Computing details top

catena-Poly[[aquazinc(II)]-bis[µ₂-4-(phenyldiazenyl)benzoato-κ²O:O']] top

Crystal data top

[Zn(C₁₃H₉N₂O₂)₂(H₂O)]	F(000) = 1096
M_r = 533.83	D_x = 1.562 Mg m⁻³
Monoclinic, C2/c	Cu Kα radiation, λ = 1.54184 Å
a = 51.1233 (13) Å	Cell parameters from 5128 reflections
b = 6.1213 (2) Å	θ = 1.7–75.3°
c = 7.2534 (3) Å	µ = 1.91 mm⁻¹
β = 90.788 (3)°	T = 100 K
V = 2269.68 (13) Å³	Block, colourless
Z = 4	0.35 × 0.34 × 0.34 mm

Data collection top

ROD, Synergy Custom DW system, HyPix diffractometer	2310 independent reflections
Radiation source: Rotating-anode X-ray tube, Rigaku (Cu) X-ray Source	1997 reflections with I > 2σ(I)
Mirror monochromator	R_int = 0.074
Detector resolution: 10.0000 pixels mm^-1	θ_max = 75.8°, θ_min = 1.7°
ω scans	h = −63→63
Absorption correction: multi-scan (CrysAlisPro; Rigaku Oxford Diffraction, 2023)	k = −7→7
T_min = 0.683, T_max = 1.000	l = −9→9
12079 measured reflections

Refinement top

Refinement on F²	Primary atom site location: dual
Least-squares matrix: full	Hydrogen site location: mixed
R[F² > 2σ(F²)] = 0.064	H-atom parameters constrained
wR(F²) = 0.188	w = 1/[σ²(F_o²) + (0.0833P)² + 14.3419P] where P = (F_o² + 2F_c²)/3
S = 1.09	(Δ/σ)_max < 0.001
2310 reflections	Δρ_max = 0.98 e Å⁻³
164 parameters	Δρ_min = −0.78 e Å⁻³
0 restraints

Special details top

Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes.

