BY 4.0 license Open Access Pre-published online by De Gruyter (O) September 23, 2021

The crystal structure of poly[(μ4-4,4′-(azanediylbis(methylene))dibenzoato-κ4O:N:O′:Oʺ)zinc(II)], C16H13NO4Zn

Hai-Lin Chen ORCID logo, Dong-Mei Yao, Yan-Ping Wang and Ya-Xin Lao

Abstract

C16H13NO4Zn, triclinic, P1 (no. 2), a = 7.5223(6) Å, b = 8.0977(8) Å, c = 11.7739(11) Å, α = 76.410(8), β = 75.495(8), γ = 75.902(8), V = 661.76(11) Å3, Z = 2, Rgt(F) = 0.0532, wRref(F2) = 0.1041, T = 293(2) K.

CCDC no.: 2108739

A part of the title coordination-polymeric structure is shown in the figure. Table 1 contains crystallographic data and Table 2 contains the list of the atoms including atomic coordinates and displacement parameters.

Table 1:

Data collection and handling.

Crystal:Colorless block
Size:0.30 × 0.20 × 0.20 mm
Wavelength:Mo Kα radiation (0.71073 Å)
μ:1.87 mm−1
Diffractometer, scan mode:φ and ω
θmax, completeness:26.4°, >99%
N(hkl)measured, N(hkl)unique, Rint:5365, 2700, 0.043
Criterion for Iobs, N(hkl)gt:Iobs > 2σ(Iobs), 2146
N(param)refined:199
Programs:CrysAlisPRO [1], Diamond [2], SHELX [3, 4]
Table 2:

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

AtomxyzUiso*/Ueq
Zn10.39487 (7)−0.04929 (6)0.17140 (4)0.02808 (17)
O10.5265 (4)0.0752 (4)0.2345 (2)0.0329 (7)
O20.2504 (4)0.1432 (4)0.3528 (3)0.0415 (8)
O30.7020 (4)0.8984 (3)0.9672 (2)0.0315 (7)
O40.5634 (4)0.7367 (3)1.1270 (2)0.0312 (7)
N10.8378 (4)0.1459 (4)0.7303 (3)0.0242 (8)
H10.9049270.0597830.6803040.029*
C10.4206 (6)0.1377 (5)0.3234 (4)0.0278 (10)
C20.5157 (6)0.2007 (5)0.3991 (3)0.0245 (9)
C30.7092 (6)0.1910 (5)0.3717 (4)0.0321 (10)
H30.7792580.1573770.3007970.039*
C40.7978 (6)0.2305 (5)0.4483 (4)0.0334 (10)
H40.9267550.2236420.4287740.040*
C50.6950 (6)0.2805 (5)0.5543 (3)0.0277 (10)
C60.5020 (6)0.2985 (5)0.5796 (3)0.0287 (10)
H60.4313270.3387370.6481970.034*
C70.4142 (6)0.2567 (5)0.5031 (3)0.0294 (10)
H70.2848420.2664420.5219040.035*
C80.7944 (6)0.3092 (5)0.6429 (4)0.0325 (10)
H8A0.9096780.3478620.6006600.039*
H8B0.7156570.3989910.6853100.039*
C90.9766 (6)0.1532 (5)0.8002 (3)0.0270 (9)
H9A1.0953610.1651280.7461400.032*
H9B0.9964920.0455700.8568500.032*
C100.9098 (5)0.3033 (5)0.8667 (3)0.0238 (9)
C110.9651 (6)0.4602 (5)0.8147 (3)0.0261 (9)
H111.0529790.4689400.7433300.031*
C120.8907 (5)0.6027 (5)0.8680 (3)0.0246 (9)
H120.9276270.7073770.8312740.030*
C130.7622 (5)0.5936 (5)0.9750 (3)0.0209 (8)
C140.7127 (6)0.4337 (5)1.0307 (3)0.0251 (9)
H140.6292130.4235681.1039150.030*
C150.7883 (6)0.2906 (5)0.9767 (3)0.0262 (9)
H150.7569320.1841621.0149630.031*
C160.6699 (5)0.7527 (5)1.0257 (4)0.0234 (9)

  1. Ueq is equivalent isotropic displacement parameters. Uiso∗ is isotropic displacement parameters. So ‘∗’ is Uiso∗.

Source of material

All reagents and chemicals were purchased from commercial sources and used without further purification. The starting material 4,4′-(azanediylbis(methylene))dibenzoic acid was synthesized following the literature procedures [5]. A mixture of Zn(NO3)2·6H2O (0.05 mmol), 4,4′-(azanediylbis(methylene))dibenzoic acid (0.05 mmol), N,N-dimethylacetamide (0.5 mL), ethanol(3  mL), and H2O (3  mL) was sealed in a 20 mL vial and heated at 363 K for two days. Colorless block crystals were collected. IR spectra (potassium bromide pellet) were recorded on a Nicolet 6700. IR (v/cm−1): 3433, 3238, 3049, 2974, 2929, 2869, 1612, 1597, 1545, 1509, 1403, 1371, 1356, 1308, 1200, 1186, 1066, 1024, 908, 881, 860, 816, 801, 777, 768, 719, 707, 669, 575, 540, 464.

Experimental details

H atoms were placed in calculated positions and were included in the refinement in the riding model approximation, with Uiso(H) set to 1.2 Ueq(C). The nitrogen-bound H atoms were located on a difference Fourier map.

Comment

In recent years, 4,4′-(azanediylbis(methylene))dibenzoic acid and its analogues have been widely applied in the formation of zinc coordination polymers [6], [7], [8], [9]. Some zinc complexes have drawn tremendous attention because of their potential applications in gas separation [8] and chemical sensor [9]. To further explore this area, we used 4,4′-(azanediylbis(methylene))dibenzoic acid to prepare a new zinc coordination polymer.

The asymmetric unit consists of one zinc cation and one 4,4′-(azanediylbis(methylene))dibenzoate ligand. The zinc(II) ion is surrounded by one nitrogen atom and three oxygen atoms from four different ligands. Its coordination geometry is a slightly distorted tetrahedron. The Zn—O bond lengths range from 1.983(3) to 1.977(3) Å. The Zn—N bond is 2.059(3) Å, and are in the expected ranges [10]. Adjacent ligands have intramolecular N1—H1⃛O2 hydrogen bond of length 2.384 Å. The zinc coordination polymer is extended to a two dimensional layer along the bc plane. There are weak ππ interactions between C10—C15 phenyl rings from adjacent layers. The centroid-centroid distance is 3.745(2) Å. Together with the ππ stacking interactions a three-dimensional network is obtained.


Corresponding author: Dong-Mei Yao, School of Chemical and Biological Engineering, Hechi University, Yizhou, Guangxi546300, China, E-mail:

Funding source: Guangxi Natural Science Foundation of China

Award Identifier / Grant number: 2020GXNSFBA297138

Funding source: 2021 High-level Talents Scientific Research Startup Fund of Hechi University

Award Identifier / Grant number: 2021GCC021

  1. Author contributions: All the authors have accepted responsibility for the entire content of this submitted manuscript and approved submission.

  2. Research funding: This work was financially supported by Guangxi Natural Science Foundation of China (No. 2020GXNSFBA297138) and 2021 High-level Talents Scientific Research Startup Fund of Hechi University (No. 2021GCC021).

  3. Conflict of interest statement: The authors declare no conflicts of interest regarding this article.

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Received: 2021-08-20
Published Online: 2021-09-23

© 2021 Hai-Lin Chen et al., published by De Gruyter, Berlin/Boston

This work is licensed under the Creative Commons Attribution 4.0 International License.