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

	x	y	z	U_iso*/U_eq
Zn1	0.500000	0.68636 (12)	0.750000	0.0348 (3)
O1	0.46580 (5)	0.5827 (6)	0.6597 (5)	0.0429 (8)
O2	0.48302 (5)	0.2968 (5)	0.5191 (4)	0.0395 (7)
O3	0.500000	1.0056 (8)	0.750000	0.0614 (15)
H3	0.501450	1.091918	0.844860	0.092*
N1	0.35958 (6)	0.1029 (6)	0.4436 (5)	0.0366 (8)
N2	0.35633 (7)	−0.0988 (6)	0.4260 (5)	0.0380 (8)
C1	0.46353 (8)	0.4063 (8)	0.5720 (6)	0.0363 (9)
C2	0.40772 (8)	0.0371 (7)	0.4283 (6)	0.0363 (9)
H2	0.405238	−0.105117	0.378553	0.044*
C3	0.29970 (9)	−0.4379 (8)	0.2927 (7)	0.0428 (10)
H3A	0.296645	−0.578410	0.241022	0.051*
C4	0.28344 (8)	−0.0956 (9)	0.4070 (7)	0.0437 (11)
H4	0.269101	−0.003491	0.435632	0.052*
C5	0.43271 (8)	0.1173 (8)	0.4591 (7)	0.0377 (10)
H5	0.447401	0.030593	0.427714	0.045*
C6	0.43656 (8)	0.3233 (7)	0.5352 (6)	0.0353 (9)
C7	0.38625 (8)	0.1666 (7)	0.4710 (6)	0.0345 (9)
C8	0.41509 (8)	0.4531 (7)	0.5779 (6)	0.0357 (9)
H8	0.417655	0.593238	0.631425	0.043*
C9	0.27874 (9)	−0.3010 (9)	0.3321 (7)	0.0461 (11)
H9	0.261314	−0.347783	0.307790	0.055*
C10	0.30859 (8)	−0.0238 (8)	0.4405 (6)	0.0381 (10)
H10	0.311607	0.117081	0.491508	0.046*
C11	0.32956 (8)	−0.1596 (7)	0.3988 (6)	0.0366 (10)
C12	0.38991 (8)	0.3773 (8)	0.5420 (6)	0.0369 (10)
H12	0.375247	0.467940	0.565622	0.044*
C13	0.32514 (9)	−0.3678 (8)	0.3294 (7)	0.0399 (10)
H13	0.339470	−0.462513	0.306996	0.048*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Zn1	0.0210 (4)	0.0272 (4)	0.0562 (6)	0.000	0.0029 (3)	0.000
O1	0.0247 (14)	0.0444 (19)	0.060 (2)	−0.0063 (13)	0.0040 (12)	−0.0118 (15)
O2	0.0221 (13)	0.0465 (19)	0.0500 (18)	0.0000 (12)	0.0034 (12)	0.0032 (14)
O3	0.096 (4)	0.027 (2)	0.061 (3)	0.000	−0.017 (3)	0.000
N1	0.0252 (16)	0.0325 (19)	0.052 (2)	−0.0029 (14)	0.0021 (14)	−0.0003 (16)
N2	0.0267 (17)	0.036 (2)	0.052 (2)	−0.0029 (15)	0.0044 (14)	0.0000 (16)
C1	0.0256 (19)	0.039 (2)	0.044 (2)	−0.0017 (17)	0.0039 (16)	0.0033 (19)
C2	0.0277 (19)	0.032 (2)	0.049 (2)	−0.0001 (16)	0.0024 (17)	−0.0010 (18)
C3	0.038 (2)	0.036 (2)	0.054 (3)	−0.0103 (19)	0.0004 (19)	0.001 (2)
C4	0.029 (2)	0.049 (3)	0.054 (3)	0.0010 (19)	0.0047 (18)	0.005 (2)
C5	0.0241 (19)	0.037 (2)	0.053 (3)	0.0038 (17)	0.0060 (17)	0.0018 (19)
C6	0.0241 (19)	0.035 (2)	0.047 (2)	−0.0017 (16)	0.0042 (16)	0.0042 (18)
C7	0.0231 (18)	0.034 (2)	0.046 (2)	−0.0031 (16)	0.0027 (16)	0.0051 (17)
C8	0.0269 (19)	0.034 (2)	0.047 (2)	−0.0034 (16)	0.0026 (16)	0.0004 (18)
C9	0.029 (2)	0.056 (3)	0.053 (3)	−0.011 (2)	0.0004 (19)	0.003 (2)
C10	0.0284 (19)	0.037 (2)	0.049 (2)	−0.0006 (17)	0.0032 (17)	0.0022 (19)
C11	0.028 (2)	0.036 (2)	0.046 (3)	−0.0060 (16)	0.0035 (17)	0.0014 (18)
C12	0.0259 (19)	0.036 (2)	0.049 (3)	0.0034 (16)	0.0058 (17)	0.0035 (19)
C13	0.034 (2)	0.032 (2)	0.054 (3)	−0.0024 (17)	0.0068 (19)	0.0020 (19)

Geometric parameters (Å, º) top

Zn1—O1	1.964 (3)	C3—C9	1.393 (7)
Zn1—O1ⁱ	1.964 (3)	C3—C13	1.392 (6)
Zn1—O2ⁱⁱ	2.150 (3)	C4—H4	0.9500
Zn1—O2ⁱⁱⁱ	2.150 (3)	C4—C9	1.389 (7)
Zn1—O3	1.954 (5)	C4—C10	1.377 (6)
O1—C1	1.258 (6)	C5—H5	0.9500
O2—C1	1.265 (5)	C5—C6	1.390 (6)
O3—H3	0.8700	C6—C8	1.393 (6)
O3—H3ⁱ	0.8700	C7—C12	1.400 (6)
N1—N2	1.252 (5)	C8—H8	0.9500
N1—C7	1.430 (5)	C8—C12	1.389 (6)
N2—C11	1.429 (5)	C9—H9	0.9500
C1—C6	1.490 (6)	C10—H10	0.9500
C2—H2	0.9500	C10—C11	1.393 (6)
C2—C5	1.384 (6)	C11—C13	1.388 (6)
C2—C7	1.392 (6)	C12—H12	0.9500
C3—H3A	0.9500	C13—H13	0.9500

O1—Zn1—O1ⁱ	142.3 (2)	C10—C4—C9	120.9 (4)
O1—Zn1—O2ⁱⁱⁱ	87.11 (12)	C2—C5—H5	119.6
O1ⁱ—Zn1—O2ⁱⁱⁱ	94.66 (13)	C2—C5—C6	120.8 (4)
O1ⁱ—Zn1—O2ⁱⁱ	87.11 (12)	C6—C5—H5	119.6
O1—Zn1—O2ⁱⁱ	94.66 (13)	C5—C6—C1	120.4 (4)
O2ⁱⁱⁱ—Zn1—O2ⁱⁱ	174.51 (18)	C5—C6—C8	119.9 (4)
O3—Zn1—O1ⁱ	108.85 (11)	C8—C6—C1	119.7 (4)
O3—Zn1—O1	108.85 (10)	C2—C7—N1	124.5 (4)
O3—Zn1—O2ⁱⁱⁱ	87.26 (9)	C2—C7—C12	120.3 (4)
O3—Zn1—O2ⁱⁱ	87.26 (9)	C12—C7—N1	115.1 (4)
C1—O1—Zn1	121.4 (3)	C6—C8—H8	120.0
C1—O2—Zn1ⁱⁱ	125.4 (3)	C12—C8—C6	119.9 (4)
Zn1—O3—H3	127.4	C12—C8—H8	120.0
Zn1—O3—H3ⁱ	127.408 (2)	C3—C9—H9	120.1
H3—O3—H3ⁱ	105.2	C4—C9—C3	119.7 (4)
N2—N1—C7	114.1 (4)	C4—C9—H9	120.1
N1—N2—C11	113.4 (4)	C4—C10—H10	120.3
O1—C1—O2	122.7 (4)	C4—C10—C11	119.4 (4)
O1—C1—C6	117.5 (4)	C11—C10—H10	120.3
O2—C1—C6	119.8 (4)	C10—C11—N2	123.6 (4)
C5—C2—H2	120.3	C13—C11—N2	116.1 (4)
C5—C2—C7	119.4 (4)	C13—C11—C10	120.3 (4)
C7—C2—H2	120.3	C7—C12—H12	120.2
C9—C3—H3A	120.2	C8—C12—C7	119.7 (4)
C13—C3—H3A	120.2	C8—C12—H12	120.2
C13—C3—C9	119.6 (4)	C3—C13—H13	120.0
C9—C4—H4	119.5	C11—C13—C3	120.0 (4)
C10—C4—H4	119.5	C11—C13—H13	120.0

Zn1—O1—C1—O2	−7.8 (6)	C2—C5—C6—C8	−1.3 (7)
Zn1—O1—C1—C6	170.5 (3)	C2—C7—C12—C8	−3.0 (7)
Zn1ⁱⁱ—O2—C1—O1	−95.8 (5)	C4—C10—C11—N2	179.1 (4)
Zn1ⁱⁱ—O2—C1—C6	86.0 (5)	C4—C10—C11—C13	−1.9 (7)
O1—C1—C6—C5	−172.2 (4)	C5—C2—C7—N1	179.3 (4)
O1—C1—C6—C8	7.6 (6)	C5—C2—C7—C12	0.8 (7)
O2—C1—C6—C5	6.1 (7)	C5—C6—C8—C12	−0.8 (7)
O2—C1—C6—C8	−174.0 (4)	C6—C8—C12—C7	2.9 (7)
N1—N2—C11—C10	−17.8 (7)	C7—N1—N2—C11	180.0 (4)
N1—N2—C11—C13	163.1 (4)	C7—C2—C5—C6	1.3 (7)
N1—C7—C12—C8	178.5 (4)	C9—C3—C13—C11	−2.3 (7)
N2—N1—C7—C2	18.8 (6)	C9—C4—C10—C11	−0.2 (7)
N2—N1—C7—C12	−162.7 (4)	C10—C4—C9—C3	1.0 (7)
N2—C11—C13—C3	−177.8 (4)	C10—C11—C13—C3	3.1 (7)
C1—C6—C8—C12	179.3 (4)	C13—C3—C9—C4	0.2 (7)
C2—C5—C6—C1	178.5 (4)

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

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O3—H3···O2^iv	0.87	1.78	2.588 (4)	154

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

Acknowledgements

This work was financially supported by the National Natural Science Foundation of China (No. 21271189) and the Natural Science Foundation of Hunan Province of China (No. 2023 J J30685) for their financial support.

Funding information

This work was financially supported by the National Natural Science Foundation of China (No. 21271189) and the Natural Science Foundation of Hunan Province of China (No. 2023 J J30685).

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